#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/67/1556770.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_1556770
loop_
_publ_author_name
'Kaur, Ramanpreet'
'Gautam, Raj'
'Cherukuvada, Suryanarayan'
'Guru Row, Tayur N.'
_publ_section_title
;
 Do carboximide-carboxylic acid combinations form co-crystals? The role of
 hydroxyl substitution on the formation of co-crystals and eutectics.
;
_journal_issue                   'Pt 3'
_journal_name_full               IUCrJ
_journal_page_first              341
_journal_page_last               351
_journal_paper_doi               10.1107/S2052252515002651
_journal_volume                  2
_journal_year                    2015
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C7 H6 O4, C5 H7 N O2'
_chemical_formula_sum            'C12 H13 N O6'
_chemical_formula_weight         267.23
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_cell_angle_alpha                93.397(3)
_cell_angle_beta                 107.694(3)
_cell_angle_gamma                108.173(4)
_cell_formula_units_Z            2
_cell_length_a                   6.6761(3)
_cell_length_b                   9.1128(4)
_cell_length_c                   10.9447(4)
_cell_measurement_reflns_used    8252
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.1140
_cell_measurement_theta_min      3.2940
_cell_volume                     593.92(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_publication_material  'PLATON (Spek, 2003)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'four-circle diffractometer'
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11839
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.387
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0312
_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)+(0.0468P)²+0.1835P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0884
_reflns_number_gt                2156
_reflns_number_total             2329
_publcif_datablock.id            {4224c4ed-45de-4d72-9e9f-90afae20d70e}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_data_source_file            bi5039.cif
_cod_data_source_block           GM-35DHBA
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/IUCr/depositions/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 
;
_cod_database_code               1556770
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 0.45954(18) 1.19843(13) 0.70572(10) 0.0142(2) Uani 1 1 d . .
C2 C 0.24590(18) 1.07724(13) 0.70006(10) 0.0135(2) Uani 1 1 d . .
C3 C 0.15543(19) 0.93734(13) 0.61184(10) 0.0138(2) Uani 1 1 d . .
H3 H 0.2313 0.9158 0.5561 0.017 Uiso 1 1 calc R U
C4 C -0.04910(18) 0.82974(13) 0.60721(10) 0.0140(2) Uani 1 1 d . .
C5 C -0.15994(18) 0.86142(13) 0.68862(11) 0.0150(2) Uani 1 1 d . .
H5 H -0.3000 0.7877 0.6838 0.018 Uiso 1 1 calc R U
C6 C -0.06628(19) 1.00086(13) 0.77722(11) 0.0144(2) Uani 1 1 d . .
C7 C 0.13857(19) 1.10988(13) 0.78395(11) 0.0145(2) Uani 1 1 d . .
H7 H 0.2040 1.2049 0.8447 0.017 Uiso 1 1 calc R U
C8 C -0.05943(19) 0.50595(13) 0.27529(11) 0.0143(2) Uani 1 1 d . .
C9 C -0.29426(19) 0.40960(14) 0.26388(12) 0.0162(3) Uani 1 1 d . .
C10 C -0.43280(19) 0.32214(14) 0.12572(11) 0.0170(3) Uani 1 1 d . .
C11 C -0.30912(19) 0.22792(13) 0.07950(11) 0.0153(2) Uani 1 1 d . .
C12 C -0.07691(18) 0.32979(13) 0.09069(11) 0.0139(2) Uani 1 1 d . .
N1 N 0.02769(16) 0.46033(11) 0.18822(9) 0.0148(2) Uani 1 1 d . .
O1 O 0.54761(13) 1.32048(9) 0.78454(8) 0.0175(2) Uani 1 1 d . .
O2 O 0.54367(14) 1.16248(10) 0.61820(8) 0.0182(2) Uani 1 1 d . .
O3 O -0.15073(14) 0.69014(9) 0.52418(8) 0.0179(2) Uani 1 1 d . .
O4 O -0.18242(14) 1.02460(10) 0.85444(8) 0.0194(2) Uani 1 1 d . .
O5 O 0.05505(13) 0.62391(9) 0.35880(8) 0.0175(2) Uani 1 1 d . .
O6 O 0.02443(14) 0.30476(10) 0.02066(8) 0.0184(2) Uani 1 1 d . .
H1N H 0.170(3) 0.5229(19) 0.1952(15) 0.028(4) Uiso 1 1 d . .
H2O H 0.670(3) 1.235(2) 0.6290(16) 0.030(4) Uiso 1 1 d . .
H3O H -0.078(3) 0.6801(19) 0.4761(17) 0.033(4) Uiso 1 1 d . .
H4O H -0.113(3) 1.114(2) 0.9064(17) 0.036(4) Uiso 1 1 d . .
H9A H -0.281(2) 0.3348(16) 0.3251(13) 0.017(3) Uiso 1 1 d . .
H9B H -0.357(2) 0.4804(18) 0.2971(14) 0.026(4) Uiso 1 1 d . .
H10A H -0.578(2) 0.2551(17) 0.1233(13) 0.020(3) Uiso 1 1 d . .
H10B H -0.453(2) 0.3969(18) 0.0689(14) 0.024(4) Uiso 1 1 d . .
H11A H -0.292(2) 0.1484(16) 0.1349(13) 0.017(3) Uiso 1 1 d . .
H11B H -0.388(2) 0.1740(16) -0.0110(14) 0.019(3) 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
O1 C1 O2 123.47(10)
O1 C1 C2 122.48(10)
O2 C1 C2 114.05(9)
C3 C2 C7 121.56(10)
C3 C2 C1 120.63(10)
C7 C2 C1 117.80(10)
C2 C3 C4 118.46(10)
O3 C4 C5 116.55(10)
O3 C4 C3 122.71(10)
C5 C4 C3 120.73(10)
C4 C5 C6 120.14(10)
O4 C6 C5 117.31(10)
O4 C6 C7 122.58(10)
C5 C6 C7 120.11(10)
C6 C7 C2 118.98(10)
O5 C8 N1 119.41(10)
O5 C8 C9 122.74(10)
N1 C8 C9 117.85(10)
C8 C9 C10 111.95(9)
C11 C10 C9 109.62(10)
C12 C11 C10 111.52(9)
O6 C12 N1 118.51(10)
O6 C12 C11 124.51(10)
N1 C12 C11 116.98(9)
C8 N1 C12 126.49(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2235(13)
C1 O2 1.3210(13)
C1 C2 1.4877(15)
C2 C3 1.3934(16)
C2 C7 1.3948(16)
C3 C4 1.3948(16)
C4 O3 1.3618(13)
C4 C5 1.3886(16)
C5 C6 1.3913(16)
C6 O4 1.3578(14)
C6 C7 1.3947(16)
C8 O5 1.2335(14)
C8 N1 1.3638(15)
C8 C9 1.5013(15)
C9 C10 1.5246(16)
C10 C11 1.5230(16)
C11 C12 1.5012(15)
C12 O6 1.2198(14)
C12 N1 1.3858(14)
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
O1 C1 C2 C3 -177.67(11)
O2 C1 C2 C3 2.59(15)
O1 C1 C2 C7 3.47(17)
O2 C1 C2 C7 -176.27(10)
C7 C2 C3 C4 0.99(17)
C1 C2 C3 C4 -177.83(10)
C2 C3 C4 O3 179.90(10)
C2 C3 C4 C5 0.03(17)
O3 C4 C5 C6 179.38(10)
C3 C4 C5 C6 -0.75(18)
C4 C5 C6 O4 -179.73(10)
C4 C5 C6 C7 0.46(17)
O4 C6 C7 C2 -179.27(10)
C5 C6 C7 C2 0.53(17)
C3 C2 C7 C6 -1.27(17)
C1 C2 C7 C6 177.58(10)
O5 C8 C9 C10 153.92(11)
N1 C8 C9 C10 -25.49(15)
C8 C9 C10 C11 53.06(13)
C9 C10 C11 C12 -54.94(13)
C10 C11 C12 O6 -151.08(11)
C10 C11 C12 N1 29.28(14)
O5 C8 N1 C12 178.68(10)
C9 C8 N1 C12 -1.89(17)
O6 C12 N1 C8 -179.77(10)
C11 C12 N1 C8 -0.11(17)
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{3f1a2864-dc54-4856-91f5-e0ca14c59c2b} ? ? ?
{fc914b0b-407d-4e47-8dd1-1ad18a2e50e1} y y y
{7f25c736-1ee1-4b65-ba1d-0ff73615c4eb} y y y
{5ede9a71-6d16-4c08-8ac7-a5bb0d091103} y y y
{d0b81d9a-6811-4b6f-9200-1893691e7239} y y y
{3d020128-fe82-4a7d-8b68-ced197e40c3e} y y y
{b7188455-bc7c-4376-bda0-510706e5a275} y y y
{b4f189a4-1a18-4453-b7d1-1d82974a8e0e} y y y
{f7cb94d9-d865-4652-a567-86f93c0dae79} y y y
{67cd5b8f-dccc-4742-b995-b296c5b02f90} y y y
{f40093aa-b9f2-4ba0-8222-27709be5f309} y y y
{4224c4ed-45de-4d72-9e9f-90afae20d70e} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305933
