#------------------------------------------------------------------------------
#$Date: 2024-10-01 03:40:02 +0300 (Tue, 01 Oct 2024) $
#$Revision: 294947 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160158.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_7160158
loop_
_publ_author_name
'Joshi, Rajat'
'Rajput, Shruti'
'Grover, Nitika'
'Jain, Nidhi'
_publ_section_title
;
 Photocatalyst-free regioselective sulfonamidation of
 N-(2-hydroxyaryl)amides in visible-light
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D4OB01393J
_journal_year                    2024
_chemical_formula_moiety         'C15 H16 N2 O4 S'
_chemical_formula_sum            'C15 H16 N2 O4 S'
_chemical_formula_weight         320.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-06-03
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-07-12 deposited with the CCDC.	2024-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                84.04(3)
_cell_angle_beta                 75.55(3)
_cell_angle_gamma                76.36(3)
_cell_formula_units_Z            2
_cell_length_a                   7.453(4)
_cell_length_b                   10.846(5)
_cell_length_c                   11.701(6)
_cell_measurement_reflns_used    4809
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.58
_cell_volume                     889.1(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0680
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21802
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         1.799
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1255 before and 0.0736 after correction.
The Ratio of minimum to maximum transmission is 0.7468.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.014
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.970
_refine_diff_density_min         -0.852
_refine_diff_density_rms         0.277
_refine_ls_extinction_coef       0.49(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.316
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.316
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0972
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2816
_refine_ls_wR_factor_ref         0.3037
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2500
_reflns_number_total             3112
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01393j2.cif
_cod_data_source_block           rajat_nts_0m_a
_cod_original_cell_volume        889.1(7)
_cod_database_code               7160158
_shelx_shelxl_version_number     2019/1
_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.
;
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.997
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 58 electrons were 
found in a volume of 182Å³ in 1 void per unit cell. 
This is consistent with the presence of 
0.5[CHCl3] per Asymmetric Unit 
which account for 58 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 0.22479(12) 0.10630(8) 0.12379(8) 0.0425(5) Uani 1 1 d . . . . .
O002 O 0.2562(4) -0.0014(3) 0.0534(3) 0.0525(8) Uani 1 1 d . . . . .
O003 O 0.5423(4) 0.6140(2) 0.1946(3) 0.0519(8) Uani 1 1 d . . . . .
H003 H 0.656486 0.606868 0.187426 0.078 Uiso 1 1 calc R U . . .
O004 O 0.0495(4) 0.1978(3) 0.1390(3) 0.0556(8) Uani 1 1 d . . . . .
N1 N 0.3963(4) 0.1771(3) 0.0596(3) 0.0448(8) Uani 1 1 d . . . . .
H1 H 0.472865 0.146946 -0.004137 0.054 Uiso 1 1 calc R U . . .
N006 N 0.2012(4) 0.6270(3) 0.1644(3) 0.0453(9) Uani 1 1 d . . . . .
H006 H 0.247(7) 0.688(4) 0.167(4) 0.054 Uiso 1 1 d . U . . .
O007 O -0.0789(4) 0.5779(3) 0.1704(4) 0.0751(11) Uani 1 1 d . . . . .
C2 C 0.2867(5) 0.3988(3) 0.1181(3) 0.0417(9) Uani 1 1 d . . . . .
H2 H 0.167490 0.400930 0.105655 0.050 Uiso 1 1 calc R U . . .
C3 C 0.4265(5) 0.2882(3) 0.1045(3) 0.0367(8) Uani 1 1 d . . . . .
C4 C 0.3283(5) 0.5074(3) 0.1510(3) 0.0376(9) Uani 1 1 d . . . . .
C5 C 0.2548(5) 0.0476(3) 0.2639(4) 0.0444(9) Uani 1 1 d . . . . .
C6 C 0.5101(5) 0.5040(3) 0.1672(3) 0.0417(9) Uani 1 1 d . . . . .
C7 C 0.6022(5) 0.2828(3) 0.1230(3) 0.0418(9) Uani 1 1 d . . . . .
H7 H 0.692874 0.206874 0.114868 0.050 Uiso 1 1 calc R U . . .
C8 C 0.6454(5) 0.3913(3) 0.1540(4) 0.0461(10) Uani 1 1 d . . . . .
H8 H 0.765335 0.387816 0.165950 0.055 Uiso 1 1 calc R U . . .
C9 C -0.0777(6) 0.7945(4) 0.1823(5) 0.0640(13) Uani 1 1 d . . . . .
H9A H -0.145258 0.810095 0.262586 0.096 Uiso 1 1 calc R U . . .
H9B H -0.164673 0.818575 0.131496 0.096 Uiso 1 1 calc R U . . .
H9C H 0.018453 0.843412 0.159488 0.096 Uiso 1 1 calc R U . . .
C10 C 0.0124(5) 0.6573(3) 0.1720(3) 0.0447(9) Uani 1 1 d . . . . .
C11 C 0.3561(6) -0.0748(4) 0.2810(4) 0.0558(11) Uani 1 1 d . . . . .
H11 H 0.413109 -0.125795 0.216910 0.067 Uiso 1 1 calc R U . . .
C12 C 0.1764(6) 0.1245(4) 0.3610(4) 0.0574(11) Uani 1 1 d . . . . .
H12 H 0.112174 0.208022 0.350678 0.069 Uiso 1 1 calc R U . . .
C13 C 0.1949(7) 0.0762(5) 0.4701(4) 0.0675(13) Uani 1 1 d . . . . .
H13 H 0.140199 0.128029 0.533816 0.081 Uiso 1 1 calc R U . . .
C14 C 0.2914(7) -0.0469(5) 0.4914(4) 0.0616(12) Uani 1 1 d . . . . .
C15 C 0.3720(7) -0.1201(5) 0.3915(5) 0.0694(13) Uani 1 1 d . . . . .
H15 H 0.438907 -0.202959 0.401491 0.083 Uiso 1 1 calc R U . . .
C16 C 0.3085(9) -0.0997(6) 0.6126(5) 0.0845(17) Uani 1 1 d . . . . .
H16A H 0.285878 -0.031164 0.663716 0.127 Uiso 1 1 calc R U . . .
H16B H 0.433876 -0.150753 0.608714 0.127 Uiso 1 1 calc R U . . .
H16C H 0.216759 -0.151035 0.643053 0.127 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'
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
O002 S1 N1 104.08(17) . . ?
O002 S1 C5 107.31(18) . . ?
O004 S1 O002 119.91(18) . . ?
O004 S1 N1 108.64(17) . . ?
O004 S1 C5 107.56(18) . . ?
N1 S1 C5 108.98(17) . . ?
C6 O003 H003 109.5 . . ?
S1 N1 H1 118.3 . . ?
C3 N1 S1 123.4(2) . . ?
C3 N1 H1 118.3 . . ?
C4 N006 H006 116(3) . . ?
C10 N006 H006 114(3) . . ?
C10 N006 C4 129.4(3) . . ?
C3 C2 H2 120.7 . . ?
C3 C2 C4 118.6(3) . . ?
C4 C2 H2 120.7 . . ?
C2 C3 N1 120.6(3) . . ?
C7 C3 N1 117.5(3) . . ?
C7 C3 C2 121.7(3) . . ?
C2 C4 N006 124.5(3) . . ?
C2 C4 C6 120.2(3) . . ?
C6 C4 N006 115.2(3) . . ?
C11 C5 S1 120.8(3) . . ?
C11 C5 C12 119.1(4) . . ?
C12 C5 S1 120.1(3) . . ?
O003 C6 C4 116.9(3) . . ?
O003 C6 C8 123.7(3) . . ?
C8 C6 C4 119.4(3) . . ?
C3 C7 H7 120.0 . . ?
C3 C7 C8 119.9(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C8 C7 120.1(3) . . ?
C6 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
N006 C10 C9 115.4(3) . . ?
O007 C10 N006 122.6(3) . . ?
O007 C10 C9 122.0(4) . . ?
C5 C11 H11 120.1 . . ?
C15 C11 C5 119.9(4) . . ?
C15 C11 H11 120.1 . . ?
C5 C12 H12 120.3 . . ?
C13 C12 C5 119.4(4) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 118.4 . . ?
C12 C13 C14 123.2(4) . . ?
C14 C13 H13 118.4 . . ?
C13 C14 C15 115.7(4) . . ?
C13 C14 C16 122.7(5) . . ?
C15 C14 C16 121.6(5) . . ?
C11 C15 C14 122.6(4) . . ?
C11 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
S1 O002 1.440(3) . ?
S1 O004 1.426(3) . ?
S1 N1 1.628(3) . ?
S1 C5 1.744(4) . ?
O003 H003 0.8200 . ?
O003 C6 1.355(4) . ?
N1 H1 0.8600 . ?
N1 C3 1.448(4) . ?
N006 H006 0.82(5) . ?
N006 C4 1.412(5) . ?
N006 C10 1.350(5) . ?
O007 C10 1.221(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(5) . ?
C2 C4 1.399(5) . ?
C3 C7 1.367(5) . ?
C4 C6 1.406(5) . ?
C5 C11 1.386(5) . ?
C5 C12 1.402(6) . ?
C6 C8 1.384(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.395(5) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 C10 1.484(5) . ?
C11 H11 0.9300 . ?
C11 C15 1.359(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.356(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(7) . ?
C14 C15 1.406(7) . ?
C14 C16 1.497(6) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C3 C2 -59.5(4) . . . . ?
S1 N1 C3 C7 125.9(3) . . . . ?
S1 C5 C11 C15 -177.7(3) . . . . ?
S1 C5 C12 C13 177.6(3) . . . . ?
O002 S1 N1 C3 -176.9(3) . . . . ?
O002 S1 C5 C11 20.6(4) . . . . ?
O002 S1 C5 C12 -159.6(3) . . . . ?
O003 C6 C8 C7 -178.5(3) . . . . ?
O004 S1 N1 C3 54.3(3) . . . . ?
O004 S1 C5 C11 150.8(3) . . . . ?
O004 S1 C5 C12 -29.3(4) . . . . ?
N1 S1 C5 C11 -91.6(4) . . . . ?
N1 S1 C5 C12 88.3(4) . . . . ?
N1 C3 C7 C8 173.2(3) . . . . ?
N006 C4 C6 O003 0.6(5) . . . . ?
N006 C4 C6 C8 -179.0(3) . . . . ?
C2 C3 C7 C8 -1.4(5) . . . . ?
C2 C4 C6 O003 177.5(3) . . . . ?
C2 C4 C6 C8 -2.1(5) . . . . ?
C3 C2 C4 N006 178.0(3) . . . . ?
C3 C2 C4 C6 1.3(5) . . . . ?
C3 C7 C8 C6 0.6(6) . . . . ?
C4 N006 C10 O007 1.7(7) . . . . ?
C4 N006 C10 C9 -178.3(4) . . . . ?
C4 C2 C3 N1 -174.0(3) . . . . ?
C4 C2 C3 C7 0.4(5) . . . . ?
C4 C6 C8 C7 1.1(6) . . . . ?
C5 S1 N1 C3 -62.6(3) . . . . ?
C5 C11 C15 C14 -1.0(7) . . . . ?
C5 C12 C13 C14 1.1(7) . . . . ?
C10 N006 C4 C2 14.1(6) . . . . ?
C10 N006 C4 C6 -169.1(4) . . . . ?
C11 C5 C12 C13 -2.5(6) . . . . ?
C12 C5 C11 C15 2.5(6) . . . . ?
C12 C13 C14 C15 0.4(7) . . . . ?
C12 C13 C14 C16 -179.1(4) . . . . ?
C13 C14 C15 C11 -0.5(7) . . . . ?
C16 C14 C15 C11 179.1(4) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.062 0.500 0.500 182.2 57.8 '1 CHCl3'
