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#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/75/7207534.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_7207534
loop_
_publ_author_name
'Moragues-Bartolome, Alaina M.'
'Jones, William'
'Cruz-Cabeza, Aurora J.'
_publ_section_title
;
 Synthon preferences in cocrystals of cis-carboxamides:carboxylic acids
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2552
_journal_paper_doi               10.1039/c2ce06241k
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C7 H4 N2 O6, C4 H7 N O'
_chemical_formula_sum            'C11 H11 N3 O7'
_chemical_formula_weight         297.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.489(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4528(5)
_cell_length_b                   6.3801(3)
_cell_length_c                   17.643(1)
_cell_measurement_reflns_used    13810
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      20.82
_cell_measurement_theta_min      1.02
_cell_volume                     1289.13(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7418
_diffrn_reflns_theta_full        20.77
_diffrn_reflns_theta_max         20.77
_diffrn_reflns_theta_min         3.56
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         1330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0535P)²+0.3401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                1094
_reflns_number_total             1330
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce06241k.txt
_cod_data_source_block           1k
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7207534
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.56371(16) -0.5994(3) 0.10387(13) 0.0393(6) Uani 1 1 d .
H1 H 0.5592(19) -0.681(4) 0.0516(14) 0.047 Uiso 1 1 d .
C2 C 0.6076(2) -0.6875(4) 0.17476(15) 0.0495(8) Uani 1 1 d .
H2A H 0.6834 -0.7591 0.1673 0.059 Uiso 1 1 calc R
H2B H 0.5513 -0.7882 0.1964 0.059 Uiso 1 1 calc R
C3 C 0.6217(2) -0.4951(4) 0.22570(16) 0.0514(7) Uani 1 1 d .
H3A H 0.7022 -0.4389 0.2234 0.062 Uiso 1 1 calc R
H3B H 0.6030 -0.5290 0.2790 0.062 Uiso 1 1 calc R
C4 C 0.5337(2) -0.3398(4) 0.19219(15) 0.0498(7) Uani 1 1 d .
H4A H 0.4587 -0.3457 0.2196 0.060 Uiso 1 1 calc R
H4B H 0.5643 -0.1948 0.1943 0.060 Uiso 1 1 calc R
C5 C 0.5190(2) -0.4111(4) 0.11270(15) 0.0366(6) Uani 1 1 d .
O6 O 0.47020(16) -0.3112(3) 0.05995(11) 0.0549(6) Uani 1 1 d .
C7 C 0.1969(2) 0.3874(4) -0.03133(15) 0.0393(7) Uani 1 1 d .
H7 H 0.2020 0.3228 -0.0797 0.047 Uiso 1 1 calc R
C8 C 0.24734(19) 0.2939(3) 0.03166(15) 0.0349(6) Uani 1 1 d .
C9 C 0.2369(2) 0.3864(3) 0.10214(14) 0.0380(7) Uani 1 1 d .
H9 H 0.2704 0.3229 0.1459 0.046 Uiso 1 1 calc R
C10 C 0.1761(2) 0.5745(4) 0.10755(15) 0.0392(7) Uani 1 1 d .
C11 C 0.1276(2) 0.6728(4) 0.04583(16) 0.0422(7) Uani 1 1 d .
H11 H 0.0877 0.8026 0.0505 0.051 Uiso 1 1 calc R
C12 C 0.1391(2) 0.5755(4) -0.02303(15) 0.0391(7) Uani 1 1 d .
C13 C 0.3114(2) 0.0910(4) 0.02156(17) 0.0392(7) Uani 1 1 d .
O14 O 0.36661(16) 0.0316(3) 0.08265(11) 0.0514(6) Uani 1 1 d .
H14 H 0.402(2) -0.082(4) 0.0770(15) 0.062 Uiso 1 1 d .
O15 O 0.30983(15) -0.0026(3) -0.03840(11) 0.0521(5) Uani 1 1 d .
N16 N 0.1614(2) 0.6716(4) 0.18251(15) 0.0554(7) Uani 1 1 d .
O17 O 0.2062(2) 0.5887(3) 0.23685(13) 0.0862(8) Uani 1 1 d .
O18 O 0.10359(19) 0.8301(3) 0.18656(12) 0.0808(7) Uani 1 1 d .
N19 N 0.08491(19) 0.6746(4) -0.09051(16) 0.0548(7) Uani 1 1 d .
O20 O 0.03448(18) 0.8412(3) -0.08199(12) 0.0740(7) Uani 1 1 d .
O21 O 0.09190(18) 0.5823(4) -0.15107(13) 0.0724(7) Uani 1 1 d .
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
C5 N1 C2 112.5(2)
C5 N1 H1 122.4(13)
C2 N1 H1 124.8(13)
N1 C2 C3 103.2(2)
N1 C2 H2A 111.1
C3 C2 H2A 111.1
N1 C2 H2B 111.1
C3 C2 H2B 111.1
H2A C2 H2B 109.1
C2 C3 C4 103.1(2)
C2 C3 H3A 111.1
C4 C3 H3A 111.1
C2 C3 H3B 111.1
C4 C3 H3B 111.1
H3A C3 H3B 109.1
C5 C4 C3 103.7(2)
C5 C4 H4A 111.0
C3 C4 H4A 111.0
C5 C4 H4B 111.0
C3 C4 H4B 111.0
H4A C4 H4B 109.0
O6 C5 N1 123.2(2)
O6 C5 C4 126.3(2)
N1 C5 C4 110.5(2)
C12 C7 C8 119.2(2)
C12 C7 H7 120.4
C8 C7 H7 120.4
C9 C8 C7 120.0(2)
C9 C8 C13 121.5(2)
C7 C8 C13 118.6(2)
C8 C9 C10 118.5(2)
C8 C9 H9 120.7
C10 C9 H9 120.7
C11 C10 C9 122.7(2)
C11 C10 N16 118.2(2)
C9 C10 N16 119.1(2)
C10 C11 C12 117.1(2)
C10 C11 H11 121.4
C12 C11 H11 121.4
C11 C12 C7 122.5(2)
C11 C12 N19 118.5(2)
C7 C12 N19 119.0(3)
O15 C13 O14 125.5(2)
O15 C13 C8 121.6(3)
O14 C13 C8 112.8(2)
C13 O14 H14 112.6(19)
O17 N16 O18 123.3(2)
O17 N16 C10 118.6(2)
O18 N16 C10 118.1(3)
O20 N19 O21 124.2(2)
O20 N19 C12 118.0(3)
O21 N19 C12 117.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.316(3)
N1 C2 1.457(3)
N1 H1 1.06(2)
C2 C3 1.529(4)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.529(4)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.482(4)
C4 H4A 0.9900
C4 H4B 0.9900
C5 O6 1.255(3)
C7 C12 1.379(3)
C7 C8 1.383(3)
C7 H7 0.9500
C8 C9 1.383(3)
C8 C13 1.499(3)
C9 C10 1.391(3)
C9 H9 0.9500
C10 C11 1.370(3)
C10 N16 1.471(3)
C11 C12 1.371(3)
C11 H11 0.9500
C12 N19 1.480(3)
C13 O15 1.215(3)
C13 O14 1.301(3)
O14 H14 0.84(3)
N16 O17 1.206(3)
N16 O18 1.211(3)
N19 O20 1.220(3)
N19 O21 1.223(3)
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
C5 N1 C2 C3 -18.9(3)
N1 C2 C3 C4 25.5(3)
C2 C3 C4 C5 -23.7(3)
C2 N1 C5 O6 -175.8(2)
C2 N1 C5 C4 3.5(3)
C3 C4 C5 O6 -167.2(2)
C3 C4 C5 N1 13.5(3)
C12 C7 C8 C9 1.6(3)
C12 C7 C8 C13 -179.13(19)
C7 C8 C9 C10 -0.7(3)
C13 C8 C9 C10 -179.9(2)
C8 C9 C10 C11 -0.8(3)
C8 C9 C10 N16 178.2(2)
C9 C10 C11 C12 1.3(3)
N16 C10 C11 C12 -177.78(19)
C10 C11 C12 C7 -0.3(3)
C10 C11 C12 N19 178.4(2)
C8 C7 C12 C11 -1.2(3)
C8 C7 C12 N19 -179.8(2)
C9 C8 C13 O15 171.7(2)
C7 C8 C13 O15 -7.6(3)
C9 C8 C13 O14 -8.5(3)
C7 C8 C13 O14 172.2(2)
C11 C10 N16 O17 -178.2(2)
C9 C10 N16 O17 2.7(4)
C11 C10 N16 O18 2.5(3)
C9 C10 N16 O18 -176.6(2)
C11 C12 N19 O20 1.5(3)
C7 C12 N19 O20 -179.8(2)
C11 C12 N19 O21 -177.2(2)
C7 C12 N19 O21 1.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139196262
