# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_ytt-229
_audit_block_doi                 10.5517/ccdc.csd.cc2d5dbb
_database_code_depnum_ccdc_archive 'CCDC 2209721'
loop_
_audit_author_name
_audit_author_address
ytt
;Jinan University
China
;
_audit_update_record             
;
2022-10-08 deposited with the CCDC.	2023-08-06 downloaded from the CCDC.
;
_audit_creation_date             2022-08-17
_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         'Cl, C19 H21 N2 O2'
_chemical_formula_sum            'C19 H21 Cl N2 O2'
_chemical_formula_weight         344.83
_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'
Cl Cl 0.3639 0.7018 '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                   8.3746(2)
_cell_length_b                   10.1900(3)
_cell_length_c                   20.3391(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.588(3)
_cell_angle_gamma                90
_cell_volume                     1735.01(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6380
_cell_measurement_temperature    170.0(2)
_cell_measurement_theta_max      73.7580
_cell_measurement_theta_min      2.1670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.056
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46243
_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    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11119
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.121
_diffrn_reflns_theta_min         4.349
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.0(2)
_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 0.974
_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  29.00   1.00    1.00    --  -40.73  38.00   0.00   83
  2  ω    -77.00 -13.00   1.00    1.00    --  -40.73 -57.00-150.00   64
  3  ω   -113.00 -14.00   1.00    1.00    --  -40.73 -57.00  30.00   99
  4  ω    129.00 175.00   1.00    1.00    --  107.58 125.00-120.00   46
  5  ω     79.00 177.00   1.00    1.00    --  107.58  30.00-180.00   98
  6  ω     53.00 106.00   1.00    1.00    --  107.58 -94.00-120.00   53
  7  ω     36.00 128.00   1.00    1.00    --  107.58 -77.00 -60.00   92
  8  ω     81.00 169.00   1.00    1.00    --  107.58  30.00  90.00   88
  9  ω     56.00  86.00   1.00    1.00    --  107.58-125.00 120.00   30
 10  ω    -69.00 -31.00   1.00    1.00    --  -40.98 -57.00 150.00   38
 11  ω    -68.00 -16.00   1.00    1.00    --  -40.98 -57.00  90.00   52
 12  ω     23.00  69.00   1.00    1.00    --   40.98-125.00 120.00   46
 13  ω     94.00 120.00   1.00    1.00    --   40.98  19.00 -90.00   26
 14  ω     50.00  76.00   1.00    1.00    --   40.98  38.00 -60.00   26
 15  ω     53.00  85.00   1.00    1.00    --   40.98-125.00   0.00   32
 16  ω     18.00  58.00   1.00    1.00    --   40.98  77.00-120.00   40
 17  ω     26.00  53.00   1.00    1.00    --   40.98  19.00 -90.00   27
 18  ω    153.00 178.00   1.00    1.00    --  107.58  77.00 -90.00   25
 19  ω     83.00 109.00   1.00    1.00    --  107.58  45.00-120.00   26
 20  ω     79.00 105.00   1.00    1.00    --  107.58  61.00 -90.00   26
 21  ω     76.00 102.00   1.00    1.00    --  107.58  77.00-180.00   26
 22  ω     78.00 104.00   1.00    1.00    --  107.58  61.00 -60.00   26
 23  ω     75.00 101.00   1.00    1.00    --  107.58  77.00-150.00   26
 24  ω     75.00 100.00   1.00    1.00    --  107.58  77.00 -90.00   25
 25  ω     78.00 104.00   1.00    1.00    --  107.58  61.00-120.00   26
 26  ω     82.00 108.00   1.00    1.00    --  107.58  45.00-150.00   26
 27  ω     75.00  92.00   1.00    1.00    --  107.58  77.00 150.00   17
;
_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      0.1252433000
_diffrn_orient_matrix_UB_12      -0.0211469000
_diffrn_orient_matrix_UB_13      -0.0530222000
_diffrn_orient_matrix_UB_21      -0.1344351000
_diffrn_orient_matrix_UB_22      -0.0304780000
_diffrn_orient_matrix_UB_23      -0.0510274000
_diffrn_orient_matrix_UB_31      -0.0098420000
_diffrn_orient_matrix_UB_32      0.1465249000
_diffrn_orient_matrix_UB_33      -0.0181965000
_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                3091
_reflns_number_total             3446
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.061
_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+1.1528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1394
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.38005(7) 0.15120(5) 0.46756(3) 0.04171(19) Uani 1 1 d . . . . .
O1 O 0.91027(17) 0.15140(15) 0.64699(7) 0.0338(4) Uani 1 1 d . . . . .
O2 O 1.1428(2) 0.44750(15) 0.42292(8) 0.0390(4) Uani 1 1 d . . . . .
N1 N 0.9127(2) 0.09868(19) 0.71212(8) 0.0342(4) Uani 1 1 d . . . . .
N2 N 0.7797(2) 0.08943(18) 0.48137(9) 0.0313(4) Uani 1 1 d . . . . .
H2 H 0.715(4) 0.038(3) 0.5000(15) 0.055(9) Uiso 1 1 d . . . . .
C1 C 0.7420(2) 0.0549(2) 0.80139(9) 0.0279(4) Uani 1 1 d . . . . .
C2 C 0.6338(3) 0.1137(2) 0.84326(10) 0.0314(4) Uani 1 1 d . . . . .
H2A H 0.579002 0.191174 0.829760 0.038 Uiso 1 1 calc R U . . .
C3 C 0.6056(3) 0.0594(2) 0.90466(10) 0.0364(5) Uani 1 1 d . . . . .
H3 H 0.531792 0.100144 0.932847 0.044 Uiso 1 1 calc R U . . .
C4 C 0.6845(3) -0.0533(2) 0.92486(10) 0.0383(5) Uani 1 1 d . . . . .
H4 H 0.664604 -0.090381 0.966701 0.046 Uiso 1 1 calc R U . . .
C5 C 0.7924(3) -0.1119(2) 0.88389(11) 0.0379(5) Uani 1 1 d . . . . .
H5 H 0.846825 -0.189359 0.897746 0.045 Uiso 1 1 calc R U . . .
C6 C 0.8220(3) -0.0585(2) 0.82263(10) 0.0331(5) Uani 1 1 d . . . . .
H6 H 0.896999 -0.099178 0.794991 0.040 Uiso 1 1 calc R U . . .
C7 C 0.7734(2) 0.10886(19) 0.73547(9) 0.0266(4) Uani 1 1 d . . . . .
C8 C 0.6540(2) 0.1776(2) 0.68889(10) 0.0295(4) Uani 1 1 d . . . . .
C9 C 0.7441(2) 0.1503(2) 0.62583(10) 0.0305(4) Uani 1 1 d . . . . .
H9 H 0.716197 0.059775 0.610338 0.037 Uiso 1 1 calc R U . . .
C10 C 0.7175(3) 0.2442(2) 0.56907(10) 0.0306(4) Uani 1 1 d . . . . .
H10A H 0.602153 0.246900 0.557184 0.037 Uiso 1 1 calc R U . . .
H10B H 0.750146 0.333460 0.583263 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8089(2) 0.20693(19) 0.50945(9) 0.0272(4) Uani 1 1 d . . . . .
C12 C 0.9193(2) 0.28889(19) 0.48133(9) 0.0263(4) Uani 1 1 d . . . . .
H12 H 0.942847 0.371668 0.500783 0.032 Uiso 1 1 calc R U . . .
C13 C 0.9959(2) 0.25094(19) 0.42491(9) 0.0268(4) Uani 1 1 d . . . . .
C14 C 0.9595(3) 0.1301(2) 0.39647(10) 0.0324(5) Uani 1 1 d . . . . .
H14 H 1.008041 0.103422 0.356979 0.039 Uiso 1 1 calc R U . . .
C15 C 0.8515(3) 0.0499(2) 0.42677(11) 0.0352(5) Uani 1 1 d . . . . .
H15 H 0.827743 -0.034150 0.408815 0.042 Uiso 1 1 calc R U . . .
C16 C 1.1156(2) 0.34417(19) 0.39548(10) 0.0292(4) Uani 1 1 d . . . . .
C17 C 1.1920(3) 0.3074(2) 0.33280(11) 0.0378(5) Uani 1 1 d . . . . .
H17A H 1.274215 0.372167 0.322593 0.057 Uiso 1 1 calc R U . . .
H17B H 1.110907 0.305485 0.297132 0.057 Uiso 1 1 calc R U . . .
H17C H 1.241069 0.220520 0.337460 0.057 Uiso 1 1 calc R U . . .
C18 C 0.6450(3) 0.3231(2) 0.70629(12) 0.0438(6) Uani 1 1 d . . . . .
H18A H 0.602236 0.332951 0.750381 0.066 Uiso 1 1 calc R U . . .
H18B H 0.574843 0.368150 0.674221 0.066 Uiso 1 1 calc R U . . .
H18C H 0.752184 0.361539 0.705436 0.066 Uiso 1 1 calc R U . . .
C19 C 0.4891(3) 0.1149(3) 0.68421(12) 0.0426(6) Uani 1 1 d . . . . .
H19A H 0.499688 0.021548 0.673519 0.064 Uiso 1 1 calc R U . . .
H19B H 0.424805 0.158564 0.649670 0.064 Uiso 1 1 calc R U . . .
H19C H 0.436527 0.124106 0.726417 0.064 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 N1 1.429(2) . ?
O1 C9 1.446(2) . ?
O2 C16 1.211(2) . ?
N1 C7 1.277(3) . ?
N2 H2 0.85(3) . ?
N2 C11 1.346(3) . ?
N2 C15 1.339(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.398(3) . ?
C1 C7 1.480(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.392(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.528(3) . ?
C8 C9 1.531(3) . ?
C8 C18 1.527(3) . ?
C8 C19 1.522(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.512(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.501(3) . ?
C11 C12 1.382(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(3) . ?
C13 C14 1.391(3) . ?
C13 C16 1.516(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.490(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 C9 105.19(14) . . ?
C7 N1 O1 108.93(16) . . ?
C11 N2 H2 118(2) . . ?
C15 N2 H2 119(2) . . ?
C15 N2 C11 122.59(19) . . ?
C2 C1 C6 118.68(19) . . ?
C2 C1 C7 121.87(18) . . ?
C6 C1 C7 119.45(18) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2A 119.8 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C1 119.62(18) . . ?
N1 C7 C8 113.32(17) . . ?
C1 C7 C8 127.05(17) . . ?
C7 C8 C9 96.14(15) . . ?
C18 C8 C7 109.68(18) . . ?
C18 C8 C9 113.52(18) . . ?
C19 C8 C7 115.05(18) . . ?
C19 C8 C9 109.78(18) . . ?
C19 C8 C18 111.8(2) . . ?
O1 C9 C8 104.00(15) . . ?
O1 C9 H9 108.4 . . ?
O1 C9 C10 110.01(17) . . ?
C8 C9 H9 108.4 . . ?
C10 C9 C8 117.34(17) . . ?
C10 C9 H9 108.4 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 C9 112.92(17) . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
N2 C11 C10 118.52(18) . . ?
N2 C11 C12 118.55(18) . . ?
C12 C11 C10 122.92(18) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.31(18) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 119.38(19) . . ?
C12 C13 C16 118.58(18) . . ?
C14 C13 C16 122.03(18) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.58(19) . . ?
C15 C14 H14 120.7 . . ?
N2 C15 C14 120.54(19) . . ?
N2 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
O2 C16 C13 118.77(19) . . ?
O2 C16 C17 122.21(19) . . ?
C17 C16 C13 119.00(18) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C18 H18A 109.5 . . ?
C8 C18 H18B 109.5 . . ?
C8 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 N1 C7 C1 176.86(16) . . . . ?
O1 N1 C7 C8 -2.5(2) . . . . ?
O1 C9 C10 C11 62.6(2) . . . . ?
N1 O1 C9 C8 33.96(19) . . . . ?
N1 O1 C9 C10 160.44(16) . . . . ?
N1 C7 C8 C9 22.2(2) . . . . ?
N1 C7 C8 C18 -95.5(2) . . . . ?
N1 C7 C8 C19 137.4(2) . . . . ?
N2 C11 C12 C13 1.0(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C7 C8 C9 -157.11(19) . . . . ?
C1 C7 C8 C18 85.2(2) . . . . ?
C1 C7 C8 C19 -41.9(3) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C2 C1 C7 N1 146.7(2) . . . . ?
C2 C1 C7 C8 -34.1(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C6 C1 C7 N1 -33.6(3) . . . . ?
C6 C1 C7 C8 145.7(2) . . . . ?
C7 C1 C2 C3 179.24(19) . . . . ?
C7 C1 C6 C5 -179.00(19) . . . . ?
C7 C8 C9 O1 -32.36(18) . . . . ?
C7 C8 C9 C10 -154.08(18) . . . . ?
C8 C9 C10 C11 -178.89(17) . . . . ?
C9 O1 N1 C7 -20.2(2) . . . . ?
C9 C10 C11 N2 60.0(2) . . . . ?
C9 C10 C11 C12 -121.3(2) . . . . ?
C10 C11 C12 C13 -177.70(18) . . . . ?
C11 N2 C15 C14 -0.4(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C11 C12 C13 C16 179.69(17) . . . . ?
C12 C13 C14 C15 -2.1(3) . . . . ?
C12 C13 C16 O2 1.5(3) . . . . ?
C12 C13 C16 C17 -176.71(18) . . . . ?
C13 C14 C15 N2 2.0(3) . . . . ?
C14 C13 C16 O2 -179.45(19) . . . . ?
C14 C13 C16 C17 2.3(3) . . . . ?
C15 N2 C11 C10 177.65(19) . . . . ?
C15 N2 C11 C12 -1.1(3) . . . . ?
C16 C13 C14 C15 178.89(19) . . . . ?
C18 C8 C9 O1 82.2(2) . . . . ?
C18 C8 C9 C10 -39.5(3) . . . . ?
C19 C8 C9 O1 -151.78(17) . . . . ?
C19 C8 C9 C10 86.5(2) . . . . ?

_olex2_date_sample_data_collection 2022-05-16
_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 1.845
_oxdiff_exptl_absorpt_empirical_full_min 0.438
####################################################################### 
# 
# 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_ytt-214
_audit_block_doi                 10.5517/ccdc.csd.cc2d57ys
_database_code_depnum_ccdc_archive 'CCDC 2209585'
loop_
_audit_author_name
_audit_author_address
heyutao
;Jinan University
China
;
_audit_update_record             
;
2022-09-26 deposited with the CCDC.	2023-08-06 downloaded from the CCDC.
;
_audit_creation_date             2022-07-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 N2 O'
_chemical_formula_sum            'C21 H20 N2 O'
_chemical_formula_weight         316.39
_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                   11.5609(2)
_cell_length_b                   11.2342(2)
_cell_length_c                   25.6255(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3328.18(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6651
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.7700
_cell_measurement_theta_min      5.1240
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67733
_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    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11839
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.903
_diffrn_reflns_theta_min         3.449
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(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 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00   0.00   1.00    1.00    --  -40.73 -19.00  30.00  121
  2  ω      1.00  82.00   1.00    1.00    --   40.73 -99.00 -90.00   81
  3  ω     35.00 113.00   1.00    2.05    --  107.58-125.00  30.00   78
  4  ω    135.00 178.00   1.00    2.05    --  107.58  45.00-120.00   43
  5  ω     96.00 177.00   1.00    2.05    --  107.58 125.00 150.00   81
  6  ω    125.00 151.00   1.00    2.05    --  107.58 107.00  80.00   26
  7  ω     98.00 173.00   1.00    2.05    --  107.58  45.00 150.00   75
  8  ω     88.00 114.00   1.00    2.05    --  107.58  45.00-120.00   26
  9  ω     35.00 135.00   1.00    2.05    --  107.58 -61.00  90.00  100
;
_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      -0.0709669000
_diffrn_orient_matrix_UB_12      0.0248849000
_diffrn_orient_matrix_UB_13      -0.0496984000
_diffrn_orient_matrix_UB_21      0.0754220000
_diffrn_orient_matrix_UB_22      -0.0893228000
_diffrn_orient_matrix_UB_23      -0.0304875000
_diffrn_orient_matrix_UB_31      -0.0837066000
_diffrn_orient_matrix_UB_32      -0.1011885000
_diffrn_orient_matrix_UB_33      0.0146308000
_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                3014
_reflns_number_total             3310
_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 1.171.38.43f (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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00083(10)
_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   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.019
_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)+(0.0492P)²+0.7722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0936
_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:
 C10(H10A,H10B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), 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 0.03120(6) 0.46250(7) 0.61453(3) 0.03018(19) Uani 1 1 d . . . . .
N1 N 0.41464(8) 0.43866(8) 0.58811(3) 0.0270(2) Uani 1 1 d . . . . .
C1 C 0.52850(9) 0.47210(10) 0.58553(4) 0.0265(2) Uani 1 1 d . . . . .
N2 N 0.01764(8) 0.35714(8) 0.64368(4) 0.0288(2) Uani 1 1 d . . . . .
C2 C 0.61194(10) 0.39385(11) 0.60709(5) 0.0328(3) Uani 1 1 d . . . . .
H2 H 0.588168 0.323316 0.622766 0.039 Uiso 1 1 calc R U . . .
C3 C 0.72713(10) 0.42120(12) 0.60504(5) 0.0368(3) Uani 1 1 d . . . . .
H3 H 0.781134 0.368837 0.619052 0.044 Uiso 1 1 calc R U . . .
C4 C 0.76443(10) 0.52801(12) 0.58187(5) 0.0367(3) Uani 1 1 d . . . . .
H4 H 0.842901 0.546037 0.580758 0.044 Uiso 1 1 calc R U . . .
C5 C 0.68580(10) 0.60547(11) 0.56096(4) 0.0319(3) Uani 1 1 d . . . . .
H5 H 0.711466 0.676099 0.545982 0.038 Uiso 1 1 calc R U . . .
C6 C 0.56586(9) 0.57975(9) 0.56179(4) 0.0259(2) Uani 1 1 d . . . . .
C7 C 0.48029(9) 0.65532(9) 0.53922(4) 0.0266(2) Uani 1 1 d . . . . .
C8 C 0.36734(9) 0.61936(10) 0.54260(4) 0.0270(2) Uani 1 1 d . . . . .
H8 H 0.309473 0.666981 0.528469 0.032 Uiso 1 1 calc R U . . .
C9 C 0.33717(9) 0.51084(9) 0.56727(4) 0.0255(2) Uani 1 1 d . . . . .
C10 C 0.21271(9) 0.47224(10) 0.57030(4) 0.0273(2) Uani 1 1 d . . . . .
H10A H 0.209527 0.386341 0.566736 0.033 Uiso 1 1 calc R U . . .
H10B H 0.171290 0.506351 0.540977 0.033 Uiso 1 1 calc R U . . .
C11 C 0.14988(9) 0.50755(10) 0.62091(4) 0.0260(2) Uani 1 1 d . . . . .
C12 C 0.19463(9) 0.43990(10) 0.66859(4) 0.0275(2) Uani 1 1 d . . . . .
H12A H 0.271383 0.407828 0.662572 0.033 Uiso 1 1 calc R U . . .
H12B H 0.195878 0.490016 0.699407 0.033 Uiso 1 1 calc R U . . .
C13 C 0.10597(9) 0.34280(9) 0.67324(4) 0.0261(2) Uani 1 1 d . . . . .
C14 C 0.11247(9) 0.24160(10) 0.70941(4) 0.0286(2) Uani 1 1 d . . . . .
C15 C 0.19196(11) 0.24273(11) 0.75037(5) 0.0359(3) Uani 1 1 d . . . . .
H15 H 0.241719 0.307119 0.754398 0.043 Uiso 1 1 calc R U . . .
C16 C 0.19708(12) 0.14807(12) 0.78514(5) 0.0419(3) Uani 1 1 d . . . . .
H16 H 0.249519 0.149836 0.812654 0.050 Uiso 1 1 calc R U . . .
C17 C 0.12460(12) 0.05129(12) 0.77904(5) 0.0426(3) Uani 1 1 d . . . . .
H17 H 0.128067 -0.011868 0.802450 0.051 Uiso 1 1 calc R U . . .
C18 C 0.04664(12) 0.04858(12) 0.73790(5) 0.0425(3) Uani 1 1 d . . . . .
H18 H -0.001456 -0.017030 0.733549 0.051 Uiso 1 1 calc R U . . .
C19 C 0.04001(11) 0.14290(11) 0.70331(5) 0.0351(3) Uani 1 1 d . . . . .
H19 H -0.012763 0.140658 0.675942 0.042 Uiso 1 1 calc R U . . .
C20 C 0.51395(11) 0.76808(10) 0.51166(4) 0.0337(3) Uani 1 1 d . . . . .
H20A H 0.446401 0.804108 0.496647 0.051 Uiso 1 1 calc R U . . .
H20B H 0.568533 0.750117 0.484549 0.051 Uiso 1 1 calc R U . . .
H20C H 0.548425 0.822108 0.536165 0.051 Uiso 1 1 calc R U . . .
C21 C 0.14134(11) 0.64086(10) 0.62857(5) 0.0335(3) Uani 1 1 d . . . . .
H21A H 0.102655 0.675809 0.599171 0.050 Uiso 1 1 calc R U . . .
H21B H 0.217617 0.673914 0.631604 0.050 Uiso 1 1 calc R U . . .
H21C H 0.098330 0.657395 0.659781 0.050 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 N2 1.4083(12) . ?
O1 C11 1.4715(12) . ?
N1 C1 1.3705(14) . ?
N1 C9 1.3210(14) . ?
C1 C2 1.4172(15) . ?
C1 C6 1.4210(15) . ?
N2 C13 1.2816(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.3676(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.4065(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.3677(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.4166(15) . ?
C6 C7 1.4261(15) . ?
C7 C8 1.3695(15) . ?
C7 C20 1.5017(15) . ?
C8 H8 0.9300 . ?
C8 C9 1.4168(15) . ?
C9 C10 1.5049(15) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.5383(14) . ?
C11 C12 1.5291(14) . ?
C11 C21 1.5136(15) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.5016(14) . ?
C13 C14 1.4689(15) . ?
C14 C15 1.3951(17) . ?
C14 C19 1.3984(16) . ?
C15 H15 0.9300 . ?
C15 C16 1.3886(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.3836(18) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
N2 O1 C11 109.51(7) . . ?
C9 N1 C1 117.60(9) . . ?
N1 C1 C2 117.70(10) . . ?
N1 C1 C6 123.08(10) . . ?
C2 C1 C6 119.21(10) . . ?
C13 N2 O1 109.30(9) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.56(11) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.42(11) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.29(11) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.99(11) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 118.00(10) . . ?
C5 C6 C1 118.52(10) . . ?
C5 C6 C7 123.47(10) . . ?
C6 C7 C20 120.87(10) . . ?
C8 C7 C6 117.40(10) . . ?
C8 C7 C20 121.71(10) . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.11(10) . . ?
C9 C8 H8 119.4 . . ?
N1 C9 C8 122.80(10) . . ?
N1 C9 C10 116.77(10) . . ?
C8 C9 C10 120.43(10) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C9 C10 C11 114.88(9) . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
O1 C11 C10 104.95(8) . . ?
O1 C11 C12 103.49(8) . . ?
O1 C11 C21 107.09(9) . . ?
C12 C11 C10 112.68(9) . . ?
C21 C11 C10 113.28(9) . . ?
C21 C11 C12 114.22(9) . . ?
C11 C12 H12A 111.5 . . ?
C11 C12 H12B 111.5 . . ?
H12A C12 H12B 109.4 . . ?
C13 C12 C11 101.16(8) . . ?
C13 C12 H12A 111.5 . . ?
C13 C12 H12B 111.5 . . ?
N2 C13 C12 113.93(9) . . ?
N2 C13 C14 120.73(10) . . ?
C14 C13 C12 125.27(10) . . ?
C15 C14 C13 120.10(10) . . ?
C15 C14 C19 119.07(11) . . ?
C19 C14 C13 120.84(10) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.26(12) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.28(13) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.82(12) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.39(12) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.17(12) . . ?
C18 C19 H19 119.9 . . ?
C7 C20 H20A 109.5 . . ?
C7 C20 H20B 109.5 . . ?
C7 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C11 C21 H21A 109.5 . . ?
C11 C21 H21B 109.5 . . ?
C11 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 N2 C13 C12 0.46(12) . . . . ?
O1 N2 C13 C14 177.78(9) . . . . ?
O1 C11 C12 C13 14.74(10) . . . . ?
N1 C1 C2 C3 178.99(10) . . . . ?
N1 C1 C6 C5 -179.64(9) . . . . ?
N1 C1 C6 C7 -0.68(15) . . . . ?
N1 C9 C10 C11 86.33(12) . . . . ?
C1 N1 C9 C8 0.28(15) . . . . ?
C1 N1 C9 C10 179.74(9) . . . . ?
C1 C2 C3 C4 0.55(18) . . . . ?
C1 C6 C7 C8 0.80(14) . . . . ?
C1 C6 C7 C20 -177.61(9) . . . . ?
N2 O1 C11 C10 102.48(9) . . . . ?
N2 O1 C11 C12 -15.85(10) . . . . ?
N2 O1 C11 C21 -136.85(9) . . . . ?
N2 C13 C14 C15 -163.25(11) . . . . ?
N2 C13 C14 C19 17.05(16) . . . . ?
C2 C1 C6 C5 -0.55(15) . . . . ?
C2 C1 C6 C7 178.41(9) . . . . ?
C2 C3 C4 C5 -0.24(18) . . . . ?
C3 C4 C5 C6 -0.48(17) . . . . ?
C4 C5 C6 C1 0.87(16) . . . . ?
C4 C5 C6 C7 -178.03(10) . . . . ?
C5 C6 C7 C8 179.70(10) . . . . ?
C5 C6 C7 C20 1.29(15) . . . . ?
C6 C1 C2 C3 -0.15(17) . . . . ?
C6 C7 C8 C9 -0.44(15) . . . . ?
C7 C8 C9 N1 -0.12(16) . . . . ?
C7 C8 C9 C10 -179.56(9) . . . . ?
C8 C9 C10 C11 -94.20(12) . . . . ?
C9 N1 C1 C2 -178.97(10) . . . . ?
C9 N1 C1 C6 0.13(15) . . . . ?
C9 C10 C11 O1 179.17(8) . . . . ?
C9 C10 C11 C12 -68.91(12) . . . . ?
C9 C10 C11 C21 62.69(12) . . . . ?
C10 C11 C12 C13 -98.08(10) . . . . ?
C11 O1 N2 C13 10.17(11) . . . . ?
C11 C12 C13 N2 -10.10(12) . . . . ?
C11 C12 C13 C14 172.73(9) . . . . ?
C12 C13 C14 C15 13.74(16) . . . . ?
C12 C13 C14 C19 -165.95(11) . . . . ?
C13 C14 C15 C16 178.97(11) . . . . ?
C13 C14 C19 C18 -179.59(11) . . . . ?
C14 C15 C16 C17 0.90(19) . . . . ?
C15 C14 C19 C18 0.71(17) . . . . ?
C15 C16 C17 C18 0.2(2) . . . . ?
C16 C17 C18 C19 -0.81(19) . . . . ?
C17 C18 C19 C14 0.36(19) . . . . ?
C19 C14 C15 C16 -1.34(18) . . . . ?
C20 C7 C8 C9 177.96(9) . . . . ?
C21 C11 C12 C13 130.79(10) . . . . ?

_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 1.459
_oxdiff_exptl_absorpt_empirical_full_min 0.552
####################################################################### 
# 
# 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_ytt-203
_audit_block_doi                 10.5517/ccdc.csd.cc2d57xr
_database_code_depnum_ccdc_archive 'CCDC 2209584'
loop_
_audit_author_name
_audit_author_address
heyutao
;Jinan University
China
;
_audit_update_record             
;
2022-09-26 deposited with the CCDC.	2023-08-06 downloaded from the CCDC.
;
_audit_creation_date             2022-07-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 Cl N2 O'
_chemical_formula_sum            'C20 H17 Cl N2 O'
_chemical_formula_weight         336.80
_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'
Cl Cl 0.3639 0.7018 '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                   14.3458(4)
_cell_length_b                   11.8545(3)
_cell_length_c                   10.1259(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.391(3)
_cell_angle_gamma                90
_cell_volume                     1652.05(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4066
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.6060
_cell_measurement_theta_min      3.7160
_shelx_estimated_absorpt_T_max   0.771
_shelx_estimated_absorpt_T_min   0.743
_exptl_absorpt_coefficient_mu    2.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23797
_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    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6096
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.657
_diffrn_reflns_theta_min         3.211
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00  72.00   1.00    1.00    --   40.73 -99.00 -60.00   55
  2  ω     53.00 138.00   1.00    1.00    --  107.58 -77.00-150.00   85
  3  ω     70.00  97.00   1.00    1.00    --   40.73  38.00 -90.00   27
  4  ω     78.00 177.00   1.00    1.00    --  107.58  61.00   0.00   99
  5  ω     99.00 131.00   1.00    1.00    --  107.58 125.00-120.00   32
  6  ω     89.00 142.00   1.00    1.00    --  107.58  77.00-120.00   53
  7  ω     35.00  97.00   1.00    1.00    --  107.58-111.00 114.00   62
  8  ω     24.00  86.00   1.00    1.00    --   40.73-125.00  90.00   62
  9  ω     28.00 107.00   1.00    1.00    --  107.58 -95.00 150.00   79
 10  ω   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00 -90.00   99
;
_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      0.0254169000
_diffrn_orient_matrix_UB_12      -0.1207822000
_diffrn_orient_matrix_UB_13      -0.0338028000
_diffrn_orient_matrix_UB_21      0.1027635000
_diffrn_orient_matrix_UB_22      0.0397192000
_diffrn_orient_matrix_UB_23      0.0015723000
_diffrn_orient_matrix_UB_31      0.0367969000
_diffrn_orient_matrix_UB_32      -0.0270018000
_diffrn_orient_matrix_UB_33      0.1546710000
_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                2877
_reflns_number_total             3241
_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 1.171.38.43f (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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.0056(7)
_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   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.047
_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)+(0.0963P)²+0.3910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1554
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C15(H15), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
Cl1 Cl 0.58625(4) 0.91081(7) 0.15965(7) 0.0652(3) Uani 1 1 d . . . . .
O1 O 0.20194(9) 0.97259(11) 0.60347(14) 0.0328(3) Uani 1 1 d . . . . .
N1 N 0.16313(10) 0.59929(12) 0.50076(14) 0.0251(3) Uani 1 1 d . . . . .
C1 C 0.16191(11) 0.48714(15) 0.53192(17) 0.0253(4) Uani 1 1 d . . . . .
N2 N 0.25782(11) 0.99551(13) 0.51105(17) 0.0317(4) Uani 1 1 d . . . . .
C2 C 0.20786(13) 0.41102(16) 0.4618(2) 0.0325(4) Uani 1 1 d . . . . .
H2 H 0.234878 0.437970 0.394528 0.039 Uiso 1 1 calc R U . . .
C3 C 0.21268(14) 0.29836(17) 0.4924(2) 0.0393(5) Uani 1 1 d . . . . .
H3 H 0.244198 0.249514 0.447258 0.047 Uiso 1 1 calc R U . . .
C4 C 0.17019(15) 0.25597(17) 0.5917(2) 0.0408(5) Uani 1 1 d . . . . .
H4 H 0.174132 0.179374 0.612390 0.049 Uiso 1 1 calc R U . . .
C5 C 0.12334(14) 0.32679(16) 0.6576(2) 0.0345(4) Uani 1 1 d . . . . .
H5 H 0.094605 0.297459 0.721780 0.041 Uiso 1 1 calc R U . . .
C6 C 0.11743(11) 0.44400(15) 0.63040(17) 0.0255(4) Uani 1 1 d . . . . .
C7 C 0.06865(11) 0.52151(15) 0.69527(16) 0.0252(4) Uani 1 1 d . . . . .
C8 C 0.07092(12) 0.63301(16) 0.66181(17) 0.0261(4) Uani 1 1 d . . . . .
H8 H 0.039928 0.685821 0.702689 0.031 Uiso 1 1 calc R U . . .
C9 C 0.11986(11) 0.66929(14) 0.56567(16) 0.0232(4) Uani 1 1 d . . . . .
C10 C 0.12437(12) 0.79307(15) 0.53553(17) 0.0263(4) Uani 1 1 d . . . . .
H10A H 0.064663 0.828822 0.540609 0.032 Uiso 1 1 calc R U . . .
H10B H 0.129011 0.802328 0.442416 0.032 Uiso 1 1 calc R U . . .
C11 C 0.21047(13) 0.85211(15) 0.63524(18) 0.0281(4) Uani 1 1 d . . . . .
H11 H 0.211281 0.838222 0.730966 0.034 Uiso 1 1 calc R U . . .
C12 C 0.30728(12) 0.82090(16) 0.61156(19) 0.0311(4) Uani 1 1 d . . . . .
H12A H 0.360070 0.824468 0.695996 0.037 Uiso 1 1 calc R U . . .
H12B H 0.305439 0.746512 0.570992 0.037 Uiso 1 1 calc R U . . .
C13 C 0.31501(12) 0.91227(15) 0.51246(19) 0.0280(4) Uani 1 1 d . . . . .
C14 C 0.38056(12) 0.91223(15) 0.42420(19) 0.0300(4) Uani 1 1 d . . . . .
C15 C 0.45595(14) 0.83380(18) 0.4471(2) 0.0383(5) Uani 1 1 d . . . . .
H15 H 0.463721 0.781127 0.517465 0.046 Uiso 1 1 calc R U . . .
C16 C 0.51958(14) 0.8335(2) 0.3659(2) 0.0453(5) Uani 1 1 d . . . . .
H16 H 0.570137 0.781584 0.382169 0.054 Uiso 1 1 calc R U . . .
C17 C 0.50679(15) 0.9110(2) 0.2614(2) 0.0420(5) Uani 1 1 d . . . . .
C18 C 0.43207(16) 0.9891(2) 0.2354(2) 0.0448(5) Uani 1 1 d . . . . .
H18 H 0.423886 1.040377 0.163487 0.054 Uiso 1 1 calc R U . . .
C19 C 0.36969(14) 0.98996(19) 0.3175(2) 0.0389(5) Uani 1 1 d . . . . .
H19 H 0.319955 1.042965 0.301473 0.047 Uiso 1 1 calc R U . . .
C20 C 0.01538(14) 0.48162(18) 0.79503(19) 0.0337(4) Uani 1 1 d . . . . .
H20A H 0.060944 0.450163 0.874868 0.051 Uiso 1 1 calc R U . . .
H20B H -0.031173 0.425087 0.751836 0.051 Uiso 1 1 calc R U . . .
H20C H -0.017618 0.544156 0.822049 0.051 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
Cl1 C17 1.739(2) . ?
O1 N2 1.4197(19) . ?
O1 C11 1.462(2) . ?
N1 C1 1.368(2) . ?
N1 C9 1.318(2) . ?
C1 C2 1.420(2) . ?
C1 C6 1.422(2) . ?
N2 C13 1.281(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.408(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.414(3) . ?
C6 C7 1.423(2) . ?
C7 C8 1.367(3) . ?
C7 C20 1.505(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.418(2) . ?
C9 C10 1.504(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.527(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.520(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.502(3) . ?
C13 C14 1.469(3) . ?
C14 C15 1.395(3) . ?
C14 C19 1.395(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(4) . ?
C17 C18 1.384(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(3) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
N2 O1 C11 107.72(12) . . ?
C9 N1 C1 117.30(15) . . ?
N1 C1 C2 117.66(16) . . ?
N1 C1 C6 123.29(16) . . ?
C2 C1 C6 119.05(17) . . ?
C13 N2 O1 108.92(15) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.52(19) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.38(18) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.19(19) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.41(19) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 117.90(16) . . ?
C5 C6 C1 118.40(17) . . ?
C5 C6 C7 123.70(16) . . ?
C6 C7 C20 121.07(16) . . ?
C8 C7 C6 117.43(15) . . ?
C8 C7 C20 121.49(16) . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 120.95(16) . . ?
C9 C8 H8 119.5 . . ?
N1 C9 C8 123.06(16) . . ?
N1 C9 C10 117.38(15) . . ?
C8 C9 C10 119.55(15) . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C9 C10 C11 112.72(14) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
O1 C11 C10 107.49(14) . . ?
O1 C11 H11 111.0 . . ?
O1 C11 C12 103.09(13) . . ?
C10 C11 H11 111.0 . . ?
C12 C11 C10 112.87(15) . . ?
C12 C11 H11 111.0 . . ?
C11 C12 H12A 111.8 . . ?
C11 C12 H12B 111.8 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 C11 99.95(14) . . ?
C13 C12 H12A 111.8 . . ?
C13 C12 H12B 111.8 . . ?
N2 C13 C12 113.29(17) . . ?
N2 C13 C14 120.77(17) . . ?
C14 C13 C12 125.94(16) . . ?
C15 C14 C13 119.89(17) . . ?
C19 C14 C13 121.35(17) . . ?
C19 C14 C15 118.76(19) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.1(2) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 Cl1 119.21(18) . . ?
C16 C17 C18 121.4(2) . . ?
C18 C17 Cl1 119.38(18) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.2(2) . . ?
C19 C18 H18 120.4 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C7 C20 H20A 109.5 . . ?
C7 C20 H20B 109.5 . . ?
C7 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
Cl1 C17 C18 C19 -179.22(16) . . . . ?
O1 N2 C13 C12 -1.7(2) . . . . ?
O1 N2 C13 C14 178.94(14) . . . . ?
O1 C11 C12 C13 -24.40(16) . . . . ?
N1 C1 C2 C3 177.29(16) . . . . ?
N1 C1 C6 C5 -177.99(15) . . . . ?
N1 C1 C6 C7 2.5(2) . . . . ?
N1 C9 C10 C11 -92.37(18) . . . . ?
C1 N1 C9 C8 -1.7(2) . . . . ?
C1 N1 C9 C10 177.74(14) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C6 C7 C8 -2.3(2) . . . . ?
C1 C6 C7 C20 176.78(14) . . . . ?
N2 O1 C11 C10 -93.93(15) . . . . ?
N2 O1 C11 C12 25.53(17) . . . . ?
N2 C13 C14 C15 166.52(18) . . . . ?
N2 C13 C14 C19 -13.0(3) . . . . ?
C2 C1 C6 C5 1.9(2) . . . . ?
C2 C1 C6 C7 -177.60(15) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 179.39(16) . . . . ?
C5 C6 C7 C8 178.30(15) . . . . ?
C5 C6 C7 C20 -2.7(2) . . . . ?
C6 C1 C2 C3 -2.6(3) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 N1 1.9(2) . . . . ?
C7 C8 C9 C10 -177.54(14) . . . . ?
C8 C9 C10 C11 87.10(18) . . . . ?
C9 N1 C1 C2 179.61(15) . . . . ?
C9 N1 C1 C6 -0.5(2) . . . . ?
C9 C10 C11 O1 -174.96(13) . . . . ?
C9 C10 C11 C12 72.04(19) . . . . ?
C10 C11 C12 C13 91.26(16) . . . . ?
C11 O1 N2 C13 -15.67(18) . . . . ?
C11 C12 C13 N2 17.07(19) . . . . ?
C11 C12 C13 C14 -163.57(16) . . . . ?
C12 C13 C14 C15 -12.8(3) . . . . ?
C12 C13 C14 C19 167.69(18) . . . . ?
C13 C14 C15 C16 -179.05(18) . . . . ?
C13 C14 C19 C18 179.88(18) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C14 C19 C18 0.4(3) . . . . ?
C15 C16 C17 Cl1 -179.97(16) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C14 -1.0(3) . . . . ?
C19 C14 C15 C16 0.5(3) . . . . ?
C20 C7 C8 C9 -178.81(14) . . . . ?

_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 3.533
_oxdiff_exptl_absorpt_empirical_full_min 0.546
####################################################################### 
# 
# 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_228-2_2
_audit_block_doi                 10.5517/ccdc.csd.cc2d57zt
_database_code_depnum_ccdc_archive 'CCDC 2209586'
loop_
_audit_author_name
_audit_author_address
heyutao
;Jinan University
China
;
_audit_update_record             
;
2022-09-26 deposited with the CCDC.	2023-08-06 downloaded from the CCDC.
;
_audit_creation_date             2022-07-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 N2 O'
_chemical_formula_sum            'C21 H20 N2 O'
_chemical_formula_weight         316.39
_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                   8.4599(5)
_cell_length_b                   9.7370(6)
_cell_length_c                   11.2374(6)
_cell_angle_alpha                66.551(5)
_cell_angle_beta                 78.251(5)
_cell_angle_gamma                79.553(5)
_cell_volume                     826.23(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3708
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.2970
_cell_measurement_theta_min      4.3230
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75010
_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    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.15
_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  0.0213
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5380
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.586
_diffrn_reflns_theta_min         4.335
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_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    -88.00 -17.00   1.00    1.00    --  -40.73 -38.00   0.00   71
  2  ω     43.00  97.00   1.00    1.00    --   40.73-125.00-180.00   54
  3  ω     64.00 129.00   1.00    1.00    --  107.58 -45.00-150.00   65
  4  ω     84.00 110.00   1.00    1.00    --  107.58 -95.00 -30.00   26
  5  ω     42.00 100.00   1.00    1.00    --  107.58 -95.00  60.00   58
  6  ω     40.00  69.00   1.00    1.00    --  107.58 -61.00 -30.00   29
  7  ω     42.00 110.00   1.00    1.00    --  107.58 -95.00 -90.00   68
  8  ω     38.00 116.00   1.00    1.00    --  107.58-125.00-150.00   78
  9  ω     85.00 178.00   1.00    1.00    --  107.58  61.00  30.00   93
 10  ω    110.00 164.00   1.00    1.00    --  107.58 125.00-120.00   54
 11  ω     99.00 127.00   1.00    1.00    --  107.58 125.00-150.00   28
 12  ω     95.00 168.00   1.00    1.00    --  107.58 125.00 -30.00   73
 13  ω     82.00 164.00   1.00    1.00    --  107.58  45.00 150.00   82
 14  ω     78.00 157.00   1.00    1.00    --  107.58  61.00  90.00   79
 15  ω     68.00 117.00   1.00    1.00    --   40.73 167.00  64.00   49
 16  ω    -56.00  -3.00   1.00    1.00    --  -40.73 125.00-180.00   53
 17  ω   -118.00  -7.00   1.00    1.00    --  -40.73 -19.00  90.00  111
;
_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      -0.0554884000
_diffrn_orient_matrix_UB_12      0.1627838000
_diffrn_orient_matrix_UB_13      -0.0871060000
_diffrn_orient_matrix_UB_21      0.1030172000
_diffrn_orient_matrix_UB_22      -0.0250768000
_diffrn_orient_matrix_UB_23      -0.1210302000
_diffrn_orient_matrix_UB_31      -0.1460855000
_diffrn_orient_matrix_UB_32      -0.0546855000
_diffrn_orient_matrix_UB_33      -0.0240619000
_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                2929
_reflns_number_total             3214
_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 1.171.38.43f (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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0154(16)
_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   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         3214
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.001
_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)+(0.0616P)²+0.1610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1153
_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. Rigid body (RIGU) restrains
 N1A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N1, C7, C5, C1, C6, C2, C9, C3, C4, C8
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Others
 Sof(C11A)=Sof(H11A)=1-FVAR(1)
 Sof(C11)=Sof(H11)=FVAR(1)
 Sof(C10A)=Sof(H10A)=Sof(H10B)=1-FVAR(2)
 Sof(C10)=Sof(H10C)=Sof(H10D)=FVAR(2)
 Sof(N1A)=Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=1-
 FVAR(3)
 Sof(N1)=Sof(C7)=Sof(C5)=Sof(H5)=Sof(C1)=Sof(C6)=Sof(C2)=Sof(H2)=Sof(C9)=
 Sof(H9)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C8)=Sof(H8)=FVAR(3)
4.a Ternary CH refined with riding coordinates:
 C11A(H11A), C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C10A(H10A,H10B), C10(H10C,H10D)
4.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C2A(H2A), C3A(H3A),
 C4A(H4A), C5A(H5A), C8A(H8A), C9A(H9A), C5(H5), C2(H2), C9(H9), C3(H3), C4(H4),
  C8(H8)
4.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), 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 0.20118(12) 0.49084(10) 0.39641(9) 0.0443(3) Uani 1 1 d . . . . .
N2 N 0.29106(13) 0.42651(11) 0.50313(10) 0.0389(3) Uani 1 1 d . . . . .
C12 C 0.20012(16) 0.22709(13) 0.47727(12) 0.0378(3) Uani 1 1 d . . . . .
C13 C 0.29723(15) 0.28285(13) 0.54606(11) 0.0336(3) Uani 1 1 d . . . . .
C14 C 0.39560(15) 0.19048(13) 0.65088(12) 0.0335(3) Uani 1 1 d . . . . .
C15 C 0.53997(16) 0.23921(15) 0.65404(13) 0.0411(3) Uani 1 1 d . . . . .
H15 H 0.572244 0.329507 0.590576 0.049 Uiso 1 1 calc R U . . .
C16 C 0.63493(16) 0.15417(17) 0.75078(14) 0.0460(3) Uani 1 1 d . . . . .
H16 H 0.729690 0.188355 0.752910 0.055 Uiso 1 1 calc R U . . .
C17 C 0.58970(17) 0.01867(17) 0.84427(14) 0.0457(3) Uani 1 1 d . . . . .
H17 H 0.654862 -0.039268 0.908245 0.055 Uiso 1 1 calc R U . . .
C18 C 0.44691(17) -0.03063(15) 0.84240(13) 0.0425(3) Uani 1 1 d . . . . .
H18 H 0.415796 -0.121307 0.905970 0.051 Uiso 1 1 calc R U . . .
C19 C 0.35007(15) 0.05420(14) 0.74649(12) 0.0364(3) Uani 1 1 d . . . . .
H19 H 0.254488 0.020179 0.745876 0.044 Uiso 1 1 calc R U . . .
C20 C 0.28705(19) 0.09282(15) 0.44410(14) 0.0478(4) Uani 1 1 d . . . . .
H20A H 0.393400 0.115034 0.397048 0.072 Uiso 1 1 calc R U . . .
H20B H 0.225975 0.072637 0.390763 0.072 Uiso 1 1 calc R U . . .
H20C H 0.296619 0.006100 0.523573 0.072 Uiso 1 1 calc R U . . .
C21 C 0.03292(17) 0.19308(16) 0.55791(15) 0.0462(3) Uani 1 1 d . . . . .
H21A H 0.045628 0.109983 0.639254 0.069 Uiso 1 1 calc R U . . .
H21B H -0.030968 0.167702 0.509655 0.069 Uiso 1 1 calc R U . . .
H21C H -0.020824 0.280196 0.575424 0.069 Uiso 1 1 calc R U . . .
N1A N 0.0364(16) 0.7985(18) -0.0831(14) 0.055(3) Uani 0.237(5) 1 d . . P A 2
C1A C 0.1509(19) 0.6894(16) -0.1060(11) 0.042(2) Uani 0.237(5) 1 d . . P A 2
C2A C 0.2131(15) 0.7065(12) -0.2390(8) 0.064(2) Uani 0.237(5) 1 d . . P A 2
H2A H 0.172941 0.790072 -0.306349 0.077 Uiso 0.237(5) 1 calc R U P A 2
C3A C 0.3270(13) 0.6065(12) -0.2697(10) 0.070(2) Uani 0.237(5) 1 d . . P A 2
H3A H 0.366371 0.620913 -0.356854 0.084 Uiso 0.237(5) 1 calc R U P A 2
C4A C 0.3873(18) 0.4770(14) -0.1662(13) 0.062(3) Uani 0.237(5) 1 d . . P A 2
H4A H 0.466733 0.407609 -0.187702 0.074 Uiso 0.237(5) 1 calc R U P A 2
C5A C 0.3334(9) 0.4517(10) -0.0390(9) 0.0511(18) Uani 0.237(5) 1 d . . P A 2
H5A H 0.374049 0.366250 0.026650 0.061 Uiso 0.237(5) 1 calc R U P A 2
C6A C 0.2108(13) 0.5607(12) -0.0068(9) 0.0348(18) Uani 0.237(5) 1 d . . P A 2
C7A C 0.1423(12) 0.5369(9) 0.1248(8) 0.0331(16) Uani 0.237(5) 1 d . . P A 2
C8A C 0.0315(14) 0.6423(14) 0.1472(10) 0.044(2) Uani 0.237(5) 1 d . . P A 2
H8A H -0.015634 0.628425 0.232891 0.053 Uiso 0.237(5) 1 calc R U P A 2
C9A C -0.015(2) 0.7714(17) 0.0467(13) 0.055(4) Uani 0.237(5) 1 d . . P A 2
H9A H -0.086998 0.845182 0.068449 0.066 Uiso 0.237(5) 1 calc R U P A 2
C10A C 0.1977(6) 0.3948(6) 0.2351(5) 0.0338(16) Uani 0.227(4) 1 d . . P A 2
H10A H 0.176869 0.308566 0.220203 0.041 Uiso 0.227(4) 1 calc R U P A 2
H10B H 0.314331 0.389569 0.230277 0.041 Uiso 0.227(4) 1 calc R U P A 2
C11A C 0.1199(18) 0.3810(7) 0.3710(7) 0.036(2) Uani 0.241(10) 1 d . . P A 2
H11A H 0.000920 0.396165 0.384083 0.044 Uiso 0.241(10) 1 calc R U P A 2
N1 N 0.0870(4) 0.7968(5) -0.0901(4) 0.0464(7) Uani 0.763(5) 1 d . . P A 1
C7 C 0.0767(3) 0.5408(3) 0.1498(3) 0.0342(6) Uani 0.763(5) 1 d . . P A 1
C5 C 0.2807(3) 0.4018(2) 0.0287(2) 0.0400(5) Uani 0.763(5) 1 d . . P A 1
H5 H 0.283650 0.315092 0.104265 0.048 Uiso 0.763(5) 1 calc R U P A 1
C10 C 0.06280(19) 0.40593(18) 0.27662(16) 0.0365(5) Uani 0.773(4) 1 d . . P A 1
H10C H 0.052482 0.319124 0.257983 0.044 Uiso 0.773(4) 1 calc R U P A 1
H10D H -0.035605 0.424128 0.332502 0.044 Uiso 0.773(4) 1 calc R U P A 1
C1 C 0.1814(5) 0.6639(4) -0.0825(4) 0.0402(7) Uani 0.763(5) 1 d . . P A 1
C6 C 0.1803(4) 0.5328(3) 0.0346(3) 0.0341(6) Uani 0.763(5) 1 d . . P A 1
C2 C 0.2791(3) 0.6590(3) -0.1998(2) 0.0465(5) Uani 0.763(5) 1 d . . P A 1
H2 H 0.279270 0.744802 -0.276247 0.056 Uiso 0.763(5) 1 calc R U P A 1
C9 C -0.0061(6) 0.7989(5) 0.0183(4) 0.0438(8) Uani 0.763(5) 1 d . . P A 1
H9 H -0.071499 0.887785 0.014922 0.053 Uiso 0.763(5) 1 calc R U P A 1
C3 C 0.3729(4) 0.5298(4) -0.2020(3) 0.0478(7) Uani 0.763(5) 1 d . . P A 1
H3 H 0.435868 0.527471 -0.279436 0.057 Uiso 0.763(5) 1 calc R U P A 1
C11 C 0.2057(5) 0.3693(2) 0.3504(2) 0.0321(6) Uani 0.759(10) 1 d . . P A 1
H11 H 0.307603 0.362499 0.292134 0.039 Uiso 0.759(10) 1 calc R U P A 1
C4 C 0.3735(3) 0.3999(3) -0.0858(3) 0.0460(6) Uani 0.763(5) 1 d . . P A 1
H4 H 0.437691 0.312065 -0.086934 0.055 Uiso 0.763(5) 1 calc R U P A 1
C8 C -0.0137(4) 0.6752(4) 0.1397(3) 0.0390(6) Uani 0.763(5) 1 d . . P A 1
H8 H -0.080630 0.685496 0.213042 0.047 Uiso 0.763(5) 1 calc R U P A 1


_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 N2 1.4176(13) . ?
O1 C11A 1.512(7) . ?
O1 C11 1.460(2) . ?
N2 C13 1.2802(16) . ?
C12 C13 1.5237(16) . ?
C12 C20 1.5220(17) . ?
C12 C21 1.530(2) . ?
C12 C11A 1.634(8) . ?
C12 C11 1.542(2) . ?
C13 C14 1.4743(17) . ?
C14 C15 1.3998(18) . ?
C14 C19 1.3949(17) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.3859(18) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1A C1A 1.369(14) . ?
N1A C9A 1.365(15) . ?
C1A C2A 1.433(13) . ?
C1A C6A 1.399(12) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.337(14) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.430(14) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.345(13) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.444(13) . ?
C6A C7A 1.416(9) . ?
C7A C8A 1.325(11) . ?
C7A C10A 1.519(9) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.373(14) . ?
C9A H9A 0.9300 . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C10A C11A 1.498(11) . ?
C11A H11A 0.9800 . ?
N1 C1 1.372(4) . ?
N1 C9 1.315(5) . ?
C7 C10 1.506(3) . ?
C7 C6 1.430(3) . ?
C7 C8 1.366(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.416(3) . ?
C5 C4 1.368(3) . ?
C10 H10C 0.9700 . ?
C10 H10D 0.9700 . ?
C10 C11 1.514(3) . ?
C1 C6 1.422(3) . ?
C1 C2 1.420(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.414(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.411(3) . ?
C11 H11 0.9800 . ?
C4 H4 0.9300 . ?
C8 H8 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
N2 O1 C11A 115.3(3) . . ?
N2 O1 C11 104.67(12) . . ?
C13 N2 O1 109.15(10) . . ?
C13 C12 C21 110.26(10) . . ?
C13 C12 C11A 104.3(3) . . ?
C13 C12 C11 95.23(12) . . ?
C20 C12 C13 114.06(11) . . ?
C20 C12 C21 110.96(11) . . ?
C20 C12 C11A 123.7(3) . . ?
C20 C12 C11 108.68(15) . . ?
C21 C12 C11A 91.1(5) . . ?
C21 C12 C11 116.93(19) . . ?
N2 C13 C12 113.70(11) . . ?
N2 C13 C14 119.04(11) . . ?
C14 C13 C12 127.25(10) . . ?
C15 C14 C13 119.38(11) . . ?
C19 C14 C13 121.82(11) . . ?
C19 C14 C15 118.79(12) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.51(13) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.28(13) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.76(13) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.48(13) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.17(12) . . ?
C18 C19 H19 119.9 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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 . . ?
C9A N1A C1A 114.0(14) . . ?
N1A C1A C2A 118.6(10) . . ?
N1A C1A C6A 123.9(12) . . ?
C6A C1A C2A 117.5(11) . . ?
C1A C2A H2A 118.9 . . ?
C3A C2A C1A 122.3(10) . . ?
C3A C2A H2A 118.9 . . ?
C2A C3A H3A 120.6 . . ?
C2A C3A C4A 118.9(9) . . ?
C4A C3A H3A 120.6 . . ?
C3A C4A H4A 118.8 . . ?
C5A C4A C3A 122.4(10) . . ?
C5A C4A H4A 118.8 . . ?
C4A C5A H5A 120.9 . . ?
C4A C5A C6A 118.2(9) . . ?
C6A C5A H5A 120.9 . . ?
C1A C6A C5A 120.6(9) . . ?
C1A C6A C7A 118.2(10) . . ?
C7A C6A C5A 121.1(8) . . ?
C6A C7A C10A 120.0(8) . . ?
C8A C7A C6A 117.9(8) . . ?
C8A C7A C10A 122.1(8) . . ?
C7A C8A H8A 119.3 . . ?
C7A C8A C9A 121.5(11) . . ?
C9A C8A H8A 119.3 . . ?
N1A C9A C8A 124.3(15) . . ?
N1A C9A H9A 117.9 . . ?
C8A C9A H9A 117.9 . . ?
C7A C10A H10A 108.3 . . ?
C7A C10A H10B 108.3 . . ?
H10A C10A H10B 107.4 . . ?
C11A C10A C7A 116.0(6) . . ?
C11A C10A H10A 108.3 . . ?
C11A C10A H10B 108.3 . . ?
O1 C11A C12 97.1(5) . . ?
O1 C11A H11A 115.1 . . ?
C12 C11A H11A 115.1 . . ?
C10A C11A O1 102.9(7) . . ?
C10A C11A C12 109.5(8) . . ?
C10A C11A H11A 115.1 . . ?
C9 N1 C1 116.5(4) . . ?
C6 C7 C10 121.8(2) . . ?
C8 C7 C10 120.8(3) . . ?
C8 C7 C6 117.3(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(2) . . ?
C7 C10 H10C 108.8 . . ?
C7 C10 H10D 108.8 . . ?
C7 C10 C11 113.87(17) . . ?
H10C C10 H10D 107.7 . . ?
C11 C10 H10C 108.8 . . ?
C11 C10 H10D 108.8 . . ?
N1 C1 C6 123.1(4) . . ?
N1 C1 C2 117.0(3) . . ?
C2 C1 C6 119.8(3) . . ?
C5 C6 C7 124.2(2) . . ?
C5 C6 C1 117.6(3) . . ?
C1 C6 C7 118.2(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.6 . . ?
N1 C9 H9 117.8 . . ?
N1 C9 C8 124.4(4) . . ?
C8 C9 H9 117.8 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
O1 C11 C12 103.60(13) . . ?
O1 C11 C10 107.4(2) . . ?
O1 C11 H11 110.0 . . ?
C12 C11 H11 110.0 . . ?
C10 C11 C12 115.4(2) . . ?
C10 C11 H11 110.0 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?

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 N2 C13 C12 -3.59(15) . . . . ?
O1 N2 C13 C14 175.27(9) . . . . ?
N2 O1 C11A C12 -6.8(8) . . . . ?
N2 O1 C11A C10A -118.7(4) . . . . ?
N2 O1 C11 C12 35.2(3) . . . . ?
N2 O1 C11 C10 157.80(15) . . . . ?
N2 C13 C14 C15 -34.63(17) . . . . ?
N2 C13 C14 C19 146.27(12) . . . . ?
C12 C13 C14 C15 144.07(13) . . . . ?
C12 C13 C14 C19 -35.04(18) . . . . ?
C13 C12 C11A O1 4.2(7) . . . . ?
C13 C12 C11A C10A 110.7(5) . . . . ?
C13 C12 C11 O1 -33.9(2) . . . . ?
C13 C12 C11 C10 -150.99(19) . . . . ?
C13 C14 C15 C16 -179.57(11) . . . . ?
C13 C14 C19 C18 179.06(11) . . . . ?
C14 C15 C16 C17 1.09(19) . . . . ?
C15 C14 C19 C18 -0.05(18) . . . . ?
C15 C16 C17 C18 -1.2(2) . . . . ?
C16 C17 C18 C19 0.8(2) . . . . ?
C17 C18 C19 C14 -0.11(19) . . . . ?
C19 C14 C15 C16 -0.44(18) . . . . ?
C20 C12 C13 N2 137.13(12) . . . . ?
C20 C12 C13 C14 -41.62(17) . . . . ?
C20 C12 C11A O1 -128.3(3) . . . . ?
C20 C12 C11A C10A -21.8(9) . . . . ?
C20 C12 C11 O1 -151.47(19) . . . . ?
C20 C12 C11 C10 91.4(2) . . . . ?
C21 C12 C13 N2 -97.25(13) . . . . ?
C21 C12 C13 C14 84.00(15) . . . . ?
C21 C12 C11A O1 115.4(6) . . . . ?
C21 C12 C11A C10A -138.1(6) . . . . ?
C21 C12 C11 O1 82.0(2) . . . . ?
C21 C12 C11 C10 -35.1(2) . . . . ?
N1A C1A C2A C3A 178.8(11) . . . . ?
N1A C1A C6A C5A -179.1(12) . . . . ?
N1A C1A C6A C7A 4.0(19) . . . . ?
C1A N1A C9A C8A -5(3) . . . . ?
C1A C2A C3A C4A 0.8(17) . . . . ?
C1A C6A C7A C8A -3.7(15) . . . . ?
C1A C6A C7A C10A 176.9(10) . . . . ?
C2A C1A C6A C5A 1.3(18) . . . . ?
C2A C1A C6A C7A -175.6(11) . . . . ?
C2A C3A C4A C5A 0.2(19) . . . . ?
C3A C4A C5A C6A -0.4(18) . . . . ?
C4A C5A C6A C1A -0.4(16) . . . . ?
C4A C5A C6A C7A 176.5(10) . . . . ?
C5A C6A C7A C8A 179.4(10) . . . . ?
C5A C6A C7A C10A 0.0(14) . . . . ?
C6A C1A C2A C3A -1.5(19) . . . . ?
C6A C7A C8A C9A -0.5(18) . . . . ?
C6A C7A C10A C11A 179.1(8) . . . . ?
C7A C8A C9A N1A 5(3) . . . . ?
C7A C10A C11A O1 -74.4(9) . . . . ?
C7A C10A C11A C12 -176.9(6) . . . . ?
C8A C7A C10A C11A -0.2(12) . . . . ?
C9A N1A C1A C2A 179.8(15) . . . . ?
C9A N1A C1A C6A 0(2) . . . . ?
C10A C7A C8A C9A 178.8(13) . . . . ?
C11A O1 N2 C13 7.1(6) . . . . ?
C11A C12 C13 N2 -0.7(5) . . . . ?
C11A C12 C13 C14 -179.5(5) . . . . ?
N1 C1 C6 C7 -0.5(5) . . . . ?
N1 C1 C6 C5 178.6(4) . . . . ?
N1 C1 C2 C3 -178.0(3) . . . . ?
N1 C9 C8 C7 -1.5(6) . . . . ?
C7 C10 C11 O1 68.1(3) . . . . ?
C7 C10 C11 C12 -177.0(2) . . . . ?
C10 C7 C6 C5 -1.5(4) . . . . ?
C10 C7 C6 C1 177.5(3) . . . . ?
C10 C7 C8 C9 -176.6(3) . . . . ?
C1 N1 C9 C8 0.4(7) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C6 C7 C10 C11 76.6(3) . . . . ?
C6 C7 C8 C9 1.5(4) . . . . ?
C6 C5 C4 C3 0.5(3) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
C2 C1 C6 C7 -178.2(3) . . . . ?
C2 C1 C6 C5 1.0(5) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C9 N1 C1 C6 0.5(6) . . . . ?
C9 N1 C1 C2 178.3(4) . . . . ?
C11 O1 N2 C13 -20.4(2) . . . . ?
C11 C12 C13 N2 24.0(2) . . . . ?
C11 C12 C13 C14 -154.77(18) . . . . ?
C4 C5 C6 C7 177.9(2) . . . . ?
C4 C5 C6 C1 -1.1(4) . . . . ?
C8 C7 C10 C11 -105.3(3) . . . . ?
C8 C7 C6 C5 -179.6(3) . . . . ?
C8 C7 C6 C1 -0.6(4) . . . . ?

_olex2_date_sample_data_collection 2022-07-21
_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 1.611
_oxdiff_exptl_absorpt_empirical_full_min 0.445
