# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_cdc
_database_code_depnum_ccdc_archive 'CCDC 1045629'
_audit_update_record             
;
2015-01-26 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H31 N3 O3'
_chemical_formula_weight         469.57

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   C2/c

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

_cell_length_a                   28.938(6)
_cell_length_b                   11.193(2)
_cell_length_c                   16.370(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.12(3)
_cell_angle_gamma                90.00
_cell_volume                     5039.1(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    173
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.085
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            yellowish
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2000
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5859
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298-300
_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32801
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4946
_reflns_number_gt                3418
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0812P)²+1.3974P] 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_number_reflns         4946
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.05613(5) 0.56345(12) 0.46887(9) 0.0455(4) Uani 1 1 d . . .
O1 O 0.14698(5) 0.23393(12) 0.48174(9) 0.0453(4) Uani 1 1 d . . .
N1 N 0.16797(5) 0.48991(13) 0.43715(9) 0.0314(4) Uani 1 1 d . . .
N2 N 0.08852(5) 0.38021(14) 0.46224(9) 0.0340(4) Uani 1 1 d . . .
C11 C 0.18929(7) 0.57209(17) 0.31267(11) 0.0349(4) Uani 1 1 d . . .
H3A H 0.1636 0.6259 0.3014 0.042 Uiso 1 1 calc R . .
O3 O 0.28479(5) 0.50029(13) 0.22057(8) 0.0450(4) Uani 1 1 d . . .
C15 C 0.23680(7) 0.41485(17) 0.39676(12) 0.0359(4) Uani 1 1 d . . .
H5A H 0.2430 0.3616 0.4425 0.043 Uiso 1 1 calc R . .
C12 C 0.21855(7) 0.56988(18) 0.25989(12) 0.0375(5) Uani 1 1 d . . .
H6A H 0.2121 0.6216 0.2132 0.045 Uiso 1 1 calc R . .
C7 C 0.09636(7) 0.77595(16) 0.39777(12) 0.0344(4) Uani 1 1 d . . .
H7A H 0.0685 0.7529 0.3544 0.041 Uiso 1 1 calc R . .
C14 C 0.26643(7) 0.41307(17) 0.34417(12) 0.0377(5) Uani 1 1 d . . .
H8A H 0.2922 0.3594 0.3550 0.045 Uiso 1 1 calc R . .
C8 C 0.13077(7) 0.69028(16) 0.43847(11) 0.0314(4) Uani 1 1 d . . .
C9 C 0.12310(6) 0.55993(16) 0.41199(11) 0.0307(4) Uani 1 1 d . . .
H10A H 0.1097 0.5571 0.3492 0.037 Uiso 1 1 calc R . .
C3 C 0.17233(7) 0.72443(17) 0.50430(12) 0.0341(4) Uani 1 1 d . . .
C6 C 0.10325(7) 0.89570(17) 0.42142(12) 0.0398(5) Uani 1 1 d . . .
H12A H 0.0802 0.9524 0.3936 0.048 Uiso 1 1 calc R . .
C10 C 0.19801(6) 0.49450(15) 0.38254(11) 0.0312(4) Uani 1 1 d . . .
C16 C 0.08578(7) 0.50220(16) 0.44955(11) 0.0332(4) Uani 1 1 d . . .
C13 C 0.25739(7) 0.49141(17) 0.27583(12) 0.0361(5) Uani 1 1 d . . .
C17 C 0.11946(7) 0.30312(17) 0.43249(12) 0.0352(4) Uani 1 1 d . . .
C5 C 0.14438(8) 0.92991(18) 0.48622(13) 0.0435(5) Uani 1 1 d . . .
H17A H 0.1492 1.0098 0.5023 0.052 Uiso 1 1 calc R . .
C18 C 0.10968(7) 0.29761(17) 0.33782(12) 0.0368(5) Uani 1 1 d . . .
C4 C 0.17840(7) 0.84484(18) 0.52718(12) 0.0396(5) Uani 1 1 d . . .
H19A H 0.2060 0.8685 0.5710 0.048 Uiso 1 1 calc R . .
C24 C 0.06008(7) 0.32956(17) 0.51596(11) 0.0349(4) Uani 1 1 d . . .
H20A H 0.0315 0.3809 0.5073 0.042 Uiso 1 1 calc R . .
C1 C 0.19354(7) 0.50607(17) 0.52996(11) 0.0354(4) Uani 1 1 d . . .
H21A H 0.2214 0.4531 0.5474 0.043 Uiso 1 1 calc R . .
H21B H 0.1719 0.4849 0.5625 0.043 Uiso 1 1 calc R . .
C19 C 0.06717(8) 0.34340(19) 0.28087(13) 0.0460(5) Uani 1 1 d . . .
H22A H 0.0445 0.3779 0.3034 0.055 Uiso 1 1 calc R . .
C29 C 0.04128(9) 0.20489(19) 0.48878(16) 0.0530(6) Uani 1 1 d . . .
H23A H 0.0683 0.1500 0.4974 0.064 Uiso 1 1 calc R . .
H23B H 0.0225 0.2044 0.4283 0.064 Uiso 1 1 calc R . .
C2 C 0.21045(7) 0.63460(17) 0.55001(12) 0.0391(5) Uani 1 1 d . . .
H24A H 0.2190 0.6476 0.6115 0.047 Uiso 1 1 calc R . .
H24B H 0.2395 0.6473 0.5334 0.047 Uiso 1 1 calc R . .
C23 C 0.14254(8) 0.24169(18) 0.30404(13) 0.0452(5) Uani 1 1 d . . .
H25A H 0.1706 0.2068 0.3403 0.054 Uiso 1 1 calc R . .
C28 C 0.00927(9) 0.1661(2) 0.54307(17) 0.0591(7) Uani 1 1 d . . .
H26A H -0.0189 0.2181 0.5309 0.071 Uiso 1 1 calc R . .
H26B H -0.0022 0.0853 0.5274 0.071 Uiso 1 1 calc R . .
N3 N 0.05695(8) 0.34065(19) 0.19488(12) 0.0619(6) Uani 1 1 d . . .
C22 C 0.13305(9) 0.2385(2) 0.21630(15) 0.0573(6) Uani 1 1 d . . .
H28A H 0.1548 0.2030 0.1922 0.069 Uiso 1 1 calc R . .
C21 C 0.09026(10) 0.2897(2) 0.16483(16) 0.0657(7) Uani 1 1 d . . .
H30A H 0.0843 0.2886 0.1056 0.079 Uiso 1 1 calc R . .
C26 C 0.05693(10) 0.2933(3) 0.66384(15) 0.0863(10) Uani 1 1 d . . .
H31A H 0.0760 0.2930 0.7242 0.104 Uiso 1 1 calc R . .
H31B H 0.0302 0.3488 0.6566 0.104 Uiso 1 1 calc R . .
C27 C 0.03691(10) 0.1707(3) 0.6384(2) 0.0819(10) Uani 1 1 d . . .
H32A H 0.0153 0.1492 0.6711 0.098 Uiso 1 1 calc R . .
H32B H 0.0633 0.1133 0.6517 0.098 Uiso 1 1 calc R . .
C25 C 0.08867(9) 0.3358(3) 0.61073(13) 0.0635(7) Uani 1 1 d . . .
H33A H 0.0991 0.4174 0.6263 0.076 Uiso 1 1 calc R . .
H33B H 0.1174 0.2859 0.6225 0.076 Uiso 1 1 calc R . .
C30 C 0.32572(9) 0.4233(2) 0.23588(17) 0.0640(7) Uani 1 1 d . . .
H10B H 0.3417 0.4376 0.1935 0.096 Uiso 1 1 calc R . .
H10C H 0.3151 0.3416 0.2324 0.096 Uiso 1 1 calc R . .
H10D H 0.3480 0.4386 0.2921 0.096 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
O2 C16 1.215(2) . ?
O1 C17 1.218(2) . ?
N1 C10 1.429(2) . ?
N1 C9 1.462(2) . ?
N1 C1 1.480(2) . ?
N2 C16 1.380(2) . ?
N2 C17 1.433(2) . ?
N2 C24 1.491(2) . ?
C11 C12 1.385(3) . ?
C11 C10 1.395(3) . ?
O3 C13 1.380(2) . ?
O3 C30 1.423(3) . ?
C15 C14 1.391(3) . ?
C15 C10 1.395(3) . ?
C12 C13 1.386(3) . ?
C7 C6 1.392(3) . ?
C7 C8 1.394(3) . ?
C14 C13 1.381(3) . ?
C8 C3 1.396(3) . ?
C8 C9 1.518(3) . ?
C9 C16 1.541(2) . ?
C3 C4 1.395(3) . ?
C3 C2 1.508(3) . ?
C6 C5 1.380(3) . ?
C17 C18 1.488(3) . ?
C5 C4 1.384(3) . ?
C18 C23 1.389(3) . ?
C18 C19 1.390(3) . ?
C24 C29 1.513(3) . ?
C24 C25 1.516(3) . ?
C1 C2 1.522(3) . ?
C19 N3 1.346(3) . ?
C29 C28 1.532(3) . ?
C23 C22 1.376(3) . ?
C28 C27 1.518(4) . ?
N3 C21 1.338(3) . ?
C22 C21 1.387(4) . ?
C26 C27 1.497(5) . ?
C26 C25 1.524(3) . ?

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
C10 N1 C9 117.67(14) . . ?
C10 N1 C1 115.52(14) . . ?
C9 N1 C1 109.90(14) . . ?
C16 N2 C17 123.87(15) . . ?
C16 N2 C24 116.66(15) . . ?
C17 N2 C24 119.30(15) . . ?
C12 C11 C10 120.69(18) . . ?
C13 O3 C30 117.23(16) . . ?
C14 C15 C10 121.63(17) . . ?
C11 C12 C13 120.74(18) . . ?
C6 C7 C8 120.69(18) . . ?
C13 C14 C15 119.62(18) . . ?
C7 C8 C3 119.78(17) . . ?
C7 C8 C9 120.36(16) . . ?
C3 C8 C9 119.86(16) . . ?
N1 C9 C8 113.37(15) . . ?
N1 C9 C16 109.52(14) . . ?
C8 C9 C16 110.31(14) . . ?
C4 C3 C8 118.56(18) . . ?
C4 C3 C2 119.96(17) . . ?
C8 C3 C2 121.48(17) . . ?
C5 C6 C7 119.71(19) . . ?
C15 C10 C11 117.75(17) . . ?
C15 C10 N1 119.15(16) . . ?
C11 C10 N1 123.04(16) . . ?
O2 C16 N2 122.11(17) . . ?
O2 C16 C9 120.45(16) . . ?
N2 C16 C9 117.42(15) . . ?
O3 C13 C14 125.04(18) . . ?
O3 C13 C12 115.39(17) . . ?
C14 C13 C12 119.56(17) . . ?
O1 C17 N2 120.45(16) . . ?
O1 C17 C18 122.43(17) . . ?
N2 C17 C18 116.26(16) . . ?
C6 C5 C4 119.69(19) . . ?
C23 C18 C19 118.16(18) . . ?
C23 C18 C17 120.10(18) . . ?
C19 C18 C17 121.70(17) . . ?
C5 C4 C3 121.57(19) . . ?
N2 C24 C29 113.02(15) . . ?
N2 C24 C25 111.12(15) . . ?
C29 C24 C25 112.06(18) . . ?
N1 C1 C2 111.19(15) . . ?
N3 C19 C18 123.6(2) . . ?
C24 C29 C28 108.52(17) . . ?
C3 C2 C1 112.76(16) . . ?
C22 C23 C18 119.2(2) . . ?
C27 C28 C29 111.5(2) . . ?
C21 N3 C19 116.4(2) . . ?
C23 C22 C21 118.3(2) . . ?
N3 C21 C22 124.2(2) . . ?
C27 C26 C25 112.2(3) . . ?
C26 C27 C28 110.6(2) . . ?
C24 C25 C26 109.59(18) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.055
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc and Hexane'
####################################################################### 
# 
# 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_27h
_database_code_depnum_ccdc_archive 'CCDC 1045630'
_audit_update_record             
;
2015-01-26 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          345-347
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H31 N3 O5'
_chemical_formula_weight         513.58

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.183(3)
_cell_length_b                   11.422(2)
_cell_length_c                   17.031(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.93(3)
_cell_angle_gamma                90.00
_cell_volume                     2559.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.41

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4981
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21638
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.99
_reflns_number_total             5018
_reflns_number_gt                2670
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5018
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1549
_refine_ls_R_factor_gt           0.0972
_refine_ls_wR_factor_ref         0.3344
_refine_ls_wR_factor_gt          0.2368
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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
C18 C 0.5408(3) -0.0384(3) 0.2511(2) 0.0389(9) Uani 1 1 d . . .
C20 C 0.6009(3) -0.0825(3) 0.1371(3) 0.0412(10) Uani 1 1 d . . .
H29A H 0.6055 -0.1607 0.1534 0.049 Uiso 1 1 calc R . .
C9 C 0.7820(3) 0.1651(3) 0.4367(3) 0.0428(10) Uani 1 1 d . . .
C25 C 0.4178(3) 0.0475(3) 0.3109(3) 0.0413(10) Uani 1 1 d . . .
C1 C 0.7002(3) 0.1138(3) 0.3582(3) 0.0410(10) Uani 1 1 d . . .
H16A H 0.6994 0.1610 0.3099 0.049 Uiso 1 1 calc R . .
N1 N 0.7225(3) -0.0062(3) 0.3417(2) 0.0418(8) Uani 1 1 d . . .
C19 C 0.5640(3) 0.0017(3) 0.1777(2) 0.0407(10) Uani 1 1 d . . .
C11 C 0.8081(3) -0.1372(3) 0.2770(3) 0.0460(10) Uani 1 1 d . . .
H35A H 0.7796 -0.2003 0.2947 0.055 Uiso 1 1 calc R . .
C2 C 0.7402(3) -0.0783(3) 0.4185(3) 0.0464(10) Uani 1 1 d . . .
H18A H 0.7439 -0.1603 0.4053 0.056 Uiso 1 1 calc R . .
H18B H 0.6839 -0.0684 0.4372 0.056 Uiso 1 1 calc R . .
C22 C 0.6214(3) 0.0665(4) 0.0434(3) 0.0468(10) Uani 1 1 d . . .
H27A H 0.6414 0.0870 -0.0009 0.056 Uiso 1 1 calc R . .
C12 C 0.8663(3) -0.1575(4) 0.2279(3) 0.0482(11) Uani 1 1 d . . .
H34A H 0.8763 -0.2336 0.2133 0.058 Uiso 1 1 calc R . .
N2 N 0.5196(3) 0.0503(3) 0.3041(2) 0.0419(8) Uani 1 1 d . . .
C24 C 0.5548(3) 0.1176(3) 0.1496(3) 0.0448(10) Uani 1 1 d . . .
H25A H 0.5303 0.1744 0.1763 0.054 Uiso 1 1 calc R . .
C10 C 0.7919(3) -0.0240(3) 0.2999(3) 0.0422(10) Uani 1 1 d . . .
C4 C 0.8498(3) 0.0909(4) 0.4969(3) 0.0470(10) Uani 1 1 d . . .
C13 C 0.9087(3) -0.0649(4) 0.2011(3) 0.0491(11) Uani 1 1 d . . .
C14 C 0.8951(4) 0.0474(4) 0.2264(3) 0.0528(11) Uani 1 1 d . . .
H32A H 0.9250 0.1104 0.2098 0.063 Uiso 1 1 calc R . .
C23 C 0.5823(3) 0.1486(4) 0.0819(3) 0.0475(11) Uani 1 1 d . . .
H26A H 0.5741 0.2255 0.0625 0.057 Uiso 1 1 calc R . .
C15 C 0.8384(3) 0.0679(4) 0.2755(3) 0.0490(11) Uani 1 1 d . . .
H31A H 0.8313 0.1438 0.2922 0.059 Uiso 1 1 calc R . .
C21 C 0.6303(3) -0.0475(4) 0.0724(3) 0.0454(10) Uani 1 1 d . . .
C30 C 0.4122(3) -0.0444(4) 0.3739(3) 0.0509(11) Uani 1 1 d . . .
H36A H 0.4255 -0.1211 0.3558 0.061 Uiso 1 1 calc R . .
H36B H 0.4641 -0.0285 0.4290 0.061 Uiso 1 1 calc R . .
C6 C 0.9398(3) 0.2604(4) 0.5726(3) 0.0578(12) Uani 1 1 d . . .
H22A H 0.9943 0.2919 0.6172 0.069 Uiso 1 1 calc R . .
C26 C 0.3335(4) 0.0326(4) 0.2251(3) 0.0597(13) Uani 1 1 d . . .
H38A H 0.3443 -0.0393 0.1993 0.072 Uiso 1 1 calc R . .
H38B H 0.3354 0.0972 0.1887 0.072 Uiso 1 1 calc R . .
C7 C 0.8700(4) 0.3345(4) 0.5149(3) 0.0543(12) Uani 1 1 d . . .
H23A H 0.8752 0.4153 0.5221 0.065 Uiso 1 1 calc R . .
C3 C 0.8386(4) -0.0417(4) 0.4889(3) 0.0545(12) Uani 1 1 d . . .
H19A H 0.8956 -0.0739 0.4777 0.065 Uiso 1 1 calc R . .
H19B H 0.8404 -0.0739 0.5421 0.065 Uiso 1 1 calc R . .
C37 C 0.3089(4) -0.0448(4) 0.3809(3) 0.0618(13) Uani 1 1 d . . .
H37A H 0.2982 0.0292 0.4043 0.074 Uiso 1 1 calc R . .
H37B H 0.3064 -0.1068 0.4190 0.074 Uiso 1 1 calc R . .
C28 C 0.2254(4) -0.0635(4) 0.2947(4) 0.0656(14) Uani 1 1 d . . .
H10A H 0.2327 -0.1405 0.2737 0.079 Uiso 1 1 calc R . .
H10B H 0.1597 -0.0602 0.3002 0.079 Uiso 1 1 calc R . .
C8 C 0.7931(3) 0.2857(4) 0.4471(3) 0.0491(11) Uani 1 1 d . . .
H2A H 0.7473 0.3346 0.4072 0.059 Uiso 1 1 calc R . .
C5 C 0.9286(3) 0.1408(4) 0.5642(3) 0.0558(12) Uani 1 1 d . . .
H21A H 0.9747 0.0925 0.6043 0.067 Uiso 1 1 calc R . .
C27 C 0.2297(4) 0.0287(5) 0.2322(3) 0.0670(14) Uani 1 1 d . . .
H4A H 0.2148 0.1048 0.2502 0.080 Uiso 1 1 calc R . .
H4B H 0.1781 0.0120 0.1770 0.080 Uiso 1 1 calc R . .
O4 O 0.9652(2) -0.0751(3) 0.1514(2) 0.0597(9) Uani 1 1 d . . .
N3 N 0.6724(3) -0.1364(3) 0.0317(2) 0.0535(10) Uani 1 1 d . . .
O1 O 0.5226(3) -0.1408(2) 0.2606(2) 0.0575(9) Uani 1 1 d . . .
O2 O 0.6701(3) -0.2388(3) 0.0511(2) 0.0694(10) Uani 1 1 d . . .
O3 O 0.7087(3) -0.1035(3) -0.0200(2) 0.0700(10) Uani 1 1 d . . .
O5 O 0.5741(2) 0.1876(2) 0.40885(18) 0.0512(8) Uani 1 1 d . . .
C17 C 0.5928(3) 0.1209(3) 0.3605(3) 0.0405(9) Uani 1 1 d . . .
C16 C 0.9681(4) -0.1859(5) 0.1155(4) 0.0734(15) Uani 1 1 d . . .
H10C H 1.0085 -0.1813 0.0812 0.110 Uiso 1 1 calc R . .
H10D H 0.9003 -0.2097 0.0811 0.110 Uiso 1 1 calc R . .
H10E H 0.9975 -0.2421 0.1599 0.110 Uiso 1 1 calc R . .
H25 H 0.416(3) 0.119(3) 0.341(2) 0.037(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
C18 O1 1.221(4) . ?
C18 N2 1.462(5) . ?
C18 C19 1.478(6) . ?
C20 C21 1.374(6) . ?
C20 C19 1.396(6) . ?
C9 C8 1.390(6) . ?
C9 C4 1.399(6) . ?
C9 C1 1.522(6) . ?
C25 N2 1.491(5) . ?
C25 C26 1.513(6) . ?
C25 C30 1.524(6) . ?
C1 N1 1.458(5) . ?
C1 C17 1.541(6) . ?
N1 C10 1.427(5) . ?
N1 C2 1.486(5) . ?
C19 C24 1.397(5) . ?
C11 C10 1.395(5) . ?
C11 C12 1.396(6) . ?
C2 C3 1.519(6) . ?
C22 C23 1.374(6) . ?
C22 C21 1.382(6) . ?
C12 C13 1.376(6) . ?
N2 C17 1.381(5) . ?
C24 C23 1.395(6) . ?
C10 C15 1.383(6) . ?
C4 C5 1.390(6) . ?
C4 C3 1.523(6) . ?
C13 O4 1.372(5) . ?
C13 C14 1.389(6) . ?
C14 C15 1.380(6) . ?
C21 N3 1.476(5) . ?
C30 C37 1.514(6) . ?
C6 C5 1.377(7) . ?
C6 C7 1.391(6) . ?
C26 C27 1.523(7) . ?
C7 C8 1.377(6) . ?
C37 C28 1.518(7) . ?
C28 C27 1.515(7) . ?
O4 C16 1.413(6) . ?
N3 O2 1.220(5) . ?
N3 O3 1.233(5) . ?
O5 C17 1.220(5) . ?

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
O1 C18 N2 118.6(3) . . ?
O1 C18 C19 122.2(4) . . ?
N2 C18 C19 118.0(3) . . ?
C21 C20 C19 118.6(4) . . ?
C8 C9 C4 119.5(4) . . ?
C8 C9 C1 120.4(4) . . ?
C4 C9 C1 120.0(4) . . ?
N2 C25 C26 111.5(4) . . ?
N2 C25 C30 112.1(3) . . ?
C26 C25 C30 111.8(4) . . ?
N1 C1 C9 112.5(3) . . ?
N1 C1 C17 110.1(3) . . ?
C9 C1 C17 113.1(3) . . ?
C10 N1 C1 118.0(3) . . ?
C10 N1 C2 116.1(3) . . ?
C1 N1 C2 109.1(3) . . ?
C20 C19 C24 119.2(4) . . ?
C20 C19 C18 116.6(3) . . ?
C24 C19 C18 124.2(4) . . ?
C10 C11 C12 121.2(4) . . ?
N1 C2 C3 110.2(3) . . ?
C23 C22 C21 118.2(4) . . ?
C13 C12 C11 120.0(4) . . ?
C17 N2 C18 124.1(3) . . ?
C17 N2 C25 117.1(3) . . ?
C18 N2 C25 117.5(3) . . ?
C23 C24 C19 120.3(4) . . ?
C15 C10 C11 118.2(4) . . ?
C15 C10 N1 122.5(4) . . ?
C11 C10 N1 119.2(4) . . ?
C5 C4 C9 118.5(4) . . ?
C5 C4 C3 120.4(4) . . ?
C9 C4 C3 121.1(4) . . ?
O4 C13 C12 124.6(4) . . ?
O4 C13 C14 116.7(4) . . ?
C12 C13 C14 118.6(4) . . ?
C15 C14 C13 121.5(4) . . ?
C22 C23 C24 120.5(4) . . ?
C14 C15 C10 120.4(4) . . ?
C20 C21 C22 123.1(4) . . ?
C20 C21 N3 118.3(4) . . ?
C22 C21 N3 118.6(4) . . ?
C37 C30 C25 111.4(4) . . ?
C5 C6 C7 120.4(4) . . ?
C25 C26 C27 111.4(4) . . ?
C8 C7 C6 118.6(4) . . ?
C2 C3 C4 112.2(3) . . ?
C30 C37 C28 110.7(4) . . ?
C27 C28 C37 111.1(4) . . ?
C7 C8 C9 121.7(4) . . ?
C6 C5 C4 121.2(4) . . ?
C28 C27 C26 111.8(4) . . ?
C13 O4 C16 117.4(4) . . ?
O2 N3 O3 123.1(4) . . ?
O2 N3 C21 118.4(4) . . ?
O3 N3 C21 118.5(4) . . ?
O5 C17 N2 122.5(4) . . ?
O5 C17 C1 121.1(3) . . ?
N2 C17 C1 116.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.112
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc and Hexane'
