# 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_1g
_database_code_depnum_ccdc_archive 'CCDC 1453177'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 B N2'
_chemical_formula_sum            'C19 H13 B N2'
_chemical_formula_weight         280.12

_twin_information                
;
 * * * CRYSALIS TWIN DATA REDUCTION FINALIZING (Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)) * * *
Laue class: 2/m (b-unique) - 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 (   7.464    5.898   32.110    90.02    91.96    90.00)
Matrix 2 is taken from component 2 (   7.465    5.898   32.110    90.01    92.01    89.98)
Twin analysis: Component 1 with component 2
TL  =UB[1]-1*UB[2]:  -0.9999  -0.0008   0.0003     0.0007  -1.0001   0.0001     0.3045   0.0068   1.0000   det 1.000062
TL-1=UB[2]*UB[1]-1:  -1.0000   0.0008   0.0003    -0.0007  -0.9999   0.0001     0.3045   0.0065   0.9999   det 0.999938
Rot= 179.9474 deg around the following vectors: 
Reciprocal space (hkl): 0.0003 0.0001 1.0000
Direct space (uvw)    : 0.1505 0.0033 0.9886
 
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:  -4.2139  -1.8798   1.6894  d=   0.1974
  2:  -0.1330   0.4268  20.7119  d=   0.0382
  3:   4.2073   1.8990  -0.7440  d=   0.2297
  4:   0.3765  -0.3168 -20.7511  d=   0.0389
  5:   2.6154  -3.1765   2.5821  d=   0.2397
  6:   4.2444  -0.0121   9.4217  d=   0.1417
  7:  -4.2583   0.2268  -9.2342  d=   0.1291
  8:  -3.0055  -2.9993  -9.0661  d=   0.2184
  9:   3.0055   2.9993   9.0661  d=   0.2349
 10:   3.9970  -0.0040  -9.2178  d=   0.1298
 11:  -1.0054   0.9984 -18.7018  d=   0.1342
 12:  -2.9956   3.0031   5.8931  d=   0.2184
 13:  -5.0015   0.0029  -4.4774  d=   0.1246
 14:  -4.9989   0.0040   3.5224  d=   0.1198
DC PROFFITRRPTWIN ALL INFO: Component 2
DC PROFFITRRPTWIN INFO: Face list of component 2 
  1:   4.2129   1.8828   0.3939  d=   0.1974
  2:   0.1402  -0.4241  20.6726  d=   0.0382
  3:  -4.2059  -1.9019   0.5495  d=   0.2297
  4:  -0.3837   0.3139 -20.6369  d=   0.0389
  5:  -2.6171   3.1747   3.3576  d=   0.2397
  6:  -4.2412   0.0103  10.7133  d=   0.1417
  7:   4.2553  -0.2250 -10.5286  d=   0.1291
  8:   3.0000   3.0000 -10.0000  d=   0.2184
  9:  -3.0000  -3.0000  10.0000  d=   0.2349
 10:  -4.0000   0.0000  -8.0000  d=   0.1298
 11:   1.0000  -1.0000 -19.0000  d=   0.1342
 12:   3.0000  -3.0000   5.0000  d=   0.2184
 13:   5.0000   0.0000  -6.0000  d=   0.1246
 14:   5.0000   0.0000   2.0000  d=   0.1198
 
DC PROFFITRRPTWIN INFO: Step 4 - Analysing composite reflections of 2 components
 
Component 1: 9139 observations read
Component 2: 9133 observations read

10482 composite observations collected (2776 fully isolated, 7706 overlapped), 18 skipped due to one or more missing parts and 33 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  |       2207 |    21.1 <--- ALMOST SEPARATED
   0.20 - 0.40  |       1170 |    11.2
   0.40 - 0.60  |       1707 |    16.3
   0.60 - 0.80  |       1755 |    16.7
   0.80 - 1.00  |        867 |     8.3 <--- FULLY OVERLAPPED
 -------------- | ---------- | ------------ 
      Total     |       7706 |    73.5

 
DC PROFFITRRPTWIN INFO: Step 5 - Scaling data & analysing twin ratios of 2 components
 
Computed twin ratios:
Twin 1: 82.22% (5582 common observations, 1804 merged)
Twin 2: 17.78% (4313 common observations, 1804 merged)

Preparing data for SCALE3 ABSPACK...

SCALING COMPONENT 1

4822 of 9096 reflections used for ABSPACK refinement
PROFFIT INFO: Inet (after scale3 abspack): min=-11974323.0000 max=88384560.0000
PROFFIT INFO: sig(Inet) (after scale3 abspack): min=647.3510 max=156989.4531
PROFFIT INFO: 53 observations on 'bad frames' rejected


SCALING COMPONENT 2

4830 of 9090 reflections used for ABSPACK refinement
PROFFIT INFO: Inet (after scale3 abspack): min=-16535955.0000 max=88384560.0000
PROFFIT INFO: sig(Inet) (after scale3 abspack): min=468.2157 max=156989.4531
PROFFIT INFO: 107 observations on 'bad frames' rejected

Computed twin ratios:
Twin 1: 82.53% (5532 common observations, 1789 merged)
Twin 2: 17.47% (4266 common observations, 1789 merged)

DC PROFFITRRPTWIN INFO: Determining HKLF4 overlap threshold for completeness requirement (>=80.0%)
DC PROFFITRRPTWIN INFO: New HKLF4 overlap threshold - 0.55

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: P2/m (b-unique)
                      #        #        #      average    mean      mean        
         intensity measured   kept    unique  redundancy   F2     F2/sig(F2)   Rint   Rsigma
#--------------------------------------------------------------------------------------------
 88384560- 1759029      731      731      246    3.0   5453604.08   139.92    0.035    0.043
  1743837-  766993      649      649      246    2.6   1213538.71    65.72    0.062    0.066
   766718-  421928      632      632      246    2.6    589142.44    42.75    0.070    0.075
   421882-  236205      649      649      246    2.6    320670.69    31.10    0.078    0.084
   235543-  133707      589      589      246    2.4    180993.63    22.22    0.095    0.102
   133704-   71782      590      590      246    2.4    100937.11    15.37    0.099    0.108
    71031-   29776      611      611      246    2.5     48872.75     8.67    0.196    0.196
    29615-   11045      613      613      246    2.5     19653.11     4.23    0.285    0.299
    11011-    2521      542      542      246    2.2      5729.37     1.46    0.487    0.528
     2447- -126650      463      463      251    1.8     -3384.32    -0.43    0.970    1.348
#------------------------------------------------------------------------------------------
 88384560- -126650     6069     6069     2465    2.5    916828.08    36.71    0.047    0.055
 

Statistics vs resolution - point group symmetry: P2/m (b-unique)
resolu-      #        #        #               average    mean      mean          
tion(A)   measured   kept    unique           redundancy   F2     F2/sig(F2)   Rint   Rsigma   RsigmaA
#------------------------------------------------------------------------------------------------------
 inf-1.79      705      705      246             2.9   2580972.93    95.85    0.027    0.035     0.006
1.79-1.40      605      605      246             2.5   1426164.15    48.61    0.041    0.045     0.011
1.40-1.22      760      760      246             3.1   1085868.47    34.23    0.050    0.066     0.015
1.22-1.11      714      714      246             2.9    951511.73    31.32    0.068    0.076     0.017
1.11-1.02      613      613      246             2.5    729414.71    27.21    0.067    0.074     0.019
1.02-0.96      544      544      246             2.2    485529.53    23.56    0.056    0.062     0.024
0.96-0.91      604      604      246             2.5    383002.01    22.11    0.075    0.076     0.026
0.91-0.87      562      562      246             2.3    297776.40    19.62    0.059    0.065     0.028
0.87-0.84      452      452      246             1.8    292237.11    23.63    0.065    0.067     0.026
0.84-0.81      510      510      251             2.0    264982.32    25.24    0.056    0.059     0.023
#------------------------------------------------------------------------------------------------------
 inf-0.81     6069     6069     2465             2.5    916828.08    36.71    0.047    0.055     0.014
 

Statistics vs resolution (taking redundancy into account) - point group symmetry: P2/m (b-unique)
resolu-      #        #        #       %       average    mean      mean          
tion(A)    kept     theory   unique complete  redundancy   F2     F2/sig(F2)   Rint  RsigmaB
#--------------------------------------------------------------------------------------------
 inf-1.79      705      318      246   77.4      2.9   2580972.93   181.06    0.027    0.003
1.79-1.40      605      314      246   78.3      2.5   1426164.15    85.61    0.041    0.007
1.40-1.22      760      304      246   80.9      3.1   1085868.47    68.76    0.050    0.008
1.22-1.11      714      306      246   80.4      2.9    951511.73    59.70    0.068    0.010
1.11-1.02      613      330      246   74.5      2.5    729414.71    47.89    0.067    0.012
1.02-0.96      544      315      246   78.1      2.2    485529.53    39.60    0.056    0.015
0.96-0.91      604      308      246   79.9      2.5    383002.01    38.46    0.075    0.016
0.91-0.87      562      292      246   84.2      2.3    297776.40    32.44    0.059    0.018
0.87-0.84      452      287      246   85.7      1.8    292237.11    34.86    0.065    0.016
0.84-0.81      510      300      251   83.7      2.0    264982.32    38.59    0.056    0.015
#--------------------------------------------------------------------------------------------
 inf-0.81     6069     3080     2465   80.0      2.5    916828.08    66.26    0.047    0.009
DC PROFFITRRPTWIN INFO: Step 7 - Generating output files
 
HKLF 4
Reflections read=9041, from those 6069 with overlapping factor < 0.547 written to file D:\Data\xs0821a\twin_twin1_hklf4.hkl, 2972 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           9041      7449      3715     2.01     33.35     0.018     0.018

RINT ANALYSIS FOR OVERLAPPED REFLECTIONS
 Components measured    kept     unique redundancy F2/sig(F2) Rint      Rsigma
#------------------------------------------------------------------------------
1,2           7564      6054      2824     2.14     33.07     0.019     0.019

RINT ANALYSIS FOR ISOLATED REFLECTIONS
 Component measured     kept     unique redundancy F2/sig(F2) Rint      Rsigma
#------------------------------------------------------------------------------
     1        1477      1395       891     1.57     30.86     0.017     0.016
     2           0         0         0     0.00      0.00     0.000     0.000

3715 merged reflections saved into file: D:\Data\xs0821a\twin_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 0.17467 
;

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           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                   7.46841(17)
_cell_length_b                   5.90109(11)
_cell_length_c                   32.1078(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.971(3)
_cell_angle_gamma                90
_cell_volume                     1414.21(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    3977
_cell_measurement_theta_min      6.13
_cell_measurement_theta_max      72.01

_exptl_crystal_description       tabular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.595
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_T_max  0.955
_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_absorpt_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            7449
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0184
_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       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         5.514
_diffrn_reflns_theta_max         71.887
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3487
_reflns_number_gt                3146
_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 1.171.37.35 (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-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_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)+(0.0833P)²+0.7948P] 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         3487
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1526
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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 0.0142(2) 0.1496(3) 0.72206(5) 0.0142(4) Uani 1 1 d . . . . .
C2 C 0.0384(2) -0.0031(3) 0.69022(5) 0.0150(4) Uani 1 1 d . . . . .
H2 H 0.0975 -0.1427 0.6961 0.018 Uiso 1 1 calc R U . . .
C3 C -0.0234(2) 0.0446(3) 0.64905(5) 0.0150(4) Uani 1 1 d . . . . .
C4 C -0.0024(2) -0.1117(3) 0.61582(5) 0.0174(4) Uani 1 1 d . . . . .
H4 H 0.0557 -0.2525 0.6211 0.021 Uiso 1 1 calc R U . . .
C5 C -0.0648(3) -0.0618(3) 0.57633(6) 0.0215(4) Uani 1 1 d . . . . .
H5 H -0.0505 -0.1683 0.5545 0.026 Uiso 1 1 calc R U . . .
C6 C -0.1505(3) 0.1480(3) 0.56780(6) 0.0225(4) Uani 1 1 d . . . . .
H6 H -0.1925 0.1815 0.5402 0.027 Uiso 1 1 calc R U . . .
C7 C -0.1733(2) 0.3026(3) 0.59883(6) 0.0197(4) Uani 1 1 d . . . . .
H7 H -0.2314 0.4424 0.5927 0.024 Uiso 1 1 calc R U . . .
C8 C -0.1107(2) 0.2557(3) 0.64039(5) 0.0158(4) Uani 1 1 d . . . . .
C9 C -0.1296(2) 0.4109(3) 0.67302(5) 0.0160(4) Uani 1 1 d . . . . .
H9 H -0.1853 0.5527 0.6672 0.019 Uiso 1 1 calc R U . . .
C10 C -0.0697(2) 0.3641(3) 0.71347(5) 0.0146(4) Uani 1 1 d . . . . .
C11 C -0.0955(2) 0.5217(3) 0.74717(5) 0.0161(4) Uani 1 1 d . . . . .
H11 H -0.1460 0.6660 0.7408 0.019 Uiso 1 1 calc R U . . .
C12 C -0.0511(2) 0.4729(3) 0.78716(5) 0.0169(4) Uani 1 1 d . . . . .
H12 H -0.0707 0.5808 0.8085 0.020 Uiso 1 1 calc R U . . .
C13 C 0.0745(2) 0.1559(3) 0.84382(5) 0.0158(4) Uani 1 1 d . . . . .
C14 C 0.1590(2) -0.0519(3) 0.85277(5) 0.0175(4) Uani 1 1 d . . . . .
H14 H 0.1928 -0.1463 0.8304 0.021 Uiso 1 1 calc R U . . .
C15 C 0.1941(2) -0.1227(3) 0.89331(6) 0.0187(4) Uani 1 1 d . . . . .
H15 H 0.2515 -0.2640 0.8987 0.022 Uiso 1 1 calc R U . . .
C16 C 0.1446(2) 0.0155(3) 0.92632(5) 0.0187(4) Uani 1 1 d . . . . .
C17 C 0.0594(2) 0.2219(3) 0.91863(6) 0.0207(4) Uani 1 1 d . . . . .
H17 H 0.0253 0.3152 0.9411 0.025 Uiso 1 1 calc R U . . .
C18 C 0.0250(2) 0.2897(3) 0.87782(5) 0.0185(4) Uani 1 1 d . . . . .
H18 H -0.0336 0.4303 0.8727 0.022 Uiso 1 1 calc R U . . .
C19 C 0.1842(3) -0.0590(4) 0.96842(6) 0.0259(4) Uani 1 1 d . . . . .
N1 N 0.06415(19) 0.0991(3) 0.76329(4) 0.0156(3) Uani 1 1 d . . . . .
H1 H 0.1198 -0.0302 0.7681 0.019 Uiso 1 1 calc R U . . .
N2 N 0.2180(3) -0.1198(4) 1.00167(5) 0.0390(5) Uani 1 1 d . . . . .
B1 B 0.0319(2) 0.2403(3) 0.79803(6) 0.0163(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(2) . ?
C1 N1 1.395(2) . ?
C1 C10 1.435(2) . ?
C2 C3 1.414(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.423(2) . ?
C3 C8 1.429(2) . ?
C4 C5 1.368(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.416(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.366(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.426(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.402(2) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.445(2) . ?
C11 C12 1.346(2) . ?
C11 H11 0.9500 . ?
C12 B1 1.541(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.404(2) . ?
C13 C18 1.407(2) . ?
C13 B1 1.574(3) . ?
C14 C15 1.384(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(3) . ?
C16 C19 1.443(2) . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 N2 1.146(3) . ?
N1 B1 1.419(2) . ?
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 121.74(16) . . ?
C2 C1 C10 120.09(15) . . ?
N1 C1 C10 118.14(15) . . ?
C1 C2 C3 121.08(16) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 122.10(16) . . ?
C2 C3 C8 119.19(16) . . ?
C4 C3 C8 118.72(16) . . ?
C5 C4 C3 120.83(17) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.33(17) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.64(17) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.53(17) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 122.29(16) . . ?
C9 C8 C3 118.76(15) . . ?
C7 C8 C3 118.95(16) . . ?
C10 C9 C8 122.13(16) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C1 118.72(16) . . ?
C9 C10 C11 121.72(16) . . ?
C1 C10 C11 119.52(15) . . ?
C12 C11 C10 122.78(16) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C11 C12 B1 119.39(16) . . ?
C11 C12 H12 120.3 . . ?
B1 C12 H12 120.3 . . ?
C14 C13 C18 117.33(16) . . ?
C14 C13 B1 122.84(16) . . ?
C18 C13 B1 119.82(16) . . ?
C15 C14 C13 121.73(17) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 119.37(17) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.50(16) . . ?
C17 C16 C19 120.73(17) . . ?
C15 C16 C19 118.77(17) . . ?
C18 C17 C16 119.28(17) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C13 121.79(17) . . ?
C17 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
N2 C19 C16 179.0(2) . . ?
C1 N1 B1 124.97(15) . . ?
C1 N1 H1 117.5 . . ?
B1 N1 H1 117.5 . . ?
N1 B1 C12 115.00(16) . . ?
N1 B1 C13 120.92(17) . . ?
C12 B1 C13 124.05(16) . . ?

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 175.86(15) . . . . ?
C10 C1 C2 C3 -2.0(2) . . . . ?
C1 C2 C3 C4 -179.04(16) . . . . ?
C1 C2 C3 C8 0.6(2) . . . . ?
C2 C3 C4 C5 179.48(16) . . . . ?
C8 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 179.24(17) . . . . ?
C6 C7 C8 C3 0.1(3) . . . . ?
C2 C3 C8 C9 1.1(2) . . . . ?
C4 C3 C8 C9 -179.28(15) . . . . ?
C2 C3 C8 C7 -179.77(15) . . . . ?
C4 C3 C8 C7 -0.1(2) . . . . ?
C7 C8 C9 C10 179.54(16) . . . . ?
C3 C8 C9 C10 -1.3(2) . . . . ?
C8 C9 C10 C1 -0.1(2) . . . . ?
C8 C9 C10 C11 -177.76(15) . . . . ?
C2 C1 C10 C9 1.7(2) . . . . ?
N1 C1 C10 C9 -176.20(15) . . . . ?
C2 C1 C10 C11 179.50(15) . . . . ?
N1 C1 C10 C11 1.6(2) . . . . ?
C9 C10 C11 C12 174.71(16) . . . . ?
C1 C10 C11 C12 -3.0(3) . . . . ?
C10 C11 C12 B1 0.3(3) . . . . ?
C18 C13 C14 C15 -0.6(3) . . . . ?
B1 C13 C14 C15 -179.67(16) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C14 C15 C16 C19 -179.17(17) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C19 C16 C17 C18 179.29(18) . . . . ?
C16 C17 C18 C13 -0.3(3) . . . . ?
C14 C13 C18 C17 0.7(3) . . . . ?
B1 C13 C18 C17 179.83(16) . . . . ?
C2 C1 N1 B1 -175.24(16) . . . . ?
C10 C1 N1 B1 2.7(2) . . . . ?
C1 N1 B1 C12 -5.1(2) . . . . ?
C1 N1 B1 C13 173.19(14) . . . . ?
C11 C12 B1 N1 3.5(2) . . . . ?
C11 C12 B1 C13 -174.73(16) . . . . ?
C14 C13 B1 N1 5.4(3) . . . . ?
C18 C13 B1 N1 -173.68(16) . . . . ?
C14 C13 B1 C12 -176.50(16) . . . . ?
C18 C13 B1 C12 4.4(3) . . . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_1h
_database_code_depnum_ccdc_archive 'CCDC 1453178'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 B N2 O2'
_chemical_formula_sum            'C18 H13 B N2 O2'
_chemical_formula_weight         300.11

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'
O O 0.0492 0.0322 '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                   7.35557(13)
_cell_length_b                   5.95525(11)
_cell_length_c                   31.4266(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.5796(17)
_cell_angle_gamma                90
_cell_volume                     1376.55(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    5535
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      72.02

_exptl_crystal_description       'small rod'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.762
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_T_max  0.940
_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_absorpt_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            8815
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.812
_diffrn_reflns_theta_max         71.886
_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             2703
_reflns_number_gt                2390
_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-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_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)+(0.0642P)²+0.5256P] 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         2703
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.98313(15) 0.4163(2) 0.27823(4) 0.0097(3) Uani 1 1 d . . . . .
C2 C 0.95822(15) 0.5681(2) 0.31086(4) 0.0106(3) Uani 1 1 d . . . . .
H2 H 0.8991 0.7068 0.3051 0.013 Uiso 1 1 calc R U . . .
C3 C 1.01908(16) 0.52092(19) 0.35267(4) 0.0105(3) Uani 1 1 d . . . . .
C4 C 0.99860(16) 0.6769(2) 0.38665(4) 0.0123(3) Uani 1 1 d . . . . .
H4 H 0.9415 0.8174 0.3814 0.015 Uiso 1 1 calc R U . . .
C5 C 1.06037(17) 0.6262(2) 0.42674(4) 0.0155(3) Uani 1 1 d . . . . .
H5 H 1.0461 0.7323 0.4490 0.019 Uiso 1 1 calc R U . . .
C6 C 1.14552(18) 0.4170(2) 0.43537(4) 0.0169(3) Uani 1 1 d . . . . .
H6 H 1.1876 0.3838 0.4633 0.020 Uiso 1 1 calc R U . . .
C7 C 1.16719(17) 0.2630(2) 0.40354(4) 0.0140(3) Uani 1 1 d . . . . .
H7 H 1.2240 0.1232 0.4096 0.017 Uiso 1 1 calc R U . . .
C8 C 1.10539(16) 0.3100(2) 0.36132(4) 0.0111(3) Uani 1 1 d . . . . .
C9 C 1.12463(16) 0.1558(2) 0.32793(4) 0.0112(3) Uani 1 1 d . . . . .
H9 H 1.1795 0.0144 0.3336 0.013 Uiso 1 1 calc R U . . .
C10 C 1.06592(15) 0.2036(2) 0.28678(4) 0.0100(3) Uani 1 1 d . . . . .
C11 C 1.09392(15) 0.04611(19) 0.25240(4) 0.0110(3) Uani 1 1 d . . . . .
H11 H 1.1434 -0.0974 0.2588 0.013 Uiso 1 1 calc R U . . .
C12 C 1.05200(16) 0.0962(2) 0.21144(4) 0.0121(3) Uani 1 1 d . . . . .
H12 H 1.0730 -0.0104 0.1895 0.014 Uiso 1 1 calc R U . . .
C13 C 0.92958(15) 0.4098(2) 0.15390(4) 0.0110(3) Uani 1 1 d . . . . .
C14 C 0.85129(16) 0.6199(2) 0.14484(4) 0.0119(3) Uani 1 1 d . . . . .
H14 H 0.8202 0.7163 0.1677 0.014 Uiso 1 1 calc R U . . .
C15 C 0.81814(16) 0.6905(2) 0.10350(4) 0.0124(3) Uani 1 1 d . . . . .
H15 H 0.7683 0.8347 0.0978 0.015 Uiso 1 1 calc R U . . .
C16 C 0.85987(16) 0.5443(2) 0.07065(4) 0.0122(3) Uani 1 1 d . . . . .
C17 C 0.93679(17) 0.3348(2) 0.07742(4) 0.0138(3) Uani 1 1 d . . . . .
H17 H 0.9636 0.2379 0.0543 0.017 Uiso 1 1 calc R U . . .
C18 C 0.97333(17) 0.2716(2) 0.11918(4) 0.0130(3) Uani 1 1 d . . . . .
H18 H 1.0296 0.1306 0.1245 0.016 Uiso 1 1 calc R U . . .
B1 B 0.97010(18) 0.3269(2) 0.20067(4) 0.0110(3) Uani 1 1 d . . . . .
N1 N 0.93542(13) 0.46755(17) 0.23619(3) 0.0111(2) Uani 1 1 d . . . . .
H1 H 0.8799 0.5961 0.2314 0.013 Uiso 1 1 calc R U . . .
N2 N 0.81914(15) 0.61724(18) 0.02689(3) 0.0165(3) Uani 1 1 d . . . . .
O1 O 0.81051(16) 0.81930(17) 0.01988(3) 0.0293(3) Uani 1 1 d . . . . .
O2 O 0.79606(14) 0.47163(17) -0.00033(3) 0.0240(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3807(16) . ?
C1 N1 1.3971(15) . ?
C1 C10 1.4301(16) . ?
C2 C3 1.4119(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.4246(16) . ?
C3 C8 1.4322(16) . ?
C4 C5 1.3686(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4196(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.3676(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4260(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4026(17) . ?
C9 C10 1.3885(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.4469(16) . ?
C11 C12 1.3539(16) . ?
C11 H11 0.9500 . ?
C12 B1 1.5366(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.4054(16) . ?
C13 C18 1.4069(16) . ?
C13 B1 1.5759(18) . ?
C14 C15 1.3848(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3870(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3854(17) . ?
C16 N2 1.4700(15) . ?
C17 C18 1.3888(17) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
B1 N1 1.4207(16) . ?
N1 H1 0.8800 . ?
N2 O1 1.2248(15) . ?
N2 O2 1.2288(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 121.70(11) . . ?
C2 C1 C10 119.99(11) . . ?
N1 C1 C10 118.27(10) . . ?
C1 C2 C3 121.18(11) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 122.21(11) . . ?
C2 C3 C8 119.14(11) . . ?
C4 C3 C8 118.65(11) . . ?
C5 C4 C3 120.66(11) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.72(11) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.24(11) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.69(11) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 122.27(11) . . ?
C9 C8 C3 118.68(11) . . ?
C7 C8 C3 119.05(11) . . ?
C10 C9 C8 122.00(11) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C1 118.97(11) . . ?
C9 C10 C11 121.16(11) . . ?
C1 C10 C11 119.82(10) . . ?
C12 C11 C10 122.30(11) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 B1 119.44(11) . . ?
C11 C12 H12 120.3 . . ?
B1 C12 H12 120.3 . . ?
C14 C13 C18 117.40(11) . . ?
C14 C13 B1 122.75(11) . . ?
C18 C13 B1 119.84(11) . . ?
C15 C14 C13 121.88(11) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 118.02(11) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C17 C16 C15 122.94(11) . . ?
C17 C16 N2 119.26(11) . . ?
C15 C16 N2 117.79(11) . . ?
C16 C17 C18 117.67(11) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 H17 121.2 . . ?
C17 C18 C13 122.04(11) . . ?
C17 C18 H18 119.0 . . ?
C13 C18 H18 119.0 . . ?
N1 B1 C12 115.28(11) . . ?
N1 B1 C13 120.97(11) . . ?
C12 B1 C13 123.74(11) . . ?
C1 N1 B1 124.68(10) . . ?
C1 N1 H1 117.7 . . ?
B1 N1 H1 117.7 . . ?
O1 N2 O2 124.15(11) . . ?
O1 N2 C16 117.92(10) . . ?
O2 N2 C16 117.93(11) . . ?

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 -175.31(10) . . . . ?
C10 C1 C2 C3 2.30(17) . . . . ?
C1 C2 C3 C4 178.56(11) . . . . ?
C1 C2 C3 C8 -1.05(17) . . . . ?
C2 C3 C4 C5 -179.53(11) . . . . ?
C8 C3 C4 C5 0.09(17) . . . . ?
C3 C4 C5 C6 -0.25(19) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C8 0.18(19) . . . . ?
C6 C7 C8 C9 -179.74(12) . . . . ?
C6 C7 C8 C3 -0.34(18) . . . . ?
C2 C3 C8 C9 -0.75(17) . . . . ?
C4 C3 C8 C9 179.62(10) . . . . ?
C2 C3 C8 C7 179.83(10) . . . . ?
C4 C3 C8 C7 0.20(17) . . . . ?
C7 C8 C9 C10 -179.30(11) . . . . ?
C3 C8 C9 C10 1.30(17) . . . . ?
C8 C9 C10 C1 -0.08(17) . . . . ?
C8 C9 C10 C11 177.36(11) . . . . ?
C2 C1 C10 C9 -1.73(17) . . . . ?
N1 C1 C10 C9 175.96(10) . . . . ?
C2 C1 C10 C11 -179.21(10) . . . . ?
N1 C1 C10 C11 -1.52(16) . . . . ?
C9 C10 C11 C12 -174.28(11) . . . . ?
C1 C10 C11 C12 3.13(17) . . . . ?
C10 C11 C12 B1 -0.58(18) . . . . ?
C18 C13 C14 C15 -0.14(18) . . . . ?
B1 C13 C14 C15 179.45(11) . . . . ?
C13 C14 C15 C16 1.79(18) . . . . ?
C14 C15 C16 C17 -1.62(18) . . . . ?
C14 C15 C16 N2 178.14(10) . . . . ?
C15 C16 C17 C18 -0.22(18) . . . . ?
N2 C16 C17 C18 -179.98(11) . . . . ?
C16 C17 C18 C13 1.98(18) . . . . ?
C14 C13 C18 C17 -1.81(18) . . . . ?
B1 C13 C18 C17 178.59(11) . . . . ?
C11 C12 B1 N1 -3.34(17) . . . . ?
C11 C12 B1 C13 175.35(11) . . . . ?
C14 C13 B1 N1 -2.65(18) . . . . ?
C18 C13 B1 N1 176.92(11) . . . . ?
C14 C13 B1 C12 178.72(11) . . . . ?
C18 C13 B1 C12 -1.70(18) . . . . ?
C2 C1 N1 B1 174.85(11) . . . . ?
C10 C1 N1 B1 -2.80(17) . . . . ?
C12 B1 N1 C1 5.13(17) . . . . ?
C13 B1 N1 C1 -173.60(10) . . . . ?
C17 C16 N2 O1 -155.92(12) . . . . ?
C15 C16 N2 O1 24.32(17) . . . . ?
C17 C16 N2 O2 24.02(17) . . . . ?
C15 C16 N2 O2 -155.75(12) . . . . ?

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.052

