#------------------------------------------------------------------------------
#$Date: 2022-03-29 04:36:38 +0300 (Tue, 29 Mar 2022) $
#$Revision: 274056 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/89/2108956.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_2108956
loop_
_publ_author_name
'Pal, Rumpa'
'Jelsch, Christian'
'Momma, Koichi'
'Grabowsky, Simon'
_publ_contact_author
;
Dr. Christian Jelsch
Director of Research CNRS
CRM2   University of Lorraine
Nancy 54000 France
;
_publ_section_title
;
 π-Hole bonding in a new co-crystal hydrate of gallic acid and pyrazine:
 static and dynamic charge density analysis
;
_journal_coeditor_code           PX5047SUP1
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520622001457
_journal_volume                  78
_journal_year                    2022
_chemical_formula_moiety         '4(C7 H6 O5), (C4 H4 N2), 4(H2 O)'
_chemical_formula_sum            'C32 H36 N2 O24'
_chemical_formula_weight         832.60
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'MoPro v21.06'
_cell_angle_alpha                92.440(4)
_cell_angle_beta                 96.223(4)
_cell_angle_gamma                112.469(3)
_cell_formula_units_Z            1
_cell_length_a                   7.7242(8)
_cell_length_b                   9.00420(10)
_cell_length_c                   13.37690(10)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.95
_cell_measurement_theta_min      19.86
_cell_volume                     851.09(9)
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.02127
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14250
_diffrn_reflns_theta_full        45.33
_diffrn_reflns_theta_max         45.33
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.99295
_exptl_absorpt_correction_T_min  0.98473
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;   
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             434
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.333
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     816
_refine_ls_number_reflns         13688
_refine_ls_number_restraints     543
_refine_ls_restrained_S_all      2.573
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0227
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0284
_refine_ls_wR_factor_ref         0.0292
_reflns_number_gt                11776
_reflns_number_total             13688
_reflns_threshold_expression     'I > 2 σ(I)'
_cod_data_source_file            px5047sup1.cif
_cod_data_source_block           I
_cod_database_code               2108956
loop_
_symmetry_equiv_pos_as_xyz
' x , y , z '
' -x , -y , -z '
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_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
O O4 0.93098(4) 0.17536(3) 0.12490(2) 0.01184(3) Uani 1 d . . . .
O O9 0.30578(4) 0.66851(3) 1.06798(2) 0.01000(3) Uani 1 d . . . .
O O5 1.07366(4) 0.48216(3) 0.210905(19) 0.00966(2) Uani 1 d . . . .
O O8 0.10292(4) 0.36156(3) 0.98185(2) 0.01002(3) Uani 1 d . . . .
O O6 0.44754(3) 0.31498(2) 0.680958(14) 0.01100(2) Uani 1 d . . . .
O O7 0.61028(4) 0.57584(3) 0.66235(2) 0.01020(3) Uani 1 d . . . .
O O11 -0.08850(3) 0.06525(3) 0.890464(18) 0.01212(3) Uani 1 d . . . .
O O10 0.60252(4) 0.87472(3) 0.98202(2) 0.01278(3) Uani 1 d . . . .
O O3 0.65783(5) -0.06065(3) 0.19595(2) 0.01435(3) Uani 1 d . . . .
O O1 0.53562(5) 0.20105(4) 0.51146(2) 0.01321(3) Uani 1 d . . . .
O O12 1.19272(4) 0.78543(3) 0.278173(18) 0.01483(3) Uani 1 d . . . .
O O2 0.72600(3) 0.46126(2) 0.513695(15) 0.01363(2) Uani 1 d . . . .
N N1 1.04546(5) 0.91265(4) 0.42593(3) 0.01598(3) Uani 1 d . . . .
C C11 0.24945(4) 0.45773(3) 0.935670(19) 0.00694(2) Uani 1 d . . . .
C C6 0.93833(4) 0.37008(3) 0.25550(2) 0.00731(3) Uani 1 d . . . .
C C13 0.50030(4) 0.72159(3) 0.93796(2) 0.00775(3) Uani 1 d . . . .
C C1 0.66389(4) 0.32112(3) 0.474020(19) 0.00836(3) Uani 1 d . . . .
C C10 0.29958(4) 0.40665(3) 0.84801(2) 0.00761(3) Uani 1 d . . . .
H H10 0.2218(6) 0.2852(4) 0.8132(3) 0.02394 Uani 1 d D U . .
C C8 0.50175(4) 0.45992(3) 0.711461(19) 0.00750(3) Uani 1 d . . . .
C C9 0.44880(4) 0.51512(3) 0.804362(19) 0.00709(3) Uani 1 d . . . .
C C3 0.65437(4) 0.12095(3) 0.33517(2) 0.00879(3) Uani 1 d . . . .
H H3 0.5439(6) 0.0259(4) 0.3651(3) 0.02633 Uani 1 d D U . .
C C14 0.54845(4) 0.67289(3) 0.84868(2) 0.00809(3) Uani 1 d . . . .
H H14 0.6635(5) 0.7555(5) 0.8144(3) 0.02490 Uani 1 d D U . .
C C4 0.72306(4) 0.08822(3) 0.24839(2) 0.00880(3) Uani 1 d . . . .
C C2 0.73029(4) 0.27889(3) 0.381960(19) 0.00761(3) Uani 1 d . . . .
C C12 0.34910(4) 0.61519(3) 0.981538(19) 0.00700(3) Uani 1 d . . . .
C C5 0.86550(4) 0.21195(3) 0.20911(2) 0.00806(3) Uani 1 d . . . .
C C7 0.87096(4) 0.40333(3) 0.34232(2) 0.00808(3) Uani 1 d . . . .
H H7 0.9276(6) 0.5243(4) 0.3795(3) 0.02404 Uani 1 d D U . .
C C15 0.94229(5) 0.83963(4) 0.49692(3) 0.01680(4) Uani 1 d . . . .
H H15 0.8957(7) 0.7100(3) 0.4949(4) 0.02201 Uani 1 d D U . .
C C16 1.10301(5) 1.07310(4) 0.42915(3) 0.01583(4) Uani 1 d . . . .
H H16 1.1883(7) 1.1339(6) 0.3728(3) 0.02719 Uani 1 d D U . .
H H11A -0.1919(6) 0.0065(6) 0.9282(4) 0.02720 Uani 1 d D U . .
H H4 1.0147(7) 0.2758(4) 0.1015(4) 0.02134 Uani 1 d D U . .
H H9 0.2001(6) 0.5796(5) 1.0888(4) 0.02032 Uani 1 d D U . .
H H5 1.1080(8) 0.5901(4) 0.2442(4) 0.02113 Uani 1 d D U . .
H H10O 0.5807(9) 0.8836(7) 1.0521(2) 0.02302 Uani 1 d D U . .
H H7O 0.6477(8) 0.5228(6) 0.6046(3) 0.02056 Uani 1 d D U . .
H H8 0.0409(8) 0.2558(4) 0.9437(4) 0.02076 Uani 1 d D U . .
H H12B 1.1761(8) 0.8461(6) 0.2214(3) 0.02692 Uani 1 d D U . .
H H1 0.5078(8) 0.2479(6) 0.5753(3) 0.02106 Uani 1 d D U . .
H H11B -0.0224(7) -0.0077(6) 0.8846(4) 0.02716 Uani 1 d D U . .
H H3O 0.5926(8) -0.1435(6) 0.2390(4) 0.02540 Uani 1 d D U . .
H H12A 1.1384(8) 0.8239(7) 0.3316(3) 0.02665 Uani 1 d D U . .
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 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
H H 0.0000 0.0000 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
N N 0.0061 0.0033 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
O O 0.0106 0.0060 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O4 H4 108.5(3) . . . ?
C12 O9 H9 107.8(3) . . . ?
C6 O5 H5 110.9(3) . . . ?
C11 O8 H8 110.0(3) . . . ?
C8 O7 H7O 107.4(3) . . . ?
H11A O11 H11B 103.2(5) . . . ?
C13 O10 H10O 110.5(3) . . . ?
C4 O3 H3O 109.8(3) . . . ?
C1 O1 H1 106.9(3) . . . ?
H12B O12 H12A 103.6(5) . . . ?
C15 N1 C16 117.00(3) . . . ?
O8 C11 C12 116.13(2) . . . ?
O8 C11 C10 123.20(2) . . . ?
C12 C11 C10 120.67(2) . . . ?
O5 C6 C5 116.31(2) . . . ?
O5 C6 C7 124.20(2) . . . ?
C5 C6 C7 119.50(2) . . . ?
O10 C13 C12 120.80(2) . . . ?
O10 C13 C14 118.90(2) . . . ?
C12 C13 C14 120.30(2) . . . ?
O1 C1 O2 122.24(2) . . . ?
O1 C1 C2 116.12(2) . . . ?
O2 C1 C2 121.64(2) . . . ?
C11 C10 C9 119.24(2) . . . ?
C11 C10 H10 120.1(2) . . . ?
C9 C10 H10 120.6(2) . . . ?
O7 C8 O6 122.17(2) . . . ?
O7 C8 C9 115.00(2) . . . ?
O6 C8 C9 122.83(2) . . . ?
C8 C9 C14 120.27(2) . . . ?
C8 C9 C10 118.96(2) . . . ?
C14 C9 C10 120.76(2) . . . ?
C4 C3 C2 118.81(2) . . . ?
C4 C3 H3 120.2(2) . . . ?
C2 C3 H3 121.0(2) . . . ?
C13 C14 C9 119.54(2) . . . ?
C13 C14 H14 120.3(2) . . . ?
C9 C14 H14 120.1(2) . . . ?
O3 C4 C5 116.07(2) . . . ?
O3 C4 C3 123.78(2) . . . ?
C5 C4 C3 120.14(2) . . . ?
C1 C2 C7 117.32(2) . . . ?
C1 C2 C3 121.41(2) . . . ?
C7 C2 C3 121.27(2) . . . ?
O9 C12 C13 118.26(2) . . . ?
O9 C12 C11 122.28(2) . . . ?
C13 C12 C11 119.45(2) . . . ?
O4 C5 C6 120.77(2) . . . ?
O4 C5 C4 118.61(2) . . . ?
C6 C5 C4 120.62(2) . . . ?
C6 C7 C2 119.65(2) . . . ?
C6 C7 H7 120.2(2) . . . ?
C2 C7 H7 120.2(2) . . . ?
N1 C15 C16 121.43(3) . . 2_776 ?
N1 C15 H15 117.4(3) . . . ?
C16 C15 H15 121.2(3) 2_776 . . ?
N1 C16 C15 121.57(3) . . 2_776 ?
N1 C16 H16 117.8(3) . . . ?
C15 C16 H16 120.7(3) 2_776 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C5 1.3611(4) . ?
O4 H4 0.977(3) . ?
O9 C12 1.3561(4) . ?
O9 H9 0.976(3) . ?
O5 C6 1.3591(4) . ?
O5 H5 0.977(3) . ?
O8 C11 1.3639(4) . ?
O8 H8 0.976(3) . ?
O6 C8 1.2429(3) . ?
O7 C8 1.3163(4) . ?
O7 H7O 1.015(3) . ?
O11 H11A 0.979(3) . ?
O11 H11B 0.980(3) . ?
O10 C13 1.3674(4) . ?
O10 H10O 0.976(3) . ?
O3 C4 1.3675(4) . ?
O3 H3O 0.976(3) . ?
O1 C1 1.3177(4) . ?
O1 H1 1.016(3) . ?
O12 H12B 0.979(3) . ?
O12 H12A 0.981(3) . ?
O2 C1 1.2366(3) . ?
N1 C15 1.3364(5) . ?
N1 C16 1.3365(4) . ?
C11 C12 1.4031(4) . ?
C11 C10 1.3875(4) . ?
C6 C5 1.4020(4) . ?
C6 C7 1.3891(4) . ?
C13 C12 1.4005(4) . ?
C13 C14 1.3905(4) . ?
C1 C2 1.4732(4) . ?
C10 C9 1.3990(4) . ?
C10 H10 1.081(3) . ?
C8 C9 1.4737(4) . ?
C9 C14 1.3984(4) . ?
C3 C4 1.3927(4) . ?
C3 C2 1.4019(4) . ?
C3 H3 1.080(3) . ?
C14 H14 1.079(3) . ?
C4 C5 1.4021(4) . ?
C2 C7 1.4008(4) . ?
C7 H7 1.080(3) . ?
C15 C16 1.3918(5) 2_776 ?
C15 H15 1.080(3) . ?
C16 C15 1.3918(5) 2_776 ?
C16 H16 1.081(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O11 H11A O10 0.979(3) 1.825(3) 2.7968(5) 171.44(11) 1_445
O9 H9 O5 0.976(3) 2.051(4) 2.8987(4) 144.1(2) 1_456
C15 H15 O2 1.080(3) 2.162(3) 3.2006(4) 160.58(18) 1
O4 H4 O5 0.977(3) 2.186(5) 2.7013(4) 111.5(3) 1
O9 H9 O8 0.976(3) 2.206(5) 2.7293(4) 112.2(3) 1
O5 H5 O12 0.977(3) 1.648(3) 2.6084(4) 166.87(17) 1
O10 H10O O9 0.976(3) 2.301(6) 2.7429(5) 106.5(4) 1
O7 H7O O2 1.015(3) 1.584(3) 2.5948(4) 172.88(12) 1
O7 H7O C1 1.015(3) 2.513(3) 3.4984(4) 163.51(15) 1
O8 H8 O11 0.976(3) 1.697(3) 2.6672(4) 171.60(12) 1
O1 H1 O6 1.016(3) 1.692(3) 2.7067(4) 176.12(6) 1
O1 H1 C8 1.016(3) 2.599(3) 3.5702(4) 159.95(17) 1
O12 H12A N1 0.981(3) 1.815(3) 2.7935(5) 174.84(7) 1
O12 H12A C16 0.981(3) 2.666(4) 3.5352(5) 147.8(2) 1
O10 H10O O3 0.976(3) 1.936(4) 2.8485(4) 154.5(3) 1_566
O4 H4 O8 0.977(3) 1.888(4) 2.7127(4) 140.4(2) 1_654
C10 H10 O3 1.081(3) 2.531(4) 3.2908(4) 126.5(2) 2_656
C3 H3 O1 1.080(3) 2.613(4) 3.5603(5) 146.1(2) 2_656
O11 H11B O4 0.980(3) 1.900(3) 2.8719(4) 171.05(10) 2_656
O3 H3O O6 0.976(3) 1.864(3) 2.7937(3) 158.1(3) 2_656
O12 H12B O11 0.979(3) 1.905(3) 2.8699(4) 167.80(14) 2_666
C16 H16 O7 1.081(3) 2.575(4) 3.4585(5) 138.4(2) 2_776
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
O4 C5 C6 O5 . . . . 0.87(3) ?
O4 C5 C6 C7 . . . . -178.95(3) ?
O4 C5 C4 O3 . . . . -1.62(3) ?
O4 C5 C4 C3 . . . . 179.22(3) ?
O9 C12 C13 O10 . . . . 0.59(3) ?
O9 C12 C13 C14 . . . . -179.22(3) ?
O9 C12 C11 O8 . . . . 1.40(3) ?
O9 C12 C11 C10 . . . . -179.05(3) ?
O5 C6 C5 C4 . . . . -178.89(3) ?
O5 C6 C7 C2 . . . . 179.71(3) ?
O5 C6 C7 H7 . . . . -0.8(2) ?
O8 C11 C12 C13 . . . . -179.39(3) ?
O8 C11 C10 C9 . . . . 178.25(3) ?
O8 C11 C10 H10 . . . . -0.4(2) ?
O6 C8 O7 H7O . . . . -6.2(3) ?
O6 C8 C9 C14 . . . . 164.13(3) ?
O6 C8 C9 C10 . . . . -14.94(3) ?
O7 C8 C9 C14 . . . . -16.30(3) ?
O7 C8 C9 C10 . . . . 164.62(3) ?
O10 C13 C12 C11 . . . . -178.66(3) ?
O10 C13 C14 C9 . . . . 178.11(3) ?
O10 C13 C14 H14 . . . . -0.8(3) ?
O3 C4 C5 C6 . . . . 178.15(3) ?
O3 C4 C3 C2 . . . . -179.15(3) ?
O3 C4 C3 H3 . . . . 0.4(3) ?
O1 C1 C2 C7 . . . . -178.06(3) ?
O1 C1 C2 C3 . . . . 2.65(4) ?
O2 C1 O1 H1 . . . . -1.7(3) ?
O2 C1 C2 C7 . . . . 1.69(3) ?
O2 C1 C2 C3 . . . . -177.60(3) ?
C11 C12 O9 H9 . . . . 0.5(3) ?
C11 C12 C13 C14 . . . . 1.53(3) ?
C11 C10 C9 C8 . . . . 179.78(3) ?
C11 C10 C9 C14 . . . . 0.72(3) ?
C6 C5 O4 H4 . . . . -8.1(3) ?
C6 C5 C4 C3 . . . . -1.01(3) ?
C6 C7 C2 C1 . . . . -179.88(3) ?
C6 C7 C2 C3 . . . . -0.59(3) ?
C13 C12 O9 H9 . . . . -178.8(3) ?
C13 C12 C11 C10 . . . . 0.17(3) ?
C13 C14 C9 C8 . . . . -178.10(3) ?
C13 C14 C9 C10 . . . . 0.95(3) ?
C1 C2 C7 H7 . . . . 0.6(2) ?
C1 C2 C3 C4 . . . . -179.89(3) ?
C1 C2 C3 H3 . . . . 0.6(3) ?
C10 C11 O8 H8 . . . . -0.8(3) ?
C10 C9 C14 H14 . . . . 179.9(3) ?
H10 C10 C11 C12 . . . . -179.9(3) ?
H10 C10 C9 C8 . . . . -1.6(3) ?
H10 C10 C9 C14 . . . . 179.4(3) ?
C8 C9 C14 H14 . . . . 0.8(3) ?
C9 C8 O7 H7O . . . . 174.2(3) ?
C9 C14 C13 C12 . . . . -2.08(3) ?
C9 C10 C11 C12 . . . . -1.28(3) ?
C3 C4 O3 H3O . . . . -19.4(3) ?
C3 C2 C7 H7 . . . . 179.9(2) ?
H3 C3 C4 C5 . . . . 179.5(3) ?
H3 C3 C2 C7 . . . . -178.7(3) ?
C14 C13 O10 H10O . . . . -163.3(3) ?
H14 C14 C13 C12 . . . . 179.0(3) ?
C4 C5 O4 H4 . . . . 171.6(3) ?
C4 C5 C6 C7 . . . . 1.28(3) ?
C4 C3 C2 C7 . . . . 0.85(3) ?
C2 C1 O1 H1 . . . . 178.1(3) ?
C2 C7 C6 C5 . . . . -0.48(3) ?
C2 C3 C4 C5 . . . . -0.05(3) ?
C12 C13 O10 H10O . . . . 16.9(3) ?
C12 C11 O8 H8 . . . . 178.7(3) ?
C5 C6 O5 H5 . . . . 174.8(3) ?
C5 C6 C7 H7 . . . . 179.0(2) ?
C5 C4 O3 H3O . . . . 161.4(3) ?
C7 C6 O5 H5 . . . . -5.4(3) ?
C15 N1 C16 H16 . . . . 179.1(3) ?
H15 C15 N1 C16 . . . . -179.8(3) ?

_cod_database_fobs_code 2108956
