# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_ono034
_database_code_depnum_ccdc_archive 'CCDC 1951624'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-09-05 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_audit_creation_date             2019-09-05
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H31 Br2 Co N4 O2'
_chemical_formula_sum            'C17 H31 Br2 Co N4 O2'
_chemical_formula_weight         542.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Cu Br'
_chemical_oxdiff_usercomment     'Cui-san sample'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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'

_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                   8.0534(6)
_cell_length_b                   15.0332(12)
_cell_length_c                   17.7379(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.892(8)
_cell_angle_gamma                90
_cell_volume                     2121.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2973
_cell_measurement_temperature    93
_cell_measurement_theta_max      33.1140
_cell_measurement_theta_min      3.4220
_shelx_estimated_absorpt_T_max   0.546
_shelx_estimated_absorpt_T_min   0.169
_exptl_absorpt_coefficient_mu    4.594
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9584
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.643
_diffrn_ambient_temperature      93
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00 119.00   1.00    8.78    --   30.00  54.00 120.00  183
  2  ω    -18.00   9.00   1.00    8.78    --   30.00  54.00  60.00   27
  3  ω      7.00  59.00   1.00    8.78    --   30.00  54.00  30.00   52
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0573769000
_diffrn_orient_matrix_UB_12      -0.0020506000
_diffrn_orient_matrix_UB_13      0.0265821000
_diffrn_orient_matrix_UB_21      -0.0671266000
_diffrn_orient_matrix_UB_22      -0.0066420000
_diffrn_orient_matrix_UB_23      -0.0303654000
_diffrn_orient_matrix_UB_31      0.0120050000
_diffrn_orient_matrix_UB_32      -0.0466620000
_diffrn_orient_matrix_UB_33      0.0031433000
_diffrn_oxdiff_ac3_digest_frames 
;
01a0086d439651c17486cac05d8ffb48a0002622b26
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01b6686dd2677bc7e50fcfed49679914a296d6
;
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3778
_reflns_number_total             4331
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.667
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4331
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²+16.1710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1250
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C00H) \\sim Ueq, Uanis(C00P) \\sim Ueq, Uanis(C00R) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
Uanis(C00H) \\sim Ueq, Uanis(C0AA) \\sim Ueq, Uanis(C00S) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
3. Others
 Sof(H00I)=Sof(H00J)=Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(C00S)=Sof(H1AA)=Sof(HE)=
 Sof(HF)=1-FVAR(1)
 Sof(H00G)=Sof(H00H)=Sof(C00P)=Sof(H00Z)=Sof(HB)=Sof(C00R)=Sof(H00)=Sof(HC)=
 Sof(HD)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00E(H00C,H00D), C00F(H00E,H00F), C00H(H00G,H00H), C00H(H00I,
 H00J), C00I(H00K,H00L), C00K(H00P,H00Q), C00L(H00R,H00S), C00N(H00W,H00X),
 C00P(H00Z,HB), C0AA(H0AA,H0AB)
4.b Idealised Me refined as rotating group:
 C00J(H00M,H00N,H00O), C00M(H00T,H00U,H00V), C00O(H00Y,H,HA), C00R(H00,HC,HD),
 C00S(H1AA,HE,HF)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Br01 Br 0.76822(7) 0.77613(4) 0.18255(3) 0.01651(15) Uani 1 1 d . . . . .
Br02 Br 0.61301(7) 0.73461(4) 0.42804(3) 0.01748(15) Uani 1 1 d . . . . .
Co03 Co 0.69018(9) 0.75496(5) 0.30528(4) 0.01019(17) Uani 1 1 d . . . . .
O004 O 0.5296(5) 0.9230(3) 0.2947(2) 0.0198(9) Uani 1 1 d . . . . .
O005 O 0.8227(5) 0.9235(3) 0.3555(2) 0.0195(9) Uani 1 1 d . . . . .
N006 N 0.5127(6) 0.8365(3) 0.2805(3) 0.0137(9) Uani 1 1 d . . . . .
N007 N 0.8534(6) 0.8365(3) 0.3497(3) 0.0143(9) Uani 1 1 d . . . . .
N008 N 0.8741(5) 0.6742(3) 0.3314(3) 0.0132(9) Uani 1 1 d . . . . .
N009 N 0.5204(5) 0.6738(3) 0.2605(3) 0.0139(9) Uani 1 1 d . . . . .
C00A C 1.0107(6) 0.7100(4) 0.3661(3) 0.0143(11) Uani 1 1 d . . . . .
C00B C 0.5543(7) 0.5802(4) 0.2491(4) 0.0195(12) Uani 1 1 d . . . . .
H00A H 0.594095 0.572550 0.199424 0.023 Uiso 1 1 calc R . . . .
H00B H 0.448844 0.545865 0.247456 0.023 Uiso 1 1 calc R . . . .
C00C C 1.0015(7) 0.8062(4) 0.3781(3) 0.0151(11) Uani 1 1 d . . . . .
C00D C 0.3762(7) 0.7093(4) 0.2362(3) 0.0133(11) Uani 1 1 d . . . . .
C00E C 0.2260(7) 0.6592(4) 0.1965(3) 0.0166(11) Uani 1 1 d . . . . .
H00C H 0.123735 0.695423 0.197650 0.020 Uiso 1 1 calc R . . . .
H00D H 0.213441 0.603351 0.224596 0.020 Uiso 1 1 calc R . . . .
C00F C 0.2213(7) 0.8644(4) 0.2228(4) 0.0199(12) Uani 1 1 d . . . . .
H00E H 0.224888 0.915469 0.258223 0.024 Uiso 1 1 calc R . . . .
H00F H 0.116684 0.830766 0.225497 0.024 Uiso 1 1 calc R . . . .
C00G C 0.3689(6) 0.8056(4) 0.2477(3) 0.0143(11) Uani 1 1 d . . . . .
C00H C 1.1700(7) 0.6606(4) 0.3937(3) 0.0191(12) Uani 1 1 d . U . . .
H00G H 1.264680 0.693584 0.377340 0.023 Uiso 0.506(15) 1 calc R . P A 1
H00H H 1.164057 0.601752 0.368317 0.023 Uiso 0.506(15) 1 calc R . P A 1
H00I H 1.268436 0.697523 0.386994 0.023 Uiso 0.494(15) 1 calc R . P A 2
H00J H 1.174291 0.604961 0.364160 0.023 Uiso 0.494(15) 1 calc R . P A 2
C00I C 1.1354(7) 0.8647(4) 0.4195(3) 0.0208(12) Uani 1 1 d . . . . .
H00K H 1.142588 0.919909 0.389755 0.025 Uiso 1 1 calc R . . . .
H00L H 1.245067 0.833903 0.423736 0.025 Uiso 1 1 calc R . . . .
C00J C 1.1015(8) 0.8888(4) 0.4987(3) 0.0241(13) Uani 1 1 d . . . . .
H00M H 0.989980 0.916035 0.495098 0.036 Uiso 1 1 calc GR . . . .
H00N H 1.186901 0.930954 0.522236 0.036 Uiso 1 1 calc GR . . . .
H00O H 1.105612 0.834902 0.530070 0.036 Uiso 1 1 calc GR . . . .
C00K C 0.6846(7) 0.5438(4) 0.3117(4) 0.0199(12) Uani 1 1 d . . . . .
H00P H 0.687777 0.478235 0.306704 0.024 Uiso 1 1 calc R . . . .
H00Q H 0.649645 0.557531 0.361517 0.024 Uiso 1 1 calc R . . . .
C00L C 0.2399(7) 0.6368(4) 0.1134(3) 0.0217(13) Uani 1 1 d . . . . .
H00R H 0.256807 0.692214 0.085390 0.026 Uiso 1 1 calc R . . . .
H00S H 0.338806 0.598021 0.111944 0.026 Uiso 1 1 calc R . . . .
C00M C 0.0826(8) 0.5898(5) 0.0744(4) 0.0309(15) Uani 1 1 d . . . . .
H00T H 0.094134 0.576713 0.021374 0.046 Uiso 1 1 calc GR . . . .
H00U H -0.015245 0.628315 0.075504 0.046 Uiso 1 1 calc GR . . . .
H00V H 0.067376 0.534177 0.101327 0.046 Uiso 1 1 calc GR . . . .
C00N C 0.8599(7) 0.5799(4) 0.3116(4) 0.0218(13) Uani 1 1 d . . . . .
H00W H 0.940111 0.545683 0.348530 0.026 Uiso 1 1 calc R . . . .
H00X H 0.891499 0.571289 0.260329 0.026 Uiso 1 1 calc R . . . .
C00O C 0.2176(9) 0.8990(5) 0.1419(4) 0.0346(16) Uani 1 1 d . . . . .
H00Y H 0.197561 0.849418 0.105775 0.052 Uiso 1 1 calc GR . . . .
H H 0.325619 0.926993 0.137514 0.052 Uiso 1 1 calc GR . . . .
HA H 0.127313 0.942907 0.130322 0.052 Uiso 1 1 calc GR . . . .
C00P C 1.208(2) 0.6463(12) 0.4782(10) 0.019(4) Uani 0.506(15) 1 d . U P A 1
H00Z H 1.258370 0.702291 0.500779 0.023 Uiso 0.506(15) 1 calc R . P A 1
HB H 1.099516 0.638790 0.496718 0.023 Uiso 0.506(15) 1 calc R . P A 1
C00R C 1.3133(15) 0.5766(8) 0.5095(7) 0.025(3) Uani 0.506(15) 1 d . U P A 1
H00 H 1.276497 0.520780 0.483648 0.037 Uiso 0.506(15) 1 calc GR . P A 1
HC H 1.307087 0.571159 0.564079 0.037 Uiso 0.506(15) 1 calc GR . P A 1
HD H 1.429470 0.589193 0.502721 0.037 Uiso 0.506(15) 1 calc GR . P A 1
C0AA C 1.173(2) 0.6384(13) 0.4808(10) 0.023(5) Uani 0.494(15) 1 d . U P A 2
H0AA H 1.287534 0.616116 0.500151 0.027 Uiso 0.494(15) 1 calc R . P A 2
H0AB H 1.161590 0.695870 0.506828 0.027 Uiso 0.494(15) 1 calc R . P A 2
C00S C 1.0737(15) 0.5862(9) 0.5042(7) 0.024(3) Uani 0.494(15) 1 d . U P A 2
H1AA H 0.958355 0.607270 0.488524 0.036 Uiso 0.494(15) 1 calc GR . P A 2
HE H 1.097632 0.582899 0.560024 0.036 Uiso 0.494(15) 1 calc GR . P A 2
HF H 1.086225 0.526999 0.482613 0.036 Uiso 0.494(15) 1 calc GR . P A 2
H004 H 0.664(11) 0.933(6) 0.324(5) 0.06(3) Uiso 1 1 d . . . . .


_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
Br01 Co03 2.3786(9) . ?
Br02 Co03 2.3749(9) . ?
Co03 N006 1.883(5) . ?
Co03 N007 1.879(5) . ?
Co03 N008 1.916(4) . ?
Co03 N009 1.911(5) . ?
O004 N006 1.328(6) . ?
O004 H004 1.13(9) . ?
O005 N007 1.338(6) . ?
O005 H004 1.32(9) . ?
N006 C00G 1.299(7) . ?
N007 C00C 1.303(7) . ?
N008 C00A 1.291(7) . ?
N008 C00N 1.461(7) . ?
N009 C00B 1.455(7) . ?
N009 C00D 1.290(7) . ?
C00A C00C 1.465(8) . ?
C00A C00H 1.498(8) . ?
C00B H00A 0.9900 . ?
C00B H00B 0.9900 . ?
C00B C00K 1.507(8) . ?
C00C C00I 1.494(8) . ?
C00D C00E 1.505(7) . ?
C00D C00G 1.463(8) . ?
C00E H00C 0.9900 . ?
C00E H00D 0.9900 . ?
C00E C00L 1.533(8) . ?
C00F H00E 0.9900 . ?
C00F H00F 0.9900 . ?
C00F C00G 1.493(7) . ?
C00F C00O 1.522(9) . ?
C00H H00G 0.9900 . ?
C00H H00H 0.9900 . ?
C00H H00I 0.9900 . ?
C00H H00J 0.9900 . ?
C00H C00P 1.498(17) . ?
C00H C0AA 1.577(19) . ?
C00I H00K 0.9900 . ?
C00I H00L 0.9900 . ?
C00I C00J 1.516(8) . ?
C00J H00M 0.9800 . ?
C00J H00N 0.9800 . ?
C00J H00O 0.9800 . ?
C00K H00P 0.9900 . ?
C00K H00Q 0.9900 . ?
C00K C00N 1.513(8) . ?
C00L H00R 0.9900 . ?
C00L H00S 0.9900 . ?
C00L C00M 1.520(8) . ?
C00M H00T 0.9800 . ?
C00M H00U 0.9800 . ?
C00M H00V 0.9800 . ?
C00N H00W 0.9900 . ?
C00N H00X 0.9900 . ?
C00O H00Y 0.9800 . ?
C00O H 0.9800 . ?
C00O HA 0.9800 . ?
C00P H00Z 0.9900 . ?
C00P HB 0.9900 . ?
C00P C00R 1.41(2) . ?
C00R H00 0.9800 . ?
C00R HC 0.9800 . ?
C00R HD 0.9800 . ?
C0AA H0AA 0.9900 . ?
C0AA H0AB 0.9900 . ?
C0AA C00S 1.24(2) . ?
C00S H1AA 0.9800 . ?
C00S HE 0.9800 . ?
C00S HF 0.9800 . ?

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
Br02 Co03 Br01 179.67(4) . . ?
N006 Co03 Br01 89.85(14) . . ?
N006 Co03 Br02 90.08(14) . . ?
N006 Co03 N008 178.7(2) . . ?
N006 Co03 N009 81.36(19) . . ?
N007 Co03 Br01 91.69(14) . . ?
N007 Co03 Br02 88.00(14) . . ?
N007 Co03 N006 97.5(2) . . ?
N007 Co03 N008 81.2(2) . . ?
N007 Co03 N009 178.7(2) . . ?
N008 Co03 Br01 90.14(14) . . ?
N008 Co03 Br02 89.92(14) . . ?
N009 Co03 Br01 88.78(14) . . ?
N009 Co03 Br02 91.52(14) . . ?
N009 Co03 N008 99.98(19) . . ?
N006 O004 H004 106(5) . . ?
N007 O005 H004 105(4) . . ?
O004 N006 Co03 122.8(3) . . ?
C00G N006 Co03 117.6(4) . . ?
C00G N006 O004 119.6(5) . . ?
O005 N007 Co03 122.9(3) . . ?
C00C N007 Co03 118.3(4) . . ?
C00C N007 O005 118.8(5) . . ?
C00A N008 Co03 114.9(4) . . ?
C00A N008 C00N 123.2(5) . . ?
C00N N008 Co03 121.8(4) . . ?
C00B N009 Co03 122.5(3) . . ?
C00D N009 Co03 115.1(4) . . ?
C00D N009 C00B 122.2(5) . . ?
N008 C00A C00C 114.9(5) . . ?
N008 C00A C00H 125.0(5) . . ?
C00C C00A C00H 120.1(5) . . ?
N009 C00B H00A 109.2 . . ?
N009 C00B H00B 109.2 . . ?
N009 C00B C00K 111.9(5) . . ?
H00A C00B H00B 107.9 . . ?
C00K C00B H00A 109.2 . . ?
C00K C00B H00B 109.2 . . ?
N007 C00C C00A 110.6(5) . . ?
N007 C00C C00I 122.1(5) . . ?
C00A C00C C00I 127.2(5) . . ?
N009 C00D C00E 124.5(5) . . ?
N009 C00D C00G 114.6(5) . . ?
C00G C00D C00E 120.9(5) . . ?
C00D C00E H00C 109.0 . . ?
C00D C00E H00D 109.0 . . ?
C00D C00E C00L 112.8(4) . . ?
H00C C00E H00D 107.8 . . ?
C00L C00E H00C 109.0 . . ?
C00L C00E H00D 109.0 . . ?
H00E C00F H00F 107.9 . . ?
C00G C00F H00E 109.1 . . ?
C00G C00F H00F 109.1 . . ?
C00G C00F C00O 112.3(5) . . ?
C00O C00F H00E 109.1 . . ?
C00O C00F H00F 109.1 . . ?
N006 C00G C00D 111.4(5) . . ?
N006 C00G C00F 122.3(5) . . ?
C00D C00G C00F 126.3(5) . . ?
C00A C00H H00G 108.4 . . ?
C00A C00H H00H 108.4 . . ?
C00A C00H H00I 110.1 . . ?
C00A C00H H00J 110.1 . . ?
C00A C00H C00P 115.6(7) . . ?
C00A C00H C0AA 107.9(8) . . ?
H00G C00H H00H 107.5 . . ?
H00I C00H H00J 108.4 . . ?
C00P C00H H00G 108.4 . . ?
C00P C00H H00H 108.4 . . ?
C0AA C00H H00I 110.1 . . ?
C0AA C00H H00J 110.1 . . ?
C00C C00I H00K 109.2 . . ?
C00C C00I H00L 109.2 . . ?
C00C C00I C00J 112.1(5) . . ?
H00K C00I H00L 107.9 . . ?
C00J C00I H00K 109.2 . . ?
C00J C00I H00L 109.2 . . ?
C00I C00J H00M 109.5 . . ?
C00I C00J H00N 109.5 . . ?
C00I C00J H00O 109.5 . . ?
H00M C00J H00N 109.5 . . ?
H00M C00J H00O 109.5 . . ?
H00N C00J H00O 109.5 . . ?
C00B C00K H00P 108.7 . . ?
C00B C00K H00Q 108.7 . . ?
C00B C00K C00N 114.4(5) . . ?
H00P C00K H00Q 107.6 . . ?
C00N C00K H00P 108.7 . . ?
C00N C00K H00Q 108.7 . . ?
C00E C00L H00R 109.4 . . ?
C00E C00L H00S 109.4 . . ?
H00R C00L H00S 108.0 . . ?
C00M C00L C00E 111.0(5) . . ?
C00M C00L H00R 109.4 . . ?
C00M C00L H00S 109.4 . . ?
C00L C00M H00T 109.5 . . ?
C00L C00M H00U 109.5 . . ?
C00L C00M H00V 109.5 . . ?
H00T C00M H00U 109.5 . . ?
H00T C00M H00V 109.5 . . ?
H00U C00M H00V 109.5 . . ?
N008 C00N C00K 112.7(5) . . ?
N008 C00N H00W 109.0 . . ?
N008 C00N H00X 109.0 . . ?
C00K C00N H00W 109.0 . . ?
C00K C00N H00X 109.0 . . ?
H00W C00N H00X 107.8 . . ?
C00F C00O H00Y 109.5 . . ?
C00F C00O H 109.5 . . ?
C00F C00O HA 109.5 . . ?
H00Y C00O H 109.5 . . ?
H00Y C00O HA 109.5 . . ?
H C00O HA 109.5 . . ?
C00H C00P H00Z 107.0 . . ?
C00H C00P HB 107.0 . . ?
H00Z C00P HB 106.7 . . ?
C00R C00P C00H 121.4(13) . . ?
C00R C00P H00Z 107.0 . . ?
C00R C00P HB 107.0 . . ?
C00P C00R H00 109.5 . . ?
C00P C00R HC 109.5 . . ?
C00P C00R HD 109.5 . . ?
H00 C00R HC 109.5 . . ?
H00 C00R HD 109.5 . . ?
HC C00R HD 109.5 . . ?
C00H C0AA H0AA 106.5 . . ?
C00H C0AA H0AB 106.5 . . ?
H0AA C0AA H0AB 106.5 . . ?
C00S C0AA C00H 123.3(15) . . ?
C00S C0AA H0AA 106.5 . . ?
C00S C0AA H0AB 106.5 . . ?
C0AA C00S H1AA 109.5 . . ?
C0AA C00S HE 109.5 . . ?
C0AA C00S HF 109.5 . . ?
H1AA C00S HE 109.5 . . ?
H1AA C00S HF 109.5 . . ?
HE C00S HF 109.5 . . ?

_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 2.371
_oxdiff_exptl_absorpt_empirical_full_min 0.755
####################################################################### 
# 
# 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_ono064
_database_code_depnum_ccdc_archive 'CCDC 1966854'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_audit_creation_date             2019-11-01
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 F9 N'
_chemical_formula_sum            'C19 H12 F9 N'
_chemical_formula_weight         425.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N F'
_chemical_oxdiff_usercomment     'cui meindole-Ph-C4F7 -150deg'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7352(10)
_cell_length_b                   9.9728(11)
_cell_length_c                   11.1879(16)
_cell_angle_alpha                89.774(11)
_cell_angle_beta                 74.116(11)
_cell_angle_gamma                68.544(11)
_cell_volume                     867.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1646
_cell_measurement_temperature    123
_cell_measurement_theta_max      25.2230
_cell_measurement_theta_min      2.6970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8448
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         2.620
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   62.50    --   30.00  54.00-180.00  193
  2  ω    -74.00 119.00   1.00   62.50    --   30.00  54.00   0.00  193
  3  ω     48.00  75.00   1.00   62.50    --   30.00  54.00   0.00   27
  4  ω    -74.00 109.00   1.00   62.50    --   30.00  54.00 -60.00  183
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0061039000
_diffrn_orient_matrix_UB_12      0.0011701000
_diffrn_orient_matrix_UB_13      -0.0619528000
_diffrn_orient_matrix_UB_21      0.0902377000
_diffrn_orient_matrix_UB_22      -0.0382604000
_diffrn_orient_matrix_UB_23      -0.0232609000
_diffrn_orient_matrix_UB_31      -0.0120093000
_diffrn_orient_matrix_UB_32      -0.0666550000
_diffrn_orient_matrix_UB_33      0.0040507000
_diffrn_oxdiff_ac3_digest_frames 
;
01b102e1b35fc6c86c409ba75b231060db00596daaa
;
_diffrn_oxdiff_ac3_digest_hkl    
;
0128ac65799285fa52aa5404c904e977179e00
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2080
_reflns_number_total             3179
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.073
_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)+(0.0500P)²+0.0130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1201
_refine_special_details          ?
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
F1 F 0.48333(19) 0.43221(15) 0.80250(14) 0.0295(4) Uani 1 1 d . . . . .
F2 F 0.73980(18) 0.26896(16) 0.71636(13) 0.0293(4) Uani 1 1 d . . . . .
F3 F 0.37459(19) 0.21116(17) 0.88889(14) 0.0335(4) Uani 1 1 d . . . . .
F4 F 0.6372(2) 0.05733(15) 0.80816(14) 0.0319(4) Uani 1 1 d . . . . .
F5 F 0.5542(2) 0.11556(19) 1.04740(15) 0.0443(5) Uani 1 1 d . . . . .
F6 F 0.4640(2) 0.34858(19) 1.03937(15) 0.0432(5) Uani 1 1 d . . . . .
F7 F 0.8796(2) 0.1000(2) 0.90412(18) 0.0543(5) Uani 1 1 d . . . . .
F8 F 0.7822(2) 0.3326(2) 0.93066(16) 0.0479(5) Uani 1 1 d . . . . .
F9 F 0.7709(3) 0.2113(2) 1.08907(17) 0.0630(6) Uani 1 1 d . . . . .
N1 N 0.3821(3) 0.2948(2) 0.4935(2) 0.0259(5) Uani 1 1 d . . . . .
C1 C 0.3739(3) 0.3510(3) 0.6076(2) 0.0217(6) Uani 1 1 d . . . . .
C2 C 0.5187(3) 0.2656(3) 0.6389(2) 0.0206(6) Uani 1 1 d . . . . .
C3 C 0.6191(3) 0.1488(3) 0.5417(2) 0.0217(6) Uani 1 1 d . . . . .
C4 C 0.7741(3) 0.0297(3) 0.5200(2) 0.0271(6) Uani 1 1 d . . . . .
H4 H 0.837797 0.011971 0.578854 0.032 Uiso 1 1 calc R . . . .
C5 C 0.8326(4) -0.0617(3) 0.4111(3) 0.0311(7) Uani 1 1 d . . . . .
H5 H 0.937409 -0.143523 0.395602 0.037 Uiso 1 1 calc R . . . .
C6 C 0.7413(4) -0.0366(3) 0.3236(3) 0.0334(7) Uani 1 1 d . . . . .
H6 H 0.785259 -0.101388 0.249393 0.040 Uiso 1 1 calc R . . . .
C7 C 0.5890(4) 0.0802(3) 0.3425(2) 0.0311(7) Uani 1 1 d . . . . .
H7 H 0.526715 0.097394 0.282709 0.037 Uiso 1 1 calc R . . . .
C8 C 0.5294(3) 0.1719(3) 0.4520(2) 0.0237(6) Uani 1 1 d . . . . .
C9 C 0.2570(4) 0.3516(3) 0.4243(3) 0.0363(7) Uani 1 1 d . . . . .
H9A H 0.308392 0.387709 0.348356 0.054 Uiso 1 1 calc GR . . . .
H9B H 0.155532 0.430967 0.476543 0.054 Uiso 1 1 calc GR . . . .
H9C H 0.222772 0.274312 0.401412 0.054 Uiso 1 1 calc GR . . . .
C10 C 0.2246(3) 0.4802(3) 0.6767(2) 0.0238(6) Uani 1 1 d . . . . .
C11 C 0.1015(4) 0.4663(3) 0.7795(3) 0.0330(7) Uani 1 1 d . . . . .
H11 H 0.113365 0.372982 0.805057 0.040 Uiso 1 1 calc R . . . .
C12 C -0.0370(4) 0.5856(3) 0.8447(3) 0.0370(7) Uani 1 1 d . . . . .
H12 H -0.120367 0.574469 0.914745 0.044 Uiso 1 1 calc R . . . .
C13 C -0.0553(4) 0.7217(3) 0.8087(3) 0.0327(7) Uani 1 1 d . . . . .
H13 H -0.151023 0.804449 0.853740 0.039 Uiso 1 1 calc R . . . .
C14 C 0.0661(4) 0.7369(3) 0.7071(3) 0.0333(7) Uani 1 1 d . . . . .
H14 H 0.053930 0.830585 0.682428 0.040 Uiso 1 1 calc R . . . .
C15 C 0.2045(4) 0.6179(3) 0.6411(3) 0.0287(7) Uani 1 1 d . . . . .
H15 H 0.286870 0.629673 0.570693 0.034 Uiso 1 1 calc R . . . .
C16 C 0.5680(3) 0.2932(3) 0.7497(2) 0.0230(6) Uani 1 1 d . . . . .
C17 C 0.5412(3) 0.1962(3) 0.8550(2) 0.0241(6) Uani 1 1 d . . . . .
C18 C 0.5800(4) 0.2211(3) 0.9778(2) 0.0282(6) Uani 1 1 d . . . . .
C19 C 0.7566(4) 0.2163(4) 0.9744(3) 0.0377(8) Uani 1 1 d . . . . .


_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
F1 C16 1.355(3) . ?
F2 C16 1.371(3) . ?
F3 C17 1.350(3) . ?
F4 C17 1.346(3) . ?
F5 C18 1.355(3) . ?
F6 C18 1.342(3) . ?
F7 C19 1.324(3) . ?
F8 C19 1.327(3) . ?
F9 C19 1.321(3) . ?
N1 C1 1.370(3) . ?
N1 C8 1.377(3) . ?
N1 C9 1.457(3) . ?
C1 C2 1.379(3) . ?
C1 C10 1.478(4) . ?
C2 C3 1.432(3) . ?
C2 C16 1.475(3) . ?
C3 C4 1.396(4) . ?
C3 C8 1.405(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.373(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.389(4) . ?
C10 C15 1.390(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.372(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.372(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.544(3) . ?
C17 C18 1.544(4) . ?
C18 C19 1.516(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
C1 N1 C8 109.4(2) . . ?
C1 N1 C9 126.9(2) . . ?
C8 N1 C9 123.8(2) . . ?
N1 C1 C2 108.3(2) . . ?
N1 C1 C10 120.9(2) . . ?
C2 C1 C10 130.8(2) . . ?
C1 C2 C3 108.2(2) . . ?
C1 C2 C16 126.3(2) . . ?
C3 C2 C16 125.4(2) . . ?
C4 C3 C2 135.4(2) . . ?
C4 C3 C8 119.0(2) . . ?
C8 C3 C2 105.6(2) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 121.2 . . ?
C6 C7 C8 117.6(3) . . ?
C8 C7 H7 121.2 . . ?
N1 C8 C3 108.5(2) . . ?
N1 C8 C7 129.2(2) . . ?
C7 C8 C3 122.3(3) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 120.4(2) . . ?
C11 C10 C15 118.5(3) . . ?
C15 C10 C1 121.0(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.3(3) . . ?
C14 C15 H15 119.9 . . ?
F1 C16 F2 106.35(19) . . ?
F1 C16 C2 112.5(2) . . ?
F1 C16 C17 106.7(2) . . ?
F2 C16 C2 110.0(2) . . ?
F2 C16 C17 105.3(2) . . ?
C2 C16 C17 115.3(2) . . ?
F3 C17 C16 108.2(2) . . ?
F3 C17 C18 105.6(2) . . ?
F4 C17 F3 107.6(2) . . ?
F4 C17 C16 108.1(2) . . ?
F4 C17 C18 107.2(2) . . ?
C16 C17 C18 119.6(2) . . ?
F5 C18 C17 105.6(2) . . ?
F5 C18 C19 106.6(2) . . ?
F6 C18 F5 107.5(2) . . ?
F6 C18 C17 109.0(2) . . ?
F6 C18 C19 107.6(2) . . ?
C19 C18 C17 120.0(2) . . ?
F7 C19 F8 108.3(3) . . ?
F7 C19 C18 111.2(2) . . ?
F8 C19 C18 111.9(2) . . ?
F9 C19 F7 108.2(2) . . ?
F9 C19 F8 108.0(2) . . ?
F9 C19 C18 109.1(2) . . ?

_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 1.067
_oxdiff_exptl_absorpt_empirical_full_min 0.946
