Driving a sustainable application of s-triazine ametryn and atrazine herbicides through multicomponent crystals with improved solubility
da Silva, Amandha Kaiser; Diniz, Luan F.; Tenorio, Juan C.; Nazário, Carlos E. D.; Ribeiro, Caue; Carvalho Jr, Paulo S.; CrystEngComm 23 (2021) 4252–4263; doi:10.1039/D1CE00356A

data_7242798
_publ_section_title
;
 Driving a sustainable application of s-triazine ametryn and atrazine
 herbicides through multicomponent crystals with improved solubility
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              4252
_journal_page_last               4263
_journal_paper_doi               10.1039/D1CE00356A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C8 H14 Cl N5, C2 H2 O2, 0.11(H2 O)'
_chemical_formula_sum            'C10 H16.22 Cl N5 O2.11'
_chemical_formula_weight         275.71
_chemical_name_systematic        'Atrazine fumaric acid cocrystal'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-11-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-11-24 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.589(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.892(4)
_cell_length_b                   6.2547(15)
_cell_length_c                   24.173(6)
_cell_measurement_reflns_used    28552
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.730
_cell_measurement_theta_min      3.155
_cell_volume                     2764.3(11)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2164
_diffrn_reflns_av_unetI/netI     0.0811
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            28552
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.730
_diffrn_reflns_theta_min         3.155
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       prism
_exptl_crystal_F_000             1161
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.892
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2928
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0863
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+19.1131P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2048
_refine_ls_wR_factor_ref         0.2128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2470
_reflns_number_total             2928
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00356a2.cif
_cod_data_source_block           atz-fum_h2o
_cod_depositor_comments
'Adding full bibliography for 7242798--7242801.cif.'
_cod_database_code               7242798
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.940
_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, All O(H,H) groups
2. Rigid body (RIGU) restrains
 N4, N1, C2, C3, C1, N3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: OW1(0.11) HW1A(0.11) HW1B(0.11)
4.a Free rotating group:
 OW1(HW1A,HW1B)
4.b Ternary CH refined with riding coordinates:
 C6(H6)
4.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
4.d Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), C10(H10)
4.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C5(H5A,H5B,H5C)
4.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;