# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_jh367
_database_code_depnum_ccdc_archive 'CCDC 1585618'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2017-12-26 downloaded from the CCDC.
;
#============================================================================== 
_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H30 B2 N6 O2'
_chemical_formula_weight         360.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.3610(17)
_cell_length_b                   9.2410(18)
_cell_length_c                   23.393(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.30(3)
_cell_angle_gamma                90
_cell_volume                     1807.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120
_cell_measurement_reflns_used    1017
_cell_measurement_theta_min      1
_cell_measurement_theta_max      26

_exptl_crystal_description       cubic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'NONIUS KAPPA CCD'
_diffrn_measurement_method       'O-Scan    '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10003
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.370
_diffrn_reflns_theta_max         30.092
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5281
_reflns_number_gt                4233
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'COLLECT (Bruker AXS, 1997-2009)'
_computing_cell_refinement       'DENZO/SCALEPACK (Bruker AXS, 1997-2009)'
_computing_data_reduction        'DENZO/SCALEPACK (Bruker AXS, 1997-2009)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick 2016)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'XPMA (Zsolnai, Huttner, 1994)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0831P)²+0.6591P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5281
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1516
_refine_ls_wR_factor_gt          0.1397
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45116(12) 0.13022(11) 0.66677(4) 0.0316(2) Uani 1 1 d . . . . .
O2 O 0.88395(11) 0.20251(10) 0.63235(4) 0.0258(2) Uani 1 1 d . . . . .
N1 N 0.46047(12) 0.25568(13) 0.57297(5) 0.0253(2) Uani 1 1 d . . . . .
N2 N 0.71916(12) 0.30742(12) 0.55390(4) 0.0225(2) Uani 1 1 d . . . . .
N3 N 0.53667(15) 0.29083(14) 0.47678(5) 0.0307(3) Uani 1 1 d . . . . .
N4 N 0.49216(12) 0.38760(12) 0.67012(5) 0.0231(2) Uani 1 1 d . . . . .
N5 N 0.75548(12) 0.42817(12) 0.65384(4) 0.0221(2) Uani 1 1 d . . . . .
N6 N 0.61342(13) 0.59417(12) 0.71102(5) 0.0250(2) Uani 1 1 d . . . . .
B1 B 0.53136(17) 0.24713(16) 0.63595(6) 0.0233(3) Uani 1 1 d . . . . .
B2 B 0.73547(16) 0.28190(16) 0.62105(6) 0.0215(3) Uani 1 1 d . . . . .
C1 C 0.57116(15) 0.28578(14) 0.53375(5) 0.0227(2) Uani 1 1 d . . . . .
C2 C 0.29305(16) 0.23452(18) 0.55729(7) 0.0341(3) Uani 1 1 d . . . . .
H2A H 0.235785 0.325277 0.561069 0.041 Uiso 1 1 calc R U . . .
H2B H 0.244833 0.164825 0.582977 0.041 Uiso 1 1 calc R U . . .
C3 C 0.27904(18) 0.1804(2) 0.49608(8) 0.0421(4) Uani 1 1 d . . . . .
H3A H 0.321415 0.082900 0.493465 0.050 Uiso 1 1 calc R U . . .
H3B H 0.167460 0.178044 0.484544 0.050 Uiso 1 1 calc R U . . .
C4 C 0.37130(19) 0.27975(19) 0.45697(7) 0.0403(4) Uani 1 1 d . . . . .
H4A H 0.368723 0.242042 0.418283 0.048 Uiso 1 1 calc R U . . .
H4B H 0.322302 0.374892 0.456720 0.048 Uiso 1 1 calc R U . . .
C5 C 0.6557(2) 0.34098(17) 0.43616(6) 0.0355(3) Uani 1 1 d . . . . .
H5A H 0.651734 0.445656 0.433423 0.043 Uiso 1 1 calc R U . . .
H5B H 0.632833 0.301118 0.398645 0.043 Uiso 1 1 calc R U . . .
C6 C 0.82087(19) 0.29384(17) 0.45560(6) 0.0344(3) Uani 1 1 d . . . . .
H6A H 0.901081 0.333663 0.430251 0.041 Uiso 1 1 calc R U . . .
H6B H 0.828696 0.189157 0.454381 0.041 Uiso 1 1 calc R U . . .
C7 C 0.85017(16) 0.34707(16) 0.51629(6) 0.0277(3) Uani 1 1 d . . . . .
H7A H 0.948947 0.305627 0.530787 0.033 Uiso 1 1 calc R U . . .
H7B H 0.861957 0.451493 0.516011 0.033 Uiso 1 1 calc R U . . .
C8 C 0.62020(14) 0.47244(13) 0.67910(5) 0.0209(2) Uani 1 1 d . . . . .
C9 C 0.33798(15) 0.42401(16) 0.69490(6) 0.0303(3) Uani 1 1 d . . . . .
H9A H 0.278625 0.335879 0.702367 0.036 Uiso 1 1 calc R U . . .
H9B H 0.276790 0.481621 0.667898 0.036 Uiso 1 1 calc R U . . .
C10 C 0.35874(18) 0.50738(17) 0.74982(6) 0.0332(3) Uani 1 1 d . . . . .
H10A H 0.255242 0.540085 0.763195 0.040 Uiso 1 1 calc R U . . .
H10B H 0.404735 0.444781 0.778843 0.040 Uiso 1 1 calc R U . . .
C11 C 0.46637(16) 0.63587(15) 0.74061(6) 0.0274(3) Uani 1 1 d . . . . .
H11A H 0.410055 0.708156 0.718173 0.033 Uiso 1 1 calc R U . . .
H11B H 0.493520 0.678576 0.777274 0.033 Uiso 1 1 calc R U . . .
C12 C 0.75724(16) 0.67927(16) 0.72388(6) 0.0292(3) Uani 0.840(5) 1 d . . P A 1
H12A H 0.798404 0.651654 0.761156 0.035 Uiso 0.840(5) 1 calc R U P A 1
H12B H 0.729312 0.781079 0.725334 0.035 Uiso 0.840(5) 1 calc R U P A 1
C13 C 0.88540(18) 0.65678(18) 0.67971(8) 0.0271(5) Uani 0.840(5) 1 d . . P A 1
H13A H 0.855962 0.706571 0.644695 0.033 Uiso 0.840(5) 1 calc R U P A 1
H13B H 0.985514 0.697275 0.693425 0.033 Uiso 0.840(5) 1 calc R U P A 1
C14 C 0.90662(16) 0.49786(16) 0.66775(7) 0.0321(3) Uani 0.840(5) 1 d . . P A 1
H14A H 0.979918 0.485734 0.636100 0.039 Uiso 0.840(5) 1 calc R U P A 1
H14B H 0.953405 0.451394 0.701043 0.039 Uiso 0.840(5) 1 calc R U P A 1
C22 C 0.75724(16) 0.67927(16) 0.72388(6) 0.0292(3) Uani 0.160(5) 1 d . . P A 2
H22A H 0.757861 0.705528 0.764026 0.035 Uiso 0.160(5) 1 calc R U P A 2
H22B H 0.755668 0.767766 0.701583 0.035 Uiso 0.160(5) 1 calc R U P A 2
C23 C 0.9082(12) 0.5937(10) 0.7102(4) 0.033(3) Uani 0.160(5) 1 d . . P A 2
H23A H 0.992135 0.663121 0.702044 0.039 Uiso 0.160(5) 1 calc R U P A 2
H23B H 0.939743 0.542672 0.744672 0.039 Uiso 0.160(5) 1 calc R U P A 2
C24 C 0.90662(16) 0.49786(16) 0.66775(7) 0.0321(3) Uani 0.160(5) 1 d . . P A 2
H24A H 0.983440 0.422656 0.677001 0.039 Uiso 0.160(5) 1 calc R U P A 2
H24B H 0.944465 0.546153 0.633576 0.039 Uiso 0.160(5) 1 calc R U P A 2
C15 C 0.4690(2) -0.00970(17) 0.64453(8) 0.0393(4) Uani 1 1 d . . . . .
H15A H 0.472261 -0.005109 0.603558 0.059 Uiso 1 1 calc R U . . .
H15B H 0.380259 -0.068505 0.656136 0.059 Uiso 1 1 calc R U . . .
H15C H 0.566690 -0.051287 0.658680 0.059 Uiso 1 1 calc R U . . .
C16 C 0.89725(19) 0.06309(16) 0.60943(7) 0.0352(3) Uani 1 1 d . . . . .
H16A H 0.879691 0.066825 0.568872 0.053 Uiso 1 1 calc R U . . .
H16B H 0.818861 0.001095 0.626587 0.053 Uiso 1 1 calc R U . . .
H16C H 1.002330 0.025764 0.617127 0.053 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.4019(18) . ?
O1 B1 1.4633(18) . ?
O2 C16 1.4001(17) . ?
O2 B2 1.4648(17) . ?
N1 C1 1.3358(17) . ?
N1 C2 1.4584(16) . ?
N1 B1 1.5872(18) . ?
N2 C1 1.3368(16) . ?
N2 C7 1.4554(16) . ?
N2 B2 1.5937(17) . ?
N3 C1 1.3631(17) . ?
N3 C5 1.455(2) . ?
N3 C4 1.4595(19) . ?
N4 C8 1.3426(16) . ?
N4 C9 1.4557(16) . ?
N4 B1 1.5602(18) . ?
N5 C8 1.3427(16) . ?
N5 C24 1.4536(16) . ?
N5 C14 1.4536(16) . ?
N5 B2 1.5627(18) . ?
N6 C8 1.3515(16) . ?
N6 C11 1.4656(17) . ?
N6 C22 1.4667(17) . ?
N6 C12 1.4667(17) . ?
B1 B2 1.773(2) . ?
C2 C3 1.521(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.511(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.515(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.521(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.507(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.506(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.507(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.506(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C22 C23 1.525(10) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.330(9) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C15 O1 B1 116.63(11) . . ?
C16 O2 B2 117.44(10) . . ?
C1 N1 C2 121.52(12) . . ?
C1 N1 B1 113.03(10) . . ?
C2 N1 B1 125.46(11) . . ?
C1 N2 C7 121.52(11) . . ?
C1 N2 B2 113.56(10) . . ?
C7 N2 B2 124.91(10) . . ?
C1 N3 C5 120.48(12) . . ?
C1 N3 C4 120.21(13) . . ?
C5 N3 C4 117.72(12) . . ?
C8 N4 C9 120.65(11) . . ?
C8 N4 B1 113.37(10) . . ?
C9 N4 B1 125.82(11) . . ?
C8 N5 C24 119.99(11) . . ?
C8 N5 C14 119.99(11) . . ?
C8 N5 B2 113.03(10) . . ?
C24 N5 B2 125.71(10) . . ?
C14 N5 B2 125.71(10) . . ?
C8 N6 C11 121.16(11) . . ?
C8 N6 C22 121.53(11) . . ?
C11 N6 C22 116.81(11) . . ?
C8 N6 C12 121.53(11) . . ?
C11 N6 C12 116.81(11) . . ?
O1 B1 N4 105.30(10) . . ?
O1 B1 N1 108.92(11) . . ?
N4 B1 N1 110.83(11) . . ?
O1 B1 B2 132.43(12) . . ?
N4 B1 B2 98.91(10) . . ?
N1 B1 B2 99.42(10) . . ?
O2 B2 N5 104.84(10) . . ?
O2 B2 N2 108.66(10) . . ?
N5 B2 N2 111.36(10) . . ?
O2 B2 B1 133.59(11) . . ?
N5 B2 B1 99.26(9) . . ?
N2 B2 B1 98.22(10) . . ?
N1 C1 N2 115.62(11) . . ?
N1 C1 N3 122.33(12) . . ?
N2 C1 N3 122.03(12) . . ?
N1 C2 C3 110.49(12) . . ?
N1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 109.45(13) . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
N3 C4 C3 109.66(12) . . ?
N3 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
N3 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N3 C5 C6 109.75(11) . . ?
N3 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
N3 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C5 C6 C7 109.21(12) . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 C6 111.39(12) . . ?
N2 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N2 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N4 C8 N5 115.22(11) . . ?
N4 C8 N6 122.47(11) . . ?
N5 C8 N6 122.31(11) . . ?
N4 C9 C10 111.06(11) . . ?
N4 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N4 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 110.33(12) . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N6 C11 C10 111.32(11) . . ?
N6 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
N6 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N6 C12 C13 111.75(11) . . ?
N6 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
N6 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 110.29(13) . . ?
C14 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
N5 C14 C13 111.75(12) . . ?
N5 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
N5 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
N6 C22 C23 111.0(3) . . ?
N6 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
N6 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C24 C23 C22 119.8(6) . . ?
C24 C23 H23A 107.4 . . ?
C22 C23 H23A 107.4 . . ?
C24 C23 H23B 107.4 . . ?
C22 C23 H23B 107.4 . . ?
H23A C23 H23B 106.9 . . ?
C23 C24 N5 117.9(4) . . ?
C23 C24 H24A 107.8 . . ?
N5 C24 H24A 107.8 . . ?
C23 C24 H24B 107.8 . . ?
N5 C24 H24B 107.8 . . ?
H24A C24 H24B 107.2 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 O1 B1 N4 -179.61(12) . . . . ?
C15 O1 B1 N1 61.48(16) . . . . ?
C15 O1 B1 B2 -61.73(19) . . . . ?
C8 N4 B1 O1 134.11(11) . . . . ?
C9 N4 B1 O1 -41.14(17) . . . . ?
C8 N4 B1 N1 -108.26(12) . . . . ?
C9 N4 B1 N1 76.49(15) . . . . ?
C8 N4 B1 B2 -4.55(13) . . . . ?
C9 N4 B1 B2 -179.81(12) . . . . ?
C1 N1 B1 O1 -142.01(11) . . . . ?
C2 N1 B1 O1 38.28(17) . . . . ?
C1 N1 B1 N4 102.60(12) . . . . ?
C2 N1 B1 N4 -77.11(16) . . . . ?
C1 N1 B1 B2 -0.77(14) . . . . ?
C2 N1 B1 B2 179.52(12) . . . . ?
C16 O2 B2 N5 177.87(11) . . . . ?
C16 O2 B2 N2 -62.97(14) . . . . ?
C16 O2 B2 B1 59.04(18) . . . . ?
C8 N5 B2 O2 -140.66(10) . . . . ?
C24 N5 B2 O2 26.41(16) . . . . ?
C14 N5 B2 O2 26.41(16) . . . . ?
C8 N5 B2 N2 102.00(12) . . . . ?
C24 N5 B2 N2 -90.92(15) . . . . ?
C14 N5 B2 N2 -90.92(15) . . . . ?
C8 N5 B2 B1 -0.67(13) . . . . ?
C24 N5 B2 B1 166.40(12) . . . . ?
C14 N5 B2 B1 166.40(12) . . . . ?
C1 N2 B2 O2 137.75(11) . . . . ?
C7 N2 B2 O2 -40.84(16) . . . . ?
C1 N2 B2 N5 -107.26(12) . . . . ?
C7 N2 B2 N5 74.15(15) . . . . ?
C1 N2 B2 B1 -3.89(13) . . . . ?
C7 N2 B2 B1 177.52(11) . . . . ?
O1 B1 B2 O2 3.4(2) . . . . ?
N4 B1 B2 O2 123.76(14) . . . . ?
N1 B1 B2 O2 -123.23(14) . . . . ?
O1 B1 B2 N5 -117.49(14) . . . . ?
N4 B1 B2 N5 2.85(11) . . . . ?
N1 B1 B2 N5 115.86(10) . . . . ?
O1 B1 B2 N2 129.15(14) . . . . ?
N4 B1 B2 N2 -110.51(10) . . . . ?
N1 B1 B2 N2 2.50(11) . . . . ?
C2 N1 C1 N2 177.87(12) . . . . ?
B1 N1 C1 N2 -1.86(16) . . . . ?
C2 N1 C1 N3 -3.6(2) . . . . ?
B1 N1 C1 N3 176.65(12) . . . . ?
C7 N2 C1 N1 -177.38(12) . . . . ?
B2 N2 C1 N1 3.98(16) . . . . ?
C7 N2 C1 N3 4.1(2) . . . . ?
B2 N2 C1 N3 -174.53(12) . . . . ?
C5 N3 C1 N1 172.53(13) . . . . ?
C4 N3 C1 N1 7.2(2) . . . . ?
C5 N3 C1 N2 -9.1(2) . . . . ?
C4 N3 C1 N2 -174.39(13) . . . . ?
C1 N1 C2 C3 27.1(2) . . . . ?
B1 N1 C2 C3 -153.21(14) . . . . ?
N1 C2 C3 C4 -52.45(18) . . . . ?
C1 N3 C4 C3 -33.83(18) . . . . ?
C5 N3 C4 C3 160.43(13) . . . . ?
C2 C3 C4 N3 55.56(16) . . . . ?
C1 N3 C5 C6 35.25(18) . . . . ?
C4 N3 C5 C6 -159.05(13) . . . . ?
N3 C5 C6 C7 -54.98(16) . . . . ?
C1 N2 C7 C6 -26.19(18) . . . . ?
B2 N2 C7 C6 152.28(12) . . . . ?
C5 C6 C7 N2 50.96(16) . . . . ?
C9 N4 C8 N5 -179.69(12) . . . . ?
B1 N4 C8 N5 4.78(16) . . . . ?
C9 N4 C8 N6 -0.04(19) . . . . ?
B1 N4 C8 N6 -175.57(11) . . . . ?
C24 N5 C8 N4 -170.27(12) . . . . ?
C14 N5 C8 N4 -170.27(12) . . . . ?
B2 N5 C8 N4 -2.38(15) . . . . ?
C24 N5 C8 N6 10.08(19) . . . . ?
C14 N5 C8 N6 10.08(19) . . . . ?
B2 N5 C8 N6 177.98(11) . . . . ?
C11 N6 C8 N4 3.67(19) . . . . ?
C22 N6 C8 N4 175.29(12) . . . . ?
C12 N6 C8 N4 175.29(12) . . . . ?
C11 N6 C8 N5 -176.71(11) . . . . ?
C22 N6 C8 N5 -5.09(19) . . . . ?
C12 N6 C8 N5 -5.09(19) . . . . ?
C8 N4 C9 C10 -28.83(18) . . . . ?
B1 N4 C9 C10 146.10(13) . . . . ?
N4 C9 C10 C11 52.67(16) . . . . ?
C8 N6 C11 C10 22.10(17) . . . . ?
C22 N6 C11 C10 -149.90(12) . . . . ?
C12 N6 C11 C10 -149.90(12) . . . . ?
C9 C10 C11 N6 -49.26(16) . . . . ?
C8 N6 C12 C13 24.68(18) . . . . ?
C11 N6 C12 C13 -163.36(13) . . . . ?
N6 C12 C13 C14 -47.16(17) . . . . ?
C8 N5 C14 C13 -34.30(19) . . . . ?
B2 N5 C14 C13 159.45(13) . . . . ?
C12 C13 C14 N5 52.16(18) . . . . ?
C8 N6 C22 C23 -14.2(4) . . . . ?
C11 N6 C22 C23 157.8(4) . . . . ?
N6 C22 C23 C24 31.3(9) . . . . ?
C22 C23 C24 N5 -28.4(9) . . . . ?
C8 N5 C24 C23 7.3(5) . . . . ?
B2 N5 C24 C23 -159.0(5) . . . . ?

_refine_diff_density_max         0.839
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_jh124_2
_database_code_depnum_ccdc_archive 'CCDC 1585621'
_audit_update_record             
;
2017-12-19 deposited with the CCDC.
2017-12-26 downloaded from the CCDC.
;
#============================================================================== 
_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H36 B2 N8'
_chemical_formula_weight         386.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.837(3)
_cell_length_b                   9.5390(19)
_cell_length_c                   15.937(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.01(3)
_cell_angle_gamma                90
_cell_volume                     2092.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1335
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      26.0

_exptl_crystal_description       'box shaped'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'NONIUS KAPPA CCD'
_diffrn_measurement_method       'O-Scan    '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9037
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.598
_diffrn_reflns_theta_max         27.538
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4811
_reflns_number_gt                3176
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'COLLECT (Bruker AXS, 1997-2009)'
_computing_cell_refinement       'DENZO/SCALEPACK (Bruker AXS, 1997-2009)'
_computing_data_reduction        'DENZO/SCALEPACK (Bruker AXS, 1997-2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'XPMA (Zsolnai, Huttner, 1994)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0688P)²+0.3669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4811
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.63588(11) 0.19327(14) 0.08322(8) 0.0310(3) Uani 1 1 d . . . . .
N2 N 0.60317(11) 0.24447(15) -0.05563(9) 0.0306(3) Uani 1 1 d . . . . .
N3 N 0.47179(11) 0.20515(15) 0.02468(9) 0.0334(4) Uani 1 1 d . . . . .
N4 N 0.79597(11) 0.06863(16) 0.05244(8) 0.0327(4) Uani 1 1 d . . . . .
N5 N 0.76054(11) 0.11862(14) -0.08626(9) 0.0309(3) Uani 1 1 d . . . . .
N6 N 0.84544(11) -0.09049(15) -0.04857(9) 0.0339(4) Uani 1 1 d . . . . .
N7 N 0.79909(11) 0.29503(16) 0.13417(9) 0.0358(4) Uani 1 1 d . . . . .
N8 N 0.74444(11) 0.37985(14) -0.10107(9) 0.0326(4) Uani 1 1 d . . . . .
B1 B 0.74366(15) 0.2156(2) 0.06045(12) 0.0308(4) Uani 1 1 d . . . . .
B2 B 0.71754(15) 0.2542(2) -0.04790(12) 0.0301(4) Uani 1 1 d . . . . .
C1 C 0.56833(13) 0.21292(17) 0.01722(10) 0.0292(4) Uani 1 1 d . . . . .
C2 C 0.60815(14) 0.1534(2) 0.16585(11) 0.0348(4) Uani 1 1 d . . . . .
H2A H 0.653104 0.195462 0.209494 0.042 Uiso 1 1 calc R U . . .
H2B H 0.612741 0.052395 0.172032 0.042 Uiso 1 1 calc R U . . .
C3 C 0.50560(14) 0.1998(2) 0.17750(11) 0.0381(4) Uani 1 1 d . . . . .
H3A H 0.485509 0.158938 0.228645 0.046 Uiso 1 1 calc R U . . .
H3B H 0.503339 0.301030 0.182688 0.046 Uiso 1 1 calc R U . . .
C4 C 0.43767(14) 0.1527(2) 0.10197(11) 0.0376(4) Uani 1 1 d . . . . .
H4A H 0.434920 0.051124 0.100344 0.045 Uiso 1 1 calc R U . . .
H4B H 0.372686 0.187697 0.106911 0.045 Uiso 1 1 calc R U . . .
C5 C 0.40149(14) 0.21036(19) -0.04987(12) 0.0375(4) Uani 1 1 d . . . . .
H5A H 0.339842 0.245034 -0.034484 0.045 Uiso 1 1 calc R U . . .
H5B H 0.391205 0.116728 -0.072824 0.045 Uiso 1 1 calc R U . . .
C6 C 0.43764(14) 0.3053(2) -0.11582(11) 0.0392(5) Uani 1 1 d . . . . .
H6A H 0.393599 0.301026 -0.167277 0.047 Uiso 1 1 calc R U . . .
H6B H 0.439855 0.401354 -0.095790 0.047 Uiso 1 1 calc R U . . .
C7 C 0.53787(13) 0.2592(2) -0.13347(11) 0.0346(4) Uani 1 1 d . . . . .
H7A H 0.533272 0.170160 -0.163010 0.042 Uiso 1 1 calc R U . . .
H7B H 0.564567 0.327514 -0.169796 0.042 Uiso 1 1 calc R U . . .
C8 C 0.80091(13) 0.02985(17) -0.02781(10) 0.0299(4) Uani 1 1 d . . . . .
C9 C 0.83404(14) -0.0227(2) 0.12141(11) 0.0390(4) Uani 1 1 d . . . . .
H9A H 0.782404 -0.082837 0.137246 0.047 Uiso 1 1 calc R U . . .
H9B H 0.856948 0.033868 0.170031 0.047 Uiso 1 1 calc R U . . .
C10 C 0.91617(15) -0.1118(2) 0.09658(12) 0.0432(5) Uani 1 1 d . . . . .
H10A H 0.971785 -0.052801 0.089332 0.052 Uiso 1 1 calc R U . . .
H10B H 0.935230 -0.178693 0.141095 0.052 Uiso 1 1 calc R U . . .
C11 C 0.88623(14) -0.1885(2) 0.01626(12) 0.0395(5) Uani 1 1 d . . . . .
H11A H 0.942126 -0.235524 -0.002796 0.047 Uiso 1 1 calc R U . . .
H11B H 0.838167 -0.259041 0.025977 0.047 Uiso 1 1 calc R U . . .
C12 C 0.83972(14) -0.13699(19) -0.13680(11) 0.0364(4) Uani 1 1 d . . . . .
H12A H 0.783259 -0.196694 -0.149061 0.044 Uiso 1 1 calc R U . . .
H12B H 0.897013 -0.191687 -0.145198 0.044 Uiso 1 1 calc R U . . .
C13 C 0.83260(14) -0.01400(19) -0.19651(11) 0.0379(4) Uani 1 1 d . . . . .
H13A H 0.893902 0.036178 -0.191876 0.045 Uiso 1 1 calc R U . . .
H13B H 0.819171 -0.047129 -0.254099 0.045 Uiso 1 1 calc R U . . .
C14 C 0.75269(14) 0.08282(19) -0.17559(10) 0.0343(4) Uani 1 1 d . . . . .
H14A H 0.755039 0.168099 -0.208465 0.041 Uiso 1 1 calc R U . . .
H14B H 0.690386 0.038314 -0.191292 0.041 Uiso 1 1 calc R U . . .
C15 C 0.75634(16) 0.4265(2) 0.15684(12) 0.0433(5) Uani 1 1 d . . . . .
H15A H 0.785677 0.455912 0.211241 0.065 Uiso 1 1 calc R U . . .
H15B H 0.687740 0.414225 0.158719 0.065 Uiso 1 1 calc R U . . .
H15C H 0.767270 0.496460 0.115575 0.065 Uiso 1 1 calc R U . . .
C16 C 0.90203(14) 0.3139(2) 0.12972(12) 0.0465(5) Uani 1 1 d . . . . .
H16A H 0.912001 0.385605 0.089269 0.070 Uiso 1 1 calc R U . . .
H16B H 0.929840 0.227470 0.112800 0.070 Uiso 1 1 calc R U . . .
H16C H 0.932650 0.341014 0.184129 0.070 Uiso 1 1 calc R U . . .
C17 C 0.70319(15) 0.51184(19) -0.07769(12) 0.0411(5) Uani 1 1 d . . . . .
H17A H 0.735926 0.543122 -0.024919 0.062 Uiso 1 1 calc R U . . .
H17B H 0.635307 0.499501 -0.072098 0.062 Uiso 1 1 calc R U . . .
H17C H 0.710974 0.580457 -0.120529 0.062 Uiso 1 1 calc R U . . .
C18 C 0.84727(14) 0.3983(2) -0.10865(12) 0.0413(5) Uani 1 1 d . . . . .
H18A H 0.855552 0.465225 -0.152297 0.062 Uiso 1 1 calc R U . . .
H18B H 0.875057 0.310164 -0.122621 0.062 Uiso 1 1 calc R U . . .
H18C H 0.879228 0.431591 -0.056055 0.062 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.345(2) . ?
N1 C2 1.460(2) . ?
N1 B1 1.586(3) . ?
N2 C1 1.337(2) . ?
N2 C7 1.463(2) . ?
N2 B2 1.577(3) . ?
N3 C1 1.356(2) . ?
N3 C4 1.453(2) . ?
N3 C5 1.455(2) . ?
N4 C8 1.340(2) . ?
N4 C9 1.457(2) . ?
N4 B1 1.589(2) . ?
N5 C8 1.337(2) . ?
N5 C14 1.457(2) . ?
N5 B2 1.574(2) . ?
N6 C8 1.360(2) . ?
N6 C11 1.462(2) . ?
N6 C12 1.469(2) . ?
N7 C16 1.445(2) . ?
N7 C15 1.448(2) . ?
N7 B1 1.534(2) . ?
N8 C17 1.447(2) . ?
N8 C18 1.451(2) . ?
N8 B2 1.536(2) . ?
B1 B2 1.766(3) . ?
C2 C3 1.516(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.516(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.511(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.509(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.505(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.495(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.507(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.505(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 120.99(15) . . ?
C1 N1 B1 113.30(14) . . ?
C2 N1 B1 125.71(14) . . ?
C1 N2 C7 120.74(15) . . ?
C1 N2 B2 113.30(14) . . ?
C7 N2 B2 125.88(14) . . ?
C1 N3 C4 120.24(15) . . ?
C1 N3 C5 120.47(15) . . ?
C4 N3 C5 117.06(15) . . ?
C8 N4 C9 120.28(15) . . ?
C8 N4 B1 112.92(14) . . ?
C9 N4 B1 126.77(14) . . ?
C8 N5 C14 121.02(14) . . ?
C8 N5 B2 113.41(14) . . ?
C14 N5 B2 125.42(14) . . ?
C8 N6 C11 121.26(15) . . ?
C8 N6 C12 120.50(14) . . ?
C11 N6 C12 117.49(14) . . ?
C16 N7 C15 109.58(15) . . ?
C16 N7 B1 116.12(14) . . ?
C15 N7 B1 115.74(15) . . ?
C17 N8 C18 109.43(15) . . ?
C17 N8 B2 114.32(14) . . ?
C18 N8 B2 115.90(15) . . ?
N7 B1 N1 107.32(14) . . ?
N7 B1 N4 107.57(15) . . ?
N1 B1 N4 110.33(14) . . ?
N7 B1 B2 132.87(16) . . ?
N1 B1 B2 98.67(13) . . ?
N4 B1 B2 98.85(13) . . ?
N8 B2 N5 107.68(14) . . ?
N8 B2 N2 107.59(14) . . ?
N5 B2 N2 109.77(14) . . ?
N8 B2 B1 131.75(15) . . ?
N5 B2 B1 99.28(13) . . ?
N2 B2 B1 99.49(13) . . ?
N2 C1 N1 115.22(15) . . ?
N2 C1 N3 122.45(16) . . ?
N1 C1 N3 122.30(15) . . ?
N1 C2 C3 111.85(14) . . ?
N1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 109.07(15) . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N3 C4 C3 109.98(15) . . ?
N3 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
N3 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N3 C5 C6 110.27(15) . . ?
N3 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
N3 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C5 109.44(15) . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C6 111.59(14) . . ?
N2 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N5 C8 N4 115.51(15) . . ?
N5 C8 N6 122.14(15) . . ?
N4 C8 N6 122.34(16) . . ?
N4 C9 C10 111.26(15) . . ?
N4 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N4 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 110.63(16) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N6 C11 C10 110.13(16) . . ?
N6 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
N6 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N6 C12 C13 111.27(14) . . ?
N6 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
N6 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 109.80(15) . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N5 C14 C13 112.28(15) . . ?
N5 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
N5 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
N7 C15 H15A 109.5 . . ?
N7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N7 C16 H16A 109.5 . . ?
N7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N8 C17 H17A 109.5 . . ?
N8 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N8 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N8 C18 H18A 109.5 . . ?
N8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N7 B1 N1 174.04(15) . . . . ?
C15 N7 B1 N1 -55.37(19) . . . . ?
C16 N7 B1 N4 55.3(2) . . . . ?
C15 N7 B1 N4 -174.08(14) . . . . ?
C16 N7 B1 B2 -65.6(3) . . . . ?
C15 N7 B1 B2 65.0(3) . . . . ?
C1 N1 B1 N7 139.11(15) . . . . ?
C2 N1 B1 N7 -41.8(2) . . . . ?
C1 N1 B1 N4 -103.97(16) . . . . ?
C2 N1 B1 N4 75.2(2) . . . . ?
C1 N1 B1 B2 -1.11(17) . . . . ?
C2 N1 B1 B2 178.02(15) . . . . ?
C8 N4 B1 N7 -140.57(15) . . . . ?
C9 N4 B1 N7 41.1(2) . . . . ?
C8 N4 B1 N1 102.66(16) . . . . ?
C9 N4 B1 N1 -75.6(2) . . . . ?
C8 N4 B1 B2 -0.08(18) . . . . ?
C9 N4 B1 B2 -178.36(16) . . . . ?
C17 N8 B2 N5 175.30(15) . . . . ?
C18 N8 B2 N5 -55.99(19) . . . . ?
C17 N8 B2 N2 57.04(19) . . . . ?
C18 N8 B2 N2 -174.25(13) . . . . ?
C17 N8 B2 B1 -63.9(2) . . . . ?
C18 N8 B2 B1 64.8(2) . . . . ?
C8 N5 B2 N8 138.04(15) . . . . ?
C14 N5 B2 N8 -46.5(2) . . . . ?
C8 N5 B2 N2 -105.12(17) . . . . ?
C14 N5 B2 N2 70.4(2) . . . . ?
C8 N5 B2 B1 -1.45(19) . . . . ?
C14 N5 B2 B1 174.04(15) . . . . ?
C1 N2 B2 N8 -139.46(14) . . . . ?
C7 N2 B2 N8 44.0(2) . . . . ?
C1 N2 B2 N5 103.64(16) . . . . ?
C7 N2 B2 N5 -73.0(2) . . . . ?
C1 N2 B2 B1 0.12(17) . . . . ?
C7 N2 B2 B1 -176.48(15) . . . . ?
N7 B1 B2 N8 1.0(3) . . . . ?
N1 B1 B2 N8 124.58(19) . . . . ?
N4 B1 B2 N8 -123.12(19) . . . . ?
N7 B1 B2 N5 125.0(2) . . . . ?
N1 B1 B2 N5 -111.47(14) . . . . ?
N4 B1 B2 N5 0.82(16) . . . . ?
N7 B1 B2 N2 -123.0(2) . . . . ?
N1 B1 B2 N2 0.54(15) . . . . ?
N4 B1 B2 N2 112.83(14) . . . . ?
C7 N2 C1 N1 175.88(14) . . . . ?
B2 N2 C1 N1 -0.9(2) . . . . ?
C7 N2 C1 N3 -5.9(2) . . . . ?
B2 N2 C1 N3 177.31(15) . . . . ?
C2 N1 C1 N2 -177.81(14) . . . . ?
B1 N1 C1 N2 1.4(2) . . . . ?
C2 N1 C1 N3 4.0(2) . . . . ?
B1 N1 C1 N3 -176.86(15) . . . . ?
C4 N3 C1 N2 171.89(16) . . . . ?
C5 N3 C1 N2 9.3(2) . . . . ?
C4 N3 C1 N1 -10.0(2) . . . . ?
C5 N3 C1 N1 -172.60(15) . . . . ?
C1 N1 C2 C3 -25.3(2) . . . . ?
B1 N1 C2 C3 155.60(15) . . . . ?
N1 C2 C3 C4 50.2(2) . . . . ?
C1 N3 C4 C3 36.4(2) . . . . ?
C5 N3 C4 C3 -160.45(15) . . . . ?
C2 C3 C4 N3 -55.3(2) . . . . ?
C1 N3 C5 C6 -34.0(2) . . . . ?
C4 N3 C5 C6 162.90(15) . . . . ?
N3 C5 C6 C7 53.85(19) . . . . ?
C1 N2 C7 C6 27.9(2) . . . . ?
B2 N2 C7 C6 -155.73(16) . . . . ?
C5 C6 C7 N2 -51.2(2) . . . . ?
C14 N5 C8 N4 -174.09(15) . . . . ?
B2 N5 C8 N4 1.6(2) . . . . ?
C14 N5 C8 N6 7.0(3) . . . . ?
B2 N5 C8 N6 -177.29(15) . . . . ?
C9 N4 C8 N5 177.49(16) . . . . ?
B1 N4 C8 N5 -0.9(2) . . . . ?
C9 N4 C8 N6 -3.6(3) . . . . ?
B1 N4 C8 N6 177.98(15) . . . . ?
C11 N6 C8 N5 -177.90(16) . . . . ?
C12 N6 C8 N5 -8.1(3) . . . . ?
C11 N6 C8 N4 3.3(3) . . . . ?
C12 N6 C8 N4 173.09(16) . . . . ?
C8 N4 C9 C10 28.8(2) . . . . ?
B1 N4 C9 C10 -153.02(17) . . . . ?
N4 C9 C10 C11 -52.8(2) . . . . ?
C8 N6 C11 C10 -28.1(2) . . . . ?
C12 N6 C11 C10 161.79(16) . . . . ?
C9 C10 C11 N6 51.9(2) . . . . ?
C8 N6 C12 C13 30.9(2) . . . . ?
C11 N6 C12 C13 -158.88(16) . . . . ?
N6 C12 C13 C14 -50.9(2) . . . . ?
C8 N5 C14 C13 -29.1(2) . . . . ?
B2 N5 C14 C13 155.70(16) . . . . ?
C12 C13 C14 N5 50.3(2) . . . . ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_sli409
_database_code_depnum_ccdc_archive 'CCDC 1585619'
_audit_update_record             
;
2017-12-19 deposited with the CCDC.
2017-12-26 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H26 B2 Cl2 F6 N6 O6 S2'
_chemical_formula_weight         681.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.694(3)
_cell_length_b                   15.531(3)
_cell_length_c                   22.791(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5555.2(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    120
_cell_measurement_reflns_used    8133
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      30.11

_exptl_crystal_description       'box shaped'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_F_000             2784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.470
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_process_details   SADBAS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'NONIUS KAPPA CCD'
_diffrn_measurement_method       'O-Scan    '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            107143
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_av_R_equivalents  0.1234
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.050
_diffrn_reflns_theta_max         30.112
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8130
_reflns_number_gt                4785
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'COLLECT (Bruker AXS, 1997-2009)'
_computing_cell_refinement       'DENZO/SCALEPACK (Bruker AXS, 1997-2009)'
_computing_data_reduction        'DENZO/SCALEPACK (Bruker AXS, 1997-2009)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'XPMA (Zsolnai, Huttner, 1994)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²+3.6049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8130
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1360
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.07951(4) 0.70894(4) 0.24062(3) 0.02372(14) Uani 1 1 d . . . . .
S2 S 0.08430(4) 0.73367(4) 0.07472(3) 0.02833(15) Uani 1 1 d . . . . .
F1 F 0.09522(11) 0.65970(10) 0.34963(7) 0.0438(4) Uani 1 1 d . . . . .
F2 F -0.00042(10) 0.75633(12) 0.33487(8) 0.0505(5) Uani 1 1 d . . . . .
F3 F 0.13241(10) 0.79147(10) 0.33439(7) 0.0445(4) Uani 1 1 d . . . . .
F4 F 0.02144(11) 0.66140(13) -0.01764(8) 0.0618(5) Uani 1 1 d . . . . .
F5 F 0.15507(12) 0.63889(15) -0.00601(9) 0.0726(7) Uani 1 1 d . . . . .
F6 F 0.11101(15) 0.76196(17) -0.03626(9) 0.0859(8) Uani 1 1 d . . . . .
O1 O 0.16809(9) 0.67404(10) 0.23413(7) 0.0239(4) Uani 1 1 d . . . . .
O2 O 0.01713(10) 0.64273(10) 0.23403(8) 0.0295(4) Uani 1 1 d . . . . .
O3 O 0.06699(10) 0.78992(10) 0.21264(8) 0.0302(4) Uani 1 1 d . . . . .
O4 O 0.16888(10) 0.77607(10) 0.08416(8) 0.0280(4) Uani 1 1 d . . . . .
O5 O 0.07309(11) 0.65684(11) 0.10761(8) 0.0349(4) Uani 1 1 d . . . . .
O6 O 0.01781(12) 0.79563(12) 0.07278(9) 0.0425(5) Uani 1 1 d . . . . .
N1 N 0.29136(12) 0.77729(12) 0.22775(9) 0.0223(4) Uani 1 1 d . . . . .
N2 N 0.29234(12) 0.83191(12) 0.13492(9) 0.0243(4) Uani 1 1 d . . . . .
N3 N 0.36118(12) 0.90927(12) 0.20983(9) 0.0261(4) Uani 1 1 d . . . . .
N4 N 0.29643(12) 0.62294(12) 0.18529(9) 0.0225(4) Uani 1 1 d . . . . .
N5 N 0.29685(12) 0.67786(12) 0.09258(9) 0.0241(4) Uani 1 1 d . . . . .
N6 N 0.38024(12) 0.55465(12) 0.11366(9) 0.0266(4) Uani 1 1 d . . . . .
B1 B 0.24438(16) 0.70595(16) 0.19439(12) 0.0223(5) Uani 1 1 d . . . . .
B2 B 0.24489(17) 0.74702(16) 0.12486(12) 0.0233(5) Uani 1 1 d . . . . .
C1 C 0.31596(14) 0.84114(14) 0.19109(11) 0.0233(5) Uani 1 1 d . . . . .
C2 C 0.32507(15) 0.77525(15) 0.28717(11) 0.0274(5) Uani 1 1 d . . . . .
H2A H 0.381333 0.749394 0.287002 0.033 Uiso 1 1 calc R U . . .
H2B H 0.288379 0.740437 0.311866 0.033 Uiso 1 1 calc R U . . .
C3 C 0.33031(16) 0.86613(16) 0.31166(12) 0.0320(6) Uani 1 1 d . . . . .
H3A H 0.273634 0.890690 0.314476 0.038 Uiso 1 1 calc R U . . .
H3B H 0.355030 0.864898 0.350658 0.038 Uiso 1 1 calc R U . . .
C4 C 0.38503(16) 0.92065(16) 0.27134(12) 0.0317(6) Uani 1 1 d . . . . .
H4A H 0.378895 0.980814 0.281957 0.038 Uiso 1 1 calc R U . . .
H4B H 0.444386 0.904913 0.276438 0.038 Uiso 1 1 calc R U . . .
C5 C 0.39033(16) 0.97634(15) 0.16881(12) 0.0331(6) Uani 1 1 d . . . . .
H5A H 0.446618 0.995849 0.180316 0.040 Uiso 1 1 calc R U . . .
H5B H 0.351938 1.025205 0.170703 0.040 Uiso 1 1 calc R U . . .
C6 C 0.39342(16) 0.94279(16) 0.10681(12) 0.0328(6) Uani 1 1 d . . . . .
H6A H 0.439606 0.901689 0.102878 0.039 Uiso 1 1 calc R U . . .
H6B H 0.403804 0.989958 0.079850 0.039 Uiso 1 1 calc R U . . .
C7 C 0.30966(16) 0.89978(15) 0.09201(12) 0.0308(6) Uani 1 1 d . . . . .
H7A H 0.264092 0.941964 0.092681 0.037 Uiso 1 1 calc R U . . .
H7B H 0.312462 0.875233 0.052924 0.037 Uiso 1 1 calc R U . . .
C8 C 0.32600(14) 0.61739(14) 0.13026(11) 0.0228(5) Uani 1 1 d . . . . .
C9 C 0.32444(15) 0.56460(14) 0.23207(11) 0.0258(5) Uani 1 1 d . . . . .
H9A H 0.276730 0.552060 0.257747 0.031 Uiso 1 1 calc R U . . .
H9B H 0.368250 0.592603 0.255249 0.031 Uiso 1 1 calc R U . . .
C10 C 0.35907(15) 0.48149(15) 0.20738(11) 0.0277(5) Uani 1 1 d . . . . .
H10A H 0.312486 0.446451 0.192810 0.033 Uiso 1 1 calc R U . . .
H10B H 0.387873 0.449545 0.238107 0.033 Uiso 1 1 calc R U . . .
C11 C 0.42078(15) 0.50009(15) 0.15809(12) 0.0295(5) Uani 1 1 d . . . . .
H11A H 0.470754 0.528945 0.173598 0.035 Uiso 1 1 calc R U . . .
H11B H 0.438993 0.446425 0.140283 0.035 Uiso 1 1 calc R U . . .
C12 C 0.41801(17) 0.55302(17) 0.05472(12) 0.0349(6) Uani 1 1 d . . . . .
H12A H 0.425963 0.493770 0.042434 0.042 Uiso 1 1 calc R U . . .
H12B H 0.473490 0.580516 0.055769 0.042 Uiso 1 1 calc R U . . .
C13 C 0.36177(17) 0.59901(17) 0.01088(12) 0.0342(6) Uani 1 1 d . . . . .
H13A H 0.310552 0.565619 0.003806 0.041 Uiso 1 1 calc R U . . .
H13B H 0.391729 0.605664 -0.026072 0.041 Uiso 1 1 calc R U . . .
C14 C 0.33841(16) 0.68673(16) 0.03539(11) 0.0305(6) Uani 1 1 d . . . . .
H14A H 0.389472 0.721405 0.039491 0.037 Uiso 1 1 calc R U . . .
H14B H 0.300351 0.715898 0.008382 0.037 Uiso 1 1 calc R U . . .
C15 C 0.07723(16) 0.73045(16) 0.31928(12) 0.0332(6) Uani 1 1 d . . . . .
C16 C 0.09416(19) 0.6973(2) -0.00059(14) 0.0470(8) Uani 1 1 d . . . . .
Cl1 Cl -0.12463(5) 0.48329(5) 0.12460(4) 0.0512(2) Uani 1 1 d . . . . .
Cl2 Cl -0.21975(6) 0.63065(6) 0.08086(4) 0.0638(3) Uani 1 1 d . . . . .
C17 C -0.1183(2) 0.5893(2) 0.09732(16) 0.0569(9) Uani 1 1 d . . . . .
H17A H -0.091041 0.625856 0.126301 0.068 Uiso 1 1 calc R U . . .
H17B H -0.083446 0.589870 0.062173 0.068 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4237(17) . ?
S1 O2 1.4277(17) . ?
S1 O1 1.4994(16) . ?
S1 C15 1.824(3) . ?
S2 O6 1.4202(19) . ?
S2 O5 1.4201(18) . ?
S2 O4 1.4972(17) . ?
S2 C16 1.813(3) . ?
F1 C15 1.329(3) . ?
F2 C15 1.332(3) . ?
F3 C15 1.329(3) . ?
F4 C16 1.328(3) . ?
F5 C16 1.324(4) . ?
F6 C16 1.319(4) . ?
O1 B1 1.581(3) . ?
O4 B2 1.577(3) . ?
N1 C1 1.353(3) . ?
N1 C2 1.454(3) . ?
N1 B1 1.533(3) . ?
N2 C1 1.340(3) . ?
N2 C7 1.463(3) . ?
N2 B2 1.531(3) . ?
N3 C1 1.344(3) . ?
N3 C4 1.462(3) . ?
N3 C5 1.473(3) . ?
N4 C8 1.340(3) . ?
N4 C9 1.467(3) . ?
N4 B1 1.540(3) . ?
N5 C8 1.352(3) . ?
N5 C14 1.464(3) . ?
N5 B2 1.536(3) . ?
N6 C8 1.348(3) . ?
N6 C11 1.466(3) . ?
N6 C12 1.468(3) . ?
B1 B2 1.708(4) . ?
C2 C3 1.520(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.516(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.507(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.512(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.509(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.511(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.513(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.517(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
Cl1 C17 1.763(3) . ?
Cl2 C17 1.757(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 119.64(10) . . ?
O3 S1 O1 113.76(10) . . ?
O2 S1 O1 111.41(10) . . ?
O3 S1 C15 106.01(11) . . ?
O2 S1 C15 102.82(11) . . ?
O1 S1 C15 100.45(11) . . ?
O6 S2 O5 119.65(12) . . ?
O6 S2 O4 110.97(11) . . ?
O5 S2 O4 113.80(10) . . ?
O6 S2 C16 104.13(14) . . ?
O5 S2 C16 104.39(14) . . ?
O4 S2 C16 101.38(12) . . ?
S1 O1 B1 130.20(14) . . ?
S2 O4 B2 129.00(15) . . ?
C1 N1 C2 119.16(19) . . ?
C1 N1 B1 111.14(19) . . ?
C2 N1 B1 128.41(19) . . ?
C1 N2 C7 120.7(2) . . ?
C1 N2 B2 111.68(19) . . ?
C7 N2 B2 127.6(2) . . ?
C1 N3 C4 122.4(2) . . ?
C1 N3 C5 121.3(2) . . ?
C4 N3 C5 116.34(19) . . ?
C8 N4 C9 122.47(19) . . ?
C8 N4 B1 111.32(19) . . ?
C9 N4 B1 125.32(19) . . ?
C8 N5 C14 118.7(2) . . ?
C8 N5 B2 111.2(2) . . ?
C14 N5 B2 126.66(19) . . ?
C8 N6 C11 119.9(2) . . ?
C8 N6 C12 121.6(2) . . ?
C11 N6 C12 116.54(19) . . ?
N1 B1 N4 114.63(19) . . ?
N1 B1 O1 107.86(19) . . ?
N4 B1 O1 102.50(17) . . ?
N1 B1 B2 100.84(18) . . ?
N4 B1 B2 100.68(18) . . ?
O1 B1 B2 130.69(19) . . ?
N2 B2 N5 114.5(2) . . ?
N2 B2 O4 102.10(17) . . ?
N5 B2 O4 108.65(19) . . ?
N2 B2 B1 100.65(19) . . ?
N5 B2 B1 100.70(18) . . ?
O4 B2 B1 130.5(2) . . ?
N2 C1 N3 122.3(2) . . ?
N2 C1 N1 115.63(19) . . ?
N3 C1 N1 122.1(2) . . ?
N1 C2 C3 110.0(2) . . ?
N1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C2 109.1(2) . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N3 C4 C3 111.63(19) . . ?
N3 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
N3 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
N3 C5 C6 111.14(19) . . ?
N3 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
N3 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 109.5(2) . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C6 109.3(2) . . ?
N2 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
N4 C8 N6 121.9(2) . . ?
N4 C8 N5 115.6(2) . . ?
N6 C8 N5 122.5(2) . . ?
N4 C9 C10 111.4(2) . . ?
N4 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N4 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 110.15(19) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N6 C11 C10 110.24(19) . . ?
N6 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
N6 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N6 C12 C13 111.1(2) . . ?
N6 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
N6 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 108.8(2) . . ?
C12 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
C12 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
N5 C14 C13 110.5(2) . . ?
N5 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
F1 C15 F3 108.4(2) . . ?
F1 C15 F2 107.8(2) . . ?
F3 C15 F2 108.2(2) . . ?
F1 C15 S1 110.86(17) . . ?
F3 C15 S1 111.87(18) . . ?
F2 C15 S1 109.60(19) . . ?
F6 C16 F5 108.6(3) . . ?
F6 C16 F4 108.2(3) . . ?
F5 C16 F4 107.8(3) . . ?
F6 C16 S2 111.3(2) . . ?
F5 C16 S2 111.3(2) . . ?
F4 C16 S2 109.5(2) . . ?
Cl2 C17 Cl1 111.42(18) . . ?
Cl2 C17 H17A 109.3 . . ?
Cl1 C17 H17A 109.3 . . ?
Cl2 C17 H17B 109.3 . . ?
Cl1 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 O1 B1 -9.7(2) . . . . ?
O2 S1 O1 B1 129.17(19) . . . . ?
C15 S1 O1 B1 -122.5(2) . . . . ?
O6 S2 O4 B2 138.4(2) . . . . ?
O5 S2 O4 B2 0.0(2) . . . . ?
C16 S2 O4 B2 -111.5(2) . . . . ?
C1 N1 B1 N4 105.7(2) . . . . ?
C2 N1 B1 N4 -61.1(3) . . . . ?
C1 N1 B1 O1 -140.90(18) . . . . ?
C2 N1 B1 O1 52.4(3) . . . . ?
C1 N1 B1 B2 -1.5(2) . . . . ?
C2 N1 B1 B2 -168.2(2) . . . . ?
C8 N4 B1 N1 -103.2(2) . . . . ?
C9 N4 B1 N1 66.2(3) . . . . ?
C8 N4 B1 O1 140.28(18) . . . . ?
C9 N4 B1 O1 -50.3(3) . . . . ?
C8 N4 B1 B2 4.1(2) . . . . ?
C9 N4 B1 B2 173.48(19) . . . . ?
S1 O1 B1 N1 85.1(2) . . . . ?
S1 O1 B1 N4 -153.59(16) . . . . ?
S1 O1 B1 B2 -37.4(3) . . . . ?
C1 N2 B2 N5 -105.9(2) . . . . ?
C7 N2 B2 N5 76.5(3) . . . . ?
C1 N2 B2 O4 136.85(19) . . . . ?
C7 N2 B2 O4 -40.8(3) . . . . ?
C1 N2 B2 B1 1.1(2) . . . . ?
C7 N2 B2 B1 -176.5(2) . . . . ?
C8 N5 B2 N2 102.8(2) . . . . ?
C14 N5 B2 N2 -55.6(3) . . . . ?
C8 N5 B2 O4 -143.76(18) . . . . ?
C14 N5 B2 O4 57.8(3) . . . . ?
C8 N5 B2 B1 -4.2(2) . . . . ?
C14 N5 B2 B1 -162.6(2) . . . . ?
S2 O4 B2 N2 -156.97(16) . . . . ?
S2 O4 B2 N5 81.6(2) . . . . ?
S2 O4 B2 B1 -41.4(3) . . . . ?
N1 B1 B2 N2 0.2(2) . . . . ?
N4 B1 B2 N2 -117.67(18) . . . . ?
O1 B1 B2 N2 125.4(2) . . . . ?
N1 B1 B2 N5 117.98(18) . . . . ?
N4 B1 B2 N5 0.1(2) . . . . ?
O1 B1 B2 N5 -116.8(2) . . . . ?
N1 B1 B2 O4 -115.9(2) . . . . ?
N4 B1 B2 O4 126.2(2) . . . . ?
O1 B1 B2 O4 9.2(4) . . . . ?
C7 N2 C1 N3 -4.6(3) . . . . ?
B2 N2 C1 N3 177.6(2) . . . . ?
C7 N2 C1 N1 175.4(2) . . . . ?
B2 N2 C1 N1 -2.4(3) . . . . ?
C4 N3 C1 N2 178.3(2) . . . . ?
C5 N3 C1 N2 -2.4(3) . . . . ?
C4 N3 C1 N1 -1.8(3) . . . . ?
C5 N3 C1 N1 177.5(2) . . . . ?
C2 N1 C1 N2 170.64(19) . . . . ?
B1 N1 C1 N2 2.5(3) . . . . ?
C2 N1 C1 N3 -9.3(3) . . . . ?
B1 N1 C1 N3 -177.4(2) . . . . ?
C1 N1 C2 C3 39.3(3) . . . . ?
B1 N1 C2 C3 -155.0(2) . . . . ?
N1 C2 C3 C4 -57.1(3) . . . . ?
C1 N3 C4 C3 -18.7(3) . . . . ?
C5 N3 C4 C3 162.0(2) . . . . ?
C2 C3 C4 N3 47.0(3) . . . . ?
C1 N3 C5 C6 -21.7(3) . . . . ?
C4 N3 C5 C6 157.6(2) . . . . ?
N3 C5 C6 C7 50.3(3) . . . . ?
C1 N2 C7 C6 34.5(3) . . . . ?
B2 N2 C7 C6 -148.1(2) . . . . ?
C5 C6 C7 N2 -56.3(3) . . . . ?
C9 N4 C8 N6 3.6(3) . . . . ?
B1 N4 C8 N6 173.3(2) . . . . ?
C9 N4 C8 N5 -177.40(19) . . . . ?
B1 N4 C8 N5 -7.7(3) . . . . ?
C11 N6 C8 N4 -11.4(3) . . . . ?
C12 N6 C8 N4 -174.8(2) . . . . ?
C11 N6 C8 N5 169.7(2) . . . . ?
C12 N6 C8 N5 6.2(3) . . . . ?
C14 N5 C8 N4 168.1(2) . . . . ?
B2 N5 C8 N4 7.7(3) . . . . ?
C14 N5 C8 N6 -12.9(3) . . . . ?
B2 N5 C8 N6 -173.2(2) . . . . ?
C8 N4 C9 C10 -22.7(3) . . . . ?
B1 N4 C9 C10 169.1(2) . . . . ?
N4 C9 C10 C11 47.3(3) . . . . ?
C8 N6 C11 C10 37.3(3) . . . . ?
C12 N6 C11 C10 -158.5(2) . . . . ?
C9 C10 C11 N6 -54.4(3) . . . . ?
C8 N6 C12 C13 -26.1(3) . . . . ?
C11 N6 C12 C13 169.9(2) . . . . ?
N6 C12 C13 C14 50.2(3) . . . . ?
C8 N5 C14 C13 38.8(3) . . . . ?
B2 N5 C14 C13 -164.2(2) . . . . ?
C12 C13 C14 N5 -56.8(3) . . . . ?
O3 S1 C15 F1 -174.99(16) . . . . ?
O2 S1 C15 F1 58.64(19) . . . . ?
O1 S1 C15 F1 -56.36(19) . . . . ?
O3 S1 C15 F3 -53.8(2) . . . . ?
O2 S1 C15 F3 179.82(17) . . . . ?
O1 S1 C15 F3 64.82(19) . . . . ?
O3 S1 C15 F2 66.2(2) . . . . ?
O2 S1 C15 F2 -60.2(2) . . . . ?
O1 S1 C15 F2 -175.19(17) . . . . ?
O6 S2 C16 F6 58.2(2) . . . . ?
O5 S2 C16 F6 -175.6(2) . . . . ?
O4 S2 C16 F6 -57.1(2) . . . . ?
O6 S2 C16 F5 179.5(2) . . . . ?
O5 S2 C16 F5 -54.2(2) . . . . ?
O4 S2 C16 F5 64.2(2) . . . . ?
O6 S2 C16 F4 -61.4(3) . . . . ?
O5 S2 C16 F4 64.8(3) . . . . ?
O4 S2 C16 F4 -176.7(2) . . . . ?

_refine_diff_density_max         0.637
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_jh324a_sq
_database_code_depnum_ccdc_archive 'CCDC 1585620'
_audit_update_record             
;
2017-12-19 deposited with the CCDC.
2017-12-26 downloaded from the CCDC.
;
#============================================================================== 
_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H38 B2 Cl4 N6'
_chemical_formula_weight         670.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.7100(17)
_cell_length_b                   12.033(2)
_cell_length_c                   19.074(4)
_cell_angle_alpha                93.53(3)
_cell_angle_beta                 99.26(3)
_cell_angle_gamma                110.89(3)
_cell_volume                     1827.9(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120
_cell_measurement_reflns_used    2584
_cell_measurement_theta_min      1.1
_cell_measurement_theta_max      30.0

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             700
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.354
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'NONIUS KAPPA CCD'
_diffrn_measurement_method       'O-Scan    '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15250
_diffrn_reflns_av_unetI/netI     0.0899
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.003
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8279
_reflns_number_gt                4634
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'COLLECT (Bruker AXS, 1997-2009)'
_computing_cell_refinement       'DENZO/SCALEPACK (Bruker AXS, 1997-2009)'
_computing_data_reduction        'DENZO/SCALEPACK (Bruker AXS, 1997-2009)'
_computing_structure_solution    'SHELXS-2016 (sheldrick 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'XPMA (Zsolnai, Huttner, 1994)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²+0.5256P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8279
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1563
_refine_ls_wR_factor_gt          0.1340
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.32248(13) 0.41253(8) 0.03222(5) 0.0595(3) Uani 1 1 d . . . . .
Cl2 Cl 0.21260(10) 0.15395(8) 0.00392(5) 0.0520(2) Uani 1 1 d . . . . .
Cl3 Cl 0.69673(12) 0.24077(11) 0.31164(7) 0.0863(4) Uani 1 1 d . . . . .
Cl4 Cl 0.54328(15) 0.30654(12) 0.42502(6) 0.0874(4) Uani 1 1 d . . . . .
N1 N 0.0496(3) 0.37528(19) 0.18917(12) 0.0254(5) Uani 1 1 d . . . . .
N2 N -0.0663(3) 0.17313(19) 0.17922(12) 0.0247(5) Uani 1 1 d . . . . .
N3 N -0.2201(3) 0.27601(19) 0.11766(12) 0.0275(5) Uani 1 1 d . . . . .
N4 N 0.1720(3) 0.3778(2) 0.32245(12) 0.0281(5) Uani 1 1 d . . . . .
N5 N 0.0691(3) 0.1750(2) 0.31056(12) 0.0285(5) Uani 1 1 d . . . . .
N6 N 0.0921(3) 0.2815(2) 0.42201(13) 0.0340(6) Uani 1 1 d . . . . .
B1 B 0.1871(4) 0.3520(3) 0.24295(17) 0.0266(7) Uani 1 1 d . . . . .
B2 B 0.1006(4) 0.1937(3) 0.23266(17) 0.0251(7) Uani 1 1 d . . . . .
C1 C -0.0828(3) 0.2750(2) 0.16210(14) 0.0239(6) Uani 1 1 d . . . . .
C2 C 0.0441(3) 0.4927(2) 0.17861(16) 0.0313(7) Uani 1 1 d . . . . .
H2A H 0.156258 0.549151 0.178742 0.038 Uiso 1 1 calc R U . . .
H2B H 0.003609 0.521417 0.217757 0.038 Uiso 1 1 calc R U . . .
C3 C -0.0699(3) 0.4864(3) 0.10820(16) 0.0327(7) Uani 1 1 d . . . . .
H3A H -0.081327 0.563131 0.104060 0.039 Uiso 1 1 calc R U . . .
H3B H -0.022190 0.467997 0.068528 0.039 Uiso 1 1 calc R U . . .
C4 C -0.2391(3) 0.3902(2) 0.10573(17) 0.0323(7) Uani 1 1 d . . . . .
H4A H -0.291655 0.413008 0.142333 0.039 Uiso 1 1 calc R U . . .
H4B H -0.310466 0.381267 0.059458 0.039 Uiso 1 1 calc R U . . .
C5 C -0.3713(3) 0.1663(2) 0.09924(16) 0.0317(7) Uani 1 1 d . . . . .
H5A H -0.440729 0.170957 0.055200 0.038 Uiso 1 1 calc R U . . .
H5B H -0.435593 0.158274 0.136972 0.038 Uiso 1 1 calc R U . . .
C6 C -0.3221(3) 0.0582(2) 0.08987(16) 0.0315(7) Uani 1 1 d . . . . .
H6A H -0.421478 -0.014669 0.081404 0.038 Uiso 1 1 calc R U . . .
H6B H -0.268898 0.061866 0.048680 0.038 Uiso 1 1 calc R U . . .
C7 C -0.2025(3) 0.0561(2) 0.15634(16) 0.0309(7) Uani 1 1 d . . . . .
H7A H -0.263650 0.033600 0.194757 0.037 Uiso 1 1 calc R U . . .
H7B H -0.155549 -0.003862 0.146641 0.037 Uiso 1 1 calc R U . . .
C8 C 0.1104(3) 0.2778(3) 0.35321(15) 0.0272(6) Uani 1 1 d . . . . .
C9 C 0.2357(4) 0.4945(3) 0.36604(16) 0.0351(7) Uani 1 1 d . . . . .
H9A H 0.231793 0.555696 0.335738 0.042 Uiso 1 1 calc R U . . .
H9B H 0.351581 0.513848 0.388901 0.042 Uiso 1 1 calc R U . . .
C10 C 0.1324(4) 0.4934(3) 0.42229(17) 0.0415(8) Uani 1 1 d . . . . .
H10A H 0.179928 0.569774 0.452875 0.050 Uiso 1 1 calc R U . . .
H10B H 0.019067 0.482046 0.399481 0.050 Uiso 1 1 calc R U . . .
C11 C 0.1290(4) 0.3940(3) 0.46667(18) 0.0461(8) Uani 1 1 d . . . . .
H11A H 0.236728 0.415814 0.498560 0.055 Uiso 1 1 calc R U . . .
H11B H 0.044494 0.383363 0.495861 0.055 Uiso 1 1 calc R U . . .
C12 C 0.0324(4) 0.1722(3) 0.45565(17) 0.0424(8) Uani 1 1 d . . . . .
H12A H -0.085214 0.151498 0.457170 0.051 Uiso 1 1 calc R U . . .
H12B H 0.094136 0.186131 0.504513 0.051 Uiso 1 1 calc R U . . .
C13 C 0.0548(4) 0.0689(3) 0.41455(17) 0.0445(8) Uani 1 1 d . . . . .
H13A H 0.172820 0.081215 0.421793 0.053 Uiso 1 1 calc R U . . .
H13B H -0.003706 -0.005583 0.432059 0.053 Uiso 1 1 calc R U . . .
C14 C -0.0136(4) 0.0613(3) 0.33612(16) 0.0372(7) Uani 1 1 d . . . . .
H14A H 0.005115 -0.002455 0.309510 0.045 Uiso 1 1 calc R U . . .
H14B H -0.133344 0.042927 0.328491 0.045 Uiso 1 1 calc R U . . .
C15 C 0.3698(4) 0.4358(2) 0.23603(15) 0.0287(6) Uani 1 1 d . . . . .
C16 C 0.5124(3) 0.5047(3) 0.23954(15) 0.0299(7) Uani 1 1 d . . . . .
C17 C 0.6804(3) 0.5914(2) 0.24946(16) 0.0282(6) Uani 1 1 d . . . . .
C18 C 0.7370(3) 0.6594(2) 0.19551(16) 0.0300(7) Uani 1 1 d . . . . .
H18 H 0.666406 0.645967 0.151156 0.036 Uiso 1 1 calc R U . . .
C19 C 0.8967(4) 0.7465(3) 0.20716(17) 0.0348(7) Uani 1 1 d . . . . .
H19 H 0.932615 0.791380 0.170815 0.042 Uiso 1 1 calc R U . . .
C20 C 1.0030(4) 0.7670(3) 0.27288(18) 0.0371(8) Uani 1 1 d . . . . .
H20 H 1.109881 0.826054 0.280732 0.044 Uiso 1 1 calc R U . . .
C21 C 0.9508(4) 0.6999(3) 0.32695(17) 0.0363(7) Uani 1 1 d . . . . .
H21 H 1.022788 0.713403 0.370940 0.044 Uiso 1 1 calc R U . . .
C22 C 0.7896(3) 0.6118(3) 0.31530(16) 0.0328(7) Uani 1 1 d . . . . .
H22 H 0.754837 0.566535 0.351614 0.039 Uiso 1 1 calc R U . . .
C23 C 0.1799(3) 0.1033(2) 0.20652(15) 0.0269(6) Uani 1 1 d . . . . .
C24 C 0.2345(3) 0.0293(2) 0.18674(15) 0.0276(6) Uani 1 1 d . . . . .
C25 C 0.2844(3) -0.0661(2) 0.16225(15) 0.0255(6) Uani 1 1 d . . . . .
C26 C 0.3994(3) -0.1000(3) 0.20642(16) 0.0311(7) Uani 1 1 d . . . . .
H26 H 0.450991 -0.057366 0.251629 0.037 Uiso 1 1 calc R U . . .
C27 C 0.4374(4) -0.1969(3) 0.18328(17) 0.0356(7) Uani 1 1 d . . . . .
H27 H 0.513222 -0.219577 0.213318 0.043 Uiso 1 1 calc R U . . .
C28 C 0.3637(4) -0.2595(3) 0.11623(17) 0.0363(7) Uani 1 1 d . . . . .
H28 H 0.390208 -0.324117 0.100868 0.044 Uiso 1 1 calc R U . . .
C29 C 0.2496(4) -0.2263(3) 0.07139(17) 0.0337(7) Uani 1 1 d . . . . .
H29 H 0.199474 -0.268736 0.026031 0.040 Uiso 1 1 calc R U . . .
C30 C 0.2108(3) -0.1302(2) 0.09432(16) 0.0312(7) Uani 1 1 d . . . . .
H30 H 0.134748 -0.108075 0.064082 0.037 Uiso 1 1 calc R U . . .
C31 C 0.2414(5) 0.2766(3) 0.06688(19) 0.0467(9) Uani 1 1 d . . . . .
H31A H 0.134874 0.268458 0.079692 0.056 Uiso 1 1 calc R U . . .
H31B H 0.317702 0.276625 0.109957 0.056 Uiso 1 1 calc R U . . .
C32 C 0.5131(4) 0.2499(3) 0.33424(18) 0.0478(9) Uani 1 1 d . . . . .
H32A H 0.425187 0.170705 0.324662 0.057 Uiso 1 1 calc R U . . .
H32B H 0.476514 0.301527 0.304235 0.057 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C31 1.753(3) . ?
Cl2 C31 1.762(3) . ?
Cl3 C32 1.760(3) . ?
Cl4 C32 1.764(4) . ?
N1 C1 1.338(3) . ?
N1 C2 1.456(3) . ?
N1 B1 1.564(4) . ?
N2 C1 1.337(3) . ?
N2 C7 1.465(3) . ?
N2 B2 1.565(4) . ?
N3 C1 1.355(3) . ?
N3 C5 1.467(3) . ?
N3 C4 1.469(3) . ?
N4 C8 1.345(3) . ?
N4 C9 1.458(4) . ?
N4 B1 1.565(4) . ?
N5 C8 1.336(4) . ?
N5 C14 1.456(4) . ?
N5 B2 1.569(4) . ?
N6 C8 1.347(4) . ?
N6 C11 1.457(4) . ?
N6 C12 1.461(4) . ?
B1 C15 1.583(4) . ?
B1 B2 1.765(4) . ?
B2 C23 1.579(4) . ?
C2 C3 1.517(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.505(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.517(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.513(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.505(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.502(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.516(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.503(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.210(4) . ?
C16 C17 1.437(4) . ?
C17 C18 1.397(4) . ?
C17 C22 1.398(4) . ?
C18 C19 1.384(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.397(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.216(4) . ?
C24 C25 1.442(4) . ?
C25 C26 1.394(4) . ?
C25 C30 1.394(4) . ?
C26 C27 1.387(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.374(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.389(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.381(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 120.8(2) . . ?
C1 N1 B1 112.9(2) . . ?
C2 N1 B1 125.2(2) . . ?
C1 N2 C7 121.9(2) . . ?
C1 N2 B2 113.4(2) . . ?
C7 N2 B2 124.3(2) . . ?
C1 N3 C5 119.7(2) . . ?
C1 N3 C4 120.2(2) . . ?
C5 N3 C4 117.5(2) . . ?
C8 N4 C9 119.4(2) . . ?
C8 N4 B1 113.4(2) . . ?
C9 N4 B1 126.7(2) . . ?
C8 N5 C14 119.7(2) . . ?
C8 N5 B2 113.3(2) . . ?
C14 N5 B2 126.6(2) . . ?
C8 N6 C11 122.0(3) . . ?
C8 N6 C12 121.6(3) . . ?
C11 N6 C12 116.4(2) . . ?
N1 B1 N4 111.6(2) . . ?
N1 B1 C15 111.7(2) . . ?
N4 B1 C15 106.6(2) . . ?
N1 B1 B2 99.3(2) . . ?
N4 B1 B2 99.0(2) . . ?
C15 B1 B2 127.7(2) . . ?
N2 B2 N5 111.2(2) . . ?
N2 B2 C23 109.1(2) . . ?
N5 B2 C23 109.6(2) . . ?
N2 B2 B1 98.8(2) . . ?
N5 B2 B1 99.1(2) . . ?
C23 B2 B1 128.0(2) . . ?
N2 C1 N1 115.2(2) . . ?
N2 C1 N3 122.3(2) . . ?
N1 C1 N3 122.4(2) . . ?
N1 C2 C3 110.7(2) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 109.0(2) . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N3 C4 C3 109.8(2) . . ?
N3 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
N3 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N3 C5 C6 109.7(2) . . ?
N3 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
N3 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C7 C6 C5 110.0(2) . . ?
C7 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C6 111.6(2) . . ?
N2 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N5 C8 N4 115.1(2) . . ?
N5 C8 N6 122.7(3) . . ?
N4 C8 N6 122.2(3) . . ?
N4 C9 C10 110.3(2) . . ?
N4 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N4 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 110.0(3) . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N6 C11 C10 111.6(3) . . ?
N6 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
N6 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N6 C12 C13 110.9(3) . . ?
N6 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
N6 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 109.6(3) . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N5 C14 C13 109.7(3) . . ?
N5 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
N5 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 B1 172.0(3) . . ?
C15 C16 C17 175.0(3) . . ?
C18 C17 C22 118.5(2) . . ?
C18 C17 C16 121.7(3) . . ?
C22 C17 C16 119.8(3) . . ?
C19 C18 C17 120.9(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 119.8(3) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C17 120.5(3) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?
C24 C23 B2 177.0(3) . . ?
C23 C24 C25 175.0(3) . . ?
C26 C25 C30 118.7(3) . . ?
C26 C25 C24 121.4(3) . . ?
C30 C25 C24 119.8(3) . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C28 C27 C26 120.4(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C25 120.8(3) . . ?
C29 C30 H30 119.6 . . ?
C25 C30 H30 119.6 . . ?
Cl1 C31 Cl2 111.03(18) . . ?
Cl1 C31 H31A 109.4 . . ?
Cl2 C31 H31A 109.4 . . ?
Cl1 C31 H31B 109.4 . . ?
Cl2 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
Cl3 C32 Cl4 112.27(18) . . ?
Cl3 C32 H32A 109.2 . . ?
Cl4 C32 H32A 109.2 . . ?
Cl3 C32 H32B 109.2 . . ?
Cl4 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 B1 N4 -97.7(3) . . . . ?
C2 N1 B1 N4 70.6(3) . . . . ?
C1 N1 B1 C15 143.0(2) . . . . ?
C2 N1 B1 C15 -48.6(4) . . . . ?
C1 N1 B1 B2 5.9(3) . . . . ?
C2 N1 B1 B2 174.3(2) . . . . ?
C8 N4 B1 N1 106.5(3) . . . . ?
C9 N4 B1 N1 -81.6(3) . . . . ?
C8 N4 B1 C15 -131.3(2) . . . . ?
C9 N4 B1 C15 40.6(3) . . . . ?
C8 N4 B1 B2 2.7(3) . . . . ?
C9 N4 B1 B2 174.6(2) . . . . ?
C1 N2 B2 N5 103.1(3) . . . . ?
C7 N2 B2 N5 -69.6(3) . . . . ?
C1 N2 B2 C23 -135.8(2) . . . . ?
C7 N2 B2 C23 51.5(3) . . . . ?
C1 N2 B2 B1 -0.3(3) . . . . ?
C7 N2 B2 B1 -173.0(2) . . . . ?
C8 N5 B2 N2 -101.2(3) . . . . ?
C14 N5 B2 N2 72.0(3) . . . . ?
C8 N5 B2 C23 138.1(2) . . . . ?
C14 N5 B2 C23 -48.8(3) . . . . ?
C8 N5 B2 B1 2.1(3) . . . . ?
C14 N5 B2 B1 175.2(2) . . . . ?
N1 B1 B2 N2 -3.1(2) . . . . ?
N4 B1 B2 N2 110.8(2) . . . . ?
C15 B1 B2 N2 -129.9(3) . . . . ?
N1 B1 B2 N5 -116.4(2) . . . . ?
N4 B1 B2 N5 -2.6(2) . . . . ?
C15 B1 B2 N5 116.7(3) . . . . ?
N1 B1 B2 C23 119.7(3) . . . . ?
N4 B1 B2 C23 -126.4(3) . . . . ?
C15 B1 B2 C23 -7.1(5) . . . . ?
C7 N2 C1 N1 177.4(2) . . . . ?
B2 N2 C1 N1 4.5(3) . . . . ?
C7 N2 C1 N3 -5.8(4) . . . . ?
B2 N2 C1 N3 -178.7(2) . . . . ?
C2 N1 C1 N2 -175.9(2) . . . . ?
B1 N1 C1 N2 -7.0(3) . . . . ?
C2 N1 C1 N3 7.2(4) . . . . ?
B1 N1 C1 N3 176.1(2) . . . . ?
C5 N3 C1 N2 13.3(4) . . . . ?
C4 N3 C1 N2 174.4(2) . . . . ?
C5 N3 C1 N1 -170.1(2) . . . . ?
C4 N3 C1 N1 -9.0(4) . . . . ?
C1 N1 C2 C3 -30.4(4) . . . . ?
B1 N1 C2 C3 162.1(2) . . . . ?
N1 C2 C3 C4 53.8(3) . . . . ?
C1 N3 C4 C3 33.8(4) . . . . ?
C5 N3 C4 C3 -164.7(2) . . . . ?
C2 C3 C4 N3 -55.1(3) . . . . ?
C1 N3 C5 C6 -38.3(3) . . . . ?
C4 N3 C5 C6 160.2(2) . . . . ?
N3 C5 C6 C7 54.9(3) . . . . ?
C1 N2 C7 C6 24.3(4) . . . . ?
B2 N2 C7 C6 -163.5(2) . . . . ?
C5 C6 C7 N2 -48.3(3) . . . . ?
C14 N5 C8 N4 -174.2(2) . . . . ?
B2 N5 C8 N4 -0.5(3) . . . . ?
C14 N5 C8 N6 5.9(4) . . . . ?
B2 N5 C8 N6 179.6(2) . . . . ?
C9 N4 C8 N5 -174.2(2) . . . . ?
B1 N4 C8 N5 -1.7(3) . . . . ?
C9 N4 C8 N6 5.7(4) . . . . ?
B1 N4 C8 N6 178.2(2) . . . . ?
C11 N6 C8 N5 -176.5(3) . . . . ?
C12 N6 C8 N5 2.9(4) . . . . ?
C11 N6 C8 N4 3.6(4) . . . . ?
C12 N6 C8 N4 -177.1(2) . . . . ?
C8 N4 C9 C10 -35.7(3) . . . . ?
B1 N4 C9 C10 152.9(3) . . . . ?
N4 C9 C10 C11 55.8(3) . . . . ?
C8 N6 C11 C10 18.5(4) . . . . ?
C12 N6 C11 C10 -160.9(3) . . . . ?
C9 C10 C11 N6 -47.3(4) . . . . ?
C8 N6 C12 C13 19.8(4) . . . . ?
C11 N6 C12 C13 -160.8(3) . . . . ?
N6 C12 C13 C14 -48.9(4) . . . . ?
C8 N5 C14 C13 -36.3(4) . . . . ?
B2 N5 C14 C13 150.9(3) . . . . ?
C12 C13 C14 N5 56.9(3) . . . . ?
C22 C17 C18 C19 -1.0(4) . . . . ?
C16 C17 C18 C19 176.9(3) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C18 C19 C20 C21 0.6(4) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C20 C21 C22 C17 -0.3(4) . . . . ?
C18 C17 C22 C21 1.0(4) . . . . ?
C16 C17 C22 C21 -176.9(3) . . . . ?
C30 C25 C26 C27 -1.0(4) . . . . ?
C24 C25 C26 C27 175.9(3) . . . . ?
C25 C26 C27 C28 0.9(4) . . . . ?
C26 C27 C28 C29 -0.4(4) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
C28 C29 C30 C25 -0.3(4) . . . . ?
C26 C25 C30 C29 0.7(4) . . . . ?
C24 C25 C30 C29 -176.2(2) . . . . ?

_refine_diff_density_max         0.697
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.062

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 1.000 0.500 222 85 ' CH2Cl2 '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?



