#------------------------------------------------------------------------------
#$Date: 2023-05-06 13:48:08 +0300 (Sat, 06 May 2023) $
#$Revision: 283593 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/42/2244233.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2244233
loop_
_publ_author_name
'Okmanov, Rasul Ya'
'Olimova, Manzura I.'
'Karabaeva, Surayyo B.'
'Sapaev, Frunza A.'
'Abdireymov, Kudaybergen B.'
_publ_section_title
;
 Syntheses, crystal structures and Hirshfeld surface analyses of
 N-aryl-sulfonyl derivatives of cytisine.
;
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              313
_journal_page_last               318
_journal_paper_doi               10.1107/S2056989023001950
_journal_volume                  79
_journal_year                    2023
_chemical_absolute_configuration rm
_chemical_formula_iupac          'C17 H17 Cl N2 O3 S'
_chemical_formula_moiety         'C17 H17 Cl N2 O3 S'
_chemical_formula_sum            'C17 H17 Cl N2 O3 S'
_chemical_formula_weight         364.83
_chemical_name_common
;
(7R,9R)-N-[(4-chlorophenyl)sulfonyl]cytisine
;
_chemical_name_systematic
(1R,5R)-3-[(4-chlorophenyl)sulfonyl]-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1374(14)
_cell_length_b                   11.448(2)
_cell_length_c                   20.844(4)
_cell_measurement_reflns_used    12750
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      71.2140
_cell_measurement_theta_min      3.8740
_cell_volume                     1703.1(6)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2020)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2015), PLATON (Spek, 2020) and publCIF
(Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS7    (Sheldrick, 2008)
;
_diffrn_ambient_temperature      299(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16028
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.422
_diffrn_reflns_theta_min         4.242
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       prizmatic
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.329
_refine_ls_abs_structure_details
;
Flack x determined using 1318 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -0.004(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0296
_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)+(0.0503P)²+0.1799P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                3203
_reflns_number_total             3289
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5674sup1.cif
_cod_data_source_block           II
_cod_depositor_comments
'Adding full bibliography for 2244232--2244234.cif.'
_cod_original_cell_volume        1703.2(6)
_cod_database_code               2244233
_cod_database_fobs_code          2244233
_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.22478(8) 0.27207(5) 0.34739(3) 0.03902(15) Uani d 1 . .
Cl Cl1 -0.32153(13) 0.49086(7) 0.54785(3) 0.0699(2) Uani d 1 . .
O O1 0.7771(3) 0.28000(19) 0.15317(11) 0.0647(5) Uani d 1 . .
O O2 0.1269(3) 0.18068(15) 0.31475(8) 0.0502(4) Uani d 1 . .
O O3 0.3999(3) 0.24823(16) 0.37824(9) 0.0524(4) Uani d 1 . .
N N1 0.4944(3) 0.36786(17) 0.16841(9) 0.0409(4) Uani d 1 . .
N N12 0.2648(3) 0.37419(16) 0.29491(8) 0.0401(4) Uani d 1 . .
C C2 0.6102(4) 0.2880(2) 0.13668(12) 0.0488(6) Uani d 1 . .
C C3 0.5244(5) 0.2229(3) 0.08706(15) 0.0627(7) Uani d 1 . .
H H3A 0.596685 0.171265 0.063104 0.075 Uiso calc 1 . .
C C4 0.3400(5) 0.2340(3) 0.07356(14) 0.0655(8) Uani d 1 . .
H H4A 0.287153 0.189194 0.041014 0.079 Uiso calc 1 . .
C C5 0.2283(4) 0.3117(3) 0.10791(13) 0.0562(6) Uani d 1 . .
H H5A 0.100971 0.317377 0.098975 0.067 Uiso calc 1 . .
C C6 0.3060(3) 0.3793(2) 0.15466(11) 0.0423(5) Uani d 1 . .
C C7 0.1922(3) 0.4659(2) 0.19194(12) 0.0451(5) Uani d 1 . .
H H7A 0.088762 0.492844 0.164794 0.054 Uiso calc 1 . .
C C8 0.3121(4) 0.5714(2) 0.21021(14) 0.0529(6) Uani d 1 . .
H H8A 0.363572 0.607885 0.172078 0.064 Uiso calc 1 . .
H H8B 0.237218 0.628713 0.232979 0.064 Uiso calc 1 . .
C C9 0.4687(4) 0.5263(2) 0.25296(13) 0.0476(5) Uani d 1 . .
H H9A 0.546300 0.592999 0.265695 0.057 Uiso calc 1 . .
C C10 0.5921(3) 0.4407(2) 0.21691(13) 0.0471(6) Uani d 1 . .
H H10A 0.690567 0.484286 0.195534 0.057 Uiso calc 1 . .
H H10B 0.651477 0.389329 0.247811 0.057 Uiso calc 1 . .
C C11 0.3847(4) 0.4731(2) 0.31352(12) 0.0480(6) Uani d 1 . .
H H11A 0.483789 0.446415 0.341787 0.058 Uiso calc 1 . .
H H11B 0.311175 0.531235 0.336171 0.058 Uiso calc 1 . .
C C13 0.1095(3) 0.4089(2) 0.25235(12) 0.0451(5) Uani d 1 . .
H H13A 0.027946 0.463659 0.274269 0.054 Uiso calc 1 . .
H H13B 0.036134 0.340816 0.240581 0.054 Uiso calc 1 . .
C C1' 0.0721(3) 0.3307(2) 0.40561(11) 0.0395(5) Uani d 1 . .
C C2' 0.1424(4) 0.4029(3) 0.45401(13) 0.0536(6) Uani d 1 . .
H H2'A 0.270287 0.417502 0.456776 0.064 Uiso calc 1 . .
C C3' 0.0214(5) 0.4522(3) 0.49743(13) 0.0607(7) Uani d 1 . .
H H3'A 0.066574 0.501348 0.529405 0.073 Uiso calc 1 . .
C C4' -0.1678(4) 0.4284(2) 0.49336(11) 0.0472(6) Uani d 1 . .
C C5' -0.2378(4) 0.3554(3) 0.44671(12) 0.0549(6) Uani d 1 . .
H H5'A -0.365241 0.338706 0.445122 0.066 Uiso calc 1 . .
C C6' -0.1173(4) 0.3073(2) 0.40242(12) 0.0496(6) Uani d 1 . .
H H6'A -0.163668 0.259030 0.370264 0.060 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
O2 S1 O3 . . 120.05(11) ?
O2 S1 N12 . . 106.96(10) ?
O3 S1 N12 . . 106.62(11) ?
O2 S1 C1' . . 107.67(11) ?
O3 S1 C1' . . 107.63(11) ?
N12 S1 C1' . . 107.33(11) ?
C6 N1 C2 . . 122.6(2) ?
C6 N1 C10 . . 123.0(2) ?
C2 N1 C10 . . 114.32(19) ?
C11 N12 C13 . . 112.9(2) ?
C11 N12 S1 . . 118.55(15) ?
C13 N12 S1 . . 117.80(16) ?
O1 C2 N1 . . 118.9(3) ?
O1 C2 C3 . . 125.4(3) ?
N1 C2 C3 . . 115.7(2) ?
C4 C3 C2 . . 121.6(3) ?
C4 C3 H3A . . 119.2 ?
C2 C3 H3A . . 119.2 ?
C3 C4 C5 . . 120.7(3) ?
C3 C4 H4A . . 119.7 ?
C5 C4 H4A . . 119.7 ?
C6 C5 C4 . . 119.9(3) ?
C6 C5 H5A . . 120.1 ?
C4 C5 H5A . . 120.1 ?
C5 C6 N1 . . 119.4(2) ?
C5 C6 C7 . . 121.7(2) ?
N1 C6 C7 . . 118.9(2) ?
C6 C7 C8 . . 110.4(2) ?
C6 C7 C13 . . 110.61(19) ?
C8 C7 C13 . . 110.3(2) ?
C6 C7 H7A . . 108.5 ?
C8 C7 H7A . . 108.5 ?
C13 C7 H7A . . 108.5 ?
C9 C8 C7 . . 106.80(19) ?
C9 C8 H8A . . 110.4 ?
C7 C8 H8A . . 110.4 ?
C9 C8 H8B . . 110.4 ?
C7 C8 H8B . . 110.4 ?
H8A C8 H8B . . 108.6 ?
C10 C9 C8 . . 110.9(2) ?
C10 C9 C11 . . 112.4(2) ?
C8 C9 C11 . . 109.4(2) ?
C10 C9 H9A . . 108.0 ?
C8 C9 H9A . . 108.0 ?
C11 C9 H9A . . 108.0 ?
N1 C10 C9 . . 115.3(2) ?
N1 C10 H10A . . 108.4 ?
C9 C10 H10A . . 108.4 ?
N1 C10 H10B . . 108.4 ?
C9 C10 H10B . . 108.4 ?
H10A C10 H10B . . 107.5 ?
N12 C11 C9 . . 108.5(2) ?
N12 C11 H11A . . 110.0 ?
C9 C11 H11A . . 110.0 ?
N12 C11 H11B . . 110.0 ?
C9 C11 H11B . . 110.0 ?
H11A C11 H11B . . 108.4 ?
N12 C13 C7 . . 108.57(19) ?
N12 C13 H13A . . 110.0 ?
C7 C13 H13A . . 110.0 ?
N12 C13 H13B . . 110.0 ?
C7 C13 H13B . . 110.0 ?
H13A C13 H13B . . 108.4 ?
C6' C1' C2' . . 120.1(2) ?
C6' C1' S1 . . 119.92(18) ?
C2' C1' S1 . . 120.00(19) ?
C3' C2' C1' . . 119.6(2) ?
C3' C2' H2'A . . 120.2 ?
C1' C2' H2'A . . 120.2 ?
C2' C3' C4' . . 119.6(2) ?
C2' C3' H3'A . . 120.2 ?
C4' C3' H3'A . . 120.2 ?
C5' C4' C3' . . 121.2(2) ?
C5' C4' Cl1 . . 118.9(2) ?
C3' C4' Cl1 . . 119.8(2) ?
C4' C5' C6' . . 119.3(2) ?
C4' C5' H5'A . . 120.3 ?
C6' C5' H5'A . . 120.3 ?
C5' C6' C1' . . 120.2(2) ?
C5' C6' H6'A . . 119.9 ?
C1' C6' H6'A . . 119.9 ?
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
S1 O2 . 1.4304(17) ?
S1 O3 . 1.4319(18) ?
S1 N12 . 1.6262(19) ?
S1 C1' . 1.764(2) ?
Cl1 C4' . 1.733(3) ?
O1 C2 . 1.243(3) ?
N1 C6 . 1.381(3) ?
N1 C2 . 1.399(3) ?
N1 C10 . 1.485(3) ?
N12 C11 . 1.471(3) ?
N12 C13 . 1.474(3) ?
C2 C3 . 1.414(4) ?
C3 C4 . 1.352(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.393(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.363(4) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.499(3) ?
C7 C8 . 1.528(4) ?
C7 C13 . 1.537(3) ?
C7 H7A . 0.9800 ?
C8 C9 . 1.520(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.517(4) ?
C9 C11 . 1.524(4) ?
C9 H9A . 0.9800 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C1' C6' . 1.379(3) ?
C1' C2' . 1.398(3) ?
C2' C3' . 1.372(4) ?
C2' H2'A . 0.9300 ?
C3' C4' . 1.380(4) ?
C3' H3'A . 0.9300 ?
C4' C5' . 1.376(4) ?
C5' C6' . 1.377(4) ?
C5' H5'A . 0.9300 ?
C6' H6'A . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5 H5A O1 1_455 0.93 2.608 3.375(4) 140 y
C13 H13B O1 1_455 0.97 2.687 3.475(3) 139 y
C5' H5'A O3 1_455 0.93 2.419 3.198(3) 142 y
C8 H8A O3 3_655 0.97 2.556 3.424(3) 149 y
C4 H4A Cl1 3_545 0.93 2.941 3.764(3) 148 y
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
O2 S1 N12 C11 . . . . -172.55(18) ?
O3 S1 N12 C11 . . . . -43.0(2) ?
C1' S1 N12 C11 . . . . 72.1(2) y
O2 S1 N12 C13 . . . . 45.5(2) ?
O3 S1 N12 C13 . . . . 175.12(17) ?
C1' S1 N12 C13 . . . . -69.78(19) ?
C6 N1 C2 O1 . . . . -177.7(2) ?
C10 N1 C2 O1 . . . . 3.6(3) ?
C6 N1 C2 C3 . . . . 3.0(3) ?
C10 N1 C2 C3 . . . . -175.7(2) ?
O1 C2 C3 C4 . . . . 177.7(3) ?
N1 C2 C3 C4 . . . . -3.0(4) ?
C2 C3 C4 C5 . . . . 0.9(5) ?
C3 C4 C5 C6 . . . . 1.5(5) ?
C4 C5 C6 N1 . . . . -1.5(4) ?
C4 C5 C6 C7 . . . . 178.7(3) ?
C2 N1 C6 C5 . . . . -0.8(3) ?
C10 N1 C6 C5 . . . . 177.8(2) ?
C2 N1 C6 C7 . . . . 179.0(2) ?
C10 N1 C6 C7 . . . . -2.4(3) ?
C5 C6 C7 C8 . . . . -147.4(2) ?
N1 C6 C7 C8 . . . . 32.8(3) ?
C5 C6 C7 C13 . . . . 90.2(3) ?
N1 C6 C7 C13 . . . . -89.6(3) ?
C6 C7 C8 C9 . . . . -62.1(3) ?
C13 C7 C8 C9 . . . . 60.5(3) ?
C7 C8 C9 C10 . . . . 62.6(3) ?
C7 C8 C9 C11 . . . . -61.9(3) ?
C6 N1 C10 C9 . . . . 2.5(3) ?
C2 N1 C10 C9 . . . . -178.8(2) ?
C8 C9 C10 N1 . . . . -33.3(3) ?
C11 C9 C10 N1 . . . . 89.4(3) ?
C13 N12 C11 C9 . . . . -60.2(3) ?
S1 N12 C11 C9 . . . . 156.07(18) ?
C10 C9 C11 N12 . . . . -62.0(3) ?
C8 C9 C11 N12 . . . . 61.6(3) ?
C11 N12 C13 C7 . . . . 58.3(3) ?
S1 N12 C13 C7 . . . . -157.68(17) ?
C6 C7 C13 N12 . . . . 64.2(3) ?
C8 C7 C13 N12 . . . . -58.2(3) ?
O2 S1 C1' C6' . . . . -15.8(3) ?
O3 S1 C1' C6' . . . . -146.5(2) ?
N12 S1 C1' C6' . . . . 99.0(2) ?
O2 S1 C1' C2' . . . . 165.7(2) ?
O3 S1 C1' C2' . . . . 35.0(2) ?
N12 S1 C1' C2' . . . . -79.4(2) y
C6' C1' C2' C3' . . . . -1.3(4) ?
S1 C1' C2' C3' . . . . 177.2(2) ?
C1' C2' C3' C4' . . . . 1.0(4) ?
C2' C3' C4' C5' . . . . 0.4(5) ?
C2' C3' C4' Cl1 . . . . -179.7(2) ?
C3' C4' C5' C6' . . . . -1.5(4) ?
Cl1 C4' C5' C6' . . . . 178.7(2) ?
C4' C5' C6' C1' . . . . 1.2(4) ?
C2' C1' C6' C5' . . . . 0.2(4) ?
S1 C1' C6' C5' . . . . -178.2(2) ?
