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_7229613
_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_absolute_configuration unk
_chemical_formula_moiety         'C12  H10  N3  O1  I1'
_chemical_formula_sum            'C12 H10 I N3 O'
_chemical_formula_weight         339.13
_chemical_name_systematic        '1-(4-iodophenyl)-3-phenyltriazenide N1-oxide'
_chemical_properties_physical    Air-stable.
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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             2017-04-25T10:02:24-00:00
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7465(3)
_cell_length_b                   9.9491(6)
_cell_length_c                   26.6177(14)
_cell_measurement_reflns_used    2524
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.746
_cell_measurement_theta_min      2.185
_cell_measurement_wavelength     0.71073
_cell_volume                     1256.98(13)
_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 0.989
_diffrn_measured_fraction_theta_max 0.98
_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  0.047
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.98
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            14579
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.278
_diffrn_reflns_theta_min         1.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.535
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5302
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_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          0.328
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.373
_refine_diff_density_min         -1.031
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.048(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0629P)^2^+0.5420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                1758
_reflns_number_total             2719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce02015e2.cif
_cod_data_source_block           shelx_CCDC4
_cod_depositor_comments
'Adding full bibliography for 7229609--7229613.cif.'
_cod_database_code               7229613