# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_N-IPBADC

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'N-Isopropylbenzylammonium Dichloroacetate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 N, C2 H Cl2 O2'
_chemical_formula_sum            'C12 H17 Cl2 N O2'
_chemical_formula_weight         278.17

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   9.700(8)
_cell_length_b                   8.569(6)
_cell_length_c                   17.378(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.825(13)
_cell_angle_gamma                90.00
_cell_volume                     1389.7(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584.0
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10400
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3196
_reflns_number_gt                2453
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0794P)²+0.5512P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3168
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1507
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.12596(9) 0.33616(9) 0.01023(5) 0.0777(3) Uani 1 1 d . . .
Cl1 Cl 0.18982(9) 0.01133(9) -0.00728(5) 0.0773(3) Uani 1 1 d . . .
N1 N -0.44732(18) 0.2413(2) -0.19703(11) 0.0413(4) Uani 1 1 d . . .
H8A H -0.4215 0.1450 -0.1743 0.050 Uiso 1 1 calc R . .
H8B H -0.4996 0.2253 -0.2492 0.050 Uiso 1 1 calc R . .
O2 O 0.3734(2) 0.31438(19) 0.14721(12) 0.0694(6) Uani 1 1 d . . .
C12 C 0.3376(2) 0.1827(3) 0.12300(14) 0.0460(5) Uani 1 1 d . . .
O1 O 0.4023(2) 0.0615(2) 0.14665(13) 0.0716(6) Uani 1 1 d . . .
C6 C -0.2254(2) 0.2383(3) -0.24039(14) 0.0455(5) Uani 1 1 d . . .
C7 C -0.3146(3) 0.3285(3) -0.19726(18) 0.0567(6) Uani 1 1 d . . .
H7A H -0.2578 0.3480 -0.1415 0.068 Uiso 1 1 calc R . .
H7B H -0.3408 0.4308 -0.2237 0.068 Uiso 1 1 calc R . .
C11 C 0.1902(3) 0.1633(3) 0.06156(14) 0.0506(6) Uani 1 1 d . . .
H12 H 0.1207 0.1330 0.0922 0.061 Uiso 1 1 calc R . .
C1 C -0.1107(3) 0.1509(3) -0.19767(15) 0.0542(6) Uani 1 1 d . . .
H1 H -0.0885 0.1477 -0.1410 0.065 Uiso 1 1 calc R . .
C8 C -0.5420(3) 0.3203(3) -0.15309(16) 0.0531(6) Uani 1 1 d . . .
H11 H -0.5619 0.4290 -0.1741 0.064 Uiso 1 1 calc R . .
C2 C -0.0279(3) 0.0685(3) -0.23638(17) 0.0646(7) Uani 1 1 d . . .
H2 H 0.0504 0.0079 -0.2063 0.078 Uiso 1 1 calc R . .
C5 C -0.2553(3) 0.2422(3) -0.32272(15) 0.0568(6) Uani 1 1 d . . .
H5 H -0.3343 0.3015 -0.3530 0.068 Uiso 1 1 calc R . .
C10 C -0.6817(3) 0.2323(4) -0.1711(2) 0.0736(8) Uani 1 1 d . . .
H10A H -0.6638 0.1250 -0.1514 0.110 Uiso 1 1 calc R . .
H10B H -0.7256 0.2310 -0.2290 0.110 Uiso 1 1 calc R . .
H10C H -0.7465 0.2838 -0.1445 0.110 Uiso 1 1 calc R . .
C3 C -0.0578(3) 0.0733(4) -0.31780(19) 0.0675(7) Uani 1 1 d . . .
H3 H -0.0003 0.0163 -0.3443 0.081 Uiso 1 1 calc R . .
C4 C -0.1710(3) 0.1604(4) -0.36125(18) 0.0670(7) Uani 1 1 d . . .
H4 H -0.1913 0.1645 -0.4179 0.080 Uiso 1 1 calc R . .
C9 C -0.4693(4) 0.3286(4) -0.0657(2) 0.0825(10) Uani 1 1 d . . .
H9A H -0.4433 0.2232 -0.0449 0.124 Uiso 1 1 calc R . .
H9B H -0.5343 0.3757 -0.0379 0.124 Uiso 1 1 calc R . .
H9C H -0.3826 0.3925 -0.0569 0.124 Uiso 1 1 calc R . .


_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
Cl2 C11 1.754(3) . ?
Cl1 C11 1.767(3) . ?
N1 C7 1.490(3) . ?
N1 C8 1.506(3) . ?
N1 H8A 0.9200 . ?
N1 H8B 0.9200 . ?
O2 C12 1.221(3) . ?
C12 O1 1.225(3) . ?
C12 C11 1.542(3) . ?
C6 C1 1.378(3) . ?
C6 C5 1.381(4) . ?
C6 C7 1.504(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C11 H12 1.0000 . ?
C1 C2 1.375(4) . ?
C1 H1 0.9500 . ?
C8 C9 1.492(4) . ?
C8 C10 1.507(4) . ?
C8 H11 1.0000 . ?
C2 C3 1.365(4) . ?
C2 H2 0.9500 . ?
C5 C4 1.381(4) . ?
C5 H5 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 115.03(18) . . ?
C7 N1 H8A 108.5 . . ?
C8 N1 H8A 108.5 . . ?
C7 N1 H8B 108.5 . . ?
C8 N1 H8B 108.5 . . ?
H8A N1 H8B 107.5 . . ?
O2 C12 O1 126.6(2) . . ?
O2 C12 C11 117.4(2) . . ?
O1 C12 C11 115.7(2) . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 C7 120.0(2) . . ?
C5 C6 C7 121.2(2) . . ?
N1 C7 C6 110.99(19) . . ?
N1 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C12 C11 Cl2 113.25(16) . . ?
C12 C11 Cl1 112.24(17) . . ?
Cl2 C11 Cl1 110.07(15) . . ?
C12 C11 H12 107.0 . . ?
Cl2 C11 H12 107.0 . . ?
Cl1 C11 H12 107.0 . . ?
C6 C1 C2 120.6(2) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C9 C8 N1 110.7(2) . . ?
C9 C8 C10 112.6(3) . . ?
N1 C8 C10 108.0(2) . . ?
C9 C8 H11 108.5 . . ?
N1 C8 H11 108.5 . . ?
C10 C8 H11 108.5 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
C8 N1 C7 C6 178.3(2) . . . . ?
C1 C6 C7 N1 -98.4(3) . . . . ?
C5 C6 C7 N1 82.2(3) . . . . ?
O2 C12 C11 Cl2 21.4(3) . . . . ?
O1 C12 C11 Cl2 -163.6(2) . . . . ?
O2 C12 C11 Cl1 146.8(2) . . . . ?
O1 C12 C11 Cl1 -38.2(3) . . . . ?
C5 C6 C1 C2 -0.4(4) . . . . ?
C7 C6 C1 C2 -179.7(2) . . . . ?
C7 N1 C8 C9 -66.3(3) . . . . ?
C7 N1 C8 C10 170.0(2) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C1 C6 C5 C4 -0.3(4) . . . . ?
C7 C6 C5 C4 179.0(2) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C6 C5 C4 C3 0.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 974660'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_N-IPBADC-323K

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'N-Isopropylbenzylammonium Dichloroacetate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 N, C2 H Cl2 O2'
_chemical_formula_sum            'C12 H17 Cl2 N O2'
_chemical_formula_weight         278.17

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   9.7598(3)
_cell_length_b                   8.5995(2)
_cell_length_c                   17.5609(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.105(4)
_cell_angle_gamma                90.00
_cell_volume                     1416.03(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    323(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      323(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8874
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2894
_reflns_number_gt                2082
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1143P)²+0.5631P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2886
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.2137
_refine_ls_wR_factor_gt          0.1916
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.37400(12) 0.33626(11) 0.48877(6) 0.0930(4) Uani 1 1 d . . .
Cl2 Cl 0.30925(12) 0.01284(12) 0.50727(6) 0.0918(4) Uani 1 1 d . . .
O1 O 0.1272(3) 0.3127(2) 0.35193(15) 0.0788(7) Uani 1 1 d . . .
O2 O 0.0993(3) 0.0615(2) 0.35265(15) 0.0798(7) Uani 1 1 d . . .
C10 C -0.0406(3) 0.6794(3) 0.3464(2) 0.0610(8) Uani 1 1 d . . .
H10 H -0.0608 0.5713 0.3253 0.073 Uiso 1 1 calc R . .
N1 N 0.0533(2) 0.7586(2) 0.30289(13) 0.0471(5) Uani 1 1 d . . .
H1A H 0.0010 0.7741 0.2512 0.057 Uiso 1 1 calc R . .
H1B H 0.0786 0.8548 0.3253 0.057 Uiso 1 1 calc R . .
C8 C 0.2746(3) 0.7616(3) 0.25991(17) 0.0510(6) Uani 1 1 d . . .
C9 C 0.1859(3) 0.6721(3) 0.3031(2) 0.0638(8) Uani 1 1 d . . .
H9A H 0.1601 0.5697 0.2772 0.077 Uiso 1 1 calc R . .
H9B H 0.2428 0.6535 0.3584 0.077 Uiso 1 1 calc R . .
C4 C 0.4708(3) 0.9316(4) 0.2636(2) 0.0764(10) Uani 1 1 d . . .
H4 H 0.5488 0.9924 0.2932 0.092 Uiso 1 1 calc R . .
C7 C 0.2440(3) 0.7573(4) 0.17824(19) 0.0644(8) Uani 1 1 d . . .
H7 H 0.1654 0.6978 0.1483 0.077 Uiso 1 1 calc R . .
C6 C 0.3275(4) 0.8393(4) 0.1399(2) 0.0774(10) Uani 1 1 d . . .
H6 H 0.3066 0.8353 0.0837 0.093 Uiso 1 1 calc R . .
C2 C 0.1626(3) 0.1822(3) 0.37667(17) 0.0533(7) Uani 1 1 d . . .
C3 C 0.3891(3) 0.8495(4) 0.30235(19) 0.0621(8) Uani 1 1 d . . .
H3 H 0.4115 0.8533 0.3585 0.075 Uiso 1 1 calc R . .
C1 C 0.3095(3) 0.1637(3) 0.43864(19) 0.0621(8) Uani 1 1 d . . .
H1 H 0.3788 0.1326 0.4089 0.075 Uiso 1 1 calc R . .
C11 C -0.1799(4) 0.7675(5) 0.3287(3) 0.0838(11) Uani 1 1 d . . .
H11A H -0.2455 0.7139 0.3532 0.126 Uiso 1 1 calc R . .
H11B H -0.2223 0.7725 0.2712 0.126 Uiso 1 1 calc R . .
H11C H -0.1623 0.8731 0.3501 0.126 Uiso 1 1 calc R . .
C12 C 0.0329(5) 0.6697(5) 0.4331(3) 0.0933(13) Uani 1 1 d . . .
H12A H 0.1173 0.6031 0.4416 0.140 Uiso 1 1 calc R . .
H12B H -0.0324 0.6256 0.4609 0.140 Uiso 1 1 calc R . .
H12C H 0.0621 0.7741 0.4537 0.140 Uiso 1 1 calc R . .
C5 C 0.4403(4) 0.9261(4) 0.1829(2) 0.0795(10) Uani 1 1 d . . .
H5 H 0.4973 0.9825 0.1565 0.095 Uiso 1 1 calc R . .


_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 C1 1.751(3) . ?
Cl2 C1 1.771(3) . ?
O1 C2 1.219(3) . ?
O2 C2 1.222(3) . ?
C10 C12 1.495(5) . ?
C10 N1 1.508(3) . ?
C10 C11 1.511(5) . ?
C10 H10 1.0000 . ?
N1 C9 1.493(3) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
C8 C7 1.382(4) . ?
C8 C3 1.383(4) . ?
C8 C9 1.510(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C4 C5 1.366(5) . ?
C4 C3 1.378(5) . ?
C4 H4 0.9500 . ?
C7 C6 1.386(5) . ?
C7 H7 0.9500 . ?
C6 C5 1.370(5) . ?
C6 H6 0.9500 . ?
C2 C1 1.549(4) . ?
C3 H3 0.9500 . ?
C1 H1 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C10 N1 110.7(3) . . ?
C12 C10 C11 112.9(3) . . ?
N1 C10 C11 107.9(2) . . ?
C12 C10 H10 108.4 . . ?
N1 C10 H10 108.4 . . ?
C11 C10 H10 108.4 . . ?
C9 N1 C10 115.0(2) . . ?
C9 N1 H1A 108.5 . . ?
C10 N1 H1A 108.5 . . ?
C9 N1 H1B 108.5 . . ?
C10 N1 H1B 108.5 . . ?
H1A N1 H1B 107.5 . . ?
C7 C8 C3 118.9(3) . . ?
C7 C8 C9 121.2(3) . . ?
C3 C8 C9 119.9(3) . . ?
N1 C9 C8 111.3(2) . . ?
N1 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O1 C2 O2 126.4(3) . . ?
O1 C2 C1 117.4(2) . . ?
O2 C2 C1 115.9(2) . . ?
C4 C3 C8 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C8 C3 H3 119.8 . . ?
C2 C1 Cl1 113.6(2) . . ?
C2 C1 Cl2 112.2(2) . . ?
Cl1 C1 Cl2 110.29(18) . . ?
C2 C1 H1 106.8 . . ?
Cl1 C1 H1 106.8 . . ?
Cl2 C1 H1 106.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C10 N1 C9 65.6(3) . . . . ?
C11 C10 N1 C9 -170.5(3) . . . . ?
C10 N1 C9 C8 -178.7(2) . . . . ?
C7 C8 C9 N1 -81.8(3) . . . . ?
C3 C8 C9 N1 98.5(3) . . . . ?
C3 C8 C7 C6 0.3(4) . . . . ?
C9 C8 C7 C6 -179.4(3) . . . . ?
C8 C7 C6 C5 -0.5(5) . . . . ?
C5 C4 C3 C8 -0.5(5) . . . . ?
C7 C8 C3 C4 0.2(4) . . . . ?
C9 C8 C3 C4 179.9(3) . . . . ?
O1 C2 C1 Cl1 21.1(4) . . . . ?
O2 C2 C1 Cl1 -164.8(3) . . . . ?
O1 C2 C1 Cl2 147.0(3) . . . . ?
O2 C2 C1 Cl2 -38.9(4) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C7 C6 C5 C4 0.2(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.098
_database_code_depnum_ccdc_archive 'CCDC 987645'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_N-IPBADC-343K

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'N-Isopropylbenzylammonium Dichloroacetate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 N, C2 H Cl2 O2'
_chemical_formula_sum            'C12 H17 Cl2 N O2'
_chemical_formula_weight         278.17

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   9.7856(5)
_cell_length_b                   8.6119(3)
_cell_length_c                   17.6992(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.549(5)
_cell_angle_gamma                90.00
_cell_volume                     1429.77(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    343(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      343(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8983
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2928
_reflns_number_gt                1972
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1407P)²+0.6151P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2928
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0824
_refine_ls_wR_factor_ref         0.2664
_refine_ls_wR_factor_gt          0.2368
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.62597(15) 0.66398(14) 0.01226(8) 0.1104(6) Uani 1 1 d . . .
Cl2 Cl 0.69164(15) 0.98547(15) -0.00738(8) 0.1084(6) Uani 1 1 d . . .
N1 N 0.9458(3) 0.2417(3) 0.19716(15) 0.0541(7) Uani 1 1 d . . .
H1A H 0.9204 0.1458 0.1746 0.065 Uiso 1 1 calc R . .
H1B H 0.9982 0.2258 0.2486 0.065 Uiso 1 1 calc R . .
O1 O 0.8726(3) 0.6882(3) 0.14890(18) 0.0895(9) Uani 1 1 d . . .
O2 O 0.8992(3) 0.9392(3) 0.14781(18) 0.0904(9) Uani 1 1 d . . .
C6 C 0.7255(3) 0.2383(3) 0.2399(2) 0.0585(8) Uani 1 1 d . . .
C11 C 0.8373(4) 0.8183(3) 0.1235(2) 0.0623(8) Uani 1 1 d . . .
C7 C 0.8135(4) 0.3275(4) 0.1968(3) 0.0727(10) Uani 1 1 d . . .
H7A H 0.7561 0.3456 0.1417 0.087 Uiso 1 1 calc R . .
H7B H 0.8394 0.4299 0.2223 0.087 Uiso 1 1 calc R . .
C8 C 1.0394(4) 0.3214(4) 0.1544(2) 0.0695(10) Uani 1 1 d . . .
H8 H 1.0596 0.4291 0.1757 0.083 Uiso 1 1 calc R . .
C1 C 0.7570(4) 0.2434(4) 0.3209(2) 0.0741(10) Uani 1 1 d . . .
H1 H 0.8354 0.3033 0.3507 0.089 Uiso 1 1 calc R . .
C12 C 0.6916(4) 0.8354(4) 0.0610(2) 0.0760(11) Uani 1 1 d . . .
H12 H 0.6223 0.8675 0.0901 0.091 Uiso 1 1 calc R . .
C5 C 0.6117(4) 0.1497(5) 0.1976(2) 0.0715(10) Uani 1 1 d . . .
H5 H 0.5891 0.1449 0.1418 0.086 Uiso 1 1 calc R . .
C9 C 1.1784(5) 0.2340(6) 0.1722(3) 0.0938(13) Uani 1 1 d . . .
H9A H 1.1604 0.1276 0.1521 0.141 Uiso 1 1 calc R . .
H9B H 1.2224 0.2312 0.2293 0.141 Uiso 1 1 calc R . .
H9C H 1.2426 0.2861 0.1468 0.141 Uiso 1 1 calc R . .
C4 C 0.5309(4) 0.0684(5) 0.2363(3) 0.0881(12) Uani 1 1 d . . .
H4 H 0.4532 0.0070 0.2070 0.106 Uiso 1 1 calc R . .
C2 C 0.6743(5) 0.1611(5) 0.3589(3) 0.0875(12) Uani 1 1 d . . .
H2 H 0.6964 0.1647 0.4147 0.105 Uiso 1 1 calc R . .
C3 C 0.5616(5) 0.0752(6) 0.3167(3) 0.0916(13) Uani 1 1 d . . .
H3 H 0.5045 0.0201 0.3430 0.110 Uiso 1 1 calc R . .
C10 C 0.9635(6) 0.3321(6) 0.0677(3) 0.1042(16) Uani 1 1 d . . .
H10A H 1.0289 0.3729 0.0397 0.156 Uiso 1 1 calc R . .
H10B H 0.8813 0.4017 0.0596 0.156 Uiso 1 1 calc R . .
H10C H 0.9307 0.2286 0.0474 0.156 Uiso 1 1 calc R . .


_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 C12 1.738(4) . ?
Cl2 C12 1.771(4) . ?
N1 C7 1.488(4) . ?
N1 C8 1.509(4) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
O1 C11 1.220(4) . ?
O2 C11 1.220(4) . ?
C6 C1 1.379(5) . ?
C6 C5 1.381(5) . ?
C6 C7 1.513(5) . ?
C11 C12 1.542(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.504(6) . ?
C8 C9 1.507(6) . ?
C8 H8 1.0000 . ?
C1 C2 1.385(6) . ?
C1 H1 0.9500 . ?
C12 H12 1.0000 . ?
C5 C4 1.376(6) . ?
C5 H5 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C4 C3 1.369(6) . ?
C4 H4 0.9500 . ?
C2 C3 1.361(6) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 115.0(2) . . ?
C7 N1 H1A 108.5 . . ?
C8 N1 H1A 108.5 . . ?
C7 N1 H1B 108.5 . . ?
C8 N1 H1B 108.5 . . ?
H1A N1 H1B 107.5 . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 C7 121.1(3) . . ?
C5 C6 C7 119.7(3) . . ?
O2 C11 O1 126.4(3) . . ?
O2 C11 C12 115.9(3) . . ?
O1 C11 C12 117.3(3) . . ?
N1 C7 C6 111.4(2) . . ?
N1 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C10 C8 C9 113.5(4) . . ?
C10 C8 N1 110.2(3) . . ?
C9 C8 N1 108.0(3) . . ?
C10 C8 H8 108.4 . . ?
C9 C8 H8 108.4 . . ?
N1 C8 H8 108.4 . . ?
C6 C1 C2 120.0(4) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C11 C12 Cl1 114.2(3) . . ?
C11 C12 Cl2 112.3(3) . . ?
Cl1 C12 Cl2 110.7(2) . . ?
C11 C12 H12 106.4 . . ?
Cl1 C12 H12 106.4 . . ?
Cl2 C12 H12 106.4 . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.8(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C8 N1 C7 C6 179.2(3) . . . . ?
C1 C6 C7 N1 81.8(4) . . . . ?
C5 C6 C7 N1 -98.0(4) . . . . ?
C7 N1 C8 C10 -65.2(4) . . . . ?
C7 N1 C8 C9 170.4(3) . . . . ?
C5 C6 C1 C2 -0.5(5) . . . . ?
C7 C6 C1 C2 179.7(3) . . . . ?
O2 C11 C12 Cl1 166.4(3) . . . . ?
O1 C11 C12 Cl1 -20.4(5) . . . . ?
O2 C11 C12 Cl2 39.3(5) . . . . ?
O1 C11 C12 Cl2 -147.5(3) . . . . ?
C1 C6 C5 C4 0.3(5) . . . . ?
C7 C6 C5 C4 -179.9(3) . . . . ?
C6 C5 C4 C3 0.5(6) . . . . ?
C6 C1 C2 C3 -0.1(6) . . . . ?
C1 C2 C3 C4 0.8(7) . . . . ?
C5 C4 C3 C2 -1.0(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.091
_database_code_depnum_ccdc_archive 'CCDC 987646'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_N-IPBADC-358K

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'N-Isopropylbenzylammonium Dichloroacetate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 N, C2 H O2, 2(Cl)'
_chemical_formula_sum            'C12 H17 Cl2 N O2'
_chemical_formula_weight         278.17

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   9.8256(9)
_cell_length_b                   8.6329(5)
_cell_length_c                   17.8841(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.061(8)
_cell_angle_gamma                90.00
_cell_volume                     1450.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    358(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      358(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8979
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2968
_reflns_number_gt                1727
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0681P)²+0.0483P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.042(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2968
_refine_ls_number_parameters     202
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1526
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.027
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.05505(16) -0.24207(16) -0.19723(9) 0.0687(5) Uani 1 1 d . . .
H17A H 0.0804 -0.1463 -0.1750 0.082 Uiso 1 1 d R . .
H17B H 0.0017 -0.2264 -0.2483 0.082 Uiso 1 1 d R . .
C1 C 0.2428(3) -0.2440(3) -0.31979(15) 0.0942(7) Uani 1 1 d . . .
H15 H 0.1646 -0.3041 -0.3495 0.113 Uiso 1 1 calc R . .
C2 C 0.3249(3) -0.1627(3) -0.35716(17) 0.1089(8) Uani 1 1 d . . .
H14 H 0.3033 -0.1684 -0.4125 0.131 Uiso 1 1 calc R . .
C3 C 0.4367(3) -0.0745(4) -0.3157(2) 0.1139(9) Uani 1 1 d . . .
H13 H 0.4926 -0.0188 -0.3419 0.137 Uiso 1 1 calc R . .
C4 C 0.4675(3) -0.0669(3) -0.23659(19) 0.1097(9) Uani 1 1 d . . .
H12 H 0.5444 -0.0043 -0.2075 0.132 Uiso 1 1 calc R . .
C5 C 0.3883(2) -0.1492(3) -0.19814(15) 0.0918(7) Uani 1 1 d . . .
H11 H 0.4126 -0.1446 -0.1427 0.110 Uiso 1 1 calc R . .
C6 C 0.2738(2) -0.2383(2) -0.23926(13) 0.0743(6) Uani 1 1 d . . .
C7 C 0.1875(2) -0.3270(2) -0.19707(15) 0.0898(7) Uani 1 1 d . . .
H16A H 0.1616 -0.4291 -0.2225 0.108 Uiso 1 1 calc R . .
H16B H 0.2457 -0.3453 -0.1424 0.108 Uiso 1 1 calc R . .
C8 C -0.0365(3) -0.3209(2) -0.15499(15) 0.0874(7) Uani 1 1 d . . .
H8 H -0.0574 -0.4280 -0.1767 0.105 Uiso 1 1 calc R . .
C9 C -0.1763(3) -0.2336(4) -0.17226(18) 0.1169(9) Uani 1 1 d . . .
H20A H -0.2194 -0.2263 -0.2290 0.175 Uiso 1 1 calc R . .
H20B H -0.1587 -0.1292 -0.1500 0.175 Uiso 1 1 calc R . .
H20C H -0.2410 -0.2888 -0.1490 0.175 Uiso 1 1 calc R . .
C10 C 0.0384(4) -0.3342(4) -0.06936(19) 0.1289(11) Uani 1 1 d . . .
H19A H 0.0616 -0.2305 -0.0470 0.193 Uiso 1 1 calc R . .
H19B H 0.1262 -0.3940 -0.0616 0.193 Uiso 1 1 calc R . .
H19C H -0.0237 -0.3869 -0.0434 0.193 Uiso 1 1 calc R . .
Cl2 Cl 0.3078(4) -0.9861(3) 0.0066(2) 0.1097(10) Uani 0.68 1 d PU . .
O1 O 0.10244(19) -0.93969(17) -0.14790(11) 0.1104(6) Uani 1 1 d . . .
O2 O 0.12726(19) -0.68934(17) -0.14992(10) 0.1098(6) Uani 1 1 d . . .
C11 C 0.1632(2) -0.8188(2) -0.12343(13) 0.0786(6) Uani 1 1 d . . .
C13 C 0.3127(8) -0.8367(9) -0.0633(5) 0.0680(14) Uani 0.62 1 d P . .
H13A H 0.3880 -0.8824 -0.0840 0.082 Uiso 0.62 1 d PR . .
Cl1 Cl 0.347(3) -0.983(3) 0.0032(16) 0.136(10) Uani 0.07 1 d PU . .
Cl3 Cl 0.2649(14) -0.9510(13) 0.0132(7) 0.214(6) Uani 0.25 1 d PU . .
Cl4 Cl 0.4164(13) -0.733(2) -0.0524(9) 0.197(5) Uani 0.14 1 d PU . .
Cl5 Cl 0.3808(9) -0.6637(9) -0.0214(5) 0.110(2) Uani 0.47 1 d PU . .
Cl6 Cl 0.3641(11) -0.6650(9) -0.0027(6) 0.109(2) Uani 0.39 1 d PU . .
C12 C 0.273(2) -0.820(2) -0.0421(10) 0.138(6) Uani 0.38 1 d P . .
H12A H 0.2053 -0.7818 -0.0140 0.166 Uiso 0.38 1 d PR . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.497(3) . ?
N1 C7 1.493(3) . ?
N1 H17A 0.9200 . ?
N1 H17B 0.9198 . ?
C1 C2 1.381(4) . ?
C1 C6 1.383(3) . ?
C1 H15 0.9500 . ?
C2 C3 1.363(4) . ?
C2 H14 0.9500 . ?
C3 C4 1.359(4) . ?
C3 H13 0.9500 . ?
C4 C5 1.378(4) . ?
C4 H12 0.9500 . ?
C5 C6 1.383(3) . ?
C5 H11 0.9500 . ?
C6 C7 1.500(3) . ?
C7 H16A 0.9900 . ?
C7 H16B 0.9900 . ?
C8 C10 1.496(4) . ?
C8 C9 1.517(4) . ?
C8 H8 1.0000 . ?
C9 H20A 0.9800 . ?
C9 H20B 0.9800 . ?
C9 H20C 0.9800 . ?
C10 H19A 0.9800 . ?
C10 H19B 0.9800 . ?
C10 H19C 0.9800 . ?
Cl2 Cl3 0.559(15) . ?
Cl2 C12 1.657(17) . ?
Cl2 C13 1.807(9) . ?
O1 C11 1.218(2) . ?
O2 C11 1.225(2) . ?
C11 C12 1.535(18) . ?
C11 C13 1.552(9) . ?
C13 C12 0.636(18) . ?
C13 Cl4 1.326(16) . ?
C13 Cl1 1.70(3) . ?
C13 Cl5 1.716(11) . ?
C13 Cl6 1.819(11) . ?
C13 Cl3 1.857(14) . ?
C13 H13A 1.0001 . ?
Cl1 Cl3 0.92(3) . ?
Cl1 C12 1.67(3) . ?
Cl3 C12 1.52(2) . ?
Cl3 H12A 1.5958 . ?
Cl4 Cl5 0.950(17) . ?
Cl4 Cl6 1.29(2) . ?
Cl4 C12 1.66(2) . ?
Cl4 H13A 1.4010 . ?
Cl5 C12 1.69(2) . ?
Cl6 C12 1.65(2) . ?
C12 H12A 1.0000 . ?

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
C8 N1 C7 115.33(15) . . ?
C8 N1 H17A 108.4 . . ?
C7 N1 H17A 108.4 . . ?
C8 N1 H17B 108.4 . . ?
C7 N1 H17B 108.5 . . ?
H17A N1 H17B 107.5 . . ?
C2 C1 C6 120.3(2) . . ?
C2 C1 H15 119.9 . . ?
C6 C1 H15 119.9 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H14 119.6 . . ?
C1 C2 H14 119.6 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H13 120.3 . . ?
C2 C3 H13 120.3 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H12 119.7 . . ?
C5 C4 H12 119.7 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H11 119.6 . . ?
C6 C5 H11 119.6 . . ?
C1 C6 C5 118.0(2) . . ?
C1 C6 C7 121.4(2) . . ?
C5 C6 C7 120.5(2) . . ?
N1 C7 C6 111.67(15) . . ?
N1 C7 H16A 109.3 . . ?
C6 C7 H16A 109.3 . . ?
N1 C7 H16B 109.3 . . ?
C6 C7 H16B 109.3 . . ?
H16A C7 H16B 107.9 . . ?
N1 C8 C10 111.3(2) . . ?
N1 C8 C9 108.26(18) . . ?
C10 C8 C9 113.0(2) . . ?
N1 C8 H8 108.0 . . ?
C10 C8 H8 108.0 . . ?
C9 C8 H8 108.0 . . ?
C8 C9 H20A 109.5 . . ?
C8 C9 H20B 109.5 . . ?
H20A C9 H20B 109.5 . . ?
C8 C9 H20C 109.5 . . ?
H20A C9 H20C 109.5 . . ?
H20B C9 H20C 109.5 . . ?
C8 C10 H19A 109.5 . . ?
C8 C10 H19B 109.5 . . ?
H19A C10 H19B 109.5 . . ?
C8 C10 H19C 109.5 . . ?
H19A C10 H19C 109.5 . . ?
H19B C10 H19C 109.5 . . ?
Cl3 Cl2 C12 65.8(14) . . ?
Cl3 Cl2 C13 86.2(13) . . ?
C12 Cl2 C13 20.6(6) . . ?
O1 C11 O2 126.0(2) . . ?
O1 C11 C12 117.8(7) . . ?
O2 C11 C12 114.7(7) . . ?
O1 C11 C13 115.4(3) . . ?
O2 C11 C13 117.7(3) . . ?
C12 C11 C13 23.8(7) . . ?
C12 C13 Cl4 110(3) . . ?
C12 C13 C11 77(2) . . ?
Cl4 C13 C11 124.4(9) . . ?
C12 C13 Cl1 77(2) . . ?
Cl4 C13 Cl1 114.3(12) . . ?
C11 C13 Cl1 120.8(10) . . ?
C12 C13 Cl5 77(2) . . ?
Cl4 C13 Cl5 33.4(7) . . ?
C11 C13 Cl5 112.6(5) . . ?
Cl1 C13 Cl5 111.6(10) . . ?
C12 C13 Cl2 66(2) . . ?
Cl4 C13 Cl2 123.7(9) . . ?
C11 C13 Cl2 109.8(4) . . ?
Cl1 C13 Cl2 12.8(9) . . ?
Cl5 C13 Cl2 113.9(5) . . ?
C12 C13 Cl6 65(2) . . ?
Cl4 C13 Cl6 45.3(9) . . ?
C11 C13 Cl6 111.9(5) . . ?
Cl1 C13 Cl6 102.9(10) . . ?
Cl5 C13 Cl6 13.0(6) . . ?
Cl2 C13 Cl6 103.2(5) . . ?
C12 C13 Cl3 49(2) . . ?
Cl4 C13 Cl3 126.8(9) . . ?
C11 C13 Cl3 99.8(5) . . ?
Cl1 C13 Cl3 29.4(11) . . ?
Cl5 C13 Cl3 106.9(6) . . ?
Cl2 C13 Cl3 17.5(4) . . ?
Cl6 C13 Cl3 94.6(6) . . ?
C12 C13 H13A 163.6 . . ?
Cl4 C13 H13A 72.5 . . ?
C11 C13 H13A 115.9 . . ?
Cl1 C13 H13A 87.1 . . ?
Cl5 C13 H13A 105.6 . . ?
Cl2 C13 H13A 98.4 . . ?
Cl6 C13 H13A 115.8 . . ?
Cl3 C13 H13A 115.9 . . ?
Cl3 Cl1 C12 64.1(17) . . ?
Cl3 Cl1 C13 84.9(18) . . ?
C12 Cl1 C13 21.7(7) . . ?
Cl2 Cl3 Cl1 15.7(18) . . ?
Cl2 Cl3 C12 94.5(17) . . ?
Cl1 Cl3 C12 83(2) . . ?
Cl2 Cl3 C13 76.3(14) . . ?
Cl1 Cl3 C13 65.6(19) . . ?
C12 Cl3 C13 18.4(7) . . ?
Cl2 Cl3 H12A 131.6 . . ?
Cl1 Cl3 H12A 118.6 . . ?
C12 Cl3 H12A 37.4 . . ?
C13 Cl3 H12A 55.8 . . ?
Cl5 Cl4 Cl6 12.1(9) . . ?
Cl5 Cl4 C13 96.4(11) . . ?
Cl6 Cl4 C13 88.0(10) . . ?
Cl5 Cl4 C12 75.6(11) . . ?
Cl6 Cl4 C12 66.9(10) . . ?
C13 Cl4 C12 21.1(7) . . ?
Cl5 Cl4 H13A 138.7 . . ?
Cl6 Cl4 H13A 128.6 . . ?
C13 Cl4 H13A 42.9 . . ?
C12 Cl4 H13A 63.3 . . ?
Cl4 Cl5 C12 71.5(11) . . ?
Cl4 Cl5 C13 50.2(9) . . ?
C12 Cl5 C13 21.5(6) . . ?
Cl4 Cl6 C12 67.2(8) . . ?
Cl4 Cl6 C13 46.8(6) . . ?
C12 Cl6 C13 20.4(6) . . ?
C13 C12 Cl3 113(3) . . ?
C13 C12 C11 80(2) . . ?
Cl3 C12 C11 118.0(13) . . ?
C13 C12 Cl6 95(3) . . ?
Cl3 C12 Cl6 116.8(12) . . ?
C11 C12 Cl6 122.6(11) . . ?
C13 C12 Cl4 49(2) . . ?
Cl3 C12 Cl4 128.2(14) . . ?
C11 C12 Cl4 105.9(11) . . ?
Cl6 C12 Cl4 46.0(9) . . ?
C13 C12 Cl2 93(2) . . ?
Cl3 C12 Cl2 19.7(6) . . ?
C11 C12 Cl2 119.1(11) . . ?
Cl6 C12 Cl2 118.3(11) . . ?
Cl4 C12 Cl2 113.5(12) . . ?
C13 C12 Cl5 81(2) . . ?
Cl3 C12 Cl5 126.9(13) . . ?
C11 C12 Cl5 114.8(10) . . ?
Cl6 C12 Cl5 14.2(7) . . ?
Cl4 C12 Cl5 32.9(7) . . ?
Cl2 C12 Cl5 123.7(11) . . ?
C13 C12 Cl1 81(2) . . ?
Cl3 C12 Cl1 32.9(13) . . ?
C11 C12 Cl1 123.5(14) . . ?
Cl6 C12 Cl1 111.6(13) . . ?
Cl4 C12 Cl1 99.9(15) . . ?
Cl2 C12 Cl1 14.0(10) . . ?
Cl5 C12 Cl1 114.1(14) . . ?
C13 C12 H12A 171.6 . . ?
Cl3 C12 H12A 75.6 . . ?
C11 C12 H12A 95.1 . . ?
Cl6 C12 H12A 82.6 . . ?
Cl4 C12 H12A 128.0 . . ?
Cl2 C12 H12A 95.2 . . ?
Cl5 C12 H12A 95.1 . . ?
Cl1 C12 H12A 107.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.7(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C2 C1 C6 C7 -179.2(2) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C4 C5 C6 C7 -179.7(2) . . . . ?
C8 N1 C7 C6 -178.89(18) . . . . ?
C1 C6 C7 N1 -82.6(3) . . . . ?
C5 C6 C7 N1 98.1(2) . . . . ?
C7 N1 C8 C10 64.6(3) . . . . ?
C7 N1 C8 C9 -170.7(2) . . . . ?
O1 C11 C13 C12 -102(2) . . . . ?
O2 C11 C13 C12 89(2) . . . . ?
O1 C11 C13 Cl4 152.7(10) . . . . ?
O2 C11 C13 Cl4 -16.9(11) . . . . ?
C12 C11 C13 Cl4 -106(3) . . . . ?
O1 C11 C13 Cl1 -36.0(11) . . . . ?
O2 C11 C13 Cl1 154.4(11) . . . . ?
C12 C11 C13 Cl1 66(2) . . . . ?
O1 C11 C13 Cl5 -171.5(4) . . . . ?
O2 C11 C13 Cl5 18.9(6) . . . . ?
C12 C11 C13 Cl5 -70(2) . . . . ?
O1 C11 C13 Cl2 -43.4(4) . . . . ?
O2 C11 C13 Cl2 147.0(3) . . . . ?
C12 C11 C13 Cl2 58(2) . . . . ?
O1 C11 C13 Cl6 -157.4(5) . . . . ?
O2 C11 C13 Cl6 33.0(6) . . . . ?
C12 C11 C13 Cl6 -56(2) . . . . ?
O1 C11 C13 Cl3 -58.3(5) . . . . ?
O2 C11 C13 Cl3 132.1(5) . . . . ?
C12 C11 C13 Cl3 43(2) . . . . ?
Cl3 Cl2 C13 C12 7(3) . . . . ?
Cl3 Cl2 C13 Cl4 106.4(19) . . . . ?
C12 Cl2 C13 Cl4 99(3) . . . . ?
Cl3 Cl2 C13 C11 -57.6(16) . . . . ?
C12 Cl2 C13 C11 -65(2) . . . . ?
Cl3 Cl2 C13 Cl1 152(5) . . . . ?
C12 Cl2 C13 Cl1 145(5) . . . . ?
Cl3 Cl2 C13 Cl5 69.7(17) . . . . ?
C12 Cl2 C13 Cl5 63(2) . . . . ?
Cl3 Cl2 C13 Cl6 61.8(17) . . . . ?
C12 Cl2 C13 Cl6 55(2) . . . . ?
C12 Cl2 C13 Cl3 -7(3) . . . . ?
C12 C13 Cl1 Cl3 16(3) . . . . ?
Cl4 C13 Cl1 Cl3 122.6(18) . . . . ?
C11 C13 Cl1 Cl3 -50(2) . . . . ?
Cl5 C13 Cl1 Cl3 86.3(18) . . . . ?
Cl2 C13 Cl1 Cl3 -17(3) . . . . ?
Cl6 C13 Cl1 Cl3 76.1(18) . . . . ?
Cl4 C13 Cl1 C12 107(3) . . . . ?
C11 C13 Cl1 C12 -66(2) . . . . ?
Cl5 C13 Cl1 C12 70(2) . . . . ?
Cl2 C13 Cl1 C12 -33(5) . . . . ?
Cl6 C13 Cl1 C12 60(2) . . . . ?
Cl3 C13 Cl1 C12 -16(3) . . . . ?
C12 Cl2 Cl3 Cl1 -43(7) . . . . ?
C13 Cl2 Cl3 Cl1 -46(7) . . . . ?
C13 Cl2 Cl3 C12 -2.7(11) . . . . ?
C12 Cl2 Cl3 C13 2.7(11) . . . . ?
C12 Cl1 Cl3 Cl2 137(7) . . . . ?
C13 Cl1 Cl3 Cl2 130(7) . . . . ?
C13 Cl1 Cl3 C12 -6.5(11) . . . . ?
C12 Cl1 Cl3 C13 6.5(11) . . . . ?
C12 C13 Cl3 Cl2 -171(4) . . . . ?
Cl4 C13 Cl3 Cl2 -85.9(19) . . . . ?
C11 C13 Cl3 Cl2 126.2(16) . . . . ?
Cl1 C13 Cl3 Cl2 -12(2) . . . . ?
Cl5 C13 Cl3 Cl2 -116.3(16) . . . . ?
Cl6 C13 Cl3 Cl2 -120.6(16) . . . . ?
C12 C13 Cl3 Cl1 -159(4) . . . . ?
Cl4 C13 Cl3 Cl1 -74(2) . . . . ?
C11 C13 Cl3 Cl1 138.5(18) . . . . ?
Cl5 C13 Cl3 Cl1 -104.1(18) . . . . ?
Cl2 C13 Cl3 Cl1 12(2) . . . . ?
Cl6 C13 Cl3 Cl1 -108.4(19) . . . . ?
Cl4 C13 Cl3 C12 85(3) . . . . ?
C11 C13 Cl3 C12 -62(3) . . . . ?
Cl1 C13 Cl3 C12 159(4) . . . . ?
Cl5 C13 Cl3 C12 55(3) . . . . ?
Cl2 C13 Cl3 C12 171(4) . . . . ?
Cl6 C13 Cl3 C12 51(3) . . . . ?
C12 C13 Cl4 Cl5 -8(3) . . . . ?
C11 C13 Cl4 Cl5 78.9(13) . . . . ?
Cl1 C13 Cl4 Cl5 -92.8(16) . . . . ?
Cl2 C13 Cl4 Cl5 -82.7(14) . . . . ?
Cl6 C13 Cl4 Cl5 -8.6(9) . . . . ?
Cl3 C13 Cl4 Cl5 -61.6(16) . . . . ?
C12 C13 Cl4 Cl6 0(3) . . . . ?
C11 C13 Cl4 Cl6 87.6(10) . . . . ?
Cl1 C13 Cl4 Cl6 -84.2(14) . . . . ?
Cl5 C13 Cl4 Cl6 8.6(9) . . . . ?
Cl2 C13 Cl4 Cl6 -74.1(12) . . . . ?
Cl3 C13 Cl4 Cl6 -53.0(14) . . . . ?
C11 C13 Cl4 C12 87(3) . . . . ?
Cl1 C13 Cl4 C12 -84(3) . . . . ?
Cl5 C13 Cl4 C12 8(3) . . . . ?
Cl2 C13 Cl4 C12 -74(3) . . . . ?
Cl6 C13 Cl4 C12 0(3) . . . . ?
Cl3 C13 Cl4 C12 -53(2) . . . . ?
Cl6 Cl4 Cl5 C12 -43(4) . . . . ?
C13 Cl4 Cl5 C12 3.1(11) . . . . ?
Cl6 Cl4 Cl5 C13 -46(4) . . . . ?
C12 Cl4 Cl5 C13 -3.1(11) . . . . ?
C12 C13 Cl5 Cl4 172(3) . . . . ?
C11 C13 Cl5 Cl4 -118.7(14) . . . . ?
Cl1 C13 Cl5 Cl4 101.7(16) . . . . ?
Cl2 C13 Cl5 Cl4 115.5(13) . . . . ?
Cl6 C13 Cl5 Cl4 152(3) . . . . ?
Cl3 C13 Cl5 Cl4 132.6(14) . . . . ?
Cl4 C13 Cl5 C12 -172(3) . . . . ?
C11 C13 Cl5 C12 69(2) . . . . ?
Cl1 C13 Cl5 C12 -70(2) . . . . ?
Cl2 C13 Cl5 C12 -56(2) . . . . ?
Cl6 C13 Cl5 C12 -20(3) . . . . ?
Cl3 C13 Cl5 C12 -39(2) . . . . ?
Cl5 Cl4 Cl6 C12 135(4) . . . . ?
C13 Cl4 Cl6 C12 -0.1(11) . . . . ?
Cl5 Cl4 Cl6 C13 135(4) . . . . ?
C12 Cl4 Cl6 C13 0.1(11) . . . . ?
C12 C13 Cl6 Cl4 -180(3) . . . . ?
C11 C13 Cl6 Cl4 -117.3(11) . . . . ?
Cl1 C13 Cl6 Cl4 111.5(14) . . . . ?
Cl5 C13 Cl6 Cl4 -21(3) . . . . ?
Cl2 C13 Cl6 Cl4 124.7(11) . . . . ?
Cl3 C13 Cl6 Cl4 140.1(12) . . . . ?
Cl4 C13 Cl6 C12 180(3) . . . . ?
C11 C13 Cl6 C12 62(2) . . . . ?
Cl1 C13 Cl6 C12 -69(2) . . . . ?
Cl5 C13 Cl6 C12 158(4) . . . . ?
Cl2 C13 Cl6 C12 -56(2) . . . . ?
Cl3 C13 Cl6 C12 -40(2) . . . . ?
Cl4 C13 C12 Cl3 -121.8(18) . . . . ?
C11 C13 C12 Cl3 116(2) . . . . ?
Cl1 C13 C12 Cl3 -10.4(18) . . . . ?
Cl5 C13 C12 Cl3 -126(2) . . . . ?
Cl2 C13 C12 Cl3 -2.8(12) . . . . ?
Cl6 C13 C12 Cl3 -122(2) . . . . ?
Cl4 C13 C12 C11 122.1(13) . . . . ?
Cl1 C13 C12 C11 -126.5(10) . . . . ?
Cl5 C13 C12 C11 117.4(5) . . . . ?
Cl2 C13 C12 C11 -119.0(10) . . . . ?
Cl6 C13 C12 C11 122.3(10) . . . . ?
Cl3 C13 C12 C11 -116(2) . . . . ?
Cl4 C13 C12 Cl6 0(2) . . . . ?
C11 C13 C12 Cl6 -122.3(10) . . . . ?
Cl1 C13 C12 Cl6 111.2(13) . . . . ?
Cl5 C13 C12 Cl6 -4.9(8) . . . . ?
Cl2 C13 C12 Cl6 118.7(14) . . . . ?
Cl3 C13 C12 Cl6 122(2) . . . . ?
C11 C13 C12 Cl4 -122.1(13) . . . . ?
Cl1 C13 C12 Cl4 111.4(16) . . . . ?
Cl5 C13 C12 Cl4 -4.7(16) . . . . ?
Cl2 C13 C12 Cl4 118.9(13) . . . . ?
Cl6 C13 C12 Cl4 0(2) . . . . ?
Cl3 C13 C12 Cl4 121.8(18) . . . . ?
Cl4 C13 C12 Cl2 -118.9(13) . . . . ?
C11 C13 C12 Cl2 119.0(10) . . . . ?
Cl1 C13 C12 Cl2 -7.5(11) . . . . ?
Cl5 C13 C12 Cl2 -123.6(10) . . . . ?
Cl6 C13 C12 Cl2 -118.7(14) . . . . ?
Cl3 C13 C12 Cl2 2.8(12) . . . . ?
Cl4 C13 C12 Cl5 4.7(16) . . . . ?
C11 C13 C12 Cl5 -117.4(5) . . . . ?
Cl1 C13 C12 Cl5 116.1(10) . . . . ?
Cl2 C13 C12 Cl5 123.6(10) . . . . ?
Cl6 C13 C12 Cl5 4.9(8) . . . . ?
Cl3 C13 C12 Cl5 126(2) . . . . ?
Cl4 C13 C12 Cl1 -111.4(16) . . . . ?
C11 C13 C12 Cl1 126.5(10) . . . . ?
Cl5 C13 C12 Cl1 -116.1(10) . . . . ?
Cl2 C13 C12 Cl1 7.5(11) . . . . ?
Cl6 C13 C12 Cl1 -111.2(13) . . . . ?
Cl3 C13 C12 Cl1 10.4(18) . . . . ?
Cl2 Cl3 C12 C13 8(3) . . . . ?
Cl1 Cl3 C12 C13 19(3) . . . . ?
Cl2 Cl3 C12 C11 98.5(19) . . . . ?
Cl1 Cl3 C12 C11 109(2) . . . . ?
C13 Cl3 C12 C11 90(3) . . . . ?
Cl2 Cl3 C12 Cl6 -100(2) . . . . ?
Cl1 Cl3 C12 Cl6 -89(2) . . . . ?
C13 Cl3 C12 Cl6 -108(3) . . . . ?
Cl2 Cl3 C12 Cl4 -46(3) . . . . ?
Cl1 Cl3 C12 Cl4 -35(2) . . . . ?
C13 Cl3 C12 Cl4 -54(3) . . . . ?
Cl1 Cl3 C12 Cl2 11(2) . . . . ?
C13 Cl3 C12 Cl2 -8(3) . . . . ?
Cl2 Cl3 C12 Cl5 -88(2) . . . . ?
Cl1 Cl3 C12 Cl5 -77(2) . . . . ?
C13 Cl3 C12 Cl5 -96(3) . . . . ?
Cl2 Cl3 C12 Cl1 -11(2) . . . . ?
C13 Cl3 C12 Cl1 -19(3) . . . . ?
O1 C11 C12 C13 90(2) . . . . ?
O2 C11 C12 C13 -103(2) . . . . ?
O1 C11 C12 Cl3 -20.0(15) . . . . ?
O2 C11 C12 Cl3 146.6(10) . . . . ?
C13 C11 C12 Cl3 -110(3) . . . . ?
O1 C11 C12 Cl6 179.2(9) . . . . ?
O2 C11 C12 Cl6 -14.3(15) . . . . ?
C13 C11 C12 Cl6 89(3) . . . . ?
O1 C11 C12 Cl4 131.7(9) . . . . ?
O2 C11 C12 Cl4 -61.7(13) . . . . ?
C13 C11 C12 Cl4 41.4(18) . . . . ?
O1 C11 C12 Cl2 2.4(14) . . . . ?
O2 C11 C12 Cl2 169.0(8) . . . . ?
C13 C11 C12 Cl2 -88(2) . . . . ?
O1 C11 C12 Cl5 165.6(8) . . . . ?
O2 C11 C12 Cl5 -27.8(13) . . . . ?
C13 C11 C12 Cl5 75(2) . . . . ?
O1 C11 C12 Cl1 18.0(19) . . . . ?
O2 C11 C12 Cl1 -175.4(15) . . . . ?
C13 C11 C12 Cl1 -72(2) . . . . ?
Cl4 Cl6 C12 C13 0(2) . . . . ?
Cl4 Cl6 C12 Cl3 118.5(16) . . . . ?
C13 Cl6 C12 Cl3 118(3) . . . . ?
Cl4 Cl6 C12 C11 -80.4(14) . . . . ?
C13 Cl6 C12 C11 -81(2) . . . . ?
C13 Cl6 C12 Cl4 0(2) . . . . ?
Cl4 Cl6 C12 Cl2 96.3(14) . . . . ?
C13 Cl6 C12 Cl2 96(3) . . . . ?
Cl4 Cl6 C12 Cl5 -20(2) . . . . ?
C13 Cl6 C12 Cl5 -20(3) . . . . ?
Cl4 Cl6 C12 Cl1 82.7(17) . . . . ?
C13 Cl6 C12 Cl1 82(3) . . . . ?
Cl5 Cl4 C12 C13 171(3) . . . . ?
Cl6 Cl4 C12 C13 -180(3) . . . . ?
Cl5 Cl4 C12 Cl3 -100.9(18) . . . . ?
Cl6 Cl4 C12 Cl3 -92.1(17) . . . . ?
C13 Cl4 C12 Cl3 88(3) . . . . ?
Cl5 Cl4 C12 C11 111.3(13) . . . . ?
Cl6 Cl4 C12 C11 120.2(12) . . . . ?
C13 Cl4 C12 C11 -60(2) . . . . ?
Cl5 Cl4 C12 Cl6 -8.9(9) . . . . ?
C13 Cl4 C12 Cl6 180(3) . . . . ?
Cl5 Cl4 C12 Cl2 -116.2(13) . . . . ?
Cl6 Cl4 C12 Cl2 -107.4(12) . . . . ?
C13 Cl4 C12 Cl2 72(2) . . . . ?
Cl6 Cl4 C12 Cl5 8.9(9) . . . . ?
C13 Cl4 C12 Cl5 -171(3) . . . . ?
Cl5 Cl4 C12 Cl1 -119.5(15) . . . . ?
Cl6 Cl4 C12 Cl1 -110.6(14) . . . . ?
C13 Cl4 C12 Cl1 69(3) . . . . ?
Cl3 Cl2 C12 C13 -172(3) . . . . ?
C13 Cl2 C12 Cl3 172(3) . . . . ?
Cl3 Cl2 C12 C11 -92(2) . . . . ?
C13 Cl2 C12 C11 80(2) . . . . ?
Cl3 Cl2 C12 Cl6 91(2) . . . . ?
C13 Cl2 C12 Cl6 -97(3) . . . . ?
Cl3 Cl2 C12 Cl4 142(2) . . . . ?
C13 Cl2 C12 Cl4 -46(2) . . . . ?
Cl3 Cl2 C12 Cl5 106(2) . . . . ?
C13 Cl2 C12 Cl5 -82(3) . . . . ?
Cl3 Cl2 C12 Cl1 156(5) . . . . ?
C13 Cl2 C12 Cl1 -32(5) . . . . ?
Cl4 Cl5 C12 C13 -7(2) . . . . ?
Cl4 Cl5 C12 Cl3 105.3(18) . . . . ?
C13 Cl5 C12 Cl3 112(3) . . . . ?
Cl4 Cl5 C12 C11 -80.8(15) . . . . ?
C13 Cl5 C12 C11 -74(2) . . . . ?
Cl4 Cl5 C12 Cl6 153(3) . . . . ?
C13 Cl5 C12 Cl6 160(3) . . . . ?
C13 Cl5 C12 Cl4 7(2) . . . . ?
Cl4 Cl5 C12 Cl2 81.5(15) . . . . ?
C13 Cl5 C12 Cl2 88(3) . . . . ?
Cl4 Cl5 C12 Cl1 69.9(17) . . . . ?
C13 Cl5 C12 Cl1 76(3) . . . . ?
Cl3 Cl1 C12 C13 -162(3) . . . . ?
C13 Cl1 C12 Cl3 162(3) . . . . ?
Cl3 Cl1 C12 C11 -91(2) . . . . ?
C13 Cl1 C12 C11 71(2) . . . . ?
Cl3 Cl1 C12 Cl6 106.2(19) . . . . ?
C13 Cl1 C12 Cl6 -92(3) . . . . ?
Cl3 Cl1 C12 Cl4 152.6(18) . . . . ?
C13 Cl1 C12 Cl4 -45(2) . . . . ?
Cl3 Cl1 C12 Cl2 -15(3) . . . . ?
C13 Cl1 C12 Cl2 147(5) . . . . ?
Cl3 Cl1 C12 Cl5 121.4(18) . . . . ?
C13 Cl1 C12 Cl5 -76(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 987647'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_N-IPBADC-356K

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'N-Isopropylbenzylammonium Dichloroacetate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 N, C2 H Cl2 O2'
_chemical_formula_sum            'C12 H17 Cl2 N O2'
_chemical_formula_weight         278.17

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   9.7987(7)
_cell_length_b                   8.6320(4)
_cell_length_c                   17.8455(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.919(7)
_cell_angle_gamma                90.00
_cell_volume                     1444.08(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    356(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      356(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9116
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2957
_reflns_number_gt                1877
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1652P)²+0.5993P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2957
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0889
_refine_ls_wR_factor_ref         0.3091
_refine_ls_wR_factor_gt          0.2759
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.005

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.62519(18) 0.83562(16) 0.01312(9) 0.1285(7) Uani 1 1 d . . .
Cl1 Cl 0.69226(18) 0.51578(18) -0.00746(9) 0.1257(7) Uani 1 1 d . . .
N1 N 0.9452(3) 1.2577(3) 0.19729(17) 0.0628(8) Uani 1 1 d . . .
H1A H 0.9197 1.3533 0.1749 0.075 Uiso 1 1 calc R . .
H1B H 0.9984 1.2737 0.2484 0.075 Uiso 1 1 calc R . .
O2 O 0.8731(4) 0.8109(3) 0.1492(2) 0.0993(11) Uani 1 1 d . . .
C11 C 0.8372(4) 0.6817(4) 0.1234(2) 0.0716(10) Uani 1 1 d . . .
O1 O 0.8980(4) 0.5602(3) 0.1479(2) 0.1001(11) Uani 1 1 d . . .
C6 C 0.7265(4) 1.2616(4) 0.2398(2) 0.0664(9) Uani 1 1 d . . .
C7 C 0.8128(5) 1.1725(4) 0.1973(3) 0.0830(12) Uani 1 1 d . . .
H7A H 0.7545 1.1542 0.1426 0.100 Uiso 1 1 calc R . .
H7B H 0.8388 1.0705 0.2228 0.100 Uiso 1 1 calc R . .
C8 C 1.0374(5) 1.1786(4) 0.1550(3) 0.0785(11) Uani 1 1 d . . .
H8 H 1.0581 1.0713 0.1764 0.094 Uiso 1 1 calc R . .
C12 C 0.6934(5) 0.6653(5) 0.0608(3) 0.0914(13) Uani 1 1 d . . .
H12 H 0.6242 0.6321 0.0893 0.110 Uiso 1 1 calc R . .
C5 C 0.7569(5) 1.2560(5) 0.3200(3) 0.0853(12) Uani 1 1 d . . .
H5 H 0.8344 1.1949 0.3498 0.102 Uiso 1 1 calc R . .
C1 C 0.6119(4) 1.3503(5) 0.1977(3) 0.0835(12) Uani 1 1 d . . .
H1 H 0.5886 1.3556 0.1423 0.100 Uiso 1 1 calc R . .
C4 C 0.6761(6) 1.3381(6) 0.3573(3) 0.0993(15) Uani 1 1 d . . .
H4 H 0.6986 1.3345 0.4127 0.119 Uiso 1 1 calc R . .
C2 C 0.5318(5) 1.4309(6) 0.2366(3) 0.1016(15) Uani 1 1 d . . .
H2 H 0.4530 1.4914 0.2077 0.122 Uiso 1 1 calc R . .
C10 C 1.1763(6) 1.2655(7) 0.1721(4) 0.1057(16) Uani 1 1 d . . .
H10A H 1.1589 1.3692 0.1489 0.158 Uiso 1 1 calc R . .
H10B H 1.2421 1.2093 0.1497 0.158 Uiso 1 1 calc R . .
H10C H 1.2184 1.2746 0.2289 0.158 Uiso 1 1 calc R . .
C9 C 0.9604(7) 1.1669(7) 0.0685(4) 0.1153(18) Uani 1 1 d . . .
H9A H 0.8810 1.0936 0.0604 0.173 Uiso 1 1 calc R . .
H9B H 1.0267 1.1306 0.0405 0.173 Uiso 1 1 calc R . .
H9C H 0.9233 1.2691 0.0485 0.173 Uiso 1 1 calc R . .
C3 C 0.5639(6) 1.4248(7) 0.3152(4) 0.1044(15) Uani 1 1 d . . .
H3 H 0.5080 1.4811 0.3413 0.125 Uiso 1 1 calc R . .


_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
Cl2 C12 1.732(4) . ?
Cl1 C12 1.772(5) . ?
N1 C8 1.500(5) . ?
N1 C7 1.491(5) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
O2 C11 1.219(4) . ?
C11 O1 1.222(4) . ?
C11 C12 1.529(6) . ?
C6 C5 1.376(6) . ?
C6 C1 1.385(5) . ?
C6 C7 1.501(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.511(8) . ?
C8 C10 1.505(7) . ?
C8 H8 1.0000 . ?
C12 H12 1.0000 . ?
C5 C4 1.369(7) . ?
C5 H5 0.9500 . ?
C1 C2 1.378(7) . ?
C1 H1 0.9500 . ?
C4 C3 1.361(8) . ?
C4 H4 0.9500 . ?
C2 C3 1.345(7) . ?
C2 H2 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C7 115.3(3) . . ?
C8 N1 H1A 108.4 . . ?
C7 N1 H1A 108.4 . . ?
C8 N1 H1B 108.4 . . ?
C7 N1 H1B 108.4 . . ?
H1A N1 H1B 107.5 . . ?
O2 C11 O1 126.3(4) . . ?
O2 C11 C12 117.7(3) . . ?
O1 C11 C12 115.6(3) . . ?
C5 C6 C1 118.6(4) . . ?
C5 C6 C7 121.6(4) . . ?
C1 C6 C7 119.8(4) . . ?
C6 C7 N1 111.5(3) . . ?
C6 C7 H7A 109.3 . . ?
N1 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
N1 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 C9 110.4(4) . . ?
N1 C8 C10 108.2(3) . . ?
C9 C8 C10 113.2(4) . . ?
N1 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C10 C8 H8 108.3 . . ?
C11 C12 Cl2 115.0(3) . . ?
C11 C12 Cl1 112.9(3) . . ?
Cl2 C12 Cl1 110.9(3) . . ?
C11 C12 H12 105.7 . . ?
Cl2 C12 H12 105.7 . . ?
Cl1 C12 H12 105.7 . . ?
C6 C5 C4 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C2 C1 C6 119.8(4) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C4 C5 120.3(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C3 C4 120.2(5) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C6 C7 N1 -82.8(5) . . . . ?
C1 C6 C7 N1 98.1(4) . . . . ?
C8 N1 C7 C6 -179.0(3) . . . . ?
C7 N1 C8 C9 65.0(5) . . . . ?
C7 N1 C8 C10 -170.6(4) . . . . ?
O2 C11 C12 Cl2 19.0(6) . . . . ?
O1 C11 C12 Cl2 -168.0(4) . . . . ?
O2 C11 C12 Cl1 147.6(4) . . . . ?
O1 C11 C12 Cl1 -39.3(6) . . . . ?
C1 C6 C5 C4 -0.7(6) . . . . ?
C7 C6 C5 C4 -179.8(4) . . . . ?
C5 C6 C1 C2 0.3(6) . . . . ?
C7 C6 C1 C2 179.4(4) . . . . ?
C6 C5 C4 C3 0.7(7) . . . . ?
C6 C1 C2 C3 0.2(7) . . . . ?
C1 C2 C3 C4 -0.2(8) . . . . ?
C5 C4 C3 C2 -0.2(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.075
_database_code_depnum_ccdc_archive 'CCDC 987648'
