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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/25/7212508.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7212508
loop_
_publ_author_name
'Podsiadło, Marcin'
'Jakóbek, Katarzyna'
'Katrusiak, Andrzej'
_publ_section_title
;
 Density, freezing and molecular aggregation in pyridazine, pyridine and
 benzene
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              2561
_journal_paper_doi               10.1039/c001153c
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         '3(C5 H5 N), C H4 O'
_chemical_formula_sum            'C16 H19 N3 O'
_chemical_formula_weight         269.34
_chemical_name_common            'pyridine:methanol 3:1 cocrystal'
_chemical_name_systematic
;
pyridine:methanol 3:1 cocrystal
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 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                 90.40(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.7710(14)
_cell_length_b                   5.5910(11)
_cell_length_c                   18.100(4)
_cell_measurement_reflns_used    4755
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.96
_cell_measurement_theta_min      3.01
_cell_volume                     685.2(2)
_computing_cell_refinement       'CrysAlisRED (Oxford Diffraction, 2004)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2004)'
_computing_data_reduction
'CrysAlisRED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A. 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'SHELXL--97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL--97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS--97 (Sheldrick, 1997)'
_diffrn_ambient_environment      'diamond-anvil cell'
_diffrn_ambient_pressure         1800000
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.395
_diffrn_measured_fraction_theta_max 0.395
_diffrn_measurement_device_type  'KM-4 CCD'
_diffrn_measurement_method       'φ- and ω-scans'
_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  0.2065
_diffrn_reflns_av_sigmaI/netI    0.1638
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4755
_diffrn_reflns_theta_full        24.96
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.28
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Correction for absorption of the diamond-anvil cell and the sample
were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam
Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr.
219, 461-467).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.301
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     27
_refine_ls_number_reflns         907
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      2.299
_refine_ls_R_factor_all          0.3587
_refine_ls_R_factor_gt           0.3001
_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/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2850
_refine_ls_wR_factor_ref         0.3070
_reflns_number_gt                585
_reflns_number_total             907
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c001153c.txt
_cod_data_source_block           pirmet_1.80GPa
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7212508
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N -0.3160(17) 1.011(3) 1.6577(19) 0.0485(16) Uiso 1 1 d G
C2 C -0.3802(16) 1.200(2) 1.6199(19) 0.0485(16) Uiso 1 1 d G
H2 H -0.4286 1.3319 1.6453 0.058 Uiso 1 1 calc R
C3 C -0.377(2) 1.205(2) 1.541(2) 0.0485(16) Uiso 1 1 d G
H3 H -0.4229 1.3410 1.5171 0.058 Uiso 1 1 calc R
C4 C -0.309(2) 1.022(3) 1.501(2) 0.0485(16) Uiso 1 1 d G
H4 H -0.3070 1.0264 1.4494 0.058 Uiso 1 1 calc R
C5 C -0.245(2) 0.833(2) 1.539(2) 0.0485(16) Uiso 1 1 d G
H5 H -0.1963 0.7011 1.5131 0.058 Uiso 1 1 calc R
C6 C -0.2483(18) 0.828(2) 1.617(2) 0.0485(16) Uiso 1 1 d G
H6 H -0.2019 0.6921 1.6414 0.058 Uiso 1 1 calc R
N11 N -0.8582(14) 0.418(3) 1.6460(14) 0.0485(16) Uiso 1 1 d G
C12 C -0.753(2) 0.697(2) 1.5564(15) 0.0485(16) Uiso 1 1 d G
H12 H -0.6977 0.8464 1.5472 0.058 Uiso 1 1 calc R
C13 C -0.7807(18) 0.627(2) 1.6305(14) 0.0485(16) Uiso 1 1 d G
H13 H -0.7437 0.7300 1.6686 0.058 Uiso 1 1 calc R
C14 C -0.803(2) 0.558(3) 1.4978(15) 0.0485(16) Uiso 1 1 d G
H14 H -0.7834 0.6079 1.4494 0.058 Uiso 1 1 calc R
C15 C -0.9082(14) 0.279(2) 1.5874(15) 0.0485(16) Uiso 1 1 d G
H15 H -0.9635 0.1300 1.5965 0.058 Uiso 1 1 calc R
C16 C -0.881(2) 0.349(2) 1.5133(15) 0.0485(16) Uiso 1 1 d G
H16 H -0.9176 0.2464 1.4752 0.058 Uiso 1 1 calc R
N21 N -0.215(2) 1.692(2) 1.367(2) 0.0485(16) Uiso 1 1 d G
C22 C -0.206(3) 1.3346(19) 1.308(3) 0.0485(16) Uiso 1 1 d G
H22 H -0.1340 1.2124 1.2856 0.058 Uiso 1 1 calc R
C23 C -0.398(3) 1.3222(15) 1.310(2) 0.0485(16) Uiso 1 1 d G
H23 H -0.4639 1.1912 1.2903 0.058 Uiso 1 1 calc R
C24 C -0.499(2) 1.4948(13) 1.342(3) 0.0485(16) Uiso 1 1 d G
H24 H -0.6362 1.4858 1.3436 0.058 Uiso 1 1 calc R
C25 C -0.407(2) 1.6797(17) 1.370(3) 0.0485(16) Uiso 1 1 d G
H25 H -0.4790 1.8019 1.3923 0.058 Uiso 1 1 calc R
C26 C -0.114(2) 1.519(2) 1.336(3) 0.0485(16) Uiso 1 1 d G
H26 H 0.0232 1.5284 1.3342 0.058 Uiso 1 1 calc R
O31 O -0.790(3) 1.009(2) 1.345(3) 0.049(4) Uiso 1 1 d G
H31 H -0.8530 0.9000 1.3635 0.058 Uiso 1 1 calc R
C32 C -0.796(4) 0.984(4) 1.260(4) 0.049(4) Uiso 1 1 d .
H321 H -0.8605 0.8365 1.2472 0.063 Uiso 1 1 calc R
H322 H -0.6637 0.9827 1.2415 0.063 Uiso 1 1 calc R
H323 H -0.8675 1.1156 1.2393 0.063 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C6 115.8
N1 C2 C3 121.6
C4 C3 C2 122.6
C5 C4 C3 115.8
C4 C5 C6 121.6
N1 C6 C5 122.6
C13 N11 C15 116.2
C14 C12 C13 123.4
N11 C13 C12 120.4
C16 C14 C12 116.2
N11 C15 C16 123.4
C14 C16 C15 120.4
C25 N21 C26 120.0
C23 C22 C26 119.8
C22 C23 C24 120.0
C25 C24 C23 120.2
N21 C25 C24 119.8
C22 C26 N21 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.330(8)
N1 C6 1.345(8)
C2 C3 1.422(8)
C3 C4 1.345(8)
C4 C5 1.330(8)
C5 C6 1.422(8)
N11 C13 1.312(8)
N11 C15 1.356(8)
C12 C14 1.356(8)
C12 C13 1.411(8)
C14 C16 1.312(8)
C15 C16 1.410(8)
N21 C25 1.308(5)
N21 C26 1.312(5)
C22 C23 1.308(5)
C22 C26 1.310(5)
C23 C24 1.312(5)
C24 C25 1.310(5)
O31 C32 1.53(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139197628
