#------------------------------------------------------------------------------
#$Date: 2018-08-09 02:09:34 +0300 (Thu, 09 Aug 2018) $
#$Revision: 209492 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/72/7047233.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_7047233
loop_
_publ_author_name
'Wiehe, Arno'
'Gutsche, Claudia Simone'
'Gräfe, Susanna'
'Gitter, Burkhard'
'Flanagan, Keith'
'Senge, Mathias'
'Kulak, Nora'
_publ_section_title
;
 Pre-/Post-functionalization in Dipyrrin Metal Complexes -- Antitumor and
 Antibacterial Activity of their Glycosylated Derivatives
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/C8DT03059F
_journal_year                    2018
_chemical_formula_moiety         'C57 H45 F12 Fe1 N6 O3'
_chemical_formula_sum            'C57 H45 F12 Fe N6 O3'
_chemical_formula_weight         1145.84
_chemical_name_systematic
{Tris[5-(4-butyloxytetrafluorophenyl)dipyrrin]}-iron(III)
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-04-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-05-02 deposited with the CCDC.
2018-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   24.0020(11)
_cell_length_b                   24.0020(11)
_cell_length_c                   15.1852(9)
_cell_measurement_reflns_used    6014
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.05
_cell_measurement_theta_min      3.60
_cell_volume                     7576.1(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX 3 (Bruker, 2016) '
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1428
_diffrn_reflns_av_unetI/netI     0.0980
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31292
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.200
_diffrn_reflns_theta_min         3.605
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.253
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.2921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1629 before and 0.1117 after correction. The Ratio of minimum to maximum transmission is 0.3878. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             3522
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and methanol by slow evaporation'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0605
_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)+(0.0743P)²+14.2689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.1686
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2541
_reflns_number_total             3129
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt03059f2.cif
_cod_data_source_block           kjf115
_cod_original_cell_volume        7576.1(8)
_cod_database_code               7047233
_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_max   0.938
_shelx_estimated_absorpt_t_min   0.246
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN micromount using oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
_atom_site_refinement_flags_occupancy
C1 C 0.37854(15) 0.54019(15) 0.2807(2) 0.0226(6) Uani 1 1 d . . .
H1 H 0.3757 0.4999 0.2700 0.027 Uiso 1 1 calc R . .
C2 C 0.41516(15) 0.59607(15) 0.2351(2) 0.0234(6) Uani 1 1 d . . .
H2 H 0.4425 0.6018 0.1865 0.028 Uiso 1 1 calc R . .
C3 C 0.40469(15) 0.64347(16) 0.27376(19) 0.0231(6) Uani 1 1 d . . .
H3 H 0.4248 0.6870 0.2550 0.028 Uiso 1 1 calc R . .
C5 C 0.24196(15) 0.58584(15) 0.5536(2) 0.0232(7) Uani 1 1 d . . .
H5 H 0.2390 0.6211 0.5764 0.028 Uiso 1 1 calc R . .
C6 C 0.20674(16) 0.52249(16) 0.5855(2) 0.0255(7) Uani 1 1 d . . .
H6 H 0.1768 0.5079 0.6327 0.031 Uiso 1 1 calc R . .
C7 C 0.22374(15) 0.48572(15) 0.53539(19) 0.0233(7) Uani 1 1 d . . .
H7 H 0.2075 0.4408 0.5410 0.028 Uiso 1 1 calc R . .
C8 C 0.30186(14) 0.51209(14) 0.40989(19) 0.0189(6) Uani 1 1 d . . .
C9 C 0.34538(14) 0.55409(14) 0.34751(19) 0.0195(6) Uani 1 1 d . . .
C10 C 0.27042(15) 0.52785(14) 0.47327(19) 0.0199(6) Uani 1 1 d . . .
C11 C 0.28870(15) 0.44424(14) 0.4078(2) 0.0212(6) Uani 1 1 d . . .
C12 C 0.30879(16) 0.41969(16) 0.4752(2) 0.0255(7) Uani 1 1 d . . .
C13 C 0.29633(17) 0.35650(17) 0.4740(2) 0.0295(7) Uani 1 1 d . . .
C14 C 0.26336(17) 0.31497(16) 0.4048(2) 0.0289(7) Uani 1 1 d . . .
C15 C 0.24331(16) 0.33970(15) 0.3369(2) 0.0256(7) Uani 1 1 d . . .
C16 C 0.25615(15) 0.40276(14) 0.33877(19) 0.0219(6) Uani 1 1 d . . .
C17 C 0.2604(2) 0.22350(17) 0.3346(2) 0.0357(8) Uani 1 1 d . . .
H17A H 0.2772 0.2546 0.2853 0.043 Uiso 1 1 calc R . .
H17B H 0.2191 0.1860 0.3159 0.043 Uiso 1 1 calc R . .
C18 C 0.30748(17) 0.20216(18) 0.3572(2) 0.0328(8) Uani 1 1 d . . .
H18A H 0.2919 0.1734 0.4092 0.039 Uiso 1 1 calc R . .
H18B H 0.3494 0.2401 0.3726 0.039 Uiso 1 1 calc R . .
C19 C 0.31632(17) 0.16679(17) 0.2801(2) 0.0317(8) Uani 1 1 d . . .
H19A H 0.2736 0.1319 0.2608 0.038 Uiso 1 1 calc R . .
H19B H 0.3358 0.1971 0.2303 0.038 Uiso 1 1 calc R . .
C20 C 0.3583(2) 0.1380(2) 0.3018(3) 0.0506(11) Uani 1 1 d . . .
H20A H 0.3614 0.1152 0.2502 0.076 Uiso 1 1 calc GR . .
H20B H 0.3393 0.1078 0.3510 0.076 Uiso 1 1 calc GR . .
H20C H 0.4014 0.1725 0.3184 0.076 Uiso 1 1 calc GR . .
F1 F 0.34272(10) 0.45676(10) 0.54298(12) 0.0332(5) Uani 1 1 d . . .
F2 F 0.31744(12) 0.33547(11) 0.54127(14) 0.0426(6) Uani 1 1 d . . .
F3 F 0.20952(10) 0.30226(9) 0.26902(13) 0.0336(5) Uani 1 1 d . . .
F4 F 0.23274(9) 0.42205(9) 0.27264(12) 0.0266(4) Uani 1 1 d . . .
Fe1 Fe 0.3333 0.6667 0.41433(5) 0.0172(2) Uani 1 3 d S T P
N1 N 0.36259(12) 0.61881(12) 0.34060(16) 0.0201(5) Uani 1 1 d . . .
N2 N 0.28048(12) 0.58986(12) 0.48677(16) 0.0207(5) Uani 1 1 d . . .
O1 O 0.25003(15) 0.25353(12) 0.41165(17) 0.0455(8) 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 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 C1 H1 126.6 . .
C2 C1 C9 106.9(3) . .
C9 C1 H1 126.6 . .
C1 C2 H2 126.5 . .
C1 C2 C3 107.1(3) . .
C3 C2 H2 126.5 . .
C2 C3 H3 124.5 . .
N1 C3 C2 111.0(3) . .
N1 C3 H3 124.5 . .
C6 C5 H5 124.5 . .
N2 C5 H5 124.5 . .
N2 C5 C6 110.9(3) . .
C5 C6 H6 126.5 . .
C7 C6 C5 107.1(3) . .
C7 C6 H6 126.5 . .
C6 C7 H7 126.5 . .
C6 C7 C10 106.9(3) . .
C10 C7 H7 126.5 . .
C9 C8 C11 116.5(3) . .
C10 C8 C9 125.9(3) . .
C10 C8 C11 117.6(3) . .
C8 C9 C1 128.0(3) . .
C8 C9 N1 123.5(3) . .
N1 C9 C1 108.5(3) . .
C8 C10 C7 127.4(3) . .
C8 C10 N2 124.3(3) . .
N2 C10 C7 108.3(3) . .
C12 C11 C8 121.3(3) . .
C12 C11 C16 116.4(3) . .
C16 C11 C8 122.3(3) . .
C11 C12 C13 121.6(3) . .
F1 C12 C11 120.8(3) . .
F1 C12 C13 117.5(3) . .
C14 C13 C12 121.7(3) . .
F2 C13 C12 118.9(3) . .
F2 C13 C14 119.4(3) . .
C15 C14 C13 116.7(3) . .
O1 C14 C13 117.7(3) . .
O1 C14 C15 125.5(3) . .
C16 C15 C14 121.0(3) . .
F3 C15 C14 120.4(3) . .
F3 C15 C16 118.5(3) . .
C15 C16 C11 122.5(3) . .
F4 C16 C11 120.1(3) . .
F4 C16 C15 117.3(3) . .
H17A C17 H17B 108.3 . .
C18 C17 H17A 109.8 . .
C18 C17 H17B 109.8 . .
O1 C17 H17A 109.8 . .
O1 C17 H17B 109.8 . .
O1 C17 C18 109.3(3) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
C17 C18 C19 110.8(3) . .
H18A C18 H18B 108.1 . .
C19 C18 H18A 109.5 . .
C19 C18 H18B 109.5 . .
C18 C19 H19A 108.9 . .
C18 C19 H19B 108.9 . .
H19A C19 H19B 107.7 . .
C20 C19 C18 113.3(3) . .
C20 C19 H19A 108.9 . .
C20 C19 H19B 108.9 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
N1 Fe1 N1 90.82(10) 3_565 2_665
N1 Fe1 N1 90.83(10) 2_665 .
N1 Fe1 N1 90.83(10) 3_565 .
N1 Fe1 N2 86.17(10) 2_665 3_565
N1 Fe1 N2 86.17(10) . 2_665
N1 Fe1 N2 176.36(10) . 3_565
N1 Fe1 N2 91.27(10) . .
N1 Fe1 N2 91.27(10) 3_565 3_565
N1 Fe1 N2 91.27(10) 2_665 2_665
N1 Fe1 N2 176.36(10) 2_665 .
N1 Fe1 N2 176.36(10) 3_565 2_665
N1 Fe1 N2 86.17(10) 3_565 .
N2 Fe1 N2 91.84(10) 3_565 2_665
N2 Fe1 N2 91.84(10) . 2_665
N2 Fe1 N2 91.84(10) 3_565 .
C3 N1 C9 106.6(3) . .
C3 N1 Fe1 125.6(2) . .
C9 N1 Fe1 127.8(2) . .
C5 N2 C10 106.7(3) . .
C5 N2 Fe1 126.0(2) . .
C10 N2 Fe1 127.0(2) . .
C14 O1 C17 118.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.9500 .
C1 C2 1.369(4) .
C1 C9 1.428(4) .
C2 H2 0.9500 .
C2 C3 1.410(4) .
C3 H3 0.9500 .
C3 N1 1.343(4) .
C5 H5 0.9500 .
C5 C6 1.405(5) .
C5 N2 1.344(4) .
C6 H6 0.9500 .
C6 C7 1.372(4) .
C7 H7 0.9500 .
C7 C10 1.427(4) .
C8 C9 1.397(4) .
C8 C10 1.387(4) .
C8 C11 1.496(4) .
C9 N1 1.398(4) .
C10 N2 1.399(4) .
C11 C12 1.382(4) .
C11 C16 1.386(4) .
C12 C13 1.392(5) .
C12 F1 1.338(4) .
C13 C14 1.391(5) .
C13 F2 1.346(4) .
C14 C15 1.390(5) .
C14 O1 1.348(4) .
C15 C16 1.386(4) .
C15 F3 1.341(4) .
C16 F4 1.341(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C18 1.496(5) .
C17 O1 1.458(4) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C18 C19 1.523(5) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C19 C20 1.516(5) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
Fe1 N1 1.968(3) 3_565
Fe1 N1 1.968(3) 2_665
Fe1 N1 1.968(3) .
Fe1 N2 1.970(3) 3_565
Fe1 N2 1.970(3) .
Fe1 N2 1.970(3) 2_665
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 F4 0.95 2.41 3.292(3) 154.3 15
C17 H17A F2 0.99 2.38 3.315(4) 157.2 9_554
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
C1 C2 C3 N1 -0.7(4)
C1 C9 N1 C3 -0.7(3)
C1 C9 N1 Fe1 -179.6(2)
C2 C1 C9 C8 179.3(3)
C2 C1 C9 N1 0.3(3)
C2 C3 N1 C9 0.9(3)
C2 C3 N1 Fe1 179.8(2)
C5 C6 C7 C10 0.7(4)
C6 C5 N2 C10 0.4(4)
C6 C5 N2 Fe1 174.4(2)
C6 C7 C10 C8 179.1(3)
C6 C7 C10 N2 -0.4(3)
C7 C10 N2 C5 0.0(3)
C7 C10 N2 Fe1 -173.9(2)
C8 C9 N1 C3 -179.7(3)
C8 C9 N1 Fe1 1.3(4)
C8 C10 N2 C5 -179.6(3)
C8 C10 N2 Fe1 6.5(4)
C8 C11 C12 C13 179.5(3)
C8 C11 C12 F1 -2.4(5)
C8 C11 C16 C15 -179.4(3)
C8 C11 C16 F4 -2.9(5)
C9 C1 C2 C3 0.3(3)
C9 C8 C10 C7 177.1(3)
C9 C8 C10 N2 -3.4(5)
C9 C8 C11 C12 111.8(3)
C9 C8 C11 C16 -68.0(4)
C10 C8 C9 C1 -179.5(3)
C10 C8 C9 N1 -0.7(5)
C10 C8 C11 C12 -67.9(4)
C10 C8 C11 C16 112.3(3)
C11 C8 C9 C1 0.9(4)
C11 C8 C9 N1 179.7(3)
C11 C8 C10 C7 -3.3(5)
C11 C8 C10 N2 176.2(3)
C11 C12 C13 C14 0.3(5)
C11 C12 C13 F2 179.6(3)
C12 C11 C16 C15 0.8(5)
C12 C11 C16 F4 177.2(3)
C12 C13 C14 C15 -0.2(5)
C12 C13 C14 O1 -176.1(3)
C13 C14 C15 C16 0.3(5)
C13 C14 C15 F3 -178.0(3)
C13 C14 O1 C17 -136.3(4)
C14 C15 C16 C11 -0.6(5)
C14 C15 C16 F4 -177.2(3)
C15 C14 O1 C17 48.2(5)
C16 C11 C12 C13 -0.6(5)
C16 C11 C12 F1 177.4(3)
C17 C18 C19 C20 -174.2(3)
C18 C17 O1 C14 121.1(4)
F1 C12 C13 C14 -177.8(3)
F1 C12 C13 F2 1.5(5)
F2 C13 C14 C15 -179.4(3)
F2 C13 C14 O1 4.7(5)
F3 C15 C16 C11 177.6(3)
F3 C15 C16 F4 1.1(4)
N2 C5 C6 C7 -0.7(4)
O1 C14 C15 C16 175.8(3)
O1 C14 C15 F3 -2.4(5)
O1 C17 C18 C19 176.5(3)
