#------------------------------------------------------------------------------
#$Date: 2017-05-06 00:36:28 +0300 (Sat, 06 May 2017) $
#$Revision: 196294 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/99/7119946.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_7119946
loop_
_publ_author_name
'Khorasani, S.'
'Fernandes, M. A.'
_publ_section_title
;
 A synthetic co-crystal prepared by cooperative
 single-crystal-to-single-crystal solid-state Diels-Alder reaction.
;
_journal_issue                   36
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4969
_journal_page_last               4972
_journal_paper_doi               10.1039/c6cc07628a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety
;
C16 H14 N2 O4 S2, 2(C14 H9 Br)
;
_chemical_formula_sum            'C44 H32 Br2 N2 O4 S2'
_chemical_formula_weight         876.65
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-06 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                93.2960(10)
_cell_angle_beta                 109.1360(10)
_cell_angle_gamma                92.3010(10)
_cell_formula_units_Z            1
_cell_length_a                   8.6797(2)
_cell_length_b                   9.6861(2)
_cell_length_c                   11.3175(2)
_cell_measurement_reflns_used    8008
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.49
_cell_volume                     895.67(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23410
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_min         1.910
_exptl_absorpt_coefficient_mu    2.429
_exptl_absorpt_correction_T_max  0.9087
_exptl_absorpt_correction_T_min  0.6300
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Face indexed absorption corrections carried out with XPREP
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.209
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0490P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3217
_reflns_number_total             4329
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc07628a2.cif
_cod_data_source_block           D4Br_0h_CT
_cod_depositor_comments
'Adding full bibliography for 7119945--7119961.cif.'
_cod_database_code               7119946
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.510
_shelx_estimated_absorpt_t_max   0.931
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.2318(3) 0.6558(2) 0.34399(19) 0.0232(4) Uani 1 1 d . .
C2 C 0.3596(2) 0.5658(2) 0.41817(19) 0.0214(4) Uani 1 1 d . .
C3 C 0.5007(2) 0.6425(2) 0.46562(18) 0.0213(4) Uani 1 1 d . .
C4 C 0.4738(3) 0.7849(2) 0.42174(19) 0.0218(4) Uani 1 1 d . .
C5 C 0.2280(3) 0.9133(2) 0.3131(2) 0.0260(5) Uani 1 1 d . .
H5 H 0.3121 0.9927 0.3361 0.031 Uiso 1 1 calc R U
C6 C 0.0873(3) 0.9516(3) 0.3603(2) 0.0338(5) Uani 1 1 d . .
H6A H 0.1201 1.0190 0.4346 0.041 Uiso 1 1 calc R U
H6B H 0.0222 0.8708 0.3726 0.041 Uiso 1 1 calc R U
C7 C 0.0103(3) 1.0168(3) 0.2347(2) 0.0360(6) Uani 1 1 d . .
H7A H 0.0384 1.1173 0.2379 0.043 Uiso 1 1 calc R U
H7B H -0.1090 0.9956 0.1964 0.043 Uiso 1 1 calc R U
C8 C 0.1142(3) 0.9245(3) 0.1786(2) 0.0344(6) Uani 1 1 d . .
H8A H 0.0571 0.8355 0.1362 0.041 Uiso 1 1 calc R U
H8B H 0.1657 0.9729 0.1251 0.041 Uiso 1 1 calc R U
N1 N 0.3094(2) 0.78609(18) 0.35134(16) 0.0238(4) Uani 1 1 d . .
O1 O 0.08999(18) 0.62178(16) 0.28935(15) 0.0310(4) Uani 1 1 d . .
O2 O 0.57524(18) 0.87941(15) 0.44267(14) 0.0282(3) Uani 1 1 d . .
S1 S 0.30700(6) 0.39384(5) 0.43427(5) 0.02222(12) Uani 1 1 d . .
C9 C 0.3934(3) 0.4155(2) 0.13781(19) 0.0272(5) Uani 1 1 d . .
C10 C 0.3889(3) 0.5516(2) 0.10228(19) 0.0264(5) Uani 1 1 d . .
C11 C 0.2499(3) 0.6055(3) 0.0138(2) 0.0326(5) Uani 1 1 d . .
H11 H 0.1529 0.5477 -0.0237 0.039 Uiso 1 1 calc R U
C12 C 0.2559(3) 0.7377(3) -0.0167(2) 0.0385(6) Uani 1 1 d . .
H12 H 0.1634 0.7709 -0.0772 0.046 Uiso 1 1 calc R U
C13 C 0.3955(3) 0.8278(3) 0.0388(2) 0.0398(6) Uani 1 1 d . .
H13 H 0.3950 0.9212 0.0174 0.048 Uiso 1 1 calc R U
C14 C 0.5307(3) 0.7821(2) 0.1226(2) 0.0331(5) Uani 1 1 d . .
H14 H 0.6246 0.8436 0.1593 0.040 Uiso 1 1 calc R U
C15 C 0.5336(3) 0.6417(2) 0.15635(19) 0.0256(5) Uani 1 1 d . .
C16 C 0.6731(3) 0.5914(2) 0.2374(2) 0.0274(5) Uani 1 1 d . .
H16 H 0.7682 0.6519 0.2724 0.033 Uiso 1 1 calc R U
C17 C 0.6777(3) 0.4543(2) 0.26917(19) 0.0245(5) Uani 1 1 d . .
C18 C 0.8233(3) 0.4016(2) 0.3482(2) 0.0297(5) Uani 1 1 d . .
H18 H 0.9199 0.4609 0.3799 0.036 Uiso 1 1 calc R U
C19 C 0.8272(3) 0.2684(3) 0.3791(2) 0.0334(5) Uani 1 1 d . .
H19 H 0.9260 0.2353 0.4319 0.040 Uiso 1 1 calc R U
C20 C 0.6840(3) 0.1779(3) 0.3330(2) 0.0351(6) Uani 1 1 d . .
H20 H 0.6874 0.0850 0.3559 0.042 Uiso 1 1 calc R U
C21 C 0.5425(3) 0.2231(2) 0.2564(2) 0.0309(5) Uani 1 1 d . .
H21 H 0.4477 0.1614 0.2267 0.037 Uiso 1 1 calc R U
C22 C 0.5338(3) 0.3626(2) 0.2198(2) 0.0255(5) Uani 1 1 d . .
Br1 Br 0.20204(3) 0.29557(3) 0.06931(2) 0.04024(10) 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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_3
O1 C1 N1 127.02(19) .
O1 C1 C2 126.6(2) .
N1 C1 C2 106.37(17) .
C3 C2 C1 108.31(19) .
C3 C2 S1 131.68(17) .
C1 C2 S1 119.96(15) .
C2 C3 C4 108.39(18) .
C2 C3 S1 132.34(17) 2_666
C4 C3 S1 119.24(15) 2_666
O2 C4 N1 126.82(19) .
O2 C4 C3 126.54(19) .
N1 C4 C3 106.64(18) .
N1 C5 C8 121.19(18) .
N1 C5 C6 118.86(19) .
C8 C5 C6 88.86(17) .
N1 C5 H5 108.7 .
C8 C5 H5 108.7 .
C6 C5 H5 108.7 .
C5 C6 C7 87.41(17) .
C5 C6 H6A 114.1 .
C7 C6 H6A 114.1 .
C5 C6 H6B 114.1 .
C7 C6 H6B 114.1 .
H6A C6 H6B 111.3 .
C6 C7 C8 88.05(17) .
C6 C7 H7A 114.0 .
C8 C7 H7A 114.0 .
C6 C7 H7B 114.0 .
C8 C7 H7B 114.0 .
H7A C7 H7B 111.2 .
C5 C8 C7 87.33(17) .
C5 C8 H8A 114.1 .
C7 C8 H8A 114.1 .
C5 C8 H8B 114.1 .
C7 C8 H8B 114.1 .
H8A C8 H8B 111.3 .
C4 N1 C1 110.25(17) .
C4 N1 C5 123.10(18) .
C1 N1 C5 125.65(18) .
C2 S1 C3 95.97(10) 2_666
C10 C9 C22 123.1(2) .
C10 C9 Br1 118.47(16) .
C22 C9 Br1 118.46(17) .
C9 C10 C11 124.0(2) .
C9 C10 C15 117.9(2) .
C11 C10 C15 118.2(2) .
C12 C11 C10 120.4(2) .
C12 C11 H11 119.8 .
C10 C11 H11 119.8 .
C11 C12 C13 121.7(2) .
C11 C12 H12 119.1 .
C13 C12 H12 119.1 .
C14 C13 C12 120.3(2) .
C14 C13 H13 119.8 .
C12 C13 H13 119.8 .
C13 C14 C15 120.6(2) .
C13 C14 H14 119.7 .
C15 C14 H14 119.7 .
C16 C15 C14 121.4(2) .
C16 C15 C10 119.9(2) .
C14 C15 C10 118.7(2) .
C15 C16 C17 121.8(2) .
C15 C16 H16 119.1 .
C17 C16 H16 119.1 .
C16 C17 C18 121.6(2) .
C16 C17 C22 119.8(2) .
C18 C17 C22 118.6(2) .
C19 C18 C17 121.4(2) .
C19 C18 H18 119.3 .
C17 C18 H18 119.3 .
C18 C19 C20 120.2(2) .
C18 C19 H19 119.9 .
C20 C19 H19 119.9 .
C21 C20 C19 120.6(2) .
C21 C20 H20 119.7 .
C19 C20 H20 119.7 .
C20 C21 C22 121.0(2) .
C20 C21 H21 119.5 .
C22 C21 H21 119.5 .
C9 C22 C21 124.2(2) .
C9 C22 C17 117.6(2) .
C21 C22 C17 118.2(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.204(3) .
C1 N1 1.391(3) .
C1 C2 1.499(3) .
C2 C3 1.338(3) .
C2 S1 1.745(2) .
C3 C4 1.494(3) .
C3 S1 1.745(2) 2_666
C4 O2 1.201(3) .
C4 N1 1.389(3) .
C5 N1 1.461(3) .
C5 C8 1.532(3) .
C5 C6 1.534(3) .
C5 H5 1.0000 .
C6 C7 1.542(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.546(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
S1 C3 1.745(2) 2_666
C9 C10 1.398(3) .
C9 C22 1.405(3) .
C9 Br1 1.899(2) .
C10 C11 1.431(3) .
C10 C15 1.435(3) .
C11 C12 1.349(4) .
C11 H11 0.9500 .
C12 C13 1.406(4) .
C12 H12 0.9500 .
C13 C14 1.354(4) .
C13 H13 0.9500 .
C14 C15 1.432(3) .
C14 H14 0.9500 .
C15 C16 1.384(3) .
C16 C17 1.394(3) .
C16 H16 0.9500 .
C17 C18 1.422(3) .
C17 C22 1.434(3) .
C18 C19 1.355(3) .
C18 H18 0.9500 .
C19 C20 1.421(4) .
C19 H19 0.9500 .
C20 C21 1.356(3) .
C20 H20 0.9500 .
C21 C22 1.434(3) .
C21 H21 0.9500 .
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
O1 C1 C2 C3 -179.1(2) . .
N1 C1 C2 C3 0.7(2) . .
O1 C1 C2 S1 -1.4(3) . .
N1 C1 C2 S1 178.39(14) . .
C1 C2 C3 C4 -1.8(2) . .
S1 C2 C3 C4 -179.08(16) . .
C1 C2 C3 S1 176.27(16) . 2_666
S1 C2 C3 S1 -1.0(4) . 2_666
C2 C3 C4 O2 -177.2(2) . .
S1 C3 C4 O2 4.4(3) 2_666 .
C2 C3 C4 N1 2.2(2) . .
S1 C3 C4 N1 -176.10(14) 2_666 .
N1 C5 C6 C7 -147.2(2) . .
C8 C5 C6 C7 -21.72(18) . .
C5 C6 C7 C8 21.53(18) . .
N1 C5 C8 C7 145.2(2) . .
C6 C5 C8 C7 21.67(18) . .
C6 C7 C8 C5 -21.55(19) . .
O2 C4 N1 C1 177.7(2) . .
C3 C4 N1 C1 -1.8(2) . .
O2 C4 N1 C5 -13.2(3) . .
C3 C4 N1 C5 167.34(18) . .
O1 C1 N1 C4 -179.4(2) . .
C2 C1 N1 C4 0.8(2) . .
O1 C1 N1 C5 11.8(3) . .
C2 C1 N1 C5 -168.03(18) . .
C8 C5 N1 C4 134.3(2) . .
C6 C5 N1 C4 -117.8(2) . .
C8 C5 N1 C1 -58.3(3) . .
C6 C5 N1 C1 49.6(3) . .
C3 C2 S1 C3 0.8(3) . 2_666
C1 C2 S1 C3 -176.28(16) . 2_666
C22 C9 C10 C11 176.5(2) . .
Br1 C9 C10 C11 -2.1(3) . .
C22 C9 C10 C15 -2.3(3) . .
Br1 C9 C10 C15 179.02(15) . .
C9 C10 C11 C12 -179.2(2) . .
C15 C10 C11 C12 -0.4(3) . .
C10 C11 C12 C13 -1.6(4) . .
C11 C12 C13 C14 1.9(4) . .
C12 C13 C14 C15 -0.2(4) . .
C13 C14 C15 C16 177.0(2) . .
C13 C14 C15 C10 -1.7(3) . .
C9 C10 C15 C16 2.2(3) . .
C11 C10 C15 C16 -176.73(19) . .
C9 C10 C15 C14 -179.12(19) . .
C11 C10 C15 C14 2.0(3) . .
C14 C15 C16 C17 -178.9(2) . .
C10 C15 C16 C17 -0.2(3) . .
C15 C16 C17 C18 177.2(2) . .
C15 C16 C17 C22 -1.6(3) . .
C16 C17 C18 C19 179.8(2) . .
C22 C17 C18 C19 -1.3(3) . .
C17 C18 C19 C20 -0.2(3) . .
C18 C19 C20 C21 0.7(3) . .
C19 C20 C21 C22 0.2(3) . .
C10 C9 C22 C21 -179.1(2) . .
Br1 C9 C22 C21 -0.4(3) . .
C10 C9 C22 C17 0.5(3) . .
Br1 C9 C22 C17 179.15(15) . .
C20 C21 C22 C9 177.9(2) . .
C20 C21 C22 C17 -1.7(3) . .
C16 C17 C22 C9 1.5(3) . .
C18 C17 C22 C9 -177.39(18) . .
C16 C17 C22 C21 -178.86(19) . .
C18 C17 C22 C21 2.2(3) . .
