# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_yangyh_0908
_database_code_depnum_ccdc_archive 'CCDC 2086809'
loop_
_audit_author_name
_audit_author_address
'Tao Shi'
;Lanzhou University
China
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2022-05-22 downloaded from the CCDC.
;
_audit_creation_date             2020-09-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        (E)-bisdehydroneostemonine
_chemical_formula_moiety         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.8432(4)
_cell_length_b                   8.2643(4)
_cell_length_c                   24.8497(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1610.72(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3331
_cell_measurement_temperature    292.5(2)
_cell_measurement_theta_max      69.4920
_cell_measurement_theta_min      7.1200
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8319
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.987
_diffrn_reflns_theta_min         3.557
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.5(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    150.00 178.00   1.00    2.00    --  108.00  38.00 -60.00   28
  2  ω     63.00 101.00   1.00    1.00    --   54.00-125.00 120.00   38
  3  ω     51.00 130.00   1.00    2.00    --  108.00 -63.00 120.00   79
  4  ω     40.00 115.00   1.00    2.00    --  108.00-111.00 120.00   75
  5  ω     37.00 138.00   1.00    2.00    --  108.00 -25.00 120.00  101
  6  ω     48.00  73.00   1.00    1.00    --    0.00  19.00  90.00   25
  7  ω     30.00 123.00   1.00    1.00    --   54.00  38.00 150.00   93
  8  ω      3.00  36.00   1.00    1.00    --    0.00  19.00  90.00   33
  9  ω    -37.00 -10.00   1.00    1.00    --    0.00  19.00  90.00   27
 10  ω     48.00  74.00   1.00    1.00    --   54.00 -57.00-180.00   26
 11  ω     -2.00  27.00   1.00    1.00    --   54.00 -57.00-180.00   29
 12  ω    -51.00 -25.00   1.00    1.00    --    0.00 131.00 -60.00   26
 13  ω     30.00  82.00   1.00    1.00    --   54.00-125.00-150.00   52
 14  ω     39.00  76.00   1.00    1.00    --   54.00  57.00 -90.00   37
 15  ω     67.00  99.00   1.00    2.00    --  108.00 178.00   0.00   32
 16  ω    101.00 127.00   1.00    2.00    --  108.00 111.00  90.00   26
 17  ω    150.00 176.00   1.00    2.00    --  108.00 111.00  90.00   26
 18  ω    152.00 178.00   1.00    2.00    --  108.00 111.00 120.00   26
 19  ω    117.00 143.00   1.00    2.00    --  108.00 111.00 120.00   26
 20  ω    105.00 147.00   1.00    2.00    --  108.00 178.00   0.00   42
 21  ω    121.00 175.00   1.00    2.00    --  108.00  63.00  90.00   54
 22  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00 150.00   90
 23  ω    -44.00  73.00   1.00    1.00    --    0.00  19.00 -60.00  117
 24  ω     24.00 124.00   1.00    1.00    --   54.00  77.00  30.00  100
 25  ω     24.00 124.00   1.00    1.00    --   54.00  77.00-180.00  100
 26  ω    -18.00  32.00   1.00    1.00    --   54.00 -38.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0194775000
_diffrn_orient_matrix_UB_12      0.0205338000
_diffrn_orient_matrix_UB_13      0.0612794000
_diffrn_orient_matrix_UB_21      0.1954101000
_diffrn_orient_matrix_UB_22      -0.0074717000
_diffrn_orient_matrix_UB_23      -0.0058923000
_diffrn_orient_matrix_UB_31      0.0058181000
_diffrn_orient_matrix_UB_32      0.1851881000
_diffrn_orient_matrix_UB_33      -0.0070200000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2684
_reflns_number_total             2983
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 965 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.041
_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)+(0.0503P)²+0.0370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5876(2) 0.6360(2) 0.75457(6) 0.0534(5) Uani 1 1 d . . . . .
O2 O 0.3032(2) 0.5938(2) 0.64154(6) 0.0469(4) Uani 1 1 d . . . . .
O3 O 0.2400(3) 0.5683(2) 0.55409(7) 0.0639(6) Uani 1 1 d . . . . .
O4 O 0.7460(3) 0.6596(2) 0.65368(7) 0.0565(5) Uani 1 1 d . . . . .
N1 N 0.3259(3) 0.6258(3) 0.91370(7) 0.0474(5) Uani 1 1 d . . . . .
C1 C 0.2678(3) 0.6540(3) 0.86246(9) 0.0401(5) Uani 1 1 d . . . . .
C2 C 0.3655(3) 0.5907(3) 0.81540(9) 0.0381(5) Uani 1 1 d . . . . .
H2 H 0.377435 0.473364 0.819624 0.046 Uiso 1 1 calc R U . . .
C3 C 0.5421(3) 0.6630(3) 0.81070(9) 0.0431(6) Uani 1 1 d . . . . .
H3 H 0.536164 0.779562 0.817688 0.052 Uiso 1 1 calc R U . . .
C4 C 0.6759(4) 0.5884(4) 0.84635(11) 0.0570(7) Uani 1 1 d . . . . .
H4A H 0.786634 0.631663 0.836597 0.068 Uiso 1 1 calc R U . . .
H4B H 0.678543 0.472485 0.840171 0.068 Uiso 1 1 calc R U . . .
C5 C 0.6441(4) 0.6199(4) 0.90601(11) 0.0595(7) Uani 1 1 d . . . . .
H5A H 0.741015 0.579926 0.926281 0.071 Uiso 1 1 calc R U . . .
H5B H 0.637809 0.735907 0.911666 0.071 Uiso 1 1 calc R U . . .
C6 C 0.4830(4) 0.5429(3) 0.92845(11) 0.0553(7) Uani 1 1 d . . . . .
H6A H 0.476611 0.431996 0.915846 0.066 Uiso 1 1 calc R U . . .
H6B H 0.491340 0.540026 0.967383 0.066 Uiso 1 1 calc R U . . .
C7 C 0.2147(4) 0.6968(3) 0.94911(11) 0.0587(8) Uani 1 1 d . . . . .
H7 H 0.224956 0.695521 0.986390 0.070 Uiso 1 1 calc R U . . .
C8 C 0.0873(4) 0.7693(4) 0.92117(11) 0.0620(8) Uani 1 1 d . . . . .
H8 H -0.004599 0.825897 0.935502 0.074 Uiso 1 1 calc R U . . .
C9 C 0.1212(4) 0.7424(3) 0.86615(10) 0.0512(6) Uani 1 1 d . . . . .
H9 H 0.055311 0.778404 0.837436 0.061 Uiso 1 1 calc R U . . .
C10 C 0.2858(3) 0.6239(3) 0.76021(9) 0.0411(5) Uani 1 1 d . . . . .
H10 H 0.238309 0.733551 0.760459 0.049 Uiso 1 1 calc R U . . .
C11 C 0.4431(3) 0.6236(3) 0.72496(10) 0.0405(5) Uani 1 1 d . . . . .
C12 C 0.1434(4) 0.5057(4) 0.74582(10) 0.0585(8) Uani 1 1 d . . . . .
H12A H 0.188663 0.397875 0.744124 0.088 Uiso 1 1 calc R U . . .
H12B H 0.096005 0.534359 0.711500 0.088 Uiso 1 1 calc R U . . .
H12C H 0.055873 0.510447 0.772788 0.088 Uiso 1 1 calc R U . . .
C13 C 0.4528(3) 0.6162(3) 0.67145(9) 0.0412(5) Uani 1 1 d . . . . .
C14 C 0.5923(3) 0.6270(3) 0.63337(10) 0.0419(5) Uani 1 1 d . . . . .
C15 C 0.5307(3) 0.6080(3) 0.58270(9) 0.0442(6) Uani 1 1 d . . . . .
C16 C 0.3492(4) 0.5880(3) 0.58782(9) 0.0467(6) Uani 1 1 d . . . . .
C17 C 0.8799(4) 0.7064(4) 0.61759(12) 0.0708(9) Uani 1 1 d . . . . .
H17A H 0.910360 0.616009 0.595311 0.106 Uiso 1 1 calc R U . . .
H17B H 0.977525 0.740401 0.637962 0.106 Uiso 1 1 calc R U . . .
H17C H 0.841415 0.794059 0.595349 0.106 Uiso 1 1 calc R U . . .
C18 C 0.6103(4) 0.6069(4) 0.52782(10) 0.0637(8) Uani 1 1 d . . . . .
H18A H 0.535501 0.553239 0.502986 0.096 Uiso 1 1 calc R U . . .
H18B H 0.717234 0.550575 0.529234 0.096 Uiso 1 1 calc R U . . .
H18C H 0.629031 0.716166 0.516117 0.096 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 C3 1.457(3) . ?
O1 C11 1.356(3) . ?
O2 C13 1.401(3) . ?
O2 C16 1.383(3) . ?
O3 C16 1.210(3) . ?
O4 C14 1.335(3) . ?
O4 C17 1.434(3) . ?
N1 C1 1.372(3) . ?
N1 C6 1.456(4) . ?
N1 C7 1.371(3) . ?
C1 C2 1.493(3) . ?
C1 C9 1.365(4) . ?
C2 H2 0.9800 . ?
C2 C3 1.512(3) . ?
C2 C10 1.532(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.506(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.526(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.521(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C8 1.356(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.411(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9800 . ?
C10 C11 1.513(3) . ?
C10 C12 1.527(3) . ?
C11 C13 1.333(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.449(3) . ?
C14 C15 1.358(3) . ?
C15 C16 1.439(4) . ?
C15 C18 1.500(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C3 109.03(18) . . ?
C16 O2 C13 107.4(2) . . ?
C14 O4 C17 118.6(2) . . ?
C1 N1 C6 126.5(2) . . ?
C7 N1 C1 108.1(2) . . ?
C7 N1 C6 125.3(2) . . ?
N1 C1 C2 119.8(2) . . ?
C9 C1 N1 108.0(2) . . ?
C9 C1 C2 132.2(2) . . ?
C1 C2 H2 108.2 . . ?
C1 C2 C3 113.09(19) . . ?
C1 C2 C10 115.4(2) . . ?
C3 C2 H2 108.2 . . ?
C3 C2 C10 103.52(18) . . ?
C10 C2 H2 108.2 . . ?
O1 C3 C2 103.78(18) . . ?
O1 C3 H3 109.4 . . ?
O1 C3 C4 109.2(2) . . ?
C2 C3 H3 109.4 . . ?
C4 C3 C2 115.5(2) . . ?
C4 C3 H3 109.4 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C3 C4 C5 112.8(2) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C4 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 C4 114.9(2) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
N1 C6 C5 114.4(2) . . ?
N1 C6 H6A 108.7 . . ?
N1 C6 H6B 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
N1 C7 H7 125.4 . . ?
C8 C7 N1 109.2(2) . . ?
C8 C7 H7 125.4 . . ?
C7 C8 H8 126.6 . . ?
C7 C8 C9 106.7(3) . . ?
C9 C8 H8 126.6 . . ?
C1 C9 C8 108.0(3) . . ?
C1 C9 H9 126.0 . . ?
C8 C9 H9 126.0 . . ?
C2 C10 H10 108.4 . . ?
C11 C10 C2 100.69(18) . . ?
C11 C10 H10 108.4 . . ?
C11 C10 C12 117.4(2) . . ?
C12 C10 C2 113.2(2) . . ?
C12 C10 H10 108.4 . . ?
O1 C11 C10 111.56(19) . . ?
C13 C11 O1 119.8(2) . . ?
C13 C11 C10 128.6(2) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C14 107.09(19) . . ?
C11 C13 O2 119.2(2) . . ?
C11 C13 C14 133.7(3) . . ?
O4 C14 C13 116.6(2) . . ?
O4 C14 C15 134.1(2) . . ?
C15 C14 C13 109.3(2) . . ?
C14 C15 C16 106.4(2) . . ?
C14 C15 C18 134.1(3) . . ?
C16 C15 C18 119.4(2) . . ?
O2 C16 C15 109.8(2) . . ?
O3 C16 O2 119.3(3) . . ?
O3 C16 C15 130.9(2) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 C5 176.4(2) . . . . ?
O1 C11 C13 O2 176.3(2) . . . . ?
O1 C11 C13 C14 -3.9(4) . . . . ?
O2 C13 C14 O4 175.6(2) . . . . ?
O2 C13 C14 C15 -1.4(3) . . . . ?
O4 C14 C15 C16 -175.1(3) . . . . ?
O4 C14 C15 C18 3.8(5) . . . . ?
N1 C1 C2 C3 -63.2(3) . . . . ?
N1 C1 C2 C10 177.9(2) . . . . ?
N1 C1 C9 C8 -0.1(3) . . . . ?
N1 C7 C8 C9 -0.1(3) . . . . ?
C1 N1 C6 C5 58.6(3) . . . . ?
C1 N1 C7 C8 0.0(3) . . . . ?
C1 C2 C3 O1 -159.4(2) . . . . ?
C1 C2 C3 C4 81.1(3) . . . . ?
C1 C2 C10 C11 153.34(19) . . . . ?
C1 C2 C10 C12 -80.5(3) . . . . ?
C2 C1 C9 C8 -179.6(2) . . . . ?
C2 C3 C4 C5 -67.1(3) . . . . ?
C2 C10 C11 O1 -15.2(3) . . . . ?
C2 C10 C11 C13 166.2(3) . . . . ?
C3 O1 C11 C10 -6.0(3) . . . . ?
C3 O1 C11 C13 172.7(2) . . . . ?
C3 C2 C10 C11 29.2(2) . . . . ?
C3 C2 C10 C12 155.4(2) . . . . ?
C3 C4 C5 C6 64.9(3) . . . . ?
C4 C5 C6 N1 -76.0(3) . . . . ?
C6 N1 C1 C2 2.7(3) . . . . ?
C6 N1 C1 C9 -176.8(2) . . . . ?
C6 N1 C7 C8 177.0(2) . . . . ?
C7 N1 C1 C2 179.6(2) . . . . ?
C7 N1 C1 C9 0.1(3) . . . . ?
C7 N1 C6 C5 -117.7(3) . . . . ?
C7 C8 C9 C1 0.2(3) . . . . ?
C9 C1 C2 C3 116.3(3) . . . . ?
C9 C1 C2 C10 -2.7(4) . . . . ?
C10 C2 C3 O1 -33.7(2) . . . . ?
C10 C2 C3 C4 -153.3(2) . . . . ?
C10 C11 C13 O2 -5.2(4) . . . . ?
C10 C11 C13 C14 174.5(2) . . . . ?
C11 O1 C3 C2 25.1(2) . . . . ?
C11 O1 C3 C4 148.9(2) . . . . ?
C11 C13 C14 O4 -4.2(4) . . . . ?
C11 C13 C14 C15 178.8(3) . . . . ?
C12 C10 C11 O1 -138.5(2) . . . . ?
C12 C10 C11 C13 42.9(4) . . . . ?
C13 O2 C16 O3 179.5(2) . . . . ?
C13 O2 C16 C15 -0.4(3) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C13 C14 C15 C18 -179.9(3) . . . . ?
C14 C15 C16 O2 -0.5(3) . . . . ?
C14 C15 C16 O3 179.6(3) . . . . ?
C16 O2 C13 C11 -179.1(2) . . . . ?
C16 O2 C13 C14 1.1(2) . . . . ?
C17 O4 C14 C13 -166.5(2) . . . . ?
C17 O4 C14 C15 9.6(4) . . . . ?
C18 C15 C16 O2 -179.7(2) . . . . ?
C18 C15 C16 O3 0.4(5) . . . . ?

_olex2_date_sample_data_collection 2020-09-08
_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 1.576
_oxdiff_exptl_absorpt_empirical_full_min 0.519
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2086812'
loop_
_audit_author_name
_audit_author_address
'Xiaodong Wang'
;Lanzhou University
China
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2022-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 N O5'
_chemical_formula_weight         343.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.3435(17)
_cell_length_b                   8.676(2)
_cell_length_c                   13.843(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.933(3)
_cell_angle_gamma                90
_cell_volume                     859.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2351
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      23.93

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   0.5447
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            6522
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.509
_diffrn_reflns_theta_max         26.652
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3526
_reflns_number_gt                2833
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_max     0.945
_reflns_Friedel_fraction_full    0.958

_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.
;

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1064 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3526
_refine_ls_number_parameters     229
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.8192(4) 0.4209(3) 0.67973(19) 0.0421(6) Uani 1 1 d . . . . .
C2 C 0.8146(4) 0.5490(3) 0.60743(18) 0.0411(6) Uani 1 1 d . . . . .
H2 H 0.9399 0.5940 0.6183 0.049 Uiso 1 1 calc R U . . .
C3 C 0.6772(4) 0.6767(3) 0.6162(2) 0.0454(7) Uani 1 1 d . . . . .
H3 H 0.5565 0.6317 0.6199 0.054 Uiso 1 1 calc R U . . .
C4 C 0.7361(4) 0.7925(4) 0.6982(2) 0.0530(7) Uani 1 1 d . . . . .
H4A H 0.6411 0.8718 0.6916 0.064 Uiso 1 1 calc R U . . .
H4B H 0.8510 0.8415 0.6908 0.064 Uiso 1 1 calc R U . . .
C5 C 0.7670(5) 0.7224(3) 0.8016(2) 0.0570(8) Uani 1 1 d . . . . .
H5A H 0.7972 0.8045 0.8502 0.068 Uiso 1 1 calc R U . . .
H5B H 0.6512 0.6754 0.8093 0.068 Uiso 1 1 calc R U . . .
C6 C 0.9201(5) 0.6029(4) 0.8233(2) 0.0564(8) Uani 1 1 d . . . . .
H6A H 1.0258 0.6398 0.7986 0.068 Uiso 1 1 calc R U . . .
H6B H 0.9610 0.5910 0.8946 0.068 Uiso 1 1 calc R U . . .
C7 C 0.8518(4) 0.3155(4) 0.8299(2) 0.0526(8) Uani 1 1 d . . . . .
C8 C 0.8006(4) 0.2011(4) 0.7605(2) 0.0576(8) Uani 1 1 d . . . . .
H8 H 0.7830 0.0978 0.7738 0.069 Uiso 1 1 calc R U . . .
C9 C 0.7797(4) 0.2664(4) 0.6668(2) 0.0502(7) Uani 1 1 d . . . . .
H9 H 0.7453 0.2150 0.6065 0.060 Uiso 1 1 calc R U . . .
C10 C 0.8806(5) 0.2949(5) 0.9348(2) 0.0707(10) Uani 1 1 d . . . . .
H10 H 0.8649 0.1950 0.9559 0.085 Uiso 1 1 calc R U . . .
C11 C 0.7524(4) 0.5037(3) 0.49740(19) 0.0435(7) Uani 1 1 d . . . . .
H11 H 0.6415 0.4378 0.4885 0.052 Uiso 1 1 calc R U . . .
C12 C 0.9040(5) 0.4194(4) 0.4599(2) 0.0665(10) Uani 1 1 d . . . . .
H12A H 1.0036 0.4897 0.4569 0.100 Uiso 1 1 calc R U . . .
H12B H 0.8529 0.3790 0.3949 0.100 Uiso 1 1 calc R U . . .
H12C H 0.9515 0.3363 0.5041 0.100 Uiso 1 1 calc R U . . .
C13 C 0.6955(4) 0.6605(3) 0.4524(2) 0.0441(7) Uani 1 1 d . . . . .
C14 C 0.6865(4) 0.7183(3) 0.3622(2) 0.0468(7) Uani 1 1 d . . . . .
C15 C 0.6596(4) 0.9084(4) 0.2512(3) 0.0646(9) Uani 1 1 d . . . . .
C16 C 0.6657(4) 0.7669(4) 0.1980(2) 0.0569(8) Uani 1 1 d . . . . .
C17 C 0.6815(4) 0.6537(3) 0.2659(2) 0.0485(7) Uani 1 1 d . . . . .
C18 C 0.6817(6) 0.4292(5) 0.1666(2) 0.0876(13) Uani 1 1 d . . . . .
H18A H 0.7941 0.4562 0.1461 0.131 Uiso 1 1 calc R U . . .
H18B H 0.5753 0.4643 0.1180 0.131 Uiso 1 1 calc R U . . .
H18C H 0.6755 0.3193 0.1733 0.131 Uiso 1 1 calc R U . . .
O5 O 0.6504(4) 1.0414(3) 0.2240(2) 0.0925(9) Uani 1 1 d . . . . .
N1 N 0.8632(3) 0.4511(3) 0.77899(16) 0.0465(6) Uani 1 1 d . . . . .
O1 O 0.9229(4) 0.3906(4) 0.99974(18) 0.0940(9) Uani 1 1 d . . . . .
O2 O 0.6589(3) 0.7591(2) 0.52296(14) 0.0525(5) Uani 1 1 d . . . . .
O3 O 0.6658(3) 0.8779(2) 0.35017(16) 0.0580(6) Uani 1 1 d . . . . .
O4 O 0.6821(3) 0.4996(2) 0.25888(15) 0.0608(6) Uani 1 1 d . . . . .
C22 C 0.6446(5) 0.7726(5) 0.0874(2) 0.0885(13) Uani 1 1 d . . . . .
H22A H 0.5177 0.7493 0.0552 0.133 Uiso 1 1 calc R U . . .
H22B H 0.7266 0.6983 0.0680 0.133 Uiso 1 1 calc R U . . .
H22C H 0.6761 0.8739 0.0683 0.133 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
C1 N1 1.365(3) . ?
C1 C9 1.375(4) . ?
C1 C2 1.491(4) . ?
C2 C3 1.521(4) . ?
C2 C11 1.540(3) . ?
C2 H2 0.9800 . ?
C3 O2 1.455(3) . ?
C3 C4 1.505(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.525(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.510(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.473(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.374(4) . ?
C7 N1 1.384(4) . ?
C7 C10 1.430(4) . ?
C8 C9 1.393(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 O1 1.213(4) . ?
C10 H10 0.9300 . ?
C11 C13 1.516(4) . ?
C11 C12 1.518(4) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.333(4) . ?
C13 O2 1.370(3) . ?
C14 O3 1.399(3) . ?
C14 C17 1.439(4) . ?
C15 O5 1.212(4) . ?
C15 O3 1.386(4) . ?
C15 C16 1.437(5) . ?
C16 C17 1.346(4) . ?
C16 C22 1.505(4) . ?
C17 O4 1.340(4) . ?
C18 O4 1.415(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
N1 C1 C9 108.3(2) . . ?
N1 C1 C2 119.8(2) . . ?
C9 C1 C2 131.8(2) . . ?
C1 C2 C3 113.9(2) . . ?
C1 C2 C11 115.5(2) . . ?
C3 C2 C11 102.1(2) . . ?
C1 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
C11 C2 H2 108.3 . . ?
O2 C3 C4 107.2(2) . . ?
O2 C3 C2 102.6(2) . . ?
C4 C3 C2 117.5(2) . . ?
O2 C3 H3 109.7 . . ?
C4 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
C3 C4 C5 113.5(2) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 114.1(3) . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
N1 C6 C5 113.7(2) . . ?
N1 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
N1 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 N1 107.2(2) . . ?
C8 C7 C10 125.1(3) . . ?
N1 C7 C10 127.7(3) . . ?
C7 C8 C9 108.3(3) . . ?
C7 C8 H8 125.9 . . ?
C9 C8 H8 125.9 . . ?
C1 C9 C8 107.4(3) . . ?
C1 C9 H9 126.3 . . ?
C8 C9 H9 126.3 . . ?
O1 C10 C7 128.5(4) . . ?
O1 C10 H10 115.7 . . ?
C7 C10 H10 115.7 . . ?
C13 C11 C12 116.6(2) . . ?
C13 C11 C2 99.9(2) . . ?
C12 C11 C2 112.5(2) . . ?
C13 C11 H11 109.1 . . ?
C12 C11 H11 109.1 . . ?
C2 C11 H11 109.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 O2 117.2(2) . . ?
C14 C13 C11 132.4(3) . . ?
O2 C13 C11 110.3(2) . . ?
C13 C14 O3 117.7(3) . . ?
C13 C14 C17 135.0(3) . . ?
O3 C14 C17 107.2(2) . . ?
O5 C15 O3 118.4(4) . . ?
O5 C15 C16 131.3(3) . . ?
O3 C15 C16 110.2(3) . . ?
C17 C16 C15 105.8(3) . . ?
C17 C16 C22 135.1(4) . . ?
C15 C16 C22 119.0(3) . . ?
O4 C17 C16 132.7(3) . . ?
O4 C17 C14 117.1(3) . . ?
C16 C17 C14 110.1(3) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 C7 108.8(2) . . ?
C1 N1 C6 124.9(2) . . ?
C7 N1 C6 126.3(2) . . ?
C13 O2 C3 109.4(2) . . ?
C15 O3 C14 106.5(3) . . ?
C17 O4 C18 119.8(3) . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -58.9(3) . . . . ?
C9 C1 C2 C3 118.6(3) . . . . ?
N1 C1 C2 C11 -176.6(2) . . . . ?
C9 C1 C2 C11 0.9(4) . . . . ?
C1 C2 C3 O2 -163.9(2) . . . . ?
C11 C2 C3 O2 -38.6(3) . . . . ?
C1 C2 C3 C4 79.0(3) . . . . ?
C11 C2 C3 C4 -155.8(2) . . . . ?
O2 C3 C4 C5 -178.3(2) . . . . ?
C2 C3 C4 C5 -63.6(3) . . . . ?
C3 C4 C5 C6 61.8(3) . . . . ?
C4 C5 C6 N1 -78.4(3) . . . . ?
N1 C7 C8 C9 -0.3(4) . . . . ?
C10 C7 C8 C9 177.9(3) . . . . ?
N1 C1 C9 C8 -0.1(3) . . . . ?
C2 C1 C9 C8 -177.8(3) . . . . ?
C7 C8 C9 C1 0.3(4) . . . . ?
C8 C7 C10 O1 -178.8(4) . . . . ?
N1 C7 C10 O1 -1.0(6) . . . . ?
C1 C2 C11 C13 159.8(2) . . . . ?
C3 C2 C11 C13 35.6(3) . . . . ?
C1 C2 C11 C12 -75.9(3) . . . . ?
C3 C2 C11 C12 160.0(3) . . . . ?
C12 C11 C13 C14 32.9(5) . . . . ?
C2 C11 C13 C14 154.4(3) . . . . ?
C12 C11 C13 O2 -142.5(3) . . . . ?
C2 C11 C13 O2 -21.1(3) . . . . ?
O2 C13 C14 O3 8.5(4) . . . . ?
C11 C13 C14 O3 -166.8(3) . . . . ?
O2 C13 C14 C17 -166.9(3) . . . . ?
C11 C13 C14 C17 17.9(6) . . . . ?
O5 C15 C16 C17 178.1(4) . . . . ?
O3 C15 C16 C17 -1.9(3) . . . . ?
O5 C15 C16 C22 -5.0(5) . . . . ?
O3 C15 C16 C22 175.1(3) . . . . ?
C15 C16 C17 O4 175.3(3) . . . . ?
C22 C16 C17 O4 -0.9(7) . . . . ?
C15 C16 C17 C14 -0.2(3) . . . . ?
C22 C16 C17 C14 -176.4(3) . . . . ?
C13 C14 C17 O4 1.6(5) . . . . ?
O3 C14 C17 O4 -174.1(2) . . . . ?
C13 C14 C17 C16 177.9(3) . . . . ?
O3 C14 C17 C16 2.2(3) . . . . ?
C9 C1 N1 C7 -0.1(3) . . . . ?
C2 C1 N1 C7 178.0(3) . . . . ?
C9 C1 N1 C6 177.9(3) . . . . ?
C2 C1 N1 C6 -4.1(4) . . . . ?
C8 C7 N1 C1 0.2(3) . . . . ?
C10 C7 N1 C1 -177.9(3) . . . . ?
C8 C7 N1 C6 -177.7(3) . . . . ?
C10 C7 N1 C6 4.2(5) . . . . ?
C5 C6 N1 C1 66.8(4) . . . . ?
C5 C6 N1 C7 -115.7(3) . . . . ?
C14 C13 O2 C3 -179.4(3) . . . . ?
C11 C13 O2 C3 -3.2(3) . . . . ?
C4 C3 O2 C13 150.9(2) . . . . ?
C2 C3 O2 C13 26.6(3) . . . . ?
O5 C15 O3 C14 -176.7(3) . . . . ?
C16 C15 O3 C14 3.2(3) . . . . ?
C13 C14 O3 C15 -179.8(3) . . . . ?
C17 C14 O3 C15 -3.3(3) . . . . ?
C16 C17 O4 C18 6.1(5) . . . . ?
C14 C17 O4 C18 -178.5(3) . . . . ?

_refine_diff_density_max         0.121
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.037

