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_7229610
_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 H11 N3 O'
_chemical_formula_sum            'C12 H11 N3 O'
_chemical_formula_weight         213.24
_chemical_melting_point          121
_chemical_name_systematic        '1,3-bis(phenyl)triazene N3-hyroxide'
_chemical_properties_physical    Air-stable
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-08-31 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.382(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4917(5)
_cell_length_b                   16.1489(13)
_cell_length_c                   12.4976(10)
_cell_measurement_reflns_used    979
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      19.41
_cell_measurement_theta_min      3.02
_cell_volume                     1090.20(16)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0837
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11977
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.176
_diffrn_reflns_theta_min         3.018
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.2174
_refine_ls_R_factor_gt           0.0687
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0763P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.2041
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1177
_reflns_number_total             3451
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce02015e2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7229609--7229613.cif.'
_cod_database_code               7229610
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              35257