#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:21:36 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301847 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/58/7015811.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_7015811
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 H15 Cl3 Cu F10 N4'
_chemical_formula_weight         839.39
_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                 90.678(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2791(19)
_cell_length_b                   11.191(2)
_cell_length_c                   14.859(3)
_cell_measurement_reflns_used    6106
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.74
_cell_measurement_theta_min      2.19
_cell_volume                     1542.9(5)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0543
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_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            12967
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    1.064
_exptl_absorpt_correction_T_max  0.9011
_exptl_absorpt_correction_T_min  0.7408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS; Sheldrick, 2004 [Sheldrick, G. M. (2004)]
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             834
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         6616
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0302
_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)+(0.0266P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0671
_reflns_number_gt                5914
_reflns_number_total             6616
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10112a.txt
_cod_data_source_block           Cu1
_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_cell_volume        1542.9(6)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7015811
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 0.2637(3) 1.2587(2) 0.83115(18) 0.0209(6) Uani 1 1 d . . .
C2 C 0.3233(3) 1.3741(2) 0.82218(19) 0.0242(6) Uani 1 1 d . . .
H2 H 0.3321 1.4183 0.7679 0.029 Uiso 1 1 calc R . .
C3 C 0.3663(3) 1.4106(3) 0.90675(19) 0.0257(6) Uani 1 1 d . . .
H3 H 0.4102 1.4846 0.9221 0.031 Uiso 1 1 calc R . .
C4 C 0.3318(3) 1.3149(2) 0.96724(18) 0.0182(5) Uani 1 1 d . . .
C5 C 0.3555(3) 1.3074(2) 1.06731(17) 0.0174(5) Uani 1 1 d . . .
C6 C 0.3219(3) 1.1879(2) 1.11160(17) 0.0182(5) Uani 1 1 d . . .
C7 C 0.3494(3) 1.1636(2) 1.20452(18) 0.0222(6) Uani 1 1 d . . .
H7 H 0.3876 1.2179 1.2478 0.027 Uiso 1 1 calc R . .
C8 C 0.3107(3) 1.0485(3) 1.21956(17) 0.0219(6) Uani 1 1 d . . .
H8 H 0.3179 1.0073 1.2753 0.026 Uiso 1 1 calc R . .
C9 C 0.2574(3) 1.0007(2) 1.13706(17) 0.0178(5) Uani 1 1 d . . .
C10 C 0.2075(3) 0.8854(2) 1.11902(17) 0.0163(5) Uani 1 1 d . . .
C11 C 0.1586(3) 0.8382(2) 1.03597(16) 0.0161(5) Uani 1 1 d . . .
C12 C 0.1134(3) 0.7199(2) 1.01646(18) 0.0182(6) Uani 1 1 d . . .
H12 H 0.1026 0.6568 1.0586 0.022 Uiso 1 1 calc R . .
C13 C 0.0883(3) 0.7135(2) 0.92619(17) 0.0181(6) Uani 1 1 d . . .
H13 H 0.0573 0.6449 0.8937 0.022 Uiso 1 1 calc R . .
C14 C 0.1172(3) 0.8284(2) 0.88928(17) 0.0162(5) Uani 1 1 d . . .
C15 C 0.1088(3) 0.8632(2) 0.79659(17) 0.0177(5) Uani 1 1 d . . .
C16 C 0.1379(3) 0.9772(2) 0.76643(17) 0.0182(6) Uani 1 1 d . . .
C17 C 0.1487(3) 1.0255(3) 0.67575(18) 0.0214(6) Uani 1 1 d . . .
H17 H 0.1279 0.9840 0.6214 0.026 Uiso 1 1 calc R . .
C18 C 0.1931(3) 1.1387(3) 0.68258(18) 0.0215(6) Uani 1 1 d . . .
H18 H 0.2105 1.1920 0.6342 0.026 Uiso 1 1 calc R . .
C19 C 0.2099(3) 1.1650(2) 0.77784(18) 0.0200(6) Uani 1 1 d . . .
C20 C 0.5142(3) 1.3392(3) 1.08872(19) 0.0251(6) Uani 1 1 d . . .
H20C H 0.5353 1.4194 1.0659 0.038 Uiso 1 1 calc R . .
H20A H 0.5776 1.2810 1.0599 0.038 Uiso 1 1 calc R . .
H20B H 0.5303 1.3373 1.1540 0.038 Uiso 1 1 calc R . .
C21 C 0.2575(3) 1.4049(2) 1.10951(19) 0.0232(6) Uani 1 1 d . . .
H21C H 0.1562 1.3859 1.0967 0.035 Uiso 1 1 calc R . .
H21A H 0.2808 1.4829 1.0836 0.035 Uiso 1 1 calc R . .
H21B H 0.2737 1.4072 1.1748 0.035 Uiso 1 1 calc R . .
C22 C 0.2125(3) 0.8013(2) 1.19770(17) 0.0167(5) Uani 1 1 d . . .
C23 C 0.1246(3) 0.8170(2) 1.27180(18) 0.0190(5) Uani 1 1 d . . .
C24 C 0.1361(3) 0.7466(3) 1.34745(18) 0.0204(6) Uani 1 1 d . . .
C25 C 0.2333(3) 0.6552(2) 1.34980(18) 0.0223(6) Uani 1 1 d . . .
C26 C 0.3213(3) 0.6355(2) 1.27763(18) 0.0211(6) Uani 1 1 d . . .
C27 C 0.3106(3) 0.7077(2) 1.20304(18) 0.0192(6) Uani 1 1 d . . .
C28 C 0.0717(3) 0.7718(2) 0.72721(17) 0.0184(6) Uani 1 1 d . . .
C29 C -0.0495(3) 0.7844(2) 0.67151(18) 0.0205(6) Uani 1 1 d . . .
C30 C -0.0811(3) 0.7045(3) 0.60366(17) 0.0208(6) Uani 1 1 d . . .
C31 C 0.0078(3) 0.6098(2) 0.58807(17) 0.0216(6) Uani 1 1 d . . .
C32 C 0.1308(3) 0.5953(2) 0.64075(17) 0.0200(6) Uani 1 1 d . . .
C33 C 0.1599(3) 0.6756(2) 0.70848(17) 0.0203(6) Uani 1 1 d . . .
C34 C 0.4935(3) 0.3951(3) 0.49185(19) 0.0257(6) Uani 1 1 d . . .
H34 H 0.3955 0.4201 0.4703 0.031 Uiso 1 1 calc R . .
Cl1 Cl 0.47384(8) 0.31334(7) 0.59109(5) 0.03359(18) Uani 1 1 d . . .
Cl2 Cl 0.59505(11) 0.52333(7) 0.51225(6) 0.0457(2) Uani 1 1 d . . .
Cl3 Cl 0.57241(10) 0.30739(8) 0.40741(6) 0.0453(2) Uani 1 1 d . . .
Cu1 Cu 0.21193(3) 1.06839(3) 0.949411(18) 0.01585(7) Uani 1 1 d . . .
F1 F 0.02684(17) 0.90531(14) 1.27160(10) 0.0252(4) Uani 1 1 d . . .
F2 F 0.05322(18) 0.76876(15) 1.41914(10) 0.0283(4) Uani 1 1 d . . .
F3 F 0.24619(17) 0.58730(14) 1.42379(10) 0.0297(4) Uani 1 1 d . . .
F4 F 0.42023(17) 0.54752(14) 1.28199(10) 0.0290(4) Uani 1 1 d . . .
F5 F 0.40036(16) 0.68754(14) 1.13480(10) 0.0230(3) Uani 1 1 d . . .
F6 F -0.14016(17) 0.87593(14) 0.68262(11) 0.0246(4) Uani 1 1 d . . .
F7 F -0.19956(17) 0.72058(15) 0.55178(10) 0.0295(4) Uani 1 1 d . . .
F8 F -0.02155(18) 0.53132(14) 0.52325(10) 0.0305(4) Uani 1 1 d . . .
F9 F 0.22092(18) 0.50538(14) 0.62388(10) 0.0276(4) Uani 1 1 d . . .
F10 F 0.28330(16) 0.66087(14) 0.75642(10) 0.0246(4) Uani 1 1 d . . .
N1 N 0.2714(2) 1.22794(19) 0.92121(14) 0.0183(5) Uani 1 1 d . . .
N2 N 0.2664(2) 1.09028(18) 1.07233(13) 0.0160(5) Uani 1 1 d . . .
N3 N 0.1569(2) 0.90373(19) 0.95796(14) 0.0154(4) Uani 1 1 d . . .
N4 N 0.1715(2) 1.0662(2) 0.82396(12) 0.0192(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'
Cu Cu 0.3201 1.2651 '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 C19 112.0(2) . . ?
N1 C1 C2 107.7(2) . . ?
C19 C1 C2 140.2(3) . . ?
C3 C2 C1 107.1(3) . . ?
C2 C3 C4 106.6(2) . . ?
N1 C4 C3 108.9(2) . . ?
N1 C4 C5 122.1(2) . . ?
C3 C4 C5 129.0(2) . . ?
C4 C5 C6 116.6(2) . . ?
C4 C5 C20 108.6(2) . . ?
C6 C5 C20 108.2(2) . . ?
C4 C5 C21 106.3(2) . . ?
C6 C5 C21 108.5(2) . . ?
C20 C5 C21 108.4(2) . . ?
N2 C6 C7 109.2(2) . . ?
N2 C6 C5 127.4(2) . . ?
C7 C6 C5 123.4(2) . . ?
C8 C7 C6 107.2(2) . . ?
C7 C8 C9 107.8(2) . . ?
N2 C9 C10 123.7(2) . . ?
N2 C9 C8 107.5(2) . . ?
C10 C9 C8 128.7(2) . . ?
C9 C10 C11 128.0(2) . . ?
C9 C10 C22 115.0(2) . . ?
C11 C10 C22 116.9(2) . . ?
N3 C11 C10 122.6(2) . . ?
N3 C11 C12 109.0(2) . . ?
C10 C11 C12 128.2(2) . . ?
C13 C12 C11 107.3(2) . . ?
C12 C13 C14 107.6(2) . . ?
N3 C14 C13 108.6(2) . . ?
N3 C14 C15 124.0(2) . . ?
C13 C14 C15 127.4(2) . . ?
C16 C15 C14 123.7(2) . . ?
C16 C15 C28 117.0(2) . . ?
C14 C15 C28 119.2(2) . . ?
N4 C16 C15 121.5(2) . . ?
N4 C16 C17 107.1(2) . . ?
C15 C16 C17 131.3(3) . . ?
C18 C17 C16 107.9(3) . . ?
C17 C18 C19 107.2(3) . . ?
N4 C19 C1 114.8(2) . . ?
N4 C19 C18 107.6(2) . . ?
C1 C19 C18 137.4(3) . . ?
C23 C22 C27 116.2(2) . . ?
C23 C22 C10 121.6(2) . . ?
C27 C22 C10 122.1(2) . . ?
F1 C23 C24 118.0(2) . . ?
F1 C23 C22 119.7(2) . . ?
C24 C23 C22 122.3(2) . . ?
F2 C24 C25 120.1(2) . . ?
F2 C24 C23 120.2(2) . . ?
C25 C24 C23 119.7(3) . . ?
F3 C25 C24 119.9(2) . . ?
F3 C25 C26 120.0(2) . . ?
C24 C25 C26 120.0(2) . . ?
F4 C26 C25 119.4(2) . . ?
F4 C26 C27 120.7(2) . . ?
C25 C26 C27 119.8(2) . . ?
F5 C27 C26 118.2(2) . . ?
F5 C27 C22 119.8(2) . . ?
C26 C27 C22 122.0(2) . . ?
C33 C28 C29 115.7(2) . . ?
C33 C28 C15 122.8(2) . . ?
C29 C28 C15 121.3(2) . . ?
F6 C29 C30 117.3(2) . . ?
F6 C29 C28 120.5(2) . . ?
C30 C29 C28 122.2(3) . . ?
F7 C30 C31 119.8(2) . . ?
F7 C30 C29 119.9(2) . . ?
C31 C30 C29 120.3(2) . . ?
F8 C31 C30 121.1(2) . . ?
F8 C31 C32 119.5(2) . . ?
C30 C31 C32 119.4(2) . . ?
F9 C32 C33 120.9(2) . . ?
F9 C32 C31 119.7(2) . . ?
C33 C32 C31 119.4(2) . . ?
F10 C33 C32 117.6(2) . . ?
F10 C33 C28 119.3(2) . . ?
C32 C33 C28 123.0(2) . . ?
Cl2 C34 Cl1 110.26(16) . . ?
Cl2 C34 Cl3 110.77(16) . . ?
Cl1 C34 Cl3 111.00(16) . . ?
N4 Cu1 N2 172.18(10) . . ?
N4 Cu1 N3 90.18(10) . . ?
N2 Cu1 N3 97.35(9) . . ?
N4 Cu1 N1 81.44(10) . . ?
N2 Cu1 N1 90.91(9) . . ?
N3 Cu1 N1 171.00(9) . . ?
C4 N1 C1 109.7(2) . . ?
C4 N1 Cu1 134.39(19) . . ?
C1 N1 Cu1 115.60(18) . . ?
C6 N2 C9 108.2(2) . . ?
C6 N2 Cu1 128.25(18) . . ?
C9 N2 Cu1 123.51(17) . . ?
C14 N3 C11 107.5(2) . . ?
C14 N3 Cu1 127.69(17) . . ?
C11 N3 Cu1 124.72(17) . . ?
C16 N4 C19 110.1(2) . . ?
C16 N4 Cu1 132.4(2) . . ?
C19 N4 Cu1 115.95(18) . . ?
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 1.383(3) . ?
C1 C19 1.403(4) . ?
C1 C2 1.412(4) . ?
C2 C3 1.376(4) . ?
C3 C4 1.436(4) . ?
C4 N1 1.312(3) . ?
C4 C5 1.503(4) . ?
C5 C6 1.524(4) . ?
C5 C20 1.544(4) . ?
C5 C21 1.557(4) . ?
C6 N2 1.339(3) . ?
C6 C7 1.427(4) . ?
C7 C8 1.356(4) . ?
C8 C9 1.421(4) . ?
C9 N2 1.393(3) . ?
C9 C10 1.396(4) . ?
C10 C11 1.412(3) . ?
C10 C22 1.501(4) . ?
C11 N3 1.371(3) . ?
C11 C12 1.418(4) . ?
C12 C13 1.360(4) . ?
C13 C14 1.424(4) . ?
C14 N3 1.371(3) . ?
C14 C15 1.433(4) . ?
C15 C16 1.379(4) . ?
C15 C28 1.490(4) . ?
C16 N4 1.347(3) . ?
C16 C17 1.457(4) . ?
C17 C18 1.335(4) . ?
C18 C19 1.452(4) . ?
C19 N4 1.351(3) . ?
C22 C23 1.389(4) . ?
C22 C27 1.389(4) . ?
C23 F1 1.341(3) . ?
C23 C24 1.376(4) . ?
C24 F2 1.344(3) . ?
C24 C25 1.364(4) . ?
C25 F3 1.341(3) . ?
C25 C26 1.374(4) . ?
C26 F4 1.347(3) . ?
C26 C27 1.375(4) . ?
C27 F5 1.339(3) . ?
C28 C33 1.382(4) . ?
C28 C29 1.395(4) . ?
C29 F6 1.338(3) . ?
C29 C30 1.376(4) . ?
C30 F7 1.347(3) . ?
C30 C31 1.365(4) . ?
C31 F8 1.329(3) . ?
C31 C32 1.386(4) . ?
C32 F9 1.334(3) . ?
C32 C33 1.374(4) . ?
C33 F10 1.352(3) . ?
C34 Cl2 1.742(3) . ?
C34 Cl1 1.747(3) . ?
C34 Cl3 1.760(3) . ?
Cu1 N4 1.8973(19) . ?
Cu1 N2 1.905(2) . ?
Cu1 N3 1.917(2) . ?
Cu1 N1 1.917(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139156559
