Understanding the crystalline formation of triazene N-oxides and the role of halogen⋯π interactions
Martins, Marcos A. P.; Salbego, Paulo R. S.; de Moraes, Guilherme A.; Bender, Caroline R.; Zambiazi, Priscilla J.; Orlando, Tainára; Pagliari, Anderson B.; Frizzo, Clarissa P.; Hörner, Manfredo; CrystEngComm 20 (2018) 96–; doi:10.1039/C7CE02015E

data_7229612
_publ_section_title
;
 Understanding the crystalline formation of triazene N-oxides and the role
 of halogen&#x22EF;\p interactions
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              96
_journal_paper_doi               10.1039/C7CE02015E
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C12 H10 Br N3 O'
_chemical_formula_sum            'C12 H10 Br N3 O'
_chemical_formula_weight         292.14
_chemical_name_systematic        '1-(4-bromophenyl)-3-phenyltriazenide N1-oxide'
_chemical_properties_physical    Air-stable.
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2017-05-15T13:38:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2017-08-25 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.462(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2398(3)
_cell_length_b                   9.7185(5)
_cell_length_c                   19.5527(10)
_cell_measurement_reflns_used    3787
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.182
_cell_measurement_theta_min      2.343
_cell_measurement_wavelength     0.71073
_cell_volume                     1178.17(10)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       scans
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11495
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.162
_diffrn_reflns_theta_min         2.096
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.475
_exptl_absorpt_correction_T_max  0.543
_exptl_absorpt_correction_T_min  0.440
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method
'Recrystallized from a fraction of ethanol/pyridine solvents, which after, approximately, five days of slow evaporation resulted in yellow crystals with needle shape.'
_exptl_crystal_size_max          0.868
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0283P)^2^+0.2015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0727
_reflns_Friedel_coverage         0
_reflns_number_gt                1813
_reflns_number_total             2602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce02015e2.cif
_cod_data_source_block           shelx_CCDC3
_cod_depositor_comments
'Adding full bibliography for 7229609--7229613.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7229612