# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_22
_database_code_depnum_ccdc_archive 'CCDC 1432547'
_audit_update_record             
;
2016-02-21 deposited with the CCDC.
2016-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'(S)-tert-butyl 3-(2-(4-chlorophenyl)-2-oxoethyl)-2-oxo-3-(10-oxo-9,10-dihydroanthr acen-9-yl)indoline-1-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          395
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H28 Cl N O5'
_chemical_formula_weight         578.03

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   9.6372(4)
_cell_length_b                   15.6851(7)
_cell_length_c                   9.8491(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.7964(11)
_cell_angle_gamma                90
_cell_volume                     1462.44(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.355
_exptl_crystal_size_min          0.186
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23252
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.009
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6730
_reflns_number_gt                5357
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.996

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1600P)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_abs_structure_details 
;
 Flack x determined using 2028 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(4)
_chemical_absolute_configuration UNK
_refine_ls_number_reflns         6730
_refine_ls_number_parameters     382
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0824
_refine_ls_wR_factor_ref         0.2394
_refine_ls_wR_factor_gt          0.2112
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
Cl1 Cl 1.73550(17) 1.24480(13) 0.8483(2) 0.0772(6) Uani 1 1 d . . . . .
O1 O 0.8069(4) 1.0881(2) 0.5648(4) 0.0454(9) Uani 1 1 d . . . . .
O2 O 0.6847(5) 0.9955(3) 0.3546(5) 0.0606(12) Uani 1 1 d . . . . .
O3 O 0.7403(6) 0.8567(3) 0.3555(6) 0.0772(18) Uani 1 1 d . . . . .
O4 O 1.1307(5) 1.0621(4) 0.5566(4) 0.0646(14) Uani 1 1 d . . . . .
O5 O 0.9160(6) 0.7586(3) 1.0042(5) 0.0634(12) Uani 1 1 d . . . . .
N1 N 0.8578(4) 0.9463(2) 0.5194(4) 0.0357(8) Uani 1 1 d . . . . .
C2 C 0.8671(5) 1.0227(3) 0.5972(5) 0.0336(9) Uani 1 1 d . . . . .
C1 C 0.9619(5) 1.0045(3) 0.7375(5) 0.0342(9) Uani 1 1 d . . . . .
C4 C 1.0225(5) 0.9181(3) 0.7148(5) 0.0348(9) Uani 1 1 d . . . . .
C3 C 0.9545(5) 0.8851(3) 0.5885(5) 0.0358(9) Uani 1 1 d . . . . .
C5 C 1.1263(6) 0.8712(4) 0.7982(6) 0.0449(11) Uani 1 1 d . . . . .
H5 H 1.1722 0.8927 0.8827 0.054 Uiso 1 1 calc R U . . .
C7 C 1.0899(8) 0.7580(4) 0.6297(7) 0.0612(16) Uani 1 1 d . . . . .
H7 H 1.1126 0.7036 0.6032 0.073 Uiso 1 1 calc R U . . .
C8 C 0.9870(7) 0.8045(4) 0.5462(6) 0.0525(13) Uani 1 1 d . . . . .
H8 H 0.9400 0.7823 0.4627 0.063 Uiso 1 1 calc R U . . .
C6 C 1.1603(8) 0.7925(5) 0.7541(7) 0.0635(17) Uani 1 1 d . . . . .
H6 H 1.2321 0.7613 0.8084 0.076 Uiso 1 1 calc R U . . .
C9 C 1.0709(6) 1.0750(3) 0.7774(5) 0.0429(11) Uani 1 1 d . . . . .
H9A H 1.0221 1.1277 0.7898 0.051 Uiso 1 1 calc R U . . .
H9B H 1.1302 1.0607 0.8653 0.051 Uiso 1 1 calc R U . . .
C14 C 1.5640(6) 1.2061(4) 0.7947(7) 0.0482(12) Uani 1 1 d . . . . .
C15 C 1.5223(7) 1.1803(4) 0.6613(7) 0.0559(15) Uani 1 1 d . . . . .
H15 H 1.5823 1.1865 0.5981 0.067 Uiso 1 1 calc R U . . .
C10 C 1.1636(6) 1.0893(3) 0.6717(5) 0.0409(10) Uani 1 1 d . . . . .
C12 C 1.3441(7) 1.1661(4) 0.8489(6) 0.0534(14) Uani 1 1 d . . . . .
H12 H 1.2831 1.1630 0.9116 0.064 Uiso 1 1 calc R U . . .
C13 C 1.4760(8) 1.2020(4) 0.8890(7) 0.0588(16) Uani 1 1 d . . . . .
H13 H 1.5047 1.2229 0.9782 0.071 Uiso 1 1 calc R U . . .
C16 C 1.3889(6) 1.1447(4) 0.6207(6) 0.0496(13) Uani 1 1 d . . . . .
H16 H 1.3585 1.1277 0.5295 0.060 Uiso 1 1 calc R U . . .
C11 C 1.3013(5) 1.1345(3) 0.7158(5) 0.0364(10) Uani 1 1 d . . . . .
C18 C 0.9333(5) 0.9885(3) 0.9923(5) 0.0356(9) Uani 1 1 d . . . . .
C17 C 0.8556(5) 1.0013(3) 0.8452(5) 0.0336(9) Uani 1 1 d . . . . .
H17 H 0.8082 1.0567 0.8415 0.040 Uiso 1 1 calc R U . . .
C23 C 0.9498(5) 0.9058(3) 1.0466(5) 0.0384(10) Uani 1 1 d . . . . .
C19 C 0.9862(6) 1.0573(4) 1.0755(6) 0.0465(12) Uani 1 1 d . . . . .
H19 H 0.9774 1.1123 1.0394 0.056 Uiso 1 1 calc R U . . .
C24 C 0.8838(6) 0.8321(3) 0.9684(6) 0.0434(12) Uani 1 1 d . . . . .
C22 C 1.0176(6) 0.8944(4) 1.1840(5) 0.0491(13) Uani 1 1 d . . . . .
H22 H 1.0289 0.8396 1.2207 0.059 Uiso 1 1 calc R U . . .
C21 C 1.0682(7) 0.9638(5) 1.2666(6) 0.0592(16) Uani 1 1 d . . . . .
H21 H 1.1127 0.9555 1.3579 0.071 Uiso 1 1 calc R U . . .
C20 C 1.0521(7) 1.0446(5) 1.2124(6) 0.0595(16) Uani 1 1 d . . . . .
H20 H 1.0855 1.0912 1.2674 0.071 Uiso 1 1 calc R U . . .
C25 C 0.7647(6) 0.8516(3) 0.8525(6) 0.0419(11) Uani 1 1 d . . . . .
C30 C 0.7431(5) 0.9348(3) 0.8029(5) 0.0366(9) Uani 1 1 d . . . . .
C29 C 0.6194(6) 0.9537(4) 0.7122(6) 0.0547(14) Uani 1 1 d . . . . .
H29 H 0.6035 1.0090 0.6789 0.066 Uiso 1 1 calc R U . . .
C27 C 0.5443(8) 0.8078(6) 0.7148(8) 0.073(2) Uani 1 1 d . . . . .
H27 H 0.4786 0.7654 0.6833 0.088 Uiso 1 1 calc R U . . .
C26 C 0.6663(8) 0.7884(4) 0.8054(7) 0.0594(16) Uani 1 1 d . . . . .
H26 H 0.6835 0.7325 0.8356 0.071 Uiso 1 1 calc R U . . .
C28 C 0.5198(8) 0.8919(6) 0.6704(8) 0.073(2) Uani 1 1 d . . . . .
H28 H 0.4354 0.9062 0.6122 0.088 Uiso 1 1 calc R U . . .
C31 C 0.7560(6) 0.9273(3) 0.4003(6) 0.0416(10) Uani 1 1 d . . . . .
C32 C 0.5614(7) 0.9922(4) 0.2418(7) 0.0539(13) Uani 1 1 d . . . . .
C33 C 0.5997(10) 0.9557(10) 0.1150(8) 0.108(4) Uani 1 1 d . . . . .
H33A H 0.6701 0.9909 0.0856 0.162 Uiso 1 1 calc R U . . .
H33B H 0.5174 0.9534 0.0432 0.162 Uiso 1 1 calc R U . . .
H33C H 0.6366 0.8992 0.1341 0.162 Uiso 1 1 calc R U . . .
C34 C 0.4487(9) 0.9382(9) 0.2904(11) 0.104(3) Uani 1 1 d . . . . .
H34A H 0.4667 0.8790 0.2763 0.156 Uiso 1 1 calc R U . . .
H34B H 0.3574 0.9532 0.2387 0.156 Uiso 1 1 calc R U . . .
H34C H 0.4509 0.9484 0.3869 0.156 Uiso 1 1 calc R U . . .
C35 C 0.5128(13) 1.0820(6) 0.2294(11) 0.101(4) Uani 1 1 d . . . . .
H35A H 0.5057 1.1035 0.3190 0.152 Uiso 1 1 calc R U . . .
H35B H 0.4220 1.0849 0.1696 0.152 Uiso 1 1 calc R U . . .
H35C H 0.5794 1.1157 0.1914 0.152 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
Cl1 C14 1.747(5) . ?
O1 C2 1.192(6) . ?
O2 C31 1.305(7) . ?
O2 C32 1.468(7) . ?
O3 C31 1.191(7) . ?
O4 C10 1.197(6) . ?
O5 C24 1.227(6) . ?
N1 C31 1.413(6) . ?
N1 C2 1.416(6) . ?
N1 C3 1.420(6) . ?
C2 C1 1.534(7) . ?
C1 C4 1.510(6) . ?
C1 C9 1.525(6) . ?
C1 C17 1.607(6) . ?
C4 C5 1.381(7) . ?
C4 C3 1.393(7) . ?
C3 C8 1.384(7) . ?
C5 C6 1.369(9) . ?
C5 H5 0.9300 . ?
C7 C8 1.373(9) . ?
C7 C6 1.394(10) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C6 H6 0.9300 . ?
C9 C10 1.511(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C14 C15 1.362(9) . ?
C14 C13 1.371(10) . ?
C15 C16 1.390(8) . ?
C15 H15 0.9300 . ?
C10 C11 1.495(7) . ?
C12 C13 1.379(8) . ?
C12 C11 1.389(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C16 C11 1.382(7) . ?
C16 H16 0.9300 . ?
C18 C19 1.393(7) . ?
C18 C23 1.401(7) . ?
C18 C17 1.514(7) . ?
C17 C30 1.507(6) . ?
C17 H17 0.9800 . ?
C23 C22 1.400(7) . ?
C23 C24 1.467(8) . ?
C19 C20 1.393(8) . ?
C19 H19 0.9300 . ?
C24 C25 1.491(8) . ?
C22 C21 1.392(10) . ?
C22 H22 0.9300 . ?
C21 C20 1.373(11) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C25 C26 1.390(8) . ?
C25 C30 1.394(7) . ?
C30 C29 1.381(8) . ?
C29 C28 1.371(10) . ?
C29 H29 0.9300 . ?
C27 C26 1.371(11) . ?
C27 C28 1.397(13) . ?
C27 H27 0.9300 . ?
C26 H26 0.9300 . ?
C28 H28 0.9300 . ?
C32 C35 1.481(11) . ?
C32 C33 1.483(11) . ?
C32 C34 1.524(12) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 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
C31 O2 C32 122.1(5) . . ?
C31 N1 C2 126.3(4) . . ?
C31 N1 C3 123.1(4) . . ?
C2 N1 C3 110.1(4) . . ?
O1 C2 N1 127.3(4) . . ?
O1 C2 C1 125.4(4) . . ?
N1 C2 C1 107.3(4) . . ?
C4 C1 C9 115.0(4) . . ?
C4 C1 C2 102.4(4) . . ?
C9 C1 C2 111.3(4) . . ?
C4 C1 C17 112.4(3) . . ?
C9 C1 C17 110.3(4) . . ?
C2 C1 C17 104.8(4) . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 C1 130.3(5) . . ?
C3 C4 C1 109.7(4) . . ?
C8 C3 C4 120.8(5) . . ?
C8 C3 N1 129.7(5) . . ?
C4 C3 N1 109.4(4) . . ?
C6 C5 C4 118.8(6) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C8 C7 C6 119.9(6) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C3 118.9(6) . . ?
C7 C8 H8 120.5 . . ?
C3 C8 H8 120.5 . . ?
C5 C6 C7 121.5(6) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C10 C9 C1 113.4(4) . . ?
C10 C9 H9A 108.9 . . ?
C1 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C1 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C15 C14 C13 122.1(5) . . ?
C15 C14 Cl1 119.1(5) . . ?
C13 C14 Cl1 118.8(5) . . ?
C14 C15 C16 119.1(6) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
O4 C10 C11 120.5(5) . . ?
O4 C10 C9 120.9(5) . . ?
C11 C10 C9 118.5(4) . . ?
C13 C12 C11 120.7(6) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 118.6(6) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C11 C16 C15 120.1(5) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C11 C12 119.2(5) . . ?
C16 C11 C10 118.6(4) . . ?
C12 C11 C10 122.2(5) . . ?
C19 C18 C23 119.4(5) . . ?
C19 C18 C17 121.4(4) . . ?
C23 C18 C17 119.2(4) . . ?
C30 C17 C18 112.0(4) . . ?
C30 C17 C1 110.7(4) . . ?
C18 C17 C1 111.9(4) . . ?
C30 C17 H17 107.3 . . ?
C18 C17 H17 107.3 . . ?
C1 C17 H17 107.3 . . ?
C22 C23 C18 119.1(5) . . ?
C22 C23 C24 119.0(5) . . ?
C18 C23 C24 121.5(5) . . ?
C20 C19 C18 120.6(6) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
O5 C24 C23 121.8(6) . . ?
O5 C24 C25 122.0(5) . . ?
C23 C24 C25 115.8(4) . . ?
C21 C22 C23 120.9(6) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C20 C21 C22 119.6(5) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C20 C19 120.4(6) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C26 C25 C30 120.2(6) . . ?
C26 C25 C24 119.2(5) . . ?
C30 C25 C24 120.3(4) . . ?
C29 C30 C25 118.8(5) . . ?
C29 C30 C17 121.3(5) . . ?
C25 C30 C17 119.9(5) . . ?
C28 C29 C30 120.9(6) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C26 C27 C28 119.2(6) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C27 C26 C25 120.5(7) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C29 C28 C27 120.4(7) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
O3 C31 O2 127.7(5) . . ?
O3 C31 N1 121.6(5) . . ?
O2 C31 N1 110.6(4) . . ?
O2 C32 C35 103.2(6) . . ?
O2 C32 C33 110.9(6) . . ?
C35 C32 C33 115.0(9) . . ?
O2 C32 C34 107.8(6) . . ?
C35 C32 C34 108.8(9) . . ?
C33 C32 C34 110.8(9) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C31 N1 C2 O1 -12.9(8) . . . . ?
C3 N1 C2 O1 175.1(5) . . . . ?
C31 N1 C2 C1 163.1(5) . . . . ?
C3 N1 C2 C1 -8.8(5) . . . . ?
O1 C2 C1 C4 -173.4(5) . . . . ?
N1 C2 C1 C4 10.4(4) . . . . ?
O1 C2 C1 C9 -50.0(7) . . . . ?
N1 C2 C1 C9 133.8(4) . . . . ?
O1 C2 C1 C17 69.1(6) . . . . ?
N1 C2 C1 C17 -107.1(4) . . . . ?
C9 C1 C4 C5 51.7(7) . . . . ?
C2 C1 C4 C5 172.6(5) . . . . ?
C17 C1 C4 C5 -75.6(6) . . . . ?
C9 C1 C4 C3 -129.5(4) . . . . ?
C2 C1 C4 C3 -8.7(5) . . . . ?
C17 C1 C4 C3 103.2(4) . . . . ?
C5 C4 C3 C8 1.6(7) . . . . ?
C1 C4 C3 C8 -177.3(5) . . . . ?
C5 C4 C3 N1 -177.2(4) . . . . ?
C1 C4 C3 N1 3.9(5) . . . . ?
C31 N1 C3 C8 12.3(8) . . . . ?
C2 N1 C3 C8 -175.5(5) . . . . ?
C31 N1 C3 C4 -169.0(4) . . . . ?
C2 N1 C3 C4 3.2(5) . . . . ?
C3 C4 C5 C6 0.0(8) . . . . ?
C1 C4 C5 C6 178.6(6) . . . . ?
C6 C7 C8 C3 -0.5(10) . . . . ?
C4 C3 C8 C7 -1.4(9) . . . . ?
N1 C3 C8 C7 177.2(6) . . . . ?
C4 C5 C6 C7 -1.9(10) . . . . ?
C8 C7 C6 C5 2.2(11) . . . . ?
C4 C1 C9 C10 58.7(6) . . . . ?
C2 C1 C9 C10 -57.2(6) . . . . ?
C17 C1 C9 C10 -173.0(4) . . . . ?
C13 C14 C15 C16 -3.3(10) . . . . ?
Cl1 C14 C15 C16 176.1(5) . . . . ?
C1 C9 C10 O4 16.6(8) . . . . ?
C1 C9 C10 C11 -160.4(5) . . . . ?
C15 C14 C13 C12 3.7(11) . . . . ?
Cl1 C14 C13 C12 -175.6(5) . . . . ?
C11 C12 C13 C14 0.2(11) . . . . ?
C14 C15 C16 C11 -1.1(10) . . . . ?
C15 C16 C11 C12 4.8(9) . . . . ?
C15 C16 C11 C10 -174.9(6) . . . . ?
C13 C12 C11 C16 -4.4(10) . . . . ?
C13 C12 C11 C10 175.3(6) . . . . ?
O4 C10 C11 C16 0.5(9) . . . . ?
C9 C10 C11 C16 177.5(5) . . . . ?
O4 C10 C11 C12 -179.2(6) . . . . ?
C9 C10 C11 C12 -2.3(8) . . . . ?
C19 C18 C17 C30 -147.8(5) . . . . ?
C23 C18 C17 C30 30.9(6) . . . . ?
C19 C18 C17 C1 87.2(5) . . . . ?
C23 C18 C17 C1 -94.2(5) . . . . ?
C4 C1 C17 C30 -53.0(5) . . . . ?
C9 C1 C17 C30 177.2(4) . . . . ?
C2 C1 C17 C30 57.4(4) . . . . ?
C4 C1 C17 C18 72.7(5) . . . . ?
C9 C1 C17 C18 -57.1(5) . . . . ?
C2 C1 C17 C18 -176.9(4) . . . . ?
C19 C18 C23 C22 0.8(7) . . . . ?
C17 C18 C23 C22 -177.9(5) . . . . ?
C19 C18 C23 C24 173.7(5) . . . . ?
C17 C18 C23 C24 -5.0(7) . . . . ?
C23 C18 C19 C20 -1.4(8) . . . . ?
C17 C18 C19 C20 177.3(5) . . . . ?
C22 C23 C24 O5 -19.4(8) . . . . ?
C18 C23 C24 O5 167.6(5) . . . . ?
C22 C23 C24 C25 154.1(5) . . . . ?
C18 C23 C24 C25 -18.8(7) . . . . ?
C18 C23 C22 C21 0.1(8) . . . . ?
C24 C23 C22 C21 -173.0(5) . . . . ?
C23 C22 C21 C20 -0.3(9) . . . . ?
C22 C21 C20 C19 -0.3(9) . . . . ?
C18 C19 C20 C21 1.1(9) . . . . ?
O5 C24 C25 C26 15.9(9) . . . . ?
C23 C24 C25 C26 -157.6(5) . . . . ?
O5 C24 C25 C30 -171.5(5) . . . . ?
C23 C24 C25 C30 15.0(7) . . . . ?
C26 C25 C30 C29 3.2(8) . . . . ?
C24 C25 C30 C29 -169.3(5) . . . . ?
C26 C25 C30 C17 -174.9(5) . . . . ?
C24 C25 C30 C17 12.5(7) . . . . ?
C18 C17 C30 C29 147.1(5) . . . . ?
C1 C17 C30 C29 -87.2(6) . . . . ?
C18 C17 C30 C25 -34.8(6) . . . . ?
C1 C17 C30 C25 90.9(5) . . . . ?
C25 C30 C29 C28 -0.5(9) . . . . ?
C17 C30 C29 C28 177.7(6) . . . . ?
C28 C27 C26 C25 -0.1(12) . . . . ?
C30 C25 C26 C27 -3.0(10) . . . . ?
C24 C25 C26 C27 169.7(6) . . . . ?
C30 C29 C28 C27 -2.6(12) . . . . ?
C26 C27 C28 C29 2.9(13) . . . . ?
C32 O2 C31 O3 5.2(11) . . . . ?
C32 O2 C31 N1 -172.7(5) . . . . ?
C2 N1 C31 O3 -166.6(6) . . . . ?
C3 N1 C31 O3 4.4(9) . . . . ?
C2 N1 C31 O2 11.5(7) . . . . ?
C3 N1 C31 O2 -177.5(5) . . . . ?
C31 O2 C32 C35 178.0(8) . . . . ?
C31 O2 C32 C33 -58.5(10) . . . . ?
C31 O2 C32 C34 62.9(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C34 H34A Cl1 0.96 2.97 3.648(13) 128.5 2_746
C33 H33C O3 0.96 2.32 2.942(12) 121.9 .
C8 H8 O3 0.93 2.33 2.860(8) 116.0 .

_refine_diff_density_max         0.629
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.088

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate/n-hexane'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1432612'
_audit_update_record             
;
2015-10-22 deposited with the CCDC.
2016-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'(R)-tert-butyl 4-chloro-2-oxo-3-((S)-2-oxo-1-(10-oxo-9,10-dihydroanthracen-9-yl) -2-phenylethyl)indoline-1-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H28 Cl N O5'
_chemical_formula_weight         578.03

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'
Cl Cl 0.1484 0.1585 '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                   14.9648(6)
_cell_length_b                   9.7262(4)
_cell_length_c                   20.3605(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.0019(12)
_cell_angle_gamma                90
_cell_volume                     2927.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorlessprism
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.387
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.225
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38793
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.085
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             5145
_reflns_number_gt                3497
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1547P)²+2.8036P] 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     SHELXL
_refine_ls_extinction_coef       0.056(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5145
_refine_ls_number_parameters     383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.1001
_refine_ls_wR_factor_ref         0.3042
_refine_ls_wR_factor_gt          0.2548
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
Cl1 Cl 0.95099(8) 0.23091(14) 0.99644(6) 0.0909(5) Uani 1 1 d . . . . .
N1 N 0.7174(2) 0.3566(3) 0.80287(16) 0.0732(9) Uani 1 1 d . . . . .
O2 O 0.5834(2) 0.3863(3) 0.73974(16) 0.0893(9) Uani 1 1 d . . . . .
O1 O 0.6915(2) 0.5468(4) 0.73683(17) 0.0974(10) Uani 1 1 d . . . . .
O3 O 0.6192(2) 0.1760(3) 0.81827(14) 0.0830(8) Uani 1 1 d . . . . .
O4 O 0.7852(3) -0.1124(4) 1.13039(19) 0.1169(13) Uani 1 1 d . . . . .
O5 O 0.6272(2) 0.3992(4) 0.92678(16) 0.0983(10) Uani 1 1 d . . . . .
C8 C 0.7583(3) 0.2108(4) 0.89682(18) 0.0679(9) Uani 1 1 d . . . . .
H8 H 0.7832 0.1194 0.8904 0.081 Uiso 1 1 calc R U . . .
C2 C 0.9155(3) 0.3322(4) 0.9279(2) 0.0745(10) Uani 1 1 d . . . . .
C1 C 0.8303(3) 0.3138(4) 0.89081(19) 0.0703(10) Uani 1 1 d . . . . .
C6 C 0.8050(3) 0.3948(4) 0.8341(2) 0.0732(10) Uani 1 1 d . . . . .
C7 C 0.6873(3) 0.2415(4) 0.8365(2) 0.0729(10) Uani 1 1 d . . . . .
C5 C 0.8632(3) 0.4910(5) 0.8137(2) 0.0876(12) Uani 1 1 d . . . . .
H5 H 0.8463 0.5437 0.7757 0.105 Uiso 1 1 calc R U . . .
C3 C 0.9746(3) 0.4295(5) 0.9087(2) 0.0860(12) Uani 1 1 d . . . . .
H3 H 1.0314 0.4427 0.9337 0.103 Uiso 1 1 calc R U . . .
C4 C 0.9479(3) 0.5057(5) 0.8523(3) 0.0918(13) Uani 1 1 d . . . . .
H4 H 0.9880 0.5697 0.8394 0.110 Uiso 1 1 calc R U . . .
C9 C 0.7204(3) 0.2082(4) 0.96227(19) 0.0670(9) Uani 1 1 d . . . . .
H9 H 0.7713 0.1954 0.9983 0.080 Uiso 1 1 calc R U . . .
C10 C 0.6516(3) 0.0866(4) 0.9662(2) 0.0720(10) Uani 1 1 d . . . . .
H10 H 0.6008 0.0967 0.9298 0.086 Uiso 1 1 calc R U . . .
C11 C 0.6161(3) 0.0941(5) 1.0312(2) 0.0786(11) Uani 1 1 d . . . . .
C12 C 0.5418(3) 0.1778(5) 1.0379(3) 0.0934(14) Uani 1 1 d . . . . .
H12 H 0.5107 0.2226 1.0009 0.112 Uiso 1 1 calc R U . . .
C16 C 0.6605(3) 0.0255(5) 1.0869(2) 0.0862(12) Uani 1 1 d . . . . .
C13 C 0.5144(4) 0.1944(7) 1.0995(4) 0.115(2) Uani 1 1 d . . . . .
H13 H 0.4661 0.2520 1.1039 0.138 Uiso 1 1 calc R U . . .
C15 C 0.6315(5) 0.0413(7) 1.1488(3) 0.1134(18) Uani 1 1 d . . . . .
H15 H 0.6610 -0.0044 1.1861 0.136 Uiso 1 1 calc R U . . .
C14 C 0.5585(6) 0.1257(8) 1.1536(4) 0.130(2) Uani 1 1 d . . . . .
H14 H 0.5390 0.1360 1.1945 0.156 Uiso 1 1 calc R U . . .
C18 C 0.7435(3) -0.1165(4) 1.0135(2) 0.0789(11) Uani 1 1 d . . . . .
C23 C 0.6981(3) -0.0492(4) 0.9583(2) 0.0731(10) Uani 1 1 d . . . . .
C22 C 0.7000(3) -0.1053(5) 0.8958(2) 0.0833(12) Uani 1 1 d . . . . .
H22 H 0.6695 -0.0616 0.8583 0.100 Uiso 1 1 calc R U . . .
C17 C 0.7352(3) -0.0698(5) 1.0813(2) 0.0869(12) Uani 1 1 d . . . . .
C21 C 0.7475(4) -0.2270(5) 0.8889(3) 0.0928(14) Uani 1 1 d . . . . .
H21 H 0.7480 -0.2646 0.8470 0.111 Uiso 1 1 calc R U . . .
C19 C 0.7920(3) -0.2372(5) 1.0063(3) 0.0947(14) Uani 1 1 d . . . . .
H19 H 0.8232 -0.2808 1.0436 0.114 Uiso 1 1 calc R U . . .
C20 C 0.7935(4) -0.2909(5) 0.9444(3) 0.1017(16) Uani 1 1 d . . . . .
H20 H 0.8258 -0.3711 0.9398 0.122 Uiso 1 1 calc R U . . .
C24 C 0.6767(3) 0.3466(4) 0.9731(2) 0.0751(10) Uani 1 1 d . . . . .
C30 C 0.6354(4) 0.5233(5) 1.0499(3) 0.0931(14) Uani 1 1 d . . . . .
H30 H 0.5878 0.5471 1.0167 0.112 Uiso 1 1 calc R U . . .
C25 C 0.6931(3) 0.4170(4) 1.0386(2) 0.0769(11) Uani 1 1 d . . . . .
C26 C 0.7628(4) 0.3831(6) 1.0882(2) 0.0998(15) Uani 1 1 d . . . . .
H26 H 0.8016 0.3113 1.0820 0.120 Uiso 1 1 calc R U . . .
C29 C 0.6472(4) 0.5941(6) 1.1093(3) 0.1058(16) Uani 1 1 d . . . . .
H29 H 0.6074 0.6640 1.1164 0.127 Uiso 1 1 calc R U . . .
C28 C 0.7178(4) 0.5606(7) 1.1577(3) 0.1156(19) Uani 1 1 d . . . . .
H28 H 0.7268 0.6090 1.1975 0.139 Uiso 1 1 calc R U . . .
C27 C 0.7755(5) 0.4559(8) 1.1476(3) 0.125(2) Uani 1 1 d . . . . .
H27 H 0.8234 0.4334 1.1808 0.150 Uiso 1 1 calc R U . . .
C31 C 0.6635(3) 0.4403(5) 0.7562(2) 0.0774(11) Uani 1 1 d . . . . .
C32 C 0.5068(3) 0.4641(5) 0.7035(2) 0.0822(12) Uani 1 1 d . . . . .
C33 C 0.4296(4) 0.3620(6) 0.7018(3) 0.1093(17) Uani 1 1 d . . . . .
H33A H 0.4405 0.2840 0.6753 0.164 Uiso 1 1 calc R U . . .
H33B H 0.3738 0.4051 0.6828 0.164 Uiso 1 1 calc R U . . .
H33C H 0.4257 0.3323 0.7462 0.164 Uiso 1 1 calc R U . . .
C34 C 0.4902(5) 0.5890(7) 0.7418(4) 0.139(3) Uani 1 1 d . . . . .
H34A H 0.4928 0.5655 0.7878 0.209 Uiso 1 1 calc R U . . .
H34B H 0.4315 0.6255 0.7249 0.209 Uiso 1 1 calc R U . . .
H34C H 0.5355 0.6567 0.7374 0.209 Uiso 1 1 calc R U . . .
C35 C 0.5239(4) 0.4928(7) 0.6345(3) 0.119(2) Uani 1 1 d . . . . .
H35A H 0.5734 0.5562 0.6361 0.178 Uiso 1 1 calc R U . . .
H35B H 0.4707 0.5321 0.6090 0.178 Uiso 1 1 calc R U . . .
H35C H 0.5387 0.4086 0.6140 0.178 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
Cl1 C2 1.723(4) . ?
N1 C31 1.406(5) . ?
N1 C6 1.414(5) . ?
N1 C7 1.422(5) . ?
O2 C31 1.303(5) . ?
O2 C32 1.472(5) . ?
O1 C31 1.207(5) . ?
O3 C7 1.209(5) . ?
O4 C17 1.223(6) . ?
O5 C24 1.217(5) . ?
C8 C1 1.491(5) . ?
C8 C7 1.523(5) . ?
C8 C9 1.528(5) . ?
C8 H8 0.9800 . ?
C2 C1 1.388(5) . ?
C2 C3 1.392(6) . ?
C1 C6 1.400(6) . ?
C6 C5 1.386(6) . ?
C5 C4 1.389(7) . ?
C5 H5 0.9300 . ?
C3 C4 1.372(7) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C9 C24 1.527(5) . ?
C9 C10 1.578(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.503(6) . ?
C10 C23 1.514(6) . ?
C10 H10 0.9800 . ?
C11 C16 1.392(6) . ?
C11 C12 1.401(6) . ?
C12 C13 1.387(8) . ?
C12 H12 0.9300 . ?
C16 C15 1.404(7) . ?
C16 C17 1.470(7) . ?
C13 C14 1.367(10) . ?
C13 H13 0.9300 . ?
C15 C14 1.382(9) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C18 C23 1.384(6) . ?
C18 C19 1.399(6) . ?
C18 C17 1.476(7) . ?
C23 C22 1.388(6) . ?
C22 C21 1.399(6) . ?
C22 H22 0.9300 . ?
C21 C20 1.376(8) . ?
C21 H21 0.9300 . ?
C19 C20 1.368(8) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C24 C25 1.485(6) . ?
C30 C29 1.379(7) . ?
C30 C25 1.389(6) . ?
C30 H30 0.9300 . ?
C25 C26 1.374(6) . ?
C26 C27 1.388(7) . ?
C26 H26 0.9300 . ?
C29 C28 1.366(8) . ?
C29 H29 0.9300 . ?
C28 C27 1.371(9) . ?
C28 H28 0.9300 . ?
C27 H27 0.9300 . ?
C32 C34 1.485(7) . ?
C32 C35 1.494(7) . ?
C32 C33 1.519(7) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 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
C31 N1 C6 123.0(4) . . ?
C31 N1 C7 126.1(3) . . ?
C6 N1 C7 109.4(3) . . ?
C31 O2 C32 122.3(4) . . ?
C1 C8 C7 102.9(3) . . ?
C1 C8 C9 117.0(3) . . ?
C7 C8 C9 113.6(3) . . ?
C1 C8 H8 107.6 . . ?
C7 C8 H8 107.6 . . ?
C9 C8 H8 107.6 . . ?
C1 C2 C3 120.3(4) . . ?
C1 C2 Cl1 120.5(3) . . ?
C3 C2 Cl1 119.2(3) . . ?
C2 C1 C6 118.9(4) . . ?
C2 C1 C8 131.1(4) . . ?
C6 C1 C8 109.9(3) . . ?
C5 C6 C1 121.7(4) . . ?
C5 C6 N1 128.7(4) . . ?
C1 C6 N1 109.6(3) . . ?
O3 C7 N1 125.6(4) . . ?
O3 C7 C8 126.3(4) . . ?
N1 C7 C8 108.0(3) . . ?
C6 C5 C4 117.4(4) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 122.6(4) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C24 C9 C8 109.7(3) . . ?
C24 C9 C10 110.8(3) . . ?
C8 C9 C10 113.0(3) . . ?
C24 C9 H9 107.7 . . ?
C8 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
C11 C10 C23 111.6(4) . . ?
C11 C10 C9 109.4(3) . . ?
C23 C10 C9 109.5(3) . . ?
C11 C10 H10 108.8 . . ?
C23 C10 H10 108.8 . . ?
C9 C10 H10 108.8 . . ?
C16 C11 C12 119.0(4) . . ?
C16 C11 C10 120.3(4) . . ?
C12 C11 C10 120.6(4) . . ?
C13 C12 C11 120.4(6) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C11 C16 C15 120.1(5) . . ?
C11 C16 C17 120.8(4) . . ?
C15 C16 C17 119.0(5) . . ?
C14 C13 C12 119.8(6) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C14 C15 C16 119.2(6) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C13 C14 C15 121.3(6) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C23 C18 C19 120.5(4) . . ?
C23 C18 C17 120.8(4) . . ?
C19 C18 C17 118.5(4) . . ?
C18 C23 C22 118.7(4) . . ?
C18 C23 C10 120.1(4) . . ?
C22 C23 C10 121.1(4) . . ?
C23 C22 C21 120.6(5) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
O4 C17 C16 121.7(5) . . ?
O4 C17 C18 122.0(5) . . ?
C16 C17 C18 116.3(4) . . ?
C20 C21 C22 119.7(5) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C20 C19 C18 120.1(5) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.4(5) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
O5 C24 C25 119.8(4) . . ?
O5 C24 C9 118.8(4) . . ?
C25 C24 C9 121.4(4) . . ?
C29 C30 C25 121.2(5) . . ?
C29 C30 H30 119.4 . . ?
C25 C30 H30 119.4 . . ?
C26 C25 C30 118.5(4) . . ?
C26 C25 C24 123.4(4) . . ?
C30 C25 C24 118.1(4) . . ?
C25 C26 C27 120.2(5) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C28 C29 C30 119.4(5) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C29 C28 C27 120.2(5) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C27 C26 120.4(6) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
O1 C31 O2 127.9(4) . . ?
O1 C31 N1 121.7(4) . . ?
O2 C31 N1 110.4(4) . . ?
O2 C32 C34 109.8(4) . . ?
O2 C32 C35 109.4(4) . . ?
C34 C32 C35 114.1(5) . . ?
O2 C32 C33 101.8(4) . . ?
C34 C32 C33 111.0(5) . . ?
C35 C32 C33 110.1(4) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C34 H34C O1 0.96 2.57 3.058(8) 111.8 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C34 H34C O1 0.96 2.57 3.058(8) 111.8 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C34 H34C O1 0.96 2.57 3.058(8) 111.8 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C34 H34C O1 0.96 2.57 3.058(8) 111.8 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C34 H34C O1 0.96 2.57 3.058(8) 111.8 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C34 H34C O1 0.96 2.57 3.058(8) 111.8 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C34 H34C O1 0.96 2.57 3.058(8) 111.8 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C34 H34C O1 0.96 2.57 3.058(8) 111.8 .
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C34 H34C O1 0.96 2.57 3.058(8) 111.8 .
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C34 H34C O1 0.96 2.57 3.058(8) 111.8 .
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C34 H34C O1 0.96 2.57 3.058(8) 111.8 .
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565
C5 H5 O1 0.93 2.33 2.844(6) 114.6 .
C5 H5 O3 0.93 2.43 3.278(6) 152.2 2_656
C9 H9 Cl1 0.98 2.72 3.420(4) 129.0 .
C33 H33B O4 0.96 2.55 3.425(7) 151.1 4_565
C35 H35A O1 0.96 2.49 3.045(6) 116.7 .
C35 H35C Cl1 0.96 2.88 3.587(7) 131.0 4_565

_refine_diff_density_max         0.518
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.091

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate/n-hexane'
