# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_PS144


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H16 N4'
_chemical_formula_sum            'C16 H16 N4'
_chemical_formula_weight         264.33
_chemical_compound_source        'synthesis as described'

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

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

_cell_length_a                   5.7857(5)
_cell_length_b                   16.921(2)
_cell_length_c                   13.7060(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.453(4)
_cell_angle_gamma                90
_cell_volume                     1327.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3366
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.34
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  0.993


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

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_number            11435
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.76
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             3038
_reflns_number_gt                2515
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 2012),
           CRYSCAL (T. Roisnel, local program)
;

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 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)+(0.0470P)²+0.4053P] 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_number_reflns         3038
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.044

# End of res file
#----------------------------------------------------------------------------#

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4721(2) 0.19391(8) -0.18914(10) 0.0245(3) Uani 1 1 d . . .
H1 H 0.3275 0.1681 -0.1861 0.029 Uiso 1 1 calc R . .
C2 C 0.4939(2) 0.24414(9) -0.26737(10) 0.0290(3) Uani 1 1 d . . .
H2 H 0.3645 0.2525 -0.3176 0.035 Uiso 1 1 calc R . .
C3 C 0.7052(2) 0.28224(8) -0.27234(10) 0.0279(3) Uani 1 1 d . . .
H3 H 0.7193 0.3178 -0.3247 0.033 Uiso 1 1 calc R . .
C4 C 0.8947(2) 0.26782(8) -0.20029(10) 0.0258(3) Uani 1 1 d . . .
H4 H 1.0403 0.2926 -0.2045 0.031 Uiso 1 1 calc R . .
C5 C 0.8738(2) 0.21764(7) -0.12220(10) 0.0227(3) Uani 1 1 d . . .
H5 H 1.0052 0.2081 -0.0733 0.027 Uiso 1 1 calc R . .
C6 C 0.6608(2) 0.18105(7) -0.11494(9) 0.0196(3) Uani 1 1 d . . .
C7 C 0.6310(2) 0.13195(7) -0.02905(9) 0.0190(3) Uani 1 1 d . . .
N8 N 0.41426(19) 0.11726(7) -0.00460(8) 0.0229(3) Uani 1 1 d . . .
N9 N 0.43670(19) 0.07473(7) 0.07642(8) 0.0230(3) Uani 1 1 d . . .
N10 N 0.66811(18) 0.06246(6) 0.10475(8) 0.0191(2) Uani 1 1 d . . .
C11 C 0.7938(2) 0.09688(7) 0.04070(9) 0.0203(3) Uani 1 1 d . . .
H11 H 0.9588 0.0968 0.0433 0.024 Uiso 1 1 calc R . .
C12 C 0.7471(2) 0.02002(7) 0.19363(9) 0.0196(3) Uani 1 1 d . . .
C13 C 0.9560(2) -0.02172(8) 0.20460(10) 0.0224(3) Uani 1 1 d . . .
H13 H 1.0481 -0.0223 0.1526 0.027 Uiso 1 1 calc R . .
C14 C 1.0303(2) -0.06245(8) 0.29102(10) 0.0232(3) Uani 1 1 d . . .
H14 H 1.1727 -0.0912 0.2974 0.028 Uiso 1 1 calc R . .
C15 C 0.8992(2) -0.06213(7) 0.36969(9) 0.0220(3) Uani 1 1 d . . .
C16 C 0.6868(2) -0.02038(8) 0.35562(10) 0.0245(3) Uani 1 1 d . . .
H16 H 0.5921 -0.0201 0.4067 0.029 Uiso 1 1 calc R . .
C17 C 0.6124(2) 0.02035(8) 0.26909(10) 0.0229(3) Uani 1 1 d . . .
H17 H 0.4689 0.0485 0.2615 0.027 Uiso 1 1 calc R . .
N18 N 0.9792(2) -0.09865(7) 0.45877(9) 0.0290(3) Uani 1 1 d . . .
C19 C 1.1574(3) -0.15858(11) 0.46515(12) 0.0423(4) Uani 1 1 d . . .
H19A H 1.0904 -0.2074 0.4346 0.063 Uiso 1 1 calc R . .
H19B H 1.2184 -0.1686 0.5346 0.063 Uiso 1 1 calc R . .
H19C H 1.2845 -0.1406 0.4306 0.063 Uiso 1 1 calc R . .
C20 C 0.8266(3) -0.10311(9) 0.53346(10) 0.0308(3) Uani 1 1 d . . .
H20A H 0.7749 -0.0498 0.5481 0.046 Uiso 1 1 calc R . .
H20B H 0.9114 -0.1268 0.5936 0.046 Uiso 1 1 calc R . .
H20C H 0.6903 -0.1358 0.5092 0.046 Uiso 1 1 calc R . .





#----------------------------------------------------------------------------#
#                   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
C1 C2 1.3884(19) . ?
C1 C6 1.3955(18) . ?
C1 H1 0.95 . ?
C2 C3 1.393(2) . ?
C2 H2 0.95 . ?
C3 C4 1.385(2) . ?
C3 H3 0.95 . ?
C4 C5 1.3855(18) . ?
C4 H4 0.95 . ?
C5 C6 1.3958(18) . ?
C5 H5 0.95 . ?
C6 C7 1.4715(17) . ?
C7 N8 1.3676(16) . ?
C7 C11 1.3742(18) . ?
N8 N9 1.3135(15) . ?
N9 N10 1.3541(15) . ?
N10 C11 1.3515(16) . ?
N10 C12 1.4300(16) . ?
C11 H11 0.95 . ?
C12 C17 1.3833(18) . ?
C12 C13 1.3890(18) . ?
C13 C14 1.3832(18) . ?
C13 H13 0.95 . ?
C14 C15 1.4063(18) . ?
C14 H14 0.95 . ?
C15 N18 1.3858(16) . ?
C15 C16 1.4062(18) . ?
C16 C17 1.3844(18) . ?
C16 H16 0.95 . ?
C17 H17 0.95 . ?
N18 C19 1.4393(19) . ?
N18 C20 1.4487(18) . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?


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 120.54(13) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 120.08(13) . . ?
C1 C2 H2 120 . . ?
C3 C2 H2 120 . . ?
C4 C3 C2 119.49(13) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.59(12) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.34(12) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.91(12) . . ?
C1 C6 C7 119.99(11) . . ?
C5 C6 C7 121.06(11) . . ?
N8 C7 C11 108.09(11) . . ?
N8 C7 C6 121.21(11) . . ?
C11 C7 C6 130.64(12) . . ?
N9 N8 C7 109.06(10) . . ?
N8 N9 N10 107.28(10) . . ?
C11 N10 N9 110.57(10) . . ?
C11 N10 C12 129.41(11) . . ?
N9 N10 C12 119.99(10) . . ?
N10 C11 C7 104.99(11) . . ?
N10 C11 H11 127.5 . . ?
C7 C11 H11 127.5 . . ?
C17 C12 C13 119.87(12) . . ?
C17 C12 N10 119.37(11) . . ?
C13 C12 N10 120.76(11) . . ?
C14 C13 C12 120.13(12) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 121.34(12) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
N18 C15 C16 121.12(12) . . ?
N18 C15 C14 121.73(12) . . ?
C16 C15 C14 117.11(12) . . ?
C17 C16 C15 121.53(12) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C12 C17 C16 120.02(12) . . ?
C12 C17 H17 120 . . ?
C16 C17 H17 120 . . ?
C15 N18 C19 120.74(12) . . ?
C15 N18 C20 119.10(12) . . ?
C19 N18 C20 115.20(12) . . ?
N18 C19 H19A 109.5 . . ?
N18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N18 C20 H20A 109.5 . . ?
N18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?


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 0.0(2) . . . . ?
C1 C2 C3 C4 1.9(2) . . . . ?
C2 C3 C4 C5 -1.8(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C2 C1 C6 C5 -1.91(19) . . . . ?
C2 C1 C6 C7 175.88(12) . . . . ?
C4 C5 C6 C1 2.02(19) . . . . ?
C4 C5 C6 C7 -175.75(12) . . . . ?
C1 C6 C7 N8 -19.20(18) . . . . ?
C5 C6 C7 N8 158.54(12) . . . . ?
C1 C6 C7 C11 163.96(13) . . . . ?
C5 C6 C7 C11 -18.3(2) . . . . ?
C11 C7 N8 N9 -0.22(14) . . . . ?
C6 C7 N8 N9 -177.69(11) . . . . ?
C7 N8 N9 N10 0.46(14) . . . . ?
N8 N9 N10 C11 -0.55(14) . . . . ?
N8 N9 N10 C12 177.66(10) . . . . ?
N9 N10 C11 C7 0.41(14) . . . . ?
C12 N10 C11 C7 -177.58(11) . . . . ?
N8 C7 C11 N10 -0.12(14) . . . . ?
C6 C7 C11 N10 177.04(12) . . . . ?
C11 N10 C12 C17 150.94(13) . . . . ?
N9 N10 C12 C17 -26.89(17) . . . . ?
C11 N10 C12 C13 -29.46(19) . . . . ?
N9 N10 C12 C13 152.71(12) . . . . ?
C17 C12 C13 C14 -0.45(19) . . . . ?
N10 C12 C13 C14 179.95(11) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 N18 -175.91(12) . . . . ?
C13 C14 C15 C16 1.63(19) . . . . ?
N18 C15 C16 C17 175.97(12) . . . . ?
C14 C15 C16 C17 -1.59(19) . . . . ?
C13 C12 C17 C16 0.49(19) . . . . ?
N10 C12 C17 C16 -179.90(12) . . . . ?
C15 C16 C17 C12 0.6(2) . . . . ?
C16 C15 N18 C19 162.51(14) . . . . ?
C14 C15 N18 C19 -20.0(2) . . . . ?
C16 C15 N18 C20 8.63(19) . . . . ?
C14 C15 N18 C20 -173.92(12) . . . . ?
#----------------------------------------------------------------------------#
# END OF CIF FILE FOR PS144                                                  #
#----------------------------------------------------------------------------#

##############################################################################
# END OF GLOBAL CIF FILE                                                     #
##############################################################################



_database_code_depnum_ccdc_archive 'CCDC 984548'
