Supramolecular Packing of a Series of <i>N</i>-Phenylamides and the Role of NH···O=C Interactions.
Pagliari, Anderson B.; Orlando, Tainára; Salbego, Paulo R. S.; Zimmer, Geórgia C; Hörner, Manfredo; Zanatta, Nilo; Bonacorso, Helio G.; Martins, Marcos A. P.; ACS omega 3 (2018) 13850–13861; doi:10.1021/acsomega.8b01801

data_4515880
_publ_section_title
;
 Supramolecular Packing of a Series of <i>N</i>-Phenylamides and the Role
 of NH&#x00B7;&#x00B7;&#x00B7;O=C Interactions.
;
_journal_issue                   10
_journal_name_full               'ACS omega'
_journal_page_first              13850
_journal_page_last               13861
_journal_paper_doi               10.1021/acsomega.8b01801
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          'C8 H6 Br3 N O'
_chemical_formula_moiety         'C8 H6 Br3 N O'
_chemical_formula_sum            'C8 H6 Br3 N O'
_chemical_formula_weight         371.87
_chemical_name_systematic
;
2,2,2-Tribromo-<i>N</i>-phenylacetamide
;
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cct2mn4
_audit_creation_method           SHELXL-97
_audit_update_record
;
2009-09-10 deposited with the CCDC.
2015-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1863(8)
_cell_length_b                   9.1483(7)
_cell_length_c                   11.8856(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      20.65
_cell_measurement_theta_min      4.84
_cell_volume                     1107.59(15)
_computing_cell_refinement       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_collection       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_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      299(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2653
_diffrn_reflns_theta_full        66.95
_diffrn_reflns_theta_max         66.95
_diffrn_reflns_theta_min         4.83
_diffrn_standards_decay_%        1.5
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    13.218
_exptl_absorpt_correction_T_max  0.1782
_exptl_absorpt_correction_T_min  0.0371
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North <i>et al.</i>, 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.857
_refine_diff_density_min         -1.176
_refine_ls_abs_structure_details 'Flack (1983), 276 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(13)
_refine_ls_extinction_coef       0.0035(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1311
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0792
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1659P)^2^+2.9656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2325
_refine_ls_wR_factor_ref         0.2372
_reflns_number_gt                1237
_reflns_number_total             1311
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ao8b01801_si_007.cif
_cod_data_source_block           I
_cod_database_code               4515880