Nonlinear optical organic–inorganic crystals: synthesis, structural analysis and verification of harmonic generation in tri-(<i>o</i>-chloroanilinium nitrate)
Athmani, Hamza; Kijatkin, Christian; Benali-Cherif, Rim; Pillet, Sébastien; Schaniel, Dominik; Imlau, Mirco; Benali-Cherif, Nourredine; Bendeif, El-Eulmi; Acta Crystallographica Section A 75 (2019) 107–114; doi:10.1107/S2053273318014122

data_2311098
_publ_section_title
;
 Nonlinear optical organic--inorganic crystals: synthesis, structural
 analysis and verification of harmonic generation in
 tri-(<i>o</i>-chloroanilinium nitrate)
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section A'
_journal_page_first              107
_journal_page_last               114
_journal_paper_doi               10.1107/S2053273318014122
_journal_volume                  75
_journal_year                    2019
_chemical_formula_moiety         'C6 H7 Cl N +, N O3 -'
_chemical_formula_sum            'C6 H7 Cl N2 O3'
_chemical_formula_weight         190.59
_chemical_name_common            'tri-(o-Chloroanilinium Nitrate'
_chemical_name_systematic        'tri-(o-Chloroanilinium Nitrate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   16.8015(5)
_cell_length_b                   6.5945(2)
_cell_length_c                   22.4243(6)
_cell_measurement_reflns_used    117559
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.889
_cell_measurement_theta_min      3.030
_cell_volume                     2484.56(12)
_computing_cell_refinement
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2017)
;
_computing_data_collection
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2017)
;
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and and ORTEP-3 for Windows (Farrugia,
1997)
;
_computing_publication_material
;
'enCIFer (Allen <i>et al.</i>, 2004)'
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4508
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            117559
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.889
_diffrn_reflns_theta_min         3.030
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.429
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       prism
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 3499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.050(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         13028
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0342P)^2^+0.1157P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                9377
_reflns_number_total             13028
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lk5035sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
;
          Adding full bibliography for 2311098.cif.

2019-09-03
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '3((C6 H7 Cl N)+, (NO3)-)'
_cod_original_formula_sum        'C18 H21 Cl3 N6 O9'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     571.76
_cod_database_code               2311098
_cod_database_fobs_code          2311098
_shelx_estimated_absorpt_t_min   0.728
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              12694
_shelx_hkl_checksum              88276