# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lianghui_0706_auto
_database_code_depnum_ccdc_archive 'CCDC 2108166'
loop_
_audit_author_name
_audit_author_address
'Hui Liang'
;Lanzhou University
China
;
_audit_update_record             
;
2021-09-07 deposited with the CCDC.	2021-12-30 downloaded from the CCDC.
;
_audit_creation_date             2021-07-06
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H26 N2 O3'
_chemical_formula_sum            'C23 H26 N2 O3'
_chemical_formula_weight         378.46
_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'
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           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                   9.42390(10)
_cell_length_b                   10.06990(10)
_cell_length_c                   11.23500(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.7120(10)
_cell_angle_gamma                90
_cell_volume                     1035.789(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9557
_cell_measurement_temperature    298.30(10)
_cell_measurement_theta_max      77.3440
_cell_measurement_theta_min      4.8360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
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    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11587
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.509
_diffrn_reflns_theta_min         4.830
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.30(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     93.00 174.00   0.50    0.05    --  107.75  77.00-120.00  162
  2  ω     98.00 170.00   0.50    0.05    --  107.75  37.00-180.00  144
  3  ω    111.00 171.00   0.50    0.05    --  107.75  37.00-150.00  120
  4  ω    124.00 150.00   0.50    0.05    --  107.75  37.00-120.00   52
  5  ω     97.00 123.00   0.50    0.05    --  107.75  37.00-120.00   52
  6  ω    139.00 172.00   0.50    0.05    --  107.75  37.00  60.00   66
  7  ω    100.00 135.00   0.50    0.05    --  107.75  37.00  60.00   70
  8  ω    142.00 175.00   0.50    0.05    --  107.75  83.00 -85.00   66
  9  ω     38.00  63.00   0.50    0.05    --  107.75 -57.00-150.00   50
 10  ω    -27.00   8.00   0.50    0.05    --   47.57 -19.00-180.00   70
 11  ω    -26.00  19.00   0.50    0.05    --   47.57 -19.00-120.00   90
 12  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00 -60.00   50
 13  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00   0.00   50
 14  ω     38.00  63.00   0.50    0.05    --  107.75 -57.00  30.00   50
 15  ω     63.00  94.00   0.50    0.05    --   47.57-125.00  60.00   62
 16  ω     31.00  56.00   0.50    0.05    --   47.57-125.00  60.00   50
 17  ω     -5.00  41.00   0.50    0.05    --   47.57 -83.00 153.00   92
 18  ω     60.00  85.00   0.50    0.05    --  107.75 -83.00 153.00   50
 19  ω     80.00 106.00   0.50    0.05    --  107.75 -99.00 120.00   52
 20  ω     64.00  99.00   0.50    0.05    --  107.75 -99.00 -90.00   70
 21  ω     58.00  99.00   0.50    0.05    --  107.75 -99.00-120.00   82
 22  ω    -62.00 -18.00   0.50    0.05    --  -47.57  83.00 -85.00   88
 23  ω    -15.00  12.00   0.50    0.05    --  -47.57  83.00 -85.00   54
 24  ω   -106.00 -80.00   0.50    0.05    -- -100.00  83.00 -85.00   52
 25  ω   -106.00 -27.00   0.50    0.05    -- -100.00 125.00 150.00  158
 26  ω    -58.00 -30.00   0.50    0.05    -- -100.00  57.00 120.00   56
 27  ω    -58.00 -28.00   0.50    0.05    -- -100.00  57.00  90.00   60
 28  ω    -61.00 -28.00   0.50    0.05    --  -47.57  57.00 120.00   66
 29  ω    -18.00  21.00   0.50    0.05    --  -47.57  57.00 120.00   78
 30  ω   -109.00 -83.00   0.50    0.05    -- -100.00  77.00-150.00   52
 31  ω    -68.00 -42.00   0.50    0.05    -- -100.00  57.00-150.00   52
 32  ω    -53.00 -28.00   0.50    0.05    -- -100.00  77.00-150.00   50
 33  ω   -175.00-129.00   0.50    0.05    -- -100.00 -19.00  60.00   92
 34  ω   -122.00 -85.00   0.50    0.05    -- -100.00 -77.00  90.00   74
 35  ω   -111.00 -25.00   0.50    0.05    --  -47.57 -77.00 120.00  172
 36  ω   -121.00 -81.00   0.50    0.05    -- -100.00 -77.00 120.00   80
 37  ω   -170.00-137.00   0.50    0.05    -- -100.00 -77.00  90.00   66
 38  ω   -169.00-127.00   0.50    0.05    -- -100.00 -37.00  30.00   84
 39  ω   -123.00 -87.00   0.50    0.05    -- -100.00 -37.00  30.00   72
 40  ω   -169.00-136.00   0.50    0.05    -- -100.00 -77.00 120.00   66
 41  ω   -173.00 -84.00   0.50    0.05    -- -100.00 -83.00 153.00  178
;
_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      0.0456165000
_diffrn_orient_matrix_UB_12      -0.1093028000
_diffrn_orient_matrix_UB_13      -0.0793717000
_diffrn_orient_matrix_UB_21      0.0717387000
_diffrn_orient_matrix_UB_22      -0.0782647000
_diffrn_orient_matrix_UB_23      0.1165520000
_diffrn_orient_matrix_UB_31      -0.1452222000
_diffrn_orient_matrix_UB_32      -0.0730220000
_diffrn_orient_matrix_UB_33      -0.0061477000
_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         0.837
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                3994
_reflns_number_total             4103
_reflns_odcompleteness_completeness 98.22
_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 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_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         0.157
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1770 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.113
_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)+(0.0526P)²+0.0654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0884
_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. Restrained distances
 C20-C23 \\sim C20-C24
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.005
4. Others
 Fixed Sof: C23(0.6) H23A(0.6) H23B(0.6) H23C(0.6) C24(0.4) H24A(0.4)
 H24B(0.4) H24C(0.4)
5.a Ternary CH refined with riding coordinates:
 C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C8(H8), C14(H14), C2(H2A), C3(H3), C4(H4), C18(H18), C15(H15),
  C16(H16), C17(H17)
5.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
;
_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 0.40529(18) 0.72717(13) 0.75417(12) 0.0488(3) Uani 1 1 d . . . . .
O2 O 0.3836(2) 0.55714(15) 0.88146(13) 0.0571(4) Uani 1 1 d . . . . .
O3 O 0.58965(16) 0.15753(18) 0.54719(14) 0.0580(4) Uani 1 1 d . . . . .
N1 N 0.33275(16) 0.53117(14) 0.67552(14) 0.0367(3) Uani 1 1 d . . . . .
N2 N -0.09794(18) 0.34538(19) 0.47844(16) 0.0496(4) Uani 1 1 d . . . . .
H2 H -0.160836 0.309871 0.418821 0.060 Uiso 1 1 calc R . . . .
C19 C 0.37583(19) 0.60025(17) 0.77973(16) 0.0364(4) Uani 1 1 d . . . . .
C6 C -0.1281(2) 0.43932(19) 0.55710(17) 0.0418(4) Uani 1 1 d . . . . .
C1 C 0.00467(19) 0.47100(18) 0.64067(17) 0.0379(4) Uani 1 1 d . . . . .
C5 C -0.2602(2) 0.4982(2) 0.5634(2) 0.0487(5) Uani 1 1 d . . . . .
H5 H -0.346716 0.477318 0.507033 0.058 Uiso 1 1 calc R . . . .
C12 C 0.6274(2) 0.20519(18) 0.64902(17) 0.0398(4) Uani 1 1 d . . . . .
C7 C 0.11686(19) 0.39196(17) 0.60741(18) 0.0383(4) Uani 1 1 d . . . . .
C13 C 0.7766(2) 0.1802(2) 0.72648(18) 0.0442(4) Uani 1 1 d . . . . .
C10 C 0.3709(2) 0.29998(19) 0.61989(18) 0.0422(4) Uani 1 1 d . . . . .
H10A H 0.326278 0.212605 0.611039 0.051 Uiso 1 1 calc R . . . .
H10B H 0.375851 0.330564 0.539103 0.051 Uiso 1 1 calc R . . . .
C9 C 0.27601(19) 0.39519(16) 0.67314(17) 0.0361(4) Uani 1 1 d . . . . .
H9 H 0.282856 0.368379 0.758170 0.043 Uiso 1 1 calc R . . . .
C8 C 0.0496(2) 0.3168(2) 0.51012(19) 0.0478(4) Uani 1 1 d . . . . .
H8 H 0.095913 0.255119 0.470631 0.057 Uiso 1 1 calc R . . . .
C14 C 0.8395(3) 0.2577(2) 0.8270(2) 0.0565(5) Uani 1 1 d . . . . .
H14 H 0.787579 0.328918 0.848049 0.068 Uiso 1 1 calc R . . . .
C11 C 0.5243(2) 0.29007(17) 0.70064(17) 0.0393(4) Uani 1 1 d . . . . .
H11A H 0.564807 0.378826 0.714607 0.047 Uiso 1 1 calc R . . . .
H11B H 0.518531 0.254057 0.779437 0.047 Uiso 1 1 calc R . . . .
C2 C 0.0034(2) 0.5613(2) 0.73483(19) 0.0453(4) Uani 1 1 d . . . . .
H2A H 0.089082 0.582352 0.792096 0.054 Uiso 1 1 calc R . . . .
C3 C -0.1278(2) 0.6188(2) 0.7412(2) 0.0545(5) Uani 1 1 d . . . . .
H3 H -0.129772 0.679126 0.803404 0.065 Uiso 1 1 calc R . . . .
C20 C 0.4617(2) 0.82085(19) 0.85494(18) 0.0485(5) Uani 1 1 d D . . . .
C4 C -0.2581(2) 0.5879(2) 0.6557(2) 0.0547(5) Uani 1 1 d . . . . .
H4 H -0.344459 0.629066 0.661657 0.066 Uiso 1 1 calc R . . . .
C21 C 0.3496(3) 0.8414(3) 0.9298(3) 0.0715(7) Uani 1 1 d . . . . .
H21A H 0.259119 0.869958 0.877103 0.107 Uiso 1 1 calc GR . . . .
H21B H 0.384005 0.907924 0.991127 0.107 Uiso 1 1 calc GR . . . .
H21C H 0.334671 0.759502 0.968795 0.107 Uiso 1 1 calc GR . . . .
C22 C 0.6036(3) 0.7720(3) 0.9351(3) 0.0757(8) Uani 1 1 d . . . . .
H22A H 0.584816 0.698374 0.983361 0.114 Uiso 1 1 calc GR . . . .
H22B H 0.649078 0.842408 0.988288 0.114 Uiso 1 1 calc GR . . . .
H22C H 0.667354 0.744256 0.884642 0.114 Uiso 1 1 calc GR . . . .
C18 C 0.8575(3) 0.0769(4) 0.6963(3) 0.0883(11) Uani 1 1 d . . . . .
H18 H 0.818756 0.025218 0.627679 0.106 Uiso 1 1 calc R . . . .
C15 C 0.9777(3) 0.2307(4) 0.8962(3) 0.0786(8) Uani 1 1 d . . . . .
H15 H 1.019075 0.283915 0.963119 0.094 Uiso 1 1 calc R . . . .
C16 C 1.0543(4) 0.1250(5) 0.8661(4) 0.1112(15) Uani 1 1 d . . . . .
H16 H 1.146716 0.104819 0.913707 0.133 Uiso 1 1 calc R . . . .
C17 C 0.9942(4) 0.0499(5) 0.7661(4) 0.132(2) Uani 1 1 d . . . . .
H17 H 1.046763 -0.020883 0.745070 0.159 Uiso 1 1 calc R . . . .
C23 C 0.4559(8) 0.9528(5) 0.7869(6) 0.0655(14) Uani 0.6 1 d D U P A 1
H23A H 0.511778 0.945906 0.725986 0.098 Uiso 0.6 1 calc GR . P A 1
H23B H 0.496016 1.021761 0.844024 0.098 Uiso 0.6 1 calc GR . P A 1
H23C H 0.356326 0.973656 0.748035 0.098 Uiso 0.6 1 calc GR . P A 1
H1 H 0.332(3) 0.569(3) 0.607(2) 0.047(6) Uiso 1 1 d . . . . .
C24 C 0.5280(13) 0.9340(10) 0.7898(10) 0.078(3) Uani 0.4 1 d D U P A 2
H24A H 0.607275 0.899283 0.759215 0.116 Uiso 0.4 1 calc GR . P A 2
H24B H 0.563275 1.003944 0.847340 0.116 Uiso 0.4 1 calc GR . P A 2
H24C H 0.454034 0.968448 0.722988 0.116 Uiso 0.4 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.353(2) . ?
O1 C20 1.473(2) . ?
O2 C19 1.208(2) . ?
O3 C12 1.214(2) . ?
N1 C19 1.340(2) . ?
N1 C9 1.468(2) . ?
N1 H1 0.86(3) . ?
N2 H2 0.8600 . ?
N2 C6 1.369(3) . ?
N2 C8 1.381(3) . ?
C6 C1 1.411(3) . ?
C6 C5 1.396(3) . ?
C1 C7 1.442(3) . ?
C1 C2 1.397(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.372(3) . ?
C12 C13 1.489(3) . ?
C12 C11 1.509(2) . ?
C7 C9 1.507(2) . ?
C7 C8 1.357(3) . ?
C13 C14 1.385(3) . ?
C13 C18 1.378(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.527(2) . ?
C10 C11 1.517(3) . ?
C9 H9 0.9800 . ?
C8 H8 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.377(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C2 H2A 0.9300 . ?
C2 C3 1.382(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.402(3) . ?
C20 C21 1.513(3) . ?
C20 C22 1.506(4) . ?
C20 C23 1.527(6) . ?
C20 C24 1.562(10) . ?
C4 H4 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C18 H18 0.9300 . ?
C18 C17 1.368(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.373(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.361(5) . ?
C17 H17 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C19 O1 C20 119.78(14) . . ?
C19 N1 C9 122.27(15) . . ?
C19 N1 H1 119.0(17) . . ?
C9 N1 H1 118.6(17) . . ?
C6 N2 H2 125.4 . . ?
C6 N2 C8 109.14(16) . . ?
C8 N2 H2 125.4 . . ?
O2 C19 O1 124.79(17) . . ?
O2 C19 N1 125.31(17) . . ?
N1 C19 O1 109.87(15) . . ?
N2 C6 C1 107.38(16) . . ?
N2 C6 C5 130.55(19) . . ?
C5 C6 C1 122.06(19) . . ?
C6 C1 C7 106.96(16) . . ?
C2 C1 C6 119.04(17) . . ?
C2 C1 C7 133.96(17) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 C6 117.67(19) . . ?
C4 C5 H5 121.2 . . ?
O3 C12 C13 120.60(17) . . ?
O3 C12 C11 120.97(17) . . ?
C13 C12 C11 118.43(16) . . ?
C1 C7 C9 124.54(16) . . ?
C8 C7 C1 106.59(16) . . ?
C8 C7 C9 128.87(17) . . ?
C14 C13 C12 122.91(18) . . ?
C18 C13 C12 119.0(2) . . ?
C18 C13 C14 118.1(2) . . ?
H10A C10 H10B 107.9 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C11 C10 C9 111.75(14) . . ?
N1 C9 C7 110.18(14) . . ?
N1 C9 C10 110.38(14) . . ?
N1 C9 H9 107.4 . . ?
C7 C9 C10 113.69(14) . . ?
C7 C9 H9 107.4 . . ?
C10 C9 H9 107.4 . . ?
N2 C8 H8 125.0 . . ?
C7 C8 N2 109.93(18) . . ?
C7 C8 H8 125.0 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.5 . . ?
C12 C11 C10 114.61(15) . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 C1 118.68(19) . . ?
C3 C2 H2A 120.7 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
O1 C20 C21 110.05(18) . . ?
O1 C20 C22 110.99(18) . . ?
O1 C20 C23 102.1(3) . . ?
O1 C20 C24 102.7(4) . . ?
C21 C20 C23 102.2(3) . . ?
C21 C20 C24 124.7(5) . . ?
C22 C20 C21 110.5(2) . . ?
C22 C20 C23 120.3(3) . . ?
C22 C20 C24 97.0(5) . . ?
C5 C4 C3 121.15(19) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C18 C17 H17 119.5 . . ?
C16 C17 C18 120.9(3) . . ?
C16 C17 H17 119.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O3 C12 C13 C14 162.2(2) . . . . ?
O3 C12 C13 C18 -16.6(3) . . . . ?
O3 C12 C11 C10 4.7(3) . . . . ?
N2 C6 C1 C7 0.54(19) . . . . ?
N2 C6 C1 C2 -177.35(17) . . . . ?
N2 C6 C5 C4 178.1(2) . . . . ?
C19 O1 C20 C21 -63.5(3) . . . . ?
C19 O1 C20 C22 59.2(3) . . . . ?
C19 O1 C20 C23 -171.5(3) . . . . ?
C19 O1 C20 C24 161.8(5) . . . . ?
C19 N1 C9 C7 113.43(18) . . . . ?
C19 N1 C9 C10 -120.18(18) . . . . ?
C6 N2 C8 C7 -0.8(2) . . . . ?
C6 C1 C7 C9 179.88(16) . . . . ?
C6 C1 C7 C8 -1.0(2) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C6 C5 C4 C3 -0.4(3) . . . . ?
C1 C6 C5 C4 -0.9(3) . . . . ?
C1 C7 C9 N1 -56.3(2) . . . . ?
C1 C7 C9 C10 179.19(17) . . . . ?
C1 C7 C8 N2 1.1(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C5 C6 C1 C7 179.73(17) . . . . ?
C5 C6 C1 C2 1.8(3) . . . . ?
C12 C13 C14 C15 179.9(2) . . . . ?
C12 C13 C18 C17 -179.1(4) . . . . ?
C7 C1 C2 C3 -178.6(2) . . . . ?
C13 C12 C11 C10 -174.84(16) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C13 C18 C17 C16 -0.8(8) . . . . ?
C9 N1 C19 O1 -172.25(15) . . . . ?
C9 N1 C19 O2 5.9(3) . . . . ?
C9 C7 C8 N2 -179.83(18) . . . . ?
C9 C10 C11 C12 -175.80(15) . . . . ?
C8 N2 C6 C1 0.1(2) . . . . ?
C8 N2 C6 C5 -179.0(2) . . . . ?
C8 C7 C9 N1 124.8(2) . . . . ?
C8 C7 C9 C10 0.3(3) . . . . ?
C14 C13 C18 C17 2.0(6) . . . . ?
C14 C15 C16 C17 1.7(7) . . . . ?
C11 C12 C13 C14 -18.3(3) . . . . ?
C11 C12 C13 C18 162.9(3) . . . . ?
C11 C10 C9 N1 64.85(19) . . . . ?
C11 C10 C9 C7 -170.75(15) . . . . ?
C2 C1 C7 C9 -2.7(3) . . . . ?
C2 C1 C7 C8 176.4(2) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C20 O1 C19 O2 4.8(3) . . . . ?
C20 O1 C19 N1 -177.02(16) . . . . ?
C18 C13 C14 C15 -1.3(4) . . . . ?
C15 C16 C17 C18 -1.0(9) . . . . ?

_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 1.312
_oxdiff_exptl_absorpt_empirical_full_min 0.834
