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

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

data_exp_7669
_database_code_depnum_ccdc_archive 'CCDC 2211267'
loop_
_audit_author_name
_audit_author_address
'Jian Hao' 'Beijing University of Chemical Technology'
_audit_update_record             
;
2022-10-05 deposited with the CCDC.	2022-12-01 downloaded from the CCDC.
;
_audit_creation_date             2021-12-03
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            1H-isothiochromene
_chemical_name_systematic        
;
 Dimethyl 1-(diphenylphosphoryl)-1H-isothiochromene-3,4-dicarboxylate 
;
_chemical_formula_moiety         'C25 H21 O5 P S'
_chemical_formula_sum            'C25 H21 O5 P S'
_chemical_formula_weight         464.45
_chemical_melting_point          '181-182 deg'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.9928(5)
_cell_length_b                   17.2209(6)
_cell_length_c                   13.4103(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.451(4)
_cell_angle_gamma                90.00
_cell_volume                     2224.31(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2780
_cell_measurement_temperature    114.85(10)
_cell_measurement_theta_max      25.8650
_cell_measurement_theta_min      3.7800
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18570
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.15
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      114.85(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.8589
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00   18.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -57.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  2 omega  -16.00   11.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -40.00   24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -57.0000 -150.0000 64

#__ type_ start__ end____ width___ exp.time_
  4 omega  -13.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   19.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega  -10.00   78.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   77.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega  -37.00    0.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508   77.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
  7 omega  -25.00   24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000  150.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0381494000
_diffrn_orient_matrix_UB_12      0.0349447000
_diffrn_orient_matrix_UB_13      -0.0133654000
_diffrn_orient_matrix_UB_21      0.0602619000
_diffrn_orient_matrix_UB_22      0.0217822000
_diffrn_orient_matrix_UB_23      0.0239617000
_diffrn_orient_matrix_UB_31      0.0184093000
_diffrn_orient_matrix_UB_32      0.0011344000
_diffrn_orient_matrix_UB_33      -0.0475127000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3276
_reflns_number_total             4339
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0352P)²+0.9233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1054
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.38220(7) 0.21132(3) 0.64493(4) 0.01917(16) Uani 1 1 d . . .
S1 S 0.07228(7) 0.18571(3) 0.57973(4) 0.02079(16) Uani 1 1 d . . .
O3 O -0.03716(18) 0.26325(9) 0.81930(12) 0.0269(4) Uani 1 1 d . . .
O4 O -0.01810(18) 0.42266(9) 0.74730(11) 0.0251(4) Uani 1 1 d . . .
O1 O 0.39136(18) 0.25139(9) 0.74405(11) 0.0247(4) Uani 1 1 d . . .
O2 O -0.08293(19) 0.15797(9) 0.71661(12) 0.0272(4) Uani 1 1 d . . .
O5 O 0.19379(18) 0.38558(10) 0.84030(12) 0.0275(4) Uani 1 1 d . . .
C5 C 0.2001(2) 0.31402(13) 0.52260(16) 0.0181(5) Uani 1 1 d . . .
C3 C 0.0998(2) 0.32811(13) 0.67424(16) 0.0183(5) Uani 1 1 d . . .
C2 C 0.0541(2) 0.25419(13) 0.67225(16) 0.0178(5) Uani 1 1 d . . .
C10 C -0.0243(3) 0.22721(13) 0.74555(17) 0.0198(5) Uani 1 1 d . . .
C6 C 0.2385(3) 0.34671(14) 0.43945(17) 0.0230(6) Uani 1 1 d . . .
H6 H 0.2699 0.3150 0.3943 0.028 Uiso 1 1 calc R . .
C1 C 0.2191(2) 0.22806(13) 0.54460(17) 0.0189(5) Uani 1 1 d . . .
H1 H 0.2270 0.2025 0.4811 0.023 Uiso 1 1 calc R . .
C20 C 0.5147(3) 0.24372(13) 0.58551(17) 0.0191(5) Uani 1 1 d . . .
C14 C 0.4046(3) 0.10760(13) 0.66020(17) 0.0204(5) Uani 1 1 d . . .
C12 C 0.0983(3) 0.38015(13) 0.76443(17) 0.0210(5) Uani 1 1 d . . .
C21 C 0.5277(3) 0.21573(14) 0.49102(18) 0.0247(6) Uani 1 1 d . . .
H21 H 0.4633 0.1805 0.4534 0.030 Uiso 1 1 calc R . .
C15 C 0.3707(3) 0.05524(14) 0.57838(18) 0.0261(6) Uani 1 1 d . . .
H15 H 0.3233 0.0723 0.5126 0.031 Uiso 1 1 calc R . .
C19 C 0.4707(3) 0.08057(14) 0.75948(18) 0.0240(6) Uani 1 1 d . . .
H19 H 0.4910 0.1147 0.8153 0.029 Uiso 1 1 calc R . .
C4 C 0.1517(2) 0.36160(13) 0.59079(16) 0.0187(5) Uani 1 1 d . . .
C25 C 0.6099(3) 0.29836(13) 0.63860(18) 0.0244(6) Uani 1 1 d . . .
H25 H 0.6014 0.3182 0.7011 0.029 Uiso 1 1 calc R . .
C24 C 0.7168(3) 0.32329(15) 0.59939(19) 0.0293(6) Uani 1 1 d . . .
H24 H 0.7789 0.3605 0.6350 0.035 Uiso 1 1 calc R . .
C23 C 0.7321(3) 0.29363(15) 0.50816(19) 0.0281(6) Uani 1 1 d . . .
H23 H 0.8063 0.3092 0.4833 0.034 Uiso 1 1 calc R . .
C9 C 0.1455(3) 0.44178(13) 0.57354(18) 0.0228(5) Uani 1 1 d . . .
H9 H 0.1147 0.4742 0.6183 0.027 Uiso 1 1 calc R . .
C22 C 0.6368(3) 0.24039(15) 0.45321(18) 0.0272(6) Uani 1 1 d . . .
H22 H 0.6460 0.2211 0.3906 0.033 Uiso 1 1 calc R . .
C8 C 0.1842(3) 0.47343(15) 0.49119(18) 0.0284(6) Uani 1 1 d . . .
H8 H 0.1795 0.5269 0.4809 0.034 Uiso 1 1 calc R . .
C18 C 0.5061(3) 0.00246(15) 0.77436(19) 0.0300(6) Uani 1 1 d . . .
H18 H 0.5498 -0.0156 0.8404 0.036 Uiso 1 1 calc R . .
C7 C 0.2302(3) 0.42619(14) 0.42361(18) 0.0273(6) Uani 1 1 d . . .
H7 H 0.2554 0.4478 0.3677 0.033 Uiso 1 1 calc R . .
C16 C 0.4071(3) -0.02210(14) 0.5945(2) 0.0307(6) Uani 1 1 d . . .
H16 H 0.3846 -0.0568 0.5393 0.037 Uiso 1 1 calc R . .
C17 C 0.4769(3) -0.04839(15) 0.6920(2) 0.0316(6) Uani 1 1 d . . .
H17 H 0.5040 -0.1001 0.7019 0.038 Uiso 1 1 calc R . .
C11 C -0.1704(3) 0.12889(15) 0.7780(2) 0.0365(7) Uani 1 1 d . . .
H11A H -0.2139 0.0815 0.7482 0.055 Uiso 1 1 calc R . .
H11B H -0.2404 0.1667 0.7796 0.055 Uiso 1 1 calc R . .
H11C H -0.1151 0.1191 0.8472 0.055 Uiso 1 1 calc R . .
C13 C -0.0332(3) 0.46794(16) 0.83487(19) 0.0366(7) Uani 1 1 d . . .
H13A H -0.1190 0.4962 0.8156 0.055 Uiso 1 1 calc R . .
H13B H 0.0428 0.5037 0.8555 0.055 Uiso 1 1 calc R . .
H13C H -0.0335 0.4338 0.8914 0.055 Uiso 1 1 calc R . .


_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
P1 O1 1.4786(16) . ?
P1 C1 1.839(2) . ?
P1 C20 1.806(2) . ?
P1 C14 1.805(2) . ?
S1 C2 1.756(2) . ?
S1 C1 1.809(2) . ?
O3 C10 1.203(3) . ?
O4 C12 1.341(3) . ?
O4 C13 1.451(3) . ?
O2 C10 1.340(3) . ?
O2 C11 1.441(3) . ?
O5 C12 1.199(3) . ?
C5 C6 1.391(3) . ?
C5 C1 1.511(3) . ?
C5 C4 1.406(3) . ?
C3 C2 1.350(3) . ?
C3 C12 1.509(3) . ?
C3 C4 1.471(3) . ?
C2 C10 1.485(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(3) . ?
C1 H1 0.9800 . ?
C20 C21 1.394(3) . ?
C20 C25 1.392(3) . ?
C14 C15 1.391(3) . ?
C14 C19 1.399(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.392(3) . ?
C4 C9 1.399(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.378(3) . ?
C24 H24 0.9300 . ?
C24 C23 1.372(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.385(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.376(3) . ?
C22 H22 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.384(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.378(3) . ?
C7 H7 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.384(3) . ?
C17 H17 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
O1 P1 C1 114.53(10) . . ?
O1 P1 C20 112.04(10) . . ?
O1 P1 C14 112.56(10) . . ?
C20 P1 C1 103.88(10) . . ?
C14 P1 C1 107.28(11) . . ?
C14 P1 C20 105.82(10) . . ?
C2 S1 C1 99.04(11) . . ?
C12 O4 C13 115.29(18) . . ?
C10 O2 C11 115.38(18) . . ?
C6 C5 C1 120.4(2) . . ?
C6 C5 C4 120.1(2) . . ?
C4 C5 C1 119.39(19) . . ?
C2 C3 C12 120.01(19) . . ?
C2 C3 C4 122.7(2) . . ?
C4 C3 C12 117.26(19) . . ?
C3 C2 S1 123.29(17) . . ?
C3 C2 C10 121.1(2) . . ?
C10 C2 S1 115.45(16) . . ?
O3 C10 O2 124.3(2) . . ?
O3 C10 C2 125.0(2) . . ?
O2 C10 C2 110.71(18) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.8 . . ?
P1 C1 H1 107.7 . . ?
S1 C1 P1 111.62(12) . . ?
S1 C1 H1 107.7 . . ?
C5 C1 P1 109.70(16) . . ?
C5 C1 S1 112.17(16) . . ?
C5 C1 H1 107.7 . . ?
C21 C20 P1 123.46(18) . . ?
C25 C20 P1 117.70(17) . . ?
C25 C20 C21 118.8(2) . . ?
C15 C14 P1 123.74(17) . . ?
C15 C14 C19 119.3(2) . . ?
C19 C14 P1 116.75(18) . . ?
O4 C12 C3 112.36(19) . . ?
O5 C12 O4 124.1(2) . . ?
O5 C12 C3 123.4(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C19 H19 120.1 . . ?
C18 C19 C14 119.7(2) . . ?
C18 C19 H19 120.1 . . ?
C5 C4 C3 121.2(2) . . ?
C9 C4 C5 118.4(2) . . ?
C9 C4 C3 120.2(2) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 C20 120.6(2) . . ?
C24 C25 H25 119.7 . . ?
C25 C24 H24 119.8 . . ?
C23 C24 C25 120.4(2) . . ?
C23 C24 H24 119.8 . . ?
C24 C23 H23 120.1 . . ?
C24 C23 C22 119.8(2) . . ?
C22 C23 H23 120.1 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 120.9(2) . . ?
C8 C9 H9 119.5 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.8 . . ?
C9 C8 H8 119.8 . . ?
C9 C8 C7 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C19 C18 H18 119.7 . . ?
C17 C18 C19 120.5(2) . . ?
C17 C18 H18 119.7 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(2) . . ?
C8 C7 H7 120.1 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.5(2) . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
P1 C20 C21 C22 -176.49(19) . . . . ?
P1 C20 C25 C24 177.52(19) . . . . ?
P1 C14 C15 C16 171.7(2) . . . . ?
P1 C14 C19 C18 -172.40(19) . . . . ?
S1 C2 C10 O3 173.28(19) . . . . ?
S1 C2 C10 O2 -8.7(3) . . . . ?
O1 P1 C1 S1 -66.41(15) . . . . ?
O1 P1 C1 C5 58.55(18) . . . . ?
O1 P1 C20 C21 -179.21(19) . . . . ?
O1 P1 C20 C25 2.1(2) . . . . ?
O1 P1 C14 C15 165.2(2) . . . . ?
O1 P1 C14 C19 -20.3(2) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C5 C4 C9 C8 0.7(4) . . . . ?
C3 C2 C10 O3 -10.6(4) . . . . ?
C3 C2 C10 O2 167.5(2) . . . . ?
C3 C4 C9 C8 -175.3(2) . . . . ?
C2 S1 C1 P1 75.43(13) . . . . ?
C2 S1 C1 C5 -48.14(17) . . . . ?
C2 C3 C12 O4 -93.4(3) . . . . ?
C2 C3 C12 O5 90.3(3) . . . . ?
C2 C3 C4 C5 -21.5(4) . . . . ?
C2 C3 C4 C9 154.3(2) . . . . ?
C6 C5 C1 P1 97.0(2) . . . . ?
C6 C5 C1 S1 -138.3(2) . . . . ?
C6 C5 C4 C3 175.0(2) . . . . ?
C6 C5 C4 C9 -0.9(3) . . . . ?
C1 P1 C20 C21 -55.1(2) . . . . ?
C1 P1 C20 C25 126.29(19) . . . . ?
C1 P1 C14 C15 38.4(2) . . . . ?
C1 P1 C14 C19 -147.20(18) . . . . ?
C1 S1 C2 C3 23.9(2) . . . . ?
C1 S1 C2 C10 -160.00(17) . . . . ?
C1 C5 C6 C7 -175.5(2) . . . . ?
C1 C5 C4 C3 -9.1(3) . . . . ?
C1 C5 C4 C9 175.0(2) . . . . ?
C20 P1 C1 S1 171.06(11) . . . . ?
C20 P1 C1 C5 -63.98(17) . . . . ?
C20 P1 C14 C15 -72.1(2) . . . . ?
C20 P1 C14 C19 102.36(19) . . . . ?
C20 C21 C22 C23 -0.9(4) . . . . ?
C20 C25 C24 C23 -1.0(4) . . . . ?
C14 P1 C1 S1 59.29(14) . . . . ?
C14 P1 C1 C5 -175.75(15) . . . . ?
C14 P1 C20 C21 57.8(2) . . . . ?
C14 P1 C20 C25 -120.88(19) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C14 C19 C18 C17 0.2(4) . . . . ?
C12 C3 C2 S1 -171.52(18) . . . . ?
C12 C3 C2 C10 12.6(3) . . . . ?
C12 C3 C4 C5 158.8(2) . . . . ?
C12 C3 C4 C9 -25.4(3) . . . . ?
C21 C20 C25 C24 -1.2(4) . . . . ?
C15 C14 C19 C18 2.3(4) . . . . ?
C15 C16 C17 C18 2.2(4) . . . . ?
C19 C14 C15 C16 -2.6(4) . . . . ?
C19 C18 C17 C16 -2.5(4) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C4 C5 C1 P1 -78.9(2) . . . . ?
C4 C5 C1 S1 45.8(3) . . . . ?
C4 C3 C2 S1 8.8(3) . . . . ?
C4 C3 C2 C10 -167.1(2) . . . . ?
C4 C3 C12 O4 86.3(3) . . . . ?
C4 C3 C12 O5 -90.0(3) . . . . ?
C4 C9 C8 C7 0.1(4) . . . . ?
C25 C20 C21 C22 2.1(3) . . . . ?
C25 C24 C23 C22 2.3(4) . . . . ?
C24 C23 C22 C21 -1.4(4) . . . . ?
C9 C8 C7 C6 -0.6(4) . . . . ?
C11 O2 C10 O3 2.5(3) . . . . ?
C11 O2 C10 C2 -175.5(2) . . . . ?
C13 O4 C12 O5 -9.9(3) . . . . ?
C13 O4 C12 C3 173.77(19) . . . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_8106
_database_code_depnum_ccdc_archive 'CCDC 2211268'
loop_
_audit_author_name
_audit_author_address
'Jian Hao' 'Beijing University of Chemical Technology'
_audit_update_record             
;
2022-10-05 deposited with the CCDC.	2022-12-01 downloaded from the CCDC.
;
_audit_creation_date             2022-08-17
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            indolizine
_chemical_name_systematic        
;
 Dimethyl 5-methyl-1-phenylindolizine-2,3-dicarboxylate 
;
_chemical_formula_moiety         'C19 H17 N O4'
_chemical_formula_sum            'C19 H17 N O4'
_chemical_formula_weight         323.34
_chemical_melting_point          '114-115 deg'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   38.4079(16)
_cell_length_b                   10.3454(5)
_cell_length_c                   7.9044(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3140.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2493
_cell_measurement_temperature    112.85(10)
_cell_measurement_theta_max      25.5610
_cell_measurement_theta_min      4.4660
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12029
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.29
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      112.85(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9936
_diffrn_measured_fraction_theta_max 0.8618
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -61.00   -4.00   0.3000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070  -37.0000   30.0000 190

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   27.20   0.3000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070  -99.0000  -30.0000 174

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00    3.20   0.3000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070  -99.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega  -51.00   21.00   0.3000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -37.0000 -180.0000 240
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0036882000
_diffrn_orient_matrix_UB_12      -0.0134763000
_diffrn_orient_matrix_UB_13      0.0861275000
_diffrn_orient_matrix_UB_21      -0.0175028000
_diffrn_orient_matrix_UB_22      0.0197828000
_diffrn_orient_matrix_UB_23      -0.0123940000
_diffrn_orient_matrix_UB_31      -0.0046144000
_diffrn_orient_matrix_UB_32      -0.0642211000
_diffrn_orient_matrix_UB_33      -0.0219610000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2368
_reflns_number_total             3052
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0376P)²+1.2157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1135
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.57068(3) 0.37518(11) 0.02316(17) 0.0229(3) Uani 1 1 d . . .
O2 O 0.54750(3) 0.55284(12) -0.22805(17) 0.0241(3) Uani 1 1 d . . .
O1 O 0.53293(3) 0.70635(13) -0.03841(18) 0.0297(4) Uani 1 1 d . . .
O3 O 0.61364(4) 0.31504(13) -0.1528(2) 0.0337(4) Uani 1 1 d . . .
N1 N 0.61246(4) 0.74708(15) -0.0272(2) 0.0205(4) Uani 1 1 d . . .
C10 C 0.59983(5) 0.39648(18) -0.0671(2) 0.0214(4) Uani 1 1 d . . .
C2 C 0.61237(5) 0.53096(18) -0.0445(2) 0.0209(4) Uani 1 1 d . . .
C8 C 0.60665(5) 0.87985(18) -0.0497(2) 0.0229(5) Uani 1 1 d . . .
C4 C 0.64482(5) 0.70151(18) 0.0319(2) 0.0206(4) Uani 1 1 d . . .
C12 C 0.66827(5) 0.37148(18) 0.1667(3) 0.0254(5) Uani 1 1 d . . .
H12 H 0.6457 0.3520 0.2014 0.030 Uiso 1 1 calc R . .
C1 C 0.59233(5) 0.64087(17) -0.0730(2) 0.0209(4) Uani 1 1 d . . .
C18 C 0.51086(5) 0.5307(2) -0.2576(3) 0.0308(5) Uani 1 1 d . . .
H18A H 0.5080 0.4597 -0.3346 0.046 Uiso 1 1 calc R . .
H18B H 0.5006 0.6070 -0.3054 0.046 Uiso 1 1 calc R . .
H18C H 0.4996 0.5107 -0.1524 0.046 Uiso 1 1 calc R . .
C5 C 0.66931(5) 0.79154(18) 0.0938(3) 0.0260(5) Uani 1 1 d . . .
H5 H 0.6902 0.7629 0.1401 0.031 Uiso 1 1 calc R . .
C3 C 0.64506(5) 0.56674(18) 0.0190(2) 0.0206(4) Uani 1 1 d . . .
C11 C 0.67424(5) 0.48125(18) 0.0679(2) 0.0221(4) Uani 1 1 d . . .
C9 C 0.55493(5) 0.64225(18) -0.1093(2) 0.0217(4) Uani 1 1 d . . .
C6 C 0.66233(5) 0.91995(19) 0.0856(3) 0.0294(5) Uani 1 1 d . . .
H6 H 0.6780 0.9796 0.1298 0.035 Uiso 1 1 calc R . .
C7 C 0.63122(5) 0.96210(19) 0.0098(3) 0.0269(5) Uani 1 1 d . . .
H7 H 0.6273 1.0505 0.0000 0.032 Uiso 1 1 calc R . .
C16 C 0.70831(5) 0.50734(19) 0.0164(3) 0.0278(5) Uani 1 1 d . . .
H16 H 0.7128 0.5798 -0.0497 0.033 Uiso 1 1 calc R . .
C19 C 0.55550(5) 0.24850(18) 0.0036(3) 0.0268(5) Uani 1 1 d . . .
H19A H 0.5545 0.2267 -0.1144 0.040 Uiso 1 1 calc R . .
H19B H 0.5324 0.2484 0.0497 0.040 Uiso 1 1 calc R . .
H19C H 0.5695 0.1860 0.0623 0.040 Uiso 1 1 calc R . .
C14 C 0.72900(6) 0.3184(2) 0.1617(3) 0.0375(6) Uani 1 1 d . . .
H14 H 0.7472 0.2643 0.1931 0.045 Uiso 1 1 calc R . .
C13 C 0.69548(5) 0.2913(2) 0.2136(3) 0.0320(5) Uani 1 1 d . . .
H13 H 0.6912 0.2190 0.2803 0.038 Uiso 1 1 calc R . .
C17 C 0.57513(5) 0.92308(19) -0.1424(3) 0.0284(5) Uani 1 1 d . . .
H17A H 0.5718 0.8697 -0.2404 0.043 Uiso 1 1 calc R . .
H17B H 0.5780 1.0114 -0.1770 0.043 Uiso 1 1 calc R . .
H17C H 0.5552 0.9161 -0.0698 0.043 Uiso 1 1 calc R . .
C15 C 0.73555(5) 0.4262(2) 0.0628(3) 0.0359(5) Uani 1 1 d . . .
H15 H 0.7581 0.4443 0.0274 0.043 Uiso 1 1 calc R . .


_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
O4 C10 1.346(2) . ?
O4 C19 1.443(2) . ?
O2 C18 1.445(2) . ?
O2 C9 1.348(2) . ?
O1 C9 1.211(2) . ?
O3 C10 1.204(2) . ?
N1 C8 1.403(2) . ?
N1 C4 1.409(2) . ?
N1 C1 1.391(2) . ?
C10 C2 1.483(3) . ?
C2 C1 1.391(3) . ?
C2 C3 1.402(3) . ?
C8 C7 1.355(3) . ?
C8 C17 1.484(3) . ?
C4 C5 1.411(3) . ?
C4 C3 1.398(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.397(3) . ?
C12 C13 1.385(3) . ?
C1 C9 1.465(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C6 1.357(3) . ?
C3 C11 1.479(3) . ?
C11 C16 1.397(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.406(3) . ?
C7 H7 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.390(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C13 1.380(3) . ?
C14 C15 1.385(3) . ?
C13 H13 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O4 C19 115.34(14) . . ?
C9 O2 C18 115.30(15) . . ?
C8 N1 C4 120.66(15) . . ?
C1 N1 C8 130.68(16) . . ?
C1 N1 C4 108.18(15) . . ?
O4 C10 C2 111.10(15) . . ?
O3 C10 O4 123.38(17) . . ?
O3 C10 C2 125.51(18) . . ?
C1 C2 C10 124.59(17) . . ?
C1 C2 C3 109.72(16) . . ?
C3 C2 C10 125.56(17) . . ?
N1 C8 C17 119.17(17) . . ?
C7 C8 N1 117.39(18) . . ?
C7 C8 C17 123.39(18) . . ?
N1 C4 C5 118.82(16) . . ?
C3 C4 N1 108.39(15) . . ?
C3 C4 C5 132.77(17) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C13 C12 C11 120.85(19) . . ?
N1 C1 C9 126.02(16) . . ?
C2 C1 N1 107.22(16) . . ?
C2 C1 C9 125.59(17) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.86(18) . . ?
C6 C5 H5 120.1 . . ?
C2 C3 C11 127.90(17) . . ?
C4 C3 C2 106.46(16) . . ?
C4 C3 C11 125.62(17) . . ?
C12 C11 C3 120.53(17) . . ?
C16 C11 C12 118.28(18) . . ?
C16 C11 C3 121.19(17) . . ?
O2 C9 C1 109.71(16) . . ?
O1 C9 O2 123.37(18) . . ?
O1 C9 C1 126.76(18) . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.47(19) . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 123.03(19) . . ?
C8 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.06(19) . . ?
C15 C14 H14 120.0 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C8 C17 H17A 109.5 . . ?
C8 C17 H17B 109.5 . . ?
C8 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C15 H15 120.1 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.1 . . ?

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
O4 C10 C2 C1 -54.6(3) . . . . ?
O4 C10 C2 C3 120.8(2) . . . . ?
O3 C10 C2 C1 126.1(2) . . . . ?
O3 C10 C2 C3 -58.5(3) . . . . ?
N1 C8 C7 C6 2.6(3) . . . . ?
N1 C4 C5 C6 -4.2(3) . . . . ?
N1 C4 C3 C2 -1.3(2) . . . . ?
N1 C4 C3 C11 -179.95(18) . . . . ?
N1 C1 C9 O2 147.49(18) . . . . ?
N1 C1 C9 O1 -37.0(3) . . . . ?
C10 C2 C1 N1 176.05(17) . . . . ?
C10 C2 C1 C9 7.8(3) . . . . ?
C10 C2 C3 C4 -175.19(18) . . . . ?
C10 C2 C3 C11 3.4(3) . . . . ?
C2 C1 C9 O2 -46.5(3) . . . . ?
C2 C1 C9 O1 129.0(2) . . . . ?
C2 C3 C11 C12 -45.8(3) . . . . ?
C2 C3 C11 C16 133.8(2) . . . . ?
C8 N1 C4 C5 10.1(3) . . . . ?
C8 N1 C4 C3 -171.54(16) . . . . ?
C8 N1 C1 C2 171.10(18) . . . . ?
C8 N1 C1 C9 -20.7(3) . . . . ?
C4 N1 C8 C7 -9.2(3) . . . . ?
C4 N1 C8 C17 168.28(17) . . . . ?
C4 N1 C1 C2 -0.8(2) . . . . ?
C4 N1 C1 C9 167.35(18) . . . . ?
C4 C5 C6 C7 -2.3(3) . . . . ?
C4 C3 C11 C12 132.5(2) . . . . ?
C4 C3 C11 C16 -47.8(3) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
C1 N1 C8 C7 179.72(19) . . . . ?
C1 N1 C8 C17 -2.8(3) . . . . ?
C1 N1 C4 C5 -177.00(17) . . . . ?
C1 N1 C4 C3 1.3(2) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C1 C2 C3 C11 179.42(19) . . . . ?
C18 O2 C9 O1 -4.4(3) . . . . ?
C18 O2 C9 C1 171.20(16) . . . . ?
C5 C4 C3 C2 176.7(2) . . . . ?
C5 C4 C3 C11 -1.9(3) . . . . ?
C5 C6 C7 C8 3.2(3) . . . . ?
C3 C2 C1 N1 0.0(2) . . . . ?
C3 C2 C1 C9 -168.23(18) . . . . ?
C3 C4 C5 C6 178.0(2) . . . . ?
C3 C11 C16 C15 -179.86(19) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C11 C16 C15 C14 -0.2(3) . . . . ?
C19 O4 C10 O3 -3.4(3) . . . . ?
C19 O4 C10 C2 177.30(16) . . . . ?
C13 C12 C11 C3 -179.71(19) . . . . ?
C13 C12 C11 C16 0.6(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C17 C8 C7 C6 -174.81(19) . . . . ?
C15 C14 C13 C12 0.2(3) . . . . ?
