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

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

data_VC1548
_database_code_depnum_ccdc_archive 'CCDC 1062833'
_audit_update_record             
;
2015-05-02 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;

ethyl 6-(9-methyl-9H-carbazol-3-yl)-1-oxo-3-phenyl-1H-indene-2-carboxylate
;
_chemical_formula_moiety         'C31 H23 N O3'
_chemical_formula_sum            'C31 H23 N O3'
_chemical_formula_weight         457.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.1488(12)
_cell_length_b                   12.408(3)
_cell_length_c                   20.320(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.682(15)
_cell_angle_gamma                90
_cell_volume                     2302.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_oxdiff_measurement_reflns_used 2967

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_min  0.81472
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.0827
_diffrn_reflns_number            17755
_diffrn_reflns_av_unetI/netI     0.1754
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.387
_diffrn_reflns_theta_max         29.105
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5415
_reflns_number_gt                1865
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5415
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1681
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   0.727
_refine_ls_restrained_S_all      0.727
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2500(2) 0.0498(2) 0.09169(12) 0.0516(7) Uani 1 1 d . . . . .
O1 O 0.14722(16) 0.10286(16) 0.07037(9) 0.0753(6) Uani 1 1 d . . . . .
C2 C 0.2485(2) -0.0453(2) 0.13688(12) 0.0433(6) Uani 1 1 d . . . . .
C3 C 0.3889(2) -0.07927(19) 0.15059(10) 0.0385(6) Uani 1 1 d . . . . .
C4 C 0.4900(2) -0.00928(19) 0.11638(11) 0.0395(6) Uani 1 1 d . . . . .
C5 C 0.6406(2) -0.0083(2) 0.11351(11) 0.0442(6) Uani 1 1 d . . . . .
H5 H 0.6977 -0.0616 0.1346 0.053 Uiso 1 1 calc R U . . .
C6 C 0.7056(2) 0.0732(2) 0.07879(11) 0.0450(6) Uani 1 1 d . . . . .
H6 H 0.8071 0.0738 0.0775 0.054 Uiso 1 1 calc R U . . .
C7 C 0.6249(2) 0.1542(2) 0.04578(11) 0.0423(6) Uani 1 1 d . . . . .
C8 C 0.4708(2) 0.1479(2) 0.04602(11) 0.0478(7) Uani 1 1 d . . . . .
H8 H 0.4123 0.1972 0.0221 0.057 Uiso 1 1 calc R U . . .
C9 C 0.4081(2) 0.0691(2) 0.08154(11) 0.0426(6) Uani 1 1 d . . . . .
C10 C 0.1108(3) -0.0863(2) 0.16028(14) 0.0505(7) Uani 1 1 d . . . . .
O2 O -0.00634(16) -0.07700(15) 0.13034(9) 0.0696(6) Uani 1 1 d . . . . .
O3 O 0.12679(16) -0.12926(15) 0.22033(9) 0.0695(6) Uani 1 1 d . . . . .
C11 C -0.0018(3) -0.1799(3) 0.2451(2) 0.0996(12) Uani 1 1 d . . . . .
H11A H -0.0697 -0.1246 0.2576 0.120 Uiso 0.51(2) 1 calc R U P A 1
H11B H -0.0505 -0.2230 0.2104 0.120 Uiso 0.51(2) 1 calc R U P A 1
H11C H -0.0257 -0.1436 0.2853 0.120 Uiso 0.49(2) 1 calc R U P A 2
H11D H -0.0839 -0.1703 0.2130 0.120 Uiso 0.49(2) 1 calc R U P A 2
C12A C 0.0343(13) -0.243(2) 0.2976(11) 0.186(11) Uani 0.51(2) 1 d . . P A 1
H12A H 0.0837 -0.3062 0.2833 0.280 Uiso 0.51(2) 1 calc R U P A 1
H12B H -0.0529 -0.2636 0.3182 0.280 Uiso 0.51(2) 1 calc R U P A 1
H12C H 0.0978 -0.2039 0.3285 0.280 Uiso 0.51(2) 1 calc R U P A 1
C12B C 0.0161(13) -0.2891(8) 0.2581(8) 0.086(4) Uani 0.49(2) 1 d . . P A 2
H12D H 0.0004 -0.3291 0.2178 0.128 Uiso 0.49(2) 1 calc R U P A 2
H12E H -0.0535 -0.3117 0.2887 0.128 Uiso 0.49(2) 1 calc R U P A 2
H12F H 0.1136 -0.3020 0.2767 0.128 Uiso 0.49(2) 1 calc R U P A 2
C13 C 0.6951(2) 0.2435(2) 0.01186(11) 0.0403(6) Uani 1 1 d . . . . .
C14 C 0.6173(2) 0.3413(2) -0.00016(12) 0.0543(7) Uani 1 1 d . . . . .
H14 H 0.5223 0.3463 0.0133 0.065 Uiso 1 1 calc R U . . .
C15 C 0.6755(2) 0.4292(2) -0.03089(12) 0.0550(7) Uani 1 1 d . . . . .
H15 H 0.6210 0.4918 -0.0384 0.066 Uiso 1 1 calc R U . . .
C16 C 0.8169(2) 0.4214(2) -0.05012(11) 0.0460(6) Uani 1 1 d . . . . .
N17 N 0.9005(2) 0.49552(17) -0.08061(10) 0.0515(6) Uani 1 1 d . . . . .
C18 C 1.0353(2) 0.4511(2) -0.09059(11) 0.0467(7) Uani 1 1 d . . . . .
C19 C 1.1546(3) 0.4952(2) -0.11858(12) 0.0611(8) Uani 1 1 d . . . . .
H19 H 1.1520 0.5654 -0.1346 0.073 Uiso 1 1 calc R U . . .
C20 C 1.2774(3) 0.4328(3) -0.12223(13) 0.0680(8) Uani 1 1 d . . . . .
H20 H 1.3590 0.4613 -0.1411 0.082 Uiso 1 1 calc R U . . .
C21 C 1.2826(3) 0.3277(3) -0.09839(13) 0.0610(8) Uani 1 1 d . . . . .
H21 H 1.3668 0.2868 -0.1023 0.073 Uiso 1 1 calc R U . . .
C22 C 1.1658(2) 0.2836(2) -0.06932(12) 0.0529(7) Uani 1 1 d . . . . .
H22 H 1.1704 0.2138 -0.0527 0.063 Uiso 1 1 calc R U . . .
C23 C 1.0394(2) 0.3460(2) -0.06527(11) 0.0451(7) Uani 1 1 d . . . . .
C24 C 0.8990(2) 0.3259(2) -0.03875(11) 0.0419(6) Uani 1 1 d . . . . .
C25 C 0.8374(2) 0.2383(2) -0.00784(11) 0.0447(6) Uani 1 1 d . . . . .
H25 H 0.8920 0.1758 -0.0003 0.054 Uiso 1 1 calc R U . . .
C26 C 0.8510(3) 0.6018(2) -0.10280(13) 0.0657(8) Uani 1 1 d . . . . .
H26A H 0.7656 0.6217 -0.0805 0.099 Uiso 1 1 calc R U . . .
H26B H 0.8273 0.6002 -0.1495 0.099 Uiso 1 1 calc R U . . .
H26C H 0.9273 0.6535 -0.0930 0.099 Uiso 1 1 calc R U . . .
C1' C 0.4384(2) -0.1721(2) 0.19082(11) 0.0419(6) Uani 1 1 d . . . . .
C2' C 0.3703(2) -0.2717(2) 0.18352(12) 0.0527(7) Uani 1 1 d . . . . .
H2' H 0.2925 -0.2803 0.1522 0.063 Uiso 1 1 calc R U . . .
C3' C 0.4163(3) -0.3579(2) 0.22211(14) 0.0636(8) Uani 1 1 d . . . . .
H3' H 0.3697 -0.4242 0.2166 0.076 Uiso 1 1 calc R U . . .
C4' C 0.5303(3) -0.3464(2) 0.26858(14) 0.0666(8) Uani 1 1 d . . . . .
H4' H 0.5600 -0.4045 0.2951 0.080 Uiso 1 1 calc R U . . .
C5' C 0.6003(3) -0.2493(3) 0.27590(13) 0.0602(8) Uani 1 1 d . . . . .
H5' H 0.6785 -0.2421 0.3071 0.072 Uiso 1 1 calc R U . . .
C6' C 0.5563(2) -0.1620(2) 0.23747(12) 0.0502(7) Uani 1 1 d . . . . .
H6' H 0.6052 -0.0965 0.2427 0.060 Uiso 1 1 calc R U . . .


_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 1.205(3) . ?
C1 C9 1.494(3) . ?
C1 C2 1.495(3) . ?
C2 C3 1.363(3) . ?
C2 C10 1.466(3) . ?
C3 C1' 1.467(3) . ?
C3 C4 1.475(3) . ?
C4 C5 1.383(3) . ?
C4 C9 1.393(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.413(3) . ?
C7 C13 1.474(3) . ?
C8 C9 1.363(3) . ?
C8 H8 0.9300 . ?
C10 O2 1.203(3) . ?
C10 O3 1.331(3) . ?
O3 C11 1.452(3) . ?
C11 C12A 1.346(12) . ?
C11 C12B 1.388(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13 C25 1.388(3) . ?
C13 C14 1.420(3) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C16 N17 1.370(3) . ?
C16 C24 1.414(3) . ?
N17 C18 1.377(3) . ?
N17 C26 1.456(3) . ?
C18 C19 1.377(3) . ?
C18 C23 1.402(3) . ?
C19 C20 1.370(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.399(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.446(3) . ?
C24 C25 1.393(3) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C1' C2' 1.388(3) . ?
C1' C6' 1.395(3) . ?
C2' C3' 1.376(3) . ?
C2' H2' 0.9300 . ?
C3' C4' 1.368(3) . ?
C3' H3' 0.9300 . ?
C4' C5' 1.368(4) . ?
C4' H4' 0.9300 . ?
C5' C6' 1.380(3) . ?
C5' H5' 0.9300 . ?
C6' H6' 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C9 127.0(2) . . ?
O1 C1 C2 127.9(2) . . ?
C9 C1 C2 105.0(2) . . ?
C3 C2 C10 130.1(2) . . ?
C3 C2 C1 108.92(19) . . ?
C10 C2 C1 120.9(2) . . ?
C2 C3 C1' 127.6(2) . . ?
C2 C3 C4 109.4(2) . . ?
C1' C3 C4 122.97(18) . . ?
C5 C4 C9 118.5(2) . . ?
C5 C4 C3 133.0(2) . . ?
C9 C4 C3 108.51(17) . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 122.59(19) . . ?
C5 C6 H6 118.7 . . ?
C7 C6 H6 118.7 . . ?
C6 C7 C8 117.2(2) . . ?
C6 C7 C13 122.25(19) . . ?
C8 C7 C13 120.5(2) . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C4 122.63(19) . . ?
C8 C9 C1 129.2(2) . . ?
C4 C9 C1 108.2(2) . . ?
O2 C10 O3 122.9(2) . . ?
O2 C10 C2 124.0(3) . . ?
O3 C10 C2 113.0(2) . . ?
C10 O3 C11 116.6(2) . . ?
C12A C11 O3 111.3(6) . . ?
C12B C11 O3 113.6(5) . . ?
C12A C11 H11A 109.4 . . ?
O3 C11 H11A 109.4 . . ?
C12A C11 H11B 109.4 . . ?
O3 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C12B C11 H11C 108.9 . . ?
O3 C11 H11C 108.9 . . ?
C12B C11 H11D 108.9 . . ?
O3 C11 H11D 108.9 . . ?
H11C C11 H11D 107.7 . . ?
C11 C12A H12A 109.5 . . ?
C11 C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11 C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11 C12B H12D 109.5 . . ?
C11 C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11 C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C25 C13 C14 117.3(2) . . ?
C25 C13 C7 123.0(2) . . ?
C14 C13 C7 119.6(2) . . ?
C15 C14 C13 123.3(2) . . ?
C15 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
C16 C15 C14 118.0(2) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
N17 C16 C15 130.0(2) . . ?
N17 C16 C24 109.26(19) . . ?
C15 C16 C24 120.7(2) . . ?
C16 N17 C18 109.2(2) . . ?
C16 N17 C26 125.15(19) . . ?
C18 N17 C26 125.5(2) . . ?
C19 C18 N17 130.0(3) . . ?
C19 C18 C23 121.2(2) . . ?
N17 C18 C23 108.7(2) . . ?
C20 C19 C18 118.2(3) . . ?
C20 C19 H19 120.9 . . ?
C18 C19 H19 120.9 . . ?
C19 C20 C21 121.4(2) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 121.0(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 118.4(3) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C22 C23 C18 119.7(2) . . ?
C22 C23 C24 133.2(3) . . ?
C18 C23 C24 107.1(2) . . ?
C25 C24 C16 120.1(2) . . ?
C25 C24 C23 134.2(2) . . ?
C16 C24 C23 105.7(2) . . ?
C13 C25 C24 120.6(2) . . ?
C13 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
N17 C26 H26A 109.5 . . ?
N17 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N17 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C2' C1' C6' 118.3(2) . . ?
C2' C1' C3 121.3(2) . . ?
C6' C1' C3 120.4(2) . . ?
C3' C2' C1' 120.8(2) . . ?
C3' C2' H2' 119.6 . . ?
C1' C2' H2' 119.6 . . ?
C4' C3' C2' 120.3(3) . . ?
C4' C3' H3' 119.9 . . ?
C2' C3' H3' 119.9 . . ?
C5' C4' C3' 119.8(3) . . ?
C5' C4' H4' 120.1 . . ?
C3' C4' H4' 120.1 . . ?
C4' C5' C6' 120.8(3) . . ?
C4' C5' H5' 119.6 . . ?
C6' C5' H5' 119.6 . . ?
C5' C6' C1' 119.9(3) . . ?
C5' C6' H6' 120.0 . . ?
C1' C6' H6' 120.0 . . ?

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 C3 -177.9(3) . . . . ?
C9 C1 C2 C3 -1.1(3) . . . . ?
O1 C1 C2 C10 0.9(4) . . . . ?
C9 C1 C2 C10 177.7(2) . . . . ?
C10 C2 C3 C1' 3.7(4) . . . . ?
C1 C2 C3 C1' -177.6(2) . . . . ?
C10 C2 C3 C4 -178.2(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -179.9(2) . . . . ?
C1' C3 C4 C5 -1.6(4) . . . . ?
C2 C3 C4 C9 0.3(3) . . . . ?
C1' C3 C4 C9 178.6(2) . . . . ?
C9 C4 C5 C6 3.0(3) . . . . ?
C3 C4 C5 C6 -176.7(2) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C5 C6 C7 C8 -3.0(3) . . . . ?
C5 C6 C7 C13 176.8(2) . . . . ?
C6 C7 C8 C9 4.5(3) . . . . ?
C13 C7 C8 C9 -175.4(2) . . . . ?
C7 C8 C9 C4 -2.4(4) . . . . ?
C7 C8 C9 C1 176.9(2) . . . . ?
C5 C4 C9 C8 -1.5(4) . . . . ?
C3 C4 C9 C8 178.3(2) . . . . ?
C5 C4 C9 C1 179.1(2) . . . . ?
C3 C4 C9 C1 -1.0(3) . . . . ?
O1 C1 C9 C8 -1.1(4) . . . . ?
C2 C1 C9 C8 -178.0(2) . . . . ?
O1 C1 C9 C4 178.2(2) . . . . ?
C2 C1 C9 C4 1.3(3) . . . . ?
C3 C2 C10 O2 -153.9(3) . . . . ?
C1 C2 C10 O2 27.5(4) . . . . ?
C3 C2 C10 O3 30.0(4) . . . . ?
C1 C2 C10 O3 -148.5(2) . . . . ?
O2 C10 O3 C11 8.8(4) . . . . ?
C2 C10 O3 C11 -175.0(2) . . . . ?
C10 O3 C11 C12A 164.6(16) . . . . ?
C10 O3 C11 C12B 118.5(9) . . . . ?
C6 C7 C13 C25 20.6(4) . . . . ?
C8 C7 C13 C25 -159.5(2) . . . . ?
C6 C7 C13 C14 -157.6(2) . . . . ?
C8 C7 C13 C14 22.3(3) . . . . ?
C25 C13 C14 C15 0.9(4) . . . . ?
C7 C13 C14 C15 179.2(2) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C14 C15 C16 N17 -179.4(2) . . . . ?
C14 C15 C16 C24 0.2(4) . . . . ?
C15 C16 N17 C18 -179.5(2) . . . . ?
C24 C16 N17 C18 0.8(3) . . . . ?
C15 C16 N17 C26 -3.3(4) . . . . ?
C24 C16 N17 C26 177.1(2) . . . . ?
C16 N17 C18 C19 -179.2(2) . . . . ?
C26 N17 C18 C19 4.5(4) . . . . ?
C16 N17 C18 C23 -0.6(3) . . . . ?
C26 N17 C18 C23 -176.9(2) . . . . ?
N17 C18 C19 C20 179.7(2) . . . . ?
C23 C18 C19 C20 1.2(4) . . . . ?
C18 C19 C20 C21 -0.1(4) . . . . ?
C19 C20 C21 C22 -1.2(4) . . . . ?
C20 C21 C22 C23 1.3(4) . . . . ?
C21 C22 C23 C18 -0.2(4) . . . . ?
C21 C22 C23 C24 179.8(2) . . . . ?
C19 C18 C23 C22 -1.1(4) . . . . ?
N17 C18 C23 C22 -179.8(2) . . . . ?
C19 C18 C23 C24 178.9(2) . . . . ?
N17 C18 C23 C24 0.2(3) . . . . ?
N17 C16 C24 C25 179.7(2) . . . . ?
C15 C16 C24 C25 0.0(4) . . . . ?
N17 C16 C24 C23 -0.7(3) . . . . ?
C15 C16 C24 C23 179.6(2) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
C18 C23 C24 C25 179.8(3) . . . . ?
C22 C23 C24 C16 -179.7(2) . . . . ?
C18 C23 C24 C16 0.3(3) . . . . ?
C14 C13 C25 C24 -0.7(3) . . . . ?
C7 C13 C25 C24 -178.9(2) . . . . ?
C16 C24 C25 C13 0.2(4) . . . . ?
C23 C24 C25 C13 -179.2(2) . . . . ?
C2 C3 C1' C2' 45.6(3) . . . . ?
C4 C3 C1' C2' -132.3(2) . . . . ?
C2 C3 C1' C6' -134.6(2) . . . . ?
C4 C3 C1' C6' 47.5(3) . . . . ?
C6' C1' C2' C3' 1.1(3) . . . . ?
C3 C1' C2' C3' -179.1(2) . . . . ?
C1' C2' C3' C4' 0.2(4) . . . . ?
C2' C3' C4' C5' -1.1(4) . . . . ?
C3' C4' C5' C6' 0.8(4) . . . . ?
C4' C5' C6' C1' 0.5(4) . . . . ?
C2' C1' C6' C5' -1.4(3) . . . . ?
C3 C1' C6' C5' 178.8(2) . . . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_VC1643
_database_code_depnum_ccdc_archive 'CCDC 1062836'
_audit_update_record             
;
2015-05-02 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
'ethyl 6-(4-(diphenylamino)phenyl)-1-oxo-3-phenyl-1H-indene-2-carboxylate'

_chemical_formula_moiety         'C36 H27 N O3'
_chemical_formula_sum            'C36 H27 N O3'
_chemical_formula_weight         521.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      Monoclinic
_space_group_name_H-M_alt        'P 21/a'
_space_group_name_Hall           '-P 2yab'


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

_cell_length_a                   18.295(3)
_cell_length_b                   8.6639(8)
_cell_length_c                   19.269(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.79(2)
_cell_angle_gamma                90
_cell_volume                     2750.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    734
_cell_measurement_theta_min      2.1204
_cell_measurement_theta_max      28.9067

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_min  0.03895
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.0827
_diffrn_reflns_number            12655
_diffrn_reflns_av_unetI/netI     0.2985
_diffrn_reflns_av_R_equivalents  0.1133
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.229
_diffrn_reflns_theta_max         28.971
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6225
_reflns_number_gt                1707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00050(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6225
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3134
_refine_ls_R_factor_gt           0.0804
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_restrained_S_all      0.904
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4406(3) 0.0891(5) 0.3568(3) 0.0417(13) Uani 1 1 d . . . . .
O1 O 0.5014(2) 0.0292(3) 0.40565(19) 0.0611(11) Uani 1 1 d . . . . .
C2 C 0.4217(3) 0.1223(5) 0.2741(3) 0.0401(13) Uani 1 1 d . . . . .
C3 C 0.3493(3) 0.1934(5) 0.2396(3) 0.0358(12) Uani 1 1 d . . . . .
C4 C 0.3140(3) 0.2079(4) 0.2962(3) 0.0356(12) Uani 1 1 d . . . . .
C5 C 0.2433(3) 0.2745(5) 0.2901(3) 0.0426(13) Uani 1 1 d . . . . .
H5 H 0.2074 0.3207 0.2443 0.051 Uiso 1 1 calc R U . . .
C6 C 0.2266(3) 0.2711(5) 0.3546(3) 0.0451(14) Uani 1 1 d . . . . .
H6 H 0.1781 0.3132 0.3504 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2803(3) 0.2068(4) 0.4249(3) 0.0365(13) Uani 1 1 d . . . . .
C8 C 0.3536(3) 0.1443(4) 0.4300(3) 0.0409(13) Uani 1 1 d . . . . .
H8 H 0.3919 0.1039 0.4763 0.049 Uiso 1 1 calc R U . . .
C9 C 0.3676(3) 0.1442(5) 0.3657(3) 0.0367(13) Uani 1 1 d . . . . .
C10 C 0.4799(3) 0.0819(6) 0.2428(3) 0.0488(15) Uani 1 1 d . . . . .
O2 O 0.5517(2) 0.0890(4) 0.2781(2) 0.0826(13) Uani 1 1 d . . . . .
O3 O 0.4432(2) 0.0273(4) 0.1713(2) 0.0581(10) Uani 1 1 d . . . . .
C11 C 0.4960(3) -0.0109(6) 0.1349(3) 0.0794(19) Uani 1 1 d . . . . .
H11A H 0.4694 -0.0871 0.0949 0.095 Uiso 1 1 calc R U . . .
H11B H 0.5458 -0.0563 0.1730 0.095 Uiso 1 1 calc R U . . .
C12 C 0.5160(4) 0.1249(6) 0.1011(3) 0.115(3) Uani 1 1 d . . . . .
H12A H 0.5435 0.0927 0.0710 0.173 Uiso 1 1 calc R U . . .
H12B H 0.5506 0.1925 0.1415 0.173 Uiso 1 1 calc R U . . .
H12C H 0.4670 0.1783 0.0687 0.173 Uiso 1 1 calc R U . . .
C13 C 0.3112(3) 0.2598(5) 0.1621(3) 0.0413(13) Uani 1 1 d . . . . .
C14 C 0.3545(3) 0.3590(5) 0.1374(3) 0.0617(17) Uani 1 1 d . . . . .
H14 H 0.4082 0.3825 0.1700 0.074 Uiso 1 1 calc R U . . .
C15 C 0.3180(4) 0.4230(7) 0.0646(4) 0.087(2) Uani 1 1 d . . . . .
H15 H 0.3473 0.4904 0.0486 0.104 Uiso 1 1 calc R U . . .
C16 C 0.2391(4) 0.3882(7) 0.0155(4) 0.086(2) Uani 1 1 d . . . . .
H16 H 0.2150 0.4307 -0.0337 0.103 Uiso 1 1 calc R U . . .
C17 C 0.1962(3) 0.2908(6) 0.0395(3) 0.0737(19) Uani 1 1 d . . . . .
H17 H 0.1426 0.2670 0.0065 0.088 Uiso 1 1 calc R U . . .
C18 C 0.2316(3) 0.2270(5) 0.1126(3) 0.0540(15) Uani 1 1 d . . . . .
H18 H 0.2016 0.1614 0.1285 0.065 Uiso 1 1 calc R U . . .
C19 C 0.2595(3) 0.2081(4) 0.4913(3) 0.0323(12) Uani 1 1 d . . . . .
C20 C 0.3157(3) 0.1581(5) 0.5645(3) 0.0428(13) Uani 1 1 d . . . . .
H20 H 0.3665 0.1241 0.5710 0.051 Uiso 1 1 calc R U . . .
C21 C 0.2976(3) 0.1581(4) 0.6267(3) 0.0429(14) Uani 1 1 d . . . . .
H21 H 0.3361 0.1237 0.6744 0.051 Uiso 1 1 calc R U . . .
C22 C 0.2222(3) 0.2091(5) 0.6190(3) 0.0384(13) Uani 1 1 d . . . . .
C23 C 0.1660(3) 0.2599(5) 0.5477(3) 0.0446(14) Uani 1 1 d . . . . .
H23 H 0.1157 0.2958 0.5417 0.054 Uiso 1 1 calc R U . . .
C24 C 0.1844(3) 0.2575(5) 0.4854(3) 0.0432(13) Uani 1 1 d . . . . .
H24 H 0.1452 0.2900 0.4376 0.052 Uiso 1 1 calc R U . . .
C25 C 0.2667(3) 0.2557(5) 0.7565(3) 0.0434(14) Uani 1 1 d . . . . .
C26 C 0.3181(3) 0.3750(5) 0.7602(3) 0.0516(15) Uani 1 1 d . . . . .
H26 H 0.3106 0.4272 0.7155 0.062 Uiso 1 1 calc R U . . .
C27 C 0.3810(3) 0.4179(6) 0.8301(4) 0.0666(18) Uani 1 1 d . . . . .
H27 H 0.4165 0.4960 0.8316 0.080 Uiso 1 1 calc R U . . .
C28 C 0.3911(4) 0.3460(6) 0.8970(3) 0.076(2) Uani 1 1 d . . . . .
H28 H 0.4326 0.3759 0.9440 0.091 Uiso 1 1 calc R U . . .
C29 C 0.3385(4) 0.2278(6) 0.8934(3) 0.0727(19) Uani 1 1 d . . . . .
H29 H 0.3447 0.1789 0.9386 0.087 Uiso 1 1 calc R U . . .
C30 C 0.2770(3) 0.1811(5) 0.8239(3) 0.0552(16) Uani 1 1 d . . . . .
H30 H 0.2428 0.1004 0.8223 0.066 Uiso 1 1 calc R U . . .
C31 C 0.1282(3) 0.1542(5) 0.6757(3) 0.0439(14) Uani 1 1 d . . . . .
C32 C 0.0925(3) 0.2154(5) 0.7215(3) 0.0549(16) Uani 1 1 d . . . . .
H32 H 0.1194 0.2903 0.7584 0.066 Uiso 1 1 calc R U . . .
C33 C 0.0168(4) 0.1625(6) 0.7109(4) 0.0727(19) Uani 1 1 d . . . . .
H33 H -0.0068 0.2036 0.7410 0.087 Uiso 1 1 calc R U . . .
C34 C -0.0244(4) 0.0511(6) 0.6572(4) 0.079(2) Uani 1 1 d . . . . .
H34 H -0.0752 0.0172 0.6509 0.094 Uiso 1 1 calc R U . . .
C35 C 0.0111(3) -0.0099(6) 0.6125(3) 0.0696(19) Uani 1 1 d . . . . .
H35 H -0.0160 -0.0844 0.5754 0.084 Uiso 1 1 calc R U . . .
C36 C 0.0864(3) 0.0403(5) 0.6233(3) 0.0522(16) Uani 1 1 d . . . . .
H36 H 0.1103 -0.0041 0.5942 0.063 Uiso 1 1 calc R U . . .
N1 N 0.2048(3) 0.2089(4) 0.6849(2) 0.0477(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.218(5) . ?
C1 C9 1.496(6) . ?
C1 C2 1.505(6) . ?
C2 C3 1.346(6) . ?
C2 C10 1.475(6) . ?
C3 C13 1.462(6) . ?
C3 C4 1.495(6) . ?
C4 C5 1.374(5) . ?
C4 C9 1.384(6) . ?
C5 C6 1.403(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.397(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.410(5) . ?
C7 C19 1.485(6) . ?
C8 C9 1.370(6) . ?
C8 H8 0.9300 . ?
C10 O2 1.190(5) . ?
C10 O3 1.330(5) . ?
O3 C11 1.458(5) . ?
C11 C12 1.466(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.379(6) . ?
C13 C14 1.386(6) . ?
C14 C15 1.382(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.396(5) . ?
C19 C20 1.405(5) . ?
C20 C21 1.377(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.395(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.382(6) . ?
C22 N1 1.436(5) . ?
C23 C24 1.382(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.377(6) . ?
C25 C30 1.388(6) . ?
C25 N1 1.412(6) . ?
C26 C27 1.389(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.369(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.386(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.383(6) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C36 1.380(6) . ?
C31 C32 1.411(6) . ?
C31 N1 1.415(5) . ?
C32 C33 1.388(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.376(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.391(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.371(6) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C9 127.5(5) . . ?
O1 C1 C2 127.7(5) . . ?
C9 C1 C2 104.8(4) . . ?
C3 C2 C10 129.6(5) . . ?
C3 C2 C1 109.5(5) . . ?
C10 C2 C1 120.9(4) . . ?
C2 C3 C13 127.8(5) . . ?
C2 C3 C4 108.8(4) . . ?
C13 C3 C4 123.2(4) . . ?
C5 C4 C9 119.7(5) . . ?
C5 C4 C3 131.4(5) . . ?
C9 C4 C3 108.9(4) . . ?
C4 C5 C6 118.3(5) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C7 C6 C5 122.4(4) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C6 C7 C8 117.8(4) . . ?
C6 C7 C19 119.8(4) . . ?
C8 C7 C19 122.4(4) . . ?
C9 C8 C7 118.9(4) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C4 122.9(5) . . ?
C8 C9 C1 129.1(5) . . ?
C4 C9 C1 107.9(4) . . ?
O2 C10 O3 122.9(5) . . ?
O2 C10 C2 124.7(5) . . ?
O3 C10 C2 112.3(5) . . ?
C10 O3 C11 116.0(4) . . ?
O3 C11 C12 112.2(4) . . ?
O3 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
O3 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 118.6(5) . . ?
C18 C13 C3 121.1(5) . . ?
C14 C13 C3 120.3(5) . . ?
C15 C14 C13 120.2(6) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.7(6) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.4(6) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.6(6) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 120.5(5) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C24 C19 C20 116.2(4) . . ?
C24 C19 C7 123.0(4) . . ?
C20 C19 C7 120.8(4) . . ?
C21 C20 C19 121.7(4) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 120.7(5) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 118.7(5) . . ?
C23 C22 N1 121.6(5) . . ?
C21 C22 N1 119.7(5) . . ?
C24 C23 C22 120.2(5) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C19 122.5(5) . . ?
C23 C24 H24 118.8 . . ?
C19 C24 H24 118.8 . . ?
C26 C25 C30 119.3(5) . . ?
C26 C25 N1 120.3(5) . . ?
C30 C25 N1 120.3(5) . . ?
C25 C26 C27 120.6(5) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C28 C27 C26 120.5(6) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 118.8(6) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 H28 120.6 . . ?
C30 C29 C28 121.3(6) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C29 C30 C25 119.4(5) . . ?
C29 C30 H30 120.3 . . ?
C25 C30 H30 120.3 . . ?
C36 C31 C32 117.8(5) . . ?
C36 C31 N1 122.3(5) . . ?
C32 C31 N1 119.9(5) . . ?
C33 C32 C31 119.3(5) . . ?
C33 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
C34 C33 C32 121.8(6) . . ?
C34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C33 C34 C35 118.8(6) . . ?
C33 C34 H34 120.6 . . ?
C35 C34 H34 120.6 . . ?
C36 C35 C34 119.7(6) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C35 C36 C31 122.5(5) . . ?
C35 C36 H36 118.7 . . ?
C31 C36 H36 118.7 . . ?
C25 N1 C31 123.3(4) . . ?
C25 N1 C22 118.2(4) . . ?
C31 N1 C22 118.5(4) . . ?

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 C3 -178.2(5) . . . . ?
C9 C1 C2 C3 2.3(5) . . . . ?
O1 C1 C2 C10 0.1(8) . . . . ?
C9 C1 C2 C10 -179.4(4) . . . . ?
C10 C2 C3 C13 -4.7(8) . . . . ?
C1 C2 C3 C13 173.5(4) . . . . ?
C10 C2 C3 C4 -179.8(4) . . . . ?
C1 C2 C3 C4 -1.7(5) . . . . ?
C2 C3 C4 C5 178.0(4) . . . . ?
C13 C3 C4 C5 2.5(8) . . . . ?
C2 C3 C4 C9 0.3(6) . . . . ?
C13 C3 C4 C9 -175.1(4) . . . . ?
C9 C4 C5 C6 -2.0(7) . . . . ?
C3 C4 C5 C6 -179.4(4) . . . . ?
C4 C5 C6 C7 1.9(7) . . . . ?
C5 C6 C7 C8 0.3(7) . . . . ?
C5 C6 C7 C19 179.4(4) . . . . ?
C6 C7 C8 C9 -2.4(6) . . . . ?
C19 C7 C8 C9 178.5(4) . . . . ?
C7 C8 C9 C4 2.4(7) . . . . ?
C7 C8 C9 C1 178.3(4) . . . . ?
C5 C4 C9 C8 -0.1(7) . . . . ?
C3 C4 C9 C8 177.9(4) . . . . ?
C5 C4 C9 C1 -176.8(4) . . . . ?
C3 C4 C9 C1 1.2(5) . . . . ?
O1 C1 C9 C8 2.1(8) . . . . ?
C2 C1 C9 C8 -178.5(5) . . . . ?
O1 C1 C9 C4 178.5(5) . . . . ?
C2 C1 C9 C4 -2.1(5) . . . . ?
C3 C2 C10 O2 142.3(6) . . . . ?
C1 C2 C10 O2 -35.6(8) . . . . ?
C3 C2 C10 O3 -41.4(7) . . . . ?
C1 C2 C10 O3 140.7(4) . . . . ?
O2 C10 O3 C11 -5.5(8) . . . . ?
C2 C10 O3 C11 178.1(4) . . . . ?
C10 O3 C11 C12 -83.0(6) . . . . ?
C2 C3 C13 C18 131.4(5) . . . . ?
C4 C3 C13 C18 -54.1(7) . . . . ?
C2 C3 C13 C14 -49.5(7) . . . . ?
C4 C3 C13 C14 125.1(5) . . . . ?
C18 C13 C14 C15 0.0(8) . . . . ?
C3 C13 C14 C15 -179.2(5) . . . . ?
C13 C14 C15 C16 -0.7(9) . . . . ?
C14 C15 C16 C17 0.7(10) . . . . ?
C15 C16 C17 C18 -0.1(10) . . . . ?
C14 C13 C18 C17 0.6(8) . . . . ?
C3 C13 C18 C17 179.8(4) . . . . ?
C16 C17 C18 C13 -0.6(8) . . . . ?
C6 C7 C19 C24 6.5(7) . . . . ?
C8 C7 C19 C24 -174.4(4) . . . . ?
C6 C7 C19 C20 -173.7(4) . . . . ?
C8 C7 C19 C20 5.4(7) . . . . ?
C24 C19 C20 C21 -0.1(7) . . . . ?
C7 C19 C20 C21 -179.9(4) . . . . ?
C19 C20 C21 C22 -0.3(7) . . . . ?
C20 C21 C22 C23 -0.1(7) . . . . ?
C20 C21 C22 N1 -179.6(4) . . . . ?
C21 C22 C23 C24 1.0(7) . . . . ?
N1 C22 C23 C24 -179.5(4) . . . . ?
C22 C23 C24 C19 -1.4(7) . . . . ?
C20 C19 C24 C23 0.9(7) . . . . ?
C7 C19 C24 C23 -179.2(4) . . . . ?
C30 C25 C26 C27 1.7(7) . . . . ?
N1 C25 C26 C27 -177.6(4) . . . . ?
C25 C26 C27 C28 -2.4(8) . . . . ?
C26 C27 C28 C29 1.2(9) . . . . ?
C27 C28 C29 C30 0.5(9) . . . . ?
C28 C29 C30 C25 -1.1(8) . . . . ?
C26 C25 C30 C29 0.0(8) . . . . ?
N1 C25 C30 C29 179.4(4) . . . . ?
C36 C31 C32 C33 -1.7(7) . . . . ?
N1 C31 C32 C33 178.9(4) . . . . ?
C31 C32 C33 C34 0.4(8) . . . . ?
C32 C33 C34 C35 0.0(9) . . . . ?
C33 C34 C35 C36 0.8(9) . . . . ?
C34 C35 C36 C31 -2.2(8) . . . . ?
C32 C31 C36 C35 2.6(7) . . . . ?
N1 C31 C36 C35 -178.0(5) . . . . ?
C26 C25 N1 C31 -145.8(4) . . . . ?
C30 C25 N1 C31 34.8(7) . . . . ?
C26 C25 N1 C22 37.7(6) . . . . ?
C30 C25 N1 C22 -141.6(5) . . . . ?
C36 C31 N1 C25 -145.3(5) . . . . ?
C32 C31 N1 C25 34.1(7) . . . . ?
C36 C31 N1 C22 31.2(6) . . . . ?
C32 C31 N1 C22 -149.4(4) . . . . ?
C23 C22 N1 C25 -139.0(4) . . . . ?
C21 C22 N1 C25 40.5(6) . . . . ?
C23 C22 N1 C31 44.3(6) . . . . ?
C21 C22 N1 C31 -136.2(4) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.046


####################################################################### 
# 
# 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_VC1647
_database_code_depnum_ccdc_archive 'CCDC 1062837'
_audit_update_record             
;
2015-05-02 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
"ethyl 3-(4'-(diphenylamino)biphenyl-4-yl)-6-methoxy-1-oxo-1H-indene-2-carboxylate"
_chemical_formula_moiety         'C37 H29 N O4'
_chemical_formula_sum            'C37 H29 N O4'
_chemical_formula_weight         551.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.994(5)
_cell_length_b                   12.067(5)
_cell_length_c                   13.535(5)
_cell_angle_alpha                97.328(5)
_cell_angle_beta                 89.921(5)
_cell_angle_gamma                106.327(5)
_cell_volume                     1397.3(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1016
_cell_measurement_theta_min      2.1725
_cell_measurement_theta_max      29.1271


_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_min  0.55041
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.0827
_diffrn_reflns_number            11280
_diffrn_reflns_av_unetI/netI     0.2288
_diffrn_reflns_av_R_equivalents  0.0998
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.177
_diffrn_reflns_theta_max         29.191
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6309
_reflns_number_gt                2002
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6309
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2648
_refine_ls_R_factor_gt           0.0814
_refine_ls_wR_factor_ref         0.2064
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.955
_refine_ls_shift/su_max          0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.5870(6) 0.6784(4) -0.4422(3) 0.0529(14) Uani 1 1 d . . . . .
O1 O 1.7093(4) 0.7296(3) -0.4759(2) 0.0709(11) Uani 1 1 d . . . . .
C2 C 1.5628(5) 0.5902(4) -0.3710(3) 0.0494(13) Uani 1 1 d . . . . .
C3 C 1.4088(5) 0.5570(4) -0.3516(3) 0.0444(12) Uani 1 1 d . . . . .
C4 C 1.3251(5) 0.6190(4) -0.4097(3) 0.0439(12) Uani 1 1 d . . . . .
C5 C 1.1713(5) 0.6179(4) -0.4139(3) 0.0511(13) Uani 1 1 d . . . . .
H5 H 1.0983 0.5688 -0.3785 0.061 Uiso 1 1 calc R U . . .
C6 C 1.1271(5) 0.6913(4) -0.4718(3) 0.0572(14) Uani 1 1 d . . . . .
H6 H 1.0235 0.6903 -0.4758 0.069 Uiso 1 1 calc R U . . .
C7 C 1.2354(6) 0.7660(4) -0.5236(4) 0.0548(14) Uani 1 1 d . . . . .
C8 C 1.3895(6) 0.7682(4) -0.5191(3) 0.0511(13) Uani 1 1 d . . . . .
H8 H 1.4633 0.8189 -0.5528 0.061 Uiso 1 1 calc R U . . .
C9 C 1.4305(5) 0.6935(4) -0.4637(3) 0.0469(13) Uani 1 1 d . . . . .
C10 C 1.6906(6) 0.5546(4) -0.3300(4) 0.0529(14) Uani 1 1 d . . . . .
O2 O 1.8242(4) 0.6060(3) -0.3349(3) 0.0987(15) Uani 1 1 d . . . . .
O3 O 1.6422(3) 0.4596(3) -0.2858(2) 0.0594(10) Uani 1 1 d . . . . .
C11 C 1.7588(5) 0.4215(4) -0.2392(4) 0.0649(15) Uani 1 1 d . . . . .
H11A H 1.8307 0.4871 -0.1992 0.078 Uiso 1 1 calc R U . . .
H11B H 1.8165 0.3884 -0.2895 0.078 Uiso 1 1 calc R U . . .
C12 C 1.6822(6) 0.3332(5) -0.1754(4) 0.101(2) Uani 1 1 d . . . . .
H12A H 1.6234 0.3661 -0.1267 0.151 Uiso 1 1 calc R U . . .
H12B H 1.7593 0.3086 -0.1421 0.151 Uiso 1 1 calc R U . . .
H12C H 1.6142 0.2673 -0.2158 0.151 Uiso 1 1 calc R U . . .
O4 O 1.1767(4) 0.8336(3) -0.5777(3) 0.0719(11) Uani 1 1 d . . . . .
C13 C 1.2819(6) 0.9280(4) -0.6156(4) 0.092(2) Uani 1 1 d . . . . .
H13A H 1.3444 0.9792 -0.5617 0.138 Uiso 1 1 calc R U . . .
H13B H 1.2252 0.9698 -0.6490 0.138 Uiso 1 1 calc R U . . .
H13C H 1.3474 0.8990 -0.6619 0.138 Uiso 1 1 calc R U . . .
C14 C 1.3256(5) 0.4833(4) -0.2781(3) 0.0387(11) Uani 1 1 d . . . . .
C15 C 1.3685(5) 0.5110(4) -0.1776(3) 0.0503(14) Uani 1 1 d . . . . .
H15 H 1.4558 0.5725 -0.1571 0.060 Uiso 1 1 calc R U . . .
C16 C 1.2838(5) 0.4489(4) -0.1077(3) 0.0518(14) Uani 1 1 d . . . . .
H16 H 1.3151 0.4694 -0.0408 0.062 Uiso 1 1 calc R U . . .
C17 C 1.1524(5) 0.3560(4) -0.1348(3) 0.0412(12) Uani 1 1 d . . . . .
C18 C 1.1141(5) 0.3261(4) -0.2360(4) 0.0493(13) Uani 1 1 d . . . . .
H18 H 1.0309 0.2615 -0.2571 0.059 Uiso 1 1 calc R U . . .
C19 C 1.1967(5) 0.3901(4) -0.3060(3) 0.0464(12) Uani 1 1 d . . . . .
H19 H 1.1651 0.3702 -0.3729 0.056 Uiso 1 1 calc R U . . .
C20 C 1.0528(5) 0.2918(4) -0.0618(3) 0.0406(12) Uani 1 1 d . . . . .
C21 C 1.0139(5) 0.3539(4) 0.0228(3) 0.0505(13) Uani 1 1 d . . . . .
H21 H 1.0596 0.4338 0.0358 0.061 Uiso 1 1 calc R U . . .
C22 C 0.9077(5) 0.2989(4) 0.0888(3) 0.0520(13) Uani 1 1 d . . . . .
H22 H 0.8815 0.3422 0.1445 0.062 Uiso 1 1 calc R U . . .
C23 C 0.8419(5) 0.1805(4) 0.0713(3) 0.0465(13) Uani 1 1 d . . . . .
C24 C 0.8850(5) 0.1167(4) -0.0098(3) 0.0507(13) Uani 1 1 d . . . . .
H24 H 0.8440 0.0361 -0.0201 0.061 Uiso 1 1 calc R U . . .
C25 C 0.9886(5) 0.1715(4) -0.0758(3) 0.0508(13) Uani 1 1 d . . . . .
H25 H 1.0158 0.1273 -0.1306 0.061 Uiso 1 1 calc R U . . .
N1 N 0.7256(4) 0.1250(3) 0.1360(3) 0.0549(12) Uani 1 1 d . . . . .
C26 C 0.7684(5) 0.0652(4) 0.2113(3) 0.0443(12) Uani 1 1 d . . . . .
C27 C 0.9031(5) 0.1148(4) 0.2675(4) 0.0558(14) Uani 1 1 d . . . . .
H27 H 0.9671 0.1873 0.2570 0.067 Uiso 1 1 calc R U . . .
C28 C 0.9428(6) 0.0557(5) 0.3401(4) 0.0647(15) Uani 1 1 d . . . . .
H28 H 1.0333 0.0902 0.3787 0.078 Uiso 1 1 calc R U . . .
C29 C 0.8517(6) -0.0528(5) 0.3567(4) 0.0672(16) Uani 1 1 d . . . . .
H29 H 0.8788 -0.0913 0.4061 0.081 Uiso 1 1 calc R U . . .
C30 C 0.7190(6) -0.1021(4) 0.2972(4) 0.0627(16) Uani 1 1 d . . . . .
H30 H 0.6571 -0.1759 0.3058 0.075 Uiso 1 1 calc R U . . .
C31 C 0.6759(5) -0.0446(4) 0.2254(3) 0.0505(13) Uani 1 1 d . . . . .
H31 H 0.5855 -0.0791 0.1866 0.061 Uiso 1 1 calc R U . . .
C32 C 0.5795(5) 0.1439(4) 0.1317(3) 0.0447(13) Uani 1 1 d . . . . .
C33 C 0.5261(5) 0.1743(4) 0.0452(4) 0.0554(14) Uani 1 1 d . . . . .
H33 H 0.5865 0.1780 -0.0108 0.066 Uiso 1 1 calc R U . . .
C34 C 0.3848(6) 0.1992(4) 0.0409(4) 0.0604(15) Uani 1 1 d . . . . .
H34 H 0.3523 0.2204 -0.0173 0.072 Uiso 1 1 calc R U . . .
C35 C 0.2924(5) 0.1927(4) 0.1228(4) 0.0580(14) Uani 1 1 d . . . . .
H35 H 0.1980 0.2099 0.1206 0.070 Uiso 1 1 calc R U . . .
C36 C 0.3425(5) 0.1602(4) 0.2072(4) 0.0573(14) Uani 1 1 d . . . . .
H36 H 0.2791 0.1533 0.2618 0.069 Uiso 1 1 calc R U . . .
C37 C 0.4848(5) 0.1375(4) 0.2139(3) 0.0520(13) Uani 1 1 d . . . . .
H37 H 0.5170 0.1180 0.2729 0.062 Uiso 1 1 calc R U . . .


_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 1.220(4) . ?
C1 C2 1.496(6) . ?
C1 C9 1.503(6) . ?
C2 C3 1.364(5) . ?
C2 C10 1.468(6) . ?
C3 C14 1.481(5) . ?
C3 C4 1.487(6) . ?
C4 C5 1.381(6) . ?
C4 C9 1.389(5) . ?
C5 C6 1.390(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(5) . ?
C6 H6 0.9300 . ?
C7 O4 1.370(5) . ?
C7 C8 1.380(6) . ?
C8 C9 1.367(6) . ?
C8 H8 0.9300 . ?
C10 O2 1.193(5) . ?
C10 O3 1.324(5) . ?
O3 C11 1.434(5) . ?
C11 C12 1.476(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O4 C13 1.413(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.382(5) . ?
C14 C15 1.387(5) . ?
C15 C16 1.377(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.390(6) . ?
C17 C20 1.477(5) . ?
C18 C19 1.382(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.386(6) . ?
C20 C25 1.391(5) . ?
C21 C22 1.394(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.373(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(6) . ?
C23 N1 1.436(5) . ?
C24 C25 1.381(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N1 C32 1.398(5) . ?
N1 C26 1.434(5) . ?
C26 C27 1.372(6) . ?
C26 C31 1.388(5) . ?
C27 C28 1.387(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.381(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.382(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.378(6) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C33 1.395(6) . ?
C32 C37 1.397(5) . ?
C33 C34 1.389(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.381(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.370(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.388(6) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 127.3(5) . . ?
O1 C1 C9 126.1(4) . . ?
C2 C1 C9 106.6(4) . . ?
C3 C2 C10 129.4(4) . . ?
C3 C2 C1 107.8(4) . . ?
C10 C2 C1 122.8(4) . . ?
C2 C3 C14 130.1(4) . . ?
C2 C3 C4 109.6(4) . . ?
C14 C3 C4 119.9(4) . . ?
C5 C4 C9 118.7(4) . . ?
C5 C4 C3 131.9(4) . . ?
C9 C4 C3 109.3(4) . . ?
C4 C5 C6 119.1(4) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 120.9(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O4 C7 C8 124.7(4) . . ?
O4 C7 C6 115.0(4) . . ?
C8 C7 C6 120.4(5) . . ?
C9 C8 C7 118.0(4) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C8 C9 C4 122.9(5) . . ?
C8 C9 C1 130.3(4) . . ?
C4 C9 C1 106.6(4) . . ?
O2 C10 O3 123.3(5) . . ?
O2 C10 C2 123.8(5) . . ?
O3 C10 C2 112.9(4) . . ?
C10 O3 C11 116.8(4) . . ?
O3 C11 C12 108.6(4) . . ?
O3 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
O3 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 O4 C13 118.2(4) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 117.9(4) . . ?
C19 C14 C3 121.3(4) . . ?
C15 C14 C3 120.6(4) . . ?
C16 C15 C14 121.0(4) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 121.6(4) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 116.9(4) . . ?
C18 C17 C20 119.8(4) . . ?
C16 C17 C20 123.3(4) . . ?
C19 C18 C17 121.6(4) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C14 121.0(4) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C21 C20 C25 117.7(4) . . ?
C21 C20 C17 119.0(4) . . ?
C25 C20 C17 123.2(4) . . ?
C20 C21 C22 121.4(4) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 119.7(4) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 119.6(4) . . ?
C22 C23 N1 119.7(5) . . ?
C24 C23 N1 120.7(4) . . ?
C23 C24 C25 120.5(4) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 121.0(4) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?
C32 N1 C26 121.9(3) . . ?
C32 N1 C23 118.5(4) . . ?
C26 N1 C23 119.1(4) . . ?
C27 C26 C31 120.0(5) . . ?
C27 C26 N1 120.0(4) . . ?
C31 C26 N1 120.0(4) . . ?
C26 C27 C28 119.3(4) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C29 C28 C27 121.9(5) . . ?
C29 C28 H28 119.0 . . ?
C27 C28 H28 119.0 . . ?
C30 C29 C28 117.5(5) . . ?
C30 C29 H29 121.2 . . ?
C28 C29 H29 121.2 . . ?
C31 C30 C29 121.7(5) . . ?
C31 C30 H30 119.1 . . ?
C29 C30 H30 119.1 . . ?
C30 C31 C26 119.5(5) . . ?
C30 C31 H31 120.2 . . ?
C26 C31 H31 120.2 . . ?
C33 C32 C37 117.7(4) . . ?
C33 C32 N1 120.4(4) . . ?
C37 C32 N1 121.8(4) . . ?
C34 C33 C32 121.4(4) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C35 C34 C33 120.2(5) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C36 C35 C34 118.7(5) . . ?
C36 C35 H35 120.7 . . ?
C34 C35 H35 120.7 . . ?
C35 C36 C37 122.1(5) . . ?
C35 C36 H36 119.0 . . ?
C37 C36 H36 119.0 . . ?
C36 C37 C32 119.9(5) . . ?
C36 C37 H37 120.1 . . ?
C32 C37 H37 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.9(5) . . . . ?
C9 C1 C2 C3 -0.4(5) . . . . ?
O1 C1 C2 C10 1.1(8) . . . . ?
C9 C1 C2 C10 -178.1(4) . . . . ?
C10 C2 C3 C14 5.6(9) . . . . ?
C1 C2 C3 C14 -171.9(4) . . . . ?
C10 C2 C3 C4 178.6(5) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C2 C3 C4 C5 -178.0(5) . . . . ?
C14 C3 C4 C5 -4.2(8) . . . . ?
C2 C3 C4 C9 -1.5(5) . . . . ?
C14 C3 C4 C9 172.4(4) . . . . ?
C9 C4 C5 C6 0.0(7) . . . . ?
C3 C4 C5 C6 176.3(5) . . . . ?
C4 C5 C6 C7 -1.0(7) . . . . ?
C5 C6 C7 O4 -179.9(4) . . . . ?
C5 C6 C7 C8 0.4(8) . . . . ?
O4 C7 C8 C9 -178.6(4) . . . . ?
C6 C7 C8 C9 1.1(7) . . . . ?
C7 C8 C9 C4 -2.1(7) . . . . ?
C7 C8 C9 C1 -177.9(5) . . . . ?
C5 C4 C9 C8 1.6(7) . . . . ?
C3 C4 C9 C8 -175.5(4) . . . . ?
C5 C4 C9 C1 178.2(4) . . . . ?
C3 C4 C9 C1 1.1(5) . . . . ?
O1 C1 C9 C8 -3.5(9) . . . . ?
C2 C1 C9 C8 175.8(5) . . . . ?
O1 C1 C9 C4 -179.8(4) . . . . ?
C2 C1 C9 C4 -0.5(5) . . . . ?
C3 C2 C10 O2 -163.3(5) . . . . ?
C1 C2 C10 O2 13.9(8) . . . . ?
C3 C2 C10 O3 16.0(8) . . . . ?
C1 C2 C10 O3 -166.8(4) . . . . ?
O2 C10 O3 C11 2.3(7) . . . . ?
C2 C10 O3 C11 -177.0(4) . . . . ?
C10 O3 C11 C12 167.1(4) . . . . ?
C8 C7 O4 C13 -13.1(7) . . . . ?
C6 C7 O4 C13 167.2(4) . . . . ?
C2 C3 C14 C19 -129.0(5) . . . . ?
C4 C3 C14 C19 58.5(6) . . . . ?
C2 C3 C14 C15 55.7(7) . . . . ?
C4 C3 C14 C15 -116.8(5) . . . . ?
C19 C14 C15 C16 -1.0(7) . . . . ?
C3 C14 C15 C16 174.4(4) . . . . ?
C14 C15 C16 C17 0.1(8) . . . . ?
C15 C16 C17 C18 2.4(7) . . . . ?
C15 C16 C17 C20 -176.1(4) . . . . ?
C16 C17 C18 C19 -4.0(7) . . . . ?
C20 C17 C18 C19 174.5(4) . . . . ?
C17 C18 C19 C14 3.2(7) . . . . ?
C15 C14 C19 C18 -0.6(7) . . . . ?
C3 C14 C19 C18 -176.0(4) . . . . ?
C18 C17 C20 C21 -134.9(5) . . . . ?
C16 C17 C20 C21 43.4(7) . . . . ?
C18 C17 C20 C25 41.6(7) . . . . ?
C16 C17 C20 C25 -140.0(5) . . . . ?
C25 C20 C21 C22 -3.4(7) . . . . ?
C17 C20 C21 C22 173.3(4) . . . . ?
C20 C21 C22 C23 1.3(7) . . . . ?
C21 C22 C23 C24 1.9(7) . . . . ?
C21 C22 C23 N1 -176.2(4) . . . . ?
C22 C23 C24 C25 -2.9(7) . . . . ?
N1 C23 C24 C25 175.3(4) . . . . ?
C23 C24 C25 C20 0.6(7) . . . . ?
C21 C20 C25 C24 2.5(7) . . . . ?
C17 C20 C25 C24 -174.1(4) . . . . ?
C22 C23 N1 C32 70.8(6) . . . . ?
C24 C23 N1 C32 -107.3(5) . . . . ?
C22 C23 N1 C26 -101.0(5) . . . . ?
C24 C23 N1 C26 80.8(6) . . . . ?
C32 N1 C26 C27 -128.0(5) . . . . ?
C23 N1 C26 C27 43.6(6) . . . . ?
C32 N1 C26 C31 54.0(6) . . . . ?
C23 N1 C26 C31 -134.4(5) . . . . ?
C31 C26 C27 C28 -2.0(7) . . . . ?
N1 C26 C27 C28 180.0(4) . . . . ?
C26 C27 C28 C29 1.0(7) . . . . ?
C27 C28 C29 C30 0.8(7) . . . . ?
C28 C29 C30 C31 -1.6(7) . . . . ?
C29 C30 C31 C26 0.6(7) . . . . ?
C27 C26 C31 C30 1.2(7) . . . . ?
N1 C26 C31 C30 179.2(4) . . . . ?
C26 N1 C32 C33 -163.4(4) . . . . ?
C23 N1 C32 C33 25.0(7) . . . . ?
C26 N1 C32 C37 19.1(7) . . . . ?
C23 N1 C32 C37 -152.6(4) . . . . ?
C37 C32 C33 C34 1.0(7) . . . . ?
N1 C32 C33 C34 -176.7(4) . . . . ?
C32 C33 C34 C35 -0.9(8) . . . . ?
C33 C34 C35 C36 -0.6(8) . . . . ?
C34 C35 C36 C37 2.1(8) . . . . ?
C35 C36 C37 C32 -2.0(8) . . . . ?
C33 C32 C37 C36 0.5(7) . . . . ?
N1 C32 C37 C36 178.1(4) . . . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.061


