# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_JF024
_database_code_depnum_ccdc_archive 'CCDC 1035566'
_audit_update_record             
;
2014-11-23 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;
_audit_creation_date             2014-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_formula_moiety         'C23 H21 B F10 N2'
_chemical_formula_sum            'C23 H21 B F10 N2'
_chemical_formula_weight         526.24
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   19.6299(9)
_cell_length_b                   19.4566(9)
_cell_length_c                   12.2650(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.938(2)
_cell_angle_gamma                90
_cell_volume                     4583.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9958
_cell_measurement_theta_max      27.291
_cell_measurement_theta_min      2.418
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0669 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.8873.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5252
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             2145.8804
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            77613
_diffrn_reflns_theta_full        27.5805
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         1.49
_diffrn_ambient_temperature      150.02
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              25
_reflns_limit_h_min              -25
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                7086
_reflns_number_total             10567
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.4438
_refine_diff_density_min         -0.4090
_refine_diff_density_rms         0.1035
_refine_ls_d_res_high            0.7675
_refine_ls_d_res_low             13.6682
_refine_ls_goodness_of_fit_ref   1.0948
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     660
_refine_ls_number_reflns         10567
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.0948
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+6.2019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1391
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H14(0.06) H15(0.06) H17a(0.06) H17b(0.06) H17c(0.06) H18a(0.06)
 H18b(0.06) H18c(0.06) H19a(0.06) H19b(0.06) H19c(0.06) H21a(0.06) H21b(0.06)
 H21c(0.06) H22a(0.06) H22b(0.06) H22c(0.06) H23a(0.06) H23b(0.06) H23c(0.06)
 H1(0.06) H37(0.06) H38(0.06) H40a(0.06) H40b(0.06) H40c(0.06) H41a(0.06)
 H41b(0.06) H41c(0.06) H42a(0.06) H42b(0.06) H42c(0.06) H44a(0.06) H44b(0.06)
 H44c(0.06) H45a(0.06) H45b(0.06) H45c(0.06) H46a(0.06) H46b(0.06) H46c(0.06)
 H2(0.06)
2.a Ternary CH refined with riding coordinates:
 B1(H1), B2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C37(H37), C38(H38)
2.c Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C19(H19a,H19b,H19c), C21(H21a,H21b,
 H21c), C22(H22a,H22b,H22c), C23(H23a,H23b,H23c), C40(H40a,H40b,H40c), C41(H41a,
 H41b,H41c), C42(H42a,H42b,H42c), C44(H44a,H44b,H44c), C45(H45a,H45b,H45c),
 C46(H46a,H46b,H46c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
F1 F 0.11382(9) 0.37622(8) 0.93506(13) 0.0365(4) Uani 1.000000 .
F2 F 0.20464(10) 0.45258(10) 1.07352(14) 0.0493(5) Uani 1.000000 .
F3 F 0.22905(9) 0.58514(10) 1.02263(15) 0.0460(5) Uani 1.000000 .
F4 F 0.15643(8) 0.64124(8) 0.82953(15) 0.0386(4) Uani 1.000000 .
F5 F 0.06343(8) 0.56608(7) 0.68986(12) 0.0279(3) Uani 1.000000 .
F6 F -0.04881(8) 0.54365(8) 0.78786(13) 0.0303(4) Uani 1.000000 .
F7 F -0.17162(8) 0.58802(8) 0.68082(15) 0.0388(4) Uani 1.000000 .
F8 F -0.24041(8) 0.52443(10) 0.49164(15) 0.0444(5) Uani 1.000000 .
F9 F -0.18087(8) 0.41458(10) 0.41059(14) 0.0407(4) Uani 1.000000 .
F10 F -0.05481(8) 0.37041(8) 0.51461(13) 0.0305(4) Uani 1.000000 .
N1 N 0.07306(10) 0.29203(10) 0.69985(16) 0.0205(4) Uani 1.000000 .
N2 N -0.01607(10) 0.30337(11) 0.77853(17) 0.0222(5) Uani 1.000000 .
C1 C 0.08248(12) 0.46760(13) 0.8053(2) 0.0210(5) Uani 1.000000 .
C2 C 0.12085(13) 0.44277(14) 0.9044(2) 0.0259(6) Uani 1.000000 .
C3 C 0.16975(14) 0.48064(16) 0.9780(2) 0.0322(7) Uani 1.000000 .
C4 C 0.18208(14) 0.54729(15) 0.9524(2) 0.0317(6) Uani 1.000000 .
C5 C 0.14536(13) 0.57554(14) 0.8547(2) 0.0269(6) Uani 1.000000 .
C6 C 0.09720(13) 0.53570(13) 0.7849(2) 0.0231(5) Uani 1.000000 .
C7 C -0.04438(12) 0.45458(12) 0.6556(2) 0.0194(5) Uani 1.000000 .
C8 C -0.07792(13) 0.50985(13) 0.6929(2) 0.0230(5) Uani 1.000000 .
C9 C -0.14278(13) 0.53390(13) 0.6393(2) 0.0270(6) Uani 1.000000 .
C10 C -0.17727(13) 0.50218(15) 0.5438(2) 0.0281(6) Uani 1.000000 .
C11 C -0.14665(13) 0.44723(14) 0.5029(2) 0.0267(6) Uani 1.000000 .
C12 C -0.08174(13) 0.42566(13) 0.5577(2) 0.0220(5) Uani 1.000000 .
C13 C 0.03071(12) 0.33996(13) 0.7333(2) 0.0196(5) Uani 1.000000 .
C14 C 0.04997(14) 0.22698(13) 0.7194(2) 0.0276(6) Uani 1.000000 .
H14 H 0.06960(14) 0.18478(13) 0.7020(2) 0.060000 Uiso 1.000000 R
C15 C -0.00479(14) 0.23405(14) 0.7672(2) 0.0286(6) Uani 1.000000 .
H15 H -0.03132(14) 0.19777(14) 0.7894(2) 0.060000 Uiso 1.000000 R
C16 C -0.07180(14) 0.32796(15) 0.8390(2) 0.0299(6) Uani 1.000000 .
C17 C -0.08296(16) 0.27172(17) 0.9221(3) 0.0417(8) Uani 1.000000 .
H17a H -0.0380(2) 0.2589(8) 0.9689(12) 0.060000 Uiso 1.000000 GR
H17b H -0.1138(9) 0.2892(4) 0.9693(12) 0.060000 Uiso 1.000000 GR
H17c H -0.1042(10) 0.2313(4) 0.8810(3) 0.060000 Uiso 1.000000 GR
C18 C -0.04766(16) 0.39161(16) 0.9070(2) 0.0367(7) Uani 1.000000 .
H18a H -0.0088(7) 0.3797(3) 0.9681(11) 0.060000 Uiso 1.000000 GR
H18b H -0.0324(10) 0.4263(4) 0.8592(5) 0.060000 Uiso 1.000000 GR
H18c H -0.0862(4) 0.4101(6) 0.9376(15) 0.060000 Uiso 1.000000 GR
C19 C -0.14043(14) 0.33796(17) 0.7559(3) 0.0404(8) Uani 1.000000 .
H19a H -0.1780(2) 0.3452(11) 0.7964(3) 0.060000 Uiso 1.000000 GR
H19b H -0.1369(4) 0.3781(7) 0.7091(12) 0.060000 Uiso 1.000000 GR
H19c H -0.1506(6) 0.2970(5) 0.7089(12) 0.060000 Uiso 1.000000 GR
C20 C 0.13668(13) 0.30162(14) 0.6482(2) 0.0249(6) Uani 1.000000 .
C21 C 0.18389(13) 0.35834(15) 0.7074(2) 0.0309(6) Uani 1.000000 .
H21a H 0.1600(4) 0.4027(2) 0.6936(15) 0.060000 Uiso 1.000000 GR
H21b H 0.1950(9) 0.3492(6) 0.7877(3) 0.060000 Uiso 1.000000 GR
H21c H 0.2270(5) 0.3596(7) 0.6790(13) 0.060000 Uiso 1.000000 GR
C22 C 0.11242(15) 0.31510(16) 0.5236(2) 0.0332(7) Uani 1.000000 .
H22a H 0.0838(9) 0.3568(6) 0.5125(2) 0.060000 Uiso 1.000000 GR
H22b H 0.15303(15) 0.3212(11) 0.4897(4) 0.060000 Uiso 1.000000 GR
H22c H 0.0848(9) 0.2760(5) 0.4888(4) 0.060000 Uiso 1.000000 GR
C23 C 0.17928(15) 0.23465(15) 0.6643(3) 0.0368(7) Uani 1.000000 .
H23a H 0.2226(5) 0.2412(4) 0.6376(16) 0.060000 Uiso 1.000000 GR
H23b H 0.1903(9) 0.2225(6) 0.7435(3) 0.060000 Uiso 1.000000 GR
H23c H 0.1521(5) 0.1976(3) 0.6218(14) 0.060000 Uiso 1.000000 GR
B1 B 0.03330(14) 0.42289(14) 0.7069(2) 0.0193(6) Uani 1.000000 .
H1 H 0.05792(14) 0.42549(14) 0.6433(2) 0.060000 Uiso 1.000000 R
F11 F 0.45365(7) 0.30535(7) 0.79721(12) 0.0268(3) Uani 1.000000 .
F12 F 0.35470(8) 0.37880(8) 0.66437(14) 0.0341(4) Uani 1.000000 .
F13 F 0.28816(8) 0.32767(9) 0.46357(14) 0.0381(4) Uani 1.000000 .
F14 F 0.32599(8) 0.20261(9) 0.39567(13) 0.0376(4) Uani 1.000000 .
F15 F 0.42272(8) 0.12822(8) 0.52645(13) 0.0319(4) Uani 1.000000 .
F16 F 0.57612(8) 0.10985(8) 0.96072(13) 0.0342(4) Uani 1.000000 .
F17 F 0.70126(8) 0.15160(9) 1.07176(13) 0.0396(4) Uani 1.000000 .
F18 F 0.76376(8) 0.26196(9) 1.00022(14) 0.0404(4) Uani 1.000000 .
F19 F 0.69805(8) 0.33052(8) 0.81363(14) 0.0352(4) Uani 1.000000 .
F20 F 0.57508(7) 0.29002(7) 0.70025(12) 0.0264(3) Uani 1.000000 .
N3 N 0.45486(10) 0.03518(10) 0.76364(17) 0.0205(4) Uani 1.000000 .
N4 N 0.54591(10) 0.04903(10) 0.69008(17) 0.0205(4) Uani 1.000000 .
C24 C 0.44465(12) 0.21329(12) 0.6682(2) 0.0198(5) Uani 1.000000 .
C25 C 0.42421(12) 0.27813(13) 0.6969(2) 0.0209(5) Uani 1.000000 .
C26 C 0.37302(13) 0.31707(13) 0.6304(2) 0.0244(6) Uani 1.000000 .
C27 C 0.33947(13) 0.29160(14) 0.5285(2) 0.0257(6) Uani 1.000000 .
C28 C 0.35865(13) 0.22852(14) 0.4944(2) 0.0260(6) Uani 1.000000 .
C29 C 0.40987(13) 0.19154(13) 0.5645(2) 0.0224(5) Uani 1.000000 .
C30 C 0.56903(12) 0.19695(12) 0.8246(2) 0.0186(5) Uani 1.000000 .
C31 C 0.60442(13) 0.16574(13) 0.9212(2) 0.0225(5) Uani 1.000000 .
C32 C 0.66909(13) 0.18592(14) 0.9812(2) 0.0247(6) Uani 1.000000 .
C33 C 0.70116(13) 0.24132(14) 0.9443(2) 0.0243(6) Uani 1.000000 .
C34 C 0.66794(13) 0.27579(13) 0.8497(2) 0.0222(5) Uani 1.000000 .
C35 C 0.60346(12) 0.25327(12) 0.7927(2) 0.0192(5) Uani 1.000000 .
C36 C 0.49722(12) 0.08428(12) 0.73367(19) 0.0184(5) Uani 1.000000 .
C37 C 0.47961(14) -0.02933(13) 0.7436(2) 0.0279(6) Uani 1.000000 .
H37 H 0.46037(14) -0.07213(13) 0.7592(2) 0.060000 Uiso 1.000000 R
C38 C 0.53525(14) -0.02056(13) 0.6987(2) 0.0274(6) Uani 1.000000 .
H38 H 0.56271(14) -0.05604(13) 0.6764(2) 0.060000 Uiso 1.000000 R
C39 C 0.38961(13) 0.04312(13) 0.8115(2) 0.0236(5) Uani 1.000000 .
C40 C 0.34803(15) -0.02409(14) 0.7914(2) 0.0335(7) Uani 1.000000 .
H40a H 0.3385(9) -0.0352(6) 0.7117(3) 0.060000 Uiso 1.000000 GR
H40b H 0.3751(5) -0.0613(3) 0.8335(14) 0.060000 Uiso 1.000000 GR
H40c H 0.3039(5) -0.0187(4) 0.8161(16) 0.060000 Uiso 1.000000 GR
C41 C 0.41085(14) 0.05534(14) 0.9367(2) 0.0271(6) Uani 1.000000 .
H41a H 0.4413(9) 0.0179(6) 0.9711(3) 0.060000 Uiso 1.000000 GR
H41b H 0.4358(10) 0.0991(5) 0.9505(2) 0.060000 Uiso 1.000000 GR
H41c H 0.36916(16) 0.0568(11) 0.9689(4) 0.060000 Uiso 1.000000 GR
C42 C 0.34268(13) 0.09947(14) 0.7511(2) 0.0282(6) Uani 1.000000 .
H42a H 0.3647(5) 0.14431(16) 0.7698(14) 0.060000 Uiso 1.000000 GR
H42b H 0.3354(9) 0.0921(6) 0.6704(2) 0.060000 Uiso 1.000000 GR
H42c H 0.2977(4) 0.0983(7) 0.7740(13) 0.060000 Uiso 1.000000 GR
C43 C 0.60447(13) 0.07449(14) 0.6361(2) 0.0258(6) Uani 1.000000 .
C44 C 0.67087(14) 0.08314(17) 0.7264(3) 0.0364(7) Uani 1.000000 .
H44a H 0.7107(2) 0.0906(11) 0.6911(3) 0.060000 Uiso 1.000000 GR
H44b H 0.6656(5) 0.1227(7) 0.7733(11) 0.060000 Uiso 1.000000 GR
H44c H 0.6787(6) 0.0416(5) 0.7724(11) 0.060000 Uiso 1.000000 GR
C45 C 0.58345(15) 0.13974(15) 0.5707(2) 0.0313(6) Uani 1.000000 .
H45a H 0.5446(7) 0.1300(3) 0.5084(11) 0.060000 Uiso 1.000000 GR
H45b H 0.5691(11) 0.1743(4) 0.6195(5) 0.060000 Uiso 1.000000 GR
H45c H 0.6231(4) 0.1572(6) 0.5417(15) 0.060000 Uiso 1.000000 GR
C46 C 0.61825(15) 0.02003(16) 0.5534(2) 0.0354(7) Uani 1.000000 .
H46a H 0.57408(19) 0.0063(8) 0.5052(12) 0.060000 Uiso 1.000000 GR
H46b H 0.6491(9) 0.0391(4) 0.5076(12) 0.060000 Uiso 1.000000 GR
H46c H 0.6404(10) -0.0201(5) 0.5943(3) 0.060000 Uiso 1.000000 GR
B2 B 0.49276(14) 0.16595(14) 0.7649(2) 0.0182(6) Uani 1.000000 .
H2 H 0.46624(14) 0.16583(14) 0.8263(2) 0.060000 Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.363(3) . ?
F2 C3 1.344(3) . ?
F3 C4 1.344(3) . ?
F4 C5 1.343(3) . ?
F5 C6 1.352(3) . ?
F6 C8 1.356(3) . ?
F7 C9 1.345(3) . ?
F8 C10 1.343(3) . ?
F9 C11 1.350(3) . ?
F10 C12 1.353(3) . ?
N1 C13 1.367(3) . ?
N1 C14 1.382(3) . ?
N1 C20 1.524(3) . ?
N2 C13 1.367(3) . ?
N2 C15 1.379(3) . ?
N2 C16 1.521(3) . ?
C1 C2 1.378(3) . ?
C1 C6 1.390(4) . ?
C1 B1 1.632(4) . ?
C2 C3 1.386(4) . ?
C3 C4 1.368(4) . ?
C4 C5 1.378(4) . ?
C5 C6 1.376(4) . ?
C7 C8 1.387(3) . ?
C7 C12 1.390(3) . ?
C7 B1 1.645(3) . ?
C8 C9 1.388(4) . ?
C9 C10 1.372(4) . ?
C10 C11 1.371(4) . ?
C11 C12 1.377(3) . ?
C13 B1 1.649(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.334(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.542(4) . ?
C16 C18 1.513(4) . ?
C16 C19 1.524(4) . ?
C17 H17a 0.9800 . ?
C17 H17b 0.9800 . ?
C17 H17c 0.9800 . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
C19 H19a 0.9800 . ?
C19 H19b 0.9800 . ?
C19 H19c 0.9800 . ?
C20 C21 1.525(4) . ?
C20 C22 1.526(4) . ?
C20 C23 1.539(4) . ?
C21 H21a 0.9800 . ?
C21 H21b 0.9800 . ?
C21 H21c 0.9800 . ?
C22 H22a 0.9800 . ?
C22 H22b 0.9800 . ?
C22 H22c 0.9800 . ?
C23 H23a 0.9800 . ?
C23 H23b 0.9800 . ?
C23 H23c 0.9800 . ?
B1 H1 1.0000 . ?
F11 C25 1.354(3) . ?
F12 C26 1.344(3) . ?
F13 C27 1.345(3) . ?
F14 C28 1.345(3) . ?
F15 C29 1.360(3) . ?
F16 C31 1.356(3) . ?
F17 C32 1.337(3) . ?
F18 C33 1.339(3) . ?
F19 C34 1.337(3) . ?
F20 C35 1.359(3) . ?
N3 C36 1.366(3) . ?
N3 C37 1.386(3) . ?
N3 C39 1.523(3) . ?
N4 C36 1.371(3) . ?
N4 C38 1.377(3) . ?
N4 C43 1.523(3) . ?
C24 C25 1.391(3) . ?
C24 C29 1.379(3) . ?
C24 B2 1.639(4) . ?
C25 C26 1.382(3) . ?
C26 C27 1.379(4) . ?
C27 C28 1.374(4) . ?
C28 C29 1.382(4) . ?
C30 C31 1.384(3) . ?
C30 C35 1.385(3) . ?
C30 B2 1.639(3) . ?
C31 C32 1.386(3) . ?
C32 C33 1.372(4) . ?
C33 C34 1.381(4) . ?
C34 C35 1.384(3) . ?
C36 B2 1.641(4) . ?
C37 H37 0.9500 . ?
C37 C38 1.332(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.534(3) . ?
C39 C41 1.523(4) . ?
C39 C42 1.523(4) . ?
C40 H40a 0.9800 . ?
C40 H40b 0.9800 . ?
C40 H40c 0.9800 . ?
C41 H41a 0.9800 . ?
C41 H41b 0.9800 . ?
C41 H41c 0.9800 . ?
C42 H42a 0.9800 . ?
C42 H42b 0.9800 . ?
C42 H42c 0.9800 . ?
C43 C44 1.535(4) . ?
C43 C45 1.513(4) . ?
C43 C46 1.529(4) . ?
C44 H44a 0.9800 . ?
C44 H44b 0.9800 . ?
C44 H44c 0.9800 . ?
C45 H45a 0.9800 . ?
C45 H45b 0.9800 . ?
C45 H45c 0.9800 . ?
C46 H46a 0.9800 . ?
C46 H46b 0.9800 . ?
C46 H46c 0.9800 . ?
B2 H2 1.0000 . ?

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
C14 N1 C13 109.3(2) . . ?
C20 N1 C13 130.0(2) . . ?
C20 N1 C14 120.7(2) . . ?
C15 N2 C13 109.5(2) . . ?
C16 N2 C13 130.2(2) . . ?
C16 N2 C15 120.3(2) . . ?
C6 C1 C2 113.4(2) . . ?
B1 C1 C2 126.7(2) . . ?
B1 C1 C6 119.2(2) . . ?
C1 C2 F1 120.6(2) . . ?
C3 C2 F1 114.9(2) . . ?
C3 C2 C1 124.5(3) . . ?
C2 C3 F2 120.7(3) . . ?
C4 C3 F2 120.2(3) . . ?
C4 C3 C2 119.1(2) . . ?
C3 C4 F3 120.2(3) . . ?
C5 C4 F3 120.3(3) . . ?
C5 C4 C3 119.5(2) . . ?
C4 C5 F4 119.9(2) . . ?
C6 C5 F4 121.1(2) . . ?
C6 C5 C4 119.0(3) . . ?
C1 C6 F5 119.3(2) . . ?
C5 C6 F5 116.2(2) . . ?
C5 C6 C1 124.5(2) . . ?
C12 C7 C8 113.4(2) . . ?
B1 C7 C8 129.1(2) . . ?
B1 C7 C12 117.4(2) . . ?
C7 C8 F6 121.0(2) . . ?
C9 C8 F6 115.2(2) . . ?
C9 C8 C7 123.8(2) . . ?
C8 C9 F7 120.1(2) . . ?
C10 C9 F7 120.2(2) . . ?
C10 C9 C8 119.7(2) . . ?
C9 C10 F8 120.3(2) . . ?
C11 C10 F8 120.6(2) . . ?
C11 C10 C9 119.1(2) . . ?
C10 C11 F9 119.6(2) . . ?
C12 C11 F9 121.0(2) . . ?
C12 C11 C10 119.4(2) . . ?
C7 C12 F10 118.7(2) . . ?
C11 C12 F10 116.7(2) . . ?
C11 C12 C7 124.6(2) . . ?
N2 C13 N1 105.5(2) . . ?
B1 C13 N1 124.3(2) . . ?
B1 C13 N2 129.8(2) . . ?
H14 C14 N1 126.12(15) . . ?
C15 C14 N1 107.8(2) . . ?
C15 C14 H14 126.12(16) . . ?
C14 C15 N2 107.8(2) . . ?
H15 C15 N2 126.09(15) . . ?
H15 C15 C14 126.09(16) . . ?
C17 C16 N2 108.3(2) . . ?
C18 C16 N2 110.6(2) . . ?
C18 C16 C17 106.7(2) . . ?
C19 C16 N2 109.9(2) . . ?
C19 C16 C17 107.8(2) . . ?
C19 C16 C18 113.4(2) . . ?
H17a C17 C16 109.5 . . ?
H17b C17 C16 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 C16 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
H18a C18 C16 109.5 . . ?
H18b C18 C16 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C16 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
H19a C19 C16 109.5 . . ?
H19b C19 C16 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 C16 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
C21 C20 N1 111.1(2) . . ?
C22 C20 N1 108.9(2) . . ?
C22 C20 C21 112.7(2) . . ?
C23 C20 N1 108.3(2) . . ?
C23 C20 C21 106.9(2) . . ?
C23 C20 C22 108.8(2) . . ?
H21a C21 C20 109.5 . . ?
H21b C21 C20 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 C20 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?
H22a C22 C20 109.5 . . ?
H22b C22 C20 109.5 . . ?
H22b C22 H22a 109.5 . . ?
H22c C22 C20 109.5 . . ?
H22c C22 H22a 109.5 . . ?
H22c C22 H22b 109.5 . . ?
H23a C23 C20 109.5 . . ?
H23b C23 C20 109.5 . . ?
H23b C23 H23a 109.5 . . ?
H23c C23 C20 109.5 . . ?
H23c C23 H23a 109.5 . . ?
H23c C23 H23b 109.5 . . ?
C7 B1 C1 116.3(2) . . ?
C13 B1 C1 114.5(2) . . ?
C13 B1 C7 112.2(2) . . ?
H1 B1 C1 104.02(13) . . ?
H1 B1 C7 104.02(13) . . ?
H1 B1 C13 104.02(13) . . ?
C37 N3 C36 109.3(2) . . ?
C39 N3 C36 129.8(2) . . ?
C39 N3 C37 120.9(2) . . ?
C38 N4 C36 109.4(2) . . ?
C43 N4 C36 131.0(2) . . ?
C43 N4 C38 119.5(2) . . ?
C29 C24 C25 113.5(2) . . ?
B2 C24 C25 118.7(2) . . ?
B2 C24 C29 126.6(2) . . ?
C24 C25 F11 119.6(2) . . ?
C26 C25 F11 116.3(2) . . ?
C26 C25 C24 124.1(2) . . ?
C25 C26 F12 121.0(2) . . ?
C27 C26 F12 119.6(2) . . ?
C27 C26 C25 119.4(2) . . ?
C26 C27 F13 120.5(2) . . ?
C28 C27 F13 120.3(2) . . ?
C28 C27 C26 119.2(2) . . ?
C27 C28 F14 119.9(2) . . ?
C29 C28 F14 121.0(2) . . ?
C29 C28 C27 119.0(2) . . ?
C24 C29 F15 120.2(2) . . ?
C28 C29 F15 114.9(2) . . ?
C28 C29 C24 124.9(2) . . ?
C35 C30 C31 113.6(2) . . ?
B2 C30 C31 118.1(2) . . ?
B2 C30 C35 128.2(2) . . ?
C30 C31 F16 119.2(2) . . ?
C32 C31 F16 115.8(2) . . ?
C32 C31 C30 124.9(2) . . ?
C31 C32 F17 121.5(2) . . ?
C33 C32 F17 119.8(2) . . ?
C33 C32 C31 118.7(2) . . ?
C32 C33 F18 120.1(2) . . ?
C34 C33 F18 120.6(2) . . ?
C34 C33 C32 119.3(2) . . ?
C33 C34 F19 120.0(2) . . ?
C35 C34 F19 120.4(2) . . ?
C35 C34 C33 119.6(2) . . ?
C30 C35 F20 120.8(2) . . ?
C34 C35 F20 115.4(2) . . ?
C34 C35 C30 123.8(2) . . ?
N4 C36 N3 105.5(2) . . ?
B2 C36 N3 123.3(2) . . ?
B2 C36 N4 130.6(2) . . ?
H37 C37 N3 126.13(14) . . ?
C38 C37 N3 107.7(2) . . ?
C38 C37 H37 126.13(16) . . ?
C37 C38 N4 107.9(2) . . ?
H38 C38 N4 126.03(15) . . ?
H38 C38 C37 126.03(16) . . ?
C40 C39 N3 108.3(2) . . ?
C41 C39 N3 109.1(2) . . ?
C41 C39 C40 108.7(2) . . ?
C42 C39 N3 110.9(2) . . ?
C42 C39 C40 106.7(2) . . ?
C42 C39 C41 113.0(2) . . ?
H40a C40 C39 109.5 . . ?
H40b C40 C39 109.5 . . ?
H40b C40 H40a 109.5 . . ?
H40c C40 C39 109.5 . . ?
H40c C40 H40a 109.5 . . ?
H40c C40 H40b 109.5 . . ?
H41a C41 C39 109.5 . . ?
H41b C41 C39 109.5 . . ?
H41b C41 H41a 109.5 . . ?
H41c C41 C39 109.5 . . ?
H41c C41 H41a 109.5 . . ?
H41c C41 H41b 109.5 . . ?
H42a C42 C39 109.5 . . ?
H42b C42 C39 109.5 . . ?
H42b C42 H42a 109.5 . . ?
H42c C42 C39 109.5 . . ?
H42c C42 H42a 109.5 . . ?
H42c C42 H42b 109.5 . . ?
C44 C43 N4 109.1(2) . . ?
C45 C43 N4 110.8(2) . . ?
C45 C43 C44 112.9(2) . . ?
C46 C43 N4 108.4(2) . . ?
C46 C43 C44 108.3(2) . . ?
C46 C43 C45 107.2(2) . . ?
H44a C44 C43 109.5 . . ?
H44b C44 C43 109.5 . . ?
H44b C44 H44a 109.5 . . ?
H44c C44 C43 109.5 . . ?
H44c C44 H44a 109.5 . . ?
H44c C44 H44b 109.5 . . ?
H45a C45 C43 109.5 . . ?
H45b C45 C43 109.5 . . ?
H45b C45 H45a 109.5 . . ?
H45c C45 C43 109.5 . . ?
H45c C45 H45a 109.5 . . ?
H45c C45 H45b 109.5 . . ?
H46a C46 C43 109.5 . . ?
H46b C46 C43 109.5 . . ?
H46b C46 H46a 109.5 . . ?
H46c C46 C43 109.5 . . ?
H46c C46 H46a 109.5 . . ?
H46c C46 H46b 109.5 . . ?
C30 B2 C24 116.9(2) . . ?
C36 B2 C24 115.20(19) . . ?
C36 B2 C30 111.9(2) . . ?
H2 B2 C24 103.58(13) . . ?
H2 B2 C30 103.58(13) . . ?
H2 B2 C36 103.58(13) . . ?

_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_jf034_0m
_database_code_depnum_ccdc_archive 'CCDC 1035567'
_audit_update_record             
;
2014-11-23 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;
_audit_creation_date             2014-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_formula_moiety         'C23 H18.71 B F10 N2'
_chemical_formula_sum            'C23 H18.711 B F10 N2'
_chemical_formula_weight         523.94
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.5423(18)
_cell_length_b                   12.863(2)
_cell_length_c                   15.801(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.409(6)
_cell_angle_gamma                90
_cell_volume                     2341.7(6)
_cell_measurement_temperature    150(2)
_cell_formula_units_Z            4
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0581 before and 0.0504 after correction.
The Ratio of minimum to maximum transmission is 0.9225.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.4860
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1063.7835
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19692
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         2.04
_diffrn_ambient_temperature      149.7
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9783
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -14
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -11
_reflns_number_gt                3100
_reflns_number_total             5311
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.2215
_refine_diff_density_min         -1.1698
_refine_diff_density_rms         0.1128
_refine_ls_d_res_high            0.7673
_refine_ls_d_res_low             9.9683
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0563
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    11
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0754
_refine_ls_restrained_S_all      1.0563
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+4.9380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1836
_olex2_refinement_description    
;
1. Others
 Sof(C7A)=Sof(H7Aa)=Sof(H7Ab)=Sof(H7Ac)=Sof(C11)=Sof(H11a)=Sof(H11b)=Sof(H11c)=
 Sof(B2)=1-FVAR(1)
 Sof(C7)=Sof(H7a)=Sof(H7b)=Sof(C11A)=Sof(H11d)=Sof(H11e)=Sof(B1)=FVAR(1)
 Fixed Uiso: H1(0.06) H2(0.06) H5a(0.06) H5b(0.06) H5c(0.06) H6a(0.06)
 H6b(0.06) H6c(0.06) H7a(0.06) H7b(0.06) H7Aa(0.06) H7Ab(0.06) H7Ac(0.06)
 H9a(0.06) H9b(0.06) H9c(0.06) H10a(0.06) H10b(0.06) H10c(0.06) H11a(0.06)
 H11b(0.06) H11c(0.06) H11d(0.06) H11e(0.06)
2.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C11A(H11d,H11e)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
2.c Idealised Me refined as rotating group:
 C5(H5a,H5b,H5c), C6(H6a,H6b,H6c), C7A(H7Aa,H7Ab,H7Ac), C9(H9a,H9b,H9c),
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_disorder_group
F1 F 0.83200(18) 0.5317(2) 0.41391(12) 0.0550(7) Uani 1.000000 . .
F2 F 0.6224(2) 0.4718(2) 0.45442(14) 0.0572(7) Uani 1.000000 . .
F3 F 0.4287(2) 0.5371(3) 0.36215(17) 0.0788(9) Uani 1.000000 . .
F4 F 0.4517(2) 0.65979(19) 0.22311(16) 0.0620(7) Uani 1.000000 . .
F5 F 0.6599(2) 0.7205(3) 0.17940(17) 0.0889(11) Uani 1.000000 . .
F6 F 0.7740(2) 0.5527(3) 0.11800(17) 0.0968(12) Uani 1.000000 . .
F7 F 0.8321(3) 0.5692(2) -0.04137(16) 0.0768(9) Uani 1.000000 . .
F8 F 1.0073(3) 0.7006(3) -0.08363(15) 0.0924(11) Uani 1.000000 . .
F9 F 1.1234(2) 0.8125(2) 0.04063(15) 0.0647(7) Uani 1.000000 . .
F10 F 1.07064(19) 0.7946(2) 0.20127(13) 0.0648(8) Uani 1.000000 . .
N1 N 1.0118(2) 0.7391(2) 0.38920(17) 0.0333(7) Uani 1.000000 . .
N2 N 1.0729(2) 0.5876(2) 0.35315(16) 0.0308(6) Uani 1.000000 . .
C1 C 1.1077(3) 0.7163(3) 0.4425(2) 0.0427(9) Uani 1.000000 . .
H1 H 1.1404(3) 0.7588(3) 0.4869(2) 0.060000 Uiso 1.000000 R .
C2 C 1.1457(3) 0.6226(3) 0.4197(2) 0.0402(9) Uani 1.000000 . .
H2 H 1.2110(3) 0.5866(3) 0.4447(2) 0.060000 Uiso 1.000000 R .
C3 C 0.9901(3) 0.6601(3) 0.33457(19) 0.0298(7) Uani 1.000000 . .
C4 C 0.9360(3) 0.8337(3) 0.3896(2) 0.0347(8) Uani 1.000000 . .
C5 C 0.8644(4) 0.8280(3) 0.4678(3) 0.0553(11) Uani 1.000000 . .
H5a H 0.8161(16) 0.7654(11) 0.4648(8) 0.060000 Uiso 1.000000 GR .
H5b H 0.9167(4) 0.8255(19) 0.5190(3) 0.060000 Uiso 1.000000 GR .
H5c H 0.8147(16) 0.8896(10) 0.4698(9) 0.060000 Uiso 1.000000 GR .
C6 C 1.0137(4) 0.9298(3) 0.3916(3) 0.0503(10) Uani 1.000000 . .
H6a H 1.0638(15) 0.9298(10) 0.4438(8) 0.060000 Uiso 1.000000 GR .
H6b H 1.0618(15) 0.9289(10) 0.3425(9) 0.060000 Uiso 1.000000 GR .
H6c H 0.9654(4) 0.9925(3) 0.3896(16) 0.060000 Uiso 1.000000 GR .
C7 C 0.8598(8) 0.8226(9) 0.3050(7) 0.030(2) Uiso 0.645(10) . 1
H7a H 0.7775(8) 0.8378(9) 0.3145(7) 0.060000 Uiso 0.645(10) R 1
H7b H 0.8865(8) 0.8714(9) 0.2618(7) 0.060000 Uiso 0.645(10) R 1
C7A C 0.859(2) 0.8406(18) 0.3099(17) 0.079(9) Uani 0.355(10) . 2
H7Aa H 0.907(2) 0.841(6) 0.2607(17) 0.060000 Uiso 0.355(10) GR 2
H7Ab H 0.807(5) 0.781(4) 0.306(3) 0.060000 Uiso 0.355(10) GR 2
H7Ac H 0.813(5) 0.905(4) 0.311(3) 0.060000 Uiso 0.355(10) GR 2
C8 C 1.0860(3) 0.4872(3) 0.3057(2) 0.0359(8) Uani 1.000000 . .
C9 C 1.1741(4) 0.5051(5) 0.2379(3) 0.0836(18) Uani 1.000000 . .
H9a H 1.1407(9) 0.5525(15) 0.1944(9) 0.060000 Uiso 1.000000 GR .
H9b H 1.2451(9) 0.5357(19) 0.2644(4) 0.060000 Uiso 1.000000 GR .
H9c H 1.1926(16) 0.4386(5) 0.2117(11) 0.060000 Uiso 1.000000 GR .
C10 C 1.1286(5) 0.4054(4) 0.3677(3) 0.088(2) Uani 1.000000 . .
H10a H 1.2052(10) 0.4252(10) 0.3927(12) 0.060000 Uiso 1.000000 GR .
H10b H 1.0741(12) 0.3990(14) 0.4127(9) 0.060000 Uiso 1.000000 GR .
H10c H 1.134(2) 0.3387(6) 0.3384(4) 0.060000 Uiso 1.000000 GR .
C11 C 0.9639(19) 0.4471(15) 0.2725(14) 0.030(4) Uiso 0.355(10) . 1
H11a H 0.917(3) 0.431(6) 0.3207(14) 0.060000 Uiso 0.355(10) GR 1
H11b H 0.925(3) 0.501(3) 0.237(4) 0.060000 Uiso 0.355(10) GR 1
H11c H 0.9729(19) 0.384(4) 0.239(4) 0.060000 Uiso 0.355(10) GR 1
C11A C 0.9714(11) 0.4677(10) 0.2584(8) 0.053(3) Uani 0.645(10) . 2
H11d H 0.9817(11) 0.4416(10) 0.2004(8) 0.060000 Uiso 0.645(10) R 2
H11e H 0.9236(11) 0.4177(10) 0.2888(8) 0.060000 Uiso 0.645(10) R 2
C12 C 0.7585(3) 0.6265(4) 0.2916(2) 0.0589(13) Uani 1.000000 . .
C13 C 0.7407(3) 0.5634(3) 0.3620(2) 0.0392(9) Uani 1.000000 . .
C14 C 0.6329(3) 0.5325(3) 0.3856(2) 0.0348(8) Uani 1.000000 . .
C15 C 0.5356(3) 0.5650(3) 0.3389(2) 0.0414(9) Uani 1.000000 . .
C16 C 0.5472(3) 0.6272(3) 0.2690(2) 0.0403(9) Uani 1.000000 . .
C17 C 0.6560(4) 0.6557(4) 0.2477(2) 0.0539(12) Uani 1.000000 . .
C18 C 0.9152(4) 0.6771(4) 0.1688(2) 0.0679(16) Uani 1.000000 . .
C19 C 0.8615(4) 0.6205(4) 0.1025(3) 0.0617(14) Uani 1.000000 . .
C20 C 0.8903(4) 0.6262(3) 0.0193(2) 0.0508(10) Uani 1.000000 . .
C21 C 0.9782(4) 0.6922(3) -0.0026(2) 0.0500(11) Uani 1.000000 . .
C22 C 1.0363(3) 0.7484(3) 0.0604(2) 0.0430(9) Uani 1.000000 . .
C23 C 1.0058(3) 0.7385(3) 0.1428(2) 0.0461(10) Uani 1.000000 . .
B1 B 0.8748(5) 0.6975(4) 0.2723(3) 0.0269(16) Uani 0.645(10) . 1
B2 B 0.9080(9) 0.5975(8) 0.2567(6) 0.025(3) Uani 0.355(10) . 2


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.359(4) . ?
F2 C14 1.350(4) . ?
F3 C15 1.356(4) . ?
F4 C16 1.350(4) . ?
F5 C17 1.366(4) . ?
F6 C19 1.367(4) . ?
F7 C20 1.353(4) . ?
F8 C21 1.347(4) . ?
F9 C22 1.351(4) . ?
F10 C23 1.361(4) . ?
N1 C1 1.382(4) . ?
N1 C3 1.348(4) . ?
N1 C4 1.498(4) . ?
N2 C2 1.382(4) . ?
N2 C3 1.355(4) . ?
N2 C8 1.505(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.340(5) . ?
C2 H2 0.9500 . ?
C3 B1 1.678(6) . ?
C3 B2 1.710(10) . ?
C4 C5 1.528(5) . ?
C4 C6 1.527(5) . ?
C4 C7 1.562(12) . ?
C4 C7A 1.50(3) . ?
C5 H5a 0.9800 . ?
C5 H5b 0.9800 . ?
C5 H5c 0.9800 . ?
C6 H6a 0.9800 . ?
C6 H6b 0.9800 . ?
C6 H6c 0.9800 . ?
C7 H7a 0.9900 . ?
C7 H7b 0.9900 . ?
C7 B1 1.701(13) . ?
C7A H7Aa 0.9800 . ?
C7A H7Ab 0.9800 . ?
C7A H7Ac 0.9800 . ?
C8 C9 1.538(6) . ?
C8 C10 1.499(5) . ?
C8 C11 1.56(2) . ?
C8 C11A 1.501(13) . ?
C9 H9a 0.9800 . ?
C9 H9b 0.9800 . ?
C9 H9c 0.9800 . ?
C10 H10a 0.9800 . ?
C10 H10b 0.9800 . ?
C10 H10c 0.9800 . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 0.9800 . ?
C11A H11d 0.9900 . ?
C11A H11e 0.9900 . ?
C11A B2 1.823(17) . ?
C12 C13 1.402(5) . ?
C12 C17 1.387(6) . ?
C12 B1 1.666(7) . ?
C12 B2 1.879(11) . ?
C13 C14 1.379(5) . ?
C14 C15 1.371(5) . ?
C15 C16 1.377(5) . ?
C16 C17 1.370(5) . ?
C18 C19 1.391(6) . ?
C18 C23 1.392(5) . ?
C18 B1 1.748(7) . ?
C18 B2 1.731(11) . ?
C19 C20 1.377(6) . ?
C20 C21 1.382(6) . ?
C21 C22 1.372(5) . ?
C22 C23 1.375(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C1 110.0(3) . . ?
C4 N1 C1 128.1(3) . . ?
C4 N1 C3 122.0(3) . . ?
C3 N2 C2 109.3(3) . . ?
C8 N2 C2 125.7(3) . . ?
C8 N2 C3 125.0(3) . . ?
H1 C1 N1 126.5(2) . . ?
C2 C1 N1 106.9(3) . . ?
C2 C1 H1 126.5(2) . . ?
C1 C2 N2 107.7(3) . . ?
H2 C2 N2 126.2(2) . . ?
H2 C2 C1 126.2(2) . . ?
N2 C3 N1 106.2(3) . . ?
C5 C4 N1 108.0(3) . . ?
C6 C4 N1 108.4(3) . . ?
C6 C4 C5 111.6(3) . . ?
H5a C5 C4 109.5 . . ?
H5b C5 C4 109.5 . . ?
H5b C5 H5a 109.5 . . ?
H5c C5 C4 109.5 . . ?
H5c C5 H5a 109.5 . . ?
H5c C5 H5b 109.5 . . ?
H6a C6 C4 109.5 . . ?
H6b C6 C4 109.5 . . ?
H6b C6 H6a 109.5 . . ?
H6c C6 C4 109.5 . . ?
H6c C6 H6a 109.5 . . ?
H6c C6 H6b 109.5 . . ?
H7b C7 H7a 108.6 . . ?
B1 C7 H7a 110.4(4) . . ?
B1 C7 H7b 110.4(4) . . ?
H7Ab C7A H7Aa 109.5 . . ?
H7Ac C7A H7Aa 109.5 . . ?
H7Ac C7A H7Ab 109.5 . . ?
C9 C8 N2 107.9(3) . . ?
C10 C8 N2 108.4(3) . . ?
C10 C8 C9 110.9(4) . . ?
H9a C9 C8 109.5 . . ?
H9b C9 C8 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 C8 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
H10a C10 C8 109.5 . . ?
H10b C10 C8 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C8 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
H11e C11A H11d 109.335424404(15) . . ?
B2 C11A H11d 111.5(5) . . ?
B2 C11A H11e 111.5(5) . . ?
C17 C12 C13 113.1(3) . . ?
C12 C13 F1 120.5(3) . . ?
C14 C13 F1 115.4(3) . . ?
C14 C13 C12 124.0(3) . . ?
C13 C14 F2 120.7(3) . . ?
C15 C14 F2 119.9(3) . . ?
C15 C14 C13 119.4(3) . . ?
C14 C15 F3 120.2(3) . . ?
C16 C15 F3 120.3(3) . . ?
C16 C15 C14 119.5(3) . . ?
C15 C16 F4 119.7(3) . . ?
C17 C16 F4 121.1(4) . . ?
C17 C16 C15 119.2(3) . . ?
C12 C17 F5 119.5(4) . . ?
C16 C17 F5 115.6(4) . . ?
C16 C17 C12 124.9(3) . . ?
C23 C18 C19 112.6(4) . . ?
C18 C19 F6 120.0(4) . . ?
C20 C19 F6 115.3(4) . . ?
C20 C19 C18 124.7(4) . . ?
C19 C20 F7 120.6(4) . . ?
C21 C20 F7 119.8(4) . . ?
C21 C20 C19 119.6(4) . . ?
C20 C21 F8 121.0(4) . . ?
C22 C21 F8 120.5(4) . . ?
C22 C21 C20 118.5(3) . . ?
C21 C22 F9 119.5(3) . . ?
C23 C22 F9 120.8(3) . . ?
C23 C22 C21 119.7(3) . . ?
C18 C23 F10 119.5(3) . . ?
C22 C23 F10 115.6(3) . . ?
C22 C23 C18 124.9(4) . . ?
C12 B1 C3 110.8(4) . . ?
C18 B1 C3 105.0(4) . . ?
C18 B1 C12 110.6(4) . . ?
C12 B2 C3 100.0(5) . . ?
C18 B2 C3 104.3(6) . . ?
C18 B2 C12 101.9(5) . . ?

_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_rp003_0ma
_database_code_depnum_ccdc_archive 'CCDC 1035568'
_audit_update_record             
;
2014-11-23 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_formula_sum            'C29 H39 B N2'
_chemical_formula_weight         426.43

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pccn

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

_cell_length_a                   16.756(3)
_cell_length_b                   19.073(4)
_cell_length_c                   15.930(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5091.1(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      24.93

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1856
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45140
_diffrn_reflns_av_R_equivalents  0.1152
_diffrn_reflns_av_sigmaI/netI    0.0699
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4492
_reflns_number_gt                2813
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0724P)²+3.7993P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4492
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1722
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.14841(13) 0.55360(11) 0.29126(14) 0.0305(6) Uani 1 1 d . . .
N2 N 0.13038(12) 0.65086(11) 0.35646(13) 0.0264(5) Uani 1 1 d . . .
C12 C 0.1593(2) 0.32507(16) 0.0591(2) 0.0525(9) Uani 1 1 d . . .
H12A H 0.1413 0.2819 0.0866 0.079 Uiso 1 1 calc R . .
H12B H 0.2146 0.3193 0.0403 0.079 Uiso 1 1 calc R . .
H12C H 0.1251 0.3349 0.0106 0.079 Uiso 1 1 calc R . .
C7 C 0.15456(16) 0.38536(15) 0.1205(2) 0.0376(8) Uani 1 1 d . . .
C8 C 0.17684(16) 0.45258(15) 0.09618(18) 0.0351(7) Uani 1 1 d . . .
H8A H 0.1950 0.4600 0.0404 0.042 Uiso 1 1 calc R . .
C9 C 0.17333(15) 0.50919(14) 0.15072(17) 0.0285(6) Uani 1 1 d . . .
C4 C 0.14655(15) 0.49619(14) 0.23220(17) 0.0295(7) Uani 1 1 d . . .
C1 C 0.09321(15) 0.60562(14) 0.30269(16) 0.0259(6) Uani 1 1 d . . .
C13 C 0.10306(14) 0.71811(13) 0.38636(16) 0.0241(6) Uani 1 1 d . . .
C14 C 0.10629(14) 0.77564(14) 0.33241(16) 0.0260(6) Uani 1 1 d . . .
C15 C 0.08407(15) 0.84025(14) 0.36448(16) 0.0282(6) Uani 1 1 d . . .
H15A H 0.0844 0.8800 0.3285 0.034 Uiso 1 1 calc R . .
C16 C 0.06121(15) 0.84861(14) 0.44798(16) 0.0279(6) Uani 1 1 d . . .
C21 C 0.03772(18) 0.92010(14) 0.48015(18) 0.0383(7) Uani 1 1 d . . .
H21A H 0.0233 0.9167 0.5396 0.057 Uiso 1 1 calc R . .
H21B H -0.0081 0.9375 0.4481 0.057 Uiso 1 1 calc R . .
H21C H 0.0827 0.9525 0.4737 0.057 Uiso 1 1 calc R . .
C6 C 0.12977(16) 0.37527(15) 0.2021(2) 0.0387(8) Uani 1 1 d . . .
H6A H 0.1140 0.3296 0.2190 0.046 Uiso 1 1 calc R . .
C5 C 0.12697(16) 0.42922(15) 0.26043(19) 0.0361(7) Uani 1 1 d . . .
C11 C 0.1081(2) 0.41489(18) 0.3516(2) 0.0536(9) Uani 1 1 d . . .
H11A H 0.0958 0.3650 0.3588 0.080 Uiso 1 1 calc R . .
H11B H 0.0619 0.4430 0.3687 0.080 Uiso 1 1 calc R . .
H11C H 0.1542 0.4273 0.3863 0.080 Uiso 1 1 calc R . .
C10 C 0.20056(18) 0.58110(15) 0.12420(18) 0.0374(7) Uani 1 1 d . . .
H10A H 0.2172 0.5799 0.0652 0.056 Uiso 1 1 calc R . .
H10B H 0.2457 0.5957 0.1592 0.056 Uiso 1 1 calc R . .
H10C H 0.1566 0.6145 0.1309 0.056 Uiso 1 1 calc R . .
B1 B 0.00722(18) 0.61555(16) 0.25474(19) 0.0268(7) Uani 1 1 d . . .
C26 C -0.05938(15) 0.66254(15) 0.30454(18) 0.0326(7) Uani 1 1 d . . .
H26A H -0.0336 0.7069 0.3243 0.039 Uiso 1 1 calc R . .
C27 C -0.12589(17) 0.68124(16) 0.2413(2) 0.0401(8) Uani 1 1 d . . .
H27A H -0.1668 0.7099 0.2702 0.048 Uiso 1 1 calc R . .
H27B H -0.1028 0.7102 0.1958 0.048 Uiso 1 1 calc R . .
C28 C -0.16595(16) 0.61730(16) 0.2028(2) 0.0398(8) Uani 1 1 d . . .
H28A H -0.1978 0.5931 0.2464 0.048 Uiso 1 1 calc R . .
H28B H -0.2030 0.6327 0.1580 0.048 Uiso 1 1 calc R . .
C29 C -0.10579(16) 0.56612(16) 0.16592(18) 0.0380(7) Uani 1 1 d . . .
H29A H -0.0803 0.5879 0.1163 0.046 Uiso 1 1 calc R . .
H29B H -0.1344 0.5237 0.1466 0.046 Uiso 1 1 calc R . .
C22 C -0.04044(16) 0.54425(15) 0.22857(17) 0.0324(7) Uani 1 1 d . . .
H22A H -0.0025 0.5115 0.2000 0.039 Uiso 1 1 calc R . .
C23 C -0.07857(18) 0.50611(16) 0.30493(18) 0.0401(8) Uani 1 1 d . . .
H23A H -0.1360 0.4986 0.2936 0.048 Uiso 1 1 calc R . .
H23B H -0.0533 0.4595 0.3112 0.048 Uiso 1 1 calc R . .
C24 C -0.06967(18) 0.54662(16) 0.38762(18) 0.0418(8) Uani 1 1 d . . .
H24A H -0.1023 0.5233 0.4313 0.050 Uiso 1 1 calc R . .
H24B H -0.0132 0.5445 0.4058 0.050 Uiso 1 1 calc R . .
C25 C -0.09487(17) 0.62337(16) 0.38166(19) 0.0399(8) Uani 1 1 d . . .
H25A H -0.0780 0.6479 0.4335 0.048 Uiso 1 1 calc R . .
H25B H -0.1538 0.6257 0.3787 0.048 Uiso 1 1 calc R . .
C18 C 0.08045(15) 0.72399(14) 0.47014(16) 0.0265(6) Uani 1 1 d . . .
C17 C 0.05939(16) 0.79030(14) 0.49940(16) 0.0295(7) Uani 1 1 d . . .
H17A H 0.0433 0.7956 0.5563 0.035 Uiso 1 1 calc R . .
C19 C 0.07937(19) 0.66115(15) 0.52787(17) 0.0376(7) Uani 1 1 d . . .
H19A H 0.0958 0.6193 0.4966 0.056 Uiso 1 1 calc R . .
H19B H 0.0253 0.6543 0.5498 0.056 Uiso 1 1 calc R . .
H19C H 0.1163 0.6690 0.5746 0.056 Uiso 1 1 calc R . .
C20 C 0.13178(19) 0.76879(16) 0.24218(17) 0.0402(8) Uani 1 1 d . . .
H20A H 0.1301 0.8149 0.2152 0.060 Uiso 1 1 calc R . .
H20B H 0.0956 0.7367 0.2129 0.060 Uiso 1 1 calc R . .
H20C H 0.1863 0.7503 0.2398 0.060 Uiso 1 1 calc R . .
C2 C 0.21727(17) 0.56702(16) 0.33673(18) 0.0401(8) Uani 1 1 d . . .
H2A H 0.2637 0.5385 0.3385 0.048 Uiso 1 1 calc R . .
C3 C 0.20634(16) 0.62716(16) 0.37743(18) 0.0369(7) Uani 1 1 d . . .
H3A H 0.2433 0.6496 0.4138 0.044 Uiso 1 1 calc R . .
H1 H 0.0280(15) 0.6433(13) 0.1935(16) 0.029(7) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.368(3) . ?
N1 C2 1.386(4) . ?
N1 C4 1.444(3) . ?
N2 C1 1.366(3) . ?
N2 C3 1.391(3) . ?
N2 C13 1.443(3) . ?
C12 C7 1.512(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C7 C6 1.377(4) . ?
C7 C8 1.391(4) . ?
C8 C9 1.387(4) . ?
C8 H8A 0.9500 . ?
C9 C4 1.396(4) . ?
C9 C10 1.506(4) . ?
C4 C5 1.394(4) . ?
C1 B1 1.642(4) . ?
C13 C18 1.392(4) . ?
C13 C14 1.395(4) . ?
C14 C15 1.385(4) . ?
C14 C20 1.505(4) . ?
C15 C16 1.393(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.382(4) . ?
C16 C21 1.509(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C6 C5 1.388(4) . ?
C6 H6A 0.9500 . ?
C5 C11 1.511(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
B1 C22 1.631(4) . ?
B1 C26 1.636(4) . ?
B1 H1 1.16(3) . ?
C26 C27 1.544(4) . ?
C26 C25 1.556(4) . ?
C26 H26A 1.0000 . ?
C27 C28 1.521(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.521(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C22 1.539(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C22 C23 1.555(4) . ?
C22 H22A 1.0000 . ?
C23 C24 1.534(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.527(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C18 C17 1.393(4) . ?
C18 C19 1.511(4) . ?
C17 H17A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C2 C3 1.330(4) . ?
C2 H2A 0.9500 . ?
C3 H3A 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 C2 111.1(2) . . ?
C1 N1 C4 128.5(2) . . ?
C2 N1 C4 119.9(2) . . ?
C1 N2 C3 111.2(2) . . ?
C1 N2 C13 128.6(2) . . ?
C3 N2 C13 120.0(2) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C7 C8 118.2(3) . . ?
C6 C7 C12 121.3(3) . . ?
C8 C7 C12 120.4(3) . . ?
C9 C8 C7 122.1(3) . . ?
C9 C8 H8A 118.9 . . ?
C7 C8 H8A 118.9 . . ?
C8 C9 C4 117.3(3) . . ?
C8 C9 C10 121.4(3) . . ?
C4 C9 C10 121.3(2) . . ?
C5 C4 C9 122.6(2) . . ?
C5 C4 N1 119.3(2) . . ?
C9 C4 N1 117.7(2) . . ?
N2 C1 N1 103.5(2) . . ?
N2 C1 B1 128.2(2) . . ?
N1 C1 B1 127.9(2) . . ?
C18 C13 C14 122.5(2) . . ?
C18 C13 N2 118.3(2) . . ?
C14 C13 N2 118.9(2) . . ?
C15 C14 C13 117.5(2) . . ?
C15 C14 C20 120.4(2) . . ?
C13 C14 C20 122.1(2) . . ?
C14 C15 C16 121.9(2) . . ?
C14 C15 H15A 119.1 . . ?
C16 C15 H15A 119.1 . . ?
C17 C16 C15 118.7(2) . . ?
C17 C16 C21 121.4(2) . . ?
C15 C16 C21 120.0(2) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C7 C6 C5 122.6(3) . . ?
C7 C6 H6A 118.7 . . ?
C5 C6 H6A 118.7 . . ?
C6 C5 C4 117.1(3) . . ?
C6 C5 C11 121.1(3) . . ?
C4 C5 C11 121.7(3) . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C22 B1 C26 104.3(2) . . ?
C22 B1 C1 116.9(2) . . ?
C26 B1 C1 115.9(2) . . ?
C22 B1 H1 108.1(12) . . ?
C26 B1 H1 111.2(12) . . ?
C1 B1 H1 100.4(12) . . ?
C27 C26 C25 110.5(2) . . ?
C27 C26 B1 107.6(2) . . ?
C25 C26 B1 112.4(2) . . ?
C27 C26 H26A 108.8 . . ?
C25 C26 H26A 108.8 . . ?
B1 C26 H26A 108.8 . . ?
C28 C27 C26 113.4(2) . . ?
C28 C27 H27A 108.9 . . ?
C26 C27 H27A 108.9 . . ?
C28 C27 H27B 108.9 . . ?
C26 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
C29 C28 C27 112.2(2) . . ?
C29 C28 H28A 109.2 . . ?
C27 C28 H28A 109.2 . . ?
C29 C28 H28B 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C28 C29 C22 113.3(2) . . ?
C28 C29 H29A 108.9 . . ?
C22 C29 H29A 108.9 . . ?
C28 C29 H29B 108.9 . . ?
C22 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
C29 C22 C23 110.0(2) . . ?
C29 C22 B1 106.7(2) . . ?
C23 C22 B1 113.0(2) . . ?
C29 C22 H22A 109.0 . . ?
C23 C22 H22A 109.0 . . ?
B1 C22 H22A 109.0 . . ?
C24 C23 C22 113.3(2) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C23 113.7(3) . . ?
C25 C24 H24A 108.8 . . ?
C23 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C24 C25 C26 113.8(2) . . ?
C24 C25 H25A 108.8 . . ?
C26 C25 H25A 108.8 . . ?
C24 C25 H25B 108.8 . . ?
C26 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C13 C18 C17 117.6(2) . . ?
C13 C18 C19 121.5(2) . . ?
C17 C18 C19 120.9(2) . . ?
C16 C17 C18 121.8(2) . . ?
C16 C17 H17A 119.1 . . ?
C18 C17 H17A 119.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C2 N1 107.4(2) . . ?
C3 C2 H2A 126.3 . . ?
N1 C2 H2A 126.3 . . ?
C2 C3 N2 106.8(2) . . ?
C2 C3 H3A 126.6 . . ?
N2 C3 H3A 126.6 . . ?

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
C6 C7 C8 C9 -1.2(4) . . . . ?
C12 C7 C8 C9 -180.0(3) . . . . ?
C7 C8 C9 C4 0.2(4) . . . . ?
C7 C8 C9 C10 177.7(3) . . . . ?
C8 C9 C4 C5 2.7(4) . . . . ?
C10 C9 C4 C5 -174.8(3) . . . . ?
C8 C9 C4 N1 175.4(2) . . . . ?
C10 C9 C4 N1 -2.1(4) . . . . ?
C1 N1 C4 C5 -103.4(3) . . . . ?
C2 N1 C4 C5 86.4(3) . . . . ?
C1 N1 C4 C9 83.7(3) . . . . ?
C2 N1 C4 C9 -86.6(3) . . . . ?
C3 N2 C1 N1 0.0(3) . . . . ?
C13 N2 C1 N1 175.2(2) . . . . ?
C3 N2 C1 B1 -173.8(2) . . . . ?
C13 N2 C1 B1 1.5(4) . . . . ?
C2 N1 C1 N2 -0.1(3) . . . . ?
C4 N1 C1 N2 -171.1(2) . . . . ?
C2 N1 C1 B1 173.7(2) . . . . ?
C4 N1 C1 B1 2.7(4) . . . . ?
C1 N2 C13 C18 109.7(3) . . . . ?
C3 N2 C13 C18 -75.4(3) . . . . ?
C1 N2 C13 C14 -75.3(3) . . . . ?
C3 N2 C13 C14 99.6(3) . . . . ?
C18 C13 C14 C15 -1.5(4) . . . . ?
N2 C13 C14 C15 -176.3(2) . . . . ?
C18 C13 C14 C20 179.2(2) . . . . ?
N2 C13 C14 C20 4.5(4) . . . . ?
C13 C14 C15 C16 1.6(4) . . . . ?
C20 C14 C15 C16 -179.1(2) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C14 C15 C16 C21 179.8(2) . . . . ?
C8 C7 C6 C5 -0.6(4) . . . . ?
C12 C7 C6 C5 178.1(3) . . . . ?
C7 C6 C5 C4 3.3(4) . . . . ?
C7 C6 C5 C11 -173.3(3) . . . . ?
C9 C4 C5 C6 -4.4(4) . . . . ?
N1 C4 C5 C6 -177.0(2) . . . . ?
C9 C4 C5 C11 172.2(3) . . . . ?
N1 C4 C5 C11 -0.4(4) . . . . ?
N2 C1 B1 C22 -154.1(2) . . . . ?
N1 C1 B1 C22 33.6(4) . . . . ?
N2 C1 B1 C26 -30.5(4) . . . . ?
N1 C1 B1 C26 157.2(3) . . . . ?
C22 B1 C26 C27 -64.2(3) . . . . ?
C1 B1 C26 C27 165.9(2) . . . . ?
C22 B1 C26 C25 57.7(3) . . . . ?
C1 B1 C26 C25 -72.3(3) . . . . ?
C25 C26 C27 C28 -64.2(3) . . . . ?
B1 C26 C27 C28 58.8(3) . . . . ?
C26 C27 C28 C29 -51.9(4) . . . . ?
C27 C28 C29 C22 53.4(3) . . . . ?
C28 C29 C22 C23 61.7(3) . . . . ?
C28 C29 C22 B1 -61.2(3) . . . . ?
C26 B1 C22 C29 65.1(3) . . . . ?
C1 B1 C22 C29 -165.5(2) . . . . ?
C26 B1 C22 C23 -55.9(3) . . . . ?
C1 B1 C22 C23 73.4(3) . . . . ?
C29 C22 C23 C24 -114.2(3) . . . . ?
B1 C22 C23 C24 5.0(4) . . . . ?
C22 C23 C24 C25 49.7(3) . . . . ?
C23 C24 C25 C26 -47.9(3) . . . . ?
C27 C26 C25 C24 111.9(3) . . . . ?
B1 C26 C25 C24 -8.2(3) . . . . ?
C14 C13 C18 C17 0.9(4) . . . . ?
N2 C13 C18 C17 175.7(2) . . . . ?
C14 C13 C18 C19 -178.5(2) . . . . ?
N2 C13 C18 C19 -3.7(4) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
C21 C16 C17 C18 179.6(2) . . . . ?
C13 C18 C17 C16 -0.5(4) . . . . ?
C19 C18 C17 C16 179.0(2) . . . . ?
C1 N1 C2 C3 0.2(3) . . . . ?
C4 N1 C2 C3 172.1(2) . . . . ?
N1 C2 C3 N2 -0.2(3) . . . . ?
C1 N2 C3 C2 0.2(3) . . . . ?
C13 N2 C3 C2 -175.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_rp004_0m
_database_code_depnum_ccdc_archive 'CCDC 1035569'
_audit_update_record             
;
2014-11-23 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_formula_sum            'C18 H25 B N2'
_chemical_formula_weight         280.21

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   8.4021(11)
_cell_length_b                   10.0498(13)
_cell_length_c                   9.2882(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.645(6)
_cell_angle_gamma                90.00
_cell_volume                     782.70(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4626
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.41

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5875
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2760
_reflns_number_gt                2597
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0572P)²+0.3365P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         2760
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.1031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.37739(19) 0.61386(17) 0.92930(17) 0.0186(4) Uani 1 1 d . . .
N1 N 0.3070(2) 0.48905(19) 1.10075(17) 0.0204(4) Uani 1 1 d . . .
C8 C 0.4516(3) 0.7832(2) 0.5256(2) 0.0284(5) Uani 1 1 d . . .
H8A H 0.4678 0.8214 0.4341 0.034 Uiso 1 1 calc R . .
C9 C 0.5336(3) 0.6692(2) 0.5691(2) 0.0263(5) Uani 1 1 d . . .
H9A H 0.6066 0.6300 0.5076 0.032 Uiso 1 1 calc R . .
C10 C 0.5098(2) 0.6119(2) 0.7021(2) 0.0227(4) Uani 1 1 d . . .
H10A H 0.5661 0.5337 0.7322 0.027 Uiso 1 1 calc R . .
C5 C 0.4027(2) 0.6706(2) 0.7902(2) 0.0183(4) Uani 1 1 d . . .
C1 C 0.2965(2) 0.4991(2) 0.9551(2) 0.0168(4) Uani 1 1 d . . .
C11 C 0.1387(2) 0.2605(2) 0.8717(2) 0.0198(4) Uani 1 1 d . . .
H11A H 0.2043 0.2151 0.9508 0.024 Uiso 1 1 calc R . .
C12 C -0.0312(2) 0.2859(2) 0.9226(2) 0.0260(5) Uani 1 1 d . . .
H12A H -0.1078 0.2289 0.8656 0.031 Uiso 1 1 calc R . .
H12B H -0.0333 0.2589 1.0249 0.031 Uiso 1 1 calc R . .
C13 C -0.0857(3) 0.4287(3) 0.9085(3) 0.0369(6) Uani 1 1 d . . .
H13A H -0.0281 0.4817 0.9851 0.044 Uiso 1 1 calc R . .
H13B H -0.2007 0.4326 0.9256 0.044 Uiso 1 1 calc R . .
C7 C 0.3456(3) 0.8421(2) 0.6151(2) 0.0286(5) Uani 1 1 d . . .
H7A H 0.2897 0.9205 0.5850 0.034 Uiso 1 1 calc R . .
C6 C 0.3216(3) 0.7860(2) 0.7486(2) 0.0248(5) Uani 1 1 d . . .
H6A H 0.2502 0.8262 0.8109 0.030 Uiso 1 1 calc R . .
C3 C 0.4380(2) 0.6720(2) 1.0570(2) 0.0253(5) Uani 1 1 d . . .
H3A H 0.4987 0.7516 1.0667 0.030 Uiso 1 1 calc R . .
C2 C 0.3936(3) 0.5934(2) 1.1635(2) 0.0279(5) Uani 1 1 d . . .
H2A H 0.4172 0.6068 1.2638 0.034 Uiso 1 1 calc R . .
C4 C 0.2340(3) 0.3871(2) 1.1885(2) 0.0290(5) Uani 1 1 d . . .
H4A H 0.1779 0.3221 1.1250 0.043 Uiso 1 1 calc R . .
H4B H 0.1580 0.4293 1.2501 0.043 Uiso 1 1 calc R . .
H4C H 0.3172 0.3419 1.2489 0.043 Uiso 1 1 calc R . .
C14 C -0.0605(2) 0.4938(2) 0.7628(2) 0.0247(5) Uani 1 1 d . . .
H14A H -0.0763 0.5910 0.7718 0.030 Uiso 1 1 calc R . .
H14B H -0.1428 0.4601 0.6909 0.030 Uiso 1 1 calc R . .
C15 C 0.1068(2) 0.4685(2) 0.7051(2) 0.0181(4) Uani 1 1 d . . .
H15A H 0.1531 0.5556 0.6768 0.022 Uiso 1 1 calc R . .
C16 C 0.0961(3) 0.3756(2) 0.5722(2) 0.0226(5) Uani 1 1 d . . .
H16A H 0.0212 0.4150 0.4973 0.027 Uiso 1 1 calc R . .
H16B H 0.2023 0.3707 0.5322 0.027 Uiso 1 1 calc R . .
C17 C 0.0405(3) 0.2344(2) 0.6052(2) 0.0279(5) Uani 1 1 d . . .
H17A H 0.0536 0.1777 0.5196 0.033 Uiso 1 1 calc R . .
H17B H -0.0745 0.2369 0.6225 0.033 Uiso 1 1 calc R . .
C18 C 0.1313(3) 0.1711(2) 0.7362(2) 0.0262(5) Uani 1 1 d . . .
H18A H 0.2414 0.1506 0.7110 0.031 Uiso 1 1 calc R . .
H18B H 0.0791 0.0860 0.7590 0.031 Uiso 1 1 calc R . .
B1 B 0.2290(3) 0.3980(2) 0.8274(2) 0.0160(4) Uani 1 1 d . . .
H1 H 0.3241 0.3695 0.7758 0.019 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C1 1.368(3) . ?
N2 C3 1.390(3) . ?
N2 C5 1.440(2) . ?
N1 C1 1.354(2) . ?
N1 C2 1.384(3) . ?
N1 C4 1.468(3) . ?
C8 C9 1.384(3) . ?
C8 C7 1.388(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.389(3) . ?
C9 H9A 0.9500 . ?
C10 C5 1.386(3) . ?
C10 H10A 0.9500 . ?
C5 C6 1.387(3) . ?
C1 B1 1.635(3) . ?
C11 C18 1.544(3) . ?
C11 C12 1.553(3) . ?
C11 B1 1.642(3) . ?
C11 H11A 1.0000 . ?
C12 C13 1.509(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.530(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C7 C6 1.389(3) . ?
C7 H7A 0.9500 . ?
C6 H6A 0.9500 . ?
C3 C2 1.337(3) . ?
C3 H3A 0.9500 . ?
C2 H2A 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C14 C15 1.556(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.545(3) . ?
C15 B1 1.643(3) . ?
C15 H15A 1.0000 . ?
C16 C17 1.531(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.533(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
B1 H1 1.0000 . ?

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 N2 C3 111.39(17) . . ?
C1 N2 C5 126.48(16) . . ?
C3 N2 C5 122.12(17) . . ?
C1 N1 C2 111.30(18) . . ?
C1 N1 C4 127.14(18) . . ?
C2 N1 C4 121.51(17) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C5 C10 C9 119.0(2) . . ?
C5 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
C10 C5 C6 121.14(19) . . ?
C10 C5 N2 119.98(19) . . ?
C6 C5 N2 118.86(18) . . ?
N1 C1 N2 103.66(17) . . ?
N1 C1 B1 132.54(18) . . ?
N2 C1 B1 123.37(16) . . ?
C18 C11 C12 110.73(17) . . ?
C18 C11 B1 106.34(16) . . ?
C12 C11 B1 112.68(17) . . ?
C18 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
B1 C11 H11A 109.0 . . ?
C13 C12 C11 114.20(18) . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 115.1(2) . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C8 C7 C6 119.8(2) . . ?
C8 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C5 C6 C7 119.4(2) . . ?
C5 C6 H6A 120.3 . . ?
C7 C6 H6A 120.3 . . ?
C2 C3 N2 106.15(19) . . ?
C2 C3 H3A 126.9 . . ?
N2 C3 H3A 126.9 . . ?
C3 C2 N1 107.49(18) . . ?
C3 C2 H2A 126.3 . . ?
N1 C2 H2A 126.3 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C13 C14 C15 114.44(17) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 111.45(16) . . ?
C16 C15 B1 107.10(16) . . ?
C14 C15 B1 111.74(15) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
B1 C15 H15A 108.8 . . ?
C17 C16 C15 113.78(17) . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 C18 113.65(18) . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C11 113.42(18) . . ?
C17 C18 H18A 108.9 . . ?
C11 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C11 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C1 B1 C11 119.08(16) . . ?
C1 B1 C15 113.99(16) . . ?
C11 B1 C15 104.93(16) . . ?
C1 B1 H1 106.0 . . ?
C11 B1 H1 106.0 . . ?
C15 B1 H1 106.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C5 0.0(3) . . . . ?
C9 C10 C5 C6 -1.0(3) . . . . ?
C9 C10 C5 N2 -179.31(18) . . . . ?
C1 N2 C5 C10 -73.0(3) . . . . ?
C3 N2 C5 C10 105.9(2) . . . . ?
C1 N2 C5 C6 108.7(2) . . . . ?
C3 N2 C5 C6 -72.5(3) . . . . ?
C2 N1 C1 N2 -0.8(2) . . . . ?
C4 N1 C1 N2 176.78(18) . . . . ?
C2 N1 C1 B1 171.64(19) . . . . ?
C4 N1 C1 B1 -10.8(3) . . . . ?
C3 N2 C1 N1 0.7(2) . . . . ?
C5 N2 C1 N1 179.71(18) . . . . ?
C3 N2 C1 B1 -172.58(18) . . . . ?
C5 N2 C1 B1 6.4(3) . . . . ?
C18 C11 C12 C13 -113.6(2) . . . . ?
B1 C11 C12 C13 5.4(3) . . . . ?
C11 C12 C13 C14 47.8(3) . . . . ?
C9 C8 C7 C6 -0.2(3) . . . . ?
C10 C5 C6 C7 1.3(3) . . . . ?
N2 C5 C6 C7 179.67(18) . . . . ?
C8 C7 C6 C5 -0.7(3) . . . . ?
C1 N2 C3 C2 -0.4(2) . . . . ?
C5 N2 C3 C2 -179.45(18) . . . . ?
N2 C3 C2 N1 -0.1(2) . . . . ?
C1 N1 C2 C3 0.6(2) . . . . ?
C4 N1 C2 C3 -177.17(18) . . . . ?
C12 C13 C14 C15 -45.6(3) . . . . ?
C13 C14 C15 C16 110.2(2) . . . . ?
C13 C14 C15 B1 -9.6(3) . . . . ?
C14 C15 C16 C17 -65.1(2) . . . . ?
B1 C15 C16 C17 57.4(2) . . . . ?
C15 C16 C17 C18 -49.4(2) . . . . ?
C16 C17 C18 C11 50.7(3) . . . . ?
C12 C11 C18 C17 63.1(2) . . . . ?
B1 C11 C18 C17 -59.6(2) . . . . ?
N1 C1 B1 C11 6.8(3) . . . . ?
N2 C1 B1 C11 177.98(17) . . . . ?
N1 C1 B1 C15 131.6(2) . . . . ?
N2 C1 B1 C15 -57.3(2) . . . . ?
C18 C11 B1 C1 -164.92(17) . . . . ?
C12 C11 B1 C1 73.6(2) . . . . ?
C18 C11 B1 C15 66.05(19) . . . . ?
C12 C11 B1 C15 -55.4(2) . . . . ?
C16 C15 B1 C1 162.90(15) . . . . ?
C14 C15 B1 C1 -74.8(2) . . . . ?
C16 C15 B1 C11 -65.09(19) . . . . ?
C14 C15 B1 C11 57.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_roy001_0m
_database_code_depnum_ccdc_archive 'CCDC 1035570'
_audit_update_record             
;
2014-11-23 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_formula_sum            'C13 H23 B N2'
_chemical_formula_weight         218.14

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   9.2454(5)
_cell_length_b                   7.0797(4)
_cell_length_c                   9.5352(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.812(2)
_cell_angle_gamma                90.00
_cell_volume                     613.04(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4726
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      27.51

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9732
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5558
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         27.51
_reflns_number_total             2721
_reflns_number_gt                2636
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0796P)²+0.1747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         2721
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.37731(15) 0.4419(2) -0.00951(14) 0.0197(3) Uani 1 1 d . . .
C10 C 0.33878(17) 0.5266(2) 0.38719(16) 0.0154(3) Uani 1 1 d . . .
H10A H 0.4452 0.5604 0.4161 0.018 Uiso 1 1 calc R . .
N2 N 0.56345(14) 0.4375(2) 0.16178(14) 0.0187(3) Uani 1 1 d . . .
C1 C 0.41482(16) 0.4222(2) 0.13426(16) 0.0163(3) Uani 1 1 d . . .
B1 B 0.32103(18) 0.3699(2) 0.25785(17) 0.0146(3) Uani 1 1 d . . .
H1 H 0.3642 0.2498 0.3026 0.018 Uiso 1 1 calc R . .
C9 C 0.24894(18) 0.7099(2) 0.34222(18) 0.0192(3) Uani 1 1 d . . .
H9A H 0.1874 0.7379 0.4141 0.023 Uiso 1 1 calc R . .
H9B H 0.3184 0.8164 0.3424 0.023 Uiso 1 1 calc R . .
C8 C 0.14934(18) 0.6978(2) 0.19476(18) 0.0212(3) Uani 1 1 d . . .
H8A H 0.2114 0.7006 0.1207 0.025 Uiso 1 1 calc R . .
H8B H 0.0843 0.8100 0.1807 0.025 Uiso 1 1 calc R . .
C12 C 0.12778(19) 0.3599(2) 0.47908(17) 0.0216(3) Uani 1 1 d . . .
H12A H 0.1066 0.2853 0.5607 0.026 Uiso 1 1 calc R . .
H12B H 0.0606 0.4700 0.4662 0.026 Uiso 1 1 calc R . .
C11 C 0.28718(17) 0.4304(3) 0.51431(16) 0.0202(3) Uani 1 1 d . . .
H11A H 0.3528 0.3220 0.5464 0.024 Uiso 1 1 calc R . .
H11B H 0.2967 0.5212 0.5944 0.024 Uiso 1 1 calc R . .
C6 C 0.14289(17) 0.3337(2) 0.21355(16) 0.0167(3) Uani 1 1 d . . .
H6A H 0.1230 0.2454 0.1303 0.020 Uiso 1 1 calc R . .
C7 C 0.05390(17) 0.5190(3) 0.17474(17) 0.0206(3) Uani 1 1 d . . .
H7A H 0.0026 0.5118 0.0740 0.025 Uiso 1 1 calc R . .
H7B H -0.0221 0.5290 0.2350 0.025 Uiso 1 1 calc R . .
C13 C 0.09670(18) 0.2378(2) 0.34416(17) 0.0195(3) Uani 1 1 d . . .
H13A H -0.0099 0.2091 0.3211 0.023 Uiso 1 1 calc R . .
H13B H 0.1502 0.1167 0.3634 0.023 Uiso 1 1 calc R . .
C2 C 0.5012(2) 0.4670(3) -0.07022(18) 0.0251(4) Uani 1 1 d . . .
H2A H 0.5032 0.4833 -0.1688 0.030 Uiso 1 1 calc R . .
C3 C 0.61752(19) 0.4639(3) 0.0372(2) 0.0255(4) Uani 1 1 d . . .
H3A H 0.7180 0.4772 0.0295 0.031 Uiso 1 1 calc R . .
C5 C 0.65788(17) 0.4159(3) 0.30226(18) 0.0242(4) Uani 1 1 d . . .
H5A H 0.5965 0.3987 0.3747 0.036 Uiso 1 1 calc R . .
H5B H 0.7187 0.5292 0.3246 0.036 Uiso 1 1 calc R . .
H5C H 0.7216 0.3055 0.3016 0.036 Uiso 1 1 calc R . .
C4 C 0.22894(18) 0.4332(3) -0.09581(16) 0.0281(4) Uani 1 1 d . . .
H4A H 0.1573 0.4141 -0.0333 0.042 Uiso 1 1 calc R . .
H4B H 0.2229 0.3278 -0.1633 0.042 Uiso 1 1 calc R . .
H4C H 0.2072 0.5517 -0.1487 0.042 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.357(2) . ?
N1 C2 1.389(2) . ?
N1 C4 1.463(2) . ?
C10 C11 1.542(2) . ?
C10 C9 1.557(2) . ?
C10 B1 1.644(2) . ?
C10 H10A 1.0000 . ?
N2 C1 1.354(2) . ?
N2 C3 1.385(2) . ?
N2 C5 1.463(2) . ?
C1 B1 1.631(2) . ?
B1 C6 1.642(2) . ?
B1 H1 1.0000 . ?
C9 C8 1.532(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8 C7 1.534(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C12 C13 1.531(2) . ?
C12 C11 1.532(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C6 C13 1.547(2) . ?
C6 C7 1.556(2) . ?
C6 H6A 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C2 C3 1.339(3) . ?
C2 H2A 0.9500 . ?
C3 H3A 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 111.09(14) . . ?
C1 N1 C4 126.81(13) . . ?
C2 N1 C4 122.07(14) . . ?
C11 C10 C9 110.92(12) . . ?
C11 C10 B1 106.82(13) . . ?
C9 C10 B1 112.51(12) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
B1 C10 H10A 108.8 . . ?
C1 N2 C3 111.16(14) . . ?
C1 N2 C5 125.36(13) . . ?
C3 N2 C5 123.34(14) . . ?
N2 C1 N1 104.21(13) . . ?
N2 C1 B1 122.39(13) . . ?
N1 C1 B1 133.12(13) . . ?
C1 B1 C6 119.55(12) . . ?
C1 B1 C10 113.38(13) . . ?
C6 B1 C10 104.63(12) . . ?
C1 B1 H1 106.1 . . ?
C6 B1 H1 106.1 . . ?
C10 B1 H1 106.1 . . ?
C8 C9 C10 113.82(13) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C8 C7 113.15(13) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C13 C12 C11 112.90(13) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 C11 C10 113.47(12) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C13 C6 C7 110.35(12) . . ?
C13 C6 B1 106.05(12) . . ?
C7 C6 B1 112.92(13) . . ?
C13 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
B1 C6 H6A 109.1 . . ?
C8 C7 C6 113.58(12) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C12 C13 C6 113.10(13) . . ?
C12 C13 H13A 109.0 . . ?
C6 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C6 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C3 C2 N1 106.60(14) . . ?
C3 C2 H2A 126.7 . . ?
N1 C2 H2A 126.7 . . ?
C2 C3 N2 106.94(15) . . ?
C2 C3 H3A 126.5 . . ?
N2 C3 H3A 126.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 N1 -0.72(19) . . . . ?
C5 N2 C1 N1 -176.61(15) . . . . ?
C3 N2 C1 B1 173.90(14) . . . . ?
C5 N2 C1 B1 -2.0(2) . . . . ?
C2 N1 C1 N2 0.61(19) . . . . ?
C4 N1 C1 N2 178.75(17) . . . . ?
C2 N1 C1 B1 -173.17(16) . . . . ?
C4 N1 C1 B1 5.0(3) . . . . ?
N2 C1 B1 C6 -174.08(15) . . . . ?
N1 C1 B1 C6 -1.2(3) . . . . ?
N2 C1 B1 C10 61.76(19) . . . . ?
N1 C1 B1 C10 -125.39(18) . . . . ?
C11 C10 B1 C1 -162.52(12) . . . . ?
C9 C10 B1 C1 75.54(16) . . . . ?
C11 C10 B1 C6 65.55(15) . . . . ?
C9 C10 B1 C6 -56.39(16) . . . . ?
C11 C10 C9 C8 -112.80(15) . . . . ?
B1 C10 C9 C8 6.79(18) . . . . ?
C10 C9 C8 C7 49.40(18) . . . . ?
C13 C12 C11 C10 51.2(2) . . . . ?
C9 C10 C11 C12 64.23(18) . . . . ?
B1 C10 C11 C12 -58.71(17) . . . . ?
C1 B1 C6 C13 165.44(13) . . . . ?
C10 B1 C6 C13 -66.28(15) . . . . ?
C1 B1 C6 C7 -73.59(17) . . . . ?
C10 B1 C6 C7 54.69(16) . . . . ?
C9 C8 C7 C6 -51.19(18) . . . . ?
C13 C6 C7 C8 114.89(15) . . . . ?
B1 C6 C7 C8 -3.60(18) . . . . ?
C11 C12 C13 C6 -52.29(19) . . . . ?
C7 C6 C13 C12 -62.00(17) . . . . ?
B1 C6 C13 C12 60.61(16) . . . . ?
C1 N1 C2 C3 -0.3(2) . . . . ?
C4 N1 C2 C3 -178.53(17) . . . . ?
N1 C2 C3 N2 -0.2(2) . . . . ?
C1 N2 C3 C2 0.6(2) . . . . ?
C5 N2 C3 C2 176.56(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_jf050_0m
_database_code_depnum_ccdc_archive 'CCDC 1035571'
_audit_update_record             
;
2014-11-23 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_formula_sum            'C15 H27 B N2'
_chemical_formula_weight         246.20

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.4085(6)
_cell_length_b                   9.5348(6)
_cell_length_c                   20.4481(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.479(3)
_cell_angle_gamma                90.00
_cell_volume                     1432.14(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6272
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10530
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2524
_reflns_number_gt                2121
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0460P)²+0.4690P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2524
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.21531(14) 0.61873(11) 0.29253(5) 0.0192(3) Uani 1 1 d . . .
N2 N 0.37399(14) 0.73897(11) 0.23275(5) 0.0195(3) Uani 1 1 d . . .
C6 C -0.06701(18) 0.55959(17) 0.21408(7) 0.0322(4) Uani 1 1 d . . .
H6A H -0.1194 0.5851 0.1692 0.048 Uiso 1 1 calc R . .
H6B H -0.1494 0.5893 0.2453 0.048 Uiso 1 1 calc R . .
H6C H -0.0502 0.4577 0.2169 0.048 Uiso 1 1 calc R . .
C3 C 0.11211(17) 0.63042(14) 0.23064(6) 0.0217(3) Uani 1 1 d . . .
C1 C 0.37752(17) 0.68592(12) 0.29460(6) 0.0184(3) Uani 1 1 d . . .
C12 C 0.61349(17) 0.86585(13) 0.36629(6) 0.0212(3) Uani 1 1 d . . .
H12 H 0.6141 0.9153 0.3232 0.025 Uiso 1 1 calc R . .
C13 C 0.80897(17) 0.86422(14) 0.40290(7) 0.0245(3) Uani 1 1 d . . .
H13A H 0.8910 0.8212 0.3740 0.029 Uiso 1 1 calc R . .
H13B H 0.8497 0.9620 0.4119 0.029 Uiso 1 1 calc R . .
C14 C 0.82573(18) 0.78363(14) 0.46785(7) 0.0261(3) Uani 1 1 d . . .
H14A H 0.7649 0.8378 0.5000 0.031 Uiso 1 1 calc R . .
H14B H 0.9562 0.7755 0.4856 0.031 Uiso 1 1 calc R . .
C2 C 0.21233(18) 0.70736(13) 0.19319(6) 0.0220(3) Uani 1 1 d . . .
C5 C 0.1751(2) 0.75478(16) 0.12333(7) 0.0306(3) Uani 1 1 d . . .
H5A H 0.0488 0.7328 0.1059 0.046 Uiso 1 1 calc R . .
H5B H 0.2576 0.7065 0.0970 0.046 Uiso 1 1 calc R . .
H5C H 0.1945 0.8563 0.1212 0.046 Uiso 1 1 calc R . .
C7 C 0.14978(18) 0.54076(14) 0.34615(7) 0.0254(3) Uani 1 1 d . . .
H7A H 0.2442 0.5397 0.3845 0.038 Uiso 1 1 calc R . .
H7B H 0.1212 0.4443 0.3318 0.038 Uiso 1 1 calc R . .
H7C H 0.0399 0.5859 0.3582 0.038 Uiso 1 1 calc R . .
C8 C 0.54606(17) 0.63404(13) 0.42527(6) 0.0202(3) Uani 1 1 d . . .
H8 H 0.5035 0.5346 0.4205 0.024 Uiso 1 1 calc R . .
C9 C 0.41762(18) 0.71714(14) 0.46605(6) 0.0235(3) Uani 1 1 d . . .
H9A H 0.3172 0.6548 0.4753 0.028 Uiso 1 1 calc R . .
H9B H 0.4869 0.7444 0.5089 0.028 Uiso 1 1 calc R . .
C10 C 0.33651(18) 0.84897(14) 0.43122(7) 0.0247(3) Uani 1 1 d . . .
H10A H 0.2702 0.9026 0.4620 0.030 Uiso 1 1 calc R . .
H10B H 0.2475 0.8209 0.3931 0.030 Uiso 1 1 calc R . .
C11 C 0.48084(18) 0.94382(14) 0.40695(7) 0.0246(3) Uani 1 1 d . . .
H11A H 0.5526 0.9886 0.4456 0.029 Uiso 1 1 calc R . .
H11B H 0.4187 1.0192 0.3793 0.029 Uiso 1 1 calc R . .
C15 C 0.74251(18) 0.63663(14) 0.46125(7) 0.0245(3) Uani 1 1 d . . .
H15A H 0.7430 0.5961 0.5059 0.029 Uiso 1 1 calc R . .
H15B H 0.8199 0.5764 0.4369 0.029 Uiso 1 1 calc R . .
C4 C 0.52379(19) 0.81176(14) 0.20723(7) 0.0261(3) Uani 1 1 d . . .
H4A H 0.4958 0.9121 0.2030 0.039 Uiso 1 1 calc R . .
H4B H 0.5400 0.7734 0.1639 0.039 Uiso 1 1 calc R . .
H4C H 0.6360 0.7987 0.2377 0.039 Uiso 1 1 calc R . .
B1 B 0.5531(2) 0.70125(15) 0.35162(7) 0.0194(3) Uani 1 1 d . . .
H1 H 0.6675(18) 0.6461(15) 0.3276(7) 0.025(4) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3577(16) . ?
N1 C3 1.3952(16) . ?
N1 C7 1.4590(16) . ?
N2 C1 1.3592(16) . ?
N2 C2 1.3883(17) . ?
N2 C4 1.4616(16) . ?
C6 C3 1.4883(19) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C3 C2 1.3505(19) . ?
C1 B1 1.6366(19) . ?
C12 C13 1.5414(18) . ?
C12 C11 1.5563(18) . ?
C12 B1 1.6487(19) . ?
C12 H12 1.0000 . ?
C13 C14 1.5253(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5301(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C2 C5 1.4894(19) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C15 1.5431(18) . ?
C8 C9 1.5605(18) . ?
C8 B1 1.6439(18) . ?
C8 H8 1.0000 . ?
C9 C10 1.5287(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5316(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
B1 H1 1.159(14) . ?

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 C3 111.64(10) . . ?
C1 N1 C7 126.64(11) . . ?
C3 N1 C7 121.71(11) . . ?
C1 N2 C2 111.84(11) . . ?
C1 N2 C4 125.82(11) . . ?
C2 N2 C4 122.19(11) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C3 N1 106.32(11) . . ?
C2 C3 C6 131.08(13) . . ?
N1 C3 C6 122.50(12) . . ?
N1 C1 N2 103.70(11) . . ?
N1 C1 B1 133.05(11) . . ?
N2 C1 B1 123.16(11) . . ?
C13 C12 C11 111.35(11) . . ?
C13 C12 B1 107.11(10) . . ?
C11 C12 B1 112.13(10) . . ?
C13 C12 H12 108.7 . . ?
C11 C12 H12 108.7 . . ?
B1 C12 H12 108.7 . . ?
C14 C13 C12 113.13(11) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 113.48(11) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C3 C2 N2 106.48(11) . . ?
C3 C2 C5 131.45(13) . . ?
N2 C2 C5 122.07(12) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C15 C8 C9 109.88(10) . . ?
C15 C8 B1 106.86(10) . . ?
C9 C8 B1 112.71(10) . . ?
C15 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
B1 C8 H8 109.1 . . ?
C10 C9 C8 113.49(10) . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 112.82(11) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 114.02(11) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C14 C15 C8 113.63(11) . . ?
C14 C15 H15A 108.8 . . ?
C8 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C8 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 B1 C8 120.05(11) . . ?
C1 B1 C12 112.73(10) . . ?
C8 B1 C12 104.15(10) . . ?
C1 B1 H1 102.4(7) . . ?
C8 B1 H1 108.9(7) . . ?
C12 B1 H1 108.2(7) . . ?

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 C3 C2 -0.22(14) . . . . ?
C7 N1 C3 C2 -179.52(11) . . . . ?
C1 N1 C3 C6 176.54(12) . . . . ?
C7 N1 C3 C6 -2.76(18) . . . . ?
C3 N1 C1 N2 -0.35(13) . . . . ?
C7 N1 C1 N2 178.91(11) . . . . ?
C3 N1 C1 B1 -176.87(13) . . . . ?
C7 N1 C1 B1 2.4(2) . . . . ?
C2 N2 C1 N1 0.80(13) . . . . ?
C4 N2 C1 N1 -174.79(11) . . . . ?
C2 N2 C1 B1 177.76(11) . . . . ?
C4 N2 C1 B1 2.17(19) . . . . ?
C11 C12 C13 C14 63.52(14) . . . . ?
B1 C12 C13 C14 -59.41(14) . . . . ?
C12 C13 C14 C15 50.86(15) . . . . ?
N1 C3 C2 N2 0.69(14) . . . . ?
C6 C3 C2 N2 -175.69(13) . . . . ?
N1 C3 C2 C5 -179.92(13) . . . . ?
C6 C3 C2 C5 3.7(2) . . . . ?
C1 N2 C2 C3 -0.97(14) . . . . ?
C4 N2 C2 C3 174.81(11) . . . . ?
C1 N2 C2 C5 179.58(11) . . . . ?
C4 N2 C2 C5 -4.65(18) . . . . ?
C15 C8 C9 C10 114.86(12) . . . . ?
B1 C8 C9 C10 -4.19(15) . . . . ?
C8 C9 C10 C11 -51.35(15) . . . . ?
C9 C10 C11 C12 50.19(15) . . . . ?
C13 C12 C11 C10 -113.55(12) . . . . ?
B1 C12 C11 C10 6.45(15) . . . . ?
C13 C14 C15 C8 -50.75(16) . . . . ?
C9 C8 C15 C14 -63.69(14) . . . . ?
B1 C8 C15 C14 58.89(14) . . . . ?
N1 C1 B1 C8 -4.1(2) . . . . ?
N2 C1 B1 C8 179.94(11) . . . . ?
N1 C1 B1 C12 -127.37(14) . . . . ?
N2 C1 B1 C12 56.67(16) . . . . ?
C15 C8 B1 C1 167.51(11) . . . . ?
C9 C8 B1 C1 -71.70(15) . . . . ?
C15 C8 B1 C12 -65.18(12) . . . . ?
C9 C8 B1 C12 55.62(13) . . . . ?
C13 C12 B1 C1 -162.55(11) . . . . ?
C11 C12 B1 C1 75.01(13) . . . . ?
C13 C12 B1 C8 65.73(12) . . . . ?
C11 C12 B1 C8 -56.72(13) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.034
####################################################################### 
# 
# 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_rp001_0m
_database_code_depnum_ccdc_archive 'CCDC 1035572'
_audit_update_record             
;
2014-11-23 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_formula_sum            'C13 H21 B Cl2 N2'
_chemical_formula_weight         287.03

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.8877(3)
_cell_length_b                   14.4614(5)
_cell_length_c                   10.8854(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.815(2)
_cell_angle_gamma                90.00
_cell_volume                     1398.38(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7442
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8963
_exptl_absorpt_correction_T_max  0.9158
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10673
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         27.52
_reflns_number_total             3198
_reflns_number_gt                2839
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0431P)²+1.0712P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3198
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H1 H 0.809(2) 0.4061(14) 0.4719(18) 0.024(5) Uiso 1 1 d . . .
Cl2 Cl 1.14416(5) 0.55690(3) 0.11794(4) 0.02465(12) Uani 1 1 d . . .
Cl1 Cl 1.42860(4) 0.48621(3) 0.32461(4) 0.02619(12) Uani 1 1 d . . .
N1 N 1.17689(14) 0.40463(9) 0.40864(11) 0.0167(3) Uani 1 1 d . . .
N2 N 1.00122(15) 0.44846(9) 0.28094(12) 0.0166(3) Uani 1 1 d . . .
C8 C 0.9474(2) 0.13117(12) 0.45652(17) 0.0265(4) Uani 1 1 d . . .
H8A H 1.0245 0.0847 0.4363 0.032 Uiso 1 1 calc R . .
H8B H 0.8586 0.0977 0.4866 0.032 Uiso 1 1 calc R . .
C7 C 1.01041(19) 0.19433(12) 0.55908(16) 0.0245(4) Uani 1 1 d . . .
H7A H 1.1157 0.2102 0.5406 0.029 Uiso 1 1 calc R . .
H7B H 1.0127 0.1591 0.6371 0.029 Uiso 1 1 calc R . .
C6 C 0.92270(18) 0.28517(11) 0.57869(14) 0.0193(3) Uani 1 1 d . . .
H6A H 0.9826 0.3249 0.6374 0.023 Uiso 1 1 calc R . .
C1 C 1.02693(17) 0.39632(10) 0.38382(13) 0.0155(3) Uani 1 1 d . . .
C4 C 1.2621(2) 0.36845(14) 0.51481(16) 0.0291(4) Uani 1 1 d . . .
H4A H 1.1957 0.3308 0.5648 0.044 Uiso 1 1 calc R . .
H4B H 1.3023 0.4200 0.5642 0.044 Uiso 1 1 calc R . .
H4C H 1.3453 0.3303 0.4868 0.044 Uiso 1 1 calc R . .
C3 C 1.13332(18) 0.48762(11) 0.24288(14) 0.0173(3) Uani 1 1 d . . .
C2 C 1.24284(17) 0.46038(11) 0.32218(14) 0.0175(3) Uani 1 1 d . . .
C9 C 0.9015(2) 0.18440(12) 0.34024(15) 0.0235(3) Uani 1 1 d . . .
H9A H 0.8460 0.1419 0.2838 0.028 Uiso 1 1 calc R . .
H9B H 0.9940 0.2039 0.2990 0.028 Uiso 1 1 calc R . .
C10 C 0.80336(18) 0.27036(11) 0.36020(14) 0.0183(3) Uani 1 1 d . . .
H10A H 0.7858 0.3013 0.2788 0.022 Uiso 1 1 calc R . .
C11 C 0.64899(18) 0.24964(12) 0.41418(16) 0.0235(3) Uani 1 1 d . . .
H11A H 0.5869 0.3064 0.4082 0.028 Uiso 1 1 calc R . .
H11B H 0.5983 0.2017 0.3628 0.028 Uiso 1 1 calc R . .
C12 C 0.65263(19) 0.21659(12) 0.54851(16) 0.0238(3) Uani 1 1 d . . .
H12A H 0.5511 0.2248 0.5817 0.029 Uiso 1 1 calc R . .
H12B H 0.6757 0.1496 0.5500 0.029 Uiso 1 1 calc R . .
C13 C 0.7672(2) 0.26669(12) 0.63360(15) 0.0238(4) Uani 1 1 d . . .
H13A H 0.7825 0.2294 0.7093 0.029 Uiso 1 1 calc R . .
H13B H 0.7235 0.3267 0.6579 0.029 Uiso 1 1 calc R . .
C5 C 0.85479(19) 0.46622(13) 0.22097(16) 0.0256(4) Uani 1 1 d . . .
H5A H 0.7770 0.4315 0.2630 0.038 Uiso 1 1 calc R . .
H5B H 0.8569 0.4466 0.1349 0.038 Uiso 1 1 calc R . .
H5C H 0.8323 0.5325 0.2248 0.038 Uiso 1 1 calc R . .
B1 B 0.88999(19) 0.34387(12) 0.45237(15) 0.0164(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
Cl2 C3 1.6944(15) . ?
Cl1 C2 1.6921(16) . ?
N1 C1 1.3568(19) . ?
N1 C2 1.3836(19) . ?
N1 C4 1.458(2) . ?
N2 C1 1.3633(19) . ?
N2 C3 1.379(2) . ?
N2 C5 1.460(2) . ?
C8 C9 1.526(2) . ?
C8 C7 1.535(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C7 C6 1.546(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 C13 1.546(2) . ?
C6 B1 1.634(2) . ?
C6 H6A 1.0000 . ?
C1 B1 1.634(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C3 C2 1.340(2) . ?
C9 C10 1.538(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.539(2) . ?
C10 B1 1.637(2) . ?
C10 H10A 1.0000 . ?
C11 C12 1.538(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.536(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
B1 H1 1.18(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
C1 N1 C2 110.54(13) . . ?
C1 N1 C4 127.44(13) . . ?
C2 N1 C4 121.85(13) . . ?
C1 N2 C3 110.60(13) . . ?
C1 N2 C5 126.04(13) . . ?
C3 N2 C5 123.27(13) . . ?
C9 C8 C7 112.65(14) . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C8 C7 C6 115.60(14) . . ?
C8 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
C7 C6 C13 111.55(14) . . ?
C7 C6 B1 113.72(13) . . ?
C13 C6 B1 106.12(13) . . ?
C7 C6 H6A 108.4 . . ?
C13 C6 H6A 108.4 . . ?
B1 C6 H6A 108.4 . . ?
N1 C1 N2 104.63(13) . . ?
N1 C1 B1 133.73(13) . . ?
N2 C1 B1 121.59(13) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C3 N2 107.08(13) . . ?
C2 C3 Cl2 129.23(13) . . ?
N2 C3 Cl2 123.68(12) . . ?
C3 C2 N1 107.15(13) . . ?
C3 C2 Cl1 129.33(13) . . ?
N1 C2 Cl1 123.52(12) . . ?
C8 C9 C10 115.36(13) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C9 C10 C11 114.39(14) . . ?
C9 C10 B1 110.71(13) . . ?
C11 C10 B1 107.46(13) . . ?
C9 C10 H10A 108.0 . . ?
C11 C10 H10A 108.0 . . ?
B1 C10 H10A 108.0 . . ?
C12 C11 C10 115.56(13) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 114.85(13) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 C6 115.59(13) . . ?
C12 C13 H13A 108.4 . . ?
C6 C13 H13A 108.4 . . ?
C12 C13 H13B 108.4 . . ?
C6 C13 H13B 108.4 . . ?
H13A C13 H13B 107.4 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 B1 C6 120.67(13) . . ?
C1 B1 C10 111.35(12) . . ?
C6 B1 C10 104.24(12) . . ?
C1 B1 H1 101.3(10) . . ?
C6 B1 H1 109.8(10) . . ?
C10 B1 H1 109.3(10) . . ?

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
C9 C8 C7 C6 43.6(2) . . . . ?
C8 C7 C6 C13 69.73(18) . . . . ?
C8 C7 C6 B1 -50.25(19) . . . . ?
C2 N1 C1 N2 -0.40(16) . . . . ?
C4 N1 C1 N2 174.78(16) . . . . ?
C2 N1 C1 B1 -177.78(15) . . . . ?
C4 N1 C1 B1 -2.6(3) . . . . ?
C3 N2 C1 N1 0.36(16) . . . . ?
C5 N2 C1 N1 -176.37(15) . . . . ?
C3 N2 C1 B1 178.13(13) . . . . ?
C5 N2 C1 B1 1.4(2) . . . . ?
C1 N2 C3 C2 -0.18(18) . . . . ?
C5 N2 C3 C2 176.66(15) . . . . ?
C1 N2 C3 Cl2 -179.97(11) . . . . ?
C5 N2 C3 Cl2 -3.1(2) . . . . ?
N2 C3 C2 N1 -0.07(17) . . . . ?
Cl2 C3 C2 N1 179.70(12) . . . . ?
N2 C3 C2 Cl1 -179.55(12) . . . . ?
Cl2 C3 C2 Cl1 0.2(3) . . . . ?
C1 N1 C2 C3 0.30(18) . . . . ?
C4 N1 C2 C3 -175.20(15) . . . . ?
C1 N1 C2 Cl1 179.82(11) . . . . ?
C4 N1 C2 Cl1 4.3(2) . . . . ?
C7 C8 C9 C10 -48.5(2) . . . . ?
C8 C9 C10 C11 -62.97(19) . . . . ?
C8 C9 C10 B1 58.61(18) . . . . ?
C9 C10 C11 C12 69.33(19) . . . . ?
B1 C10 C11 C12 -54.02(18) . . . . ?
C10 C11 C12 C13 40.2(2) . . . . ?
C11 C12 C13 C6 -41.7(2) . . . . ?
C7 C6 C13 C12 -67.94(18) . . . . ?
B1 C6 C13 C12 56.43(18) . . . . ?
N1 C1 B1 C6 -0.5(3) . . . . ?
N2 C1 B1 C6 -177.53(13) . . . . ?
N1 C1 B1 C10 -123.11(17) . . . . ?
N2 C1 B1 C10 59.86(18) . . . . ?
C7 C6 B1 C1 -70.72(18) . . . . ?
C13 C6 B1 C1 166.27(14) . . . . ?
C7 C6 B1 C10 55.23(17) . . . . ?
C13 C6 B1 C10 -67.77(15) . . . . ?
C9 C10 B1 C1 73.18(16) . . . . ?
C11 C10 B1 C1 -161.24(13) . . . . ?
C9 C10 B1 C6 -58.44(16) . . . . ?
C11 C10 B1 C6 67.14(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_jf056_0m
_database_code_depnum_ccdc_archive 'CCDC 1035573'
_audit_update_record             
;
2014-11-23 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_formula_sum            'C37 H20 B2 Cl2 F20 N2'
_chemical_formula_weight         965.07

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pc

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

_cell_length_a                   10.6012(7)
_cell_length_b                   10.7318(7)
_cell_length_c                   16.8601(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.327(2)
_cell_angle_gamma                90.00
_cell_volume                     1849.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    149(2)
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.50

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      149(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16149
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         27.50
_reflns_number_total             7641
_reflns_number_gt                7235
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0342P)²+0.2361P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_number_reflns         7641
_refine_ls_number_parameters     568
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0628
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.48379(19) 0.68100(19) 0.18740(13) 0.0219(4) Uani 1 1 d . . .
B2 B 0.92591(18) 0.13538(17) 0.05264(12) 0.0173(4) Uani 1 1 d . . .
C2 C 0.75156(16) 0.65696(16) 0.07915(11) 0.0197(3) Uani 1 1 d . . .
C35 C 0.90864(18) -0.15800(16) -0.14033(11) 0.0217(4) Uani 1 1 d . . .
C36 C 1.00266(17) -0.16539(16) -0.06685(11) 0.0205(4) Uani 1 1 d . . .
C19 C 0.99932(16) -0.00138(16) 0.18750(11) 0.0205(3) Uani 1 1 d . . .
C21 C 0.67681(17) 0.07684(16) 0.05535(11) 0.0219(4) Uani 1 1 d . . .
C6 C 0.36475(17) 0.77092(18) 0.17156(12) 0.0272(4) Uani 1 1 d . . .
H6A H 0.3551 0.8165 0.1186 0.033 Uiso 1 1 calc R . .
C34 C 0.82246(17) -0.05949(17) -0.15251(11) 0.0225(4) Uani 1 1 d . . .
C16 C 1.18760(18) 0.15481(19) 0.27238(12) 0.0257(4) Uani 1 1 d . . .
C20 C 0.78135(17) 0.15991(16) 0.07003(11) 0.0189(3) Uani 1 1 d . . .
C37 C 1.00777(16) -0.07685(16) -0.00665(10) 0.0186(3) Uani 1 1 d . . .
C25 C 0.76170(17) 0.26431(16) 0.11387(11) 0.0210(4) Uani 1 1 d . . .
C3 C 0.64536(17) 0.66934(17) 0.01445(11) 0.0222(4) Uani 1 1 d . . .
C32 C 0.92138(16) 0.02183(15) -0.01416(11) 0.0186(3) Uani 1 1 d . . .
C14 C 1.01980(17) 0.10590(16) 0.14616(11) 0.0192(3) Uani 1 1 d . . .
C22 C 0.56345(18) 0.09580(18) 0.07965(12) 0.0269(4) Uani 1 1 d . . .
C28 C 0.96852(19) 0.44284(17) -0.07337(11) 0.0243(4) Uani 1 1 d . . .
C31 C 1.11149(18) 0.24541(17) 0.00214(11) 0.0226(4) Uani 1 1 d . . .
C26 C 0.98310(16) 0.25213(16) 0.00822(11) 0.0192(3) Uani 1 1 d . . .
C17 C 1.16536(18) 0.04521(19) 0.30908(11) 0.0260(4) Uani 1 1 d . . .
C33 C 0.83190(17) 0.02681(16) -0.09092(11) 0.0214(4) Uani 1 1 d . . .
C4 C 0.79506(17) 0.6521(2) 0.23244(11) 0.0273(4) Uani 1 1 d . . .
H4A H 0.7429 0.6567 0.2725 0.041 Uiso 1 1 calc R . .
H4B H 0.8578 0.7211 0.2418 0.041 Uiso 1 1 calc R . .
H4C H 0.8424 0.5727 0.2389 0.041 Uiso 1 1 calc R . .
C9 C 0.50466(19) 0.68159(19) 0.34294(12) 0.0289(4) Uani 1 1 d . . .
H9A H 0.4761 0.6298 0.3836 0.035 Uiso 1 1 calc R . .
H9B H 0.5968 0.7054 0.3679 0.035 Uiso 1 1 calc R . .
C13 C 0.23675(18) 0.70023(19) 0.17029(13) 0.0292(4) Uani 1 1 d . . .
H13A H 0.1738 0.7607 0.1823 0.035 Uiso 1 1 calc R . .
H13B H 0.1989 0.6686 0.1138 0.035 Uiso 1 1 calc R . .
C24 C 0.65050(19) 0.28730(17) 0.13880(12) 0.0263(4) Uani 1 1 d . . .
C23 C 0.54951(18) 0.20148(19) 0.12217(13) 0.0293(4) Uani 1 1 d . . .
C8 C 0.4213(2) 0.8011(2) 0.32795(14) 0.0346(5) Uani 1 1 d . . .
H8A H 0.3318 0.7807 0.3314 0.042 Uiso 1 1 calc R . .
H8B H 0.4590 0.8617 0.3721 0.042 Uiso 1 1 calc R . .
C29 C 1.0973(2) 0.43298(18) -0.07487(12) 0.0282(4) Uani 1 1 d . . .
C27 C 0.91521(17) 0.35421(16) -0.03162(11) 0.0213(4) Uani 1 1 d . . .
C5 C 0.40308(19) 0.6911(2) -0.00683(13) 0.0378(5) Uani 1 1 d . . .
H5A H 0.3428 0.6977 0.0282 0.057 Uiso 1 1 calc R . .
H5B H 0.3811 0.6172 -0.0419 0.057 Uiso 1 1 calc R . .
H5C H 0.3954 0.7657 -0.0413 0.057 Uiso 1 1 calc R . .
C10 C 0.49947(17) 0.60050(17) 0.26608(11) 0.0230(4) Uani 1 1 d . . .
H10A H 0.5799 0.5479 0.2755 0.028 Uiso 1 1 calc R . .
C1 C 0.57651(17) 0.67408(16) 0.12820(12) 0.0203(3) Uani 1 1 d . . .
C18 C 1.06921(18) -0.03334(17) 0.26597(11) 0.0234(4) Uani 1 1 d . . .
C15 C 1.11524(18) 0.18287(17) 0.19347(11) 0.0229(4) Uani 1 1 d . . .
C11 C 0.37532(19) 0.51735(19) 0.24025(14) 0.0323(4) Uani 1 1 d . . .
H11A H 0.3736 0.4753 0.1877 0.039 Uiso 1 1 calc R . .
H11B H 0.3801 0.4521 0.2824 0.039 Uiso 1 1 calc R . .
C12 C 0.24896(19) 0.5911(2) 0.22991(14) 0.0317(4) Uani 1 1 d . . .
H12A H 0.2451 0.6233 0.2843 0.038 Uiso 1 1 calc R . .
H12B H 0.1736 0.5344 0.2097 0.038 Uiso 1 1 calc R . .
C7 C 0.4127(2) 0.86161(18) 0.24551(14) 0.0338(5) Uani 1 1 d . . .
H7A H 0.5001 0.8940 0.2453 0.041 Uiso 1 1 calc R . .
H7B H 0.3520 0.9334 0.2384 0.041 Uiso 1 1 calc R . .
C30 C 1.16973(19) 0.33378(18) -0.03571(13) 0.0270(4) Uani 1 1 d . . .
Cl1 Cl 0.91007(4) 0.64136(4) 0.08041(3) 0.02611(9) Uani 1 1 d . . .
Cl2 Cl 0.63517(5) 0.67377(5) -0.08715(3) 0.03623(12) Uani 1 1 d . . .
F1 F 1.14348(11) 0.29396(10) 0.16531(7) 0.0298(2) Uani 1 1 d . . .
F2 F 1.28031(12) 0.23369(12) 0.31368(7) 0.0393(3) Uani 1 1 d . . .
F3 F 1.23451(12) 0.01791(12) 0.38607(7) 0.0360(3) Uani 1 1 d . . .
F4 F 1.04412(12) -0.14054(10) 0.30133(7) 0.0324(3) Uani 1 1 d . . .
F5 F 0.90486(10) -0.08344(10) 0.14952(6) 0.0261(2) Uani 1 1 d . . .
F6 F 0.68051(11) -0.03277(10) 0.01582(7) 0.0307(2) Uani 1 1 d . . .
F7 F 0.46801(11) 0.00902(12) 0.06322(8) 0.0401(3) Uani 1 1 d . . .
F8 F 0.44294(12) 0.22130(13) 0.14837(9) 0.0467(3) Uani 1 1 d . . .
F9 F 0.63965(12) 0.39109(11) 0.18147(9) 0.0402(3) Uani 1 1 d . . .
F10 F 0.85726(10) 0.35139(10) 0.13552(7) 0.0261(2) Uani 1 1 d . . .
F11 F 0.78869(10) 0.37399(10) -0.03355(7) 0.0269(2) Uani 1 1 d . . .
F12 F 0.89443(12) 0.53765(10) -0.11248(7) 0.0325(3) Uani 1 1 d . . .
F13 F 1.15142(13) 0.51835(11) -0.11414(8) 0.0409(3) Uani 1 1 d . . .
F14 F 1.29709(12) 0.32384(12) -0.03511(9) 0.0413(3) Uani 1 1 d . . .
F15 F 1.18771(10) 0.14827(10) 0.03653(7) 0.0287(2) Uani 1 1 d . . .
F16 F 0.74454(11) 0.12204(10) -0.10824(7) 0.0299(2) Uani 1 1 d . . .
F17 F 0.73108(12) -0.04821(12) -0.22510(7) 0.0359(3) Uani 1 1 d . . .
F18 F 0.90271(11) -0.24196(10) -0.20006(6) 0.0296(2) Uani 1 1 d . . .
F19 F 1.09205(11) -0.25803(10) -0.05398(7) 0.0295(2) Uani 1 1 d . . .
F20 F 1.10581(10) -0.09185(10) 0.06241(6) 0.0255(2) Uani 1 1 d . . .
N1 N 0.53819(14) 0.68024(14) 0.04517(9) 0.0223(3) Uani 1 1 d . . .
N2 N 0.70814(14) 0.66064(13) 0.14874(9) 0.0189(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
B1 C6 1.555(3) . ?
B1 C10 1.555(3) . ?
B1 C1 1.577(3) . ?
B2 C32 1.651(2) . ?
B2 C26 1.655(2) . ?
B2 C20 1.656(2) . ?
B2 C14 1.658(3) . ?
C2 C3 1.351(3) . ?
C2 N2 1.370(2) . ?
C2 Cl1 1.6832(17) . ?
C35 F18 1.3404(19) . ?
C35 C36 1.372(3) . ?
C35 C34 1.377(3) . ?
C36 F19 1.351(2) . ?
C36 C37 1.381(2) . ?
C19 F5 1.360(2) . ?
C19 C18 1.378(3) . ?
C19 C14 1.392(2) . ?
C21 F6 1.358(2) . ?
C21 C22 1.383(3) . ?
C21 C20 1.393(2) . ?
C6 C13 1.550(3) . ?
C6 C7 1.557(3) . ?
C34 F17 1.351(2) . ?
C34 C33 1.375(3) . ?
C16 F2 1.344(2) . ?
C16 C17 1.378(3) . ?
C16 C15 1.382(3) . ?
C20 C25 1.388(2) . ?
C37 F20 1.350(2) . ?
C37 C32 1.384(2) . ?
C25 F10 1.355(2) . ?
C25 C24 1.374(3) . ?
C3 N1 1.373(2) . ?
C3 Cl2 1.6883(18) . ?
C32 C33 1.389(3) . ?
C14 C15 1.384(3) . ?
C22 F7 1.349(2) . ?
C22 C23 1.371(3) . ?
C28 F12 1.347(2) . ?
C28 C29 1.377(3) . ?
C28 C27 1.389(3) . ?
C31 F15 1.352(2) . ?
C31 C30 1.377(3) . ?
C31 C26 1.394(2) . ?
C26 C27 1.383(3) . ?
C17 F3 1.344(2) . ?
C17 C18 1.373(3) . ?
C33 F16 1.358(2) . ?
C4 N2 1.470(2) . ?
C9 C8 1.541(3) . ?
C9 C10 1.550(3) . ?
C13 C12 1.527(3) . ?
C24 F9 1.347(2) . ?
C24 C23 1.384(3) . ?
C23 F8 1.334(2) . ?
C8 C7 1.515(3) . ?
C29 F13 1.344(2) . ?
C29 C30 1.375(3) . ?
C27 F11 1.350(2) . ?
C5 N1 1.473(2) . ?
C10 C11 1.554(3) . ?
C1 N1 1.352(2) . ?
C1 N2 1.354(2) . ?
C18 F4 1.354(2) . ?
C15 F1 1.346(2) . ?
C11 C12 1.526(3) . ?
C30 F14 1.352(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 B1 C10 112.97(15) . . ?
C6 B1 C1 122.28(16) . . ?
C10 B1 C1 124.75(16) . . ?
C32 B2 C26 101.43(13) . . ?
C32 B2 C20 112.13(14) . . ?
C26 B2 C20 115.26(14) . . ?
C32 B2 C14 114.19(14) . . ?
C26 B2 C14 112.05(14) . . ?
C20 B2 C14 102.30(13) . . ?
C3 C2 N2 106.96(14) . . ?
C3 C2 Cl1 129.49(14) . . ?
N2 C2 Cl1 123.54(14) . . ?
F18 C35 C36 121.22(16) . . ?
F18 C35 C34 120.44(16) . . ?
C36 C35 C34 118.31(16) . . ?
F19 C36 C35 119.93(15) . . ?
F19 C36 C37 119.92(16) . . ?
C35 C36 C37 120.13(16) . . ?
F5 C19 C18 115.66(16) . . ?
F5 C19 C14 119.51(15) . . ?
C18 C19 C14 124.82(16) . . ?
F6 C21 C22 114.39(15) . . ?
F6 C21 C20 121.13(15) . . ?
C22 C21 C20 124.48(17) . . ?
C13 C6 B1 111.50(16) . . ?
C13 C6 C7 114.60(16) . . ?
B1 C6 C7 99.91(15) . . ?
F17 C34 C33 121.03(16) . . ?
F17 C34 C35 119.52(16) . . ?
C33 C34 C35 119.44(16) . . ?
F2 C16 C17 119.57(17) . . ?
F2 C16 C15 120.36(18) . . ?
C17 C16 C15 120.07(17) . . ?
C25 C20 C21 112.77(16) . . ?
C25 C20 B2 119.92(15) . . ?
C21 C20 B2 126.67(15) . . ?
F20 C37 C36 115.07(15) . . ?
F20 C37 C32 120.68(15) . . ?
C36 C37 C32 124.26(16) . . ?
F10 C25 C24 115.74(15) . . ?
F10 C25 C20 119.56(15) . . ?
C24 C25 C20 124.70(17) . . ?
C2 C3 N1 107.45(15) . . ?
C2 C3 Cl2 129.65(14) . . ?
N1 C3 Cl2 122.90(14) . . ?
C37 C32 C33 112.78(15) . . ?
C37 C32 B2 127.09(16) . . ?
C33 C32 B2 119.78(15) . . ?
C15 C14 C19 113.08(16) . . ?
C15 C14 B2 126.72(16) . . ?
C19 C14 B2 120.01(15) . . ?
F7 C22 C23 120.00(17) . . ?
F7 C22 C21 120.05(17) . . ?
C23 C22 C21 119.93(17) . . ?
F12 C28 C29 120.15(17) . . ?
F12 C28 C27 120.18(17) . . ?
C29 C28 C27 119.67(17) . . ?
F15 C31 C30 116.06(16) . . ?
F15 C31 C26 119.54(15) . . ?
C30 C31 C26 124.39(17) . . ?
C27 C26 C31 113.46(16) . . ?
C27 C26 B2 127.85(15) . . ?
C31 C26 B2 118.42(15) . . ?
F3 C17 C18 121.10(18) . . ?
F3 C17 C16 120.37(17) . . ?
C18 C17 C16 118.51(17) . . ?
F16 C33 C34 115.79(16) . . ?
F16 C33 C32 119.23(15) . . ?
C34 C33 C32 124.97(16) . . ?
C8 C9 C10 116.01(17) . . ?
C12 C13 C6 116.42(16) . . ?
F9 C24 C25 120.86(17) . . ?
F9 C24 C23 119.19(16) . . ?
C25 C24 C23 119.93(17) . . ?
F8 C23 C22 121.53(18) . . ?
F8 C23 C24 120.29(18) . . ?
C22 C23 C24 118.17(17) . . ?
C7 C8 C9 113.57(17) . . ?
F13 C29 C30 120.51(18) . . ?
F13 C29 C28 120.72(19) . . ?
C30 C29 C28 118.76(17) . . ?
F11 C27 C26 121.49(15) . . ?
F11 C27 C28 114.50(15) . . ?
C26 C27 C28 124.00(17) . . ?
C9 C10 C11 113.39(15) . . ?
C9 C10 B1 111.94(16) . . ?
C11 C10 B1 100.85(15) . . ?
N1 C1 N2 106.10(15) . . ?
N1 C1 B1 125.88(15) . . ?
N2 C1 B1 128.02(16) . . ?
F4 C18 C17 119.55(17) . . ?
F4 C18 C19 121.05(16) . . ?
C17 C18 C19 119.40(17) . . ?
F1 C15 C16 114.46(16) . . ?
F1 C15 C14 121.48(16) . . ?
C16 C15 C14 124.05(18) . . ?
C12 C11 C10 112.78(16) . . ?
C11 C12 C13 113.09(17) . . ?
C8 C7 C6 113.24(17) . . ?
F14 C30 C29 119.62(17) . . ?
F14 C30 C31 120.77(18) . . ?
C29 C30 C31 119.61(17) . . ?
C1 N1 C3 109.54(14) . . ?
C1 N1 C5 126.79(15) . . ?
C3 N1 C5 123.62(16) . . ?
C1 N2 C2 109.94(15) . . ?
C1 N2 C4 126.48(15) . . ?
C2 N2 C4 123.58(14) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.154
_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_jf053_0m
_database_code_depnum_ccdc_archive 'CCDC 1035574'
_audit_update_record             
;
2014-11-23 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_formula_sum            'C11 H24 B P'
_chemical_formula_weight         198.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   11.0408(11)
_cell_length_b                   6.6868(6)
_cell_length_c                   16.9825(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.038(5)
_cell_angle_gamma                90.00
_cell_volume                     1244.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4157
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.42

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.057
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9481
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9241
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2187
_reflns_number_gt                1785
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0373P)²+0.3394P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2187
_refine_ls_number_parameters     125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.30414(4) 1.02667(7) 0.80027(2) 0.01700(14) Uani 1 1 d . . .
C3 C 0.25749(17) 0.9124(3) 0.51183(10) 0.0257(4) Uani 1 1 d . . .
H3A H 0.1706 0.8818 0.4945 0.031 Uiso 1 1 calc R . .
H3B H 0.3011 0.9086 0.4643 0.031 Uiso 1 1 calc R . .
C4 C 0.26657(17) 1.1254(3) 0.54649(10) 0.0235(4) Uani 1 1 d . . .
H4A H 0.2136 1.2146 0.5107 0.028 Uiso 1 1 calc R . .
H4B H 0.3516 1.1728 0.5470 0.028 Uiso 1 1 calc R . .
C5 C 0.23033(15) 1.1454(2) 0.63111(10) 0.0197(4) Uani 1 1 d . . .
H5 H 0.2523 1.2830 0.6511 0.024 Uiso 1 1 calc R . .
C10 C 0.32421(18) 1.2889(3) 0.82471(11) 0.0282(5) Uani 1 1 d . . .
H10A H 0.3307 1.3059 0.8824 0.042 Uiso 1 1 calc R . .
H10B H 0.2540 1.3648 0.7995 0.042 Uiso 1 1 calc R . .
H10C H 0.3988 1.3381 0.8054 0.042 Uiso 1 1 calc R . .
C9 C 0.17191(15) 0.9516(3) 0.84723(10) 0.0253(4) Uani 1 1 d . . .
H9A H 0.1645 0.8056 0.8458 0.038 Uiso 1 1 calc R . .
H9B H 0.0982 1.0115 0.8187 0.038 Uiso 1 1 calc R . .
H9C H 0.1817 0.9973 0.9025 0.038 Uiso 1 1 calc R . .
C11 C 0.42933(16) 0.8999(3) 0.85850(10) 0.0252(4) Uani 1 1 d . . .
H11A H 0.5069 0.9501 0.8438 0.038 Uiso 1 1 calc R . .
H11B H 0.4234 0.7558 0.8482 0.038 Uiso 1 1 calc R . .
H11C H 0.4255 0.9251 0.9150 0.038 Uiso 1 1 calc R . .
C6 C 0.09299(16) 1.1127(3) 0.63493(11) 0.0249(4) Uani 1 1 d . . .
H6A H 0.0466 1.2030 0.5960 0.030 Uiso 1 1 calc R . .
H6B H 0.0743 1.1520 0.6883 0.030 Uiso 1 1 calc R . .
C7 C 0.04745(16) 0.8971(3) 0.61824(11) 0.0286(4) Uani 1 1 d . . .
H7A H 0.0339 0.8774 0.5601 0.034 Uiso 1 1 calc R . .
H7B H -0.0325 0.8823 0.6384 0.034 Uiso 1 1 calc R . .
C8 C 0.13272(16) 0.7297(3) 0.65476(11) 0.0247(4) Uani 1 1 d . . .
H8A H 0.1102 0.6039 0.6258 0.030 Uiso 1 1 calc R . .
H8B H 0.1174 0.7099 0.7105 0.030 Uiso 1 1 calc R . .
C1 C 0.27096(15) 0.7652(2) 0.65391(9) 0.0181(4) Uani 1 1 d . . .
H1 H 0.3170 0.6631 0.6887 0.022 Uiso 1 1 calc R . .
C2 C 0.31008(17) 0.7492(3) 0.56972(10) 0.0230(4) Uani 1 1 d . . .
H2A H 0.4003 0.7550 0.5741 0.028 Uiso 1 1 calc R . .
H2B H 0.2844 0.6171 0.5472 0.028 Uiso 1 1 calc R . .
B1 B 0.31131(17) 0.9855(3) 0.68666(11) 0.0162(4) Uani 1 1 d . . .
H12 H 0.4139(15) 1.018(3) 0.6891(10) 0.025(5) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C11 1.8089(17) . ?
P1 C10 1.8093(18) . ?
P1 C9 1.8179(17) . ?
P1 B1 1.9601(19) . ?
C3 C2 1.534(2) . ?
C3 C4 1.539(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.544(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.541(2) . ?
C5 B1 1.621(2) . ?
C5 H5 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C6 C7 1.541(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.543(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C1 1.546(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C1 C2 1.547(2) . ?
C1 B1 1.618(3) . ?
C1 H1 1.0000 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
B1 H12 1.149(17) . ?

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
C11 P1 C10 105.36(9) . . ?
C11 P1 C9 103.40(8) . . ?
C10 P1 C9 104.44(9) . . ?
C11 P1 B1 110.61(8) . . ?
C10 P1 B1 110.08(8) . . ?
C9 P1 B1 121.63(8) . . ?
C2 C3 C4 114.27(14) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C5 115.10(14) . . ?
C3 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
C5 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
C6 C5 C4 113.28(14) . . ?
C6 C5 B1 110.93(14) . . ?
C4 C5 B1 107.27(13) . . ?
C6 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
B1 C5 H5 108.4 . . ?
P1 C10 H10A 109.5 . . ?
P1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
P1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
P1 C9 H9A 109.5 . . ?
P1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
P1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
P1 C11 H11A 109.5 . . ?
P1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
P1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C6 C7 115.18(14) . . ?
C5 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C6 C7 C8 115.81(14) . . ?
C6 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
C8 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C7 C8 C1 116.05(14) . . ?
C7 C8 H8A 108.3 . . ?
C1 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
C1 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C8 C1 C2 112.68(14) . . ?
C8 C1 B1 111.54(14) . . ?
C2 C1 B1 106.52(13) . . ?
C8 C1 H1 108.7 . . ?
C2 C1 H1 108.7 . . ?
B1 C1 H1 108.7 . . ?
C3 C2 C1 114.61(14) . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C1 B1 C5 106.96(13) . . ?
C1 B1 P1 115.07(12) . . ?
C5 B1 P1 113.22(12) . . ?
C1 B1 H12 114.3(9) . . ?
C5 B1 H12 111.6(9) . . ?
P1 B1 H12 95.5(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
C2 C3 C4 C5 -44.6(2) . . . . ?
C3 C4 C5 C6 -68.77(19) . . . . ?
C3 C4 C5 B1 53.99(19) . . . . ?
C4 C5 C6 C7 68.50(19) . . . . ?
B1 C5 C6 C7 -52.21(19) . . . . ?
C5 C6 C7 C8 40.4(2) . . . . ?
C6 C7 C8 C1 -38.5(2) . . . . ?
C7 C8 C1 C2 -71.36(19) . . . . ?
C7 C8 C1 B1 48.4(2) . . . . ?
C4 C3 C2 C1 46.0(2) . . . . ?
C8 C1 C2 C3 65.95(19) . . . . ?
B1 C1 C2 C3 -56.66(18) . . . . ?
C8 C1 B1 C5 -57.72(17) . . . . ?
C2 C1 B1 C5 65.60(16) . . . . ?
C8 C1 B1 P1 68.99(16) . . . . ?
C2 C1 B1 P1 -167.68(11) . . . . ?
C6 C5 B1 C1 59.75(17) . . . . ?
C4 C5 B1 C1 -64.45(17) . . . . ?
C6 C5 B1 P1 -68.05(16) . . . . ?
C4 C5 B1 P1 167.75(11) . . . . ?
C11 P1 B1 C1 74.39(14) . . . . ?
C10 P1 B1 C1 -169.58(12) . . . . ?
C9 P1 B1 C1 -47.10(16) . . . . ?
C11 P1 B1 C5 -162.16(12) . . . . ?
C10 P1 B1 C5 -46.13(14) . . . . ?
C9 P1 B1 C5 76.35(15) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043
