#------------------------------------------------------------------------------
#$Date: 2025-08-19 20:17:10 +0200 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/2/24/11/2241108.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2241108
loop_
_publ_author_name
'Matsumoto, Kouzou'
'Kawashita, Kazuaki'
'Kannami, Masaki'
'Oda, Masaji'
_publ_section_title
;
 Crystal structure of tetrakis(1-oxidopyridin-2-yl)methane methanol
 tetrasolvate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o754
_journal_page_last               o755
_journal_paper_doi               10.1107/S2056989015016862
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C21 H16 N4 O4, 4C H4 O'
_chemical_formula_moiety         'C21 H16 N4 O4, 4(C H4 O)'
_chemical_formula_sum            'C25 H32 N4 O8'
_chemical_formula_weight         516.54
_chemical_name_common
'Tetrakis(pyridin-2-yl)methane tetraN-oxide methanol tetrasolvate'
_chemical_name_systematic
;
Tetrakis(1-oxidopyridin-2-yl)methane methanol tetrasolvate
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a'
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4474(4)
_cell_length_b                   14.4474(4)
_cell_length_c                   12.2965(5)
_cell_measurement_reflns_used    9662
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.6
_cell_volume                     2566.62(14)
_computing_cell_refinement
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_data_collection
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_data_reduction
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_molecular_graphics
;
Yadokari-XG 2009 (Wakita, 2001) and
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
Yadokari-XG 2009 (Wakita, 2001) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12321
_diffrn_reflns_theta_full        25.2
_diffrn_reflns_theta_max         27.4
_diffrn_reflns_theta_min         3.6
_exptl_absorpt_coefficient_mu    0.10
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         1470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.053
_refine_ls_R_factor_gt           0.049
_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/[σ²(Fo²)+(0.0821P)²+1.7364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.134
_refine_ls_wR_factor_ref         0.138
_reflns_number_gt                1289
_reflns_number_total             1470
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            is5417sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2566.62(18)
_cod_database_code               2241108
_cod_database_fobs_code          2241108
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z'
'-y+3/4, x+1/4, z+1/4'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-1/4'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'-y+1/4, x+1/4, -z+1/4'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.0000 0.2500 0.6250 0.0172(5) Uani d 1
C C2 -0.06345(8) 0.18960(8) 0.69738(9) 0.0181(3) Uani d 1
C C3 -0.15822(8) 0.17917(8) 0.68249(10) 0.0218(3) Uani d 1
H H1 -0.1873 0.2091 0.6228 0.026 Uiso calc 1
C C4 -0.21147(9) 0.12608(9) 0.75266(11) 0.0263(3) Uani d 1
H H2 -0.2762 0.1198 0.7416 0.032 Uiso calc 1
C C5 -0.16814(10) 0.08235(10) 0.83934(12) 0.0299(4) Uani d 1
H H3 -0.2030 0.0458 0.8887 0.036 Uiso calc 1
C C6 -0.07458(9) 0.09250(10) 0.85293(11) 0.0276(3) Uani d 1
H H4 -0.0449 0.0623 0.9120 0.033 Uiso calc 1
C C7 0.14412(17) 0.16009(17) 1.05514(18) 0.0626(6) Uani d 1
H H6 0.0822 0.1835 1.0727 0.094 Uiso calc 1
H H7 0.1792 0.2082 1.0169 0.094 Uiso calc 1
H H8 0.1764 0.1433 1.1224 0.094 Uiso calc 1
N N1 -0.02328(7) 0.14510(7) 0.78324(8) 0.0211(3) Uani d 1
O O1 0.06661(6) 0.15169(7) 0.79946(8) 0.0279(3) Uani d 1
O O2 0.13633(12) 0.08248(11) 0.98897(12) 0.0639(5) Uani d 1
H H5 0.1193 0.0987 0.9265 0.096 Uiso calc 1
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C2 . 2 109.77(9)
C2 C1 C2 . 16_556 109.32(4)
C2 C1 C2 2 16_556 109.32(4)
C2 C1 C2 . 15_556 109.32(4)
C2 C1 C2 2 15_556 109.32(4)
C2 C1 C2 16_556 15_556 109.77(9)
N1 C2 C3 . . 118.00(11)
N1 C2 C1 . . 117.29(9)
C3 C2 C1 . . 124.69(10)
C4 C3 C2 . . 121.63(11)
C4 C3 H1 . . 119.2
C2 C3 H1 . . 119.2
C3 C4 C5 . . 118.62(12)
C3 C4 H2 . . 120.7
C5 C4 H2 . . 120.7
C6 C5 C4 . . 119.34(12)
C6 C5 H3 . . 120.3
C4 C5 H3 . . 120.3
N1 C6 C5 . . 121.26(12)
N1 C6 H4 . . 119.4
C5 C6 H4 . . 119.4
O2 C7 H6 . . 109.5
O2 C7 H7 . . 109.5
H6 C7 H7 . . 109.5
O2 C7 H8 . . 109.5
H6 C7 H8 . . 109.5
H7 C7 H8 . . 109.5
O1 N1 C6 . . 118.73(10)
O1 N1 C2 . . 120.13(10)
C6 N1 C2 . . 121.13(11)
C7 O2 H5 . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.5472(11)
C1 C2 2 1.5472(11)
C1 C2 16_556 1.5472(11)
C1 C2 15_556 1.5472(11)
C2 N1 . 1.3656(16)
C2 C3 . 1.3895(16)
C3 C4 . 1.3874(18)
C3 H1 . 0.9500
C4 C5 . 1.3881(19)
C4 H2 . 0.9500
C5 C6 . 1.3698(19)
C5 H3 . 0.9500
C6 N1 . 1.3643(16)
C6 H4 . 0.9500
C7 O2 . 1.390(3)
C7 H6 . 0.9800
C7 H7 . 0.9800
C7 H8 . 0.9800
N1 O1 . 1.3174(14)
O2 H5 . 0.8400
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H5 O1 . 0.84 1.90 2.7285(15) 169
C4 H2 O1 14_456 0.95 2.37 3.290(2) 163
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion
C2 C1 C2 N1 2 -45.51(8)
C2 C1 C2 N1 16_556 74.40(6)
C2 C1 C2 N1 15_556 -165.42(10)
C2 C1 C2 C3 2 133.05(13)
C2 C1 C2 C3 16_556 -107.04(14)
C2 C1 C2 C3 15_556 13.14(11)
N1 C2 C3 C4 . 0.59(18)
C1 C2 C3 C4 . -177.96(10)
C2 C3 C4 C5 . -0.2(2)
C3 C4 C5 C6 . -0.2(2)
C4 C5 C6 N1 . 0.3(2)
C5 C6 N1 O1 . -179.29(12)
C5 C6 N1 C2 . 0.0(2)
C3 C2 N1 O1 . 178.83(10)
C1 C2 N1 O1 . -2.51(15)
C3 C2 N1 C6 . -0.48(18)
C1 C2 N1 C6 . 178.18(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139087647
