#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:24:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179577 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/42/4504266.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4504266
loop_
_publ_author_name
'Cheney, Miranda L.'
'McManus, Gregory J.'
'Perman, Jason A.'
'Wang, Zhenqiang'
'Zaworotko, Michael J.'
_publ_section_title
;
 The Role of Cocrystals in Solid-State Synthesis: 
 Cocrystal-Controlled Solid-State Synthesis of Imides
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              616
_journal_paper_doi               10.1021/cg0701729
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C42 H24 N5 O8'
_chemical_formula_weight         726.66
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.287(4)
_cell_angle_beta                 102.202(4)
_cell_angle_gamma                96.564(4)
_cell_formula_units_Z            1
_cell_length_a                   7.1569(14)
_cell_length_b                   8.1962(17)
_cell_length_c                   15.448(3)
_cell_measurement_reflns_used    1019
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.68
_cell_measurement_theta_min      2.54
_cell_volume                     866.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.1075
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3645
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.345
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             375
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0869
_refine_ls_shift/su_max          4.254
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0718P)²+2.3232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2019
_refine_ls_wR_factor_ref         0.2323
_reflns_number_gt                1846
_reflns_number_total             2852
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0701729si20070219_052917.cif
_cod_data_source_block           mc4542
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4504266
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.0010(5) -0.1863(4) 0.9407(2) 0.0270(9) Uani 1 1 d .
H1 H 0.0960 -0.2083 0.9770 0.041 Uiso 1 1 calc R
O2 O 0.2289(5) -0.0943(4) 0.8726(2) 0.0299(9) Uani 1 1 d .
O3 O -0.0116(5) 0.4480(4) 0.7649(2) 0.0261(8) Uani 1 1 d .
O4 O -0.2167(5) 0.0174(4) 0.5290(2) 0.0291(9) Uani 1 1 d .
N1 N -0.1153(6) 0.2332(5) 0.6469(3) 0.0211(9) Uani 1 1 d .
C1 C -0.0913(7) -0.0377(5) 0.8225(3) 0.0202(11) Uani 1 1 d .
C2 C -0.0366(7) 0.0591(5) 0.7624(3) 0.0216(11) Uani 1 1 d .
H2 H 0.0950 0.0787 0.7592 0.026 Uiso 1 1 calc R
C3 C -0.1753(7) 0.1267(5) 0.7072(3) 0.0206(11) Uani 1 1 d .
C4 C -0.3678(7) 0.0989(6) 0.7107(3) 0.0251(12) Uani 1 1 d .
H4 H -0.4624 0.1446 0.6724 0.030 Uiso 1 1 calc R
C5 C -0.4200(8) 0.0026(6) 0.7714(3) 0.0257(12) Uani 1 1 d .
H5 H -0.5517 -0.0179 0.7743 0.031 Uiso 1 1 calc R
C6 C -0.2820(7) -0.0638(5) 0.8277(3) 0.0227(11) Uani 1 1 d .
H6 H -0.3190 -0.1272 0.8699 0.027 Uiso 1 1 calc R
C7 C 0.0621(8) -0.1083(5) 0.8819(3) 0.0222(11) Uani 1 1 d .
C8 C -0.0365(7) 0.3995(6) 0.6843(3) 0.0199(11) Uani 1 1 d .
C9 C 0.0140(6) 0.5095(5) 0.6222(3) 0.0174(10) Uani 1 1 d .
C10 C 0.0909(7) 0.6743(6) 0.6553(3) 0.0215(11) Uani 1 1 d .
H10 H 0.1149 0.7158 0.7179 0.026 Uiso 1 1 calc R
C11 C -0.1336(7) 0.2195(5) 0.4036(3) 0.0199(11) Uani 1 1 d .
H11 H -0.1856 0.1058 0.3805 0.024 Uiso 1 1 calc R
C12 C -0.1014(7) 0.2769(5) 0.4940(3) 0.0197(11) Uani 1 1 d .
C13 C -0.1484(7) 0.1631(6) 0.5556(3) 0.0216(11) Uani 1 1 d .
C14 C -0.0215(7) 0.4464(5) 0.5292(3) 0.0173(10) Uani 1 1 d .
N21 N 0.7236(6) 0.3044(5) 0.9642(3) 0.0233(10) Uani 1 1 d .
C21 C 0.7665(8) 0.4116(6) 0.9120(3) 0.0242(12) Uani 1 1 d .
H21 H 0.8984 0.4421 0.9116 0.029 Uiso 1 1 calc R
C22 C 0.6288(8) 0.4804(6) 0.8585(3) 0.0303(13) Uani 1 1 d .
H22 H 0.6649 0.5551 0.8211 0.036 Uiso 1 1 calc R
C23 C 0.4364(8) 0.4388(6) 0.8600(4) 0.0353(14) Uani 1 1 d .
H23 H 0.3386 0.4873 0.8253 0.042 Uiso 1 1 calc R
C24 C 0.3896(8) 0.3249(6) 0.9131(4) 0.0328(13) Uani 1 1 d .
H24 H 0.2587 0.2914 0.9141 0.039 Uiso 1 1 calc R
C25 C 0.5368(8) 0.2610(6) 0.9644(4) 0.0307(13) Uani 1 1 d .
H25 H 0.5049 0.1838 1.0013 0.037 Uiso 1 1 calc R
N31 N 0.4337(9) 0.3585(7) 0.5266(5) 0.0098(15) Uani 0.50 1 d P
C31 C 0.5071(8) 0.4914(9) 0.5896(4) 0.0437(16) Uani 1 1 d .
C32 C 0.4257(8) 0.3596(8) 0.4389(5) 0.055(2) Uani 1 1 d .
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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C8 N1 C13 125.2(4) . .
C8 N1 C3 117.3(4) . .
C13 N1 C3 117.4(4) . .
C6 C1 C2 119.9(5) . .
C6 C1 C7 121.6(4) . .
C2 C1 C7 118.5(4) . .
C3 C2 C1 119.7(5) . .
C4 C3 C2 120.9(4) . .
C4 C3 N1 119.8(4) . .
C2 C3 N1 119.2(4) . .
C3 C4 C5 118.7(5) . .
C6 C5 C4 120.8(5) . .
C1 C6 C5 119.9(4) . .
O2 C7 O1 124.5(5) . .
O2 C7 C1 121.1(4) . .
O1 C7 C1 114.4(4) . .
O3 C8 N1 120.1(4) . .
O3 C8 C9 122.6(4) . .
N1 C8 C9 117.3(4) . .
C10 C9 C14 120.4(4) . .
C10 C9 C8 119.7(4) . .
C14 C9 C8 119.9(4) . .
C9 C10 C11 119.9(4) . 2_566
C12 C11 C10 121.0(4) . 2_566
C11 C12 C14 119.7(4) . .
C11 C12 C13 120.4(4) . .
C14 C12 C13 119.8(4) . .
O4 C13 N1 120.8(4) . .
O4 C13 C12 122.5(4) . .
N1 C13 C12 116.7(4) . .
C14 C14 C9 119.2(5) 2_566 .
C14 C14 C12 119.6(5) 2_566 .
C9 C14 C12 121.1(4) . .
C21 N21 C25 118.4(5) . .
N21 C21 C22 123.0(5) . .
C21 C22 C23 118.8(5) . .
C22 C23 C24 118.7(5) . .
C25 C24 C23 118.8(5) . .
N21 C25 C24 122.3(5) . .
C31 N31 C32 122.5(6) . .
N31 C31 C32 117.3(6) . 2_666
N31 C32 C31 120.1(6) . 2_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.303(5) .
O2 C7 1.227(6) .
O3 C8 1.221(5) .
O4 C13 1.214(5) .
N1 C8 1.403(6) .
N1 C13 1.404(6) .
N1 C3 1.459(5) .
C1 C6 1.379(7) .
C1 C2 1.393(6) .
C1 C7 1.501(7) .
C2 C3 1.387(6) .
C3 C4 1.384(7) .
C4 C5 1.392(6) .
C5 C6 1.387(7) .
C8 C9 1.477(6) .
C9 C10 1.378(6) .
C9 C14 1.414(6) .
C10 C11 1.402(6) 2_566
C11 C12 1.369(6) .
C11 C10 1.402(6) 2_566
C12 C14 1.422(6) .
C12 C13 1.485(6) .
C14 C14 1.402(8) 2_566
N21 C21 1.329(6) .
N21 C25 1.345(6) .
C21 C22 1.374(7) .
C22 C23 1.386(8) .
C23 C24 1.387(8) .
C24 C25 1.380(8) .
N31 C31 1.326(9) .
N31 C32 1.344(10) .
C31 C32 1.424(9) 2_666
C32 C31 1.424(9) 2_666
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_4
C6 C1 C2 C3 -0.9(7) . .
C7 C1 C2 C3 -179.6(4) . .
C1 C2 C3 C4 -0.3(7) . .
C1 C2 C3 N1 177.7(4) . .
C8 N1 C3 C4 98.2(5) . .
C13 N1 C3 C4 -79.2(6) . .
C8 N1 C3 C2 -79.7(5) . .
C13 N1 C3 C2 102.8(5) . .
C2 C3 C4 C5 0.6(7) . .
N1 C3 C4 C5 -177.3(4) . .
C3 C4 C5 C6 0.3(7) . .
C2 C1 C6 C5 1.8(7) . .
C7 C1 C6 C5 -179.6(4) . .
C4 C5 C6 C1 -1.5(7) . .
C6 C1 C7 O2 174.9(4) . .
C2 C1 C7 O2 -6.4(7) . .
C6 C1 C7 O1 -3.7(6) . .
C2 C1 C7 O1 175.0(4) . .
C13 N1 C8 O3 -179.2(4) . .
C3 N1 C8 O3 3.5(7) . .
C13 N1 C8 C9 0.6(7) . .
C3 N1 C8 C9 -176.7(4) . .
O3 C8 C9 C10 -0.5(7) . .
N1 C8 C9 C10 179.6(4) . .
O3 C8 C9 C14 -178.9(4) . .
N1 C8 C9 C14 1.2(6) . .
C14 C9 C10 C11 0.3(7) . 2_566
C8 C9 C10 C11 -178.1(4) . 2_566
C10 C11 C12 C14 -0.7(7) 2_566 .
C10 C11 C12 C13 179.7(4) 2_566 .
C8 N1 C13 O4 179.7(5) . .
C3 N1 C13 O4 -3.0(7) . .
C8 N1 C13 C12 -2.1(7) . .
C3 N1 C13 C12 175.1(4) . .
C11 C12 C13 O4 -0.3(7) . .
C14 C12 C13 O4 -180.0(5) . .
C11 C12 C13 N1 -178.5(4) . .
C14 C12 C13 N1 1.9(6) . .
C10 C9 C14 C14 -0.4(8) . 2_566
C8 C9 C14 C14 178.0(5) . 2_566
C10 C9 C14 C12 -179.8(4) . .
C8 C9 C14 C12 -1.4(7) . .
C11 C12 C14 C14 0.8(8) . 2_566
C13 C12 C14 C14 -179.6(5) . 2_566
C11 C12 C14 C9 -179.8(4) . .
C13 C12 C14 C9 -0.2(7) . .
C25 N21 C21 C22 0.2(7) . .
N21 C21 C22 C23 1.2(8) . .
C21 C22 C23 C24 -2.2(8) . .
C22 C23 C24 C25 1.9(8) . .
C21 N21 C25 C24 -0.5(7) . .
C23 C24 C25 N21 -0.5(8) . .
C32 N31 C31 C32 1.6(10) . 2_666
C31 N31 C32 C31 -1.7(11) . 2_666
