The crystal structure of 3,4-dihydroxybenzoic acid – 3-[7-{[2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylsulfanyl)-3H-[1,2,3] triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol – water (1/1/1), C30H36F2N6O9S
Xia, Ying-Fan; Lu, Rong-Bin; Sun, Wei-Jie; Lin, Shu-Ting; Zhang, Jia-Rong; Jiang, Cheng-Jun; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 331–333; doi:10.1515/ncrs-2022-0572

data_8107431
_publ_section_title
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 The crystal structure of 3,4-dihydroxybenzoic acid&#x00A0;--
 3-[7-{[2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylsulfanyl)-3H-[1,2,3]
 triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol
 -- water (1/1/1), C30H36F2N6O9S
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_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              331
_journal_page_last               333
_journal_paper_doi               10.1515/ncrs-2022-0572
_journal_volume                  238
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H28 F2 N6 O4 S, C7 H6 O4, H2 O'
_chemical_formula_sum            'C30 H36 F2 N6 O9 S'
_chemical_formula_weight         694.71
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2364(8)
_cell_length_b                   10.0250(14)
_cell_length_c                   59.689(9)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      59.010
_cell_measurement_theta_min      3.890
_cell_volume                     3133.4(8)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.10'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'zju Bruker D8 VENTURE'
_diffrn_measurement_method       '\? and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       76
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            32058
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         59.119
_diffrn_reflns_theta_min         2.576
_diffrn_source_current           3.58
_diffrn_source_power             0.2502778
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    1.029
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1318 before and 0.0875 after correction.
The Ratio of minimum to maximum transmission is 0.8359.
The \?/2 correction factor is Not present.
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_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       needle
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 2526 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.100(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         6747
_refine_ls_number_restraints     273
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0479P)^2^+0.8375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                6536
_reflns_number_total             6747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0572_suppl.cif
_cod_data_source_block           2
_cod_database_code               8107431
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.708
_olex2_refinement_description
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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. Restrained distances
 F2-C18 \\sim F2A-C18A
 with sigma of 0.02
 C14-C15 \\sim C14-C15A
 with sigma of 0.02
 C15-C16 \\sim C15A-C16A
 with sigma of 0.02
 C15-C20 \\sim C15A-C20A
 with sigma of 0.02
 C18-F1 \\sim C18A-F1A
 with sigma of 0.04
 C18-C17 \\sim C18A-C17A
 with sigma of 0.02
 C18-C19 \\sim C18A-C19A
 with sigma of 0.02
 C16-F1 \\sim C16A-F1A
 with sigma of 0.04
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 F1-C17 \\sim F1A-C17A
 with sigma of 0.02
 C18-C16 \\sim C18A-C16A
 with sigma of 0.04
 C18-C20 \\sim C18A-C20A
 with sigma of 0.04
 C20-C19 \\sim C20A-C19A
 with sigma of 0.02
 C16-C20 \\sim C16A-C20A
 with sigma of 0.04
 F2-C17 \\sim F2A-C17A
 with sigma of 0.04
 F2-C19 \\sim F2A-C19A
 with sigma of 0.04
 C17-C19 \\sim C17A-C19A
 with sigma of 0.04
 C14-C16 \\sim C14-C16A
 with sigma of 0.04
 C14-C20 \\sim C14-C20A
 with sigma of 0.04
 C15-C17 \\sim C15A-C17A
 with sigma of 0.04
 C15-C19 \\sim C15A-C19A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C14 \\sim F1 \\sim F2 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim
C20 \\sim F1A \\sim F2A \\sim C15A \\sim C16A \\sim C17A \\sim C18A \\sim C19A
\\sim C20A: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
4. Others
 Sof(H14A)=Sof(F1A)=Sof(F2A)=Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(C18A)=
 Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=1-FVAR(1)
 Sof(H14)=Sof(F1)=Sof(F2)=Sof(C15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(C18)=
 Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=FVAR(1)
5.a Free rotating group:
 O9(H9A,H9B)
5.b Ternary CH refined with riding coordinates:
 C3(H3A), C4(H4A), C5(H5), C6(H6A), C12(H12), C14(H14), C14(H14A)
5.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C7(H7A,H7B), C13(H13A,H13B), C21(H21A,H21B),
 C22(H22A,H22B)
5.d Aromatic/amide H refined with riding coordinates:
 N6(H6), C16(H16), C19(H19), C20(H20), C16A(H16A), C19A(H19A), C20A(H20A),
 C24(H24), C25(H25), C28(H28)
5.e Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
5.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4), O5(H5A), O6(H6B), O7(H7)
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_shelx_res_checksum              84495