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_7240632
_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 H2 Cl4 O, C7 H9 N'
_chemical_formula_sum            'C13 H11 Cl4 N O'
_chemical_formula_weight         339.03
_chemical_name_common
'3,5-dimethylpyridine 2,3,5,6-tetrachlorophenol'
_chemical_name_systematic
'3,5-dimethylpyridine 2,3,5,6-tetrachlorophenol'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_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                 100.02(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.428(3)
_cell_length_b                   6.0198(12)
_cell_length_c                   14.604(3)
_cell_measurement_reflns_used    5060
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.560
_cell_measurement_theta_min      2.827
_cell_volume                     1422.2(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0105
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5393
_diffrn_reflns_point_group_measured_fraction_full 0.674
_diffrn_reflns_point_group_measured_fraction_max 0.582
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         30.628
_diffrn_reflns_theta_min         2.833
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  0.813
_exptl_absorpt_correction_T_min  0.742
_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    1.583
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2572
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0174
_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^)+(0.0307P)^2^+0.3648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0483
_refine_ls_wR_factor_ref         0.0483
_reflns_Friedel_coverage         0.275
_reflns_Friedel_fraction_full    0.348
_reflns_Friedel_fraction_max     0.251
_reflns_number_gt                2569
_reflns_number_total             2572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00606h2.cif
_cod_data_source_block           35l4chfa
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7240632
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.704
_shelx_estimated_absorpt_t_max   0.791
_shelx_res_checksum              94591