#------------------------------------------------------------------------------
#$Date: 2015-08-27 13:20:27 +0200 (jue 27 de ago de 2015) $
#$Revision: 153724 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/76/7117639.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_7117639
loop_
_publ_author_name
'Yu-Tao He'
'Qiang Wang'
'Jiahui Zhao'
'Xue-Yuan Liu'
'Peng-Fei Xu'
'Yong-Min Liang'
_publ_section_title
;
 The copper-catalyzed synthesis of beta-trifluoromethylated acrylonitriles
 and trifluoromethyl-substituted 2H-azirines
;
_journal_name_full               Chem.Commun.
_journal_page_first              13209
_journal_paper_doi               10.1039/C5cc05066A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C15 H10 F3 N O'
_chemical_formula_sum            'C15 H10 F3 N O'
_chemical_formula_weight         277.24
_chemical_name_systematic
;
 ? 
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2015-06-19 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.84(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.226(3)
_cell_length_b                   13.605(4)
_cell_length_c                   7.270(2)
_cell_measurement_reflns_used    665
_cell_measurement_temperature    293.18(10)
_cell_measurement_theta_max      22.1390
_cell_measurement_theta_min      4.0760
_cell_volume                     1306.6(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.18(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega    7.00   37.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000    0.0000 15

  2 omega   -1.00   23.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -90.0000 12

  3 omega  -14.00   86.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416   19.0000   60.0000 50

  4 omega   -8.00   24.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  150.0000 16

  5 omega  -19.00   63.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -99.0000  120.0000 41

  6 omega  -46.00   42.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000 -120.0000 44

  7 omega   49.00   77.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  178.0000  -90.0000 14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0345076000
_diffrn_orient_matrix_UB_12      0.0127301000
_diffrn_orient_matrix_UB_13      0.0676844000
_diffrn_orient_matrix_UB_21      -0.0247523000
_diffrn_orient_matrix_UB_22      -0.0459124000
_diffrn_orient_matrix_UB_23      -0.0126971000
_diffrn_orient_matrix_UB_31      0.0329283000
_diffrn_orient_matrix_UB_32      -0.0210519000
_diffrn_orient_matrix_UB_33      0.0693409000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1576
_diffrn_reflns_av_unetI/netI     0.1566
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8091
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.2202
_refine_ls_R_factor_gt           0.1085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1865P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2646
_refine_ls_wR_factor_ref         0.3752
_reflns_number_gt                887
_reflns_number_total             2559
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05066a2.cif
_cod_data_source_block           wangq0518
_cod_original_cell_volume        1306.5(6)
_cod_database_code               7117639
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_date_sample_data_collection 2015-05-18
_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+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.8740(3) 0.7317(3) 0.5024(7) 0.0934(16) Uani 1 d . . .
F2 F 0.9567(4) 0.6188(4) 0.3730(8) 0.1170(19) Uani 1 d . . .
F3 F 1.0323(3) 0.7203(3) 0.5561(7) 0.1005(17) Uani 1 d . . .
O1 O 0.3157(3) 0.6505(3) 0.2388(6) 0.0591(13) Uani 1 d . . .
N1 N 0.8527(5) 0.4743(5) 1.0585(11) 0.082(2) Uani 1 d . . .
C1 C 0.7431(4) 0.5975(4) 0.6847(8) 0.0393(13) Uani 1 d . . .
C2 C 0.7117(4) 0.5758(4) 0.5066(9) 0.0444(14) Uani 1 d . . .
H2 H 0.7573 0.5481 0.4282 0.053 Uiso 1 calc . . R
C3 C 0.6098(4) 0.5950(3) 0.4391(8) 0.0415(14) Uani 1 d . . .
C4 C 0.5425(4) 0.6388(3) 0.5586(8) 0.0389(14) Uani 1 d . . .
C5 C 0.5768(4) 0.6596(4) 0.7441(8) 0.0421(14) Uani 1 d . . .
H5 H 0.5323 0.6870 0.8250 0.051 Uiso 1 calc . . R
C6 C 0.6737(4) 0.6399(4) 0.8033(9) 0.0465(15) Uani 1 d . . .
H6 H 0.6948 0.6547 0.9241 0.056 Uiso 1 calc . . R
C7 C 0.4400(3) 0.6566(4) 0.4965(8) 0.0425(14) Uani 1 d . . .
H7 H 0.3940 0.6824 0.5762 0.051 Uiso 1 calc . . R
C8 C 0.4102(4) 0.6348(4) 0.3157(8) 0.0439(15) Uani 1 d . . .
C9 C 0.4780(4) 0.5921(4) 0.1991(9) 0.0475(15) Uani 1 d . . .
H9 H 0.4565 0.5767 0.0788 0.057 Uiso 1 calc . . R
C10 C 0.5744(4) 0.5726(4) 0.2569(8) 0.0481(15) Uani 1 d . . .
H10 H 0.6181 0.5441 0.1760 0.058 Uiso 1 calc . . R
C11 C 0.2414(4) 0.6932(5) 0.3533(11) 0.075(2) Uani 1 d . . .
H11A H 0.1784 0.7004 0.2832 0.113 Uiso 1 calc . . GR
H11B H 0.2645 0.7565 0.3961 0.113 Uiso 1 calc . . GR
H11C H 0.2318 0.6511 0.4570 0.113 Uiso 1 calc . . GR
C12 C 0.8463(4) 0.5744(4) 0.7572(9) 0.0538(17) Uani 1 d . . .
C13 C 0.9347(5) 0.6016(5) 0.6918(11) 0.0621(19) Uani 1 d . . .
H13 H 0.9931 0.5772 0.7518 0.075 Uiso 1 calc . . R
C14 C 0.9480(4) 0.6676(6) 0.5317(13) 0.075(2) Uani 1 d . . .
C15 C 0.8520(5) 0.5179(5) 0.9259(13) 0.066(2) 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 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C8 O1 C11 117.7(5) . .
C2 C1 C6 119.2(4) . .
C2 C1 C12 121.6(5) . .
C6 C1 C12 119.2(5) . .
C1 C2 H2 119.4 . .
C1 C2 C3 121.2(5) . .
C3 C2 H2 119.4 . .
C4 C3 C2 118.6(5) . .
C4 C3 C10 118.6(5) . .
C10 C3 C2 122.9(5) . .
C3 C4 C5 119.1(4) . .
C3 C4 C7 119.8(5) . .
C7 C4 C5 121.0(5) . .
C4 C5 H5 119.7 . .
C6 C5 C4 120.7(5) . .
C6 C5 H5 119.7 . .
C1 C6 H6 119.4 . .
C5 C6 C1 121.2(5) . .
C5 C6 H6 119.4 . .
C4 C7 H7 120.5 . .
C8 C7 C4 119.0(5) . .
C8 C7 H7 120.5 . .
O1 C8 C7 124.7(5) . .
O1 C8 C9 115.0(5) . .
C9 C8 C7 120.4(5) . .
C8 C9 H9 119.3 . .
C10 C9 C8 121.3(5) . .
C10 C9 H9 119.3 . .
C3 C10 H10 119.5 . .
C9 C10 C3 120.9(6) . .
C9 C10 H10 119.5 . .
O1 C11 H11A 109.5 . .
O1 C11 H11B 109.5 . .
O1 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 C1 128.7(6) . .
C13 C12 C15 116.0(6) . .
C15 C12 C1 115.2(6) . .
C12 C13 H13 117.1 . .
C12 C13 C14 125.8(6) . .
C14 C13 H13 117.1 . .
F1 C14 F2 106.5(6) . .
F1 C14 F3 106.0(6) . .
F1 C14 C13 114.2(6) . .
F2 C14 C13 113.1(6) . .
F3 C14 F2 105.9(7) . .
F3 C14 C13 110.6(6) . .
N1 C15 C12 177.4(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C14 1.320(7) .
F2 C14 1.341(9) .
F3 C14 1.331(7) .
O1 C8 1.361(6) .
O1 C11 1.441(8) .
N1 C15 1.132(9) .
C1 C2 1.372(8) .
C1 C6 1.414(8) .
C1 C12 1.472(7) .
C2 H2 0.9300 .
C2 C3 1.435(7) .
C3 C4 1.407(8) .
C3 C10 1.416(8) .
C4 C5 1.430(8) .
C4 C7 1.429(7) .
C5 H5 0.9300 .
C5 C6 1.358(7) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C7 C8 1.385(8) .
C8 C9 1.392(8) .
C9 H9 0.9300 .
C9 C10 1.348(7) .
C10 H10 0.9300 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C13 1.336(9) .
C12 C15 1.446(11) .
C13 H13 0.9300 .
C13 C14 1.487(11) .
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
O1 C8 C9 C10 179.8(5) . . . .
C1 C2 C3 C4 1.3(8) . . . .
C1 C2 C3 C10 -179.3(5) . . . .
C1 C12 C13 C14 3.4(11) . . . .
C1 C12 C15 N1 -10(17) . . . .
C2 C1 C6 C5 0.0(8) . . . .
C2 C1 C12 C13 55.8(9) . . . .
C2 C1 C12 C15 -127.0(6) . . . .
C2 C3 C4 C5 -2.0(7) . . . .
C2 C3 C4 C7 -178.5(5) . . . .
C2 C3 C10 C9 -179.9(5) . . . .
C3 C4 C5 C6 1.7(8) . . . .
C3 C4 C7 C8 -3.3(8) . . . .
C4 C3 C10 C9 -0.5(8) . . . .
C4 C5 C6 C1 -0.7(8) . . . .
C4 C7 C8 O1 -178.3(4) . . . .
C4 C7 C8 C9 2.9(8) . . . .
C5 C4 C7 C8 -179.7(5) . . . .
C6 C1 C2 C3 -0.3(8) . . . .
C6 C1 C12 C13 -126.4(7) . . . .
C6 C1 C12 C15 50.8(7) . . . .
C7 C4 C5 C6 178.2(5) . . . .
C7 C8 C9 C10 -1.3(8) . . . .
C8 C9 C10 C3 0.0(9) . . . .
C10 C3 C4 C5 178.6(5) . . . .
C10 C3 C4 C7 2.1(7) . . . .
C11 O1 C8 C7 0.2(8) . . . .
C11 O1 C8 C9 179.1(5) . . . .
C12 C1 C2 C3 177.5(5) . . . .
C12 C1 C6 C5 -177.9(5) . . . .
C12 C13 C14 F1 27.9(11) . . . .
C12 C13 C14 F2 -94.1(8) . . . .
C12 C13 C14 F3 147.4(7) . . . .
C13 C12 C15 N1 168(17) . . . .
C15 C12 C13 C14 -173.8(6) . . . .
