# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_13a_dh_form_vlt_p
_database_code_depnum_ccdc_archive 'CCDC 970533'
_audit_update_record             
;
2013-11-06 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;


_audit_creation_date             2013-10-31T14:02:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O'
_chemical_formula_sum            'C14 H13 N3 O'
_chemical_formula_weight         239.27

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'
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                   13.488(2)
_cell_length_b                   9.6611(15)
_cell_length_c                   9.3604(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.183(5)
_cell_angle_gamma                90
_cell_volume                     1219.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6777
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      28.28

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -1 0.184
0 1 1 0.156
-1 -2 2 0.123
0 1 0 0.111
0 -1 0 0.181
-1 0 0 0.019
1 0 0 0.022
0 0 -1 0.189
0 0 1 0.157

_exptl_special_details           ?

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

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.9966

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.069
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_number            20120
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_reflns_number_total             2900
_reflns_number_gt                1992
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX3 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

#----------------------------------------------------------------------------#
#                   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)+(0.1353P)²+0.8927P] 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_number_reflns         2900
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2468
_refine_ls_wR_factor_gt          0.1936
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.11

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 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 0.26804(18) 0.3146(3) 0.0474(3) 0.0271(6) Uani 1 1 d . . .
C2 C 0.21844(18) 0.2268(3) 0.1386(3) 0.0329(6) Uani 1 1 d . . .
H2 H 0.2491 0.1443 0.1721 0.04 Uiso 1 1 calc R . .
C3 C 0.12278(19) 0.2611(3) 0.1807(3) 0.0404(7) Uani 1 1 d . . .
H3 H 0.0891 0.1991 0.2426 0.049 Uiso 1 1 calc R . .
C4 C 0.1248(2) 0.4614(3) 0.0522(4) 0.0424(7) Uani 1 1 d . . .
H4 H 0.093 0.5443 0.0223 0.051 Uiso 1 1 calc R . .
C5 C 0.2196(2) 0.4352(3) 0.0035(3) 0.0353(6) Uani 1 1 d . . .
H5 H 0.2515 0.4985 -0.059 0.042 Uiso 1 1 calc R . .
C6 C 0.36850(17) 0.2865(3) -0.0145(3) 0.0262(5) Uani 1 1 d . . .
C7 C 0.56342(19) 0.0340(3) 0.2131(3) 0.0305(6) Uani 1 1 d . . .
H7A H 0.5707 0.0917 0.2986 0.046 Uiso 1 1 calc R . .
H7B H 0.6085 -0.0453 0.2195 0.046 Uiso 1 1 calc R . .
H7C H 0.4949 0.0009 0.206 0.046 Uiso 1 1 calc R . .
C8 C 0.58814(18) 0.1180(2) 0.0831(3) 0.0259(5) Uani 1 1 d . . .
C9 C 0.69004(18) 0.1113(2) 0.0213(3) 0.0290(6) Uani 1 1 d . . .
C10 C 0.7086(2) 0.1553(3) -0.1167(3) 0.0346(6) Uani 1 1 d . . .
H10 H 0.6551 0.1854 -0.1752 0.042 Uiso 1 1 calc R . .
C11 C 0.8041(2) 0.1560(3) -0.1708(4) 0.0408(7) Uani 1 1 d . . .
H11 H 0.8156 0.1835 -0.2668 0.049 Uiso 1 1 calc R . .
C12 C 0.8833(2) 0.1163(3) -0.0840(4) 0.0463(8) Uani 1 1 d . . .
H12 H 0.9493 0.1208 -0.1192 0.056 Uiso 1 1 calc R . .
C13 C 0.8659(2) 0.0707(3) 0.0520(4) 0.0451(8) Uani 1 1 d . . .
H13 H 0.9198 0.0415 0.1102 0.054 Uiso 1 1 calc R . .
C14 C 0.7701(2) 0.0667(3) 0.1059(3) 0.0357(6) Uani 1 1 d . . .
H14 H 0.7586 0.0337 0.2 0.043 Uiso 1 1 calc R . .
N1 N 0.43312(15) 0.2132(2) 0.0673(2) 0.0268(5) Uani 1 1 d . . .
N2 N 0.07526(18) 0.3760(3) 0.1394(3) 0.0438(7) Uani 1 1 d . . .
N3 N 0.52849(15) 0.1985(2) 0.0149(2) 0.0274(5) Uani 1 1 d . . .
O1 O 0.38732(14) 0.3280(2) -0.1346(2) 0.0371(5) Uani 1 1 d . . .
H1 H 0.416(2) 0.195(3) 0.163(4) 0.031(8) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   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 1.378(4) . ?
C1 C5 1.397(4) . ?
C1 C6 1.500(3) . ?
C2 C3 1.390(4) . ?
C2 H2 0.95 . ?
C3 N2 1.338(4) . ?
C3 H3 0.95 . ?
C4 N2 1.340(4) . ?
C4 C5 1.383(4) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
C6 O1 1.221(3) . ?
C6 N1 1.358(3) . ?
C7 C8 1.501(4) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 N3 1.287(3) . ?
C8 C9 1.494(3) . ?
C9 C10 1.383(4) . ?
C9 C14 1.404(4) . ?
C10 C11 1.387(4) . ?
C10 H10 0.95 . ?
C11 C12 1.394(5) . ?
C11 H11 0.95 . ?
C12 C13 1.369(5) . ?
C12 H12 0.95 . ?
C13 C14 1.389(4) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
N1 N3 1.386(3) . ?
N1 H1 0.94(3) . ?

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 C5 117.9(2) . . ?
C2 C1 C6 124.7(2) . . ?
C5 C1 C6 117.3(2) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
N2 C3 C2 124.0(3) . . ?
N2 C3 H3 118 . . ?
C2 C3 H3 118 . . ?
N2 C4 C5 123.5(3) . . ?
N2 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C4 C5 C1 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C1 C5 H5 120.4 . . ?
O1 C6 N1 123.8(2) . . ?
O1 C6 C1 119.1(2) . . ?
N1 C6 C1 117.1(2) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 114.1(2) . . ?
N3 C8 C7 126.1(2) . . ?
C9 C8 C7 119.8(2) . . ?
C10 C9 C14 118.7(2) . . ?
C10 C9 C8 121.2(2) . . ?
C14 C9 C8 120.1(2) . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 120.1(3) . . ?
C13 C14 H14 120 . . ?
C9 C14 H14 120 . . ?
C6 N1 N3 116.6(2) . . ?
C6 N1 H1 118.6(18) . . ?
N3 N1 H1 123.0(18) . . ?
C3 N2 C4 116.6(3) . . ?
C8 N3 N1 117.8(2) . . ?

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
C5 C1 C2 C3 0.9(4) . . . . ?
C6 C1 C2 C3 -175.7(2) . . . . ?
C1 C2 C3 N2 -0.8(4) . . . . ?
N2 C4 C5 C1 -0.7(5) . . . . ?
C2 C1 C5 C4 -0.2(4) . . . . ?
C6 C1 C5 C4 176.7(2) . . . . ?
C2 C1 C6 O1 146.4(3) . . . . ?
C5 C1 C6 O1 -30.3(3) . . . . ?
C2 C1 C6 N1 -32.6(4) . . . . ?
C5 C1 C6 N1 150.8(2) . . . . ?
N3 C8 C9 C10 -17.4(3) . . . . ?
C7 C8 C9 C10 162.2(2) . . . . ?
N3 C8 C9 C14 159.2(2) . . . . ?
C7 C8 C9 C14 -21.2(3) . . . . ?
C14 C9 C10 C11 -0.2(4) . . . . ?
C8 C9 C10 C11 176.4(2) . . . . ?
C9 C10 C11 C12 -2.1(4) . . . . ?
C10 C11 C12 C13 3.0(5) . . . . ?
C11 C12 C13 C14 -1.5(5) . . . . ?
C12 C13 C14 C9 -0.8(4) . . . . ?
C10 C9 C14 C13 1.7(4) . . . . ?
C8 C9 C14 C13 -175.0(2) . . . . ?
O1 C6 N1 N3 6.7(4) . . . . ?
C1 C6 N1 N3 -174.3(2) . . . . ?
C2 C3 N2 C4 -0.1(5) . . . . ?
C5 C4 N2 C3 0.8(5) . . . . ?
C9 C8 N3 N1 -178.4(2) . . . . ?
C7 C8 N3 N1 2.0(4) . . . . ?
C6 N1 N3 C8 -173.1(2) . . . . ?

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
N1 H1 O1 0.94(3) 1.95(3) 2.887(3) 175(3) 4_566

####################################################################### 
# 
# 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_11a_dh23_p
_database_code_depnum_ccdc_archive 'CCDC 970534'
_audit_update_record             
;
2013-11-06 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;


_audit_creation_date             2013-11-04T11:03:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O'
_chemical_formula_sum            'C14 H13 N3 O'
_chemical_formula_weight         239.27

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
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                   25.8998(13)
_cell_length_b                   5.5463(3)
_cell_length_c                   8.3187(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.876(4)
_cell_angle_gamma                90
_cell_volume                     1188.69(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4457
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      28.46

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_T_max  0.9948

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_number            14365
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             2866
_reflns_number_gt                2245
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;

#----------------------------------------------------------------------------#
#                   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)+(0.0542P)²+1.5926P] 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_number_reflns         2866
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1587
_refine_ls_wR_factor_gt          0.148
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 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 0.36288(8) 0.0600(4) 0.6621(2) 0.0217(4) Uani 1 1 d . . .
C2 C 0.38840(8) 0.2087(4) 0.7791(2) 0.0256(4) Uani 1 1 d . . .
H2 H 0.3734 0.3574 0.8068 0.031 Uiso 1 1 calc R . .
C3 C 0.43613(8) 0.1365(4) 0.8547(3) 0.0299(5) Uani 1 1 d . . .
H3 H 0.4531 0.2399 0.9345 0.036 Uiso 1 1 calc R . .
C4 C 0.43498(8) -0.2105(4) 0.7083(3) 0.0301(5) Uani 1 1 d . . .
H4 H 0.4511 -0.3572 0.6822 0.036 Uiso 1 1 calc R . .
C5 C 0.38723(8) -0.1544(4) 0.6267(3) 0.0273(4) Uani 1 1 d . . .
H5 H 0.3712 -0.2612 0.5473 0.033 Uiso 1 1 calc R . .
C6 C 0.31228(8) 0.1171(4) 0.5649(2) 0.0226(4) Uani 1 1 d . . .
C7 C 0.22413(9) 0.7060(4) 0.6734(3) 0.0291(5) Uani 1 1 d . . .
H7A H 0.2095 0.6931 0.7771 0.044 Uiso 1 1 calc R . .
H7B H 0.2128 0.8577 0.6206 0.044 Uiso 1 1 calc R . .
H7C H 0.2621 0.7031 0.692 0.044 Uiso 1 1 calc R . .
C8 C 0.20579(8) 0.4989(4) 0.5677(2) 0.0227(4) Uani 1 1 d . . .
C9 C 0.15173(8) 0.5010(4) 0.4861(2) 0.0224(4) Uani 1 1 d . . .
C10 C 0.13487(8) 0.3243(4) 0.3733(3) 0.0286(5) Uani 1 1 d . . .
H10 H 0.1584 0.2026 0.3466 0.034 Uiso 1 1 calc R . .
C11 C 0.08460(9) 0.3236(4) 0.3000(3) 0.0332(5) Uani 1 1 d . . .
H11 H 0.0739 0.2024 0.223 0.04 Uiso 1 1 calc R . .
C12 C 0.04961(8) 0.4989(4) 0.3380(3) 0.0335(5) Uani 1 1 d . . .
H12 H 0.0149 0.4975 0.2882 0.04 Uiso 1 1 calc R . .
C13 C 0.06575(9) 0.6750(4) 0.4488(3) 0.0354(5) Uani 1 1 d . . .
H13 H 0.042 0.7954 0.4756 0.042 Uiso 1 1 calc R . .
C14 C 0.11636(9) 0.6782(4) 0.5216(3) 0.0299(5) Uani 1 1 d . . .
H14 H 0.1271 0.8023 0.5965 0.036 Uiso 1 1 calc R . .
N1 N 0.28151(7) 0.2869(3) 0.6218(2) 0.0248(4) Uani 1 1 d . . .
H1 H 0.2888(10) 0.355(5) 0.720(3) 0.038(7) Uiso 1 1 d . . .
N2 N 0.45971(7) -0.0697(4) 0.8221(2) 0.0307(4) Uani 1 1 d . . .
N3 N 0.23221(7) 0.3097(3) 0.5398(2) 0.0256(4) Uani 1 1 d . . .
O1 O 0.30068(6) 0.0101(3) 0.43636(16) 0.0274(4) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   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 1.390(3) . ?
C1 C5 1.392(3) . ?
C1 C6 1.502(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.95 . ?
C3 N2 1.337(3) . ?
C3 H3 0.95 . ?
C4 N2 1.339(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
C6 O1 1.233(2) . ?
C6 N1 1.351(3) . ?
C7 C8 1.494(3) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 N3 1.287(3) . ?
C8 C9 1.492(3) . ?
C9 C10 1.396(3) . ?
C9 C14 1.396(3) . ?
C10 C11 1.380(3) . ?
C10 H10 0.95 . ?
C11 C12 1.387(3) . ?
C11 H11 0.95 . ?
C12 C13 1.378(3) . ?
C12 H12 0.95 . ?
C13 C14 1.387(3) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
N1 N3 1.390(2) . ?
N1 H1 0.90(3) . ?

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 C5 117.52(19) . . ?
C2 C1 C6 125.32(18) . . ?
C5 C1 C6 117.09(18) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
N2 C3 C2 124.0(2) . . ?
N2 C3 H3 118 . . ?
C2 C3 H3 118 . . ?
N2 C4 C5 123.7(2) . . ?
N2 C4 H4 118.2 . . ?
C5 C4 H4 118.2 . . ?
C4 C5 C1 119.3(2) . . ?
C4 C5 H5 120.3 . . ?
C1 C5 H5 120.3 . . ?
O1 C6 N1 122.66(18) . . ?
O1 C6 C1 119.18(18) . . ?
N1 C6 C1 118.15(17) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 114.58(18) . . ?
N3 C8 C7 126.15(19) . . ?
C9 C8 C7 119.26(17) . . ?
C10 C9 C14 118.04(19) . . ?
C10 C9 C8 120.98(18) . . ?
C14 C9 C8 120.98(18) . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 120.7(2) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C6 N1 N3 115.89(16) . . ?
C6 N1 H1 122.2(17) . . ?
N3 N1 H1 120.2(17) . . ?
C3 N2 C4 116.55(19) . . ?
C8 N3 N1 117.68(17) . . ?

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
C5 C1 C2 C3 -0.4(3) . . . . ?
C6 C1 C2 C3 -177.32(18) . . . . ?
C1 C2 C3 N2 0.1(3) . . . . ?
N2 C4 C5 C1 0.4(3) . . . . ?
C2 C1 C5 C4 0.2(3) . . . . ?
C6 C1 C5 C4 177.38(18) . . . . ?
C2 C1 C6 O1 159.45(19) . . . . ?
C5 C1 C6 O1 -17.5(3) . . . . ?
C2 C1 C6 N1 -19.8(3) . . . . ?
C5 C1 C6 N1 163.28(18) . . . . ?
N3 C8 C9 C10 -7.8(3) . . . . ?
C7 C8 C9 C10 173.17(19) . . . . ?
N3 C8 C9 C14 171.48(19) . . . . ?
C7 C8 C9 C14 -7.5(3) . . . . ?
C14 C9 C10 C11 -0.5(3) . . . . ?
C8 C9 C10 C11 178.81(19) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C9 -1.0(3) . . . . ?
C10 C9 C14 C13 1.2(3) . . . . ?
C8 C9 C14 C13 -178.11(19) . . . . ?
O1 C6 N1 N3 9.3(3) . . . . ?
C1 C6 N1 N3 -171.45(16) . . . . ?
C2 C3 N2 C4 0.4(3) . . . . ?
C5 C4 N2 C3 -0.7(3) . . . . ?
C9 C8 N3 N1 -175.13(16) . . . . ?
C7 C8 N3 N1 3.8(3) . . . . ?
C6 N1 N3 C8 -165.98(18) . . . . ?

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
N1 H1 O1 0.90(3) 1.95(3) 2.845(2) 176(2) 4_566

####################################################################### 
# 
# 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_11a_dh40_p
_database_code_depnum_ccdc_archive 'CCDC 970535'
_audit_update_record             
;
2013-11-06 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;


_audit_creation_date             2013-11-04T10:52:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O'
_chemical_formula_sum            'C14 H13 N3 O'
_chemical_formula_weight         239.27

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
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                   10.2114(2)
_cell_length_b                   30.3315(7)
_cell_length_c                   8.2353(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.1930(10)
_cell_angle_gamma                90
_cell_volume                     2393.92(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8575
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.23

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.138
0 -1 0 0.105
-1 0 0 0.051
1 0 0 0.035
-1 0 2 0.274
1 0 -2 0.2

_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_T_max  0.9914

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_number            35411
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             5778
_reflns_number_gt                4579
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;

#----------------------------------------------------------------------------#
#                   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)+(0.0537P)²+0.5727P] 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_number_reflns         5778
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 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
C1A C 0.23621(12) 0.28524(4) -0.06611(14) 0.0239(2) Uani 1 1 d . . .
C2A C 0.15897(13) 0.25398(4) -0.18313(16) 0.0288(3) Uani 1 1 d . . .
H2A H 0.1824 0.2236 -0.1669 0.035 Uiso 1 1 calc R . .
C3A C 0.04680(13) 0.26801(5) -0.32443(16) 0.0332(3) Uani 1 1 d . . .
H3A H -0.0057 0.2464 -0.4037 0.04 Uiso 1 1 calc R . .
C4A C 0.08232(14) 0.33945(5) -0.23945(19) 0.0382(3) Uani 1 1 d . . .
H4A H 0.0559 0.3696 -0.2583 0.046 Uiso 1 1 calc R . .
C5A C 0.19493(13) 0.32891(4) -0.09346(17) 0.0303(3) Uani 1 1 d . . .
H5A H 0.2428 0.3511 -0.0138 0.036 Uiso 1 1 calc R . .
C6A C 0.35596(12) 0.27380(4) 0.09463(14) 0.0240(2) Uani 1 1 d . . .
C7A C 0.62339(12) 0.19566(4) 0.22629(14) 0.0240(2) Uani 1 1 d . . .
C8A C 0.72129(12) 0.18041(4) 0.39731(14) 0.0238(2) Uani 1 1 d . . .
C9A C 0.72012(13) 0.19985(4) 0.55060(16) 0.0301(3) Uani 1 1 d . . .
H9A H 0.6548 0.2226 0.5458 0.036 Uiso 1 1 calc R . .
C10A C 0.81282(14) 0.18646(4) 0.70955(16) 0.0319(3) Uani 1 1 d . . .
H10A H 0.811 0.2001 0.8126 0.038 Uiso 1 1 calc R . .
C11A C 0.90783(14) 0.15332(4) 0.71878(16) 0.0322(3) Uani 1 1 d . . .
H11A H 0.9724 0.1445 0.8277 0.039 Uiso 1 1 calc R . .
C12A C 0.90850(15) 0.13313(5) 0.56930(17) 0.0373(3) Uani 1 1 d . . .
H12A H 0.9726 0.11 0.5754 0.045 Uiso 1 1 calc R . .
C13A C 0.81557(14) 0.14653(4) 0.40926(16) 0.0329(3) Uani 1 1 d . . .
H13A H 0.8167 0.1323 0.307 0.04 Uiso 1 1 calc R . .
C14A C 0.64039(13) 0.17754(5) 0.06530(15) 0.0318(3) Uani 1 1 d . . .
H14A H 0.6065 0.1471 0.0478 0.048 Uiso 1 1 calc R . .
H14B H 0.7392 0.1782 0.0772 0.048 Uiso 1 1 calc R . .
H14C H 0.5865 0.1955 -0.0343 0.048 Uiso 1 1 calc R . .
N1A N 0.43246(10) 0.23836(3) 0.08279(13) 0.0249(2) Uani 1 1 d . . .
N2A N 0.00851(11) 0.31000(4) -0.35537(15) 0.0378(3) Uani 1 1 d . . .
N3A N 0.53170(10) 0.22377(3) 0.23521(12) 0.0250(2) Uani 1 1 d . . .
O1A O 0.37763(9) 0.29570(3) 0.22657(11) 0.0319(2) Uani 1 1 d . . .
H1A H 0.4239(16) 0.2282(5) -0.024(2) 0.039(4) Uiso 1 1 d . . .
C1B C 0.94050(12) -0.03728(4) 0.74723(15) 0.0253(2) Uani 1 1 d . . .
C2B C 1.08165(13) -0.04227(4) 0.77310(17) 0.0307(3) Uani 1 1 d . . .
H2B H 1.1157 -0.0389 0.68 0.037 Uiso 1 1 calc R . .
C3B C 1.17139(13) -0.05230(4) 0.93829(17) 0.0322(3) Uani 1 1 d . . .
H3B H 1.268 -0.0552 0.956 0.039 Uiso 1 1 calc R . .
C4B C 0.99303(13) -0.05519(4) 1.04482(16) 0.0272(3) Uani 1 1 d . . .
H4B H 0.961 -0.0606 1.1384 0.033 Uiso 1 1 calc R . .
C5B C 0.89532(12) -0.04469(4) 0.88525(15) 0.0252(2) Uani 1 1 d . . .
H5B H 0.7991 -0.0426 0.8708 0.03 Uiso 1 1 calc R . .
C6B C 0.84132(13) -0.02454(4) 0.57148(15) 0.0294(3) Uani 1 1 d . . .
C7B C 0.57744(12) 0.05552(4) 0.42801(15) 0.0248(2) Uani 1 1 d . . .
C8B C 0.48494(12) 0.07253(4) 0.25719(15) 0.0244(2) Uani 1 1 d . . .
C9B C 0.46347(13) 0.04802(5) 0.10669(15) 0.0304(3) Uani 1 1 d . . .
H9B H 0.5075 0.0201 0.1142 0.037 Uiso 1 1 calc R . .
C10B C 0.37904(14) 0.06363(5) -0.05349(16) 0.0347(3) Uani 1 1 d . . .
H10B H 0.3649 0.0464 -0.1544 0.042 Uiso 1 1 calc R . .
C11B C 0.31543(13) 0.10440(5) -0.06621(17) 0.0331(3) Uani 1 1 d . . .
H11B H 0.2591 0.1155 -0.176 0.04 Uiso 1 1 calc R . .
C12B C 0.33436(13) 0.12882(4) 0.08154(17) 0.0323(3) Uani 1 1 d . . .
H12B H 0.2896 0.1566 0.0732 0.039 Uiso 1 1 calc R . .
C13B C 0.41835(12) 0.11318(4) 0.24253(16) 0.0274(3) Uani 1 1 d . . .
H13B H 0.4304 0.1303 0.3432 0.033 Uiso 1 1 calc R . .
C14B C 0.56583(14) 0.07410(5) 0.59112(16) 0.0369(3) Uani 1 1 d . . .
H14D H 0.5833 0.0507 0.6782 0.055 Uiso 1 1 calc R . .
H14E H 0.4719 0.0861 0.5671 0.055 Uiso 1 1 calc R . .
H14F H 0.6348 0.0977 0.6347 0.055 Uiso 1 1 calc R . .
N1B N 0.75379(11) 0.00896(4) 0.57594(13) 0.0276(2) Uani 1 1 d . . .
N2B N 1.12985(11) -0.05810(3) 1.07424(14) 0.0304(2) Uani 1 1 d . . .
N3B N 0.66235(10) 0.02495(3) 0.42009(12) 0.0266(2) Uani 1 1 d . . .
O1B O 0.84237(12) -0.04305(4) 0.44090(12) 0.0470(3) Uani 1 1 d . . .
H1B H 0.7717(16) 0.0236(5) 0.672(2) 0.039(4) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   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
C1A C5A 1.3848(17) . ?
C1A C2A 1.3874(17) . ?
C1A C6A 1.5002(15) . ?
C2A C3A 1.3881(16) . ?
C2A H2A 0.95 . ?
C3A N2A 1.3308(19) . ?
C3A H3A 0.95 . ?
C4A N2A 1.3343(19) . ?
C4A C5A 1.3840(18) . ?
C4A H4A 0.95 . ?
C5A H5A 0.95 . ?
C6A O1A 1.2268(14) . ?
C6A N1A 1.3519(16) . ?
C7A N3A 1.2871(16) . ?
C7A C8A 1.4916(15) . ?
C7A C14A 1.4996(17) . ?
C8A C13A 1.3882(17) . ?
C8A C9A 1.3971(17) . ?
C9A C10A 1.3853(16) . ?
C9A H9A 0.95 . ?
C10A C11A 1.3807(19) . ?
C10A H10A 0.95 . ?
C11A C12A 1.3771(19) . ?
C11A H11A 0.95 . ?
C12A C13A 1.3927(17) . ?
C12A H12A 0.95 . ?
C13A H13A 0.95 . ?
C14A H14A 0.98 . ?
C14A H14B 0.98 . ?
C14A H14C 0.98 . ?
N1A N3A 1.3857(13) . ?
N1A H1A 0.907(17) . ?
C1B C5B 1.3847(17) . ?
C1B C2B 1.3906(17) . ?
C1B C6B 1.5027(16) . ?
C2B C3B 1.3864(17) . ?
C2B H2B 0.95 . ?
C3B N2B 1.3387(18) . ?
C3B H3B 0.95 . ?
C4B N2B 1.3360(17) . ?
C4B C5B 1.3850(16) . ?
C4B H4B 0.95 . ?
C5B H5B 0.95 . ?
C6B O1B 1.2165(15) . ?
C6B N1B 1.3619(16) . ?
C7B N3B 1.2864(15) . ?
C7B C8B 1.4900(15) . ?
C7B C14B 1.4987(17) . ?
C8B C13B 1.3930(17) . ?
C8B C9B 1.3962(17) . ?
C9B C10B 1.3865(17) . ?
C9B H9B 0.95 . ?
C10B C11B 1.3838(19) . ?
C10B H10B 0.95 . ?
C11B C12B 1.380(2) . ?
C11B H11B 0.95 . ?
C12B C13B 1.3905(17) . ?
C12B H12B 0.95 . ?
C13B H13B 0.95 . ?
C14B H14D 0.98 . ?
C14B H14E 0.98 . ?
C14B H14F 0.98 . ?
N1B N3B 1.3882(13) . ?
N1B H1B 0.873(16) . ?

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
C5A C1A C2A 118.20(11) . . ?
C5A C1A C6A 118.32(11) . . ?
C2A C1A C6A 123.34(11) . . ?
C1A C2A C3A 118.65(12) . . ?
C1A C2A H2A 120.7 . . ?
C3A C2A H2A 120.7 . . ?
N2A C3A C2A 123.83(13) . . ?
N2A C3A H3A 118.1 . . ?
C2A C3A H3A 118.1 . . ?
N2A C4A C5A 124.17(13) . . ?
N2A C4A H4A 117.9 . . ?
C5A C4A H4A 117.9 . . ?
C4A C5A C1A 118.50(12) . . ?
C4A C5A H5A 120.8 . . ?
C1A C5A H5A 120.8 . . ?
O1A C6A N1A 124.22(10) . . ?
O1A C6A C1A 119.94(11) . . ?
N1A C6A C1A 115.82(10) . . ?
N3A C7A C8A 114.53(10) . . ?
N3A C7A C14A 127.00(10) . . ?
C8A C7A C14A 118.47(10) . . ?
C13A C8A C9A 118.05(11) . . ?
C13A C8A C7A 121.25(11) . . ?
C9A C8A C7A 120.69(11) . . ?
C10A C9A C8A 120.93(12) . . ?
C10A C9A H9A 119.5 . . ?
C8A C9A H9A 119.5 . . ?
C11A C10A C9A 120.22(12) . . ?
C11A C10A H10A 119.9 . . ?
C9A C10A H10A 119.9 . . ?
C12A C11A C10A 119.66(11) . . ?
C12A C11A H11A 120.2 . . ?
C10A C11A H11A 120.2 . . ?
C11A C12A C13A 120.27(12) . . ?
C11A C12A H12A 119.9 . . ?
C13A C12A H12A 119.9 . . ?
C8A C13A C12A 120.83(12) . . ?
C8A C13A H13A 119.6 . . ?
C12A C13A H13A 119.6 . . ?
C7A C14A H14A 109.5 . . ?
C7A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C7A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C6A N1A N3A 116.66(10) . . ?
C6A N1A H1A 118.3(10) . . ?
N3A N1A H1A 124.5(10) . . ?
C3A N2A C4A 116.59(11) . . ?
C7A N3A N1A 118.61(10) . . ?
C5B C1B C2B 118.56(11) . . ?
C5B C1B C6B 121.85(11) . . ?
C2B C1B C6B 119.59(11) . . ?
C3B C2B C1B 118.24(12) . . ?
C3B C2B H2B 120.9 . . ?
C1B C2B H2B 120.9 . . ?
N2B C3B C2B 123.82(12) . . ?
N2B C3B H3B 118.1 . . ?
C2B C3B H3B 118.1 . . ?
N2B C4B C5B 123.57(12) . . ?
N2B C4B H4B 118.2 . . ?
C5B C4B H4B 118.2 . . ?
C1B C5B C4B 118.76(11) . . ?
C1B C5B H5B 120.6 . . ?
C4B C5B H5B 120.6 . . ?
O1B C6B N1B 125.05(11) . . ?
O1B C6B C1B 121.60(11) . . ?
N1B C6B C1B 113.35(10) . . ?
N3B C7B C8B 114.87(10) . . ?
N3B C7B C14B 125.44(11) . . ?
C8B C7B C14B 119.70(10) . . ?
C13B C8B C9B 118.17(11) . . ?
C13B C8B C7B 121.32(11) . . ?
C9B C8B C7B 120.52(11) . . ?
C10B C9B C8B 121.21(12) . . ?
C10B C9B H9B 119.4 . . ?
C8B C9B H9B 119.4 . . ?
C11B C10B C9B 119.91(12) . . ?
C11B C10B H10B 120 . . ?
C9B C10B H10B 120 . . ?
C12B C11B C10B 119.59(11) . . ?
C12B C11B H11B 120.2 . . ?
C10B C11B H11B 120.2 . . ?
C11B C12B C13B 120.67(12) . . ?
C11B C12B H12B 119.7 . . ?
C13B C12B H12B 119.7 . . ?
C12B C13B C8B 120.44(12) . . ?
C12B C13B H13B 119.8 . . ?
C8B C13B H13B 119.8 . . ?
C7B C14B H14D 109.5 . . ?
C7B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C7B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C6B N1B N3B 118.29(10) . . ?
C6B N1B H1B 118.1(10) . . ?
N3B N1B H1B 121.7(10) . . ?
C4B N2B C3B 116.94(10) . . ?
C7B N3B N1B 117.07(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
C5A C1A C2A C3A 1.86(18) . . . . ?
C6A C1A C2A C3A 177.57(12) . . . . ?
C1A C2A C3A N2A 0.2(2) . . . . ?
N2A C4A C5A C1A 1.2(2) . . . . ?
C2A C1A C5A C4A -2.51(18) . . . . ?
C6A C1A C5A C4A -178.44(12) . . . . ?
C5A C1A C6A O1A 30.22(17) . . . . ?
C2A C1A C6A O1A -145.47(13) . . . . ?
C5A C1A C6A N1A -151.03(11) . . . . ?
C2A C1A C6A N1A 33.28(17) . . . . ?
N3A C7A C8A C13A 172.63(12) . . . . ?
C14A C7A C8A C13A -7.49(18) . . . . ?
N3A C7A C8A C9A -7.10(17) . . . . ?
C14A C7A C8A C9A 172.78(12) . . . . ?
C13A C8A C9A C10A 1.65(19) . . . . ?
C7A C8A C9A C10A -178.61(12) . . . . ?
C8A C9A C10A C11A -0.4(2) . . . . ?
C9A C10A C11A C12A -1.1(2) . . . . ?
C10A C11A C12A C13A 1.1(2) . . . . ?
C9A C8A C13A C12A -1.6(2) . . . . ?
C7A C8A C13A C12A 178.69(12) . . . . ?
C11A C12A C13A C8A 0.2(2) . . . . ?
O1A C6A N1A N3A 6.89(18) . . . . ?
C1A C6A N1A N3A -171.80(10) . . . . ?
C2A C3A N2A C4A -1.6(2) . . . . ?
C5A C4A N2A C3A 0.8(2) . . . . ?
C8A C7A N3A N1A -177.25(10) . . . . ?
C14A C7A N3A N1A 2.88(18) . . . . ?
C6A N1A N3A C7A -167.44(11) . . . . ?
C5B C1B C2B C3B -3.16(18) . . . . ?
C6B C1B C2B C3B 177.43(11) . . . . ?
C1B C2B C3B N2B 1.0(2) . . . . ?
C2B C1B C5B C4B 2.32(17) . . . . ?
C6B C1B C5B C4B -178.29(11) . . . . ?
N2B C4B C5B C1B 0.84(18) . . . . ?
C5B C1B C6B O1B -131.70(14) . . . . ?
C2B C1B C6B O1B 47.70(19) . . . . ?
C5B C1B C6B N1B 48.39(16) . . . . ?
C2B C1B C6B N1B -132.22(13) . . . . ?
N3B C7B C8B C13B -160.90(11) . . . . ?
C14B C7B C8B C13B 19.39(18) . . . . ?
N3B C7B C8B C9B 18.71(17) . . . . ?
C14B C7B C8B C9B -161.00(12) . . . . ?
C13B C8B C9B C10B 0.40(19) . . . . ?
C7B C8B C9B C10B -179.22(12) . . . . ?
C8B C9B C10B C11B 0.6(2) . . . . ?
C9B C10B C11B C12B -1.3(2) . . . . ?
C10B C11B C12B C13B 1.0(2) . . . . ?
C11B C12B C13B C8B 0.06(19) . . . . ?
C9B C8B C13B C12B -0.75(18) . . . . ?
C7B C8B C13B C12B 178.87(11) . . . . ?
O1B C6B N1B N3B -3.1(2) . . . . ?
C1B C6B N1B N3B 176.80(10) . . . . ?
C5B C4B N2B C3B -2.99(18) . . . . ?
C2B C3B N2B C4B 2.04(19) . . . . ?
C8B C7B N3B N1B 178.05(10) . . . . ?
C14B C7B N3B N1B -2.26(19) . . . . ?
C6B N1B N3B C7B 177.63(11) . . . . ?

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
N1A H1A O1A 0.907(17) 2.074(17) 2.9754(14) 172.8(14) 4_565
N1B H1B N2B 0.873(16) 2.238(17) 3.0935(15) 166.4(14) 3_757

####################################################################### 
# 
# 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_13d_soln_needles_p
_database_code_depnum_ccdc_archive 'CCDC 970536'
_audit_update_record             
;
2013-11-06 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;


_audit_creation_date             2013-11-04T10:38:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O'
_chemical_formula_sum            'C14 H13 N3 O'
_chemical_formula_weight         239.27

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_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                   6.3542(4)
_cell_length_b                   7.6624(6)
_cell_length_c                   49.231(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2397.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6480
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      27.68

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

_exptl_crystal_description       needles
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.046
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.996

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
        Bruker D8 Venture Photon CCD area detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_number            12081
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_reflns_number_total             2124
_reflns_number_gt                1777
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX3 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;

#----------------------------------------------------------------------------#
#                   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)+(0.0629P)²+0.9134P] 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_number_reflns         2124
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.113
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_restrained_S_all      1.194
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.075

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 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 0.6131(3) 0.4903(2) 0.06730(3) 0.0229(4) Uani 1 1 d . . .
C2 C 0.7812(3) 0.5335(3) 0.05093(4) 0.0272(5) Uani 1 1 d . . .
H2 H 0.9203 0.5011 0.0559 0.033 Uiso 1 1 calc R . .
C3 C 0.7441(3) 0.6248(3) 0.02714(4) 0.0323(5) Uani 1 1 d . . .
H3 H 0.8611 0.6524 0.0159 0.039 Uiso 1 1 calc R . .
C4 C 0.3948(3) 0.6344(3) 0.03517(4) 0.0397(6) Uani 1 1 d . . .
H4 H 0.2578 0.6705 0.0299 0.048 Uiso 1 1 calc R . .
C5 C 0.4150(3) 0.5417(3) 0.05915(4) 0.0356(5) Uani 1 1 d . . .
H5 H 0.2948 0.514 0.0698 0.043 Uiso 1 1 calc R . .
C6 C 0.6365(3) 0.3815(2) 0.09240(3) 0.0222(4) Uani 1 1 d . . .
C7 C 1.1690(3) 0.4793(3) 0.13692(4) 0.0342(5) Uani 1 1 d . . .
H7A H 1.1852 0.4653 0.1172 0.051 Uiso 1 1 calc R . .
H7B H 1.2989 0.4431 0.146 0.051 Uiso 1 1 calc R . .
H7C H 1.1401 0.602 0.1411 0.051 Uiso 1 1 calc R . .
C8 C 0.9904(3) 0.3690(2) 0.14661(3) 0.0237(4) Uani 1 1 d . . .
C9 C 0.9981(3) 0.2916(2) 0.17429(4) 0.0238(4) Uani 1 1 d . . .
C10 C 0.8575(3) 0.1630(3) 0.18210(4) 0.0305(5) Uani 1 1 d . . .
H10 H 0.7574 0.1206 0.1694 0.037 Uiso 1 1 calc R . .
C11 C 0.8605(3) 0.0950(3) 0.20819(4) 0.0340(5) Uani 1 1 d . . .
H11 H 0.7641 0.0058 0.2131 0.041 Uiso 1 1 calc R . .
C12 C 1.0031(3) 0.1568(3) 0.22695(4) 0.0309(5) Uani 1 1 d . . .
H12 H 1.0048 0.1107 0.2449 0.037 Uiso 1 1 calc R . .
C13 C 1.1425(3) 0.2852(3) 0.21969(4) 0.0327(5) Uani 1 1 d . . .
H13 H 1.24 0.3288 0.2326 0.039 Uiso 1 1 calc R . .
C14 C 1.1417(3) 0.3517(3) 0.19345(4) 0.0304(5) Uani 1 1 d . . .
H14 H 1.2403 0.4393 0.1885 0.036 Uiso 1 1 calc R . .
N1 N 0.8026(2) 0.4218(2) 0.10827(3) 0.0251(4) Uani 1 1 d . . .
N2 N 0.5551(3) 0.6759(2) 0.01913(3) 0.0344(5) Uani 1 1 d . . .
N3 N 0.8220(2) 0.3373(2) 0.13301(3) 0.0258(4) Uani 1 1 d . . .
O1 O 0.5135(2) 0.26217(17) 0.09703(3) 0.0286(4) Uani 1 1 d . . .
H1 H 0.875(3) 0.520(3) 0.1061(4) 0.037(6) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   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 1.378(3) . ?
C1 C5 1.378(3) . ?
C1 C6 1.498(2) . ?
C2 C3 1.385(3) . ?
C2 H2 0.95 . ?
C3 N2 1.323(3) . ?
C3 H3 0.95 . ?
C4 N2 1.328(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
C6 O1 1.224(2) . ?
C6 N1 1.349(2) . ?
C7 C8 1.494(3) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 N3 1.285(2) . ?
C8 C9 1.487(2) . ?
C9 C10 1.384(3) . ?
C9 C14 1.391(3) . ?
C10 C11 1.386(3) . ?
C10 H10 0.95 . ?
C11 C12 1.378(3) . ?
C11 H11 0.95 . ?
C12 C13 1.371(3) . ?
C12 H12 0.95 . ?
C13 C14 1.388(3) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
N1 N3 1.385(2) . ?
N1 H1 0.89(2) . ?

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 C5 117.96(17) . . ?
C2 C1 C6 122.61(16) . . ?
C5 C1 C6 119.32(16) . . ?
C1 C2 C3 118.96(18) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
N2 C3 C2 123.77(18) . . ?
N2 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
N2 C4 C5 124.00(19) . . ?
N2 C4 H4 118 . . ?
C5 C4 H4 118 . . ?
C1 C5 C4 118.66(18) . . ?
C1 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
O1 C6 N1 124.24(16) . . ?
O1 C6 C1 120.39(16) . . ?
N1 C6 C1 115.33(16) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 115.45(16) . . ?
N3 C8 C7 124.94(16) . . ?
C9 C8 C7 119.58(16) . . ?
C10 C9 C14 118.09(17) . . ?
C10 C9 C8 121.14(16) . . ?
C14 C9 C8 120.72(17) . . ?
C9 C10 C11 121.05(18) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 120.08(19) . . ?
C12 C11 H11 120 . . ?
C10 C11 H11 120 . . ?
C13 C12 C11 119.76(18) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.25(18) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.76(19) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C6 N1 N3 118.17(16) . . ?
C6 N1 H1 121.8(14) . . ?
N3 N1 H1 117.2(14) . . ?
C3 N2 C4 116.64(16) . . ?
C8 N3 N1 116.38(16) . . ?

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
C5 C1 C2 C3 -0.4(3) . . . . ?
C6 C1 C2 C3 175.78(17) . . . . ?
C1 C2 C3 N2 0.8(3) . . . . ?
C2 C1 C5 C4 -0.4(3) . . . . ?
C6 C1 C5 C4 -176.66(18) . . . . ?
N2 C4 C5 C1 0.8(4) . . . . ?
C2 C1 C6 O1 -134.62(19) . . . . ?
C5 C1 C6 O1 41.5(3) . . . . ?
C2 C1 C6 N1 43.4(2) . . . . ?
C5 C1 C6 N1 -140.50(19) . . . . ?
N3 C8 C9 C10 14.3(3) . . . . ?
C7 C8 C9 C10 -167.49(18) . . . . ?
N3 C8 C9 C14 -163.03(18) . . . . ?
C7 C8 C9 C14 15.2(3) . . . . ?
C14 C9 C10 C11 -0.5(3) . . . . ?
C8 C9 C10 C11 -177.87(18) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 C9 1.0(3) . . . . ?
C10 C9 C14 C13 -0.4(3) . . . . ?
C8 C9 C14 C13 176.98(18) . . . . ?
O1 C6 N1 N3 -8.1(3) . . . . ?
C1 C6 N1 N3 174.03(15) . . . . ?
C2 C3 N2 C4 -0.4(3) . . . . ?
C5 C4 N2 C3 -0.5(3) . . . . ?
C9 C8 N3 N1 173.98(15) . . . . ?
C7 C8 N3 N1 -4.1(3) . . . . ?
C6 N1 N3 C8 174.80(16) . . . . ?

####################################################################### 
# 
# 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_13d_sublimed_plate_p
_database_code_depnum_ccdc_archive 'CCDC 970537'
_audit_update_record             
;
2013-11-06 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;


_audit_creation_date             2013-11-04T14:08:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O'
_chemical_formula_sum            'C14 H13 N3 O'
_chemical_formula_weight         239.27

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7360(6)
_cell_length_b                   9.8752(6)
_cell_length_c                   26.1543(16)
_cell_angle_alpha                92.856(4)
_cell_angle_beta                 100.295(4)
_cell_angle_gamma                91.291(4)
_cell_volume                     2469.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2417
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      21.29

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

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_special_details           ?

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

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.076
_diffrn_reflns_number            39845
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             9177
_reflns_number_gt                4183
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   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)+(0.0622P)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_number_reflns         9177
_refine_ls_number_parameters     669
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1473
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.16
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 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
H1C H 0.653(4) 0.513(3) 0.0423(13) 0.106(13) Uiso 1 1 d . . .
C1A C 0.1649(3) 0.3060(3) 0.43124(10) 0.0378(7) Uani 1 1 d . . .
C2A C 0.1385(3) 0.3238(3) 0.37851(11) 0.0445(7) Uani 1 1 d . . .
H2A H 0.1302 0.2479 0.3543 0.053 Uiso 1 1 calc R . .
C3A C 0.1244(3) 0.4527(3) 0.36148(12) 0.0514(8) Uani 1 1 d . . .
H3A H 0.1106 0.4632 0.325 0.062 Uiso 1 1 calc R . .
C4A C 0.1527(4) 0.5451(3) 0.44292(13) 0.0622(9) Uani 1 1 d . . .
H4A H 0.1563 0.6229 0.4661 0.075 Uiso 1 1 calc R . .
C5A C 0.1727(3) 0.4206(3) 0.46434(11) 0.0486(8) Uani 1 1 d . . .
H5A H 0.1915 0.4138 0.501 0.058 Uiso 1 1 calc R . .
C6A C 0.1935(3) 0.1743(3) 0.45592(11) 0.0407(7) Uani 1 1 d . . .
C8A C -0.0837(3) -0.0363(3) 0.38917(10) 0.0387(7) Uani 1 1 d . . .
C9A C -0.1952(3) -0.0331(3) 0.34282(11) 0.0414(7) Uani 1 1 d . . .
C10A C -0.2026(3) 0.0745(3) 0.31024(12) 0.0598(9) Uani 1 1 d . . .
H10A H -0.1378 0.1491 0.3186 0.072 Uiso 1 1 calc R . .
C11A C -0.3038(4) 0.0735(4) 0.26573(14) 0.0764(11) Uani 1 1 d . . .
H11A H -0.3087 0.1483 0.244 0.092 Uiso 1 1 calc R . .
C12A C -0.3968(4) -0.0339(4) 0.25261(14) 0.0783(11) Uani 1 1 d . . .
H12A H -0.4648 -0.0346 0.2216 0.094 Uiso 1 1 calc R . .
C13A C -0.3913(4) -0.1391(4) 0.28408(14) 0.0688(10) Uani 1 1 d . . .
H13A H -0.4566 -0.2132 0.2754 0.083 Uiso 1 1 calc R . .
C14A C -0.2910(3) -0.1394(3) 0.32877(12) 0.0558(8) Uani 1 1 d . . .
H14A H -0.288 -0.2145 0.3503 0.067 Uiso 1 1 calc R . .
C7A C -0.0701(3) -0.1611(3) 0.41963(12) 0.0613(9) Uani 1 1 d . . .
H7A1 H -0.0173 -0.2282 0.4029 0.092 Uiso 1 1 calc R . .
H7A2 H -0.1632 -0.1991 0.4208 0.092 Uiso 1 1 calc R . .
H7A3 H -0.0207 -0.1377 0.4551 0.092 Uiso 1 1 calc R . .
N1A N 0.1094(2) 0.0653(2) 0.44025(9) 0.0442(6) Uani 1 1 d . . .
N2A N 0.1287(3) 0.5636(2) 0.39246(11) 0.0579(7) Uani 1 1 d . . .
N3A N -0.0020(2) 0.0693(2) 0.39946(9) 0.0417(6) Uani 1 1 d . . .
O1A O 0.2950(2) 0.16867(18) 0.49166(8) 0.0531(5) Uani 1 1 d . . .
H1A H 0.133(3) -0.011(3) 0.4598(10) 0.055(9) Uiso 1 1 d . . .
C1B C 0.3322(3) -0.2890(3) 0.56984(10) 0.0385(7) Uani 1 1 d . . .
C2B C 0.4541(3) -0.3573(3) 0.56777(13) 0.0555(9) Uani 1 1 d . . .
H2B H 0.5272 -0.3178 0.5532 0.067 Uiso 1 1 calc R . .
C3B C 0.4662(3) -0.4837(3) 0.58741(14) 0.0667(10) Uani 1 1 d . . .
H3B H 0.5498 -0.5301 0.5855 0.08 Uiso 1 1 calc R . .
C4B C 0.2565(4) -0.4774(3) 0.61087(11) 0.0548(8) Uani 1 1 d . . .
H4B H 0.1867 -0.5178 0.6269 0.066 Uiso 1 1 calc R . .
C5B C 0.2317(3) -0.3514(3) 0.59149(11) 0.0473(7) Uani 1 1 d . . .
H5B H 0.146 -0.3086 0.5932 0.057 Uiso 1 1 calc R . .
C6B C 0.3042(3) -0.1577(3) 0.54485(11) 0.0398(7) Uani 1 1 d . . .
C8B C 0.5837(3) 0.0426(3) 0.61390(10) 0.0376(7) Uani 1 1 d . . .
C9B C 0.6926(3) 0.0279(3) 0.66047(11) 0.0425(7) Uani 1 1 d . . .
C10B C 0.6909(3) -0.0852(3) 0.69048(11) 0.0513(8) Uani 1 1 d . . .
H10B H 0.6177 -0.152 0.6813 0.062 Uiso 1 1 calc R . .
C11B C 0.7929(4) -0.1013(4) 0.73284(12) 0.0663(10) Uani 1 1 d . . .
H11B H 0.7906 -0.1798 0.7523 0.08 Uiso 1 1 calc R . .
C12B C 0.8984(4) -0.0054(4) 0.74756(13) 0.0776(11) Uani 1 1 d . . .
H12B H 0.9686 -0.0169 0.7772 0.093 Uiso 1 1 calc R . .
C13B C 0.9017(4) 0.1070(4) 0.71922(14) 0.0733(10) Uani 1 1 d . . .
H13B H 0.9742 0.1742 0.7294 0.088 Uiso 1 1 calc R . .
C14B C 0.8004(3) 0.1238(3) 0.67582(12) 0.0580(9) Uani 1 1 d . . .
H14B H 0.8048 0.2018 0.6563 0.07 Uiso 1 1 calc R . .
C7B C 0.5752(3) 0.1721(3) 0.58691(12) 0.0614(9) Uani 1 1 d . . .
H7B1 H 0.5322 0.1543 0.5503 0.092 Uiso 1 1 calc R . .
H7B2 H 0.6693 0.2119 0.5891 0.092 Uiso 1 1 calc R . .
H7B3 H 0.5184 0.2354 0.6036 0.092 Uiso 1 1 calc R . .
N1B N 0.3945(2) -0.0522(2) 0.55843(9) 0.0428(6) Uani 1 1 d . . .
N2B N 0.3704(3) -0.5461(2) 0.60885(10) 0.0605(7) Uani 1 1 d . . .
N3B N 0.5016(2) -0.0612(2) 0.60064(9) 0.0424(6) Uani 1 1 d . . .
O1B O 0.1993(2) -0.14911(18) 0.51094(8) 0.0539(6) Uani 1 1 d . . .
H1B H 0.374(3) 0.023(3) 0.5408(11) 0.068(10) Uiso 1 1 d . . .
C1C C 0.7537(3) 0.2013(3) 0.07763(10) 0.0383(7) Uani 1 1 d . . .
C5C C 0.8812(3) 0.1422(3) 0.08445(12) 0.0548(8) Uani 1 1 d . . .
H5C H 0.9585 0.1863 0.074 0.066 Uiso 1 1 calc R . .
C4C C 0.8964(4) 0.0186(3) 0.10655(13) 0.0667(10) Uani 1 1 d . . .
H4C H 0.9865 -0.019 0.1116 0.08 Uiso 1 1 calc R . .
C3C C 0.6732(4) 0.0063(3) 0.11372(16) 0.0861(13) Uani 1 1 d . . .
H3C H 0.5971 -0.0424 0.1232 0.103 Uiso 1 1 calc R . .
C2C C 0.6471(4) 0.1315(3) 0.09328(14) 0.0689(10) Uani 1 1 d . . .
H2C H 0.5568 0.1683 0.0902 0.083 Uiso 1 1 calc R . .
C6C C 0.7394(3) 0.3300(3) 0.04989(11) 0.0451(7) Uani 1 1 d . . .
C8C C 0.5326(3) 0.5269(3) 0.12070(11) 0.0430(7) Uani 1 1 d . . .
C9C C 0.4736(3) 0.5174(3) 0.16901(11) 0.0483(8) Uani 1 1 d . . .
C10C C 0.5156(4) 0.4168(3) 0.20280(12) 0.0612(9) Uani 1 1 d . . .
H10C H 0.5799 0.3522 0.1942 0.073 Uiso 1 1 calc R . .
C11C C 0.4653(4) 0.4084(4) 0.24913(14) 0.0838(12) Uani 1 1 d . . .
H11C H 0.4972 0.3407 0.2726 0.101 Uiso 1 1 calc R . .
C12C C 0.3685(5) 0.4995(5) 0.26057(16) 0.0980(15) Uani 1 1 d . . .
H12C H 0.3323 0.4935 0.2918 0.118 Uiso 1 1 calc R . .
C13C C 0.3247(4) 0.5977(5) 0.22747(16) 0.0890(13) Uani 1 1 d . . .
H13C H 0.2577 0.6597 0.2356 0.107 Uiso 1 1 calc R . .
C14C C 0.3773(3) 0.6081(3) 0.18178(13) 0.0641(9) Uani 1 1 d . . .
H14C H 0.3468 0.6779 0.1591 0.077 Uiso 1 1 calc R . .
C7C C 0.5146(4) 0.6513(3) 0.09067(13) 0.0667(10) Uani 1 1 d . . .
H7C1 H 0.605 0.6993 0.0936 0.1 Uiso 1 1 calc R . .
H7C2 H 0.4491 0.7105 0.1046 0.1 Uiso 1 1 calc R . .
H7C3 H 0.4777 0.6259 0.054 0.1 Uiso 1 1 calc R . .
N1C N 0.6607(3) 0.4312(2) 0.06452(9) 0.0454(6) Uani 1 1 d . . .
N2C N 0.7955(4) -0.0503(3) 0.12098(11) 0.0753(9) Uani 1 1 d . . .
N3C N 0.6005(2) 0.4239(2) 0.10837(9) 0.0436(6) Uani 1 1 d . . .
O1C O 0.7998(2) 0.34336(18) 0.01277(8) 0.0594(6) Uani 1 1 d . . .
C1D C 0.7419(3) 0.7965(3) -0.06666(11) 0.0425(7) Uani 1 1 d . . .
C2D C 0.7189(3) 0.8097(3) -0.12017(11) 0.0464(7) Uani 1 1 d . . .
H2D H 0.7142 0.732 -0.1435 0.056 Uiso 1 1 calc R . .
C3D C 0.7032(3) 0.9373(3) -0.13870(12) 0.0574(9) Uani 1 1 d . . .
H3D H 0.6849 0.9444 -0.1754 0.069 Uiso 1 1 calc R . .
C4D C 0.7354(5) 1.0371(3) -0.05847(14) 0.0843(13) Uani 1 1 d . . .
H4D H 0.7434 1.1171 -0.0363 0.101 Uiso 1 1 calc R . .
C5D C 0.7494(4) 0.9140(3) -0.03567(12) 0.0648(10) Uani 1 1 d . . .
H5D H 0.764 0.9104 0.0011 0.078 Uiso 1 1 calc R . .
C6D C 0.7477(3) 0.6659(3) -0.04051(11) 0.0460(8) Uani 1 1 d . . .
C8D C 0.9589(3) 0.4696(3) -0.10938(11) 0.0450(7) Uani 1 1 d . . .
C9D C 1.0256(3) 0.4844(3) -0.15593(11) 0.0448(7) Uani 1 1 d . . .
C10D C 1.0116(3) 0.6022(3) -0.18323(11) 0.0555(8) Uani 1 1 d . . .
H10D H 0.9599 0.6746 -0.1718 0.067 Uiso 1 1 calc R . .
C11D C 1.0719(4) 0.6149(4) -0.22658(12) 0.0683(10) Uani 1 1 d . . .
H11D H 1.0624 0.6963 -0.2446 0.082 Uiso 1 1 calc R . .
C12D C 1.1457(4) 0.5102(4) -0.24394(13) 0.0744(11) Uani 1 1 d . . .
H12D H 1.1861 0.5189 -0.2741 0.089 Uiso 1 1 calc R . .
C13D C 1.1607(4) 0.3941(4) -0.21771(14) 0.0711(10) Uani 1 1 d . . .
H13D H 1.2121 0.3221 -0.2296 0.085 Uiso 1 1 calc R . .
C14D C 1.1015(3) 0.3806(3) -0.17389(13) 0.0583(9) Uani 1 1 d . . .
H14D H 1.1129 0.2993 -0.1558 0.07 Uiso 1 1 calc R . .
C7D C 0.9730(4) 0.3404(3) -0.08187(13) 0.0725(11) Uani 1 1 d . . .
H7D1 H 0.9528 0.356 -0.0467 0.109 Uiso 1 1 calc R . .
H7D2 H 1.0684 0.3088 -0.0797 0.109 Uiso 1 1 calc R . .
H7D3 H 0.9069 0.2715 -0.1011 0.109 Uiso 1 1 calc R . .
N1D N 0.8193(3) 0.5615(2) -0.05618(9) 0.0471(7) Uani 1 1 d . . .
N2D N 0.7117(3) 1.0506(3) -0.10927(11) 0.0742(9) Uani 1 1 d . . .
N3D N 0.8895(2) 0.5713(2) -0.09747(9) 0.0441(6) Uani 1 1 d . . .
O1D O 0.6867(2) 0.65530(19) -0.00323(8) 0.0643(6) Uani 1 1 d . . .
H1D H 0.819(3) 0.485(3) -0.0384(10) 0.060(9) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   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
C1A C2A 1.378(4) . ?
C1A C5A 1.383(4) . ?
C1A C6A 1.490(3) . ?
C2A C3A 1.371(4) . ?
C2A H2A 0.95 . ?
C3A N2A 1.325(4) . ?
C3A H3A 0.95 . ?
C4A N2A 1.321(4) . ?
C4A C5A 1.380(4) . ?
C4A H4A 0.95 . ?
C5A H5A 0.95 . ?
C6A O1A 1.237(3) . ?
C6A N1A 1.339(3) . ?
C8A N3A 1.284(3) . ?
C8A C9A 1.478(4) . ?
C8A C7A 1.496(3) . ?
C9A C14A 1.380(4) . ?
C9A C10A 1.389(4) . ?
C10A C11A 1.384(4) . ?
C10A H10A 0.95 . ?
C11A C12A 1.368(5) . ?
C11A H11A 0.95 . ?
C12A C13A 1.354(5) . ?
C12A H12A 0.95 . ?
C13A C14A 1.382(4) . ?
C13A H13A 0.95 . ?
C14A H14A 0.95 . ?
C7A H7A1 0.98 . ?
C7A H7A2 0.98 . ?
C7A H7A3 0.98 . ?
N1A N3A 1.382(3) . ?
N1A H1A 0.94(3) . ?
C1B C5B 1.365(4) . ?
C1B C2B 1.387(4) . ?
C1B C6B 1.490(3) . ?
C2B C3B 1.373(4) . ?
C2B H2B 0.95 . ?
C3B N2B 1.327(4) . ?
C3B H3B 0.95 . ?
C4B N2B 1.321(4) . ?
C4B C5B 1.377(4) . ?
C4B H4B 0.95 . ?
C5B H5B 0.95 . ?
C6B O1B 1.235(3) . ?
C6B N1B 1.340(3) . ?
C8B N3B 1.280(3) . ?
C8B C9B 1.480(4) . ?
C8B C7B 1.488(3) . ?
C9B C14B 1.388(4) . ?
C9B C10B 1.398(4) . ?
C10B C11B 1.368(4) . ?
C10B H10B 0.95 . ?
C11B C12B 1.371(5) . ?
C11B H11B 0.95 . ?
C12B C13B 1.368(5) . ?
C12B H12B 0.95 . ?
C13B C14B 1.384(4) . ?
C13B H13B 0.95 . ?
C14B H14B 0.95 . ?
C7B H7B1 0.98 . ?
C7B H7B2 0.98 . ?
C7B H7B3 0.98 . ?
N1B N3B 1.384(3) . ?
N1B H1B 0.90(3) . ?
C1C C2C 1.367(4) . ?
C1C C5C 1.370(4) . ?
C1C C6C 1.492(3) . ?
C5C C4C 1.377(4) . ?
C5C H5C 0.95 . ?
C4C N2C 1.304(4) . ?
C4C H4C 0.95 . ?
C3C N2C 1.314(4) . ?
C3C C2C 1.382(4) . ?
C3C H3C 0.95 . ?
C2C H2C 0.95 . ?
C6C O1C 1.232(3) . ?
C6C N1C 1.354(3) . ?
C8C N3C 1.285(3) . ?
C8C C9C 1.484(4) . ?
C8C C7C 1.487(4) . ?
C9C C10C 1.383(4) . ?
C9C C14C 1.383(4) . ?
C10C C11C 1.391(4) . ?
C10C H10C 0.95 . ?
C11C C12C 1.378(6) . ?
C11C H11C 0.95 . ?
C12C C13C 1.357(5) . ?
C12C H12C 0.95 . ?
C13C C14C 1.389(5) . ?
C13C H13C 0.95 . ?
C14C H14C 0.95 . ?
C7C H7C1 0.98 . ?
C7C H7C2 0.98 . ?
C7C H7C3 0.98 . ?
N1C N3C 1.382(3) . ?
N1C H1C 1.01(3) . ?
C1D C5D 1.374(4) . ?
C1D C2D 1.390(4) . ?
C1D C6D 1.487(4) . ?
C2D C3D 1.375(4) . ?
C2D H2D 0.95 . ?
C3D N2D 1.319(4) . ?
C3D H3D 0.95 . ?
C4D N2D 1.321(4) . ?
C4D C5D 1.379(4) . ?
C4D H4D 0.95 . ?
C5D H5D 0.95 . ?
C6D O1D 1.236(3) . ?
C6D N1D 1.345(3) . ?
C8D N3D 1.280(3) . ?
C8D C9D 1.490(4) . ?
C8D C7D 1.493(4) . ?
C9D C14D 1.388(4) . ?
C9D C10D 1.392(4) . ?
C10D C11D 1.376(4) . ?
C10D H10D 0.95 . ?
C11D C12D 1.377(5) . ?
C11D H11D 0.95 . ?
C12D C13D 1.363(5) . ?
C12D H12D 0.95 . ?
C13D C14D 1.382(4) . ?
C13D H13D 0.95 . ?
C14D H14D 0.95 . ?
C7D H7D1 0.98 . ?
C7D H7D2 0.98 . ?
C7D H7D3 0.98 . ?
N1D N3D 1.383(3) . ?
N1D H1D 0.91(3) . ?

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
C2A C1A C5A 117.5(2) . . ?
C2A C1A C6A 125.7(3) . . ?
C5A C1A C6A 116.8(2) . . ?
C3A C2A C1A 119.1(3) . . ?
C3A C2A H2A 120.4 . . ?
C1A C2A H2A 120.4 . . ?
N2A C3A C2A 124.4(3) . . ?
N2A C3A H3A 117.8 . . ?
C2A C3A H3A 117.8 . . ?
N2A C4A C5A 124.5(3) . . ?
N2A C4A H4A 117.7 . . ?
C5A C4A H4A 117.7 . . ?
C4A C5A C1A 118.5(3) . . ?
C4A C5A H5A 120.7 . . ?
C1A C5A H5A 120.7 . . ?
O1A C6A N1A 120.9(2) . . ?
O1A C6A C1A 118.6(2) . . ?
N1A C6A C1A 120.5(3) . . ?
N3A C8A C9A 116.4(2) . . ?
N3A C8A C7A 124.6(3) . . ?
C9A C8A C7A 119.0(3) . . ?
C14A C9A C10A 117.5(3) . . ?
C14A C9A C8A 121.4(3) . . ?
C10A C9A C8A 120.9(3) . . ?
C11A C10A C9A 120.4(3) . . ?
C11A C10A H10A 119.8 . . ?
C9A C10A H10A 119.8 . . ?
C12A C11A C10A 120.7(3) . . ?
C12A C11A H11A 119.6 . . ?
C10A C11A H11A 119.6 . . ?
C13A C12A C11A 119.6(3) . . ?
C13A C12A H12A 120.2 . . ?
C11A C12A H12A 120.2 . . ?
C12A C13A C14A 120.4(3) . . ?
C12A C13A H13A 119.8 . . ?
C14A C13A H13A 119.8 . . ?
C9A C14A C13A 121.4(3) . . ?
C9A C14A H14A 119.3 . . ?
C13A C14A H14A 119.3 . . ?
C8A C7A H7A1 109.5 . . ?
C8A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C8A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C6A N1A N3A 121.5(2) . . ?
C6A N1A H1A 113.8(17) . . ?
N3A N1A H1A 124.7(17) . . ?
C4A N2A C3A 115.9(3) . . ?
C8A N3A N1A 117.7(2) . . ?
C5B C1B C2B 118.0(3) . . ?
C5B C1B C6B 120.1(3) . . ?
C2B C1B C6B 121.7(3) . . ?
C3B C2B C1B 118.1(3) . . ?
C3B C2B H2B 121 . . ?
C1B C2B H2B 121 . . ?
N2B C3B C2B 125.1(3) . . ?
N2B C3B H3B 117.4 . . ?
C2B C3B H3B 117.4 . . ?
N2B C4B C5B 124.8(3) . . ?
N2B C4B H4B 117.6 . . ?
C5B C4B H4B 117.6 . . ?
C1B C5B C4B 118.9(3) . . ?
C1B C5B H5B 120.6 . . ?
C4B C5B H5B 120.6 . . ?
O1B C6B N1B 121.1(2) . . ?
O1B C6B C1B 119.1(3) . . ?
N1B C6B C1B 119.8(3) . . ?
N3B C8B C9B 115.0(2) . . ?
N3B C8B C7B 125.2(3) . . ?
C9B C8B C7B 119.8(3) . . ?
C14B C9B C10B 117.4(3) . . ?
C14B C9B C8B 121.9(3) . . ?
C10B C9B C8B 120.6(3) . . ?
C11B C10B C9B 121.1(3) . . ?
C11B C10B H10B 119.5 . . ?
C9B C10B H10B 119.5 . . ?
C10B C11B C12B 120.7(3) . . ?
C10B C11B H11B 119.6 . . ?
C12B C11B H11B 119.6 . . ?
C13B C12B C11B 119.4(3) . . ?
C13B C12B H12B 120.3 . . ?
C11B C12B H12B 120.3 . . ?
C12B C13B C14B 120.6(4) . . ?
C12B C13B H13B 119.7 . . ?
C14B C13B H13B 119.7 . . ?
C13B C14B C9B 120.8(3) . . ?
C13B C14B H14B 119.6 . . ?
C9B C14B H14B 119.6 . . ?
C8B C7B H7B1 109.5 . . ?
C8B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
C8B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C6B N1B N3B 118.9(2) . . ?
C6B N1B H1B 115.4(19) . . ?
N3B N1B H1B 125.3(19) . . ?
C4B N2B C3B 115.2(3) . . ?
C8B N3B N1B 117.8(2) . . ?
C2C C1C C5C 116.9(3) . . ?
C2C C1C C6C 125.2(3) . . ?
C5C C1C C6C 117.6(3) . . ?
C1C C5C C4C 119.6(3) . . ?
C1C C5C H5C 120.2 . . ?
C4C C5C H5C 120.2 . . ?
N2C C4C C5C 124.4(3) . . ?
N2C C4C H4C 117.8 . . ?
C5C C4C H4C 117.8 . . ?
N2C C3C C2C 124.8(3) . . ?
N2C C3C H3C 117.6 . . ?
C2C C3C H3C 117.6 . . ?
C1C C2C C3C 118.7(3) . . ?
C1C C2C H2C 120.7 . . ?
C3C C2C H2C 120.7 . . ?
O1C C6C N1C 119.8(2) . . ?
O1C C6C C1C 119.0(2) . . ?
N1C C6C C1C 121.2(3) . . ?
N3C C8C C9C 115.5(2) . . ?
N3C C8C C7C 124.1(3) . . ?
C9C C8C C7C 120.3(3) . . ?
C10C C9C C14C 118.3(3) . . ?
C10C C9C C8C 120.1(3) . . ?
C14C C9C C8C 121.6(3) . . ?
C9C C10C C11C 121.1(3) . . ?
C9C C10C H10C 119.4 . . ?
C11C C10C H10C 119.4 . . ?
C12C C11C C10C 119.2(4) . . ?
C12C C11C H11C 120.4 . . ?
C10C C11C H11C 120.4 . . ?
C13C C12C C11C 120.4(4) . . ?
C13C C12C H12C 119.8 . . ?
C11C C12C H12C 119.8 . . ?
C12C C13C C14C 120.5(4) . . ?
C12C C13C H13C 119.8 . . ?
C14C C13C H13C 119.8 . . ?
C9C C14C C13C 120.5(4) . . ?
C9C C14C H14C 119.8 . . ?
C13C C14C H14C 119.8 . . ?
C8C C7C H7C1 109.5 . . ?
C8C C7C H7C2 109.5 . . ?
H7C1 C7C H7C2 109.5 . . ?
C8C C7C H7C3 109.5 . . ?
H7C1 C7C H7C3 109.5 . . ?
H7C2 C7C H7C3 109.5 . . ?
C6C N1C N3C 121.2(2) . . ?
C6C N1C H1C 116(2) . . ?
N3C N1C H1C 123(2) . . ?
C4C N2C C3C 115.7(3) . . ?
C8C N3C N1C 117.1(2) . . ?
C5D C1D C2D 117.0(3) . . ?
C5D C1D C6D 117.4(3) . . ?
C2D C1D C6D 125.4(3) . . ?
C3D C2D C1D 118.6(3) . . ?
C3D C2D H2D 120.7 . . ?
C1D C2D H2D 120.7 . . ?
N2D C3D C2D 124.7(3) . . ?
N2D C3D H3D 117.6 . . ?
C2D C3D H3D 117.6 . . ?
N2D C4D C5D 124.1(3) . . ?
N2D C4D H4D 118 . . ?
C5D C4D H4D 118 . . ?
C1D C5D C4D 119.4(3) . . ?
C1D C5D H5D 120.3 . . ?
C4D C5D H5D 120.3 . . ?
O1D C6D N1D 120.1(3) . . ?
O1D C6D C1D 118.6(3) . . ?
N1D C6D C1D 121.3(3) . . ?
N3D C8D C9D 115.1(2) . . ?
N3D C8D C7D 125.5(3) . . ?
C9D C8D C7D 119.4(2) . . ?
C14D C9D C10D 118.0(3) . . ?
C14D C9D C8D 121.2(3) . . ?
C10D C9D C8D 120.8(3) . . ?
C11D C10D C9D 120.7(3) . . ?
C11D C10D H10D 119.7 . . ?
C9D C10D H10D 119.7 . . ?
C10D C11D C12D 120.3(3) . . ?
C10D C11D H11D 119.8 . . ?
C12D C11D H11D 119.8 . . ?
C13D C12D C11D 119.9(3) . . ?
C13D C12D H12D 120.1 . . ?
C11D C12D H12D 120.1 . . ?
C12D C13D C14D 120.4(3) . . ?
C12D C13D H13D 119.8 . . ?
C14D C13D H13D 119.8 . . ?
C13D C14D C9D 120.8(3) . . ?
C13D C14D H14D 119.6 . . ?
C9D C14D H14D 119.6 . . ?
C8D C7D H7D1 109.5 . . ?
C8D C7D H7D2 109.5 . . ?
H7D1 C7D H7D2 109.5 . . ?
C8D C7D H7D3 109.5 . . ?
H7D1 C7D H7D3 109.5 . . ?
H7D2 C7D H7D3 109.5 . . ?
C6D N1D N3D 121.2(2) . . ?
C6D N1D H1D 116.8(18) . . ?
N3D N1D H1D 122.0(18) . . ?
C3D N2D C4D 116.1(3) . . ?
C8D N3D N1D 118.0(2) . . ?

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
C5A C1A C2A C3A 1.4(4) . . . . ?
C6A C1A C2A C3A -175.1(3) . . . . ?
C1A C2A C3A N2A -2.9(5) . . . . ?
N2A C4A C5A C1A -1.3(5) . . . . ?
C2A C1A C5A C4A 0.6(4) . . . . ?
C6A C1A C5A C4A 177.3(3) . . . . ?
C2A C1A C6A O1A 131.6(3) . . . . ?
C5A C1A C6A O1A -44.9(4) . . . . ?
C2A C1A C6A N1A -49.6(4) . . . . ?
C5A C1A C6A N1A 133.9(3) . . . . ?
N3A C8A C9A C14A -178.4(3) . . . . ?
C7A C8A C9A C14A 3.5(4) . . . . ?
N3A C8A C9A C10A 5.1(4) . . . . ?
C7A C8A C9A C10A -173.1(3) . . . . ?
C14A C9A C10A C11A 0.5(5) . . . . ?
C8A C9A C10A C11A 177.2(3) . . . . ?
C9A C10A C11A C12A -1.0(5) . . . . ?
C10A C11A C12A C13A 1.3(6) . . . . ?
C11A C12A C13A C14A -1.1(6) . . . . ?
C10A C9A C14A C13A -0.3(4) . . . . ?
C8A C9A C14A C13A -176.9(3) . . . . ?
C12A C13A C14A C9A 0.6(5) . . . . ?
O1A C6A N1A N3A -178.2(2) . . . . ?
C1A C6A N1A N3A 3.0(4) . . . . ?
C5A C4A N2A C3A 0.0(5) . . . . ?
C2A C3A N2A C4A 2.2(5) . . . . ?
C9A C8A N3A N1A -175.3(2) . . . . ?
C7A C8A N3A N1A 2.7(4) . . . . ?
C6A N1A N3A C8A -175.1(2) . . . . ?
C5B C1B C2B C3B 0.3(4) . . . . ?
C6B C1B C2B C3B -173.9(3) . . . . ?
C1B C2B C3B N2B -0.6(5) . . . . ?
C2B C1B C5B C4B 1.0(4) . . . . ?
C6B C1B C5B C4B 175.2(3) . . . . ?
N2B C4B C5B C1B -2.1(5) . . . . ?
C5B C1B C6B O1B -53.1(4) . . . . ?
C2B C1B C6B O1B 120.9(3) . . . . ?
C5B C1B C6B N1B 128.5(3) . . . . ?
C2B C1B C6B N1B -57.4(4) . . . . ?
N3B C8B C9B C14B 171.4(3) . . . . ?
C7B C8B C9B C14B -9.5(4) . . . . ?
N3B C8B C9B C10B -7.8(4) . . . . ?
C7B C8B C9B C10B 171.3(3) . . . . ?
C14B C9B C10B C11B -0.9(4) . . . . ?
C8B C9B C10B C11B 178.4(3) . . . . ?
C9B C10B C11B C12B 1.2(5) . . . . ?
C10B C11B C12B C13B -0.4(5) . . . . ?
C11B C12B C13B C14B -0.5(5) . . . . ?
C12B C13B C14B C9B 0.8(5) . . . . ?
C10B C9B C14B C13B -0.1(4) . . . . ?
C8B C9B C14B C13B -179.3(3) . . . . ?
O1B C6B N1B N3B 172.6(2) . . . . ?
C1B C6B N1B N3B -9.1(4) . . . . ?
C5B C4B N2B C3B 1.7(5) . . . . ?
C2B C3B N2B C4B -0.3(5) . . . . ?
C9B C8B N3B N1B 177.8(2) . . . . ?
C7B C8B N3B N1B -1.2(4) . . . . ?
C6B N1B N3B C8B -177.8(2) . . . . ?
C2C C1C C5C C4C -0.4(5) . . . . ?
C6C C1C C5C C4C -175.5(3) . . . . ?
C1C C5C C4C N2C 1.5(5) . . . . ?
C5C C1C C2C C3C -1.3(5) . . . . ?
C6C C1C C2C C3C 173.3(3) . . . . ?
N2C C3C C2C C1C 2.3(6) . . . . ?
C2C C1C C6C O1C -136.6(3) . . . . ?
C5C C1C C6C O1C 38.0(4) . . . . ?
C2C C1C C6C N1C 42.8(4) . . . . ?
C5C C1C C6C N1C -142.6(3) . . . . ?
N3C C8C C9C C10C 12.8(4) . . . . ?
C7C C8C C9C C10C -165.7(3) . . . . ?
N3C C8C C9C C14C -167.8(3) . . . . ?
C7C C8C C9C C14C 13.8(4) . . . . ?
C14C C9C C10C C11C -1.6(5) . . . . ?
C8C C9C C10C C11C 177.9(3) . . . . ?
C9C C10C C11C C12C 2.1(5) . . . . ?
C10C C11C C12C C13C -1.2(6) . . . . ?
C11C C12C C13C C14C -0.3(6) . . . . ?
C10C C9C C14C C13C 0.1(5) . . . . ?
C8C C9C C14C C13C -179.4(3) . . . . ?
C12C C13C C14C C9C 0.8(6) . . . . ?
O1C C6C N1C N3C -174.9(3) . . . . ?
C1C C6C N1C N3C 5.7(4) . . . . ?
C5C C4C N2C C3C -0.7(5) . . . . ?
C2C C3C N2C C4C -1.3(6) . . . . ?
C9C C8C N3C N1C -178.0(2) . . . . ?
C7C C8C N3C N1C 0.4(4) . . . . ?
C6C N1C N3C C8C 177.0(3) . . . . ?
C5D C1D C2D C3D -1.0(4) . . . . ?
C6D C1D C2D C3D 173.9(3) . . . . ?
C1D C2D C3D N2D 1.8(5) . . . . ?
C2D C1D C5D C4D -0.6(5) . . . . ?
C6D C1D C5D C4D -175.9(3) . . . . ?
N2D C4D C5D C1D 1.6(6) . . . . ?
C5D C1D C6D O1D 38.5(4) . . . . ?
C2D C1D C6D O1D -136.4(3) . . . . ?
C5D C1D C6D N1D -140.5(3) . . . . ?
C2D C1D C6D N1D 44.7(4) . . . . ?
N3D C8D C9D C14D -178.6(3) . . . . ?
C7D C8D C9D C14D -0.5(4) . . . . ?
N3D C8D C9D C10D 0.4(4) . . . . ?
C7D C8D C9D C10D 178.4(3) . . . . ?
C14D C9D C10D C11D -0.2(5) . . . . ?
C8D C9D C10D C11D -179.2(3) . . . . ?
C9D C10D C11D C12D 0.8(5) . . . . ?
C10D C11D C12D C13D -0.8(5) . . . . ?
C11D C12D C13D C14D 0.3(5) . . . . ?
C12D C13D C14D C9D 0.2(5) . . . . ?
C10D C9D C14D C13D -0.3(5) . . . . ?
C8D C9D C14D C13D 178.7(3) . . . . ?
O1D C6D N1D N3D -179.4(3) . . . . ?
C1D C6D N1D N3D -0.5(4) . . . . ?
C2D C3D N2D C4D -0.8(5) . . . . ?
C5D C4D N2D C3D -0.9(6) . . . . ?
C9D C8D N3D N1D 176.9(2) . . . . ?
C7D C8D N3D N1D -1.0(4) . . . . ?
C6D N1D N3D C8D 178.0(3) . . . . ?

####################################################################### 
# 
# 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_14a_form6_p
_database_code_depnum_ccdc_archive 'CCDC 1022894'
_audit_update_record             
;
2014-09-04 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;


_audit_creation_date             2014-09-04T11:08:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
'isonicotinic acid-(1-phenyl-ethylidenehydrazide)'
_chemical_formula_moiety         'C14 H13 N3 O'
_chemical_formula_sum            'C14 H13 N3 O'
_chemical_formula_weight         239.27
_chemical_melting_point          423.15

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'
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                   10.6217(16)
_cell_length_b                   14.442(2)
_cell_length_c                   8.2589(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.623(5)
_cell_angle_gamma                90
_cell_volume                     1193.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2025
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      23.28

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

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.449
0 0 -1 0.503
0 1 0 0.02
0 -1 0 0.015
1 0 0 0.023
-1 0 0 0.007

_exptl_special_details           ?

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

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.989

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.1089
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_number            12494
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         23.31
_diffrn_reflns_theta_full        23.31
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             1723
_reflns_number_gt                1183
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX3 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;

#----------------------------------------------------------------------------#
#                   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)+(0.0523P)²+0.5073P] 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_number_reflns         1723
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.234
_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 0.0033 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'
O O 0.0106 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 0.9991(3) 0.3435(2) 0.6954(4) 0.0253(7) Uani 1 1 d . . .
C2 C 1.0862(3) 0.2852(2) 0.8133(4) 0.0311(8) Uani 1 1 d . . .
H2 H 1.0843 0.2203 0.794 0.037 Uiso 1 1 calc R . .
C3 C 1.1760(3) 0.3235(3) 0.9600(4) 0.0404(9) Uani 1 1 d . . .
H3 H 1.2358 0.2831 1.0405 0.048 Uiso 1 1 calc R . .
C4 C 1.0987(3) 0.4684(2) 0.8798(4) 0.0407(9) Uani 1 1 d . . .
H4 H 1.1015 0.5329 0.9034 0.049 Uiso 1 1 calc R . .
C5 C 1.0070(3) 0.4372(2) 0.7282(4) 0.0339(8) Uani 1 1 d . . .
H5 H 0.9505 0.4794 0.6482 0.041 Uiso 1 1 calc R . .
C6 C 0.9020(3) 0.3098(2) 0.5302(4) 0.0242(7) Uani 1 1 d . . .
C7 C 0.6166(3) 0.1261(2) 0.5677(4) 0.0363(8) Uani 1 1 d . . .
H7A H 0.6919 0.1483 0.6655 0.054 Uiso 0.5 1 calc PR . .
H7B H 0.6135 0.0583 0.5702 0.054 Uiso 0.5 1 calc PR . .
H7C H 0.5331 0.1515 0.5749 0.054 Uiso 0.5 1 calc PR . .
H7D H 0.5337 0.0904 0.5416 0.054 Uiso 0.5 1 calc PR . .
H7E H 0.6122 0.1804 0.6368 0.054 Uiso 0.5 1 calc PR . .
H7F H 0.6926 0.0873 0.6322 0.054 Uiso 0.5 1 calc PR . .
C8 C 0.6341(3) 0.1571(2) 0.4038(4) 0.0254(7) Uani 1 1 d . . .
C9 C 0.5309(3) 0.13124(19) 0.2384(4) 0.0249(7) Uani 1 1 d . . .
C10 C 0.5565(3) 0.1346(2) 0.0856(4) 0.0327(8) Uani 1 1 d . . .
H10 H 0.6431 0.1515 0.0862 0.039 Uiso 1 1 calc R . .
C11 C 0.4580(3) 0.1136(2) -0.0687(4) 0.0375(9) Uani 1 1 d . . .
H11 H 0.477 0.1169 -0.1731 0.045 Uiso 1 1 calc R . .
C12 C 0.3330(3) 0.0880(2) -0.0713(4) 0.0380(9) Uani 1 1 d . . .
H12 H 0.2653 0.0735 -0.1772 0.046 Uiso 1 1 calc R . .
C13 C 0.3064(3) 0.0835(2) 0.0791(4) 0.0401(9) Uani 1 1 d . . .
H13 H 0.2201 0.0654 0.0778 0.048 Uiso 1 1 calc R . .
C14 C 0.4040(3) 0.1051(2) 0.2328(4) 0.0323(8) Uani 1 1 d . . .
H14 H 0.384 0.102 0.3365 0.039 Uiso 1 1 calc R . .
N1 N 0.8277(2) 0.23631(17) 0.5409(3) 0.0256(6) Uani 1 1 d . . .
H1 H 0.829(3) 0.216(2) 0.643(5) 0.041(10) Uiso 1 1 d . . .
N2 N 1.1837(3) 0.4135(2) 0.9951(4) 0.0447(8) Uani 1 1 d . . .
N3 N 0.7303(2) 0.20706(16) 0.3904(3) 0.0253(6) Uani 1 1 d . . .
O1 O 0.8925(2) 0.34926(14) 0.3948(3) 0.0313(6) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   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 C5 1.376(4) . ?
C1 C2 1.381(4) . ?
C1 C6 1.489(4) . ?
C2 C3 1.381(4) . ?
C2 H2 0.95 . ?
C3 N2 1.327(4) . ?
C3 H3 0.95 . ?
C4 N2 1.331(4) . ?
C4 C5 1.378(4) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
C6 O1 1.229(3) . ?
C6 N1 1.343(4) . ?
C7 C8 1.495(4) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C7 H7D 0.98 . ?
C7 H7E 0.98 . ?
C7 H7F 0.98 . ?
C8 N3 1.286(4) . ?
C8 C9 1.484(4) . ?
C9 C10 1.378(4) . ?
C9 C14 1.385(4) . ?
C10 C11 1.384(4) . ?
C10 H10 0.95 . ?
C11 C12 1.371(4) . ?
C11 H11 0.95 . ?
C12 C13 1.365(5) . ?
C12 H12 0.95 . ?
C13 C14 1.378(4) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
N1 N3 1.388(3) . ?
N1 H1 0.89(3) . ?

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
C5 C1 C2 118.6(3) . . ?
C5 C1 C6 118.7(3) . . ?
C2 C1 C6 122.7(3) . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
N2 C3 C2 123.9(3) . . ?
N2 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
N2 C4 C5 123.9(3) . . ?
N2 C4 H4 118.1 . . ?
C5 C4 H4 118.1 . . ?
C1 C5 C4 118.6(3) . . ?
C1 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
O1 C6 N1 123.8(3) . . ?
O1 C6 C1 120.1(3) . . ?
N1 C6 C1 116.1(3) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C7 H7D 109.5 . . ?
H7A C7 H7D 141.1 . . ?
H7B C7 H7D 56.3 . . ?
H7C C7 H7D 56.3 . . ?
C8 C7 H7E 109.5 . . ?
H7A C7 H7E 56.3 . . ?
H7B C7 H7E 141.1 . . ?
H7C C7 H7E 56.3 . . ?
H7D C7 H7E 109.5 . . ?
C8 C7 H7F 109.5 . . ?
H7A C7 H7F 56.3 . . ?
H7B C7 H7F 56.3 . . ?
H7C C7 H7F 141.1 . . ?
H7D C7 H7F 109.5 . . ?
H7E C7 H7F 109.5 . . ?
N3 C8 C9 115.1(3) . . ?
N3 C8 C7 126.1(3) . . ?
C9 C8 C7 118.7(3) . . ?
C10 C9 C14 117.9(3) . . ?
C10 C9 C8 121.5(3) . . ?
C14 C9 C8 120.6(3) . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C6 N1 N3 117.3(3) . . ?
C6 N1 H1 120(2) . . ?
N3 N1 H1 121(2) . . ?
C3 N2 C4 116.7(3) . . ?
C8 N3 N1 117.9(2) . . ?

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
C5 C1 C2 C3 0.9(5) . . . . ?
C6 C1 C2 C3 177.6(3) . . . . ?
C1 C2 C3 N2 0.2(5) . . . . ?
C2 C1 C5 C4 -1.9(5) . . . . ?
C6 C1 C5 C4 -178.8(3) . . . . ?
N2 C4 C5 C1 2.1(5) . . . . ?
C5 C1 C6 O1 45.0(4) . . . . ?
C2 C1 C6 O1 -131.8(3) . . . . ?
C5 C1 C6 N1 -134.3(3) . . . . ?
C2 C1 C6 N1 49.0(4) . . . . ?
N3 C8 C9 C10 19.6(4) . . . . ?
C7 C8 C9 C10 -162.0(3) . . . . ?
N3 C8 C9 C14 -158.8(3) . . . . ?
C7 C8 C9 C14 19.7(4) . . . . ?
C14 C9 C10 C11 0.8(4) . . . . ?
C8 C9 C10 C11 -177.6(3) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C12 C13 C14 C9 -0.4(5) . . . . ?
C10 C9 C14 C13 -0.3(4) . . . . ?
C8 C9 C14 C13 178.2(3) . . . . ?
O1 C6 N1 N3 -3.3(4) . . . . ?
C1 C6 N1 N3 175.9(2) . . . . ?
C2 C3 N2 C4 -0.1(5) . . . . ?
C5 C4 N2 C3 -1.1(5) . . . . ?
C9 C8 N3 N1 177.8(2) . . . . ?
C7 C8 N3 N1 -0.5(4) . . . . ?
C6 N1 N3 C8 -159.6(3) . . . . ?

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
N1 H1 O1 0.89(3) 2.17(4) 3.032(3) 162(3) 4_566

_exptl_crystal_recrystallization_method 'From the Melt'
