High water soluble agrichemicals by engineered organic salts for reducing adverse environmental impacts
de Sousa Carvalho, Jr., Paulo de Sousa; Guimarães, Gelton Geraldo Fernandes; Diniz, Luan Farinelli; Ellena, Javier A.; Ribeiro, Caue; Green Chemistry  (2019) –; doi:10.1039/C9GC02439E

data_7234677
_publ_section_title
;
 High water soluble agrichemicals by engineered organic salts for reducing
 adverse environmental impacts
;
_journal_name_full               'Green Chemistry'
_journal_paper_doi               10.1039/C9GC02439E
_journal_year                    2019
_chemical_formula_moiety         '3(C9 H18 N5 S), 3(C4 H3 O4)'
_chemical_formula_sum            'C39 H63 N15 O12 S3'
_chemical_formula_weight         1030.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-07-05 deposited with the CCDC.    2019-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.226(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.495(3)
_cell_length_b                   16.262(3)
_cell_length_c                   23.781(5)
_cell_measurement_reflns_used    101144
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.679
_cell_measurement_theta_min      2.490
_cell_volume                     5151.4(18)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.0
_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 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_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  0.0436
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            101144
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         2.490
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.99237
_exptl_absorpt_correction_T_min  0.96714
_exptl_absorpt_correction_type   multi-scan
_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    1.328
_exptl_crystal_description       prism
_exptl_crystal_F_000             2184
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.384
_refine_diff_density_min         -1.154
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     651
_refine_ls_number_reflns         9760
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0687P)^2^+9.4865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1531
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8031
_reflns_number_total             9760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc02439e2.cif
_cod_data_source_block           amt-mal
_cod_original_cell_volume        5151.4(17)
_cod_database_code               7234677
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 C6A, C8A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C6C, C7C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C5A') = Uanis(C5A)
Uanis(C5C') = Uanis(C5C)
Uanis(C7B) = Uanis(C8B)
Uanis(C8B') = Uanis(C7B')
Uanis(C7C) = Uanis(C8C)
Uanis(C7A) = Uanis(C8A)
4. Rigid body (RIGU) restrains
 C5A, C4A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4A, C5A'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4C, C5C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4C, C5C'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C5C', C5C, C4C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C5B, C4B, C5B'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C6C, C8C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C8A, C6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: H4CA(0.7) H4CB(0.7) H4CC(0.3) H4CD(0.3) H6BA(0.4) H6B(0.6)
 H4BA(0.55) H4BB(0.55) H4BC(0.45) H4BD(0.45) H4AC(0.45) H4AD(0.45) H4AA(0.55)
 H4AB(0.55) C8B'(0.4) H8BA(0.4) H8BB(0.4) H8BC(0.4) C5B(0.55) H5BA(0.55)
 H5BB(0.55) H5BC(0.55) C5A'(0.45) H5AA(0.45) H5AB(0.45) H5AC(0.45) C7B(0.6)
 H7BA(0.6) H7BB(0.6) H7BC(0.6) C5C(0.7) H5CA(0.7) H5CB(0.7) H5CC(0.7) C5A(0.55)
 H5AD(0.55) H5AE(0.55) H5AF(0.55) C5C'(0.3) H5CD(0.3) H5CE(0.3) H5CF(0.3)
 C5B'(0.45) H5BD(0.45) H5BE(0.45) H5BF(0.45) C7B'(0.4) H7BD(0.4) H7BE(0.4)
 H7BF(0.4) C8B(0.6) H8BD(0.6) H8BE(0.6) H8BF(0.6)
6.a Ternary CH refined with riding coordinates:
 C6C(H6C), C6A(H6A), C6B(H6BA), C6B(H6B)
6.b Secondary CH2 refined with riding coordinates:
 C4C(H4CA,H4CB), C4C(H4CC,H4CD), C4B(H4BA,H4BB), C4B(H4BC,H4BD), C4A(H4AC,
 H4AD), C4A(H4AA,H4AB)
6.c Aromatic/amide H refined with riding coordinates:
 N3C(H3C), N1B(H1B), N3A(H3A), C11B(H11B), C12A(H12A), C11C(H11C), N2C(H2C),
 N4B(H4B), N2A(H2A), N4C(H4C), C11A(H11A), N2B(H2B), N4A(H4A), C12C(H12C),
 C12B(H12B)
6.d Idealised Me refined as rotating group:
 C027(H02A,H02B,H02C), C9A(H9AA,H9AB,H9AC), C9B(H9BA,H9BB,H9BC), C8A(H8AA,H8AB,
 H8AC), C7C(H7CA,H7CB,H7CC), C7A(H7AA,H7AB,H7AC), C8C(H8CA,H8CB,H8CC),
 C8B'(H8BA,H8BB,H8BC), C5B(H5BA,H5BB,H5BC), C5A'(H5AA,H5AB,H5AC), C7B(H7BA,H7BB,
 H7BC), C5C(H5CA,H5CB,H5CC), C5A(H5AD,H5AE,H5AF), C5C'(H5CD,H5CE,H5CF),
 C5B'(H5BD,H5BE,H5BF), C7B'(H7BD,H7BE,H7BF), C8B(H8BD,H8BE,H8BF)
6.e Idealised tetrahedral OH refined as rotating group:
 O3C(H3CA), O3A(H3AA), O3B(H3B)
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_shelx_res_checksum              99885
_olex2_submission_special_instructions 'No special instructions were received'