# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_chenyuting-zhfm_0618_auto
_database_code_depnum_ccdc_archive 'CCDC 2470262'
loop_
_audit_author_name
_audit_author_address
'yuting chen'
;Lanzhou university
China
;
_audit_update_record             
;
2025-07-06 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;
_audit_creation_date             2025-06-18
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 N O3'
_chemical_formula_sum            'C17 H19 N O3'
_chemical_formula_weight         285.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   11.1025(2)
_cell_length_b                   7.40740(10)
_cell_length_c                   19.1639(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.410(2)
_cell_angle_gamma                90
_cell_volume                     1511.85(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5523
_cell_measurement_temperature    300.96(10)
_cell_measurement_theta_max      75.3680
_cell_measurement_theta_min      4.1380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9096
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.736
_diffrn_reflns_theta_min         4.151
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.96(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 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00 -28.00   0.50    0.05    -- -100.00  61.00 -30.00   50
  2  ω    -74.00 -35.00   0.50    0.05    -- -100.00  61.00 -60.00   78
  3  ω    -74.00 -45.00   0.50    0.05    -- -100.00  61.00 -90.00   58
  4  ω    -73.00 -36.00   0.50    0.05    -- -100.00  61.00-120.00   74
  5  ω    -54.00 -25.00   0.50    0.05    -- -100.00  45.00-150.00   58
  6  ω    -54.00 -29.00   0.50    0.05    -- -100.00  45.00 -90.00   50
  7  ω    -52.00 -27.00   0.50    0.05    -- -100.00  45.00 -30.00   50
  8  ω    -33.00  24.00   0.50    0.05    --   44.66 -19.00-150.00  114
  9  ω     -5.00  21.00   0.50    0.05    --   44.66 -19.00-180.00   52
 10  ω    -33.00  -8.00   0.50    0.05    --  -44.66  41.00 136.00   50
 11  ω    -14.00  35.00   0.50    0.05    --   44.66 -41.00 -16.00   98
 12  ω     43.00  83.00   0.50    0.05    --  108.90 -94.00  60.00   80
 13  ω     47.00 106.00   0.50    0.05    --  108.90 -94.00 -30.00  118
 14  ω     37.00  65.00   0.50    0.05    --  108.90 -61.00   0.00   56
 15  ω     38.00  63.00   0.50    0.05    --  108.90 -61.00 -30.00   50
 16  ω     38.00  65.00   0.50    0.05    --  108.90 -61.00  30.00   54
 17  ω     38.00  68.00   0.50    0.05    --  108.90 -61.00  60.00   60
 18  ω     50.00 102.00   0.50    0.05    --  108.90 -77.00 120.00  104
 19  ω     26.00 113.00   0.50    0.05    --   44.66  41.00 136.00  174
 20  ω     91.00 151.00   0.50    0.05    --  108.90  41.00 136.00  120
 21  ω    117.00 172.00   0.50    0.05    --  108.90  45.00-120.00  110
 22  ω   -119.00 -25.00   0.50    0.05    --  -44.66 -41.00 -16.00  188
 23  ω   -137.00 -80.00   0.50    0.05    -- -100.00 -41.00 -16.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0773045000
_diffrn_orient_matrix_UB_12      -0.0532282000
_diffrn_orient_matrix_UB_13      0.0774202000
_diffrn_orient_matrix_UB_21      0.0973314000
_diffrn_orient_matrix_UB_22      -0.0932984000
_diffrn_orient_matrix_UB_23      -0.0313719000
_diffrn_orient_matrix_UB_31      0.0740633000
_diffrn_orient_matrix_UB_32      0.1780317000
_diffrn_orient_matrix_UB_33      0.0066726000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2533
_reflns_number_total             2976
_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 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.086
_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)+(0.0628P)²+0.2159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1216
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C11(H11A,H11B), C14(H14A,H14B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C9(H9), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_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 0.50232(9) 0.07430(14) 0.41143(5) 0.0486(3) Uani 1 1 d . . . . .
O2 O 0.73250(10) 0.3783(2) 0.32314(6) 0.0693(4) Uani 1 1 d . . . . .
O3 O 0.52683(9) 0.34949(15) 0.30850(5) 0.0492(3) Uani 1 1 d . . . . .
N1 N 0.61567(10) 0.18376(15) 0.52268(5) 0.0378(3) Uani 1 1 d . . . . .
H1 H 0.581792 0.118879 0.549229 0.045 Uiso 1 1 calc R U . . .
C1 C 0.58148(12) 0.17616(17) 0.44990(7) 0.0358(3) Uani 1 1 d . . . . .
C2 C 0.36175(17) 0.3650(3) 0.19947(9) 0.0689(5) Uani 1 1 d . . . . .
H2A H 0.340626 0.368744 0.147340 0.103 Uiso 1 1 calc R U . . .
H2B H 0.326642 0.468332 0.216812 0.103 Uiso 1 1 calc R U . . .
H2C H 0.328341 0.256822 0.214421 0.103 Uiso 1 1 calc R U . . .
C3 C 0.76000(17) 0.6284(2) 0.60541(10) 0.0619(4) Uani 1 1 d . . . . .
H3A H 0.729012 0.721925 0.631308 0.074 Uiso 1 1 calc R U . . .
H3B H 0.842990 0.593368 0.634837 0.074 Uiso 1 1 calc R U . . .
C4 C 0.71622(11) 0.31322(17) 0.55242(7) 0.0359(3) Uani 1 1 d . . . . .
C5 C 0.50077(15) 0.3666(2) 0.23026(7) 0.0527(4) Uani 1 1 d . . . . .
H5A H 0.537928 0.266897 0.210847 0.063 Uiso 1 1 calc R U . . .
H5B H 0.535304 0.478603 0.218026 0.063 Uiso 1 1 calc R U . . .
C6 C 0.73486(11) 0.39419(17) 0.48358(7) 0.0367(3) Uani 1 1 d . . . . .
C7 C 0.92787(17) 0.0352(3) 0.70573(9) 0.0673(5) Uani 1 1 d . . . . .
H7 H 0.926016 -0.009467 0.750766 0.081 Uiso 1 1 calc R U . . .
C8 C 0.65823(12) 0.31388(17) 0.42532(7) 0.0361(3) Uani 1 1 d . . . . .
C9 C 0.83111(15) 0.1420(2) 0.66606(8) 0.0519(4) Uani 1 1 d . . . . .
H9 H 0.764661 0.169126 0.684874 0.062 Uiso 1 1 calc R U . . .
C10 C 0.83092(12) 0.20996(18) 0.59844(7) 0.0382(3) Uani 1 1 d . . . . .
C11 C 0.76864(18) 0.7024(2) 0.53304(10) 0.0641(5) Uani 1 1 d . . . . .
H11A H 0.825760 0.804339 0.541644 0.077 Uiso 1 1 calc R U . . .
H11B H 0.686600 0.744620 0.504894 0.077 Uiso 1 1 calc R U . . .
C12 C 0.64616(13) 0.35148(18) 0.34778(7) 0.0408(3) Uani 1 1 d . . . . .
C13 C 1.02902(15) 0.0599(3) 0.61229(11) 0.0645(5) Uani 1 1 d . . . . .
H13 H 1.095960 0.031877 0.594022 0.077 Uiso 1 1 calc R U . . .
C14 C 0.67278(14) 0.4661(2) 0.59423(8) 0.0483(4) Uani 1 1 d . . . . .
H14A H 0.588676 0.503354 0.567417 0.058 Uiso 1 1 calc R U . . .
H14B H 0.669614 0.421190 0.641228 0.058 Uiso 1 1 calc R U . . .
C15 C 1.02683(17) -0.0054(3) 0.67907(11) 0.0716(5) Uani 1 1 d . . . . .
H15 H 1.092361 -0.076887 0.706064 0.086 Uiso 1 1 calc R U . . .
C16 C 0.93182(13) 0.1673(2) 0.57208(8) 0.0484(4) Uani 1 1 d . . . . .
H16 H 0.934185 0.211227 0.527024 0.058 Uiso 1 1 calc R U . . .
C17 C 0.81532(14) 0.5574(2) 0.48967(9) 0.0512(4) Uani 1 1 d . . . . .
H17A H 0.811246 0.602622 0.441561 0.061 Uiso 1 1 calc R U . . .
H17B H 0.901938 0.526951 0.514180 0.061 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 C1 1.2325(15) . ?
O2 C12 1.1988(16) . ?
O3 C5 1.4503(16) . ?
O3 C12 1.3261(17) . ?
N1 H1 0.8600 . ?
N1 C1 1.3392(15) . ?
N1 C4 1.4598(16) . ?
C1 C8 1.4885(17) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 C5 1.489(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C11 1.519(2) . ?
C3 C14 1.520(2) . ?
C4 C6 1.5157(17) . ?
C4 C10 1.5330(18) . ?
C4 C14 1.5413(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C8 1.3370(19) . ?
C6 C17 1.4878(19) . ?
C7 H7 0.9300 . ?
C7 C9 1.377(2) . ?
C7 C15 1.370(3) . ?
C8 C12 1.4802(17) . ?
C9 H9 0.9300 . ?
C9 C10 1.3897(19) . ?
C10 C16 1.389(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C17 1.535(2) . ?
C13 H13 0.9300 . ?
C13 C15 1.375(3) . ?
C13 C16 1.386(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O3 C5 117.48(11) . . ?
C1 N1 H1 123.4 . . ?
C1 N1 C4 113.26(10) . . ?
C4 N1 H1 123.4 . . ?
O1 C1 N1 126.38(11) . . ?
O1 C1 C8 127.27(11) . . ?
N1 C1 C8 106.35(10) . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C5 C2 H2A 109.5 . . ?
C5 C2 H2B 109.5 . . ?
C5 C2 H2C 109.5 . . ?
H3A C3 H3B 108.0 . . ?
C11 C3 H3A 109.4 . . ?
C11 C3 H3B 109.4 . . ?
C11 C3 C14 111.01(13) . . ?
C14 C3 H3A 109.4 . . ?
C14 C3 H3B 109.4 . . ?
N1 C4 C6 101.38(10) . . ?
N1 C4 C10 108.43(11) . . ?
N1 C4 C14 111.63(10) . . ?
C6 C4 C10 113.74(10) . . ?
C6 C4 C14 107.55(11) . . ?
C10 C4 C14 113.50(11) . . ?
O3 C5 C2 106.90(12) . . ?
O3 C5 H5A 110.3 . . ?
O3 C5 H5B 110.3 . . ?
C2 C5 H5A 110.3 . . ?
C2 C5 H5B 110.3 . . ?
H5A C5 H5B 108.6 . . ?
C8 C6 C4 109.86(11) . . ?
C8 C6 C17 130.79(12) . . ?
C17 C6 C4 118.67(12) . . ?
C9 C7 H7 119.9 . . ?
C15 C7 H7 119.9 . . ?
C15 C7 C9 120.21(16) . . ?
C6 C8 C1 109.07(11) . . ?
C6 C8 C12 127.62(12) . . ?
C12 C8 C1 123.30(11) . . ?
C7 C9 H9 119.4 . . ?
C7 C9 C10 121.22(15) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C4 119.96(12) . . ?
C16 C10 C4 121.90(12) . . ?
C16 C10 C9 117.89(13) . . ?
C3 C11 H11A 109.4 . . ?
C3 C11 H11B 109.4 . . ?
C3 C11 C17 111.10(14) . . ?
H11A C11 H11B 108.0 . . ?
C17 C11 H11A 109.4 . . ?
C17 C11 H11B 109.4 . . ?
O2 C12 O3 124.06(13) . . ?
O2 C12 C8 124.81(13) . . ?
O3 C12 C8 111.12(11) . . ?
C15 C13 H13 119.9 . . ?
C15 C13 C16 120.24(16) . . ?
C16 C13 H13 119.9 . . ?
C3 C14 C4 111.95(12) . . ?
C3 C14 H14A 109.2 . . ?
C3 C14 H14B 109.2 . . ?
C4 C14 H14A 109.2 . . ?
C4 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C7 C15 C13 119.81(16) . . ?
C7 C15 H15 120.1 . . ?
C13 C15 H15 120.1 . . ?
C10 C16 H16 119.7 . . ?
C13 C16 C10 120.63(15) . . ?
C13 C16 H16 119.7 . . ?
C6 C17 C11 108.89(12) . . ?
C6 C17 H17A 109.9 . . ?
C6 C17 H17B 109.9 . . ?
C11 C17 H17A 109.9 . . ?
C11 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C8 C6 -178.84(13) . . . . ?
O1 C1 C8 C12 1.9(2) . . . . ?
N1 C1 C8 C6 0.94(15) . . . . ?
N1 C1 C8 C12 -178.36(12) . . . . ?
N1 C4 C6 C8 -2.11(14) . . . . ?
N1 C4 C6 C17 169.42(11) . . . . ?
N1 C4 C10 C9 -73.60(15) . . . . ?
N1 C4 C10 C16 100.57(14) . . . . ?
N1 C4 C14 C3 -162.64(12) . . . . ?
C1 N1 C4 C6 2.81(14) . . . . ?
C1 N1 C4 C10 -117.19(12) . . . . ?
C1 N1 C4 C14 117.06(13) . . . . ?
C1 C8 C12 O2 -138.99(16) . . . . ?
C1 C8 C12 O3 40.23(17) . . . . ?
C3 C11 C17 C6 53.16(18) . . . . ?
C4 N1 C1 O1 177.35(13) . . . . ?
C4 N1 C1 C8 -2.43(15) . . . . ?
C4 C6 C8 C1 0.83(15) . . . . ?
C4 C6 C8 C12 -179.91(12) . . . . ?
C4 C6 C17 C11 -52.98(17) . . . . ?
C4 C10 C16 C13 -174.13(14) . . . . ?
C5 O3 C12 O2 5.1(2) . . . . ?
C5 O3 C12 C8 -174.11(12) . . . . ?
C6 C4 C10 C9 174.45(12) . . . . ?
C6 C4 C10 C16 -11.39(18) . . . . ?
C6 C4 C14 C3 -52.27(15) . . . . ?
C6 C8 C12 O2 41.9(2) . . . . ?
C6 C8 C12 O3 -138.93(14) . . . . ?
C7 C9 C10 C4 174.18(15) . . . . ?
C7 C9 C10 C16 -0.2(2) . . . . ?
C8 C6 C17 C11 116.47(17) . . . . ?
C9 C7 C15 C13 -0.4(3) . . . . ?
C9 C10 C16 C13 0.1(2) . . . . ?
C10 C4 C6 C8 114.05(12) . . . . ?
C10 C4 C6 C17 -74.42(15) . . . . ?
C10 C4 C14 C3 74.45(16) . . . . ?
C11 C3 C14 C4 58.42(18) . . . . ?
C12 O3 C5 C2 -178.68(14) . . . . ?
C14 C3 C11 C17 -58.15(19) . . . . ?
C14 C4 C6 C8 -119.37(12) . . . . ?
C14 C4 C6 C17 52.16(15) . . . . ?
C14 C4 C10 C9 51.06(17) . . . . ?
C14 C4 C10 C16 -134.78(14) . . . . ?
C15 C7 C9 C10 0.3(3) . . . . ?
C15 C13 C16 C10 -0.2(3) . . . . ?
C16 C13 C15 C7 0.3(3) . . . . ?
C17 C6 C8 C1 -169.34(13) . . . . ?
C17 C6 C8 C12 9.9(2) . . . . ?

_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 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.786
####################################################################### 
# 
# 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_chenyut2_1209_autored
_database_code_depnum_ccdc_archive 'CCDC 2470263'
loop_
_audit_author_name
_audit_author_address
'yuting chen'
;Lanzhou university
China
;
_audit_update_record             
;
2025-07-06 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;
_audit_creation_date             2024-12-13
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O2'
_chemical_formula_sum            'C19 H21 N O2'
_chemical_formula_weight         295.37
_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           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                   20.5269(2)
_cell_length_b                   6.68550(10)
_cell_length_c                   24.6306(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.611(2)
_cell_angle_gamma                90
_cell_volume                     3073.06(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    25385
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.0420
_cell_measurement_theta_min      2.3500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            36404
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.171
_diffrn_reflns_theta_min         2.368
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  27.00   0.50    0.05    --  -44.63  57.00 -60.00  176
  2  ω    -70.00 -26.00   0.50    0.05    -- -100.00  61.00   0.00   88
  3  ω    -53.00 -27.00   0.50    0.05    -- -100.00  45.00   0.00   52
  4  ω    -53.00 -27.00   0.50    0.05    -- -100.00  45.00 150.00   52
  5  ω   -175.00 -77.00   0.50    0.05    -- -100.00  -9.00  40.00  196
  6  ω   -106.00 -81.00   0.50    0.05    --  -44.63-141.00 167.00   50
  7  ω    -33.00  11.00   0.50    0.05    --   44.63 -19.00 -30.00   88
  8  ω     -3.00  22.00   0.50    0.05    --   44.63 -19.00-150.00   50
  9  ω     40.00  66.00   0.50    0.05    --  108.93 -61.00 -60.00   52
 10  ω     38.00  72.00   0.50    0.05    --  108.93-129.00 -20.00   68
 11  ω     79.00 114.00   0.50    0.05    --  108.93-129.00 -20.00   70
 12  ω     99.00 125.00   0.50    0.05    --  108.93-153.00  85.00   52
 13  ω     54.00  93.00   0.50    0.05    --  108.93-153.00  85.00   78
 14  ω     64.00 118.00   0.50    0.05    --   44.63 153.00 126.00  108
 15  ω    -90.00 -56.00   0.50    0.05    --  -44.63 179.00-180.00   68
 16  ω   -116.00 -48.00   0.50    0.05    --  -44.63-179.00  30.00  136
 17  ω    -28.00  34.00   0.50    0.05    --  -44.63  19.00-180.00  124
 18  ω    -28.00  32.00   0.50    0.05    --  -44.63  19.00-120.00  120
 19  ω    -33.00  -8.00   0.50    0.05    --   44.63 -19.00  60.00   50
 20  ω      5.00  38.00   0.50    0.05    --   44.63 -37.00 150.00   66
 21  ω     -3.00  23.00   0.50    0.05    --   44.63 -19.00-150.00   52
 22  ω    -93.00 -63.00   0.50    0.05    -- -100.00 125.00-150.00   60
 23  ω    -75.00 -49.00   0.50    0.05    -- -100.00 141.00 128.06   52
 24  ω    -54.00 -29.00   0.50    0.05    -- -100.00  45.00 -90.00   50
 25  ω    -51.00 -25.00   0.50    0.05    -- -100.00  45.00 -60.00   52
 26  ω   -123.00 -92.00   0.50    0.05    -- -100.00 141.00 128.06   62
 27  ω   -174.00-149.00   0.50    0.05    -- -100.00 -94.00 150.00   50
 28  ω   -124.00 -87.00   0.50    0.05    -- -100.00 -94.00 150.00   74
 29  ω   -109.00 -80.00   0.50    0.05    -- -100.00 115.00-107.38   58
 30  ω    -85.00 -34.00   0.50    0.05    -- -100.00 142.00 -19.89  102
 31  ω    -52.00 -26.00   0.50    0.05    -- -100.00  45.00 120.00   52
 32  ω    -68.00 -36.00   0.50    0.05    -- -100.00  61.00-120.00   64
 33  ω   -168.00-108.00   0.50    0.05    -- -100.00-120.00-116.00  120
 34  ω   -124.00 -98.00   0.50    0.05    -- -100.00 142.00 -19.89   52
 35  ω    -60.00 -35.00   0.50    0.05    -- -100.00 151.00  85.51   50
 36  ω   -101.00 -75.00   0.50    0.05    -- -100.00 151.00  85.51   52
 37  ω    -58.00 -33.00   0.50    0.05    -- -100.00 125.00-150.00   50
 38  ω    -53.00 -27.00   0.50    0.05    -- -100.00  45.00  90.00   52
 39  ω    -84.00 -50.00   0.50    0.05    -- -100.00  77.00-120.00   68
 40  ω    -62.00 -35.00   0.50    0.05    -- -100.00  61.00 -30.00   54
 41  ω   -112.00 -29.00   0.50    0.05    -- -100.00 125.00 150.00  166
 42  ω   -122.00 -97.00   0.50    0.05    -- -100.00 139.00  56.01   50
 43  ω    -84.00 -34.00   0.50    0.05    -- -100.00 139.00  56.01  100
 44  ω     81.00 107.00   0.50    0.05    --  108.93-125.00   0.00   52
 45  ω     40.00  66.00   0.50    0.05    --  108.93-125.00   0.00   52
 46  ω    138.00 170.00   0.50    0.05    --  108.93  61.00-150.00   64
 47  ω    100.00 154.00   0.50    0.05    --  108.93  45.00-120.00  108
 48  ω     98.00 134.00   0.50    0.05    --  108.93  61.00-150.00   72
 49  ω     65.00  90.00   0.50    0.05    --  108.93 -77.00  30.00   50
 50  ω     40.00 103.00   0.50    0.05    --  108.93 -77.00  60.00  126
 51  ω     35.00  60.00   0.50    0.05    --  108.93 -61.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0627086000
_diffrn_orient_matrix_UB_12      -0.0170566000
_diffrn_orient_matrix_UB_13      -0.0186668000
_diffrn_orient_matrix_UB_21      0.0536901000
_diffrn_orient_matrix_UB_22      0.0221113000
_diffrn_orient_matrix_UB_23      0.0657438000
_diffrn_orient_matrix_UB_31      0.0005239000
_diffrn_orient_matrix_UB_32      -0.2287475000
_diffrn_orient_matrix_UB_33      0.0077464000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5430
_reflns_number_total             6133
_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 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²+0.8054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1187
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C56(H56)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C18(H18A,H18B), C21(H21A,H21B), C23(H23A,
 H23B), C24(H24A,H24B), C35(H35A,H35B), C44(H44A,H44B), C54(H54A,H54B),
 C57(H57A,H57B), C63(H63A,H63B), C64(H64A,H64B), C67(H67A,H67B), C76(H76A,H76B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C14(H14), C15(H15), C26(H26), C28(H28), C39(H39), N47(H47), C58(H58),
 C59(H59), C69(H69), C71(H71), C82(H82)
;
_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 0.42390(5) 0.16940(14) 0.98557(4) 0.0291(2) Uani 1 1 d . . . . .
O12 O 0.26519(5) 0.38743(15) 0.82637(4) 0.0328(2) Uani 1 1 d . . . . .
N4 N 0.48104(5) 0.08627(16) 0.92557(4) 0.0251(2) Uani 1 1 d . . . . .
H4 H 0.511959 0.000119 0.949748 0.030 Uiso 1 1 calc R U . . .
C1 C 0.38476(6) 0.29265(18) 0.88326(5) 0.0232(3) Uani 1 1 d . . . . .
C3 C 0.43075(6) 0.17938(18) 0.93817(5) 0.0233(3) Uani 1 1 d . . . . .
C6 C 0.47889(6) 0.14316(18) 0.86770(5) 0.0238(3) Uani 1 1 d . . . . .
C7 C 0.41427(6) 0.28077(18) 0.84402(5) 0.0231(3) Uani 1 1 d . . . . .
C8 C 0.31680(6) 0.39615(18) 0.87459(5) 0.0240(3) Uani 1 1 d . . . . .
C9 C 0.54909(6) 0.2475(2) 0.87699(5) 0.0261(3) Uani 1 1 d . . . . .
C10 C 0.45904(7) -0.0338(2) 0.82314(6) 0.0303(3) Uani 1 1 d . . . . .
H10A H 0.500159 -0.126879 0.834910 0.036 Uiso 1 1 calc R U . . .
H10B H 0.418047 -0.107793 0.824650 0.036 Uiso 1 1 calc R U . . .
C11 C 0.39031(7) 0.3611(2) 0.78225(5) 0.0272(3) Uani 1 1 d . . . . .
H11A H 0.427840 0.448901 0.779829 0.033 Uiso 1 1 calc R U . . .
H11B H 0.346096 0.441058 0.771623 0.033 Uiso 1 1 calc R U . . .
C13 C 0.31798(6) 0.51779(19) 0.92560(6) 0.0259(3) Uani 1 1 d . . . . .
H13 H 0.330801 0.433568 0.962160 0.031 Uiso 1 1 calc R U . . .
C14 C 0.56093(7) 0.4436(2) 0.89838(6) 0.0315(3) Uani 1 1 d . . . . .
H14 H 0.524389 0.511893 0.905130 0.038 Uiso 1 1 calc R U . . .
C15 C 0.60401(7) 0.1500(2) 0.86849(6) 0.0332(3) Uani 1 1 d . . . . .
H15 H 0.597464 0.015875 0.854507 0.040 Uiso 1 1 calc R U . . .
C18 C 0.43919(8) 0.0398(2) 0.75927(6) 0.0336(3) Uani 1 1 d . . . . .
H18A H 0.481096 0.107431 0.757383 0.040 Uiso 1 1 calc R U . . .
H18B H 0.426806 -0.076422 0.731903 0.040 Uiso 1 1 calc R U . . .
C21 C 0.37591(7) 0.1847(2) 0.73870(6) 0.0323(3) Uani 1 1 d . . . . .
H21A H 0.332420 0.112547 0.735685 0.039 Uiso 1 1 calc R U . . .
H21B H 0.366950 0.236393 0.698535 0.039 Uiso 1 1 calc R U . . .
C23 C 0.25443(7) 0.6555(2) 0.91649(7) 0.0342(3) Uani 1 1 d . . . . .
H23A H 0.225384 0.610901 0.937788 0.041 Uiso 1 1 calc R U . . .
H23B H 0.223677 0.685323 0.874078 0.041 Uiso 1 1 calc R U . . .
C24 C 0.36690(7) 0.7056(2) 0.93907(7) 0.0363(3) Uani 1 1 d . . . . .
H24A H 0.412309 0.693180 0.975331 0.044 Uiso 1 1 calc R U . . .
H24B H 0.375675 0.752831 0.904603 0.044 Uiso 1 1 calc R U . . .
C26 C 0.62516(8) 0.5407(2) 0.90995(6) 0.0401(4) Uani 1 1 d . . . . .
H26 H 0.632214 0.674412 0.924345 0.048 Uiso 1 1 calc R U . . .
C28 C 0.66872(7) 0.2477(3) 0.88035(7) 0.0435(4) Uani 1 1 d . . . . .
H28 H 0.705907 0.179514 0.874517 0.052 Uiso 1 1 calc R U . . .
C35 C 0.30821(8) 0.8226(2) 0.94884(8) 0.0447(4) Uani 1 1 d . . . . .
H35A H 0.296483 0.952980 0.927885 0.054 Uiso 1 1 calc R U . . .
H35B H 0.317391 0.838043 0.991392 0.054 Uiso 1 1 calc R U . . .
C39 C 0.67881(8) 0.4428(3) 0.90050(7) 0.0459(4) Uani 1 1 d . . . . .
H39 H 0.722542 0.509577 0.907861 0.055 Uiso 1 1 calc R U . . .
O45 O 0.04307(5) 0.77052(14) 0.48544(4) 0.0311(2) Uani 1 1 d . . . . .
O55 O 0.20243(5) 0.36670(15) 0.60438(4) 0.0334(2) Uani 1 1 d . . . . .
N47 N 0.05387(6) 0.91582(17) 0.57316(5) 0.0288(2) Uani 1 1 d . . . . .
H47 H 0.028090 1.023277 0.557560 0.035 Uiso 1 1 calc R U . . .
C44 C 0.18745(7) 0.9646(2) 0.73606(6) 0.0324(3) Uani 1 1 d . . . . .
H44A H 0.221585 1.071615 0.758077 0.039 Uiso 1 1 calc R U . . .
H44B H 0.156737 0.936260 0.757255 0.039 Uiso 1 1 calc R U . . .
C46 C 0.06735(6) 0.77421(19) 0.54049(5) 0.0256(3) Uani 1 1 d . . . . .
C48 C 0.11791(6) 0.62816(18) 0.58411(5) 0.0242(3) Uani 1 1 d . . . . .
C50 C 0.08620(7) 0.87363(19) 0.63697(5) 0.0257(3) Uani 1 1 d . . . . .
C51 C 0.15036(6) 0.45225(19) 0.56705(5) 0.0243(3) Uani 1 1 d . . . . .
C52 C 0.12835(6) 0.68474(18) 0.63959(5) 0.0242(3) Uani 1 1 d . . . . .
C53 C 0.02622(7) 0.8469(2) 0.65797(5) 0.0270(3) Uani 1 1 d . . . . .
C54 C 0.14090(7) 1.0356(2) 0.67263(6) 0.0307(3) Uani 1 1 d . . . . .
H54A H 0.171858 1.068188 0.651953 0.037 Uiso 1 1 calc R U . . .
H54B H 0.115066 1.158782 0.674364 0.037 Uiso 1 1 calc R U . . .
C56 C 0.11906(6) 0.39396(19) 0.50246(6) 0.0261(3) Uani 1 1 d . . . . .
H56 H 0.065738 0.406614 0.481920 0.031 Uiso 1 1 calc R U . . .
C57 C 0.17771(7) 0.6067(2) 0.69971(6) 0.0283(3) Uani 1 1 d . . . . .
H57A H 0.205634 0.492359 0.695099 0.034 Uiso 1 1 calc R U . . .
H57B H 0.149627 0.559894 0.721605 0.034 Uiso 1 1 calc R U . . .
C58 C 0.00217(8) 0.6593(2) 0.66569(7) 0.0363(3) Uani 1 1 d . . . . .
H58 H 0.025439 0.542862 0.660411 0.044 Uiso 1 1 calc R U . . .
C59 C -0.01022(7) 1.0135(2) 0.66487(7) 0.0377(3) Uani 1 1 d . . . . .
H59 H 0.004630 1.143557 0.659306 0.045 Uiso 1 1 calc R U . . .
C63 C 0.14878(7) 0.1981(2) 0.48845(6) 0.0316(3) Uani 1 1 d . . . . .
H63A H 0.171347 0.108859 0.523419 0.038 Uiso 1 1 calc R U . . .
H63B H 0.113610 0.124128 0.453825 0.038 Uiso 1 1 calc R U . . .
C64 C 0.16021(7) 0.5121(2) 0.47159(6) 0.0314(3) Uani 1 1 d . . . . .
H64A H 0.129347 0.557559 0.430608 0.038 Uiso 1 1 calc R U . . .
H64B H 0.189963 0.623137 0.495999 0.038 Uiso 1 1 calc R U . . .
C67 C 0.22880(7) 0.7764(2) 0.73482(6) 0.0315(3) Uani 1 1 d . . . . .
H67A H 0.257855 0.731366 0.776243 0.038 Uiso 1 1 calc R U . . .
H67B H 0.261907 0.807506 0.716065 0.038 Uiso 1 1 calc R U . . .
C69 C -0.05541(8) 0.6396(3) 0.68103(7) 0.0442(4) Uani 1 1 d . . . . .
H69 H -0.070610 0.510105 0.686671 0.053 Uiso 1 1 calc R U . . .
C71 C -0.06807(8) 0.9920(3) 0.67980(7) 0.0462(4) Uani 1 1 d . . . . .
H71 H -0.092314 1.107511 0.684299 0.055 Uiso 1 1 calc R U . . .
C76 C 0.20293(8) 0.3202(2) 0.47379(7) 0.0364(3) Uani 1 1 d . . . . .
H76A H 0.203667 0.284803 0.435028 0.044 Uiso 1 1 calc R U . . .
H76B H 0.251959 0.320051 0.506158 0.044 Uiso 1 1 calc R U . . .
C82 C -0.09066(8) 0.8056(3) 0.68813(7) 0.0441(4) Uani 1 1 d . . . . .
H82 H -0.130021 0.791686 0.698640 0.053 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 C3 1.2346(15) . ?
O12 C8 1.2199(15) . ?
N4 H4 0.8800 . ?
N4 C3 1.3477(16) . ?
N4 C6 1.4579(15) . ?
C1 C3 1.4935(16) . ?
C1 C7 1.3396(18) . ?
C1 C8 1.4906(17) . ?
C6 C7 1.5171(16) . ?
C6 C9 1.5300(17) . ?
C6 C10 1.5485(17) . ?
C7 C11 1.4906(16) . ?
C8 C13 1.4883(18) . ?
C9 C14 1.396(2) . ?
C9 C15 1.3915(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C18 1.5326(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C21 1.5377(18) . ?
C13 H13 1.0000 . ?
C13 C23 1.5350(18) . ?
C13 C24 1.5549(19) . ?
C14 H14 0.9500 . ?
C14 C26 1.3885(19) . ?
C15 H15 0.9500 . ?
C15 C28 1.397(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C21 1.5278(19) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C35 1.539(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C35 1.537(2) . ?
C26 H26 0.9500 . ?
C26 C39 1.382(2) . ?
C28 H28 0.9500 . ?
C28 C39 1.380(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C39 H39 0.9500 . ?
O45 C46 1.2347(15) . ?
O55 C51 1.2234(15) . ?
N47 H47 0.8800 . ?
N47 C46 1.3437(17) . ?
N47 C50 1.4567(16) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C44 C54 1.5282(19) . ?
C44 C67 1.5256(19) . ?
C46 C48 1.5020(16) . ?
C48 C51 1.4955(17) . ?
C48 C52 1.3461(18) . ?
C50 C52 1.5169(17) . ?
C50 C53 1.5316(18) . ?
C50 C54 1.5438(18) . ?
C51 C56 1.4981(17) . ?
C52 C57 1.4973(16) . ?
C53 C58 1.390(2) . ?
C53 C59 1.3913(19) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C56 H56 1.0000 . ?
C56 C63 1.5431(18) . ?
C56 C64 1.5652(18) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C57 C67 1.5424(18) . ?
C58 H58 0.9500 . ?
C58 C69 1.389(2) . ?
C59 H59 0.9500 . ?
C59 C71 1.389(2) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C63 C76 1.538(2) . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C64 C76 1.5417(19) . ?
C67 H67A 0.9900 . ?
C67 H67B 0.9900 . ?
C69 H69 0.9500 . ?
C69 C82 1.375(2) . ?
C71 H71 0.9500 . ?
C71 C82 1.374(3) . ?
C76 H76A 0.9900 . ?
C76 H76B 0.9900 . ?
C82 H82 0.9500 . ?

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 N4 H4 123.5 . . ?
C3 N4 C6 112.98(10) . . ?
C6 N4 H4 123.5 . . ?
C7 C1 C3 108.54(11) . . ?
C7 C1 C8 126.98(11) . . ?
C8 C1 C3 124.47(11) . . ?
O2 C3 N4 126.35(11) . . ?
O2 C3 C1 127.29(11) . . ?
N4 C3 C1 106.36(10) . . ?
N4 C6 C7 101.52(9) . . ?
N4 C6 C9 109.24(10) . . ?
N4 C6 C10 112.67(10) . . ?
C7 C6 C9 113.53(10) . . ?
C7 C6 C10 105.13(10) . . ?
C9 C6 C10 114.07(11) . . ?
C1 C7 C6 110.14(10) . . ?
C1 C7 C11 131.21(11) . . ?
C11 C7 C6 118.35(11) . . ?
O12 C8 C1 119.91(11) . . ?
O12 C8 C13 123.38(11) . . ?
C13 C8 C1 116.58(10) . . ?
C14 C9 C6 119.33(11) . . ?
C15 C9 C6 122.38(12) . . ?
C15 C9 C14 118.16(12) . . ?
C6 C10 H10A 109.4 . . ?
C6 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C18 C10 C6 111.18(11) . . ?
C18 C10 H10A 109.4 . . ?
C18 C10 H10B 109.4 . . ?
C7 C11 H11A 109.9 . . ?
C7 C11 H11B 109.9 . . ?
C7 C11 C21 108.77(11) . . ?
H11A C11 H11B 108.3 . . ?
C21 C11 H11A 109.9 . . ?
C21 C11 H11B 109.9 . . ?
C8 C13 H13 111.0 . . ?
C8 C13 C23 119.36(11) . . ?
C8 C13 C24 113.80(11) . . ?
C23 C13 H13 111.0 . . ?
C23 C13 C24 88.90(10) . . ?
C24 C13 H13 111.0 . . ?
C9 C14 H14 119.4 . . ?
C26 C14 C9 121.19(14) . . ?
C26 C14 H14 119.4 . . ?
C9 C15 H15 119.7 . . ?
C9 C15 C28 120.59(15) . . ?
C28 C15 H15 119.7 . . ?
C10 C18 H18A 109.3 . . ?
C10 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C21 C18 C10 111.71(11) . . ?
C21 C18 H18A 109.3 . . ?
C21 C18 H18B 109.3 . . ?
C11 C21 H21A 109.3 . . ?
C11 C21 H21B 109.3 . . ?
C18 C21 C11 111.40(10) . . ?
C18 C21 H21A 109.3 . . ?
C18 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C13 C23 H23A 113.9 . . ?
C13 C23 H23B 113.9 . . ?
C13 C23 C35 88.68(10) . . ?
H23A C23 H23B 111.1 . . ?
C35 C23 H23A 113.9 . . ?
C35 C23 H23B 113.9 . . ?
C13 C24 H24A 114.0 . . ?
C13 C24 H24B 114.0 . . ?
H24A C24 H24B 111.2 . . ?
C35 C24 C13 88.05(11) . . ?
C35 C24 H24A 114.0 . . ?
C35 C24 H24B 114.0 . . ?
C14 C26 H26 120.0 . . ?
C39 C26 C14 119.94(15) . . ?
C39 C26 H26 120.0 . . ?
C15 C28 H28 119.9 . . ?
C39 C28 C15 120.27(15) . . ?
C39 C28 H28 119.9 . . ?
C23 C35 H35A 113.7 . . ?
C23 C35 H35B 113.7 . . ?
C24 C35 C23 89.39(11) . . ?
C24 C35 H35A 113.7 . . ?
C24 C35 H35B 113.7 . . ?
H35A C35 H35B 111.0 . . ?
C26 C39 H39 120.1 . . ?
C28 C39 C26 119.85(14) . . ?
C28 C39 H39 120.1 . . ?
C46 N47 H47 123.4 . . ?
C46 N47 C50 113.25(10) . . ?
C50 N47 H47 123.4 . . ?
H44A C44 H44B 108.1 . . ?
C54 C44 H44A 109.5 . . ?
C54 C44 H44B 109.5 . . ?
C67 C44 H44A 109.5 . . ?
C67 C44 H44B 109.5 . . ?
C67 C44 C54 110.61(11) . . ?
O45 C46 N47 125.59(11) . . ?
O45 C46 C48 127.96(12) . . ?
N47 C46 C48 106.44(10) . . ?
C51 C48 C46 124.48(11) . . ?
C52 C48 C46 108.29(11) . . ?
C52 C48 C51 127.23(11) . . ?
N47 C50 C52 101.68(10) . . ?
N47 C50 C53 108.53(10) . . ?
N47 C50 C54 112.00(11) . . ?
C52 C50 C53 114.39(10) . . ?
C52 C50 C54 107.04(10) . . ?
C53 C50 C54 112.73(11) . . ?
O55 C51 C48 120.56(12) . . ?
O55 C51 C56 122.05(12) . . ?
C48 C51 C56 117.31(10) . . ?
C48 C52 C50 110.12(10) . . ?
C48 C52 C57 131.46(12) . . ?
C57 C52 C50 118.10(11) . . ?
C58 C53 C50 122.22(12) . . ?
C58 C53 C59 117.79(13) . . ?
C59 C53 C50 119.76(12) . . ?
C44 C54 C50 111.14(11) . . ?
C44 C54 H54A 109.4 . . ?
C44 C54 H54B 109.4 . . ?
C50 C54 H54A 109.4 . . ?
C50 C54 H54B 109.4 . . ?
H54A C54 H54B 108.0 . . ?
C51 C56 H56 114.2 . . ?
C51 C56 C63 115.06(10) . . ?
C51 C56 C64 107.76(10) . . ?
C63 C56 H56 114.2 . . ?
C63 C56 C64 88.62(10) . . ?
C64 C56 H56 114.2 . . ?
C52 C57 H57A 110.0 . . ?
C52 C57 H57B 110.0 . . ?
C52 C57 C67 108.69(11) . . ?
H57A C57 H57B 108.3 . . ?
C67 C57 H57A 110.0 . . ?
C67 C57 H57B 110.0 . . ?
C53 C58 H58 119.5 . . ?
C69 C58 C53 120.91(15) . . ?
C69 C58 H58 119.5 . . ?
C53 C59 H59 119.6 . . ?
C71 C59 C53 120.78(15) . . ?
C71 C59 H59 119.6 . . ?
C56 C63 H63A 113.7 . . ?
C56 C63 H63B 113.7 . . ?
H63A C63 H63B 111.0 . . ?
C76 C63 C56 89.63(10) . . ?
C76 C63 H63A 113.7 . . ?
C76 C63 H63B 113.7 . . ?
C56 C64 H64A 113.9 . . ?
C56 C64 H64B 113.9 . . ?
H64A C64 H64B 111.1 . . ?
C76 C64 C56 88.70(10) . . ?
C76 C64 H64A 113.9 . . ?
C76 C64 H64B 113.9 . . ?
C44 C67 C57 111.34(10) . . ?
C44 C67 H67A 109.4 . . ?
C44 C67 H67B 109.4 . . ?
C57 C67 H67A 109.4 . . ?
C57 C67 H67B 109.4 . . ?
H67A C67 H67B 108.0 . . ?
C58 C69 H69 119.6 . . ?
C82 C69 C58 120.71(16) . . ?
C82 C69 H69 119.6 . . ?
C59 C71 H71 119.6 . . ?
C82 C71 C59 120.82(15) . . ?
C82 C71 H71 119.6 . . ?
C63 C76 C64 89.65(10) . . ?
C63 C76 H76A 113.7 . . ?
C63 C76 H76B 113.7 . . ?
C64 C76 H76A 113.7 . . ?
C64 C76 H76B 113.7 . . ?
H76A C76 H76B 111.0 . . ?
C69 C82 H82 120.5 . . ?
C71 C82 C69 118.97(14) . . ?
C71 C82 H82 120.5 . . ?

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
O12 C8 C13 C23 -5.85(19) . . . . ?
O12 C8 C13 C24 -108.80(14) . . . . ?
N4 C6 C7 C1 -1.21(13) . . . . ?
N4 C6 C7 C11 -175.59(10) . . . . ?
N4 C6 C9 C14 -74.87(14) . . . . ?
N4 C6 C9 C15 100.98(13) . . . . ?
N4 C6 C10 C18 165.99(10) . . . . ?
C1 C7 C11 C21 -117.01(15) . . . . ?
C1 C8 C13 C23 170.01(11) . . . . ?
C1 C8 C13 C24 67.07(14) . . . . ?
C3 N4 C6 C7 -3.49(13) . . . . ?
C3 N4 C6 C9 116.69(11) . . . . ?
C3 N4 C6 C10 -115.44(12) . . . . ?
C3 C1 C7 C6 4.94(14) . . . . ?
C3 C1 C7 C11 178.36(12) . . . . ?
C3 C1 C8 O12 -139.12(13) . . . . ?
C3 C1 C8 C13 44.86(17) . . . . ?
C6 N4 C3 O2 -174.61(12) . . . . ?
C6 N4 C3 C1 6.41(13) . . . . ?
C6 C7 C11 C21 55.97(14) . . . . ?
C6 C9 C14 C26 177.12(12) . . . . ?
C6 C9 C15 C28 -176.76(12) . . . . ?
C6 C10 C18 C21 -58.97(15) . . . . ?
C7 C1 C3 O2 173.99(12) . . . . ?
C7 C1 C3 N4 -7.04(14) . . . . ?
C7 C1 C8 O12 39.44(19) . . . . ?
C7 C1 C8 C13 -136.58(13) . . . . ?
C7 C6 C9 C14 37.62(15) . . . . ?
C7 C6 C9 C15 -146.53(12) . . . . ?
C7 C6 C10 C18 56.29(13) . . . . ?
C7 C11 C21 C18 -50.73(15) . . . . ?
C8 C1 C3 O2 -7.2(2) . . . . ?
C8 C1 C3 N4 171.75(11) . . . . ?
C8 C1 C7 C6 -173.80(11) . . . . ?
C8 C1 C7 C11 -0.4(2) . . . . ?
C8 C13 C23 C35 -133.60(13) . . . . ?
C8 C13 C24 C35 138.58(12) . . . . ?
C9 C6 C7 C1 -118.31(12) . . . . ?
C9 C6 C7 C11 67.31(14) . . . . ?
C9 C6 C10 C18 -68.73(14) . . . . ?
C9 C14 C26 C39 -0.2(2) . . . . ?
C9 C15 C28 C39 -0.2(2) . . . . ?
C10 C6 C7 C1 116.34(12) . . . . ?
C10 C6 C7 C11 -58.04(14) . . . . ?
C10 C6 C9 C14 158.04(11) . . . . ?
C10 C6 C9 C15 -26.11(16) . . . . ?
C10 C18 C21 C11 54.95(15) . . . . ?
C13 C23 C35 C24 16.91(12) . . . . ?
C13 C24 C35 C23 -16.69(12) . . . . ?
C14 C9 C15 C28 -0.87(19) . . . . ?
C14 C26 C39 C28 -0.9(2) . . . . ?
C15 C9 C14 C26 1.09(19) . . . . ?
C15 C28 C39 C26 1.1(2) . . . . ?
C23 C13 C24 C35 16.75(12) . . . . ?
C24 C13 C23 C35 -16.71(12) . . . . ?
O45 C46 C48 C51 2.6(2) . . . . ?
O45 C46 C48 C52 -177.75(13) . . . . ?
O55 C51 C56 C63 9.86(18) . . . . ?
O55 C51 C56 C64 -87.14(14) . . . . ?
N47 C46 C48 C51 -176.32(11) . . . . ?
N47 C46 C48 C52 3.34(14) . . . . ?
N47 C50 C52 C48 -2.06(13) . . . . ?
N47 C50 C52 C57 172.22(11) . . . . ?
N47 C50 C53 C58 98.96(14) . . . . ?
N47 C50 C53 C59 -75.39(14) . . . . ?
N47 C50 C54 C44 -165.72(11) . . . . ?
C46 N47 C50 C52 4.39(14) . . . . ?
C46 N47 C50 C53 -116.55(12) . . . . ?
C46 N47 C50 C54 118.35(12) . . . . ?
C46 C48 C51 O55 163.59(12) . . . . ?
C46 C48 C51 C56 -13.16(17) . . . . ?
C46 C48 C52 C50 -0.62(14) . . . . ?
C46 C48 C52 C57 -173.88(13) . . . . ?
C48 C51 C56 C63 -173.44(11) . . . . ?
C48 C51 C56 C64 89.55(13) . . . . ?
C48 C52 C57 C67 119.29(15) . . . . ?
C50 N47 C46 O45 176.17(12) . . . . ?
C50 N47 C46 C48 -4.88(14) . . . . ?
C50 C52 C57 C67 -53.53(15) . . . . ?
C50 C53 C58 C69 -175.78(13) . . . . ?
C50 C53 C59 C71 175.46(13) . . . . ?
C51 C48 C52 C50 179.03(11) . . . . ?
C51 C48 C52 C57 5.8(2) . . . . ?
C51 C56 C63 C76 -95.17(12) . . . . ?
C51 C56 C64 C76 102.12(11) . . . . ?
C52 C48 C51 O55 -16.0(2) . . . . ?
C52 C48 C51 C56 167.24(12) . . . . ?
C52 C50 C53 C58 -13.78(17) . . . . ?
C52 C50 C53 C59 171.87(11) . . . . ?
C52 C50 C54 C44 -55.10(14) . . . . ?
C52 C57 C67 C44 52.49(15) . . . . ?
C53 C50 C52 C48 114.69(12) . . . . ?
C53 C50 C52 C57 -71.03(14) . . . . ?
C53 C50 C54 C44 71.53(14) . . . . ?
C53 C58 C69 C82 0.9(2) . . . . ?
C53 C59 C71 C82 0.0(2) . . . . ?
C54 C44 C67 C57 -57.95(15) . . . . ?
C54 C50 C52 C48 -119.67(12) . . . . ?
C54 C50 C52 C57 54.61(14) . . . . ?
C54 C50 C53 C58 -136.37(13) . . . . ?
C54 C50 C53 C59 49.28(15) . . . . ?
C56 C63 C76 C64 -14.05(10) . . . . ?
C56 C64 C76 C63 13.85(10) . . . . ?
C58 C53 C59 C71 0.9(2) . . . . ?
C58 C69 C82 C71 0.0(2) . . . . ?
C59 C53 C58 C69 -1.3(2) . . . . ?
C59 C71 C82 C69 -0.5(2) . . . . ?
C63 C56 C64 C76 -13.81(10) . . . . ?
C64 C56 C63 C76 13.84(10) . . . . ?
C67 C44 C54 C50 59.87(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.888
_oxdiff_exptl_absorpt_empirical_full_min 0.322
