# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_dk44_2(1)
_database_code_depnum_ccdc_archive 'CCDC 2040729'
loop_
_audit_author_name
_audit_author_address
'Tilo Soehnel'
;University of Auckland
New Zealand
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-12-13 downloaded from the CCDC.
;
_audit_creation_date             2020-10-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 B N2 O5'
_chemical_formula_sum            'C21 H21 B N2 O5'
_chemical_formula_weight         392.21
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H21BN2O5
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                   6.6897(2)
_cell_length_b                   6.8564(2)
_cell_length_c                   39.6011(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1816.39(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4829
_cell_measurement_temperature    105(8)
_cell_measurement_theta_max      73.8040
_cell_measurement_theta_min      6.5050
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89990
_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            ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            9162
_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         67.737
_diffrn_reflns_theta_min         6.552
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      105(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  12.00   0.50    1.27    --  -47.48  51.00  58.00  150
  2  ω     28.00  75.00   0.50    1.27    --   47.48  57.00 150.00   94
  3  ω     40.00 122.00   0.50    5.08    --  102.39 -30.00 120.00  164
  4  ω     82.00 112.00   0.50    5.08    --  102.39  30.00   0.00   60
  5  ω     80.00 172.00   0.50    5.08    --  102.39  83.00 -87.00  184
  6  ω    147.00 174.00   0.50    5.08    --  102.39 111.00 -60.00   54
  7  ω    146.00 171.00   0.50    5.08    --  102.39 111.00 -30.00   50
  8  ω    109.00 138.00   0.50    5.08    --  102.39 111.00 -60.00   58
  9  ω    112.00 145.00   0.50    5.08    --  102.39 178.00-180.00   66
 10  ω     62.00 110.00   0.50    5.08    --  102.39 178.00-180.00   96
 11  ω    -84.00 -44.00   0.50    5.08    --  -90.25 111.00 -60.00   80
 12  ω   -105.00 -29.00   0.50    5.08    --  -90.25  51.00  58.00  152
 13  ω   -122.00 -97.00   0.50    5.08    --  -90.25 -92.00  51.00   50
 14  ω   -123.00 -83.00   0.50    1.27    --  -47.48-125.00-180.00   80
 15  ω     46.00  97.00   0.50    1.27    --   47.48-125.00   0.00  102
 16  ω     59.00 109.00   0.50    5.08    --  102.39 -95.00 -30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1712662000
_diffrn_orient_matrix_UB_12      -0.1361189000
_diffrn_orient_matrix_UB_13      0.0110275000
_diffrn_orient_matrix_UB_21      0.1050043000
_diffrn_orient_matrix_UB_22      0.0338359000
_diffrn_orient_matrix_UB_23      -0.0341011000
_diffrn_orient_matrix_UB_31      0.1124630000
_diffrn_orient_matrix_UB_32      0.1756161000
_diffrn_orient_matrix_UB_33      0.0151246000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3058
_reflns_number_total             3280
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.62
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1168 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.033
_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)+(0.0325P)²+0.6064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0782
_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 Ternary CH refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.3438(4) 0.0843(4) 0.52965(6) 0.0215(5) Uani 1 1 d . . . . .
H1 H 0.332893 0.217602 0.525724 0.026 Uiso 1 1 calc R U . . .
C2 C 0.3442(4) -0.0432(4) 0.50264(7) 0.0234(6) Uani 1 1 d . . . . .
H2 H 0.335490 0.005862 0.480794 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3576(4) -0.2452(4) 0.50754(6) 0.0214(5) Uani 1 1 d . . . . .
C4 C 0.3581(4) -0.3822(4) 0.47783(7) 0.0265(6) Uani 1 1 d . . . . .
H4A H 0.394321 -0.510728 0.485269 0.040 Uiso 1 1 calc R U . . .
H4B H 0.453162 -0.337689 0.461379 0.040 Uiso 1 1 calc R U . . .
H4C H 0.227298 -0.385641 0.467891 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3711(4) -0.3121(4) 0.54061(6) 0.0224(5) Uani 1 1 d . . . . .
H5 H 0.379333 -0.445628 0.544498 0.027 Uiso 1 1 calc R U . . .
C6 C 0.3728(4) -0.1859(3) 0.56800(7) 0.0206(5) Uani 1 1 d . . . . .
H6 H 0.382665 -0.235134 0.589820 0.025 Uiso 1 1 calc R U . . .
C7 C 0.3595(4) 0.0159(3) 0.56275(6) 0.0180(5) Uani 1 1 d . . . . .
C8 C 0.3674(4) 0.1524(3) 0.59183(6) 0.0168(5) Uani 1 1 d . . . . .
C9 C 0.5265(4) 0.1428(3) 0.61418(6) 0.0169(5) Uani 1 1 d . . . . .
C10 C 0.6957(4) 0.0179(4) 0.61576(6) 0.0205(5) Uani 1 1 d . . . . .
H10 H 0.728059 -0.079535 0.600375 0.025 Uiso 1 1 calc R U . . .
C11 C 0.8029(4) 0.0670(4) 0.64409(6) 0.0229(6) Uani 1 1 d . . . . .
H11 H 0.920247 0.008784 0.651624 0.027 Uiso 1 1 calc R U . . .
C12 C 0.7004(4) 0.2223(4) 0.65947(6) 0.0207(5) Uani 1 1 d . . . . .
H12 H 0.741213 0.284550 0.679165 0.025 Uiso 1 1 calc R U . . .
C13 C 0.2126(4) 0.2891(4) 0.59689(6) 0.0182(5) Uani 1 1 d . . . . .
C14 C 0.0352(4) 0.3225(4) 0.57888(6) 0.0220(6) Uani 1 1 d . . . . .
H14 H -0.006442 0.257109 0.559543 0.026 Uiso 1 1 calc R U . . .
C15 C -0.0665(4) 0.4710(4) 0.59528(7) 0.0236(6) Uani 1 1 d . . . . .
H15 H -0.188596 0.524555 0.588967 0.028 Uiso 1 1 calc R U . . .
C16 C 0.0493(4) 0.5248(4) 0.62304(6) 0.0216(5) Uani 1 1 d . . . . .
H16 H 0.015205 0.621215 0.638527 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4523(4) 0.7027(3) 0.68641(6) 0.0188(5) Uani 1 1 d . . . . .
H17 H 0.583314 0.728200 0.696556 0.023 Uiso 1 1 calc R U . . .
C18 C 0.3296(4) 0.5547(3) 0.70727(6) 0.0188(5) Uani 1 1 d . . . . .
H18 H 0.398011 0.520111 0.728314 0.023 Uiso 1 1 calc R U . . .
C19 C 0.3227(4) 0.8867(3) 0.68515(6) 0.0199(5) Uani 1 1 d . . . . .
H19 H 0.329954 0.945334 0.662611 0.024 Uiso 1 1 calc R U . . .
C21 C 0.1295(4) 0.6552(3) 0.71414(6) 0.0201(5) Uani 1 1 d . . . . .
H21 H 0.022274 0.565922 0.707389 0.024 Uiso 1 1 calc R U . . .
C22 C 0.0932(4) 0.7151(4) 0.75053(7) 0.0233(6) Uani 1 1 d . . . . .
H22A H -0.035463 0.779803 0.751936 0.028 Uiso 1 1 calc R U . . .
H22B H 0.086364 0.598515 0.764354 0.028 Uiso 1 1 calc R U . . .
B B 0.3822(4) 0.4299(4) 0.65220(7) 0.0177(6) Uani 1 1 d . . . . .
N1 N 0.2175(3) 0.4172(3) 0.62421(5) 0.0189(5) Uani 1 1 d . . . . .
N2 N 0.5370(3) 0.2683(3) 0.64198(5) 0.0174(4) Uani 1 1 d . . . . .
O1 O 0.4696(3) 0.6213(2) 0.65346(4) 0.0206(4) Uani 1 1 d . . . . .
O2 O 0.3048(3) 0.3880(2) 0.68573(4) 0.0197(4) Uani 1 1 d . . . . .
O3 O 0.1246(3) 0.8230(2) 0.69171(4) 0.0214(4) Uani 1 1 d . . . . .
O4 O 0.3895(3) 1.0216(3) 0.70954(5) 0.0246(4) Uani 1 1 d . . . . .
O5 O 0.2412(3) 0.8407(3) 0.76407(5) 0.0261(4) Uani 1 1 d . . . . .
H5A H 0.284(5) 0.933(5) 0.7449(9) 0.045(10) Uiso 1 1 d . . . . .
H4 H 0.364(7) 1.137(7) 0.7017(12) 0.079(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.382(4) . ?
C1 C7 1.396(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.401(4) . ?
C3 C4 1.506(3) . ?
C3 C5 1.391(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C6 1.387(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.402(3) . ?
C7 C8 1.485(3) . ?
C8 C9 1.386(4) . ?
C8 C13 1.411(4) . ?
C9 C10 1.420(4) . ?
C9 N2 1.399(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.405(4) . ?
C12 H12 0.9300 . ?
C12 N2 1.332(3) . ?
C13 C14 1.404(4) . ?
C13 N1 1.394(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.395(4) . ?
C16 H16 0.9300 . ?
C16 N1 1.346(3) . ?
C17 H17 0.9800 . ?
C17 C18 1.544(3) . ?
C17 C19 1.532(3) . ?
C17 O1 1.424(3) . ?
C18 H18 0.9800 . ?
C18 C21 1.530(4) . ?
C18 O2 1.436(3) . ?
C19 H19 0.9800 . ?
C19 O3 1.419(3) . ?
C19 O4 1.410(3) . ?
C21 H21 0.9800 . ?
C21 C22 1.518(4) . ?
C21 O3 1.454(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 O5 1.417(3) . ?
B N1 1.565(4) . ?
B N2 1.570(3) . ?
B O1 1.438(3) . ?
B O2 1.454(3) . ?
O4 H4 0.86(5) . ?
O5 H5A 1.03(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.5 . . ?
C2 C1 C7 120.9(2) . . ?
C7 C1 H1 119.5 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 120.6(2) . . ?
C5 C3 C2 117.4(2) . . ?
C5 C3 C4 122.0(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5 119.0 . . ?
C6 C5 C3 122.1(2) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.9(2) . . ?
C7 C6 H6 120.0 . . ?
C1 C7 C6 118.4(2) . . ?
C1 C7 C8 121.3(2) . . ?
C6 C7 C8 120.3(2) . . ?
C9 C8 C7 119.5(2) . . ?
C9 C8 C13 120.3(2) . . ?
C13 C8 C7 120.2(2) . . ?
C8 C9 C10 132.0(2) . . ?
C8 C9 N2 120.8(2) . . ?
N2 C9 C10 107.2(2) . . ?
C9 C10 H10 126.1 . . ?
C11 C10 C9 107.7(2) . . ?
C11 C10 H10 126.1 . . ?
C10 C11 H11 126.7 . . ?
C10 C11 C12 106.6(2) . . ?
C12 C11 H11 126.7 . . ?
C11 C12 H12 124.6 . . ?
N2 C12 C11 110.7(2) . . ?
N2 C12 H12 124.6 . . ?
C14 C13 C8 131.1(2) . . ?
N1 C13 C8 120.8(2) . . ?
N1 C13 C14 108.1(2) . . ?
C13 C14 H14 126.4 . . ?
C15 C14 C13 107.3(2) . . ?
C15 C14 H14 126.4 . . ?
C14 C15 H15 126.5 . . ?
C14 C15 C16 106.9(2) . . ?
C16 C15 H15 126.5 . . ?
C15 C16 H16 124.9 . . ?
N1 C16 C15 110.3(2) . . ?
N1 C16 H16 124.9 . . ?
C18 C17 H17 111.9 . . ?
C19 C17 H17 111.9 . . ?
C19 C17 C18 104.9(2) . . ?
O1 C17 H17 111.9 . . ?
O1 C17 C18 106.01(19) . . ?
O1 C17 C19 109.81(19) . . ?
C17 C18 H18 111.5 . . ?
C21 C18 C17 105.33(19) . . ?
C21 C18 H18 111.5 . . ?
O2 C18 C17 105.48(19) . . ?
O2 C18 H18 111.5 . . ?
O2 C18 C21 111.3(2) . . ?
C17 C19 H19 109.8 . . ?
O3 C19 C17 105.61(19) . . ?
O3 C19 H19 109.8 . . ?
O4 C19 C17 109.8(2) . . ?
O4 C19 H19 109.8 . . ?
O4 C19 O3 111.9(2) . . ?
C18 C21 H21 108.1 . . ?
C22 C21 C18 115.5(2) . . ?
C22 C21 H21 108.1 . . ?
O3 C21 C18 105.5(2) . . ?
O3 C21 H21 108.1 . . ?
O3 C21 C22 111.2(2) . . ?
C21 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
O5 C22 C21 114.3(2) . . ?
O5 C22 H22A 108.7 . . ?
O5 C22 H22B 108.7 . . ?
N1 B N2 104.04(18) . . ?
O1 B N1 111.2(2) . . ?
O1 B N2 112.7(2) . . ?
O1 B O2 107.1(2) . . ?
O2 B N1 112.7(2) . . ?
O2 B N2 109.30(19) . . ?
C13 N1 B 127.0(2) . . ?
C16 N1 C13 107.4(2) . . ?
C16 N1 B 125.6(2) . . ?
C9 N2 B 127.2(2) . . ?
C12 N2 C9 107.7(2) . . ?
C12 N2 B 125.1(2) . . ?
C17 O1 B 110.90(19) . . ?
C18 O2 B 110.11(18) . . ?
C19 O3 C21 109.53(19) . . ?
C19 O4 H4 107(3) . . ?
C22 O5 H5A 107(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
C1 C2 C3 C4 -179.9(2) . . . . ?
C1 C2 C3 C5 -0.2(4) . . . . ?
C1 C7 C8 C9 -124.2(3) . . . . ?
C1 C7 C8 C13 56.6(3) . . . . ?
C2 C1 C7 C6 -0.9(4) . . . . ?
C2 C1 C7 C8 177.5(2) . . . . ?
C2 C3 C5 C6 -0.4(4) . . . . ?
C3 C5 C6 C7 0.3(4) . . . . ?
C4 C3 C5 C6 179.3(3) . . . . ?
C5 C6 C7 C1 0.3(4) . . . . ?
C5 C6 C7 C8 -178.1(2) . . . . ?
C6 C7 C8 C9 54.3(3) . . . . ?
C6 C7 C8 C13 -124.9(3) . . . . ?
C7 C1 C2 C3 0.9(4) . . . . ?
C7 C8 C9 C10 -1.5(4) . . . . ?
C7 C8 C9 N2 -179.4(2) . . . . ?
C7 C8 C13 C14 1.7(4) . . . . ?
C7 C8 C13 N1 179.6(2) . . . . ?
C8 C9 C10 C11 -177.5(3) . . . . ?
C8 C9 N2 C12 178.0(2) . . . . ?
C8 C9 N2 B 0.1(4) . . . . ?
C8 C13 C14 C15 178.2(3) . . . . ?
C8 C13 N1 C16 -178.2(2) . . . . ?
C8 C13 N1 B -0.6(4) . . . . ?
C9 C8 C13 C14 -177.5(3) . . . . ?
C9 C8 C13 N1 0.4(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C9 N2 C12 -0.4(3) . . . . ?
C10 C9 N2 B -178.2(2) . . . . ?
C10 C11 C12 N2 0.4(3) . . . . ?
C11 C12 N2 C9 0.0(3) . . . . ?
C11 C12 N2 B 177.9(2) . . . . ?
C13 C8 C9 C10 177.7(3) . . . . ?
C13 C8 C9 N2 -0.2(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C13 N1 C16 0.1(3) . . . . ?
C14 C13 N1 B 177.7(2) . . . . ?
C14 C15 C16 N1 0.5(3) . . . . ?
C15 C16 N1 C13 -0.4(3) . . . . ?
C15 C16 N1 B -178.0(2) . . . . ?
C17 C18 C21 C22 -110.2(2) . . . . ?
C17 C18 C21 O3 13.0(2) . . . . ?
C17 C18 O2 B -6.4(3) . . . . ?
C17 C19 O3 C21 31.4(2) . . . . ?
C18 C17 C19 O3 -21.5(2) . . . . ?
C18 C17 C19 O4 99.2(2) . . . . ?
C18 C17 O1 B -4.2(3) . . . . ?
C18 C21 C22 O5 57.0(3) . . . . ?
C18 C21 O3 C19 -28.2(2) . . . . ?
C19 C17 C18 C21 4.8(2) . . . . ?
C19 C17 C18 O2 122.6(2) . . . . ?
C19 C17 O1 B -117.0(2) . . . . ?
C21 C18 O2 B 107.3(2) . . . . ?
C22 C21 O3 C19 97.8(2) . . . . ?
N1 C13 C14 C15 0.2(3) . . . . ?
N1 B N2 C9 -0.2(3) . . . . ?
N1 B N2 C12 -177.7(2) . . . . ?
N1 B O1 C17 123.8(2) . . . . ?
N1 B O2 C18 -118.5(2) . . . . ?
N2 C9 C10 C11 0.6(3) . . . . ?
N2 B N1 C13 0.4(3) . . . . ?
N2 B N1 C16 177.7(2) . . . . ?
N2 B O1 C17 -119.8(2) . . . . ?
N2 B O2 C18 126.3(2) . . . . ?
O1 C17 C18 C21 -111.4(2) . . . . ?
O1 C17 C18 O2 6.4(3) . . . . ?
O1 C17 C19 O3 92.0(2) . . . . ?
O1 C17 C19 O4 -147.2(2) . . . . ?
O1 B N1 C13 122.0(2) . . . . ?
O1 B N1 C16 -60.8(3) . . . . ?
O1 B N2 C9 -120.8(2) . . . . ?
O1 B N2 C12 61.8(3) . . . . ?
O1 B O2 C18 4.0(3) . . . . ?
O2 C18 C21 C22 136.0(2) . . . . ?
O2 C18 C21 O3 -100.8(2) . . . . ?
O2 B N1 C13 -117.8(3) . . . . ?
O2 B N1 C16 59.4(3) . . . . ?
O2 B N2 C9 120.3(2) . . . . ?
O2 B N2 C12 -57.1(3) . . . . ?
O2 B O1 C17 0.3(3) . . . . ?
O3 C21 C22 O5 -63.2(3) . . . . ?
O4 C19 O3 C21 -88.0(2) . . . . ?

_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 1.475
_oxdiff_exptl_absorpt_empirical_full_min 0.794
####################################################################### 
# 
# 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_mh031
_database_code_depnum_ccdc_archive 'CCDC 2040730'
loop_
_audit_author_name
_audit_author_address
'Tilo Soehnel'
;University of Auckland
New Zealand
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-12-13 downloaded from the CCDC.
;
_audit_creation_date             2020-10-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 B N2 O2'
_chemical_formula_sum            'C20 H23 B N2 O2'
_chemical_formula_weight         334.21
_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'
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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   11.8127(2)
_cell_length_b                   8.27160(10)
_cell_length_c                   38.1140(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3724.12(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10705
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.9040
_cell_measurement_theta_min      4.4350
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            18535
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         5.967
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00 -28.00   0.50    0.67    --  -47.48 -73.00 -83.00   66
  2  ω   -122.00 -71.00   0.50    0.67    --  -47.48 -73.00 -83.00  102
  3  ω    -84.00 -13.00   0.50    2.69    --  -90.25 120.00 117.00  142
  4  ω   -103.00 -74.00   0.50    2.69    --  -90.25 -48.00 101.00   58
  5  ω     96.00 160.00   0.50    2.69    --  101.53 120.00 117.00  128
  6  ω   -124.00 -71.00   0.50    0.67    --  -47.48-125.00-180.00  106
  7  ω     31.00  97.00   0.50    0.67    --   47.48-125.00 -90.00  132
  8  ω   -114.00 -15.00   0.50    2.69    --  -90.25  73.00  45.00  198
  9  ω    117.00 144.00   0.50    2.69    --  101.53 178.00  30.00   54
 10  ω     81.00 178.00   0.50    2.69    --  101.53  30.00-120.00  194
 11  ω     73.00 148.00   0.50    2.69    --  101.53 178.00-150.00  150
 12  ω    138.00 174.00   0.50    2.69    --  101.53  30.00   0.00   72
 13  ω     85.00 125.00   0.50    2.69    --  101.53  30.00   0.00   80
 14  ω     68.00 109.00   0.50    2.69    --  101.53 178.00  30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0313614000
_diffrn_orient_matrix_UB_12      0.1434515000
_diffrn_orient_matrix_UB_13      -0.0238606000
_diffrn_orient_matrix_UB_21      0.1256588000
_diffrn_orient_matrix_UB_22      -0.0493057000
_diffrn_orient_matrix_UB_23      0.0019197000
_diffrn_orient_matrix_UB_31      -0.0156992000
_diffrn_orient_matrix_UB_32      -0.1080607000
_diffrn_orient_matrix_UB_33      -0.0325533000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3078
_reflns_number_total             3395
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.00074(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.038
_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)+(0.0448P)²+1.5097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0966
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C20(H20A,H20B,H20C),
 C21(H21A,H21B,H21C)
;
_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 0.63099(7) 0.78794(11) 0.28531(2) 0.0270(2) Uani 1 1 d . . . . .
O2 O 0.44347(7) 0.85457(11) 0.28614(2) 0.0267(2) Uani 1 1 d . . . . .
N1 N 0.54115(9) 0.83545(12) 0.34392(3) 0.0218(2) Uani 1 1 d . . . . .
N2 N 0.49665(9) 0.58506(12) 0.31075(2) 0.0209(2) Uani 1 1 d . . . . .
C1 C 0.35485(18) 0.2726(2) 0.50387(4) 0.0530(5) Uani 1 1 d . . . . .
H1A H 0.365047 0.345089 0.523281 0.079 Uiso 1 1 calc R U . . .
H1B H 0.401809 0.179025 0.507061 0.079 Uiso 1 1 calc R U . . .
H1C H 0.276960 0.239974 0.502641 0.079 Uiso 1 1 calc R U . . .
C2 C 0.38750(14) 0.35715(18) 0.47020(3) 0.0349(3) Uani 1 1 d . . . . .
C3 C 0.30664(12) 0.43565(17) 0.45009(3) 0.0311(3) Uani 1 1 d . . . . .
H3 H 0.231924 0.437052 0.457784 0.037 Uiso 1 1 calc R U . . .
C4 C 0.33407(11) 0.51256(15) 0.41868(3) 0.0244(3) Uani 1 1 d . . . . .
C5 C 0.44720(11) 0.51121(14) 0.40761(3) 0.0206(3) Uani 1 1 d . . . . .
C6 C 0.53113(11) 0.43476(15) 0.42762(3) 0.0250(3) Uani 1 1 d . . . . .
C7 C 0.49910(13) 0.35831(17) 0.45868(3) 0.0327(3) Uani 1 1 d . . . . .
H7 H 0.554034 0.306583 0.472079 0.039 Uiso 1 1 calc R U . . .
C8 C 0.24346(12) 0.59181(17) 0.39693(4) 0.0304(3) Uani 1 1 d . . . . .
H8A H 0.270052 0.694742 0.388716 0.046 Uiso 1 1 calc R U . . .
H8B H 0.176849 0.607076 0.410973 0.046 Uiso 1 1 calc R U . . .
H8C H 0.225645 0.524182 0.377218 0.046 Uiso 1 1 calc R U . . .
C9 C 0.65294(12) 0.43560(17) 0.41595(4) 0.0311(3) Uani 1 1 d . . . . .
H9A H 0.658312 0.390928 0.392766 0.047 Uiso 1 1 calc R U . . .
H9B H 0.697370 0.371774 0.431855 0.047 Uiso 1 1 calc R U . . .
H9C H 0.680767 0.544642 0.415798 0.047 Uiso 1 1 calc R U . . .
C10 C 0.47808(10) 0.59287(14) 0.37402(3) 0.0195(3) Uani 1 1 d . . . . .
C11 C 0.47114(10) 0.51028(15) 0.34273(3) 0.0193(3) Uani 1 1 d . . . . .
C12 C 0.44172(10) 0.34673(15) 0.33550(3) 0.0220(3) Uani 1 1 d . . . . .
H12 H 0.420538 0.268966 0.351854 0.026 Uiso 1 1 calc R U . . .
C13 C 0.45040(11) 0.32523(16) 0.29999(3) 0.0254(3) Uani 1 1 d . . . . .
H13 H 0.436988 0.230070 0.287679 0.030 Uiso 1 1 calc R U . . .
C14 C 0.48364(11) 0.47541(16) 0.28564(3) 0.0248(3) Uani 1 1 d . . . . .
H14 H 0.494871 0.494787 0.261863 0.030 Uiso 1 1 calc R U . . .
C15 C 0.51337(10) 0.75541(15) 0.37465(3) 0.0206(3) Uani 1 1 d . . . . .
C16 C 0.52853(11) 0.86223(15) 0.40282(3) 0.0246(3) Uani 1 1 d . . . . .
H16 H 0.515995 0.839753 0.426405 0.029 Uiso 1 1 calc R U . . .
C17 C 0.56564(11) 1.00732(16) 0.38892(4) 0.0287(3) Uani 1 1 d . . . . .
H17 H 0.582825 1.100907 0.401351 0.034 Uiso 1 1 calc R U . . .
C18 C 0.57231(11) 0.98620(15) 0.35271(4) 0.0269(3) Uani 1 1 d . . . . .
H18 H 0.595105 1.065310 0.336879 0.032 Uiso 1 1 calc R U . . .
B1 B 0.52935(12) 0.77004(18) 0.30490(4) 0.0226(3) Uani 1 1 d . . . . .
C20 C 0.73065(11) 0.71464(18) 0.29812(4) 0.0335(3) Uani 1 1 d . . . . .
H20A H 0.792278 0.737387 0.282455 0.050 Uiso 1 1 calc R U . . .
H20B H 0.719707 0.599848 0.299628 0.050 Uiso 1 1 calc R U . . .
H20C H 0.747768 0.756818 0.320974 0.050 Uiso 1 1 calc R U . . .
C21 C 0.33094(11) 0.85057(18) 0.29862(4) 0.0305(3) Uani 1 1 d . . . . .
H21A H 0.282824 0.908877 0.282753 0.046 Uiso 1 1 calc R U . . .
H21B H 0.327629 0.899723 0.321418 0.046 Uiso 1 1 calc R U . . .
H21C H 0.305886 0.740404 0.300184 0.046 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.4217(16) . ?
O1 C20 1.4113(16) . ?
O2 B1 1.4245(16) . ?
O2 C21 1.4121(15) . ?
N1 C15 1.3848(15) . ?
N1 C18 1.3426(17) . ?
N1 B1 1.5886(17) . ?
N2 C11 1.3997(15) . ?
N2 C14 1.3274(16) . ?
N2 B1 1.5937(18) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.5113(19) . ?
C2 C3 1.386(2) . ?
C2 C7 1.390(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.3942(18) . ?
C4 C5 1.4014(18) . ?
C4 C8 1.5042(19) . ?
C5 C6 1.4017(18) . ?
C5 C10 1.4927(16) . ?
C6 C7 1.3944(18) . ?
C6 C9 1.5061(19) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.3767(17) . ?
C10 C15 1.4078(17) . ?
C11 C12 1.4238(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.3688(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.4129(19) . ?
C14 H14 0.9300 . ?
C15 C16 1.4019(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.3830(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.393(2) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C20 O1 B1 118.56(10) . . ?
C21 O2 B1 119.33(10) . . ?
C15 N1 B1 127.45(10) . . ?
C18 N1 C15 107.33(10) . . ?
C18 N1 B1 125.03(10) . . ?
C11 N2 B1 126.75(10) . . ?
C14 N2 C11 107.51(10) . . ?
C14 N2 B1 125.67(10) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.69(15) . . ?
C3 C2 C7 118.41(12) . . ?
C7 C2 C1 120.90(15) . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 121.90(13) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 118.47(12) . . ?
C3 C4 C8 120.45(12) . . ?
C5 C4 C8 121.07(11) . . ?
C4 C5 C6 120.94(11) . . ?
C4 C5 C10 119.19(11) . . ?
C6 C5 C10 119.87(11) . . ?
C5 C6 C9 120.85(11) . . ?
C7 C6 C5 118.34(13) . . ?
C7 C6 C9 120.80(12) . . ?
C2 C7 C6 121.93(13) . . ?
C2 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C5 120.25(11) . . ?
C11 C10 C15 120.41(11) . . ?
C15 C10 C5 119.34(10) . . ?
N2 C11 C12 107.69(10) . . ?
C10 C11 N2 121.48(11) . . ?
C10 C11 C12 130.83(11) . . ?
C11 C12 H12 126.4 . . ?
C13 C12 C11 107.26(11) . . ?
C13 C12 H12 126.4 . . ?
C12 C13 H13 126.6 . . ?
C12 C13 C14 106.81(11) . . ?
C14 C13 H13 126.6 . . ?
N2 C14 C13 110.73(11) . . ?
N2 C14 H14 124.6 . . ?
C13 C14 H14 124.6 . . ?
N1 C15 C10 120.82(11) . . ?
N1 C15 C16 108.43(11) . . ?
C16 C15 C10 130.75(11) . . ?
C15 C16 H16 126.4 . . ?
C17 C16 C15 107.11(11) . . ?
C17 C16 H16 126.4 . . ?
C16 C17 H17 126.6 . . ?
C16 C17 C18 106.76(11) . . ?
C18 C17 H17 126.6 . . ?
N1 C18 C17 110.37(11) . . ?
N1 C18 H18 124.8 . . ?
C17 C18 H18 124.8 . . ?
O1 B1 O2 106.66(10) . . ?
O1 B1 N1 112.46(11) . . ?
O1 B1 N2 112.22(10) . . ?
O2 B1 N1 111.42(10) . . ?
O2 B1 N2 111.65(11) . . ?
N1 B1 N2 102.55(9) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
N1 C15 C16 C17 0.00(14) . . . . ?
N2 C11 C12 C13 0.37(13) . . . . ?
C1 C2 C3 C4 -179.04(13) . . . . ?
C1 C2 C7 C6 179.65(13) . . . . ?
C2 C3 C4 C5 -0.76(19) . . . . ?
C2 C3 C4 C8 177.95(12) . . . . ?
C3 C2 C7 C6 -0.4(2) . . . . ?
C3 C4 C5 C6 -0.15(18) . . . . ?
C3 C4 C5 C10 179.96(11) . . . . ?
C4 C5 C6 C7 0.72(18) . . . . ?
C4 C5 C6 C9 -179.07(11) . . . . ?
C4 C5 C10 C11 -87.13(15) . . . . ?
C4 C5 C10 C15 92.31(14) . . . . ?
C5 C6 C7 C2 -0.4(2) . . . . ?
C5 C10 C11 N2 178.27(11) . . . . ?
C5 C10 C11 C12 -2.8(2) . . . . ?
C5 C10 C15 N1 -179.11(11) . . . . ?
C5 C10 C15 C16 1.7(2) . . . . ?
C6 C5 C10 C11 92.97(14) . . . . ?
C6 C5 C10 C15 -87.58(14) . . . . ?
C7 C2 C3 C4 1.0(2) . . . . ?
C8 C4 C5 C6 -178.85(11) . . . . ?
C8 C4 C5 C10 1.25(17) . . . . ?
C9 C6 C7 C2 179.36(13) . . . . ?
C10 C5 C6 C7 -179.38(11) . . . . ?
C10 C5 C6 C9 0.82(18) . . . . ?
C10 C11 C12 C13 -178.68(13) . . . . ?
C10 C15 C16 C17 179.31(13) . . . . ?
C11 N2 C14 C13 -0.53(14) . . . . ?
C11 N2 B1 O1 128.22(12) . . . . ?
C11 N2 B1 O2 -112.08(13) . . . . ?
C11 N2 B1 N1 7.31(15) . . . . ?
C11 C10 C15 N1 0.33(18) . . . . ?
C11 C10 C15 C16 -178.90(12) . . . . ?
C11 C12 C13 C14 -0.67(14) . . . . ?
C12 C13 C14 N2 0.77(15) . . . . ?
C14 N2 C11 C10 179.26(11) . . . . ?
C14 N2 C11 C12 0.10(13) . . . . ?
C14 N2 B1 O1 -55.10(16) . . . . ?
C14 N2 B1 O2 64.59(15) . . . . ?
C14 N2 B1 N1 -176.02(11) . . . . ?
C15 N1 C18 C17 0.03(14) . . . . ?
C15 N1 B1 O1 -129.01(12) . . . . ?
C15 N1 B1 O2 111.29(13) . . . . ?
C15 N1 B1 N2 -8.26(15) . . . . ?
C15 C10 C11 N2 -1.17(18) . . . . ?
C15 C10 C11 C12 177.77(12) . . . . ?
C15 C16 C17 C18 0.02(15) . . . . ?
C16 C17 C18 N1 -0.03(15) . . . . ?
C18 N1 C15 C10 -179.41(11) . . . . ?
C18 N1 C15 C16 -0.02(14) . . . . ?
C18 N1 B1 O1 56.60(16) . . . . ?
C18 N1 B1 O2 -63.09(15) . . . . ?
C18 N1 B1 N2 177.35(11) . . . . ?
B1 N1 C15 C10 5.41(18) . . . . ?
B1 N1 C15 C16 -175.21(11) . . . . ?
B1 N1 C18 C17 175.37(11) . . . . ?
B1 N2 C11 C10 -3.57(18) . . . . ?
B1 N2 C11 C12 177.27(11) . . . . ?
B1 N2 C14 C13 -177.74(11) . . . . ?
C20 O1 B1 O2 -179.84(11) . . . . ?
C20 O1 B1 N1 57.74(15) . . . . ?
C20 O1 B1 N2 -57.28(15) . . . . ?
C21 O2 B1 O1 176.74(11) . . . . ?
C21 O2 B1 N1 -60.18(15) . . . . ?
C21 O2 B1 N2 53.82(15) . . . . ?

_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 1.145
_oxdiff_exptl_absorpt_empirical_full_min 0.890
####################################################################### 
# 
# 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_meo_bodipy
_database_code_depnum_ccdc_archive 'CCDC 2040727'
loop_
_audit_author_name
_audit_author_address
'Tilo Soehnel'
;University of Auckland
New Zealand
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-12-13 downloaded from the CCDC.
;
_audit_creation_date             2020-10-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 B N2 O2'
_chemical_formula_sum            'C18 H19 B N2 O2'
_chemical_formula_weight         306.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H19BN2O2
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.6344(2)
_cell_length_b                   9.56650(10)
_cell_length_c                   23.8456(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.0920(10)
_cell_angle_gamma                90
_cell_volume                     3086.47(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14567
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.0840
_cell_measurement_theta_min      3.7820
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18118
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         5.664
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 -36.00   0.50    0.10    --  -47.48 -60.00  11.00   76
  2  ω   -111.00 -82.00   0.50    0.10    --  -47.48 -60.00  11.00   58
  3  ω    -29.00  22.00   0.50    0.10    --  -47.48  60.00 150.00  102
  4  ω   -145.00 -87.00   0.50    0.40    --  -90.25 -60.00  11.00  116
  5  ω   -100.00 -23.00   0.50    0.40    --  -90.25  60.00 150.00  154
  6  ω     29.00  67.00   0.50    0.40    --  101.53 -60.00  11.00   76
  7  ω     85.00 110.00   0.50    0.40    --  101.53 -60.00  11.00   50
  8  ω     81.00 171.00   0.50    0.40    --  101.53  60.00 150.00  180
  9  ω   -122.00 -27.00   0.50    0.10    --  -47.48 -57.00 -30.00  190
 10  ω   -119.00 -88.00   0.50    0.10    --  -47.48-125.00 -60.00   62
 11  ω   -118.00 -74.00   0.50    0.10    --  -47.48-125.00-120.00   88
 12  ω     19.00  68.00   0.50    0.10    --   47.48 -60.00  11.00   98
 13  ω     31.00  99.00   0.50    0.10    --   47.48-125.00-150.00  136
 14  ω     42.00  73.00   0.50    0.10    --   47.48  60.00 150.00   62
 15  ω     40.00  66.00   0.50    0.10    --   47.48  57.00 -90.00   52
 16  ω   -165.00-130.00   0.50    0.40    --  -90.25 -45.00-120.00   70
 17  ω   -147.00-116.00   0.50    0.40    --  -90.25 -94.00 120.00   62
 18  ω   -110.00 -71.00   0.50    0.40    --  -90.25 -45.00 -60.00   78
 19  ω   -162.00 -71.00   0.50    0.40    --  -90.25 -45.00 -90.00  182
 20  ω   -120.00 -73.00   0.50    0.40    --  -90.25 -45.00-120.00   94
 21  ω   -169.00-135.00   0.50    0.40    --  -90.25 -94.00-150.00   68
 22  ω   -129.00-103.00   0.50    0.40    --  -90.25 -94.00-150.00   52
 23  ω    -83.00 -33.00   0.50    0.40    --  -90.25 111.00-150.00  100
 24  ω    107.00 132.00   0.50    0.40    --  101.53 111.00 -90.00   50
 25  ω     83.00 109.00   0.50    0.40    --  101.53 -30.00   0.00   52
 26  ω     21.00  64.00   0.50    0.40    --  101.53 -30.00   0.00   86
 27  ω     25.00 110.00   0.50    0.40    --  101.53 -94.00  90.00  170
 28  ω     21.00 122.00   0.50    0.40    --  101.53 -30.00-150.00  202
 29  ω     77.00 111.00   0.50    0.40    --  101.53  77.00 -60.00   68
 30  ω     89.00 130.00   0.50    0.40    --  101.53  45.00-120.00   82
 31  ω     26.00 128.00   0.50    0.40    --  101.53 -77.00 -60.00  204
 32  ω     84.00 174.00   0.50    0.40    --  101.53  45.00  90.00  180
 33  ω    121.00 175.00   0.50    0.40    --  101.53  45.00 -90.00  108
 34  ω     81.00 109.00   0.50    0.40    --  101.53  45.00 -90.00   56
 35  ω     35.00  91.00   0.50    0.40    --  101.53-111.00   0.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0688166000
_diffrn_orient_matrix_UB_12      -0.0170934000
_diffrn_orient_matrix_UB_13      0.0461589000
_diffrn_orient_matrix_UB_21      0.0692026000
_diffrn_orient_matrix_UB_22      -0.1130643000
_diffrn_orient_matrix_UB_23      0.0288629000
_diffrn_orient_matrix_UB_31      0.0586723000
_diffrn_orient_matrix_UB_32      0.1133743000
_diffrn_orient_matrix_UB_33      0.0357007000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2674
_reflns_number_total             2826
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.00068(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.063
_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)+(0.0370P)²+2.5626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0824
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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 0.28119(5) 0.55933(9) 0.25462(3) 0.0190(2) Uani 1 1 d . . . . .
O2 O 0.18987(6) 0.60817(9) 0.33025(3) 0.0230(2) Uani 1 1 d . . . . .
N1 N 0.32246(7) 0.43161(10) 0.34523(4) 0.0167(2) Uani 1 1 d . . . . .
N2 N 0.36516(7) 0.68185(10) 0.33925(4) 0.0170(2) Uani 1 1 d . . . . .
C1 C 0.86701(9) 0.44469(14) 0.51895(5) 0.0256(3) Uani 1 1 d . . . . .
H1A H 0.899065 0.364054 0.505617 0.038 Uiso 1 1 calc R U . . .
H1B H 0.862141 0.434428 0.558563 0.038 Uiso 1 1 calc R U . . .
H1C H 0.904856 0.526799 0.512984 0.038 Uiso 1 1 calc R U . . .
C2 C 0.76515(8) 0.45848(12) 0.48716(5) 0.0187(2) Uani 1 1 d . . . . .
C3 C 0.73286(8) 0.37106(12) 0.44185(5) 0.0186(2) Uani 1 1 d . . . . .
H3 H 0.774296 0.300533 0.431821 0.022 Uiso 1 1 calc R U . . .
C4 C 0.63994(8) 0.38736(12) 0.41140(5) 0.0171(2) Uani 1 1 d . . . . .
H4 H 0.619797 0.327395 0.381489 0.020 Uiso 1 1 calc R U . . .
C5 C 0.57641(8) 0.49312(12) 0.42532(4) 0.0161(2) Uani 1 1 d . . . . .
C6 C 0.60796(8) 0.57884(12) 0.47175(5) 0.0183(2) Uani 1 1 d . . . . .
H6 H 0.566294 0.648474 0.482288 0.022 Uiso 1 1 calc R U . . .
C7 C 0.70036(8) 0.56104(12) 0.50208(5) 0.0195(3) Uani 1 1 d . . . . .
H7 H 0.719636 0.618434 0.532962 0.023 Uiso 1 1 calc R U . . .
C8 C 0.47976(8) 0.51765(12) 0.39100(4) 0.0156(2) Uani 1 1 d . . . . .
C9 C 0.41333(8) 0.40762(12) 0.37740(4) 0.0162(2) Uani 1 1 d . . . . .
C10 C 0.41605(8) 0.26525(12) 0.39413(5) 0.0185(2) Uani 1 1 d . . . . .
H10 H 0.467852 0.220447 0.416063 0.022 Uiso 1 1 calc R U . . .
C11 C 0.32770(9) 0.20552(12) 0.37185(5) 0.0210(3) Uani 1 1 d . . . . .
H11 H 0.308548 0.113113 0.375855 0.025 Uiso 1 1 calc R U . . .
C12 C 0.27235(8) 0.31121(12) 0.34200(5) 0.0197(3) Uani 1 1 d . . . . .
H12 H 0.209431 0.299191 0.322619 0.024 Uiso 1 1 calc R U . . .
C13 C 0.45509(8) 0.65352(12) 0.37183(4) 0.0163(2) Uani 1 1 d . . . . .
C14 C 0.51004(9) 0.77928(12) 0.37727(5) 0.0198(2) Uani 1 1 d . . . . .
H14 H 0.573069 0.790839 0.396576 0.024 Uiso 1 1 calc R U . . .
C15 C 0.45281(9) 0.88144(12) 0.34865(5) 0.0229(3) Uani 1 1 d . . . . .
H15 H 0.469626 0.975037 0.345345 0.027 Uiso 1 1 calc R U . . .
C16 C 0.36467(9) 0.81782(12) 0.32549(5) 0.0208(3) Uani 1 1 d . . . . .
H16 H 0.313063 0.863302 0.303663 0.025 Uiso 1 1 calc R U . . .
C17 C 0.37139(9) 0.54000(14) 0.23241(5) 0.0243(3) Uani 1 1 d . . . . .
H17A H 0.358436 0.520334 0.192704 0.036 Uiso 1 1 calc R U . . .
H17B H 0.406629 0.463108 0.251309 0.036 Uiso 1 1 calc R U . . .
H17C H 0.410518 0.623394 0.238086 0.036 Uiso 1 1 calc R U . . .
C18 C 0.11109(9) 0.63245(15) 0.28750(5) 0.0263(3) Uani 1 1 d . . . . .
H18A H 0.131639 0.697103 0.260452 0.040 Uiso 1 1 calc R U . . .
H18B H 0.056133 0.670927 0.303869 0.040 Uiso 1 1 calc R U . . .
H18C H 0.091703 0.545897 0.268981 0.040 Uiso 1 1 calc R U . . .
B1 B 0.28437(9) 0.57216(14) 0.31473(5) 0.0176(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
O1 C17 1.4100(14) . ?
O1 B1 1.4340(14) . ?
O2 C18 1.4058(14) . ?
O2 B1 1.4259(15) . ?
N1 C9 1.3934(14) . ?
N1 C12 1.3366(15) . ?
N1 B1 1.5853(15) . ?
N2 C13 1.3947(14) . ?
N2 C16 1.3413(15) . ?
N2 B1 1.5803(16) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.5037(15) . ?
C2 C3 1.3939(16) . ?
C2 C7 1.3954(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.3891(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.3982(16) . ?
C5 C6 1.4020(16) . ?
C5 C8 1.4817(15) . ?
C6 H6 0.9300 . ?
C6 C7 1.3836(16) . ?
C7 H7 0.9300 . ?
C8 C9 1.4003(16) . ?
C8 C13 1.4048(16) . ?
C9 C10 1.4184(16) . ?
C10 H10 0.9300 . ?
C10 C11 1.3790(16) . ?
C11 H11 0.9300 . ?
C11 C12 1.4021(17) . ?
C12 H12 0.9300 . ?
C13 C14 1.4148(16) . ?
C14 H14 0.9300 . ?
C14 C15 1.3779(17) . ?
C15 H15 0.9300 . ?
C15 C16 1.3985(17) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C17 O1 B1 117.81(9) . . ?
C18 O2 B1 119.06(9) . . ?
C9 N1 B1 127.66(9) . . ?
C12 N1 C9 107.65(9) . . ?
C12 N1 B1 124.63(9) . . ?
C13 N2 B1 127.00(9) . . ?
C16 N2 C13 107.59(10) . . ?
C16 N2 B1 124.83(10) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.46(11) . . ?
C3 C2 C7 118.05(10) . . ?
C7 C2 C1 120.49(11) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.21(10) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.59(10) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 118.17(10) . . ?
C4 C5 C8 121.22(10) . . ?
C6 C5 C8 120.59(10) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.77(11) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.4 . . ?
C6 C7 C2 121.16(11) . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C5 120.97(10) . . ?
C9 C8 C13 119.88(10) . . ?
C13 C8 C5 119.16(10) . . ?
N1 C9 C8 120.62(10) . . ?
N1 C9 C10 107.67(10) . . ?
C8 C9 C10 131.53(10) . . ?
C9 C10 H10 126.3 . . ?
C11 C10 C9 107.36(10) . . ?
C11 C10 H10 126.3 . . ?
C10 C11 H11 126.7 . . ?
C10 C11 C12 106.65(10) . . ?
C12 C11 H11 126.7 . . ?
N1 C12 C11 110.67(10) . . ?
N1 C12 H12 124.7 . . ?
C11 C12 H12 124.7 . . ?
N2 C13 C8 121.31(10) . . ?
N2 C13 C14 107.76(10) . . ?
C8 C13 C14 130.85(10) . . ?
C13 C14 H14 126.4 . . ?
C15 C14 C13 107.26(10) . . ?
C15 C14 H14 126.4 . . ?
C14 C15 H15 126.5 . . ?
C14 C15 C16 107.06(11) . . ?
C16 C15 H15 126.5 . . ?
N2 C16 C15 110.33(10) . . ?
N2 C16 H16 124.8 . . ?
C15 C16 H16 124.8 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 B1 N1 110.71(9) . . ?
O1 B1 N2 111.13(9) . . ?
O2 B1 O1 111.30(9) . . ?
O2 B1 N1 109.95(9) . . ?
O2 B1 N2 110.76(9) . . ?
N2 B1 N1 102.68(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C9 C10 C11 0.22(12) . . . . ?
N2 C13 C14 C15 0.56(13) . . . . ?
C1 C2 C3 C4 -177.77(10) . . . . ?
C1 C2 C7 C6 177.26(11) . . . . ?
C2 C3 C4 C5 0.43(17) . . . . ?
C3 C2 C7 C6 -2.11(17) . . . . ?
C3 C4 C5 C6 -1.95(16) . . . . ?
C3 C4 C5 C8 176.00(10) . . . . ?
C4 C5 C6 C7 1.44(16) . . . . ?
C4 C5 C8 C9 50.78(15) . . . . ?
C4 C5 C8 C13 -129.01(11) . . . . ?
C5 C6 C7 C2 0.60(17) . . . . ?
C5 C8 C9 N1 179.82(9) . . . . ?
C5 C8 C9 C10 5.30(18) . . . . ?
C5 C8 C13 N2 179.80(9) . . . . ?
C5 C8 C13 C14 3.25(18) . . . . ?
C6 C5 C8 C9 -131.32(11) . . . . ?
C6 C5 C8 C13 48.89(15) . . . . ?
C7 C2 C3 C4 1.60(16) . . . . ?
C8 C5 C6 C7 -176.52(10) . . . . ?
C8 C9 C10 C11 175.27(11) . . . . ?
C8 C13 C14 C15 177.47(11) . . . . ?
C9 N1 C12 C11 0.34(13) . . . . ?
C9 N1 B1 O1 108.53(12) . . . . ?
C9 N1 B1 O2 -128.08(11) . . . . ?
C9 N1 B1 N2 -10.16(14) . . . . ?
C9 C8 C13 N2 0.00(16) . . . . ?
C9 C8 C13 C14 -176.55(11) . . . . ?
C9 C10 C11 C12 -0.02(13) . . . . ?
C10 C11 C12 N1 -0.20(13) . . . . ?
C12 N1 C9 C8 -176.04(10) . . . . ?
C12 N1 C9 C10 -0.34(12) . . . . ?
C12 N1 B1 O1 -68.31(14) . . . . ?
C12 N1 B1 O2 55.09(14) . . . . ?
C12 N1 B1 N2 173.01(10) . . . . ?
C13 N2 C16 C15 -0.34(13) . . . . ?
C13 N2 B1 O1 -108.73(12) . . . . ?
C13 N2 B1 O2 127.01(11) . . . . ?
C13 N2 B1 N1 9.67(14) . . . . ?
C13 C8 C9 N1 -0.38(16) . . . . ?
C13 C8 C9 C10 -174.91(11) . . . . ?
C13 C14 C15 C16 -0.75(13) . . . . ?
C14 C15 C16 N2 0.69(14) . . . . ?
C16 N2 C13 C8 -177.40(10) . . . . ?
C16 N2 C13 C14 -0.14(12) . . . . ?
C16 N2 B1 O1 61.44(14) . . . . ?
C16 N2 B1 O2 -62.82(14) . . . . ?
C16 N2 B1 N1 179.84(10) . . . . ?
C17 O1 B1 O2 172.84(10) . . . . ?
C17 O1 B1 N1 -64.55(13) . . . . ?
C17 O1 B1 N2 48.88(13) . . . . ?
C18 O2 B1 O1 -3.10(15) . . . . ?
C18 O2 B1 N1 -126.15(11) . . . . ?
C18 O2 B1 N2 121.06(11) . . . . ?
B1 N1 C9 C8 6.69(16) . . . . ?
B1 N1 C9 C10 -177.60(10) . . . . ?
B1 N1 C12 C11 177.71(10) . . . . ?
B1 N2 C13 C8 -5.85(16) . . . . ?
B1 N2 C13 C14 171.41(10) . . . . ?
B1 N2 C16 C15 -172.12(10) . . . . ?

_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 1.089
_oxdiff_exptl_absorpt_empirical_full_min 0.931
####################################################################### 
# 
# 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_dk44_2
_database_code_depnum_ccdc_archive 'CCDC 2040728'
loop_
_audit_author_name
_audit_author_address
'Tilo Soehnel'
;University of Auckland
New Zealand
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-12-13 downloaded from the CCDC.
;
_audit_creation_date             2020-10-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C37 H32 B2 N4 O5, 0.669(C2 H3 N), 0.205(C H2 Cl2)'
_chemical_formula_sum            'C38.55 H34.42 B2 Cl0.41 N4.67 O5'
_chemical_formula_weight         679.20
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H32B2N5O5
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'
Cl Cl 0.3639 0.7018 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   11.0231(2)
_cell_length_b                   11.6298(2)
_cell_length_c                   26.1050(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3346.58(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18049
_cell_measurement_temperature    110.0(9)
_cell_measurement_theta_max      78.6390
_cell_measurement_theta_min      3.4220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.011
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
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            ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1421
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -7 -6 0.0310
-4 1 -13 0.0276
1 5 3 0.0454
2 0 5 0.0360
0 0 -1 0.0202
-2 -1 5 0.0284
-5 2 -2 0.0269
1 0 -5 0.0199
5 -4 5 0.0360
-2 -1 16 0.0161
-6 3 7 0.0276
3 6 -7 0.0431
-5 -5 -4 0.0378

_exptl_crystal_size_max          0.083
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.041
loop_
_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
-1.0096 -6.9901 -5.9754 -0.7311 0.6584 0.1874
-4.0019 1.0067 -12.9606 -0.2999 0.2604 -0.8712
1.0064 4.9933 2.9806 0.4511 -0.5090 -0.1620
2.0011 -0.0032 4.9801 0.1206 -0.1819 0.3425
-0.0003 0.0004 -0.9995 -0.0442 -0.0064 -0.0386
-1.9991 -1.0001 5.0170 0.2473 0.3299 0.1137
-4.9971 2.0016 -1.9590 0.3098 0.3532 -0.5922
0.9982 0.0016 -5.0064 -0.2709 -0.1387 -0.1180
4.9958 -4.0009 4.9612 -0.3248 -0.1655 0.8490
-1.9957 -1.0048 16.0117 0.7331 0.4000 0.5380
-5.9930 2.9973 7.0436 0.8311 0.4332 -0.3904
3.0040 5.9955 -7.0340 -0.0170 -0.8707 -0.4686
-5.0057 -4.9907 -3.9451 -0.2948 0.9301 -0.1758

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            27509
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.236
_diffrn_reflns_theta_min         5.784
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.0(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  25.00   0.50    0.91    --  -47.48  57.00 120.00  186
  2  ω   -117.00 -70.00   0.50    0.91    --  -47.48-125.00 -60.00   94
  3  ω   -124.00 -20.00   0.50    0.91    --  -47.48 -78.00   2.00  208
  4  ω     46.00 133.00   0.50    3.63    --  111.75 -66.00 121.00  174
  5  ω    135.00 161.00   0.50    3.63    --  111.75  25.00   0.00   52
  6  ω    107.00 132.00   0.50    3.63    --  111.75  25.00   0.00   50
  7  ω     93.00 154.00   0.50    3.63    --  111.75  64.00 -60.00  122
  8  ω    100.00 178.00   0.50    3.63    --  111.75  64.00 -30.00  156
  9  ω    152.00 178.00   0.50    3.63    --  111.75  38.00  90.00   52
 10  ω    125.00 150.00   0.50    3.63    --  111.75  78.00 127.00   50
 11  ω     86.00 163.00   0.50    3.63    --  111.75  78.00  13.00  154
 12  ω     95.00 178.00   0.50    3.63    --  111.75  64.00 -90.00  166
 13  ω    124.00 177.00   0.50    3.63    --  111.75 111.00-150.00  106
 14  ω     91.00 156.00   0.50    3.63    --  111.75  25.00-180.00  130
 15  ω     85.00 171.00   0.50    3.63    --  111.75  77.00   0.00  172
 16  ω     92.00 120.00   0.50    3.63    --  111.75  38.00  90.00   56
 17  ω     46.00  93.00   0.50    3.63    --  111.75 -92.00-120.00   94
 18  ω    112.00 146.00   0.50    3.63    --  111.75 -92.00-120.00   68
 19  ω   -123.00 -71.00   0.50    0.91    --  -47.48-125.00  90.00  104
 20  ω   -166.00 -63.00   0.50    3.63    --  -90.25 -78.00   2.00  206
 21  ω   -124.00 -99.00   0.50    0.91    --  -47.48-125.00-150.00   50
 22  ω   -163.00 -67.00   0.50    3.63    --  -90.25 -78.00-111.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0497081000
_diffrn_orient_matrix_UB_12      0.0739615000
_diffrn_orient_matrix_UB_13      0.0442321000
_diffrn_orient_matrix_UB_21      -0.1068933000
_diffrn_orient_matrix_UB_22      -0.0841934000
_diffrn_orient_matrix_UB_23      0.0063733000
_diffrn_orient_matrix_UB_31      0.0751321000
_diffrn_orient_matrix_UB_32      -0.0705957000
_diffrn_orient_matrix_UB_33      0.0385332000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5784
_reflns_number_total             6115
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 2389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       0.00074(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         6115
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.075
_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)+(0.0562P)²+0.7978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0995
_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. Uiso/Uaniso restraints and constraints
Uanis(C40) = Uanis(C39)
3. Same fragment restrains
{Cl1, C40, Cl2} sigma for 1-2: 0.01, 1-3: 0.02
as in
{O1, O3, N1}
4. Others
 Sof(Cl1)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(Cl2)=FVAR(1)
 Sof(N5)=Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C39)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C40(H40A,H40B)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C28(H28), C29(H29), C30(H30),
  C32(H32), C33(H33), C35(H35), C36(H36)
5.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C)
;
_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
O1 O -0.16080(17) -0.06931(15) -0.08397(7) 0.0241(4) Uani 1 1 d D . . . .
O3 O 0.00841(18) -0.42019(16) -0.10388(7) 0.0254(4) Uani 1 1 d . . . . .
N1 N -0.0361(2) 0.10366(18) -0.07589(8) 0.0212(5) Uani 1 1 d D . . . .
O2 O -0.1198(2) -0.32211(16) -0.15896(7) 0.0285(4) Uani 1 1 d . . . . .
O4 O -0.14402(19) -0.24787(16) -0.04178(7) 0.0271(4) Uani 1 1 d . . . . .
O5 O 0.03988(17) -0.07306(16) -0.04336(7) 0.0244(4) Uani 1 1 d . . . . .
N2 N -0.1368(2) 0.02213(19) 0.00116(9) 0.0231(5) Uani 1 1 d . . . . .
N3 N -0.0410(2) -0.51002(19) -0.18846(8) 0.0242(5) Uani 1 1 d . . . . .
N4 N -0.1936(2) -0.5083(2) -0.11991(8) 0.0239(5) Uani 1 1 d . . . . .
C1 C -0.1631(3) -0.1889(2) -0.08906(10) 0.0235(6) Uani 1 1 d . . . . .
H1 H -0.243484 -0.210596 -0.101849 0.028 Uiso 1 1 calc R U . . .
C2 C -0.0683(3) -0.2377(2) -0.12633(10) 0.0262(6) Uani 1 1 d . . . . .
H2 H -0.029111 -0.176422 -0.146070 0.031 Uiso 1 1 calc R U . . .
C3 C 0.0241(3) -0.3017(2) -0.09219(10) 0.0248(6) Uani 1 1 d . . . . .
H3 H 0.107367 -0.276162 -0.098733 0.030 Uiso 1 1 calc R U . . .
C4 C -0.0162(3) -0.2742(2) -0.03748(10) 0.0258(6) Uani 1 1 d . . . . .
H4 H -0.005730 -0.342569 -0.015996 0.031 Uiso 1 1 calc R U . . .
C5 C 0.0500(3) -0.1740(2) -0.01334(10) 0.0267(6) Uani 1 1 d . . . . .
H5A H 0.016658 -0.159560 0.020443 0.032 Uiso 1 1 calc R U . . .
H5B H 0.134971 -0.193560 -0.009332 0.032 Uiso 1 1 calc R U . . .
C6 C 0.0133(3) 0.1167(2) -0.12229(10) 0.0238(5) Uani 1 1 d . . . . .
H6 H 0.021833 0.058363 -0.146386 0.029 Uiso 1 1 calc R U . . .
C7 C 0.0505(3) 0.2308(2) -0.12944(10) 0.0259(6) Uani 1 1 d . . . . .
H7 H 0.087907 0.260843 -0.158427 0.031 Uiso 1 1 calc R U . . .
C8 C 0.0210(2) 0.2903(2) -0.08532(10) 0.0240(5) Uani 1 1 d . . . . .
H8 H 0.033635 0.368201 -0.079186 0.029 Uiso 1 1 calc R U . . .
C9 C -0.0319(2) 0.2102(2) -0.05132(10) 0.0204(5) Uani 1 1 d . . . . .
C10 C -0.0787(2) 0.2238(2) -0.00196(10) 0.0218(5) Uani 1 1 d . . . . .
C11 C -0.1305(2) 0.1303(2) 0.02382(10) 0.0218(5) Uani 1 1 d . . . . .
C12 C -0.1829(3) 0.1236(2) 0.07310(11) 0.0267(6) Uani 1 1 d . . . . .
H12 H -0.189311 0.183218 0.096692 0.032 Uiso 1 1 calc R U . . .
C13 C -0.2230(3) 0.0120(3) 0.07970(11) 0.0311(6) Uani 1 1 d . . . . .
H13 H -0.261832 -0.017662 0.108439 0.037 Uiso 1 1 calc R U . . .
C14 C -0.1939(3) -0.0478(2) 0.03494(11) 0.0291(6) Uani 1 1 d . . . . .
H14 H -0.211331 -0.124940 0.029135 0.035 Uiso 1 1 calc R U . . .
C15 C -0.0720(3) 0.3368(2) 0.02423(10) 0.0225(5) Uani 1 1 d . . . . .
C16 C 0.0397(3) 0.3900(2) 0.03274(10) 0.0236(5) Uani 1 1 d . . . . .
H16 H 0.110366 0.356827 0.020114 0.028 Uiso 1 1 calc R U . . .
C17 C 0.0454(3) 0.4923(2) 0.06003(10) 0.0255(6) Uani 1 1 d . . . . .
H17 H 0.120333 0.526030 0.066461 0.031 Uiso 1 1 calc R U . . .
C18 C -0.0602(3) 0.5453(2) 0.07793(10) 0.0255(6) Uani 1 1 d . . . . .
C19 C -0.1715(3) 0.4934(2) 0.06769(10) 0.0263(6) Uani 1 1 d . . . . .
H19 H -0.242707 0.529060 0.078332 0.032 Uiso 1 1 calc R U . . .
C20 C -0.1775(3) 0.3899(2) 0.04194(11) 0.0257(6) Uani 1 1 d . . . . .
H20 H -0.252366 0.355219 0.036360 0.031 Uiso 1 1 calc R U . . .
C21 C -0.0549(3) 0.6556(3) 0.10810(12) 0.0337(7) Uani 1 1 d . . . . .
H21A H 0.023610 0.690186 0.103989 0.051 Uiso 1 1 calc R U . . .
H21B H -0.068724 0.639488 0.143688 0.051 Uiso 1 1 calc R U . . .
H21C H -0.116110 0.707453 0.095843 0.051 Uiso 1 1 calc R U . . .
C22 C 0.0605(3) -0.4908(2) -0.21574(11) 0.0293(6) Uani 1 1 d . . . . .
H22 H 0.114867 -0.431075 -0.209766 0.035 Uiso 1 1 calc R U . . .
C23 C 0.0727(3) -0.5730(3) -0.25420(11) 0.0297(6) Uani 1 1 d . . . . .
H23 H 0.135267 -0.577942 -0.278021 0.036 Uiso 1 1 calc R U . . .
C24 C -0.0261(3) -0.6459(2) -0.25017(10) 0.0258(6) Uani 1 1 d . . . . .
H24 H -0.042137 -0.709367 -0.270765 0.031 Uiso 1 1 calc R U . . .
C25 C -0.0976(2) -0.6065(2) -0.20929(10) 0.0219(5) Uani 1 1 d . . . . .
C26 C -0.2029(3) -0.6524(2) -0.18702(10) 0.0223(5) Uani 1 1 d . . . . .
C27 C -0.2499(3) -0.6037(2) -0.14249(10) 0.0229(5) Uani 1 1 d . . . . .
C28 C -0.3504(3) -0.6339(3) -0.11175(11) 0.0282(6) Uani 1 1 d . . . . .
H28 H -0.404909 -0.693378 -0.117947 0.034 Uiso 1 1 calc R U . . .
C29 C -0.3528(3) -0.5593(3) -0.07105(11) 0.0328(7) Uani 1 1 d . . . . .
H29 H -0.408742 -0.558937 -0.044398 0.039 Uiso 1 1 calc R U . . .
C30 C -0.2549(3) -0.4837(3) -0.07724(11) 0.0295(6) Uani 1 1 d . . . . .
H30 H -0.235441 -0.424562 -0.054727 0.035 Uiso 1 1 calc R U . . .
C31 C -0.2634(2) -0.7537(2) -0.21038(10) 0.0235(5) Uani 1 1 d . . . . .
C32 C -0.2924(3) -0.8503(3) -0.18158(11) 0.0292(6) Uani 1 1 d . . . . .
H32 H -0.270726 -0.853634 -0.147185 0.035 Uiso 1 1 calc R U . . .
C33 C -0.3538(3) -0.9422(3) -0.20386(13) 0.0373(7) Uani 1 1 d . . . . .
H33 H -0.372146 -1.006369 -0.184089 0.045 Uiso 1 1 calc R U . . .
C34 C -0.3884(3) -0.9398(3) -0.25523(13) 0.0388(7) Uani 1 1 d . . . . .
C35 C -0.3563(3) -0.8440(3) -0.28419(12) 0.0332(7) Uani 1 1 d . . . . .
H35 H -0.376211 -0.841664 -0.318792 0.040 Uiso 1 1 calc R U . . .
C36 C -0.2950(3) -0.7519(2) -0.26235(10) 0.0269(6) Uani 1 1 d . . . . .
H36 H -0.274760 -0.688532 -0.282355 0.032 Uiso 1 1 calc R U . . .
C37 C -0.4581(5) -1.0367(3) -0.27986(17) 0.0623(12) Uani 1 1 d . . . . .
H37A H -0.407055 -1.075307 -0.304188 0.093 Uiso 1 1 calc R U . . .
H37B H -0.527984 -1.006181 -0.297084 0.093 Uiso 1 1 calc R U . . .
H37C H -0.483584 -1.090138 -0.254005 0.093 Uiso 1 1 calc R U . . .
B1 B -0.0733(3) -0.0134(2) -0.05107(11) 0.0214(6) Uani 1 1 d . . . . .
B2 B -0.0845(3) -0.4358(3) -0.14206(11) 0.0240(6) Uani 1 1 d . . . . .
N5 N -0.2550(6) -1.4868(5) -0.31027(18) 0.0542(17) Uani 0.669(10) 1 d . . P A 1
C38 C -0.3025(7) -1.3058(6) -0.2575(3) 0.0585(19) Uani 0.669(10) 1 d . . P A 1
H38A H -0.262171 -1.309236 -0.224933 0.088 Uiso 0.669(10) 1 calc R U P A 1
H38B H -0.388424 -1.299825 -0.252257 0.088 Uiso 0.669(10) 1 calc R U P A 1
H38C H -0.274321 -1.239892 -0.276174 0.088 Uiso 0.669(10) 1 calc R U P A 1
C39 C -0.2763(6) -1.4081(5) -0.2861(3) 0.0471(16) Uani 0.669(10) 1 d . . P A 1
Cl1 Cl -0.3205(6) -1.3936(6) -0.3086(2) 0.061(2) Uani 0.205(4) 1 d D . P B 2
C40 C -0.263(2) -1.359(2) -0.2506(8) 0.0471(16) Uani 0.205(4) 1 d . . P B 2
H40A H -0.191952 -1.310985 -0.255531 0.057 Uiso 0.205(4) 1 calc R U P B 2
H40B H -0.236289 -1.429144 -0.233743 0.057 Uiso 0.205(4) 1 calc R U P B 2
Cl2 Cl -0.3634(5) -1.2880(8) -0.2105(3) 0.094(3) Uani 0.205(4) 1 d D . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.398(3) . ?
O1 B1 1.446(3) . ?
O3 C3 1.421(3) . ?
O3 B2 1.441(4) . ?
N1 C6 1.337(4) . ?
N1 C9 1.396(3) . ?
N1 B1 1.562(3) . ?
O2 C2 1.418(3) . ?
O2 B2 1.448(4) . ?
O4 C1 1.427(3) . ?
O4 C4 1.447(4) . ?
O5 C5 1.416(3) . ?
O5 B1 1.442(4) . ?
N2 C11 1.391(3) . ?
N2 C14 1.355(4) . ?
N2 B1 1.587(4) . ?
N3 C22 1.345(4) . ?
N3 C25 1.394(3) . ?
N3 B2 1.562(4) . ?
N4 C27 1.401(4) . ?
N4 C30 1.334(4) . ?
N4 B2 1.578(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.537(4) . ?
C2 H2 0.9800 . ?
C2 C3 1.544(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.530(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.512(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C7 1.401(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.413(4) . ?
C9 C10 1.397(4) . ?
C10 C11 1.401(4) . ?
C10 C15 1.483(4) . ?
C11 C12 1.413(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.397(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.395(4) . ?
C15 C20 1.395(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.397(4) . ?
C18 C19 1.393(4) . ?
C18 C21 1.507(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.381(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 0.9300 . ?
C22 C23 1.393(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.385(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.404(4) . ?
C25 C26 1.403(4) . ?
C26 C27 1.393(4) . ?
C26 C31 1.485(4) . ?
C27 C28 1.412(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.372(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.400(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.389(4) . ?
C31 C36 1.401(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.392(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.394(5) . ?
C34 C35 1.392(5) . ?
C34 C37 1.507(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.389(4) . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
N5 C39 1.137(9) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C38 C39 1.433(10) . ?
Cl1 C40 1.69(2) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 Cl2 1.73(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
C1 O1 B1 121.1(2) . . ?
C3 O3 B2 110.9(2) . . ?
C6 N1 C9 107.6(2) . . ?
C6 N1 B1 125.6(2) . . ?
C9 N1 B1 126.3(2) . . ?
C2 O2 B2 110.0(2) . . ?
C1 O4 C4 108.19(19) . . ?
C5 O5 B1 123.0(2) . . ?
C11 N2 B1 125.3(2) . . ?
C14 N2 C11 106.8(2) . . ?
C14 N2 B1 127.4(2) . . ?
C22 N3 C25 107.5(2) . . ?
C22 N3 B2 125.0(2) . . ?
C25 N3 B2 127.5(2) . . ?
C27 N4 B2 127.3(2) . . ?
C30 N4 C27 107.3(2) . . ?
C30 N4 B2 125.3(2) . . ?
O1 C1 O4 113.2(2) . . ?
O1 C1 H1 107.7 . . ?
O1 C1 C2 114.5(2) . . ?
O4 C1 H1 107.7 . . ?
O4 C1 C2 105.7(2) . . ?
C2 C1 H1 107.7 . . ?
O2 C2 C1 111.3(2) . . ?
O2 C2 H2 111.3 . . ?
O2 C2 C3 106.1(2) . . ?
C1 C2 H2 111.3 . . ?
C1 C2 C3 105.1(2) . . ?
C3 C2 H2 111.3 . . ?
O3 C3 C2 105.3(2) . . ?
O3 C3 H3 111.8 . . ?
O3 C3 C4 111.6(2) . . ?
C2 C3 H3 111.8 . . ?
C4 C3 C2 104.3(2) . . ?
C4 C3 H3 111.8 . . ?
O4 C4 C3 104.7(2) . . ?
O4 C4 H4 109.3 . . ?
O4 C4 C5 109.8(2) . . ?
C3 C4 H4 109.3 . . ?
C5 C4 C3 114.3(2) . . ?
C5 C4 H4 109.3 . . ?
O5 C5 C4 111.7(2) . . ?
O5 C5 H5A 109.3 . . ?
O5 C5 H5B 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
N1 C6 H6 124.8 . . ?
N1 C6 C7 110.3(2) . . ?
C7 C6 H6 124.8 . . ?
C6 C7 H7 126.4 . . ?
C8 C7 C6 107.1(2) . . ?
C8 C7 H7 126.4 . . ?
C7 C8 H8 126.6 . . ?
C7 C8 C9 106.9(2) . . ?
C9 C8 H8 126.6 . . ?
N1 C9 C8 108.1(2) . . ?
N1 C9 C10 120.8(2) . . ?
C10 C9 C8 131.1(2) . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 C15 120.5(2) . . ?
C11 C10 C15 119.2(2) . . ?
N2 C11 C10 121.2(2) . . ?
N2 C11 C12 108.5(2) . . ?
C10 C11 C12 130.3(3) . . ?
C11 C12 H12 126.4 . . ?
C13 C12 C11 107.2(3) . . ?
C13 C12 H12 126.4 . . ?
C12 C13 H13 126.6 . . ?
C12 C13 C14 106.8(3) . . ?
C14 C13 H13 126.6 . . ?
N2 C14 C13 110.6(2) . . ?
N2 C14 H14 124.7 . . ?
C13 C14 H14 124.7 . . ?
C16 C15 C10 120.7(2) . . ?
C20 C15 C10 120.2(2) . . ?
C20 C15 C16 119.1(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C21 121.2(3) . . ?
C19 C18 C17 118.6(2) . . ?
C19 C18 C21 120.2(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.5(3) . . ?
C19 C20 H20 119.8 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 H22 124.8 . . ?
N3 C22 C23 110.3(3) . . ?
C23 C22 H22 124.8 . . ?
C22 C23 H23 126.6 . . ?
C24 C23 C22 106.8(3) . . ?
C24 C23 H23 126.6 . . ?
C23 C24 H24 126.3 . . ?
C23 C24 C25 107.4(2) . . ?
C25 C24 H24 126.3 . . ?
N3 C25 C24 107.9(2) . . ?
N3 C25 C26 121.0(2) . . ?
C26 C25 C24 130.9(3) . . ?
C25 C26 C31 120.2(2) . . ?
C27 C26 C25 119.9(2) . . ?
C27 C26 C31 119.9(2) . . ?
N4 C27 C28 107.8(2) . . ?
C26 C27 N4 120.5(2) . . ?
C26 C27 C28 131.7(3) . . ?
C27 C28 H28 126.3 . . ?
C29 C28 C27 107.3(3) . . ?
C29 C28 H28 126.3 . . ?
C28 C29 H29 126.5 . . ?
C28 C29 C30 107.0(3) . . ?
C30 C29 H29 126.5 . . ?
N4 C30 C29 110.6(3) . . ?
N4 C30 H30 124.7 . . ?
C29 C30 H30 124.7 . . ?
C32 C31 C26 121.5(2) . . ?
C32 C31 C36 118.7(3) . . ?
C36 C31 C26 119.8(2) . . ?
C31 C32 H32 119.8 . . ?
C31 C32 C33 120.4(3) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 119.3 . . ?
C32 C33 C34 121.3(3) . . ?
C34 C33 H33 119.3 . . ?
C33 C34 C37 122.4(3) . . ?
C35 C34 C33 117.9(3) . . ?
C35 C34 C37 119.7(3) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 C34 121.2(3) . . ?
C36 C35 H35 119.4 . . ?
C31 C36 H36 119.8 . . ?
C35 C36 C31 120.4(3) . . ?
C35 C36 H36 119.8 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O1 B1 N1 108.7(2) . . ?
O1 B1 N2 109.5(2) . . ?
N1 B1 N2 104.2(2) . . ?
O5 B1 O1 116.3(2) . . ?
O5 B1 N1 104.5(2) . . ?
O5 B1 N2 112.8(2) . . ?
O3 B2 O2 106.7(2) . . ?
O3 B2 N3 112.8(2) . . ?
O3 B2 N4 110.8(2) . . ?
O2 B2 N3 110.5(2) . . ?
O2 B2 N4 113.3(2) . . ?
N3 B2 N4 102.9(2) . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C39 C38 H38A 109.5 . . ?
C39 C38 H38B 109.5 . . ?
C39 C38 H38C 109.5 . . ?
N5 C39 C38 177.5(8) . . ?
Cl1 C40 H40A 108.7 . . ?
Cl1 C40 H40B 108.7 . . ?
Cl1 C40 Cl2 114.4(13) . . ?
H40A C40 H40B 107.6 . . ?
Cl2 C40 H40A 108.7 . . ?
Cl2 C40 H40B 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 -135.3(2) . . . . ?
O1 C1 C2 C3 110.3(2) . . . . ?
O3 C3 C4 O4 -88.5(3) . . . . ?
O3 C3 C4 C5 151.3(2) . . . . ?
N1 C6 C7 C8 -0.6(3) . . . . ?
N1 C9 C10 C11 0.2(4) . . . . ?
N1 C9 C10 C15 178.9(2) . . . . ?
O2 C2 C3 O3 -6.5(3) . . . . ?
O2 C2 C3 C4 -124.1(2) . . . . ?
O4 C1 C2 O2 99.5(2) . . . . ?
O4 C1 C2 C3 -14.9(3) . . . . ?
O4 C4 C5 O5 -61.2(3) . . . . ?
N2 C11 C12 C13 -1.2(3) . . . . ?
N3 C22 C23 C24 0.0(3) . . . . ?
N3 C25 C26 C27 -2.1(4) . . . . ?
N3 C25 C26 C31 178.7(2) . . . . ?
N4 C27 C28 C29 -1.1(3) . . . . ?
C1 O1 B1 N1 145.3(2) . . . . ?
C1 O1 B1 O5 27.8(3) . . . . ?
C1 O1 B1 N2 -101.5(3) . . . . ?
C1 O4 C4 C3 -36.0(3) . . . . ?
C1 O4 C4 C5 87.1(2) . . . . ?
C1 C2 C3 O3 111.6(2) . . . . ?
C1 C2 C3 C4 -6.0(3) . . . . ?
C2 O2 B2 O3 -10.4(3) . . . . ?
C2 O2 B2 N3 -133.4(2) . . . . ?
C2 O2 B2 N4 111.7(3) . . . . ?
C2 C3 C4 O4 24.7(3) . . . . ?
C2 C3 C4 C5 -95.6(3) . . . . ?
C3 O3 B2 O2 6.1(3) . . . . ?
C3 O3 B2 N3 127.6(2) . . . . ?
C3 O3 B2 N4 -117.6(2) . . . . ?
C3 C4 C5 O5 56.1(3) . . . . ?
C4 O4 C1 O1 -94.1(3) . . . . ?
C4 O4 C1 C2 32.0(3) . . . . ?
C5 O5 B1 O1 -71.9(3) . . . . ?
C5 O5 B1 N1 168.2(2) . . . . ?
C5 O5 B1 N2 55.7(3) . . . . ?
C6 N1 C9 C8 0.9(3) . . . . ?
C6 N1 C9 C10 179.3(2) . . . . ?
C6 N1 B1 O1 -58.6(3) . . . . ?
C6 N1 B1 O5 66.3(3) . . . . ?
C6 N1 B1 N2 -175.2(2) . . . . ?
C6 C7 C8 C9 1.1(3) . . . . ?
C7 C8 C9 N1 -1.3(3) . . . . ?
C7 C8 C9 C10 -179.4(3) . . . . ?
C8 C9 C10 C11 178.1(3) . . . . ?
C8 C9 C10 C15 -3.1(4) . . . . ?
C9 N1 C6 C7 -0.2(3) . . . . ?
C9 N1 B1 O1 131.3(3) . . . . ?
C9 N1 B1 O5 -103.8(3) . . . . ?
C9 N1 B1 N2 14.7(3) . . . . ?
C9 C10 C11 N2 -0.1(4) . . . . ?
C9 C10 C11 C12 -179.9(3) . . . . ?
C9 C10 C15 C16 -58.5(3) . . . . ?
C9 C10 C15 C20 123.2(3) . . . . ?
C10 C11 C12 C13 178.7(3) . . . . ?
C10 C15 C16 C17 -176.1(2) . . . . ?
C10 C15 C20 C19 178.1(2) . . . . ?
C11 N2 C14 C13 -1.2(3) . . . . ?
C11 N2 B1 O1 -130.5(3) . . . . ?
C11 N2 B1 N1 -14.4(3) . . . . ?
C11 N2 B1 O5 98.3(3) . . . . ?
C11 C10 C15 C16 120.3(3) . . . . ?
C11 C10 C15 C20 -58.0(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 N2 0.4(3) . . . . ?
C14 N2 C11 C10 -178.4(2) . . . . ?
C14 N2 C11 C12 1.4(3) . . . . ?
C14 N2 B1 O1 58.1(3) . . . . ?
C14 N2 B1 N1 174.2(2) . . . . ?
C14 N2 B1 O5 -73.1(3) . . . . ?
C15 C10 C11 N2 -178.8(2) . . . . ?
C15 C10 C11 C12 1.3(4) . . . . ?
C15 C16 C17 C18 -2.0(4) . . . . ?
C16 C15 C20 C19 -0.2(4) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C16 C17 C18 C21 179.3(2) . . . . ?
C17 C18 C19 C20 2.2(4) . . . . ?
C18 C19 C20 C15 -2.0(4) . . . . ?
C20 C15 C16 C17 2.2(4) . . . . ?
C21 C18 C19 C20 -177.3(3) . . . . ?
C22 N3 C25 C24 0.4(3) . . . . ?
C22 N3 C25 C26 176.2(2) . . . . ?
C22 N3 B2 O3 -51.6(4) . . . . ?
C22 N3 B2 O2 67.7(3) . . . . ?
C22 N3 B2 N4 -171.1(2) . . . . ?
C22 C23 C24 C25 0.3(3) . . . . ?
C23 C24 C25 N3 -0.5(3) . . . . ?
C23 C24 C25 C26 -175.6(3) . . . . ?
C24 C25 C26 C27 172.5(3) . . . . ?
C24 C25 C26 C31 -6.6(4) . . . . ?
C25 N3 C22 C23 -0.3(3) . . . . ?
C25 N3 B2 O3 128.4(3) . . . . ?
C25 N3 B2 O2 -112.3(3) . . . . ?
C25 N3 B2 N4 8.9(3) . . . . ?
C25 C26 C27 N4 0.6(4) . . . . ?
C25 C26 C27 C28 -177.9(3) . . . . ?
C25 C26 C31 C32 128.6(3) . . . . ?
C25 C26 C31 C36 -52.9(4) . . . . ?
C26 C27 C28 C29 177.6(3) . . . . ?
C26 C31 C32 C33 177.2(3) . . . . ?
C26 C31 C36 C35 -177.2(3) . . . . ?
C27 N4 C30 C29 -1.0(3) . . . . ?
C27 N4 B2 O3 -131.3(3) . . . . ?
C27 N4 B2 O2 108.9(3) . . . . ?
C27 N4 B2 N3 -10.5(3) . . . . ?
C27 C26 C31 C32 -50.6(4) . . . . ?
C27 C26 C31 C36 127.9(3) . . . . ?
C27 C28 C29 C30 0.5(3) . . . . ?
C28 C29 C30 N4 0.4(4) . . . . ?
C30 N4 C27 C26 -177.6(3) . . . . ?
C30 N4 C27 C28 1.3(3) . . . . ?
C30 N4 B2 O3 53.9(4) . . . . ?
C30 N4 B2 O2 -65.9(3) . . . . ?
C30 N4 B2 N3 174.7(3) . . . . ?
C31 C26 C27 N4 179.8(2) . . . . ?
C31 C26 C27 C28 1.2(4) . . . . ?
C31 C32 C33 C34 -0.4(5) . . . . ?
C32 C31 C36 C35 1.3(4) . . . . ?
C32 C33 C34 C35 2.0(5) . . . . ?
C32 C33 C34 C37 -178.2(4) . . . . ?
C33 C34 C35 C36 -1.9(5) . . . . ?
C34 C35 C36 C31 0.3(5) . . . . ?
C36 C31 C32 C33 -1.3(4) . . . . ?
C37 C34 C35 C36 178.2(4) . . . . ?
B1 O1 C1 O4 40.5(3) . . . . ?
B1 O1 C1 C2 -80.7(3) . . . . ?
B1 N1 C6 C7 -171.8(2) . . . . ?
B1 N1 C9 C8 172.5(2) . . . . ?
B1 N1 C9 C10 -9.2(4) . . . . ?
B1 O5 C5 C4 66.9(3) . . . . ?
B1 N2 C11 C10 8.7(4) . . . . ?
B1 N2 C11 C12 -171.5(2) . . . . ?
B1 N2 C14 C13 171.5(3) . . . . ?
B2 O3 C3 C2 0.2(3) . . . . ?
B2 O3 C3 C4 112.7(3) . . . . ?
B2 O2 C2 C1 -103.4(3) . . . . ?
B2 O2 C2 C3 10.4(3) . . . . ?
B2 N3 C22 C23 179.7(2) . . . . ?
B2 N3 C25 C24 -179.5(2) . . . . ?
B2 N3 C25 C26 -3.8(4) . . . . ?
B2 N4 C27 C26 6.9(4) . . . . ?
B2 N4 C27 C28 -174.3(2) . . . . ?
B2 N4 C30 C29 174.6(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 1.169
_oxdiff_exptl_absorpt_empirical_full_min 0.895
