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

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

data_l2y-a
_database_code_depnum_ccdc_archive 'CCDC 2131808'
loop_
_audit_author_name
_audit_author_address
CZY
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2021-12-30 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-12-30
_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         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_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                   7.9813(6)
_cell_length_b                   11.4019(10)
_cell_length_c                   17.8408(8)
_cell_angle_alpha                92.730(5)
_cell_angle_beta                 90.852(5)
_cell_angle_gamma                108.525(7)
_cell_volume                     1536.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5706
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2870
_cell_measurement_theta_min      2.4300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_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  0.0402
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.073
_diffrn_reflns_theta_min         2.481
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  18.00   1.00    1.00    --  -40.98  38.00  90.00   70
  2  ω    -85.00  41.00   1.00    1.00    --  -40.98   0.00  30.00  126
  3  ω     29.00  95.00   1.00    1.00    --   40.98-125.00   0.00   66
  4  ω     36.00 118.00   1.00    1.00    --  106.95 -61.00   0.00   82
  5  ω     75.00 121.00   1.00    1.00    --  106.95-125.00 -60.00   46
  6  ω     75.00 108.00   1.00    1.00    --  106.95 -94.00 -30.00   33
  7  ω     42.00 134.00   1.00    1.00    --  106.95 -61.00-120.00   92
  8  ω     88.00 152.00   1.00    1.00    --  106.95  30.00 -30.00   64
  9  ω     84.00 166.00   1.00    1.00    --  106.95  45.00 -90.00   82
 10  ω    106.00 131.00   1.00    1.00    --  106.95 125.00  90.00   25
 11  ω     31.00 137.00   1.00    1.00    --  106.95 -15.00 -60.00  106
 12  ω     84.00 118.00   1.00    1.00    --  106.95-125.00 120.00   34
 13  ω     52.00  78.00   1.00    1.00    --  106.95-125.00 120.00   26
 14  ω     41.00  67.00   1.00    1.00    --  106.95-125.00 150.00   26
 15  ω     35.00 140.00   1.00    1.00    --  106.95 -77.00 120.00  105
 16  ω     32.00 135.00   1.00    1.00    --  106.95 -30.00  90.00  103
 17  ω     28.00  82.00   1.00    1.00    --   40.98-125.00-180.00   54
 18  ω    -51.00  -7.00   1.00    1.00    --  -40.98 125.00-180.00   44
;
_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      0.1010898000
_diffrn_orient_matrix_UB_12      0.1333700000
_diffrn_orient_matrix_UB_13      0.0295930000
_diffrn_orient_matrix_UB_21      -0.1749867000
_diffrn_orient_matrix_UB_22      0.0171563000
_diffrn_orient_matrix_UB_23      0.0251087000
_diffrn_orient_matrix_UB_31      0.0253613000
_diffrn_orient_matrix_UB_32      -0.0478138000
_diffrn_orient_matrix_UB_33      0.0772960000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                5141
_reflns_number_total             6026
_reflns_odcompleteness_completeness 99.93
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6026
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.1046
_refine_ls_restrained_S_all      1.039
_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)+(0.1907P)²+3.1711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3058
_refine_ls_wR_factor_ref         0.3130
_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:
 C16(H16A,H16B), C16B(H16C,H16D)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C6B(H6B), C7B(H7B), C8B(H8B), C10B(H10B), C11B(H11B), C12B(H12B), C13B(H13B),
 C14B(H14B)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C17B(H17D,H17E,
 H17F), C18B(H18D,H18E,H18F), C19B(H19D,H19E,H19F)
;
_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 0.8892(4) 1.0060(2) 0.82260(15) 0.0363(6) Uani 1 1 d . . . . .
O2 O 1.0169(3) 0.9148(2) 0.90441(15) 0.0335(6) Uani 1 1 d . . . . .
N1 N 0.3008(4) 0.4812(3) 0.85589(17) 0.0303(7) Uani 1 1 d . . . . .
C1 C 0.7316(5) 0.7991(3) 0.85599(19) 0.0287(7) Uani 1 1 d . . . . .
C2 C 0.5620(5) 0.7990(3) 0.83690(18) 0.0280(7) Uani 1 1 d . . . . .
C3 C 0.4245(5) 0.6855(3) 0.83934(19) 0.0284(7) Uani 1 1 d . . . . .
C4 C 0.4608(5) 0.5751(3) 0.85703(18) 0.0267(7) Uani 1 1 d . . . . .
C5 C 0.6340(5) 0.5749(3) 0.87245(18) 0.0263(7) Uani 1 1 d . . . . .
C6 C 0.7647(5) 0.6895(3) 0.8755(2) 0.0287(7) Uani 1 1 d . . . . .
H6 H 0.878690 0.694439 0.890932 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2371(5) 0.6535(3) 0.8291(2) 0.0319(8) Uani 1 1 d . . . . .
H7 H 0.174007 0.706408 0.817082 0.038 Uiso 1 1 calc R U . . .
C8 C 0.1692(5) 0.5301(4) 0.8403(2) 0.0324(8) Uani 1 1 d . . . . .
H8 H 0.049356 0.485098 0.837657 0.039 Uiso 1 1 calc R U . . .
C9 C 0.6826(5) 0.4609(3) 0.88317(19) 0.0263(7) Uani 1 1 d . . . . .
C10 C 0.7506(5) 0.4390(3) 0.9516(2) 0.0325(8) Uani 1 1 d . . . . .
H10 H 0.764159 0.495942 0.992143 0.039 Uiso 1 1 calc R U . . .
C11 C 0.7984(5) 0.3336(3) 0.9602(2) 0.0352(8) Uani 1 1 d . . . . .
H11 H 0.841559 0.319499 1.006434 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7818(5) 0.2488(3) 0.8995(2) 0.0327(8) Uani 1 1 d . . . . .
H12 H 0.815026 0.178445 0.904919 0.039 Uiso 1 1 calc R U . . .
C13 C 0.7153(5) 0.2699(3) 0.8307(2) 0.0321(8) Uani 1 1 d . . . . .
H13 H 0.703640 0.213413 0.790028 0.039 Uiso 1 1 calc R U . . .
C14 C 0.6664(5) 0.3749(3) 0.82270(19) 0.0290(7) Uani 1 1 d . . . . .
H14 H 0.622185 0.388462 0.776528 0.035 Uiso 1 1 calc R U . . .
C15 C 0.8825(5) 0.9165(3) 0.8576(2) 0.0295(7) Uani 1 1 d . . . . .
C16 C 1.1641(5) 1.0288(3) 0.9113(2) 0.0348(8) Uani 1 1 d . . . . .
H16A H 1.123554 1.097088 0.928064 0.042 Uiso 1 1 calc R U . . .
H16B H 1.218379 1.047076 0.863122 0.042 Uiso 1 1 calc R U . . .
C17 C 1.2958(5) 1.0119(4) 0.9677(2) 0.0370(9) Uani 1 1 d . . . . .
H17A H 1.331114 0.941875 0.951702 0.056 Uiso 1 1 calc R U . . .
H17B H 1.242633 0.998036 1.015788 0.056 Uiso 1 1 calc R U . . .
H17C H 1.397620 1.084935 0.971612 0.056 Uiso 1 1 calc R U . . .
C18 C 0.5165(5) 0.9110(3) 0.8137(2) 0.0339(8) Uani 1 1 d . . . . .
H18A H 0.556096 0.929984 0.763853 0.051 Uiso 1 1 calc R U . . .
H18B H 0.573660 0.980305 0.847893 0.051 Uiso 1 1 calc R U . . .
H18C H 0.390783 0.893898 0.814651 0.051 Uiso 1 1 calc R U . . .
C19 C 0.2689(5) 0.3517(3) 0.8716(2) 0.0354(8) Uani 1 1 d . . . . .
H19A H 0.302532 0.309593 0.829416 0.053 Uiso 1 1 calc R U . . .
H19B H 0.145668 0.313190 0.880344 0.053 Uiso 1 1 calc R U . . .
H19C H 0.337599 0.347026 0.915305 0.053 Uiso 1 1 calc R U . . .
O1B O 0.4753(4) 0.0116(2) 0.64768(15) 0.0370(6) Uani 1 1 d . . . . .
O2B O 0.7267(3) 0.1321(2) 0.60099(16) 0.0364(6) Uani 1 1 d . . . . .
N1B N 0.3501(4) 0.5369(3) 0.64081(17) 0.0304(7) Uani 1 1 d . . . . .
C1B C 0.5153(5) 0.2279(3) 0.63596(19) 0.0284(7) Uani 1 1 d . . . . .
C2B C 0.3478(5) 0.2239(3) 0.66012(19) 0.0292(7) Uani 1 1 d . . . . .
C3B C 0.3054(5) 0.3346(3) 0.65842(18) 0.0291(7) Uani 1 1 d . . . . .
C4B C 0.4317(5) 0.4468(3) 0.63807(18) 0.0280(7) Uani 1 1 d . . . . .
C5B C 0.6054(5) 0.4527(3) 0.62043(18) 0.0274(7) Uani 1 1 d . . . . .
C6B C 0.6393(5) 0.3405(3) 0.61649(18) 0.0276(7) Uani 1 1 d . . . . .
H6B H 0.749028 0.339476 0.600254 0.033 Uiso 1 1 calc R U . . .
C7B C 0.1452(5) 0.3619(4) 0.6717(2) 0.0333(8) Uani 1 1 d . . . . .
H7B H 0.038615 0.306514 0.685703 0.040 Uiso 1 1 calc R U . . .
C8B C 0.1779(5) 0.4842(4) 0.6599(2) 0.0338(8) Uani 1 1 d . . . . .
H8B H 0.095191 0.525874 0.664283 0.041 Uiso 1 1 calc R U . . .
C9B C 0.7521(5) 0.5688(3) 0.61060(19) 0.0278(7) Uani 1 1 d . . . . .
C10B C 0.8114(5) 0.6560(3) 0.6706(2) 0.0308(8) Uani 1 1 d . . . . .
H10B H 0.752530 0.643548 0.715585 0.037 Uiso 1 1 calc R U . . .
C11B C 0.9567(5) 0.7613(3) 0.6644(2) 0.0338(8) Uani 1 1 d . . . . .
H11B H 0.995098 0.818303 0.705026 0.041 Uiso 1 1 calc R U . . .
C12B C 1.0446(5) 0.7809(3) 0.5972(2) 0.0344(8) Uani 1 1 d . . . . .
H12B H 1.142436 0.850955 0.592755 0.041 Uiso 1 1 calc R U . . .
C13B C 0.9857(5) 0.6955(3) 0.5365(2) 0.0337(8) Uani 1 1 d . . . . .
H13B H 1.043200 0.709076 0.491245 0.040 Uiso 1 1 calc R U . . .
C14B C 0.8418(5) 0.5904(3) 0.5434(2) 0.0309(8) Uani 1 1 d . . . . .
H14B H 0.804178 0.533297 0.502672 0.037 Uiso 1 1 calc R U . . .
C15B C 0.5654(5) 0.1127(3) 0.62932(19) 0.0298(7) Uani 1 1 d . . . . .
C16B C 0.7879(5) 0.0250(4) 0.5943(2) 0.0377(9) Uani 1 1 d . . . . .
H16C H 0.763724 -0.018934 0.640182 0.045 Uiso 1 1 calc R U . . .
H16D H 0.914872 0.052928 0.588391 0.045 Uiso 1 1 calc R U . . .
C17B C 0.7011(6) -0.0628(3) 0.5288(2) 0.0362(8) Uani 1 1 d . . . . .
H17D H 0.719091 -0.018860 0.483523 0.054 Uiso 1 1 calc R U . . .
H17E H 0.576675 -0.097123 0.536729 0.054 Uiso 1 1 calc R U . . .
H17F H 0.752218 -0.128449 0.524526 0.054 Uiso 1 1 calc R U . . .
C18B C 0.2160(5) 0.1120(3) 0.6902(2) 0.0336(8) Uani 1 1 d . . . . .
H18D H 0.176573 0.048172 0.650807 0.050 Uiso 1 1 calc R U . . .
H18E H 0.116729 0.133777 0.708562 0.050 Uiso 1 1 calc R U . . .
H18F H 0.270342 0.082575 0.730369 0.050 Uiso 1 1 calc R U . . .
C19B C 0.4231(6) 0.6648(4) 0.6206(2) 0.0388(9) Uani 1 1 d . . . . .
H19D H 0.501971 0.712094 0.660229 0.058 Uiso 1 1 calc R U . . .
H19E H 0.328829 0.698773 0.613168 0.058 Uiso 1 1 calc R U . . .
H19F H 0.486709 0.667882 0.575110 0.058 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 C15 1.209(4) . ?
O2 C15 1.355(5) . ?
O2 C16 1.447(4) . ?
N1 C4 1.381(5) . ?
N1 C8 1.367(5) . ?
N1 C19 1.458(5) . ?
C1 C2 1.391(5) . ?
C1 C6 1.414(5) . ?
C1 C15 1.488(5) . ?
C2 C3 1.409(5) . ?
C2 C18 1.508(5) . ?
C3 C4 1.426(5) . ?
C3 C7 1.429(5) . ?
C4 C5 1.406(5) . ?
C5 C6 1.387(5) . ?
C5 C9 1.489(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.364(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(5) . ?
C9 C14 1.399(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.392(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(5) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.507(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O1B C15B 1.212(5) . ?
O2B C15B 1.346(5) . ?
O2B C16B 1.453(4) . ?
N1B C4B 1.379(5) . ?
N1B C8B 1.370(5) . ?
N1B C19B 1.453(5) . ?
C1B C2B 1.398(5) . ?
C1B C6B 1.412(5) . ?
C1B C15B 1.490(5) . ?
C2B C3B 1.407(5) . ?
C2B C18B 1.501(5) . ?
C3B C4B 1.422(5) . ?
C3B C7B 1.430(5) . ?
C4B C5B 1.408(5) . ?
C5B C6B 1.388(5) . ?
C5B C9B 1.483(5) . ?
C6B H6B 0.9300 . ?
C7B H7B 0.9300 . ?
C7B C8B 1.362(6) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.394(5) . ?
C9B C14B 1.398(5) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.389(5) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.389(5) . ?
C12B H12B 0.9300 . ?
C12B C13B 1.391(5) . ?
C13B H13B 0.9300 . ?
C13B C14B 1.384(5) . ?
C14B H14B 0.9300 . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
C16B C17B 1.506(5) . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
C19B H19D 0.9600 . ?
C19B H19E 0.9600 . ?
C19B H19F 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
C15 O2 C16 115.2(3) . . ?
C4 N1 C19 127.7(3) . . ?
C8 N1 C4 108.5(3) . . ?
C8 N1 C19 123.7(3) . . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 C15 120.1(3) . . ?
C6 C1 C15 118.5(3) . . ?
C1 C2 C3 117.0(3) . . ?
C1 C2 C18 124.6(3) . . ?
C3 C2 C18 118.4(3) . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 C7 132.1(3) . . ?
C4 C3 C7 107.0(3) . . ?
N1 C4 C3 107.1(3) . . ?
N1 C4 C5 131.2(3) . . ?
C5 C4 C3 121.6(3) . . ?
C4 C5 C9 124.1(3) . . ?
C6 C5 C4 116.1(3) . . ?
C6 C5 C9 119.7(3) . . ?
C1 C6 H6 118.7 . . ?
C5 C6 C1 122.6(3) . . ?
C5 C6 H6 118.7 . . ?
C3 C7 H7 126.8 . . ?
C8 C7 C3 106.4(3) . . ?
C8 C7 H7 126.8 . . ?
N1 C8 H8 124.5 . . ?
C7 C8 N1 111.0(3) . . ?
C7 C8 H8 124.5 . . ?
C10 C9 C5 121.8(3) . . ?
C10 C9 C14 118.4(3) . . ?
C14 C9 C5 119.8(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.9(3) . . ?
C13 C14 H14 119.6 . . ?
O1 C15 O2 121.8(3) . . ?
O1 C15 C1 125.7(3) . . ?
O2 C15 C1 112.5(3) . . ?
O2 C16 H16A 110.2 . . ?
O2 C16 H16B 110.2 . . ?
O2 C16 C17 107.8(3) . . ?
H16A C16 H16B 108.5 . . ?
C17 C16 H16A 110.2 . . ?
C17 C16 H16B 110.2 . . ?
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 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15B O2B C16B 116.2(3) . . ?
C4B N1B C19B 127.6(3) . . ?
C8B N1B C4B 108.8(3) . . ?
C8B N1B C19B 123.4(3) . . ?
C2B C1B C6B 120.8(3) . . ?
C2B C1B C15B 120.5(3) . . ?
C6B C1B C15B 118.7(3) . . ?
C1B C2B C3B 116.9(3) . . ?
C1B C2B C18B 124.3(3) . . ?
C3B C2B C18B 118.8(3) . . ?
C2B C3B C4B 121.3(3) . . ?
C2B C3B C7B 132.2(3) . . ?
C4B C3B C7B 106.4(3) . . ?
N1B C4B C3B 107.4(3) . . ?
N1B C4B C5B 131.1(3) . . ?
C5B C4B C3B 121.4(3) . . ?
C4B C5B C9B 124.7(3) . . ?
C6B C5B C4B 115.9(3) . . ?
C6B C5B C9B 119.3(3) . . ?
C1B C6B H6B 118.4 . . ?
C5B C6B C1B 123.2(3) . . ?
C5B C6B H6B 118.4 . . ?
C3B C7B H7B 126.4 . . ?
C8B C7B C3B 107.2(3) . . ?
C8B C7B H7B 126.4 . . ?
N1B C8B H8B 124.9 . . ?
C7B C8B N1B 110.2(3) . . ?
C7B C8B H8B 124.9 . . ?
C10B C9B C5B 120.1(3) . . ?
C10B C9B C14B 118.3(3) . . ?
C14B C9B C5B 121.5(3) . . ?
C9B C10B H10B 119.4 . . ?
C11B C10B C9B 121.2(3) . . ?
C11B C10B H10B 119.4 . . ?
C10B C11B H11B 120.1 . . ?
C12B C11B C10B 119.7(3) . . ?
C12B C11B H11B 120.1 . . ?
C11B C12B H12B 120.1 . . ?
C11B C12B C13B 119.7(3) . . ?
C13B C12B H12B 120.1 . . ?
C12B C13B H13B 119.9 . . ?
C14B C13B C12B 120.2(3) . . ?
C14B C13B H13B 119.9 . . ?
C9B C14B H14B 119.6 . . ?
C13B C14B C9B 120.9(3) . . ?
C13B C14B H14B 119.6 . . ?
O1B C15B O2B 122.1(3) . . ?
O1B C15B C1B 125.3(3) . . ?
O2B C15B C1B 112.5(3) . . ?
O2B C16B H16C 109.1 . . ?
O2B C16B H16D 109.1 . . ?
O2B C16B C17B 112.7(3) . . ?
H16C C16B H16D 107.8 . . ?
C17B C16B H16C 109.1 . . ?
C17B C16B H16D 109.1 . . ?
C16B C17B H17D 109.5 . . ?
C16B C17B H17E 109.5 . . ?
C16B C17B H17F 109.5 . . ?
H17D C17B H17E 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C2B C18B H18D 109.5 . . ?
C2B C18B H18E 109.5 . . ?
C2B C18B H18F 109.5 . . ?
H18D C18B H18E 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
N1B C19B H19D 109.5 . . ?
N1B C19B H19E 109.5 . . ?
N1B C19B H19F 109.5 . . ?
H19D C19B H19E 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 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
N1 C4 C5 C6 -174.2(3) . . . . ?
N1 C4 C5 C9 7.6(6) . . . . ?
C1 C2 C3 C4 -3.0(5) . . . . ?
C1 C2 C3 C7 174.7(4) . . . . ?
C2 C1 C6 C5 4.0(5) . . . . ?
C2 C1 C15 O1 -24.7(5) . . . . ?
C2 C1 C15 O2 154.6(3) . . . . ?
C2 C3 C4 N1 179.2(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C2 C3 C7 C8 -178.1(4) . . . . ?
C3 C4 C5 C6 5.1(5) . . . . ?
C3 C4 C5 C9 -173.2(3) . . . . ?
C3 C7 C8 N1 -0.9(4) . . . . ?
C4 N1 C8 C7 1.5(4) . . . . ?
C4 C3 C7 C8 -0.1(4) . . . . ?
C4 C5 C6 C1 -7.0(5) . . . . ?
C4 C5 C9 C10 -115.5(4) . . . . ?
C4 C5 C9 C14 66.9(5) . . . . ?
C5 C9 C10 C11 -178.7(3) . . . . ?
C5 C9 C14 C13 178.2(3) . . . . ?
C6 C1 C2 C3 1.2(5) . . . . ?
C6 C1 C2 C18 -178.5(3) . . . . ?
C6 C1 C15 O1 156.4(4) . . . . ?
C6 C1 C15 O2 -24.4(4) . . . . ?
C6 C5 C9 C10 66.3(5) . . . . ?
C6 C5 C9 C14 -111.3(4) . . . . ?
C7 C3 C4 N1 1.0(4) . . . . ?
C7 C3 C4 C5 -178.4(3) . . . . ?
C8 N1 C4 C3 -1.5(4) . . . . ?
C8 N1 C4 C5 177.8(3) . . . . ?
C9 C5 C6 C1 171.3(3) . . . . ?
C9 C10 C11 C12 1.2(6) . . . . ?
C10 C9 C14 C13 0.5(5) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C12 C13 C14 C9 -0.1(6) . . . . ?
C14 C9 C10 C11 -1.1(6) . . . . ?
C15 O2 C16 C17 177.5(3) . . . . ?
C15 C1 C2 C3 -177.6(3) . . . . ?
C15 C1 C2 C18 2.7(5) . . . . ?
C15 C1 C6 C5 -177.1(3) . . . . ?
C16 O2 C15 O1 2.2(5) . . . . ?
C16 O2 C15 C1 -177.0(3) . . . . ?
C18 C2 C3 C4 176.7(3) . . . . ?
C18 C2 C3 C7 -5.6(6) . . . . ?
C19 N1 C4 C3 -178.9(3) . . . . ?
C19 N1 C4 C5 0.4(6) . . . . ?
C19 N1 C8 C7 179.1(3) . . . . ?
N1B C4B C5B C6B -174.3(3) . . . . ?
N1B C4B C5B C9B 9.4(6) . . . . ?
C1B C2B C3B C4B -4.3(5) . . . . ?
C1B C2B C3B C7B 173.2(4) . . . . ?
C2B C1B C6B C5B 0.5(5) . . . . ?
C2B C1B C15B O1B -4.7(5) . . . . ?
C2B C1B C15B O2B 176.2(3) . . . . ?
C2B C3B C4B N1B 179.2(3) . . . . ?
C2B C3B C4B C5B -1.4(5) . . . . ?
C2B C3B C7B C8B -178.1(4) . . . . ?
C3B C4B C5B C6B 6.5(5) . . . . ?
C3B C4B C5B C9B -169.8(3) . . . . ?
C3B C7B C8B N1B -0.7(4) . . . . ?
C4B N1B C8B C7B 1.5(4) . . . . ?
C4B C3B C7B C8B -0.3(4) . . . . ?
C4B C5B C6B C1B -6.1(5) . . . . ?
C4B C5B C9B C10B 63.1(5) . . . . ?
C4B C5B C9B C14B -121.1(4) . . . . ?
C5B C9B C10B C11B 175.3(3) . . . . ?
C5B C9B C14B C13B -175.8(3) . . . . ?
C6B C1B C2B C3B 4.7(5) . . . . ?
C6B C1B C2B C18B -172.7(3) . . . . ?
C6B C1B C15B O1B 176.1(3) . . . . ?
C6B C1B C15B O2B -3.1(4) . . . . ?
C6B C5B C9B C10B -113.1(4) . . . . ?
C6B C5B C9B C14B 62.7(5) . . . . ?
C7B C3B C4B N1B 1.2(4) . . . . ?
C7B C3B C4B C5B -179.5(3) . . . . ?
C8B N1B C4B C3B -1.6(4) . . . . ?
C8B N1B C4B C5B 179.1(3) . . . . ?
C9B C5B C6B C1B 170.4(3) . . . . ?
C9B C10B C11B C12B 0.4(6) . . . . ?
C10B C9B C14B C13B 0.0(5) . . . . ?
C10B C11B C12B C13B 0.4(6) . . . . ?
C11B C12B C13B C14B -1.0(6) . . . . ?
C12B C13B C14B C9B 0.7(6) . . . . ?
C14B C9B C10B C11B -0.6(5) . . . . ?
C15B O2B C16B C17B 76.1(4) . . . . ?
C15B C1B C2B C3B -174.5(3) . . . . ?
C15B C1B C2B C18B 8.1(5) . . . . ?
C15B C1B C6B C5B 179.8(3) . . . . ?
C16B O2B C15B O1B -0.6(5) . . . . ?
C16B O2B C15B C1B 178.6(3) . . . . ?
C18B C2B C3B C4B 173.3(3) . . . . ?
C18B C2B C3B C7B -9.2(6) . . . . ?
C19B N1B C4B C3B -176.3(3) . . . . ?
C19B N1B C4B C5B 4.4(6) . . . . ?
C19B N1B C8B C7B 176.4(3) . . . . ?

_olex2_date_sample_data_collection 2019-05-20
_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 0.832
####################################################################### 
# 
# 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_indole1
_database_code_depnum_ccdc_archive 'CCDC 2131810'
loop_
_audit_author_name
_audit_author_address
CZY
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2021-12-30 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2019-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N O2'
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.2100(4)
_cell_length_b                   9.4039(6)
_cell_length_c                   10.1909(8)
_cell_angle_alpha                111.938(7)
_cell_angle_beta                 99.562(5)
_cell_angle_gamma                97.455(5)
_cell_volume                     703.68(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4157
_cell_measurement_temperature    293.75(10)
_cell_measurement_theta_max      28.8980
_cell_measurement_theta_min      2.3790
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.216
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.75(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  85.00   1.00    1.50    --   11.74  57.00 -60.00  101
  2  ω    -21.00  88.00   1.00    1.50    --   11.74  77.00  60.00  109
  3  ω    -60.00  40.00   1.00    1.50    --   11.74 -57.00 150.00  100
  4  ω     35.00 101.00   1.00    1.50    --   11.74 178.00 150.00   66
  5  ω    -16.00  23.00   1.00    1.50    --   11.74  57.00-180.00   39
  6  ω    -20.00  53.00   1.00    1.50    --   11.74 -99.00 -30.00   73
;
_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      -0.0890164000
_diffrn_orient_matrix_UB_12      -0.0165020000
_diffrn_orient_matrix_UB_13      -0.0255270000
_diffrn_orient_matrix_UB_21      -0.0099388000
_diffrn_orient_matrix_UB_22      0.0107366000
_diffrn_orient_matrix_UB_23      0.0706877000
_diffrn_orient_matrix_UB_31      0.0024793000
_diffrn_orient_matrix_UB_32      0.0807995000
_diffrn_orient_matrix_UB_33      0.0174906000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2148
_reflns_number_total             2474
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (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         0.190
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2474
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.043
_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)+(0.0512P)²+0.2297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1065
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C10(H10), C12(H12), C11(H11), C7(H7), C13(H13), C8(H8)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C)
;
_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
O2 O 0.68467(13) 0.02645(11) 0.21776(11) 0.0245(3) Uani 1 1 d . . . . .
O1 O 0.43700(14) -0.14253(13) 0.14497(13) 0.0355(3) Uani 1 1 d . . . . .
N1 N 0.35272(15) 0.41518(13) 0.71056(13) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.73544(17) 0.46487(16) 0.68519(15) 0.0164(3) Uani 1 1 d . . . . .
C4 C 0.59058(17) 0.33706(16) 0.58536(15) 0.0167(3) Uani 1 1 d . . . . .
C3 C 0.61512(18) 0.22334(16) 0.46134(15) 0.0182(3) Uani 1 1 d . . . . .
H3 H 0.722003 0.232306 0.442232 0.022 Uiso 1 1 calc R . . . .
C2 C 0.48727(18) 0.09421(16) 0.36185(15) 0.0184(3) Uani 1 1 d . . . . .
C1 C 0.32458(18) 0.07386(16) 0.38582(15) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.42487(18) 0.31895(16) 0.60724(15) 0.0173(3) Uani 1 1 d . . . . .
C14 C 0.78478(18) 0.49448(16) 0.83294(15) 0.0188(3) Uani 1 1 d . . . . .
H14 H 0.725568 0.433589 0.870563 0.023 Uiso 1 1 calc R . . . .
C10 C 0.82962(18) 0.55569(16) 0.63159(16) 0.0191(3) Uani 1 1 d . . . . .
H10 H 0.799939 0.536679 0.533498 0.023 Uiso 1 1 calc R . . . .
C12 C 1.01240(18) 0.70371(17) 0.86892(16) 0.0214(4) Uani 1 1 d . . . . .
H12 H 1.103774 0.783642 0.930146 0.026 Uiso 1 1 calc R . . . .
C11 C 0.96680(19) 0.67388(17) 0.72233(16) 0.0220(3) Uani 1 1 d . . . . .
H11 H 1.028446 0.733350 0.684866 0.026 Uiso 1 1 calc R . . . .
C17 C 0.52854(18) -0.01998(17) 0.23235(16) 0.0209(3) Uani 1 1 d . . . . .
C7 C 0.14568(18) 0.20789(17) 0.56330(16) 0.0198(3) Uani 1 1 d . . . . .
H7 H 0.040901 0.139343 0.523460 0.024 Uiso 1 1 calc R . . . .
C6 C 0.29608(18) 0.18806(16) 0.51110(15) 0.0174(3) Uani 1 1 d . . . . .
C13 C 0.92090(18) 0.61363(16) 0.92330(16) 0.0197(3) Uani 1 1 d . . . . .
H13 H 0.951152 0.633332 1.021522 0.024 Uiso 1 1 calc R . . . .
C16 C 0.17957(19) -0.05640(17) 0.28432(16) 0.0231(4) Uani 1 1 d . . . . .
H16A H 0.168067 -0.060405 0.187633 0.035 Uiso 1 1 calc GR . . . .
H16B H 0.077394 -0.037763 0.315645 0.035 Uiso 1 1 calc GR . . . .
H16C H 0.200504 -0.154328 0.284766 0.035 Uiso 1 1 calc GR . . . .
C8 C 0.18517(18) 0.34583(17) 0.68202(16) 0.0207(3) Uani 1 1 d . . . . .
H8 H 0.109521 0.387757 0.736584 0.025 Uiso 1 1 calc R . . . .
C15 C 0.42539(19) 0.57382(17) 0.81998(17) 0.0254(4) Uani 1 1 d . . . . .
H15A H 0.495162 0.568922 0.903041 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.336256 0.626076 0.849095 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.492562 0.630807 0.779778 0.038 Uiso 1 1 calc GR . . . .
C18 C 0.7329(2) -0.08257(18) 0.09579(17) 0.0275(4) Uani 1 1 d . . . . .
H18A H 0.661012 -0.092476 0.006988 0.041 Uiso 1 1 calc GR . . . .
H18B H 0.721838 -0.183015 0.101186 0.041 Uiso 1 1 calc GR . . . .
H18C H 0.848158 -0.044972 0.097823 0.041 Uiso 1 1 calc GR . . . .


_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
O2 C17 1.3500(18) . ?
O2 C18 1.4387(17) . ?
O1 C17 1.2133(18) . ?
N1 C5 1.3831(18) . ?
N1 C8 1.3765(19) . ?
N1 C15 1.4594(18) . ?
C9 C4 1.486(2) . ?
C9 C14 1.401(2) . ?
C9 C10 1.394(2) . ?
C4 C3 1.383(2) . ?
C4 C5 1.414(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.414(2) . ?
C2 C1 1.399(2) . ?
C2 C17 1.481(2) . ?
C1 C6 1.406(2) . ?
C1 C16 1.501(2) . ?
C5 C6 1.418(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.384(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.387(2) . ?
C12 C13 1.383(2) . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.430(2) . ?
C7 C8 1.356(2) . ?
C13 H13 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C8 H8 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C17 O2 C18 114.76(11) . . ?
C5 N1 C15 128.51(12) . . ?
C8 N1 C5 108.26(12) . . ?
C8 N1 C15 122.65(12) . . ?
C14 C9 C4 121.71(13) . . ?
C10 C9 C4 120.01(13) . . ?
C10 C9 C14 118.25(13) . . ?
C3 C4 C9 119.39(12) . . ?
C3 C4 C5 115.53(13) . . ?
C5 C4 C9 125.07(12) . . ?
C4 C3 H3 118.1 . . ?
C4 C3 C2 123.86(13) . . ?
C2 C3 H3 118.1 . . ?
C3 C2 C17 118.99(13) . . ?
C1 C2 C3 120.57(13) . . ?
C1 C2 C17 120.45(13) . . ?
C2 C1 C6 116.74(13) . . ?
C2 C1 C16 124.41(13) . . ?
C6 C1 C16 118.80(13) . . ?
N1 C5 C4 131.08(13) . . ?
N1 C5 C6 107.38(12) . . ?
C4 C5 C6 121.49(13) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.51(14) . . ?
C13 C14 H14 119.7 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.97(13) . . ?
C11 C10 H10 119.5 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C13 C12 C11 119.48(14) . . ?
C10 C11 C12 120.15(14) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
O2 C17 C2 112.53(12) . . ?
O1 C17 O2 121.16(13) . . ?
O1 C17 C2 126.31(14) . . ?
C6 C7 H7 126.6 . . ?
C8 C7 H7 126.6 . . ?
C8 C7 C6 106.86(13) . . ?
C1 C6 C5 121.74(13) . . ?
C1 C6 C7 131.24(13) . . ?
C5 C6 C7 106.87(12) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 C14 120.62(14) . . ?
C12 C13 H13 119.7 . . ?
C1 C16 H16A 109.5 . . ?
C1 C16 H16B 109.5 . . ?
C1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C8 H8 124.7 . . ?
C7 C8 N1 110.61(13) . . ?
C7 C8 H8 124.7 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.566
_oxdiff_exptl_absorpt_empirical_full_min 0.737
####################################################################### 
# 
# 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_indole2
_database_code_depnum_ccdc_archive 'CCDC 2131811'
loop_
_audit_author_name
_audit_author_address
CZY
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2021-12-30 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2019-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N O2'
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.7113(6)
_cell_length_b                   9.8511(5)
_cell_length_c                   25.2850(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.144(5)
_cell_angle_gamma                90
_cell_volume                     2894.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5197
_cell_measurement_temperature    293.75(10)
_cell_measurement_theta_max      28.6730
_cell_measurement_theta_min      2.7900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14067
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.021
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.75(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  58.00   1.00    4.00    --  -11.59  57.00 -60.00   89
  2  ω     47.00  85.00   1.00    4.00    --   11.74  37.00-180.00   38
  3  ω     41.00  96.00   1.00    4.00    --   11.74 178.00-180.00   55
  4  ω    -20.00  22.00   1.00    4.00    --  -11.59 -99.00 120.00   42
;
_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      -0.0091647000
_diffrn_orient_matrix_UB_12      -0.0699451000
_diffrn_orient_matrix_UB_13      -0.0056358000
_diffrn_orient_matrix_UB_21      -0.0564181000
_diffrn_orient_matrix_UB_22      0.0051390000
_diffrn_orient_matrix_UB_23      0.0073186000
_diffrn_orient_matrix_UB_31      -0.0215023000
_diffrn_orient_matrix_UB_32      0.0162401000
_diffrn_orient_matrix_UB_33      -0.0267077000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4201
_reflns_number_total             5094
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (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         0.262
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5094
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.013
_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)+(0.0573P)²+1.3803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1250
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C12B(H12B), C2(H2), C7B(H7B), C16B(H16B), C7(H7), C16(H16),
 C12(H12), C13B(H13B), C14B(H14B), C13(H13), C8B(H8B), C15B(H15B), C14(H14),
 C15(H15), C8(H8)
2.b Idealised Me refined as rotating group:
 C10B(H10D,H10E,H10F), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C9B(H9BA,H9BB,
 H9BC), C18(H18A,H18B,H18C), C18B(H18D,H18E,H18F)
;
_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 0.42823(11) 0.15174(14) 0.69822(5) 0.0367(4) Uani 1 1 d . . . . .
O2B O 0.33524(11) 0.40306(15) 0.55535(5) 0.0375(4) Uani 1 1 d . . . . .
O2 O 0.53859(12) 0.16623(15) 0.63209(6) 0.0426(4) Uani 1 1 d . . . . .
O1B O 0.22600(11) 0.39450(15) 0.62200(6) 0.0412(4) Uani 1 1 d . . . . .
N1B N 0.46335(13) 0.80906(16) 0.73005(6) 0.0298(4) Uani 1 1 d . . . . .
N1 N 0.30387(14) -0.24912(16) 0.52217(6) 0.0309(4) Uani 1 1 d . . . . .
C1 C 0.16001(15) -0.02387(18) 0.60448(7) 0.0251(4) Uani 1 1 d . . . . .
C11B C 0.72444(15) 0.55510(19) 0.63681(7) 0.0239(4) Uani 1 1 d . . . . .
C5B C 0.57871(15) 0.68599(19) 0.68299(7) 0.0241(4) Uani 1 1 d . . . . .
C4B C 0.60489(15) 0.58259(18) 0.64754(7) 0.0231(4) Uani 1 1 d . . . . .
C6B C 0.46279(15) 0.70424(19) 0.69312(7) 0.0251(4) Uani 1 1 d . . . . .
C5 C 0.30305(16) -0.14158(19) 0.55766(7) 0.0261(4) Uani 1 1 d . . . . .
C1B C 0.36983(15) 0.62809(19) 0.66786(7) 0.0253(4) Uani 1 1 d . . . . .
C2B C 0.39964(15) 0.52783(19) 0.63269(7) 0.0255(4) Uani 1 1 d . . . . .
C11 C 0.04139(15) -0.00174(18) 0.61736(7) 0.0253(4) Uani 1 1 d . . . . .
C3B C 0.51430(15) 0.50615(19) 0.62325(7) 0.0248(4) Uani 1 1 d . . . . .
H3B H 0.529566 0.437761 0.599766 0.030 Uiso 1 1 calc R . . . .
C12B C 0.76346(15) 0.42195(19) 0.63192(7) 0.0261(4) Uani 1 1 d . . . . .
H12B H 0.714250 0.349631 0.635973 0.031 Uiso 1 1 calc R . . . .
C4 C 0.39515(16) -0.06470(19) 0.58339(7) 0.0277(4) Uani 1 1 d . . . . .
C2 C 0.25079(15) 0.04993(19) 0.63018(7) 0.0266(4) Uani 1 1 d . . . . .
H2 H 0.235679 0.114304 0.655300 0.032 Uiso 1 1 calc R . . . .
C3 C 0.36541(15) 0.03167(19) 0.61990(7) 0.0267(4) Uani 1 1 d . . . . .
C6 C 0.18707(15) -0.12287(19) 0.56738(7) 0.0257(4) Uani 1 1 d . . . . .
C17B C 0.31029(15) 0.4364(2) 0.60434(8) 0.0292(4) Uani 1 1 d . . . . .
C7B C 0.64639(16) 0.7830(2) 0.71452(7) 0.0291(4) Uani 1 1 d . . . . .
H7B H 0.725438 0.795513 0.716004 0.035 Uiso 1 1 calc R . . . .
C16B C 0.80094(16) 0.6607(2) 0.63071(7) 0.0298(4) Uani 1 1 d . . . . .
H16B H 0.776839 0.750003 0.633691 0.036 Uiso 1 1 calc R . . . .
C7 C 0.11997(17) -0.2228(2) 0.53702(7) 0.0307(4) Uani 1 1 d . . . . .
H7 H 0.040939 -0.235576 0.535444 0.037 Uiso 1 1 calc R . . . .
C17 C 0.45377(16) 0.12191(19) 0.64898(8) 0.0299(4) Uani 1 1 d . . . . .
C16 C 0.02047(16) 0.01476(19) 0.67008(7) 0.0284(4) Uani 1 1 d . . . . .
H16 H 0.081643 0.011287 0.697284 0.034 Uiso 1 1 calc R . . . .
C12 C -0.05307(16) 0.0040(2) 0.57764(7) 0.0305(4) Uani 1 1 d . . . . .
H12 H -0.041652 -0.007362 0.542158 0.037 Uiso 1 1 calc R . . . .
C13B C 0.87457(15) 0.3967(2) 0.62112(7) 0.0288(4) Uani 1 1 d . . . . .
H13B H 0.899244 0.307737 0.617823 0.035 Uiso 1 1 calc R . . . .
C14B C 0.94912(16) 0.5031(2) 0.61519(7) 0.0323(5) Uani 1 1 d . . . . .
H14B H 1.023622 0.485940 0.607827 0.039 Uiso 1 1 calc R . . . .
C13 C -0.16316(16) 0.0262(2) 0.59029(8) 0.0334(5) Uani 1 1 d . . . . .
H13 H -0.224780 0.030354 0.563321 0.040 Uiso 1 1 calc R . . . .
C8B C 0.57398(17) 0.8538(2) 0.74198(7) 0.0326(5) Uani 1 1 d . . . . .
H8B H 0.596557 0.923519 0.765784 0.039 Uiso 1 1 calc R . . . .
C15B C 0.91197(16) 0.6350(2) 0.62031(7) 0.0331(5) Uani 1 1 d . . . . .
H15B H 0.961943 0.706811 0.616736 0.040 Uiso 1 1 calc R . . . .
C14 C -0.18196(17) 0.04239(19) 0.64279(8) 0.0333(5) Uani 1 1 d . . . . .
H14 H -0.255954 0.057281 0.651284 0.040 Uiso 1 1 calc R . . . .
C15 C -0.08982(16) 0.0362(2) 0.68259(8) 0.0324(5) Uani 1 1 d . . . . .
H15 H -0.102039 0.046551 0.718010 0.039 Uiso 1 1 calc R . . . .
C8 C 0.19347(17) -0.2959(2) 0.51086(7) 0.0335(5) Uani 1 1 d . . . . .
H8 H 0.171729 -0.368224 0.488204 0.040 Uiso 1 1 calc R . . . .
C10B C 0.24722(16) 0.6595(2) 0.67572(8) 0.0339(5) Uani 1 1 d . . . . .
H10D H 0.231486 0.623934 0.709410 0.051 Uiso 1 1 calc GR . . . .
H10E H 0.196064 0.618570 0.647582 0.051 Uiso 1 1 calc GR . . . .
H10F H 0.235939 0.756048 0.675164 0.051 Uiso 1 1 calc GR . . . .
C10 C 0.51859(16) -0.0910(2) 0.57432(8) 0.0355(5) Uani 1 1 d . . . . .
H10A H 0.533599 -0.186812 0.576179 0.053 Uiso 1 1 calc GR . . . .
H10B H 0.569556 -0.045215 0.601220 0.053 Uiso 1 1 calc GR . . . .
H10C H 0.530892 -0.057711 0.539794 0.053 Uiso 1 1 calc GR . . . .
C9 C 0.39843(18) -0.3065(2) 0.49692(8) 0.0407(5) Uani 1 1 d . . . . .
H9A H 0.431841 -0.237123 0.477071 0.061 Uiso 1 1 calc GR . . . .
H9B H 0.369821 -0.378445 0.473276 0.061 Uiso 1 1 calc GR . . . .
H9C H 0.455840 -0.341847 0.523815 0.061 Uiso 1 1 calc GR . . . .
C9B C 0.37045(18) 0.8587(2) 0.75834(8) 0.0402(5) Uani 1 1 d . . . . .
H9BA H 0.315987 0.908028 0.734100 0.060 Uiso 1 1 calc GR . . . .
H9BB H 0.401565 0.917501 0.786816 0.060 Uiso 1 1 calc GR . . . .
H9BC H 0.332655 0.783176 0.772732 0.060 Uiso 1 1 calc GR . . . .
C18 C 0.5075(2) 0.2417(2) 0.72930(9) 0.0481(6) Uani 1 1 d . . . . .
H18A H 0.504553 0.329685 0.712889 0.072 Uiso 1 1 calc GR . . . .
H18B H 0.584092 0.205917 0.730984 0.072 Uiso 1 1 calc GR . . . .
H18C H 0.486479 0.249226 0.764691 0.072 Uiso 1 1 calc GR . . . .
C18B C 0.2552(2) 0.3128(2) 0.52472(9) 0.0493(6) Uani 1 1 d . . . . .
H18D H 0.280215 0.296748 0.490526 0.074 Uiso 1 1 calc GR . . . .
H18E H 0.180102 0.353419 0.519968 0.074 Uiso 1 1 calc GR . . . .
H18F H 0.252049 0.228167 0.543333 0.074 Uiso 1 1 calc GR . . . .


_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 C17 1.349(2) . ?
O1 C18 1.443(2) . ?
O2B C17B 1.348(2) . ?
O2B C18B 1.446(2) . ?
O2 C17 1.210(2) . ?
O1B C17B 1.206(2) . ?
N1B C6B 1.392(2) . ?
N1B C8B 1.366(2) . ?
N1B C9B 1.459(2) . ?
N1 C5 1.389(2) . ?
N1 C8 1.369(2) . ?
N1 C9 1.459(2) . ?
C1 C11 1.482(2) . ?
C1 C2 1.382(3) . ?
C1 C6 1.416(3) . ?
C11B C4B 1.484(2) . ?
C11B C12B 1.399(3) . ?
C11B C16B 1.394(3) . ?
C5B C4B 1.415(3) . ?
C5B C6B 1.424(2) . ?
C5B C7B 1.421(3) . ?
C4B C3B 1.381(2) . ?
C6B C1B 1.408(3) . ?
C5 C4 1.409(3) . ?
C5 C6 1.422(3) . ?
C1B C2B 1.402(3) . ?
C1B C10B 1.506(2) . ?
C2B C3B 1.409(2) . ?
C2B C17B 1.494(3) . ?
C11 C16 1.395(3) . ?
C11 C12 1.400(3) . ?
C3B H3B 0.9300 . ?
C12B H12B 0.9300 . ?
C12B C13B 1.385(2) . ?
C4 C3 1.398(3) . ?
C4 C10 1.514(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.410(2) . ?
C3 C17 1.487(3) . ?
C6 C7 1.423(3) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.354(3) . ?
C16B H16B 0.9300 . ?
C16B C15B 1.382(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.356(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(3) . ?
C13B H13B 0.9300 . ?
C13B C14B 1.384(3) . ?
C14B H14B 0.9300 . ?
C14B C15B 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(3) . ?
C8B H8B 0.9300 . ?
C15B H15B 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.382(3) . ?
C15 H15 0.9300 . ?
C8 H8 0.9300 . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 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
C17 O1 C18 115.79(16) . . ?
C17B O2B C18B 116.24(16) . . ?
C6B N1B C9B 129.51(17) . . ?
C8B N1B C6B 108.21(15) . . ?
C8B N1B C9B 121.90(16) . . ?
C5 N1 C9 130.15(17) . . ?
C8 N1 C5 108.01(16) . . ?
C8 N1 C9 121.78(17) . . ?
C2 C1 C11 120.45(16) . . ?
C2 C1 C6 116.83(16) . . ?
C6 C1 C11 122.69(16) . . ?
C12B C11B C4B 120.87(16) . . ?
C16B C11B C4B 121.21(17) . . ?
C16B C11B C12B 117.92(17) . . ?
C4B C5B C6B 119.42(16) . . ?
C4B C5B C7B 133.59(16) . . ?
C7B C5B C6B 106.98(16) . . ?
C5B C4B C11B 122.06(15) . . ?
C3B C4B C11B 120.61(16) . . ?
C3B C4B C5B 117.33(16) . . ?
N1B C6B C5B 106.82(16) . . ?
N1B C6B C1B 129.67(16) . . ?
C1B C6B C5B 123.49(16) . . ?
N1 C5 C4 129.92(17) . . ?
N1 C5 C6 107.10(16) . . ?
C4 C5 C6 122.90(17) . . ?
C6B C1B C10B 121.79(17) . . ?
C2B C1B C6B 115.06(16) . . ?
C2B C1B C10B 123.03(17) . . ?
C1B C2B C3B 122.14(17) . . ?
C1B C2B C17B 120.93(16) . . ?
C3B C2B C17B 116.92(16) . . ?
C16 C11 C1 120.55(16) . . ?
C16 C11 C12 117.65(17) . . ?
C12 C11 C1 121.80(16) . . ?
C4B C3B C2B 122.52(17) . . ?
C4B C3B H3B 118.7 . . ?
C2B C3B H3B 118.7 . . ?
C11B C12B H12B 119.6 . . ?
C13B C12B C11B 120.71(17) . . ?
C13B C12B H12B 119.6 . . ?
C5 C4 C10 121.90(17) . . ?
C3 C4 C5 115.50(16) . . ?
C3 C4 C10 122.50(17) . . ?
C1 C2 H2 118.6 . . ?
C1 C2 C3 122.72(17) . . ?
C3 C2 H2 118.6 . . ?
C4 C3 C2 121.96(17) . . ?
C4 C3 C17 121.14(16) . . ?
C2 C3 C17 116.89(17) . . ?
C1 C6 C5 120.07(16) . . ?
C1 C6 C7 132.81(17) . . ?
C7 C6 C5 106.99(16) . . ?
O2B C17B C2B 111.64(16) . . ?
O1B C17B O2B 122.52(18) . . ?
O1B C17B C2B 125.83(18) . . ?
C5B C7B H7B 126.5 . . ?
C8B C7B C5B 107.01(17) . . ?
C8B C7B H7B 126.5 . . ?
C11B C16B H16B 119.4 . . ?
C15B C16B C11B 121.15(19) . . ?
C15B C16B H16B 119.4 . . ?
C6 C7 H7 126.6 . . ?
C8 C7 C6 106.79(17) . . ?
C8 C7 H7 126.6 . . ?
O1 C17 C3 111.47(16) . . ?
O2 C17 O1 122.21(18) . . ?
O2 C17 C3 126.31(18) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 121.08(17) . . ?
C15 C16 H16 119.5 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.09(18) . . ?
C13 C12 H12 119.5 . . ?
C12B C13B H13B 119.8 . . ?
C12B C13B C14B 120.42(18) . . ?
C14B C13B H13B 119.8 . . ?
C13B C14B H14B 120.3 . . ?
C15B C14B C13B 119.45(17) . . ?
C15B C14B H14B 120.3 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.31(18) . . ?
C14 C13 H13 119.8 . . ?
N1B C8B H8B 124.5 . . ?
C7B C8B N1B 110.98(17) . . ?
C7B C8B H8B 124.5 . . ?
C16B C15B H15B 119.8 . . ?
C14B C15B C16B 120.35(18) . . ?
C14B C15B H15B 119.8 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.42(18) . . ?
C15 C14 H14 120.3 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.45(18) . . ?
C14 C15 H15 119.8 . . ?
N1 C8 H8 124.4 . . ?
C7 C8 N1 111.11(18) . . ?
C7 C8 H8 124.4 . . ?
C1B C10B H10D 109.5 . . ?
C1B C10B H10E 109.5 . . ?
C1B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1B C9B H9BA 109.5 . . ?
N1B C9B H9BB 109.5 . . ?
N1B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2B C18B H18D 109.5 . . ?
O2B C18B H18E 109.5 . . ?
O2B C18B H18F 109.5 . . ?
H18D C18B H18E 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?

_olex2_date_sample_data_collection 2019-01-25
_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 1.473
_oxdiff_exptl_absorpt_empirical_full_min 0.740
####################################################################### 
# 
# 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_c2y-b
_database_code_depnum_ccdc_archive 'CCDC 2131809'
loop_
_audit_author_name
_audit_author_address
CZY
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2021-12-30 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2019-05-29
_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         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_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                   12.6474(9)
_cell_length_b                   7.3679(5)
_cell_length_c                   17.5437(13)
_cell_angle_alpha                90
_cell_angle_beta                 110.655(9)
_cell_angle_gamma                90
_cell_volume                     1529.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2583
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.3340
_cell_measurement_theta_min      3.7120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6302
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.501
_diffrn_reflns_theta_min         3.756
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  45.00   1.00    2.29    --   40.98 -38.00 120.00   43
  2  ω     23.00  69.00   1.00    2.29    --   40.98-125.00  30.00   46
  3  ω     36.00 135.00   1.00    4.00    --  106.95 -61.00 150.00   99
  4  ω    134.00 166.00   1.00    4.00    --  106.95  15.00   0.00   32
  5  ω     77.00 107.00   1.00    4.00    --  106.95-125.00 -60.00   30
  6  ω     34.00 114.00   1.00    4.00    --  106.95-125.00 120.00   80
  7  ω     55.00  86.00   1.00    4.00    --  106.95  15.00   0.00   31
  8  ω    -95.00 -18.00   1.00    2.29    --  -40.98 -57.00-120.00   77
  9  ω   -111.00 -23.00   1.00    2.29    --  -41.23 -39.00 134.00   88
 10  ω     23.00  48.00   1.00    2.29    --   41.23-125.00 -30.00   25
 11  ω     55.00  81.00   1.00    2.29    --   41.23-125.00 -30.00   26
 12  ω     99.00 128.00   1.00    4.00    --  106.95 -30.00 -90.00   29
 13  ω     41.00  82.00   1.00    4.00    --  106.95 -30.00 -90.00   41
 14  ω     85.00 164.00   1.00    4.00    --  106.95  61.00 -60.00   79
 15  ω     41.00  67.00   1.00    4.00    --  106.95 -77.00  60.00   26
;
_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      -0.0165832000
_diffrn_orient_matrix_UB_12      0.0888121000
_diffrn_orient_matrix_UB_13      -0.0827810000
_diffrn_orient_matrix_UB_21      -0.1211532000
_diffrn_orient_matrix_UB_22      0.0540606000
_diffrn_orient_matrix_UB_23      -0.0083104000
_diffrn_orient_matrix_UB_31      0.0445237000
_diffrn_orient_matrix_UB_32      0.1813832000
_diffrn_orient_matrix_UB_33      0.0434166000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                2422
_reflns_number_total             2986
_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 (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         0.234
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.052
_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     202
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0474
_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)+(0.0560P)²+0.4510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1276
_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:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C10(H10), C7(H7), C11(H11), C8(H8), C13(H13), C12(H12)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
;
_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
O2 O 0.20352(10) 0.50182(17) 0.31829(8) 0.0262(3) Uani 1 1 d . . . . .
O1 O 0.18528(10) 0.22334(16) 0.36488(8) 0.0258(3) Uani 1 1 d . . . . .
N1 N 0.63029(12) 0.19284(19) 0.55327(8) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.36967(14) 0.3263(2) 0.38337(10) 0.0201(4) Uani 1 1 d . . . . .
C9 C 0.58273(14) 0.3332(2) 0.27606(10) 0.0204(4) Uani 1 1 d . . . . .
C6 C 0.54672(14) 0.2455(2) 0.48105(10) 0.0197(4) Uani 1 1 d . . . . .
C3 C 0.42032(15) 0.3452(2) 0.32394(10) 0.0209(4) Uani 1 1 d . . . . .
H3 H 0.375669 0.379571 0.271419 0.025 Uiso 1 1 calc R . . . .
C5 C 0.59942(14) 0.2649(2) 0.42200(10) 0.0200(4) Uani 1 1 d . . . . .
C1 C 0.43061(15) 0.2778(2) 0.46374(10) 0.0208(4) Uani 1 1 d . . . . .
C4 C 0.53397(15) 0.3144(2) 0.34121(10) 0.0201(4) Uani 1 1 d . . . . .
C14 C 0.52611(15) 0.2594(2) 0.19922(10) 0.0219(4) Uani 1 1 d . . . . .
H14 H 0.459453 0.195044 0.189876 0.026 Uiso 1 1 calc R . . . .
C15 C 0.24602(15) 0.3644(2) 0.35339(10) 0.0202(4) Uani 1 1 d . . . . .
C10 C 0.68320(15) 0.4287(2) 0.28877(11) 0.0241(4) Uani 1 1 d . . . . .
H10 H 0.722298 0.478861 0.339588 0.029 Uiso 1 1 calc R . . . .
C7 C 0.71619(15) 0.2234(2) 0.46151(11) 0.0227(4) Uani 1 1 d . . . . .
H7 H 0.771875 0.225103 0.438268 0.027 Uiso 1 1 calc R . . . .
C11 C 0.72481(16) 0.4489(3) 0.22560(12) 0.0280(4) Uani 1 1 d . . . . .
H11 H 0.791524 0.512834 0.234571 0.034 Uiso 1 1 calc R . . . .
C8 C 0.73010(15) 0.1809(2) 0.54007(11) 0.0236(4) Uani 1 1 d . . . . .
H8 H 0.798608 0.147996 0.579481 0.028 Uiso 1 1 calc R . . . .
C18 C 0.37653(15) 0.2707(2) 0.52772(10) 0.0234(4) Uani 1 1 d . . . . .
H18A H 0.304505 0.330486 0.507723 0.035 Uiso 1 1 calc GR . . . .
H18B H 0.424421 0.330648 0.576182 0.035 Uiso 1 1 calc GR . . . .
H18C H 0.366236 0.146412 0.539993 0.035 Uiso 1 1 calc GR . . . .
C13 C 0.56813(16) 0.2808(2) 0.13637(11) 0.0258(4) Uani 1 1 d . . . . .
H13 H 0.529116 0.231931 0.085268 0.031 Uiso 1 1 calc R . . . .
C19 C 0.62066(16) 0.1497(2) 0.63184(10) 0.0244(4) Uani 1 1 d . . . . .
H19A H 0.611849 0.259799 0.658229 0.037 Uiso 1 1 calc GR . . . .
H19B H 0.687678 0.087723 0.665437 0.037 Uiso 1 1 calc GR . . . .
H19C H 0.556127 0.073083 0.623492 0.037 Uiso 1 1 calc GR . . . .
C12 C 0.66813(17) 0.3750(3) 0.14977(11) 0.0287(4) Uani 1 1 d . . . . .
H12 H 0.696751 0.388231 0.107997 0.034 Uiso 1 1 calc R . . . .
C16 C 0.06386(15) 0.2478(3) 0.33935(12) 0.0284(4) Uani 1 1 d . . . . .
H16A H 0.025823 0.136040 0.315725 0.034 Uiso 1 1 calc R . . . .
H16B H 0.039892 0.342108 0.298220 0.034 Uiso 1 1 calc R . . . .
C17 C 0.03248(19) 0.2997(3) 0.41131(13) 0.0402(5) Uani 1 1 d . . . . .
H17A H -0.047772 0.317087 0.394088 0.060 Uiso 1 1 calc GR . . . .
H17B H 0.070285 0.410359 0.434514 0.060 Uiso 1 1 calc GR . . . .
H17C H 0.054861 0.204903 0.451362 0.060 Uiso 1 1 calc GR . . . .


_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
O2 C15 1.208(2) . ?
O1 C15 1.349(2) . ?
O1 C16 1.451(2) . ?
N1 C6 1.389(2) . ?
N1 C8 1.364(2) . ?
N1 C19 1.461(2) . ?
C2 C3 1.410(2) . ?
C2 C1 1.394(2) . ?
C2 C15 1.490(2) . ?
C9 C4 1.484(2) . ?
C9 C14 1.395(2) . ?
C9 C10 1.400(2) . ?
C6 C5 1.423(2) . ?
C6 C1 1.411(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(2) . ?
C5 C4 1.414(2) . ?
C5 C7 1.426(2) . ?
C1 C18 1.507(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.392(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.392(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.363(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(3) . ?
C8 H8 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C12 1.388(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C12 H12 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.500(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C15 O1 C16 117.03(14) . . ?
C6 N1 C19 129.18(15) . . ?
C8 N1 C6 108.37(14) . . ?
C8 N1 C19 122.43(14) . . ?
C3 C2 C15 114.48(15) . . ?
C1 C2 C3 122.68(16) . . ?
C1 C2 C15 122.84(15) . . ?
C14 C9 C4 119.78(15) . . ?
C14 C9 C10 118.55(16) . . ?
C10 C9 C4 121.65(15) . . ?
N1 C6 C5 106.92(15) . . ?
N1 C6 C1 130.01(16) . . ?
C1 C6 C5 123.07(15) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.10(16) . . ?
C4 C3 H3 118.9 . . ?
C6 C5 C7 107.19(15) . . ?
C4 C5 C6 119.78(16) . . ?
C4 C5 C7 133.02(16) . . ?
C2 C1 C6 115.03(16) . . ?
C2 C1 C18 121.87(16) . . ?
C6 C1 C18 123.03(16) . . ?
C3 C4 C9 119.96(15) . . ?
C3 C4 C5 117.31(16) . . ?
C5 C4 C9 122.73(16) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.81(17) . . ?
C13 C14 H14 119.6 . . ?
O2 C15 O1 123.18(16) . . ?
O2 C15 C2 124.09(15) . . ?
O1 C15 C2 112.59(14) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.24(17) . . ?
C11 C10 H10 119.9 . . ?
C5 C7 H7 126.8 . . ?
C8 C7 C5 106.43(16) . . ?
C8 C7 H7 126.8 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.73(17) . . ?
C12 C11 H11 119.6 . . ?
N1 C8 H8 124.5 . . ?
C7 C8 N1 111.08(15) . . ?
C7 C8 H8 124.5 . . ?
C1 C18 H18A 109.5 . . ?
C1 C18 H18B 109.5 . . ?
C1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.15(17) . . ?
C12 C13 H13 119.9 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C12 C13 119.52(17) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
O1 C16 H16A 109.7 . . ?
O1 C16 H16B 109.7 . . ?
O1 C16 C17 109.70(16) . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
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 . . ?

_olex2_date_sample_data_collection 2019-05-29
_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 1.345
_oxdiff_exptl_absorpt_empirical_full_min 0.619
