# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2011
#data_New_Global_Publ_Block
data_global
_journal_name_full 'Dalton Trans.'
#TrackingRef '- czepaper_revised.cif'
_journal_coden_Cambridge 0222
_audit_update_record
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2010-05-25 # Formatted by publCIF
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_audit_creation_method
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manual editing of the CIF file
created by SHELXTL Ver. 6.10
and processed with modiCIfer-03272007.
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# 1. SUBMISSION DETAILS
_publ_contact_author_name 'Guzei, Ilia A.'
_publ_contact_author_address
;
Department of Chemistry
University of Wisconsin-Madison
1101 University Ave
Madison, WI 53706
USA
;
_publ_contact_author_phone 608-263-4694
_publ_contact_author_fax 608-262-0381
_publ_contact_author_email iguzei@chem.wisc.edu
_publ_contact_letter
;
Please consider this CIF submission
for publication in
;
# 2. TITLE AND AUTHOR LIST
_publ_section_title
;
Title (type here to add)
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loop_
_publ_author_name
_publ_author_address
C.J.Czerwinski
;
Department of Chemistry
University of Wisconsin-La Crosse
1725 State Street
La Crosse, WI 54601
USA
;
I.A.Guzei
;
Department of Chemistry
University of Wisconsin-Madison
1101 University Ave
Madison, WI 53706
USA
;
K.M.Riggle
;
Department of Chemistry
University of Wisconsin-La Crosse
1725 State Street
La Crosse, WI 54601
USA
;
J.R.Schroeder
;
Department of Chemistry
University of Wisconsin-La Crosse
1725 State Street
La Crosse, WI 54601
USA
;
L.C.Spencer
;
Department of Chemistry
University of Wisconsin-Madison
1101 University Ave
Madison, WI 53706
USA
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_publ_section_synopsis .
_publ_section_abstract
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(type here to add abstract)
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_publ_section_comment
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(type here to add)
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_publ_section_references
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Allen, F. H. (2002). Acta Cryst. B58, 380--388.
Bruker-AXS. (2000). SMART (Version 5.622). Bruker-AXS Inc., Madison, WI,
USA.
Bruker-AXS. (2007). SADABS, SAINTPLUS, SHELXTL. Bruker-AXS
Inc., Madison, WI, USA.
Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F.,
McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58,
389--397.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97,
1358--1367.
Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A.,
Cheeseman, J. R., Montgomery, J. A. Jr, Vreven, T., Kudin, K. N., Burant, J.
C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., et
al. (2004). Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford, CT,
USA.
Guzei, I. A. (2007). In-house Crystallographic Programs, Molecular Structure
Laboratory, University of Wisconsin-Madison, Madison, WI, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
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_publ_section_acknowledgements
;
We thank the National Science Foundation for financial support.
The manuscript was prepared with the beta test version 1.0.2. of program
publCIF to be released by the IUCr and Ilia A. Guzei's program
modiCIFer.
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_publ_section_figure_captions
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Figure 1. Molecular structure of (I). The thermal ellipsoids are shown at 50%
probability level.
;
_publ_section_exptl_prep
;
;
_publ_section_exptl_refinement
;
All H-atoms attached to carbon atoms were placed in idealized locations and
refined as riding with appropriate thermal displacement coefficients
U~iso~(H) = 1.2 or 1.5 times U~eq~(bearing atom).
;
# File processed with modiCIFer (v.3-27-2007). I.A.Guzei, UW-Madison.
#5. data
data_cze002
_database_code_depnum_ccdc_archive 'CCDC 778546'
#TrackingRef '- czepaper_revised.cif'
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C15 H11 Cr N O3'
_chemical_formula_sum 'C15 H11 Cr N O3'
_chemical_formula_weight 305.25
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr 0.3209 0.6236 '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 1 21/c 1 '
_symmetry_space_group_name_Hall '-P 2ybc '
_symmetry_int_tables_number 14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 7.2106(9)
_cell_length_b 28.140(3)
_cell_length_c 7.1535(8)
_cell_angle_alpha 90.00
_cell_angle_beta 118.175(2)
_cell_angle_gamma 90.00
_cell_volume 1279.5(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 7505
_cell_measurement_theta_min 2.90
_cell_measurement_theta_max 26.47
_exptl_crystal_description block
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.37
_exptl_crystal_size_mid 0.36
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.585
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 624
_exptl_absorpt_coefficient_mu 0.899
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS (Bruker-AXS, 2007)
;
_exptl_absorpt_correction_T_min 0.7320
_exptl_absorpt_correction_T_max 0.8406
_exptl_special_details ?
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD-1000 area detector'
_diffrn_measurement_method '0.30\\% \\w and 0.4 \\% \\f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 10331
_diffrn_reflns_av_R_equivalents 0.0254
_diffrn_reflns_av_sigmaI/netI 0.0207
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -35
_diffrn_reflns_limit_k_max 34
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_theta_min 2.90
_diffrn_reflns_theta_max 26.47
_reflns_number_total 2615
_reflns_number_gt 2511
_reflns_threshold_expression I>2\\s(I)
_computing_data_collection 'SMART Ver. 5.622 (Bruker-AXS, 2000)'
_computing_cell_refinement 'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_reduction 'SAINT Ver. 7.24A'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement SHELXTL
_computing_molecular_graphics SHELXTL
_computing_publication_material 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.
;
_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\^)+(0.0439P)\^2\^+0.9379P]
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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2615
_refine_ls_number_parameters 187
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0304
_refine_ls_R_factor_gt 0.0292
_refine_ls_wR_factor_ref 0.0813
_refine_ls_wR_factor_gt 0.0804
_refine_ls_goodness_of_fit_ref 1.060
_refine_ls_restrained_S_all 1.060
_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
Cr1 Cr 0.75861(4) 0.086012(9) 0.87185(4) 0.01375(10) Uani 1 1 d . . .
O1 O 0.5216(2) 0.13285(5) 1.0708(2) 0.0257(3) Uani 1 1 d . . .
O2 O 0.4890(3) -0.00114(5) 0.7780(2) 0.0384(4) Uani 1 1 d . . .
O3 O 1.0483(2) 0.04408(5) 1.2969(2) 0.0288(3) Uani 1 1 d . . .
N1 N 0.5922(3) 0.22941(6) 0.4006(3) 0.0216(3) Uani 1 1 d . . .
H1A H 0.675(4) 0.2104(8) 0.403(4) 0.026 Uiso 1 1 d . . .
H1B H 0.560(4) 0.2475(9) 0.300(4) 0.026 Uiso 1 1 d . . .
C1 C 0.6365(2) 0.13884(5) 0.6084(2) 0.0145(3) Uani 1 1 d . . .
C2 C 0.6512(3) 0.09404(6) 0.5287(3) 0.0164(3) Uani 1 1 d . . .
H2 H 0.5306 0.0808 0.4126 0.020 Uiso 1 1 calc R . .
C3 C 0.8432(3) 0.06838(6) 0.6192(3) 0.0191(3) Uani 1 1 d . . .
H3 H 0.8512 0.0384 0.5622 0.023 Uiso 1 1 calc R . .
C4 C 1.0209(3) 0.08722(6) 0.7927(3) 0.0202(4) Uani 1 1 d . . .
H4 H 1.1491 0.0699 0.8543 0.024 Uiso 1 1 calc R . .
C5 C 1.0098(3) 0.13208(6) 0.8764(3) 0.0183(3) Uani 1 1 d . . .
H5 H 1.1306 0.1450 0.9934 0.022 Uiso 1 1 calc R . .
C6 C 0.8195(2) 0.15751(6) 0.7857(2) 0.0157(3) Uani 1 1 d . . .
H6 H 0.8123 0.1875 0.8429 0.019 Uiso 1 1 calc R . .
C7 C 0.4332(2) 0.16540(6) 0.5090(2) 0.0149(3) Uani 1 1 d . . .
C8 C 0.4169(3) 0.20885(6) 0.4042(2) 0.0164(3) Uani 1 1 d . . .
C9 C 0.2226(3) 0.23223(6) 0.3066(3) 0.0195(3) Uani 1 1 d . . .
H9 H 0.2116 0.2622 0.2408 0.023 Uiso 1 1 calc R . .
C10 C 0.0466(3) 0.21231(6) 0.3046(3) 0.0201(3) Uani 1 1 d . . .
H10 H -0.0847 0.2284 0.2351 0.024 Uiso 1 1 calc R . .
C11 C 0.0601(3) 0.16894(6) 0.4036(3) 0.0192(3) Uani 1 1 d . . .
H11 H -0.0612 0.1551 0.4012 0.023 Uiso 1 1 calc R . .
C12 C 0.2537(3) 0.14620(6) 0.5060(2) 0.0169(3) Uani 1 1 d . . .
H12 H 0.2640 0.1168 0.5758 0.020 Uiso 1 1 calc R . .
C13 C 0.6119(3) 0.11411(6) 0.9946(3) 0.0177(3) Uani 1 1 d . . .
C14 C 0.5925(3) 0.03246(6) 0.8143(3) 0.0236(4) Uani 1 1 d . . .
C15 C 0.9376(3) 0.06011(6) 1.1335(3) 0.0196(3) Uani 1 1 d . . .
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
Cr1 0.01652(16) 0.01266(16) 0.01189(16) 0.00068(8) 0.00657(12) 0.00027(9)
O1 0.0219(6) 0.0373(7) 0.0196(6) -0.0010(5) 0.0111(5) 0.0050(5)
O2 0.0597(10) 0.0304(8) 0.0312(8) -0.0097(6) 0.0264(7) -0.0250(7)
O3 0.0373(8) 0.0232(6) 0.0191(6) 0.0050(5) 0.0078(6) 0.0085(6)
N1 0.0219(8) 0.0177(7) 0.0230(8) 0.0067(6) 0.0087(6) -0.0004(6)
C1 0.0177(8) 0.0141(7) 0.0128(7) 0.0022(6) 0.0081(6) -0.0006(6)
C2 0.0202(8) 0.0165(8) 0.0131(8) 0.0006(6) 0.0082(6) -0.0010(6)
C3 0.0280(9) 0.0167(8) 0.0177(8) 0.0026(6) 0.0149(7) 0.0045(6)
C4 0.0202(9) 0.0219(9) 0.0214(9) 0.0064(6) 0.0123(7) 0.0064(6)
C5 0.0162(8) 0.0209(8) 0.0172(8) 0.0030(6) 0.0073(6) -0.0010(6)
C6 0.0176(8) 0.0142(7) 0.0157(8) 0.0013(6) 0.0082(6) -0.0005(6)
C7 0.0176(8) 0.0142(7) 0.0106(7) -0.0011(6) 0.0047(6) 0.0010(6)
C8 0.0202(8) 0.0156(8) 0.0114(7) -0.0023(6) 0.0059(6) -0.0017(6)
C9 0.0261(9) 0.0169(8) 0.0128(7) 0.0021(6) 0.0068(7) 0.0033(6)
C10 0.0191(8) 0.0252(9) 0.0123(7) -0.0009(6) 0.0044(6) 0.0061(7)
C11 0.0166(8) 0.0244(9) 0.0152(8) -0.0030(6) 0.0064(6) -0.0010(6)
C12 0.0194(8) 0.0172(8) 0.0129(7) -0.0007(6) 0.0066(6) -0.0006(6)
C13 0.0169(8) 0.0200(8) 0.0120(7) 0.0032(6) 0.0035(6) -0.0006(6)
C14 0.0331(10) 0.0237(9) 0.0153(8) -0.0021(7) 0.0125(7) -0.0042(7)
C15 0.0243(8) 0.0155(8) 0.0196(8) 0.0000(6) 0.0110(7) 0.0027(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
Cr1 C13 1.8422(18) . yes
Cr1 C14 1.8463(18) . yes
Cr1 C15 1.8488(18) . yes
Cr1 C6 2.2084(16) . yes
Cr1 C2 2.2091(16) . yes
Cr1 C5 2.2152(17) . yes
Cr1 C4 2.2156(18) . yes
Cr1 C3 2.2190(16) . yes
Cr1 C1 2.2295(15) . yes
O1 C13 1.155(2) . ?
O2 C14 1.156(2) . ?
O3 C15 1.152(2) . ?
N1 C8 1.402(2) . ?
N1 H1A 0.80(2) . ?
N1 H1B 0.82(3) . ?
C1 C2 1.408(2) . ?
C1 C6 1.430(2) . ?
C1 C7 1.493(2) . ?
C2 C3 1.418(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.415(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.393(2) . ?
C7 C8 1.410(2) . ?
C8 C9 1.400(2) . ?
C9 C10 1.381(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
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
C13 Cr1 C14 89.92(8) . . yes
C13 Cr1 C15 88.29(7) . . yes
C14 Cr1 C15 88.46(8) . . yes
C13 Cr1 C6 88.66(7) . . yes
C14 Cr1 C6 151.03(7) . . yes
C15 Cr1 C6 120.40(7) . . yes
C13 Cr1 C2 120.44(7) . . yes
C14 Cr1 C2 89.16(7) . . yes
C15 Cr1 C2 151.16(7) . . yes
C6 Cr1 C2 66.94(6) . . yes
C13 Cr1 C5 113.05(7) . . yes
C14 Cr1 C5 157.02(7) . . yes
C15 Cr1 C5 92.34(7) . . yes
C6 Cr1 C5 37.05(6) . . yes
C2 Cr1 C5 79.15(6) . . yes
C13 Cr1 C4 150.10(7) . . yes
C14 Cr1 C4 119.83(7) . . yes
C15 Cr1 C4 89.58(7) . . yes
C6 Cr1 C4 66.95(6) . . yes
C2 Cr1 C4 66.95(6) . . yes
C5 Cr1 C4 37.26(6) . . yes
C13 Cr1 C3 157.63(7) . . yes
C14 Cr1 C3 91.98(7) . . yes
C15 Cr1 C3 114.04(7) . . yes
C6 Cr1 C3 78.99(6) . . yes
C2 Cr1 C3 37.35(6) . . yes
C5 Cr1 C3 66.77(6) . . yes
C4 Cr1 C3 36.82(7) . . yes
C13 Cr1 C1 91.75(7) . . yes
C14 Cr1 C1 113.58(7) . . yes
C15 Cr1 C1 157.95(7) . . yes
C6 Cr1 C1 37.59(6) . . yes
C2 Cr1 C1 36.98(6) . . yes
C5 Cr1 C1 67.41(6) . . yes
C4 Cr1 C1 79.49(6) . . yes
C3 Cr1 C1 67.12(6) . . yes
C8 N1 H1A 113.4(17) . . ?
C8 N1 H1B 112.7(16) . . ?
H1A N1 H1B 110(2) . . ?
C2 C1 C6 118.30(15) . . ?
C2 C1 C7 120.00(14) . . ?
C6 C1 C7 121.70(14) . . ?
C2 C1 Cr1 70.72(9) . . ?
C6 C1 Cr1 70.40(9) . . ?
C7 C1 Cr1 130.02(11) . . ?
C1 C2 C3 120.98(15) . . ?
C1 C2 Cr1 72.30(9) . . ?
C3 C2 Cr1 71.70(9) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
Cr1 C2 H2 128.8 . . ?
C4 C3 C2 119.96(15) . . ?
C4 C3 Cr1 71.46(10) . . ?
C2 C3 Cr1 70.94(9) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
Cr1 C3 H3 130.1 . . ?
C3 C4 C5 120.11(15) . . ?
C3 C4 Cr1 71.72(10) . . ?
C5 C4 Cr1 71.36(10) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
Cr1 C4 H4 129.4 . . ?
C6 C5 C4 119.77(15) . . ?
C6 C5 Cr1 71.21(9) . . ?
C4 C5 Cr1 71.39(10) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
Cr1 C5 H5 129.7 . . ?
C5 C6 C1 120.87(15) . . ?
C5 C6 Cr1 71.74(9) . . ?
C1 C6 Cr1 72.01(9) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
Cr1 C6 H6 129.1 . . ?
C12 C7 C8 118.97(15) . . ?
C12 C7 C1 120.63(14) . . ?
C8 C7 C1 120.27(14) . . ?
C9 C8 N1 119.71(15) . . ?
C9 C8 C7 119.07(15) . . ?
N1 C8 C7 121.20(15) . . ?
C10 C9 C8 120.83(15) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.51(15) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 118.94(16) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C7 121.63(15) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
O1 C13 Cr1 178.24(15) . . ?
O2 C14 Cr1 179.77(18) . . ?
O3 C15 Cr1 179.60(18) . . ?
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
C13 Cr1 C1 C2 -143.35(10) . . . . ?
C14 Cr1 C1 C2 -52.67(12) . . . . ?
C15 Cr1 C1 C2 126.89(18) . . . . ?
C6 Cr1 C1 C2 131.12(14) . . . . ?
C5 Cr1 C1 C2 102.34(11) . . . . ?
C4 Cr1 C1 C2 65.43(10) . . . . ?
C3 Cr1 C1 C2 29.09(10) . . . . ?
C13 Cr1 C1 C6 85.54(10) . . . . ?
C14 Cr1 C1 C6 176.21(10) . . . . ?
C15 Cr1 C1 C6 -4.2(2) . . . . ?
C2 Cr1 C1 C6 -131.12(14) . . . . ?
C5 Cr1 C1 C6 -28.77(9) . . . . ?
C4 Cr1 C1 C6 -65.68(10) . . . . ?
C3 Cr1 C1 C6 -102.03(10) . . . . ?
C13 Cr1 C1 C7 -29.90(15) . . . . ?
C14 Cr1 C1 C7 60.78(16) . . . . ?
C15 Cr1 C1 C7 -119.65(19) . . . . ?
C6 Cr1 C1 C7 -115.43(18) . . . . ?
C2 Cr1 C1 C7 113.45(18) . . . . ?
C5 Cr1 C1 C7 -144.20(16) . . . . ?
C4 Cr1 C1 C7 178.89(15) . . . . ?
C3 Cr1 C1 C7 142.54(16) . . . . ?
C6 C1 C2 C3 -1.1(2) . . . . ?
C7 C1 C2 C3 179.38(15) . . . . ?
Cr1 C1 C2 C3 -54.83(14) . . . . ?
C6 C1 C2 Cr1 53.71(13) . . . . ?
C7 C1 C2 Cr1 -125.78(14) . . . . ?
C13 Cr1 C2 C1 43.80(12) . . . . ?
C14 Cr1 C2 C1 133.21(11) . . . . ?
C15 Cr1 C2 C1 -141.50(14) . . . . ?
C6 Cr1 C2 C1 -29.97(9) . . . . ?
C5 Cr1 C2 C1 -66.68(10) . . . . ?
C4 Cr1 C2 C1 -103.63(10) . . . . ?
C3 Cr1 C2 C1 -132.42(15) . . . . ?
C13 Cr1 C2 C3 176.22(10) . . . . ?
C14 Cr1 C2 C3 -94.37(11) . . . . ?
C15 Cr1 C2 C3 -9.08(19) . . . . ?
C6 Cr1 C2 C3 102.46(11) . . . . ?
C5 Cr1 C2 C3 65.74(10) . . . . ?
C4 Cr1 C2 C3 28.79(10) . . . . ?
C1 Cr1 C2 C3 132.42(15) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
Cr1 C2 C3 C4 -54.02(14) . . . . ?
C1 C2 C3 Cr1 55.11(14) . . . . ?
C13 Cr1 C3 C4 123.72(18) . . . . ?
C14 Cr1 C3 C4 -141.67(11) . . . . ?
C15 Cr1 C3 C4 -52.47(12) . . . . ?
C6 Cr1 C3 C4 66.07(10) . . . . ?
C2 Cr1 C3 C4 132.31(15) . . . . ?
C5 Cr1 C3 C4 29.32(9) . . . . ?
C1 Cr1 C3 C4 103.50(11) . . . . ?
C13 Cr1 C3 C2 -8.6(2) . . . . ?
C14 Cr1 C3 C2 86.02(11) . . . . ?
C15 Cr1 C3 C2 175.22(10) . . . . ?
C6 Cr1 C3 C2 -66.24(10) . . . . ?
C5 Cr1 C3 C2 -102.99(11) . . . . ?
C4 Cr1 C3 C2 -132.31(15) . . . . ?
C1 Cr1 C3 C2 -28.81(9) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
Cr1 C3 C4 C5 -54.50(14) . . . . ?
C2 C3 C4 Cr1 53.78(14) . . . . ?
C13 Cr1 C4 C3 -140.57(13) . . . . ?
C14 Cr1 C4 C3 45.60(12) . . . . ?
C15 Cr1 C4 C3 133.59(11) . . . . ?
C6 Cr1 C4 C3 -102.83(11) . . . . ?
C2 Cr1 C4 C3 -29.18(9) . . . . ?
C5 Cr1 C4 C3 -131.99(14) . . . . ?
C1 Cr1 C4 C3 -65.66(10) . . . . ?
C13 Cr1 C4 C5 -8.58(18) . . . . ?
C14 Cr1 C4 C5 177.59(10) . . . . ?
C15 Cr1 C4 C5 -94.42(11) . . . . ?
C6 Cr1 C4 C5 29.16(9) . . . . ?
C2 Cr1 C4 C5 102.80(11) . . . . ?
C3 Cr1 C4 C5 131.99(14) . . . . ?
C1 Cr1 C4 C5 66.33(10) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
Cr1 C4 C5 C6 -54.25(14) . . . . ?
C3 C4 C5 Cr1 54.67(14) . . . . ?
C13 Cr1 C5 C6 -52.72(11) . . . . ?
C14 Cr1 C5 C6 126.56(18) . . . . ?
C15 Cr1 C5 C6 -141.85(10) . . . . ?
C2 Cr1 C5 C6 65.91(10) . . . . ?
C4 Cr1 C5 C6 131.92(14) . . . . ?
C3 Cr1 C5 C6 102.92(11) . . . . ?
C1 Cr1 C5 C6 29.16(9) . . . . ?
C13 Cr1 C5 C4 175.36(10) . . . . ?
C14 Cr1 C5 C4 -5.4(2) . . . . ?
C15 Cr1 C5 C4 86.23(11) . . . . ?
C6 Cr1 C5 C4 -131.92(14) . . . . ?
C2 Cr1 C5 C4 -66.01(10) . . . . ?
C3 Cr1 C5 C4 -29.00(10) . . . . ?
C1 Cr1 C5 C4 -102.75(11) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
Cr1 C5 C6 C1 -54.81(13) . . . . ?
C4 C5 C6 Cr1 54.33(14) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C7 C1 C6 C5 -179.69(14) . . . . ?
Cr1 C1 C6 C5 54.69(14) . . . . ?
C2 C1 C6 Cr1 -53.87(13) . . . . ?
C7 C1 C6 Cr1 125.62(14) . . . . ?
C13 Cr1 C6 C5 132.92(10) . . . . ?
C14 Cr1 C6 C5 -139.65(15) . . . . ?
C15 Cr1 C6 C5 45.69(12) . . . . ?
C2 Cr1 C6 C5 -102.97(11) . . . . ?
C4 Cr1 C6 C5 -29.31(10) . . . . ?
C3 Cr1 C6 C5 -65.84(10) . . . . ?
C1 Cr1 C6 C5 -132.48(14) . . . . ?
C13 Cr1 C6 C1 -94.60(10) . . . . ?
C14 Cr1 C6 C1 -7.18(19) . . . . ?
C15 Cr1 C6 C1 178.16(10) . . . . ?
C2 Cr1 C6 C1 29.51(9) . . . . ?
C5 Cr1 C6 C1 132.48(14) . . . . ?
C4 Cr1 C6 C1 103.16(10) . . . . ?
C3 Cr1 C6 C1 66.63(10) . . . . ?
C2 C1 C7 C12 60.9(2) . . . . ?
C6 C1 C7 C12 -118.53(17) . . . . ?
Cr1 C1 C7 C12 -28.3(2) . . . . ?
C2 C1 C7 C8 -114.74(17) . . . . ?
C6 C1 C7 C8 65.8(2) . . . . ?
Cr1 C1 C7 C8 156.01(12) . . . . ?
C12 C7 C8 C9 2.2(2) . . . . ?
C1 C7 C8 C9 177.94(14) . . . . ?
C12 C7 C8 N1 -179.32(15) . . . . ?
C1 C7 C8 N1 -3.6(2) . . . . ?
N1 C8 C9 C10 178.83(16) . . . . ?
C7 C8 C9 C10 -2.7(2) . . . . ?
C8 C9 C10 C11 1.3(2) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C10 C11 C12 C7 -1.0(2) . . . . ?
C8 C7 C12 C11 -0.4(2) . . . . ?
C1 C7 C12 C11 -176.13(14) . . . . ?
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full 26.47
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max 0.410
_refine_diff_density_min -0.307
_refine_diff_density_rms 0.061
# File processed with modiCIFer (v.3-27-2007). I.A.Guzei, UW-Madison.
#6. data
data_cze006
_database_code_depnum_ccdc_archive 'CCDC 778547'
#TrackingRef '- czepaper_revised.cif'
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C15 H11 Cr N O3'
_chemical_formula_sum 'C15 H11 Cr N O3'
_chemical_formula_weight 305.25
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr 0.3209 0.6236 '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 b c a '
_symmetry_space_group_name_Hall '-P 2ac 2ab '
_symmetry_int_tables_number 61
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'
'-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 7.5427(5)
_cell_length_b 12.7303(9)
_cell_length_c 26.7851(19)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2571.9(3)
_cell_formula_units_Z 8
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 7826
_cell_measurement_theta_min 3.04
_cell_measurement_theta_max 26.39
_exptl_crystal_description block
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.47
_exptl_crystal_size_mid 0.42
_exptl_crystal_size_min 0.19
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.577
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1248
_exptl_absorpt_coefficient_mu 0.895
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS (Bruker-AXS, 2007)
;
_exptl_absorpt_correction_T_min 0.6785
_exptl_absorpt_correction_T_max 0.8484
_exptl_special_details ?
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD-1000 area detector'
_diffrn_measurement_method '0.30\\% \\w and 0.4 \\% \\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 19756
_diffrn_reflns_av_R_equivalents 0.0288
_diffrn_reflns_av_sigmaI/netI 0.0165
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -33
_diffrn_reflns_limit_l_max 33
_diffrn_reflns_theta_min 3.04
_diffrn_reflns_theta_max 26.39
_reflns_number_total 2629
_reflns_number_gt 2374
_reflns_threshold_expression I>2\\s(I)
_computing_data_collection 'SMART Ver. 5.622 (Bruker-AXS, 2000)'
_computing_cell_refinement 'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_reduction 'SAINT Ver. 7.24A'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement SHELXTL
_computing_molecular_graphics SHELXTL
_computing_publication_material 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.
;
_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\^)+(0.0644P)\^2\^+1.9111P]
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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2629
_refine_ls_number_parameters 187
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0391
_refine_ls_R_factor_gt 0.0350
_refine_ls_wR_factor_ref 0.1011
_refine_ls_wR_factor_gt 0.0980
_refine_ls_goodness_of_fit_ref 1.033
_refine_ls_restrained_S_all 1.033
_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
Cr Cr 1.17961(4) 0.69978(2) 0.402581(11) 0.01513(13) Uani 1 1 d . . .
O1 O 1.5188(2) 0.81354(12) 0.42281(6) 0.0299(4) Uani 1 1 d . . .
O2 O 1.1949(2) 0.81222(12) 0.30438(6) 0.0292(4) Uani 1 1 d . . .
O3 O 0.9530(2) 0.86963(11) 0.44660(6) 0.0297(4) Uani 1 1 d . . .
N N 0.7954(2) 0.61403(14) 0.45480(7) 0.0240(4) Uani 1 1 d D . .
H1N H 0.708(3) 0.6409(19) 0.4336(8) 0.029 Uiso 1 1 d D . .
H2N H 0.802(3) 0.6500(18) 0.4852(7) 0.029 Uiso 1 1 d D . .
C1 C 0.9575(3) 0.59404(14) 0.43397(7) 0.0181(4) Uani 1 1 d . . .
C2 C 1.1114(3) 0.59006(14) 0.46485(7) 0.0202(4) Uani 1 1 d . . .
H2 H 1.1017 0.6067 0.4993 0.024 Uiso 1 1 calc R . .
C3 C 1.2762(3) 0.56207(15) 0.44511(7) 0.0215(4) Uani 1 1 d . . .
H3 H 1.3764 0.5580 0.4665 0.026 Uiso 1 1 calc R . .
C4 C 1.2956(3) 0.53971(15) 0.39380(8) 0.0209(4) Uani 1 1 d . . .
H4 H 1.4071 0.5191 0.3805 0.025 Uiso 1 1 calc R . .
C5 C 1.1467(3) 0.54854(14) 0.36292(7) 0.0189(4) Uani 1 1 d . . .
H5 H 1.1594 0.5353 0.3282 0.023 Uiso 1 1 calc R . .
C6 C 0.9770(3) 0.57671(13) 0.38178(7) 0.0170(4) Uani 1 1 d . . .
C7 C 0.8230(2) 0.58139(15) 0.34704(7) 0.0181(4) Uani 1 1 d . . .
C8 C 0.7630(3) 0.48895(16) 0.32463(8) 0.0254(4) Uani 1 1 d . . .
H8 H 0.8175 0.4239 0.3327 0.030 Uiso 1 1 calc R . .
C9 C 0.6240(3) 0.4915(2) 0.29066(8) 0.0323(5) Uani 1 1 d . . .
H9 H 0.5841 0.4284 0.2754 0.039 Uiso 1 1 calc R . .
C10 C 0.5437(3) 0.5864(2) 0.27898(8) 0.0332(5) Uani 1 1 d . . .
H10 H 0.4486 0.5880 0.2558 0.040 Uiso 1 1 calc R . .
C11 C 0.6013(3) 0.67851(19) 0.30094(8) 0.0283(5) Uani 1 1 d . . .
H11 H 0.5460 0.7433 0.2928 0.034 Uiso 1 1 calc R . .
C12 C 0.7409(3) 0.67592(16) 0.33499(7) 0.0224(4) Uani 1 1 d . . .
H12 H 0.7803 0.7392 0.3501 0.027 Uiso 1 1 calc R . .
C13 C 1.3858(3) 0.76977(16) 0.41620(7) 0.0212(4) Uani 1 1 d . . .
C14 C 1.1861(2) 0.76812(16) 0.34190(7) 0.0191(4) Uani 1 1 d . . .
C15 C 1.0443(3) 0.80629(14) 0.42919(7) 0.0195(4) Uani 1 1 d . . .
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
Cr 0.0183(2) 0.0130(2) 0.01408(19) 0.00066(10) -0.00136(11) 0.00051(11)
O1 0.0239(8) 0.0332(8) 0.0327(8) -0.0059(7) -0.0065(7) -0.0055(6)
O2 0.0383(9) 0.0284(8) 0.0209(8) 0.0075(6) 0.0012(6) 0.0060(6)
O3 0.0304(8) 0.0200(7) 0.0387(9) -0.0054(6) 0.0129(7) -0.0023(6)
N 0.0246(9) 0.0263(9) 0.0211(9) 0.0010(7) 0.0016(7) -0.0015(7)
C1 0.0250(10) 0.0108(8) 0.0186(9) 0.0023(7) 0.0033(7) -0.0024(7)
C2 0.0304(11) 0.0152(9) 0.0149(9) 0.0042(7) -0.0018(8) -0.0011(8)
C3 0.0268(10) 0.0159(9) 0.0217(10) 0.0040(7) -0.0048(8) 0.0028(8)
C4 0.0238(10) 0.0144(9) 0.0245(10) 0.0013(7) 0.0000(8) 0.0047(7)
C5 0.0249(10) 0.0134(9) 0.0185(9) -0.0007(7) -0.0001(7) 0.0018(7)
C6 0.0231(9) 0.0096(8) 0.0184(9) 0.0014(7) -0.0004(7) -0.0009(7)
C7 0.0188(9) 0.0203(10) 0.0150(9) -0.0004(7) 0.0038(7) -0.0036(7)
C8 0.0281(10) 0.0238(10) 0.0242(10) -0.0030(8) 0.0035(9) -0.0075(8)
C9 0.0296(11) 0.0424(13) 0.0249(10) -0.0086(9) 0.0040(9) -0.0181(10)
C10 0.0189(10) 0.0624(16) 0.0181(10) -0.0011(10) -0.0005(8) -0.0100(10)
C11 0.0211(10) 0.0424(12) 0.0213(10) 0.0025(9) -0.0008(8) 0.0021(9)
C12 0.0216(10) 0.0243(10) 0.0213(10) -0.0005(8) -0.0011(8) -0.0002(8)
C13 0.0254(11) 0.0208(9) 0.0173(9) -0.0007(8) -0.0028(8) 0.0040(8)
C14 0.0203(10) 0.0163(9) 0.0208(10) -0.0025(8) -0.0018(7) 0.0022(7)
C15 0.0212(10) 0.0162(9) 0.0211(9) 0.0004(7) 0.0020(8) -0.0052(7)
_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
Cr C13 1.829(2) . yes
Cr C15 1.8406(19) . yes
Cr C14 1.844(2) . yes
Cr C5 2.2129(19) . yes
Cr C3 2.2140(19) . yes
Cr C4 2.230(2) . yes
Cr C2 2.2356(18) . yes
Cr C6 2.2582(18) . yes
Cr C1 2.3077(18) . yes
O1 C13 1.161(3) . ?
O2 C14 1.153(3) . ?
O3 C15 1.158(2) . ?
N C1 1.368(3) . ?
N H1N 0.935(17) . ?
N H2N 0.936(17) . ?
C1 C6 1.423(3) . ?
C1 C2 1.426(3) . ?
C2 C3 1.397(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.411(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.422(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.490(3) . ?
C7 C12 1.391(3) . ?
C7 C8 1.397(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
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
C13 Cr C15 92.03(8) . . yes
C13 Cr C14 85.60(9) . . yes
C15 Cr C14 90.49(8) . . yes
C13 Cr C5 127.94(8) . . yes
C15 Cr C5 139.87(8) . . yes
C14 Cr C5 89.44(8) . . yes
C13 Cr C3 90.19(8) . . yes
C15 Cr C3 124.51(8) . . yes
C14 Cr C3 144.91(8) . . yes
C5 Cr C3 66.11(7) . . yes
C13 Cr C4 97.62(8) . . yes
C15 Cr C4 158.66(8) . . yes
C14 Cr C4 109.13(8) . . yes
C5 Cr C4 36.71(7) . . yes
C3 Cr C4 37.02(7) . . yes
C13 Cr C2 110.57(8) . . yes
C15 Cr C2 92.50(8) . . yes
C14 Cr C2 163.42(8) . . yes
C5 Cr C2 77.81(7) . . yes
C3 Cr C2 36.60(8) . . yes
C4 Cr C2 66.30(7) . . yes
C13 Cr C6 164.25(8) . . yes
C15 Cr C6 103.38(8) . . yes
C14 Cr C6 97.35(8) . . yes
C5 Cr C6 37.07(7) . . yes
C3 Cr C6 78.48(7) . . yes
C4 Cr C6 66.76(7) . . yes
C2 Cr C6 66.10(7) . . yes
C13 Cr C1 145.97(8) . . yes
C15 Cr C1 83.46(7) . . yes
C14 Cr C1 127.99(8) . . yes
C5 Cr C1 65.54(7) . . yes
C3 Cr C1 65.77(7) . . yes
C4 Cr C1 77.88(7) . . yes
C2 Cr C1 36.55(7) . . yes
C6 Cr C1 36.29(7) . . yes
C1 N H1N 116.9(15) . . ?
C1 N H2N 113.6(15) . . ?
H1N N H2N 113(2) . . ?
N C1 C6 121.49(17) . . ?
N C1 C2 119.82(17) . . ?
C6 C1 C2 118.69(17) . . ?
N C1 Cr 133.55(14) . . ?
C6 C1 Cr 69.96(10) . . ?
C2 C1 Cr 68.98(10) . . ?
C3 C2 C1 120.91(17) . . ?
C3 C2 Cr 70.86(11) . . ?
C1 C2 Cr 74.48(10) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
Cr C2 H2 127.1 . . ?
C2 C3 C4 120.81(18) . . ?
C2 C3 Cr 72.54(11) . . ?
C4 C3 Cr 72.10(11) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
Cr C3 H3 127.9 . . ?
C5 C4 C3 118.46(19) . . ?
C5 C4 Cr 70.98(11) . . ?
C3 C4 Cr 70.88(11) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
Cr C4 H4 129.7 . . ?
C4 C5 C6 122.16(18) . . ?
C4 C5 Cr 72.30(11) . . ?
C6 C5 Cr 73.20(10) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
Cr C5 H5 127.8 . . ?
C5 C6 C1 118.79(17) . . ?
C5 C6 C7 119.33(16) . . ?
C1 C6 C7 121.79(17) . . ?
C5 C6 Cr 69.74(11) . . ?
C1 C6 Cr 73.75(10) . . ?
C7 C6 Cr 130.84(12) . . ?
C12 C7 C8 118.99(18) . . ?
C12 C7 C6 121.78(17) . . ?
C8 C7 C6 119.19(18) . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.58(19) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O1 C13 Cr 177.16(18) . . ?
O2 C14 Cr 177.96(18) . . ?
O3 C15 Cr 176.62(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
C13 Cr C1 N 92.4(2) . . . . ?
C15 Cr C1 N 8.48(19) . . . . ?
C14 Cr C1 N -77.0(2) . . . . ?
C5 Cr C1 N -145.4(2) . . . . ?
C3 Cr C1 N 141.1(2) . . . . ?
C4 Cr C1 N 178.1(2) . . . . ?
C2 Cr C1 N 111.7(2) . . . . ?
C6 Cr C1 N -114.9(2) . . . . ?
C13 Cr C1 C6 -152.74(14) . . . . ?
C15 Cr C1 C6 123.35(12) . . . . ?
C14 Cr C1 C6 37.85(14) . . . . ?
C5 Cr C1 C6 -30.50(11) . . . . ?
C3 Cr C1 C6 -104.05(12) . . . . ?
C4 Cr C1 C6 -67.07(11) . . . . ?
C2 Cr C1 C6 -133.45(16) . . . . ?
C13 Cr C1 C2 -19.29(19) . . . . ?
C15 Cr C1 C2 -103.21(12) . . . . ?
C14 Cr C1 C2 171.30(12) . . . . ?
C5 Cr C1 C2 102.95(12) . . . . ?
C3 Cr C1 C2 29.39(11) . . . . ?
C4 Cr C1 C2 66.37(12) . . . . ?
C6 Cr C1 C2 133.45(16) . . . . ?
N C1 C2 C3 175.17(18) . . . . ?
C6 C1 C2 C3 -4.7(3) . . . . ?
Cr C1 C2 C3 -55.75(16) . . . . ?
N C1 C2 Cr -129.08(17) . . . . ?
C6 C1 C2 Cr 51.03(14) . . . . ?
C13 Cr C2 C3 -60.04(14) . . . . ?
C15 Cr C2 C3 -153.15(13) . . . . ?
C14 Cr C2 C3 106.7(3) . . . . ?
C5 Cr C2 C3 66.17(12) . . . . ?
C4 Cr C2 C3 29.38(12) . . . . ?
C6 Cr C2 C3 103.31(13) . . . . ?
C1 Cr C2 C3 131.35(17) . . . . ?
C13 Cr C2 C1 168.61(11) . . . . ?
C15 Cr C2 C1 75.50(12) . . . . ?
C14 Cr C2 C1 -24.7(3) . . . . ?
C5 Cr C2 C1 -65.18(11) . . . . ?
C3 Cr C2 C1 -131.35(17) . . . . ?
C4 Cr C2 C1 -101.96(12) . . . . ?
C6 Cr C2 C1 -28.04(10) . . . . ?
C1 C2 C3 C4 1.7(3) . . . . ?
Cr C2 C3 C4 -55.76(17) . . . . ?
C1 C2 C3 Cr 57.46(16) . . . . ?
C13 Cr C3 C2 125.79(13) . . . . ?
C15 Cr C3 C2 33.20(15) . . . . ?
C14 Cr C3 C2 -151.60(14) . . . . ?
C5 Cr C3 C2 -102.06(13) . . . . ?
C4 Cr C3 C2 -131.74(18) . . . . ?
C6 Cr C3 C2 -65.23(12) . . . . ?
C1 Cr C3 C2 -29.35(11) . . . . ?
C13 Cr C3 C4 -102.47(13) . . . . ?
C15 Cr C3 C4 164.94(12) . . . . ?
C14 Cr C3 C4 -19.9(2) . . . . ?
C5 Cr C3 C4 29.68(12) . . . . ?
C2 Cr C3 C4 131.74(18) . . . . ?
C6 Cr C3 C4 66.52(12) . . . . ?
C1 Cr C3 C4 102.39(13) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
Cr C3 C4 C5 -54.53(16) . . . . ?
C2 C3 C4 Cr 55.97(17) . . . . ?
C13 Cr C4 C5 -149.13(12) . . . . ?
C15 Cr C4 C5 94.7(2) . . . . ?
C14 Cr C4 C5 -61.16(13) . . . . ?
C3 Cr C4 C5 130.77(18) . . . . ?
C2 Cr C4 C5 101.70(13) . . . . ?
C6 Cr C4 C5 28.75(11) . . . . ?
C1 Cr C4 C5 65.13(12) . . . . ?
C13 Cr C4 C3 80.10(13) . . . . ?
C15 Cr C4 C3 -36.0(3) . . . . ?
C14 Cr C4 C3 168.07(13) . . . . ?
C5 Cr C4 C3 -130.77(18) . . . . ?
C2 Cr C4 C3 -29.07(12) . . . . ?
C6 Cr C4 C3 -102.02(13) . . . . ?
C1 Cr C4 C3 -65.64(12) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
Cr C4 C5 C6 -56.00(16) . . . . ?
C3 C4 C5 Cr 54.48(16) . . . . ?
C13 Cr C5 C4 40.16(16) . . . . ?
C15 Cr C5 C4 -145.76(14) . . . . ?
C14 Cr C5 C4 124.14(13) . . . . ?
C3 Cr C5 C4 -29.92(12) . . . . ?
C2 Cr C5 C4 -66.54(12) . . . . ?
C6 Cr C5 C4 -132.85(17) . . . . ?
C1 Cr C5 C4 -102.96(13) . . . . ?
C13 Cr C5 C6 173.01(11) . . . . ?
C15 Cr C5 C6 -12.91(18) . . . . ?
C14 Cr C5 C6 -103.01(12) . . . . ?
C3 Cr C5 C6 102.93(12) . . . . ?
C4 Cr C5 C6 132.85(17) . . . . ?
C2 Cr C5 C6 66.31(11) . . . . ?
C1 Cr C5 C6 29.89(10) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
Cr C5 C6 C1 -57.10(15) . . . . ?
C4 C5 C6 C7 -178.09(17) . . . . ?
Cr C5 C6 C7 126.31(16) . . . . ?
C4 C5 C6 Cr 55.60(16) . . . . ?
N C1 C6 C5 -175.34(17) . . . . ?
C2 C1 C6 C5 4.5(2) . . . . ?
Cr C1 C6 C5 55.13(15) . . . . ?
N C1 C6 C7 1.2(3) . . . . ?
C2 C1 C6 C7 -178.95(16) . . . . ?
Cr C1 C6 C7 -128.37(17) . . . . ?
N C1 C6 Cr 129.53(17) . . . . ?
C2 C1 C6 Cr -50.58(14) . . . . ?
C13 Cr C6 C5 -20.7(3) . . . . ?
C15 Cr C6 C5 171.49(12) . . . . ?
C14 Cr C6 C5 79.22(12) . . . . ?
C3 Cr C6 C5 -65.43(12) . . . . ?
C4 Cr C6 C5 -28.49(11) . . . . ?
C2 Cr C6 C5 -101.74(12) . . . . ?
C1 Cr C6 C5 -129.96(16) . . . . ?
C13 Cr C6 C1 109.3(3) . . . . ?
C15 Cr C6 C1 -58.55(12) . . . . ?
C14 Cr C6 C1 -150.82(12) . . . . ?
C5 Cr C6 C1 129.96(16) . . . . ?
C3 Cr C6 C1 64.53(11) . . . . ?
C4 Cr C6 C1 101.47(12) . . . . ?
C2 Cr C6 C1 28.22(11) . . . . ?
C13 Cr C6 C7 -132.5(3) . . . . ?
C15 Cr C6 C7 59.71(18) . . . . ?
C14 Cr C6 C7 -32.56(18) . . . . ?
C5 Cr C6 C7 -111.8(2) . . . . ?
C3 Cr C6 C7 -177.22(18) . . . . ?
C4 Cr C6 C7 -140.27(19) . . . . ?
C2 Cr C6 C7 146.48(19) . . . . ?
C1 Cr C6 C7 118.3(2) . . . . ?
C5 C6 C7 C12 -112.1(2) . . . . ?
C1 C6 C7 C12 71.4(2) . . . . ?
Cr C6 C7 C12 -24.3(3) . . . . ?
C5 C6 C7 C8 65.8(2) . . . . ?
C1 C6 C7 C8 -110.7(2) . . . . ?
Cr C6 C7 C8 153.52(15) . . . . ?
C12 C7 C8 C9 0.3(3) . . . . ?
C6 C7 C8 C9 -177.56(18) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
C6 C7 C12 C11 177.58(18) . . . . ?
C10 C11 C12 C7 0.1(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 26.39
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.746
_refine_diff_density_min -0.392
_refine_diff_density_rms 0.067
# File processed with modiCIFer (v.3-27-2007). I.A.Guzei, UW-Madi
#3. data
data_czerwinski07
_database_code_depnum_ccdc_archive 'CCDC 778548'
#TrackingRef '- czepaper_revised.cif'
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C15 H11 Cr N O3'
_chemical_formula_sum 'C15 H11 Cr N O3'
_chemical_formula_weight 305.25
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr 0.3209 0.6236 '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 1 21/n 1 '
_symmetry_space_group_name_Hall '-P 2yn '
_symmetry_int_tables_number 14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 6.3121(6)
_cell_length_b 12.3958(12)
_cell_length_c 16.2900(15)
_cell_angle_alpha 90.00
_cell_angle_beta 96.9940(10)
_cell_angle_gamma 90.00
_cell_volume 1265.1(2)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9917
_cell_measurement_theta_min 2.5194
_cell_measurement_theta_max 29.9685
_exptl_crystal_description block
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.41
_exptl_crystal_size_mid 0.39
_exptl_crystal_size_min 0.35
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.603
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 624
_exptl_absorpt_coefficient_mu 0.909
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS (Bruker-AXS, 2007)
;
_exptl_absorpt_correction_T_min 0.7068
_exptl_absorpt_correction_T_max 0.7414
_exptl_special_details ?
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD-1000 area detector'
_diffrn_measurement_method '0.30\% \w and 0.4 \% \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 17223
_diffrn_reflns_av_R_equivalents 0.0242
_diffrn_reflns_av_sigmaI/netI 0.0171
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_theta_min 2.52
_diffrn_reflns_theta_max 29.97
_reflns_number_total 3465
_reflns_number_gt 3173
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'SMART Ver. 5.622 (Bruker-AXS, 2000)'
_computing_cell_refinement 'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_reduction 'SAINT Ver. 7.24A'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement SHELXTL
_computing_molecular_graphics SHELXTL
_computing_publication_material 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.
;
_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^)+(0.0527P)^2^+0.3715P] 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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3465
_refine_ls_number_parameters 187
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0305
_refine_ls_R_factor_gt 0.0275
_refine_ls_wR_factor_ref 0.0795
_refine_ls_wR_factor_gt 0.0770
_refine_ls_goodness_of_fit_ref 1.042
_refine_ls_restrained_S_all 1.042
_refine_ls_shift/su_max 0.002
_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
Cr1 Cr 0.42569(3) 0.544386(14) 0.234752(10) 0.01133(7) Uani 1 1 d . . .
O1 O 0.16441(17) 0.44348(9) 0.08897(6) 0.0287(2) Uani 1 1 d . . .
O2 O 0.72769(15) 0.61117(8) 0.11607(6) 0.0233(2) Uani 1 1 d . . .
O3 O 0.69948(15) 0.34701(7) 0.25637(6) 0.02193(19) Uani 1 1 d . . .
N1 N 0.16206(19) 0.14168(9) 0.54064(7) 0.0205(2) Uani 1 1 d . . .
H1A H 0.256(3) 0.0903(15) 0.5439(11) 0.025 Uiso 1 1 d . . .
H1B H 0.039(3) 0.1271(15) 0.5460(11) 0.025 Uiso 1 1 d . . .
C1 C 0.13487(18) 0.56250(10) 0.29877(7) 0.0146(2) Uani 1 1 d . . .
H1 H 0.0029 0.5251 0.2888 0.018 Uiso 1 1 calc R . .
C2 C 0.16502(19) 0.65878(9) 0.25417(7) 0.0165(2) Uani 1 1 d . . .
H2 H 0.0529 0.6854 0.2153 0.020 Uiso 1 1 calc R . .
C3 C 0.3592(2) 0.71445(10) 0.26734(7) 0.0172(2) Uani 1 1 d . . .
H3 H 0.3794 0.7787 0.2374 0.021 Uiso 1 1 calc R . .
C4 C 0.52539(19) 0.67414(9) 0.32569(7) 0.0161(2) Uani 1 1 d . . .
H4 H 0.6573 0.7117 0.3352 0.019 Uiso 1 1 calc R . .
C5 C 0.49568(18) 0.57913(9) 0.36932(7) 0.0143(2) Uani 1 1 d . . .
H5 H 0.6093 0.5524 0.4075 0.017 Uiso 1 1 calc R . .
C6 C 0.29797(18) 0.52151(9) 0.35764(7) 0.0127(2) Uani 1 1 d . . .
C7 C 0.26512(18) 0.42227(9) 0.40505(6) 0.0130(2) Uani 1 1 d . . .
C8 C 0.42754(18) 0.34605(9) 0.42428(7) 0.0143(2) Uani 1 1 d . . .
H8 H 0.5642 0.3587 0.4074 0.017 Uiso 1 1 calc R . .
C9 C 0.39294(18) 0.25259(9) 0.46748(7) 0.0154(2) Uani 1 1 d . . .
H9 H 0.5049 0.2015 0.4787 0.018 Uiso 1 1 calc R . .
C10 C 0.19432(19) 0.23277(9) 0.49472(7) 0.0153(2) Uani 1 1 d . . .
C11 C 0.03265(19) 0.30985(10) 0.47759(7) 0.0167(2) Uani 1 1 d . . .
H11 H -0.1017 0.2990 0.4970 0.020 Uiso 1 1 calc R . .
C12 C 0.06715(18) 0.40196(9) 0.43254(7) 0.0155(2) Uani 1 1 d . . .
H12 H -0.0458 0.4522 0.4201 0.019 Uiso 1 1 calc R . .
C13 C 0.26300(19) 0.48217(10) 0.14584(7) 0.0180(2) Uani 1 1 d . . .
C14 C 0.61036(19) 0.58852(10) 0.16215(7) 0.0160(2) Uani 1 1 d . . .
C15 C 0.58934(19) 0.42170(10) 0.24764(7) 0.0154(2) Uani 1 1 d . . .
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
Cr1 0.01181(11) 0.01127(11) 0.01074(11) -0.00020(5) 0.00070(7) -0.00061(6)
O1 0.0264(5) 0.0355(6) 0.0228(5) -0.0108(4) -0.0023(4) -0.0058(4)
O2 0.0201(4) 0.0289(5) 0.0218(4) 0.0048(4) 0.0061(3) -0.0024(4)
O3 0.0248(5) 0.0188(4) 0.0229(4) 0.0010(3) 0.0058(3) 0.0058(3)
N1 0.0206(5) 0.0193(5) 0.0218(5) 0.0064(4) 0.0031(4) -0.0022(4)
C1 0.0132(5) 0.0155(5) 0.0153(5) 0.0001(4) 0.0019(4) 0.0014(4)
C2 0.0174(5) 0.0151(5) 0.0170(5) 0.0011(4) 0.0016(4) 0.0046(4)
C3 0.0229(6) 0.0120(5) 0.0170(5) 0.0003(4) 0.0030(4) 0.0008(4)
C4 0.0190(5) 0.0141(5) 0.0150(5) -0.0028(4) 0.0014(4) -0.0030(4)
C5 0.0151(5) 0.0148(5) 0.0125(5) -0.0018(4) 0.0006(4) -0.0003(4)
C6 0.0136(5) 0.0126(5) 0.0123(5) -0.0011(4) 0.0027(4) 0.0005(4)
C7 0.0144(5) 0.0136(5) 0.0108(4) -0.0005(4) 0.0005(4) 0.0002(4)
C8 0.0137(5) 0.0166(5) 0.0127(5) 0.0007(4) 0.0019(4) 0.0008(4)
C9 0.0161(5) 0.0161(5) 0.0137(5) 0.0005(4) 0.0011(4) 0.0029(4)
C10 0.0190(5) 0.0156(5) 0.0111(4) -0.0003(4) 0.0007(4) -0.0023(4)
C11 0.0142(5) 0.0187(6) 0.0172(5) 0.0007(4) 0.0029(4) -0.0019(4)
C12 0.0143(5) 0.0168(5) 0.0154(5) -0.0005(4) 0.0018(4) 0.0013(4)
C13 0.0170(5) 0.0199(6) 0.0175(5) -0.0016(4) 0.0037(4) -0.0011(4)
C14 0.0158(5) 0.0157(5) 0.0157(5) 0.0007(4) -0.0013(4) -0.0009(4)
C15 0.0179(5) 0.0162(5) 0.0126(4) -0.0008(4) 0.0037(4) -0.0018(4)
_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
Cr1 C15 1.8361(12) . yes
Cr1 C13 1.8398(12) . yes
Cr1 C14 1.8419(12) . yes
Cr1 C2 2.2237(12) . yes
Cr1 C4 2.2249(11) . yes
Cr1 C5 2.2249(11) . yes
Cr1 C3 2.2263(12) . yes
Cr1 C1 2.2302(12) . yes
Cr1 C6 2.2651(11) . yes
O1 C13 1.1555(16) . ?
O2 C14 1.1516(15) . ?
O3 C15 1.1561(15) . ?
N1 C10 1.3832(16) . ?
N1 H1A 0.868(19) . ?
N1 H1B 0.81(2) . ?
C1 C6 1.4133(15) . ?
C1 C2 1.4220(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.4000(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.4182(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.4000(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.4304(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4805(16) . ?
C7 C12 1.4006(16) . ?
C7 C8 1.4013(15) . ?
C8 C9 1.3865(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.4016(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.4010(17) . ?
C11 C12 1.3888(16) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
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
C15 Cr1 C13 89.72(5) . . yes
C15 Cr1 C14 85.89(5) . . yes
C13 Cr1 C14 87.43(5) . . yes
C15 Cr1 C2 158.07(5) . . yes
C13 Cr1 C2 91.58(5) . . yes
C14 Cr1 C2 116.04(5) . . yes
C15 Cr1 C4 114.40(5) . . yes
C13 Cr1 C4 155.88(5) . . yes
C14 Cr1 C4 93.61(5) . . yes
C2 Cr1 C4 66.33(4) . . yes
C15 Cr1 C5 90.35(5) . . yes
C13 Cr1 C5 151.84(5) . . yes
C14 Cr1 C5 120.66(5) . . yes
C2 Cr1 C5 78.35(4) . . yes
C4 Cr1 C5 36.67(4) . . yes
C15 Cr1 C3 151.27(5) . . yes
C13 Cr1 C3 118.76(5) . . yes
C14 Cr1 C3 91.40(5) . . yes
C2 Cr1 C3 36.67(5) . . yes
C4 Cr1 C3 37.16(4) . . yes
C5 Cr1 C3 66.57(4) . . yes
C15 Cr1 C1 120.90(5) . . yes
C13 Cr1 C1 89.89(5) . . yes
C14 Cr1 C1 153.08(5) . . yes
C2 Cr1 C1 37.24(4) . . yes
C4 Cr1 C1 78.35(4) . . yes
C5 Cr1 C1 66.16(4) . . yes
C3 Cr1 C1 66.63(4) . . yes
C15 Cr1 C6 92.93(5) . . yes
C13 Cr1 C6 114.75(5) . . yes
C14 Cr1 C6 157.80(5) . . yes
C2 Cr1 C6 66.73(4) . . yes
C4 Cr1 C6 66.69(4) . . yes
C5 Cr1 C6 37.14(4) . . yes
C3 Cr1 C6 79.05(4) . . yes
C1 Cr1 C6 36.64(4) . . yes
C10 N1 H1A 119.2(12) . . ?
C10 N1 H1B 116.4(13) . . ?
H1A N1 H1B 119.1(18) . . ?
C6 C1 C2 121.11(11) . . ?
C6 C1 Cr1 73.03(7) . . ?
C2 C1 Cr1 71.13(7) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
Cr1 C1 H1 128.7 . . ?
C3 C2 C1 120.30(10) . . ?
C3 C2 Cr1 71.76(7) . . ?
C1 C2 Cr1 71.63(6) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
Cr1 C2 H2 129.1 . . ?
C2 C3 C4 119.43(11) . . ?
C2 C3 Cr1 71.56(7) . . ?
C4 C3 Cr1 71.37(7) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
Cr1 C3 H3 129.1 . . ?
C5 C4 C3 120.19(11) . . ?
C5 C4 Cr1 71.66(6) . . ?
C3 C4 Cr1 71.47(7) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
Cr1 C4 H4 129.4 . . ?
C4 C5 C6 121.41(10) . . ?
C4 C5 Cr1 71.66(6) . . ?
C6 C5 Cr1 72.96(6) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
Cr1 C5 H5 128.4 . . ?
C1 C6 C5 117.54(10) . . ?
C1 C6 C7 121.07(10) . . ?
C5 C6 C7 121.39(10) . . ?
C1 C6 Cr1 70.34(6) . . ?
C5 C6 Cr1 69.91(6) . . ?
C7 C6 Cr1 130.74(8) . . ?
C12 C7 C8 117.66(10) . . ?
C12 C7 C6 120.21(10) . . ?
C8 C7 C6 122.12(10) . . ?
C9 C8 C7 121.37(10) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 120.63(11) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N1 C10 C11 120.85(11) . . ?
N1 C10 C9 120.71(11) . . ?
C11 C10 C9 118.38(11) . . ?
C12 C11 C10 120.58(11) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 121.34(11) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
O1 C13 Cr1 178.51(11) . . ?
O2 C14 Cr1 176.83(11) . . ?
O3 C15 Cr1 177.29(11) . . ?
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
C15 Cr1 C1 C6 45.16(8) . . . . ?
C13 Cr1 C1 C6 134.77(8) . . . . ?
C14 Cr1 C1 C6 -141.14(10) . . . . ?
C2 Cr1 C1 C6 -132.47(10) . . . . ?
C4 Cr1 C1 C6 -66.44(7) . . . . ?
C5 Cr1 C1 C6 -29.97(7) . . . . ?
C3 Cr1 C1 C6 -103.56(7) . . . . ?
C15 Cr1 C1 C2 177.63(7) . . . . ?
C13 Cr1 C1 C2 -92.76(7) . . . . ?
C14 Cr1 C1 C2 -8.67(14) . . . . ?
C4 Cr1 C1 C2 66.03(7) . . . . ?
C5 Cr1 C1 C2 102.50(7) . . . . ?
C3 Cr1 C1 C2 28.91(7) . . . . ?
C6 Cr1 C1 C2 132.47(10) . . . . ?
C6 C1 C2 C3 0.66(17) . . . . ?
Cr1 C1 C2 C3 -54.83(10) . . . . ?
C6 C1 C2 Cr1 55.49(10) . . . . ?
C15 Cr1 C2 C3 126.55(13) . . . . ?
C13 Cr1 C2 C3 -140.26(7) . . . . ?
C14 Cr1 C2 C3 -52.35(8) . . . . ?
C4 Cr1 C2 C3 29.74(7) . . . . ?
C5 Cr1 C2 C3 66.25(7) . . . . ?
C1 Cr1 C2 C3 132.00(10) . . . . ?
C6 Cr1 C2 C3 103.37(7) . . . . ?
C15 Cr1 C2 C1 -5.45(16) . . . . ?
C13 Cr1 C2 C1 87.73(7) . . . . ?
C14 Cr1 C2 C1 175.64(7) . . . . ?
C4 Cr1 C2 C1 -102.27(7) . . . . ?
C5 Cr1 C2 C1 -65.75(7) . . . . ?
C3 Cr1 C2 C1 -132.00(10) . . . . ?
C6 Cr1 C2 C1 -28.63(6) . . . . ?
C1 C2 C3 C4 -0.15(17) . . . . ?
Cr1 C2 C3 C4 -54.92(10) . . . . ?
C1 C2 C3 Cr1 54.77(10) . . . . ?
C15 Cr1 C3 C2 -141.38(10) . . . . ?
C13 Cr1 C3 C2 46.80(8) . . . . ?
C14 Cr1 C3 C2 134.63(7) . . . . ?
C4 Cr1 C3 C2 -131.22(10) . . . . ?
C5 Cr1 C3 C2 -102.32(7) . . . . ?
C1 Cr1 C3 C2 -29.33(7) . . . . ?
C6 Cr1 C3 C2 -65.55(7) . . . . ?
C15 Cr1 C3 C4 -10.16(13) . . . . ?
C13 Cr1 C3 C4 178.02(7) . . . . ?
C14 Cr1 C3 C4 -94.14(8) . . . . ?
C2 Cr1 C3 C4 131.22(10) . . . . ?
C5 Cr1 C3 C4 28.91(7) . . . . ?
C1 Cr1 C3 C4 101.89(8) . . . . ?
C6 Cr1 C3 C4 65.67(7) . . . . ?
C2 C3 C4 C5 0.38(17) . . . . ?
Cr1 C3 C4 C5 -54.63(10) . . . . ?
C2 C3 C4 Cr1 55.01(10) . . . . ?
C15 Cr1 C4 C5 -53.30(8) . . . . ?
C13 Cr1 C4 C5 127.80(12) . . . . ?
C14 Cr1 C4 C5 -140.41(7) . . . . ?
C2 Cr1 C4 C5 102.67(8) . . . . ?
C3 Cr1 C4 C5 132.05(10) . . . . ?
C1 Cr1 C4 C5 65.54(7) . . . . ?
C6 Cr1 C4 C5 28.98(7) . . . . ?
C15 Cr1 C4 C3 174.66(7) . . . . ?
C13 Cr1 C4 C3 -4.25(15) . . . . ?
C14 Cr1 C4 C3 87.54(8) . . . . ?
C2 Cr1 C4 C3 -29.37(7) . . . . ?
C5 Cr1 C4 C3 -132.05(10) . . . . ?
C1 Cr1 C4 C3 -66.51(7) . . . . ?
C6 Cr1 C4 C3 -103.07(8) . . . . ?
C3 C4 C5 C6 -1.11(17) . . . . ?
Cr1 C4 C5 C6 -55.65(10) . . . . ?
C3 C4 C5 Cr1 54.55(10) . . . . ?
C15 Cr1 C5 C4 133.10(7) . . . . ?
C13 Cr1 C5 C4 -136.83(11) . . . . ?
C14 Cr1 C5 C4 47.67(9) . . . . ?
C2 Cr1 C5 C4 -65.83(7) . . . . ?
C3 Cr1 C5 C4 -29.26(7) . . . . ?
C1 Cr1 C5 C4 -102.93(8) . . . . ?
C6 Cr1 C5 C4 -132.52(10) . . . . ?
C15 Cr1 C5 C6 -94.38(7) . . . . ?
C13 Cr1 C5 C6 -4.31(14) . . . . ?
C14 Cr1 C5 C6 -179.81(7) . . . . ?
C2 Cr1 C5 C6 66.69(7) . . . . ?
C4 Cr1 C5 C6 132.52(10) . . . . ?
C3 Cr1 C5 C6 103.26(7) . . . . ?
C1 Cr1 C5 C6 29.59(6) . . . . ?
C2 C1 C6 C5 -1.33(16) . . . . ?
Cr1 C1 C6 C5 53.28(9) . . . . ?
C2 C1 C6 C7 178.96(10) . . . . ?
Cr1 C1 C6 C7 -126.43(10) . . . . ?
C2 C1 C6 Cr1 -54.61(10) . . . . ?
C4 C5 C6 C1 1.56(16) . . . . ?
Cr1 C5 C6 C1 -53.49(9) . . . . ?
C4 C5 C6 C7 -178.72(10) . . . . ?
Cr1 C5 C6 C7 126.22(10) . . . . ?
C4 C5 C6 Cr1 55.06(10) . . . . ?
C15 Cr1 C6 C1 -142.47(7) . . . . ?
C13 Cr1 C6 C1 -51.42(8) . . . . ?
C14 Cr1 C6 C1 131.26(12) . . . . ?
C2 Cr1 C6 C1 29.07(7) . . . . ?
C4 Cr1 C6 C1 102.17(8) . . . . ?
C5 Cr1 C6 C1 130.82(10) . . . . ?
C3 Cr1 C6 C1 65.36(7) . . . . ?
C15 Cr1 C6 C5 86.72(7) . . . . ?
C13 Cr1 C6 C5 177.76(7) . . . . ?
C14 Cr1 C6 C5 0.44(15) . . . . ?
C2 Cr1 C6 C5 -101.75(7) . . . . ?
C4 Cr1 C6 C5 -28.64(7) . . . . ?
C3 Cr1 C6 C5 -65.46(7) . . . . ?
C1 Cr1 C6 C5 -130.82(10) . . . . ?
C15 Cr1 C6 C7 -27.92(11) . . . . ?
C13 Cr1 C6 C7 63.13(11) . . . . ?
C14 Cr1 C6 C7 -114.19(14) . . . . ?
C2 Cr1 C6 C7 143.62(11) . . . . ?
C4 Cr1 C6 C7 -143.28(11) . . . . ?
C5 Cr1 C6 C7 -114.64(13) . . . . ?
C3 Cr1 C6 C7 179.91(11) . . . . ?
C1 Cr1 C6 C7 114.55(13) . . . . ?
C1 C6 C7 C12 -38.08(16) . . . . ?
C5 C6 C7 C12 142.22(11) . . . . ?
Cr1 C6 C7 C12 -128.10(10) . . . . ?
C1 C6 C7 C8 142.09(11) . . . . ?
C5 C6 C7 C8 -37.61(16) . . . . ?
Cr1 C6 C7 C8 52.06(15) . . . . ?
C12 C7 C8 C9 1.33(16) . . . . ?
C6 C7 C8 C9 -178.84(10) . . . . ?
C7 C8 C9 C10 -1.30(17) . . . . ?
C8 C9 C10 N1 -177.42(10) . . . . ?
C8 C9 C10 C11 -0.33(17) . . . . ?
N1 C10 C11 C12 178.99(11) . . . . ?
C9 C10 C11 C12 1.91(17) . . . . ?
C10 C11 C12 C7 -1.90(17) . . . . ?
C8 C7 C12 C11 0.27(16) . . . . ?
C6 C7 C12 C11 -179.57(10) . . . . ?
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
N1 H1A O1 0.868(19) 2.626(19) 3.3437(16) 140.8(15) 4_666
_diffrn_measured_fraction_theta_max 0.945
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max 0.488
_refine_diff_density_min -0.237
_refine_diff_density_rms 0.071
# File processed with modiCIFer (v.3-27-2007). I.A.Guzei, UW-Madison.
#4. data
data_czerwinski08
_database_code_depnum_ccdc_archive 'CCDC 778549'
#TrackingRef '- czepaper_revised.cif'
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C15 H11 Cr N O3'
_chemical_formula_sum 'C15 H11 Cr N O3'
_chemical_formula_weight 305.25
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr -0.1635 2.4439 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1 '
_symmetry_space_group_name_Hall '-P 1 '
_symmetry_int_tables_number 2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.4228(3)
_cell_length_b 8.8378(3)
_cell_length_c 9.1761(4)
_cell_angle_alpha 96.810(3)
_cell_angle_beta 108.190(3)
_cell_angle_gamma 90.924(3)
_cell_volume 643.32(4)
_cell_formula_units_Z 2
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9962
_cell_measurement_theta_min 5.05
_cell_measurement_theta_max 71.55
_exptl_crystal_description block
_exptl_crystal_colour red
_exptl_crystal_size_max 0.44
_exptl_crystal_size_mid 0.29
_exptl_crystal_size_min 0.26
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.576
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 312
_exptl_absorpt_coefficient_mu 7.381
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS (Bruker-AXS, 2007)
;
_exptl_absorpt_correction_T_min 0.1412
_exptl_absorpt_correction_T_max 0.2489
_exptl_special_details ?
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 1.54178
_diffrn_radiation_type Cu-K\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART APEX2 area detector'
_diffrn_measurement_method '0.50\\% \\w and 0.5 \\% \\f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 12763
_diffrn_reflns_av_R_equivalents 0.0168
_diffrn_reflns_av_sigmaI/netI 0.0106
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_theta_min 5.05
_diffrn_reflns_theta_max 71.55
_reflns_number_total 2365
_reflns_number_gt 2350
_reflns_threshold_expression I>2\\s(I)
_computing_data_collection 'APEX2 Ver. 2.1-4 (Bruker-AXS, 2007)'
_computing_cell_refinement 'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_reduction 'SAINT Ver. 7.24A'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement SHELXTL
_computing_molecular_graphics SHELXTL
_computing_publication_material 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.
;
_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\^)+(0.0349P)\^2\^+0.3690P]
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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2365
_refine_ls_number_parameters 189
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0216
_refine_ls_R_factor_gt 0.0214
_refine_ls_wR_factor_ref 0.0587
_refine_ls_wR_factor_gt 0.0586
_refine_ls_goodness_of_fit_ref 1.013
_refine_ls_restrained_S_all 1.013
_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
Cr1 Cr 0.91027(3) 0.12758(2) 0.24231(2) 0.01201(8) Uani 1 1 d . . .
O1 O 1.06761(14) -0.17528(12) 0.25122(14) 0.0257(3) Uani 1 1 d . . .
O2 O 0.65835(13) 0.00428(12) -0.06039(12) 0.0217(2) Uani 1 1 d . . .
O3 O 0.65681(13) 0.02134(12) 0.37973(12) 0.0206(2) Uani 1 1 d . . .
N1 N 1.34158(16) 0.17352(15) 0.36530(16) 0.0186(3) Uani 1 1 d . . .
H1A H 1.367(3) 0.125(2) 0.288(3) 0.027(5) Uiso 1 1 d . . .
H1B H 1.374(2) 0.136(2) 0.448(2) 0.020(5) Uiso 1 1 d . . .
C1 C 0.95057(18) 0.33829(15) 0.14862(16) 0.0156(3) Uani 1 1 d . . .
H1 H 0.8969 0.3616 0.0469 0.019 Uiso 1 1 calc R . .
C2 C 1.10168(18) 0.26343(16) 0.17917(17) 0.0166(3) Uani 1 1 d . . .
H2 H 1.1462 0.2341 0.0975 0.020 Uiso 1 1 calc R . .
C3 C 1.18803(18) 0.23134(15) 0.33077(17) 0.0161(3) Uani 1 1 d . . .
C4 C 1.10706(18) 0.25927(16) 0.44460(16) 0.0159(3) Uani 1 1 d . . .
H4 H 1.1556 0.2280 0.5437 0.019 Uiso 1 1 calc R . .
C5 C 0.95553(18) 0.33284(15) 0.41235(16) 0.0149(3) Uani 1 1 d . . .
H5 H 0.9046 0.3517 0.4912 0.018 Uiso 1 1 calc R . .
C6 C 0.87647(18) 0.37971(15) 0.26563(16) 0.0153(3) Uani 1 1 d . . .
C7 C 0.72546(18) 0.47034(16) 0.23857(16) 0.0157(3) Uani 1 1 d . . .
C8 C 0.60600(19) 0.44710(16) 0.31117(16) 0.0177(3) Uani 1 1 d . . .
H8 H 0.6154 0.3659 0.3720 0.021 Uiso 1 1 calc R . .
C9 C 0.47331(19) 0.54176(17) 0.29521(17) 0.0196(3) Uani 1 1 d . . .
H9 H 0.3924 0.5249 0.3450 0.024 Uiso 1 1 calc R . .
C10 C 0.45820(19) 0.66103(17) 0.20680(18) 0.0199(3) Uani 1 1 d . . .
H10 H 0.3690 0.7274 0.1983 0.024 Uiso 1 1 calc R . .
C11 C 0.57424(19) 0.68270(17) 0.13088(17) 0.0196(3) Uani 1 1 d . . .
H11 H 0.5627 0.7624 0.0679 0.023 Uiso 1 1 calc R . .
C12 C 0.70713(19) 0.58831(16) 0.14672(16) 0.0172(3) Uani 1 1 d . . .
H12 H 0.7863 0.6040 0.0947 0.021 Uiso 1 1 calc R . .
C13 C 1.00682(18) -0.05928(17) 0.24830(17) 0.0174(3) Uani 1 1 d . . .
C14 C 0.75758(18) 0.06042(16) 0.32840(16) 0.0155(3) Uani 1 1 d . . .
C15 C 0.75794(18) 0.05374(16) 0.05509(17) 0.0160(3) Uani 1 1 d . . .
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
Cr1 0.01264(13) 0.01121(13) 0.01207(13) 0.00174(8) 0.00368(9) 0.00051(8)
O1 0.0234(6) 0.0171(5) 0.0371(7) 0.0041(4) 0.0098(5) 0.0058(4)
O2 0.0208(5) 0.0230(5) 0.0173(5) -0.0003(4) 0.0013(4) 0.0002(4)
O3 0.0180(5) 0.0224(5) 0.0247(6) 0.0074(4) 0.0099(4) 0.0015(4)
N1 0.0162(6) 0.0215(6) 0.0181(7) 0.0043(5) 0.0048(5) 0.0018(5)
C1 0.0178(7) 0.0136(6) 0.0151(7) 0.0040(5) 0.0039(5) -0.0019(5)
C2 0.0176(7) 0.0167(7) 0.0167(7) 0.0025(5) 0.0073(6) -0.0013(5)
C3 0.0153(7) 0.0120(6) 0.0197(7) 0.0013(5) 0.0041(6) -0.0026(5)
C4 0.0179(7) 0.0133(6) 0.0143(7) 0.0018(5) 0.0022(5) -0.0023(5)
C5 0.0175(7) 0.0112(6) 0.0153(7) -0.0009(5) 0.0054(5) -0.0021(5)
C6 0.0166(7) 0.0105(6) 0.0175(7) 0.0012(5) 0.0041(5) -0.0026(5)
C7 0.0168(7) 0.0121(6) 0.0149(7) -0.0014(5) 0.0018(5) -0.0013(5)
C8 0.0202(7) 0.0152(7) 0.0172(7) 0.0025(5) 0.0050(6) -0.0003(5)
C9 0.0177(7) 0.0210(7) 0.0196(7) -0.0003(6) 0.0060(6) -0.0003(6)
C10 0.0171(7) 0.0177(7) 0.0215(7) -0.0002(6) 0.0018(6) 0.0031(5)
C11 0.0223(8) 0.0148(7) 0.0189(7) 0.0036(5) 0.0020(6) 0.0006(5)
C12 0.0185(7) 0.0161(7) 0.0162(7) 0.0016(5) 0.0046(5) -0.0018(5)
C13 0.0142(7) 0.0191(7) 0.0183(7) 0.0016(5) 0.0047(5) -0.0020(5)
C14 0.0173(7) 0.0122(6) 0.0154(7) 0.0022(5) 0.0024(5) 0.0029(5)
C15 0.0177(7) 0.0140(7) 0.0189(7) 0.0042(5) 0.0086(6) 0.0036(5)
_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
Cr1 C14 1.8307(15) . yes
Cr1 C15 1.8314(15) . yes
Cr1 C13 1.8516(15) . yes
Cr1 C5 2.1922(13) . yes
Cr1 C1 2.2054(14) . yes
Cr1 C6 2.2444(14) . yes
Cr1 C4 2.2477(14) . yes
Cr1 C2 2.2499(14) . yes
Cr1 C3 2.3541(14) . yes
O1 C13 1.1527(19) . ?
O2 C15 1.1580(18) . ?
O3 C14 1.1577(19) . ?
N1 C3 1.356(2) . ?
N1 H1A 0.87(2) . ?
N1 H1B 0.83(2) . ?
C1 C2 1.409(2) . ?
C1 C6 1.417(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.419(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.416(2) . ?
C4 C5 1.406(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.417(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.485(2) . ?
C7 C8 1.394(2) . ?
C7 C12 1.398(2) . ?
C8 C9 1.388(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
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 Cr1 C15 86.22(6) . . yes
C14 Cr1 C13 91.16(6) . . yes
C15 Cr1 C13 89.32(6) . . yes
C14 Cr1 C5 87.44(6) . . yes
C15 Cr1 C5 138.18(6) . . yes
C13 Cr1 C5 132.12(6) . . yes
C14 Cr1 C1 134.76(6) . . yes
C15 Cr1 C1 89.74(6) . . yes
C13 Cr1 C1 133.87(6) . . yes
C5 Cr1 C1 66.57(5) . . yes
C14 Cr1 C6 100.97(6) . . yes
C15 Cr1 C6 104.22(6) . . yes
C13 Cr1 C6 162.27(6) . . yes
C5 Cr1 C6 37.24(5) . . yes
C1 Cr1 C6 37.13(5) . . yes
C14 Cr1 C4 103.46(6) . . yes
C15 Cr1 C4 167.59(6) . . yes
C13 Cr1 C4 98.11(6) . . yes
C5 Cr1 C4 36.89(5) . . yes
C1 Cr1 C4 77.95(5) . . yes
C6 Cr1 C4 66.66(5) . . yes
C14 Cr1 C2 165.46(6) . . yes
C15 Cr1 C2 103.80(6) . . yes
C13 Cr1 C2 99.37(6) . . yes
C5 Cr1 C2 78.06(5) . . yes
C1 Cr1 C2 36.85(5) . . yes
C6 Cr1 C2 66.62(5) . . yes
C4 Cr1 C2 65.30(5) . . yes
C14 Cr1 C3 136.97(6) . . yes
C15 Cr1 C3 136.39(6) . . yes
C13 Cr1 C3 84.87(6) . . yes
C5 Cr1 C3 65.16(5) . . yes
C1 Cr1 C3 65.11(5) . . yes
C6 Cr1 C3 77.44(5) . . yes
C4 Cr1 C3 35.76(5) . . yes
C2 Cr1 C3 35.81(5) . . yes
C3 N1 H1A 116.3(13) . . ?
C3 N1 H1B 116.3(13) . . ?
H1A N1 H1B 115.7(18) . . ?
C2 C1 C6 121.71(13) . . ?
C2 C1 Cr1 73.29(8) . . ?
C6 C1 Cr1 72.93(8) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
Cr1 C1 H1 126.6 . . ?
C1 C2 C3 120.65(13) . . ?
C1 C2 Cr1 69.86(8) . . ?
C3 C2 Cr1 76.10(8) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
Cr1 C2 H2 126.2 . . ?
N1 C3 C4 120.97(13) . . ?
N1 C3 C2 121.31(14) . . ?
C4 C3 C2 117.71(13) . . ?
N1 C3 Cr1 135.34(10) . . ?
C4 C3 Cr1 68.02(8) . . ?
C2 C3 Cr1 68.09(8) . . ?
C5 C4 C3 120.66(13) . . ?
C5 C4 Cr1 69.41(8) . . ?
C3 C4 Cr1 76.22(8) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
Cr1 C4 H4 126.6 . . ?
C4 C5 C6 121.92(13) . . ?
C4 C5 Cr1 73.70(8) . . ?
C6 C5 Cr1 73.38(8) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
Cr1 C5 H5 125.7 . . ?
C1 C6 C5 116.73(13) . . ?
C1 C6 C7 122.25(13) . . ?
C5 C6 C7 121.01(13) . . ?
C1 C6 Cr1 69.94(8) . . ?
C5 C6 Cr1 69.38(8) . . ?
C7 C6 Cr1 132.50(10) . . ?
C8 C7 C12 118.83(13) . . ?
C8 C7 C6 121.33(13) . . ?
C12 C7 C6 119.70(13) . . ?
C9 C8 C7 120.49(14) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.33(14) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 119.59(14) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 120.19(14) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 120.54(14) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
O1 C13 Cr1 179.44(14) . . ?
O3 C14 Cr1 177.48(12) . . ?
O2 C15 Cr1 177.45(13) . . ?
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
C14 Cr1 C1 C2 161.78(9) . . . . ?
C15 Cr1 C1 C2 -113.82(9) . . . . ?
C13 Cr1 C1 C2 -25.01(12) . . . . ?
C5 Cr1 C1 C2 101.67(9) . . . . ?
C6 Cr1 C1 C2 131.78(12) . . . . ?
C4 Cr1 C1 C2 64.69(8) . . . . ?
C3 Cr1 C1 C2 29.34(8) . . . . ?
C14 Cr1 C1 C6 30.00(12) . . . . ?
C15 Cr1 C1 C6 114.40(9) . . . . ?
C13 Cr1 C1 C6 -156.80(9) . . . . ?
C5 Cr1 C1 C6 -30.11(8) . . . . ?
C4 Cr1 C1 C6 -67.10(8) . . . . ?
C2 Cr1 C1 C6 -131.78(12) . . . . ?
C3 Cr1 C1 C6 -102.44(9) . . . . ?
C6 C1 C2 C3 -2.1(2) . . . . ?
Cr1 C1 C2 C3 -59.02(12) . . . . ?
C6 C1 C2 Cr1 56.92(12) . . . . ?
C14 Cr1 C2 C1 -62.1(2) . . . . ?
C15 Cr1 C2 C1 70.39(9) . . . . ?
C13 Cr1 C2 C1 162.00(9) . . . . ?
C5 Cr1 C2 C1 -66.70(8) . . . . ?
C6 Cr1 C2 C1 -29.37(8) . . . . ?
C4 Cr1 C2 C1 -103.32(9) . . . . ?
C3 Cr1 C2 C1 -130.56(13) . . . . ?
C14 Cr1 C2 C3 68.4(2) . . . . ?
C15 Cr1 C2 C3 -159.05(9) . . . . ?
C13 Cr1 C2 C3 -67.44(9) . . . . ?
C5 Cr1 C2 C3 63.85(8) . . . . ?
C1 Cr1 C2 C3 130.56(13) . . . . ?
C6 Cr1 C2 C3 101.19(9) . . . . ?
C4 Cr1 C2 C3 27.23(8) . . . . ?
C1 C2 C3 N1 -173.24(13) . . . . ?
Cr1 C2 C3 N1 130.74(13) . . . . ?
C1 C2 C3 C4 7.8(2) . . . . ?
Cr1 C2 C3 C4 -48.17(12) . . . . ?
C1 C2 C3 Cr1 56.01(12) . . . . ?
C14 Cr1 C3 N1 87.06(17) . . . . ?
C15 Cr1 C3 N1 -82.73(17) . . . . ?
C13 Cr1 C3 N1 0.87(16) . . . . ?
C5 Cr1 C3 N1 142.46(17) . . . . ?
C1 Cr1 C3 N1 -143.10(17) . . . . ?
C6 Cr1 C3 N1 179.74(16) . . . . ?
C4 Cr1 C3 N1 112.40(18) . . . . ?
C2 Cr1 C3 N1 -112.95(19) . . . . ?
C14 Cr1 C3 C4 -25.34(12) . . . . ?
C15 Cr1 C3 C4 164.87(9) . . . . ?
C13 Cr1 C3 C4 -111.53(9) . . . . ?
C5 Cr1 C3 C4 30.06(8) . . . . ?
C1 Cr1 C3 C4 104.50(9) . . . . ?
C6 Cr1 C3 C4 67.34(8) . . . . ?
C2 Cr1 C3 C4 134.65(13) . . . . ?
C14 Cr1 C3 C2 -159.99(9) . . . . ?
C15 Cr1 C3 C2 30.22(12) . . . . ?
C13 Cr1 C3 C2 113.82(9) . . . . ?
C5 Cr1 C3 C2 -104.59(9) . . . . ?
C1 Cr1 C3 C2 -30.15(8) . . . . ?
C6 Cr1 C3 C2 -67.30(9) . . . . ?
C4 Cr1 C3 C2 -134.65(13) . . . . ?
N1 C3 C4 C5 173.78(13) . . . . ?
C2 C3 C4 C5 -7.3(2) . . . . ?
Cr1 C3 C4 C5 -55.51(12) . . . . ?
N1 C3 C4 Cr1 -130.72(13) . . . . ?
C2 C3 C4 Cr1 48.20(12) . . . . ?
C14 Cr1 C4 C5 -66.70(9) . . . . ?
C15 Cr1 C4 C5 73.9(3) . . . . ?
C13 Cr1 C4 C5 -159.86(9) . . . . ?
C1 Cr1 C4 C5 66.87(8) . . . . ?
C6 Cr1 C4 C5 29.60(8) . . . . ?
C2 Cr1 C4 C5 103.50(9) . . . . ?
C3 Cr1 C4 C5 130.77(12) . . . . ?
C14 Cr1 C4 C3 162.52(8) . . . . ?
C15 Cr1 C4 C3 -56.9(3) . . . . ?
C13 Cr1 C4 C3 69.36(9) . . . . ?
C5 Cr1 C4 C3 -130.77(12) . . . . ?
C1 Cr1 C4 C3 -63.90(8) . . . . ?
C6 Cr1 C4 C3 -101.18(9) . . . . ?
C2 Cr1 C4 C3 -27.27(8) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
Cr1 C4 C5 C6 -57.78(12) . . . . ?
C3 C4 C5 Cr1 58.77(12) . . . . ?
C14 Cr1 C5 C4 116.60(9) . . . . ?
C15 Cr1 C5 C4 -161.97(9) . . . . ?
C13 Cr1 C5 C4 27.35(12) . . . . ?
C1 Cr1 C5 C4 -101.44(9) . . . . ?
C6 Cr1 C5 C4 -131.47(12) . . . . ?
C2 Cr1 C5 C4 -64.55(8) . . . . ?
C3 Cr1 C5 C4 -29.19(8) . . . . ?
C14 Cr1 C5 C6 -111.93(9) . . . . ?
C15 Cr1 C5 C6 -30.50(13) . . . . ?
C13 Cr1 C5 C6 158.82(9) . . . . ?
C1 Cr1 C5 C6 30.03(8) . . . . ?
C4 Cr1 C5 C6 131.47(12) . . . . ?
C2 Cr1 C5 C6 66.92(9) . . . . ?
C3 Cr1 C5 C6 102.28(9) . . . . ?
C2 C1 C6 C5 -4.2(2) . . . . ?
Cr1 C1 C6 C5 52.86(11) . . . . ?
C2 C1 C6 C7 174.58(13) . . . . ?
Cr1 C1 C6 C7 -128.32(13) . . . . ?
C2 C1 C6 Cr1 -57.09(12) . . . . ?
C4 C5 C6 C1 4.8(2) . . . . ?
Cr1 C5 C6 C1 -53.14(11) . . . . ?
C4 C5 C6 C7 -174.04(12) . . . . ?
Cr1 C5 C6 C7 128.03(12) . . . . ?
C4 C5 C6 Cr1 57.93(12) . . . . ?
C14 Cr1 C6 C1 -158.80(9) . . . . ?
C15 Cr1 C6 C1 -69.96(9) . . . . ?
C13 Cr1 C6 C1 68.8(2) . . . . ?
C5 Cr1 C6 C1 130.47(12) . . . . ?
C4 Cr1 C6 C1 101.14(9) . . . . ?
C2 Cr1 C6 C1 29.16(8) . . . . ?
C3 Cr1 C6 C1 65.17(8) . . . . ?
C14 Cr1 C6 C5 70.73(9) . . . . ?
C15 Cr1 C6 C5 159.57(9) . . . . ?
C13 Cr1 C6 C5 -61.6(2) . . . . ?
C1 Cr1 C6 C5 -130.47(12) . . . . ?
C4 Cr1 C6 C5 -29.33(8) . . . . ?
C2 Cr1 C6 C5 -101.32(9) . . . . ?
C3 Cr1 C6 C5 -65.30(8) . . . . ?
C14 Cr1 C6 C7 -42.96(14) . . . . ?
C15 Cr1 C6 C7 45.88(15) . . . . ?
C13 Cr1 C6 C7 -175.31(17) . . . . ?
C5 Cr1 C6 C7 -113.69(17) . . . . ?
C1 Cr1 C6 C7 115.84(17) . . . . ?
C4 Cr1 C6 C7 -143.02(15) . . . . ?
C2 Cr1 C6 C7 145.00(15) . . . . ?
C3 Cr1 C6 C7 -178.99(14) . . . . ?
C1 C6 C7 C8 146.36(14) . . . . ?
C5 C6 C7 C8 -34.9(2) . . . . ?
Cr1 C6 C7 C8 54.75(19) . . . . ?
C1 C6 C7 C12 -37.9(2) . . . . ?
C5 C6 C7 C12 140.84(14) . . . . ?
Cr1 C6 C7 C12 -129.53(13) . . . . ?
C12 C7 C8 C9 -1.4(2) . . . . ?
C6 C7 C8 C9 174.32(13) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 1.7(2) . . . . ?
C9 C10 C11 C12 -1.8(2) . . . . ?
C10 C11 C12 C7 0.2(2) . . . . ?
C8 C7 C12 C11 1.4(2) . . . . ?
C6 C7 C12 C11 -174.44(13) . . . . ?
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
N1 H1A O2 0.87(2) 2.21(2) 3.0424(18) 160.9(19) 2_755
N1 H1B O3 0.83(2) 2.30(2) 3.0620(17) 153.0(17) 2_756
_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_theta_full 71.55
_diffrn_measured_fraction_theta_full 0.942
_refine_diff_density_max 0.288
_refine_diff_density_min -0.238
_refine_diff_density_rms 0.046