# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ard_ms_qz_i_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1950069'
loop_
_audit_author_name
_audit_author_address
'MOUMITA SAHA'
;UNIVERSITY OF CALCUTTA
India
;
_audit_update_record             
;
2019-08-29 deposited with the CCDC.	2019-12-18 downloaded from the CCDC.
;
_audit_creation_date             2019-07-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 I2 N2'
_chemical_formula_sum            'C14 H8 I2 N2'
_chemical_formula_weight         458.02
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.7487(17)
_cell_length_b                   8.3925(19)
_cell_length_c                   21.639(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1407.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.66
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.555
_shelx_estimated_absorpt_T_min   0.266
_exptl_absorpt_coefficient_mu    4.453
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1487 before and 0.0595 after correction. The Ratio of minimum to maximum transmission is 0.5805. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.162
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.405
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            26839
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.033
_diffrn_reflns_theta_min         1.882
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2948
_reflns_number_total             3059
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1195 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3059
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0188
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0127P)²+0.7899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0426
_refine_ls_wR_factor_ref         0.0429
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I01 I 0.14629(4) 0.90000(4) 0.53020(2) 0.05096(9) Uani 1 1 d . . . . .
I02 I 0.55068(5) 0.94321(5) 0.28979(2) 0.06269(12) Uani 1 1 d . . . . .
N003 N 0.3162(5) 0.6653(4) 0.38807(16) 0.0387(8) Uani 1 1 d . . . . .
N004 N 0.1090(5) 0.8685(5) 0.36531(18) 0.0466(9) Uani 1 1 d . . . . .
C005 C 0.2612(6) 0.8120(5) 0.38805(19) 0.0381(9) Uani 1 1 d . . . . .
C006 C 0.2571(7) 0.3914(6) 0.3619(2) 0.0505(11) Uani 1 1 d . . . . .
H006 H 0.364014 0.360465 0.377272 0.061 Uiso 1 1 calc R . . . .
C007 C 0.3600(5) 0.9774(5) 0.47792(19) 0.0396(8) Uani 1 1 d . . . . .
C008 C 0.3796(5) 0.9311(5) 0.41662(18) 0.0359(8) Uani 1 1 d . . . . .
C009 C 0.1464(9) 0.2807(6) 0.3379(2) 0.0609(13) Uani 1 1 d . . . . .
H009 H 0.178539 0.173959 0.337544 0.073 Uiso 1 1 calc R . . . .
C00A C 0.5195(6) 0.9927(6) 0.3845(2) 0.0423(10) Uani 1 1 d . . . . .
C00B C 0.2075(5) 0.5533(5) 0.36306(18) 0.0394(10) Uani 1 1 d . . . . .
C00C C 0.0062(6) 0.7612(6) 0.3417(2) 0.0500(11) Uani 1 1 d . . . . .
H00C H -0.099183 0.794582 0.325707 0.060 Uiso 1 1 calc R . . . .
C00D C 0.4787(6) 1.0749(5) 0.5066(2) 0.0441(10) Uani 1 1 d . . . . .
H00D H 0.462825 1.104586 0.547611 0.053 Uiso 1 1 calc R . . . .
C00E C 0.0464(6) 0.5973(6) 0.33907(18) 0.0431(9) Uani 1 1 d . . . . .
C00F C -0.0134(8) 0.3245(7) 0.3139(2) 0.0609(15) Uani 1 1 d . . . . .
H00F H -0.085965 0.246779 0.297650 0.073 Uiso 1 1 calc R . . . .
C00G C 0.6414(7) 1.0895(7) 0.4129(2) 0.0559(12) Uani 1 1 d . . . . .
H00G H 0.735649 1.127712 0.390782 0.067 Uiso 1 1 calc R . . . .
C00H C -0.0649(7) 0.4802(7) 0.3139(2) 0.0568(13) Uani 1 1 d . . . . .
H00H H -0.171603 0.508859 0.297708 0.068 Uiso 1 1 calc R . . . .
C00I C 0.6204(6) 1.1281(6) 0.4745(2) 0.0547(12) Uani 1 1 d . . . . .
H00I H 0.702682 1.190410 0.494400 0.066 Uiso 1 1 calc R . . . .


_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
I01 C007 2.108(4) . ?
I02 C00A 2.104(4) . ?
N003 C005 1.303(6) . ?
N003 C00B 1.373(5) . ?
N004 C005 1.363(5) . ?
N004 C00C 1.307(6) . ?
C005 C008 1.492(6) . ?
C006 H006 0.9300 . ?
C006 C009 1.367(7) . ?
C006 C00B 1.412(7) . ?
C007 C008 1.390(6) . ?
C007 C00D 1.379(6) . ?
C008 C00A 1.388(6) . ?
C009 H009 0.9300 . ?
C009 C00F 1.392(9) . ?
C00A C00G 1.390(6) . ?
C00B C00E 1.401(6) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.412(7) . ?
C00D H00D 0.9300 . ?
C00D C00I 1.374(6) . ?
C00E C00H 1.416(6) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.367(8) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.382(7) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?

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
C005 N003 C00B 116.5(4) . . ?
C00C N004 C005 115.4(4) . . ?
N003 C005 N004 127.7(4) . . ?
N003 C005 C008 115.6(4) . . ?
N004 C005 C008 116.7(4) . . ?
C009 C006 H006 120.3 . . ?
C009 C006 C00B 119.3(5) . . ?
C00B C006 H006 120.3 . . ?
C008 C007 I01 120.8(3) . . ?
C00D C007 I01 117.7(3) . . ?
C00D C007 C008 121.5(4) . . ?
C007 C008 C005 121.0(4) . . ?
C00A C008 C005 121.5(4) . . ?
C00A C008 C007 117.4(4) . . ?
C006 C009 H009 119.3 . . ?
C006 C009 C00F 121.4(5) . . ?
C00F C009 H009 119.3 . . ?
C008 C00A I02 120.3(3) . . ?
C008 C00A C00G 121.8(4) . . ?
C00G C00A I02 117.9(3) . . ?
N003 C00B C006 119.9(4) . . ?
N003 C00B C00E 120.8(4) . . ?
C00E C00B C006 119.3(4) . . ?
N004 C00C H00C 118.2 . . ?
N004 C00C C00E 123.6(4) . . ?
C00E C00C H00C 118.2 . . ?
C007 C00D H00D 120.0 . . ?
C00I C00D C007 119.9(4) . . ?
C00I C00D H00D 120.0 . . ?
C00B C00E C00C 116.0(4) . . ?
C00B C00E C00H 120.1(5) . . ?
C00C C00E C00H 123.9(5) . . ?
C009 C00F H00F 119.6 . . ?
C00H C00F C009 120.8(5) . . ?
C00H C00F H00F 119.6 . . ?
C00A C00G H00G 120.5 . . ?
C00I C00G C00A 119.0(4) . . ?
C00I C00G H00G 120.5 . . ?
C00E C00H H00H 120.5 . . ?
C00F C00H C00E 119.1(5) . . ?
C00F C00H H00H 120.5 . . ?
C00D C00I C00G 120.4(4) . . ?
C00D C00I H00I 119.8 . . ?
C00G C00I H00I 119.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_f
_database_code_depnum_ccdc_archive 'CCDC 1950441'
loop_
_audit_author_name
_audit_author_address
'MOUMITA SAHA'
;UNIVERSITY OF CALCUTTA
India
;
_audit_update_record             
;
2019-08-30 deposited with the CCDC.	2019-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 Cl N3 O2'
_chemical_formula_sum            'C13 H10 Cl N3 O2'
_chemical_formula_weight         275.69

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 0.0000 0.0000 '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 0.0060 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.7529(6)
_cell_length_b                   7.7548(6)
_cell_length_c                   23.621(2)
_cell_angle_alpha                92.139(5)
_cell_angle_beta                 91.463(5)
_cell_angle_gamma                118.775(3)
_cell_volume                     1242.40(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3165
_cell_measurement_theta_min      0.262
_cell_measurement_theta_max      0.607

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex 2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15629
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_max         24.90
_reflns_number_total             4289
_reflns_number_gt                3165
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0678P)²+7.7860P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4289
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   2.079
_refine_ls_restrained_S_all      2.079
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.033

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
Cl1 Cl 0.3322(8) 0.6904(9) 0.0145(2) 0.0911(17) Uani 1 1 d . . .
Cl2 Cl 0.3102(9) 0.6664(8) 0.4862(2) 0.0921(18) Uani 1 1 d . . .
O1 O 0.850(2) 0.581(2) 0.1309(7) 0.092(4) Uani 1 1 d . . .
O2 O 0.9697(15) 0.8215(18) 0.1942(5) 0.069(3) Uani 1 1 d . . .
O3 O 0.415(2) 0.145(2) 0.3692(6) 0.091(4) Uani 1 1 d . . .
O4 O 0.1836(18) 0.0301(15) 0.3044(5) 0.070(3) Uani 1 1 d . . .
N1 N 0.6914(15) 0.6930(15) 0.2824(5) 0.039(2) Uani 1 1 d . . .
H1 H 0.6889 0.5883 0.2680 0.047 Uiso 1 1 calc R . .
N2 N 0.8422(18) 0.7107(19) 0.1594(5) 0.052(3) Uani 1 1 d . . .
N3 N 0.6728(15) 0.9695(15) 0.2891(5) 0.042(3) Uani 1 1 d . . .
N4 N 0.0295(15) 0.3255(16) 0.2118(5) 0.045(3) Uani 1 1 d . . .
N5 N 0.2887(19) 0.1542(18) 0.3403(5) 0.052(3) Uani 1 1 d . . .
N6 N 0.3054(14) 0.3049(15) 0.2168(5) 0.040(3) Uani 1 1 d . . .
H6 H 0.4098 0.3066 0.2307 0.048 Uiso 1 1 calc R . .
C1 C 0.430(2) 0.732(2) 0.0832(6) 0.052(4) Uani 1 1 d . . .
C2 C 0.588(2) 0.703(2) 0.0951(6) 0.050(4) Uani 1 1 d . . .
H2 H 0.6417 0.6605 0.0665 0.060 Uiso 1 1 calc R . .
C3 C 0.6662(17) 0.7363(18) 0.1506(6) 0.040(3) Uani 1 1 d . . .
C4 C 0.5921(18) 0.7961(17) 0.1961(5) 0.037(3) Uani 1 1 d . . .
C5 C 0.6546(18) 0.8204(18) 0.2547(6) 0.039(3) Uani 1 1 d . . .
C6 C 0.7334(16) 0.7608(18) 0.3377(6) 0.037(3) Uani 1 1 d . . .
C7 C 0.779(2) 0.689(2) 0.3851(7) 0.057(4) Uani 1 1 d . . .
H7 H 0.7793 0.5690 0.3825 0.069 Uiso 1 1 calc R . .
C8 C 0.823(2) 0.796(3) 0.4361(7) 0.066(4) Uani 1 1 d . . .
H8 H 0.8576 0.7518 0.4682 0.079 Uiso 1 1 calc R . .
C9 C 0.430(2) 0.825(2) 0.1808(6) 0.047(3) Uani 1 1 d . . .
H9 H 0.3736 0.8664 0.2087 0.057 Uiso 1 1 calc R . .
C10 C 0.352(2) 0.792(2) 0.1256(7) 0.057(4) Uani 1 1 d . . .
H10 H 0.2455 0.8120 0.1173 0.068 Uiso 1 1 calc R . .
C11 C 0.7254(18) 0.937(2) 0.3420(6) 0.044(3) Uani 1 1 d . . .
C12 C 0.767(2) 1.049(2) 0.3944(7) 0.060(4) Uani 1 1 d . . .
H12 H 0.7617 1.1661 0.3977 0.072 Uiso 1 1 calc R . .
C13 C 0.814(2) 0.973(3) 0.4396(7) 0.064(4) Uani 1 1 d . . .
H13 H 0.8427 1.0417 0.4747 0.077 Uiso 1 1 calc R . .
C14 C 0.267(2) 0.566(2) 0.4172(6) 0.054(4) Uani 1 1 d . . .
C15 C 0.298(2) 0.411(2) 0.4053(6) 0.051(4) Uani 1 1 d . . .
H15 H 0.3417 0.3591 0.4337 0.062 Uiso 1 1 calc R . .
C16 C 0.2628(18) 0.3287(18) 0.3496(6) 0.041(3) Uani 1 1 d . . .
C17 C 0.2043(18) 0.4057(19) 0.3045(5) 0.039(3) Uani 1 1 d . . .
C18 C 0.1776(18) 0.3421(19) 0.2461(6) 0.041(3) Uani 1 1 d . . .
C19 C 0.0621(19) 0.2732(19) 0.1581(6) 0.044(3) Uani 1 1 d . . .
C20 C -0.048(2) 0.234(2) 0.1067(7) 0.060(4) Uani 1 1 d . . .
H20 H -0.1653 0.2402 0.1041 0.072 Uiso 1 1 calc R . .
C21 C 0.027(3) 0.187(3) 0.0607(7) 0.066(5) Uani 1 1 d . . .
H21 H -0.0436 0.1569 0.0260 0.080 Uiso 1 1 calc R . .
C22 C 0.174(2) 0.566(2) 0.3200(6) 0.048(3) Uani 1 1 d . . .
H22 H 0.1296 0.6199 0.2924 0.058 Uiso 1 1 calc R . .
C23 C 0.209(2) 0.646(2) 0.3754(7) 0.057(4) Uani 1 1 d . . .
H23 H 0.1919 0.7549 0.3840 0.068 Uiso 1 1 calc R . .
C24 C 0.2389(18) 0.2643(18) 0.1612(6) 0.039(3) Uani 1 1 d . . .
C25 C 0.206(3) 0.180(2) 0.0625(7) 0.065(4) Uani 1 1 d . . .
H25 H 0.2526 0.1497 0.0297 0.078 Uiso 1 1 calc R . .
C26 C 0.310(2) 0.219(2) 0.1134(7) 0.056(4) Uani 1 1 d . . .
H26 H 0.4274 0.2146 0.1157 0.067 Uiso 1 1 calc R . .


_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
Cl1 C1 1.724(15) . ?
Cl2 C14 1.731(15) . ?
O1 N2 1.221(17) . ?
O2 N2 1.215(15) . ?
O3 N5 1.210(16) . ?
O4 N5 1.207(15) . ?
N1 C5 1.340(16) . ?
N1 C6 1.361(16) . ?
N1 H1 0.8600 . ?
N2 C3 1.481(17) . ?
N3 C5 1.337(16) . ?
N3 C11 1.372(17) . ?
N4 C18 1.339(16) . ?
N4 C19 1.381(18) . ?
N5 C16 1.471(18) . ?
N6 C18 1.356(16) . ?
N6 C24 1.365(16) . ?
N6 H6 0.8600 . ?
C1 C2 1.38(2) . ?
C1 C10 1.36(2) . ?
C2 C3 1.391(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(18) . ?
C4 C9 1.419(18) . ?
C4 C5 1.429(18) . ?
C6 C11 1.399(19) . ?
C6 C7 1.378(19) . ?
C7 C8 1.38(2) . ?
C7 H7 0.9300 . ?
C8 C13 1.40(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.38(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.42(2) . ?
C12 C13 1.36(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.36(2) . ?
C14 C23 1.37(2) . ?
C15 C16 1.399(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.407(18) . ?
C17 C22 1.410(19) . ?
C17 C18 1.425(19) . ?
C19 C20 1.404(19) . ?
C19 C24 1.406(18) . ?
C20 C21 1.37(2) . ?
C20 H20 0.9300 . ?
C21 C25 1.41(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.39(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C26 1.374(19) . ?
C25 C26 1.37(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

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 N1 C6 107.0(10) . . ?
C5 N1 H1 126.5 . . ?
C6 N1 H1 126.5 . . ?
O2 N2 O1 124.3(13) . . ?
O2 N2 C3 118.0(12) . . ?
O1 N2 C3 117.7(12) . . ?
C5 N3 C11 106.3(11) . . ?
C18 N4 C19 106.6(11) . . ?
O4 N5 O3 124.3(14) . . ?
O4 N5 C16 118.1(12) . . ?
O3 N5 C16 117.6(12) . . ?
C18 N6 C24 107.8(10) . . ?
C18 N6 H6 126.1 . . ?
C24 N6 H6 126.1 . . ?
C2 C1 C10 119.7(14) . . ?
C2 C1 Cl1 119.2(12) . . ?
C10 C1 Cl1 121.1(12) . . ?
C1 C2 C3 119.0(13) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 124.0(12) . . ?
C2 C3 N2 115.7(12) . . ?
C4 C3 N2 120.3(12) . . ?
C3 C4 C9 114.0(12) . . ?
C3 C4 C5 127.5(11) . . ?
C9 C4 C5 118.4(11) . . ?
N3 C5 N1 111.8(12) . . ?
N3 C5 C4 123.3(11) . . ?
N1 C5 C4 124.8(11) . . ?
N1 C6 C11 107.2(11) . . ?
N1 C6 C7 132.3(13) . . ?
C11 C6 C7 120.4(13) . . ?
C8 C7 C6 119.0(14) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C13 119.8(15) . . ?
C7 C8 H8 120.1 . . ?
C13 C8 H8 120.1 . . ?
C10 C9 C4 122.0(13) . . ?
C10 C9 H9 119.0 . . ?
C4 C9 H9 119.0 . . ?
C9 C10 C1 121.2(14) . . ?
C9 C10 H10 119.5 . . ?
C1 C10 H10 119.3 . . ?
N3 C11 C6 107.6(12) . . ?
N3 C11 C12 131.0(14) . . ?
C6 C11 C12 121.4(14) . . ?
C13 C12 C11 115.7(15) . . ?
C13 C12 H12 122.1 . . ?
C11 C12 H12 122.1 . . ?
C12 C13 C8 123.5(15) . . ?
C12 C13 H13 118.2 . . ?
C8 C13 H13 118.2 . . ?
C15 C14 C23 120.7(14) . . ?
C15 C14 Cl2 119.1(13) . . ?
C23 C14 Cl2 120.2(13) . . ?
C14 C15 C16 119.2(14) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C17 122.8(12) . . ?
C15 C16 N5 116.3(12) . . ?
C17 C16 N5 120.9(12) . . ?
C16 C17 C22 114.9(12) . . ?
C16 C17 C18 127.2(12) . . ?
C22 C17 C18 117.8(12) . . ?
N4 C18 N6 111.0(12) . . ?
N4 C18 C17 124.1(12) . . ?
N6 C18 C17 124.8(11) . . ?
N4 C19 C20 130.6(13) . . ?
N4 C19 C24 108.0(11) . . ?
C20 C19 C24 121.4(14) . . ?
C21 C20 C19 115.6(15) . . ?
C21 C20 H20 122.2 . . ?
C19 C20 H20 122.2 . . ?
C20 C21 C25 124.1(15) . . ?
C20 C21 H21 117.9 . . ?
C25 C21 H21 118.0 . . ?
C23 C22 C17 121.8(14) . . ?
C23 C22 H22 119.1 . . ?
C17 C22 H22 119.1 . . ?
C14 C23 C22 120.4(14) . . ?
C14 C23 H23 119.7 . . ?
C22 C23 H23 119.8 . . ?
N6 C24 C26 133.0(13) . . ?
N6 C24 C19 106.5(11) . . ?
C26 C24 C19 120.5(13) . . ?
C26 C25 C21 118.6(15) . . ?
C26 C25 H25 120.7 . . ?
C21 C25 H25 120.7 . . ?
C25 C26 C24 119.8(15) . . ?
C25 C26 H26 120.1 . . ?
C24 C26 H26 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        24.90
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.048
