# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

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

data_FO6273
_database_code_depnum_ccdc_archive 'CCDC 1820196'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H25 N3 O4'
_chemical_formula_sum            'C21 H25 N3 O4'
_chemical_formula_weight         383.44

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   11.6451(6)
_cell_length_b                   15.7066(7)
_cell_length_c                   11.7436(6)
_cell_angle_alpha                90
_cell_angle_beta                 117.744(2)
_cell_angle_gamma                90
_cell_volume                     1901.02(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    12803
_cell_measurement_theta_min      2.03
_cell_measurement_theta_max      27.33

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.078
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6223
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12803
_diffrn_reflns_av_R_equivalents  0.1051
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         27.33
_reflns_number_total             4248
_reflns_number_gt                2805
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_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)+(0.0261P)²+2.4934P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4248
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0846
_refine_ls_wR_factor_ref         0.1607
_refine_ls_wR_factor_gt          0.1425
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.186
_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 0.7294(2) 0.17674(16) 0.5419(2) 0.0310(6) Uani 1 1 d . . .
O2 O 0.4000(2) 0.04365(14) 0.5983(2) 0.0279(5) Uani 1 1 d . . .
O3 O 0.7529(2) 0.62465(15) 0.2863(2) 0.0299(6) Uani 1 1 d . . .
O4 O 0.9408(2) 0.88307(15) 0.2593(2) 0.0318(6) Uani 1 1 d . . .
N1 N 0.6364(2) 0.41996(16) 0.6380(2) 0.0234(6) Uani 1 1 d . . .
N2 N 0.7840(2) 0.33603(17) 0.6035(3) 0.0238(6) Uani 1 1 d . . .
N3 N 0.8142(2) 0.56068(17) 0.5129(2) 0.0234(6) Uani 1 1 d . . .
C1 C 0.6423(3) 0.34924(19) 0.5583(3) 0.0203(6) Uani 1 1 d . . .
H1A H 0.5991 0.3665 0.4656 0.024 Uiso 1 1 calc R . .
C2 C 0.6724(3) 0.4988(2) 0.5926(3) 0.0230(7) Uani 1 1 d . . .
H2A H 0.6702 0.5472 0.6455 0.028 Uiso 1 1 calc R . .
H2B H 0.6066 0.5097 0.5026 0.028 Uiso 1 1 calc R . .
C3 C 0.8078(3) 0.4953(2) 0.5987(3) 0.0237(7) Uani 1 1 d . . .
H3A H 0.8763 0.5063 0.6888 0.028 Uiso 1 1 calc R . .
C4 C 0.8311(3) 0.4075(2) 0.5536(3) 0.0257(7) Uani 1 1 d . . .
H4A H 0.7862 0.4058 0.4584 0.031 Uiso 1 1 calc R . .
H4B H 0.9251 0.4002 0.5829 0.031 Uiso 1 1 calc R . .
C5 C 0.7385(3) 0.3955(2) 0.7680(3) 0.0263(7) Uani 1 1 d . . .
H5A H 0.7007 0.3620 0.8139 0.032 Uiso 1 1 calc R . .
H5B H 0.7810 0.4467 0.8195 0.032 Uiso 1 1 calc R . .
C6 C 0.8379(3) 0.3407(2) 0.7458(3) 0.0292(8) Uani 1 1 d . . .
H6A H 0.9245 0.3680 0.7855 0.035 Uiso 1 1 calc R . .
H6B H 0.8459 0.2831 0.7830 0.035 Uiso 1 1 calc R . .
C7 C 0.5797(3) 0.2686(2) 0.5750(3) 0.0205(7) Uani 1 1 d . . .
C8 C 0.4693(3) 0.2725(2) 0.5918(3) 0.0235(7) Uani 1 1 d . . .
H8A H 0.4368 0.3266 0.5986 0.028 Uiso 1 1 calc R . .
C9 C 0.4046(3) 0.1995(2) 0.5989(3) 0.0245(7) Uani 1 1 d . . .
H9A H 0.3295 0.2041 0.6108 0.029 Uiso 1 1 calc R . .
C10 C 0.4514(3) 0.1201(2) 0.5883(3) 0.0223(7) Uani 1 1 d . . .
C11 C 0.5610(3) 0.1144(2) 0.5697(3) 0.0231(7) Uani 1 1 d . . .
H11A H 0.5926 0.0601 0.5619 0.028 Uiso 1 1 calc R . .
C12 C 0.6240(3) 0.1874(2) 0.5625(3) 0.0215(7) Uani 1 1 d . . .
C13 C 0.8889(3) 0.6252(2) 0.5630(3) 0.0225(7) Uani 1 1 d . . .
H13A H 0.9364 0.6293 0.6540 0.027 Uiso 1 1 calc R . .
C14 C 0.9032(3) 0.6922(2) 0.4850(3) 0.0209(7) Uani 1 1 d . . .
C15 C 0.9868(3) 0.7607(2) 0.5438(3) 0.0235(7) Uani 1 1 d . . .
H15A H 1.0332 0.7628 0.6351 0.028 Uiso 1 1 calc R . .
C16 C 1.0043(3) 0.8254(2) 0.4738(3) 0.0239(7) Uani 1 1 d . . .
H16A H 1.0618 0.8713 0.5157 0.029 Uiso 1 1 calc R . .
C17 C 0.9351(3) 0.8218(2) 0.3392(3) 0.0249(7) Uani 1 1 d . . .
C18 C 0.8521(3) 0.7541(2) 0.2771(3) 0.0243(7) Uani 1 1 d . . .
H18A H 0.8064 0.7523 0.1858 0.029 Uiso 1 1 calc R . .
C19 C 0.8365(3) 0.6896(2) 0.3491(3) 0.0250(7) Uani 1 1 d . . .
C20 C 0.2908(3) 0.0448(2) 0.6226(4) 0.0341(8) Uani 1 1 d . . .
H20A H 0.2655 -0.0137 0.6293 0.051 Uiso 1 1 calc R . .
H20B H 0.2183 0.0740 0.5518 0.051 Uiso 1 1 calc R . .
H20C H 0.3137 0.0751 0.7033 0.051 Uiso 1 1 calc R . .
C21 C 1.0158(3) 0.9581(2) 0.3164(3) 0.0293(8) Uani 1 1 d . . .
H21A H 1.0113 0.9964 0.2486 0.044 Uiso 1 1 calc R . .
H21B H 1.1063 0.9421 0.3721 0.044 Uiso 1 1 calc R . .
H21C H 0.9810 0.9870 0.3677 0.044 Uiso 1 1 calc R . .
H1O1 H 0.782(5) 0.241(3) 0.558(5) 0.096(18) Uiso 1 1 d . . .
H1O3 H 0.759(5) 0.585(3) 0.352(5) 0.086(18) 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 C12 1.368(4) . ?
O1 H1O1 1.14(5) . ?
O2 C10 1.371(4) . ?
O2 C20 1.427(4) . ?
O3 C19 1.365(4) . ?
O3 H1O3 0.97(5) . ?
O4 C17 1.368(4) . ?
O4 C21 1.433(4) . ?
N1 C1 1.475(4) . ?
N1 C2 1.483(4) . ?
N1 C5 1.484(4) . ?
N2 C4 1.484(4) . ?
N2 C6 1.488(4) . ?
N2 C1 1.494(4) . ?
N3 C13 1.286(4) . ?
N3 C3 1.464(4) . ?
C1 C7 1.520(4) . ?
C1 H1A 1.0000 . ?
C2 C3 1.546(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.546(4) . ?
C3 H3A 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.559(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.389(4) . ?
C7 C12 1.408(4) . ?
C8 C9 1.395(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.391(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.394(4) . ?
C11 C12 1.386(4) . ?
C11 H11A 0.9500 . ?
C13 C14 1.455(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.399(4) . ?
C14 C19 1.413(4) . ?
C15 C16 1.381(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.401(4) . ?
C16 H16A 0.9500 . ?
C17 C18 1.392(4) . ?
C18 C19 1.385(5) . ?
C18 H18A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C12 O1 H1O1 108(3) . . ?
C10 O2 C20 118.1(3) . . ?
C19 O3 H1O3 106(3) . . ?
C17 O4 C21 118.1(3) . . ?
C1 N1 C2 107.2(2) . . ?
C1 N1 C5 101.9(2) . . ?
C2 N1 C5 111.2(2) . . ?
C4 N2 C6 111.5(3) . . ?
C4 N2 C1 107.7(2) . . ?
C6 N2 C1 102.2(2) . . ?
C13 N3 C3 118.6(3) . . ?
N1 C1 N2 104.4(2) . . ?
N1 C1 C7 112.2(2) . . ?
N2 C1 C7 110.8(2) . . ?
N1 C1 H1A 109.7 . . ?
N2 C1 H1A 109.7 . . ?
C7 C1 H1A 109.7 . . ?
N1 C2 C3 114.0(2) . . ?
N1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
N1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
N3 C3 C4 108.5(3) . . ?
N3 C3 C2 108.7(2) . . ?
C4 C3 C2 110.7(3) . . ?
N3 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
N2 C4 C3 112.6(3) . . ?
N2 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
N2 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 C6 105.8(2) . . ?
N1 C5 H5A 110.6 . . ?
C6 C5 H5A 110.6 . . ?
N1 C5 H5B 110.6 . . ?
C6 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
N2 C6 C5 104.9(2) . . ?
N2 C6 H6A 110.8 . . ?
C5 C6 H6A 110.8 . . ?
N2 C6 H6B 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.8 . . ?
C8 C7 C12 117.6(3) . . ?
C8 C7 C1 120.9(3) . . ?
C12 C7 C1 121.3(3) . . ?
C7 C8 C9 122.3(3) . . ?
C7 C8 H8A 118.9 . . ?
C9 C8 H8A 118.9 . . ?
C10 C9 C8 119.1(3) . . ?
C10 C9 H9A 120.5 . . ?
C8 C9 H9A 120.5 . . ?
O2 C10 C9 125.0(3) . . ?
O2 C10 C11 115.2(3) . . ?
C9 C10 C11 119.8(3) . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
O1 C12 C11 117.0(3) . . ?
O1 C12 C7 122.2(3) . . ?
C11 C12 C7 120.8(3) . . ?
N3 C13 C14 122.3(3) . . ?
N3 C13 H13A 118.9 . . ?
C14 C13 H13A 118.9 . . ?
C15 C14 C19 118.1(3) . . ?
C15 C14 C13 120.2(3) . . ?
C19 C14 C13 121.7(3) . . ?
C16 C15 C14 122.2(3) . . ?
C16 C15 H15A 118.9 . . ?
C14 C15 H15A 118.9 . . ?
C15 C16 C17 118.4(3) . . ?
C15 C16 H16A 120.8 . . ?
C17 C16 H16A 120.8 . . ?
O4 C17 C18 114.9(3) . . ?
O4 C17 C16 124.0(3) . . ?
C18 C17 C16 121.1(3) . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18A 120.2 . . ?
C17 C18 H18A 120.2 . . ?
O3 C19 C18 118.7(3) . . ?
O3 C19 C14 120.7(3) . . ?
C18 C19 C14 120.5(3) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.33
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.062
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FO6218
_database_code_depnum_ccdc_archive 'CCDC 1820198'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H43 N3 O6'
_chemical_formula_sum            'C32 H43 N3 O6'
_chemical_formula_weight         565.69

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


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

_cell_length_a                   7.2228(2)
_cell_length_b                   11.9597(3)
_cell_length_c                   17.8857(4)
_cell_angle_alpha                77.175(2)
_cell_angle_beta                 87.679(2)
_cell_angle_gamma                79.603(1)
_cell_volume                     1481.73(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    9072
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.44

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.088
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4405
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9072
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         27.44
_reflns_number_total             6573
_reflns_number_gt                5403
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_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)+(0.0000P)²+2.0804P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6573
_refine_ls_number_parameters     542
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_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 0.7888(2) 0.53242(14) 0.67736(9) 0.0238(3) Uani 1 1 d . . .
O2 O 0.5497(2) 0.63695(14) 0.91186(9) 0.0250(4) Uani 1 1 d . . .
O3 O 1.0290(3) 0.11749(16) 0.41058(9) 0.0338(4) Uani 1 1 d . . .
H1O3 H 0.952(5) 0.153(3) 0.4401(18) 0.048(9) Uiso 1 1 d . . .
O4 O 1.0290(2) 0.10069(14) 0.14429(9) 0.0259(4) Uani 1 1 d . . .
O5 O 0.1953(2) 0.34698(15) 0.61288(9) 0.0261(4) Uani 1 1 d . . .
H105 H 0.269(5) 0.317(3) 0.5801(19) 0.054(10) Uiso 1 1 d . . .
O6 O 0.1526(2) 0.24624(15) 0.88822(9) 0.0263(4) Uani 1 1 d . . .
N1 N 0.7499(3) 0.28735(17) 0.44686(10) 0.0222(4) Uani 1 1 d . . .
N2 N 0.4618(3) 0.19027(17) 0.56000(10) 0.0217(4) Uani 1 1 d . . .
N3 N 0.6523(3) 0.35681(17) 0.63945(10) 0.0213(4) Uani 1 1 d . . .
H1N3 H 0.524(4) 0.381(2) 0.6276(15) 0.029(7) Uiso 1 1 d . . .
C1 C 0.7349(3) 0.2781(2) 0.58954(12) 0.0213(5) Uani 1 1 d . . .
H1 H 0.870(4) 0.251(2) 0.6058(15) 0.028(7) Uiso 1 1 d . . .
C2 C 0.7311(4) 0.3532(2) 0.50786(13) 0.0272(5) Uani 1 1 d . . .
H2B H 0.832(4) 0.396(2) 0.5041(14) 0.027(7) Uiso 1 1 d . . .
H2A H 0.606(4) 0.413(3) 0.5007(16) 0.040(8) Uiso 1 1 d . . .
C3 C 0.5636(3) 0.2680(2) 0.42599(13) 0.0265(5) Uani 1 1 d . . .
H3B H 0.476(4) 0.343(2) 0.4186(15) 0.033(7) Uiso 1 1 d . . .
H3A H 0.575(4) 0.246(2) 0.3750(16) 0.032(7) Uiso 1 1 d . . .
C4 C 0.4863(4) 0.1714(2) 0.48107(13) 0.0261(5) Uani 1 1 d . . .
H4B H 0.569(4) 0.094(2) 0.4814(15) 0.031(7) Uiso 1 1 d . . .
H4A H 0.357(4) 0.171(2) 0.4592(16) 0.039(8) Uiso 1 1 d . . .
C5 C 0.6477(3) 0.1692(2) 0.59749(13) 0.0211(4) Uani 1 1 d . . .
H5B H 0.636(3) 0.135(2) 0.6540(14) 0.022(6) Uiso 1 1 d . . .
H5A H 0.734(4) 0.110(2) 0.5777(16) 0.035(8) Uiso 1 1 d . . .
C6 C 0.6729(3) 0.3076(2) 0.72239(12) 0.0212(4) Uani 1 1 d . . .
H6B H 0.807(3) 0.271(2) 0.7303(13) 0.016(6) Uiso 1 1 d . . .
H6A H 0.588(4) 0.247(2) 0.7415(14) 0.024(6) Uiso 1 1 d . . .
C7 C 0.6306(3) 0.40081(19) 0.76848(12) 0.0190(4) Uani 1 1 d . . .
C8 C 0.5426(3) 0.3790(2) 0.83996(12) 0.0205(4) Uani 1 1 d . . .
H8 H 0.496(4) 0.306(2) 0.8563(15) 0.028(7) Uiso 1 1 d . . .
C9 C 0.5189(3) 0.4581(2) 0.88711(12) 0.0211(4) Uani 1 1 d . . .
H9 H 0.457(4) 0.441(2) 0.9385(15) 0.027(7) Uiso 1 1 d . . .
C10 C 0.5820(3) 0.56348(19) 0.86214(12) 0.0205(4) Uani 1 1 d . . .
C11 C 0.6692(3) 0.5891(2) 0.79093(12) 0.0205(4) Uani 1 1 d . . .
H11 H 0.720(4) 0.658(2) 0.7735(14) 0.025(7) Uiso 1 1 d . . .
C12 C 0.6947(3) 0.5069(2) 0.74511(12) 0.0200(4) Uani 1 1 d . . .
C13 C 0.5767(4) 0.7550(2) 0.88477(13) 0.0243(5) Uani 1 1 d . . .
H13B H 0.714(4) 0.755(2) 0.8764(14) 0.025(7) Uiso 1 1 d . . .
H13A H 0.512(4) 0.789(2) 0.8349(15) 0.025(7) Uiso 1 1 d . . .
C14 C 0.5012(4) 0.8191(2) 0.94609(15) 0.0295(5) Uani 1 1 d . . .
H14C H 0.367(4) 0.814(2) 0.9535(16) 0.038(8) Uiso 1 1 d . . .
H14B H 0.520(4) 0.902(3) 0.9309(16) 0.040(8) Uiso 1 1 d . . .
H14A H 0.563(4) 0.784(3) 0.9958(18) 0.047(9) Uiso 1 1 d . . .
C15 C 0.8348(4) 0.3540(2) 0.37778(13) 0.0258(5) Uani 1 1 d . . .
H15B H 0.954(4) 0.374(2) 0.3961(14) 0.023(6) Uiso 1 1 d . . .
H15A H 0.747(4) 0.428(2) 0.3562(14) 0.022(6) Uiso 1 1 d . . .
C16 C 0.8821(3) 0.2841(2) 0.31716(12) 0.0216(5) Uani 1 1 d . . .
C17 C 0.8326(3) 0.3307(2) 0.24069(13) 0.0223(5) Uani 1 1 d . . .
H17 H 0.760(4) 0.408(2) 0.2278(14) 0.026(7) Uiso 1 1 d . . .
C18 C 0.8823(3) 0.2691(2) 0.18364(12) 0.0224(5) Uani 1 1 d . . .
H18 H 0.849(4) 0.303(2) 0.1304(15) 0.025(7) Uiso 1 1 d . . .
C19 C 0.9850(3) 0.1568(2) 0.20362(12) 0.0220(5) Uani 1 1 d . . .
C20 C 1.0358(3) 0.1068(2) 0.27969(13) 0.0250(5) Uani 1 1 d . . .
H20 H 1.097(4) 0.029(2) 0.2941(14) 0.024(6) Uiso 1 1 d . . .
C21 C 0.9818(3) 0.1706(2) 0.33577(12) 0.0235(5) Uani 1 1 d . . .
C22 C 1.1532(4) -0.0086(2) 0.16013(14) 0.0283(5) Uani 1 1 d . . .
H22B H 1.097(4) -0.065(2) 0.2017(15) 0.025(7) Uiso 1 1 d . . .
H22A H 1.274(4) 0.001(2) 0.1824(16) 0.034(7) Uiso 1 1 d . . .
C23 C 1.1808(4) -0.0509(3) 0.08575(16) 0.0358(6) Uani 1 1 d . . .
H23C H 1.059(4) -0.067(3) 0.0693(17) 0.042(8) Uiso 1 1 d . . .
H23B H 1.225(5) 0.013(3) 0.0426(19) 0.057(10) Uiso 1 1 d . . .
H23A H 1.277(5) -0.120(3) 0.0934(19) 0.056(10) Uiso 1 1 d . . .
C24 C 0.3398(4) 0.1127(2) 0.60558(14) 0.0275(5) Uani 1 1 d . . .
H24B H 0.404(4) 0.028(2) 0.6162(15) 0.032(7) Uiso 1 1 d . . .
H24A H 0.223(4) 0.122(2) 0.5734(15) 0.031(7) Uiso 1 1 d . . .
C25 C 0.2878(3) 0.1481(2) 0.68046(13) 0.0224(5) Uani 1 1 d . . .
C26 C 0.3133(4) 0.0695(2) 0.75095(14) 0.0279(5) Uani 1 1 d . . .
H26 H 0.365(4) -0.013(3) 0.7521(16) 0.038(8) Uiso 1 1 d . . .
C27 C 0.2670(3) 0.1043(2) 0.81936(14) 0.0279(5) Uani 1 1 d . . .
H27 H 0.281(4) 0.050(2) 0.8694(16) 0.036(8) Uiso 1 1 d . . .
C28 C 0.1922(3) 0.2207(2) 0.81799(12) 0.0224(5) Uani 1 1 d . . .
C29 C 0.1666(3) 0.3021(2) 0.74843(12) 0.0203(4) Uani 1 1 d . . .
H29 H 0.122(4) 0.380(2) 0.7475(14) 0.026(7) Uiso 1 1 d . . .
C30 C 0.2163(3) 0.2649(2) 0.68071(12) 0.0206(4) Uani 1 1 d . . .
C31 C 0.0440(3) 0.3586(2) 0.89111(13) 0.0247(5) Uani 1 1 d . . .
H31B H -0.070(4) 0.375(2) 0.8590(14) 0.022(6) Uiso 1 1 d . . .
H31A H 0.120(4) 0.422(2) 0.8706(14) 0.024(6) Uiso 1 1 d . . .
C32 C -0.0097(4) 0.3549(3) 0.97383(15) 0.0357(6) Uani 1 1 d . . .
H32C H -0.092(4) 0.426(3) 0.9768(17) 0.043(8) Uiso 1 1 d . . .
H32B H 0.104(5) 0.348(3) 1.0052(18) 0.050(9) Uiso 1 1 d . . .
H32A H -0.070(5) 0.284(3) 0.9951(19) 0.060(10) Uiso 1 1 d . . .
H1O1 H 0.760(5) 0.480(3) 0.6515(19) 0.053(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 C12 1.367(3) . ?
O1 H1O1 0.91(3) . ?
O2 C10 1.369(3) . ?
O2 C13 1.433(3) . ?
O3 C21 1.375(3) . ?
O3 H1O3 0.87(3) . ?
O4 C19 1.375(3) . ?
O4 C22 1.423(3) . ?
O5 C30 1.375(3) . ?
O5 H105 0.87(3) . ?
O6 C28 1.365(3) . ?
O6 C31 1.439(3) . ?
N1 C2 1.469(3) . ?
N1 C3 1.482(3) . ?
N1 C15 1.489(3) . ?
N2 C4 1.477(3) . ?
N2 C5 1.480(3) . ?
N2 C24 1.485(3) . ?
N3 C1 1.471(3) . ?
N3 C6 1.472(3) . ?
N3 H1N3 0.94(3) . ?
C1 C5 1.523(3) . ?
C1 C2 1.534(3) . ?
C1 H1 1.00(3) . ?
C2 H2B 0.96(3) . ?
C2 H2A 1.04(3) . ?
C3 C4 1.516(3) . ?
C3 H3B 0.99(3) . ?
C3 H3A 1.00(3) . ?
C4 H4B 1.01(3) . ?
C4 H4A 1.03(3) . ?
C5 H5B 1.01(2) . ?
C5 H5A 0.98(3) . ?
C6 C7 1.510(3) . ?
C6 H6B 0.99(2) . ?
C6 H6A 1.02(3) . ?
C7 C8 1.398(3) . ?
C7 C12 1.400(3) . ?
C8 C9 1.385(3) . ?
C8 H8 0.97(3) . ?
C9 C10 1.392(3) . ?
C9 H9 1.00(3) . ?
C10 C11 1.394(3) . ?
C11 C12 1.397(3) . ?
C11 H11 0.94(3) . ?
C13 C14 1.504(3) . ?
C13 H13B 1.00(3) . ?
C13 H13A 0.99(3) . ?
C14 H14C 0.98(3) . ?
C14 H14B 1.00(3) . ?
C14 H14A 0.98(3) . ?
C15 C16 1.503(3) . ?
C15 H15B 1.01(3) . ?
C15 H15A 1.00(3) . ?
C16 C21 1.392(3) . ?
C16 C17 1.392(3) . ?
C17 C18 1.386(3) . ?
C17 H17 0.96(3) . ?
C18 C19 1.389(3) . ?
C18 H18 0.97(3) . ?
C19 C20 1.394(3) . ?
C20 C21 1.393(3) . ?
C20 H20 0.94(3) . ?
C22 C23 1.519(3) . ?
C22 H22B 1.02(3) . ?
C22 H22A 1.01(3) . ?
C23 H23C 1.01(3) . ?
C23 H23B 1.04(3) . ?
C23 H23A 0.97(4) . ?
C24 C25 1.506(3) . ?
C24 H24B 1.02(3) . ?
C24 H24A 1.01(3) . ?
C25 C26 1.392(3) . ?
C25 C30 1.399(3) . ?
C26 C27 1.388(3) . ?
C26 H26 0.98(3) . ?
C27 C28 1.394(3) . ?
C27 H27 0.98(3) . ?
C28 C29 1.394(3) . ?
C29 C30 1.393(3) . ?
C29 H29 0.92(3) . ?
C31 C32 1.507(3) . ?
C31 H31B 0.99(3) . ?
C31 H31A 1.01(3) . ?
C32 H32C 0.96(3) . ?
C32 H32B 1.00(3) . ?
C32 H32A 1.01(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
C12 O1 H1O1 103(2) . . ?
C10 O2 C13 118.33(17) . . ?
C21 O3 H1O3 108(2) . . ?
C19 O4 C22 117.69(18) . . ?
C30 O5 H105 106(2) . . ?
C28 O6 C31 118.09(17) . . ?
C2 N1 C3 110.74(19) . . ?
C2 N1 C15 109.37(18) . . ?
C3 N1 C15 108.86(18) . . ?
C4 N2 C5 109.82(18) . . ?
C4 N2 C24 110.97(17) . . ?
C5 N2 C24 109.99(18) . . ?
C1 N3 C6 115.50(18) . . ?
C1 N3 H1N3 108.5(16) . . ?
C6 N3 H1N3 109.1(16) . . ?
N3 C1 C5 114.93(18) . . ?
N3 C1 C2 106.41(18) . . ?
C5 C1 C2 114.45(18) . . ?
N3 C1 H1 105.6(15) . . ?
C5 C1 H1 107.0(15) . . ?
C2 C1 H1 108.0(15) . . ?
N1 C2 C1 114.68(19) . . ?
N1 C2 H2B 109.5(15) . . ?
C1 C2 H2B 107.1(16) . . ?
N1 C2 H2A 109.4(16) . . ?
C1 C2 H2A 108.2(16) . . ?
H2B C2 H2A 108(2) . . ?
N1 C3 C4 115.14(19) . . ?
N1 C3 H3B 108.0(16) . . ?
C4 C3 H3B 112.1(16) . . ?
N1 C3 H3A 108.4(16) . . ?
C4 C3 H3A 106.6(16) . . ?
H3B C3 H3A 106(2) . . ?
N2 C4 C3 113.45(19) . . ?
N2 C4 H4B 110.0(15) . . ?
C3 C4 H4B 110.5(15) . . ?
N2 C4 H4A 109.2(16) . . ?
C3 C4 H4A 105.2(16) . . ?
H4B C4 H4A 108(2) . . ?
N2 C5 C1 114.10(19) . . ?
N2 C5 H5B 109.9(14) . . ?
C1 C5 H5B 107.5(14) . . ?
N2 C5 H5A 110.0(17) . . ?
C1 C5 H5A 109.7(17) . . ?
H5B C5 H5A 105(2) . . ?
N3 C6 C7 111.89(19) . . ?
N3 C6 H6B 105.7(13) . . ?
C7 C6 H6B 108.1(13) . . ?
N3 C6 H6A 112.2(14) . . ?
C7 C6 H6A 108.5(14) . . ?
H6B C6 H6A 110.5(19) . . ?
C8 C7 C12 117.6(2) . . ?
C8 C7 C6 120.6(2) . . ?
C12 C7 C6 121.41(19) . . ?
C9 C8 C7 122.1(2) . . ?
C9 C8 H8 119.7(15) . . ?
C7 C8 H8 118.2(15) . . ?
C8 C9 C10 119.1(2) . . ?
C8 C9 H9 121.1(15) . . ?
C10 C9 H9 119.8(15) . . ?
O2 C10 C9 115.01(19) . . ?
O2 C10 C11 124.3(2) . . ?
C9 C10 C11 120.6(2) . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 H11 122.8(15) . . ?
C12 C11 H11 117.9(15) . . ?
O1 C12 C11 117.63(19) . . ?
O1 C12 C7 120.98(19) . . ?
C11 C12 C7 121.4(2) . . ?
O2 C13 C14 106.52(19) . . ?
O2 C13 H13B 108.4(15) . . ?
C14 C13 H13B 111.3(15) . . ?
O2 C13 H13A 109.9(15) . . ?
C14 C13 H13A 112.5(15) . . ?
H13B C13 H13A 108(2) . . ?
C13 C14 H14C 108.4(17) . . ?
C13 C14 H14B 110.0(17) . . ?
H14C C14 H14B 111(2) . . ?
C13 C14 H14A 112.5(18) . . ?
H14C C14 H14A 107(2) . . ?
H14B C14 H14A 108(2) . . ?
N1 C15 C16 111.83(19) . . ?
N1 C15 H15B 106.1(14) . . ?
C16 C15 H15B 110.1(14) . . ?
N1 C15 H15A 110.2(14) . . ?
C16 C15 H15A 109.8(14) . . ?
H15B C15 H15A 109(2) . . ?
C21 C16 C17 117.7(2) . . ?
C21 C16 C15 120.6(2) . . ?
C17 C16 C15 121.7(2) . . ?
C18 C17 C16 122.3(2) . . ?
C18 C17 H17 119.6(15) . . ?
C16 C17 H17 118.1(15) . . ?
C17 C18 C19 118.7(2) . . ?
C17 C18 H18 121.8(15) . . ?
C19 C18 H18 119.5(15) . . ?
O4 C19 C18 115.66(19) . . ?
O4 C19 C20 123.8(2) . . ?
C18 C19 C20 120.6(2) . . ?
C21 C20 C19 119.3(2) . . ?
C21 C20 H20 119.6(15) . . ?
C19 C20 H20 120.9(15) . . ?
O3 C21 C16 120.8(2) . . ?
O3 C21 C20 117.8(2) . . ?
C16 C21 C20 121.4(2) . . ?
O4 C22 C23 107.3(2) . . ?
O4 C22 H22B 109.6(15) . . ?
C23 C22 H22B 111.7(14) . . ?
O4 C22 H22A 109.6(16) . . ?
C23 C22 H22A 113.4(16) . . ?
H22B C22 H22A 105(2) . . ?
C22 C23 H23C 110.0(17) . . ?
C22 C23 H23B 109.7(18) . . ?
H23C C23 H23B 108(2) . . ?
C22 C23 H23A 109(2) . . ?
H23C C23 H23A 111(3) . . ?
H23B C23 H23A 109(3) . . ?
N2 C24 C25 110.01(18) . . ?
N2 C24 H24B 111.8(15) . . ?
C25 C24 H24B 109.4(15) . . ?
N2 C24 H24A 106.4(15) . . ?
C25 C24 H24A 110.7(15) . . ?
H24B C24 H24A 109(2) . . ?
C26 C25 C30 117.7(2) . . ?
C26 C25 C24 122.6(2) . . ?
C30 C25 C24 119.7(2) . . ?
C27 C26 C25 121.6(2) . . ?
C27 C26 H26 119.4(17) . . ?
C25 C26 H26 118.9(17) . . ?
C26 C27 C28 119.6(2) . . ?
C26 C27 H27 122.9(17) . . ?
C28 C27 H27 117.5(16) . . ?
O6 C28 C27 115.1(2) . . ?
O6 C28 C29 124.6(2) . . ?
C27 C28 C29 120.3(2) . . ?
C30 C29 C28 118.9(2) . . ?
C30 C29 H29 120.7(16) . . ?
C28 C29 H29 120.4(16) . . ?
O5 C30 C29 118.0(2) . . ?
O5 C30 C25 120.09(19) . . ?
C29 C30 C25 121.9(2) . . ?
O6 C31 C32 106.8(2) . . ?
O6 C31 H31B 110.3(14) . . ?
C32 C31 H31B 110.4(14) . . ?
O6 C31 H31A 110.5(15) . . ?
C32 C31 H31A 111.3(14) . . ?
H31B C31 H31A 108(2) . . ?
C31 C32 H32C 108.5(18) . . ?
C31 C32 H32B 110.4(19) . . ?
H32C C32 H32B 109(3) . . ?
C31 C32 H32A 110.0(19) . . ?
H32C C32 H32A 112(3) . . ?
H32B C32 H32A 107(3) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.057
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FO6293
_database_code_depnum_ccdc_archive 'CCDC 1820197'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H37 N3 O6'
_chemical_formula_sum            'C29 H37 N3 O6'
_chemical_formula_weight         523.62

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   14.0088(5)
_cell_length_b                   5.7639(2)
_cell_length_c                   33.2059(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.854(2)
_cell_angle_gamma                90
_cell_volume                     2649.27(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    24731
_cell_measurement_theta_min      2.07
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.066
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6511
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24731
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0541
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6023
_reflns_number_gt                4444
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_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)+(0.0379P)²+6.0070P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6023
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0805
_refine_ls_wR_factor_ref         0.1836
_refine_ls_wR_factor_gt          0.1635
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.005
_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 0.16154(17) 0.2173(4) 0.83269(6) 0.0308(5) Uani 1 1 d . . .
O2 O 0.07206(14) 0.4546(4) 0.96083(6) 0.0283(4) Uani 1 1 d . . .
O3 O 0.19406(16) 0.7952(3) 0.65483(6) 0.0316(5) Uani 1 1 d . . .
O4 O 0.25919(15) 0.5287(4) 0.52458(6) 0.0325(5) Uani 1 1 d . . .
O5 O 0.53367(18) 0.6466(5) 0.68451(7) 0.0487(7) Uani 1 1 d . . .
O6 O 0.58068(16) 0.5801(5) 0.54475(7) 0.0438(6) Uani 1 1 d . . .
N1 N 0.23774(16) 0.5414(4) 0.78829(6) 0.0233(5) Uani 1 1 d . . .
N2 N 0.13998(16) 0.4610(4) 0.70251(7) 0.0224(5) Uani 1 1 d . . .
N3 N 0.36979(18) 0.4404(5) 0.69990(8) 0.0316(6) Uani 1 1 d . . .
C1 C 0.3111(2) 0.5679(5) 0.76112(8) 0.0282(6) Uani 1 1 d . . .
H1A H 0.3755 0.5827 0.7780 0.034 Uiso 1 1 calc R . .
H1B H 0.2981 0.7131 0.7453 0.034 Uiso 1 1 calc R . .
C2 C 0.3133(2) 0.3645(5) 0.73131(8) 0.0278(6) Uani 1 1 d . . .
H2A H 0.3490 0.2338 0.7467 0.033 Uiso 1 1 calc R . .
C3 C 0.21280(19) 0.2757(5) 0.71350(8) 0.0252(6) Uani 1 1 d . . .
H3A H 0.2180 0.1830 0.6888 0.030 Uiso 1 1 calc R . .
H3B H 0.1897 0.1711 0.7336 0.030 Uiso 1 1 calc R . .
C4 C 0.0871(2) 0.5096(5) 0.73656(8) 0.0264(6) Uani 1 1 d . . .
H4A H 0.0676 0.3606 0.7477 0.032 Uiso 1 1 calc R . .
H4B H 0.0274 0.5962 0.7260 0.032 Uiso 1 1 calc R . .
C5 C 0.1449(2) 0.6486(5) 0.77088(8) 0.0257(6) Uani 1 1 d . . .
H5A H 0.1577 0.8047 0.7605 0.031 Uiso 1 1 calc R . .
H5B H 0.1053 0.6690 0.7929 0.031 Uiso 1 1 calc R . .
C6 C 0.2746(2) 0.6475(5) 0.82872(8) 0.0271(6) Uani 1 1 d . . .
H6A H 0.2772 0.8180 0.8255 0.032 Uiso 1 1 calc R . .
H6B H 0.3413 0.5921 0.8379 0.032 Uiso 1 1 calc R . .
C7 C 0.21361(19) 0.5920(5) 0.86128(8) 0.0236(6) Uani 1 1 d . . .
C8 C 0.2118(2) 0.7477(5) 0.89339(8) 0.0263(6) Uani 1 1 d . . .
H8A H 0.2440 0.8924 0.8927 0.032 Uiso 1 1 calc R . .
C9 C 0.1649(2) 0.6992(5) 0.92617(9) 0.0282(6) Uani 1 1 d . . .
H9A H 0.1658 0.8079 0.9477 0.034 Uiso 1 1 calc R . .
C10 C 0.11621(19) 0.4889(5) 0.92712(8) 0.0237(6) Uani 1 1 d . . .
C11 C 0.1136(2) 0.3307(5) 0.89514(8) 0.0237(6) Uani 1 1 d . . .
H11A H 0.0785 0.1899 0.8953 0.028 Uiso 1 1 calc R . .
C12 C 0.1636(2) 0.3823(5) 0.86281(8) 0.0233(6) Uani 1 1 d . . .
C13 C 0.0204(2) 0.2423(5) 0.96350(9) 0.0298(6) Uani 1 1 d . . .
H13A H -0.0108 0.2447 0.9880 0.045 Uiso 1 1 calc R . .
H13B H 0.0655 0.1114 0.9651 0.045 Uiso 1 1 calc R . .
H13C H -0.0288 0.2253 0.9393 0.045 Uiso 1 1 calc R . .
C14 C 0.0738(2) 0.4005(5) 0.66406(8) 0.0259(6) Uani 1 1 d . . .
H14A H 0.0163 0.5024 0.6610 0.031 Uiso 1 1 calc R . .
H14B H 0.0518 0.2378 0.6654 0.031 Uiso 1 1 calc R . .
C15 C 0.12647(19) 0.4303(5) 0.62781(8) 0.0231(6) Uani 1 1 d . . .
C16 C 0.1196(2) 0.2685(5) 0.59622(8) 0.0253(6) Uani 1 1 d . . .
H16A H 0.0835 0.1305 0.5981 0.030 Uiso 1 1 calc R . .
C17 C 0.1641(2) 0.3042(5) 0.56223(8) 0.0266(6) Uani 1 1 d . . .
H17A H 0.1578 0.1923 0.5410 0.032 Uiso 1 1 calc R . .
C18 C 0.2182(2) 0.5052(5) 0.55939(8) 0.0262(6) Uani 1 1 d . . .
C19 C 0.2284(2) 0.6681(5) 0.59068(8) 0.0258(6) Uani 1 1 d . . .
H19A H 0.2662 0.8035 0.5891 0.031 Uiso 1 1 calc R . .
C20 C 0.1822(2) 0.6301(5) 0.62449(8) 0.0246(6) Uani 1 1 d . . .
C21 C 0.3170(2) 0.7320(6) 0.52157(10) 0.0375(7) Uani 1 1 d . . .
H21A H 0.3454 0.7250 0.4964 0.056 Uiso 1 1 calc R . .
H21B H 0.3686 0.7390 0.5451 0.056 Uiso 1 1 calc R . .
H21C H 0.2763 0.8706 0.5212 0.056 Uiso 1 1 calc R . .
C22 C 0.4068(2) 0.2474(6) 0.67710(10) 0.0382(7) Uani 1 1 d . . .
H22A H 0.3527 0.1436 0.6661 0.046 Uiso 1 1 calc R . .
H22B H 0.4542 0.1556 0.6958 0.046 Uiso 1 1 calc R . .
C23 C 0.4541(2) 0.3396(6) 0.64268(10) 0.0337(7) Uani 1 1 d . . .
C24 C 0.4392(2) 0.2363(6) 0.60417(11) 0.0409(8) Uani 1 1 d . . .
H24A H 0.3977 0.1053 0.5998 0.049 Uiso 1 1 calc R . .
C25 C 0.4821(2) 0.3166(6) 0.57244(11) 0.0423(8) Uani 1 1 d . . .
H25A H 0.4707 0.2400 0.5468 0.051 Uiso 1 1 calc R . .
C26 C 0.5423(2) 0.5101(6) 0.57763(9) 0.0331(7) Uani 1 1 d . . .
C27 C 0.5584(2) 0.6209(6) 0.61575(9) 0.0337(7) Uani 1 1 d . . .
H27A H 0.5984 0.7547 0.6197 0.040 Uiso 1 1 calc R . .
C28 C 0.5156(2) 0.5339(6) 0.64760(9) 0.0326(7) Uani 1 1 d . . .
C29 C 0.6393(3) 0.7844(6) 0.54808(11) 0.0438(8) Uani 1 1 d . . .
H29A H 0.6620 0.8135 0.5221 0.066 Uiso 1 1 calc R . .
H29B H 0.6950 0.7625 0.5695 0.066 Uiso 1 1 calc R . .
H29C H 0.6012 0.9172 0.5549 0.066 Uiso 1 1 calc R . .
H1O1 H 0.195(3) 0.265(7) 0.8169(11) 0.046(11) Uiso 1 1 d . . .
H1O3 H 0.177(3) 0.728(7) 0.6773(12) 0.054(11) Uiso 1 1 d . . .
H1O5 H 0.516(2) 0.563(5) 0.7065(9) 0.020(7) Uiso 1 1 d . . .
H1N3 H 0.326(3) 0.549(7) 0.6823(11) 0.050(11) 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 C12 1.377(3) . ?
O1 H1O1 0.80(4) . ?
O2 C10 1.374(3) . ?
O2 C13 1.431(3) . ?
O3 C20 1.378(3) . ?
O3 H1O3 0.91(4) . ?
O4 C18 1.374(3) . ?
O4 C21 1.436(4) . ?
O5 C28 1.376(4) . ?
O5 H1O5 0.94(3) . ?
O6 C26 1.351(4) . ?
O6 C29 1.430(4) . ?
N1 C5 1.475(3) . ?
N1 C1 1.476(3) . ?
N1 C6 1.493(3) . ?
N2 C4 1.471(3) . ?
N2 C3 1.483(3) . ?
N2 C14 1.499(3) . ?
N3 C2 1.470(4) . ?
N3 C22 1.484(4) . ?
N3 H1N3 1.00(4) . ?
C1 C2 1.537(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.528(4) . ?
C2 H2A 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.521(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.511(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.397(4) . ?
C7 C12 1.402(4) . ?
C8 C9 1.384(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.393(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.396(4) . ?
C11 C12 1.401(4) . ?
C11 H11A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.515(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.396(4) . ?
C15 C20 1.405(4) . ?
C16 C17 1.386(4) . ?
C16 H16A 0.9500 . ?
C17 C18 1.396(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.391(4) . ?
C19 C20 1.396(4) . ?
C19 H19A 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.504(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.397(4) . ?
C23 C28 1.407(4) . ?
C24 C25 1.372(5) . ?
C24 H24A 0.9500 . ?
C25 C26 1.393(5) . ?
C25 H25A 0.9500 . ?
C26 C27 1.405(4) . ?
C27 C28 1.388(4) . ?
C27 H27A 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
C12 O1 H1O1 107(3) . . ?
C10 O2 C13 118.0(2) . . ?
C20 O3 H1O3 107(3) . . ?
C18 O4 C21 116.9(2) . . ?
C28 O5 H1O5 114.6(18) . . ?
C26 O6 C29 118.6(3) . . ?
C5 N1 C1 111.8(2) . . ?
C5 N1 C6 110.0(2) . . ?
C1 N1 C6 109.3(2) . . ?
C4 N2 C3 110.9(2) . . ?
C4 N2 C14 112.4(2) . . ?
C3 N2 C14 110.7(2) . . ?
C2 N3 C22 114.0(2) . . ?
C2 N3 H1N3 105(2) . . ?
C22 N3 H1N3 114(2) . . ?
N1 C1 C2 113.5(2) . . ?
N1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
N3 C2 C3 112.9(2) . . ?
N3 C2 C1 107.2(2) . . ?
C3 C2 C1 113.4(2) . . ?
N3 C2 H2A 107.7 . . ?
C3 C2 H2A 107.7 . . ?
C1 C2 H2A 107.7 . . ?
N2 C3 C2 114.3(2) . . ?
N2 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
N2 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N2 C4 C5 113.8(2) . . ?
N2 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
N2 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
N1 C5 C4 114.1(2) . . ?
N1 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
N1 C6 C7 113.7(2) . . ?
N1 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
N1 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C12 117.3(2) . . ?
C8 C7 C6 119.3(2) . . ?
C12 C7 C6 123.3(2) . . ?
C9 C8 C7 122.5(3) . . ?
C9 C8 H8A 118.7 . . ?
C7 C8 H8A 118.7 . . ?
C8 C9 C10 119.1(3) . . ?
C8 C9 H9A 120.4 . . ?
C10 C9 H9A 120.4 . . ?
O2 C10 C9 115.3(2) . . ?
O2 C10 C11 124.3(3) . . ?
C9 C10 C11 120.4(2) . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 H11A 120.4 . . ?
C12 C11 H11A 120.4 . . ?
O1 C12 C11 117.0(2) . . ?
O1 C12 C7 121.6(2) . . ?
C11 C12 C7 121.5(2) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 109.7(2) . . ?
N2 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
N2 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C20 117.6(2) . . ?
C16 C15 C14 122.4(3) . . ?
C20 C15 C14 120.0(2) . . ?
C17 C16 C15 121.7(3) . . ?
C17 C16 H16A 119.2 . . ?
C15 C16 H16A 119.2 . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17A 120.2 . . ?
C18 C17 H17A 120.2 . . ?
O4 C18 C19 123.6(3) . . ?
O4 C18 C17 116.1(3) . . ?
C19 C18 C17 120.2(3) . . ?
C18 C19 C20 119.2(3) . . ?
C18 C19 H19A 120.4 . . ?
C20 C19 H19A 120.4 . . ?
O3 C20 C19 117.5(2) . . ?
O3 C20 C15 121.0(2) . . ?
C19 C20 C15 121.6(3) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 C23 110.6(3) . . ?
N3 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C24 C23 C28 116.6(3) . . ?
C24 C23 C22 121.6(3) . . ?
C28 C23 C22 121.8(3) . . ?
C25 C24 C23 122.6(3) . . ?
C25 C24 H24A 118.7 . . ?
C23 C24 H24A 118.7 . . ?
C24 C25 C26 120.3(3) . . ?
C24 C25 H25A 119.9 . . ?
C26 C25 H25A 119.9 . . ?
O6 C26 C25 116.6(3) . . ?
O6 C26 C27 124.3(3) . . ?
C25 C26 C27 119.1(3) . . ?
C28 C27 C26 119.6(3) . . ?
C28 C27 H27A 120.2 . . ?
C26 C27 H27A 120.2 . . ?
O5 C28 C27 117.8(3) . . ?
O5 C28 C23 120.3(3) . . ?
C27 C28 C23 121.9(3) . . ?
O6 C29 H29A 109.5 . . ?
O6 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O6 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.064
