#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/32/2013291.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2013291
loop_
_publ_author_name
'Jan Janczak'
'Ryszard Kubiak'
_publ_section_title
;
 Two isomorphous complexes: dichloro[phthalocyaninato(2--)]tin(IV) and
 dichloro[phthalocyaninato(2--)]germanium(IV)
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m237
_journal_page_last               m240
_journal_paper_doi               10.1107/S0108270103009417
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '[Ge (C32 H16 N8) Cl2]'
_chemical_formula_moiety         'C32 H16 Cl2 Ge N8'
_chemical_formula_sum            'C32 H16 Cl2 Ge N8'
_chemical_formula_weight         656.02
_chemical_melting_point          sublimation
_chemical_name_common            'dichlorphthalocyanine germanium'
_chemical_name_systematic
;
 dichloro(phthalocyaninato(2-))germanium(IV)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                73.85(3)
_cell_angle_beta                 80.61(3)
_cell_angle_gamma                86.39(3)
_cell_formula_units_Z            1
_cell_length_a                   7.3650(10)
_cell_length_b                   8.704(2)
_cell_length_c                   10.966(2)
_cell_measurement_reflns_used    3082
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2.8
_cell_volume                     666.1(2)
_computing_cell_refinement       'KM-4 CCD software'
_computing_data_collection       'KM-4 CCD software (Kuma, 2000)'
_computing_data_reduction        'KM-4 CCD software'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'KUMA KM-4 CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5657
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    1.392
_exptl_absorpt_correction_T_max  0.787
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
face-indexed, SHELXTL (Sheldrick, 1990)
;
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_meas      1.63
_exptl_crystal_density_method    floatation
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.285
_refine_ls_extinction_coef       0.110(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0686P)²+0.2297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1511
_reflns_number_gt                1936
_reflns_number_total             3082
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1161.cif
_cod_data_source_block           IIa
_cod_database_code               2013291
_cod_database_fobs_code          2013291
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Ge 0.5000 0.0000 0.5000 0.0816(3) Uani d S 1 . . Ge
Cl 0.22982(11) 0.14435(10) 0.41116(8) 0.0687(3) Uani d . 1 . . Cl
N1 0.3866(5) -0.3169(4) 0.4072(3) 0.0841(9) Uani d . 1 . . N
N2 0.5651(4) -0.0748(4) 0.3434(3) 0.0763(8) Uani d . 1 . . N
N3 0.7611(4) 0.1418(4) 0.2114(3) 0.0796(9) Uani d . 1 . . N
N4 0.6527(5) 0.1896(4) 0.4186(3) 0.0851(9) Uani d . 1 . . N
C1 0.4963(5) -0.2066(4) 0.3231(4) 0.0766(10) Uani d . 1 . . C
C2 0.5612(5) -0.2122(5) 0.1943(4) 0.0825(10) Uani d . 1 . . C
C3 0.5343(6) -0.3205(5) 0.1253(4) 0.0883(11) Uani d . 1 . . C
H3 0.4639 -0.4112 0.1641 0.106 Uiso calc R 1 . . H
C4 0.6131(7) -0.2898(6) 0.0008(5) 0.1025(14) Uani d . 1 . . C
H4 0.5947 -0.3589 -0.0470 0.123 Uiso calc R 1 . . H
C5 0.7237(6) -0.1532(5) -0.0578(4) 0.0918(12) Uani d . 1 . . C
H5 0.7770 -0.1334 -0.1434 0.110 Uiso calc R 1 . . H
C6 0.7514(6) -0.0521(5) 0.0105(4) 0.0840(11) Uani d . 1 . . C
H6 0.8263 0.0359 -0.0272 0.101 Uiso calc R 1 . . H
C7 0.6693(6) -0.0794(5) 0.1350(4) 0.0814(10) Uani d . 1 . . C
C8 0.6717(5) 0.0053(4) 0.2335(4) 0.0759(9) Uani d . 1 . . C
C9 0.7496(5) 0.2191(4) 0.2967(4) 0.0759(9) Uani d . 1 . . C
C10 0.8628(7) 0.3607(6) 0.2798(4) 0.1078(18) Uani d . 1 . . C
C11 0.9684(6) 0.4542(5) 0.1683(5) 0.0928(13) Uani d . 1 . . C
H11 0.9943 0.4233 0.0926 0.111 Uiso calc R 1 . . H
C12 1.0318(6) 0.5973(5) 0.1796(5) 0.0923(12) Uani d . 1 . . C
H12 1.1077 0.6610 0.1102 0.111 Uiso calc R 1 . . H
C13 0.9866(6) 0.6470(5) 0.2889(5) 0.0979(14) Uani d . 1 . . C
H13 1.0386 0.7394 0.2936 0.117 Uiso calc R 1 . . H
C14 0.8694(6) 0.5657(5) 0.3890(5) 0.0850(11) Uani d . 1 . . C
H14 0.8354 0.6043 0.4606 0.102 Uiso calc R 1 . . H
C15 0.7998(5) 0.4252(5) 0.3854(4) 0.0799(10) Uani d . 1 . . C
C16 0.6775(5) 0.3097(4) 0.4740(4) 0.0777(10) Uani d . 1 . . C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 Ge Cl . . 89.09(10) y
N4 Ge Cl . . 90.71(11) y
N4 Ge N2 2_656 . 89.83(13) y
N2 Ge N4 . . 90.17(13) y
N4 Ge N4 2_656 . 180.00(13) ?
N4 Ge N2 2_656 2_656 90.17(13) ?
N4 Ge N2 . 2_656 89.83(13) ?
N2 Ge N2 . 2_656 180.0 ?
N4 Ge Cl 2_656 . 89.29(11) ?
N2 Ge Cl 2_656 . 90.91(10) ?
N4 Ge Cl 2_656 2_656 90.71(11) ?
N4 Ge Cl . 2_656 89.29(11) ?
N2 Ge Cl . 2_656 90.91(10) ?
N2 Ge Cl 2_656 2_656 89.09(10) ?
Cl Ge Cl . 2_656 180.00(4) ?
C16 N1 C1 2_656 . 123.2(3) ?
C8 N2 C1 . . 108.7(3) ?
C8 N2 Ge . . 125.2(3) ?
C1 N2 Ge . . 125.8(3) ?
C9 N3 C8 . . 121.8(3) ?
C9 N4 C16 . . 110.9(3) ?
C9 N4 Ge . . 123.3(3) ?
C16 N4 Ge . . 125.7(3) ?
N1 C1 N2 . . 127.4(3) ?
N1 C1 C2 . . 123.2(4) ?
N2 C1 C2 . . 109.4(3) ?
C7 C2 C3 . . 119.8(4) ?
C7 C2 C1 . . 107.5(4) ?
C3 C2 C1 . . 132.7(4) ?
C4 C3 C2 . . 118.4(4) ?
C4 C3 H3 . . 120.8 ?
C2 C3 H3 . . 120.8 ?
C3 C4 C5 . . 120.8(4) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C6 C5 C4 . . 120.1(4) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C7 . . 119.7(4) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C6 C7 C2 . . 121.2(4) ?
C6 C7 C8 . . 133.0(4) ?
C2 C7 C8 . . 105.8(3) ?
N3 C8 N2 . . 128.0(4) ?
N3 C8 C7 . . 123.3(3) ?
N2 C8 C7 . . 108.7(3) ?
N3 C9 N4 . . 131.4(3) ?
N3 C9 C10 . . 122.7(3) ?
N4 C9 C10 . . 105.7(3) ?
C11 C10 C15 . . 120.2(4) ?
C11 C10 C9 . . 129.6(4) ?
C15 C10 C9 . . 107.2(3) ?
C12 C11 C10 . . 115.2(5) ?
C12 C11 H11 . . 122.4 ?
C10 C11 H11 . . 122.4 ?
C13 C12 C11 . . 122.6(4) ?
C13 C12 H12 . . 118.7 ?
C11 C12 H12 . . 118.7 ?
C14 C13 C12 . . 121.5(4) ?
C14 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
C13 C14 C15 . . 119.6(5) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C14 C15 C10 . . 119.9(4) ?
C14 C15 C16 . . 134.0(4) ?
C10 C15 C16 . . 106.0(3) ?
N1 C16 N4 2_656 . 127.6(3) ?
N1 C16 C15 2_656 . 123.2(4) ?
N4 C16 C15 . . 109.0(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ge Cl . 2.4747(11) y
Ge N2 . 1.979(3) y
Ge N4 . 1.968(3) y
Ge N2 2_656 1.979(3) ?
Ge Cl 2_656 2.4747(11) ?
Ge N4 2_656 1.968(3) ?
N1 C16 2_656 1.329(5) ?
N1 C1 . 1.337(5) ?
N2 C8 . 1.360(5) ?
N2 C1 . 1.369(5) ?
N3 C9 . 1.286(5) ?
N3 C8 . 1.337(5) ?
N4 C9 . 1.373(5) ?
N4 C16 . 1.381(5) ?
C1 C2 . 1.428(6) ?
C2 C7 . 1.387(6) ?
C2 C3 . 1.404(6) ?
C3 C4 . 1.353(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.420(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.347(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.361(6) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.470(6) ?
C9 C10 . 1.484(5) ?
C10 C11 . 1.406(5) ?
C10 C15 . 1.423(6) ?
C11 C12 . 1.401(6) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.369(7) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.337(6) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.368(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.432(5) ?
C16 N1 2_656 1.329(5) ?
