#------------------------------------------------------------------------------
#$Date: 2016-05-06 03:45:51 +0300 (Fri, 06 May 2016) $
#$Revision: 182636 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/42/7224231.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_7224231
loop_
_publ_author_name
'Kaur, Ramanpreet'
'Cherukuvada, Suryanarayan'
'Managutti, Praveen B.'
'Row, Tayur N. Guru'
_publ_section_title
;
 A gallic acid--succinimide co-crystal landscape: polymorphism,
 pseudopolymorphism, variable stoichiometry co-crystals and concomitant
 growth of non-solvated and solvated co-crystals
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              3191
_journal_paper_doi               10.1039/C5CE01965F
_journal_volume                  18
_journal_year                    2016
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C7 H6 O5, C4 H5 N O2, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C13 H15 N O8'
_chemical_formula_weight         313.26
_chemical_name_systematic        '111 GASM 14D sovate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/cc1jg549
_audit_update_record
;
2016-01-21 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                109.507(5)
_cell_angle_beta                 95.486(4)
_cell_angle_gamma                101.807(4)
_cell_formula_units_Z            2
_cell_length_a                   4.9477(2)
_cell_length_b                   10.5762(5)
_cell_length_c                   13.8911(7)
_cell_measurement_reflns_used    6148
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      30.2944
_cell_measurement_theta_min      3.0565
_cell_volume                     660.00(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_publication_material  'PLATON (Spek, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8239
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.063
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0340
_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)+(0.0404P)²+0.2442P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0862
_reflns_number_gt                2282
_reflns_number_total             2581
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ce01965f1.cif
_cod_data_source_block           new
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7224231--7224237.cif.
;
_cod_database_code               7224231
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -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
C1 C 0.3338(3) 0.54722(13) 0.10067(10) 0.0144(3) Uani 1 1 d . .
C2 C 0.5870(3) 0.59351(13) 0.18213(9) 0.0147(3) Uani 1 1 d . .
C3 C 0.7989(3) 0.70397(13) 0.18494(10) 0.0151(3) Uani 1 1 d . .
H3 H 0.7809 0.7453 0.1343 0.018 Uiso 1 1 calc R U
C4 C 1.0367(3) 0.75413(13) 0.26136(10) 0.0144(3) Uani 1 1 d . .
C5 C 1.0612(3) 0.69205(14) 0.33472(10) 0.0150(3) Uani 1 1 d . .
C6 C 0.8489(3) 0.58094(14) 0.33150(10) 0.0158(3) Uani 1 1 d . .
C7 C 0.6104(3) 0.53058(13) 0.25533(10) 0.0155(3) Uani 1 1 d . .
H7 H 0.4655 0.4546 0.2530 0.019 Uiso 1 1 calc R U
C8 C 0.7211(3) 0.76292(14) 0.60643(10) 0.0174(3) Uani 1 1 d . .
C9 C 0.9089(3) 0.78438(15) 0.70524(10) 0.0202(3) Uani 1 1 d . .
H9A H 0.9789 0.7013 0.6993 0.024 Uiso 1 1 calc R U
H9B H 0.8079 0.8046 0.7646 0.024 Uiso 1 1 calc R U
C10 C 1.1502(3) 0.90850(15) 0.71883(11) 0.0206(3) Uani 1 1 d . .
H10A H 1.1483 0.9891 0.7807 0.025 Uiso 1 1 calc R U
H10B H 1.3331 0.8854 0.7267 0.025 Uiso 1 1 calc R U
C11 C 1.0998(3) 0.93918(14) 0.62156(10) 0.0169(3) Uani 1 1 d . .
C12 C 1.3101(3) 0.90583(15) 1.02616(12) 0.0253(3) Uani 1 1 d . .
H12A H 1.1483 0.8757 0.9689 0.030 Uiso 1 1 calc R U
H12B H 1.2638 0.8538 1.0724 0.030 Uiso 1 1 calc R U
C13 C 1.5654(3) 0.87354(16) 0.98226(12) 0.0256(3) Uani 1 1 d . .
H13A H 1.7237 0.8976 1.0398 0.031 Uiso 1 1 calc R U
H13B H 1.5259 0.7729 0.9419 0.031 Uiso 1 1 calc R U
N1 N 0.8452(2) 0.85331(12) 0.56284(9) 0.0180(3) Uani 1 1 d . .
O1 O 0.30501(19) 0.60716(10) 0.03971(7) 0.0173(2) Uani 1 1 d . .
O2 O 0.14326(19) 0.43885(10) 0.09937(7) 0.0190(2) Uani 1 1 d . .
O3 O 1.2393(2) 0.86531(10) 0.26519(7) 0.0188(2) Uani 1 1 d . .
O4 O 1.29617(19) 0.74577(10) 0.40928(7) 0.0187(2) Uani 1 1 d . .
O5 O 0.8986(2) 0.53043(11) 0.40849(8) 0.0223(2) Uani 1 1 d . .
O6 O 1.2501(2) 1.02522(10) 0.59684(7) 0.0216(2) Uani 1 1 d . .
O7 O 0.4912(2) 0.67983(11) 0.56966(8) 0.0246(2) Uani 1 1 d . .
O8 O 1.6424(2) 0.94915(10) 0.91683(7) 0.0224(2) Uani 1 1 d . .
H1N H 0.762(4) 0.861(2) 0.5048(15) 0.044(5) Uiso 1 1 d . .
H2O H -0.010(5) 0.424(2) 0.0485(16) 0.052(6) Uiso 1 1 d . .
H3O H 1.384(5) 0.882(2) 0.3127(16) 0.051(6) Uiso 1 1 d . .
H4O H 1.287(4) 0.694(2) 0.4463(16) 0.051(6) Uiso 1 1 d . .
H5O H 0.760(4) 0.467(2) 0.4078(15) 0.046(6) Uiso 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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
O1 C1 O2 123.02(12) . .
O1 C1 C2 121.75(12) . .
O2 C1 C2 115.23(11) . .
C3 C2 C7 120.78(12) . .
C3 C2 C1 117.78(12) . .
C7 C2 C1 121.42(12) . .
C4 C3 C2 120.19(12) . .
C4 C3 H3 119.9 . .
C2 C3 H3 119.9 . .
O3 C4 C3 119.63(11) . .
O3 C4 C5 121.00(11) . .
C3 C4 C5 119.34(12) . .
O4 C5 C6 122.20(12) . .
O4 C5 C4 117.44(12) . .
C6 C5 C4 120.36(12) . .
O5 C6 C7 125.12(12) . .
O5 C6 C5 114.37(11) . .
C7 C6 C5 120.51(12) . .
C6 C7 C2 118.82(12) . .
C6 C7 H7 120.6 . .
C2 C7 H7 120.6 . .
O7 C8 N1 124.28(12) . .
O7 C8 C9 126.64(12) . .
N1 C8 C9 109.07(11) . .
C8 C9 C10 104.42(11) . .
C8 C9 H9A 110.9 . .
C10 C9 H9A 110.9 . .
C8 C9 H9B 110.9 . .
C10 C9 H9B 110.9 . .
H9A C9 H9B 108.9 . .
C11 C10 C9 104.95(11) . .
C11 C10 H10A 110.8 . .
C9 C10 H10A 110.8 . .
C11 C10 H10B 110.8 . .
C9 C10 H10B 110.8 . .
H10A C10 H10B 108.8 . .
O6 C11 N1 124.33(12) . .
O6 C11 C10 127.30(12) . .
N1 C11 C10 108.36(11) . .
O8 C12 C13 110.95(12) 2_877 .
O8 C12 H12A 109.4 2_877 .
C13 C12 H12A 109.4 . .
O8 C12 H12B 109.4 2_877 .
C13 C12 H12B 109.4 . .
H12A C12 H12B 108.0 . .
O8 C13 C12 111.09(11) . .
O8 C13 H13A 109.4 . .
C12 C13 H13A 109.4 . .
O8 C13 H13B 109.4 . .
C12 C13 H13B 109.4 . .
H13A C13 H13B 108.0 . .
C8 N1 C11 112.83(11) . .
C8 N1 H1N 123.3(13) . .
C11 N1 H1N 123.7(13) . .
C1 O2 H2O 107.4(13) . .
C4 O3 H3O 111.0(14) . .
C5 O4 H4O 106.9(15) . .
C6 O5 H5O 112.3(14) . .
C13 O8 C12 109.59(11) . 2_877
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.2294(16) .
C1 O2 1.3205(16) .
C1 C2 1.4824(17) .
C2 C3 1.3876(18) .
C2 C7 1.3969(18) .
C3 C4 1.3866(18) .
C3 H3 0.9500 .
C4 O3 1.3625(16) .
C4 C5 1.3928(18) .
C5 O4 1.3615(15) .
C5 C6 1.3918(19) .
C6 O5 1.3690(16) .
C6 C7 1.3869(18) .
C7 H7 0.9500 .
C8 O7 1.2276(17) .
C8 N1 1.3694(17) .
C8 C9 1.5035(18) .
C9 C10 1.5277(19) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.5015(19) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 O6 1.2162(17) .
C11 N1 1.3848(17) .
C12 O8 1.4285(17) 2_877
C12 C13 1.506(2) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 O8 1.4276(17) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
N1 H1N 0.90(2) .
O2 H2O 0.93(2) .
O3 H3O 0.87(2) .
O4 H4O 0.86(2) .
O5 H5O 0.85(2) .
O8 C12 1.4284(17) 2_877
