#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:10:38 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281416 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/60/7246035.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_7246035
loop_
_publ_author_name
'Iqbal, Infal'
'Mehmood, Arshad'
'Noureen, Sajida'
'Lecomte, Claude'
'Ahmed, Maqsood'
_publ_section_title
;
 Crystal engineering, electron density analysis, and in situ variable
 temperature studies on co-crystal between nicotinic acid and gallic acid
 sesquihydrate
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              770
_journal_page_last               784
_journal_paper_doi               10.1039/D2CE01149B
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C7 H6 O5, H2 O'
_chemical_formula_sum            'C7 H8 O6'
_chemical_formula_weight         188.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2022-05-14
_audit_creation_method
;
FinalCif V89 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2022-05-16 deposited with the CCDC.	2022-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.547(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.192(4)
_cell_length_b                   3.6287(9)
_cell_length_c                   15.065(3)
_cell_measurement_reflns_used    1850
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.24
_cell_measurement_theta_min      2.72
_cell_volume                     769.1(3)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'Four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1333
_diffrn_reflns_av_unetI/netI     0.1011
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8594
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.835
_diffrn_reflns_theta_min         2.728
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1044 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.9450.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.0791
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0610P)²+0.2896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1726
_reflns_Friedel_coverage         0.000
_reflns_number_gt                923
_reflns_number_total             1469
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01149b2.cif
_cod_data_source_block           mo_infal_iqbal_gallicacid_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7246035--7246043.cif.
;
_cod_database_code               7246035
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C7(H7)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3), O5(H5), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
_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   0.958
_shelx_estimated_absorpt_t_max   0.993
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cobra Cryo device'
_shelx_res_file
;
TITL mo_Infal_Iqbal_Gallicacid_0m in P2/n #13
    mo_infal_iqbal_gallicacid_0m.res
    created by SHELXL-2018/3 at 16:26:46 on 14-May-2022
REM reset to P2/n #13
CELL 0.71073 14.1915 3.6287 15.0653 90 97.5468 90
ZERR 4 0.0035 0.0009 0.0029 0 0.0073 0
LATT 1
SYMM 0.5-X,+Y,0.5-Z
SFAC C H O
UNIT 28 32 24

L.S. 2
PLAN  5
SIZE 0.05 0.1 0.3
TEMP 0
CONF
BOND
fmap 2 53
acta
MORE -1
BOND $H
REM <olex2.extras>
REM <HklSrc "%.\\mo_Infal_Iqbal_Gallicacid_0m.hkl">
REM </olex2.extras>

WGHT    0.061000    0.289600
FVAR       0.28914
O4    3    0.154361    0.008650    0.343265    11.00000    0.02792    0.05297 =
         0.02183    0.00185    0.00560   -0.01081
AFIX 147
H4    2    0.178000    0.058934    0.297934    11.00000   -1.50000
AFIX   0
O3    3    0.102096   -0.139673    0.504871    11.00000    0.02897    0.04637 =
         0.02629    0.00232    0.00694   -0.01196
AFIX 147
H3    2    0.080334   -0.226510    0.456221    11.00000   -1.50000
AFIX   0
O5    3    0.335279    0.267890    0.328527    11.00000    0.02737    0.05818 =
         0.02042   -0.00032    0.01049   -0.01566
AFIX 147
H5    2    0.388504    0.359588    0.333024    11.00000   -1.50000
AFIX   0
O2    3    0.377793    0.204182    0.730322    11.00000    0.04608    0.07117 =
         0.02120   -0.00267    0.00574   -0.02014
AFIX 147
H2    2    0.415310    0.279970    0.772406    11.00000   -1.50000
AFIX   0
C2    1    0.345345    0.176833    0.573352    11.00000    0.02922    0.02333 =
         0.02586    0.00022    0.00732   -0.00237
C5    1    0.220722    0.061721    0.417386    11.00000    0.02485    0.02225 =
         0.02304    0.00148    0.00526    0.00046

AFIX   6
O6    3   -0.009809   -0.511006    0.368932    11.00000    0.03746    0.05040 =
         0.02754    0.00960    0.01186    0.00058
H6A   2   -0.042743   -0.645011    0.399427    11.00000   -1.50000
H6B   2    0.029340   -0.659378    0.349901    11.00000   -1.50000
AFIX   0

C3    1    0.253699    0.044546    0.578487    11.00000    0.02847    0.02842 =
         0.02050    0.00246    0.00969    0.00095
AFIX  43
H3A   2    0.234005   -0.002681    0.633870    11.00000   -1.20000
AFIX   0
C7    1    0.374506    0.242613    0.489838    11.00000    0.02587    0.02905 =
         0.02770   -0.00040    0.01015   -0.00600
AFIX  43
H7    2    0.436285    0.321111    0.486301    11.00000   -1.20000
AFIX   0
C4    1    0.192946   -0.015124    0.500968    11.00000    0.02143    0.02062 =
         0.02694    0.00308    0.00856   -0.00256
C6    1    0.312194    0.191816    0.412545    11.00000    0.02507    0.02486 =
         0.02191   -0.00010    0.01001   -0.00314
O1    3    0.489771    0.403002    0.652288    11.00000    0.03315    0.06737 =
         0.03327    0.00022    0.00418   -0.01711
C1    1    0.412145    0.269139    0.654407    11.00000    0.03139    0.03070 =
         0.02306    0.00099    0.00617   -0.00301
HKLF 4




REM  mo_Infal_Iqbal_Gallicacid_0m in P2/n #13
REM wR2 = 0.1726, GooF = S = 1.083, Restrained GooF = 1.083 for all data
REM R1 = 0.0791 for 923 Fo > 4sig(Fo) and 0.1281 for all 1469 data
REM 125 parameters refined using 0 restraints

END

WGHT      0.0610      0.2896

REM Highest difference peak  0.240,  deepest hole -0.341,  1-sigma level  0.069
Q1    1   0.2978  0.4407  0.7023  11.00000  0.05    0.24
Q2    1   0.5802  0.1544  0.6940  11.00000  0.05    0.22
Q3    1   0.0386  0.0557  0.4652  11.00000  0.05    0.20
Q4    1   0.3128  0.5466  0.4071  11.00000  0.05    0.20
Q5    1   0.3120  0.3185  0.4463  11.00000  0.05    0.19
;
_shelx_res_checksum              95450
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_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
O4 O 0.15436(18) 0.0087(8) 0.34327(16) 0.0340(7) Uani 1 1 d . . . . .
H4 H 0.178000 0.058934 0.297934 0.051 Uiso 1 1 calc R U . . .
O3 O 0.10210(19) -0.1397(8) 0.50487(16) 0.0336(7) Uani 1 1 d . . . . .
H3 H 0.080334 -0.226510 0.456221 0.050 Uiso 1 1 calc R U . . .
O5 O 0.33528(19) 0.2679(8) 0.32853(15) 0.0347(7) Uani 1 1 d . . . . .
H5 H 0.388504 0.359588 0.333024 0.052 Uiso 1 1 calc R U . . .
O2 O 0.3778(2) 0.2042(9) 0.73032(17) 0.0460(9) Uani 1 1 d . . . . .
H2 H 0.415310 0.279970 0.772406 0.069 Uiso 1 1 calc R U . . .
C2 C 0.3453(3) 0.1768(10) 0.5734(2) 0.0258(9) Uani 1 1 d . . . . .
C5 C 0.2207(3) 0.0617(9) 0.4174(2) 0.0232(9) Uani 1 1 d . . . . .
O6 O -0.0098(2) -0.5110(7) 0.36893(17) 0.0378(8) Uani 1 1 d G . . . .
H6A H -0.042743 -0.645011 0.399427 0.057 Uiso 1 1 d G U . . .
H6B H 0.029340 -0.659378 0.349901 0.057 Uiso 1 1 d G U . . .
C3 C 0.2537(3) 0.0445(10) 0.5785(2) 0.0252(9) Uani 1 1 d . . . . .
H3A H 0.234005 -0.002681 0.633870 0.030 Uiso 1 1 calc R U . . .
C7 C 0.3745(3) 0.2426(10) 0.4898(2) 0.0269(9) Uani 1 1 d . . . . .
H7 H 0.436285 0.321111 0.486301 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1929(3) -0.0151(9) 0.5010(2) 0.0225(8) Uani 1 1 d . . . . .
C6 C 0.3122(3) 0.1918(10) 0.4125(2) 0.0233(9) Uani 1 1 d . . . . .
O1 O 0.4898(2) 0.4030(9) 0.65229(18) 0.0446(9) Uani 1 1 d . . . . .
C1 C 0.4121(3) 0.2691(10) 0.6544(2) 0.0282(9) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O4 0.0279(16) 0.053(2) 0.0218(13) 0.0019(13) 0.0056(12) -0.0108(13)
O3 0.0290(17) 0.0464(18) 0.0263(14) 0.0023(12) 0.0069(13) -0.0120(13)
O5 0.0274(17) 0.058(2) 0.0204(13) -0.0003(13) 0.0105(12) -0.0157(14)
O2 0.046(2) 0.071(2) 0.0212(14) -0.0027(15) 0.0057(14) -0.0201(16)
C2 0.029(2) 0.023(2) 0.0259(19) 0.0002(16) 0.0073(17) -0.0024(17)
C5 0.025(2) 0.022(2) 0.0230(18) 0.0015(15) 0.0053(16) 0.0005(16)
O6 0.0375(19) 0.0504(19) 0.0275(14) 0.0096(14) 0.0119(13) 0.0006(15)
C3 0.028(2) 0.028(2) 0.0205(17) 0.0025(16) 0.0097(16) 0.0009(17)
C7 0.026(2) 0.029(2) 0.0277(19) -0.0004(17) 0.0102(17) -0.0060(17)
C4 0.021(2) 0.021(2) 0.0269(18) 0.0031(16) 0.0086(16) -0.0026(16)
C6 0.025(2) 0.025(2) 0.0219(19) -0.0001(16) 0.0100(17) -0.0031(16)
O1 0.0332(19) 0.067(2) 0.0333(16) 0.0002(14) 0.0042(14) -0.0171(16)
C1 0.031(2) 0.031(2) 0.0231(19) 0.0010(17) 0.0062(17) -0.0030(18)
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'
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
_geom_angle_publ_flag
C5 O4 H4 109.5 . . ?
C4 O3 H3 109.5 . . ?
C6 O5 H5 109.5 . . ?
C1 O2 H2 109.5 . . ?
C3 C2 C1 122.1(3) . . ?
C7 C2 C3 119.8(3) . . ?
C7 C2 C1 118.1(3) . . ?
O4 C5 C4 117.4(3) . . ?
O4 C5 C6 123.2(3) . . ?
C6 C5 C4 119.4(3) . . ?
H6A O6 H6B 104.5 . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3A 120.3 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.3(4) . . ?
C6 C7 H7 119.8 . . ?
O3 C4 C5 118.8(3) . . ?
C3 C4 O3 120.2(3) . . ?
C3 C4 C5 121.0(3) . . ?
O5 C6 C5 116.9(3) . . ?
O5 C6 C7 123.1(3) . . ?
C7 C6 C5 120.0(3) . . ?
O2 C1 C2 113.8(3) . . ?
O1 C1 O2 122.4(4) . . ?
O1 C1 C2 123.8(3) . . ?
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 H4 0.8200 . ?
O4 C5 1.376(4) . ?
O3 H3 0.8200 . ?
O3 C4 1.375(4) . ?
O5 H5 0.8200 . ?
O5 C6 1.376(4) . ?
O2 H2 0.8200 . ?
O2 C1 1.322(4) . ?
C2 C3 1.398(5) . ?
C2 C7 1.396(5) . ?
C2 C1 1.483(5) . ?
C5 C4 1.396(5) . ?
C5 C6 1.392(5) . ?
O6 H6A 0.8499 . ?
O6 H6B 0.8500 . ?
C3 H3A 0.9300 . ?
C3 C4 1.375(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.379(5) . ?
O1 C1 1.208(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C5 C4 O3 0.3(5) . . . . ?
O4 C5 C4 C3 -177.4(3) . . . . ?
O4 C5 C6 O5 -0.1(5) . . . . ?
O4 C5 C6 C7 179.2(3) . . . . ?
C2 C3 C4 O3 -179.0(3) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C2 C7 C6 O5 177.0(3) . . . . ?
C2 C7 C6 C5 -2.3(5) . . . . ?
C3 C2 C7 C6 2.6(6) . . . . ?
C3 C2 C1 O2 1.9(5) . . . . ?
C3 C2 C1 O1 -175.7(4) . . . . ?
C7 C2 C3 C4 -0.8(5) . . . . ?
C7 C2 C1 O2 178.8(4) . . . . ?
C7 C2 C1 O1 1.1(6) . . . . ?
C4 C5 C6 O5 -179.1(3) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C6 C5 C4 O3 179.3(3) . . . . ?
C6 C5 C4 C3 1.7(5) . . . . ?
C1 C2 C3 C4 176.1(3) . . . . ?
C1 C2 C7 C6 -174.4(3) . . . . ?
