# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_AV_PKM_351
_database_code_depnum_ccdc_archive 'CCDC 1900529'
_audit_update_record             
;
2019-03-01 deposited with the CCDC.	2019-06-21 downloaded from the CCDC.
;

_audit_creation_date             2017-02-10T18:55:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C24  H18  N2'
_chemical_formula_sum            'C24 H18 N2'
_chemical_formula_weight         334.4

#----------------------------------------------------------------------------#
#                   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                   9.304(6)
_cell_length_b                   12.635(6)
_cell_length_c                   14.949(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.29(4)
_cell_angle_gamma                90
_cell_volume                     1734.2(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      2.122
_cell_measurement_theta_max      26.175
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704

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

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.0904
_diffrn_reflns_number            12137
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.122
_diffrn_reflns_theta_max         26.175
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_reflns_Friedel_coverage         0
_reflns_number_total             3397
_reflns_number_gt                1486
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0775P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.030(3)
_refine_ls_number_reflns         3397
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1475
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1657
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   0.89
_refine_ls_restrained_S_all      0.89
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 1.0032(2) 0.2774(2) 0.30585(14) 0.0597(7) Uani 1 1 d . . . . .
N1 N 0.5766(2) 0.4318(2) 0.34839(14) 0.0617(7) Uani 1 1 d . . . . .
C17 C 0.8029(3) 0.3445(2) 0.35243(16) 0.0522(7) Uani 1 1 d . . . . .
C18 C 0.8675(3) 0.4250(2) 0.30322(16) 0.0512(7) Uani 1 1 d . . . . .
C10 C 0.7306(3) 0.2146(3) 0.51099(17) 0.0529(8) Uani 1 1 d . . . . .
C9 C 0.6667(3) 0.3537(2) 0.39020(17) 0.0522(7) Uani 1 1 d . . . . .
C8 C 0.6285(3) 0.2912(2) 0.45906(16) 0.0527(8) Uani 1 1 d . . . . .
C7 C 0.4872(3) 0.3036(2) 0.48275(17) 0.0553(8) Uani 1 1 d . . . . .
C23 C 0.9925(3) 0.3811(3) 0.27621(16) 0.0526(7) Uani 1 1 d . . . . .
C2 C 0.3959(3) 0.3838(3) 0.43968(18) 0.0591(8) Uani 1 1 d . . . . .
C19 C 0.8354(3) 0.5306(3) 0.28048(16) 0.0579(8) Uani 1 1 d . . . . .
H19 H 0.753417 0.562942 0.296487 0.069 Uiso 1 1 calc R U . . .
C15 C 0.8376(3) 0.2512(3) 0.57889(17) 0.0605(8) Uani 1 1 d . . . . .
H15 H 0.844706 0.323229 0.591502 0.073 Uiso 1 1 calc R U . . .
C16 C 0.8903(3) 0.2569(3) 0.35112(17) 0.0620(8) Uani 1 1 d . . . . .
H16 H 0.874529 0.192246 0.377637 0.074 Uiso 1 1 calc R U . . .
C22 C 1.0851(3) 0.4374(3) 0.22944(17) 0.0607(8) Uani 1 1 d . . . . .
H22 H 1.167339 0.406031 0.212817 0.073 Uiso 1 1 calc R U . . .
C1 C 0.4503(3) 0.4449(2) 0.37464(18) 0.0638(9) Uani 1 1 d . . . . .
H1 H 0.391648 0.499574 0.347772 0.077 Uiso 1 1 calc R U . . .
C11 C 0.7224(3) 0.1067(3) 0.49607(19) 0.0657(9) Uani 1 1 d . . . . .
H11 H 0.648533 0.079827 0.452643 0.079 Uiso 1 1 calc R U . . .
C20 C 0.9275(3) 0.5862(3) 0.23382(18) 0.0654(9) Uani 1 1 d . . . . .
H20 H 0.90638 0.656519 0.218655 0.079 Uiso 1 1 calc R U . . .
C14 C 0.9338(3) 0.1819(3) 0.6280(2) 0.0681(9) Uani 1 1 d . . . . .
H14 H 1.004605 0.207692 0.673907 0.082 Uiso 1 1 calc R U . . .
C21 C 1.0505(3) 0.5404(3) 0.20891(18) 0.0673(9) Uani 1 1 d . . . . .
H21 H 1.110301 0.580448 0.177796 0.081 Uiso 1 1 calc R U . . .
C6 C 0.4331(3) 0.2400(3) 0.54795(18) 0.0688(9) Uani 1 1 d . . . . .
H6 H 0.491242 0.186583 0.57736 0.083 Uiso 1 1 calc R U . . .
C3 C 0.2555(3) 0.3992(3) 0.46310(19) 0.0694(9) Uani 1 1 d . . . . .
H3 H 0.196151 0.45318 0.435808 0.083 Uiso 1 1 calc R U . . .
C13 C 0.9267(3) 0.0764(3) 0.6104(2) 0.0711(9) Uani 1 1 d . . . . .
H13 H 0.99339 0.030458 0.643359 0.085 Uiso 1 1 calc R U . . .
C12 C 0.8212(4) 0.0379(3) 0.5441(2) 0.0735(9) Uani 1 1 d . . . . .
H12 H 0.815998 -0.034182 0.531462 0.088 Uiso 1 1 calc R U . . .
C4 C 0.2074(3) 0.3352(3) 0.5254(2) 0.0768(10) Uani 1 1 d . . . . .
H4 H 0.11434 0.344509 0.539314 0.092 Uiso 1 1 calc R U . . .
C5 C 0.2973(3) 0.2559(3) 0.56815(19) 0.0782(10) Uani 1 1 d . . . . .
H5 H 0.263988 0.213203 0.611171 0.094 Uiso 1 1 calc R U . . .
C24 C 1.1174(3) 0.2039(3) 0.2923(2) 0.0843(11) Uani 1 1 d . . . . .
H24A H 1.085362 0.13279 0.300162 0.126 Uiso 1 1 calc R U . . .
H24B H 1.203086 0.218145 0.335751 0.126 Uiso 1 1 calc R U . . .
H24C H 1.139483 0.212171 0.232175 0.126 Uiso 1 1 calc R U . . .



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

_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
N2 C16 1.363(3) . ?
N2 C23 1.382(3) . ?
N2 C24 1.450(3) . ?
N1 C1 1.308(3) . ?
N1 C9 1.377(3) . ?
C17 C16 1.375(4) . ?
C17 C18 1.442(4) . ?
C17 C9 1.473(4) . ?
C18 C19 1.397(4) . ?
C18 C23 1.405(4) . ?
C10 C11 1.381(4) . ?
C10 C15 1.382(3) . ?
C10 C8 1.485(4) . ?
C9 C8 1.389(4) . ?
C8 C7 1.424(3) . ?
C7 C2 1.409(4) . ?
C7 C6 1.417(4) . ?
C23 C22 1.390(4) . ?
C2 C1 1.399(4) . ?
C2 C3 1.419(4) . ?
C19 C20 1.381(4) . ?
C19 H19 0.93 . ?
C15 C14 1.376(4) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
C22 C21 1.364(4) . ?
C22 H22 0.93 . ?
C1 H1 0.93 . ?
C11 C12 1.379(4) . ?
C11 H11 0.93 . ?
C20 C21 1.386(4) . ?
C20 H20 0.93 . ?
C14 C13 1.359(4) . ?
C14 H14 0.93 . ?
C21 H21 0.93 . ?
C6 C5 1.360(4) . ?
C6 H6 0.93 . ?
C3 C4 1.362(4) . ?
C3 H3 0.93 . ?
C13 C12 1.367(4) . ?
C13 H13 0.93 . ?
C12 H12 0.93 . ?
C4 C5 1.393(4) . ?
C4 H4 0.93 . ?
C5 H5 0.93 . ?
C24 H24A 0.96 . ?
C24 H24B 0.96 . ?
C24 H24C 0.96 . ?

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
C16 N2 C23 108.5(2) . . ?
C16 N2 C24 126.0(3) . . ?
C23 N2 C24 125.4(2) . . ?
C1 N1 C9 117.7(2) . . ?
C16 C17 C18 105.3(2) . . ?
C16 C17 C9 128.1(3) . . ?
C18 C17 C9 126.5(3) . . ?
C19 C18 C23 117.5(3) . . ?
C19 C18 C17 135.1(3) . . ?
C23 C18 C17 107.5(3) . . ?
C11 C10 C15 117.6(3) . . ?
C11 C10 C8 123.0(3) . . ?
C15 C10 C8 119.4(3) . . ?
N1 C9 C8 122.2(2) . . ?
N1 C9 C17 112.4(2) . . ?
C8 C9 C17 125.3(3) . . ?
C9 C8 C7 118.6(3) . . ?
C9 C8 C10 122.7(2) . . ?
C7 C8 C10 118.7(2) . . ?
C2 C7 C6 117.8(2) . . ?
C2 C7 C8 118.6(2) . . ?
C6 C7 C8 123.6(3) . . ?
N2 C23 C22 128.9(3) . . ?
N2 C23 C18 107.6(2) . . ?
C22 C23 C18 123.5(3) . . ?
C1 C2 C7 117.1(3) . . ?
C1 C2 C3 123.1(3) . . ?
C7 C2 C3 119.8(3) . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C14 C15 C10 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
N2 C16 C17 111.0(3) . . ?
N2 C16 H16 124.5 . . ?
C17 C16 H16 124.5 . . ?
C21 C22 C23 117.3(3) . . ?
C21 C22 H22 121.4 . . ?
C23 C22 H22 121.4 . . ?
N1 C1 C2 125.6(3) . . ?
N1 C1 H1 117.2 . . ?
C2 C1 H1 117.2 . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C19 C20 C21 122.0(3) . . ?
C19 C20 H20 119 . . ?
C21 C20 H20 119 . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

####################################################################### 
# 
# 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_AV_PKM_353
_database_code_depnum_ccdc_archive 'CCDC 1900530'
_audit_update_record             
;
2019-03-01 deposited with the CCDC.	2019-06-21 downloaded from the CCDC.
;

_audit_creation_date             2017-02-10T18:56:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C25  H17  N1'
_chemical_formula_sum            'C25 H17 N'
_chemical_formula_weight         331.39

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5750(2)
_cell_length_b                   9.8132(2)
_cell_length_c                   11.2552(2)
_cell_angle_alpha                102.2380(10)
_cell_angle_beta                 93.9930(10)
_cell_angle_gamma                110.8450(10)
_cell_volume                     854.02(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      1.875
_cell_measurement_theta_max      25.091
_cell_measurement_wavelength     0.71073

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


_exptl_crystal_description       block
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348

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

_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_number            13786
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.875
_diffrn_reflns_theta_max         25.091
_diffrn_reflns_theta_full        25.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             3042
_reflns_number_gt                2509
_reflns_threshold_expression     'I > 2σ(I)'

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


_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.4726P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3042
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   0.712
_refine_ls_restrained_S_all      0.712
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.47252(14) 0.12839(13) 0.91774(10) 0.0266(3) Uani 1 1 d . . . . .
C6 C -0.09561(19) 0.12786(17) 1.26929(13) 0.0355(4) Uani 1 1 d . . . . .
H6 H -0.169595 0.117753 1.326417 0.043 Uiso 1 1 calc R U . . .
C7 C -0.10575(19) 0.20521(16) 1.18314(13) 0.0328(4) Uani 1 1 d . . . . .
H7 H -0.187837 0.246536 1.181471 0.039 Uiso 1 1 calc R U . . .
C8 C 0.00683(17) 0.22301(15) 1.09680(12) 0.0269(3) Uani 1 1 d . . . . .
C3 C 0.13117(17) 0.15920(14) 1.09891(12) 0.0249(3) Uani 1 1 d . . . . .
C2 C 0.24460(16) 0.17846(14) 1.00857(12) 0.0235(3) Uani 1 1 d . . . . .
C1 C 0.36481(17) 0.11113(15) 0.99716(12) 0.0254(3) Uani 1 1 d . . . . .
H1 H 0.368736 0.050073 1.049279 0.03 Uiso 1 1 calc R U . . .
C13 C 0.46863(17) 0.21870(15) 0.84170(12) 0.0240(3) Uani 1 1 d . . . . .
C14 C 0.59737(17) 0.23516(16) 0.75795(12) 0.0253(3) Uani 1 1 d . . . . .
C19 C 0.60292(18) 0.10701(17) 0.67923(13) 0.0314(3) Uani 1 1 d . . . . .
H19 H 0.525038 0.012289 0.67862 0.038 Uiso 1 1 calc R U . . .
C18 C 0.72313(19) 0.11949(18) 0.60208(14) 0.0367(4) Uani 1 1 d . . . . .
H18 H 0.72395 0.033393 0.548659 0.044 Uiso 1 1 calc R U . . .
C17 C 0.84213(18) 0.25922(19) 0.60390(13) 0.0356(4) Uani 1 1 d . . . . .
H17 H 0.923957 0.267208 0.552839 0.043 Uiso 1 1 calc R U . . .
C11 C 0.23576(16) 0.26615(14) 0.92538(12) 0.0227(3) Uani 1 1 d . . . . .
C12 C 0.35289(16) 0.28785(14) 0.84142(12) 0.0228(3) Uani 1 1 d . . . . .
C16 C 0.83861(18) 0.38718(18) 0.68227(13) 0.0326(3) Uani 1 1 d . . . . .
H16 H 0.918816 0.481398 0.684269 0.039 Uiso 1 1 calc R U . . .
C15 C 0.71608(17) 0.37534(16) 0.75770(12) 0.0278(3) Uani 1 1 d . . . . .
H15 H 0.713131 0.462056 0.808738 0.033 Uiso 1 1 calc R U . . .
C20 C 0.34963(16) 0.38189(15) 0.75367(12) 0.0232(3) Uani 1 1 d . . . . .
C21 C 0.40166(17) 0.53715(15) 0.79683(13) 0.0271(3) Uani 1 1 d . . . . .
H21 H 0.434311 0.581775 0.880858 0.032 Uiso 1 1 calc R U . . .
C22 C 0.40532(18) 0.62611(17) 0.71565(14) 0.0320(3) Uani 1 1 d . . . . .
H22 H 0.443095 0.730241 0.745148 0.038 Uiso 1 1 calc R U . . .
C23 C 0.35306(18) 0.56056(19) 0.59123(14) 0.0358(4) Uani 1 1 d . . . . .
H23 H 0.354945 0.620302 0.536875 0.043 Uiso 1 1 calc R U . . .
C24 C 0.29790(18) 0.40600(19) 0.54751(13) 0.0358(4) Uani 1 1 d . . . . .
H24 H 0.261405 0.361587 0.463721 0.043 Uiso 1 1 calc R U . . .
C25 C 0.29680(17) 0.31716(17) 0.62794(12) 0.0290(3) Uani 1 1 d . . . . .
H25 H 0.260445 0.213228 0.597779 0.035 Uiso 1 1 calc R U . . .
C10 C 0.10496(17) 0.32564(15) 0.92528(12) 0.0256(3) Uani 1 1 d . . . . .
H10 H 0.095807 0.380304 0.868845 0.031 Uiso 1 1 calc R U . . .
C9 C -0.00459(17) 0.30304(15) 1.00614(13) 0.0282(3) Uani 1 1 d . . . . .
H9 H -0.089925 0.34047 1.002942 0.034 Uiso 1 1 calc R U . . .
C4 C 0.13736(18) 0.07899(16) 1.18788(12) 0.0292(3) Uani 1 1 d . . . . .
H4 H 0.217503 0.035604 1.190308 0.035 Uiso 1 1 calc R U . . .
C5 C 0.02645(19) 0.06401(17) 1.27118(13) 0.0345(4) Uani 1 1 d . . . . .
H5 H 0.032583 0.010847 1.329456 0.041 Uiso 1 1 calc R U . . .



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

_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 C1 1.3224(17) . ?
N1 C13 1.3629(17) . ?
C6 C7 1.368(2) . ?
C6 C5 1.399(2) . ?
C6 H6 0.93 . ?
C7 C8 1.4105(19) . ?
C7 H7 0.93 . ?
C8 C3 1.4168(19) . ?
C8 C9 1.431(2) . ?
C3 C4 1.4077(19) . ?
C3 C2 1.4505(18) . ?
C2 C1 1.4080(19) . ?
C2 C11 1.4146(19) . ?
C1 H1 0.93 . ?
C13 C12 1.3875(18) . ?
C13 C14 1.4886(18) . ?
C14 C15 1.391(2) . ?
C14 C19 1.3946(19) . ?
C19 C18 1.383(2) . ?
C19 H19 0.93 . ?
C18 C17 1.382(2) . ?
C18 H18 0.93 . ?
C17 C16 1.384(2) . ?
C17 H17 0.93 . ?
C11 C12 1.4186(18) . ?
C11 C10 1.4370(18) . ?
C12 C20 1.4930(18) . ?
C16 C15 1.3847(19) . ?
C16 H16 0.93 . ?
C15 H15 0.93 . ?
C20 C21 1.3888(19) . ?
C20 C25 1.3914(19) . ?
C21 C22 1.3859(19) . ?
C21 H21 0.93 . ?
C22 C23 1.379(2) . ?
C22 H22 0.93 . ?
C23 C24 1.381(2) . ?
C23 H23 0.93 . ?
C24 C25 1.382(2) . ?
C24 H24 0.93 . ?
C25 H25 0.93 . ?
C10 C9 1.3476(19) . ?
C10 H10 0.93 . ?
C9 H9 0.93 . ?
C4 C5 1.3742(19) . ?
C4 H4 0.93 . ?
C5 H5 0.93 . ?

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
C1 N1 C13 118.02(11) . . ?
C7 C6 C5 119.79(13) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.77(14) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C3 119.58(13) . . ?
C7 C8 C9 120.75(13) . . ?
C3 C8 C9 119.67(12) . . ?
C4 C3 C8 118.32(12) . . ?
C4 C3 C2 123.27(12) . . ?
C8 C3 C2 118.41(12) . . ?
C1 C2 C11 116.89(12) . . ?
C1 C2 C3 122.99(12) . . ?
C11 C2 C3 120.10(12) . . ?
N1 C1 C2 124.77(13) . . ?
N1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
N1 C13 C12 122.74(12) . . ?
N1 C13 C14 114.36(11) . . ?
C12 C13 C14 122.90(12) . . ?
C15 C14 C19 118.53(12) . . ?
C15 C14 C13 121.83(12) . . ?
C19 C14 C13 119.62(12) . . ?
C18 C19 C14 120.60(14) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C19 C18 C17 120.38(13) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C17 C16 119.53(13) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C2 C11 C12 118.75(12) . . ?
C2 C11 C10 119.16(12) . . ?
C12 C11 C10 122.04(12) . . ?
C13 C12 C11 118.72(12) . . ?
C13 C12 C20 120.91(11) . . ?
C11 C12 C20 120.37(11) . . ?
C17 C16 C15 120.22(14) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C15 C14 120.71(13) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C21 C20 C25 118.74(13) . . ?
C21 C20 C12 120.04(12) . . ?
C25 C20 C12 121.21(12) . . ?
C22 C21 C20 120.51(13) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 120.14(14) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.85(14) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 120.17(14) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C20 120.56(14) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?
C9 C10 C11 120.68(13) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C9 C8 121.79(12) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C5 C4 C3 120.82(13) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.72(14) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 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
C5 C6 C7 C8 -0.7(2) . . . . ?
C6 C7 C8 C3 0.4(2) . . . . ?
C6 C7 C8 C9 179.57(13) . . . . ?
C7 C8 C3 C4 0.23(19) . . . . ?
C9 C8 C3 C4 -178.95(12) . . . . ?
C7 C8 C3 C2 179.63(12) . . . . ?
C9 C8 C3 C2 0.45(19) . . . . ?
C4 C3 C2 C1 3.8(2) . . . . ?
C8 C3 C2 C1 -175.54(12) . . . . ?
C4 C3 C2 C11 -177.23(12) . . . . ?
C8 C3 C2 C11 3.41(19) . . . . ?
C13 N1 C1 C2 0.5(2) . . . . ?
C11 C2 C1 N1 2.4(2) . . . . ?
C3 C2 C1 N1 -178.60(12) . . . . ?
C1 N1 C13 C12 -2.5(2) . . . . ?
C1 N1 C13 C14 178.32(11) . . . . ?
N1 C13 C14 C15 -122.18(14) . . . . ?
C12 C13 C14 C15 58.60(19) . . . . ?
N1 C13 C14 C19 56.26(17) . . . . ?
C12 C13 C14 C19 -122.97(15) . . . . ?
C15 C14 C19 C18 -0.5(2) . . . . ?
C13 C14 C19 C18 -178.97(13) . . . . ?
C14 C19 C18 C17 1.5(2) . . . . ?
C19 C18 C17 C16 -1.0(2) . . . . ?
C1 C2 C11 C12 -3.49(18) . . . . ?
C3 C2 C11 C12 177.50(11) . . . . ?
C1 C2 C11 C10 174.21(12) . . . . ?
C3 C2 C11 C10 -4.80(19) . . . . ?
N1 C13 C12 C11 1.3(2) . . . . ?
C14 C13 C12 C11 -179.58(11) . . . . ?
N1 C13 C12 C20 -178.00(12) . . . . ?
C14 C13 C12 C20 1.2(2) . . . . ?
C2 C11 C12 C13 1.81(19) . . . . ?
C10 C11 C12 C13 -175.82(12) . . . . ?
C2 C11 C12 C20 -178.92(11) . . . . ?
C10 C11 C12 C20 3.45(19) . . . . ?
C18 C17 C16 C15 -0.4(2) . . . . ?
C17 C16 C15 C14 1.4(2) . . . . ?
C19 C14 C15 C16 -1.0(2) . . . . ?
C13 C14 C15 C16 177.50(12) . . . . ?
C13 C12 C20 C21 -109.98(15) . . . . ?
C11 C12 C20 C21 70.77(17) . . . . ?
C13 C12 C20 C25 69.30(17) . . . . ?
C11 C12 C20 C25 -109.95(14) . . . . ?
C25 C20 C21 C22 -1.80(19) . . . . ?
C12 C20 C21 C22 177.50(12) . . . . ?
C20 C21 C22 C23 1.7(2) . . . . ?
C21 C22 C23 C24 -0.4(2) . . . . ?
C22 C23 C24 C25 -0.7(2) . . . . ?
C23 C24 C25 C20 0.6(2) . . . . ?
C21 C20 C25 C24 0.69(19) . . . . ?
C12 C20 C25 C24 -178.60(12) . . . . ?
C2 C11 C10 C9 2.3(2) . . . . ?
C12 C11 C10 C9 179.94(12) . . . . ?
C11 C10 C9 C8 1.6(2) . . . . ?
C7 C8 C9 C10 177.83(13) . . . . ?
C3 C8 C9 C10 -3.0(2) . . . . ?
C8 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 C5 -179.87(12) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C7 C6 C5 C4 0.5(2) . . . . ?

