#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/25/7052597.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_7052597
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_paper_doi               10.1039/c0nj00500b
_journal_volume                  35
_journal_year                    2011
_chemical_formula_sum            'C45 H34 N10 O2'
_chemical_formula_weight         746.82
_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                114.123(3)
_cell_angle_beta                 100.136(4)
_cell_angle_gamma                97.330(4)
_cell_formula_units_Z            2
_cell_length_a                   11.751(3)
_cell_length_b                   12.885(3)
_cell_length_c                   13.632(3)
_cell_measurement_reflns_used    3819
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.55
_cell_volume                     1808.1(7)
_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 0.972
_diffrn_measured_fraction_theta_max 0.972
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15267
_diffrn_reflns_theta_full        27.25
_diffrn_reflns_theta_max         27.25
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         7879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0639
_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)+(0.1068P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1871
_reflns_number_gt                5606
_reflns_number_total             7879
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0nj00500b.txt
_cod_data_source_block           4
_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 

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        1808.0(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7052597
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 0.20414(17) 1.09309(17) 1.12847(16) 0.0255(4) Uani 1 1 d . . .
C2 C 0.12271(17) 1.10974(17) 1.20227(16) 0.0268(4) Uani 1 1 d . . .
C3 C 0.11724(19) 1.20123(18) 1.29975(17) 0.0313(5) Uani 1 1 d . . .
H3 H 0.1763 1.2717 1.3347 0.038 Uiso 1 1 calc R . .
C4 C 0.02239(19) 1.18618(19) 1.34454(17) 0.0339(5) Uani 1 1 d . . .
H4 H 0.0174 1.2466 1.4121 0.041 Uiso 1 1 calc R . .
C5 C -0.06601(19) 1.08309(19) 1.29139(17) 0.0329(5) Uani 1 1 d . . .
H5 H -0.1308 1.0752 1.3228 0.039 Uiso 1 1 calc R . .
C6 C -0.06029(18) 0.99232(18) 1.19356(17) 0.0308(5) Uani 1 1 d . . .
H6 H -0.1211 0.9232 1.1567 0.037 Uiso 1 1 calc R . .
C7 C 0.03663(17) 1.00526(17) 1.15099(16) 0.0270(4) Uani 1 1 d . . .
C8 C 0.07296(17) 0.92840(17) 1.05353(16) 0.0266(4) Uani 1 1 d . . .
C9 C 0.04063(17) 0.74953(17) 0.89455(16) 0.0273(4) Uani 1 1 d . . .
C10 C -0.03063(18) 0.63918(17) 0.81711(17) 0.0298(4) Uani 1 1 d . . .
C11 C -0.14139(19) 0.5788(2) 0.8099(2) 0.0386(5) Uani 1 1 d . . .
H11 H -0.1827 0.6096 0.8656 0.046 Uiso 1 1 calc R . .
C12 C -0.1890(2) 0.4717(2) 0.7181(2) 0.0429(6) Uani 1 1 d . . .
H12 H -0.2643 0.4286 0.7112 0.051 Uiso 1 1 calc R . .
C13 C -0.1280(2) 0.4249(2) 0.6342(2) 0.0431(6) Uani 1 1 d . . .
H13 H -0.1634 0.3513 0.5727 0.052 Uiso 1 1 calc R . .
C14 C -0.01907(19) 0.48382(19) 0.64013(19) 0.0386(5) Uani 1 1 d . . .
H14 H 0.0207 0.4521 0.5833 0.046 Uiso 1 1 calc R . .
C15 C 0.03164(18) 0.59142(18) 0.73170(18) 0.0342(5) Uani 1 1 d . . .
C16 C 0.13741(17) 0.67422(17) 0.75896(17) 0.0289(4) Uani 1 1 d . . .
C17 C 0.30751(17) 0.74224(17) 0.71485(16) 0.0279(4) Uani 1 1 d . . .
C18 C 0.39188(17) 0.72379(17) 0.64493(16) 0.0271(4) Uani 1 1 d . . .
C19 C 0.40049(19) 0.62743(18) 0.55246(17) 0.0322(5) Uani 1 1 d . . .
H19 H 0.3445 0.5553 0.5226 0.039 Uiso 1 1 calc R . .
C20 C 0.49355(19) 0.64040(19) 0.50543(17) 0.0348(5) Uani 1 1 d . . .
H20 H 0.5011 0.5760 0.4421 0.042 Uiso 1 1 calc R . .
C21 C 0.57642(19) 0.74610(19) 0.54919(17) 0.0341(5) Uani 1 1 d . . .
H21 H 0.6395 0.7524 0.5155 0.041 Uiso 1 1 calc R . .
C22 C 0.56755(18) 0.84244(18) 0.64185(17) 0.0309(5) Uani 1 1 d . . .
H22 H 0.6236 0.9145 0.6721 0.037 Uiso 1 1 calc R . .
C23 C 0.47405(18) 0.82940(17) 0.68839(16) 0.0285(4) Uani 1 1 d . . .
C24 C 0.43452(17) 0.90831(17) 0.78369(16) 0.0261(4) Uani 1 1 d . . .
C25 C 0.38618(17) 1.09354(17) 0.99194(16) 0.0264(4) Uani 1 1 d . . .
H25 H 0.3356 1.0190 0.9657 0.032 Uiso 1 1 calc R . .
C26 C 0.47170(17) 1.10947(16) 0.93751(16) 0.0263(4) Uani 1 1 d . . .
C27 C 0.54544(17) 1.21903(17) 0.97501(16) 0.0278(4) Uani 1 1 d . . .
C28 C 0.53526(17) 1.31233(17) 1.06902(16) 0.0278(4) Uani 1 1 d . . .
H28 H 0.5867 1.3865 1.0957 0.033 Uiso 1 1 calc R . .
C29 C 0.45056(17) 1.29764(16) 1.12389(16) 0.0267(4) Uani 1 1 d . . .
C30 C 0.37544(17) 1.18792(17) 1.08533(16) 0.0260(4) Uani 1 1 d . . .
C31 C 0.1273(2) 0.9007(3) 0.3718(2) 0.0579(7) Uani 1 1 d . . .
H31 H 0.0524 0.9163 0.3507 0.069 Uiso 1 1 calc R . .
C32 C 0.1922(2) 0.8648(2) 0.2934(2) 0.0496(6) Uani 1 1 d . . .
H32 H 0.1623 0.8553 0.2201 0.060 Uiso 1 1 calc R . .
C33 C 0.2999(2) 0.8433(2) 0.3237(2) 0.0543(7) Uani 1 1 d . . .
H33 H 0.3460 0.8172 0.2713 0.065 Uiso 1 1 calc R . .
C34 C 0.3415(3) 0.8598(3) 0.4310(2) 0.0597(7) Uani 1 1 d . . .
H34 H 0.4176 0.8478 0.4549 0.072 Uiso 1 1 calc R . .
C35 C 0.2697(3) 0.8941(2) 0.5030(2) 0.0556(7) Uani 1 1 d . . .
H35 H 0.2977 0.9036 0.5766 0.067 Uiso 1 1 calc R . .
C36 C 0.5577(2) 0.68035(19) 0.26067(18) 0.0388(5) Uani 1 1 d . . .
H36 H 0.4763 0.6716 0.2289 0.047 Uiso 1 1 calc R . .
C37 C 0.6335(2) 0.7867(2) 0.2965(2) 0.0436(6) Uani 1 1 d . . .
H37 H 0.6048 0.8493 0.2887 0.052 Uiso 1 1 calc R . .
C38 C 0.7518(2) 0.8008(2) 0.3441(2) 0.0431(6) Uani 1 1 d . . .
H38 H 0.8058 0.8737 0.3713 0.052 Uiso 1 1 calc R . .
C39 C 0.7895(2) 0.7064(2) 0.35109(19) 0.0407(5) Uani 1 1 d . . .
H39 H 0.8707 0.7129 0.3818 0.049 Uiso 1 1 calc R . .
C40 C 0.7086(2) 0.60295(19) 0.31316(18) 0.0369(5) Uani 1 1 d . . .
H40 H 0.7356 0.5387 0.3189 0.044 Uiso 1 1 calc R . .
C41 C 0.69190(19) 0.54331(19) 0.00515(18) 0.0339(5) Uani 1 1 d . . .
H41 H 0.6104 0.5313 -0.0286 0.041 Uiso 1 1 calc R . .
C42 C 0.75792(19) 0.65585(19) 0.06414(18) 0.0357(5) Uani 1 1 d . . .
H42 H 0.7229 0.7201 0.0704 0.043 Uiso 1 1 calc R . .
C43 C 0.8766(2) 0.67359(19) 0.11419(19) 0.0391(5) Uani 1 1 d . . .
H43 H 0.9247 0.7503 0.1550 0.047 Uiso 1 1 calc R . .
C44 C 0.9238(2) 0.5783(2) 0.10388(19) 0.0403(5) Uani 1 1 d . . .
H44 H 1.0046 0.5879 0.1385 0.048 Uiso 1 1 calc R . .
C45 C 0.8513(2) 0.4690(2) 0.0422(2) 0.0393(5) Uani 1 1 d . . .
H45 H 0.8846 0.4034 0.0343 0.047 Uiso 1 1 calc R . .
H1N H 0.2985(19) 1.243(2) 1.204(2) 0.037(6) Uiso 1 1 d . . .
H4N H 0.192(2) 0.826(2) 0.889(2) 0.041(7) Uiso 1 1 d . . .
H7N H 0.561(2) 1.043(2) 0.828(2) 0.042(7) Uiso 1 1 d . . .
N1 N 0.29205(14) 1.18139(15) 1.14665(14) 0.0268(4) Uani 1 1 d . . .
N2 N 0.17814(14) 0.98717(14) 1.04467(13) 0.0265(4) Uani 1 1 d . . .
N3 N 0.01189(14) 0.82334(14) 0.98707(13) 0.0275(4) Uani 1 1 d . . .
N4 N 0.13935(16) 0.76722(16) 0.85709(14) 0.0287(4) Uani 1 1 d . . .
N5 N 0.21737(14) 0.66024(14) 0.69619(14) 0.0297(4) Uani 1 1 d . . .
N6 N 0.33818(14) 0.85743(14) 0.79869(13) 0.0278(4) Uani 1 1 d . . .
N7 N 0.49221(15) 1.02041(14) 0.84385(13) 0.0276(4) Uani 1 1 d . . .
N8 N 0.1642(2) 0.91451(19) 0.47534(19) 0.0557(6) Uani 1 1 d . . .
N9 N 0.59303(16) 0.58872(15) 0.26839(14) 0.0360(4) Uani 1 1 d . . .
N10 N 0.73729(16) 0.44972(15) -0.00694(15) 0.0344(4) Uani 1 1 d . . .
O1 O 0.43465(12) 1.38685(12) 1.21534(11) 0.0325(3) Uani 1 1 d . . .
H1 H 0.4832 1.4485 1.2309 0.049 Uiso 1 1 calc R . .
O2 O 0.62519(12) 1.22817(12) 0.91538(12) 0.0345(4) Uani 1 1 d . . .
H2 H 0.6649 1.2971 0.9445 0.052 Uiso 1 1 calc 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
_geom_angle_publ_flag
N2 C1 N1 125.63(18) . . ?
N2 C1 C2 113.60(17) . . ?
N1 C1 C2 120.74(18) . . ?
C3 C2 C7 121.42(19) . . ?
C3 C2 C1 134.15(19) . . ?
C7 C2 C1 104.41(17) . . ?
C2 C3 C4 117.7(2) . . ?
C3 C4 C5 120.94(19) . . ?
C6 C5 C4 120.94(19) . . ?
C7 C6 C5 118.2(2) . . ?
C6 C7 C2 120.61(18) . . ?
C6 C7 C8 133.07(19) . . ?
C2 C7 C8 106.31(17) . . ?
N3 C8 N2 127.67(18) . . ?
N3 C8 C7 122.26(18) . . ?
N2 C8 C7 110.06(17) . . ?
N3 C9 N4 128.03(18) . . ?
N3 C9 C10 124.60(18) . . ?
N4 C9 C10 107.35(18) . . ?
C11 C10 C9 132.5(2) . . ?
C11 C10 C15 120.9(2) . . ?
C9 C10 C15 106.48(18) . . ?
C12 C11 C10 117.4(2) . . ?
C11 C12 C13 121.7(2) . . ?
C14 C13 C12 121.5(2) . . ?
C13 C14 C15 118.3(2) . . ?
C14 C15 C16 131.8(2) . . ?
C14 C15 C10 120.2(2) . . ?
C16 C15 C10 107.82(19) . . ?
N5 C16 N4 129.16(18) . . ?
N5 C16 C15 124.39(19) . . ?
N4 C16 C15 106.45(18) . . ?
N5 C17 N6 127.47(18) . . ?
N5 C17 C18 122.33(18) . . ?
N6 C17 C18 110.19(17) . . ?
C19 C18 C23 120.97(19) . . ?
C19 C18 C17 132.76(19) . . ?
C23 C18 C17 106.26(17) . . ?
C20 C19 C18 117.7(2) . . ?
C19 C20 C21 121.44(19) . . ?
C22 C21 C20 120.71(19) . . ?
C23 C22 C21 117.7(2) . . ?
C22 C23 C18 121.45(18) . . ?
C22 C23 C24 133.97(19) . . ?
C18 C23 C24 104.58(17) . . ?
N6 C24 N7 125.90(18) . . ?
N6 C24 C23 113.18(17) . . ?
N7 C24 C23 120.90(18) . . ?
C26 C25 C30 119.44(18) . . ?
C25 C26 C27 120.49(18) . . ?
C25 C26 N7 124.51(18) . . ?
C27 C26 N7 115.00(17) . . ?
O2 C27 C28 123.33(18) . . ?
O2 C27 C26 116.94(17) . . ?
C28 C27 C26 119.73(18) . . ?
C29 C28 C27 120.32(18) . . ?
O1 C29 C28 122.92(18) . . ?
O1 C29 C30 117.15(17) . . ?
C28 C29 C30 119.93(17) . . ?
C25 C30 C29 120.07(18) . . ?
C25 C30 N1 124.07(18) . . ?
C29 C30 N1 115.85(17) . . ?
N8 C31 C32 123.5(2) . . ?
C33 C32 C31 118.3(2) . . ?
C32 C33 C34 119.3(2) . . ?
C33 C34 C35 118.2(3) . . ?
N8 C35 C34 123.7(2) . . ?
N9 C36 C37 123.3(2) . . ?
C36 C37 C38 118.9(2) . . ?
C39 C38 C37 118.3(2) . . ?
C40 C39 C38 119.4(2) . . ?
N9 C40 C39 122.8(2) . . ?
N10 C41 C42 123.0(2) . . ?
C41 C42 C43 118.6(2) . . ?
C44 C43 C42 118.9(2) . . ?
C45 C44 C43 118.4(2) . . ?
N10 C45 C44 123.8(2) . . ?
C1 N1 C30 130.77(17) . . ?
C1 N2 C8 105.45(16) . . ?
C8 N3 C9 124.48(18) . . ?
C9 N4 C16 111.89(18) . . ?
C17 N5 C16 123.95(18) . . ?
C24 N6 C17 105.79(16) . . ?
C24 N7 C26 130.53(18) . . ?
C35 N8 C31 116.9(2) . . ?
C36 N9 C40 117.28(19) . . ?
C45 N10 C41 117.26(19) . . ?
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 N2 1.326(2) . ?
C1 N1 1.343(3) . ?
C1 C2 1.479(3) . ?
C2 C3 1.389(3) . ?
C2 C7 1.399(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.402(3) . ?
C5 C6 1.388(3) . ?
C6 C7 1.387(3) . ?
C7 C8 1.470(3) . ?
C8 N3 1.300(3) . ?
C8 N2 1.416(2) . ?
C9 N3 1.364(3) . ?
C9 N4 1.376(2) . ?
C9 C10 1.413(3) . ?
C10 C11 1.394(3) . ?
C10 C15 1.449(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.421(3) . ?
C13 C14 1.374(3) . ?
C14 C15 1.396(3) . ?
C15 C16 1.413(3) . ?
C16 N5 1.359(3) . ?
C16 N4 1.378(3) . ?
C17 N5 1.305(3) . ?
C17 N6 1.404(2) . ?
C17 C18 1.468(3) . ?
C18 C19 1.392(3) . ?
C18 C23 1.393(3) . ?
C19 C20 1.386(3) . ?
C20 C21 1.397(3) . ?
C21 C22 1.395(3) . ?
C22 C23 1.387(3) . ?
C23 C24 1.480(3) . ?
C24 N6 1.325(2) . ?
C24 N7 1.343(3) . ?
C25 C26 1.392(3) . ?
C25 C30 1.395(3) . ?
C26 C27 1.395(3) . ?
C26 N7 1.409(2) . ?
C27 O2 1.368(2) . ?
C27 C28 1.390(3) . ?
C28 C29 1.384(3) . ?
C29 O1 1.370(2) . ?
C29 C30 1.402(3) . ?
C30 N1 1.411(2) . ?
C31 N8 1.331(3) . ?
C31 C32 1.383(4) . ?
C32 C33 1.359(4) . ?
C33 C34 1.375(4) . ?
C34 C35 1.379(4) . ?
C35 N8 1.322(3) . ?
C36 N9 1.337(3) . ?
C36 C37 1.378(3) . ?
C37 C38 1.381(3) . ?
C38 C39 1.380(3) . ?
C39 C40 1.374(3) . ?
C40 N9 1.343(3) . ?
C41 N10 1.341(3) . ?
C41 C42 1.375(3) . ?
C42 C43 1.386(3) . ?
C43 C44 1.377(3) . ?
C44 C45 1.375(3) . ?
C45 N10 1.330(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652937
2 PubChem 139175980
