#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/34/4113443.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4113443
loop_
_publ_author_name
'David A. Shultz'
'Kira E. Vostrikova'
'Scot H. Bodnar'
'Hyun-Joo Koo'
'Myung-Hwan Whangbo'
'Martin L. Kirk'
'Ezra C. Depperman'
'Jeff W. Kampf'
_publ_section_title
;
 Trends in Metal-Biradical Exchange Interaction for First-Row MII(Nitronyl
 Nitroxide-Semiquinone) Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1607
_journal_page_last               1617
_journal_paper_doi               10.1021/ja020715x
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C17 H25 N2 O4 '
_chemical_formula_sum            'C17 H25 N2 O4'
_chemical_formula_weight         321.39
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                86.415(9)
_cell_angle_beta                 78.737(9)
_cell_angle_gamma                76.502(7)
_cell_formula_units_Z            2
_cell_length_a                   6.8165(6)
_cell_length_b                   10.0414(9)
_cell_length_c                   12.7020(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    148
_cell_measurement_theta_max      18.00
_cell_measurement_theta_min      16.00
_cell_volume                     828.99(14)
_computing_cell_refinement       'CAD4 Argus'
_computing_data_collection       'CAD4 Argus'
_computing_data_reduction        'NRCVAX DATRD2'
_computing_molecular_graphics    NRCVAX
_computing_publication_material  'NRCVAX TABLES Jan 94 Version'
_computing_structure_refinement  'NRCVAX LSTSQ'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      148
_diffrn_measurement_device       'Nonius CAD-4    '
_diffrn_measurement_method       'Omega scan b/P/b        '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'xray tube'
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3592
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.20
_diffrn_standards_decay_%        1.3
_diffrn_standards_interval_time  80
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .09
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       plates
_exptl_crystal_F_000             346.22
_exptl_crystal_size_max          .48
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .06
_refine_diff_density_max         .33
_refine_diff_density_min         -.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.94
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         2936
_refine_ls_R_factor_all          .037
_refine_ls_R_factor_obs          .037
_refine_ls_shift/esd_max         .000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     '1/(σ²(F)+ .0002F²) '
_refine_ls_wR_factor_all         .044
_refine_ls_wR_factor_obs         .044
_reflns_number_observed          2939
_reflns_number_total             3592
_reflns_observed_criterion       'Inet > 1.0\s(Inet)'
_cod_data_source_file            ja020715x_2.cif
_cod_data_source_block           x00050
_cod_original_cell_volume        828.99(13)
_cod_original_formula_sum        'C17 H25 N2 O4 '
_cod_database_code               4113443
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_type_symbol
O1 .24812(15) .05571(10) .41866(8) .0187(5) Uani O
O2 -.22370(15) .45252(10) .54406(8) .0205(5) Uani O
O3 .50498(15) .05625(11) .75534(8) .0186(5) Uani O
O4 .22064(16) .14351(10) .92101(7) .0168(5) Uani O
N1 .10840(16) .16937(11) .42249(8) .0128(5) Uani n
N2 -.12170(17) .35245(11) .48418(9) .0138(5) Uani n
C1 .02714(20) .24561(13) .51008(10) .0127(6) Uani C
C2 .02999(20) .23505(14) .32406(10) .0130(6) Uani C
C3 -.17526(20) .32981(13) .37837(10) .0135(6) Uani C
C4 .07997(20) .21763(13) .61643(10) .0126(6) Uani C
C5 .2783(2) .14736(13) .62888(11) .0135(6) Uani C
C6 .31965(20) .12443(13) .73154(10) .0132(6) Uani C
C7 .1674(2) .16987(13) .82176(10) .0127(6) Uani C
C8 -.03299(20) .23736(13) .81123(10) .0126(6) Uani C
C9 -.0711(2) .26038(13) .70697(11) .0131(6) Uani C
C21 .0057(2) .12648(15) .25236(11) .0177(7) Uani C
C22 .1879(2) .31369(16) .26513(12) .0181(7) Uani C
C31 -.3530(2) .25628(16) .40554(12) .0196(7) Uani C
C32 -.2387(2) .46564(15) .32075(12) .0189(7) Uani C
C81 -.2024(2) .28161(13) .91013(10) .0139(6) Uani C
C82 -.1361(2) .37626(15) .98010(12) .0197(7) Uani C
C83 -.4045(2) .35884(15) .87748(11) .0174(7) Uani C
C84 -.2442(2) .15402(15) .97616(11) .0183(7) Uani C
H3 .587(3) .017(2) .6990(17) .039(6) Uiso H
H4 .347(3) .0984(20) .9063(15) .032(5) Uiso H
H5 .382(2) .1145(15) .5666(13) .015(4) Uiso H
H9 -.203(2) .3066(16) .6951(12) .013(4) Uiso H
H21a -.066(3) .0582(17) .2923(14) .023(4) Uiso H
H21b -.073(3) .1744(19) .1982(15) .032(5) Uiso H
H21c .142(3) .0741(18) .2159(14) .027(5) Uiso H
H22a .323(3) .2463(17) .2439(13) .020(4) Uiso H
H22b .198(3) .3850(18) .3110(14) .026(4) Uiso H
H22c .146(3) .3534(17) .1986(14) .020(4) Uiso H
H31a -.307(3) .1690(19) .4430(14) .030(5) Uiso H
H31b -.470(3) .3200(18) .4518(15) .030(5) Uiso H
H31c -.399(3) .2371(19) .3408(15) .030(5) Uiso H
H32a -.245(3) .4451(18) .2476(15) .027(5) Uiso H
H32b -.369(3) .5170(18) .3603(14) .025(4) Uiso H
H32c -.132(3) .5201(18) .3144(14) .028(5) Uiso H
H82a -.243(3) .4033(17) 1.0448(14) .024(4) Uiso H
H82b -.119(3) .4658(18) .9390(14) .027(5) Uiso H
H82c -.009(3) .3332(18) 1.0045(14) .028(5) Uiso H
H83a -.459(3) .3029(17) .8322(14) .025(4) Uiso H
H83b -.509(3) .3829(17) .9409(14) .025(4) Uiso H
H83c -.390(2) .4456(17) .8390(13) .019(4) Uiso H
H84a -.284(3) .0889(17) .9307(14) .023(4) Uiso H
H84b -.117(3) .1029(18) 1.0042(14) .026(4) Uiso H
H84c -.358(3) .1811(17) 1.0397(14) .024(4) Uiso H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .003 .002 'International Tables Vol. IV Table 2.2B'
H .000 .000 'International Tables Vol. IV Table 2.2B'
N .006 .003 'International Tables Vol. IV Table 2.2B'
O .011 .006 'International Tables Vol. IV Table 2.2B'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 -2 -6
-1 1 -6
-2 -2 -6
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 O3 H3 111.3(13)
C7 O4 H4 103.2(12)
O1 N1 C1 125.25(11)
O1 N1 C2 122.41(10)
C1 N1 C2 112.23(10)
O2 N2 C1 126.76(11)
O2 N2 C3 121.80(10)
C1 N2 C3 110.98(10)
N1 C1 N2 108.17(11)
N1 C1 C4 126.59(12)
N2 C1 C4 125.19(11)
N1 C2 C3 99.87(10)
N1 C2 C21 110.45(11)
N1 C2 C22 106.87(10)
C3 C2 C21 114.72(11)
C3 C2 C22 113.48(11)
C21 C2 C22 110.66(11)
N2 C3 C2 100.13(10)
N2 C3 C31 105.70(11)
N2 C3 C32 110.51(11)
C2 C3 C31 113.02(11)
C2 C3 C32 115.40(11)
C31 C3 C32 111.11(12)
C1 C4 C5 121.01(12)
C1 C4 C9 119.03(12)
C5 C4 C9 119.96(12)
C4 C5 C6 118.42(12)
C4 C5 H5 120.2(9)
C6 C5 H5 121.3(9)
O3 C6 C5 124.56(12)
O3 C6 C7 114.40(11)
C5 C6 C7 121.03(12)
O4 C7 C6 117.53(11)
O4 C7 C8 121.01(12)
C6 C7 C8 121.45(11)
C7 C8 C9 116.58(12)
C7 C8 C81 121.52(11)
C9 C8 C81 121.89(12)
C4 C9 C8 122.52(12)
C4 C9 H9 117.3(9)
C8 C9 H9 120.2(9)
C2 C21 H21a 113.1(10)
C2 C21 H21b 107.3(10)
C2 C21 H21c 110.7(10)
H21a C21 H21b 109.5(15)
H21a C21 H21c 106.3(14)
H21b C21 H21c 109.8(14)
C2 C22 H22a 108.3(9)
C2 C22 H22b 109.8(10)
C2 C22 H22c 109.3(10)
H22a C22 H22b 112.0(14)
H22a C22 H22c 106.6(13)
H22b C22 H22c 110.7(14)
C3 C31 H31a 109.1(11)
C3 C31 H31b 106.9(10)
C3 C31 H31c 111.6(11)
H31a C31 H31b 112.0(14)
H31a C31 H31c 108.8(15)
H31b C31 H31c 108.5(15)
C3 C32 H32a 107.3(10)
C3 C32 H32b 109.3(10)
C3 C32 H32c 110.8(10)
H32a C32 H32b 113.4(14)
H32a C32 H32c 106.3(15)
H32b C32 H32c 109.8(14)
C8 C81 C82 110.22(11)
C8 C81 C83 111.52(11)
C8 C81 C84 109.54(11)
C82 C81 C83 108.16(11)
C82 C81 C84 109.68(11)
C83 C81 C84 107.67(11)
C81 C82 H82a 110.6(10)
C81 C82 H82b 110.7(10)
C81 C82 H82c 112.6(11)
H82a C82 H82b 106.3(13)
H82a C82 H82c 107.4(14)
H82b C82 H82c 108.9(14)
C81 C83 H83a 112.9(9)
C81 C83 H83b 109.8(10)
C81 C83 H83c 111.4(9)
H83a C83 H83b 106.6(14)
H83a C83 H83c 109.1(13)
H83b C83 H83c 106.7(14)
C81 C84 H84a 110.8(9)
C81 C84 H84b 110.7(10)
C81 C84 H84c 110.5(10)
H84a C84 H84b 108.0(13)
H84a C84 H84c 108.9(14)
H84b C84 H84c 107.8(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.3013(14)
O2 N2 1.2784(14)
O3 C6 1.3695(16)
O3 H3 .87(2)
O4 C7 1.3724(15)
O4 H4 .86(2)
N1 C1 1.3411(17)
N1 C2 1.5090(16)
N2 C1 1.3663(17)
N2 C3 1.5033(17)
C1 C4 1.4590(18)
C2 C3 1.5564(18)
C2 C21 1.5207(19)
C2 C22 1.5330(20)
C3 C31 1.5344(20)
C3 C32 1.5187(19)
C4 C5 1.4052(18)
C4 C9 1.4000(18)
C5 C6 1.3815(19)
C5 H5 .969(16)
C6 C7 1.4067(18)
C7 C8 1.4036(18)
C8 C9 1.3938(18)
C8 C81 1.5402(18)
C9 H9 .945(16)
C21 H21a .990(18)
C21 H21b .989(20)
C21 H21c .994(19)
C22 H22a 1.007(17)
C22 H22b .975(19)
C22 H22c .976(17)
C31 H31a .985(19)
C31 H31b 1.009(19)
C31 H31c .980(19)
C32 H32a .975(19)
C32 H32b .973(18)
C32 H32c .996(20)
C81 C82 1.5363(20)
C81 C83 1.5348(19)
C81 C84 1.5391(19)
C82 H82a .992(18)
C82 H82b 1.030(18)
C82 H82c .975(19)
C83 H83a 1.002(18)
C83 H83b .968(19)
C83 H83c .989(17)
C84 H84a 1.014(18)
C84 H84b 1.013(18)
C84 H84c 1.005(18)
