# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14kaw13
_database_code_depnum_ccdc_archive 'CCDC 1470675'
_audit_update_record             
;
2016-03-25 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
# (-)-1

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          445-447
_chemical_formula_moiety         'C4 H5 Cl O4'
_chemical_formula_sum            'C4 H5 Cl O4'
_chemical_formula_weight         152.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.5593(3)
_cell_length_b                   8.5020(3)
_cell_length_c                   9.0604(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     582.30(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5909
_cell_measurement_theta_min      7.14
_cell_measurement_theta_max      68.22

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_max          0.26
_exptl_absorpt_coefficient_mu    5.371
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.487
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8317
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         7.143
_diffrn_reflns_theta_max         68.216
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1068
_reflns_number_gt                1060
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to oxygen were
 located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with O-H bond distances restrained to 0.85(2) angstroms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+0.5716P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.08(4)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1068
_refine_ls_number_parameters     89
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.10003(14) 0.71706(13) 0.05422(12) 0.0329(3) Uani 1 1 d . . . . .
O1 O -0.2274(4) 0.4739(4) 0.1333(4) 0.0282(7) Uani 1 1 d D . . . .
H1 H -0.338(3) 0.479(7) 0.143(6) 0.034 Uiso 1 1 d D U . . .
O2 O -0.1942(4) 0.6517(4) 0.3124(4) 0.0303(8) Uani 1 1 d . . . . .
O3 O 0.4634(4) 0.6601(4) 0.3811(4) 0.0295(7) Uani 1 1 d D . . . .
H3 H 0.571(4) 0.652(7) 0.356(6) 0.035 Uiso 1 1 d D U . . .
O4 O 0.4291(3) 0.5066(4) 0.1820(3) 0.0257(7) Uani 1 1 d . . . . .
C1 C -0.1362(5) 0.5650(5) 0.2189(5) 0.0214(8) Uani 1 1 d . . . . .
C2 C 0.0619(5) 0.5575(5) 0.1855(5) 0.0260(9) Uani 1 1 d . . . . .
H2 H 0.0926 0.4540 0.1397 0.031 Uiso 1 1 calc R U . . .
C3 C 0.1731(5) 0.5854(5) 0.3192(5) 0.0262(9) Uani 1 1 d . . . . .
H3A H 0.1461 0.5040 0.3940 0.031 Uiso 1 1 calc R U . . .
H3B H 0.1426 0.6891 0.3620 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3692(5) 0.5815(5) 0.2849(5) 0.0231(9) 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
Cl1 C2 1.827(5) . ?
O1 C1 1.295(5) . ?
O1 H1 0.84(3) . ?
O2 C1 1.205(5) . ?
O3 C4 1.309(5) . ?
O3 H3 0.85(3) . ?
O4 C4 1.216(5) . ?
C1 C2 1.529(5) . ?
C2 C3 1.494(6) . ?
C2 H2 1.0000 . ?
C3 C4 1.515(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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
C1 O1 H1 116(4) . . ?
C4 O3 H3 107(4) . . ?
O2 C1 O1 126.4(4) . . ?
O2 C1 C2 121.4(4) . . ?
O1 C1 C2 112.2(4) . . ?
C3 C2 C1 112.6(4) . . ?
C3 C2 Cl1 108.7(3) . . ?
C1 C2 Cl1 104.6(3) . . ?
C3 C2 H2 110.2 . . ?
C1 C2 H2 110.2 . . ?
Cl1 C2 H2 110.2 . . ?
C2 C3 C4 112.4(4) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
O4 C4 O3 125.1(4) . . ?
O4 C4 C3 122.2(4) . . ?
O3 C4 C3 112.6(4) . . ?

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
O2 C1 C2 C3 32.8(6) . . . . ?
O1 C1 C2 C3 -149.4(4) . . . . ?
O2 C1 C2 Cl1 -85.1(5) . . . . ?
O1 C1 C2 Cl1 92.7(4) . . . . ?
C1 C2 C3 C4 -178.7(4) . . . . ?
Cl1 C2 C3 C4 -63.2(4) . . . . ?
C2 C3 C4 O4 -26.9(6) . . . . ?
C2 C3 C4 O3 156.3(4) . . . . ?

_refine_diff_density_max         0.613
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.085

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method acetone
####################################################################### 
# 
# 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_14kaw14
_database_code_depnum_ccdc_archive 'CCDC 1470676'
_audit_update_record             
;
2016-03-25 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
# rem (+)-2

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          434-436
_chemical_formula_moiety         'C4 H5 Br O4'
_chemical_formula_sum            'C4 H5 Br O4'
_chemical_formula_weight         196.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.5647(5)
_cell_length_b                   8.6337(7)
_cell_length_c                   9.2380(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     603.35(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1803
_cell_measurement_theta_min      7.02
_cell_measurement_theta_max      67.87

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.169
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.033
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_max          0.094
_exptl_absorpt_coefficient_mu    8.870
_shelx_estimated_absorpt_T_min   0.208
_shelx_estimated_absorpt_T_max   0.465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4637
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         7.020
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             1060
_reflns_number_gt                1010
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.628
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    0.937

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to oxygen were
 located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with O-H bond distances restrained to 0.85(2) angstroms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0284P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1060
_refine_ls_number_parameters     88
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0568
_refine_ls_wR_factor_gt          0.0562
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.062
_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 0.90282(7) 0.27799(7) 0.94891(7) 0.02472(19) Uani 1 1 d . . . . .
O1 O 1.2290(5) 0.5249(5) 0.8573(5) 0.0227(10) Uani 1 1 d D . . . .
H1 H 1.336(4) 0.511(8) 0.836(7) 0.027 Uiso 1 1 d D U . . .
O2 O 1.1955(5) 0.3535(5) 0.6765(4) 0.0241(10) Uani 1 1 d . . . . .
O3 O 0.5367(5) 0.3403(5) 0.6113(5) 0.0264(11) Uani 1 1 d D . . . .
H3 H 0.426(4) 0.351(7) 0.626(7) 0.032 Uiso 1 1 d D U . . .
O4 O 0.5712(5) 0.4908(5) 0.8071(4) 0.0219(10) Uani 1 1 d . . . . .
C1 C 1.1357(7) 0.4363(7) 0.7710(6) 0.0193(13) Uani 1 1 d . . . . .
C2 C 0.9397(7) 0.4443(7) 0.8029(6) 0.0204(13) Uani 1 1 d . . . . .
H2 H 0.9083 0.5476 0.8447 0.024 Uiso 1 1 calc R U . . .
C3 C 0.8265(7) 0.4101(7) 0.6726(6) 0.0219(14) Uani 1 1 d . . . . .
H3A H 0.8540 0.4858 0.5954 0.026 Uiso 1 1 calc R U . . .
H3B H 0.8558 0.3056 0.6357 0.026 Uiso 1 1 calc R U . . .
C4 C 0.6324(7) 0.4172(7) 0.7061(6) 0.0208(14) 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
Br1 C2 1.990(6) . ?
O1 C1 1.311(7) . ?
O1 H1 0.84(3) . ?
O2 C1 1.215(7) . ?
O3 C4 1.316(7) . ?
O3 H3 0.85(3) . ?
O4 C4 1.220(7) . ?
C1 C2 1.513(7) . ?
C2 C3 1.506(8) . ?
C2 H2 1.0000 . ?
C3 C4 1.502(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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
C1 O1 H1 107(5) . . ?
C4 O3 H3 112(4) . . ?
O2 C1 O1 125.4(5) . . ?
O2 C1 C2 122.1(5) . . ?
O1 C1 C2 112.5(5) . . ?
C3 C2 C1 113.1(5) . . ?
C3 C2 Br1 108.7(4) . . ?
C1 C2 Br1 103.7(4) . . ?
C3 C2 H2 110.4 . . ?
C1 C2 H2 110.4 . . ?
Br1 C2 H2 110.4 . . ?
C4 C3 C2 112.5(5) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
O4 C4 O3 124.3(5) . . ?
O4 C4 C3 123.3(5) . . ?
O3 C4 C3 112.3(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
O2 C1 C2 C3 -28.3(9) . . . . ?
O1 C1 C2 C3 152.8(5) . . . . ?
O2 C1 C2 Br1 89.2(6) . . . . ?
O1 C1 C2 Br1 -89.6(5) . . . . ?
C1 C2 C3 C4 179.5(5) . . . . ?
Br1 C2 C3 C4 65.0(6) . . . . ?
C2 C3 C4 O4 23.4(9) . . . . ?
C2 C3 C4 O3 -159.0(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
O1 H1 O4 0.84(3) 1.80(3) 2.647(5) 175(7) 1_655
O3 H3 O2 0.85(3) 1.81(3) 2.653(5) 172(6) 1_455

_refine_diff_density_max         0.607
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.082

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method acetone
####################################################################### 
# 
# 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_14kaw22
_database_code_depnum_ccdc_archive 'CCDC 1470677'
_audit_update_record             
;
2016-03-25 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
#  (rac)-2 Im

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          403-406
_chemical_formula_moiety         'C4 H4 Br O4, C3 H5 N2'
_chemical_formula_sum            'C7 H9 Br N2 O4'
_chemical_formula_weight         265.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   8.0994(4)
_cell_length_b                   8.3605(4)
_cell_length_c                   8.8967(7)
_cell_angle_alpha                101.264(3)
_cell_angle_beta                 106.468(3)
_cell_angle_gamma                118.411(2)
_cell_volume                     467.59(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8020
_cell_measurement_theta_min      5.64
_cell_measurement_theta_max      68.46

_exptl_crystal_description       'transparent prism'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    5.987
_shelx_estimated_absorpt_T_min   0.363
_shelx_estimated_absorpt_T_max   0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10122
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.635
_diffrn_reflns_theta_max         68.230
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             1670
_reflns_number_gt                1605
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to oxygen and nitrogen
 were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with O-H and N-H bond distances restrained to 0.85(2) angstroms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0877P)²+0.4364P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1670
_refine_ls_number_parameters     136
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.102
_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 0.19737(5) 0.79891(5) 0.84041(4) 0.0232(2) Uani 1 1 d . . . . .
O1 O -0.1861(4) 0.6572(4) 0.4194(3) 0.0227(5) Uani 1 1 d . . . . .
O2 O -0.1093(4) 0.9058(4) 0.6376(3) 0.0232(6) Uani 1 1 d . . . . .
O3 O 0.5004(4) 0.7467(4) 0.5235(3) 0.0250(6) Uani 1 1 d D . . . .
H22 H 0.629(4) 0.793(7) 0.557(6) 0.030 Uiso 1 1 d D U . . .
O4 O 0.5881(4) 1.0170(4) 0.7244(3) 0.0221(5) Uani 1 1 d . . . . .
N1 N -0.5860(5) 0.4560(5) 0.1779(4) 0.0228(7) Uani 1 1 d D . . . .
H20 H -0.474(5) 0.520(6) 0.267(4) 0.027 Uiso 1 1 d D U . . .
N2 N -0.8417(4) 0.2300(4) -0.0622(4) 0.0196(6) Uani 1 1 d D . . . .
H21 H -0.917(6) 0.124(4) -0.151(4) 0.023 Uiso 1 1 d D U . . .
C1 C -0.0647(5) 0.8021(5) 0.5559(4) 0.0185(7) Uani 1 1 d . . . . .
C2 C 0.1628(5) 0.8682(5) 0.6379(4) 0.0188(7) Uani 1 1 d . . . . .
H2 H 0.2557 1.0149 0.6766 0.023 Uiso 1 1 calc R U . . .
C3 C 0.2258(5) 0.7739(5) 0.5244(4) 0.0205(7) Uani 1 1 d . . . . .
H3A H 0.1876 0.7913 0.4157 0.025 Uiso 1 1 calc R U . . .
H3B H 0.1466 0.6303 0.4981 0.025 Uiso 1 1 calc R U . . .
C4 C 0.4568(5) 0.8591(5) 0.6028(4) 0.0190(7) Uani 1 1 d . . . . .
C5 C -0.6821(6) 0.2713(6) 0.0723(5) 0.0259(8) Uani 1 1 d . . . . .
H5 H -0.6435 0.1831 0.0898 0.031 Uiso 1 1 calc R U . . .
C6 C -0.6867(5) 0.5367(5) 0.1089(5) 0.0217(7) Uani 1 1 d . . . . .
H6 H -0.6508 0.6670 0.1577 0.026 Uiso 1 1 calc R U . . .
C7 C -0.8472(6) 0.3928(6) -0.0424(5) 0.0246(8) Uani 1 1 d . . . . .
H7 H -0.9455 0.4035 -0.1204 0.030 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
Br1 C2 1.984(4) . ?
O1 C1 1.234(4) . ?
O2 C1 1.270(4) . ?
O3 C4 1.305(5) . ?
O3 H22 0.85(2) . ?
O4 C4 1.224(5) . ?
N1 C5 1.322(5) . ?
N1 C6 1.378(5) . ?
N1 H20 0.84(2) . ?
N2 C5 1.326(5) . ?
N2 C7 1.361(5) . ?
N2 H21 0.847(19) . ?
C1 C2 1.531(4) . ?
C2 C3 1.505(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.514(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5 0.9500 . ?
C6 C7 1.355(5) . ?
C6 H6 0.9500 . ?
C7 H7 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
C4 O3 H22 116(3) . . ?
C5 N1 C6 109.0(3) . . ?
C5 N1 H20 126(3) . . ?
C6 N1 H20 124(3) . . ?
C5 N2 C7 108.9(3) . . ?
C5 N2 H21 125(3) . . ?
C7 N2 H21 126(3) . . ?
O1 C1 O2 126.2(3) . . ?
O1 C1 C2 118.6(3) . . ?
O2 C1 C2 115.2(3) . . ?
C3 C2 C1 114.8(3) . . ?
C3 C2 Br1 109.4(2) . . ?
C1 C2 Br1 105.9(2) . . ?
C3 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
Br1 C2 H2 108.8 . . ?
C2 C3 C4 113.3(3) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O4 C4 O3 123.8(3) . . ?
O4 C4 C3 124.0(3) . . ?
O3 C4 C3 112.2(3) . . ?
N1 C5 N2 108.4(3) . . ?
N1 C5 H5 125.8 . . ?
N2 C5 H5 125.8 . . ?
C7 C6 N1 106.2(3) . . ?
C7 C6 H6 126.9 . . ?
N1 C6 H6 126.9 . . ?
C6 C7 N2 107.5(3) . . ?
C6 C7 H7 126.3 . . ?
N2 C7 H7 126.3 . . ?

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
O1 C1 C2 C3 12.2(5) . . . . ?
O2 C1 C2 C3 -167.5(3) . . . . ?
O1 C1 C2 Br1 -108.7(3) . . . . ?
O2 C1 C2 Br1 71.7(3) . . . . ?
C1 C2 C3 C4 173.7(3) . . . . ?
Br1 C2 C3 C4 -67.4(3) . . . . ?
C2 C3 C4 O4 -16.9(5) . . . . ?
C2 C3 C4 O3 164.4(3) . . . . ?
C6 N1 C5 N2 -0.1(5) . . . . ?
C7 N2 C5 N1 0.2(5) . . . . ?
C5 N1 C6 C7 0.0(5) . . . . ?
N1 C6 C7 N2 0.2(4) . . . . ?
C5 N2 C7 C6 -0.3(4) . . . . ?

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 H20 O1 0.84(2) 1.91(2) 2.719(4) 162(5) .
O3 H22 O2 0.85(2) 1.69(2) 2.538(3) 174(5) 1_655
N2 H21 O2 0.847(19) 1.90(2) 2.734(4) 171(5) 1_444

_refine_diff_density_max         1.786
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.166

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method '5:1 methanol:water/acetone'
####################################################################### 
# 
# 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_15kaw20
_database_code_depnum_ccdc_archive 'CCDC 1470678'
_audit_update_record             
;
2016-03-25 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

# (-)-2 Im

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          394-396
_chemical_formula_moiety         'C4 H4 Br O4, C3 H5 N2'
_chemical_formula_sum            'C7 H9 Br N2 O4'
_chemical_formula_weight         265.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.2825(2)
_cell_length_b                   8.8079(3)
_cell_length_c                   8.0544(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.936(2)
_cell_angle_gamma                90
_cell_volume                     488.68(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7654
_cell_measurement_theta_min      5.81
_cell_measurement_theta_max      68.32

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.028
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_max          0.133
_exptl_absorpt_coefficient_mu    5.729
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.609
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10932
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.807
_diffrn_reflns_theta_max         68.168
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1761
_reflns_number_gt                1740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_max     0.971
_reflns_Friedel_fraction_full    0.971

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to oxygen and nitrogen
 were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with O-H and N-H bond distances restrained to 0.85(2) angstroms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0238P)²+0.3077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 783 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(9)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1761
_refine_ls_number_parameters     136
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0184
_refine_ls_wR_factor_ref         0.0473
_refine_ls_wR_factor_gt          0.0473
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.078
_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 0.89121(5) 0.80146(3) 0.48256(4) 0.02189(12) Uani 1 1 d . . . . .
O1 O 0.7834(4) 1.1415(3) 0.2235(3) 0.0180(5) Uani 1 1 d . . . . .
O2 O 0.6760(4) 0.9259(3) 0.0799(3) 0.0157(6) Uani 1 1 d . . . . .
O3 O 0.7263(5) 1.0687(3) 0.8168(3) 0.0212(6) Uani 1 1 d D . . . .
H21 H 0.716(8) 1.715(4) 0.047(7) 0.025 Uiso 1 1 d D U . . .
O4 O 0.5281(5) 0.8916(3) 0.6573(4) 0.0277(7) Uani 1 1 d . . . . .
N1 N 0.7984(5) 1.3873(4) 0.0344(4) 0.0163(7) Uani 1 1 d D . . . .
H20 H 0.803(6) 1.298(3) 0.069(5) 0.020 Uiso 1 1 d D U . . .
N2 N 0.7491(5) 1.6284(4) 0.0224(4) 0.0176(6) Uani 1 1 d D . . . .
H22 H 0.705(7) 1.020(5) 0.896(5) 0.021 Uiso 1 1 d D U . . .
C1 C 0.7172(5) 1.0116(4) 0.2139(4) 0.0125(7) Uani 1 1 d . . . . .
C2 C 0.6787(5) 0.9470(4) 0.3763(4) 0.0123(7) Uani 1 1 d . . . . .
H2 H 0.5517 0.8920 0.3393 0.015 Uiso 1 1 calc R U . . .
C3 C 0.6793(5) 1.0650(4) 0.5127(4) 0.0147(7) Uani 1 1 d . . . . .
H3A H 0.5814 1.1438 0.4581 0.018 Uiso 1 1 calc R U . . .
H3B H 0.8081 1.1147 0.5540 0.018 Uiso 1 1 calc R U . . .
C4 C 0.6353(5) 0.9977(4) 0.6683(5) 0.0134(7) Uani 1 1 d . . . . .
C5 C 0.7520(5) 1.5043(5) 0.1159(5) 0.0177(8) Uani 1 1 d . . . . .
H5 H 0.7251 1.5000 0.2236 0.021 Uiso 1 1 calc R U . . .
C6 C 0.8288(6) 1.4374(4) -0.1156(5) 0.0180(8) Uani 1 1 d . . . . .
H6 H 0.8654 1.3774 -0.1978 0.022 Uiso 1 1 calc R U . . .
C7 C 0.7963(6) 1.5895(5) -0.1241(5) 0.0185(8) Uani 1 1 d . . . . .
H7 H 0.8047 1.6562 -0.2140 0.022 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.978(3) . ?
O1 C1 1.233(5) . ?
O2 C1 1.271(4) . ?
O3 C4 1.322(5) . ?
O3 H22 0.82(3) . ?
O4 C4 1.202(5) . ?
N1 C5 1.324(5) . ?
N1 C6 1.370(5) . ?
N1 H20 0.83(3) . ?
N2 C5 1.324(5) . ?
N2 C7 1.375(6) . ?
N2 H21 0.84(3) . ?
C1 C2 1.533(5) . ?
C2 C3 1.512(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.512(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5 0.9500 . ?
C6 C7 1.358(6) . ?
C6 H6 0.9500 . ?
C7 H7 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
C4 O3 H22 107(3) . . ?
C5 N1 C6 109.1(3) . . ?
C5 N1 H20 124(3) . . ?
C6 N1 H20 127(3) . . ?
C5 N2 C7 108.7(3) . . ?
C5 N2 H21 125(4) . . ?
C7 N2 H21 127(4) . . ?
O1 C1 O2 125.7(3) . . ?
O1 C1 C2 117.8(3) . . ?
O2 C1 C2 116.4(3) . . ?
C3 C2 C1 114.0(3) . . ?
C3 C2 Br1 108.3(2) . . ?
C1 C2 Br1 106.0(2) . . ?
C3 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
Br1 C2 H2 109.5 . . ?
C2 C3 C4 112.4(3) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
O4 C4 O3 123.8(3) . . ?
O4 C4 C3 123.5(3) . . ?
O3 C4 C3 112.7(3) . . ?
N2 C5 N1 108.7(3) . . ?
N2 C5 H5 125.7 . . ?
N1 C5 H5 125.7 . . ?
C7 C6 N1 106.6(3) . . ?
C7 C6 H6 126.7 . . ?
N1 C6 H6 126.7 . . ?
C6 C7 N2 106.9(3) . . ?
C6 C7 H7 126.5 . . ?
N2 C7 H7 126.5 . . ?

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
O1 C1 C2 C3 14.7(5) . . . . ?
O2 C1 C2 C3 -164.7(3) . . . . ?
O1 C1 C2 Br1 -104.3(3) . . . . ?
O2 C1 C2 Br1 76.2(3) . . . . ?
C1 C2 C3 C4 178.4(3) . . . . ?
Br1 C2 C3 C4 -63.9(3) . . . . ?
C2 C3 C4 O4 -33.0(5) . . . . ?
C2 C3 C4 O3 147.4(3) . . . . ?
C7 N2 C5 N1 -0.3(4) . . . . ?
C6 N1 C5 N2 0.7(4) . . . . ?
C5 N1 C6 C7 -0.9(4) . . . . ?
N1 C6 C7 N2 0.7(4) . . . . ?
C5 N2 C7 C6 -0.3(4) . . . . ?

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 H20 O1 0.83(3) 1.89(3) 2.670(4) 155(4) .
O3 H22 O2 0.82(3) 1.77(3) 2.591(4) 175(5) 1_556
N2 H21 O2 0.84(3) 1.91(3) 2.743(4) 169(5) 1_565

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.061

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 1-propanol
####################################################################### 
# 
# 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_14kaw24
_database_code_depnum_ccdc_archive 'CCDC 1470679'
_audit_update_record             
;
2016-03-25 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
# (+)-1 Im

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          398-401
_chemical_formula_moiety         'C4 H4 Cl O4, C3 H5 N2'
_chemical_formula_sum            'C7 H9 Cl N2 O4'
_chemical_formula_weight         220.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   5.0265(3)
_cell_length_b                   6.1840(3)
_cell_length_c                   8.1859(4)
_cell_angle_alpha                93.095(3)
_cell_angle_beta                 102.264(3)
_cell_angle_gamma                106.883(3)
_cell_volume                     236.10(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3739
_cell_measurement_theta_min      5.57
_cell_measurement_theta_max      68.04

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             114
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    3.574
_shelx_estimated_absorpt_T_min   0.466
_shelx_estimated_absorpt_T_max   0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.609
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5075
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.573
_diffrn_reflns_theta_max         68.036
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             1486
_reflns_number_gt                1465
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.974

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to oxygen and nitrogen
 were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with O-H and N-H bond distances restrained to 0.85(2) angstroms.

 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.052(19)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1486
_refine_ls_number_parameters     134
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0577
_refine_ls_wR_factor_gt          0.0575
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.25252(11) 0.66227(8) 0.03813(8) 0.02522(18) Uani 1 1 d . . . . .
O1 O 0.3477(4) 0.1656(3) -0.1559(2) 0.0245(4) Uani 1 1 d . . . . .
O2 O 0.0858(4) 0.3580(3) -0.3008(2) 0.0206(4) Uani 1 1 d . . . . .
O3 O 0.2414(4) 0.2433(3) 0.4333(2) 0.0205(4) Uani 1 1 d D . . . .
H22 H 0.185(7) 0.282(6) 0.515(4) 0.025 Uiso 1 1 d D U . . .
O4 O -0.0952(4) 0.3775(4) 0.2911(2) 0.0252(4) Uani 1 1 d . . . . .
N1 N 0.5542(5) -0.0986(4) -0.3428(3) 0.0220(5) Uani 1 1 d D . . . .
H20 H 0.471(7) -0.020(6) -0.301(4) 0.026 Uiso 1 1 d D U . . .
N2 N 0.7885(5) -0.3341(4) -0.3674(3) 0.0204(5) Uani 1 1 d D . . . .
H21 H 0.8816 -0.4332 -0.3429 0.025 Uiso 1 1 calc DR U . . .
C1 C 0.1878(5) 0.2853(4) -0.1683(3) 0.0166(5) Uani 1 1 d . . . . .
C2 C 0.1007(5) 0.3541(4) -0.0081(3) 0.0167(5) Uani 1 1 d . . . . .
H2 H -0.1127 0.3125 -0.0325 0.020 Uiso 1 1 calc R U . . .
C3 C 0.2041(6) 0.2442(4) 0.1426(3) 0.0185(5) Uani 1 1 d . . . . .
H3A H 0.4161 0.2960 0.1726 0.022 Uiso 1 1 calc R U . . .
H3B H 0.1392 0.0771 0.1115 0.022 Uiso 1 1 calc R U . . .
C4 C 0.0991(5) 0.2978(4) 0.2953(3) 0.0172(5) Uani 1 1 d . . . . .
C5 C 0.6783(6) -0.2373(5) -0.2628(3) 0.0220(5) Uani 1 1 d . . . . .
H5 H 0.6866 -0.2629 -0.1487 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7344(6) -0.2554(5) -0.5212(4) 0.0237(6) Uani 1 1 d . . . . .
H6 H 0.7896 -0.2971 -0.6193 0.028 Uiso 1 1 calc R U . . .
C7 C 0.5872(6) -0.1068(5) -0.5052(4) 0.0244(6) Uani 1 1 d . . . . .
H7 H 0.5195 -0.0238 -0.5902 0.029 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 C2 1.820(2) . ?
O1 C1 1.234(3) . ?
O2 C1 1.261(3) . ?
O3 C4 1.319(3) . ?
O3 H22 0.83(2) . ?
O4 C4 1.210(3) . ?
N1 C5 1.324(4) . ?
N1 C7 1.374(4) . ?
N1 H20 0.83(2) . ?
N2 C5 1.318(4) . ?
N2 C6 1.376(4) . ?
N2 H21 0.8800 . ?
C1 C2 1.545(3) . ?
C2 C3 1.509(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.513(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5 0.9500 . ?
C6 C7 1.353(4) . ?
C6 H6 0.9500 . ?
C7 H7 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
C4 O3 H22 109(2) . . ?
C5 N1 C7 108.6(2) . . ?
C5 N1 H20 125(2) . . ?
C7 N1 H20 126(2) . . ?
C5 N2 C6 109.0(2) . . ?
C5 N2 H21 125.5 . . ?
C6 N2 H21 125.5 . . ?
O1 C1 O2 126.3(2) . . ?
O1 C1 C2 117.9(2) . . ?
O2 C1 C2 115.9(2) . . ?
C3 C2 C1 113.8(2) . . ?
C3 C2 Cl1 109.65(17) . . ?
C1 C2 Cl1 106.55(17) . . ?
C3 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
Cl1 C2 H2 108.9 . . ?
C2 C3 C4 113.6(2) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O4 C4 O3 124.0(2) . . ?
O4 C4 C3 124.1(2) . . ?
O3 C4 C3 111.8(2) . . ?
N2 C5 N1 108.8(2) . . ?
N2 C5 H5 125.6 . . ?
N1 C5 H5 125.6 . . ?
C7 C6 N2 106.5(2) . . ?
C7 C6 H6 126.7 . . ?
N2 C6 H6 126.7 . . ?
C6 C7 N1 107.1(3) . . ?
C6 C7 H7 126.5 . . ?
N1 C7 H7 126.5 . . ?

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
O1 C1 C2 C3 -5.5(3) . . . . ?
O2 C1 C2 C3 174.3(2) . . . . ?
O1 C1 C2 Cl1 115.4(2) . . . . ?
O2 C1 C2 Cl1 -64.8(3) . . . . ?
C1 C2 C3 C4 -175.6(2) . . . . ?
Cl1 C2 C3 C4 65.3(2) . . . . ?
C2 C3 C4 O4 15.3(4) . . . . ?
C2 C3 C4 O3 -165.9(2) . . . . ?
C6 N2 C5 N1 0.1(3) . . . . ?
C7 N1 C5 N2 -0.2(3) . . . . ?
C5 N2 C6 C7 0.0(3) . . . . ?
N2 C6 C7 N1 -0.1(3) . . . . ?
C5 N1 C7 C6 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
N1 H20 O1 0.83(2) 1.92(2) 2.735(3) 166(4) .
O3 H22 O2 0.83(2) 1.77(2) 2.595(2) 176(4) 1_556
N2 H21 O2 0.88(2) 1.87(2) 2.752(3) 177(4) 1_645

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.039

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 1-propanol
####################################################################### 
# 
# 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_15kaw05a
_database_code_depnum_ccdc_archive 'CCDC 1470680'
_audit_update_record             
;
2016-03-25 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

# Q (+)-1/(-)-2 Im


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          398-400
_chemical_formula_moiety         'C4 H4 Br O4, C4 H4 Cl O4, 2(C3 H5 N2)'
_chemical_formula_sum            'C14 H18 Br Cl N4 O8'
_chemical_formula_weight         485.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   8.1185(8)
_cell_length_b                   8.2996(8)
_cell_length_c                   8.8998(9)
_cell_angle_alpha                100.911(5)
_cell_angle_beta                 106.931(5)
_cell_angle_gamma                117.952(4)
_cell_volume                     467.58(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6774
_cell_measurement_theta_min      5.63
_cell_measurement_theta_max      68.11

_exptl_crystal_description       'transparent prism'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_F_000             246
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    4.798
_shelx_estimated_absorpt_T_min   0.471
_shelx_estimated_absorpt_T_max   0.669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10562
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.631
_diffrn_reflns_theta_max         68.230
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2949
_reflns_number_gt                2936
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.980

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to oxygen and nitrogen
 were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with O-H and N-H bond distances restrained to 0.85(2) angstroms.

 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.4507P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2949
_refine_ls_number_parameters     272
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.140
_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 0.22327(8) 0.04752(8) 0.51218(7) 0.02766(18) Uani 1 1 d . . . . .
Cl1 Cl -0.3728(2) -0.3526(2) 1.18585(16) 0.0239(3) Uani 1 1 d . . . . .
O1 O -0.6882(7) -0.2595(7) 0.9949(6) 0.0278(10) Uani 1 1 d . . . . .
O2 O -0.7586(7) -0.4977(6) 0.7706(5) 0.0243(9) Uani 1 1 d . . . . .
O3 O 0.0115(7) -0.1409(7) 1.0783(6) 0.0229(9) Uani 1 1 d . . . . .
O4 O -0.0807(8) -0.4169(9) 0.8772(6) 0.0273(10) Uani 1 1 d D . . . .
H20 H 0.047(5) -0.370(11) 0.924(9) 0.033 Uiso 1 1 d D U . . .
O5 O 0.5359(7) -0.0536(7) 0.7108(6) 0.0295(10) Uani 1 1 d . . . . .
O6 O 0.6080(6) 0.1832(6) 0.9375(5) 0.0213(9) Uani 1 1 d . . . . .
O7 O -0.1664(9) -0.1741(8) 0.6269(7) 0.0236(11) Uani 1 1 d . . . . .
O8 O -0.0774(8) 0.0974(7) 0.8266(7) 0.0257(11) Uani 1 1 d D . . . .
H21 H -0.207(5) 0.042(10) 0.777(9) 0.031 Uiso 1 1 d D U . . .
N1 N -0.4187(9) 0.0704(8) 1.2879(7) 0.0210(11) Uani 1 1 d D . . . .
H22 H -0.505(11) -0.036(8) 1.200(8) 0.025 Uiso 1 1 d D U . . .
N2 N -0.1595(8) 0.2966(8) 1.5253(6) 0.0211(11) Uani 1 1 d D . . . .
H23 H -0.058(7) 0.346(9) 1.618(5) 0.025 Uiso 1 1 d D U . . .
N3 N 0.2687(8) -0.3810(8) 0.4124(6) 0.0202(11) Uani 1 1 d D . . . .
H24 H 0.342(10) -0.273(6) 0.492(7) 0.024 Uiso 1 1 d D U . . .
N4 N 0.0071(8) -0.6140(8) 0.1765(7) 0.0198(10) Uani 1 1 d D . . . .
H25 H -0.115(6) -0.672(9) 0.104(7) 0.024 Uiso 1 1 d D U . . .
C1 C -0.6409(9) -0.3580(8) 0.9080(8) 0.0181(12) Uani 1 1 d . . . . .
C2 C -0.4132(9) -0.2911(9) 0.9936(8) 0.0216(13) Uani 1 1 d . . . . .
H2 H -0.3224 -0.1445 1.0302 0.026 Uiso 1 1 calc R U . . .
C3 C -0.3505(10) -0.3862(10) 0.8801(8) 0.0248(13) Uani 1 1 d . . . . .
H3A H -0.3902 -0.3693 0.7709 0.030 Uiso 1 1 calc R U . . .
H3B H -0.4278 -0.5298 0.8551 0.030 Uiso 1 1 calc R U . . .
C4 C -0.1195(9) -0.3002(9) 0.9586(8) 0.0192(12) Uani 1 1 d . . . . .
C5 C -0.2581(11) 0.1099(10) 1.4203(8) 0.0247(13) Uani 1 1 d . . . . .
H5 H -0.2199 0.0203 1.4373 0.030 Uiso 1 1 calc R U . . .
C6 C -0.2629(11) 0.3780(10) 1.4569(8) 0.0213(13) Uani 1 1 d . . . . .
H6 H -0.2272 0.5085 1.5066 0.026 Uiso 1 1 calc R U . . .
C7 C -0.4214(12) 0.2393(11) 1.3087(9) 0.0230(15) Uani 1 1 d . . . . .
H7 H -0.5182 0.2531 1.2315 0.028 Uiso 1 1 calc R U . . .
C8 C -0.0355(11) -0.0183(11) 0.7471(8) 0.0206(13) Uani 1 1 d . . . . .
C9 C 0.1962(10) 0.0663(9) 0.8276(8) 0.0234(13) Uani 1 1 d . . . . .
H9A H 0.2750 0.2108 0.8569 0.028 Uiso 1 1 calc R U . . .
H9B H 0.2330 0.0444 0.9346 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2601(10) -0.0236(10) 0.7140(8) 0.0223(13) Uani 1 1 d . . . . .
H10 H 0.1698 -0.1707 0.6749 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4889(9) 0.0438(9) 0.7954(8) 0.0216(12) Uani 1 1 d . . . . .
C12 C 0.1010(11) -0.4277(10) 0.2825(8) 0.0228(13) Uani 1 1 d . . . . .
H12 H 0.0553 -0.3429 0.2674 0.027 Uiso 1 1 calc R U . . .
C13 C 0.1181(10) -0.6880(10) 0.2408(8) 0.0223(13) Uani 1 1 d . . . . .
H13 H 0.0864 -0.8171 0.1921 0.027 Uiso 1 1 calc R U . . .
C14 C 0.2848(10) -0.5384(10) 0.3899(8) 0.0244(14) Uani 1 1 d . . . . .
H14 H 0.3915 -0.5441 0.4636 0.029 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
Br1 C10 1.980(6) . ?
Cl1 C2 1.859(7) . ?
O1 C1 1.282(7) . ?
O2 C1 1.223(7) . ?
O3 C4 1.226(8) . ?
O4 C4 1.309(8) . ?
O4 H20 0.84(3) . ?
O5 C11 1.262(7) . ?
O6 C11 1.248(7) . ?
O7 C8 1.213(9) . ?
O8 C8 1.314(8) . ?
O8 H21 0.84(3) . ?
N1 C5 1.324(9) . ?
N1 C7 1.391(9) . ?
N1 H22 0.85(3) . ?
N2 C5 1.330(8) . ?
N2 C6 1.387(8) . ?
N2 H23 0.83(3) . ?
N3 C12 1.326(9) . ?
N3 C14 1.357(9) . ?
N3 H24 0.82(3) . ?
N4 C12 1.336(8) . ?
N4 C13 1.367(8) . ?
N4 H25 0.83(3) . ?
C1 C2 1.537(8) . ?
C2 C3 1.509(8) . ?
C2 H2 1.0000 . ?
C3 C4 1.519(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5 0.9500 . ?
C6 C7 1.330(10) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.527(9) . ?
C9 C10 1.493(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.542(9) . ?
C10 H10 1.0000 . ?
C12 H12 0.9500 . ?
C13 C14 1.375(9) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O4 H20 110(5) . . ?
C8 O8 H21 107(5) . . ?
C5 N1 C7 108.7(6) . . ?
C5 N1 H22 128(7) . . ?
C7 N1 H22 123(7) . . ?
C5 N2 C6 108.7(6) . . ?
C5 N2 H23 122(5) . . ?
C6 N2 H23 129(5) . . ?
C12 N3 C14 109.0(5) . . ?
C12 N3 H24 121(6) . . ?
C14 N3 H24 130(6) . . ?
C12 N4 C13 108.8(5) . . ?
C12 N4 H25 118(5) . . ?
C13 N4 H25 130(5) . . ?
O2 C1 O1 126.5(6) . . ?
O2 C1 C2 119.4(5) . . ?
O1 C1 C2 114.1(5) . . ?
C3 C2 C1 113.8(5) . . ?
C3 C2 Cl1 109.0(4) . . ?
C1 C2 Cl1 108.0(4) . . ?
C3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
Cl1 C2 H2 108.6 . . ?
C2 C3 C4 113.1(5) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O3 C4 O4 125.3(6) . . ?
O3 C4 C3 124.2(6) . . ?
O4 C4 C3 110.5(5) . . ?
N1 C5 N2 108.2(6) . . ?
N1 C5 H5 125.9 . . ?
N2 C5 H5 125.9 . . ?
C7 C6 N2 107.2(6) . . ?
C7 C6 H6 126.4 . . ?
N2 C6 H6 126.4 . . ?
C6 C7 N1 107.1(6) . . ?
C6 C7 H7 126.4 . . ?
N1 C7 H7 126.4 . . ?
O7 C8 O8 123.7(6) . . ?
O7 C8 C9 124.8(6) . . ?
O8 C8 C9 111.5(6) . . ?
C10 C9 C8 113.1(5) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 115.0(5) . . ?
C9 C10 Br1 110.1(4) . . ?
C11 C10 Br1 105.5(4) . . ?
C9 C10 H10 108.7 . . ?
C11 C10 H10 108.7 . . ?
Br1 C10 H10 108.7 . . ?
O6 C11 O5 126.2(6) . . ?
O6 C11 C10 118.5(5) . . ?
O5 C11 C10 115.3(5) . . ?
N3 C12 N4 108.6(5) . . ?
N3 C12 H12 125.7 . . ?
N4 C12 H12 125.7 . . ?
N4 C13 C14 106.3(5) . . ?
N4 C13 H13 126.9 . . ?
C14 C13 H13 126.9 . . ?
N3 C14 C13 107.3(6) . . ?
N3 C14 H14 126.3 . . ?
C13 C14 H14 126.3 . . ?

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
O2 C1 C2 C3 10.4(8) . . . . ?
O1 C1 C2 C3 -171.3(6) . . . . ?
O2 C1 C2 Cl1 -110.8(6) . . . . ?
O1 C1 C2 Cl1 67.5(6) . . . . ?
C1 C2 C3 C4 172.9(5) . . . . ?
Cl1 C2 C3 C4 -66.5(6) . . . . ?
C2 C3 C4 O3 -17.6(9) . . . . ?
C2 C3 C4 O4 164.3(5) . . . . ?
C7 N1 C5 N2 0.6(8) . . . . ?
C6 N2 C5 N1 0.4(7) . . . . ?
C5 N2 C6 C7 -1.2(7) . . . . ?
N2 C6 C7 N1 1.5(7) . . . . ?
C5 N1 C7 C6 -1.3(8) . . . . ?
O7 C8 C9 C10 18.7(9) . . . . ?
O8 C8 C9 C10 -162.5(5) . . . . ?
C8 C9 C10 C11 -174.9(5) . . . . ?
C8 C9 C10 Br1 66.1(6) . . . . ?
C9 C10 C11 O6 -9.1(8) . . . . ?
Br1 C10 C11 O6 112.4(6) . . . . ?
C9 C10 C11 O5 169.3(6) . . . . ?
Br1 C10 C11 O5 -69.2(6) . . . . ?
C14 N3 C12 N4 0.5(8) . . . . ?
C13 N4 C12 N3 0.0(7) . . . . ?
C12 N4 C13 C14 -0.5(7) . . . . ?
C12 N3 C14 C13 -0.7(8) . . . . ?
N4 C13 C14 N3 0.7(7) . . . . ?

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
N3 H24 O5 0.82(3) 1.94(3) 2.744(7) 165(8) .
N1 H22 O1 0.85(3) 1.88(3) 2.728(7) 175(9) .
O4 H20 O1 0.84(3) 1.73(3) 2.568(7) 171(8) 1_655
O8 H21 O5 0.84(3) 1.70(3) 2.535(7) 170(8) 1_455
N4 H25 O6 0.83(3) 1.88(3) 2.715(7) 177(7) 1_444
N2 H23 O2 0.83(3) 1.97(4) 2.741(7) 154(6) 1_666

_refine_diff_density_max         0.689
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.090

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method methanol:acetone
####################################################################### 
# 
# 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_15kaw14a
_database_code_depnum_ccdc_archive 'CCDC 1470681'
_audit_update_record             
;
2016-03-25 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

# (+)-1/(-)-2 BPNO

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          456-458
_chemical_formula_moiety         '2(C10 H8 N2 O2), C4 H5 Br O4, C4 H5'
_chemical_formula_sum            'C28 H26 Br Cl N4 O12'
_chemical_formula_weight         725.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   7.7692(3)
_cell_length_b                   9.6937(5)
_cell_length_c                   10.7311(4)
_cell_angle_alpha                102.275(3)
_cell_angle_beta                 93.038(2)
_cell_angle_gamma                107.620(3)
_cell_volume                     746.66(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7996
_cell_measurement_theta_min      4.25
_cell_measurement_theta_max      68.06

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             370
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.337
_shelx_estimated_absorpt_T_min   0.626
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16717
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.250
_diffrn_reflns_theta_max         68.223
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_point_group_measured_fraction_full 0.871
_reflns_number_total             4755
_reflns_number_gt                4597
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_max     0.759
_reflns_Friedel_fraction_full    0.764

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to oxygen and nitrogen
 were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with O-H and N-H bond distances restrained to 0.85(2) angstroms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+0.0865P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1797 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(18)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4755
_refine_ls_number_parameters     458
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0803
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.18827(12) 0.32989(10) 0.45237(8) 0.02424(17) Uani 0.85 1 d D . P A 1
Cl1 Cl 0.8117(2) 0.66996(19) 0.54753(14) 0.0244(3) Uani 0.85 1 d D . P B 1
O1 O 0.5361(6) 0.4733(5) 0.2971(4) 0.0363(11) Uani 1 1 d D . . . .
H1 H 0.553(9) 0.415(6) 0.230(4) 0.044 Uiso 1 1 d D U . . .
N1 N 0.4040(5) 0.1683(4) 0.0344(4) 0.0156(8) Uani 1 1 d . . . . .
C1 C 0.6342(9) 0.6132(8) 0.3061(6) 0.0240(14) Uani 1 1 d D . . . .
O2 O 0.7150(5) 0.6579(4) 0.2218(4) 0.0260(9) Uani 1 1 d . . . . .
N2 N -0.1766(6) -0.5776(5) -0.1892(4) 0.0202(10) Uani 1 1 d . . . . .
C2 C 0.6513(9) 0.7104(7) 0.4409(6) 0.0201(13) Uani 0.85 1 d D . P B 1
H2 H 0.5295 0.6851 0.4725 0.024 Uiso 0.85 1 calc R U P B 1
O3 O 0.8108(7) 1.1029(6) 0.5974(5) 0.0368(12) Uani 1 1 d D . . . .
H3 H 0.785(10) 1.154(7) 0.664(4) 0.044 Uiso 1 1 d D U . . .
N3 N 1.1803(6) 1.5747(5) 1.1943(4) 0.0201(9) Uani 1 1 d . . . . .
C3 C 0.7153(9) 0.8728(7) 0.4427(7) 0.0202(14) Uani 0.85 1 d D . P B 1
H3A H 0.6476 0.8893 0.3695 0.024 Uiso 0.85 1 calc R U P B 1
H3B H 0.8460 0.9036 0.4315 0.024 Uiso 0.85 1 calc R U P B 1
O4 O 0.5626(5) 0.9310(4) 0.6293(3) 0.0252(8) Uani 1 1 d . . . . .
C4 C 0.6886(7) 0.9705(6) 0.5685(5) 0.0224(12) Uani 1 1 d D . . . .
O5 O 0.4777(6) 0.5245(4) 0.7106(4) 0.0315(9) Uani 1 1 d D . . . .
H5 H 0.497(8) 0.578(6) 0.788(3) 0.038 Uiso 1 1 d D U . . .
N5 N 0.6016(5) 0.8283(5) 0.9723(4) 0.0162(8) Uani 1 1 d . . . . .
C5 C 0.3737(7) 0.3860(6) 0.7019(5) 0.0220(11) Uani 1 1 d D . . . .
O6 O 0.2903(5) 0.3408(4) 0.7840(3) 0.0237(8) Uani 1 1 d . . . . .
C6 C 0.3601(8) 0.2848(7) 0.5685(5) 0.0204(14) Uani 0.85 1 d D . P A 1
H6 H 0.4826 0.3098 0.5378 0.024 Uiso 0.85 1 calc R U P A 1
O7 O 0.1962(5) -0.1093(5) 0.4120(4) 0.0353(10) Uani 1 1 d D . . . .
H7 H 0.229(9) -0.172(6) 0.357(5) 0.042 Uiso 1 1 d D U . . .
C7 C 0.2941(8) 0.1212(7) 0.5670(6) 0.0179(12) Uani 0.85 1 d D . P A 1
H7A H 0.1636 0.0911 0.5790 0.022 Uiso 0.85 1 calc R U P A 1
H7B H 0.3625 0.1037 0.6393 0.022 Uiso 0.85 1 calc R U P A 1
O8 O 0.4445(5) 0.0636(4) 0.3784(3) 0.0225(8) Uani 1 1 d . . . . .
C8 C 0.3192(7) 0.0249(6) 0.4394(5) 0.0233(11) Uani 1 1 d D . . . .
O9 O 0.5189(5) 0.3058(4) 0.0743(3) 0.0204(8) Uani 1 1 d . . . . .
C9 C 0.3977(6) 0.0934(6) -0.0895(4) 0.0175(10) Uani 1 1 d . . . . .
H9 H 0.4720 0.1416 -0.1453 0.021 Uiso 1 1 calc R U . . .
O10 O -0.2894(5) -0.7163(4) -0.2324(4) 0.0330(9) Uani 1 1 d . . . . .
C10 C 0.2840(6) -0.0525(5) -0.1349(4) 0.0162(10) Uani 1 1 d . . . . .
H10 H 0.2801 -0.1030 -0.2217 0.019 Uiso 1 1 calc R U . . .
O11 O 0.4863(5) 0.6910(4) 0.9325(3) 0.0215(8) Uani 1 1 d . . . . .
C11 C 0.1737(6) -0.1264(5) -0.0528(4) 0.0152(10) Uani 1 1 d . . . . .
O12 O 1.2925(5) 1.7133(4) 1.2380(4) 0.0339(10) Uani 1 1 d . . . . .
C12 C 0.1829(7) -0.0435(6) 0.0736(5) 0.0178(10) Uani 1 1 d . . . . .
H12 H 0.1092 -0.0883 0.1313 0.021 Uiso 1 1 calc R U . . .
C13 C 0.2975(8) 0.1023(6) 0.1151(5) 0.0173(12) Uani 1 1 d . . . . .
H13 H 0.3015 0.1563 0.2007 0.021 Uiso 1 1 calc R U . . .
C14 C -0.0385(7) -0.5219(6) -0.2547(5) 0.0197(10) Uani 1 1 d . . . . .
H14 H -0.0207 -0.5833 -0.3314 0.024 Uiso 1 1 calc R U . . .
C15 C 0.0781(7) -0.3761(6) -0.2114(5) 0.0173(12) Uani 1 1 d . . . . .
H15 H 0.1750 -0.3391 -0.2583 0.021 Uiso 1 1 calc R U . . .
C16 C 0.0535(6) -0.2834(5) -0.0993(4) 0.0156(10) Uani 1 1 d . . . . .
C17 C -0.0906(6) -0.3462(6) -0.0331(5) 0.0173(10) Uani 1 1 d . . . . .
H17 H -0.1104 -0.2876 0.0444 0.021 Uiso 1 1 calc R U . . .
C18 C -0.2038(7) -0.4915(6) -0.0789(5) 0.0207(11) Uani 1 1 d . . . . .
H18 H -0.3009 -0.5316 -0.0333 0.025 Uiso 1 1 calc R U . . .
C19 C 1.2094(7) 1.4881(6) 1.0849(5) 0.0210(11) Uani 1 1 d . . . . .
H19 H 1.3067 1.5280 1.0393 0.025 Uiso 1 1 calc R U . . .
C20 C 1.0968(7) 1.3414(6) 1.0399(5) 0.0176(10) Uani 1 1 d . . . . .
H20 H 1.1185 1.2813 0.9641 0.021 Uiso 1 1 calc R U . . .
C21 C 0.9513(7) 1.2810(5) 1.1052(4) 0.0148(10) Uani 1 1 d . . . . .
C22 C 0.9246(6) 1.3762(6) 1.2164(5) 0.0171(11) Uani 1 1 d . . . . .
H22 H 0.8259 1.3401 1.2622 0.020 Uiso 1 1 calc R U . . .
C23 C 1.0382(6) 1.5191(6) 1.2588(5) 0.0191(11) Uani 1 1 d . . . . .
H23 H 1.0184 1.5810 1.3344 0.023 Uiso 1 1 calc R U . . .
C24 C 0.7096(7) 0.8947(6) 0.8920(5) 0.0189(11) Uani 1 1 d . . . . .
H24 H 0.7064 0.8406 0.8065 0.023 Uiso 1 1 calc R U . . .
C25 C 0.8239(6) 1.0401(6) 0.9336(4) 0.0183(10) Uani 1 1 d . . . . .
H25 H 0.8988 1.0846 0.8762 0.022 Uiso 1 1 calc R U . . .
C26 C 0.8314(6) 1.1232(6) 1.0588(4) 0.0148(10) Uani 1 1 d . . . . .
C27 C 0.7202(7) 1.0493(6) 1.1391(4) 0.0181(10) Uani 1 1 d . . . . .
H27 H 0.7234 1.1007 1.2255 0.022 Uiso 1 1 calc R U . . .
C28 C 0.6062(6) 0.9038(6) 1.0961(5) 0.0170(10) Uani 1 1 d . . . . .
H28 H 0.5315 0.8566 1.1523 0.020 Uiso 1 1 calc R U . . .
Br1A Br 0.1166(7) 0.2359(8) 0.4205(4) 0.0370(11) Uani 0.15 1 d D . P A 2
Cl1A Cl 0.8796(11) 0.7601(12) 0.5849(7) 0.0217(18) Uani 0.15 1 d D . P B 2
C2A C 0.743(3) 0.840(3) 0.496(2) 0.0201(13) Uani 0.15 1 d D . P B 2
H2A H 0.8186 0.8789 0.4308 0.024 Uiso 0.15 1 calc R U P B 2
C3A C 0.580(4) 0.718(3) 0.421(3) 0.0202(14) Uani 0.15 1 d D . P B 2
H3A1 H 0.4939 0.7616 0.3860 0.024 Uiso 0.15 1 calc R U P B 2
H3A2 H 0.5172 0.6573 0.4787 0.024 Uiso 0.15 1 calc R U P B 2
C6A C 0.268(4) 0.155(3) 0.520(2) 0.0204(14) Uani 0.15 1 d D . P A 2
H6A H 0.1983 0.1177 0.5886 0.024 Uiso 0.15 1 calc R U P A 2
C7A C 0.424(4) 0.291(3) 0.584(3) 0.0179(12) Uani 0.15 1 d D . P A 2
H7A1 H 0.4626 0.3527 0.5209 0.022 Uiso 0.15 1 calc R U P A 2
H7A2 H 0.5285 0.2614 0.6108 0.022 Uiso 0.15 1 calc R U P A 2


_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 C6 1.984(6) . ?
Cl1 C2 1.831(7) . ?
O1 C1 1.319(8) . ?
O1 H1 0.86(3) . ?
N1 O9 1.324(5) . ?
N1 C13 1.355(7) . ?
N1 C9 1.363(6) . ?
C1 O2 1.209(7) . ?
C1 C2 1.524(9) . ?
C1 C3A 1.58(2) . ?
N2 O10 1.330(5) . ?
N2 C14 1.352(6) . ?
N2 C18 1.362(6) . ?
C2 C3 1.496(9) . ?
C2 H2 1.0000 . ?
O3 C4 1.307(7) . ?
O3 H3 0.85(3) . ?
N3 O12 1.328(5) . ?
N3 C19 1.363(7) . ?
N3 C23 1.367(6) . ?
C3 C4 1.538(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
O4 C4 1.216(7) . ?
C4 C2A 1.52(2) . ?
O5 C5 1.321(7) . ?
O5 H5 0.86(3) . ?
N5 O11 1.324(5) . ?
N5 C24 1.359(6) . ?
N5 C28 1.367(6) . ?
C5 O6 1.201(6) . ?
C5 C6 1.532(7) . ?
C5 C7A 1.543(8) . ?
C6 C7 1.508(8) . ?
C6 H6 1.0000 . ?
O7 C8 1.322(6) . ?
O7 H7 0.86(3) . ?
C7 C8 1.542(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O8 C8 1.212(6) . ?
C8 C6A 1.54(2) . ?
C9 C10 1.386(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.414(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.408(6) . ?
C11 C16 1.485(6) . ?
C12 C13 1.384(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.391(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.400(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.409(7) . ?
C17 C18 1.382(7) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.389(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.403(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.411(7) . ?
C21 C26 1.490(7) . ?
C22 C23 1.362(7) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.381(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.401(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.403(7) . ?
C27 C28 1.382(7) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
Br1A C6A 1.985(7) . ?
Cl1A C2A 1.832(7) . ?
C2A C3A 1.495(9) . ?
C2A H2A 1.0000 . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C6A C7A 1.50(2) . ?
C6A H6A 1.0000 . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?

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
C1 O1 H1 111(4) . . ?
O9 N1 C13 121.0(4) . . ?
O9 N1 C9 118.4(4) . . ?
C13 N1 C9 120.6(4) . . ?
O2 C1 O1 124.6(6) . . ?
O2 C1 C2 123.1(6) . . ?
O1 C1 C2 112.0(5) . . ?
O2 C1 C3A 123.5(14) . . ?
O1 C1 C3A 109.2(13) . . ?
O10 N2 C14 120.6(4) . . ?
O10 N2 C18 119.0(4) . . ?
C14 N2 C18 120.4(4) . . ?
C3 C2 C1 111.8(5) . . ?
C3 C2 Cl1 109.7(4) . . ?
C1 C2 Cl1 108.8(4) . . ?
C3 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
Cl1 C2 H2 108.8 . . ?
C4 O3 H3 108(5) . . ?
O12 N3 C19 119.2(4) . . ?
O12 N3 C23 120.4(4) . . ?
C19 N3 C23 120.4(4) . . ?
C2 C3 C4 112.5(5) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
O4 C4 O3 124.4(5) . . ?
O4 C4 C2A 112.4(12) . . ?
O3 C4 C2A 118.1(12) . . ?
O4 C4 C3 123.6(5) . . ?
O3 C4 C3 111.9(5) . . ?
C5 O5 H5 112(4) . . ?
O11 N5 C24 121.3(4) . . ?
O11 N5 C28 118.2(4) . . ?
C24 N5 C28 120.5(4) . . ?
O6 C5 O5 126.2(5) . . ?
O6 C5 C6 121.6(5) . . ?
O5 C5 C6 112.2(5) . . ?
O6 C5 C7A 126.6(15) . . ?
O5 C5 C7A 105.2(14) . . ?
C7 C6 C5 113.1(5) . . ?
C7 C6 Br1 109.8(4) . . ?
C5 C6 Br1 106.8(4) . . ?
C7 C6 H6 109.0 . . ?
C5 C6 H6 109.0 . . ?
Br1 C6 H6 109.0 . . ?
C8 O7 H7 111(5) . . ?
C6 C7 C8 111.5(5) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
O8 C8 O7 124.6(5) . . ?
O8 C8 C6A 114.0(12) . . ?
O7 C8 C6A 117.8(12) . . ?
O8 C8 C7 124.0(5) . . ?
O7 C8 C7 111.1(4) . . ?
N1 C9 C10 120.7(4) . . ?
N1 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 120.4(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 116.7(4) . . ?
C12 C11 C16 122.2(4) . . ?
C10 C11 C16 121.1(4) . . ?
C13 C12 C11 121.1(5) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
N1 C13 C12 120.4(5) . . ?
N1 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
N2 C14 C15 120.9(5) . . ?
N2 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C16 120.5(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 116.8(4) . . ?
C15 C16 C11 121.4(4) . . ?
C17 C16 C11 121.8(4) . . ?
C18 C17 C16 121.1(4) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
N2 C18 C17 120.3(4) . . ?
N2 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
N3 C19 C20 120.0(5) . . ?
N3 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 120.8(5) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C22 117.0(4) . . ?
C20 C21 C26 121.2(4) . . ?
C22 C21 C26 121.8(4) . . ?
C23 C22 C21 120.9(5) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 N3 120.9(5) . . ?
C22 C23 H23 119.6 . . ?
N3 C23 H23 119.6 . . ?
N5 C24 C25 120.6(4) . . ?
N5 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 121.2(4) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C27 116.3(5) . . ?
C25 C26 C21 122.2(4) . . ?
C27 C26 C21 121.6(4) . . ?
C28 C27 C26 121.9(4) . . ?
C28 C27 H27 119.0 . . ?
C26 C27 H27 119.0 . . ?
N5 C28 C27 119.6(4) . . ?
N5 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C3A C2A C4 111.0(17) . . ?
C3A C2A Cl1A 109.0(17) . . ?
C4 C2A Cl1A 118.8(13) . . ?
C3A C2A H2A 105.7 . . ?
C4 C2A H2A 105.7 . . ?
Cl1A C2A H2A 105.7 . . ?
C2A C3A C1 111.8(19) . . ?
C2A C3A H3A1 109.3 . . ?
C1 C3A H3A1 109.3 . . ?
C2A C3A H3A2 109.3 . . ?
C1 C3A H3A2 109.3 . . ?
H3A1 C3A H3A2 107.9 . . ?
C7A C6A C8 115.9(17) . . ?
C7A C6A Br1A 102.2(19) . . ?
C8 C6A Br1A 114.2(12) . . ?
C7A C6A H6A 108.0 . . ?
C8 C6A H6A 108.0 . . ?
Br1A C6A H6A 108.0 . . ?
C6A C7A C5 112.1(18) . . ?
C6A C7A H7A1 109.2 . . ?
C5 C7A H7A1 109.2 . . ?
C6A C7A H7A2 109.2 . . ?
C5 C7A H7A2 109.2 . . ?
H7A1 C7A H7A2 107.9 . . ?

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
O2 C1 C2 C3 22.0(8) . . . . ?
O1 C1 C2 C3 -163.9(5) . . . . ?
O2 C1 C2 Cl1 -99.3(6) . . . . ?
O1 C1 C2 Cl1 74.8(6) . . . . ?
C1 C2 C3 C4 165.9(5) . . . . ?
Cl1 C2 C3 C4 -73.4(6) . . . . ?
C2 C3 C4 O4 -33.4(8) . . . . ?
C2 C3 C4 O3 150.3(6) . . . . ?
O6 C5 C6 C7 -20.9(8) . . . . ?
O5 C5 C6 C7 162.0(5) . . . . ?
O6 C5 C6 Br1 100.0(6) . . . . ?
O5 C5 C6 Br1 -77.1(5) . . . . ?
C5 C6 C7 C8 -168.4(5) . . . . ?
Br1 C6 C7 C8 72.4(5) . . . . ?
C6 C7 C8 O8 34.0(7) . . . . ?
C6 C7 C8 O7 -151.6(5) . . . . ?
O9 N1 C9 C10 177.9(4) . . . . ?
C13 N1 C9 C10 -0.9(7) . . . . ?
N1 C9 C10 C11 -0.6(7) . . . . ?
C9 C10 C11 C12 1.6(6) . . . . ?
C9 C10 C11 C16 -179.0(4) . . . . ?
C10 C11 C12 C13 -1.3(7) . . . . ?
C16 C11 C12 C13 179.3(4) . . . . ?
O9 N1 C13 C12 -177.6(4) . . . . ?
C9 N1 C13 C12 1.2(7) . . . . ?
C11 C12 C13 N1 -0.1(7) . . . . ?
O10 N2 C14 C15 178.9(5) . . . . ?
C18 N2 C14 C15 -0.2(8) . . . . ?
N2 C14 C15 C16 -0.5(8) . . . . ?
C14 C15 C16 C17 1.2(7) . . . . ?
C14 C15 C16 C11 -178.7(4) . . . . ?
C12 C11 C16 C15 -163.5(5) . . . . ?
C10 C11 C16 C15 17.1(7) . . . . ?
C12 C11 C16 C17 16.6(7) . . . . ?
C10 C11 C16 C17 -162.8(4) . . . . ?
C15 C16 C17 C18 -1.2(7) . . . . ?
C11 C16 C17 C18 178.6(4) . . . . ?
O10 N2 C18 C17 -178.9(4) . . . . ?
C14 N2 C18 C17 0.2(8) . . . . ?
C16 C17 C18 N2 0.5(7) . . . . ?
O12 N3 C19 C20 178.0(4) . . . . ?
C23 N3 C19 C20 -1.4(8) . . . . ?
N3 C19 C20 C21 0.6(8) . . . . ?
C19 C20 C21 C22 0.7(7) . . . . ?
C19 C20 C21 C26 -179.1(4) . . . . ?
C20 C21 C22 C23 -1.3(7) . . . . ?
C26 C21 C22 C23 178.5(4) . . . . ?
C21 C22 C23 N3 0.6(8) . . . . ?
O12 N3 C23 C22 -178.6(5) . . . . ?
C19 N3 C23 C22 0.8(8) . . . . ?
O11 N5 C24 C25 177.4(4) . . . . ?
C28 N5 C24 C25 -0.9(8) . . . . ?
N5 C24 C25 C26 -0.2(8) . . . . ?
C24 C25 C26 C27 1.4(7) . . . . ?
C24 C25 C26 C21 -179.0(4) . . . . ?
C20 C21 C26 C25 -17.5(7) . . . . ?
C22 C21 C26 C25 162.7(5) . . . . ?
C20 C21 C26 C27 162.1(5) . . . . ?
C22 C21 C26 C27 -17.8(7) . . . . ?
C25 C26 C27 C28 -1.6(7) . . . . ?
C21 C26 C27 C28 178.8(4) . . . . ?
O11 N5 C28 C27 -177.6(4) . . . . ?
C24 N5 C28 C27 0.8(7) . . . . ?
C26 C27 C28 N5 0.5(7) . . . . ?
O4 C4 C2A C3A 50(2) . . . . ?
O3 C4 C2A C3A -154.6(17) . . . . ?
O4 C4 C2A Cl1A -77.9(19) . . . . ?
O3 C4 C2A Cl1A 78(2) . . . . ?
C4 C2A C3A C1 157.7(19) . . . . ?
Cl1A C2A C3A C1 -70(3) . . . . ?
O2 C1 C3A C2A -58(3) . . . . ?
O1 C1 C3A C2A 139.9(18) . . . . ?
O8 C8 C6A C7A -39(2) . . . . ?
O7 C8 C6A C7A 161.4(19) . . . . ?
O8 C8 C6A Br1A 79.6(16) . . . . ?
O7 C8 C6A Br1A -80.2(17) . . . . ?
C8 C6A C7A C5 -157(2) . . . . ?
Br1A C6A C7A C5 79(3) . . . . ?
O6 C5 C7A C6A 44(3) . . . . ?
O5 C5 C7A C6A -151(2) . . . . ?

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
O1 H1 O9 0.86(3) 1.73(3) 2.561(5) 160(6) .
O3 H3 O10 0.85(3) 1.75(3) 2.574(6) 163(7) 1_676
O5 H5 O11 0.86(3) 1.72(3) 2.561(5) 166(6) .
O7 H7 O12 0.86(3) 1.71(3) 2.562(5) 175(7) 1_434

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.056




_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method methanol
