# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_sgcnitrile
_database_code_depnum_ccdc_archive 'CCDC 1063744'
_audit_update_record             
;
2015-05-07 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H14 N2'
_chemical_formula_sum            'C22 H14 N2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         306.35

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8666(5)
_cell_length_b                   11.4535(10)
_cell_length_c                   12.2113(12)
_cell_angle_alpha                83.981(8)
_cell_angle_beta                 81.526(8)
_cell_angle_gamma                76.578(8)
_cell_volume                     787.26(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1393
_cell_measurement_theta_min      3.5870
_cell_measurement_theta_max      28.7440
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99412
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6123
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         29.16
_reflns_number_total             3630
_reflns_number_gt                2541
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0485P)²+0.1069P] 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         3630
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.7683(3) 1.00540(14) 0.90902(12) 0.0274(4) Uani 1 1 d . . .
N2 N 1.9672(3) 0.36880(15) 0.90783(14) 0.0357(4) Uani 1 1 d . . .
C1 C 0.6349(3) 1.02861(15) 0.82284(14) 0.0216(4) Uani 1 1 d . . .
C2 C 0.4276(3) 1.12179(16) 0.83235(15) 0.0278(4) Uani 1 1 d . . .
H2A H 0.3918 1.1690 0.8947 0.033 Uiso 1 1 calc R . .
C3 C 0.2793(3) 1.14414(17) 0.75272(15) 0.0288(4) Uani 1 1 d . . .
H3A H 0.1387 1.2052 0.7607 0.035 Uiso 1 1 calc R . .
C4 C 0.3348(3) 1.07649(16) 0.65853(15) 0.0253(4) Uani 1 1 d . . .
H4A H 0.2311 1.0923 0.6033 0.030 Uiso 1 1 calc R . .
C5 C 0.5367(3) 0.98827(15) 0.64613(14) 0.0227(4) Uani 1 1 d . . .
H5A H 0.5740 0.9455 0.5809 0.027 Uiso 1 1 calc R . .
C6 C 0.6917(3) 0.95928(15) 0.72875(14) 0.0195(4) Uani 1 1 d . . .
C7 C 0.8958(3) 0.86229(15) 0.72330(14) 0.0191(4) Uani 1 1 d . . .
C8 C 1.0267(3) 0.83816(15) 0.81200(14) 0.0203(4) Uani 1 1 d . . .
C9 C 0.9522(3) 0.91412(16) 0.90190(15) 0.0255(4) Uani 1 1 d . . .
H9A H 1.0436 0.8973 0.9621 0.031 Uiso 1 1 calc R . .
C10 C 0.9588(3) 0.79096(14) 0.62273(14) 0.0194(4) Uani 1 1 d . . .
C11 C 0.8149(3) 0.71731(15) 0.60010(15) 0.0227(4) Uani 1 1 d . . .
H11A H 0.6754 0.7118 0.6490 0.027 Uiso 1 1 calc R . .
C12 C 0.8748(3) 0.65209(15) 0.50639(15) 0.0262(4) Uani 1 1 d . . .
H12A H 0.7770 0.6014 0.4920 0.031 Uiso 1 1 calc R . .
C13 C 1.0766(3) 0.66044(16) 0.43360(15) 0.0296(4) Uani 1 1 d . . .
H13A H 1.1175 0.6153 0.3698 0.036 Uiso 1 1 calc R . .
C14 C 1.2177(3) 0.73468(17) 0.45440(16) 0.0297(4) Uani 1 1 d . . .
H14A H 1.3549 0.7415 0.4043 0.036 Uiso 1 1 calc R . .
C15 C 1.1596(3) 0.79954(16) 0.54852(15) 0.0250(4) Uani 1 1 d . . .
H15A H 1.2579 0.8502 0.5623 0.030 Uiso 1 1 calc R . .
C16 C 1.2355(3) 0.73684(15) 0.82474(14) 0.0204(4) Uani 1 1 d . . .
C17 C 1.2483(3) 0.62129(16) 0.79140(15) 0.0233(4) Uani 1 1 d . . .
H17A H 1.1268 0.6083 0.7537 0.028 Uiso 1 1 calc R . .
C18 C 1.4343(3) 0.52641(16) 0.81244(14) 0.0244(4) Uani 1 1 d . . .
H18A H 1.4397 0.4490 0.7895 0.029 Uiso 1 1 calc R . .
C19 C 1.6138(3) 0.54445(16) 0.86725(14) 0.0232(4) Uani 1 1 d . . .
C20 C 1.6055(3) 0.65809(16) 0.90120(14) 0.0233(4) Uani 1 1 d . . .
H20A H 1.7276 0.6705 0.9388 0.028 Uiso 1 1 calc R . .
C21 C 1.4185(3) 0.75276(16) 0.87990(14) 0.0220(4) Uani 1 1 d . . .
H21A H 1.4141 0.8300 0.9031 0.026 Uiso 1 1 calc R . .
C22 C 1.8100(3) 0.44593(17) 0.88995(15) 0.0257(4) Uani 1 1 d . . .


_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 1.316(2) . ?
N1 C1 1.371(2) . ?
N2 C22 1.149(2) . ?
C1 C2 1.419(2) . ?
C1 C6 1.420(2) . ?
C2 C3 1.365(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.410(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.368(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.419(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.431(2) . ?
C7 C8 1.387(2) . ?
C7 C10 1.500(2) . ?
C8 C9 1.427(2) . ?
C8 C16 1.494(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.396(2) . ?
C10 C15 1.393(2) . ?
C11 C12 1.389(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.388(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.381(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.391(3) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C17 1.407(2) . ?
C16 C21 1.403(2) . ?
C17 C18 1.383(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.391(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.395(2) . ?
C19 C22 1.449(2) . ?
C20 C21 1.385(2) . ?
C20 H20A 0.9500 . ?
C21 H21A 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
C9 N1 C1 117.00(15) . . ?
N1 C1 C2 117.74(16) . . ?
N1 C1 C6 122.23(15) . . ?
C2 C1 C6 119.96(15) . . ?
C3 C2 C1 120.56(17) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 119.98(17) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 120.52(16) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 121.33(16) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C7 123.39(15) . . ?
C5 C6 C1 117.60(16) . . ?
C7 C6 C1 118.98(15) . . ?
C8 C7 C6 118.25(15) . . ?
C8 C7 C10 122.83(15) . . ?
C6 C7 C10 118.93(14) . . ?
C7 C8 C9 117.64(16) . . ?
C7 C8 C16 126.14(16) . . ?
C9 C8 C16 116.18(15) . . ?
N1 C9 C8 125.88(16) . . ?
N1 C9 H9A 117.1 . . ?
C8 C9 H9A 117.1 . . ?
C11 C10 C15 118.74(16) . . ?
C11 C10 C7 120.88(15) . . ?
C15 C10 C7 120.35(15) . . ?
C10 C11 C12 120.28(17) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C13 C12 C11 120.46(17) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C12 C13 C14 119.61(17) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C13 C14 C15 120.21(18) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C10 C15 C14 120.69(16) . . ?
C10 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C17 C16 C21 117.77(16) . . ?
C17 C16 C8 122.31(15) . . ?
C21 C16 C8 119.71(15) . . ?
C18 C17 C16 121.23(16) . . ?
C18 C17 H17A 119.4 . . ?
C16 C17 H17A 119.4 . . ?
C17 C18 C19 119.93(16) . . ?
C17 C18 H18A 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C20 C19 C18 120.01(16) . . ?
C20 C19 C22 119.37(16) . . ?
C18 C19 C22 120.62(16) . . ?
C21 C20 C19 119.77(16) . . ?
C21 C20 H20A 120.1 . . ?
C19 C20 H20A 120.1 . . ?
C20 C21 C16 121.29(16) . . ?
C20 C21 H21A 119.4 . . ?
C16 C21 H21A 119.4 . . ?
N2 C22 C19 179.20(19) . . ?

_diffrn_measured_fraction_theta_max 0.855
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_rp8123
_database_code_depnum_ccdc_archive 'CCDC 1063745'
_audit_update_record             
;
2015-05-07 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H15 N O2'
_chemical_formula_sum            'C22 H15 N O2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            orange

_diffrn_ambient_temperature      152(2)
_chemical_formula_weight         325.35

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   10.0557(10)
_cell_length_b                   10.3647(11)
_cell_length_c                   15.6302(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.658(4)
_cell_angle_gamma                90.00
_cell_volume                     1614.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    152(2)
_cell_measurement_reflns_used    9929
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      26.27
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9664
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41068
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         26.38
_reflns_number_total             3299
_reflns_number_gt                2665
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_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)+(0.0518P)²+0.6768P] 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         3299
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.14383(11) 0.82330(10) 0.87514(7) 0.0367(3) Uani 1 1 d . . .
O2 O 0.03150(10) 1.01091(10) 0.87934(7) 0.0287(3) Uani 1 1 d . . .
N N 0.34729(12) 1.18203(11) 1.02537(8) 0.0263(3) Uani 1 1 d . . .
C1 C 0.25571(15) 1.12069(14) 0.97293(9) 0.0252(3) Uani 1 1 d . . .
H1A H 0.2035 1.1697 0.9293 0.030 Uiso 1 1 calc R . .
C2 C 0.42062(14) 1.11071(14) 1.08908(9) 0.0229(3) Uani 1 1 d . . .
C3 C 0.52034(15) 1.17503(14) 1.14583(9) 0.0267(3) Uani 1 1 d . . .
H3A H 0.5362 1.2643 1.1377 0.032 Uiso 1 1 calc R . .
C4 C 0.59406(15) 1.11069(15) 1.21210(10) 0.0294(3) Uani 1 1 d . . .
H4A H 0.6615 1.1548 1.2493 0.035 Uiso 1 1 calc R . .
C5 C 0.57004(16) 0.97903(15) 1.22529(10) 0.0305(3) Uani 1 1 d . . .
H5A H 0.6199 0.9352 1.2724 0.037 Uiso 1 1 calc R . .
C6 C 0.47562(15) 0.91324(14) 1.17100(9) 0.0265(3) Uani 1 1 d . . .
H6A H 0.4610 0.8242 1.1808 0.032 Uiso 1 1 calc R . .
C7 C 0.39918(14) 0.97629(13) 1.10023(9) 0.0215(3) Uani 1 1 d . . .
C8 C 0.30027(13) 0.91200(13) 1.04090(9) 0.0207(3) Uani 1 1 d . . .
C9 C 0.22902(14) 0.98620(13) 0.97668(9) 0.0222(3) Uani 1 1 d . . .
C10 C 0.13296(14) 0.92737(13) 0.90636(9) 0.0236(3) Uani 1 1 d . . .
C11 C -0.06501(14) 0.97492(14) 0.80900(9) 0.0244(3) Uani 1 1 d . . .
C12 C -0.13297(15) 0.85917(15) 0.80814(10) 0.0304(3) Uani 1 1 d . . .
H12A H -0.1142 0.7992 0.8541 0.037 Uiso 1 1 calc R . .
C13 C -0.22957(16) 0.83270(17) 0.73820(11) 0.0365(4) Uani 1 1 d . . .
H13A H -0.2768 0.7531 0.7359 0.044 Uiso 1 1 calc R . .
C14 C -0.25782(16) 0.92077(16) 0.67189(11) 0.0350(4) Uani 1 1 d . . .
H14A H -0.3233 0.9012 0.6240 0.042 Uiso 1 1 calc R . .
C15 C -0.19088(16) 1.03712(16) 0.67528(11) 0.0338(4) Uani 1 1 d . . .
H15A H -0.2118 1.0985 0.6303 0.041 Uiso 1 1 calc R . .
C16 C -0.09283(15) 1.06498(14) 0.74430(10) 0.0291(3) Uani 1 1 d . . .
H16A H -0.0459 1.1447 0.7468 0.035 Uiso 1 1 calc R . .
C17 C 0.27166(14) 0.77140(13) 1.05075(9) 0.0220(3) Uani 1 1 d . . .
C18 C 0.36995(15) 0.67809(13) 1.04467(9) 0.0233(3) Uani 1 1 d . . .
H18A H 0.4576 0.7034 1.0352 0.028 Uiso 1 1 calc R . .
C19 C 0.33966(16) 0.54793(14) 1.05251(9) 0.0272(3) Uani 1 1 d . . .
H19A H 0.4066 0.4847 1.0475 0.033 Uiso 1 1 calc R . .
C20 C 0.21314(17) 0.50975(15) 1.06752(10) 0.0319(4) Uani 1 1 d . . .
H20A H 0.1930 0.4207 1.0725 0.038 Uiso 1 1 calc R . .
C21 C 0.11595(16) 0.60196(16) 1.07526(11) 0.0342(4) Uani 1 1 d . . .
H21A H 0.0293 0.5763 1.0866 0.041 Uiso 1 1 calc R . .
C22 C 0.14467(15) 0.73202(15) 1.06646(10) 0.0285(3) Uani 1 1 d . . .
H22A H 0.0771 0.7947 1.0712 0.034 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
O1 C10 1.1949(18) . ?
O2 C10 1.3616(17) . ?
O2 C11 1.4162(17) . ?
N C1 1.3126(19) . ?
N C2 1.3733(18) . ?
C1 C9 1.422(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.414(2) . ?
C2 C7 1.424(2) . ?
C3 C4 1.365(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.406(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.368(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.419(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.4308(19) . ?
C8 C9 1.3859(19) . ?
C8 C17 1.4974(19) . ?
C9 C10 1.4932(19) . ?
C11 C16 1.377(2) . ?
C11 C12 1.380(2) . ?
C12 C13 1.390(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.379(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C22 1.393(2) . ?
C17 C18 1.395(2) . ?
C18 C19 1.392(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.382(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.384(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.389(2) . ?
C21 H21A 0.9500 . ?
C22 H22A 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
C10 O2 C11 118.75(11) . . ?
C1 N C2 117.15(12) . . ?
N C1 C9 124.72(13) . . ?
N C1 H1A 117.6 . . ?
C9 C1 H1A 117.6 . . ?
N C2 C3 117.94(13) . . ?
N C2 C7 122.67(13) . . ?
C3 C2 C7 119.39(13) . . ?
C4 C3 C2 120.92(14) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 119.94(14) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 120.76(14) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C5 C6 C7 120.86(14) . . ?
C5 C6 H6A 119.6 . . ?
C7 C6 H6A 119.6 . . ?
C2 C7 C6 118.08(13) . . ?
C2 C7 C8 118.67(12) . . ?
C6 C7 C8 123.24(13) . . ?
C9 C8 C7 117.30(12) . . ?
C9 C8 C17 121.78(12) . . ?
C7 C8 C17 120.87(12) . . ?
C8 C9 C1 119.43(13) . . ?
C8 C9 C10 121.86(12) . . ?
C1 C9 C10 118.49(12) . . ?
O1 C10 O2 123.56(13) . . ?
O1 C10 C9 125.72(13) . . ?
O2 C10 C9 110.68(12) . . ?
C16 C11 C12 122.02(14) . . ?
C16 C11 O2 116.27(13) . . ?
C12 C11 O2 121.59(13) . . ?
C11 C12 C13 118.21(15) . . ?
C11 C12 H12A 120.9 . . ?
C13 C12 H12A 120.9 . . ?
C14 C13 C12 120.79(15) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C13 C14 C15 119.90(15) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 C16 120.22(15) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C11 C16 C15 118.83(14) . . ?
C11 C16 H16A 120.6 . . ?
C15 C16 H16A 120.6 . . ?
C22 C17 C18 118.90(13) . . ?
C22 C17 C8 119.77(13) . . ?
C18 C17 C8 121.33(13) . . ?
C17 C18 C19 120.03(14) . . ?
C17 C18 H18A 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C20 C19 C18 120.64(14) . . ?
C20 C19 H19A 119.7 . . ?
C18 C19 H19A 119.7 . . ?
C19 C20 C21 119.60(14) . . ?
C19 C20 H20A 120.2 . . ?
C21 C20 H20A 120.2 . . ?
C22 C21 C20 120.19(15) . . ?
C22 C21 H21A 119.9 . . ?
C20 C21 H21A 119.9 . . ?
C17 C22 C21 120.62(14) . . ?
C17 C22 H22A 119.7 . . ?
C21 C22 H22A 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_rp9162
_database_code_depnum_ccdc_archive 'CCDC 1063746'
_audit_update_record             
;
2015-05-07 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H10 N2'
_chemical_formula_sum            'C16 H10 N2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         230.26

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/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   11.4760(11)
_cell_length_b                   6.7685(5)
_cell_length_c                   15.8831(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.572(10)
_cell_angle_gamma                90.00
_cell_volume                     1182.48(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    952
_cell_measurement_theta_min      3.2840
_cell_measurement_theta_max      28.9680
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5267
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         29.22
_reflns_number_total             2774
_reflns_number_gt                1598
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0606P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2774
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1158
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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 0.33179(13) 0.17539(18) 0.30142(11) 0.0444(4) Uani 1 1 d . . .
N2 N -0.00196(15) 0.2016(3) 0.42297(12) 0.0629(5) Uani 1 1 d . . .
C1 C 0.28201(16) 0.1769(2) 0.21247(13) 0.0396(4) Uani 1 1 d . . .
C2 C 0.36101(18) 0.1716(2) 0.15887(16) 0.0516(5) Uani 1 1 d . . .
H2A H 0.4446 0.1692 0.1848 0.062 Uiso 1 1 calc R . .
C3 C 0.3171(2) 0.1699(3) 0.07035(17) 0.0601(6) Uani 1 1 d . . .
H3A H 0.3706 0.1681 0.0361 0.072 Uiso 1 1 calc R . .
C4 C 0.1914(2) 0.1707(3) 0.02993(14) 0.0597(6) Uani 1 1 d . . .
H4A H 0.1621 0.1672 -0.0310 0.072 Uiso 1 1 calc R . .
C5 C 0.11183(18) 0.1767(2) 0.07914(13) 0.0490(5) Uani 1 1 d . . .
H5A H 0.0287 0.1776 0.0514 0.059 Uiso 1 1 calc R . .
C6 C 0.15417(15) 0.1815(2) 0.17184(12) 0.0361(4) Uani 1 1 d . . .
C7 C 0.07586(15) 0.1868(2) 0.22664(11) 0.0342(4) Uani 1 1 d . . .
C8 C 0.12890(15) 0.1817(2) 0.31580(12) 0.0358(4) Uani 1 1 d . . .
C9 C 0.25718(16) 0.1765(2) 0.35001(13) 0.0423(4) Uani 1 1 d . . .
H9A H 0.2902 0.1737 0.4107 0.051 Uiso 1 1 calc R . .
C10 C -0.05838(15) 0.1973(2) 0.18946(11) 0.0386(4) Uani 1 1 d . . .
C11 C -0.11272(18) 0.3608(3) 0.14198(13) 0.0520(5) Uani 1 1 d . . .
H11A H -0.0651 0.4649 0.1325 0.062 Uiso 1 1 calc R . .
C12 C -0.23721(19) 0.3694(3) 0.10872(14) 0.0680(6) Uani 1 1 d . . .
H12A H -0.2734 0.4800 0.0772 0.082 Uiso 1 1 calc R . .
C13 C -0.30804(19) 0.2169(4) 0.12172(14) 0.0717(7) Uani 1 1 d . . .
H13A H -0.3920 0.2230 0.0982 0.086 Uiso 1 1 calc R . .
C14 C -0.25582(19) 0.0555(4) 0.16923(14) 0.0683(6) Uani 1 1 d . . .
H14A H -0.3043 -0.0475 0.1786 0.082 Uiso 1 1 calc R . .
C15 C -0.13120(17) 0.0449(3) 0.20336(13) 0.0527(5) Uani 1 1 d . . .
H15A H -0.0959 -0.0650 0.2359 0.063 Uiso 1 1 calc R . .
C16 C 0.05592(16) 0.1916(2) 0.37580(12) 0.0423(4) Uani 1 1 d . . .


_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 1.306(2) . ?
N1 C1 1.365(2) . ?
N2 C16 1.136(2) . ?
C1 C2 1.410(2) . ?
C1 C6 1.425(2) . ?
C2 C3 1.351(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.402(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.361(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.413(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.419(2) . ?
C7 C8 1.373(2) . ?
C7 C10 1.486(2) . ?
C8 C9 1.417(2) . ?
C8 C16 1.439(2) . ?
C9 H9A 0.9300 . ?
C10 C15 1.384(2) . ?
C10 C11 1.383(2) . ?
C11 C12 1.376(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.365(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.366(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.379(3) . ?
C14 H14A 0.9300 . ?
C15 H15A 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
C9 N1 C1 117.41(16) . . ?
N1 C1 C2 118.26(18) . . ?
N1 C1 C6 122.82(16) . . ?
C2 C1 C6 118.91(19) . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C2 C3 C4 120.40(19) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 C7 123.37(17) . . ?
C5 C6 C1 118.37(16) . . ?
C7 C6 C1 118.25(16) . . ?
C8 C7 C6 117.38(15) . . ?
C8 C7 C10 121.03(15) . . ?
C6 C7 C10 121.59(16) . . ?
C7 C8 C9 120.18(16) . . ?
C7 C8 C16 120.76(16) . . ?
C9 C8 C16 118.98(16) . . ?
N1 C9 C8 123.92(18) . . ?
N1 C9 H9A 118.0 . . ?
C8 C9 H9A 118.0 . . ?
C15 C10 C11 118.95(17) . . ?
C15 C10 C7 120.37(15) . . ?
C11 C10 C7 120.67(15) . . ?
C12 C11 C10 120.05(18) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C10 C15 C14 120.28(19) . . ?
C10 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
N2 C16 C8 179.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.864
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043


####################################################################### 
# 
# 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_pcn
_database_code_depnum_ccdc_archive 'CCDC 1063747'
_audit_update_record             
;
2015-05-07 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H16 N2 O'
_chemical_formula_sum            'C24 H16 N2 O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         348.39

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'
O O 0.0106 0.0060 '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_int_tables_number      14
_chemical_absolute_configuration ?

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                   13.1944(9)
_cell_length_b                   9.7945(10)
_cell_length_c                   14.6162(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.206(7)
_cell_angle_gamma                90.00
_cell_volume                     1859.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1294
_cell_measurement_theta_min      2.9890
_cell_measurement_theta_max      24.6680
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95339
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8872
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         29.26
_reflns_number_total             4363
_reflns_number_gt                2203
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0559P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4363
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1403
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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
O O 0.56370(11) 0.21187(17) 0.23191(9) 0.0606(5) Uani 1 1 d . . .
N1 N 0.53672(13) 0.2516(2) 0.53311(12) 0.0469(5) Uani 1 1 d . . .
H1A H 0.5471(15) 0.261(2) 0.5973(16) 0.068(7) Uiso 1 1 d . . .
N2 N 0.04695(16) -0.0784(3) 0.65426(18) 0.0973(9) Uani 1 1 d . . .
C1 C 0.60267(15) 0.2991(2) 0.47889(13) 0.0427(5) Uani 1 1 d . . .
C2 C 0.56043(15) 0.2627(2) 0.38701(13) 0.0439(5) Uani 1 1 d . . .
C3 C 0.46747(15) 0.1926(2) 0.39048(13) 0.0501(6) Uani 1 1 d . . .
H3A H 0.4233 0.1565 0.3396 0.060 Uiso 1 1 calc R . .
C4 C 0.45314(15) 0.1864(2) 0.48066(13) 0.0451(5) Uani 1 1 d . . .
C5 C 0.69679(15) 0.3720(2) 0.52189(13) 0.0442(5) Uani 1 1 d . . .
C6 C 0.69009(18) 0.4838(3) 0.57801(14) 0.0574(6) Uani 1 1 d . . .
H6A H 0.6262 0.5119 0.5895 0.069 Uiso 1 1 calc R . .
C7 C 0.7776(2) 0.5542(3) 0.61713(17) 0.0767(8) Uani 1 1 d . . .
H7A H 0.7725 0.6297 0.6546 0.092 Uiso 1 1 calc R . .
C8 C 0.8724(2) 0.5131(4) 0.6009(2) 0.0851(9) Uani 1 1 d . . .
H8A H 0.9312 0.5612 0.6269 0.102 Uiso 1 1 calc R . .
C9 C 0.88026(19) 0.4016(3) 0.5464(2) 0.0783(8) Uani 1 1 d . . .
H9A H 0.9445 0.3733 0.5359 0.094 Uiso 1 1 calc R . .
C10 C 0.79279(17) 0.3309(3) 0.50689(15) 0.0574(6) Uani 1 1 d . . .
H10A H 0.7985 0.2550 0.4699 0.069 Uiso 1 1 calc R . .
C11 C 0.60016(15) 0.2819(2) 0.30080(13) 0.0474(6) Uani 1 1 d . . .
C12 C 0.68370(16) 0.3806(2) 0.29402(13) 0.0475(6) Uani 1 1 d . . .
C13 C 0.68508(17) 0.5113(2) 0.33072(14) 0.0552(6) Uani 1 1 d . . .
H13A H 0.6316 0.5405 0.3597 0.066 Uiso 1 1 calc R . .
C14 C 0.7659(2) 0.5980(3) 0.32424(17) 0.0688(7) Uani 1 1 d . . .
H14A H 0.7663 0.6859 0.3483 0.083 Uiso 1 1 calc R . .
C15 C 0.84597(19) 0.5554(3) 0.28238(18) 0.0733(8) Uani 1 1 d . . .
H15A H 0.9011 0.6135 0.2798 0.088 Uiso 1 1 calc R . .
C16 C 0.84440(18) 0.4274(3) 0.24452(18) 0.0711(8) Uani 1 1 d . . .
H16A H 0.8982 0.3989 0.2157 0.085 Uiso 1 1 calc R . .
C17 C 0.76317(17) 0.3406(3) 0.24904(14) 0.0581(6) Uani 1 1 d . . .
H17A H 0.7616 0.2547 0.2218 0.070 Uiso 1 1 calc R . .
C18 C 0.36911(15) 0.1271(2) 0.52042(14) 0.0465(5) Uani 1 1 d . . .
C19 C 0.27424(17) 0.1037(3) 0.46397(16) 0.0691(8) Uani 1 1 d . . .
H19A H 0.2662 0.1237 0.4009 0.083 Uiso 1 1 calc R . .
C20 C 0.19253(17) 0.0521(3) 0.49866(17) 0.0689(8) Uani 1 1 d . . .
H20A H 0.1297 0.0382 0.4595 0.083 Uiso 1 1 calc R . .
C21 C 0.20333(16) 0.0204(2) 0.59233(16) 0.0538(6) Uani 1 1 d . . .
C22 C 0.29710(16) 0.0384(2) 0.64883(15) 0.0567(6) Uani 1 1 d . . .
H22A H 0.3055 0.0148 0.7113 0.068 Uiso 1 1 calc R . .
C23 C 0.37905(16) 0.0914(2) 0.61346(14) 0.0533(6) Uani 1 1 d . . .
H23A H 0.4421 0.1034 0.6527 0.064 Uiso 1 1 calc R . .
C24 C 0.11664(18) -0.0343(3) 0.62810(17) 0.0673(7) Uani 1 1 d . . .


_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
O C11 1.243(2) . ?
N1 C1 1.359(2) . ?
N1 C4 1.382(2) . ?
N1 H1A 0.93(2) . ?
N2 C24 1.141(3) . ?
C1 C2 1.406(2) . ?
C1 C5 1.473(3) . ?
C2 C3 1.415(3) . ?
C2 C11 1.460(3) . ?
C3 C4 1.366(3) . ?
C3 H3A 0.9300 . ?
C4 C18 1.461(3) . ?
C5 C6 1.381(3) . ?
C5 C10 1.383(3) . ?
C6 C7 1.379(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.374(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.366(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.382(3) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.483(3) . ?
C12 C13 1.387(3) . ?
C12 C17 1.389(3) . ?
C13 C14 1.379(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.376(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.369(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.378(3) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.391(3) . ?
C18 C23 1.388(3) . ?
C19 C20 1.367(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.386(3) . ?
C20 H20A 0.9300 . ?
C21 C22 1.372(3) . ?
C21 C24 1.442(3) . ?
C22 C23 1.380(3) . ?
C22 H22A 0.9300 . ?
C23 H23A 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
C1 N1 C4 111.41(17) . . ?
C1 N1 H1A 124.0(13) . . ?
C4 N1 H1A 124.6(13) . . ?
N1 C1 C2 106.48(18) . . ?
N1 C1 C5 119.72(17) . . ?
C2 C1 C5 133.80(18) . . ?
C1 C2 C3 106.77(18) . . ?
C1 C2 C11 130.51(19) . . ?
C3 C2 C11 122.66(18) . . ?
C4 C3 C2 108.98(18) . . ?
C4 C3 H3A 125.5 . . ?
C2 C3 H3A 125.5 . . ?
C3 C4 N1 106.36(18) . . ?
C3 C4 C18 130.26(19) . . ?
N1 C4 C18 123.37(17) . . ?
C6 C5 C10 118.8(2) . . ?
C6 C5 C1 119.99(19) . . ?
C10 C5 C1 121.2(2) . . ?
C5 C6 C7 120.4(2) . . ?
C5 C6 H6A 119.8 . . ?
C7 C6 H6A 119.8 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7A 119.9 . . ?
C8 C7 H7A 119.9 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C8 C9 C10 120.0(3) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C5 C10 C9 120.6(2) . . ?
C5 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
O C11 C2 118.79(19) . . ?
O C11 C12 119.44(18) . . ?
C2 C11 C12 121.76(18) . . ?
C13 C12 C17 118.9(2) . . ?
C13 C12 C11 122.4(2) . . ?
C17 C12 C11 118.7(2) . . ?
C12 C13 C14 119.9(2) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C12 C17 C16 120.5(2) . . ?
C12 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C19 C18 C23 117.3(2) . . ?
C19 C18 C4 119.76(19) . . ?
C23 C18 C4 122.93(18) . . ?
C20 C19 C18 121.8(2) . . ?
C20 C19 H19A 119.1 . . ?
C18 C19 H19A 119.1 . . ?
C19 C20 C21 119.9(2) . . ?
C19 C20 H20A 120.0 . . ?
C21 C20 H20A 120.0 . . ?
C22 C21 C20 119.3(2) . . ?
C22 C21 C24 121.2(2) . . ?
C20 C21 C24 119.4(2) . . ?
C21 C22 C23 120.4(2) . . ?
C21 C22 H22A 119.8 . . ?
C23 C22 H22A 119.8 . . ?
C18 C23 C22 121.18(19) . . ?
C18 C23 H23A 119.4 . . ?
C22 C23 H23A 119.4 . . ?
N2 C24 C21 178.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.861
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.036

