#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:21:36 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301847 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/58/7015810.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_7015810
loop_
_publ_author_name
'Costa, Roshinee'
'Geier, 3rd, G Richard'
'Ziegler, Christopher J.'
_publ_section_title
;
 Structure and spectroscopic characterization of free base and metal
 complexes of 5,5-dimethyl-10,15-bis(pentafluorophenyl)isocorrole.
;
_journal_issue                   17
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4384
_journal_page_last               4386
_journal_paper_doi               10.1039/c1dt10112a
_journal_volume                  40
_journal_year                    2011
_chemical_formula_sum            'C34 H17 Cl3 F10 N4'
_chemical_formula_weight         777.87
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 90.472(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2762(12)
_cell_length_b                   11.2082(14)
_cell_length_c                   14.9861(19)
_cell_measurement_reflns_used    5343
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.27
_cell_volume                     1558.0(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12937
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_T_max  0.9368
_exptl_absorpt_correction_T_min  0.8759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS; Sheldrick, 2004 [Sheldrick, G. M. (2004)]
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         6661
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0331
_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)+(0.0411P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0792
_reflns_number_gt                5864
_reflns_number_total             6661
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10112a.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      P2(1)
_cod_database_code               7015810
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 0.2571(2) 1.2193(2) 0.83544(15) 0.0230(5) Uani 1 1 d . . .
C2 C 0.3180(2) 1.3321(2) 0.82297(15) 0.0249(5) Uani 1 1 d . . .
H2 H 0.3266 1.3729 0.7677 0.030 Uiso 1 1 calc R . .
C3 C 0.3643(3) 1.3742(2) 0.90657(16) 0.0270(5) Uani 1 1 d . . .
H3 H 0.4090 1.4488 0.9185 0.032 Uiso 1 1 calc R . .
C4 C 0.3322(2) 1.2853(2) 0.96914(14) 0.0206(4) Uani 1 1 d . . .
C5 C 0.3569(2) 1.2757(2) 1.06916(13) 0.0191(4) Uani 1 1 d . . .
C6 C 0.3226(2) 1.15276(19) 1.10895(14) 0.0190(4) Uani 1 1 d . . .
C7 C 0.3515(2) 1.1263(2) 1.20318(14) 0.0224(5) Uani 1 1 d . . .
H7 H 0.3899 1.1798 1.2464 0.027 Uiso 1 1 calc R . .
C8 C 0.3130(2) 1.0113(2) 1.21700(14) 0.0231(5) Uani 1 1 d . . .
H8 H 0.3203 0.9682 1.2714 0.028 Uiso 1 1 calc R . .
C9 C 0.2585(2) 0.96703(19) 1.13194(13) 0.0179(4) Uani 1 1 d . . .
C10 C 0.2079(2) 0.85134(19) 1.11629(13) 0.0175(4) Uani 1 1 d . . .
C11 C 0.1564(2) 0.80024(18) 1.03430(13) 0.0179(4) Uani 1 1 d . . .
C12 C 0.1091(2) 0.6827(2) 1.01730(14) 0.0197(4) Uani 1 1 d . . .
H12 H 0.0973 0.6216 1.0606 0.024 Uiso 1 1 calc R . .
C13 C 0.0829(2) 0.6720(2) 0.92654(14) 0.0201(5) Uani 1 1 d . . .
H13 H 0.0509 0.6022 0.8965 0.024 Uiso 1 1 calc R . .
C14 C 0.1122(2) 0.7826(2) 0.88688(13) 0.0187(4) Uani 1 1 d . . .
C15 C 0.1053(2) 0.8204(2) 0.79467(14) 0.0191(4) Uani 1 1 d . . .
C16 C 0.1348(2) 0.9366(2) 0.76836(14) 0.0214(5) Uani 1 1 d . . .
C17 C 0.1482(2) 0.9859(2) 0.67838(14) 0.0225(5) Uani 1 1 d . . .
H17 H 0.1300 0.9455 0.6237 0.027 Uiso 1 1 calc R . .
C18 C 0.1915(2) 1.1002(2) 0.68859(15) 0.0237(5) Uani 1 1 d . . .
H18 H 0.2097 1.1561 0.6424 0.028 Uiso 1 1 calc R . .
C19 C 0.2051(2) 1.1213(2) 0.78458(14) 0.0217(5) Uani 1 1 d . . .
C20 C 0.2601(3) 1.3699(2) 1.11456(16) 0.0254(5) Uani 1 1 d . . .
H20A H 0.2832 1.4493 1.0912 0.038 Uiso 1 1 calc R . .
H20B H 0.2774 1.3686 1.1792 0.038 Uiso 1 1 calc R . .
H20C H 0.1587 1.3516 1.1021 0.038 Uiso 1 1 calc R . .
C21 C 0.5169(2) 1.3041(2) 1.08940(15) 0.0272(5) Uani 1 1 d . . .
H21A H 0.5782 1.2442 1.0609 0.041 Uiso 1 1 calc R . .
H21B H 0.5335 1.3028 1.1541 0.041 Uiso 1 1 calc R . .
H21C H 0.5404 1.3834 1.0661 0.041 Uiso 1 1 calc R . .
C22 C 0.2130(2) 0.7678(2) 1.19483(13) 0.0184(4) Uani 1 1 d . . .
C23 C 0.1241(2) 0.7838(2) 1.26828(14) 0.0208(4) Uani 1 1 d . . .
C24 C 0.1349(2) 0.7136(2) 1.34323(14) 0.0237(5) Uani 1 1 d . . .
C25 C 0.2342(3) 0.6217(2) 1.34649(14) 0.0247(5) Uani 1 1 d . . .
C26 C 0.3235(3) 0.6023(2) 1.27455(15) 0.0240(5) Uani 1 1 d . . .
C27 C 0.3119(2) 0.67514(19) 1.20007(14) 0.0199(5) Uani 1 1 d . . .
C28 C 0.0708(2) 0.73134(19) 0.72431(13) 0.0191(4) Uani 1 1 d . . .
C29 C 0.1601(2) 0.6341(2) 0.70593(14) 0.0199(5) Uani 1 1 d . . .
C30 C 0.1337(2) 0.5558(2) 0.63768(14) 0.0227(5) Uani 1 1 d . . .
C31 C 0.0121(3) 0.5706(2) 0.58421(14) 0.0242(5) Uani 1 1 d . . .
C32 C -0.0780(2) 0.6653(2) 0.59934(15) 0.0231(5) Uani 1 1 d . . .
C33 C -0.0498(2) 0.7438(2) 0.66787(14) 0.0213(5) Uani 1 1 d . . .
C34 C 0.5070(3) 0.8572(2) 0.50951(16) 0.0277(5) Uani 1 1 d . . .
H34 H 0.6044 0.8853 0.5295 0.033 Uiso 1 1 calc R . .
Cl1 Cl 0.43283(8) 0.77008(7) 0.59512(4) 0.04460(17) Uani 1 1 d . . .
Cl2 Cl 0.52816(7) 0.77249(6) 0.41110(4) 0.03533(14) Uani 1 1 d . . .
Cl3 Cl 0.40042(9) 0.98229(6) 0.48706(5) 0.0520(2) Uani 1 1 d . . .
F1 F 0.02545(14) 0.87210(12) 1.26789(8) 0.0276(3) Uani 1 1 d . . .
F2 F 0.05156(14) 0.73519(12) 1.41487(8) 0.0312(3) Uani 1 1 d . . .
F3 F 0.24777(16) 0.55450(13) 1.42017(9) 0.0339(3) Uani 1 1 d . . .
F4 F 0.42402(15) 0.51649(12) 1.27946(9) 0.0317(3) Uani 1 1 d . . .
F5 F 0.40284(13) 0.65473(11) 1.13226(8) 0.0241(3) Uani 1 1 d . . .
F6 F 0.28168(13) 0.61894(11) 0.75477(8) 0.0254(3) Uani 1 1 d . . .
F7 F 0.22369(15) 0.46491(12) 0.62104(8) 0.0299(3) Uani 1 1 d . . .
F8 F -0.01618(15) 0.49263(13) 0.51860(8) 0.0338(3) Uani 1 1 d . . .
F9 F -0.19568(14) 0.68242(13) 0.54666(9) 0.0321(3) Uani 1 1 d . . .
F10 F -0.14061(13) 0.83591(12) 0.67891(8) 0.0267(3) Uani 1 1 d . . .
N1 N 0.2676(2) 1.19685(16) 0.92547(12) 0.0223(4) Uani 1 1 d . . .
H2A H 0.2352 1.1316 0.9511 0.027 Uiso 1 1 calc R . .
N2 N 0.26765(18) 1.05768(16) 1.06797(11) 0.0181(4) Uani 1 1 d . . .
N3 N 0.15403(18) 0.85850(16) 0.95405(11) 0.0171(4) Uani 1 1 d . . .
H4 H 0.1763 0.9341 0.9466 0.021 Uiso 1 1 calc R . .
N4 N 0.1678(2) 1.02346(16) 0.82993(11) 0.0220(4) Uani 1 1 d . . .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 C2 105.7(2) . . ?
N1 C1 C19 113.96(19) . . ?
C2 C1 C19 139.8(2) . . ?
C1 C2 C3 107.8(2) . . ?
C4 C3 C2 107.0(2) . . ?
N1 C4 C3 107.37(19) . . ?
N1 C4 C5 119.85(19) . . ?
C3 C4 C5 132.8(2) . . ?
C4 C5 C6 114.61(18) . . ?
C4 C5 C21 108.43(17) . . ?
C6 C5 C21 108.09(18) . . ?
C4 C5 C20 107.61(17) . . ?
C6 C5 C20 108.59(16) . . ?
C21 C5 C20 109.43(18) . . ?
N2 C6 C7 110.47(18) . . ?
N2 C6 C5 128.30(19) . . ?
C7 C6 C5 121.22(19) . . ?
C8 C7 C6 107.06(19) . . ?
C7 C8 C9 106.33(19) . . ?
C10 C9 N2 125.47(18) . . ?
C10 C9 C8 125.3(2) . . ?
N2 C9 C8 109.25(18) . . ?
C9 C10 C11 128.54(19) . . ?
C9 C10 C22 115.97(18) . . ?
C11 C10 C22 115.45(18) . . ?
N3 C11 C12 106.51(18) . . ?
N3 C11 C10 124.42(18) . . ?
C12 C11 C10 128.93(19) . . ?
C13 C12 C11 108.0(2) . . ?
C12 C13 C14 107.9(2) . . ?
N3 C14 C13 106.97(18) . . ?
N3 C14 C15 121.93(19) . . ?
C13 C14 C15 131.1(2) . . ?
C16 C15 C14 122.6(2) . . ?
C16 C15 C28 118.08(19) . . ?
C14 C15 C28 119.23(19) . . ?
N4 C16 C15 121.14(19) . . ?
N4 C16 C17 109.33(19) . . ?
C15 C16 C17 129.4(2) . . ?
C18 C17 C16 106.3(2) . . ?
C17 C18 C19 106.7(2) . . ?
N4 C19 C1 116.75(19) . . ?
N4 C19 C18 110.3(2) . . ?
C1 C19 C18 132.8(2) . . ?
C27 C22 C23 116.58(19) . . ?
C27 C22 C10 121.78(18) . . ?
C23 C22 C10 121.54(19) . . ?
F1 C23 C24 117.95(18) . . ?
F1 C23 C22 119.86(19) . . ?
C24 C23 C22 122.2(2) . . ?
F2 C24 C23 120.6(2) . . ?
F2 C24 C25 119.4(2) . . ?
C23 C24 C25 120.0(2) . . ?
F3 C25 C26 120.1(2) . . ?
F3 C25 C24 120.3(2) . . ?
C26 C25 C24 119.5(2) . . ?
F4 C26 C25 119.4(2) . . ?
F4 C26 C27 121.0(2) . . ?
C25 C26 C27 119.5(2) . . ?
F5 C27 C26 117.58(19) . . ?
F5 C27 C22 120.20(18) . . ?
C26 C27 C22 122.2(2) . . ?
C29 C28 C33 115.41(19) . . ?
C29 C28 C15 122.66(18) . . ?
C33 C28 C15 121.81(19) . . ?
F6 C29 C30 117.88(19) . . ?
F6 C29 C28 119.01(19) . . ?
C30 C29 C28 123.0(2) . . ?
F7 C30 C29 121.2(2) . . ?
F7 C30 C31 119.2(2) . . ?
C29 C30 C31 119.6(2) . . ?
F8 C31 C32 120.7(2) . . ?
F8 C31 C30 119.9(2) . . ?
C32 C31 C30 119.4(2) . . ?
F9 C32 C31 120.2(2) . . ?
F9 C32 C33 119.4(2) . . ?
C31 C32 C33 120.4(2) . . ?
F10 C33 C32 117.90(19) . . ?
F10 C33 C28 119.94(19) . . ?
C32 C33 C28 122.1(2) . . ?
Cl3 C34 Cl1 111.23(13) . . ?
Cl3 C34 Cl2 109.71(13) . . ?
Cl1 C34 Cl2 110.96(14) . . ?
C4 N1 C1 112.01(18) . . ?
C6 N2 C9 106.89(16) . . ?
C11 N3 C14 110.56(17) . . ?
C19 N4 C16 107.28(17) . . ?
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 1.375(3) . ?
C1 C2 1.398(3) . ?
C1 C19 1.419(3) . ?
C2 C3 1.403(3) . ?
C3 C4 1.402(3) . ?
C4 N1 1.328(3) . ?
C4 C5 1.518(3) . ?
C5 C6 1.536(3) . ?
C5 C21 1.545(3) . ?
C5 C20 1.547(3) . ?
C6 N2 1.329(3) . ?
C6 C7 1.465(3) . ?
C7 C8 1.354(3) . ?
C8 C9 1.455(3) . ?
C9 C10 1.398(3) . ?
C9 N2 1.400(3) . ?
C10 C11 1.434(3) . ?
C10 C22 1.505(3) . ?
C11 N3 1.369(3) . ?
C11 C12 1.411(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.402(3) . ?
C14 N3 1.372(3) . ?
C14 C15 1.447(3) . ?
C15 C16 1.388(3) . ?
C15 C28 1.485(3) . ?
C16 N4 1.374(3) . ?
C16 C17 1.463(3) . ?
C17 C18 1.352(3) . ?
C18 C19 1.462(3) . ?
C19 N4 1.337(3) . ?
C22 C27 1.387(3) . ?
C22 C23 1.392(3) . ?
C23 F1 1.348(2) . ?
C23 C24 1.375(3) . ?
C24 F2 1.350(2) . ?
C24 C25 1.382(3) . ?
C25 F3 1.341(3) . ?
C25 C26 1.382(3) . ?
C26 F4 1.341(3) . ?
C26 C27 1.386(3) . ?
C27 F5 1.346(2) . ?
C28 C29 1.397(3) . ?
C28 C33 1.404(3) . ?
C29 F6 1.350(2) . ?
C29 C30 1.369(3) . ?
C30 F7 1.341(3) . ?
C30 C31 1.388(3) . ?
C31 F8 1.339(3) . ?
C31 C32 1.371(3) . ?
C32 F9 1.355(2) . ?
C32 C33 1.375(3) . ?
C33 F10 1.344(2) . ?
C34 Cl3 1.747(3) . ?
C34 Cl1 1.757(2) . ?
C34 Cl2 1.766(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652821
2 PubChem 139156558
