# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

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

data_lb-slq-7044
_database_code_depnum_ccdc_archive 'CCDC 1436892'
_audit_update_record             
;
2015-11-13 deposited with the CCDC.
2015-12-22 downloaded from the CCDC.
;
_audit_creation_date             2015-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 Cl2 N O4'
_chemical_formula_sum            'C16 H17 Cl2 N O4'
_chemical_formula_weight         358.20
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.3061(2)
_cell_length_b                   9.7010(2)
_cell_length_c                   20.7173(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1669.35(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4443
_cell_measurement_temperature    294.39(10)
_cell_measurement_theta_max      72.4770
_cell_measurement_theta_min      4.2650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8970
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.268
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.39(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.001
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   75.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  -30.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00  104.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   75.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000   60.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega  -31.00   53.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega   10.00  104.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega   91.00  176.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   91.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00  109.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00  109.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   91.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega  100.00  178.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
 12 omega   81.00  176.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
 13 omega  -31.00   53.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
 14 omega   20.00  104.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
 15 omega   20.00  104.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
 16 omega   20.00  104.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000 -180.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1707009000
_diffrn_orient_matrix_UB_12      -0.0079404000
_diffrn_orient_matrix_UB_13      0.0287654000
_diffrn_orient_matrix_UB_21      0.0675487000
_diffrn_orient_matrix_UB_22      -0.0395697000
_diffrn_orient_matrix_UB_23      -0.0667104000
_diffrn_orient_matrix_UB_31      0.0263177000
_diffrn_orient_matrix_UB_32      0.1536637000
_diffrn_orient_matrix_UB_33      -0.0157450000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2749
_reflns_number_total             2975
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1055 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2975
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1329
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00D), C00H(H00E,H00F), C00I(H00H,H00I), C00L(H00J,H00L)
2.c Aromatic/amide H refined with riding coordinates:
 N004(H004), C00C(H00C), C00G(H00G), C00K(H00K), C00M(H00M)
2.d Idealised Me refined as rotating group:
 C00N(H00N,H00O,H00P)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cl01 Cl 0.14441(14) 0.34294(11) 0.86487(6) 0.0662(3) Uani 1 1 d . . . . .
Cl02 Cl 0.0646(2) 0.89106(13) 0.89151(7) 0.0839(4) Uani 1 1 d . . . . .
O003 O 0.5448(4) 0.4682(2) 0.76091(13) 0.0530(7) Uani 1 1 d . . . . .
N004 N 0.4981(3) 0.6731(3) 0.71350(13) 0.0385(6) Uani 1 1 d . . . . .
H004 H 0.5191 0.7599 0.7139 0.046 Uiso 1 1 calc R . . . .
O005 O 0.1059(4) 0.6019(4) 0.93833(14) 0.0636(8) Uani 1 1 d . . . . .
O006 O 0.5720(4) 0.5725(3) 0.57859(15) 0.0676(8) Uani 1 1 d . . . . .
C007 C 0.5643(4) 0.5923(3) 0.75910(15) 0.0378(7) Uani 1 1 d . . . . .
O008 O 0.4209(6) 0.7581(4) 0.56805(19) 0.0855(11) Uani 1 1 d . . . . .
C009 C 0.1651(4) 0.6539(4) 0.73990(18) 0.0471(8) Uani 1 1 d . . . . .
C00A C 0.4598(4) 0.6582(4) 0.59718(15) 0.0439(7) Uani 1 1 d . . . . .
C00B C 0.3924(4) 0.6192(3) 0.66353(16) 0.0415(7) Uani 1 1 d . . . . .
H00B H 0.3903 0.5185 0.6670 0.050 Uiso 1 1 calc R . . . .
C00C C 0.1571(4) 0.5222(4) 0.76681(19) 0.0479(8) Uani 1 1 d . . . . .
H00C H 0.1666 0.4448 0.7406 0.057 Uiso 1 1 calc R . . . .
C00D C 0.1146(4) 0.6200(4) 0.87341(19) 0.0505(9) Uani 1 1 d . . . . .
C00E C 0.6707(5) 0.6663(4) 0.80653(19) 0.0495(8) Uani 1 1 d . . . . .
H00A H 0.6451 0.7638 0.8054 0.059 Uiso 1 1 calc R . . . .
H00D H 0.7818 0.6559 0.7930 0.059 Uiso 1 1 calc R . . . .
C00F C 0.1352(4) 0.5069(4) 0.83240(19) 0.0481(8) Uani 1 1 d . . . . .
C00G C 0.1357(5) 0.7657(4) 0.7790(2) 0.0514(9) Uani 1 1 d . . . . .
H00G H 0.1350 0.8539 0.7614 0.062 Uiso 1 1 calc R . . . .
C00H C 0.2203(5) 0.6733(5) 0.67153(18) 0.0510(9) Uani 1 1 d . . . . .
H00E H 0.2167 0.7704 0.6605 0.061 Uiso 1 1 calc R . . . .
H00F H 0.1489 0.6242 0.6425 0.061 Uiso 1 1 calc R . . . .
C00I C 0.6550(5) 0.6148(4) 0.87650(18) 0.0511(9) Uani 1 1 d . . . . .
H00H H 0.6565 0.5148 0.8765 0.061 Uiso 1 1 calc R . . . .
H00I H 0.7475 0.6463 0.9010 0.061 Uiso 1 1 calc R . . . .
C00J C 0.1071(5) 0.7477(4) 0.8443(2) 0.0535(9) Uani 1 1 d . . . . .
C00K C 0.5047(5) 0.6632(4) 0.90941(18) 0.0526(9) Uani 1 1 d . . . . .
H00K H 0.4827 0.7572 0.9077 0.063 Uiso 1 1 calc R . . . .
C00L C 0.2536(6) 0.6402(6) 0.9723(2) 0.0668(12) Uani 1 1 d . . . . .
H00J H 0.2489 0.6049 1.0161 0.080 Uiso 1 1 calc R . . . .
H00L H 0.2602 0.7399 0.9748 0.080 Uiso 1 1 calc R . . . .
C00M C 0.4020(5) 0.5863(5) 0.94016(19) 0.0551(9) Uani 1 1 d . . . . .
H00M H 0.4221 0.4921 0.9423 0.066 Uiso 1 1 calc R . . . .
C00N C 0.6524(7) 0.6055(6) 0.5183(2) 0.0739(13) Uani 1 1 d . . . . .
H00N H 0.5763 0.6007 0.4835 0.111 Uiso 1 1 calc GR . . . .
H00O H 0.7377 0.5407 0.5109 0.111 Uiso 1 1 calc GR . . . .
H00P H 0.6962 0.6969 0.5207 0.111 Uiso 1 1 calc GR . . . .


_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
Cl01 C00F 1.729(4) . ?
Cl02 C00J 1.736(4) . ?
O003 C007 1.215(4) . ?
N004 H004 0.8600 . ?
N004 C007 1.345(4) . ?
N004 C00B 1.455(4) . ?
O005 C00D 1.358(5) . ?
O005 C00L 1.462(6) . ?
O006 C00A 1.307(5) . ?
O006 C00N 1.452(5) . ?
C007 C00E 1.504(5) . ?
O008 C00A 1.186(5) . ?
C009 C00C 1.396(6) . ?
C009 C00G 1.376(6) . ?
C009 C00H 1.501(5) . ?
C00A C00B 1.531(5) . ?
C00B H00B 0.9800 . ?
C00B C00H 1.531(5) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.379(5) . ?
C00D C00F 1.399(6) . ?
C00D C00J 1.379(6) . ?
C00E H00A 0.9700 . ?
C00E H00D 0.9700 . ?
C00E C00I 1.539(5) . ?
C00G H00G 0.9300 . ?
C00G C00J 1.386(7) . ?
C00H H00E 0.9700 . ?
C00H H00F 0.9700 . ?
C00I H00H 0.9700 . ?
C00I H00I 0.9700 . ?
C00I C00K 1.499(6) . ?
C00K H00K 0.9300 . ?
C00K C00M 1.300(6) . ?
C00L H00J 0.9700 . ?
C00L H00L 0.9700 . ?
C00L C00M 1.496(6) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9600 . ?
C00N H00O 0.9600 . ?
C00N H00P 0.9600 . ?

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
C007 N004 H004 118.8 . . ?
C007 N004 C00B 122.5(3) . . ?
C00B N004 H004 118.8 . . ?
C00D O005 C00L 113.5(3) . . ?
C00A O006 C00N 116.2(4) . . ?
O003 C007 N004 123.0(3) . . ?
O003 C007 C00E 122.1(3) . . ?
N004 C007 C00E 114.9(3) . . ?
C00C C009 C00H 120.4(3) . . ?
C00G C009 C00C 118.6(4) . . ?
C00G C009 C00H 120.7(4) . . ?
O006 C00A C00B 111.6(3) . . ?
O008 C00A O006 124.3(4) . . ?
O008 C00A C00B 124.0(4) . . ?
N004 C00B C00A 109.2(3) . . ?
N004 C00B H00B 108.5 . . ?
N004 C00B C00H 111.3(3) . . ?
C00A C00B H00B 108.5 . . ?
C00H C00B C00A 110.7(3) . . ?
C00H C00B H00B 108.5 . . ?
C009 C00C H00C 120.1 . . ?
C00F C00C C009 119.9(4) . . ?
C00F C00C H00C 120.1 . . ?
O005 C00D C00F 120.5(4) . . ?
O005 C00D C00J 123.1(4) . . ?
C00J C00D C00F 116.4(4) . . ?
C007 C00E H00A 108.7 . . ?
C007 C00E H00D 108.7 . . ?
C007 C00E C00I 114.3(3) . . ?
H00A C00E H00D 107.6 . . ?
C00I C00E H00A 108.7 . . ?
C00I C00E H00D 108.7 . . ?
C00C C00F Cl01 118.5(3) . . ?
C00C C00F C00D 122.0(4) . . ?
C00D C00F Cl01 119.4(3) . . ?
C009 C00G H00G 119.8 . . ?
C009 C00G C00J 120.4(4) . . ?
C00J C00G H00G 119.8 . . ?
C009 C00H C00B 110.2(3) . . ?
C009 C00H H00E 109.6 . . ?
C009 C00H H00F 109.6 . . ?
C00B C00H H00E 109.6 . . ?
C00B C00H H00F 109.6 . . ?
H00E C00H H00F 108.1 . . ?
C00E C00I H00H 108.9 . . ?
C00E C00I H00I 108.9 . . ?
H00H C00I H00I 107.7 . . ?
C00K C00I C00E 113.4(3) . . ?
C00K C00I H00H 108.9 . . ?
C00K C00I H00I 108.9 . . ?
C00D C00J Cl02 118.9(3) . . ?
C00D C00J C00G 122.2(4) . . ?
C00G C00J Cl02 119.0(3) . . ?
C00I C00K H00K 116.9 . . ?
C00M C00K C00I 126.1(4) . . ?
C00M C00K H00K 116.9 . . ?
O005 C00L H00J 109.0 . . ?
O005 C00L H00L 109.0 . . ?
O005 C00L C00M 112.9(3) . . ?
H00J C00L H00L 107.8 . . ?
C00M C00L H00J 109.0 . . ?
C00M C00L H00L 109.0 . . ?
C00K C00M C00L 123.9(4) . . ?
C00K C00M H00M 118.0 . . ?
C00L C00M H00M 118.0 . . ?
O006 C00N H00N 109.5 . . ?
O006 C00N H00O 109.5 . . ?
O006 C00N H00P 109.5 . . ?
H00N C00N H00O 109.5 . . ?
H00N C00N H00P 109.5 . . ?
H00O C00N H00P 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O003 C007 C00E C00I -41.3(5) . . . . ?
N004 C007 C00E C00I 141.0(3) . . . . ?
N004 C00B C00H C009 -49.6(4) . . . . ?
O005 C00D C00F Cl01 1.6(5) . . . . ?
O005 C00D C00F C00C -174.8(3) . . . . ?
O005 C00D C00J Cl02 -6.6(5) . . . . ?
O005 C00D C00J C00G 172.0(4) . . . . ?
O005 C00L C00M C00K 108.6(5) . . . . ?
O006 C00A C00B N004 82.6(4) . . . . ?
O006 C00A C00B C00H -154.5(3) . . . . ?
C007 N004 C00B C00A -124.2(3) . . . . ?
C007 N004 C00B C00H 113.2(4) . . . . ?
C007 C00E C00I C00K -75.7(4) . . . . ?
O008 C00A C00B N004 -93.6(5) . . . . ?
O008 C00A C00B C00H 29.3(5) . . . . ?
C009 C00C C00F Cl01 -174.2(3) . . . . ?
C009 C00C C00F C00D 2.3(5) . . . . ?
C009 C00G C00J Cl02 -178.1(3) . . . . ?
C009 C00G C00J C00D 3.3(6) . . . . ?
C00A C00B C00H C009 -171.3(3) . . . . ?
C00B N004 C007 O003 2.2(5) . . . . ?
C00B N004 C007 C00E 179.8(3) . . . . ?
C00C C009 C00G C00J 3.3(5) . . . . ?
C00C C009 C00H C00B -60.3(4) . . . . ?
C00D O005 C00L C00M -45.3(6) . . . . ?
C00E C00I C00K C00M 129.3(4) . . . . ?
C00F C00D C00J Cl02 174.6(3) . . . . ?
C00F C00D C00J C00G -6.8(5) . . . . ?
C00G C009 C00C C00F -6.0(5) . . . . ?
C00G C009 C00H C00B 113.6(4) . . . . ?
C00H C009 C00C C00F 168.1(3) . . . . ?
C00H C009 C00G C00J -170.8(3) . . . . ?
C00I C00K C00M C00L 179.9(4) . . . . ?
C00J C00D C00F Cl01 -179.5(3) . . . . ?
C00J C00D C00F C00C 4.0(5) . . . . ?
C00L O005 C00D C00F 103.7(4) . . . . ?
C00L O005 C00D C00J -75.1(5) . . . . ?
C00N O006 C00A O008 0.4(7) . . . . ?
C00N O006 C00A C00B -175.7(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-12
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_lliubo-slq-7043
_database_code_depnum_ccdc_archive 'CCDC 1436896'
_audit_update_record             
;
2015-11-13 deposited with the CCDC.
2015-12-22 downloaded from the CCDC.
;
_audit_creation_date             2015-11-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 Br2 N O4'
_chemical_formula_sum            'C16 H17 Br2 N O4'
_chemical_formula_weight         447.12
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.3327(7)
_cell_length_b                   9.5492(9)
_cell_length_c                   11.4501(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.133(9)
_cell_angle_gamma                90
_cell_volume                     865.83(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3461
_cell_measurement_temperature    292.36(10)
_cell_measurement_theta_max      72.1150
_cell_measurement_theta_min      4.5920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8597
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         5.587
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.36(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00  104.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  -31.00   53.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   75.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   30.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega   20.00  104.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega  -33.00   55.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000   30.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega   17.00  105.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
  7 omega  -31.00   53.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  8 omega   10.00  104.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -30.0000 94

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   98.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   81.00  176.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 95

#__ type_ start__ end____ width___ exp.time_
 11 omega   90.00  175.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
 12 omega   91.00  176.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   91.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega   70.00  178.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 108

#__ type_ start__ end____ width___ exp.time_
 15 omega   39.00  109.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
 16 omega   87.00  178.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 91

#__ type_ start__ end____ width___ exp.time_
 17 omega   81.00  158.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 77

#__ type_ start__ end____ width___ exp.time_
 18 omega   90.00  116.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   82.00  109.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega  129.00  175.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
 21 omega   88.00  121.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
 22 omega   88.00  113.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   91.00  116.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega  147.00  173.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega  128.00  175.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
 26 omega   92.00  161.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 69

#__ type_ start__ end____ width___ exp.time_
 27 omega   91.00  116.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 28 omega   92.00  118.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   82.00  109.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 30 omega   39.00  103.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 64

#__ type_ start__ end____ width___ exp.time_
 31 omega   91.00  117.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   91.00  123.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
 33 omega   92.00  117.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 34 omega   81.00  107.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 35 omega   43.00   69.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega   71.00  105.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 37 omega   89.00  114.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 38 omega   71.00   97.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 39 omega  116.00  178.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0059966000
_diffrn_orient_matrix_UB_12      0.0500985000
_diffrn_orient_matrix_UB_13      -0.1265145000
_diffrn_orient_matrix_UB_21      -0.1936187000
_diffrn_orient_matrix_UB_22      -0.0125533000
_diffrn_orient_matrix_UB_23      -0.0516754000
_diffrn_orient_matrix_UB_31      -0.0175945000
_diffrn_orient_matrix_UB_32      0.1528426000
_diffrn_orient_matrix_UB_33      0.0372010000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.836
_reflns_Friedel_fraction_max     0.836
_reflns_number_gt                2691
_reflns_number_total             2858
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 
;
 Flack x determined using 1028 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0819P)²+0.1463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1290
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00c,H00d), C00D(H00e,H00f), C00E(H00g,H00h), C00M(H00k,H00l)
2.c Aromatic/amide H refined with riding coordinates:
 N006(H006), C009(H009), C00A(H00A), C00F(H00i), C00I(H00j)
2.d Idealised Me refined as rotating group:
 C00N(H00m,H00n,H00o)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br01 Br 0.96783(14) 0.79595(10) 0.79984(9) 0.0772(3) Uani 1 1 d . . . . .
Br02 Br 0.89931(15) 0.20411(11) 0.80425(10) 0.0823(4) Uani 1 1 d . . . . .
O003 O 0.4842(7) 0.6867(6) 0.5136(5) 0.0545(11) Uani 1 1 d . . . . .
O004 O 0.9369(6) 0.5099(7) 0.9053(4) 0.0588(13) Uani 1 1 d . . . . .
O005 O 0.4312(8) 0.4435(8) 0.1679(5) 0.0677(16) Uani 1 1 d . . . . .
N006 N 0.5047(7) 0.4897(6) 0.4089(4) 0.0419(11) Uani 1 1 d . . . . .
H006 H 0.4752 0.4035 0.3946 0.050 Uiso 1 1 calc R . . . .
O007 O 0.5897(11) 0.6201(10) 0.1423(6) 0.091(2) Uani 1 1 d . . . . .
C008 C 0.4493(7) 0.5637(8) 0.4893(5) 0.0403(13) Uani 1 1 d . . . . .
C009 C 0.8998(7) 0.6196(9) 0.5917(6) 0.0495(16) Uani 1 1 d . . . . .
H009 H 0.9052 0.7023 0.5501 0.059 Uiso 1 1 calc R . . . .
C00A C 0.8671(8) 0.3709(9) 0.5929(7) 0.0509(16) Uani 1 1 d . . . . .
H00A H 0.8484 0.2855 0.5518 0.061 Uiso 1 1 calc R . . . .
C00B C 0.6135(8) 0.5536(9) 0.3463(6) 0.0483(15) Uani 1 1 d . . . . .
H00B H 0.6231 0.6532 0.3679 0.058 Uiso 1 1 calc R . . . .
C00C C 0.7945(9) 0.4912(10) 0.3900(6) 0.0548(17) Uani 1 1 d . . . . .
H00C H 0.7922 0.3958 0.3606 0.066 Uiso 1 1 calc R . . . .
H00D H 0.8680 0.5456 0.3563 0.066 Uiso 1 1 calc R . . . .
C00D C 0.3473(8) 0.5295(10) 0.6751(6) 0.0538(18) Uani 1 1 d . . . . .
H00E H 0.3457 0.6310 0.6781 0.065 Uiso 1 1 calc R . . . .
H00F H 0.2505 0.4953 0.6965 0.065 Uiso 1 1 calc R . . . .
C00E C 0.3313(8) 0.4828(8) 0.5429(6) 0.0448(14) Uani 1 1 d . . . . .
H00G H 0.3567 0.3837 0.5431 0.054 Uiso 1 1 calc R . . . .
H00H H 0.2157 0.4964 0.4910 0.054 Uiso 1 1 calc R . . . .
C00F C 0.5056(9) 0.4772(10) 0.7678(6) 0.0539(18) Uani 1 1 d . . . . .
H00I H 0.5170 0.3806 0.7771 0.065 Uiso 1 1 calc R . . . .
C00G C 0.8621(8) 0.4931(9) 0.5286(6) 0.0481(15) Uani 1 1 d . . . . .
C00H C 0.9000(7) 0.3751(9) 0.7194(7) 0.0513(16) Uani 1 1 d . . . . .
C00I C 0.6295(9) 0.5533(10) 0.8371(7) 0.0561(17) Uani 1 1 d . . . . .
H00J H 0.6239 0.6499 0.8262 0.067 Uiso 1 1 calc R . . . .
C00J C 0.9218(8) 0.5005(11) 0.7843(6) 0.0508(16) Uani 1 1 d . . . . .
C00K C 0.9288(7) 0.6199(9) 0.7170(6) 0.0491(15) Uani 1 1 d . . . . .
C00L C 0.5428(8) 0.5442(10) 0.2069(6) 0.0518(17) Uani 1 1 d . . . . .
C00M C 0.7791(10) 0.4938(12) 0.9325(6) 0.062(2) Uani 1 1 d . . . . .
H00K H 0.7898 0.5390 1.0104 0.075 Uiso 1 1 calc R . . . .
H00L H 0.7596 0.3949 0.9418 0.075 Uiso 1 1 calc R . . . .
C00N C 0.3592(14) 0.4289(16) 0.0353(8) 0.089(4) Uani 1 1 d . . . . .
H00M H 0.3301 0.5197 -0.0012 0.134 Uiso 1 1 calc GR . . . .
H00N H 0.2597 0.3717 0.0167 0.134 Uiso 1 1 calc GR . . . .
H00O H 0.4404 0.3857 0.0029 0.134 Uiso 1 1 calc GR . . . .


_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
Br01 C00K 1.908(8) . ?
Br02 C00H 1.901(8) . ?
O003 C008 1.221(9) . ?
O004 C00J 1.354(9) . ?
O004 C00M 1.451(10) . ?
O005 C00L 1.315(10) . ?
O005 C00N 1.456(10) . ?
N006 H006 0.8600 . ?
N006 C008 1.351(8) . ?
N006 C00B 1.454(9) . ?
O007 C00L 1.186(11) . ?
C008 C00E 1.522(9) . ?
C009 H009 0.9300 . ?
C009 C00G 1.393(12) . ?
C009 C00K 1.379(10) . ?
C00A H00A 0.9300 . ?
C00A C00G 1.373(12) . ?
C00A C00H 1.388(11) . ?
C00B H00B 0.9800 . ?
C00B C00C 1.552(10) . ?
C00B C00L 1.522(9) . ?
C00C H00C 0.9700 . ?
C00C H00D 0.9700 . ?
C00C C00G 1.510(9) . ?
C00D H00E 0.9700 . ?
C00D H00F 0.9700 . ?
C00D C00E 1.543(9) . ?
C00D C00F 1.499(10) . ?
C00E H00G 0.9700 . ?
C00E H00H 0.9700 . ?
C00F H00I 0.9300 . ?
C00F C00I 1.309(12) . ?
C00H C00J 1.391(13) . ?
C00I H00J 0.9300 . ?
C00I C00M 1.491(10) . ?
C00J C00K 1.388(13) . ?
C00M H00K 0.9700 . ?
C00M H00L 0.9700 . ?
C00N H00M 0.9600 . ?
C00N H00N 0.9600 . ?
C00N H00O 0.9600 . ?

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
C00J O004 C00M 114.3(5) . . ?
C00L O005 C00N 116.3(7) . . ?
C008 N006 H006 119.5 . . ?
C008 N006 C00B 121.0(6) . . ?
C00B N006 H006 119.5 . . ?
O003 C008 N006 123.4(6) . . ?
O003 C008 C00E 122.3(6) . . ?
N006 C008 C00E 114.2(6) . . ?
C00G C009 H009 120.7 . . ?
C00K C009 H009 120.7 . . ?
C00K C009 C00G 118.7(7) . . ?
C00G C00A H00A 120.1 . . ?
C00G C00A C00H 119.9(7) . . ?
C00H C00A H00A 120.1 . . ?
N006 C00B H00B 107.3 . . ?
N006 C00B C00C 111.9(6) . . ?
N006 C00B C00L 113.3(6) . . ?
C00C C00B H00B 107.3 . . ?
C00L C00B H00B 107.3 . . ?
C00L C00B C00C 109.6(5) . . ?
C00B C00C H00C 109.7 . . ?
C00B C00C H00D 109.7 . . ?
H00C C00C H00D 108.2 . . ?
C00G C00C C00B 110.0(5) . . ?
C00G C00C H00C 109.7 . . ?
C00G C00C H00D 109.7 . . ?
H00E C00D H00F 107.8 . . ?
C00E C00D H00E 109.0 . . ?
C00E C00D H00F 109.0 . . ?
C00F C00D H00E 109.0 . . ?
C00F C00D H00F 109.0 . . ?
C00F C00D C00E 112.8(6) . . ?
C008 C00E C00D 112.3(5) . . ?
C008 C00E H00G 109.1 . . ?
C008 C00E H00H 109.1 . . ?
C00D C00E H00G 109.1 . . ?
C00D C00E H00H 109.1 . . ?
H00G C00E H00H 107.9 . . ?
C00D C00F H00I 116.6 . . ?
C00I C00F C00D 126.8(9) . . ?
C00I C00F H00I 116.6 . . ?
C009 C00G C00C 120.4(7) . . ?
C00A C00G C009 119.6(6) . . ?
C00A C00G C00C 119.5(7) . . ?
C00A C00H Br02 118.5(6) . . ?
C00A C00H C00J 122.2(7) . . ?
C00J C00H Br02 119.1(6) . . ?
C00F C00I H00J 118.2 . . ?
C00F C00I C00M 123.7(9) . . ?
C00M C00I H00J 118.2 . . ?
O004 C00J C00H 123.9(8) . . ?
O004 C00J C00K 120.5(8) . . ?
C00K C00J C00H 115.6(6) . . ?
C009 C00K Br01 117.8(7) . . ?
C009 C00K C00J 123.5(8) . . ?
C00J C00K Br01 118.5(5) . . ?
O005 C00L C00B 113.7(6) . . ?
O007 C00L O005 124.8(7) . . ?
O007 C00L C00B 121.5(8) . . ?
O004 C00M C00I 114.2(6) . . ?
O004 C00M H00K 108.7 . . ?
O004 C00M H00L 108.7 . . ?
C00I C00M H00K 108.7 . . ?
C00I C00M H00L 108.7 . . ?
H00K C00M H00L 107.6 . . ?
O005 C00N H00M 109.5 . . ?
O005 C00N H00N 109.5 . . ?
O005 C00N H00O 109.5 . . ?
H00M C00N H00N 109.5 . . ?
H00M C00N H00O 109.5 . . ?
H00N C00N H00O 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br02 C00H C00J O004 -2.5(9) . . . . ?
Br02 C00H C00J C00K 177.1(5) . . . . ?
O003 C008 C00E C00D -34.4(8) . . . . ?
O004 C00J C00K Br01 2.1(8) . . . . ?
O004 C00J C00K C009 -174.1(6) . . . . ?
N006 C008 C00E C00D 148.6(5) . . . . ?
N006 C00B C00C C00G -50.5(9) . . . . ?
N006 C00B C00L O005 -21.7(10) . . . . ?
N006 C00B C00L O007 159.8(9) . . . . ?
C008 N006 C00B C00C 111.6(7) . . . . ?
C008 N006 C00B C00L -123.9(7) . . . . ?
C00A C00H C00J O004 173.0(6) . . . . ?
C00A C00H C00J C00K -7.4(9) . . . . ?
C00B N006 C008 O003 0.8(9) . . . . ?
C00B N006 C008 C00E 177.8(5) . . . . ?
C00B C00C C00G C009 -68.3(9) . . . . ?
C00B C00C C00G C00A 103.7(8) . . . . ?
C00C C00B C00L O005 104.0(8) . . . . ?
C00C C00B C00L O007 -74.5(11) . . . . ?
C00D C00F C00I C00M 176.5(6) . . . . ?
C00E C00D C00F C00I 116.9(8) . . . . ?
C00F C00D C00E C008 -74.4(8) . . . . ?
C00F C00I C00M O004 113.1(9) . . . . ?
C00G C009 C00K Br01 -176.6(5) . . . . ?
C00G C009 C00K C00J -0.3(9) . . . . ?
C00G C00A C00H Br02 178.2(5) . . . . ?
C00G C00A C00H C00J 2.7(10) . . . . ?
C00H C00A C00G C009 3.7(9) . . . . ?
C00H C00A C00G C00C -168.5(6) . . . . ?
C00H C00J C00K Br01 -177.5(4) . . . . ?
C00H C00J C00K C009 6.3(9) . . . . ?
C00J O004 C00M C00I -34.8(11) . . . . ?
C00K C009 C00G C00A -4.8(9) . . . . ?
C00K C009 C00G C00C 167.3(6) . . . . ?
C00L C00B C00C C00G -177.0(7) . . . . ?
C00M O004 C00J C00H -76.1(9) . . . . ?
C00M O004 C00J C00K 104.4(9) . . . . ?
C00N O005 C00L O007 -1.4(14) . . . . ?
C00N O005 C00L C00B -179.8(8) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-09
_olex2_submission_special_instructions 'No special instructions were received'
