#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/57/4115729.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_4115729
loop_
_publ_author_name
'David A. Shultz'
'Rosario M. Fico'
'Paul D. Boyle'
'Jeff W. Kampf'
_publ_section_title
;
 Observation of a Hysteretic Phase Transition in a Crystalline Dinitroxide
 Biradical That Leads to Magnetic Bistability
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10403
_journal_page_last               10404
_journal_paper_doi               10.1021/ja011341v
_journal_volume                  123
_journal_year                    2001
_chemical_formula_moiety         'C28 H36 N2 O2 '
_chemical_formula_sum            'C28 H36 N2 O2'
_chemical_formula_weight         432.60
_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                104.577(8)
_cell_angle_beta                 99.635(8)
_cell_angle_gamma                94.942(8)
_cell_formula_units_Z            2
_cell_length_a                   6.1933(4)
_cell_length_b                   11.4950(10)
_cell_length_c                   17.478(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    148
_cell_measurement_theta_max      18.00
_cell_measurement_theta_min      11.50
_cell_volume                     1176.5(2)
_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       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4097
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         0.00
_diffrn_standards_decay_%        3.2
_diffrn_standards_interval_time  80
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .08
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             468.25
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .04
_refine_diff_density_max         .26
_refine_diff_density_min         -.24
_refine_ls_extinction_coef       0.68(17)
_refine_ls_extinction_method     Larson
_refine_ls_goodness_of_fit_obs   1.45
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         2809
_refine_ls_R_factor_all          .052
_refine_ls_R_factor_obs          .051
_refine_ls_shift/esd_max         .001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     '1/(σ²(F)+ .0005F²) '
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .054
_refine_ls_wR_factor_obs         .053
_reflns_number_observed          2818
_reflns_number_total             4097
_reflns_observed_criterion       'Inet > 1.0\s(Inet)'
_cod_data_source_file            ja011341v_2.cif
_cod_data_source_block           x00019
_cod_original_cell_volume        1176.48(19)
_cod_original_formula_sum        'C28 H36 N2 O2 '
_cod_database_code               4115729
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
O .6881(3) .32090(20) .46149(12) .0312(13) Uani O
N .4785(4) .3019(2) .46044(13) .0204(14) Uani n
C1 -.0423(4) .3160(2) .10274(16) .0169(15) Uani C
C2 -.0246(4) .3863(2) .17754(16) .0166(14) Uani C
C3 .0921(4) .3563(2) .25043(16) .0157(14) Uani C
C4 .2961(4) .3107(2) .25072(16) .0168(14) Uani C
C5 .4154(5) .2908(2) .31866(16) .0182(15) Uani C
C6 .3367(4) .3150(2) .39078(16) .0165(14) Uani C
C7 .1324(4) .3593(2) .39274(17) .0179(15) Uani C
C8 .0161(4) .3797(2) .32292(17) .0187(16) Uani C
C9 .0120(5) .1884(2) .07062(16) .0177(14) Uani C
C10 -.2017(5) .1303(3) .00888(18) .0207(16) Uani C
C11 .1937(5) .2126(3) .02385(18) .0215(16) Uani C
C12 .4075(5) .2710(2) .53177(16) .0200(14) Uani C
C13 .3897(6) .3886(3) .59332(19) .0274(18) Uani C
C14 .5906(5) .2067(3) .5677(2) .0283(18) Uani C
C15 .1925(5) .1843(3) .5055(2) .0287(18) Uani C
O' -.5729(3) .83372(17) .23851(12) .0224(11) Uani O
N' -.3641(4) .84267(20) .23657(14) .0177(13) Uani n
C3' -.1100(4) .5067(2) .19241(15) .0160(14) Uani C
C4' -.3297(4) .5160(2) .16000(16) .0167(15) Uani C
C5' -.4095(4) .6272(2) .17463(16) .0163(15) Uani C
C6' -.2711(4) .7326(2) .22123(16) .0158(14) Uani C
C7' -.0534(5) .7238(2) .25483(17) .0173(14) Uani C
C8' .0225(4) .6122(2) .24045(16) .0174(15) Uani C
C9' -.0957(5) .3428(3) .02138(16) .0183(14) Uani C
C10' -.2656(5) .2344(2) -.02962(17) .0206(16) Uani C
C11' .1259(5) .3248(3) -.00610(19) .0223(17) Uani C
C12' -.2540(4) .9704(2) .24862(17) .0189(15) Uani C
C13' -.4005(5) 1.0256(3) .19101(20) .0231(17) Uani C
C14' -.2476(6) 1.0380(3) .33555(20) .0323(19) Uani C
C15' -.0243(6) .9750(3) .2284(3) .039(2) Uani C
H4 .361(4) .301(2) .2040(16) .010(6) Uiso H
H5 .562(5) .268(2) .3206(15) .016(7) Uiso H
H7 .070(4) .377(2) .4421(15) .003(6) Uiso H
H8 -.120(5) .413(2) .3252(16) .017(7) Uiso H
H9 .054(4) .147(2) .1120(15) .009(6) Uiso H
H10a -.179(4) .060(2) -.0286(15) .010(7) Uiso H
H10b -.312(4) .100(2) .0337(15) .010(7) Uiso H
H11a .345(6) .230(3) .0577(19) .037(9) Uiso H
H11b .187(4) .142(3) -.0199(18) .020(7) Uiso H
H13a .351(5) .371(3) .642(2) .034(9) Uiso H
H13b .534(5) .438(3) .6090(18) .030(9) Uiso H
H13c .283(6) .437(3) .571(2) .045(10) Uiso H
H14a .604(6) .132(3) .524(2) .050(11) Uiso H
H14b .733(5) .255(3) .5811(17) .026(8) Uiso H
H14c .544(5) .188(3) .616(2) .039(9) Uiso H
H15a .067(6) .229(3) .488(2) .060(12) Uiso H
H15b .203(5) .111(3) .4611(19) .033(9) Uiso H
H15c .158(5) .161(3) .5520(18) .023(8) Uiso H
H4' -.423(4) .440(2) .1254(16) .016(7) Uiso H
H5' -.558(5) .633(2) .1554(16) .017(7) Uiso H
H7' .035(4) .793(2) .2867(15) .010(7) Uiso H
H8' .176(5) .611(2) .2656(16) .020(7) Uiso H
H9' -.138(4) .419(2) .0215(15) .010(7) Uiso H
H10a' -.423(5) .251(2) -.0274(17) .022(7) Uiso H
H10b' -.252(4) .216(2) -.0856(15) .005(6) Uiso H
H11a' .115(4) .310(2) -.0639(18) .018(7) Uiso H
H11b' .234(5) .398(3) .0211(17) .024(8) Uiso H
H13a' -.330(5) 1.114(3) .2010(16) .022(7) Uiso H
H13b' -.415(5) .979(3) .1338(20) .033(9) Uiso H
H13c' -.543(6) 1.026(3) .2013(18) .030(9) Uiso H
H14a' -.405(6) 1.036(3) .346(2) .049(11) Uiso H
H14b' -.160(6) .997(3) .369(2) .044(10) Uiso H
H14c' -.177(5) 1.121(3) .3453(18) .036(9) Uiso H
H15a' .088(6) .958(3) .271(2) .053(11) Uiso H
H15b' -.032(6) .920(3) .178(2) .048(12) Uiso H
H15c' .027(5) 1.060(3) .2306(17) .028(8) 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
1 3 -2
1 4 -1
-1 -2 5
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O N C6 115.6(2)
O N C12 118.1(2)
C6 N C12 126.3(2)
C2 C1 C9 132.1(2)
C2 C1 C9' 131.4(2)
C9 C1 C9' 96.2(2)
C1 C2 C3 123.3(2)
C1 C2 C3' 120.9(2)
C3 C2 C3' 115.7(2)
C2 C3 C4 120.6(2)
C2 C3 C8 122.6(2)
C4 C3 C8 116.6(2)
C3 C4 C5 122.0(3)
C3 C4 H4 119.4(14)
C5 C4 H4 118.4(15)
C4 C5 C6 120.6(2)
C4 C5 H5 122.0(15)
C6 C5 H5 117.1(15)
N C6 C5 117.3(2)
N C6 C7 123.4(2)
C5 C6 C7 119.2(2)
C6 C7 C8 118.9(2)
C6 C7 H7 122.1(13)
C8 C7 H7 119.1(13)
C3 C8 C7 122.8(2)
C3 C8 H8 118.7(16)
C7 C8 H8 118.5(16)
C1 C9 C10 100.7(2)
C1 C9 C11 101.1(2)
C1 C9 H9 114.3(14)
C10 C9 C11 108.1(2)
C10 C9 H9 115.5(15)
C11 C9 H9 115.3(15)
C9 C10 C10' 103.4(2)
C9 C10 H10a 111.3(15)
C9 C10 H10b 111.6(15)
C10' C10 H10a 113.6(15)
C10' C10 H10b 114.5(15)
H10a C10 H10b 102(2)
C9 C11 C11' 102.9(2)
C9 C11 H11a 113.1(18)
C9 C11 H11b 107.8(17)
C11' C11 H11a 111.9(18)
C11' C11 H11b 112.5(16)
H11a C11 H11b 108(2)
N C12 C13 108.7(2)
N C12 C14 106.4(2)
N C12 C15 110.6(2)
C13 C12 C14 109.8(2)
C13 C12 C15 112.5(3)
C14 C12 C15 108.7(2)
C12 C13 H13a 110.4(18)
C12 C13 H13b 108.3(18)
C12 C13 H13c 112.7(19)
H13a C13 H13b 107(3)
H13a C13 H13c 110(3)
H13b C13 H13c 106(3)
C12 C14 H14a 107.4(19)
C12 C14 H14b 112.4(17)
C12 C14 H14c 106.2(18)
H14a C14 H14b 105(3)
H14a C14 H14c 113(3)
H14b C14 H14c 112(3)
C12 C15 H15a 109(2)
C12 C15 H15b 111.2(18)
C12 C15 H15c 108.5(17)
H15a C15 H15b 110(3)
H15a C15 H15c 105(3)
H15b C15 H15c 111(2)
O' N' C6' 116.4(2)
O' N' C12' 114.80(19)
C6' N' C12' 128.7(2)
C2 C3' C4' 121.0(2)
C2 C3' C8' 121.4(2)
C4' C3' C8' 117.6(2)
C3' C4' C5' 121.0(2)
C3' C4' H4' 117.1(15)
C5' C4' H4' 122.0(15)
C4' C5' C6' 120.3(2)
C4' C5' H5' 120.9(16)
C6' C5' H5' 118.7(16)
N' C6' C5' 117.7(2)
N' C6' C7' 123.1(2)
C5' C6' C7' 119.0(2)
C6' C7' C8' 119.8(3)
C6' C7' H7' 118.5(15)
C8' C7' H7' 121.7(15)
C3' C8' C7' 122.1(2)
C3' C8' H8' 121.0(16)
C7' C8' H8' 116.8(16)
C1 C9' C10' 103.6(2)
C1 C9' C11' 99.5(2)
C1 C9' H9' 116.7(15)
C10' C9' C11' 107.4(2)
C10' C9' H9' 115.0(15)
C11' C9' H9' 113.2(15)
C10 C10' C9' 102.7(2)
C10 C10' H10a' 112.7(16)
C10 C10' H10b' 111.6(14)
C9' C10' H10a' 112.0(16)
C9' C10' H10b' 110.5(14)
H10a' C10' H10b' 107(2)
C11 C11' C9' 102.8(2)
C11 C11' H11a' 112.2(16)
C11 C11' H11b' 110.9(16)
C9' C11' H11a' 113.4(16)
C9' C11' H11b' 109.3(16)
H11a' C11' H11b' 108(2)
N' C12' C13' 106.6(2)
N' C12' C14' 106.7(2)
N' C12' C15' 113.2(2)
C13' C12' C14' 110.7(2)
C13' C12' C15' 108.0(3)
C14' C12' C15' 111.5(3)
C12' C13' H13a' 106.8(15)
C12' C13' H13b' 111.9(17)
C12' C13' H13c' 111.5(18)
H13a' C13' H13b' 111(2)
H13a' C13' H13c' 108(2)
H13b' C13' H13c' 106(3)
C12' C14' H14a' 109.3(19)
C12' C14' H14b' 107.6(19)
C12' C14' H14c' 108.7(18)
H14a' C14' H14b' 109(3)
H14a' C14' H14c' 111(3)
H14b' C14' H14c' 109(3)
C12' C15' H15a' 112(2)
C12' C15' H15b' 108(2)
C12' C15' H15c' 107.8(17)
H15a' C15' H15b' 111(3)
H15a' C15' H15c' 102(3)
H15b' C15' H15c' 113(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O N 1.294(3)
N C6 1.426(3)
N C12 1.501(4)
C1 C2 1.334(4)
C1 C9 1.521(4)
C1 C9' 1.519(4)
C2 C3 1.490(4)
C2 C3' 1.501(4)
C3 C4 1.408(4)
C3 C8 1.396(4)
C4 C5 1.371(4)
C4 H4 .96(3)
C5 C6 1.399(4)
C5 H5 .96(3)
C6 C7 1.406(4)
C7 C8 1.393(4)
C7 H7 .98(3)
C8 H8 .96(3)
C9 C10 1.539(4)
C9 C11 1.543(4)
C9 H9 .97(3)
C10 C10' 1.561(4)
C10 H10a .94(3)
C10 H10b .95(3)
C11 C11' 1.572(4)
C11 H11a 1.00(3)
C11 H11b .96(3)
C12 C13 1.526(4)
C12 C14 1.538(4)
C12 C15 1.521(4)
C13 H13a .97(4)
C13 H13b .97(3)
C13 H13c .99(4)
C14 H14a 1.01(4)
C14 H14b .96(3)
C14 H14c 1.00(4)
C15 H15a 1.02(4)
C15 H15b 1.01(3)
C15 H15c .97(3)
O' N' 1.295(3)
N' C6' 1.418(3)
N' C12' 1.514(3)
C3' C4' 1.407(4)
C3' C8' 1.391(4)
C4' C5' 1.389(4)
C4' H4' .99(3)
C5' C6' 1.399(4)
C5' H5' .94(3)
C6' C7' 1.400(4)
C7' C8' 1.382(4)
C7' H7' .92(3)
C8' H8' .98(3)
C9' C10' 1.535(4)
C9' C11' 1.542(4)
C9' H9' .93(3)
C10' H10a' 1.02(3)
C10' H10b' .97(3)
C11' H11a' .97(3)
C11' H11b' .99(3)
C12' C13' 1.534(4)
C12' C14' 1.515(4)
C12' C15' 1.521(4)
C13' H13a' 1.03(3)
C13' H13b' .99(3)
C13' H13c' .93(3)
C14' H14a' 1.02(4)
C14' H14b' .97(4)
C14' H14c' .97(4)
C15' H15a' .99(4)
C15' H15b' .94(4)
C15' H15c' .99(3)
