#------------------------------------------------------------------------------
#$Date: 2022-10-11 00:58:07 +0300 (Tue, 11 Oct 2022) $
#$Revision: 278513 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/08/7130837.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_7130837
loop_
_publ_author_name
'Lin, Bo'
'Yao, Yunfei'
'Huang, Yangjie'
'Lin, Qi'
'Weng, Zhiqiang'
_publ_section_title
;
 Regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles via
 photocycloaddition of sydnone with CF3CN
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03928A
_journal_year                    2022
_chemical_formula_moiety         'C9 H5 F3 N2 O'
_chemical_formula_sum            'C9 H5 F3 N2 O'
_chemical_formula_weight         214.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-02-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-08 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.245(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.5653(19)
_cell_length_b                   4.4815(5)
_cell_length_c                   24.060(2)
_cell_measurement_reflns_used    3620
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      66.81
_cell_measurement_theta_min      3.68
_cell_volume                     1890.9(3)
_computing_cell_refinement       lb20201022
_computing_data_reduction        lb20201022
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6581
_diffrn_reflns_theta_full        66.51
_diffrn_reflns_theta_max         66.51
_diffrn_reflns_theta_min         3.68
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.251
_exptl_absorpt_correction_T_max  0.9401
_exptl_absorpt_correction_T_min  0.8851
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0778
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1027P)²+3.8934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2165
_refine_ls_wR_factor_ref         0.2352
_reflns_number_gt                1206
_reflns_number_total             1610
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc03928a2.cif
_cod_data_source_block           11
_cod_database_code               7130837
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O001 O 0.76854(14) 0.5746(7) 0.65461(10) 0.0566(8) Uani 1 d . . .
F002 F 0.84354(15) 0.7226(8) 0.50328(10) 0.0867(10) Uani 1 d . . .
F003 F 0.95193(14) 0.7353(8) 0.54494(13) 0.0966(11) Uani 1 d . . .
N004 N 0.79290(17) 0.6087(8) 0.60053(12) 0.0541(9) Uani 1 d . . .
F005 F 0.8863(3) 1.1273(7) 0.53654(14) 0.1300(16) Uani 1 d . . .
N006 N 0.45948(19) -0.2877(10) 0.67943(15) 0.0716(11) Uani 1 d . . .
C007 C 0.70573(19) 0.3878(9) 0.65630(15) 0.0497(9) Uani 1 d . . .
C008 C 0.5134(2) -0.1480(10) 0.67532(16) 0.0562(10) Uani 1 d . . .
C009 C 0.58037(19) 0.0339(9) 0.66911(15) 0.0503(10) Uani 1 d . . .
C00A C 0.8489(2) 0.7809(9) 0.60030(17) 0.0558(10) Uani 1 d . . .
H00A H 0.8688 0.8684 0.6330 0.067 Uiso 1 calc . . R
C00B C 0.6716(2) 0.2472(10) 0.61029(15) 0.0541(10) Uani 1 d . . .
H00B H 0.6906 0.2717 0.5753 0.065 Uiso 1 calc . . R
C00C C 0.6086(2) 0.0690(10) 0.61745(16) 0.0544(10) Uani 1 d . . .
H00C H 0.5851 -0.0282 0.5869 0.065 Uiso 1 calc . . R
C00D C 0.6777(2) 0.3537(10) 0.70852(16) 0.0560(10) Uani 1 d . . .
H00D H 0.7010 0.4516 0.7390 0.067 Uiso 1 calc . . R
C00E C 0.6155(2) 0.1750(10) 0.71510(16) 0.0572(11) Uani 1 d . . .
H00E H 0.5970 0.1485 0.7502 0.069 Uiso 1 calc . . R
C00F C 0.8828(2) 0.8416(10) 0.54623(19) 0.0625(11) Uani 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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C007 O001 N004 112.2(3) . . ?
C00A N004 O001 110.7(3) . . ?
C00B C007 O001 124.2(3) . . ?
C00B C007 C00D 121.1(4) . . ?
C00D C007 O001 114.7(3) . . ?
N006 C008 C009 178.5(5) . . ?
C00C C009 C008 119.7(3) . . ?
C00C C009 C00E 120.1(4) . . ?
C00E C009 C008 120.2(3) . . ?
N004 C00A H00A 120.9 . . ?
N004 C00A C00F 118.1(4) . . ?
C00F C00A H00A 120.9 . . ?
C007 C00B H00B 120.7 . . ?
C007 C00B C00C 118.5(3) . . ?
C00C C00B H00B 120.7 . . ?
C009 C00C C00B 120.8(4) . . ?
C009 C00C H00C 119.6 . . ?
C00B C00C H00C 119.6 . . ?
C007 C00D H00D 120.1 . . ?
C00E C00D C007 119.8(4) . . ?
C00E C00D H00D 120.1 . . ?
C009 C00E H00E 120.2 . . ?
C00D C00E C009 119.7(3) . . ?
C00D C00E H00E 120.2 . . ?
F002 C00F C00A 113.2(4) . . ?
F003 C00F F002 106.2(4) . . ?
F003 C00F C00A 111.9(4) . . ?
F005 C00F F002 106.5(4) . . ?
F005 C00F F003 107.5(4) . . ?
F005 C00F C00A 111.2(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
O001 N004 1.401(4) . ?
O001 C007 1.387(4) . ?
F002 C00F 1.322(5) . ?
F003 C00F 1.307(5) . ?
N004 C00A 1.250(5) . ?
F005 C00F 1.304(5) . ?
N006 C008 1.144(5) . ?
C007 C00B 1.381(5) . ?
C007 C00D 1.384(5) . ?
C008 C009 1.446(5) . ?
C009 C00C 1.373(5) . ?
C009 C00E 1.389(6) . ?
C00A H00A 0.9300 . ?
C00A C00F 1.486(6) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.383(5) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00E 1.370(5) . ?
C00E H00E 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
O001 N004 C00A C00F 179.6(3) . . . . ?
O001 C007 C00B C00C -179.3(3) . . . . ?
O001 C007 C00D C00E 179.7(4) . . . . ?
N004 O001 C007 C00B 1.0(5) . . . . ?
N004 O001 C007 C00D -178.0(3) . . . . ?
N004 C00A C00F F002 6.0(6) . . . . ?
N004 C00A C00F F003 -113.9(5) . . . . ?
N004 C00A C00F F005 125.8(5) . . . . ?
N006 C008 C009 C00C -60(18) . . . . ?
N006 C008 C009 C00E 119(18) . . . . ?
C007 O001 N004 C00A 179.2(3) . . . . ?
C007 C00B C00C C009 0.3(6) . . . . ?
C007 C00D C00E C009 -1.1(6) . . . . ?
C008 C009 C00C C00B 178.5(4) . . . . ?
C008 C009 C00E C00D -178.2(4) . . . . ?
C00B C007 C00D C00E 0.7(6) . . . . ?
C00C C009 C00E C00D 1.2(6) . . . . ?
C00D C007 C00B C00C -0.3(6) . . . . ?
C00E C009 C00C C00B -0.8(6) . . . . ?
