# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_LBA003_cmpd4HBF4
_database_code_depnum_ccdc_archive 'CCDC 1955376'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2019-09-23 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

#============================================================================== 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H24 N3, B F4, C H2 Cl2'
_chemical_formula_sum            'C33 H26 B Cl2 F4 N3'
_chemical_formula_weight         622.28

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

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

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

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

_cell_length_a                   10.2647(3)
_cell_length_b                   11.6265(4)
_cell_length_c                   13.2263(4)
_cell_angle_alpha                74.145(2)
_cell_angle_beta                 82.775(2)
_cell_angle_gamma                72.328(2)
_cell_volume                     1445.18(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    7881
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      27.76

_exptl_crystal_description       'rectangular plate'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.280
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7054
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25693
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.602
_diffrn_reflns_theta_max         27.811
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6732
_reflns_number_gt                4100
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0807P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6732
_refine_ls_number_parameters     396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1513
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 0.98200(7) 0.93869(7) 0.88967(6) 0.0514(2) Uani 1 1 d . . . . .
Cl2 Cl 0.77458(7) 0.92632(7) 0.76521(6) 0.0566(2) Uani 1 1 d . . . . .
B1 B 0.8815(3) 0.5523(3) 0.8230(2) 0.0286(6) Uani 1 1 d . . . . .
F1 F 0.84692(13) 0.57866(13) 0.91991(10) 0.0376(4) Uani 1 1 d . . . . .
F2 F 0.77321(13) 0.62870(13) 0.75424(10) 0.0357(4) Uani 1 1 d . . . . .
F3 F 1.00020(13) 0.58152(13) 0.77940(10) 0.0392(4) Uani 1 1 d . . . . .
F4 F 0.89129(15) 0.43008(13) 0.82883(12) 0.0523(5) Uani 1 1 d . . . . .
N1 N 0.58325(16) 0.41658(16) 0.65617(13) 0.0213(4) Uani 1 1 d . . . . .
N2 N 0.52739(19) 0.55458(17) 0.77610(14) 0.0217(4) Uani 1 1 d . . . . .
H2N H 0.589(2) 0.591(2) 0.7590(19) 0.040(8) Uiso 1 1 d . . . . .
N3 N 0.72771(17) 0.55447(16) 0.57964(14) 0.0208(4) Uani 1 1 d . . . . .
H3N H 0.733(2) 0.586(2) 0.6347(18) 0.029(6) Uiso 1 1 d . . . . .
C1 C 0.4343(2) 0.57033(19) 0.85701(16) 0.0213(5) Uani 1 1 d . . . . .
C2 C 0.3638(2) 0.4794(2) 0.87412(16) 0.0240(5) Uani 1 1 d . . . . .
H2 H 0.2919 0.4701 0.9256 0.029 Uiso 1 1 calc R U . . .
C3 C 0.4156(2) 0.40665(19) 0.80458(16) 0.0210(5) Uani 1 1 d . . . . .
C4 C 0.5206(2) 0.45478(19) 0.73905(16) 0.0206(5) Uani 1 1 d . . . . .
C5 C 0.4157(2) 0.66480(19) 0.91405(16) 0.0221(5) Uani 1 1 d . . . . .
C6 C 0.3082(2) 0.6795(2) 0.99013(17) 0.0295(5) Uani 1 1 d . . . . .
H6 H 0.2498 0.6268 1.0041 0.035 Uiso 1 1 calc R U . . .
C7 C 0.2861(2) 0.7691(2) 1.04484(17) 0.0324(6) Uani 1 1 d . . . . .
H7 H 0.2120 0.7787 1.0956 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3713(2) 0.8456(2) 1.02632(18) 0.0305(6) Uani 1 1 d . . . . .
H8 H 0.3559 0.9074 1.0643 0.037 Uiso 1 1 calc R U . . .
C9 C 0.4791(2) 0.8316(2) 0.95228(17) 0.0287(5) Uani 1 1 d . . . . .
H9 H 0.5382 0.8836 0.9402 0.034 Uiso 1 1 calc R U . . .
C10 C 0.5016(2) 0.7432(2) 0.89593(17) 0.0264(5) Uani 1 1 d . . . . .
H10 H 0.5753 0.7351 0.8447 0.032 Uiso 1 1 calc R U . . .
C11 C 0.3714(2) 0.2998(2) 0.79889(16) 0.0238(5) Uani 1 1 d . . . . .
C12 C 0.4562(2) 0.2020(2) 0.75826(17) 0.0264(5) Uani 1 1 d . . . . .
H12 H 0.5457 0.2045 0.7308 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4110(2) 0.1018(2) 0.75767(18) 0.0301(5) Uani 1 1 d . . . . .
H13 H 0.4693 0.0366 0.7289 0.036 Uiso 1 1 calc R U . . .
C14 C 0.2818(2) 0.0953(2) 0.79846(19) 0.0337(6) Uani 1 1 d . . . . .
H14 H 0.2513 0.0260 0.7979 0.040 Uiso 1 1 calc R U . . .
C15 C 0.1978(2) 0.1905(2) 0.83993(18) 0.0323(6) Uani 1 1 d . . . . .
H15 H 0.1091 0.1864 0.8683 0.039 Uiso 1 1 calc R U . . .
C16 C 0.2410(2) 0.2918(2) 0.84074(17) 0.0265(5) Uani 1 1 d . . . . .
H16 H 0.1820 0.3564 0.8698 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6682(2) 0.4606(2) 0.58317(16) 0.0212(5) Uani 1 1 d . . . . .
C18 C 0.8026(2) 0.57659(19) 0.48758(16) 0.0213(5) Uani 1 1 d . . . . .
C19 C 0.7911(2) 0.49671(19) 0.42917(16) 0.0220(5) Uani 1 1 d . . . . .
H19 H 0.8319 0.4939 0.3610 0.026 Uiso 1 1 calc R U . . .
C20 C 0.7113(2) 0.42285(19) 0.48611(16) 0.0209(5) Uani 1 1 d . . . . .
C21 C 0.8762(2) 0.6710(2) 0.46039(16) 0.0216(5) Uani 1 1 d . . . . .
C22 C 0.8540(2) 0.7619(2) 0.51677(18) 0.0287(5) Uani 1 1 d . . . . .
H22 H 0.7903 0.7623 0.5755 0.034 Uiso 1 1 calc R U . . .
C23 C 0.9243(2) 0.8507(2) 0.48739(19) 0.0351(6) Uani 1 1 d . . . . .
H23 H 0.9084 0.9122 0.5257 0.042 Uiso 1 1 calc R U . . .
C24 C 1.0182(2) 0.8508(2) 0.40196(18) 0.0338(6) Uani 1 1 d . . . . .
H24 H 1.0667 0.9120 0.3822 0.041 Uiso 1 1 calc R U . . .
C25 C 1.0409(2) 0.7620(2) 0.34609(18) 0.0302(6) Uani 1 1 d . . . . .
H25 H 1.1052 0.7620 0.2878 0.036 Uiso 1 1 calc R U . . .
C26 C 0.9704(2) 0.6727(2) 0.37447(16) 0.0255(5) Uani 1 1 d . . . . .
H26 H 0.9864 0.6120 0.3352 0.031 Uiso 1 1 calc R U . . .
C27 C 0.6797(2) 0.32369(19) 0.45352(16) 0.0218(5) Uani 1 1 d . . . . .
C28 C 0.7644(2) 0.2725(2) 0.37545(17) 0.0280(5) Uani 1 1 d . . . . .
H28 H 0.8386 0.3044 0.3433 0.034 Uiso 1 1 calc R U . . .
C29 C 0.7409(2) 0.1767(2) 0.34507(18) 0.0330(6) Uani 1 1 d . . . . .
H29 H 0.7991 0.1429 0.2922 0.040 Uiso 1 1 calc R U . . .
C30 C 0.6331(2) 0.1290(2) 0.39094(19) 0.0339(6) Uani 1 1 d . . . . .
H30 H 0.6182 0.0620 0.3703 0.041 Uiso 1 1 calc R U . . .
C31 C 0.5478(2) 0.1790(2) 0.46642(18) 0.0310(6) Uani 1 1 d . . . . .
H31 H 0.4737 0.1465 0.4977 0.037 Uiso 1 1 calc R U . . .
C32 C 0.5693(2) 0.2766(2) 0.49734(17) 0.0256(5) Uani 1 1 d . . . . .
H32 H 0.5086 0.3116 0.5485 0.031 Uiso 1 1 calc R U . . .
C33 C 0.9009(3) 0.8421(3) 0.8570(2) 0.0574(8) Uani 1 1 d . . . . .
H33A H 0.8583 0.7987 0.9216 0.063 Uiso 1 1 calc R U . . .
H33B H 0.9701 0.7781 0.8274 0.063 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 C33 1.750(3) . ?
Cl2 C33 1.758(3) . ?
B1 F4 1.375(3) . ?
B1 F1 1.377(3) . ?
B1 F3 1.379(3) . ?
B1 F2 1.437(3) . ?
N1 C4 1.314(3) . ?
N1 C17 1.321(3) . ?
N2 C1 1.355(3) . ?
N2 C4 1.400(3) . ?
N2 H2N 0.84(2) . ?
N3 C18 1.361(3) . ?
N3 C17 1.391(3) . ?
N3 H3N 0.92(2) . ?
C1 C2 1.409(3) . ?
C1 C5 1.450(3) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.446(3) . ?
C3 C11 1.469(3) . ?
C5 C6 1.400(3) . ?
C5 C10 1.407(3) . ?
C6 C7 1.374(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.398(3) . ?
C11 C16 1.403(3) . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C20 1.444(3) . ?
C18 C19 1.398(3) . ?
C18 C21 1.458(3) . ?
C19 C20 1.376(3) . ?
C19 H19 0.9500 . ?
C20 C27 1.467(3) . ?
C21 C26 1.397(3) . ?
C21 C22 1.402(3) . ?
C22 C23 1.378(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C32 1.400(3) . ?
C27 C28 1.404(3) . ?
C28 C29 1.376(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.385(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.375(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.390(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F4 B1 F1 111.3(2) . . ?
F4 B1 F3 111.1(2) . . ?
F1 B1 F3 111.6(2) . . ?
F4 B1 F2 107.3(2) . . ?
F1 B1 F2 107.72(19) . . ?
F3 B1 F2 107.55(19) . . ?
C4 N1 C17 131.02(19) . . ?
C1 N2 C4 110.11(18) . . ?
C1 N2 H2N 124.0(17) . . ?
C4 N2 H2N 125.0(17) . . ?
C18 N3 C17 109.92(18) . . ?
C18 N3 H3N 122.2(14) . . ?
C17 N3 H3N 126.6(14) . . ?
N2 C1 C2 107.81(19) . . ?
N2 C1 C5 124.20(19) . . ?
C2 C1 C5 127.99(19) . . ?
C3 C2 C1 109.04(19) . . ?
C3 C2 H2 125.5 . . ?
C1 C2 H2 125.5 . . ?
C2 C3 C4 107.27(19) . . ?
C2 C3 C11 125.6(2) . . ?
C4 C3 C11 127.08(19) . . ?
N1 C4 N2 129.39(19) . . ?
N1 C4 C3 124.5(2) . . ?
N2 C4 C3 105.76(17) . . ?
C6 C5 C10 118.3(2) . . ?
C6 C5 C1 119.1(2) . . ?
C10 C5 C1 122.59(19) . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 119.8(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C5 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
C12 C11 C16 118.2(2) . . ?
C12 C11 C3 122.9(2) . . ?
C16 C11 C3 118.9(2) . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.8(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N1 C17 N3 128.63(19) . . ?
N1 C17 C20 125.02(19) . . ?
N3 C17 C20 106.27(18) . . ?
N3 C18 C19 107.83(18) . . ?
N3 C18 C21 122.80(19) . . ?
C19 C18 C21 129.35(19) . . ?
C20 C19 C18 109.20(19) . . ?
C20 C19 H19 125.4 . . ?
C18 C19 H19 125.4 . . ?
C19 C20 C17 106.75(18) . . ?
C19 C20 C27 125.73(19) . . ?
C17 C20 C27 127.50(19) . . ?
C26 C21 C22 118.7(2) . . ?
C26 C21 C18 119.2(2) . . ?
C22 C21 C18 122.16(19) . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.4(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 119.9(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.3(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.5(2) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C32 C27 C28 118.1(2) . . ?
C32 C27 C20 123.02(19) . . ?
C28 C27 C20 118.84(19) . . ?
C29 C28 C27 120.6(2) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 120.6(2) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C29 119.7(2) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 120.5(2) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C31 C32 C27 120.4(2) . . ?
C31 C32 H32 119.8 . . ?
C27 C32 H32 119.8 . . ?
Cl1 C33 Cl2 112.03(16) . . ?
Cl1 C33 H33A 109.2 . . ?
Cl2 C33 H33A 109.2 . . ?
Cl1 C33 H33B 109.2 . . ?
Cl2 C33 H33B 109.2 . . ?
H33A C33 H33B 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
C4 N2 C1 C2 -0.1(2) . . . . ?
C4 N2 C1 C5 179.24(18) . . . . ?
N2 C1 C2 C3 1.0(2) . . . . ?
C5 C1 C2 C3 -178.35(19) . . . . ?
C1 C2 C3 C4 -1.4(2) . . . . ?
C1 C2 C3 C11 178.56(18) . . . . ?
C17 N1 C4 N2 -1.1(4) . . . . ?
C17 N1 C4 C3 171.3(2) . . . . ?
C1 N2 C4 N1 172.8(2) . . . . ?
C1 N2 C4 C3 -0.7(2) . . . . ?
C2 C3 C4 N1 -172.60(19) . . . . ?
C11 C3 C4 N1 7.4(3) . . . . ?
C2 C3 C4 N2 1.3(2) . . . . ?
C11 C3 C4 N2 -178.67(19) . . . . ?
N2 C1 C5 C6 174.4(2) . . . . ?
C2 C1 C5 C6 -6.4(3) . . . . ?
N2 C1 C5 C10 -5.5(3) . . . . ?
C2 C1 C5 C10 173.8(2) . . . . ?
C10 C5 C6 C7 0.8(3) . . . . ?
C1 C5 C6 C7 -179.1(2) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C5 -0.7(3) . . . . ?
C6 C5 C10 C9 0.0(3) . . . . ?
C1 C5 C10 C9 179.86(19) . . . . ?
C2 C3 C11 C12 -154.6(2) . . . . ?
C4 C3 C11 C12 25.4(3) . . . . ?
C2 C3 C11 C16 22.0(3) . . . . ?
C4 C3 C11 C16 -158.0(2) . . . . ?
C16 C11 C12 C13 1.3(3) . . . . ?
C3 C11 C12 C13 178.00(19) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C12 C11 C16 C15 -1.0(3) . . . . ?
C3 C11 C16 C15 -177.83(19) . . . . ?
C4 N1 C17 N3 7.6(4) . . . . ?
C4 N1 C17 C20 -168.6(2) . . . . ?
C18 N3 C17 N1 -176.4(2) . . . . ?
C18 N3 C17 C20 0.4(2) . . . . ?
C17 N3 C18 C19 0.6(2) . . . . ?
C17 N3 C18 C21 179.31(18) . . . . ?
N3 C18 C19 C20 -1.3(2) . . . . ?
C21 C18 C19 C20 -180.0(2) . . . . ?
C18 C19 C20 C17 1.5(2) . . . . ?
C18 C19 C20 C27 -177.40(19) . . . . ?
N1 C17 C20 C19 175.7(2) . . . . ?
N3 C17 C20 C19 -1.2(2) . . . . ?
N1 C17 C20 C27 -5.4(3) . . . . ?
N3 C17 C20 C27 177.74(19) . . . . ?
N3 C18 C21 C26 168.22(19) . . . . ?
C19 C18 C21 C26 -13.3(3) . . . . ?
N3 C18 C21 C22 -12.7(3) . . . . ?
C19 C18 C21 C22 165.7(2) . . . . ?
C26 C21 C22 C23 0.0(3) . . . . ?
C18 C21 C22 C23 -179.0(2) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C21 -0.4(3) . . . . ?
C22 C21 C26 C25 0.3(3) . . . . ?
C18 C21 C26 C25 179.37(19) . . . . ?
C19 C20 C27 C32 -160.8(2) . . . . ?
C17 C20 C27 C32 20.5(3) . . . . ?
C19 C20 C27 C28 19.7(3) . . . . ?
C17 C20 C27 C28 -159.0(2) . . . . ?
C32 C27 C28 C29 -1.6(3) . . . . ?
C20 C27 C28 C29 177.9(2) . . . . ?
C27 C28 C29 C30 0.1(3) . . . . ?
C28 C29 C30 C31 0.9(4) . . . . ?
C29 C30 C31 C32 -0.3(4) . . . . ?
C30 C31 C32 C27 -1.3(3) . . . . ?
C28 C27 C32 C31 2.2(3) . . . . ?
C20 C27 C32 C31 -177.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N F2 0.84(2) 2.06(2) 2.862(2) 161(2) .
N3 H3N F2 0.92(2) 1.90(2) 2.811(2) 170(2) .

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.072

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_LBA002_cmpd4HBr
_database_code_depnum_ccdc_archive 'CCDC 1955377'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2019-09-23 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C32 H24 N3), C H2 Cl2, 2(Br)'
_chemical_formula_sum            'C65 H50 Br2 Cl2 N6'
_chemical_formula_weight         1145.83

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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.429(2)
_cell_length_b                   10.505(3)
_cell_length_c                   13.733(3)
_cell_angle_alpha                72.898(3)
_cell_angle_beta                 88.384(3)
_cell_angle_gamma                80.368(3)
_cell_volume                     1281.5(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    2256
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      23.25

_exptl_crystal_description       'thin rectangular needle'
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             586
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.736
_shelx_estimated_absorpt_T_min   0.671
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6418
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13954
_diffrn_reflns_av_unetI/netI     0.1518
_diffrn_reflns_av_R_equivalents  0.1076
_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       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.552
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5211
_reflns_number_gt                3080
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0289P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5211
_refine_ls_number_parameters     360
_refine_ls_number_restraints     297
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.936
_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
Br1 Br 0.25496(5) 0.54510(5) 0.25727(4) 0.02330(15) Uani 1 1 d . . . . .
C33 C 0.0674(11) 0.5236(10) 0.0402(7) 0.037(3) Uani 0.5 1 d D U P A -1
H33A H 0.0462 0.5673 0.0949 0.044 Uiso 0.5 1 calc R U P A -1
H33B H 0.1668 0.5332 0.0176 0.044 Uiso 0.5 1 calc R U P A -1
Cl1 Cl 0.0550(13) 0.3508(8) 0.0882(7) 0.0381(16) Uani 0.5 1 d D U P A -1
Cl2 Cl -0.0538(13) 0.6046(8) -0.0629(8) 0.052(2) Uani 0.5 1 d D U P A -1
N1 N 0.3811(4) 0.2154(4) 0.5416(3) 0.0182(9) Uani 1 1 d . U . . .
N2 N 0.1498(4) 0.3236(4) 0.4540(3) 0.0171(9) Uani 1 1 d D U . . .
H2N H 0.177(5) 0.377(4) 0.394(2) 0.07(2) Uiso 1 1 d D . . . .
N3 N 0.4421(4) 0.2495(4) 0.3615(3) 0.0186(9) Uani 1 1 d D U . . .
H3N H 0.371(4) 0.321(3) 0.333(3) 0.049(17) Uiso 1 1 d D . . . .
C1 C 0.2412(5) 0.2577(4) 0.5390(3) 0.0187(10) Uani 1 1 d . U . . .
C2 C 0.0116(5) 0.3397(4) 0.4851(3) 0.0177(10) Uani 1 1 d . U . . .
C3 C 0.0109(5) 0.2824(4) 0.5916(3) 0.0196(11) Uani 1 1 d . U . . .
H3 H -0.0724 0.2779 0.6323 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1506(5) 0.2337(4) 0.6270(3) 0.0195(10) Uani 1 1 d . U . . .
C5 C -0.1109(5) 0.4044(4) 0.4152(3) 0.0174(10) Uani 1 1 d . U . . .
C6 C -0.2478(4) 0.4339(4) 0.4550(3) 0.0203(11) Uani 1 1 d . U . . .
H6 H -0.2599 0.4135 0.5265 0.024 Uiso 1 1 calc R U . . .
C7 C -0.3645(5) 0.4927(4) 0.3889(3) 0.0224(11) Uani 1 1 d . U . . .
H7 H -0.4569 0.5122 0.4156 0.027 Uiso 1 1 calc R U . . .
C8 C -0.3483(5) 0.5236(5) 0.2841(3) 0.0246(11) Uani 1 1 d . U . . .
H8 H -0.4291 0.5641 0.2393 0.030 Uiso 1 1 calc R U . . .
C9 C -0.2131(5) 0.4947(5) 0.2454(3) 0.0241(11) Uani 1 1 d . U . . .
H9 H -0.2012 0.5161 0.1738 0.029 Uiso 1 1 calc R U . . .
C10 C -0.0966(5) 0.4356(4) 0.3097(3) 0.0220(11) Uani 1 1 d . U . . .
H10 H -0.0049 0.4156 0.2822 0.026 Uiso 1 1 calc R U . . .
C11 C 0.1946(5) 0.1746(4) 0.7352(3) 0.0188(10) Uani 1 1 d . U . . .
C12 C 0.3320(5) 0.1069(5) 0.7674(4) 0.0279(12) Uani 1 1 d . U . . .
H12 H 0.4016 0.0925 0.7187 0.033 Uiso 1 1 calc R U . . .
C13 C 0.3686(5) 0.0601(5) 0.8707(4) 0.0388(14) Uani 1 1 d . U . . .
H13 H 0.4634 0.0149 0.8921 0.047 Uiso 1 1 calc R U . . .
C14 C 0.2677(5) 0.0791(5) 0.9424(4) 0.0335(13) Uani 1 1 d . U . . .
H14 H 0.2937 0.0484 1.0128 0.040 Uiso 1 1 calc R U . . .
C15 C 0.1304(5) 0.1422(5) 0.9118(4) 0.0299(12) Uani 1 1 d . U . . .
H15 H 0.0604 0.1527 0.9612 0.036 Uiso 1 1 calc R U . . .
C16 C 0.0933(5) 0.1906(5) 0.8098(3) 0.0260(12) Uani 1 1 d . U . . .
H16 H -0.0019 0.2355 0.7894 0.031 Uiso 1 1 calc R U . . .
C17 C 0.4715(5) 0.2106(4) 0.4664(3) 0.0176(10) Uani 1 1 d . U . . .
C18 C 0.5624(5) 0.2118(4) 0.3131(3) 0.0206(11) Uani 1 1 d . U . . .
C19 C 0.6701(5) 0.1436(4) 0.3871(3) 0.0213(11) Uani 1 1 d . U . . .
H19 H 0.7639 0.1035 0.3739 0.026 Uiso 1 1 calc R U . . .
C20 C 0.6189(5) 0.1437(4) 0.4818(3) 0.0203(10) Uani 1 1 d . U . . .
C21 C 0.5665(5) 0.2427(5) 0.2024(3) 0.0237(11) Uani 1 1 d . U . . .
C22 C 0.4405(5) 0.2778(5) 0.1432(4) 0.0327(13) Uani 1 1 d . U . . .
H22 H 0.3499 0.2821 0.1752 0.039 Uiso 1 1 calc R U . . .
C23 C 0.4458(6) 0.3065(5) 0.0388(4) 0.0381(14) Uani 1 1 d . U . . .
H23 H 0.3591 0.3290 -0.0007 0.046 Uiso 1 1 calc R U . . .
C24 C 0.5767(6) 0.3024(5) -0.0086(4) 0.0412(14) Uani 1 1 d . U . . .
H24 H 0.5805 0.3236 -0.0807 0.049 Uiso 1 1 calc R U . . .
C25 C 0.7005(6) 0.2678(7) 0.0486(4) 0.0554(18) Uani 1 1 d . U . . .
H25 H 0.7905 0.2645 0.0158 0.067 Uiso 1 1 calc R U . . .
C26 C 0.6976(5) 0.2370(6) 0.1545(4) 0.0424(15) Uani 1 1 d . U . . .
H26 H 0.7849 0.2122 0.1934 0.051 Uiso 1 1 calc R U . . .
C27 C 0.6990(4) 0.0870(4) 0.5794(3) 0.0199(10) Uani 1 1 d . U . . .
C28 C 0.8124(5) -0.0203(5) 0.5899(4) 0.0292(12) Uani 1 1 d . U . . .
H28 H 0.8356 -0.0566 0.5346 0.035 Uiso 1 1 calc R U . . .
C29 C 0.8914(5) -0.0744(5) 0.6805(4) 0.0327(13) Uani 1 1 d . U . . .
H29 H 0.9674 -0.1486 0.6875 0.039 Uiso 1 1 calc R U . . .
C30 C 0.8600(5) -0.0206(5) 0.7607(4) 0.0333(13) Uani 1 1 d . U . . .
H30 H 0.9143 -0.0579 0.8227 0.040 Uiso 1 1 calc R U . . .
C31 C 0.7497(5) 0.0873(5) 0.7508(4) 0.0255(12) Uani 1 1 d . U . . .
H31 H 0.7290 0.1247 0.8057 0.031 Uiso 1 1 calc R U . . .
C32 C 0.6692(5) 0.1411(5) 0.6608(3) 0.0212(11) Uani 1 1 d . U . . .
H32 H 0.5934 0.2152 0.6545 0.025 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
C33 Cl2 1.758(12) . ?
C33 Cl1 1.762(10) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
N1 C1 1.318(5) . ?
N1 C17 1.327(5) . ?
N2 C2 1.358(5) . ?
N2 C1 1.403(5) . ?
N2 H2N 0.905(19) . ?
N3 C18 1.359(5) . ?
N3 C17 1.400(5) . ?
N3 H3N 0.915(19) . ?
C1 C4 1.445(6) . ?
C2 C3 1.408(6) . ?
C2 C5 1.462(6) . ?
C3 C4 1.378(6) . ?
C3 H3 0.9500 . ?
C4 C11 1.474(6) . ?
C5 C10 1.395(6) . ?
C5 C6 1.410(6) . ?
C6 C7 1.383(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.370(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.385(6) . ?
C11 C16 1.408(6) . ?
C12 C13 1.390(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.368(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C20 1.440(6) . ?
C18 C19 1.402(6) . ?
C18 C21 1.458(6) . ?
C19 C20 1.375(6) . ?
C19 H19 0.9500 . ?
C20 C27 1.469(6) . ?
C21 C26 1.385(6) . ?
C21 C22 1.394(6) . ?
C22 C23 1.377(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.361(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(7) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.395(6) . ?
C27 C32 1.398(6) . ?
C28 C29 1.387(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.383(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.381(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.385(6) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 C33 Cl1 111.0(9) . . ?
Cl2 C33 H33A 109.4 . . ?
Cl1 C33 H33A 109.4 . . ?
Cl2 C33 H33B 109.4 . . ?
Cl1 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C1 N1 C17 130.3(4) . . ?
C2 N2 C1 109.2(4) . . ?
C2 N2 H2N 121(3) . . ?
C1 N2 H2N 125(3) . . ?
C18 N3 C17 109.2(4) . . ?
C18 N3 H3N 125(3) . . ?
C17 N3 H3N 120(3) . . ?
N1 C1 N2 128.7(4) . . ?
N1 C1 C4 124.6(4) . . ?
N2 C1 C4 106.6(4) . . ?
N2 C2 C3 108.5(4) . . ?
N2 C2 C5 123.2(4) . . ?
C3 C2 C5 128.3(4) . . ?
C4 C3 C2 108.8(4) . . ?
C4 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
C3 C4 C1 106.8(4) . . ?
C3 C4 C11 124.9(4) . . ?
C1 C4 C11 128.2(4) . . ?
C10 C5 C6 119.0(4) . . ?
C10 C5 C2 121.7(4) . . ?
C6 C5 C2 119.3(4) . . ?
C7 C6 C5 119.4(4) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 120.9(4) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 119.4(4) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C5 120.8(4) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
C12 C11 C16 118.2(4) . . ?
C12 C11 C4 123.2(4) . . ?
C16 C11 C4 118.5(4) . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.9(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.3(5) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.9(4) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N1 C17 N3 128.7(4) . . ?
N1 C17 C20 123.9(4) . . ?
N3 C17 C20 106.9(4) . . ?
N3 C18 C19 108.1(4) . . ?
N3 C18 C21 121.9(4) . . ?
C19 C18 C21 129.9(4) . . ?
C20 C19 C18 109.3(4) . . ?
C20 C19 H19 125.3 . . ?
C18 C19 H19 125.3 . . ?
C19 C20 C17 106.5(4) . . ?
C19 C20 C27 126.7(4) . . ?
C17 C20 C27 126.8(4) . . ?
C26 C21 C22 118.8(5) . . ?
C26 C21 C18 119.9(4) . . ?
C22 C21 C18 121.3(4) . . ?
C23 C22 C21 120.8(5) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.1(5) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 119.6(5) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 121.2(5) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C21 C26 C25 119.5(5) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C28 C27 C32 118.8(4) . . ?
C28 C27 C20 119.1(4) . . ?
C32 C27 C20 122.0(4) . . ?
C29 C28 C27 120.4(5) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 120.2(5) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C31 C30 C29 120.1(5) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 120.1(5) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C32 C27 120.4(4) . . ?
C31 C32 H32 119.8 . . ?
C27 C32 H32 119.8 . . ?

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
C17 N1 C1 N2 -7.6(8) . . . . ?
C17 N1 C1 C4 167.4(4) . . . . ?
C2 N2 C1 N1 175.3(4) . . . . ?
C2 N2 C1 C4 -0.4(5) . . . . ?
C1 N2 C2 C3 -0.8(5) . . . . ?
C1 N2 C2 C5 -179.6(4) . . . . ?
N2 C2 C3 C4 1.7(5) . . . . ?
C5 C2 C3 C4 -179.5(4) . . . . ?
C2 C3 C4 C1 -1.9(5) . . . . ?
C2 C3 C4 C11 175.7(4) . . . . ?
N1 C1 C4 C3 -174.5(4) . . . . ?
N2 C1 C4 C3 1.4(5) . . . . ?
N1 C1 C4 C11 8.0(8) . . . . ?
N2 C1 C4 C11 -176.1(4) . . . . ?
N2 C2 C5 C10 10.0(7) . . . . ?
C3 C2 C5 C10 -168.6(4) . . . . ?
N2 C2 C5 C6 -171.1(4) . . . . ?
C3 C2 C5 C6 10.3(7) . . . . ?
C10 C5 C6 C7 0.1(7) . . . . ?
C2 C5 C6 C7 -178.8(4) . . . . ?
C5 C6 C7 C8 -0.3(7) . . . . ?
C6 C7 C8 C9 0.1(7) . . . . ?
C7 C8 C9 C10 0.4(7) . . . . ?
C8 C9 C10 C5 -0.6(7) . . . . ?
C6 C5 C10 C9 0.4(7) . . . . ?
C2 C5 C10 C9 179.2(4) . . . . ?
C3 C4 C11 C12 169.1(5) . . . . ?
C1 C4 C11 C12 -13.8(7) . . . . ?
C3 C4 C11 C16 -12.7(7) . . . . ?
C1 C4 C11 C16 164.5(5) . . . . ?
C16 C11 C12 C13 -1.8(7) . . . . ?
C4 C11 C12 C13 176.4(5) . . . . ?
C11 C12 C13 C14 0.8(8) . . . . ?
C12 C13 C14 C15 1.1(8) . . . . ?
C13 C14 C15 C16 -2.0(8) . . . . ?
C14 C15 C16 C11 0.9(8) . . . . ?
C12 C11 C16 C15 1.0(7) . . . . ?
C4 C11 C16 C15 -177.4(4) . . . . ?
C1 N1 C17 N3 -0.2(8) . . . . ?
C1 N1 C17 C20 -170.7(4) . . . . ?
C18 N3 C17 N1 -172.5(4) . . . . ?
C18 N3 C17 C20 -0.7(5) . . . . ?
C17 N3 C18 C19 2.0(5) . . . . ?
C17 N3 C18 C21 -178.0(4) . . . . ?
N3 C18 C19 C20 -2.6(5) . . . . ?
C21 C18 C19 C20 177.4(5) . . . . ?
C18 C19 C20 C17 2.1(5) . . . . ?
C18 C19 C20 C27 -177.8(4) . . . . ?
N1 C17 C20 C19 171.4(4) . . . . ?
N3 C17 C20 C19 -0.9(5) . . . . ?
N1 C17 C20 C27 -8.7(7) . . . . ?
N3 C17 C20 C27 179.0(4) . . . . ?
N3 C18 C21 C26 162.2(5) . . . . ?
C19 C18 C21 C26 -17.7(8) . . . . ?
N3 C18 C21 C22 -18.0(7) . . . . ?
C19 C18 C21 C22 162.1(5) . . . . ?
C26 C21 C22 C23 0.0(8) . . . . ?
C18 C21 C22 C23 -179.8(5) . . . . ?
C21 C22 C23 C24 -0.9(8) . . . . ?
C22 C23 C24 C25 1.1(9) . . . . ?
C23 C24 C25 C26 -0.4(9) . . . . ?
C22 C21 C26 C25 0.7(8) . . . . ?
C18 C21 C26 C25 -179.4(5) . . . . ?
C24 C25 C26 C21 -0.6(9) . . . . ?
C19 C20 C27 C28 -27.4(7) . . . . ?
C17 C20 C27 C28 152.6(4) . . . . ?
C19 C20 C27 C32 149.7(5) . . . . ?
C17 C20 C27 C32 -30.2(7) . . . . ?
C32 C27 C28 C29 1.7(7) . . . . ?
C20 C27 C28 C29 178.9(4) . . . . ?
C27 C28 C29 C30 -1.2(7) . . . . ?
C28 C29 C30 C31 0.0(7) . . . . ?
C29 C30 C31 C32 0.7(7) . . . . ?
C30 C31 C32 C27 -0.1(7) . . . . ?
C28 C27 C32 C31 -1.1(6) . . . . ?
C20 C27 C32 C31 -178.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N Br1 0.905(19) 2.37(2) 3.259(4) 169(5) .
N3 H3N Br1 0.915(19) 2.37(2) 3.240(4) 160(4) .

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.106

####################################################################### 
# 
# 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_RD003_cmpd8
_database_code_depnum_ccdc_archive 'CCDC 1955380'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2019-09-23 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

#============================================================================== 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H28 B N3, C6 H6'
_chemical_formula_sum            'C46 H34 B N3'
_chemical_formula_weight         639.57

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

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

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

_cell_length_a                   10.9702(11)
_cell_length_b                   12.8749(13)
_cell_length_c                   13.9596(14)
_cell_angle_alpha                67.6470(10)
_cell_angle_beta                 67.7290(10)
_cell_angle_gamma                88.5480(10)
_cell_volume                     1671.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      28.84

_exptl_crystal_description       'rough cube'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7073
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20441
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.721
_diffrn_reflns_theta_max         28.886
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8073
_reflns_number_gt                6462
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+0.4769P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_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         8073
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.43225(10) 0.75874(8) 0.54626(8) 0.0226(2) Uani 1 1 d . . . . .
N2 N 0.39836(10) 0.94161(8) 0.43113(8) 0.0244(2) Uani 1 1 d . . . . .
N3 N 0.23905(10) 0.85427(8) 0.62515(8) 0.0230(2) Uani 1 1 d . . . . .
B1 B 0.29626(13) 0.73390(11) 0.65364(11) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.53105(12) 0.69352(10) 0.53618(10) 0.0236(2) Uani 1 1 d . . . . .
C2 C 0.63840(12) 0.74977(10) 0.42887(10) 0.0247(2) Uani 1 1 d . . . . .
C3 C 0.76215(13) 0.71894(11) 0.37830(11) 0.0290(3) Uani 1 1 d . . . . .
H3 H 0.7881 0.6497 0.4168 0.035 Uiso 1 1 calc R U . . .
C4 C 0.84513(13) 0.79192(12) 0.27108(11) 0.0324(3) Uani 1 1 d . . . . .
H4 H 0.9297 0.7728 0.2352 0.039 Uiso 1 1 calc R U . . .
C5 C 0.80690(13) 0.89445(12) 0.21362(11) 0.0321(3) Uani 1 1 d . . . . .
H5 H 0.8665 0.9432 0.1398 0.038 Uiso 1 1 calc R U . . .
C6 C 0.68506(13) 0.92586(11) 0.26190(10) 0.0284(3) Uani 1 1 d . . . . .
H6 H 0.6598 0.9949 0.2224 0.034 Uiso 1 1 calc R U . . .
C7 C 0.59971(12) 0.85232(10) 0.37134(10) 0.0241(2) Uani 1 1 d . . . . .
C8 C 0.47018(12) 0.85727(10) 0.44695(10) 0.0238(2) Uani 1 1 d . . . . .
C9 C 0.28795(12) 0.93965(10) 0.51456(10) 0.0237(2) Uani 1 1 d . . . . .
C10 C 0.19914(12) 1.02346(10) 0.51028(10) 0.0246(2) Uani 1 1 d . . . . .
C11 C 0.19878(13) 1.12398(10) 0.42363(11) 0.0289(3) Uani 1 1 d . . . . .
H11 H 0.2681 1.1497 0.3502 0.035 Uiso 1 1 calc R U . . .
C12 C 0.09396(14) 1.18467(11) 0.44852(12) 0.0316(3) Uani 1 1 d . . . . .
H12 H 0.0907 1.2526 0.3906 0.038 Uiso 1 1 calc R U . . .
C13 C -0.00757(14) 1.14834(11) 0.55707(12) 0.0328(3) Uani 1 1 d . . . . .
H13 H -0.0780 1.1922 0.5712 0.039 Uiso 1 1 calc R U . . .
C14 C -0.00738(13) 1.05017(11) 0.64387(11) 0.0300(3) Uani 1 1 d . . . . .
H14 H -0.0754 1.0264 0.7177 0.036 Uiso 1 1 calc R U . . .
C15 C 0.09696(12) 0.98673(10) 0.61898(10) 0.0254(2) Uani 1 1 d . . . . .
C16 C 0.12605(12) 0.88210(10) 0.68780(10) 0.0247(2) Uani 1 1 d . . . . .
C17 C 0.52843(12) 0.58180(10) 0.62264(10) 0.0239(2) Uani 1 1 d . . . . .
C18 C 0.44590(12) 0.48581(10) 0.64918(10) 0.0260(3) Uani 1 1 d . . . . .
H18 H 0.3878 0.4913 0.6119 0.031 Uiso 1 1 calc R U . . .
C19 C 0.44804(13) 0.38195(11) 0.72991(11) 0.0294(3) Uani 1 1 d . . . . .
H19 H 0.3927 0.3164 0.7467 0.035 Uiso 1 1 calc R U . . .
C20 C 0.53073(14) 0.37388(11) 0.78583(11) 0.0325(3) Uani 1 1 d . . . . .
H20 H 0.5293 0.3036 0.8434 0.039 Uiso 1 1 calc R U . . .
C21 C 0.61551(14) 0.46822(12) 0.75797(12) 0.0350(3) Uani 1 1 d . . . . .
H21 H 0.6735 0.4621 0.7954 0.042 Uiso 1 1 calc R U . . .
C22 C 0.61616(13) 0.57155(11) 0.67569(11) 0.0314(3) Uani 1 1 d . . . . .
H22 H 0.6764 0.6355 0.6553 0.038 Uiso 1 1 calc R U . . .
C23 C 0.04242(13) 0.81679(10) 0.80859(10) 0.0270(3) Uani 1 1 d . . . . .
C24 C -0.09235(14) 0.78388(12) 0.84088(12) 0.0345(3) Uani 1 1 d . . . . .
H24 H -0.1286 0.8030 0.7854 0.041 Uiso 1 1 calc R U . . .
C25 C -0.17381(15) 0.72295(12) 0.95444(13) 0.0410(3) Uani 1 1 d . . . . .
H25 H -0.2650 0.6992 0.9760 0.049 Uiso 1 1 calc R U . . .
C26 C -0.12245(15) 0.69717(12) 1.03549(12) 0.0401(3) Uani 1 1 d . . . . .
H26 H -0.1781 0.6553 1.1128 0.048 Uiso 1 1 calc R U . . .
C27 C 0.00977(15) 0.73217(11) 1.00453(11) 0.0360(3) Uani 1 1 d . . . . .
H27 H 0.0444 0.7153 1.0608 0.043 Uiso 1 1 calc R U . . .
C28 C 0.09245(14) 0.79184(10) 0.89175(10) 0.0295(3) Uani 1 1 d . . . . .
H28 H 0.1833 0.8157 0.8712 0.035 Uiso 1 1 calc R U . . .
C29 C 0.33761(12) 0.70318(10) 0.75970(10) 0.0233(2) Uani 1 1 d . . . . .
C30 C 0.29964(13) 0.59978(10) 0.85351(10) 0.0270(3) Uani 1 1 d . . . . .
H30 H 0.2416 0.5422 0.8592 0.032 Uiso 1 1 calc R U . . .
C31 C 0.34480(15) 0.57904(12) 0.93896(11) 0.0358(3) Uani 1 1 d . . . . .
H31 H 0.3165 0.5082 1.0023 0.043 Uiso 1 1 calc R U . . .
C32 C 0.43047(16) 0.66086(14) 0.93208(12) 0.0433(4) Uani 1 1 d . . . . .
H32 H 0.4613 0.6467 0.9904 0.052 Uiso 1 1 calc R U . . .
C33 C 0.47098(15) 0.76382(13) 0.83922(12) 0.0404(3) Uani 1 1 d . . . . .
H33 H 0.5300 0.8206 0.8337 0.049 Uiso 1 1 calc R U . . .
C34 C 0.42562(13) 0.78415(11) 0.75447(11) 0.0298(3) Uani 1 1 d . . . . .
H34 H 0.4550 0.8549 0.6911 0.036 Uiso 1 1 calc R U . . .
C35 C 0.19033(12) 0.64565(10) 0.65698(10) 0.0231(2) Uani 1 1 d . . . . .
C36 C 0.07512(12) 0.58724(10) 0.75358(11) 0.0266(3) Uani 1 1 d . . . . .
H36 H 0.0607 0.5961 0.8214 0.032 Uiso 1 1 calc R U . . .
C37 C -0.01870(13) 0.51687(11) 0.75336(12) 0.0328(3) Uani 1 1 d . . . . .
H37 H -0.0956 0.4786 0.8204 0.039 Uiso 1 1 calc R U . . .
C38 C -0.00019(15) 0.50247(12) 0.65560(13) 0.0370(3) Uani 1 1 d . . . . .
H38 H -0.0640 0.4543 0.6552 0.044 Uiso 1 1 calc R U . . .
C39 C 0.11184(15) 0.55877(12) 0.55890(12) 0.0352(3) Uani 1 1 d . . . . .
H39 H 0.1252 0.5493 0.4915 0.042 Uiso 1 1 calc R U . . .
C40 C 0.20542(13) 0.62928(10) 0.55930(11) 0.0280(3) Uani 1 1 d . . . . .
H40 H 0.2817 0.6675 0.4917 0.034 Uiso 1 1 calc R U . . .
C41 C 0.70633(18) -0.02044(14) 0.97327(14) 0.0475(4) Uani 1 1 d . . . . .
H41 H 0.7097 -0.0799 1.0381 0.057 Uiso 1 1 calc R U . . .
C42 C 0.76675(18) 0.08738(14) 0.93812(15) 0.0495(4) Uani 1 1 d . . . . .
H42 H 0.8113 0.1026 0.9789 0.059 Uiso 1 1 calc R U . . .
C43 C 0.76270(18) 0.17312(15) 0.84402(16) 0.0539(4) Uani 1 1 d . . . . .
H43 H 0.8035 0.2479 0.8201 0.065 Uiso 1 1 calc R U . . .
C44 C 0.69863(18) 0.15006(16) 0.78385(14) 0.0526(4) Uani 1 1 d . . . . .
H44 H 0.6970 0.2090 0.7180 0.063 Uiso 1 1 calc R U . . .
C45 C 0.63787(18) 0.04259(16) 0.81934(14) 0.0505(4) Uani 1 1 d . . . . .
H45 H 0.5939 0.0268 0.7784 0.061 Uiso 1 1 calc R U . . .
C46 C 0.64101(19) -0.04233(15) 0.91468(15) 0.0525(4) Uani 1 1 d . . . . .
H46 H 0.5978 -0.1166 0.9402 0.063 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 1.3519(15) . ?
N1 C8 1.3986(15) . ?
N1 B1 1.5935(16) . ?
N2 C9 1.3168(16) . ?
N2 C8 1.3246(16) . ?
N3 C16 1.3506(15) . ?
N3 C9 1.4109(15) . ?
N3 B1 1.6201(16) . ?
B1 C29 1.6152(18) . ?
B1 C35 1.6214(18) . ?
C1 C2 1.4270(16) . ?
C1 C17 1.4771(16) . ?
C2 C3 1.3994(18) . ?
C2 C7 1.4114(17) . ?
C3 C4 1.3758(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.408(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3789(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.4027(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.4308(17) . ?
C9 C10 1.4349(17) . ?
C10 C11 1.3967(17) . ?
C10 C15 1.4052(17) . ?
C11 C12 1.3826(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3794(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.4017(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.4373(17) . ?
C16 C23 1.4765(17) . ?
C17 C18 1.3924(17) . ?
C17 C22 1.3969(18) . ?
C18 C19 1.3895(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.3833(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3860(19) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.3937(19) . ?
C23 C24 1.3964(19) . ?
C24 C25 1.394(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.377(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.380(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.3872(18) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.3961(17) . ?
C29 C34 1.4014(17) . ?
C30 C31 1.3924(18) . ?
C30 H30 0.9500 . ?
C31 C32 1.381(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.386(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.3855(19) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.4022(17) . ?
C35 C40 1.4062(17) . ?
C36 C37 1.3900(18) . ?
C36 H36 0.9500 . ?
C37 C38 1.385(2) . ?
C37 H37 0.9500 . ?
C38 C39 1.379(2) . ?
C38 H38 0.9500 . ?
C39 C40 1.3904(19) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C42 1.374(2) . ?
C41 C46 1.375(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.373(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.391(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.371(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.376(2) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 108.83(10) . . ?
C1 N1 B1 127.20(10) . . ?
C8 N1 B1 123.92(10) . . ?
C9 N2 C8 120.05(10) . . ?
C16 N3 C9 108.11(10) . . ?
C16 N3 B1 128.81(10) . . ?
C9 N3 B1 121.51(9) . . ?
N1 B1 C29 105.68(10) . . ?
N1 B1 N3 103.24(9) . . ?
C29 B1 N3 111.30(9) . . ?
N1 B1 C35 109.90(9) . . ?
C29 B1 C35 119.78(10) . . ?
N3 B1 C35 105.77(9) . . ?
N1 C1 C2 109.23(10) . . ?
N1 C1 C17 125.40(11) . . ?
C2 C1 C17 125.37(11) . . ?
C3 C2 C7 120.98(11) . . ?
C3 C2 C1 131.68(12) . . ?
C7 C2 C1 107.34(11) . . ?
C4 C3 C2 117.96(12) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 121.17(12) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.65(12) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 117.73(12) . . ?
C5 C6 H6 121.1 . . ?
C7 C6 H6 121.1 . . ?
C6 C7 C2 120.52(11) . . ?
C6 C7 C8 133.24(12) . . ?
C2 C7 C8 106.24(10) . . ?
N2 C8 N1 124.23(11) . . ?
N2 C8 C7 127.34(11) . . ?
N1 C8 C7 108.35(10) . . ?
N2 C9 N3 124.88(11) . . ?
N2 C9 C10 126.60(11) . . ?
N3 C9 C10 108.51(10) . . ?
C11 C10 C15 120.75(11) . . ?
C11 C10 C9 132.79(12) . . ?
C15 C10 C9 106.45(10) . . ?
C12 C11 C10 117.65(12) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
C11 C12 C13 121.59(12) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 121.37(12) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 117.51(12) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C14 C15 C10 121.11(11) . . ?
C14 C15 C16 131.71(12) . . ?
C10 C15 C16 107.18(11) . . ?
N3 C16 C15 109.75(10) . . ?
N3 C16 C23 126.37(11) . . ?
C15 C16 C23 123.88(11) . . ?
C18 C17 C22 119.12(11) . . ?
C18 C17 C1 122.22(11) . . ?
C22 C17 C1 118.59(11) . . ?
C19 C18 C17 120.34(12) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.03(12) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.99(12) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.29(12) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.12(12) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C28 C23 C24 119.04(12) . . ?
C28 C23 C16 121.97(12) . . ?
C24 C23 C16 118.91(12) . . ?
C25 C24 C23 120.11(14) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 120.17(14) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 120.04(13) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C28 120.48(14) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C23 120.12(13) . . ?
C27 C28 H28 119.9 . . ?
C23 C28 H28 119.9 . . ?
C30 C29 C34 116.81(11) . . ?
C30 C29 B1 125.52(11) . . ?
C34 C29 B1 117.55(10) . . ?
C31 C30 C29 121.58(12) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C32 C31 C30 120.34(13) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C31 C32 C33 119.28(13) . . ?
C31 C32 H32 120.4 . . ?
C33 C32 H32 120.4 . . ?
C34 C33 C32 120.19(13) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C29 121.80(12) . . ?
C33 C34 H34 119.1 . . ?
C29 C34 H34 119.1 . . ?
C36 C35 C40 116.06(11) . . ?
C36 C35 B1 122.82(10) . . ?
C40 C35 B1 120.99(11) . . ?
C37 C36 C35 122.19(12) . . ?
C37 C36 H36 118.9 . . ?
C35 C36 H36 118.9 . . ?
C38 C37 C36 120.12(13) . . ?
C38 C37 H37 119.9 . . ?
C36 C37 H37 119.9 . . ?
C39 C38 C37 119.30(12) . . ?
C39 C38 H38 120.3 . . ?
C37 C38 H38 120.3 . . ?
C38 C39 C40 120.47(12) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C39 C40 C35 121.86(12) . . ?
C39 C40 H40 119.1 . . ?
C35 C40 H40 119.1 . . ?
C42 C41 C46 120.04(16) . . ?
C42 C41 H41 120.0 . . ?
C46 C41 H41 120.0 . . ?
C43 C42 C41 119.99(16) . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C42 C43 C44 119.73(17) . . ?
C42 C43 H43 120.1 . . ?
C44 C43 H43 120.1 . . ?
C45 C44 C43 120.19(15) . . ?
C45 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
C44 C45 C46 119.55(16) . . ?
C44 C45 H45 120.2 . . ?
C46 C45 H45 120.2 . . ?
C41 C46 C45 120.48(17) . . ?
C41 C46 H46 119.8 . . ?
C45 C46 H46 119.8 . . ?

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 C29 49.66(14) . . . . ?
C8 N1 B1 C29 -127.41(11) . . . . ?
C1 N1 B1 N3 166.63(10) . . . . ?
C8 N1 B1 N3 -10.44(14) . . . . ?
C1 N1 B1 C35 -80.90(14) . . . . ?
C8 N1 B1 C35 102.03(12) . . . . ?
C16 N3 B1 N1 -179.54(11) . . . . ?
C9 N3 B1 N1 16.52(13) . . . . ?
C16 N3 B1 C29 -66.61(15) . . . . ?
C9 N3 B1 C29 129.46(11) . . . . ?
C16 N3 B1 C35 65.01(14) . . . . ?
C9 N3 B1 C35 -98.93(12) . . . . ?
C8 N1 C1 C2 0.88(13) . . . . ?
B1 N1 C1 C2 -176.55(10) . . . . ?
C8 N1 C1 C17 -179.23(11) . . . . ?
B1 N1 C1 C17 3.34(18) . . . . ?
N1 C1 C2 C3 179.62(12) . . . . ?
C17 C1 C2 C3 -0.3(2) . . . . ?
N1 C1 C2 C7 -1.52(13) . . . . ?
C17 C1 C2 C7 178.59(11) . . . . ?
C7 C2 C3 C4 0.33(18) . . . . ?
C1 C2 C3 C4 179.06(13) . . . . ?
C2 C3 C4 C5 -0.15(19) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C7 0.41(19) . . . . ?
C5 C6 C7 C2 -0.23(18) . . . . ?
C5 C6 C7 C8 178.89(13) . . . . ?
C3 C2 C7 C6 -0.14(18) . . . . ?
C1 C2 C7 C6 -179.15(11) . . . . ?
C3 C2 C7 C8 -179.48(11) . . . . ?
C1 C2 C7 C8 1.52(13) . . . . ?
C9 N2 C8 N1 4.91(18) . . . . ?
C9 N2 C8 C7 -171.36(11) . . . . ?
C1 N1 C8 N2 -176.79(11) . . . . ?
B1 N1 C8 N2 0.74(18) . . . . ?
C1 N1 C8 C7 0.09(13) . . . . ?
B1 N1 C8 C7 177.62(10) . . . . ?
C6 C7 C8 N2 -3.5(2) . . . . ?
C2 C7 C8 N2 175.74(12) . . . . ?
C6 C7 C8 N1 179.77(13) . . . . ?
C2 C7 C8 N1 -1.02(13) . . . . ?
C8 N2 C9 N3 2.30(18) . . . . ?
C8 N2 C9 C10 -179.22(11) . . . . ?
C16 N3 C9 N2 178.51(11) . . . . ?
B1 N3 C9 N2 -14.60(17) . . . . ?
C16 N3 C9 C10 -0.19(13) . . . . ?
B1 N3 C9 C10 166.69(10) . . . . ?
N2 C9 C10 C11 1.7(2) . . . . ?
N3 C9 C10 C11 -179.65(12) . . . . ?
N2 C9 C10 C15 -178.99(11) . . . . ?
N3 C9 C10 C15 -0.31(13) . . . . ?
C15 C10 C11 C12 -0.74(18) . . . . ?
C9 C10 C11 C12 178.53(12) . . . . ?
C10 C11 C12 C13 1.09(19) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 C15 -1.20(19) . . . . ?
C13 C14 C15 C10 1.53(18) . . . . ?
C13 C14 C15 C16 -179.34(13) . . . . ?
C11 C10 C15 C14 -0.57(18) . . . . ?
C9 C10 C15 C14 179.99(11) . . . . ?
C11 C10 C15 C16 -179.90(11) . . . . ?
C9 C10 C15 C16 0.66(13) . . . . ?
C9 N3 C16 C15 0.62(13) . . . . ?
B1 N3 C16 C15 -165.01(11) . . . . ?
C9 N3 C16 C23 -179.60(11) . . . . ?
B1 N3 C16 C23 14.77(19) . . . . ?
C14 C15 C16 N3 179.96(12) . . . . ?
C10 C15 C16 N3 -0.81(13) . . . . ?
C14 C15 C16 C23 0.2(2) . . . . ?
C10 C15 C16 C23 179.40(11) . . . . ?
N1 C1 C17 C18 70.02(16) . . . . ?
C2 C1 C17 C18 -110.10(14) . . . . ?
N1 C1 C17 C22 -112.88(14) . . . . ?
C2 C1 C17 C22 66.99(16) . . . . ?
C22 C17 C18 C19 1.95(18) . . . . ?
C1 C17 C18 C19 179.03(11) . . . . ?
C17 C18 C19 C20 1.14(19) . . . . ?
C18 C19 C20 C21 -2.8(2) . . . . ?
C19 C20 C21 C22 1.3(2) . . . . ?
C20 C21 C22 C17 1.8(2) . . . . ?
C18 C17 C22 C21 -3.43(19) . . . . ?
C1 C17 C22 C21 179.39(12) . . . . ?
N3 C16 C23 C28 58.68(18) . . . . ?
C15 C16 C23 C28 -121.57(14) . . . . ?
N3 C16 C23 C24 -124.51(14) . . . . ?
C15 C16 C23 C24 55.24(17) . . . . ?
C28 C23 C24 C25 -2.58(19) . . . . ?
C16 C23 C24 C25 -179.48(12) . . . . ?
C23 C24 C25 C26 1.5(2) . . . . ?
C24 C25 C26 C27 0.4(2) . . . . ?
C25 C26 C27 C28 -1.0(2) . . . . ?
C26 C27 C28 C23 -0.1(2) . . . . ?
C24 C23 C28 C27 1.91(18) . . . . ?
C16 C23 C28 C27 178.71(12) . . . . ?
N1 B1 C29 C30 -118.03(12) . . . . ?
N3 B1 C29 C30 130.58(12) . . . . ?
C35 B1 C29 C30 6.58(18) . . . . ?
N1 B1 C29 C34 57.77(13) . . . . ?
N3 B1 C29 C34 -53.62(14) . . . . ?
C35 B1 C29 C34 -177.63(11) . . . . ?
C34 C29 C30 C31 1.36(18) . . . . ?
B1 C29 C30 C31 177.18(12) . . . . ?
C29 C30 C31 C32 -0.8(2) . . . . ?
C30 C31 C32 C33 0.0(2) . . . . ?
C31 C32 C33 C34 0.1(2) . . . . ?
C32 C33 C34 C29 0.6(2) . . . . ?
C30 C29 C34 C33 -1.26(19) . . . . ?
B1 C29 C34 C33 -177.43(12) . . . . ?
N1 B1 C35 C36 164.40(10) . . . . ?
C29 B1 C35 C36 41.83(16) . . . . ?
N3 B1 C35 C36 -84.79(13) . . . . ?
N1 B1 C35 C40 -19.84(15) . . . . ?
C29 B1 C35 C40 -142.41(11) . . . . ?
N3 B1 C35 C40 90.97(12) . . . . ?
C40 C35 C36 C37 0.24(18) . . . . ?
B1 C35 C36 C37 176.19(11) . . . . ?
C35 C36 C37 C38 0.0(2) . . . . ?
C36 C37 C38 C39 -0.1(2) . . . . ?
C37 C38 C39 C40 0.0(2) . . . . ?
C38 C39 C40 C35 0.2(2) . . . . ?
C36 C35 C40 C39 -0.35(18) . . . . ?
B1 C35 C40 C39 -176.39(11) . . . . ?
C46 C41 C42 C43 -0.4(3) . . . . ?
C41 C42 C43 C44 -0.7(3) . . . . ?
C42 C43 C44 C45 1.1(3) . . . . ?
C43 C44 C45 C46 -0.2(3) . . . . ?
C42 C41 C46 C45 1.3(3) . . . . ?
C44 C45 C46 C41 -1.0(3) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_RD001_cmpd6
_database_code_depnum_ccdc_archive 'CCDC 1955379'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2019-09-23 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H18 B Cl2 N3'
_chemical_formula_sum            'C28 H18 B Cl2 N3'
_chemical_formula_weight         478.16

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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   9.965(2)
_cell_length_b                   10.359(3)
_cell_length_c                   11.761(3)
_cell_angle_alpha                79.445(3)
_cell_angle_beta                 86.088(3)
_cell_angle_gamma                67.630(3)
_cell_volume                     1103.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    3447
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.21

_exptl_crystal_description       'thin rectangular rod'
_exptl_crystal_colour            gold
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.318
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6446
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13301
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.761
_diffrn_reflns_theta_max         28.812
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5269
_reflns_number_gt                3207
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_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         5269
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
Cl1 Cl 0.03803(7) 0.67828(7) 0.47107(6) 0.0303(2) Uani 1 1 d . . . . .
Cl2 Cl 0.35105(8) 0.65562(7) 0.42869(6) 0.0299(2) Uani 1 1 d . . . . .
B1 B 0.2313(3) 0.5595(3) 0.4850(3) 0.0211(7) Uani 1 1 d . . . . .
N1 N 0.2540(2) 0.4355(2) 0.42006(18) 0.0201(5) Uani 1 1 d . . . . .
N2 N 0.3373(2) 0.2510(2) 0.58647(18) 0.0210(5) Uani 1 1 d . . . . .
N3 N 0.2727(2) 0.4932(2) 0.61345(18) 0.0198(5) Uani 1 1 d . . . . .
C1 C 0.2148(3) 0.4421(3) 0.3098(2) 0.0213(6) Uani 1 1 d . . . . .
C2 C 0.2375(3) 0.3022(3) 0.2924(2) 0.0224(6) Uani 1 1 d . . . . .
C3 C 0.2140(3) 0.2526(3) 0.1953(2) 0.0260(6) Uani 1 1 d . . . . .
H3 H 0.1777 0.3149 0.1248 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2461(3) 0.1092(3) 0.2071(2) 0.0268(6) Uani 1 1 d . . . . .
H4 H 0.2320 0.0721 0.1428 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2980(3) 0.0175(3) 0.3093(2) 0.0276(7) Uani 1 1 d . . . . .
H5 H 0.3176 -0.0804 0.3132 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3223(3) 0.0637(3) 0.4056(2) 0.0230(6) Uani 1 1 d . . . . .
H6 H 0.3575 -0.0003 0.4756 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2934(3) 0.2083(3) 0.3967(2) 0.0214(6) Uani 1 1 d . . . . .
C8 C 0.3009(3) 0.2932(3) 0.4763(2) 0.0207(6) Uani 1 1 d . . . . .
C9 C 0.3255(3) 0.3463(3) 0.6520(2) 0.0205(6) Uani 1 1 d . . . . .
C10 C 0.3674(3) 0.3191(3) 0.7702(2) 0.0214(6) Uani 1 1 d . . . . .
C11 C 0.4267(3) 0.1944(3) 0.8506(2) 0.0237(6) Uani 1 1 d . . . . .
H11 H 0.4451 0.1045 0.8304 0.028 Uiso 1 1 calc R U . . .
C12 C 0.4574(3) 0.2055(3) 0.9587(2) 0.0267(6) Uani 1 1 d . . . . .
H12 H 0.4999 0.1219 1.0138 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4271(3) 0.3390(3) 0.9904(2) 0.0282(7) Uani 1 1 d . . . . .
H13 H 0.4486 0.3432 1.0668 0.034 Uiso 1 1 calc R U . . .
C14 C 0.3672(3) 0.4627(3) 0.9134(2) 0.0241(6) Uani 1 1 d . . . . .
H14 H 0.3447 0.5522 0.9359 0.029 Uiso 1 1 calc R U . . .
C15 C 0.3405(3) 0.4525(3) 0.8013(2) 0.0204(6) Uani 1 1 d . . . . .
C16 C 0.2835(3) 0.5583(3) 0.7015(2) 0.0206(6) Uani 1 1 d . . . . .
C17 C 0.1566(3) 0.5704(3) 0.2206(2) 0.0234(6) Uani 1 1 d . . . . .
C18 C 0.2359(3) 0.6524(3) 0.1738(2) 0.0272(6) Uani 1 1 d . . . . .
H18 H 0.3294 0.6317 0.2036 0.033 Uiso 1 1 calc R U . . .
C19 C 0.1785(3) 0.7653(3) 0.0827(2) 0.0324(7) Uani 1 1 d . . . . .
H19 H 0.2334 0.8205 0.0501 0.039 Uiso 1 1 calc R U . . .
C20 C 0.0420(3) 0.7963(3) 0.0404(3) 0.0352(7) Uani 1 1 d . . . . .
H20 H 0.0030 0.8729 -0.0216 0.042 Uiso 1 1 calc R U . . .
C21 C -0.0383(3) 0.7163(3) 0.0878(3) 0.0356(7) Uani 1 1 d . . . . .
H21 H -0.1331 0.7394 0.0594 0.043 Uiso 1 1 calc R U . . .
C22 C 0.0186(3) 0.6026(3) 0.1767(2) 0.0300(7) Uani 1 1 d . . . . .
H22 H -0.0362 0.5467 0.2076 0.036 Uiso 1 1 calc R U . . .
C23 C 0.2502(3) 0.7108(3) 0.6975(2) 0.0216(6) Uani 1 1 d . . . . .
C24 C 0.3659(3) 0.7485(3) 0.7183(2) 0.0263(6) Uani 1 1 d . . . . .
H24 H 0.4613 0.6784 0.7278 0.032 Uiso 1 1 calc R U . . .
C25 C 0.3416(3) 0.8882(3) 0.7251(2) 0.0285(7) Uani 1 1 d . . . . .
H25 H 0.4201 0.9133 0.7403 0.034 Uiso 1 1 calc R U . . .
C26 C 0.2027(3) 0.9908(3) 0.7096(3) 0.0318(7) Uani 1 1 d . . . . .
H26 H 0.1861 1.0866 0.7130 0.038 Uiso 1 1 calc R U . . .
C27 C 0.0876(3) 0.9532(3) 0.6888(3) 0.0339(7) Uani 1 1 d . . . . .
H27 H -0.0077 1.0232 0.6787 0.041 Uiso 1 1 calc R U . . .
C28 C 0.1120(3) 0.8135(3) 0.6828(2) 0.0296(7) Uani 1 1 d . . . . .
H28 H 0.0333 0.7883 0.6686 0.035 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 B1 1.848(3) . ?
Cl2 B1 1.847(3) . ?
B1 N1 1.549(4) . ?
B1 N3 1.553(4) . ?
N1 C1 1.362(3) . ?
N1 C8 1.410(3) . ?
N2 C8 1.318(3) . ?
N2 C9 1.327(3) . ?
N3 C16 1.365(3) . ?
N3 C9 1.403(3) . ?
C1 C2 1.431(4) . ?
C1 C17 1.479(4) . ?
C2 C3 1.402(4) . ?
C2 C7 1.416(4) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.421(4) . ?
C9 C10 1.426(4) . ?
C10 C11 1.401(4) . ?
C10 C15 1.415(4) . ?
C11 C12 1.361(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.414(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.431(4) . ?
C16 C23 1.478(4) . ?
C17 C18 1.390(4) . ?
C17 C22 1.398(4) . ?
C18 C19 1.399(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.381(4) . ?
C23 C24 1.399(4) . ?
C24 C25 1.390(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.393(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.387(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 B1 N3 106.8(2) . . ?
N1 B1 Cl2 111.69(19) . . ?
N3 B1 Cl2 107.95(18) . . ?
N1 B1 Cl1 107.89(18) . . ?
N3 B1 Cl1 111.07(19) . . ?
Cl2 B1 Cl1 111.34(16) . . ?
C1 N1 C8 108.6(2) . . ?
C1 N1 B1 128.3(2) . . ?
C8 N1 B1 122.5(2) . . ?
C8 N2 C9 119.5(2) . . ?
C16 N3 C9 108.9(2) . . ?
C16 N3 B1 128.5(2) . . ?
C9 N3 B1 122.1(2) . . ?
N1 C1 C2 108.7(2) . . ?
N1 C1 C17 127.1(2) . . ?
C2 C1 C17 124.2(2) . . ?
C3 C2 C7 121.2(2) . . ?
C3 C2 C1 131.0(3) . . ?
C7 C2 C1 107.7(2) . . ?
C4 C3 C2 116.7(3) . . ?
C4 C3 H3 121.6 . . ?
C2 C3 H3 121.6 . . ?
C3 C4 C5 122.3(3) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 117.6(3) . . ?
C5 C6 H6 121.2 . . ?
C7 C6 H6 121.2 . . ?
C6 C7 C2 120.2(2) . . ?
C6 C7 C8 133.4(3) . . ?
C2 C7 C8 106.3(2) . . ?
N2 C8 N1 124.2(2) . . ?
N2 C8 C7 127.0(2) . . ?
N1 C8 C7 108.6(2) . . ?
N2 C9 N3 124.7(2) . . ?
N2 C9 C10 126.9(2) . . ?
N3 C9 C10 108.4(2) . . ?
C11 C10 C15 120.4(2) . . ?
C11 C10 C9 133.0(2) . . ?
C15 C10 C9 106.5(2) . . ?
C12 C11 C10 118.2(3) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 117.7(2) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C14 C15 C10 120.8(2) . . ?
C14 C15 C16 131.7(2) . . ?
C10 C15 C16 107.5(2) . . ?
N3 C16 C15 108.6(2) . . ?
N3 C16 C23 127.6(2) . . ?
C15 C16 C23 123.7(2) . . ?
C18 C17 C22 119.4(3) . . ?
C18 C17 C1 123.3(2) . . ?
C22 C17 C1 117.2(2) . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 119.9(3) . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C28 C23 C24 119.6(2) . . ?
C28 C23 C16 123.7(2) . . ?
C24 C23 C16 116.5(2) . . ?
C25 C24 C23 120.2(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 119.9(3) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C28 C27 C26 120.1(3) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C23 C28 C27 120.4(3) . . ?
C23 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?

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
N3 B1 N1 C1 170.9(2) . . . . ?
Cl2 B1 N1 C1 -71.3(3) . . . . ?
Cl1 B1 N1 C1 51.4(3) . . . . ?
N3 B1 N1 C8 1.2(3) . . . . ?
Cl2 B1 N1 C8 119.0(2) . . . . ?
Cl1 B1 N1 C8 -118.3(2) . . . . ?
N1 B1 N3 C16 173.2(2) . . . . ?
Cl2 B1 N3 C16 52.9(3) . . . . ?
Cl1 B1 N3 C16 -69.4(3) . . . . ?
N1 B1 N3 C9 2.5(3) . . . . ?
Cl2 B1 N3 C9 -117.8(2) . . . . ?
Cl1 B1 N3 C9 119.9(2) . . . . ?
C8 N1 C1 C2 -0.5(3) . . . . ?
B1 N1 C1 C2 -171.4(2) . . . . ?
C8 N1 C1 C17 178.7(2) . . . . ?
B1 N1 C1 C17 7.9(4) . . . . ?
N1 C1 C2 C3 179.8(3) . . . . ?
C17 C1 C2 C3 0.5(5) . . . . ?
N1 C1 C2 C7 -0.4(3) . . . . ?
C17 C1 C2 C7 -179.7(2) . . . . ?
C7 C2 C3 C4 0.9(4) . . . . ?
C1 C2 C3 C4 -179.4(3) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C5 C6 C7 C2 1.7(4) . . . . ?
C5 C6 C7 C8 177.8(3) . . . . ?
C3 C2 C7 C6 -1.9(4) . . . . ?
C1 C2 C7 C6 178.3(2) . . . . ?
C3 C2 C7 C8 -179.0(2) . . . . ?
C1 C2 C7 C8 1.2(3) . . . . ?
C9 N2 C8 N1 2.4(4) . . . . ?
C9 N2 C8 C7 -173.6(2) . . . . ?
C1 N1 C8 N2 -175.3(2) . . . . ?
B1 N1 C8 N2 -3.9(4) . . . . ?
C1 N1 C8 C7 1.3(3) . . . . ?
B1 N1 C8 C7 172.8(2) . . . . ?
C6 C7 C8 N2 -1.6(5) . . . . ?
C2 C7 C8 N2 175.0(2) . . . . ?
C6 C7 C8 N1 -178.1(3) . . . . ?
C2 C7 C8 N1 -1.6(3) . . . . ?
C8 N2 C9 N3 1.6(4) . . . . ?
C8 N2 C9 C10 -176.2(2) . . . . ?
C16 N3 C9 N2 -176.5(2) . . . . ?
B1 N3 C9 N2 -4.2(4) . . . . ?
C16 N3 C9 C10 1.6(3) . . . . ?
B1 N3 C9 C10 174.0(2) . . . . ?
N2 C9 C10 C11 -1.6(5) . . . . ?
N3 C9 C10 C11 -179.7(3) . . . . ?
N2 C9 C10 C15 177.3(2) . . . . ?
N3 C9 C10 C15 -0.8(3) . . . . ?
C15 C10 C11 C12 0.0(4) . . . . ?
C9 C10 C11 C12 178.8(3) . . . . ?
C10 C11 C12 C13 1.6(4) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C13 C14 C15 -1.7(4) . . . . ?
C13 C14 C15 C10 3.2(4) . . . . ?
C13 C14 C15 C16 -178.3(3) . . . . ?
C11 C10 C15 C14 -2.5(4) . . . . ?
C9 C10 C15 C14 178.5(2) . . . . ?
C11 C10 C15 C16 178.8(2) . . . . ?
C9 C10 C15 C16 -0.3(3) . . . . ?
C9 N3 C16 C15 -1.8(3) . . . . ?
B1 N3 C16 C15 -173.5(2) . . . . ?
C9 N3 C16 C23 175.5(2) . . . . ?
B1 N3 C16 C23 3.8(4) . . . . ?
C14 C15 C16 N3 -177.3(3) . . . . ?
C10 C15 C16 N3 1.3(3) . . . . ?
C14 C15 C16 C23 5.3(4) . . . . ?
C10 C15 C16 C23 -176.1(2) . . . . ?
N1 C1 C17 C18 65.1(4) . . . . ?
C2 C1 C17 C18 -115.7(3) . . . . ?
N1 C1 C17 C22 -119.7(3) . . . . ?
C2 C1 C17 C22 59.5(4) . . . . ?
C22 C17 C18 C19 -0.6(4) . . . . ?
C1 C17 C18 C19 174.5(2) . . . . ?
C17 C18 C19 C20 0.8(4) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C22 -1.3(5) . . . . ?
C20 C21 C22 C17 1.5(5) . . . . ?
C18 C17 C22 C21 -0.6(4) . . . . ?
C1 C17 C22 C21 -176.0(3) . . . . ?
N3 C16 C23 C28 67.5(4) . . . . ?
C15 C16 C23 C28 -115.6(3) . . . . ?
N3 C16 C23 C24 -117.2(3) . . . . ?
C15 C16 C23 C24 59.7(3) . . . . ?
C28 C23 C24 C25 0.5(4) . . . . ?
C16 C23 C24 C25 -175.0(3) . . . . ?
C23 C24 C25 C26 -0.9(4) . . . . ?
C24 C25 C26 C27 0.9(4) . . . . ?
C25 C26 C27 C28 -0.5(4) . . . . ?
C24 C23 C28 C27 -0.1(4) . . . . ?
C16 C23 C28 C27 175.1(3) . . . . ?
C26 C27 C28 C23 0.1(4) . . . . ?

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_LBA001_cmpd4HCl
_database_code_depnum_ccdc_archive 'CCDC 1955378'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2019-09-23 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

#============================================================================== 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C32 H24 N3), C H2 Cl2, 2(Cl)'
_chemical_formula_sum            'C65 H50 Cl4 N6'
_chemical_formula_weight         1056.91

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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   9.4100(3)
_cell_length_b                   10.4509(4)
_cell_length_c                   13.6039(5)
_cell_angle_alpha                73.214(2)
_cell_angle_beta                 87.718(2)
_cell_angle_gamma                79.175(2)
_cell_volume                     1257.90(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.79

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             550
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.287
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6729
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22450
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.564
_diffrn_reflns_theta_max         28.944
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6101
_reflns_number_gt                4883
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.4442P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6101
_refine_ls_number_parameters     360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.25175(4) 0.53471(4) 0.26215(3) 0.02410(11) Uani 1 1 d . . . . .
C33 C 0.0702(4) 0.5202(4) 0.0427(3) 0.0297(8) Uani 0.5 1 d . . P A -1
H33A H 0.1684 0.5319 0.0176 0.036 Uiso 0.5 1 calc R U P A -1
H33B H 0.0487 0.5639 0.0985 0.036 Uiso 0.5 1 calc R U P A -1
Cl2 Cl -0.0569(2) 0.6003(2) -0.05857(13) 0.0493(5) Uani 0.5 1 d . . P A -1
Cl3 Cl 0.0656(2) 0.34727(16) 0.09072(12) 0.0351(3) Uani 0.5 1 d . . P A -1
N1 N 0.37907(13) 0.21896(13) 0.53916(10) 0.0179(3) Uani 1 1 d . . . . .
N2 N 0.14646(14) 0.32919(14) 0.45194(11) 0.0181(3) Uani 1 1 d . . . . .
H2N H 0.172(2) 0.380(2) 0.3937(18) 0.042(6) Uiso 1 1 d . . . . .
N3 N 0.44385(14) 0.25443(14) 0.35802(10) 0.0203(3) Uani 1 1 d . . . . .
H3N H 0.376(2) 0.326(2) 0.3266(17) 0.047(6) Uiso 1 1 d . . . . .
C1 C 0.23782(16) 0.26244(15) 0.53694(12) 0.0175(3) Uani 1 1 d . . . . .
C2 C 0.00691(16) 0.34495(16) 0.48317(12) 0.0182(3) Uani 1 1 d . . . . .
C3 C 0.00532(16) 0.28651(16) 0.59000(12) 0.0196(3) Uani 1 1 d . . . . .
H3 H -0.0789 0.2814 0.6308 0.024 Uiso 1 1 calc R U . . .
C4 C 0.14630(16) 0.23768(15) 0.62606(12) 0.0179(3) Uani 1 1 d . . . . .
C5 C -0.11568(16) 0.40896(15) 0.41303(12) 0.0182(3) Uani 1 1 d . . . . .
C6 C -0.25463(16) 0.43637(16) 0.45273(13) 0.0201(3) Uani 1 1 d . . . . .
H6 H -0.2676 0.4155 0.5249 0.024 Uiso 1 1 calc R U . . .
C7 C -0.37261(17) 0.49388(16) 0.38665(13) 0.0223(3) Uani 1 1 d . . . . .
H7 H -0.4664 0.5117 0.4139 0.027 Uiso 1 1 calc R U . . .
C8 C -0.35521(18) 0.52566(17) 0.28146(13) 0.0250(4) Uani 1 1 d . . . . .
H8 H -0.4368 0.5647 0.2367 0.030 Uiso 1 1 calc R U . . .
C9 C -0.21822(18) 0.50043(18) 0.24131(13) 0.0255(4) Uani 1 1 d . . . . .
H9 H -0.2060 0.5230 0.1690 0.031 Uiso 1 1 calc R U . . .
C10 C -0.09920(17) 0.44240(17) 0.30655(13) 0.0225(3) Uani 1 1 d . . . . .
H10 H -0.0058 0.4252 0.2787 0.027 Uiso 1 1 calc R U . . .
C11 C 0.18979(17) 0.17762(16) 0.73427(12) 0.0193(3) Uani 1 1 d . . . . .
C12 C 0.32989(18) 0.10868(18) 0.76640(13) 0.0272(4) Uani 1 1 d . . . . .
H12 H 0.4000 0.0933 0.7169 0.033 Uiso 1 1 calc R U . . .
C13 C 0.3673(2) 0.0626(2) 0.86981(15) 0.0371(5) Uani 1 1 d . . . . .
H13 H 0.4636 0.0184 0.8905 0.044 Uiso 1 1 calc R U . . .
C14 C 0.2649(2) 0.0807(2) 0.94355(14) 0.0359(4) Uani 1 1 d . . . . .
H14 H 0.2910 0.0493 1.0144 0.043 Uiso 1 1 calc R U . . .
C15 C 0.1250(2) 0.14468(19) 0.91274(14) 0.0313(4) Uani 1 1 d . . . . .
H15 H 0.0540 0.1551 0.9629 0.038 Uiso 1 1 calc R U . . .
C16 C 0.08728(18) 0.19366(18) 0.80970(13) 0.0253(4) Uani 1 1 d . . . . .
H16 H -0.0090 0.2387 0.7897 0.030 Uiso 1 1 calc R U . . .
C17 C 0.47067(16) 0.21397(16) 0.46332(12) 0.0188(3) Uani 1 1 d . . . . .
C18 C 0.56600(16) 0.21495(16) 0.30920(13) 0.0210(3) Uani 1 1 d . . . . .
C19 C 0.67415(17) 0.14378(17) 0.38376(13) 0.0223(3) Uani 1 1 d . . . . .
H19 H 0.7687 0.1019 0.3705 0.027 Uiso 1 1 calc R U . . .
C20 C 0.61987(16) 0.14497(16) 0.47946(13) 0.0202(3) Uani 1 1 d . . . . .
C21 C 0.57314(17) 0.24637(17) 0.19791(13) 0.0233(3) Uani 1 1 d . . . . .
C22 C 0.4480(2) 0.2843(2) 0.13705(14) 0.0330(4) Uani 1 1 d . . . . .
H22 H 0.3558 0.2905 0.1683 0.040 Uiso 1 1 calc R U . . .
C23 C 0.4573(2) 0.3130(2) 0.03145(15) 0.0393(5) Uani 1 1 d . . . . .
H23 H 0.3714 0.3384 -0.0094 0.047 Uiso 1 1 calc R U . . .
C24 C 0.5906(2) 0.3050(2) -0.01498(15) 0.0390(5) Uani 1 1 d . . . . .
H24 H 0.5967 0.3262 -0.0876 0.047 Uiso 1 1 calc R U . . .
C25 C 0.7142(2) 0.2662(3) 0.04486(17) 0.0546(7) Uani 1 1 d . . . . .
H25 H 0.8060 0.2599 0.0132 0.066 Uiso 1 1 calc R U . . .
C26 C 0.7067(2) 0.2363(3) 0.15004(15) 0.0415(5) Uani 1 1 d . . . . .
H26 H 0.7932 0.2085 0.1903 0.050 Uiso 1 1 calc R U . . .
C27 C 0.69814(16) 0.08781(16) 0.57790(13) 0.0208(3) Uani 1 1 d . . . . .
C28 C 0.81379(18) -0.02191(17) 0.58972(14) 0.0267(4) Uani 1 1 d . . . . .
H28 H 0.8388 -0.0601 0.5345 0.032 Uiso 1 1 calc R U . . .
C29 C 0.89156(19) -0.07496(19) 0.68079(15) 0.0323(4) Uani 1 1 d . . . . .
H29 H 0.9685 -0.1505 0.6883 0.039 Uiso 1 1 calc R U . . .
C30 C 0.85845(19) -0.01896(19) 0.76130(15) 0.0320(4) Uani 1 1 d . . . . .
H30 H 0.9123 -0.0562 0.8239 0.038 Uiso 1 1 calc R U . . .
C31 C 0.74652(18) 0.09161(18) 0.75047(14) 0.0270(4) Uani 1 1 d . . . . .
H31 H 0.7246 0.1311 0.8053 0.032 Uiso 1 1 calc R U . . .
C32 C 0.66679(17) 0.14438(17) 0.65978(13) 0.0232(3) Uani 1 1 d . . . . .
H32 H 0.5899 0.2198 0.6529 0.028 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
C33 Cl3 1.743(4) . ?
C33 Cl2 1.766(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
N1 C1 1.3200(19) . ?
N1 C17 1.3243(19) . ?
N2 C2 1.3589(19) . ?
N2 C1 1.397(2) . ?
N2 H2N 0.87(2) . ?
N3 C18 1.3609(19) . ?
N3 C17 1.390(2) . ?
N3 H3N 0.90(2) . ?
C1 C4 1.448(2) . ?
C2 C3 1.405(2) . ?
C2 C5 1.455(2) . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C11 1.465(2) . ?
C5 C10 1.398(2) . ?
C5 C6 1.406(2) . ?
C6 C7 1.385(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.398(2) . ?
C11 C16 1.404(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C20 1.446(2) . ?
C18 C19 1.407(2) . ?
C18 C21 1.455(2) . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 C27 1.464(2) . ?
C21 C26 1.392(2) . ?
C21 C22 1.394(2) . ?
C22 C23 1.383(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.374(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.375(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.401(2) . ?
C27 C32 1.402(2) . ?
C28 C29 1.379(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.383(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.387(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.384(2) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl3 C33 Cl2 111.2(2) . . ?
Cl3 C33 H33A 109.4 . . ?
Cl2 C33 H33A 109.4 . . ?
Cl3 C33 H33B 109.4 . . ?
Cl2 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C1 N1 C17 130.40(14) . . ?
C2 N2 C1 109.40(13) . . ?
C2 N2 H2N 121.3(14) . . ?
C1 N2 H2N 125.5(15) . . ?
C18 N3 C17 109.39(13) . . ?
C18 N3 H3N 121.7(15) . . ?
C17 N3 H3N 123.1(15) . . ?
N1 C1 N2 128.65(14) . . ?
N1 C1 C4 124.38(14) . . ?
N2 C1 C4 106.79(13) . . ?
N2 C2 C3 108.46(13) . . ?
N2 C2 C5 123.31(14) . . ?
C3 C2 C5 128.21(14) . . ?
C4 C3 C2 108.91(14) . . ?
C4 C3 H3 125.5 . . ?
C2 C3 H3 125.5 . . ?
C3 C4 C1 106.40(13) . . ?
C3 C4 C11 125.24(14) . . ?
C1 C4 C11 128.33(13) . . ?
C10 C5 C6 118.88(14) . . ?
C10 C5 C2 121.57(14) . . ?
C6 C5 C2 119.54(14) . . ?
C7 C6 C5 119.99(15) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 120.64(15) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 119.89(15) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 120.10(16) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C5 120.49(15) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C12 C11 C16 118.18(15) . . ?
C12 C11 C4 123.24(14) . . ?
C16 C11 C4 118.54(14) . . ?
C13 C12 C11 120.56(16) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.54(17) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.32(17) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.62(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.72(16) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N1 C17 N3 129.29(14) . . ?
N1 C17 C20 123.32(14) . . ?
N3 C17 C20 106.92(13) . . ?
N3 C18 C19 108.41(14) . . ?
N3 C18 C21 122.34(14) . . ?
C19 C18 C21 129.25(14) . . ?
C20 C19 C18 108.63(14) . . ?
C20 C19 H19 125.7 . . ?
C18 C19 H19 125.7 . . ?
C19 C20 C17 106.56(14) . . ?
C19 C20 C27 126.72(14) . . ?
C17 C20 C27 126.71(14) . . ?
C26 C21 C22 118.50(16) . . ?
C26 C21 C18 120.18(16) . . ?
C22 C21 C18 121.31(15) . . ?
C23 C22 C21 120.34(17) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 120.43(18) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.37(18) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.87(18) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C21 120.47(18) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C28 C27 C32 118.27(15) . . ?
C28 C27 C20 119.57(15) . . ?
C32 C27 C20 122.05(14) . . ?
C29 C28 C27 120.58(16) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 120.49(16) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C31 119.90(17) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C32 C31 C30 119.96(16) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C27 120.78(15) . . ?
C31 C32 H32 119.6 . . ?
C27 C32 H32 119.6 . . ?

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
C17 N1 C1 N2 -7.4(3) . . . . ?
C17 N1 C1 C4 167.17(15) . . . . ?
C2 N2 C1 N1 174.58(15) . . . . ?
C2 N2 C1 C4 -0.70(17) . . . . ?
C1 N2 C2 C3 -0.72(17) . . . . ?
C1 N2 C2 C5 -179.00(13) . . . . ?
N2 C2 C3 C4 1.95(18) . . . . ?
C5 C2 C3 C4 -179.89(15) . . . . ?
C2 C3 C4 C1 -2.32(17) . . . . ?
C2 C3 C4 C11 175.83(14) . . . . ?
N1 C1 C4 C3 -173.67(14) . . . . ?
N2 C1 C4 C3 1.86(17) . . . . ?
N1 C1 C4 C11 8.2(3) . . . . ?
N2 C1 C4 C11 -176.22(14) . . . . ?
N2 C2 C5 C10 8.8(2) . . . . ?
C3 C2 C5 C10 -169.13(15) . . . . ?
N2 C2 C5 C6 -172.13(14) . . . . ?
C3 C2 C5 C6 10.0(2) . . . . ?
C10 C5 C6 C7 0.9(2) . . . . ?
C2 C5 C6 C7 -178.24(14) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C5 -0.1(3) . . . . ?
C6 C5 C10 C9 -0.6(2) . . . . ?
C2 C5 C10 C9 178.48(15) . . . . ?
C3 C4 C11 C12 168.65(16) . . . . ?
C1 C4 C11 C12 -13.6(3) . . . . ?
C3 C4 C11 C16 -13.5(2) . . . . ?
C1 C4 C11 C16 164.26(15) . . . . ?
C16 C11 C12 C13 -2.6(3) . . . . ?
C4 C11 C12 C13 175.30(17) . . . . ?
C11 C12 C13 C14 1.9(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 -1.7(3) . . . . ?
C14 C15 C16 C11 1.0(3) . . . . ?
C12 C11 C16 C15 1.2(3) . . . . ?
C4 C11 C16 C15 -176.82(16) . . . . ?
C1 N1 C17 N3 0.4(3) . . . . ?
C1 N1 C17 C20 -170.71(15) . . . . ?
C18 N3 C17 N1 -172.23(16) . . . . ?
C18 N3 C17 C20 0.00(17) . . . . ?
C17 N3 C18 C19 1.68(18) . . . . ?
C17 N3 C18 C21 -178.14(15) . . . . ?
N3 C18 C19 C20 -2.79(18) . . . . ?
C21 C18 C19 C20 177.01(16) . . . . ?
C18 C19 C20 C17 2.72(18) . . . . ?
C18 C19 C20 C27 -177.18(15) . . . . ?
N1 C17 C20 C19 171.11(15) . . . . ?
N3 C17 C20 C19 -1.70(17) . . . . ?
N1 C17 C20 C27 -9.0(3) . . . . ?
N3 C17 C20 C27 178.20(15) . . . . ?
N3 C18 C21 C26 163.28(18) . . . . ?
C19 C18 C21 C26 -16.5(3) . . . . ?
N3 C18 C21 C22 -18.0(3) . . . . ?
C19 C18 C21 C22 162.20(18) . . . . ?
C26 C21 C22 C23 -0.9(3) . . . . ?
C18 C21 C22 C23 -179.65(18) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C22 C23 C24 C25 1.0(3) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C24 C25 C26 C21 -0.7(4) . . . . ?
C22 C21 C26 C25 1.4(3) . . . . ?
C18 C21 C26 C25 -179.8(2) . . . . ?
C19 C20 C27 C28 -27.5(2) . . . . ?
C17 C20 C27 C28 152.59(16) . . . . ?
C19 C20 C27 C32 148.65(17) . . . . ?
C17 C20 C27 C32 -31.2(2) . . . . ?
C32 C27 C28 C29 1.9(3) . . . . ?
C20 C27 C28 C29 178.21(16) . . . . ?
C27 C28 C29 C30 -1.3(3) . . . . ?
C28 C29 C30 C31 -0.2(3) . . . . ?
C29 C30 C31 C32 1.0(3) . . . . ?
C30 C31 C32 C27 -0.3(3) . . . . ?
C28 C27 C32 C31 -1.1(2) . . . . ?
C20 C27 C32 C31 -177.31(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N Cl1 0.87(2) 2.25(2) 3.1070(15) 169(2) .
N3 H3N Cl1 0.90(2) 2.22(2) 3.0888(15) 164(2) .

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.055

