# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H27 N O4'
_chemical_formula_weight         333.42

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.131(2)
_cell_length_b                   15.863(4)
_cell_length_c                   14.367(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.185(3)
_cell_angle_gamma                90.00
_cell_volume                     1823.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    3125
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.17
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9833
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            9585
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         27.45
_reflns_number_total             4039
_reflns_number_gt                2887
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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)+(0.0682P)²+0.2977P] 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         4039
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 -0.05704(19) 0.18404(10) 0.72714(10) 0.0219(3) Uani 1 1 d . . .
C2 C 0.12356(19) 0.16420(10) 0.77259(10) 0.0210(3) Uani 1 1 d . . .
H2 H 0.2007 0.1966 0.7389 0.025 Uiso 1 1 calc R . .
C3 C 0.13342(19) 0.06791(10) 0.74725(10) 0.0221(3) Uani 1 1 d . . .
C4 C -0.04618(19) 0.03390(10) 0.74117(11) 0.0245(4) Uani 1 1 d . . .
H4A H -0.0702 -0.0116 0.6935 0.029 Uiso 1 1 calc R . .
H4B H -0.0648 0.0124 0.8032 0.029 Uiso 1 1 calc R . .
C5 C -0.1513(2) 0.11088(10) 0.71164(10) 0.0232(3) Uani 1 1 d . . .
C6 C -0.3202(2) 0.11444(11) 0.67248(11) 0.0272(4) Uani 1 1 d . . .
H6 H -0.3850 0.0644 0.6630 0.033 Uiso 1 1 calc R . .
C7 C -0.3924(2) 0.19215(12) 0.64755(11) 0.0316(4) Uani 1 1 d . . .
H7 H -0.5077 0.1955 0.6208 0.038 Uiso 1 1 calc R . .
C8 C -0.2978(2) 0.26466(12) 0.66137(11) 0.0304(4) Uani 1 1 d . . .
H8 H -0.3484 0.3175 0.6431 0.036 Uiso 1 1 calc R . .
C9 C -0.1296(2) 0.26158(11) 0.70165(11) 0.0263(4) Uani 1 1 d . . .
H9 H -0.0653 0.3118 0.7116 0.032 Uiso 1 1 calc R . .
C10 C 0.2623(2) 0.02201(10) 0.81859(11) 0.0242(3) Uani 1 1 d . . .
C11 C 0.5537(2) 0.00238(14) 0.86576(13) 0.0393(5) Uani 1 1 d . . .
H11A H 0.5481 0.0174 0.9313 0.059 Uiso 1 1 calc R . .
H11B H 0.6591 0.0228 0.8499 0.059 Uiso 1 1 calc R . .
H11C H 0.5478 -0.0590 0.8586 0.059 Uiso 1 1 calc R . .
C12 C 0.18403(19) 0.05904(10) 0.64988(11) 0.0229(3) Uani 1 1 d . . .
C13 C 0.2380(3) -0.03990(12) 0.53638(12) 0.0368(4) Uani 1 1 d . . .
H13A H 0.1623 -0.0106 0.4861 0.055 Uiso 1 1 calc R . .
H13B H 0.2323 -0.1007 0.5243 0.055 Uiso 1 1 calc R . .
H13C H 0.3525 -0.0201 0.5378 0.055 Uiso 1 1 calc R . .
C14 C 0.0412(2) 0.16496(11) 0.93328(11) 0.0259(4) Uani 1 1 d . . .
H14 H -0.0386 0.1227 0.8990 0.031 Uiso 1 1 calc R . .
C15 C 0.1198(2) 0.12466(13) 1.02747(12) 0.0371(5) Uani 1 1 d . . .
H15A H 0.1809 0.0737 1.0154 0.056 Uiso 1 1 calc R . .
H15B H 0.0317 0.1097 1.0631 0.056 Uiso 1 1 calc R . .
H15C H 0.1970 0.1647 1.0642 0.056 Uiso 1 1 calc R . .
C16 C -0.0627(2) 0.24183(12) 0.95132(12) 0.0332(4) Uani 1 1 d . . .
H16A H 0.0100 0.2836 0.9884 0.050 Uiso 1 1 calc R . .
H16B H -0.1499 0.2244 0.9864 0.050 Uiso 1 1 calc R . .
H16C H -0.1145 0.2667 0.8908 0.050 Uiso 1 1 calc R . .
C17 C 0.2852(2) 0.25028(11) 0.90359(11) 0.0281(4) Uani 1 1 d . . .
H17 H 0.2834 0.2602 0.9721 0.034 Uiso 1 1 calc R . .
C18 C 0.4643(2) 0.22626(13) 0.89697(14) 0.0378(5) Uani 1 1 d . . .
H18A H 0.4980 0.1770 0.9369 0.057 Uiso 1 1 calc R . .
H18B H 0.5389 0.2736 0.9185 0.057 Uiso 1 1 calc R . .
H18C H 0.4713 0.2128 0.8312 0.057 Uiso 1 1 calc R . .
C19 C 0.2377(3) 0.33371(12) 0.85353(14) 0.0388(5) Uani 1 1 d . . .
H19A H 0.2448 0.3282 0.7864 0.058 Uiso 1 1 calc R . .
H19B H 0.3146 0.3779 0.8822 0.058 Uiso 1 1 calc R . .
H19C H 0.1233 0.3487 0.8598 0.058 Uiso 1 1 calc R . .
N1 N 0.16940(16) 0.18012(8) 0.87435(9) 0.0228(3) Uani 1 1 d . . .
O1 O 0.23323(15) -0.02473(8) 0.87958(8) 0.0318(3) Uani 1 1 d . . .
O2 O 0.41512(14) 0.04067(8) 0.80297(8) 0.0301(3) Uani 1 1 d . . .
O3 O 0.21437(15) 0.11526(8) 0.60002(8) 0.0301(3) Uani 1 1 d . . .
O4 O 0.18880(16) -0.02260(7) 0.62648(8) 0.0324(3) 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 C9 1.385(2) . ?
C1 C5 1.387(2) . ?
C1 C2 1.531(2) . ?
C2 N1 1.4655(19) . ?
C2 C3 1.576(2) . ?
C2 H2 1.0000 . ?
C3 C10 1.516(2) . ?
C3 C12 1.533(2) . ?
C3 C4 1.545(2) . ?
C4 C5 1.508(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.390(2) . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 O1 1.2028(19) . ?
C10 O2 1.334(2) . ?
C11 O2 1.447(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O3 1.1967(19) . ?
C12 O4 1.340(2) . ?
C13 O4 1.4469(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N1 1.474(2) . ?
C14 C15 1.531(2) . ?
C14 C16 1.531(2) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N1 1.470(2) . ?
C17 C19 1.523(3) . ?
C17 C18 1.525(2) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C9 C1 C5 120.22(15) . . ?
C9 C1 C2 128.82(14) . . ?
C5 C1 C2 110.96(14) . . ?
N1 C2 C1 116.48(12) . . ?
N1 C2 C3 112.53(12) . . ?
C1 C2 C3 100.65(12) . . ?
N1 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C10 C3 C12 107.93(13) . . ?
C10 C3 C4 113.83(13) . . ?
C12 C3 C4 108.66(13) . . ?
C10 C3 C2 111.51(12) . . ?
C12 C3 C2 109.43(12) . . ?
C4 C3 C2 105.40(12) . . ?
C5 C4 C3 102.49(13) . . ?
C5 C4 H4A 111.3 . . ?
C3 C4 H4A 111.3 . . ?
C5 C4 H4B 111.3 . . ?
C3 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
C1 C5 C6 120.62(15) . . ?
C1 C5 C4 111.28(14) . . ?
C6 C5 C4 128.10(15) . . ?
C7 C6 C5 118.96(16) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C6 120.34(16) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.94(17) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C1 C9 C8 118.91(16) . . ?
C1 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
O1 C10 O2 124.61(15) . . ?
O1 C10 C3 125.95(15) . . ?
O2 C10 C3 109.44(13) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 123.50(14) . . ?
O3 C12 C3 126.50(15) . . ?
O4 C12 C3 110.00(13) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 110.41(14) . . ?
N1 C14 C16 115.75(14) . . ?
C15 C14 C16 109.84(14) . . ?
N1 C14 H14 106.8 . . ?
C15 C14 H14 106.8 . . ?
C16 C14 H14 106.8 . . ?
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 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C19 115.27(14) . . ?
N1 C17 C18 111.32(14) . . ?
C19 C17 C18 110.65(15) . . ?
N1 C17 H17 106.3 . . ?
C19 C17 H17 106.3 . . ?
C18 C17 H17 106.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 N1 C17 116.91(12) . . ?
C2 N1 C14 117.63(12) . . ?
C17 N1 C14 116.20(12) . . ?
C10 O2 C11 116.61(13) . . ?
C12 O4 C13 115.62(13) . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 980641'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxla

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H27 N O4'
_chemical_formula_weight         429.50

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pnn2 '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   14.9740(15)
_cell_length_b                   19.497(2)
_cell_length_c                   7.6466(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2232.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    5039
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.33
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9831
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            12301
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         27.55
_reflns_number_total             4878
_reflns_number_gt                4417
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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)+(0.0387P)²+0.4624P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(8)
_refine_ls_number_reflns         4878
_refine_ls_number_parameters     291
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
C1 C 0.32851(10) 0.36187(7) 0.7551(2) 0.0169(3) Uani 1 1 d . . .
H1 H 0.3701 0.3989 0.7942 0.020 Uiso 1 1 calc R . .
C2 C 0.32282(10) 0.36258(7) 0.54973(19) 0.0175(3) Uani 1 1 d . . .
C3 C 0.22328(10) 0.34940(8) 0.5050(2) 0.0204(3) Uani 1 1 d . . .
H3A H 0.2045 0.3768 0.4023 0.025 Uiso 1 1 calc R . .
H3B H 0.2125 0.3002 0.4807 0.025 Uiso 1 1 calc R . .
C4 C 0.17471(10) 0.37198(7) 0.6674(2) 0.0192(3) Uani 1 1 d . . .
C5 C 0.08347(11) 0.38223(8) 0.6892(2) 0.0236(3) Uani 1 1 d . . .
H5 H 0.0435 0.3763 0.5940 0.028 Uiso 1 1 calc R . .
C6 C 0.05195(11) 0.40132(8) 0.8531(2) 0.0279(4) Uani 1 1 d . . .
H6 H -0.0103 0.4082 0.8702 0.033 Uiso 1 1 calc R . .
C7 C 0.11026(11) 0.41048(8) 0.9919(2) 0.0280(4) Uani 1 1 d . . .
H7 H 0.0875 0.4232 1.1032 0.034 Uiso 1 1 calc R . .
C8 C 0.20208(11) 0.40118(8) 0.9703(2) 0.0241(3) Uani 1 1 d . . .
H8 H 0.2421 0.4084 1.0650 0.029 Uiso 1 1 calc R . .
C9 C 0.23362(10) 0.38109(7) 0.8067(2) 0.0187(3) Uani 1 1 d . . .
C10 C 0.40711(10) 0.30518(8) 0.9928(2) 0.0206(3) Uani 1 1 d . . .
H10A H 0.4121 0.2605 1.0536 0.025 Uiso 1 1 calc R . .
H10B H 0.3712 0.3361 1.0675 0.025 Uiso 1 1 calc R . .
C11 C 0.49930(10) 0.33520(8) 0.9702(2) 0.0215(3) Uani 1 1 d . . .
C12 C 0.52223(13) 0.39806(10) 1.0383(3) 0.0383(5) Uani 1 1 d . . .
H12 H 0.4783 0.4249 1.0961 0.046 Uiso 1 1 calc R . .
C13 C 0.60938(16) 0.42279(13) 1.0235(3) 0.0546(7) Uani 1 1 d . . .
H13 H 0.6245 0.4661 1.0720 0.065 Uiso 1 1 calc R . .
C14 C 0.67326(13) 0.38470(13) 0.9391(3) 0.0459(6) Uani 1 1 d . . .
H14 H 0.7325 0.4017 0.9287 0.055 Uiso 1 1 calc R . .
C15 C 0.65114(12) 0.32167(11) 0.8693(3) 0.0421(5) Uani 1 1 d . . .
H15 H 0.6951 0.2951 0.8109 0.051 Uiso 1 1 calc R . .
C16 C 0.56455(12) 0.29725(9) 0.8847(3) 0.0316(4) Uani 1 1 d . . .
H16 H 0.5496 0.2539 0.8360 0.038 Uiso 1 1 calc R . .
C17 C 0.28953(10) 0.24259(7) 0.8439(2) 0.0221(3) Uani 1 1 d . . .
H17A H 0.2512 0.2430 0.7384 0.027 Uiso 1 1 calc R . .
H17B H 0.2517 0.2544 0.9457 0.027 Uiso 1 1 calc R . .
C18 C 0.32755(10) 0.17122(8) 0.8689(2) 0.0203(3) Uani 1 1 d . . .
C19 C 0.32128(12) 0.13758(9) 1.0282(2) 0.0294(4) Uani 1 1 d . . .
H19 H 0.2963 0.1608 1.1259 0.035 Uiso 1 1 calc R . .
C20 C 0.35103(12) 0.07015(9) 1.0477(3) 0.0319(4) Uani 1 1 d . . .
H20 H 0.3459 0.0477 1.1576 0.038 Uiso 1 1 calc R . .
C21 C 0.38766(11) 0.03638(8) 0.9075(3) 0.0282(4) Uani 1 1 d . . .
H21 H 0.4070 -0.0098 0.9194 0.034 Uiso 1 1 calc R . .
C22 C 0.39621(13) 0.06975(9) 0.7492(3) 0.0348(4) Uani 1 1 d . . .
H22 H 0.4225 0.0466 0.6527 0.042 Uiso 1 1 calc R . .
C23 C 0.36672(12) 0.13675(8) 0.7298(2) 0.0290(4) Uani 1 1 d . . .
H23 H 0.3734 0.1593 0.6204 0.035 Uiso 1 1 calc R . .
C24 C 0.34873(9) 0.43177(7) 0.4695(2) 0.0189(3) Uani 1 1 d . . .
C25 C 0.39583(14) 0.54551(8) 0.5146(3) 0.0362(5) Uani 1 1 d . . .
H25A H 0.4440 0.5403 0.4288 0.054 Uiso 1 1 calc R . .
H25B H 0.4158 0.5756 0.6095 0.054 Uiso 1 1 calc R . .
H25C H 0.3434 0.5656 0.4577 0.054 Uiso 1 1 calc R . .
C26 C 0.38490(10) 0.30858(7) 0.4721(2) 0.0180(3) Uani 1 1 d . . .
C27 C 0.53675(11) 0.28154(9) 0.4228(3) 0.0289(4) Uani 1 1 d . . .
H27A H 0.5338 0.2399 0.4942 0.043 Uiso 1 1 calc R . .
H27B H 0.5961 0.3023 0.4342 0.043 Uiso 1 1 calc R . .
H27C H 0.5257 0.2699 0.3000 0.043 Uiso 1 1 calc R . .
N1 N 0.36038(8) 0.29505(6) 0.82453(17) 0.0176(3) Uani 1 1 d . . .
O1 O 0.34606(8) 0.44184(6) 0.31400(16) 0.0293(3) Uani 1 1 d . . .
O2 O 0.37266(8) 0.47863(5) 0.58567(16) 0.0279(3) Uani 1 1 d . . .
O3 O 0.36191(7) 0.25452(5) 0.41094(16) 0.0235(2) Uani 1 1 d . . .
O4 O 0.46959(7) 0.32984(5) 0.48207(16) 0.0223(2) 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 N1 1.4857(19) . ?
C1 C9 1.521(2) . ?
C1 C2 1.572(2) . ?
C1 H1 1.0000 . ?
C2 C26 1.525(2) . ?
C2 C24 1.532(2) . ?
C2 C3 1.551(2) . ?
C3 C4 1.505(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.391(2) . ?
C4 C9 1.394(2) . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(2) . ?
C8 H8 0.9500 . ?
C10 N1 1.478(2) . ?
C10 C11 1.509(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.375(2) . ?
C11 C16 1.389(2) . ?
C12 C13 1.396(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N1 1.4812(19) . ?
C17 C18 1.516(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.387(2) . ?
C18 C23 1.388(2) . ?
C19 C20 1.396(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.372(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.381(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 O1 1.206(2) . ?
C24 O2 1.3237(19) . ?
C25 O2 1.4546(19) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 O3 1.2035(18) . ?
C26 O4 1.3363(17) . ?
C27 O4 1.4504(18) . ?
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
N1 C1 C9 115.03(12) . . ?
N1 C1 C2 112.46(12) . . ?
C9 C1 C2 101.90(12) . . ?
N1 C1 H1 109.1 . . ?
C9 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
C26 C2 C24 107.33(12) . . ?
C26 C2 C3 112.69(12) . . ?
C24 C2 C3 107.52(12) . . ?
C26 C2 C1 110.45(12) . . ?
C24 C2 C1 113.20(12) . . ?
C3 C2 C1 105.72(12) . . ?
C4 C3 C2 103.54(12) . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.0 . . ?
C5 C4 C9 120.77(15) . . ?
C5 C4 C3 128.01(15) . . ?
C9 C4 C3 111.21(13) . . ?
C6 C5 C4 118.71(16) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C7 C6 C5 120.74(15) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.86(16) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 118.43(16) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C4 120.48(14) . . ?
C8 C9 C1 128.20(14) . . ?
C4 C9 C1 111.19(14) . . ?
N1 C10 C11 112.65(13) . . ?
N1 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C16 118.52(16) . . ?
C12 C11 C10 122.03(15) . . ?
C16 C11 C10 119.39(15) . . ?
C11 C12 C13 120.69(19) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.77(18) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 119.83(19) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 120.99(18) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N1 C17 C18 112.19(12) . . ?
N1 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
N1 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C23 118.21(15) . . ?
C19 C18 C17 121.33(15) . . ?
C23 C18 C17 120.41(15) . . ?
C18 C19 C20 121.16(16) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 119.75(17) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 119.72(15) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C23 120.53(18) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C18 120.58(17) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
O1 C24 O2 123.94(14) . . ?
O1 C24 C2 122.01(14) . . ?
O2 C24 C2 114.05(13) . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C26 O4 124.42(14) . . ?
O3 C26 C2 125.57(13) . . ?
O4 C26 C2 110.02(12) . . ?
O4 C27 H27A 109.5 . . ?
O4 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O4 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C10 N1 C17 110.15(12) . . ?
C10 N1 C1 110.25(12) . . ?
C17 N1 C1 114.28(11) . . ?
C24 O2 C25 115.64(13) . . ?
C26 O4 C27 116.03(12) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 980642'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18.50 H24 Cl N3 O3'
_chemical_formula_weight         371.86

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           Tetragonal
_symmetry_space_group_name_H-M   'P4(3)2(1)2 '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   10.0579(6)
_cell_length_b                   10.0579(6)
_cell_length_c                   36.133(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3655.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    123
_cell_measurement_reflns_used    9629
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.44
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1576
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9335
_exptl_absorpt_correction_T_max  0.9442
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            20527
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4182
_reflns_number_gt                3942
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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)+(0.0544P)²+1.8792P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_number_reflns         4182
_refine_ls_number_parameters     249
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.098
_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
Cl1 Cl 0.2941(2) 0.8325(4) 0.28243(7) 0.1072(9) Uani 0.50 1 d PU A 1
C19 C 0.1563(15) 0.8437(15) 0.2500 0.145(4) Uani 0.25 1 d PU A 1
H19A H 0.1603 0.9291 0.2365 0.174 Uiso 0.25 1 calc PR A 1
H19B H 0.0709 0.8397 0.2635 0.174 Uiso 0.25 1 calc PR A 1
Cl2 Cl 0.2034(5) 0.8635(4) 0.28265(12) 0.1649(18) Uani 0.50 1 d PDU B 2
C20 C 0.2662(12) 0.7338(12) 0.2500 0.149(4) Uani 0.25 1 d PDU B 2
H20A H 0.2520 0.6413 0.2585 0.178 Uiso 0.25 1 calc PR B 2
H20B H 0.3587 0.7480 0.2415 0.178 Uiso 0.25 1 calc PR B 2
C1 C 0.86255(18) 0.26963(17) 0.19586(5) 0.0171(3) Uani 1 1 d . . .
H1 H 0.8158 0.2954 0.2192 0.020 Uiso 1 1 calc R . .
C2 C 1.00977(18) 0.26718(18) 0.20415(5) 0.0188(3) Uani 1 1 d . . .
C3 C 1.07302(19) 0.19156(19) 0.23113(5) 0.0224(4) Uani 1 1 d . . .
H3 H 1.0234 0.1341 0.2468 0.027 Uiso 1 1 calc R . .
C4 C 1.2105(2) 0.2017(2) 0.23475(5) 0.0264(4) Uani 1 1 d . . .
H4 H 1.2549 0.1499 0.2530 0.032 Uiso 1 1 calc R . .
C5 C 1.28408(19) 0.2862(2) 0.21215(5) 0.0271(4) Uani 1 1 d . . .
H5 H 1.3780 0.2908 0.2147 0.033 Uiso 1 1 calc R . .
C6 C 1.22001(19) 0.3640(2) 0.18580(5) 0.0246(4) Uani 1 1 d . . .
H6 H 1.2689 0.4237 0.1706 0.029 Uiso 1 1 calc R . .
C7 C 1.08276(19) 0.35271(19) 0.18209(5) 0.0209(4) Uani 1 1 d . . .
C8 C 0.99485(18) 0.41848(19) 0.15432(5) 0.0221(4) Uani 1 1 d . . .
H8A H 1.0077 0.3789 0.1295 0.027 Uiso 1 1 calc R . .
H8B H 1.0139 0.5149 0.1529 0.027 Uiso 1 1 calc R . .
C9 C 0.8085(2) 0.51289(18) 0.19101(5) 0.0212(4) Uani 1 1 d . . .
H9A H 0.8652 0.5195 0.2133 0.025 Uiso 1 1 calc R . .
H9B H 0.8217 0.5949 0.1763 0.025 Uiso 1 1 calc R . .
C10 C 0.6641(2) 0.5050(2) 0.20292(5) 0.0260(4) Uani 1 1 d . . .
H10A H 0.6067 0.5066 0.1810 0.039 Uiso 1 1 calc R . .
H10B H 0.6429 0.5811 0.2188 0.039 Uiso 1 1 calc R . .
H10C H 0.6493 0.4223 0.2166 0.039 Uiso 1 1 calc R . .
C11 C 0.76243(19) 0.36872(18) 0.13587(5) 0.0200(4) Uani 1 1 d . . .
H11A H 0.6728 0.3463 0.1453 0.024 Uiso 1 1 calc R . .
H11B H 0.7957 0.2911 0.1218 0.024 Uiso 1 1 calc R . .
C12 C 0.7515(2) 0.48720(19) 0.10991(5) 0.0237(4) Uani 1 1 d . . .
H12A H 0.7088 0.5614 0.1229 0.036 Uiso 1 1 calc R . .
H12B H 0.6980 0.4626 0.0883 0.036 Uiso 1 1 calc R . .
H12C H 0.8405 0.5140 0.1018 0.036 Uiso 1 1 calc R . .
C13 C 0.80172(17) 0.14433(17) 0.18274(5) 0.0174(3) Uani 1 1 d . . .
C14 C 0.68091(17) 0.10332(17) 0.19950(4) 0.0173(3) Uani 1 1 d . . .
C15 C 0.69620(19) -0.10752(18) 0.16457(5) 0.0213(4) Uani 1 1 d . . .
C16 C 0.86395(18) 0.06812(17) 0.15492(5) 0.0181(3) Uani 1 1 d . . .
C17 C 0.51775(19) -0.0761(2) 0.20947(5) 0.0246(4) Uani 1 1 d . . .
H17A H 0.4801 -0.1515 0.1959 0.037 Uiso 1 1 calc R . .
H17B H 0.4504 -0.0062 0.2119 0.037 Uiso 1 1 calc R . .
H17C H 0.5458 -0.1054 0.2341 0.037 Uiso 1 1 calc R . .
C18 C 0.8771(2) -0.1464(2) 0.12147(6) 0.0296(4) Uani 1 1 d . . .
H18A H 0.9381 -0.2046 0.1351 0.044 Uiso 1 1 calc R . .
H18B H 0.9276 -0.0928 0.1037 0.044 Uiso 1 1 calc R . .
H18C H 0.8118 -0.2008 0.1082 0.044 Uiso 1 1 calc R . .
N1 N 0.85366(15) 0.39418(14) 0.16816(4) 0.0175(3) Uani 1 1 d . . .
N2 N 0.63306(15) -0.02378(15) 0.18923(4) 0.0195(3) Uani 1 1 d . . .
N3 N 0.80816(17) -0.05855(15) 0.14749(4) 0.0217(3) Uani 1 1 d . . .
O1 O 0.61517(13) 0.16753(13) 0.22241(3) 0.0213(3) Uani 1 1 d . . .
O2 O 0.65366(15) -0.21899(14) 0.15779(4) 0.0305(3) Uani 1 1 d . . .
O3 O 0.96100(13) 0.10491(14) 0.13625(4) 0.0233(3) 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
Cl1 C19 1.818(13) . ?
C19 Cl1 1.818(13) 8_665 ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
Cl2 C20 1.868(13) . ?
C20 Cl2 1.868(13) 8_665 ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C1 C13 1.479(2) . ?
C1 C2 1.511(2) . ?
C1 N1 1.606(2) . ?
C1 H1 1.0000 . ?
C2 C7 1.384(2) . ?
C2 C3 1.391(3) . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.492(3) . ?
C8 N1 1.525(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.518(3) . ?
C9 N1 1.521(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N1 1.506(2) . ?
C11 C12 1.520(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C16 1.411(2) . ?
C13 C14 1.419(2) . ?
C14 O1 1.241(2) . ?
C14 N2 1.415(2) . ?
C15 O2 1.225(2) . ?
C15 N3 1.375(2) . ?
C15 N2 1.381(2) . ?
C16 O3 1.243(2) . ?
C16 N3 1.418(2) . ?
C17 N2 1.468(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N3 1.465(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
Cl1 C19 Cl1 108.7(11) . 8_665 ?
Cl1 C19 H19A 109.9 . . ?
Cl1 C19 H19A 109.9 8_665 . ?
Cl1 C19 H19B 109.9 . . ?
Cl1 C19 H19B 109.9 8_665 . ?
H19A C19 H19B 108.3 . . ?
Cl2 C20 Cl2 85.8(8) . 8_665 ?
Cl2 C20 H20A 114.3 . . ?
Cl2 C20 H20A 114.3 8_665 . ?
Cl2 C20 H20B 114.3 . . ?
Cl2 C20 H20B 114.3 8_665 . ?
H20A C20 H20B 111.5 . . ?
C13 C1 C2 117.07(15) . . ?
C13 C1 N1 116.22(13) . . ?
C2 C1 N1 101.00(13) . . ?
C13 C1 H1 107.3 . . ?
C2 C1 H1 107.3 . . ?
N1 C1 H1 107.3 . . ?
C7 C2 C3 120.08(17) . . ?
C7 C2 C1 113.30(16) . . ?
C3 C2 C1 126.60(16) . . ?
C2 C3 C4 118.70(18) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.15(18) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 119.94(18) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 118.66(18) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C2 C7 C6 121.45(18) . . ?
C2 C7 C8 110.41(16) . . ?
C6 C7 C8 128.05(17) . . ?
C7 C8 N1 105.08(13) . . ?
C7 C8 H8A 110.7 . . ?
N1 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
N1 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C10 C9 N1 113.50(15) . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
N1 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 112.87(14) . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C13 C14 121.74(15) . . ?
C16 C13 C1 120.53(15) . . ?
C14 C13 C1 117.72(15) . . ?
O1 C14 N2 117.63(15) . . ?
O1 C14 C13 126.14(16) . . ?
N2 C14 C13 116.23(15) . . ?
O2 C15 N3 121.61(17) . . ?
O2 C15 N2 121.79(17) . . ?
N3 C15 N2 116.59(16) . . ?
O3 C16 C13 124.99(16) . . ?
O3 C16 N3 118.40(16) . . ?
C13 C16 N3 116.59(16) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 N1 C9 111.85(13) . . ?
C11 N1 C8 109.91(13) . . ?
C9 N1 C8 109.27(14) . . ?
C11 N1 C1 112.59(13) . . ?
C9 N1 C1 106.89(12) . . ?
C8 N1 C1 106.11(13) . . ?
C15 N2 C14 124.31(15) . . ?
C15 N2 C17 117.78(15) . . ?
C14 N2 C17 117.48(14) . . ?
C15 N3 C16 124.12(15) . . ?
C15 N3 C18 117.36(16) . . ?
C16 N3 C18 118.44(16) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 980643'
