# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

data_General

_publ_contact_author_name        'Kohtaro Osakada'
_publ_contact_author_email       kosakada@res.titech.ac.jp
_publ_contact_author_fax         +81-45-924-5224
_publ_contact_author_phone       +81-45-924-5224
_publ_requested_journal          'Dalton Transactions'

loop_
_publ_author_name
'Yuji Suzaki'
'Takashi Saito'
'Tomohito Ide'
'Kohtaro Osakada'

_publ_author_address             
;
Chemical Resources Laboratory, Tokyo Institute of Technology, 
4259 Nagatsuta, Midori-ku, Yokohama 226-8503 JAPAN
;

_publ_section_title              
;
Rhomboid-shaped Organic Host Molecule with Small Binding Space. 
Unsymmetrical and Symmetrical Inclusion of Halonium Ions
;

#==============================================================================

data_cpeb(Cmce)

#==============================================================================

_audit_creation_method           'by CrystalStructure 4.0'

# CHEMICAL DATA

_chemical_formula_sum            'C30 H14 N2'
_chemical_formula_moiety         'C30 H14 N2'
_chemical_formula_weight         402.45
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'C m c e'
_symmetry_space_group_name_Hall  '-C 2bc 2'
_symmetry_Int_Tables_number      64
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,+Z
3 +X,1/2-Y,1/2+Z
4 -X,1/2-Y,1/2+Z
5 -X,-Y,-Z
6 +X,-Y,-Z
7 -X,1/2+Y,1/2-Z
8 +X,1/2+Y,1/2-Z
9 1/2+X,1/2+Y,+Z
10 1/2-X,1/2+Y,+Z
11 1/2+X,-Y,1/2+Z
12 1/2-X,-Y,1/2+Z
13 1/2-X,1/2-Y,-Z
14 1/2+X,1/2-Y,-Z
15 1/2-X,+Y,1/2-Z
16 1/2+X,+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   20.274(8)
_cell_length_b                   10.916(4)
_cell_length_c                   9.670(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2140.3(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2074
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      27.46
_cell_measurement_temperature    113
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832.00
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      113
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            5705
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1225
_reflns_number_gt                609
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1395
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1225
_refine_ls_number_parameters     76
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0708P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.170
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5000 0.16614(18) 0.1195(2) 0.0277(6) Uani 1.0 8 d . . .
C1 C 0.15359(11) 0.05416(16) 0.0377(3) 0.0356(6) Uani 1.0 16 d . . .
C2 C 0.21284(10) 0.10783(17) 0.0753(2) 0.0338(6) Uani 1.0 16 d . . .
C3 C 0.27256(11) 0.05498(16) 0.0389(2) 0.0315(6) Uani 1.0 16 d . . .
C4 C 0.33334(11) 0.11110(16) 0.0797(2) 0.0319(6) Uani 1.0 16 d . . .
C5 C 0.38348(11) 0.16056(17) 0.1162(2) 0.0311(6) Uani 1.0 16 d . . .
C6 C 0.44306(11) 0.21830(16) 0.16251(18) 0.0282(5) Uani 1.0 16 d . . .
C7 C 0.44113(11) 0.32104(15) 0.24835(19) 0.0323(5) Uani 1.0 16 d . . .
C8 C 0.5000 0.3724(2) 0.2919(3) 0.0349(8) Uani 1.0 8 d . . .
H1 H 0.1130 0.0913 0.0635 0.0428 Uiso 1.0 16 calc R . .
H2 H 0.2126 0.1820 0.1268 0.0405 Uiso 1.0 16 calc R . .
H7 H 0.4001 0.3551 0.2764 0.0388 Uiso 1.0 16 calc R . .
H8 H 0.5000 0.4419 0.3510 0.0419 Uiso 1.0 8 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2002 (Burla, et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
N1 C6 1.353(3) no . .
N1 C6 1.353(3) no . 2_655
C1 C1 1.390(3) no . 6_555
C1 C2 1.385(3) no . .
C2 C3 1.387(3) no . .
C3 C3 1.416(3) no . 6_555
C3 C4 1.432(3) no . .
C4 C5 1.204(3) no . .
C5 C6 1.434(3) no . .
C6 C7 1.396(3) no . .
C7 C8 1.384(3) no . .
C1 H1 0.950 no . .
C2 H2 0.950 no . .
C7 H7 0.950 no . .
C8 H8 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C6 N1 C6 117.17(19) no . . 2_655
C1 C1 C2 119.8(2) no 6_555 . .
C1 C2 C3 120.98(18) no . . .
C2 C3 C3 119.2(2) no . . 6_555
C2 C3 C4 120.23(17) no . . .
C3 C3 C4 120.60(19) no 6_555 . .
C3 C4 C5 178.2(2) no . . .
C4 C5 C6 178.8(2) no . . .
N1 C6 C5 115.97(17) no . . .
N1 C6 C7 123.0(2) no . . .
C5 C6 C7 121.0(2) no . . .
C6 C7 C8 118.8(2) no . . .
C7 C8 C7 119.1(2) no . . 2_655
C1 C1 H1 120.073 no 6_555 . .
C2 C1 H1 120.078 no . . .
C1 C2 H2 119.519 no . . .
C3 C2 H2 119.503 no . . .
C6 C7 H7 120.589 no . . .
C8 C7 H7 120.583 no . . .
C7 C8 H8 120.435 no . . .
C7 C8 H8 120.435 no 2_655 . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 N1 C6 C5 179.53(15) no . . 2_655 2_655
C6 N1 C6 C7 0.4(3) no . . 2_655 2_655
C6 N1 C6 C5 -179.53(15) no 2_655 . . .
C6 N1 C6 C7 -0.4(3) no 2_655 . . .
C1 C1 C2 C3 -0.1(3) no 6_555 . . .
C2 C1 C1 C2 -0.1(3) no . . 6_555 6_555
C1 C2 C3 C3 0.5(3) no . . . 6_555
C1 C2 C3 C4 -179.40(16) no . . . .
C2 C3 C3 C2 -0.7(3) no . . 6_555 6_555
C2 C3 C3 C4 179.19(16) no . . 6_555 6_555
C4 C3 C3 C2 179.19(16) no . . 6_555 6_555
C4 C3 C3 C4 -0.9(3) no . . 6_555 6_555
N1 C6 C7 C8 -0.0(3) no . . . .
C5 C6 C7 C8 179.05(15) no . . . .
C6 C7 C8 C7 0.5(3) no . . . 2_655
_database_code_depnum_ccdc_archive 'CCDC 973075'
data_General

_publ_contact_author_name        'Kohtaro Osakada'
_publ_contact_author_email       kosakada@res.titech.ac.jp
_publ_contact_author_fax         +81-45-924-5224
_publ_contact_author_phone       +81-45-924-5224
_publ_requested_journal          'Dalton Transactions'

loop_
_publ_author_name
'Yuji Suzaki'
'Takashi Saito'
'Tomohito Ide'
'Kohtaro Osakada'

_publ_author_address             
;
Chemical Resources Laboratory, Tokyo Institute of Technology, 
4259 Nagatsuta, Midori-ku, Yokohama 226-8503 JAPAN
;

_publ_section_title              
;
Rhomboid-shaped Organic Host Molecule with Small Binding Space. 
Unsymmetrical and Symmetrical Inclusion of Halonium Ions
;


#==============================================================================
data_cpeb(Pbca)

#==============================================================================

_audit_creation_method           'by CrystalStructure 4.0'

# CHEMICAL DATA

_chemical_formula_sum            'C15 H7 N'
_chemical_formula_moiety         'C15 H7 N'
_chemical_formula_weight         201.23
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,1/2-Y,1/2+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,1/2+Y,1/2-Z
8 1/2+X,+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.259(3)
_cell_length_b                   24.773(8)
_cell_length_c                   11.352(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2041.4(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5689
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      27.48
_cell_measurement_temperature    113
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832.00
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_T_max  0.985

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      113
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            14739
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using reflections with F² > 3.0 sigma(F²).
    The weighted     R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 3.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2333
_reflns_number_gt                1704
_reflns_threshold_expression     F²>3.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1165
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1704
_refine_ls_number_parameters     152
_refine_ls_goodness_of_fit_ref   1.279
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[0.0010Fo² + 1.0000σ(Fo²)]/(4Fo²)'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.36096(18) 0.98683(5) 0.33528(11) 0.0210(4) Uani 1.0 8 d . . .
C1 C 0.5846(3) 0.92177(6) 0.71498(14) 0.0228(4) Uani 1.0 8 d . . .
C2 C 0.5359(3) 0.87744(6) 0.68639(13) 0.0222(4) Uani 1.0 8 d . . .
C3 C 0.4792(2) 0.82434(6) 0.65190(13) 0.0195(4) Uani 1.0 8 d . . .
C4 C 0.5103(2) 0.78032(6) 0.72610(14) 0.0229(4) Uani 1.0 8 d . . .
C5 C 0.4613(3) 0.72849(6) 0.69273(14) 0.0249(5) Uani 1.0 8 d . . .
C6 C 0.3797(3) 0.71989(6) 0.58366(14) 0.0253(5) Uani 1.0 8 d . . .
C7 C 0.3446(3) 0.76289(6) 0.50965(14) 0.0221(4) Uani 1.0 8 d . . .
C8 C 0.3927(3) 0.81555(6) 0.54181(13) 0.0206(4) Uani 1.0 8 d . . .
C9 C 0.3584(2) 0.85934(6) 0.46185(13) 0.0216(4) Uani 1.0 8 d . . .
C10 C 0.3330(2) 0.89490(6) 0.39237(13) 0.0215(4) Uani 1.0 8 d . . .
C11 C 0.3196(2) 0.93604(6) 0.30265(13) 0.0197(4) Uani 1.0 8 d . . .
C12 C 0.2750(3) 0.92161(6) 0.18741(14) 0.0231(4) Uani 1.0 8 d . . .
C13 C 0.2773(3) 0.96115(7) 0.10084(14) 0.0262(5) Uani 1.0 8 d . . .
C14 C 0.3252(2) 1.01299(6) 0.13160(14) 0.0239(4) Uani 1.0 8 d . . .
C15 C 0.3647(2) 1.02440(6) 0.24927(13) 0.0203(4) Uani 1.0 8 d . . .
H1 H 0.5648 0.7862 0.7991 0.0278 Uiso 1.0 8 calc R . .
H2 H 0.4840 0.6995 0.7428 0.0298 Uiso 1.0 8 calc R . .
H3 H 0.3474 0.6851 0.5606 0.0305 Uiso 1.0 8 calc R . .
H4 H 0.2889 0.7568 0.4371 0.0264 Uiso 1.0 8 calc R . .
H5 H 0.2449 0.8861 0.1691 0.0277 Uiso 1.0 8 calc R . .
H6 H 0.2458 0.9527 0.0236 0.0317 Uiso 1.0 8 calc R . .
H7 H 0.3320 1.0399 0.0747 0.0287 Uiso 1.0 8 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
N1 C11 1.346(2) no . .
N1 C15 1.349(2) no . .
C1 C2 1.198(3) no . .
C1 C15 1.442(3) no . 5_676
C2 C3 1.433(3) no . .
C3 C4 1.396(3) no . .
C3 C8 1.415(3) no . .
C4 C5 1.385(3) no . .
C5 C6 1.389(3) no . .
C6 C7 1.380(3) no . .
C7 C8 1.399(3) no . .
C8 C9 1.436(3) no . .
C9 C10 1.197(3) no . .
C10 C11 1.444(3) no . .
C11 C12 1.394(3) no . .
C12 C13 1.388(3) no . .
C13 C14 1.376(3) no . .
C14 C15 1.395(3) no . .
C4 H1 0.930 no . .
C5 H2 0.930 no . .
C6 H3 0.930 no . .
C7 H4 0.930 no . .
C12 H5 0.930 no . .
C13 H6 0.930 no . .
C14 H7 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C11 N1 C15 116.77(13) no . . .
C2 C1 C15 177.60(17) no . . 5_676
C1 C2 C3 179.53(17) no . . .
C2 C3 C4 120.37(14) no . . .
C2 C3 C8 120.66(14) no . . .
C4 C3 C8 118.97(14) no . . .
C3 C4 C5 121.15(15) no . . .
C4 C5 C6 119.70(15) no . . .
C5 C6 C7 120.19(14) no . . .
C6 C7 C8 120.97(15) no . . .
C3 C8 C7 118.99(14) no . . .
C3 C8 C9 121.25(14) no . . .
C7 C8 C9 119.74(14) no . . .
C8 C9 C10 177.80(16) no . . .
C9 C10 C11 174.10(17) no . . .
N1 C11 C10 116.79(14) no . . .
N1 C11 C12 123.36(14) no . . .
C10 C11 C12 119.76(14) no . . .
C11 C12 C13 118.73(15) no . . .
C12 C13 C14 118.84(15) no . . .
C13 C14 C15 118.96(15) no . . .
N1 C15 C1 116.07(14) no . . 5_676
N1 C15 C14 123.30(14) no . . .
C1 C15 C14 120.62(14) no 5_676 . .
C3 C4 H1 118.967 no . . .
C5 C4 H1 119.881 no . . .
C4 C5 H2 120.167 no . . .
C6 C5 H2 120.129 no . . .
C5 C6 H3 120.003 no . . .
C7 C6 H3 119.799 no . . .
C6 C7 H4 119.664 no . . .
C8 C7 H4 119.360 no . . .
C11 C12 H5 120.449 no . . .
C13 C12 H5 120.822 no . . .
C12 C13 H6 120.379 no . . .
C14 C13 H6 120.777 no . . .
C13 C14 H7 120.471 no . . .
C15 C14 H7 120.570 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C11 N1 C15 C1 -177.95(12) no . . . 5_676
C11 N1 C15 C14 1.1(2) no . . . .
C15 N1 C11 C10 174.16(12) no . . . .
C15 N1 C11 C12 -2.4(2) no . . . .
C2 C3 C4 C5 -178.08(13) no . . . .
C2 C3 C8 C7 177.98(13) no . . . .
C2 C3 C8 C9 -0.3(3) no . . . .
C4 C3 C8 C7 -1.3(3) no . . . .
C4 C3 C8 C9 -179.62(13) no . . . .
C8 C3 C4 C5 1.2(3) no . . . .
C3 C4 C5 C6 0.0(3) no . . . .
C4 C5 C6 C7 -1.1(3) no . . . .
C5 C6 C7 C8 1.0(3) no . . . .
C6 C7 C8 C3 0.2(3) no . . . .
C6 C7 C8 C9 178.55(14) no . . . .
N1 C11 C12 C13 1.6(3) no . . . .
C10 C11 C12 C13 -174.90(13) no . . . .
C11 C12 C13 C14 0.6(3) no . . . .
C12 C13 C14 C15 -1.8(3) no . . . .
C13 C14 C15 N1 0.9(3) no . . . .
C13 C14 C15 C1 -180.00(13) no . . . 5_676
_database_code_depnum_ccdc_archive 'CCDC 973076'
data_General

_publ_contact_author_name        'Kohtaro Osakada'
_publ_contact_author_email       kosakada@res.titech.ac.jp
_publ_contact_author_fax         +81-45-924-5224
_publ_contact_author_phone       +81-45-924-5224
_publ_requested_journal          'Dalton Transactions'

loop_
_publ_author_name
'Yuji Suzaki'
'Takashi Saito'
'Tomohito Ide'
'Kohtaro Osakada'

_publ_author_address             
;
Chemical Resources Laboratory, Tokyo Institute of Technology, 
4259 Nagatsuta, Midori-ku, Yokohama 226-8503 JAPAN
;

_publ_section_title              
;
Rhomboid-shaped Organic Host Molecule with Small Binding Space. 
Unsymmetrical and Symmetrical Inclusion of Halonium Ions
;


#==============================================================================
data_Pd(OCOCF3)2(cpeb)

#==============================================================================

_audit_creation_method           SHELXL-2013

_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H14 F6 N2 O4 Pd'
_chemical_formula_sum            'C34 H14 F6 N2 O4 Pd'
_chemical_formula_weight         734.87

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.376(3)
_cell_length_b                   9.605(5)
_cell_length_c                   10.808(5)
_cell_angle_alpha                73.922(7)
_cell_angle_beta                 89.198(6)
_cell_angle_gamma                78.763(6)
_cell_volume                     721.0(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    2203
_cell_measurement_theta_min      2.2481
_cell_measurement_theta_max      28.1383

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.726
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  0.957


_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_reflns_number            3438
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.963
_diffrn_reflns_theta_max         25.015
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             2493
_reflns_number_gt                2363
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEXII'
_computing_cell_refinement       'Bruker APEXII'
_computing_data_reduction        'Bruker APEXII'
_computing_structure_solution    'SHELXT (George Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker XShell'
_computing_publication_material  'Bruker XShell'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2493
_refine_ls_number_parameters     214
_refine_ls_number_restraints     59
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_restrained_S_all      0.859
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd01 Pd 0.0000 0.5000 1.0000 0.01106(16) Uani 1 2 d S U P . .
O001 O -0.0675(3) 0.6143(3) 0.8147(2) 0.0154(5) Uani 1 1 d . U . . .
F1 F -0.0994(3) 0.7441(3) 0.5681(2) 0.0336(6) Uani 1 1 d . U . . .
F3 F -0.3277(3) 0.9017(3) 0.6014(2) 0.0392(7) Uani 1 1 d . U . . .
O002 O -0.2200(3) 0.8210(3) 0.8590(2) 0.0199(6) Uani 1 1 d . U . . .
N001 N -0.1272(4) 0.3378(3) 0.9790(3) 0.0115(6) Uani 1 1 d . U . . .
F2 F -0.0504(4) 0.9309(3) 0.6257(3) 0.0476(7) Uani 1 1 d . U . . .
C00P C 0.4940(4) 0.4355(4) 0.7245(3) 0.0139(7) Uani 1 1 d . U . . .
C00R C -0.2799(4) 0.3092(4) 1.0456(3) 0.0142(7) Uani 1 1 d . U . . .
C00A C -0.1370(5) 0.1358(4) 0.8906(3) 0.0142(7) Uani 1 1 d . U . . .
H00A H -0.0862 0.0776 0.8356 0.017 Uiso 1 1 calc R U . . .
C00B C 0.4185(4) 0.5257(4) 0.8055(3) 0.0150(7) Uani 1 1 d . U . . .
C00C C -0.2923(5) 0.1063(4) 0.9597(4) 0.0162(7) Uani 1 1 d . U . . .
H00C H -0.3475 0.0267 0.9538 0.019 Uiso 1 1 calc R U . . .
C00D C -0.1510(4) 0.7471(4) 0.7887(3) 0.0141(7) Uani 1 1 d . U . . .
C00E C 0.4078(4) 0.3220(4) 0.7102(3) 0.0153(7) Uani 1 1 d . U . . .
C00F C -0.0569(4) 0.2509(4) 0.9028(3) 0.0137(7) Uani 1 1 d . U . . .
C00G C 0.3523(4) 0.5976(4) 0.8746(3) 0.0138(7) Uani 1 1 d . U . . .
C00H C -0.3649(4) 0.1945(4) 1.0368(4) 0.0173(8) Uani 1 1 d . U . . .
H00H H -0.4721 0.1772 1.0837 0.021 Uiso 1 1 calc R U . . .
C00I C 0.2428(5) 0.2964(4) 0.7778(3) 0.0153(7) Uani 1 1 d . U . . .
C00J C 0.4828(5) 0.2343(4) 0.6316(3) 0.0170(7) Uani 1 1 d . U . . .
H00J H 0.4260 0.1565 0.6233 0.020 Uiso 1 1 calc R U . . .
C00K C 0.7257(5) 0.3736(4) 0.5788(4) 0.0197(8) Uani 1 1 d . U . . .
H00K H 0.8338 0.3912 0.5333 0.024 Uiso 1 1 calc R U . . .
C00L C 0.6410(5) 0.2610(4) 0.5652(4) 0.0200(8) Uani 1 1 d . U . . .
H00L H 0.6913 0.2022 0.5105 0.024 Uiso 1 1 calc R U . . .
C00M C 0.1069(4) 0.2807(4) 0.8355(3) 0.0135(7) Uani 1 1 d . U . . .
C00N C 0.6541(5) 0.4602(4) 0.6578(3) 0.0171(7) Uani 1 1 d . U . . .
H00N H 0.7134 0.5364 0.6668 0.020 Uiso 1 1 calc R U . . .
C00O C -0.1567(5) 0.8306(4) 0.6436(4) 0.0233(8) Uani 1 1 d . U . . .


_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
Pd01 O001 2.015(3) . no
Pd01 O001 2.015(3) 2_567 no
Pd01 N001 2.032(3) 2_567 no
Pd01 N001 2.032(3) . no
O001 C00D 1.260(4) . no
F1 C00O 1.328(4) . no
F3 C00O 1.331(5) . no
O002 C00D 1.219(4) . no
N001 C00F 1.358(4) . no
N001 C00R 1.361(4) . no
F2 C00O 1.329(5) . no
C00P C00N 1.400(5) . no
C00P C00E 1.408(5) . no
C00P C00B 1.430(5) . no
C00R C00H 1.394(5) . no
C00R C00G 1.435(5) 2_567 no
C00A C00F 1.389(5) . no
C00A C00C 1.391(5) . no
C00A H00A 0.9500 . no
C00B C00G 1.191(5) . no
C00C C00H 1.379(5) . no
C00C H00C 0.9500 . no
C00D C00O 1.548(5) . no
C00E C00J 1.393(5) . no
C00E C00I 1.438(5) . no
C00F C00M 1.437(5) . no
C00G C00R 1.435(5) 2_567 no
C00H H00H 0.9500 . no
C00I C00M 1.186(5) . ?
C00J C00L 1.390(5) . ?
C00J H00J 0.9500 . ?
C00K C00N 1.381(5) . ?
C00K C00L 1.391(5) . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00N H00N 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O001 Pd01 O001 180.00(14) . 2_567 no
O001 Pd01 N001 89.78(11) . 2_567 no
O001 Pd01 N001 90.22(11) 2_567 2_567 no
O001 Pd01 N001 90.22(11) . . no
O001 Pd01 N001 89.78(11) 2_567 . no
N001 Pd01 N001 180.0 2_567 . no
C00D O001 Pd01 119.2(2) . . no
C00F N001 C00R 118.3(3) . . no
C00F N001 Pd01 120.8(2) . . no
C00R N001 Pd01 120.8(2) . . no
C00N C00P C00E 119.3(3) . . no
C00N C00P C00B 120.1(3) . . no
C00E C00P C00B 120.5(3) . . no
N001 C00R C00H 121.8(3) . . no
N001 C00R C00G 117.5(3) . 2_567 no
C00H C00R C00G 120.7(3) . 2_567 no
C00F C00A C00C 119.4(3) . . no
C00F C00A H00A 120.3 . . no
C00C C00A H00A 120.3 . . no
C00G C00B C00P 178.0(4) . . no
C00H C00C C00A 118.9(3) . . no
C00H C00C H00C 120.6 . . no
C00A C00C H00C 120.6 . . no
O002 C00D O001 130.8(3) . . no
O002 C00D C00O 115.6(3) . . no
O001 C00D C00O 113.6(3) . . no
C00J C00E C00P 120.1(3) . . no
C00J C00E C00I 120.1(3) . . no
C00P C00E C00I 119.7(3) . . no
N001 C00F C00A 122.0(3) . . no
N001 C00F C00M 117.6(3) . . no
C00A C00F C00M 120.5(3) . . no
C00B C00G C00R 176.4(4) . 2_567 no
C00C C00H C00R 119.6(3) . . no
C00C C00H H00H 120.2 . . no
C00R C00H H00H 120.2 . . no
C00M C00I C00E 177.0(4) . . no
C00L C00J C00E 119.8(3) . . no
C00L C00J H00J 120.1 . . no
C00E C00J H00J 120.1 . . no
C00N C00K C00L 120.7(3) . . no
C00N C00K H00K 119.6 . . no
C00L C00K H00K 119.6 . . no
C00J C00L C00K 120.0(3) . . no
C00J C00L H00L 120.0 . . no
C00K C00L H00L 120.0 . . no
C00I C00M C00F 175.4(4) . . no
C00K C00N C00P 119.9(3) . . no
C00K C00N H00N 120.0 . . no
C00P C00N H00N 120.0 . . no
F1 C00O F2 107.9(3) . . no
F1 C00O F3 106.6(3) . . no
F2 C00O F3 107.6(3) . . no
F1 C00O C00D 114.1(3) . . no
F2 C00O C00D 109.3(3) . . no
F3 C00O C00D 111.2(3) . . no

_refine_diff_density_max         1.215
_refine_diff_density_min         -1.301
_refine_diff_density_rms         0.109

_shelxl_version_number           2013-4

#     End of CIF
_database_code_depnum_ccdc_archive 'CCDC 973077'
