# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_OSJ27M
_database_code_depnum_ccdc_archive 'CCDC 1409974'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
"(?)-(3aR,9aR)-rel-3a,4,9,9a-tetrahydro-4-[(1R)-1-N-benzylaminoethyl]-2-methyl-,4,9[1',2']-benzeno-1H-benz[f]isoindole-1,3(2H)-dione "
_chemical_name_common            ?
_chemical_melting_point          473
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H26 N2 O2'
_chemical_formula_weight         422.51

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                   10.2636(18)
_cell_length_b                   10.7862(18)
_cell_length_c                   11.475(2)
_cell_angle_alpha                96.250(3)
_cell_angle_beta                 98.454(3)
_cell_angle_gamma                104.549(3)
_cell_volume                     1202.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5552
_cell_measurement_theta_min      4.901
_cell_measurement_theta_max      54.950

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_T_max  0.9768
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART1000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 100
_diffrn_reflns_number            11663
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.815
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             4236
_reflns_number_gt                3388
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0954P)²+0.4985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4236
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1655
_refine_ls_wR_factor_gt          0.1572
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
N1 N -0.28170(18) 0.45300(17) 0.69727(16) 0.0336(4) Uani 1 1 d . . . . .
N2 N 0.19105(17) 0.44199(16) 0.80958(15) 0.0273(4) Uani 1 1 d . . . . .
H2A H 0.1590 0.4217 0.8741 0.033 Uiso 1 1 calc R U . . .
O1 O -0.12283(16) 0.35361(14) 0.64225(13) 0.0370(4) Uani 1 1 d . . . . .
O2 O -0.39766(15) 0.57722(16) 0.79218(15) 0.0438(4) Uani 1 1 d . . . . .
C1 C 0.0341(2) 0.7160(2) 0.60947(18) 0.0303(5) Uani 1 1 d . . . . .
H1A H 0.0890 0.6700 0.5731 0.036 Uiso 1 1 calc R U . . .
C2 C -0.0230(2) 0.7997(2) 0.5484(2) 0.0366(5) Uani 1 1 d . . . . .
H2B H -0.0049 0.8125 0.4711 0.044 Uiso 1 1 calc R U . . .
C2A C 0.1622(2) 0.54611(19) 0.74578(17) 0.0263(4) Uani 1 1 d . . . . .
H2AA H 0.1142 0.5054 0.6630 0.032 Uiso 1 1 calc R U . . .
C3 C -0.1061(2) 0.8648(2) 0.5995(2) 0.0394(5) Uani 1 1 d . . . . .
H3A H -0.1444 0.9222 0.5574 0.047 Uiso 1 1 calc R U . . .
C4 C -0.1334(2) 0.8461(2) 0.7117(2) 0.0343(5) Uani 1 1 d . . . . .
H4A H -0.1920 0.8890 0.7461 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0737(2) 0.82962(19) 1.08726(18) 0.0305(5) Uani 1 1 d . . . . .
H5A H 0.0131 0.8732 1.1173 0.037 Uiso 1 1 calc R U . . .
C6 C 0.2002(2) 0.8391(2) 1.15605(18) 0.0317(5) Uani 1 1 d . . . . .
H6A H 0.2266 0.8897 1.2330 0.038 Uiso 1 1 calc R U . . .
C7 C 0.2873(2) 0.77440(19) 1.11185(19) 0.0307(5) Uani 1 1 d . . . . .
H7A H 0.3737 0.7810 1.1590 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2502(2) 0.69982(19) 0.99930(17) 0.0266(4) Uani 1 1 d . . . . .
H8A H 0.3104 0.6546 0.9707 0.032 Uiso 1 1 calc R U . . .
C9 C 0.06516(19) 0.61138(18) 0.80410(17) 0.0245(4) Uani 1 1 d . . . . .
C10 C -0.0993(2) 0.73259(18) 0.89477(17) 0.0264(4) Uani 1 1 d . . . . .
H10A H -0.1591 0.7818 0.9288 0.032 Uiso 1 1 calc R U . . .
C11 C 0.0106(2) 0.69965(18) 0.72389(18) 0.0259(4) Uani 1 1 d . . . . .
C12 C -0.0748(2) 0.76469(19) 0.77364(18) 0.0275(4) Uani 1 1 d . . . . .
C14 C 0.1255(2) 0.69143(18) 0.92885(17) 0.0244(4) Uani 1 1 d . . . . .
C15 C 0.0366(2) 0.75667(18) 0.97510(17) 0.0255(4) Uani 1 1 d . . . . .
C16 C -0.1634(2) 0.58315(18) 0.87806(18) 0.0262(4) Uani 1 1 d . . . . .
H16A H -0.1800 0.5556 0.9562 0.031 Uiso 1 1 calc R U . . .
C17 C -0.06808(19) 0.51130(18) 0.82518(17) 0.0248(4) Uani 1 1 d . . . . .
H17A H -0.0413 0.4535 0.8813 0.030 Uiso 1 1 calc R U . . .
C18 C -0.2951(2) 0.5418(2) 0.78843(19) 0.0316(5) Uani 1 1 d . . . . .
C19 C -0.1545(2) 0.42938(19) 0.71140(18) 0.0283(5) Uani 1 1 d . . . . .
C20 C 0.2798(2) 0.3758(2) 0.75289(19) 0.0309(5) Uani 1 1 d . . . . .
H20A H 0.3710 0.4372 0.7588 0.037 Uiso 1 1 calc R U . . .
H20B H 0.2400 0.3466 0.6673 0.037 Uiso 1 1 calc R U . . .
C21 C 0.2954(2) 0.26044(19) 0.81175(18) 0.0277(4) Uani 1 1 d . . . . .
C22 C 0.3699(2) 0.2776(2) 0.9259(2) 0.0331(5) Uani 1 1 d . . . . .
H22A H 0.4129 0.3628 0.9669 0.040 Uiso 1 1 calc R U . . .
C23 C 0.3826(2) 0.1720(2) 0.9811(2) 0.0372(5) Uani 1 1 d . . . . .
H23A H 0.4331 0.1854 1.0599 0.045 Uiso 1 1 calc R U . . .
C24 C 0.3222(2) 0.0476(2) 0.9222(2) 0.0403(6) Uani 1 1 d . . . . .
H24A H 0.3318 -0.0248 0.9596 0.048 Uiso 1 1 calc R U . . .
C25 C 0.2482(3) 0.0296(2) 0.8093(2) 0.0484(6) Uani 1 1 d . . . . .
H25A H 0.2059 -0.0558 0.7683 0.058 Uiso 1 1 calc R U . . .
C26 C 0.2345(2) 0.1353(2) 0.7541(2) 0.0384(5) Uani 1 1 d . . . . .
H26A H 0.1827 0.1214 0.6759 0.046 Uiso 1 1 calc R U . . .
C27 C 0.2961(2) 0.6441(2) 0.7356(2) 0.0313(5) Uani 1 1 d . . . . .
H27A H 0.2749 0.7125 0.6930 0.047 Uiso 1 1 calc R U . . .
H27B H 0.3481 0.6824 0.8156 0.047 Uiso 1 1 calc R U . . .
H27C H 0.3507 0.5997 0.6918 0.047 Uiso 1 1 calc R U . . .
C28 C -0.3926(3) 0.3886(3) 0.5987(2) 0.0532(7) Uani 1 1 d . . . . .
H28A H -0.4727 0.4204 0.6069 0.080 Uiso 1 1 calc R U . . .
H28B H -0.3636 0.4072 0.5233 0.080 Uiso 1 1 calc R U . . .
H28C H -0.4161 0.2949 0.5994 0.080 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
N1 C19 1.382(3) . ?
N1 C18 1.386(3) . ?
N1 C28 1.452(3) . ?
N2 C20 1.470(2) . ?
N2 C2A 1.472(2) . ?
N2 H2A 0.8800 . ?
O1 C19 1.213(2) . ?
O2 C18 1.211(2) . ?
C1 C2 1.390(3) . ?
C1 C11 1.391(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.386(3) . ?
C2 H2B 0.9500 . ?
C2A C27 1.537(3) . ?
C2A C9 1.543(3) . ?
C2A H2AA 1.0000 . ?
C3 C4 1.382(3) . ?
C3 H3A 0.9500 . ?
C4 C12 1.384(3) . ?
C4 H4A 0.9500 . ?
C5 C15 1.380(3) . ?
C5 C6 1.390(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.383(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.391(3) . ?
C7 H7A 0.9500 . ?
C8 C14 1.387(3) . ?
C8 H8A 0.9500 . ?
C9 C14 1.543(3) . ?
C9 C11 1.541(3) . ?
C9 C17 1.583(3) . ?
C10 C15 1.501(3) . ?
C10 C12 1.510(3) . ?
C10 C16 1.559(3) . ?
C10 H10A 1.0000 . ?
C11 C12 1.399(3) . ?
C14 C15 1.411(3) . ?
C16 C18 1.507(3) . ?
C16 C17 1.543(3) . ?
C16 H16A 1.0000 . ?
C17 C19 1.512(3) . ?
C17 H17A 1.0000 . ?
C20 C21 1.510(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C26 1.382(3) . ?
C21 C22 1.384(3) . ?
C22 C23 1.386(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.380(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.370(4) . ?
C24 H24A 0.9500 . ?
C25 C26 1.390(3) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 N1 C18 113.46(18) . . ?
C19 N1 C28 123.64(19) . . ?
C18 N1 C28 122.87(19) . . ?
C20 N2 C2A 112.06(15) . . ?
C20 N2 H2A 124.0 . . ?
C2A N2 H2A 124.0 . . ?
C2 C1 C11 119.91(19) . . ?
C2 C1 H1A 120.0 . . ?
C11 C1 H1A 120.0 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2B 119.8 . . ?
C1 C2 H2B 119.8 . . ?
N2 C2A C27 110.63(16) . . ?
N2 C2A C9 111.31(15) . . ?
C27 C2A C9 112.34(16) . . ?
N2 C2A H2AA 107.4 . . ?
C27 C2A H2AA 107.4 . . ?
C9 C2A H2AA 107.4 . . ?
C2 C3 C4 120.02(19) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C12 C4 C3 119.68(19) . . ?
C12 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C15 C5 C6 119.74(18) . . ?
C15 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C7 C6 C5 119.69(19) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C6 C7 C8 120.91(19) . . ?
C6 C7 H7A 119.5 . . ?
C8 C7 H7A 119.5 . . ?
C14 C8 C7 120.02(18) . . ?
C14 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C14 C9 C11 107.86(15) . . ?
C14 C9 C2A 115.69(16) . . ?
C11 C9 C2A 111.48(15) . . ?
C14 C9 C17 103.17(15) . . ?
C11 C9 C17 104.44(15) . . ?
C2A C9 C17 113.28(15) . . ?
C15 C10 C12 108.58(16) . . ?
C15 C10 C16 105.10(15) . . ?
C12 C10 C16 106.34(16) . . ?
C15 C10 H10A 112.1 . . ?
C12 C10 H10A 112.1 . . ?
C16 C10 H10A 112.1 . . ?
C1 C11 C12 118.89(17) . . ?
C1 C11 C9 126.93(17) . . ?
C12 C11 C9 114.13(16) . . ?
C4 C12 C11 120.96(19) . . ?
C4 C12 C10 125.10(18) . . ?
C11 C12 C10 113.90(16) . . ?
C8 C14 C15 118.68(18) . . ?
C8 C14 C9 127.53(17) . . ?
C15 C14 C9 113.71(16) . . ?
C5 C15 C14 120.95(18) . . ?
C5 C15 C10 125.06(17) . . ?
C14 C15 C10 113.92(17) . . ?
C18 C16 C17 104.83(16) . . ?
C18 C16 C10 111.39(15) . . ?
C17 C16 C10 110.35(15) . . ?
C18 C16 H16A 110.1 . . ?
C17 C16 H16A 110.1 . . ?
C10 C16 H16A 110.1 . . ?
C19 C17 C16 104.75(15) . . ?
C19 C17 C9 113.26(15) . . ?
C16 C17 C9 110.54(15) . . ?
C19 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
C9 C17 H17A 109.4 . . ?
O2 C18 N1 123.9(2) . . ?
O2 C18 C16 127.59(19) . . ?
N1 C18 C16 108.48(17) . . ?
O1 C19 N1 123.7(2) . . ?
O1 C19 C17 127.91(19) . . ?
N1 C19 C17 108.41(16) . . ?
N2 C20 C21 111.05(16) . . ?
N2 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
N2 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C26 C21 C22 118.20(19) . . ?
C26 C21 C20 121.14(19) . . ?
C22 C21 C20 120.65(18) . . ?
C21 C22 C23 120.9(2) . . ?
C21 C22 H22A 119.6 . . ?
C23 C22 H22A 119.6 . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23A 119.8 . . ?
C22 C23 H23A 119.8 . . ?
C25 C24 C23 119.3(2) . . ?
C25 C24 H24A 120.4 . . ?
C23 C24 H24A 120.4 . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 H25A 119.8 . . ?
C26 C25 H25A 119.8 . . ?
C21 C26 C25 120.8(2) . . ?
C21 C26 H26A 119.6 . . ?
C25 C26 H26A 119.6 . . ?
C2A C27 H27A 109.5 . . ?
C2A C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C2A C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N1 C28 H28A 109.5 . . ?
N1 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N1 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_refine_diff_density_max         0.678
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Petroleum ether / dichloromethane'
####################################################################### 
# 
# 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_osj51redo_a
_database_code_depnum_ccdc_archive 'CCDC 1409975'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'(?)-(3aS,9aS)-3a,4,9,9a-Tetrahydro-4-[(1R)-ethyl-trifluoroacetamido]-2-methyl-4,9-[1?,2?]benzeno-1H-benzo[f]isoindole-1,3-(2H)-dione '
_chemical_name_common            ?
_chemical_melting_point          523
_chemical_formula_moiety         'C23 H18 F3 N2 O3'
_chemical_formula_sum            'C23 H18 F3 N2 O3'
_chemical_formula_weight         427.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   15.275(3)
_cell_length_b                   14.422(2)
_cell_length_c                   17.487(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3852.6(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2794
_cell_measurement_theta_min      4.528
_cell_measurement_theta_max      43.793

_exptl_crystal_description       Needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             1768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker smart4000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 100
_diffrn_reflns_number            79754
_diffrn_reflns_av_unetI/netI     0.1782
_diffrn_reflns_av_R_equivalents  0.3594
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.265
_diffrn_reflns_theta_max         30.924
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5993
_reflns_number_gt                2592
_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       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0718P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5993
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1500
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1705
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_restrained_S_all      0.810
_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
O1 O 0.93099(10) 0.20858(11) 0.23823(10) 0.0312(4) Uani 1 1 d . . . . .
O2 O 0.80070(10) 0.14129(11) 0.46541(10) 0.0316(4) Uani 1 1 d . . . . .
O3 O 0.58110(11) 0.31635(12) 0.57539(11) 0.0407(5) Uani 1 1 d . . . . .
N1 N 0.85449(12) 0.16042(13) 0.34393(12) 0.0270(5) Uani 1 1 d . . . . .
N2 N 0.68844(12) 0.41489(13) 0.53288(11) 0.0273(5) Uani 1 1 d . . . . .
C1 C 0.89945(14) 0.47025(15) 0.37436(14) 0.0248(5) Uani 1 1 d . . . . .
C6 C 0.85589(15) 0.45324(15) 0.44321(14) 0.0246(5) Uani 1 1 d . . . . .
C18 C 0.83915(14) 0.18843(16) 0.41843(15) 0.0259(5) Uani 1 1 d . . . . .
C5 C 0.86302(15) 0.51784(16) 0.50185(14) 0.0272(5) Uani 1 1 d . . . . .
H5 H 0.8357 0.5063 0.5497 0.033 Uiso 1 1 calc R U . . .
C17 C 0.90738(14) 0.22132(16) 0.30367(15) 0.0265(5) Uani 1 1 d . . . . .
C2 C 0.94744(15) 0.55125(16) 0.36333(14) 0.0262(5) Uani 1 1 d . . . . .
H2 H 0.9770 0.5618 0.3163 0.031 Uiso 1 1 calc R U . . .
C16 C 0.87790(14) 0.28398(15) 0.42976(14) 0.0237(5) Uani 1 1 d . . . . .
H16 H 0.9205 0.2832 0.4732 0.028 Uiso 1 1 calc R U . . .
C9 C 0.74776(14) 0.35685(15) 0.37199(14) 0.0234(5) Uani 1 1 d . . . . .
C15 C 0.92642(14) 0.30391(15) 0.35368(14) 0.0242(5) Uani 1 1 d . . . . .
H15 H 0.9908 0.3099 0.3628 0.029 Uiso 1 1 calc R U . . .
C13 C 0.75243(15) 0.36850(16) 0.23359(14) 0.0273(6) Uani 1 1 d . . . . .
H13 H 0.7839 0.3813 0.1879 0.033 Uiso 1 1 calc R U . . .
C14 C 0.79359(14) 0.37530(15) 0.30407(14) 0.0241(5) Uani 1 1 d . . . . .
C10 C 0.66052(14) 0.33040(16) 0.36784(15) 0.0280(6) Uani 1 1 d . . . . .
H10 H 0.6290 0.3169 0.4133 0.034 Uiso 1 1 calc R U . . .
C8 C 0.88979(14) 0.39329(15) 0.31608(14) 0.0237(5) Uani 1 1 d . . . . .
H8 H 0.9204 0.4082 0.2671 0.028 Uiso 1 1 calc R U . . .
C7 C 0.80496(14) 0.36038(15) 0.44420(14) 0.0249(5) Uani 1 1 d . . . . .
C22 C 0.61122(16) 0.39361(17) 0.56482(14) 0.0285(6) Uani 1 1 d . . . . .
C3 C 0.95179(15) 0.61644(16) 0.42154(15) 0.0290(6) Uani 1 1 d . . . . .
H3 H 0.9833 0.6725 0.4140 0.035 Uiso 1 1 calc R U . . .
C4 C 0.91027(14) 0.59994(16) 0.49062(15) 0.0283(6) Uani 1 1 d . . . . .
H4 H 0.9139 0.6445 0.5305 0.034 Uiso 1 1 calc R U . . .
C21 C 0.75205(15) 0.33894(16) 0.51724(14) 0.0259(5) Uani 1 1 d . . . . .
H21 H 0.7168 0.2821 0.5063 0.031 Uiso 1 1 calc R U . . .
C23 C 0.55870(15) 0.47560(18) 0.59678(15) 0.0299(6) Uani 1 1 d . . . . .
C19 C 0.81684(16) 0.07644(16) 0.31075(16) 0.0341(6) Uani 1 1 d . . . . .
H19A H 0.8476 0.0220 0.3308 0.051 Uiso 1 1 calc R U . . .
H19B H 0.8230 0.0784 0.2550 0.051 Uiso 1 1 calc R U . . .
H19C H 0.7547 0.0726 0.3242 0.051 Uiso 1 1 calc R U . . .
C11 C 0.61924(16) 0.32364(16) 0.29734(15) 0.0312(6) Uani 1 1 d . . . . .
H11 H 0.5594 0.3058 0.2948 0.037 Uiso 1 1 calc R U . . .
C12 C 0.66482(15) 0.34274(17) 0.23034(15) 0.0312(6) Uani 1 1 d . . . . .
H12 H 0.6361 0.3382 0.1823 0.037 Uiso 1 1 calc R U . . .
C20 C 0.80606(16) 0.31821(18) 0.58911(15) 0.0328(6) Uani 1 1 d . . . . .
H20A H 0.8471 0.3692 0.5983 0.049 Uiso 1 1 calc R U . . .
H20B H 0.8388 0.2604 0.5818 0.049 Uiso 1 1 calc R U . . .
H20C H 0.7668 0.3118 0.6331 0.049 Uiso 1 1 calc R U . . .
F1 F 0.59196(9) 0.55945(9) 0.58008(8) 0.0367(4) Uani 1 1 d . . . . .
F3 F 0.47600(9) 0.47419(10) 0.57237(8) 0.0392(4) Uani 1 1 d . . . . .
F2 F 0.55593(10) 0.46844(10) 0.67315(8) 0.0432(4) 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
O1 C17 1.214(3) . ?
O2 C18 1.218(3) . ?
O3 C22 1.220(3) . ?
N1 C18 1.384(3) . ?
N1 C17 1.386(3) . ?
N1 C19 1.461(3) . ?
N2 C22 1.341(3) . ?
N2 C21 1.490(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.397(3) . ?
C1 C8 1.514(3) . ?
C6 C5 1.390(3) . ?
C6 C7 1.549(3) . ?
C18 C16 1.513(3) . ?
C5 C4 1.400(3) . ?
C5 H5 0.9500 . ?
C17 C15 1.506(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C16 C15 1.550(3) . ?
C16 C7 1.587(3) . ?
C16 H16 1.0000 . ?
C9 C10 1.388(3) . ?
C9 C14 1.404(3) . ?
C9 C7 1.537(3) . ?
C15 C8 1.552(3) . ?
C15 H15 1.0000 . ?
C13 C14 1.387(3) . ?
C13 C12 1.390(3) . ?
C13 H13 0.9500 . ?
C14 C8 1.507(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C8 H8 1.0000 . ?
C7 C21 1.543(3) . ?
C22 C23 1.534(3) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C21 C20 1.533(3) . ?
C21 H21 1.0000 . ?
C23 F3 1.334(3) . ?
C23 F2 1.340(3) . ?
C23 F1 1.344(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C11 C12 1.390(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C18 N1 C17 113.1(2) . . ?
C18 N1 C19 123.3(2) . . ?
C17 N1 C19 123.6(2) . . ?
C22 N2 C21 118.82(19) . . ?
C2 C1 C6 121.2(2) . . ?
C2 C1 C8 125.0(2) . . ?
C6 C1 C8 113.9(2) . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 127.6(2) . . ?
C1 C6 C7 113.6(2) . . ?
O2 C18 N1 123.6(2) . . ?
O2 C18 C16 127.5(2) . . ?
N1 C18 C16 108.8(2) . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
O1 C17 N1 123.8(2) . . ?
O1 C17 C15 127.6(2) . . ?
N1 C17 C15 108.6(2) . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C18 C16 C15 104.10(19) . . ?
C18 C16 C7 112.25(18) . . ?
C15 C16 C7 110.09(18) . . ?
C18 C16 H16 110.1 . . ?
C15 C16 H16 110.1 . . ?
C7 C16 H16 110.1 . . ?
C10 C9 C14 119.1(2) . . ?
C10 C9 C7 126.7(2) . . ?
C14 C9 C7 113.92(19) . . ?
C17 C15 C16 105.04(18) . . ?
C17 C15 C8 109.95(19) . . ?
C16 C15 C8 110.21(18) . . ?
C17 C15 H15 110.5 . . ?
C16 C15 H15 110.5 . . ?
C8 C15 H15 110.5 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 C8 125.3(2) . . ?
C9 C14 C8 113.6(2) . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C14 C8 C1 108.37(18) . . ?
C14 C8 C15 105.52(18) . . ?
C1 C8 C15 106.77(19) . . ?
C14 C8 H8 111.9 . . ?
C1 C8 H8 111.9 . . ?
C15 C8 H8 111.9 . . ?
C9 C7 C21 112.08(19) . . ?
C9 C7 C6 107.76(18) . . ?
C21 C7 C6 116.46(19) . . ?
C9 C7 C16 104.21(18) . . ?
C21 C7 C16 111.12(18) . . ?
C6 C7 C16 104.24(17) . . ?
O3 C22 N2 127.2(2) . . ?
O3 C22 C23 116.8(2) . . ?
N2 C22 C23 115.8(2) . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N2 C21 C20 110.12(19) . . ?
N2 C21 C7 110.26(18) . . ?
C20 C21 C7 115.85(19) . . ?
N2 C21 H21 106.7 . . ?
C20 C21 H21 106.7 . . ?
C7 C21 H21 106.7 . . ?
F3 C23 F2 106.73(19) . . ?
F3 C23 F1 107.6(2) . . ?
F2 C23 F1 107.33(19) . . ?
F3 C23 C22 111.5(2) . . ?
F2 C23 C22 108.7(2) . . ?
F1 C23 C22 114.6(2) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.703
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.091

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane / 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_osj53
_database_code_depnum_ccdc_archive 'CCDC 1409976'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'(?)-(3aS,9aS)-3a,4,9,9a-Tetrahydro-4-[(1R)-ethyl-tert-butylcarbamato]-2-methyl-4,9-[1?,2?]benzeno-1H-benzo[f]isoindole-1,3-(2H)-dione '
_chemical_name_common            ?
_chemical_melting_point          508
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H28 N2 O4'
_chemical_formula_weight         432.50

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'
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_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.9540(12)
_cell_length_b                   9.4917(8)
_cell_length_c                   16.5072(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.913(5)
_cell_angle_gamma                90
_cell_volume                     2229.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2324
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      23.59

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 100
_diffrn_reflns_number            24715
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.507
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3916
_reflns_number_gt                2225
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0729P)²+0.2665P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3916
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1555
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
N1 N 0.70901(18) 0.7518(3) 1.15814(15) 0.0224(6) Uani 1 1 d . . . . .
N2 N 0.74805(17) 0.3935(3) 0.89805(16) 0.0253(6) Uani 1 1 d . . . . .
H2 H 0.7042 0.4080 0.8492 0.030 Uiso 1 1 calc R U . . .
O1 O 0.78049(14) 0.5368(2) 1.16240(13) 0.0244(5) Uani 1 1 d . . . . .
O2 O 0.60931(16) 0.9424(2) 1.12455(14) 0.0379(6) Uani 1 1 d . . . . .
O3 O 0.89594(15) 0.3124(2) 0.96196(14) 0.0301(6) Uani 1 1 d . . . . .
O4 O 0.83353(14) 0.3294(2) 0.81663(13) 0.0251(5) Uani 1 1 d . . . . .
C1 C 0.5258(2) 0.6883(3) 0.88266(18) 0.0195(7) Uani 1 1 d . . . . .
C2 C 0.4388(2) 0.7050(3) 0.82195(19) 0.0244(8) Uani 1 1 d . . . . .
H2A H 0.4061 0.7920 0.8172 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3996(2) 0.5936(3) 0.76809(19) 0.0238(8) Uani 1 1 d . . . . .
H3 H 0.3400 0.6039 0.7264 0.029 Uiso 1 1 calc R U . . .
C4 C 0.4483(2) 0.4670(3) 0.77555(19) 0.0225(7) Uani 1 1 d . . . . .
H4 H 0.4221 0.3915 0.7380 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5350(2) 0.4497(3) 0.83740(18) 0.0217(7) Uani 1 1 d . . . . .
H5 H 0.5671 0.3621 0.8424 0.026 Uiso 1 1 calc R U . . .
C6 C 0.5750(2) 0.5603(3) 0.89191(19) 0.0200(7) Uani 1 1 d . . . . .
C7 C 0.6679(2) 0.5597(3) 0.96604(18) 0.0192(7) Uani 1 1 d . . . . .
C8 C 0.5733(2) 0.7995(3) 0.94684(18) 0.0210(7) Uani 1 1 d . . . . .
H8 H 0.5381 0.8907 0.9372 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6734(2) 0.8159(3) 0.94517(18) 0.0205(7) Uani 1 1 d . . . . .
C10 C 0.7162(2) 0.9436(3) 0.93822(19) 0.0285(8) Uani 1 1 d . . . . .
H10 H 0.6810 1.0286 0.9308 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8101(2) 0.9467(4) 0.9422(2) 0.0313(8) Uani 1 1 d . . . . .
H11 H 0.8394 1.0337 0.9373 0.038 Uiso 1 1 calc R U . . .
C12 C 0.8610(2) 0.8224(3) 0.95329(19) 0.0291(8) Uani 1 1 d . . . . .
H12 H 0.9254 0.8248 0.9564 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8188(2) 0.6938(3) 0.96001(18) 0.0232(7) Uani 1 1 d . . . . .
H13 H 0.8542 0.6091 0.9676 0.028 Uiso 1 1 calc R U . . .
C14 C 0.7246(2) 0.6907(3) 0.95557(17) 0.0185(7) Uani 1 1 d . . . . .
C15 C 0.6365(2) 0.5939(3) 1.04704(18) 0.0183(7) Uani 1 1 d . . . . .
H15 H 0.5966 0.5151 1.0567 0.022 Uiso 1 1 calc R U . . .
C16 C 0.5798(2) 0.7321(3) 1.03442(18) 0.0210(7) Uani 1 1 d . . . . .
H16 H 0.5151 0.7122 1.0370 0.025 Uiso 1 1 calc R U . . .
C17 C 0.7174(2) 0.6178(3) 1.12729(19) 0.0195(7) Uani 1 1 d . . . . .
C18 C 0.6312(2) 0.8242(3) 1.10858(19) 0.0256(8) Uani 1 1 d . . . . .
C19 C 0.7731(2) 0.8059(3) 1.2376(2) 0.0328(8) Uani 1 1 d . . . . .
H19A H 0.7473 0.7866 1.2843 0.049 Uiso 1 1 calc R U . . .
H19B H 0.7806 0.9078 1.2327 0.049 Uiso 1 1 calc R U . . .
H19C H 0.8343 0.7598 1.2491 0.049 Uiso 1 1 calc R U . . .
C20 C 0.6907(2) 0.2950(3) 1.0116(2) 0.0269(8) Uani 1 1 d . . . . .
H20A H 0.7372 0.2191 1.0211 0.040 Uiso 1 1 calc R U . . .
H20B H 0.6318 0.2642 0.9700 0.040 Uiso 1 1 calc R U . . .
H20C H 0.6793 0.3182 1.0655 0.040 Uiso 1 1 calc R U . . .
C21 C 0.7277(2) 0.4250(3) 0.97779(19) 0.0217(7) Uani 1 1 d . . . . .
H21 H 0.7894 0.4483 1.0207 0.026 Uiso 1 1 calc R U . . .
C22 C 0.8327(2) 0.3426(3) 0.8979(2) 0.0243(8) Uani 1 1 d . . . . .
C24 C 0.9236(2) 0.3037(3) 0.7989(2) 0.0269(8) Uani 1 1 d . . . . .
C25 C 0.9915(2) 0.4208(4) 0.8387(2) 0.0353(9) Uani 1 1 d . . . . .
H25A H 1.0076 0.4155 0.9009 0.053 Uiso 1 1 calc R U . . .
H25B H 0.9622 0.5120 0.8190 0.053 Uiso 1 1 calc R U . . .
H25C H 1.0487 0.4107 0.8221 0.053 Uiso 1 1 calc R U . . .
C26 C 0.9606(2) 0.1576(3) 0.8307(2) 0.0342(9) Uani 1 1 d . . . . .
H26A H 0.9115 0.0873 0.8069 0.051 Uiso 1 1 calc R U . . .
H26B H 0.9782 0.1554 0.8930 0.051 Uiso 1 1 calc R U . . .
H26C H 1.0157 0.1363 0.8127 0.051 Uiso 1 1 calc R U . . .
C27 C 0.8943(2) 0.3088(4) 0.7024(2) 0.0326(8) Uani 1 1 d . . . . .
H27A H 0.8679 0.4017 0.6828 0.049 Uiso 1 1 calc R U . . .
H27B H 0.8468 0.2362 0.6789 0.049 Uiso 1 1 calc R U . . .
H27C H 0.9492 0.2917 0.6833 0.049 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
N1 C18 1.382(4) . ?
N1 C17 1.390(4) . ?
N1 C19 1.459(4) . ?
N2 C22 1.356(4) . ?
N2 C21 1.470(3) . ?
N2 H2 0.8800 . ?
O1 C17 1.217(3) . ?
O2 C18 1.220(4) . ?
O3 C22 1.217(4) . ?
O4 C22 1.351(4) . ?
O4 C24 1.484(3) . ?
C1 C2 1.386(4) . ?
C1 C6 1.405(4) . ?
C1 C8 1.509(4) . ?
C2 C3 1.389(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.543(4) . ?
C7 C21 1.538(4) . ?
C7 C14 1.544(4) . ?
C7 C15 1.581(4) . ?
C8 C9 1.514(4) . ?
C8 C16 1.556(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.392(4) . ?
C9 C14 1.395(4) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(4) . ?
C13 H13 0.9500 . ?
C15 C17 1.512(4) . ?
C15 C16 1.540(4) . ?
C15 H15 1.0000 . ?
C16 C18 1.509(4) . ?
C16 H16 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.527(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 1.0000 . ?
C24 C25 1.513(4) . ?
C24 C27 1.517(4) . ?
C24 C26 1.525(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
C18 N1 C17 113.1(3) . . ?
C18 N1 C19 123.9(3) . . ?
C17 N1 C19 122.9(3) . . ?
C22 N2 C21 121.7(3) . . ?
C22 N2 H2 119.2 . . ?
C21 N2 H2 119.2 . . ?
C22 O4 C24 119.8(2) . . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 C8 124.2(3) . . ?
C6 C1 C8 114.3(3) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 C7 127.8(3) . . ?
C1 C6 C7 113.8(3) . . ?
C21 C7 C6 116.7(2) . . ?
C21 C7 C14 111.4(2) . . ?
C6 C7 C14 107.5(2) . . ?
C21 C7 C15 112.1(2) . . ?
C6 C7 C15 103.9(2) . . ?
C14 C7 C15 104.2(2) . . ?
C1 C8 C9 108.3(2) . . ?
C1 C8 C16 104.3(2) . . ?
C9 C8 C16 106.2(2) . . ?
C1 C8 H8 112.5 . . ?
C9 C8 H8 112.5 . . ?
C16 C8 H8 112.5 . . ?
C10 C9 C14 120.2(3) . . ?
C10 C9 C8 125.0(3) . . ?
C14 C9 C8 114.7(3) . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.7(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.4(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C9 119.9(3) . . ?
C13 C14 C7 126.5(3) . . ?
C9 C14 C7 113.6(2) . . ?
C17 C15 C16 104.5(2) . . ?
C17 C15 C7 113.9(2) . . ?
C16 C15 C7 110.8(2) . . ?
C17 C15 H15 109.2 . . ?
C16 C15 H15 109.2 . . ?
C7 C15 H15 109.2 . . ?
C18 C16 C15 105.2(2) . . ?
C18 C16 C8 112.7(3) . . ?
C15 C16 C8 110.5(2) . . ?
C18 C16 H16 109.4 . . ?
C15 C16 H16 109.4 . . ?
C8 C16 H16 109.4 . . ?
O1 C17 N1 123.2(3) . . ?
O1 C17 C15 128.1(3) . . ?
N1 C17 C15 108.7(3) . . ?
O2 C18 N1 124.3(3) . . ?
O2 C18 C16 127.2(3) . . ?
N1 C18 C16 108.5(3) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C20 111.2(2) . . ?
N2 C21 C7 109.2(2) . . ?
C20 C21 C7 117.1(2) . . ?
N2 C21 H21 106.2 . . ?
C20 C21 H21 106.2 . . ?
C7 C21 H21 106.2 . . ?
O3 C22 O4 126.8(3) . . ?
O3 C22 N2 124.0(3) . . ?
O4 C22 N2 109.2(3) . . ?
O4 C24 C25 108.8(2) . . ?
O4 C24 C27 102.4(2) . . ?
C25 C24 C27 111.8(3) . . ?
O4 C24 C26 109.7(2) . . ?
C25 C24 C26 113.2(3) . . ?
C27 C24 C26 110.3(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.063

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane / 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_osj19
_database_code_depnum_ccdc_archive 'CCDC 1409977'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(?)-(3aS,9aS)-3a,4,9,9a-Tetrahydro-4-[(1R)-ethylacetamido]-2-methyl-4,9-[1?,2?]benzeno-1H-benzo[f]isoindole-1,3-(2H)-dione '
_chemical_name_common            ?
_chemical_melting_point          573
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 N2 O3'
_chemical_formula_weight         374.43

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   17.583(2)
_cell_length_b                   11.5915(14)
_cell_length_c                   17.893(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3646.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3981
_cell_measurement_theta_min      4.553
_cell_measurement_theta_max      51.357

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9636
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART1000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 100
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            32857
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3215
_reflns_number_gt                2136
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0549P)²+4.0964P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3215
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.11348(13) 0.58172(19) 0.12810(12) 0.0274(5) Uani 1 1 d . . .
N2 N 0.12694(13) 0.3102(2) 0.38751(12) 0.0290(6) Uani 1 1 d . . .
H2 H 0.0842 0.2720 0.3942 0.035 Uiso 1 1 calc R . .
O1 O 0.19911(11) 0.56598(17) 0.22398(11) 0.0358(5) Uani 1 1 d . . .
O2 O 0.00506(12) 0.61366(19) 0.05974(12) 0.0438(6) Uani 1 1 d . . .
O3 O 0.25389(12) 0.3168(2) 0.40567(14) 0.0549(7) Uani 1 1 d . . .
C1 C 0.13536(14) 0.2603(2) 0.21785(15) 0.0250(6) Uani 1 1 d . . .
H1 H 0.1741 0.2579 0.2548 0.030 Uiso 1 1 calc R . .
C2 C 0.13861(16) 0.1864(2) 0.15610(16) 0.0302(7) Uani 1 1 d . . .
H2A H 0.1786 0.1316 0.1522 0.036 Uiso 1 1 calc R . .
C2A C 0.12584(16) 0.4213(2) 0.34820(15) 0.0266(6) Uani 1 1 d . . .
H2AA H 0.1752 0.4270 0.3207 0.032 Uiso 1 1 calc R . .
C3 C 0.08377(17) 0.1927(2) 0.10073(16) 0.0313(7) Uani 1 1 d . . .
H3 H 0.0867 0.1429 0.0587 0.038 Uiso 1 1 calc R . .
C4 C 0.02448(16) 0.2716(2) 0.10638(14) 0.0278(6) Uani 1 1 d . . .
H4 H -0.0127 0.2769 0.0680 0.033 Uiso 1 1 calc R . .
C5 C -0.14977(15) 0.3905(2) 0.27410(17) 0.0302(7) Uani 1 1 d . . .
H5 H -0.1860 0.3911 0.2347 0.036 Uiso 1 1 calc R . .
C6 C -0.17278(16) 0.3724(2) 0.34744(17) 0.0313(7) Uani 1 1 d . . .
H6 H -0.2250 0.3602 0.3584 0.038 Uiso 1 1 calc R . .
C7 C -0.11995(16) 0.3721(2) 0.40439(16) 0.0300(7) Uani 1 1 d . . .
H7 H -0.1363 0.3604 0.4544 0.036 Uiso 1 1 calc R . .
C8 C -0.04322(16) 0.3886(2) 0.38960(15) 0.0275(6) Uani 1 1 d . . .
H8 H -0.0074 0.3883 0.4294 0.033 Uiso 1 1 calc R . .
C9 C 0.06294(14) 0.4241(2) 0.28850(14) 0.0222(6) Uani 1 1 d . . .
C10 C -0.04158(15) 0.4307(2) 0.18236(15) 0.0247(6) Uani 1 1 d . . .
H10 H -0.0816 0.4294 0.1427 0.030 Uiso 1 1 calc R . .
C11 C 0.07552(15) 0.3368(2) 0.22486(14) 0.0216(6) Uani 1 1 d . . .
C12 C 0.02017(15) 0.3423(2) 0.16859(14) 0.0223(6) Uani 1 1 d . . .
C14 C -0.01888(15) 0.4058(2) 0.31647(15) 0.0237(6) Uani 1 1 d . . .
C15 C -0.07366(15) 0.4074(2) 0.25927(15) 0.0242(6) Uani 1 1 d . . .
C16 C -0.00245(15) 0.5516(2) 0.18955(15) 0.0258(6) Uani 1 1 d . . .
H16A H -0.0406 0.6113 0.2045 0.031 Uiso 1 1 calc R . .
C17 C 0.06227(15) 0.5452(2) 0.24761(15) 0.0250(6) Uani 1 1 d . . .
H17A H 0.0562 0.6084 0.2852 0.030 Uiso 1 1 calc R . .
C18 C 0.03601(17) 0.5859(2) 0.11780(16) 0.0294(7) Uani 1 1 d . . .
C19 C 0.13392(16) 0.5648(2) 0.20204(16) 0.0264(6) Uani 1 1 d . . .
C20 C 0.16878(17) 0.5968(3) 0.06858(17) 0.0360(7) Uani 1 1 d . . .
H20A H 0.1422 0.6086 0.0211 0.054 Uiso 1 1 calc R . .
H20B H 0.2008 0.5278 0.0651 0.054 Uiso 1 1 calc R . .
H20C H 0.2006 0.6641 0.0794 0.054 Uiso 1 1 calc R . .
C21 C 0.12446(17) 0.5221(3) 0.40344(17) 0.0356(7) Uani 1 1 d . . .
H21A H 0.0724 0.5340 0.4214 0.053 Uiso 1 1 calc R . .
H21B H 0.1424 0.5923 0.3784 0.053 Uiso 1 1 calc R . .
H21C H 0.1578 0.5047 0.4459 0.053 Uiso 1 1 calc R . .
C22 C 0.19277(17) 0.2661(3) 0.41355(17) 0.0385(8) Uani 1 1 d . . .
C23 C 0.18737(19) 0.1520(3) 0.45215(19) 0.0496(9) Uani 1 1 d . . .
H23A H 0.2070 0.0914 0.4192 0.074 Uiso 1 1 calc R . .
H23B H 0.1341 0.1357 0.4643 0.074 Uiso 1 1 calc R . .
H23C H 0.2175 0.1540 0.4982 0.074 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C18 1.375(4) . ?
N1 C19 1.385(4) . ?
N1 C20 1.453(3) . ?
N2 C22 1.349(4) . ?
N2 C2A 1.467(3) . ?
N2 H2 0.8800 . ?
O1 C19 1.212(3) . ?
O2 C18 1.216(3) . ?
O3 C22 1.233(4) . ?
C1 C11 1.382(4) . ?
C1 C2 1.399(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(4) . ?
C2 H2A 0.9500 . ?
C2A C21 1.531(4) . ?
C2A C9 1.538(4) . ?
C2A H2AA 1.0000 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 C12 1.384(4) . ?
C4 H4 0.9500 . ?
C5 C15 1.379(4) . ?
C5 C6 1.389(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.379(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(4) . ?
C7 H7 0.9500 . ?
C8 C14 1.391(4) . ?
C8 H8 0.9500 . ?
C9 C14 1.538(4) . ?
C9 C11 1.540(4) . ?
C9 C17 1.583(4) . ?
C10 C15 1.512(4) . ?
C10 C12 1.513(4) . ?
C10 C16 1.567(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.402(4) . ?
C14 C15 1.406(4) . ?
C16 C18 1.505(4) . ?
C16 C17 1.543(4) . ?
C16 H16A 1.0000 . ?
C17 C19 1.518(4) . ?
C17 H17A 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.496(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C18 N1 C19 113.0(2) . . ?
C18 N1 C20 124.1(2) . . ?
C19 N1 C20 122.9(2) . . ?
C22 N2 C2A 120.7(2) . . ?
C22 N2 H2 119.7 . . ?
C2A N2 H2 119.7 . . ?
C11 C1 C2 119.7(3) . . ?
C11 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
N2 C2A C21 111.1(2) . . ?
N2 C2A C9 111.1(2) . . ?
C21 C2A C9 114.9(2) . . ?
N2 C2A H2AA 106.3 . . ?
C21 C2A H2AA 106.3 . . ?
C9 C2A H2AA 106.3 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C12 C4 C3 119.3(3) . . ?
C12 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C15 C5 C6 119.1(3) . . ?
C15 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.9(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C14 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C14 C8 H8 120.1 . . ?
C2A C9 C14 116.3(2) . . ?
C2A C9 C11 113.4(2) . . ?
C14 C9 C11 106.5(2) . . ?
C2A C9 C17 110.2(2) . . ?
C14 C9 C17 105.4(2) . . ?
C11 C9 C17 104.0(2) . . ?
C15 C10 C12 107.2(2) . . ?
C15 C10 C16 104.4(2) . . ?
C12 C10 C16 107.7(2) . . ?
C15 C10 H10 112.4 . . ?
C12 C10 H10 112.4 . . ?
C16 C10 H10 112.4 . . ?
C1 C11 C12 119.5(2) . . ?
C1 C11 C9 126.8(2) . . ?
C12 C11 C9 113.7(2) . . ?
C4 C12 C11 120.8(2) . . ?
C4 C12 C10 124.8(2) . . ?
C11 C12 C10 114.4(2) . . ?
C8 C14 C15 118.4(2) . . ?
C8 C14 C9 127.9(2) . . ?
C15 C14 C9 113.7(2) . . ?
C5 C15 C14 121.5(3) . . ?
C5 C15 C10 124.3(2) . . ?
C14 C15 C10 114.2(2) . . ?
C18 C16 C17 104.8(2) . . ?
C18 C16 C10 111.3(2) . . ?
C17 C16 C10 109.7(2) . . ?
C18 C16 H16A 110.3 . . ?
C17 C16 H16A 110.3 . . ?
C10 C16 H16A 110.3 . . ?
C19 C17 C16 104.1(2) . . ?
C19 C17 C9 112.0(2) . . ?
C16 C17 C9 111.1(2) . . ?
C19 C17 H17A 109.9 . . ?
C16 C17 H17A 109.9 . . ?
C9 C17 H17A 109.9 . . ?
O2 C18 N1 124.5(3) . . ?
O2 C18 C16 126.7(3) . . ?
N1 C18 C16 108.7(2) . . ?
O1 C19 N1 123.6(3) . . ?
O1 C19 C17 127.8(3) . . ?
N1 C19 C17 108.6(2) . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2A C21 H21A 109.5 . . ?
C2A C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2A C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 N2 121.9(3) . . ?
O3 C22 C23 122.0(3) . . ?
N2 C22 C23 116.1(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.055

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane / hexane'
