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

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Monserrat, Jean-Philippe'
'Chabot, Guy'
'Hamon, Louis'
'Quentin, Lionel'
'Scherman, Daniel'
'Jaouen, Gerard'
'Hillard, Elizabeth'

_publ_contact_author_name        'Hillard, Elizabeth'
_publ_contact_author_email       elizabethhillard@yahoo.com

_publ_section_title              
;
Synthesis of Cytotoxic Ferrocenyl Flavones via a
Ferricenium-Mediated 1,6-Oxidative Cyclization
;

# Attachment 'compound-2c-corrected.cif'

data_compound_2c
_database_code_depnum_ccdc_archive 'CCDC 787468'
#TrackingRef 'compound-2c-corrected.cif'

_exptl_special_details           
;
The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107.
;
_refine_special_details          
;
?
;

_cell_length_a                   7.5434(7)
_cell_length_b                   14.7364(17)
_cell_length_c                   13.8726(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.146(8)
_cell_angle_gamma                90
_cell_volume                     1522.5(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a '
_symmetry_space_group_name_Hall  '-P 2yab'
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

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'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Fe 0.3463 0.8444 11.7695 4.7611 7.3573 0.3072 3.5222 15.3535 2.3045 76.8805
1.0369 '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'

_cell_formula_units_Z            4

# Given Formula = C20 Br2 O1
# Dc = 1.81 Fooo = 816.00 Mu = 53.23 M = 416.03
# Found Formula = C19 H13 Br1 Fe1 O2
# Dc = 1.78 FOOO = 816.00 Mu = 36.21 M = 409.06

_chemical_formula_sum            'C19 H13 Br1 Fe1 O2'
_chemical_formula_moiety         'C19 H13 Br1 Fe1 O2'
_chemical_compound_source        ?
_chemical_formula_weight         409.06

_cell_measurement_reflns_used    92
_cell_measurement_theta_min      5
_cell_measurement_theta_max      23
_cell_measurement_temperature    200

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.120
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_max          0.160

_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    3.621

# Sheldrick geometric approximatio 0.58 0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.65
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device       'Nonius KappaCCD'
_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       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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      200
_diffrn_reflns_number            21523
_reflns_number_total             3471
_diffrn_reflns_av_R_equivalents  0.059
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 3471
# Theoretical number of reflections is about 6996

_diffrn_reflns_theta_min         2.030
_diffrn_reflns_theta_max         27.500
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        26.400
_diffrn_measured_fraction_theta_full 0.995

_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   2.20
_oxford_diffrn_Wilson_scale      8.67

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

_refine_diff_density_min         -0.98
_refine_diff_density_max         0.96

# 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>-10.0\s(I)
_refine_ls_number_reflns         3465
_refine_ls_number_restraints     0
_refine_ls_number_parameters     209
_oxford_refine_ls_R_factor_ref   0.0644
_refine_ls_wR_factor_ref         0.0622
_refine_ls_goodness_of_fit_ref   0.9735
_refine_ls_shift/su_max          0.0008140

# The values computed from all data
_oxford_reflns_number_all        3465
_refine_ls_R_factor_all          0.0644
_refine_ls_wR_factor_all         0.0622

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                2507
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_gt          0.0506

# 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 Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    none # 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:
12.6 11.3 4.07
;
# 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.

Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.

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.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

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.
;

# 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
Br1 Br 0.70036(6) 0.68281(3) 0.12661(3) 0.0360 1.0000 Uani . . . . . . .
Fe2 Fe 0.80891(7) 0.58149(4) 0.83252(4) 0.0197 1.0000 Uani . . . . . . .
O3 O 0.6441(3) 0.60382(17) 0.54282(17) 0.0261 1.0000 Uani . . . . . . .
O4 O 0.8605(4) 0.41879(19) 0.45045(19) 0.0336 1.0000 Uani . . . . . . .
C5 C 0.6778(5) 0.4975(2) 0.7280(2) 0.0216 1.0000 Uani . . . . . . .
C6 C 0.5446(5) 0.5692(3) 0.8453(3) 0.0282 1.0000 Uani . . . . . . .
C7 C 0.7378(5) 0.5666(2) 0.3984(2) 0.0219 1.0000 Uani . . . . . . .
C8 C 1.0809(5) 0.5870(3) 0.8720(3) 0.0302 1.0000 Uani . . . . . . .
C9 C 0.7241(5) 0.4497(3) 0.8183(3) 0.0258 1.0000 Uani . . . . . . .
C10 C 0.7879(5) 0.4903(3) 0.4647(3) 0.0241 1.0000 Uani . . . . . . .
C11 C 0.7570(5) 0.5814(3) 0.3020(3) 0.0253 1.0000 Uani . . . . . . .
C12 C 0.5665(5) 0.5725(3) 0.7461(3) 0.0241 1.0000 Uani . . . . . . .
C13 C 0.9110(5) 0.7032(3) 0.7995(3) 0.0322 1.0000 Uani . . . . . . .
C14 C 0.6539(5) 0.6299(3) 0.4487(3) 0.0240 1.0000 Uani . . . . . . .
C15 C 0.9964(5) 0.6286(3) 0.9434(3) 0.0291 1.0000 Uani . . . . . . .
C16 C 0.7236(5) 0.5187(2) 0.5553(3) 0.0224 1.0000 Uani . . . . . . .
C17 C 0.6412(5) 0.4947(3) 0.8900(3) 0.0276 1.0000 Uani . . . . . . .
C18 C 0.5996(5) 0.7235(3) 0.3104(3) 0.0275 1.0000 Uani . . . . . . .
C19 C 0.5838(5) 0.7096(3) 0.4072(3) 0.0290 1.0000 Uani . . . . . . .
C20 C 0.7402(5) 0.4732(2) 0.6385(3) 0.0228 1.0000 Uani . . . . . . .
C21 C 1.0284(5) 0.6328(3) 0.7824(3) 0.0293 1.0000 Uani . . . . . . .
C22 C 0.8908(5) 0.7008(3) 0.8995(3) 0.0315 1.0000 Uani . . . . . . .
C23 C 0.6854(5) 0.6597(3) 0.2601(2) 0.0259 1.0000 Uani . . . . . . .
H61 H 0.4792 0.6126 0.8761 0.032(3) 1.0000 Uiso . . . . . . .
H81 H 1.1596 0.5352 0.8820 0.032(3) 1.0000 Uiso . . . . . . .
H91 H 0.8001 0.3978 0.8290 0.032(3) 1.0000 Uiso . . . . . . .
H111 H 0.8179 0.5382 0.2664 0.032(3) 1.0000 Uiso . . . . . . .
H121 H 0.5157 0.6168 0.6997 0.032(3) 1.0000 Uiso . . . . . . .
H131 H 0.8519 0.7453 0.7508 0.032(3) 1.0000 Uiso . . . . . . .
H151 H 1.0059 0.6101 1.0108 0.032(3) 1.0000 Uiso . . . . . . .
H171 H 0.6530 0.4778 0.9580 0.032(3) 1.0000 Uiso . . . . . . .
H181 H 0.5521 0.7778 0.2780 0.032(3) 1.0000 Uiso . . . . . . .
H191 H 0.5288 0.7537 0.4444 0.032(3) 1.0000 Uiso . . . . . . .
H201 H 0.7987 0.4155 0.6393 0.032(3) 1.0000 Uiso . . . . . . .
H211 H 1.0655 0.6177 0.7207 0.032(3) 1.0000 Uiso . . . . . . .
H221 H 0.8185 0.7408 0.9312 0.032(3) 1.0000 Uiso . . . . . . .
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
Br1 0.0461(3) 0.0395(2) 0.02369(19) 0.00495(19) 0.00924(17) -0.0048(2)
Fe2 0.0201(3) 0.0208(3) 0.0189(2) -0.0010(2) 0.00466(19) -0.0019(2)
O3 0.0333(15) 0.0273(15) 0.0183(13) -0.0001(11) 0.0057(11) 0.0067(12)
O4 0.0427(17) 0.0283(15) 0.0315(15) -0.0013(13) 0.0107(12) 0.0083(14)
C5 0.0224(19) 0.0219(19) 0.0199(17) 0.0006(14) 0.0012(14) -0.0026(15)
C6 0.0193(18) 0.034(2) 0.032(2) -0.0033(18) 0.0077(15) -0.0033(17)
C7 0.0207(18) 0.0233(19) 0.0212(17) -0.0021(15) 0.0022(14) -0.0024(15)
C8 0.0183(18) 0.035(2) 0.037(2) -0.0102(19) 0.0036(16) -0.0044(18)
C9 0.030(2) 0.0226(19) 0.0254(19) 0.0045(15) 0.0044(16) -0.0043(16)
C10 0.0233(19) 0.027(2) 0.0219(18) -0.0024(15) 0.0042(15) 0.0001(16)
C11 0.0243(18) 0.0267(19) 0.0254(18) -0.0019(17) 0.0057(14) -0.0033(17)
C12 0.0213(18) 0.027(2) 0.0236(18) 0.0001(16) 0.0025(14) -0.0011(16)
C13 0.036(2) 0.026(2) 0.037(2) -0.0006(17) 0.0116(18) -0.0124(18)
C14 0.0224(18) 0.026(2) 0.0228(19) -0.0009(15) 0.0007(15) -0.0044(16)
C15 0.0245(19) 0.036(2) 0.027(2) -0.0096(17) 0.0032(16) -0.0048(17)
C16 0.0218(19) 0.0212(19) 0.0234(18) -0.0006(15) 0.0012(14) -0.0016(15)
C17 0.027(2) 0.032(2) 0.0256(19) 0.0031(17) 0.0086(16) -0.0086(17)
C18 0.027(2) 0.028(2) 0.0273(19) 0.0043(16) 0.0027(16) 0.0017(16)
C19 0.029(2) 0.030(2) 0.030(2) 0.0011(17) 0.0103(17) 0.0056(17)
C20 0.0222(19) 0.0220(19) 0.0235(18) -0.0029(15) 0.0014(15) -0.0036(15)
C21 0.0245(19) 0.035(2) 0.031(2) -0.0053(17) 0.0123(16) -0.0111(17)
C22 0.032(2) 0.032(2) 0.034(2) -0.0150(18) 0.0134(17) -0.0105(18)
C23 0.030(2) 0.031(2) 0.0170(17) 0.0005(15) 0.0048(15) -0.0092(17)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3955(3)
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
Br1 . C23 . 1.904(3) yes
Fe2 . C5 . 2.038(4) yes
Fe2 . C6 . 2.038(4) yes
Fe2 . C8 . 2.039(4) yes
Fe2 . C9 . 2.045(4) yes
Fe2 . C12 . 2.025(3) yes
Fe2 . C13 . 2.033(4) yes
Fe2 . C15 . 2.039(4) yes
Fe2 . C17 . 2.048(4) yes
Fe2 . C21 . 2.040(4) yes
Fe2 . C22 . 2.037(4) yes
O3 . C14 . 1.374(4) yes
O3 . C16 . 1.390(4) yes
O4 . C10 . 1.218(4) yes
C5 . C9 . 1.431(5) yes
C5 . C12 . 1.434(5) yes
C5 . C20 . 1.442(5) yes
C6 . C12 . 1.413(5) yes
C6 . C17 . 1.406(5) yes
C6 . H61 . 0.950 no
C7 . C10 . 1.464(5) yes
C7 . C11 . 1.385(5) yes
C7 . C14 . 1.379(5) yes
C8 . C15 . 1.402(5) yes
C8 . C21 . 1.413(5) yes
C8 . H81 . 0.964 no
C9 . C17 . 1.421(5) yes
C9 . H91 . 0.953 no
C10 . C16 . 1.478(5) yes
C11 . C23 . 1.364(5) yes
C11 . H111 . 0.965 no
C12 . H121 . 0.953 no
C13 . C21 . 1.409(5) yes
C13 . C22 . 1.420(5) yes
C13 . H131 . 0.971 no
C14 . C19 . 1.376(5) yes
C15 . C22 . 1.408(6) yes
C15 . H151 . 0.965 no
C16 . C20 . 1.323(5) yes
C17 . H171 . 0.966 no
C18 . C19 . 1.381(5) yes
C18 . C23 . 1.391(5) yes
C18 . H181 . 0.959 no
C19 . H191 . 0.963 no
C20 . H201 . 0.957 no
C21 . H211 . 0.969 no
C22 . H221 . 0.957 no
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
C5 . Fe2 . C6 . 68.72(15) yes
C5 . Fe2 . C8 . 124.67(15) yes
C6 . Fe2 . C8 . 159.51(15) yes
C5 . Fe2 . C9 . 41.05(14) yes
C6 . Fe2 . C9 . 68.20(16) yes
C8 . Fe2 . C9 . 110.47(16) yes
C5 . Fe2 . C12 . 41.33(14) yes
C6 . Fe2 . C12 . 40.70(14) yes
C8 . Fe2 . C12 . 159.51(15) yes
C9 . Fe2 . C12 . 69.02(15) yes
C5 . Fe2 . C13 . 122.25(15) yes
C6 . Fe2 . C13 . 120.60(17) yes
C8 . Fe2 . C13 . 67.94(17) yes
C9 . Fe2 . C13 . 160.11(15) yes
C12 . Fe2 . C13 . 105.23(16) yes
C5 . Fe2 . C15 . 160.61(16) yes
C6 . Fe2 . C15 . 122.37(15) yes
C8 . Fe2 . C15 . 40.21(14) yes
C9 . Fe2 . C15 . 124.39(16) yes
C12 . Fe2 . C15 . 157.15(16) yes
C5 . Fe2 . C17 . 68.76(14) yes
C6 . Fe2 . C17 . 40.25(15) yes
C8 . Fe2 . C17 . 125.31(17) yes
C9 . Fe2 . C17 . 40.63(15) yes
C12 . Fe2 . C17 . 68.53(15) yes
C5 . Fe2 . C21 . 108.13(15) yes
C6 . Fe2 . C21 . 157.09(17) yes
C8 . Fe2 . C21 . 40.54(15) yes
C9 . Fe2 . C21 . 125.28(16) yes
C12 . Fe2 . C21 . 121.88(16) yes
C5 . Fe2 . C22 . 157.75(16) yes
C6 . Fe2 . C22 . 105.48(16) yes
C8 . Fe2 . C22 . 67.92(16) yes
C9 . Fe2 . C22 . 158.58(15) yes
C12 . Fe2 . C22 . 120.38(16) yes
C13 . Fe2 . C15 . 68.15(16) yes
C13 . Fe2 . C17 . 156.71(16) yes
C15 . Fe2 . C17 . 108.43(16) yes
C13 . Fe2 . C21 . 40.47(15) yes
C15 . Fe2 . C21 . 68.14(15) yes
C17 . Fe2 . C21 . 161.67(17) yes
C13 . Fe2 . C22 . 40.84(15) yes
C15 . Fe2 . C22 . 40.42(16) yes
C17 . Fe2 . C22 . 121.50(15) yes
C21 . Fe2 . C22 . 68.41(15) yes
C14 . O3 . C16 . 106.5(3) yes
Fe2 . C5 . C9 . 69.7(2) yes
Fe2 . C5 . C12 . 68.9(2) yes
C9 . C5 . C12 . 107.2(3) yes
Fe2 . C5 . C20 . 125.2(3) yes
C9 . C5 . C20 . 124.3(3) yes
C12 . C5 . C20 . 128.5(3) yes
Fe2 . C6 . C12 . 69.2(2) yes
Fe2 . C6 . C17 . 70.3(2) yes
C12 . C6 . C17 . 108.9(3) yes
Fe2 . C6 . H61 . 124.4 no
C12 . C6 . H61 . 124.3 no
C17 . C6 . H61 . 126.7 no
C10 . C7 . C11 . 132.2(3) yes
C10 . C7 . C14 . 107.2(3) yes
C11 . C7 . C14 . 120.6(4) yes
Fe2 . C8 . C15 . 69.9(2) yes
Fe2 . C8 . C21 . 69.8(2) yes
C15 . C8 . C21 . 108.5(4) yes
Fe2 . C8 . H81 . 125.3 no
C15 . C8 . H81 . 125.6 no
C21 . C8 . H81 . 125.8 no
C5 . C9 . Fe2 . 69.2(2) yes
C5 . C9 . C17 . 108.0(3) yes
Fe2 . C9 . C17 . 69.8(2) yes
C5 . C9 . H91 . 126.0 no
Fe2 . C9 . H91 . 125.2 no
C17 . C9 . H91 . 126.0 no
C7 . C10 . O4 . 129.8(3) yes
C7 . C10 . C16 . 103.3(3) yes
O4 . C10 . C16 . 126.9(3) yes
C7 . C11 . C23 . 116.7(3) yes
C7 . C11 . H111 . 121.4 no
C23 . C11 . H111 . 121.8 no
C5 . C12 . C6 . 107.8(3) yes
C5 . C12 . Fe2 . 69.8(2) yes
C6 . C12 . Fe2 . 70.1(2) yes
C5 . C12 . H121 . 126.4 no
C6 . C12 . H121 . 125.8 no
Fe2 . C12 . H121 . 125.7 no
Fe2 . C13 . C21 . 70.0(2) yes
Fe2 . C13 . C22 . 69.7(2) yes
C21 . C13 . C22 . 108.2(4) yes
Fe2 . C13 . H131 . 124.9 no
C21 . C13 . H131 . 125.8 no
C22 . C13 . H131 . 125.9 no
C7 . C14 . O3 . 112.9(3) yes
C7 . C14 . C19 . 122.9(4) yes
O3 . C14 . C19 . 124.2(3) yes
C8 . C15 . Fe2 . 69.9(2) yes
C8 . C15 . C22 . 108.2(3) yes
Fe2 . C15 . C22 . 69.7(2) yes
C8 . C15 . H151 . 126.1 no
Fe2 . C15 . H151 . 124.8 no
C22 . C15 . H151 . 125.6 no
C10 . C16 . O3 . 110.1(3) yes
C10 . C16 . C20 . 126.9(3) yes
O3 . C16 . C20 . 123.0(3) yes
C9 . C17 . C6 . 108.1(3) yes
C9 . C17 . Fe2 . 69.6(2) yes
C6 . C17 . Fe2 . 69.5(2) yes
C9 . C17 . H171 . 125.5 no
C6 . C17 . H171 . 126.4 no
Fe2 . C17 . H171 . 125.1 no
C19 . C18 . C23 . 120.4(3) yes
C19 . C18 . H181 . 119.7 no
C23 . C18 . H181 . 119.9 no
C18 . C19 . C14 . 116.5(4) yes
C18 . C19 . H191 . 122.1 no
C14 . C19 . H191 . 121.4 no
C5 . C20 . C16 . 128.8(4) yes
C5 . C20 . H201 . 115.1 no
C16 . C20 . H201 . 116.1 no
C8 . C21 . C13 . 107.5(3) yes
C8 . C21 . Fe2 . 69.7(2) yes
C13 . C21 . Fe2 . 69.5(2) yes
C8 . C21 . H211 . 126.1 no
C13 . C21 . H211 . 126.5 no
Fe2 . C21 . H211 . 125.5 no
C13 . C22 . C15 . 107.6(3) yes
C13 . C22 . Fe2 . 69.4(2) yes
C15 . C22 . Fe2 . 69.9(2) yes
C13 . C22 . H221 . 126.2 no
C15 . C22 . H221 . 126.2 no
Fe2 . C22 . H221 . 126.0 no
Br1 . C23 . C18 . 118.1(3) yes
Br1 . C23 . C11 . 119.1(3) yes
C18 . C23 . C11 . 122.8(3) yes