Revisiting 2-chloro-4-nitroaniline: analysis of intricate supramolecular ordering of a triclinic polymorph featuring high Z value and strong second harmonic generation
Medviediev, Volodymyr; Shishkina, Svitlana V.; Ribalka, Andrii; Zaręba, Jan Kazimierz; Drozd, Marek; Daszkiewicz, Marek; CrystEngComm  (2020) –; doi:10.1039/D0CE00582G

data_7240813
_publ_section_title
;
 Revisiting 2-chloro-4-nitroaniline: analysis of intricate supramolecular
 ordering of a triclinic polymorph featuring high Z value and strong
 second harmonic generation
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00582G
_journal_year                    2020
_chemical_formula_moiety         'C6 H5 Cl N2 O2'
_chemical_formula_sum            'C6 H5 Cl N2 O2'
_chemical_formula_weight         172.57
_chemical_name_systematic        2-Chloro-4-nitroaniline
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-16 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                89.503(4)
_cell_angle_beta                 88.612(4)
_cell_angle_gamma                86.402(4)
_cell_formula_units_Z            8
_cell_length_a                   3.77550(19)
_cell_length_b                   13.5798(7)
_cell_length_c                   28.5543(14)
_cell_measurement_reflns_used    4893
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      26.0560
_cell_measurement_theta_min      3.0290
_cell_volume                     1460.64(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.4350
_diffrn_detector_type            'Sapphire1, long nozzle'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -43.00   80.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       31.0000  -84.0000  -20.0000 246

  2 omega  -10.00   70.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       31.0000   45.0000  170.0000 160

  3 omega  -65.00   90.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       31.0000   20.0000  -20.0000 310

  4 omega  -15.00   60.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       31.0000  -84.0000  170.0000 150

  5 omega  -30.00   40.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       31.0000  -84.0000  260.0000 140

  6 omega  -15.00   90.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000   55.0000   45.0000 210

  7 omega    0.00   67.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7560  -38.0000  150.0000 134

  8 omega  -41.00   -1.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7561   38.0000   60.0000 80

  9 omega    0.00   71.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7560   77.0000  120.0000 142

 10 omega  -19.00   49.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7560   77.0000    0.0000 136

 11 omega   49.00   90.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7560  179.0000   90.0000 82

 12 omega  -65.00  -56.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0690  179.0000   30.0000 18

 13 omega  -63.00   -6.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0686   38.0000  120.0000 114

 14 omega  -30.00   66.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0686   38.0000  -30.0000 192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0339645000
_diffrn_orient_matrix_UB_12      -0.0506034000
_diffrn_orient_matrix_UB_13      -0.0017425000
_diffrn_orient_matrix_UB_21      0.0084041000
_diffrn_orient_matrix_UB_22      0.0038274000
_diffrn_orient_matrix_UB_23      -0.0247863000
_diffrn_orient_matrix_UB_31      0.1850138000
_diffrn_orient_matrix_UB_32      -0.0127958000
_diffrn_orient_matrix_UB_33      0.0002058000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0805
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            17888
_diffrn_reflns_point_group_measured_fraction_full 0.906
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.607
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_preparation       SHG
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 2021 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     793
_refine_ls_number_reflns         9363
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0773
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0832P)^2^+0.9976P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1877
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.819
_reflns_Friedel_fraction_max     0.819
_reflns_number_gt                6211
_reflns_number_total             9363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00582g2.cif
_cod_data_source_block           v263_6b
_cod_original_cell_volume        1460.65(13)
_cod_database_code               7240813
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.735
_reflns_odcompleteness_completeness 91.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.21
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C5A(H5A), C6A(H6A), C3B(H3B), C5B(H5B), C6B(H6B), C3C(H3C),
 C5C(H5C), C6C(H6C), C3D(H3D), C5D(H5D), C6D(H6D), C3E(H3E), C5E(H5E), C6E(H6E),
  C3F(H3F), C5F(H5F), C6F(H6F), C3G(H3G), C5G(H5G), C6G(H6G), C3H(H3H),
 C5H(H5H), C6H(H6H)
2.b X=CH2 refined with riding coordinates:
 N1A(H1AB,H1AA), N1B(H1BA,H1BB), N1C(H1CB,H1CA), N1D(H1DA,H1DB), N1E(H1EB,
 H1EA), N1F(H1FA,H1FB), N1G(H1GB,H1GA), N1H(H1HA,H1HB)
;
_shelx_res_checksum              71757
_olex2_date_sample_data_collection 2016-11-23
_olex2_submission_special_instructions 'No special instructions were received'