#------------------------------------------------------------------------------
#$Date: 2024-01-06 10:05:41 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/74/7247478.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_7247478
loop_
_publ_author_name
'Ghouari, Nasreddine'
'Benali-Cherif, Rim'
'Takouachet, Radhwane'
'Falek, Wahiba'
'Missaoui, Djallila'
'Rahmouni, Ali'
'Bendeif, El-Eulmi'
'Benali-Cherif, Nourredine'
_publ_section_title
;
 Crystal engineering of a new pharmaceutical polymorph of gallic acid
 monohydrate: a structural comparative study and chemical computational
 quantum investigations
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              6279
_journal_page_last               6290
_journal_paper_doi               10.1039/D3CE00766A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C7 H8 O6'
_chemical_formula_weight         188.13
_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
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2023-09-07 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                100.593(3)
_cell_angle_beta                 91.274(3)
_cell_angle_gamma                111.564(3)
_cell_formula_units_Z            4
_cell_length_a                   7.1034(6)
_cell_length_b                   7.4941(6)
_cell_length_c                   15.5567(12)
_cell_measurement_reflns_used    51111
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.911
_cell_measurement_theta_min      2.677
_cell_volume                     753.39(11)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            51111
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.911
_diffrn_reflns_theta_min         2.677
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_description       Prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         8115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0505P)²+0.6060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1540
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6392
_reflns_number_total             8115
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00766a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7247478.cif.'
_cod_database_code               7247478
_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   0.925
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2014-1
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
O5A O -0.08063(13) 0.27213(11) 0.58029(5) 0.01033(14) Uani 1 1 d . . . . .
O6A O -0.15251(13) 0.47015(11) 0.73069(5) 0.01035(14) Uani 1 1 d . . . . .
O6B O 0.31603(14) 0.88207(12) 0.78559(6) 0.01327(15) Uani 1 1 d . . . . .
O1B O 0.24844(15) 0.43622(12) 1.00227(6) 0.01366(15) Uani 1 1 d . . . . .
C5A C -0.10980(15) 0.19359(14) 0.65318(6) 0.00713(15) Uani 1 1 d . . . . .
O2A O -0.16693(13) -0.23336(12) 0.87236(5) 0.01129(14) Uani 1 1 d . . . . .
O2B O 0.28621(14) 0.17104(12) 0.92486(5) 0.01173(14) Uani 1 1 d . . . . .
O4A O -0.05902(15) -0.08363(12) 0.57009(6) 0.01445(16) Uani 1 1 d . . . . .
C2B C 0.32256(15) 0.43925(14) 0.85561(6) 0.00783(15) Uani 1 1 d . . . . .
C2A C -0.16164(15) 0.02124(14) 0.79924(7) 0.00809(15) Uani 1 1 d . . . . .
O1A O -0.23298(15) 0.01958(13) 0.94614(6) 0.01480(16) Uani 1 1 d . . . . .
O5B O 0.39200(16) 0.68292(12) 0.63568(6) 0.01587(17) Uani 1 1 d . . . . .
C5B C 0.37104(17) 0.61095(14) 0.71026(7) 0.00960(16) Uani 1 1 d . . . . .
C6A C -0.14752(15) 0.29132(14) 0.73293(6) 0.00692(15) Uani 1 1 d . . . . .
O4B O 0.42523(15) 0.34566(13) 0.62521(6) 0.01619(17) Uani 1 1 d . . . . .
H4B H 0.3921 0.2276 0.6223 0.024 Uiso 1 1 calc R U . . .
C7A C -0.17677(16) 0.20475(14) 0.80571(7) 0.00823(15) Uani 1 1 d . . . . .
H7A H -0.2060 0.2674 0.8580 0.010 Uiso 1 1 calc R U . . .
C4A C -0.0963 0.0110 0.6481 0.009 Uani 1 1 d . . . . .
C6B C 0.33162(16) 0.70790(14) 0.78911(7) 0.00889(16) Uani 1 1 d . . . . .
C3B C 0.36573(16) 0.34365(14) 0.77735(7) 0.00856(16) Uani 1 1 d . . . . .
H3B H 0.3787 0.2235 0.7740 0.010 Uiso 1 1 calc R U . . .
C4B C 0.38908(16) 0.43003(14) 0.70473(7) 0.00891(16) Uani 1 1 d . . . . .
C7B C 0.30668(16) 0.62242(14) 0.86232(7) 0.00881(16) Uani 1 1 d . . . . .
H7B H 0.2798 0.6858 0.9150 0.011 Uiso 1 1 calc R U . . .
C1A C -0.18721(16) -0.07526(15) 0.87465(7) 0.00874(16) Uani 1 1 d . . . . .
C3A C -0.11959(16) -0.07431(15) 0.72069(7) 0.00913(16) Uani 1 1 d . . . . .
H3A H -0.1073 -0.1947 0.7172 0.011 Uiso 1 1 calc R U . . .
C1B C 0.28529(16) 0.33781(14) 0.92986(7) 0.00849(16) Uani 1 1 d . . . . .
O1W O 0.74998(13) 0.52330(12) 0.53923(6) 0.01176(14) Uani 1 1 d G . . . .
H1W H 0.6423 0.4872 0.5652 0.018 Uiso 1 1 d G U . . .
H2W H 0.7097 0.4768 0.4850 0.018 Uiso 1 1 d G U . . .
O2WA O 0.3629(3) 0.9865(2) 0.57832(12) 0.0146(5) Uani 0.541(7) 1 d G . P A 1
H1WA H 0.2391 0.9313 0.5572 0.022 Uiso 0.541(7) 1 d G U P A 1
H2WA H 0.4299 0.9879 0.5337 0.022 Uiso 0.541(7) 1 d G U P A 1
O2WB O 0.4049(3) 0.9733(2) 0.55990(12) 0.0142(6) Uani 0.459(7) 1 d G . P A 2
H2WB H 0.2962 0.9167 0.5254 0.021 Uiso 0.459(7) 1 d G U P A 2
H1WB H 0.3903 1.0725 0.5908 0.021 Uiso 0.459(7) 1 d G U P A 2
H5A H -0.1182 0.3632 0.5835 0.050 Uiso 1 1 d . U . . .
H6B H 0.2982 0.9404 0.8359 0.050 Uiso 1 1 d . U . . .
H6A H -0.1532 0.5324 0.7761 0.050 Uiso 1 1 d . U . . .
H1B H 0.2250 0.3634 1.0402 0.050 Uiso 1 1 d . U . . .
H1A H -0.2493 -0.0410 0.9861 0.050 Uiso 1 1 d . U . . .
H4A H -0.1122 -0.1972 0.5501 0.050 Uiso 1 1 d . U . . .
H5B H 0.3834 0.7882 0.6394 0.050 Uiso 1 1 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 '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
C5A O5A H5A 113.00 . . ?
C6A O6A H6A 115.00 . . ?
C6B O6B H6B 112.00 . . ?
C1B O1B H1B 108.00 . . ?
O5A C5A C4A 117.90(8) . . ?
O5A C5A C6A 122.47(9) . . ?
C4A C5A C6A 119.61(8) . . ?
C4A O4A H4A 125.00 . . ?
C3B C2B C7B 121.13(9) . . ?
C3B C2B C1B 117.83(9) . . ?
C7B C2B C1B 120.98(9) . . ?
C3A C2A C7A 120.71(9) . . ?
C3A C2A C1A 117.91(9) . . ?
C7A C2A C1A 121.38(9) . . ?
C1A O1A H1A 112.00 . . ?
C5B O5B H5B 116.00 . . ?
O5B C5B C4B 116.39(10) . . ?
O5B C5B C6B 123.16(9) . . ?
C4B C5B C6B 120.44(9) . . ?
O6A C6A C7A 125.25(9) . . ?
O6A C6A C5A 114.39(8) . . ?
C7A C6A C5A 120.35(9) . . ?
C4B O4B H4B 109.5 . . ?
C6A C7A C2A 119.09(9) . . ?
C6A C7A H7A 120.5 . . ?
C2A C7A H7A 120.5 . . ?
O4A C4A C3A 120.04(6) . . ?
O4A C4A C5A 119.38(5) . . ?
C3A C4A C5A 120.58(6) . . ?
O6B C6B C7B 125.45(10) . . ?
O6B C6B C5B 114.64(9) . . ?
C7B C6B C5B 119.89(9) . . ?
C4B C3B C2B 119.13(9) . . ?
C4B C3B H3B 120.4 . . ?
C2B C3B H3B 120.4 . . ?
O4B C4B C3B 123.39(9) . . ?
O4B C4B C5B 116.32(9) . . ?
C3B C4B C5B 120.27(10) . . ?
C6B C7B C2B 119.12(10) . . ?
C6B C7B H7B 120.4 . . ?
C2B C7B H7B 120.4 . . ?
O2A C1A O1A 121.90(9) . . ?
O2A C1A C2A 123.14(10) . . ?
O1A C1A C2A 114.96(9) . . ?
C4A C3A C2A 119.62(8) . . ?
C4A C3A H3A 120.2 . . ?
C2A C3A H3A 120.2 . . ?
O2B C1B O1B 121.98(9) . . ?
O2B C1B C2B 122.90(9) . . ?
O1B C1B C2B 115.11(9) . . ?
H1W O1W H2W 104.5 . . ?
H1WA O2WA H2WA 104.5 . . ?
H2WB O2WB H1WB 104.5 . . ?
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
O5A C5A 1.3570(12) . ?
O5A H5A 0.8100 . ?
O6A C6A 1.3603(12) . ?
O6A H6A 0.7700 . ?
O6B C6B 1.3606(13) . ?
O6B H6B 0.86000 . ?
O1B C1B 1.3157(13) . ?
O1B H1B 0.8500 . ?
C5A C4A 1.3947(10) . ?
C5A C6A 1.4044(14) . ?
O2A C1A 1.2394(13) . ?
O2B C1B 1.2403(13) . ?
O4A C4A 1.3711(8) . ?
O4A H4A 0.7900 . ?
C2B C3B 1.3954(15) . ?
C2B C7B 1.4034(14) . ?
C2B C1B 1.4734(14) . ?
C2A C3A 1.3954(15) . ?
C2A C7A 1.4040(14) . ?
C2A C1A 1.4686(14) . ?
O1A C1A 1.3203(14) . ?
O1A H1A 0.8200 . ?
O5B C5B 1.3556(13) . ?
O5B H5B 0.8100 . ?
C5B C4B 1.3955(15) . ?
C5B C6B 1.3958(15) . ?
C6A C7A 1.3883(14) . ?
O4B C4B 1.3573(13) . ?
O4B H4B 0.8200 . ?
C7A H7A 0.9300 . ?
C4A C3A 1.3816(10) . ?
C6B C7B 1.3902(14) . ?
C3B C4B 1.3859(14) . ?
C3B H3B 0.9300 . ?
C7B H7B 0.9300 . ?
C3A H3A 0.9300 . ?
O1W H1W 0.8501 . ?
O1W H2W 0.8501 . ?
O2WA H1WA 0.8500 . ?
O2WA H2WA 0.8501 . ?
O2WB H2WB 0.8499 . ?
O2WB H1WB 0.8498 . ?
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
O4B H4B O2WA 0.82 1.74 2.522(11) 157.9 1_545
O4B H4B O2WB 0.82 2.01 2.737(12) 147.9 1_545
C3B H3B O6B 0.93 2.47 3.3725(13) 162.7 1_545
C3A H3A O6A 0.93 2.46 3.3680(13) 164.9 1_545
O1W H1W O4B 0.85 1.90 2.7234(12) 163.4 .
O1W H2W O5B 0.85 1.99 2.8278(12) 168.6 2_666
O2WA H1WA O5A 0.85 2.37 3.005(2) 132.4 2_566
O2WA H1WA O4A 0.85 2.10 2.8417(19) 146.3 1_565
O2WB H2WB O5A 0.85 2.12 2.938(2) 161.9 2_566
O2WB H2WB O4A 0.85 2.63 3.1754(19) 123.0 1_565
O2WB H1WB O4B 0.85 1.94 2.7375(15) 156.2 1_565
O5A H5A O1W 0.8100 1.97 2.7334(11) 155.44(6) 1_455
O6B H6B O2B 0.8600 2.0400 2.8392(12) 155.24(6) 1_565
O6A H6A O2A 0.7700 2.1200 2.8604(12) 160.19(6) 1_565
O1B H1B O2A 0.8500 1.7900 2.6350(11) 172.93(6) 2_557
O1A H1A O2B 0.8200 1.8100 2.6271(12) 179.04(7) 2_557
O4A H4A O1W 0.7900 1.93 2.6947(12) 162.22(7) 1_445
O5B H5B O2WA 0.8100 1.9508(12) 2.6647(13) 147.39(8) .
O5B H5B O2WB 0.8100 1.9904(13) 2.6338(13) 136.55(8) .
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
O5A C5A C6A O6A 0.09(14) . . . . ?
C4A C5A C6A O6A 178.47(8) . . . . ?
O5A C5A C6A C7A 179.88(9) . . . . ?
C4A C5A C6A C7A -1.74(14) . . . . ?
O6A C6A C7A C2A -178.20(10) . . . . ?
C5A C6A C7A C2A 2.03(15) . . . . ?
C3A C2A C7A C6A -0.57(16) . . . . ?
C1A C2A C7A C6A 178.79(9) . . . . ?
O5A C5A C4A O4A -1.41(11) . . . . ?
C6A C5A C4A O4A -179.86(8) . . . . ?
O5A C5A C4A C3A 178.40(8) . . . . ?
C6A C5A C4A C3A -0.05(12) . . . . ?
O5B C5B C6B O6B -0.13(16) . . . . ?
C4B C5B C6B O6B -179.52(10) . . . . ?
O5B C5B C6B C7B 178.29(10) . . . . ?
C4B C5B C6B C7B -1.09(16) . . . . ?
C7B C2B C3B C4B -1.32(16) . . . . ?
C1B C2B C3B C4B 176.06(9) . . . . ?
C2B C3B C4B O4B -177.99(10) . . . . ?
C2B C3B C4B C5B 0.48(16) . . . . ?
O5B C5B C4B O4B -0.13(15) . . . . ?
C6B C5B C4B O4B 179.29(10) . . . . ?
O5B C5B C4B C3B -178.70(10) . . . . ?
C6B C5B C4B C3B 0.72(16) . . . . ?
O6B C6B C7B C2B 178.50(10) . . . . ?
C5B C6B C7B C2B 0.26(15) . . . . ?
C3B C2B C7B C6B 0.95(16) . . . . ?
C1B C2B C7B C6B -176.35(9) . . . . ?
C3A C2A C1A O2A 2.33(16) . . . . ?
C7A C2A C1A O2A -177.05(10) . . . . ?
C3A C2A C1A O1A -177.97(10) . . . . ?
C7A C2A C1A O1A 2.65(15) . . . . ?
O4A C4A C3A C2A -178.69(9) . . . . ?
C5A C4A C3A C2A 1.50(12) . . . . ?
C7A C2A C3A C4A -1.20(15) . . . . ?
C1A C2A C3A C4A 179.42(8) . . . . ?
C3B C2B C1B O2B -1.69(16) . . . . ?
C7B C2B C1B O2B 175.70(10) . . . . ?
C3B C2B C1B O1B 179.01(10) . . . . ?
C7B C2B C1B O1B -3.60(15) . . . . ?
