# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_iabne1
_database_code_depnum_ccdc_archive 'CCDC 960921'
_audit_update_record             
;
2013-09-13 deposited with the CCDC.
2015-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 Ethyl(2R,3aR,10bR)-1-benzyl-10-chloro-1,2,3,3a,4,10b-hexadydropyrrolo-
[2'3':3,4]pyrrolo[1,2-a]indole-2-carboxylate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 Cl N2 O2'
_chemical_formula_sum            'C23 H23 Cl N2 O2'
_chemical_formula_weight         394.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2721(7)
_cell_length_b                   10.3272(6)
_cell_length_c                   10.7817(7)
_cell_angle_alpha                81.614(5)
_cell_angle_beta                 81.335(6)
_cell_angle_gamma                89.456(5)
_cell_volume                     1009.62(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1820
_cell_measurement_theta_min      3.8450
_cell_measurement_theta_max      25.7300

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_min  0.52203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7318
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3954
_reflns_number_gt                1914
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  PLATON(Spek,2009)

_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)+(0.0494P)²+0.0000P] 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         3954
_refine_ls_number_parameters     262
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1606
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.02359(10) 1.06887(9) 0.30672(9) 0.0726(3) Uani 1 1 d . . .
O1 O 0.8947(3) 0.5086(3) 0.3136(3) 0.1286(14) Uani 1 1 d . . .
O2 O 0.6960(3) 0.4167(2) 0.4301(2) 0.0791(8) Uani 1 1 d D . .
N1 N 0.7508(3) 0.7597(2) 0.3454(2) 0.0489(6) Uani 1 1 d . A .
C2 C 0.6746(3) 0.6369(3) 0.3426(3) 0.0565(8) Uani 1 1 d . . .
H2 H 0.5865 0.6268 0.4063 0.068 Uiso 1 1 calc R A .
C3 C 0.6343(4) 0.6584(3) 0.2093(3) 0.0662(10) Uani 1 1 d . A .
H3A H 0.5456 0.7086 0.2071 0.079 Uiso 1 1 calc R . .
H3B H 0.6200 0.5754 0.1805 0.079 Uiso 1 1 calc R . .
C3A C 0.7647(3) 0.7347(3) 0.1257(3) 0.0552(8) Uani 1 1 d . . .
H3A1 H 0.8287 0.6744 0.0816 0.066 Uiso 1 1 calc R A .
C4 C 0.7248(4) 0.8493(3) 0.0297(3) 0.0657(10) Uani 1 1 d . A .
H4A H 0.7706 0.8407 -0.0557 0.079 Uiso 1 1 calc R . .
H4B H 0.6200 0.8543 0.0316 0.079 Uiso 1 1 calc R . .
N5 N 0.7812(3) 0.9637(3) 0.0720(2) 0.0525(7) Uani 1 1 d . . .
C5A C 0.7921(3) 1.0936(3) 0.0255(3) 0.0527(8) Uani 1 1 d . A .
C6 C 0.7400(3) 1.1663(3) -0.0777(3) 0.0614(9) Uani 1 1 d . . .
H6 H 0.6884 1.1268 -0.1300 0.074 Uiso 1 1 calc R A .
C7 C 0.7682(4) 1.2981(4) -0.0990(3) 0.0711(10) Uani 1 1 d . A .
H7 H 0.7361 1.3485 -0.1680 0.085 Uiso 1 1 calc R . .
C8 C 0.8437(4) 1.3597(3) -0.0203(3) 0.0711(10) Uani 1 1 d . . .
H8 H 0.8576 1.4500 -0.0364 0.085 Uiso 1 1 calc R A .
C9 C 0.8975(3) 1.2887(3) 0.0801(3) 0.0623(9) Uani 1 1 d . A .
H9 H 0.9495 1.3299 0.1310 0.075 Uiso 1 1 calc R . .
C9A C 0.8727(3) 1.1534(3) 0.1046(3) 0.0519(8) Uani 1 1 d . . .
C10 C 0.9121(3) 1.0493(3) 0.1967(3) 0.0512(8) Uani 1 1 d . A .
C10A C 0.8548(3) 0.9354(3) 0.1745(3) 0.0462(7) Uani 1 1 d . A .
C10B C 0.8462(3) 0.7927(3) 0.2223(3) 0.0500(8) Uani 1 1 d . A .
H10B H 0.9434 0.7551 0.2246 0.060 Uiso 1 1 calc R . .
C11 C 0.8254(3) 0.7633(4) 0.4557(3) 0.0652(10) Uani 1 1 d . . .
H11A H 0.8827 0.8436 0.4434 0.078 Uiso 1 1 calc R A .
H11B H 0.8918 0.6903 0.4626 0.078 Uiso 1 1 calc R . .
C12 C 0.7688(4) 0.5175(3) 0.3581(4) 0.0700(10) Uani 1 1 d . A .
C13 C 0.7188(4) 0.7562(3) 0.5769(3) 0.0555(8) Uani 1 1 d . A .
C14 C 0.7203(4) 0.6552(3) 0.6756(3) 0.0667(10) Uani 1 1 d . . .
H14 H 0.7881 0.5888 0.6673 0.080 Uiso 1 1 calc R A .
C15 C 0.6223(5) 0.6510(4) 0.7870(3) 0.0779(11) Uani 1 1 d . A .
H15 H 0.6246 0.5823 0.8528 0.093 Uiso 1 1 calc R . .
C16 C 0.5231(4) 0.7474(5) 0.7994(4) 0.0836(12) Uani 1 1 d . . .
H16 H 0.4565 0.7439 0.8736 0.100 Uiso 1 1 calc R A .
C17 C 0.5201(5) 0.8496(5) 0.7042(4) 0.0925(13) Uani 1 1 d . A .
H17 H 0.4528 0.9161 0.7138 0.111 Uiso 1 1 calc R . .
C18 C 0.6184(4) 0.8537(4) 0.5925(4) 0.0734(11) Uani 1 1 d . . .
H18 H 0.6162 0.9233 0.5275 0.088 Uiso 1 1 calc R A .
C19 C 0.7695(7) 0.2901(5) 0.4399(6) 0.0764(18) Uani 0.812(11) 1 d PD A 1
H19A H 0.8745 0.3027 0.4218 0.092 Uiso 0.812(11) 1 calc PR A 1
H19B H 0.7399 0.2376 0.3803 0.092 Uiso 0.812(11) 1 calc PR A 1
C20 C 0.7256(16) 0.2244(11) 0.5724(7) 0.111(3) Uani 0.812(11) 1 d PD A 1
H20A H 0.7588 0.2758 0.6301 0.167 Uiso 0.812(11) 1 calc PR A 1
H20B H 0.7684 0.1392 0.5825 0.167 Uiso 0.812(11) 1 calc PR A 1
H20C H 0.6212 0.2157 0.5901 0.167 Uiso 0.812(11) 1 calc PR A 1
C19A C 0.795(2) 0.328(2) 0.498(3) 0.0764(18) Uani 0.188(11) 1 d PD A 2
H19C H 0.8211 0.3645 0.5698 0.092 Uiso 0.188(11) 1 calc PR A 2
H19D H 0.8832 0.3124 0.4418 0.092 Uiso 0.188(11) 1 calc PR A 2
C20A C 0.704(8) 0.204(5) 0.541(5) 0.111(3) Uani 0.188(11) 1 d PD A 2
H20D H 0.6375 0.2135 0.6163 0.167 Uiso 0.188(11) 1 calc PR A 2
H20E H 0.7672 0.1316 0.5587 0.167 Uiso 0.188(11) 1 calc PR A 2
H20F H 0.6502 0.1881 0.4752 0.167 Uiso 0.188(11) 1 calc PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C10 1.720(3) . ?
O1 C12 1.201(4) . ?
O2 C12 1.327(4) . ?
O2 C19 1.467(4) . ?
O2 C19A 1.484(10) . ?
N1 C2 1.465(4) . ?
N1 C11 1.468(4) . ?
N1 C10B 1.476(3) . ?
C2 C12 1.508(4) . ?
C2 C3 1.524(4) . ?
C2 H2 0.9800 . ?
C3 C3A 1.542(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3A C4 1.536(4) . ?
C3A C10B 1.563(4) . ?
C3A H3A1 0.9800 . ?
C4 N5 1.456(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N5 C5A 1.361(4) . ?
N5 C10A 1.379(3) . ?
C5A C6 1.395(4) . ?
C5A C9A 1.422(4) . ?
C6 C7 1.368(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.399(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(4) . ?
C8 H8 0.9300 . ?
C9 C9A 1.399(4) . ?
C9 H9 0.9300 . ?
C9A C10 1.437(4) . ?
C10 C10A 1.363(4) . ?
C10A C10B 1.487(4) . ?
C10B H10B 0.9800 . ?
C11 C13 1.509(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 C18 1.376(4) . ?
C13 C14 1.379(4) . ?
C14 C15 1.388(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.357(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.488(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19A C20A 1.518(10) . ?
C19A H19C 0.9700 . ?
C19A H19D 0.9700 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 C19 117.2(3) . . ?
C12 O2 C19A 111.2(10) . . ?
C19 O2 C19A 33.4(11) . . ?
C2 N1 C11 115.6(2) . . ?
C2 N1 C10B 107.5(2) . . ?
C11 N1 C10B 113.9(2) . . ?
N1 C2 C12 113.8(3) . . ?
N1 C2 C3 101.5(2) . . ?
C12 C2 C3 109.6(3) . . ?
N1 C2 H2 110.5 . . ?
C12 C2 H2 110.5 . . ?
C3 C2 H2 110.5 . . ?
C2 C3 C3A 105.2(2) . . ?
C2 C3 H3A 110.7 . . ?
C3A C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C3A C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C4 C3A C3 115.4(3) . . ?
C4 C3A C10B 107.7(2) . . ?
C3 C3A C10B 104.1(2) . . ?
C4 C3A H3A1 109.8 . . ?
C3 C3A H3A1 109.8 . . ?
C10B C3A H3A1 109.8 . . ?
N5 C4 C3A 103.6(2) . . ?
N5 C4 H4A 111.0 . . ?
C3A C4 H4A 111.0 . . ?
N5 C4 H4B 111.0 . . ?
C3A C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C5A N5 C10A 110.8(2) . . ?
C5A N5 C4 134.4(3) . . ?
C10A N5 C4 114.3(3) . . ?
N5 C5A C6 131.5(3) . . ?
N5 C5A C9A 106.9(3) . . ?
C6 C5A C9A 121.6(3) . . ?
C7 C6 C5A 117.2(3) . . ?
C7 C6 H6 121.4 . . ?
C5A C6 H6 121.4 . . ?
C6 C7 C8 122.3(3) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C9A 118.7(3) . . ?
C8 C9 H9 120.6 . . ?
C9A C9 H9 120.6 . . ?
C9 C9A C5A 119.2(3) . . ?
C9 C9A C10 134.7(3) . . ?
C5A C9A C10 106.1(3) . . ?
C10A C10 C9A 108.1(3) . . ?
C10A C10 Cl1 127.5(3) . . ?
C9A C10 Cl1 124.3(2) . . ?
C10 C10A N5 108.0(3) . . ?
C10 C10A C10B 141.5(3) . . ?
N5 C10A C10B 110.5(2) . . ?
N1 C10B C10A 113.5(2) . . ?
N1 C10B C3A 104.5(2) . . ?
C10A C10B C3A 103.6(2) . . ?
N1 C10B H10B 111.6 . . ?
C10A C10B H10B 111.6 . . ?
C3A C10B H10B 111.6 . . ?
N1 C11 C13 111.7(3) . . ?
N1 C11 H11A 109.3 . . ?
C13 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C13 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
O1 C12 O2 121.3(3) . . ?
O1 C12 C2 126.9(3) . . ?
O2 C12 C2 111.8(3) . . ?
C18 C13 C14 118.1(3) . . ?
C18 C13 C11 120.0(3) . . ?
C14 C13 C11 121.8(3) . . ?
C13 C14 C15 121.0(4) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.6(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 119.6(4) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C13 C18 C17 120.9(4) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
O2 C19 C20 106.5(7) . . ?
O2 C19 H19A 110.4 . . ?
C20 C19 H19A 110.4 . . ?
O2 C19 H19B 110.4 . . ?
C20 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
O2 C19A C20A 103(3) . . ?
O2 C19A H19C 111.2 . . ?
C20A C19A H19C 111.2 . . ?
O2 C19A H19D 111.2 . . ?
C20A C19A H19D 111.2 . . ?
H19C C19A H19D 109.1 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C2 C12 -53.1(4) . . . . ?
C10B N1 C2 C12 75.4(3) . . . . ?
C11 N1 C2 C3 -170.7(3) . . . . ?
C10B N1 C2 C3 -42.2(3) . . . . ?
N1 C2 C3 C3A 36.7(3) . . . . ?
C12 C2 C3 C3A -84.0(3) . . . . ?
C2 C3 C3A C4 -136.5(3) . . . . ?
C2 C3 C3A C10B -18.7(3) . . . . ?
C3 C3A C4 N5 115.6(3) . . . . ?
C10B C3A C4 N5 -0.1(3) . . . . ?
C3A C4 N5 C5A 174.5(3) . . . . ?
C3A C4 N5 C10A 3.0(3) . . . . ?
C10A N5 C5A C6 177.9(3) . . . . ?
C4 N5 C5A C6 6.2(6) . . . . ?
C10A N5 C5A C9A -2.0(3) . . . . ?
C4 N5 C5A C9A -173.8(3) . . . . ?
N5 C5A C6 C7 179.2(3) . . . . ?
C9A C5A C6 C7 -0.8(5) . . . . ?
C5A C6 C7 C8 -1.1(5) . . . . ?
C6 C7 C8 C9 2.2(5) . . . . ?
C7 C8 C9 C9A -1.5(5) . . . . ?
C8 C9 C9A C5A -0.4(5) . . . . ?
C8 C9 C9A C10 178.9(3) . . . . ?
N5 C5A C9A C9 -178.5(3) . . . . ?
C6 C5A C9A C9 1.5(5) . . . . ?
N5 C5A C9A C10 2.0(3) . . . . ?
C6 C5A C9A C10 -177.9(3) . . . . ?
C9 C9A C10 C10A 179.3(3) . . . . ?
C5A C9A C10 C10A -1.3(3) . . . . ?
C9 C9A C10 Cl1 -4.8(5) . . . . ?
C5A C9A C10 Cl1 174.5(2) . . . . ?
C9A C10 C10A N5 0.1(3) . . . . ?
Cl1 C10 C10A N5 -175.5(2) . . . . ?
C9A C10 C10A C10B 179.4(3) . . . . ?
Cl1 C10 C10A C10B 3.7(6) . . . . ?
C5A N5 C10A C10 1.2(4) . . . . ?
C4 N5 C10A C10 174.7(3) . . . . ?
C5A N5 C10A C10B -178.3(2) . . . . ?
C4 N5 C10A C10B -4.8(3) . . . . ?
C2 N1 C10B C10A 142.8(2) . . . . ?
C11 N1 C10B C10A -87.8(3) . . . . ?
C2 N1 C10B C3A 30.6(3) . . . . ?
C11 N1 C10B C3A 160.0(3) . . . . ?
C10 C10A C10B N1 72.2(5) . . . . ?
N5 C10A C10B N1 -108.6(3) . . . . ?
C10 C10A C10B C3A -175.0(4) . . . . ?
N5 C10A C10B C3A 4.2(3) . . . . ?
C4 C3A C10B N1 116.7(3) . . . . ?
C3 C3A C10B N1 -6.3(3) . . . . ?
C4 C3A C10B C10A -2.4(3) . . . . ?
C3 C3A C10B C10A -125.3(3) . . . . ?
C2 N1 C11 C13 -66.3(4) . . . . ?
C10B N1 C11 C13 168.4(3) . . . . ?
C19 O2 C12 O1 -7.4(7) . . . . ?
C19A O2 C12 O1 28.8(15) . . . . ?
C19 O2 C12 C2 172.7(4) . . . . ?
C19A O2 C12 C2 -151.1(15) . . . . ?
N1 C2 C12 O1 -39.0(6) . . . . ?
C3 C2 C12 O1 73.9(5) . . . . ?
N1 C2 C12 O2 140.8(3) . . . . ?
C3 C2 C12 O2 -106.3(3) . . . . ?
N1 C11 C13 C18 -62.5(4) . . . . ?
N1 C11 C13 C14 118.9(3) . . . . ?
C18 C13 C14 C15 0.7(5) . . . . ?
C11 C13 C14 C15 179.3(3) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?
C14 C15 C16 C17 -0.9(6) . . . . ?
C15 C16 C17 C18 1.0(6) . . . . ?
C14 C13 C18 C17 -0.7(5) . . . . ?
C11 C13 C18 C17 -179.3(3) . . . . ?
C16 C17 C18 C13 -0.1(6) . . . . ?
C12 O2 C19 C20 143.6(6) . . . . ?
C19A O2 C19 C20 56(2) . . . . ?
C12 O2 C19A C20A -164(3) . . . . ?
C19 O2 C19A C20A -56(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_iaiq4
_database_code_depnum_ccdc_archive 'CCDC 1018001'
_audit_update_record             
;
2014-08-05 deposited with the CCDC.
2015-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(5aS,12bS)-12-chloro-2,3-dimethoxy-4b,5,5a,12b,14,
15-hexahydro-6H-benzo[5',6']pyrrolizino[2',1':4,5]pyrrolo[2,1-a]isoquinoline
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 Cl N2 O2'
_chemical_formula_sum            'C23 H23 Cl N2 O2'
_chemical_formula_weight         394.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P

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

_cell_length_a                   13.9521(10)
_cell_length_b                   6.6102(4)
_cell_length_c                   21.9770(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.352(7)
_cell_angle_gamma                90.00
_cell_volume                     1944.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2158
_cell_measurement_theta_min      4.1700
_cell_measurement_theta_max      27.9080

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Crys Alis RED'

_exptl_special_details           
;
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7404
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.63
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3804
_reflns_number_gt                2803
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'

_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)+(0.0473P)²+0.4014P] 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         3804
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.14470(14) 0.3357(3) 0.16466(9) 0.0354(5) Uani 1 1 d . . .
H1 H 0.1223 0.4519 0.1802 0.042 Uiso 1 1 calc R . .
C2 C 0.07665(14) 0.1947(3) 0.13355(9) 0.0362(5) Uani 1 1 d . . .
C3 C 0.10952(14) 0.0197(3) 0.10915(9) 0.0370(5) Uani 1 1 d . . .
C4 C 0.21061(14) -0.0079(3) 0.11831(9) 0.0347(5) Uani 1 1 d . . .
H4 H 0.2329 -0.1242 0.1027 0.042 Uiso 1 1 calc R . .
C4A C 0.28024(13) 0.1353(3) 0.15055(9) 0.0302(4) Uani 1 1 d . . .
C4B C 0.39034(13) 0.1028(3) 0.16093(10) 0.0333(4) Uani 1 1 d . . .
H4B H 0.4164 0.0276 0.2006 0.040 Uiso 1 1 calc R . .
C5 C 0.42462(15) -0.0035(3) 0.10901(11) 0.0431(5) Uani 1 1 d . . .
H5A H 0.3826 0.0330 0.0673 0.052 Uiso 1 1 calc R . .
H5B H 0.4236 -0.1493 0.1138 0.052 Uiso 1 1 calc R . .
C5A C 0.53208(14) 0.0744(3) 0.11929(10) 0.0375(5) Uani 1 1 d . . .
H5A1 H 0.5799 -0.0354 0.1350 0.045 Uiso 1 1 calc R . .
C6 C 0.55374(16) 0.1765(3) 0.06174(10) 0.0441(5) Uani 1 1 d . . .
H6A H 0.5949 0.0908 0.0435 0.053 Uiso 1 1 calc R . .
H6B H 0.4923 0.2082 0.0294 0.053 Uiso 1 1 calc R . .
N7 N 0.60664(12) 0.3592(2) 0.08832(8) 0.0385(4) Uani 1 1 d . . .
C7A C 0.66465(14) 0.4990(3) 0.06902(10) 0.0371(5) Uani 1 1 d . . .
C8 C 0.69221(17) 0.5144(4) 0.01289(11) 0.0496(6) Uani 1 1 d . . .
H8 H 0.6684 0.4235 -0.0202 0.060 Uiso 1 1 calc R . .
C9 C 0.75567(17) 0.6682(4) 0.00832(12) 0.0536(6) Uani 1 1 d . . .
H9 H 0.7757 0.6809 -0.0285 0.064 Uiso 1 1 calc R . .
C10 C 0.79103(17) 0.8064(3) 0.05770(12) 0.0521(6) Uani 1 1 d . . .
H10 H 0.8339 0.9092 0.0530 0.063 Uiso 1 1 calc R . .
C11 C 0.76384(15) 0.7936(3) 0.11288(11) 0.0442(5) Uani 1 1 d . . .
H11 H 0.7875 0.8869 0.1453 0.053 Uiso 1 1 calc R . .
C11A C 0.69962(14) 0.6371(3) 0.11951(10) 0.0343(5) Uani 1 1 d . . .
C12 C 0.65908(13) 0.5716(3) 0.16890(9) 0.0329(4) Uani 1 1 d . . .
C12A C 0.60353(14) 0.4025(3) 0.14871(9) 0.0330(4) Uani 1 1 d . . .
C12B C 0.54557(13) 0.2426(3) 0.17070(9) 0.0337(4) Uani 1 1 d . . .
H12B H 0.5814 0.1923 0.2129 0.040 Uiso 1 1 calc R . .
N13 N 0.44217(11) 0.2974(2) 0.16690(7) 0.0318(4) Uani 1 1 d . . .
C14 C 0.42848(15) 0.4118(3) 0.22068(10) 0.0407(5) Uani 1 1 d . . .
H14A H 0.4705 0.5313 0.2278 0.049 Uiso 1 1 calc R . .
H14B H 0.4470 0.3294 0.2587 0.049 Uiso 1 1 calc R . .
C15 C 0.31935(14) 0.4731(3) 0.20593(10) 0.0435(5) Uani 1 1 d . . .
H15A H 0.3050 0.5100 0.2452 0.052 Uiso 1 1 calc R . .
H15B H 0.3083 0.5918 0.1789 0.052 Uiso 1 1 calc R . .
C15A C 0.24757(14) 0.3091(3) 0.17363(9) 0.0313(4) Uani 1 1 d . . .
O16 O -0.02467(10) 0.2069(2) 0.12336(8) 0.0525(4) Uani 1 1 d . . .
O17 O 0.03653(11) -0.1104(2) 0.07784(8) 0.0567(5) Uani 1 1 d . . .
Cl18 Cl 0.68075(4) 0.68561(8) 0.24183(3) 0.04911(18) Uani 1 1 d . . .
C19 C -0.06302(17) 0.3842(4) 0.14448(13) 0.0590(7) Uani 1 1 d . . .
H19A H -0.0368 0.3953 0.1897 0.089 Uiso 1 1 calc R . .
H19B H -0.1346 0.3764 0.1333 0.089 Uiso 1 1 calc R . .
H19C H -0.0436 0.5006 0.1247 0.089 Uiso 1 1 calc R . .
C20 C 0.06182(18) -0.2598(4) 0.03888(12) 0.0557(6) Uani 1 1 d . . .
H20A H 0.0933 -0.1967 0.0101 0.084 Uiso 1 1 calc R . .
H20B H 0.0024 -0.3284 0.0152 0.084 Uiso 1 1 calc R . .
H20C H 0.1070 -0.3555 0.0649 0.084 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
C1 C2 1.368(3) . ?
C1 C15A 1.404(3) . ?
C1 H1 0.9300 . ?
C2 O16 1.370(2) . ?
C2 C3 1.405(3) . ?
C3 O17 1.362(2) . ?
C3 C4 1.380(3) . ?
C4 C4A 1.398(3) . ?
C4 H4 0.9300 . ?
C4A C15A 1.384(3) . ?
C4A C4B 1.504(2) . ?
C4B N13 1.463(2) . ?
C4B C5 1.527(3) . ?
C4B H4B 0.9800 . ?
C5 C5A 1.541(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5A C6 1.537(3) . ?
C5A C12B 1.559(3) . ?
C5A H5A1 0.9800 . ?
C6 N7 1.450(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N7 C12A 1.370(2) . ?
N7 C7A 1.372(2) . ?
C7A C8 1.396(3) . ?
C7A C11A 1.413(3) . ?
C8 C9 1.370(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.398(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(3) . ?
C10 H10 0.9300 . ?
C11 C11A 1.403(3) . ?
C11 H11 0.9300 . ?
C11A C12 1.425(3) . ?
C12 C12A 1.362(3) . ?
C12 Cl18 1.719(2) . ?
C12A C12B 1.491(3) . ?
C12B N13 1.467(2) . ?
C12B H12B 0.9800 . ?
N13 C14 1.461(2) . ?
C14 C15 1.520(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C15A 1.510(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O16 C19 1.420(3) . ?
O17 C20 1.415(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C15A 121.53(17) . . ?
C2 C1 H1 119.2 . . ?
C15A C1 H1 119.2 . . ?
C1 C2 O16 125.49(18) . . ?
C1 C2 C3 119.76(17) . . ?
O16 C2 C3 114.75(18) . . ?
O17 C3 C4 125.33(18) . . ?
O17 C3 C2 115.76(17) . . ?
C4 C3 C2 118.91(18) . . ?
C3 C4 C4A 121.36(18) . . ?
C3 C4 H4 119.3 . . ?
C4A C4 H4 119.3 . . ?
C15A C4A C4 119.62(17) . . ?
C15A C4A C4B 119.39(17) . . ?
C4 C4A C4B 120.98(16) . . ?
N13 C4B C4A 110.25(15) . . ?
N13 C4B C5 102.75(15) . . ?
C4A C4B C5 118.28(17) . . ?
N13 C4B H4B 108.4 . . ?
C4A C4B H4B 108.4 . . ?
C5 C4B H4B 108.4 . . ?
C4B C5 C5A 103.48(16) . . ?
C4B C5 H5A 111.1 . . ?
C5A C5 H5A 111.1 . . ?
C4B C5 H5B 111.1 . . ?
C5A C5 H5B 111.1 . . ?
H5A C5 H5B 109.0 . . ?
C6 C5A C5 115.77(18) . . ?
C6 C5A C12B 105.74(15) . . ?
C5 C5A C12B 105.00(15) . . ?
C6 C5A H5A1 110.0 . . ?
C5 C5A H5A1 110.0 . . ?
C12B C5A H5A1 110.0 . . ?
N7 C6 C5A 103.31(16) . . ?
N7 C6 H6A 111.1 . . ?
C5A C6 H6A 111.1 . . ?
N7 C6 H6B 111.1 . . ?
C5A C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
C12A N7 C7A 109.95(16) . . ?
C12A N7 C6 114.38(16) . . ?
C7A N7 C6 135.58(17) . . ?
N7 C7A C8 131.0(2) . . ?
N7 C7A C11A 107.20(17) . . ?
C8 C7A C11A 121.78(19) . . ?
C9 C8 C7A 117.6(2) . . ?
C9 C8 H8 121.2 . . ?
C7A C8 H8 121.2 . . ?
C8 C9 C10 121.5(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 121.4(2) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C11A 118.8(2) . . ?
C10 C11 H11 120.6 . . ?
C11A C11 H11 120.6 . . ?
C11 C11A C7A 118.96(19) . . ?
C11 C11A C12 134.8(2) . . ?
C7A C11A C12 106.17(16) . . ?
C12A C12 C11A 108.21(17) . . ?
C12A C12 Cl18 126.75(15) . . ?
C11A C12 Cl18 125.01(15) . . ?
C12 C12A N7 108.46(17) . . ?
C12 C12A C12B 141.90(18) . . ?
N7 C12A C12B 109.52(16) . . ?
N13 C12B C12A 114.91(15) . . ?
N13 C12B C5A 102.63(14) . . ?
C12A C12B C5A 103.68(15) . . ?
N13 C12B H12B 111.7 . . ?
C12A C12B H12B 111.7 . . ?
C5A C12B H12B 111.7 . . ?
C14 N13 C4B 110.73(15) . . ?
C14 N13 C12B 115.62(15) . . ?
C4B N13 C12B 103.98(14) . . ?
N13 C14 C15 108.47(16) . . ?
N13 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
N13 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C15A C15 C14 113.64(16) . . ?
C15A C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C15A C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C4A C15A C1 118.81(17) . . ?
C4A C15A C15 121.66(17) . . ?
C1 C15A C15 119.50(17) . . ?
C2 O16 C19 117.49(17) . . ?
C3 O17 C20 117.89(16) . . ?
O16 C19 H19A 109.5 . . ?
O16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O17 C20 H20A 109.5 . . ?
O17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15A C1 C2 O16 179.13(18) . . . . ?
C15A C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 O17 -178.77(18) . . . . ?
O16 C2 C3 O17 1.3(3) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
O16 C2 C3 C4 -178.63(17) . . . . ?
O17 C3 C4 C4A 179.29(19) . . . . ?
C2 C3 C4 C4A -0.8(3) . . . . ?
C3 C4 C4A C15A -0.3(3) . . . . ?
C3 C4 C4A C4B 179.32(18) . . . . ?
C15A C4A C4B N13 -27.2(2) . . . . ?
C4 C4A C4B N13 153.19(17) . . . . ?
C15A C4A C4B C5 -144.95(18) . . . . ?
C4 C4A C4B C5 35.4(3) . . . . ?
N13 C4B C5 C5A 33.13(19) . . . . ?
C4A C4B C5 C5A 154.77(17) . . . . ?
C4B C5 C5A C6 -123.78(18) . . . . ?
C4B C5 C5A C12B -7.6(2) . . . . ?
C5 C5A C6 N7 133.34(17) . . . . ?
C12B C5A C6 N7 17.58(19) . . . . ?
C5A C6 N7 C12A -11.8(2) . . . . ?
C5A C6 N7 C7A 164.3(2) . . . . ?
C12A N7 C7A C8 177.8(2) . . . . ?
C6 N7 C7A C8 1.5(4) . . . . ?
C12A N7 C7A C11A -0.1(2) . . . . ?
C6 N7 C7A C11A -176.4(2) . . . . ?
N7 C7A C8 C9 -177.0(2) . . . . ?
C11A C7A C8 C9 0.6(3) . . . . ?
C7A C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C11A 0.4(3) . . . . ?
C10 C11 C11A C7A -0.4(3) . . . . ?
C10 C11 C11A C12 177.2(2) . . . . ?
N7 C7A C11A C11 178.05(17) . . . . ?
C8 C7A C11A C11 -0.1(3) . . . . ?
N7 C7A C11A C12 -0.2(2) . . . . ?
C8 C7A C11A C12 -178.30(18) . . . . ?
C11 C11A C12 C12A -177.4(2) . . . . ?
C7A C11A C12 C12A 0.4(2) . . . . ?
C11 C11A C12 Cl18 0.9(3) . . . . ?
C7A C11A C12 Cl18 178.74(14) . . . . ?
C11A C12 C12A N7 -0.5(2) . . . . ?
Cl18 C12 C12A N7 -178.78(14) . . . . ?
C11A C12 C12A C12B 174.8(2) . . . . ?
Cl18 C12 C12A C12B -3.5(4) . . . . ?
C7A N7 C12A C12 0.4(2) . . . . ?
C6 N7 C12A C12 177.51(16) . . . . ?
C7A N7 C12A C12B -176.52(16) . . . . ?
C6 N7 C12A C12B 0.6(2) . . . . ?
C12 C12A C12B N13 84.4(3) . . . . ?
N7 C12A C12B N13 -100.42(19) . . . . ?
C12 C12A C12B C5A -164.5(2) . . . . ?
N7 C12A C12B C5A 10.8(2) . . . . ?
C6 C5A C12B N13 102.52(16) . . . . ?
C5 C5A C12B N13 -20.4(2) . . . . ?
C6 C5A C12B C12A -17.40(19) . . . . ?
C5 C5A C12B C12A -140.30(16) . . . . ?
C4A C4B N13 C14 60.3(2) . . . . ?
C5 C4B N13 C14 -172.72(16) . . . . ?
C4A C4B N13 C12B -174.89(15) . . . . ?
C5 C4B N13 C12B -47.93(18) . . . . ?
C12A C12B N13 C14 -84.4(2) . . . . ?
C5A C12B N13 C14 163.85(16) . . . . ?
C12A C12B N13 C4B 154.04(16) . . . . ?
C5A C12B N13 C4B 42.25(18) . . . . ?
C4B N13 C14 C15 -67.7(2) . . . . ?
C12B N13 C14 C15 174.45(16) . . . . ?
N13 C14 C15 C15A 40.7(2) . . . . ?
C4 C4A C15A C1 0.8(3) . . . . ?
C4B C4A C15A C1 -178.80(16) . . . . ?
C4 C4A C15A C15 -176.95(18) . . . . ?
C4B C4A C15A C15 3.4(3) . . . . ?
C2 C1 C15A C4A -0.3(3) . . . . ?
C2 C1 C15A C15 177.53(18) . . . . ?
C14 C15 C15A C4A -10.4(3) . . . . ?
C14 C15 C15A C1 171.87(17) . . . . ?
C1 C2 O16 C19 2.7(3) . . . . ?
C3 C2 O16 C19 -177.37(19) . . . . ?
C4 C3 O17 C20 -15.9(3) . . . . ?
C2 C3 O17 C20 164.14(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.052
