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

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

data_140905LT_a
_database_code_depnum_ccdc_archive 'CCDC 1027211'
_audit_update_record             
;
2014-10-01 deposited with the CCDC.
2015-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
"(S)-ethyl 1-oxo-2-phenethyl-3-thioxo-1,2,3,7,12,12a-hexahydroimidazo[1',5':1,7]azepino[4,5-b]indole-6-carboxylate"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 N3 O3 S'
_chemical_formula_weight         445.52

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'

_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                   12.6842(5)
_cell_length_b                   20.3035(8)
_cell_length_c                   8.2806(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.772(2)
_cell_angle_gamma                90
_cell_volume                     2101.59(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4870
_cell_measurement_theta_min      2.6900
_cell_measurement_theta_max      26.1290

_exptl_crystal_description       Monoclinic
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8830
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            15564
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         1.629
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_full        25.242
_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             4291
_reflns_number_gt                3541
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0923P)²+0.2124P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4291
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1514
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.28459(15) 0.42711(9) 0.3163(2) 0.0146(4) Uani 1 1 d . . . . .
C2 C 0.37071(15) 0.42704(9) 0.0790(2) 0.0132(4) Uani 1 1 d . . . . .
H2 H 0.4156 0.3929 0.1300 0.016 Uiso 1 1 calc R U . . .
C3 C 0.39494(14) 0.45104(9) -0.0626(2) 0.0127(4) Uani 1 1 d . . . . .
C4 C 0.34526(15) 0.50897(9) -0.1509(2) 0.0124(4) Uani 1 1 d . . . . .
C5 C 0.12238(16) 0.47531(10) 0.2164(2) 0.0161(4) Uani 1 1 d . . . . .
C6 C 0.31920(15) 0.58400(9) -0.3535(2) 0.0134(4) Uani 1 1 d . . . . .
C7 C 0.32247(16) 0.62041(10) -0.4970(2) 0.0165(4) Uani 1 1 d . . . . .
H7 H 0.3702 0.6094 -0.5697 0.020 Uiso 1 1 calc R U . . .
C8 C 0.25295(15) 0.67293(10) -0.5269(2) 0.0168(4) Uani 1 1 d . . . . .
H8 H 0.2522 0.6984 -0.6233 0.020 Uiso 1 1 calc R U . . .
C9 C 0.18319(16) 0.68981(10) -0.4186(2) 0.0191(4) Uani 1 1 d . . . . .
H9 H 0.1375 0.7269 -0.4419 0.023 Uiso 1 1 calc R U . . .
C10 C 0.18001(16) 0.65320(10) -0.2784(2) 0.0186(4) Uani 1 1 d . . . . .
H10 H 0.1323 0.6648 -0.2061 0.022 Uiso 1 1 calc R U . . .
C11 C 0.24859(15) 0.59856(9) -0.2448(2) 0.0148(4) Uani 1 1 d . . . . .
C12 C 0.26504(15) 0.55053(9) -0.1168(2) 0.0146(4) Uani 1 1 d . . . . .
C13 C 0.20309(16) 0.54750(9) 0.0209(2) 0.0161(4) Uani 1 1 d . . . . .
H13A H 0.1320 0.5677 -0.0149 0.019 Uiso 1 1 calc R U . . .
H13B H 0.2408 0.5737 0.1140 0.019 Uiso 1 1 calc R U . . .
C14 C 0.18804(15) 0.47759(10) 0.0790(2) 0.0156(4) Uani 1 1 d . . . . .
H14 H 0.1531 0.4500 -0.0151 0.019 Uiso 1 1 calc R U . . .
C15 C 0.15499(16) 0.43649(10) 0.5108(2) 0.0172(4) Uani 1 1 d . . . . .
H15A H 0.0986 0.4686 0.5252 0.021 Uiso 1 1 calc R U . . .
H15B H 0.2172 0.4443 0.5984 0.021 Uiso 1 1 calc R U . . .
C16 C 0.11282(17) 0.36635(10) 0.5268(2) 0.0205(5) Uani 1 1 d . . . . .
H16A H 0.0386 0.3634 0.4664 0.025 Uiso 1 1 calc R U . . .
H16B H 0.1572 0.3350 0.4759 0.025 Uiso 1 1 calc R U . . .
C17 C 0.11440(16) 0.34683(9) 0.7038(2) 0.0173(4) Uani 1 1 d . . . . .
C18 C 0.02275(17) 0.35048(10) 0.7745(2) 0.0208(5) Uani 1 1 d . . . . .
H18 H -0.0423 0.3656 0.7115 0.025 Uiso 1 1 calc R U . . .
C19 C 0.0258(2) 0.33208(10) 0.9371(3) 0.0267(5) Uani 1 1 d . . . . .
H19 H -0.0372 0.3347 0.9846 0.032 Uiso 1 1 calc R U . . .
C20 C 0.1203(2) 0.30988(10) 1.0301(2) 0.0283(5) Uani 1 1 d . . . . .
H20 H 0.1223 0.2975 1.1412 0.034 Uiso 1 1 calc R U . . .
C21 C 0.21173(19) 0.30582(10) 0.9605(2) 0.0267(5) Uani 1 1 d . . . . .
H21 H 0.2765 0.2900 1.0234 0.032 Uiso 1 1 calc R U . . .
C22 C 0.20895(17) 0.32481(10) 0.7988(2) 0.0212(5) Uani 1 1 d . . . . .
H22 H 0.2724 0.3227 0.7524 0.025 Uiso 1 1 calc R U . . .
C23 C 0.48223(15) 0.41590(9) -0.1266(2) 0.0131(4) Uani 1 1 d . . . . .
C24 C 0.58321(16) 0.31549(10) -0.1116(2) 0.0180(4) Uani 1 1 d . . . . .
H24A H 0.6274 0.2940 -0.0160 0.022 Uiso 1 1 calc R U . . .
H24B H 0.6307 0.3431 -0.1670 0.022 Uiso 1 1 calc R U . . .
C25 C 0.52972(19) 0.26391(11) -0.2284(2) 0.0254(5) Uani 1 1 d . . . . .
H25A H 0.4755 0.2408 -0.1784 0.038 Uiso 1 1 calc R U . . .
H25B H 0.5833 0.2323 -0.2525 0.038 Uiso 1 1 calc R U . . .
H25C H 0.4955 0.2851 -0.3303 0.038 Uiso 1 1 calc R U . . .
N1 N 0.28862(12) 0.44640(8) 0.15754(18) 0.0137(4) Uani 1 1 d . . . . .
N2 N 0.18690(13) 0.44676(8) 0.35115(18) 0.0157(4) Uani 1 1 d . . . . .
N3 N 0.37735(13) 0.52971(8) -0.29409(18) 0.0137(3) Uani 1 1 d . . . . .
H3 H 0.4274 0.5109 -0.3400 0.016 Uiso 1 1 calc R U . . .
O1 O 0.03200(11) 0.49503(7) 0.21324(16) 0.0223(3) Uani 1 1 d . . . . .
O2 O 0.53065(11) 0.43728(7) -0.23014(15) 0.0154(3) Uani 1 1 d . . . . .
O3 O 0.50184(11) 0.35641(7) -0.05729(16) 0.0187(3) Uani 1 1 d . . . . .
S1 S 0.37874(4) 0.38866(3) 0.44123(6) 0.02125(18) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.378(2) . ?
C1 N1 1.381(2) . ?
C1 S1 1.6391(19) . ?
C2 C3 1.352(3) . ?
C2 N1 1.376(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.470(2) . ?
C3 C23 1.489(3) . ?
C4 N3 1.383(2) . ?
C4 C12 1.388(3) . ?
C5 O1 1.210(2) . ?
C5 N2 1.393(2) . ?
C5 C14 1.521(3) . ?
C6 N3 1.370(2) . ?
C6 C11 1.405(3) . ?
C6 C7 1.406(3) . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.405(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.408(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.429(3) . ?
C12 C13 1.492(3) . ?
C13 C14 1.521(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N1 1.473(2) . ?
C14 H14 1.0000 . ?
C15 N2 1.462(2) . ?
C15 C16 1.535(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.516(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.389(3) . ?
C17 C22 1.392(3) . ?
C18 C19 1.392(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 O2 1.216(2) . ?
C23 O3 1.342(2) . ?
C24 O3 1.454(2) . ?
C24 C25 1.507(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N3 H3 0.8800 . ?

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
N2 C1 N1 107.29(15) . . ?
N2 C1 S1 126.18(14) . . ?
N1 C1 S1 126.53(15) . . ?
C3 C2 N1 127.50(17) . . ?
C3 C2 H2 116.2 . . ?
N1 C2 H2 116.2 . . ?
C2 C3 C4 125.37(17) . . ?
C2 C3 C23 115.38(16) . . ?
C4 C3 C23 119.21(16) . . ?
N3 C4 C12 108.81(16) . . ?
N3 C4 C3 120.46(17) . . ?
C12 C4 C3 130.72(17) . . ?
O1 C5 N2 125.49(18) . . ?
O1 C5 C14 127.64(17) . . ?
N2 C5 C14 106.86(16) . . ?
N3 C6 C11 107.60(16) . . ?
N3 C6 C7 129.41(18) . . ?
C11 C6 C7 122.98(18) . . ?
C8 C7 C6 116.66(18) . . ?
C8 C7 H7 121.7 . . ?
C6 C7 H7 121.7 . . ?
C7 C8 C9 121.78(17) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C10 C9 C8 121.02(18) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 118.93(19) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C6 C11 C10 118.61(17) . . ?
C6 C11 C12 107.63(17) . . ?
C10 C11 C12 133.76(19) . . ?
C4 C12 C11 106.47(16) . . ?
C4 C12 C13 129.08(17) . . ?
C11 C12 C13 124.43(17) . . ?
C12 C13 C14 113.00(16) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N1 C14 C13 113.26(16) . . ?
N1 C14 C5 101.52(14) . . ?
C13 C14 C5 112.27(16) . . ?
N1 C14 H14 109.8 . . ?
C13 C14 H14 109.8 . . ?
C5 C14 H14 109.8 . . ?
N2 C15 C16 111.36(15) . . ?
N2 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N2 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 112.23(15) . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C22 118.78(18) . . ?
C18 C17 C16 121.26(19) . . ?
C22 C17 C16 119.96(19) . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.72(19) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.0(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.9(2) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
O2 C23 O3 122.93(18) . . ?
O2 C23 C3 125.12(17) . . ?
O3 C23 C3 111.95(16) . . ?
O3 C24 C25 109.26(17) . . ?
O3 C24 H24A 109.8 . . ?
C25 C24 H24A 109.8 . . ?
O3 C24 H24B 109.8 . . ?
C25 C24 H24B 109.8 . . ?
H24A C24 H24B 108.3 . . ?
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 . . ?
C2 N1 C1 121.51(16) . . ?
C2 N1 C14 125.61(15) . . ?
C1 N1 C14 111.91(15) . . ?
C1 N2 C5 112.31(15) . . ?
C1 N2 C15 123.02(16) . . ?
C5 N2 C15 124.64(17) . . ?
C6 N3 C4 109.49(16) . . ?
C6 N3 H3 125.3 . . ?
C4 N3 H3 125.3 . . ?
C23 O3 C24 118.12(15) . . ?

_refine_diff_density_max         0.530
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.138

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_cu_140906lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1028024'
_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2015-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        PD-N4-17
_chemical_name_common            
"(S)-ethyl 2-(4-chlorophenyl)-1,3-dioxo-1,2,3,7,12,12a-hexahydroimidazo[1',5':1,7]azepino[4,5-b]indole-6-carboxylate"
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 Cl N3 O4'
_chemical_formula_weight         433.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   6.6540(3)
_cell_length_b                   12.6487(7)
_cell_length_c                   23.3926(13)
_cell_angle_alpha                90
_cell_angle_beta                 97.152(3)
_cell_angle_gamma                90
_cell_volume                     1953.51(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4495
_cell_measurement_theta_min      3.8089
_cell_measurement_theta_max      66.4034

_exptl_crystal_description       Acicular
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    2.058
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4939
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            12712
_diffrn_reflns_av_unetI/netI     0.0805
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.809
_diffrn_reflns_theta_max         66.826
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             3385
_reflns_number_gt                2165
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.1412P)²+1.5598P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3385
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0852
_refine_ls_wR_factor_ref         0.2862
_refine_ls_wR_factor_gt          0.2415
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_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 0.1805(3) -0.45028(15) 1.06141(8) 0.0953(7) Uani 1 1 d . . . . .
O1 O 0.2237(4) 0.1255(3) 0.69955(14) 0.0535(9) Uani 1 1 d . . . . .
O2 O 0.7333(5) -0.0581(3) 0.98215(17) 0.0755(13) Uani 1 1 d . . . . .
O3 O 0.4614(5) 0.2442(3) 0.68547(15) 0.0559(9) Uani 1 1 d . . . . .
O4 O 0.1963(4) -0.1036(3) 0.84264(14) 0.0544(9) Uani 1 1 d . . . . .
N1 N 0.4702(6) 0.0093(4) 0.84837(18) 0.0570(12) Uani 1 1 d . . . . .
N2 N 0.4454(6) -0.1025(3) 0.92096(18) 0.0527(11) Uani 1 1 d . . . . .
N3 N 0.7940(6) 0.2591(3) 0.76266(18) 0.0530(11) Uani 1 1 d . . . . .
H5 H 0.7341 0.2916 0.7319 0.064 Uiso 1 1 calc R U . . .
C1 C -0.0972(7) 0.1051(4) 0.6451(2) 0.0554(13) Uani 1 1 d . . . . .
H1 H -0.0686 0.0307 0.6376 0.083 Uiso 1 1 calc R U . . .
H13 H -0.1924 0.1331 0.6133 0.083 Uiso 1 1 calc R U . . .
H14 H -0.1569 0.1107 0.6812 0.083 Uiso 1 1 calc R U . . .
C2 C 0.0968(6) 0.1676(4) 0.6498(2) 0.0532(13) Uani 1 1 d . . . . .
H11 H 0.1636 0.1592 0.6146 0.064 Uiso 1 1 calc R U . . .
H12 H 0.0696 0.2437 0.6553 0.064 Uiso 1 1 calc R U . . .
C3 C 0.4037(7) 0.1741(4) 0.7143(2) 0.0474(12) Uani 1 1 d . . . . .
C4 C 0.5136(6) 0.1312(4) 0.7688(2) 0.0473(12) Uani 1 1 d . . . . .
C5 C 0.4160(7) 0.0574(4) 0.7958(2) 0.0501(12) Uani 1 1 d . . . . .
H4 H 0.2905 0.0347 0.7757 0.060 Uiso 1 1 calc R U . . .
C6 C 0.3505(7) -0.0694(4) 0.8673(2) 0.0503(12) Uani 1 1 d . . . . .
C7 C 0.3752(7) -0.1874(4) 0.9533(2) 0.0487(12) Uani 1 1 d . . . . .
C8 C 0.5045(7) -0.2713(4) 0.9682(2) 0.0533(13) Uani 1 1 d . . . . .
H2 H 0.6345 -0.2726 0.9554 0.064 Uiso 1 1 calc R U . . .
C9 C 0.4464(8) -0.3529(4) 1.0013(2) 0.0595(14) Uani 1 1 d . . . . .
H3 H 0.5352 -0.4101 1.0125 0.071 Uiso 1 1 calc R U . . .
C10 C 0.2528(8) -0.3485(5) 1.0179(2) 0.0658(16) Uani 1 1 d . . . . .
C11 C 0.6196(8) -0.0447(5) 0.9385(3) 0.0716(18) Uani 1 1 d . . . . .
C12 C 0.6317(9) 0.0412(6) 0.8941(3) 0.091(2) Uani 1 1 d . . . . .
C13 C 0.7127(6) 0.1756(4) 0.7900(2) 0.0475(12) Uani 1 1 d . . . . .
C14 C 0.9819(7) 0.2840(4) 0.7904(2) 0.0498(12) Uani 1 1 d . . . . .
C15 C 1.0174(7) 0.2157(4) 0.8379(2) 0.0523(13) Uani 1 1 d . . . . .
C16 C 0.8454(7) 0.1468(5) 0.8368(2) 0.0569(14) Uani 1 1 d . . . . .
C17 C 0.8276(9) 0.0567(7) 0.8774(3) 0.098(3) Uani 1 1 d . . . . .
H6 H 0.9395 0.0130 0.8910 0.117 Uiso 1 1 calc R U . . .
C18 C 1.2008(7) 0.2263(5) 0.8751(2) 0.0571(14) Uani 1 1 d . . . . .
H10 H 1.2274 0.1836 0.9085 0.069 Uiso 1 1 calc R U . . .
C19 C 1.3405(7) 0.3001(4) 0.8616(2) 0.0537(13) Uani 1 1 d . . . . .
H9 H 1.4649 0.3073 0.8860 0.064 Uiso 1 1 calc R U . . .
C20 C 1.3033(7) 0.3638(4) 0.8132(2) 0.0558(13) Uani 1 1 d . . . . .
H8 H 1.4044 0.4121 0.8045 0.067 Uiso 1 1 calc R U . . .
C21 C 1.1229(7) 0.3583(4) 0.7776(2) 0.0556(13) Uani 1 1 d . . . . .
H7 H 1.0958 0.4040 0.7453 0.067 Uiso 1 1 calc R U . . .
C22 C 0.1821(7) -0.1845(5) 0.9703(2) 0.0590(14) Uani 1 1 d . . . . .
H16 H 0.0938 -0.1268 0.9596 0.071 Uiso 1 1 calc R U . . .
C23 C 0.1210(8) -0.2667(5) 1.0029(2) 0.0641(15) Uani 1 1 d . . . . .
H15 H -0.0103 -0.2667 1.0148 0.077 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 C10 1.745(6) . ?
O1 C3 1.352(6) . ?
O1 C2 1.451(5) . ?
O2 C11 1.205(6) . ?
O3 C3 1.206(6) . ?
O4 C6 1.193(6) . ?
N1 C5 1.380(6) . ?
N1 C6 1.382(7) . ?
N1 C12 1.475(6) . ?
N2 C11 1.389(6) . ?
N2 C6 1.398(6) . ?
N2 C7 1.426(7) . ?
N3 C14 1.372(6) . ?
N3 C13 1.379(6) . ?
N3 H5 0.8800 . ?
C1 C2 1.506(7) . ?
C1 H1 0.9800 . ?
C1 H13 0.9800 . ?
C1 H14 0.9800 . ?
C2 H11 0.9900 . ?
C2 H12 0.9900 . ?
C3 C4 1.490(7) . ?
C4 C5 1.339(7) . ?
C4 C13 1.467(6) . ?
C5 H4 0.9500 . ?
C7 C8 1.383(7) . ?
C7 C22 1.391(6) . ?
C8 C9 1.374(7) . ?
C8 H2 0.9500 . ?
C9 C10 1.392(7) . ?
C9 H3 0.9500 . ?
C10 C23 1.373(8) . ?
C11 C12 1.511(8) . ?
C12 C17 1.421(9) . ?
C13 C16 1.369(6) . ?
C14 C21 1.387(7) . ?
C14 C15 1.404(7) . ?
C15 C18 1.413(6) . ?
C15 C16 1.436(7) . ?
C16 C17 1.497(8) . ?
C17 H6 0.9500 . ?
C18 C19 1.381(7) . ?
C18 H10 0.9500 . ?
C19 C20 1.386(8) . ?
C19 H9 0.9500 . ?
C20 C21 1.374(7) . ?
C20 H8 0.9500 . ?
C21 H7 0.9500 . ?
C22 C23 1.381(8) . ?
C22 H16 0.9500 . ?
C23 H15 0.9500 . ?

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
C3 O1 C2 116.6(4) . . ?
C5 N1 C6 120.4(4) . . ?
C5 N1 C12 127.8(4) . . ?
C6 N1 C12 111.2(4) . . ?
C11 N2 C6 112.0(4) . . ?
C11 N2 C7 123.8(4) . . ?
C6 N2 C7 124.2(4) . . ?
C14 N3 C13 110.1(4) . . ?
C14 N3 H5 124.9 . . ?
C13 N3 H5 124.9 . . ?
C2 C1 H1 109.5 . . ?
C2 C1 H13 109.5 . . ?
H1 C1 H13 109.5 . . ?
C2 C1 H14 109.5 . . ?
H1 C1 H14 109.5 . . ?
H13 C1 H14 109.5 . . ?
O1 C2 C1 106.0(4) . . ?
O1 C2 H11 110.5 . . ?
C1 C2 H11 110.5 . . ?
O1 C2 H12 110.5 . . ?
C1 C2 H12 110.5 . . ?
H11 C2 H12 108.7 . . ?
O3 C3 O1 121.6(4) . . ?
O3 C3 C4 126.1(4) . . ?
O1 C3 C4 112.2(4) . . ?
C5 C4 C13 125.3(4) . . ?
C5 C4 C3 116.2(4) . . ?
C13 C4 C3 118.4(4) . . ?
C4 C5 N1 129.7(4) . . ?
C4 C5 H4 115.1 . . ?
N1 C5 H4 115.1 . . ?
O4 C6 N1 127.0(5) . . ?
O4 C6 N2 126.2(5) . . ?
N1 C6 N2 106.8(4) . . ?
C8 C7 C22 121.1(5) . . ?
C8 C7 N2 118.5(4) . . ?
C22 C7 N2 120.4(5) . . ?
C9 C8 C7 120.5(5) . . ?
C9 C8 H2 119.7 . . ?
C7 C8 H2 119.7 . . ?
C8 C9 C10 117.5(5) . . ?
C8 C9 H3 121.2 . . ?
C10 C9 H3 121.2 . . ?
C23 C10 C9 122.8(5) . . ?
C23 C10 Cl1 119.4(5) . . ?
C9 C10 Cl1 117.7(5) . . ?
O2 C11 N2 126.1(5) . . ?
O2 C11 C12 127.0(5) . . ?
N2 C11 C12 106.8(4) . . ?
C17 C12 N1 116.7(6) . . ?
C17 C12 C11 114.7(6) . . ?
N1 C12 C11 101.9(4) . . ?
C16 C13 N3 108.9(4) . . ?
C16 C13 C4 129.3(5) . . ?
N3 C13 C4 121.8(4) . . ?
N3 C14 C21 130.9(5) . . ?
N3 C14 C15 106.7(4) . . ?
C21 C14 C15 122.4(4) . . ?
C14 C15 C18 118.4(5) . . ?
C14 C15 C16 107.7(4) . . ?
C18 C15 C16 133.9(5) . . ?
C13 C16 C15 106.6(5) . . ?
C13 C16 C17 128.0(5) . . ?
C15 C16 C17 125.2(4) . . ?
C12 C17 C16 115.3(6) . . ?
C12 C17 H6 122.3 . . ?
C16 C17 H6 122.3 . . ?
C19 C18 C15 118.6(5) . . ?
C19 C18 H10 120.7 . . ?
C15 C18 H10 120.7 . . ?
C18 C19 C20 121.5(5) . . ?
C18 C19 H9 119.3 . . ?
C20 C19 H9 119.3 . . ?
C21 C20 C19 121.3(5) . . ?
C21 C20 H8 119.4 . . ?
C19 C20 H8 119.4 . . ?
C20 C21 C14 117.8(5) . . ?
C20 C21 H7 121.1 . . ?
C14 C21 H7 121.1 . . ?
C23 C22 C7 118.9(5) . . ?
C23 C22 H16 120.6 . . ?
C7 C22 H16 120.6 . . ?
C10 C23 C22 119.1(5) . . ?
C10 C23 H15 120.5 . . ?
C22 C23 H15 120.5 . . ?

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.093

_shelxl_version_number           2014/6



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_cu_140110_0m
_database_code_depnum_ccdc_archive 'CCDC 1033162'
_audit_update_record             
;
2014-11-07 deposited with the CCDC.
2015-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'(S)-5-ethyl 2-methyl 1, 2, 3, 6 -tetrahydroazepino[4,5-b]indole-2,5-dicarboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N2 O4'
_chemical_formula_weight         314.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   7.9602(7)
_cell_length_b                   8.6689(7)
_cell_length_c                   11.7774(11)
_cell_angle_alpha                94.238(5)
_cell_angle_beta                 97.302(6)
_cell_angle_gamma                96.834(5)
_cell_volume                     797.12(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6638
_cell_measurement_theta_min      5.1610
_cell_measurement_theta_max      66.2850

_exptl_crystal_description       lump
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.778
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6197
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            8958
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.160
_diffrn_reflns_theta_max         66.403
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.938
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.938
_reflns_number_total             4412
_reflns_number_gt                4028
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.938


_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1513P)²+0.0470P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4412
_refine_ls_number_parameters     420
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.2031
_refine_ls_wR_factor_gt          0.1953
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9366(6) 0.0470(6) 0.2219(4) 0.0533(11) Uani 1 1 d . . . . .
C2 C 0.9544(5) 0.1576(5) 0.3223(4) 0.0519(11) Uani 1 1 d . . . . .
C3 C 1.0412(6) 0.3859(6) 0.4287(5) 0.0575(12) Uani 1 1 d . . . . .
C4 C 1.1152(7) 0.5370(6) 0.4723(6) 0.0697(14) Uani 1 1 d . . . . .
H4 H 1.1768 0.6013 0.4281 0.084 Uiso 1 1 calc R U . . .
C5 C 1.0941(8) 0.5870(7) 0.5815(6) 0.0749(16) Uani 1 1 d . . . . .
H5 H 1.1422 0.6868 0.6121 0.090 Uiso 1 1 calc R U . . .
C6 C 1.0013(8) 0.4909(7) 0.6483(6) 0.0777(16) Uani 1 1 d . . . . .
H6 H 0.9897 0.5276 0.7228 0.093 Uiso 1 1 calc R U . . .
C7 C 0.9264(7) 0.3421(7) 0.6055(5) 0.0686(14) Uani 1 1 d . . . . .
H7 H 0.8631 0.2799 0.6500 0.082 Uiso 1 1 calc R U . . .
C8 C 0.9474(6) 0.2874(6) 0.4954(5) 0.0559(11) Uani 1 1 d . . . . .
C9 C 0.8926(5) 0.1431(5) 0.4244(4) 0.0517(10) Uani 1 1 d . . . . .
C10 C 0.7800(6) 0.0077(6) 0.4572(5) 0.0603(12) Uani 1 1 d . . . . .
H10A H 0.6641 0.0113 0.4214 0.072 Uiso 1 1 calc R U . . .
H10B H 0.7803 0.0190 0.5398 0.072 Uiso 1 1 calc R U . . .
C11 C 0.8308(6) -0.1512(5) 0.4239(4) 0.0543(10) Uani 1 1 d . . . . .
H11 H 0.9478 -0.1553 0.4601 0.065 Uiso 1 1 calc R U . . .
C12 C 0.8700(8) -0.1065(7) 0.2192(5) 0.0658(13) Uani 1 1 d . . . . .
H12 H 0.8568 -0.1618 0.1472 0.079 Uiso 1 1 calc R U . . .
C13 C 0.9839(6) 0.1002(7) 0.1143(5) 0.0594(12) Uani 1 1 d . . . . .
C14 C 0.9885(10) 0.0387(10) -0.0830(6) 0.089(2) Uani 1 1 d . . . . .
H14A H 0.9457 0.1364 -0.0983 0.107 Uiso 1 1 calc R U . . .
H14B H 1.1117 0.0544 -0.0806 0.107 Uiso 1 1 calc R U . . .
C15 C 0.917(2) -0.076(2) -0.1698(9) 0.188(7) Uani 1 1 d . . . . .
H15A H 0.7966 -0.0722 -0.1855 0.282 Uiso 1 1 calc R U . . .
H15B H 0.9376 -0.1762 -0.1461 0.282 Uiso 1 1 calc R U . . .
H15C H 0.9686 -0.0578 -0.2380 0.282 Uiso 1 1 calc R U . . .
C16 C 0.7110(6) -0.2763(6) 0.4689(5) 0.0591(11) Uani 1 1 d . . . . .
C17 C 0.5895(9) -0.3633(10) 0.6267(6) 0.089(2) Uani 1 1 d . . . . .
H17A H 0.6219 -0.4656 0.6135 0.134 Uiso 1 1 calc R U . . .
H17B H 0.4746 -0.3621 0.5905 0.134 Uiso 1 1 calc R U . . .
H17C H 0.5960 -0.3365 0.7078 0.134 Uiso 1 1 calc R U . . .
C18 C 0.3906(5) 0.0959(6) 0.3257(4) 0.0513(10) Uani 1 1 d . . . . .
C19 C 0.3740(5) -0.0128(5) 0.2238(4) 0.0497(10) Uani 1 1 d . . . . .
C20 C 0.3222(6) -0.2482(6) 0.1220(5) 0.0582(12) Uani 1 1 d . . . . .
C21 C 0.2757(9) -0.4050(7) 0.0830(6) 0.0758(16) Uani 1 1 d . . . . .
H21 H 0.2398 -0.4772 0.1323 0.091 Uiso 1 1 calc R U . . .
C22 C 0.2842(9) -0.4498(7) -0.0287(6) 0.0791(17) Uani 1 1 d . . . . .
H22 H 0.2538 -0.5543 -0.0555 0.095 Uiso 1 1 calc R U . . .
C23 C 0.3369(9) -0.3437(8) -0.1044(6) 0.0784(16) Uani 1 1 d . . . . .
H23 H 0.3429 -0.3783 -0.1803 0.094 Uiso 1 1 calc R U . . .
C24 C 0.3807(8) -0.1863(7) -0.0670(5) 0.0701(14) Uani 1 1 d . . . . .
H24 H 0.4155 -0.1152 -0.1174 0.084 Uiso 1 1 calc R U . . .
C25 C 0.3717(6) -0.1366(6) 0.0474(5) 0.0567(11) Uani 1 1 d . . . . .
C26 C 0.4010(6) 0.0120(6) 0.1139(4) 0.0530(10) Uani 1 1 d . . . . .
C27 C 0.4544(7) 0.1650(5) 0.0692(4) 0.0581(11) Uani 1 1 d . . . . .
H27A H 0.3557 0.2203 0.0558 0.070 Uiso 1 1 calc R U . . .
H27B H 0.4958 0.1458 -0.0039 0.070 Uiso 1 1 calc R U . . .
C28 C 0.5933(6) 0.2672(5) 0.1516(4) 0.0510(10) Uani 1 1 d . . . . .
H28 H 0.6827 0.2028 0.1748 0.061 Uiso 1 1 calc R U . . .
C29 C 0.4603(6) 0.2493(6) 0.3314(4) 0.0534(11) Uani 1 1 d . . . . .
H29 H 0.4544 0.3079 0.3998 0.064 Uiso 1 1 calc R U . . .
C30 C 0.3333(6) 0.0406(6) 0.4310(4) 0.0550(11) Uani 1 1 d . . . . .
C31 C 0.3119(9) 0.1058(9) 0.6268(6) 0.0795(17) Uani 1 1 d . . . . .
H31A H 0.3619 0.0130 0.6466 0.095 Uiso 1 1 calc R U . . .
H31B H 0.1886 0.0822 0.6205 0.095 Uiso 1 1 calc R U . . .
C32 C 0.3732(15) 0.2341(12) 0.7165(7) 0.113(3) Uani 1 1 d . . . . .
H32A H 0.3262 0.3265 0.6952 0.169 Uiso 1 1 calc R U . . .
H32B H 0.4956 0.2535 0.7249 0.169 Uiso 1 1 calc R U . . .
H32C H 0.3379 0.2062 0.7880 0.169 Uiso 1 1 calc R U . . .
C33 C 0.6764(6) 0.4066(6) 0.0969(5) 0.0578(11) Uani 1 1 d . . . . .
C34 C 0.7849(11) 0.4945(10) -0.0648(7) 0.103(3) Uani 1 1 d . . . . .
H34A H 0.8954 0.5300 -0.0221 0.155 Uiso 1 1 calc R U . . .
H34B H 0.7179 0.5795 -0.0680 0.155 Uiso 1 1 calc R U . . .
H34C H 0.7978 0.4563 -0.1414 0.155 Uiso 1 1 calc R U . . .
N1 N 1.0432(5) 0.3065(5) 0.3262(4) 0.0595(10) Uani 1 1 d . . . . .
H1 H 1.0923 0.3428 0.2710 0.071 Uiso 1 1 calc R U . . .
N2 N 0.8211(8) -0.1894(6) 0.3019(5) 0.0809(16) Uani 1 1 d . . . . .
H2 H 0.7752 -0.2831 0.2786 0.097 Uiso 1 1 calc R U . . .
N3 N 0.3244(6) -0.1719(5) 0.2276(4) 0.0611(10) Uani 1 1 d . . . . .
H3 H 0.2991 -0.2154 0.2876 0.073 Uiso 1 1 calc R U . . .
N4 N 0.5358(6) 0.3281(5) 0.2533(4) 0.0611(10) Uani 1 1 d . . . . .
H4A H 0.5512 0.4280 0.2665 0.073 Uiso 1 1 calc R U . . .
O1 O 1.0497(6) 0.2321(5) 0.1034(4) 0.0740(11) Uani 1 1 d . . . . .
O2 O 0.9460(6) -0.0069(6) 0.0246(4) 0.0783(12) Uani 1 1 d . . . . .
O3 O 0.6291(7) -0.3859(5) 0.4091(4) 0.0895(15) Uani 1 1 d . . . . .
O4 O 0.7043(5) -0.2506(5) 0.5786(3) 0.0698(10) Uani 1 1 d . . . . .
O5 O 0.2721(6) -0.0915(5) 0.4421(4) 0.0749(11) Uani 1 1 d . . . . .
O6 O 0.3589(5) 0.1509(5) 0.5199(4) 0.0702(10) Uani 1 1 d . . . . .
O7 O 0.7214(7) 0.5322(5) 0.1477(4) 0.0871(14) Uani 1 1 d . . . . .
O8 O 0.6999(5) 0.3702(5) -0.0088(4) 0.0731(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C12 1.369(8) . ?
C1 C2 1.448(7) . ?
C1 C13 1.457(7) . ?
C2 C9 1.365(7) . ?
C2 N1 1.391(6) . ?
C3 N1 1.347(7) . ?
C3 C4 1.403(8) . ?
C3 C8 1.415(7) . ?
C4 C5 1.364(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.441(7) . ?
C9 C10 1.495(6) . ?
C10 C11 1.519(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.441(7) . ?
C11 C16 1.527(6) . ?
C11 H11 0.9800 . ?
C12 N2 1.322(8) . ?
C12 H12 0.9300 . ?
C13 O1 1.223(7) . ?
C13 O2 1.332(8) . ?
C14 C15 1.385(14) . ?
C14 O2 1.425(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O3 1.209(7) . ?
C16 O4 1.304(7) . ?
C17 O4 1.453(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C29 1.372(7) . ?
C18 C19 1.452(7) . ?
C18 C30 1.468(7) . ?
C19 C26 1.367(7) . ?
C19 N3 1.395(6) . ?
C20 N3 1.361(8) . ?
C20 C21 1.393(8) . ?
C20 C25 1.409(7) . ?
C21 C22 1.356(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.393(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.392(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.396(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.436(7) . ?
C26 C27 1.497(6) . ?
C27 C28 1.523(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 N4 1.424(7) . ?
C28 C33 1.532(6) . ?
C28 H28 0.9800 . ?
C29 N4 1.344(6) . ?
C29 H29 0.9300 . ?
C30 O5 1.213(6) . ?
C30 O6 1.342(7) . ?
C31 O6 1.427(7) . ?
C31 C32 1.469(11) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 O7 1.195(7) . ?
C33 O8 1.303(7) . ?
C34 O8 1.449(7) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
N1 H1 0.8600 . ?
N2 H2 0.8600 . ?
N3 H3 0.8600 . ?
N4 H4A 0.8600 . ?

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
C12 C1 C2 123.9(5) . . ?
C12 C1 C13 116.6(5) . . ?
C2 C1 C13 119.4(4) . . ?
C9 C2 N1 108.1(4) . . ?
C9 C2 C1 130.0(4) . . ?
N1 C2 C1 122.0(4) . . ?
N1 C3 C4 130.8(5) . . ?
N1 C3 C8 107.9(4) . . ?
C4 C3 C8 121.3(5) . . ?
C5 C4 C3 118.0(6) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C4 C5 C6 121.2(6) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 121.1(6) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C6 119.0(6) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C3 119.3(5) . . ?
C7 C8 C9 134.6(5) . . ?
C3 C8 C9 106.1(5) . . ?
C2 C9 C8 107.6(4) . . ?
C2 C9 C10 127.4(5) . . ?
C8 C9 C10 124.8(5) . . ?
C9 C10 C11 114.8(4) . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
N2 C11 C10 114.5(4) . . ?
N2 C11 C16 107.1(4) . . ?
C10 C11 C16 108.7(4) . . ?
N2 C11 H11 108.8 . . ?
C10 C11 H11 108.8 . . ?
C16 C11 H11 108.8 . . ?
N2 C12 C1 130.8(5) . . ?
N2 C12 H12 114.6 . . ?
C1 C12 H12 114.6 . . ?
O1 C13 O2 121.0(5) . . ?
O1 C13 C1 124.5(5) . . ?
O2 C13 C1 114.5(5) . . ?
C15 C14 O2 109.8(8) . . ?
C15 C14 H14A 109.7 . . ?
O2 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
O2 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 O4 123.5(5) . . ?
O3 C16 C11 123.8(5) . . ?
O4 C16 C11 112.7(4) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C29 C18 C19 124.0(5) . . ?
C29 C18 C30 116.8(5) . . ?
C19 C18 C30 119.2(4) . . ?
C26 C19 N3 108.1(4) . . ?
C26 C19 C18 130.6(4) . . ?
N3 C19 C18 121.3(4) . . ?
N3 C20 C21 130.7(5) . . ?
N3 C20 C25 107.8(4) . . ?
C21 C20 C25 121.4(6) . . ?
C22 C21 C20 118.4(6) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C21 C22 C23 121.9(6) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C24 C23 C22 120.3(6) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.1(6) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C24 C25 C20 118.9(5) . . ?
C24 C25 C26 134.5(5) . . ?
C20 C25 C26 106.6(5) . . ?
C19 C26 C25 107.7(4) . . ?
C19 C26 C27 127.0(5) . . ?
C25 C26 C27 125.2(5) . . ?
C26 C27 C28 112.6(4) . . ?
C26 C27 H27A 109.1 . . ?
C28 C27 H27A 109.1 . . ?
C26 C27 H27B 109.1 . . ?
C28 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
N4 C28 C27 113.8(4) . . ?
N4 C28 C33 106.9(4) . . ?
C27 C28 C33 113.0(4) . . ?
N4 C28 H28 107.6 . . ?
C27 C28 H28 107.6 . . ?
C33 C28 H28 107.6 . . ?
N4 C29 C18 130.1(5) . . ?
N4 C29 H29 115.0 . . ?
C18 C29 H29 115.0 . . ?
O5 C30 O6 120.8(5) . . ?
O5 C30 C18 125.7(5) . . ?
O6 C30 C18 113.6(4) . . ?
O6 C31 C32 109.1(6) . . ?
O6 C31 H31A 109.9 . . ?
C32 C31 H31A 109.9 . . ?
O6 C31 H31B 109.9 . . ?
C32 C31 H31B 109.9 . . ?
H31A C31 H31B 108.3 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O7 C33 O8 124.2(5) . . ?
O7 C33 C28 123.4(5) . . ?
O8 C33 C28 112.3(4) . . ?
O8 C34 H34A 109.5 . . ?
O8 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O8 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C3 N1 C2 110.4(4) . . ?
C3 N1 H1 124.8 . . ?
C2 N1 H1 124.8 . . ?
C12 N2 C11 131.7(5) . . ?
C12 N2 H2 114.1 . . ?
C11 N2 H2 114.1 . . ?
C20 N3 C19 109.8(4) . . ?
C20 N3 H3 125.1 . . ?
C19 N3 H3 125.1 . . ?
C29 N4 C28 128.3(4) . . ?
C29 N4 H4A 115.9 . . ?
C28 N4 H4A 115.9 . . ?
C13 O2 C14 117.0(5) . . ?
C16 O4 C17 115.6(5) . . ?
C30 O6 C31 117.3(5) . . ?
C33 O8 C34 115.6(5) . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
