#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:27:25 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179378 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/75/4327507.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4327507
loop_
_publ_author_name
'Anna S. Gardberg'
'Syaulan Yang'
'Brian M. Hoffman'
'James A. Ibers'
_publ_section_title
;
 Synthesis and Structural Characterization of Integrally Oxidized,
 Metal-Free Phthalocyanine Compounds: [H2(pc)][IBr2] and
 [H2(pc)]2[IBr2]Br.C10H7Br
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1778
_journal_page_last               1781
_journal_paper_doi               10.1021/ic010994+
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C74 H43 Br4 I N16'
_chemical_formula_weight         1602.78
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           2
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.8540(10)
_cell_angle_beta                 103.4170(10)
_cell_angle_gamma                97.0490(10)
_cell_formula_units_Z            1
_cell_length_a                   8.4724(6)
_cell_length_b                   13.5794(10)
_cell_length_c                   13.8403(10)
_cell_measurement_temperature    153(2)
_cell_volume                     1535.61(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.891
_diffrn_measured_fraction_theta_max 0.891
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18538
_diffrn_reflns_theta_full        28.94
_diffrn_reflns_theta_max         28.94
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    3.186
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_F_000             792
_refine_diff_density_max         1.695
_refine_diff_density_min         -1.344
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         7249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+2.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                6213
_reflns_number_total             7249
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0109942B_2.cif
_cod_data_source_block           H2pcIBr2Br
_cod_database_code               4327507
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
I1 I 0.5000 0.5000 0.0000 0.02972(9) Uani 1 2 d S . .
Br1 Br 0.21438(4) 0.48975(3) 0.05643(3) 0.03645(10) Uani 1 1 d . . .
Br2 Br 0.0000 0.0000 0.0000 0.03999(14) Uani 1 2 d S . .
N1 N 0.6829(3) 1.04626(18) 0.40506(18) 0.0225(5) Uani 1 1 d . . .
H1A H 0.7329 1.0094 0.4513 0.027 Uiso 0.50 1 calc PR . .
N2 N 0.5805(3) 1.15919(18) 0.50580(18) 0.0219(5) Uani 1 1 d . . .
N3 N 0.7269(3) 1.04403(18) 0.61484(18) 0.0211(5) Uani 1 1 d . . .
H3B H 0.7563 1.0070 0.5710 0.025 Uiso 0.50 1 calc PR . .
N4 N 0.8488(3) 0.96190(18) 0.75949(18) 0.0214(5) Uani 1 1 d . . .
N5 N 0.9019(3) 0.88540(18) 0.61615(18) 0.0216(5) Uani 1 1 d . . .
H5B H 0.8544 0.9247 0.5716 0.026 Uiso 0.50 1 calc PR . .
N6 N 1.0013(3) 0.77169(18) 0.51262(19) 0.0238(5) Uani 1 1 d . . .
N7 N 0.8572(3) 0.88812(18) 0.40629(19) 0.0232(5) Uani 1 1 d . . .
H7A H 0.8320 0.9253 0.4517 0.028 Uiso 0.50 1 calc PR . .
N8 N 0.7337(3) 0.96939(19) 0.25809(19) 0.0239(5) Uani 1 1 d . . .
C1 C 0.6722(4) 1.0358(2) 0.3052(2) 0.0228(6) Uani 1 1 d . . .
C2 C 0.5778(4) 1.1101(2) 0.2526(2) 0.0246(6) Uani 1 1 d . . .
C3 C 0.5303(4) 1.1299(2) 0.1522(2) 0.0303(7) Uani 1 1 d . . .
H3A H 0.5585 1.0914 0.1023 0.036 Uiso 1 1 calc R . .
C4 C 0.4396(4) 1.2088(3) 0.1284(3) 0.0333(7) Uani 1 1 d . . .
H4A H 0.4047 1.2241 0.0606 0.040 Uiso 1 1 calc R . .
C5 C 0.3986(4) 1.2659(3) 0.2014(3) 0.0318(7) Uani 1 1 d . . .
H5A H 0.3378 1.3197 0.1823 0.038 Uiso 1 1 calc R . .
C6 C 0.4450(4) 1.2456(2) 0.3016(2) 0.0272(6) Uani 1 1 d . . .
H6A H 0.4165 1.2841 0.3513 0.033 Uiso 1 1 calc R . .
C7 C 0.5349(4) 1.1666(2) 0.3258(2) 0.0231(6) Uani 1 1 d . . .
C8 C 0.6017(3) 1.1244(2) 0.4204(2) 0.0210(5) Uani 1 1 d . . .
C9 C 0.6375(3) 1.1230(2) 0.5932(2) 0.0209(5) Uani 1 1 d . . .
C10 C 0.6151(4) 1.1630(2) 0.6858(2) 0.0220(5) Uani 1 1 d . . .
C11 C 0.5349(4) 1.2425(2) 0.7040(2) 0.0261(6) Uani 1 1 d . . .
H11A H 0.4831 1.2803 0.6515 0.031 Uiso 1 1 calc R . .
C12 C 0.5339(4) 1.2640(2) 0.8023(3) 0.0298(7) Uani 1 1 d . . .
H12A H 0.4818 1.3184 0.8177 0.036 Uiso 1 1 calc R . .
C13 C 0.6078(4) 1.2073(3) 0.8786(2) 0.0307(7) Uani 1 1 d . . .
H13A H 0.6032 1.2236 0.9448 0.037 Uiso 1 1 calc R . .
C14 C 0.6880(4) 1.1278(2) 0.8616(2) 0.0276(6) Uani 1 1 d . . .
H14A H 0.7378 1.0897 0.9145 0.033 Uiso 1 1 calc R . .
C15 C 0.6921(4) 1.1064(2) 0.7628(2) 0.0222(5) Uani 1 1 d . . .
C16 C 0.7617(3) 1.0328(2) 0.7148(2) 0.0216(5) Uani 1 1 d . . .
C17 C 0.9115(3) 0.8911(2) 0.7149(2) 0.0215(5) Uani 1 1 d . . .
C18 C 0.9960(4) 0.8128(2) 0.7661(2) 0.0225(6) Uani 1 1 d . . .
C19 C 1.0282(4) 0.7819(2) 0.8640(2) 0.0281(6) Uani 1 1 d . . .
H19A H 0.9959 0.8162 0.9151 0.034 Uiso 1 1 calc R . .
C20 C 1.1092(4) 0.6990(3) 0.8834(3) 0.0319(7) Uani 1 1 d . . .
H20A H 1.1318 0.6761 0.9490 0.038 Uiso 1 1 calc R . .
C21 C 1.1588(4) 0.6481(3) 0.8090(3) 0.0348(7) Uani 1 1 d . . .
H21A H 1.2156 0.5922 0.8253 0.042 Uiso 1 1 calc R . .
C22 C 1.1258(4) 0.6785(2) 0.7118(3) 0.0327(7) Uani 1 1 d . . .
H22A H 1.1596 0.6447 0.6610 0.039 Uiso 1 1 calc R . .
C23 C 1.0415(4) 0.7602(2) 0.6914(2) 0.0242(6) Uani 1 1 d . . .
C24 C 0.9805(4) 0.8063(2) 0.5981(2) 0.0222(5) Uani 1 1 d . . .
C25 C 0.9435(4) 0.8087(2) 0.4255(2) 0.0223(6) Uani 1 1 d . . .
C26 C 0.9598(4) 0.7676(2) 0.3312(2) 0.0251(6) Uani 1 1 d . . .
C27 C 1.0335(4) 0.6864(2) 0.3085(3) 0.0313(7) Uani 1 1 d . . .
H27A H 1.0905 0.6486 0.3591 0.038 Uiso 1 1 calc R . .
C28 C 1.0196(5) 0.6634(3) 0.2086(3) 0.0364(8) Uani 1 1 d . . .
H28A H 1.0673 0.6083 0.1904 0.044 Uiso 1 1 calc R . .
C29 C 0.9364(5) 0.7199(3) 0.1338(3) 0.0353(7) Uani 1 1 d . . .
H29A H 0.9279 0.7015 0.0661 0.042 Uiso 1 1 calc R . .
C30 C 0.8666(4) 0.8018(3) 0.1561(2) 0.0302(7) Uani 1 1 d . . .
H30A H 0.8122 0.8407 0.1055 0.036 Uiso 1 1 calc R . .
C31 C 0.8797(4) 0.8246(2) 0.2566(2) 0.0245(6) Uani 1 1 d . . .
C32 C 0.8160(4) 0.9011(2) 0.3057(2) 0.0227(6) Uani 1 1 d . . .
C101 C 0.5391(5) 0.5117(4) 0.4074(3) 0.0427(17) Uiso 0.50 1 d PG A -1
C102 C 0.4017(6) 0.4939(4) 0.3288(3) 0.050(2) Uiso 0.50 1 d PG A -1
H10B H 0.4129 0.4991 0.2623 0.059 Uiso 0.50 1 calc PR A -1
C103 C 0.2480(5) 0.4684(4) 0.3476(3) 0.0455(18) Uiso 0.50 1 d PG A -1
H10C H 0.1541 0.4562 0.2939 0.055 Uiso 0.50 1 calc PR A -1
C104 C 0.2317(4) 0.4608(4) 0.4449(3) 0.0437(17) Uiso 0.50 1 d PG A -1
H10D H 0.1267 0.4433 0.4578 0.052 Uiso 0.50 1 calc PR A -1
C105 C 0.3691(4) 0.4786(3) 0.5235(3) 0.0417(17) Uiso 0.50 1 d PG A -1
C106 C 0.5228(4) 0.5041(3) 0.5048(3) 0.0470(16) Uiso 0.50 1 d PG A -1
C107 C 0.6602(5) 0.5220(5) 0.5834(4) 0.062(2) Uiso 0.50 1 d PG A -1
H10E H 0.7653 0.5394 0.5705 0.075 Uiso 0.50 1 calc PR A -1
C108 C 0.6439(7) 0.5143(5) 0.6807(3) 0.089(4) Uiso 0.50 1 d PG A -1
H10F H 0.7378 0.5265 0.7344 0.107 Uiso 0.50 1 calc PR A -1
C109 C 0.4902(8) 0.4888(5) 0.6995(2) 0.075(3) Uiso 0.50 1 d PG A -1
H10G H 0.4790 0.4836 0.7660 0.090 Uiso 0.50 1 calc PR A -1
C110 C 0.3528(6) 0.4710(4) 0.6209(3) 0.084(4) Uiso 0.50 1 d PG A -1
H11B H 0.2477 0.4536 0.6337 0.101 Uiso 0.50 1 calc PR A -1
BrS Br 0.72651(12) 0.55012(6) 0.35907(8) 0.0548(2) Uani 0.50 1 d P A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
_geom_angle_site_symmetry_3
Br1 I1 Br1 180.0 2_665
C1 N1 C8 107.8(2) .
C9 N2 C8 124.5(3) .
C16 N3 C9 109.0(2) .
C16 N4 C17 127.3(3) .
C17 N5 C24 107.2(2) .
C25 N6 C24 124.0(3) .
C25 N7 C32 110.0(2) .
C32 N8 C1 122.1(3) .
N8 C1 N1 127.8(3) .
N8 C1 C2 122.3(3) .
N1 C1 C2 109.9(3) .
C3 C2 C7 121.3(3) .
C3 C2 C1 132.6(3) .
C7 C2 C1 106.1(3) .
C4 C3 C2 116.9(3) .
C3 C4 C5 121.8(3) .
C6 C5 C4 121.3(3) .
C7 C6 C5 117.2(3) .
C6 C7 C2 121.5(3) .
C6 C7 C8 132.2(3) .
C2 C7 C8 106.3(3) .
N2 C8 N1 127.8(3) .
N2 C8 C7 122.3(3) .
N1 C8 C7 109.9(2) .
N2 C9 N3 128.6(3) .
N2 C9 C10 123.6(3) .
N3 C9 C10 107.8(2) .
C11 C10 C15 122.0(3) .
C11 C10 C9 130.2(3) .
C15 C10 C9 107.8(2) .
C12 C11 C10 117.1(3) .
C11 C12 C13 121.1(3) .
C14 C13 C12 122.5(3) .
C13 C14 C15 116.9(3) .
C14 C15 C10 120.4(3) .
C14 C15 C16 134.2(3) .
C10 C15 C16 105.4(2) .
N4 C16 N3 123.3(3) .
N4 C16 C15 126.8(3) .
N3 C16 C15 109.9(2) .
N5 C17 N4 123.3(3) .
N5 C17 C18 111.7(2) .
N4 C17 C18 125.0(3) .
C19 C18 C23 120.6(3) .
C19 C18 C17 134.6(3) .
C23 C18 C17 104.7(2) .
C20 C19 C18 117.2(3) .
C19 C20 C21 122.0(3) .
C22 C21 C20 120.7(3) .
C23 C22 C21 117.6(3) .
C22 C23 C18 121.8(3) .
C22 C23 C24 131.1(3) .
C18 C23 C24 107.1(2) .
N6 C24 N5 129.1(3) .
N6 C24 C23 121.7(3) .
N5 C24 C23 109.3(2) .
N6 C25 N7 128.0(3) .
N6 C25 C26 123.9(3) .
N7 C25 C26 108.0(3) .
C27 C26 C31 121.3(3) .
C27 C26 C25 131.6(3) .
C31 C26 C25 107.1(3) .
C28 C27 C26 117.1(3) .
C27 C28 C29 121.4(3) .
C30 C29 C28 121.7(3) .
C29 C30 C31 116.9(3) .
C30 C31 C26 121.6(3) .
C30 C31 C32 131.4(3) .
C26 C31 C32 106.9(3) .
N8 C32 N7 128.2(3) .
N8 C32 C31 123.9(3) .
N7 C32 C31 108.0(3) .
C102 C101 C106 120.0 .
C102 C101 BrS 110.1(2) .
C106 C101 BrS 129.8(2) .
C103 C102 C101 120.0 .
C104 C103 C102 120.0 .
C105 C104 C103 120.0 .
C106 C105 C104 120.0 .
C106 C105 C110 120.0 .
C104 C105 C110 120.0 .
C107 C106 C105 120.0 .
C107 C106 C101 120.0 .
C105 C106 C101 120.0 .
C108 C107 C106 120.0 .
C109 C108 C107 120.0 .
C108 C109 C110 120.0 .
C109 C110 C105 120.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 Br1 2.6986(4) .
I1 Br1 2.6986(4) 2_665
N1 C1 1.368(4) .
N1 C8 1.373(4) .
N2 C9 1.320(4) .
N2 C8 1.325(4) .
N3 C16 1.360(4) .
N3 C9 1.385(4) .
N4 C16 1.355(4) .
N4 C17 1.359(4) .
N5 C17 1.351(4) .
N5 C24 1.380(4) .
N6 C25 1.322(4) .
N6 C24 1.324(4) .
N7 C25 1.371(4) .
N7 C32 1.374(4) .
N8 C32 1.320(4) .
N8 C1 1.329(4) .
C1 C2 1.462(4) .
C2 C3 1.394(4) .
C2 C7 1.401(4) .
C3 C4 1.393(5) .
C4 C5 1.396(5) .
C5 C6 1.393(5) .
C6 C7 1.391(4) .
C7 C8 1.457(4) .
C9 C10 1.446(4) .
C10 C11 1.393(4) .
C10 C15 1.407(4) .
C11 C12 1.390(5) .
C12 C13 1.391(5) .
C13 C14 1.389(4) .
C14 C15 1.403(4) .
C15 C16 1.447(4) .
C17 C18 1.456(4) .
C18 C19 1.400(4) .
C18 C23 1.400(4) .
C19 C20 1.386(4) .
C20 C21 1.402(5) .
C21 C22 1.389(5) .
C22 C23 1.389(4) .
C23 C24 1.457(4) .
C25 C26 1.454(4) .
C26 C27 1.398(4) .
C26 C31 1.398(4) .
C27 C28 1.387(5) .
C28 C29 1.406(5) .
C29 C30 1.385(5) .
C30 C31 1.396(4) .
C31 C32 1.455(4) .
C101 C102 1.3900 .
C101 C106 1.3900 .
C101 BrS 1.881(3) .
C102 C103 1.3900 .
C103 C104 1.3900 .
C104 C105 1.3900 .
C105 C106 1.3900 .
C105 C110 1.3900 .
C106 C107 1.3900 .
C107 C108 1.3900 .
C108 C109 1.3900 .
C109 C110 1.3900 .
