# Supplementary Information (SI) for Chemical Science.
# 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_zfq-6-1-20240813_auto
_database_code_depnum_ccdc_archive 'CCDC 2403838'
loop_
_audit_author_name
_audit_author_address
'Zhang Fangqing'
;Peking University
China
;
_audit_update_record             
;
2024-11-19 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_audit_creation_date             2024-08-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H34 N2 O4'
_chemical_formula_sum            'C20 H34 N2 O4'
_chemical_formula_weight         366.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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                   26.4619(3)
_cell_length_b                   6.33880(10)
_cell_length_c                   26.1419(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.8770(10)
_cell_angle_gamma                90
_cell_volume                     4291.08(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13927
_cell_measurement_temperature    300.69(10)
_cell_measurement_theta_max      76.8910
_cell_measurement_theta_min      3.3950
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
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    1.135
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            22227
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.061
_diffrn_reflns_theta_min         3.413
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.69(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00 108.00   0.50    0.05    --  105.65 -77.00 150.00  150
  2  ω     79.00 104.00   0.50    0.05    --  105.65 -94.00   0.00   50
  3  ω     80.00 105.00   0.50    0.05    --  105.65 -94.00 -30.00   50
  4  ω     47.00  72.00   0.50    0.05    --  105.65 -61.00  30.00   50
  5  ω     33.00  61.00   0.50    0.05    --  105.65 -94.00 -30.00   56
  6  ω     34.00  64.00   0.50    0.05    --  105.65 -61.00 -90.00   60
  7  ω     43.00  91.00   0.50    0.05    --  105.65 -72.00-106.00   96
  8  ω    -25.00  54.00   0.50    0.05    --   46.54 -72.00-106.00  158
  9  ω    123.00 165.00   0.50    0.05    --  105.65  30.00 -30.00   84
 10  ω    113.00 167.00   0.50    0.05    --  105.65  45.00 -60.00  108
 11  ω    149.00 176.00   0.50    0.05    --  105.65  72.00  23.00   54
 12  ω    141.00 166.00   0.50    0.05    --  105.65  45.00 150.00   50
 13  ω     95.00 120.00   0.50    0.05    --  105.65  45.00 150.00   50
 14  ω     60.00 107.00   0.50    0.05    --   46.54  72.00  23.00   94
 15  ω    -54.00  26.00   0.50    0.05    --  -46.54  72.00  23.00  160
 16  ω    -25.00  28.00   0.50    0.05    --  -46.54  19.00 120.00  106
 17  ω    -15.00  29.00   0.50    0.05    --  -46.54  19.00  30.00   88
 18  ω    -24.00  23.00   0.50    0.05    --  -46.54  19.00   0.00   94
 19  ω    -23.00  29.00   0.50    0.05    --  -46.54  19.00-180.00  104
 20  ω    -69.00 -44.00   0.50    0.05    -- -104.00  61.00-120.00   50
 21  ω    -65.00 -39.00   0.50    0.05    -- -104.00  61.00-150.00   52
 22  ω    -89.00 -31.00   0.50    0.05    -- -104.00  72.00  23.00  116
 23  ω    -66.00 -32.00   0.50    0.05    -- -104.00  61.00  90.00   68
 24  ω    -65.00 -39.00   0.50    0.05    -- -104.00  61.00 150.00   52
 25  ω   -131.00 -90.00   0.50    0.05    -- -104.00 -15.00 150.00   82
 26  ω   -155.00 -92.00   0.50    0.05    -- -104.00 -45.00 150.00  126
 27  ω    -96.00 -71.00   0.50    0.05    --  -46.54 -72.00-106.00   50
 28  ω   -128.00-102.00   0.50    0.05    -- -104.00 -77.00-150.00   52
 29  ω   -171.00-136.00   0.50    0.05    -- -104.00 -77.00-150.00   70
 30  ω   -164.00 -96.00   0.50    0.05    -- -104.00 -72.00-106.00  136
 31  ω   -171.00-101.00   0.50    0.05    -- -104.00 -45.00 -60.00  140
 32  ω   -171.00 -91.00   0.50    0.05    -- -104.00 -30.00  90.00  160
 33  ω   -175.00 -91.00   0.50    0.05    -- -104.00 -30.00 120.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0351754000
_diffrn_orient_matrix_UB_12      0.1466638000
_diffrn_orient_matrix_UB_13      -0.0242258000
_diffrn_orient_matrix_UB_21      0.0475066000
_diffrn_orient_matrix_UB_22      -0.1292810000
_diffrn_orient_matrix_UB_23      0.0265145000
_diffrn_orient_matrix_UB_31      -0.0068273000
_diffrn_orient_matrix_UB_32      -0.1443239000
_diffrn_orient_matrix_UB_33      -0.0483305000
_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                3782
_reflns_number_total             4373
_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 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4373
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0725
_refine_ls_restrained_S_all      1.080
_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)+(0.1390P)²+2.2637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2273
_refine_ls_wR_factor_ref         0.2345
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid bond restraints
 C00A, C00N
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
2.a Ternary CH refined with riding coordinates:
 C00H(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00B(H00D,H00E), C00C(H00F,H00G), C00F(H00H,H00I), C00G(H00J,
 H00K), C00I(H00M,H00N), C00J(H00O,H00P)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00C)
2.d X=CH2 refined with riding coordinates:
 C00N(H00W,H00X)
2.e Idealised Me refined as rotating group:
 C00L(H00Q,H00R,H00S), C00M(H00T,H00U,H00V), C00O(H00Y,H,HA), C00P(H00Z,HB,HC),
  C00Q(H00,HD,HE)
2.f Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.81844(5) 0.1490(2) 0.79437(5) 0.0569(4) Uani 1 1 d . . . . .
H001 H 0.836249 0.060735 0.783417 0.085 Uiso 1 1 calc R U . . .
O002 O 0.47705(6) 0.6794(3) 0.60201(7) 0.0775(5) Uani 1 1 d . . . . .
N003 N 0.61410(6) 0.3959(3) 0.73956(6) 0.0536(4) Uani 1 1 d . . . . .
O004 O 0.79636(8) -0.1289(2) 0.83573(8) 0.0873(6) Uani 1 1 d . . . . .
N005 N 0.53190(6) 0.6319(3) 0.67762(7) 0.0619(5) Uani 1 1 d . . . . .
O006 O 0.47657(8) 0.9093(3) 0.66765(7) 0.0857(6) Uani 1 1 d . . . . .
C007 C 0.79312(7) 0.0588(3) 0.82648(7) 0.0539(4) Uani 1 1 d . . . . .
C008 C 0.75925(7) 0.2079(3) 0.84969(7) 0.0507(4) Uani 1 1 d . . . . .
C009 C 0.72999(7) 0.3695(3) 0.80943(8) 0.0540(5) Uani 1 1 d . . . . .
H00A H 0.737610 0.515397 0.819265 0.065 Uiso 1 1 calc R U . . .
H00B H 0.733894 0.343750 0.773876 0.065 Uiso 1 1 calc R U . . .
C00A C 0.83724(9) 0.4170(4) 0.89223(8) 0.0684(6) Uani 1 1 d . U . . .
H00C H 0.830584 0.525408 0.867797 0.082 Uiso 1 1 calc R U . . .
C00B C 0.58390(8) 0.5469(4) 0.76290(8) 0.0644(5) Uani 1 1 d . . . . .
H00D H 0.605463 0.607985 0.793875 0.077 Uiso 1 1 calc R U . . .
H00E H 0.555448 0.474281 0.773486 0.077 Uiso 1 1 calc R U . . .
C00C C 0.56311(8) 0.7190(4) 0.72521(9) 0.0650(5) Uani 1 1 d . . . . .
H00F H 0.542274 0.814368 0.741271 0.078 Uiso 1 1 calc R U . . .
H00G H 0.591549 0.798941 0.716732 0.078 Uiso 1 1 calc R U . . .
C00D C 0.79091(9) 0.2990(4) 0.90240(7) 0.0639(5) Uani 1 1 d . . . . .
C00E C 0.49345(8) 0.7539(4) 0.64998(8) 0.0622(5) Uani 1 1 d . . . . .
C00F C 0.57988(8) 0.2996(4) 0.69395(9) 0.0658(5) Uani 1 1 d . . . . .
H00H H 0.551949 0.226033 0.705257 0.079 Uiso 1 1 calc R U . . .
H00I H 0.599194 0.197080 0.678139 0.079 Uiso 1 1 calc R U . . .
C00G C 0.55757(9) 0.4657(4) 0.65367(9) 0.0681(6) Uani 1 1 d . . . . .
H00J H 0.585061 0.526770 0.638986 0.082 Uiso 1 1 calc R U . . .
H00K H 0.532966 0.400402 0.625482 0.082 Uiso 1 1 calc R U . . .
C00H C 0.67776(8) 0.2907(4) 0.82065(9) 0.0659(6) Uani 1 1 d . . . . .
H00L H 0.664187 0.389932 0.843220 0.079 Uiso 1 1 calc R U . . .
C00I C 0.70655(8) 0.1066(4) 0.85281(10) 0.0681(6) Uani 1 1 d . . . . .
H00M H 0.700684 -0.028901 0.835372 0.082 Uiso 1 1 calc R U . . .
H00N H 0.700453 0.098124 0.888096 0.082 Uiso 1 1 calc R U . . .
C00J C 0.63671(8) 0.2243(4) 0.77579(10) 0.0693(6) Uani 1 1 d . . . . .
H00O H 0.650946 0.118406 0.755973 0.083 Uiso 1 1 calc R U . . .
H00P H 0.609150 0.158061 0.789381 0.083 Uiso 1 1 calc R U . . .
C00K C 0.43496(9) 0.7823(4) 0.56517(9) 0.0759(7) Uani 1 1 d . . . . .
C00L C 0.80610(13) 0.1182(5) 0.94170(10) 0.0922(9) Uani 1 1 d . . . . .
H00Q H 0.775644 0.043490 0.945843 0.138 Uiso 1 1 calc R U . . .
H00R H 0.823166 0.174974 0.974813 0.138 Uiso 1 1 calc R U . . .
H00S H 0.828980 0.023287 0.929012 0.138 Uiso 1 1 calc R U . . .
C00M C 0.75805(13) 0.4605(6) 0.92591(11) 0.1001(10) Uani 1 1 d . . . . .
H00T H 0.749173 0.576680 0.902203 0.150 Uiso 1 1 calc R U . . .
H00U H 0.777547 0.511382 0.958666 0.150 Uiso 1 1 calc R U . . .
H00V H 0.727079 0.393493 0.931425 0.150 Uiso 1 1 calc R U . . .
C00N C 0.88527(12) 0.3849(5) 0.91358(12) 0.0945(9) Uani 1 1 d . U . . .
H00W H 0.894209 0.278549 0.938288 0.113 Uiso 1 1 calc R U . . .
H00X H 0.910836 0.468235 0.904202 0.113 Uiso 1 1 calc R U . . .
C00O C 0.43376(16) 0.6560(6) 0.51485(13) 0.1153(12) Uani 1 1 d . . . . .
H00Y H 0.467974 0.648192 0.507968 0.173 Uiso 1 1 calc R U . . .
H H 0.411287 0.724582 0.486162 0.173 Uiso 1 1 calc R U . . .
HA H 0.421260 0.516063 0.518934 0.173 Uiso 1 1 calc R U . . .
C00P C 0.4491(2) 1.0046(6) 0.55632(15) 0.1392(17) Uani 1 1 d . . . . .
H00Z H 0.443135 1.090935 0.584663 0.209 Uiso 1 1 calc R U . . .
HB H 0.428350 1.054741 0.524097 0.209 Uiso 1 1 calc R U . . .
HC H 0.484920 1.011498 0.554485 0.209 Uiso 1 1 calc R U . . .
C00Q C 0.38592(12) 0.7509(11) 0.58314(17) 0.152(2) Uani 1 1 d . . . . .
H00 H 0.381155 0.603415 0.588990 0.229 Uiso 1 1 calc R U . . .
HD H 0.357658 0.801978 0.556961 0.229 Uiso 1 1 calc R U . . .
HE H 0.387161 0.827108 0.615116 0.229 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 H001 0.8200 . ?
O001 C007 1.308(2) . ?
O002 C00E 1.326(3) . ?
O002 C00K 1.467(3) . ?
N003 C00B 1.459(3) . ?
N003 C00F 1.473(3) . ?
N003 C00J 1.485(3) . ?
O004 C007 1.214(2) . ?
N005 C00C 1.453(3) . ?
N005 C00E 1.361(3) . ?
N005 C00G 1.462(3) . ?
O006 C00E 1.212(3) . ?
C007 C008 1.513(3) . ?
C008 C009 1.556(2) . ?
C008 C00D 1.568(3) . ?
C008 C00I 1.553(3) . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C009 C00H 1.553(3) . ?
C00A H00C 0.9300 . ?
C00A C00D 1.506(3) . ?
C00A C00N 1.295(4) . ?
C00B H00D 0.9700 . ?
C00B H00E 0.9700 . ?
C00B C00C 1.497(3) . ?
C00C H00F 0.9700 . ?
C00C H00G 0.9700 . ?
C00D C00L 1.537(3) . ?
C00D C00M 1.550(4) . ?
C00F H00H 0.9700 . ?
C00F H00I 0.9700 . ?
C00F C00G 1.520(3) . ?
C00G H00J 0.9700 . ?
C00G H00K 0.9700 . ?
C00H H00L 0.9800 . ?
C00H C00I 1.544(3) . ?
C00H C00J 1.486(3) . ?
C00I H00M 0.9700 . ?
C00I H00N 0.9700 . ?
C00J H00O 0.9700 . ?
C00J H00P 0.9700 . ?
C00K C00O 1.535(5) . ?
C00K C00P 1.488(5) . ?
C00K C00Q 1.482(5) . ?
C00L H00Q 0.9600 . ?
C00L H00R 0.9600 . ?
C00L H00S 0.9600 . ?
C00M H00T 0.9600 . ?
C00M H00U 0.9600 . ?
C00M H00V 0.9600 . ?
C00N H00W 0.9300 . ?
C00N H00X 0.9300 . ?
C00O H00Y 0.9600 . ?
C00O H 0.9600 . ?
C00O HA 0.9600 . ?
C00P H00Z 0.9600 . ?
C00P HB 0.9600 . ?
C00P HC 0.9600 . ?
C00Q H00 0.9600 . ?
C00Q HD 0.9600 . ?
C00Q HE 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
C007 O001 H001 109.5 . . ?
C00E O002 C00K 121.3(2) . . ?
C00B N003 C00F 108.19(15) . . ?
C00B N003 C00J 113.42(17) . . ?
C00F N003 C00J 108.19(17) . . ?
C00C N005 C00G 114.08(16) . . ?
C00E N005 C00C 118.03(18) . . ?
C00E N005 C00G 122.97(18) . . ?
O001 C007 C008 114.11(16) . . ?
O004 C007 O001 122.10(19) . . ?
O004 C007 C008 123.78(19) . . ?
C007 C008 C009 113.17(15) . . ?
C007 C008 C00D 109.22(15) . . ?
C007 C008 C00I 112.06(18) . . ?
C009 C008 C00D 116.96(17) . . ?
C00I C008 C009 88.88(14) . . ?
C00I C008 C00D 115.42(17) . . ?
C008 C009 H00A 113.7 . . ?
C008 C009 H00B 113.7 . . ?
H00A C009 H00B 110.9 . . ?
C00H C009 C008 89.94(14) . . ?
C00H C009 H00A 113.7 . . ?
C00H C009 H00B 113.7 . . ?
C00D C00A H00C 116.3 . . ?
C00N C00A H00C 116.3 . . ?
C00N C00A C00D 127.5(3) . . ?
N003 C00B H00D 109.4 . . ?
N003 C00B H00E 109.4 . . ?
N003 C00B C00C 111.20(17) . . ?
H00D C00B H00E 108.0 . . ?
C00C C00B H00D 109.4 . . ?
C00C C00B H00E 109.4 . . ?
N005 C00C C00B 110.73(19) . . ?
N005 C00C H00F 109.5 . . ?
N005 C00C H00G 109.5 . . ?
C00B C00C H00F 109.5 . . ?
C00B C00C H00G 109.5 . . ?
H00F C00C H00G 108.1 . . ?
C00A C00D C008 109.57(16) . . ?
C00A C00D C00L 112.2(2) . . ?
C00A C00D C00M 106.6(2) . . ?
C00L C00D C008 109.4(2) . . ?
C00L C00D C00M 108.6(2) . . ?
C00M C00D C008 110.49(18) . . ?
O002 C00E N005 111.3(2) . . ?
O006 C00E O002 125.1(2) . . ?
O006 C00E N005 123.6(2) . . ?
N003 C00F H00H 109.4 . . ?
N003 C00F H00I 109.4 . . ?
N003 C00F C00G 111.08(17) . . ?
H00H C00F H00I 108.0 . . ?
C00G C00F H00H 109.4 . . ?
C00G C00F H00I 109.4 . . ?
N005 C00G C00F 110.54(18) . . ?
N005 C00G H00J 109.5 . . ?
N005 C00G H00K 109.5 . . ?
C00F C00G H00J 109.5 . . ?
C00F C00G H00K 109.5 . . ?
H00J C00G H00K 108.1 . . ?
C009 C00H H00L 111.0 . . ?
C00I C00H C009 89.28(15) . . ?
C00I C00H H00L 111.0 . . ?
C00J C00H C009 118.47(19) . . ?
C00J C00H H00L 111.0 . . ?
C00J C00H C00I 114.5(2) . . ?
C008 C00I H00M 113.6 . . ?
C008 C00I H00N 113.6 . . ?
C00H C00I C008 90.38(15) . . ?
C00H C00I H00M 113.6 . . ?
C00H C00I H00N 113.6 . . ?
H00M C00I H00N 110.8 . . ?
N003 C00J C00H 115.39(19) . . ?
N003 C00J H00O 108.4 . . ?
N003 C00J H00P 108.4 . . ?
C00H C00J H00O 108.4 . . ?
C00H C00J H00P 108.4 . . ?
H00O C00J H00P 107.5 . . ?
O002 C00K C00O 102.1(2) . . ?
O002 C00K C00P 110.0(2) . . ?
O002 C00K C00Q 109.2(2) . . ?
C00P C00K C00O 108.8(3) . . ?
C00Q C00K C00O 109.7(3) . . ?
C00Q C00K C00P 116.2(4) . . ?
C00D C00L H00Q 109.5 . . ?
C00D C00L H00R 109.5 . . ?
C00D C00L H00S 109.5 . . ?
H00Q C00L H00R 109.5 . . ?
H00Q C00L H00S 109.5 . . ?
H00R C00L H00S 109.5 . . ?
C00D C00M H00T 109.5 . . ?
C00D C00M H00U 109.5 . . ?
C00D C00M H00V 109.5 . . ?
H00T C00M H00U 109.5 . . ?
H00T C00M H00V 109.5 . . ?
H00U C00M H00V 109.5 . . ?
C00A C00N H00W 120.0 . . ?
C00A C00N H00X 120.0 . . ?
H00W C00N H00X 120.0 . . ?
C00K C00O H00Y 109.5 . . ?
C00K C00O H 109.5 . . ?
C00K C00O HA 109.5 . . ?
H00Y C00O H 109.5 . . ?
H00Y C00O HA 109.5 . . ?
H C00O HA 109.5 . . ?
C00K C00P H00Z 109.5 . . ?
C00K C00P HB 109.5 . . ?
C00K C00P HC 109.5 . . ?
H00Z C00P HB 109.5 . . ?
H00Z C00P HC 109.5 . . ?
HB C00P HC 109.5 . . ?
C00K C00Q H00 109.5 . . ?
C00K C00Q HD 109.5 . . ?
C00K C00Q HE 109.5 . . ?
H00 C00Q HD 109.5 . . ?
H00 C00Q HE 109.5 . . ?
HD C00Q HE 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
O001 C007 C008 C009 41.1(2) . . . . ?
O001 C007 C008 C00D -91.12(19) . . . . ?
O001 C007 C008 C00I 139.70(17) . . . . ?
N003 C00B C00C N005 57.3(2) . . . . ?
N003 C00F C00G N005 -54.4(2) . . . . ?
O004 C007 C008 C009 -137.8(2) . . . . ?
O004 C007 C008 C00D 90.0(2) . . . . ?
O004 C007 C008 C00I -39.2(3) . . . . ?
C007 C008 C009 C00H 122.86(18) . . . . ?
C007 C008 C00D C00A 60.2(2) . . . . ?
C007 C008 C00D C00L -63.2(2) . . . . ?
C007 C008 C00D C00M 177.4(2) . . . . ?
C007 C008 C00I C00H -123.95(17) . . . . ?
C008 C009 C00H C00I -9.32(18) . . . . ?
C008 C009 C00H C00J -127.0(2) . . . . ?
C009 C008 C00D C00A -69.9(2) . . . . ?
C009 C008 C00D C00L 166.68(19) . . . . ?
C009 C008 C00D C00M 47.2(3) . . . . ?
C009 C008 C00I C00H -9.33(18) . . . . ?
C009 C00H C00I C008 9.34(17) . . . . ?
C009 C00H C00J N003 -67.6(3) . . . . ?
C00B N003 C00F C00G 59.8(2) . . . . ?
C00B N003 C00J C00H -67.9(2) . . . . ?
C00C N005 C00E O002 164.24(19) . . . . ?
C00C N005 C00E O006 -16.2(3) . . . . ?
C00C N005 C00G C00F 50.5(3) . . . . ?
C00D C008 C009 C00H -108.87(18) . . . . ?
C00D C008 C00I C00H 110.19(19) . . . . ?
C00E O002 C00K C00O 174.6(2) . . . . ?
C00E O002 C00K C00P 59.2(4) . . . . ?
C00E O002 C00K C00Q -69.3(4) . . . . ?
C00E N005 C00C C00B 152.22(19) . . . . ?
C00E N005 C00G C00F -154.9(2) . . . . ?
C00F N003 C00B C00C -61.3(2) . . . . ?
C00F N003 C00J C00H 172.07(19) . . . . ?
C00G N005 C00C C00B -51.8(3) . . . . ?
C00G N005 C00E O002 10.6(3) . . . . ?
C00G N005 C00E O006 -169.9(2) . . . . ?
C00I C008 C009 C00H 9.27(18) . . . . ?
C00I C008 C00D C00A -172.48(17) . . . . ?
C00I C008 C00D C00L 64.1(2) . . . . ?
C00I C008 C00D C00M -55.3(3) . . . . ?
C00I C00H C00J N003 -170.93(18) . . . . ?
C00J N003 C00B C00C 178.64(17) . . . . ?
C00J N003 C00F C00G -176.90(18) . . . . ?
C00J C00H C00I C008 130.5(2) . . . . ?
C00K O002 C00E N005 178.76(19) . . . . ?
C00K O002 C00E O006 -0.8(4) . . . . ?
C00N C00A C00D C008 -123.9(3) . . . . ?
C00N C00A C00D C00L -2.2(4) . . . . ?
C00N C00A C00D C00M 116.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.848
####################################################################### 
# 
# 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_zfq-2-20240708_auto
_database_code_depnum_ccdc_archive 'CCDC 2403839'
loop_
_audit_author_name
_audit_author_address
'Zhang Fangqing'
;Peking University
China
;
_audit_update_record             
;
2024-11-19 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_audit_creation_date             2024-07-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H24 N2 O2'
_chemical_formula_sum            'C19 H24 N2 O2'
_chemical_formula_weight         312.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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                   9.7265(2)
_cell_length_b                   14.7461(2)
_cell_length_c                   12.5014(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.624(2)
_cell_angle_gamma                90
_cell_volume                     1699.16(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8141
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.6770
_cell_measurement_theta_min      4.7720
_shelx_estimated_absorpt_T_max   0.884
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (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    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10262
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.910
_diffrn_reflns_theta_min         4.788
_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 0.998
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     74.00 100.00   0.50    0.11    --  105.65 -94.00  90.00   52
  2  ω     36.00  62.00   0.50    0.11    --  105.65 -94.00  90.00   52
  3  ω    -21.00  28.00   0.50    0.05    --   46.79 -94.00-108.00   98
  4  ω     31.00  57.00   0.50    0.05    --   46.79 -94.00-108.00   52
  5  ω     33.00 104.00   0.50    0.11    --  105.65 -94.00-108.00  142
  6  ω     33.00  58.00   0.50    0.11    --  105.65 -61.00 -90.00   50
  7  ω     33.00  58.00   0.50    0.11    --  105.65 -61.00 -60.00   50
  8  ω    -27.00  -1.00   0.50    0.05    --   46.79 -19.00-180.00   52
  9  ω    -15.00  28.00   0.50    0.05    --   46.79 -19.00-120.00   86
 10  ω    118.00 144.00   0.50    0.11    --  105.65  94.00   3.00   52
 11  ω    131.00 157.00   0.50    0.11    --  105.65  61.00 -30.00   52
 12  ω    100.00 126.00   0.50    0.11    --  105.65  61.00 -30.00   52
 13  ω    -64.00 -33.00   0.50    0.11    -- -104.00  61.00-180.00   62
 14  ω    -57.00 -31.00   0.50    0.11    -- -104.00  61.00-150.00   52
 15  ω    -68.00 -36.00   0.50    0.11    -- -104.00  61.00 -30.00   64
 16  ω    -68.00 -34.00   0.50    0.11    -- -104.00  61.00 120.00   68
 17  ω    -65.00 -34.00   0.50    0.11    -- -104.00  61.00 150.00   62
 18  ω    -38.00  26.00   0.50    0.05    --  -46.79  37.00 120.00  128
 19  ω    -62.00  25.00   0.50    0.05    --  -46.79  94.00   3.00  174
 20  ω   -101.00 -37.00   0.50    0.11    -- -104.00  94.00   3.00  128
 21  ω   -174.00 -96.00   0.50    0.11    -- -104.00 -45.00 -90.00  156
 22  ω   -149.00-116.00   0.50    0.11    -- -104.00 -94.00-108.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1352807000
_diffrn_orient_matrix_UB_12      0.0585990000
_diffrn_orient_matrix_UB_13      0.0549517000
_diffrn_orient_matrix_UB_21      0.0658712000
_diffrn_orient_matrix_UB_22      -0.0770490000
_diffrn_orient_matrix_UB_23      0.0839784000
_diffrn_orient_matrix_UB_31      0.0727664000
_diffrn_orient_matrix_UB_32      -0.0392616000
_diffrn_orient_matrix_UB_33      -0.0827351000
_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                3100
_reflns_number_total             3388
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.033
_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)+(0.0466P)²+0.5207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0979
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 C19, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C19 \\sim C22 \\sim C23 \\sim C22A \\sim C23A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Same fragment restrains
{C19, C22A, C23A} sigma for 1-2: 0.01, 1-3: 0.02
as in
{C19, C22, C23}
5. Others
 Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23A)=1-FVAR(1)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23)=FVAR(1)
 Sof(H18)=1-FVAR(2)
 Sof(H17)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C12(H12)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C23(H23), C23A(H23A)
6.d X=CH2 refined with riding coordinates:
 C22(H22A,H22B), C22A(H22C,H22D)
6.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
6.f Idealised tetrahedral OH refined as rotating group:
 O17(H17), O18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.85115(11) 0.80327(7) 0.49428(9) 0.0219(2) Uani 1 1 d . . . . .
C2 C 0.91087(11) 0.79815(8) 0.61308(9) 0.0233(2) Uani 1 1 d . . . . .
H2 H 0.9261 0.8522 0.6567 0.028 Uiso 1 1 calc R U . . .
C3 C 0.94734(11) 0.71544(8) 0.66631(9) 0.0238(2) Uani 1 1 d . . . . .
H3 H 0.9874 0.7134 0.7462 0.029 Uiso 1 1 calc R U . . .
C4 C 0.92633(11) 0.63474(8) 0.60472(9) 0.0229(2) Uani 1 1 d . . . . .
C5 C 0.87163(11) 0.63916(7) 0.48688(9) 0.0226(2) Uani 1 1 d . . . . .
H5 H 0.8595 0.5850 0.4437 0.027 Uiso 1 1 calc R U . . .
C6 C 0.83528(12) 0.72129(8) 0.43303(9) 0.0232(2) Uani 1 1 d . . . . .
H6 H 0.7987 0.7229 0.3529 0.028 Uiso 1 1 calc R U . . .
C8 C 0.81638(15) 0.96652(8) 0.50802(12) 0.0356(3) Uani 1 1 d . . . . .
H8A H 0.7492 0.9597 0.5515 0.053 Uiso 1 1 calc R U . . .
H8B H 0.7880 1.0192 0.4581 0.053 Uiso 1 1 calc R U . . .
H8C H 0.9151 0.9753 0.5598 0.053 Uiso 1 1 calc R U . . .
C9 C 0.71714(13) 0.88791(8) 0.32295(10) 0.0273(3) Uani 1 1 d . . . . .
H9A H 0.7549 0.8454 0.2776 0.033 Uiso 1 1 calc R U . . .
H9B H 0.7188 0.9497 0.2924 0.033 Uiso 1 1 calc R U . . .
C10 C 0.95484(13) 0.54842(8) 0.66021(10) 0.0289(3) Uani 1 1 d . . . . .
C12 C 0.56134(12) 0.86239(8) 0.31144(9) 0.0240(2) Uani 1 1 d . . . . .
H12 H 0.5630 0.8059 0.3560 0.029 Uiso 1 1 calc R U . . .
C13 C 0.43848(12) 0.85248(8) 0.19400(9) 0.0239(2) Uani 1 1 d . . . . .
C14 C 0.33261(13) 0.89491(8) 0.25060(10) 0.0268(3) Uani 1 1 d . . . . .
H14A H 0.2684 0.9422 0.2044 0.032 Uiso 1 1 calc R U . . .
H14B H 0.2761 0.8496 0.2775 0.032 Uiso 1 1 calc R U . . .
C15 C 0.46412(13) 0.93297(8) 0.34442(9) 0.0268(3) Uani 1 1 d . . . . .
H15A H 0.4583 0.9245 0.4214 0.032 Uiso 1 1 calc R U . . .
H15B H 0.4877 0.9966 0.3320 0.032 Uiso 1 1 calc R U . . .
C16 C 0.46368(12) 0.91759(8) 0.10759(9) 0.0247(2) Uani 1 1 d . . . . .
C19 C 0.40255(14) 0.75518(8) 0.14120(9) 0.0291(3) Uani 1 1 d D U . . .
C22 C 0.4085(3) 0.63655(13) 0.28991(16) 0.0323(6) Uani 0.645(4) 1 d D U P A 1
H22A H 0.5085 0.6264 0.3007 0.039 Uiso 0.645(4) 1 calc R U P A 1
H22B H 0.3609 0.6032 0.3328 0.039 Uiso 0.645(4) 1 calc R U P A 1
C23 C 0.3359(3) 0.69701(14) 0.21551(17) 0.0264(5) Uani 0.645(4) 1 d D U P A 1
H23 H 0.2361 0.7055 0.2069 0.032 Uiso 0.645(4) 1 calc R U P A 1
C20 C 0.27199(14) 0.76040(10) 0.03308(12) 0.0396(3) Uani 1 1 d . U . . .
H20A H 0.1914 0.7910 0.0492 0.059 Uiso 1 1 calc R U . . .
H20B H 0.2422 0.6990 0.0054 0.059 Uiso 1 1 calc R U . . .
H20C H 0.2989 0.7945 -0.0245 0.059 Uiso 1 1 calc R U . . .
C21 C 0.53108(15) 0.71412(10) 0.11389(12) 0.0399(3) Uani 1 1 d . . . . .
H21A H 0.5510 0.7497 0.0543 0.060 Uiso 1 1 calc R U . . .
H21B H 0.5083 0.6515 0.0881 0.060 Uiso 1 1 calc R U . . .
H21C H 0.6166 0.7147 0.1817 0.060 Uiso 1 1 calc R U . . .
N7 N 0.81177(11) 0.88530(7) 0.44064(8) 0.0277(2) Uani 1 1 d . . . . .
N11 N 0.97631(14) 0.47915(8) 0.70442(10) 0.0418(3) Uani 1 1 d . . . . .
O17 O 0.58092(10) 0.91035(7) 0.08429(8) 0.0405(3) Uani 1 1 d . . . . .
H17 H 0.5792 0.9461 0.0315 0.061 Uiso 0.56(3) 1 calc R U P B 1
O18 O 0.36733(10) 0.97502(6) 0.06085(7) 0.0351(2) Uani 1 1 d . . . . .
H18 H 0.3933 1.0049 0.0134 0.053 Uiso 0.44(3) 1 calc R U P B 2
C22A C 0.3025(4) 0.6465(2) 0.2497(3) 0.0298(10) Uani 0.355(4) 1 d D U P A 2
H22C H 0.2095 0.6563 0.1959 0.036 Uiso 0.355(4) 1 calc R U P A 2
H22D H 0.3132 0.6060 0.3110 0.036 Uiso 0.355(4) 1 calc R U P A 2
C23A C 0.4160(5) 0.6890(2) 0.2395(3) 0.0237(9) Uani 0.355(4) 1 d D U P A 2
H23A H 0.5085 0.6788 0.2938 0.028 Uiso 0.355(4) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.4135(15) . ?
C1 C6 1.4127(15) . ?
C1 N7 1.3768(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.3803(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3966(16) . ?
C4 C5 1.3990(15) . ?
C4 C10 1.4336(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3759(15) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 N7 1.4567(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C12 1.5230(17) . ?
C9 N7 1.4658(15) . ?
C10 N11 1.1485(17) . ?
C12 H12 1.0000 . ?
C12 C13 1.5762(15) . ?
C12 C15 1.5481(15) . ?
C13 C14 1.5549(15) . ?
C13 C16 1.5226(15) . ?
C13 C19 1.5713(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5390(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O17 1.2684(14) . ?
C16 O18 1.2597(14) . ?
C19 C23 1.551(2) . ?
C19 C20 1.5327(18) . ?
C19 C21 1.5227(18) . ?
C19 C23A 1.542(3) . ?
C22 H22A 0.9500 . ?
C22 H22B 0.9500 . ?
C22 C23 1.319(3) . ?
C23 H23 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O17 H17 0.8400 . ?
O18 H18 0.8400 . ?
C22A H22C 0.9500 . ?
C22A H22D 0.9500 . ?
C22A C23A 1.310(5) . ?
C23A H23A 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
C6 C1 C2 117.44(10) . . ?
N7 C1 C2 121.05(10) . . ?
N7 C1 C6 121.51(10) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.65(10) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.15(10) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.71(10) . . ?
C3 C4 C10 121.21(10) . . ?
C5 C4 C10 120.04(10) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.54(10) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.44(10) . . ?
C5 C6 H6 119.3 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N7 C8 H8A 109.5 . . ?
N7 C8 H8B 109.5 . . ?
N7 C8 H8C 109.5 . . ?
H9A C9 H9B 107.9 . . ?
C12 C9 H9A 109.2 . . ?
C12 C9 H9B 109.2 . . ?
N7 C9 H9A 109.2 . . ?
N7 C9 H9B 109.2 . . ?
N7 C9 C12 112.04(9) . . ?
N11 C10 C4 179.36(13) . . ?
C9 C12 H12 108.3 . . ?
C9 C12 C13 123.12(9) . . ?
C9 C12 C15 118.86(10) . . ?
C13 C12 H12 108.3 . . ?
C15 C12 H12 108.3 . . ?
C15 C12 C13 87.96(8) . . ?
C14 C13 C12 87.37(8) . . ?
C14 C13 C19 117.89(10) . . ?
C16 C13 C12 110.88(9) . . ?
C16 C13 C14 110.43(9) . . ?
C16 C13 C19 110.02(9) . . ?
C19 C13 C12 118.47(9) . . ?
C13 C14 H14A 113.8 . . ?
C13 C14 H14B 113.8 . . ?
H14A C14 H14B 111.0 . . ?
C15 C14 C13 89.06(8) . . ?
C15 C14 H14A 113.8 . . ?
C15 C14 H14B 113.8 . . ?
C12 C15 H15A 113.8 . . ?
C12 C15 H15B 113.8 . . ?
C14 C15 C12 88.94(9) . . ?
C14 C15 H15A 113.8 . . ?
C14 C15 H15B 113.8 . . ?
H15A C15 H15B 111.0 . . ?
O17 C16 C13 118.04(10) . . ?
O18 C16 C13 119.24(10) . . ?
O18 C16 O17 122.70(10) . . ?
C23 C19 C13 109.45(10) . . ?
C20 C19 C13 109.58(10) . . ?
C20 C19 C23 99.72(14) . . ?
C20 C19 C23A 124.8(2) . . ?
C21 C19 C13 111.65(10) . . ?
C21 C19 C23 116.41(13) . . ?
C21 C19 C20 109.31(10) . . ?
C21 C19 C23A 93.44(18) . . ?
C23A C19 C13 107.00(15) . . ?
H22A C22 H22B 120.0 . . ?
C23 C22 H22A 120.0 . . ?
C23 C22 H22B 120.0 . . ?
C19 C23 H23 117.8 . . ?
C22 C23 C19 124.3(2) . . ?
C22 C23 H23 117.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N7 C8 119.23(10) . . ?
C1 N7 C9 119.99(9) . . ?
C8 N7 C9 116.89(9) . . ?
C16 O17 H17 109.5 . . ?
C16 O18 H18 109.5 . . ?
H22C C22A H22D 120.0 . . ?
C23A C22A H22C 120.0 . . ?
C23A C22A H22D 120.0 . . ?
C19 C23A H23A 119.3 . . ?
C22A C23A C19 121.4(4) . . ?
C22A C23A H23A 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.06(16) . . . . ?
C2 C1 C6 C5 2.25(16) . . . . ?
C2 C1 N7 C8 -7.05(16) . . . . ?
C2 C1 N7 C9 -164.18(10) . . . . ?
C2 C3 C4 C5 2.07(16) . . . . ?
C2 C3 C4 C10 -175.70(10) . . . . ?
C3 C4 C5 C6 -1.90(16) . . . . ?
C4 C5 C6 C1 -0.28(16) . . . . ?
C6 C1 C2 C3 -2.07(15) . . . . ?
C6 C1 N7 C8 173.75(11) . . . . ?
C6 C1 N7 C9 16.62(15) . . . . ?
C9 C12 C13 C14 -142.77(11) . . . . ?
C9 C12 C13 C16 -31.89(14) . . . . ?
C9 C12 C13 C19 96.71(12) . . . . ?
C9 C12 C15 C14 146.56(10) . . . . ?
C10 C4 C5 C6 175.90(10) . . . . ?
C12 C9 N7 C1 72.23(13) . . . . ?
C12 C9 N7 C8 -85.42(13) . . . . ?
C12 C13 C14 C15 19.27(8) . . . . ?
C12 C13 C16 O17 59.73(14) . . . . ?
C12 C13 C16 O18 -121.50(12) . . . . ?
C12 C13 C19 C23 66.71(16) . . . . ?
C12 C13 C19 C20 175.11(10) . . . . ?
C12 C13 C19 C21 -63.64(12) . . . . ?
C12 C13 C19 C23A 37.2(2) . . . . ?
C13 C12 C15 C14 19.35(8) . . . . ?
C13 C14 C15 C12 -19.62(8) . . . . ?
C13 C19 C23 C22 -100.1(2) . . . . ?
C13 C19 C23A C22A 113.4(3) . . . . ?
C14 C13 C16 O17 154.88(11) . . . . ?
C14 C13 C16 O18 -26.35(15) . . . . ?
C14 C13 C19 C23 -36.47(16) . . . . ?
C14 C13 C19 C20 71.93(12) . . . . ?
C14 C13 C19 C21 -166.82(10) . . . . ?
C14 C13 C19 C23A -65.9(2) . . . . ?
C15 C12 C13 C14 -19.16(8) . . . . ?
C15 C12 C13 C16 91.72(10) . . . . ?
C15 C12 C13 C19 -139.68(10) . . . . ?
C16 C13 C14 C15 -92.06(10) . . . . ?
C16 C13 C19 C23 -164.29(14) . . . . ?
C16 C13 C19 C20 -55.90(12) . . . . ?
C16 C13 C19 C21 65.35(12) . . . . ?
C16 C13 C19 C23A 166.2(2) . . . . ?
C19 C13 C14 C15 140.31(10) . . . . ?
C19 C13 C16 O17 -73.28(14) . . . . ?
C19 C13 C16 O18 105.49(12) . . . . ?
C20 C19 C23 C22 145.04(19) . . . . ?
C20 C19 C23A C22A -16.3(4) . . . . ?
C21 C19 C23 C22 27.7(2) . . . . ?
C21 C19 C23A C22A -132.7(3) . . . . ?
N7 C1 C2 C3 178.69(10) . . . . ?
N7 C1 C6 C5 -178.52(10) . . . . ?
N7 C9 C12 C13 -175.38(9) . . . . ?
N7 C9 C12 C15 76.49(12) . . . . ?

_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 1.071
_oxdiff_exptl_absorpt_empirical_full_min 0.922
