# Electronic Supplementary Material (ESI) for Analyst.
# This journal is © The Royal Society of Chemistry 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
#  on your local computer system.
# 
#  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_ps119_0ma

_audit_creation_date             2013-06-13T23:12:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C20 H15 N3 O'
_chemical_formula_weight         313.36
_chemical_absolute_configuration unk

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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.3994(12)
_cell_length_b                   14.277(4)
_cell_length_c                   20.499(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1580.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

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

_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_unetI/netI     0.1946
_diffrn_reflns_number            8503
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         27.67
_diffrn_reflns_theta_full        27.67
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_reflns_number_total             3602
_reflns_number_gt                1282
_reflns_threshold_expression     >2sigma(I)

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

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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)+(0.0439P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3602
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2337
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.1656
_refine_ls_wR_factor_gt          0.114
_refine_ls_goodness_of_fit_ref   0.93
_refine_ls_restrained_S_all      0.93
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -6(5)
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   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 0.003 0.002 '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 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.011 0.006 '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 0.5627(9) 0.8441(4) 0.1696(3) 0.0561(15) Uani 1 1 d . . .
C2 C 0.7560(10) 0.8985(4) 0.1947(3) 0.0638(16) Uani 1 1 d . . .
H2 H 0.7819 0.9587 0.1787 0.077 Uiso 1 1 calc R . .
C3 C 0.9051(10) 0.8645(4) 0.2419(3) 0.0661(17) Uani 1 1 d . . .
H3 H 1.0364 0.9006 0.2571 0.079 Uiso 1 1 calc R . .
C4 C 0.8642(9) 0.7755(4) 0.2684(2) 0.0540(14) Uani 1 1 d . . .
C5 C 1.0226(10) 0.7398(4) 0.3180(3) 0.0659(16) Uani 1 1 d . . .
H5 H 1.1547 0.7757 0.3328 0.079 Uiso 1 1 calc R . .
C6 C 0.9817(11) 0.6520(4) 0.3443(3) 0.0700(17) Uani 1 1 d . . .
H6 H 1.0876 0.6289 0.3763 0.084 Uiso 1 1 calc R . .
C7 C 0.7847(10) 0.5986(4) 0.3234(3) 0.0646(16) Uani 1 1 d . . .
H7 H 0.7552 0.5403 0.3422 0.078 Uiso 1 1 calc R . .
C8 C 0.6314(9) 0.6309(4) 0.2748(2) 0.0566(15) Uani 1 1 d . . .
H8 H 0.5011 0.5935 0.2606 0.068 Uiso 1 1 calc R . .
C9 C 0.6678(9) 0.7203(3) 0.2459(2) 0.0496(13) Uani 1 1 d . . .
C10 C 0.5107(9) 0.7559(3) 0.1947(2) 0.0457(12) Uani 1 1 d . . .
C11 C 0.3095(9) 0.7015(3) 0.1683(2) 0.0506(14) Uani 1 1 d . . .
H11 H 0.2753 0.6427 0.1856 0.061 Uiso 1 1 calc R . .
C12 C -0.0228(8) 0.6828(3) 0.0947(2) 0.0428(12) Uani 1 1 d . . .
C13 C -0.1122(9) 0.5928(3) 0.1047(2) 0.0502(13) Uani 1 1 d . . .
H13 H -0.049 0.5478 0.1329 0.06 Uiso 1 1 calc R . .
C14 C -0.3117(9) 0.5843(3) 0.0645(2) 0.0441(12) Uani 1 1 d . . .
C15 C -0.4811(9) 0.5077(3) 0.0499(2) 0.0498(13) Uani 1 1 d . . .
C16 C -0.4620(10) 0.4253(4) 0.0857(3) 0.0674(16) Uani 1 1 d . . .
H16 H -0.341 0.4203 0.1178 0.081 Uiso 1 1 calc R . .
C17 C -0.6188(12) 0.3509(4) 0.0746(3) 0.0808(18) Uani 1 1 d . . .
H17 H -0.6013 0.2959 0.0984 0.097 Uiso 1 1 calc R . .
C18 C -0.8008(12) 0.3583(4) 0.0283(3) 0.0750(18) Uani 1 1 d . . .
H18 H -0.9077 0.3083 0.0208 0.09 Uiso 1 1 calc R . .
C19 C -0.8251(11) 0.4387(4) -0.0068(3) 0.0704(16) Uani 1 1 d . . .
H19 H -0.9497 0.4437 -0.0379 0.085 Uiso 1 1 calc R . .
C20 C -0.6659(10) 0.5127(4) 0.0035(2) 0.0601(15) Uani 1 1 d . . .
H20 H -0.6833 0.5669 -0.0212 0.072 Uiso 1 1 calc R . .
N1 N 0.1757(7) 0.7336(3) 0.12089(19) 0.0498(10) Uani 1 1 d . . .
N2 N -0.1563(7) 0.7299(3) 0.05078(18) 0.0499(11) Uani 1 1 d . . .
N3 N -0.3315(7) 0.6682(3) 0.03292(18) 0.0492(11) Uani 1 1 d . . .
H3A H -0.4444 0.6803 0.0046 0.059 Uiso 1 1 calc R . .
O1 O 0.4235(6) 0.8836(2) 0.12253(17) 0.0676(11) Uani 1 1 d . . .
H1 H 0.3562 0.8424 0.101 0.081 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 O1 1.348(6) . ?
C1 C10 1.388(6) . ?
C1 C2 1.399(7) . ?
C2 C3 1.350(7) . ?
C2 H2 0.93 . ?
C3 C4 1.399(6) . ?
C3 H3 0.93 . ?
C4 C9 1.400(6) . ?
C4 C5 1.423(7) . ?
C5 C6 1.382(7) . ?
C5 H5 0.93 . ?
C6 C7 1.378(7) . ?
C6 H6 0.93 . ?
C7 C8 1.375(6) . ?
C7 H7 0.93 . ?
C8 C9 1.421(6) . ?
C8 H8 0.93 . ?
C9 C10 1.442(6) . ?
C10 C11 1.441(6) . ?
C11 N1 1.295(5) . ?
C11 H11 0.93 . ?
C12 N2 1.335(5) . ?
C12 C13 1.387(6) . ?
C12 N1 1.402(6) . ?
C13 C14 1.362(6) . ?
C13 H13 0.93 . ?
C14 N3 1.365(5) . ?
C14 C15 1.456(6) . ?
C15 C20 1.381(6) . ?
C15 C16 1.389(6) . ?
C16 C17 1.377(7) . ?
C16 H16 0.93 . ?
C17 C18 1.370(8) . ?
C17 H17 0.93 . ?
C18 C19 1.361(7) . ?
C18 H18 0.93 . ?
C19 C20 1.378(6) . ?
C19 H19 0.93 . ?
C20 H20 0.93 . ?
N2 N3 1.343(5) . ?
N3 H3A 0.86 . ?
O1 H1 0.82 . ?

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
O1 C1 C10 122.1(5) . . ?
O1 C1 C2 116.6(5) . . ?
C10 C1 C2 121.2(5) . . ?
C3 C2 C1 120.6(5) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.7(5) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C9 120.2(5) . . ?
C3 C4 C5 120.6(6) . . ?
C9 C4 C5 119.2(5) . . ?
C6 C5 C4 120.6(6) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 120.2(6) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C6 120.3(5) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 121.4(5) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C4 C9 C8 118.3(5) . . ?
C4 C9 C10 119.1(5) . . ?
C8 C9 C10 122.6(5) . . ?
C1 C10 C11 120.2(5) . . ?
C1 C10 C9 118.1(5) . . ?
C11 C10 C9 121.8(4) . . ?
N1 C11 C10 120.8(5) . . ?
N1 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
N2 C12 C13 112.2(4) . . ?
N2 C12 N1 114.3(4) . . ?
C13 C12 N1 133.5(5) . . ?
C14 C13 C12 105.6(4) . . ?
C14 C13 H13 127.2 . . ?
C12 C13 H13 127.2 . . ?
C13 C14 N3 105.7(4) . . ?
C13 C14 C15 133.4(5) . . ?
N3 C14 C15 120.9(4) . . ?
C20 C15 C16 117.5(5) . . ?
C20 C15 C14 123.7(5) . . ?
C16 C15 C14 118.8(5) . . ?
C17 C16 C15 121.3(5) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 119.8(6) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.0(6) . . ?
C19 C18 H18 120 . . ?
C17 C18 H18 120 . . ?
C18 C19 C20 120.4(5) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 121.1(5) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C11 N1 C12 122.1(4) . . ?
C12 N2 N3 103.5(4) . . ?
N2 N3 C14 113.0(4) . . ?
N2 N3 H3A 123.5 . . ?
C14 N3 H3A 123.5 . . ?
C1 O1 H1 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
O1 C1 C2 C3 -179.9(5) . . . . ?
C10 C1 C2 C3 3.3(8) . . . . ?
C1 C2 C3 C4 -2.3(8) . . . . ?
C2 C3 C4 C9 0.3(7) . . . . ?
C2 C3 C4 C5 179.7(5) . . . . ?
C3 C4 C5 C6 179.7(5) . . . . ?
C9 C4 C5 C6 -0.9(7) . . . . ?
C4 C5 C6 C7 -0.8(8) . . . . ?
C5 C6 C7 C8 1.9(8) . . . . ?
C6 C7 C8 C9 -1.3(8) . . . . ?
C3 C4 C9 C8 -179.2(5) . . . . ?
C5 C4 C9 C8 1.4(7) . . . . ?
C3 C4 C9 C10 0.7(7) . . . . ?
C5 C4 C9 C10 -178.7(4) . . . . ?
C7 C8 C9 C4 -0.4(7) . . . . ?
C7 C8 C9 C10 179.8(5) . . . . ?
O1 C1 C10 C11 2.9(7) . . . . ?
C2 C1 C10 C11 179.6(4) . . . . ?
O1 C1 C10 C9 -178.9(4) . . . . ?
C2 C1 C10 C9 -2.3(7) . . . . ?
C4 C9 C10 C1 0.3(6) . . . . ?
C8 C9 C10 C1 -179.9(4) . . . . ?
C4 C9 C10 C11 178.4(4) . . . . ?
C8 C9 C10 C11 -1.7(7) . . . . ?
C1 C10 C11 N1 0.4(7) . . . . ?
C9 C10 C11 N1 -177.7(4) . . . . ?
N2 C12 C13 C14 0.1(5) . . . . ?
N1 C12 C13 C14 180.0(5) . . . . ?
C12 C13 C14 N3 0.0(5) . . . . ?
C12 C13 C14 C15 177.6(5) . . . . ?
C13 C14 C15 C20 -175.8(5) . . . . ?
N3 C14 C15 C20 1.5(7) . . . . ?
C13 C14 C15 C16 6.0(8) . . . . ?
N3 C14 C15 C16 -176.7(4) . . . . ?
C20 C15 C16 C17 1.0(8) . . . . ?
C14 C15 C16 C17 179.3(5) . . . . ?
C15 C16 C17 C18 -1.2(9) . . . . ?
C16 C17 C18 C19 0.4(9) . . . . ?
C17 C18 C19 C20 0.6(9) . . . . ?
C18 C19 C20 C15 -0.8(8) . . . . ?
C16 C15 C20 C19 0.0(7) . . . . ?
C14 C15 C20 C19 -178.2(4) . . . . ?
C10 C11 N1 C12 -179.3(4) . . . . ?
N2 C12 N1 C11 173.5(4) . . . . ?
C13 C12 N1 C11 -6.4(8) . . . . ?
C13 C12 N2 N3 -0.2(5) . . . . ?
N1 C12 N2 N3 179.9(3) . . . . ?
C12 N2 N3 C14 0.2(5) . . . . ?
C13 C14 N3 N2 -0.1(5) . . . . ?
C15 C14 N3 N2 -178.1(4) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 994856'
