# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_8_186
_database_code_depnum_ccdc_archive 'CCDC 2452797'
loop_
_audit_author_name
_audit_author_address
'hydroxy ketone'
;USTC
China
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2025-09-17 downloaded from the CCDC.
;
_audit_creation_date             2024-11-09
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 O2'
_chemical_formula_sum            'C21 H16 O2'
_chemical_formula_weight         300.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.13513(12)
_cell_length_b                   6.32967(9)
_cell_length_c                   12.14214(15)
_cell_angle_alpha                90
_cell_angle_beta                 105.7256(13)
_cell_angle_gamma                90
_cell_volume                     749.788(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7666
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.6090
_cell_measurement_theta_min      5.0360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9116
_diffrn_reflns_point_group_measured_fraction_full 0.842
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.719
_diffrn_reflns_theta_min         5.057
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     55.00  88.00   0.50    0.05    --   62.21  15.00 120.00   66
  2  ω     74.00 115.00   0.50    0.05    --   75.66  18.00 104.59   82
  3  ω     85.00 110.00   0.50    0.05    --   68.27  24.00  65.95   50
  4  ω     61.00 102.00   0.50    0.05    --   62.21  15.00  60.00   82
  5  ω     55.00  99.00   0.50    0.05    --   62.21  15.00 -60.00   88
  6  ω     61.00 102.00   0.50    0.05    --   62.21  15.00  17.00   82
  7  ω     62.00 101.00   0.50    0.05    --   62.21  15.00 -30.00   78
  8  ω     69.00 109.00   0.50    0.05    --   71.27  15.00  17.00   80
  9  ω     64.00 105.00   0.50    0.05    --   71.27  15.00-120.00   82
 10  ω     68.00  98.00   0.50    0.05    --   68.27  18.00-155.38   60
 11  ω     89.00 115.00   0.50    0.05    --   75.66  20.00-169.93   52
 12  ω     57.00 103.00   0.50    0.05    --   62.21  15.00-180.00   92
 13  ω     75.00 108.00   0.50    0.05    --   74.33  15.00 -90.00   66
 14  ω     71.00 108.00   0.50    0.05    --   74.33  15.00 -30.00   74
 15  ω     67.00  92.00   0.50    0.05    --   74.33  15.00  17.00   50
 16  ω     60.00  86.00   0.50    0.05    --   62.21  15.00 150.00   52
 17  ω     76.00 102.00   0.50    0.05    --   74.33  15.00 150.00   52
 18  ω     67.00 110.00   0.50    0.05    --   71.27  15.00 120.00   86
 19  ω     68.00 104.00   0.50    0.05    --   74.33  15.00  60.00   72
 20  ω     16.00  41.00   0.50    0.05    --    2.00  22.00-172.16   50
 21  ω     43.00  68.00   0.50    0.05    --   30.00  21.00-165.93   50
 22  ω     32.00  58.00   0.50    0.05    --   18.00  22.00-120.97   52
 23  ω     57.00  86.00   0.50    0.05    --   46.00  19.00-170.94   58
 24  ω     52.00  77.00   0.50    0.05    --   38.00  22.00  28.56   50
 25  ω     36.00  64.00   0.50    0.05    --   22.00  21.00 154.97   56
 26  ω     21.00  46.00   0.50    0.05    --    6.00  22.00 175.85   50
 27  ω     21.00  47.00   0.50    0.05    --   22.00-139.00 -48.27   52
 28  ω     25.00  50.00   0.50    0.05    --   62.21-125.00-120.00   50
 29  ω     25.00  78.00   0.50    0.05    --   62.21-125.00-150.00  106
 30  ω     27.00  58.00   0.50    0.05    --   62.21-125.00-180.00   62
 31  ω     26.00  52.00   0.50    0.05    --   62.21-125.00 -30.00   52
 32  ω     29.00  60.00   0.50    0.05    --   62.21-125.00 -90.00   62
 33  ω     25.00  50.00   0.50    0.05    --   62.21-125.00  60.00   50
 34  ω     39.00  68.00   0.50    0.05    --   71.27-125.00  90.00   58
 35  ω     45.00  77.00   0.50    0.05    --   62.21-125.00 120.00   64
 36  ω     64.00  90.00   0.50    0.05    --   74.33-125.00 120.00   52
 37  ω     42.00  77.00   0.50    0.05    --   62.21-125.00 150.00   70
 38  ω     54.00  83.00   0.50    0.05    --   71.27-125.00 120.00   58
 39  ω     42.00  77.00   0.50    0.05    --   74.33-125.00  30.00   70
 40  ω     55.00  90.00   0.50    0.05    --   74.33-125.00 150.00   70
 41  ω     48.00  75.00   0.50    0.05    --   74.33-125.00 -30.00   54
 42  ω     40.00  66.00   0.50    0.05    --   74.33-125.00   0.00   52
 43  ω     38.00  73.00   0.50    0.05    --   74.33-125.00 -90.00   70
 44  ω     41.00  71.00   0.50    0.05    --   74.33-125.00 -60.00   60
 45  ω     39.00  85.00   0.50    0.05    --   71.27-125.00-120.00   92
 46  ω     48.00  90.00   0.50    0.05    --   74.33-125.00-150.00   84
 47  ω     56.00  89.00   0.50    0.05    --   74.33-125.00-180.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0686459000
_diffrn_orient_matrix_UB_12      0.0178225000
_diffrn_orient_matrix_UB_13      -0.0983547000
_diffrn_orient_matrix_UB_21      0.1406457000
_diffrn_orient_matrix_UB_22      -0.0439103000
_diffrn_orient_matrix_UB_23      0.0847205000
_diffrn_orient_matrix_UB_31      -0.0207958000
_diffrn_orient_matrix_UB_32      -0.2387705000
_diffrn_orient_matrix_UB_33      -0.0228962000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.546
_reflns_Friedel_fraction_full    0.676
_reflns_Friedel_fraction_max     0.638
_reflns_number_gt                2402
_reflns_number_total             2420
_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 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 846 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2420
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.050
_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)+(0.0638P)²+0.0920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0865
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56692(11) 0.5526(2) 0.55608(9) 0.0248(3) Uani 1 1 d . . . . .
O2 O 0.50920(13) 0.1732(2) 0.67592(10) 0.0258(3) Uani 1 1 d . . . . .
H2 H 0.471013 0.143105 0.607298 0.039 Uiso 1 1 calc R U . . .
C1 C 0.24485(16) 0.4681(3) 0.50352(15) 0.0232(4) Uani 1 1 d . . . . .
C2 C 0.18805(17) 0.4312(4) 0.38820(15) 0.0290(4) Uani 1 1 d . . . . .
H2A H 0.200068 0.528610 0.332200 0.035 Uiso 1 1 calc R U . . .
C3 C 0.11233(18) 0.2457(4) 0.35662(16) 0.0328(5) Uani 1 1 d . . . . .
H3 H 0.071566 0.216780 0.277963 0.039 Uiso 1 1 calc R U . . .
C4 C 0.09612(18) 0.1040(4) 0.43862(17) 0.0324(5) Uani 1 1 d . . . . .
H4 H 0.042395 -0.019392 0.415459 0.039 Uiso 1 1 calc R U . . .
C5 C 0.15723(17) 0.1388(3) 0.55478(16) 0.0272(4) Uani 1 1 d . . . . .
H5 H 0.147463 0.039188 0.610560 0.033 Uiso 1 1 calc R U . . .
C6 C 0.23214(16) 0.3213(3) 0.58662(15) 0.0232(4) Uani 1 1 d . . . . .
C7 C 0.31835(16) 0.4037(3) 0.70092(14) 0.0235(4) Uani 1 1 d . . . . .
H7 H 0.295206 0.346358 0.770126 0.028 Uiso 1 1 calc R U . . .
C8 C 0.29772(17) 0.6443(3) 0.68110(15) 0.0264(4) Uani 1 1 d . . . . .
H8A H 0.361752 0.729117 0.740824 0.032 Uiso 1 1 calc R U . . .
H8B H 0.202066 0.689303 0.673295 0.032 Uiso 1 1 calc R U . . .
C9 C 0.33524(16) 0.6462(3) 0.56574(14) 0.0239(4) Uani 1 1 d . . . . .
H9 H 0.329742 0.784678 0.525053 0.029 Uiso 1 1 calc R U . . .
C10 C 0.47395(16) 0.5371(3) 0.60059(13) 0.0207(4) Uani 1 1 d . . . . .
C11 C 0.47174(16) 0.3806(3) 0.69940(13) 0.0215(4) Uani 1 1 d . . . . .
C12 C 0.57032(17) 0.4453(3) 0.81237(14) 0.0238(4) Uani 1 1 d . . . . .
C13 C 0.64444(17) 0.6277(3) 0.82749(14) 0.0248(4) Uani 1 1 d . . . . .
H13 H 0.631766 0.724750 0.765809 0.030 Uiso 1 1 calc R U . . .
C14 C 0.74077(17) 0.6760(3) 0.93414(14) 0.0259(4) Uani 1 1 d . . . . .
C15 C 0.82176(19) 0.8612(4) 0.95020(16) 0.0317(5) Uani 1 1 d . . . . .
H15 H 0.808930 0.961145 0.889869 0.038 Uiso 1 1 calc R U . . .
C16 C 0.91875(19) 0.8985(4) 1.05183(16) 0.0364(5) Uani 1 1 d . . . . .
H16 H 0.972735 1.023324 1.061467 0.044 Uiso 1 1 calc R U . . .
C17 C 0.9379(2) 0.7509(4) 1.14180(15) 0.0367(5) Uani 1 1 d . . . . .
H17 H 1.005479 0.776466 1.211818 0.044 Uiso 1 1 calc R U . . .
C18 C 0.8605(2) 0.5719(4) 1.12938(15) 0.0343(5) Uani 1 1 d . . . . .
H18 H 0.874686 0.474717 1.191096 0.041 Uiso 1 1 calc R U . . .
C19 C 0.75878(19) 0.5282(4) 1.02564(14) 0.0284(4) Uani 1 1 d . . . . .
C20 C 0.6772(2) 0.3446(4) 1.00851(15) 0.0329(5) Uani 1 1 d . . . . .
H20 H 0.686300 0.247791 1.069920 0.039 Uiso 1 1 calc R U . . .
C21 C 0.5854(2) 0.3023(4) 0.90563(16) 0.0301(4) Uani 1 1 d . . . . .
H21 H 0.531456 0.177444 0.896269 0.036 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 C10 1.211(2) . ?
O2 H2 0.8400 . ?
O2 C11 1.417(2) . ?
C1 C2 1.382(2) . ?
C1 C6 1.403(3) . ?
C1 C9 1.518(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.398(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.379(3) . ?
C6 C7 1.518(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.547(3) . ?
C7 C11 1.566(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.548(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.520(2) . ?
C10 C11 1.560(2) . ?
C11 C12 1.518(2) . ?
C12 C13 1.362(3) . ?
C12 C21 1.425(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.428(2) . ?
C14 C15 1.414(3) . ?
C14 C19 1.426(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.374(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.410(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.363(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.422(2) . ?
C19 C20 1.409(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.367(3) . ?
C21 H21 0.9500 . ?

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
C11 O2 H2 109.5 . . ?
C2 C1 C6 121.48(18) . . ?
C2 C1 C9 131.24(17) . . ?
C6 C1 C9 107.13(15) . . ?
C1 C2 H2A 121.1 . . ?
C1 C2 C3 117.85(18) . . ?
C3 C2 H2A 121.1 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.72(17) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.23(19) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.38(18) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C7 106.72(16) . . ?
C5 C6 C1 120.28(16) . . ?
C5 C6 C7 132.91(17) . . ?
C6 C7 H7 115.8 . . ?
C6 C7 C8 100.13(15) . . ?
C6 C7 C11 106.52(13) . . ?
C8 C7 H7 115.8 . . ?
C8 C7 C11 100.53(14) . . ?
C11 C7 H7 115.8 . . ?
C7 C8 H8A 112.7 . . ?
C7 C8 H8B 112.7 . . ?
C7 C8 C9 95.31(14) . . ?
H8A C8 H8B 110.2 . . ?
C9 C8 H8A 112.7 . . ?
C9 C8 H8B 112.7 . . ?
C1 C9 C8 100.44(14) . . ?
C1 C9 H9 117.4 . . ?
C1 C9 C10 100.88(15) . . ?
C8 C9 H9 117.4 . . ?
C10 C9 C8 100.37(13) . . ?
C10 C9 H9 117.4 . . ?
O1 C10 C9 127.73(16) . . ?
O1 C10 C11 124.73(16) . . ?
C9 C10 C11 107.31(13) . . ?
O2 C11 C7 114.19(15) . . ?
O2 C11 C10 111.88(13) . . ?
O2 C11 C12 106.57(14) . . ?
C10 C11 C7 99.84(13) . . ?
C12 C11 C7 112.11(13) . . ?
C12 C11 C10 112.36(15) . . ?
C13 C12 C11 123.66(16) . . ?
C13 C12 C21 119.66(16) . . ?
C21 C12 C11 116.68(18) . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.34(17) . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 122.09(17) . . ?
C15 C14 C19 119.30(16) . . ?
C19 C14 C13 118.57(18) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.71(17) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.14(19) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C14 118.2(2) . . ?
C20 C19 C14 118.70(16) . . ?
C20 C19 C18 123.14(18) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.56(19) . . ?
C21 C20 H20 119.2 . . ?
C12 C21 H21 120.0 . . ?
C20 C21 C12 120.1(2) . . ?
C20 C21 H21 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C11 O2 -48.0(2) . . . . ?
O1 C10 C11 C7 -169.16(16) . . . . ?
O1 C10 C11 C12 71.9(2) . . . . ?
O2 C11 C12 C13 127.54(18) . . . . ?
O2 C11 C12 C21 -51.47(19) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C6 C7 C8 34.23(16) . . . . ?
C1 C6 C7 C11 -70.05(18) . . . . ?
C1 C9 C10 O1 101.9(2) . . . . ?
C1 C9 C10 C11 -72.80(16) . . . . ?
C2 C1 C6 C5 -2.6(3) . . . . ?
C2 C1 C6 C7 174.35(16) . . . . ?
C2 C1 C9 C8 153.04(19) . . . . ?
C2 C1 C9 C10 -104.1(2) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -175.45(17) . . . . ?
C5 C6 C7 C8 -149.38(19) . . . . ?
C5 C6 C7 C11 106.3(2) . . . . ?
C6 C1 C2 C3 2.5(3) . . . . ?
C6 C1 C9 C8 -31.38(17) . . . . ?
C6 C1 C9 C10 71.44(15) . . . . ?
C6 C7 C8 C9 -50.82(14) . . . . ?
C6 C7 C11 O2 -55.17(19) . . . . ?
C6 C7 C11 C10 64.34(18) . . . . ?
C6 C7 C11 C12 -176.49(17) . . . . ?
C7 C8 C9 C1 49.78(15) . . . . ?
C7 C8 C9 C10 -53.45(15) . . . . ?
C7 C11 C12 C13 -106.85(19) . . . . ?
C7 C11 C12 C21 74.1(2) . . . . ?
C8 C7 C11 O2 -159.15(13) . . . . ?
C8 C7 C11 C10 -39.64(15) . . . . ?
C8 C7 C11 C12 79.52(18) . . . . ?
C8 C9 C10 O1 -155.22(18) . . . . ?
C8 C9 C10 C11 30.07(17) . . . . ?
C9 C1 C2 C3 177.56(17) . . . . ?
C9 C1 C6 C5 -178.70(15) . . . . ?
C9 C1 C6 C7 -1.76(18) . . . . ?
C9 C10 C11 O2 126.93(15) . . . . ?
C9 C10 C11 C7 5.75(17) . . . . ?
C9 C10 C11 C12 -113.23(15) . . . . ?
C10 C11 C12 C13 4.7(2) . . . . ?
C10 C11 C12 C21 -174.35(15) . . . . ?
C11 C7 C8 C9 58.27(14) . . . . ?
C11 C12 C13 C14 -176.88(15) . . . . ?
C11 C12 C21 C20 176.78(17) . . . . ?
C12 C13 C14 C15 177.90(17) . . . . ?
C12 C13 C14 C19 0.2(3) . . . . ?
C13 C12 C21 C20 -2.3(3) . . . . ?
C13 C14 C15 C16 -176.59(18) . . . . ?
C13 C14 C19 C18 176.48(16) . . . . ?
C13 C14 C19 C20 -2.3(2) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C14 C19 C20 C21 2.2(3) . . . . ?
C15 C14 C19 C18 -1.3(2) . . . . ?
C15 C14 C19 C20 179.90(17) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C14 0.6(3) . . . . ?
C17 C18 C19 C20 179.40(19) . . . . ?
C18 C19 C20 C21 -176.54(18) . . . . ?
C19 C14 C15 C16 1.1(3) . . . . ?
C19 C20 C21 C12 0.1(3) . . . . ?
C21 C12 C13 C14 2.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.310
_oxdiff_exptl_absorpt_empirical_full_min 0.706
####################################################################### 
# 
# 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_zsm_9_120
_database_code_depnum_ccdc_archive 'CCDC 2452798'
loop_
_audit_author_name
_audit_author_address
'azide ketone'
;USTC
China
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2025-09-17 downloaded from the CCDC.
;
_audit_creation_date             2025-05-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N3 O'
_chemical_formula_sum            'C21 H15 N3 O'
_chemical_formula_weight         325.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.1974(4)
_cell_length_b                   13.1816(5)
_cell_length_c                   15.5004(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1674.90(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5487
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.1110
_cell_measurement_theta_min      4.3620
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9558
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.871
_diffrn_reflns_theta_min         4.403
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  65.00   0.50    0.08    --   42.49 -78.00 104.00  126
  2  ω     49.00  76.00   0.50    0.10    --  107.57 -78.00 104.00   54
  3  ω     40.00  75.00   0.50    0.10    --  107.57 -77.00 120.00   70
  4  ω    -18.00  60.00   0.50    0.08    --   42.49 -77.00 -90.00  156
  5  ω     37.00  74.00   0.50    0.10    --  107.57 -77.00 -30.00   74
  6  ω     96.00 139.00   0.50    0.10    --  107.57  15.00-150.00   86
  7  ω    112.00 138.00   0.50    0.10    --  107.57  78.00-131.00   52
  8  ω    143.00 175.00   0.50    0.10    --  107.57  78.00-131.00   64
  9  ω    137.00 164.00   0.50    0.10    --  107.57 126.00 -60.00   54
 10  ω     94.00 121.00   0.50    0.10    --  107.57 126.00 -60.00   54
 11  ω     99.00 175.00   0.50    0.10    --  107.57 126.00 150.00  152
 12  ω     59.00  86.00   0.50    0.10    --  107.57 -95.00 150.00   54
 13  ω    -58.00 -32.00   0.50    0.08    --  -42.49  78.00-131.00   52
 14  ω     -5.00  21.00   0.50    0.08    --  -42.49  78.00-131.00   52
 15  ω    -15.00  32.00   0.50    0.08    --  -42.49  38.00 -60.00   94
 16  ω    -13.00  35.00   0.50    0.08    --  -42.49  38.00 -30.00   96
 17  ω     -3.00  34.00   0.50    0.08    --  -42.49  38.00   0.00   74
 18  ω    -73.00 -46.00   0.50    0.10    -- -103.00  78.00-131.00   54
 19  ω    -68.00 -40.00   0.50    0.10    -- -103.00  77.00-150.00   56
 20  ω    -57.00 -29.00   0.50    0.10    -- -103.00  77.00-180.00   56
 21  ω   -121.00 -95.00   0.50    0.10    -- -103.00 -15.00-180.00   52
 22  ω   -125.00 -99.00   0.50    0.10    -- -103.00 -77.00-180.00   52
 23  ω   -160.00-132.00   0.50    0.10    -- -103.00 -77.00-180.00   56
 24  ω   -131.00 -89.00   0.50    0.10    -- -103.00 -15.00 -30.00   84
 25  ω   -174.00-106.00   0.50    0.10    -- -103.00 -78.00 104.00  136
 26  ω   -174.00-100.00   0.50    0.10    -- -103.00 -77.00 150.00  148
 27  ω   -130.00-101.00   0.50    0.10    -- -103.00 -95.00 -60.00   58
 28  ω   -174.00-147.00   0.50    0.10    -- -103.00 -95.00 -60.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1542048000
_diffrn_orient_matrix_UB_12      0.0210936000
_diffrn_orient_matrix_UB_13      0.0539789000
_diffrn_orient_matrix_UB_21      -0.0378524000
_diffrn_orient_matrix_UB_22      -0.0932128000
_diffrn_orient_matrix_UB_23      0.0565141000
_diffrn_orient_matrix_UB_31      0.1005900000
_diffrn_orient_matrix_UB_32      -0.0672910000
_diffrn_orient_matrix_UB_33      -0.0613636000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.873
_reflns_number_gt                2928
_reflns_number_total             3178
_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 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1099 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0686
_refine_ls_restrained_S_all      1.052
_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)+(0.1302P)²+0.6030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1942
_refine_ls_wR_factor_ref         0.1998
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3395(4) 0.5326(2) 0.2415(2) 0.0632(9) Uani 1 1 d . . . . .
N1 N 0.6334(5) 0.6603(3) 0.2000(2) 0.0537(8) Uani 1 1 d . . . . .
N2 N 0.6120(5) 0.5983(3) 0.1400(2) 0.0573(9) Uani 1 1 d . . . . .
N3 N 0.6004(6) 0.5503(4) 0.0801(3) 0.0762(12) Uani 1 1 d . . . . .
C1 C 0.3697(6) 0.6507(3) 0.4273(3) 0.0553(10) Uani 1 1 d . . . . .
C2 C 0.2795(8) 0.6042(3) 0.4928(3) 0.0711(14) Uani 1 1 d . . . . .
H2 H 0.166820 0.589057 0.486388 0.085 Uiso 1 1 calc R U . . .
C3 C 0.3666(10) 0.5808(3) 0.5693(3) 0.080(2) Uani 1 1 d . . . . .
H3 H 0.309583 0.552464 0.616888 0.097 Uiso 1 1 calc R U . . .
C4 C 0.5281(10) 0.5978(4) 0.5762(3) 0.0770(16) Uani 1 1 d . . . . .
H4 H 0.582316 0.580110 0.628242 0.092 Uiso 1 1 calc R U . . .
C5 C 0.6165(8) 0.6401(3) 0.5099(3) 0.0646(13) Uani 1 1 d . . . . .
H5 H 0.730725 0.650628 0.514957 0.077 Uiso 1 1 calc R U . . .
C6 C 0.5335(6) 0.6667(3) 0.4356(3) 0.0509(10) Uani 1 1 d . . . . .
C7 C 0.5953(6) 0.7093(3) 0.3508(2) 0.0502(9) Uani 1 1 d . . . . .
H7 H 0.700793 0.747306 0.353130 0.060 Uiso 1 1 calc R U . . .
C8 C 0.3228(6) 0.6835(3) 0.3363(3) 0.0578(11) Uani 1 1 d . . . . .
H8 H 0.204821 0.698016 0.325310 0.069 Uiso 1 1 calc R U . . .
C9 C 0.4429(6) 0.7713(3) 0.3235(3) 0.0555(10) Uani 1 1 d . . . . .
H9A H 0.420915 0.829264 0.362365 0.067 Uiso 1 1 calc R U . . .
H9B H 0.448260 0.794688 0.262840 0.067 Uiso 1 1 calc R U . . .
C10 C 0.5879(5) 0.6190(3) 0.2870(2) 0.0474(9) Uani 1 1 d . . . . .
C11 C 0.4017(6) 0.6010(3) 0.2822(3) 0.0527(10) Uani 1 1 d . . . . .
C12 C 0.6988(5) 0.5297(3) 0.3105(2) 0.0496(9) Uani 1 1 d . . . . .
C13 C 0.8686(6) 0.5363(4) 0.2921(3) 0.0568(10) Uani 1 1 d . . . . .
H13 H 0.910644 0.595706 0.265461 0.068 Uiso 1 1 calc R U . . .
C14 C 0.9710(6) 0.4593(4) 0.3118(3) 0.0642(12) Uani 1 1 d . . . . .
H14 H 1.084035 0.465119 0.299347 0.077 Uiso 1 1 calc R U . . .
C15 C 0.9108(6) 0.3710(4) 0.3506(3) 0.0591(11) Uani 1 1 d . . . . .
C16 C 0.6407(5) 0.4465(3) 0.3512(3) 0.0483(9) Uani 1 1 d . . . . .
H16 H 0.528275 0.443706 0.365773 0.058 Uiso 1 1 calc R U . . .
C17 C 0.7447(5) 0.3617(3) 0.3732(2) 0.0490(9) Uani 1 1 d . . . . .
C18 C 0.6849(6) 0.2751(3) 0.4124(3) 0.0607(11) Uani 1 1 d . . . . .
H18 H 0.573350 0.271094 0.428647 0.073 Uiso 1 1 calc R U . . .
C19 C 0.7868(7) 0.1957(4) 0.4276(4) 0.0720(13) Uani 1 1 d . . . . .
H19 H 0.745961 0.136147 0.454441 0.086 Uiso 1 1 calc R U . . .
C20 C 0.9536(7) 0.2010(4) 0.4037(4) 0.0741(15) Uani 1 1 d . . . . .
H20 H 1.022663 0.144419 0.413932 0.089 Uiso 1 1 calc R U . . .
C21 C 1.0148(7) 0.2842(4) 0.3670(3) 0.0695(13) Uani 1 1 d . . . . .
H21 H 1.126908 0.286531 0.351459 0.083 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 C11 1.213(5) . ?
N1 N2 1.252(5) . ?
N1 C10 1.501(5) . ?
N2 N3 1.126(5) . ?
C1 C2 1.397(6) . ?
C1 C6 1.365(7) . ?
C1 C8 1.526(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.418(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.347(10) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(6) . ?
C6 C7 1.517(6) . ?
C7 H7 1.0000 . ?
C7 C9 1.552(6) . ?
C7 C10 1.549(5) . ?
C8 H8 1.0000 . ?
C8 C9 1.532(6) . ?
C8 C11 1.518(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.546(6) . ?
C10 C12 1.531(6) . ?
C12 C13 1.424(6) . ?
C12 C16 1.351(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.352(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.400(7) . ?
C15 C17 1.411(6) . ?
C15 C21 1.450(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.447(6) . ?
C17 C18 1.383(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.359(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.418(9) . ?
C20 H20 0.9500 . ?
C20 C21 1.333(9) . ?
C21 H21 0.9500 . ?

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
N2 N1 C10 113.3(3) . . ?
N3 N2 N1 172.3(5) . . ?
C2 C1 C8 131.5(5) . . ?
C6 C1 C2 121.4(5) . . ?
C6 C1 C8 106.9(4) . . ?
C1 C2 H2 122.1 . . ?
C1 C2 C3 115.8(5) . . ?
C3 C2 H2 122.1 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.7(5) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.7(6) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.8(6) . . ?
C6 C5 H5 121.1 . . ?
C1 C6 C5 121.5(4) . . ?
C1 C6 C7 107.7(4) . . ?
C5 C6 C7 130.6(5) . . ?
C6 C7 H7 116.3 . . ?
C6 C7 C9 99.3(4) . . ?
C6 C7 C10 104.8(3) . . ?
C9 C7 H7 116.3 . . ?
C10 C7 H7 116.3 . . ?
C10 C7 C9 101.5(3) . . ?
C1 C8 H8 117.1 . . ?
C1 C8 C9 99.9(4) . . ?
C9 C8 H8 117.1 . . ?
C11 C8 C1 101.5(3) . . ?
C11 C8 H8 117.1 . . ?
C11 C8 C9 101.3(4) . . ?
C7 C9 H9A 112.8 . . ?
C7 C9 H9B 112.8 . . ?
C8 C9 C7 94.9(3) . . ?
C8 C9 H9A 112.8 . . ?
C8 C9 H9B 112.8 . . ?
H9A C9 H9B 110.2 . . ?
N1 C10 C7 106.5(3) . . ?
N1 C10 C11 105.0(3) . . ?
N1 C10 C12 110.2(3) . . ?
C11 C10 C7 100.7(3) . . ?
C12 C10 C7 114.6(3) . . ?
C12 C10 C11 118.7(3) . . ?
O1 C11 C8 129.8(4) . . ?
O1 C11 C10 123.6(4) . . ?
C8 C11 C10 106.6(3) . . ?
C13 C12 C10 119.1(4) . . ?
C16 C12 C10 121.7(4) . . ?
C16 C12 C13 119.2(4) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(4) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C17 121.3(5) . . ?
C14 C15 C21 121.6(5) . . ?
C17 C15 C21 117.1(5) . . ?
C12 C16 H16 119.0 . . ?
C12 C16 C17 122.0(4) . . ?
C17 C16 H16 119.0 . . ?
C15 C17 C16 116.3(4) . . ?
C18 C17 C15 121.5(4) . . ?
C18 C17 C16 122.2(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.6(5) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(5) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(5) . . ?
C21 C20 H20 119.5 . . ?
C15 C21 H21 119.9 . . ?
C20 C21 C15 120.1(5) . . ?
C20 C21 H21 119.9 . . ?

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 C10 C11 O1 72.9(5) . . . . ?
N1 C10 C11 C8 -106.8(3) . . . . ?
N1 C10 C12 C13 41.6(5) . . . . ?
N1 C10 C12 C16 -140.9(4) . . . . ?
N2 N1 C10 C7 -171.2(4) . . . . ?
N2 N1 C10 C11 -64.9(5) . . . . ?
N2 N1 C10 C12 63.9(5) . . . . ?
C1 C2 C3 C4 -3.4(7) . . . . ?
C1 C6 C7 C9 33.3(4) . . . . ?
C1 C6 C7 C10 -71.4(4) . . . . ?
C1 C8 C9 C7 50.9(4) . . . . ?
C1 C8 C11 O1 109.4(5) . . . . ?
C1 C8 C11 C10 -71.0(4) . . . . ?
C2 C1 C6 C5 -1.8(6) . . . . ?
C2 C1 C6 C7 174.9(4) . . . . ?
C2 C1 C8 C9 152.1(4) . . . . ?
C2 C1 C8 C11 -104.1(5) . . . . ?
C2 C3 C4 C5 1.0(7) . . . . ?
C3 C4 C5 C6 1.2(7) . . . . ?
C4 C5 C6 C1 -0.8(6) . . . . ?
C4 C5 C6 C7 -176.6(4) . . . . ?
C5 C6 C7 C9 -150.4(4) . . . . ?
C5 C6 C7 C10 105.0(5) . . . . ?
C6 C1 C2 C3 3.8(6) . . . . ?
C6 C1 C8 C9 -33.4(4) . . . . ?
C6 C1 C8 C11 70.3(4) . . . . ?
C6 C7 C9 C8 -50.9(3) . . . . ?
C6 C7 C10 N1 174.8(4) . . . . ?
C6 C7 C10 C11 65.6(4) . . . . ?
C6 C7 C10 C12 -63.0(4) . . . . ?
C7 C10 C11 O1 -176.6(4) . . . . ?
C7 C10 C11 C8 3.7(4) . . . . ?
C7 C10 C12 C13 -78.5(4) . . . . ?
C7 C10 C12 C16 99.0(4) . . . . ?
C8 C1 C2 C3 177.5(4) . . . . ?
C8 C1 C6 C5 -176.9(4) . . . . ?
C8 C1 C6 C7 -0.2(4) . . . . ?
C9 C7 C10 N1 71.8(4) . . . . ?
C9 C7 C10 C11 -37.4(4) . . . . ?
C9 C7 C10 C12 -166.0(3) . . . . ?
C9 C8 C11 O1 -148.0(5) . . . . ?
C9 C8 C11 C10 31.7(4) . . . . ?
C10 C7 C9 C8 56.4(3) . . . . ?
C10 C12 C13 C14 179.9(4) . . . . ?
C10 C12 C16 C17 179.7(3) . . . . ?
C11 C8 C9 C7 -53.1(4) . . . . ?
C11 C10 C12 C13 162.6(4) . . . . ?
C11 C10 C12 C16 -19.9(5) . . . . ?
C12 C10 C11 O1 -50.7(5) . . . . ?
C12 C10 C11 C8 129.6(4) . . . . ?
C12 C13 C14 C15 0.3(7) . . . . ?
C12 C16 C17 C15 0.7(6) . . . . ?
C12 C16 C17 C18 -177.9(4) . . . . ?
C13 C12 C16 C17 -2.9(6) . . . . ?
C13 C14 C15 C17 -2.6(7) . . . . ?
C13 C14 C15 C21 175.4(4) . . . . ?
C14 C15 C17 C16 2.1(6) . . . . ?
C14 C15 C17 C18 -179.3(4) . . . . ?
C14 C15 C21 C20 -179.7(5) . . . . ?
C15 C17 C18 C19 -1.9(7) . . . . ?
C16 C12 C13 C14 2.4(6) . . . . ?
C16 C17 C18 C19 176.7(4) . . . . ?
C17 C15 C21 C20 -1.6(7) . . . . ?
C17 C18 C19 C20 0.1(7) . . . . ?
C18 C19 C20 C21 1.0(8) . . . . ?
C19 C20 C21 C15 -0.2(8) . . . . ?
C21 C15 C17 C16 -176.0(4) . . . . ?
C21 C15 C17 C18 2.6(6) . . . . ?

_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 1.523
_oxdiff_exptl_absorpt_empirical_full_min 0.603
