# Electronic Supplementary Material (ESI) for ChemComm.
# 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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_22

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H45 N3 O6'
_chemical_formula_weight         651.78

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           RHOMBOHEDRAL
_symmetry_space_group_name_H-M   R3C

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'-y, -x, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'-y+2/3, -x+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'
'-y+1/3, -x+2/3, z+7/6'

_cell_length_a                   25.053(2)
_cell_length_b                   25.053(2)
_cell_length_c                   9.6450(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     5242.7(9)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2088
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9786
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_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            9716
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2054
_reflns_number_gt                1481
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0782P)²+5.0595P] 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     SHELXL
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         2054
_refine_ls_number_parameters     151
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1525
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.086
_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
C3 C 0.19815(18) -0.02295(17) 0.2453(3) 0.0392(9) Uani 1 1 d . . .
N1 N 0.13849(15) -0.06943(15) 0.2064(3) 0.0391(8) Uani 1 1 d . . .
C8 C 0.22763(17) 0.03387(17) 0.1742(4) 0.0381(9) Uani 1 1 d . . .
C9 C 0.19758(19) 0.05399(18) 0.0701(4) 0.0447(10) Uani 1 1 d . . .
C2 C 0.09395(19) -0.10841(18) 0.2944(4) 0.0431(10) Uani 1 1 d . . .
O1 O 0.09969(15) -0.10320(16) 0.4201(3) 0.0632(9) Uani 1 1 d . . .
O2 O 0.32360(15) 0.12854(16) 0.1359(4) 0.0732(11) Uani 1 1 d . . .
C12 C 0.1382(2) 0.03757(18) 0.0678(5) 0.0501(11) Uani 1 1 d . . .
H12 H 0.1135 0.0098 0.1357 0.060 Uiso 1 1 calc R . .
C4 C 0.2297(2) -0.0352(2) 0.3466(4) 0.0516(11) Uani 1 1 d . . .
H4 H 0.2100 -0.0727 0.3935 0.062 Uiso 1 1 calc R . .
C1 C 0.0367(2) -0.1585(2) 0.2271(5) 0.0567(12) Uani 1 1 d . . .
H1A H 0.0413 -0.1550 0.1281 0.085 Uiso 1 1 calc R . .
H1B H 0.0019 -0.1547 0.2542 0.085 Uiso 1 1 calc R . .
H1C H 0.0304 -0.1980 0.2558 0.085 Uiso 1 1 calc R . .
C6 C 0.3208(2) 0.0616(2) 0.3062(4) 0.0556(12) Uani 1 1 d . . .
H6 H 0.3620 0.0894 0.3252 0.067 Uiso 1 1 calc R . .
C7 C 0.2900(2) 0.0747(2) 0.2039(4) 0.0490(10) Uani 1 1 d . . .
C10 C 0.2423(2) 0.1012(3) -0.0305(6) 0.089(2) Uani 1 1 d . . .
H10A H 0.2453 0.0799 -0.1115 0.107 Uiso 1 1 calc R . .
H10B H 0.2258 0.1270 -0.0607 0.107 Uiso 1 1 calc R . .
C13 C 0.1070(2) 0.0585(2) -0.0306(6) 0.0758(15) Uani 1 1 d . . .
H13A H 0.0640 0.0393 -0.0076 0.114 Uiso 1 1 calc R . .
H13B H 0.1114 0.0472 -0.1233 0.114 Uiso 1 1 calc R . .
H13C H 0.1253 0.1024 -0.0248 0.114 Uiso 1 1 calc R . .
C5 C 0.2901(2) 0.0074(2) 0.3790(5) 0.0610(13) Uani 1 1 d . . .
H5 H 0.3100 -0.0006 0.4504 0.073 Uiso 1 1 calc R . .
C11 C 0.2989(4) 0.1374(4) 0.0201(9) 0.139(3) Uani 1 1 d U . .
H11A H 0.3029 0.1777 0.0309 0.167 Uiso 1 1 calc R . .
H11B H 0.3268 0.1415 -0.0542 0.167 Uiso 1 1 calc R . .
H1N H 0.1318(19) -0.0678(19) 0.130(5) 0.039(12) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C3 0.048(2) 0.048(2) 0.0240(17) -0.0047(16) -0.0001(16) 0.026(2)
N1 0.046(2) 0.0445(19) 0.0207(17) 0.0028(14) -0.0012(14) 0.0177(16)
C8 0.043(2) 0.041(2) 0.0314(19) -0.0064(16) -0.0013(16) 0.0221(18)
C9 0.050(2) 0.038(2) 0.037(2) -0.0018(17) -0.0078(18) 0.0145(19)
C2 0.049(2) 0.047(2) 0.033(2) 0.0076(18) 0.0054(18) 0.024(2)
O1 0.075(2) 0.077(2) 0.0270(15) 0.0103(14) 0.0085(14) 0.0297(17)
O2 0.0510(19) 0.055(2) 0.090(3) 0.0072(17) -0.0123(18) 0.0090(16)
C12 0.060(3) 0.042(2) 0.051(2) -0.002(2) -0.009(2) 0.027(2)
C4 0.063(3) 0.060(3) 0.040(2) 0.0020(19) -0.005(2) 0.036(2)
C1 0.049(2) 0.065(3) 0.049(2) 0.009(2) 0.006(2) 0.023(2)
C6 0.050(3) 0.073(3) 0.051(2) -0.020(3) -0.012(2) 0.036(2)
C7 0.048(3) 0.049(2) 0.049(2) -0.0090(19) -0.002(2) 0.024(2)
C10 0.072(4) 0.075(4) 0.061(3) 0.023(3) -0.014(3) -0.007(3)
C13 0.071(3) 0.067(3) 0.088(4) 0.007(3) -0.025(3) 0.033(3)
C5 0.066(3) 0.085(4) 0.045(3) -0.011(3) -0.013(2) 0.048(3)
C11 0.103(4) 0.142(5) 0.126(5) 0.058(4) -0.022(4) 0.027(3)

_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
C3 C4 1.384(5) . ?
C3 N1 1.411(5) . ?
C3 C8 1.411(5) . ?
N1 C2 1.353(5) . ?
N1 H1N 0.76(5) . ?
C8 C7 1.404(6) . ?
C8 C9 1.486(6) . ?
C9 C12 1.330(5) . ?
C9 C10 1.507(6) . ?
C2 O1 1.220(4) . ?
C2 C1 1.501(6) . ?
O2 C11 1.347(7) . ?
O2 C7 1.350(6) . ?
C12 C13 1.483(6) . ?
C12 H12 0.9300 . ?
C4 C5 1.383(7) . ?
C4 H4 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C6 C5 1.372(7) . ?
C6 C7 1.390(6) . ?
C6 H6 0.9300 . ?
C10 C11 1.337(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C5 H5 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
C4 C3 N1 119.4(4) . . ?
C4 C3 C8 119.9(4) . . ?
N1 C3 C8 120.5(3) . . ?
C2 N1 C3 125.4(3) . . ?
C2 N1 H1N 122(3) . . ?
C3 N1 H1N 113(3) . . ?
C7 C8 C3 117.8(4) . . ?
C7 C8 C9 117.3(4) . . ?
C3 C8 C9 124.9(3) . . ?
C12 C9 C8 125.7(4) . . ?
C12 C9 C10 120.7(4) . . ?
C8 C9 C10 113.4(4) . . ?
O1 C2 N1 122.4(4) . . ?
O1 C2 C1 122.1(4) . . ?
N1 C2 C1 115.5(4) . . ?
C11 O2 C7 117.3(4) . . ?
C9 C12 C13 127.4(4) . . ?
C9 C12 H12 116.3 . . ?
C13 C12 H12 116.3 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C6 C7 119.6(4) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
O2 C7 C6 116.0(4) . . ?
O2 C7 C8 122.7(4) . . ?
C6 C7 C8 121.4(4) . . ?
C11 C10 C9 114.7(5) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C10 C11 O2 127.6(6) . . ?
C10 C11 H11A 105.4 . . ?
O2 C11 H11A 105.4 . . ?
C10 C11 H11B 105.4 . . ?
O2 C11 H11B 105.4 . . ?
H11A C11 H11B 106.0 . . ?

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
C4 C3 N1 C2 41.5(6) . . . . ?
C8 C3 N1 C2 -143.7(4) . . . . ?
C4 C3 C8 C7 3.9(5) . . . . ?
N1 C3 C8 C7 -170.9(3) . . . . ?
C4 C3 C8 C9 -175.9(4) . . . . ?
N1 C3 C8 C9 9.3(5) . . . . ?
C7 C8 C9 C12 -150.2(4) . . . . ?
C3 C8 C9 C12 29.7(6) . . . . ?
C7 C8 C9 C10 24.4(5) . . . . ?
C3 C8 C9 C10 -155.7(4) . . . . ?
C3 N1 C2 O1 6.8(6) . . . . ?
C3 N1 C2 C1 -173.4(4) . . . . ?
C8 C9 C12 C13 177.4(4) . . . . ?
C10 C9 C12 C13 3.2(7) . . . . ?
N1 C3 C4 C5 174.5(4) . . . . ?
C8 C3 C4 C5 -0.3(6) . . . . ?
C11 O2 C7 C6 167.9(6) . . . . ?
C11 O2 C7 C8 -12.1(8) . . . . ?
C5 C6 C7 O2 -179.3(4) . . . . ?
C5 C6 C7 C8 0.7(6) . . . . ?
C3 C8 C7 O2 175.9(4) . . . . ?
C9 C8 C7 O2 -4.3(6) . . . . ?
C3 C8 C7 C6 -4.1(5) . . . . ?
C9 C8 C7 C6 175.7(4) . . . . ?
C12 C9 C10 C11 145.8(7) . . . . ?
C8 C9 C10 C11 -29.1(8) . . . . ?
C7 C6 C5 C4 3.0(6) . . . . ?
C3 C4 C5 C6 -3.2(6) . . . . ?
C9 C10 C11 O2 15.1(14) . . . . ?
C7 O2 C11 C10 6.3(13) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 993319'
