Structural diversity of hydrogen-bonded complexes comprising phenol-based and pyridine-based components: NLO properties, crystallographic and spectroscopic studies
Bryndal, Iwona; Drozd, Marek; Lis, Tadeusz; Zaręba, Jan Kazimierz; Ratajczak, Henryk; CrystEngComm  (2020) –; doi:10.1039/D0CE00606H

data_7240633
_publ_section_title
;
 Structural diversity of hydrogen-bonded complexes comprising phenol-based
 and pyridine-based components: NLO properties, crystallographic and
 spectroscopic studies
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00606H
_journal_year                    2020
_chemical_formula_moiety         'C6 H Cl4 O, C8 H12 N'
_chemical_formula_sum            'C14 H13 Cl4 N O'
_chemical_formula_weight         353.05
_chemical_name_common
'2,3,6-trimethylpyridinium 2,3,5,6-tetrachlorophenolate'
_chemical_name_systematic
'2,3,6-trimethylpyridinium 2,3,5,6-tetrachlorophenolate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2020-03-19 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.6730(18)
_cell_length_b                   15.707(3)
_cell_length_c                   24.892(5)
_cell_measurement_reflns_used    5780
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.528
_cell_measurement_theta_min      2.949
_cell_volume                     3000.0(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3456
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11914
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         30.597
_diffrn_reflns_theta_min         2.955
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.51(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         7676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0263P)^2^+0.8733P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0836
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                6908
_reflns_number_total             7676
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00606h2.cif
_cod_data_source_block           3k4chfba
_cod_database_code               7240633
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.705
_shelx_estimated_absorpt_t_max   0.788
_shelx_res_checksum              41668