# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 N3 O2'
_chemical_formula_weight         395.45

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   15.7738(7)
_cell_length_b                   7.7296(4)
_cell_length_c                   17.0325(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.216(5)
_cell_angle_gamma                90.00
_cell_volume                     2013.11(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2239
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      28.84

_exptl_crystal_description       rod-like
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_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            8782
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         28.91
_reflns_number_total             4531
_reflns_number_gt                2916
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_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)+(0.0456P)²+0.0656P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4531
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.003

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
C1 C 0.96382(12) 0.3515(3) 0.74637(12) 0.0554(5) Uani 1 1 d . . .
H1 H 0.9769(11) 0.302(2) 0.7974(11) 0.061(6) Uiso 1 1 d . . .
C2 C 1.02113(13) 0.3632(3) 0.69770(13) 0.0618(5) Uani 1 1 d . . .
H2 H 1.0811(12) 0.317(2) 0.7157(11) 0.072(6) Uiso 1 1 d . . .
C3 C 0.99709(13) 0.4407(3) 0.62153(13) 0.0609(5) Uani 1 1 d . . .
H3 H 1.0395(12) 0.446(2) 0.5885(12) 0.068(6) Uiso 1 1 d . . .
C4 C 0.91360(12) 0.5058(2) 0.59148(12) 0.0521(5) Uani 1 1 d . . .
H4 H 0.8947(11) 0.564(2) 0.5350(11) 0.057(5) Uiso 1 1 d . . .
C5 C 0.85391(11) 0.4957(2) 0.63965(10) 0.0437(4) Uani 1 1 d . . .
C6 C 0.87965(11) 0.4190(2) 0.71692(10) 0.0462(4) Uani 1 1 d . . .
C7 C 0.73949(11) 0.4990(2) 0.70049(10) 0.0426(4) Uani 1 1 d . . .
C8 C 0.76342(10) 0.5458(2) 0.62875(9) 0.0415(4) Uani 1 1 d . . .
C9 C 0.70145(11) 0.6180(2) 0.56505(10) 0.0437(4) Uani 1 1 d . . .
H9 H 0.7166(10) 0.654(2) 0.5133(10) 0.051(5) Uiso 1 1 d . . .
C10 C 0.61585(10) 0.6468(2) 0.57214(10) 0.0416(4) Uani 1 1 d . . .
C11 C 0.59486(12) 0.6000(2) 0.64530(10) 0.0475(4) Uani 1 1 d . . .
H11 H 0.5374(11) 0.615(2) 0.6516(10) 0.051(5) Uiso 1 1 d . . .
C12 C 0.65484(12) 0.5268(2) 0.70921(11) 0.0477(4) Uani 1 1 d . . .
H12 H 0.6406(11) 0.493(2) 0.7591(11) 0.063(5) Uiso 1 1 d . . .
C13 C 0.55604(11) 0.7218(2) 0.50201(10) 0.0446(4) Uani 1 1 d . . .
H13 H 0.5850(10) 0.7414(19) 0.4601(10) 0.047(5) Uiso 1 1 d . . .
C14 C 0.47146(10) 0.7728(2) 0.48575(10) 0.0413(4) Uani 1 1 d . . .
C15 C 0.42087(11) 0.7555(2) 0.54484(11) 0.0551(5) Uani 1 1 d . . .
C16 C 0.42521(10) 0.8519(2) 0.40752(10) 0.0405(4) Uani 1 1 d . . .
C17 C 0.47035(12) 0.9028(2) 0.35014(11) 0.0526(5) Uani 1 1 d . . .
H17 H 0.5362(12) 0.884(2) 0.3621(11) 0.072(6) Uiso 1 1 d . . .
C18 C 0.42796(12) 0.9804(3) 0.27840(12) 0.0527(5) Uani 1 1 d . . .
H18 H 0.4597(12) 1.021(2) 0.2388(12) 0.070(6) Uiso 1 1 d . . .
C19 C 0.33903(10) 1.0069(2) 0.26266(10) 0.0422(4) Uani 1 1 d . . .
C20 C 0.29217(12) 0.9577(2) 0.31715(11) 0.0491(4) Uani 1 1 d . . .
H20 H 0.2312(12) 0.975(2) 0.3055(11) 0.062(5) Uiso 1 1 d . . .
C21 C 0.33537(11) 0.8827(2) 0.38915(11) 0.0484(4) Uani 1 1 d . . .
H21 H 0.3030(10) 0.850(2) 0.4260(10) 0.050(5) Uiso 1 1 d . . .
C22 C 0.81189(14) 0.3524(3) 0.83294(11) 0.0519(5) Uani 1 1 d . . .
H22A H 0.8477(12) 0.247(2) 0.8400(11) 0.066(6) Uiso 1 1 d . . .
H22B H 0.7516(13) 0.305(2) 0.8328(12) 0.074(6) Uiso 1 1 d . . .
C23 C 0.84263(16) 0.4794(3) 0.90177(11) 0.0580(5) Uani 1 1 d . . .
H23A H 0.8992(13) 0.535(2) 0.8957(12) 0.073(6) Uiso 1 1 d . . .
H23B H 0.7947(15) 0.573(3) 0.8996(14) 0.103(8) Uiso 1 1 d . . .
C24 C 0.85777(18) 0.3890(3) 0.98263(12) 0.0691(6) Uani 1 1 d . . .
H24A H 0.8079(16) 0.307(3) 0.9863(15) 0.114(9) Uiso 1 1 d . . .
H24B H 0.9103(16) 0.295(3) 0.9861(15) 0.116(9) Uiso 1 1 d . . .
C25 C 0.8830(2) 0.5076(4) 1.05486(15) 0.0859(8) Uani 1 1 d . . .
H25A H 0.9344(19) 0.582(4) 1.0450(17) 0.134(11) Uiso 1 1 d . . .
H25B H 0.8977(17) 0.441(3) 1.1089(19) 0.126(9) Uiso 1 1 d . . .
H25C H 0.829(2) 0.590(4) 1.0465(17) 0.136(11) Uiso 1 1 d . . .
N1 N 0.37880(11) 0.7462(3) 0.59055(11) 0.0857(6) Uani 1 1 d . . .
N2 N 0.80985(9) 0.42236(18) 0.75324(8) 0.0476(4) Uani 1 1 d . . .
N3 N 0.29465(10) 1.09111(18) 0.18667(9) 0.0504(4) Uani 1 1 d . . .
O1 O 0.33931(9) 1.16373(19) 0.14733(8) 0.0696(4) Uani 1 1 d . . .
O2 O 0.21499(9) 1.08693(19) 0.16583(9) 0.0798(5) Uani 1 1 d . . .


_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
C1 C2 1.371(3) . ?
C1 C6 1.400(2) . ?
C2 C3 1.394(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.395(2) . ?
C5 C6 1.409(2) . ?
C5 C8 1.446(2) . ?
C6 N2 1.389(2) . ?
C7 N2 1.379(2) . ?
C7 C12 1.396(2) . ?
C7 C8 1.412(2) . ?
C8 C9 1.387(2) . ?
C9 C10 1.403(2) . ?
C10 C11 1.413(2) . ?
C10 C13 1.449(2) . ?
C11 C12 1.376(2) . ?
C13 C14 1.353(2) . ?
C14 C15 1.436(2) . ?
C14 C16 1.485(2) . ?
C15 N1 1.143(2) . ?
C16 C21 1.395(2) . ?
C16 C17 1.399(2) . ?
C17 C18 1.378(3) . ?
C18 C19 1.377(2) . ?
C19 C20 1.375(2) . ?
C19 N3 1.464(2) . ?
C20 C21 1.376(2) . ?
C22 N2 1.454(2) . ?
C22 C23 1.515(3) . ?
C23 C24 1.510(3) . ?
C24 C25 1.507(3) . ?
N3 O2 1.2195(17) . ?
N3 O1 1.2215(17) . ?

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
C2 C1 C6 117.84(19) . . ?
C1 C2 C3 121.44(19) . . ?
C4 C3 C2 121.10(19) . . ?
C3 C4 C5 118.71(18) . . ?
C4 C5 C6 119.44(16) . . ?
C4 C5 C8 134.20(16) . . ?
C6 C5 C8 106.34(14) . . ?
N2 C6 C1 129.28(17) . . ?
N2 C6 C5 109.26(14) . . ?
C1 C6 C5 121.45(17) . . ?
N2 C7 C12 129.41(16) . . ?
N2 C7 C8 109.30(14) . . ?
C12 C7 C8 121.26(16) . . ?
C9 C8 C7 119.55(15) . . ?
C9 C8 C5 133.79(15) . . ?
C7 C8 C5 106.60(14) . . ?
C8 C9 C10 120.33(15) . . ?
C9 C10 C11 118.32(16) . . ?
C9 C10 C13 115.99(14) . . ?
C11 C10 C13 125.68(15) . . ?
C12 C11 C10 122.58(17) . . ?
C11 C12 C7 117.95(16) . . ?
C14 C13 C10 134.03(16) . . ?
C13 C14 C15 121.28(16) . . ?
C13 C14 C16 123.10(15) . . ?
C15 C14 C16 115.61(14) . . ?
N1 C15 C14 177.6(2) . . ?
C21 C16 C17 117.29(16) . . ?
C21 C16 C14 121.32(15) . . ?
C17 C16 C14 121.36(15) . . ?
C18 C17 C16 121.50(17) . . ?
C19 C18 C17 119.12(17) . . ?
C20 C19 C18 121.21(17) . . ?
C20 C19 N3 120.02(15) . . ?
C18 C19 N3 118.77(15) . . ?
C19 C20 C21 119.18(17) . . ?
C20 C21 C16 121.69(17) . . ?
N2 C22 C23 114.26(16) . . ?
C24 C23 C22 110.78(17) . . ?
C25 C24 C23 114.5(2) . . ?
C7 N2 C6 108.49(14) . . ?
C7 N2 C22 126.72(15) . . ?
C6 N2 C22 124.77(15) . . ?
O2 N3 O1 122.97(16) . . ?
O2 N3 C19 118.71(15) . . ?
O1 N3 C19 118.31(15) . . ?

_diffrn_measured_fraction_theta_max 0.852
_diffrn_reflns_theta_full        26.85
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.033
_database_code_depnum_ccdc_archive 'CCDC 993696'
