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_7234674
_publ_section_title
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 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 H18 N5 S), 2(C4 H3 O4)'
_chemical_formula_sum            'C26 H42 N10 O8 S2'
_chemical_formula_weight         686.81
_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                 95.693(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.132(3)
_cell_length_b                   11.105(2)
_cell_length_c                   16.920(3)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.58
_cell_measurement_theta_min      2.42
_cell_volume                     3390.1(10)
_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_measured_fraction_theta_full 0.999
_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  0.0414
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            67624
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.258
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_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    1.346
_exptl_crystal_description       prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.121
_refine_diff_density_max         1.511
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     474
_refine_ls_number_reflns         6669
_refine_ls_number_restraints     130
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0950
_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^)+(0.0770P)^2^+15.1380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2327
_refine_ls_wR_factor_ref         0.2364
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6114
_reflns_number_total             6669
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc02439e2.cif
_cod_data_source_block           amt_fum_120k
_cod_database_code               7234674
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.942
_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. Restrained distances
 O3B'-H3B'
 0.95 with sigma of 0.02
 O3B-C0 \\sim O3B-C13B
 with sigma of 0.002
 N2B'-C3B \\sim N2B-C3B
 with sigma of 0.002
 C5B'-C4B' \\sim C5B-C4B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C3) = Uanis(C10B)
Uanis(O2B') = Uanis(O2B)
Uanis(O1B') = Uanis(O1B)
Uanis(C13B) = Uanis(C0)
Uanis(C5B') = Uanis(C5B)
Uanis(N2B') = Uanis(N2B)
Uanis(C013) = Uanis(C12B)
Uanis(O3B') = Uanis(O4B)
Uanis(C4) = Uanis(C11B)
4. Rigid body (RIGU) restrains
 N2B', C4B', C5B'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O3B', C0, C013, C4, C3, O2B', O1B'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1B, C1B, N3B, C2B, N5B, C3B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1B, C10B, O2B, C11B, C12B, C13B, O4B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2B, C4B, C5B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O1B(0.7) O2B(0.7) C0(0.3) C013(0.3) H013(0.3) O4B(0.7) H4BE(0.7)
 C10B(0.7) C12B(0.7) H12B(0.7) C4(0.3) H4(0.3) C11B(0.7) H11B(0.7) C3(0.3)
 O2B'(0.3) O1B'(0.3) C13B(0.7) O3B'(0.3) H3B'(0.3) H4AA(0.7) H4AB(0.7)
 H4AC(0.3) H4AD(0.3) C5A(0.7) H5AA(0.7) H5AB(0.7) H5AC(0.7) N2B'(0.3) H2B'(0.3)
 C1(0.3) H1A(0.3) H1B(0.3) H1C(0.3) C4B'(0.3) H4BA(0.3) H4BB(0.3) C5B(0.7)
 H5BA(0.7) H5BB(0.7) H5BC(0.7) C5B'(0.3) H5BD(0.3) H5BE(0.3) H5BF(0.3) C4B(0.7)
 H4BC(0.7) H4BD(0.7) N2B(0.7) H2B(0.7)
6.a Ternary CH refined with riding coordinates:
 C6A(H6A), C6B(H6B)
6.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C4A(H4AC,H4AD), C4B'(H4BA,H4BB), C4B(H4BC,H4BD)
6.c Aromatic/amide H refined with riding coordinates:
 N5A(H5A), N4A(H4A), N2A(H2A), N5B(H5B), N4B(H4B), C11A(H11A), C12A(H12A),
 C013(H013), C12B(H12B), C4(H4), C11B(H11B), N2B'(H2B'), N2B(H2B)
6.d Idealised Me refined as rotating group:
 C9B(H9BA,H9BB,H9BC), C8B(H8BA,H8BB,H8BC), C7A(H7AA,H7AB,H7AC), C9A(H9AA,H9AB,
 H9AC), C7B(H7BA,H7BB,H7BC), C8A(H8AA,H8AB,H8AC), C5A(H5AA,H5AB,H5AC), C1(H1A,
 H1B,H1C), C5B(H5BA,H5BB,H5BC), C5B'(H5BD,H5BE,H5BF)
6.e Idealised tetrahedral OH refined as rotating group:
 O4A(H4AE), O4B(H4BE), O3B'(H3B')
;
_shelx_res_checksum              48779
_olex2_submission_special_instructions 'No special instructions were received'