# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1048902'
_audit_update_record             
;
2015-02-11 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'compound 2p'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H31 N O3'
_chemical_formula_sum            'C29 H31 N O3'
_chemical_formula_weight         441.55

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                   13.186(3)
_cell_length_b                   14.909(3)
_cell_length_c                   12.985(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.29(3)
_cell_angle_gamma                90.00
_cell_volume                     2394.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      6.10
_cell_measurement_theta_max      54.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.5704
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_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  'multiwire proportional'
_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            18411
_diffrn_reflns_av_R_equivalents  0.1157
_diffrn_reflns_av_sigmaI/netI    0.0897
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4215
_reflns_number_gt                2362
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.1657P)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     SHELXL
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4215
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.3089
_refine_ls_wR_factor_gt          0.2067
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_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
O1 O 0.6994(3) 0.01037(19) 0.5656(2) 0.0423(8) Uani 1 1 d . . .
O2 O 0.6198(2) -0.28984(18) 0.4115(2) 0.0390(8) Uani 1 1 d . . .
O3 O 0.5817(2) -0.1285(2) 0.3091(2) 0.0465(9) Uani 1 1 d . . .
H3A H 0.5772 -0.1776 0.3357 0.070 Uiso 1 1 calc R . .
C4 C 0.7224(3) -0.2796(2) 0.5002(3) 0.0346(10) Uani 1 1 d . . .
H4A H 0.7158 -0.3048 0.5673 0.042 Uiso 1 1 calc R . .
N1 N 0.9729(3) -0.1671(3) 0.7870(3) 0.0431(10) Uani 1 1 d . . .
C6 C 0.7452(3) -0.1781(3) 0.5174(3) 0.0331(10) Uani 1 1 d . . .
H6A H 0.6783 -0.1506 0.5192 0.040 Uiso 1 1 calc R . .
C7 C 0.9187(4) 0.0716(3) 0.8232(3) 0.0404(11) Uani 1 1 d . . .
H7A H 0.9421 0.1211 0.8689 0.048 Uiso 1 1 calc R . .
C8 C 0.9366(3) -0.0799(3) 0.7800(3) 0.0364(11) Uani 1 1 d . . .
C9 C 0.7902(3) 0.0098(3) 0.6569(3) 0.0334(10) Uani 1 1 d . . .
C10 C 0.8284(4) 0.0810(3) 0.7279(4) 0.0401(11) Uani 1 1 d . . .
H10A H 0.7933 0.1361 0.7119 0.048 Uiso 1 1 calc R . .
C11 C 0.8469(3) -0.0723(3) 0.6810(3) 0.0316(10) Uani 1 1 d . . .
C12 C 0.7710(4) -0.1319(3) 0.4230(3) 0.0353(10) Uani 1 1 d . . .
C13 C 0.6558(3) 0.1652(3) 0.5013(3) 0.0376(11) Uani 1 1 d . . .
C14 C 0.7999(4) -0.3366(3) 0.4665(4) 0.0433(12) Uani 1 1 d . . .
H14A H 0.8608 -0.3556 0.5297 0.052 Uiso 1 1 calc R . .
H14B H 0.8264 -0.3050 0.4157 0.052 Uiso 1 1 calc R . .
C15 C 0.9744(4) -0.0073(3) 0.8524(3) 0.0406(11) Uani 1 1 d . . .
H15A H 1.0341 -0.0126 0.9166 0.049 Uiso 1 1 calc R . .
C16 C 0.6145(4) 0.2472(3) 0.5154(4) 0.0518(13) Uani 1 1 d . . .
H16A H 0.5732 0.2516 0.5606 0.062 Uiso 1 1 calc R . .
C17 C 1.0617(4) -0.2044(4) 0.8782(4) 0.0583(14) Uani 1 1 d . . .
H17A H 1.0714 -0.2664 0.8639 0.087 Uiso 1 1 calc R . .
H17B H 1.0454 -0.1996 0.9445 0.087 Uiso 1 1 calc R . .
H17C H 1.1269 -0.1719 0.8864 0.087 Uiso 1 1 calc R . .
C18 C 0.7133(4) 0.1588(3) 0.4285(4) 0.0490(12) Uani 1 1 d . . .
H18A H 0.7393 0.1036 0.4152 0.059 Uiso 1 1 calc R . .
C19 C 0.7105(4) -0.0630(3) 0.2436(4) 0.0473(12) Uani 1 1 d . . .
H19A H 0.6546 -0.0475 0.1795 0.057 Uiso 1 1 calc R . .
C20 C 0.6881(4) -0.1096(3) 0.3266(4) 0.0390(11) Uani 1 1 d . . .
C21 C 0.8764(4) -0.1088(3) 0.4344(4) 0.0431(12) Uani 1 1 d . . .
H21A H 0.9328 -0.1249 0.4980 0.052 Uiso 1 1 calc R . .
C22 C 0.8305(4) -0.1589(3) 0.6274(3) 0.0392(11) Uani 1 1 d . . .
C23 C 0.6188(4) -0.3714(3) 0.3486(3) 0.0385(11) Uani 1 1 d . . .
C24 C 0.7307(4) 0.2359(3) 0.3764(4) 0.0559(14) Uani 1 1 d . . .
H24A H 0.7715 0.2328 0.3307 0.067 Uiso 1 1 calc R . .
C25 C 0.9076(4) -0.2127(3) 0.6964(4) 0.0447(12) Uani 1 1 d . . .
H25A H 0.9152 -0.2733 0.6838 0.054 Uiso 1 1 calc R . .
C26 C 0.7279(3) -0.4171(3) 0.4105(4) 0.0430(11) Uani 1 1 d . . .
H26A H 0.7562 -0.4476 0.3603 0.052 Uiso 1 1 calc R . .
H26B H 0.7213 -0.4597 0.4643 0.052 Uiso 1 1 calc R . .
C27 C 0.6332(4) 0.3231(3) 0.4638(4) 0.0577(14) Uani 1 1 d . . .
H27A H 0.6086 0.3787 0.4775 0.069 Uiso 1 1 calc R . .
C28 C 0.6252(4) 0.0842(3) 0.5511(4) 0.0444(12) Uani 1 1 d . . .
H28A H 0.6211 0.1003 0.6219 0.053 Uiso 1 1 calc R . .
H28B H 0.5537 0.0647 0.5046 0.053 Uiso 1 1 calc R . .
C29 C 0.8992(4) -0.0618(3) 0.3516(4) 0.0522(13) Uani 1 1 d . . .
H29A H 0.9698 -0.0455 0.3605 0.063 Uiso 1 1 calc R . .
C30 C 0.8156(4) -0.0401(4) 0.2569(4) 0.0549(14) Uani 1 1 d . . .
H30A H 0.8302 -0.0096 0.2011 0.066 Uiso 1 1 calc R . .
C32 C 0.6103(5) -0.3444(4) 0.2328(4) 0.0601(15) Uani 1 1 d . . .
H32A H 0.6730 -0.3102 0.2358 0.090 Uiso 1 1 calc R . .
H32B H 0.5466 -0.3087 0.2004 0.090 Uiso 1 1 calc R . .
H32C H 0.6061 -0.3973 0.1893 0.090 Uiso 1 1 calc R . .
C33 C 0.6888(5) 0.3153(4) 0.3919(4) 0.0583(14) Uani 1 1 d . . .
H33A H 0.6976 0.3656 0.3534 0.070 Uiso 1 1 calc R . .
C100 C 0.5228(4) -0.4286(3) 0.3486(4) 0.0577(14) Uani 1 1 d . . .
H10B H 0.4567 -0.3982 0.3085 0.087 Uiso 1 1 calc R . .
H10C H 0.5263 -0.4383 0.4228 0.087 Uiso 1 1 calc R . .
H10D H 0.5251 -0.4853 0.3143 0.087 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
O1 C9 1.362(5) . ?
O1 C28 1.440(5) . ?
O2 C4 1.449(5) . ?
O2 C23 1.461(5) . ?
O3 C20 1.370(5) . ?
C4 C14 1.507(6) . ?
C4 C6 1.544(5) . ?
N1 C25 1.372(6) . ?
N1 C8 1.378(6) . ?
N1 C17 1.457(6) . ?
C6 C22 1.508(6) . ?
C6 C12 1.542(6) . ?
C7 C15 1.368(6) . ?
C7 C10 1.396(6) . ?
C8 C11 1.417(6) . ?
C8 C15 1.407(6) . ?
C9 C11 1.411(6) . ?
C9 C10 1.382(6) . ?
C11 C22 1.448(6) . ?
C12 C20 1.387(6) . ?
C12 C21 1.390(6) . ?
C13 C16 1.377(6) . ?
C13 C18 1.405(6) . ?
C13 C28 1.491(6) . ?
C14 C26 1.546(6) . ?
C16 C27 1.380(7) . ?
C18 C24 1.393(6) . ?
C19 C20 1.397(6) . ?
C19 C30 1.379(7) . ?
C21 C29 1.400(6) . ?
C22 C25 1.359(6) . ?
C23 C32 1.523(6) . ?
C23 C26 1.542(6) . ?
C23 C100 1.526(6) . ?
C24 C33 1.351(7) . ?
C27 C33 1.377(7) . ?
C29 C30 1.375(7) . ?

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
C9 O1 C28 118.1(3) . . ?
C4 O2 C23 110.9(3) . . ?
O2 C4 C14 104.4(3) . . ?
O2 C4 C6 107.4(3) . . ?
C14 C4 C6 118.5(4) . . ?
C25 N1 C8 108.1(4) . . ?
C25 N1 C17 126.6(4) . . ?
C8 N1 C17 125.3(4) . . ?
C22 C6 C12 111.7(3) . . ?
C22 C6 C4 111.5(3) . . ?
C12 C6 C4 114.1(3) . . ?
C15 C7 C10 122.9(4) . . ?
N1 C8 C11 107.3(3) . . ?
N1 C8 C15 130.3(4) . . ?
C11 C8 C15 122.4(4) . . ?
O1 C9 C11 115.9(3) . . ?
O1 C9 C10 125.6(4) . . ?
C11 C9 C10 118.4(4) . . ?
C9 C10 C7 121.0(4) . . ?
C9 C11 C8 118.8(4) . . ?
C9 C11 C22 133.4(4) . . ?
C8 C11 C22 107.6(4) . . ?
C20 C12 C21 118.9(4) . . ?
C20 C12 C6 120.1(4) . . ?
C21 C12 C6 120.9(4) . . ?
C16 C13 C18 118.8(4) . . ?
C16 C13 C28 118.9(4) . . ?
C18 C13 C28 121.8(4) . . ?
C4 C14 C26 102.0(4) . . ?
C7 C15 C8 116.3(4) . . ?
C27 C16 C13 121.2(4) . . ?
C24 C18 C13 119.2(4) . . ?
C20 C19 C30 119.9(5) . . ?
C12 C20 O3 122.8(4) . . ?
C12 C20 C19 120.3(4) . . ?
O3 C20 C19 116.9(4) . . ?
C12 C21 C29 121.0(4) . . ?
C25 C22 C11 104.8(4) . . ?
C25 C22 C6 130.9(4) . . ?
C11 C22 C6 124.3(4) . . ?
O2 C23 C32 108.4(4) . . ?
O2 C23 C26 104.5(3) . . ?
C32 C23 C26 111.5(4) . . ?
O2 C23 C100 108.2(3) . . ?
C32 C23 C100 111.7(4) . . ?
C26 C23 C100 112.1(4) . . ?
C33 C24 C18 120.4(5) . . ?
C22 C25 N1 112.1(4) . . ?
C23 C26 C14 102.2(4) . . ?
C16 C27 C33 119.2(5) . . ?
O1 C28 C13 113.7(4) . . ?
C30 C29 C21 119.1(5) . . ?
C29 C30 C19 120.8(5) . . ?
C24 C33 C27 121.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.087
