#------------------------------------------------------------------------------
#$Date: 2024-09-06 03:16:30 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294519 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/90/7249074.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_7249074
loop_
_publ_author_name
'Yang, Mingzhu'
'Jiang, Zhouyu'
'Du, Cunbin'
'Zhang, Xiaowen'
'Wang, Mingliang'
_publ_section_title
;
 Chemical stabilization strategy for cymoxanil: synthesis and
 characterization of cocrystals with small organic acids
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              4214
_journal_page_last               4222
_journal_paper_doi               10.1039/D4CE00513A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C7 H10 N4 O3, C7 H6 O3'
_chemical_formula_sum            'C14 H16 N4 O6'
_chemical_formula_weight         336.31
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2024-06-26 deposited with the CCDC.	2024-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                86.267(2)
_cell_angle_beta                 81.573(2)
_cell_angle_gamma                83.375(2)
_cell_formula_units_Z            2
_cell_length_a                   4.9580(2)
_cell_length_b                   11.3093(6)
_cell_length_c                   14.6326(8)
_cell_measurement_reflns_used    2089
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      62.35
_cell_measurement_theta_min      3.06
_cell_volume                     805.22(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2803
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.580
_diffrn_reflns_theta_max         66.580
_diffrn_reflns_theta_min         3.057
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1188 before and 0.0594 after correction.
The Ratio of minimum to maximum transmission is 0.7794.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0703
_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)+(0.0993P)²+0.5907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2215
_refine_ls_wR_factor_ref         0.2291
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2140
_reflns_number_total             2803
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00513a2.cif
_cod_data_source_block           1_a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7249073--7249074.cif.'
_cod_database_code               7249074
_shelx_shelxl_version_number     2014/7
_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_max   0.849
_shelx_estimated_absorpt_t_min   0.820
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), N3(H3), N4(H4)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C7(H7A,H7B,H7C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
C1 C 0.6003(10) 0.9464(4) 0.6197(3) 0.0941(14) Uani 1 1 d . . . . .
H1A H 0.6175 1.0275 0.5980 0.141 Uiso 1 1 calc R U . . .
H1B H 0.6034 0.9391 0.6853 0.141 Uiso 1 1 calc R U . . .
H1C H 0.4302 0.9236 0.6063 0.141 Uiso 1 1 calc R U . . .
C2 C 1.2297(8) 0.7206(3) 0.5045(3) 0.0698(9) Uani 1 1 d . . . . .
C3 C 1.0148(7) 0.6837(3) 0.5745(2) 0.0619(8) Uani 1 1 d . . . . .
C4 C 1.0402(7) 0.5560(3) 0.6075(2) 0.0640(9) Uani 1 1 d . . . . .
C5 C 0.8280(7) 0.4067(3) 0.7161(3) 0.0612(8) Uani 1 1 d . . . . .
C6 C 1.0293(8) 0.2015(3) 0.7304(3) 0.0800(11) Uani 1 1 d . . . . .
H6A H 1.1372 0.1484 0.6862 0.096 Uiso 1 1 calc R U . . .
H6B H 0.8426 0.1805 0.7395 0.096 Uiso 1 1 calc R U . . .
C7 C 1.1403(10) 0.1826(4) 0.8196(4) 0.0985(15) Uani 1 1 d . . . . .
H7A H 1.3258 0.2024 0.8112 0.148 Uiso 1 1 calc R U . . .
H7B H 1.1366 0.1007 0.8410 0.148 Uiso 1 1 calc R U . . .
H7C H 1.0303 0.2327 0.8646 0.148 Uiso 1 1 calc R U . . .
C8 C 1.1719(7) 0.6251(3) 0.8241(2) 0.0624(8) Uani 1 1 d . . . . .
C9 C 0.9325(7) 0.6966(3) 0.8709(2) 0.0626(8) Uani 1 1 d . . . . .
C10 C 0.7530(8) 0.6468(4) 0.9412(3) 0.0743(10) Uani 1 1 d . . . . .
H10 H 0.7850 0.5665 0.9588 0.089 Uiso 1 1 calc R U . . .
C11 C 0.5284(8) 0.7149(4) 0.9850(3) 0.0853(12) Uani 1 1 d . . . . .
H11 H 0.4090 0.6810 1.0318 0.102 Uiso 1 1 calc R U . . .
C12 C 0.4830(9) 0.8341(4) 0.9587(3) 0.0899(13) Uani 1 1 d . . . . .
H12 H 0.3308 0.8801 0.9877 0.108 Uiso 1 1 calc R U . . .
C13 C 0.6578(9) 0.8861(4) 0.8905(3) 0.0842(12) Uani 1 1 d . . . . .
H13 H 0.6250 0.9667 0.8742 0.101 Uiso 1 1 calc R U . . .
C14 C 0.8849(8) 0.8179(3) 0.8456(3) 0.0694(9) Uani 1 1 d . . . . .
N1 N 0.8132(6) 0.7557(2) 0.6103(2) 0.0678(8) Uani 1 1 d . . . . .
N2 N 1.3980(8) 0.7517(3) 0.4503(3) 0.0881(10) Uani 1 1 d . . . . .
N3 N 0.8414(5) 0.5222(2) 0.67404(19) 0.0606(7) Uani 1 1 d . . . . .
H3 H 0.7112 0.5760 0.6925 0.073 Uiso 1 1 calc R U . . .
N4 N 1.0304(6) 0.3239(2) 0.6918(2) 0.0693(8) Uani 1 1 d . . . . .
H4 H 1.1669 0.3423 0.6522 0.083 Uiso 1 1 calc R U . . .
O1 O 0.8248(6) 0.8698(2) 0.57405(19) 0.0799(8) Uani 1 1 d . . . . .
O2 O 1.2363(6) 0.4918(2) 0.5730(2) 0.0927(10) Uani 1 1 d . . . . .
O3 O 0.6261(5) 0.3890(2) 0.7730(2) 0.0793(8) Uani 1 1 d . . . . .
O4 O 1.2039(5) 0.5129(2) 0.85395(19) 0.0763(8) Uani 1 1 d . . . . .
H4A H 1.3404 0.4788 0.8242 0.114 Uiso 1 1 calc R U . . .
O5 O 1.3306(5) 0.6656(2) 0.75958(18) 0.0736(7) Uani 1 1 d . . . . .
O6 O 1.0519(6) 0.8729(2) 0.7788(2) 0.0870(8) Uani 1 1 d . . . . .
H6 H 1.1843 0.8259 0.7603 0.131 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
N2 C2 C3 178.6(4) . . ?
C2 C3 C4 116.7(3) . . ?
N1 C3 C2 123.3(3) . . ?
N1 C3 C4 119.9(3) . . ?
N3 C4 C3 116.6(3) . . ?
O2 C4 C3 117.6(3) . . ?
O2 C4 N3 125.7(3) . . ?
N4 C5 N3 118.3(3) . . ?
O3 C5 N3 118.0(3) . . ?
O3 C5 N4 123.7(3) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
N4 C6 H6A 108.9 . . ?
N4 C6 H6B 108.9 . . ?
N4 C6 C7 113.4(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 C9 115.2(3) . . ?
O5 C8 C9 122.9(3) . . ?
O5 C8 O4 121.8(3) . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 C14 119.2(3) . . ?
C14 C9 C8 119.5(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.2(4) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.3(4) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 119.4(4) . . ?
O6 C14 C9 122.6(3) . . ?
O6 C14 C13 118.0(4) . . ?
C3 N1 O1 112.4(3) . . ?
C4 N3 C5 125.9(3) . . ?
C4 N3 H3 117.0 . . ?
C5 N3 H3 117.0 . . ?
C5 N4 C6 121.8(3) . . ?
C5 N4 H4 119.1 . . ?
C6 N4 H4 119.1 . . ?
N1 O1 C1 109.5(3) . . ?
C8 O4 H4A 109.5 . . ?
C14 O6 H6 109.5 . . ?
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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 O1 1.439(5) . ?
C2 C3 1.444(5) . ?
C2 N2 1.134(5) . ?
C3 C4 1.491(5) . ?
C3 N1 1.285(4) . ?
C4 N3 1.350(4) . ?
C4 O2 1.211(4) . ?
C5 N3 1.411(4) . ?
C5 N4 1.317(4) . ?
C5 O3 1.231(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.484(6) . ?
C6 N4 1.461(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.465(5) . ?
C8 O4 1.314(4) . ?
C8 O5 1.236(4) . ?
C9 C10 1.392(5) . ?
C9 C14 1.400(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.394(5) . ?
C14 O6 1.353(5) . ?
N1 O1 1.366(3) . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?
O4 H4A 0.8200 . ?
O6 H6 0.8200 . ?
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
C2 C3 C4 N3 178.9(3) . . . . ?
C2 C3 C4 O2 -0.7(5) . . . . ?
C2 C3 N1 O1 0.6(5) . . . . ?
C3 C4 N3 C5 -178.8(3) . . . . ?
C3 N1 O1 C1 -177.6(3) . . . . ?
C4 C3 N1 O1 178.4(3) . . . . ?
C7 C6 N4 C5 -85.7(5) . . . . ?
C8 C9 C10 C11 179.9(4) . . . . ?
C8 C9 C14 C13 -179.7(3) . . . . ?
C8 C9 C14 O6 0.1(5) . . . . ?
C9 C10 C11 C12 -0.2(6) . . . . ?
C10 C9 C14 C13 -0.5(5) . . . . ?
C10 C9 C14 O6 179.2(3) . . . . ?
C10 C11 C12 C13 -0.6(7) . . . . ?
C11 C12 C13 C14 0.8(7) . . . . ?
C12 C13 C14 C9 -0.2(6) . . . . ?
C12 C13 C14 O6 -179.9(4) . . . . ?
C14 C9 C10 C11 0.8(6) . . . . ?
N1 C3 C4 N3 1.0(5) . . . . ?
N1 C3 C4 O2 -178.6(4) . . . . ?
N3 C5 N4 C6 -178.6(3) . . . . ?
N4 C5 N3 C4 2.7(5) . . . . ?
O2 C4 N3 C5 0.7(6) . . . . ?
O3 C5 N3 C4 -176.8(3) . . . . ?
O3 C5 N4 C6 0.9(6) . . . . ?
O4 C8 C9 C10 -0.7(5) . . . . ?
O4 C8 C9 C14 178.4(3) . . . . ?
O5 C8 C9 C10 177.7(3) . . . . ?
O5 C8 C9 C14 -3.1(5) . . . . ?
