#------------------------------------------------------------------------------
#$Date: 2015-08-27 13:20:27 +0200 (jue 27 de ago de 2015) $
#$Revision: 153724 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/76/7117636.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_7117636
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         'C24 H22 F3 N O2'
_chemical_formula_sum            'C24 H22 F3 N O2'
_chemical_formula_weight         413.43
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-04
_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                 96.885(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   33.4249(17)
_cell_length_b                   6.2204(3)
_cell_length_c                   20.9937(9)
_cell_measurement_reflns_used    1352
_cell_measurement_temperature    293.6(2)
_cell_measurement_theta_max      21.7380
_cell_measurement_theta_min      3.8190
_cell_volume                     4333.5(4)
_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      293.6(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -18.00   15.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   60.0000 33

  2 omega  -49.00   44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000 -150.0000 93

  3 omega  -34.00   61.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000   90.0000 95
;
_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      0.0021901000
_diffrn_orient_matrix_UB_12      -0.0164466000
_diffrn_orient_matrix_UB_13      -0.0328351000
_diffrn_orient_matrix_UB_21      0.0160779000
_diffrn_orient_matrix_UB_22      -0.0725530000
_diffrn_orient_matrix_UB_23      0.0088462000
_diffrn_orient_matrix_UB_31      -0.0139197000
_diffrn_orient_matrix_UB_32      -0.0863998000
_diffrn_orient_matrix_UB_33      -0.0012025000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8148
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.32
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70281
_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    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0635
_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)+(0.0674P)²+0.9196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1951
_reflns_number_gt                2053
_reflns_number_total             4254
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05066a2.cif
_cod_data_source_block           heyt0504
_cod_original_cell_volume        4333.5(3)
_cod_database_code               7117636
_reflns_odcompleteness_completeness 99.67
_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. Uiso/Uaniso restraints and constraints
Uanis(F2') \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1') \\sim Ueq, Uanis(F1)
\\sim Ueq, Uanis(F3') \\sim Ueq, Uanis(F3) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F1'(0.5) F2'(0.5) F3'(0.5) C13'(0.5) H13A(0.5) H13B(0.5) H13C(0.5)
 C14'(0.5) H14A(0.5) H14B(0.5) H14C(0.5) C15'(0.5) H15A(0.5) H15B(0.5)
 H15C(0.5) C13(0.5) H2A(0.5) H2B(0.5) H2C(0.5) F2(0.5) C15(0.5) H3A(0.5)
 H3B(0.5) H3C(0.5) F1(0.5) F3(0.5) C14(0.5) H1B(0.5) H1A(0.5) H1C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C10(H10), C11(H11), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
4.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C13'(H13A,H13B,H13C), C14'(H14A,H14B,H14C), C15'(H15A,
 H15B,H15C), C13(H2A,H2B,H2C), C15(H3A,H3B,H3C), C14(H1B,H1A,H1C)
;
_olex2_date_sample_data_collection 2015-05-04
_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
_atom_site_refinement_flags_adp
O1 O 0.21528(7) 0.0609(3) 0.49731(11) 0.0781(7) Uani 1 d . . . .
O2 O 0.23570(6) 0.0477(3) 0.39990(10) 0.0644(6) Uani 1 d . . . .
N1 N 0.16500(7) 0.3962(4) 0.45731(11) 0.0533(6) Uani 1 d . . . .
C1 C 0.14058(8) 0.5591(4) 0.43659(14) 0.0523(7) Uani 1 d . . . .
C2 C 0.14000(8) 0.6452(4) 0.37475(14) 0.0537(7) Uani 1 d A . . .
C3 C 0.16724(8) 0.5674(4) 0.33413(13) 0.0519(7) Uani 1 d . . . .
C4 C 0.19241(8) 0.4000(4) 0.35727(13) 0.0538(7) Uani 1 d . . . .
H4 H 0.2109 0.3433 0.3321 0.065 Uiso 1 calc . . R .
C5 C 0.18986(8) 0.3179(4) 0.41784(14) 0.0511(7) Uani 1 d . . . .
C6 C 0.11382(8) 0.6304(5) 0.48463(13) 0.0539(7) Uani 1 d . . . .
C7 C 0.11729(9) 0.8265(5) 0.51446(18) 0.0750(10) Uani 1 d . . . .
H7 H 0.1365 0.9240 0.5036 0.090 Uiso 1 calc . . R .
C8 C 0.09282(10) 0.8818(6) 0.56035(17) 0.0780(10) Uani 1 d . . . .
H8 H 0.0964 1.0148 0.5804 0.094 Uiso 1 calc . . R .
C9 C 0.06323(9) 0.7463(5) 0.57739(15) 0.0630(8) Uani 1 d B . . .
C10 C 0.06039(11) 0.5508(5) 0.54721(19) 0.0832(11) Uani 1 d . . . .
H10 H 0.0409 0.4542 0.5573 0.100 Uiso 1 calc . . R .
C11 C 0.08534(10) 0.4914(5) 0.50244(18) 0.0792(11) Uani 1 d . . . .
H11 H 0.0828 0.3552 0.4841 0.095 Uiso 1 calc . . R .
C12 C 0.03552(11) 0.8076(6) 0.6274(2) 0.0841(11) Uani 1 d . . . .
C16 C 0.10886(12) 0.8109(7) 0.35026(19) 0.0773(10) Uani 1 d . . . .
C17 C 0.17072(9) 0.6466(5) 0.26803(14) 0.0581(8) Uani 1 d . . . .
C18 C 0.18935(12) 0.8378(6) 0.25743(18) 0.0894(12) Uani 1 d . . . .
H18 H 0.1994 0.9238 0.2919 0.107 Uiso 1 calc . . R .
C19 C 0.19324(15) 0.9026(7) 0.1954(2) 0.1138(15) Uani 1 d . . . .
H19 H 0.2063 1.0314 0.1887 0.137 Uiso 1 calc . . R .
C20 C 0.17842(15) 0.7821(9) 0.1443(2) 0.1083(16) Uani 1 d . . . .
H20 H 0.1805 0.8283 0.1027 0.130 Uiso 1 calc . . R .
C21 C 0.16064(13) 0.5948(9) 0.1550(2) 0.1122(15) Uani 1 d . . . .
H21 H 0.1505 0.5105 0.1202 0.135 Uiso 1 calc . . R .
C22 C 0.15697(11) 0.5239(6) 0.21605(17) 0.0919(12) Uani 1 d . . . .
H22 H 0.1450 0.3914 0.2220 0.110 Uiso 1 calc . . R .
C23 C 0.21452(8) 0.1301(5) 0.44386(15) 0.0542(7) Uani 1 d . . . .
C24 C 0.26045(10) -0.1366(5) 0.41949(17) 0.0767(10) Uani 1 d . . . .
H24A H 0.2718 -0.1936 0.3831 0.115 Uiso 1 calc . . GR .
H24B H 0.2443 -0.2447 0.4367 0.115 Uiso 1 calc . . GR .
H24C H 0.2818 -0.0939 0.4517 0.115 Uiso 1 calc . . GR .
F1' F 0.0779(4) 0.820(2) 0.3803(5) 0.148(6) Uani 0.50 d A 2 . U
F2' F 0.1226(4) 0.993(2) 0.3416(6) 0.132(4) Uani 0.50 d A 2 . U
F3' F 0.0924(3) 0.7554(18) 0.2905(6) 0.109(4) Uani 0.50 d A 2 . U
C13' C 0.0564(4) 0.933(4) 0.6786(7) 0.152(7) Uani 0.50 d B 2 . .
H13A H 0.0805 0.8589 0.6958 0.229 Uiso 0.50 calc B 2 GR .
H13B H 0.0393 0.9520 0.7117 0.229 Uiso 0.50 calc B 2 GR .
H13C H 0.0632 1.0704 0.6624 0.229 Uiso 0.50 calc B 2 GR .
C14' C 0.0016(4) 0.946(3) 0.5880(6) 0.136(4) Uani 0.50 d B 2 . .
H14A H 0.0133 1.0741 0.5726 0.204 Uiso 0.50 calc B 2 GR .
H14B H -0.0184 0.9849 0.6152 0.204 Uiso 0.50 calc B 2 GR .
H14C H -0.0108 0.8639 0.5522 0.204 Uiso 0.50 calc B 2 GR .
C15' C 0.0148(7) 0.611(3) 0.6518(9) 0.152(6) Uani 0.50 d B 2 . .
H15A H 0.0014 0.5328 0.6161 0.228 Uiso 0.50 calc B 2 GR .
H15B H -0.0046 0.6570 0.6792 0.228 Uiso 0.50 calc B 2 GR .
H15C H 0.0345 0.5210 0.6756 0.228 Uiso 0.50 calc B 2 GR .
C13 C 0.0330(6) 1.0447(19) 0.6401(10) 0.154(5) Uani 0.50 d B 1 . .
H2A H 0.0592 1.0975 0.6567 0.231 Uiso 0.50 calc B 1 GR .
H2B H 0.0145 1.0699 0.6709 0.231 Uiso 0.50 calc B 1 GR .
H2C H 0.0238 1.1182 0.6008 0.231 Uiso 0.50 calc B 1 GR .
F2 F 0.1170(5) 1.005(2) 0.3792(6) 0.140(5) Uani 0.50 d A 1 . U
C15 C -0.0058(4) 0.725(4) 0.6141(10) 0.157(7) Uani 0.50 d B 1 . .
H3A H -0.0177 0.7759 0.5730 0.235 Uiso 0.50 calc B 1 GR .
H3B H -0.0215 0.7748 0.6467 0.235 Uiso 0.50 calc B 1 GR .
H3C H -0.0053 0.5708 0.6141 0.235 Uiso 0.50 calc B 1 GR .
F1 F 0.0734(3) 0.758(2) 0.3650(7) 0.116(4) Uani 0.50 d A 1 . U
F3 F 0.1039(4) 0.839(3) 0.2895(6) 0.163(6) Uani 0.50 d A 1 . U
C14 C 0.0539(5) 0.704(4) 0.6939(6) 0.167(7) Uani 0.50 d B 1 . .
H1B H 0.0360 0.7302 0.7256 0.251 Uiso 0.50 calc B 1 GR .
H1A H 0.0797 0.7680 0.7076 0.251 Uiso 0.50 calc B 1 GR .
H1C H 0.0571 0.5521 0.6887 0.251 Uiso 0.50 calc B 1 GR .
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
C23 O2 C24 116.3(2) . .
C5 N1 C1 118.3(2) . .
N1 C1 C2 122.0(3) . .
N1 C1 C6 113.3(2) . .
C2 C1 C6 124.6(3) . .
C1 C2 C3 119.5(3) . .
C1 C2 C16 120.6(3) . .
C3 C2 C16 119.9(3) . .
C2 C3 C17 125.4(3) . .
C4 C3 C2 117.1(3) . .
C4 C3 C17 117.5(2) . .
C3 C4 H4 120.1 . .
C5 C4 C3 119.8(3) . .
C5 C4 H4 120.1 . .
N1 C5 C4 123.2(3) . .
N1 C5 C23 114.6(3) . .
C4 C5 C23 122.2(3) . .
C7 C6 C1 123.3(3) . .
C7 C6 C11 117.4(3) . .
C11 C6 C1 119.2(3) . .
C6 C7 H7 119.5 . .
C6 C7 C8 121.1(3) . .
C8 C7 H7 119.5 . .
C7 C8 H8 118.9 . .
C9 C8 C7 122.2(3) . .
C9 C8 H8 118.9 . .
C8 C9 C12 122.6(3) . .
C10 C9 C8 115.8(3) . .
C10 C9 C12 121.7(3) . .
C9 C10 H10 118.7 . .
C9 C10 C11 122.6(3) . .
C11 C10 H10 118.7 . .
C6 C11 C10 120.9(3) . .
C6 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C9 C12 C14' 103.5(5) . .
C9 C12 C14 107.4(5) . .
C13' C12 C9 111.6(5) . .
C13' C12 C14' 110.5(9) . .
C13' C12 C15' 112.4(10) . .
C13' C12 C13 50.8(7) . .
C13' C12 C15 133.7(8) . .
C13' C12 C14 57.4(8) . .
C14' C12 C14 149.1(6) . .
C15' C12 C9 111.7(6) . .
C15' C12 C14' 106.7(9) . .
C15' C12 C14 61.6(8) . .
C13 C12 C9 114.7(5) . .
C13 C12 C14' 60.4(7) . .
C13 C12 C15' 133.6(7) . .
C13 C12 C14 105.3(9) . .
C15 C12 C9 114.6(7) . .
C15 C12 C14' 59.4(8) . .
C15 C12 C15' 47.8(8) . .
C15 C12 C13 107.8(9) . .
C15 C12 C14 106.3(10) . .
F1' C16 C2 115.3(6) . .
F1' C16 F3' 101.8(9) . .
F1' C16 F2 82.6(9) . .
F1' C16 F1 22.9(10) . .
F1' C16 F3 118.2(8) . .
F2' C16 C2 114.8(7) . .
F2' C16 F1' 111.7(10) . .
F2' C16 F3' 102.3(8) . .
F2' C16 F2 37.1(9) . .
F2' C16 F1 128.9(9) . .
F2' C16 F3 74.7(8) . .
F3' C16 C2 109.2(6) . .
F3' C16 F2 132.5(8) . .
F2 C16 C2 111.2(7) . .
F1 C16 C2 110.8(7) . .
F1 C16 F3' 82.8(8) . .
F1 C16 F2 104.9(9) . .
F3 C16 C2 115.7(6) . .
F3 C16 F3' 28.3(10) . .
F3 C16 F2 108.6(10) . .
F3 C16 F1 105.0(9) . .
C18 C17 C3 121.6(3) . .
C22 C17 C3 120.2(3) . .
C22 C17 C18 118.1(3) . .
C17 C18 H18 120.0 . .
C17 C18 C19 120.0(4) . .
C19 C18 H18 120.0 . .
C18 C19 H19 119.4 . .
C20 C19 C18 121.2(4) . .
C20 C19 H19 119.4 . .
C19 C20 H20 120.7 . .
C21 C20 C19 118.5(4) . .
C21 C20 H20 120.7 . .
C20 C21 H21 119.1 . .
C20 C21 C22 121.8(4) . .
C22 C21 H21 119.1 . .
C17 C22 C21 120.4(4) . .
C17 C22 H22 119.8 . .
C21 C22 H22 119.8 . .
O1 C23 O2 123.8(3) . .
O1 C23 C5 124.8(3) . .
O2 C23 C5 111.3(3) . .
O2 C24 H24A 109.5 . .
O2 C24 H24B 109.5 . .
O2 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C12 C13' H13A 109.5 . .
C12 C13' H13B 109.5 . .
C12 C13' H13C 109.5 . .
H13A C13' H13B 109.5 . .
H13A C13' H13C 109.5 . .
H13B C13' H13C 109.5 . .
C12 C14' H14A 109.5 . .
C12 C14' H14B 109.5 . .
C12 C14' H14C 109.5 . .
H14A C14' H14B 109.5 . .
H14A C14' H14C 109.5 . .
H14B C14' H14C 109.5 . .
C12 C15' H15A 109.5 . .
C12 C15' H15B 109.5 . .
C12 C15' H15C 109.5 . .
H15A C15' H15B 109.5 . .
H15A C15' H15C 109.5 . .
H15B C15' H15C 109.5 . .
C12 C13 H2A 109.5 . .
C12 C13 H2B 109.5 . .
C12 C13 H2C 109.5 . .
C12 C15 H3A 109.5 . .
C12 C15 H3B 109.5 . .
C12 C15 H3C 109.5 . .
C12 C14 H1B 109.5 . .
C12 C14 H1A 109.5 . .
C12 C14 H1C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C23 1.199(3) .
O2 C23 1.331(3) .
O2 C24 1.444(3) .
N1 C1 1.340(3) .
N1 C5 1.334(3) .
C1 C2 1.403(4) .
C1 C6 1.493(4) .
C2 C3 1.406(4) .
C2 C16 1.511(4) .
C3 C4 1.389(4) .
C3 C17 1.490(4) .
C4 H4 0.9300 .
C4 C5 1.382(4) .
C5 C23 1.495(4) .
C6 C7 1.370(4) .
C6 C11 1.371(4) .
C7 H7 0.9300 .
C7 C8 1.380(4) .
C8 H8 0.9300 .
C8 C9 1.379(4) .
C9 C10 1.370(4) .
C9 C12 1.529(4) .
C10 H10 0.9300 .
C10 C11 1.380(4) .
C11 H11 0.9300 .
C12 C13' 1.437(11) .
C12 C14' 1.577(11) .
C12 C15' 1.522(14) .
C12 C13 1.503(11) .
C12 C15 1.469(13) .
C12 C14 1.594(12) .
C16 F1' 1.276(11) .
C16 F2' 1.244(14) .
C16 F3' 1.354(12) .
C16 F2 1.364(14) .
C16 F1 1.304(12) .
C16 F3 1.278(12) .
C17 C18 1.373(4) .
C17 C22 1.366(4) .
C18 H18 0.9300 .
C18 C19 1.384(5) .
C19 H19 0.9300 .
C19 C20 1.353(6) .
C20 H20 0.9300 .
C20 C21 1.339(6) .
C21 H21 0.9300 .
C21 C22 1.375(5) .
C22 H22 0.9300 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C13' H13A 0.9600 .
C13' H13B 0.9600 .
C13' H13C 0.9600 .
C14' H14A 0.9600 .
C14' H14B 0.9600 .
C14' H14C 0.9600 .
C15' H15A 0.9600 .
C15' H15B 0.9600 .
C15' H15C 0.9600 .
C13 H2A 0.9600 .
C13 H2B 0.9600 .
C13 H2C 0.9600 .
C15 H3A 0.9600 .
C15 H3B 0.9600 .
C15 H3C 0.9600 .
C14 H1B 0.9600 .
C14 H1A 0.9600 .
C14 H1C 0.9600 .
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
N1 C1 C2 C3 -3.5(4) . . . .
N1 C1 C2 C16 172.9(3) . . . .
N1 C1 C6 C7 112.4(3) . . . .
N1 C1 C6 C11 -64.6(4) . . . .
N1 C5 C23 O1 -5.8(4) . . . .
N1 C5 C23 O2 174.0(2) . . . .
C1 N1 C5 C4 1.7(4) . . . .
C1 N1 C5 C23 -177.3(2) . . . .
C1 C2 C3 C4 2.8(4) . . . .
C1 C2 C3 C17 -178.6(3) . . . .
C1 C2 C16 F1' -18.9(10) . . . .
C1 C2 C16 F2' 113.1(8) . . . .
C1 C2 C16 F3' -132.8(6) . . . .
C1 C2 C16 F2 72.8(9) . . . .
C1 C2 C16 F1 -43.4(8) . . . .
C1 C2 C16 F3 -162.7(9) . . . .
C1 C6 C7 C8 -177.5(3) . . . .
C1 C6 C11 C10 179.3(3) . . . .
C2 C1 C6 C7 -69.8(4) . . . .
C2 C1 C6 C11 113.2(4) . . . .
C2 C3 C4 C5 0.0(4) . . . .
C2 C3 C17 C18 76.3(4) . . . .
C2 C3 C17 C22 -106.9(4) . . . .
C3 C2 C16 F1' 157.5(9) . . . .
C3 C2 C16 F2' -70.5(8) . . . .
C3 C2 C16 F3' 43.6(7) . . . .
C3 C2 C16 F2 -110.7(8) . . . .
C3 C2 C16 F1 133.0(7) . . . .
C3 C2 C16 F3 13.7(11) . . . .
C3 C4 C5 N1 -2.3(4) . . . .
C3 C4 C5 C23 176.6(3) . . . .
C3 C17 C18 C19 177.8(3) . . . .
C3 C17 C22 C21 -179.0(3) . . . .
C4 C3 C17 C18 -105.1(4) . . . .
C4 C3 C17 C22 71.7(4) . . . .
C4 C5 C23 O1 175.3(3) . . . .
C4 C5 C23 O2 -4.9(4) . . . .
C5 N1 C1 C2 1.3(4) . . . .
C5 N1 C1 C6 179.2(2) . . . .
C6 C1 C2 C3 178.8(3) . . . .
C6 C1 C2 C16 -4.8(5) . . . .
C6 C7 C8 C9 -1.6(6) . . . .
C7 C6 C11 C10 2.1(5) . . . .
C7 C8 C9 C10 1.8(5) . . . .
C7 C8 C9 C12 -179.0(4) . . . .
C8 C9 C10 C11 -0.1(6) . . . .
C8 C9 C12 C13' -36.0(12) . . . .
C8 C9 C12 C14' 82.8(8) . . . .
C8 C9 C12 C15' -162.8(11) . . . .
C8 C9 C12 C13 19.5(11) . . . .
C8 C9 C12 C15 145.0(12) . . . .
C8 C9 C12 C14 -97.1(11) . . . .
C9 C10 C11 C6 -1.9(6) . . . .
C10 C9 C12 C13' 143.2(12) . . . .
C10 C9 C12 C14' -98.0(8) . . . .
C10 C9 C12 C15' 16.4(12) . . . .
C10 C9 C12 C13 -161.3(11) . . . .
C10 C9 C12 C15 -35.7(13) . . . .
C10 C9 C12 C14 82.1(12) . . . .
C11 C6 C7 C8 -0.4(5) . . . .
C12 C9 C10 C11 -179.4(4) . . . .
C16 C2 C3 C4 -173.7(3) . . . .
C16 C2 C3 C17 5.0(5) . . . .
C17 C3 C4 C5 -178.8(3) . . . .
C17 C18 C19 C20 1.0(7) . . . .
C18 C17 C22 C21 -2.1(5) . . . .
C18 C19 C20 C21 -1.6(7) . . . .
C19 C20 C21 C22 0.4(7) . . . .
C20 C21 C22 C17 1.6(7) . . . .
C22 C17 C18 C19 0.9(5) . . . .
C24 O2 C23 O1 0.4(4) . . . .
C24 O2 C23 C5 -179.4(2) . . . .
