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_2016286
_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          'C12 H12 Br N O'
_chemical_formula_moiety         'C12 H12 Br N O'
_chemical_formula_sum            'C12 H12 Br N O'
_chemical_formula_weight         266.14
_chemical_name_systematic
;
(2Z)-1-(4-Bromophenyl)-2-(pyrrolidin-2-ylidene)ethanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.1360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6636(3)
_cell_length_b                   18.9255(9)
_cell_length_c                   10.0500(5)
_cell_measurement_reflns_used    4950
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.30
_cell_volume                     1074.42(9)
_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  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9815
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    3.797
_exptl_absorpt_correction_T_max  0.5173
_exptl_absorpt_correction_T_min  0.3340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS in SAINT-NT; Bruker, 2005)
Ratio of minimum to maximum apparent transmission:  0.688943.
In the Tmin line above, Tmin=Tmax*min_to_max_ratio
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.599
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0239
_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^)+(0.0387P)^2^+0.4602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0682
_reflns_number_gt                2307
_reflns_number_total             2595
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            av3112.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2016286
_cod_database_fobs_code          2016286