Synthesis, crystal structure and Hirshfeld analysis of a crystalline compound comprising a 1/1 mixture of 1-[(1<i>R</i>,4<i>S</i>)- and 1-[(1<i>S</i>,4<i>R</i>)-1,7,7-trimethyl-2-oxobicyclo[2.2.1]heptan-3-ylidene]hydrazinecarbothioamide
Pires, Fabrício Carvalho; Bresolin, Leandro; Gervini, Vanessa Carratu; Tirloni, Bárbara; Bof de Oliveira, Adriano; Acta Crystallographica Section E 76 (2020) 115–120; doi:10.1107/S2056989019016980

data_2243229
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld analysis of a crystalline
 compound comprising a 1/1 mixture of 1-[(1<i>R</i>,4<i>S</i>)- and
 1-[(1<i>S</i>,4<i>R</i>)-1,7,7-trimethyl-2-oxobicyclo[2.2.1]heptan-3-ylidene]hydrazinecarbothioamide
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              115
_journal_page_last               120
_journal_paper_doi               10.1107/S2056989019016980
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C11 H17 N3 O S'
_chemical_formula_moiety         'C11 H17 N3 O S'
_chemical_formula_sum            'C11 H17 N3 O S'
_chemical_formula_weight         239.34
_chemical_name_systematic
;
1-[(1<i>R</i>,4<i>S</i>)-1,7,7-Trimethyl-2-oxobicyclo[2.2.1]heptan-3-\
ylidene]hydrazinecarbothioamide--\
1-[(1<i>S</i>,4<i>R</i>)-1,7,7-trimethyl-2-oxobicyclo[2.2.1]heptan-3-\
ylidene]hydrazinecarbothioamide (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 121.9320(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   26.6370(9)
_cell_length_b                   10.7617(4)
_cell_length_c                   20.2108(7)
_cell_measurement_reflns_used    9117
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      71.94
_cell_measurement_theta_min      2.58
_cell_volume                     4916.9(3)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010) and enCIFer (Allen <i>et al.</i>,  2004)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT2014/5</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type
'Bruker D8 Quest Photon II area detector diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            47973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.310
_diffrn_reflns_theta_min         3.911
_diffrn_source                   'microfocus X ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.211
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.699
_exptl_crystal_size_mid          0.455
_exptl_crystal_size_min          0.436
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.332
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0548P)^2^+5.1392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                4783
_reflns_number_total             4791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            rz5268sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2243229
_cod_database_fobs_code          2243229
_shelx_estimated_absorpt_t_min   0.307
_shelx_estimated_absorpt_t_max   0.446
_shelx_hkl_checksum              58013
_shelx_res_checksum              50850