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_2244234
_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          'C17 H17 N3 O5 S'
_chemical_formula_moiety         'C17 H17 N3 O5 S'
_chemical_formula_sum            'C17 H17 N3 O5 S'
_chemical_formula_weight         375.39
_chemical_name_common
;
(7<i>R</i>,9<i>R</i>)-<i>N</i>-[(3-nitrophenyl)sulfonyl]cytisine
;
_chemical_name_systematic
(1<i>R</i>,5<i>R</i>)-3-((3-nitrophenyl)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      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 94.03(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.040(2)
_cell_length_b                   6.2621(13)
_cell_length_c                   12.424(3)
_cell_measurement_reflns_used    5501
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      71.3670
_cell_measurement_theta_min      4.0060
_cell_volume                     856.8(3)
_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      296(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 0.990
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7776
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.460
_diffrn_reflns_theta_min         3.566
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63895
_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    1.455
_exptl_crystal_description       prizmatic
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.224
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 579 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.017(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2446
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0754P)^2^+0.1248P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                2363
_reflns_number_total             2446
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5674sup1.cif
_cod_data_source_block           III
_cod_depositor_comments
'Adding full bibliography for 2244232--2244234.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2244234
_cod_database_fobs_code          2244234
_shelx_hkl_checksum              39136
_shelx_res_checksum              24817