# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_cu_cc1vket44_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1447002'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'3 R ,4 R )-Methyl 1-oxo-3-phenyl-3-(trifluoromethyl)isochrom an-4-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 F3 O4'
_chemical_formula_weight         350.28

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'P 61'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'

_cell_length_a                   9.0807(3)
_cell_length_b                   9.0807(3)
_cell_length_c                   33.7042(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2406.87(14)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(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    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    1.081
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            16841
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         5.63
_diffrn_reflns_theta_max         66.55
_reflns_number_total             2290
_reflns_number_gt                2288
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0414P)²+0.0000P] 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       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_number_reflns         2290
_refine_ls_number_parameters     228
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.463
_refine_ls_restrained_S_all      1.440
_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
F001 F 0.52612(11) 1.11140(10) 0.11101(3) 0.0274(2) Uani 1 1 d U . .
F002 F 0.28089(10) 0.97184(10) 0.08346(3) 0.0280(2) Uani 1 1 d U . .
O003 O 0.45502(10) 0.80670(10) 0.08091(3) 0.0167(2) Uani 1 1 d U . .
O10 O 0.43167(11) 0.55818(11) 0.09233(3) 0.0225(2) Uani 1 1 d U . .
O005 O 0.16726(12) 0.89306(11) 0.00215(3) 0.0237(2) Uani 1 1 d U . .
F006 F 0.48024(13) 1.19253(10) 0.05426(3) 0.0351(2) Uani 1 1 d U . .
O007 O 0.14369(11) 0.65994(12) 0.03160(3) 0.0218(2) Uani 1 1 d U . .
C008 C 0.45606(13) 0.66438(15) 0.06791(4) 0.0162(3) Uani 1 1 d U . .
C009 C 0.22880(14) 0.79779(15) 0.01703(4) 0.0165(3) Uani 1 1 d U . .
C00A C 0.47254(13) 0.76261(14) -0.00208(4) 0.0153(3) Uani 1 1 d U . .
C00B C 0.70381(15) 1.04914(14) 0.05141(4) 0.0188(3) Uani 1 1 d U . .
C00C C 0.48618(14) 0.65395(15) 0.02511(4) 0.0168(3) Uani 1 1 d U . .
C00D C 0.44831(19) 1.05694(16) 0.07604(5) 0.0227(3) Uani 1 1 d U . .
C00E C 0.49727(15) 0.74763(16) -0.04213(4) 0.0201(3) Uani 1 1 d U . .
H00E H 0.4901 0.8225 -0.0607 0.024 Uiso 1 1 calc R . .
C00F C 0.50925(15) 0.94837(14) 0.05421(4) 0.0161(3) Uani 1 1 d U . .
C00G C 0.42285(14) 0.88794(13) 0.01331(4) 0.0155(3) Uani 1 1 d U . .
H00G H 0.4639 0.9867 -0.0052 0.019 Uiso 1 1 calc R . .
C00H C 0.52259(16) 0.52989(15) 0.01193(5) 0.0232(3) Uani 1 1 d U . .
H00H H 0.5317 0.4560 0.0305 0.028 Uiso 1 1 calc R . .
C00I C 0.80052(17) 1.02688(16) 0.08017(5) 0.0235(3) Uani 1 1 d U . .
H00I H 0.7457 0.9453 0.1006 0.028 Uiso 1 1 calc R . .
C00J C 0.54531(18) 0.51476(17) -0.02797(5) 0.0279(3) Uani 1 1 d U . .
H00J H 0.5697 0.4300 -0.0369 0.033 Uiso 1 1 calc R . .
C00K C 0.53267(16) 0.62277(17) -0.05518(5) 0.0256(3) Uani 1 1 d U . .
H00K H 0.5481 0.6117 -0.0827 0.031 Uiso 1 1 calc R . .
C00L C 0.97745(19) 1.12353(19) 0.07924(5) 0.0322(4) Uani 1 1 d U . .
H00L H 1.0429 1.1084 0.0991 0.039 Uiso 1 1 calc R . .
C00M C 0.78528(18) 1.16866(16) 0.02143(5) 0.0266(3) Uani 1 1 d U . .
H00M H 0.7203 1.1848 0.0016 0.032 Uiso 1 1 calc R . .
C00N C 1.05722(18) 1.24118(19) 0.04943(6) 0.0348(4) Uani 1 1 d U . .
H00N H 1.1778 1.3065 0.0486 0.042 Uiso 1 1 calc R . .
C00O C 0.9617(2) 1.26415(18) 0.02065(5) 0.0343(4) Uani 1 1 d U . .
H00O H 1.0172 1.3457 0.0002 0.041 Uiso 1 1 calc R . .
C00P C -0.01415(19) 0.8218(2) 0.00740(5) 0.0326(3) Uani 1 1 d U . .
H00A H -0.0748 0.7111 -0.0059 0.049 Uiso 1 1 calc R . .
H00B H -0.0490 0.8987 -0.0041 0.049 Uiso 1 1 calc R . .
H00C H -0.0414 0.8072 0.0358 0.049 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
F001 C00D 1.3355(19) . ?
F002 C00D 1.3402(18) . ?
O003 C008 1.3692(16) . ?
O003 C00F 1.4402(15) . ?
O10 C008 1.2012(17) . ?
O005 C009 1.3400(16) . ?
O005 C00P 1.4483(17) . ?
F006 C00D 1.3347(17) . ?
O007 C009 1.1991(16) . ?
C008 C00C 1.480(2) . ?
C009 C00G 1.5325(15) . ?
C00A C00E 1.3861(19) . ?
C00A C00C 1.3968(19) . ?
C00A C00G 1.5104(16) . ?
C00B C00I 1.389(2) . ?
C00B C00M 1.3940(19) . ?
C00B C00F 1.5333(16) . ?
C00C C00H 1.3957(18) . ?
C00D C00F 1.5379(17) . ?
C00E C00K 1.395(2) . ?
C00F C00G 1.5447(18) . ?
C00H C00J 1.378(2) . ?
C00I C00L 1.394(2) . ?
C00J C00K 1.389(2) . ?
C00L C00N 1.379(3) . ?
C00M C00O 1.389(2) . ?
C00N C00O 1.385(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
C008 O003 C00F 118.84(10) . . ?
C009 O005 C00P 114.46(11) . . ?
O10 C008 O003 116.94(13) . . ?
O10 C008 C00C 125.61(12) . . ?
O003 C008 C00C 117.45(11) . . ?
O007 C009 O005 124.61(11) . . ?
O007 C009 C00G 124.05(11) . . ?
O005 C009 C00G 111.33(10) . . ?
C00E C00A C00C 119.58(11) . . ?
C00E C00A C00G 122.17(11) . . ?
C00C C00A C00G 118.19(12) . . ?
C00I C00B C00M 119.41(12) . . ?
C00I C00B C00F 119.60(12) . . ?
C00M C00B C00F 120.92(13) . . ?
C00H C00C C00A 120.13(13) . . ?
C00H C00C C008 119.18(12) . . ?
C00A C00C C008 120.65(11) . . ?
F006 C00D F001 108.24(10) . . ?
F006 C00D F002 107.17(11) . . ?
F001 C00D F002 106.64(12) . . ?
F006 C00D C00F 110.27(12) . . ?
F001 C00D C00F 111.49(11) . . ?
F002 C00D C00F 112.81(10) . . ?
C00A C00E C00K 120.08(13) . . ?
O003 C00F C00B 110.42(10) . . ?
O003 C00F C00D 101.63(10) . . ?
C00B C00F C00D 108.87(10) . . ?
O003 C00F C00G 110.75(9) . . ?
C00B C00F C00G 112.72(11) . . ?
C00D C00F C00G 111.90(10) . . ?
C00A C00G C009 108.82(9) . . ?
C00A C00G C00F 106.51(10) . . ?
C009 C00G C00F 111.15(11) . . ?
C00J C00H C00C 119.92(13) . . ?
C00B C00I C00L 120.42(13) . . ?
C00H C00J C00K 120.31(12) . . ?
C00J C00K C00E 119.98(14) . . ?
C00N C00L C00I 119.87(16) . . ?
C00O C00M C00B 119.81(14) . . ?
C00L C00N C00O 120.07(14) . . ?
C00N C00O C00M 120.42(14) . . ?

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
C00F O003 C008 O10 170.54(10) . . . . ?
C00F O003 C008 C00C -9.75(13) . . . . ?
C00P O005 C009 O007 4.2(2) . . . . ?
C00P O005 C009 C00G -175.46(12) . . . . ?
C00E C00A C00C C00H -0.72(18) . . . . ?
C00G C00A C00C C00H 176.48(10) . . . . ?
C00E C00A C00C C008 -178.43(10) . . . . ?
C00G C00A C00C C008 -1.23(15) . . . . ?
O10 C008 C00C C00H -13.24(17) . . . . ?
O003 C008 C00C C00H 167.08(10) . . . . ?
O10 C008 C00C C00A 164.50(12) . . . . ?
O003 C008 C00C C00A -15.19(15) . . . . ?
C00C C00A C00E C00K 1.09(18) . . . . ?
C00G C00A C00E C00K -175.99(10) . . . . ?
C008 O003 C00F C00B -77.74(12) . . . . ?
C008 O003 C00F C00D 166.86(9) . . . . ?
C008 O003 C00F C00G 47.83(13) . . . . ?
C00I C00B C00F O003 -16.86(16) . . . . ?
C00M C00B C00F O003 166.13(12) . . . . ?
C00I C00B C00F C00D 93.91(13) . . . . ?
C00M C00B C00F C00D -83.10(16) . . . . ?
C00I C00B C00F C00G -141.31(12) . . . . ?
C00M C00B C00F C00G 41.68(15) . . . . ?
F006 C00D C00F O003 -176.71(10) . . . . ?
F001 C00D C00F O003 63.02(13) . . . . ?
F002 C00D C00F O003 -56.94(14) . . . . ?
F006 C00D C00F C00B 66.75(14) . . . . ?
F001 C00D C00F C00B -53.51(15) . . . . ?
F002 C00D C00F C00B -173.47(12) . . . . ?
F006 C00D C00F C00G -58.51(14) . . . . ?
F001 C00D C00F C00G -178.77(10) . . . . ?
F002 C00D C00F C00G 61.27(15) . . . . ?
C00E C00A C00G C009 93.94(14) . . . . ?
C00C C00A C00G C009 -83.19(13) . . . . ?
C00E C00A C00G C00F -146.16(11) . . . . ?
C00C C00A C00G C00F 36.72(13) . . . . ?
O007 C009 C00G C00A 45.77(18) . . . . ?
O005 C009 C00G C00A -134.57(12) . . . . ?
O007 C009 C00G C00F -71.21(15) . . . . ?
O005 C009 C00G C00F 108.45(12) . . . . ?
O003 C00F C00G C00A -59.02(12) . . . . ?
C00B C00F C00G C00A 65.25(12) . . . . ?
C00D C00F C00G C00A -171.65(10) . . . . ?
O003 C00F C00G C009 59.36(12) . . . . ?
C00B C00F C00G C009 -176.37(9) . . . . ?
C00D C00F C00G C009 -53.27(13) . . . . ?
C00A C00C C00H C00J 0.08(18) . . . . ?
C008 C00C C00H C00J 177.82(11) . . . . ?
C00M C00B C00I C00L 0.3(2) . . . . ?
C00F C00B C00I C00L -176.77(13) . . . . ?
C00C C00H C00J C00K 0.20(19) . . . . ?
C00H C00J C00K C00E 0.2(2) . . . . ?
C00A C00E C00K C00J -0.82(19) . . . . ?
C00B C00I C00L C00N -0.5(2) . . . . ?
C00I C00B C00M C00O -0.1(2) . . . . ?
C00F C00B C00M C00O 176.92(13) . . . . ?
C00I C00L C00N C00O 0.5(2) . . . . ?
C00L C00N C00O C00M -0.3(2) . . . . ?
C00B C00M C00O C00N 0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        66.55
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.032
####################################################################### 
# 
# 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_cu_cc210_0m
_database_code_depnum_ccdc_archive 'CCDC 1447003'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'3 S ,4 R )-3-(Ethoxycarbonyl)-1-oxo-3-(thiophen-2-yl)isochro mane-4-carboxylic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 O6 S '
_chemical_formula_weight         61.08

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.5357(3)
_cell_length_b                   12.3308(4)
_cell_length_c                   14.9954(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1578.30(9)
_cell_formula_units_Z            26
_cell_measurement_temperature    100(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    1.671
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             806
_exptl_absorpt_coefficient_mu    8.837
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            6216
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.64
_diffrn_reflns_theta_max         64.87
_reflns_number_total             2574
_reflns_number_gt                2506
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1001P)²+1.5854P] 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       0.0004(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(4)
_refine_ls_number_reflns         2574
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1591
_refine_ls_wR_factor_gt          0.1582
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.005

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
S1 S 0.20045(15) 0.50515(9) 1.00084(8) 0.0405(4) Uani 1 1 d . . .
O5 O 0.2655(3) 0.4528(2) 0.71680(17) 0.0235(6) Uani 1 1 d . . .
O2 O 0.5041(4) 0.6830(2) 0.73615(17) 0.0259(6) Uani 1 1 d . . .
C17 C 0.5078(4) 0.7032(3) 0.8144(2) 0.0179(7) Uani 1 1 d . . .
C14 C 0.3373(4) 0.3284(2) 0.9363(2) 0.0117(7) Uani 1 1 d . . .
H14 H 0.4034 0.2805 0.9039 0.014 Uiso 1 1 calc R . .
C5 C 0.6808(5) 0.6334(3) 1.1021(3) 0.0271(9) Uani 1 1 d . . .
H5 H 0.6845 0.6714 1.1571 0.032 Uiso 1 1 calc R . .
C2 C 0.6672(4) 0.5215(3) 0.9427(2) 0.0207(8) Uani 1 1 d . . .
C8 C 0.6596(4) 0.4573(3) 0.8592(3) 0.0204(8) Uani 1 1 d . . .
C10 C 0.2709(4) 0.5217(3) 0.7744(2) 0.0166(7) Uani 1 1 d . . .
C11 C 0.0312(5) 0.5960(3) 0.7244(3) 0.0270(8) Uani 1 1 d . . .
H11A H -0.0266 0.5272 0.7329 0.032 Uiso 1 1 calc R . .
H11B H 0.0666 0.5999 0.6616 0.032 Uiso 1 1 calc R . .
C6 C 0.5708(5) 0.6633(3) 1.0380(2) 0.0223(8) Uani 1 1 d . . .
H6 H 0.5013 0.7220 1.0487 0.027 Uiso 1 1 calc R . .
C1 C 0.5642(4) 0.6062(3) 0.9582(2) 0.0192(7) Uani 1 1 d . . .
C12 C -0.0719(6) 0.6893(5) 0.7450(4) 0.0523(15) Uani 1 1 d . . .
H12A H -0.1046 0.6857 0.8076 0.078 Uiso 1 1 calc R . .
H12B H -0.1646 0.6869 0.7065 0.078 Uiso 1 1 calc R . .
H12C H -0.0148 0.7571 0.7346 0.078 Uiso 1 1 calc R . .
C4 C 0.7844(5) 0.5493(3) 1.0869(3) 0.0288(9) Uani 1 1 d . . .
H4 H 0.8583 0.5296 1.1315 0.035 Uiso 1 1 calc R . .
C13 C 0.3150(4) 0.4506(3) 0.9229(2) 0.0195(8) Uani 1 1 d . . .
C15 C 0.2362(6) 0.3035(4) 1.0084(4) 0.0476(12) Uani 1 1 d . . .
H15 H 0.2217 0.2309 1.0279 0.057 Uiso 1 1 calc R . .
C9 C 0.3905(4) 0.5181(3) 0.8505(2) 0.0170(7) Uani 1 1 d . . .
C7 C 0.4422(5) 0.6294(3) 0.8866(2) 0.0182(8) Uani 1 1 d . . .
H7 H 0.3500 0.6658 0.9148 0.022 Uiso 1 1 calc R . .
C3 C 0.7802(4) 0.4939(3) 1.0073(3) 0.0263(8) Uani 1 1 d . . .
H3 H 0.8532 0.4375 0.9959 0.032 Uiso 1 1 calc R . .
C16 C 0.1611(5) 0.3869(4) 1.0485(3) 0.0314(10) Uani 1 1 d . . .
H16 H 0.0935 0.3787 1.0984 0.038 Uiso 1 1 calc R . .
O6 O 0.1668(3) 0.59990(19) 0.78457(16) 0.0202(6) Uani 1 1 d . . .
O4 O 0.7635(3) 0.4025(2) 0.82980(18) 0.0260(6) Uani 1 1 d . . .
O3 O 0.5219(3) 0.46098(19) 0.81259(17) 0.0187(6) Uani 1 1 d . . .
O1 O 0.5670(4) 0.7917(2) 0.85101(17) 0.0255(6) Uani 1 1 d . . .
H1 H 0.6045 0.8317 0.8110 0.038 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
S1 C16 1.658(4) . ?
S1 C13 1.665(4) . ?
O5 C10 1.212(4) . ?
O2 C17 1.199(5) . ?
C17 O1 1.323(4) . ?
C17 C7 1.521(5) . ?
C14 C15 1.417(6) . ?
C14 C13 1.533(5) . ?
C5 C4 1.382(6) . ?
C5 C6 1.393(6) . ?
C2 C1 1.385(5) . ?
C2 C3 1.408(5) . ?
C2 C8 1.483(5) . ?
C8 O4 1.199(5) . ?
C8 O3 1.369(5) . ?
C10 O6 1.320(4) . ?
C10 C9 1.532(5) . ?
C11 O6 1.468(5) . ?
C11 C12 1.481(6) . ?
C6 C1 1.389(5) . ?
C1 C7 1.523(5) . ?
C4 C3 1.376(6) . ?
C13 C9 1.513(5) . ?
C15 C16 1.353(7) . ?
C9 O3 1.441(4) . ?
C9 C7 1.540(5) . ?

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
C16 S1 C13 93.8(2) . . ?
O2 C17 O1 126.0(3) . . ?
O2 C17 C7 124.2(3) . . ?
O1 C17 C7 109.8(3) . . ?
C15 C14 C13 103.7(3) . . ?
C4 C5 C6 121.1(4) . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 C8 121.1(3) . . ?
C3 C2 C8 118.8(3) . . ?
O4 C8 O3 117.8(3) . . ?
O4 C8 C2 125.4(4) . . ?
O3 C8 C2 116.8(3) . . ?
O5 C10 O6 124.7(3) . . ?
O5 C10 C9 122.4(3) . . ?
O6 C10 C9 112.5(3) . . ?
O6 C11 C12 108.4(3) . . ?
C1 C6 C5 119.2(4) . . ?
C2 C1 C6 120.0(3) . . ?
C2 C1 C7 117.2(3) . . ?
C6 C1 C7 122.7(3) . . ?
C3 C4 C5 119.9(4) . . ?
C9 C13 C14 125.6(3) . . ?
C9 C13 S1 122.2(3) . . ?
C14 C13 S1 112.2(2) . . ?
C16 C15 C14 117.6(4) . . ?
O3 C9 C13 110.2(3) . . ?
O3 C9 C10 103.8(3) . . ?
C13 C9 C10 105.5(3) . . ?
O3 C9 C7 110.5(3) . . ?
C13 C9 C7 111.1(3) . . ?
C10 C9 C7 115.3(3) . . ?
C17 C7 C1 111.3(3) . . ?
C17 C7 C9 112.9(3) . . ?
C1 C7 C9 106.1(3) . . ?
C4 C3 C2 119.7(4) . . ?
C15 C16 S1 112.4(3) . . ?
C10 O6 C11 115.8(3) . . ?
C8 O3 C9 118.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        64.87
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.869
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.091
####################################################################### 
# 
# 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_cu_cc195_0m
_database_code_depnum_ccdc_archive 'CCDC 1447004'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"(2 R ,3 S )-Methyl 1'-benzyl-3-(4-nitrophenyl)-2',5-dioxo-4,5 -dihydro-3H-spiro[furan-2,3'- indoline]-3-carboxylate"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 N2 O7'
_chemical_formula_weight         472.44

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   8.2334(4)
_cell_length_b                   12.8730(6)
_cell_length_c                   11.1784(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.114(2)
_cell_angle_gamma                90.00
_cell_volume                     1132.32(9)
_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    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    0.852
_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     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            5726
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         66.21
_reflns_number_total             3094
_reflns_number_gt                2671
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0100P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(12)
_refine_ls_number_reflns         3094
_refine_ls_number_parameters     317
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0653
_refine_ls_wR_factor_gt          0.0644
_refine_ls_goodness_of_fit_ref   1.899
_refine_ls_restrained_S_all      1.899
_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
O1 O 0.55457(17) 0.35241(11) 0.40499(10) 0.0311(4) Uani 1 1 d . . .
O2 O 0.5367(2) 0.45204(12) 0.55602(10) 0.0407(4) Uani 1 1 d . . .
O3 O 1.00515(15) 0.78703(12) 0.29624(10) 0.0302(4) Uani 1 1 d . . .
O4 O 0.43987(15) 0.90143(11) -0.00447(10) 0.0265(3) Uani 1 1 d . . .
O5 O 0.33597(14) 0.74850(10) 0.03443(10) 0.0232(3) Uani 1 1 d . . .
O6 O 0.77685(19) 1.05114(12) 0.14837(13) 0.0393(4) Uani 1 1 d . . .
O7 O 0.80187(14) 0.89306(10) 0.07260(10) 0.0237(3) Uani 1 1 d . . .
N2 N 0.55206(19) 0.43857(13) 0.45149(12) 0.0258(4) Uani 1 1 d . . .
N3 N 0.98134(18) 0.65902(14) 0.14844(13) 0.0230(4) Uani 1 1 d . . .
C1 C 1.0448(2) 0.34007(18) 0.42217(16) 0.0342(6) Uani 1 1 d . . .
H1 H 1.0247 0.2837 0.4679 0.041 Uiso 1 1 calc R . .
C2 C 1.1192(2) 0.32541(17) 0.32814(15) 0.0313(6) Uani 1 1 d . . .
H2 H 1.1503 0.2590 0.3105 0.038 Uiso 1 1 calc R . .
C3 C 1.1478(2) 0.40960(17) 0.25964(15) 0.0262(5) Uani 1 1 d . . .
H3 H 1.1977 0.3990 0.1960 0.031 Uiso 1 1 calc R . .
C4 C 1.1029(2) 0.50955(16) 0.28466(14) 0.0229(5) Uani 1 1 d . . .
C5 C 1.0294(2) 0.52344(17) 0.38057(15) 0.0322(6) Uani 1 1 d . . .
H5 H 0.9998 0.5899 0.3993 0.039 Uiso 1 1 calc R . .
C6 C 1.0000(3) 0.4397(2) 0.44834(17) 0.0365(6) Uani 1 1 d . . .
H6 H 0.9499 0.4500 0.5119 0.044 Uiso 1 1 calc R . .
C7 C 0.57255(19) 0.51634(15) 0.25567(13) 0.0200(5) Uani 1 1 d . . .
H7 H 0.5660 0.4501 0.2214 0.024 Uiso 1 1 calc R . .
C8 C 0.5692(2) 0.53045(15) 0.37780(13) 0.0199(5) Uani 1 1 d . . .
C9 C 0.5792(2) 0.62743(15) 0.43060(13) 0.0250(5) Uani 1 1 d . . .
H9 H 0.5756 0.6353 0.5125 0.030 Uiso 1 1 calc R . .
C10 C 0.5949(2) 0.71339(16) 0.36042(15) 0.0240(5) Uani 1 1 d . . .
H10 H 0.6017 0.7793 0.3956 0.029 Uiso 1 1 calc R . .
C11 C 0.6005(2) 0.70227(14) 0.23745(13) 0.0176(4) Uani 1 1 d . . .
C12 C 0.5857(2) 0.60227(15) 0.18613(13) 0.0203(4) Uani 1 1 d . . .
H12 H 0.5848 0.5938 0.1033 0.024 Uiso 1 1 calc R . .
C13 C 0.7461(2) 0.71399(15) -0.00778(14) 0.0202(4) Uani 1 1 d . . .
C14 C 0.8700(2) 0.63826(15) 0.02656(14) 0.0203(4) Uani 1 1 d . . .
C15 C 0.8800(2) 0.55640(16) -0.05080(16) 0.0250(5) Uani 1 1 d . . .
H15 H 0.9640 0.5059 -0.0261 0.030 Uiso 1 1 calc R . .
C16 C 0.7578(2) 0.55317(17) -0.16792(15) 0.0285(5) Uani 1 1 d . . .
H16 H 0.7612 0.4997 -0.2231 0.034 Uiso 1 1 calc R . .
C17 C 0.6319(2) 0.62789(16) -0.20357(14) 0.0265(5) Uani 1 1 d . . .
H17 H 0.5513 0.6234 -0.2817 0.032 Uiso 1 1 calc R . .
C18 C 0.6247(2) 0.70942(16) -0.12404(14) 0.0234(5) Uani 1 1 d . . .
H18 H 0.5404 0.7598 -0.1481 0.028 Uiso 1 1 calc R . .
C19 C 0.4545(2) 0.82196(15) 0.05406(14) 0.0201(5) Uani 1 1 d . . .
C20 C 1.1358(2) 0.60102(16) 0.21069(16) 0.0278(5) Uani 1 1 d . . .
H20A H 1.2163 0.6474 0.2665 0.033 Uiso 1 1 calc R . .
H20B H 1.1870 0.5764 0.1482 0.033 Uiso 1 1 calc R . .
C21 C 0.9322(2) 0.74589(16) 0.19682(14) 0.0214(5) Uani 1 1 d . . .
C22 C 0.1834(2) 0.77275(16) -0.06704(14) 0.0278(5) Uani 1 1 d . . .
H22A H 0.2138 0.7866 -0.1421 0.042 Uiso 1 1 calc R . .
H22B H 0.1292 0.8329 -0.0452 0.042 Uiso 1 1 calc R . .
H22C H 0.1067 0.7148 -0.0807 0.042 Uiso 1 1 calc R . .
C23 C 0.6178(2) 0.79647(14) 0.16074(13) 0.0190(5) Uani 1 1 d . . .
C24 C 0.7670(2) 0.78742(15) 0.10107(13) 0.0191(4) Uani 1 1 d . . .
C25 C 0.7503(2) 0.95968(16) 0.15135(16) 0.0271(5) Uani 1 1 d . . .
C26 C 0.6672(2) 0.89997(15) 0.23213(13) 0.0214(4) Uani 1 1 d . . .
H26A H 0.5676 0.9361 0.2403 0.026 Uiso 1 1 calc R . .
H26B H 0.7455 0.8884 0.3148 0.026 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
O1 N2 1.228(2) . ?
O2 N2 1.2240(19) . ?
O3 C21 1.2180(19) . ?
O4 C19 1.201(2) . ?
O5 C19 1.330(2) . ?
O5 C22 1.4573(17) . ?
O6 C25 1.200(2) . ?
O7 C25 1.382(2) . ?
O7 C24 1.444(2) . ?
N2 C8 1.472(2) . ?
N3 C21 1.355(2) . ?
N3 C14 1.4259(18) . ?
N3 C20 1.462(2) . ?
C1 C2 1.376(3) . ?
C1 C6 1.389(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 C20 1.508(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.374(2) . ?
C7 C8 1.386(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.396(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.400(2) . ?
C11 C23 1.516(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(3) . ?
C13 C18 1.388(2) . ?
C13 C24 1.510(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.397(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C23 1.547(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C24 1.557(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C26 1.545(2) . ?
C23 C24 1.566(3) . ?
C25 C26 1.496(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O5 C22 113.50(13) . . ?
C25 O7 C24 109.00(14) . . ?
O2 N2 O1 123.47(16) . . ?
O2 N2 C8 118.32(17) . . ?
O1 N2 C8 118.21(15) . . ?
C21 N3 C14 110.64(14) . . ?
C21 N3 C20 123.48(13) . . ?
C14 N3 C20 125.70(17) . . ?
C2 C1 C6 119.5(2) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 120.94(19) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.47(19) . . ?
C5 C4 C20 120.79(18) . . ?
C3 C4 C20 120.73(17) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C12 C7 C8 118.66(17) . . ?
C12 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C9 C8 C7 121.78(16) . . ?
C9 C8 N2 119.58(15) . . ?
C7 C8 N2 118.64(16) . . ?
C8 C9 C10 119.15(15) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C11 120.77(17) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 118.27(16) . . ?
C10 C11 C23 120.71(16) . . ?
C12 C11 C23 121.00(14) . . ?
C7 C12 C11 121.33(15) . . ?
C7 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C18 119.99(18) . . ?
C14 C13 C24 108.55(12) . . ?
C18 C13 C24 131.35(17) . . ?
C15 C14 C13 122.68(13) . . ?
C15 C14 N3 126.96(17) . . ?
C13 C14 N3 110.36(16) . . ?
C14 C15 C16 116.76(18) . . ?
C14 C15 H15 121.6 . . ?
C16 C15 H15 121.6 . . ?
C17 C16 C15 121.38(18) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 120.72(13) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 118.47(17) . . ?
C17 C18 H18 120.8 . . ?
C13 C18 H18 120.8 . . ?
O4 C19 O5 124.37(13) . . ?
O4 C19 C23 121.72(17) . . ?
O5 C19 C23 113.91(15) . . ?
N3 C20 C4 112.84(16) . . ?
N3 C20 H20A 109.0 . . ?
C4 C20 H20A 109.0 . . ?
N3 C20 H20B 109.0 . . ?
C4 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
O3 C21 N3 126.72(15) . . ?
O3 C21 C24 125.06(18) . . ?
N3 C21 C24 108.19(13) . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C23 C26 116.88(13) . . ?
C11 C23 C19 113.64(14) . . ?
C26 C23 C19 104.62(15) . . ?
C11 C23 C24 113.42(15) . . ?
C26 C23 C24 99.42(14) . . ?
C19 C23 C24 107.47(13) . . ?
O7 C24 C13 113.25(14) . . ?
O7 C24 C21 106.55(13) . . ?
C13 C24 C21 102.03(15) . . ?
O7 C24 C23 104.80(15) . . ?
C13 C24 C23 118.18(15) . . ?
C21 C24 C23 111.65(14) . . ?
O6 C25 O7 119.9(2) . . ?
O6 C25 C26 129.8(2) . . ?
O7 C25 C26 110.27(17) . . ?
C25 C26 C23 103.25(15) . . ?
C25 C26 H26A 111.1 . . ?
C23 C26 H26A 111.1 . . ?
C25 C26 H26B 111.1 . . ?
C23 C26 H26B 111.1 . . ?
H26A C26 H26B 109.1 . . ?

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
C6 C1 C2 C3 -0.5(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C2 C3 C4 C20 179.41(13) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C20 C4 C5 C6 -179.78(13) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C12 C7 C8 C9 -0.2(2) . . . . ?
C12 C7 C8 N2 178.94(14) . . . . ?
O2 N2 C8 C9 4.4(2) . . . . ?
O1 N2 C8 C9 -175.30(16) . . . . ?
O2 N2 C8 C7 -174.75(15) . . . . ?
O1 N2 C8 C7 5.5(2) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
N2 C8 C9 C10 -179.83(15) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C12 1.5(2) . . . . ?
C9 C10 C11 C23 -179.95(15) . . . . ?
C8 C7 C12 C11 1.8(2) . . . . ?
C10 C11 C12 C7 -2.5(2) . . . . ?
C23 C11 C12 C7 179.03(15) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
C24 C13 C14 C15 176.87(18) . . . . ?
C18 C13 C14 N3 179.40(18) . . . . ?
C24 C13 C14 N3 -4.0(2) . . . . ?
C21 N3 C14 C15 -179.74(19) . . . . ?
C20 N3 C14 C15 4.9(3) . . . . ?
C21 N3 C14 C13 1.2(2) . . . . ?
C20 N3 C14 C13 -174.17(18) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
N3 C14 C15 C16 -178.77(19) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C13 -0.3(3) . . . . ?
C14 C13 C18 C17 -0.2(3) . . . . ?
C24 C13 C18 C17 -176.0(2) . . . . ?
C22 O5 C19 O4 0.3(3) . . . . ?
C22 O5 C19 C23 -179.42(16) . . . . ?
C21 N3 C20 C4 96.6(2) . . . . ?
C14 N3 C20 C4 -88.6(2) . . . . ?
C5 C4 C20 N3 -58.60(19) . . . . ?
C3 C4 C20 N3 122.38(17) . . . . ?
C14 N3 C21 O3 -176.16(19) . . . . ?
C20 N3 C21 O3 -0.7(3) . . . . ?
C14 N3 C21 C24 2.1(2) . . . . ?
C20 N3 C21 C24 177.54(18) . . . . ?
C10 C11 C23 C26 12.8(2) . . . . ?
C12 C11 C23 C26 -168.71(16) . . . . ?
C10 C11 C23 C19 -109.23(18) . . . . ?
C12 C11 C23 C19 69.2(2) . . . . ?
C10 C11 C23 C24 127.63(17) . . . . ?
C12 C11 C23 C24 -53.91(18) . . . . ?
O4 C19 C23 C11 170.07(17) . . . . ?
O5 C19 C23 C11 -10.1(2) . . . . ?
O4 C19 C23 C26 41.5(2) . . . . ?
O5 C19 C23 C26 -138.77(16) . . . . ?
O4 C19 C23 C24 -63.6(2) . . . . ?
O5 C19 C23 C24 116.20(17) . . . . ?
C25 O7 C24 C13 155.32(14) . . . . ?
C25 O7 C24 C21 -93.32(16) . . . . ?
C25 O7 C24 C23 25.14(13) . . . . ?
C14 C13 C24 O7 118.96(16) . . . . ?
C18 C13 C24 O7 -64.9(3) . . . . ?
C14 C13 C24 C21 4.8(2) . . . . ?
C18 C13 C24 C21 -179.0(2) . . . . ?
C14 C13 C24 C23 -117.97(17) . . . . ?
C18 C13 C24 C23 58.1(3) . . . . ?
O3 C21 C24 O7 55.1(2) . . . . ?
N3 C21 C24 O7 -123.16(16) . . . . ?
O3 C21 C24 C13 174.10(18) . . . . ?
N3 C21 C24 C13 -4.2(2) . . . . ?
O3 C21 C24 C23 -58.7(2) . . . . ?
N3 C21 C24 C23 122.97(17) . . . . ?
C11 C23 C24 O7 -160.06(10) . . . . ?
C26 C23 C24 O7 -35.22(13) . . . . ?
C19 C23 C24 O7 73.47(15) . . . . ?
C11 C23 C24 C13 72.73(17) . . . . ?
C26 C23 C24 C13 -162.43(14) . . . . ?
C19 C23 C24 C13 -53.7(2) . . . . ?
C11 C23 C24 C21 -45.11(17) . . . . ?
C26 C23 C24 C21 79.73(16) . . . . ?
C19 C23 C24 C21 -171.58(15) . . . . ?
C24 O7 C25 O6 175.64(14) . . . . ?
C24 O7 C25 C26 -3.54(14) . . . . ?
O6 C25 C26 C23 161.23(17) . . . . ?
O7 C25 C26 C23 -19.69(15) . . . . ?
C11 C23 C26 C25 154.65(14) . . . . ?
C19 C23 C26 C25 -78.71(17) . . . . ?
C24 C23 C26 C25 32.25(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        66.21
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.056
