# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_dht-100k_auto
_database_code_depnum_ccdc_archive 'CCDC 2235711'
loop_
_audit_author_name
_audit_author_address
'Huangting Ding'
;YunNan University
China
;
_audit_update_record             
;
2023-01-12 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_audit_creation_date             2022-06-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H31 B N2'
_chemical_formula_sum            'C27 H31 B N2'
_chemical_formula_weight         394.35
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.4528(3)
_cell_length_b                   9.0066(3)
_cell_length_c                   20.1003(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.462(2)
_cell_angle_gamma                90
_cell_volume                     2254.32(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9467
_cell_measurement_temperature    90.0(3)
_cell_measurement_theta_max      29.2480
_cell_measurement_theta_min      1.9070
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.809
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15775
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.809
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.347
_diffrn_reflns_theta_min         1.917
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      90.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.809
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  56.00   0.50    0.49    --   10.52 -99.00   0.00  132
  2  ω      8.00  34.00   0.50    0.49    --  -11.30 -99.00 -60.00   52
  3  ω    -15.00  30.00   0.50    0.49    --  -11.30 -94.00 141.00   90
  4  ω    -19.00  17.00   0.50    0.49    --   10.52 -19.00 -60.00   72
  5  ω      8.00  33.00   0.50    0.49    --   10.52 -99.00-150.00   50
  6  ω    -39.00  25.00   0.50    0.49    --  -11.30  94.00-108.00  128
  7  ω    -17.00  20.00   0.50    0.49    --   10.52 -19.00-180.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0506734000
_diffrn_orient_matrix_UB_12      -0.0135019000
_diffrn_orient_matrix_UB_13      -0.0146454000
_diffrn_orient_matrix_UB_21      0.0151273000
_diffrn_orient_matrix_UB_22      0.0747052000
_diffrn_orient_matrix_UB_23      0.0062468000
_diffrn_orient_matrix_UB_31      0.0210964000
_diffrn_orient_matrix_UB_32      -0.0210855000
_diffrn_orient_matrix_UB_33      0.0314927000
_diffrn_oxdiff_digest_frames     
;
012f8e0550348e6b445befa84ed0b17b9200038f3d5
;
_diffrn_oxdiff_digest_hkl        
;
012c9af43e78883a704260a3936bd959519a1c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4060
_reflns_number_total             5018
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         5018
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.097
_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)+(0.0549P)²+0.5472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1194
_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:
 C4(H4), C8(H8), C9(H9), C16(H16), C13(H13), C25(H25), C22(H22)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C18(H18A,H18B,H18C), C15(H15A,H15B,H15C),
 C12(H12A,H12B,H12C), C27(H27A,H27B,H27C), C24(H24A,H24B,H24C), 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
B1 B 0.70661(11) 0.32650(17) 0.43552(7) 0.0175(3) Uani 1 1 d . . . . .
C1 C 0.86100(12) -0.10457(16) 0.68665(7) 0.0275(3) Uani 1 1 d . . . . .
H1A H 0.802762 -0.160535 0.665233 0.041 Uiso 1 1 calc GR . . . .
H1B H 0.869286 -0.137397 0.732892 0.041 Uiso 1 1 calc GR . . . .
H1C H 0.928111 -0.121957 0.662738 0.041 Uiso 1 1 calc GR . . . .
C2 C 0.87096(11) 0.14127(17) 0.74167(7) 0.0261(3) Uani 1 1 d . . . . .
H2A H 0.935667 0.196738 0.729652 0.039 Uiso 1 1 calc GR . . . .
H2B H 0.887010 0.076203 0.779541 0.039 Uiso 1 1 calc GR . . . .
H2C H 0.813964 0.210994 0.753812 0.039 Uiso 1 1 calc GR . . . .
C3 C 0.80542(9) 0.11879(15) 0.62680(6) 0.0181(3) Uani 1 1 d . . . . .
C4 C 0.79203(9) 0.27342(15) 0.62251(6) 0.0179(3) Uani 1 1 d . . . . .
H4 H 0.804987 0.333123 0.660704 0.022 Uiso 1 1 calc R . . . .
C5 C 0.76011(9) 0.34047(14) 0.56321(6) 0.0166(3) Uani 1 1 d . . . . .
C7 C 0.73635(10) 0.25901(14) 0.50472(6) 0.0171(3) Uani 1 1 d . . . . .
C8 C 0.74795(10) 0.10468(14) 0.51161(6) 0.0186(3) Uani 1 1 d . . . . .
H8 H 0.730107 0.044115 0.474439 0.022 Uiso 1 1 calc R . . . .
C9 C 0.78355(10) 0.03537(15) 0.56883(6) 0.0188(3) Uani 1 1 d . . . . .
H9 H 0.793429 -0.069216 0.569234 0.023 Uiso 1 1 calc R . . . .
C6 C 0.75037(10) 0.50065(15) 0.56662(6) 0.0196(3) Uani 1 1 d . . . . .
C10 C 0.63663(10) 0.22959(14) 0.38634(6) 0.0172(3) Uani 1 1 d . . . . .
C17 C 0.67075(10) 0.20070(14) 0.32072(6) 0.0174(3) Uani 1 1 d . . . . .
C18 C 0.77262(11) 0.26559(16) 0.29262(6) 0.0237(3) Uani 1 1 d . . . . .
H18A H 0.759987 0.369116 0.279744 0.036 Uiso 1 1 calc GR . . . .
H18B H 0.794232 0.208331 0.253488 0.036 Uiso 1 1 calc GR . . . .
H18C H 0.829744 0.261437 0.326389 0.036 Uiso 1 1 calc GR . . . .
C16 C 0.61063(10) 0.10792(14) 0.27935(6) 0.0187(3) Uani 1 1 d . . . . .
H16 H 0.635373 0.088077 0.235655 0.022 Uiso 1 1 calc R . . . .
C14 C 0.51552(10) 0.04382(15) 0.30039(6) 0.0198(3) Uani 1 1 d . . . . .
C15 C 0.45345(11) -0.05937(17) 0.25519(7) 0.0287(3) Uani 1 1 d . . . . .
H15A H 0.378440 -0.063689 0.269446 0.043 Uiso 1 1 calc GR . . . .
H15B H 0.485007 -0.158940 0.257381 0.043 Uiso 1 1 calc GR . . . .
H15C H 0.456566 -0.022506 0.209373 0.043 Uiso 1 1 calc GR . . . .
C13 C 0.48016(10) 0.07563(15) 0.36390(6) 0.0204(3) Uani 1 1 d . . . . .
H13 H 0.414173 0.034418 0.378449 0.024 Uiso 1 1 calc R . . . .
C11 C 0.53852(10) 0.16629(15) 0.40708(6) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.49093(10) 0.19905(17) 0.47438(7) 0.0239(3) Uani 1 1 d . . . . .
H12A H 0.524079 0.134254 0.507901 0.036 Uiso 1 1 calc GR . . . .
H12B H 0.413332 0.181118 0.472840 0.036 Uiso 1 1 calc GR . . . .
H12C H 0.504514 0.303041 0.486077 0.036 Uiso 1 1 calc GR . . . .
C19 C 0.75185(10) 0.48331(14) 0.41619(6) 0.0167(3) Uani 1 1 d . . . . .
C26 C 0.86384(10) 0.51156(15) 0.41941(6) 0.0172(3) Uani 1 1 d . . . . .
C27 C 0.94388(10) 0.39069(15) 0.43583(7) 0.0212(3) Uani 1 1 d . . . . .
H27A H 0.947999 0.377480 0.484180 0.032 Uiso 1 1 calc GR . . . .
H27B H 1.014697 0.418666 0.419008 0.032 Uiso 1 1 calc GR . . . .
H27C H 0.920861 0.297519 0.414961 0.032 Uiso 1 1 calc GR . . . .
C25 C 0.90240(10) 0.65209(15) 0.40437(6) 0.0190(3) Uani 1 1 d . . . . .
H25 H 0.977741 0.668639 0.405262 0.023 Uiso 1 1 calc R . . . .
C23 C 0.83465(11) 0.76948(15) 0.38805(6) 0.0201(3) Uani 1 1 d . . . . .
C24 C 0.87999(12) 0.91930(16) 0.37077(8) 0.0285(3) Uani 1 1 d . . . . .
H24A H 0.936449 0.945620 0.402904 0.043 Uiso 1 1 calc GR . . . .
H24B H 0.822736 0.993850 0.372184 0.043 Uiso 1 1 calc GR . . . .
H24C H 0.910328 0.916009 0.325955 0.043 Uiso 1 1 calc GR . . . .
C22 C 0.72498(10) 0.74126(15) 0.38471(6) 0.0197(3) Uani 1 1 d . . . . .
H22 H 0.677208 0.820259 0.374245 0.024 Uiso 1 1 calc R . . . .
C20 C 0.68334(10) 0.60028(14) 0.39631(6) 0.0180(3) Uani 1 1 d . . . . .
C21 C 0.56452(10) 0.57543(16) 0.38563(7) 0.0239(3) Uani 1 1 d . . . . .
H21A H 0.553167 0.515606 0.345462 0.036 Uiso 1 1 calc GR . . . .
H21B H 0.528364 0.671407 0.380396 0.036 Uiso 1 1 calc GR . . . .
H21C H 0.534933 0.523131 0.424110 0.036 Uiso 1 1 calc GR . . . .
N1 N 0.83570(9) 0.05209(13) 0.68531(5) 0.0224(3) Uani 1 1 d . . . . .
N2 N 0.74495(10) 0.62650(14) 0.57535(6) 0.0272(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C7 1.5599(19) . ?
B1 C10 1.5763(18) . ?
B1 C19 1.5705(19) . ?
C1 N1 1.4460(18) . ?
C2 N1 1.4537(18) . ?
C3 C4 1.4052(18) . ?
C3 C9 1.4111(18) . ?
C3 N1 1.3709(16) . ?
C4 C5 1.3914(17) . ?
C5 C7 1.4150(17) . ?
C5 C6 1.4495(18) . ?
C7 C8 1.4041(18) . ?
C8 C9 1.3787(18) . ?
C6 N2 1.1490(18) . ?
C10 C17 1.4132(17) . ?
C10 C11 1.4141(17) . ?
C17 C18 1.5105(17) . ?
C17 C16 1.3929(18) . ?
C16 C14 1.3867(18) . ?
C14 C15 1.5085(18) . ?
C14 C13 1.3836(18) . ?
C13 C11 1.3921(18) . ?
C11 C12 1.5105(18) . ?
C19 C26 1.4185(17) . ?
C19 C20 1.4114(17) . ?
C26 C27 1.5107(18) . ?
C26 C25 1.3879(18) . ?
C25 C23 1.3903(19) . ?
C23 C24 1.5044(19) . ?
C23 C22 1.3903(18) . ?
C22 C20 1.3918(18) . ?
C20 C21 1.5101(18) . ?

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
C7 B1 C10 118.01(11) . . ?
C7 B1 C19 119.21(11) . . ?
C19 B1 C10 122.71(11) . . ?
C4 C3 C9 117.07(11) . . ?
N1 C3 C4 121.24(12) . . ?
N1 C3 C9 121.67(12) . . ?
C5 C4 C3 121.04(12) . . ?
C4 C5 C7 122.89(12) . . ?
C4 C5 C6 114.51(11) . . ?
C7 C5 C6 122.58(11) . . ?
C5 C7 B1 125.82(12) . . ?
C8 C7 B1 119.81(11) . . ?
C8 C7 C5 114.25(11) . . ?
C9 C8 C7 124.23(12) . . ?
C8 C9 C3 120.42(12) . . ?
N2 C6 C5 173.79(13) . . ?
C17 C10 B1 121.24(11) . . ?
C17 C10 C11 117.89(11) . . ?
C11 C10 B1 120.86(11) . . ?
C10 C17 C18 122.51(11) . . ?
C16 C17 C10 120.23(11) . . ?
C16 C17 C18 117.25(11) . . ?
C14 C16 C17 121.59(12) . . ?
C16 C14 C15 120.50(12) . . ?
C13 C14 C16 118.31(12) . . ?
C13 C14 C15 121.19(12) . . ?
C14 C13 C11 121.89(12) . . ?
C10 C11 C12 122.10(11) . . ?
C13 C11 C10 120.04(12) . . ?
C13 C11 C12 117.80(11) . . ?
C26 C19 B1 120.30(11) . . ?
C20 C19 B1 121.61(11) . . ?
C20 C19 C26 118.08(12) . . ?
C19 C26 C27 121.83(12) . . ?
C25 C26 C19 119.70(12) . . ?
C25 C26 C27 118.42(11) . . ?
C26 C25 C23 122.31(12) . . ?
C25 C23 C24 120.56(12) . . ?
C22 C23 C25 117.79(12) . . ?
C22 C23 C24 121.55(12) . . ?
C23 C22 C20 121.73(12) . . ?
C19 C20 C21 121.26(12) . . ?
C22 C20 C19 120.22(11) . . ?
C22 C20 C21 118.51(11) . . ?
C1 N1 C2 117.40(11) . . ?
C3 N1 C1 120.13(11) . . ?
C3 N1 C2 120.38(12) . . ?

_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 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.839
####################################################################### 
# 
# 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_9010-bno-jian-100k_autored
_database_code_depnum_ccdc_archive 'CCDC 2235712'
loop_
_audit_author_name
_audit_author_address
'Huangting Ding'
;YunNan University
China
;
_audit_update_record             
;
2023-01-12 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_audit_creation_date             2022-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H34 B N O'
_chemical_formula_sum            'C27 H34 B N O'
_chemical_formula_weight         399.36
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1599(3)
_cell_length_b                   8.1094(3)
_cell_length_c                   23.5966(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.497(3)
_cell_angle_gamma                90
_cell_volume                     2280.16(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10835
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.3090
_cell_measurement_theta_min      1.7160
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17896
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.147
_diffrn_reflns_theta_min         1.709
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00  -4.00   0.50    1.08    --   10.52 -19.00-120.00  138
  2  ω     19.00  54.00   0.50    1.08    --   10.52 -99.00-180.00   70
  3  ω     11.00  36.00   0.50    1.08    --   10.52-114.00 -54.00   50
  4  ω     -9.00  54.00   0.50    1.08    --   10.52 -99.00 150.00  126
  5  ω    -17.00  33.00   0.50    1.08    --   10.52  57.00 -30.00  100
  6  ω     58.00  85.00   0.50    1.08    --   10.52  57.00 -30.00   54
  7  ω    -18.00  29.00   0.50    1.08    --   10.52  77.00  90.00   94
  8  ω    -62.00 -37.00   0.50    1.08    --  -11.30 114.00  36.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0135201000
_diffrn_orient_matrix_UB_12      0.0851438000
_diffrn_orient_matrix_UB_13      -0.0004419000
_diffrn_orient_matrix_UB_21      -0.0426585000
_diffrn_orient_matrix_UB_22      -0.0127754000
_diffrn_orient_matrix_UB_23      -0.0248771000
_diffrn_orient_matrix_UB_31      -0.0392249000
_diffrn_orient_matrix_UB_32      -0.0154995000
_diffrn_orient_matrix_UB_33      0.0179450000
_diffrn_oxdiff_digest_frames     
;
0139cd0ca4d8f27d6be81f8d786415823e00682711d
;
_diffrn_oxdiff_digest_hkl        
;
01aa1ade3ad1adeb9918a221dc130d9ec35975
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4138
_reflns_number_total             5154
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.072
_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)+(0.0594P)²+0.8841P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1274
_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:
 C4(H4), C5(H5), C7(H7), C13(H13), C16(H16), C22(H22), C25(H25)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C9(H9A,H9B,H9C), C12(H12A,H12B,H12C),
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C24(H24A,H24B,
 H24C), C27(H27A,H27B,H27C)
;
_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 0.04933(8) -0.11507(13) 0.25772(4) 0.0206(2) Uani 1 1 d . . . . .
N1 N 0.17164(9) -0.13998(15) 0.17310(5) 0.0197(3) Uani 1 1 d . . . . .
C1 C 0.25415(13) -0.1770(2) 0.13786(7) 0.0270(3) Uani 1 1 d . . . . .
H1A H 0.230291 -0.274721 0.114156 0.040 Uiso 1 1 calc GR . . . .
H1B H 0.327122 -0.198244 0.163061 0.040 Uiso 1 1 calc GR . . . .
H1C H 0.260550 -0.082922 0.112648 0.040 Uiso 1 1 calc GR . . . .
C2 C 0.05916(12) -0.1278(2) 0.13796(6) 0.0251(3) Uani 1 1 d . . . . .
H2A H 0.055747 -0.034412 0.111292 0.038 Uiso 1 1 calc GR . . . .
H2B H 0.005000 -0.110887 0.163107 0.038 Uiso 1 1 calc GR . . . .
H2C H 0.040960 -0.229769 0.115804 0.038 Uiso 1 1 calc GR . . . .
C3 C 0.20351(11) -0.02643(17) 0.21816(6) 0.0171(3) Uani 1 1 d . . . . .
C4 C 0.30070(11) 0.06905(18) 0.22383(6) 0.0185(3) Uani 1 1 d . . . . .
H4 H 0.344245 0.063213 0.194633 0.022 Uiso 1 1 calc R . . . .
C5 C 0.33545(11) 0.17231(18) 0.27097(6) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.401504 0.236357 0.272883 0.022 Uiso 1 1 calc R . . . .
C6 C 0.27579(11) 0.18442(17) 0.31564(6) 0.0164(3) Uani 1 1 d . . . . .
C7 C 0.17784(11) 0.08717(17) 0.31014(6) 0.0171(3) Uani 1 1 d . . . . .
H7 H 0.135268 0.092036 0.339771 0.020 Uiso 1 1 calc R . . . .
C8 C 0.14176(11) -0.01479(17) 0.26319(6) 0.0165(3) Uani 1 1 d . . . . .
C9 C -0.00581(12) -0.1224(2) 0.30555(6) 0.0243(3) Uani 1 1 d . . . . .
H9A H -0.068268 -0.200756 0.297074 0.036 Uiso 1 1 calc GR . . . .
H9B H -0.034637 -0.012848 0.312397 0.036 Uiso 1 1 calc GR . . . .
H9C H 0.047545 -0.158528 0.340093 0.036 Uiso 1 1 calc GR . . . .
C10 C 0.39076(11) 0.45319(17) 0.36414(6) 0.0164(3) Uani 1 1 d . . . . .
C11 C 0.49142(11) 0.48170(17) 0.40480(6) 0.0167(3) Uani 1 1 d . . . . .
C12 C 0.53633(11) 0.35526(18) 0.45044(6) 0.0203(3) Uani 1 1 d . . . . .
H12A H 0.478999 0.330411 0.473080 0.030 Uiso 1 1 calc GR . . . .
H12B H 0.603441 0.398937 0.476067 0.030 Uiso 1 1 calc GR . . . .
H12C H 0.555725 0.254269 0.431832 0.030 Uiso 1 1 calc GR . . . .
C13 C 0.55265(11) 0.62589(18) 0.40221(6) 0.0181(3) Uani 1 1 d . . . . .
H13 H 0.619567 0.643586 0.430106 0.022 Uiso 1 1 calc R . . . .
C14 C 0.51824(11) 0.74440(17) 0.35983(6) 0.0184(3) Uani 1 1 d . . . . .
C15 C 0.58563(12) 0.89935(19) 0.35723(7) 0.0238(3) Uani 1 1 d . . . . .
H15A H 0.609435 0.944403 0.396291 0.036 Uiso 1 1 calc GR . . . .
H15B H 0.539350 0.980821 0.332609 0.036 Uiso 1 1 calc GR . . . .
H15C H 0.651903 0.873526 0.341102 0.036 Uiso 1 1 calc GR . . . .
C16 C 0.42028(11) 0.71550(18) 0.31959(6) 0.0187(3) Uani 1 1 d . . . . .
H16 H 0.395906 0.795123 0.290244 0.022 Uiso 1 1 calc R . . . .
C17 C 0.35659(11) 0.57338(17) 0.32090(6) 0.0175(3) Uani 1 1 d . . . . .
C18 C 0.24842(12) 0.55791(19) 0.27655(6) 0.0232(3) Uani 1 1 d . . . . .
H18A H 0.263663 0.504333 0.241691 0.035 Uiso 1 1 calc GR . . . .
H18B H 0.216972 0.667869 0.266644 0.035 Uiso 1 1 calc GR . . . .
H18C H 0.194610 0.491500 0.292600 0.035 Uiso 1 1 calc GR . . . .
C19 C 0.26498(10) 0.26415(17) 0.42529(6) 0.0164(3) Uani 1 1 d . . . . .
C20 C 0.20326(11) 0.38496(18) 0.44890(6) 0.0177(3) Uani 1 1 d . . . . .
C21 C 0.19278(12) 0.56026(18) 0.42664(6) 0.0225(3) Uani 1 1 d . . . . .
H21A H 0.267699 0.608800 0.430446 0.034 Uiso 1 1 calc GR . . . .
H21B H 0.148728 0.625119 0.449190 0.034 Uiso 1 1 calc GR . . . .
H21C H 0.155111 0.560466 0.385849 0.034 Uiso 1 1 calc GR . . . .
C22 C 0.14918(11) 0.34353(19) 0.49382(6) 0.0211(3) Uani 1 1 d . . . . .
H22 H 0.106948 0.425574 0.508749 0.025 Uiso 1 1 calc R . . . .
C23 C 0.15515(11) 0.1864(2) 0.51733(6) 0.0228(3) Uani 1 1 d . . . . .
C24 C 0.09468(14) 0.1435(2) 0.56541(7) 0.0335(4) Uani 1 1 d . . . . .
H24A H 0.082460 0.244035 0.586380 0.050 Uiso 1 1 calc GR . . . .
H24B H 0.140185 0.065852 0.592080 0.050 Uiso 1 1 calc GR . . . .
H24C H 0.022162 0.092917 0.548957 0.050 Uiso 1 1 calc GR . . . .
C25 C 0.22065(11) 0.07036(19) 0.49620(6) 0.0214(3) Uani 1 1 d . . . . .
H25 H 0.228348 -0.036629 0.512918 0.026 Uiso 1 1 calc R . . . .
C26 C 0.27541(11) 0.10643(18) 0.45115(6) 0.0184(3) Uani 1 1 d . . . . .
C27 C 0.34875(13) -0.02524(19) 0.43285(7) 0.0240(3) Uani 1 1 d . . . . .
H27A H 0.304101 -0.092381 0.402108 0.036 Uiso 1 1 calc GR . . . .
H27B H 0.379128 -0.095582 0.466054 0.036 Uiso 1 1 calc GR . . . .
H27C H 0.410651 0.026702 0.418498 0.036 Uiso 1 1 calc GR . . . .
B1 B 0.31331(12) 0.2996(2) 0.36874(7) 0.0165(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 C8 1.3724(16) . ?
O1 C9 1.4242(16) . ?
N1 C1 1.4563(18) . ?
N1 C2 1.4546(18) . ?
N1 C3 1.4015(18) . ?
C3 C4 1.3968(19) . ?
C3 C8 1.4213(18) . ?
C4 C5 1.389(2) . ?
C5 C6 1.3972(18) . ?
C6 C7 1.4127(19) . ?
C6 B1 1.556(2) . ?
C7 C8 1.3820(19) . ?
C10 C11 1.4156(18) . ?
C10 C17 1.4124(19) . ?
C10 B1 1.578(2) . ?
C11 C12 1.5084(19) . ?
C11 C13 1.394(2) . ?
C13 C14 1.390(2) . ?
C14 C15 1.508(2) . ?
C14 C16 1.3873(19) . ?
C16 C17 1.392(2) . ?
C17 C18 1.5141(19) . ?
C19 C20 1.4142(19) . ?
C19 C26 1.412(2) . ?
C19 B1 1.5878(19) . ?
C20 C21 1.512(2) . ?
C20 C22 1.3953(19) . ?
C22 C23 1.386(2) . ?
C23 C24 1.5104(19) . ?
C23 C25 1.388(2) . ?
C25 C26 1.3932(19) . ?
C26 C27 1.508(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C9 117.14(11) . . ?
C2 N1 C1 111.41(11) . . ?
C3 N1 C1 116.79(11) . . ?
C3 N1 C2 118.30(11) . . ?
N1 C3 C8 120.22(12) . . ?
C4 C3 N1 122.52(12) . . ?
C4 C3 C8 117.04(12) . . ?
C5 C4 C3 121.82(12) . . ?
C4 C5 C6 121.72(12) . . ?
C5 C6 C7 116.52(12) . . ?
C5 C6 B1 122.45(12) . . ?
C7 C6 B1 121.03(12) . . ?
C8 C7 C6 122.33(12) . . ?
O1 C8 C3 115.80(12) . . ?
O1 C8 C7 123.58(12) . . ?
C7 C8 C3 120.57(12) . . ?
C11 C10 B1 121.97(12) . . ?
C17 C10 C11 117.84(12) . . ?
C17 C10 B1 120.04(12) . . ?
C10 C11 C12 120.93(12) . . ?
C13 C11 C10 120.30(13) . . ?
C13 C11 C12 118.75(12) . . ?
C14 C13 C11 121.64(12) . . ?
C13 C14 C15 121.15(12) . . ?
C16 C14 C13 118.03(13) . . ?
C16 C14 C15 120.82(13) . . ?
C14 C16 C17 122.02(13) . . ?
C10 C17 C18 122.15(12) . . ?
C16 C17 C10 120.16(12) . . ?
C16 C17 C18 117.63(12) . . ?
C20 C19 B1 121.34(12) . . ?
C26 C19 C20 117.80(12) . . ?
C26 C19 B1 120.71(12) . . ?
C19 C20 C21 121.94(12) . . ?
C22 C20 C19 120.00(13) . . ?
C22 C20 C21 118.06(12) . . ?
C23 C22 C20 122.04(13) . . ?
C22 C23 C24 121.19(14) . . ?
C22 C23 C25 117.88(13) . . ?
C25 C23 C24 120.91(14) . . ?
C23 C25 C26 121.83(14) . . ?
C19 C26 C27 121.66(12) . . ?
C25 C26 C19 120.30(13) . . ?
C25 C26 C27 118.00(13) . . ?
C6 B1 C10 120.10(12) . . ?
C6 B1 C19 118.02(12) . . ?
C10 B1 C19 121.76(12) . . ?

_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 1.293
_oxdiff_exptl_absorpt_empirical_full_min 0.699
####################################################################### 
# 
# 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_8293-100k_autored
_database_code_depnum_ccdc_archive 'CCDC 2235714'
loop_
_audit_author_name
_audit_author_address
'Huangting Ding'
;YunNan University
China
;
_audit_update_record             
;
2023-01-12 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_audit_creation_date             2022-09-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H34 B N O'
_chemical_formula_sum            'C27 H34 B N O'
_chemical_formula_weight         399.36
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1627(2)
_cell_length_b                   22.1971(6)
_cell_length_c                   12.6370(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.613(2)
_cell_angle_gamma                90
_cell_volume                     2289.55(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12655
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.3670
_cell_measurement_theta_min      1.8250
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21238
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.295
_diffrn_reflns_theta_min         1.835
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  14.00   0.50    0.62    --   10.52 -19.00-180.00   56
  2  ω    -61.00 -23.00   0.50    0.62    --   10.52 -19.00-180.00   76
  3  ω    -12.00  84.00   0.50    0.62    --   10.52  28.00-171.00  192
  4  ω     -8.00  32.00   0.50    0.62    --  -11.30 -99.00-180.00   80
  5  ω      0.00  25.00   0.50    0.62    --  -11.30 -99.00   0.00   50
  6  ω     -9.00  17.00   0.50    0.62    --  -11.30 -99.00  30.00   52
  7  ω     16.00  60.00   0.50    0.62    --   10.60-108.00 -67.00   88
  8  ω    -11.00  14.00   0.50    0.62    --   10.60 -99.00  90.00   50
  9  ω     16.00  43.00   0.50    0.62    --   10.60 -99.00 120.00   54
 10  ω     -6.00  32.00   0.50    0.62    --  -11.46 -99.00  90.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0100089000
_diffrn_orient_matrix_UB_12      0.0117780000
_diffrn_orient_matrix_UB_13      0.0517077000
_diffrn_orient_matrix_UB_21      0.0307353000
_diffrn_orient_matrix_UB_22      0.0282267000
_diffrn_orient_matrix_UB_23      -0.0171380000
_diffrn_orient_matrix_UB_31      -0.0806219000
_diffrn_orient_matrix_UB_32      0.0092908000
_diffrn_orient_matrix_UB_33      -0.0135705000
_diffrn_oxdiff_digest_frames     
;
01f25bab7369e0f7e216b2787d685cb99d007744bfa
;
_diffrn_oxdiff_digest_hkl        
;
012eaa21b6cb6fc87ac01b2245ad5b82dc6487
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4230
_reflns_number_total             5233
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.066
_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)+(0.0595P)²+0.6422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1213
_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:
 C4(H4), C5(H5), C8(H8), C13(H13), C16(H16), C22(H22), C25(H25)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C9(H9A,H9B,H9C), C12(H12A,H12B,H12C),
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C24(H24A,H24B,
 H24C), C27(H27A,H27B,H27C)
;
_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
B1 B 0.30940(16) 0.36327(6) 0.63388(11) 0.0160(3) Uani 1 1 d . . . . .
C1 C -0.18827(16) 0.12823(6) 0.70744(10) 0.0232(3) Uani 1 1 d . . . . .
H1A H -0.285685 0.153062 0.719092 0.035 Uiso 1 1 calc GR . . . .
H1B H -0.116986 0.129842 0.770267 0.035 Uiso 1 1 calc GR . . . .
H1C H -0.221622 0.086455 0.694300 0.035 Uiso 1 1 calc GR . . . .
C2 C -0.12345(17) 0.12009(6) 0.51695(11) 0.0255(3) Uani 1 1 d . . . . .
H2A H -0.020203 0.101157 0.496192 0.038 Uiso 1 1 calc GR . . . .
H2B H -0.157373 0.149235 0.462744 0.038 Uiso 1 1 calc GR . . . .
H2C H -0.208151 0.089105 0.524089 0.038 Uiso 1 1 calc GR . . . .
C3 C 0.00019(14) 0.20003(5) 0.62408(10) 0.0178(3) Uani 1 1 d . . . . .
C4 C 0.09479(15) 0.21826(5) 0.53723(10) 0.0186(3) Uani 1 1 d . . . . .
H4 H 0.090946 0.195983 0.473065 0.022 Uiso 1 1 calc R . . . .
C5 C 0.19327(14) 0.26872(5) 0.54575(10) 0.0171(3) Uani 1 1 d . . . . .
H5 H 0.259205 0.279062 0.486979 0.021 Uiso 1 1 calc R . . . .
C6 C 0.20196(14) 0.30567(5) 0.63587(10) 0.0162(2) Uani 1 1 d . . . . .
C7 C 0.10600(14) 0.28613(5) 0.72145(9) 0.0163(2) Uani 1 1 d . . . . .
C8 C 0.01093(14) 0.23444(5) 0.71733(10) 0.0171(3) Uani 1 1 d . . . . .
H8 H -0.047640 0.222114 0.778177 0.020 Uiso 1 1 calc R . . . .
C9 C -0.00525(17) 0.31314(6) 0.88930(11) 0.0253(3) Uani 1 1 d . . . . .
H9A H -0.114186 0.314761 0.856055 0.038 Uiso 1 1 calc GR . . . .
H9B H 0.004855 0.345412 0.941888 0.038 Uiso 1 1 calc GR . . . .
H9C H 0.009739 0.274054 0.924126 0.038 Uiso 1 1 calc GR . . . .
C10 C 0.27176(14) 0.42032(5) 0.70435(9) 0.0161(2) Uani 1 1 d . . . . .
C11 C 0.11329(14) 0.44591(5) 0.70506(10) 0.0183(3) Uani 1 1 d . . . . .
C12 C -0.02110(15) 0.42390(6) 0.63154(11) 0.0250(3) Uani 1 1 d . . . . .
H12A H 0.026166 0.412495 0.563450 0.038 Uiso 1 1 calc GR . . . .
H12B H -0.101651 0.456094 0.620503 0.038 Uiso 1 1 calc GR . . . .
H12C H -0.074964 0.388849 0.662978 0.038 Uiso 1 1 calc GR . . . .
C13 C 0.07735(15) 0.49304(6) 0.77338(10) 0.0213(3) Uani 1 1 d . . . . .
H13 H -0.030072 0.509515 0.772489 0.026 Uiso 1 1 calc R . . . .
C14 C 0.19325(16) 0.51685(6) 0.84291(10) 0.0222(3) Uani 1 1 d . . . . .
C15 C 0.15000(19) 0.56664(7) 0.91859(12) 0.0324(3) Uani 1 1 d . . . . .
H15A H 0.039664 0.581548 0.902027 0.049 Uiso 1 1 calc GR . . . .
H15B H 0.229024 0.599615 0.911767 0.049 Uiso 1 1 calc GR . . . .
H15C H 0.153173 0.551165 0.991208 0.049 Uiso 1 1 calc GR . . . .
C16 C 0.35061(15) 0.49327(6) 0.83924(10) 0.0206(3) Uani 1 1 d . . . . .
H16 H 0.432883 0.509754 0.884406 0.025 Uiso 1 1 calc R . . . .
C17 C 0.39189(14) 0.44635(5) 0.77171(10) 0.0172(3) Uani 1 1 d . . . . .
C18 C 0.56615(15) 0.42338(6) 0.77501(10) 0.0226(3) Uani 1 1 d . . . . .
H18A H 0.567371 0.381785 0.800994 0.034 Uiso 1 1 calc GR . . . .
H18B H 0.632064 0.448780 0.822490 0.034 Uiso 1 1 calc GR . . . .
H18C H 0.612009 0.424689 0.703697 0.034 Uiso 1 1 calc GR . . . .
C19 C 0.46120(14) 0.36176(5) 0.55708(9) 0.0157(2) Uani 1 1 d . . . . .
C20 C 0.48091(14) 0.40324(5) 0.47405(10) 0.0161(2) Uani 1 1 d . . . . .
C21 C 0.35128(15) 0.45043(6) 0.45178(10) 0.0205(3) Uani 1 1 d . . . . .
H21A H 0.250472 0.430724 0.427088 0.031 Uiso 1 1 calc GR . . . .
H21B H 0.390268 0.478109 0.397125 0.031 Uiso 1 1 calc GR . . . .
H21C H 0.329159 0.473026 0.516702 0.031 Uiso 1 1 calc GR . . . .
C22 C 0.61663(14) 0.40005(6) 0.40864(10) 0.0181(3) Uani 1 1 d . . . . .
H22 H 0.627653 0.428517 0.353030 0.022 Uiso 1 1 calc R . . . .
C23 C 0.73666(15) 0.35617(6) 0.42272(10) 0.0196(3) Uani 1 1 d . . . . .
C24 C 0.88067(16) 0.35192(7) 0.34982(12) 0.0277(3) Uani 1 1 d . . . . .
H24A H 0.847448 0.331128 0.284631 0.042 Uiso 1 1 calc GR . . . .
H24B H 0.969127 0.329329 0.384722 0.042 Uiso 1 1 calc GR . . . .
H24C H 0.919265 0.392523 0.332623 0.042 Uiso 1 1 calc GR . . . .
C25 C 0.71798(15) 0.31558(6) 0.50506(10) 0.0196(3) Uani 1 1 d . . . . .
H25 H 0.799558 0.285679 0.516372 0.023 Uiso 1 1 calc R . . . .
C26 C 0.58346(14) 0.31729(5) 0.57164(10) 0.0176(3) Uani 1 1 d . . . . .
C27 C 0.57573(15) 0.27119(6) 0.65939(11) 0.0231(3) Uani 1 1 d . . . . .
H27A H 0.511327 0.287341 0.717930 0.035 Uiso 1 1 calc GR . . . .
H27B H 0.686929 0.262019 0.684579 0.035 Uiso 1 1 calc GR . . . .
H27C H 0.523933 0.234315 0.632602 0.035 Uiso 1 1 calc GR . . . .
N1 N -0.10075(14) 0.15077(5) 0.61716(9) 0.0259(3) Uani 1 1 d . . . . .
O1 O 0.11636(11) 0.32069(4) 0.81070(7) 0.0220(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C6 1.5509(18) . ?
B1 C10 1.5802(18) . ?
B1 C19 1.5824(18) . ?
C1 N1 1.4421(17) . ?
C2 N1 1.4481(17) . ?
C3 C4 1.4082(18) . ?
C3 C8 1.4062(17) . ?
C3 N1 1.3713(16) . ?
C4 C5 1.3822(17) . ?
C5 C6 1.4045(17) . ?
C6 C7 1.4104(17) . ?
C7 C8 1.3859(17) . ?
C7 O1 1.3658(14) . ?
C9 O1 1.4217(15) . ?
C10 C11 1.4128(16) . ?
C10 C17 1.4149(16) . ?
C11 C12 1.5111(17) . ?
C11 C13 1.3897(18) . ?
C13 C14 1.3888(18) . ?
C14 C15 1.5060(18) . ?
C14 C16 1.3883(18) . ?
C16 C17 1.3902(18) . ?
C17 C18 1.5112(17) . ?
C19 C20 1.4066(17) . ?
C19 C26 1.4144(16) . ?
C20 C21 1.5131(16) . ?
C20 C22 1.3911(17) . ?
C22 C23 1.3917(17) . ?
C23 C24 1.5042(18) . ?
C23 C25 1.3859(18) . ?
C25 C26 1.3909(18) . ?
C26 C27 1.5107(17) . ?

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
C6 B1 C10 122.56(11) . . ?
C6 B1 C19 116.04(10) . . ?
C10 B1 C19 121.40(10) . . ?
C8 C3 C4 117.85(11) . . ?
N1 C3 C4 120.90(11) . . ?
N1 C3 C8 121.24(11) . . ?
C5 C4 C3 119.70(11) . . ?
C4 C5 C6 124.10(11) . . ?
C5 C6 B1 119.47(11) . . ?
C5 C6 C7 114.75(11) . . ?
C7 C6 B1 125.78(11) . . ?
C8 C7 C6 122.75(11) . . ?
O1 C7 C6 115.50(10) . . ?
O1 C7 C8 121.72(11) . . ?
C7 C8 C3 120.73(11) . . ?
C11 C10 B1 120.62(10) . . ?
C11 C10 C17 117.43(11) . . ?
C17 C10 B1 121.91(10) . . ?
C10 C11 C12 121.66(11) . . ?
C13 C11 C10 120.39(11) . . ?
C13 C11 C12 117.95(11) . . ?
C14 C13 C11 122.18(12) . . ?
C13 C14 C15 121.22(12) . . ?
C16 C14 C13 117.36(12) . . ?
C16 C14 C15 121.41(12) . . ?
C14 C16 C17 122.23(11) . . ?
C10 C17 C18 121.66(11) . . ?
C16 C17 C10 120.28(11) . . ?
C16 C17 C18 118.03(11) . . ?
C20 C19 B1 122.70(10) . . ?
C20 C19 C26 117.89(11) . . ?
C26 C19 B1 119.41(10) . . ?
C19 C20 C21 120.43(11) . . ?
C22 C20 C19 120.54(11) . . ?
C22 C20 C21 118.98(11) . . ?
C20 C22 C23 121.58(11) . . ?
C22 C23 C24 121.29(12) . . ?
C25 C23 C22 117.90(11) . . ?
C25 C23 C24 120.80(11) . . ?
C23 C25 C26 122.03(11) . . ?
C19 C26 C27 122.23(11) . . ?
C25 C26 C19 120.05(11) . . ?
C25 C26 C27 117.72(11) . . ?
C1 N1 C2 117.96(10) . . ?
C3 N1 C1 121.91(11) . . ?
C3 N1 C2 120.13(11) . . ?
C7 O1 C9 118.24(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 1.488
_oxdiff_exptl_absorpt_empirical_full_min 0.778
####################################################################### 
# 
# 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_ysw2-cp2-thf-100k
_database_code_depnum_ccdc_archive 'CCDC 2235715'
loop_
_audit_author_name
_audit_author_address
'Huangting Ding'
;YunNan University
China
;
_audit_update_record             
;
2023-01-12 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_audit_creation_date             2021-09-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C37 H36 B N'
_chemical_formula_sum            'C37 H36 B N'
_chemical_formula_weight         505.48
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.5510(2)
_cell_length_b                   11.2401(4)
_cell_length_c                   13.6050(3)
_cell_angle_alpha                75.998(2)
_cell_angle_beta                 84.321(2)
_cell_angle_gamma                80.055(2)
_cell_volume                     1393.36(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17725
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      29.0990
_cell_measurement_theta_min      1.5560
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.64a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.13
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32283
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.466
_diffrn_reflns_theta_min         1.545
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  85.00   0.50    0.40    --   10.29  62.00-122.00  188
  2  ω    -45.00 -20.00   0.50    0.40    --  -11.46  77.00  60.00   50
  3  ω     21.00  64.00   0.50    0.40    --  -11.46  77.00  60.00   86
  4  ω    -39.00  64.00   0.50    0.40    --  -11.46  57.00 -60.00  206
  5  ω    -20.00  52.00   0.50    0.40    --  -11.46  62.00-122.00  144
  6  ω    -54.00  40.00   0.50    0.40    --   10.29 -62.00  99.00  188
  7  ω    -75.00  21.00   0.50    0.40    --   10.29 -19.00 150.00  192
  8  ω     -8.00  34.00   0.50    0.40    --  -11.46 -99.00  90.00   84
  9  ω    -11.00  34.00   0.50    0.40    --  -11.46 -99.00 150.00   90
 10  ω      4.00  34.00   0.50    0.40    --  -11.46 -99.00 -30.00   60
 11  ω     -7.00  34.00   0.50    0.40    --  -11.46 -99.00 -60.00   82
 12  ω    -87.00 -35.00   0.50    0.40    --  -11.46 -62.00  99.00  104
 13  ω    -10.00  16.00   0.50    0.40    --  -11.46 -62.00  99.00   52
 14  ω     -1.00  33.00   0.50    0.40    --  -11.46 -99.00-120.00   68
 15  ω     -4.00  22.00   0.50    0.40    --   10.29 -99.00 -90.00   52
 16  ω    -11.00  15.00   0.50    0.40    --   10.29 -99.00-180.00   52
 17  ω     30.00  56.00   0.50    0.40    --   10.29 -99.00-180.00   52
 18  ω     30.00  56.00   0.50    0.40    --   10.29 -99.00 -90.00   52
 19  ω      6.00  56.00   0.50    0.40    --   10.29 -99.00  30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0488741000
_diffrn_orient_matrix_UB_12      0.0267611000
_diffrn_orient_matrix_UB_13      -0.0382565000
_diffrn_orient_matrix_UB_21      0.0024392000
_diffrn_orient_matrix_UB_22      0.0597418000
_diffrn_orient_matrix_UB_23      0.0078018000
_diffrn_orient_matrix_UB_31      0.0575374000
_diffrn_orient_matrix_UB_32      0.0068859000
_diffrn_orient_matrix_UB_33      -0.0370543000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5222
_reflns_number_total             6477
_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 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         6477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.101
_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)+(0.0573P)²+0.3353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1247
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C17(H17), C18(H18), C22(H22), C24(H24), C31(H31), C33(H33)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C35(H35A,H35B,
 H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.55907(11) 0.44485(11) 0.85260(8) 0.0273(2) Uani 1 1 d . . . . .
C1 C 0.63552(12) 0.41678(12) 0.93868(9) 0.0249(3) Uani 1 1 d . . . . .
C2 C 0.64498(15) 0.31140(13) 1.01765(11) 0.0348(3) Uani 1 1 d . . . . .
H2 H 0.596132 0.244697 1.017356 0.042 Uiso 1 1 calc R U . . .
C3 C 0.72740(17) 0.30688(16) 1.09625(11) 0.0430(4) Uani 1 1 d . . . . .
H3 H 0.734285 0.236313 1.151552 0.052 Uiso 1 1 calc R U . . .
C4 C 0.80063(16) 0.40309(17) 1.09650(11) 0.0438(4) Uani 1 1 d . . . . .
H4 H 0.857868 0.396605 1.151390 0.053 Uiso 1 1 calc R U . . .
C5 C 0.79189(14) 0.50802(15) 1.01852(11) 0.0353(3) Uani 1 1 d . . . . .
H5 H 0.842440 0.573475 1.019372 0.042 Uiso 1 1 calc R U . . .
C6 C 0.70726(12) 0.51637(12) 0.93811(9) 0.0250(3) Uani 1 1 d . . . . .
C7 C 0.67057(13) 0.60942(12) 0.84749(10) 0.0277(3) Uani 1 1 d . . . . .
C8 C 0.70191(17) 0.72917(14) 0.80811(12) 0.0406(4) Uani 1 1 d . . . . .
H8 H 0.761124 0.763424 0.842548 0.049 Uiso 1 1 calc R U . . .
C9 C 0.6458(2) 0.79642(16) 0.71901(13) 0.0549(5) Uani 1 1 d . . . . .
H9 H 0.666119 0.878203 0.691736 0.066 Uiso 1 1 calc R U . . .
C10 C 0.5597(2) 0.74694(18) 0.66786(12) 0.0578(5) Uani 1 1 d . . . . .
H10 H 0.523471 0.795421 0.605671 0.069 Uiso 1 1 calc R U . . .
C11 C 0.52522(17) 0.62882(17) 0.70500(11) 0.0443(4) Uani 1 1 d . . . . .
H11 H 0.466275 0.595490 0.669639 0.053 Uiso 1 1 calc R U . . .
C12 C 0.58058(13) 0.56121(13) 0.79624(10) 0.0286(3) Uani 1 1 d . . . . .
C13 C 0.47875(14) 0.36340(15) 0.82205(11) 0.0351(3) Uani 1 1 d . . . . .
H13A H 0.389861 0.412806 0.793284 0.042 Uiso 1 1 calc R U . . .
H13B H 0.451777 0.301205 0.882884 0.042 Uiso 1 1 calc R U . . .
C14 C 0.55927(13) 0.29584(12) 0.74418(9) 0.0248(3) Uani 1 1 d . . . . .
C15 C 0.70639(13) 0.28921(13) 0.72902(10) 0.0303(3) Uani 1 1 d . . . . .
H15 H 0.755508 0.327304 0.767420 0.036 Uiso 1 1 calc R U . . .
C16 C 0.78235(13) 0.22811(13) 0.65899(10) 0.0297(3) Uani 1 1 d . . . . .
H16 H 0.883052 0.222468 0.651004 0.036 Uiso 1 1 calc R U . . .
C17 C 0.71189(14) 0.17538(12) 0.60074(10) 0.0285(3) Uani 1 1 d . . . . .
H17 H 0.763476 0.133769 0.552233 0.034 Uiso 1 1 calc R U . . .
C18 C 0.56483(13) 0.18376(12) 0.61377(9) 0.0250(3) Uani 1 1 d . . . . .
H18 H 0.516502 0.149754 0.571880 0.030 Uiso 1 1 calc R U . . .
C19 C 0.48529(12) 0.24085(11) 0.68682(9) 0.0211(2) Uani 1 1 d . . . . .
C20 C 0.25388(12) 0.18534(11) 0.81559(9) 0.0216(2) Uani 1 1 d . . . . .
C21 C 0.31736(13) 0.08028(12) 0.88613(9) 0.0250(3) Uani 1 1 d . . . . .
C22 C 0.25035(14) 0.04352(12) 0.98177(9) 0.0275(3) Uani 1 1 d . . . . .
H22 H 0.293019 -0.028743 1.027364 0.033 Uiso 1 1 calc R U . . .
C23 C 0.12366(13) 0.10859(12) 1.01279(9) 0.0259(3) Uani 1 1 d . . . . .
C24 C 0.06275(13) 0.21319(12) 0.94461(9) 0.0255(3) Uani 1 1 d . . . . .
H24 H -0.023183 0.260017 0.964829 0.031 Uiso 1 1 calc R U . . .
C25 C 0.12430(12) 0.25147(11) 0.84716(9) 0.0223(3) Uani 1 1 d . . . . .
C26 C 0.45408(14) 0.00102(14) 0.86045(10) 0.0338(3) Uani 1 1 d . . . . .
H26A H 0.436789 -0.044622 0.811040 0.051 Uiso 1 1 calc R U . . .
H26B H 0.488042 -0.057921 0.922203 0.051 Uiso 1 1 calc R U . . .
H26C H 0.526140 0.054155 0.831429 0.051 Uiso 1 1 calc R U . . .
C27 C 0.05462(16) 0.06620(14) 1.11723(10) 0.0338(3) Uani 1 1 d . . . . .
H27A H -0.015748 0.013570 1.113850 0.051 Uiso 1 1 calc R U . . .
H27B H 0.007249 0.138684 1.142223 0.051 Uiso 1 1 calc R U . . .
H27C H 0.127518 0.018812 1.163453 0.051 Uiso 1 1 calc R U . . .
C28 C 0.05358(13) 0.36874(12) 0.77949(10) 0.0282(3) Uani 1 1 d . . . . .
H28A H 0.121122 0.427969 0.758799 0.042 Uiso 1 1 calc R U . . .
H28B H -0.029617 0.405141 0.816485 0.042 Uiso 1 1 calc R U . . .
H28C H 0.023227 0.349379 0.719156 0.042 Uiso 1 1 calc R U . . .
C29 C 0.23720(12) 0.23840(11) 0.60875(9) 0.0204(2) Uani 1 1 d . . . . .
C30 C 0.18254(12) 0.13677(11) 0.59138(9) 0.0212(2) Uani 1 1 d . . . . .
C31 C 0.10438(12) 0.15188(12) 0.50699(9) 0.0232(3) Uani 1 1 d . . . . .
H31 H 0.070805 0.082012 0.495295 0.028 Uiso 1 1 calc R U . . .
C32 C 0.07399(13) 0.26559(12) 0.43954(9) 0.0248(3) Uani 1 1 d . . . . .
C33 C 0.12918(13) 0.36511(12) 0.45569(9) 0.0251(3) Uani 1 1 d . . . . .
H33 H 0.109508 0.443827 0.410132 0.030 Uiso 1 1 calc R U . . .
C34 C 0.21276(13) 0.35263(11) 0.53702(9) 0.0224(3) Uani 1 1 d . . . . .
C35 C 0.21228(15) 0.00944(12) 0.66066(10) 0.0294(3) Uani 1 1 d . . . . .
H35A H 0.315151 -0.019473 0.659477 0.044 Uiso 1 1 calc R U . . .
H35B H 0.164419 -0.048330 0.637465 0.044 Uiso 1 1 calc R U . . .
H35C H 0.176574 0.013445 0.730020 0.044 Uiso 1 1 calc R U . . .
C36 C -0.01473(15) 0.28001(14) 0.35047(10) 0.0324(3) Uani 1 1 d . . . . .
H36A H 0.007758 0.205123 0.323518 0.049 Uiso 1 1 calc R U . . .
H36B H 0.006346 0.351990 0.297462 0.049 Uiso 1 1 calc R U . . .
H36C H -0.115952 0.292282 0.372541 0.049 Uiso 1 1 calc R U . . .
C37 C 0.27473(15) 0.46430(12) 0.54560(10) 0.0295(3) Uani 1 1 d . . . . .
H37A H 0.281252 0.462664 0.617362 0.044 Uiso 1 1 calc R U . . .
H37B H 0.213168 0.540261 0.513755 0.044 Uiso 1 1 calc R U . . .
H37C H 0.369974 0.462443 0.511251 0.044 Uiso 1 1 calc R U . . .
B1 B 0.32391(14) 0.22456(12) 0.70484(10) 0.0207(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
N1 C1 1.3838(16) . ?
N1 C12 1.3846(18) . ?
N1 C13 1.4454(16) . ?
C1 C2 1.390(2) . ?
C1 C6 1.4080(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3993(18) . ?
C6 C7 1.4393(19) . ?
C7 C8 1.395(2) . ?
C7 C12 1.4075(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.369(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5221(17) . ?
C14 C15 1.3916(17) . ?
C14 C19 1.4084(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3833(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3793(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3879(17) . ?
C18 H18 0.9500 . ?
C18 C19 1.4026(16) . ?
C19 B1 1.5718(17) . ?
C20 C21 1.4151(17) . ?
C20 C25 1.4143(17) . ?
C20 B1 1.5789(17) . ?
C21 C22 1.3928(17) . ?
C21 C26 1.5098(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.3855(18) . ?
C23 C24 1.3871(19) . ?
C23 C27 1.5088(17) . ?
C24 H24 0.9500 . ?
C24 C25 1.3948(17) . ?
C25 C28 1.5065(18) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.4122(16) . ?
C29 C34 1.4109(17) . ?
C29 B1 1.5781(17) . ?
C30 C31 1.3913(17) . ?
C30 C35 1.5090(18) . ?
C31 H31 0.9500 . ?
C31 C32 1.3845(18) . ?
C32 C33 1.3867(18) . ?
C32 C36 1.5078(17) . ?
C33 H33 0.9500 . ?
C33 C34 1.3937(17) . ?
C34 C37 1.5101(17) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 108.54(10) . . ?
C1 N1 C13 126.09(12) . . ?
C12 N1 C13 125.21(12) . . ?
N1 C1 C2 129.14(12) . . ?
N1 C1 C6 109.13(11) . . ?
C2 C1 C6 121.72(12) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.81(14) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.42(15) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.19(14) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.83(14) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 106.54(11) . . ?
C5 C6 C1 119.01(13) . . ?
C5 C6 C7 134.44(13) . . ?
C8 C7 C6 133.45(13) . . ?
C8 C7 C12 119.70(13) . . ?
C12 C7 C6 106.81(11) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.83(16) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 121.01(17) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.84(16) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 121.4 . . ?
C10 C11 C12 117.12(16) . . ?
C12 C11 H11 121.4 . . ?
N1 C12 C7 108.96(11) . . ?
N1 C12 C11 129.56(14) . . ?
C11 C12 C7 121.47(14) . . ?
N1 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
N1 C13 C14 113.71(10) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C15 C14 C13 119.89(11) . . ?
C15 C14 C19 119.86(11) . . ?
C19 C14 C13 120.25(10) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.13(12) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.01(12) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.29(11) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.0 . . ?
C17 C18 C19 122.10(12) . . ?
C19 C18 H18 119.0 . . ?
C14 C19 B1 125.88(10) . . ?
C18 C19 C14 117.54(11) . . ?
C18 C19 B1 116.23(10) . . ?
C21 C20 B1 120.84(10) . . ?
C25 C20 C21 117.61(11) . . ?
C25 C20 B1 121.53(11) . . ?
C20 C21 C26 122.40(11) . . ?
C22 C21 C20 120.00(11) . . ?
C22 C21 C26 117.54(12) . . ?
C21 C22 H22 118.8 . . ?
C23 C22 C21 122.34(12) . . ?
C23 C22 H22 118.8 . . ?
C22 C23 C24 117.79(11) . . ?
C22 C23 C27 120.80(12) . . ?
C24 C23 C27 121.41(12) . . ?
C23 C24 H24 119.1 . . ?
C23 C24 C25 121.76(12) . . ?
C25 C24 H24 119.1 . . ?
C20 C25 C28 121.31(11) . . ?
C24 C25 C20 120.46(11) . . ?
C24 C25 C28 118.13(11) . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 B1 121.13(11) . . ?
C34 C29 C30 117.88(11) . . ?
C34 C29 B1 120.98(10) . . ?
C29 C30 C35 121.17(11) . . ?
C31 C30 C29 120.03(11) . . ?
C31 C30 C35 118.76(11) . . ?
C30 C31 H31 119.0 . . ?
C32 C31 C30 122.05(11) . . ?
C32 C31 H31 119.0 . . ?
C31 C32 C33 117.98(11) . . ?
C31 C32 C36 120.86(11) . . ?
C33 C32 C36 121.15(12) . . ?
C32 C33 H33 119.2 . . ?
C32 C33 C34 121.70(12) . . ?
C34 C33 H33 119.2 . . ?
C29 C34 C37 121.72(11) . . ?
C33 C34 C29 120.21(11) . . ?
C33 C34 C37 118.07(11) . . ?
C30 C35 H35A 109.5 . . ?
C30 C35 H35B 109.5 . . ?
C30 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C32 C36 H36A 109.5 . . ?
C32 C36 H36B 109.5 . . ?
C32 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
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 . . ?
C19 B1 C20 121.07(10) . . ?
C19 B1 C29 117.85(10) . . ?
C29 B1 C20 120.92(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -178.95(12) . . . . ?
N1 C1 C6 C5 -179.93(10) . . . . ?
N1 C1 C6 C7 0.63(13) . . . . ?
N1 C13 C14 C15 16.8(2) . . . . ?
N1 C13 C14 C19 -162.65(12) . . . . ?
C1 N1 C12 C7 -0.82(13) . . . . ?
C1 N1 C12 C11 -179.31(13) . . . . ?
C1 N1 C13 C14 -97.38(15) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C1 C6 C7 C8 176.22(13) . . . . ?
C1 C6 C7 C12 -1.11(13) . . . . ?
C2 C1 C6 C5 0.96(18) . . . . ?
C2 C1 C6 C7 -178.49(11) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C1 -0.91(18) . . . . ?
C4 C5 C6 C7 178.34(13) . . . . ?
C5 C6 C7 C8 -3.1(2) . . . . ?
C5 C6 C7 C12 179.58(13) . . . . ?
C6 C1 C2 C3 -0.03(19) . . . . ?
C6 C7 C8 C9 -178.17(14) . . . . ?
C6 C7 C12 N1 1.20(13) . . . . ?
C6 C7 C12 C11 179.83(12) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C8 C7 C12 N1 -176.57(11) . . . . ?
C8 C7 C12 C11 2.07(19) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 N1 176.85(13) . . . . ?
C10 C11 C12 C7 -1.48(19) . . . . ?
C12 N1 C1 C2 179.13(12) . . . . ?
C12 N1 C1 C6 0.10(13) . . . . ?
C12 N1 C13 C14 77.61(17) . . . . ?
C12 C7 C8 C9 -1.12(19) . . . . ?
C13 N1 C1 C2 -5.2(2) . . . . ?
C13 N1 C1 C6 175.79(11) . . . . ?
C13 N1 C12 C7 -176.55(11) . . . . ?
C13 N1 C12 C11 5.0(2) . . . . ?
C13 C14 C15 C16 179.80(13) . . . . ?
C13 C14 C19 C18 177.80(12) . . . . ?
C13 C14 C19 B1 -9.3(2) . . . . ?
C14 C15 C16 C17 1.8(2) . . . . ?
C14 C19 B1 C20 -40.47(18) . . . . ?
C14 C19 B1 C29 144.21(12) . . . . ?
C15 C14 C19 C18 -1.70(18) . . . . ?
C15 C14 C19 B1 171.22(12) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C16 C17 C18 C19 -2.1(2) . . . . ?
C17 C18 C19 C14 3.13(18) . . . . ?
C17 C18 C19 B1 -170.47(12) . . . . ?
C18 C19 B1 C20 132.53(12) . . . . ?
C18 C19 B1 C29 -42.79(15) . . . . ?
C19 C14 C15 C16 -0.7(2) . . . . ?
C20 C21 C22 C23 -1.96(19) . . . . ?
C21 C20 C25 C24 -0.01(17) . . . . ?
C21 C20 C25 C28 176.32(11) . . . . ?
C21 C20 B1 C19 -51.40(16) . . . . ?
C21 C20 B1 C29 123.77(12) . . . . ?
C21 C22 C23 C24 0.53(18) . . . . ?
C21 C22 C23 C27 -179.70(12) . . . . ?
C22 C23 C24 C25 1.17(18) . . . . ?
C23 C24 C25 C20 -1.43(18) . . . . ?
C23 C24 C25 C28 -177.87(11) . . . . ?
C25 C20 C21 C22 1.64(17) . . . . ?
C25 C20 C21 C26 178.80(11) . . . . ?
C25 C20 B1 C19 130.21(12) . . . . ?
C25 C20 B1 C29 -54.61(16) . . . . ?
C26 C21 C22 C23 -179.25(12) . . . . ?
C27 C23 C24 C25 -178.60(11) . . . . ?
C29 C30 C31 C32 -1.88(17) . . . . ?
C30 C29 C34 C33 4.11(17) . . . . ?
C30 C29 C34 C37 -176.14(11) . . . . ?
C30 C29 B1 C19 114.87(12) . . . . ?
C30 C29 B1 C20 -60.46(15) . . . . ?
C30 C31 C32 C33 2.70(18) . . . . ?
C30 C31 C32 C36 -178.14(11) . . . . ?
C31 C32 C33 C34 -0.06(18) . . . . ?
C32 C33 C34 C29 -3.38(18) . . . . ?
C32 C33 C34 C37 176.86(11) . . . . ?
C34 C29 C30 C31 -1.56(16) . . . . ?
C34 C29 C30 C35 175.91(11) . . . . ?
C34 C29 B1 C19 -64.65(15) . . . . ?
C34 C29 B1 C20 120.02(12) . . . . ?
C35 C30 C31 C32 -179.41(11) . . . . ?
C36 C32 C33 C34 -179.21(11) . . . . ?
B1 C20 C21 C22 -176.80(11) . . . . ?
B1 C20 C21 C26 0.35(18) . . . . ?
B1 C20 C25 C24 178.43(10) . . . . ?
B1 C20 C25 C28 -5.25(17) . . . . ?
B1 C29 C30 C31 178.91(10) . . . . ?
B1 C29 C30 C35 -3.62(17) . . . . ?
B1 C29 C34 C33 -176.36(11) . . . . ?
B1 C29 C34 C37 3.40(17) . . . . ?

_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 1.232
_oxdiff_exptl_absorpt_empirical_full_min 0.806
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2235713'
loop_
_audit_author_name
_audit_author_address
'Huangting Ding'
;YunNan University
China
;
_audit_update_record             
;
2023-01-12 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_audit_creation_date             2021-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C D Cl3 , C39 H41 B N2'
_chemical_formula_sum            ' C D Cl3 , C39 H41 B N2'
_chemical_formula_weight         668.92
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5734(3)
_cell_length_b                   14.7640(5)
_cell_length_c                   15.2580(6)
_cell_angle_alpha                68.839(4)
_cell_angle_beta                 87.111(3)
_cell_angle_gamma                78.724(3)
_cell_volume                     1765.90(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12693
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0920
_cell_measurement_theta_min      1.6650
_shelx_estimated_absorpt_T_max   1.00000
_shelx_estimated_absorpt_T_min   0.83623
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.813
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23874
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.511
_diffrn_reflns_theta_min         1.507
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.813
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6077
_reflns_number_total             9855
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.461
_refine_diff_density_min         -1.123
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         8016
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.1117
_refine_ls_restrained_S_all      1.077
_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)+(0.1126P)²+14.6191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3332
_refine_ls_wR_factor_ref         0.3422
_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:
 C21(D21)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20a,H20b)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00E(H00E), C00F(H00F), C00L(H00L), C00N(H00N),
 C00O(H00O), C00P(H00P), C00V(H00V), C010(H010), C011(H011), C012(H012),
 C013(H013), C014(H014), C016(H016)
2.d Idealised Me refined as rotating group:
 C00S(H00b,H00c,H00d), C00U(H00g,H00h,H00i), C00W(H00j,H00k,H00m), C00Y(H00q,
 H00r,H00s), C00Z(H00t,H00u,H00w), C015(H01a,H01b,H01c), C017(H01d,H01e,H01f),
 C019(H01g,H01h,H01i)
;
_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
Cl3 Cl 0.4558(2) 0.25616(13) 0.84175(15) 0.0535(5) Uani 1 1 d . . . . .
Cl2 Cl 0.2255(3) 0.17322(14) 0.97468(13) 0.0538(5) Uani 1 1 d . . . . .
Cl1 Cl 0.1954(3) 0.19992(17) 0.77805(15) 0.0660(6) Uani 1 1 d . . . . .
N004 N 0.4178(5) 0.8606(3) 0.4902(3) 0.0228(9) Uani 1 1 d . . . . .
N005 N 0.7277(5) 0.5279(4) 0.5209(3) 0.0277(10) Uani 1 1 d . . . . .
C006 C 0.3927(6) 0.7331(4) 0.8288(4) 0.0214(10) Uani 1 1 d . . . . .
C007 C -0.1072(6) 0.4994(4) 0.7738(4) 0.0241(11) Uani 1 1 d . . . . .
H007 H -0.188872 0.500101 0.735537 0.029 Uiso 1 1 calc R . . . .
C008 C -0.0071(6) 0.5676(4) 0.7383(4) 0.0208(10) Uani 1 1 d . . . . .
C009 C 0.1171(6) 0.5690(4) 0.7947(4) 0.0200(10) Uani 1 1 d . . . . .
C00A C 0.0341(6) 0.4319(4) 0.9206(4) 0.0270(11) Uani 1 1 d . . . . .
H00A H 0.047114 0.387403 0.982287 0.032 Uiso 1 1 calc R . . . .
C00B C 0.1374(6) 0.4981(4) 0.8866(4) 0.0229(10) Uani 1 1 d . . . . .
C00C C 0.6029(5) 0.5569(4) 0.5707(4) 0.0219(10) Uani 1 1 d . . . . .
C00D C 0.4227(5) 0.6898(4) 0.6038(4) 0.0202(10) Uani 1 1 d . . . . .
C00E C 0.1149(7) 0.8505(4) 0.8597(4) 0.0259(11) Uani 1 1 d . . . . .
H00E H 0.022629 0.891466 0.867895 0.031 Uiso 1 1 calc R . . . .
C00F C 0.5400(6) 0.6578(4) 0.5507(4) 0.0228(10) Uani 1 1 d . . . . .
H00F H 0.578942 0.704537 0.499936 0.027 Uiso 1 1 calc R . . . .
C00G C 0.2446(6) 0.7251(4) 0.7963(3) 0.0201(10) Uani 1 1 d . . . . .
C00H C 0.5606(6) 0.8945(4) 0.4769(4) 0.0235(10) Uani 1 1 d . . . . .
C00I C 0.1053(6) 0.7875(4) 0.8124(4) 0.0219(10) Uani 1 1 d . . . . .
C00J C 0.3539(6) 0.6218(4) 0.6792(4) 0.0200(10) Uani 1 1 d . . . . .
C00K C 0.4476(6) 0.9318(4) 0.3323(4) 0.0250(11) Uani 1 1 d . . . . .
C00L C 0.5339(6) 0.4886(4) 0.6436(4) 0.0240(11) Uani 1 1 d . . . . .
H00L H 0.570852 0.421189 0.658183 0.029 Uiso 1 1 calc R . . . .
C00M C 0.5827(6) 0.9398(4) 0.3799(4) 0.0242(11) Uani 1 1 d . . . . .
C00N C 0.4118(6) 0.5207(4) 0.6938(4) 0.0227(10) Uani 1 1 d . . . . .
H00N H 0.365044 0.473549 0.739753 0.027 Uiso 1 1 calc R . . . .
C00O C 0.3951(6) 0.7953(4) 0.8788(4) 0.0261(11) Uani 1 1 d . . . . .
H00O H 0.492144 0.797231 0.901987 0.031 Uiso 1 1 calc R . . . .
C00P C 0.6708(7) 0.8879(4) 0.5438(4) 0.0272(11) Uani 1 1 d . . . . .
H00P H 0.655474 0.857381 0.607701 0.033 Uiso 1 1 calc R . . . .
C00Q C 0.3517(6) 0.8802(4) 0.4032(4) 0.0246(11) Uani 1 1 d . . . . .
C20 C 0.3618(6) 0.8004(4) 0.5796(4) 0.0248(11) Uani 1 1 d . . . . .
H20A H 0.246436 0.813378 0.577866 0.030 Uiso 1 1 calc R . . . .
H20B H 0.395805 0.819725 0.628922 0.030 Uiso 1 1 calc R . . . .
C00S C -0.0421(6) 0.6417(4) 0.6400(4) 0.0257(11) Uani 1 1 d . . . . .
H00B H -0.070950 0.609471 0.600389 0.039 Uiso 1 1 calc GR . . . .
H00C H 0.050671 0.669195 0.615994 0.039 Uiso 1 1 calc GR . . . .
H00D H -0.128443 0.693668 0.640990 0.039 Uiso 1 1 calc GR . . . .
C00T C -0.0882(6) 0.4304(4) 0.8648(4) 0.0277(11) Uani 1 1 d . . . . .
C00U C -0.0571(6) 0.7874(4) 0.7783(4) 0.0284(12) Uani 1 1 d . . . . .
H00G H -0.088721 0.725781 0.813868 0.043 Uiso 1 1 calc GR . . . .
H00H H -0.052917 0.795558 0.712941 0.043 Uiso 1 1 calc GR . . . .
H00I H -0.132842 0.840901 0.786368 0.043 Uiso 1 1 calc GR . . . .
C00V C 0.4029(7) 0.9611(4) 0.2384(4) 0.0308(12) Uani 1 1 d . . . . .
H00V H 0.465296 0.995310 0.191163 0.037 Uiso 1 1 calc R . . . .
C00W C 0.2755(7) 0.4894(5) 0.9486(4) 0.0302(12) Uani 1 1 d . . . . .
H00J H 0.368187 0.449589 0.933937 0.045 Uiso 1 1 calc GR . . . .
H00K H 0.249899 0.459069 1.013304 0.045 Uiso 1 1 calc GR . . . .
H00M H 0.296234 0.554131 0.937891 0.045 Uiso 1 1 calc GR . . . .
C00X C 0.2590(7) 0.8543(4) 0.8953(4) 0.0270(11) Uani 1 1 d . . . . .
C00Y C 0.5507(6) 0.6736(4) 0.8151(4) 0.0277(11) Uani 1 1 d . . . . .
H00Q H 0.542910 0.605104 0.834461 0.042 Uiso 1 1 calc GR . . . .
H00R H 0.631676 0.680427 0.852175 0.042 Uiso 1 1 calc GR . . . .
H00S H 0.577574 0.697334 0.749932 0.042 Uiso 1 1 calc GR . . . .
C00Z C 0.7720(7) 0.5976(5) 0.4334(4) 0.0311(12) Uani 1 1 d . . . . .
H00T H 0.680420 0.627186 0.392092 0.047 Uiso 1 1 calc GR . . . .
H00U H 0.852686 0.563535 0.404312 0.047 Uiso 1 1 calc GR . . . .
H00W H 0.812372 0.648154 0.445696 0.047 Uiso 1 1 calc GR . . . .
C010 C 0.7195(7) 0.9803(4) 0.3492(4) 0.0308(12) Uani 1 1 d . . . . .
H010 H 0.736204 1.010727 0.285434 0.037 Uiso 1 1 calc R . . . .
C011 C 0.2646(7) 0.9388(5) 0.2161(5) 0.0366(14) Uani 1 1 d . . . . .
H011 H 0.233614 0.958136 0.153476 0.044 Uiso 1 1 calc R . . . .
C012 C 0.2109(7) 0.8575(4) 0.3806(5) 0.0318(12) Uani 1 1 d . . . . .
H012 H 0.147252 0.823675 0.427292 0.038 Uiso 1 1 calc R . . . .
C013 C 0.8046(7) 0.9289(4) 0.5110(5) 0.0332(13) Uani 1 1 d . . . . .
H013 H 0.880272 0.926124 0.553921 0.040 Uiso 1 1 calc R . . . .
C014 C 0.1706(7) 0.8872(5) 0.2870(5) 0.0397(15) Uani 1 1 d . . . . .
H014 H 0.078235 0.872632 0.270293 0.048 Uiso 1 1 calc R . . . .
C015 C 0.7867(7) 0.4232(5) 0.5422(4) 0.0324(13) Uani 1 1 d . . . . .
H01A H 0.812641 0.391363 0.608051 0.049 Uiso 1 1 calc GR . . . .
H01B H 0.880214 0.414333 0.506520 0.049 Uiso 1 1 calc GR . . . .
H01C H 0.706415 0.394481 0.525954 0.049 Uiso 1 1 calc GR . . . .
C016 C 0.8280(7) 0.9740(4) 0.4152(5) 0.0340(13) Uani 1 1 d . . . . .
H016 H 0.919166 1.000462 0.395569 0.041 Uiso 1 1 calc R . . . .
C017 C -0.1984(8) 0.3570(5) 0.9016(5) 0.0401(15) Uani 1 1 d . . . . .
H01D H -0.306332 0.390577 0.884454 0.060 Uiso 1 1 calc GR . . . .
H01E H -0.187457 0.327487 0.968785 0.060 Uiso 1 1 calc GR . . . .
H01F H -0.171294 0.306450 0.874782 0.060 Uiso 1 1 calc GR . . . .
C21 C 0.2544(7) 0.2479(5) 0.8585(5) 0.0368(14) Uani 1 1 d . . . . .
D21 D 0.191233 0.314350 0.846073 0.044 Uiso 1 1 calc R . . . .
C019 C 0.2620(9) 0.9199(5) 0.9514(5) 0.0398(14) Uani 1 1 d . . . . .
H01G H 0.212395 0.986536 0.915093 0.060 Uiso 1 1 calc GR . . . .
H01H H 0.370194 0.918414 0.966181 0.060 Uiso 1 1 calc GR . . . .
H01I H 0.205250 0.896501 1.008514 0.060 Uiso 1 1 calc GR . . . .
B19 B 0.2367(7) 0.6434(4) 0.7540(4) 0.0212(11) 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
Cl3 C21 1.754(6) . ?
Cl2 C21 1.753(7) . ?
Cl1 C21 1.759(7) . ?
N004 C00H 1.389(7) . ?
N004 C00Q 1.378(7) . ?
N004 C20 1.452(7) . ?
N005 C00C 1.370(6) . ?
N005 C00Z 1.448(8) . ?
N005 C015 1.450(7) . ?
C006 C00G 1.427(7) . ?
C006 C00O 1.392(8) . ?
C006 C00Y 1.513(7) . ?
C007 H007 0.9300 . ?
C007 C008 1.393(7) . ?
C007 C00T 1.389(8) . ?
C008 C009 1.411(7) . ?
C008 C00S 1.506(7) . ?
C009 C00B 1.409(7) . ?
C009 B19 1.589(7) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.391(7) . ?
C00A C00T 1.392(8) . ?
C00B C00W 1.510(7) . ?
C00C C00F 1.406(7) . ?
C00C C00L 1.400(8) . ?
C00D C00F 1.379(7) . ?
C00D C00J 1.417(7) . ?
C00D C20 1.526(7) . ?
C00E H00E 0.9300 . ?
C00E C00I 1.382(8) . ?
C00E C00X 1.394(8) . ?
C00F H00F 0.9300 . ?
C00G C00I 1.429(7) . ?
C00G B19 1.574(8) . ?
C00H C00M 1.406(8) . ?
C00H C00P 1.391(8) . ?
C00I C00U 1.511(7) . ?
C00J C00N 1.416(7) . ?
C00J B19 1.561(7) . ?
C00K C00M 1.443(8) . ?
C00K C00Q 1.409(7) . ?
C00K C00V 1.390(8) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.376(7) . ?
C00M C010 1.403(7) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00O C00X 1.384(8) . ?
C00P H00P 0.9300 . ?
C00P C013 1.388(8) . ?
C00Q C012 1.404(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C00S H00B 0.9600 . ?
C00S H00C 0.9600 . ?
C00S H00D 0.9600 . ?
C00T C017 1.513(8) . ?
C00U H00G 0.9600 . ?
C00U H00H 0.9600 . ?
C00U H00I 0.9600 . ?
C00V H00V 0.9300 . ?
C00V C011 1.380(9) . ?
C00W H00J 0.9600 . ?
C00W H00K 0.9600 . ?
C00W H00M 0.9600 . ?
C00X C019 1.510(8) . ?
C00Y H00Q 0.9600 . ?
C00Y H00R 0.9600 . ?
C00Y H00S 0.9600 . ?
C00Z H00T 0.9600 . ?
C00Z H00U 0.9600 . ?
C00Z H00W 0.9600 . ?
C010 H010 0.9300 . ?
C010 C016 1.372(9) . ?
C011 H011 0.9300 . ?
C011 C014 1.398(10) . ?
C012 H012 0.9300 . ?
C012 C014 1.376(9) . ?
C013 H013 0.9300 . ?
C013 C016 1.393(9) . ?
C014 H014 0.9300 . ?
C015 H01A 0.9600 . ?
C015 H01B 0.9600 . ?
C015 H01C 0.9600 . ?
C016 H016 0.9300 . ?
C017 H01D 0.9600 . ?
C017 H01E 0.9600 . ?
C017 H01F 0.9600 . ?
C21 D21 0.9800 . ?
C019 H01G 0.9600 . ?
C019 H01H 0.9600 . ?
C019 H01I 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
C00H N004 C20 125.4(4) . . ?
C00Q N004 C00H 108.3(4) . . ?
C00Q N004 C20 125.6(4) . . ?
C00C N005 C00Z 120.4(5) . . ?
C00C N005 C015 119.0(5) . . ?
C00Z N005 C015 118.6(5) . . ?
C00G C006 C00Y 123.1(5) . . ?
C00O C006 C00G 119.8(5) . . ?
C00O C006 C00Y 117.1(5) . . ?
C008 C007 H007 119.1 . . ?
C00T C007 H007 119.1 . . ?
C00T C007 C008 121.7(5) . . ?
C007 C008 C009 120.5(5) . . ?
C007 C008 C00S 117.4(5) . . ?
C009 C008 C00S 122.0(5) . . ?
C008 C009 B19 121.1(4) . . ?
C00B C009 C008 117.6(5) . . ?
C00B C009 B19 121.2(4) . . ?
C00B C00A H00A 119.1 . . ?
C00B C00A C00T 121.7(5) . . ?
C00T C00A H00A 119.1 . . ?
C009 C00B C00W 120.8(5) . . ?
C00A C00B C009 120.6(5) . . ?
C00A C00B C00W 118.6(5) . . ?
N005 C00C C00F 120.6(5) . . ?
N005 C00C C00L 122.1(5) . . ?
C00L C00C C00F 117.2(4) . . ?
C00F C00D C00J 121.3(5) . . ?
C00F C00D C20 119.6(5) . . ?
C00J C00D C20 119.1(4) . . ?
C00I C00E H00E 119.1 . . ?
C00I C00E C00X 121.8(5) . . ?
C00X C00E H00E 119.1 . . ?
C00C C00F H00F 118.9 . . ?
C00D C00F C00C 122.2(5) . . ?
C00D C00F H00F 118.9 . . ?
C006 C00G C00I 116.9(5) . . ?
C006 C00G B19 120.4(4) . . ?
C00I C00G B19 122.4(4) . . ?
N004 C00H C00M 109.0(5) . . ?
N004 C00H C00P 128.9(5) . . ?
C00P C00H C00M 122.1(5) . . ?
C00E C00I C00G 120.9(5) . . ?
C00E C00I C00U 117.8(5) . . ?
C00G C00I C00U 121.4(5) . . ?
C00D C00J B19 128.3(5) . . ?
C00N C00J C00D 115.4(4) . . ?
C00N C00J B19 116.0(5) . . ?
C00Q C00K C00M 106.2(5) . . ?
C00V C00K C00M 133.9(5) . . ?
C00V C00K C00Q 119.9(5) . . ?
C00C C00L H00L 119.8 . . ?
C00N C00L C00C 120.4(5) . . ?
C00N C00L H00L 119.8 . . ?
C00H C00M C00K 106.8(5) . . ?
C010 C00M C00H 119.3(5) . . ?
C010 C00M C00K 133.8(5) . . ?
C00J C00N H00N 118.3 . . ?
C00L C00N C00J 123.3(5) . . ?
C00L C00N H00N 118.3 . . ?
C006 C00O H00O 118.6 . . ?
C00X C00O C006 122.7(5) . . ?
C00X C00O H00O 118.6 . . ?
C00H C00P H00P 121.4 . . ?
C013 C00P C00H 117.1(5) . . ?
C013 C00P H00P 121.4 . . ?
N004 C00Q C00K 109.6(5) . . ?
N004 C00Q C012 129.4(5) . . ?
C012 C00Q C00K 121.1(5) . . ?
N004 C20 C00D 113.1(4) . . ?
N004 C20 H20A 109.0 . . ?
N004 C20 H20B 109.0 . . ?
C00D C20 H20A 109.0 . . ?
C00D C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C008 C00S H00B 109.5 . . ?
C008 C00S H00C 109.5 . . ?
C008 C00S H00D 109.5 . . ?
H00B C00S H00C 109.5 . . ?
H00B C00S H00D 109.5 . . ?
H00C C00S H00D 109.5 . . ?
C007 C00T C00A 117.8(5) . . ?
C007 C00T C017 120.7(5) . . ?
C00A C00T C017 121.6(5) . . ?
C00I C00U H00G 109.5 . . ?
C00I C00U H00H 109.5 . . ?
C00I C00U H00I 109.5 . . ?
H00G C00U H00H 109.5 . . ?
H00G C00U H00I 109.5 . . ?
H00H C00U H00I 109.5 . . ?
C00K C00V H00V 120.4 . . ?
C011 C00V C00K 119.1(6) . . ?
C011 C00V H00V 120.4 . . ?
C00B C00W H00J 109.5 . . ?
C00B C00W H00K 109.5 . . ?
C00B C00W H00M 109.5 . . ?
H00J C00W H00K 109.5 . . ?
H00J C00W H00M 109.5 . . ?
H00K C00W H00M 109.5 . . ?
C00E C00X C019 119.8(5) . . ?
C00O C00X C00E 117.7(5) . . ?
C00O C00X C019 122.4(5) . . ?
C006 C00Y H00Q 109.5 . . ?
C006 C00Y H00R 109.5 . . ?
C006 C00Y H00S 109.5 . . ?
H00Q C00Y H00R 109.5 . . ?
H00Q C00Y H00S 109.5 . . ?
H00R C00Y H00S 109.5 . . ?
N005 C00Z H00T 109.5 . . ?
N005 C00Z H00U 109.5 . . ?
N005 C00Z H00W 109.5 . . ?
H00T C00Z H00U 109.5 . . ?
H00T C00Z H00W 109.5 . . ?
H00U C00Z H00W 109.5 . . ?
C00M C010 H010 120.7 . . ?
C016 C010 C00M 118.6(6) . . ?
C016 C010 H010 120.7 . . ?
C00V C011 H011 119.7 . . ?
C00V C011 C014 120.6(6) . . ?
C014 C011 H011 119.7 . . ?
C00Q C012 H012 121.2 . . ?
C014 C012 C00Q 117.5(6) . . ?
C014 C012 H012 121.2 . . ?
C00P C013 H013 119.3 . . ?
C00P C013 C016 121.4(6) . . ?
C016 C013 H013 119.3 . . ?
C011 C014 H014 119.1 . . ?
C012 C014 C011 121.8(6) . . ?
C012 C014 H014 119.1 . . ?
N005 C015 H01A 109.5 . . ?
N005 C015 H01B 109.5 . . ?
N005 C015 H01C 109.5 . . ?
H01A C015 H01B 109.5 . . ?
H01A C015 H01C 109.5 . . ?
H01B C015 H01C 109.5 . . ?
C010 C016 C013 121.5(5) . . ?
C010 C016 H016 119.3 . . ?
C013 C016 H016 119.3 . . ?
C00T C017 H01D 109.5 . . ?
C00T C017 H01E 109.5 . . ?
C00T C017 H01F 109.5 . . ?
H01D C017 H01E 109.5 . . ?
H01D C017 H01F 109.5 . . ?
H01E C017 H01F 109.5 . . ?
Cl3 C21 Cl1 108.7(4) . . ?
Cl3 C21 D21 108.9 . . ?
Cl2 C21 Cl3 110.1(4) . . ?
Cl2 C21 Cl1 111.3(4) . . ?
Cl2 C21 D21 108.9 . . ?
Cl1 C21 D21 108.9 . . ?
C00X C019 H01G 109.5 . . ?
C00X C019 H01H 109.5 . . ?
C00X C019 H01I 109.5 . . ?
H01G C019 H01H 109.5 . . ?
H01G C019 H01I 109.5 . . ?
H01H C019 H01I 109.5 . . ?
C00G B19 C009 120.4(4) . . ?
C00J B19 C009 115.6(5) . . ?
C00J B19 C00G 123.7(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
N004 C00H C00M C00K -0.7(6) . . . . ?
N004 C00H C00M C010 179.7(5) . . . . ?
N004 C00H C00P C013 -179.7(5) . . . . ?
N004 C00Q C012 C014 179.0(5) . . . . ?
N005 C00C C00F C00D -175.0(5) . . . . ?
N005 C00C C00L C00N 178.0(5) . . . . ?
C006 C00G C00I C00E -1.7(7) . . . . ?
C006 C00G C00I C00U 178.1(5) . . . . ?
C006 C00G B19 C009 126.1(5) . . . . ?
C006 C00G B19 C00J -47.0(7) . . . . ?
C006 C00O C00X C00E -0.2(8) . . . . ?
C006 C00O C00X C019 178.6(5) . . . . ?
C007 C008 C009 C00B 1.3(7) . . . . ?
C007 C008 C009 B19 177.4(5) . . . . ?
C008 C007 C00T C00A 0.6(8) . . . . ?
C008 C007 C00T C017 -179.9(5) . . . . ?
C008 C009 C00B C00A -2.3(7) . . . . ?
C008 C009 C00B C00W 175.0(5) . . . . ?
C008 C009 B19 C00G 117.0(5) . . . . ?
C008 C009 B19 C00J -69.4(6) . . . . ?
C00B C009 B19 C00G -67.1(6) . . . . ?
C00B C009 B19 C00J 106.6(5) . . . . ?
C00B C00A C00T C007 -1.6(8) . . . . ?
C00B C00A C00T C017 178.9(5) . . . . ?
C00C C00L C00N C00J -3.1(8) . . . . ?
C00D C00J C00N C00L 4.3(7) . . . . ?
C00D C00J B19 C009 150.6(5) . . . . ?
C00D C00J B19 C00G -36.0(8) . . . . ?
C00F C00C C00L C00N -1.2(7) . . . . ?
C00F C00D C00J C00N -1.3(7) . . . . ?
C00F C00D C00J B19 171.6(5) . . . . ?
C00F C00D C20 N004 10.4(7) . . . . ?
C00G C006 C00O C00X -3.0(8) . . . . ?
C00H N004 C00Q C00K -3.0(6) . . . . ?
C00H N004 C00Q C012 178.1(5) . . . . ?
C00H N004 C20 C00D -86.7(6) . . . . ?
C00H C00M C010 C016 0.2(8) . . . . ?
C00H C00P C013 C016 -0.4(8) . . . . ?
C00I C00E C00X C00O 2.4(8) . . . . ?
C00I C00E C00X C019 -176.4(5) . . . . ?
C00I C00G B19 C009 -47.8(7) . . . . ?
C00I C00G B19 C00J 139.1(5) . . . . ?
C00J C00D C00F C00C -3.0(8) . . . . ?
C00J C00D C20 N004 -167.9(4) . . . . ?
C00K C00M C010 C016 -179.2(6) . . . . ?
C00K C00Q C012 C014 0.2(8) . . . . ?
C00K C00V C011 C014 -0.1(9) . . . . ?
C00L C00C C00F C00D 4.2(7) . . . . ?
C00M C00H C00P C013 0.5(8) . . . . ?
C00M C00K C00Q N004 2.5(6) . . . . ?
C00M C00K C00Q C012 -178.5(5) . . . . ?
C00M C00K C00V C011 177.9(6) . . . . ?
C00M C010 C016 C013 -0.2(8) . . . . ?
C00N C00J B19 C009 -36.5(6) . . . . ?
C00N C00J B19 C00G 136.9(5) . . . . ?
C00O C006 C00G C00I 3.9(7) . . . . ?
C00O C006 C00G B19 -170.4(5) . . . . ?
C00P C00H C00M C00K 179.2(5) . . . . ?
C00P C00H C00M C010 -0.4(8) . . . . ?
C00P C013 C016 C010 0.3(9) . . . . ?
C00Q N004 C00H C00M 2.3(6) . . . . ?
C00Q N004 C00H C00P -177.6(5) . . . . ?
C00Q N004 C20 C00D 82.4(6) . . . . ?
C00Q C00K C00M C00H -1.1(6) . . . . ?
C00Q C00K C00M C010 178.4(6) . . . . ?
C00Q C00K C00V C011 -0.1(8) . . . . ?
C00Q C012 C014 C011 -0.4(9) . . . . ?
C20 N004 C00H C00M 172.9(5) . . . . ?
C20 N004 C00H C00P -7.0(8) . . . . ?
C20 N004 C00Q C00K -173.6(4) . . . . ?
C20 N004 C00Q C012 7.5(9) . . . . ?
C20 C00D C00F C00C 178.8(5) . . . . ?
C20 C00D C00J C00N 177.0(5) . . . . ?
C20 C00D C00J B19 -10.1(8) . . . . ?
C00S C008 C009 C00B 178.4(5) . . . . ?
C00S C008 C009 B19 -5.5(7) . . . . ?
C00T C007 C008 C009 -0.5(8) . . . . ?
C00T C007 C008 C00S -177.7(5) . . . . ?
C00T C00A C00B C009 2.5(8) . . . . ?
C00T C00A C00B C00W -174.9(5) . . . . ?
C00V C00K C00M C00H -179.3(6) . . . . ?
C00V C00K C00M C010 0.1(11) . . . . ?
C00V C00K C00Q N004 -179.0(5) . . . . ?
C00V C00K C00Q C012 0.1(8) . . . . ?
C00V C011 C014 C012 0.4(9) . . . . ?
C00X C00E C00I C00G -1.5(8) . . . . ?
C00X C00E C00I C00U 178.8(5) . . . . ?
C00Y C006 C00G C00I -178.6(5) . . . . ?
C00Y C006 C00G B19 7.1(7) . . . . ?
C00Y C006 C00O C00X 179.3(5) . . . . ?
C00Z N005 C00C C00F -15.0(7) . . . . ?
C00Z N005 C00C C00L 165.8(5) . . . . ?
C015 N005 C00C C00F -178.6(5) . . . . ?
C015 N005 C00C C00L 2.2(8) . . . . ?
B19 C009 C00B C00A -178.4(5) . . . . ?
B19 C009 C00B C00W -1.1(7) . . . . ?
B19 C00G C00I C00E 172.4(5) . . . . ?
B19 C00G C00I C00U -7.8(8) . . . . ?
B19 C00J C00N C00L -169.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
