# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013


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#  This CIF contains data from an original supplementary publication 
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#  experimental, refinement, atomic coordinates, 
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data_am97m
_database_code_depnum_ccdc_archive 'CCDC 902322'
#TrackingRef 'web_deposit_cif_file_0_B.Sridhar_1348129929.am97mF.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
5-(5-oxo-5,6,7,8-tetrahydroquinolin-2-yl)thiophen-2-yl acetate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N O3 S'
_chemical_formula_sum            'C15 H13 N O3 S'
_chemical_formula_weight         287.32
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_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                   12.5933(11)
_cell_length_b                   15.1264(13)
_cell_length_c                   15.0649(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.798(1)
_cell_angle_gamma                90.00
_cell_volume                     2664.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9172
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.92
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.249
_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      294(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_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24988
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4682
_reflns_number_gt                3740
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_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^)+(0.0793P)^2^+1.3249P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4682
_refine_ls_number_parameters     358
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1740
_refine_ls_wR_factor_gt          0.1625
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.193
_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
C1A C 0.5363(2) 0.71969(16) 0.37749(17) 0.0411(6) Uani 1 1 d . B .
C2A C 0.4030(2) 0.82521(16) 0.37509(18) 0.0444(6) Uani 1 1 d . B .
C3A C 0.2851(2) 0.84467(19) 0.3736(3) 0.0656(7) Uani 1 1 d D . .
H3A H 0.2332 0.7989 0.3372 0.079 Uiso 1 1 calc R A 1
H3B H 0.2870 0.8424 0.4385 0.079 Uiso 1 1 calc R A 1
C4A C 0.2407(5) 0.9308(3) 0.3323(6) 0.0656(7) Uani 0.576(6) 1 d PD B 1
H4A H 0.1729 0.9438 0.3459 0.079 Uiso 0.576(6) 1 calc PR B 1
H4B H 0.2178 0.9270 0.2634 0.079 Uiso 0.576(6) 1 calc PR B 1
C4A' C 0.2696(7) 0.9371(4) 0.3990(8) 0.0656(7) Uani 0.424(6) 1 d PD B 2
H4A' H 0.1882 0.9493 0.3739 0.079 Uiso 0.424(6) 1 calc PR B 2
H4B' H 0.2953 0.9403 0.4681 0.079 Uiso 0.424(6) 1 calc PR B 2
C5A C 0.3246(3) 1.00704(19) 0.3684(3) 0.0676(8) Uani 1 1 d D . .
H5A H 0.2962 1.0569 0.3257 0.081 Uiso 1 1 calc R B 1
H5B H 0.3262 1.0246 0.4308 0.081 Uiso 1 1 calc R B 1
C6A C 0.4441(2) 0.98779(17) 0.3764(2) 0.0528(7) Uani 1 1 d . B .
C7A C 0.4770(2) 0.89350(16) 0.37622(18) 0.0439(6) Uani 1 1 d . . .
C8A C 0.5852(2) 0.87161(17) 0.3785(2) 0.0526(7) Uani 1 1 d . B .
H8A H 0.6369 0.9159 0.3797 0.063 Uiso 1 1 calc R . .
C9A C 0.6153(2) 0.78472(16) 0.3790(2) 0.0507(7) Uani 1 1 d . . .
H9A H 0.6874 0.7693 0.3803 0.061 Uiso 1 1 calc R B .
C10A C 0.5635(2) 0.62601(16) 0.37730(18) 0.0428(6) Uani 1 1 d . . .
C11A C 0.6639(2) 0.58852(18) 0.3816(2) 0.0525(7) Uani 1 1 d . B .
H11A H 0.7277 0.6213 0.3849 0.063 Uiso 1 1 calc R . .
C12A C 0.6614(2) 0.49585(17) 0.3806(2) 0.0527(7) Uani 1 1 d . . .
H12A H 0.7229 0.4604 0.3835 0.063 Uiso 1 1 calc R B .
C13A C 0.5592(2) 0.46456(16) 0.37487(19) 0.0457(6) Uani 1 1 d . B .
C14A C 0.4356(3) 0.34132(18) 0.3603(2) 0.0554(7) Uani 1 1 d . B .
C15A C 0.4385(3) 0.24358(19) 0.3670(2) 0.0675(9) Uani 1 1 d . . .
H15A H 0.4421 0.2260 0.4293 0.101 Uiso 1 1 calc R . .
H15B H 0.5045 0.2217 0.3567 0.101 Uiso 1 1 calc R . .
H15C H 0.3706 0.2196 0.3194 0.101 Uiso 1 1 calc R . .
N1A N 0.43103(18) 0.73961(13) 0.37558(16) 0.0460(5) Uani 1 1 d . . .
O1A O 0.5125(2) 1.04590(12) 0.38424(19) 0.0745(7) Uani 1 1 d . . .
O2A O 0.54058(16) 0.37476(11) 0.37658(15) 0.0561(5) Uani 1 1 d . . .
O3A O 0.35402(19) 0.38697(14) 0.3422(2) 0.0882(8) Uani 1 1 d . . .
S1A S 0.46218(6) 0.54660(4) 0.37037(5) 0.0500(2) Uani 1 1 d . B .
C1B C -0.0421(2) 0.62523(16) 0.60943(17) 0.0421(6) Uani 1 1 d . B .
C2B C 0.0895(2) 0.73260(16) 0.61251(18) 0.0437(6) Uani 1 1 d . B .
C3B C 0.2079(2) 0.75404(18) 0.6168(3) 0.0671(8) Uani 1 1 d D . .
H3C H 0.2621 0.7195 0.6679 0.081 Uiso 1 1 calc R B 1
H3D H 0.2140 0.7351 0.5574 0.081 Uiso 1 1 calc R B 1
C4B C 0.2408(6) 0.8448(4) 0.6319(6) 0.0671(8) Uani 0.576(6) 1 d PD B 1
H4C H 0.2918 0.8499 0.6983 0.081 Uiso 0.576(6) 1 calc PR B 1
H4D H 0.2866 0.8565 0.5938 0.081 Uiso 0.576(6) 1 calc PR B 1
C4B' C 0.2477(8) 0.8419(6) 0.6694(7) 0.0671(8) Uani 0.424(6) 1 d PD B 2
H4C' H 0.3238 0.8563 0.6718 0.081 Uiso 0.424(6) 1 calc PR B 2
H4D' H 0.2503 0.8374 0.7344 0.081 Uiso 0.424(6) 1 calc PR B 2
C5B C 0.1615(3) 0.9154(2) 0.6143(3) 0.0761(10) Uani 1 1 d D . .
H5C H 0.1569 0.9439 0.5554 0.091 Uiso 1 1 calc R B 1
H5D H 0.1929 0.9583 0.6652 0.091 Uiso 1 1 calc R B 1
C6B C 0.0419(2) 0.89470(18) 0.6066(2) 0.0568(7) Uani 1 1 d . B .
C7B C 0.0116(2) 0.79974(16) 0.60641(19) 0.0461(6) Uani 1 1 d . . .
C8B C -0.0986(2) 0.77628(17) 0.5989(2) 0.0540(7) Uani 1 1 d . B .
H8B H -0.1529 0.8198 0.5932 0.065 Uiso 1 1 calc R . .
C9B C -0.1260(2) 0.68914(17) 0.6002(2) 0.0531(7) Uani 1 1 d . . .
H9B H -0.1992 0.6725 0.5949 0.064 Uiso 1 1 calc R B .
C10B C -0.0660(2) 0.53143(16) 0.61498(18) 0.0445(6) Uani 1 1 d . . .
C11B C -0.1660(2) 0.49287(17) 0.6104(2) 0.0535(7) Uani 1 1 d . B .
H11B H -0.2319 0.5248 0.6028 0.064 Uiso 1 1 calc R . .
C12B C -0.1598(2) 0.40058(18) 0.6183(2) 0.0550(7) Uani 1 1 d . . .
H12B H -0.2206 0.3645 0.6158 0.066 Uiso 1 1 calc R B .
C13B C -0.0546(2) 0.37065(16) 0.63014(19) 0.0459(6) Uani 1 1 d . B .
C14B C 0.0755(3) 0.24949(18) 0.6596(2) 0.0544(7) Uani 1 1 d . B .
C15B C 0.0773(3) 0.15138(18) 0.6581(2) 0.0664(8) Uani 1 1 d . . .
H15D H 0.0695 0.1314 0.5955 0.100 Uiso 1 1 calc R . .
H15E H 0.0150 0.1288 0.6736 0.100 Uiso 1 1 calc R . .
H15F H 0.1484 0.1305 0.7041 0.100 Uiso 1 1 calc R . .
N1B N 0.06360(18) 0.64684(13) 0.61466(16) 0.0455(5) Uani 1 1 d . . .
O1B O -0.0275(2) 0.95198(13) 0.5984(2) 0.0841(8) Uani 1 1 d . . .
O2B O -0.03186(15) 0.28099(11) 0.63583(15) 0.0549(5) Uani 1 1 d . . .
O3B O 0.15619(19) 0.29643(14) 0.6802(2) 0.0915(9) Uani 1 1 d . . .
S1B S 0.03973(5) 0.45348(4) 0.63125(5) 0.0485(2) Uani 1 1 d . B .
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
C1A 0.0387(13) 0.0361(13) 0.0490(14) -0.0015(10) 0.0169(11) -0.0010(10)
C2A 0.0407(13) 0.0374(13) 0.0551(15) -0.0023(11) 0.0180(11) 0.0013(10)
C3A 0.0500(14) 0.0469(13) 0.107(2) -0.0065(14) 0.0373(15) 0.0043(10)
C4A 0.0500(14) 0.0469(13) 0.107(2) -0.0065(14) 0.0373(15) 0.0043(10)
C4A' 0.0500(14) 0.0469(13) 0.107(2) -0.0065(14) 0.0373(15) 0.0043(10)
C5A 0.0623(18) 0.0417(16) 0.097(2) -0.0025(15) 0.0274(17) 0.0108(13)
C6A 0.0548(16) 0.0358(14) 0.0652(17) -0.0002(12) 0.0193(13) 0.0012(12)
C7A 0.0456(14) 0.0337(13) 0.0512(14) -0.0020(10) 0.0166(11) -0.0001(10)
C8A 0.0492(15) 0.0370(14) 0.0760(19) -0.0050(12) 0.0283(14) -0.0073(11)
C9A 0.0429(14) 0.0396(14) 0.0749(18) -0.0038(12) 0.0281(13) -0.0007(11)
C10A 0.0402(13) 0.0335(13) 0.0566(15) -0.0007(11) 0.0201(11) -0.0004(10)
C11A 0.0413(14) 0.0415(14) 0.0776(18) -0.0027(13) 0.0256(13) -0.0019(11)
C12A 0.0422(14) 0.0392(14) 0.0790(19) -0.0014(12) 0.0253(13) 0.0058(11)
C13A 0.0435(14) 0.0343(13) 0.0601(16) 0.0018(11) 0.0200(12) 0.0046(10)
C14A 0.0599(17) 0.0367(14) 0.080(2) -0.0032(13) 0.0375(15) -0.0030(13)
C15A 0.080(2) 0.0388(16) 0.088(2) 0.0017(14) 0.0359(18) -0.0056(14)
N1A 0.0427(12) 0.0312(11) 0.0661(14) -0.0019(9) 0.0227(10) -0.0001(9)
O1A 0.0685(14) 0.0329(11) 0.122(2) -0.0021(11) 0.0351(13) -0.0057(10)
O2A 0.0503(11) 0.0293(9) 0.0900(14) 0.0040(9) 0.0276(10) 0.0044(8)
O3A 0.0588(13) 0.0457(12) 0.175(3) -0.0101(14) 0.0602(15) -0.0033(10)
S1A 0.0407(4) 0.0324(4) 0.0820(5) 0.0030(3) 0.0286(4) 0.0028(2)
C1B 0.0418(14) 0.0346(13) 0.0509(14) 0.0008(10) 0.0182(11) -0.0002(10)
C2B 0.0429(13) 0.0355(13) 0.0529(15) 0.0012(10) 0.0179(11) -0.0020(10)
C3B 0.0561(13) 0.0456(12) 0.107(2) -0.0021(15) 0.0389(16) -0.0077(10)
C4B 0.0561(13) 0.0456(12) 0.107(2) -0.0021(15) 0.0389(16) -0.0077(10)
C4B' 0.0561(13) 0.0456(12) 0.107(2) -0.0021(15) 0.0389(16) -0.0077(10)
C5B 0.065(2) 0.0417(16) 0.119(3) 0.0108(17) 0.0306(19) -0.0095(14)
C6B 0.0599(17) 0.0361(15) 0.0758(19) 0.0036(13) 0.0270(15) 0.0024(13)
C7B 0.0499(15) 0.0347(13) 0.0541(15) 0.0025(11) 0.0196(12) 0.0004(11)
C8B 0.0491(15) 0.0392(14) 0.0773(19) 0.0056(13) 0.0278(14) 0.0084(12)
C9B 0.0417(14) 0.0440(15) 0.0774(19) 0.0041(13) 0.0266(13) 0.0006(11)
C10B 0.0402(14) 0.0388(13) 0.0567(15) -0.0006(11) 0.0206(11) -0.0010(11)
C11B 0.0449(15) 0.0400(14) 0.0808(19) -0.0003(13) 0.0295(14) 0.0003(11)
C12B 0.0441(14) 0.0426(15) 0.084(2) -0.0008(13) 0.0296(14) -0.0081(12)
C13B 0.0471(15) 0.0324(13) 0.0603(16) -0.0027(11) 0.0223(12) -0.0052(11)
C14B 0.0567(17) 0.0397(15) 0.0750(19) 0.0037(13) 0.0339(14) 0.0007(13)
C15B 0.076(2) 0.0410(16) 0.082(2) 0.0031(14) 0.0286(17) 0.0052(14)
N1B 0.0416(12) 0.0347(11) 0.0615(13) 0.0009(9) 0.0205(10) -0.0015(9)
O1B 0.0830(17) 0.0354(12) 0.144(2) 0.0070(12) 0.0537(16) 0.0074(11)
O2B 0.0474(10) 0.0329(9) 0.0819(13) -0.0005(8) 0.0211(9) -0.0042(8)
O3B 0.0574(13) 0.0485(13) 0.180(3) 0.0174(14) 0.0580(16) 0.0037(10)
S1B 0.0390(4) 0.0340(4) 0.0752(5) -0.0003(3) 0.0243(3) -0.0032(2)
_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
C1A N1A 1.349(3) . ?
C1A C9A 1.394(3) . ?
C1A C10A 1.458(3) . ?
C2A N1A 1.341(3) . ?
C2A C7A 1.387(4) . ?
C2A C3A 1.505(4) . ?
C3A C4A 1.462(6) . ?
C3A C4A' 1.481(7) . ?
C3A H3A 0.9700 . ?
C3A H3B 0.9700 . ?
C4A C5A 1.522(6) . ?
C4A H4A 0.9700 . ?
C4A H4B 0.9700 . ?
C4A' C5A 1.431(8) . ?
C4A' H4A' 0.9700 . ?
C4A' H4B' 0.9700 . ?
C5A C6A 1.493(4) . ?
C5A H5A 0.9700 . ?
C5A H5B 0.9700 . ?
C6A O1A 1.205(3) . ?
C6A C7A 1.486(3) . ?
C7A C8A 1.390(4) . ?
C8A C9A 1.367(4) . ?
C8A H8A 0.9300 . ?
C9A H9A 0.9300 . ?
C10A C11A 1.364(3) . ?
C10A S1A 1.727(2) . ?
C11A C12A 1.402(4) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.343(4) . ?
C12A H12A 0.9300 . ?
C13A O2A 1.380(3) . ?
C13A S1A 1.725(2) . ?
C14A O3A 1.182(3) . ?
C14A O2A 1.351(3) . ?
C14A C15A 1.481(4) . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C1B N1B 1.344(3) . ?
C1B C9B 1.400(3) . ?
C1B C10B 1.459(3) . ?
C2B N1B 1.341(3) . ?
C2B C7B 1.391(3) . ?
C2B C3B 1.503(4) . ?
C3B C4B 1.427(7) . ?
C3B C4B' 1.533(9) . ?
C3B H3C 0.9700 . ?
C3B H3D 0.9700 . ?
C4B C5B 1.418(7) . ?
C4B H4C 0.9700 . ?
C4B H4D 0.9700 . ?
C4B' C5B 1.560(9) . ?
C4B' H4C' 0.9700 . ?
C4B' H4D' 0.9700 . ?
C5B C6B 1.500(4) . ?
C5B H5C 0.9700 . ?
C5B H5D 0.9700 . ?
C6B O1B 1.204(3) . ?
C6B C7B 1.486(4) . ?
C7B C8B 1.395(4) . ?
C8B C9B 1.365(4) . ?
C8B H8B 0.9300 . ?
C9B H9B 0.9300 . ?
C10B C11B 1.366(4) . ?
C10B S1B 1.727(3) . ?
C11B C12B 1.401(4) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.348(4) . ?
C12B H12B 0.9300 . ?
C13B O2B 1.382(3) . ?
C13B S1B 1.722(2) . ?
C14B O3B 1.183(3) . ?
C14B O2B 1.350(3) . ?
C14B C15B 1.485(4) . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1A C1A C9A 122.2(2) . . ?
N1A C1A C10A 116.5(2) . . ?
C9A C1A C10A 121.3(2) . . ?
N1A C2A C7A 123.0(2) . . ?
N1A C2A C3A 116.4(2) . . ?
C7A C2A C3A 120.6(2) . . ?
C4A C3A C2A 113.5(3) . . ?
C4A' C3A C2A 113.9(3) . . ?
C4A C3A H3A 108.9 . . ?
C4A' C3A H3A 133.9 . . ?
C2A C3A H3A 108.9 . . ?
C4A C3A H3B 108.9 . . ?
C4A' C3A H3B 74.3 . . ?
C2A C3A H3B 108.9 . . ?
H3A C3A H3B 107.7 . . ?
C3A C4A C5A 114.7(4) . . ?
C3A C4A H4A 108.6 . . ?
C5A C4A H4A 108.6 . . ?
C3A C4A H4B 108.6 . . ?
C5A C4A H4B 108.6 . . ?
H4A C4A H4B 107.6 . . ?
C5A C4A' C3A 119.3(6) . . ?
C5A C4A' H4A' 107.5 . . ?
C3A C4A' H4A' 107.5 . . ?
C5A C4A' H4B' 107.5 . . ?
C3A C4A' H4B' 107.5 . . ?
H4A' C4A' H4B' 107.0 . . ?
C4A' C5A C6A 115.0(4) . . ?
C6A C5A C4A 115.2(3) . . ?
C4A' C5A H5A 133.3 . . ?
C6A C5A H5A 108.5 . . ?
C4A C5A H5A 108.5 . . ?
C4A' C5A H5B 74.3 . . ?
C6A C5A H5B 108.5 . . ?
C4A C5A H5B 108.5 . . ?
H5A C5A H5B 107.5 . . ?
O1A C6A C7A 120.7(3) . . ?
O1A C6A C5A 121.9(3) . . ?
C7A C6A C5A 117.4(2) . . ?
C2A C7A C8A 118.1(2) . . ?
C2A C7A C6A 121.9(2) . . ?
C8A C7A C6A 120.0(2) . . ?
C9A C8A C7A 119.8(2) . . ?
C9A C8A H8A 120.1 . . ?
C7A C8A H8A 120.1 . . ?
C8A C9A C1A 118.9(2) . . ?
C8A C9A H9A 120.5 . . ?
C1A C9A H9A 120.5 . . ?
C11A C10A C1A 128.2(2) . . ?
C11A C10A S1A 111.36(19) . . ?
C1A C10A S1A 120.45(18) . . ?
C10A C11A C12A 113.5(2) . . ?
C10A C11A H11A 123.3 . . ?
C12A C11A H11A 123.3 . . ?
C13A C12A C11A 111.7(2) . . ?
C13A C12A H12A 124.1 . . ?
C11A C12A H12A 124.1 . . ?
C12A C13A O2A 120.7(2) . . ?
C12A C13A S1A 113.37(19) . . ?
O2A C13A S1A 125.85(19) . . ?
O3A C14A O2A 122.1(3) . . ?
O3A C14A C15A 126.6(3) . . ?
O2A C14A C15A 111.3(3) . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C2A N1A C1A 118.1(2) . . ?
C14A O2A C13A 121.8(2) . . ?
C13A S1A C10A 90.06(12) . . ?
N1B C1B C9B 122.1(2) . . ?
N1B C1B C10B 117.0(2) . . ?
C9B C1B C10B 120.8(2) . . ?
N1B C2B C7B 122.4(2) . . ?
N1B C2B C3B 117.0(2) . . ?
C7B C2B C3B 120.6(2) . . ?
C4B C3B C2B 116.0(3) . . ?
C2B C3B C4B' 109.8(4) . . ?
C4B C3B H3C 108.3 . . ?
C2B C3B H3C 108.3 . . ?
C4B' C3B H3C 93.3 . . ?
C4B C3B H3D 108.3 . . ?
C2B C3B H3D 108.3 . . ?
C4B' C3B H3D 127.6 . . ?
H3C C3B H3D 107.4 . . ?
C5B C4B C3B 123.5(5) . . ?
C5B C4B H4C 106.5 . . ?
C3B C4B H4C 106.5 . . ?
C5B C4B H4D 106.5 . . ?
C3B C4B H4D 106.5 . . ?
H4C C4B H4D 106.5 . . ?
C3B C4B' C5B 108.2(6) . . ?
C3B C4B' H4C' 110.1 . . ?
C5B C4B' H4C' 110.1 . . ?
C3B C4B' H4D' 110.1 . . ?
C5B C4B' H4D' 110.1 . . ?
H4C' C4B' H4D' 108.4 . . ?
C4B C5B C6B 118.3(3) . . ?
C6B C5B C4B' 111.9(4) . . ?
C4B C5B H5C 107.7 . . ?
C6B C5B H5C 107.7 . . ?
C4B' C5B H5C 126.7 . . ?
C4B C5B H5D 107.7 . . ?
C6B C5B H5D 107.7 . . ?
C4B' C5B H5D 93.3 . . ?
H5C C5B H5D 107.1 . . ?
O1B C6B C7B 121.3(3) . . ?
O1B C6B C5B 121.8(3) . . ?
C7B C6B C5B 116.8(2) . . ?
C2B C7B C8B 118.4(2) . . ?
C2B C7B C6B 122.1(2) . . ?
C8B C7B C6B 119.5(2) . . ?
C9B C8B C7B 119.6(2) . . ?
C9B C8B H8B 120.2 . . ?
C7B C8B H8B 120.2 . . ?
C8B C9B C1B 118.9(2) . . ?
C8B C9B H9B 120.6 . . ?
C1B C9B H9B 120.6 . . ?
C11B C10B C1B 128.2(2) . . ?
C11B C10B S1B 111.31(19) . . ?
C1B C10B S1B 120.45(19) . . ?
C10B C11B C12B 113.6(2) . . ?
C10B C11B H11B 123.2 . . ?
C12B C11B H11B 123.2 . . ?
C13B C12B C11B 111.6(2) . . ?
C13B C12B H12B 124.2 . . ?
C11B C12B H12B 124.2 . . ?
C12B C13B O2B 120.6(2) . . ?
C12B C13B S1B 113.41(19) . . ?
O2B C13B S1B 125.94(19) . . ?
O3B C14B O2B 122.4(3) . . ?
O3B C14B C15B 126.0(3) . . ?
O2B C14B C15B 111.6(3) . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C2B N1B C1B 118.6(2) . . ?
C14B O2B C13B 121.8(2) . . ?
C13B S1B C10B 90.14(12) . . ?
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
N1A C2A C3A C4A -154.8(4) . . . . ?
C7A C2A C3A C4A 25.5(5) . . . . ?
N1A C2A C3A C4A' 164.5(5) . . . . ?
C7A C2A C3A C4A' -15.3(6) . . . . ?
C4A' C3A C4A C5A 52.5(6) . . . . ?
C2A C3A C4A C5A -46.5(6) . . . . ?
C4A C3A C4A' C5A -61.4(8) . . . . ?
C2A C3A C4A' C5A 36.6(10) . . . . ?
C3A C4A' C5A C6A -41.1(10) . . . . ?
C3A C4A' C5A C4A 58.1(7) . . . . ?
C3A C4A C5A C4A' -55.7(6) . . . . ?
C3A C4A C5A C6A 43.0(7) . . . . ?
C4A' C5A C6A O1A -155.1(6) . . . . ?
C4A C5A C6A O1A 164.0(4) . . . . ?
C4A' C5A C6A C7A 23.9(6) . . . . ?
C4A C5A C6A C7A -17.1(5) . . . . ?
N1A C2A C7A C8A -0.4(4) . . . . ?
C3A C2A C7A C8A 179.4(3) . . . . ?
N1A C2A C7A C6A -179.5(2) . . . . ?
C3A C2A C7A C6A 0.3(4) . . . . ?
O1A C6A C7A C2A 174.7(3) . . . . ?
C5A C6A C7A C2A -4.2(4) . . . . ?
O1A C6A C7A C8A -4.4(4) . . . . ?
C5A C6A C7A C8A 176.7(3) . . . . ?
C2A C7A C8A C9A 0.4(4) . . . . ?
C6A C7A C8A C9A 179.5(3) . . . . ?
C7A C8A C9A C1A -0.2(4) . . . . ?
N1A C1A C9A C8A 0.0(4) . . . . ?
C10A C1A C9A C8A 179.6(2) . . . . ?
N1A C1A C10A C11A -178.0(3) . . . . ?
C9A C1A C10A C11A 2.4(4) . . . . ?
N1A C1A C10A S1A 2.3(3) . . . . ?
C9A C1A C10A S1A -177.3(2) . . . . ?
C1A C10A C11A C12A 179.6(3) . . . . ?
S1A C10A C11A C12A -0.7(3) . . . . ?
C10A C11A C12A C13A 0.4(4) . . . . ?
C11A C12A C13A O2A -177.5(2) . . . . ?
C11A C12A C13A S1A 0.1(3) . . . . ?
C7A C2A N1A C1A 0.2(4) . . . . ?
C3A C2A N1A C1A -179.6(2) . . . . ?
C9A C1A N1A C2A 0.0(4) . . . . ?
C10A C1A N1A C2A -179.6(2) . . . . ?
O3A C14A O2A C13A 1.3(5) . . . . ?
C15A C14A O2A C13A -179.5(2) . . . . ?
C12A C13A O2A C14A -172.5(3) . . . . ?
S1A C13A O2A C14A 10.2(4) . . . . ?
C12A C13A S1A C10A -0.4(2) . . . . ?
O2A C13A S1A C10A 177.1(2) . . . . ?
C11A C10A S1A C13A 0.6(2) . . . . ?
C1A C10A S1A C13A -179.7(2) . . . . ?
N1B C2B C3B C4B -169.0(4) . . . . ?
C7B C2B C3B C4B 11.1(5) . . . . ?
N1B C2B C3B C4B' -147.6(4) . . . . ?
C7B C2B C3B C4B' 32.5(5) . . . . ?
C2B C3B C4B C5B -19.6(9) . . . . ?
C4B' C3B C4B C5B -96.4(17) . . . . ?
C4B C3B C4B' C5B 52.5(13) . . . . ?
C2B C3B C4B' C5B -59.2(7) . . . . ?
C3B C4B C5B C6B 17.9(9) . . . . ?
C3B C4B C5B C4B' 94.2(16) . . . . ?
C3B C4B' C5B C4B -54.6(13) . . . . ?
C3B C4B' C5B C6B 58.2(7) . . . . ?
C4B C5B C6B O1B 174.7(5) . . . . ?
C4B' C5B C6B O1B 153.6(5) . . . . ?
C4B C5B C6B C7B -7.1(6) . . . . ?
C4B' C5B C6B C7B -28.3(6) . . . . ?
N1B C2B C7B C8B -2.3(4) . . . . ?
C3B C2B C7B C8B 177.6(3) . . . . ?
N1B C2B C7B C6B 178.4(2) . . . . ?
C3B C2B C7B C6B -1.7(4) . . . . ?
O1B C6B C7B C2B 177.8(3) . . . . ?
C5B C6B C7B C2B -0.4(4) . . . . ?
O1B C6B C7B C8B -1.6(4) . . . . ?
C5B C6B C7B C8B -179.7(3) . . . . ?
C2B C7B C8B C9B 1.6(4) . . . . ?
C6B C7B C8B C9B -179.1(3) . . . . ?
C7B C8B C9B C1B 0.3(4) . . . . ?
N1B C1B C9B C8B -1.8(4) . . . . ?
C10B C1B C9B C8B 177.5(3) . . . . ?
N1B C1B C10B C11B -179.3(3) . . . . ?
C9B C1B C10B C11B 1.4(4) . . . . ?
N1B C1B C10B S1B 1.9(3) . . . . ?
C9B C1B C10B S1B -177.4(2) . . . . ?
C1B C10B C11B C12B -179.9(3) . . . . ?
S1B C10B C11B C12B -1.0(3) . . . . ?
C10B C11B C12B C13B 0.9(4) . . . . ?
C11B C12B C13B O2B -177.6(2) . . . . ?
C11B C12B C13B S1B -0.4(3) . . . . ?
C7B C2B N1B C1B 0.9(4) . . . . ?
C3B C2B N1B C1B -179.0(2) . . . . ?
C9B C1B N1B C2B 1.1(4) . . . . ?
C10B C1B N1B C2B -178.1(2) . . . . ?
O3B C14B O2B C13B 2.8(5) . . . . ?
C15B C14B O2B C13B -178.3(2) . . . . ?
C12B C13B O2B C14B -171.5(3) . . . . ?
S1B C13B O2B C14B 11.7(4) . . . . ?
C12B C13B S1B C10B -0.1(2) . . . . ?
O2B C13B S1B C10B 176.9(2) . . . . ?
C11B C10B S1B C13B 0.6(2) . . . . ?
C1B C10B S1B C13B 179.6(2) . . . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.054


data_ap30
_database_code_depnum_ccdc_archive 'CCDC 902323'
#TrackingRef 'web_deposit_cif_file_2_B.Sridhar_1348129929.ap30f.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H23 N O3'
_chemical_formula_sum            'C25 H23 N O3'
_chemical_formula_weight         385.44
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_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                   16.2313(10)
_cell_length_b                   15.4503(10)
_cell_length_c                   8.0772(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.738(1)
_cell_angle_gamma                90.00
_cell_volume                     2011.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8199
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.69
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.083
_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      294(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_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19132
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3554
_reflns_number_gt                3043
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_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^)+(0.0568P)^2^+0.3683P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3554
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.08099(8) 0.65350(8) 0.54302(16) 0.0406(3) Uani 1 1 d . . .
C2 C 0.21896(8) 0.64190(8) 0.50412(17) 0.0435(3) Uani 1 1 d . . .
C3 C 0.28186(8) 0.63942(10) 0.38215(19) 0.0545(4) Uani 1 1 d . . .
H3A H 0.2950 0.6983 0.3530 0.065 Uiso 1 1 calc R . .
H3B H 0.2574 0.6108 0.2812 0.065 Uiso 1 1 calc R . .
C4 C 0.36224(9) 0.59296(11) 0.44653(19) 0.0576(4) Uani 1 1 d . . .
C5 C 0.39341(9) 0.63082(14) 0.6167(2) 0.0721(5) Uani 1 1 d . . .
H5A H 0.4407 0.5969 0.6642 0.087 Uiso 1 1 calc R . .
H5B H 0.4131 0.6891 0.6003 0.087 Uiso 1 1 calc R . .
C6 C 0.33187(9) 0.63448(10) 0.74140(19) 0.0565(4) Uani 1 1 d . . .
C7 C 0.24290(8) 0.64286(9) 0.67570(17) 0.0466(3) Uani 1 1 d . . .
C8 C 0.18168(9) 0.65168(9) 0.78141(17) 0.0513(3) Uani 1 1 d . . .
H8 H 0.1959 0.6529 0.8963 0.062 Uiso 1 1 calc R . .
C9 C 0.10007(9) 0.65862(9) 0.71526(17) 0.0484(3) Uani 1 1 d . . .
H9 H 0.0585 0.6666 0.7839 0.058 Uiso 1 1 calc R . .
C10 C -0.00625(8) 0.65544(8) 0.46265(15) 0.0396(3) Uani 1 1 d . . .
C11 C -0.06222(8) 0.71821(9) 0.50185(17) 0.0464(3) Uani 1 1 d . . .
H11 H -0.0451 0.7600 0.5813 0.056 Uiso 1 1 calc R . .
C12 C -0.14287(8) 0.71959(9) 0.42480(17) 0.0470(3) Uani 1 1 d . . .
H12 H -0.1787 0.7627 0.4531 0.056 Uiso 1 1 calc R . .
C13 C -0.17187(8) 0.65803(8) 0.30573(15) 0.0410(3) Uani 1 1 d . . .
C14 C -0.11617(8) 0.59350(8) 0.26973(15) 0.0406(3) Uani 1 1 d . . .
H14 H -0.1337 0.5502 0.1937 0.049 Uiso 1 1 calc R . .
C15 C -0.03583(7) 0.59354(8) 0.34565(15) 0.0379(3) Uani 1 1 d . . .
C16 C -0.25809(8) 0.66097(9) 0.21881(16) 0.0455(3) Uani 1 1 d . . .
C17 C -0.30415(10) 0.73660(12) 0.2111(2) 0.0697(5) Uani 1 1 d . . .
H17 H -0.2810 0.7864 0.2617 0.084 Uiso 1 1 calc R . .
C18 C -0.38396(11) 0.73941(15) 0.1296(3) 0.0838(6) Uani 1 1 d . . .
H18 H -0.4135 0.7911 0.1259 0.101 Uiso 1 1 calc R . .
C19 C -0.41998(10) 0.66734(14) 0.0545(2) 0.0742(5) Uani 1 1 d . . .
H19 H -0.4739 0.6695 0.0011 0.089 Uiso 1 1 calc R . .
C20 C -0.37536(10) 0.59177(13) 0.0589(2) 0.0701(5) Uani 1 1 d . . .
H20 H -0.3990 0.5423 0.0078 0.084 Uiso 1 1 calc R . .
C21 C -0.29513(9) 0.58891(11) 0.13926(19) 0.0581(4) Uani 1 1 d . . .
H21 H -0.2654 0.5374 0.1398 0.070 Uiso 1 1 calc R . .
C22 C 0.06095(8) 0.52991(9) 0.18474(16) 0.0448(3) Uani 1 1 d . . .
C23 C 0.12156(9) 0.45730(11) 0.1919(2) 0.0628(4) Uani 1 1 d . . .
H23A H 0.0945 0.4063 0.1446 0.094 Uiso 1 1 calc R . .
H23B H 0.1429 0.4463 0.3059 0.094 Uiso 1 1 calc R . .
H23C H 0.1664 0.4725 0.1300 0.094 Uiso 1 1 calc R . .
C24 C 0.34538(12) 0.49613(12) 0.4595(2) 0.0786(5) Uani 1 1 d . . .
H24A H 0.3011 0.4871 0.5266 0.118 Uiso 1 1 calc R . .
H24B H 0.3945 0.4675 0.5099 0.118 Uiso 1 1 calc R . .
H24C H 0.3299 0.4729 0.3500 0.118 Uiso 1 1 calc R . .
C25 C 0.42645(10) 0.60896(16) 0.3258(3) 0.0872(6) Uani 1 1 d . . .
H25A H 0.4039 0.5919 0.2155 0.131 Uiso 1 1 calc R . .
H25B H 0.4754 0.5757 0.3601 0.131 Uiso 1 1 calc R . .
H25C H 0.4403 0.6694 0.3261 0.131 Uiso 1 1 calc R . .
N1 N 0.13922(6) 0.64528(7) 0.43896(13) 0.0434(3) Uani 1 1 d . . .
O1 O 0.35415(7) 0.63371(9) 0.89059(14) 0.0782(4) Uani 1 1 d . . .
O2 O 0.01624(5) 0.52438(6) 0.31634(10) 0.0425(2) Uani 1 1 d . . .
O3 O 0.05020(6) 0.58427(7) 0.07980(12) 0.0598(3) 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 0.0423(7) 0.0361(7) 0.0432(7) -0.0003(5) 0.0041(5) -0.0004(5)
C2 0.0399(7) 0.0405(7) 0.0492(7) 0.0039(6) 0.0007(6) 0.0003(5)
C3 0.0423(7) 0.0636(9) 0.0574(8) 0.0110(7) 0.0054(6) 0.0026(6)
C4 0.0398(7) 0.0707(10) 0.0610(9) 0.0028(7) 0.0000(6) 0.0078(7)
C5 0.0419(8) 0.0928(13) 0.0784(11) -0.0074(10) -0.0067(8) 0.0001(8)
C6 0.0528(8) 0.0531(9) 0.0590(9) -0.0056(7) -0.0122(7) 0.0000(7)
C7 0.0461(7) 0.0419(7) 0.0497(8) -0.0024(6) -0.0036(6) -0.0019(6)
C8 0.0585(9) 0.0521(8) 0.0410(7) -0.0062(6) -0.0036(6) -0.0043(6)
C9 0.0495(8) 0.0516(8) 0.0444(7) -0.0071(6) 0.0064(6) -0.0026(6)
C10 0.0398(7) 0.0405(7) 0.0391(7) 0.0026(5) 0.0068(5) -0.0012(5)
C11 0.0465(7) 0.0450(8) 0.0483(7) -0.0080(6) 0.0078(6) -0.0005(6)
C12 0.0436(7) 0.0457(8) 0.0532(8) -0.0020(6) 0.0120(6) 0.0061(6)
C13 0.0386(7) 0.0440(7) 0.0413(7) 0.0062(5) 0.0090(5) -0.0003(5)
C14 0.0421(7) 0.0399(7) 0.0398(7) -0.0001(5) 0.0051(5) -0.0025(5)
C15 0.0402(7) 0.0358(6) 0.0387(6) 0.0037(5) 0.0088(5) 0.0024(5)
C16 0.0388(7) 0.0545(8) 0.0443(7) 0.0079(6) 0.0096(5) 0.0007(6)
C17 0.0504(9) 0.0686(11) 0.0880(12) -0.0064(9) -0.0013(8) 0.0119(8)
C18 0.0533(10) 0.0908(14) 0.1037(15) -0.0019(11) -0.0058(10) 0.0233(10)
C19 0.0420(8) 0.1085(15) 0.0702(11) 0.0092(10) -0.0021(7) 0.0057(9)
C20 0.0535(9) 0.0849(13) 0.0689(10) 0.0009(9) -0.0057(8) -0.0103(9)
C21 0.0473(8) 0.0608(9) 0.0647(9) 0.0038(7) 0.0002(7) -0.0009(7)
C22 0.0436(7) 0.0507(8) 0.0392(7) -0.0074(6) 0.0015(5) 0.0001(6)
C23 0.0552(9) 0.0696(10) 0.0641(9) -0.0120(8) 0.0093(7) 0.0149(7)
C24 0.0830(12) 0.0712(12) 0.0794(12) -0.0031(9) -0.0004(9) 0.0231(10)
C25 0.0440(9) 0.1314(18) 0.0869(13) 0.0074(12) 0.0109(8) 0.0131(10)
N1 0.0389(6) 0.0477(6) 0.0431(6) 0.0037(5) 0.0023(5) 0.0012(5)
O1 0.0661(7) 0.1011(10) 0.0609(7) -0.0080(6) -0.0192(6) 0.0068(7)
O2 0.0436(5) 0.0386(5) 0.0456(5) 0.0004(4) 0.0072(4) 0.0047(4)
O3 0.0661(7) 0.0703(7) 0.0435(5) 0.0059(5) 0.0087(5) 0.0060(5)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3426(16) . ?
C1 C9 1.3916(19) . ?
C1 C10 1.4871(17) . ?
C2 N1 1.3398(16) . ?
C2 C7 1.3948(19) . ?
C2 C3 1.5001(19) . ?
C3 C4 1.5261(19) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.525(2) . ?
C4 C24 1.527(3) . ?
C4 C25 1.529(2) . ?
C5 C6 1.500(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O1 1.2169(18) . ?
C6 C7 1.4845(19) . ?
C7 C8 1.391(2) . ?
C8 C9 1.3732(19) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.3900(18) . ?
C10 C11 1.3906(18) . ?
C11 C12 1.3821(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.3946(19) . ?
C12 H12 0.9300 . ?
C13 C14 1.3991(18) . ?
C13 C16 1.4909(18) . ?
C14 C15 1.3744(17) . ?
C14 H14 0.9300 . ?
C15 O2 1.3996(14) . ?
C16 C17 1.385(2) . ?
C16 C21 1.387(2) . ?
C17 C18 1.383(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.366(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 O3 1.1914(16) . ?
C22 O2 1.3582(15) . ?
C22 C23 1.489(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C9 122.74(12) . . ?
N1 C1 C10 115.65(11) . . ?
C9 C1 C10 121.61(12) . . ?
N1 C2 C7 122.25(12) . . ?
N1 C2 C3 116.33(12) . . ?
C7 C2 C3 121.40(12) . . ?
C2 C3 C4 114.13(12) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C3 107.86(13) . . ?
C5 C4 C24 110.95(15) . . ?
C3 C4 C24 109.35(13) . . ?
C5 C4 C25 109.52(14) . . ?
C3 C4 C25 109.04(13) . . ?
C24 C4 C25 110.08(16) . . ?
C6 C5 C4 116.30(13) . . ?
C6 C5 H5A 108.2 . . ?
C4 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
C4 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
O1 C6 C7 121.22(15) . . ?
O1 C6 C5 121.36(14) . . ?
C7 C6 C5 117.36(13) . . ?
C8 C7 C2 118.37(12) . . ?
C8 C7 C6 121.62(13) . . ?
C2 C7 C6 120.01(13) . . ?
C9 C8 C7 119.66(13) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C1 118.42(13) . . ?
C8 C9 H9 120.8 . . ?
C1 C9 H9 120.8 . . ?
C15 C10 C11 116.86(11) . . ?
C15 C10 C1 121.21(11) . . ?
C11 C10 C1 121.92(11) . . ?
C12 C11 C10 121.19(12) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 121.68(12) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C14 117.09(11) . . ?
C12 C13 C16 121.75(12) . . ?
C14 C13 C16 121.16(12) . . ?
C15 C14 C13 120.62(12) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 122.52(11) . . ?
C14 C15 O2 118.98(11) . . ?
C10 C15 O2 118.23(11) . . ?
C17 C16 C21 117.01(13) . . ?
C17 C16 C13 121.25(13) . . ?
C21 C16 C13 121.72(12) . . ?
C18 C17 C16 121.23(17) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 120.92(18) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.01(15) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C19 C20 C21 120.22(17) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 121.60(15) . . ?
C20 C21 H21 119.2 . . ?
C16 C21 H21 119.2 . . ?
O3 C22 O2 123.64(12) . . ?
O3 C22 C23 126.87(13) . . ?
O2 C22 C23 109.47(12) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C4 C24 H24A 109.5 . . ?
C4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C4 C25 H25A 109.5 . . ?
C4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C2 N1 C1 118.45(11) . . ?
C22 O2 C15 118.24(10) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -151.49(13) . . . . ?
C7 C2 C3 C4 30.1(2) . . . . ?
C2 C3 C4 C5 -50.90(18) . . . . ?
C2 C3 C4 C24 69.85(18) . . . . ?
C2 C3 C4 C25 -169.75(14) . . . . ?
C3 C4 C5 C6 51.2(2) . . . . ?
C24 C4 C5 C6 -68.55(19) . . . . ?
C25 C4 C5 C6 169.73(15) . . . . ?
C4 C5 C6 O1 153.84(16) . . . . ?
C4 C5 C6 C7 -28.7(2) . . . . ?
N1 C2 C7 C8 -3.0(2) . . . . ?
C3 C2 C7 C8 175.27(13) . . . . ?
N1 C2 C7 C6 176.89(12) . . . . ?
C3 C2 C7 C6 -4.79(19) . . . . ?
O1 C6 C7 C8 1.2(2) . . . . ?
C5 C6 C7 C8 -176.31(14) . . . . ?
O1 C6 C7 C2 -178.78(15) . . . . ?
C5 C6 C7 C2 3.8(2) . . . . ?
C2 C7 C8 C9 0.4(2) . . . . ?
C6 C7 C8 C9 -179.54(13) . . . . ?
C7 C8 C9 C1 2.2(2) . . . . ?
N1 C1 C9 C8 -2.5(2) . . . . ?
C10 C1 C9 C8 176.49(12) . . . . ?
N1 C1 C10 C15 49.31(16) . . . . ?
C9 C1 C10 C15 -129.77(14) . . . . ?
N1 C1 C10 C11 -131.44(13) . . . . ?
C9 C1 C10 C11 49.47(18) . . . . ?
C15 C10 C11 C12 -1.36(19) . . . . ?
C1 C10 C11 C12 179.37(12) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C11 C12 C13 C14 1.25(19) . . . . ?
C11 C12 C13 C16 -178.14(12) . . . . ?
C12 C13 C14 C15 -2.10(18) . . . . ?
C16 C13 C14 C15 177.30(11) . . . . ?
C13 C14 C15 C10 1.26(18) . . . . ?
C13 C14 C15 O2 175.14(11) . . . . ?
C11 C10 C15 C14 0.50(18) . . . . ?
C1 C10 C15 C14 179.78(11) . . . . ?
C11 C10 C15 O2 -173.42(11) . . . . ?
C1 C10 C15 O2 5.86(17) . . . . ?
C12 C13 C16 C17 20.5(2) . . . . ?
C14 C13 C16 C17 -158.84(14) . . . . ?
C12 C13 C16 C21 -160.84(13) . . . . ?
C14 C13 C16 C21 19.79(19) . . . . ?
C21 C16 C17 C18 0.9(2) . . . . ?
C13 C16 C17 C18 179.62(16) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C20 -0.8(3) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C19 C20 C21 C16 0.9(3) . . . . ?
C17 C16 C21 C20 -1.5(2) . . . . ?
C13 C16 C21 C20 179.84(14) . . . . ?
C7 C2 N1 C1 2.84(18) . . . . ?
C3 C2 N1 C1 -175.56(12) . . . . ?
C9 C1 N1 C2 -0.01(18) . . . . ?
C10 C1 N1 C2 -179.08(11) . . . . ?
O3 C22 O2 C15 -10.67(18) . . . . ?
C23 C22 O2 C15 170.98(11) . . . . ?
C14 C15 O2 C22 89.09(13) . . . . ?
C10 C15 O2 C22 -96.77(13) . . . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.032