# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_AL43
_database_code_depnum_ccdc_archive 'CCDC 1830512'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H16 B N S'
_chemical_formula_sum            'C23 H16 B N S'
_chemical_formula_weight         349.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
_chemical_absolute_configuration ad
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100(1)
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.6076(3)
_cell_length_b                   9.4500(5)
_cell_length_c                   10.8046(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.428(3)
_cell_angle_gamma                90
_cell_volume                     866.99(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    20114
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.70
_cell_measurement_theta_min      2.16
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.03509
_exptl_absorpt_correction_T_min  0.89452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'MULABS / PLATON Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. Spek, A.L. (2009). Acta Cryst. D65, 148-155.'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.275
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14213
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.269
_diffrn_reflns_theta_min         2.399
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.889
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4852
_reflns_number_total             5160
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 2187 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5160
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.0456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0705
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.59921(4) 0.41481(4) 0.93710(4) 0.01969(9) Uani 1 1 d . . . . .
N1 N 0.64506(16) 0.83903(15) 0.71836(12) 0.0187(3) Uani 1 1 d . . . . .
C1 C 0.71754(18) 0.60550(18) 0.65618(14) 0.0179(3) Uani 1 1 d . . . . .
C2 C 0.7643(2) 0.46710(19) 0.63741(15) 0.0205(3) Uani 1 1 d . . . . .
H2 H 0.7496 0.3955 0.6961 0.025 Uiso 1 1 calc R . . . .
C3 C 0.8327(2) 0.4331(2) 0.53288(15) 0.0249(4) Uani 1 1 d . . . . .
H3 H 0.8657 0.3387 0.5216 0.030 Uiso 1 1 calc R . . . .
C4 C 0.8532(2) 0.5364(2) 0.44456(16) 0.0279(4) Uani 1 1 d . . . . .
H4 H 0.8996 0.5115 0.3736 0.033 Uiso 1 1 calc R . . . .
C5 C 0.8064(2) 0.6747(2) 0.45941(16) 0.0255(3) Uani 1 1 d . . . . .
H5 H 0.8186 0.7451 0.3990 0.031 Uiso 1 1 calc R . . . .
C6 C 0.74070(18) 0.70766(18) 0.56600(14) 0.0196(3) Uani 1 1 d . . . . .
C7 C 0.69051(19) 0.84654(18) 0.60346(15) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.6830(2) 0.9750(2) 0.53945(17) 0.0259(3) Uani 1 1 d . . . . .
H8 H 0.7145 0.9810 0.4593 0.031 Uiso 1 1 calc R . . . .
C9 C 0.6292(2) 1.0935(2) 0.59417(18) 0.0285(4) Uani 1 1 d . . . . .
H9 H 0.6216 1.1815 0.5511 0.034 Uiso 1 1 calc R . . . .
C10 C 0.5861(2) 1.08368(19) 0.71277(18) 0.0268(3) Uani 1 1 d . . . . .
H10 H 0.5512 1.1651 0.7519 0.032 Uiso 1 1 calc R . . . .
C11 C 0.5949(2) 0.95417(18) 0.77248(16) 0.0226(3) Uani 1 1 d . . . . .
H11 H 0.5650 0.9465 0.8530 0.027 Uiso 1 1 calc R . . . .
C12 C 0.76247(18) 0.66201(16) 0.90186(14) 0.0165(3) Uani 1 1 d . . . . .
C13 C 0.74463(18) 0.54679(17) 0.98013(14) 0.0174(3) Uani 1 1 d . . . . .
C14 C 0.84527(19) 0.52550(18) 1.09380(14) 0.0210(3) Uani 1 1 d . . . . .
H14 H 0.8280 0.4486 1.1465 0.025 Uiso 1 1 calc R . . . .
C15 C 0.9707(2) 0.61730(19) 1.12948(16) 0.0226(3) Uani 1 1 d . . . . .
H15 H 1.0402 0.6028 1.2063 0.027 Uiso 1 1 calc R . . . .
C16 C 0.99393(19) 0.73017(18) 1.05263(16) 0.0219(3) Uani 1 1 d . . . . .
H16 H 1.0808 0.7921 1.0756 0.026 Uiso 1 1 calc R . . . .
C17 C 0.88956(19) 0.75237(17) 0.94173(15) 0.0192(3) Uani 1 1 d . . . . .
H17 H 0.9051 0.8318 0.8912 0.023 Uiso 1 1 calc R . . . .
C18 C 0.46862(18) 0.63253(16) 0.77988(14) 0.0167(3) Uani 1 1 d . . . . .
C19 C 0.44240(19) 0.51214(18) 0.84894(14) 0.0184(3) Uani 1 1 d . . . . .
C20 C 0.2915(2) 0.4602(2) 0.85386(16) 0.0228(3) Uani 1 1 d . . . . .
H20 H 0.2782 0.3762 0.8992 0.027 Uiso 1 1 calc R . . . .
C21 C 0.1610(2) 0.5324(2) 0.79193(16) 0.0258(3) Uani 1 1 d . . . . .
H21 H 0.0579 0.4980 0.7945 0.031 Uiso 1 1 calc R . . . .
C22 C 0.1821(2) 0.65544(19) 0.72606(16) 0.0234(3) Uani 1 1 d . . . . .
H22 H 0.0933 0.7065 0.6849 0.028 Uiso 1 1 calc R . . . .
C23 C 0.33364(19) 0.70350(18) 0.72061(14) 0.0192(3) Uani 1 1 d . . . . .
H23 H 0.3461 0.7876 0.6750 0.023 Uiso 1 1 calc R . . . .
B1 B 0.6465(2) 0.67955(19) 0.76973(16) 0.0168(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C13 1.7742(16) . ?
S1 C19 1.7760(17) . ?
N1 C7 1.363(2) . ?
N1 C11 1.340(2) . ?
N1 B1 1.605(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.409(2) . ?
C1 B1 1.617(2) . ?
C2 C3 1.394(2) . ?
C3 C4 1.396(3) . ?
C4 C5 1.384(3) . ?
C5 C6 1.399(2) . ?
C6 C7 1.459(2) . ?
C7 C8 1.393(2) . ?
C8 C9 1.381(3) . ?
C9 C10 1.394(3) . ?
C10 C11 1.380(2) . ?
C12 C13 1.402(2) . ?
C12 C17 1.399(2) . ?
C12 B1 1.611(2) . ?
C13 C14 1.397(2) . ?
C14 C15 1.389(2) . ?
C15 C16 1.386(2) . ?
C16 C17 1.391(2) . ?
C18 C19 1.399(2) . ?
C18 C23 1.402(2) . ?
C18 B1 1.616(2) . ?
C19 C20 1.398(2) . ?
C20 C21 1.388(3) . ?
C21 C22 1.390(3) . ?
C22 C23 1.392(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 S1 C19 102.60(8) . . ?
C7 N1 B1 112.12(13) . . ?
C11 N1 C7 121.08(14) . . ?
C11 N1 B1 126.61(13) . . ?
C2 C1 C6 117.75(14) . . ?
C2 C1 B1 132.15(14) . . ?
C6 C1 B1 110.01(14) . . ?
C1 C2 C3 120.32(16) . . ?
C2 C3 C4 120.67(17) . . ?
C5 C4 C3 120.59(16) . . ?
C4 C5 C6 118.06(17) . . ?
C1 C6 C7 110.03(14) . . ?
C5 C6 C1 122.59(16) . . ?
C5 C6 C7 127.36(16) . . ?
N1 C7 C6 110.36(14) . . ?
N1 C7 C8 120.04(16) . . ?
C8 C7 C6 129.60(15) . . ?
C9 C8 C7 119.03(16) . . ?
C8 C9 C10 119.88(17) . . ?
C11 C10 C9 119.08(17) . . ?
N1 C11 C10 120.88(16) . . ?
C13 C12 B1 120.07(14) . . ?
C17 C12 C13 116.46(14) . . ?
C17 C12 B1 123.35(14) . . ?
C12 C13 S1 122.01(12) . . ?
C14 C13 S1 116.01(12) . . ?
C14 C13 C12 121.91(15) . . ?
C15 C14 C13 119.73(15) . . ?
C16 C15 C14 119.74(15) . . ?
C15 C16 C17 119.73(15) . . ?
C16 C17 C12 122.37(15) . . ?
C19 C18 C23 116.02(14) . . ?
C19 C18 B1 119.83(13) . . ?
C23 C18 B1 124.14(14) . . ?
C18 C19 S1 122.17(12) . . ?
C20 C19 S1 115.30(13) . . ?
C20 C19 C18 122.53(15) . . ?
C21 C20 C19 119.51(16) . . ?
C20 C21 C22 119.65(16) . . ?
C21 C22 C23 119.74(16) . . ?
C22 C23 C18 122.47(16) . . ?
N1 B1 C1 97.27(12) . . ?
N1 B1 C12 111.82(13) . . ?
N1 B1 C18 109.14(13) . . ?
C12 B1 C1 111.82(13) . . ?
C12 B1 C18 111.60(12) . . ?
C18 B1 C1 114.39(13) . . ?

_olex2_exptl_crystal_mounting_method 
'Mounted on MiTeGen Dual-Thickness MicroMounts in paraffin oil.'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AL41
_database_code_depnum_ccdc_archive 'CCDC 1830514'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_audit_creation_date             2017-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H17 B F2 N2'
_chemical_formula_sum            'C24 H17 B F2 N2'
_chemical_formula_weight         382.20
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      100(1)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0580(6)
_cell_length_b                   10.2042(7)
_cell_length_c                   10.5865(7)
_cell_angle_alpha                72.129(5)
_cell_angle_beta                 79.861(5)
_cell_angle_gamma                78.732(5)
_cell_volume                     906.25(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14347
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.20
_cell_measurement_theta_min      2.12
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.02380
_exptl_absorpt_correction_T_min  0.91777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'MULABS / PLATON Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. Spek, A.L. (2009). Acta Cryst. D65, 148-155.'
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13692
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.054
_diffrn_reflns_theta_min         2.311
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3983
_reflns_number_total             4820
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+0.6292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1264
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained planarity
 F1A, F2A, N1A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A, H4A,
 H8A, H9A, H10A
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
Uiso(F1A) = Uiso(F2A) = Uiso(N1A) = Uiso(C1A) = Uiso(C2A) = Uiso(C3A) =
Uiso(C4A) = Uiso(C5A) = Uiso(C6A) = Uiso(C7A) = Uiso(C8A) = Uiso(C9A) =
Uiso(C10A) = Uiso(C11A)
4. Same fragment restrains
{F1, F2, N1, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11} sigma for 1-2: 0.01,
1-3: 0.01
as
{F1A, F2A, N1A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A}
5. Others
 Sof(F1A)=Sof(F2A)=Sof(N1A)=Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C4A)=
 Sof(H4A)=Sof(C5A)=Sof(C6A)=Sof(C7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=
 Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(N1)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(C4)=Sof(H4)=
 Sof(C5)=Sof(C6)=Sof(C7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=
 Sof(C11)=Sof(H11)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22),
 C23(H23), C2(H2), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C2A(H2A),
 C4A(H4A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A)
6.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 1.01615(15) 0.53350(14) 0.22269(14) 0.0227(3) Uani 1 1 d . . . . .
C12 C 0.74352(17) 0.60511(16) 0.21856(15) 0.0202(3) Uani 1 1 d . . . . .
C13 C 0.87469(17) 0.50693(16) 0.20683(15) 0.0207(3) Uani 1 1 d . . . . .
C14 C 0.86393(19) 0.38210(17) 0.18195(16) 0.0244(3) Uani 1 1 d . . . . .
H14 H 0.9527 0.3161 0.1752 0.029 Uiso 1 1 calc R . . . .
C15 C 0.7262(2) 0.35395(18) 0.16717(18) 0.0293(4) Uani 1 1 d . . . . .
H15 H 0.7210 0.2699 0.1483 0.035 Uiso 1 1 calc R . . . .
C16 C 0.5952(2) 0.44792(19) 0.1797(2) 0.0322(4) Uani 1 1 d . . . . .
H16 H 0.4999 0.4287 0.1702 0.039 Uiso 1 1 calc R . . . .
C17 C 0.60552(19) 0.57123(18) 0.20651(18) 0.0269(3) Uani 1 1 d . . . . .
H17 H 0.5153 0.6345 0.2169 0.032 Uiso 1 1 calc R . . . .
C18 C 0.90371(17) 0.72001(16) 0.32384(14) 0.0195(3) Uani 1 1 d . . . . .
C19 C 1.02361(17) 0.61301(16) 0.30870(15) 0.0207(3) Uani 1 1 d . . . . .
C20 C 1.14880(18) 0.58582(17) 0.37948(16) 0.0250(3) Uani 1 1 d . . . . .
H20 H 1.2293 0.5132 0.3694 0.030 Uiso 1 1 calc R . . . .
C21 C 1.15563(19) 0.66393(19) 0.46373(16) 0.0268(3) Uani 1 1 d . . . . .
H21 H 1.2407 0.6444 0.5114 0.032 Uiso 1 1 calc R . . . .
C22 C 1.03877(19) 0.77112(19) 0.47935(16) 0.0273(3) Uani 1 1 d . . . . .
H22 H 1.0436 0.8254 0.5367 0.033 Uiso 1 1 calc R . . . .
C23 C 0.91490(18) 0.79719(17) 0.40937(15) 0.0235(3) Uani 1 1 d . . . . .
H23 H 0.8350 0.8701 0.4201 0.028 Uiso 1 1 calc R . . . .
C24 C 1.15322(19) 0.44441(18) 0.18642(18) 0.0290(4) Uani 1 1 d . . . . .
H24A H 1.1671 0.3579 0.2591 0.044 Uiso 1 1 calc GR . . . .
H24B H 1.2409 0.4928 0.1713 0.044 Uiso 1 1 calc GR . . . .
H24C H 1.1439 0.4226 0.1045 0.044 Uiso 1 1 calc GR . . . .
B1 B 0.76182(19) 0.74833(17) 0.24243(16) 0.0187(3) Uani 1 1 d . . . . .
F1 F 0.31108(12) 0.88699(11) 0.56045(10) 0.0267(3) Uani 0.931(3) 1 d D . P A 1
F2 F 0.42284(12) 1.18668(11) 0.13286(11) 0.0284(3) Uani 0.931(3) 1 d D . P A 1
N1 N 0.79348(17) 0.86233(15) 0.09692(15) 0.0175(3) Uani 0.931(3) 1 d D . P A 1
C1 C 0.6118(2) 0.8392(2) 0.29628(18) 0.0182(3) Uani 0.931(3) 1 d D . P A 1
C2 C 0.5196(2) 0.8110(2) 0.41894(18) 0.0206(4) Uani 0.931(3) 1 d D . P A 1
H2 H 0.5389 0.7250 0.4857 0.025 Uiso 0.931(3) 1 calc R . P A 1
C3 C 0.3995(2) 0.9118(2) 0.44045(19) 0.0220(4) Uani 0.931(3) 1 d D . P A 1
C4 C 0.3632(2) 1.0385(2) 0.3472(2) 0.0224(4) Uani 0.931(3) 1 d D . P A 1
H4 H 0.2786 1.1044 0.3653 0.027 Uiso 0.931(3) 1 calc R . P A 1
C5 C 0.4558(2) 1.0642(2) 0.2272(2) 0.0206(4) Uani 0.931(3) 1 d D . P A 1
C6 C 0.5791(2) 0.96823(19) 0.20024(18) 0.0184(3) Uani 0.931(3) 1 d D . P A 1
C7 C 0.6895(2) 0.97979(18) 0.08008(17) 0.0180(3) Uani 0.931(3) 1 d D . P A 1
C8 C 0.6992(2) 1.08739(18) -0.03812(18) 0.0209(4) Uani 0.931(3) 1 d D . P A 1
H8 H 0.6270 1.1699 -0.0494 0.025 Uiso 0.931(3) 1 calc R . P A 1
C9 C 0.8158(2) 1.07253(19) -0.13918(18) 0.0220(4) Uani 0.931(3) 1 d D . P A 1
H9 H 0.8238 1.1446 -0.2209 0.026 Uiso 0.931(3) 1 calc R . P A 1
C10 C 0.9213(2) 0.9507(2) -0.11972(18) 0.0220(4) Uani 0.931(3) 1 d D . P A 1
H10 H 1.0018 0.9391 -0.1880 0.026 Uiso 0.931(3) 1 calc R . P A 1
C11 C 0.9073(2) 0.84747(19) -0.00036(18) 0.0197(3) Uani 0.931(3) 1 d D . P A 1
H11 H 0.9793 0.7646 0.0134 0.024 Uiso 0.931(3) 1 calc R . P A 1
F1A F 1.0209(16) 0.9487(17) -0.2257(15) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
F2A F 0.5957(16) 1.2012(15) -0.0392(15) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
N1A N 0.613(3) 0.836(2) 0.2953(17) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
C1A C 0.795(2) 0.8502(17) 0.0972(17) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
C2A C 0.9085(19) 0.8419(17) -0.0092(18) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
H2A H 0.9816 0.7604 -0.0046 0.049 Uiso 0.069(3) 1 calc R . P A 2
C3A C 0.9113(16) 0.9554(18) -0.1214(16) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
C4A C 0.8088(16) 1.0774(16) -0.1354(15) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
H4A H 0.8147 1.1532 -0.2142 0.049 Uiso 0.069(3) 1 calc R . P A 2
C5A C 0.6982(16) 1.0833(15) -0.0292(16) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
C6A C 0.6892(18) 0.9731(16) 0.0859(15) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
C7A C 0.580(2) 0.962(2) 0.2066(17) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
C8A C 0.458(2) 1.058(3) 0.238(2) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
H8A H 0.4350 1.1468 0.1754 0.049 Uiso 0.069(3) 1 calc R . P A 2
C9A C 0.370(3) 1.023(4) 0.361(3) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
H9A H 0.2859 1.0870 0.3837 0.049 Uiso 0.069(3) 1 calc R . P A 2
C10A C 0.406(3) 0.892(4) 0.450(2) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
H10A H 0.3464 0.8664 0.5349 0.049 Uiso 0.069(3) 1 calc R . P A 2
C11A C 0.528(3) 0.801(3) 0.4149(19) 0.041(3) Uiso 0.069(3) 1 d D . P A 2
H11A H 0.5522 0.7119 0.4758 0.049 Uiso 0.069(3) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C13 1.408(2) . ?
N2 C19 1.410(2) . ?
N2 C24 1.4563(19) . ?
C12 C13 1.411(2) . ?
C12 C17 1.397(2) . ?
C12 B1 1.601(2) . ?
C13 C14 1.402(2) . ?
C14 C15 1.379(2) . ?
C15 C16 1.387(2) . ?
C16 C17 1.395(2) . ?
C18 C19 1.407(2) . ?
C18 C23 1.397(2) . ?
C18 B1 1.603(2) . ?
C19 C20 1.405(2) . ?
C20 C21 1.382(2) . ?
C21 C22 1.393(2) . ?
C22 C23 1.391(2) . ?
B1 N1 1.638(2) . ?
B1 C1 1.610(3) . ?
B1 N1A 1.58(2) . ?
B1 C1A 1.585(17) . ?
F1 C3 1.358(2) . ?
F2 C5 1.357(2) . ?
N1 C7 1.357(2) . ?
N1 C11 1.345(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.409(2) . ?
C2 C3 1.383(2) . ?
C3 C4 1.385(2) . ?
C4 C5 1.376(2) . ?
C5 C6 1.386(2) . ?
C6 C7 1.462(2) . ?
C7 C8 1.391(2) . ?
C8 C9 1.386(2) . ?
C9 C10 1.396(2) . ?
C10 C11 1.379(2) . ?
F1A C3A 1.358(8) . ?
F2A C5A 1.357(8) . ?
N1A C7A 1.357(8) . ?
N1A C11A 1.345(9) . ?
C1A C2A 1.396(8) . ?
C1A C6A 1.409(8) . ?
C2A C3A 1.382(9) . ?
C3A C4A 1.385(8) . ?
C4A C5A 1.375(8) . ?
C5A C6A 1.384(8) . ?
C6A C7A 1.462(7) . ?
C7A C8A 1.391(8) . ?
C8A C9A 1.385(9) . ?
C9A C10A 1.395(9) . ?
C10A C11A 1.376(9) . ?

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
C13 N2 C19 119.94(12) . . ?
C13 N2 C24 118.85(13) . . ?
C19 N2 C24 118.30(13) . . ?
C13 C12 B1 118.45(13) . . ?
C17 C12 C13 117.37(14) . . ?
C17 C12 B1 124.18(14) . . ?
N2 C13 C12 119.80(14) . . ?
C14 C13 N2 120.05(14) . . ?
C14 C13 C12 120.14(15) . . ?
C15 C14 C13 120.81(15) . . ?
C14 C15 C16 120.25(16) . . ?
C15 C16 C17 118.94(16) . . ?
C16 C17 C12 122.46(15) . . ?
C19 C18 B1 118.94(13) . . ?
C23 C18 C19 117.95(14) . . ?
C23 C18 B1 123.11(13) . . ?
C18 C19 N2 119.38(14) . . ?
C20 C19 N2 120.65(14) . . ?
C20 C19 C18 119.97(15) . . ?
C21 C20 C19 120.46(15) . . ?
C20 C21 C22 120.52(15) . . ?
C23 C22 C21 118.74(16) . . ?
C22 C23 C18 122.36(15) . . ?
C12 B1 C18 108.46(12) . . ?
C12 B1 N1 108.80(12) . . ?
C12 B1 C1 117.75(14) . . ?
C18 B1 N1 109.58(12) . . ?
C18 B1 C1 115.13(13) . . ?
C1 B1 N1 96.18(12) . . ?
N1A B1 C12 116.8(8) . . ?
N1A B1 C18 115.8(7) . . ?
N1A B1 C1A 99.3(10) . . ?
C1A B1 C12 105.1(6) . . ?
C1A B1 C18 110.4(6) . . ?
C7 N1 B1 112.98(13) . . ?
C11 N1 B1 126.30(13) . . ?
C11 N1 C7 120.72(14) . . ?
C2 C1 B1 130.44(15) . . ?
C2 C1 C6 119.01(15) . . ?
C6 C1 B1 110.50(14) . . ?
C3 C2 C1 118.08(16) . . ?
F1 C3 C2 118.68(17) . . ?
F1 C3 C4 117.12(17) . . ?
C2 C3 C4 124.19(16) . . ?
C5 C4 C3 116.71(15) . . ?
F2 C5 C4 118.38(15) . . ?
F2 C5 C6 119.75(16) . . ?
C4 C5 C6 121.86(16) . . ?
C1 C6 C7 111.05(14) . . ?
C5 C6 C1 120.13(15) . . ?
C5 C6 C7 128.82(16) . . ?
N1 C7 C6 109.29(14) . . ?
N1 C7 C8 120.52(15) . . ?
C8 C7 C6 130.19(15) . . ?
C9 C8 C7 119.11(15) . . ?
C8 C9 C10 119.36(16) . . ?
C11 C10 C9 119.33(15) . . ?
N1 C11 C10 120.96(15) . . ?
C7A N1A B1 111.7(8) . . ?
C11A N1A B1 127.5(10) . . ?
C11A N1A C7A 120.6(7) . . ?
C2A C1A B1 132.7(10) . . ?
C2A C1A C6A 118.9(7) . . ?
C6A C1A B1 108.3(9) . . ?
C3A C2A C1A 118.1(7) . . ?
F1A C3A C2A 118.7(8) . . ?
F1A C3A C4A 117.0(8) . . ?
C2A C3A C4A 124.3(7) . . ?
C5A C4A C3A 116.6(7) . . ?
F2A C5A C4A 118.3(8) . . ?
F2A C5A C6A 119.8(8) . . ?
C4A C5A C6A 121.9(7) . . ?
C1A C6A C7A 111.0(6) . . ?
C5A C6A C1A 120.2(6) . . ?
C5A C6A C7A 128.8(7) . . ?
N1A C7A C6A 109.3(6) . . ?
N1A C7A C8A 120.6(6) . . ?
C8A C7A C6A 130.1(8) . . ?
C9A C8A C7A 119.1(8) . . ?
C8A C9A C10A 119.3(7) . . ?
C11A C10A C9A 119.4(8) . . ?
N1A C11A C10A 121.0(8) . . ?

_olex2_exptl_crystal_mounting_method 
'Mounted on MiTeGen Dual-Thickness MicroMounts in paraffin oil.'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AL38
_database_code_depnum_ccdc_archive 'CCDC 1830513'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_audit_creation_date             2017-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H19 B N2'
_chemical_formula_sum            'C24 H19 B N2'
_chemical_formula_weight         346.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'
_chemical_absolute_configuration unk
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      100(1)
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'

_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.
;

_cell_length_a                   10.4501(8)
_cell_length_b                   24.7509(16)
_cell_length_c                   8.0062(6)
_cell_angle_alpha                90
_cell_angle_beta                 120.520(5)
_cell_angle_gamma                90
_cell_volume                     1783.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13436
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      29.83
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.06906
_exptl_absorpt_correction_T_min  0.92047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'MULABS / PLATON Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. Spek, A.L. (2009). Acta Cryst. D65, 148-155.'
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12068
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.556
_diffrn_reflns_theta_min         2.781
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_reflns_Friedel_coverage         0.988
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3695
_reflns_number_total             4527
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1491 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4527
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0966
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5978(2) 0.69609(9) 0.3652(3) 0.0306(5) Uani 1 1 d . . . . .
N2 N 0.4696(2) 0.57056(9) 0.1078(3) 0.0295(5) Uani 1 1 d . . . . .
C1 C 0.6773(2) 0.65445(10) 0.6749(3) 0.0250(5) Uani 1 1 d . . . . .
C2 C 0.7202(3) 0.62463(11) 0.8428(4) 0.0345(6) Uani 1 1 d . . . . .
H2 H 0.7007 0.5869 0.8335 0.041 Uiso 1 1 calc R . . . .
C3 C 0.7908(3) 0.64926(13) 1.0230(4) 0.0403(7) Uani 1 1 d . . . . .
H3 H 0.8195 0.6284 1.1362 0.048 Uiso 1 1 calc R . . . .
C4 C 0.8197(3) 0.70410(13) 1.0385(4) 0.0429(7) Uani 1 1 d . . . . .
H4 H 0.8684 0.7207 1.1627 0.051 Uiso 1 1 calc R . . . .
C5 C 0.7783(3) 0.73501(12) 0.8752(4) 0.0366(6) Uani 1 1 d . . . . .
H5 H 0.7980 0.7727 0.8854 0.044 Uiso 1 1 calc R . . . .
C6 C 0.7073(3) 0.70959(10) 0.6957(4) 0.0282(5) Uani 1 1 d . . . . .
C7 C 0.6581(3) 0.73441(10) 0.5070(4) 0.0276(5) Uani 1 1 d . . . . .
C8 C 0.6679(3) 0.78824(11) 0.4648(4) 0.0339(6) Uani 1 1 d . . . . .
H8 H 0.7081 0.8147 0.5646 0.041 Uiso 1 1 calc R . . . .
C9 C 0.6178(3) 0.80225(12) 0.2753(5) 0.0402(7) Uani 1 1 d . . . . .
H9 H 0.6246 0.8387 0.2432 0.048 Uiso 1 1 calc R . . . .
C10 C 0.5576(4) 0.76336(14) 0.1309(5) 0.0450(8) Uani 1 1 d . . . . .
H10 H 0.5235 0.7730 0.0000 0.054 Uiso 1 1 calc R . . . .
C11 C 0.5476(3) 0.71037(12) 0.1790(4) 0.0372(6) Uani 1 1 d . . . . .
H11 H 0.5050 0.6838 0.0799 0.045 Uiso 1 1 calc R . . . .
C12 C 0.4356(3) 0.61248(10) 0.3577(4) 0.0262(5) Uani 1 1 d . . . . .
C13 C 0.3776(3) 0.58267(10) 0.1836(4) 0.0278(5) Uani 1 1 d . . . . .
C14 C 0.2292(3) 0.56512(10) 0.0889(4) 0.0325(6) Uani 1 1 d . . . . .
H14 H 0.1898 0.5455 -0.0291 0.039 Uiso 1 1 calc R . . . .
C15 C 0.1398(3) 0.57630(11) 0.1669(4) 0.0364(6) Uani 1 1 d . . . . .
H15 H 0.0389 0.5650 0.1002 0.044 Uiso 1 1 calc R . . . .
C16 C 0.1967(3) 0.60372(11) 0.3409(4) 0.0348(6) Uani 1 1 d . . . . .
H16 H 0.1362 0.6108 0.3955 0.042 Uiso 1 1 calc R . . . .
C17 C 0.3433(3) 0.62064(10) 0.4342(4) 0.0299(6) Uani 1 1 d . . . . .
H17 H 0.3826 0.6386 0.5555 0.036 Uiso 1 1 calc R . . . .
C18 C 0.6963(3) 0.59558(10) 0.4049(4) 0.0258(5) Uani 1 1 d . . . . .
C19 C 0.6246(3) 0.56426(10) 0.2341(4) 0.0268(5) Uani 1 1 d . . . . .
C20 C 0.7060(3) 0.52803(10) 0.1907(4) 0.0314(5) Uani 1 1 d . . . . .
H20 H 0.6570 0.5066 0.0768 0.038 Uiso 1 1 calc R . . . .
C21 C 0.8578(3) 0.52333(11) 0.3131(4) 0.0327(6) Uani 1 1 d . . . . .
H21 H 0.9126 0.4990 0.2816 0.039 Uiso 1 1 calc R . . . .
C22 C 0.9304(3) 0.55368(11) 0.4805(4) 0.0310(6) Uani 1 1 d . . . . .
H22 H 1.0349 0.5505 0.5636 0.037 Uiso 1 1 calc R . . . .
C23 C 0.8496(3) 0.58867(10) 0.5257(4) 0.0266(5) Uani 1 1 d . . . . .
H23 H 0.8998 0.6087 0.6430 0.032 Uiso 1 1 calc R . . . .
C24 C 0.4027(3) 0.54610(13) -0.0837(4) 0.0400(7) Uani 1 1 d . . . . .
H24A H 0.4704 0.5498 -0.1340 0.060 Uiso 1 1 calc GR . . . .
H24B H 0.3087 0.5643 -0.1714 0.060 Uiso 1 1 calc GR . . . .
H24C H 0.3839 0.5077 -0.0749 0.060 Uiso 1 1 calc GR . . . .
B1 B 0.6004(3) 0.63603(12) 0.4527(4) 0.0290(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.364(3) . ?
N1 C11 1.352(4) . ?
N1 B1 1.637(4) . ?
N2 C13 1.405(3) . ?
N2 C19 1.417(3) . ?
N2 C24 1.456(3) . ?
C1 C2 1.393(4) . ?
C1 C6 1.391(3) . ?
C1 B1 1.602(4) . ?
C2 C3 1.384(4) . ?
C3 C4 1.382(4) . ?
C4 C5 1.381(4) . ?
C5 C6 1.388(4) . ?
C6 C7 1.461(4) . ?
C7 C8 1.391(4) . ?
C8 C9 1.375(4) . ?
C9 C10 1.385(5) . ?
C10 C11 1.386(5) . ?
C12 C13 1.413(4) . ?
C12 C17 1.396(4) . ?
C12 B1 1.599(4) . ?
C13 C14 1.405(3) . ?
C14 C15 1.390(4) . ?
C15 C16 1.383(4) . ?
C16 C17 1.385(4) . ?
C18 C19 1.411(3) . ?
C18 C23 1.399(3) . ?
C18 B1 1.594(4) . ?
C19 C20 1.396(4) . ?
C20 C21 1.382(4) . ?
C21 C22 1.379(4) . ?
C22 C23 1.381(4) . ?

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
C7 N1 B1 112.0(2) . . ?
C11 N1 C7 119.5(2) . . ?
C11 N1 B1 128.5(2) . . ?
C13 N2 C19 120.0(2) . . ?
C13 N2 C24 118.4(2) . . ?
C19 N2 C24 118.0(2) . . ?
C2 C1 B1 130.9(2) . . ?
C6 C1 C2 117.5(2) . . ?
C6 C1 B1 111.6(2) . . ?
C3 C2 C1 120.8(3) . . ?
C4 C3 C2 120.2(3) . . ?
C5 C4 C3 120.6(3) . . ?
C4 C5 C6 118.3(3) . . ?
C1 C6 C7 110.4(2) . . ?
C5 C6 C1 122.5(2) . . ?
C5 C6 C7 127.0(2) . . ?
N1 C7 C6 109.9(2) . . ?
N1 C7 C8 121.6(2) . . ?
C8 C7 C6 128.5(2) . . ?
C9 C8 C7 118.4(3) . . ?
C8 C9 C10 120.2(3) . . ?
C9 C10 C11 119.5(3) . . ?
N1 C11 C10 120.8(3) . . ?
C13 C12 B1 118.6(2) . . ?
C17 C12 C13 117.6(2) . . ?
C17 C12 B1 123.8(2) . . ?
N2 C13 C12 119.5(2) . . ?
C14 C13 N2 120.7(2) . . ?
C14 C13 C12 119.8(2) . . ?
C15 C14 C13 120.4(3) . . ?
C16 C15 C14 120.4(2) . . ?
C15 C16 C17 119.0(3) . . ?
C16 C17 C12 122.7(3) . . ?
C19 C18 B1 119.2(2) . . ?
C23 C18 C19 117.4(2) . . ?
C23 C18 B1 123.3(2) . . ?
C18 C19 N2 118.9(2) . . ?
C20 C19 N2 120.9(2) . . ?
C20 C19 C18 120.2(2) . . ?
C21 C20 C19 120.2(2) . . ?
C22 C21 C20 120.7(2) . . ?
C21 C22 C23 119.2(2) . . ?
C22 C23 C18 122.3(2) . . ?
C1 B1 N1 96.15(19) . . ?
C12 B1 N1 110.3(2) . . ?
C12 B1 C1 116.3(2) . . ?
C18 B1 N1 110.1(2) . . ?
C18 B1 C1 115.1(2) . . ?
C18 B1 C12 108.3(2) . . ?

_olex2_exptl_crystal_mounting_method 
'Mounted on MiTeGen Dual-Thickness MicroMounts in paraffin oil.'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AL46
_database_code_depnum_ccdc_archive 'CCDC 1830515'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_audit_creation_date             2018-02-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C41 H45 B N2, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C41.50 H46 B Cl N2'
_chemical_formula_weight         619.06
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      100(1)
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'

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

_cell_length_a                   7.7660(4)
_cell_length_b                   13.7779(7)
_cell_length_c                   17.7144(9)
_cell_angle_alpha                70.971(4)
_cell_angle_beta                 82.959(4)
_cell_angle_gamma                89.145(4)
_cell_volume                     1777.70(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24062
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.98649
_exptl_absorpt_correction_T_min  0.91780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'MULABS / PLATON Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. Spek, A.L. (2009). Acta Cryst. D65, 148-155.'
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             662
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27942
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.091
_diffrn_reflns_theta_min         2.281
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5589
_reflns_number_total             7774
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         7774
_refine_ls_number_restraints     262
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0623P)²+0.2643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1241
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N1, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N1A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(C1A)
Uanis(C1) = Uanis(N1A)
4. Rigid body (RIGU) restrains
 N1, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{N1, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11} sigma for 1-2: 0.02, 1-3:
0.04
as
{N1A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A}
6. Others
 Sof(N1A)=Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=
 Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=1-FVAR(1)
 Sof(N1)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=
 Sof(H5)=Sof(C6)=Sof(C7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=
 Sof(C11)=Sof(H11)=FVAR(1)
 Fixed Sof: Cl1(0.5) Cl2(0.5) C42(0.5) H42A(0.5) H42B(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C42(H42A,H42B)
7.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C20(H20), C21(H21), C23(H23), C25(H25),
 C26(H26), C28(H28), C29(H29), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9),
 C10(H10), C11(H11), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C8A(H8A), C9A(H9A),
  C10A(H10A), C11A(H11A)
7.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C35(H35A,H35B,
 H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C39(H39A,H39B,H39C), C40(H40A,
 H40B,H40C), C41(H41A,H41B,H41C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 1.03074(16) 0.70002(10) 0.30320(8) 0.0260(3) Uani 1 1 d . . . . .
C12 C 0.93070(18) 0.63055(11) 0.20475(9) 0.0220(3) Uani 1 1 d . . . . .
C13 C 1.02600(18) 0.62036(11) 0.26922(9) 0.0229(3) Uani 1 1 d . . . . .
C14 C 1.11825(19) 0.53075(12) 0.29957(10) 0.0272(3) Uani 1 1 d . . . . .
H14 H 1.1837 0.5238 0.3429 0.033 Uiso 1 1 calc R . . . .
C15 C 1.1149(2) 0.45212(12) 0.26691(10) 0.0285(3) Uani 1 1 d . . . . .
H15 H 1.1787 0.3921 0.2885 0.034 Uiso 1 1 calc R . . . .
C16 C 1.0210(2) 0.45842(12) 0.20355(10) 0.0265(3) Uani 1 1 d . . . . .
C17 C 0.93148(19) 0.54889(11) 0.17430(9) 0.0241(3) Uani 1 1 d . . . . .
H17 H 0.8668 0.5554 0.1308 0.029 Uiso 1 1 calc R . . . .
C18 C 0.79645(18) 0.79356(11) 0.23162(9) 0.0225(3) Uani 1 1 d . . . . .
C19 C 0.90599(19) 0.77767(11) 0.29181(9) 0.0243(3) Uani 1 1 d . . . . .
C20 C 0.8926(2) 0.84120(13) 0.33999(11) 0.0321(4) Uani 1 1 d . . . . .
H20 H 0.9712 0.8340 0.3785 0.039 Uiso 1 1 calc R . . . .
C21 C 0.7658(2) 0.91434(13) 0.33181(11) 0.0331(4) Uani 1 1 d . . . . .
H21 H 0.7603 0.9569 0.3648 0.040 Uiso 1 1 calc R . . . .
C22 C 0.6460(2) 0.92793(12) 0.27703(10) 0.0269(3) Uani 1 1 d . . . . .
C23 C 0.66790(19) 0.86732(11) 0.22713(9) 0.0239(3) Uani 1 1 d . . . . .
H23 H 0.5911 0.8765 0.1877 0.029 Uiso 1 1 calc R . . . .
C24 C 1.13364(19) 0.68440(12) 0.36830(9) 0.0249(3) Uani 1 1 d . . . . .
C25 C 1.3059(2) 0.71629(12) 0.35229(10) 0.0282(3) Uani 1 1 d . . . . .
H25 H 1.3569 0.7473 0.2982 0.034 Uiso 1 1 calc R . . . .
C26 C 1.4050(2) 0.70326(12) 0.41476(10) 0.0289(3) Uani 1 1 d . . . . .
H26 H 1.5234 0.7254 0.4026 0.035 Uiso 1 1 calc R . . . .
C27 C 1.33470(19) 0.65845(11) 0.49502(9) 0.0249(3) Uani 1 1 d . . . . .
C28 C 1.1614(2) 0.62457(13) 0.50929(10) 0.0308(4) Uani 1 1 d . . . . .
H28 H 1.1099 0.5924 0.5631 0.037 Uiso 1 1 calc R . . . .
C29 C 1.0631(2) 0.63665(14) 0.44717(10) 0.0318(4) Uani 1 1 d . . . . .
H29 H 0.9460 0.6120 0.4587 0.038 Uiso 1 1 calc R . . . .
C30 C 1.0215(2) 0.37469(13) 0.16415(11) 0.0361(4) Uani 1 1 d . . . . .
C31 C 0.8390(3) 0.35572(14) 0.14664(13) 0.0449(5) Uani 1 1 d . . . . .
H31A H 0.7593 0.3362 0.1968 0.067 Uiso 1 1 calc GR . . . .
H31B H 0.8416 0.3002 0.1233 0.067 Uiso 1 1 calc GR . . . .
H31C H 0.7994 0.4186 0.1086 0.067 Uiso 1 1 calc GR . . . .
C32 C 1.1428(3) 0.41118(19) 0.08463(14) 0.0577(6) Uani 1 1 d . . . . .
H32A H 1.1064 0.4782 0.0512 0.087 Uiso 1 1 calc GR . . . .
H32B H 1.1377 0.3614 0.0561 0.087 Uiso 1 1 calc GR . . . .
H32C H 1.2620 0.4172 0.0958 0.087 Uiso 1 1 calc GR . . . .
C33 C 1.0839(4) 0.27260(16) 0.21823(15) 0.0644(7) Uani 1 1 d . . . . .
H33A H 1.2063 0.2801 0.2243 0.097 Uiso 1 1 calc GR . . . .
H33B H 1.0710 0.2191 0.1938 0.097 Uiso 1 1 calc GR . . . .
H33C H 1.0144 0.2533 0.2712 0.097 Uiso 1 1 calc GR . . . .
C34 C 0.5048(2) 1.00827(13) 0.27239(11) 0.0338(4) Uani 1 1 d . . . . .
C35 C 0.5905(3) 1.11611(14) 0.24081(13) 0.0474(5) Uani 1 1 d . . . . .
H35A H 0.6751 1.1211 0.2762 0.071 Uiso 1 1 calc GR . . . .
H35B H 0.5015 1.1675 0.2398 0.071 Uiso 1 1 calc GR . . . .
H35C H 0.6496 1.1285 0.1862 0.071 Uiso 1 1 calc GR . . . .
C36 C 0.3723(2) 1.00206(15) 0.21713(12) 0.0429(5) Uani 1 1 d . . . . .
H36A H 0.4308 1.0158 0.1623 0.064 Uiso 1 1 calc GR . . . .
H36B H 0.2832 1.0532 0.2172 0.064 Uiso 1 1 calc GR . . . .
H36C H 0.3178 0.9332 0.2364 0.064 Uiso 1 1 calc GR . . . .
C37 C 0.4057(3) 0.99181(15) 0.35641(12) 0.0442(5) Uani 1 1 d . . . . .
H37A H 0.3497 0.9234 0.3769 0.066 Uiso 1 1 calc GR . . . .
H37B H 0.3171 1.0440 0.3529 0.066 Uiso 1 1 calc GR . . . .
H37C H 0.4869 0.9975 0.3930 0.066 Uiso 1 1 calc GR . . . .
C38 C 1.4390(2) 0.65004(13) 0.56476(10) 0.0291(3) Uani 1 1 d . . . . .
C39 C 1.3960(4) 0.7410(2) 0.59339(17) 0.0754(9) Uani 1 1 d . . . . .
H39A H 1.4254 0.8049 0.5488 0.113 Uiso 1 1 calc GR . . . .
H39B H 1.4631 0.7382 0.6374 0.113 Uiso 1 1 calc GR . . . .
H39C H 1.2718 0.7388 0.6125 0.113 Uiso 1 1 calc GR . . . .
C40 C 1.3953(3) 0.55062(18) 0.63394(12) 0.0541(6) Uani 1 1 d . . . . .
H40A H 1.2724 0.5491 0.6551 0.081 Uiso 1 1 calc GR . . . .
H40B H 1.4670 0.5465 0.6767 0.081 Uiso 1 1 calc GR . . . .
H40C H 1.4184 0.4921 0.6146 0.081 Uiso 1 1 calc GR . . . .
C41 C 1.6337(2) 0.6497(2) 0.53823(13) 0.0557(6) Uani 1 1 d . . . . .
H41A H 1.6588 0.5936 0.5163 0.084 Uiso 1 1 calc GR . . . .
H41B H 1.6971 0.6401 0.5846 0.084 Uiso 1 1 calc GR . . . .
H41C H 1.6701 0.7154 0.4968 0.084 Uiso 1 1 calc GR . . . .
B1 B 0.8300(2) 0.73394(13) 0.16752(11) 0.0242(4) Uani 1 1 d . . . . .
N1 N 0.9465(16) 0.8048(13) 0.0888(6) 0.0250(9) Uani 0.649(12) 1 d D U P A 1
C1 C 0.663(2) 0.7210(15) 0.1242(9) 0.0221(12) Uani 0.649(12) 1 d D U P A 1
C2 C 0.5076(14) 0.6617(12) 0.1532(6) 0.0286(16) Uani 0.649(12) 1 d D U P A 1
H2 H 0.4799 0.6266 0.2093 0.034 Uiso 0.649(12) 1 calc R . P A 1
C3 C 0.3950(11) 0.6546(7) 0.0999(5) 0.0318(14) Uani 0.649(12) 1 d D U P A 1
H3 H 0.2901 0.6150 0.1197 0.038 Uiso 0.649(12) 1 calc R . P A 1
C4 C 0.4354(11) 0.7051(7) 0.0179(4) 0.0341(14) Uani 0.649(12) 1 d D U P A 1
H4 H 0.3575 0.6999 -0.0181 0.041 Uiso 0.649(12) 1 calc R . P A 1
C5 C 0.5884(11) 0.7630(8) -0.0121(5) 0.0325(14) Uani 0.649(12) 1 d D U P A 1
H5 H 0.6144 0.7982 -0.0682 0.039 Uiso 0.649(12) 1 calc R . P A 1
C6 C 0.7028(15) 0.7689(12) 0.0406(6) 0.0237(13) Uani 0.649(12) 1 d D U P A 1
C7 C 0.8743(12) 0.8202(11) 0.0204(6) 0.0260(13) Uani 0.649(12) 1 d D U P A 1
C8 C 0.9562(11) 0.8821(8) -0.0544(5) 0.0371(15) Uani 0.649(12) 1 d D U P A 1
H8 H 0.9029 0.8940 -0.1020 0.044 Uiso 0.649(12) 1 calc R . P A 1
C9 C 1.1174(10) 0.9255(5) -0.0567(4) 0.0398(16) Uani 0.649(12) 1 d D U P A 1
H9 H 1.1769 0.9679 -0.1064 0.048 Uiso 0.649(12) 1 calc R . P A 1
C10 C 1.1907(9) 0.9070(6) 0.0134(4) 0.0383(13) Uani 0.649(12) 1 d D U P A 1
H10 H 1.3021 0.9354 0.0121 0.046 Uiso 0.649(12) 1 calc R . P A 1
C11 C 1.1015(11) 0.8466(7) 0.0858(5) 0.0318(13) Uani 0.649(12) 1 d D U P A 1
H11 H 1.1519 0.8349 0.1341 0.038 Uiso 0.649(12) 1 calc R . P A 1
Cl1 Cl -0.0206(2) 1.07738(14) 0.47563(11) 0.0779(4) Uani 0.5 1 d . . P B -1
N1A N 0.674(3) 0.714(2) 0.1257(14) 0.0221(12) Uani 0.351(12) 1 d D U P A 2
C1A C 0.943(4) 0.812(3) 0.0791(15) 0.0250(9) Uani 0.351(12) 1 d D U P A 2
C2A C 1.110(2) 0.8597(14) 0.0634(8) 0.029(2) Uani 0.351(12) 1 d D U P A 2
H2A H 1.1784 0.8524 0.1059 0.035 Uiso 0.351(12) 1 calc R . P A 2
C3A C 1.1729(15) 0.9174(9) -0.0155(7) 0.032(2) Uani 0.351(12) 1 d D U P A 2
H3A H 1.2843 0.9504 -0.0272 0.038 Uiso 0.351(12) 1 calc R . P A 2
C4A C 1.0727(16) 0.9267(12) -0.0766(8) 0.032(2) Uani 0.351(12) 1 d D U P A 2
H4A H 1.1146 0.9678 -0.1300 0.038 Uiso 0.351(12) 1 calc R . P A 2
C5A C 0.9121(18) 0.8770(15) -0.0613(9) 0.029(2) Uani 0.351(12) 1 d D U P A 2
H5A H 0.8491 0.8803 -0.1047 0.035 Uiso 0.351(12) 1 calc R . P A 2
C6A C 0.842(2) 0.822(2) 0.0171(11) 0.022(2) Uani 0.351(12) 1 d D U P A 2
C7A C 0.680(3) 0.762(3) 0.0449(12) 0.025(3) Uani 0.351(12) 1 d D U P A 2
C8A C 0.552(2) 0.7469(15) -0.0007(9) 0.025(2) Uani 0.351(12) 1 d D U P A 2
H8A H 0.5621 0.7775 -0.0575 0.030 Uiso 0.351(12) 1 calc R . P A 2
C9A C 0.4115(16) 0.6855(11) 0.0424(8) 0.028(2) Uani 0.351(12) 1 d D U P A 2
H9A H 0.3218 0.6725 0.0147 0.033 Uiso 0.351(12) 1 calc R . P A 2
C10A C 0.398(2) 0.6425(14) 0.1246(7) 0.028(2) Uani 0.351(12) 1 d D U P A 2
H10A H 0.2991 0.6017 0.1538 0.034 Uiso 0.351(12) 1 calc R . P A 2
C11A C 0.531(3) 0.659(2) 0.1642(11) 0.025(2) Uani 0.351(12) 1 d D U P A 2
H11A H 0.5191 0.6312 0.2212 0.030 Uiso 0.351(12) 1 calc R . P A 2
Cl2 Cl -0.08313(18) 0.85716(11) 0.54059(8) 0.0623(3) Uani 0.5 1 d . . P B -1
C42 C 0.0393(8) 0.9635(7) 0.5429(4) 0.081(2) Uani 0.5 1 d . . P B -1
H42A H 0.0218 0.9680 0.5980 0.097 Uiso 0.5 1 calc R . P B -1
H42B H 0.1642 0.9529 0.5296 0.097 Uiso 0.5 1 calc R . P B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C13 1.4163(18) . ?
N2 C19 1.4142(19) . ?
N2 C24 1.4401(19) . ?
C12 C13 1.404(2) . ?
C12 C17 1.397(2) . ?
C12 B1 1.599(2) . ?
C13 C14 1.401(2) . ?
C14 C15 1.386(2) . ?
C15 C16 1.391(2) . ?
C16 C17 1.395(2) . ?
C16 C30 1.530(2) . ?
C18 C19 1.405(2) . ?
C18 C23 1.404(2) . ?
C18 B1 1.600(2) . ?
C19 C20 1.403(2) . ?
C20 C21 1.385(2) . ?
C21 C22 1.393(2) . ?
C22 C23 1.396(2) . ?
C22 C34 1.536(2) . ?
C24 C25 1.381(2) . ?
C24 C29 1.382(2) . ?
C25 C26 1.387(2) . ?
C26 C27 1.396(2) . ?
C27 C28 1.397(2) . ?
C27 C38 1.531(2) . ?
C28 C29 1.380(2) . ?
C30 C31 1.531(3) . ?
C30 C32 1.534(3) . ?
C30 C33 1.532(3) . ?
C34 C35 1.536(3) . ?
C34 C36 1.526(3) . ?
C34 C37 1.537(2) . ?
C38 C39 1.517(3) . ?
C38 C40 1.520(3) . ?
C38 C41 1.528(2) . ?
B1 N1 1.596(11) . ?
B1 C1 1.626(15) . ?
B1 N1A 1.57(2) . ?
B1 C1A 1.72(2) . ?
N1 C7 1.350(10) . ?
N1 C11 1.330(10) . ?
C1 C2 1.411(14) . ?
C1 C6 1.408(13) . ?
C2 C3 1.390(7) . ?
C3 C4 1.389(6) . ?
C4 C5 1.389(6) . ?
C5 C6 1.386(10) . ?
C6 C7 1.466(6) . ?
C7 C8 1.400(9) . ?
C8 C9 1.385(7) . ?
C9 C10 1.376(6) . ?
C10 C11 1.387(6) . ?
Cl1 C42 1.730(8) . ?
N1A C7A 1.36(2) . ?
N1A C11A 1.33(2) . ?
C1A C2A 1.42(2) . ?
C1A C6A 1.40(2) . ?
C2A C3A 1.393(10) . ?
C3A C4A 1.382(10) . ?
C4A C5A 1.385(11) . ?
C5A C6A 1.391(16) . ?
C6A C7A 1.460(11) . ?
C7A C8A 1.411(17) . ?
C8A C9A 1.375(10) . ?
C9A C10A 1.373(9) . ?
C10A C11A 1.375(12) . ?
Cl2 C42 1.773(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N2 C24 117.28(12) . . ?
C19 N2 C13 122.19(12) . . ?
C19 N2 C24 118.17(12) . . ?
C13 C12 B1 120.03(13) . . ?
C17 C12 C13 117.59(13) . . ?
C17 C12 B1 122.37(13) . . ?
C12 C13 N2 120.64(13) . . ?
C14 C13 N2 119.89(13) . . ?
C14 C13 C12 119.46(13) . . ?
C15 C14 C13 120.55(14) . . ?
C14 C15 C16 121.99(14) . . ?
C15 C16 C17 116.09(14) . . ?
C15 C16 C30 122.92(14) . . ?
C17 C16 C30 120.91(14) . . ?
C16 C17 C12 124.32(14) . . ?
C19 C18 B1 119.57(13) . . ?
C23 C18 C19 117.80(13) . . ?
C23 C18 B1 122.49(13) . . ?
C18 C19 N2 120.83(13) . . ?
C20 C19 N2 119.99(14) . . ?
C20 C19 C18 119.17(14) . . ?
C21 C20 C19 120.44(15) . . ?
C20 C21 C22 122.46(15) . . ?
C21 C22 C23 115.78(14) . . ?
C21 C22 C34 120.10(14) . . ?
C23 C22 C34 124.09(15) . . ?
C22 C23 C18 124.08(14) . . ?
C25 C24 N2 120.02(14) . . ?
C25 C24 C29 119.04(14) . . ?
C29 C24 N2 120.93(13) . . ?
C24 C25 C26 120.35(15) . . ?
C25 C26 C27 121.57(14) . . ?
C26 C27 C28 116.81(14) . . ?
C26 C27 C38 122.11(13) . . ?
C28 C27 C38 121.04(14) . . ?
C29 C28 C27 121.69(15) . . ?
C28 C29 C24 120.48(14) . . ?
C16 C30 C31 110.83(14) . . ?
C16 C30 C32 108.00(15) . . ?
C16 C30 C33 111.70(15) . . ?
C31 C30 C32 109.03(16) . . ?
C31 C30 C33 107.68(17) . . ?
C33 C30 C32 109.56(18) . . ?
C22 C34 C37 110.13(14) . . ?
C35 C34 C22 109.15(14) . . ?
C35 C34 C37 108.90(15) . . ?
C36 C34 C22 112.28(14) . . ?
C36 C34 C35 108.81(15) . . ?
C36 C34 C37 107.50(15) . . ?
C39 C38 C27 107.87(14) . . ?
C39 C38 C40 109.75(19) . . ?
C39 C38 C41 110.16(19) . . ?
C40 C38 C27 111.54(14) . . ?
C40 C38 C41 106.48(16) . . ?
C41 C38 C27 111.05(14) . . ?
C12 B1 C18 109.94(13) . . ?
C12 B1 C1 115.1(7) . . ?
C12 B1 C1A 111.4(14) . . ?
C18 B1 C1 115.5(8) . . ?
C18 B1 C1A 110.5(14) . . ?
N1 B1 C12 108.6(7) . . ?
N1 B1 C18 109.5(7) . . ?
N1 B1 C1 97.2(4) . . ?
N1A B1 C12 111.0(12) . . ?
N1A B1 C18 119.0(12) . . ?
N1A B1 C1A 94.1(8) . . ?
C7 N1 B1 113.7(7) . . ?
C11 N1 B1 126.4(7) . . ?
C11 N1 C7 119.9(8) . . ?
C2 C1 B1 132.2(10) . . ?
C6 C1 B1 108.6(9) . . ?
C6 C1 C2 118.4(11) . . ?
C3 C2 C1 120.0(9) . . ?
C4 C3 C2 120.2(6) . . ?
C5 C4 C3 120.7(6) . . ?
C6 C5 C4 119.4(7) . . ?
C1 C6 C7 111.3(10) . . ?
C5 C6 C1 121.1(9) . . ?
C5 C6 C7 127.5(8) . . ?
N1 C7 C6 108.9(9) . . ?
N1 C7 C8 121.7(7) . . ?
C8 C7 C6 129.2(8) . . ?
C9 C8 C7 117.8(6) . . ?
C10 C9 C8 119.6(5) . . ?
C9 C10 C11 119.8(5) . . ?
N1 C11 C10 121.1(7) . . ?
C7A N1A B1 117.4(16) . . ?
C11A N1A B1 124.7(16) . . ?
C11A N1A C7A 117.7(18) . . ?
C2A C1A B1 130.8(15) . . ?
C6A C1A B1 108.1(15) . . ?
C6A C1A C2A 121.0(18) . . ?
C3A C2A C1A 118.8(13) . . ?
C4A C3A C2A 119.8(10) . . ?
C3A C4A C5A 121.1(10) . . ?
C4A C5A C6A 120.7(11) . . ?
C1A C6A C7A 112.4(17) . . ?
C5A C6A C1A 118.4(14) . . ?
C5A C6A C7A 128.8(15) . . ?
N1A C7A C6A 107.9(17) . . ?
N1A C7A C8A 123.2(15) . . ?
C8A C7A C6A 128.8(16) . . ?
C9A C8A C7A 115.9(12) . . ?
C10A C9A C8A 121.3(11) . . ?
C9A C10A C11A 119.1(12) . . ?
N1A C11A C10A 122.5(17) . . ?
Cl1 C42 Cl2 111.6(3) . . ?

_olex2_exptl_crystal_mounting_method 
'Mounted on MiTeGen Dual-Thickness MicroMounts in paraffin oil.'
_olex2_submission_special_instructions 'No special instructions were received'
