# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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.
#
data_bmodeadcs

_audit_creation_method           SHELXL-97
_chemical_name_systematic        b-MODEADCS
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H38 N4 O2'
_chemical_formula_weight         534.68

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

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

_cell_length_a                   4.7039(2)
_cell_length_b                   9.3029(3)
_cell_length_c                   16.8491(6)
_cell_angle_alpha                100.068(2)
_cell_angle_beta                 92.587(2)
_cell_angle_gamma                99.396(2)
_cell_volume                     714.16(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6750
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.28

_exptl_crystal_description       Plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             286
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9749
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Turbo X-ray'
_diffrn_radiation_monochromator  Multilayer
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19580
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         28.45
_reflns_number_total             3574
_reflns_number_gt                2835
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0928P)²+0.2130P] 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         3574
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1712
_refine_ls_wR_factor_gt          0.1601
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.0155(2) 0.70190(10) -0.01026(7) 0.0387(3) Uani 1 1 d . . .
N1 N 0.6725(4) 1.24677(15) 0.21546(11) 0.0628(5) Uani 1 1 d . . .
N2 N 1.2869(3) 0.67329(15) 0.35101(8) 0.0426(4) Uani 1 1 d . . .
C1 C 0.1855(3) 1.10151(14) 0.05638(8) 0.0279(3) Uani 1 1 d . . .
H1A H 0.3127 1.1725 0.0949 0.033 Uiso 1 1 calc R . .
C2 C 0.1970(3) 0.95053(14) 0.05210(8) 0.0247(3) Uani 1 1 d . . .
C3 C 0.0039(3) 0.84948(14) -0.00661(8) 0.0269(3) Uani 1 1 d . . .
C4 C -0.1850(4) 0.59856(15) -0.06733(11) 0.0489(5) Uani 1 1 d . . .
H4A H -0.1556 0.4975 -0.0648 0.073 Uiso 1 1 calc R . .
H4B H -0.1544 0.6182 -0.1219 0.073 Uiso 1 1 calc R . .
H4C H -0.3826 0.6090 -0.0545 0.073 Uiso 1 1 calc R . .
C5 C 0.3919(3) 0.89347(14) 0.10327(8) 0.0268(3) Uani 1 1 d . . .
H5A H 0.3802 0.7889 0.0911 0.032 Uiso 1 1 calc R . .
C6 C 0.5877(3) 0.96290(14) 0.16536(8) 0.0257(3) Uani 1 1 d . . .
C7 C 0.6302(3) 1.12118(16) 0.19197(10) 0.0381(4) Uani 1 1 d . . .
C8 C 0.7711(3) 0.88696(14) 0.21178(8) 0.0262(3) Uani 1 1 d . . .
C9 C 0.7656(3) 0.73370(15) 0.19408(9) 0.0330(3) Uani 1 1 d . . .
H9A H 0.6422 0.6761 0.1497 0.040 Uiso 1 1 calc R . .
C10 C 0.9332(3) 0.66340(16) 0.23890(9) 0.0346(3) Uani 1 1 d . . .
H10A H 0.9208 0.5590 0.2248 0.041 Uiso 1 1 calc R . .
C11 C 1.1220(3) 0.74277(16) 0.30501(9) 0.0318(3) Uani 1 1 d . . .
C12 C 1.1309(3) 0.89681(17) 0.32205(9) 0.0362(3) Uani 1 1 d . . .
H12A H 1.2572 0.9552 0.3656 0.043 Uiso 1 1 calc R . .
C13 C 0.9600(3) 0.96567(15) 0.27691(9) 0.0322(3) Uani 1 1 d . . .
H13A H 0.9717 1.0700 0.2908 0.039 Uiso 1 1 calc R . .
C14 C 1.3164(5) 0.5186(2) 0.32742(12) 0.0533(5) Uani 1 1 d . . .
H14A H 1.5245 0.5129 0.3260 0.064 Uiso 1 1 calc R . .
H14B H 1.2251 0.4810 0.2720 0.064 Uiso 1 1 calc R . .
C15 C 1.1864(6) 0.4212(2) 0.38139(15) 0.0683(6) Uani 1 1 d . . .
H15A H 1.2172 0.3197 0.3621 0.102 Uiso 1 1 calc R . .
H15B H 0.9786 0.4227 0.3816 0.102 Uiso 1 1 calc R . .
H15C H 1.2772 0.4565 0.4364 0.102 Uiso 1 1 calc R . .
C16 C 1.4758(4) 0.7589(2) 0.41949(12) 0.0482(5) Uani 1 1 d . . .
H16A H 1.5758 0.8509 0.4040 0.058 Uiso 1 1 calc R . .
H16B H 1.6250 0.7009 0.4322 0.058 Uiso 1 1 calc R . .
C17 C 1.3211(5) 0.8000(2) 0.49459(11) 0.0624(6) Uani 1 1 d . . .
H17A H 1.4613 0.8569 0.5382 0.094 Uiso 1 1 calc R . .
H17B H 1.2247 0.7096 0.5112 0.094 Uiso 1 1 calc R . .
H17C H 1.1769 0.8602 0.4831 0.094 Uiso 1 1 calc R . .

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
O1 0.0529(7) 0.0171(5) 0.0433(6) 0.0021(4) -0.0201(5) 0.0075(4)
N1 0.0803(12) 0.0285(7) 0.0720(11) -0.0052(7) -0.0423(9) 0.0160(7)
N2 0.0549(8) 0.0421(7) 0.0380(7) 0.0143(6) -0.0039(6) 0.0240(6)
C1 0.0310(7) 0.0217(6) 0.0293(7) 0.0033(5) -0.0057(5) 0.0034(5)
C2 0.0264(6) 0.0213(6) 0.0267(6) 0.0052(5) -0.0003(5) 0.0051(5)
C3 0.0318(7) 0.0188(6) 0.0300(7) 0.0042(5) -0.0014(5) 0.0054(5)
C4 0.0704(11) 0.0196(7) 0.0503(10) 0.0004(6) -0.0280(8) 0.0041(7)
C5 0.0285(6) 0.0207(6) 0.0316(7) 0.0061(5) -0.0014(5) 0.0053(5)
C6 0.0264(6) 0.0211(6) 0.0303(7) 0.0056(5) 0.0000(5) 0.0061(5)
C7 0.0437(8) 0.0271(7) 0.0412(8) 0.0006(6) -0.0172(6) 0.0109(6)
C8 0.0257(6) 0.0239(6) 0.0296(7) 0.0064(5) 0.0002(5) 0.0056(5)
C9 0.0343(7) 0.0257(7) 0.0375(8) 0.0026(5) -0.0064(6) 0.0070(5)
C10 0.0387(8) 0.0251(6) 0.0422(8) 0.0077(6) 0.0002(6) 0.0116(6)
C11 0.0330(7) 0.0347(7) 0.0328(7) 0.0134(6) 0.0033(6) 0.0126(6)
C12 0.0396(8) 0.0327(7) 0.0359(8) 0.0073(6) -0.0095(6) 0.0076(6)
C13 0.0362(7) 0.0234(6) 0.0364(7) 0.0064(5) -0.0071(6) 0.0056(5)
C14 0.0734(13) 0.0490(10) 0.0498(10) 0.0200(8) 0.0035(9) 0.0351(9)
C15 0.0904(16) 0.0408(10) 0.0695(14) 0.0157(9) 0.0015(12) -0.0052(10)
C16 0.0352(8) 0.0519(10) 0.0620(11) 0.0302(8) -0.0125(7) 0.0043(7)
C17 0.0853(15) 0.0524(11) 0.0404(10) 0.0121(8) -0.0171(9) -0.0128(10)

_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 C3 1.3737(15) . ?
O1 C4 1.4272(17) . ?
N1 C7 1.147(2) . ?
N2 C11 1.3800(17) . ?
N2 C16 1.453(2) . ?
N2 C14 1.455(2) . ?
C1 C3 1.3796(17) 2_575 ?
C1 C2 1.4038(17) . ?
C2 C3 1.4150(17) . ?
C2 C5 1.4537(17) . ?
C3 C1 1.3796(17) 2_575 ?
C5 C6 1.3574(18) . ?
C6 C7 1.4402(18) . ?
C6 C8 1.4786(17) . ?
C8 C13 1.3959(18) . ?
C8 C9 1.4004(18) . ?
C9 C10 1.3809(19) . ?
C10 C11 1.409(2) . ?
C11 C12 1.405(2) . ?
C12 C13 1.3850(18) . ?
C14 C15 1.477(3) . ?
C16 C17 1.511(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
C3 O1 C4 116.78(10) . . ?
C11 N2 C16 120.33(13) . . ?
C11 N2 C14 122.72(14) . . ?
C16 N2 C14 116.29(13) . . ?
C3 C1 C2 122.39(11) 2_575 . ?
C1 C2 C3 116.53(11) . . ?
C1 C2 C5 124.43(11) . . ?
C3 C2 C5 119.04(11) . . ?
O1 C3 C1 122.69(11) . 2_575 ?
O1 C3 C2 116.23(11) . . ?
C1 C3 C2 121.08(11) 2_575 . ?
C6 C5 C2 131.49(12) . . ?
C5 C6 C7 121.24(11) . . ?
C5 C6 C8 124.59(11) . . ?
C7 C6 C8 114.16(11) . . ?
N1 C7 C6 177.24(15) . . ?
C13 C8 C9 116.08(11) . . ?
C13 C8 C6 121.17(12) . . ?
C9 C8 C6 122.74(11) . . ?
C10 C9 C8 122.29(13) . . ?
C9 C10 C11 121.58(13) . . ?
N2 C11 C12 121.81(13) . . ?
N2 C11 C10 122.03(13) . . ?
C12 C11 C10 116.16(12) . . ?
C13 C12 C11 121.62(13) . . ?
C12 C13 C8 122.26(13) . . ?
N2 C14 C15 114.29(17) . . ?
N2 C16 C17 113.97(15) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.45
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.058
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol and THF'
_database_code_depnum_ccdc_archive 'CCDC 1017042'
