#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/78/2227847.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_2227847
loop_
_publ_author_name
'Yao, Zhi-Gang'
'Peng, Jun-Mei'
'Huo, Su-Fang'
'Hu, Ai-Xi'
_publ_section_title
;
 2-[4-tert-Butyl-5-(2-chlorobenzyl)-1,3-thiazol-2-yl]isoindoline-1,3-dione
;
_journal_coeditor_code           NG5049
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2940
_journal_paper_doi               10.1107/S1600536810042601
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H19 Cl N2 O2 S'
_chemical_formula_moiety         'C22 H19 Cl N2 O2 S'
_chemical_formula_sum            'C22 H19 Cl N2 O2 S'
_chemical_formula_weight         410.90
_chemical_melting_point          425
_chemical_name_systematic
;
2-[4-tert-Butyl-5-(2-chlorobenzyl)-1,3-thiazol-2-yl]isoindoline-1,3-dione
;
_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                100.4040(10)
_cell_angle_beta                 95.8970(10)
_cell_angle_gamma                96.4900(10)
_cell_formula_units_Z            2
_cell_length_a                   7.8357(4)
_cell_length_b                   8.1587(4)
_cell_length_c                   16.1487(8)
_cell_measurement_reflns_used    5125
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.56
_cell_volume                     1000.85(9)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       ω
_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  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7798
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.9168
_exptl_absorpt_correction_T_min  0.8684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0649P)²+0.4002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1220
_reflns_number_gt                3268
_reflns_number_total             3857
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5049.cif
_cod_data_source_block           I
_cod_database_code               2227847
_cod_database_fobs_code          2227847
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.47492(7) -0.21014(8) 0.32706(3) 0.04128(18) Uani d . 1 . .
S S1 0.02664(6) 0.03724(6) 0.16354(3) 0.02634(15) Uani d . 1 . .
C C1 0.2305(2) 0.1497(2) 0.18229(12) 0.0236(4) Uani d . 1 . .
C C2 0.1795(3) 0.1461(2) 0.31377(12) 0.0266(4) Uani d . 1 . .
C C3 0.0266(2) 0.0574(2) 0.27220(12) 0.0239(4) Uani d . 1 . .
C C4 0.2332(3) 0.1918(3) 0.40993(13) 0.0366(5) Uani d . 1 . .
C C5 0.4226(4) 0.2725(4) 0.42868(16) 0.0624(9) Uani d . 1 . .
H H5A 0.4953 0.1967 0.3993 0.094 Uiso calc R 1 . .
H H5B 0.4592 0.2932 0.4900 0.094 Uiso calc R 1 . .
H H5C 0.4347 0.3793 0.4088 0.094 Uiso calc R 1 . .
C C6 0.2175(3) 0.0330(3) 0.44847(14) 0.0389(5) Uani d . 1 . .
H H6A 0.0978 -0.0232 0.4360 0.058 Uiso calc R 1 . .
H H6B 0.2495 0.0640 0.5101 0.058 Uiso calc R 1 . .
H H6C 0.2950 -0.0434 0.4240 0.058 Uiso calc R 1 . .
C C7 0.1182(4) 0.3151(3) 0.45113(15) 0.0555(7) Uani d . 1 . .
H H7A 0.1307 0.4177 0.4275 0.083 Uiso calc R 1 . .
H H7B 0.1534 0.3433 0.5126 0.083 Uiso calc R 1 . .
H H7C -0.0029 0.2630 0.4396 0.083 Uiso calc R 1 . .
C C8 -0.1313(2) -0.0235(2) 0.30286(12) 0.0261(4) Uani d . 1 . .
H H8A -0.2359 0.0057 0.2720 0.031 Uiso calc R 1 . .
H H8B -0.1298 0.0241 0.3639 0.031 Uiso calc R 1 . .
C C9 -0.1445(2) -0.2135(2) 0.29113(12) 0.0255(4) Uani d . 1 . .
C C10 -0.2985(3) -0.3103(3) 0.29935(12) 0.0298(4) Uani d . 1 . .
C C11 -0.3166(3) -0.4842(3) 0.28567(15) 0.0422(6) Uani d . 1 . .
H H11 -0.4235 -0.5467 0.2909 0.051 Uiso calc R 1 . .
C C12 -0.1785(4) -0.5656(3) 0.26456(18) 0.0510(7) Uani d . 1 . .
H H12 -0.1901 -0.6849 0.2547 0.061 Uiso calc R 1 . .
C C13 -0.0231(3) -0.4749(3) 0.25766(18) 0.0492(6) Uani d . 1 . .
H H13 0.0730 -0.5313 0.2441 0.059 Uiso calc R 1 . .
C C14 -0.0074(3) -0.3009(3) 0.27052(15) 0.0349(5) Uani d . 1 . .
H H14 0.1001 -0.2396 0.2651 0.042 Uiso calc R 1 . .
C C15 0.4999(2) 0.1549(2) 0.11270(12) 0.0248(4) Uani d . 1 . .
C C16 0.5493(2) 0.2158(2) 0.03643(12) 0.0245(4) Uani d . 1 . .
C C17 0.7093(3) 0.2341(3) 0.00803(14) 0.0306(4) Uani d . 1 . .
H H17 0.8079 0.2015 0.0369 0.037 Uiso calc R 1 . .
C C18 0.7203(3) 0.3020(3) -0.06437(13) 0.0319(5) Uani d . 1 . .
H H18 0.8292 0.3190 -0.0847 0.038 Uiso calc R 1 . .
C C19 0.5758(3) 0.3453(3) -0.10749(13) 0.0307(4) Uani d . 1 . .
H H19 0.5873 0.3896 -0.1574 0.037 Uiso calc R 1 . .
C C20 0.4131(2) 0.3257(3) -0.07953(12) 0.0270(4) Uani d . 1 . .
H H20 0.3135 0.3546 -0.1094 0.032 Uiso calc R 1 . .
C C21 0.4048(2) 0.2618(2) -0.00597(11) 0.0228(4) Uani d . 1 . .
C C22 0.2572(2) 0.2381(2) 0.04291(12) 0.0249(4) Uani d . 1 . .
N N1 0.2936(2) 0.2002(2) 0.26111(10) 0.0276(4) Uani d . 1 . .
N N2 0.3239(2) 0.1807(2) 0.11564(10) 0.0244(3) Uani d . 1 . .
O O1 0.58277(18) 0.09357(19) 0.16259(9) 0.0334(3) Uani d . 1 . .
O O2 0.10930(18) 0.2615(2) 0.02800(9) 0.0374(4) Uani d . 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'
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C3 . . 88.77(9) ?
N1 C1 N2 . . 122.33(17) ?
N1 C1 S1 . . 115.89(14) ?
N2 C1 S1 . . 121.76(14) ?
C3 C2 N1 . . 114.54(17) ?
C3 C2 C4 . . 127.00(18) ?
N1 C2 C4 . . 118.45(17) ?
C2 C3 C8 . . 132.65(17) ?
C2 C3 S1 . . 109.93(14) ?
C8 C3 S1 . . 117.41(14) ?
C5 C4 C2 . . 109.70(17) ?
C5 C4 C6 . . 107.7(2) ?
C2 C4 C6 . . 110.24(18) ?
C5 C4 C7 . . 109.5(2) ?
C2 C4 C7 . . 110.09(19) ?
C6 C4 C7 . . 109.56(19) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C4 C6 H6A . . 109.5 ?
C4 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C4 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C3 C8 C9 . . 113.97(16) ?
C3 C8 H8A . . 108.8 ?
C9 C8 H8A . . 108.8 ?
C3 C8 H8B . . 108.8 ?
C9 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.7 ?
C14 C9 C10 . . 116.45(19) ?
C14 C9 C8 . . 122.59(17) ?
C10 C9 C8 . . 120.96(18) ?
C11 C10 C9 . . 122.3(2) ?
C11 C10 Cl1 . . 118.45(17) ?
C9 C10 Cl1 . . 119.27(16) ?
C12 C11 C10 . . 119.4(2) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C11 C12 C13 . . 120.3(2) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C12 C13 C14 . . 119.8(2) ?
C12 C13 H13 . . 120.1 ?
C14 C13 H13 . . 120.1 ?
C13 C14 C9 . . 121.9(2) ?
C13 C14 H14 . . 119.1 ?
C9 C14 H14 . . 119.1 ?
O1 C15 N2 . . 124.78(18) ?
O1 C15 C16 . . 129.95(18) ?
N2 C15 C16 . . 105.26(15) ?
C17 C16 C21 . . 121.50(18) ?
C17 C16 C15 . . 129.50(18) ?
C21 C16 C15 . . 108.97(16) ?
C16 C17 C18 . . 117.32(18) ?
C16 C17 H17 . . 121.3 ?
C18 C17 H17 . . 121.3 ?
C19 C18 C17 . . 121.24(18) ?
C19 C18 H18 . . 119.4 ?
C17 C18 H18 . . 119.4 ?
C18 C19 C20 . . 121.71(19) ?
C18 C19 H19 . . 119.1 ?
C20 C19 H19 . . 119.1 ?
C21 C20 C19 . . 116.44(18) ?
C21 C20 H20 . . 121.8 ?
C19 C20 H20 . . 121.8 ?
C20 C21 C16 . . 121.75(17) ?
C20 C21 C22 . . 129.59(17) ?
C16 C21 C22 . . 108.59(16) ?
O2 C22 N2 . . 124.31(18) ?
O2 C22 C21 . . 129.93(18) ?
N2 C22 C21 . . 105.75(15) ?
C1 N1 C2 . . 110.85(16) ?
C1 N2 C22 . . 125.37(16) ?
C1 N2 C15 . . 123.47(15) ?
C22 N2 C15 . . 111.15(15) ?
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 C10 . 1.741(2) ?
S1 C1 . 1.7188(19) ?
S1 C3 . 1.7327(19) ?
C1 N1 . 1.292(2) ?
C1 N2 . 1.406(2) ?
C2 C3 . 1.369(3) ?
C2 N1 . 1.385(2) ?
C2 C4 . 1.532(3) ?
C3 C8 . 1.507(3) ?
C4 C5 . 1.531(3) ?
C4 C6 . 1.534(3) ?
C4 C7 . 1.534(3) ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 C9 . 1.518(3) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C14 . 1.391(3) ?
C9 C10 . 1.397(3) ?
C10 C11 . 1.385(3) ?
C11 C12 . 1.373(4) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.377(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.386(3) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 O1 . 1.197(2) ?
C15 N2 . 1.422(2) ?
C15 C16 . 1.480(3) ?
C16 C17 . 1.380(3) ?
C16 C21 . 1.386(3) ?
C17 C18 . 1.388(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.382(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.398(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.385(3) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.480(3) ?
C22 O2 . 1.203(2) ?
C22 N2 . 1.414(2) ?
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
C3 S1 C1 N1 . . . . -0.76(16) ?
C3 S1 C1 N2 . . . . 177.63(16) ?
N1 C2 C3 C8 . . . . -179.96(18) ?
C4 C2 C3 C8 . . . . -0.9(4) ?
N1 C2 C3 S1 . . . . 1.1(2) ?
C4 C2 C3 S1 . . . . -179.79(17) ?
C1 S1 C3 C2 . . . . -0.25(15) ?
C1 S1 C3 C8 . . . . -179.33(15) ?
C3 C2 C4 C5 . . . . 173.1(2) ?
N1 C2 C4 C5 . . . . -7.9(3) ?
C3 C2 C4 C6 . . . . 54.6(3) ?
N1 C2 C4 C6 . . . . -126.4(2) ?
C3 C2 C4 C7 . . . . -66.4(3) ?
N1 C2 C4 C7 . . . . 112.6(2) ?
C2 C3 C8 C9 . . . . -104.1(2) ?
S1 C3 C8 C9 . . . . 74.74(19) ?
C3 C8 C9 C14 . . . . 12.5(3) ?
C3 C8 C9 C10 . . . . -166.43(18) ?
C14 C9 C10 C11 . . . . -1.7(3) ?
C8 C9 C10 C11 . . . . 177.34(19) ?
C14 C9 C10 Cl1 . . . . 178.77(15) ?
C8 C9 C10 Cl1 . . . . -2.2(3) ?
C9 C10 C11 C12 . . . . 1.0(3) ?
Cl1 C10 C11 C12 . . . . -179.38(19) ?
C10 C11 C12 C13 . . . . 0.5(4) ?
C11 C12 C13 C14 . . . . -1.2(4) ?
C12 C13 C14 C9 . . . . 0.6(4) ?
C10 C9 C14 C13 . . . . 0.8(3) ?
C8 C9 C14 C13 . . . . -178.1(2) ?
O1 C15 C16 C17 . . . . -7.7(4) ?
N2 C15 C16 C17 . . . . 173.5(2) ?
O1 C15 C16 C21 . . . . 174.3(2) ?
N2 C15 C16 C21 . . . . -4.5(2) ?
C21 C16 C17 C18 . . . . 0.6(3) ?
C15 C16 C17 C18 . . . . -177.14(19) ?
C16 C17 C18 C19 . . . . -1.7(3) ?
C17 C18 C19 C20 . . . . 1.1(3) ?
C18 C19 C20 C21 . . . . 0.5(3) ?
C19 C20 C21 C16 . . . . -1.6(3) ?
C19 C20 C21 C22 . . . . 175.01(18) ?
C17 C16 C21 C20 . . . . 1.1(3) ?
C15 C16 C21 C20 . . . . 179.23(17) ?
C17 C16 C21 C22 . . . . -176.19(18) ?
C15 C16 C21 C22 . . . . 2.0(2) ?
C20 C21 C22 O2 . . . . 3.8(4) ?
C16 C21 C22 O2 . . . . -179.2(2) ?
C20 C21 C22 N2 . . . . -175.65(19) ?
C16 C21 C22 N2 . . . . 1.3(2) ?
N2 C1 N1 C2 . . . . -176.86(17) ?
S1 C1 N1 C2 . . . . 1.5(2) ?
C3 C2 N1 C1 . . . . -1.7(2) ?
C4 C2 N1 C1 . . . . 179.14(18) ?
N1 C1 N2 C22 . . . . -134.9(2) ?
S1 C1 N2 C22 . . . . 46.8(2) ?
N1 C1 N2 C15 . . . . 46.1(3) ?
S1 C1 N2 C15 . . . . -132.20(17) ?
O2 C22 N2 C1 . . . . -2.9(3) ?
C21 C22 N2 C1 . . . . 176.62(16) ?
O2 C22 N2 C15 . . . . 176.22(19) ?
C21 C22 N2 C15 . . . . -4.3(2) ?
O1 C15 N2 C1 . . . . 5.6(3) ?
C16 C15 N2 C1 . . . . -175.46(16) ?
O1 C15 N2 C22 . . . . -173.47(19) ?
C16 C15 N2 C22 . . . . 5.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26231247
