# Electronic Supplementary Material (ESI) for ChemComm.
# 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_AY-256
_database_code_depnum_ccdc_archive 'CCDC 1038678'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_date             2014-11-25T12:49:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13  H10  N2  O1'
_chemical_formula_sum            'C13 H10 N2 O'
_chemical_formula_weight         210.23

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.9438(17)
_cell_length_b                   6.3301(6)
_cell_length_c                   19.758(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.492(3)
_cell_angle_gamma                90
_cell_volume                     2058.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_number            6639
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         25.171
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_number_total             1854
_reflns_number_gt                1506
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²+0.8824P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1854
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.098
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.68337(6) 0.93182(16) 0.43225(6) 0.0293(3) Uani 1 d . .
N002 N 0.65463(7) 0.61914(19) 0.47259(7) 0.0235(3) Uani 1 d . .
H002 H 0.7035 0.6166 0.5056 0.028 Uiso 1 calc . .
N003 N 0.43028(9) 0.1594(2) 0.42138(8) 0.0364(4) Uani 1 d . .
C1 C 0.63305(9) 0.7885(2) 0.42458(8) 0.0238(4) Uani 1 d . .
C4 C 0.52859(9) 0.4506(2) 0.41711(8) 0.0231(4) Uani 1 d . .
C5 C 0.60553(9) 0.4573(2) 0.47208(8) 0.0233(4) Uani 1 d . .
C3 C 0.50235(9) 0.6128(2) 0.36166(8) 0.0226(3) Uani 1 d . .
C2 C 0.55326(9) 0.7779(2) 0.36767(8) 0.0245(4) Uani 1 d . .
H2 H 0.5354 0.8873 0.3335 0.029 Uiso 1 calc . .
C9 C 0.40318(9) 0.4088(2) 0.25614(8) 0.0263(4) Uani 1 d . .
H9 H 0.4385 0.2942 0.2706 0.032 Uiso 1 calc . .
C7 C 0.47450(9) 0.2871(2) 0.41898(8) 0.0251(4) Uani 1 d . .
C8 C 0.42274(9) 0.5944(2) 0.29762(8) 0.0238(4) Uani 1 d . .
C13 C 0.36866(9) 0.7631(2) 0.27612(8) 0.0273(4) Uani 1 d . .
H13 H 0.3811 0.888 0.3032 0.033 Uiso 1 calc . .
C10 C 0.33184(9) 0.3938(3) 0.19380(9) 0.0300(4) Uani 1 d . .
H10 H 0.3199 0.2709 0.1657 0.036 Uiso 1 calc . .
C12 C 0.29642(9) 0.7455(3) 0.21458(9) 0.0310(4) Uani 1 d . .
H12 H 0.26 0.8577 0.201 0.037 Uiso 1 calc . .
C6 C 0.63965(10) 0.2984(3) 0.53229(9) 0.0309(4) Uani 1 d . .
H6A H 0.6832 0.2232 0.5264 0.046 Uiso 1 calc . .
H6B H 0.5978 0.2006 0.5301 0.046 Uiso 1 calc . .
H6C H 0.6599 0.369 0.5792 0.046 Uiso 1 calc . .
C11 C 0.27813(9) 0.5620(3) 0.17318(9) 0.0318(4) Uani 1 d . .
H11 H 0.2298 0.5516 0.1315 0.038 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
O001 C1 1.2458(17) . ?
N002 C5 1.3487(18) . ?
N002 C1 1.3808(19) . ?
N002 H002 0.86 . ?
N003 C7 1.1472(19) . ?
C1 C2 1.427(2) . ?
C4 C5 1.375(2) . ?
C4 C7 1.430(2) . ?
C4 C3 1.437(2) . ?
C5 C6 1.490(2) . ?
C3 C2 1.362(2) . ?
C3 C8 1.488(2) . ?
C2 H2 0.93 . ?
C9 C10 1.381(2) . ?
C9 C8 1.395(2) . ?
C9 H9 0.93 . ?
C8 C13 1.391(2) . ?
C13 C12 1.384(2) . ?
C13 H13 0.93 . ?
C10 C11 1.384(2) . ?
C10 H10 0.93 . ?
C12 C11 1.383(2) . ?
C12 H12 0.93 . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
C11 H11 0.93 . ?

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 N002 C1 125.54(13) . . ?
C5 N002 H002 117.2 . . ?
C1 N002 H002 117.2 . . ?
O001 C1 N002 119.38(13) . . ?
O001 C1 C2 125.53(14) . . ?
N002 C1 C2 115.05(13) . . ?
C5 C4 C7 118.68(13) . . ?
C5 C4 C3 120.06(13) . . ?
C7 C4 C3 121.17(13) . . ?
N002 C5 C4 118.44(13) . . ?
N002 C5 C6 116.58(13) . . ?
C4 C5 C6 124.98(13) . . ?
C2 C3 C4 118.51(14) . . ?
C2 C3 C8 121.18(13) . . ?
C4 C3 C8 120.26(13) . . ?
C3 C2 C1 122.18(14) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C10 C9 C8 120.55(15) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
N003 C7 C4 178.26(16) . . ?
C13 C8 C9 119.06(14) . . ?
C13 C8 C3 121.07(13) . . ?
C9 C8 C3 119.81(13) . . ?
C12 C13 C8 120.13(15) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C9 C10 C11 119.93(15) . . ?
C9 C10 H10 120 . . ?
C11 C10 H10 120 . . ?
C13 C12 C11 120.38(15) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C11 C10 119.92(15) . . ?
C12 C11 H11 120 . . ?
C10 C11 H11 120 . . ?



# END of CIF
####################################################################### 
# 
# 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_AV-237
_database_code_depnum_ccdc_archive 'CCDC 1038679'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_date             2014-09-09T23:39:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13  H12  N2  O1'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.9282(17)
_cell_length_b                   6.0959(5)
_cell_length_c                   20.6755(19)
_cell_angle_alpha                90
_cell_angle_beta                 116.768(5)
_cell_angle_gamma                90
_cell_volume                     2130.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    106(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      106(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_number            6179
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.553
_diffrn_reflns_theta_max         30.564
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_number_total             3261
_reflns_number_gt                2734
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0705P)²+1.7791P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3261
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1358
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.27
_refine_diff_density_rms         0.06

#----------------------------------------------------------------------------#
#                   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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.00349(5) 0.31320(14) 0.07175(5) 0.01981(19) Uani 1 d . .
N1 N 0.93342(6) 0.62447(16) 0.02921(5) 0.0170(2) Uani 1 d . .
H1 H 0.9485 0.6291 -0.0053 0.02 Uiso 1 calc . .
N2 N 0.75268(6) 1.07509(18) 0.07344(6) 0.0222(2) Uani 1 d . .
C1 C 0.88346(6) 0.78957(18) 0.03037(6) 0.0151(2) Uani 1 d . .
C2 C 0.85183(6) 0.77937(18) 0.07727(6) 0.0157(2) Uani 1 d . .
C3 C 0.86233(7) 0.57797(19) 0.12429(6) 0.0169(2) Uani 1 d . .
H10 H 0.8185 0.4735 0.0959 0.02 Uiso 1 calc . .
C4 C 0.85913(7) 0.6260(2) 0.19505(6) 0.0180(2) Uani 1 d . .
C5 C 0.82528(7) 0.4714(2) 0.22175(6) 0.0214(2) Uani 1 d . .
H9 H 0.8027 0.3421 0.1946 0.026 Uiso 1 calc . .
C6 C 0.82413(8) 0.5038(2) 0.28772(7) 0.0238(3) Uani 1 d . .
H8 H 0.8006 0.3967 0.3053 0.029 Uiso 1 calc . .
C7 C 0.85706(7) 0.6912(2) 0.32809(7) 0.0235(3) Uani 1 d . .
H2 H 0.8564 0.7119 0.3733 0.028 Uiso 1 calc . .
C8 C 0.86676(7) 0.9612(2) -0.02592(7) 0.0202(2) Uani 1 d . .
H3 H 0.8344 1.0773 -0.0199 0.03 Uiso 1 calc . .
H5 H 0.8382 0.8955 -0.0741 0.03 Uiso 1 calc . .
H4 H 0.9167 1.0237 -0.0208 0.03 Uiso 1 calc . .
C9 C 0.89115(8) 0.8490(2) 0.30217(7) 0.0232(3) Uani 1 d . .
H7 H 0.9135 0.9782 0.3294 0.028 Uiso 1 calc . .
C10 C 0.89214(7) 0.8156(2) 0.23563(7) 0.0210(2) Uani 1 d . .
H6 H 0.9154 0.9227 0.2178 0.025 Uiso 1 calc . .
C11 C 0.94063(7) 0.46421(19) 0.13988(6) 0.0184(2) Uani 1 d . .
H11 H 0.9839 0.5409 0.1807 0.022 Uiso 1 calc . .
H12 H 0.9386 0.3121 0.1557 0.022 Uiso 1 calc . .
C12 C 0.96083(6) 0.45607(18) 0.07739(6) 0.0155(2) Uani 1 d . .
C13 C 0.79730(6) 0.94483(18) 0.07463(6) 0.0165(2) Uani 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
O1 C12 1.2285(13) . ?
N1 C12 1.3601(15) . ?
N1 C1 1.3886(14) . ?
N1 H1 0.88 . ?
N2 C13 1.1514(15) . ?
C1 C2 1.3510(15) . ?
C1 C8 1.4890(16) . ?
C2 C13 1.4265(15) . ?
C2 C3 1.5225(16) . ?
C3 C4 1.5196(15) . ?
C3 C11 1.5333(15) . ?
C3 H10 1 . ?
C4 C5 1.3861(17) . ?
C4 C10 1.3996(17) . ?
C5 C6 1.3880(16) . ?
C5 H9 0.95 . ?
C6 C7 1.3863(19) . ?
C6 H8 0.95 . ?
C7 C9 1.3930(19) . ?
C7 H2 0.95 . ?
C8 H3 0.98 . ?
C8 H5 0.98 . ?
C8 H4 0.98 . ?
C9 C10 1.3992(17) . ?
C9 H7 0.95 . ?
C10 H6 0.95 . ?
C11 C12 1.5042(15) . ?
C11 H11 0.99 . ?
C11 H12 0.99 . ?

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
C12 N1 C1 124.92(9) . . ?
C12 N1 H1 117.5 . . ?
C1 N1 H1 117.5 . . ?
C2 C1 N1 120.29(10) . . ?
C2 C1 C8 125.91(10) . . ?
N1 C1 C8 113.71(9) . . ?
C1 C2 C13 119.14(10) . . ?
C1 C2 C3 121.52(10) . . ?
C13 C2 C3 118.60(9) . . ?
C4 C3 C2 114.15(9) . . ?
C4 C3 C11 109.79(9) . . ?
C2 C3 C11 109.55(9) . . ?
C4 C3 H10 107.7 . . ?
C2 C3 H10 107.7 . . ?
C11 C3 H10 107.7 . . ?
C5 C4 C10 118.97(11) . . ?
C5 C4 C3 118.59(11) . . ?
C10 C4 C3 122.38(10) . . ?
C4 C5 C6 120.63(12) . . ?
C4 C5 H9 119.7 . . ?
C6 C5 H9 119.7 . . ?
C7 C6 C5 120.46(12) . . ?
C7 C6 H8 119.8 . . ?
C5 C6 H8 119.8 . . ?
C6 C7 C9 119.88(11) . . ?
C6 C7 H2 120.1 . . ?
C9 C7 H2 120.1 . . ?
C1 C8 H3 109.5 . . ?
C1 C8 H5 109.5 . . ?
H3 C8 H5 109.5 . . ?
C1 C8 H4 109.5 . . ?
H3 C8 H4 109.5 . . ?
H5 C8 H4 109.5 . . ?
C7 C9 C10 119.43(12) . . ?
C7 C9 H7 120.3 . . ?
C10 C9 H7 120.3 . . ?
C9 C10 C4 120.63(11) . . ?
C9 C10 H6 119.7 . . ?
C4 C10 H6 119.7 . . ?
C12 C11 C3 115.46(9) . . ?
C12 C11 H11 108.4 . . ?
C3 C11 H11 108.4 . . ?
C12 C11 H12 108.4 . . ?
C3 C11 H12 108.4 . . ?
H11 C11 H12 107.5 . . ?
O1 C12 N1 121.04(10) . . ?
O1 C12 C11 122.50(10) . . ?
N1 C12 C11 116.33(9) . . ?
N2 C13 C2 178.34(12) . . ?

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
C12 N1 C1 C2 -6.80(17) . . . . ?
C12 N1 C1 C8 176.32(11) . . . . ?
N1 C1 C2 C13 -176.59(10) . . . . ?
C8 C1 C2 C13 -0.11(18) . . . . ?
N1 C1 C2 C3 -6.61(16) . . . . ?
C8 C1 C2 C3 169.87(11) . . . . ?
C1 C2 C3 C4 152.64(10) . . . . ?
C13 C2 C3 C4 -37.33(14) . . . . ?
C1 C2 C3 C11 29.06(14) . . . . ?
C13 C2 C3 C11 -160.91(10) . . . . ?
C2 C3 C4 C5 144.94(11) . . . . ?
C11 C3 C4 C5 -91.62(12) . . . . ?
C2 C3 C4 C10 -37.92(15) . . . . ?
C11 C3 C4 C10 85.53(13) . . . . ?
C10 C4 C5 C6 -0.06(18) . . . . ?
C3 C4 C5 C6 177.18(11) . . . . ?
C4 C5 C6 C7 -0.17(19) . . . . ?
C5 C6 C7 C9 0.39(19) . . . . ?
C6 C7 C9 C10 -0.38(19) . . . . ?
C7 C9 C10 C4 0.14(18) . . . . ?
C5 C4 C10 C9 0.07(18) . . . . ?
C3 C4 C10 C9 -177.06(11) . . . . ?
C4 C3 C11 C12 -165.74(10) . . . . ?
C2 C3 C11 C12 -39.64(13) . . . . ?
C1 N1 C12 O1 178.30(10) . . . . ?
C1 N1 C12 C11 -5.75(16) . . . . ?
C3 C11 C12 O1 -153.96(11) . . . . ?
C3 C11 C12 N1 30.15(14) . . . . ?

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
C8 H4 O1 0.98 2.58 3.2670(16) 127.5 1_565
C8 H3 N2 0.98 2.61 3.4738(16) 147.8 7_675
N1 H1 O1 0.88 1.99 2.8588(12) 168.7 5_765
C8 H4 O1 0.98 2.58 3.2670(16) 127.5 1_565
C8 H3 N2 0.98 2.61 3.4738(16) 147.8 7_675
N1 H1 O1 0.88 1.99 2.8588(12) 168.7 5_765
N1 H1 O1 0.88 1.99 2.8588(12) 168.7 5_765
C8 H3 N2 0.98 2.61 3.4738(16) 147.8 7_675
C8 H4 O1 0.98 2.58 3.2670(16) 127.5 1_565
N1 H1 O1 0.88 1.99 2.8588(12) 168.7 5_765
C8 H3 N2 0.98 2.61 3.4738(16) 147.8 7_675
C8 H4 O1 0.98 2.58 3.2670(16) 127.5 1_565
N1 H1 O1 0.88 1.99 2.8588(12) 168.7 5_765
C8 H3 N2 0.98 2.61 3.4738(16) 147.8 7_675
C8 H4 O1 0.98 2.58 3.2670(16) 127.5 1_565



# END of CIF
####################################################################### 
# 
# 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_AY_183_1_B
_database_code_depnum_ccdc_archive 'CCDC 1038680'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_date             2014-09-10T12:35:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C52  H44  N8  O4  Cl4'
_chemical_formula_sum            'C52 H44 Cl4 N8 O4'
_chemical_formula_weight         986.75
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.4732(5)
_cell_length_b                   9.5123(4)
_cell_length_c                   19.7950(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.801(2)
_cell_angle_gamma                90
_cell_volume                     2386.95(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_number            51691
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.093
_diffrn_reflns_theta_max         30.6
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_reflns_number_total             14351
_reflns_number_gt                10081
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+1.1244P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         14351
_refine_ls_number_parameters     617
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   0.793
_refine_ls_restrained_S_all      0.793
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 3594 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl4 Cl 1.22686(5) 0.86890(9) 0.95546(5) 0.0403(2) Uani 1 d . .
Cl3 Cl 0.77188(7) 0.63066(10) 0.54851(5) 0.0489(2) Uani 1 d . .
Cl2 Cl 0.72468(7) 0.34780(11) 0.41599(5) 0.0534(3) Uani 1 d . .
O2 O 1.15579(15) 0.4292(2) 0.54035(10) 0.0296(5) Uani 1 d . .
O3 O 0.34086(15) 0.5970(2) 0.46700(10) 0.0300(5) Uani 1 d . .
N5 N 0.37523(17) 0.4304(3) 0.55329(12) 0.0265(5) Uani 1 d . .
H5 H 0.3103 0.4304 0.5509 0.032 Uiso 1 calc . .
Cl1 Cl 0.31219(6) 0.56646(11) 0.08286(5) 0.0481(2) Uani 1 d . .
N3 N 1.12454(17) 0.5985(2) 0.45569(12) 0.0238(5) Uani 1 d . .
H3 H 1.1909 0.6031 0.4621 0.029 Uiso 1 calc . .
O1 O 0.61678(15) 0.6679(2) -0.03710(10) 0.0300(5) Uani 1 d . .
O4 O 0.87149(14) 0.8468(2) 1.03538(10) 0.0286(4) Uani 1 d . .
N1 N 0.66728(17) 0.8359(3) 0.04850(12) 0.0244(5) Uani 1 d . .
H1 H 0.7274 0.8425 0.0424 0.029 Uiso 1 calc . .
C37 C 0.6724(3) 0.8716(4) 0.67671(18) 0.0441(8) Uani 1 d . .
H37 H 0.6881 0.96 0.6977 0.053 Uiso 1 calc . .
C26 C 0.8162(2) 0.3095(3) 0.37378(16) 0.0357(7) Uani 1 d . .
C21 C 0.8928(2) 0.4080(3) 0.37393(15) 0.0267(6) Uani 1 d . .
C20 C 0.9066(2) 0.5451(3) 0.41521(14) 0.0237(6) Uani 1 d . .
H20 H 0.8373 0.5756 0.4157 0.028 Uiso 1 calc . .
C16 C 0.9519(2) 0.6602(3) 0.38167(14) 0.0229(5) Uani 1 d . .
C17 C 1.0567(2) 0.6819(3) 0.40197(14) 0.0229(6) Uani 1 d . .
C18 C 1.1102(2) 0.7857(3) 0.36970(16) 0.0310(7) Uani 1 d . .
H18A H 1.0582 0.8385 0.3332 0.047 Uiso 1 calc . .
H18B H 1.1551 0.7371 0.3487 0.047 Uiso 1 calc . .
H18C H 1.1519 0.8485 0.4063 0.047 Uiso 1 calc . .
C14 C 1.0934(2) 0.5102(3) 0.49864(14) 0.0233(6) Uani 1 d . .
C15 C 0.9799(2) 0.5239(3) 0.49331(15) 0.0247(6) Uani 1 d . .
H15A H 0.9725 0.6032 0.5221 0.03 Uiso 1 calc . .
H15B H 0.9587 0.4398 0.5126 0.03 Uiso 1 calc . .
C27 C 0.4023(2) 0.5120(3) 0.50560(14) 0.0243(6) Uani 1 d . .
C31 C 0.4462(2) 0.3469(3) 0.60582(15) 0.0255(6) Uani 1 d . .
C30 C 0.5506(2) 0.3618(3) 0.61857(14) 0.0247(6) Uani 1 d . .
C33 C 0.6244(2) 0.2854(3) 0.67565(16) 0.0284(6) Uani 1 d . .
N6 N 0.6871(2) 0.2289(3) 0.72183(15) 0.0412(7) Uani 1 d . .
C29 C 0.5934(2) 0.4637(3) 0.57639(14) 0.0225(6) Uani 1 d . .
H29 H 0.6563 0.4217 0.5704 0.027 Uiso 1 calc . .
C34 C 0.6242(2) 0.6042(3) 0.61364(14) 0.0231(6) Uani 1 d . .
C28 C 0.5101(2) 0.4832(3) 0.50159(15) 0.0267(6) Uani 1 d . .
H28A H 0.5307 0.5609 0.4775 0.032 Uiso 1 calc . .
H28B H 0.5072 0.399 0.4733 0.032 Uiso 1 calc . .
C32 C 0.3974(2) 0.2518(3) 0.64560(17) 0.0343(7) Uani 1 d . .
H32A H 0.4518 0.2076 0.6843 0.051 Uiso 1 calc . .
H32B H 0.3565 0.1811 0.6136 0.051 Uiso 1 calc . .
H32C H 0.3524 0.3055 0.6645 0.051 Uiso 1 calc . .
C10 C 0.6544(3) 0.4744(4) 0.20171(18) 0.0404(8) Uani 1 d . .
H10 H 0.7249 0.4549 0.2267 0.048 Uiso 1 calc . .
C9 C 0.6256(2) 0.6045(3) 0.16927(15) 0.0304(6) Uani 1 d . .
H9 H 0.6774 0.6716 0.1734 0.036 Uiso 1 calc . .
C8 C 0.5205(2) 0.6370(3) 0.13053(14) 0.0251(6) Uani 1 d . .
C3 C 0.4907(2) 0.7743(3) 0.08965(14) 0.0243(6) Uani 1 d . .
H3A H 0.4203 0.8021 0.0891 0.029 Uiso 1 calc . .
C4 C 0.5671(2) 0.8922(3) 0.12278(14) 0.0232(6) Uani 1 d . .
N4 N 0.8216(2) 0.7965(3) 0.27659(15) 0.0381(7) Uani 1 d . .
C6 C 0.7333(2) 1.0268(3) 0.13296(16) 0.0282(6) Uani 1 d . .
H6A H 0.7149 1.082 0.1676 0.042 Uiso 1 calc . .
H6B H 0.7387 1.0868 0.0954 0.042 Uiso 1 calc . .
H6C H 0.7999 0.9813 0.156 0.042 Uiso 1 calc . .
C11 C 0.5786(3) 0.3745(4) 0.19686(18) 0.0447(8) Uani 1 d . .
H11 H 0.598 0.2872 0.2185 0.054 Uiso 1 calc . .
C13 C 0.4459(2) 0.5338(3) 0.12811(15) 0.0314(7) Uani 1 d . .
N7 N 0.82126(18) 0.6810(3) 0.94835(12) 0.0265(5) Uani 1 d . .
H7 H 0.7582 0.6816 0.9499 0.032 Uiso 1 calc . .
C44 C 0.8413(2) 0.5965(3) 0.89676(14) 0.0249(6) Uani 1 d . .
C43 C 0.9337(2) 0.6082(3) 0.88550(14) 0.0229(5) Uani 1 d . .
C42 C 1.0182(2) 0.7104(3) 0.92713(14) 0.0212(5) Uani 1 d . .
H42 H 1.087 0.6666 0.9346 0.025 Uiso 1 calc . .
C47 C 1.0146(2) 0.8485(3) 0.88766(14) 0.0219(5) Uani 1 d . .
C48 C 0.9209(2) 0.9057(3) 0.84259(15) 0.0296(6) Uani 1 d . .
H48 H 0.8586 0.8554 0.8339 0.036 Uiso 1 calc . .
C49 C 0.9171(3) 1.0355(3) 0.81007(17) 0.0376(7) Uani 1 d . .
H49 H 0.8528 1.0722 0.7812 0.045 Uiso 1 calc . .
C50 C 1.0089(3) 1.1103(4) 0.82058(17) 0.0379(7) Uani 1 d . .
H50 H 1.0066 1.1968 0.7982 0.045 Uiso 1 calc . .
C51 C 1.1039(2) 1.0567(3) 0.86429(16) 0.0335(7) Uani 1 d . .
H51 H 1.1662 1.1061 0.8712 0.04 Uiso 1 calc . .
C45 C 0.7521(2) 0.5032(3) 0.85553(17) 0.0364(8) Uani 1 d . .
H45A H 0.7724 0.4495 0.8213 0.055 Uiso 1 calc . .
H45B H 0.6916 0.5597 0.8308 0.055 Uiso 1 calc . .
H45C H 0.735 0.4407 0.888 0.055 Uiso 1 calc . .
C40 C 0.8955(2) 0.7630(3) 0.99668(14) 0.0240(6) Uani 1 d . .
C41 C 1.0076(2) 0.7349(3) 1.00104(15) 0.0252(6) Uani 1 d . .
H41A H 1.0336 0.6528 1.0308 0.03 Uiso 1 calc . .
H41B H 1.0512 0.8143 1.0239 0.03 Uiso 1 calc . .
C46 C 0.9529(2) 0.5291(3) 0.82966(15) 0.0274(6) Uani 1 d . .
N8 N 0.9726(2) 0.4704(3) 0.78521(15) 0.0397(7) Uani 1 d . .
N2 N 0.5414(2) 1.0260(3) 0.22862(15) 0.0432(7) Uani 1 d . .
C5 C 0.6504(2) 0.9185(3) 0.10187(14) 0.0225(5) Uani 1 d . .
C1 C 0.5950(2) 0.7458(3) 0.00547(14) 0.0242(6) Uani 1 d . .
C2 C 0.4870(2) 0.7551(3) 0.01142(15) 0.0266(6) Uani 1 d . .
H2A H 0.4481 0.67 -0.0081 0.032 Uiso 1 calc . .
H2B H 0.4495 0.8336 -0.0172 0.032 Uiso 1 calc . .
C7 C 0.5537(2) 0.9684(3) 0.18113(16) 0.0276(6) Uani 1 d . .
C12 C 0.4742(3) 0.4036(4) 0.16006(17) 0.0427(9) Uani 1 d . .
H12 H 0.4228 0.336 0.1567 0.051 Uiso 1 calc . .
C35 C 0.5702(2) 0.6605(3) 0.65611(15) 0.0319(7) Uani 1 d . .
H35 H 0.5171 0.6079 0.6642 0.038 Uiso 1 calc . .
C38 C 0.7286(2) 0.8189(4) 0.63535(19) 0.0414(8) Uani 1 d . .
H38 H 0.7832 0.8709 0.629 0.05 Uiso 1 calc . .
C39 C 0.7030(2) 0.6882(3) 0.60354(16) 0.0298(7) Uani 1 d . .
C36 C 0.5932(3) 0.7918(4) 0.68643(17) 0.0415(8) Uani 1 d . .
H36 H 0.5548 0.8271 0.7138 0.05 Uiso 1 calc . .
C52 C 1.1057(2) 0.9286(3) 0.89778(15) 0.0252(6) Uani 1 d . .
C22 C 0.9612(2) 0.3712(3) 0.33740(16) 0.0341(7) Uani 1 d . .
H22 H 1.0111 0.4363 0.3345 0.041 Uiso 1 calc . .
C24 C 0.8825(3) 0.1451(4) 0.30742(19) 0.0536(11) Uani 1 d . .
H24 H 0.8805 0.0568 0.2868 0.064 Uiso 1 calc . .
C23 C 0.9572(3) 0.2406(4) 0.30526(19) 0.0479(9) Uani 1 d . .
H23 H 1.005 0.2183 0.2824 0.057 Uiso 1 calc . .
C25 C 0.8101(3) 0.1792(4) 0.34019(19) 0.0515(11) Uani 1 d . .
H25 H 0.7575 0.1156 0.3399 0.062 Uiso 1 calc . .
C19 C 0.8812(2) 0.7384(3) 0.32362(16) 0.0265(6) Uani 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
Cl4 C52 1.740(3) . ?
Cl3 C39 1.741(3) . ?
Cl2 C26 1.746(4) . ?
O2 C14 1.230(3) . ?
O3 C27 1.222(3) . ?
N5 C27 1.363(4) . ?
N5 C31 1.398(3) . ?
N5 H5 0.86 . ?
Cl1 C13 1.747(3) . ?
N3 C14 1.359(3) . ?
N3 C17 1.392(3) . ?
N3 H3 0.86 . ?
O1 C1 1.230(3) . ?
O4 C40 1.223(3) . ?
N1 C1 1.359(3) . ?
N1 C5 1.396(3) . ?
N1 H1 0.86 . ?
C37 C36 1.375(5) . ?
C37 C38 1.383(5) . ?
C37 H37 0.93 . ?
C26 C21 1.394(4) . ?
C26 C25 1.396(5) . ?
C21 C22 1.394(4) . ?
C21 C20 1.516(4) . ?
C20 C16 1.513(4) . ?
C20 C15 1.540(4) . ?
C20 H20 0.98 . ?
C16 C17 1.346(4) . ?
C16 C19 1.428(4) . ?
C17 C18 1.489(4) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C14 C15 1.502(4) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C27 C28 1.507(4) . ?
C31 C30 1.349(4) . ?
C31 C32 1.490(4) . ?
C30 C33 1.426(4) . ?
C30 C29 1.515(4) . ?
C33 N6 1.147(4) . ?
C29 C34 1.515(4) . ?
C29 C28 1.536(4) . ?
C29 H29 0.98 . ?
C34 C35 1.392(4) . ?
C34 C39 1.395(4) . ?
C28 H28A 0.97 . ?
C28 H28B 0.97 . ?
C32 H32A 0.96 . ?
C32 H32B 0.96 . ?
C32 H32C 0.96 . ?
C10 C11 1.374(5) . ?
C10 C9 1.387(4) . ?
C10 H10 0.93 . ?
C9 C8 1.397(4) . ?
C9 H9 0.93 . ?
C8 C13 1.394(4) . ?
C8 C3 1.517(4) . ?
C3 C4 1.514(4) . ?
C3 C2 1.543(4) . ?
C3 H3A 0.98 . ?
C4 C5 1.345(4) . ?
C4 C7 1.426(4) . ?
N4 C19 1.145(4) . ?
C6 C5 1.491(4) . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
C11 C12 1.376(5) . ?
C11 H11 0.93 . ?
C13 C12 1.384(5) . ?
N7 C40 1.369(4) . ?
N7 C44 1.396(3) . ?
N7 H7 0.86 . ?
C44 C43 1.342(4) . ?
C44 C45 1.494(4) . ?
C43 C46 1.431(4) . ?
C43 C42 1.512(4) . ?
C42 C47 1.521(4) . ?
C42 C41 1.535(4) . ?
C42 H42 0.98 . ?
C47 C48 1.387(4) . ?
C47 C52 1.400(4) . ?
C48 C49 1.386(4) . ?
C48 H48 0.93 . ?
C49 C50 1.379(5) . ?
C49 H49 0.93 . ?
C50 C51 1.378(5) . ?
C50 H50 0.93 . ?
C51 C52 1.384(4) . ?
C51 H51 0.93 . ?
C45 H45A 0.96 . ?
C45 H45B 0.96 . ?
C45 H45C 0.96 . ?
C40 C41 1.507(4) . ?
C41 H41A 0.97 . ?
C41 H41B 0.97 . ?
C46 N8 1.147(4) . ?
N2 C7 1.148(4) . ?
C1 C2 1.502(4) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C12 H12 0.93 . ?
C35 C36 1.375(5) . ?
C35 H35 0.93 . ?
C38 C39 1.384(4) . ?
C38 H38 0.93 . ?
C36 H36 0.93 . ?
C22 C23 1.388(4) . ?
C22 H22 0.93 . ?
C24 C23 1.367(6) . ?
C24 C25 1.381(6) . ?
C24 H24 0.93 . ?
C23 H23 0.93 . ?
C25 H25 0.93 . ?

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
C27 N5 C31 124.2(2) . . ?
C27 N5 H5 117.9 . . ?
C31 N5 H5 117.9 . . ?
C14 N3 C17 124.6(2) . . ?
C14 N3 H3 117.7 . . ?
C17 N3 H3 117.7 . . ?
C1 N1 C5 124.3(2) . . ?
C1 N1 H1 117.8 . . ?
C5 N1 H1 117.8 . . ?
C36 C37 C38 119.3(3) . . ?
C36 C37 H37 120.4 . . ?
C38 C37 H37 120.4 . . ?
C21 C26 C25 121.5(3) . . ?
C21 C26 Cl2 120.1(3) . . ?
C25 C26 Cl2 118.4(3) . . ?
C26 C21 C22 116.7(3) . . ?
C26 C21 C20 122.3(3) . . ?
C22 C21 C20 120.9(3) . . ?
C16 C20 C21 112.3(2) . . ?
C16 C20 C15 108.5(2) . . ?
C21 C20 C15 110.4(2) . . ?
C16 C20 H20 108.5 . . ?
C21 C20 H20 108.5 . . ?
C15 C20 H20 108.5 . . ?
C17 C16 C19 120.4(3) . . ?
C17 C16 C20 121.3(2) . . ?
C19 C16 C20 118.1(2) . . ?
C16 C17 N3 119.4(2) . . ?
C16 C17 C18 125.8(3) . . ?
N3 C17 C18 114.7(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C14 N3 121.4(2) . . ?
O2 C14 C15 123.3(3) . . ?
N3 C14 C15 115.2(2) . . ?
C14 C15 C20 111.9(2) . . ?
C14 C15 H15A 109.2 . . ?
C20 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C20 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
O3 C27 N5 121.8(2) . . ?
O3 C27 C28 123.2(3) . . ?
N5 C27 C28 114.9(2) . . ?
C30 C31 N5 119.1(2) . . ?
C30 C31 C32 125.7(3) . . ?
N5 C31 C32 115.1(2) . . ?
C31 C30 C33 119.9(3) . . ?
C31 C30 C29 122.1(2) . . ?
C33 C30 C29 118.0(2) . . ?
N6 C33 C30 176.8(3) . . ?
C30 C29 C34 112.9(2) . . ?
C30 C29 C28 108.6(2) . . ?
C34 C29 C28 110.6(2) . . ?
C30 C29 H29 108.2 . . ?
C34 C29 H29 108.2 . . ?
C28 C29 H29 108.2 . . ?
C35 C34 C39 116.5(3) . . ?
C35 C34 C29 121.3(2) . . ?
C39 C34 C29 122.1(2) . . ?
C27 C28 C29 112.0(2) . . ?
C27 C28 H28A 109.2 . . ?
C29 C28 H28A 109.2 . . ?
C27 C28 H28B 109.2 . . ?
C29 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120 . . ?
C9 C10 H10 120 . . ?
C10 C9 C8 121.6(3) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C13 C8 C9 116.6(3) . . ?
C13 C8 C3 122.0(3) . . ?
C9 C8 C3 121.3(3) . . ?
C4 C3 C8 112.9(2) . . ?
C4 C3 C2 108.0(2) . . ?
C8 C3 C2 110.2(2) . . ?
C4 C3 H3A 108.6 . . ?
C8 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C5 C4 C7 120.2(3) . . ?
C5 C4 C3 121.4(2) . . ?
C7 C4 C3 118.3(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 120 . . ?
C12 C11 H11 120 . . ?
C12 C13 C8 122.1(3) . . ?
C12 C13 Cl1 118.0(2) . . ?
C8 C13 Cl1 119.9(3) . . ?
C40 N7 C44 124.2(2) . . ?
C40 N7 H7 117.9 . . ?
C44 N7 H7 117.9 . . ?
C43 C44 N7 119.6(2) . . ?
C43 C44 C45 125.3(3) . . ?
N7 C44 C45 115.0(2) . . ?
C44 C43 C46 120.3(3) . . ?
C44 C43 C42 122.2(2) . . ?
C46 C43 C42 117.3(2) . . ?
C43 C42 C47 112.9(2) . . ?
C43 C42 C41 108.7(2) . . ?
C47 C42 C41 111.2(2) . . ?
C43 C42 H42 108 . . ?
C47 C42 H42 108 . . ?
C41 C42 H42 108 . . ?
C48 C47 C52 116.2(3) . . ?
C48 C47 C42 122.2(2) . . ?
C52 C47 C42 121.5(2) . . ?
C49 C48 C47 122.0(3) . . ?
C49 C48 H48 119 . . ?
C47 C48 H48 119 . . ?
C50 C49 C48 120.0(3) . . ?
C50 C49 H49 120 . . ?
C48 C49 H49 120 . . ?
C51 C50 C49 119.9(3) . . ?
C51 C50 H50 120 . . ?
C49 C50 H50 120 . . ?
C50 C51 C52 119.2(3) . . ?
C50 C51 H51 120.4 . . ?
C52 C51 H51 120.4 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O4 C40 N7 121.6(2) . . ?
O4 C40 C41 123.5(3) . . ?
N7 C40 C41 114.8(2) . . ?
C40 C41 C42 112.8(2) . . ?
C40 C41 H41A 109 . . ?
C42 C41 H41A 109 . . ?
C40 C41 H41B 109 . . ?
C42 C41 H41B 109 . . ?
H41A C41 H41B 107.8 . . ?
N8 C46 C43 176.4(3) . . ?
C4 C5 N1 119.7(2) . . ?
C4 C5 C6 126.1(3) . . ?
N1 C5 C6 114.2(2) . . ?
O1 C1 N1 121.6(2) . . ?
O1 C1 C2 123.4(3) . . ?
N1 C1 C2 114.9(2) . . ?
C1 C2 C3 112.5(2) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N2 C7 C4 177.8(3) . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C36 C35 C34 121.7(3) . . ?
C36 C35 H35 119.2 . . ?
C34 C35 H35 119.2 . . ?
C37 C38 C39 119.5(3) . . ?
C37 C38 H38 120.2 . . ?
C39 C38 H38 120.2 . . ?
C38 C39 C34 122.2(3) . . ?
C38 C39 Cl3 117.6(2) . . ?
C34 C39 Cl3 120.2(2) . . ?
C37 C36 C35 120.8(3) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C51 C52 C47 122.6(3) . . ?
C51 C52 Cl4 117.5(2) . . ?
C47 C52 Cl4 119.9(2) . . ?
C23 C22 C21 122.2(3) . . ?
C23 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C23 C24 C25 120.2(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C23 C22 119.7(4) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C24 C25 C26 119.7(3) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
N4 C19 C16 177.2(3) . . ?

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
C25 C26 C21 C22 1.5(4) . . . . ?
Cl2 C26 C21 C22 -178.3(2) . . . . ?
C25 C26 C21 C20 -174.9(3) . . . . ?
Cl2 C26 C21 C20 5.3(4) . . . . ?
C26 C21 C20 C16 -152.3(3) . . . . ?
C22 C21 C20 C16 31.5(3) . . . . ?
C26 C21 C20 C15 86.5(3) . . . . ?
C22 C21 C20 C15 -89.8(3) . . . . ?
C21 C20 C16 C17 -91.5(3) . . . . ?
C15 C20 C16 C17 30.9(3) . . . . ?
C21 C20 C16 C19 83.6(3) . . . . ?
C15 C20 C16 C19 -154.1(2) . . . . ?
C19 C16 C17 N3 -176.0(2) . . . . ?
C20 C16 C17 N3 -1.1(4) . . . . ?
C19 C16 C17 C18 1.1(4) . . . . ?
C20 C16 C17 C18 176.0(3) . . . . ?
C14 N3 C17 C16 -11.6(4) . . . . ?
C14 N3 C17 C18 171.0(3) . . . . ?
C17 N3 C14 O2 172.8(3) . . . . ?
C17 N3 C14 C15 -9.6(4) . . . . ?
O2 C14 C15 C20 -142.0(3) . . . . ?
N3 C14 C15 C20 40.4(3) . . . . ?
C16 C20 C15 C14 -48.9(3) . . . . ?
C21 C20 C15 C14 74.6(3) . . . . ?
C31 N5 C27 O3 -170.2(3) . . . . ?
C31 N5 C27 C28 13.0(4) . . . . ?
C27 N5 C31 C30 10.6(4) . . . . ?
C27 N5 C31 C32 -172.1(3) . . . . ?
N5 C31 C30 C33 175.2(3) . . . . ?
C32 C31 C30 C33 -1.8(5) . . . . ?
N5 C31 C30 C29 -1.6(4) . . . . ?
C32 C31 C30 C29 -178.6(3) . . . . ?
C31 C30 C29 C34 95.4(3) . . . . ?
C33 C30 C29 C34 -81.5(3) . . . . ?
C31 C30 C29 C28 -27.6(4) . . . . ?
C33 C30 C29 C28 155.5(3) . . . . ?
C30 C29 C34 C35 -32.5(3) . . . . ?
C28 C29 C34 C35 89.4(3) . . . . ?
C30 C29 C34 C39 151.9(2) . . . . ?
C28 C29 C34 C39 -86.3(3) . . . . ?
O3 C27 C28 C29 140.2(3) . . . . ?
N5 C27 C28 C29 -43.1(3) . . . . ?
C30 C29 C28 C27 48.2(3) . . . . ?
C34 C29 C28 C27 -76.2(3) . . . . ?
C11 C10 C9 C8 -0.7(5) . . . . ?
C10 C9 C8 C13 2.0(4) . . . . ?
C10 C9 C8 C3 -174.4(3) . . . . ?
C13 C8 C3 C4 154.9(3) . . . . ?
C9 C8 C3 C4 -28.9(4) . . . . ?
C13 C8 C3 C2 -84.3(3) . . . . ?
C9 C8 C3 C2 91.9(3) . . . . ?
C8 C3 C4 C5 91.8(3) . . . . ?
C2 C3 C4 C5 -30.3(3) . . . . ?
C8 C3 C4 C7 -83.3(3) . . . . ?
C2 C3 C4 C7 154.6(2) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C9 C8 C13 C12 -2.3(4) . . . . ?
C3 C8 C13 C12 174.1(3) . . . . ?
C9 C8 C13 Cl1 178.4(2) . . . . ?
C3 C8 C13 Cl1 -5.2(4) . . . . ?
C40 N7 C44 C43 -9.8(4) . . . . ?
C40 N7 C44 C45 173.1(3) . . . . ?
N7 C44 C43 C46 -175.9(3) . . . . ?
C45 C44 C43 C46 0.9(4) . . . . ?
N7 C44 C43 C42 0.1(4) . . . . ?
C45 C44 C43 C42 176.9(3) . . . . ?
C44 C43 C42 C47 -95.9(3) . . . . ?
C46 C43 C42 C47 80.2(3) . . . . ?
C44 C43 C42 C41 27.9(4) . . . . ?
C46 C43 C42 C41 -155.9(2) . . . . ?
C43 C42 C47 C48 32.4(4) . . . . ?
C41 C42 C47 C48 -90.1(3) . . . . ?
C43 C42 C47 C52 -151.0(2) . . . . ?
C41 C42 C47 C52 86.5(3) . . . . ?
C52 C47 C48 C49 -0.8(4) . . . . ?
C42 C47 C48 C49 176.1(3) . . . . ?
C47 C48 C49 C50 1.7(5) . . . . ?
C48 C49 C50 C51 -1.0(5) . . . . ?
C49 C50 C51 C52 -0.7(5) . . . . ?
C44 N7 C40 O4 171.7(3) . . . . ?
C44 N7 C40 C41 -11.8(4) . . . . ?
O4 C40 C41 C42 -142.8(3) . . . . ?
N7 C40 C41 C42 40.8(3) . . . . ?
C43 C42 C41 C40 -46.9(3) . . . . ?
C47 C42 C41 C40 78.0(3) . . . . ?
C7 C4 C5 N1 175.0(2) . . . . ?
C3 C4 C5 N1 0.0(4) . . . . ?
C7 C4 C5 C6 -1.9(4) . . . . ?
C3 C4 C5 C6 -176.9(3) . . . . ?
C1 N1 C5 C4 13.0(4) . . . . ?
C1 N1 C5 C6 -169.7(3) . . . . ?
C5 N1 C1 O1 -174.5(3) . . . . ?
C5 N1 C1 C2 8.6(4) . . . . ?
O1 C1 C2 C3 142.8(3) . . . . ?
N1 C1 C2 C3 -40.4(3) . . . . ?
C4 C3 C2 C1 49.1(3) . . . . ?
C8 C3 C2 C1 -74.6(3) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C8 C13 C12 C11 1.4(5) . . . . ?
Cl1 C13 C12 C11 -179.3(3) . . . . ?
C39 C34 C35 C36 0.0(4) . . . . ?
C29 C34 C35 C36 -175.8(3) . . . . ?
C36 C37 C38 C39 1.1(5) . . . . ?
C37 C38 C39 C34 -2.3(5) . . . . ?
C37 C38 C39 Cl3 176.9(2) . . . . ?
C35 C34 C39 C38 1.7(4) . . . . ?
C29 C34 C39 C38 177.5(3) . . . . ?
C35 C34 C39 Cl3 -177.5(2) . . . . ?
C29 C34 C39 Cl3 -1.7(4) . . . . ?
C38 C37 C36 C35 0.6(5) . . . . ?
C34 C35 C36 C37 -1.2(5) . . . . ?
C50 C51 C52 C47 1.7(4) . . . . ?
C50 C51 C52 Cl4 -177.3(2) . . . . ?
C48 C47 C52 C51 -1.0(4) . . . . ?
C42 C47 C52 C51 -177.8(3) . . . . ?
C48 C47 C52 Cl4 178.0(2) . . . . ?
C42 C47 C52 Cl4 1.2(4) . . . . ?
C26 C21 C22 C23 -3.1(4) . . . . ?
C20 C21 C22 C23 173.4(3) . . . . ?
C25 C24 C23 C22 1.3(5) . . . . ?
C21 C22 C23 C24 1.7(5) . . . . ?
C23 C24 C25 C26 -2.7(5) . . . . ?
C21 C26 C25 C24 1.3(5) . . . . ?
Cl2 C26 C25 C24 -178.9(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
C2 H2B Cl4 0.97 2.88 3.472(3) 120.2 1_454
N7 H7 O1 0.86 2.01 2.868(3) 173.5 1_556
C6 H6B Cl4 0.96 2.96 3.818(3) 149.9 2_756
C15 H15A Cl3 0.97 2.93 3.486(3) 117.2 .
C18 H18C Cl3 0.96 2.9 3.764(3) 149.6 2_756
C18 H18A N8 0.96 2.57 3.379(4) 142.6 2_756
N1 H1 O4 0.86 1.99 2.852(3) 175.2 1_554
N3 H3 O3 0.86 1.99 2.847(3) 172.9 1_655
N5 H5 O2 0.86 2.02 2.880(3) 177.4 1_455
C2 H2B Cl4 0.97 2.88 3.472(3) 120.2 1_454
N7 H7 O1 0.86 2.01 2.868(3) 173.5 1_556
C6 H6B Cl4 0.96 2.96 3.818(3) 149.9 2_756
C15 H15A Cl3 0.97 2.93 3.486(3) 117.2 .
C18 H18C Cl3 0.96 2.9 3.764(3) 149.6 2_756
C18 H18A N8 0.96 2.57 3.379(4) 142.6 2_756
N1 H1 O4 0.86 1.99 2.852(3) 175.2 1_554
N3 H3 O3 0.86 1.99 2.847(3) 172.9 1_655
N5 H5 O2 0.86 2.02 2.880(3) 177.4 1_455
N5 H5 O2 0.86 2.02 2.880(3) 177.4 1_455
N1 H1 O4 0.86 1.99 2.852(3) 175.2 1_554
C15 H15A Cl3 0.97 2.93 3.486(3) 117.2 .
N5 H5 O2 0.86 2.02 2.880(3) 177.4 1_455
N3 H3 O3 0.86 1.99 2.847(3) 172.9 1_655
N1 H1 O4 0.86 1.99 2.852(3) 175.2 1_554
C18 H18A N8 0.96 2.57 3.379(4) 142.6 2_756
C18 H18C Cl3 0.96 2.9 3.764(3) 149.6 2_756
C15 H15A Cl3 0.97 2.93 3.486(3) 117.2 .
C6 H6B Cl4 0.96 2.96 3.818(3) 149.9 2_756
N7 H7 O1 0.86 2.01 2.868(3) 173.5 1_556
C2 H2B Cl4 0.97 2.88 3.472(3) 120.2 1_454



# END of CIF
####################################################################### 
# 
# 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_AY_4_SMe
_database_code_depnum_ccdc_archive 'CCDC 1057417'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_date             2014-12-16T14:52:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14  H14  N2  O1  S1'
_chemical_formula_sum            'C14 H14 N2 O S'
_chemical_formula_weight         258.33

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.924(5)
_cell_length_b                   5.7267(11)
_cell_length_c                   23.879(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.393(7)
_cell_angle_gamma                90
_cell_volume                     2645.6(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       char
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_number            33413
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.208
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.956
_reflns_number_total             2397
_reflns_number_gt                1812
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0672P)²+3.2091P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2397
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.05
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.127
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   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'
S S 0.1246 0.1234 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.27449(4) 0.46531(15) 0.16493(3) 0.0674(3) Uani 1 d . .
O002 O 0.69666(9) 0.9133(4) 0.43443(9) 0.0653(6) Uani 1 d . .
N1 N 0.66353(10) 0.6079(4) 0.47584(9) 0.0502(5) Uani 1 d . .
H1 H 0.7047 0.6034 0.5052 0.06 Uiso 1 calc . .
N2 N 0.45521(12) 0.1916(4) 0.44483(11) 0.0640(7) Uani 1 d . .
C5 C 0.61455(12) 0.4461(4) 0.47752(10) 0.0427(6) Uani 1 d . .
C7 C 0.49799(12) 0.3092(4) 0.44246(11) 0.0459(6) Uani 1 d . .
C4 C 0.54900(11) 0.4625(4) 0.43801(10) 0.0438(6) Uani 1 d . .
C11 C 0.34524(12) 0.5323(5) 0.23197(11) 0.0461(6) Uani 1 d . .
C8 C 0.46083(12) 0.6180(5) 0.33846(11) 0.0482(6) Uani 1 d . .
C1 C 0.65216(12) 0.7715(5) 0.43220(11) 0.0498(6) Uani 1 d . .
C10 C 0.35061(14) 0.7303(5) 0.26598(13) 0.0599(7) Uani 1 d . .
H10 H 0.3143 0.8421 0.253 0.072 Uiso 1 calc . .
C13 C 0.45712(13) 0.4203(5) 0.30483(12) 0.0585(7) Uani 1 d . .
H13 H 0.4945 0.3126 0.3177 0.07 Uiso 1 calc . .
C2 C 0.58338(12) 0.7589(5) 0.38021(12) 0.0546(7) Uani 1 d . .
H2A H 0.588 0.6556 0.3487 0.066 Uiso 1 calc . .
H2B H 0.5715 0.9168 0.3624 0.066 Uiso 1 calc . .
C12 C 0.39901(14) 0.3737(5) 0.25155(12) 0.0572(7) Uani 1 d . .
H12 H 0.3969 0.2344 0.2293 0.069 Uiso 1 calc . .
C3 C 0.52415(12) 0.6708(5) 0.39591(12) 0.0514(6) Uani 1 d . .
H3 H 0.5112 0.7974 0.4185 0.062 Uiso 1 calc . .
C9 C 0.40729(14) 0.7708(5) 0.31851(13) 0.0604(7) Uani 1 d . .
H9 H 0.4089 0.9084 0.3412 0.072 Uiso 1 calc . .
C6 C 0.64100(14) 0.2733(5) 0.52690(13) 0.0623(8) Uani 1 d . .
H6A H 0.653 0.3524 0.566 0.093 Uiso 1 calc . .
H6B H 0.6822 0.1973 0.5252 0.093 Uiso 1 calc . .
H6C H 0.6053 0.1556 0.5223 0.093 Uiso 1 calc . .
C14 C 0.21966(15) 0.7137(7) 0.15327(15) 0.0825(10) Uani 1 d . .
H14A H 0.2054 0.7311 0.1877 0.124 Uiso 1 calc . .
H14B H 0.1787 0.6928 0.116 0.124 Uiso 1 calc . .
H14C H 0.2447 0.8538 0.1497 0.124 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
S1 C11 1.759(2) . ?
S1 C14 1.782(4) . ?
O002 C1 1.221(3) . ?
N1 C1 1.353(3) . ?
N1 C5 1.394(3) . ?
N1 H1 0.88 . ?
N2 C7 1.139(3) . ?
C5 C4 1.339(3) . ?
C5 C6 1.476(4) . ?
C7 C4 1.417(3) . ?
C4 C3 1.518(4) . ?
C11 C10 1.374(4) . ?
C11 C12 1.382(4) . ?
C8 C9 1.357(4) . ?
C8 C13 1.373(4) . ?
C8 C3 1.531(3) . ?
C1 C2 1.502(3) . ?
C10 C9 1.379(4) . ?
C10 H10 0.95 . ?
C13 C12 1.411(4) . ?
C13 H13 0.95 . ?
C2 C3 1.512(3) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C12 H12 0.95 . ?
C3 H3 1 . ?
C9 H9 0.95 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 S1 C14 103.69(14) . . ?
C1 N1 C5 124.54(19) . . ?
C1 N1 H1 117.7 . . ?
C5 N1 H1 117.7 . . ?
C4 C5 N1 120.0(2) . . ?
C4 C5 C6 125.6(2) . . ?
N1 C5 C6 114.4(2) . . ?
N2 C7 C4 177.5(3) . . ?
C5 C4 C7 120.1(2) . . ?
C5 C4 C3 121.5(2) . . ?
C7 C4 C3 117.3(2) . . ?
C10 C11 C12 118.0(2) . . ?
C10 C11 S1 124.7(2) . . ?
C12 C11 S1 117.3(2) . . ?
C9 C8 C13 118.1(2) . . ?
C9 C8 C3 120.3(2) . . ?
C13 C8 C3 121.6(2) . . ?
O002 C1 N1 121.3(2) . . ?
O002 C1 C2 122.8(2) . . ?
N1 C1 C2 115.8(2) . . ?
C11 C10 C9 121.7(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C8 C13 C12 121.4(2) . . ?
C8 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C1 C2 C3 115.4(2) . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
C3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C11 C12 C13 119.5(3) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C2 C3 C4 108.7(2) . . ?
C2 C3 C8 110.8(2) . . ?
C4 C3 C8 113.5(2) . . ?
C2 C3 H3 107.9 . . ?
C4 C3 H3 107.9 . . ?
C8 C3 H3 107.9 . . ?
C8 C9 C10 121.3(3) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?



# END of CIF
####################################################################### 
# 
# 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_AY_Ferrocene
_database_code_depnum_ccdc_archive 'CCDC 1057418'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_date             2015-01-06T20:00:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17  H15  N3  Fe1'
_chemical_formula_sum            'C17 H15 Fe N3'
_chemical_formula_weight         317.17

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   35.793(4)
_cell_length_b                   5.7087(6)
_cell_length_c                   13.3460(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.709(4)
_cell_angle_gamma                90
_cell_volume                     2688.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.117
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.1157
_diffrn_reflns_number            17590
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.097
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.981
_reflns_number_total             2597
_reflns_number_gt                1941
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0993P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2597
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.166
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.168
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.151
_refine_diff_density_min         -1.388
_refine_diff_density_rms         0.279

#----------------------------------------------------------------------------#
#                   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'
Fe Fe 0.3463 0.8444 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.43025(2) 0.77238(9) 0.41555(4) 0.0097(2) Uani 1 d . .
N1 N 0.27941(9) 0.4986(5) 0.4625(3) 0.0129(8) Uani 1 d . .
N2 N 0.29899(10) 0.2144(5) 0.5814(3) 0.0181(9) Uani 1 d . .
H2A H 0.2757 0.1596 0.57 0.022 Uiso 1 calc . .
H2B H 0.3164 0.1456 0.6263 0.022 Uiso 1 calc . .
N3 N 0.33261(10) 1.1255(7) 0.2981(3) 0.0253(10) Uani 1 d . .
C9 C 0.42571(11) 0.6574(7) 0.5587(3) 0.0120(9) Uani 1 d . .
H9 H 0.426 0.4988 0.5803 0.014 Uiso 1 calc . .
C8 C 0.39254(11) 0.7882(6) 0.5147(3) 0.0106(8) Uani 1 d . .
C16 C 0.45274(12) 0.8550(7) 0.2871(3) 0.0150(9) Uani 1 d . .
H16 H 0.4676 0.9885 0.2779 0.018 Uiso 1 calc . .
C3 C 0.35377(11) 0.6920(6) 0.4947(3) 0.0112(8) Uani 1 d . .
C10 C 0.45769(12) 0.8046(7) 0.5642(3) 0.0143(9) Uani 1 d . .
H10 H 0.4831 0.7621 0.5904 0.017 Uiso 1 calc . .
C2 C 0.32399(11) 0.7874(6) 0.4210(3) 0.0122(9) Uani 1 d . .
C5 C 0.30804(11) 0.4034(7) 0.5304(3) 0.0126(9) Uani 1 d . .
C11 C 0.44533(11) 1.0276(7) 0.5238(3) 0.0138(9) Uani 1 d . .
H11 H 0.4611 1.1592 0.518 0.017 Uiso 1 calc . .
C13 C 0.40148(13) 0.6105(7) 0.2898(3) 0.0193(10) Uani 1 d . .
H13 H 0.3763 0.5529 0.283 0.023 Uiso 1 calc . .
C12 C 0.40540(11) 1.0188(6) 0.4936(3) 0.0124(9) Uani 1 d . .
H12 H 0.3898 1.1441 0.4644 0.015 Uiso 1 calc . .
C4 C 0.34504(11) 0.5002(6) 0.5481(3) 0.0129(9) Uani 1 d . .
H4 H 0.364 0.4313 0.5976 0.015 Uiso 1 calc . .
C7 C 0.32946(11) 0.9773(7) 0.3553(3) 0.0164(10) Uani 1 d . .
C15 C 0.46673(12) 0.6333(7) 0.3269(3) 0.0175(9) Uani 1 d . .
H15 H 0.4926 0.5934 0.3489 0.021 Uiso 1 calc . .
C17 C 0.41251(12) 0.8401(8) 0.2640(3) 0.0176(9) Uani 1 d . .
H17 H 0.3959 0.962 0.2361 0.021 Uiso 1 calc . .
C6 C 0.25573(11) 0.7913(7) 0.3360(3) 0.0149(9) Uani 1 d . .
H6A H 0.2323 0.7057 0.3396 0.022 Uiso 1 calc . .
H6B H 0.2615 0.7805 0.2669 0.022 Uiso 1 calc . .
H6C H 0.2526 0.9561 0.3533 0.022 Uiso 1 calc . .
C1 C 0.28764(11) 0.6864(7) 0.4095(3) 0.0124(9) Uani 1 d . .
C14 C 0.43519(13) 0.4835(7) 0.3277(3) 0.0192(10) Uani 1 d . .
H14 H 0.4363 0.325 0.3498 0.023 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
Fe1 C13 2.036(4) . ?
Fe1 C12 2.041(4) . ?
Fe1 C8 2.045(5) . ?
Fe1 C14 2.048(4) . ?
Fe1 C9 2.052(4) . ?
Fe1 C11 2.058(4) . ?
Fe1 C15 2.063(5) . ?
Fe1 C16 2.067(4) . ?
Fe1 C10 2.068(4) . ?
N1 C1 1.344(5) . ?
N1 C5 1.361(5) . ?
N2 C5 1.344(5) . ?
N2 H2A 0.88 . ?
N2 H2B 0.88 . ?
N3 C7 1.158(6) . ?
C9 C10 1.412(6) . ?
C9 C8 1.441(5) . ?
C9 H9 0.95 . ?
C8 C12 1.438(5) . ?
C8 C3 1.474(5) . ?
C16 C17 1.423(6) . ?
C16 C15 1.430(6) . ?
C16 H16 0.95 . ?
C3 C4 1.371(6) . ?
C3 C2 1.431(5) . ?
C10 C11 1.424(5) . ?
C10 H10 0.95 . ?
C2 C1 1.408(6) . ?
C2 C7 1.428(6) . ?
C5 C4 1.418(5) . ?
C11 C12 1.419(5) . ?
C11 H11 0.95 . ?
C13 C14 1.425(6) . ?
C13 C17 1.428(6) . ?
C13 H13 0.95 . ?
C12 H12 0.95 . ?
C4 H4 0.95 . ?
C15 C14 1.418(6) . ?
C15 H15 0.95 . ?
C17 H17 0.95 . ?
C6 C1 1.499(5) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C14 H14 0.95 . ?

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
C13 Fe1 C12 121.99(17) . . ?
C13 Fe1 C8 104.82(17) . . ?
C12 Fe1 C8 41.21(15) . . ?
C13 Fe1 C14 40.84(17) . . ?
C12 Fe1 C14 159.06(17) . . ?
C8 Fe1 C14 122.41(17) . . ?
C13 Fe1 C9 120.89(17) . . ?
C12 Fe1 C9 68.65(16) . . ?
C8 Fe1 C9 41.19(15) . . ?
C14 Fe1 C9 107.65(16) . . ?
C13 Fe1 C11 159.34(16) . . ?
C12 Fe1 C11 40.50(15) . . ?
C8 Fe1 C11 68.81(16) . . ?
C14 Fe1 C11 159.03(16) . . ?
C9 Fe1 C11 68.03(16) . . ?
C13 Fe1 C15 68.52(18) . . ?
C12 Fe1 C15 158.46(17) . . ?
C8 Fe1 C15 159.81(16) . . ?
C14 Fe1 C15 40.33(17) . . ?
C9 Fe1 C15 124.60(16) . . ?
C11 Fe1 C15 123.94(17) . . ?
C13 Fe1 C16 68.53(18) . . ?
C12 Fe1 C16 121.99(16) . . ?
C8 Fe1 C16 156.64(16) . . ?
C14 Fe1 C16 68.03(17) . . ?
C9 Fe1 C16 161.40(16) . . ?
C11 Fe1 C16 109.11(17) . . ?
C15 Fe1 C16 40.51(16) . . ?
C13 Fe1 C10 157.38(16) . . ?
C12 Fe1 C10 68.08(16) . . ?
C8 Fe1 C10 68.54(16) . . ?
C14 Fe1 C10 123.21(16) . . ?
C9 Fe1 C10 40.08(16) . . ?
C11 Fe1 C10 40.37(15) . . ?
C15 Fe1 C10 109.89(17) . . ?
C16 Fe1 C10 125.92(17) . . ?
C1 N1 C5 117.5(3) . . ?
C5 N2 H2A 120 . . ?
C5 N2 H2B 120 . . ?
H2A N2 H2B 120 . . ?
C10 C9 C8 108.5(3) . . ?
C10 C9 Fe1 70.6(2) . . ?
C8 C9 Fe1 69.2(2) . . ?
C10 C9 H9 125.7 . . ?
C8 C9 H9 125.7 . . ?
Fe1 C9 H9 126.1 . . ?
C12 C8 C9 106.6(3) . . ?
C12 C8 C3 128.9(3) . . ?
C9 C8 C3 124.5(3) . . ?
C12 C8 Fe1 69.2(2) . . ?
C9 C8 Fe1 69.7(2) . . ?
C3 C8 Fe1 124.8(3) . . ?
C17 C16 C15 107.8(4) . . ?
C17 C16 Fe1 69.2(2) . . ?
C15 C16 Fe1 69.6(2) . . ?
C17 C16 H16 126.1 . . ?
C15 C16 H16 126.1 . . ?
Fe1 C16 H16 126.6 . . ?
C4 C3 C2 116.9(4) . . ?
C4 C3 C8 119.6(3) . . ?
C2 C3 C8 123.5(4) . . ?
C9 C10 C11 108.4(3) . . ?
C9 C10 Fe1 69.3(2) . . ?
C11 C10 Fe1 69.4(2) . . ?
C9 C10 H10 125.8 . . ?
C11 C10 H10 125.8 . . ?
Fe1 C10 H10 127 . . ?
C1 C2 C7 117.6(3) . . ?
C1 C2 C3 119.2(4) . . ?
C7 C2 C3 123.2(4) . . ?
N2 C5 N1 116.0(3) . . ?
N2 C5 C4 121.8(3) . . ?
N1 C5 C4 122.2(4) . . ?
C12 C11 C10 108.0(3) . . ?
C12 C11 Fe1 69.1(2) . . ?
C10 C11 Fe1 70.2(2) . . ?
C12 C11 H11 126 . . ?
C10 C11 H11 126 . . ?
Fe1 C11 H11 126.3 . . ?
C14 C13 C17 107.5(4) . . ?
C14 C13 Fe1 70.0(2) . . ?
C17 C13 Fe1 70.2(2) . . ?
C14 C13 H13 126.3 . . ?
C17 C13 H13 126.3 . . ?
Fe1 C13 H13 125.2 . . ?
C11 C12 C8 108.5(3) . . ?
C11 C12 Fe1 70.4(2) . . ?
C8 C12 Fe1 69.5(2) . . ?
C11 C12 H12 125.8 . . ?
C8 C12 H12 125.8 . . ?
Fe1 C12 H12 125.9 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
N3 C7 C2 176.5(4) . . ?
C14 C15 C16 107.9(4) . . ?
C14 C15 Fe1 69.3(3) . . ?
C16 C15 Fe1 69.9(2) . . ?
C14 C15 H15 126 . . ?
C16 C15 H15 126 . . ?
Fe1 C15 H15 126.4 . . ?
C16 C17 C13 108.2(4) . . ?
C16 C17 H17 125.9 . . ?
C13 C17 H17 125.9 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C1 C2 123.3(3) . . ?
N1 C1 C6 116.9(3) . . ?
C2 C1 C6 119.8(4) . . ?
C15 C14 C13 108.5(4) . . ?
C15 C14 Fe1 70.4(2) . . ?
C13 C14 Fe1 69.1(2) . . ?
C15 C14 H14 125.7 . . ?
C13 C14 H14 125.7 . . ?
Fe1 C14 H14 126.3 . . ?



# END of CIF
