# 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_exp_3599
_database_code_depnum_ccdc_archive 'CCDC 2213238'
loop_
_audit_author_name
_audit_author_address
'Jian-Liang Ye'
;College of Chemistry and Chemical Engineering, Xiamen University
China
;
_audit_update_record             
;
2022-10-16 deposited with the CCDC.	2023-03-05 downloaded from the CCDC.
;
_audit_creation_date             2022-10-16
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C16 H19 N O2'
_chemical_formula_sum            'C16 H19 N O2'
_chemical_formula_weight         257.335
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.96411(10)
_cell_length_b                   13.49912(14)
_cell_length_c                   12.50563(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.1964(13)
_cell_angle_gamma                90
_cell_volume                     1308.96(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7001
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.7390
_cell_measurement_theta_min      4.8900
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             553.778
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.9945
_diffrn_reflns_Laue_measured_fraction_max 0.9726
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12781
_diffrn_reflns_point_group_measured_fraction_full 0.9945
_diffrn_reflns_point_group_measured_fraction_max 0.9726
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         71.76
_diffrn_reflns_theta_min         4.89
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9945
_diffrn_measured_fraction_theta_max 0.9726
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     80.00 139.00   0.50    0.12    --  102.25  45.00 -60.00  118
  2  ω    153.00 178.00   0.50    0.12    --  102.25  45.00 -60.00   50
  3  ω    102.00 173.00   0.50    0.12    --  102.25  45.00  30.00  142
  4  ω    103.00 129.00   0.50    0.12    --  102.25  30.00  60.00   52
  5  ω    137.00 171.00   0.50    0.12    --  102.25  30.00  60.00   68
  6  ω    -65.00 -23.00   0.50    0.12    --  -90.25 125.00  60.00   84
  7  ω    -90.00 -24.00   0.50    0.12    --  -90.25 125.00   0.00  132
  8  ω    -88.00 -50.00   0.50    0.12    --  -90.25 125.00 -60.00   76
  9  ω    -91.00 -43.00   0.50    0.12    --  -90.25 125.00-120.00   96
 10  ω   -102.00 -66.00   0.50    0.12    --  -90.25  77.00   0.00   72
 11  ω    -21.00  37.00   0.50    0.05    --  -43.10  19.00  60.00  116
 12  ω    -42.00  34.00   0.50    0.05    --  -43.10  38.00 -60.00  152
 13  ω    -40.00 -15.00   0.50    0.12    --  -90.25  45.00 -90.00   50
 14  ω    -48.00 -16.00   0.50    0.12    --  -90.25  45.00 -30.00   64
 15  ω    -60.00 -16.00   0.50    0.12    --  -90.25  61.00  90.00   88
 16  ω   -166.00 -65.00   0.50    0.12    --  -90.25 -45.00 -30.00  202
 17  ω   -116.00 -25.00   0.50    0.05    --  -43.10 -57.00 150.00  182
 18  ω   -144.00 -65.00   0.50    0.12    --  -90.25 -61.00-180.00  158
 19  ω   -165.00 -67.00   0.50    0.12    --  -90.25 -45.00-150.00  196
 20  ω   -112.00 -87.00   0.50    0.05    --  -43.10-125.00-180.00   50
 21  ω   -116.00 -91.00   0.50    0.05    --  -43.10-125.00 -30.00   50
 22  ω     35.00  83.00   0.50    0.12    --  102.25 -77.00 150.00   96
 23  ω     30.00  70.00   0.50    0.12    --  102.25 -61.00  90.00   80
 24  ω    127.00 167.00   0.50    0.12    --  102.25 125.00-150.00   80
 25  ω     44.00  69.00   0.50    0.12    --  102.25 -61.00 -30.00   50
 26  ω     74.00 105.00   0.50    0.12    --  102.25 -77.00-180.00   62
 27  ω     32.00  67.00   0.50    0.12    --  102.25 -77.00-180.00   70
 28  ω     43.00  72.00   0.50    0.05    --   43.10 -99.00 -60.00   58
 29  ω     78.00 123.00   0.50    0.12    --  102.25-134.00 104.36   90
 30  ω     60.00 117.00   0.50    0.12    --  102.25-125.00   0.00  114
 31  ω     68.00 113.00   0.50    0.12    --  102.25-125.00-120.00   90
 32  ω     39.00 110.00   0.50    0.12    --  102.25-125.00-180.00  142
 33  ω     -4.00  26.00   0.50    0.05    --   43.10 -99.00 -60.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1582226000
_diffrn_orient_matrix_UB_12      -0.0265624000
_diffrn_orient_matrix_UB_13      0.0456961000
_diffrn_orient_matrix_UB_21      -0.0884190000
_diffrn_orient_matrix_UB_22      -0.0454223000
_diffrn_orient_matrix_UB_23      -0.1117324000
_diffrn_orient_matrix_UB_31      0.0813423000
_diffrn_orient_matrix_UB_32      -0.1012318000
_diffrn_orient_matrix_UB_33      0.0381047000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2347
_reflns_number_total             2487
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_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  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.2348
_refine_diff_density_min         -0.3013
_refine_diff_density_rms         0.0646
_refine_ls_d_res_high            0.8117
_refine_ls_d_res_low             9.0412
_refine_ls_goodness_of_fit_ref   1.0528
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.0528
_refine_ls_shift/su_max          -0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.4965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0941
_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:
 C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C8(H8a,H8b), C15(H15a,H15b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C14(H14a,H14b,H14c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O1 O 0.74903(10) 0.21419(6) 0.54159(6) 0.0184(2) Uani 1.000000 .
O2 O 0.79604(9) 0.05981(5) 0.27103(6) 0.01410(19) Uani 1.000000 .
N2 N 0.74654(11) 0.21251(6) 0.35804(7) 0.0130(2) Uani 1.000000 .
C C 0.73928(13) 0.16772(8) 0.45530(8) 0.0133(2) Uani 1.000000 .
C1 C 0.77488(13) 0.01357(8) 0.36350(9) 0.0133(2) Uani 1.000000 .
C2 C 0.21728(15) 0.13993(8) 0.20287(10) 0.0184(2) Uani 1.000000 .
H2 H 0.12768(15) 0.14943(8) 0.24062(10) 0.0220(3) Uiso 1.000000 R
C3 C 0.71085(14) 0.15649(8) 0.25603(8) 0.0129(2) Uani 1.000000 .
H3 H 0.76186(14) 0.19436(8) 0.20242(8) 0.0155(3) Uiso 1.000000 R
C4 C 0.73480(13) 0.05967(8) 0.44909(8) 0.0136(2) Uani 1.000000 .
C5 C 0.77540(14) 0.32067(8) 0.35376(9) 0.0142(2) Uani 1.000000 .
H5 H 0.79522(14) 0.34645(8) 0.43060(9) 0.0171(3) Uiso 1.000000 R
C6 C 0.52057(14) 0.14093(7) 0.20297(9) 0.0136(2) Uani 1.000000 .
C7 C 0.73276(14) -0.01185(8) 0.54123(9) 0.0152(2) Uani 1.000000 .
H7a H 0.83411(14) -0.00216(8) 0.60297(9) 0.0183(3) Uiso 1.000000 R
H7b H 0.62615(14) -0.00476(8) 0.56862(9) 0.0183(3) Uiso 1.000000 R
C8 C 0.80930(14) -0.09464(8) 0.38135(9) 0.0161(2) Uani 1.000000 .
H8a H 0.74629(14) -0.13417(8) 0.31816(9) 0.0193(3) Uiso 1.000000 R
H8b H 0.93409(14) -0.10946(8) 0.39450(9) 0.0193(3) Uiso 1.000000 R
C9 C 0.38835(14) 0.15581(8) 0.25716(9) 0.0152(2) Uani 1.000000 .
H9 H 0.41483(14) 0.17692(8) 0.33159(9) 0.0183(3) Uiso 1.000000 R
C10 C 0.17750(15) 0.11025(8) 0.09366(10) 0.0210(3) Uani 1.000000 .
H10 H 0.06077(15) 0.09966(8) 0.05665(10) 0.0252(3) Uiso 1.000000 R
C11 C 0.93678(15) 0.34291(8) 0.31202(9) 0.0177(2) Uani 1.000000 .
H11a H 1.0348(3) 0.3065(5) 0.3563(5) 0.0265(4) Uiso 1.000000 GR
H11b H 0.9185(4) 0.3224(6) 0.2351(2) 0.0265(4) Uiso 1.000000 GR
H11c H 0.9608(6) 0.41415(12) 0.3179(7) 0.0265(4) Uiso 1.000000 GR
C12 C 0.47934(15) 0.11168(8) 0.09294(9) 0.0175(3) Uani 1.000000 .
H12 H 0.56873(15) 0.10238(8) 0.05496(9) 0.0210(3) Uiso 1.000000 R
C13 C 0.30887(16) 0.09606(9) 0.03853(10) 0.0215(3) Uani 1.000000 .
H13 H 0.28201(16) 0.07573(9) -0.03617(10) 0.0257(3) Uiso 1.000000 R
C14 C 0.61749(15) 0.37346(8) 0.28609(10) 0.0191(3) Uani 1.000000 .
H14a H 0.5925(7) 0.3483(5) 0.2106(2) 0.0287(4) Uiso 1.000000 GR
H14b H 0.5183(3) 0.3613(5) 0.3184(4) 0.0287(4) Uiso 1.000000 GR
H14c H 0.6401(4) 0.44481(11) 0.2857(6) 0.0287(4) Uiso 1.000000 GR
C15 C 0.73955(15) -0.11398(8) 0.48528(10) 0.0180(3) Uani 1.000000 .
H15a H 0.81680(15) -0.15980(8) 0.53558(10) 0.0216(3) Uiso 1.000000 R
H15b H 0.62299(15) -0.14376(8) 0.46501(10) 0.0216(3) Uiso 1.000000 R


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 C 1.2352(13) . ?
O2 C1 1.3580(13) . ?
O2 C3 1.4632(12) . ?
N2 C 1.3712(13) . ?
N2 C3 1.4541(13) . ?
N2 C5 1.4809(13) . ?
C C4 1.4606(15) . ?
C1 C4 1.3382(15) . ?
C1 C8 1.4936(15) . ?
C2 H2 0.9500 . ?
C2 C9 1.3931(16) . ?
C2 C10 1.3887(17) . ?
C3 H3 1.0000 . ?
C3 C6 1.5238(15) . ?
C4 C7 1.5062(14) . ?
C5 H5 1.0000 . ?
C5 C11 1.5234(15) . ?
C5 C14 1.5231(15) . ?
C6 C9 1.3907(16) . ?
C6 C12 1.3968(15) . ?
C7 H7a 0.9900 . ?
C7 H7b 0.9900 . ?
C7 C15 1.5526(15) . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C15 1.5478(16) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C13 1.3914(18) . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 0.9800 . ?
C12 H12 0.9500 . ?
C12 C13 1.3888(17) . ?
C13 H13 0.9500 . ?
C14 H14a 0.9800 . ?
C14 H14b 0.9800 . ?
C14 H14c 0.9800 . ?
C15 H15a 0.9900 . ?
C15 H15b 0.9900 . ?

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
C3 O2 C1 112.03(8) . . ?
C3 N2 C 120.63(9) . . ?
C5 N2 C 120.34(9) . . ?
C5 N2 C3 118.80(8) . . ?
N2 C O1 122.95(10) . . ?
C4 C O1 123.33(9) . . ?
C4 C N2 113.49(9) . . ?
C4 C1 O2 124.47(10) . . ?
C8 C1 O2 121.50(9) . . ?
C8 C1 C4 113.85(10) . . ?
C9 C2 H2 119.94(7) . . ?
C10 C2 H2 119.94(7) . . ?
C10 C2 C9 120.12(11) . . ?
N2 C3 O2 111.06(8) . . ?
H3 C3 O2 107.12(5) . . ?
H3 C3 N2 107.12(5) . . ?
C6 C3 O2 108.59(8) . . ?
C6 C3 N2 115.43(9) . . ?
C6 C3 H3 107.12(5) . . ?
C1 C4 C 119.97(10) . . ?
C7 C4 C 127.15(9) . . ?
C7 C4 C1 111.10(9) . . ?
H5 C5 N2 107.47(5) . . ?
C11 C5 N2 110.90(9) . . ?
C11 C5 H5 107.47(6) . . ?
C14 C5 N2 111.48(9) . . ?
C14 C5 H5 107.47(6) . . ?
C14 C5 C11 111.82(9) . . ?
C9 C6 C3 123.80(9) . . ?
C12 C6 C3 117.05(10) . . ?
C12 C6 C9 119.14(10) . . ?
H7a C7 C4 111.26(6) . . ?
H7b C7 C4 111.26(6) . . ?
H7b C7 H7a 109.2 . . ?
C15 C7 C4 102.52(8) . . ?
C15 C7 H7a 111.26(6) . . ?
C15 C7 H7b 111.26(6) . . ?
H8a C8 C1 111.44(6) . . ?
H8b C8 C1 111.44(6) . . ?
H8b C8 H8a 109.3 . . ?
C15 C8 C1 101.64(9) . . ?
C15 C8 H8a 111.44(6) . . ?
C15 C8 H8b 111.44(6) . . ?
C6 C9 C2 120.35(10) . . ?
H9 C9 C2 119.82(7) . . ?
H9 C9 C6 119.82(6) . . ?
H10 C10 C2 120.05(7) . . ?
C13 C10 C2 119.90(11) . . ?
C13 C10 H10 120.05(7) . . ?
H11a C11 C5 109.5 . . ?
H11b C11 C5 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C5 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
H12 C12 C6 119.69(7) . . ?
C13 C12 C6 120.61(11) . . ?
C13 C12 H12 119.69(7) . . ?
C12 C13 C10 119.86(11) . . ?
H13 C13 C10 120.07(7) . . ?
H13 C13 C12 120.07(7) . . ?
H14a C14 C5 109.5 . . ?
H14b C14 C5 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C5 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
C8 C15 C7 106.54(9) . . ?
H15a C15 C7 110.42(6) . . ?
H15a C15 C8 110.42(6) . . ?
H15b C15 C7 110.42(6) . . ?
H15b C15 C8 110.42(6) . . ?
H15b C15 H15a 108.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C N2 C3 -171.50(10) . . . . ?
O1 C N2 C5 2.98(13) . . . . ?
O1 C C4 C1 -160.32(11) . . . . ?
O1 C C4 C7 3.03(13) . . . . ?
O2 C1 C4 C -10.31(12) . . . . ?
O2 C1 C4 C7 -176.14(10) . . . . ?
O2 C1 C8 C15 -171.21(11) . . . . ?
O2 C3 N2 C -43.97(10) . . . . ?
O2 C3 N2 C5 141.47(8) . . . . ?
O2 C3 C6 C9 110.02(8) . . . . ?
O2 C3 C6 C12 -71.13(9) . . . . ?
N2 C C4 C1 14.40(11) . . . . ?
N2 C C4 C7 177.75(8) . . . . ?
N2 C3 C6 C9 -15.41(11) . . . . ?
N2 C3 C6 C12 163.44(9) . . . . ?
C C4 C1 C8 164.98(10) . . . . ?
C C4 C7 C15 -176.62(12) . . . . ?
C1 C4 C7 C15 -12.05(10) . . . . ?
C1 C8 C15 C7 -19.94(9) . . . . ?
C2 C9 C6 C3 -179.99(10) . . . . ?
C2 C9 C6 C12 1.19(12) . . . . ?
C2 C10 C13 C12 -0.03(13) . . . . ?
C3 C6 C12 C13 -179.92(10) . . . . ?
C4 C7 C15 C8 19.72(9) . . . . ?
C6 C12 C13 C10 0.43(13) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.717
####################################################################### 
# 
# 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_exp_1495_1
_database_code_depnum_ccdc_archive 'CCDC 2213241'
loop_
_audit_author_name
_audit_author_address
'Jian-Liang Ye'
;College of Chemistry and Chemical Engineering, Xiamen University
China
;
_audit_update_record             
;
2022-10-16 deposited with the CCDC.	2023-03-05 downloaded from the CCDC.
;
_audit_creation_date             2022-10-16
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H23 N O3'
_chemical_formula_sum            'C18 H23 N O3'
_chemical_formula_weight         301.37
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.7240(3)
_cell_length_b                   12.93561(17)
_cell_length_c                   17.1001(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.2436(19)
_cell_angle_gamma                90
_cell_volume                     3263.31(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4349
_cell_measurement_temperature    293
_cell_measurement_theta_max      73.9740
_cell_measurement_theta_min      4.7390
_shelx_estimated_absorpt_T_max   0.878
_shelx_estimated_absorpt_T_min   0.825
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0117
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6163
_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         73.798
_diffrn_reflns_theta_min         4.546
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_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    -31.00  -6.00   1.00    1.19    --  -42.48 125.00 -90.00   25
  2  ω   -112.00 -21.00   1.00    1.19    --  -42.48 -37.00  90.00   91
  3  ω    -69.00  15.00   1.00    1.19    --  -42.48  57.00  90.00   84
  4  ω     62.00 177.00   1.00    6.00    --  106.96  15.00   0.00  115
  5  ω     47.00 129.00   1.00    6.00    --  106.96 -45.00  90.00   82
  6  ω    101.00 127.00   1.00    6.00    --  106.96 125.00  30.00   26
  7  ω    103.00 177.00   1.00    6.00    --  106.96  77.00  30.00   74
  8  ω    145.00 175.00   1.00    6.00    --  106.96 125.00  30.00   30
  9  ω    131.00 156.00   1.00    6.00    --  106.96  77.00-150.00   25
 10  ω     29.00  89.00   1.00    6.00    --  106.96 -94.00 120.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0955761000
_diffrn_orient_matrix_UB_12      -0.0369807000
_diffrn_orient_matrix_UB_13      0.0073571000
_diffrn_orient_matrix_UB_21      -0.0190566000
_diffrn_orient_matrix_UB_22      0.0294669000
_diffrn_orient_matrix_UB_23      -0.0918155000
_diffrn_orient_matrix_UB_31      0.0375146000
_diffrn_orient_matrix_UB_32      0.1092852000
_diffrn_orient_matrix_UB_33      0.0272205000
_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                2829
_reflns_number_total             3209
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0035(2)
_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   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.062
_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)+(0.0736P)²+1.1957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1374
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C6(H6), C16(H16)
1.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B), C17(H17A,H17B), C19(H19A,H19B)
1.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
1.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.36890(7) 0.04092(7) 0.18612(7) 0.0505(3) Uani 1 1 d . . . . .
O1 O 0.25956(9) -0.22527(9) 0.22499(8) 0.0645(3) Uani 1 1 d . . . . .
N1 N 0.26061(9) -0.04954(9) 0.22845(7) 0.0502(3) Uani 1 1 d . . . . .
C2 C 0.38660(9) -0.04890(11) 0.15211(8) 0.0463(3) Uani 1 1 d . . . . .
C3 C 0.34312(10) -0.13691(11) 0.15394(9) 0.0481(3) Uani 1 1 d . . . . .
O4 O 0.01858(10) 0.14961(10) -0.12214(8) 0.0769(4) Uani 1 1 d . . . . .
C5 C 0.28323(10) -0.14239(11) 0.20401(9) 0.0488(3) Uani 1 1 d . . . . .
C6 C 0.27905(10) 0.04458(11) 0.19099(9) 0.0465(3) Uani 1 1 d . . . . .
H6 H 0.278348 0.101671 0.228439 0.056 Uiso 1 1 calc R U . . .
C7 C 0.08402(11) 0.12894(12) -0.04716(9) 0.0523(4) Uani 1 1 d . . . . .
C8 C 0.21035(9) 0.07029(10) 0.10613(8) 0.0437(3) Uani 1 1 d . . . . .
C9 C 0.20204(11) 0.17200(11) 0.08026(10) 0.0537(4) Uani 1 1 d . . . . .
H9 H 0.239313 0.221642 0.114774 0.064 Uiso 1 1 calc R U . . .
C10 C 0.13977(12) 0.20221(11) 0.00435(10) 0.0560(4) Uani 1 1 d . . . . .
H10 H 0.135515 0.271220 -0.011816 0.067 Uiso 1 1 calc R U . . .
C11 C 0.45990(11) -0.03679(13) 0.11617(11) 0.0573(4) Uani 1 1 d . . . . .
H11A H 0.510997 -0.001318 0.155967 0.069 Uiso 1 1 calc R U . . .
H11B H 0.437915 0.005266 0.066211 0.069 Uiso 1 1 calc R U . . .
C12 C 0.15421(11) -0.00254(11) 0.05302(9) 0.0523(4) Uani 1 1 d . . . . .
H12 H 0.158491 -0.071626 0.068977 0.063 Uiso 1 1 calc R U . . .
C13 C 0.09239(11) 0.02645(12) -0.02288(10) 0.0562(4) Uani 1 1 d . . . . .
H13 H 0.056027 -0.023313 -0.058039 0.067 Uiso 1 1 calc R U . . .
C14 C 0.36260(13) -0.23490(12) 0.11566(11) 0.0612(4) Uani 1 1 d . . . . .
H14A H 0.305867 -0.268915 0.084959 0.073 Uiso 1 1 calc R U . . .
H14B H 0.397607 -0.281250 0.159596 0.073 Uiso 1 1 calc R U . . .
C15 C 0.12686(11) 0.01929(15) 0.25619(11) 0.0638(4) Uani 1 1 d . . . . .
H15A H 0.140961 0.088873 0.245426 0.096 Uiso 1 1 calc R U . . .
H15B H 0.097179 0.019864 0.296709 0.096 Uiso 1 1 calc R U . . .
H15C H 0.087509 -0.011371 0.205447 0.096 Uiso 1 1 calc R U . . .
C16 C 0.21309(11) -0.04273(13) 0.28916(10) 0.0559(4) Uani 1 1 d . . . . .
H16 H 0.196709 -0.113118 0.299755 0.067 Uiso 1 1 calc R U . . .
C17 C 0.49086(14) -0.14085(17) 0.09480(15) 0.0798(6) Uani 1 1 d . . . . .
H17A H 0.522732 -0.130406 0.055956 0.096 Uiso 1 1 calc R U . . .
H17B H 0.533114 -0.171377 0.145061 0.096 Uiso 1 1 calc R U . . .
C18 C 0.27640(14) 0.0012(2) 0.37163(11) 0.0864(7) Uani 1 1 d . . . . .
H18A H 0.331022 -0.039127 0.390740 0.130 Uiso 1 1 calc R U . . .
H18B H 0.247006 -0.001352 0.412322 0.130 Uiso 1 1 calc R U . . .
H18C H 0.291004 0.071532 0.363680 0.130 Uiso 1 1 calc R U . . .
C19 C 0.41452(15) -0.21382(16) 0.05745(14) 0.0772(6) Uani 1 1 d . . . . .
H19A H 0.438051 -0.278416 0.044494 0.093 Uiso 1 1 calc R U . . .
H19B H 0.373605 -0.185006 0.005739 0.093 Uiso 1 1 calc R U . . .
C20 C -0.00618(16) 0.25339(16) -0.14363(13) 0.0820(6) Uani 1 1 d . . . . .
H20A H -0.057582 0.255548 -0.194375 0.123 Uiso 1 1 calc R U . . .
H20B H 0.043678 0.289433 -0.151393 0.123 Uiso 1 1 calc R U . . .
H20C H -0.021483 0.285811 -0.099760 0.123 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
O2 C2 1.3702(17) . ?
O2 C6 1.4446(17) . ?
O1 C5 1.2284(18) . ?
N1 C5 1.3590(19) . ?
N1 C6 1.4509(18) . ?
N1 C16 1.4768(18) . ?
C2 C3 1.334(2) . ?
C2 C11 1.490(2) . ?
C3 C5 1.477(2) . ?
C3 C14 1.506(2) . ?
O4 C7 1.3642(19) . ?
O4 C20 1.411(2) . ?
C6 H6 0.9800 . ?
C6 C8 1.516(2) . ?
C7 C10 1.381(2) . ?
C7 C13 1.382(2) . ?
C8 C9 1.380(2) . ?
C8 C12 1.392(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C17 1.518(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(2) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C19 1.515(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 C16 1.507(2) . ?
C16 H16 0.9800 . ?
C16 C18 1.527(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C19 1.486(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
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
C2 O2 C6 113.49(10) . . ?
C5 N1 C6 119.50(11) . . ?
C5 N1 C16 121.25(12) . . ?
C6 N1 C16 119.17(12) . . ?
O2 C2 C11 112.67(12) . . ?
C3 C2 O2 122.20(13) . . ?
C3 C2 C11 125.11(13) . . ?
C2 C3 C5 119.29(13) . . ?
C2 C3 C14 121.68(13) . . ?
C5 C3 C14 118.55(12) . . ?
C7 O4 C20 118.80(15) . . ?
O1 C5 N1 122.93(13) . . ?
O1 C5 C3 121.97(13) . . ?
N1 C5 C3 115.02(12) . . ?
O2 C6 N1 110.29(11) . . ?
O2 C6 H6 107.1 . . ?
O2 C6 C8 109.82(11) . . ?
N1 C6 H6 107.1 . . ?
N1 C6 C8 114.94(12) . . ?
C8 C6 H6 107.1 . . ?
O4 C7 C10 124.80(15) . . ?
O4 C7 C13 115.65(14) . . ?
C10 C7 C13 119.55(14) . . ?
C9 C8 C6 118.24(12) . . ?
C9 C8 C12 117.90(13) . . ?
C12 C8 C6 123.85(13) . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.84(14) . . ?
C10 C9 H9 119.1 . . ?
C7 C10 C9 119.41(14) . . ?
C7 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C2 C11 H11A 109.4 . . ?
C2 C11 H11B 109.4 . . ?
C2 C11 C17 111.36(14) . . ?
H11A C11 H11B 108.0 . . ?
C17 C11 H11A 109.4 . . ?
C17 C11 H11B 109.4 . . ?
C8 C12 H12 119.6 . . ?
C13 C12 C8 120.80(14) . . ?
C13 C12 H12 119.6 . . ?
C7 C13 H13 119.8 . . ?
C12 C13 C7 120.48(14) . . ?
C12 C13 H13 119.8 . . ?
C3 C14 H14A 109.3 . . ?
C3 C14 H14B 109.3 . . ?
C3 C14 C19 111.79(14) . . ?
H14A C14 H14B 107.9 . . ?
C19 C14 H14A 109.3 . . ?
C19 C14 H14B 109.3 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
N1 C16 C15 112.17(13) . . ?
N1 C16 H16 107.7 . . ?
N1 C16 C18 110.16(14) . . ?
C15 C16 H16 107.7 . . ?
C15 C16 C18 111.25(15) . . ?
C18 C16 H16 107.7 . . ?
C11 C17 H17A 109.0 . . ?
C11 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C19 C17 C11 112.82(16) . . ?
C19 C17 H17A 109.0 . . ?
C19 C17 H17B 109.0 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.3 . . ?
C14 C19 H19B 109.3 . . ?
C17 C19 C14 111.76(16) . . ?
C17 C19 H19A 109.3 . . ?
C17 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 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
O2 C2 C3 C5 -8.7(2) . . . . ?
O2 C2 C3 C14 179.44(14) . . . . ?
O2 C2 C11 C17 168.65(14) . . . . ?
O2 C6 C8 C9 -78.75(15) . . . . ?
O2 C6 C8 C12 102.07(15) . . . . ?
N1 C6 C8 C9 156.21(13) . . . . ?
N1 C6 C8 C12 -22.96(18) . . . . ?
C2 O2 C6 N1 49.26(15) . . . . ?
C2 O2 C6 C8 -78.41(14) . . . . ?
C2 C3 C5 O1 -161.64(15) . . . . ?
C2 C3 C5 N1 15.0(2) . . . . ?
C2 C3 C14 C19 -15.6(2) . . . . ?
C2 C11 C17 C19 40.2(2) . . . . ?
C3 C2 C11 C17 -9.7(2) . . . . ?
C3 C14 C19 C17 45.6(2) . . . . ?
O4 C7 C10 C9 178.13(15) . . . . ?
O4 C7 C13 C12 -177.77(15) . . . . ?
C5 N1 C6 O2 -44.46(17) . . . . ?
C5 N1 C6 C8 80.34(16) . . . . ?
C5 N1 C16 C15 -125.26(16) . . . . ?
C5 N1 C16 C18 110.23(18) . . . . ?
C5 C3 C14 C19 172.50(16) . . . . ?
C6 O2 C2 C3 -24.70(19) . . . . ?
C6 O2 C2 C11 156.85(12) . . . . ?
C6 N1 C5 O1 -170.55(15) . . . . ?
C6 N1 C5 C3 12.8(2) . . . . ?
C6 N1 C16 C15 51.40(19) . . . . ?
C6 N1 C16 C18 -73.11(19) . . . . ?
C6 C8 C9 C10 -178.77(13) . . . . ?
C6 C8 C12 C13 179.14(13) . . . . ?
C8 C9 C10 C7 0.2(2) . . . . ?
C8 C12 C13 C7 -1.0(2) . . . . ?
C9 C8 C12 C13 0.0(2) . . . . ?
C10 C7 C13 C12 1.6(2) . . . . ?
C11 C2 C3 C5 169.56(14) . . . . ?
C11 C2 C3 C14 -2.3(2) . . . . ?
C11 C17 C19 C14 -59.6(3) . . . . ?
C12 C8 C9 C10 0.5(2) . . . . ?
C13 C7 C10 C9 -1.2(2) . . . . ?
C14 C3 C5 O1 10.5(2) . . . . ?
C14 C3 C5 N1 -172.83(14) . . . . ?
C16 N1 C5 O1 6.1(2) . . . . ?
C16 N1 C5 C3 -170.55(13) . . . . ?
C16 N1 C6 O2 138.82(13) . . . . ?
C16 N1 C6 C8 -96.38(15) . . . . ?
C20 O4 C7 C10 -11.7(3) . . . . ?
C20 O4 C7 C13 167.70(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.220
_oxdiff_exptl_absorpt_empirical_full_min 0.820
####################################################################### 
# 
# 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_exp_3588
_database_code_depnum_ccdc_archive 'CCDC 2213239'
loop_
_audit_author_name
_audit_author_address
'Jian-Liang Ye'
;College of Chemistry and Chemical Engineering, Xiamen University
China
;
_audit_update_record             
;
2022-10-16 deposited with the CCDC.	2023-03-05 downloaded from the CCDC.
;
_audit_creation_date             2022-10-16
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H23 N O2'
_chemical_formula_sum            'C19 H23 N O2'
_chemical_formula_weight         297.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   15.8861(2)
_cell_length_b                   9.81570(10)
_cell_length_c                   10.53650(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.7530(10)
_cell_angle_gamma                90
_cell_volume                     1581.28(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8531
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.6970
_cell_measurement_theta_min      4.6350
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.742
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
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    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15471
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.822
_diffrn_reflns_theta_min         2.890
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     77.00 178.00   0.50    0.12    --  102.25  45.00   0.00  202
  2  ω     82.00 174.00   0.50    0.12    --  102.25  30.00 -60.00  184
  3  ω    136.00 167.00   0.50    0.12    --  102.25 125.00 120.00   62
  4  ω     85.00 116.00   0.50    0.12    --  102.25  30.00  90.00   62
  5  ω     17.00  43.00   0.50    0.05    --   43.10 -38.00   0.00   52
  6  ω    -14.00  14.00   0.50    0.05    --   43.10 -38.00   0.00   56
  7  ω    -35.00  26.00   0.50    0.05    --   43.10 -19.00 120.00  122
  8  ω     35.00  95.00   0.50    0.05    --   43.10-125.00  90.00  120
  9  ω     32.00  58.00   0.50    0.12    --  102.25-125.00  60.00   52
 10  ω     37.00  74.00   0.50    0.12    --  102.25-125.00 -30.00   74
 11  ω     78.00 117.00   0.50    0.12    --  102.25-125.00 -30.00   78
 12  ω     74.00 116.00   0.50    0.12    --  102.25-125.00  60.00   84
 13  ω     37.00 117.00   0.50    0.12    --  102.25-125.00  90.00  160
 14  ω     63.00 108.00   0.50    0.12    --  102.25 -94.00 150.00   90
 15  ω     60.00  94.00   0.50    0.12    --  102.25 -94.00 120.00   68
 16  ω     56.00 105.00   0.50    0.12    --  102.25 -77.00 150.00   98
 17  ω     30.00  71.00   0.50    0.12    --  102.25 -61.00 -90.00   82
 18  ω     44.00  69.00   0.50    0.12    --  102.25 -61.00-150.00   50
 19  ω     25.00  50.00   0.50    0.12    --  102.25 -45.00-150.00   50
 20  ω     25.00  50.00   0.50    0.12    --  102.25 -45.00   0.00   50
 21  ω    -43.00  -2.00   0.50    0.05    --  -43.10  38.00-120.00   82
 22  ω    -49.00 -22.00   0.50    0.12    --  -90.25  45.00-150.00   54
 23  ω    -69.00 -44.00   0.50    0.12    --  -90.25  61.00 -90.00   50
 24  ω    -50.00 -13.00   0.50    0.12    --  -90.25  45.00-180.00   74
 25  ω   -101.00 -53.00   0.50    0.12    --  -90.25  77.00 -30.00   96
 26  ω   -105.00 -74.00   0.50    0.12    --  -90.25  77.00  60.00   62
 27  ω    -52.00 -25.00   0.50    0.12    --  -90.25  77.00  60.00   54
 28  ω    -90.00 -19.00   0.50    0.12    --  -90.25 125.00  60.00  142
 29  ω   -169.00 -65.00   0.50    0.12    --  -90.25 -30.00  90.00  208
 30  ω   -167.00-134.00   0.50    0.12    --  -90.25 -45.00-180.00   66
 31  ω   -132.00 -70.00   0.50    0.12    --  -90.25 -45.00-180.00  124
 32  ω   -117.00 -12.00   0.50    0.05    --  -43.10 -77.00 -90.00  210
 33  ω   -108.00 -73.00   0.50    0.05    --  -43.10-125.00-180.00   70
 34  ω   -118.00 -71.00   0.50    0.05    --  -43.10-125.00 -60.00   94
 35  ω   -159.00-102.00   0.50    0.12    --  -90.25-125.00 -30.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0769432000
_diffrn_orient_matrix_UB_12      0.1008907000
_diffrn_orient_matrix_UB_13      0.0407203000
_diffrn_orient_matrix_UB_21      0.0649230000
_diffrn_orient_matrix_UB_22      -0.1200572000
_diffrn_orient_matrix_UB_23      0.0258116000
_diffrn_orient_matrix_UB_31      0.0045108000
_diffrn_orient_matrix_UB_32      0.0069822000
_diffrn_orient_matrix_UB_33      -0.1440268000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2821
_reflns_number_total             3038
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0077(5)
_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   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.034
_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+0.8518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1112
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C006(H006), C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00C,H00D), C00D(H00E,H00F), C00G(H00I,H00J), C00H(H00K,H00L), C00J(H00N,
 H00O), C00K(H00P,H00Q), C00L(H00R,H00S), C00M(H00T,H00U)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00E(H00G), C00F(H00H), C00I(H00M)
;
_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
O001 O 0.83273(6) 0.72239(9) 0.80534(8) 0.0215(2) Uani 1 1 d . . . . .
O002 O 0.72129(6) 0.96643(9) 0.49210(9) 0.0227(2) Uani 1 1 d . . . . .
N003 N 0.70838(7) 0.79047(11) 0.62832(10) 0.0183(3) Uani 1 1 d . . . . .
C004 C 0.76504(8) 0.55142(13) 0.64303(12) 0.0185(3) Uani 1 1 d . . . . .
C005 C 0.75597(8) 0.87986(13) 0.57533(12) 0.0185(3) Uani 1 1 d . . . . .
C006 C 0.61333(8) 0.81021(13) 0.60503(12) 0.0192(3) Uani 1 1 d . . . . .
H006 H 0.593662 0.874301 0.528941 0.023 Uiso 1 1 calc R U . . .
C007 C 0.84997(8) 0.87096(13) 0.63506(13) 0.0211(3) Uani 1 1 d . . . . .
C008 C 0.75025(8) 0.67962(13) 0.71444(12) 0.0187(3) Uani 1 1 d . . . . .
H008 H 0.710207 0.654441 0.769333 0.022 Uiso 1 1 calc R U . . .
C009 C 0.88082(9) 0.80327(13) 0.74784(13) 0.0219(3) Uani 1 1 d . . . . .
C00A C 0.78760(9) 0.55359(14) 0.52415(13) 0.0230(3) Uani 1 1 d . . . . .
H00A H 0.793675 0.638157 0.483683 0.028 Uiso 1 1 calc R U . . .
C00B C 0.75465(8) 0.42634(14) 0.69971(13) 0.0222(3) Uani 1 1 d . . . . .
H00B H 0.739098 0.423812 0.780601 0.027 Uiso 1 1 calc R U . . .
C00C C 0.59326(9) 0.87709(14) 0.72397(14) 0.0247(3) Uani 1 1 d . . . . .
H00C H 0.624007 0.965676 0.741801 0.030 Uiso 1 1 calc R U . . .
H00D H 0.615136 0.818421 0.802439 0.030 Uiso 1 1 calc R U . . .
C00D C 0.49476(9) 0.89989(14) 0.70034(14) 0.0246(3) Uani 1 1 d . . . . .
H00E H 0.483417 0.936359 0.781744 0.030 Uiso 1 1 calc R U . . .
H00F H 0.474520 0.968378 0.629649 0.030 Uiso 1 1 calc R U . . .
C00E C 0.79063(9) 0.30819(15) 0.52114(14) 0.0274(3) Uani 1 1 d . . . . .
H00G H 0.799538 0.225529 0.479701 0.033 Uiso 1 1 calc R U . . .
C00F C 0.76694(9) 0.30523(14) 0.63850(14) 0.0268(3) Uani 1 1 d . . . . .
H00H H 0.759096 0.220377 0.677139 0.032 Uiso 1 1 calc R U . . .
C00G C 0.44332(9) 0.76882(15) 0.66125(14) 0.0243(3) Uani 1 1 d . . . . .
H00I H 0.379938 0.788667 0.640488 0.029 Uiso 1 1 calc R U . . .
H00J H 0.458136 0.704120 0.736108 0.029 Uiso 1 1 calc R U . . .
C00H C 0.56199(9) 0.67824(14) 0.56768(13) 0.0223(3) Uani 1 1 d . . . . .
H00K H 0.581214 0.611263 0.640028 0.027 Uiso 1 1 calc R U . . .
H00L H 0.573944 0.639432 0.487601 0.027 Uiso 1 1 calc R U . . .
C00I C 0.80123(10) 0.43220(15) 0.46462(14) 0.0267(3) Uani 1 1 d . . . . .
H00M H 0.817933 0.434323 0.384641 0.032 Uiso 1 1 calc R U . . .
C00J C 0.46388(9) 0.70410(15) 0.54180(14) 0.0258(3) Uani 1 1 d . . . . .
H00N H 0.443790 0.765107 0.464666 0.031 Uiso 1 1 calc R U . . .
H00O H 0.431900 0.616802 0.520921 0.031 Uiso 1 1 calc R U . . .
C00K C 0.92053(9) 0.95574(15) 0.60347(16) 0.0304(3) Uani 1 1 d . . . . .
H00P H 0.910396 1.054134 0.613806 0.037 Uiso 1 1 calc R U . . .
H00Q H 0.924193 0.938417 0.512556 0.037 Uiso 1 1 calc R U . . .
C00L C 0.97464(9) 0.83209(16) 0.81455(16) 0.0319(4) Uani 1 1 d . . . . .
H00R H 1.008287 0.746956 0.840746 0.038 Uiso 1 1 calc R U . . .
H00S H 0.981003 0.890486 0.893201 0.038 Uiso 1 1 calc R U . . .
C00M C 1.00322(11) 0.9068(2) 0.7057(2) 0.0559(6) Uani 1 1 d . . . . .
H00T H 1.036970 0.844757 0.664001 0.067 Uiso 1 1 calc R U . . .
H00U H 1.040771 0.985491 0.743201 0.067 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
O001 C008 1.4591(15) . ?
O001 C009 1.3536(17) . ?
O002 C005 1.2379(16) . ?
N003 C005 1.3720(17) . ?
N003 C006 1.4754(16) . ?
N003 C008 1.4567(16) . ?
C004 C008 1.5169(18) . ?
C004 C00A 1.3934(19) . ?
C004 C00B 1.3945(18) . ?
C005 C007 1.4571(18) . ?
C006 H006 1.0000 . ?
C006 C00C 1.5232(18) . ?
C006 C00H 1.5244(18) . ?
C007 C009 1.3332(19) . ?
C007 C00K 1.5041(19) . ?
C008 H008 1.0000 . ?
C009 C00L 1.4922(19) . ?
C00A H00A 0.9500 . ?
C00A C00I 1.3906(19) . ?
C00B H00B 0.9500 . ?
C00B C00F 1.391(2) . ?
C00C H00C 0.9900 . ?
C00C H00D 0.9900 . ?
C00C C00D 1.5327(18) . ?
C00D H00E 0.9900 . ?
C00D H00F 0.9900 . ?
C00D C00G 1.520(2) . ?
C00E H00G 0.9500 . ?
C00E C00F 1.387(2) . ?
C00E C00I 1.385(2) . ?
C00F H00H 0.9500 . ?
C00G H00I 0.9900 . ?
C00G H00J 0.9900 . ?
C00G C00J 1.5222(19) . ?
C00H H00K 0.9900 . ?
C00H H00L 0.9900 . ?
C00H C00J 1.5289(19) . ?
C00I H00M 0.9500 . ?
C00J H00N 0.9900 . ?
C00J H00O 0.9900 . ?
C00K H00P 0.9900 . ?
C00K H00Q 0.9900 . ?
C00K C00M 1.533(2) . ?
C00L H00R 0.9900 . ?
C00L H00S 0.9900 . ?
C00L C00M 1.530(3) . ?
C00M H00T 0.9900 . ?
C00M H00U 0.9900 . ?

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
C009 O001 C008 112.97(10) . . ?
C005 N003 C006 120.03(10) . . ?
C005 N003 C008 121.48(11) . . ?
C008 N003 C006 118.38(10) . . ?
C00A C004 C008 123.06(12) . . ?
C00A C004 C00B 119.18(12) . . ?
C00B C004 C008 117.76(12) . . ?
O002 C005 N003 122.60(12) . . ?
O002 C005 C007 123.64(12) . . ?
N003 C005 C007 113.53(11) . . ?
N003 C006 H006 107.4 . . ?
N003 C006 C00C 110.68(10) . . ?
N003 C006 C00H 112.52(11) . . ?
C00C C006 H006 107.4 . . ?
C00C C006 C00H 111.21(11) . . ?
C00H C006 H006 107.4 . . ?
C005 C007 C00K 127.53(12) . . ?
C009 C007 C005 120.03(12) . . ?
C009 C007 C00K 110.94(12) . . ?
O001 C008 C004 109.38(10) . . ?
O001 C008 H008 106.9 . . ?
N003 C008 O001 111.77(10) . . ?
N003 C008 C004 114.63(10) . . ?
N003 C008 H008 106.9 . . ?
C004 C008 H008 106.9 . . ?
O001 C009 C00L 120.88(12) . . ?
C007 C009 O001 125.15(12) . . ?
C007 C009 C00L 113.81(13) . . ?
C004 C00A H00A 119.9 . . ?
C00I C00A C004 120.12(13) . . ?
C00I C00A H00A 119.9 . . ?
C004 C00B H00B 119.8 . . ?
C00F C00B C004 120.40(13) . . ?
C00F C00B H00B 119.8 . . ?
C006 C00C H00C 109.4 . . ?
C006 C00C H00D 109.4 . . ?
C006 C00C C00D 111.21(11) . . ?
H00C C00C H00D 108.0 . . ?
C00D C00C H00C 109.4 . . ?
C00D C00C H00D 109.4 . . ?
C00C C00D H00E 109.3 . . ?
C00C C00D H00F 109.3 . . ?
H00E C00D H00F 107.9 . . ?
C00G C00D C00C 111.75(11) . . ?
C00G C00D H00E 109.3 . . ?
C00G C00D H00F 109.3 . . ?
C00F C00E H00G 120.1 . . ?
C00I C00E H00G 120.1 . . ?
C00I C00E C00F 119.71(13) . . ?
C00B C00F H00H 120.0 . . ?
C00E C00F C00B 120.10(13) . . ?
C00E C00F H00H 120.0 . . ?
C00D C00G H00I 109.5 . . ?
C00D C00G H00J 109.5 . . ?
C00D C00G C00J 110.92(11) . . ?
H00I C00G H00J 108.0 . . ?
C00J C00G H00I 109.5 . . ?
C00J C00G H00J 109.5 . . ?
C006 C00H H00K 109.5 . . ?
C006 C00H H00L 109.5 . . ?
C006 C00H C00J 110.67(11) . . ?
H00K C00H H00L 108.1 . . ?
C00J C00H H00K 109.5 . . ?
C00J C00H H00L 109.5 . . ?
C00A C00I H00M 119.8 . . ?
C00E C00I C00A 120.47(13) . . ?
C00E C00I H00M 119.8 . . ?
C00G C00J C00H 111.04(11) . . ?
C00G C00J H00N 109.4 . . ?
C00G C00J H00O 109.4 . . ?
C00H C00J H00N 109.4 . . ?
C00H C00J H00O 109.4 . . ?
H00N C00J H00O 108.0 . . ?
C007 C00K H00P 111.2 . . ?
C007 C00K H00Q 111.2 . . ?
C007 C00K C00M 102.65(13) . . ?
H00P C00K H00Q 109.2 . . ?
C00M C00K H00P 111.2 . . ?
C00M C00K H00Q 111.2 . . ?
C009 C00L H00R 111.5 . . ?
C009 C00L H00S 111.5 . . ?
C009 C00L C00M 101.51(12) . . ?
H00R C00L H00S 109.3 . . ?
C00M C00L H00R 111.5 . . ?
C00M C00L H00S 111.5 . . ?
C00K C00M H00T 110.2 . . ?
C00K C00M H00U 110.2 . . ?
C00L C00M C00K 107.76(14) . . ?
C00L C00M H00T 110.2 . . ?
C00L C00M H00U 110.2 . . ?
H00T C00M H00U 108.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C009 C00L C00M 171.83(14) . . . . ?
O002 C005 C007 C009 160.99(13) . . . . ?
O002 C005 C007 C00K -3.7(2) . . . . ?
N003 C005 C007 C009 -13.64(18) . . . . ?
N003 C005 C007 C00K -178.30(13) . . . . ?
N003 C006 C00C C00D 179.26(11) . . . . ?
N003 C006 C00H C00J -178.85(10) . . . . ?
C004 C00A C00I C00E 1.5(2) . . . . ?
C004 C00B C00F C00E 0.7(2) . . . . ?
C005 N003 C006 C00C -100.24(13) . . . . ?
C005 N003 C006 C00H 134.65(12) . . . . ?
C005 N003 C008 O001 40.03(16) . . . . ?
C005 N003 C008 C004 -85.14(14) . . . . ?
C005 C007 C009 O001 10.4(2) . . . . ?
C005 C007 C009 C00L -165.10(12) . . . . ?
C005 C007 C00K C00M 175.38(15) . . . . ?
C006 N003 C005 O002 -10.84(18) . . . . ?
C006 N003 C005 C007 163.86(11) . . . . ?
C006 N003 C008 O001 -136.36(11) . . . . ?
C006 N003 C008 C004 98.47(13) . . . . ?
C006 C00C C00D C00G 54.35(16) . . . . ?
C006 C00H C00J C00G -57.05(15) . . . . ?
C007 C009 C00L C00M -12.47(18) . . . . ?
C007 C00K C00M C00L -17.0(2) . . . . ?
C008 O001 C009 C007 18.56(18) . . . . ?
C008 O001 C009 C00L -166.25(12) . . . . ?
C008 N003 C005 O002 172.83(12) . . . . ?
C008 N003 C005 C007 -12.47(16) . . . . ?
C008 N003 C006 C00C 76.20(14) . . . . ?
C008 N003 C006 C00H -48.91(15) . . . . ?
C008 C004 C00A C00I 179.24(12) . . . . ?
C008 C004 C00B C00F 179.70(12) . . . . ?
C009 O001 C008 N003 -41.14(14) . . . . ?
C009 O001 C008 C004 86.89(12) . . . . ?
C009 C007 C00K C00M 9.58(18) . . . . ?
C009 C00L C00M C00K 17.8(2) . . . . ?
C00A C004 C008 O001 -90.02(14) . . . . ?
C00A C004 C008 N003 36.39(17) . . . . ?
C00A C004 C00B C00F 0.20(19) . . . . ?
C00B C004 C008 O001 90.49(13) . . . . ?
C00B C004 C008 N003 -143.09(12) . . . . ?
C00B C004 C00A C00I -1.3(2) . . . . ?
C00C C006 C00H C00J 56.34(14) . . . . ?
C00C C00D C00G C00J -54.99(16) . . . . ?
C00D C00G C00J C00H 56.35(16) . . . . ?
C00F C00E C00I C00A -0.5(2) . . . . ?
C00H C006 C00C C00D -54.89(15) . . . . ?
C00I C00E C00F C00B -0.6(2) . . . . ?
C00K C007 C009 O001 177.40(12) . . . . ?
C00K C007 C009 C00L 1.91(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.761
_oxdiff_exptl_absorpt_empirical_full_min 0.523
####################################################################### 
# 
# 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_exp_1468_1
_database_code_depnum_ccdc_archive 'CCDC 2213240'
loop_
_audit_author_name
_audit_author_address
'Jian-Liang Ye'
;College of Chemistry and Chemical Engineering, Xiamen University
China
;
_audit_update_record             
;
2022-10-16 deposited with the CCDC.	2023-03-05 downloaded from the CCDC.
;
_audit_creation_date             2022-10-16
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C17 H21 N O2'
_chemical_formula_sum            'C17 H21 N O2'
_chemical_formula_weight         271.362
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   9.91528(16)
_cell_length_b                   10.40381(18)
_cell_length_c                   28.3425(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2923.71(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3356
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2070
_cell_measurement_theta_min      5.4390
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             1171.710
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.9977
_diffrn_reflns_Laue_measured_fraction_max 0.9704
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            7062
_diffrn_reflns_point_group_measured_fraction_full 0.9977
_diffrn_reflns_point_group_measured_fraction_max 0.9704
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         73.35
_diffrn_reflns_theta_min         5.45
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.9704
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 -28.00   1.00    1.57    --  -42.23 125.00  30.00   46
  2  ω    -57.00  31.00   1.00    1.57    --  -42.23  37.00 120.00   88
  3  ω     28.00  73.00   1.00    1.57    --   42.23-125.00   0.00   45
  4  ω     87.00 137.00   1.00    6.27    --  105.38 -77.00   0.00   50
  5  ω    103.00 174.00   1.00    6.27    --  105.38  77.00 120.00   71
  6  ω     19.00 150.00   1.00    6.27    --  105.38   0.00 -30.00  131
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0350286000
_diffrn_orient_matrix_UB_12      0.0710615000
_diffrn_orient_matrix_UB_13      -0.0461077000
_diffrn_orient_matrix_UB_21      0.1405939000
_diffrn_orient_matrix_UB_22      -0.0629775000
_diffrn_orient_matrix_UB_23      -0.0000397000
_diffrn_orient_matrix_UB_31      -0.0560811000
_diffrn_orient_matrix_UB_32      -0.1136443000
_diffrn_orient_matrix_UB_33      -0.0287791000
_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         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              34
_reflns_limit_l_min              0
_reflns_number_gt                2364
_reflns_number_total             2852
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_refine_diff_density_max         0.2628
_refine_diff_density_min         -0.2515
_refine_diff_density_rms         0.0469
_refine_ls_d_res_high            0.8046
_refine_ls_d_res_low             8.1241
_refine_ls_extinction_coef       0.00030(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0363
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2852
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.0363
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.8432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.1014
_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:
 C10(H10), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C13(H13a,H13b), C15(H15a,H15b), C16(H16a,H16b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C9(H9), C11(H11)
2.d Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c)
;
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_refinement_flags_posn
O1 O -0.21477(9) -0.28445(9) -0.35825(3) 0.0210(2) Uani 1.000000 .
O0aa O -0.47110(9) -0.55592(9) -0.40397(3) 0.0241(2) Uani 1.000000 .
N1 N -0.28849(10) -0.42914(11) -0.41855(4) 0.0196(2) Uani 1.000000 .
C2 C -0.05108(13) -0.43526(12) -0.38836(4) 0.0192(3) Uani 1.000000 .
C3 C -0.36784(12) -0.45185(12) -0.33895(4) 0.0189(3) Uani 1.000000 .
C4 C 0.06183(14) -0.63492(14) -0.37098(5) 0.0265(3) Uani 1.000000 .
H4 H 0.05806(14) -0.72517(14) -0.36605(5) 0.0318(4) Uiso 1.000000 R
C5 C 0.18385(14) -0.57139(14) -0.36740(5) 0.0254(3) Uani 1.000000 .
H5 H 0.26383(14) -0.61767(14) -0.36019(5) 0.0305(4) Uiso 1.000000 R
C6 C -0.29470(12) -0.34902(12) -0.32689(4) 0.0196(3) Uani 1.000000 .
C7 C -0.37956(13) -0.48668(12) -0.38926(4) 0.0191(3) Uani 1.000000 .
C8 C 0.07146(14) -0.37146(13) -0.38468(5) 0.0233(3) Uani 1.000000 .
H8 H 0.07508(14) -0.28105(13) -0.38919(5) 0.0280(3) Uiso 1.000000 R
C9 C -0.05523(14) -0.56786(13) -0.38170(5) 0.0234(3) Uani 1.000000 .
H9 H -0.13841(14) -0.61251(13) -0.38452(5) 0.0281(4) Uiso 1.000000 R
C10 C -0.17594(13) -0.35634(12) -0.39970(4) 0.0194(3) Uani 1.000000 .
H10 H -0.14940(13) -0.29233(12) -0.42433(4) 0.0233(3) Uiso 1.000000 R
C11 C 0.18859(14) -0.43878(14) -0.37448(5) 0.0268(3) Uani 1.000000 .
H11 H 0.27217(14) -0.39453(14) -0.37231(5) 0.0321(4) Uiso 1.000000 R
C12 C -0.45850(14) -0.51934(13) -0.30416(5) 0.0238(3) Uani 1.000000 .
H12a H -0.55375(14) -0.50010(13) -0.31188(5) 0.0286(3) Uiso 1.000000 R
H12b H -0.44535(14) -0.61337(13) -0.30692(5) 0.0286(3) Uiso 1.000000 R
C13 C -0.29664(13) -0.28536(14) -0.27962(5) 0.0256(3) Uani 1.000000 .
H13a H -0.21182(13) -0.30492(14) -0.26265(5) 0.0308(4) Uiso 1.000000 R
H13b H -0.30235(13) -0.19103(14) -0.28377(5) 0.0308(4) Uiso 1.000000 R
C14 C -0.30961(15) -0.43579(14) -0.47033(4) 0.0259(3) Uani 1.000000 .
H14 H -0.36191(15) -0.51593(14) -0.47703(4) 0.0311(4) Uiso 1.000000 R
C15 C -0.42958(16) -0.47773(14) -0.25350(5) 0.0292(3) Uani 1.000000 .
H15a H -0.50370(16) -0.50683(14) -0.23267(5) 0.0350(4) Uiso 1.000000 R
H15b H -0.34496(16) -0.51835(14) -0.24249(5) 0.0350(4) Uiso 1.000000 R
C16 C -0.41640(15) -0.33174(14) -0.25049(5) 0.0279(3) Uani 1.000000 .
H16a H -0.40405(15) -0.30586(14) -0.21716(5) 0.0335(4) Uiso 1.000000 R
H16b H -0.50010(15) -0.29107(14) -0.26232(5) 0.0335(4) Uiso 1.000000 R
C17 C -0.17747(18) -0.44499(18) -0.49718(5) 0.0389(4) Uani 1.000000 .
H17a H -0.1229(6) -0.5150(8) -0.4841(3) 0.0583(6) Uiso 1.000000 GR
H17b H -0.19601(19) -0.4622(12) -0.53056(10) 0.0583(6) Uiso 1.000000 GR
H17c H -0.1282(6) -0.3638(5) -0.4942(4) 0.0583(6) Uiso 1.000000 GR
C18 C -0.3946(2) -0.32304(19) -0.48644(6) 0.0480(5) Uani 1.000000 .
H18a H -0.3450(6) -0.2429(2) -0.4811(5) 0.0720(7) Uiso 1.000000 GR
H18b H -0.4148(13) -0.3320(8) -0.52012(13) 0.0720(7) Uiso 1.000000 GR
H18c H -0.4790(7) -0.3213(8) -0.4685(4) 0.0720(7) Uiso 1.000000 GR


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 C6 1.3672(15) . ?
O1 C10 1.4450(15) . ?
O0aa C7 1.2315(16) . ?
N1 C7 1.3650(16) . ?
N1 C10 1.4507(16) . ?
N1 C14 1.4840(16) . ?
C2 C8 1.3884(18) . ?
C2 C9 1.3929(19) . ?
C2 C10 1.5200(17) . ?
C3 C6 1.3370(18) . ?
C3 C7 1.4758(17) . ?
C3 C12 1.5078(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(2) . ?
C4 C9 1.3879(19) . ?
C5 H5 0.9500 . ?
C5 C11 1.395(2) . ?
C6 C13 1.4946(18) . ?
C8 H8 0.9500 . ?
C8 C11 1.387(2) . ?
C9 H9 0.9500 . ?
C10 H10 1.0000 . ?
C11 H11 0.9500 . ?
C12 H12a 0.9900 . ?
C12 H12b 0.9900 . ?
C12 C15 1.5268(19) . ?
C13 H13a 0.9900 . ?
C13 H13b 0.9900 . ?
C13 C16 1.5245(19) . ?
C14 H14 1.0000 . ?
C14 C17 1.518(2) . ?
C14 C18 1.515(2) . ?
C15 H15a 0.9900 . ?
C15 H15b 0.9900 . ?
C15 C16 1.527(2) . ?
C16 H16a 0.9900 . ?
C16 H16b 0.9900 . ?
C17 H17a 0.9800 . ?
C17 H17b 0.9800 . ?
C17 H17c 0.9800 . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 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
C10 O1 C6 115.39(10) . . ?
C10 N1 C7 120.92(10) . . ?
C14 N1 C7 119.19(11) . . ?
C14 N1 C10 119.81(10) . . ?
C9 C2 C8 119.28(12) . . ?
C10 C2 C8 118.06(11) . . ?
C10 C2 C9 122.66(12) . . ?
C7 C3 C6 119.10(11) . . ?
C12 C3 C6 121.92(12) . . ?
C12 C3 C7 118.08(11) . . ?
C5 C4 H4 119.75(8) . . ?
C9 C4 H4 119.75(8) . . ?
C9 C4 C5 120.50(13) . . ?
H5 C5 C4 120.27(8) . . ?
C11 C5 C4 119.46(13) . . ?
C11 C5 H5 120.27(8) . . ?
C3 C6 O1 122.77(11) . . ?
C13 C6 O1 111.87(11) . . ?
C13 C6 C3 125.23(12) . . ?
N1 C7 O0aa 122.57(11) . . ?
C3 C7 O0aa 121.91(12) . . ?
C3 C7 N1 115.34(11) . . ?
H8 C8 C2 119.76(8) . . ?
C11 C8 C2 120.47(13) . . ?
C11 C8 H8 119.76(8) . . ?
C4 C9 C2 120.19(13) . . ?
H9 C9 C2 119.91(8) . . ?
H9 C9 C4 119.91(8) . . ?
N1 C10 O1 111.39(10) . . ?
C2 C10 O1 108.95(10) . . ?
C2 C10 N1 114.99(10) . . ?
H10 C10 O1 107.04(6) . . ?
H10 C10 N1 107.04(6) . . ?
H10 C10 C2 107.04(7) . . ?
C8 C11 C5 120.08(13) . . ?
H11 C11 C5 119.96(8) . . ?
H11 C11 C8 119.96(8) . . ?
H12a C12 C3 109.26(7) . . ?
H12b C12 C3 109.26(7) . . ?
H12b C12 H12a 107.9 . . ?
C15 C12 C3 111.78(11) . . ?
C15 C12 H12a 109.26(8) . . ?
C15 C12 H12b 109.26(8) . . ?
H13a C13 C6 109.48(7) . . ?
H13b C13 C6 109.48(7) . . ?
H13b C13 H13a 108.1 . . ?
C16 C13 C6 110.80(11) . . ?
C16 C13 H13a 109.48(8) . . ?
C16 C13 H13b 109.48(8) . . ?
H14 C14 N1 107.45(7) . . ?
C17 C14 N1 112.14(12) . . ?
C17 C14 H14 107.45(9) . . ?
C18 C14 N1 109.90(12) . . ?
C18 C14 H14 107.45(10) . . ?
C18 C14 C17 112.20(14) . . ?
H15a C15 C12 109.54(8) . . ?
H15b C15 C12 109.54(8) . . ?
H15b C15 H15a 108.1 . . ?
C16 C15 C12 110.53(12) . . ?
C16 C15 H15a 109.54(8) . . ?
C16 C15 H15b 109.54(8) . . ?
C15 C16 C13 110.57(12) . . ?
H16a C16 C13 109.54(7) . . ?
H16a C16 C15 109.54(7) . . ?
H16b C16 C13 109.54(8) . . ?
H16b C16 C15 109.54(8) . . ?
H16b C16 H16a 108.1 . . ?
H17a C17 C14 109.5 . . ?
H17b C17 C14 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 C14 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
H18a C18 C14 109.5 . . ?
H18b C18 C14 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C14 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 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 C6 C3 C7 -9.28(14) . . . . ?
O1 C6 C3 C12 -178.17(11) . . . . ?
O1 C6 C13 C16 162.35(11) . . . . ?
O1 C10 N1 C7 -37.79(12) . . . . ?
O1 C10 N1 C14 138.95(10) . . . . ?
O1 C10 C2 C8 -74.15(11) . . . . ?
O1 C10 C2 C9 106.00(11) . . . . ?
O0aa C7 N1 C10 -175.21(12) . . . . ?
O0aa C7 N1 C14 8.03(15) . . . . ?
O0aa C7 C3 C6 -160.09(12) . . . . ?
O0aa C7 C3 C12 9.23(15) . . . . ?
N1 C7 C3 C6 15.13(13) . . . . ?
N1 C7 C3 C12 -175.55(11) . . . . ?
N1 C10 C2 C8 160.02(11) . . . . ?
N1 C10 C2 C9 -19.83(13) . . . . ?
C2 C8 C11 C5 -0.57(15) . . . . ?
C2 C9 C4 C5 -0.87(16) . . . . ?
C3 C6 C13 C16 -13.61(14) . . . . ?
C3 C12 C15 C16 45.65(12) . . . . ?
C4 C5 C11 C8 0.45(16) . . . . ?
C6 C13 C16 C15 45.40(12) . . . . ?
C12 C15 C16 C13 -63.12(13) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.192
_oxdiff_exptl_absorpt_empirical_full_min 0.854
