# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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_a
#TrackingRef 'L3.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 N3 O'
_chemical_formula_weight         299.32

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 '

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                   10.969(5)
_cell_length_b                   7.342(5)
_cell_length_c                   36.533(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2942(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8603
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      26.62

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9745
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_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            19174
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0126
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         1.11
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2592
_reflns_number_gt                2346
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0741P)^2^+0.6153P] where P=(Fo^2^+2Fc^2^)/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         2592
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.119
_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 0.47650(10) 0.19273(16) 0.55973(3) 0.0452(3) Uani 1 1 d . . .
N2 N 0.35148(12) 0.29581(18) 0.38928(3) 0.0436(3) Uani 1 1 d . . .
C8 C 0.38145(12) 0.16082(19) 0.50050(4) 0.0359(3) Uani 1 1 d . . .
N3 N 0.29187(11) 0.05981(17) 0.55888(3) 0.0396(3) Uani 1 1 d U . .
C12 C 0.37090(13) 0.2412(2) 0.42593(4) 0.0382(4) Uani 1 1 d . . .
C9 C 0.47585(14) 0.2562(2) 0.48358(4) 0.0422(4) Uani 1 1 d . . .
H9 H 0.5427 0.2935 0.4973 0.051 Uiso 1 1 calc R . .
C11 C 0.27810(14) 0.1427(2) 0.44270(4) 0.0409(4) Uani 1 1 d . . .
H11 H 0.2111 0.1056 0.4290 0.049 Uiso 1 1 calc R . .
C7 C 0.37942(13) 0.1319(2) 0.53988(4) 0.0394(3) Uani 1 1 d U . .
C5 C 0.44473(14) 0.1554(2) 0.59541(4) 0.0406(4) Uani 1 1 d . . .
C13 C 0.47113(14) 0.2956(2) 0.44674(4) 0.0426(4) Uani 1 1 d . . .
H13 H 0.5349 0.3586 0.4357 0.051 Uiso 1 1 calc R . .
C14 C 0.43771(15) 0.2995(2) 0.36645(4) 0.0442(4) Uani 1 1 d . . .
H14 H 0.5146 0.2584 0.3732 0.053 Uiso 1 1 calc R . .
C6 C 0.33095(14) 0.0736(2) 0.59519(4) 0.0394(4) Uani 1 1 d . . .
C10 C 0.28418(13) 0.0997(2) 0.47923(4) 0.0387(4) Uani 1 1 d . . .
H10 H 0.2231 0.0295 0.4898 0.046 Uiso 1 1 calc R . .
C19 C 0.50289(18) 0.3418(3) 0.30201(5) 0.0589(5) Uani 1 1 d . . .
H19 H 0.5754 0.2813 0.3071 0.071 Uiso 1 1 calc R . .
C15 C 0.41726(15) 0.3688(2) 0.32906(4) 0.0438(4) Uani 1 1 d . . .
N1 N 0.37884(18) 0.4958(3) 0.25768(4) 0.0718(5) Uani 1 1 d . . .
C3 C 0.27554(16) 0.0240(2) 0.62785(4) 0.0494(4) Uani 1 1 d . . .
H3 H 0.1998 -0.0328 0.6283 0.059 Uiso 1 1 calc R . .
C4 C 0.50954(17) 0.1916(2) 0.62695(4) 0.0527(4) Uani 1 1 d . . .
H4 H 0.5866 0.2444 0.6265 0.063 Uiso 1 1 calc R . .
C16 C 0.31200(16) 0.4628(2) 0.31964(4) 0.0502(4) Uani 1 1 d . . .
H16 H 0.2520 0.4849 0.3371 0.060 Uiso 1 1 calc R . .
C1 C 0.45218(18) 0.1440(3) 0.65929(4) 0.0581(5) Uani 1 1 d . . .
H1 H 0.4913 0.1671 0.6814 0.070 Uiso 1 1 calc R . .
C17 C 0.29766(19) 0.5226(3) 0.28433(5) 0.0603(5) Uani 1 1 d . . .
H17 H 0.2267 0.5858 0.2786 0.072 Uiso 1 1 calc R . .
C2 C 0.33808(17) 0.0630(3) 0.65967(4) 0.0555(5) Uani 1 1 d . . .
H2 H 0.3026 0.0339 0.6820 0.067 Uiso 1 1 calc R . .
C18 C 0.4793(2) 0.4062(3) 0.26712(5) 0.0728(6) Uani 1 1 d . . .
H18 H 0.5375 0.3853 0.2491 0.087 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 0.0444(6) 0.0543(7) 0.0370(6) 0.0024(5) -0.0020(4) -0.0029(5)
N2 0.0488(7) 0.0454(7) 0.0365(7) 0.0007(6) 0.0002(6) 0.0015(6)
C8 0.0376(7) 0.0334(7) 0.0367(8) -0.0008(6) -0.0004(6) 0.0058(6)
N3 0.0420(7) 0.0407(7) 0.0361(7) 0.0000(5) -0.0024(5) 0.0011(5)
C12 0.0433(8) 0.0357(8) 0.0354(8) -0.0012(6) -0.0008(6) 0.0058(6)
C9 0.0381(8) 0.0474(9) 0.0410(8) -0.0005(7) -0.0052(6) -0.0015(7)
C11 0.0432(9) 0.0392(8) 0.0404(8) -0.0018(6) -0.0067(6) -0.0019(6)
C7 0.0432(8) 0.0382(8) 0.0369(8) -0.0007(6) -0.0023(6) 0.0066(6)
C5 0.0456(8) 0.0430(8) 0.0331(8) 0.0006(6) -0.0007(6) 0.0027(7)
C13 0.0397(8) 0.0468(9) 0.0413(9) 0.0016(7) 0.0032(6) -0.0022(7)
C14 0.0474(9) 0.0444(8) 0.0408(8) -0.0017(7) -0.0012(7) 0.0027(7)
C6 0.0426(8) 0.0386(8) 0.0371(8) -0.0002(6) 0.0003(6) 0.0056(6)
C10 0.0396(8) 0.0353(7) 0.0411(8) 0.0014(6) -0.0003(6) -0.0015(6)
C19 0.0628(11) 0.0654(12) 0.0486(10) 0.0034(9) 0.0095(8) 0.0053(9)
C15 0.0542(9) 0.0394(8) 0.0377(8) -0.0010(6) 0.0012(7) -0.0041(7)
N1 0.0998(14) 0.0720(11) 0.0437(9) 0.0100(8) -0.0002(8) 0.0004(10)
C3 0.0519(10) 0.0479(9) 0.0485(9) 0.0050(7) 0.0094(7) 0.0029(7)
C4 0.0562(10) 0.0575(10) 0.0443(10) -0.0004(8) -0.0091(7) -0.0047(8)
C16 0.0570(10) 0.0494(9) 0.0441(9) -0.0002(7) 0.0007(7) 0.0005(8)
C1 0.0755(12) 0.0622(11) 0.0365(9) -0.0026(8) -0.0078(8) 0.0056(9)
C17 0.0742(12) 0.0581(11) 0.0487(10) 0.0056(8) -0.0103(9) 0.0018(9)
C2 0.0709(12) 0.0572(11) 0.0385(9) 0.0063(7) 0.0097(8) 0.0115(9)
C18 0.0906(15) 0.0821(15) 0.0458(10) 0.0047(10) 0.0198(10) 0.0020(12)

_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 C7 1.3635(18) . ?
O1 C5 1.3769(17) . ?
N2 C14 1.261(2) . ?
N2 C12 1.4138(19) . ?
C8 C10 1.394(2) . ?
C8 C9 1.394(2) . ?
C8 C7 1.455(2) . ?
N3 C7 1.298(2) . ?
N3 C6 1.3975(18) . ?
C12 C11 1.391(2) . ?
C12 C13 1.395(2) . ?
C9 C13 1.378(2) . ?
C9 H9 0.9300 . ?
C11 C10 1.373(2) . ?
C11 H11 0.9300 . ?
C5 C4 1.380(2) . ?
C5 C6 1.385(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.475(2) . ?
C14 H14 0.9300 . ?
C6 C3 1.388(2) . ?
C10 H10 0.9300 . ?
C19 C15 1.378(2) . ?
C19 C18 1.384(3) . ?
C19 H19 0.9300 . ?
C15 C16 1.388(2) . ?
N1 C18 1.329(3) . ?
N1 C17 1.334(3) . ?
C3 C2 1.380(2) . ?
C3 H3 0.9300 . ?
C4 C1 1.383(2) . ?
C4 H4 0.9300 . ?
C16 C17 1.372(2) . ?
C16 H16 0.9300 . ?
C1 C2 1.386(3) . ?
C1 H1 0.9300 . ?
C17 H17 0.9300 . ?
C2 H2 0.9300 . ?
C18 H18 0.9300 . ?

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
C7 O1 C5 103.92(12) . . ?
C14 N2 C12 121.30(14) . . ?
C10 C8 C9 118.88(14) . . ?
C10 C8 C7 119.51(13) . . ?
C9 C8 C7 121.54(13) . . ?
C7 N3 C6 104.53(13) . . ?
C11 C12 C13 119.06(14) . . ?
C11 C12 N2 117.02(13) . . ?
C13 C12 N2 123.61(14) . . ?
C13 C9 C8 120.70(14) . . ?
C13 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C10 C11 C12 120.81(14) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
N3 C7 O1 115.28(13) . . ?
N3 C7 C8 126.87(13) . . ?
O1 C7 C8 117.79(13) . . ?
O1 C5 C4 128.46(15) . . ?
O1 C5 C6 107.98(12) . . ?
C4 C5 C6 123.56(14) . . ?
C9 C13 C12 120.12(14) . . ?
C9 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
N2 C14 C15 120.40(15) . . ?
N2 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C3 C6 C5 120.22(14) . . ?
C3 C6 N3 131.50(15) . . ?
C5 C6 N3 108.28(12) . . ?
C11 C10 C8 120.32(14) . . ?
C11 C10 H10 119.8 . . ?
C8 C10 H10 119.8 . . ?
C15 C19 C18 118.93(19) . . ?
C15 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C15 C16 117.43(15) . . ?
C19 C15 C14 120.74(16) . . ?
C16 C15 C14 121.83(15) . . ?
C18 N1 C17 115.90(16) . . ?
C2 C3 C6 116.89(16) . . ?
C2 C3 H3 121.6 . . ?
C6 C3 H3 121.6 . . ?
C5 C4 C1 115.49(17) . . ?
C5 C4 H4 122.3 . . ?
C1 C4 H4 122.3 . . ?
C17 C16 C15 119.18(16) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C4 C1 C2 121.85(16) . . ?
C4 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
N1 C17 C16 124.25(19) . . ?
N1 C17 H17 117.9 . . ?
C16 C17 H17 117.9 . . ?
C3 C2 C1 121.98(15) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
N1 C18 C19 124.30(18) . . ?
N1 C18 H18 117.9 . . ?
C19 C18 H18 117.9 . . ?

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
C14 N2 C12 C11 -143.96(16) . . . . ?
C14 N2 C12 C13 42.6(2) . . . . ?
C10 C8 C9 C13 2.4(2) . . . . ?
C7 C8 C9 C13 -174.45(14) . . . . ?
C13 C12 C11 C10 0.2(2) . . . . ?
N2 C12 C11 C10 -173.58(14) . . . . ?
C6 N3 C7 O1 0.72(17) . . . . ?
C6 N3 C7 C8 -176.35(14) . . . . ?
C5 O1 C7 N3 -0.65(17) . . . . ?
C5 O1 C7 C8 176.70(12) . . . . ?
C10 C8 C7 N3 -3.3(2) . . . . ?
C9 C8 C7 N3 173.55(14) . . . . ?
C10 C8 C7 O1 179.66(13) . . . . ?
C9 C8 C7 O1 -3.5(2) . . . . ?
C7 O1 C5 C4 -178.90(16) . . . . ?
C7 O1 C5 C6 0.28(16) . . . . ?
C8 C9 C13 C12 0.4(2) . . . . ?
C11 C12 C13 C9 -1.8(2) . . . . ?
N2 C12 C13 C9 171.61(14) . . . . ?
C12 N2 C14 C15 -175.84(13) . . . . ?
O1 C5 C6 C3 -178.90(14) . . . . ?
C4 C5 C6 C3 0.3(2) . . . . ?
O1 C5 C6 N3 0.12(17) . . . . ?
C4 C5 C6 N3 179.35(15) . . . . ?
C7 N3 C6 C3 178.37(16) . . . . ?
C7 N3 C6 C5 -0.49(16) . . . . ?
C12 C11 C10 C8 2.7(2) . . . . ?
C9 C8 C10 C11 -4.0(2) . . . . ?
C7 C8 C10 C11 172.99(14) . . . . ?
C18 C19 C15 C16 -1.0(3) . . . . ?
C18 C19 C15 C14 178.89(17) . . . . ?
N2 C14 C15 C19 -167.51(16) . . . . ?
N2 C14 C15 C16 12.4(2) . . . . ?
C5 C6 C3 C2 1.1(2) . . . . ?
N3 C6 C3 C2 -177.70(15) . . . . ?
O1 C5 C4 C1 177.74(15) . . . . ?
C6 C5 C4 C1 -1.3(3) . . . . ?
C19 C15 C16 C17 0.5(3) . . . . ?
C14 C15 C16 C17 -179.46(16) . . . . ?
C5 C4 C1 C2 1.0(3) . . . . ?
C18 N1 C17 C16 -0.5(3) . . . . ?
C15 C16 C17 N1 0.4(3) . . . . ?
C6 C3 C2 C1 -1.4(3) . . . . ?
C4 C1 C2 C3 0.4(3) . . . . ?
C17 N1 C18 C19 -0.1(3) . . . . ?
C15 C19 C18 N1 0.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.066


_database_code_depnum_ccdc_archive 'CCDC 933959'