# Electronic Supplementary Material (ESI) for ChemComm.
# 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_exp_15827
_database_code_depnum_ccdc_archive 'CCDC 1915930'
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;
_audit_creation_date             2019-03-30
_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         'C26 H18 B F2 N3 O'
_chemical_formula_sum            'C26 H18 B F2 N3 O'
_chemical_formula_weight         437.24
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   16.1393(7)
_cell_length_b                   7.0248(4)
_cell_length_c                   37.8519(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.108(5)
_cell_angle_gamma                90
_cell_volume                     4285.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4668
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2190
_cell_measurement_theta_min      4.6700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1115
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            20352
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.962
_diffrn_reflns_theta_min         4.680
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  64.00   1.00    1.00    --   37.66 -77.00 -60.00   94
  2  ω     21.00 105.00   1.00    1.00    --   37.66  57.00-180.00   84
  3  ω     18.00  91.00   1.00    1.00    --   37.66-125.00 -30.00   73
  4  ω    -30.00  64.00   1.00    1.00    --   37.66 -77.00-120.00   94
  5  ω    -32.00  57.00   1.00    1.00    --   37.66 -37.00  60.00   89
  6  ω    -30.00  64.00   1.00    1.00    --   37.66 -77.00 -30.00   94
  7  ω    -30.00  54.00   1.00    1.00    --   37.66 -57.00 150.00   84
  8  ω    -30.00  54.00   1.00    1.00    --   37.66 -57.00-150.00   84
  9  ω     91.00 176.00   1.00    1.00    --  108.00  45.00-120.00   85
 10  ω     91.00 176.00   1.00    1.00    --  108.00  45.00 -60.00   85
 11  ω     41.00 126.00   1.00    1.00    --  108.00 -61.00-180.00   85
 12  ω     39.00 109.00   1.00    1.00    --  108.00 -94.00 -30.00   70
 13  ω     87.00 178.00   1.00    1.00    --  108.00  30.00-150.00   91
 14  ω     39.00 109.00   1.00    1.00    --  108.00 -94.00  60.00   70
 15  ω     40.00 125.00   1.00    1.00    --  108.00 -45.00 -90.00   85
 16  ω     -4.00  77.00   1.00    1.00    --   37.66 -99.00  60.00   81
 17  ω     21.00 105.00   1.00    1.00    --   37.66  57.00   0.00   84
 18  ω      4.00  38.00   1.00    1.00    --   37.66  89.00 -57.00   34
 19  ω     11.00 105.00   1.00    1.00    --   37.66  77.00 -90.00   94
 20  ω     21.00 105.00   1.00    1.00    --   37.66  57.00-120.00   84
 21  ω     11.00 105.00   1.00    1.00    --   37.66  77.00  60.00   94
 22  ω     70.00 178.00   1.00    1.00    --  108.00  15.00  60.00  108
 23  ω     38.00  76.00   1.00    1.00    --  108.00-111.00-120.00   38
 24  ω     91.00 176.00   1.00    1.00    --  108.00  45.00 150.00   85
 25  ω     91.00 176.00   1.00    1.00    --  108.00  45.00 -30.00   85
 26  ω     41.00 126.00   1.00    1.00    --  108.00 -61.00  90.00   85
 27  ω     87.00 178.00   1.00    1.00    --  108.00  30.00 120.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0147466000
_diffrn_orient_matrix_UB_12      -0.0099857000
_diffrn_orient_matrix_UB_13      0.0398367000
_diffrn_orient_matrix_UB_21      -0.0943126000
_diffrn_orient_matrix_UB_22      -0.0109229000
_diffrn_orient_matrix_UB_23      -0.0085475000
_diffrn_orient_matrix_UB_31      0.0054004000
_diffrn_orient_matrix_UB_32      -0.2187351000
_diffrn_orient_matrix_UB_33      -0.0013861000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2819
_reflns_number_total             4167
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.266
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0726
_refine_ls_restrained_S_all      1.042
_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)+(0.1117P)²+1.1755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1812
_refine_ls_wR_factor_ref         0.2108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C12(H12), C14(H14), C16(H16), C19(H19), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
  C32(H32), C33(H33)
;
_atom_sites_solution_hydrogens   geom
_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 0.13440(8) 0.1590(2) 0.31044(4) 0.0635(5) Uani 1 1 d . . . . .
C2 C 0.31667(13) 0.3189(3) 0.33940(6) 0.0448(5) Uani 1 1 d . . . . .
N3 N 0.23491(11) 0.2871(3) 0.27203(5) 0.0469(5) Uani 1 1 d . . . . .
F4 F 0.13111(8) 0.4746(2) 0.29936(4) 0.0652(5) Uani 1 1 d . . . . .
O5 O 0.23576(9) 0.3533(3) 0.33681(4) 0.0596(5) Uani 1 1 d . . . . .
C6 C 0.35955(13) 0.2737(4) 0.30903(6) 0.0456(6) Uani 1 1 d . . . . .
C7 C 0.19569(14) 0.2830(4) 0.23717(6) 0.0462(6) Uani 1 1 d . . . . .
C8 C 0.35825(14) 0.3310(4) 0.37208(6) 0.0476(6) Uani 1 1 d . . . . .
H8 H 0.329254 0.360429 0.391938 0.057 Uiso 1 1 calc R . . . .
N9 N 0.48491(11) 0.3068(3) 0.40797(5) 0.0529(6) Uani 1 1 d . . . . .
C10 C 0.44380(13) 0.2995(3) 0.37553(6) 0.0452(6) Uani 1 1 d . . . . .
C11 C 0.23971(14) 0.3166(4) 0.20762(6) 0.0522(6) Uani 1 1 d . . . . .
H11 H 0.296457 0.339736 0.210178 0.063 Uiso 1 1 calc R . . . .
C12 C 0.31610(14) 0.2613(4) 0.27613(6) 0.0482(6) Uani 1 1 d . . . . .
H12 H 0.345490 0.233790 0.256293 0.058 Uiso 1 1 calc R . . . .
C13 C 0.11612(15) 0.2857(4) 0.17033(7) 0.0514(6) Uani 1 1 d . . . . .
C14 C 0.20049(16) 0.3165(4) 0.17412(7) 0.0567(7) Uani 1 1 d . . . . .
H14 H 0.230936 0.337181 0.154305 0.068 Uiso 1 1 calc R . . . .
C15 C 0.44070(14) 0.3142(4) 0.44015(6) 0.0556(7) Uani 1 1 d . . . . .
C16 C 0.44588(14) 0.2444(4) 0.31299(6) 0.0529(6) Uani 1 1 d . . . . .
H16 H 0.475051 0.215588 0.293148 0.063 Uiso 1 1 calc R . . . .
C17 C 0.07370(16) 0.2947(4) 0.13604(7) 0.0578(7) Uani 1 1 d . . . . .
B18 B 0.18176(15) 0.3197(5) 0.30551(7) 0.0507(7) Uani 1 1 d . . . . .
C19 C 0.48769(13) 0.2573(4) 0.34507(6) 0.0515(6) Uani 1 1 d . . . . .
H19 H 0.544792 0.238472 0.347001 0.062 Uiso 1 1 calc R . . . .
N20 N 0.04061(16) 0.3055(4) 0.10869(6) 0.0732(7) Uani 1 1 d . . . . .
C21 C 0.57412(14) 0.2995(4) 0.41250(6) 0.0516(6) Uani 1 1 d . . . . .
C22 C 0.07137(16) 0.2497(4) 0.19958(7) 0.0633(7) Uani 1 1 d . . . . .
H22 H 0.014613 0.226783 0.196979 0.076 Uiso 1 1 calc R . . . .
C23 C 0.11145(15) 0.2478(5) 0.23296(7) 0.0631(7) Uani 1 1 d . . . . .
H23 H 0.081337 0.222674 0.252694 0.076 Uiso 1 1 calc R . . . .
C24 C 0.70616(17) 0.4464(5) 0.41005(8) 0.0740(9) Uani 1 1 d . . . . .
H24 H 0.738297 0.550739 0.404343 0.089 Uiso 1 1 calc R . . . .
C25 C 0.62046(15) 0.4536(4) 0.40394(7) 0.0638(7) Uani 1 1 d . . . . .
H25 H 0.595125 0.561722 0.394165 0.077 Uiso 1 1 calc R . . . .
C26 C 0.69693(18) 0.1341(5) 0.43246(9) 0.0806(10) Uani 1 1 d . . . . .
H26 H 0.722531 0.025971 0.442129 0.097 Uiso 1 1 calc R . . . .
C27 C 0.61162(17) 0.1382(5) 0.42640(8) 0.0697(8) Uani 1 1 d . . . . .
H27 H 0.579840 0.032550 0.431681 0.084 Uiso 1 1 calc R . . . .
C28 C 0.43276(17) 0.4847(5) 0.45728(7) 0.0687(8) Uani 1 1 d . . . . .
H28 H 0.454686 0.596121 0.448344 0.082 Uiso 1 1 calc R . . . .
C29 C 0.4085(2) 0.1520(5) 0.45350(8) 0.0793(9) Uani 1 1 d . . . . .
H29 H 0.414099 0.037161 0.441626 0.095 Uiso 1 1 calc R . . . .
C30 C 0.3591(2) 0.3234(7) 0.50191(8) 0.0929(13) Uani 1 1 d . . . . .
H30 H 0.331751 0.326157 0.522895 0.111 Uiso 1 1 calc R . . . .
C31 C 0.74350(17) 0.2881(5) 0.42430(8) 0.0748(9) Uani 1 1 d . . . . .
H31 H 0.800806 0.285203 0.428456 0.090 Uiso 1 1 calc R . . . .
C32 C 0.39041(19) 0.4858(6) 0.48881(8) 0.0848(11) Uani 1 1 d . . . . .
H32 H 0.383820 0.599877 0.500806 0.102 Uiso 1 1 calc R . . . .
C33 C 0.3677(2) 0.1571(7) 0.48449(10) 0.1027(13) Uani 1 1 d . . . . .
H33 H 0.345980 0.045717 0.493494 0.123 Uiso 1 1 calc R . . . .


_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 B18 1.382(3) . ?
C2 O5 1.326(3) . ?
C2 C6 1.410(3) . ?
C2 C8 1.378(3) . ?
N3 C7 1.433(3) . ?
N3 C12 1.323(3) . ?
N3 B18 1.585(3) . ?
F4 B18 1.373(3) . ?
O5 B18 1.451(3) . ?
C6 C12 1.398(3) . ?
C6 C16 1.408(3) . ?
C7 C11 1.378(3) . ?
C7 C23 1.382(3) . ?
C8 C10 1.398(3) . ?
N9 C10 1.365(3) . ?
N9 C15 1.446(3) . ?
N9 C21 1.442(3) . ?
C10 C19 1.417(3) . ?
C11 C14 1.386(3) . ?
C13 C14 1.379(3) . ?
C13 C17 1.436(3) . ?
C13 C22 1.378(4) . ?
C15 C28 1.371(4) . ?
C15 C29 1.361(4) . ?
C16 C19 1.360(3) . ?
C17 N20 1.141(3) . ?
C21 C25 1.364(4) . ?
C21 C27 1.376(4) . ?
C22 C23 1.388(3) . ?
C24 C25 1.391(3) . ?
C24 C31 1.362(4) . ?
C26 C27 1.384(4) . ?
C26 C31 1.363(5) . ?
C28 C32 1.407(4) . ?
C29 C33 1.376(5) . ?
C30 C32 1.352(5) . ?
C30 C33 1.352(5) . ?

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
O5 C2 C6 120.37(19) . . ?
O5 C2 C8 119.0(2) . . ?
C8 C2 C6 120.6(2) . . ?
C7 N3 B18 120.54(18) . . ?
C12 N3 C7 119.4(2) . . ?
C12 N3 B18 120.09(18) . . ?
C2 O5 B18 125.17(19) . . ?
C12 C6 C2 119.7(2) . . ?
C12 C6 C16 122.1(2) . . ?
C16 C6 C2 118.2(2) . . ?
C11 C7 N3 121.5(2) . . ?
C11 C7 C23 119.0(2) . . ?
C23 C7 N3 119.5(2) . . ?
C2 C8 C10 120.3(2) . . ?
C10 N9 C15 121.43(19) . . ?
C10 N9 C21 122.65(19) . . ?
C21 N9 C15 115.87(17) . . ?
C8 C10 C19 119.5(2) . . ?
N9 C10 C8 120.5(2) . . ?
N9 C10 C19 120.0(2) . . ?
C7 C11 C14 120.8(2) . . ?
N3 C12 C6 122.8(2) . . ?
C14 C13 C17 120.5(2) . . ?
C22 C13 C14 120.2(2) . . ?
C22 C13 C17 119.3(2) . . ?
C13 C14 C11 119.6(2) . . ?
C28 C15 N9 119.5(3) . . ?
C29 C15 N9 119.9(3) . . ?
C29 C15 C28 120.6(3) . . ?
C19 C16 C6 121.7(2) . . ?
N20 C17 C13 178.6(3) . . ?
F1 B18 N3 108.5(2) . . ?
F1 B18 O5 109.6(2) . . ?
F4 B18 F1 109.98(19) . . ?
F4 B18 N3 108.8(2) . . ?
F4 B18 O5 109.6(2) . . ?
O5 B18 N3 110.42(18) . . ?
C16 C19 C10 119.7(2) . . ?
C25 C21 N9 120.0(2) . . ?
C25 C21 C27 120.6(2) . . ?
C27 C21 N9 119.4(2) . . ?
C13 C22 C23 119.6(2) . . ?
C7 C23 C22 120.7(3) . . ?
C31 C24 C25 120.7(3) . . ?
C21 C25 C24 119.0(3) . . ?
C31 C26 C27 120.1(3) . . ?
C21 C27 C26 119.6(3) . . ?
C15 C28 C32 117.9(3) . . ?
C15 C29 C33 120.3(3) . . ?
C33 C30 C32 120.0(3) . . ?
C24 C31 C26 120.0(3) . . ?
C30 C32 C28 121.0(3) . . ?
C30 C33 C29 120.3(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.684
_oxdiff_exptl_absorpt_empirical_full_min 0.535
####################################################################### 
# 
# 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_exp_15939
_database_code_depnum_ccdc_archive 'CCDC 1915931'
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;
_audit_creation_date             2019-02-27
_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         'C17 H19 B F2 N2 O'
_chemical_formula_sum            'C17 H19 B F2 N2 O'
_chemical_formula_weight         316.15
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   6.3794(2)
_cell_length_b                   17.4457(5)
_cell_length_c                   13.9241(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.880(3)
_cell_angle_gamma                90
_cell_volume                     1547.70(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6426
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9250
_cell_measurement_theta_min      4.0250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14733
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.013
_diffrn_reflns_theta_min         5.988
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  54.00   1.00    1.00    --   37.66 -57.00-120.00   84
  2  ω     18.00  91.00   1.00    1.00    --   37.66-125.00   0.00   73
  3  ω    -30.00  54.00   1.00    1.00    --   37.66 -57.00  60.00   84
  4  ω     21.00 105.00   1.00    1.00    --   37.66  57.00-180.00   84
  5  ω    -30.00  54.00   1.00    1.00    --   37.66 -57.00 -60.00   84
  6  ω     21.00 105.00   1.00    1.00    --   37.66  57.00-120.00   84
  7  ω     39.00 109.00   1.00    1.00    --  108.00 -94.00-120.00   70
  8  ω     38.00 129.00   1.00    1.00    --  108.00 -30.00-150.00   91
  9  ω     81.00 176.00   1.00    1.00    --  108.00  77.00 -30.00   95
 10  ω     38.00 116.00   1.00    1.00    --  108.00-111.00-150.00   78
 11  ω     39.00 109.00   1.00    1.00    --  108.00 -94.00 -60.00   70
 12  ω     38.00 129.00   1.00    1.00    --  108.00 -30.00 120.00   91
 13  ω    100.00 178.00   1.00    1.00    --  108.00 111.00   0.00   78
 14  ω     41.00 126.00   1.00    1.00    --  108.00 -61.00 -60.00   85
 15  ω    -30.00  54.00   1.00    1.00    --   37.66 -57.00 120.00   84
 16  ω     21.00 105.00   1.00    1.00    --   37.66  57.00 -60.00   84
 17  ω     11.00 105.00   1.00    1.00    --   37.66  77.00   0.00   94
 18  ω    -30.00  54.00   1.00    1.00    --   37.66 -57.00   0.00   84
 19  ω    -30.00  54.00   1.00    1.00    --   37.66 -57.00-180.00   84
 20  ω     21.00 105.00   1.00    1.00    --   37.66  57.00  90.00   84
 21  ω     70.00 178.00   1.00    1.00    --  108.00  15.00 -90.00  108
 22  ω     70.00 178.00   1.00    1.00    --  108.00  15.00  90.00  108
 23  ω     70.00 178.00   1.00    1.00    --  108.00  15.00-180.00  108
 24  ω     91.00 120.00   1.00    1.00    --  108.00  45.00 -60.00   29
 25  ω     41.00 126.00   1.00    1.00    --  108.00 -61.00  30.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0106024000
_diffrn_orient_matrix_UB_12      0.0045302000
_diffrn_orient_matrix_UB_13      0.1101425000
_diffrn_orient_matrix_UB_21      0.0217999000
_diffrn_orient_matrix_UB_22      -0.0877940000
_diffrn_orient_matrix_UB_23      0.0066640000
_diffrn_orient_matrix_UB_31      0.2406184000
_diffrn_orient_matrix_UB_32      0.0081487000
_diffrn_orient_matrix_UB_33      0.0098983000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2650
_reflns_number_total             3000
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.989
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0734
_refine_ls_restrained_S_all      1.086
_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)+(0.1209P)²+0.9222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1976
_refine_ls_wR_factor_ref         0.2052
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17), C18(H18),
 C20(H20)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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
O1 O -0.0084(2) 0.38407(9) 0.14462(13) 0.0428(4) Uani 1 1 d . . . . .
F2 F -0.1568(2) 0.49944(9) 0.09421(12) 0.0544(5) Uani 1 1 d . . . . .
F3 F -0.0977(2) 0.47628(8) 0.25260(11) 0.0528(4) Uani 1 1 d . . . . .
N4 N 0.2003(3) 0.50422(9) 0.15834(12) 0.0308(4) Uani 1 1 d . . . . .
C5 C 0.3261(3) 0.39458(12) 0.07753(15) 0.0308(5) Uani 1 1 d . . . . .
C6 C 0.3514(3) 0.46850(12) 0.11628(15) 0.0313(5) Uani 1 1 d . . . . .
H6 H 0.480014 0.492997 0.111939 0.038 Uiso 1 1 calc R . . . .
C7 C 0.2376(3) 0.57950(12) 0.19773(15) 0.0328(5) Uani 1 1 d . . . . .
C8 C 0.4472(3) 0.28948(13) -0.01817(17) 0.0391(5) Uani 1 1 d . . . . .
H8 H 0.550893 0.267819 -0.054146 0.047 Uiso 1 1 calc R . . . .
C9 C 0.1387(3) 0.35401(12) 0.09079(15) 0.0319(5) Uani 1 1 d . . . . .
C10 C 0.1057(3) 0.28236(12) 0.05081(16) 0.0359(5) Uani 1 1 d . . . . .
H10 H -0.016858 0.255778 0.062309 0.043 Uiso 1 1 calc R . . . .
C11 C 0.4802(3) 0.35931(12) 0.02327(16) 0.0348(5) Uani 1 1 d . . . . .
H11 H 0.606966 0.384339 0.015672 0.042 Uiso 1 1 calc R . . . .
C12 C 0.2557(4) 0.24906(13) -0.00717(16) 0.0375(5) Uani 1 1 d . . . . .
C13 C 0.4242(4) 0.59619(14) 0.24827(18) 0.0432(6) Uani 1 1 d . . . . .
H13 H 0.527542 0.558879 0.256933 0.052 Uiso 1 1 calc R . . . .
C14 C 0.0836(4) 0.63556(13) 0.18490(17) 0.0412(5) Uani 1 1 d . . . . .
H14 H -0.041573 0.624644 0.150493 0.049 Uiso 1 1 calc R . . . .
N15 N 0.2164(4) 0.18101(12) -0.05240(18) 0.0538(6) Uani 1 1 d . . . . .
B16 B -0.0235(4) 0.46542(14) 0.16313(18) 0.0337(5) Uani 1 1 d . . . . .
C17 C 0.1184(4) 0.70767(14) 0.22379(19) 0.0487(6) Uani 1 1 d . . . . .
H17 H 0.015561 0.745207 0.215519 0.058 Uiso 1 1 calc R . . . .
C18 C 0.4558(4) 0.66942(16) 0.2860(2) 0.0537(7) Uani 1 1 d . . . . .
H18 H 0.581715 0.681085 0.319430 0.064 Uiso 1 1 calc R . . . .
C19 C 0.0255(4) 0.13730(16) -0.0361(2) 0.0511(7) Uani 1 1 d . . . . .
C20 C 0.3032(5) 0.72457(14) 0.2746(2) 0.0524(7) Uani 1 1 d . . . . .
H20 H 0.324569 0.773089 0.300931 0.063 Uiso 1 1 calc R . . . .
C21 C 0.0301(6) 0.09446(18) 0.0579(2) 0.0626(8) Uani 1 1 d . . . . .
C22 C 0.3493(6) 0.1506(2) -0.1284(3) 0.0771(10) Uani 1 1 d . . . . .
H22A H 0.260169 0.133806 -0.182880 0.092 Uiso 1 1 calc R . . . .
H22B H 0.439429 0.191161 -0.150290 0.092 Uiso 1 1 calc R . . . .
C23 C 0.4769(7) 0.0873(3) -0.0935(5) 0.125(2) Uani 1 1 d . . . . .
H23A H 0.565790 0.070642 -0.143033 0.188 Uiso 1 1 calc GR . . . .
H23B H 0.387884 0.045789 -0.075859 0.188 Uiso 1 1 calc GR . . . .
H23C H 0.561924 0.103384 -0.038289 0.188 Uiso 1 1 calc GR . . . .
H19A H -0.091(5) 0.1731(18) -0.044(2) 0.048(7) Uiso 1 1 d . . . . .
H19B H 0.001(5) 0.1053(19) -0.089(2) 0.059(8) Uiso 1 1 d . . . . .
H21A H 0.154(6) 0.056(2) 0.061(3) 0.087(12) Uiso 1 1 d . . . . .
H21B H 0.041(6) 0.128(2) 0.117(3) 0.074(10) Uiso 1 1 d . . . . .
H21C H -0.097(6) 0.068(2) 0.064(3) 0.078(11) 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
O1 C9 1.337(3) . ?
O1 B16 1.447(3) . ?
F2 B16 1.384(3) . ?
F3 B16 1.368(3) . ?
N4 C6 1.310(3) . ?
N4 C7 1.438(3) . ?
N4 B16 1.585(3) . ?
C5 C6 1.404(3) . ?
C5 C9 1.410(3) . ?
C5 C11 1.411(3) . ?
C7 C13 1.383(3) . ?
C7 C14 1.391(3) . ?
C8 C11 1.360(3) . ?
C8 C12 1.426(3) . ?
C9 C10 1.380(3) . ?
C10 C12 1.408(3) . ?
C12 N15 1.361(3) . ?
C13 C18 1.392(4) . ?
C14 C17 1.383(3) . ?
N15 C19 1.465(3) . ?
N15 C22 1.487(4) . ?
C17 C20 1.376(4) . ?
C18 C20 1.373(4) . ?
C19 C21 1.506(5) . ?
C22 C23 1.442(7) . ?

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
C9 O1 B16 122.64(16) . . ?
C6 N4 C7 119.59(17) . . ?
C6 N4 B16 120.00(17) . . ?
C7 N4 B16 120.38(16) . . ?
C6 C5 C9 119.50(18) . . ?
C6 C5 C11 122.48(18) . . ?
C9 C5 C11 118.00(19) . . ?
N4 C6 C5 122.42(18) . . ?
C13 C7 N4 120.51(19) . . ?
C13 C7 C14 120.1(2) . . ?
C14 C7 N4 119.40(19) . . ?
C11 C8 C12 120.8(2) . . ?
O1 C9 C5 120.02(19) . . ?
O1 C9 C10 118.98(18) . . ?
C10 C9 C5 120.99(19) . . ?
C9 C10 C12 120.73(19) . . ?
C8 C11 C5 121.40(19) . . ?
C10 C12 C8 117.9(2) . . ?
N15 C12 C8 121.4(2) . . ?
N15 C12 C10 120.7(2) . . ?
C7 C13 C18 119.3(2) . . ?
C17 C14 C7 119.4(2) . . ?
C12 N15 C19 121.2(2) . . ?
C12 N15 C22 122.8(2) . . ?
C19 N15 C22 115.7(2) . . ?
O1 B16 N4 110.10(16) . . ?
F2 B16 O1 109.95(19) . . ?
F2 B16 N4 108.13(17) . . ?
F3 B16 O1 109.10(19) . . ?
F3 B16 F2 110.08(19) . . ?
F3 B16 N4 109.47(18) . . ?
C20 C17 C14 120.8(2) . . ?
C20 C18 C13 120.7(2) . . ?
N15 C19 C21 114.4(3) . . ?
C18 C20 C17 119.6(2) . . ?
C23 C22 N15 111.4(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.407
_oxdiff_exptl_absorpt_empirical_full_min 0.695
####################################################################### 
# 
# 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_exp_15944
_database_code_depnum_ccdc_archive 'CCDC 1915932'
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;
_audit_creation_date             2019-02-27
_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         '2(C27 H24 B F2 N3 O), 2(C H2 Cl2)'
_chemical_formula_sum            'C56 H52 B2 Cl4 F4 N6 O2'
_chemical_formula_weight         1080.45
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3782(3)
_cell_length_b                   11.9598(5)
_cell_length_c                   18.7878(8)
_cell_angle_alpha                93.233(3)
_cell_angle_beta                 95.900(4)
_cell_angle_gamma                105.309(4)
_cell_volume                     1369.77(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8064
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.4810
_cell_measurement_theta_min      3.8310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.464
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25282
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.941
_diffrn_reflns_theta_min         3.847
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     11.00 105.00   1.00    1.00    --   37.66  77.00 150.00   94
  2  ω    -32.00  57.00   1.00    1.00    --   37.66 -37.00   0.00   89
  3  ω     -4.00  77.00   1.00    1.00    --   37.66 -99.00  30.00   81
  4  ω    -32.00  57.00   1.00    1.00    --   37.66 -37.00 -90.00   89
  5  ω    -30.00  54.00   1.00    1.00    --   37.66 -57.00  60.00   84
  6  ω     21.00 105.00   1.00    1.00    --   37.66  57.00 -90.00   84
  7  ω     -4.00  77.00   1.00    1.00    --   37.66 -99.00 -30.00   81
  8  ω    -30.00  64.00   1.00    1.00    --   37.66 -77.00-180.00   94
  9  ω     39.00 109.00   1.00    1.78    --  108.00 -94.00-180.00   70
 10  ω     39.00 109.00   1.00    1.78    --  108.00 -94.00  90.00   70
 11  ω     91.00 176.00   1.00    1.78    --  108.00  45.00-120.00   85
 12  ω     39.00 109.00   1.00    1.78    --  108.00 -94.00   0.00   70
 13  ω     40.00 125.00   1.00    1.78    --  108.00 -45.00 -30.00   85
 14  ω     40.00 125.00   1.00    1.78    --  108.00 -45.00  60.00   85
 15  ω    100.00 178.00   1.00    1.78    --  108.00 111.00 -90.00   78
 16  ω     90.00 175.00   1.00    1.78    --  108.00  61.00  60.00   85
 17  ω     40.00 125.00   1.00    1.78    --  108.00 -45.00-120.00   85
 18  ω     38.00 116.00   1.00    1.78    --  108.00-111.00-180.00   78
 19  ω     40.00 125.00   1.00    1.78    --  108.00 -45.00 150.00   85
 20  ω     39.00 177.00   1.00    1.78    --  108.00   0.00  30.00  138
 21  ω     39.00 109.00   1.00    1.78    --  108.00 -94.00 -90.00   70
 22  ω     11.00 105.00   1.00    1.00    --   37.66  77.00  60.00   94
 23  ω     11.00 105.00   1.00    1.00    --   37.66  77.00  30.00   94
 24  ω     21.00 105.00   1.00    1.00    --   37.66  57.00-120.00   84
 25  ω     11.00 105.00   1.00    1.00    --   37.66  77.00 -60.00   94
 26  ω     18.00  91.00   1.00    1.00    --   37.66-125.00 -90.00   73
 27  ω     21.00 105.00   1.00    1.00    --   37.66  57.00 -30.00   84
 28  ω     70.00 178.00   1.00    1.78    --  108.00  15.00-180.00  108
 29  ω     81.00 176.00   1.00    1.78    --  108.00  77.00-120.00   95
 30  ω     81.00 176.00   1.00    1.78    --  108.00  77.00 -60.00   95
 31  ω     81.00 176.00   1.00    1.78    --  108.00  77.00   0.00   95
 32  ω     87.00 178.00   1.00    1.78    --  108.00  30.00-150.00   91
 33  ω     81.00 176.00   1.00    1.78    --  108.00  77.00 -90.00   95
 34  ω     81.00 176.00   1.00    1.78    --  108.00  77.00 150.00   95
 35  ω     81.00 176.00   1.00    1.78    --  108.00  77.00 -30.00   95
 36  ω     91.00 176.00   1.00    1.78    --  108.00  45.00-150.00   85
 37  ω     81.00 176.00   1.00    1.78    --  108.00  77.00  30.00   95
 38  ω     81.00 176.00   1.00    1.78    --  108.00  77.00  60.00   95
 39  ω     90.00 175.00   1.00    1.78    --  108.00  61.00  90.00   85
 40  ω     18.00 107.00   1.00    1.00    --   37.66  37.00  30.00   89
 41  ω     18.00 107.00   1.00    1.00    --   37.66  37.00-120.00   89
 42  ω     11.00 105.00   1.00    1.00    --   37.66  77.00 -90.00   94
 43  ω     18.00  91.00   1.00    1.00    --   37.66-125.00-180.00   73
 44  ω     11.00  82.00   1.00    1.00    --   37.66  77.00   0.00   71
 45  ω     21.00 105.00   1.00    1.00    --   37.66  57.00 150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0207727000
_diffrn_orient_matrix_UB_12      -0.0748881000
_diffrn_orient_matrix_UB_13      0.0643393000
_diffrn_orient_matrix_UB_21      -0.0847187000
_diffrn_orient_matrix_UB_22      -0.1109419000
_diffrn_orient_matrix_UB_23      -0.0519909000
_diffrn_orient_matrix_UB_31      0.2367562000
_diffrn_orient_matrix_UB_32      -0.0074537000
_diffrn_orient_matrix_UB_33      -0.0021821000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4164
_reflns_number_total             5311
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.324
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0715
_refine_ls_restrained_S_all      1.071
_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)+(0.1167P)²+0.3417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1950
_refine_ls_wR_factor_ref         0.2128
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C10(H10), C5(H5), C13(H13), C11(H11), C3(H3), C7(H7), C4(H4),
 C22(H22), C21(H21), C18(H18), C24(H24), C15(H15), C16(H16), C25(H25), C23(H23),
  C17(H17), C14(H14)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_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 0.0891(3) 0.32080(12) 0.13910(9) 0.0758(4) Uani 1 1 d . . . . .
N2 N -0.1641(3) 0.41847(14) 0.08368(9) 0.0479(4) Uani 1 1 d . . . . .
C26 C -0.2576(3) 0.49982(17) 0.09836(10) 0.0471(4) Uani 1 1 d . . . . .
H26 H -0.391391 0.497302 0.072512 0.057 Uiso 1 1 calc R . . . .
F2 F 0.2186(2) 0.46456(14) 0.06982(8) 0.0739(4) Uani 1 1 d . . . . .
O1 O 0.1304(3) 0.50925(16) 0.18276(10) 0.0716(5) Uani 1 1 d . . . . .
C10 C -0.2648(4) 0.68023(18) 0.16722(11) 0.0553(5) Uani 1 1 d . . . . .
H10 H -0.389754 0.683056 0.137971 0.066 Uiso 1 1 calc R . . . .
C6 C -0.2817(3) 0.31980(17) 0.03510(10) 0.0484(5) Uani 1 1 d . . . . .
C9 C -0.1633(3) 0.59214(17) 0.15222(10) 0.0483(4) Uani 1 1 d . . . . .
C5 C -0.4976(4) 0.26516(18) 0.04088(11) 0.0532(5) Uani 1 1 d . . . . .
H5 H -0.566987 0.292287 0.076643 0.064 Uiso 1 1 calc R . . . .
C13 C 0.1094(4) 0.6726(2) 0.25368(13) 0.0642(6) Uani 1 1 d . . . . .
H13 H 0.235666 0.670810 0.282613 0.077 Uiso 1 1 calc R . . . .
C11 C -0.1829(4) 0.76171(19) 0.22400(12) 0.0609(6) Uani 1 1 d . . . . .
H11 H -0.250446 0.820298 0.232810 0.073 Uiso 1 1 calc R . . . .
C28 C -0.5143(4) 0.12739(18) -0.06050(11) 0.0541(5) Uani 1 1 d . . . . .
N3 N 0.0791(4) 0.83368(18) 0.33079(11) 0.0718(6) Uani 1 1 d . . . . .
C3 C -0.2941(4) 0.1849(2) -0.06540(12) 0.0578(5) Uani 1 1 d . . . . .
H3 H -0.223949 0.159141 -0.101417 0.069 Uiso 1 1 calc R . . . .
C8 C 0.0289(4) 0.59128(19) 0.19569(12) 0.0547(5) Uani 1 1 d . . . . .
C12 C 0.0045(4) 0.75689(19) 0.26934(12) 0.0594(6) Uani 1 1 d . . . . .
N1 N -0.6300(4) 0.03415(18) -0.10705(12) 0.0717(6) Uani 1 1 d . . . . .
C7 C -0.1806(4) 0.27800(19) -0.01842(11) 0.0542(5) Uani 1 1 d . . . . .
H7 H -0.034344 0.313506 -0.022431 0.065 Uiso 1 1 calc R . . . .
C4 C -0.6115(4) 0.17083(19) -0.00575(12) 0.0576(5) Uani 1 1 d . . . . .
H4 H -0.756844 0.135055 -0.000713 0.069 Uiso 1 1 calc R . . . .
C20 C 0.0457(4) 0.94647(19) 0.33590(12) 0.0602(6) Uani 1 1 d . . . . .
B1 B 0.0750(4) 0.4275(2) 0.11977(14) 0.0559(6) Uani 1 1 d . . . . .
C19 C 0.1896(5) 0.7985(2) 0.39259(13) 0.0703(7) Uani 1 1 d . . . . .
C1 C -0.5254(6) -0.0127(3) -0.16114(18) 0.0929(10) Uani 1 1 d . . . . .
H1A H -0.462488 0.047527 -0.190470 0.139 Uiso 1 1 calc GR . . . .
H1B H -0.631711 -0.074333 -0.190582 0.139 Uiso 1 1 calc GR . . . .
H1C H -0.412184 -0.042700 -0.138512 0.139 Uiso 1 1 calc GR . . . .
C22 C -0.0340(6) 0.9833(3) 0.39552(15) 0.0825(8) Uani 1 1 d . . . . .
H22 H -0.070269 0.933305 0.431202 0.099 Uiso 1 1 calc R . . . .
C2 C -0.8462(5) -0.0301(2) -0.09530(16) 0.0811(8) Uani 1 1 d . . . . .
H2A H -0.844261 -0.051062 -0.046710 0.122 Uiso 1 1 calc GR . . . .
H2B H -0.893610 -0.099324 -0.127764 0.122 Uiso 1 1 calc GR . . . .
H2C H -0.945393 0.017131 -0.103589 0.122 Uiso 1 1 calc GR . . . .
C21 C 0.0937(6) 1.0204(2) 0.28317(16) 0.0861(8) Uani 1 1 d . . . . .
H21 H 0.146350 0.996739 0.242185 0.103 Uiso 1 1 calc R . . . .
C18 C 0.3898(6) 0.8656(3) 0.42269(17) 0.0919(9) Uani 1 1 d . . . . .
H18 H 0.456806 0.932776 0.402173 0.110 Uiso 1 1 calc R . . . .
C24 C -0.0121(7) 1.1660(3) 0.3514(2) 0.1031(12) Uani 1 1 d . . . . .
H24 H -0.030354 1.240473 0.356975 0.124 Uiso 1 1 calc R . . . .
C15 C 0.2057(9) 0.6703(3) 0.4842(2) 0.1200(15) Uani 1 1 d . . . . .
H15 H 0.141578 0.603105 0.505181 0.144 Uiso 1 1 calc R . . . .
C16 C 0.4034(8) 0.7373(4) 0.51273(19) 0.1097(13) Uani 1 1 d . . . . .
H16 H 0.476711 0.715840 0.552833 0.132 Uiso 1 1 calc R . . . .
C25 C -0.0602(7) 1.0930(3) 0.40277(19) 0.1059(12) Uani 1 1 d . . . . .
H25 H -0.112053 1.117291 0.443765 0.127 Uiso 1 1 calc R . . . .
C23 C 0.0633(7) 1.1309(3) 0.2912(2) 0.1060(12) Uani 1 1 d . . . . .
H23 H 0.094635 1.181145 0.255378 0.127 Uiso 1 1 calc R . . . .
C17 C 0.4943(7) 0.8344(4) 0.4836(2) 0.1127(12) Uani 1 1 d . . . . .
H17 H 0.629455 0.881908 0.504301 0.135 Uiso 1 1 calc R . . . .
C14 C 0.0942(7) 0.7004(3) 0.42295(18) 0.1048(12) Uani 1 1 d . . . . .
H14 H -0.043109 0.653689 0.403474 0.126 Uiso 1 1 calc R . . . .
Cl2 Cl 0.6639(3) 0.35983(18) 0.28294(11) 0.1910(8) Uani 1 1 d . . . . .
Cl1 Cl 0.4643(3) 0.49910(16) 0.36831(9) 0.1733(7) Uani 1 1 d . . . . .
C27 C 0.5022(9) 0.4488(5) 0.2862(3) 0.1377(17) Uani 1 1 d . . . . .
H27A H 0.359792 0.408235 0.260762 0.165 Uiso 1 1 calc R . . . .
H27B H 0.562429 0.515239 0.260141 0.165 Uiso 1 1 calc R . . . .


_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 B1 1.369(3) . ?
N2 C26 1.299(3) . ?
N2 C6 1.435(2) . ?
N2 B1 1.578(3) . ?
C26 C9 1.415(3) . ?
F2 B1 1.388(3) . ?
O1 C8 1.335(3) . ?
O1 B1 1.443(3) . ?
C10 C9 1.404(3) . ?
C10 C11 1.364(3) . ?
C6 C5 1.378(3) . ?
C6 C7 1.387(3) . ?
C9 C8 1.404(3) . ?
C5 C4 1.376(3) . ?
C13 C8 1.378(3) . ?
C13 C12 1.383(3) . ?
C11 C12 1.411(3) . ?
C28 C3 1.406(3) . ?
C28 N1 1.370(3) . ?
C28 C4 1.397(3) . ?
N3 C12 1.393(3) . ?
N3 C20 1.420(3) . ?
N3 C19 1.437(3) . ?
C3 C7 1.369(3) . ?
N1 C1 1.437(4) . ?
N1 C2 1.437(4) . ?
C20 C22 1.373(4) . ?
C20 C21 1.370(4) . ?
C19 C18 1.361(4) . ?
C19 C14 1.358(4) . ?
C22 C25 1.366(4) . ?
C21 C23 1.387(5) . ?
C18 C17 1.383(5) . ?
C24 C25 1.342(6) . ?
C24 C23 1.361(5) . ?
C15 C16 1.341(6) . ?
C15 C14 1.404(5) . ?
C16 C17 1.329(6) . ?
Cl2 C27 1.668(5) . ?
Cl1 C27 1.688(5) . ?

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 N2 C6 119.31(17) . . ?
C26 N2 B1 120.25(17) . . ?
C6 N2 B1 120.44(16) . . ?
N2 C26 C9 122.47(18) . . ?
C8 O1 B1 124.27(18) . . ?
C11 C10 C9 121.0(2) . . ?
C5 C6 N2 120.35(18) . . ?
C5 C6 C7 118.93(19) . . ?
C7 C6 N2 120.71(18) . . ?
C10 C9 C26 122.00(19) . . ?
C8 C9 C26 119.15(18) . . ?
C8 C9 C10 118.67(18) . . ?
C4 C5 C6 120.62(19) . . ?
C8 C13 C12 120.7(2) . . ?
C10 C11 C12 119.8(2) . . ?
N1 C28 C3 122.3(2) . . ?
N1 C28 C4 121.2(2) . . ?
C4 C28 C3 116.58(19) . . ?
C12 N3 C20 122.35(19) . . ?
C12 N3 C19 119.93(19) . . ?
C20 N3 C19 117.70(18) . . ?
C7 C3 C28 121.6(2) . . ?
O1 C8 C9 120.32(18) . . ?
O1 C8 C13 119.5(2) . . ?
C13 C8 C9 120.1(2) . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 N3 120.1(2) . . ?
N3 C12 C11 120.4(2) . . ?
C28 N1 C1 120.6(2) . . ?
C28 N1 C2 120.4(2) . . ?
C2 N1 C1 118.3(2) . . ?
C3 C7 C6 120.6(2) . . ?
C5 C4 C28 121.7(2) . . ?
C22 C20 N3 119.4(2) . . ?
C21 C20 N3 121.6(2) . . ?
C21 C20 C22 118.9(2) . . ?
F1 B1 N2 110.06(19) . . ?
F1 B1 F2 109.32(19) . . ?
F1 B1 O1 109.2(2) . . ?
F2 B1 N2 107.98(19) . . ?
F2 B1 O1 110.0(2) . . ?
O1 B1 N2 110.25(18) . . ?
C18 C19 N3 120.0(3) . . ?
C14 C19 N3 120.8(3) . . ?
C14 C19 C18 119.1(3) . . ?
C25 C22 C20 120.5(3) . . ?
C20 C21 C23 119.6(3) . . ?
C19 C18 C17 120.5(4) . . ?
C25 C24 C23 119.9(3) . . ?
C16 C15 C14 120.9(4) . . ?
C17 C16 C15 119.8(3) . . ?
C24 C25 C22 120.8(3) . . ?
C24 C23 C21 120.2(3) . . ?
C16 C17 C18 120.6(4) . . ?
C19 C14 C15 119.0(4) . . ?
Cl2 C27 Cl1 117.2(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.811
_oxdiff_exptl_absorpt_empirical_full_min 0.587
