# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_xcalibur
_audit_block_doi                 10.5517/cc13rm2k
_database_code_depnum_ccdc_archive 'CCDC 1035588'
_audit_update_record             
;
2014-11-21 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;
_audit_creation_date             
;
'Fri Oct 11 11:22:09 2013'
;
_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_cell_length_a                   14.9484(16)
_cell_length_b                   9.0889(9)
_cell_length_c                   22.4282(15)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.418(7)
_cell_angle_gamma                90.0
_cell_volume                     3047.1(5)
_cell_measurement_reflns_used    1020
_cell_measurement_theta_min      3.8613
_cell_measurement_theta_max      29.1118
_cell_oxdiff_length_a            14.946(2)
_cell_oxdiff_length_b            9.0967(13)
_cell_oxdiff_length_c            22.412(2)
_cell_oxdiff_angle_alpha         90.027(9)
_cell_oxdiff_angle_beta          90.321(10)
_cell_oxdiff_angle_gamma         90.117(13)
_cell_oxdiff_volume              3047.1(7)
_cell_oxdiff_measurement_reflns_used 1020
_exptl_absorpt_correction_T_min  0.94176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 15.9821
_diffrn_reflns_number            10260
_diffrn_reflns_av_R_equivalents  0.1180
_diffrn_reflns_av_sigmaI/netI    0.2653
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.8613
_diffrn_reflns_theta_max         29.1118
_diffrn_measured_fraction_theta_max 0.8599
_diffrn_reflns_theta_full        26.3154
_diffrn_measured_fraction_theta_full 0.9237
_diffrn_orient_matrix_UB_11      0.0403139000
_diffrn_orient_matrix_UB_12      -0.0381077000
_diffrn_orient_matrix_UB_13      -0.0060148000
_diffrn_orient_matrix_UB_21      0.0069200000
_diffrn_orient_matrix_UB_22      -0.0105973000
_diffrn_orient_matrix_UB_23      0.0310352000
_diffrn_orient_matrix_UB_31      -0.0240657000
_diffrn_orient_matrix_UB_32      -0.0671970000
_diffrn_orient_matrix_UB_33      -0.0015013000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -74.00   -4.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  128.0000  115.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega  -80.00  -47.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -77.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega  -45.00   -2.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -77.0000   60.0000 43

#__ type_ start__ end____ width___ exp.time_
  4 omega   54.00   82.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9803   57.0000  120.0000 28

;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_reflns_odcompleteness_completeness 92.37
_reflns_odcompleteness_theta     26.32
_reflns_odcompleteness_iscentric 1
_chemical_oxdiff_formula         'C32 H35 F1 N2 O5 S1'
_chemical_oxdiff_usercomment     '298K, COLORLESS PLATE, 0.35 0.25 0.04'
####################################################################### 
# 
# 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_suresh
_audit_block_doi                 10.5517/cc14btt3
_database_code_depnum_ccdc_archive 'CCDC 1053095'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 N2 O3'
_chemical_formula_weight         374.43

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7971(8)
_cell_length_b                   11.2067(12)
_cell_length_c                   13.1499(15)
_cell_angle_alpha                83.851(7)
_cell_angle_beta                 81.150(7)
_cell_angle_gamma                76.110(7)
_cell_volume                     958.23(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16822
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         28.36
_reflns_number_total             4758
_reflns_number_gt                2933
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0625P)²+0.4811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4758
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1609
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2776(4) 0.6602(2) 0.53418(16) 0.0524(5) Uani 1 1 d . . .
H1 H 0.4155 0.6282 0.5396 0.063 Uiso 1 1 calc R . .
C2 C 0.1909(4) 0.6256(2) 0.45695(17) 0.0604(6) Uani 1 1 d . . .
H2 H 0.2718 0.5697 0.4115 0.072 Uiso 1 1 calc R . .
C3 C -0.0118(4) 0.6714(2) 0.44537(16) 0.0539(6) Uani 1 1 d . . .
C18 C 0.7097(4) 1.0877(2) 0.7387(3) 0.0703(8) Uani 1 1 d . . .
H9 H 0.8156 1.1286 0.7227 0.084 Uiso 1 1 calc R . .
C6 C 0.1606(3) 0.74224(18) 0.60363(14) 0.0415(5) Uani 1 1 d . . .
C5 C -0.0439(4) 0.7889(2) 0.59295(17) 0.0544(6) Uani 1 1 d . . .
H4 H -0.1253 0.8440 0.6389 0.065 Uiso 1 1 calc R . .
C20 C 0.4207(4) 1.0302(2) 0.69106(19) 0.0580(6) Uani 1 1 d . . .
H7 H 0.3332 1.0333 0.6425 0.070 Uiso 1 1 calc R . .
C4 C -0.1281(4) 0.7541(2) 0.51439(18) 0.0585(6) Uani 1 1 d . . .
H3 H -0.2653 0.7869 0.5080 0.070 Uiso 1 1 calc R . .
C15 C 0.3937(3) 0.96440(17) 0.78587(16) 0.0421(5) Uani 1 1 d . . .
C17 C 0.6833(4) 1.0228(2) 0.8328(2) 0.0645(7) Uani 1 1 d . . .
H10 H 0.7726 1.0196 0.8805 0.077 Uiso 1 1 calc R . .
C16 C 0.5252(3) 0.96219(19) 0.85716(18) 0.0510(5) Uani 1 1 d . . .
H11 H 0.5072 0.9199 0.9215 0.061 Uiso 1 1 calc R . .
C19 C 0.5785(4) 1.0910(2) 0.6695(2) 0.0723(8) Uani 1 1 d . . .
H8 H 0.5954 1.1353 0.6060 0.087 Uiso 1 1 calc R . .
C12 C -0.0348(3) 0.8138(2) 1.03900(16) 0.0465(5) Uani 1 1 d . . .
C10 C 0.0746(3) 0.77143(17) 0.94760(14) 0.0379(4) Uani 1 1 d . . .
C14 C -0.1692(3) 0.6656(2) 0.99286(17) 0.0484(5) Uani 1 1 d . . .
C9 C 0.2525(3) 0.78815(16) 0.87125(14) 0.0367(4) Uani 1 1 d . . .
C8 C 0.2660(3) 0.69197(16) 0.78929(14) 0.0356(4) Uani 1 1 d . . .
C7 C 0.2568(3) 0.77691(17) 0.68831(14) 0.0386(4) Uani 1 1 d . . .
O3 O 0.1371(2) 0.89280(12) 0.72412(10) 0.0423(3) Uani 1 1 d . . .
C11 C 0.0784(3) 0.6344(2) 0.82132(15) 0.0404(4) Uani 1 1 d . . .
C22 C 0.4669(3) 0.59692(17) 0.78690(15) 0.0404(4) Uani 1 1 d . . .
C21 C -0.1058(5) 0.6336(3) 0.36015(19) 0.0746(8) Uani 1 1 d . . .
H5A H -0.2475 0.6752 0.3643 0.112 Uiso 1 1 calc R . .
H5C H -0.0943 0.5461 0.3678 0.112 Uiso 1 1 calc R . .
H5B H -0.0352 0.6554 0.2944 0.112 Uiso 1 1 calc R . .
N1 N 0.2213(2) 0.91025(14) 0.81319(12) 0.0392(4) Uani 1 1 d . . .
N2 N -0.0078(3) 0.68179(15) 0.92099(12) 0.0406(4) Uani 1 1 d . . .
O1 O 0.6138(3) 0.59810(18) 0.72504(16) 0.0849(7) Uani 1 1 d . . .
O2 O 0.4658(3) 0.51223(16) 0.86404(13) 0.0689(5) Uani 1 1 d . . .
C23 C 0.6453(4) 0.4125(2) 0.8672(2) 0.0695(7) Uani 1 1 d . . .
H17B H 0.6257 0.3578 0.9273 0.104 Uiso 1 1 calc R . .
H17A H 0.7622 0.4455 0.8701 0.104 Uiso 1 1 calc R . .
H17C H 0.6672 0.3681 0.8065 0.104 Uiso 1 1 calc R . .
C13 C -0.1877(4) 0.7462(2) 1.06672(18) 0.0508(5) Uiso 1 1 d . . .
H12 H 0.386(3) 0.7710(17) 0.9008(14) 0.034(5) Uiso 1 1 d . . .
H16A H -0.024(3) 0.6646(19) 0.7764(16) 0.043(5) Uiso 1 1 d . . .
H16B H 0.118(3) 0.544(2) 0.8275(16) 0.047(6) Uiso 1 1 d . . .
H13 H -0.007(4) 0.880(2) 1.0760(18) 0.058(7) Uiso 1 1 d . . .
H15 H -0.245(4) 0.608(2) 0.9842(18) 0.057(7) Uiso 1 1 d . . .
H6 H 0.399(3) 0.7824(19) 0.6641(16) 0.046(6) Uiso 1 1 d . . .
H1' H -0.300(4) 0.759(3) 1.134(2) 0.087(9) Uiso 1 1 d . . .


_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 1.381(3) . ?
C1 C6 1.385(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(3) . ?
C3 C21 1.515(3) . ?
C18 C19 1.361(4) . ?
C18 C17 1.376(4) . ?
C18 H9 0.9300 . ?
C6 C5 1.386(3) . ?
C6 C7 1.502(3) . ?
C5 C4 1.387(3) . ?
C5 H4 0.9300 . ?
C20 C19 1.383(3) . ?
C20 C15 1.389(3) . ?
C20 H7 0.9300 . ?
C4 H3 0.9300 . ?
C15 C16 1.386(3) . ?
C15 N1 1.427(2) . ?
C17 C16 1.384(3) . ?
C17 H10 0.9300 . ?
C16 H11 0.9300 . ?
C19 H8 0.9300 . ?
C12 C10 1.379(3) . ?
C12 C13 1.410(3) . ?
C12 H13 1.00(2) . ?
C10 N2 1.360(2) . ?
C10 C9 1.484(3) . ?
C14 N2 1.367(3) . ?
C14 C13 1.368(3) . ?
C14 H15 0.94(2) . ?
C9 N1 1.479(2) . ?
C9 C8 1.582(3) . ?
C9 H12 1.011(19) . ?
C8 C22 1.516(3) . ?
C8 C11 1.546(3) . ?
C8 C7 1.549(3) . ?
C7 O3 1.441(2) . ?
C7 H6 0.98(2) . ?
O3 N1 1.4310(19) . ?
C11 N2 1.452(2) . ?
C11 H16A 0.96(2) . ?
C11 H16B 0.98(2) . ?
C22 O1 1.189(2) . ?
C22 O2 1.313(2) . ?
C21 H5A 0.9600 . ?
C21 H5C 0.9600 . ?
C21 H5B 0.9600 . ?
O2 C23 1.446(3) . ?
C23 H17B 0.9600 . ?
C23 H17A 0.9600 . ?
C23 H17C 0.9600 . ?
C13 H1' 1.07(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 121.8(2) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 117.6(2) . . ?
C2 C3 C21 121.6(2) . . ?
C4 C3 C21 120.8(2) . . ?
C19 C18 C17 119.0(2) . . ?
C19 C18 H9 120.5 . . ?
C17 C18 H9 120.5 . . ?
C1 C6 C5 118.32(19) . . ?
C1 C6 C7 119.60(19) . . ?
C5 C6 C7 122.07(18) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H4 119.7 . . ?
C4 C5 H4 119.7 . . ?
C19 C20 C15 119.5(2) . . ?
C19 C20 H7 120.3 . . ?
C15 C20 H7 120.3 . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 H3 119.4 . . ?
C5 C4 H3 119.4 . . ?
C16 C15 C20 119.0(2) . . ?
C16 C15 N1 120.38(18) . . ?
C20 C15 N1 120.30(19) . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H10 119.7 . . ?
C16 C17 H10 119.7 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H11 119.9 . . ?
C15 C16 H11 119.9 . . ?
C18 C19 C20 121.7(2) . . ?
C18 C19 H8 119.2 . . ?
C20 C19 H8 119.2 . . ?
C10 C12 C13 106.58(19) . . ?
C10 C12 H13 124.8(14) . . ?
C13 C12 H13 128.6(14) . . ?
N2 C10 C12 107.90(18) . . ?
N2 C10 C9 110.56(16) . . ?
C12 C10 C9 141.51(19) . . ?
N2 C14 C13 107.1(2) . . ?
N2 C14 H15 120.3(14) . . ?
C13 C14 H15 132.5(15) . . ?
N1 C9 C10 113.72(16) . . ?
N1 C9 C8 105.68(14) . . ?
C10 C9 C8 103.83(15) . . ?
N1 C9 H12 109.2(11) . . ?
C10 C9 H12 114.3(11) . . ?
C8 C9 H12 109.6(11) . . ?
C22 C8 C11 112.70(16) . . ?
C22 C8 C7 111.49(15) . . ?
C11 C8 C7 114.27(16) . . ?
C22 C8 C9 110.24(15) . . ?
C11 C8 C9 106.25(15) . . ?
C7 C8 C9 101.09(14) . . ?
O3 C7 C6 109.08(15) . . ?
O3 C7 C8 102.46(14) . . ?
C6 C7 C8 117.99(16) . . ?
O3 C7 H6 110.6(12) . . ?
C6 C7 H6 110.9(12) . . ?
C8 C7 H6 105.4(12) . . ?
N1 O3 C7 105.41(13) . . ?
N2 C11 C8 103.46(15) . . ?
N2 C11 H16A 106.5(12) . . ?
C8 C11 H16A 111.8(13) . . ?
N2 C11 H16B 110.7(12) . . ?
C8 C11 H16B 111.5(13) . . ?
H16A C11 H16B 112.3(18) . . ?
O1 C22 O2 122.22(19) . . ?
O1 C22 C8 125.31(18) . . ?
O2 C22 C8 112.44(17) . . ?
C3 C21 H5A 109.5 . . ?
C3 C21 H5C 109.5 . . ?
H5A C21 H5C 109.5 . . ?
C3 C21 H5B 109.5 . . ?
H5A C21 H5B 109.5 . . ?
H5C C21 H5B 109.5 . . ?
C15 N1 O3 111.72(14) . . ?
C15 N1 C9 117.74(15) . . ?
O3 N1 C9 104.22(13) . . ?
C10 N2 C14 110.03(17) . . ?
C10 N2 C11 115.07(16) . . ?
C14 N2 C11 134.57(18) . . ?
C22 O2 C23 117.69(18) . . ?
O2 C23 H17B 109.5 . . ?
O2 C23 H17A 109.5 . . ?
H17B C23 H17A 109.5 . . ?
O2 C23 H17C 109.5 . . ?
H17B C23 H17C 109.5 . . ?
H17A C23 H17C 109.5 . . ?
C14 C13 C12 108.4(2) . . ?
C14 C13 H1' 126.7(15) . . ?
C12 C13 H1' 124.9(15) . . ?

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
C6 C1 C2 C3 0.6(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 C21 179.7(2) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C1 C6 C7 178.9(2) . . . . ?
C1 C6 C5 C4 -0.1(3) . . . . ?
C7 C6 C5 C4 -179.4(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C21 C3 C4 C5 179.7(2) . . . . ?
C6 C5 C4 C3 0.6(4) . . . . ?
C19 C20 C15 C16 0.6(3) . . . . ?
C19 C20 C15 N1 174.4(2) . . . . ?
C19 C18 C17 C16 -0.3(4) . . . . ?
C18 C17 C16 C15 1.3(4) . . . . ?
C20 C15 C16 C17 -1.3(3) . . . . ?
N1 C15 C16 C17 -175.19(19) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
C15 C20 C19 C18 0.4(4) . . . . ?
C13 C12 C10 N2 -0.1(2) . . . . ?
C13 C12 C10 C9 -177.9(2) . . . . ?
N2 C10 C9 N1 115.02(17) . . . . ?
C12 C10 C9 N1 -67.3(3) . . . . ?
N2 C10 C9 C8 0.7(2) . . . . ?
C12 C10 C9 C8 178.4(2) . . . . ?
N1 C9 C8 C22 122.49(16) . . . . ?
C10 C9 C8 C22 -117.56(17) . . . . ?
N1 C9 C8 C11 -115.11(16) . . . . ?
C10 C9 C8 C11 4.85(19) . . . . ?
N1 C9 C8 C7 4.45(18) . . . . ?
C10 C9 C8 C7 124.41(16) . . . . ?
C1 C6 C7 O3 158.28(18) . . . . ?
C5 C6 C7 O3 -22.4(3) . . . . ?
C1 C6 C7 C8 -85.5(2) . . . . ?
C5 C6 C7 C8 93.8(2) . . . . ?
C22 C8 C7 O3 -146.69(15) . . . . ?
C11 C8 C7 O3 84.09(18) . . . . ?
C9 C8 C7 O3 -29.56(18) . . . . ?
C22 C8 C7 C6 93.5(2) . . . . ?
C11 C8 C7 C6 -35.7(2) . . . . ?
C9 C8 C7 C6 -149.33(17) . . . . ?
C6 C7 O3 N1 172.13(14) . . . . ?
C8 C7 O3 N1 46.33(17) . . . . ?
C22 C8 C11 N2 112.61(17) . . . . ?
C7 C8 C11 N2 -118.78(17) . . . . ?
C9 C8 C11 N2 -8.22(19) . . . . ?
C11 C8 C22 O1 142.1(2) . . . . ?
C7 C8 C22 O1 12.0(3) . . . . ?
C9 C8 C22 O1 -99.4(3) . . . . ?
C11 C8 C22 O2 -39.9(2) . . . . ?
C7 C8 C22 O2 -169.96(17) . . . . ?
C9 C8 C22 O2 78.6(2) . . . . ?
C16 C15 N1 O3 -164.68(17) . . . . ?
C20 C15 N1 O3 21.5(2) . . . . ?
C16 C15 N1 C9 -44.1(3) . . . . ?
C20 C15 N1 C9 142.09(19) . . . . ?
C7 O3 N1 C15 84.42(17) . . . . ?
C7 O3 N1 C9 -43.73(17) . . . . ?
C10 C9 N1 C15 144.95(17) . . . . ?
C8 C9 N1 C15 -101.82(18) . . . . ?
C10 C9 N1 O3 -90.68(17) . . . . ?
C8 C9 N1 O3 22.55(18) . . . . ?
C12 C10 N2 C14 0.4(2) . . . . ?
C9 C10 N2 C14 178.89(16) . . . . ?
C12 C10 N2 C11 174.81(17) . . . . ?
C9 C10 N2 C11 -6.7(2) . . . . ?
C13 C14 N2 C10 -0.5(2) . . . . ?
C13 C14 N2 C11 -173.4(2) . . . . ?
C8 C11 N2 C10 9.5(2) . . . . ?
C8 C11 N2 C14 -177.9(2) . . . . ?
O1 C22 O2 C23 -5.2(4) . . . . ?
C8 C22 O2 C23 176.8(2) . . . . ?
N2 C14 C13 C12 0.4(2) . . . . ?
C10 C12 C13 C14 -0.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.042
