#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/24/2012402.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_2012402
loop_
_publ_author_name
'Sekine, Akiko'
'Uekusa, Hidehiro'
'Ohashi, Yuji'
'Yoshimura, Kimihiro'
'Yagi, Mikio'
'Higuchi, Jiro'
_publ_section_title
;
 4-Nitro-9,10-dihydrophenanthrene and a polymorphic form of
 4-nitrophenanthrene
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1462
_journal_page_last               1464
_journal_paper_doi               10.1107/S0108270101017474
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C14 H9 N O2'
_chemical_formula_moiety         'C14 H9 N O2'
_chemical_formula_sum            'C14 H9 N O2'
_chemical_formula_weight         223.22
_chemical_name_systematic
;
 ?
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 110.48(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.934(7)
_cell_length_b                   12.471(5)
_cell_length_c                   11.436(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      60.0
_cell_measurement_theta_min      55.0
_cell_volume                     2128.8(17)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993a)
;
_computing_data_reduction
;
TEXSAN (Molecular Structure Corporation, 1993b)'
;
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Riguak AFC-7S'
_diffrn_measurement_method       θ-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0299
_diffrn_reflns_av_sigmaI/netI    .0450
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3583
_diffrn_reflns_theta_full        24.13
_diffrn_reflns_theta_max         24.13
_diffrn_reflns_theta_min         1.36
_diffrn_standards_decay_%        .2
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .094
_exptl_absorpt_correction_T_max  .972
_exptl_absorpt_correction_T_min  .797
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968).'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             928
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .3
_refine_diff_density_max         .217
_refine_diff_density_min         -.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.038
_refine_ls_goodness_of_fit_obs   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_restrained_S_obs      1.117
_refine_ls_R_factor_all          .0976
_refine_ls_R_factor_obs          .0539
_refine_ls_shift/esd_max         .001
_refine_ls_shift/esd_mean        .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[s²(Fo²)+(0.0868P)²+0.2279P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .1634
_refine_ls_wR_factor_obs         .1395
_reflns_number_observed          2240
_reflns_number_total             3398
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            ta1338.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2129.0(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2012402
_cod_database_fobs_code          2012402
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'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
N1 .6026(2) .3115(2) 1.0396(2) .0552(6) Uani d . 1 . N
O1 .65477(15) .2549(2) 1.1180(2) .0719(7) Uani d . 1 . O
O2 .6251(2) .3922(2) .9962(2) .0805(7) Uani d . 1 . O
C1 .3289(2) .2457(3) .9488(3) .0589(8) Uani d . 1 . C
H1 .2685 .2322 .9328 .071 Uiso calc R 1 . H
C2 .3664(2) .3368(3) 1.0105(3) .0652(9) Uani d . 1 . C
H2 .3316 .3854 1.0352 .078 Uiso calc R 1 . H
C3 .4567(2) .3571(3) 1.0365(3) .0596(8) Uani d . 1 . C
H3 .4830 .4184 1.0804 .072 Uiso calc R 1 . H
C4 .5067(2) .2858(2) .9970(2) .0467(6) Uani d . 1 . C
C4a .4712(2) .1907(2) .9282(2) .0417(6) Uani d . 1 . C
C4b .5204(2) .1149(2) .8791(2) .0422(6) Uani d . 1 . C
C5 .6061(2) .1335(2) .8722(2) .0494(7) Uani d . 1 . C
H5 .6341 .1990 .8989 .059 Uiso calc R 1 . H
C6 .6487(2) .0574(3) .8270(3) .0592(8) Uani d . 1 . C
H6 .7048 .0721 .8227 .071 Uiso calc R 1 . H
C7 .6090(2) -.0417(3) .7875(3) .0619(8) Uani d . 1 . C
H7 .6394 -.0942 .7604 .074 Uiso calc R 1 . H
C8 .5256(2) -.0614(2) .7887(3) .0583(8) Uani d . 1 . C
H8 .4991 -.1277 .7614 .070 Uiso calc R 1 . H
C8a .4779(2) .0159(2) .8303(2) .0464(6) Uani d . 1 . C
C9 .3874(2) -.0020(2) .8184(3) .0562(7) Uani d . 1 . C
H9 .3604 -.0669 .7863 .067 Uiso calc R 1 . H
C10 .3398(2) .0726(2) .8523(3) .0557(7) Uani d . 1 . C
H10 .2797 .0601 .8391 .067 Uiso calc R 1 . H
C10a .3801(2) .1710(2) .9086(2) .0477(7) Uani d . 1 . C
N11 .8639(2) .3028(2) .9130(3) .0639(7) Uani d . 1 . N
O11 .8352(2) .3760(2) .8385(3) .1024(10) Uani d . 1 . O
O12 .8162(2) .2440(2) .9473(3) .0859(8) Uani d . 1 . O
C11 1.1404(2) .2669(3) 1.0986(3) .0620(8) Uani d . 1 . C
H11 1.2011 .2598 1.1446 .074 Uiso calc R 1 . H
C12 1.0952(2) .3554(3) 1.1156(3) .0694(9) Uani d . 1 . C
H12 1.1254 .4091 1.1708 .083 Uiso calc R 1 . H
C13 1.0047(2) .3643(2) 1.0506(3) .0630(8) Uani d . 1 . C
H13 .9731 .4230 1.0637 .076 Uiso calc R 1 . H
C14 .9615(2) .2871(2) .9669(3) .0493(7) Uani d . 1 . C
C14a 1.0042(2) .1953(2) .9402(2) .0433(6) Uani d . 1 . C
C14b .9618(2) .1122(2) .8481(2) .0423(6) Uani d . 1 . C
C15 .8750(2) .1185(2) .7578(3) .0529(7) Uani d . 1 . C
H15 .8420 .1811 .7516 .064 Uiso calc R 1 . H
C16 .8379(2) .0348(3) .6789(3) .0617(8) Uani d . 1 . C
H16 .7804 .0413 .6203 .074 Uiso calc R 1 . H
C17 .8856(2) -.0598(3) .6857(3) .0637(8) Uani d . 1 . C
H17 .8592 -.1178 .6351 .076 Uiso calc R 1 . H
C18 .9710(2) -.0669(2) .7668(3) .0565(8) Uani d . 1 . C
H18 1.0034 -.1293 .7691 .068 Uiso calc R 1 . H
C18a 1.0118(2) .0184(2) .8480(2) .0466(6) Uani d . 1 . C
C19 1.1037(2) .0108(2) .9271(3) .0531(7) Uani d . 1 . C
H19 1.1357 -.0514 .9265 .064 Uiso calc R 1 . H
C20 1.1441(2) .0922(2) 1.0019(3) .0543(7) Uani d . 1 . C
H20 1.2049 .0872 1.0484 .065 Uiso calc R 1 . H
C20a 1.0963(2) .1861(2) 1.0122(2) .0475(7) Uani d . 1 . C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O1 N1 O2 123.6(3) y
O1 N1 C4 118.9(2) y
O2 N1 C4 117.4(2) y
C3 C4 C4a 123.9(3) y
C3 C4 N1 114.1(3) y
C4a C4 N1 121.9(2) y
C4 C3 C2 119.3(3) ?
C1 C2 C3 119.9(3) ?
C2 C1 C10a 121.2(3) ?
C4a C10a C1 120.8(3) ?
C4a C10a C10 119.8(3) ?
C1 C10a C10 119.4(3) ?
C9 C10 C10a 121.1(3) ?
C10 C9 C8a 121.5(3) ?
C8 C8a C9 120.6(3) ?
C8 C8a C4b 119.2(3) ?
C9 C8a C4b 120.1(3) ?
C7 C8 C8a 121.6(3) ?
C8 C7 C6 119.7(3) ?
C5 C6 C7 120.6(3) ?
C6 C5 C4b 121.6(3) ?
C5 C4b C8a 117.1(2) ?
C5 C4b C4a 125.0(2) ?
C8a C4b C4a 117.8(2) ?
C10a C4a C4 114.8(2) ?
C10a C4a C4b 119.1(2) ?
C4 C4a C4b 126.1(2) ?
O12 N11 O11 123.4(3) y
O12 N11 C14 118.2(3) y
O11 N11 C14 118.3(3) y
C13 C14 C14a 124.0(3) y
C13 C14 N11 113.6(3) y
C14a C14 N11 122.3(2) y
C14 C13 C12 119.9(3) ?
C11 C12 C13 119.5(3) ?
C12 C11 C20a 121.1(3) ?
C11 C20a C14a 120.7(3) ?
C11 C20a C20 119.7(3) ?
C14a C20a C20 119.6(3) ?
C19 C20 C20a 121.7(3) ?
C20 C19 C18a 120.8(3) ?
C18 C18a C14b 119.5(3) ?
C18 C18a C19 120.0(3) ?
C14b C18a C19 120.4(3) ?
C17 C18 C18a 121.5(3) ?
C18 C17 C16 119.5(3) ?
C15 C16 C17 120.5(3) ?
C16 C15 C14b 121.7(3) ?
C15 C14b C18a 117.0(2) ?
C15 C14b C14a 125.1(2) ?
C18a C14b C14a 117.8(2) ?
C20a C14a C14 114.7(3) ?
C20a C14a C14b 119.1(2) ?
C14 C14a C14b 126.2(2) ?
C14 C13 H13 120.04 ?
C11 C12 H12 120.26 ?
C20a C20 H20 119.22 ?
C18a C19 H19 119.58 ?
C18 C17 H17 120.16 ?
C15 C16 H16 119.80 ?
C4 C3 H3 120.45 ?
C1 C2 H2 120.11 ?
C10a C10 H10 119.49 ?
C8a C9 H9 119.31 ?
C8 C7 H7 120.16 ?
C5 C6 H6 119.72 ?
C12 C13 H13 120.04 ?
C12 C11 H11 119.44 ?
C19 C20 H20 119.11 ?
C18a C18 H18 119.27 ?
C16 C17 H17 120.38 ?
C16 C15 H15 119.13 ?
C2 C3 H3 120.23 ?
C2 C1 H1 119.32 ?
C9 C10 H10 119.47 ?
C8a C8 H8 119.06 ?
C6 C7 H7 120.24 ?
C6 C5 H5 119.26 ?
C13 C12 H12 120.25 ?
C20a C11 H11 119.46 ?
C20 C19 H19 119.68 ?
C17 C18 H18 119.28 ?
C17 C16 H16 119.70 ?
C14b C15 H15 119.11 ?
C3 C2 H2 120.02 ?
C10a C1 H1 119.40 ?
C10 C9 H9 119.20 ?
C7 C8 H8 119.24 ?
C7 C6 H6 119.63 ?
C4b C5 H5 119.18 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 O1 . 1.213(3) y
N1 O2 . 1.230(3) y
N1 C4 . 1.468(4) y
C4 C3 . 1.371(4) y
C4 C4a . 1.427(4) y
C3 C2 . 1.386(4) ?
C2 C1 . 1.360(4) ?
C1 C10a . 1.418(4) ?
C10a C4a . 1.411(4) ?
C10a C10 . 1.430(4) ?
C10 C9 . 1.339(4) ?
C9 C8a . 1.419(4) ?
C8a C8 . 1.409(4) ?
C8a C4b . 1.424(4) ?
C8 C7 . 1.357(4) ?
C7 C6 . 1.390(4) ?
C6 C5 . 1.370(4) ?
C5 C4b . 1.414(4) ?
C4a C4b . 1.460(4) y
N11 O11 . 1.223(4) y
N11 O12 . 1.217(3) y
N11 C14 . 1.471(4) y
C14 C13 . 1.363(4) y
C14 C14a . 1.418(4) y
C13 C12 . 1.376(5) ?
C12 C11 . 1.369(5) ?
C11 C20a . 1.413(4) ?
C20a C14a . 1.414(4) ?
C20a C20 . 1.424(4) ?
C20 C19 . 1.339(4) ?
C19 C18a . 1.429(4) ?
C18a C18 . 1.412(4) ?
C18a C14b . 1.416(4) ?
C18 C17 . 1.355(4) ?
C17 C16 . 1.391(4) ?
C16 C15 . 1.372(4) ?
C15 C14b . 1.409(4) ?
C14b C14a . 1.464(4) y
C13 H13 . .93 ?
C12 H12 . .93 ?
C11 H11 . .93 ?
C20 H20 . .93 ?
C19 H19 . .93 ?
C18 H18 . .93 ?
C17 H17 . .93 ?
C16 H16 . .93 ?
C15 H15 . .93 ?
C3 H3 . .93 ?
C2 H2 . .93 ?
C1 H1 . .93 ?
C10 H10 . .93 ?
C9 H9 . .93 ?
C8 H8 . .93 ?
C7 H7 . .93 ?
C6 H6 . .93 ?
C5 H5 . .93 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 139042
