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_7242799
_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         'C9 H18 N5 S, N O3'
_chemical_formula_sum            'C9 H18 N6 O3 S'
_chemical_formula_weight         290.35
_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             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                77.541(7)
_cell_angle_beta                 72.346(7)
_cell_angle_gamma                67.479(7)
_cell_formula_units_Z            2
_cell_length_a                   9.1659(7)
_cell_length_b                   9.5067(8)
_cell_length_c                   9.6825(8)
_cell_measurement_reflns_used    15139
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.719
_cell_measurement_theta_min      3.401
_cell_volume                     737.89(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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15139
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.719
_diffrn_reflns_theta_min         3.401
_exptl_absorpt_coefficient_mu    0.234
_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    1.307
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0657
_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^)+(0.0828P)^2^+0.3629P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1805
_refine_ls_wR_factor_ref         0.1950
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2250
_reflns_number_total             3125
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00356a2.cif
_cod_data_source_block           amt_no3
_cod_depositor_comments
'Adding full bibliography for 7242798--7242801.cif.'
_cod_original_cell_volume        737.90(11)
_cod_database_code               7242799
_shelx_shelxl_version_number     2014/7
_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
2. Restrained distances
 C4A-C5A
 1.51 with sigma of 0.02
 C4A-C5A \\sim C5B-C4B
 with sigma of 0.02
 N5B-C4A \\sim N5A-C4B
 with sigma of 0.02
 N5A-C3 \\sim N5B-C3
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N5B, C4A, C5A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N5A, C5B, C4B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N4, C1, N1, C2, N3, C3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: N5A(0.45) H5A(0.45) C5A(0.55) H5AA(0.55) H5AB(0.55) H5AC(0.55)
 C5B(0.45) H5BA(0.45) H5BB(0.45) H5BC(0.45) C4A(0.55) H4AA(0.55) H4AB(0.55)
 C4B(0.45) H4BA(0.45) H4BB(0.45) N5B(0.55) H5B(0.55)
5.a Ternary CH refined with riding coordinates:
 C6(H6)
5.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C4B(H4BA,H4BB)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N5A(H5A), N5B(H5B)
5.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C), C5A(H5AA,H5AB,H5AC),
 C5B(H5BA,H5BB,H5BC)
;
_olex2_submission_original_sample_id 'Ametryn nitrate'
_olex2_submission_special_instructions 'No special instructions were received'