Evaluation of viability of halogen⋯O2N interactions: Insight from crystal packing in a series of isomeric halo and nitro substituted triaryl compounds with modular positioning of halogen and NO2 groups
Ramana, C. V.; Goriya, Yogesh; Durugkar, Kulbhushan A.; Chatterjee, Soumitra; Krishnaswamy, Shobhana; Gonnade, Rajesh G.; CrystEngComm 15 (2013) 5283–; doi:10.1039/c3ce40192h

data_7209869
_publ_section_title
;
 Evaluation of viability of halogen&#x22EF;O2N interactions: Insight from
 crystal packing in a series of isomeric halo and nitro substituted
 triaryl compounds with modular positioning of halogen and NO2 groups
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              5283
_journal_paper_doi               10.1039/c3ce40192h
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C14 H9 Cl N4 O2'
_chemical_formula_sum            'C14 H9 Cl N4 O2'
_chemical_formula_weight         300.70
_chemical_melting_point          223.5(5)
_chemical_name_systematic
;
? 4-(3-Chlorophenyl)-1-(4-nitrophenyl)-1H-1,2,3-triazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.543(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.550(5)
_cell_length_b                   5.256(3)
_cell_length_c                   29.749(18)
_cell_measurement_reflns_used    1212
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      22.59
_cell_measurement_theta_min      2.42
_cell_volume                     1328.2(14)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_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  0.0618
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            6072
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'bruker sadabs'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+0.5779P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1594
_reflns_number_gt                1548
_reflns_number_total             2330
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce40192h.txt
_cod_data_source_block           3N4Cl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '223-224' was changed to '223.5(5)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1328.1(14)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7209869