# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_201909246a_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2024814'
loop_
_audit_author_name
_audit_author_address
'Wenquan Yu'
;Zhengzhou University
China
;
_audit_update_record             
;
2020-08-23 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2019-09-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
6-(4-(trifluoromethyl)phenyl)benzo[4,5]imidazo[1,2-a]quinoxaline
_chemical_formula_moiety         '1(C21 H12 F3 N3)'
_chemical_formula_sum            'C21 H12 F3 N3'
_chemical_formula_weight         363.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O4N1F3
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   21.1778(12)
_cell_length_b                   7.1808(3)
_cell_length_c                   22.7192(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.911(5)
_cell_angle_gamma                90
_cell_volume                     3367.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3142
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.2330
_cell_measurement_theta_min      3.9840
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.768
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10675
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.905
_diffrn_reflns_theta_min         3.992
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00 -48.00   0.50    1.00    --  -33.50 -77.00 150.00  104
  2  ω    -69.00 -12.00   0.50    1.00    --  -33.50 -37.00-150.00  114
  3  ω    -38.00  -7.00   0.50    1.00    --  -33.50 -77.00 150.00   62
  4  ω     80.00 106.00   0.50    1.00    --   36.47  77.00  90.00   52
  5  ω      9.00  55.00   0.50    1.00    --   36.47  77.00  90.00   92
  6  ω     13.00  39.00   0.50    1.00    --   36.47  77.00 -30.00   52
  7  ω     65.00 101.00   0.50    1.00    --   36.47  77.00 -30.00   72
  8  ω     65.00 104.00   0.50    1.00    --   36.47 178.00-150.00   78
  9  ω    -22.00  47.00   0.50    1.00    --   36.47 -57.00 -60.00  138
 10  ω     60.00 110.00   0.50    1.00    --   36.47 178.00 -60.00  100
 11  ω     20.00  97.00   0.50    1.00    --   36.47  57.00  60.00  154
 12  ω    133.00 177.00   0.50   15.00    --  108.00 111.00  60.00   88
 13  ω    114.00 140.00   0.50   15.00    --  108.00 111.00-150.00   52
 14  ω     45.00 110.00   0.50   15.00    --  108.00 -94.00 150.00  130
 15  ω     84.00 113.00   0.50   15.00    --  108.00 -45.00   0.00   58
 16  ω     48.00  74.00   0.50   15.00    --  108.00 -45.00   0.00   52
 17  ω     89.00 170.00   0.50   15.00    --  108.00  61.00  90.00  162
 18  ω     39.00 127.00   0.50   15.00    --  108.00 -45.00 120.00  176
 19  ω     61.00  87.00   0.50   15.00    --  108.00-111.00 -90.00   52
 20  ω     51.00 177.00   0.50   15.00    --  108.00   0.00-120.00  252
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0577746000
_diffrn_orient_matrix_UB_12      0.0628590000
_diffrn_orient_matrix_UB_13      -0.0260139000
_diffrn_orient_matrix_UB_21      0.0442793000
_diffrn_orient_matrix_UB_22      -0.0054251000
_diffrn_orient_matrix_UB_23      0.0638055000
_diffrn_orient_matrix_UB_31      0.0164433000
_diffrn_orient_matrix_UB_32      -0.2050360000
_diffrn_orient_matrix_UB_33      -0.0097108000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6361
_reflns_number_total             10675
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         10675
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0626
_refine_ls_restrained_S_all      1.069
_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)+(0.1153P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1832
_refine_ls_wR_factor_ref         0.2029
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5444(15)
 0.4556(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 C7'-C6'
 2.1 with sigma of 0.02
 C7'-C5'
 2.2 with sigma of 0.02
 C1K-C1G
 2.2 with sigma of 0.02
 C7'A-N1'A
 1.37 with sigma of 0.02
 C7'A-N2'A
 1.37 with sigma of 0.02
 C7'-N2'
 1.37 with sigma of 0.02
 C7-N1
 1.37 with sigma of 0.02
 C7-N2
 1.37 with sigma of 0.02
 C21'-F3'A \\sim C21'-F2' \\sim C21'-F3' \\sim C21'-F2'A \\sim C21'-F1' \\sim
C21'-F1'A
 with sigma of 0.02
 F2-F3 \\sim F2-F1 \\sim F3-F1 \\sim F1A-F3A \\sim F1A-F2A \\sim F3A-F2A
 with sigma of 0.04
 C21-F2 \\sim C21-F3 \\sim C21-F1 \\sim C21-F1A \\sim C21-F3A \\sim C21-F2A
 with sigma of 0.02
4. Rigid bond restraints
 C7, N2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Uiso/Uaniso restraints and constraints
Uanis(F2') \\sim Ueq, Uanis(F2'A) \\sim Ueq, Uanis(F3') \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C7) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C8') = Uanis(C7'A)
Uanis(C7') = Uanis(N3'A)
Uanis(N3') = Uanis(N2'A)
Uanis(N2') = Uanis(C1A)
Uanis(C10') = Uanis(C9'A)
Uanis(C9') = Uanis(C1B)
Uanis(C14') = Uanis(C1C)
Uanis(C13') = Uanis(C1D)
Uanis(C12') = Uanis(C1E)
Uanis(C11') = Uanis(N1'A)
Uanis(N1') = Uanis(C6'A)
Uanis(C6') = Uanis(C5'A)
Uanis(C5') = Uanis(C4'A)
Uanis(C4') = Uanis(C3'A)
Uanis(C3') = Uanis(C2'A)
Uanis(C2') = Uanis(C1'A)
Uanis(C1') = Uanis(C1F)
Uanis(C15') = Uanis(C1G)
Uanis(C20') = Uanis(C1H)
Uanis(C19') = Uanis(C1I)
Uanis(C18') = Uanis(C1J)
Uanis(C17') = Uanis(C1K)
Uanis(F2') = Uanis(F2'A)
Uanis(F3') = Uanis(F3'A)
Uanis(F1') = Uanis(F1'A)
Uanis(F1) = Uanis(F1A)
Uanis(F3) = Uanis(F3A)
Uanis(F2) = Uanis(F2A)
6. Others
 Sof(C1B)=Sof(H1B)=Sof(C1C)=Sof(H1C)=Sof(C1D)=Sof(H1D)=Sof(C1E)=Sof(H1E)=
 Sof(C1A)=Sof(C9'A)=Sof(C1J)=Sof(H1J)=Sof(C1K)=Sof(H1K)=Sof(C1F)=Sof(C1G)=
 Sof(H1G)=Sof(C1H)=Sof(H1H)=Sof(C1I)=Sof(C6'A)=Sof(C1'A)=Sof(H1'A)=Sof(C2'A)=
 Sof(H2'A)=Sof(C3'A)=Sof(H3'A)=Sof(C4'A)=Sof(H4'A)=Sof(C5'A)=Sof(C7'A)=
 Sof(C8'A)=Sof(N1'A)=Sof(N2'A)=Sof(N3'A)=1-FVAR(1)
 Sof(C3')=Sof(H3')=Sof(C2')=Sof(H2')=Sof(C1')=Sof(H1')=Sof(C6')=Sof(C5')=
 Sof(C4')=Sof(H4')=Sof(C7')=Sof(C8')=Sof(C9')=Sof(C10')=Sof(C11')=Sof(H11')=
 Sof(C12')=Sof(H12')=Sof(C13')=Sof(H13')=Sof(C14')=Sof(H14')=Sof(C19')=
 Sof(H19')=Sof(C18')=Sof(C17')=Sof(H17')=Sof(C16')=Sof(H16')=Sof(C15')=
 Sof(C20')=Sof(H20')=Sof(N1')=Sof(N2')=Sof(N3')=FVAR(1)
 Sof(F1'A)=Sof(F2'A)=Sof(F3'A)=1-FVAR(2)
 Sof(F1')=Sof(F2')=Sof(F3')=FVAR(2)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(3)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(3)
7.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C1B(H1B), C1C(H1C), C1D(H1D), C1E(H1E),
  C1J(H1J), C1K(H1K), C1G(H1G), C1H(H1H), C3'(H3'), C2'(H2'), C1'(H1'),
 C4'(H4'), C1'A(H1'A), C2'A(H2'A), C3'A(H3'A), C4'A(H4'A), C11'(H11'),
 C12'(H12'), C13'(H13'), C14'(H14'), C19'(H19'), C17'(H17'), C16'(H16'),
 C20'(H20')
7.b Fitted hexagon refined as free rotating group:
 C1B(C1C,C1D,C1E,C1A,C9'A), C1J(C1K,C1F,C1G,C1H,C1I), C3'(C2',C1',C6',C5',C4'),
  C6'A(C1'A,C2'A,C3'A,C4'A,C5'A), C9'(C10',C11',C12',C13',C14'), C19'(C18',C17',
 C16',C15',C20')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
C1 C 0.37969(17) 0.8324(5) 0.32218(16) 0.0771(9) Uani 1 1 d . . . . .
H1 H 0.3723 0.8147 0.2806 0.092 Uiso 1 1 calc R . . . .
C2 C 0.33145(18) 0.8939(5) 0.34914(18) 0.0866(10) Uani 1 1 d . . . . .
H2 H 0.2906 0.9174 0.3251 0.104 Uiso 1 1 calc R . . . .
C3 C 0.34182(18) 0.9220(5) 0.41074(18) 0.0839(10) Uani 1 1 d . . . . .
H3 H 0.3082 0.9676 0.4268 0.101 Uiso 1 1 calc R . . . .
C4 C 0.40060(16) 0.8841(5) 0.44882(16) 0.0744(8) Uani 1 1 d . . . . .
H4 H 0.4069 0.9013 0.4903 0.089 Uiso 1 1 calc R . . . .
C5 C 0.45071(15) 0.8187(4) 0.42307(13) 0.0632(7) Uani 1 1 d . . . . .
C6 C 0.44032(15) 0.7976(4) 0.35991(13) 0.0609(7) Uani 1 1 d . . . . .
C7 C 0.54071(14) 0.7324(4) 0.40734(13) 0.0606(6) Uani 1 1 d D U . . .
C8 C 0.60703(14) 0.6838(4) 0.41072(13) 0.0616(7) Uani 1 1 d . . . . .
C9 C 0.58879(14) 0.6776(4) 0.30543(13) 0.0606(7) Uani 1 1 d . . . . .
C10 C 0.52263(15) 0.7162(4) 0.29696(13) 0.0601(7) Uani 1 1 d . . . . .
C11 C 0.48340(17) 0.7279(5) 0.23912(14) 0.0728(8) Uani 1 1 d . . . . .
H11 H 0.4394 0.7532 0.2335 0.087 Uiso 1 1 calc R . . . .
C12 C 0.51097(19) 0.7014(5) 0.19051(15) 0.0854(10) Uani 1 1 d . . . . .
H12 H 0.4850 0.7085 0.1517 0.103 Uiso 1 1 calc R . . . .
C13 C 0.5762(2) 0.6647(5) 0.19770(16) 0.0834(10) Uani 1 1 d . . . . .
H13 H 0.5937 0.6472 0.1641 0.100 Uiso 1 1 calc R . . . .
C14 C 0.61496(18) 0.6540(5) 0.25465(15) 0.0757(9) Uani 1 1 d . . . . .
H14 H 0.6590 0.6310 0.2595 0.091 Uiso 1 1 calc R . . . .
C15 C 0.65214(15) 0.6634(4) 0.47133(13) 0.0637(7) Uani 1 1 d . . . . .
C16 C 0.71621(16) 0.7135(4) 0.47655(15) 0.0729(8) Uani 1 1 d . . . . .
H16 H 0.7292 0.7627 0.4433 0.087 Uiso 1 1 calc R . . . .
C17 C 0.76061(17) 0.6918(5) 0.52969(17) 0.0817(9) Uani 1 1 d . . . . .
H17 H 0.8033 0.7288 0.5327 0.098 Uiso 1 1 calc R . . . .
C18 C 0.74238(17) 0.6154(5) 0.57881(15) 0.0775(9) Uani 1 1 d . . . . .
C19 C 0.67895(18) 0.5589(5) 0.57422(14) 0.0755(8) Uani 1 1 d . . . . .
H19 H 0.6667 0.5043 0.6071 0.091 Uiso 1 1 calc R . . . .
C20 C 0.63390(16) 0.5843(4) 0.52025(15) 0.0708(8) Uani 1 1 d . . . . .
H20 H 0.5911 0.5477 0.5171 0.085 Uiso 1 1 calc R . . . .
C21 C 0.7898(3) 0.5957(8) 0.6367(2) 0.1204(18) Uani 1 1 d D . . . .
F1 F 0.7736(4) 0.4929(14) 0.6780(3) 0.218(5) Uani 0.649(5) 1 d D . P A 1
F1A F 0.7630(7) 0.638(2) 0.6816(5) 0.218(5) Uani 0.351(5) 1 d D . P A 2
F2 F 0.8045(4) 0.7607(9) 0.6655(3) 0.167(3) Uani 0.649(5) 1 d D . P A 1
F2A F 0.8396(7) 0.6934(19) 0.6436(5) 0.167(3) Uani 0.351(5) 1 d D . P A 2
F3 F 0.8500(3) 0.5504(13) 0.6313(3) 0.179(3) Uani 0.649(5) 1 d D . P A 1
F3A F 0.8073(6) 0.4134(19) 0.6434(6) 0.179(3) Uani 0.351(5) 1 d D . P A 2
N1 N 0.49996(12) 0.7429(3) 0.34943(10) 0.0585(6) Uani 1 1 d D . . . .
N2 N 0.51287(12) 0.7742(3) 0.45254(11) 0.0646(6) Uani 1 1 d D U . . .
N3 N 0.62963(12) 0.6619(3) 0.36200(11) 0.0625(6) Uani 1 1 d . . . . .
C1B C 0.6918(4) 0.0442(16) 0.1635(4) 0.0689(15) Uani 0.443(5) 1 d . . P B 2
H1B H 0.7360 0.0207 0.1700 0.083 Uiso 0.443(5) 1 calc R . P B 2
C1C C 0.6529(5) 0.0313(16) 0.1057(4) 0.0731(16) Uani 0.443(5) 1 d G . P B 2
H1C H 0.6711 -0.0008 0.0734 0.088 Uiso 0.443(5) 1 calc R . P B 2
C1D C 0.5869(5) 0.0665(16) 0.0960(4) 0.0810(18) Uani 0.443(5) 1 d G . P B 2
H1D H 0.5609 0.0578 0.0573 0.097 Uiso 0.443(5) 1 calc R . P B 2
C1E C 0.5597(4) 0.1145(16) 0.1442(5) 0.091(2) Uani 0.443(5) 1 d G . P B 2
H1E H 0.5155 0.1381 0.1377 0.109 Uiso 0.443(5) 1 calc R . P B 2
C1A C 0.5986(5) 0.1274(16) 0.2021(5) 0.0588(16) Uani 0.443(5) 1 d G . P B 2
C9'A C 0.6646(5) 0.0922(16) 0.2118(4) 0.0727(19) Uani 0.443(5) 1 d G . P B 2
C1J C 0.8460(4) 0.040(2) 0.4357(5) 0.0763(17) Uani 0.443(5) 1 d . . P B 2
H1J H 0.8856 -0.0175 0.4372 0.092 Uiso 0.443(5) 1 calc R . P B 2
C1K C 0.7982(4) 0.0361(15) 0.3827(4) 0.0720(16) Uani 0.443(5) 1 d DG . P B 2
H1K H 0.8058 -0.0243 0.3487 0.086 Uiso 0.443(5) 1 calc R . P B 2
C1F C 0.7389(4) 0.1223(12) 0.3804(3) 0.0721(16) Uani 0.443(5) 1 d G . P B 2
C1G C 0.7274(4) 0.2125(11) 0.4311(3) 0.0657(14) Uani 0.443(5) 1 d DG . P B 2
H1G H 0.6878 0.2702 0.4296 0.079 Uiso 0.443(5) 1 calc R . P B 2
C1H C 0.7752(5) 0.2166(14) 0.4841(3) 0.0784(17) Uani 0.443(5) 1 d G . P B 2
H1H H 0.7676 0.2770 0.5181 0.094 Uiso 0.443(5) 1 calc R . P B 2
C1I C 0.8345(5) 0.130(2) 0.4864(4) 0.0786(17) Uani 0.443(5) 1 d G . P B 2
C3' C 0.6465(5) 0.0652(13) 0.0958(3) 0.095(2) Uani 0.557(5) 1 d . . P B 1
H3' H 0.6605 0.0383 0.0608 0.114 Uiso 0.557(5) 1 calc R . P B 1
C2' C 0.5817(4) 0.1072(12) 0.0925(3) 0.091(2) Uani 0.557(5) 1 d G . P B 1
H2' H 0.5524 0.1084 0.0553 0.109 Uiso 0.557(5) 1 calc R . P B 1
C1' C 0.5607(3) 0.1474(11) 0.1449(4) 0.0721(16) Uani 0.557(5) 1 d G . P B 1
H1' H 0.5174 0.1755 0.1427 0.087 Uiso 0.557(5) 1 calc R . P B 1
C6' C 0.6044(4) 0.1456(12) 0.2005(4) 0.0757(19) Uani 0.557(5) 1 d DG . P B 1
C5' C 0.6692(4) 0.1036(14) 0.2038(3) 0.0741(18) Uani 0.557(5) 1 d DG . P B 1
C4' C 0.6902(4) 0.0634(14) 0.1514(4) 0.087(2) Uani 0.557(5) 1 d G . P B 1
H4' H 0.7336 0.0353 0.1536 0.104 Uiso 0.557(5) 1 calc R . P B 1
C6'A C 0.5241(5) 0.212(2) 0.2724(5) 0.0718(19) Uani 0.443(5) 1 d . . P B 2
C1'A C 0.4643(6) 0.247(2) 0.2341(3) 0.091(2) Uani 0.443(5) 1 d G . P B 2
H1'A H 0.4598 0.2404 0.1925 0.109 Uiso 0.443(5) 1 calc R . P B 2
C2'A C 0.4112(5) 0.2916(19) 0.2580(4) 0.095(2) Uani 0.443(5) 1 d G . P B 2
H2'A H 0.3712 0.3147 0.2323 0.114 Uiso 0.443(5) 1 calc R . P B 2
C3'A C 0.4180(4) 0.3016(15) 0.3202(4) 0.087(2) Uani 0.443(5) 1 d G . P B 2
H3'A H 0.3824 0.3314 0.3361 0.104 Uiso 0.443(5) 1 calc R . P B 2
C4'A C 0.4778(4) 0.2670(12) 0.3585(3) 0.0741(18) Uani 0.443(5) 1 d G . P B 2
H4'A H 0.4823 0.2736 0.4001 0.089 Uiso 0.443(5) 1 calc R . P B 2
C5'A C 0.5309(3) 0.2224(15) 0.3346(4) 0.0757(19) Uani 0.443(5) 1 d G . P B 2
C7' C 0.6549(3) 0.1431(7) 0.2912(3) 0.0613(13) Uani 0.557(5) 1 d D . P B 1
C7'A C 0.6222(4) 0.1630(8) 0.3180(3) 0.0588(9) Uani 0.443(5) 1 d D . P B 2
C8' C 0.6613(3) 0.1590(6) 0.3553(3) 0.0588(9) Uani 0.557(5) 1 d . . P B 1
C8'A C 0.6899(4) 0.1258(9) 0.3216(4) 0.0612(18) Uani 0.443(5) 1 d . . P B 2
C9' C 0.5490(2) 0.2138(12) 0.3408(3) 0.0689(15) Uani 0.557(5) 1 d . . P B 1
C10' C 0.5364(3) 0.2049(15) 0.2781(3) 0.0727(19) Uani 0.557(5) 1 d G . P B 1
C11' C 0.4737(4) 0.2307(16) 0.2444(2) 0.084(2) Uani 0.557(5) 1 d G . P B 1
H11' H 0.4653 0.2247 0.2024 0.101 Uiso 0.557(5) 1 calc R . P B 1
C12' C 0.4236(3) 0.2655(14) 0.2732(3) 0.091(2) Uani 0.557(5) 1 d G . P B 1
H12' H 0.3816 0.2828 0.2506 0.109 Uiso 0.557(5) 1 calc R . P B 1
C13' C 0.4361(2) 0.2744(11) 0.3359(3) 0.0810(18) Uani 0.557(5) 1 d G . P B 1
H13' H 0.4026 0.2976 0.3552 0.097 Uiso 0.557(5) 1 calc R . P B 1
C14' C 0.4988(3) 0.2485(10) 0.3697(2) 0.0731(16) Uani 0.557(5) 1 d G . P B 1
H14' H 0.5073 0.2545 0.4116 0.088 Uiso 0.557(5) 1 calc R . P B 1
C19' C 0.7882(4) 0.1892(12) 0.4990(2) 0.0786(17) Uani 0.557(5) 1 d . . P B 1
H19' H 0.7919 0.2355 0.5379 0.094 Uiso 0.557(5) 1 calc R . P B 1
C18' C 0.8405(3) 0.1004(15) 0.4836(3) 0.0763(17) Uani 0.557(5) 1 d G . P B 1
C17' C 0.8350(3) 0.0312(15) 0.4255(3) 0.0720(16) Uani 0.557(5) 1 d G . P B 1
H17' H 0.8700 -0.0282 0.4152 0.086 Uiso 0.557(5) 1 calc R . P B 1
C16' C 0.7771(3) 0.0508(10) 0.3829(2) 0.0643(16) Uani 0.557(5) 1 d G . P B 1
H16' H 0.7733 0.0045 0.3440 0.077 Uiso 0.557(5) 1 calc R . P B 1
C15' C 0.7247(2) 0.1396(8) 0.3983(2) 0.0657(14) Uani 0.557(5) 1 d G . P B 1
C20' C 0.7303(3) 0.2088(9) 0.4564(2) 0.0784(17) Uani 0.557(5) 1 d G . P B 1
H20' H 0.6952 0.2682 0.4667 0.094 Uiso 0.557(5) 1 calc R . P B 1
C21' C 0.8963(4) 0.1036(11) 0.5342(3) 0.146(3) Uani 1 1 d D . . . .
F1' F 0.8803(4) 0.1188(13) 0.5892(2) 0.198(3) Uani 0.693(7) 1 d D . P B 1
F1'A F 0.9045(10) 0.291(2) 0.5584(6) 0.198(3) Uani 0.307(7) 1 d D . P B 2
F2' F 0.9387(4) 0.2302(16) 0.5312(4) 0.252(5) Uani 0.693(7) 1 d D U P B 1
F2'A F 0.9475(9) 0.100(4) 0.5129(10) 0.252(5) Uani 0.307(7) 1 d D U P B 2
F3' F 0.9281(3) -0.0560(11) 0.5380(3) 0.183(3) Uani 0.693(7) 1 d D U P B 1
F3'A F 0.8964(8) 0.013(3) 0.5794(8) 0.183(3) Uani 0.307(7) 1 d D . P B 2
N1' N 0.7027(7) 0.1169(12) 0.2616(5) 0.0718(19) Uani 0.557(5) 1 d . . P B 1
N1'A N 0.5924(7) 0.196(2) 0.3620(6) 0.084(2) Uani 0.443(5) 1 d D . P B 2
N2' N 0.5932(3) 0.1646(12) 0.2530(4) 0.0588(16) Uani 0.557(5) 1 d D . P B 1
N2'A N 0.5788(5) 0.1737(17) 0.2610(5) 0.0612(15) Uani 0.443(5) 1 d D . P B 2
N3' N 0.6094(4) 0.1875(12) 0.3774(3) 0.0612(15) Uani 0.557(5) 1 d . . P B 1
N3'A N 0.7062(7) 0.0820(16) 0.2701(7) 0.0613(13) Uani 0.443(5) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1 H1 0.9300 . ?
C1 C2 1.376(5) . ?
C1 C6 1.398(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.402(4) . ?
C5 C6 1.410(4) . ?
C5 N2 1.375(4) . ?
C6 N1 1.393(4) . ?
C7 C8 1.432(4) . ?
C7 N1 1.405(3) . ?
C7 N2 1.328(4) . ?
C8 C15 1.498(4) . ?
C8 N3 1.310(4) . ?
C9 C10 1.399(4) . ?
C9 C14 1.397(4) . ?
C9 N3 1.384(4) . ?
C10 C11 1.392(4) . ?
C10 N1 1.394(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.371(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(5) . ?
C15 C20 1.378(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.363(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(5) . ?
C18 C19 1.385(5) . ?
C18 C21 1.473(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.387(4) . ?
C20 H20 0.9300 . ?
C21 F1 1.299(8) . ?
C21 F1A 1.309(14) . ?
C21 F2 1.356(8) . ?
C21 F2A 1.246(12) . ?
C21 F3 1.346(8) . ?
C21 F3A 1.360(12) . ?
C1B H1B 0.9300 . ?
C1B C1C 1.3900 . ?
C1B C9'A 1.3900 . ?
C1C H1C 0.9300 . ?
C1C C1D 1.3900 . ?
C1D H1D 0.9300 . ?
C1D C1E 1.3900 . ?
C1E H1E 0.9300 . ?
C1E C1A 1.3900 . ?
C1A C9'A 1.3900 . ?
C1A N2'A 1.525(13) . ?
C9'A N3'A 1.420(17) . ?
C1J H1J 0.9300 . ?
C1J C1K 1.3900 . ?
C1J C1I 1.3900 . ?
C1K H1K 0.9300 . ?
C1K C1F 1.3900 . ?
C1F C1G 1.3900 . ?
C1F C8'A 1.496(10) . ?
C1G H1G 0.9300 . ?
C1G C1H 1.3900 . ?
C1H H1H 0.9300 . ?
C1H C1I 1.3900 . ?
C1I C21' 1.514(9) . ?
C3' H3' 0.9300 . ?
C3' C2' 1.3900 . ?
C3' C4' 1.3900 . ?
C2' H2' 0.9300 . ?
C2' C1' 1.3900 . ?
C1' H1' 0.9300 . ?
C1' C6' 1.3900 . ?
C6' C5' 1.3900 . ?
C6' N2' 1.275(10) . ?
C5' C4' 1.3900 . ?
C5' N1' 1.349(15) . ?
C4' H4' 0.9300 . ?
C6'A C1'A 1.3900 . ?
C6'A C5'A 1.3900 . ?
C6'A N2'A 1.274(12) . ?
C1'A H1'A 0.9300 . ?
C1'A C2'A 1.3900 . ?
C2'A H2'A 0.9300 . ?
C2'A C3'A 1.3900 . ?
C3'A H3'A 0.9300 . ?
C3'A C4'A 1.3900 . ?
C4'A H4'A 0.9300 . ?
C4'A C5'A 1.3900 . ?
C5'A N1'A 1.327(14) . ?
C7' C8' 1.436(9) . ?
C7' N1' 1.349(13) . ?
C7' N2' 1.405(10) . ?
C7'A C8'A 1.443(11) . ?
C7'A N1'A 1.316(14) . ?
C7'A N2'A 1.413(13) . ?
C8' C15' 1.480(7) . ?
C8' N3' 1.322(11) . ?
C8'A N3'A 1.329(16) . ?
C9' C10' 1.3900 . ?
C9' C14' 1.3900 . ?
C9' N3' 1.374(8) . ?
C10' C11' 1.3900 . ?
C10' N2' 1.471(8) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.3900 . ?
C12' H12' 0.9300 . ?
C12' C13' 1.3900 . ?
C13' H13' 0.9300 . ?
C13' C14' 1.3900 . ?
C14' H14' 0.9300 . ?
C19' H19' 0.9300 . ?
C19' C18' 1.3900 . ?
C19' C20' 1.3900 . ?
C18' C17' 1.3900 . ?
C18' C21' 1.452(7) . ?
C17' H17' 0.9300 . ?
C17' C16' 1.3900 . ?
C16' H16' 0.9300 . ?
C16' C15' 1.3900 . ?
C15' C20' 1.3900 . ?
C20' H20' 0.9300 . ?
C21' F1' 1.371(9) . ?
C21' F1'A 1.452(15) . ?
C21' F2' 1.290(9) . ?
C21' F2'A 1.282(17) . ?
C21' F3' 1.322(9) . ?
C21' F3'A 1.217(15) . ?

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
C2 C1 H1 121.4 . . ?
C2 C1 C6 117.1(3) . . ?
C6 C1 H1 121.4 . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.1(3) . . ?
C3 C2 H2 118.9 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.7(4) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.8(3) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 C6 120.0(3) . . ?
N2 C5 C4 127.3(3) . . ?
N2 C5 C6 112.7(3) . . ?
C1 C6 C5 121.2(3) . . ?
N1 C6 C1 133.6(3) . . ?
N1 C6 C5 105.2(2) . . ?
N1 C7 C8 116.9(3) . . ?
N2 C7 C8 127.8(3) . . ?
N2 C7 N1 115.2(3) . . ?
C7 C8 C15 119.3(3) . . ?
N3 C8 C7 121.5(3) . . ?
N3 C8 C15 119.1(3) . . ?
C14 C9 C10 118.7(3) . . ?
N3 C9 C10 122.9(3) . . ?
N3 C9 C14 118.4(3) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 N1 123.5(3) . . ?
N1 C10 C9 115.8(3) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 C10 118.7(3) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.7(3) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.5(4) . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C8 117.7(3) . . ?
C20 C15 C8 123.1(3) . . ?
C20 C15 C16 119.0(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.1(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 C21 120.3(4) . . ?
C19 C18 C21 119.7(4) . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.5(3) . . ?
C20 C19 H19 120.3 . . ?
C15 C20 C19 120.4(3) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
F1 C21 C18 117.5(5) . . ?
F1 C21 F2 102.5(7) . . ?
F1 C21 F3 109.7(7) . . ?
F1A C21 C18 110.2(7) . . ?
F1A C21 F3A 106.9(10) . . ?
F2 C21 C18 112.6(5) . . ?
F2A C21 C18 116.6(7) . . ?
F2A C21 F1A 105.9(10) . . ?
F2A C21 F3A 109.1(9) . . ?
F3 C21 C18 114.3(5) . . ?
F3 C21 F2 97.8(6) . . ?
F3A C21 C18 107.9(6) . . ?
C6 N1 C7 104.2(2) . . ?
C6 N1 C10 133.1(2) . . ?
C10 N1 C7 122.4(3) . . ?
C7 N2 C5 102.6(2) . . ?
C8 N3 C9 120.3(3) . . ?
C1C C1B H1B 120.0 . . ?
C1C C1B C9'A 120.0 . . ?
C9'A C1B H1B 120.0 . . ?
C1B C1C H1C 120.0 . . ?
C1D C1C C1B 120.0 . . ?
C1D C1C H1C 120.0 . . ?
C1C C1D H1D 120.0 . . ?
C1C C1D C1E 120.0 . . ?
C1E C1D H1D 120.0 . . ?
C1D C1E H1E 120.0 . . ?
C1A C1E C1D 120.0 . . ?
C1A C1E H1E 120.0 . . ?
C1E C1A C9'A 120.0 . . ?
C1E C1A N2'A 128.6(7) . . ?
C9'A C1A N2'A 111.4(7) . . ?
C1B C9'A N3'A 116.4(8) . . ?
C1A C9'A C1B 120.0 . . ?
C1A C9'A N3'A 123.3(8) . . ?
C1K C1J H1J 120.0 . . ?
C1K C1J C1I 120.0 . . ?
C1I C1J H1J 120.0 . . ?
C1J C1K H1K 120.0 . . ?
C1F C1K C1J 120.0 . . ?
C1F C1K H1K 120.0 . . ?
C1K C1F C8'A 118.8(6) . . ?
C1G C1F C1K 120.0 . . ?
C1G C1F C8'A 121.1(6) . . ?
C1F C1G H1G 120.0 . . ?
C1F C1G C1H 120.0 . . ?
C1H C1G H1G 120.0 . . ?
C1G C1H H1H 120.0 . . ?
C1I C1H C1G 120.0 . . ?
C1I C1H H1H 120.0 . . ?
C1J C1I C21' 104.6(7) . . ?
C1H C1I C1J 120.0 . . ?
C1H C1I C21' 135.4(7) . . ?
C2' C3' H3' 120.0 . . ?
C2' C3' C4' 120.0 . . ?
C4' C3' H3' 120.0 . . ?
C3' C2' H2' 120.0 . . ?
C1' C2' C3' 120.0 . . ?
C1' C2' H2' 120.0 . . ?
C2' C1' H1' 120.0 . . ?
C2' C1' C6' 120.0 . . ?
C6' C1' H1' 120.0 . . ?
C5' C6' C1' 120.0 . . ?
N2' C6' C1' 128.6(7) . . ?
N2' C6' C5' 111.1(7) . . ?
C6' C5' C4' 120.0 . . ?
N1' C5' C6' 109.6(8) . . ?
N1' C5' C4' 130.4(8) . . ?
C3' C4' H4' 120.0 . . ?
C5' C4' C3' 120.0 . . ?
C5' C4' H4' 120.0 . . ?
C1'A C6'A C5'A 120.0 . . ?
N2'A C6'A C1'A 130.9(9) . . ?
N2'A C6'A C5'A 109.1(9) . . ?
C6'A C1'A H1'A 120.0 . . ?
C2'A C1'A C6'A 120.0 . . ?
C2'A C1'A H1'A 120.0 . . ?
C1'A C2'A H2'A 120.0 . . ?
C3'A C2'A C1'A 120.0 . . ?
C3'A C2'A H2'A 120.0 . . ?
C2'A C3'A H3'A 120.0 . . ?
C4'A C3'A C2'A 120.0 . . ?
C4'A C3'A H3'A 120.0 . . ?
C3'A C4'A H4'A 120.0 . . ?
C3'A C4'A C5'A 120.0 . . ?
C5'A C4'A H4'A 120.0 . . ?
C4'A C5'A C6'A 120.0 . . ?
N1'A C5'A C6'A 109.6(9) . . ?
N1'A C5'A C4'A 130.3(9) . . ?
N1' C7' C8' 127.3(7) . . ?
N1' C7' N2' 113.9(7) . . ?
N2' C7' C8' 118.8(6) . . ?
N1'A C7'A C8'A 128.9(8) . . ?
N1'A C7'A N2'A 111.3(9) . . ?
N2'A C7'A C8'A 119.8(7) . . ?
C7' C8' C15' 121.9(5) . . ?
N3' C8' C7' 120.0(6) . . ?
N3' C8' C15' 118.2(5) . . ?
C7'A C8'A C1F 122.4(7) . . ?
N3'A C8'A C1F 121.1(10) . . ?
N3'A C8'A C7'A 116.3(10) . . ?
C10' C9' C14' 120.0 . . ?
N3' C9' C10' 123.6(6) . . ?
N3' C9' C14' 116.4(6) . . ?
C9' C10' C11' 120.0 . . ?
C9' C10' N2' 114.8(6) . . ?
C11' C10' N2' 125.2(6) . . ?
C10' C11' H11' 120.0 . . ?
C12' C11' C10' 120.0 . . ?
C12' C11' H11' 120.0 . . ?
C11' C12' H12' 120.0 . . ?
C11' C12' C13' 120.0 . . ?
C13' C12' H12' 120.0 . . ?
C12' C13' H13' 120.0 . . ?
C14' C13' C12' 120.0 . . ?
C14' C13' H13' 120.0 . . ?
C9' C14' H14' 120.0 . . ?
C13' C14' C9' 120.0 . . ?
C13' C14' H14' 120.0 . . ?
C18' C19' H19' 120.0 . . ?
C18' C19' C20' 120.0 . . ?
C20' C19' H19' 120.0 . . ?
C19' C18' C21' 110.3(6) . . ?
C17' C18' C19' 120.0 . . ?
C17' C18' C21' 129.7(6) . . ?
C18' C17' H17' 120.0 . . ?
C18' C17' C16' 120.0 . . ?
C16' C17' H17' 120.0 . . ?
C17' C16' H16' 120.0 . . ?
C15' C16' C17' 120.0 . . ?
C15' C16' H16' 120.0 . . ?
C16' C15' C8' 122.3(4) . . ?
C16' C15' C20' 120.0 . . ?
C20' C15' C8' 117.7(4) . . ?
C19' C20' H20' 120.0 . . ?
C15' C20' C19' 120.0 . . ?
C15' C20' H20' 120.0 . . ?
F1' C21' C18' 113.6(8) . . ?
F1'A C21' C1I 99.5(10) . . ?
F2' C21' C18' 115.0(8) . . ?
F2' C21' F1' 107.9(8) . . ?
F2' C21' F3' 105.3(10) . . ?
F2'A C21' C1I 113.7(12) . . ?
F2'A C21' F1'A 96.9(13) . . ?
F3' C21' C18' 110.5(6) . . ?
F3' C21' F1' 103.6(7) . . ?
F3'A C21' C1I 120.7(11) . . ?
F3'A C21' F1'A 101.5(13) . . ?
F3'A C21' F2'A 117.8(16) . . ?
C7' N1' C5' 101.8(10) . . ?
C7'A N1'A C5'A 104.9(10) . . ?
C6' N2' C7' 103.0(6) . . ?
C6' N2' C10' 136.3(8) . . ?
C7' N2' C10' 120.7(7) . . ?
C6'A N2'A C1A 131.9(10) . . ?
C6'A N2'A C7'A 105.0(10) . . ?
C7'A N2'A C1A 122.9(9) . . ?
C8' N3' C9' 122.1(6) . . ?
C8'A N3'A C9'A 125.6(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
C1 C2 C3 C4 -2.1(6) . . . . ?
C1 C6 N1 C7 -179.7(3) . . . . ?
C1 C6 N1 C10 5.8(5) . . . . ?
C2 C1 C6 C5 2.1(5) . . . . ?
C2 C1 C6 N1 -177.0(3) . . . . ?
C2 C3 C4 C5 1.2(6) . . . . ?
C3 C4 C5 C6 1.4(5) . . . . ?
C3 C4 C5 N2 179.4(3) . . . . ?
C4 C5 C6 C1 -3.1(5) . . . . ?
C4 C5 C6 N1 176.3(3) . . . . ?
C4 C5 N2 C7 -176.1(3) . . . . ?
C5 C6 N1 C7 1.1(3) . . . . ?
C5 C6 N1 C10 -173.4(3) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
C6 C5 N2 C7 2.0(3) . . . . ?
C7 C8 C15 C16 -146.7(3) . . . . ?
C7 C8 C15 C20 38.5(4) . . . . ?
C7 C8 N3 C9 -2.8(4) . . . . ?
C8 C7 N1 C6 -178.1(2) . . . . ?
C8 C7 N1 C10 -2.8(4) . . . . ?
C8 C7 N2 C5 176.7(3) . . . . ?
C8 C15 C16 C17 -177.4(3) . . . . ?
C8 C15 C20 C19 176.0(3) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C9 C10 N1 C6 173.9(3) . . . . ?
C9 C10 N1 C7 0.1(4) . . . . ?
C10 C9 C14 C13 -1.4(5) . . . . ?
C10 C9 N3 C8 -0.1(4) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C11 C10 N1 C6 -5.5(5) . . . . ?
C11 C10 N1 C7 -179.3(3) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C12 C13 C14 C9 0.9(5) . . . . ?
C14 C9 C10 C11 1.1(4) . . . . ?
C14 C9 C10 N1 -178.4(3) . . . . ?
C14 C9 N3 C8 179.7(3) . . . . ?
C15 C8 N3 C9 179.1(2) . . . . ?
C15 C16 C17 C18 1.5(6) . . . . ?
C16 C15 C20 C19 1.3(5) . . . . ?
C16 C17 C18 C19 0.5(6) . . . . ?
C16 C17 C18 C21 -178.6(4) . . . . ?
C17 C18 C19 C20 -1.6(5) . . . . ?
C17 C18 C21 F1 -167.7(8) . . . . ?
C17 C18 C21 F1A 139.5(9) . . . . ?
C17 C18 C21 F2 73.5(8) . . . . ?
C17 C18 C21 F2A 18.8(11) . . . . ?
C17 C18 C21 F3 -37.0(8) . . . . ?
C17 C18 C21 F3A -104.2(9) . . . . ?
C18 C19 C20 C15 0.6(5) . . . . ?
C19 C18 C21 F1 13.2(10) . . . . ?
C19 C18 C21 F1A -39.6(10) . . . . ?
C19 C18 C21 F2 -105.6(7) . . . . ?
C19 C18 C21 F2A -160.3(9) . . . . ?
C19 C18 C21 F3 143.9(6) . . . . ?
C19 C18 C21 F3A 76.7(10) . . . . ?
C20 C15 C16 C17 -2.4(5) . . . . ?
C21 C18 C19 C20 177.6(4) . . . . ?
N1 C7 C8 C15 -177.7(2) . . . . ?
N1 C7 C8 N3 4.2(4) . . . . ?
N1 C7 N2 C5 -1.3(3) . . . . ?
N1 C10 C11 C12 179.2(3) . . . . ?
N2 C5 C6 C1 178.6(3) . . . . ?
N2 C5 C6 N1 -2.0(3) . . . . ?
N2 C7 C8 C15 4.3(4) . . . . ?
N2 C7 C8 N3 -173.7(3) . . . . ?
N2 C7 N1 C6 0.1(3) . . . . ?
N2 C7 N1 C10 175.4(2) . . . . ?
N3 C8 C15 C16 31.4(4) . . . . ?
N3 C8 C15 C20 -143.4(3) . . . . ?
N3 C9 C10 C11 -179.1(3) . . . . ?
N3 C9 C10 N1 1.5(4) . . . . ?
N3 C9 C14 C13 178.7(3) . . . . ?
C1B C1C C1D C1E 0.0 . . . . ?
C1B C9'A N3'A C8'A 178.5(9) . . . . ?
C1C C1B C9'A C1A 0.0 . . . . ?
C1C C1B C9'A N3'A 173.2(11) . . . . ?
C1C C1D C1E C1A 0.0 . . . . ?
C1D C1E C1A C9'A 0.0 . . . . ?
C1D C1E C1A N2'A -178.7(11) . . . . ?
C1E C1A C9'A C1B 0.0 . . . . ?
C1E C1A C9'A N3'A -172.7(12) . . . . ?
C1E C1A N2'A C6'A -1(2) . . . . ?
C1E C1A N2'A C7'A 173.0(8) . . . . ?
C1A C9'A N3'A C8'A -8.6(17) . . . . ?
C9'A C1B C1C C1D 0.0 . . . . ?
C9'A C1A N2'A C6'A -179.3(14) . . . . ?
C9'A C1A N2'A C7'A -5.7(13) . . . . ?
C1J C1K C1F C1G 0.0 . . . . ?
C1J C1K C1F C8'A 176.3(7) . . . . ?
C1J C1I C21' F1'A 135.2(10) . . . . ?
C1J C1I C21' F2'A 33.3(15) . . . . ?
C1J C1I C21' F3'A -115.2(16) . . . . ?
C1K C1J C1I C1H 0.0 . . . . ?
C1K C1J C1I C21' 179.5(11) . . . . ?
C1K C1F C1G C1H 0.0 . . . . ?
C1K C1F C8'A C7'A 162.1(6) . . . . ?
C1K C1F C8'A N3'A -13.3(10) . . . . ?
C1F C1G C1H C1I 0.0 . . . . ?
C1F C8'A N3'A C9'A -175.8(10) . . . . ?
C1G C1F C8'A C7'A -21.7(9) . . . . ?
C1G C1F C8'A N3'A 162.9(8) . . . . ?
C1G C1H C1I C1J 0.0 . . . . ?
C1G C1H C1I C21' -179.3(15) . . . . ?
C1H C1I C21' F1'A -45.4(16) . . . . ?
C1H C1I C21' F2'A -147.3(16) . . . . ?
C1H C1I C21' F3'A 64(2) . . . . ?
C1I C1J C1K C1F 0.0 . . . . ?
C3' C2' C1' C6' 0.0 . . . . ?
C2' C3' C4' C5' 0.0 . . . . ?
C2' C1' C6' C5' 0.0 . . . . ?
C2' C1' C6' N2' -174.1(10) . . . . ?
C1' C6' C5' C4' 0.0 . . . . ?
C1' C6' C5' N1' 177.8(9) . . . . ?
C1' C6' N2' C7' 177.7(6) . . . . ?
C1' C6' N2' C10' -4.4(16) . . . . ?
C6' C5' C4' C3' 0.0 . . . . ?
C6' C5' N1' C7' 7.5(8) . . . . ?
C5' C6' N2' C7' 3.1(8) . . . . ?
C5' C6' N2' C10' -178.9(10) . . . . ?
C4' C3' C2' C1' 0.0 . . . . ?
C4' C5' N1' C7' -175.1(6) . . . . ?
C6'A C1'A C2'A C3'A 0.0 . . . . ?
C6'A C5'A N1'A C7'A -2.4(13) . . . . ?
C1'A C6'A C5'A C4'A 0.0 . . . . ?
C1'A C6'A C5'A N1'A -176.2(11) . . . . ?
C1'A C6'A N2'A C1A -9(2) . . . . ?
C1'A C6'A N2'A C7'A 177.1(8) . . . . ?
C1'A C2'A C3'A C4'A 0.0 . . . . ?
C2'A C3'A C4'A C5'A 0.0 . . . . ?
C3'A C4'A C5'A C6'A 0.0 . . . . ?
C3'A C4'A C5'A N1'A 175.3(14) . . . . ?
C4'A C5'A N1'A C7'A -178.1(9) . . . . ?
C5'A C6'A C1'A C2'A 0.0 . . . . ?
C5'A C6'A N2'A C1A 173.0(12) . . . . ?
C5'A C6'A N2'A C7'A -1.4(12) . . . . ?
C7' C8' C15' C16' -20.2(7) . . . . ?
C7' C8' C15' C20' 161.7(4) . . . . ?
C7' C8' N3' C9' -3.9(11) . . . . ?
C7'A C8'A N3'A C9'A 8.6(15) . . . . ?
C8' C7' N1' C5' 177.2(6) . . . . ?
C8' C7' N2' C6' 179.1(6) . . . . ?
C8' C7' N2' C10' 0.7(11) . . . . ?
C8' C15' C20' C19' 178.1(5) . . . . ?
C8'A C1F C1G C1H -176.2(8) . . . . ?
C8'A C7'A N1'A C5'A 179.6(8) . . . . ?
C8'A C7'A N2'A C1A 6.7(14) . . . . ?
C8'A C7'A N2'A C6'A -178.3(9) . . . . ?
C9' C10' C11' C12' 0.0 . . . . ?
C9' C10' N2' C6' -179.4(10) . . . . ?
C9' C10' N2' C7' -1.7(11) . . . . ?
C10' C9' C14' C13' 0.0 . . . . ?
C10' C9' N3' C8' 2.9(12) . . . . ?
C10' C11' C12' C13' 0.0 . . . . ?
C11' C10' N2' C6' 1.5(16) . . . . ?
C11' C10' N2' C7' 179.2(6) . . . . ?
C11' C12' C13' C14' 0.0 . . . . ?
C12' C13' C14' C9' 0.0 . . . . ?
C14' C9' C10' C11' 0.0 . . . . ?
C14' C9' C10' N2' -179.2(9) . . . . ?
C14' C9' N3' C8' -177.9(7) . . . . ?
C19' C18' C17' C16' 0.0 . . . . ?
C19' C18' C21' F1' 25.1(10) . . . . ?
C19' C18' C21' F2' -100.0(11) . . . . ?
C19' C18' C21' F3' 141.0(7) . . . . ?
C18' C19' C20' C15' 0.0 . . . . ?
C18' C17' C16' C15' 0.0 . . . . ?
C17' C18' C21' F1' -157.8(7) . . . . ?
C17' C18' C21' F2' 77.2(13) . . . . ?
C17' C18' C21' F3' -41.8(10) . . . . ?
C17' C16' C15' C8' -178.0(6) . . . . ?
C17' C16' C15' C20' 0.0 . . . . ?
C16' C15' C20' C19' 0.0 . . . . ?
C15' C8' N3' C9' 177.6(7) . . . . ?
C20' C19' C18' C17' 0.0 . . . . ?
C20' C19' C18' C21' 177.4(8) . . . . ?
C21' C18' C17' C16' -176.9(10) . . . . ?
N1' C5' C4' C3' -177.2(11) . . . . ?
N1' C7' C8' C15' -2.6(9) . . . . ?
N1' C7' C8' N3' 179.0(7) . . . . ?
N1' C7' N2' C6' 1.8(9) . . . . ?
N1' C7' N2' C10' -176.5(8) . . . . ?
N1'A C7'A C8'A C1F -1.0(13) . . . . ?
N1'A C7'A C8'A N3'A 174.6(11) . . . . ?
N1'A C7'A N2'A C1A -175.2(10) . . . . ?
N1'A C7'A N2'A C6'A -0.1(14) . . . . ?
N2' C6' C5' C4' 175.1(8) . . . . ?
N2' C6' C5' N1' -7.2(8) . . . . ?
N2' C7' C8' C15' -179.5(6) . . . . ?
N2' C7' C8' N3' 2.1(8) . . . . ?
N2' C7' N1' C5' -5.9(9) . . . . ?
N2' C10' C11' C12' 179.1(10) . . . . ?
N2'A C1A C9'A C1B 178.9(9) . . . . ?
N2'A C1A C9'A N3'A 6.2(12) . . . . ?
N2'A C6'A C1'A C2'A -178.3(16) . . . . ?
N2'A C6'A C5'A C4'A 178.7(13) . . . . ?
N2'A C6'A C5'A N1'A 2.5(12) . . . . ?
N2'A C7'A C8'A C1F 176.8(8) . . . . ?
N2'A C7'A C8'A N3'A -7.6(11) . . . . ?
N2'A C7'A N1'A C5'A 1.6(15) . . . . ?
N3' C8' C15' C16' 158.2(6) . . . . ?
N3' C8' C15' C20' -19.8(7) . . . . ?
N3' C9' C10' C11' 179.2(9) . . . . ?
N3' C9' C10' N2' 0.0(10) . . . . ?
N3' C9' C14' C13' -179.2(8) . . . . ?


_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 1.215
_oxdiff_exptl_absorpt_empirical_full_min 0.876
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
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 0.5444(15) 8459 5398 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4556(15) 8500 5398 nmt -0.0564 0.0003 -0.9427 -0.0000 -0.9997 -0.0001
-1.0581 0.0033 0.0563

_twin_special_details            
;
Component 2 rotated by -179.9597° 
 around [-0.67 -0.00 0.75] (reciprocal) or [-0.71 0.00 0.71] (direct)
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/dichloromethane'
