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

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
lithium phthalocyanine 
;
_chemical_name_common            'lithium phthalocyanine'
_chemical_melting_point          400K
_chemical_formula_moiety         'C32 H16 Li N8 '
_chemical_formula_sum            'C32 H16 Li N8'
_chemical_formula_weight         519.47

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'
Li Li -0.0003 0.0001 '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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 4/m c c'
_symmetry_space_group_name_Hall  '-P 4 2c'
_symmetry_Int_Tables_number      124

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

_cell_length_a                   13.852(4)
_cell_length_b                   13.852(4)
_cell_length_c                   6.4216(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1232.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2820
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.4

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      1.40
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             534
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'


_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            9032
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         27.50
_reflns_number_total             775
_reflns_number_gt                692
_reflns_threshold_expression     >2sigma(I)

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep-3

_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)+(0.0541P)²+0.3795P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         775
_refine_ls_number_parameters     64
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
N1 N 0.37295(9) 0.56074(9) 0.5000 0.0219(3) Uani 1 2 d S . .
N2 N 0.41893(10) 0.72974(9) 0.5000 0.0234(4) Uani 1 2 d S . .
C1 C 0.35493(11) 0.65761(11) 0.5000 0.0226(4) Uani 1 2 d S . .
C2 C 0.28678(11) 0.51442(12) 0.5000 0.0229(4) Uani 1 2 d S . .
C3 C 0.20679(11) 0.58495(12) 0.5000 0.0251(4) Uani 1 2 d S . .
C4 C 0.24994(11) 0.67559(12) 0.5000 0.0252(4) Uani 1 2 d S . .
C5 C 0.19487(13) 0.75950(13) 0.5000 0.0325(4) Uani 1 2 d S . .
H1 H 0.2241 0.8216 0.5000 0.039 Uiso 1 2 calc SR . .
C6 C 0.09493(15) 0.74840(15) 0.5000 0.0408(5) Uani 1 2 d S . .
H2 H 0.0551 0.8042 0.5000 0.049 Uiso 1 2 calc SR . .
C7 C 0.05212(13) 0.65770(15) 0.5000 0.0417(5) Uani 1 2 d S . .
H3 H -0.0163 0.6527 0.5000 0.050 Uiso 1 2 calc SR . .
C8 C 0.10781(12) 0.57399(15) 0.5000 0.0343(5) Uani 1 2 d S . .
H4 H 0.0788 0.5118 0.5000 0.041 Uiso 1 2 calc SR . .
Li1 Li 0.5000 0.5000 0.5000 0.0297(12) Uani 1 8 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
N1 0.0196(7) 0.0182(7) 0.0280(7) 0.000 0.000 -0.0003(5)
N2 0.0235(7) 0.0190(7) 0.0276(7) 0.000 0.000 0.0020(5)
C1 0.0218(8) 0.0229(8) 0.0232(7) 0.000 0.000 0.0037(6)
C2 0.0176(7) 0.0267(9) 0.0242(8) 0.000 0.000 0.0009(6)
C3 0.0203(8) 0.0293(9) 0.0258(8) 0.000 0.000 0.0042(6)
C4 0.0229(8) 0.0295(9) 0.0232(7) 0.000 0.000 0.0054(6)
C5 0.0318(10) 0.0310(9) 0.0347(9) 0.000 0.000 0.0099(7)
C6 0.0316(10) 0.0435(11) 0.0472(12) 0.000 0.000 0.0190(8)
C7 0.0199(9) 0.0523(13) 0.0528(13) 0.000 0.000 0.0102(8)
C8 0.0199(8) 0.0418(10) 0.0412(10) 0.000 0.000 0.0028(7)
Li1 0.0203(15) 0.0203(15) 0.048(3) 0.000 0.000 0.000

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.355(2) . ?
N1 C1 1.3648(19) . ?
N1 Li1 1.9507(14) . ?
N2 C1 1.336(2) . ?
N2 C2 1.342(2) 10_566 ?
C1 C4 1.475(2) . ?
C2 N2 1.342(2) 2_655 ?
C2 C3 1.477(2) . ?
C3 C8 1.379(2) . ?
C3 C4 1.391(2) . ?
C4 C5 1.390(2) . ?
C5 C6 1.393(3) . ?
C5 H1 0.9500 . ?
C6 C7 1.389(3) . ?
C6 H2 0.9500 . ?
C7 C8 1.393(3) . ?
C7 H3 0.9500 . ?
C8 H4 0.9500 . ?
Li1 N1 1.9507(14) 10_566 ?
Li1 N1 1.9507(14) 2_655 ?
Li1 N1 1.9507(14) 9_666 ?
Li1 Li1 3.2108(9) 5_655 ?
Li1 Li1 3.2108(9) 5_654 ?

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 C1 107.72(13) . . ?
C2 N1 Li1 126.18(10) . . ?
C1 N1 Li1 126.09(11) . . ?
C1 N2 C2 121.76(13) . 10_566 ?
N2 C1 N1 127.88(14) . . ?
N2 C1 C4 121.87(13) . . ?
N1 C1 C4 110.25(14) . . ?
N2 C2 N1 128.08(14) 2_655 . ?
N2 C2 C3 121.58(14) 2_655 . ?
N1 C2 C3 110.34(14) . . ?
C8 C3 C4 121.77(16) . . ?
C8 C3 C2 132.28(16) . . ?
C4 C3 C2 105.94(13) . . ?
C5 C4 C3 121.27(15) . . ?
C5 C4 C1 132.99(16) . . ?
C3 C4 C1 105.74(13) . . ?
C4 C5 C6 116.93(17) . . ?
C4 C5 H1 121.5 . . ?
C6 C5 H1 121.5 . . ?
C7 C6 C5 121.61(17) . . ?
C7 C6 H2 119.2 . . ?
C5 C6 H2 119.2 . . ?
C6 C7 C8 121.10(17) . . ?
C6 C7 H3 119.5 . . ?
C8 C7 H3 119.5 . . ?
C3 C8 C7 117.32(18) . . ?
C3 C8 H4 121.3 . . ?
C7 C8 H4 121.3 . . ?
N1 Li1 N1 180.0 10_566 2_655 ?
N1 Li1 N1 90.0 10_566 9_666 ?
N1 Li1 N1 90.0 2_655 9_666 ?
N1 Li1 N1 90.0 10_566 . ?
N1 Li1 N1 90.0 2_655 . ?
N1 Li1 N1 180.0 9_666 . ?
N1 Li1 Li1 90.0 10_566 5_655 ?
N1 Li1 Li1 90.0 2_655 5_655 ?
N1 Li1 Li1 90.0 9_666 5_655 ?
N1 Li1 Li1 90.0 . 5_655 ?
N1 Li1 Li1 90.0 10_566 5_654 ?
N1 Li1 Li1 90.0 2_655 5_654 ?
N1 Li1 Li1 90.0 9_666 5_654 ?
N1 Li1 Li1 90.0 . 5_654 ?
Li1 Li1 Li1 180.0 5_655 5_654 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C1 N1 0.0 10_566 . . . ?
C2 N2 C1 C4 180.0 10_566 . . . ?
C2 N1 C1 N2 180.0 . . . . ?
Li1 N1 C1 N2 0.0 . . . . ?
C2 N1 C1 C4 0.0 . . . . ?
Li1 N1 C1 C4 180.0 . . . . ?
C1 N1 C2 N2 180.0 . . . 2_655 ?
Li1 N1 C2 N2 0.0 . . . 2_655 ?
C1 N1 C2 C3 0.0 . . . . ?
Li1 N1 C2 C3 180.0 . . . . ?
N2 C2 C3 C8 0.0 2_655 . . . ?
N1 C2 C3 C8 180.0 . . . . ?
N2 C2 C3 C4 180.0 2_655 . . . ?
N1 C2 C3 C4 0.0 . . . . ?
C8 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 C5 180.0 . . . . ?
C8 C3 C4 C1 180.0 . . . . ?
C2 C3 C4 C1 0.0 . . . . ?
N2 C1 C4 C5 0.0 . . . . ?
N1 C1 C4 C5 180.0 . . . . ?
N2 C1 C4 C3 180.0 . . . . ?
N1 C1 C4 C3 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C1 C4 C5 C6 180.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C4 C3 C8 C7 0.0 . . . . ?
C2 C3 C8 C7 180.0 . . . . ?
C6 C7 C8 C3 0.0 . . . . ?
C2 N1 Li1 N1 180.0 . . . 10_566 ?
C1 N1 Li1 N1 0.0 . . . 10_566 ?
C2 N1 Li1 N1 0.0 . . . 2_655 ?
C1 N1 Li1 N1 180.0 . . . 2_655 ?
C2 N1 Li1 N1 0(100) . . . 9_666 ?
C1 N1 Li1 N1 180(100) . . . 9_666 ?
C2 N1 Li1 Li1 -90.0 . . . 5_655 ?
C1 N1 Li1 Li1 90.0 . . . 5_655 ?
C2 N1 Li1 Li1 90.0 . . . 5_654 ?
C1 N1 Li1 Li1 -90.0 . . . 5_654 ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 979678'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_LiPcCl11

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
lithium phthalocyanine chloride 
;
_chemical_name_common            'lithium phthalocyanine chloride'
_chemical_melting_point          400K
_chemical_formula_moiety         'C32 H16 Cl0.11 Li N8'
_chemical_formula_sum            'C32 H16 Cl0.11 Li N8'
_chemical_formula_weight         523.38

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'
Li Li -0.0003 0.0001 '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           tetragonal
_symmetry_space_group_name_H-M   'P 4/m c c'
_symmetry_space_group_name_Hall  '-P 4 2c'
_symmetry_Int_Tables_number      124
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x, z'
'-x, -y, z'
'y, -x, z'
'-x, y, z+1/2'
'y, x, z+1/2'
'x, -y, z+1/2'
'-y, -x, z+1/2'
'-x, -y, -z'
'y, -x, -z'
'x, y, -z'
'-y, x, -z'
'x, -y, -z-1/2'
'-y, -x, -z-1/2'
'-x, y, -z-1/2'
'y, x, -z-1/2'

_cell_length_a                   13.8430(9)
_cell_length_b                   13.8430(9)
_cell_length_c                   6.4156(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1229.41(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2270
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      1.42
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             537.7
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            9062
_diffrn_reflns_av_R_equivalents  0.070
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         27.47
_reflns_number_total             774
_reflns_number_gt                635
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0474P)²+0.4863P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         774
_refine_ls_number_parameters     66
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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 1.0000 0.0000 0.2500 0.52(10) Uani 0.11 8 d SP . .
N1 N 0.62704(12) 0.43959(12) 0.0000 0.0249(5) Uani 1 2 d S . .
N2 N 0.58097(13) 0.27036(13) 0.0000 0.0263(5) Uani 1 2 d S . .
C1 C 0.64519(16) 0.34256(16) 0.0000 0.0255(5) Uani 1 2 d S . .
C2 C 0.71322(15) 0.48577(16) 0.0000 0.0258(5) Uani 1 2 d S . .
C3 C 0.79306(16) 0.41501(17) 0.0000 0.0277(5) Uani 1 2 d S . .
C4 C 0.74986(15) 0.32465(16) 0.0000 0.0271(5) Uani 1 2 d S . .
C5 C 0.80518(17) 0.24111(18) 0.0000 0.0362(6) Uani 1 2 d S . .
H1 H 0.7760 0.1790 0.0000 0.043 Uiso 1 2 calc SR . .
C6 C 0.90484(19) 0.2520(2) 0.0000 0.0441(7) Uani 1 2 d S . .
H2 H 0.9446 0.1961 0.0000 0.053 Uiso 1 2 calc SR . .
C7 C 0.94773(18) 0.3426(2) 0.0000 0.0444(7) Uani 1 2 d S . .
H3 H 1.0162 0.3477 0.0000 0.053 Uiso 1 2 calc SR . .
C8 C 0.89206(17) 0.42571(19) 0.0000 0.0375(6) Uani 1 2 d S . .
H4 H 0.9211 0.4879 0.0000 0.045 Uiso 1 2 calc SR . .
Li1 Li 0.5000 0.5000 0.0000 0.0335(18) Uani 1 8 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 0.24(3) 0.24(3) 1.1(3) 0.000 0.000 0.000
N1 0.0248(10) 0.0204(9) 0.0295(10) 0.000 0.000 -0.0006(7)
N2 0.0273(10) 0.0221(9) 0.0296(10) 0.000 0.000 0.0012(7)
C1 0.0249(11) 0.0276(12) 0.0240(11) 0.000 0.000 0.0038(8)
C2 0.0216(11) 0.0292(12) 0.0265(11) 0.000 0.000 0.0002(9)
C3 0.0234(11) 0.0338(13) 0.0258(12) 0.000 0.000 0.0047(9)
C4 0.0247(12) 0.0309(12) 0.0255(11) 0.000 0.000 0.0054(9)
C5 0.0342(14) 0.0360(14) 0.0386(13) 0.000 0.000 0.0108(10)
C6 0.0341(14) 0.0476(16) 0.0507(18) 0.000 0.000 0.0217(12)
C7 0.0229(13) 0.0532(17) 0.0571(18) 0.000 0.000 0.0104(11)
C8 0.0223(12) 0.0445(15) 0.0459(15) 0.000 0.000 0.0043(10)
Li1 0.025(2) 0.025(2) 0.050(5) 0.000 0.000 0.000

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.353(3) . ?
N1 C1 1.366(3) . ?
N1 Li1 1.9474(17) . ?
N2 C2 1.337(3) 10_565 ?
N2 C1 1.338(3) . ?
C1 C4 1.470(3) . ?
C2 N2 1.337(3) 2_655 ?
C2 C3 1.477(3) . ?
C3 C8 1.378(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.388(3) . ?
C6 C7 1.388(4) . ?
C7 C8 1.385(3) . ?
Li1 N1 1.9474(17) 10_565 ?
Li1 N1 1.9474(17) 2_655 ?
Li1 N1 1.9474(17) 9_665 ?
Li1 Li1 3.2078(3) 5_655 ?
Li1 Li1 3.2078(3) 5_654 ?

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 C1 107.60(18) . . ?
C2 N1 Li1 126.38(14) . . ?
C1 N1 Li1 126.03(14) . . ?
C2 N2 C1 121.86(18) 10_565 . ?
N2 C1 N1 127.8(2) . . ?
N2 C1 C4 121.94(19) . . ?
N1 C1 C4 110.30(19) . . ?
N2 C2 N1 128.0(2) 2_655 . ?
N2 C2 C3 121.8(2) 2_655 . ?
N1 C2 C3 110.26(19) . . ?
C8 C3 C4 121.7(2) . . ?
C8 C3 C2 132.3(2) . . ?
C4 C3 C2 106.00(19) . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 C1 105.84(18) . . ?
C5 C4 C1 133.2(2) . . ?
C4 C5 C6 117.3(2) . . ?
C7 C6 C5 121.5(2) . . ?
C8 C7 C6 120.9(2) . . ?
C3 C8 C7 117.7(2) . . ?
N1 Li1 N1 180.0 10_565 2_655 ?
N1 Li1 N1 90.0 10_565 . ?
N1 Li1 N1 90.0 2_655 . ?
N1 Li1 N1 90.0 10_565 9_665 ?
N1 Li1 N1 90.0 2_655 9_665 ?
N1 Li1 N1 180.00(4) . 9_665 ?
N1 Li1 Li1 90.0 10_565 5_655 ?
N1 Li1 Li1 90.0 2_655 5_655 ?
N1 Li1 Li1 90.0 . 5_655 ?
N1 Li1 Li1 90.0 9_665 5_655 ?
N1 Li1 Li1 90.0 10_565 5_654 ?
N1 Li1 Li1 90.0 2_655 5_654 ?
N1 Li1 Li1 90.0 . 5_654 ?
N1 Li1 Li1 90.0 9_665 5_654 ?
Li1 Li1 Li1 180.0 5_655 5_654 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 979679'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_LiPcCl020

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
lithium phthalocyanine chloride 
;
_chemical_name_common            'lithium phthalocyanine chloride'
_chemical_melting_point          400K
_chemical_formula_moiety         'C32 H16 Li Cl0.20 N8'
_chemical_formula_sum            'C32 H16 Cl0.20 Li N8'
_chemical_formula_weight         526.56

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'
Li Li -0.0003 0.0001 '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           tetragonal
_symmetry_space_group_name_H-M   'P 4/m c c'
_symmetry_space_group_name_Hall  '-P 4 2c'
_symmetry_Int_Tables_number      124


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

_cell_length_a                   13.829(5)
_cell_length_b                   13.829(5)
_cell_length_c                   6.406(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1225.1(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2553
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.4

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      1.42
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540.8
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            9057
_diffrn_reflns_av_R_equivalents  0.061
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         27.44
_reflns_number_total             771
_reflns_number_gt                653
_reflns_threshold_expression     >2sigma(I)

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3


_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)+(0.0524P)²+0.5215P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_number_reflns         771
_refine_ls_number_parameters     66
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.0000 1.0000 0.7500 0.213(12) Uani 0.20 8 d SP . .
N1 N 0.43926(11) 0.62718(12) 0.5000 0.0227(4) Uani 1 2 d S . .
N2 N 0.58095(13) 0.72996(12) 0.5000 0.0243(4) Uani 1 2 d S . .
C3 C 0.64531(15) 0.65788(15) 0.5000 0.0235(5) Uani 1 2 d S . .
C4 C 0.32445(15) 0.74998(15) 0.5000 0.0255(5) Uani 1 2 d S . .
C5 C 0.41490(16) 0.79319(15) 0.5000 0.0256(5) Uani 1 2 d S . .
C6 C 0.48567(15) 0.71357(14) 0.5000 0.0239(5) Uani 1 2 d S . .
C7 C 0.24068(17) 0.80529(16) 0.5000 0.0329(6) Uani 1 2 d S . .
H1 H 0.1785 0.7760 0.5000 0.039 Uiso 1 2 calc SR . .
C8 C 0.34221(18) 0.94803(17) 0.5000 0.0400(7) Uani 1 2 d S . .
H2 H 0.3473 1.0165 0.5000 0.048 Uiso 1 2 calc SR . .
C9 C 0.42583(18) 0.89226(16) 0.5000 0.0342(6) Uani 1 2 d S . .
H3 H 0.4881 0.9213 0.5000 0.041 Uiso 1 2 calc SR . .
C10 C 0.25152(19) 0.90533(18) 0.5000 0.0397(6) Uani 1 2 d S . .
H4 H 0.1956 0.9452 0.5000 0.048 Uiso 1 2 calc SR . .
Li11 Li 0.5000 0.5000 0.5000 0.0355(18) Uani 1 8 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 0.096(5) 0.096(5) 0.45(4) 0.000 0.000 0.000
N1 0.0193(9) 0.0223(9) 0.0266(9) 0.000 0.000 0.0000(7)
N2 0.0239(9) 0.0225(9) 0.0264(9) 0.000 0.000 -0.0023(7)
C3 0.0223(10) 0.0255(11) 0.0228(10) 0.000 0.000 -0.0024(8)
C4 0.0305(11) 0.0234(11) 0.0226(10) 0.000 0.000 0.0037(9)
C5 0.0299(11) 0.0222(11) 0.0248(11) 0.000 0.000 0.0040(8)
C6 0.0278(11) 0.0211(10) 0.0228(10) 0.000 0.000 -0.0004(8)
C7 0.0319(12) 0.0322(13) 0.0346(12) 0.000 0.000 0.0084(9)
C8 0.0469(15) 0.0218(11) 0.0514(16) 0.000 0.000 0.0075(10)
C9 0.0379(13) 0.0232(11) 0.0416(14) 0.000 0.000 0.0017(9)
C10 0.0414(14) 0.0304(13) 0.0473(16) 0.000 0.000 0.0167(11)
Li11 0.025(2) 0.025(2) 0.056(5) 0.000 0.000 0.000

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.356(3) . ?
N1 C3 1.367(3) 2_655 ?
N1 Li11 1.9490(18) . ?
N2 C3 1.336(3) . ?
N2 C6 1.337(3) . ?
C3 N1 1.367(3) 10_566 ?
C3 C4 1.468(3) 10_566 ?
C4 C5 1.386(3) . ?
C4 C7 1.388(3) . ?
C4 C3 1.468(3) 2_655 ?
C5 C9 1.378(3) . ?
C5 C6 1.473(3) . ?
C7 C10 1.392(3) . ?
C7 H1 0.9500 . ?
C8 C10 1.386(4) . ?
C8 C9 1.390(3) . ?
C8 H2 0.9500 . ?
C9 H3 0.9500 . ?
C10 H4 0.9500 . ?
Li11 N1 1.9490(18) 2_655 ?
Li11 N1 1.9490(18) 9_666 ?
Li11 N1 1.9490(18) 10_566 ?
Li11 Li11 3.2030(10) 5_655 ?
Li11 Li11 3.2030(10) 5_654 ?

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
C6 N1 C3 107.67(16) . 2_655 ?
C6 N1 Li11 126.23(13) . . ?
C3 N1 Li11 126.10(13) 2_655 . ?
C3 N2 C6 122.00(17) . . ?
N2 C3 N1 127.67(18) . 10_566 ?
N2 C3 C4 122.18(18) . 10_566 ?
N1 C3 C4 110.15(18) 10_566 10_566 ?
C5 C4 C7 121.03(19) . . ?
C5 C4 C3 105.95(18) . 2_655 ?
C7 C4 C3 133.0(2) . 2_655 ?
C9 C5 C4 121.8(2) . . ?
C9 C5 C6 132.1(2) . . ?
C4 C5 C6 106.10(18) . . ?
N2 C6 N1 128.01(19) . . ?
N2 C6 C5 121.87(18) . . ?
N1 C6 C5 110.12(18) . . ?
C4 C7 C10 117.2(2) . . ?
C4 C7 H1 121.4 . . ?
C10 C7 H1 121.4 . . ?
C10 C8 C9 121.1(2) . . ?
C10 C8 H2 119.5 . . ?
C9 C8 H2 119.5 . . ?
C5 C9 C8 117.4(2) . . ?
C5 C9 H3 121.3 . . ?
C8 C9 H3 121.3 . . ?
C8 C10 C7 121.4(2) . . ?
C8 C10 H4 119.3 . . ?
C7 C10 H4 119.3 . . ?
N1 Li11 N1 90.0 2_655 . ?
N1 Li11 N1 90.0 2_655 9_666 ?
N1 Li11 N1 180.0 . 9_666 ?
N1 Li11 N1 180.00(8) 2_655 10_566 ?
N1 Li11 N1 90.0 . 10_566 ?
N1 Li11 N1 90.0 9_666 10_566 ?
N1 Li11 Li11 90.0 2_655 5_655 ?
N1 Li11 Li11 90.0 . 5_655 ?
N1 Li11 Li11 90.0 9_666 5_655 ?
N1 Li11 Li11 90.0 10_566 5_655 ?
N1 Li11 Li11 90.0 2_655 5_654 ?
N1 Li11 Li11 90.0 . 5_654 ?
N1 Li11 Li11 90.0 9_666 5_654 ?
N1 Li11 Li11 90.0 10_566 5_654 ?
Li11 Li11 Li11 180.0 5_655 5_654 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 C3 N1 0.0 . . . 10_566 ?
C6 N2 C3 C4 180.0 . . . 10_566 ?
C7 C4 C5 C9 0.0 . . . . ?
C3 C4 C5 C9 180.0 2_655 . . . ?
C7 C4 C5 C6 180.0 . . . . ?
C3 C4 C5 C6 0.0 2_655 . . . ?
C3 N2 C6 N1 0.0 . . . . ?
C3 N2 C6 C5 180.0 . . . . ?
C3 N1 C6 N2 180.0 2_655 . . . ?
Li11 N1 C6 N2 0.0 . . . . ?
C3 N1 C6 C5 0.0 2_655 . . . ?
Li11 N1 C6 C5 180.0 . . . . ?
C9 C5 C6 N2 0.0 . . . . ?
C4 C5 C6 N2 180.0 . . . . ?
C9 C5 C6 N1 180.0 . . . . ?
C4 C5 C6 N1 0.0 . . . . ?
C5 C4 C7 C10 0.0 . . . . ?
C3 C4 C7 C10 180.0 2_655 . . . ?
C4 C5 C9 C8 0.0 . . . . ?
C6 C5 C9 C8 180.0 . . . . ?
C10 C8 C9 C5 0.0 . . . . ?
C9 C8 C10 C7 0.0 . . . . ?
C4 C7 C10 C8 0.0 . . . . ?
C6 N1 Li11 N1 180.0 . . . 2_655 ?
C3 N1 Li11 N1 0.0 2_655 . . 2_655 ?
C6 N1 Li11 N1 0.0 . . . 9_666 ?
C3 N1 Li11 N1 180.0 2_655 . . 9_666 ?
C6 N1 Li11 N1 0.0 . . . 10_566 ?
C3 N1 Li11 N1 180.0 2_655 . . 10_566 ?
C6 N1 Li11 Li11 90.0 . . . 5_655 ?
C3 N1 Li11 Li11 -90.0 2_655 . . 5_655 ?
C6 N1 Li11 Li11 -90.0 . . . 5_654 ?
C3 N1 Li11 Li11 90.0 2_655 . . 5_654 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 979680'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_LiPcCl021

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
lithium phthalocyanine chloride
;
_chemical_name_common            'lithium phthalocyanine chloride'
_chemical_melting_point          400K
_chemical_formula_moiety         'C32 H16 Cl0.21 Li N8 '
_chemical_formula_sum            'C32 H16 Cl0.21 Li N8'
_chemical_formula_weight         526.92

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'
Li Li -0.0003 0.0001 '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           tetragonal
_symmetry_space_group_name_H-M   'P 4/m c c'
_symmetry_space_group_name_Hall  '-P 4 2c'
_symmetry_Int_Tables_number      124

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

_cell_length_a                   13.864(6)
_cell_length_b                   13.864(6)
_cell_length_c                   6.414(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1232.8(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1831
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.2

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      1.42
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             541.14
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_T_max  0.9616
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            9014
_diffrn_reflns_av_R_equivalents  0.060

_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         27.46
_reflns_number_total             773
_reflns_number_gt                651
_reflns_threshold_expression     >2sigma(I)


_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3


_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)+(0.1215P)²+0.4048P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_number_reflns         773
_refine_ls_number_parameters     66
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.2126
_refine_ls_wR_factor_gt          0.1988
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_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 1.0000 1.0000 0.7500 0.30(2) Uani 0.21 8 d SP . .
N1 N 0.56047(15) 0.62691(17) 0.5000 0.0320(7) Uani 1 2 d S . .
N2 N 0.41905(18) 0.72952(17) 0.5000 0.0335(7) Uani 1 2 d S . .
C1 C 0.5142(2) 0.71309(19) 0.5000 0.0324(7) Uani 1 2 d S . .
C2 C 0.6576(2) 0.6449(2) 0.5000 0.0318(7) Uani 1 2 d S . .
C3 C 0.6751(2) 0.74947(19) 0.5000 0.0342(7) Uani 1 2 d S . .
C4 C 0.5847(2) 0.7928(2) 0.5000 0.0347(8) Uani 1 2 d S . .
C5 C 0.5738(2) 0.8917(2) 0.5000 0.0425(9) Uani 1 2 d S . .
H1 H 0.5118 0.9208 0.5000 0.051 Uiso 1 2 calc SR . .
C6 C 0.6576(3) 0.9470(2) 0.5000 0.0512(10) Uani 1 2 d S . .
H2 H 0.6525 1.0154 0.5000 0.061 Uiso 1 2 calc SR . .
C7 C 0.7479(3) 0.9050(3) 0.5000 0.0500(10) Uani 1 2 d S . .
H3 H 0.8036 0.9448 0.5000 0.060 Uiso 1 2 calc SR . .
C8 C 0.7586(2) 0.8052(2) 0.5000 0.0435(9) Uani 1 2 d S . .
H4 H 0.8207 0.7762 0.5000 0.052 Uiso 1 2 calc SR . .
Li1 Li 0.5000 0.5000 0.5000 0.043(2) Uani 1 8 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 0.092(7) 0.092(7) 0.71(7) 0.000 0.000 0.000
N1 0.0253(12) 0.0288(13) 0.0418(14) 0.000 0.000 -0.0001(9)
N2 0.0304(13) 0.0277(12) 0.0425(14) 0.000 0.000 0.0001(9)
C1 0.0310(16) 0.0255(14) 0.0408(15) 0.000 0.000 -0.0004(11)
C2 0.0301(14) 0.0289(15) 0.0363(15) 0.000 0.000 -0.0018(10)
C3 0.0360(16) 0.0278(15) 0.0389(15) 0.000 0.000 -0.0062(11)
C4 0.0366(16) 0.0262(15) 0.0412(16) 0.000 0.000 -0.0026(11)
C5 0.0441(18) 0.0265(15) 0.057(2) 0.000 0.000 -0.0048(12)
C6 0.055(2) 0.0275(16) 0.071(2) 0.000 0.000 -0.0091(14)
C7 0.048(2) 0.0378(19) 0.065(2) 0.000 0.000 -0.0180(14)
C8 0.0378(18) 0.0412(19) 0.0513(19) 0.000 0.000 -0.0101(12)
Li1 0.030(3) 0.030(3) 0.067(7) 0.000 0.000 0.000

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.356(4) . ?
N1 C2 1.370(3) . ?
N1 Li1 1.949(2) . ?
N2 C2 1.334(4) 2_655 ?
N2 C1 1.339(4) . ?
C1 C4 1.475(4) . ?
C2 N2 1.334(4) 10_566 ?
C2 C3 1.470(4) . ?
C3 C4 1.389(4) . ?
C3 C8 1.392(4) . ?
C4 C5 1.379(4) . ?
C5 C6 1.392(5) . ?
C5 H1 0.9500 . ?
C6 C7 1.381(5) . ?
C6 H2 0.9500 . ?
C7 C8 1.391(5) . ?
C7 H3 0.9500 . ?
C8 H4 0.9500 . ?
Li1 N1 1.949(2) 9_666 ?
Li1 N1 1.949(2) 10_566 ?
Li1 N1 1.949(2) 2_655 ?
Li1 Li1 3.2070(15) 5_655 ?
Li1 Li1 3.2070(15) 5_654 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 107.7(2) . . ?
C1 N1 Li1 126.31(19) . . ?
C2 N1 Li1 125.96(19) . . ?
C2 N2 C1 121.8(2) 2_655 . ?
N2 C1 N1 128.0(3) . . ?
N2 C1 C4 121.7(2) . . ?
N1 C1 C4 110.3(2) . . ?
N2 C2 N1 127.9(3) 10_566 . ?
N2 C2 C3 122.2(2) 10_566 . ?
N1 C2 C3 110.0(3) . . ?
C4 C3 C8 120.7(3) . . ?
C4 C3 C2 106.1(2) . . ?
C8 C3 C2 133.2(3) . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 C1 132.2(3) . . ?
C3 C4 C1 105.9(2) . . ?
C4 C5 C6 117.2(3) . . ?
C4 C5 H1 121.4 . . ?
C6 C5 H1 121.4 . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H2 119.2 . . ?
C5 C6 H2 119.2 . . ?
C6 C7 C8 121.1(3) . . ?
C6 C7 H3 119.4 . . ?
C8 C7 H3 119.4 . . ?
C7 C8 C3 117.6(3) . . ?
C7 C8 H4 121.2 . . ?
C3 C8 H4 121.2 . . ?
N1 Li1 N1 180.0 9_666 . ?
N1 Li1 N1 90.0 9_666 10_566 ?
N1 Li1 N1 90.0 . 10_566 ?
N1 Li1 N1 90.0 9_666 2_655 ?
N1 Li1 N1 90.0 . 2_655 ?
N1 Li1 N1 180.0 10_566 2_655 ?
N1 Li1 Li1 90.0 9_666 5_655 ?
N1 Li1 Li1 90.0 . 5_655 ?
N1 Li1 Li1 90.0 10_566 5_655 ?
N1 Li1 Li1 90.0 2_655 5_655 ?
N1 Li1 Li1 90.0 9_666 5_654 ?
N1 Li1 Li1 90.0 . 5_654 ?
N1 Li1 Li1 90.0 10_566 5_654 ?
N1 Li1 Li1 90.0 2_655 5_654 ?
Li1 Li1 Li1 180.0 5_655 5_654 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C1 N1 0.0 2_655 . . . ?
C2 N2 C1 C4 180.0 2_655 . . . ?
C2 N1 C1 N2 180.0 . . . . ?
Li1 N1 C1 N2 0.0 . . . . ?
C2 N1 C1 C4 0.0 . . . . ?
Li1 N1 C1 C4 180.0 . . . . ?
C1 N1 C2 N2 180.0 . . . 10_566 ?
Li1 N1 C2 N2 0.0 . . . 10_566 ?
C1 N1 C2 C3 0.0 . . . . ?
Li1 N1 C2 C3 180.0 . . . . ?
N2 C2 C3 C4 180.0 10_566 . . . ?
N1 C2 C3 C4 0.0 . . . . ?
N2 C2 C3 C8 0.0 10_566 . . . ?
N1 C2 C3 C8 180.0 . . . . ?
C8 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 C5 180.0 . . . . ?
C8 C3 C4 C1 180.0 . . . . ?
C2 C3 C4 C1 0.0 . . . . ?
N2 C1 C4 C5 0.0 . . . . ?
N1 C1 C4 C5 180.0 . . . . ?
N2 C1 C4 C3 180.0 . . . . ?
N1 C1 C4 C3 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C1 C4 C5 C6 180.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C6 C7 C8 C3 0.0 . . . . ?
C4 C3 C8 C7 0.0 . . . . ?
C2 C3 C8 C7 180.0 . . . . ?
C1 N1 Li1 N1 0.0 . . . 9_666 ?
C2 N1 Li1 N1 0(100) . . . 9_666 ?
C1 N1 Li1 N1 180.0 . . . 10_566 ?
C2 N1 Li1 N1 0.0 . . . 10_566 ?
C1 N1 Li1 N1 0.0 . . . 2_655 ?
C2 N1 Li1 N1 180.0 . . . 2_655 ?
C1 N1 Li1 Li1 -90.0 . . . 5_655 ?
C2 N1 Li1 Li1 90.0 . . . 5_655 ?
C1 N1 Li1 Li1 90.0 . . . 5_654 ?
C2 N1 Li1 Li1 -90.0 . . . 5_654 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 979681'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_LiPcCl024

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
lithium phthalocyanine chloride 
;
_chemical_name_common            'lithium phthalocyanine chloride'
_chemical_melting_point          400K
_chemical_formula_moiety         'C32 H16 Cl0.24 Li N8 '
_chemical_formula_sum            'C32 H16 Cl0.24 Li N8'
_chemical_formula_weight         527.63

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'
Li Li -0.0003 0.0001 '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           tetragonal
_symmetry_space_group_name_H-M   'P 4/m c c'
_symmetry_space_group_name_Hall  '-P 4 2c'
_symmetry_Int_Tables_number      124

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

_cell_length_a                   13.841(4)
_cell_length_b                   13.841(4)
_cell_length_c                   6.4027(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1226.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2664
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.4

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      1.43
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             542.16
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            9097
_diffrn_reflns_av_R_equivalents  0.051

_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         27.48
_reflns_number_total             772
_reflns_number_gt                668
_reflns_threshold_expression     >2sigma(I)


_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3

_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)+(0.0479P)²+0.5321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_number_reflns         772
_refine_ls_number_parameters     66
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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 0.0000 0.0000 0.2500 0.319(18) Uani 0.24 8 d SP . .
N1 N 0.27040(11) 0.41878(12) 0.5000 0.0243(4) Uani 1 2 d S . .
N2 N 0.43943(11) 0.37280(11) 0.5000 0.0231(4) Uani 1 2 d S . .
C3 C 0.48558(14) 0.28682(13) 0.5000 0.0229(4) Uani 1 2 d S . .
C4 C 0.34239(14) 0.35480(14) 0.5000 0.0231(4) Uani 1 2 d S . .
C5 C 0.32464(14) 0.24990(14) 0.5000 0.0250(4) Uani 1 2 d S . .
C6 C 0.41528(15) 0.20693(14) 0.5000 0.0254(5) Uani 1 2 d S . .
C7 C 0.42614(17) 0.10781(15) 0.5000 0.0339(5) Uani 1 2 d S . .
H1 H 0.4883 0.0787 0.5000 0.041 Uiso 1 2 calc SR . .
C8 C 0.24091(16) 0.19469(15) 0.5000 0.0323(5) Uani 1 2 d S . .
H2 H 0.1788 0.2239 0.5000 0.039 Uiso 1 2 calc SR . .
C9 C 0.25180(18) 0.09470(17) 0.5000 0.0393(6) Uani 1 2 d S . .
H3 H 0.1960 0.0548 0.5000 0.047 Uiso 1 2 calc SR . .
C10 C 0.34247(17) 0.05222(16) 0.5000 0.0405(6) Uani 1 2 d S . .
H4 H 0.3476 -0.0162 0.5000 0.049 Uiso 1 2 calc SR . .
Li11 Li 0.5000 0.5000 0.5000 0.0327(16) Uani 1 8 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 0.111(5) 0.111(5) 0.73(6) 0.000 0.000 0.000
N1 0.0214(8) 0.0234(8) 0.0281(9) 0.000 0.000 -0.0008(6)
N2 0.0196(8) 0.0222(8) 0.0274(9) 0.000 0.000 -0.0002(6)
C3 0.0269(10) 0.0192(9) 0.0228(9) 0.000 0.000 -0.0007(7)
C4 0.0239(10) 0.0224(10) 0.0231(10) 0.000 0.000 -0.0024(7)
C5 0.0272(10) 0.0228(10) 0.0248(9) 0.000 0.000 -0.0034(8)
C6 0.0297(11) 0.0208(10) 0.0256(10) 0.000 0.000 -0.0029(8)
C7 0.0372(12) 0.0202(10) 0.0442(13) 0.000 0.000 -0.0015(8)
C8 0.0307(11) 0.0311(12) 0.0351(11) 0.000 0.000 -0.0076(8)
C9 0.0390(13) 0.0310(12) 0.0479(15) 0.000 0.000 -0.0154(10)
C10 0.0480(14) 0.0202(10) 0.0534(15) 0.000 0.000 -0.0081(9)
Li11 0.026(2) 0.026(2) 0.046(4) 0.000 0.000 0.000

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.333(3) . ?
N1 C3 1.343(3) 10_566 ?
N2 C3 1.351(2) . ?
N2 C4 1.366(2) . ?
N2 Li11 1.9500(17) . ?
C3 N1 1.343(3) 2_655 ?
C3 C6 1.473(3) . ?
C4 C5 1.473(3) . ?
C5 C8 1.388(3) . ?
C5 C6 1.388(3) . ?
C6 C7 1.380(3) . ?
C7 C10 1.390(3) . ?
C7 H1 0.9500 . ?
C8 C9 1.392(3) . ?
C8 H2 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H3 0.9500 . ?
C10 H4 0.9500 . ?
Li11 N2 1.9500(17) 9_666 ?
Li11 N2 1.9500(17) 10_566 ?
Li11 N2 1.9500(17) 2_655 ?
Li11 Li11 3.2013(9) 5_655 ?
Li11 Li11 3.2013(9) 5_654 ?

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
C4 N1 C3 121.88(16) . 10_566 ?
C3 N2 C4 107.72(16) . . ?
C3 N2 Li11 126.31(13) . . ?
C4 N2 Li11 125.97(13) . . ?
N1 C3 N2 127.97(17) 2_655 . ?
N1 C3 C6 121.60(17) 2_655 . ?
N2 C3 C6 110.43(17) . . ?
N1 C4 N2 127.86(17) . . ?
N1 C4 C5 122.02(17) . . ?
N2 C4 C5 110.11(17) . . ?
C8 C5 C6 121.23(18) . . ?
C8 C5 C4 133.00(19) . . ?
C6 C5 C4 105.76(16) . . ?
C7 C6 C5 121.61(19) . . ?
C7 C6 C3 132.4(2) . . ?
C5 C6 C3 105.98(17) . . ?
C6 C7 C10 117.3(2) . . ?
C6 C7 H1 121.3 . . ?
C10 C7 H1 121.3 . . ?
C5 C8 C9 117.2(2) . . ?
C5 C8 H2 121.4 . . ?
C9 C8 H2 121.4 . . ?
C10 C9 C8 121.3(2) . . ?
C10 C9 H3 119.3 . . ?
C8 C9 H3 119.3 . . ?
C9 C10 C7 121.3(2) . . ?
C9 C10 H4 119.4 . . ?
C7 C10 H4 119.4 . . ?
N2 Li11 N2 180.0 9_666 . ?
N2 Li11 N2 90.0 9_666 10_566 ?
N2 Li11 N2 90.0 . 10_566 ?
N2 Li11 N2 90.0 9_666 2_655 ?
N2 Li11 N2 90.0 . 2_655 ?
N2 Li11 N2 180.0 10_566 2_655 ?
N2 Li11 Li11 90.0 9_666 5_655 ?
N2 Li11 Li11 90.0 . 5_655 ?
N2 Li11 Li11 90.0 10_566 5_655 ?
N2 Li11 Li11 90.0 2_655 5_655 ?
N2 Li11 Li11 90.0 9_666 5_654 ?
N2 Li11 Li11 90.0 . 5_654 ?
N2 Li11 Li11 90.0 10_566 5_654 ?
N2 Li11 Li11 90.0 2_655 5_654 ?
Li11 Li11 Li11 180.0 5_655 5_654 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N2 C3 N1 180.0 . . . 2_655 ?
Li11 N2 C3 N1 0.0 . . . 2_655 ?
C4 N2 C3 C6 0.0 . . . . ?
Li11 N2 C3 C6 180.0 . . . . ?
C3 N1 C4 N2 0.0 10_566 . . . ?
C3 N1 C4 C5 180.0 10_566 . . . ?
C3 N2 C4 N1 180.0 . . . . ?
Li11 N2 C4 N1 0.0 . . . . ?
C3 N2 C4 C5 0.0 . . . . ?
Li11 N2 C4 C5 180.0 . . . . ?
N1 C4 C5 C8 0.0 . . . . ?
N2 C4 C5 C8 180.0 . . . . ?
N1 C4 C5 C6 180.0 . . . . ?
N2 C4 C5 C6 0.0 . . . . ?
C8 C5 C6 C7 0.0 . . . . ?
C4 C5 C6 C7 180.0 . . . . ?
C8 C5 C6 C3 180.0 . . . . ?
C4 C5 C6 C3 0.0 . . . . ?
N1 C3 C6 C7 0.0 2_655 . . . ?
N2 C3 C6 C7 180.0 . . . . ?
N1 C3 C6 C5 180.0 2_655 . . . ?
N2 C3 C6 C5 0.0 . . . . ?
C5 C6 C7 C10 0.0 . . . . ?
C3 C6 C7 C10 180.0 . . . . ?
C6 C5 C8 C9 0.0 . . . . ?
C4 C5 C8 C9 180.0 . . . . ?
C5 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C7 0.0 . . . . ?
C6 C7 C10 C9 0.0 . . . . ?
C3 N2 Li11 N2 0.0 . . . 9_666 ?
C4 N2 Li11 N2 180.0 . . . 9_666 ?
C3 N2 Li11 N2 180.0 . . . 10_566 ?
C4 N2 Li11 N2 0.0 . . . 10_566 ?
C3 N2 Li11 N2 0.0 . . . 2_655 ?
C4 N2 Li11 N2 180.0 . . . 2_655 ?
C3 N2 Li11 Li11 -90.0 . . . 5_655 ?
C4 N2 Li11 Li11 90.0 . . . 5_655 ?
C3 N2 Li11 Li11 90.0 . . . 5_654 ?
C4 N2 Li11 Li11 -90.0 . . . 5_654 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 979682'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_LiPcCl038

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
lithium phthalocyanine chloride 
;
_chemical_name_common            'lithium phthalocyanine chloride'
_chemical_melting_point          400K
_chemical_formula_moiety         'C32 H16 Li Cl0.38 N8'
_chemical_formula_sum            'C32 H16 Cl0.38 Li N8'
_chemical_formula_weight         533.30

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'
Li Li -0.0003 0.0001 '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           tetragonal
_symmetry_space_group_name_H-M   'P 4/m c c'
_symmetry_space_group_name_Hall  '-P 4 2c'
_symmetry_Int_Tables_number      124

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

_cell_length_a                   13.843(4)
_cell_length_b                   13.843(4)
_cell_length_c                   6.394(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1225.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2719
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      1.47
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             546.9
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            8965
_diffrn_reflns_av_R_equivalents  0.109
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         27.44
_reflns_number_total             768
_reflns_number_gt                664
_reflns_threshold_expression     >2sigma(I)

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3

_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)+(0.0788P)²+0.6382P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         768
_refine_ls_number_parameters     66
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1611
_refine_ls_wR_factor_gt          0.1542
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_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 0.0000 1.0000 0.2500 0.252(9) Uani 0.38 8 d SP . .
N1 N 0.27035(14) 0.41858(15) 0.5000 0.0237(5) Uani 1 2 d S . .
N2 N 0.37294(14) 0.56053(13) 0.5000 0.0223(5) Uani 1 2 d S . .
C1 C 0.34224(17) 0.35476(17) 0.5000 0.0229(6) Uani 1 2 d S . .
C4 C 0.24967(16) 0.67527(17) 0.5000 0.0242(6) Uani 1 2 d S . .
C5 C 0.28692(15) 0.51430(17) 0.5000 0.0222(6) Uani 1 2 d S . .
C6 C 0.20677(17) 0.58435(17) 0.5000 0.0243(6) Uani 1 2 d S . .
C7 C 0.19473(18) 0.75866(19) 0.5000 0.0308(6) Uani 1 2 d S . .
H1 H 0.2240 0.8207 0.5000 0.037 Uiso 1 2 calc SR . .
C8 C 0.05189(19) 0.6572(2) 0.5000 0.0379(7) Uani 1 2 d S . .
H2 H -0.0165 0.6520 0.5000 0.046 Uiso 1 2 calc SR . .
C9 C 0.0944(2) 0.7479(2) 0.5000 0.0374(7) Uani 1 2 d S . .
H3 H 0.0546 0.8037 0.5000 0.045 Uiso 1 2 calc SR . .
C10 C 0.10782(18) 0.5737(2) 0.5000 0.0319(7) Uani 1 2 d S . .
H4 H 0.0788 0.5116 0.5000 0.038 Uiso 1 2 calc SR . .
Li12 Li 0.5000 0.5000 0.5000 0.0320(19) Uani 1 8 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 0.0485(18) 0.0485(18) 0.66(3) 0.000 0.000 0.000
N1 0.0203(10) 0.0219(10) 0.0289(11) 0.000 0.000 -0.0006(8)
N2 0.0221(10) 0.0175(10) 0.0273(10) 0.000 0.000 -0.0001(7)
C1 0.0231(12) 0.0216(12) 0.0239(11) 0.000 0.000 -0.0016(8)
C4 0.0206(12) 0.0265(12) 0.0254(11) 0.000 0.000 0.0030(9)
C5 0.0191(11) 0.0238(12) 0.0236(11) 0.000 0.000 0.0011(9)
C6 0.0206(12) 0.0268(12) 0.0256(12) 0.000 0.000 0.0023(9)
C7 0.0291(14) 0.0292(13) 0.0342(13) 0.000 0.000 0.0050(10)
C8 0.0209(13) 0.0418(16) 0.0511(18) 0.000 0.000 0.0071(11)
C9 0.0296(14) 0.0336(14) 0.0489(18) 0.000 0.000 0.0136(11)
C10 0.0216(13) 0.0332(14) 0.0409(15) 0.000 0.000 0.0020(10)
Li12 0.021(2) 0.021(2) 0.054(5) 0.000 0.000 0.000

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.331(3) . ?
N1 C5 1.345(3) . ?
N2 C5 1.352(3) . ?
N2 C1 1.369(3) 10_566 ?
N2 Li12 1.948(2) . ?
C1 N2 1.369(3) 2_655 ?
C1 C4 1.475(3) 2_655 ?
C4 C7 1.382(3) . ?
C4 C6 1.392(3) . ?
C4 C1 1.475(3) 10_566 ?
C5 C6 1.474(3) . ?
C6 C10 1.378(3) . ?
C7 C9 1.396(4) . ?
C7 H1 0.9500 . ?
C8 C9 1.387(4) . ?
C8 C10 1.391(4) . ?
C8 H2 0.9500 . ?
C9 H3 0.9500 . ?
C10 H4 0.9500 . ?
Li12 N2 1.948(2) 10_566 ?
Li12 N2 1.948(2) 2_655 ?
Li12 N2 1.948(2) 9_666 ?
Li12 Li12 3.1970(10) 5_655 ?
Li12 Li12 3.1970(10) 5_654 ?

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 C5 121.78(19) . . ?
C5 N2 C1 107.66(19) . 10_566 ?
C5 N2 Li12 126.28(15) . . ?
C1 N2 Li12 126.07(16) 10_566 . ?
N1 C1 N2 127.8(2) . 2_655 ?
N1 C1 C4 122.1(2) . 2_655 ?
N2 C1 C4 110.1(2) 2_655 2_655 ?
C7 C4 C6 121.4(2) . . ?
C7 C4 C1 132.8(2) . 10_566 ?
C6 C4 C1 105.8(2) . 10_566 ?
N1 C5 N2 128.1(2) . . ?
N1 C5 C6 121.3(2) . . ?
N2 C5 C6 110.59(19) . . ?
C10 C6 C4 121.4(2) . . ?
C10 C6 C5 132.7(2) . . ?
C4 C6 C5 105.90(19) . . ?
C4 C7 C9 117.2(2) . . ?
C4 C7 H1 121.4 . . ?
C9 C7 H1 121.4 . . ?
C9 C8 C10 121.0(3) . . ?
C9 C8 H2 119.5 . . ?
C10 C8 H2 119.5 . . ?
C8 C9 C7 121.3(3) . . ?
C8 C9 H3 119.4 . . ?
C7 C9 H3 119.4 . . ?
C6 C10 C8 117.7(3) . . ?
C6 C10 H4 121.1 . . ?
C8 C10 H4 121.1 . . ?
N2 Li12 N2 180.0 10_566 2_655 ?
N2 Li12 N2 90.0 10_566 9_666 ?
N2 Li12 N2 90.0 2_655 9_666 ?
N2 Li12 N2 90.0 10_566 . ?
N2 Li12 N2 90.0 2_655 . ?
N2 Li12 N2 180.0 9_666 . ?
N2 Li12 Li12 90.0 10_566 5_655 ?
N2 Li12 Li12 90.0 2_655 5_655 ?
N2 Li12 Li12 90.0 9_666 5_655 ?
N2 Li12 Li12 90.0 . 5_655 ?
N2 Li12 Li12 90.0 10_566 5_654 ?
N2 Li12 Li12 90.0 2_655 5_654 ?
N2 Li12 Li12 90.0 9_666 5_654 ?
N2 Li12 Li12 90.0 . 5_654 ?
Li12 Li12 Li12 180.0 5_655 5_654 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 N2 0.0 . . . 2_655 ?
C5 N1 C1 C4 180.0 . . . 2_655 ?
C1 N1 C5 N2 0.0 . . . . ?
C1 N1 C5 C6 180.0 . . . . ?
C1 N2 C5 N1 180.0 10_566 . . . ?
Li12 N2 C5 N1 0.0 . . . . ?
C1 N2 C5 C6 0.0 10_566 . . . ?
Li12 N2 C5 C6 180.0 . . . . ?
C7 C4 C6 C10 0.0 . . . . ?
C1 C4 C6 C10 180.0 10_566 . . . ?
C7 C4 C6 C5 180.0 . . . . ?
C1 C4 C6 C5 0.0 10_566 . . . ?
N1 C5 C6 C10 0.0 . . . . ?
N2 C5 C6 C10 180.0 . . . . ?
N1 C5 C6 C4 180.0 . . . . ?
N2 C5 C6 C4 0.0 . . . . ?
C6 C4 C7 C9 0.0 . . . . ?
C1 C4 C7 C9 180.0 10_566 . . . ?
C10 C8 C9 C7 0.0 . . . . ?
C4 C7 C9 C8 0.0 . . . . ?
C4 C6 C10 C8 0.0 . . . . ?
C5 C6 C10 C8 180.0 . . . . ?
C9 C8 C10 C6 0.0 . . . . ?
C5 N2 Li12 N2 180.0 . . . 10_566 ?
C1 N2 Li12 N2 0.0 10_566 . . 10_566 ?
C5 N2 Li12 N2 0.0 . . . 2_655 ?
C1 N2 Li12 N2 180.0 10_566 . . 2_655 ?
C5 N2 Li12 N2 0.0 . . . 9_666 ?
C1 N2 Li12 N2 180.0 10_566 . . 9_666 ?
C5 N2 Li12 Li12 -90.0 . . . 5_655 ?
C1 N2 Li12 Li12 90.0 10_566 . . 5_655 ?
C5 N2 Li12 Li12 90.0 . . . 5_654 ?
C1 N2 Li12 Li12 -90.0 10_566 . . 5_654 ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.898
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 979683'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_LiPcCl046

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
lithium phthalocyanine chloride
;
_chemical_name_common            'lithium phthalocyanine chloride'
_chemical_melting_point          400K
_chemical_formula_moiety         'C32 H16 Li N8, 0.46(Cl)'
_chemical_formula_sum            'C32 H16 Cl0.46 Li N8'
_chemical_formula_weight         535.78
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'
Li Li -0.0003 0.0001 '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           tetragonal
_symmetry_space_group_name_H-M   'P 4/m c c'
_symmetry_space_group_name_Hall  '-P 4 2c'
_symmetry_Int_Tables_number      124

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

_cell_length_a                   13.8605(7)
_cell_length_b                   13.8605(7)
_cell_length_c                   6.3917(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1227.93(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2810
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             549.6
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9615
_exptl_absorpt_correction_T_max  0.9615
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9039
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         27.47
_reflns_number_total             774
_reflns_number_gt                670
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0743P)²+0.6202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         774
_refine_ls_number_parameters     66
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.1419
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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 1.0000 1.0000 0.7500 0.223(6) Uani 0.46 8 d SP . .
N1 N 0.56026(12) 0.62685(13) 0.5000 0.0220(5) Uani 1 2 d S . .
N2 N 0.72937(13) 0.58132(14) 0.5000 0.0229(5) Uani 1 2 d S . .
C3 C 0.67487(16) 0.75001(15) 0.5000 0.0233(5) Uani 1 2 d S . .
C4 C 0.58414(17) 0.79296(16) 0.5000 0.0236(5) Uani 1 2 d S . .
C5 C 0.65738(16) 0.64524(16) 0.5000 0.0221(5) Uani 1 2 d S . .
C6 C 0.51405(16) 0.71285(15) 0.5000 0.0216(5) Uani 1 2 d S . .
C7 C 0.6568(2) 0.94769(18) 0.5000 0.0377(7) Uani 1 2 d S . .
H1 H 0.6516 1.0160 0.5000 0.045 Uiso 1 2 calc SR . .
C8 C 0.57312(19) 0.89180(17) 0.5000 0.0313(6) Uani 1 2 d S . .
H2 H 0.5110 0.9207 0.5000 0.038 Uiso 1 2 calc SR . .
C9 C 0.7474(2) 0.90529(19) 0.5000 0.0370(7) Uani 1 2 d S . .
H3 H 0.8031 0.9451 0.5000 0.044 Uiso 1 2 calc SR . .
C10 C 0.75826(18) 0.80504(17) 0.5000 0.0300(6) Uani 1 2 d S . .
H4 H 0.8203 0.7759 0.5000 0.036 Uiso 1 2 calc SR . .
Li11 Li 0.5000 0.5000 0.5000 0.0292(17) Uani 1 8 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 0.0575(17) 0.0575(17) 0.553(19) 0.000 0.000 0.000
N1 0.0191(9) 0.0219(9) 0.0249(10) 0.000 0.000 0.0004(7)
N2 0.0194(9) 0.0229(10) 0.0263(10) 0.000 0.000 -0.0001(7)
C3 0.0253(11) 0.0221(11) 0.0225(10) 0.000 0.000 -0.0027(9)
C4 0.0263(11) 0.0210(11) 0.0237(11) 0.000 0.000 -0.0036(9)
C5 0.0228(11) 0.0215(11) 0.0220(11) 0.000 0.000 -0.0017(8)
C6 0.0238(11) 0.0181(10) 0.0229(11) 0.000 0.000 -0.0004(8)
C7 0.0410(15) 0.0208(12) 0.0514(17) 0.000 0.000 -0.0066(10)
C8 0.0320(13) 0.0210(11) 0.0409(14) 0.000 0.000 -0.0015(9)
C9 0.0341(14) 0.0276(13) 0.0493(17) 0.000 0.000 -0.0122(11)
C10 0.0271(12) 0.0289(13) 0.0340(13) 0.000 0.000 -0.0050(9)
Li11 0.020(2) 0.020(2) 0.048(5) 0.000 0.000 0.000

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.353(3) . ?
N1 C5 1.370(3) . ?
N1 Li11 1.9464(18) . ?
N2 C5 1.334(3) . ?
N2 C6 1.342(3) 10_566 ?
C3 C10 1.385(3) . ?
C3 C4 1.391(3) . ?
C3 C5 1.472(3) . ?
C4 C8 1.378(3) . ?
C4 C6 1.475(3) . ?
C6 N2 1.342(3) 2_655 ?
C7 C9 1.386(4) . ?
C7 C8 1.395(4) . ?
C7 H1 0.9500 . ?
C8 H2 0.9500 . ?
C9 C10 1.398(3) . ?
C9 H3 0.9500 . ?
C10 H4 0.9500 . ?
Li11 N1 1.9464(18) 9_666 ?
Li11 N1 1.9464(18) 10_566 ?
Li11 N1 1.9464(18) 2_655 ?
Li11 Li11 3.1958(3) 5_655 ?
Li11 Li11 3.1958(3) 5_654 ?

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
C6 N1 C5 107.53(18) . . ?
C6 N1 Li11 126.34(15) . . ?
C5 N1 Li11 126.13(15) . . ?
C5 N2 C6 121.78(18) . 10_566 ?
C10 C3 C4 121.2(2) . . ?
C10 C3 C5 132.9(2) . . ?
C4 C3 C5 105.86(19) . . ?
C8 C4 C3 121.7(2) . . ?
C8 C4 C6 132.5(2) . . ?
C3 C4 C6 105.85(18) . . ?
N2 C5 N1 127.7(2) . . ?
N2 C5 C3 122.13(19) . . ?
N1 C5 C3 110.2(2) . . ?
N2 C6 N1 128.1(2) 2_655 . ?
N2 C6 C4 121.36(19) 2_655 . ?
N1 C6 C4 110.56(18) . . ?
C9 C7 C8 121.2(2) . . ?
C9 C7 H1 119.4 . . ?
C8 C7 H1 119.4 . . ?
C4 C8 C7 117.4(2) . . ?
C4 C8 H2 121.3 . . ?
C7 C8 H2 121.3 . . ?
C7 C9 C10 121.3(2) . . ?
C7 C9 H3 119.4 . . ?
C10 C9 H3 119.4 . . ?
C3 C10 C9 117.2(2) . . ?
C3 C10 H4 121.4 . . ?
C9 C10 H4 121.4 . . ?
N1 Li11 N1 180.000(1) . 9_666 ?
N1 Li11 N1 90.0 . 10_566 ?
N1 Li11 N1 90.0 9_666 10_566 ?
N1 Li11 N1 90.0 . 2_655 ?
N1 Li11 N1 90.0 9_666 2_655 ?
N1 Li11 N1 180.0 10_566 2_655 ?
N1 Li11 Li11 90.0 . 5_655 ?
N1 Li11 Li11 90.0 9_666 5_655 ?
N1 Li11 Li11 90.0 10_566 5_655 ?
N1 Li11 Li11 90.0 2_655 5_655 ?
N1 Li11 Li11 90.0 . 5_654 ?
N1 Li11 Li11 90.0 9_666 5_654 ?
N1 Li11 Li11 90.0 10_566 5_654 ?
N1 Li11 Li11 90.0 2_655 5_654 ?
Li11 Li11 Li11 180.0 5_655 5_654 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C3 C4 C8 0.0 . . . . ?
C5 C3 C4 C8 180.0 . . . . ?
C10 C3 C4 C6 180.0 . . . . ?
C5 C3 C4 C6 0.0 . . . . ?
C6 N2 C5 N1 0.0 10_566 . . . ?
C6 N2 C5 C3 180.0 10_566 . . . ?
C6 N1 C5 N2 180.0 . . . . ?
Li11 N1 C5 N2 0.0 . . . . ?
C6 N1 C5 C3 0.0 . . . . ?
Li11 N1 C5 C3 180.0 . . . . ?
C10 C3 C5 N2 0.0 . . . . ?
C4 C3 C5 N2 180.0 . . . . ?
C10 C3 C5 N1 180.0 . . . . ?
C4 C3 C5 N1 0.0 . . . . ?
C5 N1 C6 N2 180.0 . . . 2_655 ?
Li11 N1 C6 N2 0.0 . . . 2_655 ?
C5 N1 C6 C4 0.0 . . . . ?
Li11 N1 C6 C4 180.0 . . . . ?
C8 C4 C6 N2 0.0 . . . 2_655 ?
C3 C4 C6 N2 180.0 . . . 2_655 ?
C8 C4 C6 N1 180.0 . . . . ?
C3 C4 C6 N1 0.0 . . . . ?
C3 C4 C8 C7 0.0 . . . . ?
C6 C4 C8 C7 180.0 . . . . ?
C9 C7 C8 C4 0.0 . . . . ?
C8 C7 C9 C10 0.0 . . . . ?
C4 C3 C10 C9 0.0 . . . . ?
C5 C3 C10 C9 180.0 . . . . ?
C7 C9 C10 C3 0.0 . . . . ?
C6 N1 Li11 N1 0.0 . . . 9_666 ?
C5 N1 Li11 N1 180.0 . . . 9_666 ?
C6 N1 Li11 N1 180.0 . . . 10_566 ?
C5 N1 Li11 N1 0.0 . . . 10_566 ?
C6 N1 Li11 N1 0.0 . . . 2_655 ?
C5 N1 Li11 N1 180.0 . . . 2_655 ?
C6 N1 Li11 Li11 -90.0 . . . 5_655 ?
C5 N1 Li11 Li11 90.0 . . . 5_655 ?
C6 N1 Li11 Li11 90.0 . . . 5_654 ?
C5 N1 Li11 Li11 -90.0 . . . 5_654 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.962
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 996929'
