#------------------------------------------------------------------------------
#$Date: 2020-09-22 13:29:47 +0300 (Tue, 22 Sep 2020) $
#$Revision: 256620 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/65/4306537.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_4306537
loop_
_publ_author_name
'Shin Hei Choi'
'Kibong Kim'
'June Jeon'
'Bhupal Meka'
'Daniela Bucella'
'Keliang Pang'
'Snehadrinarayan Khatua'
'Junseong Lee'
'David G. Churchill'
_publ_section_title
;
Optical Effects of S-Oxidation and Mn+ Binding in meso-Thienyl Dipyrrin
Systems and of Stepwise Bromination of
4,4-Difluoro-8-(2,5-dibromo-3-thienyl)-4-bora-3a,4a-diaza-s-indacene
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11071
_journal_page_last               11083
_journal_paper_doi               10.1021/ic801354y
_journal_volume                  47
_journal_year                    2008
_chemical_formula_sum            'C39 H27 Fe N6 S3'
_chemical_formula_weight         731.70
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 113.556(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6785(11)
_cell_length_b                   14.3529(11)
_cell_length_c                   16.9461(12)
_cell_measurement_temperature    273(2)
_cell_volume                     3272.7(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.924
_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  0.0997
_diffrn_reflns_av_sigmaI/netI    0.1389
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22969
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.693
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1508
_refine_diff_density_max         1.544
_refine_diff_density_min         -1.010
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         7524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1766
_refine_ls_R_factor_gt           0.0792
_refine_ls_shift/su_max          6.277
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1205P)²+4.2439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2058
_refine_ls_wR_factor_ref         0.2540
_reflns_number_gt                3751
_reflns_number_total             7524
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801354y_si_008.cif
_cod_data_source_block           dpfes10
_cod_depositor_comments
;

2020-09-22
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C26 H18 Fe0.67 N4 S2'
_cod_original_formula_weight         487.80
_cod_original_formula_units_Z            6
_cod_database_code               4306537
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Fe Fe 0.33876(6) 0.25275(6) 0.49907(5) 0.0236(2) Uani 1 1 d . . .
N1 N 0.2147(3) 0.3167(3) 0.4859(3) 0.0266(11) Uani 1 1 d . . .
N2 N 0.3837(3) 0.3636(3) 0.4563(3) 0.0253(11) Uani 1 1 d . . .
N3 N 0.4071(3) 0.3048(3) 0.6161(3) 0.0269(11) Uani 1 1 d . . .
N4 N 0.4593(3) 0.1826(3) 0.5119(3) 0.0271(11) Uani 1 1 d . . .
N5 N 0.2967(3) 0.1398(3) 0.5413(3) 0.0264(11) Uani 1 1 d . . .
N6 N 0.2676(3) 0.2099(3) 0.3795(3) 0.0277(11) Uani 1 1 d . . .
C11 C 0.1420(4) 0.2804(4) 0.5069(4) 0.0295(14) Uani 1 1 d . . .
H11A H 0.1394 0.2187 0.5225 0.035 Uiso 1 1 calc R . .
C12 C 0.0715(4) 0.3482(5) 0.5021(4) 0.0350(15) Uani 1 1 d . . .
H12A H 0.0148 0.3397 0.5130 0.042 Uiso 1 1 calc R . .
C13 C 0.1021(4) 0.4288(5) 0.4784(4) 0.0333(15) Uani 1 1 d . . .
H13A H 0.0703 0.4861 0.4712 0.040 Uiso 1 1 calc R . .
C14 C 0.1899(4) 0.4108(4) 0.4666(3) 0.0277(13) Uani 1 1 d . . .
C15 C 0.2468(4) 0.4724(4) 0.4410(4) 0.0309(14) Uani 1 1 d . . .
C16 C 0.3347(4) 0.4490(4) 0.4316(3) 0.0285(13) Uani 1 1 d . . .
C17 C 0.3876(4) 0.5041(5) 0.3942(4) 0.0365(15) Uani 1 1 d . . .
H17A H 0.3718 0.5643 0.3727 0.044 Uiso 1 1 calc R . .
C18 C 0.4660(5) 0.4519(5) 0.3957(4) 0.0397(16) Uani 1 1 d . . .
H18A H 0.5129 0.4690 0.3744 0.048 Uiso 1 1 calc R . .
C19 C 0.4620(4) 0.3673(4) 0.4358(4) 0.0316(14) Uani 1 1 d . . .
H19A H 0.5084 0.3197 0.4466 0.038 Uiso 1 1 calc R . .
S1 S 0.27898(15) 0.66054(14) 0.47644(15) 0.0623(6) Uani 1 1 d . . .
C21 C 0.2092(4) 0.5686(4) 0.4222(4) 0.0362(15) Uani 1 1 d . . .
C22 C 0.1126(4) 0.6004(4) 0.3655(4) 0.0351(15) Uani 1 1 d . . .
H22A H 0.0626 0.5623 0.3283 0.042 Uiso 1 1 calc R . .
C23 C 0.1041(6) 0.6946(6) 0.3735(6) 0.066(2) Uani 1 1 d . . .
H23A H 0.0463 0.7273 0.3417 0.079 Uiso 1 1 calc R . .
C24 C 0.1856(6) 0.7363(5) 0.4310(7) 0.067(3) Uani 1 1 d . . .
H24A H 0.1897 0.7995 0.4440 0.081 Uiso 1 1 calc R . .
C31 C 0.3704(5) 0.3663(4) 0.6533(4) 0.0335(14) Uani 1 1 d . . .
H31A H 0.3067 0.3911 0.6278 0.040 Uiso 1 1 calc R . .
C32 C 0.4393(5) 0.3898(5) 0.7359(4) 0.0389(16) Uani 1 1 d . . .
H32A H 0.4301 0.4319 0.7738 0.047 Uiso 1 1 calc R . .
C33 C 0.5221(5) 0.3388(5) 0.7496(4) 0.0393(16) Uani 1 1 d . . .
H33A H 0.5802 0.3390 0.7995 0.047 Uiso 1 1 calc R . .
C34 C 0.5051(4) 0.2857(4) 0.6757(4) 0.0305(14) Uani 1 1 d . . .
C35 C 0.5688(4) 0.2255(4) 0.6603(4) 0.0293(14) Uani 1 1 d . . .
C36 C 0.5498(4) 0.1763(4) 0.5838(4) 0.0314(14) Uani 1 1 d . . .
C37 C 0.6127(4) 0.1160(5) 0.5624(4) 0.0374(16) Uani 1 1 d . . .
H37A H 0.6770 0.0993 0.5987 0.045 Uiso 1 1 calc R . .
C38 C 0.5638(5) 0.0869(5) 0.4806(4) 0.0414(17) Uani 1 1 d . . .
H38A H 0.5876 0.0475 0.4496 0.050 Uiso 1 1 calc R . .
C39 C 0.4694(5) 0.1284(5) 0.4522(4) 0.0374(16) Uani 1 1 d . . .
H39A H 0.4196 0.1190 0.3977 0.045 Uiso 1 1 calc R . .
S2 S 0.6965(2) 0.1134(3) 0.7878(2) 0.1287(14) Uani 1 1 d . . .
C41 C 0.6691(4) 0.2118(5) 0.7311(4) 0.0345(15) Uani 1 1 d . . .
C42 C 0.7557(3) 0.2895(4) 0.7609(3) 0.0191(12) Uani 1 1 d . . .
H42A H 0.7576 0.3496 0.7412 0.023 Uiso 1 1 calc R . .
C43 C 0.8344(5) 0.2313(6) 0.8327(5) 0.058(2) Uani 1 1 d . . .
H43A H 0.8981 0.2544 0.8630 0.070 Uiso 1 1 calc R . .
C44 C 0.8090(5) 0.1485(7) 0.8499(5) 0.064(2) Uani 1 1 d . . .
H44A H 0.8521 0.1120 0.8945 0.077 Uiso 1 1 calc R . .
C51 C 0.3294(5) 0.1143(4) 0.6243(4) 0.0339(15) Uani 1 1 d . . .
H51A H 0.3769 0.1465 0.6698 0.041 Uiso 1 1 calc R . .
C52 C 0.2819(5) 0.0317(5) 0.6329(4) 0.0393(16) Uani 1 1 d . . .
H52A H 0.2926 0.0006 0.6840 0.047 Uiso 1 1 calc R . .
C53 C 0.2170(5) 0.0060(5) 0.5518(4) 0.0366(15) Uani 1 1 d . . .
H53A H 0.1753 -0.0457 0.5375 0.044 Uiso 1 1 calc R . .
C54 C 0.2261(4) 0.0743(4) 0.4938(4) 0.0280(13) Uani 1 1 d . . .
C55 C 0.1782(4) 0.0754(4) 0.4040(4) 0.0282(13) Uani 1 1 d . . .
C56 C 0.1987(4) 0.1368(4) 0.3505(3) 0.0281(13) Uani 1 1 d . . .
C57 C 0.1558(4) 0.1404(5) 0.2582(4) 0.0362(15) Uani 1 1 d . . .
H57A H 0.1071 0.1006 0.2218 0.043 Uiso 1 1 calc R . .
C58 C 0.1984(5) 0.2111(5) 0.2337(4) 0.0408(16) Uani 1 1 d . . .
H58A H 0.1853 0.2283 0.1773 0.049 Uiso 1 1 calc R . .
C59 C 0.2663(4) 0.2545(5) 0.3084(3) 0.0332(14) Uani 1 1 d . . .
H59A H 0.3047 0.3062 0.3090 0.040 Uiso 1 1 calc R . .
S3 S -0.00690(15) 0.01066(16) 0.38539(14) 0.0618(6) Uani 1 1 d . . .
C61 C 0.0978(5) 0.0081(4) 0.3626(4) 0.0343(14) Uani 1 1 d . . .
C62 C 0.0866(5) -0.0574(4) 0.2966(4) 0.0420(17) Uani 1 1 d . . .
H62A H 0.1333 -0.0692 0.2735 0.050 Uiso 1 1 calc R . .
C63 C -0.0078(6) -0.1024(5) 0.2712(5) 0.053(2) Uani 1 1 d . . .
H63A H -0.0282 -0.1492 0.2298 0.064 Uiso 1 1 calc R . .
C64 C -0.0645(6) -0.0729(6) 0.3106(5) 0.063(2) Uani 1 1 d . . .
H64A H -0.1281 -0.0952 0.2988 0.075 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 '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
N5 Fe N2 178.4(2) . . ?
N5 Fe N6 90.15(19) . . ?
N2 Fe N6 89.53(19) . . ?
N5 Fe N1 90.87(19) . . ?
N2 Fe N1 90.72(19) . . ?
N6 Fe N1 86.71(19) . . ?
N5 Fe N4 86.4(2) . . ?
N2 Fe N4 92.01(19) . . ?
N6 Fe N4 92.14(19) . . ?
N1 Fe N4 177.0(2) . . ?
N5 Fe N3 93.04(19) . . ?
N2 Fe N3 87.35(19) . . ?
N6 Fe N3 176.0(2) . . ?
N1 Fe N3 90.76(19) . . ?
N4 Fe N3 90.53(19) . . ?
C11 N1 C14 105.8(5) . . ?
C11 N1 Fe 125.4(4) . . ?
C14 N1 Fe 128.1(4) . . ?
C19 N2 C16 106.4(5) . . ?
C19 N2 Fe 125.5(4) . . ?
C16 N2 Fe 127.6(4) . . ?
C31 N3 C34 106.4(5) . . ?
C31 N3 Fe 126.3(4) . . ?
C34 N3 Fe 127.3(4) . . ?
C39 N4 C36 105.6(5) . . ?
C39 N4 Fe 125.7(4) . . ?
C36 N4 Fe 128.7(4) . . ?
C51 N5 C54 107.1(5) . . ?
C51 N5 Fe 125.0(4) . . ?
C54 N5 Fe 127.9(4) . . ?
C59 N6 C56 106.8(5) . . ?
C59 N6 Fe 125.4(4) . . ?
C56 N6 Fe 127.3(4) . . ?
N1 C11 C12 111.1(5) . . ?
C13 C12 C11 106.5(5) . . ?
C12 C13 C14 108.4(5) . . ?
C15 C14 N1 123.3(5) . . ?
C15 C14 C13 128.6(6) . . ?
N1 C14 C13 108.1(5) . . ?
C14 C15 C16 125.0(6) . . ?
C14 C15 C21 116.1(5) . . ?
C16 C15 C21 118.8(5) . . ?
N2 C16 C15 124.3(5) . . ?
N2 C16 C17 108.2(5) . . ?
C15 C16 C17 127.5(6) . . ?
C18 C17 C16 107.0(6) . . ?
C17 C18 C19 106.6(6) . . ?
N2 C19 C18 111.6(6) . . ?
C24 S1 C21 92.8(4) . . ?
C22 C21 C15 128.9(6) . . ?
C22 C21 S1 109.7(5) . . ?
C15 C21 S1 121.2(5) . . ?
C23 C22 C21 110.6(6) . . ?
C24 C23 C22 114.9(7) . . ?
C23 C24 S1 111.9(6) . . ?
N3 C31 C32 111.6(6) . . ?
C33 C32 C31 106.3(6) . . ?
C32 C33 C34 108.3(5) . . ?
C35 C34 C33 128.4(6) . . ?
C35 C34 N3 124.2(5) . . ?
C33 C34 N3 107.4(5) . . ?
C34 C35 C36 126.4(5) . . ?
C34 C35 C41 117.2(5) . . ?
C36 C35 C41 116.4(5) . . ?
N4 C36 C35 122.8(5) . . ?
N4 C36 C37 107.7(5) . . ?
C35 C36 C37 129.5(5) . . ?
C38 C37 C36 108.7(5) . . ?
C37 C38 C39 105.5(6) . . ?
N4 C39 C38 112.4(5) . . ?
C44 S2 C41 93.4(4) . . ?
C35 C41 C42 124.1(5) . . ?
C35 C41 S2 120.6(5) . . ?
C42 C41 S2 115.3(4) . . ?
C43 C42 C41 96.9(5) . . ?
C44 C43 C42 118.4(6) . . ?
C43 C44 S2 115.9(6) . . ?
N5 C51 C52 110.6(6) . . ?
C53 C52 C51 107.3(5) . . ?
C52 C53 C54 106.6(6) . . ?
N5 C54 C55 123.7(5) . . ?
N5 C54 C53 108.5(5) . . ?
C55 C54 C53 127.7(6) . . ?
C56 C55 C54 125.2(5) . . ?
C56 C55 C61 116.8(5) . . ?
C54 C55 C61 118.0(6) . . ?
C55 C56 N6 124.2(5) . . ?
C55 C56 C57 128.5(6) . . ?
N6 C56 C57 107.3(5) . . ?
C58 C57 C56 108.0(6) . . ?
C57 C58 C59 107.9(5) . . ?
N6 C59 C58 110.1(6) . . ?
C64 S3 C61 92.3(4) . . ?
C62 C61 C55 129.0(6) . . ?
C62 C61 S3 110.9(5) . . ?
C55 C61 S3 119.8(4) . . ?
C61 C62 C63 109.2(7) . . ?
C64 C63 C62 115.6(7) . . ?
C63 C64 S3 112.0(6) . . ?
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
Fe N5 1.968(5) . ?
Fe N2 1.969(5) . ?
Fe N6 1.970(4) . ?
Fe N1 1.970(5) . ?
Fe N4 1.972(5) . ?
Fe N3 1.977(4) . ?
N1 C11 1.356(7) . ?
N1 C14 1.404(7) . ?
N2 C19 1.327(7) . ?
N2 C16 1.398(7) . ?
N3 C31 1.318(7) . ?
N3 C34 1.415(7) . ?
N4 C39 1.331(7) . ?
N4 C36 1.401(7) . ?
N5 C51 1.342(7) . ?
N5 C54 1.393(7) . ?
N6 C59 1.358(7) . ?
N6 C56 1.403(7) . ?
C11 C12 1.399(8) . ?
C12 C13 1.359(9) . ?
C13 C14 1.405(8) . ?
C14 C15 1.399(8) . ?
C15 C16 1.402(8) . ?
C15 C21 1.474(8) . ?
C16 C17 1.423(8) . ?
C17 C18 1.364(9) . ?
C18 C19 1.404(9) . ?
S1 C24 1.676(8) . ?
S1 C21 1.697(7) . ?
C21 C22 1.433(8) . ?
C22 C23 1.370(10) . ?
C23 C24 1.344(11) . ?
C31 C32 1.403(8) . ?
C32 C33 1.357(9) . ?
C33 C34 1.401(8) . ?
C34 C35 1.373(9) . ?
C35 C36 1.402(8) . ?
C35 C41 1.495(7) . ?
C36 C37 1.414(8) . ?
C37 C38 1.347(9) . ?
C38 C39 1.405(8) . ?
S2 C44 1.643(8) . ?
S2 C41 1.664(7) . ?
C41 C42 1.613(8) . ?
C42 C43 1.546(8) . ?
C43 C44 1.312(11) . ?
C51 C52 1.412(9) . ?
C52 C53 1.373(9) . ?
C53 C54 1.433(8) . ?
C54 C55 1.398(8) . ?
C55 C56 1.380(8) . ?
C55 C61 1.469(8) . ?
C56 C57 1.433(8) . ?
C57 C58 1.342(9) . ?
C58 C59 1.406(8) . ?
S3 C64 1.704(8) . ?
S3 C61 1.728(7) . ?
C61 C62 1.421(9) . ?
C62 C63 1.431(10) . ?
C63 C64 1.327(11) . ?
