#------------------------------------------------------------------------------
#$Date: 2021-07-05 21:14:11 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267245 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158081.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_7158081
loop_
_publ_author_name
'Singha, Monisha'
'Bhattacharya, Prabuddha'
'Ray, Debashis'
'Basak, Amit'
_publ_section_title
;
 Sterically hindering the trajectory of nucleophilic attack towards
 p-benzynes by a properly oriented hydrogen atom: an approach to
 achieve regioselectivity.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5148
_journal_page_last               5154
_journal_paper_doi               10.1039/d1ob00521a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C24 H20 Cl N O2 S'
_chemical_formula_weight         421.92
_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_method           SHELXL-2017/1
_audit_update_record
;
2021-02-09 deposited with the CCDC.	2021-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.300(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0989(18)
_cell_length_b                   34.797(10)
_cell_length_c                   7.6810(18)
_cell_measurement_reflns_used    2147
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.352
_cell_measurement_theta_min      2.341
_cell_volume                     2066.7(9)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1011
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19645
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.352
_diffrn_reflns_theta_min         2.341
_exptl_absorpt_coefficient_mu    0.306
_exptl_crystal_colour            'PALE YELLOW'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             880
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1518
_refine_ls_R_factor_gt           0.0686
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.2188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2147
_reflns_number_total             4223
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00521a2.cif
_cod_data_source_block           ms_0m_a_a
_cod_depositor_comments
'Adding full bibliography for 7158079--7158081.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158081
_shelx_shelxl_version_number     2017/1
_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.
;
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 0.33691(18) 0.41398(3) 0.23223(17) 0.0610(4) Uani 1 1 d . . . . .
Cl02 Cl 0.05937(15) 0.27644(4) 0.28955(19) 0.0718(4) Uani 1 1 d . . . . .
O003 O 0.1827(5) 0.40833(9) 0.0836(5) 0.0750(10) Uani 1 1 d . . . . .
O004 O 0.4717(5) 0.43782(9) 0.2078(5) 0.0785(11) Uani 1 1 d . . . . .
N005 N 0.4194(5) 0.37150(9) 0.2901(5) 0.0501(9) Uani 1 1 d . . . . .
C006 C 0.3821(5) 0.30201(11) 0.3272(5) 0.0418(9) Uani 1 1 d . . . . .
C007 C 0.5933(5) 0.18851(12) 0.3639(5) 0.0456(10) Uani 1 1 d . . . . .
C008 C 0.5226(5) 0.22733(11) 0.3491(5) 0.0438(10) Uani 1 1 d . . . . .
C009 C 0.3428(5) 0.23198(11) 0.3238(5) 0.0457(10) Uani 1 1 d . . . . .
C00A C 0.2797(5) 0.26998(12) 0.3156(5) 0.0453(10) Uani 1 1 d . . . . .
C00B C 0.5597(5) 0.29693(11) 0.3531(5) 0.0446(10) Uani 1 1 d . . . . .
C00C C 0.6258(5) 0.26036(12) 0.3640(6) 0.0490(10) Uani 1 1 d . . . . .
H00C H 0.743765 0.257322 0.381970 0.059 Uiso 1 1 calc R U . . .
C00D C 0.2351(6) 0.19878(13) 0.3108(6) 0.0547(11) Uani 1 1 d . . . . .
H00D H 0.116729 0.201898 0.289682 0.066 Uiso 1 1 calc R U . . .
C00E C 0.4826(6) 0.15679(12) 0.3582(6) 0.0520(11) Uani 1 1 d . . . . .
C00F C 0.7699(6) 0.18099(14) 0.3863(6) 0.0604(12) Uani 1 1 d . . . . .
H00F H 0.843507 0.201370 0.383948 0.073 Uiso 1 1 calc R U . . .
C00G C 0.6756(6) 0.33162(12) 0.3685(6) 0.0549(11) Uani 1 1 d . . . . .
H00A H 0.784384 0.326768 0.461643 0.066 Uiso 1 1 calc R U . . .
H00B H 0.700450 0.335287 0.253645 0.066 Uiso 1 1 calc R U . . .
C00H C 0.3022(6) 0.34159(12) 0.3173(6) 0.0545(11) Uani 1 1 d . . . . .
H00E H 0.195632 0.342331 0.217361 0.065 Uiso 1 1 calc R U . . .
H00G H 0.274095 0.346662 0.429328 0.065 Uiso 1 1 calc R U . . .
C00I C 0.3032(6) 0.16292(13) 0.3289(6) 0.0568(12) Uani 1 1 d . . . . .
H00I H 0.230801 0.141866 0.321892 0.068 Uiso 1 1 calc R U . . .
C00J C 0.5965(6) 0.36805(13) 0.4159(6) 0.0597(12) Uani 1 1 d . . . . .
H00H H 0.593113 0.366957 0.540941 0.072 Uiso 1 1 calc R U . . .
H00J H 0.665059 0.390142 0.403187 0.072 Uiso 1 1 calc R U . . .
C00K C 0.5546(7) 0.11931(13) 0.3853(6) 0.0624(13) Uani 1 1 d . . . . .
H00K H 0.482917 0.098392 0.384476 0.075 Uiso 1 1 calc R U . . .
C00L C 0.8351(7) 0.14459(15) 0.4114(7) 0.0693(14) Uani 1 1 d . . . . .
H00L H 0.952239 0.140470 0.427895 0.083 Uiso 1 1 calc R U . . .
C00M C 0.2741(7) 0.43322(13) 0.4153(7) 0.0650(13) Uani 1 1 d . . . . .
C00N C 0.7259(8) 0.11336(15) 0.4125(7) 0.0707(14) Uani 1 1 d . . . . .
H00N H 0.770937 0.088601 0.431716 0.085 Uiso 1 1 calc R U . . .
C00O C 0.3805(8) 0.45720(13) 0.5390(7) 0.0799(16) Uani 1 1 d . . . . .
H00O H 0.491426 0.462218 0.532960 0.096 Uiso 1 1 calc R U . . .
C00P C 0.1602(13) 0.46700(19) 0.6859(10) 0.110(3) Uani 1 1 d . . . . .
C00Q C 0.1102(9) 0.42545(16) 0.4287(9) 0.0914(18) Uani 1 1 d . . . . .
H00Q H 0.036197 0.409013 0.345795 0.110 Uiso 1 1 calc R U . . .
C00R C 0.3234(11) 0.47409(16) 0.6736(8) 0.101(2) Uani 1 1 d . . . . .
H00R H 0.396666 0.490532 0.757218 0.122 Uiso 1 1 calc R U . . .
C00S C 0.0580(11) 0.4423(2) 0.5660(11) 0.113(3) Uani 1 1 d . . . . .
H00S H -0.050837 0.436480 0.576278 0.136 Uiso 1 1 calc R U . . .
C00T C 0.0972(12) 0.4874(2) 0.8314(9) 0.165(4) Uani 1 1 d . . . . .
H00M H 0.052566 0.468713 0.897779 0.248 Uiso 1 1 calc R U . . .
H00P H 0.007566 0.505318 0.773650 0.248 Uiso 1 1 calc R U . . .
H00T H 0.191914 0.500868 0.913964 0.248 Uiso 1 1 calc R U . . .
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'
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'
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
O003 S001 O004 119.6(2) . . ?
O003 S001 N005 106.42(19) . . ?
O004 S001 N005 107.2(2) . . ?
O003 S001 C00M 107.3(3) . . ?
O004 S001 C00M 107.3(2) . . ?
N005 S001 C00M 108.6(2) . . ?
C00H N005 C00J 113.2(3) . . ?
C00H N005 S001 116.9(3) . . ?
C00J N005 S001 119.5(3) . . ?
C00A C006 C00B 118.7(4) . . ?
C00A C006 C00H 119.5(4) . . ?
C00B C006 C00H 121.8(4) . . ?
C00E C007 C00F 117.9(4) . . ?
C00E C007 C008 119.3(4) . . ?
C00F C007 C008 122.7(4) . . ?
C00C C008 C009 118.6(4) . . ?
C00C C008 C007 122.8(4) . . ?
C009 C008 C007 118.6(4) . . ?
C00A C009 C008 117.1(4) . . ?
C00A C009 C00D 123.1(4) . . ?
C008 C009 C00D 119.7(4) . . ?
C006 C00A C009 123.5(4) . . ?
C006 C00A Cl02 118.6(3) . . ?
C009 C00A Cl02 118.0(3) . . ?
C00C C00B C006 119.3(4) . . ?
C00C C00B C00G 120.9(4) . . ?
C006 C00B C00G 119.8(4) . . ?
C00B C00C C008 122.8(4) . . ?
C00B C00C H00C 118.6 . . ?
C008 C00C H00C 118.6 . . ?
C00I C00D C009 121.0(4) . . ?
C00I C00D H00D 119.5 . . ?
C009 C00D H00D 119.5 . . ?
C007 C00E C00K 118.9(4) . . ?
C007 C00E C00I 119.8(4) . . ?
C00K C00E C00I 121.3(4) . . ?
C00L C00F C007 121.6(5) . . ?
C00L C00F H00F 119.2 . . ?
C007 C00F H00F 119.2 . . ?
C00J C00G C00B 113.0(4) . . ?
C00J C00G H00A 109.0 . . ?
C00B C00G H00A 109.0 . . ?
C00J C00G H00B 109.0 . . ?
C00B C00G H00B 109.0 . . ?
H00A C00G H00B 107.8 . . ?
N005 C00H C006 111.6(3) . . ?
N005 C00H H00E 109.3 . . ?
C006 C00H H00E 109.3 . . ?
N005 C00H H00G 109.3 . . ?
C006 C00H H00G 109.3 . . ?
H00E C00H H00G 108.0 . . ?
C00D C00I C00E 121.4(4) . . ?
C00D C00I H00I 119.3 . . ?
C00E C00I H00I 119.3 . . ?
N005 C00J C00G 108.0(3) . . ?
N005 C00J H00H 110.1 . . ?
C00G C00J H00H 110.1 . . ?
N005 C00J H00J 110.1 . . ?
C00G C00J H00J 110.1 . . ?
H00H C00J H00J 108.4 . . ?
C00N C00K C00E 121.4(5) . . ?
C00N C00K H00K 119.3 . . ?
C00E C00K H00K 119.3 . . ?
C00F C00L C00N 120.1(5) . . ?
C00F C00L H00L 119.9 . . ?
C00N C00L H00L 119.9 . . ?
C00Q C00M C00O 119.2(5) . . ?
C00Q C00M S001 119.6(4) . . ?
C00O C00M S001 121.1(4) . . ?
C00K C00N C00L 119.9(5) . . ?
C00K C00N H00N 120.0 . . ?
C00L C00N H00N 120.0 . . ?
C00M C00O C00R 120.0(6) . . ?
C00M C00O H00O 120.0 . . ?
C00R C00O H00O 120.0 . . ?
C00R C00P C00S 118.4(6) . . ?
C00R C00P C00T 120.1(9) . . ?
C00S C00P C00T 121.5(9) . . ?
C00M C00Q C00S 119.4(7) . . ?
C00M C00Q H00Q 120.3 . . ?
C00S C00Q H00Q 120.3 . . ?
C00P C00R C00O 121.1(7) . . ?
C00P C00R H00R 119.4 . . ?
C00O C00R H00R 119.5 . . ?
C00P C00S C00Q 121.8(7) . . ?
C00P C00S H00S 119.1 . . ?
C00Q C00S H00S 119.1 . . ?
C00P C00T H00M 109.6 . . ?
C00P C00T H00P 109.5 . . ?
H00M C00T H00P 109.4 . . ?
C00P C00T H00T 109.4 . . ?
H00M C00T H00T 109.4 . . ?
H00P C00T H00T 109.4 . . ?
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 O003 1.433(3) . ?
S001 O004 1.427(3) . ?
S001 N005 1.628(4) . ?
S001 C00M 1.764(5) . ?
Cl02 C00A 1.750(4) . ?
N005 C00H 1.465(5) . ?
N005 C00J 1.476(6) . ?
C006 C00A 1.377(5) . ?
C006 C00B 1.403(5) . ?
C006 C00H 1.514(5) . ?
C007 C00E 1.415(6) . ?
C007 C00F 1.413(6) . ?
C007 C008 1.458(5) . ?
C008 C00C 1.405(5) . ?
C008 C009 1.420(5) . ?
C009 C00A 1.413(5) . ?
C009 C00D 1.433(6) . ?
C00B C00C 1.373(5) . ?
C00B C00G 1.512(5) . ?
C00C H00C 0.9300 . ?
C00D C00I 1.355(6) . ?
C00D H00D 0.9300 . ?
C00E C00K 1.418(6) . ?
C00E C00I 1.418(6) . ?
C00F C00L 1.364(6) . ?
C00F H00F 0.9300 . ?
C00G C00J 1.513(6) . ?
C00G H00A 0.9700 . ?
C00G H00B 0.9700 . ?
C00H H00E 0.9700 . ?
C00H H00G 0.9700 . ?
C00I H00I 0.9300 . ?
C00J H00H 0.9700 . ?
C00J H00J 0.9700 . ?
C00K C00N 1.356(7) . ?
C00K H00K 0.9300 . ?
C00L C00N 1.403(7) . ?
C00L H00L 0.9300 . ?
C00M C00Q 1.389(7) . ?
C00M C00O 1.361(7) . ?
C00N H00N 0.9300 . ?
C00O C00R 1.383(8) . ?
C00O H00O 0.9300 . ?
C00P C00R 1.375(9) . ?
C00P C00S 1.348(10) . ?
C00P C00T 1.534(9) . ?
C00Q C00S 1.378(9) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?
C00T H00M 0.9603 . ?
C00T H00P 0.9603 . ?
C00T H00T 0.9603 . ?
