# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'Dario Braga'
'Ulrich Baisch'
'Katia Rubini'

_publ_contact_author_name        'Dario Braga'
_publ_contact_author_email       DARIO.BRAGA@UNIBO.IT

_publ_section_title              
;
Remarkable structural similarities between organic
co-crystals and a metal-organic coordination network - insights into
hydrogen bonded aliphatic ammonium chlorides
;

# Attachment 'Piperazinium_dichloride_hemihyrate.cif'

data_ub043n_2
_database_code_depnum_ccdc_archive 'CCDC 696300'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'dipiperazinium tetrachloride monohydrate'
;
_chemical_name_common            
;
'dipiperazinium tetrachloride monohydrate'
;
_chemical_formula_moiety         '2(C4 H12 N2), H2 O, 4(Cl)'
_chemical_formula_sum            'C8 H26 Cl4 N4 O'
_chemical_formula_weight         336.13

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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_space_group_name_H-M   'P n m a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'

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

_cell_length_a                   11.6011(11)
_cell_length_b                   9.6530(8)
_cell_length_c                   13.9669(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1564.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200
_cell_measurement_reflns_used    1765
_cell_measurement_theta_min      2.5447
_cell_measurement_theta_max      28.8855
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3508
_exptl_crystal_size_mid          0.0787
_exptl_crystal_size_min          0.0329
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_measurement_device_type  xcalibur
_diffrn_measurement_device       '95mm CCD camera (sapphire) on κ-goniostat'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            5299
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_sigmaI/netI    0.0867
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         29.02
_diffrn_orient_matrix_UB_11      -0.0230008026
_diffrn_orient_matrix_UB_12      0.0263551432
_diffrn_orient_matrix_UB_13      -0.0428590105
_diffrn_orient_matrix_UB_21      -0.0202155303
_diffrn_orient_matrix_UB_22      -0.0546054986
_diffrn_orient_matrix_UB_23      -0.0179236353
_diffrn_orient_matrix_UB_31      -0.0662360849
_diffrn_orient_matrix_UB_32      0.0075368397
_diffrn_orient_matrix_UB_33      0.0202805561
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -41.00 53.80 1.2000 130.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.4392 45.0000 30.0000 0.0000 0.0000 79

#__ type_ start__ end____ width___ exp.time_
2 omega -88.00 -35.20 1.2000 130.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.4392 -77.0000 270.0000 0.0000 0.0000 44

#__ type_ start__ end____ width___ exp.time_
3 omega 11.00 42.20 1.2000 130.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 -45.0000 30.0000 0.0000 0.0000 26

;

_reflns_number_total             1916
_reflns_number_gt                1160
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0419P)²+0.0000P] 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_number_reflns         1916
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_restrained_S_all      0.888
_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 0.63194(8) 0.2500 0.61447(6) 0.0270(2) Uani 1 2 d S . .
Cl2 Cl 0.03684(8) 0.2500 0.35063(7) 0.0280(2) Uani 1 2 d S . .
N21 N -0.1364(3) 0.2500 0.7304(2) 0.0232(7) Uani 1 2 d S . .
N22 N 0.0176(3) 0.2500 0.5711(3) 0.0264(8) Uani 1 2 d S . .
N11 N 0.3224(3) 0.2500 0.2805(2) 0.0276(8) Uani 1 2 d S . .
N12 N 0.4274(3) 0.2500 0.4641(2) 0.0271(8) Uani 1 2 d S . .
C11 C 0.4267(2) 0.1230(3) 0.4047(2) 0.0286(7) Uani 1 1 d . . .
C12 C 0.3233(2) 0.1232(3) 0.3401(2) 0.0285(7) Uani 1 1 d . . .
C21 C -0.0705(3) 0.1243(3) 0.70460(19) 0.0232(6) Uani 1 1 d . . .
C22 C -0.0453(3) 0.1217(3) 0.59935(19) 0.0272(6) Uani 1 1 d . . .
Cl3 Cl 0.24919(6) 0.06263(6) 0.59884(5) 0.0344(2) Uani 1 1 d . . .
O3 O 0.1837(3) 0.2500 0.1226(2) 0.0345(8) Uani 1 2 d S . .
H1 H -0.1123(19) 0.047(2) 0.7199(16) 0.014(7) Uiso 1 1 d . . .
H2 H 0.326(2) 0.049(3) 0.2968(17) 0.019(7) Uiso 1 1 d . . .
H3 H 0.007(2) 0.040(3) 0.5833(18) 0.027(7) Uiso 1 1 d . . .
H4 H 0.002(2) 0.122(3) 0.7399(18) 0.034(8) Uiso 1 1 d . . .
H5 H 0.024(3) 0.2500 0.514(3) 0.020(11) Uiso 1 2 d S . .
H6 H 0.427(2) 0.051(3) 0.4494(18) 0.025(7) Uiso 1 1 d . . .
H7 H 0.486(4) 0.2500 0.506(3) 0.036(12) Uiso 1 2 d S . .
H8 H -0.112(2) 0.119(3) 0.5588(19) 0.032(8) Uiso 1 1 d . . .
H9 H 0.251(2) 0.120(3) 0.3753(19) 0.037(8) Uiso 1 1 d . . .
H10 H -0.148(3) 0.2500 0.791(3) 0.038(12) Uiso 1 2 d S . .
H11 H -0.199(4) 0.2500 0.702(3) 0.040(13) Uiso 1 2 d S . .
H12 H 0.087(4) 0.2500 0.598(3) 0.037(13) Uiso 1 2 d S . .
H13 H 0.204(3) 0.181(3) 0.097(2) 0.050(10) Uiso 1 1 d . . .
H14 H 0.498(2) 0.117(3) 0.3669(18) 0.029(8) Uiso 1 1 d . . .
H16 H 0.378(4) 0.2500 0.238(3) 0.041(13) Uiso 1 2 d S . .
H21 H 0.370(4) 0.2500 0.503(3) 0.043(14) Uiso 1 2 d S . .
H23 H 0.262(4) 0.2500 0.243(3) 0.044(14) Uiso 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0274(5) 0.0294(5) 0.0241(5) 0.000 -0.0031(4) 0.000
Cl2 0.0294(5) 0.0319(5) 0.0226(5) 0.000 -0.0026(4) 0.000
N21 0.0205(19) 0.0327(19) 0.0165(17) 0.000 0.0010(15) 0.000
N22 0.028(2) 0.033(2) 0.018(2) 0.000 0.0030(16) 0.000
N11 0.0238(19) 0.041(2) 0.0185(16) 0.000 0.0000(16) 0.000
N12 0.024(2) 0.035(2) 0.0229(18) 0.000 -0.0077(17) 0.000
C11 0.0294(16) 0.0205(14) 0.0361(17) 0.0032(15) -0.0065(14) 0.0011(13)
C12 0.0252(16) 0.0227(15) 0.0375(17) -0.0097(15) -0.0035(14) -0.0026(14)
C21 0.0286(16) 0.0154(13) 0.0256(15) 0.0026(13) -0.0002(13) -0.0023(14)
C22 0.0322(16) 0.0233(15) 0.0262(15) -0.0034(14) 0.0001(14) -0.0024(14)
Cl3 0.0412(4) 0.0270(4) 0.0350(4) -0.0025(3) -0.0036(3) 0.0011(3)
O3 0.0375(18) 0.0337(19) 0.0322(17) 0.000 -0.0031(14) 0.000

_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
N21 C21 1.479(3) 7_565 ?
N21 C21 1.479(3) . ?
N21 H10 0.85(4) . ?
N21 H11 0.82(4) . ?
N22 C22 1.490(3) . ?
N22 C22 1.490(3) 7_565 ?
N22 H5 0.80(4) . ?
N22 H12 0.88(4) . ?
N11 C12 1.480(3) . ?
N11 C12 1.480(3) 7_565 ?
N11 H16 0.88(4) . ?
N11 H23 0.87(4) . ?
N12 C11 1.480(3) . ?
N12 C11 1.480(3) 7_565 ?
N12 H7 0.89(4) . ?
N12 H21 0.86(4) . ?
C11 C12 1.501(4) . ?
C11 H6 0.94(3) . ?
C11 H14 0.99(2) . ?
C12 H2 0.94(2) . ?
C12 H9 0.97(3) . ?
C21 C22 1.499(4) . ?
C21 H1 0.91(2) . ?
C21 H4 0.97(3) . ?
C22 H3 1.02(3) . ?
C22 H8 0.96(3) . ?
O3 H13 0.79(3) . ?

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
C21 N21 C21 110.3(3) 7_565 . ?
C21 N21 H10 108.8(13) 7_565 . ?
C21 N21 H10 108.8(13) . . ?
C21 N21 H11 109.7(14) 7_565 . ?
C21 N21 H11 109.7(14) . . ?
H10 N21 H11 109(4) . . ?
C22 N22 C22 112.4(3) . 7_565 ?
C22 N22 H5 108.0(13) . . ?
C22 N22 H5 108.0(13) 7_565 . ?
C22 N22 H12 109.4(12) . . ?
C22 N22 H12 109.4(12) 7_565 . ?
H5 N22 H12 110(4) . . ?
C12 N11 C12 111.6(3) . 7_565 ?
C12 N11 H16 112.1(12) . . ?
C12 N11 H16 112.1(12) 7_565 . ?
C12 N11 H23 109.9(13) . . ?
C12 N11 H23 109.9(13) 7_565 . ?
H16 N11 H23 101(3) . . ?
C11 N12 C11 111.9(3) . 7_565 ?
C11 N12 H7 111.7(12) . . ?
C11 N12 H7 111.7(12) 7_565 . ?
C11 N12 H21 110.5(14) . . ?
C11 N12 H21 110.5(13) 7_565 . ?
H7 N12 H21 100(4) . . ?
N12 C11 C12 109.9(3) . . ?
N12 C11 H6 104.0(16) . . ?
C12 C11 H6 113.9(16) . . ?
N12 C11 H14 110.0(16) . . ?
C12 C11 H14 110.6(15) . . ?
H6 C11 H14 108(2) . . ?
N11 C12 C11 110.2(3) . . ?
N11 C12 H2 105.5(14) . . ?
C11 C12 H2 111.1(15) . . ?
N11 C12 H9 107.6(17) . . ?
C11 C12 H9 112.5(16) . . ?
H2 C12 H9 110(2) . . ?
N21 C21 C22 110.7(2) . . ?
N21 C21 H1 109.8(14) . . ?
C22 C21 H1 108.6(14) . . ?
N21 C21 H4 109.7(16) . . ?
C22 C21 H4 109.1(15) . . ?
H1 C21 H4 109(2) . . ?
N22 C22 C21 110.0(2) . . ?
N22 C22 H3 107.0(14) . . ?
C21 C22 H3 110.2(14) . . ?
N22 C22 H8 105.1(16) . . ?
C21 C22 H8 115.1(15) . . ?
H3 C22 H8 109(2) . . ?

_diffrn_measured_fraction_theta_max 0.870
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.082

# Attachment 'Piperazinium_dichloride_monohyrate.cif'

data_043n_070308_5
_database_code_depnum_ccdc_archive 'CCDC 696301'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'piperazinium dichloride monohydrate'
;
_chemical_name_common            
;
'piperazinium dichloride monohydrate'
;
_chemical_formula_moiety         'C4 H12 N2, H2 O, 2(Cl)'
_chemical_formula_sum            'C4 H14 Cl2 N2 O'
_chemical_formula_weight         177.07

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   10.1916(3)
_cell_length_b                   6.3108(2)
_cell_length_c                   13.4929(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.553(3)
_cell_angle_gamma                90.00
_cell_volume                     827.42(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4590
_cell_measurement_theta_min      3.1489
_cell_measurement_theta_max      29.3412
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3074
_exptl_crystal_size_mid          0.2099
_exptl_crystal_size_min          0.0414
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376

_diffrn_measurement_device_type  xcalibur
_diffrn_measurement_device       '95mm CCD camera (sapphire) on κ-goniostat'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.1340

_diffrn_reflns_number            9549
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         29.47
_reflns_number_total             1052
_reflns_number_gt                787
_reflns_threshold_expression     >2sigma(I)
_diffrn_orient_matrix_UB_11      -0.0114045098
_diffrn_orient_matrix_UB_12      -0.0476975938
_diffrn_orient_matrix_UB_13      0.0442112230
_diffrn_orient_matrix_UB_21      -0.0592250400
_diffrn_orient_matrix_UB_22      0.0638485545
_diffrn_orient_matrix_UB_23      -0.0068199775
_diffrn_orient_matrix_UB_31      -0.0408613331
_diffrn_orient_matrix_UB_32      -0.0791183565
_diffrn_orient_matrix_UB_33      -0.0320767880
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -43.00 9.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5173 0.0000 330.0000 0.0000 0.0000 52

#__ type_ start__ end____ width___ exp.time_
2 omega -89.00 -39.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5173 -45.0000 30.0000 0.0000 0.0000 50

#__ type_ start__ end____ width___ exp.time_
3 omega 5.00 51.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5173 0.0000 240.0000 0.0000 0.0000 46

#__ type_ start__ end____ width___ exp.time_
4 omega -43.00 6.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5173 -45.0000 210.0000 0.0000 0.0000 49

#__ type_ start__ end____ width___ exp.time_
5 omega -89.00 6.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5173 -45.0000 120.0000 0.0000 0.0000 95

#__ type_ start__ end____ width___ exp.time_
6 omega -39.00 13.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5173 -77.0000 150.0000 0.0000 0.0000 52

#__ type_ start__ end____ width___ exp.time_
7 omega 5.00 55.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5173 0.0000 180.0000 0.0000 0.0000 50

#__ type_ start__ end____ width___ exp.time_
8 omega -43.00 6.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5173 -45.0000 270.0000 0.0000 0.0000 49

#__ type_ start__ end____ width___ exp.time_
9 omega 5.00 54.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5173 45.0000 0.0000 0.0000 0.0000 49

#__ type_ start__ end____ width___ exp.time_
10 omega -48.00 4.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5173 77.0000 210.0000 0.0000 0.0000 52

#__ type_ start__ end____ width___ exp.time_
11 omega 5.00 54.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5173 45.0000 60.0000 0.0000 0.0000 49

#__ type_ start__ end____ width___ exp.time_
12 omega -48.00 5.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5173 77.0000 120.0000 0.0000 0.0000 53

#__ type_ start__ end____ width___ exp.time_
13 omega -84.00 -43.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5173 -45.0000 240.0000 0.0000 0.0000 41

#__ type_ start__ end____ width___ exp.time_
14 omega 38.00 79.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 -129.0000 86.0000 0.0000 0.0000 41

#__ type_ start__ end____ width___ exp.time_
15 omega 38.00 78.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 -129.0000 357.0000 0.0000 0.0000 40

#__ type_ start__ end____ width___ exp.time_
16 omega -51.00 -17.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 -77.0000 180.0000 0.0000 0.0000 34

#__ type_ start__ end____ width___ exp.time_
17 omega -6.00 43.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 -45.0000 240.0000 0.0000 0.0000 49

#__ type_ start__ end____ width___ exp.time_
18 omega -11.00 41.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 77.0000 30.0000 0.0000 0.0000 52

#__ type_ start__ end____ width___ exp.time_
19 omega 14.00 60.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 -96.0000 36.0000 0.0000 0.0000 46

#__ type_ start__ end____ width___ exp.time_
20 omega 6.00 48.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 -87.0000 101.0000 0.0000 0.0000 42

#__ type_ start__ end____ width___ exp.time_
21 omega 20.00 64.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 -104.0000 237.0000 0.0000 0.0000 44

#__ type_ start__ end____ width___ exp.time_
22 omega -51.00 37.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 -77.0000 300.0000 0.0000 0.0000 88

#__ type_ start__ end____ width___ exp.time_
23 omega 13.00 38.00 1.0000 75.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 77.0000 90.0000 0.0000 0.0000 25

;
_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0514P)²+0.0000P] 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_number_reflns         1052
_refine_ls_number_parameters     69
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.79893(4) 0.09521(7) 0.66353(3) 0.04130(18) Uani 1 1 d . . .
N1 N 0.55067(15) 0.4117(2) 0.60227(10) 0.0310(3) Uani 1 1 d . . .
C1 C 0.62655(17) 0.5834(3) 0.56830(13) 0.0332(4) Uani 1 1 d . . .
C2 C 0.52860(17) 0.7184(3) 0.48735(13) 0.0340(4) Uani 1 1 d . . .
O1 O 1.0000 0.5439(4) 0.7500 0.0724(7) Uani 1 2 d S . .
H1A H 0.6932(19) 0.512(3) 0.5409(14) 0.037(5) Uiso 1 1 d . . .
H1B H 0.671(2) 0.670(3) 0.6315(15) 0.047(5) Uiso 1 1 d . . .
H2A H 0.461(2) 0.785(3) 0.5165(14) 0.040(5) Uiso 1 1 d . . .
H2B H 0.579(2) 0.838(3) 0.4653(15) 0.043(5) Uiso 1 1 d . . .
H1N H 0.496(2) 0.465(3) 0.6395(15) 0.042(5) Uiso 1 1 d . . .
H2N H 0.610(2) 0.329(4) 0.6475(15) 0.052(6) Uiso 1 1 d . . .
H1O H 1.064(2) 0.455(4) 0.7484(19) 0.063 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0371(3) 0.0517(3) 0.0342(3) 0.00147(18) 0.00949(17) 0.01658(19)
N1 0.0277(6) 0.0364(7) 0.0281(7) 0.0019(6) 0.0071(5) 0.0039(6)
C1 0.0264(7) 0.0383(9) 0.0323(8) -0.0044(7) 0.0050(6) -0.0039(7)
C2 0.0353(8) 0.0266(8) 0.0405(9) -0.0025(7) 0.0120(7) -0.0019(7)
O1 0.0549(14) 0.0557(14) 0.112(2) 0.000 0.0333(15) 0.000

_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 C1 1.482(2) . ?
N1 C2 1.483(2) 5_666 ?
N1 H1N 0.91(2) . ?
N1 H2N 0.89(2) . ?
C1 C2 1.503(2) . ?
C1 H1A 0.976(19) . ?
C1 H1B 1.00(2) . ?
C2 N1 1.483(2) 5_666 ?
C2 H2A 0.98(2) . ?
C2 H2B 1.01(2) . ?
O1 H1O 0.86(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 111.05(13) . 5_666 ?
C1 N1 H1N 111.1(13) . . ?
C2 N1 H1N 112.3(12) 5_666 . ?
C1 N1 H2N 109.6(14) . . ?
C2 N1 H2N 109.0(14) 5_666 . ?
H1N N1 H2N 103.6(17) . . ?
N1 C1 C2 110.20(13) . . ?
N1 C1 H1A 105.4(11) . . ?
C2 C1 H1A 111.9(11) . . ?
N1 C1 H1B 106.4(12) . . ?
C2 C1 H1B 109.9(12) . . ?
H1A C1 H1B 112.8(15) . . ?
N1 C2 C1 110.98(13) 5_666 . ?
N1 C2 H2A 106.8(11) 5_666 . ?
C1 C2 H2A 110.0(11) . . ?
N1 C2 H2B 112.0(11) 5_666 . ?
C1 C2 H2B 110.8(11) . . ?
H2A C2 H2B 106.1(15) . . ?

_diffrn_measured_fraction_theta_max 0.914
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.048

# Attachment 'dace_dichloride.cif'

data_043d_1
_database_code_depnum_ccdc_archive 'CCDC 696302'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'1,2-diammonio-cyclohexane dichloride'
;
_chemical_name_common            
;
'1,2-diammonio-cyclohexane dichloride'
;
_chemical_formula_moiety         'C6 H16 N2, 2(Cl)'
_chemical_formula_sum            'C6 H16 Cl2 N2'
_chemical_formula_weight         187.11

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   5.25760(10)
_cell_length_b                   14.8849(3)
_cell_length_c                   6.35470(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.850(2)
_cell_angle_gamma                90.00
_cell_volume                     489.981(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5192
_cell_measurement_theta_min      2.7266
_cell_measurement_theta_max      29.2953

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3190
_exptl_crystal_size_mid          0.2335
_exptl_crystal_size_min          0.0457
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             200
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_measurement_device_type  xcalibur
_diffrn_measurement_device       '95mm CCD camera (sapphire) on κ-goniostat'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            8998
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         29.39
_reflns_number_total             1208
_reflns_number_gt                993
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0456P)²+0.0071P] 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_number_reflns         1208
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0748
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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
Cl1 Cl 0.03190(6) 0.84579(2) 0.53709(5) 0.03928(14) Uani 1 1 d . . .
N1 N -0.5257(2) 0.84292(9) 0.2519(2) 0.0345(3) Uani 1 1 d . . .
H1N H -0.637(3) 0.8429(9) 0.324(3) 0.046(4) Uiso 1 1 d . . .
H2N H -0.527(3) 0.7940(11) 0.194(2) 0.037(4) Uiso 1 1 d . . .
H3N H -0.387(3) 0.8521(8) 0.335(3) 0.036(4) Uiso 1 1 d . . .
C1 C -0.5747(2) 0.91580(8) 0.09044(19) 0.0284(3) Uani 1 1 d . . .
H1 H -0.727(2) 0.9006(9) 0.000(2) 0.032(3) Uiso 1 1 d . . .
C2 C -0.3564(3) 0.91887(9) -0.0393(2) 0.0366(3) Uani 1 1 d . . .
H2A H -0.193(3) 0.9282(9) 0.067(2) 0.044(4) Uiso 1 1 d . . .
H2B H -0.352(3) 0.8626(10) -0.115(3) 0.044(4) Uiso 1 1 d . . .
C3 C -0.3977(3) 0.99521(8) -0.1998(2) 0.0337(3) Uani 1 1 d . . .
H3A H -0.263(3) 0.9974(8) -0.283(3) 0.044(4) Uiso 1 1 d . . .
H3B H -0.554(3) 0.9841(9) -0.301(3) 0.040(4) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0382(2) 0.0407(2) 0.0411(2) 0.00221(13) 0.01291(14) -0.00250(13)
N1 0.0361(6) 0.0344(6) 0.0354(6) 0.0003(5) 0.0129(5) 0.0000(5)
C1 0.0267(6) 0.0323(6) 0.0270(6) -0.0020(5) 0.0068(5) -0.0010(5)
C2 0.0409(7) 0.0342(7) 0.0395(7) 0.0003(5) 0.0206(6) 0.0069(5)
C3 0.0391(7) 0.0368(7) 0.0287(6) -0.0031(5) 0.0154(6) 0.0010(5)

_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 C1 1.4852(16) . ?
N1 H1N 0.802(18) . ?
N1 H2N 0.817(17) . ?
N1 H3N 0.835(16) . ?
C1 C3 1.5141(16) 3_475 ?
C1 C2 1.5243(16) . ?
C1 H1 0.932(14) . ?
C2 C3 1.5174(17) . ?
C2 H2A 1.005(15) . ?
C2 H2B 0.970(16) . ?
C3 C1 1.5142(16) 3_475 ?
C3 H3A 0.953(19) . ?
C3 H3B 0.967(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1N 109.6(11) . . ?
C1 N1 H2N 110.6(10) . . ?
H1N N1 H2N 107.8(14) . . ?
C1 N1 H3N 110.2(9) . . ?
H1N N1 H3N 106.7(16) . . ?
H2N N1 H3N 111.8(14) . . ?
N1 C1 C3 109.92(10) . 3_475 ?
N1 C1 C2 109.76(10) . . ?
C3 C1 C2 111.23(10) 3_475 . ?
N1 C1 H1 106.2(8) . . ?
C3 C1 H1 110.9(8) 3_475 . ?
C2 C1 H1 108.7(8) . . ?
C3 C2 C1 110.58(10) . . ?
C3 C2 H2A 110.8(8) . . ?
C1 C2 H2A 106.1(8) . . ?
C3 C2 H2B 109.0(9) . . ?
C1 C2 H2B 109.3(9) . . ?
H2A C2 H2B 111.2(13) . . ?
C1 C3 C2 111.13(11) 3_475 . ?
C1 C3 H3A 111.2(8) 3_475 . ?
C2 C3 H3A 111.3(8) . . ?
C1 C3 H3B 108.5(9) 3_475 . ?
C2 C3 H3B 109.0(8) . . ?
H3A C3 H3B 105.4(13) . . ?

_diffrn_measured_fraction_theta_max 0.892
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.042

# Attachment 'dace_dichloride_bisDMSO.cif'

data_ub043m_1
_database_code_depnum_ccdc_archive 'CCDC 696303'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'1,2-diammonio-cyclohexane dichloride mono-sulfoxide'
;
_chemical_name_common            
;
'1,2-diammonio-cyclohexane dichloride mono-sulfoxide'
;
_chemical_formula_moiety         'C6 H16 N2, 2(C2 H6 O S), 2(Cl)'
_chemical_formula_sum            'C10 H28 Cl2 N2 O2 S2'
_chemical_formula_weight         343.36

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8630(6)
_cell_length_b                   8.2478(9)
_cell_length_c                   9.5959(9)
_cell_angle_alpha                89.659(8)
_cell_angle_beta                 76.931(8)
_cell_angle_gamma                75.820(9)
_cell_volume                     437.64(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4109
_cell_measurement_theta_min      2.5502
_cell_measurement_theta_max      29.4046

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             184
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;

_diffrn_measurement_device_type  xcalibur
_diffrn_measurement_device       '95mm CCD camera (sapphire) on κ-goniostat'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            9199
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.5502
_diffrn_reflns_theta_max         29.4046
_diffrn_orient_matrix_UB_11      -0.0428873959
_diffrn_orient_matrix_UB_12      0.0879473189
_diffrn_orient_matrix_UB_13      0.0149608940
_diffrn_orient_matrix_UB_21      -0.0528181960
_diffrn_orient_matrix_UB_22      -0.0134870895
_diffrn_orient_matrix_UB_23      0.0721883971
_diffrn_orient_matrix_UB_31      0.1090401219
_diffrn_orient_matrix_UB_32      0.0015047110
_diffrn_orient_matrix_UB_33      0.0198551140
_reflns_number_total             2093
_reflns_number_gt                1483
_reflns_threshold_expression     >2sigma(I)

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -40.00 12.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5955 -77.0000 0.0000 0.0000 0.0000 52

#__ type_ start__ end____ width___ exp.time_
2 omega -86.00 -8.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5955 143.0000 -22.0000 0.0000 0.0000 78

#__ type_ start__ end____ width___ exp.time_
3 omega 5.00 55.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5955 0.0000 240.0000 0.0000 0.0000 50

#__ type_ start__ end____ width___ exp.time_
4 omega -48.00 5.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5955 77.0000 300.0000 0.0000 0.0000 53

#__ type_ start__ end____ width___ exp.time_
5 omega 5.00 55.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5955 0.0000 30.0000 0.0000 0.0000 50

#__ type_ start__ end____ width___ exp.time_
6 omega -41.00 9.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5955 45.0000 210.0000 0.0000 0.0000 50

#__ type_ start__ end____ width___ exp.time_
7 omega -88.00 12.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5955 -77.0000 210.0000 0.0000 0.0000 100

#__ type_ start__ end____ width___ exp.time_
8 omega -89.00 5.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5955 -45.0000 60.0000 0.0000 0.0000 94

#__ type_ start__ end____ width___ exp.time_
9 omega -79.00 -1.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5955 131.0000 78.0000 0.0000 0.0000 78

#__ type_ start__ end____ width___ exp.time_
10 omega -41.00 -15.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5955 45.0000 30.0000 0.0000 0.0000 26

#__ type_ start__ end____ width___ exp.time_
11 omega 1.00 53.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5955 77.0000 60.0000 0.0000 0.0000 52

#__ type_ start__ end____ width___ exp.time_
12 omega -48.00 -7.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5955 77.0000 270.0000 0.0000 0.0000 41

#__ type_ start__ end____ width___ exp.time_
13 omega -82.00 -39.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.5955 -45.0000 270.0000 0.0000 0.0000 43

#__ type_ start__ end____ width___ exp.time_
14 omega 0.00 80.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.3142 77.0000 330.0000 0.0000 0.0000 80

#__ type_ start__ end____ width___ exp.time_
15 omega 46.00 90.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.3142 45.0000 330.0000 0.0000 0.0000 44

#__ type_ start__ end____ width___ exp.time_
16 omega 58.00 88.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.3142 77.0000 60.0000 0.0000 0.0000 30

#__ type_ start__ end____ width___ exp.time_
17 omega -10.00 72.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.3142 -117.0000 333.0000 0.0000 0.0000 82

#__ type_ start__ end____ width___ exp.time_
18 omega 2.00 28.00 1.0000 13.9000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.3142 77.0000 30.0000 0.0000 0.0000 26

;
_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)+(0.0418P)²+0.0000P] 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_number_reflns         2093
_refine_ls_number_parameters     138
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0776
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      1.001
_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 0.21714(8) 0.98670(6) 0.16967(5) 0.04030(15) Uani 1 1 d . . .
N1 N 0.7972(3) 0.8247(2) 0.13855(19) 0.0335(4) Uani 1 1 d . . .
C1 C 0.9318(3) 0.6770(2) 0.03977(17) 0.0275(4) Uani 1 1 d . . .
C2 C 0.7575(3) 0.5949(2) -0.0095(2) 0.0335(4) Uani 1 1 d . . .
C3 C 1.1029(3) 0.5560(2) 0.11161(19) 0.0324(4) Uani 1 1 d . . .
H1N H 0.894(4) 0.888(2) 0.162(2) 0.049(6) Uiso 1 1 d . . .
H2N H 0.712(4) 0.800(3) 0.225(2) 0.050(6) Uiso 1 1 d . . .
H3N H 0.696(4) 0.890(3) 0.102(2) 0.043(6) Uiso 1 1 d . . .
H1 H 1.021(3) 0.720(2) -0.0390(18) 0.027(4) Uiso 1 1 d . . .
H2A H 0.662(3) 0.558(2) 0.0730(19) 0.030(4) Uiso 1 1 d . . .
H2B H 0.645(3) 0.675(2) -0.051(2) 0.040(5) Uiso 1 1 d . . .
H3A H 1.208(3) 0.615(2) 0.1430(18) 0.035(5) Uiso 1 1 d . . .
H3B H 1.005(3) 0.524(2) 0.1943(19) 0.033(5) Uiso 1 1 d . . .
S10 S 0.61941(8) 0.19164(6) 0.50071(5) 0.04162(15) Uani 1 1 d . . .
O10 O 0.4097(2) 0.30087(19) 0.60783(14) 0.0536(4) Uani 1 1 d . . .
C11 C 0.8717(4) 0.2742(4) 0.4980(3) 0.0592(7) Uani 1 1 d D . .
C12 C 0.5729(5) 0.2551(4) 0.3294(3) 0.0576(6) Uani 1 1 d . . .
H11A H 0.987(3) 0.228(3) 0.422(2) 0.068(7) Uiso 1 1 d D . .
H11B H 0.826(4) 0.390(3) 0.486(3) 0.067(8) Uiso 1 1 d . . .
H11C H 0.910(5) 0.252(3) 0.587(3) 0.096(9) Uiso 1 1 d . . .
H12A H 0.453(5) 0.210(3) 0.309(3) 0.079(8) Uiso 1 1 d . . .
H12B H 0.539(4) 0.378(3) 0.333(2) 0.069(8) Uiso 1 1 d . . .
H12C H 0.698(4) 0.209(3) 0.263(2) 0.065(7) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0329(2) 0.0426(3) 0.0469(3) 0.0080(2) -0.0112(2) -0.0104(2)
N1 0.0280(8) 0.0315(9) 0.0382(9) -0.0021(7) -0.0064(7) -0.0030(7)
C1 0.0240(8) 0.0280(9) 0.0273(9) 0.0019(7) -0.0014(7) -0.0051(7)
C2 0.0249(9) 0.0354(10) 0.0386(10) -0.0005(8) -0.0102(8) -0.0016(8)
C3 0.0279(9) 0.0371(10) 0.0325(10) -0.0009(8) -0.0098(8) -0.0059(8)
S10 0.0375(3) 0.0433(3) 0.0394(3) 0.0013(2) 0.0003(2) -0.0099(2)
O10 0.0431(8) 0.0618(10) 0.0410(8) 0.0035(7) 0.0096(6) -0.0032(7)
C11 0.0423(13) 0.081(2) 0.0531(15) -0.0136(14) -0.0046(11) -0.0195(13)
C12 0.0497(14) 0.080(2) 0.0407(13) -0.0033(13) -0.0044(11) -0.0175(14)

_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 C1 1.487(2) . ?
N1 H1N 0.92(2) . ?
N1 H2N 0.92(2) . ?
N1 H3N 0.84(2) . ?
C1 C2 1.512(2) . ?
C1 C3 1.514(2) . ?
C1 H1 0.936(17) . ?
C2 C3 1.527(2) 2_765 ?
C2 H2A 0.956(18) . ?
C2 H2B 0.97(2) . ?
C3 C2 1.527(2) 2_765 ?
C3 H3A 0.969(15) . ?
C3 H3B 0.944(18) . ?
S10 O10 1.5088(14) . ?
S10 C11 1.769(2) . ?
S10 C12 1.781(2) . ?
C11 H11A 0.885(16) . ?
C11 H11B 0.94(2) . ?
C11 H11C 0.94(3) . ?
C12 H12A 0.93(2) . ?
C12 H12B 0.98(2) . ?
C12 H12C 0.86(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1N 113.8(12) . . ?
C1 N1 H2N 114.6(13) . . ?
H1N N1 H2N 104.9(17) . . ?
C1 N1 H3N 111.0(13) . . ?
H1N N1 H3N 106.0(19) . . ?
H2N N1 H3N 105.7(18) . . ?
N1 C1 C2 110.38(13) . . ?
N1 C1 C3 110.01(14) . . ?
C2 C1 C3 112.04(15) . . ?
N1 C1 H1 105.4(10) . . ?
C2 C1 H1 109.4(9) . . ?
C3 C1 H1 109.4(10) . . ?
C1 C2 C3 110.05(14) . 2_765 ?
C1 C2 H2A 108.1(10) . . ?
C3 C2 H2A 109.1(10) 2_765 . ?
C1 C2 H2B 110.8(10) . . ?
C3 C2 H2B 112.5(11) 2_765 . ?
H2A C2 H2B 106.1(14) . . ?
C1 C3 C2 109.92(14) . 2_765 ?
C1 C3 H3A 108.8(10) . . ?
C2 C3 H3A 112.8(9) 2_765 . ?
C1 C3 H3B 106.0(11) . . ?
C2 C3 H3B 111.5(11) 2_765 . ?
H3A C3 H3B 107.5(14) . . ?
O10 S10 C11 106.44(11) . . ?
O10 S10 C12 105.37(11) . . ?
C11 S10 C12 97.56(14) . . ?
S10 C11 H11A 107.7(14) . . ?
S10 C11 H11B 108.2(14) . . ?
H11A C11 H11B 108(2) . . ?
S10 C11 H11C 105.6(17) . . ?
H11A C11 H11C 115(2) . . ?
H11B C11 H11C 111(2) . . ?
S10 C12 H12A 108.5(16) . . ?
S10 C12 H12B 106.7(14) . . ?
H12A C12 H12B 116(2) . . ?
S10 C12 H12C 110.4(16) . . ?
H12A C12 H12C 103(2) . . ?
H12B C12 H12C 112(2) . . ?

_diffrn_measured_fraction_theta_max 0.865
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.044

# Attachment 'dace_monochloride.cif'

data_exp_85_abs
_database_code_depnum_ccdc_archive 'CCDC 696304'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'1-ammonio-2-amine-cyclohexane chloride'
;
_chemical_name_common            
;
'1-ammonio-2-amine-cyclohexane chloride'
;
_chemical_formula_moiety         'C6 H15 N2, Cl'
_chemical_formula_sum            'C6 H15 Cl N2'
_chemical_formula_weight         150.65

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   7.4694(2)
_cell_length_b                   15.3118(3)
_cell_length_c                   8.0970(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.144(3)
_cell_angle_gamma                90.00
_cell_volume                     869.41(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8550
_cell_measurement_theta_min      2.6526
_cell_measurement_theta_max      29.2870

_diffrn_measurement_method       'omega scan'
_diffrn_measurement_device_type  xcalibur
_diffrn_measurement_device       '95mm CCD camera (sapphire) on κ-goniostat'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            18139
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         29.38
_reflns_number_total             2180
_reflns_number_gt                1660
_reflns_threshold_expression     >2sigma(I)
_diffrn_orient_matrix_UB_11      0.0231436808
_diffrn_orient_matrix_UB_12      0.0333565008
_diffrn_orient_matrix_UB_13      -0.0500481577
_diffrn_orient_matrix_UB_21      -0.0287648353
_diffrn_orient_matrix_UB_22      -0.0275590081
_diffrn_orient_matrix_UB_23      -0.0750589341
_diffrn_orient_matrix_UB_31      -0.0942959358
_diffrn_orient_matrix_UB_32      0.0167074620
_diffrn_orient_matrix_UB_33      -0.0239174155
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega 6.00 56.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.2830 0.0000 30.0000 0.0000 0.0000 50

#__ type_ start__ end____ width___ exp.time_
2 omega -39.00 13.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.2830 -77.0000 60.0000 0.0000 0.0000 52

#__ type_ start__ end____ width___ exp.time_
3 omega -9.00 56.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.2830 0.0000 90.0000 0.0000 0.0000 65

#__ type_ start__ end____ width___ exp.time_
4 omega -88.00 6.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.2830 -45.0000 270.0000 0.0000 0.0000 94

#__ type_ start__ end____ width___ exp.time_
5 omega -87.00 -35.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.2830 -77.0000 90.0000 0.0000 0.0000 52

#__ type_ start__ end____ width___ exp.time_
6 omega -87.00 -9.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.2830 144.0000 -5.0000 0.0000 0.0000 78

#__ type_ start__ end____ width___ exp.time_
7 omega -41.00 9.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.2830 45.0000 0.0000 0.0000 0.0000 50

#__ type_ start__ end____ width___ exp.time_
8 omega 5.00 54.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.2830 45.0000 120.0000 0.0000 0.0000 49

#__ type_ start__ end____ width___ exp.time_
9 omega -42.00 6.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.2830 -45.0000 90.0000 0.0000 0.0000 48

#__ type_ start__ end____ width___ exp.time_
10 omega -47.00 -3.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.2830 77.0000 300.0000 0.0000 0.0000 44

#__ type_ start__ end____ width___ exp.time_
11 omega -41.00 9.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.2830 45.0000 240.0000 0.0000 0.0000 50

#__ type_ start__ end____ width___ exp.time_
12 omega -38.00 13.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -17.2830 -77.0000 180.0000 0.0000 0.0000 51

#__ type_ start__ end____ width___ exp.time_
13 omega 29.00 71.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 -116.0000 11.0000 0.0000 0.0000 42

#__ type_ start__ end____ width___ exp.time_
14 omega 41.00 90.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 45.0000 90.0000 0.0000 0.0000 49

#__ type_ start__ end____ width___ exp.time_
15 omega 5.00 54.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 -86.0000 309.0000 0.0000 0.0000 49

#__ type_ start__ end____ width___ exp.time_
16 omega 46.00 90.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 45.0000 0.0000 0.0000 0.0000 44

#__ type_ start__ end____ width___ exp.time_
17 omega 36.00 78.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 -127.0000 162.0000 0.0000 0.0000 42

#__ type_ start__ end____ width___ exp.time_
18 omega 47.00 77.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 0.0000 150.0000 0.0000 0.0000 30

#__ type_ start__ end____ width___ exp.time_
19 omega -4.00 21.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 45.0000 210.0000 0.0000 0.0000 25

#__ type_ start__ end____ width___ exp.time_
20 omega -4.00 34.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 45.0000 330.0000 0.0000 0.0000 38

#__ type_ start__ end____ width___ exp.time_
21 omega -51.00 -26.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 19.1580 -77.0000 210.0000 0.0000 0.0000 25

;

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4252
_exptl_crystal_size_mid          0.3344
_exptl_crystal_size_min          0.1268
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0548P)²+0.0000P] 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_number_reflns         2180
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
Cl1 Cl 0.51020(5) 0.36348(2) 0.73284(4) 0.05187(15) Uani 1 1 d . . .
N1 N 0.37155(14) 0.07535(8) 0.79900(16) 0.0408(3) Uani 1 1 d . . .
H1N H 0.4083(19) 0.0857(9) 0.913(2) 0.048(4) Uiso 1 1 d . . .
H2N H 0.3931(19) 0.0245(11) 0.7905(17) 0.047(4) Uiso 1 1 d . . .
N2 N -0.41206(15) 0.16815(8) 0.64285(17) 0.0389(3) Uani 1 1 d . . .
H4N H -0.4411(18) 0.1588(9) 0.530(2) 0.041(4) Uiso 1 1 d . . .
H5N H -0.483(2) 0.1344(11) 0.692(2) 0.069(5) Uiso 1 1 d . . .
H6N H -0.4360(18) 0.2217(11) 0.6568(17) 0.045(4) Uiso 1 1 d . . .
C1 C 0.16641(16) 0.09378(8) 0.72024(16) 0.0339(3) Uani 1 1 d . . .
H1 H 0.1360(16) 0.0863(8) 0.6010(16) 0.035(3) Uiso 1 1 d . . .
C2 C 0.12721(18) 0.18740(8) 0.7587(2) 0.0416(3) Uani 1 1 d . . .
H2A H 0.1649(17) 0.1922(9) 0.8843(18) 0.043(4) Uiso 1 1 d . . .
H2B H 0.200(2) 0.2236(10) 0.7200(18) 0.050(4) Uiso 1 1 d . . .
C3 C -0.08360(18) 0.20992(8) 0.6744(2) 0.0410(3) Uani 1 1 d . . .
H3A H -0.1196(18) 0.2041(9) 0.5515(18) 0.042(4) Uiso 1 1 d . . .
H3B H -0.1075(19) 0.2672(9) 0.6984(18) 0.047(4) Uiso 1 1 d . . .
C4 C -0.20680(16) 0.14722(8) 0.73252(16) 0.0347(3) Uani 1 1 d . . .
H4 H -0.1833(16) 0.1545(7) 0.8554(17) 0.032(3) Uiso 1 1 d . . .
C5 C -0.16815(17) 0.05289(8) 0.6960(2) 0.0406(3) Uani 1 1 d . . .
H5A H -0.2053(18) 0.0462(9) 0.5700(19) 0.047(4) Uiso 1 1 d . . .
H5B H -0.242(2) 0.0165(10) 0.7353(18) 0.056(4) Uiso 1 1 d . . .
C6 C 0.04283(18) 0.03127(9) 0.7802(2) 0.0415(3) Uani 1 1 d . . .
H6A H 0.0808(19) 0.0367(9) 0.9060(18) 0.047(4) Uiso 1 1 d . . .
H6B H 0.0695(18) -0.0281(11) 0.7568(17) 0.050(4) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0694(3) 0.0374(2) 0.0450(2) 0.00059(13) 0.01490(16) 0.00045(14)
N1 0.0379(6) 0.0400(7) 0.0466(7) 0.0013(5) 0.0174(5) 0.0049(5)
N2 0.0362(6) 0.0380(6) 0.0460(7) -0.0017(5) 0.0186(5) 0.0024(4)
C1 0.0340(6) 0.0375(7) 0.0323(6) 0.0004(5) 0.0141(5) 0.0014(5)
C2 0.0370(7) 0.0342(7) 0.0567(9) 0.0017(6) 0.0203(6) -0.0040(5)
C3 0.0393(7) 0.0307(7) 0.0549(9) 0.0039(6) 0.0187(6) 0.0016(5)
C4 0.0341(6) 0.0360(7) 0.0362(6) -0.0019(5) 0.0149(5) -0.0004(5)
C5 0.0380(7) 0.0311(6) 0.0544(8) 0.0010(5) 0.0180(6) -0.0035(5)
C6 0.0415(7) 0.0314(7) 0.0539(8) 0.0059(6) 0.0192(6) 0.0010(5)

_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 C1 1.4701(16) . ?
N1 H1N 0.884(15) . ?
N1 H2N 0.803(16) . ?
N2 C4 1.4879(15) . ?
N2 H4N 0.874(15) . ?
N2 H5N 0.93(2) . ?
N2 H6N 0.855(16) . ?
C1 C2 1.5169(18) . ?
C1 C6 1.5207(17) . ?
C1 H1 0.920(12) . ?
C2 C3 1.5245(18) . ?
C2 H2A 0.960(13) . ?
C2 H2B 0.903(15) . ?
C3 C4 1.5127(17) . ?
C3 H3A 0.942(14) . ?
C3 H3B 0.929(14) . ?
C4 C5 1.5218(17) . ?
C4 H4 0.955(12) . ?
C5 C6 1.5225(18) . ?
C5 H5A 0.966(14) . ?
C5 H5B 0.916(15) . ?
C6 H6A 0.962(13) . ?
C6 H6B 0.963(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1N 108.7(9) . . ?
C1 N1 H2N 111.0(10) . . ?
H1N N1 H2N 105.4(13) . . ?
C4 N2 H4N 108.5(9) . . ?
C4 N2 H5N 108.5(10) . . ?
H4N N2 H5N 112.8(13) . . ?
C4 N2 H6N 111.7(9) . . ?
H4N N2 H6N 107.9(12) . . ?
H5N N2 H6N 107.5(13) . . ?
N1 C1 C2 109.78(10) . . ?
N1 C1 C6 113.41(10) . . ?
C2 C1 C6 110.35(10) . . ?
N1 C1 H1 106.0(7) . . ?
C2 C1 H1 109.8(8) . . ?
C6 C1 H1 107.4(8) . . ?
C1 C2 C3 111.37(10) . . ?
C1 C2 H2A 106.4(8) . . ?
C3 C2 H2A 109.8(8) . . ?
C1 C2 H2B 109.1(9) . . ?
C3 C2 H2B 110.9(9) . . ?
H2A C2 H2B 109.2(11) . . ?
C4 C3 C2 111.24(10) . . ?
C4 C3 H3A 106.6(8) . . ?
C2 C3 H3A 109.1(8) . . ?
C4 C3 H3B 110.7(8) . . ?
C2 C3 H3B 111.3(9) . . ?
H3A C3 H3B 107.8(11) . . ?
N2 C4 C3 110.28(10) . . ?
N2 C4 C5 110.01(10) . . ?
C3 C4 C5 111.44(10) . . ?
N2 C4 H4 105.8(7) . . ?
C3 C4 H4 109.6(7) . . ?
C5 C4 H4 109.5(7) . . ?
C4 C5 C6 110.83(10) . . ?
C4 C5 H5A 107.5(8) . . ?
C6 C5 H5A 109.1(8) . . ?
C4 C5 H5B 109.3(9) . . ?
C6 C5 H5B 111.6(9) . . ?
H5A C5 H5B 108.3(11) . . ?
C1 C6 C5 111.63(10) . . ?
C1 C6 H6A 107.1(8) . . ?
C5 C6 H6A 109.7(8) . . ?
C1 C6 H6B 110.0(8) . . ?
C5 C6 H6B 111.7(8) . . ?
H6A C6 H6B 106.6(11) . . ?

_diffrn_measured_fraction_theta_max 0.909
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.045


