# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ca493d
_database_code_depnum_ccdc_archive 'CCDC 1856403'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Aix Marseille Universit?
France
;
_audit_update_record             
;
2018-07-17 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;
_audit_creation_date             2017-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H31 B N2'
_chemical_formula_sum            'C24 H31 B N2'
_chemical_formula_weight         358.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?

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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.55860(10)
_cell_length_b                   9.20850(10)
_cell_length_c                   30.8403(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2146.59(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5675
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.7780
_cell_measurement_theta_min      4.3500
_shelx_estimated_absorpt_T_max   0.902
_shelx_estimated_absorpt_T_min   0.854
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
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    1.109
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0112
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7385
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.926
_diffrn_reflns_theta_min         5.012
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00   4.00   1.00    1.00    --  -17.77 -19.00 -60.00  102
  2  ω    -78.00 -20.00   1.00    1.00    --  -17.77 -38.00-120.00   58
  3  ω     56.00  96.00   1.00    1.00    --   17.77-178.00-120.00   40
  4  ω     31.00 119.00   1.00   10.00    --  101.41 -61.00 -90.00   88
  5  ω    104.00 174.00   1.00   10.00    --  101.41 125.00 -30.00   70
  6  ω     95.00 121.00   1.00   10.00    --  101.41  30.00-120.00   26
  7  ω     30.00 130.00   1.00   10.00    --  101.41 -30.00  60.00  100
  8  ω    147.00 173.00   1.00   10.00    --  101.41  30.00-120.00   26
  9  ω     22.00 121.00   1.00   10.00    --  101.41 -15.00-180.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1830659000
_diffrn_orient_matrix_UB_12      0.0614640000
_diffrn_orient_matrix_UB_13      0.0120733000
_diffrn_orient_matrix_UB_21      -0.0895794000
_diffrn_orient_matrix_UB_22      -0.1261723000
_diffrn_orient_matrix_UB_23      -0.0243856000
_diffrn_orient_matrix_UB_31      0.0006120000
_diffrn_orient_matrix_UB_32      -0.0909826000
_diffrn_orient_matrix_UB_33      0.0419084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                3944
_reflns_number_total             4047
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4047
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0687P)²+0.1637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1205
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), B3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C8(H8), C10(H10), C18(H18), C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2729(2) 0.24915(18) 0.61957(5) 0.0483(4) Uani 1 1 d . . . . .
N2 N 0.3746(2) 0.0487(2) 0.64454(6) 0.0523(4) Uani 1 1 d . . . . .
C1 C 0.1290(3) 0.1655(3) 0.63153(8) 0.0597(6) Uani 1 1 d . . . . .
H1 H 0.010408 0.191147 0.629042 0.072 Uiso 1 1 calc R . . . .
C2 C 0.1929(3) 0.0401(3) 0.64745(8) 0.0600(5) Uani 1 1 d . . . . .
H2 H 0.127344 -0.037332 0.658294 0.072 Uiso 1 1 calc R . . . .
C3 C 0.5222(3) -0.0487(3) 0.65604(9) 0.0606(6) Uani 1 1 d . . . . .
H3A H 0.505208 -0.144464 0.643597 0.073 Uiso 1 1 calc R . . . .
H3B H 0.533398 -0.057930 0.687254 0.073 Uiso 1 1 calc R . . . .
C4 C 0.6869(3) 0.0262(2) 0.63641(7) 0.0517(5) Uani 1 1 d . . . . .
H4 H 0.784829 0.024245 0.657235 0.062 Uiso 1 1 calc R . . . .
C5 C 0.4235(3) 0.1768(2) 0.62792(6) 0.0453(4) Uani 1 1 d . . . . .
C6 C 0.2646(3) 0.3859(2) 0.59690(6) 0.0474(4) Uani 1 1 d . . . . .
C7 C 0.2599(3) 0.5140(2) 0.62068(7) 0.0546(5) Uani 1 1 d . . . . .
C8 C 0.2486(4) 0.6424(3) 0.59718(9) 0.0672(6) Uani 1 1 d . . . . .
H8 H 0.242896 0.729637 0.612286 0.081 Uiso 1 1 calc R . . . .
C9 C 0.2455(4) 0.6463(3) 0.55253(10) 0.0738(7) Uani 1 1 d . . . . .
C10 C 0.2537(4) 0.5157(3) 0.53060(8) 0.0724(7) Uani 1 1 d . . . . .
H10 H 0.253881 0.516563 0.500443 0.087 Uiso 1 1 calc R . . . .
C11 C 0.2615(3) 0.3839(3) 0.55189(7) 0.0579(5) Uani 1 1 d . . . . .
C12 C 0.2682(5) 0.2422(3) 0.52735(9) 0.0854(9) Uani 1 1 d . . . . .
H12A H 0.368918 0.186964 0.536741 0.128 Uiso 1 1 calc GR . . . .
H12B H 0.277926 0.261523 0.496855 0.128 Uiso 1 1 calc GR . . . .
H12C H 0.162129 0.187899 0.532843 0.128 Uiso 1 1 calc GR . . . .
C13 C 0.2673(4) 0.5134(3) 0.66914(8) 0.0758(7) Uani 1 1 d . . . . .
H13A H 0.181401 0.446217 0.680246 0.114 Uiso 1 1 calc GR . . . .
H13B H 0.242067 0.609008 0.679868 0.114 Uiso 1 1 calc GR . . . .
H13C H 0.383361 0.484478 0.678421 0.114 Uiso 1 1 calc GR . . . .
C14 C 0.2329(7) 0.7889(4) 0.52852(16) 0.1171(14) Uani 1 1 d . . . . .
H14A H 0.169976 0.858090 0.545981 0.176 Uiso 1 1 calc GR . . . .
H14B H 0.170884 0.774520 0.501696 0.176 Uiso 1 1 calc GR . . . .
H14C H 0.349682 0.824774 0.522634 0.176 Uiso 1 1 calc GR . . . .
C15 C 0.7396(4) -0.0528(3) 0.59509(9) 0.0741(7) Uani 1 1 d . . . . .
H15A H 0.762751 -0.153007 0.601565 0.111 Uiso 1 1 calc GR . . . .
H15B H 0.844229 -0.008983 0.583241 0.111 Uiso 1 1 calc GR . . . .
H15C H 0.645154 -0.046376 0.574372 0.111 Uiso 1 1 calc GR . . . .
C16 C 0.7009(2) 0.3361(2) 0.65383(6) 0.0441(4) Uani 1 1 d . . . . .
C17 C 0.6961(3) 0.3381(2) 0.69979(6) 0.0502(5) Uani 1 1 d . . . . .
C18 C 0.7499(3) 0.4601(3) 0.72316(7) 0.0573(5) Uani 1 1 d . . . . .
H18 H 0.745261 0.457183 0.753284 0.069 Uiso 1 1 calc R . . . .
C19 C 0.8096(3) 0.5844(3) 0.70331(8) 0.0582(5) Uani 1 1 d . . . . .
C20 C 0.8144(3) 0.5843(2) 0.65858(8) 0.0575(5) Uani 1 1 d . . . . .
H20 H 0.854654 0.667017 0.644374 0.069 Uiso 1 1 calc R . . . .
C21 C 0.7615(3) 0.4655(2) 0.63385(6) 0.0492(4) Uani 1 1 d . . . . .
C22 C 0.8674(5) 0.7167(3) 0.72897(10) 0.0803(8) Uani 1 1 d . . . . .
H22A H 0.777436 0.790070 0.727287 0.121 Uiso 1 1 calc GR . . . .
H22B H 0.975799 0.753774 0.717144 0.121 Uiso 1 1 calc GR . . . .
H22C H 0.885419 0.689883 0.758729 0.121 Uiso 1 1 calc GR . . . .
C23 C 0.7702(4) 0.4831(3) 0.58518(7) 0.0640(6) Uani 1 1 d . . . . .
H23A H 0.843556 0.408233 0.573106 0.096 Uiso 1 1 calc GR . . . .
H23B H 0.819401 0.576430 0.578268 0.096 Uiso 1 1 calc GR . . . .
H23C H 0.653257 0.475929 0.573241 0.096 Uiso 1 1 calc GR . . . .
C25 C 0.6281(4) 0.2112(3) 0.72549(7) 0.0693(7) Uani 1 1 d . . . . .
H25A H 0.512356 0.185211 0.715302 0.104 Uiso 1 1 calc GR . . . .
H25B H 0.621796 0.237192 0.755596 0.104 Uiso 1 1 calc GR . . . .
H25C H 0.706718 0.130175 0.721985 0.104 Uiso 1 1 calc GR . . . .
B3 B 0.6334(3) 0.1990(3) 0.62446(7) 0.0447(5) Uani 1 1 d . . . . .
H3 H 0.664015 0.217719 0.594092 0.054 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.383(3) . ?
N1 C5 1.344(3) . ?
N1 C6 1.442(3) . ?
N2 C2 1.379(3) . ?
N2 C3 1.476(3) . ?
N2 C5 1.338(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.345(4) . ?
C2 H2 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.547(3) . ?
C4 H4 0.9800 . ?
C4 C15 1.521(3) . ?
C4 B3 1.682(3) . ?
C5 B3 1.604(3) . ?
C6 C7 1.389(3) . ?
C6 C11 1.388(3) . ?
C7 C8 1.389(3) . ?
C7 C13 1.496(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(4) . ?
C9 C10 1.381(4) . ?
C9 C14 1.510(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(4) . ?
C11 C12 1.510(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.418(3) . ?
C16 C21 1.418(3) . ?
C16 B3 1.636(3) . ?
C17 C18 1.395(3) . ?
C17 C25 1.503(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.374(3) . ?
C19 C20 1.380(3) . ?
C19 C22 1.517(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.392(3) . ?
C21 C23 1.511(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
B3 H3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C6 125.57(17) . . ?
C5 N1 C1 109.82(17) . . ?
C5 N1 C6 124.24(17) . . ?
C2 N2 C3 134.6(2) . . ?
C5 N2 C2 110.6(2) . . ?
C5 N2 C3 114.78(17) . . ?
N1 C1 H1 126.5 . . ?
C2 C1 N1 107.07(19) . . ?
C2 C1 H1 126.5 . . ?
N2 C2 H2 126.7 . . ?
C1 C2 N2 106.5(2) . . ?
C1 C2 H2 126.7 . . ?
N2 C3 H3A 110.9 . . ?
N2 C3 H3B 110.9 . . ?
N2 C3 C4 104.08(17) . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C3 C4 H4 110.0 . . ?
C3 C4 B3 108.31(17) . . ?
C15 C4 C3 109.0(2) . . ?
C15 C4 H4 110.0 . . ?
C15 C4 B3 109.39(18) . . ?
B3 C4 H4 110.0 . . ?
N1 C5 B3 139.70(19) . . ?
N2 C5 N1 106.03(17) . . ?
N2 C5 B3 114.26(17) . . ?
C7 C6 N1 119.12(17) . . ?
C11 C6 N1 118.29(18) . . ?
C11 C6 C7 122.6(2) . . ?
C6 C7 C13 121.6(2) . . ?
C8 C7 C6 116.6(2) . . ?
C8 C7 C13 121.8(2) . . ?
C7 C8 H8 118.5 . . ?
C9 C8 C7 123.0(2) . . ?
C9 C8 H8 118.5 . . ?
C8 C9 C10 117.7(2) . . ?
C8 C9 C14 120.9(3) . . ?
C10 C9 C14 121.3(3) . . ?
C9 C10 H10 118.9 . . ?
C9 C10 C11 122.3(2) . . ?
C11 C10 H10 118.9 . . ?
C6 C11 C12 120.8(2) . . ?
C10 C11 C6 117.7(2) . . ?
C10 C11 C12 121.5(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 B3 123.74(17) . . ?
C21 C16 C17 115.59(18) . . ?
C21 C16 B3 120.61(16) . . ?
C16 C17 C25 121.73(19) . . ?
C18 C17 C16 121.28(19) . . ?
C18 C17 C25 116.97(18) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 C17 122.4(2) . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C20 117.0(2) . . ?
C18 C19 C22 122.1(2) . . ?
C20 C19 C22 121.0(2) . . ?
C19 C20 H20 118.6 . . ?
C19 C20 C21 122.7(2) . . ?
C21 C20 H20 118.6 . . ?
C16 C21 C23 122.41(18) . . ?
C20 C21 C16 120.99(18) . . ?
C20 C21 C23 116.59(18) . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17 C25 H25A 109.5 . . ?
C17 C25 H25B 109.5 . . ?
C17 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C4 B3 H3 108.6 . . ?
C5 B3 C4 95.93(16) . . ?
C5 B3 C16 111.72(17) . . ?
C5 B3 H3 108.6 . . ?
C16 B3 C4 122.26(17) . . ?
C16 B3 H3 108.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -0.6(3) . . . . ?
N1 C5 B3 C4 -171.1(2) . . . . ?
N1 C5 B3 C16 60.6(3) . . . . ?
N1 C6 C7 C8 -178.8(2) . . . . ?
N1 C6 C7 C13 1.4(3) . . . . ?
N1 C6 C11 C10 -179.9(2) . . . . ?
N1 C6 C11 C12 -0.5(4) . . . . ?
N2 C3 C4 C15 -103.2(2) . . . . ?
N2 C3 C4 B3 15.8(2) . . . . ?
N2 C5 B3 C4 9.9(2) . . . . ?
N2 C5 B3 C16 -118.37(19) . . . . ?
C1 N1 C5 N2 0.6(2) . . . . ?
C1 N1 C5 B3 -178.5(3) . . . . ?
C1 N1 C6 C7 92.3(3) . . . . ?
C1 N1 C6 C11 -87.6(3) . . . . ?
C2 N2 C3 C4 171.3(2) . . . . ?
C2 N2 C5 N1 -0.9(2) . . . . ?
C2 N2 C5 B3 178.41(19) . . . . ?
C3 N2 C2 C1 179.9(2) . . . . ?
C3 N2 C5 N1 179.91(19) . . . . ?
C3 N2 C5 B3 -0.8(3) . . . . ?
C3 C4 B3 C5 -15.1(2) . . . . ?
C3 C4 B3 C16 105.2(2) . . . . ?
C5 N1 C1 C2 0.0(3) . . . . ?
C5 N1 C6 C7 -95.4(2) . . . . ?
C5 N1 C6 C11 84.7(3) . . . . ?
C5 N2 C2 C1 0.9(3) . . . . ?
C5 N2 C3 C4 -9.9(3) . . . . ?
C6 N1 C1 C2 173.26(19) . . . . ?
C6 N1 C5 N2 -172.80(17) . . . . ?
C6 N1 C5 B3 8.1(4) . . . . ?
C6 C7 C8 C9 -1.3(4) . . . . ?
C7 C6 C11 C10 0.1(4) . . . . ?
C7 C6 C11 C12 179.5(3) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C7 C8 C9 C14 179.9(3) . . . . ?
C8 C9 C10 C11 1.1(5) . . . . ?
C9 C10 C11 C6 -1.3(4) . . . . ?
C9 C10 C11 C12 179.3(3) . . . . ?
C11 C6 C7 C8 1.1(3) . . . . ?
C11 C6 C7 C13 -178.6(2) . . . . ?
C13 C7 C8 C9 178.5(2) . . . . ?
C14 C9 C10 C11 -178.6(3) . . . . ?
C15 C4 B3 C5 103.5(2) . . . . ?
C15 C4 B3 C16 -136.1(2) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C16 C21 C20 0.9(3) . . . . ?
C17 C16 C21 C23 -178.3(2) . . . . ?
C17 C16 B3 C4 -45.0(3) . . . . ?
C17 C16 B3 C5 67.5(2) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C17 C18 C19 C22 179.8(2) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C19 C20 C21 C16 -0.7(3) . . . . ?
C19 C20 C21 C23 178.6(2) . . . . ?
C21 C16 C17 C18 -0.7(3) . . . . ?
C21 C16 C17 C25 177.5(2) . . . . ?
C21 C16 B3 C4 138.0(2) . . . . ?
C21 C16 B3 C5 -109.5(2) . . . . ?
C22 C19 C20 C21 -179.6(2) . . . . ?
C25 C17 C18 C19 -178.0(2) . . . . ?
B3 C16 C17 C18 -177.80(19) . . . . ?
B3 C16 C17 C25 0.4(3) . . . . ?
B3 C16 C21 C20 178.14(19) . . . . ?
B3 C16 C21 C23 -1.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.315
_oxdiff_exptl_absorpt_empirical_full_min 0.760
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/pentane'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_ca582d
_database_code_depnum_ccdc_archive 'CCDC 1857909'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Aix Marseille Universit?
France
;
_audit_update_record             
;
2018-07-24 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;
_audit_creation_date             2018-01-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H29 B N2'
_chemical_formula_sum            'C23 H29 B N2'
_chemical_formula_weight         344.29
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c23 h29 b1 n2'
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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.56120(10)
_cell_length_b                   15.4461(2)
_cell_length_c                   15.9652(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2111.19(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5377
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.8040
_cell_measurement_theta_min      5.6890
_shelx_estimated_absorpt_T_max   0.912
_shelx_estimated_absorpt_T_min   0.864
_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
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    1.083
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7375
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.053
_diffrn_reflns_theta_min         3.982
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  22.00   1.00    1.00    --  -17.77 -19.00 120.00   26
  2  ω    -23.00  57.00   1.00    1.00    --  -17.77  38.00 -60.00   80
  3  ω    -89.00 -13.00   1.00    1.00    --  -17.77 -19.00 120.00   76
  4  ω     74.00 104.00   1.00    1.00    --   17.77-178.00 150.00   30
  5  ω     95.00 171.00   1.00   10.00    --  101.41 125.00   0.00   76
  6  ω     97.00 138.00   1.00   10.00    --  101.41 125.00-180.00   41
  7  ω     75.00 171.00   1.00   10.00    --  101.41  61.00  60.00   96
  8  ω    110.00 158.00   1.00   10.00    --  101.41 125.00-150.00   48
  9  ω     35.00  86.00   1.00   10.00    --  101.41-125.00  30.00   51
 10  ω     30.00 126.00   1.00   10.00    --  101.41 -45.00 -90.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0228231000
_diffrn_orient_matrix_UB_12      0.0153195000
_diffrn_orient_matrix_UB_13      0.0945465000
_diffrn_orient_matrix_UB_21      -0.1332759000
_diffrn_orient_matrix_UB_22      0.0669350000
_diffrn_orient_matrix_UB_23      -0.0010838000
_diffrn_orient_matrix_UB_31      -0.1187447000
_diffrn_orient_matrix_UB_32      -0.0723763000
_diffrn_orient_matrix_UB_33      0.0191069000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                3850
_reflns_number_total             3980
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details 
;
 Flack x determined using 1582 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0756P)²+0.0757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1107
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), B1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C15(H15A,H15B,
 H15C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.48473(17) 0.56235(9) 0.22861(9) 0.0489(3) Uani 1 1 d . . . . .
N2 N 0.64133(18) 0.64326(11) 0.15928(10) 0.0565(4) Uani 1 1 d . . . . .
C1 C 0.50686(19) 0.64378(11) 0.20123(10) 0.0464(3) Uani 1 1 d . . . . .
C2 C 0.6086(3) 0.51044(14) 0.20217(15) 0.0669(5) Uani 1 1 d . . . . .
H2 H 0.621458 0.451653 0.212703 0.080 Uiso 1 1 calc R . . . .
C3 C 0.7051(3) 0.56154(15) 0.15875(16) 0.0724(6) Uani 1 1 d . . . . .
H3 H 0.797923 0.544963 0.133051 0.087 Uiso 1 1 calc R . . . .
C4 C 0.3490(2) 0.53384(10) 0.27369(10) 0.0466(4) Uani 1 1 d . . . . .
C5 C 0.3516(2) 0.53415(11) 0.36103(11) 0.0555(4) Uani 1 1 d . . . . .
C6 C 0.2183(3) 0.50520(15) 0.40228(12) 0.0674(5) Uani 1 1 d . . . . .
H6 H 0.217592 0.504856 0.460527 0.081 Uiso 1 1 calc R . . . .
C7 C 0.0876(3) 0.47708(14) 0.36022(14) 0.0676(5) Uani 1 1 d . . . . .
C8 C 0.0893(2) 0.47868(14) 0.27330(13) 0.0634(5) Uani 1 1 d . . . . .
H8 H 0.001472 0.460052 0.244108 0.076 Uiso 1 1 calc R . . . .
C9 C 0.2182(2) 0.50727(12) 0.22896(11) 0.0526(4) Uani 1 1 d . . . . .
C10 C 0.4920(3) 0.56477(18) 0.40916(14) 0.0812(7) Uani 1 1 d . . . . .
H10A H 0.585125 0.542792 0.383328 0.122 Uiso 1 1 calc GR . . . .
H10B H 0.485771 0.544180 0.465800 0.122 Uiso 1 1 calc GR . . . .
H10C H 0.494631 0.626905 0.409110 0.122 Uiso 1 1 calc GR . . . .
C11 C -0.0546(4) 0.4445(3) 0.4070(2) 0.1081(10) Uani 1 1 d . . . . .
H11A H -0.048901 0.382656 0.412262 0.162 Uiso 1 1 calc GR . . . .
H11B H -0.147303 0.459908 0.376605 0.162 Uiso 1 1 calc GR . . . .
H11C H -0.057754 0.470227 0.461671 0.162 Uiso 1 1 calc GR . . . .
C12 C 0.2170(3) 0.50965(17) 0.13471(12) 0.0744(6) Uani 1 1 d . . . . .
H12A H 0.206802 0.568469 0.116083 0.112 Uiso 1 1 calc GR . . . .
H12B H 0.130624 0.476196 0.114179 0.112 Uiso 1 1 calc GR . . . .
H12C H 0.312916 0.485790 0.113744 0.112 Uiso 1 1 calc GR . . . .
C13 C 0.6890(3) 0.72758(15) 0.12538(15) 0.0706(6) Uani 1 1 d . . . . .
H13A H 0.710554 0.723209 0.065878 0.085 Uiso 1 1 calc R . . . .
H13B H 0.782074 0.748443 0.153566 0.085 Uiso 1 1 calc R . . . .
C14 C 0.5503(2) 0.78880(12) 0.14142(12) 0.0575(4) Uani 1 1 d . . . . .
H14 H 0.587504 0.840127 0.171499 0.069 Uiso 1 1 calc R . . . .
C15 C 0.4805(4) 0.8165(2) 0.05849(16) 0.0888(8) Uani 1 1 d . . . . .
H15A H 0.557523 0.847346 0.026552 0.133 Uiso 1 1 calc GR . . . .
H15B H 0.392316 0.853502 0.068482 0.133 Uiso 1 1 calc GR . . . .
H15C H 0.447367 0.766282 0.027865 0.133 Uiso 1 1 calc GR . . . .
C16 C 0.3821(2) 0.77134(10) 0.29492(12) 0.0508(4) Uani 1 1 d . . . . .
C17 C 0.4994(2) 0.79249(11) 0.35345(12) 0.0566(4) Uani 1 1 d . . . . .
C18 C 0.4628(4) 0.82417(15) 0.43268(15) 0.0766(6) Uani 1 1 d . . . . .
H18 H 0.542675 0.837639 0.469976 0.092 Uiso 1 1 calc R . . . .
C19 C 0.3093(4) 0.83577(18) 0.45641(18) 0.0937(9) Uani 1 1 d . . . . .
H19 H 0.285075 0.858424 0.508799 0.112 Uiso 1 1 calc R . . . .
C20 C 0.1936(4) 0.81349(17) 0.4018(2) 0.0902(9) Uani 1 1 d . . . . .
H20 H 0.090055 0.820497 0.418050 0.108 Uiso 1 1 calc R . . . .
C21 C 0.2257(2) 0.78058(13) 0.32251(17) 0.0694(6) Uani 1 1 d . . . . .
C22 C 0.6707(2) 0.77980(15) 0.33451(14) 0.0647(5) Uani 1 1 d . . . . .
H22A H 0.687055 0.722556 0.312794 0.097 Uiso 1 1 calc GR . . . .
H22B H 0.730351 0.787086 0.384941 0.097 Uiso 1 1 calc GR . . . .
H22C H 0.703630 0.821698 0.293753 0.097 Uiso 1 1 calc GR . . . .
C23 C 0.0888(3) 0.7518(2) 0.2695(2) 0.0997(10) Uani 1 1 d . . . . .
H23A H 0.089774 0.782687 0.217337 0.150 Uiso 1 1 calc GR . . . .
H23B H -0.006817 0.763742 0.298719 0.150 Uiso 1 1 calc GR . . . .
H23C H 0.096647 0.690814 0.258901 0.150 Uiso 1 1 calc GR . . . .
B1 B 0.4211(2) 0.73586(12) 0.20158(13) 0.0499(4) Uani 1 1 d . . . . .
H1 H 0.322885 0.730510 0.170490 0.060 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.345(2) . ?
N1 C2 1.395(2) . ?
N1 C4 1.436(2) . ?
N2 C1 1.332(2) . ?
N2 C3 1.375(3) . ?
N2 C13 1.468(3) . ?
C1 B1 1.601(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.337(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(2) . ?
C4 C9 1.390(2) . ?
C5 C6 1.391(3) . ?
C5 C10 1.502(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(3) . ?
C7 C8 1.388(3) . ?
C7 C11 1.514(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(3) . ?
C9 C12 1.505(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.540(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.515(3) . ?
C14 B1 1.678(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.410(3) . ?
C16 C21 1.417(2) . ?
C16 B1 1.623(3) . ?
C17 C18 1.392(3) . ?
C17 C22 1.510(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.364(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.392(4) . ?
C21 C23 1.512(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
B1 H1 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 109.40(16) . . ?
C1 N1 C4 124.30(14) . . ?
C2 N1 C4 126.20(15) . . ?
C1 N2 C3 110.60(17) . . ?
C1 N2 C13 114.86(16) . . ?
C3 N2 C13 134.53(16) . . ?
N1 C1 B1 139.93(15) . . ?
N2 C1 N1 106.23(15) . . ?
N2 C1 B1 113.80(15) . . ?
N1 C2 H2 126.6 . . ?
C3 C2 N1 106.72(18) . . ?
C3 C2 H2 126.6 . . ?
N2 C3 H3 126.5 . . ?
C2 C3 N2 107.04(17) . . ?
C2 C3 H3 126.5 . . ?
C5 C4 N1 119.14(16) . . ?
C9 C4 N1 119.00(14) . . ?
C9 C4 C5 121.86(17) . . ?
C4 C5 C10 121.70(19) . . ?
C6 C5 C4 117.31(17) . . ?
C6 C5 C10 120.99(17) . . ?
C5 C6 H6 118.7 . . ?
C7 C6 C5 122.53(17) . . ?
C7 C6 H6 118.7 . . ?
C6 C7 C8 118.30(19) . . ?
C6 C7 C11 121.2(2) . . ?
C8 C7 C11 120.5(2) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.68(19) . . ?
C9 C8 H8 119.2 . . ?
C4 C9 C12 120.79(18) . . ?
C8 C9 C4 118.29(16) . . ?
C8 C9 C12 120.91(18) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 110.6 . . ?
N2 C13 H13B 110.6 . . ?
N2 C13 C14 105.61(15) . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 H13A 110.6 . . ?
C14 C13 H13B 110.6 . . ?
C13 C14 H14 109.1 . . ?
C13 C14 B1 107.72(15) . . ?
C15 C14 C13 109.44(19) . . ?
C15 C14 H14 109.1 . . ?
C15 C14 B1 112.21(18) . . ?
B1 C14 H14 109.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 116.34(18) . . ?
C17 C16 B1 122.70(15) . . ?
C21 C16 B1 120.94(19) . . ?
C16 C17 C22 121.92(16) . . ?
C18 C17 C16 121.6(2) . . ?
C18 C17 C22 116.5(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 118.9(2) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 H20 119.0 . . ?
C19 C20 C21 122.0(2) . . ?
C21 C20 H20 119.0 . . ?
C16 C21 C23 121.9(2) . . ?
C20 C21 C16 120.4(2) . . ?
C20 C21 C23 117.6(2) . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 B1 C14 97.40(13) . . ?
C1 B1 C16 113.44(14) . . ?
C1 B1 H1 108.5 . . ?
C14 B1 H1 108.5 . . ?
C16 B1 C14 119.79(15) . . ?
C16 B1 H1 108.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.895
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichlorometane/pentane'
####################################################################### 
# 
# 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_ca609d
_database_code_depnum_ccdc_archive 'CCDC 1857908'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Aix Marseille Universit?
France
;
_audit_update_record             
;
2018-07-24 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;
_audit_creation_date             2018-02-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H29 B N2 O'
_chemical_formula_sum            'C23 H29 B N2 O'
_chemical_formula_weight         360.29
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c23 h29 b1 n2 o1'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.76550(10)
_cell_length_b                   12.17080(10)
_cell_length_c                   22.3907(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2116.20(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17277
_cell_measurement_temperature    293
_cell_measurement_theta_max      74.0600
_cell_measurement_theta_min      3.5650
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.817
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
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    1.131
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24338
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.440
_diffrn_reflns_theta_min         3.949
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    2.00    --  -41.26 -38.00   0.00   99
  2  ω    -96.00  -2.00   1.00    2.00    --  -41.26 125.00 -60.00   94
  3  ω     23.00  97.00   1.00    2.00    --   41.26-125.00-180.00   74
  4  ω     25.00 109.00   1.00   10.00    --  107.87 -94.00  30.00   84
  5  ω     35.00 122.00   1.00   10.00    --  107.87-125.00-120.00   87
  6  ω     94.00 178.00   1.00   10.00    --  107.87 125.00 -60.00   84
  7  ω     75.00 178.00   1.00   10.00    --  107.87  77.00 120.00  103
  8  ω     55.00 178.00   1.00   10.00    --  107.87  15.00-120.00  123
  9  ω   -113.00 -13.00   1.00    2.00    --  -41.26 -57.00 -90.00  100
 10  ω   -113.00 -13.00   1.00    2.00    --  -41.26 -57.00 120.00  100
 11  ω     79.00 178.00   1.00   10.00    --  107.87  61.00  30.00   99
 12  ω     75.00 178.00   1.00   10.00    --  107.87  77.00  60.00  103
 13  ω     35.00 134.00   1.00   10.00    --  107.87 -45.00   0.00   99
 14  ω     82.00 178.00   1.00   10.00    --  107.87  45.00 -60.00   96
 15  ω   -117.00  -9.00   1.00    2.00    --  -41.26 -77.00-120.00  108
 16  ω      1.00  82.00   1.00    2.00    --   41.26 -99.00-120.00   81
 17  ω     82.00 178.00   1.00   10.00    --  107.87  45.00   0.00   96
 18  ω     75.00 178.00   1.00   10.00    --  107.87  77.00-120.00  103
 19  ω     75.00 146.00   1.00   10.00    --  107.87  77.00  90.00   71
 20  ω     25.00 109.00   1.00   10.00    --  107.87 -94.00 -90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1439946000
_diffrn_orient_matrix_UB_12      0.0127411000
_diffrn_orient_matrix_UB_13      -0.0467979000
_diffrn_orient_matrix_UB_21      0.1279845000
_diffrn_orient_matrix_UB_22      -0.0560952000
_diffrn_orient_matrix_UB_23      0.0428257000
_diffrn_orient_matrix_UB_31      -0.0474021000
_diffrn_orient_matrix_UB_32      -0.1127836000
_diffrn_orient_matrix_UB_33      -0.0265924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4168
_reflns_number_total             4258
_reflns_odcompleteness_completeness 99.95
_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 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0695P)²+0.1373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1040
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(4)
 0.1(4)
2. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C5(H5), B1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9), C11(H11), C17(H17), C19(H19)
3.d Idealised Me refined as rotating group:
 C5AA(H5AA,H5AB,H5AC), C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O -0.0259(3) 0.60902(13) 0.17452(7) 0.0824(5) Uani 1 1 d . . . . .
N1 N 0.60195(17) 0.49890(12) 0.37587(6) 0.0464(3) Uani 1 1 d . . . . .
N2 N 0.50843(18) 0.33376(11) 0.38192(6) 0.0452(3) Uani 1 1 d . . . . .
C1 C 0.46141(19) 0.43875(13) 0.38788(6) 0.0398(3) Uani 1 1 d . . . . .
C2 C 0.7376(2) 0.42956(19) 0.36182(10) 0.0628(5) Uani 1 1 d . . . . .
H2 H 0.848939 0.450756 0.351741 0.075 Uiso 1 1 calc R . . . .
C3 C 0.6786(3) 0.32624(18) 0.36547(10) 0.0610(5) Uani 1 1 d . . . . .
H3 H 0.740466 0.262174 0.358283 0.073 Uiso 1 1 calc R . . . .
C4 C 0.3692(2) 0.25388(14) 0.39154(8) 0.0476(4) Uani 1 1 d . . . . .
H4A H 0.404374 0.197562 0.419652 0.057 Uiso 1 1 calc R . . . .
H4B H 0.336558 0.219047 0.354249 0.057 Uiso 1 1 calc R . . . .
C5 C 0.2192(2) 0.32195(14) 0.41684(8) 0.0486(4) Uani 1 1 d . . . . .
H5 H 0.111367 0.298977 0.397869 0.058 Uiso 1 1 calc R . . . .
C5AA C 0.5475(3) 0.6198(2) 0.26705(9) 0.0693(6) Uani 1 1 d . . . . .
H5AA H 0.652106 0.584073 0.255044 0.104 Uiso 1 1 calc GR . . . .
H5AB H 0.515433 0.673226 0.237530 0.104 Uiso 1 1 calc GR . . . .
H5AC H 0.457478 0.566194 0.270895 0.104 Uiso 1 1 calc GR . . . .
C6 C 0.2075(4) 0.3031(2) 0.48426(10) 0.0802(7) Uani 1 1 d . . . . .
H6A H 0.192853 0.226061 0.492065 0.120 Uiso 1 1 calc GR . . . .
H6B H 0.110912 0.342866 0.500017 0.120 Uiso 1 1 calc GR . . . .
H6C H 0.311322 0.328389 0.503021 0.120 Uiso 1 1 calc GR . . . .
C7 C 0.17108(18) 0.49836(13) 0.33903(7) 0.0406(3) Uani 1 1 d . . . . .
C8 C 0.1549(2) 0.42777(14) 0.29034(7) 0.0455(4) Uani 1 1 d . . . . .
H8 H 0.190475 0.355323 0.295088 0.055 Uiso 1 1 calc R . . . .
C9 C 0.0891(2) 0.45876(14) 0.23516(8) 0.0507(4) Uani 1 1 d . . . . .
H9 H 0.079793 0.408090 0.204241 0.061 Uiso 1 1 calc R . . . .
C10 C 0.0378(3) 0.56635(15) 0.22721(9) 0.0545(4) Uani 1 1 d . . . . .
C11 C 0.0503(3) 0.63909(14) 0.27448(10) 0.0572(4) Uani 1 1 d . . . . .
H11 H 0.014227 0.711308 0.269183 0.069 Uiso 1 1 calc R . . . .
C12 C 0.1151(2) 0.60730(13) 0.32957(8) 0.0474(4) Uani 1 1 d . . . . .
C13 C 0.1216(3) 0.69208(16) 0.37873(10) 0.0645(5) Uani 1 1 d . . . . .
H13A H 0.054084 0.667324 0.412028 0.097 Uiso 1 1 calc GR . . . .
H13B H 0.076113 0.760407 0.364240 0.097 Uiso 1 1 calc GR . . . .
H13C H 0.238785 0.702425 0.391180 0.097 Uiso 1 1 calc GR . . . .
C14 C -0.0593(4) 0.5356(2) 0.12759(11) 0.0804(7) Uani 1 1 d . . . . .
H14A H -0.104727 0.575261 0.094046 0.121 Uiso 1 1 calc GR . . . .
H14B H -0.141625 0.481719 0.140446 0.121 Uiso 1 1 calc GR . . . .
H14C H 0.045647 0.499568 0.116167 0.121 Uiso 1 1 calc GR . . . .
C15 C 0.6052(2) 0.61733(14) 0.37805(8) 0.0461(4) Uani 1 1 d . . . . .
C16 C 0.5748(2) 0.67619(16) 0.32620(8) 0.0523(4) Uani 1 1 d . . . . .
C17 C 0.5668(3) 0.79017(17) 0.33088(10) 0.0625(5) Uani 1 1 d . . . . .
H17 H 0.545201 0.831503 0.296760 0.075 Uiso 1 1 calc R . . . .
C18 C 0.5899(3) 0.84371(17) 0.38474(11) 0.0650(5) Uani 1 1 d . . . . .
C19 C 0.6248(3) 0.78170(18) 0.43493(10) 0.0673(5) Uani 1 1 d . . . . .
H19 H 0.643270 0.817291 0.471127 0.081 Uiso 1 1 calc R . . . .
C20 C 0.6332(3) 0.66736(17) 0.43298(8) 0.0584(5) Uani 1 1 d . . . . .
C21 C 0.6674(5) 0.6013(2) 0.48846(11) 0.0916(9) Uani 1 1 d . . . . .
H21A H 0.568403 0.557014 0.497492 0.137 Uiso 1 1 calc GR . . . .
H21B H 0.690143 0.650026 0.521224 0.137 Uiso 1 1 calc GR . . . .
H21C H 0.765292 0.554600 0.482081 0.137 Uiso 1 1 calc GR . . . .
C22 C 0.5721(4) 0.9669(2) 0.38893(16) 0.0937(9) Uani 1 1 d . . . . .
H22A H 0.613029 0.999957 0.352678 0.141 Uiso 1 1 calc GR . . . .
H22B H 0.638750 0.993483 0.422032 0.141 Uiso 1 1 calc GR . . . .
H22C H 0.453225 0.985719 0.394754 0.141 Uiso 1 1 calc GR . . . .
B1 B 0.2583(2) 0.45376(15) 0.40055(8) 0.0412(4) Uani 1 1 d . . . . .
H1 H 0.235727 0.502543 0.434476 0.049 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.381(2) . ?
O1 C14 1.404(3) . ?
N1 C1 1.341(2) . ?
N1 C2 1.386(2) . ?
N1 C15 1.442(2) . ?
N2 C1 1.336(2) . ?
N2 C3 1.375(2) . ?
N2 C4 1.470(2) . ?
C1 B1 1.613(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.341(3) . ?
C3 H3 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.537(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.530(3) . ?
C5 B1 1.673(2) . ?
C5AA H5AA 0.9600 . ?
C5AA H5AB 0.9600 . ?
C5AA H5AC 0.9600 . ?
C5AA C16 1.507(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.394(2) . ?
C7 C12 1.411(2) . ?
C7 B1 1.628(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(2) . ?
C10 C11 1.383(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(3) . ?
C12 C13 1.510(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.384(2) . ?
C15 C20 1.390(2) . ?
C16 C17 1.393(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(3) . ?
C18 C19 1.381(3) . ?
C18 C22 1.509(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.394(3) . ?
C20 C21 1.503(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
B1 H1 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C14 117.80(16) . . ?
C1 N1 C2 109.36(15) . . ?
C1 N1 C15 123.55(14) . . ?
C2 N1 C15 127.09(15) . . ?
C1 N2 C3 110.68(15) . . ?
C1 N2 C4 114.64(13) . . ?
C3 N2 C4 134.61(15) . . ?
N1 C1 B1 140.27(15) . . ?
N2 C1 N1 106.24(14) . . ?
N2 C1 B1 113.15(13) . . ?
N1 C2 H2 126.4 . . ?
C3 C2 N1 107.30(16) . . ?
C3 C2 H2 126.4 . . ?
N2 C3 H3 126.8 . . ?
C2 C3 N2 106.41(17) . . ?
C2 C3 H3 126.8 . . ?
N2 C4 H4A 110.8 . . ?
N2 C4 H4B 110.8 . . ?
N2 C4 C5 104.76(13) . . ?
H4A C4 H4B 108.9 . . ?
C5 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C4 C5 H5 109.5 . . ?
C4 C5 B1 107.41(13) . . ?
C6 C5 C4 109.14(18) . . ?
C6 C5 H5 109.5 . . ?
C6 C5 B1 111.73(16) . . ?
B1 C5 H5 109.5 . . ?
H5AA C5AA H5AB 109.5 . . ?
H5AA C5AA H5AC 109.5 . . ?
H5AB C5AA H5AC 109.5 . . ?
C16 C5AA H5AA 109.5 . . ?
C16 C5AA H5AB 109.5 . . ?
C16 C5AA H5AC 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 115.72(15) . . ?
C8 C7 B1 119.58(14) . . ?
C12 C7 B1 124.64(14) . . ?
C7 C8 H8 117.9 . . ?
C9 C8 C7 124.15(15) . . ?
C9 C8 H8 117.9 . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.59(16) . . ?
C10 C9 H9 120.7 . . ?
O1 C10 C11 115.99(16) . . ?
C9 C10 O1 124.78(17) . . ?
C9 C10 C11 119.23(16) . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.82(16) . . ?
C12 C11 H11 119.1 . . ?
C7 C12 C13 121.49(16) . . ?
C11 C12 C7 120.48(15) . . ?
C11 C12 C13 118.02(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N1 119.06(16) . . ?
C16 C15 C20 122.83(17) . . ?
C20 C15 N1 118.07(16) . . ?
C15 C16 C5AA 121.70(18) . . ?
C15 C16 C17 117.39(18) . . ?
C17 C16 C5AA 120.90(19) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 121.96(19) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 C22 120.7(2) . . ?
C19 C18 C17 118.55(19) . . ?
C19 C18 C22 120.7(2) . . ?
C18 C19 H19 119.0 . . ?
C18 C19 C20 121.97(19) . . ?
C20 C19 H19 119.0 . . ?
C15 C20 C19 117.25(18) . . ?
C15 C20 C21 121.64(19) . . ?
C19 C20 C21 121.10(19) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 B1 C5 96.14(12) . . ?
C1 B1 C7 107.20(12) . . ?
C1 B1 H1 112.3 . . ?
C5 B1 H1 112.3 . . ?
C7 B1 C5 115.40(14) . . ?
C7 B1 H1 112.3 . . ?

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
O1 C10 C11 C12 -178.8(2) . . . . ?
N1 C1 B1 C5 -174.21(19) . . . . ?
N1 C1 B1 C7 66.8(2) . . . . ?
N1 C2 C3 N2 -0.3(2) . . . . ?
N1 C15 C16 C5AA -3.2(3) . . . . ?
N1 C15 C16 C17 175.53(16) . . . . ?
N1 C15 C20 C19 -175.94(18) . . . . ?
N1 C15 C20 C21 2.7(3) . . . . ?
N2 C1 B1 C5 13.70(16) . . . . ?
N2 C1 B1 C7 -105.31(15) . . . . ?
N2 C4 C5 C6 -102.92(18) . . . . ?
N2 C4 C5 B1 18.38(18) . . . . ?
C1 N1 C2 C3 -0.1(2) . . . . ?
C1 N1 C15 C16 -93.4(2) . . . . ?
C1 N1 C15 C20 84.5(2) . . . . ?
C1 N2 C3 C2 0.6(2) . . . . ?
C1 N2 C4 C5 -9.95(18) . . . . ?
C2 N1 C1 N2 0.4(2) . . . . ?
C2 N1 C1 B1 -172.0(2) . . . . ?
C2 N1 C15 C16 86.8(2) . . . . ?
C2 N1 C15 C20 -95.3(2) . . . . ?
C3 N2 C1 N1 -0.64(19) . . . . ?
C3 N2 C1 B1 174.10(15) . . . . ?
C3 N2 C4 C5 173.3(2) . . . . ?
C4 N2 C1 N1 -178.17(13) . . . . ?
C4 N2 C1 B1 -3.43(19) . . . . ?
C4 N2 C3 C2 177.43(19) . . . . ?
C4 C5 B1 C1 -18.73(16) . . . . ?
C4 C5 B1 C7 93.63(16) . . . . ?
C5AA C16 C17 C18 179.42(19) . . . . ?
C6 C5 B1 C1 100.94(19) . . . . ?
C6 C5 B1 C7 -146.71(18) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C8 C7 C12 C11 -0.6(2) . . . . ?
C8 C7 C12 C13 178.75(17) . . . . ?
C8 C7 B1 C1 71.38(18) . . . . ?
C8 C7 B1 C5 -34.3(2) . . . . ?
C8 C9 C10 O1 178.4(2) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C7 0.1(3) . . . . ?
C10 C11 C12 C13 -179.2(2) . . . . ?
C12 C7 C8 C9 0.1(2) . . . . ?
C12 C7 B1 C1 -105.75(17) . . . . ?
C12 C7 B1 C5 148.53(15) . . . . ?
C14 O1 C10 C9 7.6(4) . . . . ?
C14 O1 C10 C11 -172.8(2) . . . . ?
C15 N1 C1 N2 -179.33(15) . . . . ?
C15 N1 C1 B1 8.2(3) . . . . ?
C15 N1 C2 C3 179.68(18) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C15 C20 C19 1.9(3) . . . . ?
C16 C15 C20 C21 -179.5(2) . . . . ?
C16 C17 C18 C19 1.1(3) . . . . ?
C16 C17 C18 C22 -177.1(2) . . . . ?
C17 C18 C19 C20 -1.5(3) . . . . ?
C18 C19 C20 C15 0.1(3) . . . . ?
C18 C19 C20 C21 -178.6(2) . . . . ?
C20 C15 C16 C5AA 179.04(19) . . . . ?
C20 C15 C16 C17 -2.3(3) . . . . ?
C22 C18 C19 C20 176.7(2) . . . . ?
B1 C7 C8 C9 -177.26(16) . . . . ?
B1 C7 C12 C11 176.67(16) . . . . ?
B1 C7 C12 C13 -4.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.574
_oxdiff_exptl_absorpt_empirical_full_min 0.665
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(4)
2 0.1(4)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/pentane'
_chemical_properties_physical    Moisture-sensitive
