Cocrystal engineering strategy for sustained release and leaching reduction of herbicides: a case study of metamitron
Xiao, Yuntian; Wu, Chuanhua; Zhou, Ling; Yin, Qiuxiang; Yang, Jingxiang; Green Chemistry 24 (2022) 8088–8099; doi:10.1039/D2GC02949A

data_7245548
_publ_section_title
;
 Cocrystal engineering strategy for sustained release and leaching
 reduction of herbicides: a case study of metamitron
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              8088
_journal_page_last               8099
_journal_paper_doi               10.1039/D2GC02949A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C10 H10 N4 O, C15 H12 O5'
_chemical_formula_sum            'C25 H22 N4 O6'
_chemical_formula_weight         474.46
_chemical_name_systematic        Metamitron-Naringenin
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-12-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.16 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_audit_update_record
;
2022-05-07 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.770(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8352(12)
_cell_length_b                   14.4349(12)
_cell_length_c                   6.7368(8)
_cell_measurement_reflns_used    4761
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.6800
_cell_measurement_theta_min      2.2610
_cell_volume                     1107.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -115.00  65.00   1.00   25.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  65.00   1.00   25.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00   25.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0026418000
_diffrn_orient_matrix_UB_12      -0.0489391000
_diffrn_orient_matrix_UB_13      0.0094520000
_diffrn_orient_matrix_UB_21      -0.0618443000
_diffrn_orient_matrix_UB_22      -0.0024868000
_diffrn_orient_matrix_UB_23      -0.0403646000
_diffrn_orient_matrix_UB_31      0.0066708000
_diffrn_orient_matrix_UB_32      -0.0035781000
_diffrn_orient_matrix_UB_33      -0.1012611000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10628
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        24.984
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_min         2.278
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95779
_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_density_diffrn    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1028 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3759
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0574
_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/[\s^2^(Fo^2^)+(0.0594P)^2^+0.5791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1459
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                2848
_reflns_number_total             3759
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02949a2.cif
_cod_data_source_block           r20211203a
_cod_depositor_comments
'Adding full bibliography for 7245547--7245549.cif.'
_cod_original_sg_symbol_H-M      Pc
_cod_database_code               7245548
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.947(2)
 0.053(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Rotating group:
 N1(H1A,H1B)
3.b Ternary CH refined with riding coordinates:
 C17(H17)
3.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2A), C1(H1), C5(H5), C4(H4), C3(H3A), C12(H12), C19(H19), C21(H21),
 C22(H22), C24(H24), C25(H25)
3.e Fitted hexagon refined as free rotating group:
 C2(C1,C6,C5,C4,C3)
3.f Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
3.g Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O6(H6)
;
_shelx_res_checksum              33653
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.159
_oxdiff_exptl_absorpt_empirical_full_min 0.841