#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:06:29 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179362 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/59/4325992.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_4325992
loop_
_publ_author_name
'Dongmei Li'
'Xiaohe Tian'
'Guiju Hu'
'Qiong Zhang'
'Peng Wang'
'Pingping Sun'
'Hongping Zhou'
'Xiangming Meng'
'Jiaxiang Yang'
'Jieying Wu'
'Baokang Jin'
'Shengyi Zhang'
'Xutang Tao'
'Yupeng Tian'
_publ_section_title
;
 Synthesis, Crystal Structures, Photophysical Properties, and Bioimaging
 of Living Cells of Bis-β-Diketonate Phenothiazine Ligands and Its Cyclic
 Dinuclear Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7997
_journal_page_last               8006
_journal_paper_doi               10.1021/ic200150h
_journal_volume                  50
_journal_year                    2011
_chemical_formula_sum            'C64 H46 F12 Mn2 N6 O8 S2'
_chemical_formula_weight         1429.07
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.086(8)
_cell_angle_beta                 96.614(9)
_cell_angle_gamma                111.179(8)
_cell_formula_units_Z            1
_cell_length_a                   8.544(6)
_cell_length_b                   9.937(7)
_cell_length_c                   19.474(13)
_cell_measurement_temperature    298(2)
_cell_volume                     1528.2(18)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0800
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7776
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      0
_exptl_crystal_F_000             726
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.207
_refine_diff_density_min         -1.328
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1820
_refine_ls_R_factor_gt           0.1472
_refine_ls_shift/su_max          0.249
_refine_ls_shift/su_mean         0.036
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.5160P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4934
_refine_ls_wR_factor_ref         0.5416
_reflns_number_gt                3446
_reflns_number_total             5231
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic200150h_si_007.cif
_cod_data_source_block           071116c
_cod_original_cell_volume        1528.2(17)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4325992
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Mn1 Mn 0.2321(2) 0.49557(17) 0.19244(8) 0.0485(7) Uani 1 1 d .
C1 C 0.232(3) 0.0916(17) 0.0987(8) 0.090(6) Uani 1 1 d .
C2 C 0.1922(17) 0.1887(13) 0.1493(6) 0.055(3) Uani 1 1 d .
C3 C 0.1131(14) 0.1268(12) 0.2043(5) 0.044(2) Uani 1 1 d .
H3 H 0.0863 0.0280 0.2078 0.053 Uiso 1 1 calc R
C4 C 0.0701(13) 0.2031(11) 0.2556(5) 0.043(2) Uani 1 1 d .
C5 C -0.0207(13) 0.1269(11) 0.3130(5) 0.040(2) Uani 1 1 d .
C6 C -0.0766(15) -0.0203(12) 0.3168(6) 0.049(3) Uani 1 1 d .
H6 H -0.0564 -0.0761 0.2825 0.059 Uiso 1 1 calc R
C7 C -0.1648(16) -0.0904(12) 0.3720(6) 0.052(3) Uani 1 1 d .
H7 H -0.1991 -0.1902 0.3740 0.063 Uiso 1 1 calc R
C8 C -0.1986(13) -0.0089(12) 0.4219(6) 0.045(2) Uani 1 1 d .
C9 C -0.1391(11) 0.1424(11) 0.4191(5) 0.035(2) Uani 1 1 d .
C10 C -0.0521(13) 0.2027(12) 0.3661(5) 0.043(2) Uani 1 1 d .
H10 H -0.0106 0.3030 0.3658 0.052 Uiso 1 1 calc R
C11 C -0.2972(12) -0.0062(11) 0.5353(5) 0.040(2) Uani 1 1 d .
C12 C -0.2374(12) 0.1466(10) 0.5469(5) 0.037(2) Uani 1 1 d .
C13 C -0.2405(13) 0.2125(12) 0.6070(5) 0.046(2) Uani 1 1 d .
H13 H -0.1935 0.3129 0.6125 0.055 Uiso 1 1 calc R
C14 C -0.3138(13) 0.1332(12) 0.6625(6) 0.043(2) Uani 1 1 d .
C15 C -0.3706(15) -0.0153(11) 0.6524(6) 0.050(3) Uani 1 1 d .
H15 H -0.4171 -0.0717 0.6878 0.060 Uiso 1 1 calc R
C16 C -0.3609(14) -0.0818(12) 0.5927(6) 0.049(3) Uani 1 1 d .
H16 H -0.3981 -0.1823 0.5893 0.059 Uiso 1 1 calc R
C17 C 0.6101(17) 0.8918(15) 0.1329(8) 0.069(4) Uani 1 1 d .
C18 C 0.4690(14) 0.8009(13) 0.1717(5) 0.050(3) Uani 1 1 d .
C19 C 0.4433(14) 0.8586(13) 0.2319(5) 0.051(3) Uani 1 1 d .
H19 H 0.5118 0.9542 0.2451 0.061 Uiso 1 1 calc R
C20 C 0.3261(13) 0.7891(11) 0.2747(5) 0.041(2) Uani 1 1 d .
C21 C -0.016(2) 0.6092(16) 0.0985(9) 0.076(4) Uani 1 1 d .
H21 H 0.0586 0.6998 0.1167 0.091 Uiso 1 1 calc R
C22 C -0.1213(19) 0.3547(16) 0.0978(9) 0.079(4) Uani 1 1 d .
H22 H -0.1128 0.2716 0.1162 0.095 Uiso 1 1 calc R
C23 C -0.245(3) 0.342(3) 0.0520(9) 0.109(7) Uani 1 1 d .
H23 H -0.3247 0.2510 0.0383 0.131 Uiso 1 1 calc R
C24 C -0.264(2) 0.467(3) 0.0206(10) 0.116(8) Uani 1 1 d .
H24 H -0.3487 0.4620 -0.0150 0.139 Uiso 1 1 calc R
C25 C -0.142(2) 0.595(2) 0.0497(10) 0.087(5) Uani 1 1 d .
H25 H -0.1490 0.6798 0.0330 0.104 Uiso 1 1 calc R
N2 N 0.4886(3) 0.5122(4) 0.27466(15) 0.23(2) Uani 1 1 d G
C26 C 0.5285(3) 0.4396(4) 0.33026(18) 0.161(12) Uani 1 1 d G
H26 H 0.4546 0.4082 0.3632 0.194 Uiso 1 1 calc R
C27 C 0.6787(3) 0.4137(5) 0.3366(2) 0.168(14) Uani 1 1 d G
H27 H 0.7054 0.3651 0.3738 0.202 Uiso 1 1 calc R
C28 C 0.7891(4) 0.4606(6) 0.2874(2) 1.3(2) Uani 1 1 d G
H28 H 0.8896 0.4433 0.2917 1.615 Uiso 1 1 calc R
C29 C 0.7492(4) 0.5332(5) 0.2318(2) 0.49(8) Uani 1 1 d G
H29 H 0.8231 0.5646 0.1989 0.583 Uiso 1 1 calc R
C33 C 0.5990(3) 0.5591(4) 0.22546(18) 0.45(6) Uani 1 1 d G
H33 H 0.5723 0.6077 0.1883 0.542 Uiso 1 1 calc R
C30 C -0.3854(5) -0.2339(2) 0.46573(17) 0.047(3) Uani 1 1 d G
H30A H -0.4235 -0.2614 0.4169 0.057 Uiso 1 1 calc R
H30B H -0.4854 -0.2578 0.4891 0.057 Uiso 1 1 calc R
C31 C -0.2875(6) -0.3234(3) 0.4925(2) 0.061(3) Uani 1 1 d G
H31A H -0.1845 -0.2973 0.4720 0.091 Uiso 1 1 calc R
H31B H -0.3539 -0.4239 0.4809 0.091 Uiso 1 1 calc R
H31C H -0.2611 -0.3069 0.5420 0.091 Uiso 1 1 calc R
F1 F 0.6853(5) 1.0260(3) 0.1570(2) 0.090(3) Uani 1 1 d G
F2 F 0.5471(5) 0.8956(4) 0.06668(17) 0.094(3) Uani 1 1 d G
F3 F 0.1978(7) 0.1136(4) 0.03757(18) 0.192(10) Uani 1 1 d G
F4 F 0.1743(8) -0.0426(3) 0.1065(2) 0.146(6) Uani 1 1 d G
F5 F 0.3971(7) 0.1277(4) 0.1026(2) 0.198(10) Uani 1 1 d G
F6 F 0.7264(4) 0.8395(4) 0.13074(19) 0.124(5) Uani 1 1 d G
N1 N -0.0009(4) 0.4854(4) 0.12099(11) 0.052(2) Uani 1 1 d G
N3 N -0.2956(4) -0.0760(2) 0.47364(14) 0.046(2) Uani 1 1 d G
O1 O 0.2429(5) 0.3194(3) 0.13510(14) 0.063(2) Uani 1 1 d G
O2 O 0.1001(3) 0.3356(2) 0.25706(10) 0.055(2) Uani 1 1 d G
O3 O 0.2292(3) 0.6574(2) 0.26478(13) 0.054(2) Uani 1 1 d G
O4 O 0.3939(4) 0.6730(3) 0.14369(14) 0.056(2) Uani 1 1 d G
S1 S -0.1810(3) 0.2567(2) 0.47652(11) 0.0473(9) Uani 1 1 d G
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 '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_3
O1 Mn1 O2 84.02(11) .
O1 Mn1 O3 170.87(15) .
O2 Mn1 O3 89.02(10) .
O1 Mn1 O4 101.52(11) .
O2 Mn1 O4 169.95(17) .
O3 Mn1 O4 84.53(11) .
O1 Mn1 N1 89.97(12) .
O2 Mn1 N1 95.52(12) .
O3 Mn1 N1 96.60(12) .
O4 Mn1 N1 92.88(11) .
O1 Mn1 N2 91.90(12) .
O2 Mn1 N2 84.17(11) .
O3 Mn1 N2 81.48(10) .
O4 Mn1 N2 87.25(11) .
N1 Mn1 N2 178.06(13) .
F3 C1 F4 109.6(15) .
F3 C1 F5 100.3(10) .
F4 C1 F5 105.1(12) .
F3 C1 C2 113.1(12) .
F4 C1 C2 117.5(10) .
F5 C1 C2 109.6(15) .
O1 C2 C3 128.7(10) .
O1 C2 C1 113.7(10) .
C3 C2 C1 117.6(11) .
C2 C3 C4 124.1(11) .
C2 C3 H3 118.0 .
C4 C3 H3 117.9 .
O2 C4 C3 124.2(9) .
O2 C4 C5 114.9(9) .
C3 C4 C5 120.9(10) .
C6 C5 C10 115.9(9) .
C6 C5 C4 123.1(9) .
C10 C5 C4 121.0(9) .
C5 C6 C7 121.9(10) .
C5 C6 H6 119.0 .
C7 C6 H6 119.1 .
C8 C7 C6 119.3(10) .
C8 C7 H7 120.3 .
C6 C7 H7 120.3 .
C7 C8 C9 119.1(9) .
C7 C8 N3 120.4(9) .
C9 C8 N3 120.5(9) .
C10 C9 C8 118.6(9) .
C10 C9 S1 117.6(8) .
C8 C9 S1 123.7(7) .
C9 C10 C5 125.1(10) .
C9 C10 H10 117.5 .
C5 C10 H10 117.4 .
N3 C11 C16 122.4(9) .
N3 C11 C12 123.7(8) .
C16 C11 C12 113.9(9) .
C13 C12 C11 122.9(9) .
C13 C12 S1 117.1(8) .
C11 C12 S1 119.5(7) .
C12 C13 C14 121.7(10) .
C12 C13 H13 119.1 .
C14 C13 H13 119.1 .
C15 C14 C13 115.9(10) .
C15 C14 C20 124.5(9) 2_566
C13 C14 C20 119.6(9) 2_566
C16 C15 C14 122.2(10) .
C16 C15 H15 118.9 .
C14 C15 H15 118.9 .
C15 C16 C11 123.1(10) .
C15 C16 H16 118.4 .
C11 C16 H16 118.4 .
F6 C17 F1 106.6(10) .
F6 C17 F2 106.3(10) .
F1 C17 F2 106.3(11) .
F6 C17 C18 112.7(12) .
F1 C17 C18 115.0(11) .
F2 C17 C18 109.3(10) .
O4 C18 C19 128.5(10) .
O4 C18 C17 112.3(9) .
C19 C18 C17 119.0(11) .
C18 C19 C20 126.3(11) .
C18 C19 H19 116.8 .
C20 C19 H19 116.8 .
O3 C20 C19 123.8(9) .
O3 C20 C14 116.5(8) 2_566
C19 C20 C14 119.7(9) 2_566
C25 C21 N1 116.8(15) .
C25 C21 H21 121.6 .
N1 C21 H21 121.6 .
C23 C22 N1 122.3(18) .
C23 C22 H22 118.8 .
N1 C22 H22 118.9 .
C22 C23 C24 122(2) .
C22 C23 H23 119.2 .
C24 C23 H23 119.2 .
C25 C24 C23 112.1(17) .
C25 C24 H24 123.9 .
C23 C24 H24 124.0 .
C21 C25 C24 126.9(18) .
C21 C25 H25 116.5 .
C24 C25 H25 116.6 .
C26 N2 C33 120.0 .
C26 N2 Mn1 137.98(6) .
C33 N2 Mn1 93.96(7) .
C27 C26 N2 120.0 .
C27 C26 H26 120.0 .
N2 C26 H26 120.0 .
C28 C27 C26 120.0 .
C28 C27 H27 120.0 .
C26 C27 H27 120.0 .
C29 C28 C27 120.0 .
C29 C28 H28 120.0 .
C27 C28 H28 120.0 .
C28 C29 C33 120.0 .
C28 C29 H29 120.0 .
C33 C29 H29 120.0 .
C29 C33 N2 120.0 .
C29 C33 H33 120.0 .
N2 C33 H33 120.0 .
N3 C30 C31 116.4 .
N3 C30 H30A 108.2 .
C31 C30 H30A 108.2 .
N3 C30 H30B 108.2 .
C31 C30 H30B 108.2 .
H30A C30 H30B 107.3 .
C30 C31 H31A 109.5 .
C30 C31 H31B 109.5 .
H31A C31 H31B 109.5 .
C30 C31 H31C 109.5 .
H31A C31 H31C 109.5 .
H31B C31 H31C 109.5 .
C22 N1 C21 120.1(11) .
C22 N1 Mn1 119.8(8) .
C21 N1 Mn1 120.0(8) .
C11 N3 C8 124.0(6) .
C11 N3 C30 117.4(4) .
C8 N3 C30 118.2(5) .
C2 O1 Mn1 127.9(5) .
C4 O2 Mn1 130.8(5) .
C20 O3 Mn1 129.4(5) .
C18 O4 Mn1 124.9(5) .
C9 S1 C12 101.8(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O1 2.094(3) .
Mn1 O2 2.119(3) .
Mn1 O3 2.127(3) .
Mn1 O4 2.127(3) .
Mn1 N1 2.263(3) .
Mn1 N2 2.513(4) .
C1 F3 1.235(18) .
C1 F4 1.262(15) .
C1 F5 1.32(2) .
C1 C2 1.512(16) .
C2 O1 1.260(13) .
C2 C3 1.369(16) .
C3 C4 1.403(15) .
C3 H3 0.9300 .
C4 O2 1.247(11) .
C4 C5 1.494(15) .
C5 C6 1.371(15) .
C5 C10 1.374(15) .
C6 C7 1.429(16) .
C6 H6 0.9300 .
C7 C8 1.375(16) .
C7 H7 0.9300 .
C8 C9 1.406(15) .
C8 N3 1.402(11) .
C9 C10 1.363(14) .
C9 S1 1.734(10) .
C10 H10 0.9300 .
C11 N3 1.379(10) .
C11 C16 1.409(15) .
C11 C12 1.420(14) .
C12 C13 1.339(15) .
C12 S1 1.771(10) .
C13 C14 1.419(15) .
C13 H13 0.9300 .
C14 C15 1.379(15) .
C14 C20 1.468(15) 2_566
C15 C16 1.352(16) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 F6 1.280(16) .
C17 F1 1.304(14) .
C17 F2 1.346(17) .
C17 C18 1.514(16) .
C18 O4 1.276(12) .
C18 C19 1.370(16) .
C19 C20 1.374(15) .
C19 H19 0.9300 .
C20 O3 1.267(10) .
C20 C14 1.468(15) 2_566
C21 C25 1.31(2) .
C21 N1 1.359(14) .
C21 H21 0.9300 .
C22 C23 1.27(2) .
C22 N1 1.362(14) .
C22 H22 0.9300 .
C23 C24 1.45(3) .
C23 H23 0.9300 .
C24 C25 1.38(3) .
C24 H24 0.9300 .
C25 H25 0.9300 .
N2 C26 1.3900 .
N2 C33 1.3900 .
C26 C27 1.3900 .
C26 H26 0.9300 .
C27 C28 1.3900 .
C27 H27 0.9300 .
C28 C29 1.3900 .
C28 H28 0.9300 .
C29 C33 1.3900 .
C29 H29 0.9300 .
C33 H33 0.9300 .
C30 N3 1.4726 .
C30 C31 1.4891 .
C30 H30A 0.9700 .
C30 H30B 0.9700 .
C31 H31A 0.9600 .
C31 H31B 0.9600 .
C31 H31C 0.9600 .
