# Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Dimitrii S Yufit'
_publ_contact_author_email       D.S.YUFIT@DURHAM.AC.UK

_publ_section_title              
;
Low-melting molecular complexes of chloroform.
;
loop_
_publ_author_name
'Dimitrii S Yufit'
'J. A. K. Howard'

# Attachment 'chloroform_solvates_rev.cif'

data_1_mc
_database_code_depnum_ccdc_archive 'CCDC 741273'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Methanol chloroform clathrate (1:1)
;
_chemical_name_common            'Methanol chloroform clathrate (1:1)'
_chemical_melting_point          -85
_chemical_formula_moiety         'C H Cl3, C H4 O'
_chemical_formula_sum            'C2 H5 Cl3 O'
_chemical_formula_weight         151.41

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P c a 21 '
_symmetry_space_group_name_Hall  'P 2c -2ac '
_symmetry_int_tables_number      29

_chemical_absolute_configuration ad

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

_cell_length_a                   18.210(4)
_cell_length_b                   7.692(2)
_cell_length_c                   4.6608(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     652.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    185(2)
_cell_measurement_reflns_used    515
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      21.58

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    1.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (Bruker-AXS, 2003)
;
_exptl_absorpt_correction_T_min  0.5665
_exptl_absorpt_correction_T_max  0.6997

_exptl_special_details           
;
Crystal was grown in situ on the diffractometer by slow
cooling of the mixture of two components sealed in borosilicate
capillary 0.3 mm in diameter
;

_diffrn_ambient_temperature      185(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '0.30° ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4194
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         27.00
_reflns_number_total             1178
_reflns_number_gt                905
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART Ver. 5.630 (Bruker-AXS, 2003)'
_computing_cell_refinement       'SAINT Ver. 6.45 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.45'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'

_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)+(0.0750P)²+0.0700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_number_reflns         1178
_refine_ls_number_parameters     63
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.43442(8) 0.07249(18) 0.3231(5) 0.0709(4) Uani 1 1 d . . .
Cl2 Cl 0.32118(6) 0.33263(17) 0.3228(5) 0.0698(4) Uani 1 1 d . . .
Cl3 Cl 0.45110(8) 0.37637(19) 0.6777(5) 0.0734(5) Uani 1 1 d . . .
O1 O 0.2103(2) 0.9197(4) 0.3010(11) 0.0507(10) Uani 1 1 d . . .
C1 C 0.3886(3) 0.2277(6) 0.5324(14) 0.0493(11) Uani 1 1 d . . .
C2 C 0.1669(3) 0.7667(6) 0.3193(17) 0.0645(13) Uani 1 1 d . . .
H2A H 0.1979 0.6647 0.2848 0.097 Uiso 1 1 calc R . .
H2B H 0.1278 0.7712 0.1749 0.097 Uiso 1 1 calc R . .
H2C H 0.1450 0.7587 0.5110 0.097 Uiso 1 1 calc R . .
H1O H 0.225(3) 0.935(5) 0.448(14) 0.032(14) Uiso 1 1 d . . .
H1 H 0.366(2) 0.168(5) 0.665(13) 0.040(12) 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 0.0806(8) 0.0693(7) 0.0629(11) -0.0084(8) -0.0025(8) 0.0271(6)
Cl2 0.0576(6) 0.0799(8) 0.0718(11) 0.0104(8) 0.0049(8) 0.0199(5)
Cl3 0.0770(8) 0.0717(8) 0.0715(12) -0.0046(8) 0.0015(8) -0.0275(6)
O1 0.066(2) 0.0458(15) 0.040(3) 0.0024(16) -0.005(2) -0.0049(13)
C1 0.053(2) 0.051(3) 0.044(4) 0.001(2) 0.008(2) -0.0035(19)
C2 0.079(3) 0.048(2) 0.066(4) 0.005(3) 0.000(3) -0.012(2)

_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 1.753(6) . yes
Cl2 C1 1.764(6) . yes
Cl3 C1 1.750(5) . yes
O1 C2 1.420(5) . yes
O1 H1O 0.75(6) . ?
C1 H1 0.87(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 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
C2 O1 H1O 106(4) . . ?
Cl3 C1 Cl1 110.5(3) . . yes
Cl3 C1 Cl2 111.6(3) . . yes
Cl1 C1 Cl2 109.6(4) . . yes
Cl3 C1 H1 112(3) . . ?
Cl1 C1 H1 105(3) . . ?
Cl2 C1 H1 108(3) . . ?
O1 C2 H2A 109.5 . . ?
O1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O1 0.75(6) 2.02(5) 2.743(4) 162(5) 4

_diffrn_measured_fraction_theta_max 0.884
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.884
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.068

# File processed with modiCIFer Dec. 16,2005. I.A.Guzei, UW-Madison.
#==END

data_II_CCP
_database_code_depnum_ccdc_archive 'CCDC 741274'

_audit_creation_method           SHELXL-97
_chemical_formula_moiety         'C H Cl3, C5 H8 O'
_chemical_formula_sum            'C6 H9 Cl3 O'
_chemical_formula_weight         203.48
_chemical_melting_point          '-93 -95C'
_chemical_name_common            'cyclopentanone chloroform clathrate (1:1)'
_chemical_name_systematic        'cyclopentanone chloroform clathrate (1:1)'
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'
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 1 21/n 1'
_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_angle_alpha                90.00
_cell_angle_beta                 106.05(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9104(13)
_cell_length_b                   9.6599(14)
_cell_length_c                   10.1505(15)
_cell_measurement_reflns_used    2893
_cell_measurement_temperature    178(1)
_cell_measurement_theta_max      2.54
_cell_measurement_theta_min      29.78
_cell_volume                     933.9(2)
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_F_000             416
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
Crystal was grown in situ on the diffractometer by slow
cooling of the mixture of two components sealed in borosilicate
capillary 0.3 mm in diameter
;
_diffrn_ambient_temperature      178(1)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.807
_diffrn_measured_fraction_theta_max 0.807
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7481
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.54
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           25.0
_diffrn_source_power             1.25
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1598
_reflns_number_total             1999
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    
;
Olex2, Durham University (compiled Apr 2 2009 15:09:25)
;
_computing_publication_material  
;
Olex2, Durham University (compiled Apr 2 2009 15:09:25)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.048
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0352
_refine_ls_extinction_coef       0.039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0994
_refine_ls_weighting_details     
;
calc w=1/[σ²(Fo²)+(0.0500P)²+0.3000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_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.
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.67538(7) 0.29322(5) 0.42381(5) 0.0527(2) Uani 1 1 d . . .
Cl2 Cl 0.76874(8) 0.44151(7) 0.67732(7) 0.0748(3) Uani 1 1 d . . .
Cl3 Cl 0.88174(8) 0.17067(7) 0.64793(8) 0.0779(3) Uani 1 1 d . . .
C1S C 0.8182(2) 0.32712(19) 0.56502(19) 0.0384(5) Uani 1 1 d . . .
O1 O 0.86118(16) 0.60257(15) 0.40412(18) 0.0558(4) Uani 1 1 d . . .
C1 C 0.7649(2) 0.68384(19) 0.3903(2) 0.0413(5) Uani 1 1 d . . .
C2 C 0.7759(3) 0.8274(3) 0.4505(3) 0.0560(6) Uani 1 1 d . . .
C3 C 0.6252(3) 0.8746(3) 0.4285(3) 0.0619(7) Uani 1 1 d . . .
C4 C 0.5443(3) 0.7999(2) 0.2993(3) 0.0522(6) Uani 1 1 d . . .
C5 C 0.6159(3) 0.6596(2) 0.3101(3) 0.0550(6) Uani 1 1 d . . .
H1 H 0.889(2) 0.368(2) 0.539(2) 0.047(6) Uiso 1 1 d . . .
H21 H 0.824(4) 0.826(3) 0.543(4) 0.093(11) Uiso 1 1 d . . .
H22 H 0.824(3) 0.882(3) 0.398(3) 0.086(9) Uiso 1 1 d . . .
H31 H 0.596(4) 0.835(4) 0.517(4) 0.103(11) Uiso 1 1 d . . .
H32 H 0.616(3) 0.973(4) 0.426(3) 0.089(10) Uiso 1 1 d . . .
H41 H 0.436(4) 0.798(3) 0.293(3) 0.076(9) Uiso 1 1 d . . .
H42 H 0.556(3) 0.851(3) 0.222(3) 0.073(8) Uiso 1 1 d . . .
H51 H 0.573(3) 0.593(3) 0.365(3) 0.089(10) Uiso 1 1 d . . .
H52 H 0.612(3) 0.623(4) 0.225(3) 0.091(10) 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 0.0568(5) 0.0501(3) 0.0431(3) 0.00121(19) 0.0004(3) -0.0120(2)
Cl2 0.0966(6) 0.0746(4) 0.0677(4) -0.0328(3) 0.0468(4) -0.0378(4)
Cl3 0.0552(5) 0.0660(4) 0.0985(5) 0.0422(4) -0.0020(4) -0.0049(3)
C1S 0.0340(14) 0.0416(9) 0.0390(9) 0.0034(7) 0.0089(9) -0.0076(8)
O1 0.0382(11) 0.0454(8) 0.0849(11) 0.0195(7) 0.0187(8) 0.0067(6)
C1 0.0377(15) 0.0380(9) 0.0489(11) 0.0121(8) 0.0131(10) -0.0008(8)
C2 0.0518(18) 0.0535(13) 0.0603(15) -0.0116(10) 0.0114(13) -0.0044(10)
C3 0.0570(19) 0.0536(14) 0.0754(17) -0.0110(12) 0.0191(14) 0.0070(11)
C4 0.0459(18) 0.0421(11) 0.0658(14) 0.0077(9) 0.0109(12) 0.0078(9)
C5 0.0428(18) 0.0367(10) 0.0795(17) -0.0011(10) 0.0066(13) 0.0004(9)

_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 C1S 1.745(2) . ?
Cl2 C1S 1.752(2) . ?
Cl3 C1S 1.759(2) . ?
C1S H1 0.90(2) . ?
O1 C1 1.213(2) . ?
C1 C5 1.494(4) . ?
C1 C2 1.507(3) . ?
C2 C3 1.517(4) . ?
C2 H21 0.93(4) . ?
C2 H22 0.96(3) . ?
C3 C4 1.518(4) . ?
C3 H31 1.09(4) . ?
C3 H32 0.95(3) . ?
C4 C5 1.519(3) . ?
C4 H41 1.05(3) . ?
C4 H42 0.96(3) . ?
C5 H51 1.02(3) . ?
C5 H52 0.93(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
Cl1 C1S Cl2 110.09(12) . . ?
Cl1 C1S Cl3 109.48(10) . . ?
Cl2 C1S Cl3 110.98(11) . . ?
Cl1 C1S H1 111.0(15) . . ?
Cl2 C1S H1 107.0(14) . . ?
Cl3 C1S H1 108.3(15) . . ?
O1 C1 C5 126.1(2) . . ?
O1 C1 C2 125.6(2) . . ?
C5 C1 C2 108.34(19) . . ?
C1 C2 C3 105.0(2) . . ?
C1 C2 H21 111(2) . . ?
C3 C2 H21 111(2) . . ?
C1 C2 H22 105.9(18) . . ?
C3 C2 H22 111.7(19) . . ?
H21 C2 H22 112(3) . . ?
C2 C3 C4 104.3(2) . . ?
C2 C3 H31 104.5(19) . . ?
C4 C3 H31 110.6(19) . . ?
C2 C3 H32 113(2) . . ?
C4 C3 H32 115(2) . . ?
H31 C3 H32 109(3) . . ?
C3 C4 C5 103.7(2) . . ?
C3 C4 H41 110.3(15) . . ?
C5 C4 H41 115.9(15) . . ?
C3 C4 H42 107.8(18) . . ?
C5 C4 H42 110.8(17) . . ?
H41 C4 H42 108(2) . . ?
C1 C5 C4 105.75(19) . . ?
C1 C5 H51 107.4(18) . . ?
C4 C5 H51 110.1(18) . . ?
C1 C5 H52 110(2) . . ?
C4 C5 H52 112(2) . . ?
H51 C5 H52 111(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1S H1 O1 0.90(2) 2.62(2) 3.211(2) 123.8(18) .
C1S H1 O1 0.90(2) 2.40(2) 3.179(3) 144.1(19) 3_766
#==END

#3. data
data_III_cchon
_database_code_depnum_ccdc_archive 'CCDC 741275'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
cyclohexanone chloroform clathrate (1:1)
;
_chemical_name_common            'cyclohexanone chloroform clathrate (1:1)'
_chemical_melting_point          -65
_chemical_formula_moiety         'C6 H10 O, C H Cl3'
_chemical_formula_sum            'C7 H11 Cl3 O'
_chemical_formula_weight         217.51

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'
Cl Cl 0.1484 0.1585 '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 '
_symmetry_int_tables_number      2

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

_cell_length_a                   6.0440(12)
_cell_length_b                   9.0987(18)
_cell_length_c                   9.5963(19)
_cell_angle_alpha                98.82(3)
_cell_angle_beta                 100.43(3)
_cell_angle_gamma                97.22(3)
_cell_volume                     506.44(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      30.00

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
Crystal was grown in situ on the diffractometer by slow
cooling of the mixture of two components sealed in borosilicate
capillary 0.3 mm in diameter
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '0.30° ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4457
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         30.00
_reflns_number_total             2253
_reflns_number_gt                1955
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART Ver. 5.630 (Bruker-AXS, 2003)'
_computing_cell_refinement       'SAINT Ver. 6.45 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.45'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'

_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)+(0.0400P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2253
_refine_ls_number_parameters     144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.30269(7) 0.80497(5) 0.78546(4) 0.05150(14) Uani 1 1 d . . .
Cl2 Cl 0.62134(10) 0.64402(5) 0.66096(5) 0.06239(16) Uani 1 1 d . . .
Cl3 Cl 0.77774(7) 0.93482(5) 0.84440(4) 0.05634(15) Uani 1 1 d . . .
C1S C 0.5510(3) 0.82272(15) 0.71553(14) 0.0374(3) Uani 1 1 d . . .
O1 O 0.4077(3) 0.12943(16) 0.60199(13) 0.0614(4) Uani 1 1 d . . .
C1 C 0.2714(3) 0.18011(16) 0.66664(15) 0.0412(4) Uani 1 1 d . . .
C2 C 0.0385(3) 0.19789(17) 0.59204(16) 0.0446(4) Uani 1 1 d . . .
C3 C -0.0253(3) 0.3501(2) 0.64509(18) 0.0521(4) Uani 1 1 d . . .
C4 C 0.0079(4) 0.3810(2) 0.80885(19) 0.0546(4) Uani 1 1 d . . .
C5 C 0.2521(3) 0.37650(19) 0.87780(17) 0.0500(4) Uani 1 1 d . . .
C6 C 0.3229(3) 0.2259(2) 0.82809(15) 0.0474(4) Uani 1 1 d . . .
H1S H 0.528(3) 0.8689(18) 0.6385(18) 0.042(4) Uiso 1 1 d . . .
H21 H -0.064(3) 0.124(2) 0.6101(19) 0.048(5) Uiso 1 1 d . . .
H22 H 0.032(3) 0.180(2) 0.490(2) 0.058(5) Uiso 1 1 d . . .
H31 H 0.079(4) 0.429(2) 0.612(2) 0.061(5) Uiso 1 1 d . . .
H32 H -0.188(4) 0.352(2) 0.603(2) 0.065(6) Uiso 1 1 d . . .
H41 H -0.086(4) 0.306(2) 0.834(2) 0.057(5) Uiso 1 1 d . . .
H42 H -0.027(4) 0.477(3) 0.841(2) 0.074(6) Uiso 1 1 d . . .
H51 H 0.349(4) 0.462(2) 0.854(2) 0.064(6) Uiso 1 1 d . . .
H52 H 0.276(4) 0.394(2) 0.981(2) 0.067(6) Uiso 1 1 d . . .
H61 H 0.233(4) 0.148(2) 0.868(2) 0.058(5) Uiso 1 1 d . . .
H62 H 0.485(4) 0.225(2) 0.860(2) 0.072(6) 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 0.0400(3) 0.0607(2) 0.0574(2) 0.01322(18) 0.01571(19) 0.01042(18)
Cl2 0.0807(4) 0.0493(2) 0.0686(3) 0.01435(19) 0.0298(3) 0.0277(2)
Cl3 0.0467(3) 0.0688(3) 0.0477(2) 0.01435(18) 0.00120(18) -0.00505(19)
C1S 0.0403(8) 0.0424(6) 0.0323(6) 0.0111(5) 0.0074(6) 0.0112(6)
O1 0.0759(10) 0.0803(8) 0.0455(6) 0.0226(6) 0.0275(7) 0.0425(8)
C1 0.0513(10) 0.0443(7) 0.0348(6) 0.0134(5) 0.0149(7) 0.0172(7)
C2 0.0499(10) 0.0449(7) 0.0352(6) 0.0015(5) 0.0039(6) 0.0072(7)
C3 0.0526(11) 0.0529(8) 0.0484(8) 0.0060(7) -0.0008(8) 0.0200(8)
C4 0.0586(12) 0.0549(9) 0.0503(9) -0.0022(7) 0.0116(8) 0.0222(9)
C5 0.0556(11) 0.0527(8) 0.0354(7) 0.0003(6) 0.0041(7) 0.0018(7)
C6 0.0467(10) 0.0677(10) 0.0334(6) 0.0161(6) 0.0098(7) 0.0191(8)

_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 C1S 1.7508(17) . yes
Cl2 C1S 1.7585(16) . yes
Cl3 C1S 1.7595(16) . yes
C1S H1S 0.903(17) . ?
O1 C1 1.212(2) . yes
C1 C2 1.499(2) . yes
C1 C6 1.505(2) . yes
C2 C3 1.521(2) . yes
C2 H21 0.913(19) . ?
C2 H22 0.96(2) . ?
C3 C4 1.525(2) . yes
C3 H31 1.02(2) . ?
C3 H32 1.00(2) . ?
C4 C5 1.512(3) . yes
C4 H41 0.92(2) . ?
C4 H42 0.94(2) . ?
C5 C6 1.520(3) . yes
C5 H51 1.00(2) . ?
C5 H52 0.96(2) . ?
C6 H61 1.00(2) . ?
C6 H62 0.98(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
Cl1 C1S Cl2 110.23(8) . . yes
Cl1 C1S Cl3 110.45(8) . . yes
Cl2 C1S Cl3 110.29(9) . . yes
Cl1 C1S H1S 109.3(11) . . ?
Cl2 C1S H1S 108.9(10) . . ?
Cl3 C1S H1S 107.6(11) . . ?
O1 C1 C2 122.44(14) . . yes
O1 C1 C6 122.06(15) . . yes
C2 C1 C6 115.48(16) . . yes
C1 C2 C3 112.54(13) . . yes
C1 C2 H21 108.0(12) . . ?
C3 C2 H21 108.3(12) . . ?
C1 C2 H22 108.3(13) . . ?
C3 C2 H22 112.5(12) . . ?
H21 C2 H22 106.9(16) . . ?
C2 C3 C4 110.87(14) . . yes
C2 C3 H31 107.0(12) . . ?
C4 C3 H31 110.1(11) . . ?
C2 C3 H32 110.0(12) . . ?
C4 C3 H32 108.5(12) . . ?
H31 C3 H32 110.4(17) . . ?
C5 C4 C3 110.59(17) . . yes
C5 C4 H41 109.0(13) . . ?
C3 C4 H41 107.2(13) . . ?
C5 C4 H42 108.3(15) . . ?
C3 C4 H42 110.3(13) . . ?
H41 C4 H42 111(2) . . ?
C4 C5 C6 111.47(14) . . yes
C4 C5 H51 107.5(12) . . ?
C6 C5 H51 112.1(13) . . ?
C4 C5 H52 111.9(14) . . ?
C6 C5 H52 108.1(13) . . ?
H51 C5 H52 105.7(17) . . ?
C1 C6 C5 112.70(13) . . yes
C1 C6 H61 107.7(11) . . ?
C5 C6 H61 107.4(12) . . ?
C1 C6 H62 106.4(13) . . ?
C5 C6 H62 113.2(13) . . ?
H61 C6 H62 109.3(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1S H1S O1 0.903(17) 2.620(17) 3.305(2) 133.3(13) 1_565
C1S H1S O1 0.903(17) 2.411(17) 3.1924(19) 144.9(14) 2_666

_diffrn_measured_fraction_theta_max 0.762
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.762
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.043

# File processed with modiCIFer Dec. 16,2005. I.A.Guzei, UW-Madison.
#==END

#3. data
data_V_cdmf
_database_code_depnum_ccdc_archive 'CCDC 741276'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
dimethylformamide chloroform clathrate (1:1)
;
_chemical_name_common            'dimethylformamide chloroform clathrate (1:1)'
_chemical_melting_point          -83
_chemical_formula_moiety         'C3 H7 N O, C H Cl3'
_chemical_formula_sum            'C4 H8 Cl3 N O'
_chemical_formula_weight         192.46

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           Monoclinic
_symmetry_space_group_name_H-M   'C 1 c 1 '
_symmetry_space_group_name_Hall  'C -2yc '
_symmetry_int_tables_number      9

_chemical_absolute_configuration ad
# Options are 'rm', 'ad', 'rmad', 'syn', 'unk' or '.'
#
# rm : absolute configuration established by the structure determination
# of a compound containing a chiral reference molecule of known
# absolute configuration.
# ad : absolute configuration established by anomalous dispersion effects
# in diffraction measurements on the crystal.
# rmad : absolute configuration established by the structure determination
# of a compound containing a chiral reference molecule of known
# absolute configuration and confirmed by anomalous dispersion
# effects in diffraction measurements on the crystal.
# syn : absolute configuration has not been established by anomalous
# dispersion effects in diffraction measurements on the crystal.
# The enantiomer has been assigned by reference to an unchanging
# chiral centre in the synthetic procedure.
# unk : absolute configuration is unknown, there being no firm chemical
# evidence for its assignment to hand and it having not been
# established by anomalous dispersion effects in diffraction
# measurements on the crystal. An arbitrary choice of enantiomer
# has been made.
# . : inapplicable.
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'

_cell_length_a                   8.2840(7)
_cell_length_b                   8.6700(9)
_cell_length_c                   12.8290(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.10(3)
_cell_angle_gamma                90.00
_cell_volume                     880.68(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    185(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      27.98

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.971
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_special_details           
;
Crystal was grown in situ on the diffractometer by slow
cooling of the mixture of two components sealed in borosilicate
capillary 0.3 mm in diameter
;
_diffrn_ambient_temperature      185(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '0.30° ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6408
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         27.98
_reflns_number_total             1815
_reflns_number_gt                1666
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART Ver. 5.630 (Bruker-AXS, 2003)'
_computing_cell_refinement       'SAINT Ver. 6.45 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.45'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'

_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.28(14)
_refine_ls_number_reflns         1815
_refine_ls_number_parameters     115
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1326
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.85095(15) 0.06032(12) 0.26507(10) 0.0579(3) Uani 1 1 d . . .
Cl2 Cl 0.53646(14) 0.13761(13) 0.30628(9) 0.0554(3) Uani 1 1 d . . .
Cl3 Cl 0.76104(14) -0.08497(12) 0.44345(8) 0.0580(3) Uani 1 1 d . . .
N1 N 0.7151(4) 0.5559(3) 0.0623(3) 0.0403(7) Uani 1 1 d . . .
O1 O 0.5883(4) 0.7163(3) 0.1546(3) 0.0529(7) Uani 1 1 d . . .
C1 C 0.6846(5) -0.0112(4) 0.3108(3) 0.0419(7) Uani 1 1 d . . .
C2 C 0.6711(5) 0.6933(4) 0.0916(3) 0.0431(8) Uani 1 1 d . . .
C3 C 0.8136(8) 0.5395(6) -0.0129(5) 0.0618(12) Uani 1 1 d . . .
C4 C 0.6685(8) 0.4170(5) 0.1086(5) 0.0606(12) Uani 1 1 d . . .
H1 H 0.654(8) -0.102(7) 0.267(5) 0.055(14) Uiso 1 1 d . . .
H2 H 0.712(6) 0.780(6) 0.048(4) 0.043(12) Uiso 1 1 d . . .
H31 H 0.914(9) 0.462(8) 0.020(6) 0.066(17) Uiso 1 1 d . . .
H32 H 0.842(10) 0.655(8) -0.038(6) 0.071(18) Uiso 1 1 d . . .
H33 H 0.760(8) 0.476(8) -0.077(6) 0.066(16) Uiso 1 1 d . . .
H41 H 0.751(8) 0.361(6) 0.137(4) 0.041(12) Uiso 1 1 d . . .
H42 H 0.593(10) 0.350(10) 0.051(7) 0.09(2) Uiso 1 1 d . . .
H43 H 0.646(12) 0.438(8) 0.179(7) 0.08(2) 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 0.0621(8) 0.0546(5) 0.0678(6) 0.0099(4) 0.0358(5) 0.0049(4)
Cl2 0.0518(6) 0.0629(6) 0.0503(5) 0.0082(4) 0.0130(4) 0.0181(4)
Cl3 0.0694(8) 0.0520(4) 0.0533(5) 0.0205(4) 0.0192(4) 0.0119(4)
N1 0.045(2) 0.0347(13) 0.0441(14) -0.0017(11) 0.0178(13) 0.0025(10)
O1 0.062(2) 0.0417(12) 0.0600(15) -0.0163(11) 0.0257(14) -0.0026(11)
C1 0.049(2) 0.0366(14) 0.0410(15) -0.0023(12) 0.0154(14) -0.0006(13)
C2 0.046(2) 0.0331(13) 0.0491(18) -0.0006(13) 0.0126(15) 0.0004(12)
C3 0.069(4) 0.063(2) 0.066(3) 0.002(2) 0.041(2) 0.011(2)
C4 0.081(4) 0.0322(17) 0.078(3) 0.0025(18) 0.039(3) 0.0039(18)

_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 1.762(4) . yes
Cl2 C1 1.770(4) . yes
Cl3 C1 1.753(4) . yes
N1 C2 1.332(4) . yes
N1 C3 1.443(6) . yes
N1 C4 1.444(5) . yes
O1 C2 1.220(5) . yes
C1 H1 0.96(6) . ?
C2 H2 1.05(5) . ?
C3 H31 1.06(7) . ?
C3 H32 1.10(7) . ?
C3 H33 0.98(7) . ?
C4 H41 0.83(6) . ?
C4 H42 1.00(9) . ?
C4 H43 0.99(9) . ?

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
C2 N1 C3 122.2(3) . . yes
C2 N1 C4 120.1(3) . . yes
C3 N1 C4 117.7(3) . . yes
Cl3 C1 Cl1 110.9(2) . . yes
Cl3 C1 Cl2 110.3(2) . . yes
Cl1 C1 Cl2 109.59(19) . . yes
Cl3 C1 H1 103(4) . . ?
Cl1 C1 H1 101(4) . . ?
Cl2 C1 H1 121(4) . . ?
O1 C2 N1 125.9(3) . . yes
O1 C2 H2 125(3) . . ?
N1 C2 H2 109(3) . . ?
N1 C3 H31 109(4) . . ?
N1 C3 H32 109(4) . . ?
H31 C3 H32 119(5) . . ?
N1 C3 H33 114(4) . . ?
H31 C3 H33 95(5) . . ?
H32 C3 H33 110(5) . . ?
N1 C4 H41 113(4) . . ?
N1 C4 H42 111(5) . . ?
H41 C4 H42 104(6) . . ?
N1 C4 H43 111(4) . . ?
H41 C4 H43 93(6) . . ?
H42 C4 H43 123(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O1 0.96(6) 2.10(6) 3.049(4) 173(5) 1_545

_diffrn_measured_fraction_theta_max 0.867
_diffrn_reflns_theta_full        27.98
_diffrn_measured_fraction_theta_full 0.867
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.082

# File processed with modiCIFer Dec. 16,2005. I.A.Guzei, UW-Madison.

#==END
data_IV_CDEAS
_database_code_depnum_ccdc_archive 'CCDC 741277'

_audit_creation_method           SHELXL-97
_chemical_formula_moiety         'C H Cl3, C4 H11 N'
_chemical_formula_sum            'C5 H12 Cl3 N'
_chemical_formula_weight         192.51
_chemical_melting_point          -99
_chemical_name_common            'diethylamine chloroform clathrate (1:1)'
_chemical_name_systematic        
;
diethylamine chloroform clathrate (1:1)
;
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_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1434(9)
_cell_length_b                   10.4147(15)
_cell_length_c                   13.2477(18)
_cell_measurement_reflns_used    3347
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.56
_cell_measurement_theta_min      2.49
_cell_volume                     985.6(2)
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.3036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.0226 before and 0.0137 after correction.
The Ratio of minimum to maximum transmission is 0.407079646018.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_F_000             400
_exptl_crystal_colour            'dull colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
Crystal was grown in situ on the diffractometer by slow
cooling of the mixture of two components sealed in borosilicate
capillary 0.3 mm in diameter
;
_diffrn_ambient_temperature      153(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.828
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7967
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.49
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1947
_reflns_number_total             2164
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    
;
Olex2, Durham University (compiled Mar 6 2009 16:11:20)
;
_computing_publication_material  
;
Olex2, Durham University (compiled Mar 6 2009 16:11:20)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.045
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0365
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0991
_refine_ls_weighting_details     
;
calc w=1/[σ²(Fo²)+(0.0500P)²+0.4000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_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.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.50098(16) 0.34170(7) 0.45940(5) 0.0708(3) Uani 1 1 d . . .
Cl2 Cl 0.53171(13) 0.24727(7) 0.66210(5) 0.0603(2) Uani 1 1 d . . .
Cl3 Cl 0.47735(15) 0.51850(7) 0.62741(8) 0.0802(3) Uani 1 1 d . . .
N1 N 0.9787(3) 0.50326(16) 0.60076(13) 0.0367(4) Uani 1 1 d . . .
C1 C 0.9795(5) 0.6243(2) 0.54486(17) 0.0457(6) Uani 1 1 d . . .
C2 C 0.9733(7) 0.6001(3) 0.4319(2) 0.0618(9) Uani 1 1 d . . .
C3 C 0.9973(5) 0.5225(2) 0.71013(16) 0.0416(6) Uani 1 1 d . . .
C4 C 1.0170(5) 0.3947(2) 0.76402(18) 0.0508(7) Uani 1 1 d . . .
C5 C 0.5818(4) 0.3775(2) 0.58109(18) 0.0408(6) Uani 1 1 d . . .
H1N H 1.069(5) 0.461(3) 0.584(2) 0.043(8) Uiso 1 1 d . . .
H11 H 0.867(5) 0.676(3) 0.560(3) 0.059(10) Uiso 1 1 d . . .
H12 H 1.107(5) 0.671(3) 0.565(2) 0.049(8) Uiso 1 1 d . . .
H21 H 1.077(6) 0.559(4) 0.408(3) 0.072(13) Uiso 1 1 d . . .
H22 H 0.874(6) 0.540(4) 0.419(3) 0.072(11) Uiso 1 1 d . . .
H23 H 0.983(5) 0.679(3) 0.394(2) 0.061(9) Uiso 1 1 d . . .
H31 H 0.880(5) 0.571(3) 0.735(3) 0.054(9) Uiso 1 1 d . . .
H32 H 1.109(5) 0.581(3) 0.718(2) 0.047(8) Uiso 1 1 d . . .
H41 H 1.133(6) 0.343(4) 0.737(3) 0.069(11) Uiso 1 1 d . . .
H42 H 0.900(5) 0.336(3) 0.748(2) 0.054(9) Uiso 1 1 d . . .
H43 H 1.031(5) 0.407(3) 0.832(3) 0.061(9) Uiso 1 1 d . . .
H5 H 0.710(5) 0.393(3) 0.577(2) 0.040(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 0.0961(8) 0.0697(4) 0.0466(3) 0.0051(3) -0.0217(4) -0.0247(5)
Cl2 0.0654(6) 0.0645(4) 0.0508(3) 0.0106(3) 0.0038(3) -0.0084(4)
Cl3 0.0519(6) 0.0529(4) 0.1359(8) -0.0342(4) 0.0048(5) 0.0046(4)
N1 0.0396(14) 0.0315(8) 0.0391(8) -0.0031(6) 0.0020(9) -0.0014(9)
C1 0.056(2) 0.0348(10) 0.0464(11) 0.0005(8) 0.0025(13) -0.0023(12)
C2 0.086(3) 0.0528(14) 0.0469(13) 0.0074(11) 0.0004(17) -0.0087(19)
C3 0.0461(18) 0.0381(9) 0.0406(9) -0.0023(7) -0.0016(12) -0.0016(12)
C4 0.062(2) 0.0466(12) 0.0432(12) 0.0039(9) -0.0049(14) 0.0001(14)
C5 0.038(2) 0.0392(11) 0.0448(12) -0.0064(9) -0.0027(10) -0.0020(10)

_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 C5 1.752(3) . ?
Cl2 C5 1.766(3) . ?
Cl3 C5 1.757(3) . ?
N1 C1 1.462(3) . ?
N1 C3 1.469(3) . ?
N1 H1N 0.81(3) . ?
C1 C2 1.518(4) . ?
C1 H11 0.99(4) . ?
C1 H12 1.07(3) . ?
C2 H21 0.91(4) . ?
C2 H22 0.96(4) . ?
C2 H23 0.97(3) . ?
C3 C4 1.518(3) . ?
C3 H31 1.03(4) . ?
C3 H32 1.01(3) . ?
C4 H41 1.05(4) . ?
C4 H42 1.06(4) . ?
C4 H43 0.92(3) . ?
C5 H5 0.93(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
C1 N1 C3 112.42(16) . . ?
C1 N1 H1N 109(2) . . ?
C3 N1 H1N 106(2) . . ?
N1 C1 C2 110.88(19) . . ?
N1 C1 H11 111.3(19) . . ?
C2 C1 H11 105(2) . . ?
N1 C1 H12 105.7(16) . . ?
C2 C1 H12 110.0(17) . . ?
H11 C1 H12 114(2) . . ?
C1 C2 H21 113(3) . . ?
C1 C2 H22 108(2) . . ?
H21 C2 H22 103(3) . . ?
C1 C2 H23 111.9(18) . . ?
H21 C2 H23 99(3) . . ?
H22 C2 H23 121(3) . . ?
N1 C3 C4 110.64(18) . . ?
N1 C3 H31 107.9(19) . . ?
C4 C3 H31 110.6(18) . . ?
N1 C3 H32 105.2(19) . . ?
C4 C3 H32 113.9(18) . . ?
H31 C3 H32 108(2) . . ?
C3 C4 H41 111(2) . . ?
C3 C4 H42 109.8(18) . . ?
H41 C4 H42 105(2) . . ?
C3 C4 H43 111(2) . . ?
H41 C4 H43 109(3) . . ?
H42 C4 H43 111(3) . . ?
Cl1 C5 Cl3 111.05(16) . . ?
Cl1 C5 Cl2 109.20(14) . . ?
Cl3 C5 Cl2 110.10(15) . . ?
Cl1 C5 H5 107.6(17) . . ?
Cl3 C5 H5 107.1(17) . . ?
Cl2 C5 H5 111.7(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 N1 0.93(3) 2.26(3) 3.134(4) 156(2) .
N1 H1N Cl3 0.81(3) 3.03(3) 3.583(3) 127(3) 1_655
#==END

data_VI_SAD
_database_code_depnum_ccdc_archive 'CCDC 741278'

_audit_creation_method           SHELXL-97
_chemical_formula_moiety         'C H Cl3'
_chemical_formula_sum            'C H Cl3'
_chemical_formula_weight         119.37
_chemical_melting_point          -64
_chemical_name_common            trichloromethane
_chemical_name_systematic        trichloromethane
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_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_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4422(6)
_cell_length_b                   9.4578(7)
_cell_length_c                   5.8025(4)
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_cell_volume                     408.42(5)
_exptl_absorpt_coefficient_mu    2.004
_exptl_absorpt_correction_T_max  0.6468
_exptl_absorpt_correction_T_min  0.4379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.0286 before and 0.0150 after correction.
The Ratio of minimum to maximum transmission is 0.677025355597.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_F_000             232
_exptl_crystal_colour            less
_exptl_crystal_density_diffrn    1.941
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           ?
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2989
_diffrn_reflns_theta_full        33.11
_diffrn_reflns_theta_max         33.11
_diffrn_reflns_theta_min         4.12
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           25.0
_diffrn_source_power             1.125
_diffrn_source_target            Mo
_diffrn_source_voltage           45.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                733
_reflns_number_total             776
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    
;
Olex2, Durham University (compiled Mar 6 2009 16:11:20)
;
_computing_publication_material  
;
Olex2, Durham University (compiled Mar 6 2009 16:11:20)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.045
_refine_ls_R_factor_all          0.0188
_refine_ls_R_factor_gt           0.0172
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     25
_refine_ls_number_reflns         776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.0483
_refine_ls_wR_factor_ref         0.0494
_refine_ls_weighting_details     
;
calc w=1/[σ²(Fo²)+(0.0300P)²+0.0500P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_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.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.31322(3) 0.40223(2) 0.14097(4) 0.03150(8) Uani 1 1 d . . .
Cl2 Cl 0.39393(4) 0.2500 -0.28111(5) 0.02944(9) Uani 1 2 d S . .
C1 C 0.41244(14) 0.2500 0.02105(19) 0.02233(18) Uani 1 2 d S . .
H1 H 0.534(2) 0.2500 0.058(3) 0.027(4) 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 0.04179(14) 0.02353(11) 0.02917(14) -0.00252(6) 0.00783(7) -0.00039(7)
Cl2 0.02755(14) 0.04325(17) 0.01753(15) 0.000 0.00171(8) 0.000
C1 0.0214(4) 0.0260(4) 0.0196(5) 0.000 0.0003(3) 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
Cl1 C1 1.7613(7) . ?
Cl2 C1 1.7587(12) . ?
C1 Cl1 1.7613(7) 7_565 ?
C1 H1 0.927(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
Cl2 C1 Cl1 111.16(4) . 7_565 ?
Cl2 C1 Cl1 111.16(4) . . ?
Cl1 C1 Cl1 109.65(6) 7_565 . ?
Cl2 C1 H1 107.7(10) . . ?
Cl1 C1 H1 108.5(5) 7_565 . ?
Cl1 C1 H1 108.5(5) . . ?


