# 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.
#
data_o+pbca

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          400-402
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H21 N O3'
_chemical_formula_weight         395.44

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           Orthorhombic
_symmetry_space_group_name_H-M   'Pbca '
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4208(15)
_cell_length_b                   19.207(4)
_cell_length_c                   29.746(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4239.7(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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  'Stoe IPDS-II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15918
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_sigmaI/netI    0.1458
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3729
_reflns_number_gt                1195
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2005)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0638P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3729
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1727
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   0.724
_refine_ls_restrained_S_all      0.724
_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
C2 C 0.9062(5) 0.3526(2) 0.02062(13) 0.143(3) Uani 1 1 d G . .
C3 C 0.9065(5) 0.2823(3) 0.00960(8) 0.135(2) Uani 1 1 d G . .
H3 H 0.9267 0.2685 -0.0199 0.162 Uiso 1 1 calc R . .
C4 C 0.8764(4) 0.23261(17) 0.04273(11) 0.1115(18) Uani 1 1 d G . .
H4 H 0.8766 0.1856 0.0354 0.134 Uiso 1 1 calc R . .
C5 C 0.8461(4) 0.25323(15) 0.08688(10) 0.0732(11) Uani 1 1 d G . .
C6 C 0.8459(4) 0.32356(17) 0.09790(10) 0.0956(15) Uani 1 1 d G . .
H6 H 0.8256 0.3374 0.1274 0.115 Uiso 1 1 calc R . .
C7 C 0.8759(5) 0.37326(14) 0.06478(15) 0.132(2) Uani 1 1 d G . .
H7 H 0.8758 0.4203 0.0721 0.158 Uiso 1 1 calc R . .
C1 C 0.9549(10) 0.3912(4) -0.0469(2) 0.217(5) Uani 1 1 d . . .
H1A H 0.9723 0.4280 -0.0683 0.326 Uiso 1 1 calc R . .
H1B H 0.8512 0.3642 -0.0553 0.326 Uiso 1 1 calc R . .
H1C H 1.0594 0.3617 -0.0465 0.326 Uiso 1 1 calc R . .
C8 C 0.8212(5) 0.20112(18) 0.12342(13) 0.0602(10) Uani 1 1 d . . .
C9 C 0.8987(7) 0.1335(2) 0.11592(15) 0.0908(15) Uani 1 1 d . . .
C10 C 0.7501(5) 0.21702(17) 0.16330(13) 0.0580(10) Uani 1 1 d . . .
H10 H 0.7061 0.2621 0.1663 0.070 Uiso 1 1 calc R . .
C11 C 0.7326(5) 0.17265(16) 0.20289(12) 0.0529(9) Uani 1 1 d . . .
C12 C 0.6690(5) 0.09968(16) 0.19628(12) 0.0520(9) Uani 1 1 d . . .
C13 C 0.5270(5) 0.08525(17) 0.16742(12) 0.0616(11) Uani 1 1 d . . .
H13 H 0.4764 0.1208 0.1504 0.074 Uiso 1 1 calc R . .
C14 C 0.4603(6) 0.01841(19) 0.16387(13) 0.0695(11) Uani 1 1 d . . .
H14 H 0.3624 0.0097 0.1452 0.083 Uiso 1 1 calc R . .
C15 C 0.5366(6) -0.03524(19) 0.18755(14) 0.0718(12) Uani 1 1 d . . .
H15 H 0.4913 -0.0802 0.1848 0.086 Uiso 1 1 calc R . .
C16 C 0.6803(6) -0.02213(18) 0.21528(14) 0.0714(12) Uani 1 1 d . . .
H16 H 0.7340 -0.0586 0.2309 0.086 Uiso 1 1 calc R . .
C17 C 0.7460(6) 0.04474(17) 0.22025(11) 0.0618(10) Uani 1 1 d . . .
H17 H 0.8420 0.0532 0.2396 0.074 Uiso 1 1 calc R . .
C18 C 0.7650(5) 0.19670(16) 0.24432(13) 0.0574(10) Uani 1 1 d . . .
H18 H 0.7435 0.1664 0.2681 0.069 Uiso 1 1 calc R . .
C19 C 0.8319(5) 0.26694(17) 0.25564(14) 0.0586(10) Uani 1 1 d . . .
C20 C 0.8372(5) 0.29131(17) 0.30325(13) 0.0557(9) Uani 1 1 d . . .
C21 C 0.9137(5) 0.35515(18) 0.31258(14) 0.0654(11) Uani 1 1 d . . .
H21 H 0.9608 0.3814 0.2891 0.078 Uiso 1 1 calc R . .
C22 C 0.9224(6) 0.38104(19) 0.35565(16) 0.0725(12) Uani 1 1 d . . .
H22 H 0.9722 0.4247 0.3610 0.087 Uiso 1 1 calc R . .
C23 C 0.8572(6) 0.3422(2) 0.39058(15) 0.0732(12) Uani 1 1 d . . .
C24 C 0.7806(5) 0.2775(2) 0.38214(15) 0.0750(12) Uani 1 1 d . . .
H24 H 0.7364 0.2509 0.4058 0.090 Uiso 1 1 calc R . .
C25 C 0.7701(5) 0.25289(18) 0.33899(14) 0.0649(11) Uani 1 1 d . . .
H25 H 0.7172 0.2098 0.3336 0.078 Uiso 1 1 calc R . .
C26 C 0.9070(7) 0.4304(2) 0.44658(16) 0.1211(19) Uani 1 1 d . . .
H26A H 0.9002 0.4360 0.4786 0.182 Uiso 1 1 calc R . .
H26B H 0.8265 0.4627 0.4323 0.182 Uiso 1 1 calc R . .
H26C H 1.0281 0.4392 0.4367 0.182 Uiso 1 1 calc R . .
N1 N 0.9632(8) 0.0816(2) 0.10820(15) 0.153(2) Uani 1 1 d . . .
O1 O 0.9308(7) 0.4169(2) -0.00835(17) 0.1772(18) Uani 1 1 d . . .
O2 O 0.8854(4) 0.30586(12) 0.22565(9) 0.0777(8) Uani 1 1 d . . .
O3 O 0.8569(4) 0.36107(16) 0.43486(10) 0.1011(10) Uani 1 1 d . . .


_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
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C2 O1 1.516(5) . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 C8 1.489(4) . ?
C6 C7 1.3900 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C1 O1 1.261(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C8 C10 1.334(5) . ?
C8 C9 1.438(6) . ?
C9 N1 1.128(5) . ?
C10 C11 1.459(4) . ?
C10 H10 0.9300 . ?
C11 C18 1.338(5) . ?
C11 C12 1.492(4) . ?
C12 C13 1.387(5) . ?
C12 C17 1.396(4) . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.476(4) . ?
C18 H18 0.9300 . ?
C19 O2 1.230(4) . ?
C19 C20 1.492(5) . ?
C20 C21 1.380(4) . ?
C20 C25 1.387(5) . ?
C21 C22 1.376(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.367(5) . ?
C22 H22 0.9300 . ?
C23 O3 1.366(4) . ?
C23 C24 1.390(5) . ?
C24 C25 1.370(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 O3 1.426(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C3 C2 C7 120.0 . . ?
C3 C2 O1 131.1(4) . . ?
C7 C2 O1 108.9(4) . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C8 118.7(3) . . ?
C4 C5 C8 121.2(3) . . ?
C5 C6 C7 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C10 C8 C9 120.2(3) . . ?
C10 C8 C5 123.0(3) . . ?
C9 C8 C5 116.4(4) . . ?
N1 C9 C8 176.7(5) . . ?
C8 C10 C11 128.3(3) . . ?
C8 C10 H10 115.9 . . ?
C11 C10 H10 115.9 . . ?
C18 C11 C10 121.7(3) . . ?
C18 C11 C12 120.2(3) . . ?
C10 C11 C12 118.1(3) . . ?
C13 C12 C17 118.4(3) . . ?
C13 C12 C11 120.6(3) . . ?
C17 C12 C11 120.9(3) . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 119.5(4) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.6(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 120.2(4) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
C11 C18 C19 125.9(3) . . ?
C11 C18 H18 117.1 . . ?
C19 C18 H18 117.1 . . ?
O2 C19 C18 119.9(4) . . ?
O2 C19 C20 119.3(3) . . ?
C18 C19 C20 120.8(3) . . ?
C21 C20 C25 117.8(4) . . ?
C21 C20 C19 118.7(3) . . ?
C25 C20 C19 123.5(3) . . ?
C22 C21 C20 121.8(4) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C23 C22 C21 119.6(4) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
O3 C23 C22 126.1(4) . . ?
O3 C23 C24 114.2(4) . . ?
C22 C23 C24 119.7(4) . . ?
C25 C24 C23 120.1(4) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C20 120.9(4) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?
O3 C26 H26A 109.5 . . ?
O3 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O3 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 O1 C2 102.4(5) . . ?
C23 O3 C26 118.9(4) . . ?

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
C7 C2 C3 C4 0.0 . . . . ?
O1 C2 C3 C4 -178.5(4) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C3 C4 C5 C8 -177.4(3) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C8 C5 C6 C7 177.5(3) . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
O1 C2 C7 C6 178.8(3) . . . . ?
C6 C5 C8 C10 19.2(5) . . . . ?
C4 C5 C8 C10 -163.4(3) . . . . ?
C6 C5 C8 C9 -153.2(3) . . . . ?
C4 C5 C8 C9 24.2(5) . . . . ?
C9 C8 C10 C11 -2.2(6) . . . . ?
C5 C8 C10 C11 -174.3(3) . . . . ?
C8 C10 C11 C18 138.7(4) . . . . ?
C8 C10 C11 C12 -44.0(6) . . . . ?
C18 C11 C12 C13 134.3(4) . . . . ?
C10 C11 C12 C13 -43.1(5) . . . . ?
C18 C11 C12 C17 -43.2(5) . . . . ?
C10 C11 C12 C17 139.4(3) . . . . ?
C17 C12 C13 C14 2.2(5) . . . . ?
C11 C12 C13 C14 -175.3(3) . . . . ?
C12 C13 C14 C15 -2.2(6) . . . . ?
C13 C14 C15 C16 0.4(6) . . . . ?
C14 C15 C16 C17 1.4(6) . . . . ?
C15 C16 C17 C12 -1.3(6) . . . . ?
C13 C12 C17 C16 -0.5(5) . . . . ?
C11 C12 C17 C16 177.1(4) . . . . ?
C10 C11 C18 C19 -4.1(6) . . . . ?
C12 C11 C18 C19 178.6(3) . . . . ?
C11 C18 C19 O2 -9.7(6) . . . . ?
C11 C18 C19 C20 170.9(4) . . . . ?
O2 C19 C20 C21 -4.5(5) . . . . ?
C18 C19 C20 C21 175.0(3) . . . . ?
O2 C19 C20 C25 176.0(4) . . . . ?
C18 C19 C20 C25 -4.5(5) . . . . ?
C25 C20 C21 C22 -0.8(6) . . . . ?
C19 C20 C21 C22 179.7(4) . . . . ?
C20 C21 C22 C23 1.5(6) . . . . ?
C21 C22 C23 O3 179.9(4) . . . . ?
C21 C22 C23 C24 -1.0(6) . . . . ?
O3 C23 C24 C25 179.0(4) . . . . ?
C22 C23 C24 C25 -0.2(6) . . . . ?
C23 C24 C25 C20 0.8(6) . . . . ?
C21 C20 C25 C24 -0.4(6) . . . . ?
C19 C20 C25 C24 179.1(4) . . . . ?
C3 C2 O1 C1 -0.7(7) . . . . ?
C7 C2 O1 C1 -179.4(5) . . . . ?
C22 C23 O3 C26 8.5(6) . . . . ?
C24 C23 O3 C26 -170.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 995679'
