# Electronic Supplementary Material (ESI) for ChemComm.
# 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_15231_2
_database_code_depnum_ccdc_archive 'CCDC 1425090'
_audit_update_record             
;
2015-09-15 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'2,2-dichloro-2-nitro-1-(2-nitrophenyl)ethyl benzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H20 Cl4 N4 O12'
_chemical_formula_sum            'C30 H20 Cl4 N4 O12'
_chemical_formula_weight         770.30

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9802(7)
_cell_length_b                   7.0738(7)
_cell_length_c                   17.9149(18)
_cell_angle_alpha                88.1220(10)
_cell_angle_beta                 80.5890(10)
_cell_angle_gamma                67.2930(10)
_cell_volume                     804.58(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10417
_cell_measurement_theta_min      4.612
_cell_measurement_theta_max      59.447

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.440
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5865
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'SADABS-2012/1, G. Sheldrick'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10203
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.306
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             3728
_reflns_number_gt                3546
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX 2, Bruker-AXS'
_computing_cell_refinement       'SAINT v.8.34A, Bruker-AXS'
_computing_data_reduction        'SAINT v.8.34A, Bruker-AXS'
_computing_structure_solution    'SHELXS-Version 2013/1, G. Sheldrick'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'X-SEED, L.Barbour (1999)'
_computing_publication_material  ?
_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)+(0.0596P)²+0.4403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3728
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.44504(5) 0.21395(5) 0.13191(2) 0.01725(11) Uani 1 1 d . . . . .
Cl2 Cl 0.19194(6) 0.55517(5) 0.23738(2) 0.02083(11) Uani 1 1 d . . . . .
O1 O 0.20824(18) 0.04864(17) -0.00422(6) 0.0222(2) Uani 1 1 d . . . . .
O2 O 0.16841(18) -0.07941(16) 0.10620(6) 0.0218(2) Uani 1 1 d . . . . .
O3 O 0.44586(18) -0.01292(17) 0.27850(7) 0.0235(2) Uani 1 1 d . . . . .
O4 O 0.4500(2) 0.2650(2) 0.32476(8) 0.0319(3) Uani 1 1 d . . . . .
O5 O -0.02037(16) 0.27783(15) 0.29908(6) 0.0152(2) Uani 1 1 d . . . . .
O6 O -0.0654(2) -0.02233(18) 0.30522(7) 0.0248(3) Uani 1 1 d . . . . .
N1 N 0.12748(18) 0.06417(18) 0.06287(7) 0.0155(2) Uani 1 1 d . . . . .
N2 N 0.40256(19) 0.1718(2) 0.28033(7) 0.0184(3) Uani 1 1 d . . . . .
C1 C -0.0597(2) 0.3343(2) 0.16670(8) 0.0132(3) Uani 1 1 d . . . . .
C2 C -0.2246(2) 0.5225(2) 0.18880(9) 0.0169(3) Uani 1 1 d . . . . .
H2 H -0.2480 0.5746 0.2391 0.020 Uiso 1 1 calc R U . . .
C3 C -0.3549(2) 0.6345(2) 0.13861(9) 0.0188(3) Uani 1 1 d . . . . .
H3 H -0.4683 0.7601 0.1553 0.023 Uiso 1 1 calc R U . . .
C4 C -0.3208(2) 0.5647(2) 0.06427(9) 0.0180(3) Uani 1 1 d . . . . .
H4 H -0.4091 0.6435 0.0300 0.022 Uiso 1 1 calc R U . . .
C5 C -0.1577(2) 0.3796(2) 0.03995(8) 0.0159(3) Uani 1 1 d . . . . .
H5 H -0.1316 0.3312 -0.0110 0.019 Uiso 1 1 calc R U . . .
C6 C -0.0328(2) 0.2659(2) 0.09181(8) 0.0134(3) Uani 1 1 d . . . . .
C7 C 0.0853(2) 0.2251(2) 0.22258(8) 0.0133(3) Uani 1 1 d . . . . .
H7 H 0.1393 0.0734 0.2134 0.016 Uiso 1 1 calc R U . . .
C8 C 0.2717(2) 0.2940(2) 0.21847(8) 0.0141(3) Uani 1 1 d . . . . .
C9 C -0.0826(2) 0.1328(2) 0.33618(8) 0.0154(3) Uani 1 1 d . . . . .
C10 C -0.1678(2) 0.1939(2) 0.41705(8) 0.0150(3) Uani 1 1 d . . . . .
C11 C -0.2431(2) 0.0636(2) 0.46168(9) 0.0189(3) Uani 1 1 d . . . . .
H11 H -0.2424 -0.0571 0.4397 0.023 Uiso 1 1 calc R U . . .
C12 C -0.3187(2) 0.1112(3) 0.53807(9) 0.0231(3) Uani 1 1 d . . . . .
H12 H -0.3702 0.0232 0.5686 0.028 Uiso 1 1 calc R U . . .
C13 C -0.3191(2) 0.2884(3) 0.57013(9) 0.0237(3) Uani 1 1 d . . . . .
H13 H -0.3707 0.3205 0.6225 0.028 Uiso 1 1 calc R U . . .
C14 C -0.2447(2) 0.4181(3) 0.52594(9) 0.0233(3) Uani 1 1 d . . . . .
H14 H -0.2451 0.5384 0.5482 0.028 Uiso 1 1 calc R U . . .
C15 C -0.1694(2) 0.3723(2) 0.44907(9) 0.0187(3) Uani 1 1 d . . . . .
H15 H -0.1195 0.4615 0.4186 0.022 Uiso 1 1 calc R U . . .


_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 C8 1.7620(14) . ?
Cl2 C8 1.7386(14) . ?
O1 N1 1.2303(17) . ?
O2 N1 1.2298(17) . ?
O3 N2 1.2223(17) . ?
O4 N2 1.2113(17) . ?
O5 C9 1.3739(17) . ?
O5 C7 1.4324(16) . ?
O6 C9 1.2011(18) . ?
N1 C6 1.4773(17) . ?
N2 C8 1.5713(18) . ?
C1 C2 1.3988(18) . ?
C1 C6 1.3999(19) . ?
C1 C7 1.5166(18) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3946(19) . ?
C5 H5 0.9500 . ?
C7 C8 1.5463(19) . ?
C7 H7 1.0000 . ?
C9 C10 1.4833(19) . ?
C10 C11 1.398(2) . ?
C10 C15 1.398(2) . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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
C9 O5 C7 116.01(10) . . ?
O2 N1 O1 123.76(12) . . ?
O2 N1 C6 118.58(12) . . ?
O1 N1 C6 117.63(12) . . ?
O4 N2 O3 126.22(13) . . ?
O4 N2 C8 118.80(12) . . ?
O3 N2 C8 114.98(11) . . ?
C2 C1 C6 116.71(12) . . ?
C2 C1 C7 118.83(12) . . ?
C6 C1 C7 124.34(12) . . ?
C3 C2 C1 121.26(13) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 120.58(13) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.91(13) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 118.71(13) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 122.77(12) . . ?
C5 C6 N1 115.28(12) . . ?
C1 C6 N1 121.92(12) . . ?
O5 C7 C1 111.23(11) . . ?
O5 C7 C8 103.29(10) . . ?
C1 C7 C8 112.23(11) . . ?
O5 C7 H7 110.0 . . ?
C1 C7 H7 110.0 . . ?
C8 C7 H7 110.0 . . ?
C7 C8 N2 105.95(11) . . ?
C7 C8 Cl2 113.07(9) . . ?
N2 C8 Cl2 108.93(9) . . ?
C7 C8 Cl1 111.26(9) . . ?
N2 C8 Cl1 104.99(9) . . ?
Cl2 C8 Cl1 112.10(8) . . ?
O6 C9 O5 122.57(14) . . ?
O6 C9 C10 126.32(14) . . ?
O5 C9 C10 111.11(12) . . ?
C11 C10 C15 120.28(13) . . ?
C11 C10 C9 117.64(13) . . ?
C15 C10 C9 122.07(13) . . ?
C12 C11 C10 119.76(14) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 119.99(15) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.37(15) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.11(15) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 119.50(15) . . ?
C14 C15 H15 120.3 . . ?
C10 C15 H15 120.3 . . ?

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.079



#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diisopropyl ether, THF'
####################################################################### 
# 
# 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_B15242_2
_database_code_depnum_ccdc_archive 'CCDC 1425091'
_audit_update_record             
;
2015-09-15 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'2,2-dichloro-2-nitro-1-(4-nitrophenyl)ethyl benzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 Cl2 N2 O6'
_chemical_formula_sum            'C15 H10 Cl2 N2 O6'
_chemical_formula_weight         385.15

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

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

_cell_length_a                   7.0035(5)
_cell_length_b                   37.401(3)
_cell_length_c                   6.0429(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1582.86(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    17971
_cell_measurement_theta_min      2.723
_cell_measurement_theta_max      30.465

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.447
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6383
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS-2012/1, G. Sheldrick'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20028
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         30.490
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4658
_reflns_number_gt                4512
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_max     0.942
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       'APEX 2, BRUKER-AXS'
_computing_cell_refinement       'SAINT v. 8.34A, BRUKER-AXS'
_computing_data_reduction        'SAINT v. 8.34A, BRUKER-AXS'
_computing_structure_solution    'SHELXT-2013/1, G. Sheldrick'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'X-SEED, L. Barbour (1999)'
_computing_publication_material  ?
_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)+(0.0399P)²+0.3519P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1941 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4658
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0668
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Cl2 Cl 0.72517(6) 0.63780(2) 0.63137(8) 0.01757(10) Uani 1 1 d . . . . .
Cl1 Cl 0.80683(6) 0.67628(2) 0.22653(8) 0.01738(10) Uani 1 1 d . . . . .
O5 O 0.41191(18) 0.60409(3) 0.3287(2) 0.0123(2) Uani 1 1 d . . . . .
O2 O 0.0084(2) 0.73601(4) 0.9751(3) 0.0220(3) Uani 1 1 d . . . . .
O1 O 0.1226(2) 0.77696(3) 0.7584(3) 0.0210(3) Uani 1 1 d . . . . .
O6 O 0.2192(2) 0.60720(4) 0.0298(3) 0.0200(3) Uani 1 1 d . . . . .
O3 O 0.8805(2) 0.58701(4) 0.3531(3) 0.0255(3) Uani 1 1 d . . . . .
O4 O 0.7372(2) 0.60102(4) 0.0471(3) 0.0256(3) Uani 1 1 d . . . . .
N1 N 0.0965(2) 0.74556(4) 0.8088(3) 0.0145(3) Uani 1 1 d . . . . .
N2 N 0.7787(2) 0.60574(4) 0.2411(3) 0.0157(3) Uani 1 1 d . . . . .
C3 C 0.1777(2) 0.71780(5) 0.6640(3) 0.0128(3) Uani 1 1 d . . . . .
C9 C 0.2921(2) 0.58955(5) 0.1735(3) 0.0119(3) Uani 1 1 d . . . . .
C5 C 0.2723(2) 0.65727(4) 0.6107(3) 0.0131(3) Uani 1 1 d . . . . .
H5 H 0.2767 0.6331 0.6584 0.016 Uiso 1 1 calc R U . . .
C4 C 0.1798(2) 0.68273(4) 0.7394(3) 0.0136(3) Uani 1 1 d . . . . .
H4 H 0.1199 0.6763 0.8748 0.016 Uiso 1 1 calc R U . . .
C7 C 0.4735(2) 0.63990(4) 0.2836(3) 0.0106(3) Uani 1 1 d . . . . .
H7 H 0.4608 0.6448 0.1217 0.013 Uiso 1 1 calc R U . . .
C6 C 0.3584(2) 0.66706(4) 0.4124(3) 0.0108(3) Uani 1 1 d . . . . .
C2 C 0.2540(2) 0.72793(4) 0.4619(3) 0.0136(3) Uani 1 1 d . . . . .
H2 H 0.2445 0.7519 0.4118 0.016 Uiso 1 1 calc R U . . .
C11 C 0.3430(2) 0.53261(5) 0.3882(3) 0.0133(3) Uani 1 1 d . . . . .
H11 H 0.4032 0.5456 0.5037 0.016 Uiso 1 1 calc R U . . .
C1 C 0.3448(2) 0.70206(4) 0.3342(3) 0.0127(3) Uani 1 1 d . . . . .
H1 H 0.3973 0.7082 0.1944 0.015 Uiso 1 1 calc R U . . .
C12 C 0.3251(3) 0.49554(5) 0.4017(3) 0.0157(3) Uani 1 1 d . . . . .
H12 H 0.3724 0.4832 0.5277 0.019 Uiso 1 1 calc R U . . .
C15 C 0.1808(2) 0.53150(5) 0.0334(3) 0.0140(3) Uani 1 1 d . . . . .
H15 H 0.1299 0.5438 -0.0907 0.017 Uiso 1 1 calc R U . . .
C10 C 0.2711(2) 0.55038(4) 0.2024(3) 0.0112(3) Uani 1 1 d . . . . .
C13 C 0.2380(2) 0.47662(4) 0.2308(4) 0.0159(3) Uani 1 1 d . . . . .
H13 H 0.2281 0.4513 0.2395 0.019 Uiso 1 1 calc R U . . .
C14 C 0.1655(3) 0.49453(5) 0.0476(3) 0.0160(3) Uani 1 1 d . . . . .
H14 H 0.1055 0.4815 -0.0680 0.019 Uiso 1 1 calc R U . . .
C8 C 0.6870(3) 0.63980(4) 0.3478(3) 0.0123(3) Uani 1 1 d . . . . .


_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
Cl2 C8 1.7357(19) . ?
Cl1 C8 1.7617(17) . ?
O5 C9 1.371(2) . ?
O5 C7 1.4332(18) . ?
O2 N1 1.232(2) . ?
O1 N1 1.227(2) . ?
O6 C9 1.204(2) . ?
O3 N2 1.207(2) . ?
O4 N2 1.220(2) . ?
N1 C3 1.472(2) . ?
N2 C8 1.566(2) . ?
C3 C4 1.389(2) . ?
C3 C2 1.386(3) . ?
C9 C10 1.483(2) . ?
C5 C6 1.391(2) . ?
C5 C4 1.389(2) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C7 C6 1.512(2) . ?
C7 C8 1.545(2) . ?
C7 H7 1.0000 . ?
C6 C1 1.395(2) . ?
C2 C1 1.391(2) . ?
C2 H2 0.9500 . ?
C11 C12 1.395(2) . ?
C11 C10 1.398(2) . ?
C11 H11 0.9500 . ?
C1 H1 0.9500 . ?
C12 C13 1.392(3) . ?
C12 H12 0.9500 . ?
C15 C14 1.390(2) . ?
C15 C10 1.393(2) . ?
C15 H15 0.9500 . ?
C13 C14 1.390(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
C9 O5 C7 115.12(13) . . ?
O2 N1 O1 123.68(16) . . ?
O2 N1 C3 118.30(15) . . ?
O1 N1 C3 118.01(16) . . ?
O3 N2 O4 126.53(17) . . ?
O3 N2 C8 118.90(16) . . ?
O4 N2 C8 114.57(15) . . ?
C4 C3 C2 122.90(16) . . ?
C4 C3 N1 118.36(17) . . ?
C2 C3 N1 118.70(15) . . ?
O6 C9 O5 122.37(16) . . ?
O6 C9 C10 125.77(16) . . ?
O5 C9 C10 111.83(14) . . ?
C6 C5 C4 120.26(16) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C3 C4 C5 117.95(17) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
O5 C7 C6 111.70(13) . . ?
O5 C7 C8 103.95(12) . . ?
C6 C7 C8 112.84(13) . . ?
O5 C7 H7 109.4 . . ?
C6 C7 H7 109.4 . . ?
C8 C7 H7 109.4 . . ?
C5 C6 C1 120.61(16) . . ?
C5 C6 C7 119.84(14) . . ?
C1 C6 C7 119.51(15) . . ?
C3 C2 C1 118.35(15) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C12 C11 C10 119.16(16) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C2 C1 C6 119.74(16) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C13 C12 C11 120.07(17) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C15 C10 119.61(17) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C15 C10 C11 120.72(15) . . ?
C15 C10 C9 117.36(15) . . ?
C11 C10 C9 121.90(15) . . ?
C14 C13 C12 120.38(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.03(17) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C7 C8 N2 107.19(13) . . ?
C7 C8 Cl2 113.41(12) . . ?
N2 C8 Cl2 107.97(12) . . ?
C7 C8 Cl1 110.78(11) . . ?
N2 C8 Cl1 105.25(11) . . ?
Cl2 C8 Cl1 111.76(10) . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.061


#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform, Hexanes'
