# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1060082'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H10 Cl2 N2 O3'
_chemical_formula_weight         301.1
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
_cell_length_a                   7.7629(16)
_cell_length_b                   23.525(5)
_cell_length_c                   7.3900(18)
_cell_angle_alpha                90
_cell_angle_beta                 111.49(2)
_cell_angle_gamma                90
_cell_volume                     1255.8(5)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    10
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.5922
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      10
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           ?
_diffrn_radiation_source         ?
_diffrn_radiation_wavelength     -1
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            10207
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         79.78
_diffrn_reflns_theta_full        13.97
_diffrn_measured_fraction_theta_max 0
_diffrn_measured_fraction_theta_full 0.9
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    0.097
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -58
_diffrn_reflns_limit_k_max       59
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          neutron

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             10207
_reflns_number_gt                9069
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0855
_refine_ls_wR_factor_gt          0.1759
_refine_ls_R_factor_all          0.0937
_refine_ls_wR_factor_ref         0.1775
_refine_ls_goodness_of_fit_ref   2.90
_refine_ls_goodness_of_fit_gt    3.05
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         10207
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    refall
_refine_ls_shift/su_max          0.0211
_refine_ls_shift/su_mean         0.0017
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef       33.8(7)
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_length_neutron
_atom_type_scat_source
C 6.646 International_Tables_Vol_C
H -3.739 International_Tables_Vol_C
Cl 9.577 International_Tables_Vol_C
N 9.360 International_Tables_Vol_C
O 5.803 International_Tables_Vol_C

_computing_data_collection       unknown
_computing_cell_refinement       unknown
_computing_data_reduction        unknown
_computing_structure_solution    unknown
_computing_structure_refinement  ?
_computing_molecular_graphics    unknown
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5349(3) 0.63565(8) 0.3738(4) Uani 0.0068(6) 4 1 d . . .
O2 O 0.8259(3) 0.87936(8) 0.6500(4) Uani 0.0085(7) 4 1 d . . .
O3 O 0.5566(3) 0.89991(8) 0.4368(4) Uani 0.0096(7) 4 1 d . . .
N2 N 0.67625(19) 0.86491(5) 0.5273(2) Uani 0.0054(4) 4 1 d . . .
Cl1 Cl 0.22958(17) 0.70930(5) 0.1434(2) Uani 0.0060(4) 4 1 d . . .
Cl2 Cl 0.90340(17) 0.65984(5) 0.6849(2) Uani 0.0054(4) 4 1 d . . .
C1 C 0.5692(3) 0.68820(7) 0.4104(3) Uani 0.0046(5) 4 1 d . . .
C2 C 0.4387(2) 0.73125(7) 0.3146(3) Uani 0.0051(5) 4 1 d . . .
C3 C 0.4710(3) 0.78864(7) 0.3473(3) Uani 0.0040(5) 4 1 d . . .
C4 C 0.6400(3) 0.80568(7) 0.4910(3) Uani 0.0044(5) 4 1 d . . .
C5 C 0.7736(3) 0.76620(7) 0.5943(3) Uani 0.0058(6) 4 1 d . . .
C6 C 0.7377(2) 0.70924(7) 0.5555(3) Uani 0.0044(5) 4 1 d . . .
H2 H 0.3675(6) 0.82017(17) 0.2695(8) Uani 0.0207(16) 4 1 d . . .
H3 H 0.9030(6) 0.78076(18) 0.7046(7) Uani 0.0183(14) 4 1 d . . .
N1 N 0.69509(19) 0.54088(5) 0.4808(2) Uani 0.0058(4) 4 1 d . . .
C7 C 0.7266(3) 0.52205(7) 0.6617(3) Uani 0.0057(5) 4 1 d . . .
C8 C 0.7840(2) 0.46644(7) 0.7152(3) Uani 0.0052(5) 4 1 d . . .
C9 C 0.8088(3) 0.43085(7) 0.5754(3) Uani 0.0061(6) 4 1 d . . .
C10 C 0.7761(3) 0.45156(7) 0.3886(3) Uani 0.0066(6) 4 1 d . . .
C11 C 0.7192(3) 0.50736(7) 0.3470(3) Uani 0.0065(6) 4 1 d . . .
C12 C 0.8139(3) 0.44602(8) 0.9167(3) Uani 0.0084(6) 4 1 d . . .
H1 H 0.6440(7) 0.58600(18) 0.4461(7) Uani 0.0195(15) 4 1 d . . .
H4 H 0.7012(7) 0.55260(18) 0.7578(7) Uani 0.0209(16) 4 1 d . . .
H5 H 0.8509(7) 0.38694(17) 0.6120(9) Uani 0.0252(18) 4 1 d . . .
H6 H 0.7914(7) 0.42438(19) 0.2795(8) Uani 0.0236(17) 4 1 d . . .
H7 H 0.6895(7) 0.52668(18) 0.2028(8) Uani 0.0237(17) 4 1 d . . .
H8 H 0.9389(8) 0.4207(2) 0.9727(10) Uani 0.034(2) 4 1 d . . .
H9 H 0.8249(9) 0.48220(19) 1.0150(8) Uani 0.0282(19) 4 1 d . . .
H10 H 0.6997(8) 0.4193(2) 0.9175(10) Uani 0.036(2) 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
? ? ? ? ? ? ? ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 11. STRUCTURE-FACTOR LIST


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1060083'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H10 Cl2 N2 O3'
_chemical_formula_weight         301.1
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
_cell_length_a                   7.762(2)
_cell_length_b                   23.519(7)
_cell_length_c                   7.387(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.47(2)
_cell_angle_gamma                90
_cell_volume                     1255.0(7)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    30
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.5933
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      30
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           ?
_diffrn_radiation_source         ?
_diffrn_radiation_wavelength     -1
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            9693
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         79.87
_diffrn_reflns_theta_full        14.9
_diffrn_measured_fraction_theta_max 0
_diffrn_measured_fraction_theta_full 0.89
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    0.0976
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -58
_diffrn_reflns_limit_k_max       58
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          neutron

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             9693
_reflns_number_gt                8591
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0901
_refine_ls_wR_factor_gt          0.1729
_refine_ls_R_factor_all          0.0991
_refine_ls_wR_factor_ref         0.1871
_refine_ls_goodness_of_fit_ref   3.03
_refine_ls_goodness_of_fit_gt    2.98
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         9693
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    refall
_refine_ls_shift/su_max          0.0212
_refine_ls_shift/su_mean         0.0014
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef       35.1(8)
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_length_neutron
_atom_type_scat_source
C 6.646 International_Tables_Vol_C
H -3.739 International_Tables_Vol_C
Cl 9.577 International_Tables_Vol_C
N 9.360 International_Tables_Vol_C
O 5.803 International_Tables_Vol_C

_computing_data_collection       unknown
_computing_cell_refinement       unknown
_computing_data_reduction        unknown
_computing_structure_solution    unknown
_computing_structure_refinement  ?
_computing_molecular_graphics    unknown
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5335(3) 0.63557(9) 0.3732(4) Uani 0.0077(7) 4 1 d . . .
O2 O 0.8271(3) 0.87953(9) 0.6507(4) Uani 0.0103(8) 4 1 d . . .
O3 O 0.5565(3) 0.90030(9) 0.4364(4) Uani 0.0091(8) 4 1 d . . .
N2 N 0.6766(2) 0.86494(6) 0.5275(2) Uani 0.0069(4) 4 1 d . . .
Cl1 Cl 0.22991(20) 0.70907(5) 0.1437(2) Uani 0.0070(4) 4 1 d . . .
Cl2 Cl 0.90279(19) 0.66012(5) 0.6837(2) Uani 0.0069(4) 4 1 d . . .
C1 C 0.5692(3) 0.68814(8) 0.4114(3) Uani 0.0060(6) 4 1 d . . .
C2 C 0.4385(3) 0.73145(7) 0.3145(3) Uani 0.0055(6) 4 1 d . . .
C3 C 0.4712(3) 0.78881(8) 0.3479(3) Uani 0.0060(6) 4 1 d . . .
C4 C 0.6400(3) 0.80574(8) 0.4897(3) Uani 0.0057(6) 4 1 d . . .
C5 C 0.7730(3) 0.76589(8) 0.5937(3) Uani 0.0065(6) 4 1 d . . .
C6 C 0.7374(3) 0.70907(8) 0.5543(3) Uani 0.0062(6) 4 1 d . . .
H2 H 0.3684(7) 0.81924(19) 0.2702(8) Uani 0.0214(17) 4 1 d . . .
H3 H 0.9023(7) 0.7809(2) 0.7038(8) Uani 0.0230(17) 4 1 d . . .
N1 N 0.6950(2) 0.54062(5) 0.4806(2) Uani 0.0071(4) 4 1 d . . .
C7 C 0.7264(3) 0.52184(8) 0.6621(3) Uani 0.0068(6) 4 1 d . . .
C8 C 0.7847(3) 0.46647(8) 0.7154(3) Uani 0.0066(6) 4 1 d . . .
C9 C 0.8086(3) 0.43102(7) 0.5758(3) Uani 0.0071(6) 4 1 d . . .
C10 C 0.7754(3) 0.45162(8) 0.3903(3) Uani 0.0076(6) 4 1 d . . .
C11 C 0.7178(3) 0.50702(7) 0.3458(4) Uani 0.0067(6) 4 1 d . . .
C12 C 0.8137(3) 0.44605(9) 0.9174(3) Uani 0.0098(6) 4 1 d . . .
H1 H 0.6398(7) 0.58559(19) 0.4437(9) Uani 0.0220(18) 4 1 d . . .
H4 H 0.7044(7) 0.55306(19) 0.7612(8) Uani 0.0233(19) 4 1 d . . .
H5 H 0.8508(8) 0.3874(2) 0.6123(8) Uani 0.0264(19) 4 1 d . . .
H6 H 0.7923(7) 0.4233(2) 0.2786(8) Uani 0.0225(18) 4 1 d . . .
H7 H 0.6895(8) 0.5263(2) 0.2022(8) Uani 0.0266(19) 4 1 d . . .
H8 H 0.9370(9) 0.4202(2) 0.9747(10) Uani 0.033(2) 4 1 d . . .
H9 H 0.8221(9) 0.4815(2) 1.0136(10) Uani 0.033(2) 4 1 d . . .
H10 H 0.7026(8) 0.4191(3) 0.9160(10) Uani 0.034(2) 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
? ? ? ? ? ? ? ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 11. STRUCTURE-FACTOR LIST


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1060084'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H10 Cl2 N2 O3'
_chemical_formula_weight         301.1
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
_cell_length_a                   7.766(2)
_cell_length_b                   23.537(7)
_cell_length_c                   7.395(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.51(2)
_cell_angle_gamma                90
_cell_volume                     1257.6(7)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    50
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.59
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      50
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           ?
_diffrn_radiation_source         ?
_diffrn_radiation_wavelength     -1
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            9008
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         79.41
_diffrn_reflns_theta_full        14.08
_diffrn_measured_fraction_theta_max 0
_diffrn_measured_fraction_theta_full 0.9
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    0.097
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -57
_diffrn_reflns_limit_k_max       61
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          neutron

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             9008
_reflns_number_gt                7930
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_gt          0.1581
_refine_ls_R_factor_all          0.0901
_refine_ls_wR_factor_ref         0.1601
_refine_ls_goodness_of_fit_ref   2.59
_refine_ls_goodness_of_fit_gt    2.73
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         9008
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    refall
_refine_ls_shift/su_max          0.0071
_refine_ls_shift/su_mean         0.0006
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef       36.3(7)
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_length_neutron
_atom_type_scat_source
C 6.646 International_Tables_Vol_C
H -3.739 International_Tables_Vol_C
Cl 9.577 International_Tables_Vol_C
N 9.360 International_Tables_Vol_C
O 5.803 International_Tables_Vol_C

_computing_data_collection       unknown
_computing_cell_refinement       unknown
_computing_data_reduction        unknown
_computing_structure_solution    unknown
_computing_structure_refinement  ?
_computing_molecular_graphics    unknown
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5353(3) 0.63569(8) 0.3729(4) Uani 0.0094(7) 4 1 d . . .
O2 O 0.8264(3) 0.87952(9) 0.6505(4) Uani 0.0134(8) 4 1 d . . .
O3 O 0.5567(3) 0.89988(8) 0.4363(4) Uani 0.0118(8) 4 1 d . . .
N2 N 0.67660(19) 0.86488(5) 0.5276(2) Uani 0.0088(4) 4 1 d . . .
Cl1 Cl 0.23035(18) 0.70935(5) 0.1439(2) Uani 0.0093(4) 4 1 d . . .
Cl2 Cl 0.90341(18) 0.65996(5) 0.6836(2) Uani 0.0097(4) 4 1 d . . .
C1 C 0.5700(3) 0.68823(7) 0.4112(3) Uani 0.0075(6) 4 1 d . . .
C2 C 0.4395(3) 0.73145(7) 0.3147(3) Uani 0.0072(5) 4 1 d . . .
C3 C 0.4720(3) 0.78845(7) 0.3479(3) Uani 0.0074(5) 4 1 d . . .
C4 C 0.6403(3) 0.80570(7) 0.4898(3) Uani 0.0068(5) 4 1 d . . .
C5 C 0.7738(3) 0.76606(7) 0.5938(3) Uani 0.0081(6) 4 1 d . . .
C6 C 0.7382(2) 0.70945(7) 0.5544(3) Uani 0.0069(5) 4 1 d . . .
H2 H 0.3681(6) 0.82005(16) 0.2708(7) Uani 0.0234(16) 4 1 d . . .
H3 H 0.9029(6) 0.78051(17) 0.7044(7) Uani 0.0218(15) 4 1 d . . .
N1 N 0.69547(19) 0.54088(5) 0.4810(2) Uani 0.0091(4) 4 1 d . . .
C7 C 0.7269(3) 0.52197(7) 0.6619(3) Uani 0.0077(6) 4 1 d . . .
C8 C 0.7839(3) 0.46666(7) 0.7156(3) Uani 0.0081(6) 4 1 d . . .
C9 C 0.8085(3) 0.43104(7) 0.5757(3) Uani 0.0084(6) 4 1 d . . .
C10 C 0.7760(3) 0.45162(7) 0.3900(3) Uani 0.0090(6) 4 1 d . . .
C11 C 0.7185(3) 0.50731(7) 0.3459(3) Uani 0.0089(6) 4 1 d . . .
C12 C 0.8130(3) 0.44609(8) 0.9171(3) Uani 0.0109(6) 4 1 d . . .
H1 H 0.6430(6) 0.58561(17) 0.4434(7) Uani 0.0232(16) 4 1 d . . .
H4 H 0.7025(7) 0.55270(18) 0.7605(8) Uani 0.0272(18) 4 1 d . . .
H5 H 0.8503(7) 0.38747(17) 0.6129(8) Uani 0.0256(17) 4 1 d . . .
H6 H 0.7911(7) 0.42394(19) 0.2787(7) Uani 0.0252(17) 4 1 d . . .
H7 H 0.6899(7) 0.52676(18) 0.2026(7) Uani 0.0272(17) 4 1 d . . .
H8 H 0.9390(8) 0.4206(2) 0.9746(8) Uani 0.036(2) 4 1 d . . .
H9 H 0.8243(9) 0.4819(2) 1.0125(8) Uani 0.039(2) 4 1 d . . .
H10 H 0.7003(7) 0.4192(2) 0.9154(9) Uani 0.037(2) 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
? ? ? ? ? ? ? ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 11. STRUCTURE-FACTOR LIST


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1060085'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H10 Cl2 N2 O3'
_chemical_formula_weight         301.1
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
_cell_length_a                   7.780(2)
_cell_length_b                   23.541(7)
_cell_length_c                   7.405(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.59(2)
_cell_angle_gamma                90
_cell_volume                     1261.1(7)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    80
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.5855
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      80
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           ?
_diffrn_radiation_source         ?
_diffrn_radiation_wavelength     -1
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            7985
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         70.6
_diffrn_reflns_theta_full        13.32
_diffrn_measured_fraction_theta_max 0
_diffrn_measured_fraction_theta_full 0.91
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    0.0993
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -57
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          neutron

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             7985
_reflns_number_gt                6946
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0794
_refine_ls_wR_factor_gt          0.1603
_refine_ls_R_factor_all          0.0891
_refine_ls_wR_factor_ref         0.1638
_refine_ls_goodness_of_fit_ref   2.63
_refine_ls_goodness_of_fit_gt    2.76
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         7985
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    refall
_refine_ls_shift/su_max          0.0081
_refine_ls_shift/su_mean         0.0006
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef       37.2(8)
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_length_neutron
_atom_type_scat_source
C 6.646 International_Tables_Vol_C
H -3.739 International_Tables_Vol_C
Cl 9.577 International_Tables_Vol_C
N 9.360 International_Tables_Vol_C
O 5.803 International_Tables_Vol_C

_computing_data_collection       unknown
_computing_cell_refinement       unknown
_computing_data_reduction        unknown
_computing_structure_solution    unknown
_computing_structure_refinement  ?
_computing_molecular_graphics    unknown
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5368(3) 0.63573(9) 0.3737(4) Uani 0.0132(8) 4 1 d . . .
O2 O 0.8268(4) 0.87942(10) 0.6498(5) Uani 0.0184(10) 4 1 d . . .
O3 O 0.5577(4) 0.89996(10) 0.4363(4) Uani 0.0159(9) 4 1 d . . .
N2 N 0.6776(2) 0.86484(6) 0.5276(3) Uani 0.0120(5) 4 1 d . . .
Cl1 Cl 0.2315(2) 0.70945(6) 0.1444(3) Uani 0.0128(5) 4 1 d . . .
Cl2 Cl 0.9045(2) 0.66019(6) 0.6834(3) Uani 0.0151(5) 4 1 d . . .
C1 C 0.5716(3) 0.68837(8) 0.4116(3) Uani 0.0097(7) 4 1 d . . .
C2 C 0.4406(3) 0.73141(8) 0.3150(3) Uani 0.0095(6) 4 1 d . . .
C3 C 0.4728(3) 0.78853(8) 0.3479(3) Uani 0.0098(7) 4 1 d . . .
C4 C 0.6413(3) 0.80565(8) 0.4897(3) Uani 0.0096(7) 4 1 d . . .
C5 C 0.7744(3) 0.76627(8) 0.5933(3) Uani 0.0103(7) 4 1 d . . .
C6 C 0.7389(3) 0.70938(8) 0.5543(3) Uani 0.0097(7) 4 1 d . . .
H2 H 0.3703(7) 0.82001(18) 0.2711(8) Uani 0.0259(18) 4 1 d . . .
H3 H 0.9051(7) 0.7807(2) 0.7042(9) Uani 0.0277(19) 4 1 d . . .
N1 N 0.6961(2) 0.54109(6) 0.4812(3) Uani 0.0126(5) 4 1 d . . .
C7 C 0.7266(3) 0.52220(8) 0.6617(4) Uani 0.0116(7) 4 1 d . . .
C8 C 0.7828(3) 0.46665(8) 0.7149(3) Uani 0.0112(7) 4 1 d . . .
C9 C 0.8075(3) 0.43126(8) 0.5756(4) Uani 0.0116(7) 4 1 d . . .
C10 C 0.7757(3) 0.45177(8) 0.3904(4) Uani 0.0127(7) 4 1 d . . .
C11 C 0.7194(3) 0.50762(8) 0.3460(4) Uani 0.0122(7) 4 1 d . . .
C12 C 0.8119(3) 0.44628(9) 0.9166(4) Uani 0.0158(8) 4 1 d . . .
H1 H 0.6433(8) 0.58601(20) 0.4446(9) Uani 0.030(2) 4 1 d . . .
H4 H 0.7032(8) 0.5528(2) 0.7608(9) Uani 0.032(2) 4 1 d . . .
H5 H 0.8490(8) 0.38774(19) 0.6118(8) Uani 0.0287(19) 4 1 d . . .
H6 H 0.7904(8) 0.4243(2) 0.2794(8) Uani 0.032(2) 4 1 d . . .
H7 H 0.6912(8) 0.5271(2) 0.2040(9) Uani 0.032(2) 4 1 d . . .
H8 H 0.9377(9) 0.4208(3) 0.9740(10) Uani 0.044(3) 4 1 d . . .
H9 H 0.8224(11) 0.4818(2) 1.0114(10) Uani 0.047(3) 4 1 d . . .
H10 H 0.6999(9) 0.4192(3) 0.9135(10) Uani 0.045(3) 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
? ? ? ? ? ? ? ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 11. STRUCTURE-FACTOR LIST


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1060086'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H10 Cl2 N2 O3'
_chemical_formula_weight         301.1
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
_cell_length_a                   7.792(2)
_cell_length_b                   23.565(7)
_cell_length_c                   7.419(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.70(2)
_cell_angle_gamma                90
_cell_volume                     1265.8(7)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    110
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.5797
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      110
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           ?
_diffrn_radiation_source         ?
_diffrn_radiation_wavelength     -1
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            7480
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         74.51
_diffrn_reflns_theta_full        13.36
_diffrn_measured_fraction_theta_max 0
_diffrn_measured_fraction_theta_full 0.92
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    0.0894
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_k_max       57
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          neutron

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             7478
_reflns_number_gt                6546
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0879
_refine_ls_wR_factor_gt          0.1799
_refine_ls_R_factor_all          0.0962
_refine_ls_wR_factor_ref         0.1849
_refine_ls_goodness_of_fit_ref   3.19
_refine_ls_goodness_of_fit_gt    3.32
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         7478
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    refall
_refine_ls_shift/su_max          0.0085
_refine_ls_shift/su_mean         0.0010
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef       35.5(9)
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_length_neutron
_atom_type_scat_source
C 6.646 International_Tables_Vol_C
H -3.739 International_Tables_Vol_C
Cl 9.577 International_Tables_Vol_C
N 9.360 International_Tables_Vol_C
O 5.803 International_Tables_Vol_C

_computing_data_collection       unknown
_computing_cell_refinement       unknown
_computing_data_reduction        unknown
_computing_structure_solution    unknown
_computing_structure_refinement  ?
_computing_molecular_graphics    unknown
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5390(4) 0.63577(11) 0.3756(5) Uani 0.0182(11) 4 1 d . . .
O2 O 0.8274(5) 0.87948(13) 0.6485(6) Uani 0.0257(13) 4 1 d . . .
O3 O 0.5617(5) 0.89987(12) 0.4396(6) Uani 0.0221(13) 4 1 d . . .
N2 N 0.6786(3) 0.86503(7) 0.5274(3) Uani 0.0161(7) 4 1 d . . .
Cl1 Cl 0.2325(2) 0.70939(7) 0.1438(3) Uani 0.0168(6) 4 1 d . . .
Cl2 Cl 0.9044(3) 0.66036(7) 0.6814(3) Uani 0.0206(7) 4 1 d . . .
C1 C 0.5751(3) 0.68838(10) 0.4154(4) Uani 0.0130(9) 4 1 d . . .
C2 C 0.4428(3) 0.73173(10) 0.3165(4) Uani 0.0122(8) 4 1 d . . .
C3 C 0.4736(3) 0.78858(9) 0.3471(4) Uani 0.0120(8) 4 1 d . . .
C4 C 0.6408(3) 0.80562(9) 0.4881(4) Uani 0.0130(9) 4 1 d . . .
C5 C 0.7768(4) 0.76605(10) 0.5947(4) Uani 0.0145(9) 4 1 d . . .
C6 C 0.7402(3) 0.70945(10) 0.5538(4) Uani 0.0125(8) 4 1 d . . .
H2 H 0.3670(9) 0.8200(2) 0.2653(10) Uani 0.034(3) 4 1 d . . .
H3 H 0.9003(8) 0.7803(2) 0.6973(10) Uani 0.032(2) 4 1 d . . .
N1 N 0.6954(3) 0.54111(7) 0.4805(3) Uani 0.0181(7) 4 1 d . . .
C7 C 0.7280(4) 0.52211(10) 0.6634(4) Uani 0.0153(9) 4 1 d . . .
C8 C 0.7790(4) 0.46686(10) 0.7114(4) Uani 0.0137(9) 4 1 d . . .
C9 C 0.8050(4) 0.43180(10) 0.5735(4) Uani 0.0143(9) 4 1 d . . .
C10 C 0.7767(4) 0.45190(10) 0.3921(4) Uani 0.0151(9) 4 1 d . . .
C11 C 0.7195(4) 0.50766(10) 0.3462(4) Uani 0.0160(9) 4 1 d . . .
C12 C 0.8087(5) 0.44666(12) 0.9147(5) Uani 0.0227(11) 4 1 d . . .
H1 H 0.6490(8) 0.5861(2) 0.4506(10) Uani 0.030(2) 4 1 d . . .
H4 H 0.6937(9) 0.5531(2) 0.7490(9) Uani 0.033(2) 4 1 d . . .
H5 H 0.8498(9) 0.3878(2) 0.6149(10) Uani 0.035(3) 4 1 d . . .
H6 H 0.7800(10) 0.4243(3) 0.2688(11) Uani 0.042(3) 4 1 d . . .
H7 H 0.7005(11) 0.5266(3) 0.2122(11) Uani 0.044(3) 4 1 d . . .
H8 H 0.9270(11) 0.4217(4) 0.9662(11) Uani 0.052(3) 4 1 d . . .
H9 H 0.8127(14) 0.4793(3) 1.0066(12) Uani 0.057(4) 4 1 d . . .
H10 H 0.7066(11) 0.4193(3) 0.9233(12) Uani 0.054(3) 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
? ? ? ? ? ? ? ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 11. STRUCTURE-FACTOR LIST


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1060087'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H10 Cl2 N2 O3'
_chemical_formula_weight         301.1
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
_cell_length_a                   7.808(2)
_cell_length_b                   23.582(7)
_cell_length_c                   7.432(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.81(2)
_cell_angle_gamma                90
_cell_volume                     1270.4(6)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    140
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.5739
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      140
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           ?
_diffrn_radiation_source         ?
_diffrn_radiation_wavelength     -1
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            6697
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         80.81
_diffrn_reflns_theta_full        12.5
_diffrn_measured_fraction_theta_max 0
_diffrn_measured_fraction_theta_full 0.92
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    0.0903
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          neutron

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             6695
_reflns_number_gt                5808
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_gt          0.1630
_refine_ls_R_factor_all          0.0884
_refine_ls_wR_factor_ref         0.1649
_refine_ls_goodness_of_fit_ref   2.81
_refine_ls_goodness_of_fit_gt    2.99
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         6695
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    refall
_refine_ls_shift/su_max          0.0072
_refine_ls_shift/su_mean         0.0005
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef       40.9(9)
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_length_neutron
_atom_type_scat_source
C 6.646 International_Tables_Vol_C
H -3.739 International_Tables_Vol_C
Cl 9.577 International_Tables_Vol_C
N 9.360 International_Tables_Vol_C
O 5.803 International_Tables_Vol_C

_computing_data_collection       unknown
_computing_cell_refinement       unknown
_computing_data_reduction        unknown
_computing_structure_solution    unknown
_computing_structure_refinement  ?
_computing_molecular_graphics    unknown
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5398(4) 0.63629(11) 0.3752(5) Uani 0.0229(11) 4 1 d . . .
O2 O 0.8288(5) 0.87952(12) 0.6493(6) Uani 0.0324(14) 4 1 d . . .
O3 O 0.5605(5) 0.89965(12) 0.4373(5) Uani 0.0272(13) 4 1 d . . .
N2 N 0.6800(3) 0.86480(7) 0.5273(3) Uani 0.0204(7) 4 1 d . . .
Cl1 Cl 0.2354(2) 0.70953(7) 0.1461(3) Uani 0.0227(7) 4 1 d . . .
Cl2 Cl 0.9072(2) 0.66073(7) 0.6832(3) Uani 0.0250(7) 4 1 d . . .
C1 C 0.5743(3) 0.68855(9) 0.4133(4) Uani 0.0157(9) 4 1 d . . .
C2 C 0.4438(3) 0.73145(9) 0.3165(4) Uani 0.0155(8) 4 1 d . . .
C3 C 0.4757(3) 0.78856(9) 0.3490(4) Uani 0.0168(9) 4 1 d . . .
C4 C 0.6440(3) 0.80580(9) 0.4906(4) Uani 0.0161(9) 4 1 d . . .
C5 C 0.7776(3) 0.76636(9) 0.5936(4) Uani 0.0165(9) 4 1 d . . .
C6 C 0.7423(3) 0.70969(9) 0.5546(4) Uani 0.0162(9) 4 1 d . . .
H2 H 0.3734(8) 0.8199(2) 0.2709(9) Uani 0.036(2) 4 1 d . . .
H3 H 0.9060(8) 0.7809(2) 0.7037(9) Uani 0.034(2) 4 1 d . . .
N1 N 0.6971(3) 0.54154(7) 0.4816(3) Uani 0.0212(7) 4 1 d . . .
C7 C 0.7263(3) 0.52245(9) 0.6608(4) Uani 0.0193(9) 4 1 d . . .
C8 C 0.7806(3) 0.46701(10) 0.7137(4) Uani 0.0177(9) 4 1 d . . .
C9 C 0.8051(3) 0.43162(10) 0.5764(4) Uani 0.0194(9) 4 1 d . . .
C10 C 0.7764(4) 0.45227(10) 0.3918(4) Uani 0.0212(10) 4 1 d . . .
C11 C 0.7210(4) 0.50817(10) 0.3476(4) Uani 0.0202(9) 4 1 d . . .
C12 C 0.8081(4) 0.44650(12) 0.9142(4) Uani 0.0265(11) 4 1 d . . .
H1 H 0.6453(8) 0.5867(2) 0.4435(10) Uani 0.037(2) 4 1 d . . .
H4 H 0.7005(9) 0.5532(2) 0.7587(10) Uani 0.043(3) 4 1 d . . .
H5 H 0.8457(9) 0.3881(2) 0.6127(10) Uani 0.040(2) 4 1 d . . .
H6 H 0.7898(9) 0.4250(3) 0.2809(10) Uani 0.044(3) 4 1 d . . .
H7 H 0.6948(9) 0.5276(3) 0.2069(10) Uani 0.045(3) 4 1 d . . .
H8 H 0.9316(13) 0.4221(4) 0.9750(13) Uani 0.071(4) 4 1 d . . .
H9 H 0.8162(14) 0.4814(3) 1.0087(12) Uani 0.069(4) 4 1 d . . .
H10 H 0.7007(11) 0.4188(4) 0.9110(13) Uani 0.071(4) 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
? ? ? ? ? ? ? ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 11. STRUCTURE-FACTOR LIST


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1060088'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H10 Cl2 N2 O3'
_chemical_formula_weight         301.1
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
_cell_length_a                   7.827(2)
_cell_length_b                   23.619(7)
_cell_length_c                   7.447(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.88(2)
_cell_angle_gamma                90
_cell_volume                     1277.6(7)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    170
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.5651
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      170
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           ?
_diffrn_radiation_source         ?
_diffrn_radiation_wavelength     -1
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            5943
_diffrn_reflns_theta_min         2.8
_diffrn_reflns_theta_max         73.36
_diffrn_reflns_theta_full        13.38
_diffrn_measured_fraction_theta_max 0
_diffrn_measured_fraction_theta_full 0.9
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    0.087
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       58
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          neutron

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             5943
_reflns_number_gt                5219
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0771
_refine_ls_wR_factor_gt          0.1575
_refine_ls_R_factor_all          0.0861
_refine_ls_wR_factor_ref         0.1591
_refine_ls_goodness_of_fit_ref   2.74
_refine_ls_goodness_of_fit_gt    2.90
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         5943
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    refall
_refine_ls_shift/su_max          0.0078
_refine_ls_shift/su_mean         0.0007
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef       45.0(10)
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_length_neutron
_atom_type_scat_source
C 6.646 International_Tables_Vol_C
H -3.739 International_Tables_Vol_C
Cl 9.577 International_Tables_Vol_C
N 9.360 International_Tables_Vol_C
O 5.803 International_Tables_Vol_C

_computing_data_collection       unknown
_computing_cell_refinement       unknown
_computing_data_reduction        unknown
_computing_structure_solution    unknown
_computing_structure_refinement  ?
_computing_molecular_graphics    unknown
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5415(4) 0.63642(12) 0.3765(5) Uani 0.0265(12) 4 1 d . . .
O2 O 0.8300(5) 0.87929(13) 0.6489(7) Uani 0.0395(16) 4 1 d . . .
O3 O 0.5617(5) 0.89943(13) 0.4376(6) Uani 0.0356(16) 4 1 d . . .
N2 N 0.6807(3) 0.86475(7) 0.5271(3) Uani 0.0252(8) 4 1 d . . .
Cl1 Cl 0.2374(3) 0.70969(8) 0.1472(3) Uani 0.0283(8) 4 1 d . . .
Cl2 Cl 0.9082(3) 0.66094(8) 0.6829(4) Uani 0.0318(8) 4 1 d . . .
C1 C 0.5764(3) 0.68880(10) 0.4135(4) Uani 0.0194(9) 4 1 d . . .
C2 C 0.4463(4) 0.73141(10) 0.3175(4) Uani 0.0199(10) 4 1 d . . .
C3 C 0.4779(4) 0.78857(10) 0.3495(4) Uani 0.0200(10) 4 1 d . . .
C4 C 0.6452(4) 0.80570(10) 0.4904(4) Uani 0.0197(10) 4 1 d . . .
C5 C 0.7790(4) 0.76638(10) 0.5937(4) Uani 0.0207(10) 4 1 d . . .
C6 C 0.7436(3) 0.70993(10) 0.5551(4) Uani 0.0202(10) 4 1 d . . .
H2 H 0.3745(9) 0.8198(2) 0.2730(10) Uani 0.041(3) 4 1 d . . .
H3 H 0.9084(8) 0.7813(2) 0.7036(10) Uani 0.041(3) 4 1 d . . .
N1 N 0.6983(3) 0.54175(7) 0.4820(3) Uani 0.0258(8) 4 1 d . . .
C7 C 0.7254(4) 0.52267(10) 0.6607(5) Uani 0.0238(11) 4 1 d . . .
C8 C 0.7793(4) 0.46721(10) 0.7135(4) Uani 0.0226(10) 4 1 d . . .
C9 C 0.8043(4) 0.43199(10) 0.5760(4) Uani 0.0234(10) 4 1 d . . .
C10 C 0.7761(4) 0.45276(11) 0.3930(4) Uani 0.0257(11) 4 1 d . . .
C11 C 0.7219(4) 0.50839(11) 0.3486(5) Uani 0.0253(11) 4 1 d . . .
C12 C 0.8057(5) 0.44668(15) 0.9131(5) Uani 0.0331(13) 4 1 d . . .
H1 H 0.6455(9) 0.5870(2) 0.4440(11) Uani 0.043(3) 4 1 d . . .
H4 H 0.7014(10) 0.5534(3) 0.7591(11) Uani 0.051(3) 4 1 d . . .
H5 H 0.8427(10) 0.3884(2) 0.6123(10) Uani 0.046(3) 4 1 d . . .
H6 H 0.7910(10) 0.4253(3) 0.2822(11) Uani 0.052(3) 4 1 d . . .
H7 H 0.6984(10) 0.5279(3) 0.2085(11) Uani 0.051(3) 4 1 d . . .
H8 H 0.9289(15) 0.4229(5) 0.9734(14) Uani 0.088(5) 4 1 d . . .
H9 H 0.8133(16) 0.4808(4) 1.0052(14) Uani 0.088(5) 4 1 d . . .
H10 H 0.6991(13) 0.4195(4) 0.9109(14) Uani 0.088(5) 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
? ? ? ? ? ? ? ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 11. STRUCTURE-FACTOR LIST


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1060089'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H10 Cl2 N2 O3'
_chemical_formula_weight         301.1
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
_cell_length_a                   7.846(2)
_cell_length_b                   23.647(7)
_cell_length_c                   7.460(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.01(2)
_cell_angle_gamma                90
_cell_volume                     1283.2(7)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    200
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.5582
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      200
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           ?
_diffrn_radiation_source         ?
_diffrn_radiation_wavelength     -1
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            5595
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         77.3
_diffrn_reflns_theta_full        11.53
_diffrn_measured_fraction_theta_max 0
_diffrn_measured_fraction_theta_full 0.93
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    0.0815
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -60
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          neutron

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             5593
_reflns_number_gt                4973
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_gt          0.1595
_refine_ls_R_factor_all          0.0850
_refine_ls_wR_factor_ref         0.1606
_refine_ls_goodness_of_fit_ref   2.88
_refine_ls_goodness_of_fit_gt    3.05
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         5593
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    refall
_refine_ls_shift/su_max          0.0322
_refine_ls_shift/su_mean         0.0046
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef       48.3(12)
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_length_neutron
_atom_type_scat_source
C 6.646 International_Tables_Vol_C
H -3.739 International_Tables_Vol_C
Cl 9.577 International_Tables_Vol_C
N 9.360 International_Tables_Vol_C
O 5.803 International_Tables_Vol_C

_computing_data_collection       unknown
_computing_cell_refinement       unknown
_computing_data_reduction        unknown
_computing_structure_solution    unknown
_computing_structure_refinement  ?
_computing_molecular_graphics    unknown
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5433(5) 0.63679(12) 0.3782(6) Uani 0.0324(14) 4 1 d . . .
O2 O 0.8300(5) 0.87949(14) 0.6475(7) Uani 0.0472(18) 4 1 d . . .
O3 O 0.5634(5) 0.89903(13) 0.4373(6) Uani 0.0412(17) 4 1 d . . .
N2 N 0.6816(3) 0.86461(8) 0.5269(4) Uani 0.0308(9) 4 1 d . . .
Cl1 Cl 0.2392(3) 0.70967(8) 0.1485(4) Uani 0.0343(9) 4 1 d . . .
Cl2 Cl 0.9095(3) 0.66115(8) 0.6837(4) Uani 0.0380(9) 4 1 d . . .
C1 C 0.5773(4) 0.68897(10) 0.4138(4) Uani 0.0223(10) 4 1 d . . .
C2 C 0.4469(4) 0.73150(10) 0.3178(4) Uani 0.0233(10) 4 1 d . . .
C3 C 0.4794(4) 0.78852(11) 0.3500(4) Uani 0.0238(11) 4 1 d . . .
C4 C 0.6472(4) 0.80568(10) 0.4909(4) Uani 0.0241(11) 4 1 d . . .
C5 C 0.7802(4) 0.76645(11) 0.5932(4) Uani 0.0244(11) 4 1 d . . .
C6 C 0.7452(4) 0.71011(11) 0.5555(4) Uani 0.0244(11) 4 1 d . . .
H2 H 0.3754(9) 0.8195(2) 0.2744(10) Uani 0.046(3) 4 1 d . . .
H3 H 0.9087(9) 0.7813(2) 0.7024(11) Uani 0.045(3) 4 1 d . . .
N1 N 0.6989(3) 0.54201(8) 0.4825(4) Uani 0.0309(9) 4 1 d . . .
C7 C 0.7258(4) 0.52296(11) 0.6612(5) Uani 0.0289(12) 4 1 d . . .
C8 C 0.7779(4) 0.46728(11) 0.7132(5) Uani 0.0272(11) 4 1 d . . .
C9 C 0.8027(4) 0.43233(11) 0.5752(5) Uani 0.0285(12) 4 1 d . . .
C10 C 0.7762(4) 0.45319(12) 0.3939(5) Uani 0.0299(12) 4 1 d . . .
C11 C 0.7239(4) 0.50863(11) 0.3509(5) Uani 0.0300(12) 4 1 d . . .
C12 C 0.8039(6) 0.44682(17) 0.9124(6) Uani 0.0396(16) 4 1 d . . .
H1 H 0.6461(9) 0.5871(3) 0.4446(11) Uani 0.051(3) 4 1 d . . .
H4 H 0.7001(10) 0.5535(3) 0.7569(11) Uani 0.056(3) 4 1 d . . .
H5 H 0.8420(10) 0.3887(2) 0.6106(11) Uani 0.054(3) 4 1 d . . .
H6 H 0.7912(11) 0.4252(3) 0.2842(11) Uani 0.063(4) 4 1 d . . .
H7 H 0.6992(11) 0.5284(3) 0.2107(12) Uani 0.061(4) 4 1 d . . .
H8 H 0.9236(17) 0.4240(5) 0.9743(16) Uani 0.104(6) 4 1 d . . .
H9 H 0.8106(18) 0.4804(5) 1.0029(15) Uani 0.105(6) 4 1 d . . .
H10 H 0.6967(14) 0.4196(5) 0.9079(15) Uani 0.097(5) 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
? ? ? ? ? ? ? ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 11. STRUCTURE-FACTOR LIST


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1060090'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H10 Cl2 N2 O3'
_chemical_formula_weight         301.1
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
_cell_length_a                   7.865(2)
_cell_length_b                   23.681(8)
_cell_length_c                   7.472(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.10(2)
_cell_angle_gamma                90
_cell_volume                     1289.6(7)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    230
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.5505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      230
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           ?
_diffrn_radiation_source         ?
_diffrn_radiation_wavelength     -1
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            4946
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         75.61
_diffrn_reflns_theta_full        13.61
_diffrn_measured_fraction_theta_max 0
_diffrn_measured_fraction_theta_full 0.89
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    0.0805
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       58
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          neutron

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             4943
_reflns_number_gt                4370
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0786
_refine_ls_wR_factor_gt          0.1665
_refine_ls_R_factor_all          0.0883
_refine_ls_wR_factor_ref         0.1708
_refine_ls_goodness_of_fit_ref   3.06
_refine_ls_goodness_of_fit_gt    3.18
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         4943
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    refall
_refine_ls_shift/su_max          0.0260
_refine_ls_shift/su_mean         0.0020
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef       46.7(13)
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_length_neutron
_atom_type_scat_source
C 6.646 International_Tables_Vol_C
H -3.739 International_Tables_Vol_C
Cl 9.577 International_Tables_Vol_C
N 9.360 International_Tables_Vol_C
O 5.803 International_Tables_Vol_C

_computing_data_collection       unknown
_computing_cell_refinement       unknown
_computing_data_reduction        unknown
_computing_structure_solution    unknown
_computing_structure_refinement  ?
_computing_molecular_graphics    unknown
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5448(5) 0.63689(15) 0.3785(7) Uani 0.0360(17) 4 1 d . . .
O2 O 0.8308(7) 0.87914(18) 0.6482(9) Uani 0.057(2) 4 1 d . . .
O3 O 0.5656(7) 0.89895(17) 0.4392(8) Uani 0.049(2) 4 1 d . . .
N2 N 0.6829(4) 0.86441(10) 0.5271(4) Uani 0.0357(12) 4 1 d . . .
Cl1 Cl 0.2417(3) 0.70958(10) 0.1493(4) Uani 0.0401(11) 4 1 d . . .
Cl2 Cl 0.9111(3) 0.66142(10) 0.6834(5) Uani 0.0440(12) 4 1 d . . .
C1 C 0.5783(4) 0.68912(12) 0.4140(5) Uani 0.0264(13) 4 1 d . . .
C2 C 0.4489(4) 0.73147(12) 0.3208(5) Uani 0.0249(12) 4 1 d . . .
C3 C 0.4800(5) 0.78837(13) 0.3512(5) Uani 0.0281(13) 4 1 d . . .
C4 C 0.6474(5) 0.80580(12) 0.4905(5) Uani 0.0284(14) 4 1 d . . .
C5 C 0.7819(5) 0.76649(13) 0.5929(5) Uani 0.0293(14) 4 1 d . . .
C6 C 0.7465(4) 0.71012(13) 0.5550(5) Uani 0.0284(13) 4 1 d . . .
H2 H 0.3799(11) 0.8191(3) 0.2720(12) Uani 0.051(3) 4 1 d . . .
H3 H 0.9083(10) 0.7814(3) 0.6993(13) Uani 0.051(3) 4 1 d . . .
N1 N 0.6992(3) 0.54215(10) 0.4849(4) Uani 0.0347(11) 4 1 d . . .
C7 C 0.7261(5) 0.52322(13) 0.6600(6) Uani 0.0327(15) 4 1 d . . .
C8 C 0.7772(5) 0.46777(13) 0.7138(6) Uani 0.0314(14) 4 1 d . . .
C9 C 0.8017(5) 0.43260(13) 0.5769(5) Uani 0.0306(14) 4 1 d . . .
C10 C 0.7761(5) 0.45339(14) 0.3929(6) Uani 0.0356(15) 4 1 d . . .
C11 C 0.7233(5) 0.50879(14) 0.3491(6) Uani 0.0356(16) 4 1 d . . .
C12 C 0.8045(8) 0.4467(2) 0.9118(7) Uani 0.046(2) 4 1 d . . .
H1 H 0.6473(11) 0.5876(3) 0.4435(13) Uani 0.055(4) 4 1 d . . .
H4 H 0.6980(12) 0.5535(3) 0.7552(14) Uani 0.063(4) 4 1 d . . .
H5 H 0.8417(12) 0.3889(3) 0.6137(13) Uani 0.061(4) 4 1 d . . .
H6 H 0.7895(14) 0.4264(4) 0.2841(15) Uani 0.073(5) 4 1 d . . .
H7 H 0.6986(14) 0.5284(3) 0.2097(14) Uani 0.068(4) 4 1 d . . .
H8 H 0.919(2) 0.4257(7) 0.9762(18) Uani 0.115(8) 4 1 d . . .
H9 H 0.807(2) 0.4816(6) 0.9961(17) Uani 0.113(8) 4 1 d . . .
H10 H 0.7024(18) 0.4193(6) 0.9102(17) Uani 0.116(7) 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
? ? ? ? ? ? ? ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 11. STRUCTURE-FACTOR LIST


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1060091'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H10 Cl2 N2 O3'
_chemical_formula_weight         301.1
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
_cell_length_a                   7.889(2)
_cell_length_b                   23.720(8)
_cell_length_c                   7.487(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.22(3)
_cell_angle_gamma                90
_cell_volume                     1297.0(8)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    260
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.5416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      260
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           ?
_diffrn_radiation_source         ?
_diffrn_radiation_wavelength     -1
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            4653
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         74.81
_diffrn_reflns_theta_full        12.98
_diffrn_measured_fraction_theta_max 0
_diffrn_measured_fraction_theta_full 0.89
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    0.0736
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          neutron

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             4651
_reflns_number_gt                4120
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0753
_refine_ls_wR_factor_gt          0.1633
_refine_ls_R_factor_all          0.0850
_refine_ls_wR_factor_ref         0.1652
_refine_ls_goodness_of_fit_ref   3.09
_refine_ls_goodness_of_fit_gt    3.26
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         4651
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    refall
_refine_ls_shift/su_max          0.0296
_refine_ls_shift/su_mean         0.0023
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef       50.6(14)
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_length_neutron
_atom_type_scat_source
C 6.646 International_Tables_Vol_C
H -3.739 International_Tables_Vol_C
Cl 9.577 International_Tables_Vol_C
N 9.360 International_Tables_Vol_C
O 5.803 International_Tables_Vol_C

_computing_data_collection       unknown
_computing_cell_refinement       unknown
_computing_data_reduction        unknown
_computing_structure_solution    unknown
_computing_structure_refinement  ?
_computing_molecular_graphics    unknown
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5448(5) 0.63700(15) 0.3806(7) Uani 0.0440(19) 4 1 d . . .
O2 O 0.8328(7) 0.87910(18) 0.6467(9) Uani 0.064(3) 4 1 d . . .
O3 O 0.5647(7) 0.89836(17) 0.4388(8) Uani 0.057(2) 4 1 d . . .
N2 N 0.6836(4) 0.86438(9) 0.5270(5) Uani 0.0428(13) 4 1 d . . .
Cl1 Cl 0.2427(3) 0.70959(10) 0.1514(4) Uani 0.0465(11) 4 1 d . . .
Cl2 Cl 0.9119(3) 0.66172(10) 0.6833(5) Uani 0.0510(12) 4 1 d . . .
C1 C 0.5791(4) 0.68907(12) 0.4154(5) Uani 0.0310(13) 4 1 d . . .
C2 C 0.4511(4) 0.73147(12) 0.3196(5) Uani 0.0308(13) 4 1 d . . .
C3 C 0.4822(5) 0.78814(13) 0.3512(6) Uani 0.0324(14) 4 1 d . . .
C4 C 0.6479(4) 0.80548(12) 0.4914(5) Uani 0.0328(14) 4 1 d . . .
C5 C 0.7830(5) 0.76664(13) 0.5934(6) Uani 0.0338(15) 4 1 d . . .
C6 C 0.7482(4) 0.71012(13) 0.5560(5) Uani 0.0327(14) 4 1 d . . .
H2 H 0.3766(10) 0.8192(3) 0.2767(12) Uani 0.058(4) 4 1 d . . .
H3 H 0.9098(12) 0.7812(3) 0.7010(13) Uani 0.060(4) 4 1 d . . .
N1 N 0.7005(3) 0.54250(10) 0.4839(4) Uani 0.0415(12) 4 1 d . . .
C7 C 0.7252(5) 0.52320(14) 0.6613(6) Uani 0.0391(16) 4 1 d . . .
C8 C 0.7758(5) 0.46782(13) 0.7124(5) Uani 0.0351(14) 4 1 d . . .
C9 C 0.8004(5) 0.43295(14) 0.5760(6) Uani 0.0398(15) 4 1 d . . .
C10 C 0.7762(5) 0.45384(14) 0.3964(6) Uani 0.0422(16) 4 1 d . . .
C11 C 0.7253(5) 0.50934(14) 0.3526(6) Uani 0.0413(17) 4 1 d . . .
C12 C 0.8020(8) 0.4472(2) 0.9115(7) Uani 0.053(2) 4 1 d . . .
H1 H 0.6494(10) 0.5881(3) 0.4458(13) Uani 0.059(4) 4 1 d . . .
H4 H 0.7008(13) 0.5535(3) 0.7571(13) Uani 0.075(5) 4 1 d . . .
H5 H 0.8396(12) 0.3895(3) 0.6118(13) Uani 0.067(4) 4 1 d . . .
H6 H 0.7907(14) 0.4264(4) 0.2872(13) Uani 0.082(5) 4 1 d . . .
H7 H 0.7052(14) 0.5289(3) 0.2139(15) Uani 0.079(5) 4 1 d . . .
H8 H 0.919(2) 0.4259(7) 0.974(2) Uani 0.133(8) 4 1 d . . .
H9 H 0.803(3) 0.4799(6) 1.004(2) Uani 0.150(10) 4 1 d . . .
H10 H 0.702(2) 0.4191(7) 0.9076(19) Uani 0.145(9) 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
? ? ? ? ? ? ? ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 11. STRUCTURE-FACTOR LIST


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1060092'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H10 Cl2 N2 O3'
_chemical_formula_weight         301.1
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
_cell_length_a                   7.911(2)
_cell_length_b                   23.760(8)
_cell_length_c                   7.502(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.33(2)
_cell_angle_gamma                90
_cell_volume                     1304.4(7)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    290
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.5329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      290
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           ?
_diffrn_radiation_source         ?
_diffrn_radiation_wavelength     -1
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            4056
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         68.84
_diffrn_reflns_theta_full        10.09
_diffrn_measured_fraction_theta_max 0
_diffrn_measured_fraction_theta_full 0.92
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          neutron

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             4056
_reflns_number_gt                3638
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0720
_refine_ls_wR_factor_gt          0.1510
_refine_ls_R_factor_all          0.0817
_refine_ls_wR_factor_ref         0.1525
_refine_ls_goodness_of_fit_ref   2.87
_refine_ls_goodness_of_fit_gt    3.01
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         4056
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    refall
_refine_ls_shift/su_max          0.0468
_refine_ls_shift/su_mean         0.0049
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_extinction_coef       53.4(15)
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_length_neutron
_atom_type_scat_source
C 6.646 International_Tables_Vol_C
H -3.739 International_Tables_Vol_C
Cl 9.577 International_Tables_Vol_C
N 9.360 International_Tables_Vol_C
O 5.803 International_Tables_Vol_C

_computing_data_collection       unknown
_computing_cell_refinement       unknown
_computing_data_reduction        unknown
_computing_structure_solution    unknown
_computing_structure_refinement  ?
_computing_molecular_graphics    unknown
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5477(6) 0.63725(16) 0.3798(7) Uani 0.050(2) 4 1 d . . .
O2 O 0.8318(8) 0.87889(19) 0.6468(10) Uani 0.074(3) 4 1 d . . .
O3 O 0.5664(7) 0.89802(19) 0.4388(9) Uani 0.066(3) 4 1 d . . .
N2 N 0.6842(4) 0.86406(10) 0.5263(5) Uani 0.0490(14) 4 1 d . . .
Cl1 Cl 0.2448(3) 0.70952(11) 0.1518(5) Uani 0.0536(12) 4 1 d . . .
Cl2 Cl 0.9130(4) 0.66207(10) 0.6837(5) Uani 0.0592(14) 4 1 d . . .
C1 C 0.5811(4) 0.68923(13) 0.4160(5) Uani 0.0360(14) 4 1 d . . .
C2 C 0.4517(4) 0.73127(13) 0.3207(5) Uani 0.0360(14) 4 1 d . . .
C3 C 0.4834(5) 0.78810(14) 0.3514(6) Uani 0.0366(15) 4 1 d . . .
C4 C 0.6496(5) 0.80540(13) 0.4907(6) Uani 0.0380(16) 4 1 d . . .
C5 C 0.7824(5) 0.76641(14) 0.5932(6) Uani 0.0381(16) 4 1 d . . .
C6 C 0.7492(4) 0.71018(13) 0.5557(5) Uani 0.0375(15) 4 1 d . . .
H2 H 0.3810(11) 0.8191(3) 0.2786(13) Uani 0.065(4) 4 1 d . . .
H3 H 0.9117(11) 0.7811(3) 0.7007(13) Uani 0.063(4) 4 1 d . . .
N1 N 0.7010(4) 0.54265(11) 0.4846(5) Uani 0.0473(13) 4 1 d . . .
C7 C 0.7259(5) 0.52335(15) 0.6619(6) Uani 0.0451(17) 4 1 d . . .
C8 C 0.7745(5) 0.46826(14) 0.7127(6) Uani 0.0416(16) 4 1 d . . .
C9 C 0.8002(5) 0.43348(15) 0.5762(6) Uani 0.0451(17) 4 1 d . . .
C10 C 0.7755(5) 0.45407(15) 0.3975(6) Uani 0.0471(18) 4 1 d . . .
C11 C 0.7261(6) 0.50963(15) 0.3540(7) Uani 0.0496(19) 4 1 d . . .
C12 C 0.8015(8) 0.4475(3) 0.9105(8) Uani 0.059(3) 4 1 d . . .
H1 H 0.6497(11) 0.5888(3) 0.4465(14) Uani 0.070(4) 4 1 d . . .
H4 H 0.6993(13) 0.5536(3) 0.7564(14) Uani 0.081(5) 4 1 d . . .
H5 H 0.8371(13) 0.3899(3) 0.6121(14) Uani 0.078(5) 4 1 d . . .
H6 H 0.7930(15) 0.4268(4) 0.2881(16) Uani 0.096(6) 4 1 d . . .
H7 H 0.7058(14) 0.5292(4) 0.2177(15) Uani 0.085(5) 4 1 d . . .
H8 H 0.911(2) 0.4258(8) 0.971(2) Uani 0.135(9) 4 1 d . . .
H9 H 0.799(3) 0.4789(7) 1.000(2) Uani 0.163(12) 4 1 d . . .
H10 H 0.697(2) 0.4192(6) 0.904(2) Uani 0.153(9) 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
? ? ? ? ? ? ? ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 11. STRUCTURE-FACTOR LIST


