# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1868691'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C49.88 H34.76 B Cl1.75 F12 N P'
_chemical_formula_weight         980.03

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7711(19)
_cell_length_b                   13.445(3)
_cell_length_c                   16.358(3)
_cell_angle_alpha                74.367(6)
_cell_angle_beta                 82.069(7)
_cell_angle_gamma                81.633(6)
_cell_volume                     2244.9(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2647
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      20.61

_exptl_crystal_description       shard
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             998
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.253
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6638
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23559
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.838
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_full        25.099
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             7896
_reflns_number_gt                4632
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep 3'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0887P)²+1.6923P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7896
_refine_ls_number_parameters     661
_refine_ls_number_restraints     101
_refine_ls_R_factor_all          0.1276
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.1878
_refine_ls_wR_factor_gt          0.1587
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
P001 P 2.39954(10) 1.77461(8) 0.37546(7) 0.0225(3) Uani 1 1 d . . . . .
F002 F 2.7472(2) 1.70234(17) 0.41861(15) 0.0315(6) Uani 1 1 d . . . . .
F003 F 2.8452(2) 1.47406(19) 0.39584(15) 0.0365(6) Uani 1 1 d . . . . .
F004 F 2.9029(2) 1.27309(19) 0.40169(16) 0.0426(7) Uani 1 1 d . . . . .
F005 F 2.5620(2) 1.99489(18) 0.22165(16) 0.0405(7) Uani 1 1 d . . . . .
F006 F 2.3308(2) 1.7436(2) 0.21506(16) 0.0451(7) Uani 1 1 d . . . . .
F007 F 2.8880(2) 1.82318(19) 0.45790(17) 0.0421(7) Uani 1 1 d . . . . .
F008 F 2.8659(3) 2.03240(19) 0.38348(17) 0.0460(7) Uani 1 1 d . . . . .
F009 F 2.6993(3) 2.11344(18) 0.26527(17) 0.0481(7) Uani 1 1 d . . . . .
F00A F 2.7297(3) 1.8669(2) 0.14055(16) 0.0463(7) Uani 1 1 d . . . . .
F00B F 2.2958(3) 1.7895(2) 0.05104(19) 0.0646(9) Uani 1 1 d . . . . .
F00C F 2.4757(3) 1.8777(2) -0.07057(17) 0.0670(10) Uani 1 1 d . . . . .
F00D F 2.6913(3) 1.9146(2) -0.02216(17) 0.0648(9) Uani 1 1 d . . . . .
N00E N 2.5438(3) 1.4261(3) 0.1420(2) 0.0318(9) Uani 1 1 d . . . . .
C00F C 2.8571(4) 1.3375(3) 0.3306(3) 0.0274(10) Uani 1 1 d . . . . .
C00G C 2.8286(4) 1.4418(3) 0.3268(3) 0.0257(9) Uani 1 1 d . . . . .
C00H C 2.2581(4) 1.4962(3) 0.4178(3) 0.0291(10) Uani 1 1 d . . . . .
H00A H 2.2908 1.4249 0.4283 0.035 Uiso 1 1 calc R U . . .
C00I C 2.3022(4) 1.8997(3) 0.3542(3) 0.0251(9) Uani 1 1 d . . . . .
C00J C 2.3399(4) 1.5712(3) 0.4069(3) 0.0273(10) Uani 1 1 d . . . . .
H00B H 2.4277 1.5507 0.4097 0.033 Uiso 1 1 calc R U . . .
C00K C 2.7707(4) 1.4736(3) 0.1880(3) 0.0236(9) Uani 1 1 d . . . . .
C00L C 2.4475(4) 1.7633(3) 0.4806(2) 0.0220(9) Uani 1 1 d . . . . .
C00M C 2.5264(4) 1.7501(3) 0.6392(3) 0.0337(11) Uani 1 1 d . . . . .
H00C H 2.5551 1.7450 0.6927 0.040 Uiso 1 1 calc R U . . .
C00N C 2.7832(4) 1.5135(3) 0.2565(3) 0.0225(9) Uani 1 1 d . . . . .
C00O C 2.4320(4) 1.6759(3) 0.5486(3) 0.0268(10) Uani 1 1 d . . . . .
H00D H 2.3947 1.6198 0.5406 0.032 Uiso 1 1 calc R U . . .
C00P C 2.5002(4) 1.8450(3) 0.4947(3) 0.0289(10) Uani 1 1 d . . . . .
H00E H 2.5085 1.9063 0.4499 0.035 Uiso 1 1 calc R U . . .
C00Q C 2.5407(4) 1.8383(3) 0.5730(3) 0.0307(10) Uani 1 1 d . . . . .
H00F H 2.5783 1.8941 0.5813 0.037 Uiso 1 1 calc R U . . .
C00R C 2.1320(4) 1.5239(3) 0.4137(3) 0.0325(11) Uani 1 1 d . . . . .
H00G H 2.0771 1.4721 0.4210 0.039 Uiso 1 1 calc R U . . .
C00S C 2.8065(4) 1.8654(3) 0.3989(3) 0.0305(10) Uani 1 1 d . . . . .
C00T C 2.2934(4) 1.6758(3) 0.3921(3) 0.0236(9) Uani 1 1 d . . . . .
C00U C 2.6469(4) 1.8398(3) 0.3154(2) 0.0241(9) Uani 1 1 d . . . . .
C00V C 2.7463(4) 1.6254(3) 0.2562(3) 0.0267(10) Uani 1 1 d . . . . .
H00H H 2.7454 1.6678 0.1964 0.032 Uiso 1 1 calc R U . . .
H00I H 2.8100 1.6492 0.2826 0.032 Uiso 1 1 calc R U . . .
C00W C 2.7334(4) 1.8036(3) 0.3761(3) 0.0250(9) Uani 1 1 d . . . . .
C00X C 2.7259(4) 1.5283(3) 0.1015(3) 0.0294(10) Uani 1 1 d . . . . .
H00J H 2.7533 1.5995 0.0794 0.035 Uiso 1 1 calc R U . . .
C00Y C 2.6153(4) 1.6430(3) 0.3051(3) 0.0248(9) Uani 1 1 d . . . . .
H00K H 2.6213 1.6130 0.3669 0.030 Uiso 1 1 calc R U . . .
H00L H 2.5556 1.6054 0.2872 0.030 Uiso 1 1 calc R U . . .
C00Z C 2.8405(4) 1.2980(3) 0.2638(3) 0.0279(10) Uani 1 1 d . . . . .
H00M H 2.8588 1.2259 0.2669 0.033 Uiso 1 1 calc R U . . .
C010 C 2.6410(4) 1.9467(3) 0.2811(3) 0.0291(10) Uani 1 1 d . . . . .
C011 C 2.7962(4) 1.3673(3) 0.1926(3) 0.0273(10) Uani 1 1 d . . . . .
C012 C 2.1645(4) 1.7041(3) 0.3876(3) 0.0320(10) Uani 1 1 d . . . . .
H01A H 2.1314 1.7753 0.3771 0.038 Uiso 1 1 calc R U . . .
C013 C 2.5301(4) 1.8043(3) 0.1883(3) 0.0259(10) Uani 1 1 d . . . . .
C014 C 2.0838(4) 1.6284(4) 0.3985(3) 0.0371(11) Uani 1 1 d . . . . .
H01B H 1.9958 1.6480 0.3956 0.045 Uiso 1 1 calc R U . . .
C015 C 2.4115(4) 1.4218(3) 0.1532(3) 0.0338(11) Uani 1 1 d . . . . .
C016 C 2.7639(4) 1.3505(3) 0.1102(3) 0.0321(11) Uani 1 1 d . . . . .
H01C H 2.8181 1.2902 0.0943 0.039 Uiso 1 1 calc R U . . .
C017 C 2.4703(4) 1.6697(3) 0.6273(3) 0.0318(11) Uani 1 1 d . . . . .
H01D H 2.4580 1.6101 0.6732 0.038 Uiso 1 1 calc R U . . .
C018 C 2.7957(4) 1.9701(3) 0.3623(3) 0.0325(11) Uani 1 1 d . . . . .
C019 C 2.2270(4) 1.9322(3) 0.4210(3) 0.0317(10) Uani 1 1 d . . . . .
H01E H 2.2255 1.8885 0.4774 0.038 Uiso 1 1 calc R U . . .
C01A C 2.1553(4) 2.0274(3) 0.4054(3) 0.0367(11) Uani 1 1 d . . . . .
H01F H 2.1029 2.0486 0.4508 0.044 Uiso 1 1 calc R U . . .
C01B C 2.6236(4) 1.3405(3) 0.1145(3) 0.0337(11) Uani 1 1 d . . . . .
H01G H 2.6034 1.3394 0.0575 0.040 Uiso 1 1 calc R U . . .
H01H H 2.6047 1.2737 0.1549 0.040 Uiso 1 1 calc R U . . .
C01C C 2.7118(4) 2.0107(3) 0.3028(3) 0.0325(11) Uani 1 1 d . . . . .
C01E C 2.3579(5) 1.3419(4) 0.1366(3) 0.0423(12) Uani 1 1 d . . . . .
H01I H 2.4103 1.2881 0.1168 0.051 Uiso 1 1 calc R U . . .
C01F C 2.4248(4) 1.7864(3) 0.1586(3) 0.0335(11) Uani 1 1 d . . . . .
C01G C 2.3028(4) 1.9642(3) 0.2724(3) 0.0385(12) Uani 1 1 d . . . . .
H01J H 2.3519 1.9423 0.2262 0.046 Uiso 1 1 calc R U . . .
C01H C 2.7912(5) 1.4536(3) 0.0475(3) 0.0388(12) Uani 1 1 d . . . . .
H01K H 2.7523 1.4650 -0.0062 0.047 Uiso 1 1 calc R U . . .
H01L H 2.8828 1.4591 0.0344 0.047 Uiso 1 1 calc R U . . .
C01I C 2.5836(4) 1.5302(3) 0.1058(3) 0.0311(10) Uani 1 1 d . . . . .
H01M H 2.5415 1.5770 0.1412 0.037 Uiso 1 1 calc R U . . .
H01N H 2.5570 1.5581 0.0476 0.037 Uiso 1 1 calc R U . . .
C01J C 2.6021(5) 1.8716(4) 0.0371(3) 0.0432(13) Uani 1 1 d . . . . .
C01K C 2.6184(5) 1.8469(3) 0.1230(3) 0.0344(11) Uani 1 1 d . . . . .
C01L C 2.2266(5) 1.3408(4) 0.1492(4) 0.0548(15) Uani 1 1 d . . . . .
H01O H 2.1906 1.2868 0.1368 0.066 Uiso 1 1 calc R U . . .
C01M C 2.3311(5) 1.4972(4) 0.1841(3) 0.0477(13) Uani 1 1 d . . . . .
H01P H 2.3652 1.5523 0.1962 0.057 Uiso 1 1 calc R U . . .
C01N C 2.1592(5) 2.0924(4) 0.3240(3) 0.0477(13) Uani 1 1 d . . . . .
H01Q H 2.1117 2.1591 0.3136 0.057 Uiso 1 1 calc R U . . .
C01O C 2.4937(6) 1.8531(4) 0.0126(3) 0.0452(13) Uani 1 1 d . . . . .
C01P C 2.1492(5) 1.4171(5) 0.1792(3) 0.0536(15) Uani 1 1 d . . . . .
H01R H 2.0602 1.4163 0.1869 0.064 Uiso 1 1 calc R U . . .
C01Q C 2.4043(5) 1.8094(4) 0.0733(3) 0.0421(12) Uani 1 1 d . . . . .
C01R C 2.2013(5) 1.4930(5) 0.1976(3) 0.0548(15) Uani 1 1 d . . . . .
H01S H 2.1485 1.5444 0.2201 0.066 Uiso 1 1 calc R U . . .
C01T C 2.2322(5) 2.0602(4) 0.2579(3) 0.0545(15) Uani 1 1 d . . . . .
H01T H 2.2340 2.1046 0.2018 0.065 Uiso 1 1 calc R U . . .
B01U B 2.5590(4) 1.7653(3) 0.2894(3) 0.0234(11) Uani 1 1 d . . . . .
Cl1A Cl 2.0151(8) 1.8582(5) 0.2075(5) 0.156(3) Uani 0.500(6) 1 d D U P A 1
Cl2A Cl 1.9596(5) 2.0662(4) 0.1299(3) 0.135(2) Uani 0.500(6) 1 d D U P A 1
C1A C 2.0330(18) 1.9512(5) 0.1158(7) 0.144(3) Uani 0.500(6) 1 d D U P A 1
H1AA H 1.9967 1.9326 0.0703 0.173 Uiso 0.500(6) 1 calc R U P A 1
H1AB H 2.1239 1.9569 0.0980 0.173 Uiso 0.500(6) 1 calc R U P A 1
Cl1B Cl 2.0148(12) 1.8123(9) 0.1916(6) 0.086(4) Uani 0.213(6) 1 d D U P B 2
Cl2B Cl 1.9854(8) 1.7215(6) 0.0640(6) 0.073(3) Uani 0.213(6) 1 d D U P B 2
C1B C 2.003(3) 1.8356(9) 0.0851(7) 0.080(4) Uani 0.213(6) 1 d D U P B 2
H1BA H 2.0804 1.8633 0.0520 0.096 Uiso 0.213(6) 1 calc R U P B 2
H1BB H 1.9300 1.8875 0.0687 0.096 Uiso 0.213(6) 1 calc R U P B 2
Cl1C Cl 2.0243(16) 1.7634(15) 0.1535(11) 0.135(6) Uani 0.164(6) 1 d D U P C 3
Cl2C Cl 1.9388(13) 1.7378(11) 0.0107(11) 0.106(6) Uani 0.164(6) 1 d D U P C 3
C1C C 2.021(5) 1.6770(19) 0.095(2) 0.119(6) Uani 0.164(6) 1 d D U P C 3
H1CC H 2.1085 1.6527 0.0746 0.143 Uiso 0.164(6) 1 calc R U P C 3
H1CA H 1.9806 1.6160 0.1304 0.143 Uiso 0.164(6) 1 calc R U P C 3


_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
P001 C00T 1.819(4) . ?
P001 C00I 1.822(4) . ?
P001 C00L 1.825(4) . ?
P001 B01U 2.077(5) . ?
F002 C00W 1.348(4) . ?
F003 C00G 1.355(5) . ?
F004 C00F 1.355(4) . ?
F005 C010 1.348(5) . ?
F006 C01F 1.355(5) . ?
F007 C00S 1.349(5) . ?
F008 C018 1.344(5) . ?
F009 C01C 1.347(4) . ?
F00A C01K 1.349(5) . ?
F00B C01Q 1.354(6) . ?
F00C C01O 1.345(5) . ?
F00D C01J 1.342(5) . ?
N00E C015 1.419(6) . ?
N00E C01B 1.466(5) . ?
N00E C01I 1.467(5) . ?
C00F C00G 1.377(6) . ?
C00F C00Z 1.380(6) . ?
C00G C00N 1.383(6) . ?
C00H C00R 1.361(6) . ?
C00H C00J 1.394(6) . ?
C00H H00A 0.9500 . ?
C00I C01G 1.385(6) . ?
C00I C019 1.397(6) . ?
C00J C00T 1.390(6) . ?
C00J H00B 0.9500 . ?
C00K C00N 1.397(5) . ?
C00K C011 1.398(6) . ?
C00K C00X 1.516(5) . ?
C00L C00P 1.392(6) . ?
C00L C00O 1.395(5) . ?
C00M C017 1.382(6) . ?
C00M C00Q 1.384(6) . ?
C00M H00C 0.9500 . ?
C00N C00V 1.498(5) . ?
C00O C017 1.384(6) . ?
C00O H00D 0.9500 . ?
C00P C00Q 1.386(6) . ?
C00P H00E 0.9500 . ?
C00Q H00F 0.9500 . ?
C00R C014 1.394(6) . ?
C00R H00G 0.9500 . ?
C00S C018 1.368(6) . ?
C00S C00W 1.375(6) . ?
C00T C012 1.392(6) . ?
C00U C010 1.390(5) . ?
C00U C00W 1.397(6) . ?
C00U B01U 1.643(6) . ?
C00V C00Y 1.542(6) . ?
C00V H00H 0.9900 . ?
C00V H00I 0.9900 . ?
C00X C01I 1.521(6) . ?
C00X C01H 1.545(6) . ?
C00X H00J 1.0000 . ?
C00Y B01U 1.632(6) . ?
C00Y H00K 0.9900 . ?
C00Y H00L 0.9900 . ?
C00Z C011 1.375(6) . ?
C00Z H00M 0.9500 . ?
C010 C01C 1.371(6) . ?
C011 C016 1.519(6) . ?
C012 C014 1.393(6) . ?
C012 H01A 0.9500 . ?
C013 C01F 1.368(6) . ?
C013 C01K 1.387(6) . ?
C013 B01U 1.653(6) . ?
C014 H01B 0.9500 . ?
C015 C01M 1.390(7) . ?
C015 C01E 1.394(6) . ?
C016 C01H 1.525(6) . ?
C016 C01B 1.527(6) . ?
C016 H01C 1.0000 . ?
C017 H01D 0.9500 . ?
C018 C01C 1.369(6) . ?
C019 C01A 1.375(6) . ?
C019 H01E 0.9500 . ?
C01A C01N 1.381(7) . ?
C01A H01F 0.9500 . ?
C01B H01G 0.9900 . ?
C01B H01H 0.9900 . ?
C01E C01L 1.402(7) . ?
C01E H01I 0.9500 . ?
C01F C01Q 1.387(6) . ?
C01G C01T 1.378(6) . ?
C01G H01J 0.9500 . ?
C01H H01K 0.9900 . ?
C01H H01L 0.9900 . ?
C01I H01M 0.9900 . ?
C01I H01N 0.9900 . ?
C01J C01O 1.362(7) . ?
C01J C01K 1.384(6) . ?
C01L C01P 1.378(8) . ?
C01L H01O 0.9500 . ?
C01M C01R 1.391(7) . ?
C01M H01P 0.9500 . ?
C01N C01T 1.375(7) . ?
C01N H01Q 0.9500 . ?
C01O C01Q 1.358(7) . ?
C01P C01R 1.351(8) . ?
C01P H01R 0.9500 . ?
C01R H01S 0.9500 . ?
C01T H01T 0.9500 . ?
Cl1A C1A 1.682(4) . ?
Cl2A C1A 1.690(4) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
Cl1B C1B 1.703(4) . ?
Cl2B C1B 1.703(4) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
Cl1C C1C 1.698(4) . ?
Cl2C C1C 1.697(4) . ?
C1C H1CC 0.9900 . ?
C1C H1CA 0.9900 . ?

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
C00T P001 C00I 106.55(19) . . ?
C00T P001 C00L 105.23(18) . . ?
C00I P001 C00L 102.61(18) . . ?
C00T P001 B01U 116.93(19) . . ?
C00I P001 B01U 114.80(19) . . ?
C00L P001 B01U 109.37(18) . . ?
C015 N00E C01B 117.1(4) . . ?
C015 N00E C01I 115.2(3) . . ?
C01B N00E C01I 116.4(3) . . ?
F004 C00F C00G 118.8(4) . . ?
F004 C00F C00Z 119.8(4) . . ?
C00G C00F C00Z 121.4(4) . . ?
F003 C00G C00F 117.8(4) . . ?
F003 C00G C00N 119.4(4) . . ?
C00F C00G C00N 122.8(4) . . ?
C00R C00H C00J 120.8(4) . . ?
C00R C00H H00A 119.6 . . ?
C00J C00H H00A 119.6 . . ?
C01G C00I C019 119.1(4) . . ?
C01G C00I P001 120.8(3) . . ?
C019 C00I P001 120.1(3) . . ?
C00T C00J C00H 120.3(4) . . ?
C00T C00J H00B 119.9 . . ?
C00H C00J H00B 119.9 . . ?
C00N C00K C011 121.8(4) . . ?
C00N C00K C00X 130.0(4) . . ?
C011 C00K C00X 108.2(3) . . ?
C00P C00L C00O 118.1(4) . . ?
C00P C00L P001 119.3(3) . . ?
C00O C00L P001 122.6(3) . . ?
C017 C00M C00Q 119.9(4) . . ?
C017 C00M H00C 120.0 . . ?
C00Q C00M H00C 120.0 . . ?
C00G C00N C00K 115.4(4) . . ?
C00G C00N C00V 121.6(4) . . ?
C00K C00N C00V 123.0(4) . . ?
C017 C00O C00L 121.0(4) . . ?
C017 C00O H00D 119.5 . . ?
C00L C00O H00D 119.5 . . ?
C00Q C00P C00L 121.0(4) . . ?
C00Q C00P H00E 119.5 . . ?
C00L C00P H00E 119.5 . . ?
C00M C00Q C00P 119.9(4) . . ?
C00M C00Q H00F 120.1 . . ?
C00P C00Q H00F 120.1 . . ?
C00H C00R C014 119.7(4) . . ?
C00H C00R H00G 120.1 . . ?
C014 C00R H00G 120.1 . . ?
F007 C00S C018 119.9(4) . . ?
F007 C00S C00W 120.1(4) . . ?
C018 C00S C00W 120.0(4) . . ?
C00J C00T C012 118.9(4) . . ?
C00J C00T P001 120.7(3) . . ?
C012 C00T P001 120.4(3) . . ?
C010 C00U C00W 112.4(4) . . ?
C010 C00U B01U 123.6(4) . . ?
C00W C00U B01U 123.9(3) . . ?
C00N C00V C00Y 112.1(3) . . ?
C00N C00V H00H 109.2 . . ?
C00Y C00V H00H 109.2 . . ?
C00N C00V H00I 109.2 . . ?
C00Y C00V H00I 109.2 . . ?
H00H C00V H00I 107.9 . . ?
F002 C00W C00S 115.3(4) . . ?
F002 C00W C00U 120.4(3) . . ?
C00S C00W C00U 124.4(4) . . ?
C00K C00X C01I 110.1(3) . . ?
C00K C00X C01H 101.0(3) . . ?
C01I C00X C01H 109.1(4) . . ?
C00K C00X H00J 112.0 . . ?
C01I C00X H00J 112.0 . . ?
C01H C00X H00J 112.0 . . ?
C00V C00Y B01U 113.4(3) . . ?
C00V C00Y H00K 108.9 . . ?
B01U C00Y H00K 108.9 . . ?
C00V C00Y H00L 108.9 . . ?
B01U C00Y H00L 108.9 . . ?
H00K C00Y H00L 107.7 . . ?
C011 C00Z C00F 117.3(4) . . ?
C011 C00Z H00M 121.3 . . ?
C00F C00Z H00M 121.3 . . ?
F005 C010 C01C 114.9(3) . . ?
F005 C010 C00U 120.4(4) . . ?
C01C C010 C00U 124.7(4) . . ?
C00Z C011 C00K 121.2(4) . . ?
C00Z C011 C016 131.1(4) . . ?
C00K C011 C016 107.8(4) . . ?
C00T C012 C014 120.3(4) . . ?
C00T C012 H01A 119.9 . . ?
C014 C012 H01A 119.9 . . ?
C01F C013 C01K 112.6(4) . . ?
C01F C013 B01U 124.3(4) . . ?
C01K C013 B01U 122.7(4) . . ?
C012 C014 C00R 120.0(4) . . ?
C012 C014 H01B 120.0 . . ?
C00R C014 H01B 120.0 . . ?
C01M C015 C01E 117.8(5) . . ?
C01M C015 N00E 120.0(4) . . ?
C01E C015 N00E 122.1(4) . . ?
C011 C016 C01H 101.0(3) . . ?
C011 C016 C01B 111.2(4) . . ?
C01H C016 C01B 108.4(4) . . ?
C011 C016 H01C 111.9 . . ?
C01H C016 H01C 111.9 . . ?
C01B C016 H01C 111.9 . . ?
C00M C017 C00O 120.0(4) . . ?
C00M C017 H01D 120.0 . . ?
C00O C017 H01D 120.0 . . ?
F008 C018 C00S 121.2(4) . . ?
F008 C018 C01C 120.3(4) . . ?
C00S C018 C01C 118.5(4) . . ?
C01A C019 C00I 120.2(4) . . ?
C01A C019 H01E 119.9 . . ?
C00I C019 H01E 119.9 . . ?
C019 C01A C01N 120.2(4) . . ?
C019 C01A H01F 119.9 . . ?
C01N C01A H01F 119.9 . . ?
N00E C01B C016 112.1(3) . . ?
N00E C01B H01G 109.2 . . ?
C016 C01B H01G 109.2 . . ?
N00E C01B H01H 109.2 . . ?
C016 C01B H01H 109.2 . . ?
H01G C01B H01H 107.9 . . ?
F009 C01C C018 120.0(4) . . ?
F009 C01C C010 120.0(4) . . ?
C018 C01C C010 120.0(4) . . ?
C015 C01E C01L 119.9(5) . . ?
C015 C01E H01I 120.0 . . ?
C01L C01E H01I 120.0 . . ?
F006 C01F C013 119.3(4) . . ?
F006 C01F C01Q 115.5(4) . . ?
C013 C01F C01Q 125.2(4) . . ?
C01T C01G C00I 120.0(4) . . ?
C01T C01G H01J 120.0 . . ?
C00I C01G H01J 120.0 . . ?
C016 C01H C00X 99.0(3) . . ?
C016 C01H H01K 112.0 . . ?
C00X C01H H01K 112.0 . . ?
C016 C01H H01L 112.0 . . ?
C00X C01H H01L 112.0 . . ?
H01K C01H H01L 109.7 . . ?
N00E C01I C00X 111.6(3) . . ?
N00E C01I H01M 109.3 . . ?
C00X C01I H01M 109.3 . . ?
N00E C01I H01N 109.3 . . ?
C00X C01I H01N 109.3 . . ?
H01M C01I H01N 108.0 . . ?
F00D C01J C01O 119.7(4) . . ?
F00D C01J C01K 120.7(5) . . ?
C01O C01J C01K 119.6(4) . . ?
F00A C01K C01J 115.0(4) . . ?
F00A C01K C013 120.6(4) . . ?
C01J C01K C013 124.4(5) . . ?
C01P C01L C01E 120.9(5) . . ?
C01P C01L H01O 119.5 . . ?
C01E C01L H01O 119.5 . . ?
C015 C01M C01R 120.9(5) . . ?
C015 C01M H01P 119.5 . . ?
C01R C01M H01P 119.5 . . ?
C01T C01N C01A 119.7(4) . . ?
C01T C01N H01Q 120.1 . . ?
C01A C01N H01Q 120.1 . . ?
F00C C01O C01Q 120.6(5) . . ?
F00C C01O C01J 120.4(5) . . ?
C01Q C01O C01J 119.0(4) . . ?
C01R C01P C01L 119.1(5) . . ?
C01R C01P H01R 120.4 . . ?
C01L C01P H01R 120.4 . . ?
F00B C01Q C01O 120.4(4) . . ?
F00B C01Q C01F 120.3(5) . . ?
C01O C01Q C01F 119.3(5) . . ?
C01P C01R C01M 121.2(5) . . ?
C01P C01R H01S 119.4 . . ?
C01M C01R H01S 119.4 . . ?
C01N C01T C01G 120.7(5) . . ?
C01N C01T H01T 119.7 . . ?
C01G C01T H01T 119.7 . . ?
C00Y B01U C00U 115.5(3) . . ?
C00Y B01U C013 105.8(3) . . ?
C00U B01U C013 113.2(3) . . ?
C00Y B01U P001 107.5(3) . . ?
C00U B01U P001 101.1(3) . . ?
C013 B01U P001 113.9(3) . . ?
Cl1A C1A Cl2A 109.7(5) . . ?
Cl1A C1A H1AA 109.7 . . ?
Cl2A C1A H1AA 109.7 . . ?
Cl1A C1A H1AB 109.7 . . ?
Cl2A C1A H1AB 109.7 . . ?
H1AA C1A H1AB 108.2 . . ?
Cl1B C1B Cl2B 108.2(6) . . ?
Cl1B C1B H1BA 110.1 . . ?
Cl2B C1B H1BA 110.1 . . ?
Cl1B C1B H1BB 110.1 . . ?
Cl2B C1B H1BB 110.1 . . ?
H1BA C1B H1BB 108.4 . . ?
Cl2C C1C Cl1C 108.0(10) . . ?
Cl2C C1C H1CC 110.1 . . ?
Cl1C C1C H1CC 110.1 . . ?
Cl2C C1C H1CA 110.1 . . ?
Cl1C C1C H1CA 110.1 . . ?
H1CC C1C H1CA 108.4 . . ?

_refine_diff_density_max         0.875
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_d18140a_a
_database_code_depnum_ccdc_archive 'CCDC 1868693'
_audit_update_record             
;
2018-09-19 deposited with the CCDC.
2018-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H32 B F2 N'
_chemical_formula_sum            'C27 H32 B F2 N'
_chemical_formula_weight         419.34

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'
B B 0.0090 0.0039 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   25.1437(8)
_cell_length_b                   10.9915(4)
_cell_length_c                   7.9724(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2203.31(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      66.35

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.664
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6757
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46674
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.516
_diffrn_reflns_theta_max         67.343
_diffrn_reflns_theta_full        67.343
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3881
_reflns_number_gt                3712
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_max     0.975
_reflns_Friedel_fraction_full    0.975

_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. 
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²+0.4738P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1645 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3881
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.75805(6) 0.41828(12) 0.5086(2) 0.0400(4) Uani 1 1 d . . . . .
F2 F 0.83700(5) 0.55357(14) 0.6279(2) 0.0436(4) Uani 1 1 d . . . . .
N1 N 0.66904(8) 0.92052(17) 0.5394(2) 0.0270(4) Uani 1 1 d . . . . .
C1 C 0.55170(11) 0.2349(3) 0.7666(4) 0.0494(7) Uani 1 1 d . . . . .
H1A H 0.577684 0.225104 0.860579 0.059 Uiso 1 1 calc R U . . .
C2 C 0.54838(14) 0.1165(3) 0.6687(6) 0.0685(11) Uani 1 1 d . . . . .
H2A H 0.584852 0.091959 0.636447 0.082 Uiso 1 1 calc R U . . .
H2B H 0.534079 0.052693 0.743826 0.082 Uiso 1 1 calc R U . . .
C3 C 0.51488(17) 0.1208(3) 0.5141(7) 0.0770(12) Uani 1 1 d . . . . .
H3A H 0.476965 0.121540 0.547568 0.092 Uiso 1 1 calc R U . . .
H3B H 0.521148 0.045703 0.448399 0.092 Uiso 1 1 calc R U . . .
C4 C 0.52568(17) 0.2314(4) 0.4011(5) 0.0750(12) Uani 1 1 d . . . . .
H4A H 0.495812 0.239876 0.321063 0.090 Uiso 1 1 calc R U . . .
H4B H 0.558269 0.215457 0.334988 0.090 Uiso 1 1 calc R U . . .
C5 C 0.53275(11) 0.3544(3) 0.4960(4) 0.0510(8) Uani 1 1 d . . . . .
H5A H 0.547325 0.416926 0.417221 0.061 Uiso 1 1 calc R U . . .
C6 C 0.48084(15) 0.4018(3) 0.5740(5) 0.0574(8) Uani 1 1 d . . . . .
H6A H 0.487508 0.483597 0.621419 0.069 Uiso 1 1 calc R U . . .
H6B H 0.454038 0.410790 0.483862 0.069 Uiso 1 1 calc R U . . .
C7 C 0.45791(12) 0.3221(3) 0.7096(5) 0.0565(8) Uani 1 1 d . . . . .
H7A H 0.440818 0.250706 0.656444 0.068 Uiso 1 1 calc R U . . .
H7B H 0.429853 0.368216 0.769188 0.068 Uiso 1 1 calc R U . . .
C8 C 0.49826(14) 0.2771(3) 0.8378(5) 0.0564(8) Uani 1 1 d . . . . .
H8A H 0.482217 0.208601 0.900569 0.068 Uiso 1 1 calc R U . . .
H8B H 0.505041 0.343429 0.919047 0.068 Uiso 1 1 calc R U . . .
C9 C 0.62739(10) 0.3982(2) 0.6684(4) 0.0383(6) Uani 1 1 d . . . . .
H9A H 0.624481 0.446056 0.773217 0.046 Uiso 1 1 calc R U . . .
H9B H 0.654764 0.334951 0.687765 0.046 Uiso 1 1 calc R U . . .
C10 C 0.64811(10) 0.4831(2) 0.5316(3) 0.0331(5) Uani 1 1 d . . . . .
H10A H 0.660551 0.433923 0.435227 0.040 Uiso 1 1 calc R U . . .
H10B H 0.618666 0.535559 0.492042 0.040 Uiso 1 1 calc R U . . .
C11 C 0.69276(9) 0.5615(2) 0.5923(3) 0.0267(5) Uani 1 1 d . . . . .
C12 C 0.74550(9) 0.5255(2) 0.5830(3) 0.0289(5) Uani 1 1 d . . . . .
C13 C 0.78634(9) 0.5958(2) 0.6462(3) 0.0322(5) Uani 1 1 d . . . . .
C14 C 0.77722(9) 0.7048(2) 0.7263(3) 0.0314(5) Uani 1 1 d . . . . .
H14A H 0.805565 0.752778 0.769228 0.038 Uiso 1 1 calc R U . . .
C15 C 0.72478(9) 0.7410(2) 0.7412(3) 0.0281(5) Uani 1 1 d . . . . .
C16 C 0.68363(9) 0.6725(2) 0.6724(3) 0.0262(5) Uani 1 1 d . . . . .
C17 C 0.63225(9) 0.7424(2) 0.6972(3) 0.0289(5) Uani 1 1 d . . . . .
H17A H 0.600928 0.687098 0.709903 0.035 Uiso 1 1 calc R U . . .
C18 C 0.62461(9) 0.8341(2) 0.5545(3) 0.0281(5) Uani 1 1 d . . . . .
H18A H 0.620736 0.789280 0.447415 0.034 Uiso 1 1 calc R U . . .
H18B H 0.591306 0.880015 0.573889 0.034 Uiso 1 1 calc R U . . .
C19 C 0.69856(10) 0.9570(2) 0.6907(3) 0.0321(5) Uani 1 1 d . . . . .
H19A H 0.681035 1.028653 0.741701 0.038 Uiso 1 1 calc R U . . .
H19B H 0.735117 0.980975 0.658590 0.038 Uiso 1 1 calc R U . . .
C20 C 0.70128(11) 0.8547(2) 0.8199(3) 0.0330(5) Uani 1 1 d . . . . .
H20A H 0.720814 0.879739 0.923503 0.040 Uiso 1 1 calc R U . . .
C21 C 0.64417(11) 0.8126(3) 0.8582(3) 0.0369(6) Uani 1 1 d . . . . .
H21A H 0.642723 0.759445 0.958351 0.044 Uiso 1 1 calc R U . . .
H21B H 0.619695 0.882297 0.873479 0.044 Uiso 1 1 calc R U . . .
C22 C 0.66642(9) 1.0061(2) 0.4096(3) 0.0264(5) Uani 1 1 d . . . . .
C23 C 0.69867(10) 1.1110(2) 0.4108(3) 0.0314(5) Uani 1 1 d . . . . .
H23A H 0.721501 1.125811 0.503533 0.038 Uiso 1 1 calc R U . . .
C24 C 0.69749(11) 1.1928(2) 0.2784(3) 0.0346(6) Uani 1 1 d . . . . .
H24A H 0.719990 1.262223 0.281176 0.041 Uiso 1 1 calc R U . . .
C25 C 0.66416(11) 1.1753(2) 0.1422(3) 0.0376(6) Uani 1 1 d . . . . .
H25A H 0.663612 1.231516 0.051743 0.045 Uiso 1 1 calc R U . . .
C26 C 0.63177(11) 1.0739(2) 0.1414(3) 0.0384(6) Uani 1 1 d . . . . .
H26A H 0.608417 1.061039 0.049463 0.046 Uiso 1 1 calc R U . . .
C27 C 0.63252(10) 0.9905(2) 0.2717(3) 0.0318(5) Uani 1 1 d . . . . .
H27A H 0.609702 0.921713 0.267547 0.038 Uiso 1 1 calc R U . . .
B1 B 0.57325(12) 0.3322(3) 0.6406(4) 0.0397(7) 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 C12 1.356(3) . ?
F2 C13 1.363(3) . ?
N1 C22 1.400(3) . ?
N1 C19 1.472(3) . ?
N1 C18 1.472(3) . ?
C1 C2 1.519(5) . ?
C1 C8 1.531(5) . ?
C1 B1 1.564(4) . ?
C1 H1A 1.0000 . ?
C2 C3 1.494(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.538(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.559(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.536(5) . ?
C5 B1 1.558(4) . ?
C5 H5A 1.0000 . ?
C6 C7 1.507(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.522(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.527(4) . ?
C9 B1 1.558(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.496(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.386(3) . ?
C11 C16 1.396(3) . ?
C12 C13 1.380(4) . ?
C13 C14 1.378(4) . ?
C14 C15 1.382(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.393(3) . ?
C15 C20 1.517(4) . ?
C16 C17 1.516(3) . ?
C17 C21 1.528(4) . ?
C17 C18 1.532(3) . ?
C17 H17A 1.0000 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.526(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.539(4) . ?
C20 H20A 1.0000 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.402(3) . ?
C22 C23 1.409(3) . ?
C23 C24 1.387(4) . ?
C23 H23A 0.9500 . ?
C24 C25 1.385(4) . ?
C24 H24A 0.9500 . ?
C25 C26 1.380(4) . ?
C25 H25A 0.9500 . ?
C26 C27 1.386(4) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?

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
C22 N1 C19 116.52(18) . . ?
C22 N1 C18 117.27(18) . . ?
C19 N1 C18 119.47(19) . . ?
C2 C1 C8 113.7(3) . . ?
C2 C1 B1 105.9(3) . . ?
C8 C1 B1 109.6(2) . . ?
C2 C1 H1A 109.2 . . ?
C8 C1 H1A 109.2 . . ?
B1 C1 H1A 109.2 . . ?
C3 C2 C1 115.3(3) . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C2 C3 C4 114.1(3) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C5 115.0(3) . . ?
C3 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
C5 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
C6 C5 B1 108.0(3) . . ?
C6 C5 C4 113.1(3) . . ?
B1 C5 C4 107.3(3) . . ?
C6 C5 H5A 109.4 . . ?
B1 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C7 C6 C5 114.8(3) . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 C8 114.6(3) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C1 115.8(3) . . ?
C7 C8 H8A 108.3 . . ?
C1 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
C1 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 B1 118.7(2) . . ?
C10 C9 H9A 107.6 . . ?
B1 C9 H9A 107.6 . . ?
C10 C9 H9B 107.6 . . ?
B1 C9 H9B 107.6 . . ?
H9A C9 H9B 107.1 . . ?
C11 C10 C9 112.2(2) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C16 115.6(2) . . ?
C12 C11 C10 122.4(2) . . ?
C16 C11 C10 121.9(2) . . ?
F1 C12 C13 118.2(2) . . ?
F1 C12 C11 119.6(2) . . ?
C13 C12 C11 122.2(2) . . ?
F2 C13 C14 120.1(2) . . ?
F2 C13 C12 117.8(2) . . ?
C14 C13 C12 122.2(2) . . ?
C13 C14 C15 116.7(2) . . ?
C13 C14 H14A 121.7 . . ?
C15 C14 H14A 121.7 . . ?
C14 C15 C16 121.3(2) . . ?
C14 C15 C20 130.1(2) . . ?
C16 C15 C20 108.6(2) . . ?
C15 C16 C11 122.1(2) . . ?
C15 C16 C17 107.9(2) . . ?
C11 C16 C17 130.0(2) . . ?
C16 C17 C21 101.4(2) . . ?
C16 C17 C18 110.09(19) . . ?
C21 C17 C18 108.45(19) . . ?
C16 C17 H17A 112.1 . . ?
C21 C17 H17A 112.1 . . ?
C18 C17 H17A 112.1 . . ?
N1 C18 C17 112.95(19) . . ?
N1 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
N1 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
N1 C19 C20 112.02(19) . . ?
N1 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
N1 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C15 C20 C19 110.20(19) . . ?
C15 C20 C21 101.43(19) . . ?
C19 C20 C21 108.3(2) . . ?
C15 C20 H20A 112.1 . . ?
C19 C20 H20A 112.1 . . ?
C21 C20 H20A 112.1 . . ?
C17 C21 C20 99.65(19) . . ?
C17 C21 H21A 111.8 . . ?
C20 C21 H21A 111.8 . . ?
C17 C21 H21B 111.8 . . ?
C20 C21 H21B 111.8 . . ?
H21A C21 H21B 109.6 . . ?
N1 C22 C27 121.8(2) . . ?
N1 C22 C23 121.2(2) . . ?
C27 C22 C23 117.0(2) . . ?
C24 C23 C22 120.9(2) . . ?
C24 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
C25 C24 C23 121.3(2) . . ?
C25 C24 H24A 119.4 . . ?
C23 C24 H24A 119.4 . . ?
C26 C25 C24 118.2(2) . . ?
C26 C25 H25A 120.9 . . ?
C24 C25 H25A 120.9 . . ?
C25 C26 C27 121.5(2) . . ?
C25 C26 H26A 119.2 . . ?
C27 C26 H26A 119.2 . . ?
C26 C27 C22 121.1(2) . . ?
C26 C27 H27A 119.5 . . ?
C22 C27 H27A 119.5 . . ?
C5 B1 C9 127.1(3) . . ?
C5 B1 C1 110.9(2) . . ?
C9 B1 C1 122.0(3) . . ?

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
C8 C1 C2 C3 63.4(4) . . . . ?
B1 C1 C2 C3 -57.0(4) . . . . ?
C1 C2 C3 C4 47.1(4) . . . . ?
C2 C3 C4 C5 -42.5(5) . . . . ?
C3 C4 C5 C6 -70.0(4) . . . . ?
C3 C4 C5 B1 49.0(4) . . . . ?
B1 C5 C6 C7 -54.5(4) . . . . ?
C4 C5 C6 C7 64.1(4) . . . . ?
C5 C6 C7 C8 45.5(4) . . . . ?
C6 C7 C8 C1 -42.2(4) . . . . ?
C2 C1 C8 C7 -70.3(4) . . . . ?
B1 C1 C8 C7 48.0(4) . . . . ?
B1 C9 C10 C11 166.2(2) . . . . ?
C9 C10 C11 C12 89.1(3) . . . . ?
C9 C10 C11 C16 -86.5(3) . . . . ?
C16 C11 C12 F1 179.38(19) . . . . ?
C10 C11 C12 F1 3.5(3) . . . . ?
C16 C11 C12 C13 -1.1(3) . . . . ?
C10 C11 C12 C13 -176.9(2) . . . . ?
F1 C12 C13 F2 0.8(3) . . . . ?
C11 C12 C13 F2 -178.7(2) . . . . ?
F1 C12 C13 C14 -178.8(2) . . . . ?
C11 C12 C13 C14 1.6(4) . . . . ?
F2 C13 C14 C15 -179.5(2) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C16 -2.5(3) . . . . ?
C13 C14 C15 C20 -179.5(2) . . . . ?
C14 C15 C16 C11 3.1(3) . . . . ?
C20 C15 C16 C11 -179.3(2) . . . . ?
C14 C15 C16 C17 -175.0(2) . . . . ?
C20 C15 C16 C17 2.5(2) . . . . ?
C12 C11 C16 C15 -1.2(3) . . . . ?
C10 C11 C16 C15 174.6(2) . . . . ?
C12 C11 C16 C17 176.4(2) . . . . ?
C10 C11 C16 C17 -7.7(4) . . . . ?
C15 C16 C17 C21 -29.5(2) . . . . ?
C11 C16 C17 C21 152.5(2) . . . . ?
C15 C16 C17 C18 85.2(2) . . . . ?
C11 C16 C17 C18 -92.8(3) . . . . ?
C22 N1 C18 C17 178.37(19) . . . . ?
C19 N1 C18 C17 -31.4(3) . . . . ?
C16 C17 C18 N1 -57.5(3) . . . . ?
C21 C17 C18 N1 52.6(3) . . . . ?
C22 N1 C19 C20 -177.1(2) . . . . ?
C18 N1 C19 C20 32.5(3) . . . . ?
C14 C15 C20 C19 88.0(3) . . . . ?
C16 C15 C20 C19 -89.3(2) . . . . ?
C14 C15 C20 C21 -157.5(2) . . . . ?
C16 C15 C20 C21 25.2(2) . . . . ?
N1 C19 C20 C15 55.3(3) . . . . ?
N1 C19 C20 C21 -54.8(3) . . . . ?
C16 C17 C21 C20 43.4(2) . . . . ?
C18 C17 C21 C20 -72.5(2) . . . . ?
C15 C20 C21 C17 -41.8(2) . . . . ?
C19 C20 C21 C17 74.1(2) . . . . ?
C19 N1 C22 C27 -169.3(2) . . . . ?
C18 N1 C22 C27 -18.2(3) . . . . ?
C19 N1 C22 C23 11.8(3) . . . . ?
C18 N1 C22 C23 163.0(2) . . . . ?
N1 C22 C23 C24 177.3(2) . . . . ?
C27 C22 C23 C24 -1.6(3) . . . . ?
C22 C23 C24 C25 1.0(4) . . . . ?
C23 C24 C25 C26 0.2(4) . . . . ?
C24 C25 C26 C27 -0.6(4) . . . . ?
C25 C26 C27 C22 -0.1(4) . . . . ?
N1 C22 C27 C26 -177.7(2) . . . . ?
C23 C22 C27 C26 1.2(4) . . . . ?
C6 C5 B1 C9 -116.7(3) . . . . ?
C4 C5 B1 C9 121.0(3) . . . . ?
C6 C5 B1 C1 60.9(3) . . . . ?
C4 C5 B1 C1 -61.4(3) . . . . ?
C10 C9 B1 C5 -8.4(5) . . . . ?
C10 C9 B1 C1 174.3(3) . . . . ?
C2 C1 B1 C5 65.0(3) . . . . ?
C8 C1 B1 C5 -58.0(4) . . . . ?
C2 C1 B1 C9 -117.3(3) . . . . ?
C8 C1 B1 C9 119.7(3) . . . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1868692'
_audit_update_record             
;
2018-09-19 deposited with the CCDC.
2018-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38.50 H33.50 B F12 N O'
_chemical_formula_weight         764.97

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   31.615(3)
_cell_length_b                   11.1961(9)
_cell_length_c                   22.1924(18)
_cell_angle_alpha                90
_cell_angle_beta                 118.058(4)
_cell_angle_gamma                90
_cell_volume                     6932.1(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7964
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      25.86

_exptl_crystal_description       shard
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             3140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6796
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54014
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.596
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7366
_reflns_number_gt                4633
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep 3'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+6.0925P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7366
_refine_ls_number_parameters     493
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
B1 B 0.86673(8) 1.8394(2) 0.49148(12) 0.0233(5) Uani 1 1 d . . . . .
H1 H 0.6362(8) 1.600(2) 0.3752(11) 0.028 Uiso 1 1 d . U . . .
N1 N 0.63393(6) 1.55283(16) 0.33930(9) 0.0253(4) Uani 1 1 d . . . . .
H2 H 0.8813(8) 1.756(2) 0.5760(12) 0.030 Uiso 1 1 d . U . . .
O1 O 0.87030(5) 1.81943(14) 0.56061(7) 0.0259(3) Uani 1 1 d . . . . .
F1 F 0.87180(5) 1.82788(12) 0.36351(7) 0.0422(4) Uani 1 1 d . . . . .
F2 F 0.90186(7) 1.64917(14) 0.31527(9) 0.0673(5) Uani 1 1 d . . . . .
F3 F 0.93676(8) 1.44581(14) 0.38886(11) 0.0795(6) Uani 1 1 d . . . . .
F4 F 0.93692(7) 1.42291(14) 0.51194(9) 0.0697(5) Uani 1 1 d . . . . .
F5 F 0.90299(5) 1.59449(12) 0.55819(7) 0.0467(4) Uani 1 1 d . . . . .
F6 F 0.96621(4) 1.85965(13) 0.60040(7) 0.0434(4) Uani 1 1 d . . . . .
F7 F 1.02851(5) 2.03356(14) 0.62006(7) 0.0514(4) Uani 1 1 d . . . . .
F8 F 1.00529(5) 2.21654(13) 0.52911(8) 0.0497(4) Uani 1 1 d . . . . .
F9 F 0.91667(5) 2.22202(12) 0.41850(7) 0.0489(4) Uani 1 1 d . . . . .
F10 F 0.85254(4) 2.05765(12) 0.40066(6) 0.0377(3) Uani 1 1 d . . . . .
F11 F 0.64852(5) 2.07724(11) 0.39610(7) 0.0424(4) Uani 1 1 d . . . . .
F12 F 0.73628(4) 1.99555(11) 0.47379(7) 0.0357(3) Uani 1 1 d . . . . .
C1 C 0.88527(7) 1.72208(19) 0.46397(11) 0.0254(5) Uani 1 1 d . . . . .
C2 C 0.88632(8) 1.7273(2) 0.40186(12) 0.0311(5) Uani 1 1 d . . . . .
C3 C 0.90233(10) 1.6369(2) 0.37594(13) 0.0405(6) Uani 1 1 d . . . . .
C4 C 0.91995(10) 1.5344(2) 0.41282(15) 0.0471(7) Uani 1 1 d . . . . .
C5 C 0.92020(10) 1.5227(2) 0.47477(14) 0.0428(6) Uani 1 1 d . . . . .
C6 C 0.90243(8) 1.6154(2) 0.49737(12) 0.0315(5) Uani 1 1 d . . . . .
C7 C 0.90487(7) 1.94928(19) 0.49996(10) 0.0235(5) Uani 1 1 d . . . . .
C8 C 0.95103(8) 1.9504(2) 0.55447(11) 0.0285(5) Uani 1 1 d . . . . .
C9 C 0.98436(7) 2.0386(2) 0.56548(12) 0.0332(5) Uani 1 1 d . . . . .
C10 C 0.97285(8) 2.1314(2) 0.51998(12) 0.0334(6) Uani 1 1 d . . . . .
C11 C 0.92828(8) 2.1340(2) 0.46487(11) 0.0307(5) Uani 1 1 d . . . . .
C12 C 0.89570(7) 2.0453(2) 0.45666(11) 0.0274(5) Uani 1 1 d . . . . .
C30 C 0.81117(7) 1.87074(19) 0.43809(11) 0.0249(5) Uani 1 1 d . . . . .
H30A H 0.8045 1.9545 0.4451 0.030 Uiso 1 1 calc R U . . .
H30B H 0.8064 1.8636 0.3909 0.030 Uiso 1 1 calc R U . . .
C31 C 0.77563(7) 1.7885(2) 0.44656(11) 0.0269(5) Uani 1 1 d . . . . .
H31A H 0.7797 1.7061 0.4339 0.032 Uiso 1 1 calc R U . . .
H31B H 0.7831 1.7879 0.4952 0.032 Uiso 1 1 calc R U . . .
C32 C 0.72404(7) 1.82628(18) 0.40336(11) 0.0236(5) Uani 1 1 d . . . . .
C33 C 0.70704(7) 1.93058(19) 0.41790(11) 0.0269(5) Uani 1 1 d . . . . .
C34 C 0.66090(8) 1.97205(19) 0.37844(12) 0.0292(5) Uani 1 1 d . . . . .
C35 C 0.62825(8) 1.9102(2) 0.32245(11) 0.0286(5) Uani 1 1 d . . . . .
H35A H 0.5964 1.9383 0.2956 0.034 Uiso 1 1 calc R U . . .
C36 C 0.64387(7) 1.80494(19) 0.30710(10) 0.0253(5) Uani 1 1 d . . . . .
C37 C 0.69091(7) 1.76462(19) 0.34614(11) 0.0236(5) Uani 1 1 d . . . . .
C40 C 0.65828(8) 1.6629(2) 0.24072(12) 0.0367(6) Uani 1 1 d . . . . .
H40A H 0.6495 1.5853 0.2165 0.044 Uiso 1 1 calc R U . . .
H40B H 0.6687 1.7188 0.2157 0.044 Uiso 1 1 calc R U . . .
C41 C 0.61720(8) 1.7148(2) 0.25095(11) 0.0308(5) Uani 1 1 d . . . . .
H41A H 0.5922 1.7535 0.2085 0.037 Uiso 1 1 calc R U . . .
C42 C 0.59648(8) 1.6137(2) 0.27553(11) 0.0301(5) Uani 1 1 d . . . . .
H42A H 0.5711 1.6465 0.2849 0.036 Uiso 1 1 calc R U . . .
H42B H 0.5815 1.5537 0.2387 0.036 Uiso 1 1 calc R U . . .
C43 C 0.68343(7) 1.5406(2) 0.34526(12) 0.0290(5) Uani 1 1 d . . . . .
H43A H 0.6846 1.4675 0.3210 0.035 Uiso 1 1 calc R U . . .
H43B H 0.7073 1.5319 0.3940 0.035 Uiso 1 1 calc R U . . .
C44 C 0.69654(8) 1.6484(2) 0.31537(11) 0.0293(5) Uani 1 1 d . . . . .
H44A H 0.7294 1.6404 0.3197 0.035 Uiso 1 1 calc R U . . .
C50 C 0.61470(8) 1.4340(2) 0.35065(12) 0.0326(5) Uani 1 1 d . . . . .
H50A H 0.5839 1.4512 0.3514 0.039 Uiso 1 1 calc R U . . .
C51 C 0.60399(10) 1.3438(2) 0.29425(14) 0.0488(7) Uani 1 1 d . . . . .
H51A H 0.5816 1.3789 0.2502 0.073 Uiso 1 1 calc R U . . .
H51B H 0.6338 1.3220 0.2937 0.073 Uiso 1 1 calc R U . . .
H51C H 0.5896 1.2723 0.3025 0.073 Uiso 1 1 calc R U . . .
C52 C 0.64924(9) 1.3828(2) 0.41977(12) 0.0378(6) Uani 1 1 d . . . . .
H52A H 0.6556 1.4425 0.4553 0.057 Uiso 1 1 calc R U . . .
H52B H 0.6351 1.3115 0.4287 0.057 Uiso 1 1 calc R U . . .
H52C H 0.6793 1.3612 0.4200 0.057 Uiso 1 1 calc R U . . .
C100 C 0.76285(14) 1.2526(3) 0.4078(2) 0.0693(10) Uani 1 1 d . . . . .
H10A H 0.7603 1.2039 0.4409 0.083 Uiso 1 1 calc R U . . .
C101 C 0.79405(12) 1.3458(3) 0.42713(17) 0.0665(9) Uani 1 1 d . . . . .
H10B H 0.8135 1.3621 0.4743 0.080 Uiso 1 1 calc R U . . .
C102 C 0.79782(9) 1.4169(3) 0.37942(14) 0.0476(7) Uani 1 1 d . . . . .
H10C H 0.8197 1.4819 0.3943 0.057 Uiso 1 1 calc R U . . .
C103 C 0.77056(9) 1.3960(2) 0.31052(14) 0.0428(6) Uani 1 1 d . . . . .
C105 C 0.73862(10) 1.3006(2) 0.29051(15) 0.0491(7) Uani 1 1 d . . . . .
H10D H 0.7193 1.2840 0.2433 0.059 Uiso 1 1 calc R U . . .
C106 C 0.73487(12) 1.2302(3) 0.33860(19) 0.0614(8) Uani 1 1 d . . . . .
H10E H 0.7129 1.1654 0.3243 0.074 Uiso 1 1 calc R U . . .
C107 C 0.77448(13) 1.4728(3) 0.25899(17) 0.0651(9) Uani 1 1 d . . . . .
H10F H 0.7524 1.4439 0.2131 0.098 Uiso 1 1 calc R U . . .
H10G H 0.7662 1.5552 0.2641 0.098 Uiso 1 1 calc R U . . .
H10H H 0.8074 1.4700 0.2657 0.098 Uiso 1 1 calc R U . . .
C90 C 0.5128(2) 1.1884(7) 0.3327(4) 0.085(2) Uani 0.5 1 d . . P A -1
H90A H 0.5131 1.1597 0.3746 0.128 Uiso 0.5 1 calc R U P A -1
H90B H 0.5441 1.2228 0.3436 0.128 Uiso 0.5 1 calc R U P A -1
H90C H 0.4879 1.2496 0.3115 0.128 Uiso 0.5 1 calc R U P A -1
C91 C 0.50188(11) 1.0815(3) 0.2819(2) 0.0732(10) Uani 1 1 d . . . . .
C92 C 0.50355(9) 0.9747(4) 0.31326(16) 0.0684(10) Uani 1 1 d . . . . .
H92A H 0.5061 0.9749 0.3577 0.082 Uiso 1 1 calc R U . . .
C93 C 0.50160(9) 0.8664(3) 0.28159(16) 0.0628(9) Uani 1 1 d . . . . .
H93A H 0.5025 0.7932 0.3038 0.075 Uiso 1 1 calc R U . . .


_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
B1 O1 1.501(3) . ?
B1 C30 1.629(3) . ?
B1 C1 1.666(3) . ?
B1 C7 1.670(3) . ?
N1 C43 1.514(3) . ?
N1 C42 1.514(3) . ?
N1 C50 1.532(3) . ?
N1 H1 0.93(2) . ?
O1 H2 0.79(2) . ?
F1 C2 1.355(3) . ?
F2 C3 1.347(3) . ?
F3 C4 1.347(3) . ?
F4 C5 1.341(3) . ?
F5 C6 1.362(3) . ?
F6 C8 1.357(3) . ?
F7 C9 1.352(3) . ?
F8 C10 1.344(2) . ?
F9 C11 1.345(3) . ?
F10 C12 1.353(2) . ?
F11 C34 1.356(2) . ?
F12 C33 1.358(2) . ?
C1 C6 1.375(3) . ?
C1 C2 1.396(3) . ?
C2 C3 1.373(3) . ?
C3 C4 1.367(4) . ?
C4 C5 1.377(4) . ?
C5 C6 1.382(3) . ?
C7 C12 1.379(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.379(3) . ?
C9 C10 1.373(3) . ?
C10 C11 1.364(3) . ?
C11 C12 1.379(3) . ?
C30 C31 1.531(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.512(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.385(3) . ?
C32 C37 1.391(3) . ?
C33 C34 1.382(3) . ?
C34 C35 1.372(3) . ?
C35 C36 1.381(3) . ?
C35 H35A 0.9500 . ?
C36 C37 1.398(3) . ?
C36 C41 1.514(3) . ?
C37 C44 1.518(3) . ?
C40 C44 1.532(3) . ?
C40 C41 1.534(3) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.531(3) . ?
C41 H41A 1.0000 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.525(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 1.0000 . ?
C50 C52 1.516(3) . ?
C50 C51 1.517(3) . ?
C50 H50A 1.0000 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C100 C101 1.359(5) . ?
C100 C106 1.388(5) . ?
C100 H10A 0.9500 . ?
C101 C102 1.374(4) . ?
C101 H10B 0.9500 . ?
C102 C103 1.377(4) . ?
C102 H10C 0.9500 . ?
C103 C105 1.391(4) . ?
C103 C107 1.482(4) . ?
C105 C106 1.377(4) . ?
C105 H10D 0.9500 . ?
C106 H10E 0.9500 . ?
C107 H10F 0.9800 . ?
C107 H10G 0.9800 . ?
C107 H10H 0.9800 . ?
C90 C91 1.567(7) . ?
C90 H90A 0.9800 . ?
C90 H90B 0.9800 . ?
C90 H90C 0.9800 . ?
C91 C91 1.364(7) 2_655 ?
C91 C92 1.372(5) . ?
C92 C93 1.388(5) . ?
C92 H92A 0.9500 . ?
C93 C93 1.358(6) 2_655 ?
C93 H93A 0.9500 . ?

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
O1 B1 C30 108.20(16) . . ?
O1 B1 C1 112.76(18) . . ?
C30 B1 C1 110.37(17) . . ?
O1 B1 C7 106.92(17) . . ?
C30 B1 C7 113.40(18) . . ?
C1 B1 C7 105.21(15) . . ?
C43 N1 C42 116.36(17) . . ?
C43 N1 C50 112.42(16) . . ?
C42 N1 C50 110.38(16) . . ?
C43 N1 H1 108.5(13) . . ?
C42 N1 H1 104.9(14) . . ?
C50 N1 H1 103.1(13) . . ?
B1 O1 H2 112.4(17) . . ?
C6 C1 C2 112.5(2) . . ?
C6 C1 B1 127.19(19) . . ?
C2 C1 B1 120.31(19) . . ?
F1 C2 C3 115.6(2) . . ?
F1 C2 C1 119.8(2) . . ?
C3 C2 C1 124.6(2) . . ?
F2 C3 C4 119.6(2) . . ?
F2 C3 C2 120.7(2) . . ?
C4 C3 C2 119.7(2) . . ?
F3 C4 C3 120.5(2) . . ?
F3 C4 C5 120.4(2) . . ?
C3 C4 C5 119.1(2) . . ?
F4 C5 C4 120.6(2) . . ?
F4 C5 C6 120.8(2) . . ?
C4 C5 C6 118.6(2) . . ?
F5 C6 C1 120.09(19) . . ?
F5 C6 C5 114.4(2) . . ?
C1 C6 C5 125.5(2) . . ?
C12 C7 C8 112.95(19) . . ?
C12 C7 B1 126.30(18) . . ?
C8 C7 B1 120.76(19) . . ?
F6 C8 C9 115.60(19) . . ?
F6 C8 C7 120.17(19) . . ?
C9 C8 C7 124.2(2) . . ?
F7 C9 C10 119.7(2) . . ?
F7 C9 C8 120.6(2) . . ?
C10 C9 C8 119.7(2) . . ?
F8 C10 C11 120.9(2) . . ?
F8 C10 C9 120.4(2) . . ?
C11 C10 C9 118.7(2) . . ?
F9 C11 C10 119.8(2) . . ?
F9 C11 C12 120.5(2) . . ?
C10 C11 C12 119.7(2) . . ?
F10 C12 C7 120.67(18) . . ?
F10 C12 C11 114.58(19) . . ?
C7 C12 C11 124.7(2) . . ?
C31 C30 B1 112.55(17) . . ?
C31 C30 H30A 109.1 . . ?
B1 C30 H30A 109.1 . . ?
C31 C30 H30B 109.1 . . ?
B1 C30 H30B 109.1 . . ?
H30A C30 H30B 107.8 . . ?
C32 C31 C30 112.89(17) . . ?
C32 C31 H31A 109.0 . . ?
C30 C31 H31A 109.0 . . ?
C32 C31 H31B 109.0 . . ?
C30 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C33 C32 C37 115.02(18) . . ?
C33 C32 C31 120.59(19) . . ?
C37 C32 C31 124.35(19) . . ?
F12 C33 C34 117.46(19) . . ?
F12 C33 C32 119.49(18) . . ?
C34 C33 C32 123.0(2) . . ?
F11 C34 C35 120.26(19) . . ?
F11 C34 C33 118.1(2) . . ?
C35 C34 C33 121.6(2) . . ?
C34 C35 C36 116.75(19) . . ?
C34 C35 H35A 121.6 . . ?
C36 C35 H35A 121.6 . . ?
C35 C36 C37 121.5(2) . . ?
C35 C36 C41 130.25(19) . . ?
C37 C36 C41 108.25(18) . . ?
C32 C37 C36 122.02(19) . . ?
C32 C37 C44 129.69(19) . . ?
C36 C37 C44 108.28(18) . . ?
C44 C40 C41 99.95(17) . . ?
C44 C40 H40A 111.8 . . ?
C41 C40 H40A 111.8 . . ?
C44 C40 H40B 111.8 . . ?
C41 C40 H40B 111.8 . . ?
H40A C40 H40B 109.5 . . ?
C36 C41 C42 111.44(18) . . ?
C36 C41 C40 101.06(18) . . ?
C42 C41 C40 107.83(19) . . ?
C36 C41 H41A 112.0 . . ?
C42 C41 H41A 112.0 . . ?
C40 C41 H41A 112.0 . . ?
N1 C42 C41 112.85(17) . . ?
N1 C42 H42A 109.0 . . ?
C41 C42 H42A 109.0 . . ?
N1 C42 H42B 109.0 . . ?
C41 C42 H42B 109.0 . . ?
H42A C42 H42B 107.8 . . ?
N1 C43 C44 111.83(17) . . ?
N1 C43 H43A 109.2 . . ?
C44 C43 H43A 109.2 . . ?
N1 C43 H43B 109.2 . . ?
C44 C43 H43B 109.2 . . ?
H43A C43 H43B 107.9 . . ?
C37 C44 C43 111.65(17) . . ?
C37 C44 C40 101.29(18) . . ?
C43 C44 C40 108.42(18) . . ?
C37 C44 H44A 111.7 . . ?
C43 C44 H44A 111.7 . . ?
C40 C44 H44A 111.7 . . ?
C52 C50 C51 111.0(2) . . ?
C52 C50 N1 110.01(18) . . ?
C51 C50 N1 113.22(19) . . ?
C52 C50 H50A 107.5 . . ?
C51 C50 H50A 107.5 . . ?
N1 C50 H50A 107.5 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C50 C52 H52A 109.5 . . ?
C50 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C50 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C101 C100 C106 118.6(3) . . ?
C101 C100 H10A 120.7 . . ?
C106 C100 H10A 120.7 . . ?
C100 C101 C102 121.0(3) . . ?
C100 C101 H10B 119.5 . . ?
C102 C101 H10B 119.5 . . ?
C101 C102 C103 121.4(3) . . ?
C101 C102 H10C 119.3 . . ?
C103 C102 H10C 119.3 . . ?
C102 C103 C105 117.8(3) . . ?
C102 C103 C107 121.5(3) . . ?
C105 C103 C107 120.7(3) . . ?
C106 C105 C103 120.5(3) . . ?
C106 C105 H10D 119.8 . . ?
C103 C105 H10D 119.8 . . ?
C105 C106 C100 120.7(3) . . ?
C105 C106 H10E 119.6 . . ?
C100 C106 H10E 119.6 . . ?
C103 C107 H10F 109.5 . . ?
C103 C107 H10G 109.5 . . ?
H10F C107 H10G 109.5 . . ?
C103 C107 H10H 109.5 . . ?
H10F C107 H10H 109.5 . . ?
H10G C107 H10H 109.5 . . ?
C91 C90 H90A 109.5 . . ?
C91 C90 H90B 109.5 . . ?
H90A C90 H90B 109.5 . . ?
C91 C90 H90C 109.5 . . ?
H90A C90 H90C 109.5 . . ?
H90B C90 H90C 109.5 . . ?
C91 C91 C92 119.4(2) 2_655 . ?
C91 C91 C90 129.0(3) 2_655 . ?
C92 C91 C90 111.0(4) . . ?
C91 C92 C93 121.5(3) . . ?
C91 C92 H92A 119.2 . . ?
C93 C92 H92A 119.2 . . ?
C93 C93 C92 119.1(2) 2_655 . ?
C93 C93 H93A 120.4 2_655 . ?
C92 C93 H93A 120.4 . . ?

_refine_diff_density_max         0.379
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.049

