# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_bhasod
_database_code_depnum_ccdc_archive 'CCDC 1920190'
loop_
_audit_author_name
_audit_author_address
'Neil Champness'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2019-06-02 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;
_nottingham_internal_coll_name   BHASOD
_nottingham_internal_coll_number 17813
_nottingham_internal_coll_client HMH/DLK
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '30.00, 120.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pcxhh4
_nottingham_internal_coll_date   09/08/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 13/08/2018
_nottingham_internal_process_user pcxhh4
_nottingham_internal_solution_date 19/8/2018
_nottingham_internal_solution_user pcxhh4
_nottingham_internal_refinement_date 19/8/2018
_nottingham_internal_refinement_user pcxhh4
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date ?
_nottingham_internal_validation_user ?
_nottingham_internal_archive_date ?
_refine_special_details          ?
_audit_creation_date             2018-08-22
_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        BhHASOD
_chemical_formula_moiety         'C29 H25 B F2 N4'
_chemical_formula_sum            'C29 H25 B F2 N4'
_chemical_formula_weight         478.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H22 B1 F2 N3'
_chemical_oxdiff_usercomment     
'BHASOD #17813 GVB-1559 IN FOBLIN IN MICROMOUNT FOR  HMH/NRC'
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'

_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        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
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                   13.5686(4)
_cell_length_b                   13.2178(5)
_cell_length_c                   13.7790(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.947(4)
_cell_angle_gamma                90
_cell_volume                     2376.12(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2253
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0910
_cell_measurement_theta_min      4.7210
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (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            'metallic orangish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -9 0.0559
0 1 9 0.0089
-8 0 -1 0.0960
0 6 6 0.0165
0 -6 -6 0.0165
-7 2 7 0.0382
9 0 0 0.0752
1 6 -7 0.0721
-1 -7 5 0.0010

_exptl_crystal_preparation       'in fobolin on micromount for HMH/NRC'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.033
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
0.0002 -0.9971 -8.9954 0.4105 -0.9672 -0.0576
-0.0002 0.9971 8.9954 -0.4105 0.9672 0.0576
-7.9987 -0.0092 -0.9993 0.2090 -0.3708 0.8866
-0.0010 5.9941 6.0028 -0.8645 0.4654 0.1026
0.0010 -5.9941 -6.0028 0.8645 -0.4654 -0.1026
-6.9992 1.9886 6.9978 -0.3010 0.4840 0.8397
8.9986 0.0106 -0.0001 -0.1976 0.2920 -1.0031
0.9990 5.9984 -6.9891 -0.4536 -0.9479 -0.0746
-0.9988 -6.9972 4.9892 0.6310 0.7591 0.0525

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4769
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.695
_diffrn_reflns_theta_min         4.726
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -111.00 -23.00   1.00   30.00    --  -42.83 -57.00 -60.00   88
  2  ω     52.00  79.00   1.00   30.00    --   42.83 -99.00-180.00   27
  3  ω    -27.00  68.00   1.00   30.00    --   42.83 -57.00 120.00   95
  4  ω     32.00  89.00   1.00  120.00    --  107.00 -30.00 120.00   57
  5  ω     37.00  78.00   1.00  120.00    --  107.00 -30.00-150.00   41
  6  ω     40.00  68.00   1.00  120.00    --  107.00 -45.00   0.00   28
  7  ω     88.00 134.00   1.00  120.00    --  107.00  45.00-120.00   46
  8  ω     45.00 118.00   1.00  120.00    --  107.00-125.00  60.00   73
  9  ω    151.00 178.00   1.00  120.00    --  107.00  45.00-120.00   27
 10  ω     38.00  87.00   1.00  120.00    --  107.00 -30.00  60.00   49
 11  ω     56.00  92.00   1.00  120.00    --  107.00-125.00 120.00   36
 12  ω     35.00 123.00   1.00  120.00    --  107.00 -77.00-120.00   88
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0218294000
_diffrn_orient_matrix_UB_12      -0.1108339000
_diffrn_orient_matrix_UB_13      -0.0333450000
_diffrn_orient_matrix_UB_21      0.0324915000
_diffrn_orient_matrix_UB_22      -0.0337834000
_diffrn_orient_matrix_UB_23      0.1112693000
_diffrn_orient_matrix_UB_31      -0.1114890000
_diffrn_orient_matrix_UB_32      0.0120265000
_diffrn_orient_matrix_UB_33      0.0050660000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2000
_reflns_number_total             2358
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.040
_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)+(0.0500P)²+2.0829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1102
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C3(H3), C1(H1), C2(H2), C11(H11), C13(H13)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.82042(7) 0.71829(7) 0.56746(7) 0.0327(2) Uani 1 1 d . . . . .
N3 N 0.69388(10) 0.58767(9) 0.55782(9) 0.0243(3) Uani 1 1 d . . . . .
N4 N 0.41575(13) 0.52693(12) 0.86723(12) 0.0413(4) Uani 1 1 d . . . . .
C1 C 0.750000 0.10734(17) 0.500000 0.0338(5) Uani 1 2 d S T P . .
H1 H 0.750000 0.035469 0.500000 0.041 Uiso 1 2 calc RS T P . .
C2 C 0.66932(14) 0.16011(12) 0.43528(13) 0.0342(4) Uani 1 1 d . . . . .
H2 H 0.613943 0.124374 0.391498 0.041 Uiso 1 1 calc R . . . .
C3 C 0.67030(13) 0.26479(12) 0.43512(12) 0.0319(4) Uani 1 1 d . . . . .
H3 H 0.615973 0.300844 0.390223 0.038 Uiso 1 1 calc R . . . .
C4 C 0.750000 0.31743(15) 0.500000 0.0245(4) Uani 1 2 d S T P . .
C5 C 0.750000 0.42999(15) 0.500000 0.0238(4) Uani 1 2 d S T P . .
C6 C 0.69381(11) 0.48172(11) 0.55552(11) 0.0245(3) Uani 1 1 d . . . . .
C7 C 0.63414(12) 0.44641(11) 0.61912(11) 0.0252(3) Uani 1 1 d . . . . .
C8 C 0.59983(11) 0.53239(11) 0.65891(11) 0.0251(3) Uani 1 1 d . . . . .
C9 C 0.53602(12) 0.53330(11) 0.73014(11) 0.0254(3) Uani 1 1 d . . . . .
C10 C 0.44497(12) 0.47845(12) 0.70988(12) 0.0296(3) Uani 1 1 d . . . . .
H10 H 0.421814 0.441459 0.648722 0.036 Uiso 1 1 calc R . . . .
C11 C 0.38856(13) 0.47833(13) 0.77966(13) 0.0355(4) Uani 1 1 d . . . . .
H11 H 0.326322 0.441035 0.763834 0.043 Uiso 1 1 calc R . . . .
C13 C 0.50308(16) 0.57948(13) 0.88633(13) 0.0401(4) Uani 1 1 d . . . . .
H13 H 0.524517 0.614714 0.948690 0.048 Uiso 1 1 calc R . . . .
C14 C 0.56459(14) 0.58591(12) 0.82086(12) 0.0321(4) Uani 1 1 d . . . . .
H14 H 0.625241 0.625682 0.837872 0.039 Uiso 1 1 calc R . . . .
C15 C 0.63809(12) 0.61787(11) 0.61987(11) 0.0253(3) Uani 1 1 d . . . . .
C16 C 0.61429(14) 0.33915(12) 0.64408(13) 0.0330(4) Uani 1 1 d . . . . .
H16A H 0.566300 0.307629 0.585496 0.049 Uiso 1 1 calc GR . . . .
H16B H 0.584704 0.338406 0.701444 0.049 Uiso 1 1 calc GR . . . .
H16C H 0.678918 0.301352 0.661603 0.049 Uiso 1 1 calc GR . . . .
C17 C 0.62129(13) 0.72723(11) 0.63817(13) 0.0318(4) Uani 1 1 d . . . . .
H17A H 0.687569 0.761928 0.659574 0.048 Uiso 1 1 calc GR . . . .
H17B H 0.585984 0.733322 0.691122 0.048 Uiso 1 1 calc GR . . . .
H17C H 0.579305 0.758093 0.575805 0.048 Uiso 1 1 calc GR . . . .
B1 B 0.750000 0.65741(17) 0.500000 0.0255(5) Uani 1 2 d S T P . .


_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 1.3916(16) . ?
N3 C6 1.4007(19) . ?
N3 C15 1.349(2) . ?
N3 B1 1.5484(18) . ?
N4 C11 1.327(2) . ?
N4 C13 1.336(3) . ?
C1 C2 1.394(2) 2_656 ?
C1 C2 1.394(2) . ?
C3 C2 1.384(2) . ?
C4 C3 1.3862(19) . ?
C4 C3 1.3861(19) 2_656 ?
C4 C5 1.488(3) . ?
C6 C5 1.3981(18) . ?
C6 C7 1.425(2) . ?
C7 C16 1.501(2) . ?
C8 C7 1.396(2) . ?
C8 C9 1.476(2) . ?
C8 C15 1.410(2) . ?
C9 C10 1.393(2) . ?
C9 C14 1.389(2) . ?
C10 C11 1.384(2) . ?
C14 C13 1.390(3) . ?
C15 C17 1.496(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
C6 N3 B1 125.51(13) . . ?
C15 N3 C6 108.25(12) . . ?
C15 N3 B1 126.23(13) . . ?
C11 N4 C13 116.17(15) . . ?
C2 C1 C2 120.0(2) . 2_656 ?
C3 C2 C1 119.67(16) . . ?
C2 C3 C4 120.46(16) . . ?
C3 C4 C3 119.8(2) 2_656 . ?
C3 C4 C5 120.12(10) . . ?
C3 C4 C5 120.12(10) 2_656 . ?
C6 C5 C4 119.28(9) 2_656 . ?
C6 C5 C4 119.28(9) . . ?
C6 C5 C6 121.43(19) 2_656 . ?
N3 C6 C7 108.09(12) . . ?
C5 C6 N3 120.28(14) . . ?
C5 C6 C7 131.58(14) . . ?
C6 C7 C16 128.19(14) . . ?
C8 C7 C6 106.38(13) . . ?
C8 C7 C16 125.37(14) . . ?
C7 C8 C9 125.97(14) . . ?
C7 C8 C15 107.75(14) . . ?
C15 C8 C9 126.27(13) . . ?
C10 C9 C8 120.83(14) . . ?
C14 C9 C8 122.17(14) . . ?
C14 C9 C10 116.98(15) . . ?
C11 C10 C9 119.40(15) . . ?
N4 C11 C10 124.24(17) . . ?
N4 C13 C14 124.22(16) . . ?
C9 C14 C13 118.98(16) . . ?
N3 C15 C8 109.53(13) . . ?
N3 C15 C17 122.08(14) . . ?
C8 C15 C17 128.38(14) . . ?
F1 B1 F1 109.34(17) . 2_656 ?
F1 B1 N3 110.19(6) 2_656 2_656 ?
F1 B1 N3 110.09(6) 2_656 . ?
F1 B1 N3 110.19(6) . . ?
F1 B1 N3 110.09(6) . 2_656 ?
N3 B1 N3 106.93(16) . 2_656 ?

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id BHASOD
_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 1.506
_oxdiff_exptl_absorpt_empirical_full_min 0.730
####################################################################### 
# 
# 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_cuhmhb
_database_code_depnum_ccdc_archive 'CCDC 1920193'
loop_
_audit_author_name
_audit_author_address
'Neil Champness'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2019-06-02 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;
_nottingham_internal_coll_name   CUHMHB
_nottingham_internal_coll_number 17671
_nottingham_internal_coll_client HMH/DLK
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '8.00, 2.00'
_nottingham_internal_coll_frame_width 0.50
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   08/05/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 08/05/2018
_nottingham_internal_process_user pcxhh4
_nottingham_internal_solution_date 08/05/2018
_nottingham_internal_solution_user pcxhh4
_nottingham_internal_refinement_date 06/03/2019
_nottingham_internal_refinement_user pcxhh4,pczwl,pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date ?
_nottingham_internal_validation_user ?
_nottingham_internal_archive_date ?
_refine_special_details          ?
_audit_creation_date             2019-03-06
_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         '0.5(C54 H46 B2 Cu4 F4 I4 N12)'
_chemical_formula_sum            'C27 H23 B Cu2 F2 I2 N6'
_chemical_formula_weight         861.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C29 H25 B Cu F2 I N4'
_chemical_oxdiff_usercomment     
'CUHMHB #17671 MM-652 in fomblin on micromount for HMH/DLK'
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'
Cu Cu -1.9646 0.5888 '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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   14.6653(4)
_cell_length_b                   9.0291(3)
_cell_length_c                   12.2807(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.859(2)
_cell_angle_gamma                90
_cell_volume                     1622.47(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5211
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.7740
_cell_measurement_theta_min      6.0920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    16.870
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (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            orange
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             828
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -8 0.0289
-1 0 8 0.0289
-2 6 0 0.0271
2 -5 -4 0.0275
-2 5 4 0.0275
4 5 1 0.0219
-4 -5 -1 0.0219
9 1 0 0.0126
-9 -1 -2 0.0109

_exptl_crystal_size_max          0.082
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.031
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
0.9039 -0.0217 -8.0029 -0.0572 0.0368 1.0011
-0.9039 0.0217 8.0029 0.0572 -0.0368 -1.0011
-1.9875 5.9968 -0.0287 -0.8357 0.6227 -0.0770
1.9416 -5.0078 -3.9766 0.6752 -0.4846 0.5640
-1.9416 5.0078 3.9766 -0.6752 0.4846 -0.5640
4.0186 4.9876 0.9444 -0.9469 -0.0375 -0.1616
-4.0186 -4.9876 -0.9444 0.9469 0.0375 0.1616
8.9959 0.9794 -0.0563 -0.5545 -0.7854 0.0318
-9.0198 -0.9843 -1.9430 0.5513 0.8184 0.2173

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9721
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.867
_diffrn_reflns_theta_min         5.758
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'PILATUS3 R 200K Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  13.00   0.50    2.00    --    0.00 -57.00  30.00   90
  2  ω    -22.00   9.00   0.50    2.00    --    0.00 -82.00 -60.00   62
  3  ω    -88.00 -36.00   0.50    2.00    --    0.00 -57.00  30.00  104
  4  ω     12.00  69.00   0.50    8.00    --  100.80 -30.00  30.00  114
  5  ω     47.00 100.00   0.50    8.00    --  100.80 -82.00  30.00  106
  6  ω     73.00 118.00   0.50    8.00    --  100.80 -82.00  60.00   90
  7  ω     62.00  99.00   0.50    8.00    --  100.80 -82.00 150.00   74
  8  ω     55.00 116.00   0.50    8.00    --  100.80 -82.00 -60.00  122
  9  ω     65.00 118.00   0.50    8.00    --  100.80 -82.00-150.00  106
 10  ω     77.00 103.00   0.50    8.00    --  100.80  30.00 -90.00   52
 11  ω    139.00 184.00   0.50    8.00    --  100.80  30.00 -90.00   90
 12  ω     87.00 180.00   0.50    8.00    --  100.80  82.00-180.00  186
 13  ω     19.00 132.00   0.50    8.00    --  100.80 -82.00 120.00  226
 14  ω     11.00  67.00   0.50    8.00    --  100.80 -30.00 120.00  112
 15  ω     21.00  56.00   0.50    8.00    --  100.80 -82.00 150.00   70
 16  ω     14.00  66.00   0.50    8.00    --  100.80 -30.00 150.00  104
 17  ω     16.00  49.00   0.50    8.00    --  100.80 -45.00-150.00   66
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'XtalLAB PRO MM007, PILATUS3 R 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0448350000
_diffrn_orient_matrix_UB_12      -0.1542061000
_diffrn_orient_matrix_UB_13      0.0025057000
_diffrn_orient_matrix_UB_21      -0.0952670000
_diffrn_orient_matrix_UB_22      0.0721876000
_diffrn_orient_matrix_UB_23      -0.0155485000
_diffrn_orient_matrix_UB_31      0.0040667000
_diffrn_orient_matrix_UB_32      -0.0120920000
_diffrn_orient_matrix_UB_33      -0.1246057000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode'
_diffrn_source_type              'MicroMax 007 HF'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2611
_reflns_number_total             3267
_reflns_odcompleteness_completeness 98.84
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.665
_refine_diff_density_min         -1.899
_refine_diff_density_rms         0.208
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3267
_refine_ls_number_restraints     511
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0612
_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)+(0.1464P)²+0.0787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1812
_refine_ls_wR_factor_ref         0.2068
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N6-B1 \\sim N2-B1
 with sigma of 0.02
 F7-B1 \\sim F8-B1
 with sigma of 0.02
 C13-C9 \\sim C9-C11
 with sigma of 0.02
 C14-C12 \\sim C12-C10
 with sigma of 0.02
 C14-C10 \\sim C11-C13
 with sigma of 0.02
 N2-C3 \\sim N6-C5
 with sigma of 0.02
 C3-C15 \\sim C5-C22
 with sigma of 0.02
 N6-C20 \\sim N2-C17
 with sigma of 0.02
 C17-C16 \\sim C21-C20
 with sigma of 0.02
 C22-C21 \\sim C16-C15
 with sigma of 0.02
 C18-C15 \\sim C19-C17
 with sigma of 0.02
 C24-C22 \\sim C23-C20
 with sigma of 0.02
 N6-B1 \\sim N2-B1 \\sim C4-C3 \\sim C5-C4
 with sigma of 0.02
 C9-C10 \\sim C9-C14 \\sim C14-C13 \\sim C13-C12 \\sim C12-C11 \\sim C11-C10
 with sigma of 0.02
3. Restrained planarity
 C4, C9, C10, C11, C12, C13, C14
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: F7(0.5) F8(0.5) N2(0.5) N6(0.5) C3(0.5) C4(0.5) C5(0.5) C9(0.5)
 C10(0.5) H10(0.5) C11(0.5) H11(0.5) C12(0.5) H12(0.5) C13(0.5) H13(0.5)
 C14(0.5) H14(0.5) C15(0.5) C16(0.5) C17(0.5) C18(0.5) H18A(0.5) H18B(0.5)
 H18C(0.5) C19(0.5) H19A(0.5) H19B(0.5) H19C(0.5) C20(0.5) C21(0.5) C22(0.5)
 C23(0.5) H23A(0.5) H23B(0.5) H23C(0.5) C24(0.5) H24A(0.5) H24B(0.5) H24C(0.5)
 B1(0.5)
7.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C26(H26), C28(H28), C30(H30)
7.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
I1 I 0.62242(3) 0.34135(6) 0.49489(4) 0.0465(2) Uani 1 1 d . U . . .
Cu2 Cu 0.50513(7) 0.52438(12) 0.39805(8) 0.0373(3) Uani 1 1 d . U . . .
F7 F 1.0427(8) 1.0956(17) 0.3123(9) 0.073(3) Uani 0.5 1 d D U P A -1
F8 F 1.0640(8) 0.8525(14) 0.3512(10) 0.071(3) Uani 0.5 1 d D U P A -1
N2 N 0.9380(16) 0.960(3) 0.4039(19) 0.048(3) Uani 0.5 1 d D U P A -1
N6 N 1.0973(17) 1.022(5) 0.484(2) 0.050(3) Uani 0.5 1 d D U P A -1
N27 N 0.5751(4) 0.7017(8) 0.3392(5) 0.0419(13) Uani 1 1 d . U . . .
N29 N 0.5672(4) 0.9126(8) 0.2255(5) 0.0406(13) Uani 1 1 d . U . . .
C3 C 0.9118(18) 0.972(5) 0.504(2) 0.045(3) Uani 0.5 1 d D U P A -1
C4 C 0.9660(15) 1.013(2) 0.608(3) 0.046(3) Uani 0.5 1 d D U P A -1
C5 C 1.065(2) 1.015(3) 0.580(2) 0.050(3) Uani 0.5 1 d D U P A -1
C9 C 0.9282(8) 1.0312(14) 0.7254(13) 0.049(2) Uani 0.5 1 d D U P A -1
C10 C 0.8814(12) 1.1570(17) 0.7538(12) 0.057(3) Uani 0.5 1 d D U P A -1
H10 H 0.869863 1.232817 0.700973 0.068 Uiso 0.5 1 calc R . P A -1
C11 C 0.8509(13) 1.1752(18) 0.8578(12) 0.058(3) Uani 0.5 1 d D U P A -1
H11 H 0.821669 1.263736 0.878733 0.070 Uiso 0.5 1 calc R . P A -1
C12 C 0.8650(12) 1.0595(17) 0.9282(14) 0.060(3) Uani 0.5 1 d D U P A -1
H12 H 0.844015 1.070135 0.999284 0.072 Uiso 0.5 1 calc R . P A -1
C13 C 0.9056(11) 0.9339(19) 0.9054(11) 0.058(3) Uani 0.5 1 d D U P A -1
H13 H 0.909989 0.855039 0.956648 0.070 Uiso 0.5 1 calc R . P A -1
C14 C 0.9419(11) 0.9203(17) 0.8034(11) 0.051(3) Uani 0.5 1 d D U P A -1
H14 H 0.976131 0.834665 0.787275 0.061 Uiso 0.5 1 calc R . P A -1
C15 C 0.8191(17) 0.941(4) 0.496(2) 0.045(3) Uani 0.5 1 d D U P A -1
C16 C 0.7919(18) 0.918(4) 0.385(2) 0.044(3) Uani 0.5 1 d D U P . .
C17 C 0.8681(17) 0.932(3) 0.3237(17) 0.044(3) Uani 0.5 1 d D U P A -1
C18 C 0.7617(16) 0.950(5) 0.592(2) 0.053(6) Uani 0.5 1 d D U P A -1
H18A H 0.795695 0.909793 0.656623 0.080 Uiso 0.5 1 calc GR . P A -1
H18B H 0.705477 0.893267 0.576715 0.080 Uiso 0.5 1 calc GR . P A -1
H18C H 0.746227 1.054121 0.605241 0.080 Uiso 0.5 1 calc GR . P A -1
C19 C 0.8663(19) 0.910(3) 0.2040(18) 0.045(4) Uani 0.5 1 d D U P A -1
H19A H 0.883909 1.001617 0.168684 0.068 Uiso 0.5 1 calc GR . P A -1
H19B H 0.804570 0.881127 0.176374 0.068 Uiso 0.5 1 calc GR . P A -1
H19C H 0.909417 0.830845 0.187860 0.068 Uiso 0.5 1 calc GR . P A -1
C20 C 1.1919(19) 1.051(4) 0.485(2) 0.051(4) Uani 0.5 1 d D U P A -1
C21 C 1.2169(18) 1.078(5) 0.595(2) 0.050(4) Uani 0.5 1 d D U P . .
C22 C 1.137(2) 1.059(4) 0.6495(18) 0.054(4) Uani 0.5 1 d D U P A -1
C23 C 1.2607(19) 1.061(5) 0.402(3) 0.059(6) Uani 0.5 1 d D U P A -1
H23A H 1.256346 0.973249 0.354861 0.088 Uiso 0.5 1 calc GR . P A -1
H23B H 1.322127 1.067176 0.438055 0.088 Uiso 0.5 1 calc GR . P A -1
H23C H 1.248770 1.150022 0.357113 0.088 Uiso 0.5 1 calc GR . P A -1
C24 C 1.126(2) 1.062(5) 0.769(2) 0.067(7) Uani 0.5 1 d D U P A -1
H24A H 1.095030 1.154193 0.787711 0.101 Uiso 0.5 1 calc GR . P A -1
H24B H 1.186225 1.057984 0.808147 0.101 Uiso 0.5 1 calc GR . P A -1
H24C H 1.089292 0.977223 0.789532 0.101 Uiso 0.5 1 calc GR . P A -1
C25 C 0.6974(6) 0.8748(10) 0.3483(7) 0.0475(16) Uani 1 1 d . U . . .
C26 C 0.6571(5) 0.7442(9) 0.3797(6) 0.0452(16) Uani 1 1 d . U . . .
H26 H 0.689363 0.682999 0.432105 0.054 Uiso 1 1 calc R . . . .
C28 C 0.5329(5) 0.7896(9) 0.2645(6) 0.0391(14) Uani 1 1 d . U . . .
H28 H 0.473333 0.761487 0.236946 0.047 Uiso 1 1 calc R . . . .
C30 C 0.6480(5) 0.9567(9) 0.2687(6) 0.0433(16) Uani 1 1 d . U . . .
H30 H 0.672929 1.047006 0.244365 0.052 Uiso 1 1 calc R . . . .
B1 B 1.0366(17) 0.9855(19) 0.384(4) 0.054(3) Uani 0.5 1 d D U P A -1


_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
I1 Cu2 2.6132(11) . ?
I1 Cu2 2.6512(12) 3_666 ?
Cu2 Cu2 2.557(2) 3_666 ?
Cu2 N27 2.059(7) . ?
Cu2 N29 2.057(6) 2_645 ?
F7 B1 1.34(3) . ?
F8 B1 1.34(3) . ?
N2 C3 1.312(18) . ?
N2 C17 1.40(2) . ?
N2 B1 1.501(15) . ?
N6 C5 1.308(18) . ?
N6 C20 1.41(2) . ?
N6 B1 1.501(15) . ?
N27 C26 1.327(9) . ?
N27 C28 1.334(9) . ?
N29 C28 1.322(10) . ?
N29 C30 1.326(9) . ?
C3 C4 1.507(15) . ?
C3 C15 1.38(3) . ?
C4 C5 1.507(15) . ?
C4 C9 1.59(4) . ?
C5 C22 1.37(3) . ?
C9 C10 1.384(14) . ?
C9 C14 1.391(14) . ?
C10 C11 1.392(14) . ?
C11 C12 1.363(14) . ?
C12 C13 1.320(14) . ?
C13 C14 1.399(14) . ?
C15 C16 1.42(3) . ?
C15 C18 1.49(2) . ?
C16 C17 1.39(3) . ?
C16 C21 0.29(5) 3_776 ?
C16 C25 1.48(3) . ?
C17 C19 1.48(2) . ?
C20 C21 1.39(3) . ?
C20 C23 1.49(3) . ?
C21 C22 1.40(3) . ?
C21 C25 1.46(3) 3_776 ?
C22 C24 1.48(3) . ?
C25 C26 1.385(12) . ?
C25 C30 1.390(10) . ?

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
Cu2 I1 Cu2 58.11(4) . 3_666 ?
I1 Cu2 I1 121.89(4) . 3_666 ?
Cu2 Cu2 I1 60.20(4) 3_666 3_666 ?
Cu2 Cu2 I1 61.69(4) 3_666 . ?
N27 Cu2 I1 108.85(18) . . ?
N27 Cu2 I1 101.7(2) . 3_666 ?
N27 Cu2 Cu2 122.77(18) . 3_666 ?
N29 Cu2 I1 104.13(18) 2_645 3_666 ?
N29 Cu2 I1 108.45(19) 2_645 . ?
N29 Cu2 Cu2 125.2(2) 2_645 3_666 ?
N29 Cu2 N27 111.5(3) 2_645 . ?
C3 N2 C17 115(2) . . ?
C3 N2 B1 119(3) . . ?
C17 N2 B1 125.6(17) . . ?
C5 N6 C20 115(2) . . ?
C5 N6 B1 120(3) . . ?
C20 N6 B1 125.5(18) . . ?
C26 N27 Cu2 123.7(5) . . ?
C26 N27 C28 116.9(7) . . ?
C28 N27 Cu2 119.0(5) . . ?
C28 N29 Cu2 119.3(5) . 2_655 ?
C28 N29 C30 117.3(6) . . ?
C30 N29 Cu2 123.4(5) . 2_655 ?
N2 C3 C4 130(3) . . ?
N2 C3 C15 106(2) . . ?
C15 C3 C4 124.3(18) . . ?
C3 C4 C9 126.8(14) . . ?
C5 C4 C3 106(2) . . ?
C5 C4 C9 127.0(15) . . ?
N6 C5 C4 128(3) . . ?
N6 C5 C22 104(2) . . ?
C22 C5 C4 125.0(19) . . ?
C10 C9 C4 121.6(13) . . ?
C10 C9 C14 117.9(14) . . ?
C14 C9 C4 120.5(13) . . ?
C9 C10 C11 121.6(11) . . ?
C12 C11 C10 116.5(12) . . ?
C13 C12 C11 125.2(16) . . ?
C12 C13 C14 118.0(12) . . ?
C9 C14 C13 120.5(11) . . ?
C3 C15 C16 108(2) . . ?
C3 C15 C18 123(2) . . ?
C16 C15 C18 129(2) . . ?
C15 C16 C25 122(2) . . ?
C17 C16 C15 108.9(19) . . ?
C17 C16 C25 129(2) . . ?
C21 C16 C15 43(10) 3_776 . ?
C21 C16 C17 150(10) 3_776 . ?
C21 C16 C25 80(10) 3_776 . ?
N2 C17 C19 133(2) . . ?
C16 C17 N2 102.3(19) . . ?
C16 C17 C19 124(2) . . ?
N6 C20 C23 135(2) . . ?
C21 C20 N6 104(2) . . ?
C21 C20 C23 121(2) . . ?
C20 C21 C22 105.3(19) . . ?
C20 C21 C25 132(2) . 3_776 ?
C22 C21 C25 122(2) . 3_776 ?
C5 C22 C21 112(2) . . ?
C5 C22 C24 120(2) . . ?
C21 C22 C24 128(2) . . ?
C21 C25 C16 11(2) 3_776 . ?
C26 C25 C16 123.2(15) . . ?
C26 C25 C21 119.2(16) . 3_776 ?
C26 C25 C30 115.9(7) . . ?
C30 C25 C16 120.4(15) . . ?
C30 C25 C21 124.7(17) . 3_776 ?
N27 C26 C25 122.3(7) . . ?
N29 C28 N27 125.4(6) . . ?
N29 C30 C25 122.0(7) . . ?
F7 B1 F8 116(4) . . ?
F7 B1 N2 109.2(16) . . ?
F7 B1 N6 108.2(18) . . ?
F8 B1 N2 103.0(15) . . ?
F8 B1 N6 106(2) . . ?
N6 B1 N2 115(3) . . ?

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 2.321
_oxdiff_exptl_absorpt_empirical_full_min 0.663
####################################################################### 
# 
# 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_bhasoa
_database_code_depnum_ccdc_archive 'CCDC 1920192'
loop_
_audit_author_name
_audit_author_address
'Neil Champness'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2019-06-02 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;
_nottingham_internal_coll_name   BHASOA
_nottingham_internal_coll_number 17665
_nottingham_internal_coll_client HMH/DLK
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '30.00, 120.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pcxhh4
_nottingham_internal_coll_date   25/04/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 27/04/2018
_nottingham_internal_process_user pcxhh4
_nottingham_internal_solution_date 19/8/2018
_nottingham_internal_solution_user Pcxhh4
_nottingham_internal_refinement_date 19/8/2018
_nottingham_internal_refinement_user Pcxhh4
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date ?
_nottingham_internal_validation_user ?
_nottingham_internal_archive_date ?
_refine_special_details          ?
_audit_creation_date             2018-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        BHASOA
_chemical_formula_moiety         'C27 H23 B F2 N6'
_chemical_formula_sum            'C27 H23 B F2 N6'
_chemical_formula_weight         480.32
_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'

_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                   11.2952(3)
_cell_length_b                   17.0907(6)
_cell_length_c                   12.0417(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.541(3)
_cell_angle_gamma                90
_cell_volume                     2317.27(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4634
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.5110
_cell_measurement_theta_min      3.9060
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (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 reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 -8 0.0263
1 -6 -7 0.0301
-7 1 0 0.0338
1 1 8 0.0214
-4 8 -3 0.0308
0 -10 3 0.0010
-4 9 -1 0.0267
7 3 0 0.0239
7 -1 0 0.0167

_exptl_crystal_size_max          0.069
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.042
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
-0.9915 -1.0083 -7.9862 0.0238 0.0233 1.0479
1.0130 -5.9943 -6.9889 -0.5050 0.0659 0.9149
-7.0116 0.9910 -0.0077 0.4767 -0.8133 0.1995
0.9915 1.0083 7.9862 -0.0238 -0.0233 -1.0479
-4.0069 7.9752 -2.9938 0.9000 -0.1337 0.4132
0.0017 -9.9747 2.9878 -0.8384 -0.4222 -0.2720
-4.0098 8.9754 -0.9971 0.9696 -0.1433 0.1508
7.0095 3.0003 0.0102 -0.1488 0.9552 -0.2418
7.0116 -0.9910 0.0077 -0.4767 0.8133 -0.1995

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11672
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.381
_diffrn_reflns_theta_min         3.926
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3533
_reflns_number_total             4529
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.039
_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)+(0.0403P)²+0.5265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1011
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C11(H11), C13(H13), C22(H22), C14(H14), C4(H4), C20(H20), C12(H12),
 C21(H21), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C24(H24A,H24B,H24C), C26(H26A,H26B,
 H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.43955(9) 0.76467(7) 0.50506(9) 0.0312(2) Uani 1 1 d . . . . .
F2 F 0.57744(9) 0.79379(6) 0.64634(9) 0.0317(2) Uani 1 1 d . . . . .
N1 N 0.10452(13) 0.54665(11) 0.88663(12) 0.0342(4) Uani 1 1 d . . . . .
N2 N 0.26830(15) 0.51759(13) 1.01717(13) 0.0419(4) Uani 1 1 d . . . . .
N3 N 0.49042(12) 0.66476(8) 0.64186(11) 0.0205(3) Uani 1 1 d . . . . .
N4 N 0.63286(12) 0.70411(8) 0.50516(11) 0.0206(3) Uani 1 1 d . . . . .
N5 N 0.90649(14) 0.68799(11) 0.10884(12) 0.0324(4) Uani 1 1 d . . . . .
N6 N 0.97367(14) 0.80530(10) 0.20196(13) 0.0329(4) Uani 1 1 d . . . . .
C1 C 0.39747(14) 0.66447(10) 0.70599(13) 0.0225(3) Uani 1 1 d . . . . .
C2 C 0.39040(14) 0.59061(10) 0.75700(13) 0.0221(3) Uani 1 1 d . . . . .
C3 C 0.30342(15) 0.56804(11) 0.83678(13) 0.0237(4) Uani 1 1 d . . . . .
C4 C 0.18107(16) 0.57071(12) 0.81356(14) 0.0279(4) Uani 1 1 d . . . . .
H4 H 0.150188 0.590303 0.743314 0.033 Uiso 1 1 calc R . . . .
C5 C 0.15385(18) 0.52027(14) 0.98352(16) 0.0378(5) Uani 1 1 d . . . . .
H5 H 0.100734 0.501111 1.034520 0.045 Uiso 1 1 calc R . . . .
C6 C 0.34169(17) 0.54263(14) 0.94320(15) 0.0358(5) Uani 1 1 d . . . . .
H6 H 0.424496 0.543108 0.964446 0.043 Uiso 1 1 calc R . . . .
C7 C 0.48341(13) 0.54431(10) 0.72433(12) 0.0205(3) Uani 1 1 d . . . . .
C8 C 0.54621(14) 0.59170(10) 0.65162(12) 0.0194(3) Uani 1 1 d . . . . .
C9 C 0.64675(13) 0.57651(10) 0.59359(12) 0.0182(3) Uani 1 1 d . . . . .
C10 C 0.71455(13) 0.50253(10) 0.61555(12) 0.0191(3) Uani 1 1 d . . . . .
C11 C 0.69320(15) 0.43672(10) 0.55003(14) 0.0242(4) Uani 1 1 d . . . . .
H11 H 0.632887 0.437824 0.490403 0.029 Uiso 1 1 calc R . . . .
C12 C 0.75951(16) 0.36897(11) 0.57096(15) 0.0286(4) Uani 1 1 d . . . . .
H12 H 0.744512 0.323893 0.525872 0.034 Uiso 1 1 calc R . . . .
C13 C 0.84733(15) 0.36755(11) 0.65767(15) 0.0273(4) Uani 1 1 d . . . . .
H13 H 0.893215 0.321519 0.671775 0.033 Uiso 1 1 calc R . . . .
C14 C 0.86861(15) 0.43290(11) 0.72394(14) 0.0275(4) Uani 1 1 d . . . . .
H14 H 0.928633 0.431577 0.783815 0.033 Uiso 1 1 calc R . . . .
C15 C 0.80246(15) 0.50030(11) 0.70307(13) 0.0240(4) Uani 1 1 d . . . . .
H15 H 0.817214 0.545144 0.748707 0.029 Uiso 1 1 calc R . . . .
C16 C 0.68704(14) 0.63061(10) 0.51880(13) 0.0195(3) Uani 1 1 d . . . . .
C17 C 0.77806(14) 0.62570(10) 0.44287(13) 0.0215(3) Uani 1 1 d . . . . .
C18 C 0.77472(14) 0.69585(10) 0.38466(13) 0.0221(3) Uani 1 1 d . . . . .
C19 C 0.84506(14) 0.71746(11) 0.29092(13) 0.0234(4) Uani 1 1 d . . . . .
C20 C 0.84535(15) 0.67064(12) 0.19645(14) 0.0277(4) Uani 1 1 d . . . . .
H20 H 0.799760 0.623874 0.193949 0.033 Uiso 1 1 calc R . . . .
C21 C 0.96658(16) 0.75501(13) 0.11761(15) 0.0327(4) Uani 1 1 d . . . . .
H21 H 1.009767 0.768556 0.055828 0.039 Uiso 1 1 calc R . . . .
C22 C 0.91230(15) 0.78561(11) 0.28927(14) 0.0275(4) Uani 1 1 d . . . . .
H22 H 0.915033 0.819471 0.351980 0.033 Uiso 1 1 calc R . . . .
C23 C 0.68653(14) 0.74381(10) 0.42690(13) 0.0223(3) Uani 1 1 d . . . . .
C24 C 0.32355(16) 0.73477(12) 0.72229(15) 0.0310(4) Uani 1 1 d . . . . .
H24A H 0.375239 0.779909 0.739618 0.046 Uiso 1 1 calc GR . . . .
H24B H 0.273681 0.725568 0.783998 0.046 Uiso 1 1 calc GR . . . .
H24C H 0.272935 0.745216 0.654003 0.046 Uiso 1 1 calc GR . . . .
C25 C 0.50575(15) 0.46074(10) 0.75563(14) 0.0249(4) Uani 1 1 d . . . . .
H25A H 0.506465 0.428915 0.687986 0.037 Uiso 1 1 calc GR . . . .
H25B H 0.442761 0.442175 0.800557 0.037 Uiso 1 1 calc GR . . . .
H25C H 0.582673 0.456285 0.798885 0.037 Uiso 1 1 calc GR . . . .
C26 C 0.86307(16) 0.56007(11) 0.42964(15) 0.0301(4) Uani 1 1 d . . . . .
H26A H 0.905730 0.548413 0.501790 0.045 Uiso 1 1 calc GR . . . .
H26B H 0.920046 0.575190 0.376210 0.045 Uiso 1 1 calc GR . . . .
H26C H 0.819239 0.513549 0.402237 0.045 Uiso 1 1 calc GR . . . .
C27 C 0.65718(16) 0.82607(11) 0.39669(15) 0.0291(4) Uani 1 1 d . . . . .
H27A H 0.572125 0.835037 0.402056 0.044 Uiso 1 1 calc GR . . . .
H27B H 0.677066 0.836129 0.320233 0.044 Uiso 1 1 calc GR . . . .
H27C H 0.702945 0.861395 0.447817 0.044 Uiso 1 1 calc GR . . . .
B1 B 0.53314(16) 0.73546(12) 0.57462(15) 0.0221(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.389(2) . ?
F2 B1 1.386(2) . ?
N1 C4 1.346(2) . ?
N1 C5 1.331(3) . ?
N2 C5 1.325(3) . ?
N2 C6 1.334(2) . ?
N3 C1 1.352(2) . ?
N3 C8 1.399(2) . ?
N3 B1 1.552(2) . ?
N4 C16 1.401(2) . ?
N4 C23 1.344(2) . ?
N4 B1 1.551(2) . ?
N5 C20 1.339(2) . ?
N5 C21 1.331(3) . ?
N6 C21 1.328(3) . ?
N6 C22 1.347(2) . ?
C1 C2 1.409(3) . ?
C1 C24 1.485(2) . ?
C3 C2 1.479(2) . ?
C3 C4 1.389(2) . ?
C3 C6 1.389(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C2 1.396(2) . ?
C7 C25 1.494(2) . ?
C8 C7 1.423(2) . ?
C9 C8 1.404(2) . ?
C9 C10 1.491(2) . ?
C10 C11 1.384(2) . ?
C10 C15 1.390(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C12 1.382(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C14 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C9 1.392(2) . ?
C16 C17 1.431(2) . ?
C17 C18 1.388(2) . ?
C17 C26 1.493(2) . ?
C18 C19 1.478(2) . ?
C18 C23 1.415(2) . ?
C19 C20 1.391(3) . ?
C19 C22 1.392(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C27 1.483(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C4 115.50(16) . . ?
C5 N2 C6 115.32(16) . . ?
C1 N3 C8 108.28(14) . . ?
C1 N3 B1 126.04(14) . . ?
C8 N3 B1 125.57(13) . . ?
C16 N4 B1 125.15(13) . . ?
C23 N4 C16 108.52(13) . . ?
C23 N4 B1 126.23(14) . . ?
C21 N5 C20 114.80(17) . . ?
C21 N6 C22 115.58(17) . . ?
N3 C1 C2 109.01(15) . . ?
N3 C1 C24 122.88(16) . . ?
C2 C1 C24 127.99(15) . . ?
C1 C2 C3 125.48(15) . . ?
C7 C2 C1 108.37(14) . . ?
C7 C2 C3 126.06(16) . . ?
C4 C3 C2 124.22(15) . . ?
C4 C3 C6 115.34(16) . . ?
C6 C3 C2 120.44(15) . . ?
N1 C4 C3 122.61(16) . . ?
N1 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
N1 C5 H5 116.2 . . ?
N2 C5 N1 127.62(17) . . ?
N2 C5 H5 116.2 . . ?
N2 C6 C3 123.48(17) . . ?
N2 C6 H6 118.3 . . ?
C3 C6 H6 118.3 . . ?
C2 C7 C8 105.88(15) . . ?
C2 C7 C25 125.92(15) . . ?
C8 C7 C25 128.11(14) . . ?
N3 C8 C7 108.45(13) . . ?
N3 C8 C9 119.99(15) . . ?
C9 C8 C7 131.56(16) . . ?
C8 C9 C10 119.53(14) . . ?
C16 C9 C8 121.19(15) . . ?
C16 C9 C10 119.24(14) . . ?
C11 C10 C9 121.61(14) . . ?
C11 C10 C15 119.46(16) . . ?
C15 C10 C9 118.93(15) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.40(16) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.69(17) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.23(17) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.03(16) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.20(16) . . ?
C14 C15 H15 119.9 . . ?
N4 C16 C17 107.88(14) . . ?
C9 C16 N4 120.61(14) . . ?
C9 C16 C17 131.47(15) . . ?
C16 C17 C26 127.79(15) . . ?
C18 C17 C16 106.24(15) . . ?
C18 C17 C26 125.94(15) . . ?
C17 C18 C19 127.36(16) . . ?
C17 C18 C23 108.09(14) . . ?
C23 C18 C19 124.48(15) . . ?
C20 C19 C18 121.15(16) . . ?
C20 C19 C22 115.67(15) . . ?
C22 C19 C18 123.17(16) . . ?
N5 C20 C19 123.48(18) . . ?
N5 C20 H20 118.3 . . ?
C19 C20 H20 118.3 . . ?
N5 C21 H21 116.0 . . ?
N6 C21 N5 128.09(16) . . ?
N6 C21 H21 116.0 . . ?
N6 C22 C19 122.37(17) . . ?
N6 C22 H22 118.8 . . ?
C19 C22 H22 118.8 . . ?
N4 C23 C18 109.21(15) . . ?
N4 C23 C27 123.09(15) . . ?
C18 C23 C27 127.65(15) . . ?
C1 C24 H24A 109.5 . . ?
C1 C24 H24B 109.5 . . ?
C1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 C25 H25A 109.5 . . ?
C7 C25 H25B 109.5 . . ?
C7 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C17 C26 H26A 109.5 . . ?
C17 C26 H26B 109.5 . . ?
C17 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
F1 B1 N3 109.95(14) . . ?
F1 B1 N4 110.47(13) . . ?
F2 B1 F1 109.71(15) . . ?
F2 B1 N3 110.28(13) . . ?
F2 B1 N4 110.05(14) . . ?
N4 B1 N3 106.35(14) . . ?

_olex2_exptl_crystal_mounting_method 'on fomblin film in micromount'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bhasob
_database_code_depnum_ccdc_archive 'CCDC 1920191'
loop_
_audit_author_name
_audit_author_address
'Neil Champness'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2019-06-02 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;
_nottingham_internal_coll_name   BHASOB
_nottingham_internal_coll_number 17682
_nottingham_internal_coll_client HMH/DLK
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '10.00, 40.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pcxhh4
_nottingham_internal_coll_date   02/05/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017-09'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 03/05/2018
_nottingham_internal_process_user pcxhh4
_nottingham_internal_solution_date 19/08/2018
_nottingham_internal_solution_user pcxhh4
_nottingham_internal_refinement_date 19/08/2018
_nottingham_internal_refinement_user pcxhh4
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date ?
_nottingham_internal_validation_user ?
_nottingham_internal_archive_date ?
_refine_special_details          ?
_audit_creation_date             2018-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        BHASOB
_chemical_formula_moiety         'C29 H25 B F2 N4'
_chemical_formula_sum            'C29 H25 B F2 N4'
_chemical_formula_weight         478.34
_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'

_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                   6.2631(5)
_cell_length_b                   11.5815(7)
_cell_length_c                   16.4310(8)
_cell_angle_alpha                90.269(4)
_cell_angle_beta                 91.458(5)
_cell_angle_gamma                105.041(6)
_cell_volume                     1150.56(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2984
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.2500
_cell_measurement_theta_min      4.7080
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (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            'dull brownish orange'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 7 -4 0.0492
1 -7 4 0.0492
-1 -5 -6 0.0622
-4 0 3 0.0447
3 -2 7 0.0290
-3 1 -7 0.0521
4 -1 3 0.0295
0 7 5 0.0431
-4 2 -2 0.0395
1 6 -3 0.0440
1 -2 -10 0.0466
1 0 10 0.0305
-3 4 5 0.0350
3 -7 0 0.0267
4 0 -4 0.0229

_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.07
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
-1.0018 6.9911 -3.9743 0.2682 0.7589 0.5939
1.0018 -6.9911 3.9743 -0.2682 -0.7589 -0.5939
-1.0016 -4.9980 -5.9956 -0.0873 0.2412 -0.9475
-3.9910 -0.0124 2.9878 -0.9827 0.3368 -0.1367
2.9997 -1.9897 6.9791 0.1814 -0.9426 0.2847
-2.9995 0.9906 -6.9814 -0.2196 0.8889 -0.4055
3.9951 -0.9872 2.9934 0.6337 -0.7684 0.2908
0.0024 6.9933 5.0018 0.0088 0.0606 1.0748
-3.9946 1.9863 -1.9939 -0.6472 0.7591 -0.1242
0.9955 5.9979 -2.9774 0.5917 0.3794 0.6560
0.9919 -1.9943 -9.9759 0.6483 0.3912 -0.6313
1.0049 0.0022 9.9734 -0.3111 -0.7614 0.5267
-2.9920 3.9869 4.9922 -0.7264 0.2940 0.5067
2.9957 -6.9847 -0.0127 0.3527 -0.7699 -0.6401
3.9904 0.0125 -3.9851 1.0345 -0.2738 0.0909

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7918
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.908
_diffrn_reflns_theta_min         3.953
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3587
_reflns_number_total             4495
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4495
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.030
_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)+(0.0659P)²+0.1196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1271
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C16(H16), C7(H7), C21(H21), C4(H4), C12(H12), C23(H23), C5(H5),
 C6(H6), C22(H22), C14(H14), C13(H13), C15(H15)
2.b Idealised Me refined as rotating group:
 C27(H27a,H27b,H27c), C26(H26a,H26b,H26c), C28(H28a,H28b,H28c), C29(H29a,H29b,
 H29c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.39794(19) 0.56521(9) 0.93536(6) 0.0329(2) Uani 1 1 d . . . . .
F2 F 0.11260(18) 0.43381(9) 0.86904(6) 0.0322(2) Uani 1 1 d . . . . .
N1 N -0.2614(3) 1.05916(16) 0.92294(10) 0.0395(4) Uani 1 1 d . . . . .
N2 N 0.2035(2) 0.64202(12) 0.83003(8) 0.0252(3) Uani 1 1 d . . . . .
N3 N 0.4486(2) 0.51058(12) 0.79704(8) 0.0254(3) Uani 1 1 d . . . . .
N4 N 1.0418(3) 0.17121(15) 0.66794(11) 0.0388(4) Uani 1 1 d . . . . .
C1 C 0.0762(3) 0.69692(15) 0.87132(10) 0.0265(3) Uani 1 1 d . . . . .
C2 C 0.0696(3) 0.80473(15) 0.83181(10) 0.0263(3) Uani 1 1 d . . . . .
C3 C -0.0446(3) 0.89200(15) 0.86256(10) 0.0274(4) Uani 1 1 d . . . . .
C4 C -0.2640(3) 0.85714(17) 0.88634(11) 0.0321(4) Uani 1 1 d . . . . .
H4 H -0.345665 0.775734 0.882134 0.038 Uiso 1 1 calc R . . . .
C5 C -0.3618(3) 0.94318(18) 0.91632(12) 0.0364(4) Uani 1 1 d . . . . .
H5 H -0.510465 0.917256 0.933211 0.044 Uiso 1 1 calc R . . . .
C6 C -0.0507(4) 1.09150(18) 0.90008(12) 0.0384(4) Uani 1 1 d . . . . .
H6 H 0.025610 1.173793 0.904065 0.046 Uiso 1 1 calc R . . . .
C7 C 0.0630(3) 1.01308(16) 0.87108(11) 0.0324(4) Uani 1 1 d . . . . .
H7 H 0.213619 1.041495 0.857020 0.039 Uiso 1 1 calc R . . . .
C8 C 0.1979(3) 0.81343(15) 0.76289(10) 0.0261(3) Uani 1 1 d . . . . .
C9 C 0.2798(3) 0.70968(14) 0.76120(10) 0.0248(3) Uani 1 1 d . . . . .
C10 C 0.4206(3) 0.67280(14) 0.70816(10) 0.0245(3) Uani 1 1 d . . . . .
C11 C 0.4901(3) 0.74237(15) 0.63291(10) 0.0269(3) Uani 1 1 d . . . . .
C12 C 0.3504(3) 0.72683(17) 0.56460(11) 0.0344(4) Uani 1 1 d . . . . .
H12 H 0.209046 0.671369 0.565514 0.041 Uiso 1 1 calc R . . . .
C13 C 0.4169(4) 0.79226(18) 0.49486(11) 0.0385(4) Uani 1 1 d . . . . .
H13 H 0.320509 0.781833 0.448293 0.046 Uiso 1 1 calc R . . . .
C14 C 0.6225(4) 0.87224(18) 0.49303(12) 0.0392(5) Uani 1 1 d . . . . .
H14 H 0.668196 0.916020 0.444973 0.047 Uiso 1 1 calc R . . . .
C15 C 0.7617(4) 0.88882(18) 0.56079(12) 0.0395(4) Uani 1 1 d . . . . .
H15 H 0.902530 0.944826 0.559734 0.047 Uiso 1 1 calc R . . . .
C16 C 0.6957(3) 0.82330(16) 0.63089(11) 0.0327(4) Uani 1 1 d . . . . .
H16 H 0.792285 0.834249 0.677443 0.039 Uiso 1 1 calc R . . . .
C17 C 0.5020(3) 0.57304(14) 0.72467(10) 0.0253(3) Uani 1 1 d . . . . .
C18 C 0.6395(3) 0.51720(15) 0.68012(10) 0.0265(3) Uani 1 1 d . . . . .
C19 C 0.6711(3) 0.42300(15) 0.72746(10) 0.0267(3) Uani 1 1 d . . . . .
C20 C 0.7986(3) 0.33725(15) 0.70739(10) 0.0282(4) Uani 1 1 d . . . . .
C21 C 1.0044(3) 0.37233(16) 0.67150(11) 0.0326(4) Uani 1 1 d . . . . .
H21 H 1.067733 0.454218 0.660009 0.039 Uiso 1 1 calc R . . . .
C22 C 1.1165(3) 0.28744(18) 0.65260(12) 0.0373(4) Uani 1 1 d . . . . .
H22 H 1.254975 0.313718 0.627152 0.045 Uiso 1 1 calc R . . . .
C23 C 0.8456(4) 0.13814(17) 0.70299(12) 0.0361(4) Uani 1 1 d . . . . .
H23 H 0.789097 0.055930 0.715174 0.043 Uiso 1 1 calc R . . . .
C24 C 0.7190(3) 0.21542(16) 0.72280(11) 0.0316(4) Uani 1 1 d . . . . .
H24 H 0.579062 0.185809 0.746671 0.038 Uiso 1 1 calc R . . . .
C25 C 0.5504(3) 0.42133(15) 0.79935(10) 0.0272(3) Uani 1 1 d . . . . .
C26 C 0.5336(3) 0.33899(16) 0.86996(11) 0.0328(4) Uani 1 1 d . . . . .
H26A H 0.524214 0.382766 0.920370 0.049 Uiso 1 1 calc GR . . . .
H26B H 0.664683 0.307719 0.872983 0.049 Uiso 1 1 calc GR . . . .
H26C H 0.400796 0.272465 0.862867 0.049 Uiso 1 1 calc GR . . . .
C27 C -0.0273(3) 0.64928(16) 0.94890(11) 0.0314(4) Uani 1 1 d . . . . .
H27A H -0.148785 0.578065 0.937416 0.047 Uiso 1 1 calc GR . . . .
H27B H -0.084890 0.710352 0.975602 0.047 Uiso 1 1 calc GR . . . .
H27C H 0.083628 0.628040 0.984811 0.047 Uiso 1 1 calc GR . . . .
C28 C 0.2446(3) 0.91528(16) 0.70421(11) 0.0315(4) Uani 1 1 d . . . . .
H28A H 0.401694 0.957845 0.708362 0.047 Uiso 1 1 calc GR . . . .
H28B H 0.154828 0.970364 0.717335 0.047 Uiso 1 1 calc GR . . . .
H28C H 0.207706 0.884150 0.648631 0.047 Uiso 1 1 calc GR . . . .
C29 C 0.7222(3) 0.54670(17) 0.59582(11) 0.0350(4) Uani 1 1 d . . . . .
H29A H 0.603422 0.562490 0.561190 0.052 Uiso 1 1 calc GR . . . .
H29B H 0.769195 0.479109 0.573178 0.052 Uiso 1 1 calc GR . . . .
H29C H 0.847871 0.617753 0.598052 0.052 Uiso 1 1 calc GR . . . .
B1 B 0.2872(3) 0.53402(17) 0.86097(11) 0.0262(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.389(2) . ?
F2 B1 1.382(2) . ?
N1 C5 1.330(3) . ?
N1 C6 1.339(3) . ?
N2 C1 1.337(2) . ?
N2 C9 1.401(2) . ?
N2 B1 1.559(2) . ?
N3 C17 1.397(2) . ?
N3 C25 1.348(2) . ?
N3 B1 1.547(2) . ?
N4 C22 1.333(3) . ?
N4 C23 1.335(3) . ?
C1 C27 1.488(2) . ?
C2 C1 1.420(2) . ?
C2 C3 1.476(2) . ?
C2 C8 1.394(2) . ?
C3 C4 1.395(3) . ?
C3 C7 1.394(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C6 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C28 1.501(2) . ?
C9 C8 1.424(2) . ?
C9 C10 1.397(2) . ?
C11 C10 1.491(2) . ?
C11 C12 1.387(3) . ?
C11 C16 1.383(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9500 . ?
C14 C13 1.378(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(3) . ?
C15 H15 0.9500 . ?
C16 C15 1.394(3) . ?
C16 H16 0.9500 . ?
C17 C10 1.404(2) . ?
C17 C18 1.418(2) . ?
C18 C19 1.395(2) . ?
C18 C29 1.501(2) . ?
C19 C20 1.468(2) . ?
C20 C21 1.394(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C20 1.396(3) . ?
C24 C23 1.384(3) . ?
C24 H24 0.9500 . ?
C25 C19 1.416(2) . ?
C25 C26 1.494(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C6 115.82(17) . . ?
C1 N2 C9 108.60(14) . . ?
C1 N2 B1 125.49(14) . . ?
C9 N2 B1 125.09(14) . . ?
C17 N3 B1 125.86(14) . . ?
C25 N3 C17 108.48(14) . . ?
C25 N3 B1 125.54(14) . . ?
C22 N4 C23 115.93(17) . . ?
N2 C1 C2 109.61(15) . . ?
N2 C1 C27 122.16(15) . . ?
C2 C1 C27 128.15(16) . . ?
C1 C2 C3 124.78(15) . . ?
C8 C2 C1 107.27(15) . . ?
C8 C2 C3 127.87(15) . . ?
C4 C3 C2 121.71(16) . . ?
C7 C3 C2 121.66(16) . . ?
C7 C3 C4 116.61(17) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.15(17) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 124.47(18) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
N1 C6 H6 117.8 . . ?
N1 C6 C7 124.31(19) . . ?
C7 C6 H6 117.8 . . ?
C3 C7 H7 120.2 . . ?
C6 C7 C3 119.62(18) . . ?
C6 C7 H7 120.2 . . ?
C2 C8 C9 106.65(14) . . ?
C2 C8 C28 125.90(16) . . ?
C9 C8 C28 127.43(15) . . ?
N2 C9 C8 107.84(14) . . ?
C10 C9 N2 120.16(15) . . ?
C10 C9 C8 131.91(15) . . ?
C9 C10 C11 119.32(15) . . ?
C9 C10 C17 121.64(15) . . ?
C17 C10 C11 119.02(15) . . ?
C12 C11 C10 120.62(16) . . ?
C16 C11 C10 119.91(15) . . ?
C16 C11 C12 119.47(16) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.10(18) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.18(18) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.11(17) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.90(19) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 120.23(18) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
N3 C17 C10 119.90(15) . . ?
N3 C17 C18 108.11(14) . . ?
C10 C17 C18 131.98(15) . . ?
C17 C18 C29 127.17(16) . . ?
C19 C18 C17 106.70(15) . . ?
C19 C18 C29 125.99(16) . . ?
C18 C19 C20 127.60(16) . . ?
C18 C19 C25 107.45(15) . . ?
C25 C19 C20 124.91(16) . . ?
C21 C20 C19 122.16(16) . . ?
C21 C20 C24 116.27(17) . . ?
C24 C20 C19 121.58(16) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.84(17) . . ?
C22 C21 H21 120.1 . . ?
N4 C22 C21 124.03(19) . . ?
N4 C22 H22 118.0 . . ?
C21 C22 H22 118.0 . . ?
N4 C23 H23 117.8 . . ?
N4 C23 C24 124.48(18) . . ?
C24 C23 H23 117.8 . . ?
C20 C24 H24 120.3 . . ?
C23 C24 C20 119.43(18) . . ?
C23 C24 H24 120.3 . . ?
N3 C25 C19 109.24(15) . . ?
N3 C25 C26 122.42(16) . . ?
C19 C25 C26 128.33(16) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 C27 H27A 109.5 . . ?
C1 C27 H27B 109.5 . . ?
C1 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C8 C28 H28A 109.5 . . ?
C8 C28 H28B 109.5 . . ?
C8 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C18 C29 H29A 109.5 . . ?
C18 C29 H29B 109.5 . . ?
C18 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
F1 B1 N2 108.59(14) . . ?
F1 B1 N3 110.03(15) . . ?
F2 B1 F1 110.31(14) . . ?
F2 B1 N2 110.81(15) . . ?
F2 B1 N3 110.26(14) . . ?
N3 B1 N2 106.77(13) . . ?

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cuhmhe
_database_code_depnum_ccdc_archive 'CCDC 1920194'
loop_
_audit_author_name
_audit_author_address
'Neil Champness'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2019-06-02 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;
_refine_special_details          ?
_vrf_PLAT971_cuhmhe              
;
PROBLEM: Check Calcd Resid. Dens.  0.96A   From I1              2.26 eA-3  
RESPONSE:The large residual density is around the heavy atom
iodine, which might be caused by the improper absorption correction or
the highly polarized electron densities.
;
_audit_creation_date             2019-05-21
_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         'C29 H25 B Cu2 F2 I2 N4'
_chemical_formula_sum            'C29 H25 B Cu2 F2 I2 N4'
_chemical_formula_weight         859.22
_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'
Cu Cu -1.9646 0.5888 '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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.8116(11)
_cell_length_b                   10.9371(10)
_cell_length_c                   13.6945(12)
_cell_angle_alpha                89.204(7)
_cell_angle_beta                 87.705(8)
_cell_angle_gamma                78.296(8)
_cell_volume                     1437.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1948
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      71.3340
_cell_measurement_theta_min      4.5690
_shelx_estimated_absorpt_T_max   0.305
_shelx_estimated_absorpt_T_min   0.223
_exptl_absorpt_coefficient_mu    19.014
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (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 brownish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.985
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             828
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -4 1 0.0327
-6 1 -1 0.0479
6 -1 1 0.0479
3 7 0 0.0492
2 3 8 0.0429
3 3 -7 0.0550
-4 -2 7 0.0377
-3 -6 -5 0.0337
0 2 -9 0.0295
-5 -5 -3 0.0235

_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.082
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
3.9970 -3.9992 1.0193 0.3129 0.0479 0.8944
-6.0023 1.0046 -1.0263 -0.7426 -0.0567 -0.6748
6.0023 -1.0046 1.0263 0.7426 0.0567 0.6748
3.0110 6.9889 0.0092 0.7805 0.0336 -0.6611
1.9917 2.9915 8.0082 0.4074 0.9079 -0.1670
3.0182 2.9964 -6.9897 0.5826 -0.7859 -0.1763
-4.0178 -1.9967 6.9850 -0.6615 0.8020 -0.0456
-3.0013 -5.9882 -5.0105 -0.7122 -0.5874 0.4956
0.0178 2.0010 -9.0023 0.1339 -0.9951 -0.3245
-5.0052 -4.9883 -3.0192 -0.9300 -0.3386 0.1975

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_av_unetI/netI     0.1241
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9947
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.606
_diffrn_reflns_theta_min         4.128
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3742
_reflns_number_total             5588
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         2.760
_refine_diff_density_min         -1.252
_refine_diff_density_rms         0.238
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5588
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0758
_refine_ls_restrained_S_all      1.049
_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)+(0.0849P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.1993
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C24(H24), C25(H25), C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C21(H21A,H21B,H21C), C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
I1 I -0.12051(8) -0.02111(7) 0.14492(5) 0.0317(2) Uani 1 1 d . . . . .
I2 I -0.23979(10) 0.29996(8) -0.04292(6) 0.0413(3) Uani 1 1 d . . . . .
Cu1 Cu -0.0854(2) 0.20041(19) 0.08932(14) 0.0388(5) Uani 1 1 d . . . . .
Cu2 Cu 0.8787(2) 1.05289(18) 0.95614(13) 0.0335(4) Uani 1 1 d . . . . .
F1 F 0.0969(8) 0.8689(6) 0.5394(5) 0.0318(15) Uani 1 1 d . . . . .
F2 F 0.2812(9) 0.8604(7) 0.4336(5) 0.0360(17) Uani 1 1 d . . . . .
N1 N 0.0075(12) 0.2910(9) 0.1815(7) 0.030(2) Uani 1 1 d . . . . .
N2 N 0.2114(10) 0.6669(9) 0.4797(7) 0.0239(19) Uani 1 1 d . . . . .
N3 N 0.3265(10) 0.7816(9) 0.5972(7) 0.0251(19) Uani 1 1 d . . . . .
N4 N 0.7455(10) 0.9719(9) 0.8824(8) 0.028(2) Uani 1 1 d . . . . .
C1 C 0.0745(16) 0.7312(11) 0.3312(9) 0.037(3) Uani 1 1 d . . . . .
H1A H 0.049807 0.812187 0.364036 0.056 Uiso 1 1 calc GR . . . .
H1B H -0.010351 0.706093 0.310853 0.056 Uiso 1 1 calc GR . . . .
H1C H 0.135182 0.738100 0.273613 0.056 Uiso 1 1 calc GR . . . .
C2 C 0.1483(14) 0.6367(11) 0.3991(8) 0.029(3) Uani 1 1 d . . . . .
C3 C 0.1600(13) 0.5050(11) 0.3973(9) 0.028(2) Uani 1 1 d . . . . .
C4 C 0.1057(12) 0.4336(10) 0.3217(9) 0.026(2) Uani 1 1 d . . . . .
C5 C 0.1185(13) 0.4604(11) 0.2234(8) 0.029(2) Uani 1 1 d . . . . .
H5 H 0.160562 0.527764 0.202543 0.035 Uiso 1 1 calc R . . . .
C6 C 0.0685(13) 0.3871(12) 0.1534(8) 0.031(3) Uani 1 1 d . . . . .
H6 H 0.078067 0.405776 0.085833 0.037 Uiso 1 1 calc R . . . .
C7 C -0.0023(13) 0.2664(11) 0.2768(11) 0.034(3) Uani 1 1 d . . . . .
H7 H -0.043118 0.197787 0.296216 0.041 Uiso 1 1 calc R . . . .
C8 C 0.0425(13) 0.3332(11) 0.3494(9) 0.029(2) Uani 1 1 d . . . . .
H8 H 0.031037 0.312033 0.416365 0.034 Uiso 1 1 calc R . . . .
C9 C 0.2323(12) 0.4536(11) 0.4783(8) 0.026(2) Uani 1 1 d . . . . .
C10 C 0.2791(15) 0.3172(11) 0.5016(9) 0.034(3) Uani 1 1 d . . . . .
H10A H 0.377707 0.300241 0.517474 0.051 Uiso 1 1 calc GR . . . .
H10B H 0.266574 0.267481 0.444873 0.051 Uiso 1 1 calc GR . . . .
H10C H 0.223603 0.294805 0.557631 0.051 Uiso 1 1 calc GR . . . .
C11 C 0.2616(13) 0.5565(11) 0.5316(8) 0.028(2) Uani 1 1 d . . . . .
C12 C 0.3312(12) 0.5598(11) 0.6181(9) 0.027(2) Uani 1 1 d . . . . .
C13 C 0.3632(12) 0.4462(11) 0.6808(9) 0.028(2) Uani 1 1 d . . . . .
C14 C 0.4910(13) 0.3642(12) 0.6737(9) 0.029(2) Uani 1 1 d . . . . .
H14 H 0.559232 0.378177 0.625927 0.035 Uiso 1 1 calc R . . . .
C15 C 0.5199(16) 0.2614(13) 0.7361(10) 0.039(3) Uani 1 1 d . . . . .
H15 H 0.607192 0.204996 0.730389 0.047 Uiso 1 1 calc R . . . .
C16 C 0.4209(16) 0.2414(12) 0.8067(11) 0.040(3) Uani 1 1 d . . . . .
H16 H 0.441669 0.173040 0.850881 0.048 Uiso 1 1 calc R . . . .
C17 C 0.2927(17) 0.3209(13) 0.8124(11) 0.044(3) Uani 1 1 d . . . . .
H17 H 0.223906 0.304873 0.858888 0.053 Uiso 1 1 calc R . . . .
C18 C 0.2627(16) 0.4243(12) 0.7512(9) 0.036(3) Uani 1 1 d . . . . .
H18 H 0.174828 0.479888 0.756851 0.043 Uiso 1 1 calc R . . . .
C19 C 0.3651(12) 0.6699(11) 0.6501(8) 0.026(2) Uani 1 1 d . . . . .
C20 C 0.4481(13) 0.6941(11) 0.7297(8) 0.027(2) Uani 1 1 d . . . . .
C21 C 0.5096(14) 0.6028(11) 0.8056(10) 0.034(3) Uani 1 1 d . . . . .
H21A H 0.434935 0.572593 0.842173 0.051 Uiso 1 1 calc GR . . . .
H21B H 0.561424 0.643586 0.850539 0.051 Uiso 1 1 calc GR . . . .
H21C H 0.572801 0.532250 0.774130 0.051 Uiso 1 1 calc GR . . . .
C22 C 0.4582(13) 0.8163(11) 0.7207(9) 0.030(2) Uani 1 1 d . . . . .
C23 C 0.5503(13) 0.8791(11) 0.7778(9) 0.029(2) Uani 1 1 d . . . . .
C24 C 0.5464(14) 0.8749(12) 0.8787(9) 0.032(3) Uani 1 1 d . . . . .
H24 H 0.478034 0.839656 0.913814 0.038 Uiso 1 1 calc R . . . .
C25 C 0.6447(14) 0.9234(12) 0.9278(9) 0.032(3) Uani 1 1 d . . . . .
H25 H 0.640319 0.922048 0.997200 0.039 Uiso 1 1 calc R . . . .
C26 C 0.7466(13) 0.9789(11) 0.7860(9) 0.030(2) Uani 1 1 d . . . . .
H26 H 0.813639 1.018141 0.753357 0.036 Uiso 1 1 calc R . . . .
C27 C 0.6524(13) 0.9307(11) 0.7291(8) 0.027(2) Uani 1 1 d . . . . .
H27 H 0.658785 0.933523 0.659740 0.032 Uiso 1 1 calc R . . . .
C28 C 0.3818(13) 0.8699(11) 0.6385(8) 0.025(2) Uani 1 1 d . . . . .
C29 C 0.3525(14) 1.0014(11) 0.6056(9) 0.034(3) Uani 1 1 d . . . . .
H29A H 0.408194 1.009931 0.545850 0.050 Uiso 1 1 calc GR . . . .
H29B H 0.376427 1.054308 0.656766 0.050 Uiso 1 1 calc GR . . . .
H29C H 0.253302 1.027257 0.592415 0.050 Uiso 1 1 calc GR . . . .
B1 B 0.2270(15) 0.8027(13) 0.5111(10) 0.028(3) 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
I1 Cu1 2.614(2) . ?
I1 Cu2 2.661(2) 2_666 ?
I1 Cu2 2.698(2) 1_444 ?
I2 Cu1 2.501(2) . ?
I2 Cu2 2.716(2) 1_444 ?
Cu1 Cu2 2.533(2) 1_444 ?
Cu1 N1 1.974(9) . ?
Cu2 Cu2 2.742(4) 2_777 ?
Cu2 N4 2.028(10) . ?
F1 B1 1.377(17) . ?
F2 B1 1.372(15) . ?
N1 C6 1.356(16) . ?
N1 C7 1.333(18) . ?
N2 C2 1.363(14) . ?
N2 C11 1.403(16) . ?
N2 B1 1.590(15) . ?
N3 C19 1.403(16) . ?
N3 C28 1.341(14) . ?
N3 B1 1.546(16) . ?
N4 C25 1.342(16) . ?
N4 C26 1.320(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.477(18) . ?
C2 C3 1.423(16) . ?
C3 C4 1.484(16) . ?
C3 C9 1.391(17) . ?
C4 C5 1.380(17) . ?
C4 C8 1.407(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.421(16) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.379(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.503(17) . ?
C9 C11 1.433(16) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.395(17) . ?
C12 C13 1.488(16) . ?
C12 C19 1.393(16) . ?
C13 C14 1.386(19) . ?
C13 C18 1.404(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.39(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.38(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.446(15) . ?
C20 C21 1.489(18) . ?
C20 C22 1.364(17) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.491(16) . ?
C22 C28 1.429(18) . ?
C23 C24 1.382(17) . ?
C23 C27 1.390(18) . ?
C24 H24 0.9500 . ?
C24 C25 1.390(17) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.417(16) . ?
C27 H27 0.9500 . ?
C28 C29 1.476(17) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cu1 I1 Cu2 72.97(7) . 2_666 ?
Cu1 I1 Cu2 56.94(6) . 1_444 ?
Cu2 I1 Cu2 61.55(7) 2_666 1_444 ?
Cu1 I2 Cu2 57.92(6) . 1_444 ?
I2 Cu1 I1 115.10(7) . . ?
I2 Cu1 Cu2 65.30(7) . 1_444 ?
Cu2 Cu1 I1 63.20(6) 1_444 . ?
N1 Cu1 I1 116.4(3) . . ?
N1 Cu1 I2 125.1(3) . . ?
N1 Cu1 Cu2 161.0(4) . 1_444 ?
I1 Cu2 I1 118.45(7) 2_666 1_666 ?
I1 Cu2 I2 105.76(7) 1_666 1_666 ?
I1 Cu2 I2 108.72(7) 2_666 1_666 ?
I1 Cu2 Cu2 58.56(7) 1_666 2_777 ?
I1 Cu2 Cu2 59.89(7) 2_666 2_777 ?
I2 Cu2 Cu2 125.35(10) 1_666 2_777 ?
Cu1 Cu2 I1 59.87(6) 1_666 1_666 ?
Cu1 Cu2 I1 101.84(8) 1_666 2_666 ?
Cu1 Cu2 I2 56.78(7) 1_666 1_666 ?
Cu1 Cu2 Cu2 72.85(9) 1_666 2_777 ?
N4 Cu2 I1 108.7(3) . 2_666 ?
N4 Cu2 I1 109.7(3) . 1_666 ?
N4 Cu2 I2 104.6(3) . 1_666 ?
N4 Cu2 Cu1 148.4(3) . 1_666 ?
N4 Cu2 Cu2 130.0(3) . 2_777 ?
C6 N1 Cu1 122.7(8) . . ?
C7 N1 Cu1 119.2(8) . . ?
C7 N1 C6 117.7(10) . . ?
C2 N2 C11 108.2(9) . . ?
C2 N2 B1 126.8(10) . . ?
C11 N2 B1 125.0(9) . . ?
C19 N3 B1 125.7(9) . . ?
C28 N3 C19 108.6(9) . . ?
C28 N3 B1 125.4(10) . . ?
C25 N4 Cu2 122.5(8) . . ?
C26 N4 Cu2 119.4(8) . . ?
C26 N4 C25 117.7(10) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N2 C2 C1 123.0(11) . . ?
N2 C2 C3 108.7(10) . . ?
C3 C2 C1 128.2(10) . . ?
C2 C3 C4 126.1(11) . . ?
C9 C3 C2 108.4(10) . . ?
C9 C3 C4 125.4(11) . . ?
C5 C4 C3 121.8(10) . . ?
C5 C4 C8 118.3(11) . . ?
C8 C4 C3 119.9(11) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(11) . . ?
C6 C5 H5 120.1 . . ?
N1 C6 C5 121.1(11) . . ?
N1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
N1 C7 H7 117.6 . . ?
N1 C7 C8 124.9(11) . . ?
C8 C7 H7 117.6 . . ?
C4 C8 H8 120.9 . . ?
C7 C8 C4 118.2(11) . . ?
C7 C8 H8 120.9 . . ?
C3 C9 C10 126.9(10) . . ?
C3 C9 C11 106.2(10) . . ?
C11 C9 C10 126.8(11) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C9 108.4(10) . . ?
C12 C11 N2 120.5(10) . . ?
C12 C11 C9 131.0(11) . . ?
C11 C12 C13 119.9(10) . . ?
C19 C12 C11 121.2(11) . . ?
C19 C12 C13 118.9(11) . . ?
C14 C13 C12 121.7(11) . . ?
C14 C13 C18 119.4(11) . . ?
C18 C13 C12 118.8(12) . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.3(11) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(14) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(13) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.9(13) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 120.2 . . ?
C17 C18 C13 119.5(14) . . ?
C17 C18 H18 120.2 . . ?
N3 C19 C20 107.7(9) . . ?
C12 C19 N3 120.7(10) . . ?
C12 C19 C20 131.4(11) . . ?
C19 C20 C21 126.4(11) . . ?
C22 C20 C19 106.0(11) . . ?
C22 C20 C21 127.6(11) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 C23 125.5(12) . . ?
C20 C22 C28 109.0(11) . . ?
C28 C22 C23 125.0(11) . . ?
C24 C23 C22 121.0(12) . . ?
C24 C23 C27 119.0(11) . . ?
C27 C23 C22 119.5(11) . . ?
C23 C24 H24 120.8 . . ?
C23 C24 C25 118.5(12) . . ?
C25 C24 H24 120.8 . . ?
N4 C25 C24 123.6(12) . . ?
N4 C25 H25 118.2 . . ?
C24 C25 H25 118.2 . . ?
N4 C26 H26 118.5 . . ?
N4 C26 C27 123.0(11) . . ?
C27 C26 H26 118.5 . . ?
C23 C27 C26 118.0(11) . . ?
C23 C27 H27 121.0 . . ?
C26 C27 H27 121.0 . . ?
N3 C28 C22 108.6(10) . . ?
N3 C28 C29 122.7(11) . . ?
C22 C28 C29 128.5(10) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
F1 B1 N2 108.0(10) . . ?
F1 B1 N3 111.7(10) . . ?
F2 B1 F1 110.6(11) . . ?
F2 B1 N2 109.5(9) . . ?
F2 B1 N3 111.6(10) . . ?
N3 B1 N2 105.3(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
