# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_2013ncs0785
_database_code_depnum_ccdc_archive 'CCDC 1019568'
_audit_update_record             
;
2014-08-15 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H48 N2 O4'
_chemical_formula_weight         764.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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                   20.5116(14)
_cell_length_b                   5.1146(4)
_cell_length_c                   21.4898(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.490(2)
_cell_angle_gamma                90.00
_cell_volume                     2017.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16680
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.5


_exptl_crystal_description       Needle
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.699

_exptl_absorpt_process_details   ?

_exptl_special_details           
;
Data collected by the NCS as 2013ncs0785
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  Mirrors

_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20043
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_sigmaI/netI    0.0637
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4616
_reflns_number_gt                3144
_reflns_threshold_expression     I>2σ(I)

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0569P)²+0.3576P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4616
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
O1 O 0.40037(6) 1.5915(2) 0.35108(6) 0.0175(3) Uani 1 1 d . . .
O2 O 0.36168(6) 0.0141(2) 0.82301(6) 0.0191(3) Uani 1 1 d . . .
N1 N 0.39591(6) 1.3297(3) 0.43755(7) 0.0132(3) Uani 1 1 d . . .
C1 C 0.42894(8) 1.5180(3) 0.41165(8) 0.0138(3) Uani 1 1 d . . .
C2 C 0.50224(8) 1.4218(3) 0.52809(8) 0.0128(3) Uani 1 1 d . . .
C3 C 0.44004(8) 1.2719(3) 0.50748(8) 0.0118(3) Uani 1 1 d . . .
C4 C 0.33014(8) 1.1945(3) 0.38805(8) 0.0139(3) Uani 1 1 d . . .
H4A H 0.3254 1.0269 0.4087 0.017 Uiso 1 1 calc R . .
H4B H 0.3354 1.1536 0.3455 0.017 Uiso 1 1 calc R . .
C5 C 0.26122(8) 1.3539(3) 0.36817(8) 0.0128(3) Uani 1 1 d . . .
C6 C 0.25673(8) 1.5489(3) 0.41098(9) 0.0166(4) Uani 1 1 d . . .
H6 H 0.2975 1.5834 0.4543 0.020 Uiso 1 1 calc R . .
C7 C 0.19323(9) 1.6948(4) 0.39142(9) 0.0198(4) Uani 1 1 d . . .
H7 H 0.1909 1.8283 0.4211 0.024 Uiso 1 1 calc R . .
C8 C 0.13309(9) 1.6439(4) 0.32809(10) 0.0208(4) Uani 1 1 d . . .
H8 H 0.0897 1.7431 0.3144 0.025 Uiso 1 1 calc R . .
C9 C 0.13683(8) 1.4481(4) 0.28520(9) 0.0208(4) Uani 1 1 d . . .
H9 H 0.0957 1.4120 0.2422 0.025 Uiso 1 1 calc R . .
C10 C 0.20062(8) 1.3039(4) 0.30483(9) 0.0177(4) Uani 1 1 d . . .
H10 H 0.2029 1.1709 0.2750 0.021 Uiso 1 1 calc R . .
C11 C 0.42186(8) 1.0881(3) 0.54949(8) 0.0126(3) Uani 1 1 d . . .
C12 C 0.35090(8) 1.0339(3) 0.54083(8) 0.0152(4) Uani 1 1 d . . .
H12 H 0.3104 1.1189 0.5050 0.018 Uiso 1 1 calc R . .
C13 C 0.33966(8) 0.8576(3) 0.58419(9) 0.0157(4) Uani 1 1 d . . .
H13 H 0.2913 0.8245 0.5774 0.019 Uiso 1 1 calc R . .
C14 C 0.39781(8) 0.7265(3) 0.63796(8) 0.0136(3) Uani 1 1 d . . .
C15 C 0.46823(8) 0.7879(3) 0.64700(8) 0.0144(3) Uani 1 1 d . . .
H15 H 0.5089 0.7064 0.6835 0.017 Uiso 1 1 calc R . .
C16 C 0.47987(8) 0.9635(3) 0.60423(8) 0.0141(3) Uani 1 1 d . . .
H16 H 0.5283 1.0005 0.6121 0.017 Uiso 1 1 calc R . .
C17 C 0.38730(8) 0.5353(3) 0.68463(8) 0.0136(3) Uani 1 1 d . . .
C18 C 0.32318(8) 0.5216(3) 0.69280(9) 0.0164(4) Uani 1 1 d . . .
H18 H 0.2839 0.6356 0.6665 0.020 Uiso 1 1 calc R . .
C19 C 0.31584(8) 0.3455(3) 0.73843(9) 0.0169(4) Uani 1 1 d . . .
H19 H 0.2718 0.3397 0.7428 0.020 Uiso 1 1 calc R . .
C20 C 0.37299(8) 0.1769(3) 0.77786(9) 0.0156(4) Uani 1 1 d . . .
C21 C 0.43685(8) 0.1837(3) 0.77006(9) 0.0167(4) Uani 1 1 d . . .
H21 H 0.4759 0.0686 0.7962 0.020 Uiso 1 1 calc R . .
C22 C 0.44307(8) 0.3596(3) 0.72382(9) 0.0169(4) Uani 1 1 d . . .
H22 H 0.4866 0.3610 0.7185 0.020 Uiso 1 1 calc R . .
C23 C 0.41927(9) -0.1655(4) 0.86264(9) 0.0193(4) Uani 1 1 d . . .
H23A H 0.4648 -0.0686 0.8907 0.023 Uiso 1 1 calc R . .
H23B H 0.4281 -0.2856 0.8311 0.023 Uiso 1 1 calc R . .
C24 C 0.39624(10) -0.3190(4) 0.90968(10) 0.0231(4) Uani 1 1 d . . .
H24A H 0.4326 -0.4581 0.9329 0.028 Uiso 1 1 calc R . .
H24B H 0.3491 -0.4052 0.8807 0.028 Uiso 1 1 calc R . .
C25 C 0.38822(10) -0.1563(4) 0.96501(10) 0.0272(4) Uani 1 1 d . . .
H25A H 0.3490 -0.0262 0.9421 0.033 Uiso 1 1 calc R . .
H25B H 0.4341 -0.0598 0.9921 0.033 Uiso 1 1 calc R . .
C26 C 0.37054(12) -0.3216(5) 1.01458(12) 0.0373(5) Uani 1 1 d . . .
H26A H 0.3248 -0.4158 0.9882 0.056 Uiso 1 1 calc R . .
H26B H 0.3656 -0.2077 1.0489 0.056 Uiso 1 1 calc R . .
H26C H 0.4099 -0.4474 1.0385 0.056 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 1.2241(19) . ?
O2 C20 1.375(2) . ?
O2 C23 1.438(2) . ?
N1 C3 1.397(2) . ?
N1 C1 1.426(2) . ?
N1 C4 1.4663(19) . ?
C1 C2 1.461(2) 3_686 ?
C2 C3 1.381(2) . ?
C2 C2 1.416(3) 3_686 ?
C2 C1 1.461(2) 3_686 ?
C3 C11 1.462(2) . ?
C4 C5 1.519(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.387(2) . ?
C5 C10 1.398(2) . ?
C6 C7 1.394(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.399(2) . ?
C11 C12 1.410(2) . ?
C12 C13 1.388(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.406(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.404(2) . ?
C14 C17 1.484(2) . ?
C15 C16 1.380(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.402(2) . ?
C17 C18 1.404(2) . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.396(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.393(2) . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.512(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.519(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.525(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
C20 O2 C23 116.90(13) . . ?
C3 N1 C1 111.73(12) . . ?
C3 N1 C4 128.72(14) . . ?
C1 N1 C4 118.63(13) . . ?
O1 C1 N1 122.48(14) . . ?
O1 C1 C2 133.87(15) . 3_686 ?
N1 C1 C2 103.63(13) . 3_686 ?
C3 C2 C2 109.91(16) . 3_686 ?
C3 C2 C1 142.21(16) . 3_686 ?
C2 C2 C1 107.85(17) 3_686 3_686 ?
C2 C3 N1 106.85(14) . . ?
C2 C3 C11 127.77(14) . . ?
N1 C3 C11 125.38(13) . . ?
N1 C4 C5 112.98(14) . . ?
N1 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
N1 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C10 118.95(15) . . ?
C6 C5 C4 121.88(14) . . ?
C10 C5 C4 119.17(15) . . ?
C5 C6 C7 120.97(15) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 119.69(17) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 119.78(16) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.26(15) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 120.34(16) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C16 C11 C12 117.53(15) . . ?
C16 C11 C3 117.16(13) . . ?
C12 C11 C3 125.27(14) . . ?
C13 C12 C11 120.65(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.83(14) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 116.75(15) . . ?
C15 C14 C17 120.29(14) . . ?
C13 C14 C17 122.95(14) . . ?
C16 C15 C14 121.75(15) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C11 121.44(14) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C22 C17 C18 116.85(15) . . ?
C22 C17 C14 120.19(14) . . ?
C18 C17 C14 122.95(14) . . ?
C19 C18 C17 121.56(15) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 120.21(15) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
O2 C20 C21 124.32(15) . . ?
O2 C20 C19 116.24(14) . . ?
C21 C20 C19 119.44(16) . . ?
C22 C21 C20 119.60(15) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C17 122.32(15) . . ?
C21 C22 H22 118.8 . . ?
C17 C22 H22 118.8 . . ?
O2 C23 C24 107.96(14) . . ?
O2 C23 H23A 110.1 . . ?
C24 C23 H23A 110.1 . . ?
O2 C23 H23B 110.1 . . ?
C24 C23 H23B 110.1 . . ?
H23A C23 H23B 108.4 . . ?
C23 C24 C25 114.48(16) . . ?
C23 C24 H24A 108.6 . . ?
C25 C24 H24A 108.6 . . ?
C23 C24 H24B 108.6 . . ?
C25 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?
C24 C25 C26 112.70(18) . . ?
C24 C25 H25A 109.1 . . ?
C26 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
C26 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 O1 178.07(15) . . . . ?
C4 N1 C1 O1 8.1(2) . . . . ?
C3 N1 C1 C2 -0.91(18) . . . 3_686 ?
C4 N1 C1 C2 -170.88(13) . . . 3_686 ?
C2 C2 C3 N1 0.8(2) 3_686 . . . ?
C1 C2 C3 N1 178.7(2) 3_686 . . . ?
C2 C2 C3 C11 -178.73(18) 3_686 . . . ?
C1 C2 C3 C11 -0.8(3) 3_686 . . . ?
C1 N1 C3 C2 0.12(18) . . . . ?
C4 N1 C3 C2 168.82(15) . . . . ?
C1 N1 C3 C11 179.63(15) . . . . ?
C4 N1 C3 C11 -11.7(3) . . . . ?
C3 N1 C4 C5 110.13(18) . . . . ?
C1 N1 C4 C5 -81.84(18) . . . . ?
N1 C4 C5 C6 -23.9(2) . . . . ?
N1 C4 C5 C10 155.82(15) . . . . ?
C10 C5 C6 C7 -0.4(3) . . . . ?
C4 C5 C6 C7 179.31(16) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
C6 C5 C10 C9 0.0(3) . . . . ?
C4 C5 C10 C9 -179.72(16) . . . . ?
C2 C3 C11 C16 -29.2(2) . . . . ?
N1 C3 C11 C16 151.35(15) . . . . ?
C2 C3 C11 C12 148.32(17) . . . . ?
N1 C3 C11 C12 -31.1(3) . . . . ?
C16 C11 C12 C13 -1.7(2) . . . . ?
C3 C11 C12 C13 -179.27(16) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 1.7(3) . . . . ?
C12 C13 C14 C17 -179.43(16) . . . . ?
C13 C14 C15 C16 -1.5(3) . . . . ?
C17 C14 C15 C16 179.57(15) . . . . ?
C14 C15 C16 C11 -0.3(3) . . . . ?
C12 C11 C16 C15 1.9(2) . . . . ?
C3 C11 C16 C15 179.66(15) . . . . ?
C15 C14 C17 C22 -18.8(2) . . . . ?
C13 C14 C17 C22 162.37(16) . . . . ?
C15 C14 C17 C18 160.35(16) . . . . ?
C13 C14 C17 C18 -18.5(3) . . . . ?
C22 C17 C18 C19 1.1(2) . . . . ?
C14 C17 C18 C19 -178.10(16) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C23 O2 C20 C21 -2.2(2) . . . . ?
C23 O2 C20 C19 178.39(15) . . . . ?
C18 C19 C20 O2 178.30(15) . . . . ?
C18 C19 C20 C21 -1.2(3) . . . . ?
O2 C20 C21 C22 -178.76(16) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C20 C21 C22 C17 0.7(3) . . . . ?
C18 C17 C22 C21 -1.6(2) . . . . ?
C14 C17 C22 C21 177.60(16) . . . . ?
C20 O2 C23 C24 178.60(14) . . . . ?
O2 C23 C24 C25 -65.33(19) . . . . ?
C23 C24 C25 C26 -175.69(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.057
