#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/14/2001465.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2001465
loop_
_publ_author_name
'Priya, V.'
'Shamala, N.'
'Viswamitra, M. A.'
'Ravindran, T.'
'Jeyaraman, R.'
_publ_section_title
;
 Structure of N-nitroso-2,4-diphenyl-3-azabicyclo[3.3.1]nonane
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1519
_journal_page_last               1522
_journal_paper_doi               10.1107/S0108270193001258
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C20 H22 N2 O'
_chemical_formula_weight         306.36
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.0
_cell_angle_beta                 91.80(10)
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   18.456(2)
_cell_length_b                   24.097(3)
_cell_length_c                   7.5400(10)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    295
_cell_measurement_theta_max      22
_cell_measurement_theta_min      9
_cell_volume                     3351.6(7)
_computing_data_collection       'SDP (Enraf-Nonius, 1985)'
_computing_structure_refinement
'SHELX400 (enhanced version of SHELX76; Sheldrick, 1976)'
_computing_structure_solution
'MULTAN87 (Debaerdemaeker, Germain, Main, Tate & Woolfson, 1987)'
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4318
_diffrn_reflns_theta_max         60
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.51
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.20
_exptl_crystal_description       Parallelepiped
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.362
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     296
_refine_ls_number_reflns         1925
_refine_ls_R_factor_obs          0.045
_refine_ls_shift/esd_max         0.006
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/σ²(|F|)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.045
_reflns_number_observed          1925
_reflns_number_total             2913
_reflns_observed_criterion       I>2.5\s(I)
_cod_data_source_file            li1040.cif
_cod_data_source_block           li1040_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/\s^2^(|F|)' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/\s^2^(|F|)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3351.5
_cod_database_code               2001465
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
C(1)A .9683(4) .1153(3) .8692(8) .073(3)
C(2)A .9470(3) .0978(2) .6771(6) .054(2)
N(3)A 1.0126(2) .09010(10) .5678(5) .051(2)
C(4)A 1.0873(3) .0817(2) .6352(7) .052(2)
C(5)A 1.0984(3) .1035(3) .8250(7) .060(2)
C(6)A 1.1101(4) .1664(3) .8429(9) .072(3)
C(7)A 1.0413(4) .1998(3) .7964(10) .077(3)
C(8)A .9786(4) .1777(3) .8949(10) .086(3)
C(9)A 1.0353(3) .0835(3) .9328(8) .073(3)
C(10)A .8912(3) .1370(2) .5904(8) .055(2)
C(11)A .9034(4) .1701(2) .4452(8) .063(2)
C(12)A .8496(5) .2064(2) .3825(10) .078(3)
C(13)A .7851(5) .2105(3) .4624(12) .086(4)
C(14)A .7727(4) .1779(3) .6056(12) .083(4)
C(15)A .8246(4) .1408(3) .6673(10) .075(3)
C(16)A 1.1443(3) .1034(2) .5149(6) .054(2)
C(17)A 1.1358(4) .1498(2) .4084(7) .069(2)
C(18)A 1.1944(5) .1705(3) .3144(8) .089(3)
C(19)A 1.2610(5) .1440(4) .3312(10) .091(4)
C(20)A 1.2695(4) .0974(4) .4355(10) .087(3)
C(21)A 1.2120(4) .0773(3) .5269(8) .067(3)
N(22)A 1.0164(3) .0570(3) .3933(10) .146(3)
O(23)A .9544(4) .0563(2) .3698(6) .124(3)
C(1)B .6329(3) .0978(2) .3758(7) .063(2)
C(2)B .6583(3) .1231(2) .1997(7) .058(2)
N(3)B .5976(2) .1501(2) .0969(5) .057(2)
C(4)B .5310(3) .1728(2) .1736(7) .061(2)
C(5)B .5132(3) .1431(3) .3511(7) .069(3)
C(6)B .4768(4) .0862(3) .3302(10) .083(3)
C(7)B .5259(4) .0417(3) .2597(10) .073(3)
C(8)B .5984(4) .0404(3) .3590(10) .075(3)
C(9)B .5829(4) .1384(3) .4641(8) .072(3)
C(10)B .7007(3) .0823(2) .0918(7) .054(2)
C(11)B .7713(4) .0703(3) .1452(8) .062(3)
C(12)B .8106(4) .0311(3) .0577(10) .078(3)
C(13)B .7813(5) .0034(3) -.0862(10) .085(3)
C(14)B .7115(5) .0153(3) -.1419(10) .095(3)
C(15)B .6727(4) .0543(3) -.0550(8) .074(3)
C(16)B .4663(3) .1734(2) .0456(7) .059(2)
C(17)B .4522(4) .1326(3) -.0793(8) .082(3)
C(18)B .3881(5) .1333(4) -.1806(10) .098(4)
C(19)B .3380(4) .1742(4) -.1553(12) .099(4)
C(20)B .3522(5) .2154(4) -.0345(11) .088(4)
C(21)B .4160(4) .2148(3) .0652(8) .071(3)
N(22)B .6330(3) .1775(2) -.0469(7) .094(2)
O(23)B .5928(3) .2111(2) -.1025(6) .107(2)
H(1)A .930(3) .1020(19) .927(6) .060(17)
H(2)A .922(3) .054(2) .671(6) .082(16)
H(4)A 1.092(2) .0371(18) .634(5) .064(14)
H(5)A 1.144(3) .0871(18) .871(6) .067(16)
H(61)A 1.127(3) .177(2) .960(8) .11(2)
H(62)A 1.151(3) .1820(18) .771(6) .056(16)
H(71)A 1.035(3) .201(2) .660(7) .09(2)
H(72)A 1.053(3) .243(2) .819(6) .093(18)
H(81)A .986(3) .188(2) 1.026(8) .11(2)
H(82)A .932(3) .199(2) .873(7) .10(2)
H(91)A 1.029(3) .036(2) .925(7) .11(2)
H(92)A 1.046(3) .089(2) 1.053(7) .088(19)
H(11)A .947(3) .1700(19) .384(6) .061(19)
H(12)A .860(3) .228(2) .273(7) .09(2)
H(13)A .744(3) .235(2) .426(8) .11(3)
H(14)A .732(3) .181(2) .666(6) .06(2)
H(15)A .815(3) .1208(18) .755(6) .045(19)
H(17)A 1.085(3) .1694(17) .395(5) .051(14)
H(18)A 1.183(4) .206(3) .238(8) .14(3)
H(19)A 1.298(3) .162(2) .263(7) .11(3)
H(20)A 1.319(5) .070(3) .4532(10) .21(4)
H(21)A 1.219(3) .039(2) .611(6) .085(17)
H(1)B .677(2) .0923(16) .451(5) .051(14)
H(2)B .689(2) .1536(16) .237(5) .039(13)
H(4)B .540(3) .214(2) .193(6) .079(17)
H(5)B .480(2) .1698(18) .409(6) .061(15)
H(61)B .434(3) .087(2) .256(7) .08(2)
H(62)B .464(3) .074(2) .443(7) .075(18)
H(71)B .502(3) .003(2) .261(6) .087(19)
H(72)B .532(3) .0424(18) .124(7) .072(17)
H(81)B .634(3) .014(2) .297(6) .074(18)
H(82)B .591(3) .0280(19) .473(7) .067(18)
H(91)B .569(3) .1266(19) .583(7) .081(18)
H(92) .609(3) .179(2) .489(6) .084(18)
H(11)B .791(2) .0900(17) .237(5) .043(15)
H(12)B .857(2) .0266(17) .094(5) .042(16)
H(13)B .818(3) -.020(2) -.147(8) .12(3)
H(14)B .697(3) -.001(3) -.253(8) .11(3)
H(15)B .624(3) .0605(17) -.087(6) .051(16)
H(17)B .486(3) .1048(19) -.098(6) .063(18)
H(18)B .375(3) .103(3) -.251(8) .11(3)
H(19)B .292(3) .177(2) -.209(7) .10(2)
H(20)B .316(3) .243(2) -.010(7) .10(2)
H(21)B .427(3) .245(2) .148(6) .071(18)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(11)A C(12)A C(13)A 121.4(7) yes
C(12)A C(13)A C(14)A 118.9(8) yes
C(13)A C(14)A C(15)A 120.6(7) yes
C(14)A C(15)A C(10)A 121.3(7) yes
C(15)A C(10)A C(11)A 117.8(6) yes
C(4)A C(16)A C(17)A 124.2(5) yes
C(4)A C(16)A C(21)A 116.4(5) yes
C(16)A C(17)A C(18)A 120.4(6) yes
C(17)A C(18)A C(19)A 119.0(7) yes
C(18)A C(19)A C(20)A 120.8(8) yes
C(19)A C(20)A C(21)A 119.9(8) yes
C(20)A C(21)A C(16)A 120.8(6) yes
C(21)A C(16)A C(17)A 119.1(5) yes
C(1)A C(2)A N(3)A 111.3(4) yes
C(2)A N(3)A C(4)A 126.4(4) yes
N(3)A C(4)A C(5)A 111.9(4) yes
C(4)A C(5)A C(6)A 115.8(5) yes
C(5)A C(6)A C(7)A 112.6(6) yes
C(6)A C(7)A C(8)A 110.3(6) yes
C(7)A C(8)A C(1)A 112.5(6) yes
C(8)A C(1)A C(9)A 111.1(6) yes
C(1)A C(9)A C(5)A 107.5(5) yes
C(9)A C(5)A C(4)A 108.0(5) yes
C(9)A C(5)A C(6)A 112.0(5) yes
C(2)A C(1)A C(8)A 114.5(5) yes
C(2)A C(1)A C(9)A 109.8(5) yes
C(1)A C(2)A C(10)A 112.3(5) yes
C(2)A N(3)A N(22)A 126.4(4) yes
C(4)A N(3)A N(22)A 99.0(4) yes
N(3)A C(4) C(16)A 114.2(4) yes
C(5)A C(4)A C(16)A 111.6(4) yes
N(3)A N(22)A O(23)A 93.8(5) yes
N(3)A C(2)A C(10)A 112.7(4) yes
C(2)A C(10)A C(15)A 117.3(5) yes
C(2)A C(10)A C(11)A 124.9(5) yes
C(10)A C(11)A C(12)A 120.0(6) yes
C(11)B C(12)B C(13)B 121.0(7) yes
C(12)B C(13)B C(14)B 118.9(7) yes
C(13)B C(14)B C(15)B 120.0(7) yes
C(14)B C(15)B C(10)B 122.2(6) yes
C(15)B C(10)B C(11)B 117.1(5) yes
C(4)B C(16)B C(17)B 123.8(5) yes
C(4)B C(16)B C(21)B 117.4(5) yes
C(16)B C(17)B C(18)B 120.4(7) yes
C(17)B C(18)B C(19)B 120.0(8) yes
C(18)B C(19)B C(20)B 120.0(8) yes
C(19)B C(20)B C(21)B 120.0(8) yes
C(20)B C(21)B C(16)B 121.2(7) yes
C(21)B C(16)B C(17)B 118.5(6) yes
C(1)B C(2)B N(3)B 112.0(4) yes
C(2)B N(3)B C(4)B 125.3(4) yes
N(3)B C(4)B C(5)B 111.4(4) yes
C(4)B C(5)B C(6)B 115.2(5) yes
C(5)B C(6)B C(7)B 113.9(6) yes
C(6)B C(7)B C(8)B 111.8(6) yes
C(7)B C(8)B C(1)B 112.5(6) yes
C(8)B C(1)B C(9)B 111.3(5) yes
C(1)B C(9)B C(5)B 108.5(5) yes
C(9)B C(5)B C(4)B 108.5(5) yes
C(9)B C(5)B C(6)B 110.5(5) yes
C(2)B C(1)B C(8)B 115.0(5) yes
C(2)B C(1)B C(9)B 109.2(5) yes
C(1)B C(2)B C(10)B 112.4(4) yes
C(2)B N(3)B N(22)B 103.9(4) yes
C(4)B N(3)B N(22)B 121.7(4) yes
N(3)B C(4)B C(16)B 113.8(4) yes
C(5)B C(4)B C(16)B 111.6(4) yes
N(3)B N(22)B O(23)B 106.8(5) yes
N(3)B C(2)B C(10)B 113.4(4) yes
C(2)B C(10)B C(15)B 124.2(5) yes
C(2)B C(10)B C(11)B 118.6(5) yes
C(10)B C(11)B C(12)B 120.8(6) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1)A C(2)A 1.547(8) yes
C(2)A N(3)A 1.497(6) yes
N(3)A C(4)A 1.468(7) yes
C(4)A C(5)A 1.532(8) yes
C(5)A C(6)A 1.537(10) yes
C(6)A C(7)A 1.534(10) yes
C(7)A C(8)A 1.493(11) yes
C(8)A C(1)A 1.527(10) yes
C(1)A C(9)A 1.519(9) yes
C(5)A C(9)A 1.519(8) yes
C(2)A C(10)A 1.529(7) yes
C(4)A C(16)A 1.504(7) yes
N(3)A N(22)A 1.542(8) yes
N(22)A O(23)A 1.152(9) yes
C(10)A C(11)A 1.379(8) yes
C(11)A C(12)A 1.394(10) yes
C(12)A C(13)A 1.354(13) yes
C(13)A C(14)A 1.361(12) yes
C(14)A C(15)A 1.380(11) yes
C(10)A C(15)A 1.378(9) yes
C(16)A C(17)A 1.383(7) yes
C(17)A C(18)A 1.403(11) yes
C(18)A C(19)A 1.387(13) yes
C(19)A C(20)A 1.377(13) yes
C(20)A C(21)A 1.372(11) yes
C(16)A C(21)A 1.399(9) yes
C(1)B C(2)B 1.547(7) yes
C(2)B N(3)B 1.491(7) yes
N(3)B C(4)B 1.479(7) yes
C(4)B C(5)B 1.562(8) yes
C(5)B C(6)B 1.533(10) yes
C(6)B C(7)B 1.511(10) yes
C(7)B C(8)B 1.512(11) yes
C(8)B C(1)B 1.526(9) yes
C(1)B C(9)B 1.514(9) yes
C(5)B C(9)B 1.524(9) yes
C(2)B C(10)B 1.510(7) yes
C(4)B C(16)B 1.511(8) yes
N(3)B N(22)B 1.443(7) yes
N(22)B O(23)B 1.167(7) yes
C(10)B C(11)B 1.382(9) yes
C(11)B C(12)B 1.373(10) yes
C(12)B C(13)B 1.370(11) yes
C(13)B C(14)B 1.372(13) yes
C(14)B C(15)B 1.362(11) yes
C(10)B C(15)B 1.382(8) yes
C(16)B C(17)B 1.381(8) yes
C(17)B C(18)B 1.387(11) yes
C(18)B C(19)B 1.369(13) yes
C(19)B C(20)B 1.367(13) yes
C(20)B C(21)B 1.377(11) yes
C(16)B C(21)B 1.374(9) yes
