# Electronic Supplementary Material (ESI) for Green Chemistry
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
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#  except for the purpose of generating routine backup copies 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 890741'
#TrackingRef '12449_web_deposit_cif_file_0_Shengjiao-Yan_1341559074.Sheng-Jiao Yan 1.cif'




_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

(2S,3'S,5R,6S)-ethyl 8-benzoyl-5-hydroxy-2-methyl-2'-oxo-5-(trifluoromethyl)-
2,3,5,6-tetrahydro-1H-spiro[imidazo[1,2-a]pyridine-7,3'-indoline]-6-carboxylate

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C26 H24 F3 N3 O5'

_chemical_formula_weight         515.48




_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'
F F 0.0171 0.0103 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P2(1)/c




_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   8.941(2)

_cell_length_b                   22.201(4)

_cell_length_c                   12.9747(17)

_cell_angle_alpha                90.00

_cell_angle_beta                 111.357(10)

_cell_angle_gamma                90.00

_cell_volume                     2398.6(8)

_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    1364

_cell_measurement_theta_min      2.42

_cell_measurement_theta_max      18.76



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.23

_exptl_crystal_size_mid          0.19

_exptl_crystal_size_min          0.14

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.427

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1072

_exptl_absorpt_coefficient_mu    0.115

_exptl_absorpt_correction_type   none

_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  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            16431

_diffrn_reflns_av_R_equivalents  0.0607

_diffrn_reflns_av_sigmaI/netI    0.0856

_diffrn_reflns_limit_h_min       -11

_diffrn_reflns_limit_h_max       11

_diffrn_reflns_limit_k_min       -20

_diffrn_reflns_limit_k_max       28

_diffrn_reflns_limit_l_min       -17

_diffrn_reflns_limit_l_max       17

_diffrn_reflns_theta_min         1.83

_diffrn_reflns_theta_max         28.26

_reflns_number_total             5607

_reflns_number_gt                2217

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F^2^, conventional R-factors R are based

on F, with F set to zero for negative F^2^. The threshold expression of

F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F^2^ 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/[\s^2^(Fo^2^)+(0.0840P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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       0.0048(12)

_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^

_refine_ls_number_reflns         5607

_refine_ls_number_parameters     358

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.1847

_refine_ls_R_factor_gt           0.0702

_refine_ls_wR_factor_ref         0.2182

_refine_ls_wR_factor_gt          0.1663

_refine_ls_goodness_of_fit_ref   1.041

_refine_ls_restrained_S_all      1.041

_refine_ls_shift/su_max          0.001

_refine_ls_shift/su_mean         0.000




_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 0.8272(4) 1.00814(14) 0.1369(2) 0.0512(8) Uani 1 1 d . . .
C2 C 0.7886(4) 1.06374(15) 0.1882(3) 0.0587(9) Uani 1 1 d . . .
C3 C 0.6432(5) 1.09375(17) 0.1377(3) 0.0753(11) Uani 1 1 d . . .
H3 H 0.5658 1.0777 0.0745 0.090 Uiso 1 1 calc R . .
C4 C 0.6137(6) 1.1471(2) 0.1809(4) 0.1015(15) Uani 1 1 d . . .
H4 H 0.5165 1.1669 0.1467 0.122 Uiso 1 1 calc R . .
C5 C 0.7265(7) 1.1711(2) 0.2738(5) 0.1099(17) Uani 1 1 d . . .
H5 H 0.7052 1.2070 0.3027 0.132 Uiso 1 1 calc R . .
C6 C 0.8704(6) 1.1426(2) 0.3247(4) 0.0943(14) Uani 1 1 d . . .
H6 H 0.9462 1.1590 0.3883 0.113 Uiso 1 1 calc R . .
C7 C 0.9032(5) 1.08896(18) 0.2809(3) 0.0759(11) Uani 1 1 d . . .
H7 H 1.0021 1.0702 0.3141 0.091 Uiso 1 1 calc R . .
C8 C 0.7878(3) 0.94923(14) 0.1643(2) 0.0494(8) Uani 1 1 d . . .
C9 C 0.8390(4) 0.89974(15) 0.1201(3) 0.0531(8) Uani 1 1 d . . .
C10 C 0.9454(5) 0.84145(16) 0.0138(3) 0.0734(10) Uani 1 1 d . . .
H10 H 0.8650 0.8355 -0.0606 0.088 Uiso 1 1 calc R . .
C11 C 1.1078(6) 0.83196(18) 0.0108(4) 0.1095(17) Uani 1 1 d . . .
H11A H 1.1239 0.8589 -0.0421 0.164 Uiso 1 1 calc R . .
H11B H 1.1176 0.7911 -0.0102 0.164 Uiso 1 1 calc R . .
H11C H 1.1872 0.8397 0.0827 0.164 Uiso 1 1 calc R . .
C12 C 0.9052(5) 0.80101(16) 0.0950(3) 0.0753(11) Uani 1 1 d . . .
H12A H 0.8440 0.7661 0.0579 0.090 Uiso 1 1 calc R . .
H12B H 1.0019 0.7876 0.1541 0.090 Uiso 1 1 calc R . .
C13 C 0.7778(4) 0.82497(16) 0.2374(3) 0.0649(10) Uani 1 1 d . . .
C14 C 0.7042(6) 0.7620(2) 0.2228(4) 0.0885(13) Uani 1 1 d . . .
C15 C 0.6594(5) 0.87172(17) 0.2483(3) 0.0675(10) Uani 1 1 d . . .
H15 H 0.5633 0.8684 0.1809 0.081 Uiso 1 1 calc R . .
C16 C 0.6054(7) 0.8589(2) 0.3442(4) 0.1088(18) Uani 1 1 d . A .
C17 C 0.4306(19) 0.8247(7) 0.4161(16) 0.114(6) Uani 0.50 1 d P A 2
H17A H 0.4659 0.7834 0.4336 0.137 Uiso 0.50 1 calc PR A 2
H17B H 0.4955 0.8502 0.4767 0.137 Uiso 0.50 1 calc PR A 2
C18 C 0.277(2) 0.8295(16) 0.404(2) 0.200(17) Uani 0.50 1 d P A 2
H18A H 0.2413 0.8700 0.3822 0.299 Uiso 0.50 1 calc PR A 2
H18B H 0.2650 0.8202 0.4725 0.299 Uiso 0.50 1 calc PR A 2
H18C H 0.2146 0.8020 0.3476 0.299 Uiso 0.50 1 calc PR A 2
C19 C 0.7172(4) 0.93822(14) 0.2533(2) 0.0539(9) Uani 1 1 d . . .
C20 C 0.8468(5) 0.95414(17) 0.3684(3) 0.0610(9) Uani 1 1 d . . .
C21 C 0.6229(4) 1.00918(18) 0.3519(3) 0.0690(10) Uani 1 1 d . . .
C22 C 0.5181(6) 1.0460(2) 0.3783(4) 0.0975(15) Uani 1 1 d . . .
H22 H 0.5501 1.0670 0.4448 0.117 Uiso 1 1 calc R . .
C23 C 0.3627(6) 1.0502(2) 0.3016(4) 0.1148(17) Uani 1 1 d . . .
H23 H 0.2895 1.0753 0.3162 0.138 Uiso 1 1 calc R . .
C24 C 0.3154(5) 1.0185(2) 0.2057(4) 0.0957(14) Uani 1 1 d . . .
H24 H 0.2099 1.0215 0.1565 0.115 Uiso 1 1 calc R . .
C25 C 0.4228(4) 0.98117(19) 0.1798(3) 0.0769(11) Uani 1 1 d . . .
H25 H 0.3895 0.9597 0.1137 0.092 Uiso 1 1 calc R . .
C26 C 0.5783(4) 0.97674(16) 0.2536(3) 0.0601(9) Uani 1 1 d . . .
C17' C 0.3042(14) 0.8659(5) 0.3528(8) 0.090(3) Uani 0.50 1 d P A 1
H17C H 0.3297 0.9009 0.4009 0.108 Uiso 0.50 1 calc PR A 1
H17D H 0.1987 0.8691 0.2951 0.108 Uiso 0.50 1 calc PR A 1
C18' C 0.335(3) 0.8105(13) 0.408(2) 0.175(14) Uani 0.50 1 d P A 1
H18D H 0.3117 0.7784 0.3551 0.263 Uiso 0.50 1 calc PR A 1
H18E H 0.2696 0.8065 0.4520 0.263 Uiso 0.50 1 calc PR A 1
H18F H 0.4466 0.8086 0.4555 0.263 Uiso 0.50 1 calc PR A 1
F1 F 0.5698(4) 0.75922(12) 0.1328(2) 0.1228(10) Uani 1 1 d . . .
F2 F 0.6630(3) 0.74682(11) 0.3080(2) 0.1194(10) Uani 1 1 d . . .
F3 F 0.8005(4) 0.71870(12) 0.2141(2) 0.1217(10) Uani 1 1 d . . .
N1 N 0.9231(4) 0.90089(12) 0.0544(2) 0.0663(8) Uani 1 1 d . . .
H1 H 0.9609 0.9334 0.0374 0.080 Uiso 1 1 calc R . .
N2 N 0.8089(3) 0.84041(12) 0.1377(2) 0.0623(8) Uani 1 1 d . . .
N3 N 0.7837(4) 0.99602(14) 0.4164(2) 0.0692(9) Uani 1 1 d . . .
H3A H 0.8358 1.0127 0.4791 0.083 Uiso 1 1 calc R . .
O1 O 0.8953(3) 1.01713(10) 0.06934(19) 0.0695(7) Uani 1 1 d . . .
O2 O 0.9188(3) 0.81884(11) 0.3309(2) 0.0915(9) Uani 1 1 d . . .
H2 H 0.9445 0.8517 0.3609 0.137 Uiso 1 1 calc R . .
O3 O 0.6870(6) 0.86611(17) 0.4388(3) 0.1598(19) Uani 1 1 d . . .
O4 O 0.4521(5) 0.84408(17) 0.3082(3) 0.1502(17) Uani 1 1 d . . .
O5 O 0.9849(3) 0.93550(11) 0.40561(18) 0.0736(7) Uani 1 1 d . . .




_atom_site_aniso_label

_atom_site_aniso_U_11

_atom_site_aniso_U_22

_atom_site_aniso_U_33

_atom_site_aniso_U_23

_atom_site_aniso_U_13

_atom_site_aniso_U_12







































C1 0.0442(19) 0.057(2) 0.0531(18) 0.0042(16) 0.0187(15) 0.0042(15)
C2 0.064(2) 0.058(2) 0.064(2) 0.0031(17) 0.0344(18) 0.0009(18)
C3 0.080(3) 0.070(3) 0.089(3) 0.001(2) 0.046(2) 0.012(2)
C4 0.113(4) 0.082(3) 0.133(4) 0.005(3) 0.073(3) 0.029(3)
C5 0.146(5) 0.077(4) 0.139(5) -0.020(3) 0.090(4) 0.000(3)
C6 0.123(4) 0.080(3) 0.094(3) -0.025(3) 0.056(3) -0.028(3)
C7 0.077(3) 0.075(3) 0.085(3) -0.007(2) 0.040(2) -0.012(2)
C8 0.0461(18) 0.058(2) 0.0464(17) -0.0007(15) 0.0195(14) -0.0063(15)
C9 0.053(2) 0.052(2) 0.0560(19) 0.0064(16) 0.0219(16) -0.0025(16)
C10 0.097(3) 0.057(2) 0.082(2) 0.0021(19) 0.051(2) 0.005(2)
C11 0.136(4) 0.066(3) 0.175(5) 0.019(3) 0.115(4) 0.018(3)
C12 0.090(3) 0.060(2) 0.089(3) -0.001(2) 0.048(2) -0.005(2)
C13 0.073(3) 0.062(2) 0.061(2) 0.0056(17) 0.025(2) -0.0228(19)
C14 0.116(4) 0.079(3) 0.074(3) -0.005(2) 0.038(3) -0.040(3)
C15 0.076(3) 0.077(3) 0.054(2) -0.0095(17) 0.0288(18) -0.032(2)
C16 0.181(5) 0.095(3) 0.087(3) -0.042(3) 0.091(3) -0.079(3)
C17 0.143(14) 0.096(8) 0.165(13) -0.036(9) 0.129(12) -0.046(8)
C18 0.111(14) 0.36(4) 0.164(17) -0.11(2) 0.097(13) -0.14(2)
C19 0.057(2) 0.065(2) 0.0401(17) -0.0057(15) 0.0172(15) -0.0196(17)
C20 0.068(2) 0.066(3) 0.0451(19) -0.0004(17) 0.0159(18) -0.020(2)
C21 0.064(2) 0.094(3) 0.056(2) -0.0179(19) 0.0300(19) -0.021(2)
C22 0.092(3) 0.128(4) 0.090(3) -0.042(3) 0.053(3) -0.026(3)
C23 0.074(3) 0.161(5) 0.124(4) -0.043(4) 0.053(3) -0.016(3)
C24 0.060(3) 0.128(4) 0.101(3) -0.023(3) 0.031(2) -0.013(3)
C25 0.058(2) 0.111(3) 0.065(2) -0.017(2) 0.026(2) -0.020(2)
C26 0.054(2) 0.080(3) 0.0517(19) -0.0119(17) 0.0255(16) -0.0178(18)
C17' 0.060(6) 0.119(9) 0.080(6) 0.009(5) 0.014(5) -0.032(6)
C18' 0.22(3) 0.23(2) 0.116(13) 0.065(14) 0.107(18) 0.05(2)
F1 0.140(2) 0.112(2) 0.106(2) -0.0307(15) 0.0328(19) -0.0713(18)
F2 0.178(3) 0.0896(18) 0.1149(19) 0.0032(14) 0.0829(19) -0.0569(17)
F3 0.178(3) 0.0622(18) 0.150(2) 0.0023(15) 0.090(2) -0.0255(17)
N1 0.082(2) 0.0501(19) 0.084(2) 0.0041(15) 0.0511(17) 0.0019(15)
N2 0.076(2) 0.0540(19) 0.0641(17) -0.0020(14) 0.0336(16) -0.0085(15)
N3 0.071(2) 0.088(2) 0.0473(15) -0.0168(15) 0.0199(16) -0.0247(17)
O1 0.0881(18) 0.0590(15) 0.0850(16) 0.0129(12) 0.0595(15) 0.0087(13)
O2 0.107(2) 0.0773(19) 0.0701(17) 0.0106(14) 0.0077(16) -0.0186(16)
O3 0.285(5) 0.146(3) 0.079(2) -0.040(2) 0.102(3) -0.130(3)
O4 0.181(4) 0.160(3) 0.180(4) -0.086(3) 0.149(3) -0.110(3)
O5 0.0684(17) 0.0724(18) 0.0598(14) -0.0017(12) -0.0007(12) -0.0082(13)



_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.

;




_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 O1 1.252(4) . ?
C1 C8 1.433(4) . ?
C1 C2 1.501(4) . ?
C2 C7 1.383(5) . ?
C2 C3 1.394(5) . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.392(4) . ?
C8 C19 1.524(4) . ?
C9 N1 1.326(4) . ?
C9 N2 1.380(4) . ?
C10 N1 1.461(4) . ?
C10 C11 1.482(5) . ?
C10 C12 1.524(5) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N2 1.470(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O2 1.401(4) . ?
C13 N2 1.459(4) . ?
C13 C15 1.525(5) . ?
C13 C14 1.527(5) . ?
C14 F3 1.322(5) . ?
C14 F2 1.330(4) . ?
C14 F1 1.338(5) . ?
C15 C16 1.517(5) . ?
C15 C19 1.557(5) . ?
C15 H15 0.9800 . ?
C16 O3 1.189(5) . ?
C16 O4 1.318(6) . ?
C17 C18 1.32(3) . ?
C17 O4 1.542(16) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C26 1.509(5) . ?
C19 C20 1.561(4) . ?
C20 O5 1.223(4) . ?
C20 N3 1.352(4) . ?
C21 C22 1.378(5) . ?
C21 C26 1.391(4) . ?
C21 N3 1.405(4) . ?
C22 C23 1.386(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.357(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.398(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(4) . ?
C25 H25 0.9300 . ?
C17' C18' 1.40(3) . ?
C17' O4 1.696(14) . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?
C18' H18D 0.9600 . ?
C18' H18E 0.9600 . ?
C18' H18F 0.9600 . ?
N1 H1 0.8600 . ?
N3 H3A 0.8600 . ?
O2 H2 0.8200 . ?




_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 C1 C8 123.1(3) . . ?
O1 C1 C2 115.3(3) . . ?
C8 C1 C2 121.6(3) . . ?
C7 C2 C3 119.0(4) . . ?
C7 C2 C1 120.1(3) . . ?
C3 C2 C1 120.7(3) . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 119.8(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C6 120.0(4) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C1 118.1(3) . . ?
C9 C8 C19 118.4(3) . . ?
C1 C8 C19 122.8(3) . . ?
N1 C9 N2 108.4(3) . . ?
N1 C9 C8 126.8(3) . . ?
N2 C9 C8 124.8(3) . . ?
N1 C10 C11 113.7(3) . . ?
N1 C10 C12 100.6(3) . . ?
C11 C10 C12 114.5(3) . . ?
N1 C10 H10 109.2 . . ?
C11 C10 H10 109.2 . . ?
C12 C10 H10 109.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C10 103.2(3) . . ?
N2 C12 H12A 111.1 . . ?
C10 C12 H12A 111.1 . . ?
N2 C12 H12B 111.1 . . ?
C10 C12 H12B 111.1 . . ?
H12A C12 H12B 109.1 . . ?
O2 C13 N2 112.9(3) . . ?
O2 C13 C15 114.9(3) . . ?
N2 C13 C15 106.5(3) . . ?
O2 C13 C14 103.3(3) . . ?
N2 C13 C14 108.5(3) . . ?
C15 C13 C14 110.6(3) . . ?
F3 C14 F2 105.8(4) . . ?
F3 C14 F1 107.3(4) . . ?
F2 C14 F1 106.4(4) . . ?
F3 C14 C13 114.3(4) . . ?
F2 C14 C13 111.5(4) . . ?
F1 C14 C13 111.1(4) . . ?
C16 C15 C13 112.8(4) . . ?
C16 C15 C19 110.1(3) . . ?
C13 C15 C19 114.7(3) . . ?
C16 C15 H15 106.2 . . ?
C13 C15 H15 106.2 . . ?
C19 C15 H15 106.2 . . ?
O3 C16 O4 124.6(4) . . ?
O3 C16 C15 124.2(5) . . ?
O4 C16 C15 110.9(4) . . ?
C18 C17 O4 109(2) . . ?
C18 C17 H17A 109.8 . . ?
O4 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
O4 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C26 C19 C8 118.6(3) . . ?
C26 C19 C15 106.1(3) . . ?
C8 C19 C15 110.0(3) . . ?
C26 C19 C20 101.2(3) . . ?
C8 C19 C20 108.7(3) . . ?
C15 C19 C20 112.0(2) . . ?
O5 C20 N3 125.6(3) . . ?
O5 C20 C19 126.3(4) . . ?
N3 C20 C19 107.9(3) . . ?
C22 C21 C26 122.8(4) . . ?
C22 C21 N3 128.1(3) . . ?
C26 C21 N3 109.1(3) . . ?
C21 C22 C23 117.2(4) . . ?
C21 C22 H22 121.4 . . ?
C23 C22 H22 121.4 . . ?
C24 C23 C22 121.3(5) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 121.1(4) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C26 C25 C24 118.9(3) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C25 C26 C21 118.8(3) . . ?
C25 C26 C19 131.6(3) . . ?
C21 C26 C19 109.5(3) . . ?
C18' C17' O4 83.7(13) . . ?
C18' C17' H17C 114.7 . . ?
O4 C17' H17C 114.7 . . ?
C18' C17' H17D 114.7 . . ?
O4 C17' H17D 114.7 . . ?
H17C C17' H17D 111.8 . . ?
C9 N1 C10 113.5(3) . . ?
C9 N1 H1 123.3 . . ?
C10 N1 H1 123.3 . . ?
C9 N2 C13 118.9(3) . . ?
C9 N2 C12 109.2(3) . . ?
C13 N2 C12 121.4(3) . . ?
C20 N3 C21 112.1(3) . . ?
C20 N3 H3A 123.9 . . ?
C21 N3 H3A 123.9 . . ?
C13 O2 H2 109.5 . . ?
C16 O4 C17 101.8(7) . . ?
C16 O4 C17' 130.3(4) . . ?
C17 O4 C17' 53.0(7) . . ?




_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag








































































































O1 C1 C2 C7 -85.2(4) . . . . ?
C8 C1 C2 C7 94.8(4) . . . . ?
O1 C1 C2 C3 88.8(4) . . . . ?
C8 C1 C2 C3 -91.1(4) . . . . ?
C7 C2 C3 C4 -1.1(5) . . . . ?
C1 C2 C3 C4 -175.2(4) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
C4 C5 C6 C7 0.6(7) . . . . ?
C3 C2 C7 C6 2.1(5) . . . . ?
C1 C2 C7 C6 176.3(3) . . . . ?
C5 C6 C7 C2 -1.9(6) . . . . ?
O1 C1 C8 C9 5.1(4) . . . . ?
C2 C1 C8 C9 -174.9(3) . . . . ?
O1 C1 C8 C19 174.9(3) . . . . ?
C2 C1 C8 C19 -5.1(4) . . . . ?
C1 C8 C9 N1 0.5(5) . . . . ?
C19 C8 C9 N1 -169.8(3) . . . . ?
C1 C8 C9 N2 -179.2(3) . . . . ?
C19 C8 C9 N2 10.5(4) . . . . ?
N1 C10 C12 N2 21.4(4) . . . . ?
C11 C10 C12 N2 143.7(3) . . . . ?
O2 C13 C14 F3 -55.7(4) . . . . ?
N2 C13 C14 F3 64.3(4) . . . . ?
C15 C13 C14 F3 -179.2(3) . . . . ?
O2 C13 C14 F2 64.2(5) . . . . ?
N2 C13 C14 F2 -175.8(4) . . . . ?
C15 C13 C14 F2 -59.3(5) . . . . ?
O2 C13 C14 F1 -177.4(4) . . . . ?
N2 C13 C14 F1 -57.3(5) . . . . ?
C15 C13 C14 F1 59.2(4) . . . . ?
O2 C13 C15 C16 -58.5(4) . . . . ?
N2 C13 C15 C16 175.7(3) . . . . ?
C14 C13 C15 C16 58.0(4) . . . . ?
O2 C13 C15 C19 68.6(4) . . . . ?
N2 C13 C15 C19 -57.2(3) . . . . ?
C14 C13 C15 C19 -175.0(3) . . . . ?
C13 C15 C16 O3 73.5(6) . . . . ?
C19 C15 C16 O3 -56.0(7) . . . . ?
C13 C15 C16 O4 -112.3(5) . . . . ?
C19 C15 C16 O4 118.2(4) . . . . ?
C9 C8 C19 C26 -142.8(3) . . . . ?
C1 C8 C19 C26 47.4(4) . . . . ?
C9 C8 C19 C15 -20.5(4) . . . . ?
C1 C8 C19 C15 169.7(3) . . . . ?
C9 C8 C19 C20 102.5(3) . . . . ?
C1 C8 C19 C20 -67.4(4) . . . . ?
C16 C15 C19 C26 -56.5(4) . . . . ?
C13 C15 C19 C26 175.1(3) . . . . ?
C16 C15 C19 C8 174.1(4) . . . . ?
C13 C15 C19 C8 45.6(4) . . . . ?
C16 C15 C19 C20 53.1(5) . . . . ?
C13 C15 C19 C20 -75.4(4) . . . . ?
C26 C19 C20 O5 -177.3(3) . . . . ?
C8 C19 C20 O5 -51.6(4) . . . . ?
C15 C19 C20 O5 70.1(4) . . . . ?
C26 C19 C20 N3 -2.1(3) . . . . ?
C8 C19 C20 N3 123.5(3) . . . . ?
C15 C19 C20 N3 -114.7(3) . . . . ?
C26 C21 C22 C23 -0.5(6) . . . . ?
N3 C21 C22 C23 -178.0(4) . . . . ?
C21 C22 C23 C24 1.4(7) . . . . ?
C22 C23 C24 C25 -1.3(8) . . . . ?
C23 C24 C25 C26 0.3(7) . . . . ?
C24 C25 C26 C21 0.5(6) . . . . ?
C24 C25 C26 C19 175.6(4) . . . . ?
C22 C21 C26 C25 -0.5(6) . . . . ?
N3 C21 C26 C25 177.4(3) . . . . ?
C22 C21 C26 C19 -176.5(4) . . . . ?
N3 C21 C26 C19 1.4(4) . . . . ?
C8 C19 C26 C25 66.3(5) . . . . ?
C15 C19 C26 C25 -58.0(4) . . . . ?
C20 C19 C26 C25 -175.0(4) . . . . ?
C8 C19 C26 C21 -118.3(3) . . . . ?
C15 C19 C26 C21 117.4(3) . . . . ?
C20 C19 C26 C21 0.4(3) . . . . ?
N2 C9 N1 C10 5.1(4) . . . . ?
C8 C9 N1 C10 -174.7(3) . . . . ?
C11 C10 N1 C9 -140.1(3) . . . . ?
C12 C10 N1 C9 -17.2(4) . . . . ?
N1 C9 N2 C13 155.7(3) . . . . ?
C8 C9 N2 C13 -24.6(5) . . . . ?
N1 C9 N2 C12 10.4(4) . . . . ?
C8 C9 N2 C12 -169.9(3) . . . . ?
O2 C13 N2 C9 -81.5(4) . . . . ?
C15 C13 N2 C9 45.6(4) . . . . ?
C14 C13 N2 C9 164.7(3) . . . . ?
O2 C13 N2 C12 59.5(4) . . . . ?
C15 C13 N2 C12 -173.5(3) . . . . ?
C14 C13 N2 C12 -54.4(5) . . . . ?
C10 C12 N2 C9 -20.5(4) . . . . ?
C10 C12 N2 C13 -164.7(3) . . . . ?
O5 C20 N3 C21 178.3(3) . . . . ?
C19 C20 N3 C21 3.1(4) . . . . ?
C22 C21 N3 C20 174.8(4) . . . . ?
C26 C21 N3 C20 -2.9(4) . . . . ?
O3 C16 O4 C17 -13.4(9) . . . . ?
C15 C16 O4 C17 172.4(7) . . . . ?
O3 C16 O4 C17' 37.7(10) . . . . ?
C15 C16 O4 C17' -136.5(6) . . . . ?
C18 C17 O4 C16 157.2(16) . . . . ?
C18 C17 O4 C17' 25.1(17) . . . . ?
C18' C17' O4 C16 -99.2(13) . . . . ?
C18' C17' O4 C17 -26.8(16) . . . . ?




_geom_hbond_atom_site_label_D

_geom_hbond_atom_site_label_H

_geom_hbond_atom_site_label_A

_geom_hbond_distance_DH

_geom_hbond_distance_HA

_geom_hbond_distance_DA

_geom_hbond_angle_DHA

_geom_hbond_site_symmetry_A




C17 H17B O3 0.97 1.98 2.387(12) 102.7 .
C15 H15 F1 0.98 2.51 2.872(4) 101.7 .
O2 H2 O5 0.82 1.94 2.753(3) 169.6 .
N1 H1 O1 0.86 2.04 2.607(4) 123.1 .



_diffrn_measured_fraction_theta_max 0.946

_diffrn_reflns_theta_full        28.26

_diffrn_measured_fraction_theta_full 0.946

_refine_diff_density_max         0.339

_refine_diff_density_min         -0.353

_refine_diff_density_rms         0.044





data_1
_database_code_depnum_ccdc_archive 'CCDC 890742'
#TrackingRef '12450_web_deposit_cif_file_0_ShengjiaoYan_1341559333.Sheng-Jiao Yan 2.cif'



_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(2R,3'S,5R,6S)-ethyl 8-benzoyl-5-hydroxy-2-methyl-2'-oxo-5-(trifluoromethyl)-
2,3,5,6-tetrahydro-1H-spiro[imidazo[1,2-a]pyridine-7,3'-indoline]-6-carboxylate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 Cl3 F3 N3 O5'
_chemical_formula_weight         634.85

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.489(5)
_cell_length_b                   11.635(5)
_cell_length_c                   13.375(5)
_cell_angle_alpha                73.462(5)
_cell_angle_beta                 80.503(5)
_cell_angle_gamma                72.854(5)
_cell_volume                     1489.3(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    932
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      26.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9532
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10468
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_sigmaI/netI    0.1466
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         26.31
_reflns_number_total             6121
_reflns_number_gt                2095
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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       0.010(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         6121
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2712
_refine_ls_R_factor_gt           0.1239
_refine_ls_wR_factor_ref         0.4173
_refine_ls_wR_factor_gt          0.3167
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0924(8) 0.4183(7) 0.3355(6) 0.073(2) Uani 1 1 d . . .
C2 C 0.1968(8) 0.4589(6) 0.2489(5) 0.0599(18) Uani 1 1 d . . .
C3 C 0.1542(8) 0.5532(7) 0.1618(6) 0.0656(19) Uani 1 1 d . . .
H3 H 0.0631 0.5842 0.1535 0.079 Uiso 1 1 calc R . .
C4 C 0.2440(9) 0.6016(7) 0.0875(6) 0.074(2) Uani 1 1 d . . .
H4 H 0.2142 0.6654 0.0296 0.089 Uiso 1 1 calc R . .
C5 C 0.3764(10) 0.5553(9) 0.0994(7) 0.091(3) Uani 1 1 d . . .
H5 H 0.4377 0.5855 0.0476 0.109 Uiso 1 1 calc R . .
C6 C 0.4233(9) 0.4625(9) 0.1885(9) 0.098(3) Uani 1 1 d . . .
H6 H 0.5143 0.4327 0.1975 0.118 Uiso 1 1 calc R . .
C7 C 0.3314(9) 0.4180(8) 0.2610(7) 0.083(2) Uani 1 1 d . . .
H7 H 0.3606 0.3575 0.3209 0.100 Uiso 1 1 calc R . .
C8 C 0.0201(7) 0.3392(6) 0.3273(5) 0.0562(17) Uani 1 1 d . . .
C9 C -0.0923(8) 0.3276(7) 0.3988(5) 0.0654(19) Uani 1 1 d . . .
C10 C -0.2591(8) 0.3573(8) 0.5341(6) 0.076(2) Uani 1 1 d . . .
H10 H -0.3264 0.4337 0.5424 0.091 Uiso 1 1 calc R . .
C11 C -0.2261(10) 0.2705(9) 0.6391(6) 0.108(3) Uani 1 1 d . . .
H11A H -0.1599 0.1965 0.6295 0.162 Uiso 1 1 calc R . .
H11B H -0.3056 0.2492 0.6766 0.162 Uiso 1 1 calc R . .
H11C H -0.1917 0.3105 0.6783 0.162 Uiso 1 1 calc R . .
C12 C -0.3025(8) 0.3004(8) 0.4637(6) 0.083(2) Uani 1 1 d . . .
H12A H -0.3363 0.2299 0.5034 0.099 Uiso 1 1 calc R . .
H12B H -0.3715 0.3604 0.4216 0.099 Uiso 1 1 calc R . .
C13 C -0.1747(7) 0.2139(6) 0.3075(5) 0.0623(19) Uani 1 1 d . . .
C14 C -0.2392(10) 0.1049(8) 0.3428(7) 0.082(2) Uani 1 1 d . . .
C15 C -0.0271(7) 0.1698(6) 0.2681(5) 0.0532(16) Uani 1 1 d . . .
H15 H 0.0156 0.1058 0.3270 0.064 Uiso 1 1 calc R . .
C16 C -0.0044(7) 0.1080(7) 0.1796(6) 0.0655(19) Uani 1 1 d . . .
C17 C 0.0943(9) -0.0808(7) 0.1251(6) 0.082(2) Uani 1 1 d . . .
H17A H 0.1059 -0.1687 0.1577 0.098 Uiso 1 1 calc R . .
H17B H 0.0219 -0.0533 0.0800 0.098 Uiso 1 1 calc R . .
C18 C 0.2190(10) -0.0609(9) 0.0621(8) 0.118(3) Uani 1 1 d . . .
H18A H 0.2061 0.0256 0.0273 0.177 Uiso 1 1 calc R . .
H18B H 0.2420 -0.1088 0.0108 0.177 Uiso 1 1 calc R . .
H18C H 0.2901 -0.0866 0.1070 0.177 Uiso 1 1 calc R . .
C19 C 0.0485(7) 0.2711(6) 0.2409(5) 0.0536(17) Uani 1 1 d . . .
C20 C 0.0118(8) 0.3664(6) 0.1328(5) 0.0523(16) Uani 1 1 d . . .
C21 C 0.2295(8) 0.2647(7) 0.1088(6) 0.0654(19) Uani 1 1 d . . .
C22 C 0.3582(9) 0.2239(9) 0.0637(7) 0.087(2) Uani 1 1 d . . .
H22 H 0.3818 0.2577 -0.0064 0.105 Uiso 1 1 calc R . .
C23 C 0.4507(9) 0.1317(10) 0.1254(9) 0.104(3) Uani 1 1 d . . .
H23 H 0.5369 0.1034 0.0957 0.125 Uiso 1 1 calc R . .
C24 C 0.4181(9) 0.0802(9) 0.2308(8) 0.096(3) Uani 1 1 d . . .
H24 H 0.4821 0.0207 0.2721 0.115 Uiso 1 1 calc R . .
C25 C 0.2858(9) 0.1208(7) 0.2726(7) 0.079(2) Uani 1 1 d . . .
H25 H 0.2606 0.0840 0.3415 0.095 Uiso 1 1 calc R . .
C26 C 0.1948(7) 0.2120(6) 0.2149(5) 0.0557(17) Uani 1 1 d . . .
C27 C 0.7445(14) 0.6844(13) 0.315(2) 0.289(15) Uani 1 1 d . . .
H27 H 0.8189 0.6156 0.3445 0.347 Uiso 1 1 calc R . .
Cl1 Cl 0.6541(7) 0.7701(6) 0.4139(4) 0.259(3) Uani 1 1 d . . .
Cl2 Cl 0.6242(6) 0.6289(5) 0.2858(5) 0.256(3) Uani 1 1 d . . .
Cl3 Cl 0.7992(6) 0.7782(5) 0.2089(6) 0.307(4) Uani 1 1 d . . .
F1 F -0.3685(6) 0.1376(5) 0.3747(4) 0.1068(17) Uani 1 1 d . . .
F2 F -0.1783(6) 0.0168(5) 0.4219(4) 0.1112(18) Uani 1 1 d . . .
F3 F -0.2293(5) 0.0487(5) 0.2681(4) 0.1032(16) Uani 1 1 d . . .
N1 N -0.1375(6) 0.3860(6) 0.4740(4) 0.0769(19) Uani 1 1 d . . .
H1 H -0.0994 0.4359 0.4866 0.092 Uiso 1 1 calc R . .
N2 N -0.1782(6) 0.2606(5) 0.3974(4) 0.0653(16) Uani 1 1 d . . .
N3 N 0.1194(6) 0.3555(5) 0.0641(4) 0.0601(15) Uani 1 1 d . . .
H3A H 0.1209 0.3988 0.0002 0.072 Uiso 1 1 calc R . .
O1 O 0.0802(7) 0.4634(7) 0.4116(5) 0.132(3) Uani 1 1 d . . .
O2 O -0.2549(5) 0.3004(4) 0.2318(4) 0.0724(14) Uani 1 1 d . . .
H2 H -0.2771 0.2641 0.1960 0.109 Uiso 1 1 calc R . .
O3 O -0.0372(5) 0.1614(4) 0.0921(4) 0.0727(15) Uani 1 1 d . . .
O4 O 0.0601(5) -0.0109(4) 0.2065(4) 0.0715(15) Uani 1 1 d . . .
O5 O -0.0969(5) 0.4407(4) 0.1172(3) 0.0641(13) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.081(5) 0.093(6) 0.057(5) -0.040(4) 0.021(4) -0.034(4)
C2 0.071(5) 0.072(5) 0.044(4) -0.027(4) 0.007(4) -0.027(4)
C3 0.063(5) 0.077(5) 0.057(5) -0.027(4) -0.001(4) -0.013(4)
C4 0.087(6) 0.077(5) 0.060(5) -0.017(4) 0.008(5) -0.032(5)
C5 0.097(7) 0.103(7) 0.085(6) -0.041(6) 0.037(6) -0.052(6)
C6 0.058(5) 0.102(7) 0.130(9) -0.031(7) -0.005(6) -0.013(5)
C7 0.076(6) 0.094(6) 0.080(6) -0.014(5) -0.010(5) -0.029(5)
C8 0.065(5) 0.066(4) 0.043(4) -0.020(3) 0.001(3) -0.022(3)
C9 0.084(5) 0.072(5) 0.045(4) -0.017(4) 0.003(4) -0.031(4)
C10 0.082(6) 0.094(6) 0.056(5) -0.029(4) 0.019(4) -0.033(4)
C11 0.144(9) 0.118(7) 0.057(5) -0.007(5) -0.004(6) -0.045(6)
C12 0.080(6) 0.111(6) 0.070(5) -0.036(5) 0.023(5) -0.046(5)
C13 0.076(5) 0.069(4) 0.054(4) -0.021(4) -0.006(4) -0.031(4)
C14 0.096(7) 0.098(7) 0.073(6) -0.042(5) 0.015(5) -0.048(5)
C15 0.061(4) 0.060(4) 0.039(3) -0.015(3) -0.005(3) -0.014(3)
C16 0.067(5) 0.073(5) 0.061(5) -0.023(4) -0.006(4) -0.018(4)
C17 0.124(7) 0.068(5) 0.058(5) -0.032(4) 0.002(5) -0.022(5)
C18 0.132(9) 0.131(8) 0.110(8) -0.067(7) 0.033(7) -0.052(7)
C19 0.062(4) 0.060(4) 0.041(4) -0.018(3) -0.002(3) -0.017(3)
C20 0.070(5) 0.055(4) 0.033(3) -0.012(3) -0.003(4) -0.018(4)
C21 0.073(5) 0.078(5) 0.057(4) -0.038(4) 0.010(4) -0.027(4)
C22 0.073(6) 0.114(7) 0.079(6) -0.040(5) 0.024(5) -0.033(5)
C23 0.067(6) 0.121(8) 0.117(9) -0.040(7) 0.006(6) -0.011(6)
C24 0.070(6) 0.104(7) 0.102(8) -0.035(6) -0.011(6) 0.004(5)
C25 0.083(6) 0.079(5) 0.069(5) -0.023(4) -0.006(5) -0.010(4)
C26 0.060(4) 0.063(4) 0.047(4) -0.025(3) 0.004(4) -0.015(3)
C27 0.095(10) 0.115(11) 0.50(4) 0.095(16) 0.076(15) -0.015(8)
Cl1 0.297(7) 0.264(6) 0.187(5) 0.032(4) -0.037(5) -0.108(6)
Cl2 0.216(5) 0.205(5) 0.328(7) -0.013(5) -0.001(5) -0.093(4)
Cl3 0.234(5) 0.162(4) 0.470(11) -0.077(5) 0.159(6) -0.078(4)
F1 0.098(4) 0.144(4) 0.102(4) -0.045(3) 0.022(3) -0.071(3)
F2 0.145(5) 0.097(4) 0.090(4) 0.007(3) -0.007(3) -0.060(3)
F3 0.122(4) 0.121(4) 0.099(4) -0.060(3) 0.022(3) -0.066(3)
N1 0.096(5) 0.106(5) 0.050(4) -0.043(4) 0.025(3) -0.052(4)
N2 0.072(4) 0.084(4) 0.050(3) -0.026(3) 0.016(3) -0.037(3)
N3 0.068(4) 0.067(4) 0.038(3) -0.011(3) 0.004(3) -0.012(3)
O1 0.160(6) 0.204(7) 0.103(5) -0.117(5) 0.074(5) -0.126(6)
O2 0.065(3) 0.096(4) 0.057(3) -0.023(3) -0.006(3) -0.017(3)
O3 0.106(4) 0.071(3) 0.046(3) -0.017(2) -0.018(3) -0.021(3)
O4 0.098(4) 0.059(3) 0.052(3) -0.017(2) -0.012(3) -0.008(3)
O5 0.070(3) 0.067(3) 0.047(3) -0.004(2) -0.008(2) -0.013(3)

_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 O1 1.244(8) . ?
C1 C8 1.390(9) . ?
C1 C2 1.530(10) . ?
C2 C7 1.371(10) . ?
C2 C3 1.385(9) . ?
C3 C4 1.369(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.352(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.355(12) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.403(10) . ?
C8 C19 1.523(8) . ?
C9 N1 1.320(8) . ?
C9 N2 1.359(8) . ?
C10 N1 1.464(9) . ?
C10 C12 1.486(10) . ?
C10 C11 1.503(10) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N2 1.483(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O2 1.396(7) . ?
C13 N2 1.444(8) . ?
C13 C14 1.533(10) . ?
C13 C15 1.534(10) . ?
C14 F3 1.317(8) . ?
C14 F1 1.328(10) . ?
C14 F2 1.341(9) . ?
C15 C16 1.506(9) . ?
C15 C19 1.537(9) . ?
C15 H15 0.9800 . ?
C16 O3 1.210(8) . ?
C16 O4 1.321(8) . ?
C17 C18 1.476(12) . ?
C17 O4 1.477(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C26 1.512(9) . ?
C19 C20 1.577(9) . ?
C20 O5 1.219(7) . ?
C20 N3 1.332(8) . ?
C21 C22 1.389(11) . ?
C21 N3 1.399(8) . ?
C21 C26 1.410(9) . ?
C22 C23 1.385(12) . ?
C22 H22 0.9300 . ?
C23 C24 1.394(13) . ?
C23 H23 0.9300 . ?
C24 C25 1.403(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.346(9) . ?
C25 H25 0.9300 . ?
C27 Cl3 1.658(17) . ?
C27 Cl2 1.72(2) . ?
C27 Cl1 1.85(2) . ?
C27 H27 0.9800 . ?
N1 H1 0.8600 . ?
N3 H3A 0.8600 . ?
O2 H2 0.8200 . ?

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 C1 C8 124.9(7) . . ?
O1 C1 C2 113.1(6) . . ?
C8 C1 C2 122.0(6) . . ?
C7 C2 C3 118.2(7) . . ?
C7 C2 C1 122.1(7) . . ?
C3 C2 C1 119.0(7) . . ?
C4 C3 C2 121.1(7) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 119.2(8) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.3(8) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 117.8(8) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C2 122.3(8) . . ?
C6 C7 H7 118.9 . . ?
C2 C7 H7 118.9 . . ?
C1 C8 C9 118.1(6) . . ?
C1 C8 C19 124.3(6) . . ?
C9 C8 C19 117.4(6) . . ?
N1 C9 N2 108.5(6) . . ?
N1 C9 C8 126.0(7) . . ?
N2 C9 C8 125.4(6) . . ?
N1 C10 C12 101.0(6) . . ?
N1 C10 C11 110.1(7) . . ?
C12 C10 C11 113.7(7) . . ?
N1 C10 H10 110.6 . . ?
C12 C10 H10 110.6 . . ?
C11 C10 H10 110.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C10 103.4(6) . . ?
N2 C12 H12A 111.1 . . ?
C10 C12 H12A 111.1 . . ?
N2 C12 H12B 111.1 . . ?
C10 C12 H12B 111.1 . . ?
H12A C12 H12B 109.0 . . ?
O2 C13 N2 112.1(6) . . ?
O2 C13 C14 104.2(6) . . ?
N2 C13 C14 108.2(6) . . ?
O2 C13 C15 114.5(6) . . ?
N2 C13 C15 107.3(5) . . ?
C14 C13 C15 110.5(6) . . ?
F3 C14 F1 106.6(7) . . ?
F3 C14 F2 105.4(7) . . ?
F1 C14 F2 107.1(7) . . ?
F3 C14 C13 112.5(7) . . ?
F1 C14 C13 113.5(7) . . ?
F2 C14 C13 111.2(7) . . ?
C16 C15 C13 114.4(5) . . ?
C16 C15 C19 110.4(5) . . ?
C13 C15 C19 113.7(5) . . ?
C16 C15 H15 105.9 . . ?
C13 C15 H15 105.9 . . ?
C19 C15 H15 105.9 . . ?
O3 C16 O4 123.3(7) . . ?
O3 C16 C15 124.1(7) . . ?
O4 C16 C15 112.5(6) . . ?
C18 C17 O4 110.1(7) . . ?
C18 C17 H17A 109.6 . . ?
O4 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
O4 C17 H17B 109.6 . . ?
H17A C17 H17B 108.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C26 C19 C8 115.2(5) . . ?
C26 C19 C15 108.1(5) . . ?
C8 C19 C15 110.8(5) . . ?
C26 C19 C20 100.7(6) . . ?
C8 C19 C20 110.2(5) . . ?
C15 C19 C20 111.4(5) . . ?
O5 C20 N3 126.2(6) . . ?
O5 C20 C19 124.6(6) . . ?
N3 C20 C19 109.1(6) . . ?
C22 C21 N3 129.5(7) . . ?
C22 C21 C26 120.2(8) . . ?
N3 C21 C26 110.3(6) . . ?
C23 C22 C21 118.4(8) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
C22 C23 C24 121.9(9) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C23 C24 C25 117.9(8) . . ?
C23 C24 H24 121.0 . . ?
C25 C24 H24 121.0 . . ?
C26 C25 C24 121.3(8) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C21 120.1(7) . . ?
C25 C26 C19 131.5(7) . . ?
C21 C26 C19 108.3(6) . . ?
Cl3 C27 Cl2 110.5(16) . . ?
Cl3 C27 Cl1 111.3(10) . . ?
Cl2 C27 Cl1 103.2(7) . . ?
Cl3 C27 H27 110.6 . . ?
Cl2 C27 H27 110.6 . . ?
Cl1 C27 H27 110.6 . . ?
C9 N1 C10 113.3(6) . . ?
C9 N1 H1 123.4 . . ?
C10 N1 H1 123.4 . . ?
C9 N2 C13 120.5(6) . . ?
C9 N2 C12 108.7(6) . . ?
C13 N2 C12 123.5(6) . . ?
C20 N3 C21 111.5(6) . . ?
C20 N3 H3A 124.2 . . ?
C21 N3 H3A 124.2 . . ?
C13 O2 H2 109.5 . . ?
C16 O4 C17 117.8(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 70.4(10) . . . . ?
C8 C1 C2 C7 -109.7(9) . . . . ?
O1 C1 C2 C3 -100.1(9) . . . . ?
C8 C1 C2 C3 79.8(9) . . . . ?
C7 C2 C3 C4 2.3(10) . . . . ?
C1 C2 C3 C4 173.1(6) . . . . ?
C2 C3 C4 C5 0.6(11) . . . . ?
C3 C4 C5 C6 -2.8(12) . . . . ?
C4 C5 C6 C7 2.0(13) . . . . ?
C5 C6 C7 C2 1.0(13) . . . . ?
C3 C2 C7 C6 -3.1(12) . . . . ?
C1 C2 C7 C6 -173.7(8) . . . . ?
O1 C1 C8 C9 13.1(12) . . . . ?
C2 C1 C8 C9 -166.7(7) . . . . ?
O1 C1 C8 C19 -171.5(8) . . . . ?
C2 C1 C8 C19 8.6(11) . . . . ?
C1 C8 C9 N1 0.5(11) . . . . ?
C19 C8 C9 N1 -175.2(6) . . . . ?
C1 C8 C9 N2 175.6(7) . . . . ?
C19 C8 C9 N2 0.0(10) . . . . ?
N1 C10 C12 N2 21.1(8) . . . . ?
C11 C10 C12 N2 -96.8(8) . . . . ?
O2 C13 C14 F3 66.6(9) . . . . ?
N2 C13 C14 F3 -174.0(7) . . . . ?
C15 C13 C14 F3 -56.8(9) . . . . ?
O2 C13 C14 F1 -54.6(8) . . . . ?
N2 C13 C14 F1 64.8(9) . . . . ?
C15 C13 C14 F1 -178.0(6) . . . . ?
O2 C13 C14 F2 -175.5(6) . . . . ?
N2 C13 C14 F2 -56.1(9) . . . . ?
C15 C13 C14 F2 61.2(8) . . . . ?
O2 C13 C15 C16 -59.8(7) . . . . ?
N2 C13 C15 C16 175.1(5) . . . . ?
C14 C13 C15 C16 57.4(8) . . . . ?
O2 C13 C15 C19 68.2(7) . . . . ?
N2 C13 C15 C19 -56.8(7) . . . . ?
C14 C13 C15 C19 -174.6(6) . . . . ?
C13 C15 C16 O3 68.1(9) . . . . ?
C19 C15 C16 O3 -61.6(9) . . . . ?
C13 C15 C16 O4 -114.2(7) . . . . ?
C19 C15 C16 O4 116.0(6) . . . . ?
C1 C8 C19 C26 44.0(9) . . . . ?
C9 C8 C19 C26 -140.7(6) . . . . ?
C1 C8 C19 C15 167.1(6) . . . . ?
C9 C8 C19 C15 -17.5(8) . . . . ?
C1 C8 C19 C20 -69.1(9) . . . . ?
C9 C8 C19 C20 106.3(7) . . . . ?
C16 C15 C19 C26 -56.0(7) . . . . ?
C13 C15 C19 C26 173.9(5) . . . . ?
C16 C15 C19 C8 176.9(6) . . . . ?
C13 C15 C19 C8 46.8(7) . . . . ?
C16 C15 C19 C20 53.7(7) . . . . ?
C13 C15 C19 C20 -76.4(7) . . . . ?
C26 C19 C20 O5 -176.4(6) . . . . ?
C8 C19 C20 O5 -54.3(8) . . . . ?
C15 C19 C20 O5 69.2(8) . . . . ?
C26 C19 C20 N3 1.1(6) . . . . ?
C8 C19 C20 N3 123.1(6) . . . . ?
C15 C19 C20 N3 -113.4(6) . . . . ?
N3 C21 C22 C23 179.9(7) . . . . ?
C26 C21 C22 C23 -0.5(12) . . . . ?
C21 C22 C23 C24 -0.4(14) . . . . ?
C22 C23 C24 C25 2.6(15) . . . . ?
C23 C24 C25 C26 -4.0(13) . . . . ?
C24 C25 C26 C21 3.1(11) . . . . ?
C24 C25 C26 C19 179.7(7) . . . . ?
C22 C21 C26 C25 -0.8(10) . . . . ?
N3 C21 C26 C25 178.8(6) . . . . ?
C22 C21 C26 C19 -178.1(6) . . . . ?
N3 C21 C26 C19 1.5(7) . . . . ?
C8 C19 C26 C25 63.1(9) . . . . ?
C15 C19 C26 C25 -61.5(9) . . . . ?
C20 C19 C26 C25 -178.4(7) . . . . ?
C8 C19 C26 C21 -120.0(6) . . . . ?
C15 C19 C26 C21 115.4(6) . . . . ?
C20 C19 C26 C21 -1.5(6) . . . . ?
N2 C9 N1 C10 2.5(9) . . . . ?
C8 C9 N1 C10 178.4(7) . . . . ?
C12 C10 N1 C9 -15.7(9) . . . . ?
C11 C10 N1 C9 104.7(8) . . . . ?
N1 C9 N2 C13 163.6(6) . . . . ?
C8 C9 N2 C13 -12.3(11) . . . . ?
N1 C9 N2 C12 12.3(8) . . . . ?
C8 C9 N2 C12 -163.6(7) . . . . ?
O2 C13 N2 C9 -87.3(8) . . . . ?
C14 C13 N2 C9 158.4(7) . . . . ?
C15 C13 N2 C9 39.2(8) . . . . ?
O2 C13 N2 C12 59.7(8) . . . . ?
C14 C13 N2 C12 -54.6(9) . . . . ?
C15 C13 N2 C12 -173.8(6) . . . . ?
C10 C12 N2 C9 -21.6(8) . . . . ?
C10 C12 N2 C13 -171.9(6) . . . . ?
O5 C20 N3 C21 177.1(6) . . . . ?
C19 C20 N3 C21 -0.2(7) . . . . ?
C22 C21 N3 C20 178.7(7) . . . . ?
C26 C21 N3 C20 -0.8(7) . . . . ?
O3 C16 O4 C17 0.5(11) . . . . ?
C15 C16 O4 C17 -177.2(6) . . . . ?
C18 C17 O4 C16 82.9(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15 F2 0.98 2.54 2.902(8) 101.6 .
C12 H12A F1 0.97 2.39 2.795(9) 104.8 .
C6 H6 O2 0.93 2.49 3.400(10) 165.4 1_655
N3 H3A O5 0.86 2.05 2.853(7) 155.4 2_565
O2 H2 F3 0.82 2.35 2.767(7) 112.6 .
N1 H1 O1 0.86 2.10 2.867(8) 148.4 2_566
N1 H1 O1 0.86 2.05 2.623(8) 123.2 .

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        26.31
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.082