# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1435441'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 B N'
_chemical_formula_sum            'C19 H16 B N'
_chemical_formula_weight         269.14

_twin_information                
;
 * * * CRYSALIS TWIN DATA REDUCTION FINALIZING (Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)) * * *
Laue class: 1bar - Friedel mate is equivalent
Lattice type: P-lattice 
DC PROFFITRRPTWIN INFO: Step 1 - Loading orientation matrices (UB) of 2 components
 
DC PROFFITRRPTWIN INFO: Loading UB component 1
 
DC PROFFITRRPTWIN INFO: Loading UB component 2
 
DC PROFFITRRPTWIN INFO: Step 2 - Computing crossed twin laws
 
Twin law determination (relative to component 1)
Matrix 1 is taken from component 1 (   5.920    7.495   31.311    94.30    91.14    90.11)
Matrix 2 is taken from component 2 (   5.915    7.489   31.311    93.98    90.97    89.90)
Twin analysis: Component 1 with component 2
TL  =UB[1]-1*UB[2]:  -1.0007  -0.0002  -0.0001    -0.0003   1.0007  -0.0001     0.0184  -0.6046  -0.9995   det 1.001002
TL-1=UB[2]*UB[1]-1:  -0.9993  -0.0002   0.0001    -0.0003   0.9992  -0.0001    -0.0183  -0.6045  -1.0004   det 0.998999
Rot= -179.8008 deg around the following vectors: 
Reciprocal space (hkl): -0.0015 0.9573 -0.2892
Direct space (uvw)    : -0.0001 1.0000 0.0006
 
DC PROFFITRRPTWIN INFO: Step 3 - Loading reflections of 2 components
 
DC PROFFITRRPTWIN ALL INFO: Component 1
DC PROFFITRRPTWIN INFO: Face list of component 1 
  1:   0.0035  -0.0009  19.9929  d=   0.0172
  2:   2.9997  -3.0006   5.7474  d=   0.0984
  3:  -1.0029   4.0005 -14.3809  d=   0.0794
  4:   2.9949   1.9999 -13.2507  d=   0.0886
  5:   0.0034  -3.0004  14.7976  d=   0.0833
  6:  -0.0035   0.0009 -19.9929  d=   0.0010
  7:   1.0007   2.9989  13.1746  d=   0.0987
  8:  -3.9975   2.0006   0.8690  d=   0.1149
  9:  -1.9953  -2.0001  15.2321  d=   0.0914
 10:   1.0010  -4.9986  -1.9999  d=   0.1063
 11:  -1.0008  -1.9966 -16.7848  d=   0.0513
DC PROFFITRRPTWIN ALL INFO: Component 2
DC PROFFITRRPTWIN INFO: Face list of component 2 
  1:  -0.0024  -0.0025 -20.0010  d=   0.0172
  2:  -2.9967  -2.9995  -3.9909  d=   0.0984
  3:   1.0006   3.9988  11.9873  d=   0.0794
  4:  -2.9939   1.9986  11.9928  d=   0.0886
  5:  -0.0020  -2.9993 -12.9905  d=   0.0833
  6:   0.0024   0.0025  20.0010  d=   0.0010
  7:  -0.9999   2.9953 -15.0113  d=   0.0987
  8:   3.9943   2.0000  -2.0056  d=   0.1149
  9:   1.9951  -1.9993 -13.9933  d=   0.0914
 10:  -0.9994  -4.9948   5.0039  d=   0.1063
 11:   0.9996  -1.9934  18.0172  d=   0.0513
 
DC PROFFITRRPTWIN INFO: Step 4 - Analysing composite reflections of 2 components
 
Component 1: 18001 observations read
Component 2: 17996 observations read

21109 composite observations collected (6261 fully isolated, 14848 overlapped), 29 skipped due to one or more missing parts and 4 skipped due to I/sig<-3.0


OVERLAP STATISTICS

2 COMPONENTS

COMPONENTS 1, 2
 Overlap factor | # in range | % of all obs 
 -------------- | ---------- | ------------ 
   0.00 - 0.20  |       3421 |    16.2 <--- ALMOST SEPARATED
   0.20 - 0.40  |       2910 |    13.8
   0.40 - 0.60  |       3023 |    14.3
   0.60 - 0.80  |       3323 |    15.7
   0.80 - 1.00  |       2171 |    10.3 <--- FULLY OVERLAPPED
 -------------- | ---------- | ------------ 
      Total     |      14848 |    70.3

 
DC PROFFITRRPTWIN INFO: Step 5 - Scaling data & analysing twin ratios of 2 components
 
Computed twin ratios:
Twin 1: 72.75% (9206 common observations, 2384 merged)
Twin 2: 27.25% (7326 common observations, 2384 merged)

Preparing data for SCALE3 ABSPACK...

SCALING COMPONENT 1

10161 of 17976 reflections used for ABSPACK refinement
PROFFIT INFO: Inet (after scale3 abspack): min=-762287.1875 max=10095266.0000
PROFFIT INFO: sig(Inet) (after scale3 abspack): min=107.3130 max=61827.7813
PROFFIT INFO: 93 observations on 'bad frames' rejected


SCALING COMPONENT 2

9382 of 17981 reflections used for ABSPACK refinement
PROFFIT INFO: Inet (after scale3 abspack): min=-2648298.2500 max=10095266.0000
PROFFIT INFO: sig(Inet) (after scale3 abspack): min=101.4021 max=61827.7813
PROFFIT INFO: 125 observations on 'bad frames' rejected

Computed twin ratios:
Twin 1: 72.83% (9172 common observations, 2383 merged)
Twin 2: 27.17% (7311 common observations, 2383 merged)

DC PROFFITRRPTWIN INFO: Determining HKLF4 overlap threshold for completeness requirement (>=80.0%)
DC PROFFITRRPTWIN INFO: New HKLF4 overlap threshold - 0.53

DC PROFFITRRPTWIN INFO: Step 6 - Decomposed intensities statistics (HKLF4)
 
COMPONENT 1

 
Note: The Rint, Rsigma and RsigmaB values are computed for redundant data only!
	Mean F2 and F2/sig(F2) are given for all measured values!
Note: The RsigmaA values are computed for all measured values!

Help: For more information about computations of rint and rsigma please look into Crysalis help: 
 file:__#HELP_DTheoryAlgorithm_DataReductionOutput.html
 

Statistics vs intensity - point group symmetry: P-1
                      #        #        #      average    mean      mean        
         intensity measured   kept    unique  redundancy   F2     F2/sig(F2)   Rint   Rsigma
#--------------------------------------------------------------------------------------------
  9581023-   96768     1695     1695      398    4.3    467174.98   101.41    0.078    0.099
    95828-   38553     1347     1347      398    3.4     60527.07    35.65    0.118    0.129
    38459-   19319     1400     1400      398    3.5     27786.21    20.41    0.128    0.155
    19295-   10838     1174     1174      398    2.9     14388.64    12.34    0.139    0.154
    10815-    6204     1153     1153      398    2.9      8393.15     7.87    0.165    0.178
     6189-    3623     1164     1164      398    2.9      4770.39     4.72    0.233    0.272
     3619-    2037     1081     1081      398    2.7      2780.91     2.81    0.284    0.320
     2035-    1024     1050     1050      398    2.6      1498.57     1.57    0.414    0.456
     1024-     295     1119     1119      398    2.8       645.36     0.71    0.648    0.841
      291-   -6088      956      956      400    2.4      -119.94    -0.09    0.971    2.121
#------------------------------------------------------------------------------------------
  9581023-   -6088    12139    12139     3982    3.0     78227.34    23.31    0.088    0.112
 

Statistics vs resolution - point group symmetry: P-1
resolu-      #        #        #               average    mean      mean          
tion(A)   measured   kept    unique           redundancy   F2     F2/sig(F2)   Rint   Rsigma   RsigmaA
#------------------------------------------------------------------------------------------------------
 inf-1.85     2871     2871      398             7.2    211828.54    51.13    0.083    0.115     0.010
1.85-1.48     2273     2273      398             5.7     61769.57    20.57    0.081    0.094     0.028
1.48-1.31     1720     1720      398             4.3     26949.04     9.59    0.139    0.167     0.061
1.30-1.17     1211     1211      398             3.0     48005.57    14.89    0.110    0.119     0.038
1.17-1.07      766      766      398             1.9     54441.11    22.97    0.075    0.080     0.028
1.07-1.00      683      683      398             1.7     24247.11    13.73    0.092    0.094     0.053
1.00-0.95      720      720      398             1.8     17742.49    10.74    0.119    0.131     0.066
0.95-0.91      664      664      398             1.7     16810.94    11.77    0.108    0.107     0.064
0.91-0.87      629      629      398             1.6     13026.45     9.86    0.110    0.111     0.073
0.87-0.84      602      602      400             1.5     10231.31    10.22    0.117    0.118     0.078
#------------------------------------------------------------------------------------------------------
 inf-0.84    12139    12139     3982             3.0     78227.34    23.31    0.088    0.112     0.020
 

Statistics vs resolution (taking redundancy into account) - point group symmetry: P-1
resolu-      #        #        #       %       average    mean      mean          
tion(A)    kept     theory   unique complete  redundancy   F2     F2/sig(F2)   Rint  RsigmaB
#--------------------------------------------------------------------------------------------
 inf-1.85     2871      455      398   87.5      7.2    211828.54   140.15    0.083    0.004
1.85-1.48     2273      423      398   94.1      5.7     61769.57    51.45    0.081    0.012
1.48-1.31     1720      441      398   90.2      4.3     26949.04    21.40    0.139    0.033
1.30-1.17     1211      490      398   81.2      3.0     48005.57    28.94    0.110    0.021
1.17-1.07      766      525      398   75.8      1.9     54441.11    36.00    0.075    0.019
1.07-1.00      683      528      398   75.4      1.7     24247.11    19.10    0.092    0.035
1.00-0.95      720      496      398   80.2      1.8     17742.49    15.69    0.119    0.049
0.95-0.91      664      555      398   71.7      1.7     16810.94    15.49    0.108    0.049
0.91-0.87      629      530      398   75.1      1.6     13026.45    12.87    0.110    0.055
0.87-0.84      602      521      400   76.8      1.5     10231.31    13.13    0.117    0.058
#--------------------------------------------------------------------------------------------
 inf-0.84    12139     4964     3982   80.2      3.0     78227.34    55.14    0.088    0.013
DC PROFFITRRPTWIN INFO: Step 7 - Generating output files
 
HKLF 4
Reflections read=17882, from those 12139 with overlapping factor < 0.526 written to file C:\Users\msiegle2\Desktop\xs0463a_2\xs0463a_max2_twin1_hklf4.hkl, 5743 skipped
Use the HKLF 4 file(s) for structure solution.

HKLF 5 merged
RINT ANALYSIS FOR ALL HKLF5 REFLECTIONS
 Components measured    kept     unique redundancy F2/sig(F2) Rint      Rsigma
#------------------------------------------------------------------------------
1,2          17882     15319      5853     2.62     21.79     0.032     0.033

RINT ANALYSIS FOR OVERLAPPED REFLECTIONS
 Components measured    kept     unique redundancy F2/sig(F2) Rint      Rsigma
#------------------------------------------------------------------------------
1,2          14702     12588      4610     2.73     21.19     0.034     0.034

RINT ANALYSIS FOR ISOLATED REFLECTIONS
 Component measured     kept     unique redundancy F2/sig(F2) Rint      Rsigma
#------------------------------------------------------------------------------
     1        3180      2731      1243     2.20     24.57     0.023     0.027
     2           0         0         0     0.00      0.00     0.000     0.000

5853 merged reflections saved into file: C:\Users\msiegle2\Desktop\xs0463a_2\xs0463a_max2_twin1_hklf5.hkl

Use this hkl file in SHELXL with BASF instruction, which has (components minus 1) entries, and HKLF 5 instruction.
E.g. Two component twin: 'BASF n2' in .ins file, BASF n1 can be computed as n1 = 1.0 - n2.
E.g. Three component twin: 'BASF n2 n3' in .ins file, BASF n1 can be computed as n1 = 1.0 - (n2 + n3).

BASF 0.27173 
;

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.9219(3)
_cell_length_b                   7.4968(3)
_cell_length_c                   31.3180(19)
_cell_angle_alpha                94.271(4)
_cell_angle_beta                 91.188(4)
_cell_angle_gamma                90.053(3)
_cell_volume                     1386.21(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    5546
_cell_measurement_theta_min      4.22
_cell_measurement_theta_max      67.20

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.558
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            15319
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         4.248
_diffrn_reflns_theta_max         67.250
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5846
_reflns_number_gt                4038
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'

_refine_special_details          Twin
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1458P)²+0.4587P]
 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_number_reflns         5846
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2466
_refine_ls_wR_factor_gt          0.2349
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.9673(6) 1.1192(4) 0.29106(11) 0.0186(7) Uani 1 1 d . . . . .
C2A C 1.1094(6) 1.1745(4) 0.32563(11) 0.0183(7) Uani 1 1 d . . . . .
H2A H 1.2513 1.2268 0.3203 0.022 Uiso 1 1 calc R U . . .
C3A C 1.0485(6) 1.1549(5) 0.36776(11) 0.0205(8) Uani 1 1 d . . . . .
C4A C 1.1943(6) 1.2071(5) 0.40321(12) 0.0233(8) Uani 1 1 d . . . . .
H4A H 1.3383 1.2568 0.3984 0.028 Uiso 1 1 calc R U . . .
C5A C 1.1283(6) 1.1860(5) 0.44427(12) 0.0272(9) Uani 1 1 d . . . . .
H5A H 1.2262 1.2236 0.4676 0.033 Uiso 1 1 calc R U . . .
C6A C 0.9175(6) 1.1095(5) 0.45227(12) 0.0260(9) Uani 1 1 d . . . . .
H6A H 0.8744 1.0951 0.4809 0.031 Uiso 1 1 calc R U . . .
C7A C 0.7747(6) 1.0557(5) 0.41884(12) 0.0246(8) Uani 1 1 d . . . . .
H7A H 0.6330 1.0040 0.4245 0.030 Uiso 1 1 calc R U . . .
C8A C 0.8341(6) 1.0757(5) 0.37619(12) 0.0208(8) Uani 1 1 d . . . . .
C9A C 0.6915(6) 1.0251(5) 0.34133(11) 0.0200(8) Uani 1 1 d . . . . .
H9A H 0.5473 0.9767 0.3466 0.024 Uiso 1 1 calc R U . . .
C10A C 0.7513(6) 1.0426(5) 0.29942(11) 0.0185(7) Uani 1 1 d . . . . .
C11A C 0.6059(6) 0.9843(4) 0.26346(12) 0.0194(8) Uani 1 1 d . . . . .
H11A H 0.4592 0.9420 0.2692 0.023 Uiso 1 1 calc R U . . .
C12A C 0.6657(6) 0.9866(5) 0.22265(11) 0.0201(8) Uani 1 1 d . . . . .
H12A H 0.5648 0.9445 0.2001 0.024 Uiso 1 1 calc R U . . .
C13A C 1.0010(6) 1.0544(5) 0.16695(12) 0.0207(8) Uani 1 1 d . . . . .
C14A C 1.2084(6) 1.1354(5) 0.15845(12) 0.0220(8) Uani 1 1 d . . . . .
H14A H 1.2907 1.1969 0.1814 0.026 Uiso 1 1 calc R U . . .
C15A C 1.2964(6) 1.1282(5) 0.11754(12) 0.0238(8) Uani 1 1 d . . . . .
H15A H 1.4369 1.1846 0.1132 0.029 Uiso 1 1 calc R U . . .
C16A C 1.1825(7) 1.0401(5) 0.08303(12) 0.0266(9) Uani 1 1 d . . . . .
C17A C 0.9766(7) 0.9576(5) 0.09082(12) 0.0258(8) Uani 1 1 d . . . . .
H17A H 0.8956 0.8957 0.0678 0.031 Uiso 1 1 calc R U . . .
C18A C 0.8890(6) 0.9649(5) 0.13168(12) 0.0246(8) Uani 1 1 d . . . . .
H18A H 0.7489 0.9076 0.1359 0.030 Uiso 1 1 calc R U . . .
C19A C 1.2778(7) 1.0349(6) 0.03919(13) 0.0354(10) Uani 1 1 d . . . . .
H19A H 1.2605 1.1524 0.0278 0.053 Uiso 1 1 calc R U . . .
H19B H 1.1970 0.9447 0.0204 0.053 Uiso 1 1 calc R U . . .
H19C H 1.4384 1.0040 0.0406 0.053 Uiso 1 1 calc R U . . .
B1A B 0.9024(7) 1.0590(5) 0.21259(13) 0.0205(9) Uani 1 1 d . . . . .
N1A N 1.0292(5) 1.1300(4) 0.24900(9) 0.0180(6) Uani 1 1 d . . . . .
H1A H 1.1567 1.1851 0.2444 0.022 Uiso 1 1 calc R U . . .
C1B C 0.4704(6) 0.5541(4) 0.29231(11) 0.0185(7) Uani 1 1 d . . . . .
C2B C 0.6147(6) 0.5188(5) 0.32599(11) 0.0190(7) Uani 1 1 d . . . . .
H2B H 0.7551 0.4621 0.3200 0.023 Uiso 1 1 calc R U . . .
C3B C 0.5588(6) 0.5645(4) 0.36858(11) 0.0199(8) Uani 1 1 d . . . . .
C4B C 0.7059(6) 0.5317(5) 0.40358(12) 0.0215(8) Uani 1 1 d . . . . .
H4B H 0.8477 0.4764 0.3981 0.026 Uiso 1 1 calc R U . . .
C5B C 0.6475(6) 0.5780(5) 0.44475(12) 0.0259(8) Uani 1 1 d . . . . .
H5B H 0.7486 0.5547 0.4676 0.031 Uiso 1 1 calc R U . . .
C6B C 0.4368(7) 0.6608(5) 0.45374(12) 0.0265(9) Uani 1 1 d . . . . .
H6B H 0.3972 0.6925 0.4826 0.032 Uiso 1 1 calc R U . . .
C7B C 0.2898(6) 0.6954(5) 0.42085(12) 0.0237(8) Uani 1 1 d . . . . .
H7B H 0.1496 0.7518 0.4271 0.028 Uiso 1 1 calc R U . . .
C8B C 0.3447(6) 0.6481(4) 0.37802(11) 0.0181(7) Uani 1 1 d . . . . .
C9B C 0.1995(6) 0.6798(5) 0.34317(11) 0.0195(8) Uani 1 1 d . . . . .
H9B H 0.0573 0.7340 0.3489 0.023 Uiso 1 1 calc R U . . .
C10B C 0.2551(6) 0.6355(5) 0.30105(11) 0.0189(8) Uani 1 1 d . . . . .
C11B C 0.1071(6) 0.6724(5) 0.26555(12) 0.0204(8) Uani 1 1 d . . . . .
H11B H -0.0396 0.7175 0.2716 0.025 Uiso 1 1 calc R U . . .
C12B C 0.1672(6) 0.6460(5) 0.22428(11) 0.0202(8) Uani 1 1 d . . . . .
H12B H 0.0659 0.6752 0.2019 0.024 Uiso 1 1 calc R U . . .
C13B C 0.5021(6) 0.5462(5) 0.16771(11) 0.0199(8) Uani 1 1 d . . . . .
C14B C 0.7071(6) 0.4599(5) 0.15911(11) 0.0216(8) Uani 1 1 d . . . . .
H14B H 0.7890 0.4116 0.1820 0.026 Uiso 1 1 calc R U . . .
C15B C 0.7947(6) 0.4425(5) 0.11830(12) 0.0242(8) Uani 1 1 d . . . . .
H15B H 0.9352 0.3838 0.1137 0.029 Uiso 1 1 calc R U . . .
C16B C 0.6779(6) 0.5105(5) 0.08379(12) 0.0238(8) Uani 1 1 d . . . . .
C17B C 0.4748(6) 0.5969(5) 0.09212(12) 0.0265(9) Uani 1 1 d . . . . .
H17B H 0.3937 0.6452 0.0692 0.032 Uiso 1 1 calc R U . . .
C18B C 0.3866(6) 0.6150(5) 0.13286(11) 0.0231(8) Uani 1 1 d . . . . .
H18B H 0.2465 0.6745 0.1373 0.028 Uiso 1 1 calc R U . . .
C19B C 0.7756(8) 0.4895(6) 0.03978(13) 0.0376(11) Uani 1 1 d . . . . .
H19D H 0.9399 0.5053 0.0419 0.056 Uiso 1 1 calc R U . . .
H19E H 0.7104 0.5797 0.0221 0.056 Uiso 1 1 calc R U . . .
H19F H 0.7403 0.3697 0.0266 0.056 Uiso 1 1 calc R U . . .
B1B B 0.4023(7) 0.5678(5) 0.21374(13) 0.0214(9) Uani 1 1 d . . . . .
N1B N 0.5299(5) 0.5186(4) 0.24983(9) 0.0189(7) Uani 1 1 d . . . . .
H1B H 0.6572 0.4608 0.2449 0.023 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A N1A 1.383(4) . ?
C1A C2A 1.396(5) . ?
C1A C10A 1.438(5) . ?
C2A C3A 1.393(5) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.423(5) . ?
C3A C8A 1.439(5) . ?
C4A C5A 1.372(5) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.409(5) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.368(5) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.407(5) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.396(5) . ?
C9A C10A 1.382(5) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.444(5) . ?
C11A C12A 1.335(5) . ?
C11A H11A 0.9500 . ?
C12A B1A 1.550(5) . ?
C12A H12A 0.9500 . ?
C13A C18A 1.403(5) . ?
C13A C14A 1.408(5) . ?
C13A B1A 1.554(5) . ?
C14A C15A 1.391(5) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.386(5) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.401(5) . ?
C16A C19A 1.493(5) . ?
C17A C18A 1.388(5) . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9500 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
B1A N1A 1.421(5) . ?
N1A H1A 0.8800 . ?
C1B C2B 1.385(5) . ?
C1B N1B 1.390(4) . ?
C1B C10B 1.437(5) . ?
C2B C3B 1.399(5) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.422(5) . ?
C3B C8B 1.441(5) . ?
C4B C5B 1.362(5) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.418(5) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.374(5) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.406(5) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.410(5) . ?
C9B C10B 1.382(5) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.444(5) . ?
C11B C12B 1.348(5) . ?
C11B H11B 0.9500 . ?
C12B B1B 1.544(5) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.398(5) . ?
C13B C18B 1.407(5) . ?
C13B B1B 1.567(5) . ?
C14B C15B 1.387(5) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.399(5) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.387(5) . ?
C16B C19B 1.503(5) . ?
C17B C18B 1.386(5) . ?
C17B H17B 0.9500 . ?
C18B H18B 0.9500 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
B1B N1B 1.418(5) . ?
N1B H1B 0.8800 . ?

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
N1A C1A C2A 122.4(3) . . ?
N1A C1A C10A 118.7(3) . . ?
C2A C1A C10A 118.8(3) . . ?
C3A C2A C1A 121.7(3) . . ?
C3A C2A H2A 119.2 . . ?
C1A C2A H2A 119.2 . . ?
C2A C3A C4A 122.1(3) . . ?
C2A C3A C8A 119.6(3) . . ?
C4A C3A C8A 118.2(3) . . ?
C5A C4A C3A 120.5(4) . . ?
C5A C4A H4A 119.8 . . ?
C3A C4A H4A 119.8 . . ?
C4A C5A C6A 120.9(4) . . ?
C4A C5A H5A 119.5 . . ?
C6A C5A H5A 119.5 . . ?
C7A C6A C5A 120.0(4) . . ?
C7A C6A H6A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C6A C7A C8A 121.2(4) . . ?
C6A C7A H7A 119.4 . . ?
C8A C7A H7A 119.4 . . ?
C9A C8A C7A 122.8(3) . . ?
C9A C8A C3A 118.0(3) . . ?
C7A C8A C3A 119.2(3) . . ?
C10A C9A C8A 122.7(3) . . ?
C10A C9A H9A 118.6 . . ?
C8A C9A H9A 118.6 . . ?
C9A C10A C1A 119.1(3) . . ?
C9A C10A C11A 122.4(3) . . ?
C1A C10A C11A 118.5(3) . . ?
C12A C11A C10A 123.8(3) . . ?
C12A C11A H11A 118.1 . . ?
C10A C11A H11A 118.1 . . ?
C11A C12A B1A 118.9(3) . . ?
C11A C12A H12A 120.6 . . ?
B1A C12A H12A 120.6 . . ?
C18A C13A C14A 116.0(3) . . ?
C18A C13A B1A 121.3(3) . . ?
C14A C13A B1A 122.6(3) . . ?
C15A C14A C13A 122.1(3) . . ?
C15A C14A H14A 119.0 . . ?
C13A C14A H14A 119.0 . . ?
C16A C15A C14A 121.1(4) . . ?
C16A C15A H15A 119.4 . . ?
C14A C15A H15A 119.4 . . ?
C15A C16A C17A 117.8(4) . . ?
C15A C16A C19A 120.6(4) . . ?
C17A C16A C19A 121.7(4) . . ?
C18A C17A C16A 121.1(4) . . ?
C18A C17A H17A 119.5 . . ?
C16A C17A H17A 119.5 . . ?
C17A C18A C13A 122.0(4) . . ?
C17A C18A H18A 119.0 . . ?
C13A C18A H18A 119.0 . . ?
C16A C19A H19A 109.5 . . ?
C16A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C16A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
N1A B1A C12A 114.7(3) . . ?
N1A B1A C13A 121.1(3) . . ?
C12A B1A C13A 124.2(3) . . ?
C1A N1A B1A 125.0(3) . . ?
C1A N1A H1A 117.5 . . ?
B1A N1A H1A 117.5 . . ?
C2B C1B N1B 122.0(3) . . ?
C2B C1B C10B 119.6(3) . . ?
N1B C1B C10B 118.3(3) . . ?
C1B C2B C3B 121.6(3) . . ?
C1B C2B H2B 119.2 . . ?
C3B C2B H2B 119.2 . . ?
C2B C3B C4B 122.5(3) . . ?
C2B C3B C8B 119.6(3) . . ?
C4B C3B C8B 117.9(3) . . ?
C5B C4B C3B 121.3(3) . . ?
C5B C4B H4B 119.3 . . ?
C3B C4B H4B 119.3 . . ?
C4B C5B C6B 120.5(3) . . ?
C4B C5B H5B 119.8 . . ?
C6B C5B H5B 119.8 . . ?
C7B C6B C5B 120.1(3) . . ?
C7B C6B H6B 119.9 . . ?
C5B C6B H6B 119.9 . . ?
C6B C7B C8B 120.8(3) . . ?
C6B C7B H7B 119.6 . . ?
C8B C7B H7B 119.6 . . ?
C7B C8B C9B 123.0(3) . . ?
C7B C8B C3B 119.5(3) . . ?
C9B C8B C3B 117.5(3) . . ?
C10B C9B C8B 122.9(3) . . ?
C10B C9B H9B 118.6 . . ?
C8B C9B H9B 118.6 . . ?
C9B C10B C1B 118.7(3) . . ?
C9B C10B C11B 122.4(3) . . ?
C1B C10B C11B 118.9(3) . . ?
C12B C11B C10B 123.2(3) . . ?
C12B C11B H11B 118.4 . . ?
C10B C11B H11B 118.4 . . ?
C11B C12B B1B 119.2(3) . . ?
C11B C12B H12B 120.4 . . ?
B1B C12B H12B 120.4 . . ?
C14B C13B C18B 116.9(3) . . ?
C14B C13B B1B 122.5(3) . . ?
C18B C13B B1B 120.6(3) . . ?
C15B C14B C13B 122.1(3) . . ?
C15B C14B H14B 119.0 . . ?
C13B C14B H14B 119.0 . . ?
C14B C15B C16B 120.6(3) . . ?
C14B C15B H15B 119.7 . . ?
C16B C15B H15B 119.7 . . ?
C17B C16B C15B 117.6(3) . . ?
C17B C16B C19B 122.7(3) . . ?
C15B C16B C19B 119.7(3) . . ?
C18B C17B C16B 122.1(3) . . ?
C18B C17B H17B 119.0 . . ?
C16B C17B H17B 119.0 . . ?
C17B C18B C13B 120.7(3) . . ?
C17B C18B H18B 119.6 . . ?
C13B C18B H18B 119.6 . . ?
C16B C19B H19D 109.5 . . ?
C16B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C16B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
N1B B1B C12B 114.5(3) . . ?
N1B B1B C13B 120.9(3) . . ?
C12B B1B C13B 124.6(3) . . ?
C1B N1B B1B 125.3(3) . . ?
C1B N1B H1B 117.3 . . ?
B1B N1B H1B 117.3 . . ?

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
N1A C1A C2A C3A -177.0(3) . . . . ?
C10A C1A C2A C3A 0.9(5) . . . . ?
C1A C2A C3A C4A 178.5(3) . . . . ?
C1A C2A C3A C8A 0.1(5) . . . . ?
C2A C3A C4A C5A 179.9(3) . . . . ?
C8A C3A C4A C5A -1.6(5) . . . . ?
C3A C4A C5A C6A 1.2(5) . . . . ?
C4A C5A C6A C7A -0.3(5) . . . . ?
C5A C6A C7A C8A -0.1(5) . . . . ?
C6A C7A C8A C9A -179.0(3) . . . . ?
C6A C7A C8A C3A -0.3(5) . . . . ?
C2A C3A C8A C9A -1.6(5) . . . . ?
C4A C3A C8A C9A 179.9(3) . . . . ?
C2A C3A C8A C7A 179.7(3) . . . . ?
C4A C3A C8A C7A 1.1(5) . . . . ?
C7A C8A C9A C10A -179.1(3) . . . . ?
C3A C8A C9A C10A 2.2(5) . . . . ?
C8A C9A C10A C1A -1.3(5) . . . . ?
C8A C9A C10A C11A 177.9(3) . . . . ?
N1A C1A C10A C9A 177.6(3) . . . . ?
C2A C1A C10A C9A -0.3(5) . . . . ?
N1A C1A C10A C11A -1.5(4) . . . . ?
C2A C1A C10A C11A -179.5(3) . . . . ?
C9A C10A C11A C12A -174.6(3) . . . . ?
C1A C10A C11A C12A 4.5(5) . . . . ?
C10A C11A C12A B1A -1.3(5) . . . . ?
C18A C13A C14A C15A 0.4(5) . . . . ?
B1A C13A C14A C15A 179.1(3) . . . . ?
C13A C14A C15A C16A 0.0(5) . . . . ?
C14A C15A C16A C17A -0.4(5) . . . . ?
C14A C15A C16A C19A 179.4(3) . . . . ?
C15A C16A C17A C18A 0.4(5) . . . . ?
C19A C16A C17A C18A -179.4(3) . . . . ?
C16A C17A C18A C13A 0.0(5) . . . . ?
C14A C13A C18A C17A -0.4(5) . . . . ?
B1A C13A C18A C17A -179.1(3) . . . . ?
C11A C12A B1A N1A -4.6(5) . . . . ?
C11A C12A B1A C13A 174.6(3) . . . . ?
C18A C13A B1A N1A 172.0(3) . . . . ?
C14A C13A B1A N1A -6.6(5) . . . . ?
C18A C13A B1A C12A -7.1(5) . . . . ?
C14A C13A B1A C12A 174.3(3) . . . . ?
C2A C1A N1A B1A 173.0(3) . . . . ?
C10A C1A N1A B1A -4.9(5) . . . . ?
C12A B1A N1A C1A 7.8(5) . . . . ?
C13A B1A N1A C1A -171.4(3) . . . . ?
N1B C1B C2B C3B 176.2(3) . . . . ?
C10B C1B C2B C3B -1.6(5) . . . . ?
C1B C2B C3B C4B -179.1(3) . . . . ?
C1B C2B C3B C8B 0.9(5) . . . . ?
C2B C3B C4B C5B 179.8(3) . . . . ?
C8B C3B C4B C5B -0.2(5) . . . . ?
C3B C4B C5B C6B 0.0(5) . . . . ?
C4B C5B C6B C7B -0.2(6) . . . . ?
C5B C6B C7B C8B 0.6(6) . . . . ?
C6B C7B C8B C9B 179.7(3) . . . . ?
C6B C7B C8B C3B -0.8(5) . . . . ?
C2B C3B C8B C7B -179.4(3) . . . . ?
C4B C3B C8B C7B 0.6(5) . . . . ?
C2B C3B C8B C9B 0.1(5) . . . . ?
C4B C3B C8B C9B -179.8(3) . . . . ?
C7B C8B C9B C10B 179.1(3) . . . . ?
C3B C8B C9B C10B -0.5(5) . . . . ?
C8B C9B C10B C1B -0.2(5) . . . . ?
C8B C9B C10B C11B -178.5(3) . . . . ?
C2B C1B C10B C9B 1.3(5) . . . . ?
N1B C1B C10B C9B -176.7(3) . . . . ?
C2B C1B C10B C11B 179.6(3) . . . . ?
N1B C1B C10B C11B 1.7(5) . . . . ?
C9B C10B C11B C12B 173.4(3) . . . . ?
C1B C10B C11B C12B -4.9(5) . . . . ?
C10B C11B C12B B1B 1.7(5) . . . . ?
C18B C13B C14B C15B 0.2(5) . . . . ?
B1B C13B C14B C15B -179.5(3) . . . . ?
C13B C14B C15B C16B -0.5(6) . . . . ?
C14B C15B C16B C17B 0.8(6) . . . . ?
C14B C15B C16B C19B -179.7(4) . . . . ?
C15B C16B C17B C18B -0.7(6) . . . . ?
C19B C16B C17B C18B 179.9(4) . . . . ?
C16B C17B C18B C13B 0.3(6) . . . . ?
C14B C13B C18B C17B -0.1(5) . . . . ?
B1B C13B C18B C17B 179.7(3) . . . . ?
C11B C12B B1B N1B 4.2(5) . . . . ?
C11B C12B B1B C13B -174.3(3) . . . . ?
C14B C13B B1B N1B 7.5(5) . . . . ?
C18B C13B B1B N1B -172.2(3) . . . . ?
C14B C13B B1B C12B -174.1(3) . . . . ?
C18B C13B B1B C12B 6.2(5) . . . . ?
C2B C1B N1B B1B -173.0(3) . . . . ?
C10B C1B N1B B1B 4.9(5) . . . . ?
C12B B1B N1B C1B -7.7(5) . . . . ?
C13B B1B N1B C1B 170.9(3) . . . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.074

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1435442'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 B N'
_chemical_formula_sum            'C18 H14 B N'
_chemical_formula_weight         255.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   7.5827(3)
_cell_length_b                   5.8864(3)
_cell_length_c                   14.3622(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.408(4)
_cell_angle_gamma                90
_cell_volume                     639.92(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4047
_cell_measurement_theta_min      5.81
_cell_measurement_theta_max      72.14

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.576
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            7322
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.082
_diffrn_reflns_theta_max         71.899
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.912
_reflns_number_total             2277
_reflns_number_gt                2191
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_max     0.799
_reflns_Friedel_fraction_full    0.806

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0622P)²+0.0737P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 846 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
# the absolute structure parameter is meaningless because the compound is a weak anomalous scatterer.
_refine_ls_abs_structure_Flack   .
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2277
_refine_ls_number_parameters     188
_refine_ls_number_restraints     757
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      0.908
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2348(2) 0.5498(4) 0.55864(13) 0.0178(4) Uani 0.8954(15) 1 d . U P A 1
C2 C 0.2102(2) 0.7028(4) 0.62926(12) 0.0181(4) Uani 0.8954(15) 1 d . U P A 1
H2 H 0.1478 0.8400 0.6158 0.022 Uiso 0.8954(15) 1 calc R U P A 1
C3 C 0.2766(2) 0.6583(3) 0.72125(13) 0.0191(4) Uani 0.8954(15) 1 d . U P A 1
C4 C 0.2560(2) 0.8157(4) 0.79528(13) 0.0208(4) Uani 0.8954(15) 1 d . U P A 1
H4 H 0.1943 0.9541 0.7833 0.025 Uiso 0.8954(15) 1 calc R U P A 1
C5 C 0.3246(3) 0.7690(4) 0.88356(14) 0.0239(5) Uani 0.8954(15) 1 d . U P A 1
H5 H 0.3095 0.8752 0.9323 0.029 Uiso 0.8954(15) 1 calc R U P A 1
C6 C 0.4176(3) 0.5647(4) 0.90314(13) 0.0258(5) Uani 0.8954(15) 1 d . U P A 1
H6 H 0.4653 0.5354 0.9646 0.031 Uiso 0.8954(15) 1 calc R U P A 1
C7 C 0.4391(2) 0.4088(4) 0.83407(13) 0.0234(4) Uani 0.8954(15) 1 d . U P A 1
H7 H 0.5017 0.2720 0.8480 0.028 Uiso 0.8954(15) 1 calc R U P A 1
C8 C 0.3683(2) 0.4502(3) 0.74119(13) 0.0202(4) Uani 0.8954(15) 1 d . U P A 1
C9 C 0.3855(2) 0.2933(3) 0.66892(13) 0.0200(4) Uani 0.8954(15) 1 d . U P A 1
H9 H 0.4427 0.1525 0.6822 0.024 Uiso 0.8954(15) 1 calc R U P A 1
C10 C 0.3209(2) 0.3386(3) 0.57823(13) 0.0182(4) Uani 0.8954(15) 1 d . U P A 1
C11 C 0.3466(2) 0.1776(4) 0.50373(13) 0.0198(4) Uani 0.8954(15) 1 d . U P A 1
H11 H 0.3988 0.0344 0.5186 0.024 Uiso 0.8954(15) 1 calc R U P A 1
C12 C 0.2983(2) 0.2259(4) 0.41353(13) 0.0213(4) Uani 0.8954(15) 1 d . U P A 1
H12 H 0.3165 0.1171 0.3662 0.026 Uiso 0.8954(15) 1 calc R U P A 1
C13 C 0.1698(2) 0.5384(4) 0.28490(13) 0.0193(4) Uani 0.8954(15) 1 d . U P A 1
C14 C 0.0848(2) 0.7453(3) 0.26234(13) 0.0207(4) Uani 0.8954(15) 1 d . U P A 1
H14 H 0.0527 0.8433 0.3111 0.025 Uiso 0.8954(15) 1 calc R U P A 1
C15 C 0.0465(2) 0.8097(4) 0.16990(14) 0.0236(5) Uani 0.8954(15) 1 d . U P A 1
H15 H -0.0116 0.9499 0.1564 0.028 Uiso 0.8954(15) 1 calc R U P A 1
C16 C 0.0930(3) 0.6697(4) 0.09740(13) 0.0250(5) Uani 0.8954(15) 1 d . U P A 1
H16 H 0.0662 0.7131 0.0344 0.030 Uiso 0.8954(15) 1 calc R U P A 1
C17 C 0.1796(3) 0.4643(4) 0.11794(14) 0.0253(5) Uani 0.8954(15) 1 d . U P A 1
H17 H 0.2130 0.3681 0.0689 0.030 Uiso 0.8954(15) 1 calc R U P A 1
C18 C 0.2167(2) 0.4014(4) 0.21023(13) 0.0218(4) Uani 0.8954(15) 1 d . U P A 1
H18 H 0.2756 0.2615 0.2232 0.026 Uiso 0.8954(15) 1 calc R U P A 1
B1 B 0.2138(3) 0.4574(4) 0.38784(15) 0.0192(4) Uani 0.8954(15) 1 d . U P A 1
N1 N 0.18213(19) 0.5989(3) 0.46570(10) 0.0184(4) Uani 0.8954(15) 1 d . U P A 1
H1 H 0.1251 0.7271 0.4545 0.022 Uiso 0.8954(15) 1 calc R U P A 1
C1' C 0.2021(6) 0.5420(12) 0.4410(4) 0.0178(4) Uani 0.1046(15) 1 d G U P A 2
C2' C 0.1327(8) 0.6967(13) 0.3786(4) 0.0181(4) Uani 0.1046(15) 1 d G U P A 2
H2' H 0.0845 0.8353 0.3995 0.022 Uiso 0.1046(15) 1 d G U P A 2
C3' C 0.1336(8) 0.6483(14) 0.2831(4) 0.0191(4) Uani 0.1046(15) 1 d G U P A 2
C4' C 0.0694(11) 0.8082(16) 0.2162(5) 0.0208(4) Uani 0.1046(15) 1 d G U P A 2
H4' H 0.0252 0.9494 0.2368 0.025 Uiso 0.1046(15) 1 d G U P A 2
C5' C 0.0690(11) 0.7665(18) 0.1247(5) 0.0239(5) Uani 0.1046(15) 1 d G U P A 2
H5' H 0.0256 0.8758 0.0803 0.029 Uiso 0.1046(15) 1 d G U P A 2
C6' C 0.1345(10) 0.5567(18) 0.0961(4) 0.0258(5) Uani 0.1046(15) 1 d G U P A 2
H6' H 0.1283 0.5203 0.0316 0.031 Uiso 0.1046(15) 1 d G U P A 2
C7' C 0.2054(10) 0.4067(17) 0.1573(4) 0.0234(4) Uani 0.1046(15) 1 d G U P A 2
H7' H 0.2577 0.2716 0.1355 0.028 Uiso 0.1046(15) 1 d G U P A 2
C8' C 0.2030(8) 0.4474(15) 0.2534(4) 0.0202(4) Uani 0.1046(15) 1 d G U P A 2
C9' C 0.2698(9) 0.2841(14) 0.3195(4) 0.0200(4) Uani 0.1046(15) 1 d G U P A 2
H9' H 0.3150 0.1434 0.2989 0.024 Uiso 0.1046(15) 1 d G U P A 2
C10' C 0.2686(8) 0.3305(13) 0.4121(4) 0.0182(4) Uani 0.1046(15) 1 d G U P A 2
C11' C 0.3293(11) 0.1701(13) 0.4816(5) 0.0198(4) Uani 0.1046(15) 1 d G U P A 2
H11' H 0.3536 0.0196 0.4621 0.024 Uiso 0.1046(15) 1 d G U P A 2
C12' C 0.3542(10) 0.2200(13) 0.5737(4) 0.0213(4) Uani 0.1046(15) 1 d G U P A 2
H12' H 0.4098 0.1127 0.6153 0.026 Uiso 0.1046(15) 1 d G U P A 2
C13' C 0.3229(8) 0.5346(15) 0.7166(4) 0.0193(4) Uani 0.1046(15) 1 d G U P A 2
C14' C 0.2575(10) 0.7381(15) 0.7478(4) 0.0207(4) Uani 0.1046(15) 1 d G U P A 2
H14' H 0.1927 0.8341 0.7050 0.025 Uiso 0.1046(15) 1 d G U P A 2
C15' C 0.2842(12) 0.8057(18) 0.8399(4) 0.0236(5) Uani 0.1046(15) 1 d G U P A 2
H15' H 0.2383 0.9460 0.8604 0.028 Uiso 0.1046(15) 1 d G U P A 2
C16' C 0.3765(11) 0.6687(19) 0.8997(4) 0.0250(5) Uani 0.1046(15) 1 d G U P A 2
H16' H 0.3937 0.7126 0.9632 0.030 Uiso 0.1046(15) 1 d G U P A 2
C17' C 0.4468(10) 0.4654(19) 0.8711(4) 0.0253(5) Uani 0.1046(15) 1 d G U P A 2
H17' H 0.5139 0.3710 0.9135 0.030 Uiso 0.1046(15) 1 d G U P A 2
C18' C 0.4162(9) 0.4045(16) 0.7789(4) 0.0218(4) Uani 0.1046(15) 1 d G U P A 2
H18' H 0.4631 0.2647 0.7584 0.026 Uiso 0.1046(15) 1 d G U P A 2
B1' B 0.2934(7) 0.4468(13) 0.6104(4) 0.0192(4) Uani 0.1046(15) 1 d G U P A 2
N1' N 0.2095(6) 0.5799(12) 0.5365(4) 0.0184(4) Uani 0.1046(15) 1 d G U P A 2
H1' H 0.1550 0.7030 0.5544 0.022 Uiso 0.1046(15) 1 d G U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.377(3) . ?
C1 N1 1.401(2) . ?
C1 C10 1.424(3) . ?
C2 C3 1.410(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.426(3) . ?
C3 C8 1.429(3) . ?
C4 C5 1.369(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.414(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.368(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.429(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.401(3) . ?
C9 C10 1.390(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.451(3) . ?
C11 C12 1.355(3) . ?
C11 H11 0.9500 . ?
C12 B1 1.541(3) . ?
C12 H12 0.9500 . ?
C13 C18 1.405(3) . ?
C13 C14 1.407(3) . ?
C13 B1 1.570(3) . ?
C14 C15 1.394(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.399(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
B1 N1 1.426(3) . ?
N1 H1 0.8800 . ?
C1' C2' 1.3618 . ?
C1' N1' 1.3872 . ?
C1' C10' 1.4149 . ?
C2' C3' 1.4016 . ?
C2' H2' 0.9500 . ?
C3' C8' 1.3729 . ?
C3' C4' 1.4101 . ?
C4' C5' 1.3375 . ?
C4' H4' 0.9500 . ?
C5' C6' 1.4016 . ?
C5' H5' 0.9500 . ?
C6' C7' 1.3355 . ?
C6' H6' 0.9500 . ?
C7' C8' 1.4020 . ?
C7' H7' 0.9500 . ?
C8' C9' 1.4228 . ?
C9' C10' 1.3592 . ?
C9' H9' 0.9500 . ?
C10' C11' 1.4292 . ?
C11' C12' 1.3575 . ?
C11' H11' 0.9500 . ?
C12' B1' 1.5170 . ?
C12' H12' 0.9500 . ?
C13' C18' 1.3464 . ?
C13' C14' 1.3816 . ?
C13' B1' 1.6131 . ?
C14' C15' 1.3842 . ?
C14' H14' 0.9500 . ?
C15' C16' 1.3441 . ?
C15' H15' 0.9500 . ?
C16' C17' 1.3827 . ?
C16' H16' 0.9500 . ?
C17' C18' 1.3781 . ?
C17' H17' 0.9500 . ?
C18' H18' 0.9500 . ?
B1' N1' 1.4367 . ?
N1' H1' 0.8800 . ?

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
C2 C1 N1 121.57(18) . . ?
C2 C1 C10 120.37(16) . . ?
N1 C1 C10 118.02(17) . . ?
C1 C2 C3 120.81(18) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 121.95(18) . . ?
C2 C3 C8 119.29(18) . . ?
C4 C3 C8 118.76(17) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.83(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.39(18) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 122.21(19) . . ?
C9 C8 C3 118.82(17) . . ?
C7 C8 C3 118.98(19) . . ?
C10 C9 C8 121.65(18) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C1 118.98(17) . . ?
C9 C10 C11 120.67(18) . . ?
C1 C10 C11 120.31(16) . . ?
C12 C11 C10 121.80(19) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 B1 119.95(18) . . ?
C11 C12 H12 120.0 . . ?
B1 C12 H12 120.0 . . ?
C18 C13 C14 117.05(17) . . ?
C18 C13 B1 119.68(17) . . ?
C14 C13 B1 123.27(17) . . ?
C15 C14 C13 121.40(18) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.42(18) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 119.84(19) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C13 122.0(2) . . ?
C17 C18 H18 119.0 . . ?
C13 C18 H18 119.0 . . ?
N1 B1 C12 114.57(17) . . ?
N1 B1 C13 121.63(17) . . ?
C12 B1 C13 123.78(17) . . ?
C1 N1 B1 125.10(17) . . ?
C1 N1 H1 117.5 . . ?
B1 N1 H1 117.5 . . ?
C2' C1' N1' 122.3 . . ?
C2' C1' C10' 121.7 . . ?
N1' C1' C10' 115.9 . . ?
C1' C2' C3' 119.0 . . ?
C1' C2' H2' 120.5 . . ?
C3' C2' H2' 120.5 . . ?
C8' C3' C2' 120.2 . . ?
C8' C3' C4' 119.1 . . ?
C2' C3' C4' 120.6 . . ?
C5' C4' C3' 121.8 . . ?
C5' C4' H4' 119.1 . . ?
C3' C4' H4' 119.1 . . ?
C4' C5' C6' 118.0 . . ?
C4' C5' H5' 121.0 . . ?
C6' C5' H5' 121.0 . . ?
C7' C6' C5' 121.8 . . ?
C7' C6' H6' 119.1 . . ?
C5' C6' H6' 119.1 . . ?
C6' C7' C8' 120.4 . . ?
C6' C7' H7' 119.8 . . ?
C8' C7' H7' 119.8 . . ?
C3' C8' C7' 118.7 . . ?
C3' C8' C9' 120.2 . . ?
C7' C8' C9' 121.1 . . ?
C10' C9' C8' 119.7 . . ?
C10' C9' H9' 120.2 . . ?
C8' C9' H9' 120.2 . . ?
C9' C10' C1' 119.1 . . ?
C9' C10' C11' 122.0 . . ?
C1' C10' C11' 118.8 . . ?
C12' C11' C10' 123.9 . . ?
C12' C11' H11' 118.1 . . ?
C10' C11' H11' 118.1 . . ?
C11' C12' B1' 120.1 . . ?
C11' C12' H12' 120.0 . . ?
B1' C12' H12' 119.9 . . ?
C18' C13' C14' 117.5 . . ?
C18' C13' B1' 119.0 . . ?
C14' C13' B1' 123.5 . . ?
C13' C14' C15' 121.6 . . ?
C13' C14' H14' 119.2 . . ?
C15' C14' H14' 119.2 . . ?
C16' C15' C14' 118.6 . . ?
C16' C15' H15' 120.7 . . ?
C14' C15' H15' 120.7 . . ?
C15' C16' C17' 121.6 . . ?
C15' C16' H16' 119.2 . . ?
C17' C16' H16' 119.2 . . ?
C18' C17' C16' 117.7 . . ?
C18' C17' H17' 121.2 . . ?
C16' C17' H17' 121.2 . . ?
C13' C18' C17' 122.9 . . ?
C13' C18' H18' 118.6 . . ?
C17' C18' H18' 118.6 . . ?
N1' B1' C12' 110.7 . . ?
N1' B1' C13' 123.6 . . ?
C12' B1' C13' 125.6 . . ?
C1' N1' B1' 129.2 . . ?
C1' N1' H1' 115.4 . . ?
B1' N1' H1' 115.4 . . ?

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
N1 C1 C2 C3 -174.88(16) . . . . ?
C10 C1 C2 C3 2.9(3) . . . . ?
C1 C2 C3 C4 178.76(17) . . . . ?
C1 C2 C3 C8 -0.9(2) . . . . ?
C2 C3 C4 C5 -178.94(17) . . . . ?
C8 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C9 -179.07(18) . . . . ?
C6 C7 C8 C3 0.8(3) . . . . ?
C2 C3 C8 C9 -1.7(2) . . . . ?
C4 C3 C8 C9 178.71(17) . . . . ?
C2 C3 C8 C7 178.43(17) . . . . ?
C4 C3 C8 C7 -1.2(2) . . . . ?
C7 C8 C9 C10 -177.94(17) . . . . ?
C3 C8 C9 C10 2.2(3) . . . . ?
C8 C9 C10 C1 -0.1(3) . . . . ?
C8 C9 C10 C11 177.42(16) . . . . ?
C2 C1 C10 C9 -2.4(2) . . . . ?
N1 C1 C10 C9 175.45(16) . . . . ?
C2 C1 C10 C11 180.00(16) . . . . ?
N1 C1 C10 C11 -2.1(2) . . . . ?
C9 C10 C11 C12 -174.31(16) . . . . ?
C1 C10 C11 C12 3.2(3) . . . . ?
C10 C11 C12 B1 0.1(3) . . . . ?
C18 C13 C14 C15 0.9(2) . . . . ?
B1 C13 C14 C15 -179.32(17) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C13 0.0(3) . . . . ?
C14 C13 C18 C17 -0.8(3) . . . . ?
B1 C13 C18 C17 179.48(17) . . . . ?
C11 C12 B1 N1 -4.2(2) . . . . ?
C11 C12 B1 C13 174.01(16) . . . . ?
C18 C13 B1 N1 174.65(17) . . . . ?
C14 C13 B1 N1 -5.1(3) . . . . ?
C18 C13 B1 C12 -3.5(3) . . . . ?
C14 C13 B1 C12 176.80(16) . . . . ?
C2 C1 N1 B1 175.35(16) . . . . ?
C10 C1 N1 B1 -2.5(3) . . . . ?
C12 B1 N1 C1 5.5(3) . . . . ?
C13 B1 N1 C1 -172.75(16) . . . . ?
N1' C1' C2' C3' 178.5 . . . . ?
C10' C1' C2' C3' -2.4 . . . . ?
C1' C2' C3' C8' 0.2 . . . . ?
C1' C2' C3' C4' -177.5 . . . . ?
C8' C3' C4' C5' 2.2 . . . . ?
C2' C3' C4' C5' 179.9 . . . . ?
C3' C4' C5' C6' 0.2 . . . . ?
C4' C5' C6' C7' -4.0 . . . . ?
C5' C6' C7' C8' 5.3 . . . . ?
C2' C3' C8' C7' -178.6 . . . . ?
C4' C3' C8' C7' -0.8 . . . . ?
C2' C3' C8' C9' 1.8 . . . . ?
C4' C3' C8' C9' 179.5 . . . . ?
C6' C7' C8' C3' -2.8 . . . . ?
C6' C7' C8' C9' 176.8 . . . . ?
C3' C8' C9' C10' -1.6 . . . . ?
C7' C8' C9' C10' 178.8 . . . . ?
C8' C9' C10' C1' -0.5 . . . . ?
C8' C9' C10' C11' 178.1 . . . . ?
C2' C1' C10' C9' 2.6 . . . . ?
N1' C1' C10' C9' -178.3 . . . . ?
C2' C1' C10' C11' -176.1 . . . . ?
N1' C1' C10' C11' 3.0 . . . . ?
C9' C10' C11' C12' 170.2 . . . . ?
C1' C10' C11' C12' -11.1 . . . . ?
C10' C11' C12' B1' 8.6 . . . . ?
C18' C13' C14' C15' -0.9 . . . . ?
B1' C13' C14' C15' 179.2 . . . . ?
C13' C14' C15' C16' 0.1 . . . . ?
C14' C15' C16' C17' 1.0 . . . . ?
C15' C16' C17' C18' -1.3 . . . . ?
C14' C13' C18' C17' 0.6 . . . . ?
B1' C13' C18' C17' -179.5 . . . . ?
C16' C17' C18' C13' 0.5 . . . . ?
C11' C12' B1' N1' 1.4 . . . . ?
C11' C12' B1' C13' -176.7 . . . . ?
C18' C13' B1' N1' -174.4 . . . . ?
C14' C13' B1' N1' 5.4 . . . . ?
C18' C13' B1' C12' 3.4 . . . . ?
C14' C13' B1' C12' -176.7 . . . . ?
C2' C1' N1' B1' -173.0 . . . . ?
C10' C1' N1' B1' 8.0 . . . . ?
C12' B1' N1' C1' -10.1 . . . . ?
C13' B1' N1' C1' 168.1 . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.032

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 1435443'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 B F N'
_chemical_formula_sum            'C18 H13 B F N'
_chemical_formula_weight         273.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.5086(3)
_cell_length_b                   5.9024(3)
_cell_length_c                   29.5225(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.266(5)
_cell_angle_gamma                90
_cell_volume                     1306.28(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4217
_cell_measurement_theta_min      6.00
_cell_measurement_theta_max      71.98

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.716
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            8531
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.998
_diffrn_reflns_theta_max         71.875
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2569
_reflns_number_gt                2276
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0773P)²+0.7570P]
 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_number_reflns         2569
_refine_ls_number_parameters     380
_refine_ls_number_restraints     794
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      0.917
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9868(2) 0.3888(3) 0.28098(6) 0.0205(4) Uani 0.9619(15) 1 d D U P A 1
C2 C 0.9638(2) 0.5416(3) 0.31553(5) 0.0206(4) Uani 0.9619(15) 1 d D U P A 1
H2 H 0.9031 0.6801 0.3091 0.025 Uiso 0.9619(15) 1 calc R U P A 1
C3 C 1.0290(2) 0.4952(3) 0.36031(6) 0.0215(4) Uani 0.9619(15) 1 d D U P A 1
C4 C 1.0098(3) 0.6521(3) 0.39641(6) 0.0231(4) Uani 0.9619(15) 1 d D U P A 1
H4 H 0.9502 0.7919 0.3905 0.028 Uiso 0.9619(15) 1 calc R U P A 1
C5 C 1.0762(2) 0.6037(3) 0.43951(6) 0.0267(4) Uani 0.9619(15) 1 d D U P A 1
H5 H 1.0622 0.7100 0.4632 0.032 Uiso 0.9619(15) 1 calc R U P A 1
C6 C 1.1661(2) 0.3953(3) 0.44906(6) 0.0281(4) Uani 0.9619(15) 1 d D U P A 1
H6 H 1.2123 0.3635 0.4790 0.034 Uiso 0.9619(15) 1 calc R U P A 1
C7 C 1.1859(2) 0.2407(3) 0.41518(7) 0.0255(4) Uani 0.9619(15) 1 d D U P A 1
H7 H 1.2453 0.1016 0.4219 0.031 Uiso 0.9619(15) 1 calc R U P A 1
C8 C 1.1187(2) 0.2857(3) 0.37005(6) 0.0220(4) Uani 0.9619(15) 1 d D U P A 1
C9 C 1.1360(2) 0.1297(3) 0.33450(6) 0.0221(4) Uani 0.9619(15) 1 d D U P A 1
H9 H 1.1929 -0.0114 0.3409 0.027 Uiso 0.9619(15) 1 calc R U P A 1
C10 C 1.0727(2) 0.1755(3) 0.29059(6) 0.0206(4) Uani 0.9619(15) 1 d D U P A 1
C11 C 1.0966(2) 0.0166(3) 0.25404(6) 0.0215(4) Uani 0.9619(15) 1 d D U P A 1
H11 H 1.1483 -0.1268 0.2611 0.026 Uiso 0.9619(15) 1 calc R U P A 1
C12 C 1.0485(2) 0.0639(3) 0.21040(6) 0.0224(4) Uani 0.9619(15) 1 d D U P A 1
H12 H 1.0663 -0.0447 0.1874 0.027 Uiso 0.9619(15) 1 calc R U P A 1
B1 B 0.9640(2) 0.2965(3) 0.19811(6) 0.0213(4) Uani 0.9619(15) 1 d D U P A 1
N1 N 0.93362(17) 0.4380(2) 0.23591(5) 0.0210(3) Uani 0.9619(15) 1 d D U P A 1
H1 H 0.8769 0.5665 0.2305 0.025 Uiso 0.9619(15) 1 calc R U P A 1
C13 C 0.9197(2) 0.3778(3) 0.14811(6) 0.0220(4) Uani 0.9619(15) 1 d D U P A 1
C14 C 0.8347(2) 0.5848(3) 0.13699(6) 0.0236(4) Uani 0.9619(15) 1 d D U P A 1
H14 H 0.8009 0.6813 0.1608 0.028 Uiso 0.9619(15) 1 calc R U P A 1
C15 C 0.7987(2) 0.6522(3) 0.09232(6) 0.0249(4) Uani 0.9619(15) 1 d D U P A 1
H15 H 0.7411 0.7923 0.0854 0.030 Uiso 0.9619(15) 1 calc R U P A 1
C16 C 0.8488(2) 0.5103(4) 0.05836(6) 0.0261(4) Uani 0.9619(15) 1 d D U P A 1
C17 C 0.9342(2) 0.3057(3) 0.06669(6) 0.0263(4) Uani 0.9619(15) 1 d D U P A 1
H17 H 0.9680 0.2118 0.0425 0.032 Uiso 0.9619(15) 1 calc R U P A 1
C18 C 0.9688(2) 0.2419(3) 0.11163(6) 0.0242(4) Uani 0.9619(15) 1 d D U P A 1
H18 H 1.0277 0.1020 0.1180 0.029 Uiso 0.9619(15) 1 calc R U P A 1
F1 F 0.81252(15) 0.5739(2) 0.01462(4) 0.0364(3) Uani 0.9619(15) 1 d D U P A 1
C1' C 0.9492(15) 0.393(3) 0.2169(6) 0.021(3) Uani 0.0381(15) 1 d D U P A 2
C2' C 0.8817(17) 0.554(3) 0.1867(6) 0.024(3) Uani 0.0381(15) 1 d D U P A 2
H2' H 0.8377 0.6930 0.1976 0.029 Uiso 0.0381(15) 1 calc R U P A 2
C3' C 0.8782(15) 0.511(3) 0.1398(6) 0.023(2) Uani 0.0381(15) 1 d D U P A 2
C4' C 0.810(2) 0.672(4) 0.1077(8) 0.024(3) Uani 0.0381(15) 1 d D U P A 2
H4' H 0.7655 0.8124 0.1181 0.028 Uiso 0.0381(15) 1 calc R U P A 2
C5' C 0.807(3) 0.631(5) 0.0620(8) 0.028(3) Uani 0.0381(15) 1 d D U P A 2
H5' H 0.7603 0.7406 0.0410 0.033 Uiso 0.0381(15) 1 calc R U P A 2
C6' C 0.873(3) 0.421(5) 0.0465(7) 0.031(3) Uani 0.0381(15) 1 d D U P A 2
H6' H 0.8712 0.3909 0.0148 0.037 Uiso 0.0381(15) 1 calc R U P A 2
C7' C 0.940(3) 0.262(5) 0.0764(7) 0.026(3) Uani 0.0381(15) 1 d D U P A 2
H7' H 0.9838 0.1224 0.0653 0.031 Uiso 0.0381(15) 1 calc R U P A 2
C8' C 0.945(2) 0.301(3) 0.1239(6) 0.024(2) Uani 0.0381(15) 1 d D U P A 2
C9' C 1.013(3) 0.140(3) 0.1553(6) 0.025(3) Uani 0.0381(15) 1 d D U P A 2
H9' H 1.0572 -0.0002 0.1447 0.030 Uiso 0.0381(15) 1 calc R U P A 2
C10' C 1.016(2) 0.181(3) 0.2014(6) 0.021(2) Uani 0.0381(15) 1 d D U P A 2
C11' C 1.086(3) 0.018(3) 0.2342(7) 0.021(3) Uani 0.0381(15) 1 d D U P A 2
H11' H 1.1300 -0.1223 0.2235 0.025 Uiso 0.0381(15) 1 calc R U P A 2
C12' C 1.091(3) 0.054(4) 0.2793(7) 0.021(3) Uani 0.0381(15) 1 d D U P A 2
H12' H 1.1376 -0.0589 0.2996 0.026 Uiso 0.0381(15) 1 calc R U P A 2
B1' B 1.020(3) 0.279(4) 0.2981(6) 0.021(2) Uani 0.0381(15) 1 d D U P A 2
N1' N 0.957(5) 0.431(4) 0.2636(6) 0.018(3) Uani 0.0381(15) 1 d D U P A 2
H1' H 0.9182 0.5636 0.2726 0.021 Uiso 0.0381(15) 1 calc R U P A 2
C13' C 1.062(5) 0.364(5) 0.3482(7) 0.023(2) Uani 0.0381(15) 1 d D U P A 2
C14' C 1.002(6) 0.572(5) 0.3655(9) 0.023(3) Uani 0.0381(15) 1 d D U P A 2
H14' H 0.9343 0.6696 0.3456 0.027 Uiso 0.0381(15) 1 calc R U P A 2
C15' C 1.037(8) 0.640(6) 0.4101(9) 0.023(3) Uani 0.0381(15) 1 d D U P A 2
H15' H 0.9987 0.7829 0.4205 0.028 Uiso 0.0381(15) 1 calc R U P A 2
C16' C 1.130(5) 0.492(6) 0.4388(7) 0.026(3) Uani 0.0381(15) 1 d D U P A 2
C17' C 1.215(6) 0.303(6) 0.4229(9) 0.025(3) Uani 0.0381(15) 1 d D U P A 2
H17' H 1.3038 0.2251 0.4412 0.030 Uiso 0.0381(15) 1 calc R U P A 2
C18' C 1.166(6) 0.231(5) 0.3792(9) 0.024(3) Uani 0.0381(15) 1 d D U P A 2
H18' H 1.2043 0.0864 0.3697 0.028 Uiso 0.0381(15) 1 calc R U P A 2
F1' F 1.162(4) 0.551(5) 0.4828(7) 0.044(5) Uani 0.0381(15) 1 d D U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.380(2) . ?
C1 N1 1.398(2) . ?
C1 C10 1.436(2) . ?
C2 C3 1.410(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.425(2) . ?
C3 C8 1.429(2) . ?
C4 C5 1.370(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.423(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.368(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.423(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.408(2) . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.448(2) . ?
C11 C12 1.347(2) . ?
C11 H11 0.9500 . ?
C12 B1 1.547(2) . ?
C12 H12 0.9500 . ?
B1 N1 1.423(2) . ?
B1 C13 1.570(2) . ?
N1 H1 0.8800 . ?
C13 C18 1.409(2) . ?
C13 C14 1.409(2) . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9500 . ?
C16 F1 1.357(2) . ?
C16 C17 1.382(3) . ?
C17 C18 1.389(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C1' C2' 1.380(9) . ?
C1' N1' 1.395(9) . ?
C1' C10' 1.432(9) . ?
C2' C3' 1.406(10) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.420(10) . ?
C3' C8' 1.427(10) . ?
C4' C5' 1.368(10) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.422(10) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.366(10) . ?
C6' H6' 0.9500 . ?
C7' C8' 1.420(10) . ?
C7' H7' 0.9500 . ?
C8' C9' 1.403(10) . ?
C9' C10' 1.380(10) . ?
C9' H9' 0.9500 . ?
C10' C11' 1.444(10) . ?
C11' C12' 1.347(10) . ?
C11' H11' 0.9500 . ?
C12' B1' 1.545(10) . ?
C12' H12' 0.9500 . ?
B1' N1' 1.420(10) . ?
B1' C13' 1.576(9) . ?
N1' H1' 0.8800 . ?
C13' C18' 1.408(10) . ?
C13' C14' 1.408(10) . ?
C14' C15' 1.389(10) . ?
C14' H14' 0.9500 . ?
C15' C16' 1.374(10) . ?
C15' H15' 0.9500 . ?
C16' F1' 1.353(10) . ?
C16' C17' 1.384(10) . ?
C17' C18' 1.388(10) . ?
C17' H17' 0.9500 . ?
C18' H18' 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
C2 C1 N1 121.82(15) . . ?
C2 C1 C10 120.04(16) . . ?
N1 C1 C10 118.10(15) . . ?
C1 C2 C3 120.99(15) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 122.02(16) . . ?
C2 C3 C8 119.41(16) . . ?
C4 C3 C8 118.56(16) . . ?
C5 C4 C3 120.80(17) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.48(17) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.12(16) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.83(17) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 122.22(17) . . ?
C9 C8 C3 118.57(16) . . ?
C7 C8 C3 119.20(17) . . ?
C10 C9 C8 122.01(16) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C1 118.93(16) . . ?
C9 C10 C11 121.45(16) . . ?
C1 C10 C11 119.59(15) . . ?
C12 C11 C10 122.72(16) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C11 C12 B1 119.48(15) . . ?
C11 C12 H12 120.3 . . ?
B1 C12 H12 120.3 . . ?
N1 B1 C12 114.78(15) . . ?
N1 B1 C13 121.56(16) . . ?
C12 B1 C13 123.63(16) . . ?
C1 N1 B1 125.09(15) . . ?
C1 N1 H1 117.5 . . ?
B1 N1 H1 117.5 . . ?
C18 C13 C14 116.78(15) . . ?
C18 C13 B1 119.63(15) . . ?
C14 C13 B1 123.58(15) . . ?
C15 C14 C13 122.04(16) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C16 C15 C14 118.13(17) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
F1 C16 C15 118.48(18) . . ?
F1 C16 C17 118.46(18) . . ?
C15 C16 C17 123.06(17) . . ?
C16 C17 C18 117.79(17) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
C17 C18 C13 122.20(17) . . ?
C17 C18 H18 118.9 . . ?
C13 C18 H18 118.9 . . ?
C2' C1' N1' 121.3(12) . . ?
C2' C1' C10' 121.1(11) . . ?
N1' C1' C10' 117.6(10) . . ?
C1' C2' C3' 119.9(11) . . ?
C1' C2' H2' 120.0 . . ?
C3' C2' H2' 120.0 . . ?
C2' C3' C4' 121.6(12) . . ?
C2' C3' C8' 119.4(10) . . ?
C4' C3' C8' 118.9(11) . . ?
C5' C4' C3' 121.6(13) . . ?
C5' C4' H4' 119.2 . . ?
C3' C4' H4' 119.2 . . ?
C4' C5' C6' 119.2(13) . . ?
C4' C5' H5' 120.4 . . ?
C6' C5' H5' 120.4 . . ?
C7' C6' C5' 120.9(13) . . ?
C7' C6' H6' 119.5 . . ?
C5' C6' H6' 119.5 . . ?
C6' C7' C8' 121.0(13) . . ?
C6' C7' H7' 119.5 . . ?
C8' C7' H7' 119.5 . . ?
C9' C8' C7' 122.0(12) . . ?
C9' C8' C3' 119.6(11) . . ?
C7' C8' C3' 118.4(11) . . ?
C10' C9' C8' 121.1(12) . . ?
C10' C9' H9' 119.5 . . ?
C8' C9' H9' 119.5 . . ?
C9' C10' C1' 118.8(11) . . ?
C9' C10' C11' 122.0(12) . . ?
C1' C10' C11' 119.1(10) . . ?
C12' C11' C10' 123.1(13) . . ?
C12' C11' H11' 118.4 . . ?
C10' C11' H11' 118.4 . . ?
C11' C12' B1' 120.1(12) . . ?
C11' C12' H12' 119.9 . . ?
B1' C12' H12' 119.9 . . ?
N1' B1' C12' 113.2(10) . . ?
N1' B1' C13' 120.8(12) . . ?
C12' B1' C13' 123.9(11) . . ?
C1' N1' B1' 126.8(12) . . ?
C1' N1' H1' 116.6 . . ?
B1' N1' H1' 116.6 . . ?
C18' C13' C14' 115.2(11) . . ?
C18' C13' B1' 120.3(12) . . ?
C14' C13' B1' 124.5(12) . . ?
C15' C14' C13' 123.2(13) . . ?
C15' C14' H14' 118.4 . . ?
C13' C14' H14' 118.4 . . ?
C16' C15' C14' 117.6(13) . . ?
C16' C15' H15' 121.2 . . ?
C14' C15' H15' 121.2 . . ?
F1' C16' C15' 119.1(14) . . ?
F1' C16' C17' 118.1(14) . . ?
C15' C16' C17' 122.0(13) . . ?
C16' C17' C18' 117.1(14) . . ?
C16' C17' H17' 121.4 . . ?
C18' C17' H17' 121.4 . . ?
C17' C18' C13' 122.9(13) . . ?
C17' C18' H18' 118.5 . . ?
C13' C18' H18' 118.5 . . ?

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
N1 C1 C2 C3 -175.69(14) . . . . ?
C10 C1 C2 C3 2.2(2) . . . . ?
C1 C2 C3 C4 178.84(16) . . . . ?
C1 C2 C3 C8 -0.6(2) . . . . ?
C2 C3 C4 C5 -179.26(16) . . . . ?
C8 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C9 -179.58(16) . . . . ?
C6 C7 C8 C3 -0.2(3) . . . . ?
C2 C3 C8 C9 -1.2(2) . . . . ?
C4 C3 C8 C9 179.30(16) . . . . ?
C2 C3 C8 C7 179.36(15) . . . . ?
C4 C3 C8 C7 -0.1(2) . . . . ?
C7 C8 C9 C10 -179.08(15) . . . . ?
C3 C8 C9 C10 1.6(2) . . . . ?
C8 C9 C10 C1 0.0(2) . . . . ?
C8 C9 C10 C11 177.91(14) . . . . ?
C2 C1 C10 C9 -1.8(2) . . . . ?
N1 C1 C10 C9 176.08(13) . . . . ?
C2 C1 C10 C11 -179.82(14) . . . . ?
N1 C1 C10 C11 -1.9(2) . . . . ?
C9 C10 C11 C12 -174.82(15) . . . . ?
C1 C10 C11 C12 3.1(2) . . . . ?
C10 C11 C12 B1 0.0(2) . . . . ?
C11 C12 B1 N1 -4.0(2) . . . . ?
C11 C12 B1 C13 174.11(14) . . . . ?
C2 C1 N1 B1 175.32(15) . . . . ?
C10 C1 N1 B1 -2.6(2) . . . . ?
C12 B1 N1 C1 5.4(2) . . . . ?
C13 B1 N1 C1 -172.75(14) . . . . ?
N1 B1 C13 C18 173.46(14) . . . . ?
C12 B1 C13 C18 -4.5(2) . . . . ?
N1 B1 C13 C14 -5.3(2) . . . . ?
C12 B1 C13 C14 176.72(14) . . . . ?
C18 C13 C14 C15 0.7(2) . . . . ?
B1 C13 C14 C15 179.47(15) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 F1 179.34(14) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
F1 C16 C17 C18 -179.38(15) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C14 C13 C18 C17 -0.7(2) . . . . ?
B1 C13 C18 C17 -179.56(15) . . . . ?
N1' C1' C2' C3' 179(2) . . . . ?
C10' C1' C2' C3' -0.02(15) . . . . ?
C1' C2' C3' C4' -179.99(15) . . . . ?
C1' C2' C3' C8' 0.00(15) . . . . ?
C2' C3' C4' C5' 180.0(2) . . . . ?
C8' C3' C4' C5' 0.0(4) . . . . ?
C3' C4' C5' C6' 0.0(5) . . . . ?
C4' C5' C6' C7' 0.0(5) . . . . ?
C5' C6' C7' C8' 0.0(5) . . . . ?
C6' C7' C8' C9' -180.0(3) . . . . ?
C6' C7' C8' C3' 0.0(5) . . . . ?
C2' C3' C8' C9' 0.0(3) . . . . ?
C4' C3' C8' C9' 180.0(3) . . . . ?
C2' C3' C8' C7' 180.0(2) . . . . ?
C4' C3' C8' C7' 0.0(4) . . . . ?
C7' C8' C9' C10' -180.0(3) . . . . ?
C3' C8' C9' C10' 0.1(5) . . . . ?
C8' C9' C10' C1' -0.1(5) . . . . ?
C8' C9' C10' C11' 180.0(3) . . . . ?
C2' C1' C10' C9' 0.1(3) . . . . ?
N1' C1' C10' C9' -179.1(19) . . . . ?
C2' C1' C10' C11' 180.0(2) . . . . ?
N1' C1' C10' C11' 0.8(19) . . . . ?
C9' C10' C11' C12' 180.0(3) . . . . ?
C1' C10' C11' C12' 0.0(5) . . . . ?
C10' C11' C12' B1' 0.0(5) . . . . ?
C11' C12' B1' N1' -0.8(19) . . . . ?
C11' C12' B1' C13' -164(2) . . . . ?
C2' C1' N1' B1' 179(2) . . . . ?
C10' C1' N1' B1' -2(4) . . . . ?
C12' B1' N1' C1' 2(4) . . . . ?
C13' B1' N1' C1' 166(3) . . . . ?
N1' B1' C13' C18' -164(4) . . . . ?
C12' B1' C13' C18' -1(5) . . . . ?
N1' B1' C13' C14' 16(5) . . . . ?
C12' B1' C13' C14' 178(4) . . . . ?
C18' C13' C14' C15' -2(8) . . . . ?
B1' C13' C14' C15' 178(5) . . . . ?
C13' C14' C15' C16' -2(9) . . . . ?
C14' C15' C16' F1' -178(5) . . . . ?
C14' C15' C16' C17' 12(8) . . . . ?
F1' C16' C17' C18' 173(5) . . . . ?
C15' C16' C17' C18' -17(8) . . . . ?
C16' C17' C18' C13' 12(8) . . . . ?
C14' C13' C18' C17' -3(7) . . . . ?
B1' C13' C18' C17' 176(4) . . . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_1f
_database_code_depnum_ccdc_archive 'CCDC 1435444'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 B F3 N'
_chemical_formula_sum            'C19 H13 B F3 N'
_chemical_formula_weight         323.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.54619(13)
_cell_length_b                   5.86945(11)
_cell_length_c                   32.5219(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.2129(15)
_cell_angle_gamma                90
_cell_volume                     1436.57(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    5517
_cell_measurement_theta_min      5.42
_cell_measurement_theta_max      71.95

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.954
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            9494
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         5.455
_diffrn_reflns_theta_max         71.879
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2815
_reflns_number_gt                2523
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0566P)²+0.5830P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2815
_refine_ls_number_parameters     249
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.48816(16) 0.0609(2) 0.27574(4) 0.0150(3) Uani 1 1 d . . . . .
H1 H 0.385(2) -0.123(3) 0.2325(5) 0.027(4) Uiso 1 1 d . . . . .
C2 C 0.46930(16) -0.0918(2) 0.30738(4) 0.0159(3) Uani 1 1 d . . . . .
H2 H 0.4070 -0.2304 0.3019 0.019 Uiso 1 1 calc R U . . .
C3 C 0.54110(16) -0.0455(2) 0.34786(4) 0.0164(3) Uani 1 1 d . . . . .
C4 C 0.52680(17) -0.2026(2) 0.38082(4) 0.0183(3) Uani 1 1 d . . . . .
H4 H 0.4654 -0.3424 0.3759 0.022 Uiso 1 1 calc R U . . .
C5 C 0.60070(18) -0.1539(2) 0.41952(4) 0.0210(3) Uani 1 1 d . . . . .
H5 H 0.5902 -0.2604 0.4412 0.025 Uiso 1 1 calc R U . . .
C6 C 0.69281(18) 0.0537(2) 0.42760(4) 0.0218(3) Uani 1 1 d . . . . .
H6 H 0.7443 0.0850 0.4545 0.026 Uiso 1 1 calc R U . . .
C7 C 0.70770(17) 0.2089(2) 0.39677(4) 0.0198(3) Uani 1 1 d . . . . .
H7 H 0.7691 0.3479 0.4025 0.024 Uiso 1 1 calc R U . . .
C8 C 0.63213(16) 0.1648(2) 0.35610(4) 0.0168(3) Uani 1 1 d . . . . .
C9 C 0.64371(16) 0.3213(2) 0.32379(4) 0.0169(3) Uani 1 1 d . . . . .
H9 H 0.7008 0.4634 0.3294 0.020 Uiso 1 1 calc R U . . .
C10 C 0.57439(16) 0.2751(2) 0.28401(4) 0.0155(3) Uani 1 1 d . . . . .
C11 C 0.59439(16) 0.4344(2) 0.25075(4) 0.0165(3) Uani 1 1 d . . . . .
H11 H 0.6463 0.5789 0.2570 0.020 Uiso 1 1 calc R U . . .
C12 C 0.54196(17) 0.3851(2) 0.21110(4) 0.0179(3) Uani 1 1 d . . . . .
H12 H 0.5572 0.4936 0.1900 0.022 Uiso 1 1 calc R U . . .
C13 C 0.40686(16) 0.0683(2) 0.15513(4) 0.0168(3) Uani 1 1 d . . . . .
C14 C 0.32029(17) -0.1391(2) 0.14585(4) 0.0176(3) Uani 1 1 d . . . . .
H14 H 0.2895 -0.2350 0.1678 0.021 Uiso 1 1 calc R U . . .
C15 C 0.27863(17) -0.2075(2) 0.10543(4) 0.0192(3) Uani 1 1 d . . . . .
H15 H 0.2198 -0.3484 0.0998 0.023 Uiso 1 1 calc R U . . .
C16 C 0.32368(17) -0.0683(2) 0.07319(4) 0.0191(3) Uani 1 1 d . . . . .
C17 C 0.40972(18) 0.1371(2) 0.08112(4) 0.0206(3) Uani 1 1 d . . . . .
H17 H 0.4401 0.2318 0.0590 0.025 Uiso 1 1 calc R U . . .
C18 C 0.45128(17) 0.2035(2) 0.12172(4) 0.0193(3) Uani 1 1 d . . . . .
H18 H 0.5113 0.3439 0.1270 0.023 Uiso 1 1 calc R U . . .
B1 B 0.45741(18) 0.1518(2) 0.20048(4) 0.0166(3) Uani 1 1 d . . . . .
N1 N 0.43067(14) 0.01046(19) 0.23483(3) 0.0161(2) Uani 1 1 d . . . . .
C19 C 0.27910(19) -0.1469(3) 0.02974(4) 0.0242(3) Uani 0.917(6) 1 d D U P A 1
F1 F 0.1147(2) -0.2274(5) 0.02394(4) 0.0541(7) Uani 0.917(6) 1 d D U P A 1
F2 F 0.3874(3) -0.3139(4) 0.01883(5) 0.0460(5) Uani 0.917(6) 1 d D U P A 1
F3 F 0.2939(3) 0.0174(2) 0.00164(4) 0.0377(5) Uani 0.917(6) 1 d D U P A 1
C19' C 0.27910(19) -0.1469(3) 0.02974(4) 0.0242(3) Uani 0.083(6) 1 d D U P A 2
F1' F 0.180(3) -0.333(3) 0.0291(5) 0.050(4) Uani 0.083(6) 1 d D U P A 2
F2' F 0.4233(18) -0.211(4) 0.0131(5) 0.043(4) Uani 0.083(6) 1 d D U P A 2
F3' F 0.202(3) 0.013(2) 0.0075(4) 0.034(4) Uani 0.083(6) 1 d D U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3799(18) . ?
C1 N1 1.4005(16) . ?
C1 C10 1.4320(17) . ?
C2 C3 1.4126(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.4240(18) . ?
C3 C8 1.4282(18) . ?
C4 C5 1.3688(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.418(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.365(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.4251(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.4034(18) . ?
C9 C10 1.3863(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.4461(17) . ?
C11 C12 1.3519(18) . ?
C11 H11 0.9500 . ?
C12 B1 1.5394(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.4043(18) . ?
C13 C18 1.4057(18) . ?
C13 B1 1.5742(18) . ?
C14 C15 1.3882(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3910(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.3845(19) . ?
C16 C19 1.5010(18) . ?
C17 C18 1.3903(19) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
B1 N1 1.4175(18) . ?
N1 H1 0.86(2) . ?
C19 F1 1.3280(19) . ?
C19 F3 1.3389(18) . ?
C19 F2 1.341(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
C2 C1 N1 121.96(12) . . ?
C2 C1 C10 120.04(11) . . ?
N1 C1 C10 117.95(11) . . ?
C1 C2 C3 121.08(12) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 122.12(12) . . ?
C2 C3 C8 119.18(12) . . ?
C4 C3 C8 118.69(11) . . ?
C5 C4 C3 120.58(12) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.72(12) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.21(12) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.75(12) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 122.22(12) . . ?
C9 C8 C3 118.73(11) . . ?
C7 C8 C3 119.05(12) . . ?
C10 C9 C8 122.05(12) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C1 118.83(12) . . ?
C9 C10 C11 121.25(12) . . ?
C1 C10 C11 119.88(11) . . ?
C12 C11 C10 122.40(12) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 B1 119.46(12) . . ?
C11 C12 H12 120.3 . . ?
B1 C12 H12 120.3 . . ?
C14 C13 C18 117.19(11) . . ?
C14 C13 B1 123.23(11) . . ?
C18 C13 B1 119.57(12) . . ?
C15 C14 C13 121.58(12) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 119.54(12) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.55(12) . . ?
C17 C16 C19 120.83(12) . . ?
C15 C16 C19 118.62(12) . . ?
C16 C17 C18 119.41(12) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C13 121.73(12) . . ?
C17 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
N1 B1 C12 115.12(11) . . ?
N1 B1 C13 121.17(12) . . ?
C12 B1 C13 123.70(12) . . ?
C1 N1 B1 124.95(11) . . ?
C1 N1 H1 111.7(12) . . ?
B1 N1 H1 123.1(12) . . ?
F1 C19 F3 106.46(14) . . ?
F1 C19 F2 106.48(16) . . ?
F3 C19 F2 105.25(13) . . ?
F1 C19 C16 112.67(12) . . ?
F3 C19 C16 113.39(13) . . ?
F2 C19 C16 112.02(13) . . ?

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
N1 C1 C2 C3 174.75(11) . . . . ?
C10 C1 C2 C3 -2.95(18) . . . . ?
C1 C2 C3 C4 -178.58(12) . . . . ?
C1 C2 C3 C8 1.00(18) . . . . ?
C2 C3 C4 C5 178.83(12) . . . . ?
C8 C3 C4 C5 -0.75(19) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C9 179.46(12) . . . . ?
C6 C7 C8 C3 -0.40(19) . . . . ?
C2 C3 C8 C9 1.46(18) . . . . ?
C4 C3 C8 C9 -178.95(11) . . . . ?
C2 C3 C8 C7 -178.68(11) . . . . ?
C4 C3 C8 C7 0.92(18) . . . . ?
C7 C8 C9 C10 178.15(12) . . . . ?
C3 C8 C9 C10 -2.00(18) . . . . ?
C8 C9 C10 C1 0.09(18) . . . . ?
C8 C9 C10 C11 -177.28(12) . . . . ?
C2 C1 C10 C9 2.41(18) . . . . ?
N1 C1 C10 C9 -175.38(11) . . . . ?
C2 C1 C10 C11 179.81(11) . . . . ?
N1 C1 C10 C11 2.02(17) . . . . ?
C9 C10 C11 C12 174.05(12) . . . . ?
C1 C10 C11 C12 -3.28(19) . . . . ?
C10 C11 C12 B1 0.09(19) . . . . ?
C18 C13 C14 C15 -0.58(19) . . . . ?
B1 C13 C14 C15 -179.67(12) . . . . ?
C13 C14 C15 C16 0.16(19) . . . . ?
C14 C15 C16 C17 0.09(19) . . . . ?
C14 C15 C16 C19 179.34(12) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C19 C16 C17 C18 -179.13(12) . . . . ?
C16 C17 C18 C13 -0.6(2) . . . . ?
C14 C13 C18 C17 0.79(19) . . . . ?
B1 C13 C18 C17 179.91(12) . . . . ?
C11 C12 B1 N1 4.09(18) . . . . ?
C11 C12 B1 C13 -174.52(12) . . . . ?
C14 C13 B1 N1 5.34(19) . . . . ?
C18 C13 B1 N1 -173.73(11) . . . . ?
C14 C13 B1 C12 -176.13(12) . . . . ?
C18 C13 B1 C12 4.79(19) . . . . ?
C2 C1 N1 B1 -175.13(12) . . . . ?
C10 C1 N1 B1 2.62(18) . . . . ?
C12 B1 N1 C1 -5.55(18) . . . . ?
C13 B1 N1 C1 173.10(11) . . . . ?
C17 C16 C19 F1 -134.9(2) . . . . ?
C15 C16 C19 F1 45.9(2) . . . . ?
C17 C16 C19 F3 -13.9(2) . . . . ?
C15 C16 C19 F3 166.89(16) . . . . ?
C17 C16 C19 F2 105.09(19) . . . . ?
C15 C16 C19 F2 -74.2(2) . . . . ?

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_1g
_database_code_depnum_ccdc_archive 'CCDC 1435445'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 B N'
_chemical_formula_sum            'C21 H20 B N'
_chemical_formula_weight         297.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   7.44538(9)
_cell_length_b                   7.11221(8)
_cell_length_c                   15.95865(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.8062(11)
_cell_angle_gamma                90
_cell_volume                     842.089(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    7110
_cell_measurement_theta_min      5.55
_cell_measurement_theta_max      72.08

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.502
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            8578
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.564
_diffrn_reflns_theta_max         71.861
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3204
_reflns_number_gt                3130
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0518P)²+0.0800P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.2(5)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3204
_refine_ls_number_parameters     216
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0805
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3568(2) 0.5021(2) 0.89739(9) 0.0193(3) Uani 1 1 d . . . . .
C2 C 0.3855(2) 0.5644(2) 0.97974(9) 0.0207(3) Uani 1 1 d . . . . .
H2 H 0.4665 0.6654 0.9927 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2964(2) 0.4801(2) 1.04449(9) 0.0194(3) Uani 1 1 d . . . . .
C4 C 0.3230(2) 0.5413(2) 1.12994(9) 0.0220(3) Uani 1 1 d . . . . .
H4 H 0.4035 0.6420 1.1443 0.026 Uiso 1 1 calc R U . . .
C5 C 0.2338(2) 0.4565(2) 1.19119(9) 0.0234(3) Uani 1 1 d . . . . .
H5 H 0.2537 0.4984 1.2477 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1117(2) 0.3065(2) 1.17123(9) 0.0240(3) Uani 1 1 d . . . . .
H6 H 0.0496 0.2497 1.2143 0.029 Uiso 1 1 calc R U . . .
C7 C 0.0834(2) 0.2438(2) 1.09040(10) 0.0227(3) Uani 1 1 d . . . . .
H7 H 0.0019 0.1431 1.0777 0.027 Uiso 1 1 calc R U . . .
C8 C 0.17456(18) 0.3277(2) 1.02483(9) 0.0191(3) Uani 1 1 d . . . . .
C9 C 0.14836(19) 0.2656(2) 0.94105(9) 0.0198(3) Uani 1 1 d . . . . .
H9 H 0.0686 0.1637 0.9278 0.024 Uiso 1 1 calc R U . . .
C10 C 0.23541(19) 0.3488(2) 0.87722(9) 0.0186(3) Uani 1 1 d . . . . .
C11 C 0.2058(2) 0.2848(2) 0.79147(9) 0.0228(3) Uani 1 1 d . . . . .
H11 H 0.1253 0.1830 0.7791 0.027 Uiso 1 1 calc R U . . .
C12 C 0.2882(2) 0.3640(2) 0.72807(9) 0.0262(3) Uani 1 1 d . . . . .
H12 H 0.2672 0.3167 0.6724 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5156(2) 0.6438(2) 0.67855(9) 0.0211(3) Uani 1 1 d . . . . .
C14 C 0.4393(2) 0.8094(2) 0.64267(9) 0.0238(3) Uani 1 1 d . . . . .
C15 C 0.5327(2) 0.9134(2) 0.58618(10) 0.0265(3) Uani 1 1 d . . . . .
H15 H 0.4800 1.0248 0.5622 0.032 Uiso 1 1 calc R U . . .
C16 C 0.7012(2) 0.8573(2) 0.56440(9) 0.0260(3) Uani 1 1 d . . . . .
C17 C 0.7717(2) 0.6890(2) 0.59689(9) 0.0252(3) Uani 1 1 d . . . . .
H17 H 0.8844 0.6460 0.5805 0.030 Uiso 1 1 calc R U . . .
C18 C 0.6808(2) 0.5817(2) 0.65301(9) 0.0230(3) Uani 1 1 d . . . . .
C19 C 0.2559(2) 0.8721(3) 0.66502(12) 0.0342(4) Uani 1 1 d . . . . .
H19A H 0.2137 0.9763 0.6283 0.051 Uiso 1 1 calc R U . . .
H19B H 0.2637 0.9138 0.7237 0.051 Uiso 1 1 calc R U . . .
H19C H 0.1710 0.7669 0.6576 0.051 Uiso 1 1 calc R U . . .
C20 C 0.8067(3) 0.9773(3) 0.50786(11) 0.0370(4) Uani 1 1 d . . . . .
H20A H 0.8957 0.8993 0.4822 0.055 Uiso 1 1 calc R U . . .
H20B H 0.8687 1.0776 0.5410 0.055 Uiso 1 1 calc R U . . .
H20C H 0.7242 1.0331 0.4636 0.055 Uiso 1 1 calc R U . . .
C21 C 0.7608(2) 0.3986(3) 0.68634(11) 0.0318(4) Uani 1 1 d . . . . .
H21A H 0.8770 0.3776 0.6632 0.048 Uiso 1 1 calc R U . . .
H21B H 0.6786 0.2950 0.6696 0.048 Uiso 1 1 calc R U . . .
H21C H 0.7786 0.4043 0.7478 0.048 Uiso 1 1 calc R U . . .
B1 B 0.4162(2) 0.5313(3) 0.74647(11) 0.0224(4) Uani 1 1 d . . . . .
N1 N 0.44115(17) 0.58568(19) 0.83213(8) 0.0219(3) Uani 1 1 d . . . . .
H1 H 0.516(3) 0.682(3) 0.8478(14) 0.036(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
C1 C2 1.386(2) . ?
C1 N1 1.3934(19) . ?
C1 C10 1.436(2) . ?
C2 C3 1.408(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.429(2) . ?
C3 C8 1.431(2) . ?
C4 C5 1.367(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.420(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.364(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.425(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.406(2) . ?
C9 C10 1.385(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.442(2) . ?
C11 C12 1.349(2) . ?
C11 H11 0.9500 . ?
C12 B1 1.537(2) . ?
C12 H12 0.9500 . ?
C13 C18 1.399(2) . ?
C13 C14 1.408(2) . ?
C13 B1 1.580(2) . ?
C14 C15 1.396(2) . ?
C14 C19 1.507(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(2) . ?
C16 C20 1.509(2) . ?
C17 C18 1.394(2) . ?
C17 H17 0.9500 . ?
C18 C21 1.510(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
B1 N1 1.418(2) . ?
N1 H1 0.91(3) . ?

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
C2 C1 N1 121.94(13) . . ?
C2 C1 C10 119.95(13) . . ?
N1 C1 C10 118.11(13) . . ?
C1 C2 C3 121.02(14) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 122.32(14) . . ?
C2 C3 C8 119.37(13) . . ?
C4 C3 C8 118.31(13) . . ?
C5 C4 C3 120.75(15) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.72(14) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.18(14) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.82(14) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 122.03(13) . . ?
C9 C8 C3 118.75(13) . . ?
C7 C8 C3 119.21(13) . . ?
C10 C9 C8 121.96(13) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C1 118.95(13) . . ?
C9 C10 C11 121.31(14) . . ?
C1 C10 C11 119.74(13) . . ?
C12 C11 C10 122.47(14) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 B1 119.56(13) . . ?
C11 C12 H12 120.2 . . ?
B1 C12 H12 120.2 . . ?
C18 C13 C14 118.69(14) . . ?
C18 C13 B1 120.87(14) . . ?
C14 C13 B1 120.44(14) . . ?
C15 C14 C13 120.00(14) . . ?
C15 C14 C19 120.41(15) . . ?
C13 C14 C19 119.59(14) . . ?
C16 C15 C14 121.27(14) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 118.36(14) . . ?
C15 C16 C20 120.91(15) . . ?
C17 C16 C20 120.72(15) . . ?
C16 C17 C18 121.48(14) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C13 120.03(14) . . ?
C17 C18 C21 119.97(14) . . ?
C13 C18 C21 120.00(14) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 B1 C12 115.11(14) . . ?
N1 B1 C13 119.47(14) . . ?
C12 B1 C13 125.41(13) . . ?
C1 N1 B1 124.98(14) . . ?
C1 N1 H1 115.0(13) . . ?
B1 N1 H1 120.0(14) . . ?

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
N1 C1 C2 C3 178.82(13) . . . . ?
C10 C1 C2 C3 -0.3(2) . . . . ?
C1 C2 C3 C4 -179.93(14) . . . . ?
C1 C2 C3 C8 0.1(2) . . . . ?
C2 C3 C4 C5 179.83(13) . . . . ?
C8 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C9 179.83(14) . . . . ?
C6 C7 C8 C3 -0.3(2) . . . . ?
C2 C3 C8 C9 0.40(19) . . . . ?
C4 C3 C8 C9 -179.60(15) . . . . ?
C2 C3 C8 C7 -179.45(15) . . . . ?
C4 C3 C8 C7 0.56(19) . . . . ?
C7 C8 C9 C10 179.20(13) . . . . ?
C3 C8 C9 C10 -0.6(2) . . . . ?
C8 C9 C10 C1 0.4(2) . . . . ?
C8 C9 C10 C11 -179.39(13) . . . . ?
C2 C1 C10 C9 0.1(2) . . . . ?
N1 C1 C10 C9 -179.09(13) . . . . ?
C2 C1 C10 C11 179.89(14) . . . . ?
N1 C1 C10 C11 0.7(2) . . . . ?
C9 C10 C11 C12 179.64(14) . . . . ?
C1 C10 C11 C12 -0.2(2) . . . . ?
C10 C11 C12 B1 -1.1(3) . . . . ?
C18 C13 C14 C15 -3.4(2) . . . . ?
B1 C13 C14 C15 176.48(14) . . . . ?
C18 C13 C14 C19 176.06(14) . . . . ?
B1 C13 C14 C19 -4.1(2) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C19 C14 C15 C16 -179.59(15) . . . . ?
C14 C15 C16 C17 3.3(2) . . . . ?
C14 C15 C16 C20 -175.87(14) . . . . ?
C15 C16 C17 C18 -2.9(2) . . . . ?
C20 C16 C17 C18 176.28(14) . . . . ?
C16 C17 C18 C13 -0.7(2) . . . . ?
C16 C17 C18 C21 179.42(14) . . . . ?
C14 C13 C18 C17 3.8(2) . . . . ?
B1 C13 C18 C17 -176.08(14) . . . . ?
C14 C13 C18 C21 -176.31(14) . . . . ?
B1 C13 C18 C21 3.8(2) . . . . ?
C11 C12 B1 N1 1.8(2) . . . . ?
C11 C12 B1 C13 -177.24(15) . . . . ?
C18 C13 B1 N1 95.16(18) . . . . ?
C14 C13 B1 N1 -84.68(19) . . . . ?
C18 C13 B1 C12 -85.8(2) . . . . ?
C14 C13 B1 C12 94.35(19) . . . . ?
C2 C1 N1 B1 -179.04(15) . . . . ?
C10 C1 N1 B1 0.1(2) . . . . ?
C12 B1 N1 C1 -1.3(2) . . . . ?
C13 B1 N1 C1 177.79(13) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.030

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_8a
_database_code_depnum_ccdc_archive 'CCDC 1435446'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.5423(2)
_cell_length_b                   5.9013(2)
_cell_length_c                   28.5913(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.099(3)
_cell_angle_gamma                90
_cell_volume                     1269.33(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4139
_cell_measurement_theta_min      6.17
_cell_measurement_theta_max      71.70

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.569
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            8823
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.099
_diffrn_reflns_theta_max         71.889
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2491
_reflns_number_gt                2298
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0433P)²+1.3779P]
 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_number_reflns         2491
_refine_ls_number_parameters     362
_refine_ls_number_restraints     829
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1518
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9876(6) 0.4418(5) 0.28051(11) 0.0207(6) Uani 0.873(2) 1 d D U P A 1
C2 C 0.9654(3) 0.5927(4) 0.31718(8) 0.0214(5) Uani 0.873(2) 1 d D U P A 1
H2 H 0.9037 0.7309 0.3109 0.026 Uiso 0.873(2) 1 calc R U P A 1
C3 C 1.0318(3) 0.5452(5) 0.36298(9) 0.0214(5) Uani 0.873(2) 1 d D U P A 1
C4 C 1.0118(3) 0.6998(4) 0.40090(12) 0.0241(5) Uani 0.873(2) 1 d D U P A 1
H4 H 0.9508 0.8390 0.3951 0.029 Uiso 0.873(2) 1 calc R U P A 1
C5 C 1.0793(4) 0.6494(5) 0.44507(11) 0.0265(6) Uani 0.873(2) 1 d D U P A 1
H5 H 1.0642 0.7532 0.4699 0.032 Uiso 0.873(2) 1 calc R U P A 1
C6 C 1.1723(4) 0.4430(7) 0.45444(10) 0.0285(6) Uani 0.873(2) 1 d D U P A 1
H6 H 1.2196 0.4104 0.4854 0.034 Uiso 0.873(2) 1 calc R U P A 1
C7 C 1.1939(3) 0.2912(5) 0.41926(13) 0.0266(6) Uani 0.873(2) 1 d D U P A 1
H7 H 1.2565 0.1540 0.4260 0.032 Uiso 0.873(2) 1 calc R U P A 1
C8 C 1.1237(4) 0.3364(5) 0.37260(10) 0.0221(5) Uani 0.873(2) 1 d D U P A 1
C9 C 1.1414(3) 0.1814(4) 0.33624(8) 0.0230(5) Uani 0.873(2) 1 d D U P A 1
H9 H 1.1995 0.0409 0.3427 0.028 Uiso 0.873(2) 1 calc R U P A 1
C10 C 1.0750(3) 0.2299(5) 0.29056(9) 0.0214(5) Uani 0.873(2) 1 d D U P A 1
C11 C 1.0947(18) 0.0777(13) 0.25270(14) 0.0228(9) Uani 0.873(2) 1 d D U P A 1
H11 H 1.1441 -0.0682 0.2589 0.027 Uiso 0.873(2) 1 calc R U P A 1
C12 C 1.0440(3) 0.1373(4) 0.20763(9) 0.0225(5) Uani 0.873(2) 1 d D U P A 1
H12 H 1.0622 0.0332 0.1831 0.027 Uiso 0.873(2) 1 calc R U P A 1
C13 C 0.9636(3) 0.3539(4) 0.19616(8) 0.0209(5) Uani 0.873(2) 1 d D U P A 1
C14 C 0.9338(4) 0.4965(4) 0.23302(10) 0.0212(6) Uani 0.873(2) 1 d D U P A 1
H14 H 0.8751 0.6366 0.2265 0.025 Uiso 0.873(2) 1 calc R U P A 1
C15 C 0.9223(3) 0.4184(5) 0.14619(8) 0.0217(5) Uani 0.873(2) 1 d D U P A 1
C16 C 0.9741(3) 0.2817(4) 0.10951(12) 0.0258(5) Uani 0.873(2) 1 d D U P A 1
H16 H 1.0365 0.1449 0.1167 0.031 Uiso 0.873(2) 1 calc R U P A 1
C17 C 0.9364(4) 0.3413(6) 0.06286(11) 0.0290(6) Uani 0.873(2) 1 d D U P A 1
H17 H 0.9720 0.2447 0.0387 0.035 Uiso 0.873(2) 1 calc R U P A 1
C18 C 0.8469(4) 0.5418(6) 0.05150(9) 0.0280(6) Uani 0.873(2) 1 d D U P A 1
H18 H 0.8206 0.5825 0.0196 0.034 Uiso 0.873(2) 1 calc R U P A 1
C19 C 0.7964(3) 0.6820(5) 0.08708(13) 0.0268(6) Uani 0.873(2) 1 d D U P A 1
H19 H 0.7366 0.8203 0.0796 0.032 Uiso 0.873(2) 1 calc R U P A 1
C20 C 0.8329(3) 0.6208(5) 0.13386(10) 0.0246(5) Uani 0.873(2) 1 d D U P A 1
H20 H 0.7966 0.7180 0.1579 0.030 Uiso 0.873(2) 1 calc R U P A 1
C1' C 0.949(4) 0.434(3) 0.2272(6) 0.022(2) Uani 0.127(2) 1 d D U P A 2
C2' C 0.8841(19) 0.587(2) 0.1938(4) 0.023(2) Uani 0.127(2) 1 d D U P A 2
H2' H 0.8382 0.7286 0.2031 0.028 Uiso 0.127(2) 1 calc R U P A 2
C3' C 0.886(2) 0.534(3) 0.1463(5) 0.023(2) Uani 0.127(2) 1 d D U P A 2
C4' C 0.819(2) 0.691(3) 0.1113(7) 0.023(2) Uani 0.127(2) 1 d D U P A 2
H4' H 0.7709 0.8309 0.1207 0.028 Uiso 0.127(2) 1 calc R U P A 2
C5' C 0.822(3) 0.645(4) 0.0649(7) 0.027(2) Uani 0.127(2) 1 d D U P A 2
H5' H 0.7796 0.7525 0.0421 0.033 Uiso 0.127(2) 1 calc R U P A 2
C6' C 0.890(3) 0.433(4) 0.0511(6) 0.027(2) Uani 0.127(2) 1 d D U P A 2
H6' H 0.8884 0.3956 0.0188 0.032 Uiso 0.127(2) 1 calc R U P A 2
C7' C 0.958(3) 0.283(3) 0.0837(7) 0.027(2) Uani 0.127(2) 1 d D U P A 2
H7' H 1.0082 0.1457 0.0735 0.032 Uiso 0.127(2) 1 calc R U P A 2
C8' C 0.956(2) 0.325(3) 0.1323(6) 0.023(2) Uani 0.127(2) 1 d D U P A 2
C9' C 1.024(2) 0.170(2) 0.1659(4) 0.025(2) Uani 0.127(2) 1 d D U P A 2
H9' H 1.0715 0.0298 0.1565 0.030 Uiso 0.127(2) 1 calc R U P A 2
C10' C 1.020(3) 0.223(3) 0.2130(5) 0.022(2) Uani 0.127(2) 1 d D U P A 2
C11' C 1.101(13) 0.081(9) 0.2486(8) 0.023(3) Uani 0.127(2) 1 d D U P A 2
H11' H 1.1552 -0.0565 0.2396 0.027 Uiso 0.127(2) 1 calc R U P A 2
C12' C 1.105(2) 0.134(3) 0.2952(6) 0.025(2) Uani 0.127(2) 1 d D U P A 2
H12' H 1.1471 0.0252 0.3179 0.030 Uiso 0.127(2) 1 calc R U P A 2
C13' C 1.046(2) 0.353(3) 0.3103(5) 0.0251(18) Uani 0.127(2) 1 d D U P A 2
C14' C 0.967(5) 0.487(4) 0.2756(7) 0.023(2) Uani 0.127(2) 1 d D U P A 2
H14' H 0.9206 0.6283 0.2849 0.028 Uiso 0.127(2) 1 calc R U P A 2
C15' C 1.076(2) 0.424(3) 0.3608(5) 0.022(2) Uani 0.127(2) 1 d D U P A 2
C16' C 1.178(2) 0.295(3) 0.3921(7) 0.023(2) Uani 0.127(2) 1 d D U P A 2
H16' H 1.2336 0.1625 0.3811 0.027 Uiso 0.127(2) 1 calc R U P A 2
C17' C 1.202(3) 0.349(4) 0.4389(7) 0.025(3) Uani 0.127(2) 1 d D U P A 2
H17' H 1.2661 0.2496 0.4601 0.030 Uiso 0.127(2) 1 calc R U P A 2
C18' C 1.133(3) 0.548(4) 0.4550(6) 0.025(2) Uani 0.127(2) 1 d D U P A 2
H18' H 1.1581 0.5936 0.4866 0.030 Uiso 0.127(2) 1 calc R U P A 2
C19' C 1.029(3) 0.680(3) 0.4247(8) 0.024(2) Uani 0.127(2) 1 d D U P A 2
H19' H 0.9731 0.8117 0.4359 0.029 Uiso 0.127(2) 1 calc R U P A 2
C20' C 1.003(2) 0.621(3) 0.3778(7) 0.021(2) Uani 0.127(2) 1 d D U P A 2
H20' H 0.9350 0.7174 0.3569 0.025 Uiso 0.127(2) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.395(4) . ?
C1 C14 1.426(3) . ?
C1 C10 1.433(4) . ?
C2 C3 1.397(3) . ?
C2 H2 0.9500 . ?
C3 C8 1.431(4) . ?
C3 C4 1.433(4) . ?
C4 C5 1.360(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.421(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.365(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.425(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.398(3) . ?
C9 C10 1.394(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.423(5) . ?
C11 C12 1.364(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.443(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(3) . ?
C13 C15 1.490(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.400(4) . ?
C15 C20 1.404(4) . ?
C16 C17 1.389(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C1' C2' 1.378(16) . ?
C1' C14' 1.418(17) . ?
C1' C10' 1.425(16) . ?
C2' C3' 1.395(15) . ?
C2' H2' 0.9500 . ?
C3' C8' 1.409(16) . ?
C3' C4' 1.428(16) . ?
C4' C5' 1.355(16) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.418(17) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.357(17) . ?
C6' H6' 0.9500 . ?
C7' C8' 1.413(16) . ?
C7' H7' 0.9500 . ?
C8' C9' 1.397(15) . ?
C9' C10' 1.385(15) . ?
C9' H9' 0.9500 . ?
C10' C11' 1.425(19) . ?
C11' C12' 1.37(2) . ?
C11' H11' 0.9500 . ?
C12' C13' 1.444(15) . ?
C12' H12' 0.9500 . ?
C13' C14' 1.370(16) . ?
C13' C15' 1.506(15) . ?
C14' H14' 0.9500 . ?
C15' C16' 1.368(16) . ?
C15' C20' 1.390(16) . ?
C16' C17' 1.376(17) . ?
C16' H16' 0.9500 . ?
C17' C18' 1.375(17) . ?
C17' H17' 0.9500 . ?
C18' C19' 1.372(17) . ?
C18' H18' 0.9500 . ?
C19' C20' 1.384(17) . ?
C19' H19' 0.9500 . ?
C20' H20' 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
C2 C1 C14 122.0(2) . . ?
C2 C1 C10 119.0(2) . . ?
C14 C1 C10 118.9(3) . . ?
C1 C2 C3 121.5(2) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C8 119.3(3) . . ?
C2 C3 C4 122.1(3) . . ?
C8 C3 C4 118.6(2) . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 C3 119.4(3) . . ?
C7 C8 C3 118.9(2) . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 122.2(3) . . ?
C9 C10 C1 119.7(2) . . ?
C11 C10 C1 118.0(3) . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 121.9(3) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 117.1(2) . . ?
C14 C13 C15 122.8(2) . . ?
C12 C13 C15 120.0(2) . . ?
C13 C14 C1 122.6(3) . . ?
C13 C14 H14 118.7 . . ?
C1 C14 H14 118.7 . . ?
C16 C15 C20 117.2(2) . . ?
C16 C15 C13 121.4(3) . . ?
C20 C15 C13 121.5(3) . . ?
C17 C16 C15 121.6(2) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 119.4(2) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 121.3(2) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
C2' C1' C14' 122.5(15) . . ?
C2' C1' C10' 119.8(15) . . ?
C14' C1' C10' 117.3(15) . . ?
C1' C2' C3' 120.0(14) . . ?
C1' C2' H2' 120.0 . . ?
C3' C2' H2' 120.0 . . ?
C2' C3' C8' 120.1(15) . . ?
C2' C3' C4' 120.7(16) . . ?
C8' C3' C4' 119.2(13) . . ?
C5' C4' C3' 121.7(15) . . ?
C5' C4' H4' 119.1 . . ?
C3' C4' H4' 119.1 . . ?
C4' C5' C6' 118.7(16) . . ?
C4' C5' H5' 120.6 . . ?
C6' C5' H5' 120.6 . . ?
C7' C6' C5' 120.6(16) . . ?
C7' C6' H6' 119.7 . . ?
C5' C6' H6' 119.7 . . ?
C6' C7' C8' 122.0(16) . . ?
C6' C7' H7' 119.0 . . ?
C8' C7' H7' 119.0 . . ?
C9' C8' C3' 120.3(16) . . ?
C9' C8' C7' 122.1(16) . . ?
C3' C8' C7' 117.7(13) . . ?
C10' C9' C8' 119.3(14) . . ?
C10' C9' H9' 120.4 . . ?
C8' C9' H9' 120.4 . . ?
C9' C10' C1' 120.6(14) . . ?
C9' C10' C11' 121.6(15) . . ?
C1' C10' C11' 117.6(15) . . ?
C12' C11' C10' 122.7(19) . . ?
C12' C11' H11' 118.7 . . ?
C10' C11' H11' 118.7 . . ?
C11' C12' C13' 120.7(17) . . ?
C11' C12' H12' 119.7 . . ?
C13' C12' H12' 119.7 . . ?
C14' C13' C12' 115.4(14) . . ?
C14' C13' C15' 124.1(15) . . ?
C12' C13' C15' 120.4(13) . . ?
C13' C14' C1' 125.8(19) . . ?
C13' C14' H14' 117.1 . . ?
C1' C14' H14' 117.1 . . ?
C16' C15' C20' 117.1(13) . . ?
C16' C15' C13' 120.8(17) . . ?
C20' C15' C13' 122.1(17) . . ?
C15' C16' C17' 122.4(15) . . ?
C15' C16' H16' 118.8 . . ?
C17' C16' H16' 118.8 . . ?
C18' C17' C16' 119.8(16) . . ?
C18' C17' H17' 120.1 . . ?
C16' C17' H17' 120.1 . . ?
C19' C18' C17' 119.2(15) . . ?
C19' C18' H18' 120.4 . . ?
C17' C18' H18' 120.4 . . ?
C18' C19' C20' 120.1(15) . . ?
C18' C19' H19' 119.9 . . ?
C20' C19' H19' 119.9 . . ?
C19' C20' C15' 121.2(14) . . ?
C19' C20' H20' 119.4 . . ?
C15' C20' H20' 119.4 . . ?

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
C14 C1 C2 C3 -174.6(3) . . . . ?
C10 C1 C2 C3 2.3(5) . . . . ?
C1 C2 C3 C8 -0.4(4) . . . . ?
C1 C2 C3 C4 179.3(3) . . . . ?
C2 C3 C4 C5 -179.5(2) . . . . ?
C8 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 -178.7(2) . . . . ?
C6 C7 C8 C3 0.8(4) . . . . ?
C2 C3 C8 C9 -1.6(3) . . . . ?
C4 C3 C8 C9 178.7(2) . . . . ?
C2 C3 C8 C7 178.9(2) . . . . ?
C4 C3 C8 C7 -0.8(3) . . . . ?
C7 C8 C9 C10 -178.7(2) . . . . ?
C3 C8 C9 C10 1.7(3) . . . . ?
C8 C9 C10 C11 178.5(7) . . . . ?
C8 C9 C10 C1 0.1(4) . . . . ?
C2 C1 C10 C9 -2.1(5) . . . . ?
C14 C1 C10 C9 174.8(3) . . . . ?
C2 C1 C10 C11 179.4(7) . . . . ?
C14 C1 C10 C11 -3.6(8) . . . . ?
C9 C10 C11 C12 -173.7(7) . . . . ?
C1 C10 C11 C12 4.7(14) . . . . ?
C10 C11 C12 C13 -1.8(15) . . . . ?
C11 C12 C13 C14 -2.3(8) . . . . ?
C11 C12 C13 C15 175.6(8) . . . . ?
C12 C13 C14 C1 3.4(5) . . . . ?
C15 C13 C14 C1 -174.5(3) . . . . ?
C2 C1 C14 C13 176.4(3) . . . . ?
C10 C1 C14 C13 -0.5(6) . . . . ?
C14 C13 C15 C16 172.0(3) . . . . ?
C12 C13 C15 C16 -5.8(3) . . . . ?
C14 C13 C15 C20 -6.7(4) . . . . ?
C12 C13 C15 C20 175.5(2) . . . . ?
C20 C15 C16 C17 -1.0(4) . . . . ?
C13 C15 C16 C17 -179.8(2) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C17 C18 C19 C20 -0.9(4) . . . . ?
C18 C19 C20 C15 0.5(4) . . . . ?
C16 C15 C20 C19 0.4(3) . . . . ?
C13 C15 C20 C19 179.2(2) . . . . ?
C14' C1' C2' C3' 173(3) . . . . ?
C10' C1' C2' C3' 1(3) . . . . ?
C1' C2' C3' C8' -1(3) . . . . ?
C1' C2' C3' C4' 180.0(19) . . . . ?
C2' C3' C4' C5' 178.8(17) . . . . ?
C8' C3' C4' C5' -1(3) . . . . ?
C3' C4' C5' C6' 1(3) . . . . ?
C4' C5' C6' C7' -3(3) . . . . ?
C5' C6' C7' C8' 3(3) . . . . ?
C2' C3' C8' C9' 0(3) . . . . ?
C4' C3' C8' C9' 179.3(16) . . . . ?
C2' C3' C8' C7' -178.5(16) . . . . ?
C4' C3' C8' C7' 1(3) . . . . ?
C6' C7' C8' C9' 179.3(18) . . . . ?
C6' C7' C8' C3' -2(3) . . . . ?
C3' C8' C9' C10' 1(3) . . . . ?
C7' C8' C9' C10' 178.9(18) . . . . ?
C8' C9' C10' C1' 0(3) . . . . ?
C8' C9' C10' C11' -174(5) . . . . ?
C2' C1' C10' C9' 0(3) . . . . ?
C14' C1' C10' C9' -173(3) . . . . ?
C2' C1' C10' C11' 174(5) . . . . ?
C14' C1' C10' C11' 1(6) . . . . ?
C9' C10' C11' C12' 178(6) . . . . ?
C1' C10' C11' C12' 3(11) . . . . ?
C10' C11' C12' C13' -8(11) . . . . ?
C11' C12' C13' C14' 8(6) . . . . ?
C11' C12' C13' C15' -171(5) . . . . ?
C12' C13' C14' C1' -4(5) . . . . ?
C15' C13' C14' C1' 175(3) . . . . ?
C2' C1' C14' C13' -173(3) . . . . ?
C10' C1' C14' C13' 0(5) . . . . ?
C14' C13' C15' C16' -171(3) . . . . ?
C12' C13' C15' C16' 8(3) . . . . ?
C14' C13' C15' C20' 9(3) . . . . ?
C12' C13' C15' C20' -172.1(17) . . . . ?
C20' C15' C16' C17' 3(3) . . . . ?
C13' C15' C16' C17' -177.3(17) . . . . ?
C15' C16' C17' C18' -5(3) . . . . ?
C16' C17' C18' C19' 6(3) . . . . ?
C17' C18' C19' C20' -5(3) . . . . ?
C18' C19' C20' C15' 3(3) . . . . ?
C16' C15' C20' C19' -2(3) . . . . ?
C13' C15' C20' C19' 178.3(17) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-2



