Syntheses, crystal structures and Hirshfeld surface analyses of <i>N</i>-aryl-sulfonyl derivatives of cytisine.
Okmanov, Rasul Ya; Olimova, Manzura I.; Karabaeva, Surayyo B.; Sapaev, Frunza A.; Abdireymov, Kudaybergen B.; Acta crystallographica. Section E, Crystallographic communications 79 (2023) 313–318; doi:10.1107/S2056989023001950

data_2244232
_publ_section_title
;
 Syntheses, crystal structures and Hirshfeld surface analyses of
 <i>N</i>-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          'C19 H22 N2 O3 S'
_chemical_formula_moiety         'C19 H22 N2 O3 S'
_chemical_formula_sum            'C19 H22 N2 O3 S'
_chemical_formula_weight         358.44
_chemical_name_common
;
(7<i>R</i>,9<i>R</i>)-<i>N</i>-[(4-Ethylphenyl)sulfonyl]cytisine
;
_chemical_name_systematic
(1<i>R</i>,5<i>R</i>)-3-[(4-Ethylphenyl)sulfonyl]-1,2,3,4,5,6-hexahydro-8<i>H</i>-1,5-methanopyrido[1,2-<i>a</i>][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                   6.9503(14)
_cell_length_b                   10.585(2)
_cell_length_c                   24.975(5)
_cell_measurement_reflns_used    10591
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      70.8650
_cell_measurement_theta_min      3.5140
_cell_volume                     1837.4(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
;
<i>SHELXL2018/3</i> (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 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17786
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.420
_diffrn_reflns_theta_min         3.539
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       prizmatic
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.444
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1319 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.012(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0376
_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/[\s^2^(Fo^2^)+(0.0523P)^2^+0.0534P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0937
_reflns_number_gt                3348
_reflns_number_total             3553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5674sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 2244232--2244234.cif.'
_cod_original_cell_volume        1837.5(6)
_cod_database_code               2244232
_cod_database_fobs_code          2244232
_shelx_hkl_checksum              51140
_shelx_res_checksum              85393