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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_dd105-1
_database_code_depnum_ccdc_archive 'CCDC 2156622'
loop_
_audit_author_name
_audit_author_address
'Rao Weidong'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-03-05 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2021-06-20
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H23 N O3'
_chemical_formula_sum            'C24 H23 N O3'
_chemical_formula_weight         373.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.7477(8)
_cell_length_b                   21.8900(14)
_cell_length_c                   14.6259(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.106(7)
_cell_angle_gamma                90
_cell_volume                     4070.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4101
_cell_measurement_temperature    150.1(3)
_cell_measurement_theta_max      26.0850
_cell_measurement_theta_min      2.8790
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_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  0.0531
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18529
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.199
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.1(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  27.00   1.00    5.00    --  -11.27 -99.00 -30.00   45
  2  ω    -27.00  86.00   1.00    5.00    --   11.90  19.00 -90.00  113
  3  ω     19.00  69.00   1.00    5.00    --   11.90  38.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0012703000
_diffrn_orient_matrix_UB_12      0.0189989000
_diffrn_orient_matrix_UB_13      0.0393088000
_diffrn_orient_matrix_UB_21      0.0162489000
_diffrn_orient_matrix_UB_22      0.0249987000
_diffrn_orient_matrix_UB_23      -0.0264844000
_diffrn_orient_matrix_UB_31      -0.0533607000
_diffrn_orient_matrix_UB_32      0.0080248000
_diffrn_orient_matrix_UB_33      -0.0107573000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4846
_reflns_number_total             7162
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7162
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0624
_refine_ls_restrained_S_all      1.102
_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)+(0.0702P)²+0.8541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1660
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C22, C23, C24
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C22 \\sim C23 \\sim C24: within 2A with sigma of 0.002 and sigma for terminal
atoms of 0.004 within 2A
4.a Ternary CH refined with riding coordinates:
 C9(H9), C13(H13), C14(H14), C21(H21), C33(H33), C37(H37), C38(H38), C45(H45)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,
 H24B), C35(H35A,H35B), C36(H36A,H36B), C46(H46A,H46B), C47(H47A,H47B),
 C48(H48A,H48B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C17(H17), C18(H18), C19(H19),
 C20(H20), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C41(H41), C42(H42),
  C43(H43), C44(H44)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.40153(17) 0.35248(11) 0.70050(17) 0.0681(7) Uani 1 1 d . . . . .
O2 O 0.27997(12) 0.36728(7) 0.81035(12) 0.0350(4) Uani 1 1 d . . . . .
O3 O 0.12117(16) 0.20082(9) 0.87918(15) 0.0550(6) Uani 1 1 d . . . . .
N1 N 0.08124(15) 0.29444(9) 0.82170(16) 0.0343(5) Uani 1 1 d . . . . .
C1 C 0.22236(19) 0.47504(11) 0.80302(19) 0.0349(6) Uani 1 1 d . . . . .
C2 C 0.26093(19) 0.52391(12) 0.7559(2) 0.0397(7) Uani 1 1 d . . . . .
H2 H 0.289684 0.516572 0.700315 0.048 Uiso 1 1 calc R U . . .
C3 C 0.2586(2) 0.58284(13) 0.7878(2) 0.0520(8) Uani 1 1 d . . . . .
H3 H 0.283726 0.614847 0.753733 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2182(3) 0.59377(14) 0.8716(3) 0.0592(9) Uani 1 1 d . . . . .
H4 H 0.215982 0.633335 0.894557 0.071 Uiso 1 1 calc R U . . .
C5 C 0.1815(2) 0.54588(13) 0.9206(2) 0.0529(8) Uani 1 1 d . . . . .
H5 H 0.156395 0.553656 0.977655 0.063 Uiso 1 1 calc R U . . .
C6 C 0.1803(2) 0.48573(12) 0.8881(2) 0.0402(7) Uani 1 1 d . . . . .
C7 C 0.1368(2) 0.43852(13) 0.9454(2) 0.0429(7) Uani 1 1 d . . . . .
H7 H 0.143284 0.446818 1.007952 0.051 Uiso 1 1 calc R U . . .
C8 C 0.08951(19) 0.38571(12) 0.9234(2) 0.0389(7) Uani 1 1 d . . . . .
C9 C 0.06095(18) 0.36155(11) 0.82869(18) 0.0328(6) Uani 1 1 d . . . . .
H9 H -0.015392 0.366530 0.818512 0.039 Uiso 1 1 calc R U . . .
C10 C 0.0527(2) 0.34288(14) 0.9947(2) 0.0506(8) Uani 1 1 d . . . . .
H10A H -0.022950 0.337838 0.986088 0.061 Uiso 1 1 calc R U . . .
H10B H 0.069295 0.359827 1.055331 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1064(2) 0.28122(14) 0.9870(2) 0.0531(8) Uani 1 1 d . . . . .
H11A H 0.179365 0.285337 1.009784 0.064 Uiso 1 1 calc R U . . .
H11B H 0.073491 0.252396 1.026462 0.064 Uiso 1 1 calc R U . . .
C12 C 0.1029(2) 0.25510(13) 0.8921(2) 0.0404(7) Uani 1 1 d . . . . .
C13 C 0.21977(18) 0.41273(11) 0.75865(19) 0.0329(6) Uani 1 1 d . . . . .
H13 H 0.248851 0.416595 0.698681 0.040 Uiso 1 1 calc R U . . .
C14 C 0.10769(18) 0.38809(11) 0.74331(18) 0.0315(6) Uani 1 1 d . . . . .
H14 H 0.061586 0.420578 0.717660 0.038 Uiso 1 1 calc R U . . .
C15 C 0.10162(17) 0.33414(11) 0.67935(18) 0.0300(6) Uani 1 1 d . . . . .
C16 C 0.08792(18) 0.28044(11) 0.72737(19) 0.0319(6) Uani 1 1 d . . . . .
C17 C 0.0796(2) 0.22431(12) 0.6838(2) 0.0411(7) Uani 1 1 d . . . . .
H17 H 0.070489 0.188494 0.716523 0.049 Uiso 1 1 calc R U . . .
C18 C 0.0854(2) 0.22359(13) 0.5892(2) 0.0454(7) Uani 1 1 d . . . . .
H18 H 0.079734 0.186626 0.557846 0.054 Uiso 1 1 calc R U . . .
C19 C 0.0993(2) 0.27690(12) 0.5410(2) 0.0419(7) Uani 1 1 d . . . . .
H19 H 0.102314 0.275416 0.477656 0.050 Uiso 1 1 calc R U . . .
C20 C 0.10892(19) 0.33255(12) 0.58589(19) 0.0356(6) Uani 1 1 d . . . . .
H20 H 0.120107 0.368240 0.553476 0.043 Uiso 1 1 calc R U . . .
C21 C 0.3875(2) 0.36536(13) 0.7930(2) 0.0479(8) Uani 1 1 d . . . . .
H21 H 0.422490 0.403682 0.811726 0.057 Uiso 1 1 calc R U . . .
C22 C 0.4360(3) 0.31194(15) 0.8472(3) 0.0666(8) Uani 1 1 d . U . . .
H22A H 0.510674 0.317968 0.861788 0.080 Uiso 1 1 calc R U . . .
H22B H 0.401503 0.305163 0.903302 0.080 Uiso 1 1 calc R U . . .
C23 C 0.4156(4) 0.26044(18) 0.7806(3) 0.0921(9) Uani 1 1 d . U . . .
H23A H 0.475721 0.233192 0.782185 0.111 Uiso 1 1 calc R U . . .
H23B H 0.354535 0.237225 0.796041 0.111 Uiso 1 1 calc R U . . .
C24 C 0.3971(3) 0.28782(18) 0.6888(3) 0.0876(10) Uani 1 1 d . U . . .
H24A H 0.450564 0.274466 0.649206 0.105 Uiso 1 1 calc R U . . .
H24B H 0.328776 0.275717 0.661235 0.105 Uiso 1 1 calc R U . . .
O4 O 0.15586(14) 0.47325(8) 0.54776(14) 0.0466(5) Uani 1 1 d . . . . .
O5 O 0.18428(12) 0.54007(7) 0.29233(12) 0.0303(4) Uani 1 1 d . . . . .
O6 O 0.20390(14) 0.46265(8) 0.18469(13) 0.0444(5) Uani 1 1 d . . . . .
N2 N 0.26880(15) 0.53767(8) 0.48431(14) 0.0297(5) Uani 1 1 d . . . . .
C25 C 0.24420(17) 0.63554(11) 0.22611(18) 0.0294(6) Uani 1 1 d . . . . .
C26 C 0.25957(19) 0.64505(12) 0.13323(19) 0.0361(6) Uani 1 1 d . . . . .
H26 H 0.287898 0.613715 0.099814 0.043 Uiso 1 1 calc R U . . .
C27 C 0.2339(2) 0.69937(13) 0.0902(2) 0.0459(7) Uani 1 1 d . . . . .
H27 H 0.243742 0.704185 0.028218 0.055 Uiso 1 1 calc R U . . .
C28 C 0.1938(2) 0.74663(13) 0.1389(2) 0.0467(8) Uani 1 1 d . . . . .
H28 H 0.177836 0.783826 0.110447 0.056 Uiso 1 1 calc R U . . .
C29 C 0.1773(2) 0.73830(12) 0.2305(2) 0.0406(7) Uani 1 1 d . . . . .
H29 H 0.149300 0.770247 0.262832 0.049 Uiso 1 1 calc R U . . .
C30 C 0.20159(18) 0.68328(11) 0.27606(18) 0.0319(6) Uani 1 1 d . . . . .
C31 C 0.17287(18) 0.67848(11) 0.37155(18) 0.0310(6) Uani 1 1 d . . . . .
H31 H 0.121915 0.706284 0.387064 0.037 Uiso 1 1 calc R U . . .
C32 C 0.20669(17) 0.64155(10) 0.43958(18) 0.0283(6) Uani 1 1 d . . . . .
C33 C 0.29565(18) 0.59730(10) 0.44187(18) 0.0295(6) Uani 1 1 d . . . . .
H33 H 0.351547 0.615203 0.482916 0.035 Uiso 1 1 calc R U . . .
C34 C 0.17864(19) 0.52505(12) 0.52500(18) 0.0335(6) Uani 1 1 d . . . . .
C35 C 0.1082(2) 0.57821(12) 0.5423(2) 0.0401(7) Uani 1 1 d . . . . .
H35A H 0.087474 0.575380 0.604697 0.048 Uiso 1 1 calc R U . . .
H35B H 0.044963 0.574684 0.501698 0.048 Uiso 1 1 calc R U . . .
C36 C 0.15583(19) 0.64104(11) 0.52907(18) 0.0353(6) Uani 1 1 d . . . . .
H36A H 0.101400 0.672026 0.528585 0.042 Uiso 1 1 calc R U . . .
H36B H 0.207749 0.649897 0.579062 0.042 Uiso 1 1 calc R U . . .
C37 C 0.27438(18) 0.57471(11) 0.26799(18) 0.0309(6) Uani 1 1 d . . . . .
H37 H 0.310184 0.551123 0.222541 0.037 Uiso 1 1 calc R U . . .
C38 C 0.34800(18) 0.57901(11) 0.35480(18) 0.0302(6) Uani 1 1 d . . . . .
H38 H 0.405894 0.607113 0.344730 0.036 Uiso 1 1 calc R U . . .
C39 C 0.39145(18) 0.51680(11) 0.38119(18) 0.0318(6) Uani 1 1 d . . . . .
C40 C 0.33955(18) 0.49323(11) 0.45362(18) 0.0321(6) Uani 1 1 d . . . . .
C41 C 0.3610(2) 0.43500(11) 0.4877(2) 0.0386(7) Uani 1 1 d . . . . .
H41 H 0.326250 0.419345 0.536326 0.046 Uiso 1 1 calc R U . . .
C42 C 0.4366(2) 0.40103(12) 0.4461(2) 0.0413(7) Uani 1 1 d . . . . .
H42 H 0.452459 0.361805 0.467304 0.050 Uiso 1 1 calc R U . . .
C43 C 0.4887(2) 0.42430(12) 0.3740(2) 0.0439(7) Uani 1 1 d . . . . .
H43 H 0.538962 0.400712 0.347290 0.053 Uiso 1 1 calc R U . . .
C44 C 0.4664(2) 0.48254(12) 0.3415(2) 0.0415(7) Uani 1 1 d . . . . .
H44 H 0.501728 0.498371 0.293333 0.050 Uiso 1 1 calc R U . . .
C45 C 0.13442(19) 0.50438(11) 0.22149(18) 0.0336(6) Uani 1 1 d . . . . .
H45 H 0.101266 0.530479 0.173245 0.040 Uiso 1 1 calc R U . . .
C46 C 0.0530(2) 0.46567(11) 0.2647(2) 0.0421(7) Uani 1 1 d . . . . .
H46A H -0.002666 0.453400 0.219755 0.051 Uiso 1 1 calc R U . . .
H46B H 0.022554 0.487243 0.314286 0.051 Uiso 1 1 calc R U . . .
C47 C 0.1173(2) 0.41094(13) 0.3001(3) 0.0561(9) Uani 1 1 d . . . . .
H47A H 0.140291 0.416152 0.364320 0.067 Uiso 1 1 calc R U . . .
H47B H 0.076426 0.373626 0.293173 0.067 Uiso 1 1 calc R U . . .
C48 C 0.2100(2) 0.40917(12) 0.2418(2) 0.0488(8) Uani 1 1 d . . . . .
H48A H 0.275222 0.409115 0.280244 0.059 Uiso 1 1 calc R U . . .
H48B H 0.207551 0.372566 0.204330 0.059 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 C21 1.406(4) . ?
O1 C24 1.427(4) . ?
O2 C13 1.438(3) . ?
O2 C21 1.412(3) . ?
O3 C12 1.228(3) . ?
N1 C9 1.496(3) . ?
N1 C12 1.355(3) . ?
N1 C16 1.422(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.409(4) . ?
C1 C13 1.510(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.400(4) . ?
C6 C7 1.465(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.333(4) . ?
C8 C9 1.503(4) . ?
C8 C10 1.503(4) . ?
C9 H9 0.9800 . ?
C9 C14 1.536(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.521(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.500(4) . ?
C13 H13 0.9800 . ?
C13 C14 1.529(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.505(3) . ?
C15 C16 1.387(3) . ?
C15 C20 1.377(4) . ?
C16 C17 1.385(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.392(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9800 . ?
C21 C22 1.519(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.500(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.474(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
O4 C34 1.223(3) . ?
O5 C37 1.442(3) . ?
O5 C45 1.412(3) . ?
O6 C45 1.406(3) . ?
O6 C48 1.437(3) . ?
N2 C33 1.496(3) . ?
N2 C34 1.360(3) . ?
N2 C40 1.421(3) . ?
C25 C26 1.402(4) . ?
C25 C30 1.407(3) . ?
C25 C37 1.504(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.374(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.375(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.383(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.400(4) . ?
C30 C31 1.473(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.330(3) . ?
C32 C33 1.490(3) . ?
C32 C36 1.502(3) . ?
C33 H33 0.9800 . ?
C33 C38 1.533(3) . ?
C34 C35 1.502(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.521(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37 0.9800 . ?
C37 C38 1.527(4) . ?
C38 H38 0.9800 . ?
C38 C39 1.510(3) . ?
C39 C40 1.388(4) . ?
C39 C44 1.375(4) . ?
C40 C41 1.389(3) . ?
C41 H41 0.9300 . ?
C41 C42 1.391(4) . ?
C42 H42 0.9300 . ?
C42 C43 1.384(4) . ?
C43 H43 0.9300 . ?
C43 C44 1.383(4) . ?
C44 H44 0.9300 . ?
C45 H45 0.9800 . ?
C45 C46 1.512(4) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C46 C47 1.521(4) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C47 C48 1.507(4) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?

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
C21 O1 C24 107.9(3) . . ?
C21 O2 C13 114.49(19) . . ?
C12 N1 C9 126.8(2) . . ?
C12 N1 C16 125.2(2) . . ?
C16 N1 C9 107.5(2) . . ?
C2 C1 C6 118.9(2) . . ?
C2 C1 C13 118.9(3) . . ?
C6 C1 C13 122.1(2) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 C1 122.8(3) . . ?
C3 C2 H2 118.6 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.8(3) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.5(3) . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C7 124.9(2) . . ?
C5 C6 C1 117.4(3) . . ?
C5 C6 C7 117.7(3) . . ?
C6 C7 H7 114.5 . . ?
C8 C7 C6 131.1(3) . . ?
C8 C7 H7 114.5 . . ?
C7 C8 C9 127.1(3) . . ?
C7 C8 C10 122.1(3) . . ?
C10 C8 C9 110.7(2) . . ?
N1 C9 C8 112.1(2) . . ?
N1 C9 H9 105.9 . . ?
N1 C9 C14 103.69(19) . . ?
C8 C9 H9 105.9 . . ?
C8 C9 C14 122.3(2) . . ?
C14 C9 H9 105.9 . . ?
C8 C10 H10A 109.7 . . ?
C8 C10 H10B 109.7 . . ?
C8 C10 C11 109.7(2) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C10 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 C10 115.0(3) . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
O3 C12 N1 121.9(3) . . ?
O3 C12 C11 121.2(3) . . ?
N1 C12 C11 116.9(3) . . ?
O2 C13 C1 113.9(2) . . ?
O2 C13 H13 108.0 . . ?
O2 C13 C14 106.92(19) . . ?
C1 C13 H13 108.0 . . ?
C1 C13 C14 111.9(2) . . ?
C14 C13 H13 108.0 . . ?
C9 C14 H14 109.2 . . ?
C13 C14 C9 115.3(2) . . ?
C13 C14 H14 109.2 . . ?
C15 C14 C9 101.71(19) . . ?
C15 C14 C13 112.0(2) . . ?
C15 C14 H14 109.2 . . ?
C16 C15 C14 110.7(2) . . ?
C20 C15 C14 129.2(2) . . ?
C20 C15 C16 120.1(2) . . ?
C15 C16 N1 109.1(2) . . ?
C17 C16 N1 129.0(2) . . ?
C17 C16 C15 121.8(3) . . ?
C16 C17 H17 121.3 . . ?
C16 C17 C18 117.4(3) . . ?
C18 C17 H17 121.3 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.1(3) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.7(3) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 118.9(2) . . ?
C15 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
O1 C21 O2 111.8(2) . . ?
O1 C21 H21 110.7 . . ?
O1 C21 C22 105.8(3) . . ?
O2 C21 H21 110.7 . . ?
O2 C21 C22 107.1(2) . . ?
C22 C21 H21 110.7 . . ?
C21 C22 H22A 111.5 . . ?
C21 C22 H22B 111.5 . . ?
H22A C22 H22B 109.3 . . ?
C23 C22 C21 101.2(3) . . ?
C23 C22 H22A 111.5 . . ?
C23 C22 H22B 111.5 . . ?
C22 C23 H23A 110.3 . . ?
C22 C23 H23B 110.3 . . ?
H23A C23 H23B 108.5 . . ?
C24 C23 C22 107.2(3) . . ?
C24 C23 H23A 110.3 . . ?
C24 C23 H23B 110.3 . . ?
O1 C24 C23 106.9(4) . . ?
O1 C24 H24A 110.3 . . ?
O1 C24 H24B 110.3 . . ?
C23 C24 H24A 110.3 . . ?
C23 C24 H24B 110.3 . . ?
H24A C24 H24B 108.6 . . ?
C45 O5 C37 115.76(19) . . ?
C45 O6 C48 108.4(2) . . ?
C34 N2 C33 125.78(19) . . ?
C34 N2 C40 125.1(2) . . ?
C40 N2 C33 107.28(19) . . ?
C26 C25 C30 118.6(2) . . ?
C26 C25 C37 118.5(2) . . ?
C30 C25 C37 122.9(2) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 C25 121.8(3) . . ?
C27 C26 H26 119.1 . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.0(3) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.3 . . ?
C27 C28 C29 119.3(3) . . ?
C29 C28 H28 120.3 . . ?
C28 C29 H29 119.0 . . ?
C28 C29 C30 122.1(3) . . ?
C30 C29 H29 119.0 . . ?
C25 C30 C31 124.8(2) . . ?
C29 C30 C25 118.2(2) . . ?
C29 C30 C31 116.8(2) . . ?
C30 C31 H31 114.2 . . ?
C32 C31 C30 131.6(2) . . ?
C32 C31 H31 114.2 . . ?
C31 C32 C33 128.1(2) . . ?
C31 C32 C36 121.3(2) . . ?
C33 C32 C36 110.5(2) . . ?
N2 C33 H33 105.8 . . ?
N2 C33 C38 104.07(18) . . ?
C32 C33 N2 112.35(19) . . ?
C32 C33 H33 105.8 . . ?
C32 C33 C38 121.8(2) . . ?
C38 C33 H33 105.8 . . ?
O4 C34 N2 122.2(2) . . ?
O4 C34 C35 121.1(2) . . ?
N2 C34 C35 116.8(2) . . ?
C34 C35 H35A 108.4 . . ?
C34 C35 H35B 108.4 . . ?
C34 C35 C36 115.5(2) . . ?
H35A C35 H35B 107.5 . . ?
C36 C35 H35A 108.4 . . ?
C36 C35 H35B 108.4 . . ?
C32 C36 C35 108.6(2) . . ?
C32 C36 H36A 110.0 . . ?
C32 C36 H36B 110.0 . . ?
C35 C36 H36A 110.0 . . ?
C35 C36 H36B 110.0 . . ?
H36A C36 H36B 108.4 . . ?
O5 C37 C25 112.40(18) . . ?
O5 C37 H37 107.9 . . ?
O5 C37 C38 106.27(19) . . ?
C25 C37 H37 107.9 . . ?
C25 C37 C38 114.1(2) . . ?
C38 C37 H37 107.9 . . ?
C33 C38 H38 109.8 . . ?
C37 C38 C33 115.39(19) . . ?
C37 C38 H38 109.8 . . ?
C39 C38 C33 101.4(2) . . ?
C39 C38 C37 110.5(2) . . ?
C39 C38 H38 109.8 . . ?
C40 C39 C38 110.1(2) . . ?
C44 C39 C38 129.6(2) . . ?
C44 C39 C40 120.2(2) . . ?
C39 C40 N2 109.5(2) . . ?
C39 C40 C41 121.5(2) . . ?
C41 C40 N2 128.9(2) . . ?
C40 C41 H41 121.3 . . ?
C40 C41 C42 117.3(3) . . ?
C42 C41 H41 121.3 . . ?
C41 C42 H42 119.3 . . ?
C43 C42 C41 121.5(3) . . ?
C43 C42 H42 119.3 . . ?
C42 C43 H43 119.9 . . ?
C44 C43 C42 120.2(3) . . ?
C44 C43 H43 119.9 . . ?
C39 C44 C43 119.3(3) . . ?
C39 C44 H44 120.3 . . ?
C43 C44 H44 120.3 . . ?
O5 C45 H45 110.7 . . ?
O5 C45 C46 106.9(2) . . ?
O6 C45 O5 112.18(19) . . ?
O6 C45 H45 110.7 . . ?
O6 C45 C46 105.4(2) . . ?
C46 C45 H45 110.7 . . ?
C45 C46 H46A 111.3 . . ?
C45 C46 H46B 111.3 . . ?
C45 C46 C47 102.4(2) . . ?
H46A C46 H46B 109.2 . . ?
C47 C46 H46A 111.3 . . ?
C47 C46 H46B 111.3 . . ?
C46 C47 H47A 110.8 . . ?
C46 C47 H47B 110.8 . . ?
H47A C47 H47B 108.9 . . ?
C48 C47 C46 104.6(2) . . ?
C48 C47 H47A 110.8 . . ?
C48 C47 H47B 110.8 . . ?
O6 C48 C47 107.2(2) . . ?
O6 C48 H48A 110.3 . . ?
O6 C48 H48B 110.3 . . ?
C47 C48 H48A 110.3 . . ?
C47 C48 H48B 110.3 . . ?
H48A C48 H48B 108.5 . . ?

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 C21 C22 C23 -32.0(3) . . . . ?
O2 C13 C14 C9 47.0(3) . . . . ?
O2 C13 C14 C15 -68.6(3) . . . . ?
O2 C21 C22 C23 87.3(3) . . . . ?
N1 C9 C14 C13 -96.0(2) . . . . ?
N1 C9 C14 C15 25.4(2) . . . . ?
N1 C16 C17 C18 177.7(2) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C1 C6 C7 C8 -29.3(5) . . . . ?
C1 C13 C14 C9 -78.3(3) . . . . ?
C1 C13 C14 C15 166.0(2) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C2 C1 C6 C7 180.0(2) . . . . ?
C2 C1 C13 O2 120.5(2) . . . . ?
C2 C1 C13 C14 -118.1(3) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C3 C4 C5 C6 -1.8(5) . . . . ?
C4 C5 C6 C1 2.2(4) . . . . ?
C4 C5 C6 C7 -178.5(3) . . . . ?
C5 C6 C7 C8 151.5(3) . . . . ?
C6 C1 C2 C3 -1.1(4) . . . . ?
C6 C1 C13 O2 -63.8(3) . . . . ?
C6 C1 C13 C14 57.6(3) . . . . ?
C6 C7 C8 C9 -4.5(5) . . . . ?
C6 C7 C8 C10 178.5(3) . . . . ?
C7 C8 C9 N1 139.7(3) . . . . ?
C7 C8 C9 C14 15.7(4) . . . . ?
C7 C8 C10 C11 -121.0(3) . . . . ?
C8 C9 C14 C13 31.8(3) . . . . ?
C8 C9 C14 C15 153.2(2) . . . . ?
C8 C10 C11 C12 -49.1(3) . . . . ?
C9 N1 C12 O3 -178.0(2) . . . . ?
C9 N1 C12 C11 0.4(4) . . . . ?
C9 N1 C16 C15 15.8(3) . . . . ?
C9 N1 C16 C17 -162.2(2) . . . . ?
C9 C8 C10 C11 61.5(3) . . . . ?
C9 C14 C15 C16 -17.4(2) . . . . ?
C9 C14 C15 C20 163.4(2) . . . . ?
C10 C8 C9 N1 -43.0(3) . . . . ?
C10 C8 C9 C14 -167.0(2) . . . . ?
C10 C11 C12 O3 -163.3(2) . . . . ?
C10 C11 C12 N1 18.3(4) . . . . ?
C12 N1 C9 C8 12.4(3) . . . . ?
C12 N1 C9 C14 146.2(2) . . . . ?
C12 N1 C16 C15 -156.6(2) . . . . ?
C12 N1 C16 C17 25.4(4) . . . . ?
C13 O2 C21 O1 -60.1(3) . . . . ?
C13 O2 C21 C22 -175.5(2) . . . . ?
C13 C1 C2 C3 174.8(2) . . . . ?
C13 C1 C6 C5 -176.5(2) . . . . ?
C13 C1 C6 C7 4.3(4) . . . . ?
C13 C14 C15 C16 106.3(2) . . . . ?
C13 C14 C15 C20 -72.9(3) . . . . ?
C14 C15 C16 N1 1.6(3) . . . . ?
C14 C15 C16 C17 179.7(2) . . . . ?
C14 C15 C20 C19 -179.0(2) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 N1 C9 C8 -159.9(2) . . . . ?
C16 N1 C9 C14 -26.1(2) . . . . ?
C16 N1 C12 O3 -7.1(4) . . . . ?
C16 N1 C12 C11 171.3(2) . . . . ?
C16 C15 C20 C19 1.8(4) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
C18 C19 C20 C15 -1.6(4) . . . . ?
C20 C15 C16 N1 -179.2(2) . . . . ?
C20 C15 C16 C17 -1.0(4) . . . . ?
C21 O1 C24 C23 -18.7(4) . . . . ?
C21 O2 C13 C1 -86.2(3) . . . . ?
C21 O2 C13 C14 149.7(2) . . . . ?
C21 C22 C23 C24 20.4(4) . . . . ?
C22 C23 C24 O1 -2.4(5) . . . . ?
C24 O1 C21 O2 -83.9(3) . . . . ?
C24 O1 C21 C22 32.3(3) . . . . ?
O4 C34 C35 C36 167.8(2) . . . . ?
O5 C37 C38 C33 -47.2(3) . . . . ?
O5 C37 C38 C39 67.0(2) . . . . ?
O5 C45 C46 C47 -85.1(3) . . . . ?
O6 C45 C46 C47 34.4(3) . . . . ?
N2 C33 C38 C37 92.7(2) . . . . ?
N2 C33 C38 C39 -26.6(2) . . . . ?
N2 C34 C35 C36 -11.2(4) . . . . ?
N2 C40 C41 C42 -178.3(2) . . . . ?
C25 C26 C27 C28 1.2(4) . . . . ?
C25 C30 C31 C32 24.5(4) . . . . ?
C25 C37 C38 C33 77.3(3) . . . . ?
C25 C37 C38 C39 -168.56(19) . . . . ?
C26 C25 C30 C29 -0.5(3) . . . . ?
C26 C25 C30 C31 174.7(2) . . . . ?
C26 C25 C37 O5 -112.0(2) . . . . ?
C26 C25 C37 C38 126.9(2) . . . . ?
C26 C27 C28 C29 -1.5(4) . . . . ?
C27 C28 C29 C30 0.8(4) . . . . ?
C28 C29 C30 C25 0.2(4) . . . . ?
C28 C29 C30 C31 -175.4(2) . . . . ?
C29 C30 C31 C32 -160.3(3) . . . . ?
C30 C25 C26 C27 -0.2(4) . . . . ?
C30 C25 C37 O5 68.2(3) . . . . ?
C30 C25 C37 C38 -52.9(3) . . . . ?
C30 C31 C32 C33 7.9(4) . . . . ?
C30 C31 C32 C36 -173.0(2) . . . . ?
C31 C32 C33 N2 -137.3(3) . . . . ?
C31 C32 C33 C38 -13.0(4) . . . . ?
C31 C32 C36 C35 117.1(2) . . . . ?
C32 C33 C38 C37 -35.3(3) . . . . ?
C32 C33 C38 C39 -154.7(2) . . . . ?
C33 N2 C34 O4 170.4(2) . . . . ?
C33 N2 C34 C35 -10.5(4) . . . . ?
C33 N2 C40 C39 -13.1(3) . . . . ?
C33 N2 C40 C41 165.2(2) . . . . ?
C33 C32 C36 C35 -63.7(3) . . . . ?
C33 C38 C39 C40 20.1(2) . . . . ?
C33 C38 C39 C44 -163.5(3) . . . . ?
C34 N2 C33 C32 -6.0(3) . . . . ?
C34 N2 C33 C38 -139.7(2) . . . . ?
C34 N2 C40 C39 152.0(2) . . . . ?
C34 N2 C40 C41 -29.6(4) . . . . ?
C34 C35 C36 C32 47.4(3) . . . . ?
C36 C32 C33 N2 43.6(3) . . . . ?
C36 C32 C33 C38 167.9(2) . . . . ?
C37 O5 C45 O6 57.2(3) . . . . ?
C37 O5 C45 C46 172.26(19) . . . . ?
C37 C25 C26 C27 -180.0(2) . . . . ?
C37 C25 C30 C29 179.3(2) . . . . ?
C37 C25 C30 C31 -5.5(4) . . . . ?
C37 C38 C39 C40 -102.7(2) . . . . ?
C37 C38 C39 C44 73.7(3) . . . . ?
C38 C39 C40 N2 -5.0(3) . . . . ?
C38 C39 C40 C41 176.5(2) . . . . ?
C38 C39 C44 C43 -175.5(2) . . . . ?
C39 C40 C41 C42 -0.2(4) . . . . ?
C40 N2 C33 C32 159.0(2) . . . . ?
C40 N2 C33 C38 25.3(2) . . . . ?
C40 N2 C34 O4 8.0(4) . . . . ?
C40 N2 C34 C35 -173.0(2) . . . . ?
C40 C39 C44 C43 0.6(4) . . . . ?
C40 C41 C42 C43 0.3(4) . . . . ?
C41 C42 C43 C44 0.0(4) . . . . ?
C42 C43 C44 C39 -0.5(4) . . . . ?
C44 C39 C40 N2 178.2(2) . . . . ?
C44 C39 C40 C41 -0.3(4) . . . . ?
C45 O5 C37 C25 85.6(2) . . . . ?
C45 O5 C37 C38 -148.88(19) . . . . ?
C45 O6 C48 C47 16.6(3) . . . . ?
C45 C46 C47 C48 -23.7(3) . . . . ?
C46 C47 C48 O6 5.6(3) . . . . ?
C48 O6 C45 O5 83.6(2) . . . . ?
C48 O6 C45 C46 -32.3(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.500 203.4 51.5 ?
2 0.500 0.500 0.000 203.4 51.5 ?

_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 2.346
_oxdiff_exptl_absorpt_empirical_full_min 0.569
####################################################################### 
# 
# 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_296
_database_code_depnum_ccdc_archive 'CCDC 2156625'
loop_
_audit_author_name
_audit_author_address
'Rao Weidong'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-03-05 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2022-01-21
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N O3'
_chemical_formula_sum            'C23 H21 N O3'
_chemical_formula_weight         359.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.0345(10)
_cell_length_b                   11.2376(11)
_cell_length_c                   12.1940(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.022(7)
_cell_angle_gamma                90
_cell_volume                     1764.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2005
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      25.9890
_cell_measurement_theta_min      2.7360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7427
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.406
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  16.00   1.00    5.00    --  -11.35-107.00-107.00   27
  2  ω    -17.00  13.00   1.00    5.00    --  -11.35 -37.00-150.00   30
  3  ω    -35.00  64.00   1.00    5.00    --  -11.35  19.00-150.00   99
  4  ω    -77.00 -40.00   1.00    5.00    --  -11.35 -37.00-150.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0274872000
_diffrn_orient_matrix_UB_12      -0.0539793000
_diffrn_orient_matrix_UB_13      0.0132418000
_diffrn_orient_matrix_UB_21      -0.0458986000
_diffrn_orient_matrix_UB_22      -0.0268676000
_diffrn_orient_matrix_UB_23      0.0128170000
_diffrn_orient_matrix_UB_31      -0.0131132000
_diffrn_orient_matrix_UB_32      -0.0188219000
_diffrn_orient_matrix_UB_33      -0.0559134000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2292
_reflns_number_total             3121
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.054
_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)+(0.0401P)²+0.2463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1126
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10), C17(H17), C18(H18), C19(H19), C20(H20),
 C22(H22)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.11365(12) 0.47047(16) 0.79870(10) 0.0399(4) Uani 1 1 d . . . . .
O2 O 0.26522(10) 0.53161(14) 0.75212(9) 0.0289(4) Uani 1 1 d . . . . .
O3 O 0.43088(12) 0.48246(15) 0.23641(11) 0.0386(4) Uani 1 1 d . . . . .
N1 N 0.35604(12) 0.48303(16) 0.39213(11) 0.0229(4) Uani 1 1 d . . . . .
C1 C 0.16010(14) 0.6307(2) 0.59506(15) 0.0237(5) Uani 1 1 d . . . . .
C2 C 0.10647(15) 0.6289(2) 0.48559(15) 0.0252(5) Uani 1 1 d . . . . .
C3 C 0.04554(16) 0.7269(2) 0.44703(18) 0.0347(6) Uani 1 1 d . . . . .
H3 H 0.009254 0.726081 0.375003 0.042 Uiso 1 1 calc R U . . .
C4 C 0.03794(18) 0.8247(2) 0.5132(2) 0.0417(6) Uani 1 1 d . . . . .
H4 H -0.002772 0.889371 0.485867 0.050 Uiso 1 1 calc R U . . .
C5 C 0.09136(18) 0.8262(2) 0.62064(19) 0.0393(6) Uani 1 1 d . . . . .
H5 H 0.086364 0.891897 0.665850 0.047 Uiso 1 1 calc R U . . .
C6 C 0.22162(15) 0.5222(2) 0.63547(14) 0.0238(5) Uani 1 1 d . . . . .
H6 H 0.175510 0.452903 0.625365 0.029 Uiso 1 1 calc R U . . .
C7 C 0.31402(15) 0.49935(19) 0.57495(14) 0.0228(5) Uani 1 1 d . . . . .
H7 H 0.363804 0.449934 0.623575 0.027 Uiso 1 1 calc R U . . .
C8 C 0.28427(14) 0.4315(2) 0.46427(14) 0.0233(5) Uani 1 1 d . . . . .
H8 H 0.302250 0.347424 0.477333 0.028 Uiso 1 1 calc R U . . .
C9 C 0.17316(15) 0.4383(2) 0.40495(14) 0.0249(5) Uani 1 1 d . . . . .
C10 C 0.10419(15) 0.5245(2) 0.41331(15) 0.0270(5) Uani 1 1 d . . . . .
H10 H 0.042765 0.516741 0.363516 0.032 Uiso 1 1 calc R U . . .
C11 C 0.14273(17) 0.3372(2) 0.32498(17) 0.0358(6) Uani 1 1 d . . . . .
H11A H 0.069406 0.344636 0.295692 0.043 Uiso 1 1 calc R U . . .
H11B H 0.152122 0.262919 0.365820 0.043 Uiso 1 1 calc R U . . .
C12 C 0.20343(16) 0.3304(2) 0.22729(16) 0.0350(6) Uani 1 1 d . . . . .
H12A H 0.177947 0.263068 0.181128 0.042 Uiso 1 1 calc R U . . .
H12B H 0.189291 0.401732 0.182695 0.042 Uiso 1 1 calc R U . . .
C13 C 0.32115(16) 0.3178(2) 0.26040(16) 0.0310(5) Uani 1 1 d . . . . .
H13A H 0.335237 0.261761 0.321415 0.037 Uiso 1 1 calc R U . . .
H13B H 0.349962 0.285133 0.198175 0.037 Uiso 1 1 calc R U . . .
C14 C 0.37491(16) 0.4335(2) 0.29470(15) 0.0274(5) Uani 1 1 d . . . . .
C15 C 0.39641(14) 0.59242(19) 0.43739(14) 0.0217(5) Uani 1 1 d . . . . .
C16 C 0.37167(14) 0.60692(19) 0.54335(14) 0.0220(5) Uani 1 1 d . . . . .
C17 C 0.40301(15) 0.7074(2) 0.60445(15) 0.0272(5) Uani 1 1 d . . . . .
H17 H 0.387206 0.716488 0.675744 0.033 Uiso 1 1 calc R U . . .
C18 C 0.45830(16) 0.7948(2) 0.55861(16) 0.0301(5) Uani 1 1 d . . . . .
H18 H 0.479253 0.863207 0.598886 0.036 Uiso 1 1 calc R U . . .
C19 C 0.48232(15) 0.7800(2) 0.45251(16) 0.0291(5) Uani 1 1 d . . . . .
H19 H 0.519256 0.839154 0.422364 0.035 Uiso 1 1 calc R U . . .
C20 C 0.45239(15) 0.6787(2) 0.39039(15) 0.0252(5) Uani 1 1 d . . . . .
H20 H 0.469274 0.668875 0.319619 0.030 Uiso 1 1 calc R U . . .
C21 C 0.25840(19) 0.5078(3) 0.94176(16) 0.0469(7) Uani 1 1 d . . . . .
H21A H 0.327716 0.477876 0.944321 0.070 Uiso 1 1 calc R U . . .
H21B H 0.222585 0.461006 0.989691 0.070 Uiso 1 1 calc R U . . .
H21C H 0.261218 0.589186 0.965989 0.070 Uiso 1 1 calc R U . . .
C22 C 0.15191(16) 0.7304(2) 0.66077(17) 0.0314(5) Uani 1 1 d . . . . .
H22 H 0.187880 0.732505 0.732917 0.038 Uiso 1 1 calc R U . . .
C23 C 0.20211(17) 0.5006(2) 0.82599(15) 0.0289(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C23 1.198(2) . ?
O2 C6 1.450(2) . ?
O2 C23 1.357(2) . ?
O3 C14 1.226(2) . ?
N1 C8 1.498(2) . ?
N1 C14 1.369(2) . ?
N1 C15 1.415(3) . ?
C1 C2 1.407(3) . ?
C1 C6 1.500(3) . ?
C1 C22 1.391(3) . ?
C2 C3 1.395(3) . ?
C2 C10 1.465(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9300 . ?
C5 C22 1.378(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.530(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.546(3) . ?
C7 C16 1.505(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.516(3) . ?
C9 C10 1.336(3) . ?
C9 C11 1.509(3) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.532(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.531(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.505(3) . ?
C15 C16 1.389(2) . ?
C15 C20 1.390(3) . ?
C16 C17 1.379(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 C23 1.488(3) . ?
C22 H22 0.9300 . ?

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
C23 O2 C6 116.56(15) . . ?
C14 N1 C8 124.49(17) . . ?
C14 N1 C15 125.84(17) . . ?
C15 N1 C8 109.60(14) . . ?
C2 C1 C6 117.42(18) . . ?
C22 C1 C2 119.1(2) . . ?
C22 C1 C6 123.43(17) . . ?
C1 C2 C10 122.9(2) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 C10 118.19(17) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.9 . . ?
C22 C5 C4 120.1(2) . . ?
C22 C5 H5 119.9 . . ?
O2 C6 C1 111.74(16) . . ?
O2 C6 H6 108.6 . . ?
O2 C6 C7 105.56(14) . . ?
C1 C6 H6 108.6 . . ?
C1 C6 C7 113.52(16) . . ?
C7 C6 H6 108.6 . . ?
C6 C7 H7 107.5 . . ?
C6 C7 C8 113.30(15) . . ?
C8 C7 H7 107.5 . . ?
C16 C7 C6 116.80(18) . . ?
C16 C7 H7 107.5 . . ?
C16 C7 C8 103.87(15) . . ?
N1 C8 C7 103.16(15) . . ?
N1 C8 H8 108.2 . . ?
N1 C8 C9 109.75(14) . . ?
C7 C8 H8 108.2 . . ?
C9 C8 C7 118.78(16) . . ?
C9 C8 H8 108.2 . . ?
C10 C9 C8 127.18(19) . . ?
C10 C9 C11 118.90(18) . . ?
C11 C9 C8 113.86(18) . . ?
C2 C10 H10 113.7 . . ?
C9 C10 C2 132.53(18) . . ?
C9 C10 H10 113.7 . . ?
C9 C11 H11A 108.5 . . ?
C9 C11 H11B 108.5 . . ?
C9 C11 C12 115.13(18) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C11 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 C11 114.71(17) . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C12 113.41(19) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
O3 C14 N1 121.7(2) . . ?
O3 C14 C13 121.35(18) . . ?
N1 C14 C13 116.96(18) . . ?
C16 C15 N1 109.77(17) . . ?
C16 C15 C20 121.01(19) . . ?
C20 C15 N1 129.22(17) . . ?
C15 C16 C7 110.00(18) . . ?
C17 C16 C7 129.56(16) . . ?
C17 C16 C15 120.40(19) . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.40(18) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.9(2) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 H20 121.1 . . ?
C19 C20 C15 117.86(18) . . ?
C19 C20 H20 121.1 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C21 H21A 109.5 . . ?
C23 C21 H21B 109.5 . . ?
C23 C21 H21C 109.5 . . ?
C1 C22 H22 119.5 . . ?
C5 C22 C1 121.0(2) . . ?
C5 C22 H22 119.5 . . ?
O1 C23 O2 123.06(17) . . ?
O1 C23 C21 126.09(19) . . ?
O2 C23 C21 110.84(19) . . ?

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
O2 C6 C7 C8 153.52(17) . . . . ?
O2 C6 C7 C16 -85.82(19) . . . . ?
N1 C8 C9 C10 -93.8(2) . . . . ?
N1 C8 C9 C11 83.3(2) . . . . ?
N1 C15 C16 C7 2.1(2) . . . . ?
N1 C15 C16 C17 179.93(17) . . . . ?
N1 C15 C20 C19 179.24(18) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C10 C9 -32.1(3) . . . . ?
C1 C6 C7 C8 -83.8(2) . . . . ?
C1 C6 C7 C16 36.9(2) . . . . ?
C2 C1 C6 O2 -174.86(16) . . . . ?
C2 C1 C6 C7 65.9(2) . . . . ?
C2 C1 C22 C5 0.8(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C2 C10 C9 153.5(2) . . . . ?
C3 C4 C5 C22 0.2(3) . . . . ?
C4 C5 C22 C1 -0.4(3) . . . . ?
C6 O2 C23 O1 -2.4(3) . . . . ?
C6 O2 C23 C21 176.77(19) . . . . ?
C6 C1 C2 C3 177.72(18) . . . . ?
C6 C1 C2 C10 3.3(3) . . . . ?
C6 C1 C22 C5 -177.71(19) . . . . ?
C6 C7 C8 N1 145.82(17) . . . . ?
C6 C7 C8 C9 24.2(3) . . . . ?
C6 C7 C16 C15 -138.61(16) . . . . ?
C6 C7 C16 C17 43.8(3) . . . . ?
C7 C8 C9 C10 24.4(3) . . . . ?
C7 C8 C9 C11 -158.42(18) . . . . ?
C7 C16 C17 C18 178.24(19) . . . . ?
C8 N1 C14 O3 176.64(18) . . . . ?
C8 N1 C14 C13 -1.5(3) . . . . ?
C8 N1 C15 C16 10.5(2) . . . . ?
C8 N1 C15 C20 -169.12(19) . . . . ?
C8 C7 C16 C15 -13.1(2) . . . . ?
C8 C7 C16 C17 169.35(19) . . . . ?
C8 C9 C10 C2 -7.1(4) . . . . ?
C8 C9 C11 C12 -63.1(2) . . . . ?
C9 C11 C12 C13 58.5(3) . . . . ?
C10 C2 C3 C4 175.33(19) . . . . ?
C10 C9 C11 C12 114.3(2) . . . . ?
C11 C9 C10 C2 175.9(2) . . . . ?
C11 C12 C13 C14 -79.6(2) . . . . ?
C12 C13 C14 O3 -109.5(2) . . . . ?
C12 C13 C14 N1 68.6(2) . . . . ?
C14 N1 C8 C7 164.93(17) . . . . ?
C14 N1 C8 C9 -67.5(2) . . . . ?
C14 N1 C15 C16 -172.44(17) . . . . ?
C14 N1 C15 C20 8.0(3) . . . . ?
C15 N1 C8 C7 -17.93(19) . . . . ?
C15 N1 C8 C9 109.61(18) . . . . ?
C15 N1 C14 O3 0.0(3) . . . . ?
C15 N1 C14 C13 -178.18(18) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C7 C8 N1 18.07(19) . . . . ?
C16 C7 C8 C9 -103.6(2) . . . . ?
C16 C15 C20 C19 -0.3(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C15 0.6(3) . . . . ?
C20 C15 C16 C7 -178.28(17) . . . . ?
C20 C15 C16 C17 -0.4(3) . . . . ?
C22 C1 C2 C3 -0.9(3) . . . . ?
C22 C1 C2 C10 -175.27(18) . . . . ?
C22 C1 C6 O2 3.6(3) . . . . ?
C22 C1 C6 C7 -115.6(2) . . . . ?
C23 O2 C6 C1 84.0(2) . . . . ?
C23 O2 C6 C7 -152.17(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 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.772
####################################################################### 
# 
# 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_sdd27
_database_code_depnum_ccdc_archive 'CCDC 2157370'
loop_
_audit_author_name
_audit_author_address
'Rao Weidong'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2021-03-31
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 N O2'
_chemical_formula_sum            'C20 H13 N O2'
_chemical_formula_weight         299.31
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.30360(10)
_cell_length_b                   15.7882(3)
_cell_length_c                   20.5752(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2697.39(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4187
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6680
_cell_measurement_theta_min      4.2650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1133
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6939
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.730
_diffrn_reflns_theta_min         4.298
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  -8.00   1.00    1.00    --  -40.73  38.00-120.00   57
  2  ω    -94.00 -13.00   1.00    1.00    --  -40.73 -57.00-150.00   81
  3  ω    -94.00 -66.00   1.00    1.00    --  -40.73 125.00  60.00   28
  4  ω    -31.00  -2.00   1.00    1.00    --  -40.73 125.00  60.00   29
  5  ω    129.00 178.00   1.00    1.00    --  107.58  45.00 -90.00   49
  6  ω     76.00 163.00   1.00    1.00    --  107.58  77.00-180.00   87
  7  ω     31.00 108.00   1.00    1.00    --  107.58 -94.00-120.00   77
  8  ω     25.00  95.00   1.00    1.00    --  107.58 -94.00-180.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0122621000
_diffrn_orient_matrix_UB_12      -0.0644722000
_diffrn_orient_matrix_UB_13      -0.0559183000
_diffrn_orient_matrix_UB_21      0.0407399000
_diffrn_orient_matrix_UB_22      -0.0723315000
_diffrn_orient_matrix_UB_23      0.0474953000
_diffrn_orient_matrix_UB_31      -0.1806236000
_diffrn_orient_matrix_UB_32      -0.0119518000
_diffrn_orient_matrix_UB_33      0.0146771000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2369
_reflns_number_total             2673
_reflns_odcompleteness_completeness 99.89
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0029(8)
_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   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2673
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0706
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1181P)²+0.8314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1935
_refine_ls_wR_factor_ref         0.2020
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(C12B)=Sof(H12A)=Sof(H12B)=Sof(C13B)=Sof(H13C)=Sof(H13D)=1-FVAR(1)
 Sof(C12)=Sof(H12C)=Sof(H12D)=Sof(C13)=Sof(H13A)=Sof(H13B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C12(H12C,H12D), C12B(H12A,H12B), C13(H13A,H13B), C13B(H13C,H13D)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C17(H17), C18(H18), C19(H19),
 C20(H20)
;
_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 0.6963(2) 0.66419(10) 0.52082(10) 0.0684(6) Uani 1 1 d . . . . .
O2 O 0.3583(3) 0.39473(10) 0.73720(7) 0.0623(6) Uani 1 1 d . . . . .
N1 N 0.49071(19) 0.46507(10) 0.65705(8) 0.0345(4) Uani 1 1 d . . . . .
C1 C 0.8010(2) 0.44514(13) 0.47613(10) 0.0377(5) Uani 1 1 d . . . . .
C2 C 0.8932(2) 0.41020(15) 0.42496(10) 0.0436(5) Uani 1 1 d . . . . .
H2 H 0.903855 0.351646 0.422562 0.052 Uiso 1 1 calc R U . . .
C3 C 0.9671(3) 0.45866(18) 0.37905(11) 0.0530(6) Uani 1 1 d . . . . .
H3 H 1.027715 0.433457 0.346324 0.064 Uiso 1 1 calc R U . . .
C4 C 0.9510(3) 0.54596(18) 0.38165(11) 0.0559(6) Uani 1 1 d . . . . .
H4 H 1.000266 0.579665 0.350356 0.067 Uiso 1 1 calc R U . . .
C5 C 0.8627(2) 0.58256(15) 0.43028(10) 0.0443(5) Uani 1 1 d . . . . .
H5 H 0.853897 0.641261 0.431518 0.053 Uiso 1 1 calc R U . . .
C6 C 0.7849(2) 0.53455(12) 0.47833(10) 0.0358(5) Uani 1 1 d . . . . .
C7 C 0.6956(2) 0.58597(13) 0.52690(11) 0.0426(5) Uani 1 1 d . . . . .
C8 C 0.6071(2) 0.55108(12) 0.58191(10) 0.0354(5) Uani 1 1 d . . . . .
C9 C 0.5886(2) 0.46738(12) 0.60069(10) 0.0358(5) Uani 1 1 d . . . . .
C10 C 0.6464(3) 0.38959(13) 0.57412(16) 0.0634(9) Uani 1 1 d . . . . .
C11 C 0.7366(3) 0.38289(13) 0.52004(15) 0.0596(8) Uani 1 1 d . . . . .
H11 H 0.762227 0.327402 0.508937 0.071 Uiso 1 1 calc R U . . .
C12 C 0.6384(5) 0.3145(2) 0.6292(2) 0.0348(12) Uani 0.499(7) 1 d . . P A 1
H12C H 0.666469 0.260399 0.609966 0.042 Uiso 0.499(7) 1 calc R U P A 1
H12D H 0.713887 0.326383 0.664030 0.042 Uiso 0.499(7) 1 calc R U P A 1
C12B C 0.5591(5) 0.3087(2) 0.5917(2) 0.0368(12) Uani 0.501(7) 1 d . . P A 2
H12A H 0.451622 0.307477 0.573294 0.044 Uiso 0.501(7) 1 calc R U P A 2
H12B H 0.618221 0.259197 0.577105 0.044 Uiso 0.501(7) 1 calc R U P A 2
C13 C 0.4657(8) 0.3117(3) 0.6559(2) 0.0353(11) Uani 0.499(7) 1 d . . P A 1
H13A H 0.388468 0.305937 0.620808 0.042 Uiso 0.499(7) 1 calc R U P A 1
H13B H 0.452415 0.264536 0.685638 0.042 Uiso 0.499(7) 1 calc R U P A 1
C13B C 0.5537(8) 0.3133(3) 0.6649(2) 0.0392(12) Uani 0.501(7) 1 d . . P A 2
H13C H 0.662285 0.319946 0.681539 0.047 Uiso 0.501(7) 1 calc R U P A 2
H13D H 0.510425 0.260794 0.681941 0.047 Uiso 0.501(7) 1 calc R U P A 2
C14 C 0.4438(3) 0.39167(13) 0.68948(10) 0.0496(6) Uani 1 1 d . . . . .
C15 C 0.4448(2) 0.54838(12) 0.67289(9) 0.0352(5) Uani 1 1 d . . . . .
C16 C 0.5167(2) 0.60285(12) 0.62747(9) 0.0352(5) Uani 1 1 d . . . . .
C17 C 0.4872(3) 0.69015(12) 0.63250(10) 0.0417(5) Uani 1 1 d . . . . .
H17 H 0.533589 0.727983 0.603339 0.050 Uiso 1 1 calc R U . . .
C18 C 0.3879(3) 0.71863(13) 0.68166(11) 0.0508(6) Uani 1 1 d . . . . .
H18 H 0.368443 0.776401 0.685701 0.061 Uiso 1 1 calc R U . . .
C19 C 0.3159(3) 0.66273(15) 0.72541(10) 0.0499(6) Uani 1 1 d . . . . .
H19 H 0.248496 0.683886 0.757636 0.060 Uiso 1 1 calc R U . . .
C20 C 0.3430(3) 0.57664(14) 0.72178(9) 0.0430(5) Uani 1 1 d . . . . .
H20 H 0.295096 0.539192 0.750819 0.052 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 C7 1.241(3) . ?
O2 C14 1.213(3) . ?
N1 C9 1.417(3) . ?
N1 C14 1.393(2) . ?
N1 C15 1.408(2) . ?
C1 C2 1.414(3) . ?
C1 C6 1.419(3) . ?
C1 C11 1.438(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.403(3) . ?
C6 C7 1.486(3) . ?
C7 C8 1.457(3) . ?
C8 C9 1.385(3) . ?
C8 C16 1.453(3) . ?
C9 C10 1.427(3) . ?
C10 C11 1.346(3) . ?
C10 C12 1.641(4) . ?
C10 C12B 1.513(4) . ?
C11 H11 0.9300 . ?
C12 H12C 0.9700 . ?
C12 H12D 0.9700 . ?
C12 C13 1.537(7) . ?
C12B H12A 0.9700 . ?
C12B H12B 0.9700 . ?
C12B C13B 1.508(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.451(5) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C13B C14 1.618(5) . ?
C15 C16 1.403(3) . ?
C15 C20 1.388(3) . ?
C16 C17 1.404(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.395(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9300 . ?

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
C14 N1 C9 125.03(17) . . ?
C14 N1 C15 126.23(18) . . ?
C15 N1 C9 108.70(15) . . ?
C2 C1 C6 117.58(18) . . ?
C2 C1 C11 113.74(19) . . ?
C6 C1 C11 128.68(19) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 C1 122.8(2) . . ?
C3 C2 H2 118.6 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.3(2) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C7 127.75(17) . . ?
C5 C6 C1 118.14(19) . . ?
C5 C6 C7 114.11(18) . . ?
O1 C7 C6 118.25(18) . . ?
O1 C7 C8 117.19(19) . . ?
C8 C7 C6 124.56(18) . . ?
C9 C8 C7 129.28(18) . . ?
C9 C8 C16 107.42(17) . . ?
C16 C8 C7 123.29(17) . . ?
N1 C9 C10 118.96(17) . . ?
C8 C9 N1 108.46(17) . . ?
C8 C9 C10 132.6(2) . . ?
C9 C10 C12 110.1(3) . . ?
C9 C10 C12B 118.3(2) . . ?
C11 C10 C9 124.9(2) . . ?
C11 C10 C12 122.5(2) . . ?
C11 C10 C12B 113.5(2) . . ?
C1 C11 H11 113.9 . . ?
C10 C11 C1 132.3(2) . . ?
C10 C11 H11 113.9 . . ?
C10 C12 H12C 110.2 . . ?
C10 C12 H12D 110.2 . . ?
H12C C12 H12D 108.5 . . ?
C13 C12 C10 107.8(3) . . ?
C13 C12 H12C 110.2 . . ?
C13 C12 H12D 110.2 . . ?
C10 C12B H12A 111.3 . . ?
C10 C12B H12B 111.3 . . ?
H12A C12B H12B 109.2 . . ?
C13B C12B C10 102.2(3) . . ?
C13B C12B H12A 111.3 . . ?
C13B C12B H12B 111.3 . . ?
C12 C13 H13A 110.7 . . ?
C12 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 C12 105.2(4) . . ?
C14 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
C12B C13B H13C 109.3 . . ?
C12B C13B H13D 109.3 . . ?
C12B C13B C14 111.5(4) . . ?
H13C C13B H13D 108.0 . . ?
C14 C13B H13C 109.3 . . ?
C14 C13B H13D 109.3 . . ?
O2 C14 N1 121.2(2) . . ?
O2 C14 C13 119.6(3) . . ?
O2 C14 C13B 127.9(2) . . ?
N1 C14 C13 117.5(2) . . ?
N1 C14 C13B 109.2(2) . . ?
C16 C15 N1 107.66(17) . . ?
C20 C15 N1 129.28(18) . . ?
C20 C15 C16 123.02(18) . . ?
C15 C16 C8 107.74(17) . . ?
C15 C16 C17 118.58(18) . . ?
C17 C16 C8 133.65(19) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.56(19) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.5(2) . . ?
C19 C18 H18 119.2 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(2) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 H20 121.5 . . ?
C19 C20 C15 117.1(2) . . ?
C19 C20 H20 121.5 . . ?

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 C7 C8 C9 -178.9(2) . . . . ?
O1 C7 C8 C16 2.4(3) . . . . ?
N1 C9 C10 C11 178.2(2) . . . . ?
N1 C9 C10 C12 -19.8(3) . . . . ?
N1 C9 C10 C12B 20.4(4) . . . . ?
N1 C15 C16 C8 0.9(2) . . . . ?
N1 C15 C16 C17 179.20(17) . . . . ?
N1 C15 C20 C19 -178.52(19) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C6 C7 O1 179.5(2) . . . . ?
C1 C6 C7 C8 -0.1(3) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C1 C6 C7 -179.74(18) . . . . ?
C2 C1 C11 C10 179.0(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 179.8(2) . . . . ?
C5 C6 C7 O1 0.5(3) . . . . ?
C5 C6 C7 C8 -179.09(18) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C6 C1 C11 C10 -0.3(5) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C6 C7 C8 C16 -178.02(17) . . . . ?
C7 C8 C9 N1 -179.46(18) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C7 C8 C16 C15 178.74(17) . . . . ?
C7 C8 C16 C17 0.8(3) . . . . ?
C8 C9 C10 C11 -1.1(5) . . . . ?
C8 C9 C10 C12 160.9(2) . . . . ?
C8 C9 C10 C12B -158.9(3) . . . . ?
C8 C16 C17 C18 177.3(2) . . . . ?
C9 N1 C14 O2 -179.2(2) . . . . ?
C9 N1 C14 C13 -14.4(4) . . . . ?
C9 N1 C14 C13B 14.6(4) . . . . ?
C9 N1 C15 C16 -1.3(2) . . . . ?
C9 N1 C15 C20 176.28(18) . . . . ?
C9 C8 C16 C15 -0.2(2) . . . . ?
C9 C8 C16 C17 -178.1(2) . . . . ?
C9 C10 C11 C1 1.2(5) . . . . ?
C9 C10 C12 C13 53.6(4) . . . . ?
C9 C10 C12B C13B -51.6(5) . . . . ?
C10 C12 C13 C14 -66.0(4) . . . . ?
C10 C12B C13B C14 65.4(5) . . . . ?
C11 C1 C2 C3 -178.6(2) . . . . ?
C11 C1 C6 C5 178.5(2) . . . . ?
C11 C1 C6 C7 -0.5(3) . . . . ?
C11 C10 C12 C13 -143.9(3) . . . . ?
C11 C10 C12B C13B 148.2(4) . . . . ?
C12 C10 C11 C1 -158.6(3) . . . . ?
C12 C13 C14 O2 -147.2(3) . . . . ?
C12 C13 C14 N1 47.7(5) . . . . ?
C12B C10 C11 C1 160.0(3) . . . . ?
C12B C13B C14 O2 145.1(3) . . . . ?
C12B C13B C14 N1 -49.9(5) . . . . ?
C14 N1 C9 C8 179.04(18) . . . . ?
C14 N1 C9 C10 -0.4(3) . . . . ?
C14 N1 C15 C16 -179.13(19) . . . . ?
C14 N1 C15 C20 -1.5(3) . . . . ?
C15 N1 C9 C8 1.2(2) . . . . ?
C15 N1 C9 C10 -178.3(2) . . . . ?
C15 N1 C14 O2 -1.8(4) . . . . ?
C15 N1 C14 C13 163.1(3) . . . . ?
C15 N1 C14 C13B -167.9(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C8 C9 N1 -0.6(2) . . . . ?
C16 C8 C9 C10 178.7(2) . . . . ?
C16 C15 C20 C19 -1.3(3) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C17 C18 C19 C20 0.8(4) . . . . ?
C18 C19 C20 C15 0.1(3) . . . . ?
C20 C15 C16 C8 -176.84(17) . . . . ?
C20 C15 C16 C17 1.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.536
_oxdiff_exptl_absorpt_empirical_full_min 0.548
####################################################################### 
# 
# 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_105-2
_database_code_depnum_ccdc_archive 'CCDC 2156624'
loop_
_audit_author_name
_audit_author_address
'Rao Weidong'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-03-05 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2021-07-10
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H23 N O3'
_chemical_formula_sum            'C24 H23 N O3'
_chemical_formula_weight         373.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.8590(8)
_cell_length_b                   15.1688(8)
_cell_length_c                   22.7080(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3740.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3528
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.0040
_cell_measurement_theta_min      2.4810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.13
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9596
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.475
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  11.00   1.00    3.00    --  -11.27  57.00  90.00   47
  2  ω    -12.00  63.00   1.00    3.00    --   11.90  57.00 -30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0417461000
_diffrn_orient_matrix_UB_12      0.0020701000
_diffrn_orient_matrix_UB_13      -0.0239810000
_diffrn_orient_matrix_UB_21      0.0501514000
_diffrn_orient_matrix_UB_22      -0.0009558000
_diffrn_orient_matrix_UB_23      -0.0200091000
_diffrn_orient_matrix_UB_31      -0.0028927000
_diffrn_orient_matrix_UB_32      -0.0467014000
_diffrn_orient_matrix_UB_33      -0.0006572000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2718
_reflns_number_total             3286
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.026
_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)+(0.0418P)²+1.7315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1051
_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), C9(H9), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C17(H17), C18(H18), C19(H19),
 C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.07307(11) 0.63158(8) 0.70347(5) 0.0339(3) Uani 1 1 d . . . . .
O2 O 0.35043(13) 0.63433(9) 0.44639(6) 0.0429(4) Uani 1 1 d . . . . .
O3 O 0.24039(10) 0.60147(7) 0.64221(5) 0.0227(3) Uani 1 1 d . . . . .
N1 N 0.37473(12) 0.55814(9) 0.53114(6) 0.0236(3) Uani 1 1 d . . . . .
C1 C 0.16118(16) 0.41108(10) 0.66840(8) 0.0276(4) Uani 1 1 d . . . . .
C2 C 0.09208(18) 0.34683(12) 0.69794(9) 0.0379(5) Uani 1 1 d . . . . .
H2 H 0.038492 0.311381 0.676492 0.046 Uiso 1 1 calc R U . . .
C3 C 0.1014(2) 0.33476(13) 0.75783(10) 0.0440(5) Uani 1 1 d . . . . .
H3 H 0.054544 0.291475 0.776269 0.053 Uiso 1 1 calc R U . . .
C4 C 0.17971(19) 0.38655(12) 0.79050(9) 0.0393(5) Uani 1 1 d . . . . .
H4 H 0.187408 0.377932 0.830880 0.047 Uiso 1 1 calc R U . . .
C5 C 0.24699(17) 0.45173(12) 0.76238(8) 0.0315(4) Uani 1 1 d . . . . .
H5 H 0.299587 0.487093 0.784445 0.038 Uiso 1 1 calc R U . . .
C6 C 0.23791(15) 0.46560(10) 0.70216(7) 0.0241(4) Uani 1 1 d . . . . .
C7 C 0.31233(15) 0.53879(10) 0.67430(7) 0.0219(4) Uani 1 1 d . . . . .
H7 H 0.356437 0.570132 0.705588 0.026 Uiso 1 1 calc R U . . .
C8 C 0.40710(14) 0.50497(10) 0.62962(7) 0.0216(4) Uani 1 1 d . . . . .
H8 H 0.453467 0.455619 0.646478 0.026 Uiso 1 1 calc R U . . .
C9 C 0.35331(15) 0.47845(10) 0.56942(7) 0.0231(4) Uani 1 1 d . . . . .
H9 H 0.407529 0.432217 0.554028 0.028 Uiso 1 1 calc R U . . .
C10 C 0.22451(16) 0.44419(11) 0.56262(8) 0.0281(4) Uani 1 1 d . . . . .
C11 C 0.14837(16) 0.41568(11) 0.60441(8) 0.0300(4) Uani 1 1 d . . . . .
H11 H 0.073363 0.394912 0.590323 0.036 Uiso 1 1 calc R U . . .
C12 C 0.19251(18) 0.43431(13) 0.49842(9) 0.0396(5) Uani 1 1 d . . . . .
H12A H 0.108341 0.413547 0.494915 0.047 Uiso 1 1 calc R U . . .
H12B H 0.245999 0.390390 0.480815 0.047 Uiso 1 1 calc R U . . .
C13 C 0.20581(18) 0.51998(15) 0.46532(9) 0.0436(5) Uani 1 1 d . . . . .
H13A H 0.206519 0.506865 0.423517 0.052 Uiso 1 1 calc R U . . .
H13B H 0.133384 0.555572 0.473061 0.052 Uiso 1 1 calc R U . . .
C14 C 0.31792(17) 0.57455(12) 0.47923(8) 0.0303(4) Uani 1 1 d . . . . .
C15 C 0.49378(14) 0.57881(10) 0.61339(7) 0.0221(4) Uani 1 1 d . . . . .
C16 C 0.46681(15) 0.61077(10) 0.55738(7) 0.0231(4) Uani 1 1 d . . . . .
C17 C 0.52401(17) 0.68613(11) 0.53588(8) 0.0311(4) Uani 1 1 d . . . . .
H17 H 0.504461 0.708612 0.498944 0.037 Uiso 1 1 calc R U . . .
C18 C 0.61147(17) 0.72682(11) 0.57142(9) 0.0347(5) Uani 1 1 d . . . . .
H18 H 0.651648 0.776933 0.557731 0.042 Uiso 1 1 calc R U . . .
C19 C 0.63990(16) 0.69448(11) 0.62652(9) 0.0322(4) Uani 1 1 d . . . . .
H19 H 0.699315 0.722551 0.649285 0.039 Uiso 1 1 calc R U . . .
C20 C 0.58032(15) 0.62019(11) 0.64824(8) 0.0271(4) Uani 1 1 d . . . . .
H20 H 0.598470 0.598759 0.685618 0.032 Uiso 1 1 calc R U . . .
C21 C 0.17796(16) 0.66613(11) 0.67532(8) 0.0280(4) Uani 1 1 d . . . . .
H21 H 0.233274 0.694507 0.703667 0.034 Uiso 1 1 calc R U . . .
C22 C 0.12823(17) 0.73184(11) 0.63167(9) 0.0346(5) Uani 1 1 d . . . . .
H22A H 0.185922 0.742000 0.599769 0.042 Uiso 1 1 calc R U . . .
H22B H 0.108878 0.787576 0.650457 0.042 Uiso 1 1 calc R U . . .
C23 C 0.01292(17) 0.68581(13) 0.61006(9) 0.0385(5) Uani 1 1 d . . . . .
H23A H 0.028966 0.653867 0.573858 0.046 Uiso 1 1 calc R U . . .
H23B H -0.052734 0.727922 0.603158 0.046 Uiso 1 1 calc R U . . .
C24 C -0.02074(17) 0.62293(12) 0.65951(9) 0.0373(5) Uani 1 1 d . . . . .
H24A H -0.100578 0.638059 0.675785 0.045 Uiso 1 1 calc R U . . .
H24B H -0.023990 0.562821 0.645018 0.045 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 C21 1.407(2) . ?
O1 C24 1.432(2) . ?
O2 C14 1.226(2) . ?
O3 C7 1.4301(19) . ?
O3 C21 1.4096(19) . ?
N1 C9 1.507(2) . ?
N1 C14 1.353(2) . ?
N1 C16 1.411(2) . ?
C1 C2 1.401(2) . ?
C1 C6 1.402(2) . ?
C1 C11 1.461(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(2) . ?
C6 C7 1.512(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.533(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.540(2) . ?
C8 C15 1.509(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.500(2) . ?
C10 C11 1.331(2) . ?
C10 C12 1.506(3) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.508(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.506(3) . ?
C15 C16 1.392(2) . ?
C15 C20 1.380(2) . ?
C16 C17 1.390(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9800 . ?
C21 C22 1.506(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.515(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.518(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?

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
C21 O1 C24 107.05(13) . . ?
C21 O3 C7 116.96(12) . . ?
C14 N1 C9 125.41(14) . . ?
C14 N1 C16 125.91(15) . . ?
C16 N1 C9 108.63(13) . . ?
C2 C1 C11 117.28(17) . . ?
C6 C1 C2 117.83(17) . . ?
C6 C1 C11 124.89(15) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.77(19) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.17(18) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.04(19) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.68(18) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 121.46(15) . . ?
C5 C6 C1 119.46(16) . . ?
C5 C6 C7 119.08(16) . . ?
O3 C7 C6 114.17(13) . . ?
O3 C7 H7 108.3 . . ?
O3 C7 C8 104.59(12) . . ?
C6 C7 H7 108.3 . . ?
C6 C7 C8 112.95(13) . . ?
C8 C7 H7 108.3 . . ?
C7 C8 H8 110.0 . . ?
C7 C8 C9 114.84(13) . . ?
C9 C8 H8 110.0 . . ?
C15 C8 C7 109.39(12) . . ?
C15 C8 H8 110.0 . . ?
C15 C8 C9 102.34(13) . . ?
N1 C9 C8 104.12(12) . . ?
N1 C9 H9 106.0 . . ?
C8 C9 H9 106.0 . . ?
C10 C9 N1 111.25(14) . . ?
C10 C9 C8 122.37(14) . . ?
C10 C9 H9 106.0 . . ?
C9 C10 C12 110.44(15) . . ?
C11 C10 C9 128.21(16) . . ?
C11 C10 C12 120.96(16) . . ?
C1 C11 H11 114.1 . . ?
C10 C11 C1 131.71(17) . . ?
C10 C11 H11 114.1 . . ?
C10 C12 H12A 109.2 . . ?
C10 C12 H12B 109.2 . . ?
C10 C12 C13 111.99(16) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C12 C13 H13A 108.2 . . ?
C12 C13 H13B 108.2 . . ?
H13A C13 H13B 107.3 . . ?
C14 C13 C12 116.53(16) . . ?
C14 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
O2 C14 N1 122.31(17) . . ?
O2 C14 C13 120.79(17) . . ?
N1 C14 C13 116.75(16) . . ?
C16 C15 C8 110.51(14) . . ?
C20 C15 C8 128.51(15) . . ?
C20 C15 C16 120.59(15) . . ?
C15 C16 N1 109.74(14) . . ?
C17 C16 N1 129.32(16) . . ?
C17 C16 C15 120.89(16) . . ?
C16 C17 H17 121.1 . . ?
C16 C17 C18 117.80(17) . . ?
C18 C17 H17 121.1 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.44(17) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.42(17) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 118.84(17) . . ?
C15 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
O1 C21 O3 111.87(13) . . ?
O1 C21 H21 111.2 . . ?
O1 C21 C22 104.78(14) . . ?
O3 C21 H21 111.2 . . ?
O3 C21 C22 106.37(14) . . ?
C22 C21 H21 111.2 . . ?
C21 C22 H22A 111.4 . . ?
C21 C22 H22B 111.4 . . ?
C21 C22 C23 101.80(14) . . ?
H22A C22 H22B 109.3 . . ?
C23 C22 H22A 111.4 . . ?
C23 C22 H22B 111.4 . . ?
C22 C23 H23A 110.9 . . ?
C22 C23 H23B 110.9 . . ?
C22 C23 C24 104.42(15) . . ?
H23A C23 H23B 108.9 . . ?
C24 C23 H23A 110.9 . . ?
C24 C23 H23B 110.9 . . ?
O1 C24 C23 106.66(15) . . ?
O1 C24 H24A 110.4 . . ?
O1 C24 H24B 110.4 . . ?
C23 C24 H24A 110.4 . . ?
C23 C24 H24B 110.4 . . ?
H24A C24 H24B 108.6 . . ?

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 C21 C22 C23 -38.04(17) . . . . ?
O3 C7 C8 C9 -47.65(16) . . . . ?
O3 C7 C8 C15 66.72(15) . . . . ?
O3 C21 C22 C23 80.58(16) . . . . ?
N1 C9 C10 C11 -137.93(18) . . . . ?
N1 C9 C10 C12 49.31(18) . . . . ?
N1 C16 C17 C18 178.93(15) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C1 C6 C7 O3 56.9(2) . . . . ?
C1 C6 C7 C8 -62.4(2) . . . . ?
C2 C1 C6 C5 2.9(2) . . . . ?
C2 C1 C6 C7 -177.80(15) . . . . ?
C2 C1 C11 C10 -153.78(19) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C5 C6 C7 179.04(16) . . . . ?
C5 C6 C7 O3 -123.75(16) . . . . ?
C5 C6 C7 C8 116.91(17) . . . . ?
C6 C1 C2 C3 -2.2(3) . . . . ?
C6 C1 C11 C10 25.7(3) . . . . ?
C6 C7 C8 C9 77.08(17) . . . . ?
C6 C7 C8 C15 -168.55(13) . . . . ?
C7 O3 C21 O1 -75.60(17) . . . . ?
C7 O3 C21 C22 170.54(13) . . . . ?
C7 C8 C9 N1 97.46(15) . . . . ?
C7 C8 C9 C10 -29.5(2) . . . . ?
C7 C8 C15 C16 -105.11(15) . . . . ?
C7 C8 C15 C20 67.6(2) . . . . ?
C8 C9 C10 C11 -14.1(3) . . . . ?
C8 C9 C10 C12 173.12(14) . . . . ?
C8 C15 C16 N1 -5.79(18) . . . . ?
C8 C15 C16 C17 171.79(14) . . . . ?
C8 C15 C20 C19 -171.92(15) . . . . ?
C9 N1 C14 O2 -170.27(15) . . . . ?
C9 N1 C14 C13 14.2(2) . . . . ?
C9 N1 C16 C15 -8.67(17) . . . . ?
C9 N1 C16 C17 174.01(16) . . . . ?
C9 C8 C15 C16 17.09(17) . . . . ?
C9 C8 C15 C20 -170.19(16) . . . . ?
C9 C10 C11 C1 2.5(3) . . . . ?
C9 C10 C12 C13 -57.5(2) . . . . ?
C10 C12 C13 C14 42.5(2) . . . . ?
C11 C1 C2 C3 177.33(17) . . . . ?
C11 C1 C6 C5 -176.63(16) . . . . ?
C11 C1 C6 C7 2.7(3) . . . . ?
C11 C10 C12 C13 129.17(19) . . . . ?
C12 C10 C11 C1 174.60(17) . . . . ?
C12 C13 C14 O2 164.16(18) . . . . ?
C12 C13 C14 N1 -20.2(3) . . . . ?
C14 N1 C9 C8 -163.17(15) . . . . ?
C14 N1 C9 C10 -29.5(2) . . . . ?
C14 N1 C16 C15 173.46(15) . . . . ?
C14 N1 C16 C17 -3.9(3) . . . . ?
C15 C8 C9 N1 -20.94(15) . . . . ?
C15 C8 C9 C10 -147.95(15) . . . . ?
C15 C16 C17 C18 1.9(2) . . . . ?
C16 N1 C9 C8 18.96(16) . . . . ?
C16 N1 C9 C10 152.60(13) . . . . ?
C16 N1 C14 O2 7.2(3) . . . . ?
C16 N1 C14 C13 -168.33(16) . . . . ?
C16 C15 C20 C19 0.2(2) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C15 0.9(2) . . . . ?
C20 C15 C16 N1 -179.18(14) . . . . ?
C20 C15 C16 C17 -1.6(2) . . . . ?
C21 O1 C24 C23 -22.05(18) . . . . ?
C21 O3 C7 C6 79.01(17) . . . . ?
C21 O3 C7 C8 -157.04(12) . . . . ?
C21 C22 C23 C24 23.81(18) . . . . ?
C22 C23 C24 O1 -2.44(19) . . . . ?
C24 O1 C21 O3 -76.79(16) . . . . ?
C24 O1 C21 C22 38.05(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.409
_oxdiff_exptl_absorpt_empirical_full_min 0.602
####################################################################### 
# 
# 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_493
_database_code_depnum_ccdc_archive 'CCDC 2189548'
loop_
_audit_author_name
_audit_author_address
'Rao Weidong'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2022-05-19
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H31 N O4'
_chemical_formula_sum            'C32 H31 N O4'
_chemical_formula_weight         493.58
_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      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                   7.7872(2)
_cell_length_b                   22.5373(5)
_cell_length_c                   14.1266(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2479.25(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7010
_cell_measurement_temperature    170.02(18)
_cell_measurement_theta_max      73.7000
_cell_measurement_theta_min      3.1230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9526
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.977
_diffrn_reflns_theta_min         3.693
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.02(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  34.00   1.00    1.00    --  -40.73  38.00-180.00   99
  2  ω   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00-150.00  109
  3  ω     76.00 178.00   1.00    1.00    --  108.20  77.00  60.00  102
  4  ω     81.00 176.00   1.00    1.00    --  108.20  77.00  90.00   95
  5  ω    130.00 156.00   1.00    1.00    --  108.20 125.00-120.00   26
  6  ω     31.00  92.00   1.00    1.00    --  108.20 -94.00 -60.00   61
  7  ω     27.00  97.00   1.00    1.00    --  108.20 -94.00-120.00   70
  8  ω     32.00 108.00   1.00    1.00    --  108.20 -94.00   0.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0897471000
_diffrn_orient_matrix_UB_12      0.0603435000
_diffrn_orient_matrix_UB_13      0.0132086000
_diffrn_orient_matrix_UB_21      0.1462874000
_diffrn_orient_matrix_UB_22      -0.0202250000
_diffrn_orient_matrix_UB_23      -0.0660075000
_diffrn_orient_matrix_UB_31      -0.0984329000
_diffrn_orient_matrix_UB_32      0.0249325000
_diffrn_orient_matrix_UB_33      -0.0858008000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                4654
_reflns_number_total             4916
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 
;
 Flack x determined using 1783 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4916
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.102
_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)+(0.0590P)²+0.7064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1222
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C23(H23), C24(H24), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C16(H16A,H16B),
 C17(H17A,H17B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C28(H28), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.1763(3) 0.32266(12) 0.98285(18) 0.0471(6) Uani 1 1 d . . . . .
O2 O 0.2918(3) 0.35826(11) 0.32648(17) 0.0432(5) Uani 1 1 d . . . . .
O3 O 0.7224(3) 0.35092(8) 0.24760(14) 0.0305(4) Uani 1 1 d . . . . .
O4 O 0.5926(4) 0.48359(13) 0.00741(17) 0.0584(7) Uani 1 1 d . . . . .
N1 N 0.6468(3) 0.47074(11) 0.16413(17) 0.0330(5) Uani 1 1 d . . . . .
C1 C 0.5583(4) 0.30586(13) 0.5757(2) 0.0305(6) Uani 1 1 d . . . . .
C2 C 0.4677(4) 0.31727(13) 0.4936(2) 0.0314(6) Uani 1 1 d . . . . .
H2 H 0.350976 0.308604 0.491318 0.038 Uiso 1 1 calc R U . . .
C3 C 0.5471(4) 0.34140(12) 0.4145(2) 0.0284(6) Uani 1 1 d . . . . .
C4 C 0.7241(4) 0.35330(12) 0.4167(2) 0.0283(6) Uani 1 1 d . . . . .
C5 C 0.8147(4) 0.34264(12) 0.4995(2) 0.0283(6) Uani 1 1 d . . . . .
H5 H 0.931565 0.351011 0.501339 0.034 Uiso 1 1 calc R U . . .
C6 C 0.7350(3) 0.31963(12) 0.5802(2) 0.0264(5) Uani 1 1 d . . . . .
C7 C 0.8295(3) 0.30827(12) 0.6724(2) 0.0282(6) Uani 1 1 d . . . . .
H7 H 0.854702 0.265682 0.674230 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7097(3) 0.32114(12) 0.7570(2) 0.0270(5) Uani 1 1 d . . . . .
H8 H 0.671113 0.362479 0.754088 0.032 Uiso 1 1 calc R U . . .
C9 C 0.5531(4) 0.27971(15) 0.7508(2) 0.0404(7) Uani 1 1 d . . . . .
H9A H 0.590476 0.239221 0.761645 0.049 Uiso 1 1 calc R U . . .
H9B H 0.472793 0.290036 0.800627 0.049 Uiso 1 1 calc R U . . .
C10 C 0.4643(6) 0.2827(3) 0.6595(3) 0.0766(17) Uani 1 1 d . . . . .
H10A H 0.362610 0.306959 0.668010 0.092 Uiso 1 1 calc R U . . .
H10B H 0.425182 0.242925 0.644239 0.092 Uiso 1 1 calc R U . . .
C11 C 0.8060(3) 0.31101(12) 0.8490(2) 0.0281(6) Uani 1 1 d . . . . .
H11 H 0.840114 0.269156 0.848359 0.034 Uiso 1 1 calc R U . . .
C12 C 0.7182(4) 0.32089(16) 0.9445(2) 0.0386(7) Uani 1 1 d . . . . .
H12A H 0.634284 0.290122 0.957362 0.046 Uiso 1 1 calc R U . . .
H12B H 0.662170 0.359302 0.946926 0.046 Uiso 1 1 calc R U . . .
C13 C 0.8699(4) 0.31774(18) 1.0145(2) 0.0447(8) Uani 1 1 d . . . . .
H13A H 0.858496 0.347840 1.063139 0.054 Uiso 1 1 calc R U . . .
H13B H 0.874781 0.279080 1.044528 0.054 Uiso 1 1 calc R U . . .
C14 C 1.0301(4) 0.32855(13) 0.9554(2) 0.0348(7) Uani 1 1 d . . . . .
C15 C 0.9746(4) 0.34659(12) 0.8567(2) 0.0299(6) Uani 1 1 d . . . . .
C16 C 1.0918(4) 0.32979(15) 0.7762(2) 0.0359(7) Uani 1 1 d . . . . .
H16A H 1.122859 0.288257 0.781694 0.043 Uiso 1 1 calc R U . . .
H16B H 1.196209 0.353142 0.779681 0.043 Uiso 1 1 calc R U . . .
C17 C 1.0034(4) 0.34055(15) 0.6804(2) 0.0365(7) Uani 1 1 d . . . . .
H17A H 1.078432 0.327033 0.630040 0.044 Uiso 1 1 calc R U . . .
H17B H 0.985336 0.382809 0.672064 0.044 Uiso 1 1 calc R U . . .
C18 C 0.4485(4) 0.35774(12) 0.3294(2) 0.0312(6) Uani 1 1 d . . . . .
C19 C 0.5542(3) 0.37761(11) 0.2436(2) 0.0288(6) Uani 1 1 d . . . . .
C20 C 0.4668(4) 0.36290(13) 0.1499(2) 0.0365(7) Uani 1 1 d . . . . .
H20A H 0.368380 0.337634 0.161923 0.044 Uiso 1 1 calc R U . . .
H20B H 0.546304 0.341005 0.110212 0.044 Uiso 1 1 calc R U . . .
C21 C 0.4073(5) 0.41875(15) 0.0969(2) 0.0411(7) Uani 1 1 d . . . . .
H21A H 0.361665 0.407588 0.035544 0.049 Uiso 1 1 calc R U . . .
H21B H 0.316250 0.437921 0.132420 0.049 Uiso 1 1 calc R U . . .
C22 C 0.5534(5) 0.46128(14) 0.0838(2) 0.0402(7) Uani 1 1 d . . . . .
C23 C 0.5950(4) 0.44436(12) 0.2555(2) 0.0284(6) Uani 1 1 d . . . . .
H23 H 0.499729 0.466041 0.284788 0.034 Uiso 1 1 calc R U . . .
C24 C 0.8024(4) 0.37878(12) 0.3283(2) 0.0286(6) Uani 1 1 d . . . . .
H24 H 0.926946 0.372473 0.327501 0.034 Uiso 1 1 calc R U . . .
C25 C 0.7589(4) 0.44587(12) 0.3173(2) 0.0285(6) Uani 1 1 d . . . . .
H25 H 0.737999 0.464845 0.378668 0.034 Uiso 1 1 calc R U . . .
C26 C 0.8841(4) 0.48057(12) 0.2582(2) 0.0303(6) Uani 1 1 d . . . . .
C27 C 0.8153(4) 0.49400(12) 0.1703(2) 0.0316(6) Uani 1 1 d . . . . .
C28 C 0.9077(5) 0.52532(14) 0.1025(2) 0.0380(7) Uani 1 1 d . . . . .
H28 H 0.860584 0.533987 0.043611 0.046 Uiso 1 1 calc R U . . .
C29 C 1.0725(5) 0.54313(14) 0.1260(2) 0.0410(7) Uani 1 1 d . . . . .
H29 H 1.137690 0.563748 0.081764 0.049 Uiso 1 1 calc R U . . .
C30 C 1.1422(5) 0.53090(14) 0.2141(2) 0.0403(7) Uani 1 1 d . . . . .
H30 H 1.252650 0.543787 0.228328 0.048 Uiso 1 1 calc R U . . .
C31 C 1.0485(4) 0.49950(14) 0.2814(2) 0.0376(7) Uani 1 1 d . . . . .
H31 H 1.094989 0.491373 0.340638 0.045 Uiso 1 1 calc R U . . .
C32 C 0.9452(5) 0.41389(14) 0.8620(3) 0.0438(8) Uani 1 1 d . . . . .
H32A H 0.893225 0.427347 0.804286 0.066 Uiso 1 1 calc R U . . .
H32B H 1.053288 0.433627 0.870841 0.066 Uiso 1 1 calc R U . . .
H32C H 0.870758 0.422766 0.914324 0.066 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 C14 1.210(4) . ?
O2 C18 1.221(4) . ?
O3 C19 1.443(3) . ?
O3 C24 1.443(3) . ?
O4 C22 1.229(4) . ?
N1 C22 1.364(4) . ?
N1 C23 1.477(4) . ?
N1 C27 1.416(4) . ?
C1 C2 1.381(4) . ?
C1 C6 1.412(4) . ?
C1 C10 1.488(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(4) . ?
C3 C4 1.404(4) . ?
C3 C18 1.474(4) . ?
C4 C5 1.386(4) . ?
C4 C24 1.504(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.398(4) . ?
C6 C7 1.518(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.544(4) . ?
C7 C17 1.541(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.539(4) . ?
C8 C11 1.518(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.465(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9800 . ?
C11 C12 1.528(4) . ?
C11 C15 1.542(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.542(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.521(5) . ?
C14 C15 1.514(4) . ?
C15 C16 1.506(4) . ?
C15 C32 1.536(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.538(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.532(4) . ?
C19 C20 1.525(4) . ?
C19 C23 1.547(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.536(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.499(5) . ?
C23 H23 0.9800 . ?
C23 C25 1.547(4) . ?
C24 H24 0.9800 . ?
C24 C25 1.557(4) . ?
C25 H25 0.9800 . ?
C25 C26 1.503(4) . ?
C26 C27 1.386(4) . ?
C26 C31 1.389(4) . ?
C27 C28 1.390(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.385(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.384(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.392(4) . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 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 O3 C24 104.0(2) . . ?
C22 N1 C23 121.2(2) . . ?
C22 N1 C27 127.1(3) . . ?
C27 N1 C23 110.4(2) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 C10 118.8(3) . . ?
C6 C1 C10 121.4(3) . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 C18 121.5(3) . . ?
C4 C3 C18 118.8(3) . . ?
C3 C4 C24 116.9(3) . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 C24 124.1(2) . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C7 118.3(2) . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 C7 123.2(2) . . ?
C6 C7 H7 106.5 . . ?
C6 C7 C8 109.9(2) . . ?
C6 C7 C17 114.2(2) . . ?
C8 C7 H7 106.5 . . ?
C17 C7 H7 106.5 . . ?
C17 C7 C8 112.7(2) . . ?
C7 C8 H8 109.3 . . ?
C9 C8 C7 108.7(2) . . ?
C9 C8 H8 109.3 . . ?
C11 C8 C7 109.7(2) . . ?
C11 C8 H8 109.3 . . ?
C11 C8 C9 110.5(2) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C8 113.4(3) . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C1 C10 H10A 107.6 . . ?
C1 C10 H10B 107.6 . . ?
C9 C10 C1 119.0(3) . . ?
C9 C10 H10A 107.6 . . ?
C9 C10 H10B 107.6 . . ?
H10A C10 H10B 107.0 . . ?
C8 C11 H11 105.7 . . ?
C8 C11 C12 120.8(2) . . ?
C8 C11 C15 113.7(2) . . ?
C12 C11 H11 105.7 . . ?
C12 C11 C15 104.1(2) . . ?
C15 C11 H11 105.7 . . ?
C11 C12 H12A 111.3 . . ?
C11 C12 H12B 111.3 . . ?
C11 C12 C13 102.5(3) . . ?
H12A C12 H12B 109.2 . . ?
C13 C12 H12A 111.3 . . ?
C13 C12 H12B 111.3 . . ?
C12 C13 H13A 110.6 . . ?
C12 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 C12 105.6(2) . . ?
C14 C13 H13A 110.6 . . ?
C14 C13 H13B 110.6 . . ?
O1 C14 C13 125.3(3) . . ?
O1 C14 C15 126.4(3) . . ?
C15 C14 C13 108.3(3) . . ?
C14 C15 C11 99.7(2) . . ?
C14 C15 C32 105.2(2) . . ?
C16 C15 C11 109.4(2) . . ?
C16 C15 C14 117.0(2) . . ?
C16 C15 C32 112.0(3) . . ?
C32 C15 C11 113.0(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 C17 110.7(2) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C7 C17 H17A 109.1 . . ?
C7 C17 H17B 109.1 . . ?
C16 C17 C7 112.5(2) . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
O2 C18 C3 123.5(3) . . ?
O2 C18 C19 120.5(3) . . ?
C3 C18 C19 116.0(2) . . ?
O3 C19 C18 109.6(2) . . ?
O3 C19 C20 110.4(2) . . ?
O3 C19 C23 102.4(2) . . ?
C18 C19 C23 108.0(2) . . ?
C20 C19 C18 112.6(2) . . ?
C20 C19 C23 113.4(2) . . ?
C19 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 . . ?
C19 C20 C21 112.3(2) . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C22 C21 C20 110.8(3) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
O4 C22 N1 122.3(3) . . ?
O4 C22 C21 123.9(3) . . ?
N1 C22 C21 113.7(3) . . ?
N1 C23 C19 110.7(2) . . ?
N1 C23 H23 112.0 . . ?
N1 C23 C25 105.0(2) . . ?
C19 C23 H23 112.0 . . ?
C19 C23 C25 104.6(2) . . ?
C25 C23 H23 112.0 . . ?
O3 C24 C4 108.3(2) . . ?
O3 C24 H24 110.8 . . ?
O3 C24 C25 104.5(2) . . ?
C4 C24 H24 110.8 . . ?
C4 C24 C25 111.4(2) . . ?
C25 C24 H24 110.8 . . ?
C23 C25 C24 102.4(2) . . ?
C23 C25 H25 111.8 . . ?
C24 C25 H25 111.8 . . ?
C26 C25 C23 103.5(2) . . ?
C26 C25 C24 114.8(2) . . ?
C26 C25 H25 111.8 . . ?
C27 C26 C25 111.2(2) . . ?
C27 C26 C31 120.0(3) . . ?
C31 C26 C25 128.8(3) . . ?
C26 C27 N1 109.4(3) . . ?
C26 C27 C28 121.9(3) . . ?
C28 C27 N1 128.7(3) . . ?
C27 C28 H28 121.3 . . ?
C29 C28 C27 117.5(3) . . ?
C29 C28 H28 121.3 . . ?
C28 C29 H29 119.3 . . ?
C30 C29 C28 121.4(3) . . ?
C30 C29 H29 119.3 . . ?
C29 C30 H30 119.7 . . ?
C29 C30 C31 120.6(3) . . ?
C31 C30 H30 119.7 . . ?
C26 C31 C30 118.6(3) . . ?
C26 C31 H31 120.7 . . ?
C30 C31 H31 120.7 . . ?
C15 C32 H32A 109.5 . . ?
C15 C32 H32B 109.5 . . ?
C15 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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 C14 C15 C11 147.1(3) . . . . ?
O1 C14 C15 C16 29.4(5) . . . . ?
O1 C14 C15 C32 -95.7(4) . . . . ?
O2 C18 C19 O3 -156.2(3) . . . . ?
O2 C18 C19 C20 -33.0(4) . . . . ?
O2 C18 C19 C23 93.0(3) . . . . ?
O3 C19 C20 C21 -125.4(3) . . . . ?
O3 C19 C23 N1 82.3(3) . . . . ?
O3 C19 C23 C25 -30.3(3) . . . . ?
O3 C24 C25 C23 23.8(3) . . . . ?
O3 C24 C25 C26 -87.6(3) . . . . ?
N1 C23 C25 C24 -112.6(2) . . . . ?
N1 C23 C25 C26 7.0(3) . . . . ?
N1 C27 C28 C29 -179.7(3) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C1 C2 C3 C18 -175.4(3) . . . . ?
C1 C6 C7 C8 -35.6(3) . . . . ?
C1 C6 C7 C17 -163.2(3) . . . . ?
C2 C1 C6 C5 -2.3(4) . . . . ?
C2 C1 C6 C7 178.2(3) . . . . ?
C2 C1 C10 C9 -170.1(4) . . . . ?
C2 C3 C4 C5 -2.4(4) . . . . ?
C2 C3 C4 C24 179.3(2) . . . . ?
C2 C3 C18 O2 9.3(4) . . . . ?
C2 C3 C18 C19 -173.7(2) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C3 C4 C24 O3 -38.0(3) . . . . ?
C3 C4 C24 C25 76.4(3) . . . . ?
C3 C18 C19 O3 26.7(3) . . . . ?
C3 C18 C19 C20 149.9(2) . . . . ?
C3 C18 C19 C23 -84.1(3) . . . . ?
C4 C3 C18 O2 -167.6(3) . . . . ?
C4 C3 C18 C19 9.4(4) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
C4 C5 C6 C7 -179.1(3) . . . . ?
C4 C24 C25 C23 -93.0(3) . . . . ?
C4 C24 C25 C26 155.6(2) . . . . ?
C5 C4 C24 O3 143.8(3) . . . . ?
C5 C4 C24 C25 -101.9(3) . . . . ?
C5 C6 C7 C8 144.9(3) . . . . ?
C5 C6 C7 C17 17.3(4) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C6 C1 C10 C9 6.1(7) . . . . ?
C6 C7 C8 C9 60.4(3) . . . . ?
C6 C7 C8 C11 -178.8(2) . . . . ?
C6 C7 C17 C16 177.8(2) . . . . ?
C7 C8 C9 C10 -53.6(4) . . . . ?
C7 C8 C11 C12 179.6(3) . . . . ?
C7 C8 C11 C15 54.7(3) . . . . ?
C8 C7 C17 C16 51.6(3) . . . . ?
C8 C9 C10 C1 20.8(6) . . . . ?
C8 C11 C12 C13 -169.2(3) . . . . ?
C8 C11 C15 C14 177.6(2) . . . . ?
C8 C11 C15 C16 -59.1(3) . . . . ?
C8 C11 C15 C32 66.4(3) . . . . ?
C9 C8 C11 C12 -60.6(4) . . . . ?
C9 C8 C11 C15 174.5(2) . . . . ?
C10 C1 C2 C3 177.1(3) . . . . ?
C10 C1 C6 C5 -178.5(4) . . . . ?
C10 C1 C6 C7 2.0(5) . . . . ?
C11 C8 C9 C10 -174.0(3) . . . . ?
C11 C12 C13 C14 19.5(3) . . . . ?
C11 C15 C16 C17 57.2(3) . . . . ?
C12 C11 C15 C14 44.2(3) . . . . ?
C12 C11 C15 C16 167.4(2) . . . . ?
C12 C11 C15 C32 -67.0(3) . . . . ?
C12 C13 C14 O1 -170.8(3) . . . . ?
C12 C13 C14 C15 8.1(4) . . . . ?
C13 C14 C15 C11 -31.8(3) . . . . ?
C13 C14 C15 C16 -149.5(3) . . . . ?
C13 C14 C15 C32 85.4(3) . . . . ?
C14 C15 C16 C17 169.5(3) . . . . ?
C15 C11 C12 C13 -40.0(3) . . . . ?
C15 C16 C17 C7 -55.1(3) . . . . ?
C17 C7 C8 C9 -171.1(2) . . . . ?
C17 C7 C8 C11 -50.3(3) . . . . ?
C18 C3 C4 C5 174.6(2) . . . . ?
C18 C3 C4 C24 -3.7(4) . . . . ?
C18 C19 C20 C21 111.8(3) . . . . ?
C18 C19 C23 N1 -162.1(2) . . . . ?
C18 C19 C23 C25 85.3(3) . . . . ?
C19 O3 C24 C4 74.1(2) . . . . ?
C19 O3 C24 C25 -44.8(3) . . . . ?
C19 C20 C21 C22 54.3(4) . . . . ?
C19 C23 C25 C24 4.0(3) . . . . ?
C19 C23 C25 C26 123.6(2) . . . . ?
C20 C19 C23 N1 -36.6(3) . . . . ?
C20 C19 C23 C25 -149.2(2) . . . . ?
C20 C21 C22 O4 129.2(4) . . . . ?
C20 C21 C22 N1 -47.3(4) . . . . ?
C22 N1 C23 C19 48.1(4) . . . . ?
C22 N1 C23 C25 160.5(3) . . . . ?
C22 N1 C27 C26 -162.2(3) . . . . ?
C22 N1 C27 C28 17.2(5) . . . . ?
C23 N1 C22 O4 178.8(3) . . . . ?
C23 N1 C22 C21 -4.7(4) . . . . ?
C23 N1 C27 C26 4.6(3) . . . . ?
C23 N1 C27 C28 -175.9(3) . . . . ?
C23 C19 C20 C21 -11.2(4) . . . . ?
C23 C25 C26 C27 -4.7(3) . . . . ?
C23 C25 C26 C31 174.8(3) . . . . ?
C24 O3 C19 C18 -67.7(2) . . . . ?
C24 O3 C19 C20 167.8(2) . . . . ?
C24 O3 C19 C23 46.7(3) . . . . ?
C24 C4 C5 C6 179.1(3) . . . . ?
C24 C25 C26 C27 106.0(3) . . . . ?
C24 C25 C26 C31 -74.5(4) . . . . ?
C25 C26 C27 N1 0.3(3) . . . . ?
C25 C26 C27 C28 -179.2(3) . . . . ?
C25 C26 C31 C30 179.4(3) . . . . ?
C26 C27 C28 C29 -0.3(4) . . . . ?
C27 N1 C22 O4 -15.6(5) . . . . ?
C27 N1 C22 C21 160.9(3) . . . . ?
C27 N1 C23 C19 -119.7(2) . . . . ?
C27 N1 C23 C25 -7.3(3) . . . . ?
C27 C26 C31 C30 -1.2(4) . . . . ?
C27 C28 C29 C30 -0.8(5) . . . . ?
C28 C29 C30 C31 0.8(5) . . . . ?
C29 C30 C31 C26 0.2(5) . . . . ?
C31 C26 C27 N1 -179.2(3) . . . . ?
C31 C26 C27 C28 1.3(4) . . . . ?
C32 C15 C16 C17 -68.9(3) . . . . ?

_olex2_date_sample_data_collection 2022-05-19
_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 1.754
_oxdiff_exptl_absorpt_empirical_full_min 0.505
####################################################################### 
# 
# 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_568
_database_code_depnum_ccdc_archive 'CCDC 2189549'
loop_
_audit_author_name
_audit_author_address
'Rao Weidong'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2022-07-02
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C21 H19 N O3)'
_chemical_formula_sum            'C42 H38 N2 O6'
_chemical_formula_weight         666.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.9118(8)
_cell_length_b                   11.4750(3)
_cell_length_c                   13.8228(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.290(4)
_cell_angle_gamma                90
_cell_volume                     3300.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13425
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      71.2080
_cell_measurement_theta_min      3.3180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
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    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17657
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.515
_diffrn_reflns_theta_min         4.250
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     96.00 132.00   0.50    0.50    --   42.30  77.00 -30.00   72
  2  ω     13.00 130.00   0.50    0.50    --   42.30  57.00-180.00  234
  3  ω     39.00  71.00   0.50    0.50    --   42.30 -82.00-180.00   64
  4  ω     83.00 113.00   0.50    0.50    --   42.30  77.00 150.00   60
  5  ω     80.00 131.00   0.50    0.50    --   42.30  77.00   0.00  102
  6  ω     85.00 124.00   0.50    0.50    --   42.30  77.00 -60.00   78
  7  ω     70.00 181.00   0.50    0.50    --  101.60  63.00   0.00  222
  8  ω    107.00 191.00   0.50    0.50    --  101.60  82.00 -60.00  168
  9  ω     12.00 145.00   0.50    0.50    --  101.60 -82.00   0.00  266
 10  ω     16.00 117.00   0.50    0.50    --  101.60 -82.00 120.00  202
 11  ω    110.00 141.00   0.50    0.50    --  101.60 -77.00-180.00   62
 12  ω     83.00 140.00   0.50    0.50    --  101.60 -77.00-150.00  114
 13  ω     22.00  53.00   0.50    0.50    --  101.60 -77.00-180.00   62
 14  ω     79.00 174.00   0.50    0.50    --  101.60  77.00  30.00  190
 15  ω    -13.00  53.00   0.50    0.50    --   42.30 -82.00  90.00  132
 16  ω     80.00 105.00   0.50    0.50    --   42.30  77.00 -90.00   50
 17  ω    -15.00  26.00   0.50    0.50    --   42.30 -57.00-180.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0286512000
_diffrn_orient_matrix_UB_12      -0.1003590000
_diffrn_orient_matrix_UB_13      -0.0743479000
_diffrn_orient_matrix_UB_21      0.0001564000
_diffrn_orient_matrix_UB_22      0.0785138000
_diffrn_orient_matrix_UB_23      -0.0903863000
_diffrn_orient_matrix_UB_31      0.0682828000
_diffrn_orient_matrix_UB_32      -0.0422717000
_diffrn_orient_matrix_UB_33      0.0089523000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5794
_reflns_number_total             6181
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.00152(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         6181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0855
_refine_ls_restrained_S_all      1.183
_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)+(0.0457P)²+12.5529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2178
_refine_ls_wR_factor_ref         0.2192
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C40(H40), C7(H7), C38(H38), C9(H9), C39(H39), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C29(H29A,H29B), C15(H15A,H15B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C36(H36), C19(H19), C20(H20), C18(H18), C2(H2), C33(H33), C42(H42),
 C5(H5), C34(H34), C45(H45), C35(H35), C43(H43), C3(H3), C4(H4), C44(H44)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C50(H50A,H50B,H50C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.32108(12) 0.9513(2) 0.55645(19) 0.0228(6) Uani 1 1 d . . . . .
O4 O 0.17969(12) 0.4018(2) 0.22872(19) 0.0242(6) Uani 1 1 d . . . . .
O1 O 0.43184(13) 0.7033(2) 0.6026(2) 0.0290(6) Uani 1 1 d . . . . .
H1 H 0.447997 0.693326 0.664145 0.043 Uiso 1 1 calc R U . . .
O5 O 0.06925(13) 0.1555(3) 0.1447(2) 0.0312(7) Uani 1 1 d . . . . .
H5A H 0.053139 0.135079 0.188162 0.047 Uiso 1 1 calc R U . . .
O2 O 0.51573(16) 1.1614(3) 0.6915(2) 0.0431(8) Uani 1 1 d . . . . .
N1 N 0.44991(15) 1.0557(3) 0.5618(2) 0.0245(7) Uani 1 1 d . . . . .
O6 O -0.01101(17) 0.6104(3) 0.2053(3) 0.0495(9) Uani 1 1 d . . . . .
N2 N 0.04997(15) 0.5141(3) 0.1257(3) 0.0265(7) Uani 1 1 d . . . . .
C32 C 0.17226(17) 0.1915(3) 0.1260(3) 0.0225(8) Uani 1 1 d . . . . .
C12 C 0.37140(17) 0.7601(3) 0.5831(3) 0.0220(8) Uani 1 1 d . . . . .
C11 C 0.32964(17) 0.7297(3) 0.4756(3) 0.0221(8) Uani 1 1 d . . . . .
C37 C 0.20880(17) 0.2836(3) 0.1062(3) 0.0224(8) Uani 1 1 d . . . . .
C10 C 0.28990(17) 0.8150(3) 0.4154(3) 0.0223(8) Uani 1 1 d . . . . .
C40 C 0.07922(18) 0.4026(3) 0.1072(3) 0.0228(8) Uani 1 1 d . . . . .
H40 H 0.046679 0.349675 0.064574 0.027 Uiso 1 1 calc R U . . .
C7 C 0.41927(17) 0.9414(3) 0.5251(3) 0.0213(8) Uani 1 1 d . . . . .
H7 H 0.450375 0.884641 0.515797 0.026 Uiso 1 1 calc R U . . .
C6 C 0.42593(18) 1.1452(3) 0.4889(3) 0.0243(8) Uani 1 1 d . . . . .
C13 C 0.38266(17) 0.8944(3) 0.5955(3) 0.0212(8) Uani 1 1 d . . . . .
C14 C 0.41582(19) 0.9313(4) 0.7057(3) 0.0266(8) Uani 1 1 d . . . . .
H14A H 0.393045 0.997168 0.721877 0.032 Uiso 1 1 calc R U . . .
H14B H 0.413629 0.867641 0.750696 0.032 Uiso 1 1 calc R U . . .
C38 C 0.19255(17) 0.4037(3) 0.1333(3) 0.0229(8) Uani 1 1 d . . . . .
H38 H 0.226795 0.459286 0.134768 0.027 Uiso 1 1 calc R U . . .
C46 C 0.11677(18) 0.5692(3) 0.0359(3) 0.0259(8) Uani 1 1 d . . . . .
C30 C 0.11818(18) 0.3442(4) 0.2068(3) 0.0253(8) Uani 1 1 d . . . . .
C9 C 0.30488(17) 0.9399(3) 0.4476(3) 0.0219(8) Uani 1 1 d . . . . .
H9 H 0.269315 0.991711 0.412173 0.026 Uiso 1 1 calc R U . . .
C17 C 0.3249(2) 0.6158(4) 0.4402(3) 0.0282(9) Uani 1 1 d . . . . .
H17 H 0.352675 0.559409 0.478291 0.034 Uiso 1 1 calc R U . . .
C39 C 0.12805(17) 0.4396(3) 0.0533(3) 0.0225(8) Uani 1 1 d . . . . .
H39 H 0.120951 0.397687 -0.011070 0.027 Uiso 1 1 calc R U . . .
C31 C 0.12934(18) 0.2100(3) 0.1927(3) 0.0246(8) Uani 1 1 d . . . . .
C41 C 0.07172(18) 0.6090(3) 0.0796(3) 0.0260(8) Uani 1 1 d . . . . .
C8 C 0.36746(17) 0.9722(3) 0.4230(3) 0.0215(8) Uani 1 1 d . . . . .
H8 H 0.372364 0.924780 0.366936 0.026 Uiso 1 1 calc R U . . .
C21 C 0.3355(2) 0.7144(4) 0.6543(3) 0.0282(9) Uani 1 1 d . . . . .
H21A H 0.326929 0.632712 0.642206 0.042 Uiso 1 1 calc R U . . .
H21B H 0.295609 0.755671 0.641484 0.042 Uiso 1 1 calc R U . . .
H21C H 0.361369 0.726133 0.723843 0.042 Uiso 1 1 calc R U . . .
C36 C 0.25388(19) 0.2633(4) 0.0563(3) 0.0279(8) Uani 1 1 d . . . . .
H36 H 0.278720 0.324415 0.045127 0.033 Uiso 1 1 calc R U . . .
C19 C 0.2381(2) 0.6691(4) 0.2914(3) 0.0307(9) Uani 1 1 d . . . . .
H19 H 0.206294 0.648153 0.231575 0.037 Uiso 1 1 calc R U . . .
C1 C 0.37727(18) 1.0995(3) 0.4066(3) 0.0244(8) Uani 1 1 d . . . . .
C20 C 0.24438(19) 0.7840(4) 0.3236(3) 0.0276(8) Uani 1 1 d . . . . .
H20 H 0.218016 0.840899 0.283628 0.033 Uiso 1 1 calc R U . . .
C27 C 0.0160(2) 0.5197(4) 0.1911(4) 0.0347(10) Uani 1 1 d . . . . .
C18 C 0.2795(2) 0.5851(4) 0.3490(3) 0.0323(9) Uani 1 1 d . . . . .
H18 H 0.276752 0.508374 0.326292 0.039 Uiso 1 1 calc R U . . .
C2 C 0.3465(2) 1.1691(4) 0.3257(3) 0.0319(9) Uani 1 1 d . . . . .
H2 H 0.314051 1.138834 0.270599 0.038 Uiso 1 1 calc R U . . .
C29 C 0.0899(2) 0.3711(4) 0.2924(3) 0.0324(9) Uani 1 1 d . . . . .
H29A H 0.114828 0.432518 0.335106 0.039 Uiso 1 1 calc R U . . .
H29B H 0.092902 0.302279 0.334358 0.039 Uiso 1 1 calc R U . . .
C15 C 0.4860(2) 0.9647(4) 0.7250(3) 0.0320(9) Uani 1 1 d . . . . .
H15A H 0.506103 0.983602 0.796350 0.038 Uiso 1 1 calc R U . . .
H15B H 0.509290 0.900284 0.707596 0.038 Uiso 1 1 calc R U . . .
C33 C 0.1806(2) 0.0810(4) 0.0921(3) 0.0293(9) Uani 1 1 d . . . . .
H33 H 0.156355 0.019524 0.104461 0.035 Uiso 1 1 calc R U . . .
C42 C 0.05369(19) 0.7248(4) 0.0747(3) 0.0332(10) Uani 1 1 d . . . . .
H42 H 0.023737 0.751103 0.104687 0.040 Uiso 1 1 calc R U . . .
C50 C 0.1637(2) 0.1528(4) 0.2949(3) 0.0336(10) Uani 1 1 d . . . . .
H50A H 0.135890 0.152846 0.336456 0.050 Uiso 1 1 calc R U . . .
H50B H 0.202131 0.195603 0.328636 0.050 Uiso 1 1 calc R U . . .
H50C H 0.174675 0.074043 0.283812 0.050 Uiso 1 1 calc R U . . .
C16 C 0.48746(19) 1.0693(4) 0.6594(3) 0.0304(9) Uani 1 1 d . . . . .
C5 C 0.4444(2) 1.2606(4) 0.4915(3) 0.0312(9) Uani 1 1 d . . . . .
H5 H 0.476851 1.290753 0.546573 0.037 Uiso 1 1 calc R U . . .
C34 C 0.2243(2) 0.0601(4) 0.0400(3) 0.0344(10) Uani 1 1 d . . . . .
H34 H 0.228579 -0.014441 0.016378 0.041 Uiso 1 1 calc R U . . .
C45 C 0.1449(2) 0.6450(4) -0.0146(4) 0.0372(10) Uani 1 1 d . . . . .
H45 H 0.175244 0.618125 -0.043700 0.045 Uiso 1 1 calc R U . . .
C35 C 0.2618(2) 0.1512(4) 0.0231(3) 0.0348(10) Uani 1 1 d . . . . .
H35 H 0.292015 0.137359 -0.010090 0.042 Uiso 1 1 calc R U . . .
C43 C 0.0822(2) 0.8002(4) 0.0231(4) 0.0396(11) Uani 1 1 d . . . . .
H43 H 0.070449 0.878415 0.018409 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3642(2) 1.2856(4) 0.3266(4) 0.0383(10) Uani 1 1 d . . . . .
H3 H 0.343423 1.333799 0.272178 0.046 Uiso 1 1 calc R U . . .
C4 C 0.4127(2) 1.3298(4) 0.4086(4) 0.0370(10) Uani 1 1 d . . . . .
H4 H 0.424323 1.407655 0.408157 0.044 Uiso 1 1 calc R U . . .
C44 C 0.1274(2) 0.7638(4) -0.0219(4) 0.0413(11) Uani 1 1 d . . . . .
H44 H 0.145730 0.816406 -0.055916 0.050 Uiso 1 1 calc R U . . .
C28 C 0.0190(2) 0.4096(4) 0.2503(4) 0.0398(11) Uani 1 1 d . . . . .
H28A H -0.006303 0.349342 0.206551 0.048 Uiso 1 1 calc R U . . .
H28B H 0.001738 0.422616 0.305993 0.048 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
O3 C13 1.443(4) . ?
O3 C9 1.439(4) . ?
O4 C38 1.432(4) . ?
O4 C30 1.445(4) . ?
O1 H1 0.8200 . ?
O1 C12 1.424(4) . ?
O5 H5A 0.8200 . ?
O5 C31 1.420(4) . ?
O2 C16 1.235(5) . ?
N1 C7 1.488(5) . ?
N1 C6 1.420(5) . ?
N1 C16 1.350(5) . ?
O6 C27 1.243(5) . ?
N2 C40 1.488(5) . ?
N2 C41 1.418(5) . ?
N2 C27 1.341(5) . ?
C32 C37 1.403(5) . ?
C32 C31 1.524(5) . ?
C32 C33 1.383(5) . ?
C12 C11 1.521(5) . ?
C12 C13 1.562(5) . ?
C12 C21 1.533(5) . ?
C11 C10 1.397(5) . ?
C11 C17 1.388(5) . ?
C37 C38 1.501(5) . ?
C37 C36 1.390(5) . ?
C10 C9 1.507(5) . ?
C10 C20 1.391(5) . ?
C40 H40 0.9800 . ?
C40 C30 1.529(5) . ?
C40 C39 1.543(5) . ?
C7 H7 0.9800 . ?
C7 C13 1.539(5) . ?
C7 C8 1.549(5) . ?
C6 C1 1.394(5) . ?
C6 C5 1.382(6) . ?
C13 C14 1.527(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.525(6) . ?
C38 H38 0.9800 . ?
C38 C39 1.552(5) . ?
C46 C39 1.514(5) . ?
C46 C41 1.386(5) . ?
C46 C45 1.377(6) . ?
C30 C31 1.581(5) . ?
C30 C29 1.529(5) . ?
C9 H9 0.9800 . ?
C9 C8 1.557(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(6) . ?
C39 H39 0.9800 . ?
C31 C50 1.525(6) . ?
C41 C42 1.382(6) . ?
C8 H8 0.9800 . ?
C8 C1 1.505(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C36 H36 0.9300 . ?
C36 C35 1.395(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(6) . ?
C19 C18 1.391(6) . ?
C1 C2 1.368(6) . ?
C20 H20 0.9300 . ?
C27 C28 1.495(6) . ?
C18 H18 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.391(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C28 1.542(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.511(6) . ?
C33 H33 0.9300 . ?
C33 C34 1.390(6) . ?
C42 H42 0.9300 . ?
C42 C43 1.387(6) . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C4 1.387(6) . ?
C34 H34 0.9300 . ?
C34 C35 1.394(6) . ?
C45 H45 0.9300 . ?
C45 C44 1.411(6) . ?
C35 H35 0.9300 . ?
C43 H43 0.9300 . ?
C43 C44 1.390(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(7) . ?
C4 H4 0.9300 . ?
C44 H44 0.9300 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?

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
C9 O3 C13 104.2(3) . . ?
C38 O4 C30 104.7(3) . . ?
C12 O1 H1 109.5 . . ?
C31 O5 H5A 109.5 . . ?
C6 N1 C7 111.6(3) . . ?
C16 N1 C7 120.7(3) . . ?
C16 N1 C6 126.8(3) . . ?
C41 N2 C40 111.0(3) . . ?
C27 N2 C40 121.2(3) . . ?
C27 N2 C41 127.0(3) . . ?
C37 C32 C31 120.7(3) . . ?
C33 C32 C37 118.7(4) . . ?
C33 C32 C31 120.3(3) . . ?
O1 C12 C11 108.6(3) . . ?
O1 C12 C13 109.0(3) . . ?
O1 C12 C21 110.9(3) . . ?
C11 C12 C13 111.0(3) . . ?
C11 C12 C21 106.0(3) . . ?
C21 C12 C13 111.3(3) . . ?
C10 C11 C12 119.5(3) . . ?
C17 C11 C12 121.0(3) . . ?
C17 C11 C10 119.1(3) . . ?
C32 C37 C38 116.6(3) . . ?
C36 C37 C32 120.6(4) . . ?
C36 C37 C38 122.6(3) . . ?
C11 C10 C9 116.9(3) . . ?
C20 C10 C11 119.9(3) . . ?
C20 C10 C9 122.7(3) . . ?
N2 C40 H40 111.4 . . ?
N2 C40 C30 111.7(3) . . ?
N2 C40 C39 104.4(3) . . ?
C30 C40 H40 111.4 . . ?
C30 C40 C39 106.3(3) . . ?
C39 C40 H40 111.4 . . ?
N1 C7 H7 111.9 . . ?
N1 C7 C13 111.2(3) . . ?
N1 C7 C8 103.5(3) . . ?
C13 C7 H7 111.9 . . ?
C13 C7 C8 106.1(3) . . ?
C8 C7 H7 111.9 . . ?
C1 C6 N1 109.0(3) . . ?
C5 C6 N1 129.4(4) . . ?
C5 C6 C1 121.6(4) . . ?
O3 C13 C12 108.0(3) . . ?
O3 C13 C7 102.5(3) . . ?
O3 C13 C14 110.2(3) . . ?
C7 C13 C12 111.8(3) . . ?
C14 C13 C12 113.1(3) . . ?
C14 C13 C7 110.8(3) . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 C13 112.5(3) . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
O4 C38 C37 110.3(3) . . ?
O4 C38 H38 111.2 . . ?
O4 C38 C39 105.2(3) . . ?
C37 C38 H38 111.2 . . ?
C37 C38 C39 107.4(3) . . ?
C39 C38 H38 111.2 . . ?
C41 C46 C39 111.0(3) . . ?
C45 C46 C39 128.6(4) . . ?
C45 C46 C41 120.4(4) . . ?
O4 C30 C40 102.0(3) . . ?
O4 C30 C31 107.5(3) . . ?
O4 C30 C29 108.9(3) . . ?
C40 C30 C31 112.3(3) . . ?
C40 C30 C29 111.2(3) . . ?
C29 C30 C31 114.1(3) . . ?
O3 C9 C10 110.8(3) . . ?
O3 C9 H9 111.3 . . ?
O3 C9 C8 105.2(3) . . ?
C10 C9 H9 111.3 . . ?
C10 C9 C8 106.7(3) . . ?
C8 C9 H9 111.3 . . ?
C11 C17 H17 119.5 . . ?
C18 C17 C11 120.9(4) . . ?
C18 C17 H17 119.5 . . ?
C40 C39 C38 101.4(3) . . ?
C40 C39 H39 111.5 . . ?
C38 C39 H39 111.5 . . ?
C46 C39 C40 104.1(3) . . ?
C46 C39 C38 116.1(3) . . ?
C46 C39 H39 111.5 . . ?
O5 C31 C32 108.3(3) . . ?
O5 C31 C30 109.3(3) . . ?
O5 C31 C50 111.0(3) . . ?
C32 C31 C30 111.1(3) . . ?
C50 C31 C32 106.3(3) . . ?
C50 C31 C30 110.8(3) . . ?
C46 C41 N2 109.2(3) . . ?
C42 C41 N2 129.0(4) . . ?
C42 C41 C46 121.8(4) . . ?
C7 C8 C9 101.0(3) . . ?
C7 C8 H8 111.3 . . ?
C9 C8 H8 111.3 . . ?
C1 C8 C7 105.1(3) . . ?
C1 C8 C9 116.1(3) . . ?
C1 C8 H8 111.3 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C37 C36 H36 120.0 . . ?
C37 C36 C35 119.9(4) . . ?
C35 C36 H36 120.0 . . ?
C20 C19 H19 120.2 . . ?
C20 C19 C18 119.6(4) . . ?
C18 C19 H19 120.2 . . ?
C6 C1 C8 110.5(3) . . ?
C2 C1 C6 120.2(4) . . ?
C2 C1 C8 129.3(4) . . ?
C10 C20 H20 119.8 . . ?
C19 C20 C10 120.5(4) . . ?
C19 C20 H20 119.8 . . ?
O6 C27 N2 122.6(4) . . ?
O6 C27 C28 124.3(4) . . ?
N2 C27 C28 113.0(4) . . ?
C17 C18 C19 119.9(4) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.2(4) . . ?
C3 C2 H2 120.4 . . ?
C30 C29 H29A 109.3 . . ?
C30 C29 H29B 109.3 . . ?
C30 C29 C28 111.8(4) . . ?
H29A C29 H29B 107.9 . . ?
C28 C29 H29A 109.3 . . ?
C28 C29 H29B 109.3 . . ?
C14 C15 H15A 110.2 . . ?
C14 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 C14 107.7(3) . . ?
C16 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
C32 C33 H33 119.4 . . ?
C32 C33 C34 121.3(4) . . ?
C34 C33 H33 119.4 . . ?
C41 C42 H42 121.4 . . ?
C41 C42 C43 117.2(4) . . ?
C43 C42 H42 121.4 . . ?
C31 C50 H50A 109.5 . . ?
C31 C50 H50B 109.5 . . ?
C31 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
O2 C16 N1 122.5(4) . . ?
O2 C16 C15 124.5(4) . . ?
N1 C16 C15 112.8(3) . . ?
C6 C5 H5 121.3 . . ?
C6 C5 C4 117.4(4) . . ?
C4 C5 H5 121.3 . . ?
C33 C34 H34 120.1 . . ?
C33 C34 C35 119.7(4) . . ?
C35 C34 H34 120.1 . . ?
C46 C45 H45 120.3 . . ?
C46 C45 C44 119.4(4) . . ?
C44 C45 H45 120.3 . . ?
C36 C35 H35 120.1 . . ?
C34 C35 C36 119.8(4) . . ?
C34 C35 H35 120.1 . . ?
C42 C43 H43 118.6 . . ?
C42 C43 C44 122.8(4) . . ?
C44 C43 H43 118.6 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C5 C4 H4 119.2 . . ?
C3 C4 C5 121.6(4) . . ?
C3 C4 H4 119.2 . . ?
C45 C44 H44 120.8 . . ?
C43 C44 C45 118.3(4) . . ?
C43 C44 H44 120.8 . . ?
C27 C28 C29 108.3(4) . . ?
C27 C28 H28A 110.0 . . ?
C27 C28 H28B 110.0 . . ?
C29 C28 H28A 110.0 . . ?
C29 C28 H28B 110.0 . . ?
H28A C28 H28B 108.4 . . ?

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 C13 C14 C15 -133.2(3) . . . . ?
O3 C9 C8 C7 26.0(3) . . . . ?
O3 C9 C8 C1 -87.0(4) . . . . ?
O4 C38 C39 C40 -23.6(3) . . . . ?
O4 C38 C39 C46 88.4(4) . . . . ?
O4 C30 C31 O5 -164.4(3) . . . . ?
O4 C30 C31 C32 -45.0(4) . . . . ?
O4 C30 C31 C50 73.0(4) . . . . ?
O4 C30 C29 C28 132.3(4) . . . . ?
O1 C12 C11 C10 -141.5(3) . . . . ?
O1 C12 C11 C17 45.7(5) . . . . ?
O1 C12 C13 O3 169.0(3) . . . . ?
O1 C12 C13 C7 56.9(4) . . . . ?
O1 C12 C13 C14 -68.9(4) . . . . ?
N1 C7 C13 O3 84.9(3) . . . . ?
N1 C7 C13 C12 -159.7(3) . . . . ?
N1 C7 C13 C14 -32.6(4) . . . . ?
N1 C7 C8 C9 -116.4(3) . . . . ?
N1 C7 C8 C1 4.8(4) . . . . ?
N1 C6 C1 C8 -0.5(4) . . . . ?
N1 C6 C1 C2 -179.8(4) . . . . ?
N1 C6 C5 C4 179.7(4) . . . . ?
O6 C27 C28 C29 -127.4(5) . . . . ?
N2 C40 C30 O4 -84.8(3) . . . . ?
N2 C40 C30 C31 160.4(3) . . . . ?
N2 C40 C30 C29 31.1(4) . . . . ?
N2 C40 C39 C38 115.0(3) . . . . ?
N2 C40 C39 C46 -5.9(4) . . . . ?
N2 C41 C42 C43 -179.1(4) . . . . ?
N2 C27 C28 C29 47.7(5) . . . . ?
C32 C37 C38 O4 40.7(4) . . . . ?
C32 C37 C38 C39 -73.4(4) . . . . ?
C32 C37 C36 C35 1.7(6) . . . . ?
C32 C33 C34 C35 1.4(6) . . . . ?
C12 C11 C10 C9 17.9(5) . . . . ?
C12 C11 C10 C20 -170.0(3) . . . . ?
C12 C11 C17 C18 169.7(4) . . . . ?
C12 C13 C14 C15 105.9(4) . . . . ?
C11 C12 C13 O3 49.4(4) . . . . ?
C11 C12 C13 C7 -62.7(4) . . . . ?
C11 C12 C13 C14 171.5(3) . . . . ?
C11 C10 C9 O3 -41.7(4) . . . . ?
C11 C10 C9 C8 72.2(4) . . . . ?
C11 C10 C20 C19 0.1(6) . . . . ?
C11 C17 C18 C19 0.3(6) . . . . ?
C37 C32 C31 O5 135.5(3) . . . . ?
C37 C32 C31 C30 15.5(5) . . . . ?
C37 C32 C31 C50 -105.1(4) . . . . ?
C37 C32 C33 C34 0.4(6) . . . . ?
C37 C38 C39 C40 93.9(3) . . . . ?
C37 C38 C39 C46 -154.1(3) . . . . ?
C37 C36 C35 C34 0.2(6) . . . . ?
C10 C11 C17 C18 -3.1(6) . . . . ?
C10 C9 C8 C7 -91.6(3) . . . . ?
C10 C9 C8 C1 155.3(3) . . . . ?
C40 N2 C41 C46 -3.4(4) . . . . ?
C40 N2 C41 C42 176.4(4) . . . . ?
C40 N2 C27 O6 -177.2(4) . . . . ?
C40 N2 C27 C28 7.6(6) . . . . ?
C40 C30 C31 O5 -52.9(4) . . . . ?
C40 C30 C31 C32 66.5(4) . . . . ?
C40 C30 C31 C50 -175.6(3) . . . . ?
C40 C30 C29 C28 20.6(5) . . . . ?
C7 N1 C6 C1 3.9(4) . . . . ?
C7 N1 C6 C5 -176.0(4) . . . . ?
C7 N1 C16 O2 177.0(4) . . . . ?
C7 N1 C16 C15 -8.0(5) . . . . ?
C7 C13 C14 C15 -20.5(4) . . . . ?
C7 C8 C1 C6 -2.8(4) . . . . ?
C7 C8 C1 C2 176.5(4) . . . . ?
C6 N1 C7 C13 -118.9(3) . . . . ?
C6 N1 C7 C8 -5.4(4) . . . . ?
C6 N1 C16 O2 -14.3(7) . . . . ?
C6 N1 C16 C15 160.7(4) . . . . ?
C6 C1 C2 C3 -0.1(6) . . . . ?
C6 C5 C4 C3 0.3(7) . . . . ?
C13 O3 C9 C10 69.6(3) . . . . ?
C13 O3 C9 C8 -45.2(3) . . . . ?
C13 C12 C11 C10 -21.6(5) . . . . ?
C13 C12 C11 C17 165.6(3) . . . . ?
C13 C7 C8 C9 0.8(3) . . . . ?
C13 C7 C8 C1 121.9(3) . . . . ?
C13 C14 C15 C16 62.8(4) . . . . ?
C14 C15 C16 O2 126.8(4) . . . . ?
C14 C15 C16 N1 -48.1(5) . . . . ?
C38 O4 C30 C40 -44.6(3) . . . . ?
C38 O4 C30 C31 73.8(3) . . . . ?
C38 O4 C30 C29 -162.1(3) . . . . ?
C38 C37 C36 C35 -172.9(4) . . . . ?
C46 C41 C42 C43 0.6(6) . . . . ?
C46 C45 C44 C43 0.3(7) . . . . ?
C30 O4 C38 C37 -71.9(3) . . . . ?
C30 O4 C38 C39 43.6(3) . . . . ?
C30 C40 C39 C38 -3.2(4) . . . . ?
C30 C40 C39 C46 -124.1(3) . . . . ?
C30 C29 C28 C27 -62.3(5) . . . . ?
C9 O3 C13 C12 -73.7(3) . . . . ?
C9 O3 C13 C7 44.4(3) . . . . ?
C9 O3 C13 C14 162.4(3) . . . . ?
C9 C10 C20 C19 171.7(4) . . . . ?
C9 C8 C1 C6 107.8(4) . . . . ?
C9 C8 C1 C2 -72.9(5) . . . . ?
C17 C11 C10 C9 -169.2(3) . . . . ?
C17 C11 C10 C20 2.9(5) . . . . ?
C39 C40 C30 O4 28.4(4) . . . . ?
C39 C40 C30 C31 -86.4(4) . . . . ?
C39 C40 C30 C29 144.4(3) . . . . ?
C39 C46 C41 N2 -0.7(4) . . . . ?
C39 C46 C41 C42 179.4(4) . . . . ?
C39 C46 C45 C44 -179.9(4) . . . . ?
C31 C32 C37 C38 -13.2(5) . . . . ?
C31 C32 C37 C36 171.8(3) . . . . ?
C31 C32 C33 C34 -173.5(4) . . . . ?
C31 C30 C29 C28 -107.7(4) . . . . ?
C41 N2 C40 C30 120.3(3) . . . . ?
C41 N2 C40 C39 5.9(4) . . . . ?
C41 N2 C27 O6 13.8(7) . . . . ?
C41 N2 C27 C28 -161.4(4) . . . . ?
C41 C46 C39 C40 4.3(4) . . . . ?
C41 C46 C39 C38 -106.1(4) . . . . ?
C41 C46 C45 C44 -0.2(7) . . . . ?
C41 C42 C43 C44 -0.5(7) . . . . ?
C8 C7 C13 O3 -26.9(3) . . . . ?
C8 C7 C13 C12 88.5(3) . . . . ?
C8 C7 C13 C14 -144.4(3) . . . . ?
C8 C1 C2 C3 -179.4(4) . . . . ?
C21 C12 C11 C10 99.4(4) . . . . ?
C21 C12 C11 C17 -73.4(4) . . . . ?
C21 C12 C13 O3 -68.5(4) . . . . ?
C21 C12 C13 C7 179.5(3) . . . . ?
C21 C12 C13 C14 53.6(4) . . . . ?
C36 C37 C38 O4 -144.4(3) . . . . ?
C36 C37 C38 C39 101.4(4) . . . . ?
C1 C6 C5 C4 -0.2(6) . . . . ?
C1 C2 C3 C4 0.3(7) . . . . ?
C20 C10 C9 O3 146.4(3) . . . . ?
C20 C10 C9 C8 -99.7(4) . . . . ?
C20 C19 C18 C17 2.8(6) . . . . ?
C27 N2 C40 C30 -50.3(5) . . . . ?
C27 N2 C40 C39 -164.7(4) . . . . ?
C27 N2 C41 C46 166.6(4) . . . . ?
C27 N2 C41 C42 -13.6(7) . . . . ?
C18 C19 C20 C10 -3.0(6) . . . . ?
C2 C3 C4 C5 -0.5(7) . . . . ?
C29 C30 C31 O5 74.7(4) . . . . ?
C29 C30 C31 C32 -165.8(3) . . . . ?
C29 C30 C31 C50 -47.9(4) . . . . ?
C33 C32 C37 C38 173.0(3) . . . . ?
C33 C32 C37 C36 -2.0(6) . . . . ?
C33 C32 C31 O5 -50.7(5) . . . . ?
C33 C32 C31 C30 -170.7(3) . . . . ?
C33 C32 C31 C50 68.7(4) . . . . ?
C33 C34 C35 C36 -1.7(7) . . . . ?
C42 C43 C44 C45 0.1(7) . . . . ?
C16 N1 C7 C13 51.4(5) . . . . ?
C16 N1 C7 C8 164.9(3) . . . . ?
C16 N1 C6 C1 -165.7(4) . . . . ?
C16 N1 C6 C5 14.4(7) . . . . ?
C5 C6 C1 C8 179.4(4) . . . . ?
C5 C6 C1 C2 0.1(6) . . . . ?
C45 C46 C39 C40 -176.0(4) . . . . ?
C45 C46 C39 C38 73.6(5) . . . . ?
C45 C46 C41 N2 179.5(4) . . . . ?
C45 C46 C41 C42 -0.3(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 4.307
_oxdiff_exptl_absorpt_empirical_full_min 0.684
####################################################################### 
# 
# 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_71-74
_database_code_depnum_ccdc_archive 'CCDC 2189547'
loop_
_audit_author_name
_audit_author_address
'Rao Weidong'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2021-05-15
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 N O3'
_chemical_formula_sum            'C20 H15 N O3'
_chemical_formula_weight         317.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.8645(7)
_cell_length_b                   15.3909(10)
_cell_length_c                   8.9312(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.325(7)
_cell_angle_gamma                90
_cell_volume                     1446.99(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2448
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      28.3960
_cell_measurement_theta_min      2.6250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6326
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.344
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00   7.00   1.00    1.20    --  -11.27 -38.00  60.00   61
  2  ω    -47.00  24.00   1.00    1.20    --   11.90 -38.00-180.00   71
  3  ω    -16.00  47.00   1.00    1.20    --   11.90 -99.00 -30.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0659050000
_diffrn_orient_matrix_UB_12      0.0090326000
_diffrn_orient_matrix_UB_13      -0.0253275000
_diffrn_orient_matrix_UB_21      -0.0094216000
_diffrn_orient_matrix_UB_22      -0.0400222000
_diffrn_orient_matrix_UB_23      -0.0406814000
_diffrn_orient_matrix_UB_31      -0.0103674000
_diffrn_orient_matrix_UB_32      -0.0210200000
_diffrn_orient_matrix_UB_33      0.0664611000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2050
_reflns_number_total             2558
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.051
_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     217
_refine_ls_number_reflns         2558
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0408
_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)+(0.0462P)²+0.2152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1020
_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), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44262(10) 0.65924(7) 0.53922(11) 0.0224(3) Uani 1 1 d . . . . .
O2 O 0.47824(11) 0.48382(8) 0.79686(13) 0.0317(3) Uani 1 1 d . . . . .
O3 O 0.01603(12) 0.57882(9) 0.34521(15) 0.0444(4) Uani 1 1 d . . . . .
N1 N 0.16402(13) 0.64863(10) 0.53165(15) 0.0267(3) Uani 1 1 d . . . . .
C1 C 0.13450(15) 0.73682(12) 0.49431(18) 0.0260(4) Uani 1 1 d . . . . .
C2 C 0.03151(16) 0.77107(13) 0.3863(2) 0.0332(5) Uani 1 1 d . . . . .
H2 H -0.029984 0.735309 0.325403 0.040 Uiso 1 1 calc R U . . .
C3 C 0.02405(17) 0.86088(13) 0.3727(2) 0.0360(5) Uani 1 1 d . . . . .
H3 H -0.044482 0.885564 0.302020 0.043 Uiso 1 1 calc R U . . .
C4 C 0.11522(16) 0.91450(13) 0.4610(2) 0.0329(4) Uani 1 1 d . . . . .
H4 H 0.107539 0.974476 0.449896 0.039 Uiso 1 1 calc R U . . .
C5 C 0.21887(16) 0.87879(12) 0.56696(19) 0.0289(4) Uani 1 1 d . . . . .
H5 H 0.281533 0.914522 0.625767 0.035 Uiso 1 1 calc R U . . .
C6 C 0.22746(15) 0.78970(12) 0.58359(17) 0.0238(4) Uani 1 1 d . . . . .
C7 C 0.32832(15) 0.73616(11) 0.69012(17) 0.0230(4) Uani 1 1 d . . . . .
H7 H 0.339260 0.753332 0.798283 0.028 Uiso 1 1 calc R U . . .
C8 C 0.45811(15) 0.73100(11) 0.64594(17) 0.0219(4) Uani 1 1 d . . . . .
H8 H 0.475794 0.785023 0.597052 0.026 Uiso 1 1 calc R U . . .
C9 C 0.56422(15) 0.70947(11) 0.78488(17) 0.0218(4) Uani 1 1 d . . . . .
C10 C 0.64943(15) 0.77118(12) 0.86314(18) 0.0252(4) Uani 1 1 d . . . . .
H10 H 0.642345 0.828780 0.830658 0.030 Uiso 1 1 calc R U . . .
C11 C 0.74498(16) 0.74669(12) 0.98967(19) 0.0295(4) Uani 1 1 d . . . . .
H11 H 0.803090 0.787909 1.040418 0.035 Uiso 1 1 calc R U . . .
C12 C 0.75514(16) 0.66154(12) 1.04168(19) 0.0299(4) Uani 1 1 d . . . . .
H12 H 0.819942 0.645754 1.126521 0.036 Uiso 1 1 calc R U . . .
C13 C 0.66896(15) 0.60037(12) 0.96731(18) 0.0264(4) Uani 1 1 d . . . . .
H13 H 0.674222 0.543500 1.003521 0.032 Uiso 1 1 calc R U . . .
C14 C 0.57371(14) 0.62369(11) 0.83761(17) 0.0225(4) Uani 1 1 d . . . . .
C15 C 0.48106(15) 0.55912(11) 0.75499(18) 0.0229(4) Uani 1 1 d . . . . .
C16 C 0.38402(15) 0.59223(11) 0.61048(17) 0.0219(4) Uani 1 1 d . . . . .
C17 C 0.27803(15) 0.64229(11) 0.66158(17) 0.0229(4) Uani 1 1 d . . . . .
H17 H 0.258950 0.616759 0.753810 0.028 Uiso 1 1 calc R U . . .
C18 C 0.11343(16) 0.57707(12) 0.4495(2) 0.0332(5) Uani 1 1 d . . . . .
C19 C 0.19527(18) 0.49789(12) 0.4946(2) 0.0361(5) Uani 1 1 d . . . . .
H19A H 0.164732 0.451233 0.421944 0.043 Uiso 1 1 calc R U . . .
H19B H 0.191034 0.478529 0.596608 0.043 Uiso 1 1 calc R U . . .
C20 C 0.33286(16) 0.52008(12) 0.49513(19) 0.0286(4) Uani 1 1 d . . . . .
H20A H 0.385411 0.468705 0.521973 0.034 Uiso 1 1 calc R U . . .
H20B H 0.336792 0.538407 0.392497 0.034 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 C8 1.4412(18) . ?
O1 C16 1.4403(19) . ?
O2 C15 1.221(2) . ?
O3 C18 1.225(2) . ?
N1 C1 1.415(2) . ?
N1 C17 1.476(2) . ?
N1 C18 1.362(2) . ?
C1 C2 1.388(2) . ?
C1 C6 1.386(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 C7 1.506(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.557(2) . ?
C7 C17 1.543(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.507(2) . ?
C9 C10 1.388(2) . ?
C9 C14 1.397(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.396(2) . ?
C14 C15 1.476(2) . ?
C15 C16 1.537(2) . ?
C16 C17 1.545(2) . ?
C16 C20 1.523(2) . ?
C17 H17 0.9800 . ?
C18 C19 1.504(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.532(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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
C16 O1 C8 104.39(11) . . ?
C1 N1 C17 110.23(13) . . ?
C18 N1 C1 127.65(14) . . ?
C18 N1 C17 121.24(15) . . ?
C2 C1 N1 128.66(16) . . ?
C6 C1 N1 109.72(14) . . ?
C6 C1 C2 121.63(17) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.28(17) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 121.91(16) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.91(18) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.16(17) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 110.78(15) . . ?
C5 C6 C1 120.10(15) . . ?
C5 C6 C7 129.11(15) . . ?
C6 C7 H7 111.5 . . ?
C6 C7 C8 115.51(13) . . ?
C6 C7 C17 103.61(13) . . ?
C8 C7 H7 111.5 . . ?
C17 C7 H7 111.5 . . ?
C17 C7 C8 102.48(12) . . ?
O1 C8 C7 103.98(12) . . ?
O1 C8 H8 111.0 . . ?
O1 C8 C9 108.45(13) . . ?
C7 C8 H8 111.0 . . ?
C9 C8 C7 111.02(12) . . ?
C9 C8 H8 111.0 . . ?
C10 C9 C8 122.89(15) . . ?
C10 C9 C14 119.50(15) . . ?
C14 C9 C8 117.59(15) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.78(17) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.84(17) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.78(16) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.03(17) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C15 118.92(14) . . ?
C13 C14 C9 120.03(16) . . ?
C13 C14 C15 121.04(16) . . ?
O2 C15 C14 123.51(15) . . ?
O2 C15 C16 120.53(15) . . ?
C14 C15 C16 115.96(14) . . ?
O1 C16 C15 108.78(12) . . ?
O1 C16 C17 102.51(13) . . ?
O1 C16 C20 110.51(12) . . ?
C15 C16 C17 108.89(12) . . ?
C20 C16 C15 112.69(14) . . ?
C20 C16 C17 112.91(13) . . ?
N1 C17 C7 105.18(13) . . ?
N1 C17 C16 110.03(12) . . ?
N1 C17 H17 112.1 . . ?
C7 C17 C16 104.85(12) . . ?
C7 C17 H17 112.1 . . ?
C16 C17 H17 112.1 . . ?
O3 C18 N1 123.34(18) . . ?
O3 C18 C19 124.35(17) . . ?
N1 C18 C19 112.19(15) . . ?
C18 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
C18 C19 C20 109.38(15) . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
C16 C20 C19 110.90(14) . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.0 . . ?

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 C8 C9 C10 143.41(14) . . . . ?
O1 C8 C9 C14 -38.16(18) . . . . ?
O1 C16 C17 N1 84.23(14) . . . . ?
O1 C16 C17 C7 -28.41(14) . . . . ?
O1 C16 C20 C19 -130.73(15) . . . . ?
O2 C15 C16 O1 -149.01(14) . . . . ?
O2 C15 C16 C17 99.99(17) . . . . ?
O2 C15 C16 C20 -26.1(2) . . . . ?
O3 C18 C19 C20 127.00(18) . . . . ?
N1 C1 C2 C3 179.50(16) . . . . ?
N1 C1 C6 C5 179.88(14) . . . . ?
N1 C1 C6 C7 -0.04(18) . . . . ?
N1 C18 C19 C20 -49.2(2) . . . . ?
C1 N1 C17 C7 -6.92(16) . . . . ?
C1 N1 C17 C16 -119.34(14) . . . . ?
C1 N1 C18 O3 -15.0(3) . . . . ?
C1 N1 C18 C19 161.23(15) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C6 C7 C8 107.10(16) . . . . ?
C1 C6 C7 C17 -4.12(16) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C2 C1 C6 C7 -179.61(14) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C4 C5 C6 C7 -179.35(15) . . . . ?
C5 C6 C7 C8 -72.8(2) . . . . ?
C5 C6 C7 C17 175.97(15) . . . . ?
C6 C1 C2 C3 -1.0(2) . . . . ?
C6 C7 C8 O1 -86.71(16) . . . . ?
C6 C7 C8 C9 156.86(14) . . . . ?
C6 C7 C17 N1 6.45(15) . . . . ?
C6 C7 C17 C16 122.50(12) . . . . ?
C7 C8 C9 C10 -102.95(17) . . . . ?
C7 C8 C9 C14 75.49(17) . . . . ?
C8 O1 C16 C15 -69.26(14) . . . . ?
C8 O1 C16 C17 45.94(14) . . . . ?
C8 O1 C16 C20 166.53(12) . . . . ?
C8 C7 C17 N1 -114.04(12) . . . . ?
C8 C7 C17 C16 2.01(15) . . . . ?
C8 C9 C10 C11 -179.76(14) . . . . ?
C8 C9 C14 C13 -179.00(14) . . . . ?
C8 C9 C14 C15 0.4(2) . . . . ?
C9 C10 C11 C12 -1.5(2) . . . . ?
C9 C14 C15 O2 -176.42(14) . . . . ?
C9 C14 C15 C16 2.8(2) . . . . ?
C10 C9 C14 C13 -0.5(2) . . . . ?
C10 C9 C14 C15 178.90(14) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 1.6(2) . . . . ?
C12 C13 C14 C9 -1.2(2) . . . . ?
C12 C13 C14 C15 179.37(15) . . . . ?
C13 C14 C15 O2 3.0(2) . . . . ?
C13 C14 C15 C16 -177.83(14) . . . . ?
C14 C9 C10 C11 1.8(2) . . . . ?
C14 C15 C16 O1 31.78(18) . . . . ?
C14 C15 C16 C17 -79.21(16) . . . . ?
C14 C15 C16 C20 154.69(14) . . . . ?
C15 C16 C17 N1 -160.65(13) . . . . ?
C15 C16 C17 C7 86.71(15) . . . . ?
C15 C16 C20 C19 107.33(16) . . . . ?
C16 O1 C8 C7 -45.19(14) . . . . ?
C16 O1 C8 C9 73.02(15) . . . . ?
C17 N1 C1 C2 -175.94(15) . . . . ?
C17 N1 C1 C6 4.53(18) . . . . ?
C17 N1 C18 O3 176.82(15) . . . . ?
C17 N1 C18 C19 -6.9(2) . . . . ?
C17 C7 C8 O1 25.17(14) . . . . ?
C17 C7 C8 C9 -91.26(15) . . . . ?
C17 C16 C20 C19 -16.57(19) . . . . ?
C18 N1 C1 C2 14.9(3) . . . . ?
C18 N1 C1 C6 -164.67(16) . . . . ?
C18 N1 C17 C7 163.10(14) . . . . ?
C18 N1 C17 C16 50.67(19) . . . . ?
C18 C19 C20 C16 60.41(18) . . . . ?
C20 C16 C17 N1 -34.68(18) . . . . ?
C20 C16 C17 C7 -147.32(13) . . . . ?

_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 1.234
_oxdiff_exptl_absorpt_empirical_full_min 0.754
