#------------------------------------------------------------------------------
#$Date: 2021-07-10 07:41:29 +0300 (Sat, 10 Jul 2021) $
#$Revision: 267457 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243866.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243866
loop_
_publ_author_name
'Alikhanova, Aygun I.'
'Atioğlu, Zeliha'
'Akkurt, Mehmet'
'Mlowe, Sixberth'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (3aR,4S,7S,7aS)-4,5,6,7,8,8-hexachloro-2-{6-[(3aR,4R,7R,7aS)-4,5,6,7,8,8-hexachloro-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl]hexyl}-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione
;
_journal_coeditor_code           VM2251
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              775
_journal_page_last               779
_journal_paper_doi               10.1107/S2056989021006952
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C24 H16 Cl12 N2 O4'
_chemical_formula_moiety         'C24 H16 Cl12 N2 O4'
_chemical_formula_sum            'C24 H16 Cl12 N2 O4'
_chemical_formula_weight         821.79
_chemical_name_systematic
(3aR,4S,7S,7aS)-4,5,6,7,8,8-Hexachloro-2-{6-[(3aR,4R,7R,7aS)-4,5,6,7,8,8-hexachloro-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl]hexyl}-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 103.4990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9549(3)
_cell_length_b                   10.5908(4)
_cell_length_c                   16.6043(6)
_cell_measurement_reflns_used    7701
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.30
_cell_volume                     1531.24(10)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12567
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.178
_diffrn_reflns_theta_min         2.300
_exptl_absorpt_coefficient_mu    1.122
_exptl_absorpt_correction_T_max  0.736
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_description       block
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0207
_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)+(0.0231P)²+0.7545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0514
_refine_ls_wR_factor_ref         0.0529
_reflns_number_gt                3141
_reflns_number_total             3403
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2251sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243866
_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   0.702
_shelx_estimated_absorpt_t_max   0.744
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.81506(4) 0.38645(3) 0.33748(2) 0.02092(8) Uani d 1 . .
Cl Cl2 0.65657(4) 0.08552(3) 0.31569(2) 0.02036(8) Uani d 1 . .
Cl Cl3 0.45141(4) 0.28198(3) 0.24334(2) 0.01993(8) Uani d 1 . .
Cl Cl4 0.48797(4) 0.05628(3) 0.10287(2) 0.02218(8) Uani d 1 . .
Cl Cl5 0.75019(4) 0.52267(3) 0.15453(2) 0.02455(9) Uani d 1 . .
Cl Cl6 0.55737(5) 0.31532(4) 0.00843(2) 0.02966(9) Uani d 1 . .
O O1 1.10843(11) 0.32935(10) 0.22625(6) 0.0224(2) Uani d 1 . .
O O2 0.83761(12) 0.05643(10) 0.03360(6) 0.0220(2) Uani d 1 . .
N N1 0.99701(12) 0.19567(11) 0.11936(7) 0.0156(2) Uani d 1 . .
C C1 1.01234(15) 0.25177(13) 0.19624(8) 0.0152(3) Uani d 1 . .
C C2 0.88902(15) 0.19800(12) 0.23555(8) 0.0139(2) Uani d 1 . .
H H2 0.935586 0.153877 0.288724 0.017 Uiso calc 1 . .
C C3 0.76483(15) 0.29560(12) 0.24743(8) 0.0142(2) Uani d 1 . .
C C4 0.62421(15) 0.20595(12) 0.24022(8) 0.0142(2) Uani d 1 . .
C C5 0.63197(15) 0.15971(12) 0.15208(8) 0.0140(2) Uani d 1 . .
C C6 0.79769(15) 0.10488(12) 0.17088(8) 0.0142(2) Uani d 1 . .
H H6 0.801142 0.017191 0.193567 0.017 Uiso calc 1 . .
C C7 0.87382(15) 0.11223(12) 0.09843(8) 0.0153(3) Uani d 1 . .
C C8 0.71121(15) 0.36779(12) 0.16671(8) 0.0153(3) Uani d 1 . .
C C9 0.63396(15) 0.28797(13) 0.11034(8) 0.0157(3) Uani d 1 . .
C C10 1.09720(16) 0.21915(14) 0.06241(8) 0.0200(3) Uani d 1 . .
H H10A 1.112615 0.139247 0.034488 0.024 Uiso calc 1 . .
H H10B 1.198763 0.248383 0.094445 0.024 Uiso calc 1 . .
C C11 1.02959(17) 0.31780(14) -0.00267(8) 0.0213(3) Uani d 1 . .
H H11A 1.081293 0.311153 -0.049094 0.026 Uiso calc 1 . .
H H11B 0.919312 0.299100 -0.024805 0.026 Uiso calc 1 . .
C C12 1.04563(18) 0.45260(13) 0.03013(8) 0.0223(3) Uani d 1 . .
H H12A 1.010849 0.455925 0.082477 0.027 Uiso calc 1 . .
H H12B 1.155427 0.476794 0.042781 0.027 Uiso calc 1 . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C7 . . 113.85(11) ?
C1 N1 C10 . . 125.21(11) ?
C7 N1 C10 . . 120.94(11) ?
O1 C1 N1 . . 125.37(13) ?
O1 C1 C2 . . 126.60(12) ?
N1 C1 C2 . . 108.03(11) ?
C1 C2 C6 . . 105.12(10) ?
C1 C2 C3 . . 114.59(11) ?
C6 C2 C3 . . 103.47(10) ?
C1 C2 H2 . . 111.1 ?
C6 C2 H2 . . 111.1 ?
C3 C2 H2 . . 111.1 ?
C8 C3 C4 . . 98.94(10) ?
C8 C3 C2 . . 107.98(10) ?
C4 C3 C2 . . 99.97(10) ?
C8 C3 Cl1 . . 116.29(9) ?
C4 C3 Cl1 . . 116.31(9) ?
C2 C3 Cl1 . . 115.05(9) ?
C3 C4 C5 . . 92.94(9) ?
C3 C4 Cl3 . . 114.83(9) ?
C5 C4 Cl3 . . 113.84(9) ?
C3 C4 Cl2 . . 112.95(9) ?
C5 C4 Cl2 . . 113.80(9) ?
Cl3 C4 Cl2 . . 108.08(7) ?
C9 C5 C6 . . 108.14(10) ?
C9 C5 C4 . . 98.88(10) ?
C6 C5 C4 . . 100.27(9) ?
C9 C5 Cl4 . . 115.59(9) ?
C6 C5 Cl4 . . 115.22(9) ?
C4 C5 Cl4 . . 116.55(9) ?
C7 C6 C2 . . 104.81(10) ?
C7 C6 C5 . . 113.96(10) ?
C2 C6 C5 . . 103.10(10) ?
C7 C6 H6 . . 111.5 ?
C2 C6 H6 . . 111.5 ?
C5 C6 H6 . . 111.5 ?
O2 C7 N1 . . 124.52(13) ?
O2 C7 C6 . . 127.35(12) ?
N1 C7 C6 . . 108.13(11) ?
C9 C8 C3 . . 107.83(11) ?
C9 C8 Cl5 . . 128.16(11) ?
C3 C8 Cl5 . . 124.00(10) ?
C8 C9 C5 . . 107.78(11) ?
C8 C9 Cl6 . . 128.08(11) ?
C5 C9 Cl6 . . 124.06(10) ?
N1 C10 C11 . . 111.81(11) ?
N1 C10 H10A . . 109.3 ?
C11 C10 H10A . . 109.3 ?
N1 C10 H10B . . 109.3 ?
C11 C10 H10B . . 109.3 ?
H10A C10 H10B . . 107.9 ?
C12 C11 C10 . . 113.62(11) ?
C12 C11 H11A . . 108.8 ?
C10 C11 H11A . . 108.8 ?
C12 C11 H11B . . 108.8 ?
C10 C11 H11B . . 108.8 ?
H11A C11 H11B . . 107.7 ?
C12 C12 C11 3_765 . 113.19(14) ?
C12 C12 H12A 3_765 . 108.9 ?
C11 C12 H12A . . 108.9 ?
C12 C12 H12B 3_765 . 108.9 ?
C11 C12 H12B . . 108.9 ?
H12A C12 H12B . . 107.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 . 1.7464(13) ?
Cl2 C4 . 1.7639(13) ?
Cl3 C4 . 1.7558(13) ?
Cl4 C5 . 1.7432(13) ?
Cl5 C8 . 1.6989(14) ?
Cl6 C9 . 1.6958(13) ?
O1 C1 . 1.2098(17) ?
O2 C7 . 1.2042(16) ?
N1 C1 . 1.3855(16) ?
N1 C7 . 1.3927(17) ?
N1 C10 . 1.4686(17) ?
C1 C2 . 1.5186(19) ?
C2 C6 . 1.5442(17) ?
C2 C3 . 1.5642(17) ?
C2 H2 . 1.0000 ?
C3 C8 . 1.5203(17) ?
C3 C4 . 1.5592(18) ?
C4 C5 . 1.5599(17) ?
C5 C9 . 1.5269(18) ?
C5 C6 . 1.5559(18) ?
C6 C7 . 1.5168(18) ?
C6 H6 . 1.0000 ?
C8 C9 . 1.3293(19) ?
C10 C11 . 1.523(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.5228(19) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C12 3_765 1.515(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H6 O1 2_745 1.00 2.43 3.3867(16) 161 yes
C10 H10A O2 3_755 0.99 2.45 3.4402(17) 178 yes
C12 H12B Cl2 2_755 0.99 2.80 3.5299(15) 131 yes
C3 Cl1 Cg1 2_755 1.7464(13) 3.8854(7) 4.9389(14) 117.41(5) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 O1 . . . . -178.12(13) ?
C10 N1 C1 O1 . . . . 1.4(2) ?
C7 N1 C1 C2 . . . . 2.31(14) ?
C10 N1 C1 C2 . . . . -178.13(11) ?
O1 C1 C2 C6 . . . . 179.44(13) ?
N1 C1 C2 C6 . . . . -1.01(13) ?
O1 C1 C2 C3 . . . . 66.54(17) ?
N1 C1 C2 C3 . . . . -113.90(12) ?
C1 C2 C3 C8 . . . . 47.50(14) ?
C6 C2 C3 C8 . . . . -66.37(12) ?
C1 C2 C3 C4 . . . . 150.38(10) ?
C6 C2 C3 C4 . . . . 36.51(11) ?
C1 C2 C3 Cl1 . . . . -84.24(12) ?
C6 C2 C3 Cl1 . . . . 161.89(9) ?
C8 C3 C4 C5 . . . . 52.32(10) ?
C2 C3 C4 C5 . . . . -57.86(10) ?
Cl1 C3 C4 C5 . . . . 177.63(9) ?
C8 C3 C4 Cl3 . . . . -65.69(11) ?
C2 C3 C4 Cl3 . . . . -175.87(8) ?
Cl1 C3 C4 Cl3 . . . . 59.62(12) ?
C8 C3 C4 Cl2 . . . . 169.74(9) ?
C2 C3 C4 Cl2 . . . . 59.57(11) ?
Cl1 C3 C4 Cl2 . . . . -64.95(11) ?
C3 C4 C5 C9 . . . . -51.85(10) ?
Cl3 C4 C5 C9 . . . . 66.99(11) ?
Cl2 C4 C5 C9 . . . . -168.55(9) ?
C3 C4 C5 C6 . . . . 58.55(10) ?
Cl3 C4 C5 C6 . . . . 177.40(9) ?
Cl2 C4 C5 C6 . . . . -58.15(11) ?
C3 C4 C5 Cl4 . . . . -176.38(9) ?
Cl3 C4 C5 Cl4 . . . . -57.54(12) ?
Cl2 C4 C5 Cl4 . . . . 66.92(11) ?
C1 C2 C6 C7 . . . . -0.47(13) ?
C3 C2 C6 C7 . . . . 120.07(11) ?
C1 C2 C6 C5 . . . . -119.99(10) ?
C3 C2 C6 C5 . . . . 0.55(12) ?
C9 C5 C6 C7 . . . . -47.46(14) ?
C4 C5 C6 C7 . . . . -150.44(11) ?
Cl4 C5 C6 C7 . . . . 83.59(12) ?
C9 C5 C6 C2 . . . . 65.53(12) ?
C4 C5 C6 C2 . . . . -37.45(12) ?
Cl4 C5 C6 C2 . . . . -163.42(9) ?
C1 N1 C7 O2 . . . . 177.78(13) ?
C10 N1 C7 O2 . . . . -1.8(2) ?
C1 N1 C7 C6 . . . . -2.63(15) ?
C10 N1 C7 C6 . . . . 177.79(11) ?
C2 C6 C7 O2 . . . . -178.64(13) ?
C5 C6 C7 O2 . . . . -66.68(18) ?
C2 C6 C7 N1 . . . . 1.79(13) ?
C5 C6 C7 N1 . . . . 113.75(12) ?
C4 C3 C8 C9 . . . . -35.34(13) ?
C2 C3 C8 C9 . . . . 68.27(13) ?
Cl1 C3 C8 C9 . . . . -160.66(10) ?
C4 C3 C8 Cl5 . . . . 145.71(10) ?
C2 C3 C8 Cl5 . . . . -110.68(11) ?
Cl1 C3 C8 Cl5 . . . . 20.39(15) ?
C3 C8 C9 C5 . . . . 0.64(14) ?
Cl5 C8 C9 C5 . . . . 179.54(10) ?
C3 C8 C9 Cl6 . . . . -176.19(10) ?
Cl5 C8 C9 Cl6 . . . . 2.7(2) ?
C6 C5 C9 C8 . . . . -69.69(13) ?
C4 C5 C9 C8 . . . . 34.26(13) ?
Cl4 C5 C9 C8 . . . . 159.47(10) ?
C6 C5 C9 Cl6 . . . . 107.30(11) ?
C4 C5 C9 Cl6 . . . . -148.75(10) ?
Cl4 C5 C9 Cl6 . . . . -23.54(15) ?
C1 N1 C10 C11 . . . . -96.26(15) ?
C7 N1 C10 C11 . . . . 83.27(15) ?
N1 C10 C11 C12 . . . . 76.43(15) ?
C10 C11 C12 C12 . . . 3_765 -169.86(15) ?

_cod_database_fobs_code 2243866
