# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_8a
_database_code_depnum_ccdc_archive 'CCDC 1475987'
_audit_update_record             
;
2016-04-22 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;
_audit_creation_date             2015-06-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        8a
_chemical_formula_moiety         'C16 H16 B N3 O2'
_chemical_formula_sum            'C16 H16 B N3 O2'
_chemical_formula_weight         293.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H14 B N3 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   25.8560(9)
_cell_length_b                   5.37038(17)
_cell_length_c                   21.5154(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.646(3)
_cell_angle_gamma                90
_cell_volume                     2926.05(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3234
_cell_measurement_temperature    99.98(11)
_cell_measurement_theta_max      29.2970
_cell_measurement_theta_min      3.3920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.2588
_exptl_crystal_size_mid          0.1815
_exptl_crystal_size_min          0.1003
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5839
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.753
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00   44.00   1.0000   26.5150
omega____ theta____ kappa____ phi______ frames
    -       10.3201  -99.0000  120.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   80.00   1.0000   26.5150
omega____ theta____ kappa____ phi______ frames
    -       10.3201   57.0000 -120.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0007332000
_diffrn_orient_matrix_UB_12      0.0099506000
_diffrn_orient_matrix_UB_13      0.0330406000
_diffrn_orient_matrix_UB_21      -0.0247474000
_diffrn_orient_matrix_UB_22      0.0618245000
_diffrn_orient_matrix_UB_23      -0.0064187000
_diffrn_orient_matrix_UB_31      -0.0130893000
_diffrn_orient_matrix_UB_32      -0.1163065000
_diffrn_orient_matrix_UB_33      -0.0005783000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2583
_reflns_number_total             2976
_reflns_odcompleteness_completeness 99.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+4.0600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1059
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.38303(7) 0.5355(3) 0.60787(8) 0.0193(4) Uani 1 1 d . . . . .
C1 C 0.40419(6) 0.3315(3) 0.66072(7) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.37506(6) 0.3155(3) 0.70919(7) 0.0216(3) Uani 1 1 d . . . . .
H2 H 0.3482 0.4306 0.7094 0.026 Uiso 1 1 calc R . . . .
C3 C 0.38441(6) 0.1372(3) 0.75652(7) 0.0229(4) Uani 1 1 d . . . . .
H3 H 0.3643 0.1340 0.7878 0.027 Uiso 1 1 calc R . . . .
C4 C 0.42402(6) -0.0366(3) 0.75675(7) 0.0232(4) Uani 1 1 d . . . . .
H4 H 0.4298 -0.1617 0.7873 0.028 Uiso 1 1 calc R . . . .
C5 C 0.45485(6) -0.0228(3) 0.71129(7) 0.0211(3) Uani 1 1 d . . . . .
H5 H 0.4821 -0.1369 0.7124 0.025 Uiso 1 1 calc R . . . .
C6 C 0.44605(6) 0.1585(3) 0.66358(7) 0.0168(3) Uani 1 1 d . . . . .
C7 C 0.48353(6) 0.1532(3) 0.61994(7) 0.0161(3) Uani 1 1 d . . . . .
C8 C 0.51547(6) -0.0389(3) 0.60827(7) 0.0178(3) Uani 1 1 d . . . . .
H8 H 0.5171 -0.1991 0.6250 0.021 Uiso 1 1 calc R . . . .
C9 C 0.58539(6) -0.0687(3) 0.54177(7) 0.0192(3) Uani 1 1 d . . . . .
H9A H 0.5897 0.0180 0.5036 0.023 Uiso 1 1 calc R . . . .
H9B H 0.5747 -0.2382 0.5301 0.023 Uiso 1 1 calc R . . . .
C10 C 0.63763(6) -0.0732(3) 0.58819(7) 0.0180(3) Uani 1 1 d . . . . .
C11 C 0.65173(6) 0.1119(3) 0.63332(8) 0.0223(4) Uani 1 1 d . . . . .
H11 H 0.6285 0.2422 0.6357 0.027 Uiso 1 1 calc R . . . .
C12 C 0.70032(7) 0.1040(3) 0.67503(8) 0.0273(4) Uani 1 1 d . . . . .
H12 H 0.7093 0.2276 0.7056 0.033 Uiso 1 1 calc R . . . .
C13 C 0.73535(7) -0.0870(4) 0.67126(8) 0.0279(4) Uani 1 1 d . . . . .
H13 H 0.7679 -0.0919 0.6992 0.034 Uiso 1 1 calc R . . . .
C14 C 0.72193(7) -0.2706(4) 0.62589(9) 0.0297(4) Uani 1 1 d . . . . .
H14 H 0.7457 -0.3981 0.6230 0.036 Uiso 1 1 calc R . . . .
C15 C 0.67308(7) -0.2654(3) 0.58462(8) 0.0243(4) Uani 1 1 d . . . . .
H15 H 0.6640 -0.3906 0.5545 0.029 Uiso 1 1 calc R . . . .
C16 C 0.31197(7) 0.8161(4) 0.56498(8) 0.0290(4) Uani 1 1 d . . . . .
H16A H 0.3137 0.7632 0.5228 0.043 Uiso 1 1 calc GR . . . .
H16B H 0.3317 0.9675 0.5747 0.043 Uiso 1 1 calc GR . . . .
H16C H 0.2758 0.8443 0.5676 0.043 Uiso 1 1 calc GR . . . .
N1 N 0.49493(5) 0.3528(2) 0.58594(6) 0.0183(3) Uani 1 1 d . . . . .
N2 N 0.53156(5) 0.2931(2) 0.55388(6) 0.0191(3) Uani 1 1 d . . . . .
N3 N 0.54379(5) 0.0537(2) 0.56770(6) 0.0166(3) Uani 1 1 d . . . . .
O1 O 0.40718(5) 0.6200(2) 0.56202(5) 0.0218(3) Uani 1 1 d . . . . .
H1 H 0.4411(10) 0.552(5) 0.5658(11) 0.054(7) Uiso 1 1 d . . . . .
O2 O 0.33393(4) 0.6271(2) 0.60940(5) 0.0247(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C1 1.594(2) . ?
B1 O1 1.348(2) . ?
B1 O2 1.368(2) . ?
C1 C2 1.407(2) . ?
C1 C6 1.418(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.400(2) . ?
C6 C7 1.480(2) . ?
C7 C8 1.376(2) . ?
C7 N1 1.363(2) . ?
C8 H8 0.9300 . ?
C8 N3 1.343(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.509(2) . ?
C9 N3 1.4638(19) . ?
C10 C11 1.386(2) . ?
C10 C15 1.393(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(2) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 O2 1.431(2) . ?
N1 N2 1.3189(18) . ?
N2 N3 1.3428(18) . ?
O1 H1 0.94(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
O1 B1 C1 127.62(15) . . ?
O1 B1 O2 117.75(15) . . ?
O2 B1 C1 114.61(14) . . ?
C2 C1 B1 114.37(14) . . ?
C2 C1 C6 116.49(14) . . ?
C6 C1 B1 129.06(14) . . ?
C1 C2 H2 118.4 . . ?
C3 C2 C1 123.21(15) . . ?
C3 C2 H2 118.4 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.24(15) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.53(15) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.62(15) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 125.23(14) . . ?
C5 C6 C1 119.81(14) . . ?
C5 C6 C7 114.95(14) . . ?
C8 C7 C6 128.62(14) . . ?
N1 C7 C6 124.46(14) . . ?
N1 C7 C8 106.81(13) . . ?
C7 C8 H8 127.3 . . ?
N3 C8 C7 105.48(14) . . ?
N3 C8 H8 127.3 . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
N3 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
N3 C9 C10 112.54(12) . . ?
C11 C10 C9 121.72(14) . . ?
C11 C10 C15 119.16(15) . . ?
C15 C10 C9 119.11(14) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.42(15) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.18(16) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.82(16) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.20(16) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.20(16) . . ?
C14 C15 H15 119.9 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
N2 N1 C7 110.19(13) . . ?
N1 N2 N3 106.19(12) . . ?
C8 N3 C9 128.37(13) . . ?
N2 N3 C8 111.32(13) . . ?
N2 N3 C9 120.23(13) . . ?
B1 O1 H1 111.6(14) . . ?
B1 O2 C16 118.96(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 N1 0.93 2.57 3.329(2) 138.5 1_545
C9 H9A O1 0.97 2.41 3.317(2) 154.8 5_666
O1 H1 N1 0.94(3) 1.74(3) 2.6458(17) 161(2) .

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
B1 C1 C2 C3 174.63(15) . . . . ?
B1 C1 C6 C5 -173.55(15) . . . . ?
B1 C1 C6 C7 7.6(2) . . . . ?
C1 B1 O2 C16 178.36(14) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C6 C7 C8 -161.18(15) . . . . ?
C1 C6 C7 N1 23.2(2) . . . . ?
C2 C1 C6 C5 2.9(2) . . . . ?
C2 C1 C6 C7 -175.91(14) . . . . ?
C2 C3 C4 C5 2.6(2) . . . . ?
C3 C4 C5 C6 -2.0(2) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C4 C5 C6 C7 178.08(14) . . . . ?
C5 C6 C7 C8 20.0(2) . . . . ?
C5 C6 C7 N1 -155.67(14) . . . . ?
C6 C1 C2 C3 -2.3(2) . . . . ?
C6 C7 C8 N3 -176.83(14) . . . . ?
C6 C7 N1 N2 176.96(13) . . . . ?
C7 C8 N3 C9 177.26(14) . . . . ?
C7 C8 N3 N2 0.48(16) . . . . ?
C7 N1 N2 N3 -0.22(16) . . . . ?
C8 C7 N1 N2 0.52(17) . . . . ?
C9 C10 C11 C12 -179.37(15) . . . . ?
C9 C10 C15 C14 178.54(15) . . . . ?
C10 C9 N3 C8 -78.73(19) . . . . ?
C10 C9 N3 N2 97.80(16) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C10 C15 C14 0.0(2) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C10 0.8(3) . . . . ?
C15 C10 C11 C12 -0.9(2) . . . . ?
N1 C7 C8 N3 -0.59(16) . . . . ?
N1 N2 N3 C8 -0.17(16) . . . . ?
N1 N2 N3 C9 -177.25(12) . . . . ?
N3 C9 C10 C11 -29.9(2) . . . . ?
N3 C9 C10 C15 151.58(14) . . . . ?
O1 B1 C1 C2 168.61(16) . . . . ?
O1 B1 C1 C6 -14.9(3) . . . . ?
O1 B1 O2 C16 -3.4(2) . . . . ?
O2 B1 C1 C2 -13.3(2) . . . . ?
O2 B1 C1 C6 163.20(15) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-34 0 -4 0.0880 -34.0001 0.0000 -4.0000 -0.1571 0.8671 0.4473
-18 6 -6 0.0667 -17.9998 6.0000 -6.0000 -0.1517 0.8549 -0.4588
34 1 4 0.0959 34.0001 1.0000 4.0000 0.1670 -0.8053 -0.5637
-6 -7 4 0.1203 -6.0002 -7.0000 4.0000 0.0581 -0.3100 0.8904
13 -7 6 0.0938 12.9998 -7.0000 6.0000 0.1381 -0.7930 0.6405
0 1 -30 0.0361 -0.0002 1.0000 -30.0000 -0.9813 0.2544 -0.0990
1 0 29 0.0596 1.0002 -0.0000 29.0000 0.9589 -0.2109 -0.0299
-4 -1 -29 0.0450 -4.0002 -1.0000 -29.0000 -0.9711 0.2233 0.1854
16 6 12 0.1217 16.0003 6.0000 12.0000 0.4679 -0.1020 -0.9142
-13 -6 19 0.1269 -13.0001 -6.0000 19.0000 0.5585 -0.1712 0.8570
32 -1 -18 0.0743 31.9999 -1.0000 -18.0000 -0.5812 -0.7382 -0.2921
12 -7 -13 0.0898 11.9997 -7.0000 -13.0000 -0.4904 -0.6463 0.6646
-6 7 10 0.0907 -5.9997 7.0000 10.0000 0.3957 0.5171 -0.7414
-28 4 18 0.0805 -27.9998 4.0000 18.0000 0.6140 0.8247 -0.1091
-34 -1 17 0.1119 -34.0000 -1.0000 17.0000 0.5268 0.6705 0.5515
9 -1 -30 0.0410 8.9998 -1.0000 -30.0000 -0.9946 -0.0920 0.0159

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

data_13a
_database_code_depnum_ccdc_archive 'CCDC 1475996'
_audit_update_record             
;
2016-04-22 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;
_audit_creation_date             2015-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        13a
_chemical_formula_moiety         'C24 H24 B N3 O4'
_chemical_formula_sum            'C24 H24 B N3 O4'
_chemical_formula_weight         429.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H24 B N3 O4'
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'

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

_cell_length_a                   7.1065(4)
_cell_length_b                   9.0913(6)
_cell_length_c                   17.6850(11)
_cell_angle_alpha                81.994(5)
_cell_angle_beta                 84.409(5)
_cell_angle_gamma                68.790(6)
_cell_volume                     1053.43(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3063
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      73.9350
_cell_measurement_theta_min      5.2120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.2165
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.0282
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6836
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.242
_diffrn_reflns_theta_min         5.058
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   13.00   1.0000    1.1400
omega____ theta____ kappa____ phi______ frames
    -       42.6857  -57.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   29.00   65.00   1.0000    1.1400
omega____ theta____ kappa____ phi______ frames
    -       42.6857  -38.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega   32.00   83.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
  4 omega  100.00  178.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000 -180.0000 78

#__ type_ start__ end____ width___ exp.time_
  5 omega  142.00  170.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  125.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega  138.00  171.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  125.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
  7 omega  119.00  170.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   45.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega  142.00  178.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  125.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
  9 omega   98.00  124.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  125.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   36.00   87.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
 11 omega   55.00   91.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
 12 omega   62.00  107.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
 13 omega   47.00  108.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  -60.0000 61

#__ type_ start__ end____ width___ exp.time_
 14 omega   88.00  115.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   45.00   86.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
 16 omega   32.00   62.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 17 omega   42.00   92.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00   89.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
 19 omega   36.00   66.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 20 omega  -26.00   61.00   1.0000    1.1400
omega____ theta____ kappa____ phi______ frames
    -       42.6857  -57.0000   90.0000 87

#__ type_ start__ end____ width___ exp.time_
 21 omega  -64.00   28.00   1.0000    1.1400
omega____ theta____ kappa____ phi______ frames
    -      -42.6857   77.0000  -30.0000 92

#__ type_ start__ end____ width___ exp.time_
 22 omega -113.00  -24.00   1.0000    1.1400
omega____ theta____ kappa____ phi______ frames
    -      -42.6857  -57.0000 -150.0000 89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0948540000
_diffrn_orient_matrix_UB_12      -0.1087267000
_diffrn_orient_matrix_UB_13      0.0716699000
_diffrn_orient_matrix_UB_21      -0.1228203000
_diffrn_orient_matrix_UB_22      0.1315601000
_diffrn_orient_matrix_UB_23      0.0502994000
_diffrn_orient_matrix_UB_31      -0.1735827000
_diffrn_orient_matrix_UB_32      -0.0658058000
_diffrn_orient_matrix_UB_33      0.0095943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3184
_reflns_number_total             3847
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3847
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+0.3684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1232
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C22(H22), C21(H21), C23(H23), C20(H20), C9(H9), C14(H14), C12(H12),
 C11(H11), C10(H10)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C6(H6A,H6B,H6C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.79462(17) -0.17181(13) 1.12464(7) 0.0224(3) Uani 1 1 d . . . . .
O4 O 0.84422(19) -0.32336(15) 1.23499(7) 0.0285(3) Uani 1 1 d . . . . .
O1 O 0.52079(18) 0.31518(14) 0.64115(7) 0.0287(3) Uani 1 1 d . . . . .
O2 O 0.22026(19) 0.45730(14) 0.58753(8) 0.0310(3) Uani 1 1 d . . . . .
C17 C 0.7580(2) -0.00303(19) 1.00900(10) 0.0208(3) Uani 1 1 d . . . . .
H17 H 0.7651 0.0760 1.0356 0.025 Uiso 1 1 calc R . . . .
N3 N 0.7313(2) 0.30006(16) 0.92423(8) 0.0231(3) Uani 1 1 d . . . . .
N1 N 0.6923(2) 0.38142(16) 0.80492(8) 0.0217(3) Uani 1 1 d . . . . .
C18 C 0.7725(2) -0.15079(19) 1.04697(9) 0.0200(3) Uani 1 1 d . . . . .
C19 C 0.7627(2) -0.27264(19) 1.00912(10) 0.0209(3) Uani 1 1 d . . . . .
C22 C 0.7812(2) -0.42230(19) 1.05326(10) 0.0225(3) Uani 1 1 d . . . . .
H22 H 0.7729 -0.5048 1.0296 0.027 Uiso 1 1 calc R . . . .
C15 C 0.7174(2) 0.18000(19) 0.88894(10) 0.0207(3) Uani 1 1 d . . . . .
C21 C 0.7230(2) -0.09633(19) 0.89167(10) 0.0227(3) Uani 1 1 d . . . . .
H21 H 0.7063 -0.0778 0.8393 0.027 Uiso 1 1 calc R . . . .
N2 N 0.7165(2) 0.42241(16) 0.87254(8) 0.0239(3) Uani 1 1 d . . . . .
C16 C 0.7329(2) 0.02522(18) 0.93082(10) 0.0199(3) Uani 1 1 d . . . . .
C24 C 0.8190(2) -0.3159(2) 1.16765(10) 0.0231(3) Uani 1 1 d . . . . .
C23 C 0.8105(2) -0.44319(19) 1.12838(10) 0.0237(3) Uani 1 1 d . . . . .
H23 H 0.8257 -0.5414 1.1559 0.028 Uiso 1 1 calc R . . . .
C20 C 0.7378(2) -0.24251(19) 0.93025(10) 0.0224(3) Uani 1 1 d . . . . .
H20 H 0.7312 -0.3217 0.9036 0.027 Uiso 1 1 calc R . . . .
C9 C 0.4085(3) 0.7463(2) 0.76888(10) 0.0269(4) Uani 1 1 d . . . . .
H9 H 0.5017 0.7559 0.7995 0.032 Uiso 1 1 calc R . . . .
C14 C 0.6917(2) 0.23236(18) 0.81260(10) 0.0215(3) Uani 1 1 d . . . . .
H14 H 0.6771 0.1768 0.7745 0.026 Uiso 1 1 calc R . . . .
C12 C 0.1324(3) 0.7197(2) 0.67751(10) 0.0261(4) Uani 1 1 d . . . . .
H12 H 0.0383 0.7123 0.6466 0.031 Uiso 1 1 calc R . . . .
C7 C 0.3240(3) 0.59851(19) 0.68178(9) 0.0228(3) Uani 1 1 d . . . . .
C11 C 0.0805(3) 0.8495(2) 0.71814(11) 0.0292(4) Uani 1 1 d . . . . .
H11 H -0.0468 0.9281 0.7140 0.035 Uiso 1 1 calc R . . . .
C8 C 0.4636(2) 0.61534(19) 0.72786(9) 0.0222(3) Uani 1 1 d . . . . .
C10 C 0.2176(3) 0.8626(2) 0.76496(11) 0.0300(4) Uani 1 1 d . . . . .
H10 H 0.1821 0.9482 0.7934 0.036 Uiso 1 1 calc R . . . .
C4 C 0.2805(3) 0.3053(2) 0.55759(11) 0.0286(4) Uani 1 1 d . . . . .
C1 C 0.4926(3) 0.2077(2) 0.59288(11) 0.0273(4) Uani 1 1 d . . . . .
B1 B 0.3576(3) 0.4535(2) 0.63638(12) 0.0245(4) Uani 1 1 d . . . . .
C13 C 0.6760(2) 0.4942(2) 0.73556(10) 0.0234(3) Uani 1 1 d . . . . .
H13A H 0.7139 0.4361 0.6911 0.028 Uiso 1 1 calc R . . . .
H13B H 0.7697 0.5491 0.7370 0.028 Uiso 1 1 calc R . . . .
C2 C 0.4934(3) 0.0606(2) 0.64605(14) 0.0442(5) Uani 1 1 d . . . . .
H2A H 0.6245 0.0081 0.6665 0.066 Uiso 1 1 calc GR . . . .
H2B H 0.4626 -0.0103 0.6180 0.066 Uiso 1 1 calc GR . . . .
H2C H 0.3937 0.0913 0.6872 0.066 Uiso 1 1 calc GR . . . .
C6 C 0.2838(4) 0.3355(3) 0.47204(13) 0.0547(7) Uani 1 1 d . . . . .
H6A H 0.1500 0.3975 0.4561 0.082 Uiso 1 1 calc GR . . . .
H6B H 0.3302 0.2360 0.4508 0.082 Uiso 1 1 calc GR . . . .
H6C H 0.3733 0.3922 0.4544 0.082 Uiso 1 1 calc GR . . . .
C3 C 0.6687(3) 0.1683(3) 0.53506(14) 0.0471(6) Uani 1 1 d . . . . .
H3A H 0.6744 0.2645 0.5063 0.071 Uiso 1 1 calc GR . . . .
H3B H 0.6522 0.1009 0.5010 0.071 Uiso 1 1 calc GR . . . .
H3C H 0.7919 0.1144 0.5610 0.071 Uiso 1 1 calc GR . . . .
C5 C 0.1150(3) 0.2376(3) 0.58737(17) 0.0517(6) Uani 1 1 d . . . . .
H5A H 0.1035 0.2303 0.6422 0.078 Uiso 1 1 calc GR . . . .
H5B H 0.1495 0.1338 0.5715 0.078 Uiso 1 1 calc GR . . . .
H5C H -0.0116 0.3062 0.5671 0.078 Uiso 1 1 calc GR . . . .


_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
O3 C18 1.377(2) . ?
O3 C24 1.381(2) . ?
O4 C24 1.211(2) . ?
O1 C1 1.460(2) . ?
O1 B1 1.367(2) . ?
O2 C4 1.450(2) . ?
O2 B1 1.354(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(2) . ?
C17 C16 1.388(2) . ?
N3 C15 1.368(2) . ?
N3 N2 1.317(2) . ?
N1 N2 1.345(2) . ?
N1 C14 1.345(2) . ?
N1 C13 1.470(2) . ?
C18 C19 1.397(2) . ?
C19 C22 1.440(2) . ?
C19 C20 1.399(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.341(2) . ?
C15 C16 1.468(2) . ?
C15 C14 1.374(2) . ?
C21 H21 0.9300 . ?
C21 C16 1.409(2) . ?
C21 C20 1.379(2) . ?
C24 C23 1.452(2) . ?
C23 H23 0.9300 . ?
C20 H20 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.395(2) . ?
C9 C10 1.387(3) . ?
C14 H14 0.9300 . ?
C12 H12 0.9300 . ?
C12 C7 1.409(2) . ?
C12 C11 1.384(3) . ?
C7 C8 1.405(2) . ?
C7 B1 1.571(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.385(3) . ?
C8 C13 1.518(2) . ?
C10 H10 0.9300 . ?
C4 C1 1.585(2) . ?
C4 C6 1.499(3) . ?
C4 C5 1.534(3) . ?
C1 C2 1.523(3) . ?
C1 C3 1.506(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

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
C18 O3 C24 121.73(13) . . ?
B1 O1 C1 108.90(13) . . ?
B1 O2 C4 109.75(13) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.15(15) . . ?
N2 N3 C15 108.58(14) . . ?
N2 N1 C13 119.84(13) . . ?
C14 N1 N2 110.90(14) . . ?
C14 N1 C13 129.24(14) . . ?
O3 C18 C17 116.77(14) . . ?
O3 C18 C19 121.00(14) . . ?
C17 C18 C19 122.23(15) . . ?
C18 C19 C22 118.17(15) . . ?
C18 C19 C20 117.97(15) . . ?
C20 C19 C22 123.85(15) . . ?
C19 C22 H22 119.9 . . ?
C23 C22 C19 120.22(15) . . ?
C23 C22 H22 119.9 . . ?
N3 C15 C16 122.05(15) . . ?
N3 C15 C14 108.10(14) . . ?
C14 C15 C16 129.84(15) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C16 120.69(16) . . ?
N3 N2 N1 107.46(13) . . ?
C17 C16 C15 120.53(14) . . ?
C17 C16 C21 119.43(15) . . ?
C21 C16 C15 120.04(15) . . ?
O3 C24 C23 117.34(15) . . ?
O4 C24 O3 116.49(15) . . ?
O4 C24 C23 126.16(16) . . ?
C22 C23 C24 121.44(15) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.54(15) . . ?
C21 C20 H20 119.7 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C10 C9 C8 121.38(16) . . ?
N1 C14 C15 104.95(14) . . ?
N1 C14 H14 127.5 . . ?
C15 C14 H14 127.5 . . ?
C7 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C7 121.71(16) . . ?
C12 C7 B1 116.19(15) . . ?
C8 C7 C12 117.56(15) . . ?
C8 C7 B1 126.22(15) . . ?
C12 C11 H11 119.9 . . ?
C12 C11 C10 120.16(16) . . ?
C10 C11 H11 119.9 . . ?
C9 C8 C7 120.03(15) . . ?
C9 C8 C13 117.70(15) . . ?
C7 C8 C13 122.27(15) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.13(16) . . ?
C11 C10 H10 120.4 . . ?
O2 C4 C1 103.69(13) . . ?
O2 C4 C6 107.95(16) . . ?
O2 C4 C5 105.33(16) . . ?
C6 C4 C1 115.43(17) . . ?
C6 C4 C5 110.1(2) . . ?
C5 C4 C1 113.49(16) . . ?
O1 C1 C4 103.83(13) . . ?
O1 C1 C2 105.92(15) . . ?
O1 C1 C3 107.31(15) . . ?
C2 C1 C4 113.37(15) . . ?
C3 C1 C4 114.52(17) . . ?
C3 C1 C2 111.06(18) . . ?
O1 B1 C7 125.34(16) . . ?
O2 B1 O1 113.68(15) . . ?
O2 B1 C7 120.98(16) . . ?
N1 C13 C8 112.10(13) . . ?
N1 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
C8 C13 H13A 109.2 . . ?
C8 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C18 C19 C22 -1.5(2) . . . . ?
O3 C18 C19 C20 179.28(14) . . . . ?
O3 C24 C23 C22 0.3(2) . . . . ?
O4 C24 C23 C22 179.84(16) . . . . ?
O2 C4 C1 O1 2.45(18) . . . . ?
O2 C4 C1 C2 116.91(17) . . . . ?
O2 C4 C1 C3 -114.23(18) . . . . ?
C17 C18 C19 C22 179.38(14) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
N3 C15 C16 C17 1.5(2) . . . . ?
N3 C15 C16 C21 -178.33(14) . . . . ?
N3 C15 C14 N1 0.32(17) . . . . ?
C18 O3 C24 O4 177.49(14) . . . . ?
C18 O3 C24 C23 -3.0(2) . . . . ?
C18 C17 C16 C15 -179.91(14) . . . . ?
C18 C17 C16 C21 -0.1(2) . . . . ?
C18 C19 C22 C23 -1.1(2) . . . . ?
C18 C19 C20 C21 -0.2(2) . . . . ?
C19 C22 C23 C24 1.6(2) . . . . ?
C22 C19 C20 C21 -179.38(15) . . . . ?
C15 N3 N2 N1 0.30(17) . . . . ?
N2 N3 C15 C16 178.63(14) . . . . ?
N2 N3 C15 C14 -0.39(18) . . . . ?
N2 N1 C14 C15 -0.15(18) . . . . ?
N2 N1 C13 C8 -81.81(18) . . . . ?
C16 C17 C18 O3 -179.16(13) . . . . ?
C16 C17 C18 C19 0.0(2) . . . . ?
C16 C15 C14 N1 -178.60(15) . . . . ?
C16 C21 C20 C19 0.1(2) . . . . ?
C24 O3 C18 C17 -177.25(13) . . . . ?
C24 O3 C18 C19 3.6(2) . . . . ?
C20 C19 C22 C23 178.09(15) . . . . ?
C20 C21 C16 C17 0.0(2) . . . . ?
C20 C21 C16 C15 179.86(14) . . . . ?
C9 C8 C13 N1 81.84(18) . . . . ?
C14 N1 N2 N3 -0.09(18) . . . . ?
C14 N1 C13 C8 99.97(19) . . . . ?
C14 C15 C16 C17 -179.72(16) . . . . ?
C14 C15 C16 C21 0.5(3) . . . . ?
C12 C7 C8 C9 1.7(2) . . . . ?
C12 C7 C8 C13 -178.69(15) . . . . ?
C12 C7 B1 O1 -170.75(17) . . . . ?
C12 C7 B1 O2 9.2(2) . . . . ?
C12 C11 C10 C9 1.7(3) . . . . ?
C7 C12 C11 C10 -0.4(3) . . . . ?
C7 C8 C13 N1 -97.79(18) . . . . ?
C11 C12 C7 C8 -1.3(3) . . . . ?
C11 C12 C7 B1 176.57(16) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C8 C7 B1 O1 6.9(3) . . . . ?
C8 C7 B1 O2 -173.17(16) . . . . ?
C10 C9 C8 C7 -0.5(3) . . . . ?
C10 C9 C8 C13 179.89(16) . . . . ?
C4 O2 B1 O1 4.0(2) . . . . ?
C4 O2 B1 C7 -175.92(15) . . . . ?
C1 O1 B1 O2 -2.3(2) . . . . ?
C1 O1 B1 C7 177.69(16) . . . . ?
B1 O1 C1 C4 -0.29(19) . . . . ?
B1 O1 C1 C2 -119.96(17) . . . . ?
B1 O1 C1 C3 121.34(18) . . . . ?
B1 O2 C4 C1 -3.85(19) . . . . ?
B1 O2 C4 C6 -126.77(18) . . . . ?
B1 O2 C4 C5 115.62(18) . . . . ?
B1 C7 C8 C9 -175.90(16) . . . . ?
B1 C7 C8 C13 3.7(3) . . . . ?
C13 N1 N2 N3 -178.61(13) . . . . ?
C13 N1 C14 C15 178.20(15) . . . . ?
C6 C4 C1 O1 120.29(19) . . . . ?
C6 C4 C1 C2 -125.2(2) . . . . ?
C6 C4 C1 C3 3.6(2) . . . . ?
C5 C4 C1 O1 -111.28(18) . . . . ?
C5 C4 C1 C2 3.2(2) . . . . ?
C5 C4 C1 C3 132.0(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4 -1 0 0.0846 -4.0000 -1.0000 0.0001 -0.2707 0.3597 0.7601
4 0 0 0.0745 4.0000 0.0000 -0.0000 0.3794 -0.4913 -0.6943
-1 -6 0 0.0919 -1.0000 -6.0000 0.0001 0.5575 -0.6665 0.5684
0 0 -11 0.0131 0.0000 0.0000 -11.0000 -0.7884 -0.5533 -0.1055
0 0 11 0.0151 -0.0000 -0.0000 11.0000 0.7884 0.5533 0.1055
-1 4 6 0.0820 -1.0000 4.0000 6.0000 -0.0997 0.9509 -0.0321
0 6 1 0.0837 -0.0000 6.0000 0.9999 -0.5807 0.8397 -0.3852
4 4 0 0.1115 4.0000 4.0000 -0.0001 -0.0555 0.0350 -0.9576

_olex2_submission_special_instructions 'No special instructions were received'
