#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:30:52 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268944 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158166.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_7158166
loop_
_publ_author_name
'Kobayashi, Yusuke'
'Masakado, Sota'
'Murai, Takuya'
'Hamada, Shohei'
'Furuta, Takumi'
'Takemoto, Yoshiji'
_publ_section_title
;
 A bench-stable N-trifluoroacetyl nitrene equivalent for a simple
 synthesis of 2-trifluoromethyl oxazoles.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6628
_journal_page_last               6632
_journal_paper_doi               10.1039/d1ob00947h
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C8 H4 F3 I N2 O3'
_chemical_formula_sum            'C8 H4 F3 I N2 O3'
_chemical_formula_weight         360.03
_chemical_melting_point          118.0(10)
_chemical_name_systematic        SM569
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-12
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_audit_update_record
;
2021-04-27 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.298(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9637(2)
_cell_length_b                   20.0442(7)
_cell_length_c                   10.3335(4)
_cell_measurement_reflns_used    4927
_cell_measurement_temperature    93
_cell_measurement_theta_max      72.8460
_cell_measurement_theta_min      4.4010
_cell_volume                     1008.19(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_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      93
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00  90.00   0.50    0.50    --    0.90  29.00 120.00  356
  2  ω    -84.00 -38.00   0.50    1.04    --    5.00  60.00   0.00   92
  3  ω   -188.00 -35.00   0.50    1.04    --  -98.40  57.00  90.00  306
  4  ω   -188.00 -35.00   0.50    1.04    --  -98.40  57.00  60.00  306
  5  ω   -188.00  -9.00   0.50    1.04    --  -98.40  43.00 150.00  358
  6  ω   -188.00 -35.00   0.50    1.04    --  -98.40  57.00  60.00  306
  7  ω   -188.00 -38.00   0.50    1.04    --  -98.40  60.00 150.00  300
  8  ω   -188.00 -38.00   0.50    1.04    --  -98.40  60.00   0.00  300
  9  ω    -90.00 -38.00   0.50    0.50    --   -0.90  60.00  90.00  104
 10  ω   -188.00-110.00   0.50    1.04    --  -98.40   0.00 150.00  156
 11  ω   -188.00  -9.00   0.50    1.04    --  -98.40   0.00   0.00  358
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0165057000
_diffrn_orient_matrix_UB_12      -0.0653566000
_diffrn_orient_matrix_UB_13      0.0796123000
_diffrn_orient_matrix_UB_21      -0.0346352000
_diffrn_orient_matrix_UB_22      -0.0404306000
_diffrn_orient_matrix_UB_23      -0.1289541000
_diffrn_orient_matrix_UB_31      0.3142264000
_diffrn_orient_matrix_UB_32      -0.0010419000
_diffrn_orient_matrix_UB_33      0.0115457000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9201
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.260
_diffrn_reflns_theta_min         4.412
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    25.461
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    2.372
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_preparation       condensation
_exptl_crystal_recrystallization_method pyridine-ether
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         3.497
_refine_diff_density_min         -3.623
_refine_diff_density_rms         0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0641
_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/[σ²(Fo²)+(0.1324P)²+3.8932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1774
_refine_ls_wR_factor_ref         0.1789
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1908
_reflns_number_total             1959
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00947h2.cif
_cod_data_source_block           exp_218
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '117-119' was changed to
'118.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158166.cif.
;
_cod_database_code               7158166
_chemical_oxdiff_formula         'C20 H16 F12 I4 N20 O12 '
_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 99.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C4(H4), C3(H3)
;
_shelx_shelxl_version_number     2016/6
_olex2_exptl_crystal_mounting_method loop
_olex2_submission_original_sample_id SM569
_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 8.300
_oxdiff_exptl_absorpt_empirical_full_min 0.555
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_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
I7 I 0.53740(9) 0.38428(2) 0.47071(4) 0.0265(3) Uani 1 1 d . . . . .
F13 F 1.0963(12) 0.4471(3) 0.1789(6) 0.0424(12) Uani 1 1 d . . . . .
F11 F 0.7302(12) 0.5024(3) 0.1035(5) 0.0456(12) Uani 1 1 d . . . . .
F12 F 1.0492(14) 0.5465(3) 0.2492(6) 0.0520(15) Uani 1 1 d . . . . .
O17 O 0.2414(11) 0.3186(3) 0.6188(5) 0.0317(11) Uani 1 1 d . . . . .
O16 O 0.1610(12) 0.2165(3) 0.6668(6) 0.0363(13) Uani 1 1 d . . . . .
O14 O 0.6705(17) 0.5062(3) 0.3862(7) 0.0480(18) Uani 1 1 d . . . . .
N15 N 0.2733(13) 0.2574(3) 0.6082(6) 0.0272(13) Uani 1 1 d . . . . .
N8 N 0.7680(14) 0.3994(3) 0.3310(6) 0.0278(13) Uani 1 1 d . . . . .
C2 C 0.4522(13) 0.2349(4) 0.5222(6) 0.0248(16) Uani 1 1 d . . . . .
C1 C 0.5863(15) 0.2805(3) 0.4536(7) 0.0217(13) Uani 1 1 d . . . . .
C5 C 0.7828(15) 0.1880(4) 0.3578(7) 0.0273(15) Uani 1 1 d . . . . .
H5 H 0.897184 0.171440 0.301334 0.033 Uiso 1 1 calc R . . . .
C6 C 0.7515(15) 0.2564(4) 0.3694(7) 0.0235(14) Uani 1 1 d . . . . .
H6 H 0.841316 0.286386 0.320583 0.028 Uiso 1 1 calc R . . . .
C4 C 0.6518(15) 0.1435(4) 0.4262(7) 0.0244(14) Uani 1 1 d . . . . .
H4 H 0.675438 0.096875 0.416080 0.029 Uiso 1 1 calc R . . . .
C3 C 0.4867(16) 0.1665(4) 0.5093(8) 0.0290(16) Uani 1 1 d . . . . .
H3 H 0.397269 0.135958 0.557207 0.035 Uiso 1 1 calc R . . . .
C10 C 0.9196(18) 0.4893(4) 0.2150(8) 0.0335(16) Uani 1 1 d . . . . .
C9 C 0.7751(17) 0.4646(4) 0.3226(8) 0.0314(16) 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 0.0181 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'
I I -0.3257 6.8362 '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
N8 I7 C1 89.9(3) . . ?
O17 N15 C2 117.8(6) . . ?
O16 N15 O17 122.8(7) . . ?
O16 N15 C2 119.4(7) . . ?
C9 N8 I7 102.8(5) . . ?
C1 C2 N15 121.1(7) . . ?
C3 C2 N15 117.9(7) . . ?
C3 C2 C1 121.0(7) . . ?
C2 C1 I7 121.8(6) . . ?
C6 C1 I7 119.1(5) . . ?
C6 C1 C2 119.0(6) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.5(7) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.1(7) . . ?
C5 C6 H6 120.5 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.1(7) . . ?
C3 C4 H4 119.9 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.3(8) . . ?
C4 C3 H3 120.4 . . ?
F13 C10 F11 105.7(6) . . ?
F13 C10 F12 108.3(7) . . ?
F13 C10 C9 115.6(6) . . ?
F11 C10 C9 109.6(7) . . ?
F12 C10 F11 106.1(6) . . ?
F12 C10 C9 111.1(7) . . ?
O14 C9 N8 128.1(8) . . ?
O14 C9 C10 118.5(7) . . ?
N8 C9 C10 113.3(7) . . ?
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
I7 N8 2.033(7) . ?
I7 C1 2.106(6) . ?
F13 C10 1.324(10) . ?
F11 C10 1.362(10) . ?
F12 C10 1.329(9) . ?
O17 N15 1.244(9) . ?
O16 N15 1.218(9) . ?
O14 C9 1.237(9) . ?
N15 C2 1.446(9) . ?
N8 C9 1.310(11) . ?
C2 C1 1.401(10) . ?
C2 C3 1.392(12) . ?
C1 C6 1.394(11) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(10) . ?
C5 C4 1.378(10) . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.377(12) . ?
C3 H3 0.9500 . ?
C10 C9 1.520(12) . ?
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
I7 N8 C9 O14 1.2(11) . . . . ?
I7 N8 C9 C10 -175.4(6) . . . . ?
I7 C1 C6 C5 -179.8(5) . . . . ?
F13 C10 C9 O14 159.9(8) . . . . ?
F13 C10 C9 N8 -23.1(10) . . . . ?
F11 C10 C9 O14 -80.8(9) . . . . ?
F11 C10 C9 N8 96.1(8) . . . . ?
F12 C10 C9 O14 36.1(11) . . . . ?
F12 C10 C9 N8 -147.0(7) . . . . ?
O17 N15 C2 C1 0.3(9) . . . . ?
O17 N15 C2 C3 -179.5(6) . . . . ?
O16 N15 C2 C1 -179.6(6) . . . . ?
O16 N15 C2 C3 0.5(10) . . . . ?
N15 C2 C1 I7 0.0(8) . . . . ?
N15 C2 C1 C6 -178.5(6) . . . . ?
N15 C2 C3 C4 178.8(7) . . . . ?
C2 C1 C6 C5 -1.3(10) . . . . ?
C1 C2 C3 C4 -1.0(11) . . . . ?
C5 C4 C3 C2 0.6(11) . . . . ?
C6 C5 C4 C3 -0.5(11) . . . . ?
C4 C5 C6 C1 0.8(11) . . . . ?
C3 C2 C1 I7 179.8(5) . . . . ?
C3 C2 C1 C6 1.4(10) . . . . ?
