# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_tx15347_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2lqcc2
_database_code_depnum_ccdc_archive 'CCDC 2404774'
loop_
_audit_author_name
_audit_author_address
'YANG JI'
;RENMIN UNIVERSITY of CHINA
China
;
_audit_update_record             
;
2024-11-23 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_audit_creation_date             2024-03-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N3 O'
_chemical_formula_sum            'C16 H19 N3 O'
_chemical_formula_weight         269.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   11.61718(18)
_cell_length_b                   5.70808(9)
_cell_length_c                   21.0321(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.6542(15)
_cell_angle_gamma                90
_cell_volume                     1365.92(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7707
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      75.8970
_cell_measurement_theta_min      4.0140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8987
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.266
_diffrn_reflns_theta_min         4.041
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  65.00   0.50    0.40    --  108.85-125.00  30.00   52
  2  ω     72.00  98.00   0.50    0.40    --  108.85-125.00  30.00   52
  3  ω     58.00 105.00   0.50    0.40    --  108.85 -94.00 150.00   94
  4  ω     37.00  71.00   0.50    0.40    --  108.85 -61.00  90.00   68
  5  ω     41.00  73.00   0.50    0.40    --  108.85 -61.00  60.00   64
  6  ω      4.00  34.00   0.50    0.20    --   46.67 -28.00  47.00   60
  7  ω     85.00 111.00   0.50    0.40    --  108.85  77.00 -30.00   52
  8  ω    100.00 137.00   0.50    0.40    --  108.85  28.00-151.00   74
  9  ω     23.00 105.00   0.50    0.20    --   46.67  77.00 -60.00  164
 10  ω     57.00 123.00   0.50    0.20    --   46.67  28.00-151.00  132
 11  ω     81.00 108.00   0.50    0.20    --   46.67  57.00 -90.00   54
 12  ω     34.00  77.00   0.50    0.20    --   46.67  57.00 -90.00   86
 13  ω    -38.00  26.00   0.50    0.20    --  -46.67  38.00 -30.00  128
 14  ω    -28.00  21.00   0.50    0.20    --  -46.67  28.00-151.00   98
 15  ω    -56.00 -31.00   0.50    0.40    -- -104.50  77.00 -60.00   50
 16  ω    -61.00 -31.00   0.50    0.40    -- -104.50  61.00-120.00   60
 17  ω    -60.00 -31.00   0.50    0.40    -- -104.50  61.00 -60.00   58
 18  ω    -67.00 -31.00   0.50    0.40    -- -104.50  61.00-150.00   72
 19  ω   -100.00 -75.00   0.50    0.40    -- -104.50  77.00 -60.00   50
 20  ω    -68.00 -31.00   0.50    0.40    -- -104.50  61.00-180.00   74
 21  ω    -66.00 -31.00   0.50    0.40    -- -104.50  61.00 -30.00   70
 22  ω    -64.00 -33.00   0.50    0.40    -- -104.50  61.00   0.00   62
 23  ω    -23.00   8.00   0.50    0.20    --  -46.67  19.00 150.00   62
 24  ω   -110.00 -34.00   0.50    0.40    -- -104.50 125.00   0.00  152
 25  ω   -105.00 -80.00   0.50    0.40    -- -104.50 -78.00  16.26   50
 26  ω   -128.00 -80.00   0.50    0.40    -- -104.50 -79.00  -8.32   96
 27  ω   -111.00 -85.00   0.50    0.40    -- -104.50 -77.00   0.00   52
 28  ω   -107.00 -81.00   0.50    0.40    -- -104.50 -77.00 -30.00   52
 29  ω   -110.00 -84.00   0.50    0.40    -- -104.50 -76.00 -48.60   52
 30  ω   -108.00 -82.00   0.50    0.40    -- -104.50 -77.00 -60.00   52
 31  ω   -172.00-112.00   0.50    0.40    -- -104.50 -77.00 -60.00  120
 32  ω   -167.00-141.00   0.50    0.40    -- -104.50 -77.00 -30.00   52
 33  ω   -129.00 -85.00   0.50    0.40    -- -104.50 -67.00  -6.31   88
 34  ω   -109.00 -83.00   0.50    0.40    -- -104.50 -77.00  30.00   52
 35  ω   -160.00-135.00   0.50    0.40    -- -104.50 -67.00  -6.31   50
 36  ω   -171.00-145.00   0.50    0.40    -- -104.50 -76.00 -48.60   52
 37  ω   -173.00-147.00   0.50    0.40    -- -104.50 -61.00 -90.00   52
 38  ω   -116.00 -87.00   0.50    0.40    -- -104.50 -65.00 -91.56   58
 39  ω   -115.00 -89.00   0.50    0.40    -- -104.50 -61.00 -90.00   52
 40  ω   -113.00 -87.00   0.50    0.40    -- -104.50 -61.00 -60.00   52
 41  ω   -110.00 -85.00   0.50    0.40    -- -104.50 -65.00 -29.99   50
 42  ω   -113.00 -87.00   0.50    0.40    -- -104.50 -61.00   0.00   52
 43  ω   -121.00 -88.00   0.50    0.40    -- -104.50 -57.00  14.91   66
 44  ω   -125.00 -91.00   0.50    0.40    -- -104.50 -50.00  -6.25   68
 45  ω   -130.00 -93.00   0.50    0.40    -- -104.50 -45.00 -69.30   74
 46  ω   -124.00 -93.00   0.50    0.40    -- -104.50 -45.00 -60.00   62
 47  ω   -117.00 -91.00   0.50    0.40    -- -104.50 -44.00 -48.04   52
 48  ω   -128.00 -91.00   0.50    0.40    -- -104.50 -30.00   0.00   74
 49  ω   -123.00 -92.00   0.50    0.40    -- -104.50 -30.00 -60.00   62
 50  ω   -130.00 -94.00   0.50    0.40    -- -104.50 -45.00 -90.00   72
 51  ω   -169.00 -94.00   0.50    0.40    -- -104.50 -52.00-110.22  150
 52  ω   -171.00-137.00   0.50    0.40    -- -104.50 -30.00   0.00   68
 53  ω   -132.00 -90.00   0.50    0.40    -- -104.50 -28.00  47.00   84
 54  ω   -107.00 -68.00   0.50    0.20    --  -46.67 -28.00  47.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0905079000
_diffrn_orient_matrix_UB_12      0.0655235000
_diffrn_orient_matrix_UB_13      -0.0616091000
_diffrn_orient_matrix_UB_21      -0.1004093000
_diffrn_orient_matrix_UB_22      -0.0805245000
_diffrn_orient_matrix_UB_23      0.0328371000
_diffrn_orient_matrix_UB_31      -0.0086256000
_diffrn_orient_matrix_UB_32      0.2490713000
_diffrn_orient_matrix_UB_33      0.0267949000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.860
_reflns_number_gt                2608
_reflns_number_total             2662
_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 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_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         0.327
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(9)
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2662
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.067
_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)+(0.0541P)²+0.5646P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2)
2.b Ternary CH refined with riding coordinates:
 C8(H8)
2.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2A), C3(H3A), C4(H4), C5(H5), C11(H11), C12(H12),
 C14(H14), C15(H15)
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.13184(12) 1.0674(3) 0.64909(7) 0.0357(4) Uani 1 1 d . . . . .
N1 N 0.39696(14) 0.2179(3) 0.39777(8) 0.0274(4) Uani 1 1 d . . . . .
H1 H 0.427893 0.351795 0.413448 0.033 Uiso 1 1 calc R U . . .
N2 N 0.31685(15) -0.2260(3) 0.35180(8) 0.0277(4) Uani 1 1 d . . . . .
H2 H 0.274976 -0.338815 0.329766 0.033 Uiso 1 1 d R U . . .
N3 N 0.33743(15) 0.3971(4) 0.51307(8) 0.0305(4) Uani 1 1 d . . . . .
H3 H 0.413601 0.400750 0.514389 0.037 Uiso 1 1 calc R U . . .
C1 C 0.40737(16) 0.1466(3) 0.33555(9) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.46072(17) 0.2913(4) 0.29655(10) 0.0262(4) Uani 1 1 d . . . . .
H2A H 0.487956 0.441723 0.312146 0.031 Uiso 1 1 calc R U . . .
C3 C 0.47490(17) 0.2206(4) 0.23545(10) 0.0297(4) Uani 1 1 d . . . . .
H3A H 0.511437 0.322001 0.209670 0.036 Uiso 1 1 calc R U . . .
C4 C 0.43569(17) 0.0020(4) 0.21220(10) 0.0297(5) Uani 1 1 d . . . . .
H4 H 0.445690 -0.047942 0.170564 0.036 Uiso 1 1 calc R U . . .
C5 C 0.38148(17) -0.1443(4) 0.25024(10) 0.0272(4) Uani 1 1 d . . . . .
H5 H 0.353541 -0.293450 0.233989 0.033 Uiso 1 1 calc R U . . .
C6 C 0.36753(16) -0.0753(3) 0.31185(9) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.25368(17) -0.1021(4) 0.39501(9) 0.0283(4) Uani 1 1 d . . . . .
H7A H 0.223469 -0.216205 0.423103 0.034 Uiso 1 1 calc R U . . .
H7B H 0.185772 -0.017645 0.368979 0.034 Uiso 1 1 calc R U . . .
C8 C 0.33494(17) 0.0711(4) 0.43686(9) 0.0269(4) Uani 1 1 d . . . . .
H8 H 0.394369 -0.018782 0.468642 0.032 Uiso 1 1 calc R U . . .
C9 C 0.26386(17) 0.2219(4) 0.47437(9) 0.0296(4) Uani 1 1 d . . . . .
H9A H 0.199933 0.300790 0.443548 0.035 Uiso 1 1 calc R U . . .
H9B H 0.227534 0.121085 0.503197 0.035 Uiso 1 1 calc R U . . .
C10 C 0.28508(17) 0.5606(4) 0.54835(9) 0.0265(4) Uani 1 1 d . . . . .
C11 C 0.35631(16) 0.7185(4) 0.58946(9) 0.0279(4) Uani 1 1 d . . . . .
H11 H 0.439157 0.710846 0.593462 0.033 Uiso 1 1 calc R U . . .
C12 C 0.30917(17) 0.8858(4) 0.62449(9) 0.0284(4) Uani 1 1 d . . . . .
H12 H 0.359710 0.987835 0.653069 0.034 Uiso 1 1 calc R U . . .
C13 C 0.18763(17) 0.9049(4) 0.61788(9) 0.0280(4) Uani 1 1 d . . . . .
C14 C 0.11561(17) 0.7502(4) 0.57682(10) 0.0317(5) Uani 1 1 d . . . . .
H14 H 0.032683 0.761748 0.571827 0.038 Uiso 1 1 calc R U . . .
C15 C 0.16342(17) 0.5791(4) 0.54304(9) 0.0304(5) Uani 1 1 d . . . . .
H15 H 0.112792 0.472966 0.515923 0.036 Uiso 1 1 calc R U . . .
C16 C 0.20408(19) 1.2274(4) 0.69125(11) 0.0353(5) Uani 1 1 d . . . . .
H16A H 0.247471 1.325796 0.665986 0.053 Uiso 1 1 calc R U . . .
H16B H 0.259764 1.139968 0.723943 0.053 Uiso 1 1 calc R U . . .
H16C H 0.154770 1.326513 0.712869 0.053 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.372(3) . ?
O1 C16 1.422(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.399(2) . ?
N1 C8 1.462(3) . ?
N2 H2 0.8802 . ?
N2 C6 1.412(2) . ?
N2 C7 1.461(3) . ?
N3 H3 0.8800 . ?
N3 C9 1.453(3) . ?
N3 C10 1.405(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.405(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.519(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.519(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.399(3) . ?
C10 C15 1.399(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.395(3) . ?
C13 C14 1.391(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C13 O1 C16 117.12(15) . . ?
C1 N1 H1 119.8 . . ?
C1 N1 C8 120.33(17) . . ?
C8 N1 H1 119.8 . . ?
C6 N2 H2 112.6 . . ?
C6 N2 C7 113.42(16) . . ?
C7 N2 H2 112.8 . . ?
C9 N3 H3 120.5 . . ?
C10 N3 H3 120.5 . . ?
C10 N3 C9 118.98(16) . . ?
N1 C1 C6 120.66(17) . . ?
C2 C1 N1 120.69(17) . . ?
C2 C1 C6 118.63(17) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 C1 121.45(19) . . ?
C3 C2 H2A 119.3 . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.51(18) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.05(19) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 N2 119.03(16) . . ?
C5 C6 N2 121.44(18) . . ?
C5 C6 C1 119.51(17) . . ?
N2 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
N2 C7 C8 110.13(15) . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
N1 C8 C7 111.49(15) . . ?
N1 C8 H8 108.5 . . ?
N1 C8 C9 110.40(18) . . ?
C7 C8 H8 108.5 . . ?
C7 C8 C9 109.29(15) . . ?
C9 C8 H8 108.5 . . ?
N3 C9 C8 111.16(16) . . ?
N3 C9 H9A 109.4 . . ?
N3 C9 H9B 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 N3 119.31(17) . . ?
C11 C10 C15 117.56(18) . . ?
C15 C10 N3 123.11(18) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.69(17) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.13(19) . . ?
C13 C12 H12 119.9 . . ?
O1 C13 C12 124.84(19) . . ?
O1 C13 C14 116.32(17) . . ?
C14 C13 C12 118.84(19) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.79(18) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 120.97(19) . . ?
C14 C15 H15 119.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C13 C14 C15 -179.95(19) . . . . ?
N1 C1 C2 C3 178.08(17) . . . . ?
N1 C1 C6 N2 -0.1(2) . . . . ?
N1 C1 C6 C5 -178.49(17) . . . . ?
N1 C8 C9 N3 -54.6(2) . . . . ?
N2 C7 C8 N1 49.7(2) . . . . ?
N2 C7 C8 C9 172.02(16) . . . . ?
N3 C10 C11 C12 178.88(18) . . . . ?
N3 C10 C15 C14 -177.2(2) . . . . ?
C1 N1 C8 C7 -19.9(2) . . . . ?
C1 N1 C8 C9 -141.53(17) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C1 C6 N2 177.98(17) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 N2 -177.47(17) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C6 N2 C7 C8 -56.6(2) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C7 N2 C6 C1 32.1(2) . . . . ?
C7 N2 C6 C5 -149.51(18) . . . . ?
C7 C8 C9 N3 -177.59(17) . . . . ?
C8 N1 C1 C2 176.46(17) . . . . ?
C8 N1 C1 C6 -5.5(3) . . . . ?
C9 N3 C10 C11 175.28(17) . . . . ?
C9 N3 C10 C15 -6.8(3) . . . . ?
C10 N3 C9 C8 176.65(17) . . . . ?
C10 C11 C12 C13 -1.9(3) . . . . ?
C11 C10 C15 C14 0.8(3) . . . . ?
C11 C12 C13 O1 -178.46(19) . . . . ?
C11 C12 C13 C14 1.4(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C10 -1.3(3) . . . . ?
C15 C10 C11 C12 0.8(3) . . . . ?
C16 O1 C13 C12 -0.1(3) . . . . ?
C16 O1 C13 C14 -179.93(18) . . . . ?

_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 1.687
_oxdiff_exptl_absorpt_empirical_full_min 0.669
####################################################################### 
# 
# 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_FX1252
_database_code_depnum_ccdc_archive 'CCDC 2431788'
loop_
_audit_author_name
_audit_author_address
'YANG JI'
;RENMIN UNIVERSITY of CHINA
China
;
_audit_update_record             
;
2025-03-17 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_audit_creation_date             2025-03-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H28 B N3 O2'
_chemical_formula_sum            'C21 H28 B N3 O2'
_chemical_formula_weight         365.27
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONB
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.3685(2)
_cell_length_b                   13.5410(4)
_cell_length_c                   14.1637(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1988.58(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7936
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      75.2970
_cell_measurement_theta_min      4.5030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.114a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12470
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.970
_diffrn_reflns_theta_min         4.518
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(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 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00 102.00   0.50    0.05    --   46.62-140.00  46.00  108
  2  ω     31.00  56.00   0.50    0.05    --  103.69-137.00 134.00   50
  3  ω     81.00 118.00   0.50    0.05    --  103.69-133.00 -48.00   74
  4  ω     82.00 112.00   0.50    0.05    --  103.69-130.00-140.00   60
  5  ω     33.00  78.00   0.50    0.05    --  103.69-130.00-140.00   90
  6  ω     35.00  72.00   0.50    0.05    --  103.69 -61.00-120.00   74
  7  ω     31.00  75.00   0.50    0.05    --  103.69 -61.00-150.00   88
  8  ω     36.00  74.00   0.50    0.05    --  103.69 -61.00 -90.00   76
  9  ω     31.00  73.00   0.50    0.05    --  103.69 -61.00   0.00   84
 10  ω    -25.00 116.00   0.50    0.05    --   46.62   3.00-172.00  282
 11  ω     89.00 129.00   0.50    0.05    --  103.69 125.00-120.00   80
 12  ω    143.00 173.00   0.50    0.05    --  103.69 125.00-120.00   60
 13  ω     92.00 173.00   0.50    0.05    --  103.69 125.00 120.00  162
 14  ω   -174.00-117.00   0.50    0.05    -- -103.69   3.00-172.00  114
 15  ω    -23.00   6.00   0.50    0.05    --  -46.62  19.00-180.00   58
 16  ω    -68.00 -43.00   0.50    0.05    -- -103.69  61.00-180.00   50
 17  ω    -69.00 -43.00   0.50    0.05    -- -103.69 137.00-163.00   52
 18  ω   -119.00 -75.00   0.50    0.05    -- -103.69 137.00-163.00   88
 19  ω   -155.00 -96.00   0.50    0.05    -- -103.69 -77.00  90.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0006778000
_diffrn_orient_matrix_UB_12      -0.1101813000
_diffrn_orient_matrix_UB_13      -0.0272723000
_diffrn_orient_matrix_UB_21      -0.0058259000
_diffrn_orient_matrix_UB_22      0.0284138000
_diffrn_orient_matrix_UB_23      -0.1052501000
_diffrn_orient_matrix_UB_31      0.1484519000
_diffrn_orient_matrix_UB_32      0.0016288000
_diffrn_orient_matrix_UB_33      -0.0039862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                3706
_reflns_number_total             4002
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.114a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.114a 64-bit (release 14-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.114a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1475 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(11)
_refine_ls_extinction_coef       0.0015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4002
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.065
_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)+(0.0604P)²+0.1763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1084
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), N2(H2A), N3(H3A), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12),
  C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.5257(2) 0.04228(18) 0.34265(17) 0.0365(5) Uani 1 1 d . . . . .
O1 O 0.61114(15) 0.05407(15) 0.27034(12) 0.0555(5) Uani 1 1 d . . . . .
O2 O 0.42913(14) -0.02332(11) 0.32194(11) 0.0424(4) Uani 1 1 d . . . . .
N1 N 0.63344(17) 0.53044(14) 0.65081(15) 0.0450(5) Uani 1 1 d . . . . .
H1A H 0.7119 0.5352 0.6741 0.054 Uiso 1 1 calc R U . . .
N2 N 0.36887(19) 0.52061(16) 0.63098(16) 0.0530(5) Uani 1 1 d . . . . .
H2A H 0.2895 0.5108 0.6111 0.064 Uiso 1 1 calc R U . . .
N3 N 0.5950(2) 0.25928(14) 0.68809(13) 0.0458(5) Uani 1 1 d . . . . .
H3A H 0.5699 0.2314 0.7411 0.055 Uiso 1 1 calc R U . . .
C1 C 0.5664(2) 0.61475(17) 0.62236(15) 0.0417(5) Uani 1 1 d . . . . .
C2 C 0.6276(3) 0.70378(18) 0.60501(18) 0.0489(6) Uani 1 1 d . . . . .
H2 H 0.7185 0.7084 0.6123 0.059 Uiso 1 1 calc R U . . .
C3 C 0.5578(3) 0.7867(2) 0.57704(19) 0.0585(7) Uani 1 1 d . . . . .
H3 H 0.6011 0.8475 0.5663 0.070 Uiso 1 1 calc R U . . .
C4 C 0.4268(3) 0.7808(2) 0.56491(19) 0.0581(7) Uani 1 1 d . . . . .
H4 H 0.3797 0.8368 0.5437 0.070 Uiso 1 1 calc R U . . .
C5 C 0.3635(3) 0.6928(2) 0.58379(18) 0.0524(6) Uani 1 1 d . . . . .
H5 H 0.2726 0.6892 0.5763 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4309(2) 0.60960(18) 0.61356(16) 0.0430(5) Uani 1 1 d . . . . .
C7 C 0.4367(2) 0.44446(18) 0.68212(19) 0.0484(5) Uani 1 1 d . . . . .
H7A H 0.3902 0.3809 0.6762 0.058 Uiso 1 1 calc R U . . .
H7B H 0.4417 0.4619 0.7499 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5715(2) 0.43494(16) 0.64128(15) 0.0401(5) Uani 1 1 d . . . . .
H8 H 0.5653 0.4174 0.5729 0.048 Uiso 1 1 calc R U . . .
C9 C 0.6516(2) 0.35693(16) 0.69251(16) 0.0434(5) Uani 1 1 d . . . . .
H9A H 0.7388 0.3547 0.6642 0.052 Uiso 1 1 calc R U . . .
H9B H 0.6611 0.3764 0.7595 0.052 Uiso 1 1 calc R U . . .
C10 C 0.5784(2) 0.20797(15) 0.60511(15) 0.0365(5) Uani 1 1 d . . . . .
C11 C 0.6519(2) 0.22777(15) 0.52492(15) 0.0371(5) Uani 1 1 d . . . . .
H11 H 0.7145 0.2790 0.5261 0.045 Uiso 1 1 calc R U . . .
C12 C 0.6340(2) 0.17307(16) 0.44381(15) 0.0363(4) Uani 1 1 d . . . . .
H12 H 0.6860 0.1872 0.3903 0.044 Uiso 1 1 calc R U . . .
C13 C 0.5422(2) 0.09754(15) 0.43717(14) 0.0354(4) Uani 1 1 d . . . . .
C14 C 0.4699(2) 0.07817(16) 0.51878(15) 0.0390(5) Uani 1 1 d . . . . .
H14 H 0.4069 0.0273 0.5173 0.047 Uiso 1 1 calc R U . . .
C15 C 0.4877(2) 0.13090(16) 0.60107(15) 0.0395(5) Uani 1 1 d . . . . .
H15 H 0.4382 0.1150 0.6555 0.047 Uiso 1 1 calc R U . . .
C16 C 0.5543(2) 0.0078(2) 0.18678(18) 0.0548(7) Uani 1 1 d . . . . .
C17 C 0.4640(2) -0.06997(18) 0.23135(17) 0.0473(6) Uani 1 1 d . . . . .
C18 C 0.6624(3) -0.0319(3) 0.1261(3) 0.0861(12) Uani 1 1 d . . . . .
H18A H 0.7160 0.0229 0.1038 0.129 Uiso 1 1 calc R U . . .
H18B H 0.6260 -0.0670 0.0718 0.129 Uiso 1 1 calc R U . . .
H18C H 0.7153 -0.0775 0.1634 0.129 Uiso 1 1 calc R U . . .
C19 C 0.4811(3) 0.0871(2) 0.13305(19) 0.0680(8) Uani 1 1 d . . . . .
H19A H 0.4129 0.1142 0.1733 0.102 Uiso 1 1 calc R U . . .
H19B H 0.4426 0.0582 0.0762 0.102 Uiso 1 1 calc R U . . .
H19C H 0.5407 0.1400 0.1149 0.102 Uiso 1 1 calc R U . . .
C20 C 0.5306(4) -0.1667(2) 0.2564(3) 0.0791(10) Uani 1 1 d . . . . .
H20A H 0.6109 -0.1526 0.2903 0.119 Uiso 1 1 calc R U . . .
H20B H 0.5501 -0.2033 0.1985 0.119 Uiso 1 1 calc R U . . .
H20C H 0.4737 -0.2063 0.2966 0.119 Uiso 1 1 calc R U . . .
C21 C 0.3428(2) -0.0908(2) 0.17650(19) 0.0559(6) Uani 1 1 d . . . . .
H21A H 0.2930 -0.1422 0.2088 0.084 Uiso 1 1 calc R U . . .
H21B H 0.3655 -0.1135 0.1129 0.084 Uiso 1 1 calc R U . . .
H21C H 0.2911 -0.0305 0.1721 0.084 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.364(3) . ?
B1 O2 1.370(3) . ?
B1 C13 1.543(3) . ?
O1 C16 1.463(3) . ?
O2 C17 1.475(3) . ?
N1 C1 1.396(3) . ?
N1 C8 1.450(3) . ?
N2 C6 1.388(3) . ?
N2 C7 1.443(3) . ?
N3 C9 1.448(3) . ?
N3 C10 1.376(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.412(3) . ?
C2 C3 1.393(4) . ?
C3 C4 1.371(4) . ?
C4 C5 1.387(4) . ?
C5 C6 1.391(4) . ?
C7 C8 1.518(3) . ?
C8 C9 1.527(3) . ?
C10 C11 1.394(3) . ?
C10 C15 1.406(3) . ?
C11 C12 1.379(3) . ?
C12 C13 1.401(3) . ?
C13 C14 1.402(3) . ?
C14 C15 1.379(3) . ?
C16 C17 1.545(4) . ?
C16 C18 1.512(3) . ?
C16 C19 1.519(4) . ?
C17 C20 1.522(4) . ?
C17 C21 1.503(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 B1 O2 112.94(18) . . ?
O1 B1 C13 121.53(19) . . ?
O2 B1 C13 125.5(2) . . ?
B1 O1 C16 107.20(16) . . ?
B1 O2 C17 106.55(17) . . ?
C1 N1 C8 118.79(18) . . ?
C6 N2 C7 118.93(19) . . ?
C10 N3 C9 123.26(18) . . ?
N1 C1 C6 118.7(2) . . ?
C2 C1 N1 122.3(2) . . ?
C2 C1 C6 118.9(2) . . ?
C1 C2 C3 120.9(2) . . ?
C4 C3 C2 120.3(3) . . ?
C3 C4 C5 119.6(3) . . ?
C4 C5 C6 121.1(2) . . ?
N2 C6 C1 119.2(2) . . ?
N2 C6 C5 121.6(2) . . ?
C5 C6 C1 119.1(2) . . ?
N2 C7 C8 108.5(2) . . ?
N1 C8 C7 107.26(18) . . ?
N1 C8 C9 109.37(17) . . ?
C7 C8 C9 112.24(19) . . ?
N3 C9 C8 112.98(18) . . ?
N3 C10 C11 122.07(19) . . ?
N3 C10 C15 119.51(19) . . ?
C11 C10 C15 118.39(19) . . ?
C12 C11 C10 120.11(19) . . ?
C11 C12 C13 122.67(19) . . ?
C12 C13 B1 119.18(19) . . ?
C12 C13 C14 116.39(18) . . ?
C14 C13 B1 124.43(19) . . ?
C15 C14 C13 121.90(19) . . ?
C14 C15 C10 120.52(19) . . ?
O1 C16 C17 101.87(19) . . ?
O1 C16 C18 108.3(2) . . ?
O1 C16 C19 107.7(2) . . ?
C18 C16 C17 116.0(3) . . ?
C18 C16 C19 109.7(3) . . ?
C19 C16 C17 112.6(2) . . ?
O2 C17 C16 102.23(17) . . ?
O2 C17 C20 106.0(2) . . ?
O2 C17 C21 109.00(18) . . ?
C20 C17 C16 114.0(2) . . ?
C21 C17 C16 115.1(2) . . ?
C21 C17 C20 109.7(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.388
_oxdiff_exptl_absorpt_empirical_full_min 0.685
