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#$Date: 2022-06-23 12:26:01 +0300 (Thu, 23 Jun 2022) $
#$Revision: 276187 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105481.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_8105481
loop_
_publ_author_name
'Dai, Bencai'
'Zhou, Yang'
'Chen, Jin'
'Liu, Changchun'
'Shen, Zhihao'
'Tang, Junming'
_publ_section_title
;
 The crystal structure of 2,4-dihydroxybenzoic
 acid--nicotinamide--methanol (1/1/1), C15H18N2O6
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1413
_journal_page_last               1415
_journal_paper_doi               10.1515/ncrs-2020-0341
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C2 H6 O, C6 H6 N2 O, C7 H6 O4'
_chemical_formula_sum            'C15 H18 N2 O6'
_chemical_formula_weight         322.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                79.223(2)
_cell_angle_beta                 82.086(3)
_cell_angle_gamma                65.182(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4217(18)
_cell_length_b                   7.7021(18)
_cell_length_c                   15.362(4)
_cell_measurement_reflns_used    2094
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.33
_cell_measurement_theta_min      3.262
_cell_volume                     781.2(3)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 2009 [1])'
_computing_data_reduction        'SAINT v7.34A (Bruker, 2009[1])'
_computing_molecular_graphics    'Diamond (Brandenburg, et al., 2012 [5])'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009[4])'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008 [2])'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015 [3])'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5984
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.705
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.9442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2887
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0444
_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)+(0.0668P)²+0.1822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1341
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2225
_reflns_number_total             2887
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0341_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105481
_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_max   0.972
_shelx_estimated_absorpt_t_min   0.956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O6-C14 = O6-C14'
 1.47 with sigma of 0.01
 C14-C15 = C14'-C15'
 1.52 with sigma of 0.01
 C15-O6 = C15'-O6
 2.41 with sigma of 0.02
3. Rigid bond restraints
 O6, C14, C15, C14', C15'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(O6) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14')
\\sim Ueq, Uanis(C15') \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
5. Others
 Sof(C14')=Sof(H14C)=Sof(H14D)=Sof(C15')=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
6.a Riding coordinates:
 O6(H6)
6.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14'(H14C,H14D)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4A), C5(H5A), C9(H9), C11(H11), C12(H12)
6.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
6.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C15'(H15D,H15E,H15F)
6.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O5(H5)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8679(3) 0.5277(3) 0.71896(11) 0.0427(4) Uani 1 1 d . . . . .
H1 H 0.9264 0.3957 0.7388 0.051 Uiso 1 1 calc R . . . .
C2 C 0.8508(3) 0.6550(3) 0.77568(11) 0.0413(4) Uani 1 1 d . . . . .
C3 C 0.7657(3) 0.8516(3) 0.74504(12) 0.0480(4) Uani 1 1 d . . . . .
H3 H 0.7501 0.9410 0.7817 0.058 Uiso 1 1 calc R . . . .
C4 C 0.7045(3) 0.9128(3) 0.65966(12) 0.0501(5) Uani 1 1 d . . . . .
H4A H 0.6507 1.0437 0.6372 0.060 Uiso 1 1 calc R . . . .
C5 C 0.7248(3) 0.7761(3) 0.60848(11) 0.0469(4) Uani 1 1 d . . . . .
H5A H 0.6812 0.8179 0.5513 0.056 Uiso 1 1 calc R . . . .
C6 C 0.9141(3) 0.5864(3) 0.86878(11) 0.0475(4) Uani 1 1 d . . . . .
C7 C 0.7387(2) 0.3156(2) 0.39116(10) 0.0373(4) Uani 1 1 d . . . . .
C8 C 0.6794(2) 0.3947(2) 0.30447(11) 0.0386(4) Uani 1 1 d . . . . .
C9 C 0.6861(3) 0.2763(2) 0.24520(11) 0.0424(4) Uani 1 1 d . . . . .
H9 H 0.6472 0.3294 0.1878 0.051 Uiso 1 1 calc R . . . .
C10 C 0.7509(3) 0.0789(3) 0.27166(12) 0.0440(4) Uani 1 1 d . . . . .
C11 C 0.8093(3) -0.0019(3) 0.35758(12) 0.0477(4) Uani 1 1 d . . . . .
H11 H 0.8524 -0.1344 0.3754 0.057 Uiso 1 1 calc R . . . .
C12 C 0.8025(3) 0.1164(3) 0.41530(12) 0.0441(4) Uani 1 1 d . . . . .
H12 H 0.8417 0.0621 0.4726 0.053 Uiso 1 1 calc R . . . .
C13 C 0.7363(2) 0.4415(3) 0.45270(11) 0.0408(4) Uani 1 1 d . . . . .
C14 C 0.7028(9) 0.1979(11) 0.9960(3) 0.141(2) Uani 0.746(8) 1 d D U P A 1
H14A H 0.7093 0.3129 1.0098 0.169 Uiso 0.746(8) 1 calc R . P A 1
H14B H 0.8375 0.0991 0.9954 0.169 Uiso 0.746(8) 1 calc R . P A 1
C14' C 0.6282(19) 0.148(2) 0.9723(6) 0.092(4) Uani 0.254(8) 1 d D U P A 2
H14C H 0.5281 0.2674 0.9451 0.110 Uiso 0.254(8) 1 calc R . P A 2
H14D H 0.6130 0.0418 0.9534 0.110 Uiso 0.254(8) 1 calc R . P A 2
C15 C 0.6427(11) 0.2394(9) 0.9120(3) 0.138(2) Uani 0.746(8) 1 d D U P A 1
H15A H 0.5635 0.1703 0.9075 0.207 Uiso 0.746(8) 1 calc GR . P A 1
H15B H 0.7572 0.2015 0.8708 0.207 Uiso 0.746(8) 1 calc GR . P A 1
H15C H 0.5651 0.3758 0.8985 0.207 Uiso 0.746(8) 1 calc GR . P A 1
C15' C 0.825(2) 0.142(4) 0.9401(13) 0.181(9) Uani 0.254(8) 1 d D U P A 2
H15D H 0.8747 0.1854 0.9826 0.271 Uiso 0.254(8) 1 calc GR . P A 2
H15E H 0.8158 0.2252 0.8844 0.271 Uiso 0.254(8) 1 calc GR . P A 2
H15F H 0.9142 0.0122 0.9323 0.271 Uiso 0.254(8) 1 calc GR . P A 2
N1 N 1.0752(2) 0.4266(2) 0.88331(10) 0.0580(5) Uani 1 1 d . . . . .
H1A H 1.1148 0.3834 0.9362 0.070 Uiso 1 1 calc R . . . .
H1B H 1.1408 0.3653 0.8399 0.070 Uiso 1 1 calc R . . . .
N2 N 0.8040(2) 0.5862(2) 0.63687(9) 0.0435(4) Uani 1 1 d . . . . .
O1 O 0.8151(2) 0.6792(2) 0.92925(8) 0.0694(5) Uani 1 1 d . . . . .
O2 O 0.8033(2) 0.35151(19) 0.53040(8) 0.0560(4) Uani 1 1 d . . . . .
H2 H 0.7950 0.4307 0.5615 0.084 Uiso 1 1 calc GR . . . .
O3 O 0.6785(2) 0.61795(18) 0.43230(8) 0.0526(4) Uani 1 1 d . . . . .
O4 O 0.6182(2) 0.58690(17) 0.27520(8) 0.0531(4) Uani 1 1 d . . . . .
H4 H 0.6095 0.6438 0.3167 0.080 Uiso 1 1 calc GR . . . .
O5 O 0.7605(2) -0.04366(19) 0.21642(9) 0.0605(4) Uani 1 1 d . . . . .
H5 H 0.7058 0.0189 0.1710 0.091 Uiso 1 1 calc GR . . . .
O6 O 0.5927(3) 0.1356(3) 1.06639(11) 0.0925(6) Uani 1 1 d D U . . .
H6 H 0.4744 0.1931 1.0571 0.139 Uiso 1 1 d R . . A .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
H14A C14 H14B 106.9 . .
C15 C14 H14A 107.4 . .
C15 C14 H14B 107.4 . .
C15 C14 O6 119.8(6) . .
O6 C14 H14A 107.4 . .
O6 C14 H14B 107.4 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
H14C C14' H14D 107.7 . .
C15' C14' H14C 108.8 . .
C15' C14' H14D 108.8 . .
O6 C14' H14C 108.8 . .
O6 C14' H14D 108.8 . .
O6 C14' C15' 113.9(11) . .
C14' C15' H15D 109.5 . .
C14' C15' H15E 109.5 . .
C14' C15' H15F 109.5 . .
H15D C15' H15E 109.5 . .
H15D C15' H15F 109.5 . .
H15E C15' H15F 109.5 . .
C2 C1 H1 118.5 . .
N2 C1 H1 118.5 . .
N2 C1 C2 122.92(17) . .
C1 C2 C3 118.13(16) . .
C1 C2 C6 121.94(16) . .
C3 C2 C6 119.89(16) . .
C2 C3 H3 120.4 . .
C4 C3 C2 119.26(17) . .
C4 C3 H3 120.4 . .
C3 C4 H4A 120.7 . .
C5 C4 C3 118.58(17) . .
C5 C4 H4A 120.7 . .
C4 C5 H5A 118.4 . .
N2 C5 C4 123.24(16) . .
N2 C5 H5A 118.4 . .
N1 C6 C2 117.94(15) . .
O1 C6 C2 119.93(17) . .
O1 C6 N1 122.13(16) . .
C8 C7 C13 120.01(15) . .
C12 C7 C8 117.98(15) . .
C12 C7 C13 121.99(15) . .
C9 C8 C7 120.40(15) . .
O4 C8 C7 121.71(15) . .
O4 C8 C9 117.87(15) . .
C8 C9 H9 120.1 . .
C10 C9 C8 119.89(16) . .
C10 C9 H9 120.1 . .
C9 C10 C11 120.44(16) . .
O5 C10 C9 122.35(16) . .
O5 C10 C11 117.21(16) . .
C10 C11 H11 120.5 . .
C12 C11 C10 119.09(16) . .
C12 C11 H11 120.5 . .
C7 C12 H12 118.9 . .
C11 C12 C7 122.20(16) . .
C11 C12 H12 118.9 . .
O2 C13 C7 114.91(15) . .
O3 C13 C7 122.51(15) . .
O3 C13 O2 122.58(15) . .
C6 N1 H1A 120.0 . .
C6 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C5 N2 C1 117.83(15) . .
C13 O2 H2 109.5 . .
C8 O4 H4 109.5 . .
C10 O5 H5 109.5 . .
C14 O6 H6 108.5 . .
C14' O6 H6 86.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 C15 1.360(6) .
C14 O6 1.399(5) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C14' H14C 0.9700 .
C14' H14D 0.9700 .
C14' C15' 1.462(10) .
C14' O6 1.425(8) .
C15' H15D 0.9600 .
C15' H15E 0.9600 .
C15' H15F 0.9600 .
C1 H1 0.9300 .
C1 C2 1.386(2) .
C1 N2 1.338(2) .
C2 C3 1.388(3) .
C2 C6 1.496(2) .
C3 H3 0.9300 .
C3 C4 1.379(3) .
C4 H4A 0.9300 .
C4 C5 1.376(3) .
C5 H5A 0.9300 .
C5 N2 1.336(2) .
C6 N1 1.315(2) .
C6 O1 1.238(2) .
C7 C8 1.404(2) .
C7 C12 1.393(2) .
C7 C13 1.469(2) .
C8 C9 1.387(2) .
C8 O4 1.357(2) .
C9 H9 0.9300 .
C9 C10 1.385(2) .
C10 C11 1.393(3) .
C10 O5 1.357(2) .
C11 H11 0.9300 .
C11 C12 1.367(3) .
C12 H12 0.9300 .
C13 O2 1.310(2) .
C13 O3 1.232(2) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
O2 H2 0.8200 .
O4 H4 0.8200 .
O5 H5 0.8200 .
O6 H6 0.8200 .
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
N1 H1A O1 0.86 2.12 2.971(2) 171.2 2_767
N1 H1B O4 0.86 2.43 3.081(2) 133.0 2_766
N1 H1B O5 0.86 2.55 3.269(2) 141.2 2_756
O2 H2 N2 0.82 1.84 2.657(2) 173.1 .
O4 H4 O3 0.82 1.87 2.5854(18) 145.6 .
O5 H5 O6 0.82 1.81 2.631(2) 174.5 1_554
O6 H6 O1 0.82 1.95 2.749(3) 164.2 2_667
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 C2 C3 C4 -1.0(3) . . . .
C1 C2 C6 N1 37.9(3) . . . .
C1 C2 C6 O1 -141.8(2) . . . .
C2 C1 N2 C5 1.6(3) . . . .
C2 C3 C4 C5 1.9(3) . . . .
C3 C2 C6 N1 -144.43(19) . . . .
C3 C2 C6 O1 35.8(3) . . . .
C3 C4 C5 N2 -1.1(3) . . . .
C4 C5 N2 C1 -0.6(3) . . . .
C6 C2 C3 C4 -178.74(17) . . . .
C7 C8 C9 C10 0.3(3) . . . .
C8 C7 C12 C11 0.2(3) . . . .
C8 C7 C13 O2 -176.95(15) . . . .
C8 C7 C13 O3 2.1(3) . . . .
C8 C9 C10 C11 0.0(3) . . . .
C8 C9 C10 O5 179.98(16) . . . .
C9 C10 C11 C12 -0.2(3) . . . .
C10 C11 C12 C7 0.1(3) . . . .
C12 C7 C8 C9 -0.4(2) . . . .
C12 C7 C8 O4 -178.95(15) . . . .
C12 C7 C13 O2 1.7(2) . . . .
C12 C7 C13 O3 -179.31(16) . . . .
C13 C7 C8 C9 178.27(15) . . . .
C13 C7 C8 O4 -0.3(2) . . . .
C13 C7 C12 C11 -178.42(16) . . . .
N2 C1 C2 C3 -0.8(3) . . . .
N2 C1 C2 C6 176.88(16) . . . .
O4 C8 C9 C10 178.88(16) . . . .
O5 C10 C11 C12 179.84(16) . . . .
