# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_PYRE
_database_code_depnum_ccdc_archive 'CCDC 1586465'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-04-13 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         'C23 H14 N2'

_chemical_formula_sum            'C23 H14 N2'
_chemical_formula_weight         318.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   8.78730(10)
_cell_length_b                   9.66370(10)
_cell_length_c                   36.9535(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3138.01(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7470
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      71.91

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.618
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6664
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a

_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex3 CMOS Diffractometer'
_diffrn_measurement_method       'ω and φ scan'



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22409
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0626
_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       -45
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         5.575
_diffrn_reflns_theta_max         72.223
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3075
_reflns_number_gt                2455
_reflns_threshold_expression     'I > 2σ(I)'
_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       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'




_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+0.8182P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3075
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C -0.07661(19) 0.66917(15) 0.28939(4) 0.0456(4) Uani 1 1 d . . . . .
H1 H -0.1007 0.5756 0.2908 0.055 Uiso 1 1 calc R U . . .
C2 C -0.16563(19) 0.75944(17) 0.26971(4) 0.0501(4) Uani 1 1 d . . . . .
H2 H -0.2502 0.7259 0.2574 0.060 Uiso 1 1 calc R U . . .
C3 C -0.13091(19) 0.90044(16) 0.26794(4) 0.0476(4) Uani 1 1 d . . . . .
H3 H -0.1926 0.9586 0.2543 0.057 Uiso 1 1 calc R U . . .
C4 C -0.00774(19) 0.95551(15) 0.28595(4) 0.0440(4) Uani 1 1 d . . . . .
H4 H 0.0136 1.0497 0.2853 0.053 Uiso 1 1 calc R U . . .
C5 C 0.08302(16) 0.86346(14) 0.30513(4) 0.0352(3) Uani 1 1 d . . . . .
C6 C 0.05015(16) 0.72201(13) 0.30711(4) 0.0353(3) Uani 1 1 d . . . . .
C7 C 0.25881(17) 0.75436(14) 0.33655(4) 0.0355(3) Uani 1 1 d . . . . .
C8 C 0.40453(17) 0.73327(14) 0.35542(4) 0.0378(3) Uani 1 1 d . . . . .
C9 C 0.53045(18) 0.80666(16) 0.34282(5) 0.0473(4) Uani 1 1 d . . . . .
H9 H 0.5173 0.8716 0.3245 0.057 Uiso 1 1 calc R U . . .
C10 C 0.67393(18) 0.78534(17) 0.35683(5) 0.0511(4) Uani 1 1 d . . . . .
H10 H 0.7556 0.8367 0.3481 0.061 Uiso 1 1 calc R U . . .
C11 C 0.69760(17) 0.68768(17) 0.38391(4) 0.0458(4) Uani 1 1 d . . . . .
C12 C 0.8464(2) 0.6577(2) 0.39780(5) 0.0604(5) Uani 1 1 d . . . . .
H12 H 0.9305 0.7024 0.3880 0.072 Uiso 1 1 calc R U . . .
C13 C 0.8664(2) 0.5658(2) 0.42477(5) 0.0657(5) Uani 1 1 d . . . . .
H13 H 0.9644 0.5481 0.4331 0.079 Uiso 1 1 calc R U . . .
C14 C 0.7413(2) 0.4952(2) 0.44083(5) 0.0556(4) Uani 1 1 d . . . . .
C15 C 0.7589(2) 0.4033(2) 0.46977(5) 0.0728(6) Uani 1 1 d . . . . .
H15 H 0.8556 0.3865 0.4790 0.087 Uiso 1 1 calc R U . . .
C16 C 0.6354(3) 0.3374(3) 0.48482(6) 0.0806(7) Uani 1 1 d . . . . .
H16 H 0.6494 0.2774 0.5042 0.097 Uiso 1 1 calc R U . . .
C17 C 0.4914(2) 0.3593(2) 0.47144(6) 0.0737(6) Uani 1 1 d . . . . .
H17 H 0.4092 0.3137 0.4819 0.088 Uiso 1 1 calc R U . . .
C18 C 0.4668(2) 0.44915(19) 0.44239(5) 0.0541(4) Uani 1 1 d . . . . .
C19 C 0.3192(2) 0.4758(2) 0.42787(5) 0.0586(5) Uani 1 1 d . . . . .
H19 H 0.2357 0.4300 0.4376 0.070 Uiso 1 1 calc R U . . .
C20 C 0.29712(18) 0.56555(17) 0.40037(4) 0.0483(4) Uani 1 1 d . . . . .
H20 H 0.1990 0.5805 0.3918 0.058 Uiso 1 1 calc R U . . .
C21 C 0.42208(17) 0.63840(15) 0.38411(4) 0.0379(3) Uani 1 1 d . . . . .
C22 C 0.57063(17) 0.61513(15) 0.39816(4) 0.0408(4) Uani 1 1 d . . . . .
C23 C 0.59256(18) 0.51947(17) 0.42710(4) 0.0462(4) Uani 1 1 d . . . . .
N1 N 0.16190(14) 0.65541(11) 0.32724(3) 0.0377(3) Uani 1 1 d . . . . .
N2 N 0.21640(14) 0.88078(12) 0.32400(3) 0.0382(3) Uani 1 1 d . . . . .
H1B H 0.268(2) 0.9635(18) 0.3278(4) 0.052(5) Uiso 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
C1 C2 1.379(2) . ?
C1 C6 1.389(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.398(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9300 . ?
C5 N2 1.3740(19) . ?
C5 C6 1.3991(19) . ?
C6 N1 1.3898(18) . ?
C7 N1 1.3260(18) . ?
C7 N2 1.3589(17) . ?
C7 C8 1.472(2) . ?
C8 C9 1.394(2) . ?
C8 C21 1.410(2) . ?
C9 C10 1.378(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(2) . ?
C10 H10 0.9300 . ?
C11 C22 1.419(2) . ?
C11 C12 1.434(2) . ?
C12 C13 1.346(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.424(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.399(3) . ?
C14 C23 1.422(2) . ?
C15 C16 1.376(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.397(2) . ?
C17 H17 0.9300 . ?
C18 C23 1.415(2) . ?
C18 C19 1.427(2) . ?
C19 C20 1.350(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.436(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.423(2) . ?
C22 C23 1.427(2) . ?
N2 H1B 0.931(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.09(14) . . ?
C2 C1 H1 121.0 . . ?
C6 C1 H1 121.0 . . ?
C1 C2 C3 121.16(15) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 121.70(14) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 116.76(14) . . ?
C3 C4 H4 121.6 . . ?
C5 C4 H4 121.6 . . ?
N2 C5 C4 132.12(13) . . ?
N2 C5 C6 105.58(12) . . ?
C4 C5 C6 122.27(14) . . ?
C1 C6 N1 130.43(13) . . ?
C1 C6 C5 119.99(13) . . ?
N1 C6 C5 109.55(12) . . ?
N1 C7 N2 112.56(12) . . ?
N1 C7 C8 125.57(12) . . ?
N2 C7 C8 121.65(13) . . ?
C9 C8 C21 119.66(14) . . ?
C9 C8 C7 117.51(13) . . ?
C21 C8 C7 122.77(13) . . ?
C10 C9 C8 121.64(15) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 120.55(15) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C22 118.98(14) . . ?
C10 C11 C12 122.07(15) . . ?
C22 C11 C12 118.95(15) . . ?
C13 C12 C11 121.17(17) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 121.58(17) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C23 118.64(18) . . ?
C15 C14 C13 122.53(18) . . ?
C23 C14 C13 118.83(16) . . ?
C16 C15 C14 121.06(18) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 120.59(18) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 121.0(2) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C23 118.97(17) . . ?
C17 C18 C19 122.79(17) . . ?
C23 C18 C19 118.23(15) . . ?
C20 C19 C18 121.97(16) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C19 C20 C21 121.33(15) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C8 C21 C22 118.52(14) . . ?
C8 C21 C20 123.34(14) . . ?
C22 C21 C20 118.12(13) . . ?
C11 C22 C21 120.52(14) . . ?
C11 C22 C23 119.48(14) . . ?
C21 C22 C23 120.00(14) . . ?
C18 C23 C14 119.75(15) . . ?
C18 C23 C22 120.34(14) . . ?
C14 C23 C22 119.91(15) . . ?
C7 N1 C6 104.99(11) . . ?
C7 N2 C5 107.32(12) . . ?
C7 N2 H1B 125.9(10) . . ?
C5 N2 H1B 126.8(10) . . ?

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
C6 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
C3 C4 C5 N2 175.76(15) . . . . ?
C3 C4 C5 C6 -1.7(2) . . . . ?
C2 C1 C6 N1 -176.87(15) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
N2 C5 C6 C1 -177.71(13) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
N2 C5 C6 N1 0.53(16) . . . . ?
C4 C5 C6 N1 178.54(13) . . . . ?
N1 C7 C8 C9 136.27(16) . . . . ?
N2 C7 C8 C9 -37.9(2) . . . . ?
N1 C7 C8 C21 -40.7(2) . . . . ?
N2 C7 C8 C21 145.11(14) . . . . ?
C21 C8 C9 C10 2.4(2) . . . . ?
C7 C8 C9 C10 -174.66(15) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C22 -3.1(3) . . . . ?
C9 C10 C11 C12 176.71(17) . . . . ?
C10 C11 C12 C13 177.98(18) . . . . ?
C22 C11 C12 C13 -2.2(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 -177.5(2) . . . . ?
C12 C13 C14 C23 2.1(3) . . . . ?
C23 C14 C15 C16 0.0(3) . . . . ?
C13 C14 C15 C16 179.6(2) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C16 C17 C18 C23 -0.9(3) . . . . ?
C16 C17 C18 C19 -179.4(2) . . . . ?
C17 C18 C19 C20 178.33(19) . . . . ?
C23 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C9 C8 C21 C22 -3.3(2) . . . . ?
C7 C8 C21 C22 173.68(13) . . . . ?
C9 C8 C21 C20 175.64(15) . . . . ?
C7 C8 C21 C20 -7.4(2) . . . . ?
C19 C20 C21 C8 -179.85(16) . . . . ?
C19 C20 C21 C22 -1.0(2) . . . . ?
C10 C11 C22 C21 2.2(2) . . . . ?
C12 C11 C22 C21 -177.63(15) . . . . ?
C10 C11 C22 C23 -177.09(15) . . . . ?
C12 C11 C22 C23 3.1(2) . . . . ?
C8 C21 C22 C11 1.0(2) . . . . ?
C20 C21 C22 C11 -177.96(14) . . . . ?
C8 C21 C22 C23 -179.77(14) . . . . ?
C20 C21 C22 C23 1.3(2) . . . . ?
C17 C18 C23 C14 1.6(3) . . . . ?
C19 C18 C23 C14 -179.83(17) . . . . ?
C17 C18 C23 C22 -178.05(18) . . . . ?
C19 C18 C23 C22 0.5(3) . . . . ?
C15 C14 C23 C18 -1.1(3) . . . . ?
C13 C14 C23 C18 179.28(17) . . . . ?
C15 C14 C23 C22 178.50(17) . . . . ?
C13 C14 C23 C22 -1.1(3) . . . . ?
C11 C22 C23 C18 178.14(15) . . . . ?
C21 C22 C23 C18 -1.1(2) . . . . ?
C11 C22 C23 C14 -1.5(2) . . . . ?
C21 C22 C23 C14 179.27(15) . . . . ?
N2 C7 N1 C6 0.48(16) . . . . ?
C8 C7 N1 C6 -174.14(13) . . . . ?
C1 C6 N1 C7 177.38(16) . . . . ?
C5 C6 N1 C7 -0.62(16) . . . . ?
N1 C7 N2 C5 -0.16(17) . . . . ?
C8 C7 N2 C5 174.70(12) . . . . ?
C4 C5 N2 C7 -177.96(16) . . . . ?
C6 C5 N2 C7 -0.24(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1B N1 0.931(17) 1.954(18) 2.8638(16) 165.4(15) 8_665

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.030

