#------------------------------------------------------------------------------
#$Date: 2022-10-26 00:58:50 +0300 (Wed, 26 Oct 2022) $
#$Revision: 278781 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/09/7130900.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_7130900
loop_
_publ_author_name
'O'Hagan, David'
'Yu, Cihang'
'Cormanich, Rodrigo A.'
'Slawin, Alexandra'
'Cordes, David Bradford'
'Piscelli, Bruno A.'
'Al-Maharik, Nawaf'
_publ_section_title
;
 Unexpected triaxial preferences in some all-syn
 1,3,5-trifluorocyclohexanes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC05058G
_journal_year                    2022
_chemical_formula_moiety         'C11 H18 F3 N O2'
_chemical_formula_sum            'C11 H18 F3 N O2'
_chemical_formula_weight         253.26
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2022-08-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-19 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                95.696(4)
_cell_angle_beta                 96.546(5)
_cell_angle_gamma                98.362(5)
_cell_formula_units_Z            4
_cell_length_a                   6.2763(4)
_cell_length_b                   9.5541(4)
_cell_length_c                   21.1552(10)
_cell_measurement_reflns_used    3208
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.7310
_cell_measurement_theta_min      4.9220
_cell_volume                     1238.20(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011  (Burla et al.,  2007)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ      0.00 200.00   0.50   10.00   0.00 -30.00   0.00    --   400
  2  ω    -72.00   1.00   0.50   10.00    --  -30.00 -72.00 -90.00  146
  3  ω   -113.00 -71.00   0.50   10.00    --  -30.00 180.00 -45.00   84
  4  φ      0.00 200.00   0.50   10.00   0.00 -67.00   0.00    --   400
  5  ω    -85.00 -13.00   0.50   10.00    --  -67.00  72.00  90.00  144
  6  ω   -133.00 -93.00   0.50   10.00    --  -67.00 180.00   0.00   80
  7  ω    -85.00 -12.00   0.50   10.00    --  -67.00  72.00 -90.00  146
  8  ω   -126.00 -86.00   0.50   10.00    --  -67.00 180.00-180.00   80
  9  φ      0.00 200.00   0.50   10.00 -25.00-110.00   0.00    --   400
 10  ω   -128.00 -20.00   0.50   10.00    -- -110.00  72.00-135.00  216
 11  ω   -128.00 -20.00   0.50   10.00    -- -110.00  72.00  45.00  216
 12  ω   -115.00 -20.00   0.50   10.00    -- -110.00  72.00 -45.00  190
 13  ω   -113.00 -23.00   0.50   10.00    -- -110.00  72.00 135.00  180
 14  ω   -141.00 -46.00   0.50   10.00    -- -110.00 180.00 -90.00  190
 15  ω   -141.00 -46.00   0.50   10.00    -- -110.00 180.00-180.00  190
 16  ω   -141.00 -59.00   0.50   10.00    -- -110.00 180.00  90.00  164
 17  ω   -141.00 -55.00   0.50   10.00    -- -110.00 180.00   0.00  172
 18  ω   -141.00 -59.00   0.50   10.00    -- -110.00 180.00  45.00  164
 19  ω   -141.00 -78.00   0.50   10.00    -- -110.00 180.00 -45.00  126
 20  ω   -140.00 -77.00   0.50   10.00    -- -110.00 180.00-135.00  126
 21  ω   -140.00 -56.00   0.50   10.00    -- -110.00 180.00 135.00  168
;
_diffrn_measurement_device       'AFC12: Kappa 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1551216000
_diffrn_orient_matrix_UB_12      0.0984653000
_diffrn_orient_matrix_UB_13      0.0532045000
_diffrn_orient_matrix_UB_21      0.0474240000
_diffrn_orient_matrix_UB_22      0.1090514000
_diffrn_orient_matrix_UB_23      -0.0475748000
_diffrn_orient_matrix_UB_31      -0.1905372000
_diffrn_orient_matrix_UB_32      0.0731322000
_diffrn_orient_matrix_UB_33      0.0188270000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25453
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         2.117
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_exptl_absorpt_coefficient_mu    1.058
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
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    1.359
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone/dichloromethane'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         8795
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.852
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0774P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4680
_reflns_number_total             8795
_reflns_threshold_expression     'I > 2σ(I)'
_twin_special_details
;
Component 2 rotated by 16.8755° 
 around [-0.34 -0.91 0.24] (reciprocal) or [-0.71 -0.70 -0.02] (direct)
;
_cod_data_source_file            d2cc05058g2.cif
_cod_data_source_block           10
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7130900
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4988(11)
 0.5012(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N7-H7 = N27-H27
 0.98 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C6(H6), C21(H21), C22(H22), C24(H24), C26(H26)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C23(H23A,H23B), C25(H25A,H25B)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C)
;
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
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
F2 F 0.5908(3) 0.59908(18) 0.32910(9) 0.0485(5) Uani 1 1 d . . . . .
F4 F 0.5054(3) 0.65221(19) 0.46000(9) 0.0524(5) Uani 1 1 d . . . . .
F6 F 0.1905(3) 0.69004(18) 0.35568(9) 0.0485(5) Uani 1 1 d . . . . .
F22 F 0.3018(3) 0.21450(19) 0.38774(9) 0.0476(5) Uani 1 1 d . . . . .
F24 F -0.1080(3) 0.1571(2) 0.43770(9) 0.0555(5) Uani 1 1 d . . . . .
F26 F -0.0475(3) 0.06917(18) 0.30403(10) 0.0512(5) Uani 1 1 d . . . . .
O8 O 0.3849(4) 0.9981(2) 0.22151(11) 0.0473(6) Uani 1 1 d . . . . .
O9 O 0.2281(4) 0.7974(2) 0.15498(10) 0.0463(6) Uani 1 1 d . . . . .
O28 O 0.2638(3) 0.4798(2) 0.21110(10) 0.0392(5) Uani 1 1 d . . . . .
O29 O 0.4790(3) 0.3173(2) 0.18433(10) 0.0430(6) Uani 1 1 d . . . . .
N7 N 0.3880(5) 0.7768(3) 0.25146(13) 0.0412(7) Uani 1 1 d D . . . .
H7 H 0.332(5) 0.681(3) 0.2392(15) 0.058(11) Uiso 1 1 d D . . . .
N27 N 0.2556(4) 0.2744(3) 0.25701(13) 0.0378(6) Uani 1 1 d D . . . .
H27 H 0.307(5) 0.189(3) 0.2553(14) 0.041(9) Uiso 1 1 d D . . . .
C1 C 0.4851(5) 0.8264(3) 0.31648(15) 0.0366(7) Uani 1 1 d . . . . .
H1 H 0.552859 0.927775 0.316389 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6683(5) 0.7477(3) 0.33811(15) 0.0386(8) Uani 1 1 d . . . . .
H2 H 0.786851 0.767790 0.310880 0.046 Uiso 1 1 calc R U . . .
C3 C 0.7622(5) 0.7914(3) 0.40770(15) 0.0415(8) Uani 1 1 d . . . . .
H3A H 0.861029 0.724581 0.420740 0.050 Uiso 1 1 calc R U . . .
H3B H 0.849965 0.887489 0.411567 0.050 Uiso 1 1 calc R U . . .
C4 C 0.5944(5) 0.7941(3) 0.45329(16) 0.0416(8) Uani 1 1 d . . . . .
H4 H 0.666939 0.842172 0.496067 0.050 Uiso 1 1 calc R U . . .
C5 C 0.4118(5) 0.8715(3) 0.43088(15) 0.0419(8) Uani 1 1 d . . . . .
H5A H 0.295153 0.854012 0.458279 0.050 Uiso 1 1 calc R U . . .
H5B H 0.466610 0.975078 0.436937 0.050 Uiso 1 1 calc R U . . .
C6 C 0.3158(5) 0.8289(3) 0.36208(15) 0.0395(8) Uani 1 1 d . . . . .
H6 H 0.217759 0.897831 0.349300 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3355(5) 0.8684(3) 0.21025(15) 0.0383(8) Uani 1 1 d . . . . .
C10 C 0.1551(6) 0.8731(4) 0.10179(16) 0.0476(9) Uani 1 1 d . . . . .
C11 C -0.0022(8) 0.9677(5) 0.1219(2) 0.0979(18) Uani 1 1 d . . . . .
H11A H -0.115891 0.912668 0.141533 0.147 Uiso 1 1 calc R U . . .
H11B H -0.068242 1.005535 0.084304 0.147 Uiso 1 1 calc R U . . .
H11C H 0.074891 1.046820 0.153017 0.147 Uiso 1 1 calc R U . . .
C12 C 0.0414(7) 0.7533(4) 0.05123(17) 0.0654(11) Uani 1 1 d . . . . .
H12A H 0.141188 0.686041 0.042471 0.098 Uiso 1 1 calc R U . . .
H12B H -0.003752 0.793006 0.011774 0.098 Uiso 1 1 calc R U . . .
H12C H -0.086719 0.703732 0.066822 0.098 Uiso 1 1 calc R U . . .
C13 C 0.3503(7) 0.9540(5) 0.0773(2) 0.0951(17) Uani 1 1 d . . . . .
H13A H 0.420897 1.032293 0.109777 0.143 Uiso 1 1 calc R U . . .
H13B H 0.302103 0.992641 0.037824 0.143 Uiso 1 1 calc R U . . .
H13C H 0.453633 0.889196 0.068451 0.143 Uiso 1 1 calc R U . . .
C21 C 0.1119(5) 0.3113(3) 0.30244(15) 0.0353(7) Uani 1 1 d . . . . .
H21 H 0.068634 0.403630 0.291628 0.042 Uiso 1 1 calc R U . . .
C22 C 0.2236(5) 0.3401(3) 0.37118(15) 0.0386(8) Uani 1 1 d . . . . .
H22 H 0.349843 0.418397 0.373862 0.046 Uiso 1 1 calc R U . . .
C23 C 0.0753(5) 0.3822(3) 0.41854(15) 0.0429(8) Uani 1 1 d . . . . .
H23A H 0.048377 0.480176 0.413299 0.051 Uiso 1 1 calc R U . . .
H23B H 0.150305 0.383503 0.462431 0.051 Uiso 1 1 calc R U . . .
C24 C -0.1407(5) 0.2849(3) 0.41177(17) 0.0434(8) Uani 1 1 d . . . . .
H24 H -0.241069 0.332845 0.436849 0.052 Uiso 1 1 calc R U . . .
C25 C -0.2458(5) 0.2481(3) 0.34288(16) 0.0438(8) Uani 1 1 d . . . . .
H25A H -0.367604 0.168689 0.341086 0.053 Uiso 1 1 calc R U . . .
H25B H -0.308124 0.331375 0.329205 0.053 Uiso 1 1 calc R U . . .
C26 C -0.0976(5) 0.2061(3) 0.29568(16) 0.0389(8) Uani 1 1 d . . . . .
H26 H -0.174693 0.203071 0.251383 0.047 Uiso 1 1 calc R U . . .
C28 C 0.3284(5) 0.3672(3) 0.21696(14) 0.0336(7) Uani 1 1 d . . . . .
C30 C 0.5941(5) 0.4057(3) 0.14117(16) 0.0438(8) Uani 1 1 d . . . . .
C31 C 0.4341(6) 0.4383(5) 0.08762(17) 0.0716(12) Uani 1 1 d . . . . .
H31A H 0.341209 0.349807 0.067816 0.107 Uiso 1 1 calc R U . . .
H31B H 0.513472 0.481687 0.055339 0.107 Uiso 1 1 calc R U . . .
H31C H 0.343956 0.504432 0.105028 0.107 Uiso 1 1 calc R U . . .
C32 C 0.7483(6) 0.3117(4) 0.11602(18) 0.0598(11) Uani 1 1 d . . . . .
H32A H 0.842493 0.287039 0.152084 0.090 Uiso 1 1 calc R U . . .
H32B H 0.837526 0.362919 0.087924 0.090 Uiso 1 1 calc R U . . .
H32C H 0.664486 0.224428 0.091815 0.090 Uiso 1 1 calc R U . . .
C33 C 0.7229(6) 0.5395(4) 0.17984(18) 0.0549(10) Uani 1 1 d . . . . .
H33A H 0.623315 0.603913 0.192597 0.082 Uiso 1 1 calc R U . . .
H33B H 0.824207 0.586912 0.153745 0.082 Uiso 1 1 calc R U . . .
H33C H 0.804569 0.514017 0.218195 0.082 Uiso 1 1 calc R U . . .
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'
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'
F F 0.0727 0.0534 '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
C8 O9 C10 121.2(2) . . ?
C28 O29 C30 120.5(2) . . ?
C1 N7 H7 121(2) . . ?
C8 N7 H7 117(2) . . ?
C8 N7 C1 121.3(3) . . ?
C21 N27 H27 121.7(19) . . ?
C28 N27 H27 117.0(19) . . ?
C28 N27 C21 121.2(3) . . ?
N7 C1 H1 106.2 . . ?
N7 C1 C2 112.3(3) . . ?
N7 C1 C6 111.8(3) . . ?
C2 C1 H1 106.2 . . ?
C2 C1 C6 113.6(3) . . ?
C6 C1 H1 106.2 . . ?
F2 C2 C1 109.1(2) . . ?
F2 C2 H2 108.5 . . ?
F2 C2 C3 109.0(2) . . ?
C1 C2 H2 108.5 . . ?
C1 C2 C3 113.0(3) . . ?
C3 C2 H2 108.5 . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 C2 114.3(3) . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
F4 C4 C3 108.9(2) . . ?
F4 C4 H4 108.8 . . ?
F4 C4 C5 108.6(3) . . ?
C3 C4 H4 108.8 . . ?
C3 C4 C5 112.9(3) . . ?
C5 C4 H4 108.8 . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 C4 114.5(3) . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
F6 C6 C1 108.0(2) . . ?
F6 C6 C5 109.4(3) . . ?
F6 C6 H6 108.7 . . ?
C1 C6 H6 108.7 . . ?
C5 C6 C1 113.3(3) . . ?
C5 C6 H6 108.7 . . ?
O8 C8 O9 125.4(3) . . ?
O8 C8 N7 124.0(3) . . ?
N7 C8 O9 110.5(3) . . ?
O9 C10 C11 110.2(3) . . ?
O9 C10 C12 103.1(3) . . ?
O9 C10 C13 109.9(3) . . ?
C11 C10 C12 110.5(3) . . ?
C11 C10 C13 112.8(4) . . ?
C12 C10 C13 110.0(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N27 C21 H21 105.9 . . ?
N27 C21 C22 113.0(2) . . ?
N27 C21 C26 113.1(3) . . ?
C22 C21 H21 105.9 . . ?
C26 C21 H21 105.9 . . ?
C26 C21 C22 112.2(3) . . ?
F22 C22 C21 108.3(2) . . ?
F22 C22 H22 108.8 . . ?
F22 C22 C23 108.9(2) . . ?
C21 C22 H22 108.8 . . ?
C23 C22 C21 113.1(3) . . ?
C23 C22 H22 108.8 . . ?
C22 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
C22 C23 C24 114.2(3) . . ?
H23A C23 H23B 107.6 . . ?
C24 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
F24 C24 C23 108.7(3) . . ?
F24 C24 H24 108.7 . . ?
F24 C24 C25 108.8(3) . . ?
C23 C24 H24 108.7 . . ?
C23 C24 C25 113.1(3) . . ?
C25 C24 H24 108.7 . . ?
C24 C25 H25A 108.4 . . ?
C24 C25 H25B 108.4 . . ?
H25A C25 H25B 107.5 . . ?
C26 C25 C24 115.4(3) . . ?
C26 C25 H25A 108.4 . . ?
C26 C25 H25B 108.4 . . ?
F26 C26 C21 109.1(2) . . ?
F26 C26 C25 110.1(3) . . ?
F26 C26 H26 108.5 . . ?
C21 C26 H26 108.5 . . ?
C25 C26 C21 112.1(3) . . ?
C25 C26 H26 108.5 . . ?
O28 C28 O29 125.0(3) . . ?
O28 C28 N27 124.1(3) . . ?
O29 C28 N27 110.9(2) . . ?
O29 C30 C31 110.2(3) . . ?
O29 C30 C32 103.1(2) . . ?
O29 C30 C33 109.4(3) . . ?
C31 C30 C32 111.6(3) . . ?
C31 C30 C33 112.4(3) . . ?
C33 C30 C32 109.7(3) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
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
F2 C2 1.419(3) . ?
F4 C4 1.416(3) . ?
F6 C6 1.426(3) . ?
F22 C22 1.421(3) . ?
F24 C24 1.419(3) . ?
F26 C26 1.413(3) . ?
O8 C8 1.225(4) . ?
O9 C8 1.346(4) . ?
O9 C10 1.463(4) . ?
O28 C28 1.216(3) . ?
O29 C28 1.346(3) . ?
O29 C30 1.482(3) . ?
N7 H7 0.93(2) . ?
N7 C1 1.443(4) . ?
N7 C8 1.343(4) . ?
N27 H27 0.92(2) . ?
N27 C21 1.444(4) . ?
N27 C28 1.354(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.516(4) . ?
C1 C6 1.516(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.516(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.508(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.509(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.503(4) . ?
C6 H6 1.0000 . ?
C10 C11 1.500(5) . ?
C10 C12 1.519(5) . ?
C10 C13 1.522(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 H21 1.0000 . ?
C21 C22 1.521(4) . ?
C21 C26 1.518(4) . ?
C22 H22 1.0000 . ?
C22 C23 1.507(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.511(4) . ?
C24 H24 1.0000 . ?
C24 C25 1.515(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.505(4) . ?
C26 H26 1.0000 . ?
C30 C31 1.513(5) . ?
C30 C32 1.517(4) . ?
C30 C33 1.516(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N7 H7 O28 0.93(2) 1.92(2) 2.848(3) 171(3) . yes
N27 H27 O8 0.92(2) 2.04(2) 2.926(3) 162(3) 1_545 yes
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
F2 C2 C3 C4 -73.3(3) . . . . ?
F4 C4 C5 C6 -73.0(3) . . . . ?
F22 C22 C23 C24 -71.4(3) . . . . ?
F24 C24 C25 C26 -75.1(3) . . . . ?
N7 C1 C2 F2 -54.7(3) . . . . ?
N7 C1 C2 C3 -176.1(3) . . . . ?
N7 C1 C6 F6 55.2(3) . . . . ?
N7 C1 C6 C5 176.5(3) . . . . ?
N27 C21 C22 F22 -60.6(3) . . . . ?
N27 C21 C22 C23 178.6(3) . . . . ?
N27 C21 C26 F26 58.6(3) . . . . ?
N27 C21 C26 C25 -179.2(3) . . . . ?
C1 N7 C8 O8 8.0(5) . . . . ?
C1 N7 C8 O9 -173.8(3) . . . . ?
C1 C2 C3 C4 48.2(4) . . . . ?
C2 C1 C6 F6 -73.2(3) . . . . ?
C2 C1 C6 C5 48.1(4) . . . . ?
C2 C3 C4 F4 72.8(3) . . . . ?
C2 C3 C4 C5 -47.9(4) . . . . ?
C3 C4 C5 C6 48.0(4) . . . . ?
C4 C5 C6 F6 72.3(3) . . . . ?
C4 C5 C6 C1 -48.2(4) . . . . ?
C6 C1 C2 F2 73.5(3) . . . . ?
C6 C1 C2 C3 -48.0(4) . . . . ?
C8 O9 C10 C11 -61.3(4) . . . . ?
C8 O9 C10 C12 -179.1(3) . . . . ?
C8 O9 C10 C13 63.7(4) . . . . ?
C8 N7 C1 C2 -137.7(3) . . . . ?
C8 N7 C1 C6 93.3(3) . . . . ?
C10 O9 C8 O8 -1.0(5) . . . . ?
C10 O9 C8 N7 -179.2(3) . . . . ?
C21 N27 C28 O28 -7.9(5) . . . . ?
C21 N27 C28 O29 172.8(3) . . . . ?
C21 C22 C23 C24 49.1(4) . . . . ?
C22 C21 C26 F26 -70.7(3) . . . . ?
C22 C21 C26 C25 51.5(3) . . . . ?
C22 C23 C24 F24 75.7(3) . . . . ?
C22 C23 C24 C25 -45.2(4) . . . . ?
C23 C24 C25 C26 45.8(4) . . . . ?
C24 C25 C26 F26 72.5(3) . . . . ?
C24 C25 C26 C21 -49.2(4) . . . . ?
C26 C21 C22 F22 68.7(3) . . . . ?
C26 C21 C22 C23 -52.1(3) . . . . ?
C28 O29 C30 C31 -61.9(4) . . . . ?
C28 O29 C30 C32 178.9(3) . . . . ?
C28 O29 C30 C33 62.2(4) . . . . ?
C28 N27 C21 C22 -106.9(3) . . . . ?
C28 N27 C21 C26 124.2(3) . . . . ?
C30 O29 C28 O28 5.3(4) . . . . ?
C30 O29 C28 N27 -175.4(3) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.4988(11) 12402 712 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.5012(11) 12339 712 nmt 0.9371 0.0033 -0.0771 0.0397 1.0060 0.0790 0.7936
-0.3044 0.9704
