# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ddds67
_database_code_depnum_ccdc_archive 'CCDC 931269'
_audit_update_record             
;
2013-03-27 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_0_Damir_1364365787.UCL358_ddds67.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H17 N'
_chemical_formula_sum            'C24 H17 N'
_chemical_formula_weight         319.39

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   13.0849(4)
_cell_length_b                   9.1297(2)
_cell_length_c                   13.5767(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.893(3)
_cell_angle_gamma                90.00
_cell_volume                     1618.15(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3273
_cell_measurement_theta_min      3.0016
_cell_measurement_theta_max      25.2990

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_min  0.84618
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '180 images, ΔΦ 1.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10334
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2953
_reflns_number_gt                2157
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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)+(0.0439P)²+0.6451P] where P=(Fo²+2Fc²)/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         2953
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
C1 C 0.09425(14) 0.4085(2) 0.17854(13) 0.0309(4) Uani 1 1 d . . .
C2 C -0.00919(14) 0.43834(19) 0.14974(13) 0.0286(4) Uani 1 1 d . . .
C3 C -0.06914(14) 0.5461(2) 0.19789(13) 0.0314(4) Uani 1 1 d . . .
H3 H -0.0390 0.5975 0.2534 0.038 Uiso 1 1 calc R . .
C4 C -0.16666(14) 0.5759(2) 0.16616(13) 0.0327(4) Uani 1 1 d . . .
H4 H -0.2032 0.6483 0.1996 0.039 Uiso 1 1 calc R . .
C5 C -0.21712(14) 0.5015(2) 0.08336(13) 0.0310(4) Uani 1 1 d . . .
C6 C -0.31660(14) 0.5357(2) 0.04758(14) 0.0371(5) Uani 1 1 d . . .
H6 H -0.3546 0.6071 0.0805 0.044 Uiso 1 1 calc R . .
C7 C -0.36052(15) 0.4662(2) -0.03595(15) 0.0414(5) Uani 1 1 d . . .
H7 H -0.4279 0.4918 -0.0604 0.050 Uiso 1 1 calc R . .
C8 C -0.30709(15) 0.3602(2) -0.08377(15) 0.0408(5) Uani 1 1 d . . .
H8 H -0.3383 0.3135 -0.1407 0.049 Uiso 1 1 calc R . .
C9 C -0.20793(15) 0.3209(2) -0.04961(14) 0.0349(5) Uani 1 1 d . . .
C10 C -0.14930(16) 0.2117(2) -0.09763(15) 0.0408(5) Uani 1 1 d . . .
H10 H -0.1797 0.1612 -0.1533 0.049 Uiso 1 1 calc R . .
C11 C -0.05251(16) 0.1796(2) -0.06535(15) 0.0397(5) Uani 1 1 d . . .
H11 H -0.0164 0.1063 -0.0985 0.048 Uiso 1 1 calc R . .
C12 C -0.00250(14) 0.25312(19) 0.01757(14) 0.0332(4) Uani 1 1 d . . .
C13 C 0.09983(15) 0.2269(2) 0.04889(14) 0.0360(5) Uani 1 1 d . . .
H13 H 0.1376 0.1551 0.0161 0.043 Uiso 1 1 calc R . .
C14 C 0.14657(14) 0.3035(2) 0.12643(14) 0.0340(5) Uani 1 1 d . . .
H14 H 0.2166 0.2846 0.1452 0.041 Uiso 1 1 calc R . .
C15 C -0.05788(14) 0.36075(19) 0.06825(13) 0.0292(4) Uani 1 1 d . . .
C16 C -0.16106(14) 0.39334(19) 0.03452(13) 0.0294(4) Uani 1 1 d . . .
C17 C 0.15115(14) 0.4894(2) 0.25885(14) 0.0344(5) Uani 1 1 d . . .
H17 H 0.1259 0.5812 0.2794 0.041 Uiso 1 1 calc R . .
N18 N 0.23292(12) 0.43888(19) 0.30084(12) 0.0390(4) Uani 1 1 d . . .
C19 C 0.28961(15) 0.5296(3) 0.37425(15) 0.0455(5) Uani 1 1 d . . .
H19A H 0.2801 0.4905 0.4410 0.055 Uiso 1 1 calc R . .
H19B H 0.2619 0.6306 0.3710 0.055 Uiso 1 1 calc R . .
C20 C 0.40255(15) 0.5334(2) 0.35762(14) 0.0341(4) Uani 1 1 d . . .
C21 C 0.46554(15) 0.6317(2) 0.41062(15) 0.0395(5) Uani 1 1 d . . .
H21 H 0.4368 0.6969 0.4558 0.047 Uiso 1 1 calc R . .
C22 C 0.56944(16) 0.6363(2) 0.39869(16) 0.0429(5) Uani 1 1 d . . .
H22 H 0.6116 0.7038 0.4360 0.051 Uiso 1 1 calc R . .
C23 C 0.61227(16) 0.5435(2) 0.33305(16) 0.0430(5) Uani 1 1 d . . .
H23 H 0.6838 0.5468 0.3248 0.052 Uiso 1 1 calc R . .
C24 C 0.55090(15) 0.4461(2) 0.27962(15) 0.0429(5) Uani 1 1 d . . .
H24 H 0.5800 0.3825 0.2338 0.052 Uiso 1 1 calc R . .
C25 C 0.44691(15) 0.4400(2) 0.29199(15) 0.0403(5) Uani 1 1 d . . .
H25 H 0.4054 0.3712 0.2552 0.048 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
C1 C14 1.398(3) . ?
C1 C2 1.410(2) . ?
C1 C17 1.476(3) . ?
C2 C15 1.427(3) . ?
C2 C3 1.442(2) . ?
C3 C4 1.346(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.435(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 C16 1.421(3) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(3) . ?
C8 H8 0.9500 . ?
C9 C16 1.422(3) . ?
C9 C10 1.441(3) . ?
C10 C11 1.344(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.430(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(3) . ?
C12 C15 1.425(2) . ?
C13 C14 1.373(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.427(2) . ?
C17 N18 1.265(2) . ?
C17 H17 0.9500 . ?
N18 C19 1.459(3) . ?
C19 C20 1.510(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.386(3) . ?
C20 C25 1.389(3) . ?
C21 C22 1.381(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.372(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
C14 C1 C2 119.09(17) . . ?
C14 C1 C17 118.50(17) . . ?
C2 C1 C17 122.33(16) . . ?
C1 C2 C15 119.26(16) . . ?
C1 C2 C3 123.20(17) . . ?
C15 C2 C3 117.53(16) . . ?
C4 C3 C2 121.68(18) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 122.06(17) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C16 119.53(18) . . ?
C6 C5 C4 122.40(17) . . ?
C16 C5 C4 118.02(16) . . ?
C7 C6 C5 120.44(19) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 120.61(19) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.86(19) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C16 119.21(18) . . ?
C8 C9 C10 122.64(19) . . ?
C16 C9 C10 118.13(18) . . ?
C11 C10 C9 121.46(19) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 121.69(18) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C15 118.62(18) . . ?
C13 C12 C11 122.46(17) . . ?
C15 C12 C11 118.88(18) . . ?
C14 C13 C12 120.91(17) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C1 121.98(18) . . ?
C13 C14 H14 119.0 . . ?
C1 C14 H14 119.0 . . ?
C12 C15 C2 120.11(17) . . ?
C12 C15 C16 119.31(17) . . ?
C2 C15 C16 120.54(16) . . ?
C5 C16 C9 119.33(17) . . ?
C5 C16 C15 120.15(17) . . ?
C9 C16 C15 120.50(17) . . ?
N18 C17 C1 121.29(18) . . ?
N18 C17 H17 119.4 . . ?
C1 C17 H17 119.4 . . ?
C17 N18 C19 118.42(18) . . ?
N18 C19 C20 111.59(17) . . ?
N18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
N18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C21 C20 C25 118.09(18) . . ?
C21 C20 C19 119.37(18) . . ?
C25 C20 C19 122.52(18) . . ?
C22 C21 C20 120.93(19) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 120.34(19) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 119.45(19) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 120.5(2) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 120.70(19) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?

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 C1 C2 C15 0.0(2) . . . . ?
C17 C1 C2 C15 176.91(16) . . . . ?
C14 C1 C2 C3 -179.04(16) . . . . ?
C17 C1 C2 C3 -2.2(3) . . . . ?
C1 C2 C3 C4 177.46(17) . . . . ?
C15 C2 C3 C4 -1.6(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -177.33(18) . . . . ?
C3 C4 C5 C16 0.1(3) . . . . ?
C16 C5 C6 C7 -0.8(3) . . . . ?
C4 C5 C6 C7 176.60(18) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C16 -1.2(3) . . . . ?
C7 C8 C9 C10 -179.57(18) . . . . ?
C8 C9 C10 C11 177.51(19) . . . . ?
C16 C9 C10 C11 -0.9(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C13 -176.47(18) . . . . ?
C10 C11 C12 C15 1.4(3) . . . . ?
C15 C12 C13 C14 -0.4(3) . . . . ?
C11 C12 C13 C14 177.45(17) . . . . ?
C12 C13 C14 C1 1.2(3) . . . . ?
C2 C1 C14 C13 -1.0(3) . . . . ?
C17 C1 C14 C13 -178.01(17) . . . . ?
C13 C12 C15 C2 -0.6(2) . . . . ?
C11 C12 C15 C2 -178.49(16) . . . . ?
C13 C12 C15 C16 177.31(16) . . . . ?
C11 C12 C15 C16 -0.6(2) . . . . ?
C1 C2 C15 C12 0.8(2) . . . . ?
C3 C2 C15 C12 179.87(15) . . . . ?
C1 C2 C15 C16 -177.11(15) . . . . ?
C3 C2 C15 C16 2.0(2) . . . . ?
C6 C5 C16 C9 -0.6(3) . . . . ?
C4 C5 C16 C9 -178.10(16) . . . . ?
C6 C5 C16 C15 177.81(16) . . . . ?
C4 C5 C16 C15 0.3(2) . . . . ?
C8 C9 C16 C5 1.6(3) . . . . ?
C10 C9 C16 C5 -179.96(16) . . . . ?
C8 C9 C16 C15 -176.84(16) . . . . ?
C10 C9 C16 C15 1.6(3) . . . . ?
C12 C15 C16 C5 -179.28(16) . . . . ?
C2 C15 C16 C5 -1.4(2) . . . . ?
C12 C15 C16 C9 -0.9(2) . . . . ?
C2 C15 C16 C9 177.00(16) . . . . ?
C14 C1 C17 N18 -21.6(3) . . . . ?
C2 C1 C17 N18 161.47(17) . . . . ?
C1 C17 N18 C19 175.24(16) . . . . ?
C17 N18 C19 C20 -132.78(19) . . . . ?
N18 C19 C20 C21 170.11(18) . . . . ?
N18 C19 C20 C25 -11.0(3) . . . . ?
C25 C20 C21 C22 -0.2(3) . . . . ?
C19 C20 C21 C22 178.75(19) . . . . ?
C20 C21 C22 C23 0.5(3) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 C25 -0.6(3) . . . . ?
C23 C24 C25 C20 0.9(3) . . . . ?
C21 C20 C25 C24 -0.5(3) . . . . ?
C19 C20 C25 C24 -179.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.037


####################################################################### 
# 
# 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_be34jea1n
_database_code_depnum_ccdc_archive 'CCDC 938292'
_audit_update_record             
;
2013-05-08 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;

_audit_creation_date             2013-05-06T18:55:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            DDJS-60
_chemical_formula_moiety         'C22 H17 N'
_chemical_formula_sum            'C22 H17 N'
_chemical_formula_weight         295.37
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.2713(12)
_cell_length_b                   14.110(4)
_cell_length_c                   25.725(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.832(5)
_cell_angle_gamma                90
_cell_volume                     1549.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3551
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      26.66
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8186
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_process_details   'BRUKER AXS - SADABS'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker X8 kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_number            19560
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             3570
_reflns_number_gt                2627
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APEX2 v2013.4-0 (Bruker AXS, 2013)'
_computing_cell_refinement       'APEX2 v2013.4-0 (Bruker AXS, 2013)'
_computing_data_reduction        'APEX2 v2013.4-0 (Bruker AXS, 2013)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0514P)²+0.6011P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3570
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.12
_refine_ls_wR_factor_gt          0.107
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.3477(3) 0.16475(10) 0.11571(5) 0.0146(3) Uani 1 1 d . . .
C2 C 0.5450(3) 0.24458(10) 0.12068(5) 0.0145(3) Uani 1 1 d . . .
C3 C 0.6279(3) 0.30256(10) 0.07753(5) 0.0171(3) Uani 1 1 d . . .
H3 H 0.5482 0.2874 0.0436 0.021 Uiso 1 1 calc R . .
C4 C 0.8192(4) 0.37912(10) 0.08432(6) 0.0207(3) Uani 1 1 d . . .
H4 H 0.8702 0.4165 0.0551 0.025 Uiso 1 1 calc R . .
C5 C 0.9436(4) 0.40399(11) 0.13426(6) 0.0209(3) Uani 1 1 d . . .
H5 H 1.0791 0.4571 0.1383 0.025 Uiso 1 1 calc R . .
C6 C 0.8683(3) 0.35170(10) 0.17628(6) 0.0190(3) Uani 1 1 d . . .
H6 H 0.9522 0.3687 0.2096 0.023 Uiso 1 1 calc R . .
C7 C 0.6654(3) 0.27158(10) 0.17138(5) 0.0162(3) Uani 1 1 d . . .
C8 C 0.5828(3) 0.21906(10) 0.21472(5) 0.0168(3) Uani 1 1 d . . .
H8 H 0.6629 0.2373 0.2481 0.02 Uiso 1 1 calc R . .
C9 C 0.3866(3) 0.14068(10) 0.21046(5) 0.0158(3) Uani 1 1 d . . .
C10 C 0.3052(3) 0.08669(11) 0.25495(5) 0.0187(3) Uani 1 1 d . . .
H10 H 0.3842 0.105 0.2884 0.022 Uiso 1 1 calc R . .
C11 C 0.1166(3) 0.00947(11) 0.25020(6) 0.0203(3) Uani 1 1 d . . .
H11 H 0.0646 -0.0256 0.2802 0.024 Uiso 1 1 calc R . .
C12 C -0.0031(3) -0.01889(11) 0.20047(6) 0.0197(3) Uani 1 1 d . . .
H12 H -0.1349 -0.073 0.1975 0.024 Uiso 1 1 calc R . .
C13 C 0.0691(3) 0.03060(10) 0.15709(5) 0.0168(3) Uani 1 1 d . . .
H13 H -0.0123 0.0102 0.1242 0.02 Uiso 1 1 calc R . .
C14 C 0.2650(3) 0.11274(10) 0.16008(5) 0.0144(3) Uani 1 1 d . . .
C15 C 0.2130(3) 0.13578(10) 0.06430(5) 0.0148(3) Uani 1 1 d . . .
H15 H -0.0068 0.1267 0.0604 0.018 Uiso 1 1 calc R . .
N16 N 0.3833(3) 0.12281(8) 0.02530(4) 0.0165(3) Uani 1 1 d . . .
C17 C 0.2201(3) 0.10080(10) -0.02446(5) 0.0171(3) Uani 1 1 d . . .
H17A H -0.0068 0.093 -0.019 0.021 Uiso 1 1 calc R . .
H17B H 0.3016 0.0408 -0.0387 0.021 Uiso 1 1 calc R . .
C18 C 0.2724(3) 0.18069(10) -0.06228(5) 0.0162(3) Uani 1 1 d . . .
C19 C 0.1498(4) 0.27008(11) -0.05212(6) 0.0219(3) Uani 1 1 d . . .
H19 H 0.0312 0.2797 -0.022 0.026 Uiso 1 1 calc R . .
C20 C 0.1994(4) 0.34492(12) -0.08553(6) 0.0277(4) Uani 1 1 d . . .
H20 H 0.1153 0.4056 -0.0782 0.033 Uiso 1 1 calc R . .
C21 C 0.3712(4) 0.33184(12) -0.12971(6) 0.0281(4) Uani 1 1 d . . .
H21 H 0.4058 0.3834 -0.1525 0.034 Uiso 1 1 calc R . .
C22 C 0.4922(4) 0.24336(13) -0.14041(6) 0.0277(4) Uani 1 1 d . . .
H22 H 0.6088 0.2339 -0.1708 0.033 Uiso 1 1 calc R . .
C23 C 0.4432(4) 0.16824(11) -0.10665(5) 0.0210(3) Uani 1 1 d . . .
H23 H 0.5279 0.1077 -0.1141 0.025 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.410(2) . ?
C1 C14 1.4113(19) . ?
C1 C15 1.4828(19) . ?
C2 C3 1.432(2) . ?
C2 C7 1.4381(19) . ?
C3 C4 1.362(2) . ?
C3 H3 0.95 . ?
C4 C5 1.419(2) . ?
C4 H4 0.95 . ?
C5 C6 1.356(2) . ?
C5 H5 0.95 . ?
C6 C7 1.427(2) . ?
C6 H6 0.95 . ?
C7 C8 1.393(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.95 . ?
C9 C10 1.427(2) . ?
C9 C14 1.4359(19) . ?
C10 C11 1.358(2) . ?
C10 H10 0.95 . ?
C11 C12 1.420(2) . ?
C11 H11 0.95 . ?
C12 C13 1.360(2) . ?
C12 H12 0.95 . ?
C13 C14 1.430(2) . ?
C13 H13 0.95 . ?
C15 N16 1.2709(18) . ?
C15 H15 0.95 . ?
N16 C17 1.4710(17) . ?
C17 C18 1.510(2) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C23 1.385(2) . ?
C18 C19 1.394(2) . ?
C19 C20 1.382(2) . ?
C19 H19 0.95 . ?
C20 C21 1.385(2) . ?
C20 H20 0.95 . ?
C21 C22 1.382(2) . ?
C21 H21 0.95 . ?
C22 C23 1.390(2) . ?
C22 H22 0.95 . ?
C23 H23 0.95 . ?

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 C14 120.42(12) . . ?
C2 C1 C15 120.98(12) . . ?
C14 C1 C15 118.56(13) . . ?
C1 C2 C3 123.21(13) . . ?
C1 C2 C7 119.29(13) . . ?
C3 C2 C7 117.48(13) . . ?
C4 C3 C2 121.04(13) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 121.20(14) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 119.73(14) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 121.29(13) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 121.27(13) . . ?
C8 C7 C2 119.49(13) . . ?
C6 C7 C2 119.24(13) . . ?
C9 C8 C7 121.85(13) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 121.55(13) . . ?
C8 C9 C14 119.30(13) . . ?
C10 C9 C14 119.15(13) . . ?
C11 C10 C9 121.00(13) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.17(14) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.67(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.30(13) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C1 C14 C13 122.63(12) . . ?
C1 C14 C9 119.64(13) . . ?
C13 C14 C9 117.71(12) . . ?
N16 C15 C1 121.89(13) . . ?
N16 C15 H15 119.1 . . ?
C1 C15 H15 119.1 . . ?
C15 N16 C17 116.75(12) . . ?
N16 C17 C18 109.11(12) . . ?
N16 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
N16 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C23 C18 C19 118.71(13) . . ?
C23 C18 C17 121.91(13) . . ?
C19 C18 C17 119.37(13) . . ?
C20 C19 C18 120.58(15) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 120.28(15) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.69(15) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 119.95(15) . . ?
C21 C22 H22 120 . . ?
C23 C22 H22 120 . . ?
C18 C23 C22 120.78(15) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?

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 C1 C2 C3 -177.48(13) . . . . ?
C15 C1 C2 C3 0.2(2) . . . . ?
C14 C1 C2 C7 1.0(2) . . . . ?
C15 C1 C2 C7 178.64(12) . . . . ?
C1 C2 C3 C4 179.90(14) . . . . ?
C7 C2 C3 C4 1.4(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C8 -178.64(14) . . . . ?
C5 C6 C7 C2 1.5(2) . . . . ?
C1 C2 C7 C8 -0.6(2) . . . . ?
C3 C2 C7 C8 177.96(13) . . . . ?
C1 C2 C7 C6 179.23(13) . . . . ?
C3 C2 C7 C6 -2.2(2) . . . . ?
C6 C7 C8 C9 -179.73(13) . . . . ?
C2 C7 C8 C9 0.1(2) . . . . ?
C7 C8 C9 C10 179.42(13) . . . . ?
C7 C8 C9 C14 0.0(2) . . . . ?
C8 C9 C10 C11 -179.10(14) . . . . ?
C14 C9 C10 C11 0.3(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C2 C1 C14 C13 -179.17(13) . . . . ?
C15 C1 C14 C13 3.1(2) . . . . ?
C2 C1 C14 C9 -0.9(2) . . . . ?
C15 C1 C14 C9 -178.58(12) . . . . ?
C12 C13 C14 C1 179.07(13) . . . . ?
C12 C13 C14 C9 0.7(2) . . . . ?
C8 C9 C14 C1 0.4(2) . . . . ?
C10 C9 C14 C1 -179.05(13) . . . . ?
C8 C9 C14 C13 178.73(13) . . . . ?
C10 C9 C14 C13 -0.67(19) . . . . ?
C2 C1 C15 N16 52.73(19) . . . . ?
C14 C1 C15 N16 -129.57(15) . . . . ?
C1 C15 N16 C17 -175.79(12) . . . . ?
C15 N16 C17 C18 114.78(14) . . . . ?
N16 C17 C18 C23 113.79(15) . . . . ?
N16 C17 C18 C19 -65.26(17) . . . . ?
C23 C18 C19 C20 -0.4(2) . . . . ?
C17 C18 C19 C20 178.71(14) . . . . ?
C18 C19 C20 C21 0.2(2) . . . . ?
C19 C20 C21 C22 0.3(2) . . . . ?
C20 C21 C22 C23 -0.5(2) . . . . ?
C19 C18 C23 C22 0.1(2) . . . . ?
C17 C18 C23 C22 -178.95(14) . . . . ?
C21 C22 C23 C18 0.3(2) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
