#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/33/2223341.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_2223341
loop_
_publ_author_name
'Jing, Lin-Hai'
_publ_section_title
;
 (E)-1-(2-Nitroethenyl)naphthalene
;
_journal_coeditor_code           CI2915
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2521
_journal_paper_doi               10.1107/S1600536809037623
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H9 N O2'
_chemical_formula_moiety         'C12 H9 N O2'
_chemical_formula_sum            'C12 H9 N O2'
_chemical_formula_weight         199.20
_chemical_name_systematic
;
(E)-1-(2-Nitroethenyl)naphthalene
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.2670(14)
_cell_length_b                   13.741(3)
_cell_length_c                   19.127(4)
_cell_measurement_reflns_used    5654
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.00
_cell_volume                     1909.9(7)
_computing_cell_refinement       'RAPID-AUTO (Rigaku/MSC, 2004)'
_computing_data_collection       'RAPID-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'RAPID-AUTO (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku SPIDER'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14290
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.202
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0285P)²+1.6P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                2019
_reflns_number_total             2179
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2915.cif
_cod_data_source_block           I
_cod_original_cell_volume        1909.9(6)
_cod_database_code               2223341
_cod_database_fobs_code          2223341
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.4804(2) 0.25001(8) 0.56207(6) 0.0438(4) Uani d . 1 . .
O O2 0.4755(2) 0.35241(8) 0.47651(6) 0.0414(3) Uani d . 1 . .
N N1 0.50070(19) 0.33185(9) 0.53854(6) 0.0270(3) Uani d . 1 . .
C C1 0.61925(19) 0.47388(10) 0.70231(7) 0.0193(3) Uani d . 1 . .
C C2 0.67974(19) 0.56401(10) 0.67959(8) 0.0216(3) Uani d . 1 . .
H H2 0.6907 0.5759 0.6308 0.026 Uiso calc R 1 . .
C C3 0.7251(2) 0.63794(10) 0.72673(8) 0.0233(3) Uani d . 1 . .
H H3 0.7665 0.6991 0.7097 0.028 Uiso calc R 1 . .
C C4 0.7103(2) 0.62294(10) 0.79730(8) 0.0237(3) Uani d . 1 . .
H H4 0.7403 0.6740 0.8288 0.028 Uiso calc R 1 . .
C C5 0.6346(2) 0.51571(11) 0.89674(8) 0.0250(3) Uani d . 1 . .
H H5 0.6628 0.5669 0.9283 0.030 Uiso calc R 1 . .
C C6 0.5794(2) 0.42761(11) 0.92232(8) 0.0260(3) Uani d . 1 . .
H H6 0.5693 0.4178 0.9713 0.031 Uiso calc R 1 . .
C C7 0.5373(2) 0.35112(11) 0.87574(8) 0.0246(3) Uani d . 1 . .
H H7 0.5001 0.2897 0.8936 0.030 Uiso calc R 1 . .
C C8 0.5497(2) 0.36480(10) 0.80489(7) 0.0216(3) Uani d . 1 . .
H H8 0.5198 0.3126 0.7744 0.026 Uiso calc R 1 . .
C C9 0.60624(18) 0.45543(9) 0.77616(7) 0.0189(3) Uani d . 1 . .
C C10 0.65057(19) 0.53203(10) 0.82360(8) 0.0204(3) Uani d . 1 . .
C C11 0.5682(2) 0.39854(10) 0.65200(7) 0.0219(3) Uani d . 1 . .
H H11 0.5419 0.3356 0.6700 0.026 Uiso calc R 1 . .
C C12 0.5554(2) 0.41047(11) 0.58392(8) 0.0278(3) Uani d . 1 . .
H H12 0.5829 0.4723 0.5642 0.033 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 N1 O2 . . 123.23(13) ?
O1 N1 C12 . . 120.13(13) ?
O2 N1 C12 . . 116.64(12) ?
C2 C1 C9 . . 119.15(13) ?
C2 C1 C11 . . 120.51(13) ?
C9 C1 C11 . . 120.34(12) ?
C1 C2 C3 . . 121.50(13) ?
C1 C2 H2 . . 119.3 ?
C3 C2 H2 . . 119.3 ?
C4 C3 C2 . . 120.52(13) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C10 . . 120.48(13) ?
C3 C4 H4 . . 119.8 ?
C10 C4 H4 . . 119.8 ?
C6 C5 C10 . . 121.07(14) ?
C6 C5 H5 . . 119.5 ?
C10 C5 H5 . . 119.5 ?
C5 C6 C7 . . 119.84(14) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C8 C7 C6 . . 120.51(14) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C7 C8 C9 . . 121.40(13) ?
C7 C8 H8 . . 119.3 ?
C9 C8 H8 . . 119.3 ?
C8 C9 C10 . . 117.75(13) ?
C8 C9 C1 . . 123.58(13) ?
C10 C9 C1 . . 118.67(13) ?
C4 C10 C5 . . 120.94(13) ?
C4 C10 C9 . . 119.65(13) ?
C5 C10 C9 . . 119.42(13) ?
C12 C11 C1 . . 125.55(13) ?
C12 C11 H11 . . 117.2 ?
C1 C11 H11 . . 117.2 ?
C11 C12 N1 . . 121.46(14) ?
C11 C12 H12 . . 119.3 ?
N1 C12 H12 . . 119.3 ?
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
O1 N1 . 1.2201(17) ?
O2 N1 . 1.2335(16) ?
N1 C12 . 1.4417(19) ?
C1 C2 . 1.3841(19) ?
C1 C9 . 1.4381(19) ?
C1 C11 . 1.4613(19) ?
C2 C3 . 1.398(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.370(2) ?
C3 H3 . 0.95 ?
C4 C10 . 1.415(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.366(2) ?
C5 C10 . 1.422(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.411(2) ?
C6 H6 . 0.95 ?
C7 C8 . 1.371(2) ?
C7 H7 . 0.95 ?
C8 C9 . 1.4220(19) ?
C8 H8 . 0.95 ?
C9 C10 . 1.4265(19) ?
C11 C12 . 1.316(2) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2 O2 5_666 0.95 2.58 3.3919(19) 144
C7 H7 O2 7_566 0.95 2.52 3.4261(19) 159
C12 H12 O2 5_666 0.95 2.57 3.464(2) 158
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 C1 C2 C3 . . . . -1.2(2) ?
C11 C1 C2 C3 . . . . 178.42(13) ?
C1 C2 C3 C4 . . . . -0.1(2) ?
C2 C3 C4 C10 . . . . 0.6(2) ?
C10 C5 C6 C7 . . . . 0.0(2) ?
C5 C6 C7 C8 . . . . -0.7(2) ?
C6 C7 C8 C9 . . . . 0.5(2) ?
C7 C8 C9 C10 . . . . 0.2(2) ?
C7 C8 C9 C1 . . . . -179.20(14) ?
C2 C1 C9 C8 . . . . -178.57(13) ?
C11 C1 C9 C8 . . . . 1.8(2) ?
C2 C1 C9 C10 . . . . 2.03(19) ?
C11 C1 C9 C10 . . . . -177.61(12) ?
C3 C4 C10 C5 . . . . -179.96(14) ?
C3 C4 C10 C9 . . . . 0.2(2) ?
C6 C5 C10 C4 . . . . -179.12(14) ?
C6 C5 C10 C9 . . . . 0.7(2) ?
C8 C9 C10 C4 . . . . 179.02(12) ?
C1 C9 C10 C4 . . . . -1.6(2) ?
C8 C9 C10 C5 . . . . -0.79(19) ?
C1 C9 C10 C5 . . . . 178.64(13) ?
C2 C1 C11 C12 . . . . -7.4(2) ?
C9 C1 C11 C12 . . . . 172.20(15) ?
C1 C11 C12 N1 . . . . -178.90(14) ?
O1 N1 C12 C11 . . . . -6.4(2) ?
O2 N1 C12 C11 . . . . 173.19(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4529552
