# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         222

loop_
_publ_author_name
'Catherine E Housecroft'
'Biljana Bozic-Weber'
'Edwin Constable'
'Markus Neuburger'
'Jason Price'

_publ_contact_author_name        'Catherine E Housecroft'
_publ_contact_author_email       CATHERINE.HOUSECROFT@UNIBAS.CH

_publ_section_title              
;
Sticky complexes: carboxylic acid-functionalized
N-phenylpyridin-2-ylmethanimine ligands as anchoring domains for
copper and ruthenium dye-sensitized solar cells
;

# Attachment 'jp162.cif'

data_jp162_123k
_database_code_depnum_ccdc_archive 'CCDC 756938'
#TrackingRef 'jp162.cif'

_audit_creation_date             09-07-14
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'jp162_123k_0m in P2(1)/c'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   13.2830(3)
_cell_length_b                   7.4327(2)
_cell_length_c                   21.8910(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.697(1)
_cell_angle_gamma                90
_cell_volume                     2080.66(8)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

# Given Formula = C18 H18 Cu1 F6 N4 O2 P1
# Dc = 1.69 Fooo = 1072.00 Mu = 12.04 M = 530.87
# Found Formula = C18 H18 Cu1 F6 N4 O2 P1
# Dc = 1.69 FOOO = 1072.00 Mu = 12.04 M = 530.87

_chemical_formula_sum            'C18 H18 Cu1 F6 N4 O2 P1'
_chemical_formula_moiety         'C18 H18 Cu N4 O2, F6 P'
_chemical_compound_source        ?
_chemical_formula_weight         530.87

_cell_measurement_reflns_used    9843
_cell_measurement_theta_min      3
_cell_measurement_theta_max      33
_cell_measurement_temperature    123

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.07
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.42

_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    1.204

# Sheldrick geometric approximatio 0.83 0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.92
_diffrn_measurement_device       'Bruker Kappa Apex2'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       '\f & \w scans'

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      123
_diffrn_reflns_number            46113
_reflns_number_total             7963
_diffrn_reflns_av_R_equivalents  0.025
# Number of reflections with Friedels Law is 7963
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 7990

_diffrn_reflns_theta_min         1.592
_diffrn_reflns_theta_max         33.230
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        33.230
_diffrn_measured_fraction_theta_full 0.995

_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_reflns_limit_h_min              -20
_reflns_limit_h_max              19
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              33

_oxford_diffrn_Wilson_B_factor   1.19
_oxford_diffrn_Wilson_scale      31.70

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.50

# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold

# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         6006
_refine_ls_number_restraints     0
_refine_ls_number_parameters     289
_oxford_refine_ls_R_factor_ref   0.0225
_refine_ls_wR_factor_ref         0.0239
_refine_ls_goodness_of_fit_ref   1.0702
_refine_ls_shift/su_max          0.002033

# The values computed from all data
_oxford_reflns_number_all        7948
_refine_ls_R_factor_all          0.0319
_refine_ls_wR_factor_all         0.0372

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                6563
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_gt          0.0249

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.129 0.836E-01 0.412E-01
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu21 Cu 0.187849(9) -0.069477(17) 0.391073(5) 0.0157 1.0000 Uani . . . . . . .
N1 N 0.16333(6) -0.23341(11) 0.31403(4) 0.0136 1.0000 Uani . . . . . . .
N2 N 0.26238(6) 0.08345(10) 0.33476(3) 0.0128 1.0000 Uani . . . . . . .
N3 N 0.07492(7) 0.05588(12) 0.41528(4) 0.0186 1.0000 Uani . . . . . . .
N4 N 0.28620(7) -0.12951(12) 0.47347(4) 0.0192 1.0000 Uani . . . . . . .
O1 O 0.47457(6) 0.57196(10) 0.24673(3) 0.0179 1.0000 Uani . . . . . . .
O2 O 0.46213(6) 0.79907(9) 0.31115(3) 0.0154 1.0000 Uani . . . . . . .
C1 C 0.07073(9) -0.46093(15) 0.35664(6) 0.0244 1.0000 Uani . . . . . . .
C2 C 0.11527(7) -0.39397(13) 0.30504(5) 0.0161 1.0000 Uani . . . . . . .
C3 C 0.10816(8) -0.49429(14) 0.25001(5) 0.0192 1.0000 Uani . . . . . . .
C4 C 0.15208(8) -0.42860(14) 0.20382(5) 0.0190 1.0000 Uani . . . . . . .
C5 C 0.20134(8) -0.26191(13) 0.21295(4) 0.0169 1.0000 Uani . . . . . . .
C6 C 0.20518(7) -0.16847(12) 0.26856(4) 0.0131 1.0000 Uani . . . . . . .
C7 C 0.25843(7) 0.00568(13) 0.28181(4) 0.0144 1.0000 Uani . . . . . . .
C8 C 0.35958(7) 0.35351(12) 0.31346(4) 0.0123 1.0000 Uani . . . . . . .
C9 C 0.31551(7) 0.24901(12) 0.35262(4) 0.0122 1.0000 Uani . . . . . . .
C10 C 0.32230(8) 0.30682(13) 0.41435(4) 0.0155 1.0000 Uani . . . . . . .
C11 C 0.37214(8) 0.46721(13) 0.43701(4) 0.0182 1.0000 Uani . . . . . . .
C12 C 0.41407(8) 0.57375(13) 0.39801(4) 0.0161 1.0000 Uani . . . . . . .
C13 C 0.40775(7) 0.51577(12) 0.33625(4) 0.0120 1.0000 Uani . . . . . . .
C14 C 0.45201(7) 0.62851(12) 0.29371(4) 0.0127 1.0000 Uani . . . . . . .
C15 C 0.02100(7) 0.13929(14) 0.43693(5) 0.0172 1.0000 Uani . . . . . . .
C16 C -0.04809(8) 0.24632(15) 0.46386(5) 0.0230 1.0000 Uani . . . . . . .
C17 C 0.34068(8) -0.13361(14) 0.52368(5) 0.0186 1.0000 Uani . . . . . . .
C18 C 0.41085(10) -0.13849(16) 0.58762(5) 0.0265 1.0000 Uani . . . . . . .
P1 P 0.248130(19) 0.31956(3) 0.592007(11) 0.0150 1.0000 Uani . . . . . . .
F1 F 0.30643(8) 0.50499(12) 0.61594(5) 0.0423 1.0000 Uani . . . . . . .
F2 F 0.18928(6) 0.13381(10) 0.56870(3) 0.0285 1.0000 Uani . . . . . . .
F3 F 0.18925(6) 0.41086(11) 0.52587(4) 0.0334 1.0000 Uani . . . . . . .
F4 F 0.34177(5) 0.26167(10) 0.56352(3) 0.0241 1.0000 Uani . . . . . . .
F5 F 0.30586(5) 0.22727(12) 0.65819(3) 0.0303 1.0000 Uani . . . . . . .
F6 F 0.15430(6) 0.37793(11) 0.62105(4) 0.0316 1.0000 Uani . . . . . . .
H13 H 0.0336 -0.5706 0.3462 0.0418 1.0000 Uiso R . . . . . .
H11 H 0.0207 -0.3758 0.3643 0.0415 1.0000 Uiso R . . . . . .
H12 H 0.1220 -0.4776 0.3963 0.0404 1.0000 Uiso R . . . . . .
H31 H 0.0744 -0.6065 0.2443 0.0230 1.0000 Uiso R . . . . . .
H41 H 0.1471 -0.4960 0.1674 0.0219 1.0000 Uiso R . . . . . .
H51 H 0.2309 -0.2122 0.1837 0.0215 1.0000 Uiso R . . . . . .
H71 H 0.2926 0.0654 0.2541 0.0187 1.0000 Uiso R . . . . . .
H81 H 0.3549 0.3174 0.2725 0.0153 1.0000 Uiso R . . . . . .
H101 H 0.2905 0.2355 0.4414 0.0212 1.0000 Uiso R . . . . . .
H111 H 0.3765 0.5030 0.4802 0.0241 1.0000 Uiso R . . . . . .
H121 H 0.4491 0.6841 0.4121 0.0198 1.0000 Uiso R . . . . . .
H162 H -0.0129 0.2793 0.5062 0.0382 1.0000 Uiso R . . . . . .
H161 H -0.1094 0.1789 0.4636 0.0377 1.0000 Uiso R . . . . . .
H163 H -0.0676 0.3507 0.4384 0.0381 1.0000 Uiso R . . . . . .
H182 H 0.3726 -0.1212 0.6154 0.0395 1.0000 Uiso R . . . . . .
H183 H 0.4606 -0.0446 0.5924 0.0393 1.0000 Uiso R . . . . . .
H181 H 0.4429 -0.2533 0.5952 0.0386 1.0000 Uiso R . . . . . .
H21 H 0.4856 0.8623 0.2887 0.0277 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu21 0.01885(5) 0.01677(5) 0.01327(5) -0.00114(4) 0.00720(4) -0.00137(4)
N1 0.0131(3) 0.0135(3) 0.0142(3) -0.0005(3) 0.0037(2) -0.0008(2)
N2 0.0141(3) 0.0120(3) 0.0128(3) -0.0004(2) 0.0042(2) -0.0010(2)
N3 0.0182(3) 0.0197(4) 0.0177(3) 0.0005(3) 0.0048(3) 0.0002(3)
N4 0.0226(4) 0.0171(3) 0.0183(3) -0.0011(3) 0.0061(3) 0.0031(3)
O1 0.0262(3) 0.0142(3) 0.0166(3) -0.0017(2) 0.0116(3) -0.0018(3)
O2 0.0206(3) 0.0105(3) 0.0176(3) -0.0009(2) 0.0093(2) -0.0021(2)
C1 0.0256(5) 0.0218(5) 0.0297(5) 0.0018(4) 0.0141(4) -0.0064(4)
C2 0.0140(4) 0.0143(4) 0.0200(4) -0.0003(3) 0.0043(3) -0.0014(3)
C3 0.0183(4) 0.0147(4) 0.0225(4) -0.0032(3) 0.0018(3) -0.0022(3)
C4 0.0217(4) 0.0169(4) 0.0160(4) -0.0044(3) 0.0006(3) 0.0008(3)
C5 0.0216(4) 0.0159(4) 0.0129(3) -0.0013(3) 0.0039(3) 0.0001(3)
C6 0.0146(3) 0.0130(3) 0.0114(3) -0.0005(3) 0.0029(3) -0.0005(3)
C7 0.0180(4) 0.0132(3) 0.0129(3) -0.0004(3) 0.0056(3) -0.0017(3)
C8 0.0134(3) 0.0124(3) 0.0112(3) -0.0005(3) 0.0036(3) -0.0003(3)
C9 0.0135(3) 0.0111(3) 0.0124(3) -0.0005(3) 0.0042(3) -0.0008(3)
C10 0.0214(4) 0.0138(4) 0.0132(3) -0.0012(3) 0.0078(3) -0.0018(3)
C11 0.0273(4) 0.0159(4) 0.0133(3) -0.0030(3) 0.0088(3) -0.0043(3)
C12 0.0219(4) 0.0132(3) 0.0144(3) -0.0023(3) 0.0067(3) -0.0029(3)
C13 0.0131(3) 0.0114(3) 0.0123(3) 0.0002(3) 0.0045(3) 0.0006(3)
C14 0.0131(3) 0.0111(3) 0.0138(3) 0.0001(3) 0.0038(3) 0.0004(3)
C15 0.0170(4) 0.0168(4) 0.0173(4) 0.0024(3) 0.0040(3) 0.0006(3)
C16 0.0222(4) 0.0212(4) 0.0279(5) -0.0003(4) 0.0108(4) 0.0054(4)
C17 0.0206(4) 0.0144(4) 0.0207(4) 0.0000(3) 0.0053(3) 0.0032(3)
C18 0.0280(5) 0.0223(5) 0.0226(5) 0.0013(4) -0.0042(4) 0.0026(4)
P1 0.01563(10) 0.01590(10) 0.01468(9) -0.00143(8) 0.00616(8) 0.00046(8)
F1 0.0515(5) 0.0293(4) 0.0543(5) -0.0208(4) 0.0285(4) -0.0198(4)
F2 0.0340(4) 0.0235(3) 0.0273(3) -0.0060(3) 0.0072(3) -0.0101(3)
F3 0.0336(4) 0.0384(4) 0.0293(3) 0.0173(3) 0.0104(3) 0.0147(3)
F4 0.0230(3) 0.0322(3) 0.0210(3) 0.0028(3) 0.0128(2) 0.0071(3)
F5 0.0242(3) 0.0524(5) 0.0135(3) 0.0060(3) 0.0038(2) 0.0039(3)
F6 0.0271(3) 0.0377(4) 0.0369(4) -0.0008(3) 0.0204(3) 0.0078(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.13438(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu21 . N1 . 2.0342(8) yes
Cu21 . N2 . 2.1100(8) yes
Cu21 . N3 . 1.9568(9) yes
Cu21 . N4 . 1.9708(9) yes
N1 . C2 . 1.3425(12) yes
N1 . C6 . 1.3538(11) yes
N2 . C7 . 1.2836(11) yes
N2 . C9 . 1.4198(12) yes
N3 . C15 . 1.1427(13) yes
N4 . C17 . 1.1413(13) yes
O1 . C14 . 1.2209(11) yes
O2 . C14 . 1.3204(11) yes
O2 . H21 . 0.802 no
C1 . C2 . 1.4949(14) yes
C1 . H13 . 0.948 no
C1 . H11 . 0.964 no
C1 . H12 . 0.956 no
C2 . C3 . 1.3981(14) yes
C3 . C4 . 1.3858(15) yes
C3 . H31 . 0.939 no
C4 . C5 . 1.3901(14) yes
C4 . H41 . 0.929 no
C5 . C6 . 1.3903(12) yes
C5 . H51 . 0.915 no
C6 . C7 . 1.4659(13) yes
C7 . H71 . 0.959 no
C8 . C9 . 1.3974(12) yes
C8 . C13 . 1.3929(12) yes
C8 . H81 . 0.922 no
C9 . C10 . 1.3974(12) yes
C10 . C11 . 1.3884(13) yes
C10 . H101 . 0.972 no
C11 . C12 . 1.3869(13) yes
C11 . H111 . 0.969 no
C12 . C13 . 1.3996(12) yes
C12 . H121 . 0.953 no
C13 . C14 . 1.4872(12) yes
C15 . C16 . 1.4544(14) yes
C16 . H162 . 0.951 no
C16 . H161 . 0.955 no
C16 . H163 . 0.950 no
C17 . C18 . 1.4571(14) yes
C18 . H182 . 0.901 no
C18 . H183 . 0.947 no
C18 . H181 . 0.948 no
P1 . F1 . 1.5982(8) yes
P1 . F2 . 1.6005(7) yes
P1 . F3 . 1.5987(7) yes
P1 . F4 . 1.5940(7) yes
P1 . F5 . 1.5990(7) yes
P1 . F6 . 1.6046(7) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 . Cu21 . N2 . 80.42(3) yes
N1 . Cu21 . N3 . 123.18(3) yes
N2 . Cu21 . N3 . 114.64(3) yes
N1 . Cu21 . N4 . 122.75(3) yes
N2 . Cu21 . N4 . 110.92(3) yes
N3 . Cu21 . N4 . 103.11(4) yes
Cu21 . N1 . C2 . 128.10(6) yes
Cu21 . N1 . C6 . 112.99(6) yes
C2 . N1 . C6 . 118.87(8) yes
Cu21 . N2 . C7 . 111.96(6) yes
Cu21 . N2 . C9 . 125.65(6) yes
C7 . N2 . C9 . 122.33(8) yes
Cu21 . N3 . C15 . 169.45(8) yes
Cu21 . N4 . C17 . 167.99(9) yes
C14 . O2 . H21 . 114.3 no
C2 . C1 . H13 . 113.0 no
C2 . C1 . H11 . 110.1 no
H13 . C1 . H11 . 105.6 no
C2 . C1 . H12 . 113.5 no
H13 . C1 . H12 . 107.7 no
H11 . C1 . H12 . 106.4 no
C1 . C2 . N1 . 117.06(9) yes
C1 . C2 . C3 . 121.68(9) yes
N1 . C2 . C3 . 121.26(9) yes
C2 . C3 . C4 . 119.82(9) yes
C2 . C3 . H31 . 120.5 no
C4 . C3 . H31 . 119.7 no
C3 . C4 . C5 . 118.93(9) yes
C3 . C4 . H41 . 119.4 no
C5 . C4 . H41 . 121.7 no
C4 . C5 . C6 . 118.39(9) yes
C4 . C5 . H51 . 122.3 no
C6 . C5 . H51 . 119.3 no
C5 . C6 . N1 . 122.72(8) yes
C5 . C6 . C7 . 121.05(8) yes
N1 . C6 . C7 . 116.20(8) yes
C6 . C7 . N2 . 118.43(8) yes
C6 . C7 . H71 . 124.7 no
N2 . C7 . H71 . 116.9 no
C9 . C8 . C13 . 119.31(8) yes
C9 . C8 . H81 . 120.4 no
C13 . C8 . H81 . 120.3 no
N2 . C9 . C8 . 124.91(8) yes
N2 . C9 . C10 . 115.47(8) yes
C8 . C9 . C10 . 119.62(8) yes
C9 . C10 . C11 . 120.62(8) yes
C9 . C10 . H101 . 119.7 no
C11 . C10 . H101 . 119.6 no
C10 . C11 . C12 . 120.16(8) yes
C10 . C11 . H111 . 118.8 no
C12 . C11 . H111 . 121.1 no
C11 . C12 . C13 . 119.31(8) yes
C11 . C12 . H121 . 122.3 no
C13 . C12 . H121 . 118.4 no
C12 . C13 . C8 . 120.95(8) yes
C12 . C13 . C14 . 120.06(8) yes
C8 . C13 . C14 . 118.99(7) yes
C13 . C14 . O2 . 112.73(7) yes
C13 . C14 . O1 . 124.21(8) yes
O2 . C14 . O1 . 123.04(8) yes
N3 . C15 . C16 . 179.41(10) yes
C15 . C16 . H162 . 109.8 no
C15 . C16 . H161 . 110.0 no
H162 . C16 . H161 . 109.5 no
C15 . C16 . H163 . 108.1 no
H162 . C16 . H163 . 110.2 no
H161 . C16 . H163 . 109.2 no
N4 . C17 . C18 . 179.60(12) yes
C17 . C18 . H182 . 108.3 no
C17 . C18 . H183 . 109.5 no
H182 . C18 . H183 . 108.9 no
C17 . C18 . H181 . 109.3 no
H182 . C18 . H181 . 108.6 no
H183 . C18 . H181 . 112.1 no
F1 . P1 . F2 . 179.39(4) yes
F1 . P1 . F3 . 90.33(5) yes
F2 . P1 . F3 . 90.02(4) yes
F1 . P1 . F4 . 90.05(4) yes
F2 . P1 . F4 . 90.45(4) yes
F3 . P1 . F4 . 90.15(4) yes
F1 . P1 . F5 . 90.11(5) yes
F2 . P1 . F5 . 89.54(4) yes
F3 . P1 . F5 . 179.38(4) yes
F4 . P1 . F5 . 90.29(4) yes
F1 . P1 . F6 . 89.79(5) yes
F2 . P1 . F6 . 89.71(4) yes
F3 . P1 . F6 . 90.11(4) yes
F4 . P1 . F6 . 179.70(4) yes
F5 . P1 . F6 . 89.46(4) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O2 . H21 . O1 3_655 160 0.80 1.88 2.6463(14) yes

# Attachment 'jp167.cif'

data_jp167
_database_code_depnum_ccdc_archive 'CCDC 756939'
#TrackingRef 'jp167.cif'

_publ_section_exptl_refinement   
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were
merged.

The absolute configuration was arbitrarily assigned.

The relatively large ratio of minimum to maximum corrections applied
in the multiscan process (1:nnn) reflect changes in the illuminated
volume of the crystal.

Changes in illuminated volume were kept to a minimum, and were
taken into account (G\"orbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry
(C---H in the range 0.93--0.98,
N---H in the range 0.86--0.89
N---H to 0.86
O---H = 0.82
\%A)
and
U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom),
after which the positions were refined with riding constraints.

;

_publ_section_exptl_prep         
# Brief details or a reference. Include solvent if known
;
?
;

# Hand-made tables can be put in the cif. The number of columns
# is set in the loop header.
# The contants of each column can either be a piece of text
# without any spaces (eg a number) or other text enclosed in " "
# Remove the leading # in the following example

#geom_extra_table_head_A
#;
#Table 2.
#Molecular parameters deviating most from MOGUL averages
#;
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
#_geom_extra_tableA_col_4
#
#Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d"
#N5-C6-C4 129 124 "7 (\%)"
#C3-O10-C2 105 109 "2 (\%)"
#C6-O7 1.25 1.22 ".02 (\%A)"
#
# End of 'script/refcif-b.dat'
#end of refcif
_cell_length_a                   18.2661(13)
_cell_length_b                   16.4632(13)
_cell_length_c                   12.4427(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.370(4)
_cell_angle_gamma                90
_cell_volume                     3710.8(4)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

# Given Formula = C34 H38 Cu1 F6 N6 O6 P1
# Dc = 1.49 Fooo = 1704.00 Mu = 7.14 M = 417.61
# Found Formula = C34 H34 Cu1 F6 N6 O6 P1
# Dc = 1.49 FOOO = 1704.00 Mu = 7.14 M = 415.59

_chemical_formula_sum            'C34 H38 Cu1 F6 N6 O6 P1'
_chemical_formula_moiety         'C28 H24 Cu N4 O4, F6 P, 2(C3 H7 N O)'
_chemical_compound_source        ?
_chemical_formula_weight         835.22

_cell_measurement_reflns_used    3414
_cell_measurement_theta_min      4
_cell_measurement_theta_max      23
_cell_measurement_temperature    123

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.02
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.28

_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             1704
_exptl_absorpt_coefficient_mu    0.714

# Sheldrick geometric approximatio 0.91 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device       'Bruker Kappa Apex2'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       '\f & \w scans'

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      123
_diffrn_reflns_number            27891
_reflns_number_total             4262
_diffrn_reflns_av_R_equivalents  0.100
# Number of reflections with Friedels Law is 4262
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 4267

_diffrn_reflns_theta_min         2.245
_diffrn_reflns_theta_max         27.509
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        27.509
_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -23
_reflns_limit_h_max              23
_reflns_limit_k_min              0
_reflns_limit_k_max              21
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   2.15
_oxford_diffrn_Wilson_scale      540.22

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.93
_refine_diff_density_max         0.59

# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold

# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     423
_refine_ls_number_parameters     281
_oxford_refine_ls_R_factor_ref   0.0684
_refine_ls_wR_factor_ref         0.0548
_refine_ls_goodness_of_fit_ref   1.0131
_refine_ls_shift/su_max          0.000669

# The values computed from all data
_oxford_reflns_number_all        4251
_refine_ls_R_factor_all          0.1125
_refine_ls_wR_factor_all         0.0814

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                2701
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_gt          0.0548

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.513 0.451 0.325
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint

# start Validation Reply Form
_vrf_PLAT430_1                   
;
PROBLEM: Short Inter D...A Contact O1 .. O4 .. 2.44 Ang.
RESPONSE: Hydrogen atoms could not be localized.
;
# end Validation Reply Form

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.0000 0.71660(4) 0.2500 0.0244 1.0000 Uani S T . . . . .
N1 N 0.08869(16) 0.64712(18) 0.2275(2) 0.0261 1.0000 Uani . . . . . . .
N2 N 0.02157(16) 0.76536(16) 0.1080(2) 0.0237 1.0000 Uani . . . . . . .
O1 O -0.13944(15) 1.04878(18) -0.1857(2) 0.0369 1.0000 Uani . . . . . . .
O2 O -0.18093(18) 1.0732(2) -0.0282(2) 0.0483 1.0000 Uani . . . . . . .
C1 C 0.0992(3) 0.5778(3) 0.4013(3) 0.0393 1.0000 Uani . . . . . . .
C2 C 0.1204(2) 0.5869(2) 0.2892(3) 0.0287 1.0000 Uani . . . . . . .
C3 C 0.1714(2) 0.5346(3) 0.2508(3) 0.0336 1.0000 Uani . . . . . . .
C4 C 0.1895(2) 0.5451(3) 0.1466(3) 0.0396 1.0000 Uani . . . . . . .
C5 C 0.1580(2) 0.6080(2) 0.0840(4) 0.0326 1.0000 Uani . . . . . . .
C6 C 0.10720(19) 0.6575(2) 0.1268(3) 0.0268 1.0000 Uani . . . . . . .
C7 C 0.0709(2) 0.7255(2) 0.0656(3) 0.0285 1.0000 Uani . . . . . . .
C8 C -0.01603(18) 0.8324(2) 0.0551(3) 0.0221 1.0000 Uani . . . . . . .
C9 C -0.0065(2) 0.8594(2) -0.0489(3) 0.0296 1.0000 Uani . . . . . . .
C10 C -0.04792(19) 0.9244(2) -0.0937(3) 0.0268 1.0000 Uani . . . . . . .
C11 C -0.09721(18) 0.9644(2) -0.0373(3) 0.0238 1.0000 Uani . . . . . . .
C12 C -0.1057(2) 0.9380(3) 0.0670(3) 0.0373 1.0000 Uani . . . . . . .
C13 C -0.0653(2) 0.8732(3) 0.1123(3) 0.0351 1.0000 Uani . . . . . . .
C14 C -0.1414(2) 1.0329(2) -0.0874(3) 0.0280 1.0000 Uani . . . . . . .
N3 N -0.29183(19) 1.2630(2) -0.2615(3) 0.0373 1.0000 Uani . . . . . . .
C15 C -0.3336(2) 1.3183(3) -0.2036(3) 0.0373 1.0000 Uani . . . . . . .
C16 C -0.3011(4) 1.2698(4) -0.3782(4) 0.0762 1.0000 Uani . . . . . . .
C17 C -0.2510(2) 1.2043(3) -0.2125(4) 0.0459 1.0000 Uani . . . . . . .
O3 O -0.2443(3) 1.2007(3) -0.1004(4) 0.0297 0.5000 Uani . . . . . . .
O4 O -0.2201(3) 1.1523(4) -0.2781(5) 0.0422 0.5000 Uani . . . . . . .
P1 P 0.0000 0.36217(9) 0.2500 0.0325 1.0000 Uani DS TU . . . . .
F1 F -0.0833(9) 0.3568(5) 0.1800(8) 0.0417 0.5000 Uani D U . . . . .
F2 F 0.0777(10) 0.3667(5) 0.3149(10) 0.0570 0.5000 Uani D U . . . . .
F3 F 0.0074(4) 0.4540(3) 0.2143(4) 0.0641 0.5000 Uani D U . . . . .
F4 F 0.0375(3) 0.3338(3) 0.1431(5) 0.0519 0.5000 Uani D U . . . . .
F5 F -0.0044(4) 0.2692(3) 0.2812(4) 0.0534 0.5000 Uani D U . . . . .
F6 F -0.0333(3) 0.3885(4) 0.3519(5) 0.0703 0.5000 Uani D U . . . . .
H11 H 0.1401 0.5562 0.4473 0.0590 1.0000 Uiso R . . . . . .
H12 H 0.0869 0.6300 0.4290 0.0596 1.0000 Uiso R . . . . . .
H13 H 0.0578 0.5418 0.4010 0.0594 1.0000 Uiso R . . . . . .
H31 H 0.1932 0.4930 0.2941 0.0393 1.0000 Uiso R . . . . . .
H41 H 0.2236 0.5093 0.1195 0.0461 1.0000 Uiso R . . . . . .
H51 H 0.1690 0.6163 0.0129 0.0422 1.0000 Uiso R . . . . . .
H71 H 0.0834 0.7390 -0.0033 0.0344 1.0000 Uiso R . . . . . .
H91 H 0.0274 0.8325 -0.0874 0.0362 1.0000 Uiso R . . . . . .
H101 H -0.0430 0.9424 -0.1632 0.0314 1.0000 Uiso R . . . . . .
H121 H -0.1387 0.9643 0.1064 0.0450 1.0000 Uiso R . . . . . .
H131 H -0.0712 0.8573 0.1831 0.0429 1.0000 Uiso R . . . . . .
H151 H -0.3196 1.3126 -0.1269 0.0578 1.0000 Uiso R . . . . . .
H152 H -0.3254 1.3739 -0.2246 0.0582 1.0000 Uiso R . . . . . .
H153 H -0.3855 1.3075 -0.2199 0.0582 1.0000 Uiso R . . . . . .
H161 H -0.2766 1.2250 -0.4083 0.1170 1.0000 Uiso R . . . . . .
H162 H -0.2798 1.3204 -0.3977 0.1171 1.0000 Uiso R . . . . . .
H163 H -0.3529 1.2691 -0.4061 0.1170 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0243(3) 0.0221(3) 0.0261(4) 0.0000 0.0005(3) 0.0000
N1 0.0259(15) 0.0216(15) 0.0285(16) -0.0007(13) -0.0049(12) -0.0039(12)
N2 0.0227(14) 0.0180(15) 0.0283(15) -0.0007(12) -0.0047(12) 0.0020(11)
O1 0.0429(15) 0.0448(17) 0.0233(13) 0.0102(13) 0.0045(11) 0.0072(14)
O2 0.0602(19) 0.0522(18) 0.0363(16) 0.0114(14) 0.0203(14) 0.0324(16)
C1 0.045(2) 0.038(2) 0.033(2) 0.0105(18) -0.0027(18) 0.007(2)
C2 0.0240(17) 0.0271(18) 0.033(2) 0.0036(16) -0.0033(15) 0.0013(15)
C3 0.0288(18) 0.0290(19) 0.040(2) 0.0052(18) -0.0059(16) 0.0037(17)
C4 0.0331(19) 0.036(2) 0.049(2) -0.003(2) 0.0040(18) 0.0058(19)
C5 0.028(2) 0.035(2) 0.035(2) -0.0045(17) 0.0035(17) 0.0039(16)
C6 0.0245(17) 0.0256(18) 0.0289(19) 0.0011(15) -0.0019(14) 0.0018(14)
C7 0.0291(17) 0.030(2) 0.0263(17) 0.0007(17) 0.0030(14) 0.0022(17)
C8 0.0206(16) 0.0223(17) 0.0223(16) -0.0025(14) -0.0017(13) -0.0010(13)
C9 0.0278(18) 0.037(2) 0.0241(18) 0.0024(16) 0.0026(15) 0.0026(16)
C10 0.0233(17) 0.0336(19) 0.0231(18) 0.0008(16) 0.0009(14) -0.0008(16)
C11 0.0212(15) 0.0269(17) 0.0214(16) -0.0004(15) -0.0053(12) -0.0046(15)
C12 0.045(2) 0.044(2) 0.0239(18) 0.0046(17) 0.0090(17) 0.0179(19)
C13 0.037(2) 0.042(2) 0.0263(19) 0.0044(17) 0.0057(16) 0.0161(19)
C14 0.0254(18) 0.0291(19) 0.0276(18) -0.0029(17) -0.0035(14) 0.0020(16)
N3 0.0403(19) 0.037(2) 0.0364(18) 0.0086(15) 0.0107(16) 0.0158(15)
C15 0.034(2) 0.041(2) 0.037(2) 0.0013(19) 0.0052(17) 0.0056(18)
C16 0.100(4) 0.097(4) 0.035(2) 0.016(3) 0.024(3) 0.066(3)
C17 0.031(2) 0.040(2) 0.067(3) 0.016(2) 0.007(2) 0.0021(19)
O3 0.030(2) 0.028(3) 0.030(3) 0.006(2) 0.001(2) 0.005(2)
O4 0.042(3) 0.050(3) 0.035(3) 0.009(3) 0.007(3) 0.021(3)
P1 0.0366(8) 0.0274(7) 0.0308(8) 0.0000 -0.0065(6) 0.0000
F1 0.037(4) 0.038(4) 0.043(4) 0.014(4) -0.022(3) -0.008(4)
F2 0.049(5) 0.042(4) 0.072(6) 0.005(4) -0.020(5) 0.009(4)
F3 0.070(3) 0.027(2) 0.084(5) 0.010(2) -0.031(4) -0.006(3)
F4 0.060(3) 0.058(3) 0.039(3) -0.008(3) 0.010(2) -0.007(3)
F5 0.049(3) 0.033(2) 0.075(5) 0.024(2) -0.004(4) -0.008(3)
F6 0.074(4) 0.097(5) 0.042(3) -0.021(4) 0.016(3) 0.010(4)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.05946(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 . N1 5_555 2.032(3) yes
Cu1 . N2 5_555 2.025(3) yes
Cu1 . N1 . 2.032(3) yes
Cu1 . N2 . 2.025(3) yes
N1 . C2 . 1.339(5) yes
N1 . C6 . 1.351(5) yes
N2 . C7 . 1.282(5) yes
N2 . C8 . 1.416(4) yes
O1 . C14 . 1.256(4) yes
O2 . C14 . 1.282(5) yes
C1 . C2 . 1.502(6) yes
C1 . H11 . 0.950 no
C1 . H12 . 0.962 no
C1 . H13 . 0.960 no
C2 . C3 . 1.397(6) yes
C3 . C4 . 1.388(6) yes
C3 . H31 . 0.929 no
C4 . C5 . 1.378(6) yes
C4 . H41 . 0.951 no
C5 . C6 . 1.390(5) yes
C5 . H51 . 0.942 no
C6 . C7 . 1.464(5) yes
C7 . H71 . 0.942 no
C8 . C9 . 1.400(5) yes
C8 . C13 . 1.390(5) yes
C9 . C10 . 1.385(5) yes
C9 . H91 . 0.941 no
C10 . C11 . 1.379(5) yes
C10 . H101 . 0.929 no
C11 . C12 . 1.396(5) yes
C11 . C14 . 1.476(5) yes
C12 . C13 . 1.376(5) yes
C12 . H121 . 0.931 no
C13 . H131 . 0.938 no
N3 . C15 . 1.439(5) yes
N3 . C16 . 1.444(6) yes
N3 . C17 . 1.321(5) yes
C15 . H151 . 0.960 no
C15 . H152 . 0.968 no
C15 . H153 . 0.961 no
C16 . H161 . 0.964 no
C16 . H162 . 0.964 no
C16 . H163 . 0.966 no
C17 . O3 . 1.386(7) yes
C17 . O4 . 1.354(8) yes
P1 . F1 . 1.656(17) yes
P1 . F2 . 1.54(2) yes
P1 . F3 . 1.586(5) yes
P1 . F4 . 1.640(6) yes
P1 . F5 . 1.584(4) yes
P1 . F6 . 1.537(6) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 5_555 Cu1 . N2 5_555 81.68(12) yes
N1 5_555 Cu1 . N1 . 111.46(17) yes
N2 5_555 Cu1 . N1 . 126.24(12) yes
N1 5_555 Cu1 . N2 . 126.24(12) yes
N2 5_555 Cu1 . N2 . 133.29(16) yes
N1 . Cu1 . N2 . 81.68(12) yes
Cu1 . N1 . C2 . 129.2(3) yes
Cu1 . N1 . C6 . 110.8(2) yes
C2 . N1 . C6 . 118.9(3) yes
Cu1 . N2 . C7 . 112.5(2) yes
Cu1 . N2 . C8 . 125.3(2) yes
C7 . N2 . C8 . 122.2(3) yes
C2 . C1 . H11 . 108.7 no
C2 . C1 . H12 . 110.1 no
H11 . C1 . H12 . 108.7 no
C2 . C1 . H13 . 110.9 no
H11 . C1 . H13 . 109.1 no
H12 . C1 . H13 . 109.4 no
C1 . C2 . N1 . 117.5(3) yes
C1 . C2 . C3 . 121.3(3) yes
N1 . C2 . C3 . 121.3(4) yes
C2 . C3 . C4 . 119.4(4) yes
C2 . C3 . H31 . 120.7 no
C4 . C3 . H31 . 119.9 no
C3 . C4 . C5 . 119.3(4) yes
C3 . C4 . H41 . 120.0 no
C5 . C4 . H41 . 120.7 no
C4 . C5 . C6 . 118.4(4) yes
C4 . C5 . H51 . 121.1 no
C6 . C5 . H51 . 120.5 no
C5 . C6 . N1 . 122.7(3) yes
C5 . C6 . C7 . 121.9(4) yes
N1 . C6 . C7 . 115.4(3) yes
C6 . C7 . N2 . 118.2(3) yes
C6 . C7 . H71 . 120.5 no
N2 . C7 . H71 . 121.3 no
N2 . C8 . C9 . 124.5(3) yes
N2 . C8 . C13 . 116.5(3) yes
C9 . C8 . C13 . 119.0(3) yes
C8 . C9 . C10 . 119.5(4) yes
C8 . C9 . H91 . 119.2 no
C10 . C9 . H91 . 121.3 no
C9 . C10 . C11 . 121.5(3) yes
C9 . C10 . H101 . 120.6 no
C11 . C10 . H101 . 117.9 no
C10 . C11 . C12 . 118.8(3) yes
C10 . C11 . C14 . 120.5(3) yes
C12 . C11 . C14 . 120.7(3) yes
C11 . C12 . C13 . 120.3(4) yes
C11 . C12 . H121 . 120.1 no
C13 . C12 . H121 . 119.6 no
C8 . C13 . C12 . 120.9(4) yes
C8 . C13 . H131 . 120.4 no
C12 . C13 . H131 . 118.7 no
C11 . C14 . O2 . 118.1(3) yes
C11 . C14 . O1 . 119.2(3) yes
O2 . C14 . O1 . 122.7(4) yes
C15 . N3 . C16 . 116.9(3) yes
C15 . N3 . C17 . 122.4(4) yes
C16 . N3 . C17 . 120.5(4) yes
N3 . C15 . H151 . 110.2 no
N3 . C15 . H152 . 110.6 no
H151 . C15 . H152 . 109.3 no
N3 . C15 . H153 . 110.4 no
H151 . C15 . H153 . 108.7 no
H152 . C15 . H153 . 107.6 no
N3 . C16 . H161 . 109.3 no
N3 . C16 . H162 . 108.8 no
H161 . C16 . H162 . 110.1 no
N3 . C16 . H163 . 110.1 no
H161 . C16 . H163 . 109.5 no
H162 . C16 . H163 . 109.1 no
N3 . C17 . O3 . 117.9(4) yes
N3 . C17 . O4 . 116.0(4) yes
O3 . C17 . O4 . 126.1(4) yes
F1 . P1 . F2 . 179.7(3) yes
F1 . P1 . F3 . 90.5(3) yes
F2 . P1 . F3 . 89.7(3) yes
F1 . P1 . F4 . 90.5(3) yes
F2 . P1 . F4 . 89.3(3) yes
F3 . P1 . F4 . 89.1(3) yes
F1 . P1 . F5 . 90.3(3) yes
F2 . P1 . F5 . 89.5(3) yes
F3 . P1 . F5 . 176.9(3) yes
F4 . P1 . F5 . 87.9(2) yes
F1 . P1 . F6 . 90.8(3) yes
F2 . P1 . F6 . 89.3(3) yes
F3 . P1 . F6 . 91.0(3) yes
F4 . P1 . F6 . 178.6(3) yes
F5 . P1 . F6 . 91.9(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C12 . H121 . O1 6_575 125 0.93 2.60 3.223(6) yes

# Attachment 'jp170.cif'

data_jp170
_database_code_depnum_ccdc_archive 'CCDC 756940'
#TrackingRef 'jp170.cif'

_audit_creation_date             09-08-18
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'jp170_123k_0m in P2(1)/n'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   14.0032(8)
_cell_length_b                   19.8547(13)
_cell_length_c                   15.4352(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.742(3)
_cell_angle_gamma                90
_cell_volume                     4216.2(5)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ru -1.2594 0.8363 19.2674 0.8085 12.9182 8.4347 4.8634 24.7997 1.5676 94.2928
5.3787 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

# Given Formula = C37 H32 F12 N8 O2 P2 Ru1
# Dc = 1.59 Fooo = 2049.64 Mu = 5.45 M = 1011.71
# Found Formula = C37.40 H32.60 F12 N8.20 O2 P2 Ru1
# Dc = 1.61 FOOO = 2049.64 Mu = 5.46 M = 1019.94

_chemical_formula_sum            'C37.40 H32.60 F12 N8.20 O2 P2 Ru1'
_chemical_formula_moiety         'C33 H26 N6 O2 Ru, 2(F6 P), 2.2(C2 H3 N)'
_chemical_compound_source        ?
_chemical_formula_weight         1019.94

_cell_measurement_reflns_used    9830
_cell_measurement_theta_min      3
_cell_measurement_theta_max      28
_cell_measurement_temperature    123

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_max          0.17

_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             2049.638
_exptl_absorpt_coefficient_mu    0.546

# Sheldrick geometric approximatio 0.98 0.98
# No experimental values of Tmin/max available
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device       'Bruker Kappa Apex2'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       '\f & \w scans'

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      123
_diffrn_reflns_number            81523
_reflns_number_total             10482
_diffrn_reflns_av_R_equivalents  0.054
# Number of reflections with Friedels Law is 10482
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 10505

_diffrn_reflns_theta_min         1.690
_diffrn_reflns_theta_max         28.326
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        28.326
_diffrn_measured_fraction_theta_full 0.997

_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -18
_reflns_limit_h_max              18
_reflns_limit_k_min              0
_reflns_limit_k_max              26
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   1.26
_oxford_diffrn_Wilson_scale      221.92

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.60
_refine_diff_density_max         1.99

# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold

# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         7564
_refine_ls_number_restraints     803
_refine_ls_number_parameters     586
_oxford_refine_ls_R_factor_ref   0.0390
_refine_ls_wR_factor_ref         0.0405
_refine_ls_goodness_of_fit_ref   1.0280
_refine_ls_shift/su_max          0.000923

# The values computed from all data
_oxford_reflns_number_all        10457
_refine_ls_R_factor_all          0.0580
_refine_ls_wR_factor_all         0.0593

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                7892
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_gt          0.0415

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.264 0.205 0.117
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Ru1 Ru 0.693051(13) 0.109364(9) 0.744325(12) 0.0133 1.0000 Uani . . . . . . .
N1 N 0.66280(14) 0.07448(10) 0.86184(13) 0.0159 1.0000 Uani . . . . . . .
N2 N 0.60972(15) 0.18611(10) 0.78054(14) 0.0162 1.0000 Uani . . . . . . .
N3 N 0.56554(15) 0.07617(10) 0.66638(14) 0.0161 1.0000 Uani . . . . . . .
N4 N 0.70542(15) 0.14837(10) 0.62245(13) 0.0158 1.0000 Uani . . . . . . .
N5 N 0.78048(16) 0.03155(11) 0.71778(13) 0.0184 1.0000 Uani . . . . . . .
N6 N 0.82642(15) 0.13904(11) 0.81291(14) 0.0181 1.0000 Uani . . . . . . .
O1 O 0.42872(14) 0.43898(10) 0.55207(14) 0.0290 1.0000 Uani . . . . . . .
O2 O 0.58731(14) 0.45574(10) 0.55282(14) 0.0272 1.0000 Uani . . . . . . .
C1 C 0.69730(19) 0.01842(13) 0.90443(17) 0.0211 1.0000 Uani . . . . . . .
C2 C 0.6731(2) -0.00072(15) 0.98428(18) 0.0255 1.0000 Uani . . . . . . .
C3 C 0.6103(2) 0.03931(15) 1.02132(18) 0.0255 1.0000 Uani . . . . . . .
C4 C 0.5732(2) 0.09768(13) 0.97777(17) 0.0231 1.0000 Uani . . . . . . .
C5 C 0.60134(17) 0.11412(13) 0.89915(16) 0.0183 1.0000 Uani . . . . . . .
C6 C 0.57150(18) 0.17538(13) 0.84964(17) 0.0191 1.0000 Uani . . . . . . .
C7 C 0.58441(18) 0.24618(12) 0.72978(16) 0.0168 1.0000 Uani . . . . . . .
C8 C 0.65954(18) 0.28459(12) 0.70805(17) 0.0190 1.0000 Uani . . . . . . .
C9 C 0.63802(19) 0.34199(13) 0.65699(18) 0.0213 1.0000 Uani . . . . . . .
C10 C 0.54102(19) 0.36052(12) 0.62766(17) 0.0197 1.0000 Uani . . . . . . .
C11 C 0.46637(19) 0.32119(13) 0.64901(18) 0.0223 1.0000 Uani . . . . . . .
C12 C 0.48748(19) 0.26363(13) 0.70020(18) 0.0218 1.0000 Uani . . . . . . .
C13 C 0.52127(19) 0.42280(13) 0.57383(17) 0.0214 1.0000 Uani . . . . . . .
C21 C 0.49717(19) 0.03910(13) 0.69464(17) 0.0206 1.0000 Uani . . . . . . .
C22 C 0.4098(2) 0.02301(14) 0.64129(19) 0.0257 1.0000 Uani . . . . . . .
C23 C 0.3909(2) 0.04626(15) 0.55552(19) 0.0270 1.0000 Uani . . . . . . .
C24 C 0.46101(19) 0.08403(15) 0.52481(18) 0.0246 1.0000 Uani . . . . . . .
C25 C 0.54803(18) 0.09813(12) 0.58122(16) 0.0172 1.0000 Uani . . . . . . .
C26 C 0.62779(18) 0.13756(12) 0.55610(16) 0.0171 1.0000 Uani . . . . . . .
C27 C 0.6251(2) 0.16330(14) 0.47178(17) 0.0246 1.0000 Uani . . . . . . .
C28 C 0.7026(2) 0.20170(15) 0.45492(18) 0.0273 1.0000 Uani . . . . . . .
C29 C 0.7814(2) 0.21251(15) 0.52225(19) 0.0260 1.0000 Uani . . . . . . .
C30 C 0.78076(19) 0.18469(13) 0.60447(17) 0.0213 1.0000 Uani . . . . . . .
C31 C 0.7500(2) -0.02446(14) 0.67155(18) 0.0245 1.0000 Uani . . . . . . .
C32 C 0.8139(3) -0.07079(15) 0.64657(19) 0.0321 1.0000 Uani . . . . . . .
C33 C 0.9123(3) -0.05939(18) 0.6701(2) 0.0381 1.0000 Uani . . . . . . .
C34 C 0.9447(2) -0.00302(18) 0.7195(2) 0.0339 1.0000 Uani . . . . . . .
C35 C 0.87808(19) 0.04164(14) 0.74406(17) 0.0224 1.0000 Uani . . . . . . .
C36 C 0.90382(18) 0.10072(14) 0.80099(17) 0.0217 1.0000 Uani . . . . . . .
C37 C 0.99809(19) 0.11581(17) 0.8437(2) 0.0300 1.0000 Uani . . . . . . .
C38 C 1.0133(2) 0.16981(17) 0.9008(2) 0.0327 1.0000 Uani . . . . . . .
C39 C 0.9351(2) 0.20698(15) 0.91590(19) 0.0272 1.0000 Uani . . . . . . .
C40 C 0.8426(2) 0.19065(13) 0.87066(17) 0.0221 1.0000 Uani . . . . . . .
N7 N 0.7587(6) 0.2961(3) 0.9956(3) 0.0767 0.7106 Uani D U . . . . .
C41 C 0.7383(4) 0.2650(2) 1.0498(3) 0.0430 0.7106 Uani D U . . . . .
C42 C 0.7066(4) 0.2255(3) 1.1163(3) 0.0435 0.7106 Uani D U . . . . .
N8 N 0.5026(4) 0.3124(3) 0.9439(4) 0.0486 0.5913 Uani D U . . . . .
C43 C 0.5182(5) 0.3427(3) 1.0072(4) 0.0461 0.5913 Uani D U . . . . .
C44 C 0.5427(7) 0.3778(6) 1.0834(5) 0.0861 0.5913 Uani D U . . . . .
N9 N 0.8374(6) 0.0371(4) 1.4523(5) 0.1268 0.8985 Uani D U . . . . .
C45 C 0.8269(5) 0.0649(3) 1.3853(4) 0.0703 0.8985 Uani D U . . . . .
C46 C 0.8053(4) 0.0974(3) 1.3041(4) 0.0657 0.8985 Uani D U . . . . .
P1 P 0.53658(5) -0.15371(3) 0.78959(5) 0.0221 1.0000 Uani . . . . . . .
F1 F 0.5881(2) -0.21879(12) 0.76006(15) 0.0601 1.0000 Uani . . . . . . .
F2 F 0.4872(2) -0.08782(11) 0.81974(17) 0.0614 1.0000 Uani . . . . . . .
F3 F 0.63842(17) -0.12686(17) 0.83870(17) 0.0697 1.0000 Uani . . . . . . .
F4 F 0.51979(16) -0.19122(10) 0.87698(12) 0.0412 1.0000 Uani . . . . . . .
F5 F 0.43510(17) -0.18014(16) 0.73814(15) 0.0640 1.0000 Uani . . . . . . .
F6 F 0.55211(16) -0.11613(10) 0.70041(13) 0.0425 1.0000 Uani . . . . . . .
P2 P 0.27247(5) 0.13602(4) 0.80656(5) 0.0276 1.0000 Uani . . . . . . .
F7 F 0.20899(18) 0.07103(13) 0.7770(2) 0.0652 1.0000 Uani . . . . . . .
F8 F 0.33507(17) 0.20293(12) 0.83577(19) 0.0573 1.0000 Uani . . . . . . .
F9 F 0.36519(15) 0.09041(12) 0.83989(15) 0.0477 1.0000 Uani . . . . . . .
F10 F 0.30218(19) 0.14139(13) 0.71209(14) 0.0557 1.0000 Uani . . . . . . .
F11 F 0.17935(16) 0.18236(12) 0.77433(14) 0.0492 1.0000 Uani . . . . . . .
F12 F 0.24321(16) 0.13319(11) 0.90149(13) 0.0446 1.0000 Uani . . . . . . .
H21 H 0.6992 -0.0402 1.0121 0.0301 1.0000 Uiso R . . . . . .
H31 H 0.5922 0.0273 1.0738 0.0308 1.0000 Uiso R . . . . . .
H41 H 0.5307 0.1252 1.0005 0.0278 1.0000 Uiso R . . . . . .
H61 H 0.5277 0.2048 0.8682 0.0230 1.0000 Uiso R . . . . . .
H81 H 0.7241 0.2726 0.7281 0.0228 1.0000 Uiso R . . . . . .
H91 H 0.6880 0.3675 0.6423 0.0253 1.0000 Uiso R . . . . . .
H111 H 0.4033 0.3338 0.6292 0.0267 1.0000 Uiso R . . . . . .
H121 H 0.4380 0.2369 0.7139 0.0266 1.0000 Uiso R . . . . . .
H211 H 0.5092 0.0247 0.7522 0.0251 1.0000 Uiso R . . . . . .
H221 H 0.3654 -0.0031 0.6635 0.0311 1.0000 Uiso R . . . . . .
H231 H 0.3308 0.0369 0.5186 0.0318 1.0000 Uiso R . . . . . .
H241 H 0.4503 0.0998 0.4672 0.0277 1.0000 Uiso R . . . . . .
H271 H 0.5721 0.1544 0.4272 0.0291 1.0000 Uiso R . . . . . .
H281 H 0.7022 0.2197 0.3997 0.0332 1.0000 Uiso R . . . . . .
H291 H 0.8334 0.2381 0.5130 0.0317 1.0000 Uiso R . . . . . .
H301 H 0.8346 0.1911 0.6497 0.0258 1.0000 Uiso R . . . . . .
H311 H 0.6832 -0.0317 0.6555 0.0287 1.0000 Uiso R . . . . . .
H321 H 0.7904 -0.1083 0.6155 0.0391 1.0000 Uiso R . . . . . .
H331 H 0.9553 -0.0892 0.6535 0.0468 1.0000 Uiso R . . . . . .
H341 H 1.0104 0.0052 0.7369 0.0409 1.0000 Uiso R . . . . . .
H371 H 1.0500 0.0904 0.8331 0.0358 1.0000 Uiso R . . . . . .
H381 H 1.0756 0.1809 0.9282 0.0389 1.0000 Uiso R . . . . . .
H391 H 0.9431 0.2423 0.9553 0.0319 1.0000 Uiso R . . . . . .
H401 H 0.7910 0.2161 0.8794 0.0257 1.0000 Uiso R . . . . . .
H421 H 0.7449 0.2354 1.1740 0.0681 0.7106 Uiso R . . . . . .
H423 H 0.6393 0.2348 1.1189 0.0683 0.7106 Uiso R . . . . . .
H422 H 0.7130 0.1776 1.1052 0.0680 0.7106 Uiso R . . . . . .
H442 H 0.4945 0.4109 1.0847 0.1210 0.5913 Uiso R . . . . . .
H441 H 0.5455 0.3463 1.1286 0.1209 0.5913 Uiso R . . . . . .
H443 H 0.6037 0.3970 1.0843 0.1209 0.5913 Uiso R . . . . . .
H462 H 0.8475 0.1341 1.3014 0.1051 0.8985 Uiso R . . . . . .
H463 H 0.7412 0.1151 1.2896 0.1049 0.8985 Uiso R . . . . . .
H461 H 0.8094 0.0703 1.2550 0.1051 0.8985 Uiso R . . . . . .
H11 H 0.7399 -0.0082 0.8805 0.0260 1.0000 Uiso R . . . . . .
H1 H 0.4230 0.4727 0.5213 0.0442 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ru1 0.01350(8) 0.01249(8) 0.01366(8) 0.00212(8) 0.00202(5) 0.00069(7)
N1 0.0148(9) 0.0163(9) 0.0158(9) 0.0012(7) 0.0007(7) 0.0008(7)
N2 0.0149(9) 0.0129(9) 0.0201(10) 0.0019(7) 0.0012(7) 0.0017(7)
N3 0.0167(9) 0.0128(9) 0.0184(9) 0.0003(7) 0.0023(7) 0.0002(7)
N4 0.0164(9) 0.0146(9) 0.0168(9) 0.0024(7) 0.0039(7) 0.0010(7)
N5 0.0223(10) 0.0175(10) 0.0160(9) 0.0029(8) 0.0053(8) 0.0035(8)
N6 0.0158(9) 0.0200(10) 0.0180(10) 0.0048(8) 0.0021(8) -0.0007(8)
O1 0.0227(9) 0.0215(9) 0.0420(12) 0.0154(8) 0.0038(8) 0.0044(8)
O2 0.0229(9) 0.0182(9) 0.0381(11) 0.0124(8) -0.0007(8) -0.0025(7)
C1 0.0219(12) 0.0204(12) 0.0208(12) 0.0035(9) 0.0033(9) 0.0038(10)
C2 0.0284(13) 0.0254(13) 0.0226(12) 0.0089(10) 0.0044(10) 0.0025(11)
C3 0.0315(14) 0.0285(13) 0.0178(12) 0.0044(10) 0.0076(10) -0.0014(11)
C4 0.0261(12) 0.0239(13) 0.0211(12) 0.0000(9) 0.0088(10) 0.0016(10)
C5 0.0184(10) 0.0179(11) 0.0184(10) 0.0012(9) 0.0024(8) 0.0011(9)
C6 0.0185(11) 0.0179(11) 0.0211(11) 0.0021(9) 0.0047(9) 0.0032(9)
C7 0.0199(11) 0.0123(10) 0.0179(11) 0.0014(8) 0.0022(9) 0.0019(9)
C8 0.0179(11) 0.0160(11) 0.0230(12) 0.0034(9) 0.0033(9) 0.0008(9)
C9 0.0219(12) 0.0145(11) 0.0267(13) 0.0027(9) 0.0027(10) -0.0009(9)
C10 0.0219(12) 0.0139(11) 0.0224(12) 0.0031(9) 0.0017(9) 0.0015(9)
C11 0.0184(11) 0.0206(12) 0.0269(13) 0.0072(10) 0.0017(10) 0.0045(9)
C12 0.0186(11) 0.0188(12) 0.0285(13) 0.0041(10) 0.0055(10) 0.0000(9)
C13 0.0235(12) 0.0150(11) 0.0241(12) 0.0028(9) 0.0006(10) 0.0015(9)
C21 0.0214(12) 0.0204(12) 0.0202(11) 0.0026(9) 0.0043(9) -0.0023(9)
C22 0.0206(12) 0.0268(13) 0.0302(14) 0.0023(11) 0.0061(10) -0.0064(10)
C23 0.0197(12) 0.0305(14) 0.0282(14) -0.0008(11) -0.0021(10) -0.0035(11)
C24 0.0221(12) 0.0292(13) 0.0208(12) 0.0018(10) -0.0001(10) 0.0003(10)
C25 0.0204(11) 0.0147(11) 0.0160(10) 0.0001(8) 0.0018(9) 0.0019(8)
C26 0.0184(11) 0.0152(10) 0.0176(11) 0.0014(9) 0.0028(9) 0.0034(9)
C27 0.0258(13) 0.0295(14) 0.0176(11) 0.0042(10) 0.0020(10) 0.0000(11)
C28 0.0328(14) 0.0301(14) 0.0198(12) 0.0083(11) 0.0071(11) -0.0006(11)
C29 0.0261(13) 0.0275(13) 0.0261(13) 0.0061(11) 0.0090(11) -0.0051(11)
C30 0.0212(12) 0.0212(12) 0.0211(12) 0.0013(9) 0.0032(10) -0.0021(9)
C31 0.0319(14) 0.0208(12) 0.0203(12) -0.0004(10) 0.0040(10) 0.0039(10)
C32 0.0500(18) 0.0238(13) 0.0221(13) -0.0028(10) 0.0055(12) 0.0118(13)
C33 0.0462(18) 0.0407(17) 0.0298(15) 0.0016(13) 0.0134(13) 0.0261(15)
C34 0.0284(14) 0.0446(17) 0.0298(15) 0.0040(13) 0.0081(12) 0.0146(13)
C35 0.0214(12) 0.0277(13) 0.0188(12) 0.0050(10) 0.0059(10) 0.0046(10)
C36 0.0184(11) 0.0280(14) 0.0197(11) 0.0053(10) 0.0058(9) -0.0001(10)
C37 0.0150(11) 0.0424(16) 0.0324(14) 0.0067(13) 0.0037(10) -0.0003(12)
C38 0.0181(12) 0.0442(17) 0.0331(15) 0.0066(13) -0.0020(11) -0.0100(12)
C39 0.0297(14) 0.0264(14) 0.0225(13) 0.0032(10) -0.0028(11) -0.0097(11)
C40 0.0250(13) 0.0207(12) 0.0197(12) 0.0037(9) 0.0015(10) -0.0048(10)
N7 0.155(5) 0.045(3) 0.037(2) 0.006(2) 0.033(3) 0.038(3)
C41 0.052(3) 0.036(2) 0.042(2) -0.0087(19) 0.012(2) 0.008(2)
C42 0.043(2) 0.038(2) 0.050(3) -0.005(2) 0.010(2) -0.006(2)
N8 0.054(3) 0.041(3) 0.053(3) -0.006(2) 0.015(2) 0.004(2)
C43 0.039(3) 0.048(3) 0.053(3) 0.002(3) 0.012(3) 0.012(3)
C44 0.073(4) 0.139(6) 0.042(3) -0.010(4) -0.001(3) -0.030(5)
N9 0.114(4) 0.101(4) 0.148(5) 0.025(4) -0.021(4) -0.010(4)
C45 0.069(3) 0.048(3) 0.087(3) -0.004(2) -0.004(3) 0.003(2)
C46 0.053(3) 0.060(3) 0.091(3) -0.002(3) 0.031(3) -0.002(2)
P1 0.0217(3) 0.0213(3) 0.0233(3) -0.0020(3) 0.0045(3) 0.0021(3)
F1 0.0948(19) 0.0445(12) 0.0433(12) -0.0058(10) 0.0186(12) 0.0355(12)
F2 0.101(2) 0.0327(10) 0.0644(15) 0.0108(10) 0.0510(14) 0.0293(12)
F3 0.0389(12) 0.111(2) 0.0555(14) -0.0280(14) 0.0001(10) -0.0261(14)
F4 0.0582(13) 0.0386(10) 0.0281(9) 0.0081(8) 0.0110(9) 0.0068(9)
F5 0.0408(12) 0.103(2) 0.0410(12) 0.0141(13) -0.0106(10) -0.0300(13)
F6 0.0552(12) 0.0402(11) 0.0370(10) 0.0050(9) 0.0214(9) -0.0049(9)
P2 0.0237(3) 0.0340(4) 0.0263(3) 0.0064(3) 0.0080(3) 0.0074(3)
F7 0.0472(13) 0.0532(14) 0.098(2) -0.0271(14) 0.0190(13) -0.0097(11)
F8 0.0474(13) 0.0480(13) 0.0832(17) -0.0101(12) 0.0295(12) -0.0094(10)
F9 0.0340(10) 0.0614(14) 0.0493(12) 0.0172(10) 0.0120(9) 0.0240(10)
F10 0.0717(15) 0.0680(15) 0.0346(11) 0.0138(10) 0.0280(10) 0.0320(13)
F11 0.0416(11) 0.0676(15) 0.0392(11) 0.0133(10) 0.0096(9) 0.0315(11)
F12 0.0497(12) 0.0551(12) 0.0342(10) 0.0180(9) 0.0209(9) 0.0211(10)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.07157(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ru1 . N1 . 2.058(2) yes
Ru1 . N2 . 2.059(2) yes
Ru1 . N3 . 2.066(2) yes
Ru1 . N4 . 2.071(2) yes
Ru1 . N5 . 2.059(2) yes
Ru1 . N6 . 2.054(2) yes
N1 . C1 . 1.337(3) yes
N1 . C5 . 1.370(3) yes
N2 . C6 . 1.297(3) yes
N2 . C7 . 1.435(3) yes
N3 . C21 . 1.343(3) yes
N3 . C25 . 1.363(3) yes
N4 . C26 . 1.364(3) yes
N4 . C30 . 1.349(3) yes
N5 . C31 . 1.347(3) yes
N5 . C35 . 1.366(3) yes
N6 . C36 . 1.365(3) yes
N6 . C40 . 1.349(3) yes
O1 . C13 . 1.317(3) yes
O1 . H1 . 0.816 no
O2 . C13 . 1.225(3) yes
C1 . C2 . 1.391(4) yes
C1 . H11 . 0.924 no
C2 . C3 . 1.385(4) yes
C2 . H21 . 0.935 no
C3 . C4 . 1.391(4) yes
C3 . H31 . 0.925 no
C4 . C5 . 1.383(3) yes
C4 . H41 . 0.924 no
C5 . C6 . 1.456(3) yes
C6 . H61 . 0.930 no
C7 . C8 . 1.390(3) yes
C7 . C12 . 1.393(3) yes
C8 . C9 . 1.386(3) yes
C8 . H81 . 0.931 no
C9 . C10 . 1.399(4) yes
C9 . H91 . 0.926 no
C10 . C11 . 1.393(4) yes
C10 . C13 . 1.487(3) yes
C11 . C12 . 1.390(4) yes
C11 . H111 . 0.914 no
C12 . H121 . 0.928 no
C21 . C22 . 1.379(4) yes
C21 . H211 . 0.918 no
C22 . C23 . 1.380(4) yes
C22 . H221 . 0.923 no
C23 . C24 . 1.388(4) yes
C23 . H231 . 0.942 no
C24 . C25 . 1.388(4) yes
C24 . H241 . 0.928 no
C25 . C26 . 1.474(3) yes
C26 . C27 . 1.392(3) yes
C27 . C28 . 1.390(4) yes
C27 . H271 . 0.931 no
C28 . C29 . 1.384(4) yes
C28 . H281 . 0.922 no
C29 . C30 . 1.386(4) yes
C29 . H291 . 0.921 no
C30 . H301 . 0.935 no
C31 . C32 . 1.387(4) yes
C31 . H311 . 0.932 no
C32 . C33 . 1.376(5) yes
C32 . H321 . 0.913 no
C33 . C34 . 1.383(5) yes
C33 . H331 . 0.915 no
C34 . C35 . 1.390(4) yes
C34 . H341 . 0.924 no
C35 . C36 . 1.470(4) yes
C36 . C37 . 1.394(4) yes
C37 . C38 . 1.379(5) yes
C37 . H371 . 0.924 no
C38 . C39 . 1.377(5) yes
C38 . H381 . 0.922 no
C39 . C40 . 1.390(4) yes
C39 . H391 . 0.922 no
C40 . H401 . 0.912 no
N7 . C41 . 1.119(6) yes
C41 . C42 . 1.427(6) yes
C42 . H421 . 0.971 no
C42 . H423 . 0.970 no
C42 . H422 . 0.973 no
N8 . C43 . 1.133(6) yes
C43 . C44 . 1.355(7) yes
C44 . H442 . 0.944 no
C44 . H441 . 0.933 no
C44 . H443 . 0.933 no
N9 . C45 . 1.158(7) yes
C45 . C46 . 1.392(6) yes
C46 . H462 . 0.944 no
C46 . H463 . 0.950 no
C46 . H461 . 0.941 no
P1 . F1 . 1.588(2) yes
P1 . F2 . 1.589(2) yes
P1 . F3 . 1.578(2) yes
P1 . F4 . 1.5962(19) yes
P1 . F5 . 1.583(2) yes
P1 . F6 . 1.616(2) yes
P2 . F7 . 1.585(3) yes
P2 . F8 . 1.609(2) yes
P2 . F9 . 1.588(2) yes
P2 . F10 . 1.593(2) yes
P2 . F11 . 1.598(2) yes
P2 . F12 . 1.594(2) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 . Ru1 . N2 . 77.85(8) yes
N1 . Ru1 . N3 . 96.22(8) yes
N2 . Ru1 . N3 . 85.54(8) yes
N1 . Ru1 . N4 . 172.79(8) yes
N2 . Ru1 . N4 . 96.75(8) yes
N3 . Ru1 . N4 . 78.46(8) yes
N1 . Ru1 . N5 . 98.66(8) yes
N2 . Ru1 . N5 . 175.79(8) yes
N3 . Ru1 . N5 . 97.24(8) yes
N4 . Ru1 . N5 . 86.92(8) yes
N1 . Ru1 . N6 . 87.66(8) yes
N2 . Ru1 . N6 . 98.90(8) yes
N3 . Ru1 . N6 . 174.66(8) yes
N4 . Ru1 . N6 . 97.98(8) yes
N5 . Ru1 . N6 . 78.50(9) yes
Ru1 . N1 . C1 . 126.79(17) yes
Ru1 . N1 . C5 . 115.21(16) yes
C1 . N1 . C5 . 118.0(2) yes
Ru1 . N2 . C6 . 116.32(16) yes
Ru1 . N2 . C7 . 124.18(16) yes
C6 . N2 . C7 . 119.2(2) yes
Ru1 . N3 . C21 . 125.21(17) yes
Ru1 . N3 . C25 . 116.11(16) yes
C21 . N3 . C25 . 118.5(2) yes
Ru1 . N4 . C26 . 115.66(16) yes
Ru1 . N4 . C30 . 126.00(17) yes
C26 . N4 . C30 . 118.3(2) yes
Ru1 . N5 . C31 . 125.68(19) yes
Ru1 . N5 . C35 . 115.46(17) yes
C31 . N5 . C35 . 118.6(2) yes
Ru1 . N6 . C36 . 116.06(17) yes
Ru1 . N6 . C40 . 125.65(18) yes
C36 . N6 . C40 . 118.2(2) yes
C13 . O1 . H1 . 109.5 no
N1 . C1 . C2 . 122.5(2) yes
N1 . C1 . H11 . 118.8 no
C2 . C1 . H11 . 118.7 no
C1 . C2 . C3 . 119.2(2) yes
C1 . C2 . H21 . 119.8 no
C3 . C2 . H21 . 121.0 no
C2 . C3 . C4 . 119.2(2) yes
C2 . C3 . H31 . 120.9 no
C4 . C3 . H31 . 119.9 no
C3 . C4 . C5 . 118.6(2) yes
C3 . C4 . H41 . 121.2 no
C5 . C4 . H41 . 120.2 no
C4 . C5 . N1 . 122.5(2) yes
C4 . C5 . C6 . 123.8(2) yes
N1 . C5 . C6 . 113.6(2) yes
C5 . C6 . N2 . 116.5(2) yes
C5 . C6 . H61 . 120.3 no
N2 . C6 . H61 . 123.2 no
N2 . C7 . C8 . 117.8(2) yes
N2 . C7 . C12 . 120.8(2) yes
C8 . C7 . C12 . 121.3(2) yes
C7 . C8 . C9 . 119.6(2) yes
C7 . C8 . H81 . 120.8 no
C9 . C8 . H81 . 119.6 no
C8 . C9 . C10 . 119.7(2) yes
C8 . C9 . H91 . 119.7 no
C10 . C9 . H91 . 120.6 no
C9 . C10 . C11 . 120.2(2) yes
C9 . C10 . C13 . 117.9(2) yes
C11 . C10 . C13 . 121.9(2) yes
C10 . C11 . C12 . 120.4(2) yes
C10 . C11 . H111 . 119.2 no
C12 . C11 . H111 . 120.4 no
C7 . C12 . C11 . 118.8(2) yes
C7 . C12 . H121 . 120.4 no
C11 . C12 . H121 . 120.8 no
C10 . C13 . O1 . 114.7(2) yes
C10 . C13 . O2 . 121.4(2) yes
O1 . C13 . O2 . 123.9(2) yes
N3 . C21 . C22 . 122.7(2) yes
N3 . C21 . H211 . 118.1 no
C22 . C21 . H211 . 119.2 no
C21 . C22 . C23 . 119.0(2) yes
C21 . C22 . H221 . 119.5 no
C23 . C22 . H221 . 121.4 no
C22 . C23 . C24 . 119.1(3) yes
C22 . C23 . H231 . 120.3 no
C24 . C23 . H231 . 120.6 no
C23 . C24 . C25 . 119.3(2) yes
C23 . C24 . H241 . 120.8 no
C25 . C24 . H241 . 119.9 no
C24 . C25 . N3 . 121.3(2) yes
C24 . C25 . C26 . 124.2(2) yes
N3 . C25 . C26 . 114.5(2) yes
C25 . C26 . N4 . 115.0(2) yes
C25 . C26 . C27 . 123.5(2) yes
N4 . C26 . C27 . 121.5(2) yes
C26 . C27 . C28 . 119.4(3) yes
C26 . C27 . H271 . 120.0 no
C28 . C27 . H271 . 120.6 no
C27 . C28 . C29 . 119.0(2) yes
C27 . C28 . H281 . 120.9 no
C29 . C28 . H281 . 120.1 no
C28 . C29 . C30 . 119.1(3) yes
C28 . C29 . H291 . 120.8 no
C30 . C29 . H291 . 120.1 no
C29 . C30 . N4 . 122.7(2) yes
C29 . C30 . H301 . 119.2 no
N4 . C30 . H301 . 118.1 no
N5 . C31 . C32 . 122.5(3) yes
N5 . C31 . H311 . 118.2 no
C32 . C31 . H311 . 119.3 no
C31 . C32 . C33 . 118.9(3) yes
C31 . C32 . H321 . 119.9 no
C33 . C32 . H321 . 121.2 no
C32 . C33 . C34 . 119.2(3) yes
C32 . C33 . H331 . 120.0 no
C34 . C33 . H331 . 120.8 no
C33 . C34 . C35 . 119.9(3) yes
C33 . C34 . H341 . 120.7 no
C35 . C34 . H341 . 119.4 no
C34 . C35 . N5 . 120.7(3) yes
C34 . C35 . C36 . 124.8(3) yes
N5 . C35 . C36 . 114.5(2) yes
C35 . C36 . N6 . 114.4(2) yes
C35 . C36 . C37 . 124.0(3) yes
N6 . C36 . C37 . 121.5(3) yes
C36 . C37 . C38 . 119.3(3) yes
C36 . C37 . H371 . 120.4 no
C38 . C37 . H371 . 120.3 no
C37 . C38 . C39 . 119.5(3) yes
C37 . C38 . H381 . 119.9 no
C39 . C38 . H381 . 120.7 no
C38 . C39 . C40 . 119.1(3) yes
C38 . C39 . H391 . 121.2 no
C40 . C39 . H391 . 119.8 no
C39 . C40 . N6 . 122.3(3) yes
C39 . C40 . H401 . 119.1 no
N6 . C40 . H401 . 118.6 no
N7 . C41 . C42 . 176.7(7) yes
C41 . C42 . H421 . 110.9 no
C41 . C42 . H423 . 111.2 no
H421 . C42 . H423 . 107.2 no
C41 . C42 . H422 . 111.1 no
H421 . C42 . H422 . 107.9 no
H423 . C42 . H422 . 108.4 no
N8 . C43 . C44 . 176.4(8) yes
C43 . C44 . H442 . 108.0 no
C43 . C44 . H441 . 105.8 no
H442 . C44 . H441 . 112.5 no
C43 . C44 . H443 . 107.8 no
H442 . C44 . H443 . 111.8 no
H441 . C44 . H443 . 110.6 no
N9 . C45 . C46 . 174.8(8) yes
C45 . C46 . H462 . 111.4 no
C45 . C46 . H463 . 114.9 no
H462 . C46 . H463 . 106.0 no
C45 . C46 . H461 . 115.1 no
H462 . C46 . H461 . 105.9 no
H463 . C46 . H461 . 102.7 no
F1 . P1 . F2 . 178.77(17) yes
F1 . P1 . F3 . 89.68(16) yes
F2 . P1 . F3 . 89.12(17) yes
F1 . P1 . F4 . 90.53(12) yes
F2 . P1 . F4 . 89.77(11) yes
F3 . P1 . F4 . 90.80(14) yes
F1 . P1 . F5 . 89.98(17) yes
F2 . P1 . F5 . 91.21(17) yes
F3 . P1 . F5 . 178.62(14) yes
F4 . P1 . F5 . 90.54(12) yes
F1 . P1 . F6 . 89.47(12) yes
F2 . P1 . F6 . 90.25(12) yes
F3 . P1 . F6 . 90.01(14) yes
F4 . P1 . F6 . 179.19(12) yes
F5 . P1 . F6 . 88.65(12) yes
F7 . P2 . F8 . 178.86(15) yes
F7 . P2 . F9 . 90.56(14) yes
F8 . P2 . F9 . 90.58(14) yes
F7 . P2 . F10 . 91.10(16) yes
F8 . P2 . F10 . 88.84(15) yes
F9 . P2 . F10 . 89.85(12) yes
F7 . P2 . F11 . 89.88(15) yes
F8 . P2 . F11 . 88.98(14) yes
F9 . P2 . F11 . 179.22(13) yes
F10 . P2 . F11 . 90.78(12) yes
F7 . P2 . F12 . 90.53(14) yes
F8 . P2 . F12 . 89.51(13) yes
F9 . P2 . F12 . 90.96(11) yes
F10 . P2 . F12 . 178.17(14) yes
F11 . P2 . F12 . 88.39(11) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C6 . H61 . N8 . 147 0.93 2.49 3.313(5) yes
C32 . H321 . N7 3_646 169 0.91 2.57 3.465(5) yes
C33 . H331 . N8 3_646 152 0.91 2.60 3.432(5) yes
C40 . H401 . N7 . 135 0.91 2.50 3.213(5) yes
C1 . H11 . O2 3_646 129 0.92 2.55 3.215(5) yes
O1 . H1 . O2 2_666 176 0.82 1.81 2.628(5) yes

# Attachment 'jp172.cif'

data_jp172
_database_code_depnum_ccdc_archive 'CCDC 756941'
#TrackingRef 'jp172.cif'

_audit_creation_date             09-11-19
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'jp172_123k_0ma in P2(1)/c'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   16.8253(9)
_cell_length_b                   9.7782(6)
_cell_length_c                   24.9831(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.754(3)
_cell_angle_gamma                90
_cell_volume                     4101.4(4)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ru -1.2594 0.8363 19.2674 0.8085 12.9182 8.4347 4.8634 24.7997 1.5676 94.2928
5.3787 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

# Given Formula = C34 H26 F12 N6 O2 P2 Ru1
# Dc = 1.52 Fooo = 1872.00 Mu = 5.53 M = 941.61
# Found Formula = C33 H26 F12 N6 O2.50 P2 Ru1
# Dc = 1.52 FOOO = 1872.00 Mu = 5.53 M = 937.60

_chemical_formula_sum            'C33 H27 F12 N6 O2.50 P2 Ru1'
_chemical_formula_moiety         'C33 H26 N6 O2 Ru, 2(F6 P), 0.5(H2 O)'
_chemical_compound_source        ?
_chemical_formula_weight         937.60

_cell_measurement_reflns_used    4774
_cell_measurement_theta_min      4
_cell_measurement_theta_max      28
_cell_measurement_temperature    123

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.11
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_max          0.29

_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             1872
_exptl_absorpt_coefficient_mu    0.553

# Sheldrick geometric approximatio 0.91 0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device       'Bruker Kappa Apex2'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       '\f & \w scans'

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      123
_diffrn_reflns_number            53770
_reflns_number_total             10249
_diffrn_reflns_av_R_equivalents  0.178
# Number of reflections with Friedels Law is 10249
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 10365

_diffrn_reflns_theta_min         1.634
_diffrn_reflns_theta_max         28.530
_diffrn_measured_fraction_theta_max 0.982

_diffrn_reflns_theta_full        27.959
_diffrn_measured_fraction_theta_full 0.999

_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_reflns_limit_h_min              -22
_reflns_limit_h_max              22
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              33

_oxford_diffrn_Wilson_B_factor   2.18
_oxford_diffrn_Wilson_scale      224.01

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -1.50
_refine_diff_density_max         1.95

# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold

# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         5473
_refine_ls_number_restraints     1194
_refine_ls_number_parameters     514
_oxford_refine_ls_R_factor_ref   0.1106
_refine_ls_wR_factor_ref         0.0870
_refine_ls_goodness_of_fit_ref   1.0306
_refine_ls_shift/su_max          0.003164

# The values computed from all data
_oxford_reflns_number_all        10225
_refine_ls_R_factor_all          0.1854
_refine_ls_wR_factor_all         0.1203

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                5473
_refine_ls_R_factor_gt           0.1106
_refine_ls_wR_factor_gt          0.0870

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
1.06 0.971 0.733
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint

_refine_special_details          
;
Crystal quality permitted to solve the structure, but refinement is not
satisfactory as the sof's suggest that the model shows some kind of average
structure. With the data we have there is no way of investigating more in
detail what is the nature of the problem and therefore it seems out of reach
with this dataset to enhance the model.
The hydrogen atoms of the partially occupied water molecule could not be
located.
;

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Ru1 Ru 0.18338(3) 0.80753(6) 0.63529(2) 0.0321 1.0000 Uani . U . . . . .
N1 N 0.2324(4) 0.7004(8) 0.7013(3) 0.0459 1.0000 Uani . U . . . . .
N2 N 0.3020(3) 0.8534(7) 0.6318(2) 0.0344 1.0000 Uani . U . . . . .
N3 N 0.1465(3) 0.9100(6) 0.5662(2) 0.0286 1.0000 Uani . U . . . . .
N4 N 0.1924(5) 0.6564(7) 0.5807(3) 0.0562 1.0000 Uani . U . . . . .
N5 N 0.0623(4) 0.7773(6) 0.6462(3) 0.0427 1.0000 Uani . U . . . . .
N6 N 0.1590(3) 0.9533(6) 0.6909(2) 0.0296 1.0000 Uani . U . . . . .
C1 C 0.1913(6) 0.6296(11) 0.7373(4) 0.0728 1.0000 Uani . U . . . . .
C2 C 0.2274(7) 0.5745(15) 0.7836(5) 0.1000 1.0000 Uani . U . . . . .
C3 C 0.3100(6) 0.5902(15) 0.7928(5) 0.0928 1.0000 Uani . U . . . . .
C4 C 0.3513(5) 0.6627(10) 0.7566(3) 0.0573 1.0000 Uani . U . . . . .
C5 C 0.3120(4) 0.7226(8) 0.7125(3) 0.0393 1.0000 Uani . U . . . . .
C6 C 0.3493(4) 0.8090(10) 0.6739(2) 0.0425 1.0000 Uani . U . . . . .
C7 C 0.4307(5) 0.8409(15) 0.6792(4) 0.0873 1.0000 Uani . U . . . . .
C8 C 0.4612(5) 0.9227(18) 0.6390(5) 0.1124 1.0000 Uani . U . . . . .
C9 C 0.4132(5) 0.9641(17) 0.5963(4) 0.0984 1.0000 Uani . U . . . . .
C10 C 0.3343(4) 0.9277(12) 0.5937(3) 0.0559 1.0000 Uani . U . . . . .
C11 C 0.1208(4) 1.0394(7) 0.5635(2) 0.0267 1.0000 Uani . U . . . . .
C12 C 0.0959(4) 1.1008(8) 0.5157(3) 0.0373 1.0000 Uani . U . . . . .
C13 C 0.0979(4) 1.0239(8) 0.4686(3) 0.0372 1.0000 Uani . U . . . . .
C14 C 0.1242(4) 0.8944(9) 0.4704(3) 0.0381 1.0000 Uani . U . . . . .
C15 C 0.1468(4) 0.8351(7) 0.5206(3) 0.0334 1.0000 Uani . U . . . . .
C16 C 0.1719(5) 0.6950(10) 0.5281(3) 0.0557 1.0000 Uani . U . . . . .
C17 C 0.1753(7) 0.5972(11) 0.4883(4) 0.0774 1.0000 Uani . U . . . . .
C18 C 0.1992(9) 0.4623(12) 0.4999(5) 0.1091 1.0000 Uani . U . . . . .
C19 C 0.2149(9) 0.4273(12) 0.5536(5) 0.1066 1.0000 Uani . U . . . . .
C20 C 0.2126(8) 0.5237(10) 0.5926(5) 0.0894 1.0000 Uani . U . . . . .
C21 C 0.0138(5) 0.6872(10) 0.6207(5) 0.0690 1.0000 Uani . U . . . . .
C22 C -0.0704(5) 0.6870(12) 0.6303(4) 0.0672 1.0000 Uani . U . . . . .
C23 C -0.1005(6) 0.7766(11) 0.6616(5) 0.0685 1.0000 Uani . U . . . . .
C24 C -0.0509(4) 0.8676(11) 0.6876(4) 0.0577 1.0000 Uani . U . . . . .
C25 C 0.0298(4) 0.8678(10) 0.6785(3) 0.0468 1.0000 Uani . U . . . . .
C26 C 0.0855(4) 0.9563(9) 0.7047(3) 0.0406 1.0000 Uani . U . . . . .
C27 C 0.2165(4) 1.0331(8) 0.7198(2) 0.0312 1.0000 Uani . U . . . . .
C28 C 0.2252(4) 1.0218(11) 0.7767(3) 0.0514 1.0000 Uani . U . . . . .
C29 C 0.2853(5) 1.0997(12) 0.8046(3) 0.0605 1.0000 Uani . U . . . . .
C30 C 0.3356(5) 1.1791(12) 0.7785(4) 0.0656 1.0000 Uani . U . . . . .
C31 C 0.3263(5) 1.1879(10) 0.7229(3) 0.0542 1.0000 Uani . U . . . . .
C32 C 0.2665(4) 1.1174(8) 0.6940(3) 0.0387 1.0000 Uani . U . . . . .
C33 C 0.3846(6) 1.2722(13) 0.6943(5) 0.0828 1.0000 Uani . U . . . . .
O1 O 0.4482(5) 1.3181(11) 0.7160(4) 0.1160 1.0000 Uani . U . . . . .
O2 O 0.3663(5) 1.2938(10) 0.6431(3) 0.1175 1.0000 Uani . U . . . . .
O3 O 0.4917(7) 1.3826(15) 0.5882(4) 0.0605 0.5000 Uani . . . . . . .
P1 P 0.32746(12) 1.1411(2) 0.44372(8) 0.0422 1.0000 Uani . U . . . . .
F1 F 0.3545(5) 1.2915(8) 0.4445(3) 0.1078 1.0000 Uani . U . . . . .
F2 F 0.3023(5) 0.9870(7) 0.4434(4) 0.1206 1.0000 Uani . U . . . . .
F3 F 0.2426(3) 1.1881(8) 0.4206(3) 0.0907 1.0000 Uani . U . . . . .
F4 F 0.2949(4) 1.1502(9) 0.5016(2) 0.0985 1.0000 Uani . U . . . . .
F5 F 0.4126(3) 1.0969(11) 0.4678(3) 0.1143 1.0000 Uani . U . . . . .
F6 F 0.3584(5) 1.1321(8) 0.3859(2) 0.0921 1.0000 Uani . U . . . . .
P2 P -0.00256(11) 1.2964(2) 0.65817(6) 0.0353 1.0000 Uani . U . . . . .
F7 F 0.0089(3) 1.4401(5) 0.68806(16) 0.0487 1.0000 Uani . U . . . . .
F8 F -0.0157(3) 1.1497(5) 0.62962(15) 0.0434 1.0000 Uani . U . . . . .
F9 F -0.0944(3) 1.3334(6) 0.6431(2) 0.0601 1.0000 Uani . U . . . . .
F10 F -0.0267(3) 1.2289(5) 0.71346(16) 0.0503 1.0000 Uani . U . . . . .
F11 F 0.0878(3) 1.2605(5) 0.6718(2) 0.0552 1.0000 Uani . U . . . . .
F12 F 0.0181(4) 1.3622(5) 0.60270(17) 0.0614 1.0000 Uani . U . . . . .
H11 H 0.1365 0.6187 0.7306 0.0890 1.0000 Uiso R . . . . . .
H21 H 0.1974 0.5269 0.8078 0.1279 1.0000 Uiso R . . . . . .
H31 H 0.3369 0.5518 0.8230 0.1059 1.0000 Uiso R . . . . . .
H41 H 0.4061 0.6726 0.7620 0.0658 1.0000 Uiso R . . . . . .
H71 H 0.4632 0.8110 0.7084 0.1061 1.0000 Uiso R . . . . . .
H81 H 0.5146 0.9473 0.6416 0.1400 1.0000 Uiso R . . . . . .
H91 H 0.4341 1.0156 0.5693 0.1219 1.0000 Uiso R . . . . . .
H101 H 0.3019 0.9575 0.5644 0.0649 1.0000 Uiso R . . . . . .
H111 H 0.1192 1.0896 0.5949 0.0322 1.0000 Uiso R . . . . . .
H121 H 0.0783 1.1914 0.5148 0.0460 1.0000 Uiso R . . . . . .
H131 H 0.0810 1.0628 0.4359 0.0461 1.0000 Uiso R . . . . . .
H141 H 0.1273 0.8442 0.4392 0.0471 1.0000 Uiso R . . . . . .
H171 H 0.1611 0.6212 0.4529 0.0921 1.0000 Uiso R . . . . . .
H181 H 0.2034 0.3980 0.4727 0.1281 1.0000 Uiso R . . . . . .
H191 H 0.2280 0.3376 0.5630 0.1369 1.0000 Uiso R . . . . . .
H201 H 0.2254 0.4987 0.6284 0.1058 1.0000 Uiso R . . . . . .
H211 H 0.0340 0.6250 0.5973 0.0799 1.0000 Uiso R . . . . . .
H221 H -0.1032 0.6206 0.6136 0.0740 1.0000 Uiso R . . . . . .
H231 H -0.1551 0.7788 0.6658 0.0760 1.0000 Uiso R . . . . . .
H241 H -0.0711 0.9290 0.7118 0.0751 1.0000 Uiso R . . . . . .
H261 H 0.0705 1.0158 0.7314 0.0471 1.0000 Uiso R . . . . . .
H281 H 0.1920 0.9644 0.7949 0.0600 1.0000 Uiso R . . . . . .
H291 H 0.2892 1.0980 0.8417 0.0709 1.0000 Uiso R . . . . . .
H301 H 0.3761 1.2267 0.7975 0.0741 1.0000 Uiso R . . . . . .
H321 H 0.2606 1.1267 0.6569 0.0469 1.0000 Uiso R . . . . . .
H2 H 0.3996 1.3449 0.6233 0.1422 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ru1 0.0295(2) 0.0337(3) 0.0313(3) 0.0014(3) -0.01297(18) 0.0005(3)
N1 0.042(2) 0.046(3) 0.047(2) 0.016(2) -0.019(2) 0.000(2)
N2 0.0269(14) 0.058(3) 0.018(2) -0.0033(18) -0.0017(15) 0.0116(19)
N3 0.027(2) 0.039(2) 0.0196(16) -0.0026(14) -0.0020(18) 0.005(2)
N4 0.065(3) 0.045(2) 0.053(2) -0.0151(18) -0.037(3) 0.020(3)
N5 0.0332(15) 0.041(3) 0.052(3) 0.0235(19) -0.0155(17) -0.0106(18)
N6 0.0225(17) 0.049(3) 0.0166(19) 0.0085(16) -0.0014(15) 0.0059(17)
C1 0.060(3) 0.068(5) 0.086(5) 0.049(4) -0.027(3) -0.024(4)
C2 0.067(3) 0.124(6) 0.105(5) 0.086(5) -0.027(4) -0.025(5)
C3 0.060(3) 0.130(6) 0.085(5) 0.066(5) -0.020(4) -0.003(5)
C4 0.037(3) 0.084(6) 0.049(4) 0.022(3) -0.011(3) 0.017(3)
C5 0.033(2) 0.052(4) 0.032(3) 0.004(2) -0.005(2) 0.018(2)
C6 0.025(2) 0.080(4) 0.023(3) 0.002(3) -0.0013(19) 0.014(3)
C7 0.024(2) 0.190(7) 0.047(4) 0.043(4) -0.005(3) 0.004(4)
C8 0.024(3) 0.224(7) 0.088(5) 0.074(5) 0.001(3) -0.006(5)
C9 0.029(3) 0.198(7) 0.070(5) 0.064(5) 0.014(3) 0.007(4)
C10 0.030(2) 0.120(6) 0.019(3) 0.012(3) 0.011(2) 0.014(3)
C11 0.029(3) 0.034(2) 0.017(2) 0.001(2) 0.008(2) -0.002(2)
C12 0.045(3) 0.038(3) 0.028(3) 0.006(2) -0.003(3) 0.001(3)
C13 0.041(3) 0.052(3) 0.019(2) 0.008(2) 0.006(3) -0.010(3)
C14 0.035(3) 0.061(3) 0.019(2) -0.009(2) 0.001(2) 0.002(3)
C15 0.031(3) 0.042(3) 0.026(2) -0.0098(17) -0.006(2) -0.001(3)
C16 0.061(4) 0.052(3) 0.049(3) -0.021(2) -0.032(3) 0.022(4)
C17 0.095(5) 0.074(4) 0.058(4) -0.035(3) -0.036(4) 0.043(5)
C18 0.153(5) 0.073(4) 0.091(4) -0.050(4) -0.072(5) 0.056(5)
C19 0.159(5) 0.056(4) 0.097(4) -0.031(3) -0.056(6) 0.044(5)
C20 0.134(5) 0.048(3) 0.077(4) -0.019(3) -0.062(5) 0.033(5)
C21 0.043(2) 0.039(4) 0.120(5) 0.014(3) -0.037(3) -0.008(3)
C22 0.047(3) 0.060(4) 0.089(5) 0.033(3) -0.031(3) -0.029(3)
C23 0.043(3) 0.074(5) 0.085(5) 0.043(3) -0.022(3) -0.015(3)
C24 0.028(2) 0.094(5) 0.049(4) 0.028(3) -0.008(2) -0.008(3)
C25 0.029(2) 0.072(4) 0.038(3) 0.026(2) -0.008(2) 0.000(2)
C26 0.0232(19) 0.077(4) 0.021(3) 0.010(3) 0.000(2) 0.009(2)
C27 0.023(2) 0.055(4) 0.016(2) -0.008(2) 0.0002(18) 0.0155(19)
C28 0.031(3) 0.106(5) 0.017(2) -0.004(3) -0.001(2) 0.016(3)
C29 0.043(3) 0.109(6) 0.027(3) -0.030(3) -0.012(2) 0.029(3)
C30 0.039(3) 0.105(5) 0.050(3) -0.031(4) -0.022(3) 0.014(3)
C31 0.048(3) 0.060(4) 0.051(3) -0.017(3) -0.023(3) 0.002(3)
C32 0.039(3) 0.045(4) 0.030(3) -0.002(3) -0.013(2) 0.001(2)
C33 0.064(4) 0.095(6) 0.083(4) 0.009(4) -0.043(3) -0.034(4)
O1 0.088(4) 0.131(6) 0.119(5) 0.015(5) -0.069(4) -0.056(4)
O2 0.101(4) 0.137(6) 0.105(4) 0.063(4) -0.071(3) -0.082(4)
O3 0.045(4) 0.104(7) 0.033(5) 0.002(5) 0.014(4) -0.033(5)
P1 0.0354(9) 0.0639(12) 0.0269(8) 0.0062(9) -0.0013(7) -0.0099(9)
F1 0.121(4) 0.086(2) 0.123(4) -0.028(3) 0.058(4) -0.062(3)
F2 0.110(4) 0.061(2) 0.193(6) 0.017(3) 0.028(4) -0.016(3)
F3 0.056(2) 0.126(4) 0.086(3) 0.036(4) -0.021(2) 0.010(3)
F4 0.095(3) 0.160(5) 0.044(2) 0.039(3) 0.033(2) 0.021(4)
F5 0.038(2) 0.230(5) 0.074(3) 0.043(4) -0.004(2) 0.008(3)
F6 0.131(4) 0.111(4) 0.038(2) 0.000(3) 0.027(2) 0.028(4)
P2 0.0388(9) 0.0468(10) 0.0202(7) 0.0016(8) 0.0008(6) 0.0098(9)
F7 0.069(3) 0.052(2) 0.0240(19) -0.0030(16) -0.0048(19) 0.003(2)
F8 0.054(2) 0.0515(19) 0.0239(18) -0.0052(15) 0.0001(17) 0.0098(18)
F9 0.0484(17) 0.074(3) 0.056(2) -0.019(2) -0.0143(18) 0.027(2)
F10 0.066(3) 0.062(3) 0.0237(16) -0.0001(16) 0.0105(17) -0.007(2)
F11 0.0363(16) 0.058(3) 0.070(3) 0.006(2) -0.0032(18) 0.0044(18)
F12 0.105(3) 0.054(3) 0.0269(18) 0.0094(17) 0.016(2) 0.014(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.0779(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ru1 . N1 . 2.078(6) yes
Ru1 . N2 . 2.054(6) yes
Ru1 . N3 . 2.056(5) yes
Ru1 . N4 . 2.023(7) yes
Ru1 . N5 . 2.094(6) yes
Ru1 . N6 . 2.051(6) yes
N1 . C1 . 1.359(12) yes
N1 . C5 . 1.367(9) yes
N2 . C6 . 1.348(8) yes
N2 . C10 . 1.340(10) yes
N3 . C11 . 1.338(9) yes
N3 . C15 . 1.355(8) yes
N4 . C16 . 1.388(10) yes
N4 . C20 . 1.370(12) yes
N5 . C21 . 1.333(10) yes
N5 . C25 . 1.339(11) yes
N6 . C26 . 1.306(9) yes
N6 . C27 . 1.405(9) yes
C1 . C2 . 1.380(13) yes
C1 . H11 . 0.932 no
C2 . C3 . 1.403(15) yes
C2 . H21 . 0.936 no
C3 . C4 . 1.374(14) yes
C3 . H31 . 0.932 no
C4 . C5 . 1.379(9) yes
C4 . H41 . 0.928 no
C5 . C6 . 1.455(11) yes
C6 . C7 . 1.402(10) yes
C7 . C8 . 1.408(15) yes
C7 . H71 . 0.930 no
C8 . C9 . 1.357(14) yes
C8 . H81 . 0.928 no
C9 . C10 . 1.371(12) yes
C9 . H91 . 0.930 no
C10 . H101 . 0.932 no
C11 . C12 . 1.378(9) yes
C11 . H111 . 0.927 no
C12 . C13 . 1.399(10) yes
C12 . H121 . 0.934 no
C13 . C14 . 1.341(12) yes
C13 . H131 . 0.928 no
C14 . C15 . 1.411(9) yes
C14 . H141 . 0.926 no
C15 . C16 . 1.442(11) yes
C16 . C17 . 1.384(12) yes
C17 . C18 . 1.404(15) yes
C17 . H171 . 0.930 no
C18 . C19 . 1.393(18) yes
C18 . H181 . 0.932 no
C19 . C20 . 1.359(15) yes
C19 . H191 . 0.930 no
C20 . H201 . 0.937 no
C21 . C22 . 1.452(13) yes
C21 . H211 . 0.924 no
C22 . C23 . 1.298(16) yes
C22 . H221 . 0.933 no
C23 . C24 . 1.357(14) yes
C23 . H231 . 0.933 no
C24 . C25 . 1.390(11) yes
C24 . H241 . 0.932 no
C25 . C26 . 1.405(11) yes
C26 . H261 . 0.932 no
C27 . C28 . 1.425(9) yes
C27 . C32 . 1.367(11) yes
C28 . C29 . 1.412(12) yes
C28 . H281 . 0.931 no
C29 . C30 . 1.349(15) yes
C29 . H291 . 0.925 no
C30 . C31 . 1.390(12) yes
C30 . H301 . 0.929 no
C31 . C32 . 1.383(10) yes
C31 . C33 . 1.498(15) yes
C32 . H321 . 0.932 no
C33 . O1 . 1.251(10) yes
C33 . O2 . 1.313(13) yes
O2 . H2 . 0.920 no
P1 . F1 . 1.539(7) yes
P1 . F2 . 1.565(7) yes
P1 . F3 . 1.573(5) yes
P1 . F4 . 1.582(6) yes
P1 . F5 . 1.577(6) yes
P1 . F6 . 1.571(6) yes
P2 . F7 . 1.598(5) yes
P2 . F8 . 1.610(5) yes
P2 . F9 . 1.608(5) yes
P2 . F10 . 1.607(4) yes
P2 . F11 . 1.576(5) yes
P2 . F12 . 1.587(5) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 . Ru1 . N2 . 78.9(2) yes
N1 . Ru1 . N3 . 173.7(2) yes
N2 . Ru1 . N3 . 95.6(2) yes
N1 . Ru1 . N4 . 97.1(3) yes
N2 . Ru1 . N4 . 90.8(3) yes
N3 . Ru1 . N4 . 79.7(2) yes
N1 . Ru1 . N5 . 99.5(2) yes
N2 . Ru1 . N5 . 173.3(3) yes
N3 . Ru1 . N5 . 86.3(2) yes
N4 . Ru1 . N5 . 95.8(3) yes
N1 . Ru1 . N6 . 84.2(3) yes
N2 . Ru1 . N6 . 96.6(2) yes
N3 . Ru1 . N6 . 99.6(2) yes
N4 . Ru1 . N6 . 172.5(3) yes
N5 . Ru1 . N6 . 76.7(2) yes
Ru1 . N1 . C1 . 126.1(5) yes
Ru1 . N1 . C5 . 114.5(5) yes
C1 . N1 . C5 . 118.7(6) yes
Ru1 . N2 . C6 . 114.9(5) yes
Ru1 . N2 . C10 . 126.2(4) yes
C6 . N2 . C10 . 118.8(6) yes
Ru1 . N3 . C11 . 125.6(4) yes
Ru1 . N3 . C15 . 115.2(5) yes
C11 . N3 . C15 . 119.2(5) yes
Ru1 . N4 . C16 . 114.5(5) yes
Ru1 . N4 . C20 . 125.1(7) yes
C16 . N4 . C20 . 120.4(8) yes
Ru1 . N5 . C21 . 126.9(7) yes
Ru1 . N5 . C25 . 115.1(5) yes
C21 . N5 . C25 . 117.6(8) yes
Ru1 . N6 . C26 . 115.4(5) yes
Ru1 . N6 . C27 . 124.9(4) yes
C26 . N6 . C27 . 119.0(6) yes
N1 . C1 . C2 . 122.6(9) yes
N1 . C1 . H11 . 118.7 no
C2 . C1 . H11 . 118.8 no
C1 . C2 . C3 . 118.2(10) yes
C1 . C2 . H21 . 120.7 no
C3 . C2 . H21 . 121.2 no
C2 . C3 . C4 . 119.2(8) yes
C2 . C3 . H31 . 120.8 no
C4 . C3 . H31 . 120.0 no
C3 . C4 . C5 . 120.6(8) yes
C3 . C4 . H41 . 120.0 no
C5 . C4 . H41 . 119.5 no
C4 . C5 . N1 . 120.6(7) yes
C4 . C5 . C6 . 124.8(7) yes
N1 . C5 . C6 . 114.6(6) yes
C5 . C6 . N2 . 116.5(6) yes
C5 . C6 . C7 . 121.8(6) yes
N2 . C6 . C7 . 121.7(8) yes
C6 . C7 . C8 . 117.3(8) yes
C6 . C7 . H71 . 121.7 no
C8 . C7 . H71 . 121.0 no
C7 . C8 . C9 . 120.2(9) yes
C7 . C8 . H81 . 119.5 no
C9 . C8 . H81 . 120.2 no
C8 . C9 . C10 . 119.0(10) yes
C8 . C9 . H91 . 119.9 no
C10 . C9 . H91 . 121.2 no
C9 . C10 . N2 . 123.0(7) yes
C9 . C10 . H101 . 118.1 no
N2 . C10 . H101 . 118.9 no
N3 . C11 . C12 . 122.4(6) yes
N3 . C11 . H111 . 119.0 no
C12 . C11 . H111 . 118.6 no
C11 . C12 . C13 . 118.2(7) yes
C11 . C12 . H121 . 120.8 no
C13 . C12 . H121 . 121.0 no
C12 . C13 . C14 . 120.3(6) yes
C12 . C13 . H131 . 119.8 no
C14 . C13 . H131 . 119.9 no
C13 . C14 . C15 . 119.2(6) yes
C13 . C14 . H141 . 120.6 no
C15 . C14 . H141 . 120.2 no
C14 . C15 . N3 . 120.6(7) yes
C14 . C15 . C16 . 124.5(6) yes
N3 . C15 . C16 . 114.9(6) yes
C15 . C16 . N4 . 115.7(7) yes
C15 . C16 . C17 . 126.0(8) yes
N4 . C16 . C17 . 118.2(8) yes
C16 . C17 . C18 . 121.7(9) yes
C16 . C17 . H171 . 119.2 no
C18 . C17 . H171 . 119.0 no
C17 . C18 . C19 . 117.6(10) yes
C17 . C18 . H181 . 121.2 no
C19 . C18 . H181 . 121.2 no
C18 . C19 . C20 . 120.6(11) yes
C18 . C19 . H191 . 120.2 no
C20 . C19 . H191 . 119.3 no
N4 . C20 . C19 . 121.3(10) yes
N4 . C20 . H201 . 119.4 no
C19 . C20 . H201 . 119.2 no
N5 . C21 . C22 . 119.7(11) yes
N5 . C21 . H211 . 119.9 no
C22 . C21 . H211 . 120.4 no
C21 . C22 . C23 . 121.4(9) yes
C21 . C22 . H221 . 118.8 no
C23 . C22 . H221 . 119.7 no
C22 . C23 . C24 . 118.6(9) yes
C22 . C23 . H231 . 120.7 no
C24 . C23 . H231 . 120.7 no
C23 . C24 . C25 . 119.9(11) yes
C23 . C24 . H241 . 119.6 no
C25 . C24 . H241 . 120.5 no
C24 . C25 . N5 . 122.6(8) yes
C24 . C25 . C26 . 123.6(9) yes
N5 . C25 . C26 . 113.7(7) yes
C25 . C26 . N6 . 118.5(8) yes
C25 . C26 . H261 . 121.0 no
N6 . C26 . H261 . 120.5 no
N6 . C27 . C28 . 119.4(7) yes
N6 . C27 . C32 . 121.2(6) yes
C28 . C27 . C32 . 119.4(7) yes
C27 . C28 . C29 . 118.3(8) yes
C27 . C28 . H281 . 120.6 no
C29 . C28 . H281 . 121.1 no
C28 . C29 . C30 . 121.6(7) yes
C28 . C29 . H291 . 119.1 no
C30 . C29 . H291 . 119.2 no
C29 . C30 . C31 . 119.0(8) yes
C29 . C30 . H301 . 120.3 no
C31 . C30 . H301 . 120.7 no
C30 . C31 . C32 . 121.4(9) yes
C30 . C31 . C33 . 118.4(8) yes
C32 . C31 . C33 . 120.2(8) yes
C31 . C32 . C27 . 120.3(7) yes
C31 . C32 . H321 . 119.8 no
C27 . C32 . H321 . 119.9 no
C31 . C33 . O1 . 123.9(10) yes
C31 . C33 . O2 . 115.7(7) yes
O1 . C33 . O2 . 120.3(11) yes
C33 . O2 . H2 . 119.9 no
F1 . P1 . F2 . 178.5(5) yes
F1 . P1 . F3 . 89.2(5) yes
F2 . P1 . F3 . 92.3(4) yes
F1 . P1 . F4 . 93.1(4) yes
F2 . P1 . F4 . 87.1(5) yes
F3 . P1 . F4 . 87.6(4) yes
F1 . P1 . F5 . 89.8(5) yes
F2 . P1 . F5 . 88.7(5) yes
F3 . P1 . F5 . 178.6(5) yes
F4 . P1 . F5 . 91.5(4) yes
F1 . P1 . F6 . 87.2(4) yes
F2 . P1 . F6 . 92.7(5) yes
F3 . P1 . F6 . 91.5(4) yes
F4 . P1 . F6 . 179.1(4) yes
F5 . P1 . F6 . 89.3(4) yes
F7 . P2 . F8 . 178.2(3) yes
F7 . P2 . F9 . 89.8(3) yes
F8 . P2 . F9 . 89.7(3) yes
F7 . P2 . F10 . 89.4(2) yes
F8 . P2 . F10 . 88.9(3) yes
F9 . P2 . F10 . 90.0(3) yes
F7 . P2 . F11 . 90.5(3) yes
F8 . P2 . F11 . 90.0(3) yes
F9 . P2 . F11 . 179.0(3) yes
F10 . P2 . F11 . 91.0(3) yes
F7 . P2 . F12 . 91.4(3) yes
F8 . P2 . F12 . 90.3(3) yes
F9 . P2 . F12 . 88.1(3) yes
F10 . P2 . F12 . 178.0(3) yes
F11 . P2 . F12 . 90.9(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C7 . H71 . O1 3_646 160 0.93 2.33 3.218(14) yes
O2 . H2 . O3 . 156 0.92 1.87 2.732(14) yes