Forced twin-chair conformation in 7-benzoyl- and 7-phenylacetyl-<i>r</i>-2,<i>c</i>-4,<i>t</i>-6,<i>t</i>-8-tetraphenyl-3-thia-7-azabicyclo[3.3.1]nonanes with 1,3-diaxial phenyl groups in the piperidine ring: single- and double-layered supramolecular sheets built from C—H···O and C—H···π(arene) hydrogen bonds
Sakthivel, Chinniah; Jeyaraman, Ramasubbu; Acta Crystallographica Section C 66 (2010) o396–o400; doi:10.1107/S0108270110023115

data_2017750
_publ_section_title
;
 Forced twin-chair conformation in 7-benzoyl- and
 7-phenylacetyl-<i>r</i>-2,<i>c</i>-4,<i>t</i>-6,<i>t</i>-8-tetraphenyl-3-thia-7-azabicyclo[3.3.1]nonanes
 with 1,3-diaxial phenyl groups in the piperidine ring: single- and
 double-layered supramolecular sheets built from
 C---H&#x00B7;&#x00B7;&#x00B7;O and
 C---H&#x00B7;&#x00B7;&#x00B7;\p(arene) hydrogen bonds
;
_journal_coeditor_code           GD3335
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o396
_journal_page_last               o400
_journal_paper_doi               10.1107/S0108270110023115
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C39 H35 N O S'
_chemical_formula_moiety         'C39 H35 N O S'
_chemical_formula_sum            'C39 H35 N O S'
_chemical_formula_weight         565.75
_chemical_name_common
;
N-Phenylacetyl-<i>r</i>-2,<i>c</i>-4,<i>t</i>-6,<i>t</i>-8\
-tetraphenyl-3-thia-7-azabicyclo[3.3.1]nonane
;
_chemical_name_systematic
;
2-phenyl-1-(<i>r</i>-2,<i>c</i>-4,<i>t</i>-6,<i>t</i>-8-\
tetraphenyl-3-thia-7-azabicyclo[3.3.1]nonan-7-yl)ethanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 93.2450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8724(7)
_cell_length_b                   9.4863(3)
_cell_length_c                   19.2376(8)
_cell_measurement_reflns_used    8894
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2075
_cell_measurement_theta_min      2.379
_cell_volume                     3074.2(2)
_computing_cell_refinement
;
APEX2 (Bruker, 2004) and SAINT (Bruker, 2004)
;
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction
;
SAINT (Bruker, 2004) and XPREP (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP32 (Farrugia, 1997) and PLATON (Spek, 2009)
;
_computing_publication_material
;
PLATON (Spek, 2009) and  publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29474
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '[SADABS (Bruker, 2004; Blessing, 1995)]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.202
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0542P)^2^+1.2416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1312
_reflns_number_gt                4500
_reflns_number_total             6045
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3335.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017750
_cod_database_fobs_code          2017750