# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H31 N O4'
_chemical_formula_weight         361.47

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)

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

_cell_length_a                   7.7003(6)
_cell_length_b                   8.1539(7)
_cell_length_c                   16.0222(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.409(3)
_cell_angle_gamma                90.00
_cell_volume                     1005.69(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9588
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11752
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3236
_reflns_number_gt                2538
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0507P)²+0.2057P] 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   -0.7(14)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3236
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.0139(3) 0.4161(3) 0.50505(14) 0.0359(5) Uani 1 1 d . . .
O1 O 1.3066(3) 0.2141(3) 0.48669(14) 0.0609(7) Uani 1 1 d . . .
H1A H 1.3882 0.1550 0.4702 0.091 Uiso 1 1 calc R . .
O2 O 1.4145(2) 0.5593(3) 0.58608(12) 0.0495(6) Uani 1 1 d . . .
O3 O 0.8555(2) 0.3393(3) 0.61850(11) 0.0422(5) Uani 1 1 d . . .
O4 O 1.0058(2) 0.3645(2) 0.75345(11) 0.0415(5) Uani 1 1 d . . .
C1 C 1.2443(5) 0.3302(6) 0.3509(2) 0.0774(13) Uani 1 1 d . . .
H1B H 1.3250 0.2537 0.3249 0.116 Uiso 1 1 calc R . .
H1C H 1.2434 0.4341 0.3201 0.116 Uiso 1 1 calc R . .
H1D H 1.1272 0.2830 0.3494 0.116 Uiso 1 1 calc R . .
C2 C 1.3016(4) 0.3607(4) 0.44054(17) 0.0440(7) Uani 1 1 d . . .
H2A H 1.4218 0.4071 0.4405 0.053 Uiso 1 1 calc R . .
C3 C 1.1867(3) 0.4785(4) 0.48885(17) 0.0390(7) Uani 1 1 d . . .
H3A H 1.1775 0.5856 0.4586 0.047 Uiso 1 1 calc R . .
C4 C 0.8744(4) 0.4029(4) 0.44293(18) 0.0478(8) Uani 1 1 d . . .
H4A H 0.7709 0.3577 0.4689 0.072 Uiso 1 1 calc R . .
H4B H 0.9104 0.3303 0.3978 0.072 Uiso 1 1 calc R . .
H4C H 0.8477 0.5118 0.4202 0.072 Uiso 1 1 calc R . .
C5 C 0.9918(3) 0.3975(3) 0.58667(16) 0.0334(6) Uani 1 1 d . . .
C6 C 1.1420(3) 0.4509(3) 0.63499(16) 0.0317(6) Uani 1 1 d . . .
H6A H 1.0929 0.5642 0.6384 0.038 Uiso 1 1 calc R . .
C7 C 1.2665(3) 0.5055(4) 0.57562(17) 0.0370(6) Uani 1 1 d . . .
C8 C 1.1396(3) 0.4364(3) 0.72235(17) 0.0321(6) Uani 1 1 d . . .
C9 C 1.2825(3) 0.4911(4) 0.78323(16) 0.0329(6) Uani 1 1 d . . .
C10 C 1.3261(3) 0.6703(4) 0.76662(18) 0.0420(7) Uani 1 1 d . . .
H10A H 1.2257 0.7390 0.7793 0.063 Uiso 1 1 calc R . .
H10B H 1.3551 0.6840 0.7078 0.063 Uiso 1 1 calc R . .
H10C H 1.4256 0.7031 0.8021 0.063 Uiso 1 1 calc R . .
C11 C 1.4424(3) 0.3784(4) 0.76436(18) 0.0438(7) Uani 1 1 d . . .
H11A H 1.4952 0.4193 0.7119 0.053 Uiso 1 1 calc R . .
C12 C 1.3971(4) 0.1966(5) 0.7512(2) 0.0623(10) Uani 1 1 d . . .
H12A H 1.5030 0.1351 0.7393 0.094 Uiso 1 1 calc R . .
H12B H 1.3142 0.1858 0.7042 0.094 Uiso 1 1 calc R . .
H12C H 1.3452 0.1529 0.8019 0.094 Uiso 1 1 calc R . .
C13 C 1.5787(3) 0.3923(5) 0.8337(2) 0.0547(9) Uani 1 1 d . . .
H13A H 1.6928 0.3561 0.8219 0.066 Uiso 1 1 calc R . .
C14 C 1.5523(4) 0.4501(4) 0.9085(2) 0.0505(8) Uani 1 1 d . . .
H14A H 1.6470 0.4506 0.9476 0.061 Uiso 1 1 calc R . .
C15 C 1.3815(3) 0.5153(4) 0.93584(16) 0.0391(7) Uani 1 1 d . . .
H15A H 1.3901 0.6377 0.9350 0.047 Uiso 1 1 calc R . .
C16 C 1.2300(3) 0.4676(3) 0.87532(16) 0.0338(6) Uani 1 1 d . . .
H16A H 1.2056 0.3483 0.8837 0.041 Uiso 1 1 calc R . .
C17 C 1.0712(3) 0.5631(4) 0.90350(16) 0.0381(7) Uani 1 1 d . . .
H17A H 1.0954 0.6822 0.9004 0.046 Uiso 1 1 calc R . .
H17B H 0.9712 0.5389 0.8655 0.046 Uiso 1 1 calc R . .
C18 C 1.0256(3) 0.5178(4) 0.99231(16) 0.0419(7) Uani 1 1 d . . .
H18A H 0.9938 0.4002 0.9942 0.050 Uiso 1 1 calc R . .
H18B H 0.9232 0.5822 1.0090 0.050 Uiso 1 1 calc R . .
C19 C 1.1745(4) 0.5494(4) 1.05429(17) 0.0422(7) Uani 1 1 d . . .
H19A H 1.1968 0.6702 1.0553 0.051 Uiso 1 1 calc R . .
C20 C 1.1307(4) 0.4971(5) 1.14252(18) 0.0589(9) Uani 1 1 d . . .
H20A H 1.2292 0.5215 1.1804 0.088 Uiso 1 1 calc R . .
H20B H 1.1068 0.3791 1.1433 0.088 Uiso 1 1 calc R . .
H20C H 1.0280 0.5572 1.1606 0.088 Uiso 1 1 calc R . .
C21 C 1.3386(4) 0.4658(4) 1.02470(18) 0.0465(8) Uani 1 1 d . . .
H21A H 1.3230 0.3454 1.0272 0.056 Uiso 1 1 calc R . .
H21B H 1.4371 0.4952 1.0627 0.056 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.332(3) . ?
N1 C4 1.450(3) . ?
N1 C3 1.454(3) . ?
O1 C2 1.406(4) . ?
O2 C7 1.229(3) . ?
O3 C5 1.270(3) . ?
O4 C8 1.296(3) . ?
C1 C2 1.513(4) . ?
C2 C3 1.529(4) . ?
C3 C7 1.522(4) . ?
C5 C6 1.443(3) . ?
C6 C8 1.405(4) . ?
C6 C7 1.438(4) . ?
C8 C9 1.519(4) . ?
C9 C10 1.524(4) . ?
C9 C16 1.551(4) . ?
C9 C11 1.572(4) . ?
C11 C13 1.513(4) . ?
C11 C12 1.536(5) . ?
C13 C14 1.309(4) . ?
C14 C15 1.494(4) . ?
C15 C21 1.524(4) . ?
C15 C16 1.548(3) . ?
C16 C17 1.528(4) . ?
C17 C18 1.520(4) . ?
C18 C19 1.520(4) . ?
C19 C21 1.522(4) . ?
C19 C20 1.522(4) . ?

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
C5 N1 C4 123.7(2) . . ?
C5 N1 C3 110.8(2) . . ?
C4 N1 C3 124.7(2) . . ?
O1 C2 C1 111.3(3) . . ?
O1 C2 C3 106.1(2) . . ?
C1 C2 C3 115.1(3) . . ?
N1 C3 C7 103.8(2) . . ?
N1 C3 C2 114.5(2) . . ?
C7 C3 C2 109.1(2) . . ?
O3 C5 N1 124.3(2) . . ?
O3 C5 C6 123.8(2) . . ?
N1 C5 C6 111.9(2) . . ?
C8 C6 C7 135.3(2) . . ?
C8 C6 C5 118.6(2) . . ?
C7 C6 C5 106.1(2) . . ?
O2 C7 C6 130.7(3) . . ?
O2 C7 C3 121.9(2) . . ?
C6 C7 C3 107.4(2) . . ?
O4 C8 C6 116.8(2) . . ?
O4 C8 C9 117.2(2) . . ?
C6 C8 C9 126.0(2) . . ?
C8 C9 C10 109.2(2) . . ?
C8 C9 C16 111.9(2) . . ?
C10 C9 C16 110.4(2) . . ?
C8 C9 C11 105.2(2) . . ?
C10 C9 C11 110.5(2) . . ?
C16 C9 C11 109.5(2) . . ?
C13 C11 C12 108.9(3) . . ?
C13 C11 C9 110.3(2) . . ?
C12 C11 C9 114.5(2) . . ?
C14 C13 C11 125.3(3) . . ?
C13 C14 C15 123.7(3) . . ?
C14 C15 C21 113.1(2) . . ?
C14 C15 C16 112.4(2) . . ?
C21 C15 C16 110.0(2) . . ?
C17 C16 C15 106.4(2) . . ?
C17 C16 C9 116.6(2) . . ?
C15 C16 C9 110.8(2) . . ?
C18 C17 C16 111.0(2) . . ?
C17 C18 C19 112.5(2) . . ?
C18 C19 C21 109.8(2) . . ?
C18 C19 C20 112.2(2) . . ?
C21 C19 C20 111.6(3) . . ?
C19 C21 C15 111.9(2) . . ?

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
C5 N1 C3 C7 -3.2(3) . . . . ?
C4 N1 C3 C7 166.8(2) . . . . ?
C5 N1 C3 C2 115.6(3) . . . . ?
C4 N1 C3 C2 -74.4(3) . . . . ?
O1 C2 C3 N1 -55.7(3) . . . . ?
C1 C2 C3 N1 67.8(3) . . . . ?
O1 C2 C3 C7 60.1(3) . . . . ?
C1 C2 C3 C7 -176.4(3) . . . . ?
C4 N1 C5 O3 12.5(4) . . . . ?
C3 N1 C5 O3 -177.3(3) . . . . ?
C4 N1 C5 C6 -167.6(2) . . . . ?
C3 N1 C5 C6 2.5(3) . . . . ?
O3 C5 C6 C8 0.9(4) . . . . ?
N1 C5 C6 C8 -178.9(2) . . . . ?
O3 C5 C6 C7 179.2(2) . . . . ?
N1 C5 C6 C7 -0.6(3) . . . . ?
C8 C6 C7 O2 -0.8(6) . . . . ?
C5 C6 C7 O2 -178.8(3) . . . . ?
C8 C6 C7 C3 176.5(3) . . . . ?
C5 C6 C7 C3 -1.4(3) . . . . ?
N1 C3 C7 O2 -179.6(3) . . . . ?
C2 C3 C7 O2 57.9(4) . . . . ?
N1 C3 C7 C6 2.7(3) . . . . ?
C2 C3 C7 C6 -119.7(3) . . . . ?
C7 C6 C8 O4 -173.1(3) . . . . ?
C5 C6 C8 O4 4.7(4) . . . . ?
C7 C6 C8 C9 4.4(5) . . . . ?
C5 C6 C8 C9 -177.8(2) . . . . ?
O4 C8 C9 C10 -129.2(3) . . . . ?
C6 C8 C9 C10 53.3(3) . . . . ?
O4 C8 C9 C16 -6.7(3) . . . . ?
C6 C8 C9 C16 175.8(2) . . . . ?
O4 C8 C9 C11 112.1(3) . . . . ?
C6 C8 C9 C11 -65.3(3) . . . . ?
C8 C9 C11 C13 -166.6(2) . . . . ?
C10 C9 C11 C13 75.7(3) . . . . ?
C16 C9 C11 C13 -46.1(3) . . . . ?
C8 C9 C11 C12 -43.3(3) . . . . ?
C10 C9 C11 C12 -161.1(3) . . . . ?
C16 C9 C11 C12 77.1(3) . . . . ?
C12 C11 C13 C14 -108.6(4) . . . . ?
C9 C11 C13 C14 17.9(5) . . . . ?
C11 C13 C14 C15 -1.5(6) . . . . ?
C13 C14 C15 C21 139.8(3) . . . . ?
C13 C14 C15 C16 14.6(5) . . . . ?
C14 C15 C16 C17 -171.6(2) . . . . ?
C21 C15 C16 C17 61.4(3) . . . . ?
C14 C15 C16 C9 -44.0(3) . . . . ?
C21 C15 C16 C9 -170.9(2) . . . . ?
C8 C9 C16 C17 -61.2(3) . . . . ?
C10 C9 C16 C17 60.6(3) . . . . ?
C11 C9 C16 C17 -177.5(2) . . . . ?
C8 C9 C16 C15 176.9(2) . . . . ?
C10 C9 C16 C15 -61.3(3) . . . . ?
C11 C9 C16 C15 60.6(3) . . . . ?
C15 C16 C17 C18 -60.7(3) . . . . ?
C9 C16 C17 C18 175.2(2) . . . . ?
C16 C17 C18 C19 58.3(3) . . . . ?
C17 C18 C19 C21 -52.8(3) . . . . ?
C17 C18 C19 C20 -177.6(3) . . . . ?
C18 C19 C21 C15 53.9(3) . . . . ?
C20 C19 C21 C15 179.0(2) . . . . ?
C14 C15 C21 C19 173.6(3) . . . . ?
C16 C15 C21 C19 -59.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 1000587'
#######################################################################
#
#                 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_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H38 Cl3 N O5'
_chemical_formula_weight         550.92

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   11.8362(5)
_cell_length_b                   12.2518(5)
_cell_length_c                   19.0137(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2757.27(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9039
_exptl_absorpt_correction_T_max  0.9537
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32519
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4868
_reflns_number_gt                3835
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1358P)²+8.5228P] 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   0.1(2)
_chemical_absolute_configuration .
_refine_ls_number_reflns         4868
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0955
_refine_ls_wR_factor_ref         0.2720
_refine_ls_wR_factor_gt          0.2488
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
Cl3 Cl 0.0306(2) 0.1450(3) 0.0690(2) 0.1039(11) Uani 1 1 d . . .
O1 O 0.6034(4) -0.1990(3) 0.2604(3) 0.0392(11) Uani 1 1 d . . .
O2 O 0.6893(3) 0.0127(4) 0.1418(2) 0.0321(10) Uani 1 1 d . . .
O3 O 0.5997(4) 0.1900(3) 0.2536(2) 0.0304(9) Uani 1 1 d . . .
H3A H 0.5326 0.2124 0.2535 0.046 Uiso 1 1 calc R . .
O4 O 0.5460(4) 0.0873(4) 0.3509(2) 0.0350(10) Uani 1 1 d . . .
O5 O 0.4272(4) 0.1100(3) 0.3363(2) 0.0345(10) Uani 1 1 d . . .
N1 N 0.7220(5) -0.0634(4) 0.2982(3) 0.0325(12) Uani 1 1 d . . .
C1 C 0.3264(5) -0.1771(6) -0.0026(4) 0.0361(15) Uani 1 1 d . . .
H1A H 0.2577 -0.1658 -0.0314 0.043 Uiso 1 1 calc R . .
H1B H 0.3089 -0.2331 0.0333 0.043 Uiso 1 1 calc R . .
C01 C -0.1161(7) 0.1427(8) 0.0631(5) 0.066(2) Uani 1 1 d . . .
H01A H -0.1461 0.0880 0.0974 0.079 Uiso 1 1 calc R . .
C2 C 0.4220(5) -0.2186(5) -0.0499(3) 0.0332(14) Uani 1 1 d . . .
H2A H 0.4355 -0.1626 -0.0872 0.040 Uiso 1 1 calc R . .
C3 C 0.5293(6) -0.2279(5) -0.0059(3) 0.0349(14) Uani 1 1 d . . .
H3B H 0.5179 -0.2841 0.0308 0.042 Uiso 1 1 calc R . .
H3C H 0.5920 -0.2525 -0.0365 0.042 Uiso 1 1 calc R . .
C4 C 0.5625(5) -0.1211(5) 0.0291(3) 0.0292(13) Uani 1 1 d . . .
H4A H 0.5796 -0.0655 -0.0072 0.035 Uiso 1 1 calc R . .
H4B H 0.6311 -0.1320 0.0581 0.035 Uiso 1 1 calc R . .
C5 C 0.4653(5) -0.0819(5) 0.0754(3) 0.0264(12) Uani 1 1 d . . .
H5A H 0.4522 -0.1397 0.1116 0.032 Uiso 1 1 calc R . .
C6 C 0.3568(5) -0.0700(5) 0.0343(3) 0.0295(13) Uani 1 1 d . . .
H6A H 0.3704 -0.0142 -0.0031 0.035 Uiso 1 1 calc R . .
C7 C 0.2628(5) -0.0292(5) 0.0791(4) 0.0349(14) Uani 1 1 d . . .
H7A H 0.1875 -0.0383 0.0627 0.042 Uiso 1 1 calc R . .
C8 C 0.2786(5) 0.0196(5) 0.1412(4) 0.0363(15) Uani 1 1 d . . .
H8A H 0.2139 0.0383 0.1681 0.044 Uiso 1 1 calc R . .
C9 C 0.3939(5) 0.0469(5) 0.1710(3) 0.0265(12) Uani 1 1 d . . .
H9A H 0.3942 0.1262 0.1837 0.032 Uiso 1 1 calc R . .
C10 C 0.4889(5) 0.0276(5) 0.1163(3) 0.0285(13) Uani 1 1 d . . .
C11 C 0.5932(5) 0.0122(5) 0.1621(3) 0.0259(12) Uani 1 1 d . . .
C12 C 0.5587(4) -0.0062(4) 0.2399(3) 0.0223(11) Uani 1 1 d . . .
C13 C 0.4296(5) -0.0196(5) 0.2384(3) 0.0268(12) Uani 1 1 d . . .
H13A H 0.4127 -0.0984 0.2293 0.032 Uiso 1 1 calc R . .
C14 C 0.3760(5) 0.0111(5) 0.3097(3) 0.0308(13) Uani 1 1 d . . .
C15 C 0.6044(5) 0.0894(5) 0.2853(3) 0.0278(13) Uani 1 1 d . . .
C16 C 0.7263(5) 0.0547(5) 0.3068(3) 0.0287(13) Uani 1 1 d . . .
H16A H 0.7361 0.0708 0.3580 0.034 Uiso 1 1 calc R . .
C17 C 0.6287(5) -0.1005(5) 0.2686(3) 0.0289(13) Uani 1 1 d . . .
C18 C 0.3902(7) -0.0831(6) 0.3621(4) 0.0428(16) Uani 1 1 d . . .
H18A H 0.3559 -0.0630 0.4072 0.064 Uiso 1 1 calc R . .
H18B H 0.4708 -0.0980 0.3689 0.064 Uiso 1 1 calc R . .
H18C H 0.3529 -0.1485 0.3436 0.064 Uiso 1 1 calc R . .
C19 C 0.2527(7) 0.0451(7) 0.3060(4) 0.0474(18) Uani 1 1 d . . .
H19A H 0.2256 0.0631 0.3533 0.071 Uiso 1 1 calc R . .
H19B H 0.2077 -0.0151 0.2868 0.071 Uiso 1 1 calc R . .
H19C H 0.2453 0.1092 0.2755 0.071 Uiso 1 1 calc R . .
C20 C 0.3913(8) -0.3259(7) -0.0864(5) 0.062(2) Uani 1 1 d . . .
H20A H 0.4545 -0.3496 -0.1159 0.094 Uiso 1 1 calc R . .
H20B H 0.3241 -0.3150 -0.1157 0.094 Uiso 1 1 calc R . .
H20C H 0.3756 -0.3818 -0.0508 0.094 Uiso 1 1 calc R . .
C21 C 0.7988(7) -0.1387(6) 0.3339(4) 0.051(2) Uani 1 1 d . . .
H21A H 0.7806 -0.2138 0.3204 0.077 Uiso 1 1 calc R . .
H21B H 0.7905 -0.1306 0.3850 0.077 Uiso 1 1 calc R . .
H21C H 0.8768 -0.1221 0.3204 0.077 Uiso 1 1 calc R . .
C22 C 0.8197(5) 0.1161(5) 0.2660(4) 0.0336(14) Uani 1 1 d . . .
H22A H 0.7911 0.1312 0.2175 0.040 Uiso 1 1 calc R . .
C23 C 0.8424(7) 0.2249(6) 0.3017(5) 0.055(2) Uani 1 1 d . . .
H23A H 0.9016 0.2641 0.2760 0.083 Uiso 1 1 calc R . .
H23B H 0.8671 0.2122 0.3502 0.083 Uiso 1 1 calc R . .
H23C H 0.7731 0.2686 0.3019 0.083 Uiso 1 1 calc R . .
C24 C 0.9292(6) 0.0525(6) 0.2595(5) 0.0486(18) Uani 1 1 d . . .
H24A H 0.9845 0.0959 0.2332 0.073 Uiso 1 1 calc R . .
H24B H 0.9150 -0.0161 0.2345 0.073 Uiso 1 1 calc R . .
H24C H 0.9589 0.0366 0.3065 0.073 Uiso 1 1 calc R . .
C25 C 0.5044(6) 0.1256(5) 0.0680(3) 0.0386(15) Uani 1 1 d . . .
H25A H 0.5186 0.1910 0.0963 0.058 Uiso 1 1 calc R . .
H25B H 0.4358 0.1362 0.0400 0.058 Uiso 1 1 calc R . .
H25C H 0.5687 0.1127 0.0366 0.058 Uiso 1 1 calc R . .
Cl2 Cl -0.1473(6) 0.1014(6) -0.01811(19) 0.230(4) Uani 1 1 d . . .
Cl1 Cl -0.1709(7) 0.2640(4) 0.0817(5) 0.322(6) 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
Cl3 C01 1.740(9) . ?
O1 C17 1.253(7) . ?
O2 C11 1.201(7) . ?
O3 C15 1.372(7) . ?
O3 H3A 0.8400 . ?
O4 C15 1.426(7) . ?
O4 O5 1.460(6) . ?
O5 C14 1.446(7) . ?
N1 C17 1.320(8) . ?
N1 C16 1.456(8) . ?
N1 C21 1.463(8) . ?
C1 C6 1.530(9) . ?
C1 C2 1.533(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C01 Cl1 1.659(11) . ?
C01 Cl2 1.667(11) . ?
C01 H01A 1.0000 . ?
C2 C3 1.524(9) . ?
C2 C20 1.530(10) . ?
C2 H2A 1.0000 . ?
C3 C4 1.521(9) . ?
C3 H3B 0.9900 . ?
C3 H3C 0.9900 . ?
C4 C5 1.526(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.510(8) . ?
C5 C10 1.576(8) . ?
C5 H5A 1.0000 . ?
C6 C7 1.489(9) . ?
C6 H6A 1.0000 . ?
C7 C8 1.335(10) . ?
C7 H7A 0.9500 . ?
C8 C9 1.516(9) . ?
C8 H8A 0.9500 . ?
C9 C10 1.550(8) . ?
C9 C13 1.576(8) . ?
C9 H9A 1.0000 . ?
C10 C11 1.522(8) . ?
C10 C25 1.523(9) . ?
C11 C12 1.552(8) . ?
C12 C17 1.523(8) . ?
C12 C13 1.537(8) . ?
C12 C15 1.553(8) . ?
C13 C14 1.544(9) . ?
C13 H13A 1.0000 . ?
C14 C19 1.519(10) . ?
C14 C18 1.533(9) . ?
C15 C16 1.558(8) . ?
C16 C22 1.546(9) . ?
C16 H16A 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 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C24 1.517(9) . ?
C22 C23 1.520(9) . ?
C22 H22A 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C15 O3 H3A 109.5 . . ?
C15 O4 O5 107.3(4) . . ?
C14 O5 O4 108.1(4) . . ?
C17 N1 C16 114.8(5) . . ?
C17 N1 C21 120.0(5) . . ?
C16 N1 C21 123.6(5) . . ?
C6 C1 C2 112.3(5) . . ?
C6 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
C6 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
Cl1 C01 Cl2 112.5(8) . . ?
Cl1 C01 Cl3 111.2(7) . . ?
Cl2 C01 Cl3 106.6(6) . . ?
Cl1 C01 H01A 108.8 . . ?
Cl2 C01 H01A 108.8 . . ?
Cl3 C01 H01A 108.8 . . ?
C3 C2 C20 112.5(6) . . ?
C3 C2 C1 108.6(5) . . ?
C20 C2 C1 112.1(5) . . ?
C3 C2 H2A 107.9 . . ?
C20 C2 H2A 107.9 . . ?
C1 C2 H2A 107.9 . . ?
C4 C3 C2 113.0(5) . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3C 109.0 . . ?
C2 C3 H3C 109.0 . . ?
H3B C3 H3C 107.8 . . ?
C3 C4 C5 109.2(5) . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
C6 C5 C4 111.9(5) . . ?
C6 C5 C10 108.9(5) . . ?
C4 C5 C10 114.8(5) . . ?
C6 C5 H5A 106.9 . . ?
C4 C5 H5A 106.9 . . ?
C10 C5 H5A 106.9 . . ?
C7 C6 C5 111.9(5) . . ?
C7 C6 C1 112.0(5) . . ?
C5 C6 C1 110.8(5) . . ?
C7 C6 H6A 107.3 . . ?
C5 C6 H6A 107.3 . . ?
C1 C6 H6A 107.3 . . ?
C8 C7 C6 123.4(6) . . ?
C8 C7 H7A 118.3 . . ?
C6 C7 H7A 118.3 . . ?
C7 C8 C9 123.8(6) . . ?
C7 C8 H8A 118.1 . . ?
C9 C8 H8A 118.1 . . ?
C8 C9 C10 111.6(5) . . ?
C8 C9 C13 115.6(5) . . ?
C10 C9 C13 105.8(5) . . ?
C8 C9 H9A 107.9 . . ?
C10 C9 H9A 107.9 . . ?
C13 C9 H9A 107.9 . . ?
C11 C10 C25 110.2(5) . . ?
C11 C10 C9 102.9(5) . . ?
C25 C10 C9 111.8(5) . . ?
C11 C10 C5 108.7(5) . . ?
C25 C10 C5 113.2(5) . . ?
C9 C10 C5 109.4(5) . . ?
O2 C11 C10 125.7(5) . . ?
O2 C11 C12 123.8(5) . . ?
C10 C11 C12 110.5(5) . . ?
C17 C12 C13 117.8(5) . . ?
C17 C12 C11 108.0(5) . . ?
C13 C12 C11 105.0(5) . . ?
C17 C12 C15 100.6(4) . . ?
C13 C12 C15 116.0(5) . . ?
C11 C12 C15 109.2(4) . . ?
C12 C13 C14 111.4(5) . . ?
C12 C13 C9 103.1(4) . . ?
C14 C13 C9 118.5(5) . . ?
C12 C13 H13A 107.8 . . ?
C14 C13 H13A 107.8 . . ?
C9 C13 H13A 107.8 . . ?
O5 C14 C19 100.9(5) . . ?
O5 C14 C18 111.0(5) . . ?
C19 C14 C18 110.0(5) . . ?
O5 C14 C13 109.8(5) . . ?
C19 C14 C13 114.9(5) . . ?
C18 C14 C13 110.0(5) . . ?
O3 C15 O4 112.4(5) . . ?
O3 C15 C12 114.7(5) . . ?
O4 C15 C12 107.7(5) . . ?
O3 C15 C16 113.5(5) . . ?
O4 C15 C16 102.4(5) . . ?
C12 C15 C16 105.2(5) . . ?
N1 C16 C22 116.9(5) . . ?
N1 C16 C15 102.1(5) . . ?
C22 C16 C15 113.5(5) . . ?
N1 C16 H16A 108.0 . . ?
C22 C16 H16A 108.0 . . ?
C15 C16 H16A 108.0 . . ?
O1 C17 N1 125.8(6) . . ?
O1 C17 C12 123.8(6) . . ?
N1 C17 C12 110.3(5) . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 C20 H20A 109.5 . . ?
C2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C24 C22 C23 109.6(6) . . ?
C24 C22 C16 113.7(6) . . ?
C23 C22 C16 109.2(6) . . ?
C24 C22 H22A 108.0 . . ?
C23 C22 H22A 108.0 . . ?
C16 C22 H22A 108.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C10 C25 H25A 109.5 . . ?
C10 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C10 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C15 O4 O5 C14 78.6(5) . . . . ?
C6 C1 C2 C3 54.9(7) . . . . ?
C6 C1 C2 C20 179.7(6) . . . . ?
C20 C2 C3 C4 178.5(6) . . . . ?
C1 C2 C3 C4 -56.9(7) . . . . ?
C2 C3 C4 C5 57.7(7) . . . . ?
C3 C4 C5 C6 -56.3(7) . . . . ?
C3 C4 C5 C10 178.9(5) . . . . ?
C4 C5 C6 C7 -178.6(5) . . . . ?
C10 C5 C6 C7 -50.6(7) . . . . ?
C4 C5 C6 C1 55.7(7) . . . . ?
C10 C5 C6 C1 -176.3(5) . . . . ?
C2 C1 C6 C7 178.9(5) . . . . ?
C2 C1 C6 C5 -55.4(7) . . . . ?
C5 C6 C7 C8 17.6(9) . . . . ?
C1 C6 C7 C8 142.7(7) . . . . ?
C6 C7 C8 C9 4.7(10) . . . . ?
C7 C8 C9 C10 8.7(9) . . . . ?
C7 C8 C9 C13 -112.2(7) . . . . ?
C8 C9 C10 C11 -157.1(5) . . . . ?
C13 C9 C10 C11 -30.7(5) . . . . ?
C8 C9 C10 C25 84.6(6) . . . . ?
C13 C9 C10 C25 -148.9(5) . . . . ?
C8 C9 C10 C5 -41.7(6) . . . . ?
C13 C9 C10 C5 84.8(5) . . . . ?
C6 C5 C10 C11 175.6(5) . . . . ?
C4 C5 C10 C11 -58.1(7) . . . . ?
C6 C5 C10 C25 -61.6(7) . . . . ?
C4 C5 C10 C25 64.8(7) . . . . ?
C6 C5 C10 C9 63.9(6) . . . . ?
C4 C5 C10 C9 -169.8(5) . . . . ?
C25 C10 C11 O2 -47.7(8) . . . . ?
C9 C10 C11 O2 -167.0(6) . . . . ?
C5 C10 C11 O2 77.0(7) . . . . ?
C25 C10 C11 C12 133.1(5) . . . . ?
C9 C10 C11 C12 13.7(6) . . . . ?
C5 C10 C11 C12 -102.2(5) . . . . ?
O2 C11 C12 C17 -44.0(7) . . . . ?
C10 C11 C12 C17 135.2(5) . . . . ?
O2 C11 C12 C13 -170.6(5) . . . . ?
C10 C11 C12 C13 8.7(6) . . . . ?
O2 C11 C12 C15 64.5(7) . . . . ?
C10 C11 C12 C15 -116.3(5) . . . . ?
C17 C12 C13 C14 84.7(6) . . . . ?
C11 C12 C13 C14 -155.1(5) . . . . ?
C15 C12 C13 C14 -34.5(7) . . . . ?
C17 C12 C13 C9 -147.2(5) . . . . ?
C11 C12 C13 C9 -27.0(5) . . . . ?
C15 C12 C13 C9 93.6(5) . . . . ?
C8 C9 C13 C12 160.5(5) . . . . ?
C10 C9 C13 C12 36.5(5) . . . . ?
C8 C9 C13 C14 -75.9(7) . . . . ?
C10 C9 C13 C14 160.1(5) . . . . ?
O4 O5 C14 C19 173.5(4) . . . . ?
O4 O5 C14 C18 57.0(6) . . . . ?
O4 O5 C14 C13 -64.8(5) . . . . ?
C12 C13 C14 O5 43.3(6) . . . . ?
C9 C13 C14 O5 -76.1(6) . . . . ?
C12 C13 C14 C19 156.2(5) . . . . ?
C9 C13 C14 C19 36.9(8) . . . . ?
C12 C13 C14 C18 -79.1(6) . . . . ?
C9 C13 C14 C18 161.6(5) . . . . ?
O5 O4 C15 O3 62.5(6) . . . . ?
O5 O4 C15 C12 -64.8(5) . . . . ?
O5 O4 C15 C16 -175.3(4) . . . . ?
C17 C12 C15 O3 151.4(5) . . . . ?
C13 C12 C15 O3 -80.4(6) . . . . ?
C11 C12 C15 O3 38.0(6) . . . . ?
C17 C12 C15 O4 -82.7(5) . . . . ?
C13 C12 C15 O4 45.6(6) . . . . ?
C11 C12 C15 O4 163.9(4) . . . . ?
C17 C12 C15 C16 26.0(6) . . . . ?
C13 C12 C15 C16 154.2(5) . . . . ?
C11 C12 C15 C16 -87.4(5) . . . . ?
C17 N1 C16 C22 -116.6(6) . . . . ?
C21 N1 C16 C22 77.9(8) . . . . ?
C17 N1 C16 C15 7.9(7) . . . . ?
C21 N1 C16 C15 -157.6(6) . . . . ?
O3 C15 C16 N1 -147.6(5) . . . . ?
O4 C15 C16 N1 91.0(5) . . . . ?
C12 C15 C16 N1 -21.4(6) . . . . ?
O3 C15 C16 C22 -20.9(7) . . . . ?
O4 C15 C16 C22 -142.3(5) . . . . ?
C12 C15 C16 C22 105.3(5) . . . . ?
C16 N1 C17 O1 -174.9(6) . . . . ?
C21 N1 C17 O1 -8.8(10) . . . . ?
C16 N1 C17 C12 9.6(7) . . . . ?
C21 N1 C17 C12 175.7(6) . . . . ?
C13 C12 C17 O1 35.0(8) . . . . ?
C11 C12 C17 O1 -83.7(7) . . . . ?
C15 C12 C17 O1 162.0(6) . . . . ?
C13 C12 C17 N1 -149.4(5) . . . . ?
C11 C12 C17 N1 91.9(6) . . . . ?
C15 C12 C17 N1 -22.4(6) . . . . ?
N1 C16 C22 C24 -34.7(8) . . . . ?
C15 C16 C22 C24 -153.2(6) . . . . ?
N1 C16 C22 C23 -157.5(6) . . . . ?
C15 C16 C22 C23 84.0(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.284
_refine_diff_density_min         -0.986
_refine_diff_density_rms         0.099
_database_code_depnum_ccdc_archive 'CCDC 1000588'
#######################################################################
#
#                 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_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H37 N O4'
_chemical_formula_weight         415.56

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   P2(1)2(1)2(1)

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

_cell_length_a                   6.8794(5)
_cell_length_b                   14.9305(10)
_cell_length_c                   22.2706(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2287.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26907
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4021
_reflns_number_gt                3003
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0393P)²+0.4065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.6(13)
_chemical_absolute_configuration .
_refine_ls_number_reflns         4021
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
O1 O 0.0402(2) 0.69430(12) 0.20610(9) 0.0377(5) Uani 1 1 d . . .
O2 O 0.6930(2) 0.61324(12) 0.23472(8) 0.0391(4) Uani 1 1 d . . .
O3 O 0.3697(3) 0.75616(11) 0.29552(7) 0.0438(5) Uani 1 1 d . . .
O4 O 0.1121(2) 0.55286(10) 0.17335(8) 0.0337(4) Uani 1 1 d . . .
N1 N 0.5105(3) 0.66097(13) 0.15459(8) 0.0286(5) Uani 1 1 d . . .
C1 C 0.3685(4) 0.60604(16) 0.39413(11) 0.0323(6) Uani 1 1 d . . .
H1B H 0.4691 0.5681 0.3740 0.039 Uiso 1 1 calc R . .
C2 C 0.4758(4) 0.68483(17) 0.42228(12) 0.0451(7) Uani 1 1 d . . .
H2A H 0.5413 0.7199 0.3904 0.054 Uiso 1 1 calc R . .
H2B H 0.3815 0.7246 0.4427 0.054 Uiso 1 1 calc R . .
C3 C 0.6256(5) 0.65203(19) 0.46727(12) 0.0508(8) Uani 1 1 d . . .
H3A H 0.6898 0.7045 0.4859 0.061 Uiso 1 1 calc R . .
H3B H 0.7264 0.6173 0.4457 0.061 Uiso 1 1 calc R . .
C4 C 0.5389(4) 0.59370(18) 0.51662(12) 0.0438(7) Uani 1 1 d . . .
H4A H 0.4456 0.6308 0.5404 0.053 Uiso 1 1 calc R . .
C5 C 0.4275(4) 0.51684(18) 0.48802(12) 0.0453(7) Uani 1 1 d . . .
H5A H 0.3627 0.4818 0.5200 0.054 Uiso 1 1 calc R . .
H5B H 0.5208 0.4767 0.4675 0.054 Uiso 1 1 calc R . .
C6 C 0.2749(4) 0.54762(19) 0.44280(11) 0.0410(7) Uani 1 1 d . . .
H6A H 0.1780 0.5853 0.4647 0.049 Uiso 1 1 calc R . .
C7 C 0.1684(4) 0.47072(19) 0.41515(13) 0.0484(8) Uani 1 1 d . . .
H7A H 0.1373 0.4211 0.4401 0.058 Uiso 1 1 calc R . .
C8 C 0.1150(4) 0.46751(19) 0.35854(13) 0.0464(7) Uani 1 1 d . . .
H8A H 0.0562 0.4140 0.3444 0.056 Uiso 1 1 calc R . .
C9 C 0.1412(4) 0.54343(16) 0.31471(11) 0.0353(6) Uani 1 1 d . . .
H9A H 0.0114 0.5567 0.2966 0.042 Uiso 1 1 calc R . .
C10 C 0.2149(4) 0.63021(16) 0.34505(11) 0.0328(6) Uani 1 1 d . . .
C11 C 0.3153(3) 0.67932(16) 0.29412(11) 0.0298(6) Uani 1 1 d . . .
C12 C 0.3401(3) 0.61783(15) 0.24019(10) 0.0257(5) Uani 1 1 d . . .
C13 C 0.2853(3) 0.52386(15) 0.26239(11) 0.0302(6) Uani 1 1 d . . .
H13A H 0.4024 0.4908 0.2771 0.036 Uiso 1 1 calc R . .
C14 C 0.1989(4) 0.47844(15) 0.20679(12) 0.0364(6) Uani 1 1 d . . .
C15 C 0.1915(3) 0.63669(15) 0.18974(11) 0.0281(6) Uani 1 1 d . . .
C16 C 0.3089(3) 0.67544(16) 0.13621(11) 0.0301(6) Uani 1 1 d . . .
H16A H 0.2836 0.6363 0.1006 0.036 Uiso 1 1 calc R . .
C17 C 0.5353(3) 0.62989(16) 0.21049(11) 0.0290(6) Uani 1 1 d . . .
C18 C 0.6713(4) 0.6695(3) 0.11267(14) 0.0438(7) Uani 1 1 d . . .
H18A H 0.709(4) 0.7310(19) 0.1089(12) 0.048(9) Uiso 1 1 d . . .
H18B H 0.783(4) 0.6298(17) 0.1263(11) 0.044(8) Uiso 1 1 d . . .
H18C H 0.627(4) 0.6510(17) 0.0716(13) 0.056(8) Uiso 1 1 d . . .
C19 C 0.2628(4) 0.77275(16) 0.11754(12) 0.0380(7) Uani 1 1 d . . .
H19A H 0.1192 0.7801 0.1224 0.046 Uiso 1 1 calc R . .
C20 C 0.3554(4) 0.84256(16) 0.15761(12) 0.0413(7) Uani 1 1 d . . .
H20A H 0.3201 0.9025 0.1433 0.062 Uiso 1 1 calc R . .
H20B H 0.4970 0.8358 0.1566 0.062 Uiso 1 1 calc R . .
H20C H 0.3090 0.8347 0.1989 0.062 Uiso 1 1 calc R . .
C21 C 0.3051(5) 0.7905(2) 0.05197(12) 0.0571(9) Uani 1 1 d . . .
H21A H 0.2733 0.8528 0.0424 0.086 Uiso 1 1 calc R . .
H21B H 0.2262 0.7504 0.0271 0.086 Uiso 1 1 calc R . .
H21C H 0.4432 0.7796 0.0440 0.086 Uiso 1 1 calc R . .
C22 C 0.3554(5) 0.43593(19) 0.16834(13) 0.0523(8) Uani 1 1 d . . .
H22A H 0.2956 0.4080 0.1331 0.078 Uiso 1 1 calc R . .
H22B H 0.4242 0.3903 0.1918 0.078 Uiso 1 1 calc R . .
H22C H 0.4476 0.4820 0.1553 0.078 Uiso 1 1 calc R . .
C23 C 0.0333(5) 0.41275(18) 0.21812(14) 0.0565(9) Uani 1 1 d . . .
H23A H -0.0121 0.3883 0.1798 0.085 Uiso 1 1 calc R . .
H23B H -0.0740 0.4439 0.2382 0.085 Uiso 1 1 calc R . .
H23C H 0.0795 0.3638 0.2437 0.085 Uiso 1 1 calc R . .
C24 C 0.6964(5) 0.5596(2) 0.55873(13) 0.0586(9) Uani 1 1 d . . .
H24A H 0.6373 0.5226 0.5901 0.088 Uiso 1 1 calc R . .
H24B H 0.7632 0.6106 0.5772 0.088 Uiso 1 1 calc R . .
H24C H 0.7902 0.5237 0.5360 0.088 Uiso 1 1 calc R . .
C25 C 0.0496(4) 0.6885(2) 0.36957(14) 0.0538(8) Uani 1 1 d . . .
H25A H -0.0435 0.7011 0.3373 0.081 Uiso 1 1 calc R . .
H25B H 0.1030 0.7449 0.3848 0.081 Uiso 1 1 calc R . .
H25C H -0.0165 0.6566 0.4022 0.081 Uiso 1 1 calc R . .
H1A H -0.054(4) 0.6613(19) 0.2140(13) 0.060(10) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.398(3) . ?
O1 H1A 0.83(3) . ?
O2 C17 1.237(3) . ?
O3 C11 1.207(3) . ?
O4 C15 1.414(3) . ?
O4 C14 1.465(3) . ?
N1 C17 1.339(3) . ?
N1 C18 1.453(3) . ?
N1 C16 1.462(3) . ?
C1 C2 1.524(3) . ?
C1 C6 1.533(3) . ?
C1 C10 1.562(4) . ?
C1 H1B 1.0000 . ?
C2 C3 1.519(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.524(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.520(4) . ?
C4 C24 1.520(4) . ?
C4 H4A 1.0000 . ?
C5 C6 1.526(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.495(4) . ?
C6 H6A 1.0000 . ?
C7 C8 1.314(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.507(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.547(3) . ?
C9 C13 1.558(3) . ?
C9 H9A 1.0000 . ?
C10 C11 1.517(3) . ?
C10 C25 1.532(4) . ?
C11 C12 1.521(3) . ?
C12 C17 1.507(3) . ?
C12 C13 1.535(3) . ?
C12 C15 1.545(3) . ?
C13 C14 1.532(3) . ?
C13 H13A 1.0000 . ?
C14 C22 1.515(4) . ?
C14 C23 1.524(4) . ?
C15 C16 1.552(3) . ?
C16 C19 1.544(3) . ?
C16 H16A 1.0000 . ?
C18 H18A 0.96(3) . ?
C18 H18B 1.02(3) . ?
C18 H18C 1.00(3) . ?
C19 C21 1.512(4) . ?
C19 C20 1.513(3) . ?
C19 H19A 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C15 O1 H1A 106(2) . . ?
C15 O4 C14 112.50(17) . . ?
C17 N1 C18 122.1(2) . . ?
C17 N1 C16 115.60(19) . . ?
C18 N1 C16 122.0(2) . . ?
C2 C1 C6 110.6(2) . . ?
C2 C1 C10 115.9(2) . . ?
C6 C1 C10 110.0(2) . . ?
C2 C1 H1B 106.6 . . ?
C6 C1 H1B 106.6 . . ?
C10 C1 H1B 106.6 . . ?
C3 C2 C1 110.6(2) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C2 C3 C4 113.2(2) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C24 111.4(2) . . ?
C5 C4 C3 109.1(2) . . ?
C24 C4 C3 110.9(2) . . ?
C5 C4 H4A 108.5 . . ?
C24 C4 H4A 108.5 . . ?
C3 C4 H4A 108.5 . . ?
C4 C5 C6 113.3(2) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C5 112.2(2) . . ?
C7 C6 C1 110.6(2) . . ?
C5 C6 C1 110.4(2) . . ?
C7 C6 H6A 107.8 . . ?
C5 C6 H6A 107.8 . . ?
C1 C6 H6A 107.8 . . ?
C8 C7 C6 124.1(2) . . ?
C8 C7 H7A 118.0 . . ?
C6 C7 H7A 118.0 . . ?
C7 C8 C9 124.1(3) . . ?
C7 C8 H8A 118.0 . . ?
C9 C8 H8A 118.0 . . ?
C8 C9 C10 112.7(2) . . ?
C8 C9 C13 114.8(2) . . ?
C10 C9 C13 105.98(19) . . ?
C8 C9 H9A 107.7 . . ?
C10 C9 H9A 107.7 . . ?
C13 C9 H9A 107.7 . . ?
C11 C10 C25 109.3(2) . . ?
C11 C10 C9 103.15(19) . . ?
C25 C10 C9 112.8(2) . . ?
C11 C10 C1 109.08(19) . . ?
C25 C10 C1 112.6(2) . . ?
C9 C10 C1 109.5(2) . . ?
O3 C11 C10 125.5(2) . . ?
O3 C11 C12 124.0(2) . . ?
C10 C11 C12 110.5(2) . . ?
C17 C12 C11 111.98(18) . . ?
C17 C12 C13 118.00(19) . . ?
C11 C12 C13 105.65(19) . . ?
C17 C12 C15 104.40(19) . . ?
C11 C12 C15 112.93(18) . . ?
C13 C12 C15 103.79(18) . . ?
C14 C13 C12 103.86(19) . . ?
C14 C13 C9 116.2(2) . . ?
C12 C13 C9 103.06(18) . . ?
C14 C13 H13A 111.1 . . ?
C12 C13 H13A 111.1 . . ?
C9 C13 H13A 111.1 . . ?
O4 C14 C22 108.7(2) . . ?
O4 C14 C23 105.5(2) . . ?
C22 C14 C23 110.8(2) . . ?
O4 C14 C13 103.50(18) . . ?
C22 C14 C13 111.5(2) . . ?
C23 C14 C13 116.2(2) . . ?
O1 C15 O4 108.92(18) . . ?
O1 C15 C12 114.53(19) . . ?
O4 C15 C12 106.39(17) . . ?
O1 C15 C16 110.99(19) . . ?
O4 C15 C16 109.45(19) . . ?
C12 C15 C16 106.38(17) . . ?
N1 C16 C19 114.2(2) . . ?
N1 C16 C15 102.92(18) . . ?
C19 C16 C15 116.8(2) . . ?
N1 C16 H16A 107.5 . . ?
C19 C16 H16A 107.5 . . ?
C15 C16 H16A 107.5 . . ?
O2 C17 N1 125.9(2) . . ?
O2 C17 C12 124.5(2) . . ?
N1 C17 C12 109.6(2) . . ?
N1 C18 H18A 110.2(17) . . ?
N1 C18 H18B 109.5(14) . . ?
H18A C18 H18B 112(2) . . ?
N1 C18 H18C 109.5(17) . . ?
H18A C18 H18C 105(2) . . ?
H18B C18 H18C 110(2) . . ?
C21 C19 C20 111.6(2) . . ?
C21 C19 C16 112.6(2) . . ?
C20 C19 C16 113.8(2) . . ?
C21 C19 H19A 106.0 . . ?
C20 C19 H19A 106.0 . . ?
C16 C19 H19A 106.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 C23 H23A 109.5 . . ?
C14 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C14 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C4 C24 H24A 109.5 . . ?
C4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C10 C25 H25A 109.5 . . ?
C10 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C10 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C6 C1 C2 C3 56.1(3) . . . . ?
C10 C1 C2 C3 -177.8(2) . . . . ?
C1 C2 C3 C4 -56.7(3) . . . . ?
C2 C3 C4 C5 54.5(3) . . . . ?
C2 C3 C4 C24 177.6(2) . . . . ?
C24 C4 C5 C6 -176.9(2) . . . . ?
C3 C4 C5 C6 -54.1(3) . . . . ?
C4 C5 C6 C7 179.7(2) . . . . ?
C4 C5 C6 C1 55.8(3) . . . . ?
C2 C1 C6 C7 179.6(2) . . . . ?
C10 C1 C6 C7 50.2(3) . . . . ?
C2 C1 C6 C5 -55.6(3) . . . . ?
C10 C1 C6 C5 175.0(2) . . . . ?
C5 C6 C7 C8 -141.8(3) . . . . ?
C1 C6 C7 C8 -18.0(4) . . . . ?
C6 C7 C8 C9 -4.5(5) . . . . ?
C7 C8 C9 C10 -7.0(4) . . . . ?
C7 C8 C9 C13 114.5(3) . . . . ?
C8 C9 C10 C11 155.1(2) . . . . ?
C13 C9 C10 C11 28.7(2) . . . . ?
C8 C9 C10 C25 -87.1(3) . . . . ?
C13 C9 C10 C25 146.5(2) . . . . ?
C8 C9 C10 C1 39.1(3) . . . . ?
C13 C9 C10 C1 -87.3(2) . . . . ?
C2 C1 C10 C11 59.7(3) . . . . ?
C6 C1 C10 C11 -173.9(2) . . . . ?
C2 C1 C10 C25 -61.8(3) . . . . ?
C6 C1 C10 C25 64.6(3) . . . . ?
C2 C1 C10 C9 171.9(2) . . . . ?
C6 C1 C10 C9 -61.7(2) . . . . ?
C25 C10 C11 O3 48.4(3) . . . . ?
C9 C10 C11 O3 168.6(2) . . . . ?
C1 C10 C11 O3 -75.0(3) . . . . ?
C25 C10 C11 C12 -132.0(2) . . . . ?
C9 C10 C11 C12 -11.8(3) . . . . ?
C1 C10 C11 C12 104.6(2) . . . . ?
O3 C11 C12 C17 40.1(3) . . . . ?
C10 C11 C12 C17 -139.5(2) . . . . ?
O3 C11 C12 C13 169.8(2) . . . . ?
C10 C11 C12 C13 -9.8(2) . . . . ?
O3 C11 C12 C15 -77.4(3) . . . . ?
C10 C11 C12 C15 103.0(2) . . . . ?
C17 C12 C13 C14 -85.4(2) . . . . ?
C11 C12 C13 C14 148.49(19) . . . . ?
C15 C12 C13 C14 29.5(2) . . . . ?
C17 C12 C13 C9 153.0(2) . . . . ?
C11 C12 C13 C9 26.9(2) . . . . ?
C15 C12 C13 C9 -92.1(2) . . . . ?
C8 C9 C13 C14 87.1(3) . . . . ?
C10 C9 C13 C14 -147.8(2) . . . . ?
C8 C9 C13 C12 -160.0(2) . . . . ?
C10 C9 C13 C12 -34.9(2) . . . . ?
C15 O4 C14 C22 -97.9(2) . . . . ?
C15 O4 C14 C23 143.3(2) . . . . ?
C15 O4 C14 C13 20.8(3) . . . . ?
C12 C13 C14 O4 -30.6(2) . . . . ?
C9 C13 C14 O4 81.8(2) . . . . ?
C12 C13 C14 C22 86.1(2) . . . . ?
C9 C13 C14 C22 -161.5(2) . . . . ?
C12 C13 C14 C23 -145.7(2) . . . . ?
C9 C13 C14 C23 -33.3(3) . . . . ?
C14 O4 C15 O1 -126.0(2) . . . . ?
C14 O4 C15 C12 -2.0(3) . . . . ?
C14 O4 C15 C16 112.5(2) . . . . ?
C17 C12 C15 O1 -132.9(2) . . . . ?
C11 C12 C15 O1 -11.1(3) . . . . ?
C13 C12 C15 O1 102.9(2) . . . . ?
C17 C12 C15 O4 106.7(2) . . . . ?
C11 C12 C15 O4 -131.44(19) . . . . ?
C13 C12 C15 O4 -17.5(2) . . . . ?
C17 C12 C15 C16 -10.0(2) . . . . ?
C11 C12 C15 C16 111.9(2) . . . . ?
C13 C12 C15 C16 -134.16(19) . . . . ?
C17 N1 C16 C19 121.1(2) . . . . ?
C18 N1 C16 C19 -66.0(3) . . . . ?
C17 N1 C16 C15 -6.4(3) . . . . ?
C18 N1 C16 C15 166.5(2) . . . . ?
O1 C15 C16 N1 135.02(19) . . . . ?
O4 C15 C16 N1 -104.7(2) . . . . ?
C12 C15 C16 N1 9.8(2) . . . . ?
O1 C15 C16 C19 9.1(3) . . . . ?
O4 C15 C16 C19 129.4(2) . . . . ?
C12 C15 C16 C19 -116.1(2) . . . . ?
C18 N1 C17 O2 7.1(4) . . . . ?
C16 N1 C17 O2 -180.0(2) . . . . ?
C18 N1 C17 C12 -172.8(2) . . . . ?
C16 N1 C17 C12 0.1(3) . . . . ?
C11 C12 C17 O2 63.9(3) . . . . ?
C13 C12 C17 O2 -59.1(3) . . . . ?
C15 C12 C17 O2 -173.6(2) . . . . ?
C11 C12 C17 N1 -116.1(2) . . . . ?
C13 C12 C17 N1 120.9(2) . . . . ?
C15 C12 C17 N1 6.4(2) . . . . ?
N1 C16 C19 C21 87.0(3) . . . . ?
C15 C16 C19 C21 -152.9(2) . . . . ?
N1 C16 C19 C20 -41.3(3) . . . . ?
C15 C16 C19 C20 78.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 1000589'
