#------------------------------------------------------------------------------
#$Date: 2022-02-04 01:17:47 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272508 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/62/1566280.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_1566280
loop_
_publ_author_name
'Gao, Yang'
'Yang, Simin'
'She, Minwei'
'Nie, Jianhong'
'Huo, Yanping'
'Chen, Qian'
'Li, Xianwei'
'Hu, Xiao-Qiang'
_publ_section_title
;
 Practical synthesis of 3-aryl anthranils via an electrophilic aromatic
 substitution strategy
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC06565C
_journal_year                    2022
_chemical_formula_moiety         'C20 H14 N2 O S'
_chemical_formula_sum            'C20 H14 N2 O S'
_chemical_formula_weight         330.39
_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
_audit_creation_date             2021-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-05 deposited with the CCDC.	2022-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.5450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6620(4)
_cell_length_b                   10.0274(2)
_cell_length_c                   10.2923(3)
_cell_measurement_reflns_used    5972
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.69
_cell_volume                     1564.59(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      230.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_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  0.0341
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9101
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.435
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1335 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.8599.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0566P)²+0.2841P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2483
_reflns_number_total             3165
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc06565c2.cif
_cod_data_source_block           mo_20210630_gaoy_0ma_a
_cod_database_code               1566280
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C008(H008), C009(H009), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O)
2.b Idealised Me refined as rotating group:
 C00F(H00A,H00B,H00C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.67164(3) 0.56647(5) 0.76200(5) 0.04781(18) Uani 1 1 d . . . . .
O002 O 0.35422(9) 0.45783(15) 0.83220(14) 0.0586(4) Uani 1 1 d . . . . .
N003 N 0.67286(10) 0.35289(15) 0.56053(15) 0.0422(4) Uani 1 1 d . . . . .
C004 C 0.59288(11) 0.36358(16) 0.59676(17) 0.0375(4) Uani 1 1 d . . . . .
C005 C 0.44070(12) 0.30130(18) 0.57331(18) 0.0429(4) Uani 1 1 d . . . . .
H005 H 0.391621 0.249663 0.530359 0.051 Uiso 1 1 calc R . . . .
C006 C 0.58430(11) 0.45615(17) 0.69493(18) 0.0385(4) Uani 1 1 d . . . . .
C007 C 0.43269(12) 0.39253(18) 0.67135(18) 0.0411(4) Uani 1 1 d . . . . .
C008 C 0.50652(11) 0.46807(18) 0.73326(18) 0.0406(4) Uani 1 1 d . . . . .
H008 H 0.503109 0.527909 0.802073 0.049 Uiso 1 1 calc R . . . .
C009 C 0.51928(12) 0.28532(18) 0.53807(18) 0.0432(4) Uani 1 1 d . . . . .
H009 H 0.523565 0.220906 0.473654 0.052 Uiso 1 1 calc R . . . .
C00A C 0.75276(12) 0.36438(18) 0.66052(19) 0.0428(4) Uani 1 1 d . . . . .
C00B C 0.26235(12) 0.38959(18) 0.6437(2) 0.0449(5) Uani 1 1 d . . . . .
C00C C 0.34922(12) 0.41000(18) 0.70801(19) 0.0436(4) Uani 1 1 d . . . . .
C00D C 0.76047(12) 0.45870(18) 0.7630(2) 0.0439(4) Uani 1 1 d . . . . .
N00E N 0.26887(12) 0.4702(2) 0.8536(2) 0.0722(6) Uani 1 1 d . . . . .
C00F C 0.67440(14) 0.2756(2) 0.44074(19) 0.0515(5) Uani 1 1 d . . . . .
H00A H 0.675197 0.181218 0.461520 0.077 Uiso 1 1 calc GR . . . .
H00B H 0.726745 0.298381 0.411284 0.077 Uiso 1 1 calc GR . . . .
H00C H 0.622276 0.296026 0.369892 0.077 Uiso 1 1 calc GR . . . .
C00G C 0.83803(13) 0.4712(2) 0.8622(2) 0.0577(5) Uani 1 1 d . . . . .
H00G H 0.841965 0.533665 0.931528 0.069 Uiso 1 1 calc R . . . .
C00H C 0.82530(13) 0.2842(2) 0.6605(2) 0.0555(5) Uani 1 1 d . . . . .
H00H H 0.821514 0.219533 0.593203 0.067 Uiso 1 1 calc R . . . .
C00I C 0.21523(13) 0.3468(2) 0.5148(2) 0.0575(5) Uani 1 1 d . . . . .
H00I H 0.244945 0.321986 0.449757 0.069 Uiso 1 1 calc R . . . .
C00J C 0.90992(14) 0.3919(3) 0.8596(3) 0.0719(7) Uani 1 1 d . . . . .
H00J H 0.963093 0.401225 0.926027 0.086 Uiso 1 1 calc R . . . .
C00K C 0.90275(14) 0.2993(3) 0.7590(3) 0.0700(7) Uani 1 1 d . . . . .
H00K H 0.951496 0.245302 0.757153 0.084 Uiso 1 1 calc R . . . .
C00L C 0.21615(14) 0.4292(2) 0.7400(2) 0.0559(5) Uani 1 1 d . . . . .
C00M C 0.08006(15) 0.3804(3) 0.5854(3) 0.0765(7) Uani 1 1 d . . . . .
H00M H 0.018139 0.375542 0.562671 0.092 Uiso 1 1 calc R . . . .
C00N C 0.12618(15) 0.3427(3) 0.4876(3) 0.0730(7) Uani 1 1 d . . . . .
H00N H 0.093861 0.314241 0.402417 0.088 Uiso 1 1 calc R . . . .
C00O C 0.12207(15) 0.4225(3) 0.7081(3) 0.0718(7) Uani 1 1 d . . . . .
H00O H 0.090736 0.446922 0.771264 0.086 Uiso 1 1 calc R . . . .
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'
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
_geom_angle_publ_flag
C006 S001 C00D 98.73(8) . . ?
C00C O002 N00E 110.28(15) . . ?
C004 N003 C00A 119.28(14) . . ?
C004 N003 C00F 118.13(15) . . ?
C00A N003 C00F 117.33(15) . . ?
N003 C004 C006 119.81(15) . . ?
N003 C004 C009 122.54(16) . . ?
C009 C004 C006 117.65(16) . . ?
C007 C005 H005 119.4 . . ?
C009 C005 H005 119.4 . . ?
C009 C005 C007 121.13(17) . . ?
C004 C006 S001 119.52(13) . . ?
C008 C006 S001 119.32(13) . . ?
C008 C006 C004 121.03(16) . . ?
C005 C007 C008 118.23(16) . . ?
C005 C007 C00C 121.09(16) . . ?
C008 C007 C00C 120.68(17) . . ?
C006 C008 C007 120.90(17) . . ?
C006 C008 H008 119.6 . . ?
C007 C008 H008 119.6 . . ?
C004 C009 H009 119.5 . . ?
C005 C009 C004 120.98(17) . . ?
C005 C009 H009 119.5 . . ?
C00D C00A N003 119.85(16) . . ?
C00H C00A N003 121.82(18) . . ?
C00H C00A C00D 118.33(18) . . ?
C00C C00B C00I 136.04(19) . . ?
C00C C00B C00L 103.82(18) . . ?
C00I C00B C00L 120.10(18) . . ?
O002 C00C C007 116.43(16) . . ?
O002 C00C C00B 108.96(16) . . ?
C00B C00C C007 134.61(18) . . ?
C00A C00D S001 119.50(14) . . ?
C00G C00D S001 119.70(16) . . ?
C00G C00D C00A 120.76(18) . . ?
C00L N00E O002 103.94(17) . . ?
N003 C00F H00A 109.5 . . ?
N003 C00F H00B 109.5 . . ?
N003 C00F H00C 109.5 . . ?
H00A C00F H00B 109.5 . . ?
H00A C00F H00C 109.5 . . ?
H00B C00F H00C 109.5 . . ?
C00D C00G H00G 119.9 . . ?
C00D C00G C00J 120.1(2) . . ?
C00J C00G H00G 119.9 . . ?
C00A C00H H00H 119.9 . . ?
C00K C00H C00A 120.3(2) . . ?
C00K C00H H00H 119.9 . . ?
C00B C00I H00I 120.9 . . ?
C00N C00I C00B 118.2(2) . . ?
C00N C00I H00I 120.9 . . ?
C00G C00J H00J 120.3 . . ?
C00K C00J C00G 119.3(2) . . ?
C00K C00J H00J 120.3 . . ?
C00H C00K H00K 119.4 . . ?
C00J C00K C00H 121.2(2) . . ?
C00J C00K H00K 119.4 . . ?
C00B C00L C00O 120.2(2) . . ?
N00E C00L C00B 113.00(19) . . ?
N00E C00L C00O 126.8(2) . . ?
C00N C00M H00M 118.9 . . ?
C00O C00M H00M 118.9 . . ?
C00O C00M C00N 122.2(2) . . ?
C00I C00N C00M 121.6(2) . . ?
C00I C00N H00N 119.2 . . ?
C00M C00N H00N 119.2 . . ?
C00L C00O H00O 121.1 . . ?
C00M C00O C00L 117.8(2) . . ?
C00M C00O H00O 121.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C006 1.7599(18) . ?
S001 C00D 1.7596(19) . ?
O002 C00C 1.349(2) . ?
O002 N00E 1.414(2) . ?
N003 C004 1.398(2) . ?
N003 C00A 1.411(2) . ?
N003 C00F 1.461(2) . ?
C004 C006 1.403(2) . ?
C004 C009 1.400(2) . ?
C005 H005 0.9400 . ?
C005 C007 1.391(3) . ?
C005 C009 1.377(3) . ?
C006 C008 1.377(2) . ?
C007 C008 1.395(3) . ?
C007 C00C 1.459(3) . ?
C008 H008 0.9400 . ?
C009 H009 0.9400 . ?
C00A C00D 1.399(3) . ?
C00A C00H 1.392(3) . ?
C00B C00C 1.371(3) . ?
C00B C00I 1.413(3) . ?
C00B C00L 1.422(3) . ?
C00D C00G 1.382(3) . ?
N00E C00L 1.317(3) . ?
C00F H00A 0.9700 . ?
C00F H00B 0.9700 . ?
C00F H00C 0.9700 . ?
C00G H00G 0.9400 . ?
C00G C00J 1.384(3) . ?
C00H H00H 0.9400 . ?
C00H C00K 1.380(3) . ?
C00I H00I 0.9400 . ?
C00I C00N 1.352(3) . ?
C00J H00J 0.9400 . ?
C00J C00K 1.374(3) . ?
C00K H00K 0.9400 . ?
C00L C00O 1.428(3) . ?
C00M H00M 0.9400 . ?
C00M C00N 1.429(4) . ?
C00M C00O 1.338(4) . ?
C00N H00N 0.9400 . ?
C00O H00O 0.9400 . ?
