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_7234673
_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         '2(C9 H17 N5 S)'
_chemical_formula_sum            'C18 H34 N10 S2'
_chemical_formula_weight         454.67
_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             2019-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-05 deposited with the CCDC.    2019-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.617(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.018(4)
_cell_length_b                   22.054(6)
_cell_length_c                   9.300(3)
_cell_measurement_reflns_used    5225
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.61
_cell_measurement_theta_min      2.70
_cell_volume                     2414.4(13)
_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      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1074
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            50224
_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         26.372
_diffrn_reflns_theta_min         2.900
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1395 before and 0.0680 after correction. The Ratio of minimum to maximum transmission is 0.7967. The \l/2 correction factor is Not present.'
_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    1.251
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4917
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0561
_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^)+(0.0697P)^2^+2.7924P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1604
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3360
_reflns_number_total             4917
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc02439e2.cif
_cod_data_source_block           amt_120k
_cod_original_cell_volume        2414.5(12)
_cod_database_code               7234673
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.995
_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,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C4B-C1 \\sim C5B-C4B
 with sigma of 0.02
3. Rigid bond restraints
 C6A, C8A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C5AB) = Uanis(C5AA)
5. Rigid body (RIGU) restrains
 C4A, C5AB
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1, C4B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C8A, C6A, C7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: H4BA(0.7) H4BB(0.7) H4BC(0.3) H4BD(0.3) H4AC(0.3) H4AD(0.3)
 H4AA(0.7) H4AB(0.7) C5B(0.7) H5BA(0.7) H5BB(0.7) H5BC(0.7) C5AB(0.3) H5AA(0.3)
 H5AB(0.3) H5AC(0.3) C1(0.3) H1A(0.3) H1B(0.3) H1C(0.3) C5AA(0.7) H5AD(0.7)
 H5AE(0.7) H5AF(0.7)
7.a Ternary CH refined with riding coordinates:
 C6B(H6B), C6A(H6A)
7.b Secondary CH2 refined with riding coordinates:
 C4B(H4BA,H4BB), C4B(H4BC,H4BD), C4A(H4AC,H4AD), C4A(H4AA,H4AB)
7.c Aromatic/amide H refined with riding coordinates:
 N4A(H4A), N4B(H4B), N2B(H2B), N2A(H2A)
7.d Idealised Me refined as rotating group:
 C9B(H9BA,H9BB,H9BC), C7A(H7AA,H7AB,H7AC), C7B(H7BA,H7BB,H7BC), C8B(H8BA,H8BB,
 H8BC), C9A(H9AA,H9AB,H9AC), C5B(H5BA,H5BB,H5BC), C8A(H8AA,H8AB,H8AC),
 C5AB(H5AA,H5AB,H5AC), C1(H1A,H1B,H1C), C5AA(H5AD,H5AE,H5AF)
;
_shelx_res_checksum              21010
_olex2_submission_special_instructions 'No special instructions were received'