Hydrogen-bonding patterns in enaminones: (2<i>Z</i>)-1-(4-bromophenyl)-2-(pyrrolidin-2-ylidene)ethanone and its piperidin-2-ylidene and azepan-2-ylidene analogues
Balderson, James L.; Fernandes, Manuel A.; Michael, Joseph P.; Perry, Christopher B.; Acta Crystallographica Section C 63 (2007) o734–o738; doi:10.1107/S0108270107053206

data_2016288
_publ_section_title
;
 Hydrogen-bonding patterns in enaminones:
 (2<i>Z</i>)-1-(4-bromophenyl)-2-(pyrrolidin-2-ylidene)ethanone and its
 piperidin-2-ylidene and azepan-2-ylidene analogues
;
_journal_coeditor_code           AV3112
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o734
_journal_page_last               o738
_journal_paper_doi               10.1107/S0108270107053206
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H16 Br N O'
_chemical_formula_moiety         'C14 H16 Br N O'
_chemical_formula_sum            'C14 H16 Br N O'
_chemical_formula_weight         294.19
_chemical_name_systematic
;
(2Z)-2-(Azepan-2-ylidene)-1-(4-bromophenyl)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
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.702(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2867(3)
_cell_length_b                   8.2416(2)
_cell_length_c                   12.9404(4)
_cell_measurement_reflns_used    4189
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.95
_cell_volume                     1287.58(6)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-NT (Bruker, 2005)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg,
1999)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9654
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    3.176
_exptl_absorpt_correction_T_max  0.6473
_exptl_absorpt_correction_T_min  0.3052
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '[face-indexed using XPREP (Bruker, 2005)]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.409
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0326P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0648
_reflns_number_gt                2401
_reflns_number_total             3103
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            av3112.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2016288
_cod_database_fobs_code          2016288