#------------------------------------------------------------------------------
#$Date: 2019-11-25 06:36:55 +0100 (lun 25 de nov de 2019) $
#$Revision: 240386 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/97/4129718.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_4129718
loop_
_publ_author_name
'Furuyama, Taniyuki'
'Sato, Takehito'
'Kobayashi, Nagao'
_publ_section_title
;
 A Bottom-up Synthesis of Antiaromatic Expanded Phthalocyanines:
 Pentabenzotriazasmaragdyrins, i.e. Norcorroles of Superphthalocyanines.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13788
_journal_page_last               13791
_journal_paper_doi               10.1021/jacs.5b09853
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C24 H16 F12 N4 O4, 2(C H4 O)'
_chemical_formula_sum            'C26 H24 F12 N4 O6'
_chemical_formula_weight         716.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                91.9330(10)
_cell_angle_beta                 102.8530(10)
_cell_angle_gamma                91.4830(10)
_cell_formula_units_Z            1
_cell_length_a                   7.2292(6)
_cell_length_b                   8.3533(7)
_cell_length_c                   11.9019(10)
_cell_measurement_temperature    100(2)
_cell_volume                     699.91(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6694
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.441
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9664
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of Göttingen, Germany.'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0422P)²+0.3143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2296
_reflns_number_total             2453
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b09853_si_002.cif
_cod_data_source_block           test
_cod_database_code               4129718
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.983
_exptl_absorpt_special_details
; 
 SADABS (Sheldrick, 1997) 
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N -0.39056(16) -0.19924(13) 0.49851(10) 0.0151(2) Uani 1 1 d . .
C1 C -0.43065(18) -0.03725(16) 0.47941(11) 0.0139(3) Uani 1 1 d . .
C2 C -0.30273(18) 0.03023(16) 0.41152(11) 0.0142(3) Uani 1 1 d . .
C3 C -0.28412(19) 0.17831(16) 0.36343(11) 0.0151(3) Uani 1 1 d . .
H1 H -0.364(2) 0.265(2) 0.3714(13) 0.017(4) Uiso 1 1 d . .
C4 C -0.14729(19) 0.19724(16) 0.29995(11) 0.0159(3) Uani 1 1 d . .
C5 C -0.02645(19) 0.07227(17) 0.28495(11) 0.0162(3) Uani 1 1 d . .
C6 C -0.04241(19) -0.07453(17) 0.33347(11) 0.0156(3) Uani 1 1 d . .
H2 H 0.040(2) -0.155(2) 0.3255(13) 0.015(4) Uiso 1 1 d . .
C7 C -0.18367(18) -0.09253(16) 0.39506(11) 0.0146(3) Uani 1 1 d . .
C8 C -0.24457(18) -0.23143(16) 0.45187(11) 0.0148(3) Uani 1 1 d . .
N2 N -0.16550(18) -0.37425(15) 0.45450(11) 0.0186(3) Uani 1 1 d . .
H3 H -0.208(3) -0.452(2) 0.4920(17) 0.034(5) Uiso 1 1 d . .
O1 O -0.12541(14) 0.34627(11) 0.25564(8) 0.0186(2) Uani 1 1 d . .
C9 C -0.1586(2) 0.34976(18) 0.13341(12) 0.0222(3) Uani 1 1 d . .
H4 H -0.049(3) 0.323(2) 0.1054(15) 0.024(4) Uiso 1 1 d . .
C10 C -0.2093(2) 0.51674(18) 0.10055(13) 0.0220(3) Uani 1 1 d . .
H5 H 0.146(2) -0.118(2) 0.1692(14) 0.021(4) Uiso 1 1 d . .
H6 H -0.262(3) 0.277(2) 0.0965(16) 0.031(5) Uiso 1 1 d . .
H7 H 0.466(3) 0.517(3) 0.3251(19) 0.052(6) Uiso 1 1 d . .
H8 H -0.074(3) -0.390(2) 0.4206(15) 0.026(4) Uiso 1 1 d . .
F1 F -0.36816(15) 0.56229(14) 0.12847(9) 0.0452(3) Uani 1 1 d . .
F2 F -0.07352(15) 0.62485(11) 0.15012(9) 0.0362(3) Uani 1 1 d . .
F3 F -0.23204(14) 0.52912(12) -0.01363(8) 0.0329(2) Uani 1 1 d . .
O2 O 0.10250(14) 0.10758(11) 0.21919(8) 0.0193(2) Uani 1 1 d . .
C11 C 0.2190(2) -0.01862(18) 0.19890(13) 0.0198(3) Uani 1 1 d . .
H9 H 0.312(3) -0.040(2) 0.2679(16) 0.025(4) Uiso 1 1 d . .
C12 C 0.3190(2) 0.03395(18) 0.10778(13) 0.0212(3) Uani 1 1 d . .
F4 F 0.41366(12) 0.17428(11) 0.13422(8) 0.0287(2) Uani 1 1 d . .
F5 F 0.20016(13) 0.04911(12) 0.00567(7) 0.0314(2) Uani 1 1 d . .
F6 F 0.44373(14) -0.07614(12) 0.09339(9) 0.0366(3) Uani 1 1 d . .
C13 C 0.3331(2) 0.5311(2) 0.30720(14) 0.0239(3) Uani 1 1 d . .
H10 H 0.271(3) 0.434(3) 0.2941(19) 0.050(6) Uiso 1 1 d . .
H11 H 0.313(3) 0.596(3) 0.238(2) 0.057(6) Uiso 1 1 d . .
O3 O 0.27546(14) 0.61374(12) 0.40058(9) 0.0207(2) Uani 1 1 d . .
H12 H 0.3665 0.6717 0.4382 0.031 Uiso 1 1 calc R U
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'
F F 0.0171 0.0103 '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
C8 N1 C1 106.88(11) .
C1 C1 N1 122.25(15) 2_456
C1 C1 C2 128.37(16) 2_456
N1 C1 C2 109.38(11) .
C7 C2 C3 119.62(12) .
C7 C2 C1 105.85(11) .
C3 C2 C1 134.51(12) .
C4 C3 C2 118.24(13) .
C3 C4 O1 117.90(12) .
C3 C4 C5 121.50(13) .
O1 C4 C5 120.52(12) .
O2 C5 C6 124.07(12) .
O2 C5 C4 115.25(12) .
C6 C5 C4 120.67(12) .
C5 C6 C7 117.02(13) .
C6 C7 C2 122.93(13) .
C6 C7 C8 131.17(12) .
C2 C7 C8 105.89(11) .
N1 C8 N2 123.79(13) .
N1 C8 C7 111.95(12) .
N2 C8 C7 124.25(12) .
C4 O1 C9 115.77(10) .
O1 C9 C10 107.40(12) .
F1 C10 F2 106.72(13) .
F1 C10 F3 107.62(12) .
F2 C10 F3 106.55(12) .
F1 C10 C9 113.32(13) .
F2 C10 C9 112.34(12) .
F3 C10 C9 109.95(12) .
C5 O2 C11 116.01(11) .
O2 C11 C12 107.11(12) .
F4 C12 F5 106.52(12) .
F4 C12 F6 107.82(11) .
F5 C12 F6 107.34(12) .
F4 C12 C11 113.26(12) .
F5 C12 C11 112.61(12) .
F6 C12 C11 109.02(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C8 1.3265(18) .
N1 C1 1.4066(18) .
C1 C1 1.365(3) 2_456
C1 C2 1.4704(18) .
C2 C7 1.3921(19) .
C2 C3 1.3961(19) .
C3 C4 1.3808(19) .
C4 O1 1.3871(17) .
C4 C5 1.410(2) .
C5 O2 1.3764(16) .
C5 C6 1.386(2) .
C6 C7 1.3911(19) .
C7 C8 1.4684(19) .
C8 N2 1.3345(18) .
O1 C9 1.4223(17) .
C9 C10 1.494(2) .
C10 F1 1.3256(17) .
C10 F2 1.3372(18) .
C10 F3 1.3400(17) .
O2 C11 1.4134(17) .
C11 C12 1.5021(19) .
C12 F4 1.3339(18) .
C12 F5 1.3350(17) .
C12 F6 1.3377(17) .
C13 O3 1.4331(18) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C8 N1 C1 C1 -177.38(16) . 2_456
C8 N1 C1 C2 2.57(14) . .
C1 C1 C2 C7 177.85(17) 2_456 .
N1 C1 C2 C7 -2.09(14) . .
C1 C1 C2 C3 -3.8(3) 2_456 .
N1 C1 C2 C3 176.26(14) . .
C7 C2 C3 C4 0.40(19) . .
C1 C2 C3 C4 -177.78(14) . .
C2 C3 C4 O1 -177.91(11) . .
C2 C3 C4 C5 -1.0(2) . .
C3 C4 C5 O2 179.67(12) . .
O1 C4 C5 O2 -3.53(18) . .
C3 C4 C5 C6 0.3(2) . .
O1 C4 C5 C6 177.11(12) . .
O2 C5 C6 C7 -178.28(12) . .
C4 C5 C6 C7 1.03(19) . .
C5 C6 C7 C2 -1.7(2) . .
C5 C6 C7 C8 176.81(13) . .
C3 C2 C7 C6 1.0(2) . .
C1 C2 C7 C6 179.65(12) . .
C3 C2 C7 C8 -177.83(12) . .
C1 C2 C7 C8 0.82(14) . .
C1 N1 C8 N2 179.20(12) . .
C1 N1 C8 C7 -2.08(15) . .
C6 C7 C8 N1 -177.92(13) . .
C2 C7 C8 N1 0.78(15) . .
C6 C7 C8 N2 0.8(2) . .
C2 C7 C8 N2 179.49(13) . .
C3 C4 O1 C9 -118.91(14) . .
C5 C4 O1 C9 64.18(17) . .
C4 O1 C9 C10 156.48(12) . .
O1 C9 C10 F1 -62.91(16) . .
O1 C9 C10 F2 58.15(16) . .
O1 C9 C10 F3 176.63(11) . .
C6 C5 O2 C11 2.10(19) . .
C4 C5 O2 C11 -177.24(12) . .
C5 O2 C11 C12 168.89(11) . .
O2 C11 C12 F4 54.44(15) . .
O2 C11 C12 F5 -66.51(16) . .
O2 C11 C12 F6 174.47(11) . .
