# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_zhuzf_190927
_database_code_depnum_ccdc_archive 'CCDC 1965911'
loop_
_audit_author_name
_audit_author_address
'Zefeng Zhu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N2 O'
_chemical_formula_sum            'C20 H20 N2 O'
_chemical_formula_weight         304.38
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.16300(10)
_cell_length_b                   12.1968(2)
_cell_length_c                   13.1905(2)
_cell_angle_alpha                103.4930(10)
_cell_angle_beta                 100.6160(10)
_cell_angle_gamma                96.617(2)
_cell_volume                     782.93(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14368
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.2210
_cell_measurement_theta_min      3.5350
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.834
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30393
_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         76.987
_diffrn_reflns_theta_min         3.531
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00 118.00   0.50    0.15    --   46.37  77.00   0.00  190
  2  ω     83.00 178.00   0.50    0.80    --  107.00 113.00  16.00  190
  3  ω    138.00 163.00   0.50    0.80    --  107.00  77.00 -30.00   50
  4  ω    134.00 169.00   0.50    0.80    --  107.00  77.00 -90.00   70
  5  ω    135.00 177.00   0.50    0.80    --  107.00 125.00 -30.00   84
  6  ω    111.00 137.00   0.50    0.80    --  107.00  45.00 -30.00   52
  7  ω     94.00 131.00   0.50    0.80    --  107.00  30.00-120.00   74
  8  ω    143.00 175.00   0.50    0.80    --  107.00  30.00-120.00   64
  9  ω     92.00 122.00   0.50    0.80    --  107.00  77.00 -30.00   60
 10  ω     84.00 125.00   0.50    0.80    --  107.00  77.00 -90.00   82
 11  ω     89.00 115.00   0.50    0.80    --  107.00 125.00 -30.00   52
 12  ω    110.00 171.00   0.50    0.80    --  107.00  61.00  60.00  122
 13  ω    110.00 136.00   0.50    0.80    --  107.00  45.00 150.00   52
 14  ω     84.00 156.00   0.50    0.80    --  107.00  77.00 120.00  144
 15  ω     91.00 149.00   0.50    0.80    --  107.00  61.00  90.00  116
 16  ω     82.00 125.00   0.50    0.80    --  107.00 -61.00  60.00   86
 17  ω     78.00 116.00   0.50    0.80    --  107.00-125.00  90.00   76
 18  ω     88.00 115.00   0.50    0.80    --  107.00-125.00   0.00   54
 19  ω     59.00  85.00   0.50    0.80    --  107.00 -94.00 -90.00   52
 20  ω     82.00 117.00   0.50    0.80    --  107.00-125.00-150.00   70
 21  ω     74.00 116.00   0.50    0.80    --  107.00-125.00 -90.00   84
 22  ω     34.00 112.00   0.50    0.80    --  107.00-113.00 -75.00  156
 23  ω     42.00  79.00   0.50    0.80    --  107.00-125.00   0.00   74
 24  ω     35.00 129.00   0.50    0.80    --  107.00 -77.00  60.00  188
 25  ω     48.00  74.00   0.50    0.80    --  107.00 -61.00  60.00   52
 26  ω     35.00  67.00   0.50    0.80    --  107.00-125.00  90.00   64
 27  ω     36.00 113.00   0.50    0.80    --  107.00-125.00  60.00  154
 28  ω     34.00 116.00   0.50    0.80    --  107.00 -61.00 -90.00  164
 29  ω     34.00  68.00   0.50    0.80    --  107.00-125.00 -90.00   68
 30  ω      6.00  89.00   0.50    0.15    --   46.37-113.00 -75.00  166
 31  ω     15.00  95.00   0.50    0.15    --   46.37-125.00 -90.00  160
 32  ω     26.00 121.00   0.50    0.15    --   48.00  74.00 -59.72  190
 33  ω     28.00 125.00   0.50    0.15    --   52.00  78.00  86.86  194
 34  ω     32.00 129.00   0.50    0.15    --   56.00  77.00 122.95  194
 35  ω     31.00 129.00   0.50    0.15    --   56.00  79.00 -52.35  196
 36  ω     22.00 121.00   0.50    0.15    --   48.00  83.00-138.72  198
 37  ω     18.00  45.00   0.50    0.15    --   48.00  90.00  29.46   54
 38  ω      4.00  33.00   0.50    0.15    --   36.00  95.00  80.30   58
 39  ω     19.00  45.00   0.50    0.15    --   48.00  88.00 142.94   52
 40  ω    -10.00  25.00   0.50    0.15    --   24.00  99.00  69.93   70
 41  ω    -21.00   6.00   0.50    0.15    --   16.00 104.00  58.27   54
 42  ω    -89.00  -2.00   0.50    0.15    --  -46.37 113.00  16.00  174
 43  ω    -78.00 -52.00   0.50    0.15    --  -72.00 -68.00  42.37   52
 44  ω    -78.00 -53.00   0.50    0.80    --  -80.00 -83.00  37.51   50
 45  ω    -79.00 -53.00   0.50    0.15    --  -72.00 -65.00 -48.92   52
 46  ω    -82.00 -50.00   0.50    0.80    --  -76.00 -81.00 -49.83   64
 47  ω    -94.00 -58.00   0.50    0.80    --  -80.00 -73.00 -90.34   72
 48  ω    -94.00 -65.00   0.50    0.80    --  -84.00 -64.00  -6.31   58
 49  ω    -93.00 -67.00   0.50    0.80    --  -84.00 -61.00 -24.53   52
 50  ω   -102.00 -69.00   0.50    0.80    --  -92.00 -74.00 -95.40   66
 51  ω    -93.00 -67.00   0.50    0.80    --  -84.00 -66.00-150.32   52
 52  ω    -94.00 -68.00   0.50    0.80    --  -88.00 -73.00-148.51   52
 53  ω   -101.00 -69.00   0.50    0.80    --  -96.00 -83.00 -83.89   64
 54  ω   -105.00 -79.00   0.50    0.80    -- -100.00 -74.00-131.55   52
 55  ω   -103.00 -77.00   0.50    0.80    -- -100.00 -74.00 -57.38   52
 56  ω   -106.00 -79.00   0.50    0.80    -- -100.00 -77.00 -30.00   54
 57  ω   -107.00 -80.00   0.50    0.80    -- -100.00 -67.00 -34.29   54
 58  ω   -106.00 -76.00   0.50    0.80    -- -100.00 -77.00   0.00   60
 59  ω   -103.00 -76.00   0.50    0.80    --  -96.00 -68.00  61.67   54
 60  ω   -103.00 -77.00   0.50    0.80    --  -96.00 -65.00 119.44   52
 61  ω    -79.00 -53.00   0.50    0.80    --  -76.00 -83.00 127.92   52
 62  ω    -94.00 -68.00   0.50    0.80    --  -88.00 -71.00 178.51   52
 63  ω   -105.00 -57.00   0.50    0.80    --  -80.00 -74.00 134.87   96
 64  ω   -101.00 -72.00   0.50    0.80    --  -96.00 -78.00 107.06   58
 65  ω   -103.00 -77.00   0.50    0.80    -- -100.00 -77.00 150.00   52
 66  ω   -108.00 -64.00   0.50    0.80    --  -84.00 -73.00 157.65   88
 67  ω   -107.00 -75.00   0.50    0.80    -- -100.00 -82.00 100.01   64
 68  ω   -122.00 -31.00   0.50    0.15    --  -46.37 -19.00 150.00  182
 69  ω   -120.00 -32.00   0.50    0.15    --  -46.37 -38.00   0.00  176
 70  ω   -114.00 -83.00   0.50    0.80    -- -100.00 -61.00 -60.00   62
 71  ω   -116.00 -67.00   0.50    0.80    --  -88.00 -71.00 -34.56   98
 72  ω   -121.00 -22.00   0.50    0.15    --  -48.00 -82.00 -39.69  198
 73  ω   -128.00 -30.00   0.50    0.15    --  -56.00 -82.00 -46.08  196
 74  ω   -122.00 -82.00   0.50    0.80    -- -100.00 -61.00  23.90   80
 75  ω   -120.00 -78.00   0.50    0.80    -- -100.00 -72.00  15.17   84
 76  ω   -124.00 -78.00   0.50    0.80    -- -100.00 -77.00  60.00   92
 77  ω   -135.00 -84.00   0.50    0.80    -- -100.00 -59.00 140.49  102
 78  ω   -123.00 -79.00   0.50    0.80    -- -100.00 -71.00 165.77   88
 79  ω   -124.00 -76.00   0.50    0.80    -- -100.00 -77.00 120.00   96
 80  ω   -137.00 -39.00   0.50    0.15    --  -64.00 -80.00  13.86  196
 81  ω   -119.00 -76.00   0.50    0.80    -- -100.00 -77.00-150.00   86
 82  ω   -124.00 -82.00   0.50    0.80    -- -100.00 -66.00-120.17   84
 83  ω   -137.00 -43.00   0.50    0.15    --  -64.00 -71.00-149.14  188
 84  ω   -137.00 -43.00   0.50    0.15    --  -64.00 -70.00-137.06  188
 85  ω   -140.00 -48.00   0.50    0.15    --  -68.00 -67.00 -24.89  184
 86  ω   -137.00 -38.00   0.50    0.15    --  -64.00 -82.00 148.12  198
 87  ω   -140.00 -45.00   0.50    0.15    --  -68.00 -75.00 170.45  190
 88  ω   -140.00 -46.00   0.50    0.15    --  -68.00 -72.00  81.89  188
 89  ω   -153.00-109.00   0.50    0.80    --  -80.00 -73.00 -90.34   88
 90  ω   -140.00 -46.00   0.50    0.15    --  -68.00 -72.00-161.04  188
 91  ω   -150.00-124.00   0.50    0.80    -- -100.00 -74.00 -57.38   52
 92  ω   -150.00 -76.00   0.50    0.80    -- -100.00 -77.00-120.00  148
 93  ω   -144.00-118.00   0.50    0.80    -- -100.00 -61.00 -60.00   52
 94  ω   -161.00-120.00   0.50    0.80    --  -92.00 -74.00 -95.40   82
 95  ω   -173.00 -79.00   0.50    0.80    -- -100.00-113.00 -75.00  188
 96  ω   -168.00-139.00   0.50    0.80    --  -96.00 -83.00 -83.89   58
 97  ω   -168.00-142.00   0.50    0.80    -- -100.00 -67.00 -34.29   52
 98  ω   -171.00-127.00   0.50    0.80    -- -100.00 -61.00  23.90   88
 99  ω   -169.00-128.00   0.50    0.80    --  -96.00 -78.00 107.06   82
100  ω   -167.00-133.00   0.50    0.80    -- -100.00 -71.00 165.77   68
101  ω   -172.00-134.00   0.50    0.80    -- -100.00 -77.00 150.00   76
102  ω   -173.00-132.00   0.50    0.80    -- -100.00 -77.00  60.00   82
103  ω   -165.00-128.00   0.50    0.80    -- -100.00 -72.00  15.17   74
104  ω   -167.00-132.00   0.50    0.80    -- -100.00 -77.00   0.00   70
105  ω   -173.00-111.00   0.50    0.80    -- -100.00 -77.00 -30.00  124
106  ω   -172.00 -76.00   0.50    0.80    -- -100.00 -77.00-170.29  192
107  ω   -169.00-126.00   0.50    0.80    -- -100.00 -77.00-150.00   86
108  ω    -74.00 -48.00   0.50    0.80    -- -100.00 113.00  16.00   52
109  ω    -88.00 -10.00   0.50    0.15    --  -40.00 124.00 166.92  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0914583000
_diffrn_orient_matrix_UB_12      0.0069517000
_diffrn_orient_matrix_UB_13      0.1057683000
_diffrn_orient_matrix_UB_21      -0.2917869000
_diffrn_orient_matrix_UB_22      -0.0092536000
_diffrn_orient_matrix_UB_23      -0.0588050000
_diffrn_orient_matrix_UB_31      -0.0354198000
_diffrn_orient_matrix_UB_32      -0.1312015000
_diffrn_orient_matrix_UB_33      -0.0224633000
_diffrn_oxdiff_digest_frames     
;
01ac48a6521e0567a38b74f8508dc27abb00088b308
;
_diffrn_oxdiff_digest_hkl        
;
01c26b65f235adca3a3067f31984d328ae616a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                2977
_reflns_number_total             3245
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.044
_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)+(0.1184P)²+0.2529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1708
_refine_ls_wR_factor_ref         0.1751
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C23(H23A,H23B), C22(H22A,H22B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 N9(H9), C10(H10), C11(H11), C17(H17), C5(H5), C2(H2), C4(H4), C16(H16), C3(H3)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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
O14 O 0.9085(2) 0.88229(10) 0.55939(9) 0.0331(3) Uani 1 1 d . . . . .
N9 N 0.6805(3) 0.93848(12) 0.41794(11) 0.0307(3) Uani 1 1 d . . . . .
H9 H 0.797296 0.995543 0.419653 0.037 Uiso 1 1 calc R . . . .
N15 N 1.0916(3) 0.63003(12) 0.87885(11) 0.0319(3) Uani 1 1 d . . . . .
C8 C 0.7094(3) 0.87104(13) 0.48740(13) 0.0289(4) Uani 1 1 d . . . . .
C1 C 0.4375(3) 0.90294(14) 0.34405(13) 0.0300(4) Uani 1 1 d . . . . .
C6 C 0.2937(3) 0.80939(14) 0.36634(13) 0.0294(4) Uani 1 1 d . . . . .
C18 C 0.7315(3) 0.59951(13) 0.74595(13) 0.0289(4) Uani 1 1 d . . . . .
C19 C 0.9548(3) 0.67948(14) 0.80672(13) 0.0290(4) Uani 1 1 d . . . . .
C7 C 0.4580(3) 0.78610(14) 0.45905(13) 0.0294(4) Uani 1 1 d . . . . .
C10 C 0.3996(3) 0.70727(14) 0.51266(13) 0.0305(4) Uani 1 1 d . . . . .
H10 H 0.232022 0.661539 0.489744 0.037 Uiso 1 1 calc R . . . .
C12 C 0.5306(3) 0.61081(14) 0.65724(13) 0.0293(4) Uani 1 1 d . . . . .
C11 C 0.5784(3) 0.68975(14) 0.60206(13) 0.0306(4) Uani 1 1 d . . . . .
H11 H 0.743989 0.737057 0.624770 0.037 Uiso 1 1 calc R . . . .
C13 C 0.2727(3) 0.52731(14) 0.62860(13) 0.0320(4) Uani 1 1 d . . . . .
H13A H 0.296934 0.455140 0.586497 0.048 Uiso 1 1 calc GR . . . .
H13B H 0.134908 0.556406 0.588312 0.048 Uiso 1 1 calc GR . . . .
H13C H 0.222267 0.517228 0.692755 0.048 Uiso 1 1 calc GR . . . .
C17 C 0.7390(3) 0.50019(14) 0.78572(13) 0.0327(4) Uani 1 1 d . . . . .
H17 H 0.614138 0.433284 0.761416 0.039 Uiso 1 1 calc R . . . .
C20 C 1.0556(3) 0.79923(14) 0.80495(13) 0.0315(4) Uani 1 1 d . . . . .
H20A H 0.905257 0.838637 0.791354 0.038 Uiso 1 1 calc R . . . .
H20B H 1.149076 0.796842 0.747254 0.038 Uiso 1 1 calc R . . . .
C5 C 0.0433(3) 0.75891(15) 0.30246(13) 0.0327(4) Uani 1 1 d . . . . .
H5 H -0.053930 0.696897 0.316020 0.039 Uiso 1 1 calc R . . . .
C2 C 0.3363(3) 0.94721(15) 0.26017(14) 0.0336(4) Uani 1 1 d . . . . .
H2 H 0.433206 1.009062 0.246214 0.040 Uiso 1 1 calc R . . . .
C23 C 1.3230(4) 0.68665(16) 0.96477(14) 0.0373(4) Uani 1 1 d . . . . .
H23A H 1.451362 0.635013 0.970182 0.045 Uiso 1 1 calc R . . . .
H23B H 1.266878 0.705707 1.032111 0.045 Uiso 1 1 calc R . . . .
C4 C -0.0594(3) 0.80278(15) 0.21782(14) 0.0349(4) Uani 1 1 d . . . . .
H4 H -0.226299 0.769504 0.174308 0.042 Uiso 1 1 calc R . . . .
C16 C 0.9609(4) 0.52092(15) 0.86527(14) 0.0347(4) Uani 1 1 d . . . . .
H16 H 1.015415 0.469918 0.904121 0.042 Uiso 1 1 calc R . . . .
C22 C 1.4540(3) 0.79477(16) 0.94396(15) 0.0376(4) Uani 1 1 d . . . . .
H22A H 1.551668 0.774694 0.887978 0.045 Uiso 1 1 calc R . . . .
H22B H 1.580144 0.839805 1.008195 0.045 Uiso 1 1 calc R . . . .
C21 C 1.2440(3) 0.86535(14) 0.91044(14) 0.0342(4) Uani 1 1 d . . . . .
H21A H 1.331408 0.936684 0.902540 0.041 Uiso 1 1 calc R . . . .
H21B H 1.142307 0.883325 0.965371 0.041 Uiso 1 1 calc R . . . .
C3 C 0.0856(4) 0.89615(16) 0.19770(14) 0.0345(4) Uani 1 1 d . . . . .
H3 H 0.012691 0.924733 0.141289 0.041 Uiso 1 1 calc R . . . .


_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
O14 C8 1.234(2) . ?
N9 H9 0.8600 . ?
N9 C8 1.367(2) . ?
N9 C1 1.392(2) . ?
N15 C19 1.373(2) . ?
N15 C23 1.461(2) . ?
N15 C16 1.377(2) . ?
C8 C7 1.493(2) . ?
C1 C6 1.408(2) . ?
C1 C2 1.385(2) . ?
C6 C7 1.460(2) . ?
C6 C5 1.390(2) . ?
C18 C19 1.399(2) . ?
C18 C12 1.458(2) . ?
C18 C17 1.430(2) . ?
C19 C20 1.500(2) . ?
C7 C10 1.358(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.432(2) . ?
C12 C11 1.362(2) . ?
C12 C13 1.508(2) . ?
C11 H11 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C16 1.358(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.526(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.393(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C22 1.518(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.395(3) . ?
C16 H16 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C21 1.526(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C3 H3 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
C8 N9 H9 124.4 . . ?
C8 N9 C1 111.30(14) . . ?
C1 N9 H9 124.4 . . ?
C19 N15 C23 126.08(15) . . ?
C19 N15 C16 109.42(14) . . ?
C16 N15 C23 124.19(14) . . ?
O14 C8 N9 124.64(15) . . ?
O14 C8 C7 128.56(15) . . ?
N9 C8 C7 106.79(14) . . ?
N9 C1 C6 109.13(14) . . ?
C2 C1 N9 128.96(15) . . ?
C2 C1 C6 121.91(16) . . ?
C1 C6 C7 107.19(14) . . ?
C5 C6 C1 119.53(15) . . ?
C5 C6 C7 133.28(16) . . ?
C19 C18 C12 128.10(15) . . ?
C19 C18 C17 106.55(14) . . ?
C17 C18 C12 125.34(15) . . ?
N15 C19 C18 107.54(14) . . ?
N15 C19 C20 120.12(14) . . ?
C18 C19 C20 132.34(15) . . ?
C6 C7 C8 105.54(14) . . ?
C10 C7 C8 125.54(15) . . ?
C10 C7 C6 128.89(15) . . ?
C7 C10 H10 117.8 . . ?
C7 C10 C11 124.49(15) . . ?
C11 C10 H10 117.8 . . ?
C18 C12 C13 115.80(14) . . ?
C11 C12 C18 121.57(15) . . ?
C11 C12 C13 122.60(15) . . ?
C10 C11 H11 116.7 . . ?
C12 C11 C10 126.61(15) . . ?
C12 C11 H11 116.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C18 C17 H17 126.1 . . ?
C16 C17 C18 107.85(15) . . ?
C16 C17 H17 126.1 . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C19 C20 C21 111.54(14) . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C6 C5 H5 120.6 . . ?
C6 C5 C4 118.89(16) . . ?
C4 C5 H5 120.6 . . ?
C1 C2 H2 121.1 . . ?
C1 C2 C3 117.74(16) . . ?
C3 C2 H2 121.1 . . ?
N15 C23 H23A 109.5 . . ?
N15 C23 H23B 109.5 . . ?
N15 C23 C22 110.79(14) . . ?
H23A C23 H23B 108.1 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C5 C4 H4 119.7 . . ?
C5 C4 C3 120.63(16) . . ?
C3 C4 H4 119.7 . . ?
N15 C16 H16 125.7 . . ?
C17 C16 N15 108.64(15) . . ?
C17 C16 H16 125.7 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C23 C22 C21 110.53(14) . . ?
H22A C22 H22B 108.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C20 C21 H21A 109.6 . . ?
C20 C21 H21B 109.6 . . ?
C22 C21 C20 110.36(14) . . ?
C22 C21 H21A 109.6 . . ?
C22 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C2 C3 C4 121.31(16) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?

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
O14 C8 C7 C6 -178.62(16) . . . . ?
O14 C8 C7 C10 3.1(3) . . . . ?
N9 C8 C7 C6 2.11(17) . . . . ?
N9 C8 C7 C10 -176.15(15) . . . . ?
N9 C1 C6 C7 -0.10(18) . . . . ?
N9 C1 C6 C5 -179.88(14) . . . . ?
N9 C1 C2 C3 -179.70(15) . . . . ?
N15 C19 C20 C21 -20.7(2) . . . . ?
N15 C23 C22 C21 46.5(2) . . . . ?
C8 N9 C1 C6 1.54(19) . . . . ?
C8 N9 C1 C2 -178.72(16) . . . . ?
C8 C7 C10 C11 -3.5(3) . . . . ?
C1 N9 C8 O14 178.42(15) . . . . ?
C1 N9 C8 C7 -2.27(18) . . . . ?
C1 C6 C7 C8 -1.21(17) . . . . ?
C1 C6 C7 C10 176.97(17) . . . . ?
C1 C6 C5 C4 -0.2(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
C6 C7 C10 C11 178.69(15) . . . . ?
C6 C5 C4 C3 -0.3(3) . . . . ?
C18 C19 C20 C21 159.09(17) . . . . ?
C18 C12 C11 C10 178.68(15) . . . . ?
C18 C17 C16 N15 1.08(19) . . . . ?
C19 N15 C23 C22 -19.0(2) . . . . ?
C19 N15 C16 C17 -0.70(19) . . . . ?
C19 C18 C12 C11 19.6(3) . . . . ?
C19 C18 C12 C13 -162.46(16) . . . . ?
C19 C18 C17 C16 -1.05(19) . . . . ?
C19 C20 C21 C22 48.63(19) . . . . ?
C7 C6 C5 C4 -179.90(16) . . . . ?
C7 C10 C11 C12 -178.91(16) . . . . ?
C12 C18 C19 N15 -177.88(15) . . . . ?
C12 C18 C19 C20 2.3(3) . . . . ?
C12 C18 C17 C16 177.51(15) . . . . ?
C13 C12 C11 C10 0.9(3) . . . . ?
C17 C18 C19 N15 0.62(18) . . . . ?
C17 C18 C19 C20 -179.18(16) . . . . ?
C17 C18 C12 C11 -158.64(16) . . . . ?
C17 C18 C12 C13 19.3(2) . . . . ?
C5 C6 C7 C8 178.52(17) . . . . ?
C5 C6 C7 C10 -3.3(3) . . . . ?
C5 C4 C3 C2 0.7(3) . . . . ?
C2 C1 C6 C7 -179.86(15) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C23 N15 C19 C18 -173.77(15) . . . . ?
C23 N15 C19 C20 6.1(2) . . . . ?
C23 N15 C16 C17 173.24(15) . . . . ?
C23 C22 C21 C20 -63.41(19) . . . . ?
C16 N15 C19 C18 0.03(18) . . . . ?
C16 N15 C19 C20 179.86(14) . . . . ?
C16 N15 C23 C22 168.06(15) . . . . ?

_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 1.399
_oxdiff_exptl_absorpt_empirical_full_min 0.674
####################################################################### 
# 
# 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_zhuzf_190904_2
_database_code_depnum_ccdc_archive 'CCDC 1965918'
loop_
_audit_author_name
_audit_author_address
'Zefeng Zhu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N O2'
_chemical_formula_sum            'C20 H19 N O2'
_chemical_formula_weight         305.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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/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                   7.4864(3)
_cell_length_b                   15.2133(8)
_cell_length_c                   13.6983(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.229(4)
_cell_angle_gamma                90
_cell_volume                     1557.66(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3347
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.8680
_cell_measurement_theta_min      4.3500
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9744
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.911
_diffrn_reflns_theta_min         4.347
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00 -13.00   0.50    0.50    --  -46.37  69.00  55.00   88
  2  ω     26.00 113.00   0.50    0.50    --   46.37  69.00  55.00  174
  3  ω    -21.00  67.00   0.50    0.50    --   46.37 -69.00 -77.00  176
  4  ω   -160.00 -79.00   0.50    1.00    -- -100.00 -69.00 -77.00  162
  5  ω   -119.00 -27.00   0.50    1.00    -- -100.00  69.00  55.00  184
  6  ω    137.00 170.00   0.50    1.00    --  105.44  69.00  55.00   66
  7  ω     64.00  89.00   0.50    1.00    --  105.44 -69.00 -77.00   50
  8  ω   -117.00 -78.00   0.50    0.50    --  -46.37-125.00  60.00   78
  9  ω   -118.00 -93.00   0.50    0.50    --  -46.37-125.00  30.00   50
 10  ω   -114.00 -81.00   0.50    1.00    -- -100.00 -94.00   0.00   66
 11  ω   -115.00 -27.00   0.50    1.00    -- -100.00  30.00 -90.00  176
 12  ω   -172.00-136.00   0.50    1.00    -- -100.00 -45.00   0.00   72
 13  ω   -130.00 -87.00   0.50    1.00    -- -100.00 -45.00   0.00   86
 14  ω   -157.00-131.00   0.50    1.00    -- -100.00 -94.00   0.00   52
 15  ω    143.00 178.00   0.50    1.00    --  105.44  45.00 150.00   70
 16  ω     91.00 173.00   0.50    1.00    --  105.44  45.00  90.00  164
 17  ω     38.00  98.00   0.50    1.00    --  105.44 -94.00 120.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0165550000
_diffrn_orient_matrix_UB_12      -0.0781281000
_diffrn_orient_matrix_UB_13      0.0704571000
_diffrn_orient_matrix_UB_21      0.1950885000
_diffrn_orient_matrix_UB_22      0.0140820000
_diffrn_orient_matrix_UB_23      0.0388064000
_diffrn_orient_matrix_UB_31      -0.0646280000
_diffrn_orient_matrix_UB_32      0.0627940000
_diffrn_orient_matrix_UB_33      0.0788713000
_diffrn_oxdiff_digest_frames     
;
010b3dc8e8aaa6d879f586cc111796d3f30004381b4
;
_diffrn_oxdiff_digest_hkl        
;
01bebf556e2d29e0634ea7d2577ac328dab890
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                2548
_reflns_number_total             3071
_reflns_odcompleteness_completeness 99.83
_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 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.056
_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)+(0.1136P)²+0.2594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1724
_refine_ls_wR_factor_ref         0.1847
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C16(H16), C10(H10), C5(H5), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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
O14 O 0.75285(19) 0.40132(10) 0.55114(10) 0.0460(4) Uani 1 1 d . . . . .
O9 O 0.6907(2) 0.31746(10) 0.41833(10) 0.0456(4) Uani 1 1 d . . . . .
N23 N 0.4723(2) 0.61977(11) 0.91319(12) 0.0385(4) Uani 1 1 d . . . . .
C18 C 0.4891(2) 0.56002(12) 0.83968(13) 0.0344(4) Uani 1 1 d . . . . .
C19 C 0.6660(2) 0.51589(12) 0.82799(13) 0.0353(4) Uani 1 1 d . . . . .
H19A H 0.722186 0.541648 0.772663 0.042 Uiso 1 1 calc R . . . .
H19B H 0.645849 0.454069 0.813934 0.042 Uiso 1 1 calc R . . . .
C8 C 0.6398(3) 0.36842(13) 0.49746(14) 0.0402(5) Uani 1 1 d . . . . .
C17 C 0.3259(2) 0.55491(13) 0.78637(14) 0.0380(4) Uani 1 1 d . . . . .
C11 C 0.3927(3) 0.45995(13) 0.64442(14) 0.0382(5) Uani 1 1 d . . . . .
H11 H 0.514238 0.464449 0.661864 0.046 Uiso 1 1 calc R . . . .
C7 C 0.4433(3) 0.36905(13) 0.49544(14) 0.0396(5) Uani 1 1 d . . . . .
C12 C 0.2748(2) 0.50220(13) 0.70060(15) 0.0402(5) Uani 1 1 d . . . . .
C6 C 0.3830(3) 0.31754(13) 0.41087(14) 0.0425(5) Uani 1 1 d . . . . .
C20 C 0.7924(3) 0.52444(14) 0.91894(14) 0.0400(5) Uani 1 1 d . . . . .
H20A H 0.754967 0.484490 0.969055 0.048 Uiso 1 1 calc R . . . .
H20B H 0.912587 0.508205 0.902874 0.048 Uiso 1 1 calc R . . . .
C1 C 0.5368(3) 0.28745(13) 0.36831(15) 0.0451(5) Uani 1 1 d . . . . .
C21 C 0.7931(3) 0.61799(15) 0.95794(15) 0.0421(5) Uani 1 1 d . . . . .
H21A H 0.826443 0.658432 0.907328 0.051 Uiso 1 1 calc R . . . .
H21B H 0.880143 0.623261 1.012825 0.051 Uiso 1 1 calc R . . . .
C15 C 0.3010(3) 0.65344(14) 0.90758(17) 0.0458(5) Uani 1 1 d . . . . .
H15 H 0.256652 0.695510 0.949101 0.055 Uiso 1 1 calc R . . . .
C16 C 0.2087(3) 0.61499(14) 0.83160(17) 0.0459(5) Uani 1 1 d . . . . .
H16 H 0.089735 0.625662 0.812031 0.055 Uiso 1 1 calc R . . . .
C10 C 0.3392(3) 0.40945(13) 0.56066(14) 0.0416(5) Uani 1 1 d . . . . .
H10 H 0.216391 0.403030 0.548598 0.050 Uiso 1 1 calc R . . . .
C22 C 0.6079(3) 0.64095(16) 0.99035(16) 0.0462(5) Uani 1 1 d . . . . .
H22A H 0.584328 0.608250 1.049041 0.055 Uiso 1 1 calc R . . . .
H22B H 0.602602 0.703147 1.005530 0.055 Uiso 1 1 calc R . . . .
C5 C 0.2161(3) 0.29340(15) 0.36985(16) 0.0511(6) Uani 1 1 d . . . . .
H5 H 0.111861 0.312893 0.396767 0.061 Uiso 1 1 calc R . . . .
C2 C 0.5322(4) 0.23343(15) 0.28773(16) 0.0550(6) Uani 1 1 d . . . . .
H2 H 0.636273 0.213362 0.261178 0.066 Uiso 1 1 calc R . . . .
C13 C 0.0758(3) 0.50055(18) 0.6756(2) 0.0606(6) Uani 1 1 d . . . . .
H13A H 0.014128 0.484388 0.732520 0.091 Uiso 1 1 calc GR . . . .
H13B H 0.049740 0.458432 0.624581 0.091 Uiso 1 1 calc GR . . . .
H13C H 0.036873 0.557761 0.653829 0.091 Uiso 1 1 calc GR . . . .
C3 C 0.3636(4) 0.21040(15) 0.24804(17) 0.0612(7) Uani 1 1 d . . . . .
H3 H 0.354835 0.174358 0.193146 0.073 Uiso 1 1 calc R . . . .
C4 C 0.2082(4) 0.23969(15) 0.28805(17) 0.0589(7) Uani 1 1 d . . . . .
H4 H 0.097556 0.223095 0.259652 0.071 Uiso 1 1 calc R . . . .


_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
O14 C8 1.199(2) . ?
O9 C8 1.403(3) . ?
O9 C1 1.384(3) . ?
N23 C18 1.368(2) . ?
N23 C15 1.379(3) . ?
N23 C22 1.460(3) . ?
C18 C19 1.501(2) . ?
C18 C17 1.390(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.527(3) . ?
C8 C7 1.470(3) . ?
C17 C12 1.456(3) . ?
C17 C16 1.432(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.364(3) . ?
C11 C10 1.420(3) . ?
C7 C6 1.449(3) . ?
C7 C10 1.365(3) . ?
C12 C13 1.510(3) . ?
C6 C1 1.397(3) . ?
C6 C5 1.391(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.520(3) . ?
C1 C2 1.375(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.520(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.350(3) . ?
C16 H16 0.9300 . ?
C10 H10 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.385(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.387(4) . ?
C4 H4 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
C1 O9 C8 108.04(16) . . ?
C18 N23 C15 109.25(17) . . ?
C18 N23 C22 126.22(16) . . ?
C15 N23 C22 124.39(17) . . ?
N23 C18 C19 119.61(16) . . ?
N23 C18 C17 108.02(16) . . ?
C17 C18 C19 132.34(17) . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C18 C19 C20 112.63(15) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
O14 C8 O9 119.44(19) . . ?
O14 C8 C7 132.8(2) . . ?
O9 C8 C7 107.72(16) . . ?
C18 C17 C12 129.66(17) . . ?
C18 C17 C16 106.20(18) . . ?
C16 C17 C12 124.13(18) . . ?
C12 C11 H11 118.4 . . ?
C12 C11 C10 123.27(18) . . ?
C10 C11 H11 118.4 . . ?
C6 C7 C8 106.12(18) . . ?
C10 C7 C8 126.78(18) . . ?
C10 C7 C6 127.10(19) . . ?
C17 C12 C13 113.79(19) . . ?
C11 C12 C17 124.45(17) . . ?
C11 C12 C13 121.7(2) . . ?
C1 C6 C7 106.50(18) . . ?
C5 C6 C7 134.3(2) . . ?
C5 C6 C1 119.2(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 C19 110.86(16) . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
O9 C1 C6 111.60(18) . . ?
C2 C1 O9 125.2(2) . . ?
C2 C1 C6 123.1(2) . . ?
C20 C21 H21A 109.8 . . ?
C20 C21 H21B 109.8 . . ?
C20 C21 C22 109.43(17) . . ?
H21A C21 H21B 108.2 . . ?
C22 C21 H21A 109.8 . . ?
C22 C21 H21B 109.8 . . ?
N23 C15 H15 125.8 . . ?
C16 C15 N23 108.43(18) . . ?
C16 C15 H15 125.8 . . ?
C17 C16 H16 125.9 . . ?
C15 C16 C17 108.10(18) . . ?
C15 C16 H16 125.9 . . ?
C11 C10 H10 115.6 . . ?
C7 C10 C11 128.85(19) . . ?
C7 C10 H10 115.6 . . ?
N23 C22 C21 110.26(16) . . ?
N23 C22 H22A 109.6 . . ?
N23 C22 H22B 109.6 . . ?
C21 C22 H22A 109.6 . . ?
C21 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C6 C5 H5 120.7 . . ?
C4 C5 C6 118.6(2) . . ?
C4 C5 H5 120.7 . . ?
C1 C2 H2 121.8 . . ?
C1 C2 C3 116.5(3) . . ?
C3 C2 H2 121.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?

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
O14 C8 C7 C6 179.3(2) . . . . ?
O14 C8 C7 C10 -1.2(4) . . . . ?
O9 C8 C7 C6 -0.9(2) . . . . ?
O9 C8 C7 C10 178.56(18) . . . . ?
O9 C1 C2 C3 179.83(19) . . . . ?
N23 C18 C19 C20 16.6(2) . . . . ?
N23 C18 C17 C12 179.10(18) . . . . ?
N23 C18 C17 C16 0.0(2) . . . . ?
N23 C15 C16 C17 -0.5(2) . . . . ?
C18 N23 C15 C16 0.5(2) . . . . ?
C18 N23 C22 C21 23.2(3) . . . . ?
C18 C19 C20 C21 -45.2(2) . . . . ?
C18 C17 C12 C11 -14.0(3) . . . . ?
C18 C17 C12 C13 168.2(2) . . . . ?
C18 C17 C16 C15 0.3(2) . . . . ?
C19 C18 C17 C12 1.0(3) . . . . ?
C19 C18 C17 C16 -178.1(2) . . . . ?
C19 C20 C21 C22 63.4(2) . . . . ?
C8 O9 C1 C6 0.6(2) . . . . ?
C8 O9 C1 C2 -178.24(19) . . . . ?
C8 C7 C6 C1 1.3(2) . . . . ?
C8 C7 C6 C5 179.7(2) . . . . ?
C8 C7 C10 C11 0.2(3) . . . . ?
C17 C18 C19 C20 -165.46(19) . . . . ?
C7 C6 C1 O9 -1.2(2) . . . . ?
C7 C6 C1 C2 177.67(18) . . . . ?
C7 C6 C5 C4 -177.9(2) . . . . ?
C12 C17 C16 C15 -178.86(18) . . . . ?
C12 C11 C10 C7 175.41(19) . . . . ?
C6 C7 C10 C11 179.65(19) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
C6 C5 C4 C3 0.2(3) . . . . ?
C20 C21 C22 N23 -50.3(2) . . . . ?
C1 O9 C8 O14 -179.95(17) . . . . ?
C1 O9 C8 C7 0.2(2) . . . . ?
C1 C6 C5 C4 0.3(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C15 N23 C18 C19 178.07(17) . . . . ?
C15 N23 C18 C17 -0.3(2) . . . . ?
C15 N23 C22 C21 -161.49(19) . . . . ?
C16 C17 C12 C11 164.94(19) . . . . ?
C16 C17 C12 C13 -12.9(3) . . . . ?
C10 C11 C12 C17 -179.53(18) . . . . ?
C10 C11 C12 C13 -1.9(3) . . . . ?
C10 C7 C6 C1 -178.20(19) . . . . ?
C10 C7 C6 C5 0.2(4) . . . . ?
C22 N23 C18 C19 -6.0(3) . . . . ?
C22 N23 C18 C17 175.59(18) . . . . ?
C22 N23 C15 C16 -175.49(19) . . . . ?
C5 C6 C1 O9 -179.89(17) . . . . ?
C5 C6 C1 C2 -1.0(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.038
_oxdiff_exptl_absorpt_empirical_full_min 0.533
####################################################################### 
# 
# 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_zhuzf_191011_3
_database_code_depnum_ccdc_archive 'CCDC 1965919'
loop_
_audit_author_name
_audit_author_address
'Zefeng Zhu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N2 O'
_chemical_formula_sum            'C20 H20 N2 O'
_chemical_formula_weight         304.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.4021(3)
_cell_length_b                   8.2439(3)
_cell_length_c                   20.2269(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.773(3)
_cell_angle_gamma                90
_cell_volume                     1562.35(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3086
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.2900
_cell_measurement_theta_min      4.3900
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.833
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9457
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.369
_diffrn_reflns_theta_min         4.387
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00  -8.00   0.50    0.30    --  -46.37 106.00 -91.00  146
  2  ω      5.00  43.00   0.50    0.30    --   46.37-106.00 169.00   76
  3  ω   -159.00 -82.00   0.50    1.00    -- -100.00-106.00 169.00  154
  4  ω   -108.00 -63.00   0.50    1.00    -- -100.00 106.00 -91.00   90
  5  ω    111.00 173.00   0.50    1.00    --  105.44 106.00 -91.00  124
  6  ω     72.00  97.00   0.50    1.00    --  105.44-106.00 169.00   50
  7  ω   -118.00 -75.00   0.50    0.30    --  -46.37-125.00-120.00   86
  8  ω   -117.00 -71.00   0.50    0.30    --  -46.37-125.00 -30.00   92
  9  ω    -25.00  59.00   0.50    0.30    --   46.37 -38.00  60.00  168
 10  ω   -123.00 -29.00   0.50    1.00    -- -100.00  77.00  90.00  188
 11  ω   -119.00 -60.00   0.50    1.00    -- -100.00  77.00 -90.00  118
 12  ω    100.00 178.00   0.50    1.00    --  105.44  45.00-120.00  156
 13  ω    134.00 160.00   0.50    1.00    --  105.44  45.00-180.00   52
 14  ω     97.00 122.00   0.50    1.00    --  105.44  45.00-180.00   50
 15  ω     46.00  76.00   0.50    1.00    --  105.44 -94.00 -30.00   60
 16  ω    104.00 178.00   0.50    1.00    --  105.44  45.00   0.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0078932000
_diffrn_orient_matrix_UB_12      -0.1407952000
_diffrn_orient_matrix_UB_13      -0.0502307000
_diffrn_orient_matrix_UB_21      0.0714804000
_diffrn_orient_matrix_UB_22      -0.1134171000
_diffrn_orient_matrix_UB_23      0.0534579000
_diffrn_orient_matrix_UB_31      -0.1479623000
_diffrn_orient_matrix_UB_32      -0.0472978000
_diffrn_orient_matrix_UB_33      0.0213320000
_diffrn_oxdiff_digest_frames     
;
01b8e5e4208f997670b9ae3781cbdfcf0f00055bf7c
;
_diffrn_oxdiff_digest_hkl        
;
0197fe59d3336dabcc267d80851db4d1da4cd6
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                2477
_reflns_number_total             3077
_reflns_odcompleteness_completeness 99.97
_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 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0633
_refine_ls_restrained_S_all      1.036
_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)+(0.1113P)²+0.3491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1669
_refine_ls_wR_factor_ref         0.1787
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H20C)=Sof(H20D)=Sof(H23C)=Sof(H23D)=Sof(C21A)=Sof(H21C)=Sof(H21D)=
 Sof(C22A)=Sof(H22C)=Sof(H22D)=1-FVAR(1)
 Sof(H20A)=Sof(H20B)=Sof(H23A)=Sof(H23B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C21)=
 Sof(H21A)=Sof(H21B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C20(H20C,H20D), C23(H23A,H23B), C23(H23C,H23D), C22(H22A,
 H22B), C21(H21A,H21B), C21A(H21C,H21D), C22A(H22C,H22D)
3.b Aromatic/amide H refined with riding coordinates:
 N9(H9), C11(H11), C10(H10), C5(H5), C2(H2), C17(H17), C4(H4), C3(H3), C16(H16)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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
O14 O 0.05225(15) 0.9024(3) 0.42057(8) 0.0611(5) Uani 1 1 d . . . . .
N15 N 0.78210(16) 0.3445(2) 0.30749(8) 0.0377(4) Uani 1 1 d . . . . .
N9 N 0.17927(17) 0.9587(2) 0.52059(9) 0.0431(4) Uani 1 1 d . . . . .
H9 H 0.116396 1.017302 0.537882 0.052 Uiso 1 1 calc R . . . .
C19 C 0.6972(2) 0.4464(2) 0.33995(10) 0.0343(4) Uani 1 1 d . . . . .
C1 C 0.31442(19) 0.9211(2) 0.55169(10) 0.0361(4) Uani 1 1 d . . . . .
C6 C 0.38863(19) 0.8230(2) 0.50947(10) 0.0353(4) Uani 1 1 d . . . . .
C11 C 0.4252(2) 0.6249(2) 0.37413(10) 0.0380(5) Uani 1 1 d . . . . .
H11 H 0.504217 0.622490 0.405006 0.046 Uiso 1 1 calc R . . . .
C10 C 0.30483(19) 0.7154(3) 0.39194(10) 0.0385(5) Uani 1 1 d . . . . .
H10 H 0.225935 0.718204 0.361011 0.046 Uiso 1 1 calc R . . . .
C5 C 0.5270(2) 0.7750(2) 0.53092(10) 0.0373(4) Uani 1 1 d . . . . .
H5 H 0.579403 0.710655 0.504031 0.045 Uiso 1 1 calc R . . . .
C18 C 0.56444(19) 0.4536(2) 0.30247(10) 0.0353(4) Uani 1 1 d . . . . .
C12 C 0.43654(19) 0.5419(2) 0.31692(10) 0.0355(4) Uani 1 1 d . . . . .
C7 C 0.29361(19) 0.7975(3) 0.44915(10) 0.0389(5) Uani 1 1 d . . . . .
C2 C 0.3706(2) 0.9696(2) 0.61364(10) 0.0378(4) Uani 1 1 d . . . . .
H2 H 0.318204 1.032885 0.640934 0.045 Uiso 1 1 calc R . . . .
C17 C 0.5761(2) 0.3539(3) 0.24577(10) 0.0410(5) Uani 1 1 d . . . . .
H17 H 0.505385 0.336518 0.211571 0.049 Uiso 1 1 calc R . . . .
C4 C 0.5856(2) 0.8245(3) 0.59286(11) 0.0418(5) Uani 1 1 d . . . . .
H4 H 0.678072 0.793009 0.607218 0.050 Uiso 1 1 calc R . . . .
C8 C 0.1616(2) 0.8901(3) 0.45971(11) 0.0440(5) Uani 1 1 d . . . . .
C3 C 0.5092(2) 0.9198(3) 0.63368(10) 0.0405(5) Uani 1 1 d . . . . .
H3 H 0.550829 0.951093 0.675039 0.049 Uiso 1 1 calc R . . . .
C20 C 0.7563(2) 0.5318(3) 0.40170(11) 0.0426(5) Uani 1 1 d . . . . .
H20A H 0.729529 0.473528 0.440443 0.051 Uiso 0.662(9) 1 calc R . P A 1
H20B H 0.716774 0.640366 0.402842 0.051 Uiso 0.662(9) 1 calc R . P A 1
H20C H 0.687133 0.526016 0.434643 0.051 Uiso 0.338(9) 1 calc R . P A 2
H20D H 0.770670 0.645333 0.391577 0.051 Uiso 0.338(9) 1 calc R . P A 2
C16 C 0.7099(2) 0.2885(3) 0.25065(11) 0.0437(5) Uani 1 1 d . . . . .
H16 H 0.745914 0.217673 0.220363 0.052 Uiso 1 1 calc R . . . .
C13 C 0.3135(2) 0.5301(3) 0.26418(11) 0.0429(5) Uani 1 1 d . . . . .
H13A H 0.277076 0.421284 0.262654 0.064 Uiso 1 1 calc GR . . . .
H13B H 0.345946 0.557903 0.221858 0.064 Uiso 1 1 calc GR . . . .
H13C H 0.239360 0.603655 0.274495 0.064 Uiso 1 1 calc GR . . . .
C23 C 0.9326(2) 0.3069(3) 0.32686(12) 0.0453(5) Uani 1 1 d . . . . .
H23A H 0.990854 0.351342 0.293849 0.054 Uiso 0.662(9) 1 calc R . P A 1
H23B H 0.944972 0.190076 0.327097 0.054 Uiso 0.662(9) 1 calc R . P A 1
H23C H 0.986637 0.302356 0.288085 0.054 Uiso 0.338(9) 1 calc R . P A 2
H23D H 0.940953 0.203167 0.349485 0.054 Uiso 0.338(9) 1 calc R . P A 2
C22 C 0.9854(5) 0.3733(8) 0.3945(3) 0.0537(12) Uani 0.662(9) 1 d . . P A 1
H22A H 0.954964 0.302497 0.428946 0.064 Uiso 0.662(9) 1 calc R . P A 1
H22B H 1.088836 0.376955 0.398501 0.064 Uiso 0.662(9) 1 calc R . P A 1
C21 C 0.9263(4) 0.5416(6) 0.4030(2) 0.0511(14) Uani 0.662(9) 1 d . . P A 1
H21A H 0.953252 0.611425 0.367565 0.061 Uiso 0.662(9) 1 calc R . P A 1
H21B H 0.965352 0.587081 0.444923 0.061 Uiso 0.662(9) 1 calc R . P A 1
C21A C 0.8959(6) 0.4603(8) 0.4305(3) 0.0332(19) Uani 0.338(9) 1 d . . P A 2
H21C H 0.880209 0.355915 0.450860 0.040 Uiso 0.338(9) 1 calc R . P A 2
H21D H 0.941839 0.532023 0.463778 0.040 Uiso 0.338(9) 1 calc R . P A 2
C22A C 0.9869(7) 0.4413(11) 0.3724(5) 0.0402(19) Uani 0.338(9) 1 d . . P A 2
H22C H 0.986607 0.542257 0.347815 0.048 Uiso 0.338(9) 1 calc R . P A 2
H22D H 1.084597 0.418170 0.389034 0.048 Uiso 0.338(9) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O14 C8 1.248(3) . ?
N15 C19 1.364(3) . ?
N15 C16 1.366(3) . ?
N15 C23 1.469(3) . ?
N9 H9 0.8600 . ?
N9 C1 1.405(2) . ?
N9 C8 1.353(3) . ?
C19 C18 1.407(3) . ?
C19 C20 1.500(3) . ?
C1 C6 1.403(3) . ?
C1 C2 1.378(3) . ?
C6 C5 1.394(3) . ?
C6 C7 1.466(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.427(3) . ?
C11 C12 1.356(3) . ?
C10 H10 0.9300 . ?
C10 C7 1.352(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.387(3) . ?
C18 C12 1.456(3) . ?
C18 C17 1.423(3) . ?
C12 C13 1.510(3) . ?
C7 C8 1.488(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.365(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.384(3) . ?
C3 H3 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C20 H20D 0.9700 . ?
C20 C21 1.599(4) . ?
C20 C21A 1.511(5) . ?
C16 H16 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C23 H23D 0.9700 . ?
C23 C22 1.518(5) . ?
C23 C22A 1.503(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C21 1.510(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21A H21C 0.9700 . ?
C21A H21D 0.9700 . ?
C21A C22A 1.518(12) . ?
C22A H22C 0.9700 . ?
C22A H22D 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
C19 N15 C16 110.10(17) . . ?
C19 N15 C23 126.20(17) . . ?
C16 N15 C23 123.57(18) . . ?
C1 N9 H9 124.6 . . ?
C8 N9 H9 124.6 . . ?
C8 N9 C1 110.70(16) . . ?
N15 C19 C18 107.18(17) . . ?
N15 C19 C20 119.93(17) . . ?
C18 C19 C20 132.80(18) . . ?
C6 C1 N9 109.37(17) . . ?
C2 C1 N9 127.38(18) . . ?
C2 C1 C6 123.25(18) . . ?
C1 C6 C7 106.83(16) . . ?
C5 C6 C1 118.19(18) . . ?
C5 C6 C7 134.97(19) . . ?
C10 C11 H11 116.6 . . ?
C12 C11 H11 116.6 . . ?
C12 C11 C10 126.83(18) . . ?
C11 C10 H10 116.6 . . ?
C7 C10 C11 126.72(18) . . ?
C7 C10 H10 116.6 . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.22(19) . . ?
C4 C5 H5 120.4 . . ?
C19 C18 C12 128.59(18) . . ?
C19 C18 C17 106.58(17) . . ?
C17 C18 C12 124.83(17) . . ?
C11 C12 C18 123.25(17) . . ?
C11 C12 C13 121.71(18) . . ?
C18 C12 C13 115.01(17) . . ?
C6 C7 C8 105.36(17) . . ?
C10 C7 C6 134.29(18) . . ?
C10 C7 C8 120.35(18) . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.22(19) . . ?
C3 C2 H2 121.4 . . ?
C18 C17 H17 126.2 . . ?
C16 C17 C18 107.62(18) . . ?
C16 C17 H17 126.2 . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.24(18) . . ?
C3 C4 H4 119.4 . . ?
O14 C8 N9 125.16(19) . . ?
O14 C8 C7 127.1(2) . . ?
N9 C8 C7 107.73(17) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.87(19) . . ?
C4 C3 H3 119.6 . . ?
C19 C20 H20A 109.7 . . ?
C19 C20 H20B 109.7 . . ?
C19 C20 H20C 109.0 . . ?
C19 C20 H20D 109.0 . . ?
C19 C20 C21 109.8(2) . . ?
C19 C20 C21A 112.8(3) . . ?
H20A C20 H20B 108.2 . . ?
H20C C20 H20D 107.8 . . ?
C21 C20 H20A 109.7 . . ?
C21 C20 H20B 109.7 . . ?
C21A C20 H20C 109.0 . . ?
C21A C20 H20D 109.0 . . ?
N15 C16 H16 125.7 . . ?
C17 C16 N15 108.51(18) . . ?
C17 C16 H16 125.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N15 C23 H23A 108.9 . . ?
N15 C23 H23B 108.9 . . ?
N15 C23 H23C 110.5 . . ?
N15 C23 H23D 110.5 . . ?
N15 C23 C22 113.5(2) . . ?
N15 C23 C22A 106.2(3) . . ?
H23A C23 H23B 107.7 . . ?
H23C C23 H23D 108.7 . . ?
C22 C23 H23A 108.9 . . ?
C22 C23 H23B 108.9 . . ?
C22A C23 H23C 110.5 . . ?
C22A C23 H23D 110.5 . . ?
C23 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C21 C22 C23 109.8(4) . . ?
C21 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
C20 C21 H21A 109.8 . . ?
C20 C21 H21B 109.8 . . ?
C22 C21 C20 109.2(4) . . ?
C22 C21 H21A 109.8 . . ?
C22 C21 H21B 109.8 . . ?
H21A C21 H21B 108.3 . . ?
C20 C21A H21C 110.6 . . ?
C20 C21A H21D 110.6 . . ?
C20 C21A C22A 105.6(6) . . ?
H21C C21A H21D 108.7 . . ?
C22A C21A H21C 110.6 . . ?
C22A C21A H21D 110.6 . . ?
C23 C22A C21A 111.5(6) . . ?
C23 C22A H22C 109.3 . . ?
C23 C22A H22D 109.3 . . ?
C21A C22A H22C 109.3 . . ?
C21A C22A H22D 109.3 . . ?
H22C C22A H22D 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
N15 C19 C18 C12 178.12(18) . . . . ?
N15 C19 C18 C17 -1.1(2) . . . . ?
N15 C19 C20 C21 22.4(3) . . . . ?
N15 C19 C20 C21A -14.8(4) . . . . ?
N15 C23 C22 C21 -40.7(6) . . . . ?
N15 C23 C22A C21A 55.2(8) . . . . ?
N9 C1 C6 C5 178.70(17) . . . . ?
N9 C1 C6 C7 -0.5(2) . . . . ?
N9 C1 C2 C3 -178.66(19) . . . . ?
C19 N15 C16 C17 -0.1(2) . . . . ?
C19 N15 C23 C22 8.7(4) . . . . ?
C19 N15 C23 C22A -19.5(5) . . . . ?
C19 C18 C12 C11 -4.9(3) . . . . ?
C19 C18 C12 C13 177.15(19) . . . . ?
C19 C18 C17 C16 1.1(2) . . . . ?
C19 C20 C21 C22 -53.9(5) . . . . ?
C19 C20 C21A C22A 47.2(6) . . . . ?
C1 N9 C8 O14 179.9(2) . . . . ?
C1 N9 C8 C7 0.8(2) . . . . ?
C1 C6 C5 C4 0.5(3) . . . . ?
C1 C6 C7 C10 -179.9(2) . . . . ?
C1 C6 C7 C8 0.9(2) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C6 C5 C4 C3 0.2(3) . . . . ?
C6 C7 C8 O14 179.8(2) . . . . ?
C6 C7 C8 N9 -1.1(2) . . . . ?
C11 C10 C7 C6 -0.6(4) . . . . ?
C11 C10 C7 C8 178.4(2) . . . . ?
C10 C11 C12 C18 179.39(19) . . . . ?
C10 C11 C12 C13 -2.8(3) . . . . ?
C10 C7 C8 O14 0.5(4) . . . . ?
C10 C7 C8 N9 179.7(2) . . . . ?
C5 C6 C7 C10 1.1(4) . . . . ?
C5 C6 C7 C8 -178.1(2) . . . . ?
C5 C4 C3 C2 -0.2(3) . . . . ?
C18 C19 C20 C21 -153.5(3) . . . . ?
C18 C19 C20 C21A 169.3(4) . . . . ?
C18 C17 C16 N15 -0.6(2) . . . . ?
C12 C11 C10 C7 179.7(2) . . . . ?
C12 C18 C17 C16 -178.22(19) . . . . ?
C7 C6 C5 C4 179.3(2) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
C2 C1 C6 C7 179.56(19) . . . . ?
C17 C18 C12 C11 174.26(19) . . . . ?
C17 C18 C12 C13 -3.7(3) . . . . ?
C8 N9 C1 C6 -0.2(2) . . . . ?
C8 N9 C1 C2 179.8(2) . . . . ?
C20 C19 C18 C12 -5.6(4) . . . . ?
C20 C19 C18 C17 175.2(2) . . . . ?
C20 C21A C22A C23 -71.3(8) . . . . ?
C16 N15 C19 C18 0.8(2) . . . . ?
C16 N15 C19 C20 -176.07(18) . . . . ?
C16 N15 C23 C22 -175.8(4) . . . . ?
C16 N15 C23 C22A 156.0(5) . . . . ?
C23 N15 C19 C18 176.76(18) . . . . ?
C23 N15 C19 C20 -0.1(3) . . . . ?
C23 N15 C16 C17 -176.21(19) . . . . ?
C23 C22 C21 C20 63.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.492
_oxdiff_exptl_absorpt_empirical_full_min 0.660
