# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_sc874
_database_code_depnum_ccdc_archive 'CCDC 1413163'
_audit_update_record             
;
2015-07-15 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;
_publcif_datablock.id            {a6ec464d-e451-4258-a5bc-d6c38dde2ec0}


_diffrn_radiation_source         Molybdene
#Added by publCIF



_audit_creation_date             2015-01-23T14:31:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H5 Cl1 N2 O2'
_chemical_formula_sum            'C9 H5 Cl N2 O2'
_chemical_formula_weight         208.6
_chemical_compound_source        'synthesis as described'

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


_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.6985(7)
_cell_length_b                   9.6719(14)
_cell_length_c                   9.8461(14)
_cell_angle_alpha                111.248(2)
_cell_angle_beta                 92.409(2)
_cell_angle_gamma                91.899(2)
_cell_volume                     416.09(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(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       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             212
_exptl_special_details           ?

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

_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_measurement_device_type  SMART
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_number            3322
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_full        26.33
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             1668
_reflns_number_gt                1492
_reflns_threshold_expression     >2σ(I)

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

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0445P)²+0.1630P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1668
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 '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 0.1451(4) 0.7504(2) 0.2547(2) 0.0378(4) Uani 1 1 d . . .
C2 C 0.2952(4) 0.84446(19) 0.3770(2) 0.0413(4) Uani 1 1 d . . .
H2 H 0.2596 0.945 0.4104 0.05 Uiso 1 1 calc R . .
C3 C 0.5410(3) 0.65518(17) 0.40157(17) 0.0299(3) Uani 1 1 d . . .
C4 C 0.3952(4) 0.54968(17) 0.27831(17) 0.0317(4) Uani 1 1 d . . .
C5 C 0.1934(4) 0.60084(19) 0.20494(19) 0.0382(4) Uani 1 1 d . . .
H5 H 0.0908 0.5352 0.1227 0.046 Uiso 1 1 calc R . .
C6 C 0.8637(4) 0.70537(18) 0.61062(17) 0.0334(4) Uani 1 1 d . . .
H6A H 0.904 0.8025 0.6059 0.04 Uiso 1 1 calc R . .
H6B H 1.042 0.669 0.6341 0.04 Uiso 1 1 calc R . .
C7 C 0.6638(3) 0.71925(17) 0.72775(17) 0.0314(4) Uani 1 1 d . . .
C8 C 0.3963(4) 0.8181(2) 0.8996(2) 0.0468(5) Uani 1 1 d . . .
H8 H 0.2971 0.8879 0.9703 0.056 Uiso 1 1 calc R . .
C9 C 0.4426(4) 0.39015(18) 0.23250(17) 0.0329(4) Uani 1 1 d . . .
Cl1 Cl -0.10879(11) 0.81913(6) 0.16611(6) 0.05624(19) Uani 1 1 d . . .
N1 N 0.4916(3) 0.79752(15) 0.45079(16) 0.0380(3) Uani 1 1 d . . .
N2 N 0.5581(3) 0.85349(15) 0.81503(16) 0.0414(4) Uani 1 1 d . . .
O1 O 0.7451(2) 0.60491(12) 0.46999(12) 0.0335(3) Uani 1 1 d . . .
O2 O 0.3792(3) 0.67182(13) 0.87918(13) 0.0430(3) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.366(3) . ?
C1 C5 1.379(3) . ?
C1 Cl1 1.7351(17) . ?
C2 N1 1.340(2) . ?
C3 N1 1.316(2) . ?
C3 O1 1.3504(19) . ?
C3 C4 1.403(2) . ?
C4 C5 1.378(2) . ?
C4 C9 1.470(2) . ?
C6 O1 1.4477(19) . ?
C6 C7 1.489(2) . ?
C7 C9 1.343(2) 2_666 ?
C7 N2 1.393(2) . ?
C8 N2 1.278(2) . ?
C8 O2 1.354(2) . ?
C9 C7 1.343(2) 2_666 ?
C9 O2 1.379(2) 2_666 ?
O2 C9 1.379(2) 2_666 ?

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 119.33(16) . . ?
C2 C1 Cl1 119.95(14) . . ?
C5 C1 Cl1 120.71(14) . . ?
N1 C2 C1 122.58(16) . . ?
N1 C3 O1 119.56(14) . . ?
N1 C3 C4 123.67(15) . . ?
O1 C3 C4 116.76(13) . . ?
C5 C4 C3 117.14(15) . . ?
C5 C4 C9 120.75(14) . . ?
C3 C4 C9 122.04(15) . . ?
C4 C5 C1 119.29(16) . . ?
O1 C6 C7 111.38(13) . . ?
C9 C7 N2 109.15(15) 2_666 . ?
C9 C7 C6 127.26(14) 2_666 . ?
N2 C7 C6 123.59(15) . . ?
N2 C8 O2 115.30(16) . . ?
C7 C9 O2 107.88(14) 2_666 2_666 ?
C7 C9 C4 133.52(15) 2_666 . ?
O2 C9 C4 118.52(14) 2_666 . ?
C3 N1 C2 117.97(15) . . ?
C8 N2 C7 104.16(15) . . ?
C3 O1 C6 117.67(12) . . ?
C8 O2 C9 103.50(14) . 2_666 ?

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 N1 0.7(3) . . . . ?
Cl1 C1 C2 N1 179.32(14) . . . . ?
N1 C3 C4 C5 1.1(2) . . . . ?
O1 C3 C4 C5 -177.85(14) . . . . ?
N1 C3 C4 C9 -175.77(16) . . . . ?
O1 C3 C4 C9 5.2(2) . . . . ?
C3 C4 C5 C1 0.1(2) . . . . ?
C9 C4 C5 C1 177.07(15) . . . . ?
C2 C1 C5 C4 -1.0(3) . . . . ?
Cl1 C1 C5 C4 -179.59(13) . . . . ?
O1 C6 C7 C9 58.9(2) . . . 2_666 ?
O1 C6 C7 N2 -121.40(16) . . . . ?
C5 C4 C9 C7 -92.6(2) . . . 2_666 ?
C3 C4 C9 C7 84.2(2) . . . 2_666 ?
C5 C4 C9 O2 83.7(2) . . . 2_666 ?
C3 C4 C9 O2 -99.49(18) . . . 2_666 ?
O1 C3 N1 C2 177.51(15) . . . . ?
C4 C3 N1 C2 -1.4(3) . . . . ?
C1 C2 N1 C3 0.5(3) . . . . ?
O2 C8 N2 C7 -0.1(2) . . . . ?
C9 C7 N2 C8 -0.47(19) 2_666 . . . ?
C6 C7 N2 C8 179.75(16) . . . . ?
N1 C3 O1 C6 11.4(2) . . . . ?
C4 C3 O1 C6 -169.58(14) . . . . ?
C7 C6 O1 C3 76.11(17) . . . . ?
N2 C8 O2 C9 0.6(2) . . . 2_666 ?
####################################################################### 
# 
# 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_sc822
_database_code_depnum_ccdc_archive 'CCDC 1413164'
_audit_update_record             
;
2015-07-15 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;


_diffrn_measurement_device_type  SMART
#Added by publCIF



_audit_creation_date             2014-10-12T11:16:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H5 Cl1 N2 O2'
_chemical_formula_sum            'C9 H5 Cl N2 O2'
_chemical_formula_weight         208.6
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6155(11)
_cell_length_b                   7.0220(12)
_cell_length_c                   9.6435(17)
_cell_angle_alpha                82.132(3)
_cell_angle_beta                 76.879(3)
_cell_angle_gamma                71.863(3)
_cell_volume                     413.54(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(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       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             212
_exptl_special_details           ?

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

_exptl_absorpt_coefficient_mu    0.43
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_number            3312
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_reflns_number_total             1664
_reflns_number_gt                1331
_reflns_threshold_expression     >2σ(I)

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

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0888P)²+0.1314P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1664
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.059
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1415
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.07
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.071

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 '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 0.1103(4) 0.1225(4) 0.8358(2) 0.0492(6) Uani 1 1 d . . .
H1 H 0.1896 0.0823 0.9083 0.059 Uiso 1 1 calc R . .
C2 C -0.1436(4) 0.2133(3) 0.7262(2) 0.0391(5) Uani 1 1 d . . .
C3 C -0.3591(4) 0.2732(4) 0.6898(3) 0.0494(6) Uani 1 1 d . . .
H3A H -0.4395 0.182 0.7406 0.059 Uiso 1 1 calc R . .
H3B H -0.438 0.4073 0.7195 0.059 Uiso 1 1 calc R . .
C4 C -0.1635(3) 0.2828(3) 0.4407(2) 0.0374(5) Uani 1 1 d . . .
C5 C 0.0407(3) 0.2453(3) 0.4774(2) 0.0357(5) Uani 1 1 d . . .
C6 C 0.0358(3) 0.2023(3) 0.6280(2) 0.0369(5) Uani 1 1 d . . .
C7 C 0.2160(4) 0.2493(3) 0.3694(2) 0.0422(5) Uani 1 1 d . . .
H7 H 0.3537 0.2253 0.3886 0.051 Uiso 1 1 calc R . .
C8 C 0.1803(4) 0.2900(4) 0.2322(3) 0.0464(6) Uani 1 1 d . . .
C9 C -0.0240(5) 0.3263(4) 0.2056(3) 0.0519(6) Uani 1 1 d . . .
H9 H -0.0436 0.355 0.1117 0.062 Uiso 1 1 calc R . .
Cl1 Cl 0.39519(13) 0.29211(13) 0.09078(7) 0.0679(3) Uani 1 1 d . . .
N1 N -0.0881(3) 0.1604(3) 0.86099(19) 0.0440(5) Uani 1 1 d . . .
N2 N -0.1968(3) 0.3220(3) 0.3095(2) 0.0496(5) Uani 1 1 d . . .
O1 O 0.2093(2) 0.1424(3) 0.69563(16) 0.0448(4) Uani 1 1 d . . .
O2 O -0.3433(3) 0.2709(3) 0.53855(19) 0.0552(5) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 1.228(3) . ?
C1 O1 1.370(3) . ?
C1 H1 0.93 . ?
C2 C6 1.329(3) . ?
C2 N1 1.401(3) . ?
C2 C3 1.465(3) . ?
C3 O2 1.440(3) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 N2 1.311(3) . ?
C4 O2 1.358(3) . ?
C4 C5 1.411(3) . ?
C5 C7 1.377(3) . ?
C5 C6 1.437(3) . ?
C6 O1 1.373(3) . ?
C7 C8 1.372(3) . ?
C7 H7 0.93 . ?
C8 C9 1.372(4) . ?
C8 Cl1 1.735(3) . ?
C9 N2 1.344(3) . ?
C9 H9 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
N1 C1 O1 116.8(2) . . ?
N1 C1 H1 121.6 . . ?
O1 C1 H1 121.6 . . ?
C6 C2 N1 109.0(2) . . ?
C6 C2 C3 122.3(2) . . ?
N1 C2 C3 128.6(2) . . ?
O2 C3 C2 111.06(19) . . ?
O2 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
O2 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108 . . ?
N2 C4 O2 113.39(19) . . ?
N2 C4 C5 123.9(2) . . ?
O2 C4 C5 122.6(2) . . ?
C7 C5 C4 118.3(2) . . ?
C7 C5 C6 128.4(2) . . ?
C4 C5 C6 113.29(19) . . ?
C2 C6 O1 108.21(19) . . ?
C2 C6 C5 124.4(2) . . ?
O1 C6 C5 127.35(19) . . ?
C8 C7 C5 117.6(2) . . ?
C8 C7 H7 121.2 . . ?
C5 C7 H7 121.2 . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 Cl1 119.9(2) . . ?
C9 C8 Cl1 119.5(2) . . ?
N2 C9 C8 122.7(2) . . ?
N2 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
C1 N1 C2 103.96(19) . . ?
C4 N2 C9 117.0(2) . . ?
C1 O1 C6 101.97(17) . . ?
C4 O2 C3 123.00(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C2 C3 O2 13.4(3) . . . . ?
N1 C2 C3 O2 -166.8(2) . . . . ?
N2 C4 C5 C7 -0.2(3) . . . . ?
O2 C4 C5 C7 176.1(2) . . . . ?
N2 C4 C5 C6 -178.8(2) . . . . ?
O2 C4 C5 C6 -2.5(3) . . . . ?
N1 C2 C6 O1 0.2(3) . . . . ?
C3 C2 C6 O1 -180.0(2) . . . . ?
N1 C2 C6 C5 179.65(19) . . . . ?
C3 C2 C6 C5 -0.5(4) . . . . ?
C7 C5 C6 C2 175.9(2) . . . . ?
C4 C5 C6 C2 -5.7(3) . . . . ?
C7 C5 C6 O1 -4.8(4) . . . . ?
C4 C5 C6 O1 173.7(2) . . . . ?
C4 C5 C7 C8 0.1(3) . . . . ?
C6 C5 C7 C8 178.5(2) . . . . ?
C5 C7 C8 C9 0.4(4) . . . . ?
C5 C7 C8 Cl1 -178.64(16) . . . . ?
C7 C8 C9 N2 -0.8(4) . . . . ?
Cl1 C8 C9 N2 178.26(19) . . . . ?
O1 C1 N1 C2 0.2(3) . . . . ?
C6 C2 N1 C1 -0.3(3) . . . . ?
C3 C2 N1 C1 179.9(2) . . . . ?
O2 C4 N2 C9 -176.77(19) . . . . ?
C5 C4 N2 C9 -0.1(3) . . . . ?
C8 C9 N2 C4 0.6(4) . . . . ?
N1 C1 O1 C6 -0.1(3) . . . . ?
C2 C6 O1 C1 0.0(2) . . . . ?
C5 C6 O1 C1 -179.5(2) . . . . ?
N2 C4 O2 C3 -166.0(2) . . . . ?
C5 C4 O2 C3 17.3(3) . . . . ?
C2 C3 O2 C4 -21.6(3) . . . . ?
