#------------------------------------------------------------------------------
#$Date: 2014-07-12 07:06:18 +0300 (Sat, 12 Jul 2014) $
#$Revision: 120112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/25/7052598.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_7052598
loop_
_publ_author_name
'Costa, Roshinee'
'Schick, Andrew J.'
'Paul, Nathan B.'
'Durfee, William S.'
'Ziegler, Christopher J.'
_publ_section_title
;
 Hydroxybenziphthalocyanines: non-aromatic phthalocyanine analogues
 that exhibit strong UV-visible absorptions
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              794
_journal_volume                  35
_journal_year                    2011
_chemical_formula_sum            'C24 H25.4 N6 O2.7'
_chemical_formula_weight         441.16
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.881(3)
_cell_angle_beta                 101.751(3)
_cell_angle_gamma                93.578(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6457(16)
_cell_length_b                   9.891(2)
_cell_length_c                   15.431(3)
_cell_measurement_reflns_used    3687
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.31
_cell_volume                     1126.8(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9095
_diffrn_reflns_theta_full        26.75
_diffrn_reflns_theta_max         26.75
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9741
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_platon_squeeze_details
;
;
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0902P)^2^+0.1014P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1511
_reflns_number_gt                3688
_reflns_number_total             4686
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    c0nj00500b.txt
_[local]_cod_data_source_block   5
_[local]_cod_cif_authors_sg_H-M  P-1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_database_code               7052598
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
C1 C 0.1810(2) 0.22398(17) 0.05670(11) 0.0231(4) Uani 1 1 d . . .
C2 C 0.1945(2) 0.09841(17) -0.00448(11) 0.0236(4) Uani 1 1 d . . .
C3 C 0.1356(2) 0.05962(19) -0.09605(12) 0.0292(4) Uani 1 1 d . . .
H3 H 0.0738 0.1191 -0.1325 0.035 Uiso 1 1 calc R . .
C4 C 0.1703(3) -0.0699(2) -0.13260(12) 0.0335(4) Uani 1 1 d . . .
H4 H 0.1317 -0.0995 -0.1952 0.040 Uiso 1 1 calc R . .
C5 C 0.2601(3) -0.15657(19) -0.07943(12) 0.0325(4) Uani 1 1 d . . .
H5 H 0.2816 -0.2445 -0.1063 0.039 Uiso 1 1 calc R . .
C6 C 0.3197(2) -0.11758(18) 0.01268(12) 0.0275(4) Uani 1 1 d . . .
H6 H 0.3817 -0.1770 0.0491 0.033 Uiso 1 1 calc R . .
C7 C 0.2849(2) 0.01114(17) 0.04902(11) 0.0227(4) Uani 1 1 d . . .
C8 C 0.3271(2) 0.08439(16) 0.14243(11) 0.0208(3) Uani 1 1 d . . .
C9 C 0.5510(2) 0.24286(16) 0.31170(10) 0.0193(3) Uani 1 1 d . . .
H9 H 0.5897 0.2768 0.2634 0.023 Uiso 1 1 calc R . .
C10 C 0.4480(2) 0.11740(16) 0.29658(10) 0.0192(3) Uani 1 1 d . . .
C11 C 0.3944(2) 0.06617(16) 0.36763(11) 0.0216(3) Uani 1 1 d . . .
H11 H 0.3273 -0.0207 0.3579 0.026 Uiso 1 1 calc R . .
C12 C 0.4393(2) 0.14262(17) 0.45278(11) 0.0233(4) Uani 1 1 d . . .
H12 H 0.3997 0.1087 0.5009 0.028 Uiso 1 1 calc R . .
C13 C 0.5413(2) 0.26788(16) 0.46849(11) 0.0209(3) Uani 1 1 d . . .
H13 H 0.5728 0.3187 0.5272 0.025 Uiso 1 1 calc R . .
C14 C 0.5977(2) 0.31923(16) 0.39774(10) 0.0187(3) Uani 1 1 d . . .
C15 C 0.6695(2) 0.54342(16) 0.37529(10) 0.0190(3) Uani 1 1 d . . .
C16 C 0.7873(2) 0.67175(15) 0.38713(10) 0.0185(3) Uani 1 1 d . . .
C17 C 0.9581(2) 0.71172(16) 0.43822(11) 0.0218(4) Uani 1 1 d . . .
H17 H 1.0206 0.6533 0.4752 0.026 Uiso 1 1 calc R . .
C18 C 1.0343(2) 0.84058(17) 0.43319(11) 0.0251(4) Uani 1 1 d . . .
H18 H 1.1507 0.8715 0.4682 0.030 Uiso 1 1 calc R . .
C19 C 0.9438(2) 0.92604(17) 0.37780(12) 0.0259(4) Uani 1 1 d . . .
H19 H 1.0004 1.0132 0.3752 0.031 Uiso 1 1 calc R . .
C20 C 0.7723(2) 0.88551(16) 0.32654(11) 0.0221(4) Uani 1 1 d . . .
H20 H 0.7101 0.9433 0.2889 0.026 Uiso 1 1 calc R . .
C21 C 0.6956(2) 0.75764(16) 0.33253(10) 0.0192(3) Uani 1 1 d . . .
C22 C 0.5194(2) 0.68297(16) 0.28742(10) 0.0200(3) Uani 1 1 d . . .
C23 C 0.1086(2) 0.36130(19) 0.34161(12) 0.0316(4) Uani 1 1 d . . .
H23A H 0.1496 0.2735 0.3561 0.047 Uiso 1 1 calc R . .
H23B H -0.0223 0.3515 0.3215 0.047 Uiso 1 1 calc R . .
H23C H 0.1436 0.4313 0.3950 0.047 Uiso 1 1 calc R . .
C24 C 0.9316(3) 0.6016(2) 0.18610(14) 0.0365(5) Uani 1 1 d . . .
H24A H 0.8980 0.5064 0.1917 0.055 Uiso 1 1 calc R . .
H24B H 0.8251 0.6425 0.1580 0.055 Uiso 1 1 calc R . .
H24C H 0.9818 0.6537 0.2457 0.055 Uiso 1 1 calc R . .
N1 N 0.10266(19) 0.33080(15) 0.03381(10) 0.0281(3) Uani 1 1 d . . .
H1A H 0.0997 0.4014 0.0748 0.034 Uiso 1 1 calc R . .
H1B H 0.0526 0.3324 -0.0226 0.034 Uiso 1 1 calc R . .
N2 N 0.26139(18) 0.21226(14) 0.14177(9) 0.0225(3) Uani 1 1 d . . .
N3 N 0.40687(18) 0.03374(13) 0.21053(9) 0.0212(3) Uani 1 1 d . . .
N4 N 0.71161(17) 0.44220(13) 0.41660(9) 0.0196(3) Uani 1 1 d . . .
N5 N 0.51171(17) 0.55726(13) 0.31417(9) 0.0205(3) Uani 1 1 d . . .
H5A H 0.4206 0.4940 0.2956 0.025 Uiso 1 1 calc PR . .
N6 N 0.39210(19) 0.72592(14) 0.23251(9) 0.0256(3) Uani 1 1 d . . .
H6A H 0.4053 0.8083 0.2179 0.031 Uiso 1 1 calc R . .
O1 O 0.18851(15) 0.40131(12) 0.27214(8) 0.0250(3) Uani 1 1 d . . .
H1 H 0.230(3) 0.323(2) 0.2366(14) 0.037 Uiso 1 1 d . . .
O2 O 1.06170(15) 0.60460(13) 0.13234(8) 0.0283(3) Uani 1 1 d . . .
H2 H 1.1542 0.6537 0.1614 0.042 Uiso 1 1 calc R . .
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
C1 0.0217(8) 0.0264(9) 0.0217(8) 0.0056(7) 0.0050(7) 0.0005(6)
C2 0.0234(8) 0.0258(9) 0.0219(9) 0.0038(7) 0.0071(7) -0.0022(7)
C3 0.0316(9) 0.0329(10) 0.0213(9) 0.0052(7) 0.0036(7) -0.0055(7)
C4 0.0409(11) 0.0373(11) 0.0195(9) -0.0010(8) 0.0082(8) -0.0108(8)
C5 0.0423(11) 0.0258(9) 0.0292(10) -0.0031(7) 0.0150(8) -0.0060(8)
C6 0.0308(9) 0.0246(9) 0.0275(9) 0.0018(7) 0.0097(7) -0.0013(7)
C7 0.0212(8) 0.0262(9) 0.0205(9) 0.0034(7) 0.0058(7) -0.0021(6)
C8 0.0198(8) 0.0216(8) 0.0211(8) 0.0029(6) 0.0058(6) -0.0005(6)
C9 0.0208(8) 0.0208(8) 0.0181(8) 0.0071(6) 0.0043(6) 0.0054(6)
C10 0.0184(8) 0.0195(8) 0.0201(8) 0.0036(6) 0.0032(6) 0.0064(6)
C11 0.0232(8) 0.0163(8) 0.0267(9) 0.0056(6) 0.0066(7) 0.0035(6)
C12 0.0268(9) 0.0245(9) 0.0233(9) 0.0104(7) 0.0102(7) 0.0069(7)
C13 0.0245(8) 0.0226(8) 0.0167(8) 0.0036(6) 0.0051(6) 0.0067(6)
C14 0.0175(7) 0.0177(8) 0.0220(8) 0.0054(6) 0.0035(6) 0.0067(6)
C15 0.0186(8) 0.0210(8) 0.0170(8) 0.0010(6) 0.0042(6) 0.0027(6)
C16 0.0220(8) 0.0185(8) 0.0163(8) 0.0019(6) 0.0071(6) 0.0033(6)
C17 0.0213(8) 0.0222(8) 0.0217(8) 0.0030(6) 0.0037(6) 0.0048(6)
C18 0.0198(8) 0.0256(9) 0.0280(9) 0.0023(7) 0.0026(7) 0.0005(7)
C19 0.0249(9) 0.0205(8) 0.0332(10) 0.0049(7) 0.0085(7) 0.0003(7)
C20 0.0235(8) 0.0204(8) 0.0240(9) 0.0050(6) 0.0072(7) 0.0045(6)
C21 0.0207(8) 0.0203(8) 0.0178(8) 0.0019(6) 0.0069(6) 0.0047(6)
C22 0.0240(8) 0.0188(8) 0.0180(8) 0.0012(6) 0.0071(6) 0.0026(6)
C23 0.0343(10) 0.0335(10) 0.0304(10) 0.0062(8) 0.0126(8) 0.0080(8)
C24 0.0359(10) 0.0434(12) 0.0373(11) 0.0142(9) 0.0158(9) 0.0145(9)
N1 0.0309(8) 0.0304(8) 0.0228(8) 0.0073(6) 0.0019(6) 0.0075(6)
N2 0.0217(7) 0.0260(7) 0.0206(7) 0.0062(6) 0.0032(6) 0.0057(6)
N3 0.0230(7) 0.0198(7) 0.0203(7) 0.0029(5) 0.0044(5) 0.0002(5)
N4 0.0213(7) 0.0191(7) 0.0184(7) 0.0035(5) 0.0037(5) 0.0032(5)
N5 0.0216(7) 0.0177(7) 0.0211(7) 0.0043(5) 0.0014(5) 0.0019(5)
N6 0.0267(7) 0.0202(7) 0.0276(8) 0.0057(6) -0.0009(6) 0.0016(6)
O1 0.0251(6) 0.0238(6) 0.0264(7) 0.0030(5) 0.0065(5) 0.0036(5)
O2 0.0242(6) 0.0352(7) 0.0234(6) 0.0033(5) 0.0016(5) 0.0013(5)
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
_geom_angle_publ_flag
N1 C1 N2 124.16(16) . . ?
N1 C1 C2 125.83(16) . . ?
N2 C1 C2 110.00(14) . . ?
C3 C2 C7 121.34(16) . . ?
C3 C2 C1 132.63(16) . . ?
C7 C2 C1 106.02(14) . . ?
C2 C3 C4 117.38(17) . . ?
C5 C4 C3 121.25(17) . . ?
C4 C5 C6 121.42(17) . . ?
C7 C6 C5 117.32(17) . . ?
C6 C7 C2 121.29(16) . . ?
C6 C7 C8 131.68(16) . . ?
C2 C7 C8 107.03(14) . . ?
N3 C8 N2 127.58(15) . . ?
N3 C8 C7 124.46(15) . . ?
N2 C8 C7 107.94(13) . . ?
C10 C9 C14 120.33(14) . . ?
C11 C10 C9 119.90(15) . . ?
C11 C10 N3 118.43(14) . . ?
C9 C10 N3 121.49(14) . . ?
C12 C11 C10 119.70(15) . . ?
C13 C12 C11 120.82(15) . . ?
C12 C13 C14 119.83(15) . . ?
C13 C14 C9 119.40(15) . . ?
C13 C14 N4 118.66(14) . . ?
C9 C14 N4 121.78(14) . . ?
N4 C15 N5 128.96(15) . . ?
N4 C15 C16 123.62(14) . . ?
N5 C15 C16 107.41(13) . . ?
C17 C16 C21 121.31(15) . . ?
C17 C16 C15 131.56(14) . . ?
C21 C16 C15 107.12(14) . . ?
C16 C17 C18 117.27(15) . . ?
C17 C18 C19 121.53(15) . . ?
C20 C19 C18 121.03(15) . . ?
C21 C20 C19 117.32(15) . . ?
C20 C21 C16 121.53(15) . . ?
C20 C21 C22 131.42(14) . . ?
C16 C21 C22 107.04(14) . . ?
N6 C22 N5 124.35(15) . . ?
N6 C22 C21 127.48(15) . . ?
N5 C22 C21 108.17(13) . . ?
C1 N2 C8 109.00(14) . . ?
C8 N3 C10 119.04(14) . . ?
C15 N4 C14 120.59(13) . . ?
C22 N5 C15 110.24(14) . . ?
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
C1 N1 1.302(2) . ?
C1 N2 1.355(2) . ?
C1 C2 1.476(2) . ?
C2 C3 1.385(2) . ?
C2 C7 1.393(2) . ?
C3 C4 1.391(3) . ?
C4 C5 1.384(3) . ?
C5 C6 1.393(2) . ?
C6 C7 1.383(2) . ?
C7 C8 1.484(2) . ?
C8 N3 1.284(2) . ?
C8 N2 1.390(2) . ?
C9 C10 1.392(2) . ?
C9 C14 1.400(2) . ?
C10 C11 1.392(2) . ?
C10 N3 1.429(2) . ?
C11 C12 1.388(2) . ?
C12 C13 1.386(2) . ?
C13 C14 1.397(2) . ?
C14 N4 1.411(2) . ?
C15 N4 1.282(2) . ?
C15 N5 1.3988(19) . ?
C15 C16 1.477(2) . ?
C16 C17 1.383(2) . ?
C16 C21 1.397(2) . ?
C17 C18 1.387(2) . ?
C18 C19 1.398(2) . ?
C19 C20 1.390(2) . ?
C20 C21 1.383(2) . ?
C21 C22 1.483(2) . ?
C22 N6 1.288(2) . ?
C22 N5 1.364(2) . ?
C23 O1 1.425(2) . ?
C24 O2 1.421(2) . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.500 0.000 76 14 ' '
_journal_paper_doi 10.1039/c0nj00500b