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#$Date: 2023-03-02 10:29:09 +0200 (Thu, 02 Mar 2023) $
#$Revision: 281241 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106810.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_8106810
loop_
_publ_author_name
'Li, Feng-Cui'
'Shi, Qi-Lin'
'Zhou, Xiao-Hu'
'Ren, Yang'
'Xu, Hai'
_publ_section_title
;
 Crystal structure of
 2-(4-acetyl-2,6-dimethyl-phenyl)-5,6-dichloro-isoindole-1,3-dione,
 C18H13Cl2NO3
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              149
_journal_page_last               151
_journal_paper_doi               10.1515/ncrs-2015-0064
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C18 H13 Cl2 N O3'
_chemical_formula_sum            'C18 H13 Cl2 N O3'
_chemical_formula_weight         362.19
_chemical_name_common
2-(4-Acetyl-2,6-dimethyl-phenyl)-5,6-dichloro-isoindole-1,3-dione
_chemical_name_systematic
;
2-(4-Acetyl-2,6-dimethyl-phenyl)-5,6-dichloro-isoindole-1,3-dione
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 107.5570(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.6464(2)
_cell_length_b                   18.1592(3)
_cell_length_c                   13.9829(2)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.50
_cell_volume                     3303.66(9)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22286
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.9227
_exptl_absorpt_correction_T_min  0.8872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         6472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0362P)²+1.8874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                5809
_reflns_number_total             6472
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0064_suppl.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               8106810
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.35842(11) 0.69155(8) 0.69857(10) 0.0205(3) Uani 1 1 d . . .
C2 C 0.45538(11) 0.69454(8) 0.68474(10) 0.0208(3) Uani 1 1 d . . .
C3 C 0.47653(11) 0.65522(8) 0.60769(11) 0.0206(3) Uani 1 1 d . . .
H3 H 0.5407 0.6574 0.5974 0.025 Uiso 1 1 calc R . .
C4 C 0.39815(10) 0.61298(7) 0.54737(10) 0.0181(3) Uani 1 1 d . . .
C5 C 0.30367(10) 0.60775(8) 0.56434(10) 0.0192(3) Uani 1 1 d . . .
C6 C 0.28121(11) 0.64672(8) 0.63959(10) 0.0205(3) Uani 1 1 d . . .
H6 H 0.2174 0.6432 0.6504 0.025 Uiso 1 1 calc R . .
C7 C 0.23758(11) 0.55690(8) 0.48889(11) 0.0212(3) Uani 1 1 d . . .
C9 C 0.39523(11) 0.56728(8) 0.45803(10) 0.0188(3) Uani 1 1 d . . .
C10 C 0.26379(10) 0.48193(8) 0.34832(10) 0.0174(3) Uani 1 1 d . . .
C11 C 0.25974(10) 0.40774(8) 0.37473(10) 0.0181(3) Uani 1 1 d . . .
C12 C 0.22929(10) 0.35645(8) 0.29812(10) 0.0187(3) Uani 1 1 d . . .
H12 H 0.2269 0.3068 0.3138 0.022 Uiso 1 1 calc R . .
C13 C 0.20217(10) 0.37810(8) 0.19782(10) 0.0194(3) Uani 1 1 d . . .
C14 C 0.20514(11) 0.45238(8) 0.17397(10) 0.0196(3) Uani 1 1 d . . .
H14 H 0.1858 0.4667 0.1070 0.024 Uiso 1 1 calc R . .
C15 C 0.23669(10) 0.50572(8) 0.24903(10) 0.0186(3) Uani 1 1 d . . .
C16 C 0.28845(11) 0.38398(9) 0.48274(10) 0.0235(3) Uani 1 1 d . . .
H16A H 0.2832 0.3314 0.4861 0.035 Uiso 1 1 calc R . .
H16B H 0.2427 0.4065 0.5145 0.035 Uiso 1 1 calc R . .
H16C H 0.3578 0.3989 0.5166 0.035 Uiso 1 1 calc R . .
C17 C 0.23991(12) 0.58589(8) 0.22266(11) 0.0254(3) Uani 1 1 d . . .
H17A H 0.2052 0.5927 0.1525 0.038 Uiso 1 1 calc R . .
H17B H 0.3101 0.6015 0.2373 0.038 Uiso 1 1 calc R . .
H17C H 0.2064 0.6146 0.2613 0.038 Uiso 1 1 calc R . .
C18 C 0.16916(12) 0.31915(9) 0.11901(11) 0.0260(3) Uani 1 1 d . . .
C19 C 0.12712(17) 0.34234(10) 0.01141(12) 0.0426(5) Uani 1 1 d . . .
H19A H 0.1012 0.3000 -0.0295 0.064 Uiso 1 1 calc R . .
H19B H 0.1808 0.3647 -0.0099 0.064 Uiso 1 1 calc R . .
H19C H 0.0725 0.3771 0.0047 0.064 Uiso 1 1 calc R . .
C21 C 0.97223(11) 0.96336(8) 0.36036(10) 0.0201(3) Uani 1 1 d . . .
C22 C 0.87587(11) 0.97215(8) 0.37432(11) 0.0218(3) Uani 1 1 d . . .
C23 C 0.84346(11) 0.92703(8) 0.43961(11) 0.0212(3) Uani 1 1 d . . .
H23 H 0.7789 0.9323 0.4483 0.025 Uiso 1 1 calc R . .
C24 C 0.91199(11) 0.87428(7) 0.49066(10) 0.0179(3) Uani 1 1 d . . .
C25 C 1.00867(11) 0.86713(7) 0.47919(10) 0.0191(3) Uani 1 1 d . . .
C26 C 1.04109(11) 0.91092(8) 0.41426(11) 0.0211(3) Uani 1 1 d . . .
H26 H 1.1062 0.9056 0.4068 0.025 Uiso 1 1 calc R . .
C27 C 1.06207(11) 0.80419(8) 0.54186(11) 0.0216(3) Uani 1 1 d . . .
C29 C 0.89757(11) 0.81439(8) 0.55813(10) 0.0191(3) Uani 1 1 d . . .
C30 C 1.00940(10) 0.71054(7) 0.64791(10) 0.0189(3) Uani 1 1 d . . .
C31 C 0.99695(10) 0.64272(8) 0.59934(10) 0.0179(3) Uani 1 1 d . . .
C32 C 1.01393(10) 0.57950(8) 0.65855(10) 0.0178(3) Uani 1 1 d . . .
H32 H 1.0054 0.5335 0.6280 0.021 Uiso 1 1 calc R . .
C33 C 1.04341(10) 0.58422(8) 0.76263(10) 0.0182(3) Uani 1 1 d . . .
C34 C 1.05622(11) 0.65312(8) 0.80846(10) 0.0216(3) Uani 1 1 d . . .
H34 H 1.0771 0.6561 0.8781 0.026 Uiso 1 1 calc R . .
C35 C 1.03834(11) 0.71752(8) 0.75213(11) 0.0221(3) Uani 1 1 d . . .
C36 C 0.96468(12) 0.63734(8) 0.48693(11) 0.0245(3) Uani 1 1 d . . .
H36A H 1.0189 0.6554 0.4627 0.037 Uiso 1 1 calc R . .
H36B H 0.9039 0.6664 0.4591 0.037 Uiso 1 1 calc R . .
H36C H 0.9506 0.5869 0.4672 0.037 Uiso 1 1 calc R . .
C37 C 1.04770(15) 0.79166(9) 0.80188(12) 0.0336(4) Uani 1 1 d . . .
H37A H 1.0718 0.7856 0.8734 0.050 Uiso 1 1 calc R . .
H37B H 0.9817 0.8153 0.7832 0.050 Uiso 1 1 calc R . .
H37C H 1.0956 0.8214 0.7808 0.050 Uiso 1 1 calc R . .
C38 C 1.05900(11) 0.51677(8) 0.82675(10) 0.0207(3) Uani 1 1 d . . .
C39 C 1.02620(12) 0.44366(8) 0.77690(12) 0.0274(3) Uani 1 1 d . . .
H39A H 1.0751 0.4278 0.7442 0.041 Uiso 1 1 calc R . .
H39B H 0.9597 0.4485 0.7282 0.041 Uiso 1 1 calc R . .
H39C H 1.0228 0.4080 0.8265 0.041 Uiso 1 1 calc R . .
N1 N 0.29703(9) 0.53502(7) 0.42776(9) 0.0195(2) Uani 1 1 d . . .
N2 N 0.99150(9) 0.77612(6) 0.58751(9) 0.0201(2) Uani 1 1 d . . .
O1 O 0.15112(8) 0.53703(7) 0.47978(8) 0.0304(3) Uani 1 1 d . . .
O2 O 0.46034(8) 0.55874(6) 0.41719(8) 0.0261(2) Uani 1 1 d . . .
O3 O 0.17622(10) 0.25459(6) 0.14199(9) 0.0362(3) Uani 1 1 d . . .
O4 O 1.14673(8) 0.78024(6) 0.55197(9) 0.0326(3) Uani 1 1 d . . .
O5 O 0.82262(8) 0.79891(6) 0.58173(8) 0.0272(2) Uani 1 1 d . . .
O6 O 1.09765(9) 0.52141(6) 0.91730(8) 0.0280(2) Uani 1 1 d . . .
Cl1 Cl 0.33039(3) 0.74560(2) 0.78865(3) 0.02973(10) Uani 1 1 d . . .
Cl2 Cl 0.55214(3) 0.74776(2) 0.76193(3) 0.03003(10) Uani 1 1 d . . .
Cl3 Cl 1.00666(3) 1.01528(2) 0.27283(3) 0.02950(10) Uani 1 1 d . . .
Cl4 Cl 0.79385(3) 1.03979(2) 0.30874(3) 0.03719(11) 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 121.46(13) . .
C6 C1 Cl1 118.08(11) . .
C2 C1 Cl1 120.45(11) . .
C3 C2 C1 120.91(13) . .
C3 C2 Cl2 118.19(11) . .
C1 C2 Cl2 120.89(11) . .
C4 C3 C2 117.06(13) . .
C4 C3 H3 121.5 . .
C2 C3 H3 121.5 . .
C3 C4 C5 121.65(13) . .
C3 C4 C9 129.98(13) . .
C5 C4 C9 108.37(12) . .
C6 C5 C4 122.00(13) . .
C6 C5 C7 129.41(13) . .
C4 C5 C7 108.58(12) . .
C5 C6 C1 116.81(13) . .
C5 C6 H6 121.6 . .
C1 C6 H6 121.6 . .
O1 C7 N1 125.44(13) . .
O1 C7 C5 128.88(13) . .
N1 C7 C5 105.68(12) . .
O2 C9 N1 125.26(13) . .
O2 C9 C4 129.28(13) . .
N1 C9 C4 105.45(11) . .
C15 C10 C11 122.72(12) . .
C15 C10 N1 119.30(12) . .
C11 C10 N1 117.98(12) . .
C12 C11 C10 117.95(12) . .
C12 C11 C16 120.66(13) . .
C10 C11 C16 121.38(12) . .
C11 C12 C13 120.99(13) . .
C11 C12 H12 119.5 . .
C13 C12 H12 119.5 . .
C14 C13 C12 119.71(13) . .
C14 C13 C18 122.51(13) . .
C12 C13 C18 117.78(13) . .
C13 C14 C15 121.06(13) . .
C13 C14 H14 119.5 . .
C15 C14 H14 119.5 . .
C10 C15 C14 117.56(12) . .
C10 C15 C17 121.68(13) . .
C14 C15 C17 120.76(13) . .
C11 C16 H16A 109.5 . .
C11 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C11 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C17 H17A 109.5 . .
C15 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C15 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
O3 C18 C19 120.90(14) . .
O3 C18 C13 120.78(14) . .
C19 C18 C13 118.32(13) . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C26 C21 C22 120.94(13) . .
C26 C21 Cl3 118.47(11) . .
C22 C21 Cl3 120.55(11) . .
C23 C22 C21 121.51(13) . .
C23 C22 Cl4 118.87(11) . .
C21 C22 Cl4 119.62(11) . .
C24 C23 C22 116.61(13) . .
C24 C23 H23 121.7 . .
C22 C23 H23 121.7 . .
C23 C24 C25 121.84(13) . .
C23 C24 C29 129.52(13) . .
C25 C24 C29 108.52(12) . .
C26 C25 C24 122.01(13) . .
C26 C25 C27 129.32(13) . .
C24 C25 C27 108.57(12) . .
C25 C26 C21 117.03(13) . .
C25 C26 H26 121.5 . .
C21 C26 H26 121.5 . .
O4 C27 N2 125.64(13) . .
O4 C27 C25 128.96(13) . .
N2 C27 C25 105.39(12) . .
O5 C29 N2 125.58(13) . .
O5 C29 C24 129.16(13) . .
N2 C29 C24 105.23(11) . .
C31 C30 C35 122.97(13) . .
C31 C30 N2 118.18(12) . .
C35 C30 N2 118.85(12) . .
C30 C31 C32 117.72(12) . .
C30 C31 C36 121.47(12) . .
C32 C31 C36 120.80(13) . .
C33 C32 C31 120.99(13) . .
C33 C32 H32 119.5 . .
C31 C32 H32 119.5 . .
C32 C33 C34 119.56(13) . .
C32 C33 C38 121.41(13) . .
C34 C33 C38 119.00(12) . .
C35 C34 C33 121.27(13) . .
C35 C34 H34 119.4 . .
C33 C34 H34 119.4 . .
C34 C35 C30 117.47(13) . .
C34 C35 C37 121.03(13) . .
C30 C35 C37 121.49(13) . .
C31 C36 H36A 109.5 . .
C31 C36 H36B 109.5 . .
H36A C36 H36B 109.5 . .
C31 C36 H36C 109.5 . .
H36A C36 H36C 109.5 . .
H36B C36 H36C 109.5 . .
C35 C37 H37A 109.5 . .
C35 C37 H37B 109.5 . .
H37A C37 H37B 109.5 . .
C35 C37 H37C 109.5 . .
H37A C37 H37C 109.5 . .
H37B C37 H37C 109.5 . .
O6 C38 C33 120.34(13) . .
O6 C38 C39 121.18(13) . .
C33 C38 C39 118.48(12) . .
C38 C39 H39A 109.5 . .
C38 C39 H39B 109.5 . .
H39A C39 H39B 109.5 . .
C38 C39 H39C 109.5 . .
H39A C39 H39C 109.5 . .
H39B C39 H39C 109.5 . .
C7 N1 C9 111.90(11) . .
C7 N1 C10 123.75(11) . .
C9 N1 C10 124.21(11) . .
C27 N2 C29 112.22(11) . .
C27 N2 C30 123.38(12) . .
C29 N2 C30 124.02(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.389(2) .
C1 C2 1.395(2) .
C1 Cl1 1.7281(14) .
C2 C3 1.393(2) .
C2 Cl2 1.7270(14) .
C3 C4 1.378(2) .
C3 H3 0.9300 .
C4 C5 1.383(2) .
C4 C9 1.4902(19) .
C5 C6 1.3771(19) .
C5 C7 1.4850(19) .
C6 H6 0.9300 .
C7 O1 1.2032(18) .
C7 N1 1.4017(18) .
C9 O2 1.2024(17) .
C9 N1 1.4056(18) .
C10 C15 1.3931(19) .
C10 C11 1.403(2) .
C10 N1 1.4371(17) .
C11 C12 1.3853(19) .
C11 C16 1.5045(19) .
C12 C13 1.3948(19) .
C12 H12 0.9300 .
C13 C14 1.393(2) .
C13 C18 1.505(2) .
C14 C15 1.3973(19) .
C14 H14 0.9300 .
C15 C17 1.506(2) .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 O3 1.2117(19) .
C18 C19 1.500(2) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C21 C26 1.389(2) .
C21 C22 1.396(2) .
C21 Cl3 1.7190(14) .
C22 C23 1.394(2) .
C22 Cl4 1.7271(14) .
C23 C24 1.378(2) .
C23 H23 0.9300 .
C24 C25 1.382(2) .
C24 C29 1.4911(19) .
C25 C26 1.376(2) .
C25 C27 1.4900(19) .
C26 H26 0.9300 .
C27 O4 1.2022(18) .
C27 N2 1.4019(18) .
C29 O5 1.1991(17) .
C29 N2 1.4061(18) .
C30 C31 1.392(2) .
C30 C35 1.396(2) .
C30 N2 1.4376(17) .
C31 C32 1.3933(19) .
C31 C36 1.5022(19) .
C32 C33 1.3906(19) .
C32 H32 0.9300 .
C33 C34 1.393(2) .
C33 C38 1.4947(19) .
C34 C35 1.390(2) .
C34 H34 0.9300 .
C35 C37 1.503(2) .
C36 H36A 0.9600 .
C36 H36B 0.9600 .
C36 H36C 0.9600 .
C37 H37A 0.9600 .
C37 H37B 0.9600 .
C37 H37C 0.9600 .
C38 O6 1.2188(17) .
C38 C39 1.504(2) .
C39 H39A 0.9600 .
C39 H39B 0.9600 .
C39 H39C 0.9600 .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{43a5fcec-1fe3-4bd0-9d46-0dd20d21885d} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{43a5fcec-1fe3-4bd0-9d46-0dd20d21885d} '_publcif_info_datablock.publ_exptl'
