# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1815110'
_audit_update_record             
;
2018-01-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 Cl2 O4, C5 H6 N2'
_chemical_formula_sum            'C11 H8 Cl2 N2 O4'
_chemical_formula_weight         303.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.711(2)
_cell_length_b                   14.834(5)
_cell_length_c                   12.391(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.88(3)
_cell_angle_gamma                90
_cell_volume                     1192(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    10753
_cell_measurement_theta_min      3.1344
_cell_measurement_theta_max      36.7245

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.556
_shelx_estimated_absorpt_T_min   0.772
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            4947
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.746
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.499
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2198
_reflns_number_gt                1943
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+1.1420P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2198
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.3980(3) -0.05823(13) 0.14642(16) 0.0134(4) Uani 1 1 d . . . . .
C3 C 0.2783(3) -0.03553(13) 0.04029(17) 0.0146(4) Uani 1 1 d . . . . .
H3 H 0.2166 -0.0826 -0.0091 0.018 Uiso 1 1 calc R U . . .
C5 C 0.3345(3) 0.11446(14) 0.07749(18) 0.0160(4) Uani 1 1 d . . . . .
H5 H 0.3163 0.1759 0.0554 0.019 Uiso 1 1 calc R U . . .
C6 C 0.4506(3) 0.09364(13) 0.18337(17) 0.0151(4) Uani 1 1 d . . . . .
H6 H 0.5092 0.1411 0.2328 0.018 Uiso 1 1 calc R U . . .
C21 C 0.4360(3) -0.15465(14) 0.18089(17) 0.0167(4) Uani 1 1 d . . . . .
H22 H 0.3173 -0.1912 0.1426 0.025 Uiso 1 1 calc R U . . .
H21 H 0.4558 -0.1597 0.2618 0.025 Uiso 1 1 calc R U . . .
H23 H 0.5598 -0.1762 0.1609 0.025 Uiso 1 1 calc R U . . .
N1 N 0.4831(3) 0.00768(11) 0.21857(14) 0.0137(4) Uani 1 1 d . . . . .
N2 N 0.2470(3) 0.05009(11) 0.00515(14) 0.0148(4) Uani 1 1 d . . . . .
H1 H 0.610(5) -0.026(2) 0.364(3) 0.045(9) Uiso 1 1 d . . . . .
H2 H 1.102(4) 0.084(2) 0.857(3) 0.042(9) Uiso 1 1 d . . . . .
C13 C 0.7603(3) 0.08319(13) 0.51415(16) 0.0120(4) Uani 1 1 d . . . . .
C16 C 0.9549(3) -0.02042(13) 0.70963(16) 0.0125(4) Uani 1 1 d . . . . .
O2 O 0.6603(2) -0.05938(9) 0.41972(12) 0.0149(3) Uani 1 1 d . . . . .
O5 O 1.0546(2) 0.12077(9) 0.80469(12) 0.0149(3) Uani 1 1 d . . . . .
Cl1 Cl 0.84849(8) -0.18177(3) 0.60980(4) 0.01590(15) Uani 1 1 d . . . . .
Cl2 Cl 0.87016(8) 0.24407(3) 0.61837(4) 0.01799(15) Uani 1 1 d . . . . .
C11 C 0.8489(3) -0.06596(13) 0.60635(16) 0.0125(4) Uani 1 1 d . . . . .
C12 C 0.7572(3) -0.01894(13) 0.51376(16) 0.0121(4) Uani 1 1 d . . . . .
C14 C 0.8668(3) 0.12819(13) 0.61745(17) 0.0132(4) Uani 1 1 d . . . . .
C15 C 0.9589(3) 0.08107(13) 0.70981(16) 0.0118(4) Uani 1 1 d . . . . .
O3 O 0.6740(2) 0.12243(9) 0.42871(11) 0.0154(3) Uani 1 1 d . . . . .
O6 O 1.0390(2) -0.05981(9) 0.79569(11) 0.0158(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 N1 1.349(3) . ?
C2 C3 1.395(3) . ?
C2 C21 1.496(3) . ?
C3 N2 1.342(3) . ?
C3 H3 0.9500 . ?
C5 N2 1.338(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 N1 1.347(3) . ?
C6 H6 0.9500 . ?
C21 H22 0.9800 . ?
C21 H21 0.9800 . ?
C21 H23 0.9800 . ?
C13 O3 1.217(2) . ?
C13 C14 1.458(3) . ?
C13 C12 1.515(3) . ?
C16 O6 1.220(2) . ?
C16 C11 1.460(3) . ?
C16 C15 1.506(3) . ?
O2 C12 1.323(2) . ?
O2 H1 0.85(3) . ?
O5 C15 1.324(2) . ?
O5 H2 0.84(3) . ?
Cl1 C11 1.718(2) . ?
Cl2 C14 1.719(2) . ?
C11 C12 1.349(3) . ?
C14 C15 1.348(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 C3 119.55(18) . . ?
N1 C2 C21 119.46(18) . . ?
C3 C2 C21 120.98(18) . . ?
N2 C3 C2 122.61(18) . . ?
N2 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
N2 C5 C6 121.44(19) . . ?
N2 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
N1 C6 C5 121.69(19) . . ?
N1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C2 C21 H22 109.5 . . ?
C2 C21 H21 109.5 . . ?
H22 C21 H21 109.5 . . ?
C2 C21 H23 109.5 . . ?
H22 C21 H23 109.5 . . ?
H21 C21 H23 109.5 . . ?
C6 N1 C2 117.76(17) . . ?
C5 N2 C3 116.93(18) . . ?
O3 C13 C14 124.16(18) . . ?
O3 C13 C12 118.20(17) . . ?
C14 C13 C12 117.64(17) . . ?
O6 C16 C11 123.81(18) . . ?
O6 C16 C15 118.27(17) . . ?
C11 C16 C15 117.92(16) . . ?
C12 O2 H1 117(2) . . ?
C15 O5 H2 114(2) . . ?
C12 C11 C16 121.29(18) . . ?
C12 C11 Cl1 122.34(15) . . ?
C16 C11 Cl1 116.36(14) . . ?
O2 C12 C11 121.88(18) . . ?
O2 C12 C13 117.34(17) . . ?
C11 C12 C13 120.77(17) . . ?
C15 C14 C13 121.51(18) . . ?
C15 C14 Cl2 120.70(15) . . ?
C13 C14 Cl2 117.79(15) . . ?
O5 C15 C14 122.36(18) . . ?
O5 C15 C16 116.77(17) . . ?
C14 C15 C16 120.87(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 1.5(3) . . . . ?
C21 C2 C3 N2 -177.61(19) . . . . ?
N2 C5 C6 N1 0.7(3) . . . . ?
C5 C6 N1 C2 0.1(3) . . . . ?
C3 C2 N1 C6 -1.1(3) . . . . ?
C21 C2 N1 C6 178.02(19) . . . . ?
C6 C5 N2 C3 -0.3(3) . . . . ?
C2 C3 N2 C5 -0.7(3) . . . . ?
O6 C16 C11 C12 179.53(19) . . . . ?
C15 C16 C11 C12 0.0(3) . . . . ?
O6 C16 C11 Cl1 -0.6(3) . . . . ?
C15 C16 C11 Cl1 179.88(14) . . . . ?
C16 C11 C12 O2 -179.88(18) . . . . ?
Cl1 C11 C12 O2 0.3(3) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
Cl1 C11 C12 C13 179.80(15) . . . . ?
O3 C13 C12 O2 0.1(3) . . . . ?
C14 C13 C12 O2 -179.97(17) . . . . ?
O3 C13 C12 C11 -179.44(19) . . . . ?
C14 C13 C12 C11 0.5(3) . . . . ?
O3 C13 C14 C15 179.6(2) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
O3 C13 C14 Cl2 0.1(3) . . . . ?
C12 C13 C14 Cl2 -179.83(14) . . . . ?
C13 C14 C15 O5 -179.30(18) . . . . ?
Cl2 C14 C15 O5 0.3(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
Cl2 C14 C15 C16 179.50(14) . . . . ?
O6 C16 C15 O5 -0.1(3) . . . . ?
C11 C16 C15 O5 179.49(17) . . . . ?
O6 C16 C15 C14 -179.35(19) . . . . ?
C11 C16 C15 C14 0.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O6 0.95 2.43 3.065(3) 124.1 1_454
C6 H6 O3 0.95 2.41 3.055(3) 124.8 .
O2 H1 N1 0.85(3) 1.85(3) 2.664(2) 159(3) .
O5 H2 N2 0.84(3) 1.91(3) 2.700(2) 155(3) 1_656
C21 H21 O2 0.98 2.56 3.276(3) 130.0 .
C21 H23 O5 0.98 2.64 3.414(3) 135.7 3_756

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1815112'
_audit_update_record             
;
2018-01-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H Cl2 O4, C7 H11 N2'
_chemical_formula_sum            'C13 H12 Cl2 N2 O4'
_chemical_formula_weight         331.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.463(3)
_cell_length_b                   8.976(3)
_cell_length_c                   10.962(4)
_cell_angle_alpha                95.57(2)
_cell_angle_beta                 111.82(3)
_cell_angle_gamma                109.33(2)
_cell_volume                     706(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5456
_cell_measurement_theta_min      2.9120
_cell_measurement_theta_max      36.6400

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.476
_shelx_estimated_absorpt_T_min   0.738
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            9923
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.929
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3238
_reflns_number_gt                2776
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0842P)²+0.0805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3238
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.52803(6) 0.93084(5) 0.35482(5) 0.03670(16) Uani 1 1 d . . . . .
Cl2 Cl 0.25325(7) 0.16098(5) 0.21443(5) 0.04071(17) Uani 1 1 d . . . . .
O2 O 0.54002(17) 0.71874(14) 0.13559(12) 0.0308(3) Uani 1 1 d . . . . .
H2 H 0.5338 0.6505 0.0740 0.046 Uiso 1 1 calc R U . . .
O3 O 0.42725(18) 0.39686(14) 0.08239(12) 0.0330(3) Uani 1 1 d . . . . .
O5 O 0.22708(19) 0.37478(15) 0.43008(13) 0.0370(3) Uani 1 1 d . . . . .
O6 O 0.32958(19) 0.69835(15) 0.47502(13) 0.0371(3) Uani 1 1 d . . . . .
C11 C 0.4512(2) 0.72210(19) 0.31358(17) 0.0261(3) Uani 1 1 d . . . . .
C12 C 0.4653(2) 0.64094(19) 0.21032(15) 0.0245(3) Uani 1 1 d . . . . .
C13 C 0.4011(2) 0.45771(19) 0.17615(15) 0.0251(3) Uani 1 1 d . . . . .
C14 C 0.3207(2) 0.37027(19) 0.25304(17) 0.0274(3) Uani 1 1 d . . . . .
C15 C 0.2972(2) 0.44578(19) 0.35812(16) 0.0269(3) Uani 1 1 d . . . . .
C16 C 0.3609(2) 0.63278(19) 0.38896(16) 0.0267(3) Uani 1 1 d . . . . .
N1 N 0.1751(2) 0.48834(18) 0.64123(15) 0.0299(3) Uani 1 1 d . . . . .
H1 H 0.208(3) 0.468(3) 0.568(3) 0.061(7) Uiso 1 1 d . . . . .
N2 N 0.12008(19) 0.55507(17) 0.86610(14) 0.0305(3) Uani 1 1 d . . . . .
C2 C 0.0987(2) 0.3627(2) 0.68693(17) 0.0298(3) Uani 1 1 d . . . . .
C21 C 0.0435(3) 0.1926(2) 0.6122(2) 0.0384(4) Uani 1 1 d . . . . .
H21 H 0.0795 0.1949 0.5369 0.058 Uiso 1 1 calc R U . . .
H22 H -0.0912 0.1338 0.5764 0.058 Uiso 1 1 calc R U . . .
H23 H 0.1057 0.1371 0.6741 0.058 Uiso 1 1 calc R U . . .
C3 C 0.0735(2) 0.4014(2) 0.80440(17) 0.0294(3) Uani 1 1 d . . . . .
C31 C -0.0064(3) 0.2688(2) 0.8641(2) 0.0387(4) Uani 1 1 d . . . . .
H31 H 0.0811 0.2175 0.9003 0.058 Uiso 1 1 calc R U . . .
H32 H -0.1236 0.1868 0.7935 0.058 Uiso 1 1 calc R U . . .
H33 H -0.0289 0.3155 0.9375 0.058 Uiso 1 1 calc R U . . .
C5 C 0.1944(2) 0.6779(2) 0.81616(17) 0.0302(4) Uani 1 1 d . . . . .
C51 C 0.2420(3) 0.8480(2) 0.8863(2) 0.0414(4) Uani 1 1 d . . . . .
H51 H 0.1286 0.8606 0.8795 0.062 Uiso 1 1 calc R U . . .
H52 H 0.3021 0.9245 0.8434 0.062 Uiso 1 1 calc R U . . .
H53 H 0.3267 0.8708 0.9821 0.062 Uiso 1 1 calc R U . . .
C6 C 0.2239(2) 0.6434(2) 0.70252(17) 0.0321(4) Uani 1 1 d . . . . .
H6 H 0.2785 0.7295 0.6682 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.7171(17) . ?
Cl2 C14 1.7292(17) . ?
O2 C12 1.3276(19) . ?
O2 H2 0.8400 . ?
O3 C13 1.242(2) . ?
O5 C15 1.255(2) . ?
O6 C16 1.220(2) . ?
C11 C12 1.351(2) . ?
C11 C16 1.450(2) . ?
C12 C13 1.509(2) . ?
C13 C14 1.411(2) . ?
C14 C15 1.391(2) . ?
C15 C16 1.542(2) . ?
N1 C6 1.338(2) . ?
N1 C2 1.345(2) . ?
N1 H1 0.96(3) . ?
N2 C3 1.333(2) . ?
N2 C5 1.351(2) . ?
C2 C3 1.411(2) . ?
C2 C21 1.490(2) . ?
C21 H21 0.9800 . ?
C21 H22 0.9800 . ?
C21 H23 0.9800 . ?
C3 C31 1.500(2) . ?
C31 H31 0.9800 . ?
C31 H32 0.9800 . ?
C31 H33 0.9800 . ?
C5 C6 1.385(2) . ?
C5 C51 1.489(3) . ?
C51 H51 0.9800 . ?
C51 H52 0.9800 . ?
C51 H53 0.9800 . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 H2 109.5 . . ?
C12 C11 C16 120.13(14) . . ?
C12 C11 Cl1 121.87(13) . . ?
C16 C11 Cl1 117.93(12) . . ?
O2 C12 C11 121.63(15) . . ?
O2 C12 C13 116.62(13) . . ?
C11 C12 C13 121.73(14) . . ?
O3 C13 C14 125.45(15) . . ?
O3 C13 C12 116.10(14) . . ?
C14 C13 C12 118.45(14) . . ?
C15 C14 C13 122.74(14) . . ?
C15 C14 Cl2 119.71(12) . . ?
C13 C14 Cl2 117.54(12) . . ?
O5 C15 C14 125.66(15) . . ?
O5 C15 C16 116.73(14) . . ?
C14 C15 C16 117.61(14) . . ?
O6 C16 C11 123.03(15) . . ?
O6 C16 C15 117.81(15) . . ?
C11 C16 C15 119.15(14) . . ?
C6 N1 C2 122.15(15) . . ?
C6 N1 H1 118.1(15) . . ?
C2 N1 H1 119.4(15) . . ?
C3 N2 C5 119.64(15) . . ?
N1 C2 C3 116.89(16) . . ?
N1 C2 C21 119.54(16) . . ?
C3 C2 C21 123.56(16) . . ?
C2 C21 H21 109.5 . . ?
C2 C21 H22 109.5 . . ?
H21 C21 H22 109.5 . . ?
C2 C21 H23 109.5 . . ?
H21 C21 H23 109.5 . . ?
H22 C21 H23 109.5 . . ?
N2 C3 C2 121.71(15) . . ?
N2 C3 C31 117.95(15) . . ?
C2 C3 C31 120.34(16) . . ?
C3 C31 H31 109.5 . . ?
C3 C31 H32 109.5 . . ?
H31 C31 H32 109.5 . . ?
C3 C31 H33 109.5 . . ?
H31 C31 H33 109.5 . . ?
H32 C31 H33 109.5 . . ?
N2 C5 C6 119.77(16) . . ?
N2 C5 C51 118.23(16) . . ?
C6 C5 C51 121.99(16) . . ?
C5 C51 H51 109.5 . . ?
C5 C51 H52 109.5 . . ?
H51 C51 H52 109.5 . . ?
C5 C51 H53 109.5 . . ?
H51 C51 H53 109.5 . . ?
H52 C51 H53 109.5 . . ?
N1 C6 C5 119.81(16) . . ?
N1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 O2 177.11(15) . . . . ?
Cl1 C11 C12 O2 0.2(2) . . . . ?
C16 C11 C12 C13 -4.4(2) . . . . ?
Cl1 C11 C12 C13 178.73(11) . . . . ?
O2 C12 C13 O3 1.2(2) . . . . ?
C11 C12 C13 O3 -177.41(15) . . . . ?
O2 C12 C13 C14 -179.95(14) . . . . ?
C11 C12 C13 C14 1.5(2) . . . . ?
O3 C13 C14 C15 179.18(16) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
O3 C13 C14 Cl2 0.2(2) . . . . ?
C12 C13 C14 Cl2 -178.55(11) . . . . ?
C13 C14 C15 O5 -179.88(16) . . . . ?
Cl2 C14 C15 O5 -0.9(2) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
Cl2 C14 C15 C16 179.59(11) . . . . ?
C12 C11 C16 O6 -173.37(16) . . . . ?
Cl1 C11 C16 O6 3.6(2) . . . . ?
C12 C11 C16 C15 5.4(2) . . . . ?
Cl1 C11 C16 C15 -177.64(11) . . . . ?
O5 C15 C16 O6 -4.2(2) . . . . ?
C14 C15 C16 O6 175.32(15) . . . . ?
O5 C15 C16 C11 177.01(15) . . . . ?
C14 C15 C16 C11 -3.5(2) . . . . ?
C6 N1 C2 C3 -0.6(2) . . . . ?
C6 N1 C2 C21 178.58(16) . . . . ?
C5 N2 C3 C2 -0.4(3) . . . . ?
C5 N2 C3 C31 179.27(16) . . . . ?
N1 C2 C3 N2 1.1(2) . . . . ?
C21 C2 C3 N2 -178.05(16) . . . . ?
N1 C2 C3 C31 -178.52(16) . . . . ?
C21 C2 C3 C31 2.3(3) . . . . ?
C3 N2 C5 C6 -0.9(3) . . . . ?
C3 N2 C5 C51 179.04(16) . . . . ?
C2 N1 C6 C5 -0.6(3) . . . . ?
N2 C5 C6 N1 1.3(3) . . . . ?
C51 C5 C6 N1 -178.55(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.84 1.90 2.6579(18) 149.9 2_665
N1 H1 O5 0.96(3) 1.74(3) 2.681(2) 164(2) .
C6 H6 O6 0.95 2.32 2.978(2) 125.7 .
C21 H21 O5 0.98 2.38 3.215(2) 142.8 .
C31 H32 Cl2 0.98 2.93 3.560(2) 123.3 2_556
C51 H53 O2 0.98 2.79 3.550(3) 135.1 1_556
C31 H33 N2 0.98 2.82 3.793(3) 175.8 2_567

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1815114'
_audit_update_record             
;
2018-01-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H Br2 O4, C7 H11 N2'
_chemical_formula_sum            'C13 H12 Br2 N2 O4'
_chemical_formula_weight         420.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.450(4)
_cell_length_b                   9.153(2)
_cell_length_c                   10.952(4)
_cell_angle_alpha                67.50(3)
_cell_angle_beta                 67.45(2)
_cell_angle_gamma                72.56(3)
_cell_volume                     711(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7675
_cell_measurement_theta_min      3.6830
_cell_measurement_theta_max      36.5670

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    5.717
_shelx_estimated_absorpt_T_min   0.341
_shelx_estimated_absorpt_T_max   0.547
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.431
_exptl_absorpt_correction_T_max  0.644
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            9479
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.844
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3247
_reflns_number_gt                2920
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+0.1294P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3247
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3233(3) 0.4740(2) 0.6507(2) 0.0160(4) Uani 1 1 d . . . . .
H1 H 0.305(4) 0.452(4) 0.582(4) 0.038(9) Uiso 1 1 d . . . . .
N2 N 0.3947(2) 0.5396(2) 0.8449(2) 0.0175(4) Uani 1 1 d . . . . .
C5 C 0.3563(3) 0.6594(3) 0.7357(2) 0.0169(4) Uani 1 1 d . . . . .
C2 C 0.3644(3) 0.3503(3) 0.7562(2) 0.0161(4) Uani 1 1 d . . . . .
C3 C 0.3976(3) 0.3881(3) 0.8566(2) 0.0171(4) Uani 1 1 d . . . . .
C6 C 0.3183(3) 0.6273(3) 0.6379(2) 0.0169(4) Uani 1 1 d . . . . .
H6 H 0.2888 0.7124 0.5623 0.020 Uiso 1 1 calc R U . . .
C51 C 0.3582(3) 0.8275(3) 0.7241(3) 0.0210(5) Uani 1 1 d . . . . .
H51 H 0.4787 0.8414 0.6974 0.031 Uiso 1 1 calc R U . . .
H52 H 0.2928 0.8470 0.8138 0.031 Uiso 1 1 calc R U . . .
H53 H 0.3042 0.9040 0.6536 0.031 Uiso 1 1 calc R U . . .
C31 C 0.4390(3) 0.2578(3) 0.9798(2) 0.0209(5) Uani 1 1 d . . . . .
H31 H 0.3366 0.2076 1.0392 0.031 Uiso 1 1 calc R U . . .
H32 H 0.4711 0.3040 1.0324 0.031 Uiso 1 1 calc R U . . .
H33 H 0.5364 0.1766 0.9482 0.031 Uiso 1 1 calc R U . . .
C21 C 0.3751(3) 0.1824(3) 0.7607(2) 0.0206(5) Uani 1 1 d . . . . .
H21 H 0.3437 0.1852 0.6825 0.031 Uiso 1 1 calc R U . . .
H22 H 0.2944 0.1289 0.8480 0.031 Uiso 1 1 calc R U . . .
H23 H 0.4942 0.1232 0.7547 0.031 Uiso 1 1 calc R U . . .
Br1 Br 0.09016(3) 0.93354(2) 0.15339(2) 0.01795(9) Uani 1 1 d . . . . .
Br2 Br 0.14261(3) 0.13865(2) 0.38666(2) 0.01837(9) Uani 1 1 d . . . . .
O3 O 0.0452(2) 0.39388(19) 0.13253(17) 0.0171(3) Uani 1 1 d . . . . .
O2 O 0.0243(2) 0.70798(19) 0.03622(17) 0.0171(3) Uani 1 1 d . . . . .
H2 H 0.0021 0.6416 0.0118 0.026 Uiso 1 1 calc R U . . .
O5 O 0.2378(2) 0.3631(2) 0.49451(17) 0.0198(3) Uani 1 1 d . . . . .
O6 O 0.2375(2) 0.6791(2) 0.38378(17) 0.0200(3) Uani 1 1 d . . . . .
C14 C 0.1432(3) 0.3618(3) 0.3185(2) 0.0147(4) Uani 1 1 d . . . . .
C15 C 0.1895(3) 0.4334(3) 0.3884(2) 0.0147(4) Uani 1 1 d . . . . .
C16 C 0.1834(3) 0.6177(3) 0.3297(2) 0.0151(4) Uani 1 1 d . . . . .
C12 C 0.0795(3) 0.6308(3) 0.1470(2) 0.0137(4) Uani 1 1 d . . . . .
C11 C 0.1165(3) 0.7087(3) 0.2126(2) 0.0148(4) Uani 1 1 d . . . . .
C13 C 0.0902(3) 0.4499(3) 0.1986(2) 0.0141(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.345(3) . ?
N1 C6 1.345(3) . ?
N1 H1 0.92(3) . ?
N2 C3 1.337(3) . ?
N2 C5 1.348(3) . ?
C5 C6 1.378(3) . ?
C5 C51 1.499(3) . ?
C2 C3 1.411(3) . ?
C2 C21 1.494(3) . ?
C3 C31 1.498(3) . ?
C6 H6 0.9500 . ?
C51 H51 0.9800 . ?
C51 H52 0.9800 . ?
C51 H53 0.9800 . ?
C31 H31 0.9800 . ?
C31 H32 0.9800 . ?
C31 H33 0.9800 . ?
C21 H21 0.9800 . ?
C21 H22 0.9800 . ?
C21 H23 0.9800 . ?
Br1 C11 1.876(2) . ?
Br2 C14 1.888(2) . ?
O3 C13 1.243(3) . ?
O2 C12 1.330(3) . ?
O2 H2 0.8400 . ?
O5 C15 1.251(3) . ?
O6 C16 1.222(3) . ?
C14 C15 1.391(3) . ?
C14 C13 1.413(3) . ?
C15 C16 1.551(3) . ?
C16 C11 1.454(3) . ?
C12 C11 1.348(3) . ?
C12 C13 1.517(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 122.1(2) . . ?
C2 N1 H1 119(2) . . ?
C6 N1 H1 119(2) . . ?
C3 N2 C5 119.2(2) . . ?
N2 C5 C6 120.8(2) . . ?
N2 C5 C51 117.7(2) . . ?
C6 C5 C51 121.5(2) . . ?
N1 C2 C3 117.1(2) . . ?
N1 C2 C21 119.3(2) . . ?
C3 C2 C21 123.6(2) . . ?
N2 C3 C2 121.6(2) . . ?
N2 C3 C31 117.9(2) . . ?
C2 C3 C31 120.5(2) . . ?
N1 C6 C5 119.2(2) . . ?
N1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C5 C51 H51 109.5 . . ?
C5 C51 H52 109.5 . . ?
H51 C51 H52 109.5 . . ?
C5 C51 H53 109.5 . . ?
H51 C51 H53 109.5 . . ?
H52 C51 H53 109.5 . . ?
C3 C31 H31 109.5 . . ?
C3 C31 H32 109.5 . . ?
H31 C31 H32 109.5 . . ?
C3 C31 H33 109.5 . . ?
H31 C31 H33 109.5 . . ?
H32 C31 H33 109.5 . . ?
C2 C21 H21 109.5 . . ?
C2 C21 H22 109.5 . . ?
H21 C21 H22 109.5 . . ?
C2 C21 H23 109.5 . . ?
H21 C21 H23 109.5 . . ?
H22 C21 H23 109.5 . . ?
C12 O2 H2 109.5 . . ?
C15 C14 C13 122.8(2) . . ?
C15 C14 Br2 119.89(16) . . ?
C13 C14 Br2 117.25(17) . . ?
O5 C15 C14 126.3(2) . . ?
O5 C15 C16 116.1(2) . . ?
C14 C15 C16 117.66(19) . . ?
O6 C16 C11 123.2(2) . . ?
O6 C16 C15 117.9(2) . . ?
C11 C16 C15 118.95(19) . . ?
O2 C12 C11 122.3(2) . . ?
O2 C12 C13 115.48(19) . . ?
C11 C12 C13 122.2(2) . . ?
C12 C11 C16 119.9(2) . . ?
C12 C11 Br1 121.64(17) . . ?
C16 C11 Br1 118.43(17) . . ?
O3 C13 C14 126.1(2) . . ?
O3 C13 C12 115.8(2) . . ?
C14 C13 C12 118.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C5 C6 0.8(3) . . . . ?
C3 N2 C5 C51 -178.6(2) . . . . ?
C6 N1 C2 C3 1.8(3) . . . . ?
C6 N1 C2 C21 -177.4(2) . . . . ?
C5 N2 C3 C2 1.1(3) . . . . ?
C5 N2 C3 C31 -179.5(2) . . . . ?
N1 C2 C3 N2 -2.4(3) . . . . ?
C21 C2 C3 N2 176.7(2) . . . . ?
N1 C2 C3 C31 178.2(2) . . . . ?
C21 C2 C3 C31 -2.7(3) . . . . ?
C2 N1 C6 C5 0.0(3) . . . . ?
N2 C5 C6 N1 -1.4(3) . . . . ?
C51 C5 C6 N1 178.0(2) . . . . ?
C13 C14 C15 O5 -179.8(2) . . . . ?
Br2 C14 C15 O5 2.2(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
Br2 C14 C15 C16 -178.58(15) . . . . ?
O5 C15 C16 O6 5.2(3) . . . . ?
C14 C15 C16 O6 -174.1(2) . . . . ?
O5 C15 C16 C11 -175.6(2) . . . . ?
C14 C15 C16 C11 5.1(3) . . . . ?
O2 C12 C11 C16 -177.4(2) . . . . ?
C13 C12 C11 C16 5.4(3) . . . . ?
O2 C12 C11 Br1 0.8(3) . . . . ?
C13 C12 C11 Br1 -176.43(16) . . . . ?
O6 C16 C11 C12 171.7(2) . . . . ?
C15 C16 C11 C12 -7.5(3) . . . . ?
O6 C16 C11 Br1 -6.6(3) . . . . ?
C15 C16 C11 Br1 174.31(15) . . . . ?
C15 C14 C13 O3 -179.0(2) . . . . ?
Br2 C14 C13 O3 -1.0(3) . . . . ?
C15 C14 C13 C12 -1.6(3) . . . . ?
Br2 C14 C13 C12 176.45(15) . . . . ?
O2 C12 C13 O3 -0.5(3) . . . . ?
C11 C12 C13 O3 176.9(2) . . . . ?
O2 C12 C13 C14 -178.20(19) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O5 0.92(3) 1.79(4) 2.682(3) 162(3) .
O2 H2 O3 0.84 1.93 2.666(2) 145.8 2_565
C6 H6 O6 0.95 2.30 2.947(3) 124.8 .
C21 H21 O5 0.98 2.38 3.215(3) 142.7 .
C21 H22 O2 0.98 2.74 3.356(3) 121.3 2_566
C21 H23 O6 0.98 2.90 3.436(3) 115.0 2_666
C51 H52 O2 0.98 2.80 3.526(3) 131.8 1_556

_refine_diff_density_max         0.710
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1815111'
_audit_update_record             
;
2018-01-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 Br2 O4, C5 H6 N2'
_chemical_formula_sum            'C11 H8 Br2 N2 O4'
_chemical_formula_weight         392.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   20.001(2)
_cell_length_b                   4.845(4)
_cell_length_c                   16.024(4)
_cell_angle_alpha                90
_cell_angle_beta                 125.35(3)
_cell_angle_gamma                90
_cell_volume                     1266(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3553
_cell_measurement_theta_min      3.1070
_cell_measurement_theta_max      36.3930

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.056
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    6.412
_shelx_estimated_absorpt_T_min   0.446
_shelx_estimated_absorpt_T_max   0.784
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.569
_exptl_absorpt_correction_T_max  0.817
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            5110
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.117
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1451
_reflns_number_gt                1341
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+5.4830P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1451
_refine_ls_number_parameters     93
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_restrained_S_all      1.228
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.21442(2) 0.11998(8) 0.30382(3) 0.01742(15) Uani 1 1 d . . . . .
O2 O 0.12309(18) 0.1268(6) 0.4049(2) 0.0197(6) Uani 1 1 d . . . . .
H1 H 0.1042 0.1380 0.4399 0.030 Uiso 1 1 calc R U . . .
O3 O 0.15464(17) -0.1828(5) 0.5642(2) 0.0173(6) Uani 1 1 d . . . . .
C11 C 0.2321(2) -0.0869(7) 0.4143(3) 0.0153(8) Uani 1 1 d . . . . .
C13 C 0.2003(2) -0.2179(7) 0.5382(3) 0.0135(7) Uani 1 1 d . . . . .
C12 C 0.1845(2) -0.0503(7) 0.4481(3) 0.0149(8) Uani 1 1 d . . . . .
N1 N 0.0384(2) 0.3244(7) 0.4713(3) 0.0186(7) Uani 1 1 d . . . . .
C3 C 0.0509(2) 0.3027(8) 0.5621(3) 0.0182(8) Uani 1 1 d . . . . .
H3 H 0.0869 0.1638 0.6082 0.022 Uiso 1 1 calc R U . . .
C2 C -0.0127(3) 0.5224(9) 0.4083(3) 0.0194(8) Uani 1 1 d . . . A 1
C21 C -0.0227(5) 0.5700(18) 0.3094(6) 0.0225(18) Uani 0.5 1 d . . P A 1
H21A H 0.0308 0.6095 0.3231 0.034 Uiso 0.5 1 calc R U P A 1
H21B H -0.0595 0.7270 0.2737 0.034 Uiso 0.5 1 calc R U P A 1
H21C H -0.0461 0.4046 0.2666 0.034 Uiso 0.5 1 calc R U P A 1
H2 H -0.0226 0.5444 0.3444 0.027 Uiso 0.5 1 d . U P B 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.881(4) . ?
O2 C12 1.319(5) . ?
O2 H1 0.8400 . ?
O3 C13 1.215(5) . ?
C11 C12 1.353(5) . ?
C11 C13 1.453(5) 7_546 ?
C13 C11 1.453(5) 7_546 ?
C13 C12 1.521(5) . ?
N1 C3 1.331(5) . ?
N1 C2 1.338(5) . ?
C3 C2 1.395(6) 5_566 ?
C3 H3 0.9500 . ?
C2 C3 1.395(6) 5_566 ?
C2 C21 1.496(9) . ?
C2 H2 0.9304 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 H2 0.5723 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 H1 109.5 . . ?
C12 C11 C13 122.2(3) . 7_546 ?
C12 C11 Br1 121.0(3) . . ?
C13 C11 Br1 116.8(3) 7_546 . ?
O3 C13 C11 124.6(4) . 7_546 ?
O3 C13 C12 117.7(3) . . ?
C11 C13 C12 117.7(3) 7_546 . ?
O2 C12 C11 122.1(4) . . ?
O2 C12 C13 117.7(3) . . ?
C11 C12 C13 120.1(3) . . ?
C3 N1 C2 117.3(3) . . ?
N1 C3 C2 122.1(4) . 5_566 ?
N1 C3 H3 119.0 . . ?
C2 C3 H3 119.0 5_566 . ?
N1 C2 C3 120.6(4) . 5_566 ?
N1 C2 C21 119.0(5) . . ?
C3 C2 C21 120.1(5) 5_566 . ?
N1 C2 H2 119.7 . . ?
C3 C2 H2 119.6 5_566 . ?
C21 C2 H2 4.4 . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 C21 H2 7.1 . . ?
H21A C21 H2 116.0 . . ?
H21B C21 H2 108.4 . . ?
H21C C21 H2 103.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C11 C12 O2 -180.0(4) 7_546 . . . ?
Br1 C11 C12 O2 1.2(5) . . . . ?
C13 C11 C12 C13 -0.6(6) 7_546 . . . ?
Br1 C11 C12 C13 -179.4(3) . . . . ?
O3 C13 C12 O2 1.3(5) . . . . ?
C11 C13 C12 O2 180.0(3) 7_546 . . . ?
O3 C13 C12 C11 -178.2(4) . . . . ?
C11 C13 C12 C11 0.5(6) 7_546 . . . ?
C2 N1 C3 C2 0.0(7) . . . 5_566 ?
C3 N1 C2 C3 0.0(7) . . . 5_566 ?
C3 N1 C2 C21 174.7(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H1 N1 0.84 1.89 2.645(4) 149.4 .
C3 H3 O3 0.95 2.50 3.124(5) 123.2 .
C21 H21C O2 0.98 2.62 3.530(9) 155.4 2

_refine_diff_density_max         0.522
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.134

####################################################################### 
# 
# 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_3ba
_database_code_depnum_ccdc_archive 'CCDC 1815113'
_audit_update_record             
;
2018-01-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H Cl2 O4, C7 H11 N2'
_chemical_formula_sum            'C13 H12 Cl2 N2 O4'
_chemical_formula_weight         331.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.379(7)
_cell_length_b                   14.992(3)
_cell_length_c                   16.043(4)
_cell_angle_alpha                113.90(4)
_cell_angle_beta                 103.69(3)
_cell_angle_gamma                98.24(2)
_cell_volume                     2752(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7338
_cell_measurement_theta_min      3.0510
_cell_measurement_theta_max      36.4210

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.720
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.489
_shelx_estimated_absorpt_T_min   0.720
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            25077
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.938
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.499
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10236
_reflns_number_gt                6857
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0771P)²+0.7576P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10236
_refine_ls_number_parameters     773
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1562
_refine_ls_wR_factor_gt          0.1414
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 0.56110(6) 0.19428(6) 0.44475(6) 0.0214(2) Uani 1 1 d . . . . .
Cl2A Cl 0.40350(7) 0.50397(6) 0.75829(6) 0.0226(2) Uani 1 1 d . . . . .
O2A O 0.33668(17) 0.19886(17) 0.43382(16) 0.0186(5) Uani 1 1 d . . . . .
H2A H 0.2760 0.2053 0.4364 0.028 Uiso 1 1 calc R U . . .
O3A O 0.27381(17) 0.33311(17) 0.56477(17) 0.0218(5) Uani 1 1 d . . . . .
O5A O 0.63007(18) 0.49955(17) 0.76794(16) 0.0207(5) Uani 1 1 d . . . . .
O6A O 0.69211(17) 0.37385(17) 0.62823(17) 0.0207(5) Uani 1 1 d . . . . .
C11A C 0.5159(3) 0.2781(2) 0.5277(2) 0.0157(7) Uani 1 1 d . . . . .
C12A C 0.4110(3) 0.2710(2) 0.5131(2) 0.0166(7) Uani 1 1 d . . . . .
C13A C 0.3727(3) 0.3460(2) 0.5868(2) 0.0149(7) Uani 1 1 d . . . . .
C14A C 0.4484(3) 0.4218(3) 0.6731(2) 0.0174(7) Uani 1 1 d . . . . .
C15A C 0.5586(3) 0.4336(2) 0.6926(2) 0.0163(7) Uani 1 1 d . . . . .
C16A C 0.5956(3) 0.3597(2) 0.6148(2) 0.0158(7) Uani 1 1 d . . . . .
Cl1B Cl 0.15955(6) -0.26083(6) 0.47694(6) 0.0209(2) Uani 1 1 d . . . . .
Cl2B Cl 0.00246(7) 0.04017(6) 0.79720(6) 0.0219(2) Uani 1 1 d . . . . .
O2B O -0.06124(17) -0.27939(17) 0.48542(17) 0.0203(5) Uani 1 1 d . . . . .
H2B H -0.1225 -0.2736 0.4866 0.030 Uiso 1 1 calc R U . . .
O3B O -0.12385(17) -0.15335(17) 0.62243(17) 0.0204(5) Uani 1 1 d . . . . .
O5B O 0.22839(18) 0.05816(17) 0.79014(17) 0.0216(5) Uani 1 1 d . . . . .
O6B O 0.28698(18) -0.06695(17) 0.64747(17) 0.0214(5) Uani 1 1 d . . . . .
C11B C 0.1160(2) -0.1805(2) 0.5634(2) 0.0147(7) Uani 1 1 d . . . . .
C12B C 0.0117(2) -0.1984(2) 0.5576(2) 0.0157(7) Uani 1 1 d . . . . .
C13B C -0.0266(3) -0.1280(2) 0.6336(2) 0.0181(7) Uani 1 1 d . . . . .
C14B C 0.0483(3) -0.0404(2) 0.7113(2) 0.0158(7) Uani 1 1 d . . . . .
C15B C 0.1565(3) -0.0175(2) 0.7216(2) 0.0172(7) Uani 1 1 d . . . . .
C16B C 0.1927(3) -0.0906(2) 0.6417(2) 0.0153(7) Uani 1 1 d . . . . .
Cl1C Cl 0.86334(6) -0.03649(6) -0.03439(6) 0.0214(2) Uani 1 1 d . . . . .
Cl2C Cl 0.70735(7) 0.26472(6) 0.28678(6) 0.0226(2) Uani 1 1 d . . . . .
O2C O 0.63961(17) -0.04461(17) -0.03492(17) 0.0201(5) Uani 1 1 d . . . . .
H2C H 0.5790 -0.0387 -0.0317 0.030 Uiso 1 1 calc R U . . .
O3C O 0.57645(17) 0.08452(18) 0.09955(17) 0.0218(5) Uani 1 1 d . . . . .
O5C O 0.93357(18) 0.27634(17) 0.28406(16) 0.0195(5) Uani 1 1 d . . . . .
O6C O 0.99245(18) 0.15233(17) 0.14072(17) 0.0209(5) Uani 1 1 d . . . . .
C11C C 0.8192(3) 0.0444(2) 0.0511(2) 0.0169(7) Uani 1 1 d . . . . .
C12C C 0.7142(3) 0.0315(2) 0.0413(2) 0.0175(7) Uani 1 1 d . . . . .
C13C C 0.6757(2) 0.1027(2) 0.1175(2) 0.0163(7) Uani 1 1 d . . . . .
C14C C 0.7520(3) 0.1836(3) 0.2003(2) 0.0186(7) Uani 1 1 d . . . . .
C15C C 0.8618(3) 0.2040(2) 0.2135(2) 0.0159(7) Uani 1 1 d . . . . .
C16C C 0.8986(3) 0.1319(2) 0.1338(2) 0.0175(7) Uani 1 1 d . . . . .
Cl1D Cl 0.36000(6) 0.46556(6) -0.03971(6) 0.0213(2) Uani 1 1 d . . . . .
Cl2D Cl 0.20040(7) 0.77092(6) 0.27511(6) 0.0240(2) Uani 1 1 d . . . . .
O2D O 0.13605(18) 0.46363(17) -0.04628(16) 0.0206(5) Uani 1 1 d . . . . .
H2D H 0.0751 0.4667 -0.0421 0.031 Uiso 1 1 calc R U . . .
O3D O 0.07223(18) 0.59234(18) 0.08836(17) 0.0219(5) Uani 1 1 d . . . . .
O5D O 0.42873(18) 0.77521(18) 0.28075(17) 0.0220(5) Uani 1 1 d . . . . .
O6D O 0.48989(18) 0.65025(18) 0.13968(17) 0.0231(5) Uani 1 1 d . . . . .
C11D C 0.3151(3) 0.5480(3) 0.0438(2) 0.0169(7) Uani 1 1 d . . . . .
C12D C 0.2097(3) 0.5388(2) 0.0315(2) 0.0173(7) Uani 1 1 d . . . . .
C13D C 0.1709(3) 0.6103(2) 0.1054(2) 0.0164(7) Uani 1 1 d . . . . .
C14D C 0.2471(3) 0.6910(2) 0.1900(2) 0.0170(7) Uani 1 1 d . . . . .
C15D C 0.3569(3) 0.7065(3) 0.2068(2) 0.0186(7) Uani 1 1 d . . . . .
C16D C 0.3947(3) 0.6335(3) 0.1285(2) 0.0182(7) Uani 1 1 d . . . . .
N1A N 0.8449(2) 0.5524(2) 0.81388(19) 0.0170(6) Uani 1 1 d . . . . .
H1A H 0.7753 0.5255 0.7910 0.020 Uiso 1 1 calc R U . . .
N2A N 1.0597(2) 0.6346(2) 0.8825(2) 0.0205(6) Uani 1 1 d . . . . .
C2A C 0.8863(3) 0.6387(2) 0.8970(2) 0.0187(7) Uani 1 1 d . . . . .
C3A C 0.9980(3) 0.6784(2) 0.9312(2) 0.0193(8) Uani 1 1 d . . . . .
C5A C 1.0154(3) 0.5491(3) 0.7990(2) 0.0194(7) Uani 1 1 d . . . . .
C6A C 0.9058(3) 0.5058(3) 0.7647(2) 0.0196(7) Uani 1 1 d . . . . .
H6A H 0.8745 0.4439 0.7070 0.024 Uiso 1 1 calc R U . . .
C21A C 0.8134(3) 0.6874(3) 0.9471(3) 0.0221(8) Uani 1 1 d . . . . .
H21A H 0.7394 0.6466 0.9102 0.033 Uiso 1 1 calc R U . . .
H22A H 0.8208 0.7555 0.9521 0.033 Uiso 1 1 calc R U . . .
H23A H 0.8320 0.6921 1.0119 0.033 Uiso 1 1 calc R U . . .
C31A C 1.0501(3) 0.7723(3) 1.0254(2) 0.0242(8) Uani 1 1 d . . . . .
H31A H 1.1275 0.7900 1.0385 0.036 Uiso 1 1 calc R U . . .
H32A H 1.0347 0.7600 1.0773 0.036 Uiso 1 1 calc R U . . .
H33A H 1.0221 0.8281 1.0222 0.036 Uiso 1 1 calc R U . . .
C51A C 1.0875(3) 0.5045(3) 0.7458(3) 0.0236(8) Uani 1 1 d . . . . .
H51A H 1.1219 0.5527 0.7274 0.035 Uiso 1 1 calc R U . . .
H52A H 1.0458 0.4416 0.6877 0.035 Uiso 1 1 calc R U . . .
H53A H 1.1423 0.4900 0.7873 0.035 Uiso 1 1 calc R U . . .
N1B N 0.4399(2) 0.0965(2) 0.8413(2) 0.0199(6) Uani 1 1 d . . . . .
H1B H 0.3700 0.0761 0.8145 0.024 Uiso 1 1 calc R U . . .
N2B N 0.6560(2) 0.1587(2) 0.9216(2) 0.0205(6) Uani 1 1 d . . . . .
C2B C 0.4827(3) 0.1777(2) 0.9281(2) 0.0198(8) Uani 1 1 d . . . . .
C3B C 0.5949(3) 0.2077(2) 0.9679(2) 0.0189(7) Uani 1 1 d . . . . .
C5B C 0.6092(3) 0.0771(3) 0.8344(2) 0.0206(8) Uani 1 1 d . . . . .
C6B C 0.4993(3) 0.0452(3) 0.7935(3) 0.0199(8) Uani 1 1 d . . . . .
H6B H 0.4663 -0.0124 0.7323 0.024 Uiso 1 1 calc R U . . .
C21B C 0.4122(3) 0.2315(3) 0.9776(3) 0.0238(8) Uani 1 1 d . . . . .
H21B H 0.3374 0.1979 0.9371 0.036 Uiso 1 1 calc R U . . .
H22B H 0.4297 0.3020 0.9887 0.036 Uiso 1 1 calc R U . . .
H23B H 0.4233 0.2299 1.0395 0.036 Uiso 1 1 calc R U . . .
C31B C 0.6483(3) 0.2973(3) 1.0643(2) 0.0232(8) Uani 1 1 d . . . . .
H31B H 0.7260 0.3097 1.0802 0.035 Uiso 1 1 calc R U . . .
H32B H 0.6262 0.2842 1.1132 0.035 Uiso 1 1 calc R U . . .
H33B H 0.6277 0.3570 1.0629 0.035 Uiso 1 1 calc R U . . .
C51B C 0.6800(3) 0.0245(3) 0.7839(3) 0.0257(8) Uani 1 1 d . . . . .
H51B H 0.7288 0.0727 0.7751 0.038 Uiso 1 1 calc R U . . .
H52B H 0.6362 -0.0313 0.7208 0.038 Uiso 1 1 calc R U . . .
H53B H 0.7214 -0.0024 0.8227 0.038 Uiso 1 1 calc R U . . .
N1C N 1.1452(2) 0.3300(2) 0.3264(2) 0.0185(6) Uani 1 1 d . . . . .
H1C H 1.0755 0.3037 0.3033 0.022 Uiso 1 1 calc R U . . .
N2C N 1.3599(2) 0.4101(2) 0.3945(2) 0.0204(6) Uani 1 1 d . . . . .
C2C C 1.1862(3) 0.4156(2) 0.4087(2) 0.0186(7) Uani 1 1 d . . . . .
C3C C 1.2986(3) 0.4546(3) 0.4434(2) 0.0193(7) Uani 1 1 d . . . . .
C5C C 1.3159(3) 0.3245(3) 0.3112(2) 0.0198(8) Uani 1 1 d . . . . .
C6C C 1.2060(3) 0.2822(3) 0.2770(2) 0.0197(7) Uani 1 1 d . . . . .
H6C H 1.1741 0.2203 0.2194 0.024 Uiso 1 1 calc R U . . .
C21C C 1.1148(3) 0.4651(3) 0.4599(2) 0.0222(8) Uani 1 1 d . . . . .
H21C H 1.0401 0.4282 0.4210 0.033 Uiso 1 1 calc R U . . .
H22C H 1.1272 0.5353 0.4700 0.033 Uiso 1 1 calc R U . . .
H23C H 1.1301 0.4644 0.5225 0.033 Uiso 1 1 calc R U . . .
C31C C 1.3503(3) 0.5479(3) 0.5367(2) 0.0218(8) Uani 1 1 d . . . . .
H31C H 1.4277 0.5653 0.5501 0.033 Uiso 1 1 calc R U . . .
H32C H 1.3344 0.5361 0.5885 0.033 Uiso 1 1 calc R U . . .
H33C H 1.3228 0.6039 0.5331 0.033 Uiso 1 1 calc R U . . .
C51C C 1.3868(3) 0.2764(3) 0.2588(3) 0.0257(8) Uani 1 1 d . . . . .
H51C H 1.4256 0.3240 0.2424 0.039 Uiso 1 1 calc R U . . .
H52C H 1.3436 0.2151 0.1996 0.039 Uiso 1 1 calc R U . . .
H53C H 1.4379 0.2583 0.2999 0.039 Uiso 1 1 calc R U . . .
N1D N 0.6444(2) 0.8188(2) 0.3326(2) 0.0207(6) Uani 1 1 d . . . . .
H1D H 0.5745 0.7965 0.3063 0.025 Uiso 1 1 calc R U . . .
N2D N 0.8598(2) 0.8857(2) 0.4127(2) 0.0196(6) Uani 1 1 d . . . . .
C2D C 0.6853(3) 0.9008(2) 0.4182(2) 0.0186(7) Uani 1 1 d . . . . .
C3D C 0.7976(3) 0.9328(2) 0.4581(2) 0.0191(7) Uani 1 1 d . . . . .
C5D C 0.8148(3) 0.8039(2) 0.3257(2) 0.0196(7) Uani 1 1 d . . . . .
C6D C 0.7045(3) 0.7684(3) 0.2845(2) 0.0201(8) Uani 1 1 d . . . . .
H6D H 0.6723 0.7101 0.2238 0.024 Uiso 1 1 calc R U . . .
C21D C 0.6133(3) 0.9537(3) 0.4654(3) 0.0223(8) Uani 1 1 d . . . . .
H21D H 0.5388 0.9161 0.4266 0.033 Uiso 1 1 calc R U . . .
H22D H 0.6261 1.0222 0.4710 0.033 Uiso 1 1 calc R U . . .
H23D H 0.6275 0.9578 0.5298 0.033 Uiso 1 1 calc R U . . .
C31D C 0.8501(3) 1.0239(3) 0.5545(2) 0.0231(8) Uani 1 1 d . . . . .
H31D H 0.9276 1.0407 0.5684 0.035 Uiso 1 1 calc R U . . .
H32D H 0.8330 1.0091 0.6045 0.035 Uiso 1 1 calc R U . . .
H33D H 0.8238 1.0814 0.5537 0.035 Uiso 1 1 calc R U . . .
C51D C 0.8872(3) 0.7552(3) 0.2751(3) 0.0274(8) Uani 1 1 d . . . . .
H51D H 0.9252 0.8014 0.2568 0.041 Uiso 1 1 calc R U . . .
H52D H 0.8450 0.6924 0.2171 0.041 Uiso 1 1 calc R U . . .
H53D H 0.9390 0.7397 0.3182 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1A C11A 1.720(3) . ?
Cl2A C14A 1.727(3) . ?
O2A C12A 1.325(4) . ?
O2A H2A 0.8400 . ?
O3A C13A 1.250(4) . ?
O5A C15A 1.252(4) . ?
O6A C16A 1.229(4) . ?
C11A C12A 1.349(5) . ?
C11A C16A 1.456(5) . ?
C12A C13A 1.516(5) . ?
C13A C14A 1.402(5) . ?
C14A C15A 1.401(5) . ?
C15A C16A 1.537(5) . ?
Cl1B C11B 1.716(3) . ?
Cl2B C14B 1.732(3) . ?
O2B C12B 1.324(4) . ?
O2B H2B 0.8400 . ?
O3B C13B 1.250(4) . ?
O5B C15B 1.264(4) . ?
O6B C16B 1.231(4) . ?
C11B C12B 1.356(4) . ?
C11B C16B 1.438(5) . ?
C12B C13B 1.507(5) . ?
C13B C14B 1.410(5) . ?
C14B C15B 1.392(5) . ?
C15B C16B 1.545(5) . ?
Cl1C C11C 1.716(3) . ?
Cl2C C14C 1.730(4) . ?
O2C C12C 1.326(4) . ?
O2C H2C 0.8400 . ?
O3C C13C 1.255(4) . ?
O5C C15C 1.254(4) . ?
O6C C16C 1.216(4) . ?
C11C C12C 1.351(5) . ?
C11C C16C 1.461(5) . ?
C12C C13C 1.516(5) . ?
C13C C14C 1.406(5) . ?
C14C C15C 1.402(5) . ?
C15C C16C 1.541(5) . ?
Cl1D C11D 1.713(3) . ?
Cl2D C14D 1.727(3) . ?
O2D C12D 1.327(4) . ?
O2D H2D 0.8400 . ?
O3D C13D 1.248(4) . ?
O5D C15D 1.257(4) . ?
O6D C16D 1.217(4) . ?
C11D C12D 1.355(5) . ?
C11D C16D 1.461(5) . ?
C12D C13D 1.498(5) . ?
C13D C14D 1.417(5) . ?
C14D C15D 1.395(5) . ?
C15D C16D 1.541(5) . ?
N1A C6A 1.340(4) . ?
N1A C2A 1.345(4) . ?
N1A H1A 0.8800 . ?
N2A C3A 1.331(4) . ?
N2A C5A 1.343(4) . ?
C2A C3A 1.407(5) . ?
C2A C21A 1.494(5) . ?
C3A C31A 1.499(5) . ?
C5A C6A 1.388(5) . ?
C5A C51A 1.490(5) . ?
C6A H6A 0.9500 . ?
C21A H21A 0.9800 . ?
C21A H22A 0.9800 . ?
C21A H23A 0.9800 . ?
C31A H31A 0.9800 . ?
C31A H32A 0.9800 . ?
C31A H33A 0.9800 . ?
C51A H51A 0.9800 . ?
C51A H52A 0.9800 . ?
C51A H53A 0.9800 . ?
N1B C6B 1.340(4) . ?
N1B C2B 1.341(4) . ?
N1B H1B 0.8800 . ?
N2B C3B 1.332(4) . ?
N2B C5B 1.351(4) . ?
C2B C3B 1.409(5) . ?
C2B C21B 1.490(5) . ?
C3B C31B 1.492(5) . ?
C5B C6B 1.381(5) . ?
C5B C51B 1.495(5) . ?
C6B H6B 0.9500 . ?
C21B H21B 0.9800 . ?
C21B H22B 0.9800 . ?
C21B H23B 0.9800 . ?
C31B H31B 0.9800 . ?
C31B H32B 0.9800 . ?
C31B H33B 0.9800 . ?
C51B H51B 0.9800 . ?
C51B H52B 0.9800 . ?
C51B H53B 0.9800 . ?
N1C C2C 1.332(4) . ?
N1C C6C 1.348(4) . ?
N1C H1C 0.8800 . ?
N2C C3C 1.330(4) . ?
N2C C5C 1.342(4) . ?
C2C C3C 1.415(5) . ?
C2C C21C 1.490(5) . ?
C3C C31C 1.488(5) . ?
C5C C6C 1.390(5) . ?
C5C C51C 1.487(5) . ?
C6C H6C 0.9500 . ?
C21C H21C 0.9800 . ?
C21C H22C 0.9800 . ?
C21C H23C 0.9800 . ?
C31C H31C 0.9800 . ?
C31C H32C 0.9800 . ?
C31C H33C 0.9800 . ?
C51C H51C 0.9800 . ?
C51C H52C 0.9800 . ?
C51C H53C 0.9800 . ?
N1D C2D 1.333(4) . ?
N1D C6D 1.345(4) . ?
N1D H1D 0.8800 . ?
N2D C3D 1.327(4) . ?
N2D C5D 1.348(4) . ?
C2D C3D 1.411(5) . ?
C2D C21D 1.486(5) . ?
C3D C31D 1.500(5) . ?
C5D C6D 1.388(5) . ?
C5D C51D 1.491(5) . ?
C6D H6D 0.9500 . ?
C21D H21D 0.9800 . ?
C21D H22D 0.9800 . ?
C21D H23D 0.9800 . ?
C31D H31D 0.9800 . ?
C31D H32D 0.9800 . ?
C31D H33D 0.9800 . ?
C51D H51D 0.9800 . ?
C51D H52D 0.9800 . ?
C51D H53D 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12A O2A H2A 109.5 . . ?
C12A C11A C16A 120.3(3) . . ?
C12A C11A Cl1A 122.1(3) . . ?
C16A C11A Cl1A 117.6(2) . . ?
O2A C12A C11A 121.8(3) . . ?
O2A C12A C13A 116.9(3) . . ?
C11A C12A C13A 121.3(3) . . ?
O3A C13A C14A 125.4(3) . . ?
O3A C13A C12A 115.7(3) . . ?
C14A C13A C12A 118.8(3) . . ?
C15A C14A C13A 122.7(3) . . ?
C15A C14A Cl2A 118.9(3) . . ?
C13A C14A Cl2A 118.4(2) . . ?
O5A C15A C14A 125.8(3) . . ?
O5A C15A C16A 116.7(3) . . ?
C14A C15A C16A 117.5(3) . . ?
O6A C16A C11A 122.8(3) . . ?
O6A C16A C15A 118.0(3) . . ?
C11A C16A C15A 119.2(3) . . ?
C12B O2B H2B 109.5 . . ?
C12B C11B C16B 120.1(3) . . ?
C12B C11B Cl1B 121.6(3) . . ?
C16B C11B Cl1B 118.3(2) . . ?
O2B C12B C11B 121.5(3) . . ?
O2B C12B C13B 116.8(3) . . ?
C11B C12B C13B 121.7(3) . . ?
O3B C13B C14B 125.1(3) . . ?
O3B C13B C12B 116.3(3) . . ?
C14B C13B C12B 118.6(3) . . ?
C15B C14B C13B 122.6(3) . . ?
C15B C14B Cl2B 119.5(3) . . ?
C13B C14B Cl2B 117.9(3) . . ?
O5B C15B C14B 126.1(3) . . ?
O5B C15B C16B 116.5(3) . . ?
C14B C15B C16B 117.4(3) . . ?
O6B C16B C11B 123.0(3) . . ?
O6B C16B C15B 117.4(3) . . ?
C11B C16B C15B 119.6(3) . . ?
C12C O2C H2C 109.5 . . ?
C12C C11C C16C 120.2(3) . . ?
C12C C11C Cl1C 121.9(3) . . ?
C16C C11C Cl1C 117.8(2) . . ?
O2C C12C C11C 121.9(3) . . ?
O2C C12C C13C 116.5(3) . . ?
C11C C12C C13C 121.6(3) . . ?
O3C C13C C14C 125.5(3) . . ?
O3C C13C C12C 116.0(3) . . ?
C14C C13C C12C 118.6(3) . . ?
C15C C14C C13C 122.8(3) . . ?
C15C C14C Cl2C 118.9(3) . . ?
C13C C14C Cl2C 118.2(2) . . ?
O5C C15C C14C 126.1(3) . . ?
O5C C15C C16C 116.4(3) . . ?
C14C C15C C16C 117.5(3) . . ?
O6C C16C C11C 122.5(3) . . ?
O6C C16C C15C 118.5(3) . . ?
C11C C16C C15C 119.0(3) . . ?
C12D O2D H2D 109.5 . . ?
C12D C11D C16D 119.8(3) . . ?
C12D C11D Cl1D 122.4(3) . . ?
C16D C11D Cl1D 117.8(3) . . ?
O2D C12D C11D 120.8(3) . . ?
O2D C12D C13D 117.0(3) . . ?
C11D C12D C13D 122.2(3) . . ?
O3D C13D C14D 124.5(3) . . ?
O3D C13D C12D 116.7(3) . . ?
C14D C13D C12D 118.7(3) . . ?
C15D C14D C13D 122.4(3) . . ?
C15D C14D Cl2D 119.8(3) . . ?
C13D C14D Cl2D 117.8(3) . . ?
O5D C15D C14D 125.7(3) . . ?
O5D C15D C16D 116.4(3) . . ?
C14D C15D C16D 117.9(3) . . ?
O6D C16D C11D 122.8(3) . . ?
O6D C16D C15D 118.3(3) . . ?
C11D C16D C15D 118.9(3) . . ?
C6A N1A C2A 122.3(3) . . ?
C6A N1A H1A 118.9 . . ?
C2A N1A H1A 118.9 . . ?
C3A N2A C5A 119.7(3) . . ?
N1A C2A C3A 116.8(3) . . ?
N1A C2A C21A 119.4(3) . . ?
C3A C2A C21A 123.8(3) . . ?
N2A C3A C2A 121.8(3) . . ?
N2A C3A C31A 118.4(3) . . ?
C2A C3A C31A 119.7(3) . . ?
N2A C5A C6A 120.1(3) . . ?
N2A C5A C51A 117.6(3) . . ?
C6A C5A C51A 122.3(3) . . ?
N1A C6A C5A 119.2(3) . . ?
N1A C6A H6A 120.4 . . ?
C5A C6A H6A 120.4 . . ?
C2A C21A H21A 109.5 . . ?
C2A C21A H22A 109.5 . . ?
H21A C21A H22A 109.5 . . ?
C2A C21A H23A 109.5 . . ?
H21A C21A H23A 109.5 . . ?
H22A C21A H23A 109.5 . . ?
C3A C31A H31A 109.5 . . ?
C3A C31A H32A 109.5 . . ?
H31A C31A H32A 109.5 . . ?
C3A C31A H33A 109.5 . . ?
H31A C31A H33A 109.5 . . ?
H32A C31A H33A 109.5 . . ?
C5A C51A H51A 109.5 . . ?
C5A C51A H52A 109.5 . . ?
H51A C51A H52A 109.5 . . ?
C5A C51A H53A 109.5 . . ?
H51A C51A H53A 109.5 . . ?
H52A C51A H53A 109.5 . . ?
C6B N1B C2B 122.7(3) . . ?
C6B N1B H1B 118.6 . . ?
C2B N1B H1B 118.6 . . ?
C3B N2B C5B 119.3(3) . . ?
N1B C2B C3B 116.6(3) . . ?
N1B C2B C21B 120.2(3) . . ?
C3B C2B C21B 123.3(3) . . ?
N2B C3B C2B 122.0(3) . . ?
N2B C3B C31B 118.4(3) . . ?
C2B C3B C31B 119.7(3) . . ?
N2B C5B C6B 120.4(3) . . ?
N2B C5B C51B 117.9(3) . . ?
C6B C5B C51B 121.7(3) . . ?
N1B C6B C5B 119.1(3) . . ?
N1B C6B H6B 120.5 . . ?
C5B C6B H6B 120.5 . . ?
C2B C21B H21B 109.5 . . ?
C2B C21B H22B 109.5 . . ?
H21B C21B H22B 109.5 . . ?
C2B C21B H23B 109.5 . . ?
H21B C21B H23B 109.5 . . ?
H22B C21B H23B 109.5 . . ?
C3B C31B H31B 109.5 . . ?
C3B C31B H32B 109.5 . . ?
H31B C31B H32B 109.5 . . ?
C3B C31B H33B 109.5 . . ?
H31B C31B H33B 109.5 . . ?
H32B C31B H33B 109.5 . . ?
C5B C51B H51B 109.5 . . ?
C5B C51B H52B 109.5 . . ?
H51B C51B H52B 109.5 . . ?
C5B C51B H53B 109.5 . . ?
H51B C51B H53B 109.5 . . ?
H52B C51B H53B 109.5 . . ?
C2C N1C C6C 122.7(3) . . ?
C2C N1C H1C 118.6 . . ?
C6C N1C H1C 118.6 . . ?
C3C N2C C5C 120.2(3) . . ?
N1C C2C C3C 116.6(3) . . ?
N1C C2C C21C 120.2(3) . . ?
C3C C2C C21C 123.2(3) . . ?
N2C C3C C2C 121.7(3) . . ?
N2C C3C C31C 118.8(3) . . ?
C2C C3C C31C 119.5(3) . . ?
N2C C5C C6C 119.5(3) . . ?
N2C C5C C51C 118.7(3) . . ?
C6C C5C C51C 121.7(3) . . ?
N1C C6C C5C 119.2(3) . . ?
N1C C6C H6C 120.4 . . ?
C5C C6C H6C 120.4 . . ?
C2C C21C H21C 109.5 . . ?
C2C C21C H22C 109.5 . . ?
H21C C21C H22C 109.5 . . ?
C2C C21C H23C 109.5 . . ?
H21C C21C H23C 109.5 . . ?
H22C C21C H23C 109.5 . . ?
C3C C31C H31C 109.5 . . ?
C3C C31C H32C 109.5 . . ?
H31C C31C H32C 109.5 . . ?
C3C C31C H33C 109.5 . . ?
H31C C31C H33C 109.5 . . ?
H32C C31C H33C 109.5 . . ?
C5C C51C H51C 109.5 . . ?
C5C C51C H52C 109.5 . . ?
H51C C51C H52C 109.5 . . ?
C5C C51C H53C 109.5 . . ?
H51C C51C H53C 109.5 . . ?
H52C C51C H53C 109.5 . . ?
C2D N1D C6D 123.5(3) . . ?
C2D N1D H1D 118.3 . . ?
C6D N1D H1D 118.3 . . ?
C3D N2D C5D 119.3(3) . . ?
N1D C2D C3D 116.2(3) . . ?
N1D C2D C21D 120.1(3) . . ?
C3D C2D C21D 123.7(3) . . ?
N2D C3D C2D 122.3(3) . . ?
N2D C3D C31D 118.1(3) . . ?
C2D C3D C31D 119.6(3) . . ?
N2D C5D C6D 120.4(3) . . ?
N2D C5D C51D 117.9(3) . . ?
C6D C5D C51D 121.7(3) . . ?
N1D C6D C5D 118.3(3) . . ?
N1D C6D H6D 120.8 . . ?
C5D C6D H6D 120.9 . . ?
C2D C21D H21D 109.5 . . ?
C2D C21D H22D 109.5 . . ?
H21D C21D H22D 109.5 . . ?
C2D C21D H23D 109.5 . . ?
H21D C21D H23D 109.5 . . ?
H22D C21D H23D 109.5 . . ?
C3D C31D H31D 109.5 . . ?
C3D C31D H32D 109.5 . . ?
H31D C31D H32D 109.5 . . ?
C3D C31D H33D 109.5 . . ?
H31D C31D H33D 109.5 . . ?
H32D C31D H33D 109.5 . . ?
C5D C51D H51D 109.5 . . ?
C5D C51D H52D 109.5 . . ?
H51D C51D H52D 109.5 . . ?
C5D C51D H53D 109.5 . . ?
H51D C51D H53D 109.5 . . ?
H52D C51D H53D 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16A C11A C12A O2A 178.7(3) . . . . ?
Cl1A C11A C12A O2A 0.1(4) . . . . ?
C16A C11A C12A C13A -1.1(4) . . . . ?
Cl1A C11A C12A C13A -179.6(2) . . . . ?
O2A C12A C13A O3A -1.0(4) . . . . ?
C11A C12A C13A O3A 178.8(3) . . . . ?
O2A C12A C13A C14A 178.1(3) . . . . ?
C11A C12A C13A C14A -2.1(4) . . . . ?
O3A C13A C14A C15A -178.6(3) . . . . ?
C12A C13A C14A C15A 2.4(4) . . . . ?
O3A C13A C14A Cl2A 1.2(4) . . . . ?
C12A C13A C14A Cl2A -177.7(2) . . . . ?
C13A C14A C15A O5A 180.0(3) . . . . ?
Cl2A C14A C15A O5A 0.2(4) . . . . ?
C13A C14A C15A C16A 0.3(4) . . . . ?
Cl2A C14A C15A C16A -179.5(2) . . . . ?
C12A C11A C16A O6A -174.4(3) . . . . ?
Cl1A C11A C16A O6A 4.2(4) . . . . ?
C12A C11A C16A C15A 3.8(4) . . . . ?
Cl1A C11A C16A C15A -177.6(2) . . . . ?
O5A C15A C16A O6A -4.8(4) . . . . ?
C14A C15A C16A O6A 174.9(3) . . . . ?
O5A C15A C16A C11A 176.8(3) . . . . ?
C14A C15A C16A C11A -3.5(4) . . . . ?
C16B C11B C12B O2B 178.7(3) . . . . ?
Cl1B C11B C12B O2B 0.8(4) . . . . ?
C16B C11B C12B C13B -2.2(4) . . . . ?
Cl1B C11B C12B C13B 179.9(2) . . . . ?
O2B C12B C13B O3B 1.1(4) . . . . ?
C11B C12B C13B O3B -178.0(3) . . . . ?
O2B C12B C13B C14B -179.5(3) . . . . ?
C11B C12B C13B C14B 1.4(4) . . . . ?
O3B C13B C14B C15B 177.9(3) . . . . ?
C12B C13B C14B C15B -1.4(4) . . . . ?
O3B C13B C14B Cl2B -1.3(4) . . . . ?
C12B C13B C14B Cl2B 179.4(2) . . . . ?
C13B C14B C15B O5B -178.4(3) . . . . ?
Cl2B C14B C15B O5B 0.9(4) . . . . ?
C13B C14B C15B C16B 2.2(4) . . . . ?
Cl2B C14B C15B C16B -178.6(2) . . . . ?
C12B C11B C16B O6B -175.2(3) . . . . ?
Cl1B C11B C16B O6B 2.8(4) . . . . ?
C12B C11B C16B C15B 3.0(4) . . . . ?
Cl1B C11B C16B C15B -179.1(2) . . . . ?
O5B C15B C16B O6B -4.2(4) . . . . ?
C14B C15B C16B O6B 175.3(3) . . . . ?
O5B C15B C16B C11B 177.5(3) . . . . ?
C14B C15B C16B C11B -2.9(4) . . . . ?
C16C C11C C12C O2C 177.0(3) . . . . ?
Cl1C C11C C12C O2C 0.1(4) . . . . ?
C16C C11C C12C C13C -3.6(5) . . . . ?
Cl1C C11C C12C C13C 179.5(2) . . . . ?
O2C C12C C13C O3C -2.1(4) . . . . ?
C11C C12C C13C O3C 178.5(3) . . . . ?
O2C C12C C13C C14C 179.0(3) . . . . ?
C11C C12C C13C C14C -0.4(4) . . . . ?
O3C C13C C14C C15C -175.7(3) . . . . ?
C12C C13C C14C C15C 3.1(4) . . . . ?
O3C C13C C14C Cl2C 1.2(4) . . . . ?
C12C C13C C14C Cl2C 179.9(2) . . . . ?
C13C C14C C15C O5C 177.9(3) . . . . ?
Cl2C C14C C15C O5C 1.0(4) . . . . ?
C13C C14C C15C C16C -1.6(4) . . . . ?
Cl2C C14C C15C C16C -178.5(2) . . . . ?
C12C C11C C16C O6C -172.3(3) . . . . ?
Cl1C C11C C16C O6C 4.7(4) . . . . ?
C12C C11C C16C C15C 4.9(4) . . . . ?
Cl1C C11C C16C C15C -178.1(2) . . . . ?
O5C C15C C16C O6C -4.6(4) . . . . ?
C14C C15C C16C O6C 175.0(3) . . . . ?
O5C C15C C16C C11C 178.1(3) . . . . ?
C14C C15C C16C C11C -2.3(4) . . . . ?
C16D C11D C12D O2D 177.9(3) . . . . ?
Cl1D C11D C12D O2D 0.9(4) . . . . ?
C16D C11D C12D C13D -3.9(5) . . . . ?
Cl1D C11D C12D C13D 179.1(2) . . . . ?
O2D C12D C13D O3D 1.0(4) . . . . ?
C11D C12D C13D O3D -177.2(3) . . . . ?
O2D C12D C13D C14D 179.4(3) . . . . ?
C11D C12D C13D C14D 1.2(4) . . . . ?
O3D C13D C14D C15D 178.4(3) . . . . ?
C12D C13D C14D C15D 0.1(4) . . . . ?
O3D C13D C14D Cl2D -0.5(4) . . . . ?
C12D C13D C14D Cl2D -178.8(2) . . . . ?
C13D C14D C15D O5D -178.6(3) . . . . ?
Cl2D C14D C15D O5D 0.3(5) . . . . ?
C13D C14D C15D C16D 1.4(4) . . . . ?
Cl2D C14D C15D C16D -179.8(2) . . . . ?
C12D C11D C16D O6D -174.0(3) . . . . ?
Cl1D C11D C16D O6D 3.1(4) . . . . ?
C12D C11D C16D C15D 5.3(4) . . . . ?
Cl1D C11D C16D C15D -177.6(2) . . . . ?
O5D C15D C16D O6D -4.7(4) . . . . ?
C14D C15D C16D O6D 175.3(3) . . . . ?
O5D C15D C16D C11D 175.9(3) . . . . ?
C14D C15D C16D C11D -4.0(4) . . . . ?
C6A N1A C2A C3A -0.5(4) . . . . ?
C6A N1A C2A C21A 178.9(3) . . . . ?
C5A N2A C3A C2A -1.1(4) . . . . ?
C5A N2A C3A C31A 178.5(3) . . . . ?
N1A C2A C3A N2A 1.9(4) . . . . ?
C21A C2A C3A N2A -177.5(3) . . . . ?
N1A C2A C3A C31A -177.6(3) . . . . ?
C21A C2A C3A C31A 3.0(5) . . . . ?
C3A N2A C5A C6A -1.2(4) . . . . ?
C3A N2A C5A C51A 178.3(3) . . . . ?
C2A N1A C6A C5A -1.7(4) . . . . ?
N2A C5A C6A N1A 2.6(4) . . . . ?
C51A C5A C6A N1A -176.9(3) . . . . ?
C6B N1B C2B C3B 0.2(4) . . . . ?
C6B N1B C2B C21B -179.9(3) . . . . ?
C5B N2B C3B C2B -0.7(5) . . . . ?
C5B N2B C3B C31B 179.7(3) . . . . ?
N1B C2B C3B N2B 0.5(5) . . . . ?
C21B C2B C3B N2B -179.4(3) . . . . ?
N1B C2B C3B C31B -180.0(3) . . . . ?
C21B C2B C3B C31B 0.1(5) . . . . ?
C3B N2B C5B C6B 0.3(5) . . . . ?
C3B N2B C5B C51B 179.3(3) . . . . ?
C2B N1B C6B C5B -0.6(5) . . . . ?
N2B C5B C6B N1B 0.3(5) . . . . ?
C51B C5B C6B N1B -178.6(3) . . . . ?
C6C N1C C2C C3C -0.5(4) . . . . ?
C6C N1C C2C C21C 179.8(3) . . . . ?
C5C N2C C3C C2C -1.6(4) . . . . ?
C5C N2C C3C C31C 178.4(3) . . . . ?
N1C C2C C3C N2C 2.2(4) . . . . ?
C21C C2C C3C N2C -178.1(3) . . . . ?
N1C C2C C3C C31C -177.8(3) . . . . ?
C21C C2C C3C C31C 1.9(5) . . . . ?
C3C N2C C5C C6C -0.7(4) . . . . ?
C3C N2C C5C C51C -179.7(3) . . . . ?
C2C N1C C6C C5C -1.7(4) . . . . ?
N2C C5C C6C N1C 2.4(4) . . . . ?
C51C C5C C6C N1C -178.7(3) . . . . ?
C6D N1D C2D C3D -0.9(4) . . . . ?
C6D N1D C2D C21D 178.3(3) . . . . ?
C5D N2D C3D C2D -0.5(4) . . . . ?
C5D N2D C3D C31D -179.7(3) . . . . ?
N1D C2D C3D N2D 1.3(4) . . . . ?
C21D C2D C3D N2D -177.8(3) . . . . ?
N1D C2D C3D C31D -179.5(3) . . . . ?
C21D C2D C3D C31D 1.3(5) . . . . ?
C3D N2D C5D C6D -0.8(4) . . . . ?
C3D N2D C5D C51D 177.7(3) . . . . ?
C2D N1D C6D C5D -0.4(5) . . . . ?
N2D C5D C6D N1D 1.3(4) . . . . ?
C51D C5D C6D N1D -177.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A O5A 0.88 1.84 2.702(4) 165.4 .
O2A H2A O3B 0.84 1.92 2.668(3) 147.8 2_556
C6A H6A O6A 0.95 2.32 2.965(4) 124.6 .
C21A H21A O5A 0.98 2.37 3.215(5) 143.7 .
C21A H23A O2D 0.98 2.67 3.312(4) 122.9 2_666
C31A H32A O3D 0.98 2.70 3.268(4) 117.4 1_656
N1B H1B O5B 0.88 1.80 2.658(4) 165.1 .
O2B H2B O3A 0.84 1.92 2.668(3) 148.4 2_556
C6B H6B O6B 0.95 2.29 2.945(4) 125.1 .
C21B H21B O5B 0.98 2.36 3.191(5) 142.1 .
C21B H22B Cl1D 0.98 2.91 3.779(3) 148.7 1_556
C31B H32B Cl2C 0.98 2.89 3.714(4) 142.6 1_556
C51B H53B Cl1C 0.98 2.88 3.843(4) 167.8 1_556
C51B H51B Cl2D 0.98 2.88 3.812(4) 159.0 2_666
N1C H1C O5C 0.88 1.81 2.668(4) 165.3 .
O2C H2C O3C 0.84 1.97 2.715(3) 146.8 2_655
C6C H6C O6C 0.95 2.31 2.955(5) 124.6 .
C21C H21C O5C 0.98 2.36 3.190(5) 141.8 .
C31C H32C Cl2A 0.98 2.92 3.796(3) 150.0 1_655
N1D H1D O5D 0.88 1.85 2.708(4) 165.4 .
O2D H2D O3D 0.84 1.87 2.628(3) 149.4 2_565
C6D H6D O6D 0.95 2.33 2.972(5) 124.7 .
C21D H21D O5D 0.98 2.36 3.202(5) 143.5 .
C21D H23D O2A 0.98 2.72 3.349(4) 122.6 2_666
C21D H22D O6B 0.98 2.70 3.305(4) 120.7 2_666
C31D H33D Cl1B 0.98 2.91 3.800(3) 151.3 2_666

_refine_diff_density_max         0.604
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.097

