# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012
data_General
_journal_name_full Org.Biomol.Chem.
_journal_coden_cambridge 0177
#TrackingRef '7921_web_deposit_cif_file_0_JunOU_1320126010.PC-O2-123-1_2-shelxl.cif'
_audit_creation_date 2011-Oct-28
_audit_creation_method SHELXL97
_audit_update_record
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2011-Oct-28 # Formatted by publCIF
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#==============================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)
_journal_date_recd_electronic ?
_journal_date_from_coeditor ?
_journal_date_accepted ?
_journal_coeditor_code ?
#==============================================================================
# SUBMISSION DETAILS
_publ_contact_author_name 'Dr. Pauline Chiu'
_publ_contact_author_email pchiu@hku.hk
_publ_contact_author_fax '(852)2859 8949'
_publ_contact_author_phone '(852)2915 5176'
_publ_contact_author_address
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Department of Chemistry
The University of Hong Kong
Pokfulam Road, Pokfulam,
Hong Kong SAR,
P. R. CHINA
;
_publ_contact_letter
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ENTER TEXT OF LETTER
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_publ_requested_category ? #'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name ?
#==============================================================================
# TITLE AND AUTHOR LIST
_publ_section_title
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Directory Reference: COM648 PC---Ou Jun's PC-O2-123-1_2 (Poly U collected)
9-Aug-2011
;
_publ_section_title_footnote .
loop_
_publ_author_footnote
_publ_author_address
.
;
Department of Chemistry
The University of Hong Kong
Pokfulam Road, Pokfulam,
Hong Kong SAR,
P. R. CHINA
;
.
;
Department of Chemistry
The University of Hong Kong
Pokfulam Road, Pokfulam,
Hong Kong SAR,
P. R. CHINA
;
.
;
Department of Chemistry
The University of Hong Kong
Pokfulam Road, Pokfulam,
Hong Kong SAR,
P. R. CHINA
;
_publ_section_synopsis .
#==============================================================================
# TEXT
_publ_section_abstract
;
(type here to add abstract)
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_publ_section_comment
;
The compound, 3(3a-hydroxy-7a-methyl-1-oxo-octahydro-inden-4-yl)-thioacrylic
acid S-ethyl ester,
crystallizes in a chiral primitive monoclinic space group, P2~1~ (#4).
The compound is chiral. There are 2 asymmetric units in the unit cell.
The cyclohexyl ring is in the chair form, and the five-membered ring in the
envelop form. The atoms C8 and C9 are R-configuration,
while atom C4 is S-configurations. All the bonding
parameters were within the normal ranges.
Inter-molecular, O3---H3O...O1 H-bond interaction is present in the crystal
lattice that connects the molecules into 1-D chain along a-axis.
The Flack parameter of the current configuration was found to be 0.1(2),
and for the inverted configuration was 0.9(2) which indicated that the
current configuration is the correct one.
;
_publ_section_references
;
Bruker AXS Inc. (2007). APEX II, Madison, Wisconsin, USA.
Bruker AXS Inc. (2007). SAINT, Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P.,
Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A.
(2008). Mercury J. Appl. Cryst, 41, 466--470.
Rigaku/MSC and Rigaku Corporation. (2006). CrystalStructure. Single
Crystal Structure Analysis Software. Version 3.8.1. Rigaku/MSC, 9009 New
Trails Drive, The Woodlands, TX, USA 77381-5209. Rigaku, 3-9-12 Akishima,
Tokyo 196-8666, Japan.
Sheldrick, G. M. (2008). SADABS, G\"ottingen University, G\"ottingen,
Germany.
Sheldrick, G. M. (2008). SHELX programs. SHELXL97 &
SHELXS97. Acta Cryst. E64, 112-122.
;
_publ_section_acknowledgements
;
Professor Z.-Y. Zhou, Dr. Wesley T.-K. Chan and the Hong Kong
Polytechnic University are sincerely thanked for helping the X-Ray data
collection.
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_publ_section_figure_captions
;
Fig. 1. The compound was shown at 50% probability thermal ellipsoids with
the atom numbering scheme (showing major component only).
Fig. 2. The unit cell packing diagram of the compound projected along the
b-axis and showing the H-bonding interactions (cyan lines) connecting
the molecules into 1-D chain along a-axis (showing major component
only).
;
_publ_section_exptl_prep
;
A colourless block crystal of C~22~H~22~O~3~S, having approximate dimensions of
0.16mm x 0.34mm x 0.76mm was mounted in glass capillary. All
measurements were made on a Bruker Apex II CCD detector with graphite
monochromated Mo---K\a radiation. The crystal-to-detector distance was 55.00
mm.
Cell constants and an orientation matrix for data collection corresponded to a
primitive monoclinic cell with dimensions: a = 6.8058(3) \%A, b = 8.7130(4)
\%A, c = 13.1696(5) \%A, V = 780.58(6) \%A^3^, \b = 91.746(3)\%.
For Z = 2 and F.W. = 282.40, the calculated density is 1.201 g/cm^3^.
Based on a statistical analysis of intensity distribution, and the successful
solution and refinement of the structure, the space group was determined to
be: P2~1~ (#4)
The data were collected at a temperature of 23(1)\%C to a maximum 2\q value of
50.05\%. The exposure rate was 20.0 [sec./\%]. The crystal-to-detector
distance was 55.00 mm.
Of the 7329 reflections that were collected, 2515 reflections were unique.
(R~int~ = 0.0291); equivalent reflections were merged.
;
_publ_section_exptl_refinement
;
The structure was solved by direct methods (SHELXS-97) and expanded
using Fourier techniques. All non-H atoms were refined anisotropically.
All of the C-bound H atoms were observable from difference Fourier map but were
all placed at geometrical positions with C---H = 0.93, 0.96, 0.97 and 0.98\%A
for vinyl, methyl, methylene and methine H-atoms respectively. All C-bound
H-atoms were refined using riding model with U~iso~(H) =
1.2U~eq~(Carrier). The O-bound hydrogen atoms were located from
difference Fourier map and also refined using riding model of
U~iso~(H) = 1.2U~eq~(Carrier).
The thio-ethyl group was refined as two disordered groups and their occupancies
were found to be 0.728(9) and 0.272(9) respectively.
Seventeen restraints have been used during the refinement. Twelve restraints
used in the anisotropic refinement of atoms C14 and C14' using isotropic
restraints of standard deviation of 0.01 (six restraints for each atom).
One restraint used to fix the C13---C14 distance to be 1.53(1)\%A. The bond
distances of the disordered group, thio-ethyl, were refined with same distance
restrants which accounted for three restraints. The final restraint was used
for the floating origin restraint.
Highest peak 0.39 at (-0.0007, 0.2208, 0.9729) [0.93 A from C12]
Deepest hole -0.28 at (0.1489, 0.6169, 0.9039) [0.72 A from S1']
;
loop_
_publ_author_name
'Jun Ou'
'Wing-Tak Wong'
P.Chiu
#============================================================================
data_PC-O2-123-1_2-shelxl
_database_code_depnum_ccdc_archive 'CCDC 851777'
#TrackingRef '7921_web_deposit_cif_file_0_JunOU_1320126010.PC-O2-123-1_2-shelxl.cif'
# PC-O2-123-1_2_Ou Jun_9-Aug-2011
_iucr_refine_instructions_details
;
TITL PC-O2-123-1_2_OuJun's(Collected2ndtimeatPolyU)_9-Aug-2011
CELL 0.71073 6.80580 8.71300 13.16960 90.000 91.746 90.000
ZERR 2 0.00030 0.00040 0.00050 0.000 0.003 0.000
LATT -1
SYMM -X, .50+Y, -Z
SFAC C H O S
UNIT 30 44 6 2
SHEL 8.000000 0.8400
OMIT 2 0 2
OMIT 5 -8 6
OMIT 0 0 2
L.S. 10
FMAP 2
PLAN -10
TWIN
BOND $H
EQIV $1_X-1,Y,Z
HTAB
HTAB O3 O1_$1
TEMP 23.0
EADP S1' S1
ACTA
SIZE 0.040 0.220 0.440
LIST 4
DFIX 1.5300 0.010 C13 C14
ISOR 0.01 0.02 C14 C14'
WGHT 0.110000 0.037300
BASF 0.11879
FVAR 1.17208 0.72811
PART 1
S1 4 0.125280 0.776761 -0.072664 21.00000 0.09684 0.20250 =
0.06793 0.05026 -0.01669 -0.03115
C13 1 -0.135228 0.803074 -0.097488 21.00000 0.11264 0.12504 =
0.08873 0.01034 -0.03757 -0.00676
AFIX 23
H13A 2 -0.196003 0.833012 -0.034827 21.00000 -1.20000
H13B 2 -0.153922 0.886499 -0.145588 21.00000 -1.20000
AFIX 0
C14 1 -0.237279 0.664060 -0.138588 21.00000 0.17640 0.17979 =
0.24510 -0.07665 -0.05787 -0.00341
AFIX 137
H14A 2 -0.161454 0.620113 -0.191562 21.00000 -1.20000
H14B 2 -0.364891 0.692183 -0.165547 21.00000 -1.20000
H14C 2 -0.251254 0.590305 -0.085137 21.00000 -1.20000
AFIX 0
PART 2
SAME S1 > C14
S1' 4 0.130108 0.687443 -0.069223 -21.00000 0.09684 0.20250 =
0.06793 0.05026 -0.01669 -0.03115
C13' 1 -0.120894 0.652691 -0.105948 -21.00000 0.11747 0.12760 =
0.04221 -0.00116 -0.00931 -0.00991
AFIX 23
H13C 2 -0.122716 0.581039 -0.162341 -21.00000 -1.20000
H13D 2 -0.183020 0.601941 -0.049762 -21.00000 -1.20000
AFIX 0
C14' 1 -0.243064 0.784999 -0.135849 -21.00000 0.17750 0.13580 =
0.18209 0.03650 -0.03003 -0.01976
AFIX 137
H14D 2 -0.228794 0.864068 -0.085396 -21.00000 -1.20000
H14E 2 -0.378277 0.753925 -0.141581 -21.00000 -1.20000
H14F 2 -0.202007 0.823520 -0.200121 -21.00000 -1.20000
AFIX 0
PART 0
O1 3 1.054079 0.874344 0.362463 11.00000 0.03034 0.09122 =
0.08849 -0.00910 0.00433 -0.00475
O2 3 -0.021266 0.733762 0.101380 11.00000 0.03837 0.20259 =
0.12964 0.02051 -0.00891 -0.00907
O3 3 0.402419 0.710389 0.420169 11.00000 0.03541 0.07157 =
0.06589 0.00076 0.01458 -0.00424
AFIX 1
H3O 2 0.284800 0.733600 0.415800 11.00000 -1.20000
AFIX 0
C1 1 0.875234 0.872395 0.366210 11.00000 0.03631 0.05926 =
0.05609 -0.00516 0.00402 -0.00467
C2 1 0.745876 0.997950 0.323049 11.00000 0.04074 0.06530 =
0.09886 0.01746 0.00215 -0.01172
AFIX 23
H2A 2 0.763070 1.008625 0.250544 11.00000 -1.20000
H2B 2 0.775911 1.095267 0.355753 11.00000 -1.20000
AFIX 0
C3 1 0.537768 0.947388 0.344823 11.00000 0.04227 0.05360 =
0.07677 0.00915 -0.00071 0.00837
AFIX 23
H3A 2 0.448633 0.972433 0.288368 11.00000 -1.20000
H3B 2 0.491616 0.996636 0.405700 11.00000 -1.20000
AFIX 0
C4 1 0.553746 0.689964 0.255300 11.00000 0.03624 0.06666 =
0.05078 0.00155 0.00124 -0.00299
AFIX 13
H4 2 0.651763 0.741234 0.214142 11.00000 -1.20000
AFIX 0
C5 1 0.616196 0.521372 0.267477 11.00000 0.05959 0.06677 =
0.06294 -0.01927 0.00227 0.00279
AFIX 23
H5A 2 0.526046 0.468716 0.311257 11.00000 -1.20000
H5B 2 0.611218 0.471130 0.201721 11.00000 -1.20000
AFIX 0
C6 1 0.821129 0.512237 0.312619 11.00000 0.05624 0.06189 =
0.07625 -0.00585 0.00458 0.01767
AFIX 23
H6A 2 0.911678 0.560923 0.267143 11.00000 -1.20000
H6B 2 0.859124 0.405431 0.320039 11.00000 -1.20000
AFIX 0
C7 1 0.834629 0.589871 0.414706 11.00000 0.04543 0.05934 =
0.06963 0.00052 -0.00305 0.00827
AFIX 23
H7A 2 0.971550 0.592417 0.437358 11.00000 -1.20000
H7B 2 0.764214 0.528061 0.462891 11.00000 -1.20000
AFIX 0
C8 1 0.552156 0.772160 0.359548 11.00000 0.02734 0.05091 =
0.05706 0.00366 0.00648 0.00268
C9 1 0.753652 0.752756 0.417209 11.00000 0.03346 0.05186 =
0.04880 -0.00118 0.00194 0.00365
C10 1 0.358747 0.704185 0.200281 11.00000 0.04551 0.08686 =
0.06079 -0.00519 -0.00570 -0.00665
AFIX 43
H10 2 0.248663 0.688796 0.239164 11.00000 -1.20000
AFIX 0
C11 1 0.324728 0.735144 0.105626 11.00000 0.05988 0.11590 =
0.05882 0.01080 -0.00745 -0.01019
AFIX 43
H11 2 0.430405 0.753647 0.064195 11.00000 -1.20000
AFIX 0
C12 1 0.119625 0.742275 0.060117 11.00000 0.07595 0.11611 =
0.06469 0.01237 0.00879 -0.01023
C15 1 0.742009 0.806941 0.528548 11.00000 0.05834 0.06859 =
0.05662 -0.00416 0.00152 -0.00351
AFIX 137
H15A 2 0.867935 0.794117 0.562323 11.00000 -1.20000
H15B 2 0.645613 0.747103 0.562627 11.00000 -1.20000
H15C 2 0.705242 0.913276 0.529887 11.00000 -1.20000
HKLF 4
REM PC-O2-123-1_2_OuJun's(Collected2ndtimeatPolyU)_9-Aug-2011
REM R1 = 0.0621 for 1908 Fo > 4sig(Fo) and 0.0816 for all 2515 data
REM 198 parameters refined using 17 restraints
END
WGHT 0.1126 0.0854
REM Highest difference peak 0.393, deepest hole -0.280, 1-sigma level 0.048
Q1 1 0.0007 0.7208 0.0271 11.00000 0.05 0.39
Q2 1 0.2186 0.7330 0.0031 11.00000 0.05 0.37
Q3 1 0.2842 0.7458 -0.0798 11.00000 0.05 0.30
Q4 1 0.5534 0.7184 0.3072 11.00000 0.05 0.20
Q5 1 -0.1752 0.7243 -0.0648 11.00000 0.05 0.18
Q6 1 -0.1919 0.7195 -0.1926 11.00000 0.05 0.18
Q7 1 -0.0158 0.7602 0.1180 11.00000 0.05 0.17
Q8 1 -0.2421 0.6697 -0.0925 11.00000 0.05 0.16
Q9 1 0.4301 0.7116 0.0666 11.00000 0.05 0.16
Q10 1 0.6351 0.7579 0.3884 11.00000 0.05 0.15
;
_audit_creation_method SHELXL-97
_chemical_absolute_configuration rmad
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C15 H22 O3 S'
_chemical_formula_sum 'C15 H22 O3 S'
_chemical_formula_weight 282.39
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21'
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_Int_Tables_number 4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 6.8058(3)
_cell_length_b 8.7130(4)
_cell_length_c 13.1696(5)
_cell_angle_alpha 90.00
_cell_angle_beta 91.746(3)
_cell_angle_gamma 90.00
_cell_volume 780.58(6)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 7329
_cell_measurement_theta_min 2.80
_cell_measurement_theta_max 25.03
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.44
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.04
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.201
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 304
_exptl_absorpt_coefficient_mu 0.209
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9137
_exptl_absorpt_correction_T_max 0.9917
_exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Apex CCD'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 7329
_diffrn_reflns_av_R_equivalents 0.0291
_diffrn_reflns_av_sigmaI/netI 0.0345
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 2.80
_diffrn_reflns_theta_max 25.03
_reflns_number_total 2515
_reflns_number_gt 1908
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'APEX (Bruker AXS Inc, 2007)'
_computing_cell_refinement 'SAINT v7.34A (Bruker AXS Inc, 2007)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2006)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'MERCURY (Macrae et al., 2008)'
_computing_publication_material 'SHELXL97 (Sheldrick, 2008)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1100P)^2^+0.0373P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack (1983). 1908 Friedel pairs'
_refine_ls_abs_structure_Flack 0.1(2)
_refine_ls_number_reflns 2515
_refine_ls_number_parameters 198
_refine_ls_number_restraints 17
_refine_ls_R_factor_all 0.0816
_refine_ls_R_factor_gt 0.0621
_refine_ls_wR_factor_ref 0.1852
_refine_ls_wR_factor_gt 0.1676
_refine_ls_goodness_of_fit_ref 1.102
_refine_ls_restrained_S_all 1.112
_refine_ls_shift/su_max 0.008
_refine_ls_shift/su_mean 0.001
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.1253(5) 0.7768(8) -0.0727(2) 0.1228(16) Uani 0.728(9) 1 d PD A 1
C13 C -0.1352(13) 0.8031(12) -0.0975(7) 0.110(3) Uani 0.728(9) 1 d PD A 1
H13A H -0.1960 0.8330 -0.0348 0.132 Uiso 0.728(9) 1 calc PR A 1
H13B H -0.1539 0.8865 -0.1456 0.132 Uiso 0.728(9) 1 calc PR A 1
C14 C -0.237(2) 0.6641(19) -0.1386(16) 0.202(8) Uani 0.728(9) 1 d PDU A 1
H14A H -0.1615 0.6201 -0.1916 0.242 Uiso 0.728(9) 1 calc PR A 1
H14B H -0.3649 0.6922 -0.1655 0.242 Uiso 0.728(9) 1 calc PR A 1
H14C H -0.2513 0.5903 -0.0851 0.242 Uiso 0.728(9) 1 calc PR A 1
S1' S 0.1301(15) 0.6874(19) -0.0692(8) 0.1228(16) Uani 0.272(9) 1 d PD A 2
C13' C -0.121(3) 0.653(3) -0.1059(14) 0.096(8) Uani 0.272(9) 1 d PD A 2
H13C H -0.1227 0.5810 -0.1623 0.115 Uiso 0.272(9) 1 calc PR A 2
H13D H -0.1830 0.6019 -0.0498 0.115 Uiso 0.272(9) 1 calc PR A 2
C14' C -0.243(5) 0.785(4) -0.136(4) 0.166(14) Uani 0.272(9) 1 d PDU A 2
H14D H -0.2288 0.8641 -0.0854 0.199 Uiso 0.272(9) 1 calc PR A 2
H14E H -0.3783 0.7539 -0.1416 0.199 Uiso 0.272(9) 1 calc PR A 2
H14F H -0.2020 0.8235 -0.2001 0.199 Uiso 0.272(9) 1 calc PR A 2
O1 O 1.0541(3) 0.8743(4) 0.3625(2) 0.0700(8) Uani 1 1 d . . .
O2 O -0.0213(5) 0.7338(7) 0.1014(3) 0.1238(17) Uani 1 1 d . A .
O3 O 0.4024(3) 0.7104(3) 0.42017(19) 0.0574(7) Uani 1 1 d . . .
H3O H 0.2848 0.7336 0.4158 0.069 Uiso 1 1 d . . .
C1 C 0.8752(5) 0.8724(5) 0.3662(3) 0.0505(8) Uani 1 1 d . . .
C2 C 0.7459(5) 0.9979(5) 0.3230(4) 0.0683(12) Uani 1 1 d . . .
H2A H 0.7631 1.0086 0.2505 0.082 Uiso 1 1 calc R . .
H2B H 0.7759 1.0953 0.3558 0.082 Uiso 1 1 calc R . .
C3 C 0.5378(5) 0.9474(4) 0.3448(3) 0.0576(10) Uani 1 1 d . . .
H3A H 0.4486 0.9724 0.2884 0.069 Uiso 1 1 calc R . .
H3B H 0.4916 0.9966 0.4057 0.069 Uiso 1 1 calc R . .
C4 C 0.5537(5) 0.6900(5) 0.2553(3) 0.0512(9) Uani 1 1 d . . .
H4 H 0.6518 0.7412 0.2141 0.061 Uiso 1 1 calc R . .
C5 C 0.6162(6) 0.5214(5) 0.2675(3) 0.0631(11) Uani 1 1 d . . .
H5A H 0.5260 0.4687 0.3113 0.076 Uiso 1 1 calc R . .
H5B H 0.6112 0.4711 0.2017 0.076 Uiso 1 1 calc R . .
C6 C 0.8211(6) 0.5122(5) 0.3126(3) 0.0647(11) Uani 1 1 d . . .
H6A H 0.9117 0.5609 0.2671 0.078 Uiso 1 1 calc R . .
H6B H 0.8591 0.4054 0.3200 0.078 Uiso 1 1 calc R . .
C7 C 0.8346(6) 0.5899(5) 0.4147(3) 0.0582(9) Uani 1 1 d . . .
H7A H 0.9715 0.5924 0.4374 0.070 Uiso 1 1 calc R . .
H7B H 0.7642 0.5281 0.4629 0.070 Uiso 1 1 calc R . .
C8 C 0.5522(4) 0.7722(4) 0.3595(2) 0.0450(8) Uani 1 1 d . . .
C9 C 0.7537(4) 0.7528(4) 0.4172(2) 0.0447(8) Uani 1 1 d . . .
C10 C 0.3587(6) 0.7042(5) 0.2003(3) 0.0645(11) Uani 1 1 d . . .
H10 H 0.2487 0.6888 0.2392 0.077 Uiso 1 1 calc R . .
C11 C 0.3247(7) 0.7351(7) 0.1056(3) 0.0784(14) Uani 1 1 d . A .
H11 H 0.4304 0.7536 0.0642 0.094 Uiso 1 1 calc R . .
C12 C 0.1196(8) 0.7423(7) 0.0601(4) 0.0854(15) Uani 1 1 d . . .
C15 C 0.7420(6) 0.8069(6) 0.5285(3) 0.0612(10) Uani 1 1 d . . .
H15A H 0.8679 0.7941 0.5623 0.073 Uiso 1 1 calc R . .
H15B H 0.6456 0.7471 0.5626 0.073 Uiso 1 1 calc R . .
H15C H 0.7052 0.9133 0.5299 0.073 Uiso 1 1 calc 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
S1 0.0968(12) 0.203(5) 0.0679(9) 0.050(2) -0.0167(8) -0.031(2)
C13 0.113(7) 0.125(8) 0.089(6) 0.010(5) -0.038(5) -0.007(6)
C14 0.176(13) 0.180(13) 0.245(15) -0.077(12) -0.058(11) -0.003(11)
S1' 0.0968(12) 0.203(5) 0.0679(9) 0.050(2) -0.0167(8) -0.031(2)
C13' 0.117(19) 0.13(2) 0.042(9) -0.001(10) -0.009(10) -0.010(16)
C14' 0.18(2) 0.136(19) 0.18(2) 0.036(17) -0.030(17) -0.020(17)
O1 0.0303(13) 0.0912(19) 0.0885(19) -0.0091(16) 0.0043(11) -0.0047(13)
O2 0.0384(17) 0.203(5) 0.130(3) 0.021(3) -0.0089(19) -0.009(2)
O3 0.0354(12) 0.0716(17) 0.0659(16) 0.0008(12) 0.0146(10) -0.0042(12)
C1 0.0363(18) 0.059(2) 0.056(2) -0.0052(17) 0.0040(14) -0.0047(16)
C2 0.041(2) 0.065(3) 0.099(3) 0.017(2) 0.002(2) -0.0117(18)
C3 0.0423(19) 0.054(2) 0.077(3) 0.009(2) -0.0007(17) 0.0084(17)
C4 0.0362(17) 0.067(2) 0.0508(19) 0.0016(16) 0.0012(14) -0.0030(16)
C5 0.060(2) 0.067(3) 0.063(2) -0.0193(19) 0.0023(18) 0.003(2)
C6 0.056(2) 0.062(2) 0.076(3) -0.006(2) 0.0046(19) 0.018(2)
C7 0.045(2) 0.059(2) 0.070(2) 0.0005(19) -0.0030(17) 0.0083(17)
C8 0.0273(15) 0.051(2) 0.0571(19) 0.0037(16) 0.0065(13) 0.0027(13)
C9 0.0335(16) 0.052(2) 0.0488(17) -0.0012(15) 0.0019(13) 0.0036(14)
C10 0.046(2) 0.087(3) 0.061(2) -0.005(2) -0.0057(16) -0.007(2)
C11 0.060(3) 0.116(4) 0.059(2) 0.011(3) -0.0075(18) -0.010(3)
C12 0.076(3) 0.116(4) 0.065(3) 0.012(3) 0.009(2) -0.010(3)
C15 0.058(2) 0.069(2) 0.057(2) -0.0042(18) 0.0015(16) -0.0035(19)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C12 1.776(6) . ?
S1 C13 1.808(9) . ?
C13 C14 1.490(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
S1' C12 1.773(13) . ?
S1' C13' 1.787(16) . ?
C13' C14' 1.468(19) . ?
C13' H13C 0.9700 . ?
C13' H13D 0.9700 . ?
C14' H14D 0.9600 . ?
C14' H14E 0.9600 . ?
C14' H14F 0.9600 . ?
O1 C1 1.220(4) . ?
O2 C12 1.119(6) . ?
O3 C8 1.420(4) . ?
O3 H3O 0.8259 . ?
C1 C9 1.502(5) . ?
C1 C2 1.505(6) . ?
C2 C3 1.519(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.542(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C10 1.498(5) . ?
C4 C5 1.536(6) . ?
C4 C8 1.549(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.502(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.505(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C9 1.523(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.556(4) . ?
C9 C15 1.545(5) . ?
C10 C11 1.289(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.504(6) . ?
C11 H11 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C13 98.6(4) . . ?
C14 C13 S1 114.0(9) . . ?
C14 C13 H13A 108.8 . . ?
S1 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
S1 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C12 S1' C13' 103.9(9) . . ?
C14' C13' S1' 118(2) . . ?
C14' C13' H13C 107.8 . . ?
S1' C13' H13C 107.8 . . ?
C14' C13' H13D 107.8 . . ?
S1' C13' H13D 107.8 . . ?
H13C C13' H13D 107.2 . . ?
C13' C14' H14D 109.5 . . ?
C13' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C13' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C8 O3 H3O 125.4 . . ?
O1 C1 C9 126.3(4) . . ?
O1 C1 C2 123.2(4) . . ?
C9 C1 C2 110.5(3) . . ?
C1 C2 C3 104.8(3) . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C2 C3 C8 104.8(3) . . ?
C2 C3 H3A 110.8 . . ?
C8 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C8 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C10 C4 C5 111.6(3) . . ?
C10 C4 C8 111.1(3) . . ?
C5 C4 C8 111.0(3) . . ?
C10 C4 H4 107.6 . . ?
C5 C4 H4 107.6 . . ?
C8 C4 H4 107.6 . . ?
C6 C5 C4 110.0(3) . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C5 C6 C7 111.1(3) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C9 115.2(3) . . ?
C6 C7 H7A 108.5 . . ?
C9 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
C9 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
O3 C8 C3 113.7(3) . . ?
O3 C8 C4 110.3(3) . . ?
C3 C8 C4 110.4(3) . . ?
O3 C8 C9 108.7(3) . . ?
C3 C8 C9 102.7(3) . . ?
C4 C8 C9 110.6(2) . . ?
C1 C9 C7 115.6(3) . . ?
C1 C9 C15 104.9(3) . . ?
C7 C9 C15 109.5(3) . . ?
C1 C9 C8 101.3(3) . . ?
C7 C9 C8 113.9(3) . . ?
C15 C9 C8 111.1(3) . . ?
C11 C10 C4 128.0(4) . . ?
C11 C10 H10 116.0 . . ?
C4 C10 H10 116.0 . . ?
C10 C11 C12 122.1(4) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
O2 C12 C11 127.1(5) . . ?
O2 C12 S1' 120.6(6) . . ?
C11 C12 S1' 107.9(5) . . ?
O2 C12 S1 122.3(5) . . ?
C11 C12 S1 110.6(4) . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3O O1 0.83 2.10 2.851(4) 151.8 1_455
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 25.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.393
_refine_diff_density_min -0.280
_refine_diff_density_rms 0.048
#==============================================================================
# start Validation Reply Form
_vrf_PLAT220_PC-O2-123-1_2-shelxl
;
PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.5 Ratio
RESPONSE: The data was collected at ambient temperature of 23 degree Celsius.
The thio ethyl group is showing positional disorder.
;
_vrf_PLAT230_PC-O2-123-1_2-shelxl
;
PROBLEM: Hirshfeld Test Diff for C11 -- C12 .. 7.0 su
RESPONSE: Atom C12 is connected to the thio ethyl ester group which shows
positional disorder.
;
_vrf_PLAT242_PC-O2-123-1_2-shelxl
;
PROBLEM: Check Low Ueq as Compared to Neighbors for C12
RESPONSE: Atom C12 is connected to the thio ethyl ester group which shows
positional disorder.
;
_vrf_PLAT340_PC-O2-123-1_2-shelxl
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.0052 Ang
RESPONSE: The data was collected at ambient temperature of 23 degree Celsius,
as a result, the thermal parameters of the atoms would be larger and thus
the bond precision lower.
;
#============================================================================
data_PC-O2-145-C-shelxl
_database_code_depnum_ccdc_archive 'CCDC 851778'
#TrackingRef '7922_web_deposit_cif_file_0_JunOU_1320126174.PC-O2-145-C-shelxl.cif'
# PC-O2-145-C Ou Jun_28-Jun-2011
_iucr_refine_instructions_details
;
TITL PC-O2-145-C_OuJun_21-Oct-2011
CELL 0.71073 8.64950 8.68690 13.44010 72.062 89.472 85.803
ZERR 2 0.00060 0.00060 0.00090 0.004 0.004 0.005
LATT -1
SFAC C H O S
UNIT 44 44 6 2
SHEL 8.000000 0.84
L.S. 10
FMAP 2
PLAN -20
TWIN
BOND $H
HTAB
HTAB O3 O1
HTAB O3 O4
HTAB O6 O4
TEMP 23.0
ACTA
SIZE 0.160 0.340 0.760
LIST 4
WGHT 0.145200 0.210400
BASF 0.09919
FVAR 1.11385
S1 4 0.767474 0.304287 0.823381 11.00000 0.06275 0.06652 =
0.09677 -0.03134 -0.02999 0.00425
S2 4 0.621256 0.428793 0.303287 11.00000 0.05637 0.09389 =
0.11687 -0.07420 0.00625 -0.01325
O1 3 0.573110 0.477888 0.676867 11.00000 0.07219 0.06691 =
0.06608 0.01092 -0.01832 -0.02465
O2 3 0.213930 -0.134474 0.874436 11.00000 0.10168 0.04930 =
0.08205 -0.00790 0.01135 -0.02568
O3 3 0.325759 0.352091 0.614987 11.00000 0.06069 0.07134 =
0.03995 0.00690 -0.00891 -0.01699
AFIX 1
H3O 2 0.419200 0.397800 0.615500 11.00000 -1.20000
AFIX 0
O4 3 0.516574 0.556913 0.445731 11.00000 0.08582 0.08322 =
0.05969 -0.03132 0.03556 -0.04267
O5 3 1.039319 0.997217 0.239629 11.00000 0.06002 0.08173 =
0.07900 -0.02371 0.02528 -0.03250
O6 3 0.674117 0.781591 0.500512 11.00000 0.07082 0.07232 =
0.04653 -0.03030 0.02197 -0.02828
AFIX 1
H6O 2 0.593200 0.735800 0.494800 11.00000 -1.20000
AFIX 0
C1 1 0.234258 0.009101 0.829616 11.00000 0.04784 0.04474 =
0.05073 -0.00363 0.00188 -0.01696
C2 1 0.222772 0.141287 0.875116 11.00000 0.03625 0.05330 =
0.04161 -0.00873 0.00474 -0.00718
C3 1 0.157616 0.148401 0.970474 11.00000 0.05708 0.07925 =
0.04675 -0.00922 0.00721 -0.00515
AFIX 43
H3 2 0.117618 0.057463 1.016843 11.00000 -1.20000
AFIX 0
C4 1 0.154457 0.289206 0.993033 11.00000 0.06620 0.09876 =
0.05644 -0.03161 0.00130 0.00886
AFIX 43
H4 2 0.112380 0.294375 1.055952 11.00000 -1.20000
AFIX 0
C5 1 0.211535 0.424795 0.925793 11.00000 0.06591 0.07937 =
0.08253 -0.04866 -0.00927 0.01052
AFIX 43
H5 2 0.208495 0.519817 0.944137 11.00000 -1.20000
AFIX 0
C6 1 0.274348 0.423004 0.829996 11.00000 0.04370 0.04594 =
0.07340 -0.02065 0.00246 0.00315
AFIX 43
H6 2 0.310835 0.516156 0.783729 11.00000 -1.20000
AFIX 0
C7 1 0.280908 0.277909 0.805562 11.00000 0.03316 0.04742 =
0.04566 -0.01177 0.00029 -0.00340
C8 1 0.528360 0.193754 0.738988 11.00000 0.04211 0.05374 =
0.03553 -0.01086 0.00372 -0.00447
AFIX 13
H8 2 0.538787 0.120779 0.810921 11.00000 -1.20000
AFIX 0
C9 1 0.605424 0.103596 0.666688 11.00000 0.05788 0.08465 =
0.06015 -0.03328 0.00366 0.00020
AFIX 23
H9A 2 0.590188 0.168803 0.594107 11.00000 -1.20000
H9B 2 0.715961 0.083959 0.681342 11.00000 -1.20000
AFIX 0
C10 1 0.532084 -0.056338 0.686238 11.00000 0.08645 0.08006 =
0.08482 -0.05125 0.00888 0.00698
AFIX 23
H10A 2 0.581384 -0.115480 0.642489 11.00000 -1.20000
H10B 2 0.549964 -0.121222 0.758650 11.00000 -1.20000
AFIX 0
C11 1 0.362547 -0.032665 0.663708 11.00000 0.08341 0.06985 =
0.06341 -0.03660 -0.00334 -0.01344
AFIX 23
H11A 2 0.320014 -0.137959 0.687214 11.00000 -1.20000
H11B 2 0.347218 0.009153 0.588484 11.00000 -1.20000
AFIX 0
C12 1 0.355167 0.233283 0.713850 11.00000 0.04931 0.04161 =
0.03566 -0.00688 0.00028 -0.00367
C13 1 0.269647 0.080406 0.712956 11.00000 0.06179 0.05268 =
0.04949 -0.02140 0.00454 -0.01964
C14 1 0.609354 0.344593 0.733842 11.00000 0.05405 0.06038 =
0.03922 -0.01071 0.00662 -0.01283
C15 1 0.829682 0.507471 0.794279 11.00000 0.05768 0.09177 =
0.08328 -0.03715 0.00533 -0.02637
AFIX 23
H15A 2 0.942108 0.500569 0.793654 11.00000 -1.20000
H15B 2 0.793759 0.568835 0.724143 11.00000 -1.20000
AFIX 0
C16 1 0.777845 0.600526 0.865483 11.00000 0.05278 0.05778 =
0.06031 -0.01214 -0.00984 -0.01032
C17 1 0.638196 0.573620 0.921450 11.00000 0.08239 0.07997 =
0.07168 -0.02630 0.01138 -0.02017
AFIX 43
H17 2 0.580295 0.489624 0.917365 11.00000 -1.20000
AFIX 0
C18 1 0.586510 0.666623 0.980739 11.00000 0.10427 0.11166 =
0.07396 -0.03281 0.00359 0.01305
AFIX 43
H18 2 0.495521 0.645342 1.018301 11.00000 -1.20000
AFIX 0
C19 1 0.671861 0.795610 0.984876 11.00000 0.14243 0.09657 =
0.10496 -0.04991 -0.03172 0.02162
AFIX 43
H19 2 0.635227 0.862982 1.023261 11.00000 -1.20000
AFIX 0
C20 1 0.809326 0.823160 0.932577 11.00000 0.13090 0.05936 =
0.11744 -0.03190 -0.04894 -0.00285
AFIX 43
H20 2 0.867068 0.906633 0.937764 11.00000 -1.20000
AFIX 0
C21 1 0.861495 0.728666 0.873091 11.00000 0.07426 0.06607 =
0.08744 -0.01296 -0.02616 -0.01293
AFIX 43
H21 2 0.953834 0.749578 0.837098 11.00000 -1.20000
AFIX 0
C22 1 0.110835 0.128863 0.659383 11.00000 0.06099 0.09143 =
0.06860 -0.03005 -0.00436 -0.02164
AFIX 137
H22A 2 0.052462 0.199774 0.690687 11.00000 -1.20000
H22B 2 0.056396 0.033433 0.667434 11.00000 -1.20000
H22C 2 0.123757 0.183861 0.586330 11.00000 -1.20000
AFIX 0
C23 1 0.919571 0.963125 0.284380 11.00000 0.05269 0.04276 =
0.05444 -0.01723 0.01053 -0.01672
C24 1 0.763057 0.998510 0.238252 11.00000 0.05432 0.04040 =
0.05094 -0.01489 0.00834 -0.00827
C25 1 0.709056 1.105932 0.143429 11.00000 0.09040 0.05196 =
0.05729 -0.01280 0.01236 -0.01451
AFIX 43
H25 2 0.777645 1.165538 0.095701 11.00000 -1.20000
AFIX 0
C26 1 0.550654 1.123191 0.120770 11.00000 0.08112 0.06540 =
0.06774 -0.01047 -0.02169 0.00161
AFIX 43
H26 2 0.514484 1.194118 0.056924 11.00000 -1.20000
AFIX 0
C27 1 0.445862 1.037541 0.190800 11.00000 0.06142 0.06404 =
0.07905 -0.02716 -0.01187 0.00700
AFIX 43
H27 2 0.340401 1.051006 0.174721 11.00000 -1.20000
AFIX 0
C28 1 0.501845 0.929758 0.286734 11.00000 0.04713 0.04796 =
0.07373 -0.02342 -0.00374 0.00348
AFIX 43
H28 2 0.432858 0.871723 0.334880 11.00000 -1.20000
AFIX 0
C29 1 0.656718 0.909740 0.309664 11.00000 0.04838 0.03603 =
0.04499 -0.01422 0.00477 -0.00795
C30 1 0.777383 0.627762 0.385887 11.00000 0.04771 0.04275 =
0.03725 -0.01087 0.00369 -0.00805
AFIX 13
H30 2 0.817892 0.648700 0.314983 11.00000 -1.20000
AFIX 0
C31 1 0.899416 0.516817 0.460153 11.00000 0.08159 0.04546 =
0.06606 -0.01160 -0.00744 0.00729
AFIX 23
H31A 2 0.910494 0.412112 0.448061 11.00000 -1.20000
H31B 2 0.868675 0.500219 0.532074 11.00000 -1.20000
AFIX 0
C32 1 1.053823 0.597461 0.440104 11.00000 0.06543 0.07054 =
0.09530 -0.02508 -0.01819 0.01509
AFIX 23
H32A 2 1.133247 0.528327 0.486719 11.00000 -1.20000
H32B 2 1.085392 0.609983 0.368768 11.00000 -1.20000
AFIX 0
C33 1 1.039096 0.762864 0.457591 11.00000 0.05428 0.09065 =
0.07826 -0.02415 -0.00520 -0.01290
AFIX 23
H33A 2 1.029415 0.746849 0.531997 11.00000 -1.20000
H33B 2 1.133935 0.815831 0.435121 11.00000 -1.20000
AFIX 0
C34 1 0.745691 0.794275 0.404156 11.00000 0.04238 0.04232 =
0.03481 -0.01383 0.00508 -0.00678
C35 1 0.902846 0.875441 0.400946 11.00000 0.05218 0.05473 =
0.05056 -0.01920 -0.00384 -0.02050
C36 1 0.628026 0.545015 0.388936 11.00000 0.05473 0.03949 =
0.04745 -0.00788 0.00233 -0.00565
C37 1 0.440094 0.336528 0.341343 11.00000 0.06480 0.04547 =
0.09404 -0.02561 -0.00624 -0.00953
AFIX 23
H37A 2 0.453726 0.224086 0.342651 11.00000 -1.20000
H37B 2 0.417225 0.337132 0.412019 11.00000 -1.20000
AFIX 0
C38 1 0.302756 0.416130 0.272421 11.00000 0.05896 0.04854 =
0.06144 -0.02425 0.00442 -0.00942
C39 1 0.290731 0.575341 0.206297 11.00000 0.09245 0.05108 =
0.07560 0.00139 0.01502 -0.00696
AFIX 43
H39 2 0.374153 0.639607 0.198539 11.00000 -1.20000
AFIX 0
C40 1 0.149375 0.638425 0.150801 11.00000 0.15040 0.06977 =
0.06452 0.00381 0.02308 0.02732
AFIX 43
H40 2 0.140351 0.744396 0.106012 11.00000 -1.20000
AFIX 0
C41 1 0.027367 0.544679 0.162862 11.00000 0.07132 0.10862 =
0.06856 -0.03037 -0.00187 0.00674
AFIX 43
H41 2 -0.064468 0.586304 0.125729 11.00000 -1.20000
AFIX 0
C42 1 0.038874 0.391778 0.228348 11.00000 0.05421 0.08438 =
0.08087 -0.04154 0.00365 -0.00639
AFIX 43
H42 2 -0.046331 0.329631 0.237880 11.00000 -1.20000
AFIX 0
C43 1 0.171739 0.328257 0.279901 11.00000 0.06513 0.05885 =
0.07053 -0.02568 0.00186 -0.00470
AFIX 43
H43 2 0.177130 0.220946 0.322572 11.00000 -1.20000
AFIX 0
C44 1 0.880397 1.013859 0.451118 11.00000 0.10028 0.07118 =
0.06181 -0.03453 0.00984 -0.03685
AFIX 137
H44A 2 0.792580 1.085522 0.419080 11.00000 -1.20000
H44B 2 0.971574 1.073347 0.440654 11.00000 -1.20000
H44C 2 0.863130 0.968463 0.524704 11.00000 -1.20000
HKLF 4
REM PC-O2-145-C_OuJun_21-Oct-2011
REM R1 = 0.0709 for 4860 Fo > 4sig(Fo) and 0.0852 for all 5970 data
REM 472 parameters refined using 3 restraints
END
WGHT 0.1444 0.2152
REM Highest difference peak 0.419, deepest hole -0.320, 1-sigma level 0.071
Q1 1 1.0238 0.5879 0.5136 11.00000 0.05 0.42
Q2 1 0.5769 0.5373 0.2808 11.00000 0.05 0.41
Q3 1 0.6111 0.4760 0.4759 11.00000 0.05 0.40
Q4 1 0.6499 0.3313 0.8129 11.00000 0.05 0.33
Q5 1 0.7265 0.3612 0.3461 11.00000 0.05 0.29
Q6 1 0.8203 0.1900 0.8578 11.00000 0.05 0.27
Q7 1 0.1736 0.6003 0.1597 11.00000 0.05 0.27
Q8 1 0.1870 0.5077 1.0146 11.00000 0.05 0.27
Q9 1 0.8690 0.5959 0.8958 11.00000 0.05 0.26
Q10 1 0.3566 0.4234 0.2900 11.00000 0.05 0.26
Q11 1 0.7232 0.7595 0.3851 11.00000 0.05 0.26
Q12 1 0.6516 0.5926 0.3909 11.00000 0.05 0.25
Q13 1 0.1150 0.4507 0.1975 11.00000 0.05 0.25
Q14 1 0.7423 0.4493 0.5956 11.00000 0.05 0.24
Q15 1 0.4058 0.3890 0.0261 11.00000 0.05 0.24
Q16 1 0.1902 0.1380 0.8982 11.00000 0.05 0.24
Q17 1 0.6759 0.9480 0.2900 11.00000 0.05 0.23
Q18 1 0.9520 0.4276 0.8419 11.00000 0.05 0.23
Q19 1 0.4089 -0.0780 0.7260 11.00000 0.05 0.23
Q20 1 0.6926 0.6739 1.0114 11.00000 0.05 0.23
;
_audit_creation_method SHELXL-97
_chemical_absolute_configuration rmad
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C22 H22 O3 S'
_chemical_formula_sum 'C22 H22 O3 S'
_chemical_formula_weight 366.46
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P 1'
_symmetry_space_group_name_Hall 'P 1'
_symmetry_Int_Tables_number 1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
_cell_length_a 8.6495(6)
_cell_length_b 8.6869(6)
_cell_length_c 13.4401(9)
_cell_angle_alpha 72.062(4)
_cell_angle_beta 89.472(4)
_cell_angle_gamma 85.803(5)
_cell_volume 958.09(11)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 13175
_cell_measurement_theta_min 2.83
_cell_measurement_theta_max 25.03
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.76
_exptl_crystal_size_mid 0.34
_exptl_crystal_size_min 0.16
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.270
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 388
_exptl_absorpt_coefficient_mu 0.187
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.8709
_exptl_absorpt_correction_T_max 0.9707
_exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX CCD'
_diffrn_measurement_method '\w & \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 13175
_diffrn_reflns_av_R_equivalents 0.0479
_diffrn_reflns_av_sigmaI/netI 0.0717
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.83
_diffrn_reflns_theta_max 25.03
_reflns_number_total 5970
_reflns_number_gt 4860
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'APEX (Bruker AXS Inc, 2007)'
_computing_cell_refinement 'SAINT v7.34A (Bruker AXS Inc, 2007)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2006)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'MERCURY (Macrae et al., 2008)'
_computing_publication_material 'SHELXL97 (Sheldrick, 2008)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
The structure was solved by direct methods (SHELXS-97) and expanded
using Fourier techniques. All non-H atoms were refined anisotropically.
All of the C-bound H atoms were observable from difference Fourier map but were
all placed at geometrical positions with C---H = 0.93, 0.96, 0.97 and 0.98\%A
for phenyl, methyl, methylene and methine H-atoms respectively. All C-bound
H-atoms were refined using riding model with U~iso~(H) =
1.2U~eq~(Carrier). The O-bound hydrogen atoms were located from
difference Fourier map and also refined using riding model of
U~iso~(H) = 1.2U~eq~(Carrier).
Floating origin restraints (three) were used.
Highest peak is 0.42 at (0.0238, 0.5878, 0.5136) [1.00\%A from C32]
Deepest hole is -0.32 at (0.0916, 0.1768, 0.7216) [0.52\%A from H22A]
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1452P)^2^+0.2104P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack (1983), 2596 Friedel pairs'
_refine_ls_abs_structure_Flack 0.10(14)
_refine_ls_number_reflns 5970
_refine_ls_number_parameters 472
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.0852
_refine_ls_R_factor_gt 0.0709
_refine_ls_wR_factor_ref 0.2362
_refine_ls_wR_factor_gt 0.2023
_refine_ls_goodness_of_fit_ref 1.107
_refine_ls_restrained_S_all 1.106
_refine_ls_shift/su_max 0.005
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.76747(18) 0.30429(18) 0.82338(15) 0.0742(5) Uani 1 1 d . . .
S2 S 0.62126(18) 0.4288(2) 0.30329(16) 0.0792(6) Uani 1 1 d . . .
O1 O 0.5731(5) 0.4779(5) 0.6769(3) 0.0744(13) Uani 1 1 d . . .
O2 O 0.2139(6) -0.1345(5) 0.8744(4) 0.0795(13) Uani 1 1 d . . .
O3 O 0.3258(5) 0.3521(5) 0.6150(3) 0.0621(10) Uani 1 1 d . . .
H3O H 0.4192 0.3978 0.6155 0.075 Uiso 1 1 d . . .
O4 O 0.5166(6) 0.5569(6) 0.4457(3) 0.0725(12) Uani 1 1 d . . .
O5 O 1.0393(5) 0.9972(6) 0.2396(4) 0.0726(12) Uani 1 1 d . . .
O6 O 0.6741(5) 0.7816(5) 0.5005(3) 0.0594(10) Uani 1 1 d . . .
H6O H 0.5932 0.7358 0.4948 0.071 Uiso 1 1 d . . .
C1 C 0.2343(6) 0.0091(6) 0.8296(4) 0.0496(11) Uani 1 1 d . . .
C2 C 0.2228(5) 0.1413(6) 0.8751(4) 0.0449(10) Uani 1 1 d . . .
C3 C 0.1576(7) 0.1484(8) 0.9705(4) 0.0634(15) Uani 1 1 d . . .
H3 H 0.1176 0.0575 1.0168 0.076 Uiso 1 1 calc R . .
C4 C 0.1545(8) 0.2892(10) 0.9930(5) 0.0728(17) Uani 1 1 d . . .
H4 H 0.1124 0.2944 1.0560 0.087 Uiso 1 1 calc R . .
C5 C 0.2115(8) 0.4248(9) 0.9258(6) 0.0713(17) Uani 1 1 d . . .
H5 H 0.2085 0.5198 0.9441 0.086 Uiso 1 1 calc R . .
C6 C 0.2743(6) 0.4230(6) 0.8300(5) 0.0542(12) Uani 1 1 d . . .
H6 H 0.3108 0.5162 0.7837 0.065 Uiso 1 1 calc R . .
C7 C 0.2809(5) 0.2779(6) 0.8056(4) 0.0426(10) Uani 1 1 d . . .
C8 C 0.5284(5) 0.1938(6) 0.7390(4) 0.0444(10) Uani 1 1 d . . .
H8 H 0.5388 0.1208 0.8109 0.053 Uiso 1 1 calc R . .
C9 C 0.6054(7) 0.1036(8) 0.6667(5) 0.0654(15) Uani 1 1 d . . .
H9A H 0.5902 0.1688 0.5941 0.078 Uiso 1 1 calc R . .
H9B H 0.7160 0.0840 0.6813 0.078 Uiso 1 1 calc R . .
C10 C 0.5321(9) -0.0563(9) 0.6862(6) 0.0786(19) Uani 1 1 d . . .
H10A H 0.5814 -0.1155 0.6425 0.094 Uiso 1 1 calc R . .
H10B H 0.5500 -0.1212 0.7586 0.094 Uiso 1 1 calc R . .
C11 C 0.3625(8) -0.0327(8) 0.6637(5) 0.0681(16) Uani 1 1 d . . .
H11A H 0.3200 -0.1380 0.6872 0.082 Uiso 1 1 calc R . .
H11B H 0.3472 0.0092 0.5885 0.082 Uiso 1 1 calc R . .
C12 C 0.3552(6) 0.2333(6) 0.7139(3) 0.0433(10) Uani 1 1 d . . .
C13 C 0.2696(7) 0.0804(6) 0.7130(4) 0.0526(12) Uani 1 1 d . . .
C14 C 0.6094(6) 0.3446(7) 0.7338(4) 0.0519(12) Uani 1 1 d . . .
C15 C 0.8297(8) 0.5075(9) 0.7943(6) 0.0742(18) Uani 1 1 d . . .
H15A H 0.9421 0.5006 0.7937 0.089 Uiso 1 1 calc R . .
H15B H 0.7938 0.5688 0.7241 0.089 Uiso 1 1 calc R . .
C16 C 0.7778(7) 0.6005(7) 0.8655(5) 0.0579(13) Uani 1 1 d . . .
C17 C 0.6382(9) 0.5736(9) 0.9214(6) 0.0767(18) Uani 1 1 d . . .
H17 H 0.5803 0.4896 0.9174 0.092 Uiso 1 1 calc R . .
C18 C 0.5865(12) 0.6666(12) 0.9807(6) 0.097(2) Uani 1 1 d . . .
H18 H 0.4955 0.6453 1.0183 0.116 Uiso 1 1 calc R . .
C19 C 0.6719(16) 0.7956(13) 0.9849(9) 0.112(3) Uani 1 1 d . . .
H19 H 0.6352 0.8630 1.0233 0.134 Uiso 1 1 calc R . .
C20 C 0.8093(14) 0.8232(9) 0.9326(8) 0.101(3) Uani 1 1 d . . .
H20 H 0.8671 0.9066 0.9378 0.122 Uiso 1 1 calc R . .
C21 C 0.8615(9) 0.7287(8) 0.8731(6) 0.0778(19) Uani 1 1 d . . .
H21 H 0.9538 0.7496 0.8371 0.093 Uiso 1 1 calc R . .
C22 C 0.1108(8) 0.1289(9) 0.6594(6) 0.0716(16) Uani 1 1 d . . .
H22A H 0.0525 0.1998 0.6907 0.086 Uiso 1 1 calc R . .
H22B H 0.0564 0.0334 0.6674 0.086 Uiso 1 1 calc R . .
H22C H 0.1238 0.1839 0.5863 0.086 Uiso 1 1 calc R . .
C23 C 0.9196(6) 0.9631(6) 0.2844(4) 0.0488(11) Uani 1 1 d . . .
C24 C 0.7631(6) 0.9985(6) 0.2383(4) 0.0482(11) Uani 1 1 d . . .
C25 C 0.7091(9) 1.1059(7) 0.1434(5) 0.0671(16) Uani 1 1 d . . .
H25 H 0.7776 1.1655 0.0957 0.080 Uiso 1 1 calc R . .
C26 C 0.5507(9) 1.1232(8) 0.1208(6) 0.0739(18) Uani 1 1 d . . .
H26 H 0.5145 1.1941 0.0569 0.089 Uiso 1 1 calc R . .
C27 C 0.4459(8) 1.0375(8) 0.1908(6) 0.0675(15) Uani 1 1 d . . .
H27 H 0.3404 1.0510 0.1747 0.081 Uiso 1 1 calc R . .
C28 C 0.5018(6) 0.9298(6) 0.2867(5) 0.0555(13) Uani 1 1 d . . .
H28 H 0.4329 0.8717 0.3349 0.067 Uiso 1 1 calc R . .
C29 C 0.6567(5) 0.9097(5) 0.3097(4) 0.0425(10) Uani 1 1 d . . .
C30 C 0.7774(5) 0.6278(5) 0.3859(4) 0.0427(10) Uani 1 1 d . . .
H30 H 0.8179 0.6487 0.3150 0.051 Uiso 1 1 calc R . .
C31 C 0.8994(8) 0.5168(7) 0.4602(5) 0.0662(15) Uani 1 1 d . . .
H31A H 0.9105 0.4121 0.4481 0.079 Uiso 1 1 calc R . .
H31B H 0.8687 0.5002 0.5321 0.079 Uiso 1 1 calc R . .
C32 C 1.0538(8) 0.5975(8) 0.4401(7) 0.0781(18) Uani 1 1 d . . .
H32A H 1.1332 0.5283 0.4867 0.094 Uiso 1 1 calc R . .
H32B H 1.0854 0.6100 0.3688 0.094 Uiso 1 1 calc R . .
C33 C 1.0391(8) 0.7629(9) 0.4576(6) 0.0744(17) Uani 1 1 d . . .
H33A H 1.0294 0.7468 0.5320 0.089 Uiso 1 1 calc R . .
H33B H 1.1339 0.8158 0.4351 0.089 Uiso 1 1 calc R . .
C34 C 0.7457(5) 0.7943(5) 0.4042(3) 0.0392(9) Uani 1 1 d . . .
C35 C 0.9028(6) 0.8754(6) 0.4009(4) 0.0509(12) Uani 1 1 d . . .
C36 C 0.6280(6) 0.5450(6) 0.3889(4) 0.0484(11) Uani 1 1 d . . .
C37 C 0.4401(7) 0.3365(7) 0.3413(6) 0.0668(15) Uani 1 1 d . . .
H37A H 0.4537 0.2241 0.3427 0.080 Uiso 1 1 calc R . .
H37B H 0.4172 0.3371 0.4120 0.080 Uiso 1 1 calc R . .
C38 C 0.3028(7) 0.4161(6) 0.2724(5) 0.0544(12) Uani 1 1 d . . .
C39 C 0.2907(10) 0.5753(8) 0.2063(6) 0.0778(19) Uani 1 1 d . . .
H39 H 0.3742 0.6396 0.1985 0.093 Uiso 1 1 calc R . .
C40 C 0.1494(13) 0.6384(10) 0.1508(6) 0.102(3) Uani 1 1 d . . .
H40 H 0.1404 0.7444 0.1060 0.123 Uiso 1 1 calc R . .
C41 C 0.0274(9) 0.5447(11) 0.1629(6) 0.083(2) Uani 1 1 d . . .
H41 H -0.0645 0.5863 0.1257 0.099 Uiso 1 1 calc R . .
C42 C 0.0389(7) 0.3918(9) 0.2283(6) 0.0694(16) Uani 1 1 d . . .
H42 H -0.0463 0.3296 0.2379 0.083 Uiso 1 1 calc R . .
C43 C 0.1717(8) 0.3283(8) 0.2799(5) 0.0635(14) Uani 1 1 d . . .
H43 H 0.1771 0.2209 0.3226 0.076 Uiso 1 1 calc R . .
C44 C 0.8804(9) 1.0139(8) 0.4511(5) 0.0730(18) Uani 1 1 d . . .
H44A H 0.7926 1.0855 0.4191 0.088 Uiso 1 1 calc R . .
H44B H 0.9716 1.0733 0.4407 0.088 Uiso 1 1 calc R . .
H44C H 0.8631 0.9685 0.5247 0.088 Uiso 1 1 calc 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
S1 0.0628(9) 0.0665(9) 0.0968(12) -0.0313(8) -0.0300(8) 0.0042(7)
S2 0.0564(9) 0.0939(12) 0.1169(15) -0.0742(11) 0.0062(9) -0.0133(8)
O1 0.072(3) 0.067(3) 0.066(2) 0.011(2) -0.018(2) -0.025(2)
O2 0.102(4) 0.049(2) 0.082(3) -0.008(2) 0.011(3) -0.026(2)
O3 0.061(2) 0.071(2) 0.0399(19) 0.0069(17) -0.0089(16) -0.0170(18)
O4 0.086(3) 0.083(3) 0.060(2) -0.031(2) 0.036(2) -0.043(2)
O5 0.060(3) 0.082(3) 0.079(3) -0.024(2) 0.025(2) -0.032(2)
O6 0.071(2) 0.072(2) 0.0465(19) -0.0303(18) 0.0220(17) -0.0283(19)
C1 0.048(3) 0.045(2) 0.051(3) -0.004(2) 0.002(2) -0.017(2)
C2 0.036(2) 0.053(3) 0.042(2) -0.009(2) 0.0047(18) -0.0072(19)
C3 0.057(3) 0.079(4) 0.047(3) -0.009(3) 0.007(2) -0.005(3)
C4 0.066(4) 0.099(5) 0.056(3) -0.032(3) 0.001(3) 0.009(3)
C5 0.066(4) 0.079(4) 0.083(4) -0.049(4) -0.009(3) 0.011(3)
C6 0.044(3) 0.046(3) 0.073(4) -0.021(2) 0.002(2) 0.003(2)
C7 0.033(2) 0.047(2) 0.046(2) -0.012(2) 0.0003(18) -0.0034(18)
C8 0.042(2) 0.054(3) 0.036(2) -0.011(2) 0.0037(18) -0.0045(19)
C9 0.058(3) 0.085(4) 0.060(3) -0.033(3) 0.004(3) 0.000(3)
C10 0.086(5) 0.080(4) 0.085(5) -0.051(4) 0.009(4) 0.007(3)
C11 0.083(4) 0.070(4) 0.063(3) -0.037(3) -0.003(3) -0.013(3)
C12 0.049(3) 0.042(2) 0.036(2) -0.0069(19) 0.0003(19) -0.0037(19)
C13 0.062(3) 0.053(3) 0.049(3) -0.021(2) 0.005(2) -0.020(2)
C14 0.054(3) 0.060(3) 0.039(2) -0.011(2) 0.007(2) -0.013(2)
C15 0.058(4) 0.092(5) 0.083(4) -0.037(4) 0.005(3) -0.026(3)
C16 0.053(3) 0.058(3) 0.060(3) -0.012(3) -0.010(2) -0.010(2)
C17 0.082(5) 0.080(4) 0.072(4) -0.026(4) 0.011(3) -0.020(3)
C18 0.104(6) 0.112(7) 0.074(5) -0.033(5) 0.004(4) 0.013(5)
C19 0.142(10) 0.097(6) 0.105(7) -0.050(5) -0.032(7) 0.022(6)
C20 0.131(8) 0.059(4) 0.117(7) -0.032(4) -0.049(6) -0.003(4)
C21 0.074(4) 0.066(4) 0.087(5) -0.013(3) -0.026(4) -0.013(3)
C22 0.061(4) 0.091(4) 0.069(4) -0.030(3) -0.004(3) -0.022(3)
C23 0.053(3) 0.043(2) 0.054(3) -0.017(2) 0.011(2) -0.017(2)
C24 0.054(3) 0.040(2) 0.051(3) -0.015(2) 0.008(2) -0.008(2)
C25 0.090(4) 0.052(3) 0.057(3) -0.013(3) 0.012(3) -0.015(3)
C26 0.081(4) 0.065(4) 0.068(4) -0.010(3) -0.022(3) 0.002(3)
C27 0.061(3) 0.064(3) 0.079(4) -0.027(3) -0.012(3) 0.007(3)
C28 0.047(3) 0.048(3) 0.074(4) -0.023(3) -0.004(2) 0.003(2)
C29 0.048(3) 0.036(2) 0.045(2) -0.0142(19) 0.0048(19) -0.0080(18)
C30 0.048(3) 0.043(2) 0.037(2) -0.0109(19) 0.0037(19) -0.0081(19)
C31 0.082(4) 0.045(3) 0.066(4) -0.012(3) -0.007(3) 0.007(3)
C32 0.065(4) 0.071(4) 0.095(5) -0.025(4) -0.018(3) 0.015(3)
C33 0.054(4) 0.091(5) 0.078(4) -0.024(4) -0.005(3) -0.013(3)
C34 0.042(2) 0.042(2) 0.035(2) -0.0138(18) 0.0051(17) -0.0068(18)
C35 0.052(3) 0.055(3) 0.051(3) -0.019(2) -0.004(2) -0.021(2)
C36 0.055(3) 0.039(2) 0.047(3) -0.008(2) 0.002(2) -0.006(2)
C37 0.065(4) 0.045(3) 0.094(4) -0.026(3) -0.006(3) -0.010(2)
C38 0.059(3) 0.049(3) 0.061(3) -0.024(2) 0.004(2) -0.009(2)
C39 0.092(5) 0.051(3) 0.076(4) 0.001(3) 0.015(4) -0.007(3)
C40 0.150(9) 0.070(4) 0.065(4) 0.004(4) 0.023(5) 0.027(5)
C41 0.071(4) 0.109(6) 0.069(4) -0.030(4) -0.002(3) 0.007(4)
C42 0.054(3) 0.084(4) 0.081(4) -0.042(4) 0.004(3) -0.006(3)
C43 0.065(4) 0.059(3) 0.071(4) -0.026(3) 0.002(3) -0.005(3)
C44 0.100(5) 0.071(4) 0.062(3) -0.035(3) 0.010(3) -0.037(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C14 1.773(6) . ?
S1 C15 1.808(7) . ?
S2 C36 1.753(6) . ?
S2 C37 1.810(6) . ?
O1 C14 1.196(7) . ?
O2 C1 1.232(6) . ?
O3 C12 1.421(6) . ?
O3 H3O 0.9272 . ?
O4 C36 1.242(7) . ?
O5 C23 1.202(6) . ?
O6 C34 1.407(6) . ?
O6 H6O 0.8453 . ?
C1 C2 1.455(8) . ?
C1 C13 1.535(7) . ?
C2 C7 1.389(7) . ?
C2 C3 1.412(8) . ?
C3 C4 1.346(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(7) . ?
C6 H6 0.9300 . ?
C7 C12 1.525(7) . ?
C8 C14 1.513(7) . ?
C8 C12 1.529(7) . ?
C8 C9 1.543(8) . ?
C8 H8 0.9800 . ?
C9 C10 1.517(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.487(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C13 1.524(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.570(7) . ?
C13 C22 1.526(9) . ?
C15 C16 1.478(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C21 1.401(9) . ?
C16 C17 1.413(9) . ?
C17 C18 1.351(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.401(15) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(16) . ?
C19 H19 0.9300 . ?
C20 C21 1.364(14) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.466(8) . ?
C23 C35 1.527(7) . ?
C24 C25 1.388(9) . ?
C24 C29 1.412(7) . ?
C25 C26 1.394(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.383(10) . ?
C26 H26 0.9300 . ?
C27 C28 1.405(9) . ?
C27 H27 0.9300 . ?
C28 C29 1.364(7) . ?
C28 H28 0.9300 . ?
C29 C34 1.527(7) . ?
C30 C36 1.518(7) . ?
C30 C31 1.522(8) . ?
C30 C34 1.545(6) . ?
C30 H30 0.9800 . ?
C31 C32 1.537(10) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.522(11) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C35 1.521(9) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.571(6) . ?
C35 C44 1.550(8) . ?
C37 C38 1.501(9) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.392(8) . ?
C38 C43 1.398(9) . ?
C39 C40 1.421(14) . ?
C39 H39 0.9300 . ?
C40 C41 1.358(13) . ?
C40 H40 0.9300 . ?
C41 C42 1.346(11) . ?
C41 H41 0.9300 . ?
C42 C43 1.339(10) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 S1 C15 99.1(3) . . ?
C36 S2 C37 100.4(3) . . ?
C12 O3 H3O 93.4 . . ?
C34 O6 H6O 101.5 . . ?
O2 C1 C2 126.9(5) . . ?
O2 C1 C13 125.0(5) . . ?
C2 C1 C13 108.0(4) . . ?
C7 C2 C3 120.4(5) . . ?
C7 C2 C1 109.4(4) . . ?
C3 C2 C1 130.1(5) . . ?
C4 C3 C2 118.8(6) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 121.7(6) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 121.1(6) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 118.3(5) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C2 C7 C6 119.7(5) . . ?
C2 C7 C12 109.5(4) . . ?
C6 C7 C12 130.6(4) . . ?
C14 C8 C12 111.5(4) . . ?
C14 C8 C9 111.4(4) . . ?
C12 C8 C9 111.0(4) . . ?
C14 C8 H8 107.6 . . ?
C12 C8 H8 107.6 . . ?
C9 C8 H8 107.6 . . ?
C10 C9 C8 108.4(5) . . ?
C10 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C11 C10 C9 112.1(6) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 C13 116.4(5) . . ?
C10 C11 H11A 108.2 . . ?
C13 C11 H11A 108.2 . . ?
C10 C11 H11B 108.2 . . ?
C13 C11 H11B 108.2 . . ?
H11A C11 H11B 107.4 . . ?
O3 C12 C7 114.3(4) . . ?
O3 C12 C8 112.6(4) . . ?
C7 C12 C8 107.3(4) . . ?
O3 C12 C13 106.9(4) . . ?
C7 C12 C13 102.7(4) . . ?
C8 C12 C13 112.6(4) . . ?
C11 C13 C22 109.6(5) . . ?
C11 C13 C1 116.0(5) . . ?
C22 C13 C1 104.7(4) . . ?
C11 C13 C12 114.0(5) . . ?
C22 C13 C12 111.4(5) . . ?
C1 C13 C12 100.6(4) . . ?
O1 C14 C8 125.1(5) . . ?
O1 C14 S1 122.3(4) . . ?
C8 C14 S1 112.6(4) . . ?
C16 C15 S1 117.0(5) . . ?
C16 C15 H15A 108.0 . . ?
S1 C15 H15A 108.0 . . ?
C16 C15 H15B 108.0 . . ?
S1 C15 H15B 108.0 . . ?
H15A C15 H15B 107.3 . . ?
C21 C16 C17 117.5(7) . . ?
C21 C16 C15 120.1(6) . . ?
C17 C16 C15 122.2(5) . . ?
C18 C17 C16 121.8(7) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 119.1(10) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C20 C19 C18 120.4(9) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.3(8) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C16 120.9(8) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
C13 C22 H22A 109.5 . . ?
C13 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C13 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 C24 126.8(5) . . ?
O5 C23 C35 126.0(5) . . ?
C24 C23 C35 107.2(4) . . ?
C25 C24 C29 119.5(5) . . ?
C25 C24 C23 130.7(5) . . ?
C29 C24 C23 109.8(4) . . ?
C24 C25 C26 119.1(6) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C27 C26 C25 121.7(6) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C26 C27 C28 118.7(6) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C29 C28 C27 120.4(6) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C24 120.6(5) . . ?
C28 C29 C34 130.2(4) . . ?
C24 C29 C34 109.1(4) . . ?
C36 C30 C31 111.3(4) . . ?
C36 C30 C34 110.9(4) . . ?
C31 C30 C34 113.4(4) . . ?
C36 C30 H30 106.9 . . ?
C31 C30 H30 106.9 . . ?
C34 C30 H30 106.9 . . ?
C30 C31 C32 108.2(5) . . ?
C30 C31 H31A 110.1 . . ?
C32 C31 H31A 110.1 . . ?
C30 C31 H31B 110.1 . . ?
C32 C31 H31B 110.1 . . ?
H31A C31 H31B 108.4 . . ?
C33 C32 C31 111.1(6) . . ?
C33 C32 H32A 109.4 . . ?
C31 C32 H32A 109.4 . . ?
C33 C32 H32B 109.4 . . ?
C31 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
C35 C33 C32 114.9(5) . . ?
C35 C33 H33A 108.5 . . ?
C32 C33 H33A 108.5 . . ?
C35 C33 H33B 108.5 . . ?
C32 C33 H33B 108.5 . . ?
H33A C33 H33B 107.5 . . ?
O6 C34 C29 114.1(4) . . ?
O6 C34 C30 112.4(4) . . ?
C29 C34 C30 108.8(4) . . ?
O6 C34 C35 109.0(4) . . ?
C29 C34 C35 102.7(4) . . ?
C30 C34 C35 109.3(4) . . ?
C33 C35 C23 117.6(5) . . ?
C33 C35 C44 107.0(5) . . ?
C23 C35 C44 104.3(4) . . ?
C33 C35 C34 115.5(4) . . ?
C23 C35 C34 102.4(4) . . ?
C44 C35 C34 109.3(5) . . ?
O4 C36 C30 124.4(5) . . ?
O4 C36 S2 120.9(4) . . ?
C30 C36 S2 114.6(4) . . ?
C38 C37 S2 115.5(5) . . ?
C38 C37 H37A 108.4 . . ?
S2 C37 H37A 108.4 . . ?
C38 C37 H37B 108.4 . . ?
S2 C37 H37B 108.4 . . ?
H37A C37 H37B 107.5 . . ?
C39 C38 C43 116.7(6) . . ?
C39 C38 C37 125.2(6) . . ?
C43 C38 C37 117.9(5) . . ?
C38 C39 C40 119.1(7) . . ?
C38 C39 H39 120.4 . . ?
C40 C39 H39 120.4 . . ?
C41 C40 C39 120.3(7) . . ?
C41 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?
C42 C41 C40 120.2(7) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C43 C42 C41 120.7(7) . . ?
C43 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C42 C43 C38 122.9(6) . . ?
C42 C43 H43 118.6 . . ?
C38 C43 H43 118.6 . . ?
C35 C44 H44A 109.5 . . ?
C35 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C35 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3O O1 0.93 1.86 2.720(5) 153.9 .
O3 H3O O4 0.93 2.45 2.989(5) 116.8 .
O6 H6O O4 0.85 2.02 2.739(6) 142.5 .
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full 25.03
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max 0.419
_refine_diff_density_min -0.320
_refine_diff_density_rms 0.071
loop_
_publ_manuscript_incl_extra_item
C--H
CgJ
H...CgJ
C--H...CgJ
C...CgJ
loop_
_geom_extra_tableA_col_1
_geom_extra_tableA_col_2
_geom_extra_tableA_col_3
_geom_extra_tableA_col_4
_geom_extra_tableA_col_5
C--H CgJ H...CgJ C--H...CgJ C...CgJ
C10-H10B 2^i^ 2.71 155 3.616(9)
C15-H15A 1^ii^ 3.00 141 3.800(8)
C32-H32B 3^ii^ 2.67 151 3.545(9)
_geom_extra_table_head_A
;
Table 2. C--H...\p interactions (\%A, \%)
Cg1, Cg2 and Cg3 are centroids
of the rings C2-C7, C16-C21 and C38-C43 respectively,
H...CgJ and 'C...CgJ' are the distances between ring
centroid and the specified atom H and C respectively. C--H...CgJ
is the angle between the C--H bond and the ring centroid CgJ.
;
_geom_table_footnote_A
;
symmetry operators:
^i^: X, Y-1, Z
^ii^: 1+X, Y, Z
;
#==============================================================================
# start Validation Reply Form
_vrf_PLAT230_PC-O2-145-C-shelxl
;
PROBLEM: Hirshfeld Test Diff for C40 -- C41 .. 9.3 su
RESPONSE: This may be to slight wiggling motion of the phenyl rings. Since
it was not very serious and thus not treated as separate disordered
parts in refinement.
;
_vrf_PLAT234_PC-O2-145-C-shelxl
;
PROBLEM: Large Hirshfeld Difference C39 -- C40 .. 0.19 Ang.
RESPONSE: This may be to slight wiggling motion of the phenyl rings. Since
it was not very serious and thus not treated as separate disordered
parts in refinement.
;
_vrf_PLAT241_PC-O2-145-C-shelxl
;
PROBLEM: Check High Ueq as Compared to Neighbors for S2, C40
RESPONSE: This is due to the slight jiggle of the thio linkage. Since
it was not very serious and thus not treated as separate disordered
parts in refinement.
;
_vrf_PLAT242_PC-O2-145-C-shelxl
;
PROBLEM: Check Low Ueq as Compared to Neighbors for C16, C36
RESPONSE: Atom C16 is the pivot atom of a phenyl ring while C36 is pivot
to the thio benzyl group. It was commonly observed that the pivot atom
showed smaller thermal motion than the atoms of the pendent group with
wiggling action.
;
_vrf_PLAT340_PC-O2-145-C-shelxl
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.0095 Ang
RESPONSE: This may be to slight wiggling motion of the phenyl rings.
;
_vrf_PLAT063_PC-O2-145-C-shelxl
;
PROBLEM: Crystal Size Likely too Large for Beam Size .... 0.76 mm
RESPONSE: A larger size of crystal was used in order to compensate for the
lower diffracting power of the compound.
;
_vrf_PLAT072_PC-O2-145-C-shelxl
;
PROBLEM: SHELXL First Parameter in WGHT Unusually Large. 0.15
RESPONSE: This may be related to the large size of the crystal.
;
data_pc_03_020
_database_code_depnum_ccdc_archive 'CCDC 856812'
#TrackingRef '8501_web_deposit_cif_file_0_JunOU_1323064998.PC_03_020.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety '2(C43 H39 Br Cu Fe N P2), C2 H3 N'
_chemical_formula_sum 'C88 H81 Br2 Cu2 Fe2 N3 P4'
_chemical_formula_weight 1703.04
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 9.3018(3)
_cell_length_b 16.8469(5)
_cell_length_c 25.9616(8)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 4068.4(2)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 9907
_cell_measurement_theta_min 2.33
_cell_measurement_theta_max 21.28
_exptl_crystal_description Block
_exptl_crystal_colour gold
_exptl_crystal_size_max 0.52
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.36
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.390
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1740
_exptl_absorpt_coefficient_mu 1.971
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.4271
_exptl_absorpt_correction_T_max 0.5371
_exptl_absorpt_process_details 'SAINT ver. 7.34; Bruker SADABS'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_reflns_number 47426
_diffrn_reflns_av_R_equivalents 0.0634
_diffrn_reflns_av_sigmaI/netI 0.0545
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_l_min -32
_diffrn_reflns_limit_l_max 32
_diffrn_reflns_theta_min 2.62
_diffrn_reflns_theta_max 26.37
_reflns_number_total 8295
_reflns_number_gt 6180
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker APEX II'
_computing_cell_refinement 'Bruker APEX II'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
The crystal sample diffracted well from low to medium angle, but become very
weak at high angle. The overall data quality become compromised as a result.
A number of carbon atoms have relatively large thermal parameters, and required
restraining through ISOR. Due to considerations on the thermal parameters, the
lattice solvent acetonitrile was modelled to contain 50% occupancy. All protons
were refined on their theoretical positions.
;
_chemical_absolute_configuration syn
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0768P)^2^+1.7322P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.044(15)
_refine_ls_number_reflns 8295
_refine_ls_number_parameters 457
_refine_ls_number_restraints 57
_refine_ls_R_factor_all 0.0811
_refine_ls_R_factor_gt 0.0566
_refine_ls_wR_factor_ref 0.1487
_refine_ls_wR_factor_gt 0.1375
_refine_ls_goodness_of_fit_ref 1.072
_refine_ls_restrained_S_all 1.084
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.11104(9) -0.07915(4) 0.45170(4) 0.0591(2) Uani 1 1 d . . .
Cu1 Cu -0.15341(8) 0.01307(4) 0.33043(3) 0.05426(19) Uani 1 1 d . . .
Br1 Br -0.20274(11) -0.11340(5) 0.29878(4) 0.0989(3) Uani 1 1 d . . .
P1 P -0.16239(15) 0.04282(7) 0.41480(6) 0.0452(3) Uani 1 1 d . . .
P2 P -0.06465(17) 0.11365(10) 0.28180(6) 0.0575(4) Uani 1 1 d . . .
N1 N 0.3293(6) 0.0409(3) 0.3470(2) 0.0628(13) Uani 1 1 d . . .
C1 C 0.1072(10) -0.1737(4) 0.4014(5) 0.101(3) Uani 1 1 d . . .
H1A H 0.1192 -0.1710 0.3639 0.121 Uiso 1 1 calc R . .
C2 C 0.2176(11) -0.1814(5) 0.4379(5) 0.102(3) Uani 1 1 d U . .
H2A H 0.3204 -0.1858 0.4301 0.122 Uiso 1 1 calc R . .
C3 C 0.1587(13) -0.1847(4) 0.4856(5) 0.110(4) Uani 1 1 d . . .
H3A H 0.2128 -0.1909 0.5178 0.132 Uiso 1 1 calc R . .
C4 C 0.0011(13) -0.1737(4) 0.4821(5) 0.109(3) Uani 1 1 d . . .
H4A H -0.0697 -0.1737 0.5100 0.130 Uiso 1 1 calc R . .
C5 C -0.0235(9) -0.1687(4) 0.4285(5) 0.091(3) Uani 1 1 d . . .
H5A H -0.1179 -0.1607 0.4125 0.109 Uiso 1 1 calc R . .
C6 C 0.1972(7) 0.0029(3) 0.5010(3) 0.0632(15) Uani 1 1 d . . .
H6A H 0.2491 -0.0084 0.5330 0.076 Uiso 1 1 calc R . .
C7 C 0.0455(7) 0.0117(4) 0.4955(2) 0.0593(14) Uani 1 1 d . . .
H7A H -0.0251 0.0085 0.5234 0.071 Uiso 1 1 calc R . .
C8 C 0.0140(6) 0.0294(3) 0.4424(2) 0.0459(12) Uani 1 1 d . . .
C9 C 0.1499(6) 0.0285(2) 0.4156(2) 0.0461(12) Uani 1 1 d . . .
C10 C 0.2577(6) 0.0123(3) 0.4526(2) 0.0514(12) Uani 1 1 d . . .
H10A H 0.3603 0.0067 0.4448 0.062 Uiso 1 1 calc R . .
C11 C -0.2847(6) -0.0100(3) 0.4577(3) 0.0581(14) Uani 1 1 d . . .
C12 C -0.3449(6) -0.0812(4) 0.4411(3) 0.0734(19) Uani 1 1 d . . .
H12A H -0.3320 -0.0988 0.4075 0.088 Uiso 1 1 calc R . .
C13 C -0.4250(7) -0.1252(5) 0.4762(5) 0.090(3) Uani 1 1 d U . .
H13A H -0.4638 -0.1734 0.4655 0.108 Uiso 1 1 calc R . .
C14 C -0.4484(10) -0.1017(7) 0.5239(5) 0.113(4) Uani 1 1 d U . .
H14A H -0.5017 -0.1337 0.5459 0.136 Uiso 1 1 calc R . .
C15 C -0.3981(11) -0.0343(8) 0.5406(4) 0.119(4) Uani 1 1 d . . .
H15A H -0.4197 -0.0179 0.5739 0.143 Uiso 1 1 calc R . .
C16 C -0.3084(8) 0.0158(5) 0.5080(3) 0.088(2) Uani 1 1 d . . .
H16A H -0.2688 0.0629 0.5202 0.106 Uiso 1 1 calc R . .
C17 C -0.2093(6) 0.1459(3) 0.4307(2) 0.0492(13) Uani 1 1 d . . .
C18 C -0.3493(7) 0.1692(4) 0.4202(3) 0.0710(18) Uani 1 1 d . . .
H18A H -0.4152 0.1329 0.4071 0.085 Uiso 1 1 calc R . .
C19 C -0.3901(9) 0.2469(5) 0.4293(4) 0.098(3) Uani 1 1 d . . .
H19A H -0.4840 0.2627 0.4225 0.117 Uiso 1 1 calc R . .
C20 C -0.2947(10) 0.2999(4) 0.4481(4) 0.092(2) Uani 1 1 d . . .
H20A H -0.3218 0.3526 0.4528 0.110 Uiso 1 1 calc R . .
C21 C -0.1570(9) 0.2760(4) 0.4603(3) 0.081(2) Uani 1 1 d . . .
H21A H -0.0927 0.3121 0.4746 0.098 Uiso 1 1 calc R . .
C22 C -0.1136(7) 0.1977(3) 0.4514(3) 0.0626(15) Uani 1 1 d . . .
H22A H -0.0208 0.1815 0.4595 0.075 Uiso 1 1 calc R . .
C23 C 0.1775(6) 0.0554(3) 0.3611(2) 0.0496(13) Uani 1 1 d . . .
H23A H 0.1146 0.0261 0.3375 0.060 Uiso 1 1 calc R . .
C24 C 0.3547(8) -0.0434(5) 0.3374(3) 0.081(2) Uani 1 1 d . . .
H24A H 0.4486 -0.0503 0.3227 0.121 Uiso 1 1 calc R . .
H24B H 0.2835 -0.0631 0.3139 0.121 Uiso 1 1 calc R . .
H24C H 0.3487 -0.0721 0.3693 0.121 Uiso 1 1 calc R . .
C25 C 0.3791(8) 0.0865(5) 0.3023(3) 0.081(2) Uani 1 1 d . . .
H25A H 0.4724 0.0679 0.2920 0.122 Uiso 1 1 calc R . .
H25B H 0.3848 0.1417 0.3112 0.122 Uiso 1 1 calc R . .
H25C H 0.3127 0.0797 0.2743 0.122 Uiso 1 1 calc R . .
C26 C 0.1447(6) 0.1437(3) 0.3573(2) 0.0514(13) Uani 1 1 d . . .
C27 C 0.0490(6) 0.1773(4) 0.3215(2) 0.0553(14) Uani 1 1 d . . .
C28 C 0.0395(8) 0.2597(4) 0.3185(3) 0.0714(19) Uani 1 1 d . . .
H28A H -0.0215 0.2827 0.2943 0.086 Uiso 1 1 calc R . .
C29 C 0.1206(9) 0.3089(4) 0.3513(3) 0.086(2) Uani 1 1 d . . .
H29A H 0.1149 0.3638 0.3481 0.103 Uiso 1 1 calc R . .
C30 C 0.2060(9) 0.2763(4) 0.3870(3) 0.079(2) Uani 1 1 d . . .
H30A H 0.2548 0.3088 0.4101 0.095 Uiso 1 1 calc R . .
C31 C 0.2226(7) 0.1939(4) 0.3898(3) 0.0608(15) Uani 1 1 d . . .
H31A H 0.2861 0.1723 0.4137 0.073 Uiso 1 1 calc R . .
C32 C -0.2062(8) 0.1781(4) 0.2567(3) 0.078(2) Uani 1 1 d . . .
C33 C -0.2409(10) 0.1790(7) 0.2045(4) 0.116(4) Uani 1 1 d . . .
H33A H -0.1844 0.1520 0.1808 0.139 Uiso 1 1 calc R . .
C34 C -0.3619(13) 0.2210(8) 0.1886(5) 0.136(5) Uani 1 1 d . . .
H34A H -0.3869 0.2220 0.1539 0.163 Uiso 1 1 calc R . .
C35 C -0.4452(13) 0.2616(8) 0.2243(6) 0.130(4) Uani 1 1 d U . .
H35A H -0.5249 0.2903 0.2133 0.156 Uiso 1 1 calc R . .
C36 C -0.4117(12) 0.2597(7) 0.2746(6) 0.130(4) Uani 1 1 d U . .
H36A H -0.4684 0.2866 0.2984 0.156 Uiso 1 1 calc R . .
C37 C -0.2917(9) 0.2173(5) 0.2910(4) 0.099(3) Uani 1 1 d . . .
H37A H -0.2695 0.2156 0.3259 0.119 Uiso 1 1 calc R . .
C38 C 0.0477(8) 0.0932(4) 0.2260(3) 0.077(2) Uani 1 1 d D . .
C39 C 0.0625(8) 0.0144(5) 0.2099(3) 0.094(2) Uani 1 1 d D . .
H39 H 0.0113 -0.0259 0.2261 0.112 Uiso 1 1 calc R . .
C40 C 0.1562(11) -0.0028(9) 0.1687(4) 0.134(5) Uani 1 1 d D . .
H40A H 0.1692 -0.0547 0.1574 0.160 Uiso 1 1 calc R . .
C41 C 0.2282(14) 0.0596(8) 0.1457(4) 0.131(4) Uani 1 1 d DU . .
H41A H 0.2931 0.0483 0.1194 0.157 Uiso 1 1 calc R . .
C42 C 0.2084(12) 0.1376(8) 0.1597(4) 0.124(4) Uani 1 1 d DU . .
H42A H 0.2531 0.1782 0.1415 0.149 Uiso 1 1 calc R . .
C43 C 0.1196(9) 0.1549(6) 0.2021(3) 0.095(3) Uani 1 1 d D . .
H43 H 0.1094 0.2067 0.2138 0.114 Uiso 1 1 calc R . .
N1A N 0.5678(17) -0.0673(10) 0.1132(6) 0.100(4) Uiso 0.50 1 d P A 1
C1A C 0.5765(13) -0.0403(7) 0.1520(5) 0.054(3) Uiso 0.50 1 d P A 1
C2A C 0.578(2) -0.0187(11) 0.2008(7) 0.095(5) Uiso 0.50 1 d P A 1
H2AA H 0.5950 0.0374 0.2031 0.142 Uiso 0.50 1 calc PR A 1
H2AB H 0.6525 -0.0467 0.2186 0.142 Uiso 0.50 1 calc PR A 1
H2AC H 0.4865 -0.0309 0.2162 0.142 Uiso 0.50 1 calc PR A 1
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
Fe1 0.0605(5) 0.0324(4) 0.0843(6) 0.0070(4) -0.0106(5) 0.0019(3)
Cu1 0.0557(4) 0.0454(3) 0.0616(4) -0.0058(3) -0.0056(3) -0.0020(3)
Br1 0.1098(7) 0.0701(5) 0.1169(7) -0.0399(5) -0.0068(5) -0.0175(4)
P1 0.0477(7) 0.0322(6) 0.0557(8) -0.0004(5) 0.0042(7) -0.0017(5)
P2 0.0572(9) 0.0616(9) 0.0539(9) 0.0094(7) -0.0047(7) -0.0020(7)
N1 0.054(3) 0.064(3) 0.070(3) 0.000(2) 0.005(3) 0.011(2)
C1 0.082(5) 0.042(3) 0.179(9) -0.029(4) -0.016(6) 0.011(3)
C2 0.086(5) 0.056(4) 0.163(8) -0.010(5) -0.027(6) 0.015(4)
C3 0.128(8) 0.047(4) 0.156(10) 0.036(5) -0.054(8) -0.007(5)
C4 0.142(9) 0.032(3) 0.152(9) 0.029(4) 0.019(7) -0.001(4)
C5 0.073(5) 0.034(3) 0.167(9) -0.005(4) -0.017(5) -0.005(3)
C6 0.076(4) 0.040(3) 0.074(4) -0.001(3) -0.006(3) -0.004(3)
C7 0.069(4) 0.055(3) 0.054(3) 0.000(3) 0.003(3) -0.007(3)
C8 0.058(3) 0.027(2) 0.053(3) -0.001(2) 0.002(3) 0.003(2)
C9 0.049(3) 0.025(2) 0.065(3) -0.001(2) -0.001(3) 0.002(2)
C10 0.055(3) 0.038(2) 0.061(3) 0.003(2) -0.004(3) -0.005(2)
C11 0.048(3) 0.049(3) 0.077(4) 0.011(3) 0.011(3) -0.003(2)
C12 0.047(3) 0.051(3) 0.123(6) 0.025(4) -0.012(4) -0.007(3)
C13 0.049(4) 0.060(4) 0.160(8) 0.036(5) -0.004(5) -0.019(3)
C14 0.072(5) 0.114(7) 0.153(9) 0.073(7) 0.005(6) -0.027(5)
C15 0.110(7) 0.161(11) 0.085(6) 0.027(6) 0.040(6) 0.016(7)
C16 0.081(5) 0.088(5) 0.096(6) 0.026(4) 0.030(4) -0.014(4)
C17 0.059(3) 0.037(2) 0.052(3) -0.003(2) 0.014(3) -0.003(2)
C18 0.057(4) 0.054(3) 0.102(5) -0.010(3) -0.004(4) 0.010(3)
C19 0.068(4) 0.069(5) 0.156(8) -0.004(5) 0.009(5) 0.028(4)
C20 0.103(6) 0.056(4) 0.116(6) -0.016(4) 0.027(5) 0.014(4)
C21 0.083(5) 0.044(3) 0.117(6) -0.024(3) 0.008(5) -0.001(3)
C22 0.058(3) 0.051(3) 0.079(4) -0.008(3) 0.005(3) -0.004(3)
C23 0.047(3) 0.047(3) 0.055(3) -0.005(2) 0.001(2) 0.006(2)
C24 0.068(4) 0.087(5) 0.087(5) -0.015(4) 0.013(4) 0.017(4)
C25 0.060(4) 0.102(5) 0.081(5) 0.002(4) 0.023(4) -0.005(4)
C26 0.047(3) 0.045(3) 0.062(3) 0.004(2) 0.007(3) 0.000(2)
C27 0.056(3) 0.056(3) 0.054(3) 0.007(3) 0.001(3) -0.002(3)
C28 0.076(4) 0.051(3) 0.087(5) 0.027(3) -0.010(4) -0.001(3)
C29 0.090(5) 0.051(3) 0.116(6) 0.017(4) -0.011(5) -0.012(4)
C30 0.075(4) 0.055(4) 0.107(6) -0.003(4) -0.009(4) -0.015(3)
C31 0.060(3) 0.053(3) 0.070(4) 0.006(3) -0.001(3) -0.007(3)
C32 0.058(4) 0.075(4) 0.103(6) 0.042(4) -0.016(4) -0.015(3)
C33 0.080(6) 0.172(10) 0.096(6) 0.046(7) -0.024(5) -0.014(6)
C34 0.102(8) 0.161(11) 0.146(10) 0.071(9) -0.047(8) -0.020(8)
C35 0.089(6) 0.127(8) 0.173(10) 0.063(8) -0.022(7) -0.001(6)
C36 0.098(6) 0.106(7) 0.186(10) 0.033(7) 0.001(7) 0.011(6)
C37 0.067(5) 0.088(5) 0.142(8) 0.031(5) 0.021(5) 0.015(4)
C38 0.070(4) 0.107(6) 0.054(4) -0.007(4) -0.006(3) 0.002(4)
C39 0.072(4) 0.118(7) 0.092(6) -0.037(5) -0.006(4) -0.008(5)
C40 0.121(8) 0.202(13) 0.079(6) -0.053(8) -0.022(6) 0.015(9)
C41 0.113(7) 0.204(11) 0.076(6) -0.010(7) 0.022(5) -0.004(8)
C42 0.111(7) 0.180(10) 0.081(6) 0.012(6) 0.007(5) -0.018(7)
C43 0.097(6) 0.142(8) 0.046(4) 0.019(4) 0.006(4) -0.007(6)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C7 2.002(6) . ?
Fe1 C2 2.019(8) . ?
Fe1 C3 2.033(7) . ?
Fe1 C6 2.047(6) . ?
Fe1 C4 2.051(8) . ?
Fe1 C5 2.051(7) . ?
Fe1 C8 2.054(5) . ?
Fe1 C10 2.058(5) . ?
Fe1 C1 2.061(8) . ?
Fe1 C9 2.073(5) . ?
Cu1 P1 2.2484(16) . ?
Cu1 P2 2.2687(17) . ?
Cu1 Br1 2.3292(9) . ?
P1 C8 1.805(6) . ?
P1 C11 1.824(6) . ?
P1 C17 1.837(5) . ?
P2 C38 1.820(7) . ?
P2 C27 1.824(6) . ?
P2 C32 1.827(7) . ?
N1 C24 1.461(9) . ?
N1 C25 1.468(9) . ?
N1 C23 1.479(8) . ?
C1 C2 1.405(14) . ?
C1 C5 1.407(13) . ?
C1 H1A 0.9800 . ?
C2 C3 1.356(15) . ?
C2 H2A 0.9800 . ?
C3 C4 1.480(15) . ?
C3 H3A 0.9800 . ?
C4 C5 1.414(14) . ?
C4 H4A 0.9800 . ?
C5 H5A 0.9800 . ?
C6 C10 1.386(9) . ?
C6 C7 1.426(10) . ?
C6 H6A 0.9800 . ?
C7 C8 1.440(8) . ?
C7 H7A 0.9800 . ?
C8 C9 1.443(8) . ?
C9 C10 1.414(8) . ?
C9 C23 1.509(8) . ?
C10 H10A 0.9800 . ?
C11 C12 1.392(9) . ?
C11 C16 1.394(11) . ?
C12 C13 1.391(11) . ?
C12 H12A 0.9300 . ?
C13 C14 1.317(15) . ?
C13 H13A 0.9300 . ?
C14 C15 1.303(16) . ?
C14 H14A 0.9300 . ?
C15 C16 1.457(13) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C22 1.359(8) . ?
C17 C18 1.387(9) . ?
C18 C19 1.383(10) . ?
C18 H18A 0.9300 . ?
C19 C20 1.351(12) . ?
C19 H19A 0.9300 . ?
C20 C21 1.380(12) . ?
C20 H20A 0.9300 . ?
C21 C22 1.398(9) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
C23 C26 1.521(8) . ?
C23 H23A 0.9800 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C31 1.398(8) . ?
C26 C27 1.406(8) . ?
C27 C28 1.394(9) . ?
C28 C29 1.407(10) . ?
C28 H28A 0.9300 . ?
C29 C30 1.338(11) . ?
C29 H29A 0.9300 . ?
C30 C31 1.399(9) . ?
C30 H30A 0.9300 . ?
C31 H31A 0.9300 . ?
C32 C37 1.364(12) . ?
C32 C33 1.392(12) . ?
C33 C34 1.392(15) . ?
C33 H33A 0.9300 . ?
C34 C35 1.389(18) . ?
C34 H34A 0.9300 . ?
C35 C36 1.342(17) . ?
C35 H35A 0.9300 . ?
C36 C37 1.392(14) . ?
C36 H36A 0.9300 . ?
C37 H37A 0.9300 . ?
C38 C43 1.383(9) . ?
C38 C39 1.397(9) . ?
C39 C40 1.410(10) . ?
C39 H39 0.9300 . ?
C40 C41 1.383(11) . ?
C40 H40A 0.9300 . ?
C41 C42 1.376(11) . ?
C41 H41A 0.9300 . ?
C42 C43 1.405(10) . ?
C42 H42A 0.9300 . ?
C43 H43 0.9300 . ?
N1A C1A 1.108(17) . ?
C1A C2A 1.32(2) . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 Fe1 C2 154.5(4) . . ?
C7 Fe1 C3 119.3(4) . . ?
C2 Fe1 C3 39.1(4) . . ?
C7 Fe1 C6 41.2(3) . . ?
C2 Fe1 C6 119.6(3) . . ?
C3 Fe1 C6 103.5(4) . . ?
C7 Fe1 C4 102.9(4) . . ?
C2 Fe1 C4 69.5(5) . . ?
C3 Fe1 C4 42.5(4) . . ?
C6 Fe1 C4 118.6(4) . . ?
C7 Fe1 C5 122.9(3) . . ?
C2 Fe1 C5 67.7(3) . . ?
C3 Fe1 C5 67.5(4) . . ?
C6 Fe1 C5 156.9(4) . . ?
C4 Fe1 C5 40.3(4) . . ?
C7 Fe1 C8 41.6(2) . . ?
C2 Fe1 C8 162.7(4) . . ?
C3 Fe1 C8 157.7(4) . . ?
C6 Fe1 C8 69.1(2) . . ?
C4 Fe1 C8 121.2(3) . . ?
C5 Fe1 C8 110.6(3) . . ?
C7 Fe1 C10 67.9(2) . . ?
C2 Fe1 C10 108.4(3) . . ?
C3 Fe1 C10 120.4(3) . . ?
C6 Fe1 C10 39.5(2) . . ?
C4 Fe1 C10 155.2(4) . . ?
C5 Fe1 C10 163.4(4) . . ?
C8 Fe1 C10 68.0(2) . . ?
C7 Fe1 C1 161.1(3) . . ?
C2 Fe1 C1 40.3(4) . . ?
C3 Fe1 C1 66.6(4) . . ?
C6 Fe1 C1 157.7(3) . . ?
C4 Fe1 C1 68.6(4) . . ?
C5 Fe1 C1 40.0(4) . . ?
C8 Fe1 C1 127.3(3) . . ?
C10 Fe1 C1 126.7(3) . . ?
C7 Fe1 C9 68.9(2) . . ?
C2 Fe1 C9 125.5(4) . . ?
C3 Fe1 C9 157.3(4) . . ?
C6 Fe1 C9 67.9(2) . . ?
C4 Fe1 C9 160.1(4) . . ?
C5 Fe1 C9 128.1(3) . . ?
C8 Fe1 C9 40.9(2) . . ?
C10 Fe1 C9 40.0(2) . . ?
C1 Fe1 C9 113.1(3) . . ?
P1 Cu1 P2 112.90(6) . . ?
P1 Cu1 Br1 122.70(5) . . ?
P2 Cu1 Br1 123.96(6) . . ?
C8 P1 C11 105.3(3) . . ?
C8 P1 C17 104.2(2) . . ?
C11 P1 C17 100.1(3) . . ?
C8 P1 Cu1 109.00(18) . . ?
C11 P1 Cu1 120.6(2) . . ?
C17 P1 Cu1 115.99(19) . . ?
C38 P2 C27 103.2(3) . . ?
C38 P2 C32 104.0(4) . . ?
C27 P2 C32 105.7(3) . . ?
C38 P2 Cu1 120.7(3) . . ?
C27 P2 Cu1 109.60(19) . . ?
C32 P2 Cu1 112.3(2) . . ?
C24 N1 C25 108.8(6) . . ?
C24 N1 C23 110.9(5) . . ?
C25 N1 C23 114.2(5) . . ?
C2 C1 C5 107.4(10) . . ?
C2 C1 Fe1 68.3(5) . . ?
C5 C1 Fe1 69.6(5) . . ?
C2 C1 H1A 126.3 . . ?
C5 C1 H1A 126.3 . . ?
Fe1 C1 H1A 126.3 . . ?
C3 C2 C1 109.0(9) . . ?
C3 C2 Fe1 71.0(5) . . ?
C1 C2 Fe1 71.5(4) . . ?
C3 C2 H2A 125.5 . . ?
C1 C2 H2A 125.5 . . ?
Fe1 C2 H2A 125.5 . . ?
C2 C3 C4 109.8(10) . . ?
C2 C3 Fe1 69.9(5) . . ?
C4 C3 Fe1 69.4(4) . . ?
C2 C3 H3A 125.1 . . ?
C4 C3 H3A 125.1 . . ?
Fe1 C3 H3A 125.1 . . ?
C5 C4 C3 103.2(10) . . ?
C5 C4 Fe1 69.8(5) . . ?
C3 C4 Fe1 68.1(5) . . ?
C5 C4 H4A 128.3 . . ?
C3 C4 H4A 128.3 . . ?
Fe1 C4 H4A 128.3 . . ?
C1 C5 C4 110.4(9) . . ?
C1 C5 Fe1 70.3(4) . . ?
C4 C5 Fe1 69.8(5) . . ?
C1 C5 H5A 124.8 . . ?
C4 C5 H5A 124.8 . . ?
Fe1 C5 H5A 124.8 . . ?
C10 C6 C7 107.4(6) . . ?
C10 C6 Fe1 70.7(3) . . ?
C7 C6 Fe1 67.7(4) . . ?
C10 C6 H6A 126.3 . . ?
C7 C6 H6A 126.3 . . ?
Fe1 C6 H6A 126.3 . . ?
C6 C7 C8 108.6(6) . . ?
C6 C7 Fe1 71.1(4) . . ?
C8 C7 Fe1 71.2(3) . . ?
C6 C7 H7A 125.7 . . ?
C8 C7 H7A 125.7 . . ?
Fe1 C7 H7A 125.7 . . ?
C7 C8 C9 106.3(5) . . ?
C7 C8 P1 126.3(4) . . ?
C9 C8 P1 127.3(4) . . ?
C7 C8 Fe1 67.3(3) . . ?
C9 C8 Fe1 70.3(3) . . ?
P1 C8 Fe1 123.9(3) . . ?
C10 C9 C8 107.2(5) . . ?
C10 C9 C23 125.0(5) . . ?
C8 C9 C23 126.7(5) . . ?
C10 C9 Fe1 69.4(3) . . ?
C8 C9 Fe1 68.8(3) . . ?
C23 C9 Fe1 135.7(3) . . ?
C6 C10 C9 110.5(5) . . ?
C6 C10 Fe1 69.8(3) . . ?
C9 C10 Fe1 70.6(3) . . ?
C6 C10 H10A 124.8 . . ?
C9 C10 H10A 124.8 . . ?
Fe1 C10 H10A 124.8 . . ?
C12 C11 C16 119.7(6) . . ?
C12 C11 P1 118.8(5) . . ?
C16 C11 P1 121.2(5) . . ?
C13 C12 C11 118.2(8) . . ?
C13 C12 H12A 120.9 . . ?
C11 C12 H12A 120.9 . . ?
C14 C13 C12 122.9(8) . . ?
C14 C13 H13A 118.5 . . ?
C12 C13 H13A 118.5 . . ?
C15 C14 C13 121.1(8) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C14 C15 C16 121.2(10) . . ?
C14 C15 H15A 119.4 . . ?
C16 C15 H15A 119.4 . . ?
C11 C16 C15 116.9(9) . . ?
C11 C16 H16A 121.5 . . ?
C15 C16 H16A 121.5 . . ?
C22 C17 C18 120.7(5) . . ?
C22 C17 P1 122.8(5) . . ?
C18 C17 P1 116.5(4) . . ?
C19 C18 C17 119.5(7) . . ?
C19 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
C20 C19 C18 120.5(7) . . ?
C20 C19 H19A 119.7 . . ?
C18 C19 H19A 119.7 . . ?
C19 C20 C21 120.0(7) . . ?
C19 C20 H20A 120.0 . . ?
C21 C20 H20A 120.0 . . ?
C20 C21 C22 120.4(7) . . ?
C20 C21 H21A 119.8 . . ?
C22 C21 H21A 119.8 . . ?
C17 C22 C21 118.9(6) . . ?
C17 C22 H22A 120.6 . . ?
C21 C22 H22A 120.6 . . ?
N1 C23 C9 110.1(5) . . ?
N1 C23 C26 109.7(5) . . ?
C9 C23 C26 108.6(4) . . ?
N1 C23 H23A 109.5 . . ?
C9 C23 H23A 109.5 . . ?
C26 C23 H23A 109.5 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C31 C26 C27 118.9(5) . . ?
C31 C26 C23 116.7(5) . . ?
C27 C26 C23 124.3(5) . . ?
C28 C27 C26 118.6(6) . . ?
C28 C27 P2 121.1(5) . . ?
C26 C27 P2 120.2(5) . . ?
C27 C28 C29 121.2(6) . . ?
C27 C28 H28A 119.4 . . ?
C29 C28 H28A 119.4 . . ?
C30 C29 C28 119.7(7) . . ?
C30 C29 H29A 120.1 . . ?
C28 C29 H29A 120.1 . . ?
C29 C30 C31 120.6(7) . . ?
C29 C30 H30A 119.7 . . ?
C31 C30 H30A 119.7 . . ?
C26 C31 C30 120.7(6) . . ?
C26 C31 H31A 119.6 . . ?
C30 C31 H31A 119.6 . . ?
C37 C32 C33 119.6(8) . . ?
C37 C32 P2 118.4(6) . . ?
C33 C32 P2 121.4(8) . . ?
C32 C33 C34 118.8(12) . . ?
C32 C33 H33A 120.6 . . ?
C34 C33 H33A 120.6 . . ?
C35 C34 C33 120.2(11) . . ?
C35 C34 H34A 119.9 . . ?
C33 C34 H34A 119.9 . . ?
C36 C35 C34 120.5(11) . . ?
C36 C35 H35A 119.7 . . ?
C34 C35 H35A 119.7 . . ?
C35 C36 C37 119.7(13) . . ?
C35 C36 H36A 120.1 . . ?
C37 C36 H36A 120.1 . . ?
C32 C37 C36 121.1(11) . . ?
C32 C37 H37A 119.5 . . ?
C36 C37 H37A 119.5 . . ?
C43 C38 C39 122.1(7) . . ?
C43 C38 P2 119.5(6) . . ?
C39 C38 P2 118.3(6) . . ?
C38 C39 C40 118.9(9) . . ?
C38 C39 H39 120.6 . . ?
C40 C39 H39 120.6 . . ?
C41 C40 C39 118.1(11) . . ?
C41 C40 H40A 120.9 . . ?
C39 C40 H40A 120.9 . . ?
C42 C41 C40 123.1(11) . . ?
C42 C41 H41A 118.4 . . ?
C40 C41 H41A 118.4 . . ?
C41 C42 C43 118.9(10) . . ?
C41 C42 H42A 120.6 . . ?
C43 C42 H42A 120.6 . . ?
C38 C43 C42 118.7(9) . . ?
C38 C43 H43 120.7 . . ?
C42 C43 H43 120.7 . . ?
N1A C1A C2A 171.0(16) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P2 Cu1 P1 C8 -80.56(18) . . . . ?
Br1 Cu1 P1 C8 92.10(18) . . . . ?
P2 Cu1 P1 C11 157.6(2) . . . . ?
Br1 Cu1 P1 C11 -29.7(2) . . . . ?
P2 Cu1 P1 C17 36.6(2) . . . . ?
Br1 Cu1 P1 C17 -150.8(2) . . . . ?
P1 Cu1 P2 C38 144.0(3) . . . . ?
Br1 Cu1 P2 C38 -28.6(3) . . . . ?
P1 Cu1 P2 C27 24.4(2) . . . . ?
Br1 Cu1 P2 C27 -148.1(2) . . . . ?
P1 Cu1 P2 C32 -92.7(3) . . . . ?
Br1 Cu1 P2 C32 94.7(3) . . . . ?
C7 Fe1 C1 C2 -149.4(10) . . . . ?
C3 Fe1 C1 C2 -37.1(6) . . . . ?
C6 Fe1 C1 C2 30.4(13) . . . . ?
C4 Fe1 C1 C2 -83.2(7) . . . . ?
C5 Fe1 C1 C2 -119.5(9) . . . . ?
C8 Fe1 C1 C2 163.2(6) . . . . ?
C10 Fe1 C1 C2 74.3(8) . . . . ?
C9 Fe1 C1 C2 118.2(7) . . . . ?
C7 Fe1 C1 C5 -29.9(14) . . . . ?
C2 Fe1 C1 C5 119.5(9) . . . . ?
C3 Fe1 C1 C5 82.4(7) . . . . ?
C6 Fe1 C1 C5 149.8(8) . . . . ?
C4 Fe1 C1 C5 36.2(6) . . . . ?
C8 Fe1 C1 C5 -77.4(7) . . . . ?
C10 Fe1 C1 C5 -166.3(5) . . . . ?
C9 Fe1 C1 C5 -122.3(6) . . . . ?
C5 C1 C2 C3 2.6(9) . . . . ?
Fe1 C1 C2 C3 61.4(6) . . . . ?
C5 C1 C2 Fe1 -58.8(5) . . . . ?
C7 Fe1 C2 C3 38.9(11) . . . . ?
C6 Fe1 C2 C3 74.2(7) . . . . ?
C4 Fe1 C2 C3 -37.9(7) . . . . ?
C5 Fe1 C2 C3 -81.3(7) . . . . ?
C8 Fe1 C2 C3 -169.2(9) . . . . ?
C10 Fe1 C2 C3 115.8(6) . . . . ?
C1 Fe1 C2 C3 -118.6(9) . . . . ?
C9 Fe1 C2 C3 156.9(5) . . . . ?
C7 Fe1 C2 C1 157.5(7) . . . . ?
C3 Fe1 C2 C1 118.6(9) . . . . ?
C6 Fe1 C2 C1 -167.2(6) . . . . ?
C4 Fe1 C2 C1 80.7(7) . . . . ?
C5 Fe1 C2 C1 37.3(6) . . . . ?
C8 Fe1 C2 C1 -50.6(13) . . . . ?
C10 Fe1 C2 C1 -125.6(6) . . . . ?
C9 Fe1 C2 C1 -84.5(7) . . . . ?
C1 C2 C3 C4 -3.7(10) . . . . ?
Fe1 C2 C3 C4 58.0(6) . . . . ?
C1 C2 C3 Fe1 -61.7(5) . . . . ?
C7 Fe1 C3 C2 -161.9(5) . . . . ?
C6 Fe1 C3 C2 -120.7(6) . . . . ?
C4 Fe1 C3 C2 121.5(10) . . . . ?
C5 Fe1 C3 C2 81.8(6) . . . . ?
C8 Fe1 C3 C2 171.6(7) . . . . ?
C10 Fe1 C3 C2 -81.8(6) . . . . ?
C1 Fe1 C3 C2 38.2(6) . . . . ?
C9 Fe1 C3 C2 -56.1(12) . . . . ?
C7 Fe1 C3 C4 76.5(7) . . . . ?
C2 Fe1 C3 C4 -121.5(10) . . . . ?
C6 Fe1 C3 C4 117.8(7) . . . . ?
C5 Fe1 C3 C4 -39.7(6) . . . . ?
C8 Fe1 C3 C4 50.0(12) . . . . ?
C10 Fe1 C3 C4 156.6(6) . . . . ?
C1 Fe1 C3 C4 -83.3(7) . . . . ?
C9 Fe1 C3 C4 -177.6(7) . . . . ?
C2 C3 C4 C5 3.3(9) . . . . ?
Fe1 C3 C4 C5 61.6(5) . . . . ?
C2 C3 C4 Fe1 -58.3(6) . . . . ?
C7 Fe1 C4 C5 126.3(5) . . . . ?
C2 Fe1 C4 C5 -79.2(6) . . . . ?
C3 Fe1 C4 C5 -114.2(9) . . . . ?
C6 Fe1 C4 C5 167.4(5) . . . . ?
C8 Fe1 C4 C5 85.6(6) . . . . ?
C10 Fe1 C4 C5 -168.9(6) . . . . ?
C1 Fe1 C4 C5 -36.0(5) . . . . ?
C9 Fe1 C4 C5 63.1(13) . . . . ?
C7 Fe1 C4 C3 -119.5(7) . . . . ?
C2 Fe1 C4 C3 35.0(6) . . . . ?
C6 Fe1 C4 C3 -78.4(8) . . . . ?
C5 Fe1 C4 C3 114.2(9) . . . . ?
C8 Fe1 C4 C3 -160.1(6) . . . . ?
C10 Fe1 C4 C3 -54.7(11) . . . . ?
C1 Fe1 C4 C3 78.2(7) . . . . ?
C9 Fe1 C4 C3 177.3(9) . . . . ?
C2 C1 C5 C4 -0.4(8) . . . . ?
Fe1 C1 C5 C4 -58.4(5) . . . . ?
C2 C1 C5 Fe1 58.0(5) . . . . ?
C3 C4 C5 C1 -1.7(8) . . . . ?
Fe1 C4 C5 C1 58.7(5) . . . . ?
C3 C4 C5 Fe1 -60.4(5) . . . . ?
C7 Fe1 C5 C1 168.9(5) . . . . ?
C2 Fe1 C5 C1 -37.5(6) . . . . ?
C3 Fe1 C5 C1 -79.9(7) . . . . ?
C6 Fe1 C5 C1 -151.0(7) . . . . ?
C4 Fe1 C5 C1 -121.7(8) . . . . ?
C8 Fe1 C5 C1 124.0(5) . . . . ?
C10 Fe1 C5 C1 41.9(12) . . . . ?
C9 Fe1 C5 C1 80.9(6) . . . . ?
C7 Fe1 C5 C4 -69.4(6) . . . . ?
C2 Fe1 C5 C4 84.3(7) . . . . ?
C3 Fe1 C5 C4 41.8(7) . . . . ?
C6 Fe1 C5 C4 -29.2(10) . . . . ?
C8 Fe1 C5 C4 -114.3(6) . . . . ?
C10 Fe1 C5 C4 163.6(9) . . . . ?
C1 Fe1 C5 C4 121.7(8) . . . . ?
C9 Fe1 C5 C4 -157.3(5) . . . . ?
C7 Fe1 C6 C10 -119.1(5) . . . . ?
C2 Fe1 C6 C10 83.1(6) . . . . ?
C3 Fe1 C6 C10 121.7(5) . . . . ?
C4 Fe1 C6 C10 164.6(4) . . . . ?
C5 Fe1 C6 C10 -174.3(7) . . . . ?
C8 Fe1 C6 C10 -80.4(4) . . . . ?
C1 Fe1 C6 C10 61.0(10) . . . . ?
C9 Fe1 C6 C10 -36.2(3) . . . . ?
C2 Fe1 C6 C7 -157.8(5) . . . . ?
C3 Fe1 C6 C7 -119.2(5) . . . . ?
C4 Fe1 C6 C7 -76.3(5) . . . . ?
C5 Fe1 C6 C7 -55.2(9) . . . . ?
C8 Fe1 C6 C7 38.7(4) . . . . ?
C10 Fe1 C6 C7 119.1(5) . . . . ?
C1 Fe1 C6 C7 -179.9(9) . . . . ?
C9 Fe1 C6 C7 82.9(4) . . . . ?
C10 C6 C7 C8 -1.8(7) . . . . ?
Fe1 C6 C7 C8 -61.6(4) . . . . ?
C10 C6 C7 Fe1 59.8(4) . . . . ?
C2 Fe1 C7 C6 49.6(10) . . . . ?
C3 Fe1 C7 C6 76.6(5) . . . . ?
C4 Fe1 C7 C6 119.0(5) . . . . ?
C5 Fe1 C7 C6 157.4(5) . . . . ?
C8 Fe1 C7 C6 -118.2(5) . . . . ?
C10 Fe1 C7 C6 -36.8(4) . . . . ?
C1 Fe1 C7 C6 179.9(11) . . . . ?
C9 Fe1 C7 C6 -80.0(4) . . . . ?
C2 Fe1 C7 C8 167.8(8) . . . . ?
C3 Fe1 C7 C8 -165.2(4) . . . . ?
C6 Fe1 C7 C8 118.2(5) . . . . ?
C4 Fe1 C7 C8 -122.8(5) . . . . ?
C5 Fe1 C7 C8 -84.4(5) . . . . ?
C10 Fe1 C7 C8 81.4(4) . . . . ?
C1 Fe1 C7 C8 -61.9(12) . . . . ?
C9 Fe1 C7 C8 38.2(3) . . . . ?
C6 C7 C8 C9 1.9(6) . . . . ?
Fe1 C7 C8 C9 -59.7(3) . . . . ?
C6 C7 C8 P1 177.8(4) . . . . ?
Fe1 C7 C8 P1 116.2(4) . . . . ?
C6 C7 C8 Fe1 61.6(4) . . . . ?
C11 P1 C8 C7 -23.3(5) . . . . ?
C17 P1 C8 C7 81.5(5) . . . . ?
Cu1 P1 C8 C7 -154.1(4) . . . . ?
C11 P1 C8 C9 151.8(4) . . . . ?
C17 P1 C8 C9 -103.3(4) . . . . ?
Cu1 P1 C8 C9 21.1(5) . . . . ?
C11 P1 C8 Fe1 61.8(4) . . . . ?
C17 P1 C8 Fe1 166.7(3) . . . . ?
Cu1 P1 C8 Fe1 -68.9(3) . . . . ?
C2 Fe1 C8 C7 -162.2(10) . . . . ?
C3 Fe1 C8 C7 36.0(9) . . . . ?
C6 Fe1 C8 C7 -38.4(4) . . . . ?
C4 Fe1 C8 C7 73.2(5) . . . . ?
C5 Fe1 C8 C7 116.8(5) . . . . ?
C10 Fe1 C8 C7 -80.9(4) . . . . ?
C1 Fe1 C8 C7 158.9(5) . . . . ?
C9 Fe1 C8 C7 -118.3(5) . . . . ?
C7 Fe1 C8 C9 118.3(5) . . . . ?
C2 Fe1 C8 C9 -43.9(11) . . . . ?
C3 Fe1 C8 C9 154.2(8) . . . . ?
C6 Fe1 C8 C9 79.8(3) . . . . ?
C4 Fe1 C8 C9 -168.5(5) . . . . ?
C5 Fe1 C8 C9 -124.9(4) . . . . ?
C10 Fe1 C8 C9 37.3(3) . . . . ?
C1 Fe1 C8 C9 -82.8(5) . . . . ?
C7 Fe1 C8 P1 -119.4(5) . . . . ?
C2 Fe1 C8 P1 78.4(11) . . . . ?
C3 Fe1 C8 P1 -83.4(9) . . . . ?
C6 Fe1 C8 P1 -157.8(4) . . . . ?
C4 Fe1 C8 P1 -46.2(6) . . . . ?
C5 Fe1 C8 P1 -2.6(5) . . . . ?
C10 Fe1 C8 P1 159.7(4) . . . . ?
C1 Fe1 C8 P1 39.5(6) . . . . ?
C9 Fe1 C8 P1 122.3(5) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
P1 C8 C9 C10 -177.1(4) . . . . ?
Fe1 C8 C9 C10 -59.0(3) . . . . ?
C7 C8 C9 C23 -170.2(5) . . . . ?
P1 C8 C9 C23 13.9(7) . . . . ?
Fe1 C8 C9 C23 132.0(5) . . . . ?
C7 C8 C9 Fe1 57.8(4) . . . . ?
P1 C8 C9 Fe1 -118.1(4) . . . . ?
C7 Fe1 C9 C10 80.2(4) . . . . ?
C2 Fe1 C9 C10 -75.7(5) . . . . ?
C3 Fe1 C9 C10 -35.7(11) . . . . ?
C6 Fe1 C9 C10 35.7(3) . . . . ?
C4 Fe1 C9 C10 149.0(11) . . . . ?
C5 Fe1 C9 C10 -163.8(4) . . . . ?
C8 Fe1 C9 C10 119.0(4) . . . . ?
C1 Fe1 C9 C10 -120.1(4) . . . . ?
C7 Fe1 C9 C8 -38.8(3) . . . . ?
C2 Fe1 C9 C8 165.3(4) . . . . ?
C3 Fe1 C9 C8 -154.7(10) . . . . ?
C6 Fe1 C9 C8 -83.2(4) . . . . ?
C4 Fe1 C9 C8 30.0(12) . . . . ?
C5 Fe1 C9 C8 77.2(5) . . . . ?
C10 Fe1 C9 C8 -119.0(4) . . . . ?
C1 Fe1 C9 C8 120.9(4) . . . . ?
C7 Fe1 C9 C23 -160.2(6) . . . . ?
C2 Fe1 C9 C23 43.9(7) . . . . ?
C3 Fe1 C9 C23 83.9(12) . . . . ?
C6 Fe1 C9 C23 155.3(6) . . . . ?
C4 Fe1 C9 C23 -91.4(12) . . . . ?
C5 Fe1 C9 C23 -44.2(7) . . . . ?
C8 Fe1 C9 C23 -121.4(7) . . . . ?
C10 Fe1 C9 C23 119.6(7) . . . . ?
C1 Fe1 C9 C23 -0.5(6) . . . . ?
C7 C6 C10 C9 1.1(6) . . . . ?
Fe1 C6 C10 C9 59.0(4) . . . . ?
C7 C6 C10 Fe1 -57.9(4) . . . . ?
C8 C9 C10 C6 0.1(6) . . . . ?
C23 C9 C10 C6 169.3(5) . . . . ?
Fe1 C9 C10 C6 -58.5(4) . . . . ?
C8 C9 C10 Fe1 58.6(3) . . . . ?
C23 C9 C10 Fe1 -132.1(5) . . . . ?
C7 Fe1 C10 C6 38.4(4) . . . . ?
C2 Fe1 C10 C6 -114.6(5) . . . . ?
C3 Fe1 C10 C6 -73.5(6) . . . . ?
C4 Fe1 C10 C6 -33.7(9) . . . . ?
C5 Fe1 C10 C6 172.1(9) . . . . ?
C8 Fe1 C10 C6 83.5(4) . . . . ?
C1 Fe1 C10 C6 -155.5(5) . . . . ?
C9 Fe1 C10 C6 121.6(5) . . . . ?
C7 Fe1 C10 C9 -83.2(3) . . . . ?
C2 Fe1 C10 C9 123.8(5) . . . . ?
C3 Fe1 C10 C9 164.9(5) . . . . ?
C6 Fe1 C10 C9 -121.6(5) . . . . ?
C4 Fe1 C10 C9 -155.4(8) . . . . ?
C5 Fe1 C10 C9 50.5(10) . . . . ?
C8 Fe1 C10 C9 -38.2(3) . . . . ?
C1 Fe1 C10 C9 82.8(5) . . . . ?
C8 P1 C11 C12 -107.5(5) . . . . ?
C17 P1 C11 C12 144.6(5) . . . . ?
Cu1 P1 C11 C12 16.1(6) . . . . ?
C8 P1 C11 C16 66.7(6) . . . . ?
C17 P1 C11 C16 -41.1(6) . . . . ?
Cu1 P1 C11 C16 -169.7(5) . . . . ?
C16 C11 C12 C13 -1.4(9) . . . . ?
P1 C11 C12 C13 173.0(5) . . . . ?
C11 C12 C13 C14 1.4(11) . . . . ?
C12 C13 C14 C15 0.8(15) . . . . ?
C13 C14 C15 C16 -2.9(16) . . . . ?
C12 C11 C16 C15 -0.6(11) . . . . ?
P1 C11 C16 C15 -174.8(6) . . . . ?
C14 C15 C16 C11 2.8(14) . . . . ?
C8 P1 C17 C22 9.0(6) . . . . ?
C11 P1 C17 C22 117.7(5) . . . . ?
Cu1 P1 C17 C22 -110.7(5) . . . . ?
C8 P1 C17 C18 -171.3(5) . . . . ?
C11 P1 C17 C18 -62.6(5) . . . . ?
Cu1 P1 C17 C18 68.9(5) . . . . ?
C22 C17 C18 C19 2.2(11) . . . . ?
P1 C17 C18 C19 -177.5(6) . . . . ?
C17 C18 C19 C20 0.3(13) . . . . ?
C18 C19 C20 C21 -2.7(14) . . . . ?
C19 C20 C21 C22 2.6(14) . . . . ?
C18 C17 C22 C21 -2.2(10) . . . . ?
P1 C17 C22 C21 177.4(6) . . . . ?
C20 C21 C22 C17 -0.2(12) . . . . ?
C24 N1 C23 C9 75.0(6) . . . . ?
C25 N1 C23 C9 -161.6(5) . . . . ?
C24 N1 C23 C26 -165.4(5) . . . . ?
C25 N1 C23 C26 -42.1(7) . . . . ?
C10 C9 C23 N1 15.9(7) . . . . ?
C8 C9 C23 N1 -177.0(5) . . . . ?
Fe1 C9 C23 N1 -80.1(6) . . . . ?
C10 C9 C23 C26 -104.3(5) . . . . ?
C8 C9 C23 C26 62.9(6) . . . . ?
Fe1 C9 C23 C26 159.7(4) . . . . ?
N1 C23 C26 C31 -61.8(7) . . . . ?
C9 C23 C26 C31 58.6(7) . . . . ?
N1 C23 C26 C27 114.1(6) . . . . ?
C9 C23 C26 C27 -125.4(6) . . . . ?
C31 C26 C27 C28 2.4(9) . . . . ?
C23 C26 C27 C28 -173.4(6) . . . . ?
C31 C26 C27 P2 -175.3(5) . . . . ?
C23 C26 C27 P2 8.8(8) . . . . ?
C38 P2 C27 C28 94.3(6) . . . . ?
C32 P2 C27 C28 -14.7(6) . . . . ?
Cu1 P2 C27 C28 -135.9(5) . . . . ?
C38 P2 C27 C26 -88.1(5) . . . . ?
C32 P2 C27 C26 163.0(5) . . . . ?
Cu1 P2 C27 C26 41.7(5) . . . . ?
C26 C27 C28 C29 -1.7(10) . . . . ?
P2 C27 C28 C29 176.0(6) . . . . ?
C27 C28 C29 C30 -1.6(12) . . . . ?
C28 C29 C30 C31 4.1(13) . . . . ?
C27 C26 C31 C30 0.0(9) . . . . ?
C23 C26 C31 C30 176.2(6) . . . . ?
C29 C30 C31 C26 -3.4(12) . . . . ?
C38 P2 C32 C37 -166.8(6) . . . . ?
C27 P2 C32 C37 -58.4(7) . . . . ?
Cu1 P2 C32 C37 61.0(7) . . . . ?
C38 P2 C32 C33 22.4(7) . . . . ?
C27 P2 C32 C33 130.8(7) . . . . ?
Cu1 P2 C32 C33 -109.8(7) . . . . ?
C37 C32 C33 C34 0.8(14) . . . . ?
P2 C32 C33 C34 171.5(8) . . . . ?
C32 C33 C34 C35 0.4(16) . . . . ?
C33 C34 C35 C36 -1.1(19) . . . . ?
C34 C35 C36 C37 0.5(18) . . . . ?
C33 C32 C37 C36 -1.4(13) . . . . ?
P2 C32 C37 C36 -172.4(7) . . . . ?
C35 C36 C37 C32 0.7(16) . . . . ?
C27 P2 C38 C43 -46.7(7) . . . . ?
C32 P2 C38 C43 63.4(7) . . . . ?
Cu1 P2 C38 C43 -169.4(5) . . . . ?
C27 P2 C38 C39 130.9(6) . . . . ?
C32 P2 C38 C39 -118.9(6) . . . . ?
Cu1 P2 C38 C39 8.2(7) . . . . ?
C43 C38 C39 C40 1.5(12) . . . . ?
P2 C38 C39 C40 -176.1(6) . . . . ?
C38 C39 C40 C41 -0.7(14) . . . . ?
C39 C40 C41 C42 -2.6(17) . . . . ?
C40 C41 C42 C43 5.1(18) . . . . ?
C39 C38 C43 C42 1.0(12) . . . . ?
P2 C38 C43 C42 178.6(7) . . . . ?
C41 C42 C43 C38 -4.2(15) . . . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 26.37
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.555
_refine_diff_density_min -0.320
_refine_diff_density_rms 0.079