# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_pod236-a_296k_2e
_database_code_depnum_ccdc_archive 'CCDC 1537566'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N2'
_chemical_formula_sum            'C20 H16 N2'
_chemical_formula_weight         284.35

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0562(13)
_cell_length_b                   9.0008(13)
_cell_length_c                   12.130(2)
_cell_angle_alpha                90.532(13)
_cell_angle_beta                 92.165(15)
_cell_angle_gamma                100.461(14)
_cell_volume                     756.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1625
_cell_measurement_theta_min      4.0210
_cell_measurement_theta_max      24.7160

_exptl_crystal_description       'fragment of plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0900 0.0010 -0.0000 0.9916 0.0047 -0.0576 0.0051
1 -1 1 0.1400 0.9942 -0.9930 0.9982 -0.0415 -0.0742 -0.1012
-1 0 -3 0.1150 -0.9959 0.0007 -2.9766 -0.0464 0.1831 0.0803
-5 1 4 0.1550 -4.9604 0.9954 3.9523 -0.0642 -0.1727 0.5098
-1 1 0 0.1500 -0.9932 0.9930 -0.0066 0.0462 0.0166 0.1063
1 2 -2 0.1000 0.9900 1.9842 -1.9908 0.1800 0.1175 -0.0848
1 0 5 0.0850 0.9979 -0.0008 4.9598 0.0559 -0.2984 -0.0701
-1 -1 -6 0.0950 -0.9986 -0.9915 -5.9466 -0.1391 0.3497 0.0543
1 0 1 0.1400 0.9938 -0.0007 0.9934 0.0370 -0.0679 -0.0906
-1 0 -1 0.1300 -0.9938 0.0007 -0.9934 -0.0370 0.0679 0.0906
-1 0 0 0.1300 -0.9928 0.0006 -0.0019 -0.0323 0.0103 0.0957
1 -1 -1 0.2000 0.9922 -0.9930 -0.9850 -0.0510 0.0410 -0.1114
1 0 0 0.1600 0.9928 -0.0006 0.0019 0.0323 -0.0103 -0.0957
0 1 1 0.1100 0.0006 0.9923 0.9869 0.0833 -0.0513 0.0157
0 -1 0 0.0800 0.0004 -0.9924 0.0047 -0.0786 -0.0063 -0.0106
0 1 0 0.0900 -0.0004 0.9924 -0.0047 0.0786 0.0063 0.0106
0 0 -1 0.0950 -0.0010 0.0000 -0.9916 -0.0047 0.0576 -0.0051

_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Sapphire2, large Be window'
_diffrn_detector_area_resol_mean 8.3622

_diffrn_reflns_number            4840
_diffrn_reflns_av_unetI/netI     0.1095
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.746
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_reflns_number_total             3069
_reflns_number_gt                1651
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_orient_matrix_UB_11      0.0325935000
_diffrn_orient_matrix_UB_12      0.0792046000
_diffrn_orient_matrix_UB_13      0.0047156000
_diffrn_orient_matrix_UB_21      -0.0102528000
_diffrn_orient_matrix_UB_22      0.0060695000
_diffrn_orient_matrix_UB_23      -0.0580962000
_diffrn_orient_matrix_UB_31      -0.0964289000
_diffrn_orient_matrix_UB_32      0.0106464000
_diffrn_orient_matrix_UB_33      0.0052790000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00  101.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6530   77.0000  -60.0000 113

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00  101.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6530   77.0000 -180.0000 114

#__ type_ start__ end____ width___ exp.time_
  3 omega  -13.00  101.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6530   77.0000   60.0000 114

;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)


_diffrn_measurement_method       'ω scans'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'WinGx V1.8 (L. J. Farrugia, 1999)'
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0777P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3069
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0709
_refine_ls_wR_factor_ref         0.2152
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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_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 0.2562(3) 0.5371(2) 0.40336(16) 0.0566(6) Uani 1 1 d . . . . .
C2 C 0.3910(4) 0.5563(3) 0.3239(2) 0.0540(6) Uani 1 1 d . . . . .
C3 C 0.4769(3) 0.4319(3) 0.3132(2) 0.0521(6) Uani 1 1 d . . . . .
N4 N 0.3899(3) 0.3315(2) 0.39043(16) 0.0519(6) Uani 1 1 d . . . . .
C5 C 0.4074(4) 0.1843(3) 0.4119(2) 0.0613(7) Uani 1 1 d . . . . .
H5 H 0.4952 0.1388 0.3747 0.074 Uiso 1 1 calc R U . . .
C6 C 0.2959(4) 0.1079(3) 0.4871(2) 0.0677(8) Uani 1 1 d . . . . .
H6 H 0.3092 0.0094 0.5033 0.081 Uiso 1 1 calc R U . . .
C7 C 0.1593(4) 0.1735(3) 0.5419(2) 0.0666(8) Uani 1 1 d . . . . .
H7 H 0.0819 0.1180 0.5930 0.080 Uiso 1 1 calc R U . . .
C8 C 0.1398(4) 0.3181(3) 0.5205(2) 0.0609(7) Uani 1 1 d . . . . .
H8 H 0.0507 0.3626 0.5574 0.073 Uiso 1 1 calc R U . . .
C8A C 0.2555(3) 0.3989(3) 0.44215(19) 0.0487(6) Uani 1 1 d . . . . .
C9 C 0.6237(3) 0.3919(3) 0.2423(2) 0.0530(6) Uani 1 1 d . . . . .
C10 C 0.7872(4) 0.3456(3) 0.2858(2) 0.0671(8) Uani 1 1 d . . . . .
H10 H 0.8064 0.3432 0.3620 0.080 Uiso 1 1 calc R U . . .
C11 C 0.9221(4) 0.3031(3) 0.2191(2) 0.0692(8) Uani 1 1 d . . . . .
H11 H 1.0303 0.2723 0.2509 0.083 Uiso 1 1 calc R U . . .
C12 C 0.8991(4) 0.3055(3) 0.1052(2) 0.0622(7) Uani 1 1 d . . . . .
C13 C 0.7379(4) 0.3540(3) 0.0622(2) 0.0636(7) Uani 1 1 d . . . . .
H13 H 0.7207 0.3581 -0.0141 0.076 Uiso 1 1 calc R U . . .
C14 C 0.6015(4) 0.3965(3) 0.1274(2) 0.0560(7) Uani 1 1 d . . . . .
H14 H 0.4944 0.4284 0.0952 0.067 Uiso 1 1 calc R U . . .
C15 C 1.0425(4) 0.2552(4) 0.0332(3) 0.0869(10) Uani 1 1 d . . . . .
H15A H 0.9920 0.1554 0.0047 0.130 Uiso 1 1 calc R U . . .
H15B H 1.1601 0.2540 0.0754 0.130 Uiso 1 1 calc R U . . .
H15C H 1.0679 0.3236 -0.0269 0.130 Uiso 1 1 calc R U . . .
C16 C 0.4222(4) 0.6989(3) 0.2621(2) 0.0575(7) Uani 1 1 d . . . . .
C17 C 0.5939(4) 0.7549(3) 0.2125(2) 0.0683(8) Uani 1 1 d . . . . .
H17 H 0.6951 0.7015 0.2169 0.082 Uiso 1 1 calc R U . . .
C18 C 0.6153(5) 0.8897(3) 0.1566(2) 0.0836(10) Uani 1 1 d . . . . .
H18 H 0.7309 0.9261 0.1234 0.100 Uiso 1 1 calc R U . . .
C19 C 0.4679(6) 0.9706(3) 0.1495(3) 0.0893(11) Uani 1 1 d . . . . .
H19 H 0.4833 1.0609 0.1114 0.107 Uiso 1 1 calc R U . . .
C20 C 0.2985(6) 0.9174(4) 0.1988(3) 0.0842(10) Uani 1 1 d . . . . .
H20 H 0.1988 0.9723 0.1952 0.101 Uiso 1 1 calc R U . . .
C21 C 0.2754(5) 0.7825(3) 0.2539(2) 0.0695(8) Uani 1 1 d . . . . .
H21 H 0.1589 0.7466 0.2863 0.083 Uiso 1 1 calc R U . . .


_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 C8A 1.333(3) . ?
N1 C2 1.370(3) . ?
C2 C3 1.374(3) . ?
C2 C16 1.478(3) . ?
C3 N4 1.388(3) . ?
C3 C9 1.463(3) . ?
N4 C5 1.379(3) . ?
N4 C8A 1.382(3) . ?
C5 C6 1.339(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.403(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.360(4) . ?
C7 H7 0.9300 . ?
C8 C8A 1.398(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(3) . ?
C9 C14 1.398(3) . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(4) . ?
C12 C15 1.489(4) . ?
C13 C14 1.372(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.387(4) . ?
C16 C21 1.387(4) . ?
C17 C18 1.383(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(4) . ?
C20 H20 0.9300 . ?
C21 H21 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
C8A N1 C2 105.5(2) . . ?
N1 C2 C3 111.8(2) . . ?
N1 C2 C16 118.7(2) . . ?
C3 C2 C16 129.5(2) . . ?
C2 C3 N4 104.5(2) . . ?
C2 C3 C9 134.5(2) . . ?
N4 C3 C9 121.0(2) . . ?
C5 N4 C8A 121.2(2) . . ?
C5 N4 C3 130.9(2) . . ?
C8A N4 C3 107.61(19) . . ?
C6 C5 N4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
N4 C5 H5 120.5 . . ?
C5 C6 C7 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C8A 119.0(3) . . ?
C7 C8 H8 120.5 . . ?
C8A C8 H8 120.5 . . ?
N1 C8A N4 110.6(2) . . ?
N1 C8A C8 130.1(2) . . ?
N4 C8A C8 119.3(2) . . ?
C10 C9 C14 117.6(2) . . ?
C10 C9 C3 121.5(2) . . ?
C14 C9 C3 120.9(2) . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 117.3(2) . . ?
C13 C12 C15 121.9(3) . . ?
C11 C12 C15 120.8(3) . . ?
C14 C13 C12 122.6(3) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C13 C14 C9 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.9(3) . . ?
C17 C16 C2 122.8(3) . . ?
C21 C16 C2 119.2(3) . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.0(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 121.5(3) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.057


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
