#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/00/2200028.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_2200028
loop_
_publ_author_name
'Taylor, Max R.'
'Thompson, Malcolm J.'
_publ_section_title
;
 4-Nitrophenanthrene
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o9
_journal_page_last               o10
_journal_paper_doi               10.1107/S1600536800018766
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C14 H9 N1 O2'
_chemical_formula_moiety         'C14 H9 N1 O2'
_chemical_formula_sum            'C14 H9 N O2'
_chemical_formula_weight         223.23
_chemical_melting_point          354.9(3)
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 109.730(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.061(2)
_cell_length_b                   12.449(3)
_cell_length_c                   11.132(3)
_cell_measurement_reflns_used    5719
_cell_measurement_temperature    168(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      2.5
_cell_volume                     1051.5(5)
_computing_cell_refinement       'SAINT (Bruker, 1996)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction
'SAINT and Xtal3.4 ADDREF SORTRF (Hall et al., 1995)'
_computing_molecular_graphics    Xtal3.4
_computing_publication_material  'Xtal3.4 BONDLA CIFIO'
_computing_structure_refinement  'Xtal3.4 CRYLSQ'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      168(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measurement_device_type  'Bruker SMART P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .028
_diffrn_reflns_av_sigmaI/netI    .078
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13110
_diffrn_reflns_theta_max         26.4
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .10
_exptl_absorpt_correction_T_max  .98
_exptl_absorpt_correction_T_min  .78
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.41
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          .72
_exptl_crystal_size_mid          .46
_exptl_crystal_size_min          .26
_refine_diff_density_max         .29
_refine_diff_density_min         -.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.03
_refine_ls_goodness_of_fit_ref   .99
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1943
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .058
_refine_ls_R_factor_gt           .049
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w = 1/[\s^2^(Fo^2^)+(0.06Fo^2^)^2^+0.5Fo^2^]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .12
_refine_ls_wR_factor_ref         .11
_reflns_number_gt                1945
_reflns_number_total             2135
_reflns_threshold_expression     Fsqd>0
_cod_data_source_file            cf6012.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '81.5-82.0\%C' was changed to
'354.9(3)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '81.5-82.0 \%C' was changed to
'354.9(3)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     -p_2ybc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C14 H9 N1 O2'
_cod_database_code               2200028
_cod_database_fobs_code          2200028
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,1/2+y,1/2-z
-x,-y,-z
+x,1/2-y,1/2+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_calc_flag
_atom_site_calc_attached_atom
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N .75013(19) .30657(11) .08041(14) .0377(7) Uani ? ? 1.00000 ? ?
O1 .85095(16) .25134(10) .04507(13) .0487(7) Uani ? ? 1.00000 ? ?
O2 .79833(18) .38205(11) .15553(15) .0598(8) Uani ? ? 1.00000 ? ?
C1 .2069(2) .25122(14) -.10627(17) .0390(8) Uani ? ? 1.00000 ? ?
C2 .2871(3) .34201(15) -.12965(17) .0426(9) Uani ? ? 1.00000 ? ?
C3 .4662(2) .35883(14) -.06233(17) .0384(8) Uani ? ? 1.00000 ? ?
C4 .5578(2) .28431(12) .02590(15) .0319(7) Uani ? ? 1.00000 ? ?
C5 .7442(2) .12262(14) .24429(16) .0361(8) Uani ? ? 1.00000 ? ?
C6 .8270(2) .04098(15) .32569(17) .0417(9) Uani ? ? 1.00000 ? ?
C7 .7421(2) -.05733(14) .32257(16) .0396(8) Uani ? ? 1.00000 ? ?
C8 .5714(2) -.06978(13) .24207(16) .0347(8) Uani ? ? 1.00000 ? ?
C9 .3012(2) -.00034(13) .07995(16) .0345(8) Uani ? ? 1.00000 ? ?
C10 .2131(2) .07775(14) .00120(16) .0361(8) Uani ? ? 1.00000 ? ?
C4a .4819(2) .19059(11) .05832(14) .0275(7) Uani ? ? 1.00000 ? ?
C4b .5727(2) .11059(12) .15396(14) .0278(7) Uani ? ? 1.00000 ? ?
C8a .4823(2) .01289(12) .15837(14) .0288(7) Uani ? ? 1.00000 ? ?
C10a .2999(2) .17500(12) -.01412(15) .0316(7) Uani ? ? 1.00000 ? ?
H1 .084(3) .2316(15) -.1558(18) .043(5) Uiso ? ? 1.00000 ? ?
H2 .223(3) .3906(17) -.1983(19) .053(6) Uiso ? ? 1.00000 ? ?
H3 .525(2) .4204(16) -.0779(17) .045(5) Uiso ? ? 1.00000 ? ?
H5 .803(3) .1915(16) .2473(19) .053(6) Uiso ? ? 1.00000 ? ?
H6 .949(3) .0541(15) .3881(18) .048(5) Uiso ? ? 1.00000 ? ?
H7 .800(2) -.1151(16) .3780(18) .050(5) Uiso ? ? 1.00000 ? ?
H8 .506(2) -.1367(15) .2402(18) .041(5) Uiso ? ? 1.00000 ? ?
H9 .248(2) -.0656(16) .0863(18) .045(5) Uiso ? ? 1.00000 ? ?
H10 .092(3) .0680(16) -.0524(19) .053(6) Uiso ? ? 1.00000 ? ?
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N .0414(8) .0293(7) .0454(8) -.0073(6) .0185(7) .0006(6)
O1 .0415(7) .0457(7) .0650(9) -.0015(6) .0261(6) -.0029(6)
O2 .0559(9) .0433(8) .0777(10) -.0171(6) .0194(7) -.0218(7)
C1 .0337(9) .0437(10) .0396(9) .0094(8) .0122(7) .0005(8)
C2 .0525(11) .0386(10) .0392(9) .0151(8) .0188(8) .0088(8)
C3 .0509(10) .0282(8) .0429(9) .0036(7) .0250(8) .0041(7)
C4 .0355(9) .0275(8) .0363(9) -.0009(6) .0169(7) -.0028(7)
C5 .0341(9) .0362(9) .0371(9) -.0065(7) .0108(7) .0026(7)
C6 .0343(9) .0514(11) .0370(9) .0010(8) .0090(7) .0061(8)
C7 .0474(10) .0380(9) .0362(9) .0109(8) .0179(8) .0074(8)
C8 .0462(10) .0262(8) .0384(9) -.0002(7) .0231(8) .0007(7)
C9 .0354(9) .0289(8) .0439(9) -.0083(7) .0195(7) -.0051(7)
C10 .0276(8) .0385(9) .0439(9) -.0041(7) .0142(7) -.0063(8)
C4a .0321(8) .0234(7) .0301(8) -.0007(6) .0146(6) -.0042(6)
C4b .0292(8) .0275(8) .0296(7) -.0008(6) .0137(6) -.0026(6)
C8a .0338(8) .0261(7) .0312(8) -.0015(6) .0170(6) -.0030(6)
C10a .0318(8) .0315(8) .0338(8) .0034(6) .0140(7) -.0028(7)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .002 .002 'Int Tables Vol IV Tables 2.2B and 2.3.1'
H 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1'
N .004 .003 'Int Tables Vol IV Tables 2.2B and 2.3.1'
O .008 .006 'Int Tables Vol IV Tables 2.2B and 2.3.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 N O2 123.69(15)
O1 N C4 118.49(13)
O2 N C4 117.77(15)
C2 C1 C10a 121.55(15)
C2 C1 H1 123.1(11)
C10a C1 H1 115.2(11)
C1 C2 C3 119.29(16)
C1 C2 H2 120.0(12)
C3 C2 H2 120.4(12)
C2 C3 C4 119.40(17)
C2 C3 H3 120.9(10)
C4 C3 H3 119.7(10)
N C4 C3 113.66(15)
N C4 C4a 121.92(12)
C3 C4 C4a 124.32(14)
C6 C5 C4b 122.00(16)
C6 C5 H5 120.2(10)
C4b C5 H5 117.8(10)
C5 C6 C7 120.42(15)
C5 C6 H6 118.6(11)
C7 C6 H6 121.0(11)
C6 C7 C8 119.30(15)
C6 C7 H7 120.8(11)
C8 C7 H7 119.8(11)
C7 C8 C8a 121.54(15)
C7 C8 H8 121.5(10)
C8a C8 H8 117.0(10)
C10 C9 C8a 121.33(15)
C10 C9 H9 121.6(10)
C8a C9 H9 117.0(10)
C9 C10 C10a 121.10(14)
C9 C10 H10 121.0(12)
C10a C10 H10 117.7(12)
C4 C4a C4b 126.35(13)
C4 C4a C10a 114.63(12)
C4b C4a C10a 119.01(14)
C5 C4b C4a 125.02(14)
C5 C4b C8a 116.94(13)
C4a C4b C8a 118.04(12)
C8 C8a C9 120.31(15)
C8 C8a C4b 119.47(13)
C9 C8a C4b 120.21(13)
C1 C10a C10 119.43(13)
C1 C10a C4a 120.73(15)
C10 C10a C4a 119.74(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N O1 . . 1.226(2) y
N O2 . . 1.230(2) y
N C4 . . 1.488(2) y
C1 C2 . . 1.370(3) ?
C1 C10a . . 1.413(2) ?
C1 H1 . . .990(18) ?
C2 C3 . . 1.400(3) ?
C2 H2 . . .976(19) ?
C3 C4 . . 1.371(2) y
C3 H3 . . .95(2) ?
C4 C4a . . 1.420(2) y
C5 C6 . . 1.375(2) ?
C5 C4b . . 1.417(2) ?
C5 H5 . . .98(2) ?
C6 C7 . . 1.397(3) ?
C6 H6 . . 1.009(18) ?
C7 C8 . . 1.374(2) ?
C7 H7 . . .96(2) ?
C8 C8a . . 1.411(2) ?
C8 H8 . . .98(2) ?
C9 C10 . . 1.341(2) ?
C9 C8a . . 1.435(2) ?
C9 H9 . . .93(2) ?
C10 C10a . . 1.437(2) ?
C10 H10 . . .966(18) ?
C4a C4b . . 1.461(2) ?
C4a C10a . . 1.428(2) ?
C4b C8a . . 1.427(2) ?