# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1473188'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H16 Br N2, B F4, H2 O'
_chemical_formula_sum            'C8 H18 B Br F4 N2 O'
_chemical_formula_weight         324.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.886(2)
_cell_length_b                   10.237(2)
_cell_length_c                   11.376(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.16(3)
_cell_angle_gamma                90
_cell_volume                     1264.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8495
_cell_measurement_theta_min      3.196
_cell_measurement_theta_max      27.484

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_F_000             585
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.286
_shelx_estimated_absorpt_T_min   0.560
_shelx_estimated_absorpt_T_max   0.560
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8495
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.196
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2898
_reflns_number_gt                1948
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0796P)²+0.9850P] 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         2864
_refine_ls_number_parameters     160
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.1692
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_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
B1 B 0.7709(7) 0.5048(5) 0.7548(6) 0.0479(15) Uani 1 1 d . . . . .
Br1 Br 0.98496(5) 0.23858(5) 0.51829(5) 0.0490(2) Uani 1 1 d . . . . .
N1 N 0.7790(4) 0.4747(3) 0.2727(3) 0.0353(9) Uani 1 1 d . . . . .
C7 C 0.8825(4) 0.4045(5) 0.3435(4) 0.0430(12) Uani 1 1 d . . . . .
H7A H 0.9252 0.3486 0.2910 0.052 Uiso 1 1 calc R U . . .
H7B H 0.9410 0.4688 0.3761 0.052 Uiso 1 1 calc R U . . .
N2 N 0.6145(4) 0.5987(4) 0.1460(3) 0.0412(10) Uani 1 1 d . . . . .
C3 C 0.6933(5) 0.3786(5) 0.2086(4) 0.0435(12) Uani 1 1 d . . . . .
H3A H 0.6534 0.3244 0.2645 0.052 Uiso 1 1 calc R U . . .
H3B H 0.7389 0.3224 0.1586 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5963(5) 0.4581(5) 0.1331(5) 0.0499(13) Uani 1 1 d . . . . .
H4A H 0.6003 0.4345 0.0509 0.060 Uiso 1 1 calc R U . . .
H4B H 0.5148 0.4356 0.1560 0.060 Uiso 1 1 calc R U . . .
C6 C 0.7357(5) 0.6318(5) 0.1095(4) 0.0431(12) Uani 1 1 d . . . . .
H6A H 0.7481 0.7254 0.1164 0.052 Uiso 1 1 calc R U . . .
H6B H 0.7406 0.6081 0.0274 0.052 Uiso 1 1 calc R U . . .
C2 C 0.6074(5) 0.6325(5) 0.2702(4) 0.0467(12) Uani 1 1 d . . . . .
H2A H 0.5263 0.6106 0.2942 0.056 Uiso 1 1 calc R U . . .
H2B H 0.6190 0.7259 0.2800 0.056 Uiso 1 1 calc R U . . .
C8 C 0.8394(5) 0.3231(5) 0.4422(4) 0.0476(12) Uani 1 1 d . . . . .
H8A H 0.7806 0.2581 0.4118 0.057 Uiso 1 1 calc R U . . .
H8B H 0.8000 0.3777 0.4982 0.057 Uiso 1 1 calc R U . . .
C5 C 0.8379(5) 0.5605(5) 0.1853(5) 0.0479(13) Uani 1 1 d . . . . .
H5A H 0.8869 0.5078 0.1354 0.057 Uiso 1 1 calc R U . . .
H5B H 0.8917 0.6236 0.2265 0.057 Uiso 1 1 calc R U . . .
C1 C 0.7059(5) 0.5595(5) 0.3501(4) 0.0435(12) Uani 1 1 d . . . . .
H1A H 0.7598 0.6216 0.3926 0.052 Uiso 1 1 calc R U . . .
H1B H 0.6666 0.5062 0.4070 0.052 Uiso 1 1 calc R U . . .
F3 F 0.8594(4) 0.4138(4) 0.7332(4) 0.0853(12) Uani 1 1 d . . . . .
F1 F 0.6999(4) 0.4497(5) 0.8362(4) 0.0993(13) Uani 1 1 d . . . . .
F2 F 0.6990(5) 0.5289(4) 0.6551(4) 0.0978(14) Uani 1 1 d . . . . .
F4 F 0.8219(4) 0.6158(3) 0.7993(4) 0.0985(15) Uani 1 1 d . . . . .
O1 O 0.4859(4) 0.8273(5) 0.0448(4) 0.0756(13) Uani 1 1 d D . . . .
H1WB H 0.543(5) 0.881(4) 0.067(6) 0.091 Uiso 1 1 d D U . . .
H1WA H 0.499(6) 0.754(3) 0.077(7) 0.091 Uiso 1 1 d D 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
B1 F4 1.347(6) . ?
B1 F2 1.354(7) . ?
B1 F1 1.370(8) . ?
B1 F3 1.375(7) . ?
Br1 C8 1.952(5) . ?
N1 C1 1.504(6) . ?
N1 C5 1.505(6) . ?
N1 C3 1.508(6) . ?
N1 C7 1.518(6) . ?
C7 C8 1.501(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N2 C6 1.452(6) . ?
N2 C4 1.459(6) . ?
N2 C2 1.462(6) . ?
C3 C4 1.544(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C5 1.541(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C2 C1 1.547(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O1 H1WB 0.86(2) . ?
O1 H1WA 0.840(19) . ?

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
F4 B1 F2 111.0(5) . . ?
F4 B1 F1 109.3(5) . . ?
F2 B1 F1 108.7(6) . . ?
F4 B1 F3 111.3(6) . . ?
F2 B1 F3 110.1(5) . . ?
F1 B1 F3 106.2(5) . . ?
C1 N1 C5 108.6(4) . . ?
C1 N1 C3 109.0(4) . . ?
C5 N1 C3 109.9(4) . . ?
C1 N1 C7 111.5(4) . . ?
C5 N1 C7 106.9(4) . . ?
C3 N1 C7 110.9(3) . . ?
C8 C7 N1 113.6(4) . . ?
C8 C7 H7A 108.8 . . ?
N1 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
N1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C6 N2 C4 108.7(4) . . ?
C6 N2 C2 109.5(4) . . ?
C4 N2 C2 108.3(4) . . ?
N1 C3 C4 107.4(4) . . ?
N1 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
N1 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
N2 C4 C3 112.5(4) . . ?
N2 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
N2 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N2 C6 C5 111.3(4) . . ?
N2 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N2 C2 C1 111.8(4) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C7 C8 Br1 106.9(3) . . ?
C7 C8 H8A 110.3 . . ?
Br1 C8 H8A 110.3 . . ?
C7 C8 H8B 110.3 . . ?
Br1 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
N1 C5 C6 108.7(4) . . ?
N1 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
N1 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
N1 C1 C2 107.9(4) . . ?
N1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
H1WB O1 H1WA 110(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
C1 N1 C7 C8 56.4(5) . . . . ?
C5 N1 C7 C8 175.0(4) . . . . ?
C3 N1 C7 C8 -65.2(5) . . . . ?
C1 N1 C3 C4 60.4(5) . . . . ?
C5 N1 C3 C4 -58.5(5) . . . . ?
C7 N1 C3 C4 -176.5(4) . . . . ?
C6 N2 C4 C3 59.8(5) . . . . ?
C2 N2 C4 C3 -59.1(6) . . . . ?
N1 C3 C4 N2 -0.4(6) . . . . ?
C4 N2 C6 C5 -60.0(5) . . . . ?
C2 N2 C6 C5 58.1(5) . . . . ?
C6 N2 C2 C1 -59.2(5) . . . . ?
C4 N2 C2 C1 59.2(5) . . . . ?
N1 C7 C8 Br1 178.5(3) . . . . ?
C1 N1 C5 C6 -60.7(5) . . . . ?
C3 N1 C5 C6 58.4(5) . . . . ?
C7 N1 C5 C6 178.9(4) . . . . ?
N2 C6 C5 N1 1.5(6) . . . . ?
C5 N1 C1 C2 59.5(5) . . . . ?
C3 N1 C1 C2 -60.2(5) . . . . ?
C7 N1 C1 C2 177.0(4) . . . . ?
N2 C2 C1 N1 -0.1(6) . . . . ?

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 H1WA N2 0.840(19) 2.14(4) 2.920(6) 154(7) .
O1 H1WB F2 0.86(2) 2.12(3) 2.950(6) 164(6) 4_575
C1 H1B O1 0.97 2.56 3.436(7) 150.5 2_645
C5 H5A Br1 0.97 3.08 3.999(6) 158.6 4_565
C8 H8A F1 0.97 2.43 3.361(7) 159.7 4_565
C6 H6A F2 0.97 2.61 3.538(6) 159.2 4_575
C4 H4B F1 0.97 2.62 3.401(7) 137.5 3_666
O1 H1WA N2 0.840(19) 2.14(4) 2.920(6) 154(7) .
O1 H1WB F2 0.86(2) 2.12(3) 2.950(6) 164(6) 4_575
C1 H1B O1 0.97 2.56 3.436(7) 150.5 2_645
C5 H5A Br1 0.97 3.08 3.999(6) 158.6 4_565
C8 H8A F1 0.97 2.43 3.361(7) 159.7 4_565
C6 H6A F2 0.97 2.61 3.538(6) 159.2 4_575
C4 H4B F1 0.97 2.62 3.401(7) 137.5 3_666
O1 H1WA N2 0.840(19) 2.14(4) 2.920(6) 154(7) .
O1 H1WB F2 0.86(2) 2.12(3) 2.950(6) 164(6) 4_575
C1 H1B O1 0.97 2.56 3.436(7) 150.5 2_645
C5 H5A Br1 0.97 3.08 3.999(6) 158.6 4_565
C8 H8A F1 0.97 2.43 3.361(7) 159.7 4_565
C6 H6A F2 0.97 2.61 3.538(6) 159.2 4_575
C4 H4B F1 0.97 2.62 3.401(7) 137.5 3_666
C4 H4B F1 0.97 2.62 3.401(7) 137.5 3_666
C6 H6A F2 0.97 2.61 3.538(6) 159.2 4_575
C8 H8A F1 0.97 2.43 3.361(7) 159.7 4_565
C5 H5A Br1 0.97 3.08 3.999(6) 158.6 4_565
C1 H1B O1 0.97 2.56 3.436(7) 150.5 2_645
O1 H1WB F2 0.86(2) 2.12(3) 2.950(6) 164(6) 4_575
O1 H1WA N2 0.840(19) 2.14(4) 2.920(6) 154(7) .

_refine_diff_density_max         0.709
_refine_diff_density_min         -1.010
_refine_diff_density_rms         0.113

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1473189'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H16 Cl N2, Cl O4, H2 O'
_chemical_formula_sum            'C8 H18 Cl2 N2 O5'
_chemical_formula_weight         293.14

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

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

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

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

_cell_length_a                   10.919(2)
_cell_length_b                   10.331(2)
_cell_length_c                   11.330(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.06(3)
_cell_angle_gamma                90
_cell_volume                     1274.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8606
_cell_measurement_theta_min      3.187
_cell_measurement_theta_max      27.482

_exptl_crystal_description       blcok
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.521
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   NONE
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8606
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.187
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2932
_reflns_number_gt                2361
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+0.6795P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0122(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2922
_refine_ls_number_parameters     161
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.77298(5) 0.50038(5) 0.75410(5) 0.03651(16) Uani 1 1 d . . . . .
Cl2 Cl 0.98200(5) 0.24693(6) 0.50795(5) 0.04778(19) Uani 1 1 d . . . . .
N1 N 0.78464(14) 0.47440(16) 0.26997(14) 0.0286(4) Uani 1 1 d . . . . .
C7 C 0.88852(18) 0.4052(2) 0.33896(19) 0.0369(5) Uani 1 1 d . . . . .
H7A H 0.9299 0.3496 0.2854 0.044 Uiso 1 1 calc R U . . .
H7B H 0.9475 0.4689 0.3702 0.044 Uiso 1 1 calc R U . . .
N2 N 0.61651(15) 0.59743(17) 0.14573(16) 0.0357(4) Uani 1 1 d . . . . .
C3 C 0.6965(2) 0.3810(2) 0.2073(2) 0.0387(5) Uani 1 1 d . . . . .
H3A H 0.6578 0.3280 0.2647 0.046 Uiso 1 1 calc R U . . .
H3B H 0.7404 0.3244 0.1566 0.046 Uiso 1 1 calc R U . . .
C4 C 0.5984(2) 0.4575(2) 0.1327(2) 0.0426(5) Uani 1 1 d . . . . .
H4A H 0.6016 0.4340 0.0501 0.051 Uiso 1 1 calc R U . . .
H4B H 0.5178 0.4347 0.1570 0.051 Uiso 1 1 calc R U . . .
C6 C 0.7386(2) 0.6304(2) 0.1066(2) 0.0389(5) Uani 1 1 d . . . . .
H6A H 0.7518 0.7229 0.1147 0.047 Uiso 1 1 calc R U . . .
H6B H 0.7416 0.6083 0.0236 0.047 Uiso 1 1 calc R U . . .
C2 C 0.6134(2) 0.6317(2) 0.27130(19) 0.0399(5) Uani 1 1 d . . . . .
H2A H 0.5336 0.6097 0.2982 0.048 Uiso 1 1 calc R U . . .
H2B H 0.6248 0.7244 0.2805 0.048 Uiso 1 1 calc R U . . .
C8 C 0.84794(19) 0.3245(2) 0.43979(19) 0.0401(5) Uani 1 1 d . . . . .
H8A H 0.7886 0.2602 0.4106 0.048 Uiso 1 1 calc R U . . .
H8B H 0.8100 0.3789 0.4967 0.048 Uiso 1 1 calc R U . . .
C5 C 0.8405(2) 0.5586(2) 0.1785(2) 0.0453(6) Uani 1 1 d . . . . .
H5A H 0.8862 0.5053 0.1266 0.054 Uiso 1 1 calc R U . . .
H5B H 0.8968 0.6203 0.2176 0.054 Uiso 1 1 calc R U . . .
C1 C 0.7132(2) 0.5608(2) 0.34758(19) 0.0390(5) Uani 1 1 d . . . . .
H1A H 0.7680 0.6231 0.3878 0.047 Uiso 1 1 calc R U . . .
H1B H 0.6760 0.5092 0.4070 0.047 Uiso 1 1 calc R U . . .
O3 O 0.86274(16) 0.40603(18) 0.72736(17) 0.0570(5) Uani 1 1 d . . . . .
O1 O 0.69473(18) 0.4462(2) 0.83708(19) 0.0698(6) Uani 1 1 d . . . . .
O2 O 0.7010(2) 0.5322(2) 0.6481(2) 0.0788(7) Uani 1 1 d . . . . .
O4 O 0.8315(2) 0.61368(19) 0.80217(19) 0.0695(6) Uani 1 1 d . . . . .
O5 O 0.4792(2) 0.8207(2) 0.0469(2) 0.0756(6) Uani 1 1 d D . . . .
H5WB H 0.534(3) 0.876(2) 0.065(3) 0.091 Uiso 1 1 d D U . . .
H5WA H 0.501(3) 0.7482(19) 0.073(3) 0.091 Uiso 1 1 d D 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 O4 1.4234(19) . ?
Cl1 O2 1.426(2) . ?
Cl1 O1 1.4286(19) . ?
Cl1 O3 1.4298(17) . ?
Cl2 C8 1.795(2) . ?
N1 C3 1.505(3) . ?
N1 C1 1.509(3) . ?
N1 C7 1.511(3) . ?
N1 C5 1.514(3) . ?
C7 C8 1.506(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N2 C4 1.465(3) . ?
N2 C2 1.469(3) . ?
N2 C6 1.475(3) . ?
C3 C4 1.535(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C5 1.525(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C2 C1 1.529(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O5 H5WB 0.846(17) . ?
O5 H5WA 0.833(17) . ?

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
O4 Cl1 O2 109.78(14) . . ?
O4 Cl1 O1 110.10(13) . . ?
O2 Cl1 O1 108.96(15) . . ?
O4 Cl1 O3 110.22(12) . . ?
O2 Cl1 O3 108.90(13) . . ?
O1 Cl1 O3 108.86(12) . . ?
C3 N1 C1 108.33(16) . . ?
C3 N1 C7 111.87(16) . . ?
C1 N1 C7 112.25(16) . . ?
C3 N1 C5 108.71(17) . . ?
C1 N1 C5 108.00(17) . . ?
C7 N1 C5 107.56(15) . . ?
C8 C7 N1 113.83(16) . . ?
C8 C7 H7A 108.8 . . ?
N1 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
N1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C4 N2 C2 108.85(18) . . ?
C4 N2 C6 108.43(17) . . ?
C2 N2 C6 108.62(17) . . ?
N1 C3 C4 109.13(17) . . ?
N1 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
N1 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N2 C4 C3 111.63(17) . . ?
N2 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
N2 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
N2 C6 C5 111.60(17) . . ?
N2 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N2 C2 C1 111.56(17) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C7 C8 Cl2 107.38(14) . . ?
C7 C8 H8A 110.2 . . ?
Cl2 C8 H8A 110.2 . . ?
C7 C8 H8B 110.2 . . ?
Cl2 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
N1 C5 C6 109.33(16) . . ?
N1 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
N1 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
N1 C1 C2 109.35(17) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
H5WB O5 H5WA 111(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
C3 N1 C7 C8 -64.9(2) . . . . ?
C1 N1 C7 C8 57.1(2) . . . . ?
C5 N1 C7 C8 175.8(2) . . . . ?
C1 N1 C3 C4 59.4(2) . . . . ?
C7 N1 C3 C4 -176.33(17) . . . . ?
C5 N1 C3 C4 -57.7(2) . . . . ?
C2 N2 C4 C3 -58.1(2) . . . . ?
C6 N2 C4 C3 59.9(2) . . . . ?
N1 C3 C4 N2 -1.3(3) . . . . ?
C4 N2 C6 C5 -59.0(2) . . . . ?
C2 N2 C6 C5 59.1(2) . . . . ?
C4 N2 C2 C1 59.4(2) . . . . ?
C6 N2 C2 C1 -58.5(2) . . . . ?
N1 C7 C8 Cl2 178.42(15) . . . . ?
C3 N1 C5 C6 58.6(2) . . . . ?
C1 N1 C5 C6 -58.7(2) . . . . ?
C7 N1 C5 C6 179.95(19) . . . . ?
N2 C6 C5 N1 -0.2(3) . . . . ?
C3 N1 C1 C2 -58.3(2) . . . . ?
C7 N1 C1 C2 177.67(18) . . . . ?
C5 N1 C1 C2 59.3(2) . . . . ?
N2 C2 C1 N1 -0.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5WA N2 0.833(17) 2.13(2) 2.930(3) 160(3) .
O5 H5WB O2 0.846(17) 2.21(2) 3.017(3) 161(3) 4_575
C1 H1B O5 0.97 2.66 3.514(3) 147.4 2_645
C8 H8B O3 0.97 2.65 3.358(3) 130.1 .
C8 H8A O1 0.97 2.48 3.420(3) 162.2 4_565
C6 H6A O2 0.97 2.62 3.545(3) 158.8 4_575
C4 H4B O1 0.97 2.63 3.392(3) 135.5 3_666
C4 H4B O1 0.97 2.63 3.392(3) 135.5 3_666
C6 H6A O2 0.97 2.62 3.545(3) 158.8 4_575
C8 H8A O1 0.97 2.48 3.420(3) 162.2 4_565
C8 H8B O3 0.97 2.65 3.358(3) 130.1 .
C1 H1B O5 0.97 2.66 3.514(3) 147.4 2_645
O5 H5WB O2 0.846(17) 2.21(2) 3.017(3) 161(3) 4_575
O5 H5WA N2 0.833(17) 2.13(2) 2.930(3) 160(3) .

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.055

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 1473190'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H16 Br N2, Cl O4, D2 O'
_chemical_formula_sum            'C8 H16 Br Cl D2 N2 O5'
_chemical_formula_weight         339.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.018(2)
_cell_length_b                   10.388(2)
_cell_length_c                   11.406(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.03(3)
_cell_angle_gamma                90
_cell_volume                     1302.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13080
_cell_measurement_theta_min      3.165
_cell_measurement_theta_max      27.482

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    3.373
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13080
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.165
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2988
_reflns_number_gt                2358
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²+0.7872P] 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         2986
_refine_ls_number_parameters     160
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1094
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.044
_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 0.77133(8) 0.50332(7) 0.75461(7) 0.0407(2) Uani 1 1 d . . . . .
Br1 Br 0.98616(3) 0.24036(3) 0.51443(3) 0.04829(15) Uani 1 1 d . . . . .
N1 N 0.7791(2) 0.4735(2) 0.2717(2) 0.0325(5) Uani 1 1 d . . . . .
C7 C 0.8826(3) 0.4040(3) 0.3411(3) 0.0411(7) Uani 1 1 d . . . . .
H7A H 0.9238 0.3487 0.2880 0.049 Uiso 1 1 calc R U . . .
H7B H 0.9410 0.4673 0.3724 0.049 Uiso 1 1 calc R U . . .
N2 N 0.6136(2) 0.5954(2) 0.1475(2) 0.0390(6) Uani 1 1 d . . . . .
C3 C 0.6943(3) 0.3798(3) 0.2071(3) 0.0423(8) Uani 1 1 d . . . . .
H3A H 0.6567 0.3247 0.2628 0.051 Uiso 1 1 calc R U . . .
H3B H 0.7395 0.3260 0.1560 0.051 Uiso 1 1 calc R U . . .
C4 C 0.5959(3) 0.4557(3) 0.1338(3) 0.0473(8) Uani 1 1 d . . . . .
H4A H 0.5986 0.4329 0.0516 0.057 Uiso 1 1 calc R U . . .
H4B H 0.5163 0.4324 0.1584 0.057 Uiso 1 1 calc R U . . .
C6 C 0.7345(3) 0.6287(3) 0.1099(3) 0.0425(7) Uani 1 1 d . . . . .
H6A H 0.7466 0.7209 0.1168 0.051 Uiso 1 1 calc R U . . .
H6B H 0.7389 0.6054 0.0280 0.051 Uiso 1 1 calc R U . . .
C2 C 0.6086(3) 0.6285(3) 0.2718(3) 0.0433(8) Uani 1 1 d . . . . .
H2A H 0.5288 0.6071 0.2970 0.052 Uiso 1 1 calc R U . . .
H2B H 0.6202 0.7206 0.2816 0.052 Uiso 1 1 calc R U . . .
C8 C 0.8421(3) 0.3245(3) 0.4401(3) 0.0446(8) Uani 1 1 d . . . . .
H8A H 0.7834 0.2606 0.4108 0.053 Uiso 1 1 calc R U . . .
H8B H 0.8043 0.3786 0.4964 0.053 Uiso 1 1 calc R U . . .
C5 C 0.8352(3) 0.5595(3) 0.1837(3) 0.0457(8) Uani 1 1 d . . . . .
H5A H 0.8836 0.5084 0.1332 0.055 Uiso 1 1 calc R U . . .
H5B H 0.8883 0.6220 0.2244 0.055 Uiso 1 1 calc R U . . .
C1 C 0.7066(3) 0.5564(3) 0.3497(3) 0.0413(7) Uani 1 1 d . . . . .
H1A H 0.7598 0.6177 0.3921 0.050 Uiso 1 1 calc R U . . .
H1B H 0.6684 0.5033 0.4066 0.050 Uiso 1 1 calc R U . . .
O3 O 0.8636(2) 0.4129(3) 0.7296(3) 0.0690(8) Uani 1 1 d . . . . .
O1 O 0.6962(3) 0.4469(3) 0.8377(3) 0.0784(9) Uani 1 1 d . . . . .
O2 O 0.6989(3) 0.5306(3) 0.6494(3) 0.0822(9) Uani 1 1 d . . . . .
O4 O 0.8243(3) 0.6189(3) 0.8008(3) 0.0820(10) Uani 1 1 d . . . . .
O5 O 0.4818(3) 0.8189(3) 0.0477(3) 0.0778(9) Uani 1 1 d D . . . .
D5WB D 0.536(3) 0.872(3) 0.064(4) 0.093 Uiso 1 1 d D U . . .
D5WA D 0.502(4) 0.744(2) 0.070(5) 0.093 Uiso 1 1 d D 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 O4 1.421(3) . ?
Cl1 O2 1.422(3) . ?
Cl1 O1 1.428(3) . ?
Cl1 O3 1.428(3) . ?
Br1 C8 1.952(3) . ?
N1 C3 1.505(4) . ?
N1 C1 1.508(4) . ?
N1 C5 1.509(4) . ?
N1 C7 1.523(4) . ?
C7 C8 1.492(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N2 C2 1.463(4) . ?
N2 C6 1.469(4) . ?
N2 C4 1.471(4) . ?
C3 C4 1.540(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C5 1.525(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C2 C1 1.544(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O5 D5WB 0.831(18) . ?
O5 D5WA 0.848(18) . ?

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
O4 Cl1 O2 109.64(19) . . ?
O4 Cl1 O1 110.1(2) . . ?
O2 Cl1 O1 109.0(2) . . ?
O4 Cl1 O3 110.5(2) . . ?
O2 Cl1 O3 109.13(19) . . ?
O1 Cl1 O3 108.49(18) . . ?
C3 N1 C1 108.8(2) . . ?
C3 N1 C5 109.0(2) . . ?
C1 N1 C5 108.3(3) . . ?
C3 N1 C7 111.4(2) . . ?
C1 N1 C7 111.9(2) . . ?
C5 N1 C7 107.4(2) . . ?
C8 C7 N1 113.7(2) . . ?
C8 C7 H7A 108.8 . . ?
N1 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
N1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C2 N2 C6 108.9(2) . . ?
C2 N2 C4 108.7(3) . . ?
C6 N2 C4 108.5(3) . . ?
N1 C3 C4 108.9(3) . . ?
N1 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
N1 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N2 C4 C3 111.4(2) . . ?
N2 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N2 C6 C5 111.6(2) . . ?
N2 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N2 C2 C1 111.8(2) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C7 C8 Br1 107.4(2) . . ?
C7 C8 H8A 110.2 . . ?
Br1 C8 H8A 110.2 . . ?
C7 C8 H8B 110.2 . . ?
Br1 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
N1 C5 C6 109.2(2) . . ?
N1 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
N1 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
N1 C1 C2 108.4(2) . . ?
N1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
N1 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
D5WB O5 D5WA 112(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
C3 N1 C7 C8 -66.4(3) . . . . ?
C1 N1 C7 C8 55.7(4) . . . . ?
C5 N1 C7 C8 174.3(3) . . . . ?
C1 N1 C3 C4 59.1(3) . . . . ?
C5 N1 C3 C4 -58.7(3) . . . . ?
C7 N1 C3 C4 -177.1(2) . . . . ?
C2 N2 C4 C3 -59.3(3) . . . . ?
C6 N2 C4 C3 59.0(3) . . . . ?
N1 C3 C4 N2 0.3(4) . . . . ?
C2 N2 C6 C5 57.9(3) . . . . ?
C4 N2 C6 C5 -60.3(3) . . . . ?
C6 N2 C2 C1 -59.1(3) . . . . ?
C4 N2 C2 C1 58.9(3) . . . . ?
N1 C7 C8 Br1 178.4(2) . . . . ?
C3 N1 C5 C6 57.8(3) . . . . ?
C1 N1 C5 C6 -60.4(3) . . . . ?
C7 N1 C5 C6 178.6(3) . . . . ?
N2 C6 C5 N1 1.8(4) . . . . ?
C3 N1 C1 C2 -59.5(3) . . . . ?
C5 N1 C1 C2 58.8(3) . . . . ?
C7 N1 C1 C2 177.0(3) . . . . ?
N2 C2 C1 N1 0.5(4) . . . . ?

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_293K
_database_code_depnum_ccdc_archive 'CCDC 1473191'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H16 Br N2, Cl O4, H2 O'
_chemical_formula_sum            'C8 H18 Br Cl N2 O5'
_chemical_formula_weight         337.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.980(2)
_cell_length_b                   10.333(2)
_cell_length_c                   11.370(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.92(3)
_cell_angle_gamma                90
_cell_volume                     1287.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8773
_cell_measurement_theta_min      3.180
_cell_measurement_theta_max      27.469

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.413
_shelx_estimated_absorpt_T_min   0.239
_shelx_estimated_absorpt_T_max   0.239
_exptl_absorpt_correction_type   NONE
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8773
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.180
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2957
_reflns_number_gt                2422
_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       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²+0.7872P] 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         2951
_refine_ls_number_parameters     160
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.77141(7) 0.50302(7) 0.75481(7) 0.03812(19) Uani 1 1 d . . . . .
Br1 Br 0.98616(3) 0.24030(3) 0.51450(3) 0.04524(13) Uani 1 1 d . . . . .
N1 N 0.7796(2) 0.4737(2) 0.2719(2) 0.0293(5) Uani 1 1 d . . . . .
C7 C 0.8829(3) 0.4048(3) 0.3412(3) 0.0384(7) Uani 1 1 d . . . . .
H7A H 0.9247 0.3494 0.2880 0.046 Uiso 1 1 calc R U . . .
H7B H 0.9410 0.4687 0.3727 0.046 Uiso 1 1 calc R U . . .
N2 N 0.6131(2) 0.5955(2) 0.1474(2) 0.0359(6) Uani 1 1 d . . . . .
C3 C 0.6947(3) 0.3800(3) 0.2076(3) 0.0390(7) Uani 1 1 d . . . . .
H3A H 0.6571 0.3245 0.2636 0.047 Uiso 1 1 calc R U . . .
H3B H 0.7399 0.3258 0.1561 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5957(3) 0.4561(3) 0.1345(3) 0.0434(7) Uani 1 1 d . . . . .
H4A H 0.5980 0.4327 0.0520 0.052 Uiso 1 1 calc R U . . .
H4B H 0.5160 0.4327 0.1597 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7346(3) 0.6287(3) 0.1097(3) 0.0403(7) Uani 1 1 d . . . . .
H6A H 0.7466 0.7215 0.1163 0.048 Uiso 1 1 calc R U . . .
H6B H 0.7392 0.6051 0.0276 0.048 Uiso 1 1 calc R U . . .
C2 C 0.6086(3) 0.6292(3) 0.2724(3) 0.0397(7) Uani 1 1 d . . . . .
H2A H 0.5286 0.6080 0.2983 0.048 Uiso 1 1 calc R U . . .
H2B H 0.6207 0.7217 0.2821 0.048 Uiso 1 1 calc R U . . .
C8 C 0.8421(3) 0.3242(3) 0.4409(3) 0.0421(7) Uani 1 1 d . . . . .
H8A H 0.7833 0.2599 0.4115 0.051 Uiso 1 1 calc R U . . .
H8B H 0.8040 0.3784 0.4976 0.051 Uiso 1 1 calc R U . . .
C5 C 0.8358(3) 0.5599(3) 0.1836(3) 0.0429(7) Uani 1 1 d . . . . .
H5A H 0.8845 0.5085 0.1329 0.051 Uiso 1 1 calc R U . . .
H5B H 0.8888 0.6230 0.2242 0.051 Uiso 1 1 calc R U . . .
C1 C 0.7063(3) 0.5570(3) 0.3495(3) 0.0387(7) Uani 1 1 d . . . . .
H1A H 0.7595 0.6186 0.3921 0.046 Uiso 1 1 calc R U . . .
H1B H 0.6679 0.5036 0.4066 0.046 Uiso 1 1 calc R U . . .
O3 O 0.8638(2) 0.4124(3) 0.7301(2) 0.0640(7) Uani 1 1 d . . . . .
O1 O 0.6959(2) 0.4468(3) 0.8381(3) 0.0742(8) Uani 1 1 d . . . . .
O2 O 0.6988(3) 0.5304(3) 0.6495(2) 0.0773(9) Uani 1 1 d . . . . .
O4 O 0.8247(3) 0.6190(3) 0.8007(3) 0.0784(9) Uani 1 1 d . . . . .
O5 O 0.4817(3) 0.8189(3) 0.0476(3) 0.0735(8) Uani 1 1 d D . . . .
H5WB H 0.531(3) 0.875(3) 0.069(4) 0.088 Uiso 1 1 d D U . . .
H5WA H 0.500(4) 0.745(2) 0.072(4) 0.088 Uiso 1 1 d D 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 O4 1.417(3) . ?
Cl1 O2 1.420(3) . ?
Cl1 O3 1.423(2) . ?
Cl1 O1 1.424(3) . ?
Br1 C8 1.943(3) . ?
N1 C3 1.500(4) . ?
N1 C1 1.506(4) . ?
N1 C5 1.506(4) . ?
N1 C7 1.513(3) . ?
C7 C8 1.499(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N2 C4 1.459(4) . ?
N2 C2 1.469(4) . ?
N2 C6 1.470(4) . ?
C3 C4 1.539(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C5 1.522(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C2 C1 1.532(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O5 H5WB 0.821(18) . ?
O5 H5WA 0.837(18) . ?

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
O4 Cl1 O2 109.64(18) . . ?
O4 Cl1 O3 110.30(19) . . ?
O2 Cl1 O3 109.34(17) . . ?
O4 Cl1 O1 110.1(2) . . ?
O2 Cl1 O1 108.8(2) . . ?
O3 Cl1 O1 108.55(17) . . ?
C3 N1 C1 108.4(2) . . ?
C3 N1 C5 109.0(2) . . ?
C1 N1 C5 108.2(2) . . ?
C3 N1 C7 111.6(2) . . ?
C1 N1 C7 112.1(2) . . ?
C5 N1 C7 107.4(2) . . ?
C8 C7 N1 113.8(2) . . ?
C8 C7 H7A 108.8 . . ?
N1 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
N1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C4 N2 C2 108.6(2) . . ?
C4 N2 C6 108.5(2) . . ?
C2 N2 C6 108.5(2) . . ?
N1 C3 C4 109.0(2) . . ?
N1 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
N1 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N2 C4 C3 111.6(2) . . ?
N2 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
N2 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
N2 C6 C5 111.9(2) . . ?
N2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C2 C1 111.7(2) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C7 C8 Br1 107.3(2) . . ?
C7 C8 H8A 110.3 . . ?
Br1 C8 H8A 110.3 . . ?
C7 C8 H8B 110.3 . . ?
Br1 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
N1 C5 C6 109.1(2) . . ?
N1 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
N1 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
N1 C1 C2 108.9(2) . . ?
N1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
H5WB O5 H5WA 114(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
C3 N1 C7 C8 -66.0(3) . . . . ?
C1 N1 C7 C8 55.9(3) . . . . ?
C5 N1 C7 C8 174.6(3) . . . . ?
C1 N1 C3 C4 58.8(3) . . . . ?
C5 N1 C3 C4 -58.8(3) . . . . ?
C7 N1 C3 C4 -177.3(2) . . . . ?
C2 N2 C4 C3 -59.3(3) . . . . ?
C6 N2 C4 C3 58.4(3) . . . . ?
N1 C3 C4 N2 0.6(4) . . . . ?
C4 N2 C6 C5 -60.1(3) . . . . ?
C2 N2 C6 C5 57.7(3) . . . . ?
C4 N2 C2 C1 58.5(3) . . . . ?
C6 N2 C2 C1 -59.2(3) . . . . ?
N1 C7 C8 Br1 178.17(19) . . . . ?
C3 N1 C5 C6 57.5(3) . . . . ?
C1 N1 C5 C6 -60.2(3) . . . . ?
C7 N1 C5 C6 178.6(2) . . . . ?
N2 C6 C5 N1 1.8(4) . . . . ?
C3 N1 C1 C2 -59.5(3) . . . . ?
C5 N1 C1 C2 58.6(3) . . . . ?
C7 N1 C1 C2 176.8(2) . . . . ?
N2 C2 C1 N1 0.9(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
O5 H5WA N2 0.837(18) 2.12(3) 2.911(4) 158(4) .
O5 H5WB O2 0.821(18) 2.22(2) 3.013(4) 161(4) 4_575
C1 H1B O5 0.97 2.59 3.466(5) 149.7 2_645
C8 H8B O2 0.97 2.66 3.627(5) 178.8 .
C8 H8A O1 0.97 2.46 3.395(5) 161.0 4_565
C6 H6A O2 0.97 2.65 3.577(4) 160.2 4_575
C4 H4B O1 0.97 2.64 3.390(4) 134.3 3_666
O5 H5WA N2 0.837(18) 2.12(3) 2.911(4) 158(4) .
O5 H5WB O2 0.821(18) 2.22(2) 3.013(4) 161(4) 4_575
C1 H1B O5 0.97 2.59 3.466(5) 149.7 2_645
C8 H8B O2 0.97 2.66 3.627(5) 178.8 .
C8 H8A O1 0.97 2.46 3.395(5) 161.0 4_565
C6 H6A O2 0.97 2.65 3.577(4) 160.2 4_575
C4 H4B O1 0.97 2.64 3.390(4) 134.3 3_666

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_333K
_database_code_depnum_ccdc_archive 'CCDC 1473192'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H16 Br N2, Cl O4, H2 O'
_chemical_formula_sum            'C8 H18 Br Cl N2 O5'
_chemical_formula_weight         337.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.055(6)
_cell_length_b                   10.452(6)
_cell_length_c                   11.388(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.249(9)
_cell_angle_gamma                90
_cell_volume                     1312.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    333(2)
_cell_measurement_reflns_used    14041
_cell_measurement_theta_min      2.685
_cell_measurement_theta_max      27.556

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    3.348
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      333(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14041
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.685
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3029
_reflns_number_gt                2210
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²+0.7872P] 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         3014
_refine_ls_number_parameters     160
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.77128(9) 0.50420(9) 0.75359(8) 0.0462(2) Uani 1 1 d . . . . .
Br1 Br 0.98647(4) 0.24051(4) 0.51405(4) 0.05521(17) Uani 1 1 d . . . . .
N1 N 0.7787(2) 0.4731(3) 0.2718(2) 0.0356(6) Uani 1 1 d . . . . .
C7 C 0.8827(3) 0.4030(4) 0.3410(3) 0.0498(10) Uani 1 1 d . . . . .
H7A H 0.9233 0.3482 0.2875 0.060 Uiso 1 1 calc R U . . .
H7B H 0.9413 0.4655 0.3726 0.060 Uiso 1 1 calc R U . . .
N2 N 0.6139(3) 0.5948(3) 0.1468(3) 0.0425(7) Uani 1 1 d . . . . .
C3 C 0.6938(3) 0.3797(4) 0.2076(3) 0.0480(10) Uani 1 1 d . . . . .
H3A H 0.6560 0.3255 0.2635 0.058 Uiso 1 1 calc R U . . .
H3B H 0.7383 0.3256 0.1566 0.058 Uiso 1 1 calc R U . . .
C4 C 0.5963(4) 0.4564(4) 0.1340(4) 0.0521(10) Uani 1 1 d . . . . .
H4A H 0.5987 0.4334 0.0517 0.063 Uiso 1 1 calc R U . . .
H4B H 0.5168 0.4338 0.1584 0.063 Uiso 1 1 calc R U . . .
C6 C 0.7346(3) 0.6274(4) 0.1101(3) 0.0491(10) Uani 1 1 d . . . . .
H6A H 0.7467 0.7191 0.1168 0.059 Uiso 1 1 calc R U . . .
H6B H 0.7393 0.6039 0.0282 0.059 Uiso 1 1 calc R U . . .
C2 C 0.6088(3) 0.6276(4) 0.2720(3) 0.0490(10) Uani 1 1 d . . . . .
H2A H 0.5292 0.6063 0.2969 0.059 Uiso 1 1 calc R U . . .
H2B H 0.6206 0.7190 0.2822 0.059 Uiso 1 1 calc R U . . .
C8 C 0.8425(3) 0.3240(4) 0.4393(3) 0.0533(10) Uani 1 1 d . . . . .
H8A H 0.7841 0.2604 0.4095 0.064 Uiso 1 1 calc R U . . .
H8B H 0.8047 0.3775 0.4957 0.064 Uiso 1 1 calc R U . . .
C5 C 0.8351(3) 0.5585(4) 0.1852(4) 0.0515(10) Uani 1 1 d . . . . .
H5A H 0.8840 0.5081 0.1351 0.062 Uiso 1 1 calc R U . . .
H5B H 0.8874 0.6207 0.2269 0.062 Uiso 1 1 calc R U . . .
C1 C 0.7060(3) 0.5556(4) 0.3494(3) 0.0473(9) Uani 1 1 d . . . . .
H1A H 0.7590 0.6162 0.3923 0.057 Uiso 1 1 calc R U . . .
H1B H 0.6677 0.5027 0.4060 0.057 Uiso 1 1 calc R U . . .
O3 O 0.8629(3) 0.4141(3) 0.7285(3) 0.0825(10) Uani 1 1 d . . . . .
O1 O 0.6972(3) 0.4469(4) 0.8369(3) 0.0918(11) Uani 1 1 d . . . . .
O2 O 0.6984(4) 0.5319(4) 0.6497(3) 0.0965(12) Uani 1 1 d . . . . .
O4 O 0.8238(4) 0.6179(3) 0.8011(3) 0.0972(12) Uani 1 1 d . . . . .
O5 O 0.4812(3) 0.8166(4) 0.0473(4) 0.0891(11) Uani 1 1 d D . . . .
H5WB H 0.534(4) 0.873(3) 0.063(5) 0.107 Uiso 1 1 d D U . . .
H5WA H 0.506(4) 0.744(3) 0.076(5) 0.107 Uiso 1 1 d D 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 O2 1.411(3) . ?
Cl1 O4 1.413(3) . ?
Cl1 O3 1.428(3) . ?
Cl1 O1 1.430(3) . ?
Br1 C8 1.954(4) . ?
N1 C5 1.500(5) . ?
N1 C3 1.505(4) . ?
N1 C1 1.509(4) . ?
N1 C7 1.532(4) . ?
C7 C8 1.485(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N2 C4 1.465(5) . ?
N2 C6 1.468(5) . ?
N2 C2 1.471(4) . ?
C3 C4 1.541(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C5 1.530(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C2 C1 1.535(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O5 H5WB 0.837(19) . ?
O5 H5WA 0.862(19) . ?

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
O2 Cl1 O4 110.0(2) . . ?
O2 Cl1 O3 109.7(2) . . ?
O4 Cl1 O3 110.7(2) . . ?
O2 Cl1 O1 108.8(3) . . ?
O4 Cl1 O1 109.7(2) . . ?
O3 Cl1 O1 107.8(2) . . ?
C5 N1 C3 110.0(3) . . ?
C5 N1 C1 108.1(3) . . ?
C3 N1 C1 108.4(3) . . ?
C5 N1 C7 106.8(3) . . ?
C3 N1 C7 110.9(3) . . ?
C1 N1 C7 112.6(3) . . ?
C8 C7 N1 113.5(3) . . ?
C8 C7 H7A 108.9 . . ?
N1 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
N1 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C4 N2 C6 108.5(3) . . ?
C4 N2 C2 108.2(3) . . ?
C6 N2 C2 108.8(3) . . ?
N1 C3 C4 108.2(3) . . ?
N1 C3 H3A 110.1 . . ?
C4 C3 H3A 110.1 . . ?
N1 C3 H3B 110.1 . . ?
C4 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N2 C4 C3 112.1(3) . . ?
N2 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
N2 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N2 C6 C5 111.7(3) . . ?
N2 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N2 C2 C1 111.5(3) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C7 C8 Br1 107.3(3) . . ?
C7 C8 H8A 110.3 . . ?
Br1 C8 H8A 110.3 . . ?
C7 C8 H8B 110.3 . . ?
Br1 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
N1 C5 C6 109.1(3) . . ?
N1 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
N1 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
N1 C1 C2 108.9(3) . . ?
N1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
H5WB O5 H5WA 110(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
C5 N1 C7 C8 174.0(3) . . . . ?
C3 N1 C7 C8 -66.1(4) . . . . ?
C1 N1 C7 C8 55.6(4) . . . . ?
C5 N1 C3 C4 -58.6(4) . . . . ?
C1 N1 C3 C4 59.4(4) . . . . ?
C7 N1 C3 C4 -176.5(3) . . . . ?
C6 N2 C4 C3 58.5(4) . . . . ?
C2 N2 C4 C3 -59.4(4) . . . . ?
N1 C3 C4 N2 0.2(4) . . . . ?
C4 N2 C6 C5 -60.1(4) . . . . ?
C2 N2 C6 C5 57.5(4) . . . . ?
C4 N2 C2 C1 58.7(4) . . . . ?
C6 N2 C2 C1 -59.0(4) . . . . ?
N1 C7 C8 Br1 178.9(2) . . . . ?
C3 N1 C5 C6 57.4(4) . . . . ?
C1 N1 C5 C6 -60.8(4) . . . . ?
C7 N1 C5 C6 177.8(3) . . . . ?
N2 C6 C5 N1 2.3(5) . . . . ?
C5 N1 C1 C2 59.1(4) . . . . ?
C3 N1 C1 C2 -60.1(4) . . . . ?
C7 N1 C1 C2 176.8(3) . . . . ?
N2 C2 C1 N1 0.6(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
O5 H5WA N2 0.862(19) 2.09(3) 2.927(5) 164(5) .
O5 H5WB O2 0.837(19) 2.24(3) 3.036(5) 159(5) 4_575
C1 H1B O5 0.97 2.63 3.503(6) 150.1 2_645
C8 H8A O1 0.97 2.49 3.417(6) 160.7 4_565

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_343K
_database_code_depnum_ccdc_archive 'CCDC 1473193'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H16 Br N2, Cl O4, H2 O'
_chemical_formula_sum            'C8 H18 Br Cl N2 O5'
_chemical_formula_weight         337.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.067(2)
_cell_length_b                   10.483(2)
_cell_length_c                   11.404(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.32(3)
_cell_angle_gamma                90
_cell_volume                     1319.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    343(2)
_cell_measurement_reflns_used    4766
_cell_measurement_theta_min      3.146
_cell_measurement_theta_max      27.474

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.330
_shelx_estimated_absorpt_T_min   0.245
_shelx_estimated_absorpt_T_max   0.245
_exptl_absorpt_correction_type   NONE
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      343(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4766
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.146
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measured_fraction_theta_full 0.870
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_Laue_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_point_group_measured_fraction_full 0.870
_reflns_number_total             3022
_reflns_number_gt                1315
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)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_number_reflns         3022
_refine_ls_number_parameters     160
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.971
_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 0.77103(15) 0.50534(16) 0.75294(15) 0.0528(5) Uani 1 1 d . . . . .
Br1 Br 0.98685(6) 0.24085(7) 0.51375(5) 0.0623(3) Uani 1 1 d . . . . .
N1 N 0.7776(4) 0.4724(5) 0.2723(4) 0.0425(12) Uani 1 1 d . . . . .
C7 C 0.8824(5) 0.4013(6) 0.3419(5) 0.0533(16) Uani 1 1 d . . . . .
H7A H 0.9228 0.3468 0.2884 0.064 Uiso 1 1 calc R U . . .
H7B H 0.9410 0.4634 0.3739 0.064 Uiso 1 1 calc R U . . .
N2 N 0.6146(4) 0.5948(5) 0.1471(4) 0.0494(13) Uani 1 1 d . . . . .
C3 C 0.6933(5) 0.3802(6) 0.2082(5) 0.0531(17) Uani 1 1 d . . . . .
H3A H 0.6548 0.3267 0.2638 0.064 Uiso 1 1 calc R U . . .
H3B H 0.7379 0.3258 0.1578 0.064 Uiso 1 1 calc R U . . .
C4 C 0.5977(6) 0.4565(6) 0.1343(5) 0.0613(19) Uani 1 1 d . . . . .
H4A H 0.6011 0.4336 0.0522 0.074 Uiso 1 1 calc R U . . .
H4B H 0.5180 0.4339 0.1576 0.074 Uiso 1 1 calc R U . . .
C6 C 0.7350(5) 0.6262(6) 0.1108(5) 0.0538(16) Uani 1 1 d . . . . .
H6A H 0.7478 0.7175 0.1174 0.065 Uiso 1 1 calc R U . . .
H6B H 0.7398 0.6025 0.0290 0.065 Uiso 1 1 calc R U . . .
C2 C 0.6089(5) 0.6257(6) 0.2721(5) 0.0536(16) Uani 1 1 d . . . . .
H2A H 0.5297 0.6030 0.2966 0.064 Uiso 1 1 calc R U . . .
H2B H 0.6197 0.7169 0.2833 0.064 Uiso 1 1 calc R U . . .
C8 C 0.8421(6) 0.3231(7) 0.4387(5) 0.0661(19) Uani 1 1 d . . . . .
H8A H 0.7842 0.2594 0.4086 0.079 Uiso 1 1 calc R U . . .
H8B H 0.8038 0.3763 0.4949 0.079 Uiso 1 1 calc R U . . .
C5 C 0.8351(5) 0.5564(6) 0.1868(6) 0.0581(17) Uani 1 1 d . . . . .
H5A H 0.8838 0.5056 0.1371 0.070 Uiso 1 1 calc R U . . .
H5B H 0.8876 0.6180 0.2287 0.070 Uiso 1 1 calc R U . . .
C1 C 0.7074(5) 0.5538(6) 0.3490(5) 0.0545(17) Uani 1 1 d . . . . .
H1A H 0.7610 0.6143 0.3911 0.065 Uiso 1 1 calc R U . . .
H1B H 0.6700 0.5013 0.4063 0.065 Uiso 1 1 calc R U . . .
O3 O 0.8627(4) 0.4158(6) 0.7271(5) 0.0956(17) Uani 1 1 d . . . . .
O1 O 0.6979(5) 0.4477(6) 0.8366(5) 0.1061(19) Uani 1 1 d . . . . .
O2 O 0.6976(6) 0.5328(5) 0.6511(5) 0.111(2) Uani 1 1 d . . . . .
O4 O 0.8238(5) 0.6175(5) 0.8006(5) 0.105(2) Uani 1 1 d . . . . .
O5 O 0.4821(5) 0.8147(7) 0.0457(5) 0.0989(19) Uani 1 1 d D . . . .
H5WB H 0.532(6) 0.873(5) 0.068(7) 0.119 Uiso 1 1 d D U . . .
H5WA H 0.499(7) 0.747(4) 0.086(6) 0.119 Uiso 1 1 d D 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 O2 1.396(5) . ?
Cl1 O4 1.404(5) . ?
Cl1 O3 1.429(5) . ?
Cl1 O1 1.431(6) . ?
Br1 C8 1.959(6) . ?
N1 C1 1.483(7) . ?
N1 C5 1.492(7) . ?
N1 C3 1.495(7) . ?
N1 C7 1.547(7) . ?
C7 C8 1.470(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N2 C6 1.462(7) . ?
N2 C4 1.467(8) . ?
N2 C2 1.468(7) . ?
C3 C4 1.528(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C5 1.539(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C2 C1 1.544(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O5 H5WB 0.85(2) . ?
O5 H5WA 0.86(2) . ?

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
O2 Cl1 O4 110.4(3) . . ?
O2 Cl1 O3 110.0(4) . . ?
O4 Cl1 O3 110.5(4) . . ?
O2 Cl1 O1 108.6(4) . . ?
O4 Cl1 O1 109.6(4) . . ?
O3 Cl1 O1 107.8(4) . . ?
C1 N1 C5 108.3(5) . . ?
C1 N1 C3 109.0(5) . . ?
C5 N1 C3 110.1(4) . . ?
C1 N1 C7 112.3(4) . . ?
C5 N1 C7 106.2(4) . . ?
C3 N1 C7 110.8(4) . . ?
C8 C7 N1 113.3(5) . . ?
C8 C7 H7A 108.9 . . ?
N1 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
N1 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C6 N2 C4 107.9(5) . . ?
C6 N2 C2 109.4(4) . . ?
C4 N2 C2 107.5(5) . . ?
N1 C3 C4 108.2(5) . . ?
N1 C3 H3A 110.1 . . ?
C4 C3 H3A 110.1 . . ?
N1 C3 H3B 110.1 . . ?
C4 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N2 C4 C3 112.6(4) . . ?
N2 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
N2 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N2 C6 C5 111.5(5) . . ?
N2 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N2 C2 C1 111.3(5) . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C7 C8 Br1 106.8(4) . . ?
C7 C8 H8A 110.4 . . ?
Br1 C8 H8A 110.4 . . ?
C7 C8 H8B 110.4 . . ?
Br1 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
N1 C5 C6 108.9(5) . . ?
N1 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
N1 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
N1 C1 C2 108.9(4) . . ?
N1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
H5WB O5 H5WA 109(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
C1 N1 C7 C8 56.1(7) . . . . ?
C5 N1 C7 C8 174.3(6) . . . . ?
C3 N1 C7 C8 -66.1(7) . . . . ?
C1 N1 C3 C4 60.0(6) . . . . ?
C5 N1 C3 C4 -58.6(6) . . . . ?
C7 N1 C3 C4 -175.9(5) . . . . ?
C6 N2 C4 C3 59.0(6) . . . . ?
C2 N2 C4 C3 -58.8(7) . . . . ?
N1 C3 C4 N2 -0.3(7) . . . . ?
C4 N2 C6 C5 -59.9(6) . . . . ?
C2 N2 C6 C5 56.7(6) . . . . ?
C6 N2 C2 C1 -57.7(6) . . . . ?
C4 N2 C2 C1 59.1(6) . . . . ?
N1 C7 C8 Br1 179.4(4) . . . . ?
C1 N1 C5 C6 -61.4(6) . . . . ?
C3 N1 C5 C6 57.6(7) . . . . ?
C7 N1 C5 C6 177.7(5) . . . . ?
N2 C6 C5 N1 2.4(7) . . . . ?
C5 N1 C1 C2 60.4(6) . . . . ?
C3 N1 C1 C2 -59.4(6) . . . . ?
C7 N1 C1 C2 177.4(5) . . . . ?
N2 C2 C1 N1 -1.0(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
O5 H5WA N2 0.86(2) 2.13(4) 2.923(7) 154(8) .
O5 H5WB O2 0.85(2) 2.23(3) 3.042(8) 160(6) 4_575
C8 H8A O1 0.97 2.49 3.418(10) 160.9 4_565
O5 H5WA N2 0.86(2) 2.13(4) 2.923(7) 154(8) .
O5 H5WB O2 0.85(2) 2.23(3) 3.042(8) 160(6) 4_575
C8 H8A O1 0.97 2.49 3.418(10) 160.9 4_565
O5 H5WA N2 0.86(2) 2.13(4) 2.923(7) 154(8) .
O5 H5WB O2 0.85(2) 2.23(3) 3.042(8) 160(6) 4_575
C8 H8A O1 0.97 2.49 3.418(10) 160.9 4_565
O5 H5WA N2 0.86(2) 2.13(4) 2.923(7) 154(8) .
O5 H5WB O2 0.85(2) 2.23(3) 3.042(8) 160(6) 4_575
C8 H8A O1 0.97 2.49 3.418(10) 160.9 4_565
O5 H5WA N2 0.86(2) 2.13(4) 2.923(7) 154(8) .
O5 H5WB O2 0.85(2) 2.23(3) 3.042(8) 160(6) 4_575
C8 H8A O1 0.97 2.49 3.418(10) 160.9 4_565
C8 H8A O1 0.97 2.49 3.418(10) 160.9 4_565
O5 H5WB O2 0.85(2) 2.23(3) 3.042(8) 160(6) 4_575
O5 H5WA N2 0.86(2) 2.13(4) 2.923(7) 154(8) .
C8 H8A O1 0.97 2.49 3.418(10) 160.9 4_565
O5 H5WB O2 0.85(2) 2.23(3) 3.042(8) 160(6) 4_575
O5 H5WA N2 0.86(2) 2.13(4) 2.923(7) 154(8) .
C8 H8A O1 0.97 2.49 3.418(10) 160.9 4_565
O5 H5WB O2 0.85(2) 2.23(3) 3.042(8) 160(6) 4_575
O5 H5WA N2 0.86(2) 2.13(4) 2.923(7) 154(8) .
C8 H8A O1 0.97 2.49 3.418(10) 160.9 4_565
O5 H5WB O2 0.85(2) 2.23(3) 3.042(8) 160(6) 4_575
O5 H5WA N2 0.86(2) 2.13(4) 2.923(7) 154(8) .
C8 H8A O1 0.97 2.49 3.418(10) 160.9 4_565
O5 H5WB O2 0.85(2) 2.23(3) 3.042(8) 160(6) 4_575
O5 H5WA N2 0.86(2) 2.13(4) 2.923(7) 154(8) .
C8 H8A O1 0.97 2.49 3.418(10) 160.9 4_565
O5 H5WB O2 0.85(2) 2.23(3) 3.042(8) 160(6) 4_575
O5 H5WA N2 0.86(2) 2.13(4) 2.923(7) 154(8) .
C8 H8A O1 0.97 2.49 3.418(10) 160.9 4_565
O5 H5WB O2 0.85(2) 2.23(3) 3.042(8) 160(6) 4_575
O5 H5WA N2 0.86(2) 2.13(4) 2.923(7) 154(8) .

_refine_diff_density_max         0.347
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.077


# start Validation Reply Form
_vrf_PLAT029_343K                
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.870 Note  
RESPONSE: The quality of the crystal become deteriorated after the phase transition and the weak diffraction cause the alert.
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# end Validation Reply Form


#END CIF

