C—H···O and C—H···N interactions in three hexahydrocycloocta[<i>b</i>]pyridine-3-carbonitriles
Vishnupriya, R.; Suresh, J.; Maharani, S.; Kumar, R. Ranjith; Acta Crystallographica Section C 70 (2014) 236–240; doi:10.1107/S2053229614000291

data_2019433
_publ_section_title
;
 C---H&#x00B7;&#x00B7;&#x00B7;O and C---H&#x00B7;&#x00B7;&#x00B7;N
 interactions in three
 hexahydrocycloocta[<i>b</i>]pyridine-3-carbonitriles
;
_journal_coeditor_code           OV3043
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              236
_journal_page_last               240
_journal_paper_doi               10.1107/S2053229614000291
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C20 H21 N3 O3'
_chemical_formula_moiety         'C20 H21 N3 O3'
_chemical_formula_sum            'C20 H21 N3 O3'
_chemical_formula_weight         351.40
_chemical_name_systematic
2-Ethoxy-4-(3-nitrophenyl)-5,6,7,8,9,10-hexahydrocycloocta[<i>b</i>]pyridine-3-carbonitrile
_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
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.566(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2948(6)
_cell_length_b                   11.0251(4)
_cell_length_c                   14.0788(5)
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2
_cell_volume                     1829.36(13)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII 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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16156
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.46
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.234
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0645P)^2^+0.3091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                2571
_reflns_number_total             3399
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ov3043sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        1829.36(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2019433
_cod_database_fobs_code          2019433