# 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
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# 
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#  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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H16 N4 O'
_chemical_formula_weight         388.42

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                   7.3662(15)
_cell_length_b                   12.232(2)
_cell_length_c                   12.351(3)
_cell_angle_alpha                72.49(3)
_cell_angle_beta                 75.10(3)
_cell_angle_gamma                88.58(3)
_cell_volume                     1024.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9842
_exptl_absorpt_correction_T_max  0.9921
_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         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8015
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3603
_reflns_number_gt                1687
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.0867P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3603
_refine_ls_number_parameters     271
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1693
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002

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
C8 C 0.2049(3) 0.7335(2) 0.7081(3) 0.0456(7) Uani 1 1 d . . .
C9 C 0.1657(3) 0.8592(2) 0.6385(3) 0.0506(8) Uani 1 1 d . . .
H9 H 0.2867 0.9037 0.6084 0.061 Uiso 1 1 calc R . .
C13 C 0.0336(3) 0.6550(2) 0.7365(3) 0.0484(7) Uani 1 1 d . . .
H13 H -0.0219 0.6088 0.8126 0.058 Uiso 1 1 calc R . .
C12 C -0.0327(3) 0.6558(2) 0.6475(3) 0.0527(8) Uani 1 1 d . . .
H12 H -0.1417 0.6134 0.6566 0.063 Uiso 1 1 calc R . .
C21 C 0.2791(3) 0.6790(2) 0.5127(3) 0.0525(8) Uani 1 1 d . . .
C1 C 0.1728(4) 0.7064(2) 0.9342(3) 0.0542(7) Uani 1 1 d U . .
C14 C 0.0353(4) 0.9185(2) 0.7163(3) 0.0526(7) Uani 1 1 d . . .
C23 C 0.4002(4) 0.7371(2) 0.3950(3) 0.0589(8) Uani 1 1 d . . .
C7 C 0.2849(4) 0.7326(2) 0.8108(3) 0.0576(8) Uani 1 1 d U . .
C11 C 0.0796(3) 0.7299(2) 0.5302(3) 0.0525(8) Uani 1 1 d . . .
H11 H 0.0221 0.7272 0.4677 0.063 Uiso 1 1 calc R . .
C22 C 0.2558(4) 0.5567(3) 0.5202(3) 0.0596(8) Uani 1 1 d . . .
C25 C 0.4287(3) 0.5833(3) 0.6778(3) 0.0576(8) Uani 1 1 d . . .
C10 C 0.1030(4) 0.8537(2) 0.5313(3) 0.0561(8) Uani 1 1 d . . .
H10A H 0.1954 0.8964 0.4603 0.067 Uiso 1 1 calc R . .
H10B H -0.0158 0.8899 0.5316 0.067 Uiso 1 1 calc R . .
C20 C 0.3647(3) 0.6921(2) 0.6155(3) 0.0490(7) Uani 1 1 d . . .
C24 C 0.5295(4) 0.7759(2) 0.5628(3) 0.0587(8) Uani 1 1 d . . .
C19 C -0.1602(4) 0.9052(2) 0.7434(3) 0.0620(9) Uani 1 1 d . . .
H19 H -0.2151 0.8597 0.7107 0.074 Uiso 1 1 calc R . .
C2 C -0.0202(4) 0.7153(2) 0.9693(3) 0.0613(8) Uani 1 1 d . . .
H2 H -0.0889 0.7358 0.9133 0.074 Uiso 1 1 calc R . .
C6 C 0.2709(5) 0.6744(3) 1.0205(3) 0.0776(10) Uani 1 1 d . . .
H6 H 0.4002 0.6674 0.9991 0.093 Uiso 1 1 calc R . .
C15 C 0.1117(5) 0.9874(2) 0.7663(3) 0.0720(10) Uani 1 1 d . . .
H15 H 0.2417 0.9985 0.7491 0.086 Uiso 1 1 calc R . .
C18 C -0.2727(5) 0.9581(3) 0.8172(4) 0.0800(11) Uani 1 1 d . . .
H18 H -0.4029 0.9484 0.8341 0.096 Uiso 1 1 calc R . .
C3 C -0.1105(5) 0.6937(3) 1.0868(4) 0.0757(11) Uani 1 1 d . . .
H3 H -0.2399 0.7003 1.1093 0.091 Uiso 1 1 calc R . .
C4 C -0.0137(7) 0.6631(3) 1.1704(4) 0.0922(13) Uani 1 1 d . . .
H4 H -0.0761 0.6492 1.2494 0.111 Uiso 1 1 calc R . .
C16 C -0.0037(7) 1.0400(3) 0.8417(4) 0.0940(13) Uani 1 1 d . . .
H16 H 0.0490 1.0853 0.8754 0.113 Uiso 1 1 calc R . .
C5 C 0.1775(7) 0.6530(3) 1.1371(4) 0.0944(12) Uani 1 1 d . . .
H5 H 0.2442 0.6315 1.1940 0.113 Uiso 1 1 calc R . .
C17 C -0.1950(7) 1.0249(3) 0.8662(4) 0.1000(14) Uani 1 1 d . . .
H17 H -0.2724 1.0604 0.9164 0.120 Uiso 1 1 calc R . .
N4 N 0.2348(4) 0.4633(2) 0.5243(3) 0.0782(9) Uani 1 1 d . . .
N1 N 0.6526(3) 0.8418(2) 0.5134(3) 0.0777(9) Uani 1 1 d . . .
N3 N 0.4885(4) 0.7825(2) 0.3013(3) 0.0838(9) Uani 1 1 d . . .
N2 N 0.4732(4) 0.4981(2) 0.7307(3) 0.0821(10) Uani 1 1 d . . .
O1 O 0.4549(3) 0.7529(2) 0.7874(2) 0.0856(8) 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
C8 C13 1.505(3) . ?
C8 C7 1.527(4) . ?
C8 C9 1.581(3) . ?
C8 C20 1.605(4) . ?
C9 C14 1.511(4) . ?
C9 C10 1.530(4) . ?
C13 C12 1.310(4) . ?
C12 C11 1.495(4) . ?
C21 C23 1.469(4) . ?
C21 C22 1.483(4) . ?
C21 C11 1.571(4) . ?
C21 C20 1.604(4) . ?
C1 C2 1.387(4) . ?
C1 C6 1.394(5) . ?
C1 C7 1.476(4) . ?
C14 C15 1.386(4) . ?
C14 C19 1.394(4) . ?
C23 N3 1.147(4) . ?
C7 O1 1.225(3) . ?
C11 C10 1.533(4) . ?
C22 N4 1.140(4) . ?
C25 N2 1.142(3) . ?
C25 C20 1.458(4) . ?
C20 C24 1.484(4) . ?
C24 N1 1.140(3) . ?
C19 C18 1.371(5) . ?
C2 C3 1.379(5) . ?
C6 C5 1.374(5) . ?
C15 C16 1.389(5) . ?
C18 C17 1.364(6) . ?
C3 C4 1.359(6) . ?
C4 C5 1.376(5) . ?
C16 C17 1.368(6) . ?

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
C13 C8 C7 116.6(2) . . ?
C13 C8 C9 109.4(2) . . ?
C7 C8 C9 111.6(2) . . ?
C13 C8 C20 105.8(2) . . ?
C7 C8 C20 107.5(2) . . ?
C9 C8 C20 105.1(2) . . ?
C14 C9 C10 115.1(2) . . ?
C14 C9 C8 112.7(2) . . ?
C10 C9 C8 108.2(2) . . ?
C12 C13 C8 116.0(3) . . ?
C13 C12 C11 115.1(2) . . ?
C23 C21 C22 106.8(3) . . ?
C23 C21 C11 110.8(2) . . ?
C22 C21 C11 108.3(2) . . ?
C23 C21 C20 112.4(2) . . ?
C22 C21 C20 111.3(2) . . ?
C11 C21 C20 107.2(2) . . ?
C2 C1 C6 118.3(3) . . ?
C2 C1 C7 124.7(3) . . ?
C6 C1 C7 116.9(3) . . ?
C15 C14 C19 117.8(3) . . ?
C15 C14 C9 119.1(3) . . ?
C19 C14 C9 123.1(3) . . ?
N3 C23 C21 177.2(4) . . ?
O1 C7 C1 118.9(3) . . ?
O1 C7 C8 116.4(3) . . ?
C1 C7 C8 124.6(2) . . ?
C12 C11 C10 110.8(3) . . ?
C12 C11 C21 104.9(2) . . ?
C10 C11 C21 108.0(2) . . ?
N4 C22 C21 178.3(4) . . ?
N2 C25 C20 177.2(3) . . ?
C9 C10 C11 112.1(2) . . ?
C25 C20 C24 107.8(2) . . ?
C25 C20 C21 111.3(2) . . ?
C24 C20 C21 109.0(2) . . ?
C25 C20 C8 108.4(2) . . ?
C24 C20 C8 111.2(2) . . ?
C21 C20 C8 109.1(2) . . ?
N1 C24 C20 174.2(4) . . ?
C18 C19 C14 121.0(3) . . ?
C3 C2 C1 120.2(4) . . ?
C5 C6 C1 120.4(4) . . ?
C14 C15 C16 120.7(3) . . ?
C17 C18 C19 120.4(4) . . ?
C4 C3 C2 121.1(4) . . ?
C3 C4 C5 119.4(4) . . ?
C17 C16 C15 119.9(4) . . ?
C6 C5 C4 120.6(4) . . ?
C18 C17 C16 120.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 1014190'
