# 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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1
#TrackingRef 'tpa-co.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 N O'
_chemical_formula_weight         349.41

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   Pca2(1)

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

_cell_length_a                   16.740(5)
_cell_length_b                   12.432(5)
_cell_length_c                   9.236(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1922.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10430
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3385
_reflns_number_gt                2353
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0438P)^2^+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0064(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_number_reflns         3385
_refine_ls_number_parameters     245
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.002
_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
N1 N 0.17539(9) -0.04509(12) 0.6834(2) 0.0608(5) Uani 1 1 d . . .
C2 C 0.18564(11) 0.06113(15) 0.6366(2) 0.0503(5) Uani 1 1 d . . .
C3 C 0.13321(11) 0.14281(15) 0.6796(2) 0.0532(5) Uani 1 1 d . . .
H3 H 0.0904 0.1263 0.7397 0.064 Uiso 1 1 calc R . .
C4 C 0.20807(12) 0.27514(14) 0.5466(2) 0.0515(5) Uani 1 1 d . . .
C5 C 0.21744(14) 0.38687(16) 0.4932(3) 0.0616(6) Uani 1 1 d . . .
C6 C 0.24885(12) 0.08845(14) 0.5456(2) 0.0526(5) Uani 1 1 d . . .
H6 H 0.2836 0.0354 0.5127 0.063 Uiso 1 1 calc R . .
C7 C 0.14415(11) 0.24678(16) 0.6344(2) 0.0544(5) Uani 1 1 d . . .
H7 H 0.1080 0.2994 0.6632 0.065 Uiso 1 1 calc R . .
C8 C 0.24062(13) -0.11950(15) 0.6868(2) 0.0568(5) Uani 1 1 d . . .
C9 C 0.25993(11) 0.19368(15) 0.5042(2) 0.0541(5) Uani 1 1 d . . .
H9 H 0.3035 0.2109 0.4461 0.065 Uiso 1 1 calc R . .
O1 O 0.15929(10) 0.44412(14) 0.4747(2) 0.0927(6) Uani 1 1 d . . .
C11 C 0.31093(12) -0.09370(19) 0.7545(3) 0.0678(7) Uani 1 1 d . . .
H11 H 0.3170 -0.0264 0.7971 0.081 Uiso 1 1 calc R . .
C12 C 0.29924(13) 0.42756(17) 0.4602(3) 0.0614(6) Uani 1 1 d . . .
C13 C 0.23226(16) -0.21926(17) 0.6231(3) 0.0799(8) Uani 1 1 d . . .
H13 H 0.1852 -0.2374 0.5754 0.096 Uiso 1 1 calc R . .
C14 C 0.09754(12) -0.08504(15) 0.7162(3) 0.0572(6) Uani 1 1 d . . .
C15 C 0.30918(16) 0.49995(18) 0.3479(3) 0.0742(7) Uani 1 1 d . . .
H15 H 0.2651 0.5215 0.2940 0.089 Uiso 1 1 calc R . .
C16 C 0.36490(15) 0.39919(18) 0.5414(3) 0.0806(8) Uani 1 1 d . . .
H16 H 0.3594 0.3515 0.6183 0.097 Uiso 1 1 calc R . .
C17 C 0.03458(13) -0.06500(18) 0.6235(3) 0.0723(7) Uani 1 1 d . . .
H17 H 0.0424 -0.0246 0.5400 0.087 Uiso 1 1 calc R . .
C18 C 0.08557(14) -0.14490(18) 0.8392(3) 0.0695(7) Uani 1 1 d . . .
H18 H 0.1278 -0.1580 0.9023 0.083 Uiso 1 1 calc R . .
C19 C 0.38327(19) 0.5403(2) 0.3150(4) 0.0955(9) Uani 1 1 d . . .
H19 H 0.3893 0.5875 0.2377 0.115 Uiso 1 1 calc R . .
C20 C 0.2950(2) -0.2923(2) 0.6313(4) 0.1070(12) Uani 1 1 d . . .
H20 H 0.2896 -0.3599 0.5895 0.128 Uiso 1 1 calc R . .
C21 C -0.05156(16) -0.1664(2) 0.7790(4) 0.0910(9) Uani 1 1 d . . .
H21 H -0.1018 -0.1942 0.8004 0.109 Uiso 1 1 calc R . .
C22 C 0.43914(17) 0.4416(2) 0.5086(4) 0.1037(10) Uani 1 1 d . . .
H22 H 0.4833 0.4225 0.5640 0.124 Uiso 1 1 calc R . .
C23 C -0.04026(14) -0.1055(2) 0.6558(4) 0.0871(8) Uani 1 1 d . . .
H23 H -0.0831 -0.0917 0.5944 0.105 Uiso 1 1 calc R . .
C24 C 0.01105(16) -0.1854(2) 0.8687(3) 0.0814(8) Uani 1 1 d . . .
H24 H 0.0033 -0.2266 0.9516 0.098 Uiso 1 1 calc R . .
C25 C 0.37275(16) -0.1673(3) 0.7599(3) 0.0904(9) Uani 1 1 d . . .
H25 H 0.4204 -0.1487 0.8052 0.109 Uiso 1 1 calc R . .
C26 C 0.3647(2) -0.2656(3) 0.7000(4) 0.1091(11) Uani 1 1 d . . .
H26 H 0.4063 -0.3151 0.7054 0.131 Uiso 1 1 calc R . .
C27 C 0.4480(2) 0.5112(2) 0.3956(4) 0.1052(10) Uani 1 1 d . . .
H27 H 0.4982 0.5388 0.3736 0.126 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
N1 0.0467(9) 0.0491(9) 0.0865(14) 0.0098(11) -0.0010(10) -0.0040(8)
C2 0.0448(11) 0.0491(12) 0.0571(14) -0.0006(10) -0.0047(10) -0.0049(9)
C3 0.0443(11) 0.0592(12) 0.0561(14) -0.0021(11) 0.0037(10) -0.0011(9)
C4 0.0539(12) 0.0492(12) 0.0514(13) -0.0019(10) -0.0035(11) 0.0006(9)
C5 0.0769(16) 0.0489(12) 0.0590(15) 0.0006(11) -0.0035(13) 0.0035(11)
C6 0.0502(11) 0.0478(11) 0.0597(14) -0.0032(10) 0.0008(11) 0.0000(10)
C7 0.0537(12) 0.0498(11) 0.0597(14) -0.0093(11) -0.0044(11) 0.0063(10)
C8 0.0623(13) 0.0481(11) 0.0601(15) 0.0042(11) 0.0067(12) 0.0019(10)
C9 0.0491(12) 0.0553(11) 0.0579(14) -0.0026(11) 0.0028(10) -0.0048(10)
O1 0.0865(11) 0.0712(10) 0.1205(15) 0.0251(11) 0.0019(12) 0.0182(10)
C11 0.0600(14) 0.0739(14) 0.0694(18) -0.0032(13) 0.0019(13) 0.0170(12)
C12 0.0783(16) 0.0464(12) 0.0596(15) -0.0023(11) -0.0062(13) -0.0089(12)
C13 0.1078(19) 0.0524(14) 0.0793(19) -0.0014(13) 0.0262(15) -0.0083(13)
C14 0.0536(13) 0.0490(12) 0.0689(17) 0.0022(12) 0.0001(11) -0.0076(10)
C15 0.0901(18) 0.0584(14) 0.0741(17) 0.0064(14) -0.0017(14) -0.0069(13)
C16 0.0853(18) 0.0746(16) 0.0818(19) 0.0117(14) -0.0216(16) -0.0199(14)
C17 0.0590(14) 0.0777(16) 0.0800(18) 0.0083(13) -0.0120(13) -0.0125(12)
C18 0.0642(15) 0.0697(14) 0.0745(18) 0.0066(15) 0.0045(13) -0.0040(12)
C19 0.116(2) 0.0735(17) 0.097(2) 0.0094(17) 0.013(2) -0.0210(17)
C20 0.168(3) 0.0488(14) 0.105(3) 0.0062(16) 0.063(3) 0.0139(19)
C21 0.0627(17) 0.0852(18) 0.125(3) -0.0136(19) 0.0203(19) -0.0242(14)
C22 0.087(2) 0.102(2) 0.122(3) 0.007(2) -0.0297(19) -0.0248(18)
C23 0.0583(15) 0.0993(19) 0.104(2) -0.0038(18) -0.0117(15) -0.0170(14)
C24 0.0796(18) 0.0710(16) 0.094(2) 0.0044(14) 0.0297(17) -0.0074(14)
C25 0.0832(18) 0.112(2) 0.0764(19) 0.0069(17) 0.0063(15) 0.0379(17)
C26 0.129(3) 0.096(2) 0.103(3) 0.027(2) 0.042(2) 0.052(2)
C27 0.097(2) 0.092(2) 0.126(3) 0.000(2) 0.008(2) -0.0356(19)

_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
N1 C2 1.400(2) . ?
N1 C14 1.427(2) . ?
N1 C8 1.431(2) . ?
C2 C6 1.394(3) . ?
C2 C3 1.400(3) . ?
C3 C7 1.371(3) . ?
C4 C7 1.388(3) . ?
C4 C9 1.390(3) . ?
C4 C5 1.482(3) . ?
C5 O1 1.218(2) . ?
C5 C12 1.491(3) . ?
C6 C9 1.375(3) . ?
C8 C11 1.371(3) . ?
C8 C13 1.380(3) . ?
C11 C25 1.382(3) . ?
C12 C16 1.376(3) . ?
C12 C15 1.383(3) . ?
C13 C20 1.391(4) . ?
C14 C18 1.373(3) . ?
C14 C17 1.380(3) . ?
C15 C19 1.372(3) . ?
C16 C22 1.384(3) . ?
C17 C23 1.383(3) . ?
C18 C24 1.373(3) . ?
C19 C27 1.364(4) . ?
C20 C26 1.369(4) . ?
C21 C24 1.357(4) . ?
C21 C23 1.379(4) . ?
C22 C27 1.363(4) . ?
C25 C26 1.349(4) . ?

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 N1 C14 120.37(15) . . ?
C2 N1 C8 121.52(16) . . ?
C14 N1 C8 117.84(15) . . ?
C6 C2 C3 118.07(17) . . ?
C6 C2 N1 120.60(17) . . ?
C3 C2 N1 121.33(17) . . ?
C7 C3 C2 120.93(18) . . ?
C7 C4 C9 117.44(17) . . ?
C7 C4 C5 120.92(18) . . ?
C9 C4 C5 121.53(19) . . ?
O1 C5 C4 120.6(2) . . ?
O1 C5 C12 120.47(19) . . ?
C4 C5 C12 118.88(19) . . ?
C9 C6 C2 120.11(18) . . ?
C3 C7 C4 121.36(18) . . ?
C11 C8 C13 119.5(2) . . ?
C11 C8 N1 120.91(18) . . ?
C13 C8 N1 119.6(2) . . ?
C6 C9 C4 122.04(19) . . ?
C8 C11 C25 120.3(2) . . ?
C16 C12 C15 118.6(2) . . ?
C16 C12 C5 122.4(2) . . ?
C15 C12 C5 119.0(2) . . ?
C8 C13 C20 119.1(3) . . ?
C18 C14 C17 120.0(2) . . ?
C18 C14 N1 119.8(2) . . ?
C17 C14 N1 120.2(2) . . ?
C19 C15 C12 120.9(3) . . ?
C12 C16 C22 120.0(3) . . ?
C14 C17 C23 119.5(3) . . ?
C24 C18 C14 119.7(2) . . ?
C27 C19 C15 120.0(3) . . ?
C26 C20 C13 120.8(3) . . ?
C24 C21 C23 119.6(2) . . ?
C27 C22 C16 120.5(3) . . ?
C21 C23 C17 120.1(3) . . ?
C21 C24 C18 121.1(3) . . ?
C26 C25 C11 120.7(3) . . ?
C25 C26 C20 119.6(3) . . ?
C22 C27 C19 119.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.099
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.026


_database_code_depnum_ccdc_archive 'CCDC 872836'