#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:19:44 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180257 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/43/7114307.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_7114307
loop_
_publ_author_name
'Liu, Wei'
'Lee, Chi-Hang'
'Li, Hung-Wing'
'Lam, Chi-Keung'
'Wang, Jinzhi'
'Mak, Thomas C. W.'
'Ng, Dennis K. P.'
_publ_section_title
;
 Formation and crystal structure of an unexpected inclusion complex of a
 metal-free phthalocyanine and oxalic acidElectronic supplementary
 information (ESI) available: experimental procedure to prepare compound 3
 and its characterising data. See
 http://www.rsc.org/suppdata/cc/b1/b111133g/
;
_journal_issue                   6
_journal_name_full               'Chemical Communications'
_journal_page_first              628
_journal_paper_doi               10.1039/b111133g
_journal_year                    2002
_chemical_formula_sum            'C62 H76 N8 O8'
_chemical_formula_weight         1061.31
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.911(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.8962(15)
_cell_length_b                   8.8141(9)
_cell_length_c                   21.695(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2994.3(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD 1K'
_diffrn_measurement_method       'omega 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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13406
_diffrn_reflns_theta_full        23.00
_diffrn_reflns_theta_max         23.00
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rhombic plate'
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0030(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0686
_refine_ls_shift/su_max          0.588
_refine_ls_shift/su_mean         0.022
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1436P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1996
_refine_ls_wR_factor_ref         0.2195
_reflns_number_gt                2594
_reflns_number_total             4160
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b111133g.txt
_cod_data_source_block           eu
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2994.4(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7114307
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N1 N 0.62220(17) -0.0281(3) 0.49583(12) 0.0504(7) Uani 1 1 d .
H1 H 0.561(3) -0.0009(16) 0.4993(2) 0.25(3) Uiso 1 1 d R
O1 O 0.63255(15) 0.3163(3) 0.29127(11) 0.0694(8) Uani 1 1 d .
C1 C 0.4118(2) 0.1916(4) 0.39600(14) 0.0464(8) Uani 1 1 d .
N2 N 0.62989(16) 0.1164(3) 0.40187(12) 0.0510(7) Uani 1 1 d .
O2 O 0.15702(15) 0.2809(3) 0.41544(13) 0.0810(9) Uani 1 1 d .
C2 C 0.4268(2) 0.2771(4) 0.34196(14) 0.0470(8) Uani 1 1 d .
N3 N 0.48591(16) 0.1238(3) 0.42354(12) 0.0475(7) Uani 1 1 d .
C3 C 0.3723(2) 0.3632(4) 0.29884(16) 0.0608(10) Uani 1 1 d .
H3B H 0.3148 0.3739 0.3015 0.073 Uiso 1 1 calc R
N4 N 0.33642(17) 0.1900(3) 0.41408(12) 0.0519(8) Uani 1 1 d .
C4 C 0.4069(2) 0.4328(4) 0.25162(17) 0.0672(11) Uani 1 1 d .
H4C H 0.3719 0.4905 0.2217 0.081 Uiso 1 1 calc R
C5 C 0.4923(2) 0.4177(4) 0.24834(17) 0.0649(11) Uani 1 1 d .
H5A H 0.5130 0.4647 0.2156 0.078 Uiso 1 1 calc R
C6 C 0.5485(2) 0.3356(4) 0.29155(16) 0.0526(9) Uani 1 1 d .
C7 C 0.5132(2) 0.2612(4) 0.33878(14) 0.0451(8) Uani 1 1 d .
C8 C 0.5490(2) 0.1621(4) 0.39039(14) 0.0456(8) Uani 1 1 d .
C9 C 0.6619(2) 0.0283(4) 0.44984(15) 0.0501(9) Uani 1 1 d .
C10 C 0.7485(2) -0.0259(4) 0.45954(16) 0.0568(9) Uani 1 1 d .
C11 C 0.8136(2) -0.0036(5) 0.4250(2) 0.0803(13) Uani 1 1 d .
H11A H 0.8058 0.0564 0.3892 0.096 Uiso 1 1 calc R
C12 C 0.8897(3) -0.0741(6) 0.4463(2) 0.1010(17) Uani 1 1 d .
H12A H 0.9343 -0.0617 0.4241 0.121 Uiso 1 1 calc R
C13 C 0.3208(2) 0.1163(4) 0.46474(15) 0.0504(9) Uani 1 1 d .
C14 C 0.2404(2) 0.1177(4) 0.48708(16) 0.0543(9) Uani 1 1 d .
C15 C 0.1618(2) 0.1901(5) 0.46662(18) 0.0686(11) Uani 1 1 d .
C16 C 0.0972(3) 0.1637(5) 0.5002(2) 0.0913(15) Uani 1 1 d .
H16A H 0.0437 0.2066 0.4868 0.110 Uiso 1 1 calc R
C17 C 0.0867(2) 0.3822(5) 0.39516(19) 0.0763(12) Uani 1 1 d .
H17A H 0.0431 0.3650 0.4213 0.092 Uiso 1 1 calc R
C18 C 0.1192(3) 0.5439(6) 0.4054(2) 0.0991(15) Uani 1 1 d .
H18A H 0.1649 0.5592 0.3810 0.119 Uiso 1 1 calc R
C19 C 0.1549(6) 0.5728(9) 0.4733(3) 0.205(4) Uani 1 1 d .
H19A H 0.1995 0.5009 0.4874 0.307 Uiso 1 1 calc R
H19B H 0.1104 0.5621 0.4977 0.307 Uiso 1 1 calc R
H19C H 0.1778 0.6738 0.4780 0.307 Uiso 1 1 calc R
C20 C 0.0506(5) 0.6607(7) 0.3851(3) 0.156(3) Uani 1 1 d .
H20A H 0.0745 0.7606 0.3921 0.233 Uiso 1 1 calc R
H20B H 0.0055 0.6481 0.4090 0.233 Uiso 1 1 calc R
H20C H 0.0281 0.6478 0.3415 0.233 Uiso 1 1 calc R
C21 C 0.0493(3) 0.3388(6) 0.3279(2) 0.0897(14) Uani 1 1 d .
H21A H 0.0018 0.4081 0.3136 0.108 Uiso 1 1 calc R
C22 C 0.0130(4) 0.1786(7) 0.3255(3) 0.140(2) Uani 1 1 d .
H22A H -0.0273 0.1710 0.3536 0.210 Uiso 1 1 calc R
H22B H 0.0585 0.1074 0.3376 0.210 Uiso 1 1 calc R
H22C H -0.0152 0.1566 0.2836 0.210 Uiso 1 1 calc R
C23 C 0.1124(3) 0.3553(7) 0.2841(2) 0.1139(18) Uani 1 1 d .
H23A H 0.1342 0.4571 0.2864 0.171 Uiso 1 1 calc R
H23B H 0.0846 0.3341 0.2421 0.171 Uiso 1 1 calc R
H23C H 0.1586 0.2854 0.2959 0.171 Uiso 1 1 calc R
C24 C 0.6828(3) 0.4256(5) 0.2625(2) 0.0848(14) Uani 1 1 d .
H24A H 0.6443 0.4988 0.2381 0.102 Uiso 1 1 calc R
C25 C 0.7287(4) 0.3381(8) 0.2194(3) 0.125(2) Uani 1 1 d .
H25A H 0.7570 0.2511 0.2422 0.150 Uiso 1 1 calc R
C26 C 0.7917(5) 0.4199(10) 0.1895(4) 0.195(4) Uani 1 1 d .
H26A H 0.8354 0.4610 0.2212 0.293 Uiso 1 1 calc R
H26B H 0.7639 0.5008 0.1643 0.293 Uiso 1 1 calc R
H26C H 0.8170 0.3511 0.1636 0.293 Uiso 1 1 calc R
C27 C 0.6633(6) 0.2793(9) 0.1650(3) 0.163(3) Uani 1 1 d .
H27A H 0.6919 0.2218 0.1372 0.245 Uiso 1 1 calc R
H27B H 0.6340 0.3634 0.1428 0.245 Uiso 1 1 calc R
H27C H 0.6229 0.2155 0.1807 0.245 Uiso 1 1 calc R
C28 C 0.7386(4) 0.5077(8) 0.3161(4) 0.138(2) Uani 1 1 d .
H28A H 0.7708 0.5840 0.2969 0.165 Uiso 1 1 calc R
C29 C 0.8048(4) 0.4012(11) 0.3532(4) 0.200(4) Uani 1 1 d .
H29A H 0.8366 0.3519 0.3251 0.300 Uiso 1 1 calc R
H29B H 0.7763 0.3263 0.3742 0.300 Uiso 1 1 calc R
H29C H 0.8430 0.4587 0.3835 0.300 Uiso 1 1 calc R
C30 C 0.6874(6) 0.5924(9) 0.3560(4) 0.191(4) Uani 1 1 d .
H30A H 0.6485 0.6593 0.3304 0.286 Uiso 1 1 calc R
H30B H 0.7249 0.6505 0.3866 0.286 Uiso 1 1 calc R
H30C H 0.6558 0.5218 0.3769 0.286 Uiso 1 1 calc R
O3 O 0.3849(5) 0.5685(10) 0.4884(3) 0.219(3) Uani 1 1 d .
O4 O 0.5165(5) 0.6436(11) 0.4454(4) 0.267(5) Uani 1 1 d .
C31 C 0.4574(8) 0.5363(14) 0.4789(9) 0.236(7) Uani 1 1 d .
H4 H 0.5142(8) 0.6876(16) 0.3998(7) 0.014(6) Uiso 1 1 d R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C9 N1 C13 108.8(3) . 3_656
C6 O1 C24 122.3(3) . .
N4 C1 N3 128.6(3) . .
N4 C1 C2 122.0(3) . .
N3 C1 C2 109.5(3) . .
C9 N2 C8 123.5(3) . .
C15 O2 C17 123.1(3) . .
C3 C2 C7 121.9(3) . .
C3 C2 C1 131.3(3) . .
C7 C2 C1 106.8(3) . .
C1 N3 C8 108.4(3) . .
C4 C3 C2 117.3(3) . .
C1 N4 C13 123.7(3) . .
C5 C4 C3 121.0(3) . .
C4 C5 C6 122.9(3) . .
O1 C6 C5 126.0(3) . .
O1 C6 C7 117.5(3) . .
C5 C6 C7 116.4(3) . .
C2 C7 C6 120.5(3) . .
C2 C7 C8 106.2(3) . .
C6 C7 C8 133.3(3) . .
N2 C8 N3 126.7(3) . .
N2 C8 C7 124.2(3) . .
N3 C8 C7 109.1(3) . .
N2 C9 N1 128.6(3) . .
N2 C9 C10 122.5(3) . .
N1 C9 C10 108.9(3) . .
C11 C10 C14 121.8(3) . 3_656
C11 C10 C9 131.0(3) . .
C14 C10 C9 107.2(3) 3_656 .
C12 C11 C10 116.7(4) . .
C11 C12 C16 122.6(4) . 3_656
N4 C13 N1 126.2(3) . 3_656
N4 C13 C14 125.0(3) . .
N1 C13 C14 108.9(3) 3_656 .
C10 C14 C15 120.2(3) 3_656 .
C10 C14 C13 106.2(3) 3_656 .
C15 C14 C13 133.5(3) . .
O2 C15 C16 126.1(3) . .
O2 C15 C14 116.5(3) . .
C16 C15 C14 117.3(3) . .
C15 C16 C12 121.3(4) . 3_656
O2 C17 C18 108.1(4) . .
O2 C17 C21 106.9(3) . .
C18 C17 C21 116.2(4) . .
C19 C18 C20 107.6(5) . .
C19 C18 C17 111.3(5) . .
C20 C18 C17 112.8(5) . .
C23 C21 C22 111.0(5) . .
C23 C21 C17 112.9(4) . .
C22 C21 C17 110.4(4) . .
O1 C24 C25 106.8(4) . .
O1 C24 C28 106.1(4) . .
C25 C24 C28 116.2(5) . .
C26 C25 C24 117.7(6) . .
C26 C25 C27 104.6(6) . .
C24 C25 C27 108.6(5) . .
C30 C28 C24 112.3(5) . .
C30 C28 C29 113.3(7) . .
C24 C28 C29 111.6(6) . .
O3 C31 O4 125.3(13) . .
O3 C31 C31 135(3) . 3_666
O4 C31 C31 89.4(14) . 3_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C9 1.363(4) .
N1 C13 1.375(4) 3_656
O1 C6 1.348(4) .
O1 C24 1.459(4) .
C1 N4 1.324(4) .
C1 N3 1.363(4) .
C1 C2 1.448(4) .
N2 C9 1.328(4) .
N2 C8 1.330(4) .
O2 C15 1.360(4) .
O2 C17 1.439(4) .
C2 C3 1.387(5) .
C2 C7 1.394(4) .
N3 C8 1.373(4) .
C3 C4 1.386(5) .
N4 C13 1.337(4) .
C4 C5 1.378(5) .
C5 C6 1.382(5) .
C6 C7 1.411(4) .
C7 C8 1.456(4) .
C9 C10 1.438(4) .
C10 C11 1.393(4) .
C10 C14 1.399(4) 3_656
C11 C12 1.367(6) .
C12 C16 1.389(6) 3_656
C13 N1 1.375(4) 3_656
C13 C14 1.443(4) .
C14 C10 1.399(4) 3_656
C14 C15 1.405(5) .
C15 C16 1.378(5) .
C16 C12 1.389(6) 3_656
C17 C18 1.520(6) .
C17 C21 1.525(6) .
C18 C19 1.507(8) .
C18 C20 1.509(7) .
C21 C23 1.502(6) .
C21 C22 1.523(7) .
C24 C25 1.496(7) .
C24 C28 1.519(8) .
C25 C26 1.471(8) .
C25 C27 1.523(9) .
C28 C30 1.488(9) .
C28 C29 1.532(8) .
O3 C31 1.238(13) .
O4 C31 1.59(2) .
C31 C31 1.63(2) 3_666
