##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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##############################################################################
data_I
_audit_creation_method     'SHELXL-2014/7'
_database_code_depnum_ccdc_archive     'CCDC 1423138'
_chemical_name_systematic
;
Tetrakis(1-oxidopyridin-2-yl)methane methanol tetrasolvate
;
_chemical_name_common
       'Tetrakis(pyridin-2-yl)methane tetraN-oxide methanol tetrasolvate'
_chemical_formula_moiety     'C21 H16 N4 O4, 4(C H4 O)'
_chemical_formula_sum     'C25 H32 N4 O8'
_chemical_formula_iupac     'C21 H16 N4 O4, 4C H4 O'
_chemical_formula_weight     516.54
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     tetragonal
_space_group_name_H-M_alt     'I 41/a'
_space_group_name_Hall     '-I 4ad'
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'
_cell_length_a     14.4474(4)
_cell_length_b     14.4474(4)
_cell_length_c     12.2965(5)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2566.62(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9662
_cell_measurement_theta_min     3.6
_cell_measurement_theta_max     27.4
_cell_measurement_temperature     200(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.2
_exptl_crystal_size_mid     0.2
_exptl_crystal_size_min     0.1
_exptl_crystal_density_diffrn     1.337
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1096
_exptl_absorpt_coefficient_mu     0.10
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_shelx_estimated_absorpt_T_min     0.980
_shelx_estimated_absorpt_T_max     0.990
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     200(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type     'Rigaku R-AXIS RAPID'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.00
_diffrn_reflns_number     12321
_diffrn_reflns_av_R_equivalents     0.0310
_diffrn_reflns_theta_min     3.6
_diffrn_reflns_theta_max     27.4
_diffrn_reflns_theta_full     25.2
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
Refinement was performed using all reflections. The weighted R-factor
(wR) and goodness of fit (S) are based on F².
R-factor (gt) are based on F. The threshold expression of
F² > 2.0 σ(F²) is used only for calculating R-factor
(gt).
;
_reflns_number_total     1470
_reflns_number_gt     1289
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.053
_refine_ls_R_factor_gt     0.049
_refine_ls_wR_factor_gt     0.134
_refine_ls_wR_factor_ref     0.138
_refine_ls_goodness_of_fit_ref     1.07
_refine_ls_restrained_S_all     1.07
_refine_ls_number_reflns     1470
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0821P)²+1.7364P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.400
_refine_diff_density_min     -0.253
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_cell_refinement
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_data_reduction
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_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)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    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 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    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_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
    _geom_angle_publ_flag
    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_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_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    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_
    _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
data_Global
_journal_date_recd_electronic     2015-08-31
_journal_date_accepted     2015-09-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue     10
_journal_page_first     o754
_journal_page_last     o755
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989015016862
_journal_coeditor_code     IS5417
_publ_contact_author_name     'Matsumoto, Kouzou'
_publ_contact_author_address
;
Institute of Natural Sciences
Senshu University
Higashimita 2-1-1
Kawasaki
Kanagawa 214-8580
Japan
;
_publ_contact_author_email     'matsumoto@isc.senshu-u.ac.jp'
_publ_contact_author_fax     '+81-44-911-7254'
_publ_contact_author_phone     '+81-44-911-1223'
_publ_section_title
;
Crystal structure of tetrakis(1-oxidopyridin-2-yl)methane methanol tetrasolvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Matsumoto, Kouzou'
;
Institute of Natural Sciences
Senshu University
Higashimita 2-1-1
Kawasaki
Kanagawa 214-8580
Japan
;
    'Kawashita, Kazuaki'
;
Department of Chemistry
Graduate School of Science
Osaka University
Toyonaka
Osaka 560-0043
Japan
;
    'Kannami, Masaki'
;
Department of Chemistry
Graduate School of Science
Osaka University
Toyonaka
Osaka 560-0043
Japan
;
    'Oda, Masaji'
;
Department of Chemistry
Graduate School of Science
Osaka University
Toyonaka
Osaka 560-0043
Japan
;
