#------------------------------------------------------------------------------
#$Date: 2021-02-12 07:09:02 +0200 (Fri, 12 Feb 2021) $
#$Revision: 261910 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/22/7242260.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_7242260
loop_
_publ_author_name
'Custodio, Jean'
'd'Oliveira, Giulio Demetrius Creazo'
'Gotardo, Fernando'
'Cocca, Leandro'
'Boni, Leonardo De'
'Perez, Caridad'
'Napolitano, Hamilton'
'Osório, Francisco'
'Valverde, Clodoaldo'
_publ_section_title
;
 Second-order nonlinear optical properties of two chalcone derivatives:
 insights from sum-over-states
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D0CP06469F
_journal_year                    2021
_chemical_formula_moiety         'C21 H16 N2 O5 S'
_chemical_formula_sum            'C21 H16 N2 O5 S'
_chemical_formula_weight         408.42
_chemical_name_common            'Sulfonamide chalcone'
_chemical_name_systematic
(E)-3-(2-methoxyphenyl)-1-(2-(phenylsulfonylamine)phenyl)prop-2-en-1-one
_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   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc21xj8s
_audit_creation_date             2019-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-19 deposited with the CCDC.	2021-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.242(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0149(16)
_cell_length_b                   7.6562(9)
_cell_length_c                   18.380(2)
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.26
_cell_volume                     1934.3(4)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.950
_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  0.0470
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30977
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.829
_diffrn_reflns_theta_min         1.481
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.204
_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-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1361 before and 0.0592 after correction. The Ratio of minimum to maximum transmission is 0.8599. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.462
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3950
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0528
_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)+(0.0502P)²+0.7905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1193
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2976
_reflns_number_total             3950
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cp06469f2.cif
_cod_data_source_block           mo_g32_1_0m
_cod_original_cell_volume        1934.4(4)
_cod_database_code               7242260
_shelx_shelxl_version_number     2014/7
_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   0.981
_shelx_estimated_absorpt_t_min   0.912
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C16 \\sim C21 \\sim C20 \\sim C19 \\sim C18 \\sim C17: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
O4 \\sim S1 \\sim O5: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C7(H7), C8(H8), C14(H14), C13(H13), C12(H12), C4(H4),
 C17(H17), C21(H21), C18(H18), C20(H20), C19(H19)
;
_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
S1 S 0.31610(3) 0.19620(9) 0.14857(2) 0.05280(19) Uani 1 1 d . U . . .
O1 O 0.50851(10) 0.2684(3) 0.33653(8) 0.0774(6) Uani 1 1 d . . . . .
O2 O 0.97082(12) 0.5115(3) 0.68939(11) 0.1051(8) Uani 1 1 d . . . . .
O5 O 0.39704(10) 0.2487(3) 0.11688(8) 0.0789(6) Uani 1 1 d . U . . .
O3 O 0.94477(11) 0.5197(3) 0.57105(11) 0.0845(6) Uani 1 1 d . . . . .
N2 N 0.35547(11) 0.2128(3) 0.23723(8) 0.0599(5) Uani 1 1 d . . . . .
H2 H 0.4132 0.2546 0.2506 0.072 Uiso 1 1 calc R . . . .
N1 N 0.91853(12) 0.4908(3) 0.62902(11) 0.0627(5) Uani 1 1 d . . . . .
C2 C 0.81829(13) 0.4271(3) 0.62611(11) 0.0474(5) Uani 1 1 d . . . . .
C1 C 0.75894(13) 0.4051(3) 0.55750(10) 0.0442(5) Uani 1 1 d . . . . .
H1 H 0.7817 0.4315 0.5145 0.053 Uiso 1 1 calc R . . . .
C6 C 0.66458(13) 0.3431(3) 0.55325(10) 0.0417(4) Uani 1 1 d . . . . .
C7 C 0.60336(13) 0.3163(3) 0.47994(10) 0.0466(5) Uani 1 1 d . . . . .
H7 H 0.6312 0.3455 0.4396 0.056 Uiso 1 1 calc R . . . .
C8 C 0.51384(13) 0.2560(3) 0.46413(10) 0.0486(5) Uani 1 1 d . . . . .
H8 H 0.4824 0.2244 0.5023 0.058 Uiso 1 1 calc R . . . .
C9 C 0.46300(13) 0.2381(3) 0.38617(10) 0.0470(5) Uani 1 1 d . . . . .
C10 C 0.35922(12) 0.1836(3) 0.36874(9) 0.0396(4) Uani 1 1 d . . . . .
C15 C 0.30787(12) 0.1680(3) 0.29507(9) 0.0425(5) Uani 1 1 d . . . . .
C14 C 0.21151(13) 0.1114(3) 0.28101(10) 0.0517(5) Uani 1 1 d . . . . .
H14 H 0.1781 0.0990 0.2323 0.062 Uiso 1 1 calc R . . . .
C13 C 0.16546(14) 0.0738(3) 0.33904(11) 0.0548(6) Uani 1 1 d . . . . .
H13 H 0.1009 0.0373 0.3291 0.066 Uiso 1 1 calc R . . . .
C12 C 0.21385(14) 0.0898(3) 0.41136(11) 0.0557(6) Uani 1 1 d . . . . .
H12 H 0.1823 0.0647 0.4502 0.067 Uiso 1 1 calc R . . . .
C11 C 0.30950(14) 0.1431(3) 0.42577(10) 0.0485(5) Uani 1 1 d . . . . .
H11 H 0.3422(15) 0.152(3) 0.4767(12) 0.058 Uiso 1 1 d R . . . .
C5 C 0.63325(15) 0.3062(3) 0.61916(11) 0.0525(5) Uani 1 1 d . . . . .
H5 H 0.5700(17) 0.262(3) 0.6183(12) 0.063 Uiso 1 1 d R . . . .
C4 C 0.69435(16) 0.3296(4) 0.68682(12) 0.0673(7) Uani 1 1 d . . . . .
H4 H 0.6723 0.3039 0.7302 0.081 Uiso 1 1 calc R . . . .
C3 C 0.78816(16) 0.3908(4) 0.69106(12) 0.0622(6) Uani 1 1 d . . . . .
H3 H 0.8343(17) 0.408(3) 0.7384(13) 0.075 Uiso 1 1 d R . . . .
C16 C 0.22328(14) 0.3525(3) 0.12498(9) 0.0467(5) Uani 1 1 d . U . . .
C17 C 0.12758(14) 0.2970(3) 0.10536(12) 0.0556(6) Uani 1 1 d . U . . .
H17 H 0.1131 0.1784 0.1039 0.067 Uiso 1 1 calc R . . . .
C21 C 0.2454(2) 0.5280(4) 0.12535(11) 0.0686(7) Uani 1 1 d . U . . .
H21 H 0.3096 0.5657 0.1372 0.082 Uiso 1 1 calc R . . . .
C18 C 0.05424(18) 0.4178(4) 0.08802(14) 0.0760(8) Uani 1 1 d . U . . .
H18 H -0.0100 0.3808 0.0750 0.091 Uiso 1 1 calc R . . . .
C20 C 0.1693(3) 0.6478(4) 0.10747(14) 0.0850(9) Uani 1 1 d . U . . .
H20 H 0.1825 0.7669 0.1075 0.102 Uiso 1 1 calc R . . . .
C19 C 0.0752(2) 0.5898(5) 0.08989(16) 0.0860(9) Uani 1 1 d . U . . .
H19 H 0.0248 0.6705 0.0791 0.103 Uiso 1 1 calc R . . . .
O4 O 0.27246(11) 0.0286(2) 0.13122(8) 0.0662(4) Uani 1 1 d . 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_
_citation_id
_citation_doi
_citation_year
1 10.1007/s00044-019-02384-8 2019
2 10.1039/C9NJ05612B 2020
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
O5 S1 N2 104.24(8) . . ?
O5 S1 C16 108.40(11) . . ?
O5 S1 O4 120.00(11) . . ?
N2 S1 C16 106.56(9) . . ?
O4 S1 N2 109.97(10) . . ?
O4 S1 C16 106.97(10) . . ?
C15 N2 S1 128.59(13) . . ?
O2 N1 C2 118.4(2) . . ?
O3 N1 O2 123.09(19) . . ?
O3 N1 C2 118.49(18) . . ?
C1 C2 N1 118.23(18) . . ?
C3 C2 N1 119.18(18) . . ?
C3 C2 C1 122.58(18) . . ?
C2 C1 C6 119.33(17) . . ?
C1 C6 C7 118.62(16) . . ?
C1 C6 C5 118.44(17) . . ?
C5 C6 C7 122.92(17) . . ?
C8 C7 C6 127.97(18) . . ?
C7 C8 C9 120.39(17) . . ?
O1 C9 C8 118.64(17) . . ?
O1 C9 C10 121.25(16) . . ?
C8 C9 C10 120.11(16) . . ?
C15 C10 C9 121.72(15) . . ?
C11 C10 C9 120.59(16) . . ?
C11 C10 C15 117.69(16) . . ?
N2 C15 C10 118.56(15) . . ?
C14 C15 N2 121.47(16) . . ?
C14 C15 C10 119.96(16) . . ?
C13 C14 C15 120.24(17) . . ?
C12 C13 C14 120.79(17) . . ?
C13 C12 C11 119.37(17) . . ?
C12 C11 C10 121.94(18) . . ?
C4 C5 C6 120.81(19) . . ?
C5 C4 C3 120.8(2) . . ?
C2 C3 C4 118.07(19) . . ?
C17 C16 S1 119.16(18) . . ?
C21 C16 S1 120.47(18) . . ?
C21 C16 C17 120.4(2) . . ?
C18 C17 C16 119.8(2) . . ?
C16 C21 C20 118.6(2) . . ?
C19 C18 C17 120.2(3) . . ?
C19 C20 C21 119.9(3) . . ?
C18 C19 C20 121.2(3) . . ?
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 O5 1.4300(15) . ?
S1 N2 1.6205(16) . ?
S1 C16 1.759(2) . ?
S1 O4 1.4303(18) . ?
O1 C9 1.233(2) . ?
O2 N1 1.215(2) . ?
O3 N1 1.213(2) . ?
N2 C15 1.403(2) . ?
N1 C2 1.478(2) . ?
C2 C1 1.379(2) . ?
C2 C3 1.370(3) . ?
C1 C6 1.393(2) . ?
C6 C7 1.464(2) . ?
C6 C5 1.395(3) . ?
C7 C8 1.315(3) . ?
C8 C9 1.477(3) . ?
C9 C10 1.487(2) . ?
C10 C15 1.409(2) . ?
C10 C11 1.402(2) . ?
C15 C14 1.393(2) . ?
C14 C13 1.380(3) . ?
C13 C12 1.375(3) . ?
C12 C11 1.377(3) . ?
C5 C4 1.377(3) . ?
C4 C3 1.384(3) . ?
C16 C17 1.386(3) . ?
C16 C21 1.378(3) . ?
C17 C18 1.373(3) . ?
C21 C20 1.397(4) . ?
C18 C19 1.348(4) . ?
C20 C19 1.369(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.86 1.86 2.566(2) 138.0 .
C8 H8 O5 0.93 2.63 3.515(2) 160.3 4_566
C11 H11 O5 0.96(2) 2.65(2) 3.585(2) 163.6(17) 4_566
C5 H5 O5 0.95(2) 2.42(2) 3.329(2) 160.9(19) 4_566
C20 H20 O4 0.93 2.36 3.246(4) 158.5 1_565
C19 H19 O3 0.93 2.62 3.486(4) 156.0 4_475
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 N2 C15 C10 175.95(17) . . . . ?
S1 N2 C15 C14 -5.0(3) . . . . ?
S1 C16 C17 C18 178.91(17) . . . . ?
S1 C16 C21 C20 -178.93(16) . . . . ?
O1 C9 C10 C15 -1.5(3) . . . . ?
O1 C9 C10 C11 177.5(2) . . . . ?
O2 N1 C2 C1 179.5(2) . . . . ?
O2 N1 C2 C3 -1.1(3) . . . . ?
O5 S1 N2 C15 -176.0(2) . . . . ?
O5 S1 C16 C17 139.54(16) . . . . ?
O5 S1 C16 C21 -39.87(18) . . . . ?
O3 N1 C2 C1 -0.6(3) . . . . ?
O3 N1 C2 C3 178.8(2) . . . . ?
N2 S1 C16 C17 -108.78(16) . . . . ?
N2 S1 C16 C21 71.81(17) . . . . ?
N2 C15 C14 C13 -177.8(2) . . . . ?
N1 C2 C1 C6 179.15(19) . . . . ?
N1 C2 C3 C4 -179.3(2) . . . . ?
C2 C1 C6 C7 -178.47(19) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 C6 C7 C8 178.5(2) . . . . ?
C1 C6 C5 C4 -0.4(3) . . . . ?
C6 C7 C8 C9 179.9(2) . . . . ?
C6 C5 C4 C3 0.3(4) . . . . ?
C7 C6 C5 C4 178.4(2) . . . . ?
C7 C8 C9 O1 5.3(3) . . . . ?
C7 C8 C9 C10 -175.1(2) . . . . ?
C8 C9 C10 C15 178.9(2) . . . . ?
C8 C9 C10 C11 -2.1(3) . . . . ?
C9 C10 C15 N2 -2.8(3) . . . . ?
C9 C10 C15 C14 178.1(2) . . . . ?
C9 C10 C11 C12 -179.1(2) . . . . ?
C10 C15 C14 C13 1.3(3) . . . . ?
C15 C10 C11 C12 0.0(3) . . . . ?
C15 C14 C13 C12 -0.6(4) . . . . ?
C14 C13 C12 C11 -0.3(4) . . . . ?
C13 C12 C11 C10 0.6(4) . . . . ?
C11 C10 C15 N2 178.16(19) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C5 C4 C3 C2 -0.1(4) . . . . ?
C3 C2 C1 C6 -0.2(3) . . . . ?
C16 S1 N2 C15 69.5(2) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C16 C21 C20 C19 -0.2(4) . . . . ?
C17 C16 C21 C20 1.7(3) . . . . ?
C17 C18 C19 C20 1.3(4) . . . . ?
C21 C16 C17 C18 -1.7(3) . . . . ?
C21 C20 C19 C18 -1.3(4) . . . . ?
O4 S1 N2 C15 -46.1(2) . . . . ?
O4 S1 C16 C17 8.82(17) . . . . ?
O4 S1 C16 C21 -170.60(15) . . . . ?
