#------------------------------------------------------------------------------
#$Date: 2022-01-06 23:14:58 +0200 (Thu, 06 Jan 2022) $
#$Revision: 271839 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/39/7243946.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7243946
loop_
_publ_author_name
'Ito, Sho'
'White, Fraser J.'
'Okunishi, Eiji'
'Aoyama, Yoshitaka'
'Yamano, Akihito'
'Sato, Hiroyasu'
'Ferrara, Joseph D.'
'Jasnowski, Michał'
'Meyer, Mathias'
_publ_section_title
;
 Structure determination of small molecule compounds by an electron
 diffractometer for 3D ED/MicroED
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              8622
_journal_page_last               8630
_journal_paper_doi               10.1039/D1CE01172C
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C12 H8 F3 N5 O3 S'
_chemical_formula_sum            'C12 H8 F3 N5 O3 S'
_chemical_formula_weight         359.29
_chemical_name_systematic
N-(2,6-difluorophenyl)-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide
_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
_audit_creation_date             2021-07-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                115.25(6)
_cell_angle_beta                 91.67(5)
_cell_angle_gamma                95.51(4)
_cell_formula_units_Z            2
_cell_length_a                   8.302(3)
_cell_length_b                   10.025(6)
_cell_length_c                   10.638(6)
_cell_measurement_reflns_used    314
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.7568
_cell_measurement_theta_min      0.1105
_cell_volume                     794.7(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.763
_diffrn_measured_fraction_theta_max 0.763
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  40.00   1.00    5.00    --    0.00   0.00   0.00   65
  2  ω    -30.00  40.00   1.00    5.00    --    0.00   0.00   0.00   70
  3  ω    -40.00  50.00   1.00    5.00    --    0.00   0.00   0.00   90
  4  ω    -10.00  40.00   1.00    5.00    --    0.00   0.00   0.00   50
  5  ω    -25.00  50.00   1.00    5.00    --    0.00   0.00   0.00   75
  6  ω    -25.00  50.00   1.00    5.00    --    0.00   0.00   0.00   75
  7  ω    -40.00  30.00   1.00    5.00    --    0.00   0.00   0.00   70
  8  ω    -45.00  30.00   1.00    5.00    --    0.00   0.00   0.00   75
  9  ω    -35.00  18.00   1.00    5.00    --    0.00   0.00   0.00   53
 10  ω    -50.00  15.00   1.00    5.00    --    0.00   0.00   0.00   65
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0002675000
_diffrn_orient_matrix_UB_12      -0.0011818000
_diffrn_orient_matrix_UB_13      -0.0026164000
_diffrn_orient_matrix_UB_21      -0.0027171000
_diffrn_orient_matrix_UB_22      0.0009133000
_diffrn_orient_matrix_UB_23      0.0000343000
_diffrn_orient_matrix_UB_31      0.0013524000
_diffrn_orient_matrix_UB_32      0.0023546000
_diffrn_orient_matrix_UB_33      0.0000105000
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_reflns_av_R_equivalents  0.2081
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_Laue_measured_fraction_full 0.763
_diffrn_reflns_Laue_measured_fraction_max 0.763
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12066
_diffrn_reflns_point_group_measured_fraction_full 0.763
_diffrn_reflns_point_group_measured_fraction_max 0.763
_diffrn_reflns_theta_full        0.757
_diffrn_reflns_theta_max         0.757
_diffrn_reflns_theta_min         0.111
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.18a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_description       needle
_exptl_crystal_F_000             124
_exptl_crystal_recrystallization_method 'Re-crystallized on grid'
_exptl_crystal_size_max          0.0003
_exptl_crystal_size_mid          0.0003
_exptl_crystal_size_min          0.0003
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       898(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   2.269
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         1482
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.269
_refine_ls_R_factor_all          0.2143
_refine_ls_R_factor_gt           0.1602
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3630
_refine_ls_wR_factor_ref         0.3769
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1077
_reflns_number_total             1482
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01172c1.cif
_cod_data_source_block           group2
_cod_depositor_comments
'Adding full bibliography for 7243939--7243951.cif.'
_cod_original_cell_volume        794.6(8)
_cod_database_code               7243946
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H8 F3 N5 O3 S'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 77.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.76
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N17(H17), C9(H9), C11(H11), C4(H4), C10(H10)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.741
_oxdiff_exptl_absorpt_empirical_full_min 0.394
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S24 S 0.7309(5) 0.5472(6) 0.3754(9) 0.037(3) Uani 1 1 d . . . . .
N15 N 0.9300(11) 0.6826(14) 0.748(2) 0.057(6) Uani 1 1 d . . . . .
C2 C 0.8093(16) 0.5757(19) 0.747(3) 0.066(8) Uani 1 1 d . . . . .
N16 N 0.9254(10) 0.6843(12) 0.618(2) 0.048(6) Uani 1 1 d . . . . .
C1 C 0.8041(10) 0.5802(12) 0.546(2) 0.058(7) Uani 1 1 d . . . . .
N17 N 0.6031(11) 0.6695(12) 0.4015(17) 0.048(5) Uani 1 1 d . . . . .
H17 H 0.501647 0.639214 0.377426 0.058 Uiso 1 1 calc R U . . .
C7 C 0.6585(11) 0.8318(15) 0.466(2) 0.048(7) Uani 1 1 d . . . . .
C5 C 1.0417(16) 0.7687(18) 0.856(2) 0.056(7) Uani 1 1 d . . . . .
N13 N 0.7271(12) 0.5048(15) 0.613(2) 0.044(5) Uani 1 1 d . . . . .
O19 O 0.8715(10) 0.5849(13) 0.3114(18) 0.055(5) Uani 1 1 d . . . . .
O20 O 0.6393(12) 0.3979(12) 0.305(2) 0.075(7) Uani 1 1 d . . . . .
O18 O 1.1461(14) 0.8665(18) 0.845(3) 0.087(8) Uani 1 1 d . . . . .
C9 C 0.7349(14) 1.0703(15) 0.667(3) 0.093(10) Uani 1 1 d . . . . .
H9 H 0.735587 1.128583 0.762314 0.112 Uiso 1 1 calc R U . . .
C3 C 0.7982(18) 0.5570(19) 0.873(3) 0.068(8) Uani 1 1 d . . . . .
F23 F 0.6170(14) 0.8536(14) 0.692(2) 0.067(6) Uani 1 1 d . . . . .
N14 N 1.0350(14) 0.7513(17) 0.971(3) 0.104(10) Uani 1 1 d . . . . .
C8 C 0.6702(13) 0.9215(16) 0.611(2) 0.052(7) Uani 1 1 d . . . . .
C12 C 0.7133(13) 0.8940(17) 0.368(3) 0.063(8) Uani 1 1 d . . . . .
C6 C 1.275(2) 0.947(2) 0.941(3) 0.095(9) Uani 1 1 d . . . . .
H6A H 1.332189 1.015222 0.912019 0.143 Uiso 1 1 calc R U . . .
H6B H 1.346426 0.880663 0.948452 0.143 Uiso 1 1 calc R U . . .
H6C H 1.234410 1.001522 1.030689 0.143 Uiso 1 1 calc R U . . .
C11 C 0.7881(15) 1.0481(18) 0.437(3) 0.070(9) Uani 1 1 d . . . . .
H11 H 0.831477 1.093463 0.383481 0.084 Uiso 1 1 calc R U . . .
F21 F 0.6861(14) 0.4495(16) 0.877(2) 0.090(8) Uani 1 1 d . . . . .
C4 C 0.9153(19) 0.648(2) 0.985(3) 0.102(11) Uani 1 1 d . . . . .
H4 H 0.913520 0.639486 1.068836 0.122 Uiso 1 1 calc R U . . .
C10 C 0.7968(15) 1.1309(19) 0.584(3) 0.081(9) Uani 1 1 d . . . . .
H10 H 0.845929 1.228615 0.624566 0.097 Uiso 1 1 calc R U . . .
F22 F 0.697(2) 0.811(2) 0.234(3) 0.103(10) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N17 S24 C1 104.1(8) . . ?
O19 S24 C1 105.8(7) . . ?
O19 S24 N17 109.0(6) . . ?
O19 S24 O20 119.2(10) . . ?
O20 S24 C1 109.7(8) . . ?
O20 S24 N17 108.0(6) . . ?
C2 N15 N16 109.2(18) . . ?
C5 N15 C2 127(2) . . ?
C5 N15 N16 124.2(12) . . ?
N15 C2 N13 108.8(17) . . ?
N15 C2 C3 117(2) . . ?
N13 C2 C3 134.5(14) . . ?
C1 N16 N15 103.2(12) . . ?
N16 C1 S24 122.5(11) . . ?
N16 C1 N13 117.1(18) . . ?
N13 C1 S24 120.2(11) . . ?
S24 N17 H17 119.2 . . ?
C7 N17 S24 121.6(7) . . ?
C7 N17 H17 119.2 . . ?
N17 C7 C12 115.6(19) . . ?
C8 C7 N17 123.4(14) . . ?
C8 C7 C12 120.8(14) . . ?
O18 C5 N15 121(2) . . ?
O18 C5 N14 122(2) . . ?
N14 C5 N15 117.5(15) . . ?
C1 N13 C2 101.7(12) . . ?
C5 O18 C6 125(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C10 C9 C8 121(2) . . ?
F21 C3 C2 120(2) . . ?
F21 C3 C4 124(2) . . ?
C4 C3 C2 116.3(16) . . ?
C5 N14 C4 122(2) . . ?
C9 C8 C7 121.4(17) . . ?
F23 C8 C7 116.2(13) . . ?
F23 C8 C9 122(2) . . ?
C11 C12 C7 114(2) . . ?
F22 C12 C7 120.0(16) . . ?
F22 C12 C11 126.3(19) . . ?
O18 C6 H6A 109.5 . . ?
O18 C6 H6B 109.5 . . ?
O18 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C11 H11 119.0 . . ?
C10 C11 C12 122.0(18) . . ?
C10 C11 H11 119.0 . . ?
C3 C4 H4 119.5 . . ?
N14 C4 C3 121(2) . . ?
N14 C4 H4 119.5 . . ?
C9 C10 C11 121.2(16) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S24 C1 1.777(19) . ?
S24 N17 1.638(10) . ?
S24 O19 1.467(11) . ?
S24 O20 1.473(13) . ?
N15 C2 1.390(17) . ?
N15 N16 1.40(2) . ?
N15 C5 1.36(3) . ?
C2 N13 1.41(3) . ?
C2 C3 1.43(3) . ?
N16 C1 1.327(18) . ?
C1 N13 1.371(17) . ?
N17 H17 0.8600 . ?
N17 C7 1.488(18) . ?
C7 C8 1.41(2) . ?
C7 C12 1.49(2) . ?
C5 O18 1.289(18) . ?
C5 N14 1.31(3) . ?
O18 C6 1.38(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.39(2) . ?
C9 C10 1.35(2) . ?
C3 F21 1.372(18) . ?
C3 C4 1.43(3) . ?
F23 C8 1.37(2) . ?
N14 C4 1.42(2) . ?
C12 C11 1.46(2) . ?
C12 F22 1.30(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C10 1.42(3) . ?
C4 H4 0.9300 . ?
C10 H10 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S24 C1 N13 C2 -173.1(8) . . . . ?
S24 N17 C7 C8 -89.2(14) . . . . ?
S24 N17 C7 C12 86.6(15) . . . . ?
N15 C2 N13 C1 -1.8(13) . . . . ?
N15 C2 C3 F21 -177.4(11) . . . . ?
N15 C2 C3 C4 -1.6(18) . . . . ?
N15 N16 C1 S24 173.7(8) . . . . ?
N15 N16 C1 N13 -1.4(12) . . . . ?
N15 C5 O18 C6 -172.4(17) . . . . ?
N15 C5 N14 C4 -1(2) . . . . ?
C2 N15 N16 C1 0.1(12) . . . . ?
C2 N15 C5 O18 -178.6(12) . . . . ?
C2 N15 C5 N14 -1(2) . . . . ?
C2 C3 C4 N14 0(2) . . . . ?
N16 N15 C2 N13 1.2(14) . . . . ?
N16 N15 C2 C3 179.0(10) . . . . ?
N16 N15 C5 O18 5(2) . . . . ?
N16 N15 C5 N14 -177.5(12) . . . . ?
N16 C1 N13 C2 2.1(13) . . . . ?
C1 S24 N17 C7 65.8(15) . . . . ?
N17 S24 C1 N16 -83.9(10) . . . . ?
N17 S24 C1 N13 91.0(9) . . . . ?
N17 C7 C8 C9 174.8(8) . . . . ?
N17 C7 C8 F23 -4.3(15) . . . . ?
N17 C7 C12 C11 -171.6(9) . . . . ?
N17 C7 C12 F22 6.1(18) . . . . ?
C7 C12 C11 C10 -3.8(17) . . . . ?
C5 N15 C2 N13 -175.9(12) . . . . ?
C5 N15 C2 C3 1.9(19) . . . . ?
C5 N15 N16 C1 177.3(11) . . . . ?
C5 N14 C4 C3 1(2) . . . . ?
N13 C2 C3 F21 0(2) . . . . ?
N13 C2 C3 C4 175.6(15) . . . . ?
O19 S24 C1 N16 30.9(11) . . . . ?
O19 S24 C1 N13 -154.2(9) . . . . ?
O19 S24 N17 C7 -46.7(17) . . . . ?
O20 S24 C1 N16 160.7(9) . . . . ?
O20 S24 C1 N13 -24.4(11) . . . . ?
O20 S24 N17 C7 -177.6(15) . . . . ?
O18 C5 N14 C4 177.2(13) . . . . ?
C3 C2 N13 C1 -179.1(12) . . . . ?
N14 C5 O18 C6 10(3) . . . . ?
C8 C7 C12 C11 4.3(14) . . . . ?
C8 C7 C12 F22 -178.0(14) . . . . ?
C8 C9 C10 C11 4(2) . . . . ?
C12 C7 C8 C9 -0.8(16) . . . . ?
C12 C7 C8 F23 -179.8(9) . . . . ?
C12 C11 C10 C9 0(2) . . . . ?
F21 C3 C4 N14 176.0(12) . . . . ?
C10 C9 C8 C7 -3.7(17) . . . . ?
C10 C9 C8 F23 175.3(12) . . . . ?
F22 C12 C11 C10 178.6(17) . . . . ?
