#\#CIF_1.1
 
#  CIF produced by WinGX routine CIF_UPDATE
#  Created on 2005-07-21 at 11:46:58
#  Using CIFtbx version 2.6.2 16 Jun 1998
 
#  Dictionary name : cif_core.dic
#  Dictionary vers : 2.3
#  Request file    : c:\wingx\files\archive.dat
#  CIF files read  : ljf131 sortav struct
 
 
data_ljf131
 
_audit_creation_date                    2005-07-21T11:46:58-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
_audit_conform_dict_name                cif_core.dic
_audit_conform_dict_version             2.3
_audit_conform_dict_location            ftp://ftp.iucr.org/pub/cif_core.dic
_publ_requested_category                FO
 
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
 
_chemical_name_systematic
     1,4,7,110-isopropylaminecarbonyloxyethyl-1,4,7,10-tetraazacyclododecane
_chemical_formula_moiety                'C32 H64 N8 O8'
_chemical_formula_sum                   'C32 H64 N8 O8'
_chemical_formula_weight                688.91
_chemical_compound_source               'synthesis as described'
 
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
 
_space_group_crystal_system             monoclinic
_space_group_name_H-M_alt               'P 21/a'
_space_group_name_Hall                  '-P 2yab'
_space_group_IT_number                  14
loop_
    _space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
 
_cell_length_a                          12.8699(5)
_cell_length_b                          9.5994(4)
_cell_length_c                          17.0767(8)
_cell_angle_alpha                       90
_cell_angle_beta                        111.043(2)
_cell_angle_gamma                       90
_cell_volume                            1969.02(15)
_cell_formula_units_Z                   2
_cell_measurement_temperature           291(2)
_cell_measurement_reflns_used           2981
_cell_measurement_theta_max             20.587
_cell_measurement_theta_min             2.477
_cell_measurement_wavelength            0.71073
 
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
 
_exptl_crystal_description              'irregular shape'
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.39
_exptl_crystal_size_mid                 0.35
_exptl_crystal_size_min                 0.25
_exptl_crystal_density_diffrn           1.162
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    752
_exptl_special_details
;
 crystal specimen diffracted very poorly above 20 deg
;
 
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu           0.084
_exptl_absorpt_correction_type          none
 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
 
_diffrn_ambient_temperature             291(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_reflns_av_R_equivalents         0.036
_diffrn_reflns_av_unetI/netI            0.0344
_diffrn_reflns_number                   17875
_diffrn_reflns_limit_h_min              -15
_diffrn_reflns_limit_h_max              15
_diffrn_reflns_limit_k_min              -11
_diffrn_reflns_limit_k_max              11
_diffrn_reflns_limit_l_min              -21
_diffrn_reflns_limit_l_max              21
_diffrn_reflns_theta_min                1.28
_diffrn_reflns_theta_max                26.14
_diffrn_reflns_theta_full               26.14
_diffrn_measured_fraction_theta_full
                                        0.999
_diffrn_measured_fraction_theta_max
                                        0.999
_reflns_number_total                    3920
_reflns_number_gt                       2523
_reflns_threshold_expression            >2sigma(I)
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
 
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
 
_computing_data_collection              'APEX2 (Bruker,2004)'
_computing_cell_refinement              'APEX2 (Bruker,2004)'
_computing_data_reduction               'APEX2 (Bruker,2004)'
_computing_structure_solution           'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 1999)'
 
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The isopropyl groups show high thermal motion. A difference Fourier map
 in this region gave no evidence for disorder.
;
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1016P)²+0.4246P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
_refine_ls_hydrogen_treatment           noref
_refine_ls_extinction_method            SHELXL
_refine_ls_extinction_expression
                                    Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef              0.0059(19)
_refine_ls_number_reflns                3920
_refine_ls_number_parameters            218
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.0998
_refine_ls_R_factor_gt                  0.0631
_refine_ls_wR_factor_ref                0.2041
_refine_ls_wR_factor_gt                 0.1806
_refine_ls_goodness_of_fit_ref          1.086
_refine_ls_restrained_S_all             1.086
_refine_ls_shift/su_max                 0.004
_refine_ls_shift/su_mean                0.001
_refine_diff_density_max                0.444
_refine_diff_density_min                -0.323
_refine_diff_density_rms                0.043
 
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
 
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
loop_
    _atom_site_label
    _atom_site_type_symbol
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_disorder_assembly
    _atom_site_disorder_group
C1 C 0.13145(19) 0.0048(3) 0.46025(15) 0.0574(7) Uani 1 1 d . . .
H1A H 0.2099 -0.014 0.473 0.069 Uiso 1 1 calc R . .
H1B H 0.1137 -0.0216 0.5088 0.069 Uiso 1 1 calc R . .
C2 C 0.11058(19) 0.1600(3) 0.44460(16) 0.0569(6) Uani 1 1 d . . .
H2A H 0.176 0.2108 0.4793 0.068 Uiso 1 1 calc R . .
H2B H 0.0991 0.18 0.3864 0.068 Uiso 1 1 calc R . .
C3 C 0.0474(2) -0.2225(3) 0.41254(16) 0.0598(7) Uani 1 1 d . . .
H3A H 0.1155 -0.2555 0.4552 0.072 Uiso 1 1 calc R . .
H3B H 0.031 -0.2832 0.3642 0.072 Uiso 1 1 calc R . .
C4 C -0.0461(2) -0.2323(3) 0.44584(14) 0.0544(6) Uani 1 1 d . . .
H4A H -0.1026 -0.1646 0.4166 0.065 Uiso 1 1 calc R . .
H4B H -0.0795 -0.324 0.4326 0.065 Uiso 1 1 calc R . .
C10 C 0.1140(2) -0.0802(3) 0.32260(17) 0.0694(8) Uani 1 1 d . . .
H10A H 0.1767 -0.1438 0.3383 0.083 Uiso 1 1 calc R . .
H10B H 0.142 0.0126 0.3192 0.083 Uiso 1 1 calc R . .
C11 C 0.0330(3) -0.1207(3) 0.23772(17) 0.0753(9) Uani 1 1 d . . .
H11A H 0.0702 -0.1194 0.1974 0.09 Uiso 1 1 calc R . .
H11B H 0.0067 -0.2148 0.2401 0.09 Uiso 1 1 calc R . .
C12 C -0.1564(2) -0.0712(3) 0.21908(15) 0.0553(6) Uani 1 1 d . . .
C13 C -0.3453(2) 0.0056(3) 0.19695(19) 0.0745(8) Uani 1 1 d . . .
H13 H -0.3682 -0.0898 0.1781 0.089 Uiso 1 1 calc R . .
C14 C -0.4243(3) 0.1040(7) 0.1352(4) 0.195(3) Uani 1 1 d . . .
H14A H -0.4203 0.0901 0.0807 0.292 Uiso 1 1 calc R . .
H14B H -0.4041 0.1983 0.1528 0.292 Uiso 1 1 calc R . .
H14C H -0.4989 0.0864 0.1327 0.292 Uiso 1 1 calc R . .
C15 C -0.3485(3) 0.0215(4) 0.2832(2) 0.1029(12) Uani 1 1 d . . .
H15A H -0.2985 -0.0444 0.3203 0.154 Uiso 1 1 calc R . .
H15B H -0.4228 0.0047 0.2816 0.154 Uiso 1 1 calc R . .
H15C H -0.3263 0.1143 0.3031 0.154 Uiso 1 1 calc R . .
C20 C -0.0315(2) 0.3379(2) 0.41701(14) 0.0533(6) Uani 1 1 d . . .
H20A H 0.029 0.3987 0.4177 0.064 Uiso 1 1 calc R . .
H20B H -0.0756 0.3861 0.4442 0.064 Uiso 1 1 calc R . .
C21 C -0.1032(2) 0.3043(3) 0.32748(15) 0.0602(7) Uani 1 1 d . . .
H21A H -0.0616 0.2484 0.3015 0.072 Uiso 1 1 calc R . .
H21B H -0.1684 0.2521 0.326 0.072 Uiso 1 1 calc R . .
C22 C -0.1804(2) 0.4230(3) 0.19828(15) 0.0510(6) Uani 1 1 d . . .
C23 C -0.2454(3) 0.5638(3) 0.07049(16) 0.0761(9) Uani 1 1 d . . .
H23 H -0.2241 0.4815 0.0458 0.091 Uiso 1 1 calc R . .
C24 C -0.1940(5) 0.6896(5) 0.0471(2) 0.145(2) Uani 1 1 d . . .
H24A H -0.1145 0.6804 0.0689 0.218 Uiso 1 1 calc R . .
H24B H -0.215 0.7714 0.0702 0.218 Uiso 1 1 calc R . .
H24C H -0.2198 0.6976 -0.0129 0.218 Uiso 1 1 calc R . .
C25 C -0.3647(4) 0.5739(9) 0.0382(3) 0.227(4) Uani 1 1 d . . .
H25A H -0.3958 0.4912 0.0526 0.341 Uiso 1 1 calc R . .
H25B H -0.3908 0.5836 -0.0217 0.341 Uiso 1 1 calc R . .
H25C H -0.387 0.6536 0.0622 0.341 Uiso 1 1 calc R . .
N1 N 0.06545(16) -0.0814(2) 0.38823(12) 0.0526(5) Uani 1 1 d . . .
N2 N 0.01392(15) 0.2090(2) 0.46284(11) 0.0482(5) Uani 1 1 d . . .
N10 N -0.23386(17) 0.0272(2) 0.19545(14) 0.0604(6) Uani 1 1 d . . .
H10 H -0.2179 0.1061 0.1787 0.073 Uiso 1 1 calc R . .
N20 N -0.2030(2) 0.5472(2) 0.16204(13) 0.0685(7) Uani 1 1 d . . .
H20 H -0.1926 0.6202 0.1931 0.082 Uiso 1 1 calc R . .
O10 O -0.06081(15) -0.0264(2) 0.21060(11) 0.0637(5) Uani 1 1 d . . .
O11 O -0.16920(18) -0.18753(19) 0.24282(12) 0.0745(6) Uani 1 1 d . . .
O21 O -0.13621(14) 0.43377(16) 0.28313(10) 0.0544(5) Uani 1 1 d . . .
O22 O -0.19465(17) 0.31270(18) 0.16144(11) 0.0714(6) Uani 1 1 d . . .
 
 
 
#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_distance
    _geom_bond_site_symmetry_2
    _geom_bond_publ_flag
C1 N1 1.472(3) . ?
C1 C2 1.520(4) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C2 N2 1.464(3) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 N1 1.459(3) . ?
C3 C4 1.507(4) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 N2 1.480(3) 3_556 ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C10 N1 1.466(3) . ?
C10 C11 1.501(4) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 O10 1.445(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 O11 1.219(3) . ?
C12 N10 1.326(3) . ?
C12 O10 1.360(3) . ?
C13 N10 1.459(3) . ?
C13 C15 1.496(4) . ?
C13 C14 1.506(5) . ?
C13 H13 0.98 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C20 N2 1.468(3) . ?
C20 C21 1.510(3) . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C21 O21 1.438(3) . ?
C21 H21A 0.97 . ?
C21 H21B 0.97 . ?
C22 O22 1.212(3) . ?
C22 N20 1.326(3) . ?
C22 O21 1.357(3) . ?
C23 C25 1.435(6) . ?
C23 N20 1.468(3) . ?
C23 C24 1.498(5) . ?
C23 H23 0.98 . ?
C24 H24A 0.96 . ?
C24 H24B 0.96 . ?
C24 H24C 0.96 . ?
C25 H25A 0.96 . ?
C25 H25B 0.96 . ?
C25 H25C 0.96 . ?
N2 C4 1.480(3) 3_556 ?
N10 H10 0.86 . ?
N20 H20 0.86 . ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
N1 C1 C2 113.03(19) . . ?
N1 C1 H1A 109 . . ?
C2 C1 H1A 109 . . ?
N1 C1 H1B 109 . . ?
C2 C1 H1B 109 . . ?
H1A C1 H1B 107.8 . . ?
N2 C2 C1 112.80(19) . . ?
N2 C2 H2A 109 . . ?
C1 C2 H2A 109 . . ?
N2 C2 H2B 109 . . ?
C1 C2 H2B 109 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C4 113.3(2) . . ?
N1 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
N1 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
N2 C4 C3 115.42(19) 3_556 . ?
N2 C4 H4A 108.4 3_556 . ?
C3 C4 H4A 108.4 . . ?
N2 C4 H4B 108.4 3_556 . ?
C3 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
N1 C10 C11 113.4(2) . . ?
N1 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
O10 C11 C10 110.9(2) . . ?
O10 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
O10 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108 . . ?
O11 C12 N10 125.3(3) . . ?
O11 C12 O10 124.1(3) . . ?
N10 C12 O10 110.6(2) . . ?
N10 C13 C15 112.2(2) . . ?
N10 C13 C14 108.6(3) . . ?
C15 C13 C14 112.0(4) . . ?
N10 C13 H13 107.9 . . ?
C15 C13 H13 107.9 . . ?
C14 C13 H13 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C20 C21 109.96(19) . . ?
N2 C20 H20A 109.7 . . ?
C21 C20 H20A 109.7 . . ?
N2 C20 H20B 109.7 . . ?
C21 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
O21 C21 C20 107.85(19) . . ?
O21 C21 H21A 110.1 . . ?
C20 C21 H21A 110.1 . . ?
O21 C21 H21B 110.1 . . ?
C20 C21 H21B 110.1 . . ?
H21A C21 H21B 108.5 . . ?
O22 C22 N20 125.2(2) . . ?
O22 C22 O21 123.2(2) . . ?
N20 C22 O21 111.6(2) . . ?
C25 C23 N20 110.7(3) . . ?
C25 C23 C24 110.9(4) . . ?
N20 C23 C24 109.9(3) . . ?
C25 C23 H23 108.4 . . ?
N20 C23 H23 108.4 . . ?
C24 C23 H23 108.4 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C3 N1 C10 112.3(2) . . ?
C3 N1 C1 112.76(19) . . ?
C10 N1 C1 110.9(2) . . ?
C2 N2 C20 111.32(18) . . ?
C2 N2 C4 109.59(17) . 3_556 ?
C20 N2 C4 109.95(19) . 3_556 ?
C12 N10 C13 122.0(2) . . ?
C12 N10 H10 119 . . ?
C13 N10 H10 119 . . ?
C22 N20 C23 122.0(2) . . ?
C22 N20 H20 119 . . ?
C23 N20 H20 119 . . ?
C12 O10 C11 116.9(2) . . ?
C22 O21 C21 115.34(18) . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
N1 C1 C2 N2 85.1(3) . . . . ?
N1 C3 C4 N2 -88.4(3) . . . 3_556 ?
N1 C10 C11 O10 60.0(3) . . . . ?
N2 C20 C21 O21 -174.18(19) . . . . ?
C4 C3 N1 C10 -152.8(2) . . . . ?
C4 C3 N1 C1 80.9(2) . . . . ?
C11 C10 N1 C3 73.3(3) . . . . ?
C11 C10 N1 C1 -159.4(2) . . . . ?
C2 C1 N1 C3 -155.4(2) . . . . ?
C2 C1 N1 C10 77.5(2) . . . . ?
C1 C2 N2 C20 -156.87(19) . . . . ?
C1 C2 N2 C4 81.3(2) . . . 3_556 ?
C21 C20 N2 C2 80.1(2) . . . . ?
C21 C20 N2 C4 -158.3(2) . . . 3_556 ?
O11 C12 N10 C13 1.1(4) . . . . ?
O10 C12 N10 C13 179.0(2) . . . . ?
C15 C13 N10 C12 79.4(4) . . . . ?
C14 C13 N10 C12 -156.2(4) . . . . ?
O22 C22 N20 C23 -2.3(5) . . . . ?
O21 C22 N20 C23 176.4(2) . . . . ?
C25 C23 N20 C22 95.6(5) . . . . ?
C24 C23 N20 C22 -141.5(4) . . . . ?
O11 C12 O10 C11 -4.8(3) . . . . ?
N10 C12 O10 C11 177.2(2) . . . . ?
C10 C11 O10 C12 -101.0(3) . . . . ?
O22 C22 O21 C21 2.1(4) . . . . ?
N20 C22 O21 C21 -176.6(2) . . . . ?
C20 C21 O21 C22 166.2(2) . . . . ?
 
