# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_l13_07
_database_code_depnum_ccdc_archive 'CCDC 1014399'
_audit_update_record             
;
2014-07-17 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 N'
_chemical_formula_weight         305.36

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'

_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   19.533(4)
_cell_length_b                   7.5052(15)
_cell_length_c                   21.247(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3114.9(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.075
_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      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  ?
_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            46038
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.42
_reflns_number_total             3545
_reflns_number_gt                1741
_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)+(0.0910P)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    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3545
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1671
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.000
_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 0.17061(9) 0.6715(2) 0.13160(8) 0.0605(5) Uani 1 1 d . . .
C18 C 0.12517(11) 0.8212(3) -0.09931(9) 0.0549(5) Uani 1 1 d . . .
C6 C 0.24397(10) 0.7225(3) 0.03908(9) 0.0518(5) Uani 1 1 d . . .
C23 C 0.18405(10) 0.7526(3) -0.06787(9) 0.0508(5) Uani 1 1 d . . .
C9 C 0.11633(11) 0.7111(3) 0.09752(9) 0.0551(5) Uani 1 1 d . . .
C22 C 0.23719(11) 0.6876(3) -0.10599(10) 0.0595(6) Uani 1 1 d . . .
H22 H 0.2747 0.6329 -0.0872 0.071 Uiso 1 1 calc R . .
C17 C 0.06534(11) 0.8603(3) -0.06395(10) 0.0603(6) Uani 1 1 d . . .
H17 H 0.0283 0.9144 -0.0837 0.072 Uiso 1 1 calc R . .
C8 C 0.11988(10) 0.7556(3) 0.03156(9) 0.0514(5) Uani 1 1 d . . .
C16 C 0.06153(11) 0.8197(3) -0.00165(10) 0.0573(6) Uani 1 1 d . . .
H16 H 0.0202 0.8340 0.0195 0.069 Uiso 1 1 calc R . .
C10 C 0.04951(11) 0.7078(3) 0.13187(9) 0.0564(5) Uani 1 1 d . . .
C19 C 0.12544(12) 0.8392(3) -0.16504(10) 0.0622(6) Uani 1 1 d . . .
H19 H 0.0877 0.8897 -0.1850 0.075 Uiso 1 1 calc R . .
C7 C 0.18305(10) 0.7417(3) 0.00032(10) 0.0513(5) Uani 1 1 d . . .
C5 C 0.31152(11) 0.7574(3) 0.01836(11) 0.0595(6) Uani 1 1 d . . .
H5 H 0.3189 0.7919 -0.0231 0.071 Uiso 1 1 calc R . .
C1 C 0.23393(11) 0.6840(3) 0.10350(10) 0.0581(6) Uani 1 1 d . . .
C13 C -0.07221(13) 0.7015(3) 0.20087(11) 0.0711(7) Uani 1 1 d . . .
H13 H -0.1127 0.6996 0.2239 0.085 Uiso 1 1 calc R . .
C20 C 0.17978(13) 0.7844(3) -0.20027(11) 0.0704(7) Uani 1 1 d . . .
H20 H 0.1800 0.8012 -0.2436 0.084 Uiso 1 1 calc R . .
C11 C 0.04369(12) 0.7963(3) 0.18934(9) 0.0599(6) Uani 1 1 d . . .
H11 H 0.0810 0.8588 0.2052 0.072 Uiso 1 1 calc R . .
C21 C 0.23492(12) 0.7029(3) -0.17037(10) 0.0675(6) Uani 1 1 d . . .
H21 H 0.2708 0.6582 -0.1944 0.081 Uiso 1 1 calc R . .
C2 C 0.29148(12) 0.6611(3) 0.14254(11) 0.0714(7) Uani 1 1 d . . .
H2 H 0.2852 0.6272 0.1842 0.086 Uiso 1 1 calc R . .
C12 C -0.01654(12) 0.7924(3) 0.22301(10) 0.0657(6) Uani 1 1 d . . .
H12 H -0.0194 0.8523 0.2612 0.079 Uiso 1 1 calc R . .
C15 C -0.00733(12) 0.6153(3) 0.11002(10) 0.0665(6) Uani 1 1 d . . .
H15 H -0.0047 0.5544 0.0720 0.080 Uiso 1 1 calc R . .
C14 C -0.06782(12) 0.6122(3) 0.14392(12) 0.0721(7) Uani 1 1 d . . .
H14 H -0.1055 0.5502 0.1285 0.086 Uiso 1 1 calc R . .
C4 C 0.36607(12) 0.7413(3) 0.05833(11) 0.0699(6) Uani 1 1 d . . .
H4 H 0.4100 0.7661 0.0440 0.084 Uiso 1 1 calc R . .
C3 C 0.35605(12) 0.6876(4) 0.12068(12) 0.0759(7) Uani 1 1 d . . .
H3 H 0.3934 0.6701 0.1471 0.091 Uiso 1 1 calc R . .


_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 C9 1.318(3) . ?
N1 C1 1.377(3) . ?
C18 C19 1.403(3) . ?
C18 C17 1.420(3) . ?
C18 C23 1.426(3) . ?
C6 C1 1.412(3) . ?
C6 C5 1.415(3) . ?
C6 C7 1.454(3) . ?
C23 C22 1.404(3) . ?
C23 C7 1.451(3) . ?
C9 C8 1.442(3) . ?
C9 C10 1.496(3) . ?
C22 C21 1.374(3) . ?
C17 C16 1.360(3) . ?
C8 C7 1.405(3) . ?
C8 C16 1.424(3) . ?
C10 C15 1.390(3) . ?
C10 C11 1.394(3) . ?
C19 C20 1.362(3) . ?
C5 C4 1.368(3) . ?
C1 C2 1.408(3) . ?
C13 C12 1.367(3) . ?
C13 C14 1.386(3) . ?
C20 C21 1.392(3) . ?
C11 C12 1.377(3) . ?
C2 C3 1.359(3) . ?
C15 C14 1.384(3) . ?
C4 C3 1.398(3) . ?

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
C9 N1 C1 117.97(17) . . ?
C19 C18 C17 120.64(19) . . ?
C19 C18 C23 119.9(2) . . ?
C17 C18 C23 119.37(19) . . ?
C1 C6 C5 117.96(18) . . ?
C1 C6 C7 117.08(18) . . ?
C5 C6 C7 124.62(19) . . ?
C22 C23 C18 116.83(18) . . ?
C22 C23 C7 124.47(19) . . ?
C18 C23 C7 118.51(19) . . ?
N1 C9 C8 123.20(19) . . ?
N1 C9 C10 115.48(18) . . ?
C8 C9 C10 121.32(18) . . ?
C21 C22 C23 121.4(2) . . ?
C16 C17 C18 120.90(19) . . ?
C7 C8 C16 119.59(18) . . ?
C7 C8 C9 118.94(18) . . ?
C16 C8 C9 121.42(19) . . ?
C17 C16 C8 120.9(2) . . ?
C15 C10 C11 117.7(2) . . ?
C15 C10 C9 122.86(18) . . ?
C11 C10 C9 119.39(19) . . ?
C20 C19 C18 121.4(2) . . ?
C8 C7 C23 118.64(18) . . ?
C8 C7 C6 117.29(17) . . ?
C23 C7 C6 124.05(18) . . ?
C4 C5 C6 121.1(2) . . ?
N1 C1 C2 116.97(19) . . ?
N1 C1 C6 123.99(18) . . ?
C2 C1 C6 119.0(2) . . ?
C12 C13 C14 119.5(2) . . ?
C19 C20 C21 119.0(2) . . ?
C12 C11 C10 121.0(2) . . ?
C22 C21 C20 121.1(2) . . ?
C3 C2 C1 121.5(2) . . ?
C13 C12 C11 120.7(2) . . ?
C14 C15 C10 121.1(2) . . ?
C15 C14 C13 119.9(2) . . ?
C5 C4 C3 120.3(2) . . ?
C2 C3 C4 119.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.42
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041
