Intramolecular six-membered N–H⋯Br and N–H⋯I hydrogen bonding in aromatic amides in the absence of competing interactions
Zhu, Yuan-Yuan; Jiang, Long; Li, Zhan-Ting; CrystEngComm 11 (2009) 235–; doi:10.1039/b814859g

data_7200410
_publ_section_title
;
 Intramolecular six-membered N--H&#x22EF;Br and N--H&#x22EF;I hydrogen
 bonding in aromatic amides in the absence of competing interactions
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              235
_journal_paper_doi               10.1039/b814859g
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C37 H35 Br N2 O2, C4 H8 O2'
_chemical_formula_sum            'C41 H43 Br N2 O4'
_chemical_formula_weight         707.68
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.568(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8909(11)
_cell_length_b                   10.2401(9)
_cell_length_c                   28.515(3)
_cell_measurement_reflns_used    3686
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.454
_cell_measurement_theta_min      4.562
_cell_volume                     3468.6(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0932
_diffrn_reflns_av_sigmaI/netI    0.1025
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            19939
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    1.230
_exptl_absorpt_correction_T_max  0.6589
_exptl_absorpt_correction_T_min  0.6261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         7539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.896
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0651P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1418
_reflns_number_gt                4374
_reflns_number_total             7539
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b814859g.txt
_cod_data_source_block           cd27640
_cod_original_cell_volume        3468.6(5)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7200410