# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_RT_CL_1NIL
_database_code_depnum_ccdc_archive 'CCDC 1564273'
_audit_update_record             
;
2017-07-24 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C11 H7 N O2 Cl4, C3 H8 O'
_chemical_formula_sum            'C14 H15 Cl4 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         387.07

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2167(7)
_cell_length_b                   14.4067(10)
_cell_length_c                   13.1603(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.874(2)
_cell_angle_gamma                90
_cell_volume                     1747.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3717
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      25.96
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792

_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.94


_diffrn_ambient_temperature      296.(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            17047
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             4337
_reflns_number_gt                2761
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1120
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_number_reflns         4337
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+0.3756P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2014.11.0.1'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7940(2) 0.32269(16) 0.76010(17) 0.0453(5) Uani d . . . 1 . .
H H1A 0.8404 0.2894 0.7095 0.054 Uiso calc U . R 1 . .
C C2 0.7976(3) 0.29145(19) 0.85811(18) 0.0544(6) Uani d . . . 1 . .
H H2A 0.8454 0.2364 0.8743 0.065 Uiso calc U . R 1 . .
C C3 0.7305(3) 0.34155(19) 0.93243(18) 0.0559(6) Uani d . . . 1 . .
H H3A 0.7337 0.3212 0.9995 0.067 Uiso calc U . R 1 . .
C C4 0.6586(3) 0.4218(2) 0.90736(18) 0.0558(6) Uani d . . . 1 . .
H H4 0.6124 0.456 0.9573 0.067 Uiso calc U . R 1 . .
C C5 0.6550(3) 0.45157(18) 0.80855(17) 0.0500(6) Uani d . . . 1 . .
H H5 0.6058 0.5058 0.791 0.06 Uiso calc U . R 1 . .
C C6 0.7201(2) 0.43493(15) 0.63311(15) 0.0403(5) Uani d . . . 1 . .
C C7 0.8054(2) 0.50929(16) 0.60632(16) 0.0426(5) Uani d . . . 1 . .
C C8 0.8028(2) 0.54055(15) 0.50617(16) 0.0422(5) Uani d . . . 1 . .
C C9 0.7146(2) 0.49758(15) 0.43344(16) 0.0415(5) Uani d . . . 1 . .
C C10 0.6281(2) 0.42251(16) 0.46157(15) 0.0414(5) Uani d . . . 1 . .
C C11 0.6312(2) 0.39156(16) 0.56082(16) 0.0418(5) Uani d . . . 1 . .
C C12 0.6701(4) 0.7179(4) 0.1267(3) 0.142(2) Uani d . . . 1 . .
H H12A 0.5943 0.6816 0.1565 0.213 Uiso calc U . R 1 . .
H H12B 0.6481 0.7279 0.056 0.213 Uiso calc U . R 1 . .
H H12C 0.6773 0.7766 0.1609 0.213 Uiso calc U . R 1 . .
C C13 0.8114(4) 0.6670(2) 0.1372(2) 0.0805(10) Uani d . . . 1 . .
H H13 0.8871 0.7051 0.1065 0.097 Uiso calc U . R 1 . .
C C14 0.8155(7) 0.5736(3) 0.0897(3) 0.155(2) Uani d . . . 1 . .
H H14A 0.9077 0.5451 0.1039 0.233 Uiso calc U . R 1 . .
H H14B 0.8018 0.5794 0.0175 0.233 Uiso calc U . R 1 . .
H H14C 0.7395 0.5359 0.1168 0.233 Uiso calc U . R 1 . .
Cl Cl1 0.91678(8) 0.56202(5) 0.69554(5) 0.0634(2) Uani d . . . 1 . .
Cl Cl2 0.90673(7) 0.63417(4) 0.47093(5) 0.05564(18) Uani d . . . 1 . .
Cl Cl3 0.52269(7) 0.29938(5) 0.59508(4) 0.05754(19) Uani d . . . 1 . .
Cl Cl4 0.54227(8) 0.34497(4) 0.16799(4) 0.05791(19) Uani d . . . 1 . .
N N1 0.72307(19) 0.40176(13) 0.73705(12) 0.0396(4) Uani d . . . 1 . .
O O1 0.70391(19) 0.52238(12) 0.33534(11) 0.0537(4) Uani d . . . 1 . .
H H1 0.7558 0.5676 0.3252 0.08 Uiso calc U . R 1 . .
O O2 0.53652(18) 0.38137(12) 0.39414(11) 0.0529(4) Uani d . . . 1 . .
H H2 0.5646 0.3909 0.3362 0.079 Uiso calc U . R 1 . .
O O3 0.8483(3) 0.65390(14) 0.24162(13) 0.0740(6) Uani d . . . 1 . .
H H3 0.859 0.7046 0.2691 0.111 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.346(3) ?
C1 C2 . 1.366(3) ?
C1 H1A . 0.93 ?
C2 C3 . 1.371(3) ?
C2 H2A . 0.93 ?
C3 C4 . 1.370(4) ?
C3 H3A . 0.93 ?
C4 C5 . 1.369(3) ?
C4 H4 . 0.93 ?
C5 N1 . 1.346(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.378(3) ?
C6 C11 . 1.394(3) ?
C6 N1 . 1.449(3) ?
C7 C8 . 1.393(3) ?
C7 Cl1 . 1.724(2) ?
C8 C9 . 1.391(3) ?
C8 Cl2 . 1.722(2) ?
C9 O1 . 1.342(2) ?
C9 C10 . 1.397(3) ?
C10 O2 . 1.352(3) ?
C10 C11 . 1.380(3) ?
C11 Cl3 . 1.726(2) ?
C12 C13 . 1.499(5) ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
C13 O3 . 1.423(3) ?
C13 C14 . 1.485(5) ?
C13 H13 . 0.98 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
O1 H1 . 0.82 ?
O2 H2 . 0.82 ?
O3 H3 . 0.82 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 119.8(2) ?
N1 C1 H1A . . 120.1 ?
C2 C1 H1A . . 120.1 ?
C1 C2 C3 . . 119.7(2) ?
C1 C2 H2A . . 120.1 ?
C3 C2 H2A . . 120.1 ?
C4 C3 C2 . . 119.6(2) ?
C4 C3 H3A . . 120.2 ?
C2 C3 H3A . . 120.2 ?
C5 C4 C3 . . 119.8(2) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
N1 C5 C4 . . 119.5(2) ?
N1 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C7 C6 C11 . . 120.38(19) ?
C7 C6 N1 . . 119.68(19) ?
C11 C6 N1 . . 119.9(2) ?
C6 C7 C8 . . 119.4(2) ?
C6 C7 Cl1 . . 120.30(17) ?
C8 C7 Cl1 . . 120.25(18) ?
C9 C8 C7 . . 120.6(2) ?
C9 C8 Cl2 . . 118.99(17) ?
C7 C8 Cl2 . . 120.42(18) ?
O1 C9 C8 . . 125.2(2) ?
O1 C9 C10 . . 115.30(19) ?
C8 C9 C10 . . 119.46(19) ?
O2 C10 C11 . . 118.9(2) ?
O2 C10 C9 . . 121.23(19) ?
C11 C10 C9 . . 119.8(2) ?
C10 C11 C6 . . 120.3(2) ?
C10 C11 Cl3 . . 119.48(17) ?
C6 C11 Cl3 . . 120.22(17) ?
C13 C12 H12A . . 109.5 ?
C13 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C13 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O3 C13 C14 . . 106.2(3) ?
O3 C13 C12 . . 110.4(3) ?
C14 C13 C12 . . 115.6(4) ?
O3 C13 H13 . . 108.2 ?
C14 C13 H13 . . 108.2 ?
C12 C13 H13 . . 108.2 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C1 N1 C5 . . 121.58(19) ?
C1 N1 C6 . . 119.61(18) ?
C5 N1 C6 . . 118.80(18) ?
C9 O1 H1 . . 109.5 ?
C10 O2 H2 . . 109.5 ?
C13 O3 H3 . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . -0.8(4) ?
C1 C2 C3 C4 . . . . 0.9(4) ?
C2 C3 C4 C5 . . . . -0.3(4) ?
C3 C4 C5 N1 . . . . -0.4(4) ?
C11 C6 C7 C8 . . . . -0.3(3) ?
N1 C6 C7 C8 . . . . 179.63(19) ?
C11 C6 C7 Cl1 . . . . -179.30(17) ?
N1 C6 C7 Cl1 . . . . 0.7(3) ?
C6 C7 C8 C9 . . . . 0.2(3) ?
Cl1 C7 C8 C9 . . . . 179.17(17) ?
C6 C7 C8 Cl2 . . . . 179.23(17) ?
Cl1 C7 C8 Cl2 . . . . -1.8(3) ?
C7 C8 C9 O1 . . . . 179.8(2) ?
Cl2 C8 C9 O1 . . . . 0.8(3) ?
C7 C8 C9 C10 . . . . 0.1(3) ?
Cl2 C8 C9 C10 . . . . -178.99(17) ?
O1 C9 C10 O2 . . . . -2.6(3) ?
C8 C9 C10 O2 . . . . 177.2(2) ?
O1 C9 C10 C11 . . . . -180.0(2) ?
C8 C9 C10 C11 . . . . -0.2(3) ?
O2 C10 C11 C6 . . . . -177.4(2) ?
C9 C10 C11 C6 . . . . 0.1(3) ?
O2 C10 C11 Cl3 . . . . 2.0(3) ?
C9 C10 C11 Cl3 . . . . 179.45(17) ?
C7 C6 C11 C10 . . . . 0.2(3) ?
N1 C6 C11 C10 . . . . -179.76(19) ?
C7 C6 C11 Cl3 . . . . -179.17(17) ?
N1 C6 C11 Cl3 . . . . 0.9(3) ?
C2 C1 N1 C5 . . . . 0.1(3) ?
C2 C1 N1 C6 . . . . 179.7(2) ?
C4 C5 N1 C1 . . . . 0.6(4) ?
C4 C5 N1 C6 . . . . -179.1(2) ?
C7 C6 N1 C1 . . . . -104.9(3) ?
C11 C6 N1 C1 . . . . 75.1(3) ?
C7 C6 N1 C5 . . . . 74.8(3) ?
C11 C6 N1 C5 . . . . -105.3(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C13 H13 O2 2_655 0.98 2.63 3.419(4) 137.1 ?
C2 H2A O2 4_666 0.93 2.46 3.353(3) 161.7 ?
C5 H5 Cl4 3_666 0.93 2.61 3.465(3) 153.5 ?
C1 H1A Cl4 4_666 0.93 2.75 3.553(2) 145.7 ?
O3 H3 Cl4 2_655 0.82 2.36 3.158(2) 163.8 ?
O2 H2 Cl4 . 0.82 2.32 3.0232(16) 144.6 ?
O1 H1 O3 . 0.82 1.87 2.633(2) 153.4 ?
O1 H1 Cl2 . 0.82 2.54 3.0283(17) 119.4 ?

####################################################################### 
# 
# 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_RT_CL_2Re_1R
_database_code_depnum_ccdc_archive 'CCDC 1564275'
_audit_update_record             
;
2017-07-24 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C6 H1 Cl4  O2, C5 H6 N'
_chemical_formula_sum            'C11 H7 Cl4 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         326.98

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   17.155(18)
_cell_length_b                   8.049(5)
_cell_length_c                   18.643(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.815(9)
_cell_angle_gamma                90
_cell_volume                     2571.(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8696
_cell_measurement_theta_min      2.7959
_cell_measurement_theta_max      37.4748
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312

_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            24269
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         37.55
_diffrn_reflns_theta_full        37.55
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       31

_refine_special_details          
;
;

_reflns_number_total             6746
_reflns_number_gt                5330
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0846
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_number_reflns         6746
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+0.7095P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.534
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2014.11.0.1'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.43357(7) 0.38496(13) 0.41876(6) 0.02232(18) Uani d . . . 1 . .
H H1 0.4556 0.4406 0.3796 0.027 Uiso calc U . R 1 . .
C C2 0.44933(7) 0.21672(13) 0.42966(6) 0.0247(2) Uani d . . . 1 . .
H H2 0.4823 0.1583 0.3988 0.03 Uiso calc U . R 1 . .
C C3 0.41594(6) 0.13601(13) 0.48647(6) 0.02358(19) Uani d . . . 1 . .
H H3 0.4242 0.0205 0.494 0.028 Uiso calc U . R 1 . .
C C4 0.37011(7) 0.22655(14) 0.53224(6) 0.0259(2) Uani d . . . 1 . .
H H4 0.348 0.1746 0.5722 0.031 Uiso calc U . R 1 . .
C C5 0.35744(7) 0.39410(13) 0.51833(6) 0.02261(19) Uani d . . . 1 . .
H H5 0.3263 0.4565 0.5494 0.027 Uiso calc U . R 1 . .
C C6 0.30367(5) 0.82099(10) 0.38569(5) 0.01348(14) Uani d . . . 1 . .
C C7 0.22580(5) 0.86951(11) 0.36807(5) 0.01368(14) Uani d . . . 1 . .
C C8 0.20761(5) 0.95074(11) 0.30319(5) 0.01412(14) Uani d . . . 1 . .
C C9 0.26585(5) 0.98789(10) 0.25533(5) 0.01446(14) Uani d . . . 1 . .
C C10 0.34290(5) 0.94165(11) 0.27222(5) 0.01497(14) Uani d . . . 1 . .
C C11 0.36080(5) 0.85819(11) 0.33693(5) 0.01409(14) Uani d . . . 1 . .
Cl Cl1 0.11182(2) 1.00501(3) 0.28372(2) 0.02008(5) Uani d . . . 1 . .
Cl Cl2 0.24194(2) 1.09387(3) 0.17670(2) 0.01989(5) Uani d . . . 1 . .
Cl Cl3 0.41552(2) 0.99156(4) 0.21495(2) 0.02504(6) Uani d . . . 1 . .
Cl Cl4 0.45593(2) 0.80037(3) 0.35962(2) 0.01795(5) Uani d . . . 1 . .
N N1 0.38805(5) 0.47002(10) 0.46215(4) 0.01792(14) Uani d . . . 1 . .
H H1A 0.3782 0.5758 0.4538 0.022 Uiso calc U . R 1 . .
O O1 0.31878(4) 0.74431(8) 0.44859(4) 0.01745(12) Uani d . . . 1 . .
O O2 0.16818(4) 0.83790(9) 0.41330(4) 0.01855(13) Uani d . . . 1 . .
H H2A 0.1879 0.8068 0.4532 0.028 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.3398(15) ?
C1 C2 . 1.3939(16) ?
C1 H1 . 0.95 ?
C2 C3 . 1.3897(17) ?
C2 H2 . 0.95 ?
C3 C4 . 1.3939(18) ?
C3 H3 . 0.95 ?
C4 C5 . 1.3885(16) ?
C4 H4 . 0.95 ?
C5 N1 . 1.3417(14) ?
C5 H5 . 0.95 ?
C6 O1 . 1.3392(12) ?
C6 C11 . 1.4015(15) ?
C6 C7 . 1.4148(18) ?
C7 O2 . 1.3547(14) ?
C7 C8 . 1.3966(14) ?
C8 C9 . 1.4041(16) ?
C8 Cl1 . 1.7218(18) ?
C9 C10 . 1.3942(18) ?
C9 Cl2 . 1.7280(12) ?
C10 C11 . 1.4017(14) ?
C10 Cl3 . 1.7274(14) ?
C11 Cl4 . 1.7295(18) ?
N1 H1A . 0.88 ?
O2 H2A . 0.84 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 121.53(10) ?
N1 C1 H1 . . 119.2 ?
C2 C1 H1 . . 119.2 ?
C3 C2 C1 . . 118.76(10) ?
C3 C2 H2 . . 120.6 ?
C1 C2 H2 . . 120.6 ?
C2 C3 C4 . . 119.21(10) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C5 C4 C3 . . 118.77(10) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
N1 C5 C4 . . 121.63(10) ?
N1 C5 H5 . . 119.2 ?
C4 C5 H5 . . 119.2 ?
O1 C6 C11 . . 123.70(9) ?
O1 C6 C7 . . 118.07(8) ?
C11 C6 C7 . . 118.22(9) ?
O2 C7 C8 . . 119.22(9) ?
O2 C7 C6 . . 120.87(9) ?
C8 C7 C6 . . 119.91(8) ?
C7 C8 C9 . . 120.95(9) ?
C7 C8 Cl1 . . 118.15(7) ?
C9 C8 Cl1 . . 120.91(8) ?
C10 C9 C8 . . 119.74(9) ?
C10 C9 Cl2 . . 120.42(7) ?
C8 C9 Cl2 . . 119.83(8) ?
C9 C10 C11 . . 119.18(8) ?
C9 C10 Cl3 . . 120.19(8) ?
C11 C10 Cl3 . . 120.61(8) ?
C6 C11 C10 . . 122.00(9) ?
C6 C11 Cl4 . . 117.74(8) ?
C10 C11 Cl4 . . 120.25(7) ?
C1 N1 C5 . . 120.05(10) ?
C1 N1 H1A . . 120.0 ?
C5 N1 H1A . . 120.0 ?
C7 O2 H2A . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . 0.84(17) ?
C1 C2 C3 C4 . . . . -2.26(17) ?
C2 C3 C4 C5 . . . . 1.82(17) ?
C3 C4 C5 N1 . . . . 0.09(18) ?
O1 C6 C7 O2 . . . . -0.57(12) ?
C11 C6 C7 O2 . . . . -179.56(8) ?
O1 C6 C7 C8 . . . . 179.60(8) ?
C11 C6 C7 C8 . . . . 0.61(12) ?
O2 C7 C8 C9 . . . . 179.08(8) ?
C6 C7 C8 C9 . . . . -1.09(13) ?
O2 C7 C8 Cl1 . . . . -0.61(11) ?
C6 C7 C8 Cl1 . . . . 179.23(7) ?
C7 C8 C9 C10 . . . . 0.71(13) ?
Cl1 C8 C9 C10 . . . . -179.62(7) ?
C7 C8 C9 Cl2 . . . . -178.11(7) ?
Cl1 C8 C9 Cl2 . . . . 1.56(11) ?
C8 C9 C10 C11 . . . . 0.14(13) ?
Cl2 C9 C10 C11 . . . . 178.96(7) ?
C8 C9 C10 Cl3 . . . . -178.25(7) ?
Cl2 C9 C10 Cl3 . . . . 0.57(11) ?
O1 C6 C11 C10 . . . . -178.69(8) ?
C7 C6 C11 C10 . . . . 0.24(13) ?
O1 C6 C11 Cl4 . . . . 0.32(12) ?
C7 C6 C11 Cl4 . . . . 179.25(6) ?
C9 C10 C11 C6 . . . . -0.62(13) ?
Cl3 C10 C11 C6 . . . . 177.76(7) ?
C9 C10 C11 Cl4 . . . . -179.60(7) ?
Cl3 C10 C11 Cl4 . . . . -1.22(11) ?
C2 C1 N1 C5 . . . . 1.07(16) ?
C4 C5 N1 C1 . . . . -1.54(16) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1 Cl3 4_545 0.95 2.92 3.780(2) 150.5 ?
C1 H1 Cl4 . 0.95 2.92 3.547(2) 124.7 ?
C5 H5 Cl2 8_565 0.95 2.87 3.637(2) 138.6 ?
N1 H1A Cl4 . 0.88 2.89 3.5070(16) 128.5 ?
N1 H1A O1 . 0.88 1.70 2.5142(16) 153.2 ?
O2 H2A O1 . 0.84 2.31 2.740(3) 112.4 ?
O2 H2A O1 2_556 0.84 1.91 2.6814(17) 152.7 ?

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1564274'
_audit_update_record             
;
2017-10-24 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_date             2017-10-22T17:55:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C11 H7 Br3 N O2,Br, C2H6O'
_chemical_formula_sum            'C13 H13 Br4 N O3'
_chemical_formula_weight         550.88

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.353(5)
_cell_length_b                   14.954(8)
_cell_length_c                   13.404(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.134(14)
_cell_angle_gamma                90
_cell_volume                     1667.6(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9708
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      29.01
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       shard
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    2.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    9.66
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.11
_exptl_absorpt_correction_T_max  0.45

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100.(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            17057
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.045
_diffrn_reflns_theta_max         29.038
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_reflns_Friedel_coverage         0
_reflns_number_total             4355
_reflns_number_gt                3883
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v2014.11.0.1'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0195P)²+4.3780P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4355
_refine_ls_number_parameters     248
_refine_ls_number_restraints     70
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.028
_refine_ls_R_factor_gt           0.022
_refine_ls_wR_factor_ref         0.0513
_refine_ls_wR_factor_gt          0.0486
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.918
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         1.078
_refine_diff_density_min         -0.997
_refine_diff_density_rms         0.096

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.53370(4) 0.41915(2) 0.29087(2) 0.01889(7) Uani 0.9644(8) 1 d D . P A 1
Br2 Br 0.59079(3) 0.33865(2) 0.52083(2) 0.01346(6) Uani 0.9644(8) 1 d D . P A 1
Br3 Br 0.94117(3) 0.71146(2) 0.40731(2) 0.01560(6) Uani 0.9644(8) 1 d D . P A 1
Br4 Br 0.91269(5) 0.64116(2) 0.83738(2) 0.01978(7) Uani 0.9644(8) 1 d . . P A 1
C1 C 0.8141(3) 0.54004(17) 0.19587(18) 0.0155(5) Uani 0.9644(8) 1 d D . P A 1
H1 H 0.874135 0.488154 0.216076 0.019 Uiso 0.9644(8) 1 calc R U P A 1
C2 C 0.8041(3) 0.56755(19) 0.09835(18) 0.0176(5) Uani 0.9644(8) 1 d D . P A 1
H2 H 0.855186 0.534388 0.049737 0.021 Uiso 0.9644(8) 1 calc R U P A 1
C3 C 0.7190(3) 0.64397(19) 0.07138(19) 0.0175(5) Uani 0.9644(8) 1 d D . P A 1
H3 H 0.711364 0.663683 0.003753 0.021 Uiso 0.9644(8) 1 calc R U P A 1
C4 C 0.6443(3) 0.69238(18) 0.14244(19) 0.0178(5) Uani 0.9644(8) 1 d D . P A 1
H4 H 0.586991 0.745643 0.124161 0.021 Uiso 0.9644(8) 1 calc R U P A 1
C5 C 0.6543(3) 0.66246(16) 0.23853(18) 0.0145(5) Uani 0.9644(8) 1 d D . P A 1
H5 H 0.602671 0.694308 0.287951 0.017 Uiso 0.9644(8) 1 calc R U P A 1
C6 C 0.7482(3) 0.55569(15) 0.36441(16) 0.0108(4) Uani 0.9644(8) 1 d D . P A 1
C7 C 0.6697(3) 0.47782(15) 0.38833(17) 0.0113(4) Uani 0.9644(8) 1 d D . P A 1
C8 C 0.6884(3) 0.44619(15) 0.48556(17) 0.0112(4) Uani 0.9644(8) 1 d D . P A 1
C9 C 0.7822(3) 0.49211(15) 0.55889(16) 0.0107(4) Uani 0.9644(8) 1 d D . P A 1
C10 C 0.8539(3) 0.57341(15) 0.53469(16) 0.0112(4) Uani 0.9644(8) 1 d D . P A 1
C11 C 0.8384(3) 0.60406(15) 0.43764(17) 0.0109(4) Uani 0.9644(8) 1 d D . P A 1
C12 C 0.7834(4) 0.3895(2) 0.9118(2) 0.0289(6) Uani 1 1 d . . . . .
H12A H 0.81451 0.445025 0.879833 0.043 Uiso 1 1 calc R U . . .
H12B H 0.849249 0.381541 0.975433 0.043 Uiso 1 1 calc R U . . .
H12C H 0.669732 0.392668 0.924367 0.043 Uiso 1 1 calc R U . . .
C13 C 0.8088(4) 0.31222(18) 0.84440(19) 0.0245(6) Uani 1 1 d . . . . .
H13A H 0.924495 0.305799 0.835235 0.029 Uiso 1 1 calc R U . . .
H13B H 0.771237 0.25626 0.874153 0.029 Uiso 1 1 calc R U . . .
N1 N 0.7379(2) 0.58727(13) 0.26335(14) 0.0107(4) Uani 0.9644(8) 1 d D . P A 1
O1 O 0.8146(2) 0.46700(11) 0.65331(12) 0.0146(3) Uani 0.9644(8) 1 d D . P A 1
H1A H 0.762602 0.420428 0.663989 0.022 Uiso 0.9644(8) 1 calc R U P A 1
O2 O 0.9433(2) 0.62017(12) 0.60451(12) 0.0147(3) Uani 0.9644(8) 1 d D . P A 1
H2A H 0.920552 0.604383 0.6617 0.022 Uiso 0.9644(8) 1 calc DR U P A 1
O3 O 0.7201(2) 0.32858(12) 0.75038(13) 0.0204(4) Uani 1 1 d . . . . .
H3B H 0.704247 0.280032 0.719546 0.031 Uiso 1 1 calc R U . . .
Br1A Br 0.9017(9) 0.6706(6) 0.4159(5) 0.0165(16) Uiso 0.0356(8) 1 d D U P A 2
C6A C 0.7035(10) 0.5247(8) 0.3515(10) 0.0156(19) Uiso 0.0356(8) 1 d DG U P A 2
C7A C 0.793(4) 0.5631(14) 0.4329(12) 0.0157(18) Uiso 0.0356(8) 1 d DG U P A 2
C8A C 0.794(5) 0.5244(19) 0.5272(11) 0.0157(18) Uiso 0.0356(8) 1 d DG U P A 2
C9A C 0.706(5) 0.4472(19) 0.5402(11) 0.0156(19) Uiso 0.0356(8) 1 d DG U P A 2
C10A C 0.616(5) 0.4087(19) 0.4589(14) 0.0155(19) Uiso 0.0356(8) 1 d DG U P A 2
C11A C 0.615(3) 0.4475(15) 0.3646(12) 0.0158(18) Uiso 0.0356(8) 1 d DG U P A 2
N1A N 0.7087(10) 0.5639(9) 0.2559(13) 0.015(2) Uiso 0.0356(8) 1 d DG U P A 2
C1A C 0.632(3) 0.6453(12) 0.2369(16) 0.015(2) Uiso 0.0356(8) 1 d DG U P A 2
H1AA H 0.577192 0.673428 0.287707 0.018 Uiso 0.0356(8) 1 calc R U P A 2
C2A C 0.635(4) 0.6857(14) 0.1437(18) 0.015(2) Uiso 0.0356(8) 1 d DG U P A 2
H2AA H 0.581957 0.74135 0.130735 0.018 Uiso 0.0356(8) 1 calc R U P A 2
C3A C 0.714(3) 0.6446(18) 0.0694(15) 0.015(2) Uiso 0.0356(8) 1 d DG U P A 2
H3A H 0.716255 0.672151 0.005685 0.018 Uiso 0.0356(8) 1 calc R U P A 2
C4A C 0.791(2) 0.5631(19) 0.0884(14) 0.015(2) Uiso 0.0356(8) 1 d DG U P A 2
H4A H 0.845789 0.535029 0.037604 0.018 Uiso 0.0356(8) 1 calc R U P A 2
C5A C 0.7884(18) 0.5228(13) 0.1816(14) 0.015(2) Uiso 0.0356(8) 1 d DG U P A 2
H5A H 0.841025 0.467105 0.194575 0.018 Uiso 0.0356(8) 1 calc R U P A 2
Br2A Br 0.8888(9) 0.5817(5) 0.6397(5) 0.0161(16) Uiso 0.0356(8) 1 d D U P A 2
Br3A Br 0.4780(10) 0.3981(5) 0.2613(6) 0.0184(17) Uiso 0.0356(8) 1 d D U P A 2
Br4A Br 0.9683(10) 0.6526(5) 0.8664(7) 0.0139(18) Uiso 0.0356(8) 1 d . . P A 2
O1A O 0.688(5) 0.404(3) 0.6255(19) 0.016(3) Uiso 0.0356(8) 1 d D U P A 2
H1AB H 0.591455 0.389998 0.627732 0.024 Uiso 0.0356(8) 1 calc R U P A 2
O2A O 0.522(5) 0.336(2) 0.470(3) 0.015(2) Uiso 0.0356(8) 1 d D U P A 2
H2AB H 0.43(3) 0.354(6) 0.49(5) 0.015(2) Uiso 0.0356(8) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C7 1.871(2) . ?
Br2 C8 1.882(2) . ?
Br3 C11 1.883(2) . ?
C1 N1 1.351(3) . ?
C1 C2 1.366(3) . ?
C1 H1 0.95 . ?
C2 C3 1.377(4) . ?
C2 H2 0.95 . ?
C3 C4 1.388(3) . ?
C3 H3 0.95 . ?
C4 C5 1.359(3) . ?
C4 H4 0.95 . ?
C5 N1 1.349(3) . ?
C5 H5 0.95 . ?
C6 C11 1.387(3) . ?
C6 C7 1.388(3) . ?
C6 N1 1.430(3) . ?
C7 C8 1.382(3) . ?
C8 C9 1.383(3) . ?
C9 O1 1.325(3) . ?
C9 C10 1.406(3) . ?
C10 O2 1.341(3) . ?
C10 C11 1.374(3) . ?
C12 C13 1.494(4) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 O3 1.425(3) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
O1 H1A 0.84 . ?
O2 H2A 0.84 . ?
O3 H3B 0.84 . ?
Br1A C7A 1.869(12) . ?
C6A C7A 1.39 . ?
C6A C11A 1.39 . ?
C6A N1A 1.414(14) . ?
C7A C8A 1.39 . ?
C8A C9A 1.39 . ?
C8A Br2A 1.850(12) . ?
C9A O1A 1.329(17) . ?
C9A C10A 1.39 . ?
C10A O2A 1.355(17) . ?
C10A C11A 1.39 . ?
C11A Br3A 1.867(11) . ?
N1A C1A 1.39 . ?
N1A C5A 1.39 . ?
C1A C2A 1.39 . ?
C1A H1AA 0.95 . ?
C2A C3A 1.39 . ?
C2A H2AA 0.95 . ?
C3A C4A 1.39 . ?
C3A H3A 0.95 . ?
C4A C5A 1.39 . ?
C4A H4A 0.95 . ?
C5A H5A 0.95 . ?
O1A H1AB 0.84 . ?
O2A H2AB 0.84(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
N1 C1 C2 119.4(2) . . ?
N1 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C1 C2 C3 119.2(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 119.6(2) . . ?
N1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C11 C6 C7 120.8(2) . . ?
C11 C6 N1 118.8(2) . . ?
C7 C6 N1 120.4(2) . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 Br1 120.55(17) . . ?
C6 C7 Br1 120.12(17) . . ?
C7 C8 C9 120.6(2) . . ?
C7 C8 Br2 120.94(17) . . ?
C9 C8 Br2 118.44(17) . . ?
O1 C9 C8 126.3(2) . . ?
O1 C9 C10 114.3(2) . . ?
C8 C9 C10 119.4(2) . . ?
O2 C10 C11 119.1(2) . . ?
O2 C10 C9 120.8(2) . . ?
C11 C10 C9 120.0(2) . . ?
C10 C11 C6 119.7(2) . . ?
C10 C11 Br3 118.86(17) . . ?
C6 C11 Br3 121.44(17) . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 C12 108.1(2) . . ?
O3 C13 H13A 110.1 . . ?
C12 C13 H13A 110.1 . . ?
O3 C13 H13B 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C5 N1 C1 122.3(2) . . ?
C5 N1 C6 119.65(19) . . ?
C1 N1 C6 118.0(2) . . ?
C9 O1 H1A 109.5 . . ?
C10 O2 H2A 109.5 . . ?
C13 O3 H3B 109.5 . . ?
C7A C6A C11A 120 . . ?
C7A C6A N1A 118.8(7) . . ?
C11A C6A N1A 121.2(7) . . ?
C8A C7A C6A 120 . . ?
C8A C7A Br1A 120.3(8) . . ?
C6A C7A Br1A 119.6(8) . . ?
C9A C8A C7A 120 . . ?
C9A C8A Br2A 118.4(10) . . ?
C7A C8A Br2A 121.1(10) . . ?
O1A C9A C8A 127.4(17) . . ?
O1A C9A C10A 112.6(17) . . ?
C8A C9A C10A 120 . . ?
O2A C10A C11A 118.4(17) . . ?
O2A C10A C9A 121.5(17) . . ?
C11A C10A C9A 120 . . ?
C10A C11A C6A 120 . . ?
C10A C11A Br3A 117.6(7) . . ?
C6A C11A Br3A 122.2(7) . . ?
C1A N1A C5A 120 . . ?
C1A N1A C6A 118.6(9) . . ?
C5A N1A C6A 121.4(9) . . ?
N1A C1A C2A 120 . . ?
N1A C1A H1AA 120 . . ?
C2A C1A H1AA 120 . . ?
C3A C2A C1A 120 . . ?
C3A C2A H2AA 120 . . ?
C1A C2A H2AA 120 . . ?
C2A C3A C4A 120 . . ?
C2A C3A H3A 120 . . ?
C4A C3A H3A 120 . . ?
C3A C4A C5A 120 . . ?
C3A C4A H4A 120 . . ?
C5A C4A H4A 120 . . ?
C4A C5A N1A 120 . . ?
C4A C5A H5A 120 . . ?
N1A C5A H5A 120 . . ?
C9A O1A H1AB 109.5 . . ?
C10A O2A H2AB 108(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
N1 C1 C2 C3 1.3(4) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 N1 0.8(4) . . . . ?
C11 C6 C7 C8 -3.1(3) . . . . ?
N1 C6 C7 C8 176.6(2) . . . . ?
C11 C6 C7 Br1 174.49(17) . . . . ?
N1 C6 C7 Br1 -5.8(3) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
Br1 C7 C8 C9 -176.58(17) . . . . ?
C6 C7 C8 Br2 -177.73(17) . . . . ?
Br1 C7 C8 Br2 4.7(3) . . . . ?
C7 C8 C9 O1 -177.1(2) . . . . ?
Br2 C8 C9 O1 1.6(3) . . . . ?
C7 C8 C9 C10 2.4(3) . . . . ?
Br2 C8 C9 C10 -178.84(17) . . . . ?
O1 C9 C10 O2 -1.5(3) . . . . ?
C8 C9 C10 O2 178.9(2) . . . . ?
O1 C9 C10 C11 175.8(2) . . . . ?
C8 C9 C10 C11 -3.8(3) . . . . ?
O2 C10 C11 C6 179.1(2) . . . . ?
C9 C10 C11 C6 1.8(3) . . . . ?
O2 C10 C11 Br3 -0.9(3) . . . . ?
C9 C10 C11 Br3 -178.20(17) . . . . ?
C7 C6 C11 C10 1.7(3) . . . . ?
N1 C6 C11 C10 -178.0(2) . . . . ?
C7 C6 C11 Br3 -178.34(17) . . . . ?
N1 C6 C11 Br3 2.0(3) . . . . ?
C4 C5 N1 C1 0.4(4) . . . . ?
C4 C5 N1 C6 -179.9(2) . . . . ?
C2 C1 N1 C5 -1.5(4) . . . . ?
C2 C1 N1 C6 178.8(2) . . . . ?
C11 C6 N1 C5 -69.9(3) . . . . ?
C7 C6 N1 C5 110.4(3) . . . . ?
C11 C6 N1 C1 109.8(3) . . . . ?
C7 C6 N1 C1 -69.9(3) . . . . ?
C11A C6A C7A C8A 0 . . . . ?
N1A C6A C7A C8A -178.0(15) . . . . ?
C11A C6A C7A Br1A -176(3) . . . . ?
N1A C6A C7A Br1A 6(3) . . . . ?
C6A C7A C8A C9A 0 . . . . ?
Br1A C7A C8A C9A 176(3) . . . . ?
C6A C7A C8A Br2A -172(3) . . . . ?
Br1A C7A C8A Br2A 5(2) . . . . ?
C7A C8A C9A O1A -177(4) . . . . ?
Br2A C8A C9A O1A -5(4) . . . . ?
C7A C8A C9A C10A 0 . . . . ?
Br2A C8A C9A C10A 172(3) . . . . ?
O1A C9A C10A O2A 1(5) . . . . ?
C8A C9A C10A O2A -176(5) . . . . ?
O1A C9A C10A C11A 177(4) . . . . ?
C8A C9A C10A C11A 0 . . . . ?
O2A C10A C11A C6A 176(4) . . . . ?
C9A C10A C11A C6A 0 . . . . ?
O2A C10A C11A Br3A 2(3) . . . . ?
C9A C10A C11A Br3A -175(3) . . . . ?
C7A C6A C11A C10A 0 . . . . ?
N1A C6A C11A C10A 178.0(15) . . . . ?
C7A C6A C11A Br3A 174(3) . . . . ?
N1A C6A C11A Br3A -8(3) . . . . ?
C7A C6A N1A C1A -72(2) . . . . ?
C11A C6A N1A C1A 110(2) . . . . ?
C7A C6A N1A C5A 108(2) . . . . ?
C11A C6A N1A C5A -70(2) . . . . ?
C5A N1A C1A C2A 0 . . . . ?
C6A N1A C1A C2A 180 . . . . ?
N1A C1A C2A C3A 0 . . . . ?
C1A C2A C3A C4A 0 . . . . ?
C2A C3A C4A C5A 0 . . . . ?
C3A C4A C5A N1A 0 . . . . ?
C1A N1A C5A C4A 0 . . . . ?
C6A N1A C5A C4A 180 . . . . ?

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
C1 H1 Br4 0.95 2.77 3.596(3) 146.4 3_766
C4 H4 Br3 0.95 3.12 3.731(3) 124 4_575
C4 H4 O2 0.95 2.34 3.284(3) 171.5 4_575
C5 H5 Br4 0.95 3.03 3.864(3) 146.9 4_575
C12 H12A Br4 0.98 3.11 4.064(4) 164.4 .
C12 H12B Br4 0.98 3.08 4.054(3) 173.9 3_767
O1 H1A Br2 0.84 2.6 3.121(2) 121.6 .
O1 H1A O3 0.84 1.85 2.605(3) 148.5 .
O2 H2A Br4 0.84 2.42 3.170(2) 148.3 .
O2 H2A O1 0.84 2.24 2.637(3) 109.5 .
O3 H3B Br4 0.84 2.39 3.199(2) 161.7 2_646



# END of CIF
