# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_RM1838e
_database_code_depnum_ccdc_archive 'CCDC 1897205'
loop_
_audit_author_name
_audit_author_address
'Theo Gazis'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-14 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_RM1838e             
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         13 Note
RESPONSE: A small number of low angle reflections were obscured by the beamstop. Nevertheless this provided 99.8% of data to 25.4 degrees in theta and additional data were collected up to 29.65 degrees affording a final data:parameter ratio of 6315:388 which was more than adequate for refinement. 
;
_vrf_PLAT420_RM1838e             
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check
RESPONSE: N-H group sterically hindered by BAr3 group
;
_vrf_PLAT420_RM1838e_2           
;
PROBLEM: D-H Without Acceptor       N1       --H1B      .     Please Check
RESPONSE: N-H group sterically hindered by BAr3 group
;
# Added during the CSD deposition process: Thursday 14 February 2019 09:22 AM
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H18 B F9 N2'
_chemical_formula_sum            'C31 H18 B F9 N2'
_chemical_formula_weight         600.28

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'

_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                   9.7975(7)
_cell_length_b                   10.9639(11)
_cell_length_c                   13.8619(15)
_cell_angle_alpha                106.193(9)
_cell_angle_beta                 102.430(7)
_cell_angle_gamma                105.643(7)
_cell_volume                     1307.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2666
_cell_measurement_theta_min      4.019
_cell_measurement_theta_max      28.268

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration 
over a multifaceted crystal model. Empirical absorption 
correction using spherical harmonics, implemented in SCALE3 
ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'SuperNova Dual Atlas'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10154
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.311
_diffrn_reflns_theta_max         29.739
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6080
_reflns_number_gt                3970
_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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    Mercury
_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)+(0.0488P)²+0.4765P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         6080
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1486
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
B1 B 0.4228(3) 0.4633(3) 0.1762(2) 0.0271(6) Uani 1 1 d . . . . .
N1 N 0.3651(2) 0.4624(2) 0.28297(16) 0.0256(4) Uani 1 1 d . . . . .
H1A H 0.287(3) 0.493(3) 0.280(2) 0.031 Uiso 1 1 d . U . . .
H1B H 0.331(3) 0.378(3) 0.282(2) 0.031 Uiso 1 1 d . U . . .
C1 C 0.4708(2) 0.6397(2) 0.44747(19) 0.0248(5) Uani 1 1 d . . . . .
N2 N 0.4844(2) 0.53733(19) 0.38251(16) 0.0258(4) Uani 1 1 d . . . . .
C11 C 0.5208(2) 0.3649(2) 0.1626(2) 0.0260(5) Uani 1 1 d . . . . .
C12 C 0.6378(3) 0.3758(2) 0.2471(2) 0.0285(5) Uani 1 1 d . . . . .
H12 H 0.656485 0.437960 0.315924 0.034 Uiso 1 1 calc R U . . .
C13 C 0.7258(3) 0.2978(2) 0.2320(2) 0.0300(5) Uani 1 1 d . . . . .
F13 F 0.83962(16) 0.31062(15) 0.31441(13) 0.0428(4) Uani 1 1 d . . . . .
C14 C 0.7030(3) 0.2058(3) 0.1342(2) 0.0349(6) Uani 1 1 d . . . . .
F14 F 0.7898(2) 0.13037(18) 0.11981(14) 0.0528(5) Uani 1 1 d . . . . .
C15 C 0.5887(3) 0.1945(3) 0.0504(2) 0.0364(6) Uani 1 1 d . . . . .
F15 F 0.5653(2) 0.10358(17) -0.04650(13) 0.0550(5) Uani 1 1 d . . . . .
C16 C 0.4988(3) 0.2712(2) 0.0627(2) 0.0310(6) Uani 1 1 d . . . . .
H16 H 0.421187 0.260649 0.003169 0.037 Uiso 1 1 calc R U . . .
C21 C 0.5179(2) 0.6211(2) 0.20465(18) 0.0244(5) Uani 1 1 d . . . . .
C22 C 0.6709(3) 0.6679(2) 0.21540(19) 0.0276(5) Uani 1 1 d . . . . .
H22 H 0.721008 0.604864 0.202571 0.033 Uiso 1 1 calc R U . . .
C23 C 0.7488(3) 0.8042(3) 0.2443(2) 0.0301(5) Uani 1 1 d . . . . .
F23 F 0.89637(15) 0.84914(15) 0.25516(13) 0.0423(4) Uani 1 1 d . . . . .
C24 C 0.6818(3) 0.8992(2) 0.2651(2) 0.0305(6) Uani 1 1 d . . . . .
F24 F 0.75915(17) 1.03222(14) 0.29486(13) 0.0431(4) Uani 1 1 d . . . . .
C25 C 0.5317(3) 0.8540(2) 0.2542(2) 0.0297(5) Uani 1 1 d . . . . .
F25 F 0.46604(17) 0.94822(14) 0.27498(13) 0.0416(4) Uani 1 1 d . . . . .
C26 C 0.4506(3) 0.7192(2) 0.22435(19) 0.0281(5) Uani 1 1 d . . . . .
H26 H 0.347112 0.691718 0.216868 0.034 Uiso 1 1 calc R U . . .
C31 C 0.2659(2) 0.4039(2) 0.08102(19) 0.0266(5) Uani 1 1 d . . . . .
C32 C 0.1623(3) 0.2749(2) 0.0595(2) 0.0305(5) Uani 1 1 d . . . . .
H32 H 0.184458 0.223508 0.101780 0.037 Uiso 1 1 calc R U . . .
C33 C 0.0296(3) 0.2218(3) -0.0215(2) 0.0337(6) Uani 1 1 d . . . . .
F33 F -0.06785(16) 0.09625(16) -0.04264(13) 0.0470(4) Uani 1 1 d . . . . .
C34 C -0.0061(3) 0.2918(3) -0.0857(2) 0.0346(6) Uani 1 1 d . . . . .
F34 F -0.13541(16) 0.23599(18) -0.16683(13) 0.0501(4) Uani 1 1 d . . . . .
C35 C 0.0939(3) 0.4168(3) -0.0666(2) 0.0346(6) Uani 1 1 d . . . . .
F35 F 0.05950(18) 0.48399(17) -0.13211(13) 0.0502(4) Uani 1 1 d . . . . .
C36 C 0.2277(3) 0.4731(3) 0.0143(2) 0.0295(5) Uani 1 1 d . . . . .
H36 H 0.294947 0.559898 0.024904 0.035 Uiso 1 1 calc R U . . .
C41 C 0.6059(2) 0.7233(2) 0.54099(19) 0.0254(5) Uani 1 1 d . . . . .
C42 C 0.5944(3) 0.7979(2) 0.63626(19) 0.0268(5) Uani 1 1 d . . . . .
H42 H 0.499423 0.798501 0.641303 0.032 Uiso 1 1 calc R U . . .
C43 C 0.7209(3) 0.8714(2) 0.7241(2) 0.0293(5) Uani 1 1 d . . . . .
H43 H 0.711756 0.921872 0.788782 0.035 Uiso 1 1 calc R U . . .
C44 C 0.8603(3) 0.8717(2) 0.7179(2) 0.0327(6) Uani 1 1 d . . . . .
H44 H 0.946358 0.920663 0.778374 0.039 Uiso 1 1 calc R U . . .
C45 C 0.8732(3) 0.7997(3) 0.6225(2) 0.0345(6) Uani 1 1 d . . . . .
H45 H 0.968706 0.800697 0.617509 0.041 Uiso 1 1 calc R U . . .
C46 C 0.7480(3) 0.7267(2) 0.5347(2) 0.0303(5) Uani 1 1 d . . . . .
H46 H 0.758153 0.678462 0.469738 0.036 Uiso 1 1 calc R U . . .
C51 C 0.3372(2) 0.6814(2) 0.43810(18) 0.0252(5) Uani 1 1 d . . . . .
C52 C 0.1983(3) 0.5927(3) 0.4272(2) 0.0331(6) Uani 1 1 d . . . . .
H52 H 0.186989 0.502652 0.423852 0.040 Uiso 1 1 calc R U . . .
C53 C 0.0761(3) 0.6345(3) 0.4211(2) 0.0398(7) Uani 1 1 d . . . . .
H53 H -0.017957 0.573469 0.414463 0.048 Uiso 1 1 calc R U . . .
C54 C 0.0911(3) 0.7642(3) 0.4247(2) 0.0431(7) Uani 1 1 d . . . . .
H54 H 0.007075 0.792324 0.419607 0.052 Uiso 1 1 calc R U . . .
C55 C 0.2292(3) 0.8542(3) 0.4359(2) 0.0395(6) Uani 1 1 d . . . . .
H55 H 0.239580 0.943867 0.438505 0.047 Uiso 1 1 calc R U . . .
C56 C 0.3510(3) 0.8131(2) 0.4431(2) 0.0320(6) Uani 1 1 d . . . . .
H56 H 0.445395 0.875295 0.451558 0.038 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 C21 1.615(3) . ?
B1 C31 1.623(4) . ?
B1 C11 1.626(4) . ?
B1 N1 1.696(3) . ?
N1 N2 1.450(3) . ?
N1 H1A 0.91(3) . ?
N1 H1B 0.89(3) . ?
C1 N2 1.287(3) . ?
C1 C41 1.489(3) . ?
C1 C51 1.491(3) . ?
C11 C12 1.403(3) . ?
C11 C16 1.407(3) . ?
C12 C13 1.376(3) . ?
C12 H12 0.9500 . ?
C13 F13 1.359(3) . ?
C13 C14 1.376(4) . ?
C14 F14 1.344(3) . ?
C14 C15 1.379(4) . ?
C15 F15 1.359(3) . ?
C15 C16 1.377(4) . ?
C16 H16 0.9500 . ?
C21 C26 1.401(3) . ?
C21 C22 1.407(3) . ?
C22 C23 1.376(3) . ?
C22 H22 0.9500 . ?
C23 F23 1.355(3) . ?
C23 C24 1.371(3) . ?
C24 F24 1.344(3) . ?
C24 C25 1.379(3) . ?
C25 F25 1.355(3) . ?
C25 C26 1.368(3) . ?
C26 H26 0.9500 . ?
C31 C36 1.403(3) . ?
C31 C32 1.407(3) . ?
C32 C33 1.374(3) . ?
C32 H32 0.9500 . ?
C33 F33 1.356(3) . ?
C33 C34 1.377(4) . ?
C34 F34 1.353(3) . ?
C34 C35 1.367(4) . ?
C35 F35 1.363(3) . ?
C35 C36 1.379(3) . ?
C36 H36 0.9500 . ?
C41 C42 1.392(3) . ?
C41 C46 1.405(3) . ?
C42 C43 1.390(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.386(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.390(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.382(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C52 1.392(3) . ?
C51 C56 1.394(3) . ?
C52 C53 1.386(4) . ?
C52 H52 0.9500 . ?
C53 C54 1.375(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.390(4) . ?
C54 H54 0.9500 . ?
C55 C56 1.378(4) . ?
C55 H55 0.9500 . ?
C56 H56 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
C21 B1 C31 114.7(2) . . ?
C21 B1 C11 113.71(19) . . ?
C31 B1 C11 112.9(2) . . ?
C21 B1 N1 103.85(19) . . ?
C31 B1 N1 102.30(18) . . ?
C11 B1 N1 108.08(19) . . ?
N2 N1 B1 113.03(17) . . ?
N2 N1 H1A 111.7(17) . . ?
B1 N1 H1A 109.6(16) . . ?
N2 N1 H1B 105.8(17) . . ?
B1 N1 H1B 110.0(17) . . ?
H1A N1 H1B 106(2) . . ?
N2 C1 C41 114.6(2) . . ?
N2 C1 C51 127.2(2) . . ?
C41 C1 C51 118.3(2) . . ?
C1 N2 N1 117.42(19) . . ?
C12 C11 C16 116.8(2) . . ?
C12 C11 B1 122.2(2) . . ?
C16 C11 B1 120.8(2) . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
F13 C13 C12 120.4(2) . . ?
F13 C13 C14 117.8(2) . . ?
C12 C13 C14 121.8(2) . . ?
F14 C14 C13 121.5(2) . . ?
F14 C14 C15 120.8(2) . . ?
C13 C14 C15 117.7(2) . . ?
F15 C15 C16 119.9(2) . . ?
F15 C15 C14 118.0(2) . . ?
C16 C15 C14 122.0(2) . . ?
C15 C16 C11 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C26 C21 C22 116.8(2) . . ?
C26 C21 B1 120.3(2) . . ?
C22 C21 B1 122.8(2) . . ?
C23 C22 C21 120.7(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
F23 C23 C24 117.7(2) . . ?
F23 C23 C22 120.6(2) . . ?
C24 C23 C22 121.8(2) . . ?
F24 C24 C23 121.4(2) . . ?
F24 C24 C25 120.7(2) . . ?
C23 C24 C25 117.9(2) . . ?
F25 C25 C26 120.5(2) . . ?
F25 C25 C24 117.7(2) . . ?
C26 C25 C24 121.8(2) . . ?
C25 C26 C21 121.0(2) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
C36 C31 C32 116.5(2) . . ?
C36 C31 B1 123.3(2) . . ?
C32 C31 B1 120.2(2) . . ?
C33 C32 C31 121.2(2) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
F33 C33 C32 120.6(2) . . ?
F33 C33 C34 118.0(2) . . ?
C32 C33 C34 121.3(2) . . ?
F34 C34 C35 121.4(2) . . ?
F34 C34 C33 120.3(2) . . ?
C35 C34 C33 118.2(2) . . ?
F35 C35 C34 117.9(2) . . ?
F35 C35 C36 120.2(2) . . ?
C34 C35 C36 121.9(2) . . ?
C35 C36 C31 120.8(2) . . ?
C35 C36 H36 119.6 . . ?
C31 C36 H36 119.6 . . ?
C42 C41 C46 118.7(2) . . ?
C42 C41 C1 121.1(2) . . ?
C46 C41 C1 120.2(2) . . ?
C43 C42 C41 120.5(2) . . ?
C43 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C44 C43 C42 120.4(2) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C43 C44 C45 119.5(2) . . ?
C43 C44 H44 120.3 . . ?
C45 C44 H44 120.3 . . ?
C46 C45 C44 120.4(2) . . ?
C46 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C45 C46 C41 120.5(2) . . ?
C45 C46 H46 119.8 . . ?
C41 C46 H46 119.8 . . ?
C52 C51 C56 118.6(2) . . ?
C52 C51 C1 121.5(2) . . ?
C56 C51 C1 119.8(2) . . ?
C53 C52 C51 120.6(2) . . ?
C53 C52 H52 119.7 . . ?
C51 C52 H52 119.7 . . ?
C54 C53 C52 120.1(2) . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C53 C54 C55 120.1(2) . . ?
C53 C54 H54 120.0 . . ?
C55 C54 H54 120.0 . . ?
C56 C55 C54 119.9(2) . . ?
C56 C55 H55 120.1 . . ?
C54 C55 H55 120.1 . . ?
C55 C56 C51 120.8(2) . . ?
C55 C56 H56 119.6 . . ?
C51 C56 H56 119.6 . . ?

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.059


_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_rm1848h
_database_code_depnum_ccdc_archive 'CCDC 1897207'
loop_
_audit_author_name
_audit_author_address
'Theo Gazis'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-14 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_rm1848h             
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         14 Note
RESPONSE: A small number of low angle reflections were obscured by the beamstop.
;
# Added during the CSD deposition process: Thursday 14 February 2019 09:22 AM
# end Validation Reply Form

# start Validation Reply Form
_vrf_PLAT260_rm1848h             
;
PROBLEM: Large Average Ueq of Residue Including       Cl1      0.121 Check
RESPONSE: Disordered CH2Cl2 molecule refined over two sites via a pivot about Cl1.
;
_vrf_PLAT340_rm1848h             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00503 Ang.
RESPONSE: weakly diffraxcting crystal with I/sigma
;
# end Validation Reply Form 
_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H30 B2 F18 N4, 2 (C H2 Cl2)'
_chemical_formula_sum            'C58 H34 B2 Cl4 F18 N4'
_chemical_formula_weight         1292.31

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'
O O 0.0106 0.0060 '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'
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                   9.4053(6)
_cell_length_b                   11.2224(7)
_cell_length_c                   13.6936(8)
_cell_angle_alpha                103.791(5)
_cell_angle_beta                 98.886(5)
_cell_angle_gamma                90.099(5)
_cell_volume                     1385.73(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2576
_cell_measurement_theta_min      4.0640
_cell_measurement_theta_max      26.8390

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             650
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.319
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration
over a multifaceted crystal model. Empirical absorption 
correction using spherical harmonics, implemented in SCALE3 
ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.882
_oxdiff_exptl_absorpt_empirical_full_max 1.371
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10704
_diffrn_reflns_av_unetI/netI     0.0860
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.504
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             6091
_reflns_number_gt                3327
_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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Mercury CCDC'
_computing_publication_material  ?
_refine_special_details          
;
Structure solved by direct methods with half a molecule and a CH2Cl2
solvent molecule in the asymmetric unit. The CH2Cl2 was disordered by a
pivot mechanism around cl1. Disorder refined with common Uij for two
components of C1s and Cl2 in DCM. Loose DFIX command used for C-Cl bonds.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+1.1033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6091
_refine_ls_number_parameters     393
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.031
_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
C11 C -0.1609(3) 0.9961(3) 0.2184(2) 0.0303(8) Uani 1 1 d . . . . .
C16 C -0.2159(3) 1.0933(3) 0.2835(3) 0.0345(8) Uani 1 1 d . . . . .
C12 C -0.1636(4) 1.0203(4) 0.1234(3) 0.0421(9) Uani 1 1 d . . . . .
C15 C -0.2726(4) 1.1979(4) 0.2595(3) 0.0448(9) Uani 1 1 d . . . . .
H15 H -0.309527 1.258163 0.307191 0.054 Uiso 1 1 calc R U . . .
C14 C -0.2718(4) 1.2087(4) 0.1626(3) 0.0509(10) Uani 1 1 d . . . . .
C13 C -0.2167(4) 1.1212(4) 0.0917(3) 0.0516(11) Uani 1 1 d . . . . .
H13 H -0.215340 1.129672 0.025873 0.062 Uiso 1 1 calc R U . . .
F12 F -0.1078(2) 0.9337(2) 0.05266(16) 0.0593(6) Uani 1 1 d . . . . .
F14 F -0.3279(3) 1.3098(2) 0.1350(2) 0.0768(8) Uani 1 1 d . . . . .
F16 F -0.2171(2) 1.08851(19) 0.38276(15) 0.0454(5) Uani 1 1 d . . . . .
B1 B -0.0938(4) 0.8708(4) 0.2432(3) 0.0281(8) Uani 1 1 d . . . . .
C21 C 0.0824(3) 0.8877(3) 0.2639(2) 0.0290(7) Uani 1 1 d . . . . .
C22 C 0.1717(3) 0.8450(3) 0.1916(2) 0.0335(8) Uani 1 1 d . . . . .
C26 C 0.1619(3) 0.9521(3) 0.3548(2) 0.0327(8) Uani 1 1 d . . . . .
C25 C 0.3083(3) 0.9696(3) 0.3784(3) 0.0404(9) Uani 1 1 d . . . . .
H25 H 0.353385 1.011936 0.442655 0.048 Uiso 1 1 calc R U . . .
C23 C 0.3201(3) 0.8589(3) 0.2067(3) 0.0407(9) Uani 1 1 d . . . . .
H23 H 0.373300 0.827794 0.155026 0.049 Uiso 1 1 calc R U . . .
C24 C 0.3845(3) 0.9209(4) 0.3018(3) 0.0424(9) Uani 1 1 d . . . . .
F22 F 0.11024(19) 0.7837(2) 0.09651(14) 0.0439(5) Uani 1 1 d . . . . .
F24 F 0.53105(19) 0.9342(2) 0.32157(18) 0.0603(7) Uani 1 1 d . . . . .
F26 F 0.08701(19) 1.00700(19) 0.43138(14) 0.0428(5) Uani 1 1 d . . . . .
C31 C -0.1563(3) 0.7430(3) 0.1610(2) 0.0299(8) Uani 1 1 d . . . . .
C36 C -0.2885(3) 0.7301(3) 0.0966(3) 0.0349(8) Uani 1 1 d . . . . .
C33 C -0.1355(4) 0.5217(3) 0.0822(3) 0.0399(9) Uani 1 1 d . . . . .
H33 H -0.083385 0.450891 0.078482 0.048 Uiso 1 1 calc R U . . .
C32 C -0.0871(3) 0.6311(3) 0.1499(2) 0.0354(8) Uani 1 1 d . . . . .
C35 C -0.3448(4) 0.6246(4) 0.0254(3) 0.0401(9) Uani 1 1 d . . . . .
H35 H -0.432568 0.623289 -0.016824 0.048 Uiso 1 1 calc R U . . .
C34 C -0.2648(4) 0.5231(4) 0.0204(3) 0.0421(9) Uani 1 1 d . . . . .
F32 F 0.04012(19) 0.62709(19) 0.21114(15) 0.0454(5) Uani 1 1 d . . . . .
F34 F -0.3160(2) 0.4169(2) -0.04792(16) 0.0589(7) Uani 1 1 d . . . . .
F36 F -0.37311(19) 0.8292(2) 0.10199(16) 0.0470(5) Uani 1 1 d . . . . .
N1 N -0.0741(3) 0.7631(3) 0.39145(19) 0.0295(6) Uani 1 1 d . . . . .
N2 N -0.1482(3) 0.8551(2) 0.34826(19) 0.0291(6) Uani 1 1 d . . . . .
H2A H -0.135304 0.926791 0.394130 0.035 Uiso 1 1 calc R U . . .
H2B H -0.242070 0.835507 0.334765 0.035 Uiso 1 1 calc R U . . .
C41 C -0.3143(3) 0.6687(3) 0.3907(2) 0.0298(7) Uani 1 1 d . . . . .
C46 C -0.3891(4) 0.7141(4) 0.4703(3) 0.0454(10) Uani 1 1 d . . . . .
H46 H -0.339350 0.754562 0.533767 0.054 Uiso 1 1 calc R U . . .
C45 C -0.5370(4) 0.6996(4) 0.4559(3) 0.0570(12) Uani 1 1 d . . . . .
H45 H -0.586994 0.732250 0.509031 0.068 Uiso 1 1 calc R U . . .
C44 C -0.6108(4) 0.6369(4) 0.3631(4) 0.0614(13) Uani 1 1 d . . . . .
H44 H -0.710528 0.626243 0.353736 0.074 Uiso 1 1 calc R U . . .
C42 C -0.3885(4) 0.6058(4) 0.2974(3) 0.0446(10) Uani 1 1 d . . . . .
H42 H -0.339048 0.574247 0.243740 0.054 Uiso 1 1 calc R U . . .
C43 C -0.5371(4) 0.5901(4) 0.2843(3) 0.0612(13) Uani 1 1 d . . . . .
H43 H -0.587161 0.547476 0.221642 0.073 Uiso 1 1 calc R U . . .
C47 C -0.1531(3) 0.6788(3) 0.4095(2) 0.0271(7) Uani 1 1 d . . . . .
C48 C -0.0740(3) 0.5871(3) 0.4560(2) 0.0291(7) Uani 1 1 d . . . . .
C49 C 0.0727(3) 0.6039(3) 0.4921(3) 0.0385(9) Uani 1 1 d . . . . .
H49 H 0.121971 0.673744 0.487348 0.046 Uiso 1 1 calc R U . . .
C50 C -0.1457(3) 0.4824(3) 0.4650(3) 0.0388(9) Uani 1 1 d . . . . .
H50 H -0.244198 0.470564 0.441834 0.047 Uiso 1 1 calc R U . . .
Cl1 Cl 0.35604(17) 0.20051(19) 0.19610(16) 0.1244(7) Uani 1 1 d D . . . .
C1SA C 0.1744(6) 0.2135(7) 0.1802(5) 0.120(3) Uani 0.654(18) 1 d D . P A 1
H1S1 H 0.130624 0.138350 0.187265 0.144 Uiso 0.654(18) 1 calc R U P A 1
H1S2 H 0.141697 0.221030 0.111295 0.144 Uiso 0.654(18) 1 calc R U P A 1
Cl2A Cl 0.1116(8) 0.3394(11) 0.2662(6) 0.121(2) Uani 0.654(18) 1 d D . P A 1
C1SB C 0.1744(6) 0.2135(7) 0.1802(5) 0.120(3) Uani 0.346(18) 1 d D . P A 2
H1S3 H 0.146571 0.254386 0.125636 0.144 Uiso 0.346(18) 1 calc R U P A 2
H1S4 H 0.129344 0.131710 0.158794 0.144 Uiso 0.346(18) 1 calc R U P A 2
Cl2B Cl 0.1134(16) 0.2861(14) 0.2777(12) 0.121(2) Uani 0.346(18) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 C12 1.387(5) . ?
C11 C16 1.391(5) . ?
C11 B1 1.630(5) . ?
C16 F16 1.375(4) . ?
C16 C15 1.379(5) . ?
C12 F12 1.367(4) . ?
C12 C13 1.375(5) . ?
C15 C14 1.362(5) . ?
C15 H15 0.9300 . ?
C14 F14 1.361(4) . ?
C14 C13 1.370(6) . ?
C13 H13 0.9300 . ?
B1 C21 1.640(4) . ?
B1 C31 1.641(5) . ?
B1 N2 1.647(4) . ?
C21 C26 1.382(4) . ?
C21 C22 1.395(4) . ?
C22 F22 1.357(4) . ?
C22 C23 1.382(4) . ?
C26 C25 1.368(4) . ?
C26 F26 1.378(4) . ?
C25 C24 1.368(5) . ?
C25 H25 0.9300 . ?
C23 C24 1.367(5) . ?
C23 H23 0.9300 . ?
C24 F24 1.364(4) . ?
C31 C36 1.394(4) . ?
C31 C32 1.402(5) . ?
C36 F36 1.362(4) . ?
C36 C35 1.386(5) . ?
C33 C34 1.372(5) . ?
C33 C32 1.378(5) . ?
C33 H33 0.9300 . ?
C32 F32 1.358(4) . ?
C35 C34 1.360(5) . ?
C35 H35 0.9300 . ?
C34 F34 1.362(4) . ?
N1 C47 1.294(4) . ?
N1 N2 1.437(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
C41 C42 1.381(5) . ?
C41 C46 1.385(5) . ?
C41 C47 1.497(4) . ?
C46 C45 1.378(5) . ?
C46 H46 0.9300 . ?
C45 C44 1.375(6) . ?
C45 H45 0.9300 . ?
C44 C43 1.372(6) . ?
C44 H44 0.9300 . ?
C42 C43 1.387(5) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C47 C48 1.479(4) . ?
C48 C49 1.389(4) . ?
C48 C50 1.394(4) . ?
C49 C50 1.380(5) 2_566 ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
Cl1 C1SB 1.699(5) . ?
Cl1 C1SA 1.699(5) . ?
C1SA Cl2A 1.776(10) . ?
C1SA H1S1 0.9700 . ?
C1SA H1S2 0.9700 . ?
C1SB Cl2B 1.580(15) . ?
C1SB H1S3 0.9700 . ?
C1SB H1S4 0.9700 . ?

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
C12 C11 C16 110.3(3) . . ?
C12 C11 B1 121.2(3) . . ?
C16 C11 B1 128.4(3) . . ?
F16 C16 C15 114.2(3) . . ?
F16 C16 C11 119.0(3) . . ?
C15 C16 C11 126.8(3) . . ?
F12 C12 C13 116.0(3) . . ?
F12 C12 C11 116.5(3) . . ?
C13 C12 C11 127.5(4) . . ?
C14 C15 C16 116.8(4) . . ?
C14 C15 H15 121.6 . . ?
C16 C15 H15 121.6 . . ?
F14 C14 C15 118.9(4) . . ?
F14 C14 C13 118.7(4) . . ?
C15 C14 C13 122.4(4) . . ?
C14 C13 C12 116.1(4) . . ?
C14 C13 H13 121.9 . . ?
C12 C13 H13 121.9 . . ?
C11 B1 C21 108.5(3) . . ?
C11 B1 C31 115.3(3) . . ?
C21 B1 C31 114.1(3) . . ?
C11 B1 N2 107.3(2) . . ?
C21 B1 N2 108.8(2) . . ?
C31 B1 N2 102.4(2) . . ?
C26 C21 C22 110.8(3) . . ?
C26 C21 B1 124.1(3) . . ?
C22 C21 B1 125.1(3) . . ?
F22 C22 C23 115.2(3) . . ?
F22 C22 C21 118.5(3) . . ?
C23 C22 C21 126.3(3) . . ?
C25 C26 F26 115.0(3) . . ?
C25 C26 C21 127.7(3) . . ?
F26 C26 C21 117.3(3) . . ?
C24 C25 C26 116.0(3) . . ?
C24 C25 H25 122.0 . . ?
C26 C25 H25 122.0 . . ?
C24 C23 C22 116.3(3) . . ?
C24 C23 H23 121.8 . . ?
C22 C23 H23 121.8 . . ?
F24 C24 C25 118.5(3) . . ?
F24 C24 C23 118.7(3) . . ?
C25 C24 C23 122.8(3) . . ?
C36 C31 C32 111.2(3) . . ?
C36 C31 B1 124.4(3) . . ?
C32 C31 B1 124.4(3) . . ?
F36 C36 C35 115.1(3) . . ?
F36 C36 C31 118.6(3) . . ?
C35 C36 C31 126.3(3) . . ?
C34 C33 C32 116.3(4) . . ?
C34 C33 H33 121.8 . . ?
C32 C33 H33 121.8 . . ?
F32 C32 C33 115.3(3) . . ?
F32 C32 C31 118.4(3) . . ?
C33 C32 C31 126.4(3) . . ?
C34 C35 C36 116.5(3) . . ?
C34 C35 H35 121.7 . . ?
C36 C35 H35 121.7 . . ?
C35 C34 F34 118.7(3) . . ?
C35 C34 C33 123.2(3) . . ?
F34 C34 C33 118.1(4) . . ?
C47 N1 N2 116.9(2) . . ?
N1 N2 B1 113.6(2) . . ?
N1 N2 H2A 108.8 . . ?
B1 N2 H2A 108.8 . . ?
N1 N2 H2B 108.8 . . ?
B1 N2 H2B 108.8 . . ?
H2A N2 H2B 107.7 . . ?
C42 C41 C46 119.6(3) . . ?
C42 C41 C47 120.9(3) . . ?
C46 C41 C47 119.3(3) . . ?
C45 C46 C41 120.2(3) . . ?
C45 C46 H46 119.9 . . ?
C41 C46 H46 119.9 . . ?
C44 C45 C46 120.2(4) . . ?
C44 C45 H45 119.9 . . ?
C46 C45 H45 119.9 . . ?
C43 C44 C45 119.8(4) . . ?
C43 C44 H44 120.1 . . ?
C45 C44 H44 120.1 . . ?
C41 C42 C43 119.7(3) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C44 C43 C42 120.5(4) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
N1 C47 C48 115.6(3) . . ?
N1 C47 C41 126.2(3) . . ?
C48 C47 C41 118.1(3) . . ?
C49 C48 C50 118.8(3) . . ?
C49 C48 C47 120.7(3) . . ?
C50 C48 C47 120.5(3) . . ?
C50 C49 C48 120.3(3) 2_566 . ?
C50 C49 H49 119.9 2_566 . ?
C48 C49 H49 119.9 . . ?
C49 C50 C48 120.9(3) 2_566 . ?
C49 C50 H50 119.5 2_566 . ?
C48 C50 H50 119.5 . . ?
Cl1 C1SA Cl2A 115.3(4) . . ?
Cl1 C1SA H1S1 108.5 . . ?
Cl2A C1SA H1S1 108.5 . . ?
Cl1 C1SA H1S2 108.5 . . ?
Cl2A C1SA H1S2 108.5 . . ?
H1S1 C1SA H1S2 107.5 . . ?
Cl2B C1SB Cl1 115.1(7) . . ?
Cl2B C1SB H1S3 108.5 . . ?
Cl1 C1SB H1S3 108.5 . . ?
Cl2B C1SB H1S4 108.5 . . ?
Cl1 C1SB H1S4 108.5 . . ?
H1S3 C1SB H1S4 107.5 . . ?

_refine_diff_density_max         0.655
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.057


_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_rm1835
_database_code_depnum_ccdc_archive 'CCDC 1897206'
loop_
_audit_author_name
_audit_author_address
'Theo Gazis'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-14 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_rm1835              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note  
RESPONSE: A small number of low angle reflections were obscured by
          the beamstop. Nevertheless this provided 99.8% of data to 
          25.4 degrees in theta and additional data were collected up 
          to 29.65 degrees affording a final data:parameter ratio of
          6315:388 which was more than adequate for refinement. 
;
# end Validation Reply Form
_audit_creation_date             2019-02-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H18 B F9 N2'
_chemical_formula_sum            'C31 H18 B F9 N2'
_chemical_formula_weight         600.28
_chemical_melting_point          ?
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'

_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                   9.5166(4)
_cell_length_b                   21.8157(8)
_cell_length_c                   13.1104(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.132(4)
_cell_angle_gamma                90
_cell_volume                     2687.37(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6947
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.8590
_cell_measurement_theta_min      4.0440
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over 
a multifaceted crystal model. Empirical absorption correction using 
spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.106
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.830
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14765
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.652
_diffrn_reflns_theta_min         3.283
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.830
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5183
_reflns_number_total             6315
_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 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    ?
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         6315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.062
_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)+(0.0351P)²+1.3302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1045
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H3(0.04) H4(0.049) H5(0.046) H6(0.044) H7(0.037) H9(0.047)
 H10(0.064) H11(0.06) H12(0.05) H13(0.038) H16(0.036) H18(0.037) H22(0.037)
 H24(0.04) H28(0.034) H30(0.037) H2A(0.026) H2B(0.026)
 Fixed X: H3(1.20828) H4(1.32417) H5(1.200037) H6(0.957549) H7(0.840042)
 H9(0.720843) H10(0.477852) H11(0.39148) H12(0.545907) H13(0.78832)
 H16(0.658628) H18(1.013832) H22(1.472472) H24(1.453369) H28(0.804261)
 H30(0.911025) H2A(0.85748) H2B(0.968878)
 Fixed Y: H3(0.978384) H4(1.066251) H5(1.157158) H6(1.159101) H7(1.071098)
 H9(0.945811) H10(0.941291) H11(0.945505) H12(0.956992) H13(0.964437)
 H16(0.807728) H18(0.902545) H22(0.77021) H24(0.826632) H28(0.669038)
 H30(0.593487) H2A(0.861951) H2B(0.849243)
 Fixed Z: H3(-0.154698) H4(-0.191691) H5(-0.2244) H6(-0.222894) H7(-0.18732)
 H9(-0.037332) H10(-0.095776) H11(-0.269854) H12(-0.387026) H13(-0.330362) H16(-
 0.441959) H18(-0.466942) H22(-0.222251) H24(0.067712) H28(0.075113) H30(-
 0.18231) H2A(-0.097371) H2B(-0.01222)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.93722(16) 0.95842(7) -0.14334(11) 0.0223(3) Uani 1 1 d . . . . .
C2 C 1.01154(16) 1.01517(7) -0.16688(11) 0.0242(3) Uani 1 1 d . . . . .
C3 C 1.15727(18) 1.01461(8) -0.16849(13) 0.0337(4) Uani 1 1 d . . . . .
H3 H 1.208280 0.978384 -0.154698 0.040 Uiso 1 1 calc R U . . .
C4 C 1.2268(2) 1.06727(8) -0.19035(15) 0.0405(4) Uani 1 1 d . . . . .
H4 H 1.324170 1.066251 -0.191691 0.049 Uiso 1 1 calc R U . . .
C5 C 1.1527(2) 1.12162(8) -0.21032(14) 0.0384(4) Uani 1 1 d . . . . .
H5 H 1.200037 1.157158 -0.224400 0.046 Uiso 1 1 calc R U . . .
C6 C 1.0080(2) 1.12272(8) -0.20919(14) 0.0370(4) Uani 1 1 d . . . . .
H6 H 0.957549 1.159101 -0.222894 0.044 Uiso 1 1 calc R U . . .
C7 C 0.93763(18) 1.06997(7) -0.18777(13) 0.0304(3) Uani 1 1 d . . . . .
H7 H 0.840042 1.071098 -0.187320 0.037 Uiso 1 1 calc R U . . .
C8 C 0.78011(16) 0.95458(7) -0.17826(12) 0.0255(3) Uani 1 1 d . . . . .
C9 C 0.68637(19) 0.94815(9) -0.10768(15) 0.0390(4) Uani 1 1 d . . . . .
H9 H 0.720843 0.945811 -0.037332 0.047 Uiso 1 1 calc R U . . .
C10 C 0.5407(2) 0.94524(10) -0.1429(2) 0.0530(6) Uani 1 1 d . . . . .
H10 H 0.477852 0.941291 -0.095776 0.064 Uiso 1 1 calc R U . . .
C11 C 0.4889(2) 0.94816(9) -0.24688(19) 0.0501(5) Uani 1 1 d . . . . .
H11 H 0.391480 0.945505 -0.269854 0.060 Uiso 1 1 calc R U . . .
C12 C 0.5811(2) 0.95498(8) -0.31675(16) 0.0420(5) Uani 1 1 d . . . . .
H12 H 0.545907 0.956992 -0.387026 0.050 Uiso 1 1 calc R U . . .
C13 C 0.72652(18) 0.95890(7) -0.28285(13) 0.0313(4) Uani 1 1 d . . . . .
H13 H 0.788320 0.964437 -0.330362 0.038 Uiso 1 1 calc R U . . .
C14 C 0.94607(15) 0.82239(7) -0.26582(11) 0.0208(3) Uani 1 1 d . . . . .
C15 C 0.81128(16) 0.80566(7) -0.31486(11) 0.0236(3) Uani 1 1 d . . . . .
C16 C 0.74942(17) 0.82108(8) -0.41407(12) 0.0299(3) Uani 1 1 d . . . . .
H16 H 0.658628 0.807728 -0.441959 0.036 Uiso 1 1 calc R U . . .
C17 C 0.82799(18) 0.85684(8) -0.46913(12) 0.0321(4) Uani 1 1 d . . . . .
C18 C 0.96144(18) 0.87795(8) -0.42885(12) 0.0306(4) Uani 1 1 d . . . . .
H18 H 1.013832 0.902545 -0.466942 0.037 Uiso 1 1 calc R U . . .
C19 C 1.01349(16) 0.86048(7) -0.32825(11) 0.0236(3) Uani 1 1 d . . . . .
C20 C 1.18460(15) 0.80149(6) -0.12008(11) 0.0214(3) Uani 1 1 d . . . . .
C21 C 1.27301(16) 0.78345(7) -0.18987(12) 0.0243(3) Uani 1 1 d . . . . .
C22 C 1.41980(17) 0.78206(8) -0.17159(13) 0.0312(4) Uani 1 1 d . . . . .
H22 H 1.472472 0.770210 -0.222251 0.037 Uiso 1 1 calc R U . . .
C23 C 1.48389(17) 0.79914(8) -0.07434(14) 0.0349(4) Uani 1 1 d . . . . .
C24 C 1.40852(17) 0.81576(8) 0.00195(13) 0.0335(4) Uani 1 1 d . . . . .
H24 H 1.453369 0.826632 0.067712 0.040 Uiso 1 1 calc R U . . .
C25 C 1.26228(17) 0.81547(7) -0.02424(11) 0.0259(3) Uani 1 1 d . . . . .
C26 C 0.94887(15) 0.73821(7) -0.10736(11) 0.0206(3) Uani 1 1 d . . . . .
C27 C 0.89367(15) 0.72739(7) -0.01707(11) 0.0222(3) Uani 1 1 d . . . . .
C28 C 0.84168(17) 0.67246(7) 0.01400(12) 0.0280(3) Uani 1 1 d . . . . .
H28 H 0.804261 0.669038 0.075113 0.034 Uiso 1 1 calc R U . . .
C29 C 0.84832(18) 0.62334(7) -0.05018(13) 0.0301(3) Uani 1 1 d . . . . .
C30 C 0.90511(18) 0.62735(7) -0.14011(13) 0.0304(3) Uani 1 1 d . . . . .
H30 H 0.911025 0.593487 -0.182310 0.037 Uiso 1 1 calc R U . . .
C31 C 0.95272(17) 0.68440(7) -0.16411(11) 0.0257(3) Uani 1 1 d . . . . .
B1 B 1.01082(17) 0.80307(7) -0.14636(12) 0.0198(3) Uani 1 1 d . . . . .
N1 N 1.01692(13) 0.91677(6) -0.09516(9) 0.0227(3) Uani 1 1 d . . . . .
N2 N 0.95132(13) 0.85868(6) -0.07907(9) 0.0219(3) Uani 1 1 d . . . . .
H2A H 0.857480 0.861951 -0.097371 0.026 Uiso 1 1 calc R U . . .
H2B H 0.968878 0.849243 -0.012220 0.026 Uiso 1 1 calc R U . . .
F1 F 0.72855(9) 0.77137(5) -0.26118(7) 0.0334(2) Uani 1 1 d . . . . .
F2 F 0.77166(13) 0.87344(6) -0.56649(8) 0.0523(3) Uani 1 1 d . . . . .
F3 F 1.14310(9) 0.88434(4) -0.28977(7) 0.0289(2) Uani 1 1 d . . . . .
F4 F 1.21307(10) 0.76618(4) -0.28649(7) 0.0296(2) Uani 1 1 d . . . . .
F5 F 1.62799(11) 0.80020(6) -0.05307(9) 0.0524(3) Uani 1 1 d . . . . .
F6 F 1.18888(10) 0.82985(5) 0.05381(7) 0.0336(2) Uani 1 1 d . . . . .
F7 F 0.89117(10) 0.77451(4) 0.05102(6) 0.0284(2) Uani 1 1 d . . . . .
F8 F 0.79867(12) 0.56818(5) -0.02331(8) 0.0436(3) Uani 1 1 d . . . . .
F9 F 1.00975(12) 0.68766(4) -0.25244(7) 0.0367(2) 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
C1 C2 1.482(2) . ?
C1 C8 1.495(2) . ?
C1 N1 1.2837(19) . ?
C2 C3 1.390(2) . ?
C2 C7 1.392(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(2) . ?
C8 C13 1.388(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(2) . ?
C14 C19 1.392(2) . ?
C14 B1 1.644(2) . ?
C15 C16 1.381(2) . ?
C15 F1 1.3603(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.364(2) . ?
C17 C18 1.375(2) . ?
C17 F2 1.3531(17) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(2) . ?
C19 F3 1.3599(17) . ?
C20 C21 1.394(2) . ?
C20 C25 1.387(2) . ?
C20 B1 1.635(2) . ?
C21 C22 1.380(2) . ?
C21 F4 1.3574(17) . ?
C22 H22 0.9300 . ?
C22 C23 1.375(2) . ?
C23 C24 1.369(3) . ?
C23 F5 1.3555(18) . ?
C24 H24 0.9300 . ?
C24 C25 1.380(2) . ?
C25 F6 1.3639(18) . ?
C26 C27 1.389(2) . ?
C26 C31 1.393(2) . ?
C26 B1 1.645(2) . ?
C27 C28 1.382(2) . ?
C27 F7 1.3641(17) . ?
C28 H28 0.9300 . ?
C28 C29 1.370(2) . ?
C29 C30 1.376(2) . ?
C29 F8 1.3595(18) . ?
C30 H30 0.9300 . ?
C30 C31 1.378(2) . ?
C31 F9 1.3565(17) . ?
B1 N2 1.652(2) . ?
N1 N2 1.4429(17) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C8 118.05(13) . . ?
N1 C1 C2 115.43(13) . . ?
N1 C1 C8 126.52(14) . . ?
C3 C2 C1 120.38(14) . . ?
C3 C2 C7 118.60(15) . . ?
C7 C2 C1 121.02(14) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.56(16) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.44(17) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.53(16) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.26(17) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.60(16) . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C1 121.20(15) . . ?
C13 C8 C1 119.44(14) . . ?
C13 C8 C9 119.35(15) . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.62(18) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.58(19) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.96(18) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.22(19) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.24(17) . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C19 111.25(13) . . ?
C15 C14 B1 123.53(13) . . ?
C19 C14 B1 125.09(13) . . ?
C16 C15 C14 126.57(15) . . ?
F1 C15 C14 118.21(13) . . ?
F1 C15 C16 115.21(13) . . ?
C15 C16 H16 121.6 . . ?
C17 C16 C15 116.76(15) . . ?
C17 C16 H16 121.6 . . ?
C16 C17 C18 122.60(14) . . ?
F2 C17 C16 118.95(15) . . ?
F2 C17 C18 118.43(16) . . ?
C17 C18 H18 121.9 . . ?
C17 C18 C19 116.23(15) . . ?
C19 C18 H18 121.9 . . ?
C18 C19 C14 126.49(14) . . ?
F3 C19 C14 119.06(12) . . ?
F3 C19 C18 114.44(13) . . ?
C21 C20 B1 124.27(12) . . ?
C25 C20 C21 111.48(13) . . ?
C25 C20 B1 124.20(13) . . ?
C22 C21 C20 126.30(14) . . ?
F4 C21 C20 118.86(13) . . ?
F4 C21 C22 114.83(14) . . ?
C21 C22 H22 121.8 . . ?
C23 C22 C21 116.30(15) . . ?
C23 C22 H22 121.8 . . ?
C24 C23 C22 122.86(15) . . ?
F5 C23 C22 118.75(16) . . ?
F5 C23 C24 118.39(15) . . ?
C23 C24 H24 121.9 . . ?
C23 C24 C25 116.22(15) . . ?
C25 C24 H24 121.9 . . ?
C24 C25 C20 126.73(15) . . ?
F6 C25 C20 117.87(13) . . ?
F6 C25 C24 115.39(13) . . ?
C27 C26 C31 110.93(13) . . ?
C27 C26 B1 127.84(13) . . ?
C31 C26 B1 121.17(12) . . ?
C28 C27 C26 126.85(14) . . ?
F7 C27 C26 118.54(13) . . ?
F7 C27 C28 114.59(13) . . ?
C27 C28 H28 121.8 . . ?
C29 C28 C27 116.33(14) . . ?
C29 C28 H28 121.8 . . ?
C28 C29 C30 122.64(15) . . ?
F8 C29 C28 118.77(15) . . ?
F8 C29 C30 118.58(15) . . ?
C29 C30 H30 121.9 . . ?
C29 C30 C31 116.19(15) . . ?
C31 C30 H30 121.9 . . ?
C30 C31 C26 126.99(14) . . ?
F9 C31 C26 117.36(13) . . ?
F9 C31 C30 115.66(14) . . ?
C14 B1 C26 114.70(12) . . ?
C14 B1 N2 102.24(11) . . ?
C20 B1 C14 114.81(12) . . ?
C20 B1 C26 108.47(11) . . ?
C20 B1 N2 108.90(11) . . ?
C26 B1 N2 107.19(11) . . ?
C1 N1 N2 117.26(12) . . ?
B1 N2 H2A 109.2 . . ?
B1 N2 H2B 109.2 . . ?
N1 N2 B1 111.97(11) . . ?
N1 N2 H2A 109.2 . . ?
N1 N2 H2B 109.2 . . ?
H2A N2 H2B 107.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_RM1837c
_database_code_depnum_ccdc_archive 'CCDC 1897208'
loop_
_audit_author_name
_audit_author_address
'Theo Gazis'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-14 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H16 B2 F18 N2'
_chemical_formula_sum            'C36 H16 B2 F18 N2'
_chemical_formula_weight         840.13

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   15.7866(8)
_cell_length_b                   9.6410(4)
_cell_length_c                   22.4406(11)
_cell_angle_alpha                90
_cell_angle_beta                 108.694(6)
_cell_angle_gamma                90
_cell_volume                     3235.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    4127
_cell_measurement_theta_min      4.910
_cell_measurement_theta_max      29.375

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_F_000             1672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.174
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration 
over a multifaceted crystal model. Empirical absorption 
correction using spherical harmonics implemented in SCALE3 
ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_measurement_device_type  'SuperNova (Mo)'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8430
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.337
_diffrn_reflns_theta_max         29.568
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3884
_reflns_number_gt                3261
_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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    Mercury
_computing_publication_material  ?
_refine_special_details          
;
Structure solved by direct methods to reveal all non-H atoms. Half a molecule 
in the asymmetric unit. All atoms refined anisotropically. H atoms added at 
calculated positions except the two N-H H atoms which were located in the 
difference map and freely refined with Uiso riding on the attached N atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+3.6479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3884
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
B1 B 0.19580(11) 0.12530(16) 0.17000(7) 0.0187(3) Uani 1 1 d . . . . .
C11 C 0.27025(10) 0.17879(15) 0.13902(7) 0.0208(3) Uani 1 1 d . . . . .
C15 C 0.41734(11) 0.14744(19) 0.12349(8) 0.0305(4) Uani 1 1 d . . . . .
H15 H 0.468821 0.094488 0.130296 0.037 Uiso 1 1 calc R U . . .
C13 C 0.32670(11) 0.34458(18) 0.07651(7) 0.0301(4) Uani 1 1 d . . . . .
H13 H 0.318180 0.425347 0.052655 0.036 Uiso 1 1 calc R U . . .
C16 C 0.35121(10) 0.11107(16) 0.14839(7) 0.0241(3) Uani 1 1 d . . . . .
C12 C 0.26319(11) 0.29720(16) 0.10217(7) 0.0245(3) Uani 1 1 d . . . . .
C14 C 0.40275(11) 0.2665(2) 0.08804(8) 0.0322(4) Uani 1 1 d . . . . .
C21 C 0.09496(10) 0.18627(14) 0.13773(7) 0.0196(3) Uani 1 1 d . . . . .
C24 C -0.08089(10) 0.27171(16) 0.07335(7) 0.0252(3) Uani 1 1 d . . . . .
C23 C -0.03465(11) 0.20050(17) 0.04080(7) 0.0271(3) Uani 1 1 d . . . . .
H23 H -0.060086 0.179725 -0.001688 0.032 Uiso 1 1 calc R U . . .
C22 C 0.05118(10) 0.16139(16) 0.07412(7) 0.0235(3) Uani 1 1 d . . . . .
C26 C 0.04060(10) 0.25416(15) 0.16565(7) 0.0214(3) Uani 1 1 d . . . . .
C25 C -0.04561(10) 0.30069(16) 0.13627(7) 0.0250(3) Uani 1 1 d . . . . .
H25 H -0.077708 0.348733 0.157919 0.030 Uiso 1 1 calc R U . . .
C31 C 0.18531(10) -0.04302(14) 0.17412(7) 0.0200(3) Uani 1 1 d . . . . .
C33 C 0.18432(11) -0.28033(16) 0.13209(7) 0.0257(3) Uani 1 1 d . . . . .
H33 H 0.196400 -0.339647 0.103142 0.031 Uiso 1 1 calc R U . . .
C35 C 0.13001(10) -0.24410(16) 0.21991(7) 0.0249(3) Uani 1 1 d . . . . .
H35 H 0.105815 -0.278121 0.249719 0.030 Uiso 1 1 calc R U . . .
C32 C 0.20082(10) -0.13938(15) 0.13216(7) 0.0224(3) Uani 1 1 d . . . . .
C36 C 0.14894(10) -0.10544(15) 0.21608(7) 0.0219(3) Uani 1 1 d . . . . .
C34 C 0.14928(11) -0.32841(15) 0.17680(7) 0.0253(3) Uani 1 1 d . . . . .
F12 F 0.18884(7) 0.37686(10) 0.09012(5) 0.0355(2) Uani 1 1 d . . . . .
F14 F 0.46625(7) 0.30982(14) 0.06402(5) 0.0483(3) Uani 1 1 d . . . . .
F16 F 0.36882(6) -0.00175(10) 0.18662(4) 0.0310(2) Uani 1 1 d . . . . .
F22 F 0.09745(7) 0.09324(11) 0.04179(4) 0.0333(2) Uani 1 1 d . . . . .
F24 F -0.16467(6) 0.31587(11) 0.04196(5) 0.0350(2) Uani 1 1 d . . . . .
F26 F 0.07417(6) 0.28183(10) 0.22869(4) 0.0286(2) Uani 1 1 d . . . . .
F32 F 0.23314(6) -0.09491(9) 0.08685(4) 0.0282(2) Uani 1 1 d . . . . .
F34 F 0.13216(7) -0.46620(9) 0.17831(5) 0.0343(2) Uani 1 1 d . . . . .
F36 F 0.12749(6) -0.02094(9) 0.25854(4) 0.0289(2) Uani 1 1 d . . . . .
N1 N 0.23752(9) 0.17692(12) 0.24492(6) 0.0184(2) Uani 1 1 d . . . . .
H1A H 0.1986(12) 0.1613(18) 0.2668(8) 0.022 Uiso 1 1 d . U . . .
H1B H 0.2887(12) 0.1309(18) 0.2635(8) 0.022 Uiso 1 1 d . 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 C11 1.629(2) . ?
B1 C21 1.633(2) . ?
B1 C31 1.637(2) . ?
B1 N1 1.6728(19) . ?
C11 C16 1.390(2) . ?
C11 C12 1.393(2) . ?
C15 C14 1.373(3) . ?
C15 C16 1.378(2) . ?
C15 H15 0.9300 . ?
C13 C14 1.370(3) . ?
C13 C12 1.384(2) . ?
C13 H13 0.9300 . ?
C16 F16 1.3578(18) . ?
C12 F12 1.3554(19) . ?
C14 F14 1.3476(18) . ?
C21 C26 1.379(2) . ?
C21 C22 1.393(2) . ?
C24 F24 1.3526(17) . ?
C24 C25 1.370(2) . ?
C24 C23 1.371(2) . ?
C23 C22 1.374(2) . ?
C23 H23 0.9300 . ?
C22 F22 1.3533(17) . ?
C26 F26 1.3686(16) . ?
C26 C25 1.383(2) . ?
C25 H25 0.9300 . ?
C31 C36 1.387(2) . ?
C31 C32 1.399(2) . ?
C33 C34 1.372(2) . ?
C33 C32 1.384(2) . ?
C33 H33 0.9300 . ?
C35 C34 1.370(2) . ?
C35 C36 1.379(2) . ?
C35 H35 0.9300 . ?
C32 F32 1.3455(17) . ?
C36 F36 1.3760(17) . ?
C34 F34 1.3582(17) . ?
N1 N1 1.461(2) 7 ?
N1 H1A 0.915(18) . ?
N1 H1B 0.899(18) . ?

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
C11 B1 C21 115.53(12) . . ?
C11 B1 C31 115.97(12) . . ?
C21 B1 C31 106.27(11) . . ?
C11 B1 N1 103.25(11) . . ?
C21 B1 N1 110.64(11) . . ?
C31 B1 N1 104.63(11) . . ?
C16 C11 C12 111.68(13) . . ?
C16 C11 B1 122.75(13) . . ?
C12 C11 B1 125.55(13) . . ?
C14 C15 C16 116.07(16) . . ?
C14 C15 H15 122.0 . . ?
C16 C15 H15 122.0 . . ?
C14 C13 C12 116.62(16) . . ?
C14 C13 H13 121.7 . . ?
C12 C13 H13 121.7 . . ?
F16 C16 C15 115.58(14) . . ?
F16 C16 C11 117.65(13) . . ?
C15 C16 C11 126.77(15) . . ?
F12 C12 C13 115.25(14) . . ?
F12 C12 C11 118.82(13) . . ?
C13 C12 C11 125.92(15) . . ?
F14 C14 C13 118.25(17) . . ?
F14 C14 C15 118.87(16) . . ?
C13 C14 C15 122.88(15) . . ?
C26 C21 C22 111.75(13) . . ?
C26 C21 B1 129.03(13) . . ?
C22 C21 B1 119.05(12) . . ?
F24 C24 C25 118.62(14) . . ?
F24 C24 C23 118.61(14) . . ?
C25 C24 C23 122.77(14) . . ?
C24 C23 C22 116.61(14) . . ?
C24 C23 H23 121.7 . . ?
C22 C23 H23 121.7 . . ?
F22 C22 C23 116.67(13) . . ?
F22 C22 C21 117.21(13) . . ?
C23 C22 C21 126.11(14) . . ?
F26 C26 C21 118.09(13) . . ?
F26 C26 C25 115.17(13) . . ?
C21 C26 C25 126.73(14) . . ?
C24 C25 C26 115.96(14) . . ?
C24 C25 H25 122.0 . . ?
C26 C25 H25 122.0 . . ?
C36 C31 C32 111.62(13) . . ?
C36 C31 B1 122.67(13) . . ?
C32 C31 B1 125.28(13) . . ?
C34 C33 C32 116.80(14) . . ?
C34 C33 H33 121.6 . . ?
C32 C33 H33 121.6 . . ?
C34 C35 C36 115.45(14) . . ?
C34 C35 H35 122.3 . . ?
C36 C35 H35 122.3 . . ?
F32 C32 C33 115.41(13) . . ?
F32 C32 C31 119.18(13) . . ?
C33 C32 C31 125.41(14) . . ?
F36 C36 C35 115.13(13) . . ?
F36 C36 C31 117.41(13) . . ?
C35 C36 C31 127.45(14) . . ?
F34 C34 C35 118.13(14) . . ?
F34 C34 C33 118.60(14) . . ?
C35 C34 C33 123.26(14) . . ?
N1 N1 B1 116.32(13) 7 . ?
N1 N1 H1A 105.6(11) 7 . ?
B1 N1 H1A 112.1(11) . . ?
N1 N1 H1B 104.2(11) 7 . ?
B1 N1 H1B 109.0(11) . . ?
H1A N1 H1B 109.1(15) . . ?

_refine_diff_density_max         0.347
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_RM1834b-2
_database_code_depnum_ccdc_archive 'CCDC 1897209'
loop_
_audit_author_name
_audit_author_address
'Theo Gazis'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-14 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H13 B F6 N2'
_chemical_formula_sum            'C25 H13 B F6 N2'
_chemical_formula_weight         466.18

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.8884(9)
_cell_length_b                   10.6742(5)
_cell_length_c                   14.1291(7)
_cell_angle_alpha                90
_cell_angle_beta                 115.392(7)
_cell_angle_gamma                90
_cell_volume                     2028.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    170.03(10)
_cell_measurement_reflns_used    4971
_cell_measurement_theta_min      3.6940
_cell_measurement_theta_max      29.1730

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_min          0.115
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.601
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170.03(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  
'Agilent Supernova Dual Atlas with CCD Detector'
_diffrn_measurement_method       'Omega scans'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_reflns_number            10152
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.328
_diffrn_reflns_theta_max         27.871
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4614
_reflns_number_gt                3746
_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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_structure_solution    SHELLXS
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL and Mercury'
_computing_publication_material  XCIF

_refine_special_details          
;
Structure was solved by direct methods to reveal all non atoms. Subsequent 
non H atoms were revealed by difference map and refined anisotropically. H
atoms were added at calculated positions using a riding model.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+0.7555P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Direct
_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         4614
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.25655(12) 0.63436(16) 1.07817(12) 0.0254(3) Uani 1 1 d . . . . .
C13 C 0.03481(10) 0.81768(14) 0.95212(10) 0.0245(3) Uani 1 1 d . . . . .
C7 C -0.10285(11) 0.94717(14) 0.86166(11) 0.0258(3) Uani 1 1 d . . . . .
C12 C -0.00602(11) 0.92040(14) 0.87538(10) 0.0251(3) Uani 1 1 d . . . . .
C5 C -0.04579(11) 0.78150(14) 0.98352(11) 0.0256(3) Uani 1 1 d . . . . .
C6 C -0.12804(10) 0.86011(14) 0.92764(11) 0.0255(3) Uani 1 1 d . . . . .
C2 C -0.22279(12) 0.75546(16) 1.00403(12) 0.0328(3) Uani 1 1 d . . . . .
H2 H -0.2816 0.7460 1.0114 0.039 Uiso 1 1 calc R U . . .
C8 C -0.15666(12) 1.04328(15) 0.79571(12) 0.0305(3) Uani 1 1 d . . . . .
H8 H -0.2208 1.0618 0.7869 0.037 Uiso 1 1 calc R U . . .
C9 C -0.11240(12) 1.11119(16) 0.74319(12) 0.0326(3) Uani 1 1 d . . . . .
H9 H -0.1474 1.1760 0.6987 0.039 Uiso 1 1 calc R U . . .
C3 C -0.14277(12) 0.67822(16) 1.05941(13) 0.0339(4) Uani 1 1 d . . . . .
H3 H -0.1482 0.6175 1.1039 0.041 Uiso 1 1 calc R U . . .
C11 C 0.03815(11) 0.98817(15) 0.82278(11) 0.0290(3) Uani 1 1 d . . . . .
H11 H 0.1025 0.9702 0.8318 0.035 Uiso 1 1 calc R U . . .
C1 C -0.21617(11) 0.84699(15) 0.93761(12) 0.0298(3) Uani 1 1 d . . . . .
H1 H -0.2701 0.8988 0.9003 0.036 Uiso 1 1 calc R U . . .
C4 C -0.05397(12) 0.69033(15) 1.04932(12) 0.0317(3) Uani 1 1 d . . . . .
H4 H -0.0006 0.6376 1.0865 0.038 Uiso 1 1 calc R U . . .
C10 C -0.01661(12) 1.08373(16) 0.75618(12) 0.0330(4) Uani 1 1 d . . . . .
H10 H 0.0113 1.1300 0.7198 0.040 Uiso 1 1 calc R U . . .
N1 N 0.12404(9) 0.77933(12) 0.97661(9) 0.0262(3) Uani 1 1 d . . . . .
N2 N 0.16299(9) 0.68717(12) 1.05165(9) 0.0285(3) Uani 1 1 d . . . . .
H2A H 0.1284 0.6612 1.0833 0.034 Uiso 1 1 calc R U . . .
C20 C 0.29438(11) 0.52500(15) 1.16107(11) 0.0276(3) Uani 1 1 d . . . . .
C14 C 0.31904(10) 0.68459(14) 1.01953(11) 0.0253(3) Uani 1 1 d . . . . .
C21 C 0.23397(11) 0.45845(16) 1.19651(12) 0.0302(3) Uani 1 1 d . . . . .
C22 C 0.26151(13) 0.35673(16) 1.26236(12) 0.0351(4) Uani 1 1 d . . . . .
H22 H 0.2174 0.3172 1.2834 0.042 Uiso 1 1 calc R U . . .
C25 C 0.39085(11) 0.47789(16) 1.20251(12) 0.0318(3) Uani 1 1 d . . . . .
C23 C 0.35790(14) 0.31676(17) 1.29545(13) 0.0387(4) Uani 1 1 d . . . . .
C19 C 0.35393(11) 0.60779(15) 0.96361(11) 0.0286(3) Uani 1 1 d . . . . .
C15 C 0.34347(12) 0.80933(15) 1.01783(13) 0.0340(4) Uani 1 1 d . . . . .
C24 C 0.42444(13) 0.37532(18) 1.26697(13) 0.0389(4) Uani 1 1 d . . . . .
H24 H 0.4895 0.3469 1.2902 0.047 Uiso 1 1 calc R U . . .
C18 C 0.40739(13) 0.64649(19) 0.91017(13) 0.0393(4) Uani 1 1 d . . . . .
H18 H 0.4290 0.5904 0.8740 0.047 Uiso 1 1 calc R U . . .
C16 C 0.39585(14) 0.85692(18) 0.96551(17) 0.0491(5) Uani 1 1 d . . . . .
H16 H 0.4093 0.9420 0.9657 0.059 Uiso 1 1 calc R U . . .
C17 C 0.42703(14) 0.7718(2) 0.91319(16) 0.0487(5) Uani 1 1 d . . . . .
F1 F 0.13790(7) 0.49472(10) 1.16300(8) 0.0407(3) Uani 1 1 d . . . . .
F4 F 0.33390(8) 0.48428(9) 0.96132(8) 0.0408(3) Uani 1 1 d . . . . .
F3 F 0.45924(7) 0.53667(10) 1.17892(8) 0.0405(3) Uani 1 1 d . . . . .
F6 F 0.31853(8) 0.89066(10) 1.07593(10) 0.0502(3) Uani 1 1 d . . . . .
F2 F 0.38753(9) 0.21506(11) 1.35770(9) 0.0583(3) Uani 1 1 d . . . . .
F5 F 0.48156(11) 0.81413(15) 0.86403(13) 0.0812(5) 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
B1 N2 1.397(2) . ?
B1 C20 1.577(2) . ?
B1 C14 1.581(2) . ?
C13 N1 1.2877(19) . ?
C13 C12 1.477(2) . ?
C13 C5 1.497(2) . ?
C7 C8 1.387(2) . ?
C7 C12 1.399(2) . ?
C7 C6 1.474(2) . ?
C12 C11 1.388(2) . ?
C5 C4 1.387(2) . ?
C5 C6 1.413(2) . ?
C6 C1 1.386(2) . ?
C2 C3 1.383(2) . ?
C2 C1 1.387(2) . ?
C2 H2 0.9300 . ?
C8 C9 1.389(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(2) . ?
C9 H9 0.9300 . ?
C3 C4 1.395(2) . ?
C3 H3 0.9300 . ?
C11 C10 1.390(2) . ?
C11 H11 0.9300 . ?
C1 H1 0.9300 . ?
C4 H4 0.9300 . ?
C10 H10 0.9300 . ?
N1 N2 1.3787(17) . ?
N2 H2A 0.8600 . ?
C20 C25 1.392(2) . ?
C20 C21 1.397(2) . ?
C14 C15 1.383(2) . ?
C14 C19 1.385(2) . ?
C21 F1 1.3561(17) . ?
C21 C22 1.373(2) . ?
C22 C23 1.373(2) . ?
C22 H22 0.9300 . ?
C25 F3 1.3538(18) . ?
C25 C24 1.374(2) . ?
C23 F2 1.3468(19) . ?
C23 C24 1.370(3) . ?
C19 F4 1.3490(18) . ?
C19 C18 1.375(2) . ?
C15 F6 1.3517(19) . ?
C15 C16 1.381(2) . ?
C24 H24 0.9300 . ?
C18 C17 1.366(3) . ?
C18 H18 0.9300 . ?
C16 C17 1.372(3) . ?
C16 H16 0.9300 . ?
C17 F5 1.353(2) . ?

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
N2 B1 C20 119.71(13) . . ?
N2 B1 C14 117.76(13) . . ?
C20 B1 C14 122.49(13) . . ?
N1 C13 C12 119.06(13) . . ?
N1 C13 C5 134.74(14) . . ?
C12 C13 C5 106.20(12) . . ?
C8 C7 C12 120.56(14) . . ?
C8 C7 C6 131.38(14) . . ?
C12 C7 C6 108.06(13) . . ?
C11 C12 C7 121.05(14) . . ?
C11 C12 C13 129.74(13) . . ?
C7 C12 C13 109.18(12) . . ?
C4 C5 C6 119.14(13) . . ?
C4 C5 C13 133.75(14) . . ?
C6 C5 C13 107.08(13) . . ?
C1 C6 C5 120.97(14) . . ?
C1 C6 C7 129.56(14) . . ?
C5 C6 C7 109.45(12) . . ?
C3 C2 C1 120.59(14) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C7 C8 C9 118.38(14) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C10 C9 C8 120.98(15) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C2 C3 C4 120.74(15) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C12 C11 C10 118.02(14) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C6 C1 C2 119.02(14) . . ?
C6 C1 H1 120.5 . . ?
C2 C1 H1 120.5 . . ?
C5 C4 C3 119.54(15) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C9 C10 C11 121.01(15) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C13 N1 N2 118.60(12) . . ?
N1 N2 B1 122.44(12) . . ?
N1 N2 H2A 118.8 . . ?
B1 N2 H2A 118.8 . . ?
C25 C20 C21 111.86(14) . . ?
C25 C20 B1 123.75(14) . . ?
C21 C20 B1 124.27(14) . . ?
C15 C14 C19 113.21(14) . . ?
C15 C14 B1 123.62(13) . . ?
C19 C14 B1 123.16(14) . . ?
F1 C21 C22 115.22(14) . . ?
F1 C21 C20 118.33(14) . . ?
C22 C21 C20 126.44(15) . . ?
C23 C22 C21 116.18(15) . . ?
C23 C22 H22 121.9 . . ?
C21 C22 H22 121.9 . . ?
F3 C25 C24 115.73(14) . . ?
F3 C25 C20 118.58(14) . . ?
C24 C25 C20 125.69(15) . . ?
F2 C23 C24 118.95(16) . . ?
F2 C23 C22 118.34(16) . . ?
C24 C23 C22 122.71(16) . . ?
F4 C19 C18 117.04(14) . . ?
F4 C19 C14 117.33(13) . . ?
C18 C19 C14 125.63(16) . . ?
F6 C15 C16 117.01(16) . . ?
F6 C15 C14 117.70(14) . . ?
C16 C15 C14 125.20(16) . . ?
C23 C24 C25 117.06(15) . . ?
C23 C24 H24 121.5 . . ?
C25 C24 H24 121.5 . . ?
C17 C18 C19 116.34(16) . . ?
C17 C18 H18 121.8 . . ?
C19 C18 H18 121.8 . . ?
C17 C16 C15 116.37(17) . . ?
C17 C16 H16 121.8 . . ?
C15 C16 H16 121.8 . . ?
F5 C17 C18 118.60(18) . . ?
F5 C17 C16 118.15(19) . . ?
C18 C17 C16 123.23(16) . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_RM1904
_database_code_depnum_ccdc_archive 'CCDC 1897211'
loop_
_audit_author_name
_audit_author_address
'Theo Gazis'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-14 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_RM1904              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         14 Note  
RESPONSE: small number of low angle reflections missing due to automated data
collection strategy - these low angle reflections likely masked by beamstop. 
Note 99.7% of reflections were measured to 50.48 deg in 2 theta. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H7 B F10 N2 O'
_chemical_formula_sum            'C19 H7 B F10 N2 O'
_chemical_formula_weight         480.08

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.8326(5)
_cell_length_b                   12.0001(7)
_cell_length_c                   13.9711(6)
_cell_angle_alpha                73.338(4)
_cell_angle_beta                 89.047(3)
_cell_angle_gamma                75.159(4)
_cell_volume                     1833.64(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5684
_cell_measurement_theta_min      3.514
_cell_measurement_theta_max      29.215

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.453
_exptl_crystal_size_mid          0.332
_exptl_crystal_size_min          0.217
_exptl_absorpt_coefficient_mu    0.178
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.421
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Supernova Mo Xray source'
_diffrn_measurement_device_type  'Supernova Dual, Atlas'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15395
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.396
_diffrn_reflns_theta_max         29.892
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8650
_reflns_number_gt                6398
_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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Structure solved by intrinsic phasing. All non0H atoms
refined anisotropically. H atoms added at calculated positions
except NH2 protons which were located in the difmap and refined with
Uiso riding on the N atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0773P)²+0.0964P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8650
_refine_ls_number_parameters     607
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1473
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
F20 F 0.60576(10) 0.53017(10) 0.47156(8) 0.0357(3) Uani 1 1 d . . . . .
F16 F 0.68775(11) 0.90319(11) 0.31945(9) 0.0426(3) Uani 1 1 d . . . . .
F19 F 0.52995(11) 0.60646(12) 0.63146(9) 0.0420(3) Uani 1 1 d . . . . .
O2 O 0.70264(11) 0.75019(13) 0.20214(9) 0.0296(3) Uani 1 1 d . . . . .
N4 N 0.59658(14) 0.60633(16) 0.26000(11) 0.0255(3) Uani 1 1 d . . . . .
H4A H 0.5304(19) 0.616(2) 0.2897(16) 0.031 Uiso 1 1 d . U . . .
H4B H 0.6137(18) 0.524(2) 0.2668(16) 0.031 Uiso 1 1 d . U . . .
F17 F 0.62579(11) 0.97176(11) 0.48233(10) 0.0463(3) Uani 1 1 d . . . . .
F11 F 0.90744(10) 0.71364(12) 0.33082(10) 0.0452(3) Uani 1 1 d . . . . .
F15 F 0.75293(10) 0.38420(11) 0.34139(10) 0.0421(3) Uani 1 1 d . . . . .
F12 F 1.11924(10) 0.55970(15) 0.39245(11) 0.0525(4) Uani 1 1 d . . . . .
F18 F 0.54521(11) 0.82565(13) 0.63916(9) 0.0470(3) Uani 1 1 d . . . . .
C38 C 0.64772(15) 0.71421(17) 0.38806(13) 0.0248(4) Uani 1 1 d . . . . .
F13 F 1.14852(10) 0.31987(15) 0.42819(11) 0.0578(4) Uani 1 1 d . . . . .
F14 F 0.96324(12) 0.23434(13) 0.40218(12) 0.0569(4) Uani 1 1 d . . . . .
N3 N 0.56861(13) 0.66995(15) 0.15316(11) 0.0277(3) Uani 1 1 d . . . . .
C26 C 0.63152(15) 0.74587(17) 0.13181(13) 0.0261(4) Uani 1 1 d . . . . .
C32 C 0.81984(15) 0.55707(18) 0.33199(13) 0.0258(4) Uani 1 1 d . . . . .
C37 C 0.60814(16) 0.64244(17) 0.47140(14) 0.0269(4) Uani 1 1 d . . . . .
C33 C 0.64999(16) 0.82622(18) 0.39463(14) 0.0291(4) Uani 1 1 d . . . . .
C36 C 0.57126(16) 0.67879(19) 0.55396(14) 0.0301(4) Uani 1 1 d . . . . .
C27 C 0.91858(16) 0.59554(19) 0.34664(14) 0.0305(4) Uani 1 1 d . . . . .
C35 C 0.57690(17) 0.79046(19) 0.55785(15) 0.0322(4) Uani 1 1 d . . . . .
C31 C 0.84117(16) 0.43335(19) 0.35331(14) 0.0303(4) Uani 1 1 d . . . . .
C25 C 0.62788(16) 0.82959(19) 0.03115(14) 0.0305(4) Uani 1 1 d . . . . .
C34 C 0.61704(16) 0.86445(18) 0.47786(15) 0.0317(4) Uani 1 1 d . . . . .
B2 B 0.69471(18) 0.6583(2) 0.29729(15) 0.0255(4) Uani 1 1 d . . . . .
C28 C 1.02753(16) 0.5181(2) 0.37887(15) 0.0363(5) Uani 1 1 d . . . . .
C30 C 0.94861(18) 0.35301(19) 0.38577(16) 0.0357(5) Uani 1 1 d . . . . .
C29 C 1.04277(17) 0.3961(2) 0.39812(15) 0.0382(5) Uani 1 1 d . . . . .
C20 C 0.7051(2) 0.9017(2) 0.00922(16) 0.0429(5) Uani 1 1 d . . . . .
H20 H 0.760585 0.897258 0.059416 0.051 Uiso 1 1 calc R U . . .
C24 C 0.5469(2) 0.8381(3) -0.04337(17) 0.0501(6) Uani 1 1 d . . . . .
H24 H 0.493345 0.789412 -0.029286 0.060 Uiso 1 1 calc R U . . .
C23 C 0.5441(2) 0.9171(3) -0.13769(18) 0.0608(8) Uani 1 1 d . . . . .
H23 H 0.488550 0.922279 -0.188193 0.073 Uiso 1 1 calc R U . . .
C22 C 0.6205(2) 0.9878(2) -0.15896(17) 0.0515(6) Uani 1 1 d . . . . .
H22 H 0.618063 1.042066 -0.223983 0.062 Uiso 1 1 calc R U . . .
C21 C 0.7013(2) 0.9800(3) -0.08576(17) 0.0540(7) Uani 1 1 d . . . . .
H21 H 0.754691 1.028864 -0.100681 0.065 Uiso 1 1 calc R U . . .
F1 F 0.62644(10) 0.47556(11) -0.00431(8) 0.0360(3) Uani 1 1 d . . . . .
F2 F 0.58311(10) 0.38725(12) 0.18883(9) 0.0403(3) Uani 1 1 d . . . . .
F5 F 0.88746(10) 0.10008(11) 0.00910(9) 0.0405(3) Uani 1 1 d . . . . .
F4 F 0.84498(11) 0.01427(12) 0.19965(9) 0.0463(3) Uani 1 1 d . . . . .
O1 O 0.82808(10) 0.26520(13) -0.17753(9) 0.0294(3) Uani 1 1 d . . . . .
F3 F 0.69487(12) 0.15673(13) 0.29263(9) 0.0473(3) Uani 1 1 d . . . . .
F6 F 1.01698(10) 0.29703(13) -0.06950(10) 0.0474(3) Uani 1 1 d . . . . .
N2 N 0.64761(13) 0.40655(16) -0.18296(12) 0.0249(3) Uani 1 1 d . . . . .
H2A H 0.5927(19) 0.387(2) -0.1458(16) 0.030 Uiso 1 1 d . U . . .
H2B H 0.6262(18) 0.485(2) -0.2090(16) 0.030 Uiso 1 1 d . U . . .
N1 N 0.65279(13) 0.35065(15) -0.26388(11) 0.0266(3) Uani 1 1 d . . . . .
F10 F 0.68935(10) 0.62789(12) -0.20224(11) 0.0478(3) Uani 1 1 d . . . . .
F7 F 1.15205(10) 0.45013(16) -0.08657(11) 0.0570(4) Uani 1 1 d . . . . .
C13 C 0.75711(15) 0.29123(18) -0.00646(14) 0.0265(4) Uani 1 1 d . . . . .
C8 C 0.68151(16) 0.35924(18) 0.04508(14) 0.0277(4) Uani 1 1 d . . . . .
C7 C 0.75481(15) 0.27527(17) -0.25165(13) 0.0234(4) Uani 1 1 d . . . . .
C12 C 0.81084(15) 0.17470(18) 0.04953(14) 0.0288(4) Uani 1 1 d . . . . .
F8 F 1.05701(13) 0.69055(16) -0.16073(12) 0.0639(4) Uani 1 1 d . . . . .
F9 F 0.82461(14) 0.77718(14) -0.21741(14) 0.0676(5) Uani 1 1 d . . . . .
C10 C 0.71420(17) 0.1998(2) 0.19613(14) 0.0326(4) Uani 1 1 d . . . . .
C9 C 0.65869(16) 0.31669(19) 0.14346(14) 0.0305(4) Uani 1 1 d . . . . .
C6 C 0.79112(15) 0.19710(18) -0.31646(13) 0.0263(4) Uani 1 1 d . . . . .
C1 C 0.72311(18) 0.2171(2) -0.40345(15) 0.0346(5) Uani 1 1 d . . . . .
H1 H 0.655478 0.283321 -0.422364 0.041 Uiso 1 1 calc R U . . .
C18 C 0.80473(17) 0.5780(2) -0.17164(15) 0.0340(5) Uani 1 1 d . . . . .
B1 B 0.77493(17) 0.3534(2) -0.12276(15) 0.0257(4) Uani 1 1 d . . . . .
C11 C 0.79054(17) 0.12794(19) 0.14911(15) 0.0318(4) Uani 1 1 d . . . . .
C19 C 0.84802(15) 0.45409(19) -0.13601(14) 0.0280(4) Uani 1 1 d . . . . .
C14 C 0.96667(16) 0.4155(2) -0.10767(14) 0.0321(4) Uani 1 1 d . . . . .
C2 C 0.7549(2) 0.1398(2) -0.46195(17) 0.0429(5) Uani 1 1 d . . . . .
H2 H 0.709080 0.153256 -0.521372 0.051 Uiso 1 1 calc R U . . .
C15 C 1.03699(17) 0.4931(2) -0.11534(15) 0.0390(5) Uani 1 1 d . . . . .
C5 C 0.89050(18) 0.1020(2) -0.29022(16) 0.0385(5) Uani 1 1 d . . . . .
H5 H 0.937927 0.089450 -0.231910 0.046 Uiso 1 1 calc R U . . .
C17 C 0.8717(2) 0.6589(2) -0.18009(17) 0.0422(5) Uani 1 1 d . . . . .
C16 C 0.98900(19) 0.6148(2) -0.15154(17) 0.0430(6) Uani 1 1 d . . . . .
C3 C 0.8527(2) 0.0435(2) -0.43431(18) 0.0464(6) Uani 1 1 d . . . . .
H3 H 0.873245 -0.010260 -0.473929 0.056 Uiso 1 1 calc R U . . .
C4 C 0.9208(2) 0.0252(2) -0.34922(19) 0.0482(6) Uani 1 1 d . . . . .
H4 H 0.988794 -0.040656 -0.330980 0.058 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
F20 C37 1.354(2) . ?
F16 C33 1.340(2) . ?
F19 C36 1.351(2) . ?
O2 C26 1.325(2) . ?
O2 B2 1.483(2) . ?
N4 N3 1.468(2) . ?
N4 B2 1.608(3) . ?
F17 C34 1.337(2) . ?
F11 C27 1.342(2) . ?
F15 C31 1.358(2) . ?
F12 C28 1.342(2) . ?
F18 C35 1.338(2) . ?
C38 C33 1.380(3) . ?
C38 C37 1.389(3) . ?
C38 B2 1.625(3) . ?
F13 C29 1.338(2) . ?
F14 C30 1.341(3) . ?
N3 C26 1.287(2) . ?
C26 C25 1.469(3) . ?
C32 C31 1.383(3) . ?
C32 C27 1.399(3) . ?
C32 B2 1.634(3) . ?
C37 C36 1.373(3) . ?
C33 C34 1.383(3) . ?
C36 C35 1.375(3) . ?
C27 C28 1.376(3) . ?
C35 C34 1.376(3) . ?
C31 C30 1.375(3) . ?
C25 C20 1.385(3) . ?
C25 C24 1.390(3) . ?
C28 C29 1.374(3) . ?
C30 C29 1.375(3) . ?
C20 C21 1.383(3) . ?
C24 C23 1.380(3) . ?
C23 C22 1.366(4) . ?
C22 C21 1.378(4) . ?
F1 C8 1.359(2) . ?
F2 C9 1.349(2) . ?
F5 C12 1.342(2) . ?
F4 C11 1.337(2) . ?
O1 C7 1.320(2) . ?
O1 B1 1.487(2) . ?
F3 C10 1.337(2) . ?
F6 C14 1.342(3) . ?
N2 N1 1.464(2) . ?
N2 B1 1.621(2) . ?
N1 C7 1.290(2) . ?
F10 C18 1.363(2) . ?
F7 C15 1.349(2) . ?
C13 C12 1.380(3) . ?
C13 C8 1.388(3) . ?
C13 B1 1.617(3) . ?
C8 C9 1.371(3) . ?
C7 C6 1.467(3) . ?
C12 C11 1.385(3) . ?
F8 C16 1.339(3) . ?
F9 C17 1.333(3) . ?
C10 C9 1.376(3) . ?
C10 C11 1.377(3) . ?
C6 C5 1.381(3) . ?
C6 C1 1.396(3) . ?
C1 C2 1.384(3) . ?
C18 C17 1.382(3) . ?
C18 C19 1.384(3) . ?
B1 C19 1.626(3) . ?
C19 C14 1.387(3) . ?
C14 C15 1.382(3) . ?
C2 C3 1.378(3) . ?
C15 C16 1.368(4) . ?
C5 C4 1.384(3) . ?
C17 C16 1.373(3) . ?
C3 C4 1.379(3) . ?

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
C26 O2 B2 109.56(14) . . ?
N3 N4 B2 107.15(14) . . ?
C33 C38 C37 114.81(17) . . ?
C33 C38 B2 126.11(17) . . ?
C37 C38 B2 118.92(17) . . ?
C26 N3 N4 105.05(14) . . ?
N3 C26 O2 119.77(16) . . ?
N3 C26 C25 122.41(16) . . ?
O2 C26 C25 117.82(17) . . ?
C31 C32 C27 113.93(17) . . ?
C31 C32 B2 127.63(17) . . ?
C27 C32 B2 118.39(17) . . ?
F20 C37 C36 117.94(17) . . ?
F20 C37 C38 118.34(16) . . ?
C36 C37 C38 123.72(18) . . ?
F16 C33 C38 120.44(17) . . ?
F16 C33 C34 116.47(18) . . ?
C38 C33 C34 123.07(18) . . ?
F19 C36 C37 121.06(19) . . ?
F19 C36 C35 119.55(17) . . ?
C37 C36 C35 119.39(18) . . ?
F11 C27 C28 117.45(18) . . ?
F11 C27 C32 119.08(17) . . ?
C28 C27 C32 123.5(2) . . ?
F18 C35 C36 120.19(19) . . ?
F18 C35 C34 120.61(19) . . ?
C36 C35 C34 119.19(18) . . ?
F15 C31 C30 115.73(19) . . ?
F15 C31 C32 119.90(17) . . ?
C30 C31 C32 124.37(19) . . ?
C20 C25 C24 118.98(19) . . ?
C20 C25 C26 120.33(18) . . ?
C24 C25 C26 120.69(19) . . ?
F17 C34 C35 119.46(18) . . ?
F17 C34 C33 120.75(18) . . ?
C35 C34 C33 119.77(19) . . ?
O2 B2 N4 98.41(14) . . ?
O2 B2 C38 114.01(16) . . ?
N4 B2 C38 109.93(14) . . ?
O2 B2 C32 111.09(15) . . ?
N4 B2 C32 112.75(16) . . ?
C38 B2 C32 110.23(15) . . ?
F12 C28 C29 119.34(19) . . ?
F12 C28 C27 121.1(2) . . ?
C29 C28 C27 119.61(19) . . ?
F14 C30 C29 119.90(19) . . ?
F14 C30 C31 120.9(2) . . ?
C29 C30 C31 119.1(2) . . ?
F13 C29 C28 120.3(2) . . ?
F13 C29 C30 120.2(2) . . ?
C28 C29 C30 119.50(19) . . ?
C21 C20 C25 120.0(2) . . ?
C23 C24 C25 120.3(2) . . ?
C22 C23 C24 120.5(2) . . ?
C23 C22 C21 119.8(2) . . ?
C22 C21 C20 120.5(2) . . ?
C7 O1 B1 109.71(14) . . ?
N1 N2 B1 106.72(13) . . ?
C7 N1 N2 105.48(14) . . ?
C12 C13 C8 114.78(17) . . ?
C12 C13 B1 126.58(16) . . ?
C8 C13 B1 118.63(17) . . ?
F1 C8 C9 117.41(16) . . ?
F1 C8 C13 118.46(16) . . ?
C9 C8 C13 124.14(18) . . ?
N1 C7 O1 119.68(16) . . ?
N1 C7 C6 121.72(16) . . ?
O1 C7 C6 118.57(15) . . ?
F5 C12 C13 120.78(17) . . ?
F5 C12 C11 116.17(17) . . ?
C13 C12 C11 123.05(17) . . ?
F3 C10 C9 120.11(18) . . ?
F3 C10 C11 120.29(19) . . ?
C9 C10 C11 119.60(18) . . ?
F2 C9 C8 121.15(18) . . ?
F2 C9 C10 119.91(17) . . ?
C8 C9 C10 118.94(17) . . ?
C5 C6 C1 120.03(18) . . ?
C5 C6 C7 120.16(17) . . ?
C1 C6 C7 119.78(17) . . ?
C2 C1 C6 119.5(2) . . ?
F10 C18 C17 115.5(2) . . ?
F10 C18 C19 120.27(18) . . ?
C17 C18 C19 124.24(19) . . ?
O1 B1 C13 113.49(16) . . ?
O1 B1 N2 98.15(13) . . ?
C13 B1 N2 108.51(14) . . ?
O1 B1 C19 110.73(15) . . ?
C13 B1 C19 112.10(15) . . ?
N2 B1 C19 113.13(16) . . ?
F4 C11 C10 120.06(18) . . ?
F4 C11 C12 120.47(18) . . ?
C10 C11 C12 119.47(18) . . ?
C18 C19 C14 114.32(18) . . ?
C18 C19 B1 127.17(16) . . ?
C14 C19 B1 118.50(18) . . ?
F6 C14 C15 117.45(17) . . ?
F6 C14 C19 119.22(19) . . ?
C15 C14 C19 123.3(2) . . ?
C3 C2 C1 120.2(2) . . ?
F7 C15 C16 119.8(2) . . ?
F7 C15 C14 120.6(2) . . ?
C16 C15 C14 119.55(19) . . ?
C6 C5 C4 119.7(2) . . ?
F9 C17 C16 120.4(2) . . ?
F9 C17 C18 121.0(2) . . ?
C16 C17 C18 118.6(2) . . ?
F8 C16 C15 119.9(2) . . ?
F8 C16 C17 120.2(2) . . ?
C15 C16 C17 119.9(2) . . ?
C2 C3 C4 120.1(2) . . ?
C3 C4 C5 120.4(2) . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_rm_1909b
_database_code_depnum_ccdc_archive 'CCDC 1903201'
loop_
_audit_author_name
_audit_author_address
'Theo Gazis'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-03-14 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;
# end Validation Reply Form
_audit_creation_date             2019-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1.33(C25 H8 B F15 N2 O)'
_chemical_formula_sum            'C33.33 H10.67 B1.33 F20 N2.67 O1.33'
_chemical_formula_weight         864.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H8 N2 B O F15'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8497(5)
_cell_length_b                   16.1722(8)
_cell_length_c                   13.6947(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.795(5)
_cell_angle_gamma                90
_cell_volume                     2323.27(19)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    5987
_cell_measurement_temperature    199.97(13)
_cell_measurement_theta_max      29.4300
_cell_measurement_theta_min      4.0550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
15 -3 1 0.1356
-15 3 -1 0.1332
2 -15 -15 0.0560
1 4 18 0.0880
4 -19 7 0.1175
-9 -15 11 0.1434
9 19 -3 0.1091
-2 -17 13 0.0916
-4 2 19 0.0767
-12 14 3 0.1358
7 7 -18 0.1481
-4 10 17 0.0803
-14 9 1 0.1126
-15 -1 1 0.1368
0 -19 10 0.0895
7 -15 -14 0.0865
15 0 -4 0.1418

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.164
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
14.9812 -3.0010 0.9999 -1.0051 -0.0709 0.2387
-14.9812 3.0010 -0.9999 1.0051 0.0709 -0.2387
1.9933 -14.9890 -14.9771 -0.2197 0.2969 -0.9499
1.0040 4.0012 17.9736 -0.1242 0.1472 0.9784
3.9973 -18.9779 6.9913 -0.5291 0.8155 0.1219
-8.9850 -14.9770 10.9842 0.3297 0.9079 0.1802
8.9873 18.9752 -2.9961 -0.3294 -0.9237 0.2818
-1.9933 -16.9762 12.9820 -0.1559 0.9256 0.3592
-3.9893 2.0053 18.9719 0.1665 0.3123 0.9197
-11.9840 13.9892 2.9938 0.9217 -0.3321 0.1772
6.9856 6.9841 -17.9737 -0.2560 -0.6897 -0.6847
-3.9900 9.9958 16.9743 0.2754 -0.0375 0.9421
-13.9820 8.9947 0.9969 1.0016 -0.1434 -0.0309
-14.9805 -0.9939 0.9974 0.9446 0.2634 -0.1999
0.0033 -18.9756 9.9866 -0.2904 0.9236 0.2096
6.9872 -14.9902 -13.9781 -0.5466 0.2458 -0.8216
14.9796 -0.0059 -3.9930 -0.9387 -0.2772 0.0343

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12738
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.708
_diffrn_reflns_theta_min         3.311
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.97(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  29.00   1.00   27.61    --  -11.05 -99.00 150.00   47
  2  ω    -89.00 -44.00   1.00   27.61    --  -11.05 -19.00 -90.00   45
  3  ω    -28.00   1.00   1.00   27.61    --  -11.05 -19.00 -90.00   29
  4  ω    -22.00  62.00   1.00   27.61    --  -11.05  57.00  60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0642621000
_diffrn_orient_matrix_UB_12      0.0121244000
_diffrn_orient_matrix_UB_13      -0.0060198000
_diffrn_orient_matrix_UB_21      -0.0137948000
_diffrn_orient_matrix_UB_22      -0.0393501000
_diffrn_orient_matrix_UB_23      0.0177210000
_diffrn_orient_matrix_UB_31      0.0156622000
_diffrn_orient_matrix_UB_32      0.0153492000
_diffrn_orient_matrix_UB_33      0.0501454000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4571
_reflns_number_total             5617
_reflns_odcompleteness_completeness 99.64
_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 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.026
_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)+(0.0556P)²+0.9515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H22(0.034) H27(0.039) H41(0.043) H44(0.055)
 Fixed X: H22(1.109864) H27(1.138684) H41(1.3132) H44(1.510911)
 Fixed Y: H22(0.034618) H27(0.244485) H41(0.329417) H44(0.137548)
 Fixed Z: H22(0.284966) H27(0.44996) H41(0.460059) H44(0.396066)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.56213(9) 0.02608(7) 0.28829(8) 0.0355(2) Uani 1 1 d . . . . .
F2 F 0.62304(9) 0.06703(7) 0.10789(7) 0.0357(2) Uani 1 1 d . . . . .
F3 F 0.87287(11) 0.15757(6) 0.15915(7) 0.0371(2) Uani 1 1 d . . . . .
F4 F 0.76672(10) 0.05550(7) 0.45089(7) 0.0361(2) Uani 1 1 d . . . . .
F5 F 1.00838(10) -0.08171(7) 0.15599(7) 0.0385(3) Uani 1 1 d . . . . .
F6 F 0.96029(11) -0.10429(7) -0.04245(8) 0.0441(3) Uani 1 1 d . . . . .
O7 O 1.05315(11) 0.08680(8) 0.48026(8) 0.0298(3) Uani 1 1 d . . . . .
F8 F 0.74078(11) 0.20987(8) 0.50852(8) 0.0458(3) Uani 1 1 d . . . . .
F9 F 0.58205(11) 0.04953(7) -0.08979(8) 0.0428(3) Uani 1 1 d . . . . .
F10 F 0.84306(11) 0.31036(7) 0.21708(8) 0.0426(3) Uani 1 1 d . . . . .
F11 F 0.88038(10) -0.17522(6) 0.29076(8) 0.0382(2) Uani 1 1 d . . . . .
N12 N 0.97186(12) -0.02299(9) 0.33244(10) 0.0256(3) Uani 1 1 d . . . . .
F13 F 0.40743(10) -0.09218(8) 0.31672(9) 0.0467(3) Uani 1 1 d . . . . .
F14 F 0.77638(12) 0.33933(7) 0.39261(10) 0.0493(3) Uani 1 1 d . . . . .
F15 F 0.72404(12) -0.29147(7) 0.32249(9) 0.0468(3) Uani 1 1 d . . . . .
C16 C 0.81654(15) -0.00787(10) 0.14276(11) 0.0247(3) Uani 1 1 d . . . . .
F17 F 0.75176(12) -0.03502(7) -0.16923(7) 0.0459(3) Uani 1 1 d . . . . .
F18 F 0.48212(11) -0.25313(8) 0.33008(9) 0.0508(3) Uani 1 1 d . . . . .
C19 C 0.81221(14) 0.09756(10) 0.29817(11) 0.0256(3) Uani 1 1 d . . . . .
C20 C 1.21992(15) 0.14011(11) 0.41355(11) 0.0270(3) Uani 1 1 d . . . . .
C21 C 0.73218(15) -0.06700(10) 0.29074(11) 0.0259(3) Uani 1 1 d . . . . .
N22 N 1.07290(12) 0.03363(9) 0.33353(10) 0.0281(3) Uani 1 1 d . . . . .
H22 H 1.109864 0.034618 0.284966 0.034 Uiso 1 1 calc R . . . .
C23 C 1.10928(14) 0.08602(10) 0.41336(11) 0.0261(3) Uani 1 1 d . . . . .
C24 C 0.89780(16) -0.04975(10) 0.09822(12) 0.0277(3) Uani 1 1 d . . . . .
C25 C 0.82362(16) 0.24704(11) 0.27432(13) 0.0316(4) Uani 1 1 d . . . . .
C26 C 0.68552(16) 0.01479(11) -0.02905(12) 0.0306(4) Uani 1 1 d . . . . .
C27 C 1.21313(16) 0.22309(11) 0.43817(13) 0.0329(4) Uani 1 1 d . . . . .
H27 H 1.138684 0.244485 0.449960 0.039 Uiso 1 1 calc R . . . .
C28 C 0.76383(15) -0.15043(11) 0.29896(12) 0.0289(3) Uani 1 1 d . . . . .
C29 C 0.87710(18) -0.06142(11) -0.00507(13) 0.0318(4) Uani 1 1 d . . . . .
C30 C 0.68435(18) -0.21287(11) 0.31415(13) 0.0343(4) Uani 1 1 d . . . . .
C31 C 0.77049(16) 0.19637(12) 0.42083(13) 0.0322(4) Uani 1 1 d . . . . .
C32 C 0.56260(17) -0.19342(12) 0.31899(13) 0.0364(4) Uani 1 1 d . . . . .
C33 C 0.70917(15) 0.02345(10) 0.07439(12) 0.0274(3) Uani 1 1 d . . . . .
C34 C 0.83514(15) 0.16628(10) 0.24508(12) 0.0280(3) Uani 1 1 d . . . . .
C35 C 0.78280(15) 0.11690(11) 0.38850(12) 0.0278(3) Uani 1 1 d . . . . .
C36 C 0.60861(15) -0.05142(11) 0.29712(12) 0.0289(3) Uani 1 1 d . . . . .
B37 B 0.82923(16) 0.00237(11) 0.26401(12) 0.0240(3) Uani 1 1 d . . . . .
C38 C 0.78986(16) 0.26197(11) 0.36301(14) 0.0342(4) Uani 1 1 d . . . . .
C39 C 0.77065(18) -0.02764(11) -0.06894(12) 0.0327(4) Uani 1 1 d . . . . .
C40 C 1.33052(16) 0.10819(12) 0.39665(15) 0.0366(4) Uani 1 1 d . . . . .
C41 C 1.31790(18) 0.27361(12) 0.44502(14) 0.0361(4) Uani 1 1 d . . . . .
H41 H 1.313200 0.329417 0.460059 0.043 Uiso 1 1 calc R . . . .
C42 C 0.52517(16) -0.11217(12) 0.31115(13) 0.0338(4) Uani 1 1 d . . . . .
C43 C 1.42926(18) 0.24164(13) 0.42965(14) 0.0382(4) Uani 1 1 d . . . . .
C44 C 1.43557(18) 0.15915(14) 0.40592(17) 0.0458(5) Uani 1 1 d . . . . .
H44 H 1.510911 0.137548 0.396066 0.055 Uiso 1 1 calc R . . . .
H12A H 0.967(2) -0.0278(13) 0.3959(17) 0.038(5) Uiso 1 1 d . . . . .
H12B H 1.0006(18) -0.0746(14) 0.3171(15) 0.032(5) Uiso 1 1 d . . . . .
H43 H 1.505(2) 0.2774(15) 0.4368(16) 0.044(6) Uiso 1 1 d . . . . .
H40 H 1.335(2) 0.0500(15) 0.3799(17) 0.047(6) 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
F1 C36 1.345(2) . ?
F2 C33 1.3414(19) . ?
F3 C34 1.3484(18) . ?
F4 C35 1.350(2) . ?
F5 C24 1.3593(19) . ?
F6 C29 1.339(2) . ?
O7 C23 1.2228(19) . ?
F8 C31 1.3385(19) . ?
F9 C26 1.338(2) . ?
F10 C25 1.339(2) . ?
F11 C28 1.3582(19) . ?
N12 N22 1.4255(19) . ?
N12 B37 1.643(2) . ?
F13 C42 1.339(2) . ?
F14 C38 1.335(2) . ?
F15 C30 1.338(2) . ?
C16 C24 1.372(2) . ?
C16 C33 1.390(2) . ?
C16 B37 1.639(2) . ?
F17 C39 1.3412(18) . ?
F18 C32 1.336(2) . ?
C19 C34 1.385(2) . ?
C19 C35 1.390(2) . ?
C19 B37 1.633(2) . ?
C20 C23 1.485(2) . ?
C20 C27 1.390(2) . ?
C20 C40 1.379(2) . ?
C21 C28 1.390(2) . ?
C21 C36 1.389(2) . ?
C21 B37 1.643(2) . ?
N22 C23 1.360(2) . ?
C24 C29 1.387(2) . ?
C25 C34 1.381(2) . ?
C25 C38 1.377(3) . ?
C26 C33 1.381(2) . ?
C26 C39 1.371(3) . ?
C27 C41 1.384(3) . ?
C28 C30 1.378(2) . ?
C29 C39 1.372(3) . ?
C30 C32 1.376(3) . ?
C31 C35 1.377(2) . ?
C31 C38 1.372(3) . ?
C32 C42 1.371(3) . ?
C36 C42 1.382(2) . ?
C40 C44 1.386(3) . ?
C41 C43 1.379(3) . ?
C43 C44 1.379(3) . ?

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
N22 N12 B37 117.09(12) . . ?
C24 C16 C33 113.79(14) . . ?
C24 C16 B37 127.08(14) . . ?
C33 C16 B37 118.98(14) . . ?
C34 C19 C35 113.54(15) . . ?
C34 C19 B37 123.88(14) . . ?
C35 C19 B37 122.39(14) . . ?
C27 C20 C23 118.44(15) . . ?
C40 C20 C23 121.12(16) . . ?
C40 C20 C27 120.29(16) . . ?
C28 C21 B37 121.46(14) . . ?
C36 C21 C28 113.19(15) . . ?
C36 C21 B37 125.04(15) . . ?
C23 N22 N12 118.25(13) . . ?
O7 C23 C20 123.34(14) . . ?
O7 C23 N22 120.73(15) . . ?
N22 C23 C20 115.92(13) . . ?
F5 C24 C16 120.05(13) . . ?
F5 C24 C29 115.52(14) . . ?
C16 C24 C29 124.42(15) . . ?
F10 C25 C34 120.94(15) . . ?
F10 C25 C38 119.98(15) . . ?
C38 C25 C34 119.07(16) . . ?
F9 C26 C33 120.12(16) . . ?
F9 C26 C39 120.40(15) . . ?
C39 C26 C33 119.46(16) . . ?
C41 C27 C20 119.54(16) . . ?
F11 C28 C21 119.74(15) . . ?
F11 C28 C30 115.33(15) . . ?
C30 C28 C21 124.93(16) . . ?
F6 C29 C24 120.71(16) . . ?
F6 C29 C39 120.16(15) . . ?
C39 C29 C24 119.13(15) . . ?
F15 C30 C28 120.61(17) . . ?
F15 C30 C32 120.35(16) . . ?
C32 C30 C28 119.04(17) . . ?
F8 C31 C35 120.40(17) . . ?
F8 C31 C38 119.96(16) . . ?
C38 C31 C35 119.64(15) . . ?
F18 C32 C30 120.24(18) . . ?
F18 C32 C42 120.81(17) . . ?
C42 C32 C30 118.95(16) . . ?
F2 C33 C16 119.88(13) . . ?
F2 C33 C26 116.16(14) . . ?
C26 C33 C16 123.93(15) . . ?
F3 C34 C19 120.63(14) . . ?
F3 C34 C25 114.96(15) . . ?
C25 C34 C19 124.40(15) . . ?
F4 C35 C19 119.59(15) . . ?
F4 C35 C31 116.38(14) . . ?
C31 C35 C19 124.02(16) . . ?
F1 C36 C21 120.62(15) . . ?
F1 C36 C42 115.54(15) . . ?
C42 C36 C21 123.84(16) . . ?
C16 B37 N12 112.07(12) . . ?
C16 B37 C21 105.30(12) . . ?
C19 B37 N12 103.34(12) . . ?
C19 B37 C16 113.52(13) . . ?
C19 B37 C21 117.01(13) . . ?
C21 B37 N12 105.45(12) . . ?
F14 C38 C25 120.46(17) . . ?
F14 C38 C31 120.32(16) . . ?
C31 C38 C25 119.22(16) . . ?
F17 C39 C26 120.67(16) . . ?
F17 C39 C29 120.08(16) . . ?
C26 C39 C29 119.24(14) . . ?
C20 C40 C44 119.50(17) . . ?
C43 C41 C27 120.33(17) . . ?
F13 C42 C32 119.66(16) . . ?
F13 C42 C36 120.31(17) . . ?
C32 C42 C36 120.04(16) . . ?
C41 C43 C44 119.80(17) . . ?
C43 C44 C40 120.52(17) . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.410
_oxdiff_exptl_absorpt_empirical_full_min 0.817
# start Validation Reply Form
_vrf_PLAT910_rm_1909b            
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         10 Note  
RESPONSE: A small number of reflections were obscured by the beamstop
;
####################################################################### 
# 
# 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_RM1846b
_database_code_depnum_ccdc_archive 'CCDC 1897210'
loop_
_audit_author_name
_audit_author_address
'Theo Gazis'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-14 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_RM1846b             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.904 Why?  
RESPONSE: Acknowledged. The automated data collection strategy was not checked.
          Nevertheless including additional high angle data to theta_max the
          total number of unique reflections (5276, 4265 with I > 2s(I))
          was adequate for refinement with a final data:parameter ratio of 15:1.
;
_vrf_PLAT260_RM1846b             
;
PROBLEM: Large Average Ueq of Residue Including      Cl1S      0.284 Check 
RESPONSE: This is a disordered solvent molecule located on a special position.
          It is possible that the sof of the solvent molecule is less than 1.0
;
_vrf_PLAT910_RM1846b             
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note  
RESPONSE: A small number of reflections were obscured by the beamstop.
;
_vrf_PLAT911_RM1846b             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        434 Report
RESPONSE: No reflections were omitted from the data which used an automated 
          data collection strategy. Despite missing reflections the total
          5276 unique reflections were adequate for structure refinement
          with just 364 parameters, this afforded a data:parameter ratio of
          almost 15:1. 
;
# end Validation Reply Form 
_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H13 B F9 N2 O, 0.5 (C H2 Cl2)'
_chemical_formula_sum            'C25.50 H14 B Cl F9 N2 O'
_chemical_formula_weight         581.65

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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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                   25.9971(10)
_cell_length_b                   15.1972(6)
_cell_length_c                   13.0295(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.668(3)
_cell_angle_gamma                90
_cell_volume                     5130.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5956
_cell_measurement_theta_min      4.072
_cell_measurement_theta_max      29.220

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             2336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.368
_exptl_crystal_size_min          0.161
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.382
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  
'Agilent Supernova Dual Atlas with CCD Detector'
_diffrn_measurement_method       'Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11177
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.393
_diffrn_reflns_theta_max         29.763
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.721
_diffrn_measured_fraction_theta_full 0.904
_diffrn_reflns_Laue_measured_fraction_max 0.721
_diffrn_reflns_Laue_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.721
_diffrn_reflns_point_group_measured_fraction_full 0.904
_reflns_number_total             5276
_reflns_number_gt                4265
_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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'XSHELL and Mercury'
_computing_publication_material  XCIF
_refine_special_details          
;
structure solved by direct methods. H atoms added at calculated positions
and refined with a riding model except NH2 group where the H atoms were located 
in the difference map and freely refined.
A dichloromethne solvent molecule was identified and located on
a special position. The C atom was modelled over two sites with common Uiso for the C
atom and riding H atoms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0906P)²+8.1701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5276
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1790
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
N1 N 0.20713(7) 0.22920(14) 0.14145(15) 0.0314(4) Uani 1 1 d . . . . .
H1A H 0.2168(11) 0.284(2) 0.144(2) 0.040(7) Uiso 1 1 d . . . . .
H1B H 0.1940(10) 0.2182(17) 0.076(2) 0.035(7) Uiso 1 1 d . . . . .
N2 N 0.25205(7) 0.17548(13) 0.16006(15) 0.0352(4) Uani 1 1 d . . . . .
O1 O 0.29673(6) 0.27629(11) 0.07751(12) 0.0361(4) Uani 1 1 d . . . . .
C10 C 0.29648(8) 0.20641(16) 0.12443(16) 0.0317(5) Uani 1 1 d . . . . .
C11 C 0.34250(9) 0.14984(17) 0.14431(18) 0.0364(5) Uani 1 1 d . . . . .
C12 C 0.39078(10) 0.1891(2) 0.1497(2) 0.0474(6) Uani 1 1 d . . . . .
H12 H 0.393716 0.249594 0.141182 0.057 Uiso 1 1 calc R U . . .
C13 C 0.43453(11) 0.1379(3) 0.1677(3) 0.0635(9) Uani 1 1 d . . . . .
H13 H 0.466930 0.164219 0.172350 0.076 Uiso 1 1 calc R U . . .
C14 C 0.43040(12) 0.0484(3) 0.1787(3) 0.0669(9) Uani 1 1 d . . . . .
H14 H 0.460018 0.014657 0.192001 0.080 Uiso 1 1 calc R U . . .
C15 C 0.38259(13) 0.0082(2) 0.1704(3) 0.0609(8) Uani 1 1 d . . . . .
H15 H 0.380089 -0.052703 0.175485 0.073 Uiso 1 1 calc R U . . .
C16 C 0.33855(11) 0.05877(19) 0.1543(2) 0.0473(6) Uani 1 1 d . . . . .
H16 H 0.306244 0.032119 0.150174 0.057 Uiso 1 1 calc R U . . .
B1 B 0.16189(9) 0.21129(18) 0.21900(18) 0.0303(5) Uani 1 1 d . . . . .
C21 C 0.11118(8) 0.26391(16) 0.16583(17) 0.0338(5) Uani 1 1 d . . . . .
F22 F 0.05175(6) 0.15005(12) 0.19038(15) 0.0586(5) Uani 1 1 d . . . . .
C22 C 0.06119(9) 0.23220(18) 0.1561(2) 0.0426(6) Uani 1 1 d . . . . .
C23 C 0.01852(10) 0.2778(2) 0.1134(2) 0.0540(7) Uani 1 1 d . . . . .
H23 H -0.014194 0.252602 0.108173 0.065 Uiso 1 1 calc R U . . .
F24 F -0.01428(8) 0.40632(15) 0.03508(18) 0.0799(6) Uani 1 1 d . . . . .
C24 C 0.02647(11) 0.3610(2) 0.0794(2) 0.0544(7) Uani 1 1 d . . . . .
C25 C 0.07387(12) 0.40006(19) 0.0874(2) 0.0500(7) Uani 1 1 d . . . . .
H25 H 0.078773 0.457350 0.065040 0.060 Uiso 1 1 calc R U . . .
F26 F 0.16169(6) 0.38914(10) 0.13771(13) 0.0508(4) Uani 1 1 d . . . . .
C26 C 0.11410(9) 0.34959(17) 0.13053(19) 0.0393(5) Uani 1 1 d . . . . .
C31 C 0.17736(8) 0.25774(15) 0.33059(17) 0.0328(5) Uani 1 1 d . . . . .
F32 F 0.10167(5) 0.19882(11) 0.39030(12) 0.0471(4) Uani 1 1 d . . . . .
C32 C 0.14390(9) 0.25138(16) 0.40855(19) 0.0371(5) Uani 1 1 d . . . . .
C33 C 0.14949(11) 0.29261(19) 0.5030(2) 0.0471(6) Uani 1 1 d . . . . .
H33 H 0.125595 0.285277 0.551731 0.057 Uiso 1 1 calc R U . . .
F34 F 0.19965(9) 0.38639(14) 0.61370(13) 0.0701(6) Uani 1 1 d . . . . .
C34 C 0.19224(12) 0.34509(19) 0.52138(19) 0.0487(7) Uani 1 1 d . . . . .
C35 C 0.22758(11) 0.35703(19) 0.45079(19) 0.0450(6) Uani 1 1 d . . . . .
H35 H 0.256325 0.392905 0.464240 0.054 Uiso 1 1 calc R U . . .
F36 F 0.25406(6) 0.32774(12) 0.28914(12) 0.0527(4) Uani 1 1 d . . . . .
C36 C 0.21846(9) 0.31304(17) 0.35817(18) 0.0381(5) Uani 1 1 d . . . . .
C41 C 0.15571(8) 0.10397(15) 0.21736(17) 0.0313(5) Uani 1 1 d . . . . .
F42 F 0.13255(6) 0.11120(10) 0.03925(11) 0.0483(4) Uani 1 1 d . . . . .
C42 C 0.14049(9) 0.06072(17) 0.12559(17) 0.0359(5) Uani 1 1 d . . . . .
C43 C 0.13210(10) -0.02802(18) 0.1131(2) 0.0421(6) Uani 1 1 d . . . . .
H43 H 0.121434 -0.052491 0.049461 0.050 Uiso 1 1 calc R U . . .
F44 F 0.13240(8) -0.16608(10) 0.19218(14) 0.0594(5) Uani 1 1 d . . . . .
C44 C 0.14042(10) -0.07824(16) 0.2002(2) 0.0409(6) Uani 1 1 d . . . . .
C45 C 0.15668(9) -0.04423(17) 0.2942(2) 0.0395(5) Uani 1 1 d . . . . .
H45 H 0.162558 -0.079626 0.352156 0.047 Uiso 1 1 calc R U . . .
F46 F 0.18104(6) 0.07734(10) 0.39262(10) 0.0442(4) Uani 1 1 d . . . . .
C46 C 0.16393(8) 0.04582(16) 0.29830(17) 0.0329(5) Uani 1 1 d . . . . .
Cl1S Cl 0.48780(13) 0.3958(3) 0.1381(4) 0.284(2) Uani 1 1 d . . . . .
C1S C 0.500000 0.4563(10) 0.250000 0.099(3) Uiso 0.5 2 d S . P A 1
H1S1 H 0.470536 0.494070 0.258134 0.118 Uiso 0.25 1 calc R U P A 1
H1S2 H 0.529466 0.494065 0.241864 0.118 Uiso 0.25 1 calc R U P A 1
C2S C 0.500000 0.3741(11) 0.250000 0.099(3) Uiso 0.5 2 d S . P A 2
H2S1 H 0.528747 0.334642 0.242063 0.118 Uiso 0.25 1 calc R U P A 2
H2S2 H 0.471259 0.334628 0.257936 0.118 Uiso 0.25 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.429(3) . ?
N1 B1 1.635(3) . ?
N1 H1A 0.87(3) . ?
N1 H1B 0.91(3) . ?
N2 C10 1.363(3) . ?
O1 C10 1.226(3) . ?
C10 C11 1.479(3) . ?
C11 C12 1.386(3) . ?
C11 C16 1.395(4) . ?
C12 C13 1.382(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
B1 C31 1.637(3) . ?
B1 C41 1.639(3) . ?
B1 C21 1.646(3) . ?
C21 C22 1.382(3) . ?
C21 C26 1.385(4) . ?
F22 C22 1.355(3) . ?
C22 C23 1.386(4) . ?
C23 C24 1.361(5) . ?
C23 H23 0.9300 . ?
F24 C24 1.353(3) . ?
C24 C25 1.364(4) . ?
C25 C26 1.379(4) . ?
C25 H25 0.9300 . ?
F26 C26 1.372(3) . ?
C31 C36 1.384(3) . ?
C31 C32 1.393(3) . ?
F32 C32 1.363(3) . ?
C32 C33 1.379(4) . ?
C33 C34 1.373(4) . ?
C33 H33 0.9300 . ?
F34 C34 1.357(3) . ?
C34 C35 1.364(4) . ?
C35 C36 1.383(4) . ?
C35 H35 0.9300 . ?
F36 C36 1.361(3) . ?
C41 C46 1.379(3) . ?
C41 C42 1.393(3) . ?
F42 C42 1.363(3) . ?
C42 C43 1.374(4) . ?
C43 C44 1.371(4) . ?
C43 H43 0.9300 . ?
F44 C44 1.354(3) . ?
C44 C45 1.364(4) . ?
C45 C46 1.382(4) . ?
C45 H45 0.9300 . ?
F46 C46 1.360(3) . ?
Cl1S C2S 1.504(6) . ?
Cl1S C1S 1.731(9) . ?
C1S H1S1 0.9700 . ?
C1S H1S2 0.9700 . ?
C2S H2S1 0.9700 . ?
C2S H2S2 0.9700 . ?

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
N2 N1 B1 114.77(17) . . ?
N2 N1 H1A 108.1(19) . . ?
B1 N1 H1A 110.8(19) . . ?
N2 N1 H1B 107.1(17) . . ?
B1 N1 H1B 108.4(17) . . ?
H1A N1 H1B 107(3) . . ?
C10 N2 N1 116.65(19) . . ?
O1 C10 N2 120.5(2) . . ?
O1 C10 C11 123.7(2) . . ?
N2 C10 C11 115.8(2) . . ?
C12 C11 C16 119.7(2) . . ?
C12 C11 C10 118.3(2) . . ?
C16 C11 C10 121.9(2) . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
N1 B1 C31 109.89(17) . . ?
N1 B1 C41 103.43(17) . . ?
C31 B1 C41 117.24(18) . . ?
N1 B1 C21 104.52(17) . . ?
C31 B1 C21 107.15(19) . . ?
C41 B1 C21 113.82(18) . . ?
C22 C21 C26 111.9(2) . . ?
C22 C21 B1 125.8(2) . . ?
C26 C21 B1 122.2(2) . . ?
F22 C22 C21 119.0(2) . . ?
F22 C22 C23 115.6(2) . . ?
C21 C22 C23 125.4(3) . . ?
C24 C23 C22 117.2(3) . . ?
C24 C23 H23 121.4 . . ?
C22 C23 H23 121.4 . . ?
F24 C24 C23 118.5(3) . . ?
F24 C24 C25 118.8(3) . . ?
C23 C24 C25 122.7(3) . . ?
C24 C25 C26 116.1(3) . . ?
C24 C25 H25 122.0 . . ?
C26 C25 H25 122.0 . . ?
F26 C26 C25 115.7(2) . . ?
F26 C26 C21 117.6(2) . . ?
C25 C26 C21 126.7(2) . . ?
C36 C31 C32 111.6(2) . . ?
C36 C31 B1 128.4(2) . . ?
C32 C31 B1 119.7(2) . . ?
F32 C32 C33 116.6(2) . . ?
F32 C32 C31 117.1(2) . . ?
C33 C32 C31 126.4(2) . . ?
C34 C33 C32 116.4(2) . . ?
C34 C33 H33 121.8 . . ?
C32 C33 H33 121.8 . . ?
F34 C34 C35 118.8(3) . . ?
F34 C34 C33 118.5(3) . . ?
C35 C34 C33 122.7(2) . . ?
C34 C35 C36 116.5(2) . . ?
C34 C35 H35 121.7 . . ?
C36 C35 H35 121.7 . . ?
F36 C36 C35 114.8(2) . . ?
F36 C36 C31 118.7(2) . . ?
C35 C36 C31 126.5(2) . . ?
C46 C41 C42 111.7(2) . . ?
C46 C41 B1 128.2(2) . . ?
C42 C41 B1 120.09(19) . . ?
F42 C42 C43 116.3(2) . . ?
F42 C42 C41 117.1(2) . . ?
C43 C42 C41 126.6(2) . . ?
C44 C43 C42 115.8(2) . . ?
C44 C43 H43 122.1 . . ?
C42 C43 H43 122.1 . . ?
F44 C44 C45 118.5(2) . . ?
F44 C44 C43 118.2(2) . . ?
C45 C44 C43 123.3(2) . . ?
C44 C45 C46 116.2(2) . . ?
C44 C45 H45 121.9 . . ?
C46 C45 H45 121.9 . . ?
F46 C46 C41 119.0(2) . . ?
F46 C46 C45 114.7(2) . . ?
C41 C46 C45 126.3(2) . . ?
Cl1S C1S Cl1S 115.9(10) . 2_655 ?
Cl1S C1S H1S1 108.3 . . ?
Cl1S C1S H1S1 108.3 2_655 . ?
Cl1S C1S H1S2 108.3 . . ?
Cl1S C1S H1S2 108.3 2_655 . ?
H1S1 C1S H1S2 107.4 . . ?
Cl1S C2S Cl1S 154.6(13) . 2_655 ?
Cl1S C2S H2S1 97.8 . . ?
Cl1S C2S H2S1 97.8 2_655 . ?
Cl1S C2S H2S2 97.8 . . ?
Cl1S C2S H2S2 97.8 2_655 . ?
H2S1 C2S H2S2 103.7 . . ?

_refine_diff_density_max         0.862
_refine_diff_density_min         -1.031
_refine_diff_density_rms         0.063

