# 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
#  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.
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data_ks

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H25 N O6'
_chemical_formula_sum            'C24 H25 N O6'
_chemical_formula_weight         423.45

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                   13.637(7)
_cell_length_b                   13.749(7)
_cell_length_c                   12.866(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.745(8)
_cell_angle_gamma                90.00
_cell_volume                     2241(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    8921
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25.12

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9734
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20931
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         25.12
_reflns_number_total             3985
_reflns_number_gt                2840
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1412P)²+0.4202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   constr
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3985
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.2115
_refine_ls_wR_factor_gt          0.1877
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          2.706
_refine_ls_shift/su_mean         0.028

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 0.60891(12) 0.10929(11) 0.19766(13) 0.0694(4) Uani 1 1 d . . .
N1 N 0.73576(15) 0.03905(14) 0.33991(16) 0.0704(5) Uani 1 1 d . . .
O6 O 0.57097(15) -0.16402(13) 0.50320(14) 0.0859(6) Uani 1 1 d . . .
C3 C 0.45521(17) 0.00836(16) 0.15815(18) 0.0637(6) Uani 1 1 d . . .
O1 O 0.97431(15) 0.40526(14) 0.22483(17) 0.0950(6) Uani 1 1 d . . .
C9 C 0.77699(17) 0.18938(17) 0.25720(19) 0.0662(6) Uani 1 1 d . . .
O5 O 0.63975(17) -0.01538(14) 0.53368(16) 0.0967(6) Uani 1 1 d . . .
C23 C 0.71102(17) 0.11090(17) 0.26989(19) 0.0674(6) Uani 1 1 d . . .
C12 C 0.90492(19) 0.33614(17) 0.2304(2) 0.0721(6) Uani 1 1 d . . .
C4 C 0.39310(18) -0.05058(18) 0.19532(19) 0.0709(6) Uani 1 1 d . . .
H4 H 0.4211 -0.0774 0.2667 0.085 Uiso 1 1 calc R . .
C1 C 0.56541(17) 0.02770(17) 0.22553(18) 0.0648(6) Uani 1 1 d . . .
C11 C 0.8035(2) 0.32732(18) 0.1554(2) 0.0771(7) Uani 1 1 d . . .
H11 H 0.7775 0.3700 0.0953 0.093 Uiso 1 1 calc R . .
C14 C 0.88010(18) 0.19976(18) 0.3328(2) 0.0735(6) Uani 1 1 d . . .
H14 H 0.9064 0.1572 0.3930 0.088 Uiso 1 1 calc R . .
C18 C 0.61897(19) -0.08802(17) 0.4794(2) 0.0710(6) Uani 1 1 d . . .
C10 C 0.7402(2) 0.25455(19) 0.1699(2) 0.0793(7) Uani 1 1 d . . .
H10 H 0.6709 0.2493 0.1195 0.095 Uiso 1 1 calc R . .
C5 C 0.28971(19) -0.07021(19) 0.1275(2) 0.0775(7) Uani 1 1 d . . .
H5 H 0.2497 -0.1107 0.1541 0.093 Uiso 1 1 calc R . .
C13 C 0.94331(19) 0.27204(19) 0.3194(2) 0.0772(7) Uani 1 1 d . . .
H13 H 1.0123 0.2782 0.3703 0.093 Uiso 1 1 calc R . .
C2 C 0.64355(17) -0.01507(16) 0.31259(18) 0.0654(6) Uani 1 1 d . . .
C17 C 0.64139(19) -0.10662(17) 0.3741(2) 0.0679(6) Uani 1 1 d . . .
H17 H 0.586(2) -0.1486(18) 0.325(2) 0.081 Uiso 1 1 calc . . .
C6 C 0.24443(19) -0.0315(2) 0.0219(2) 0.0783(7) Uani 1 1 d . . .
O3 O 0.80772(17) -0.16835(17) 0.50020(19) 0.1179(8) Uani 1 1 d . . .
O4 O 0.75656(16) -0.19695(17) 0.3173(2) 0.1097(7) Uani 1 1 d . . .
C8 C 0.4090(2) 0.0489(2) 0.0526(2) 0.0861(8) Uani 1 1 d . . .
H8 H 0.4484 0.0903 0.0261 0.103 Uiso 1 1 calc R . .
C16 C 0.7455(2) -0.16055(18) 0.4069(3) 0.0804(7) Uani 1 1 d . . .
C7 C 0.3053(2) 0.0289(3) -0.0141(2) 0.0976(9) Uani 1 1 d . . .
H7 H 0.2764 0.0569 -0.0848 0.117 Uiso 1 1 calc R . .
C20 C 0.5472(3) -0.1560(2) 0.6044(3) 0.1087(10) Uani 1 1 d . . .
H20A H 0.6125 -0.1506 0.6690 0.130 Uiso 1 1 calc R . .
H20B H 0.5060 -0.0977 0.6006 0.130 Uiso 1 1 calc R . .
C22 C 0.1309(2) -0.0543(3) -0.0507(3) 0.1098(11) Uani 1 1 d . . .
H22A H 0.1241 -0.1225 -0.0678 0.165 Uiso 1 1 calc R . .
H22B H 0.1111 -0.0176 -0.1189 0.165 Uiso 1 1 calc R . .
H22C H 0.0857 -0.0372 -0.0115 0.165 Uiso 1 1 calc R . .
C15 C 0.9389(3) 0.4730(3) 0.1354(3) 0.1222(13) Uani 1 1 d . . .
H15A H 0.9180 0.4389 0.0654 0.183 Uiso 1 1 calc R . .
H15B H 0.9950 0.5174 0.1411 0.183 Uiso 1 1 calc R . .
H15C H 0.8797 0.5085 0.1392 0.183 Uiso 1 1 calc R . .
C24 C 0.4908(3) -0.2374(3) 0.6166(3) 0.1318(14) Uani 1 1 d . . .
H24A H 0.4243 -0.2406 0.5548 0.198 Uiso 1 1 calc R . .
H24B H 0.4787 -0.2323 0.6852 0.198 Uiso 1 1 calc R . .
H24C H 0.5308 -0.2953 0.6180 0.198 Uiso 1 1 calc R . .
C30 C 0.8541(3) -0.2498(4) 0.3326(6) 0.172(2) Uani 1 1 d . . .
H30A H 0.8857 -0.2210 0.2836 0.206 Uiso 1 1 calc R . .
H30B H 0.9027 -0.2395 0.4089 0.206 Uiso 1 1 calc R . .
C31 C 0.8459(4) -0.3409(4) 0.3143(7) 0.216(4) Uani 1 1 d . . .
H31A H 0.8246 -0.3721 0.3693 0.324 Uiso 1 1 calc R . .
H31B H 0.9129 -0.3665 0.3189 0.324 Uiso 1 1 calc R . .
H31C H 0.7942 -0.3530 0.2411 0.324 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 C23 1.358(3) . ?
O2 C1 1.377(3) . ?
N1 C23 1.295(3) . ?
N1 C2 1.390(3) . ?
O6 C18 1.328(3) . ?
O6 C20 1.458(4) . ?
C3 C4 1.379(3) . ?
C3 C8 1.385(3) . ?
C3 C1 1.454(3) . ?
O1 C12 1.362(3) . ?
O1 C15 1.418(4) . ?
C9 C10 1.378(3) . ?
C9 C14 1.389(3) . ?
C9 C23 1.452(3) . ?
O5 C18 1.191(3) . ?
C12 C11 1.367(3) . ?
C12 C13 1.385(4) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C1 C2 1.361(3) . ?
C11 C10 1.379(4) . ?
C11 H11 0.9300 . ?
C14 C13 1.368(3) . ?
C14 H14 0.9300 . ?
C18 C17 1.517(4) . ?
C10 H10 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C13 H13 0.9300 . ?
C2 C17 1.493(3) . ?
C17 C16 1.516(4) . ?
C17 H17 1.04(3) . ?
C6 C7 1.371(4) . ?
C6 C22 1.515(4) . ?
O3 C16 1.191(3) . ?
O4 C16 1.316(4) . ?
O4 C30 1.464(4) . ?
C8 C7 1.383(4) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C20 C24 1.399(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C30 C31 1.273(5) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

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
C23 O2 C1 105.46(17) . . ?
C23 N1 C2 104.75(18) . . ?
C18 O6 C20 116.0(2) . . ?
C4 C3 C8 117.5(2) . . ?
C4 C3 C1 122.2(2) . . ?
C8 C3 C1 120.3(2) . . ?
C12 O1 C15 117.8(2) . . ?
C10 C9 C14 118.2(2) . . ?
C10 C9 C23 121.4(2) . . ?
C14 C9 C23 120.4(2) . . ?
N1 C23 O2 113.6(2) . . ?
N1 C23 C9 129.2(2) . . ?
O2 C23 C9 117.1(2) . . ?
O1 C12 C11 124.5(2) . . ?
O1 C12 C13 115.5(2) . . ?
C11 C12 C13 120.0(2) . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C2 C1 O2 106.55(19) . . ?
C2 C1 C3 137.1(2) . . ?
O2 C1 C3 116.32(19) . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C14 C9 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
O5 C18 O6 123.7(2) . . ?
O5 C18 C17 125.6(2) . . ?
O6 C18 C17 110.7(2) . . ?
C9 C10 C11 121.7(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C6 C5 C4 121.9(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C1 C2 N1 109.6(2) . . ?
C1 C2 C17 129.6(2) . . ?
N1 C2 C17 120.74(19) . . ?
C2 C17 C16 111.1(2) . . ?
C2 C17 C18 112.42(19) . . ?
C16 C17 C18 108.1(2) . . ?
C2 C17 H17 109.4(14) . . ?
C16 C17 H17 105.1(14) . . ?
C18 C17 H17 110.4(14) . . ?
C7 C6 C5 117.5(2) . . ?
C7 C6 C22 121.6(3) . . ?
C5 C6 C22 120.8(3) . . ?
C16 O4 C30 117.7(3) . . ?
C7 C8 C3 121.2(2) . . ?
C7 C8 H8 119.4 . . ?
C3 C8 H8 119.4 . . ?
O3 C16 O4 125.4(3) . . ?
O3 C16 C17 124.7(3) . . ?
O4 C16 C17 110.0(2) . . ?
C6 C7 C8 121.2(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C24 C20 O6 110.6(3) . . ?
C24 C20 H20A 109.5 . . ?
O6 C20 H20A 109.5 . . ?
C24 C20 H20B 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C6 C22 H22A 109.5 . . ?
C6 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C6 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.4 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C31 C30 O4 116.8(4) . . ?
C31 C30 H30A 108.1 . . ?
O4 C30 H30A 108.1 . . ?
C31 C30 H30B 108.1 . . ?
O4 C30 H30B 108.1 . . ?
H30A C30 H30B 107.3 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.12
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 1003921'
