#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/12/2231257.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_2231257
loop_
_publ_author_name
'Kitamura, Mitsuru'
'Sakata, Rie'
'Matsumoto, Taisuke'
_publ_section_title
;
 1-Diazonaphthalen-2(1H)-one
;
_journal_coeditor_code           PV2420
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1951
_journal_paper_doi               10.1107/S1600536811026377
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H6 N2 O'
_chemical_formula_moiety         'C10 H6 N2 O'
_chemical_formula_sum            'C10 H6 N2 O'
_chemical_formula_weight         170.17
_chemical_name_systematic
;
1-Diazonaphthalen-2(1H)-one
;
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   11.900(2)
_cell_length_b                   9.1978(15)
_cell_length_c                   14.521(3)
_cell_measurement_reflns_used    17442
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.0
_cell_volume                     1589.4(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction
'CrystalStructure (Rigaku Americas and Rigaku, 2007)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material
;
CrystalStructure (Rigaku Americas and Rigaku, 2007) and publCIF (Westrip,
2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 5.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18038
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  0.731
_exptl_absorpt_correction_T_min  0.566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1456
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0661P)²+0.5878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                1359
_reflns_number_total             1456
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            pv2420.cif
_cod_data_source_block           I
_cod_database_code               2231257
_cod_database_fobs_code          2231257
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,1/2-Y,1/2+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,1/2+Y,1/2-Z
8 1/2+X,+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_symmetry_multiplicity
O O(1) 0.41204(11) 1.07612(13) 0.22608(7) 0.0476(3) Uani d . 1.00 1
N N(1) 0.55271(11) 0.89513(13) 0.31064(8) 0.0327(3) Uani d . 1.00 1
N N(2) 0.63438(13) 0.87983(16) 0.27341(9) 0.0441(3) Uani d . 1.00 1
C C(1) 0.45523(13) 0.92398(16) 0.35238(10) 0.0336(3) Uani d . 1.00 1
C C(2) 0.38659(14) 1.02931(17) 0.30396(11) 0.0390(4) Uani d . 1.00 1
C C(3) 0.28687(14) 1.07339(17) 0.35513(11) 0.0406(4) Uani d . 1.00 1
C C(4) 0.26340(13) 1.01769(18) 0.43965(12) 0.0419(4) Uani d . 1.00 1
C C(5) 0.33263(12) 0.91102(16) 0.48560(10) 0.0344(3) Uani d . 1.00 1
C C(6) 0.30613(13) 0.85591(18) 0.57389(11) 0.0389(4) Uani d . 1.00 1
C C(7) 0.37387(14) 0.75293(19) 0.61482(11) 0.0395(4) Uani d . 1.00 1
C C(8) 0.46903(13) 0.70173(19) 0.56895(11) 0.0388(4) Uani d . 1.00 1
C C(9) 0.49762(13) 0.75479(17) 0.48334(10) 0.0343(3) Uani d . 1.00 1
C C(10) 0.43117(12) 0.85986(16) 0.44128(10) 0.0310(3) Uani d . 1.00 1
H H(1) 0.2371 1.1427 0.3288 0.049 Uiso c R 1.00 1
H H(2) 0.1977 1.0508 0.4703 0.050 Uiso c R 1.00 1
H H(3) 0.2412 0.8901 0.6052 0.047 Uiso c R 1.00 1
H H(4) 0.3558 0.7168 0.6743 0.047 Uiso c R 1.00 1
H H(5) 0.5146 0.6295 0.5971 0.047 Uiso c R 1.00 1
H H(6) 0.5629 0.7195 0.4530 0.041 Uiso c R 1.00 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, 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
N(2) N(1) C(1) 175.50(14) .
N(1) C(1) C(2) 113.72(13) .
N(1) C(1) C(10) 119.70(13) .
C(2) C(1) C(10) 126.40(13) .
O(1) C(2) C(1) 122.26(14) .
O(1) C(2) C(3) 124.32(14) .
C(1) C(2) C(3) 113.42(13) .
C(2) C(3) C(4) 121.52(14) .
C(3) C(4) C(5) 123.78(14) .
C(4) C(5) C(6) 122.35(13) .
C(4) C(5) C(10) 119.17(13) .
C(6) C(5) C(10) 118.48(13) .
C(5) C(6) C(7) 120.45(14) .
C(6) C(7) C(8) 120.04(14) .
C(7) C(8) C(9) 120.75(15) .
C(8) C(9) C(10) 120.14(14) .
C(1) C(10) C(5) 115.66(12) .
C(1) C(10) C(9) 124.23(13) .
C(5) C(10) C(9) 120.11(13) .
C(2) C(3) H(1) 119.2 no
C(4) C(3) H(1) 119.2 no
C(3) C(4) H(2) 118.1 no
C(5) C(4) H(2) 118.1 no
C(5) C(6) H(3) 119.8 no
C(7) C(6) H(3) 119.8 no
C(6) C(7) H(4) 120.0 no
C(8) C(7) H(4) 120.0 no
C(7) C(8) H(5) 119.6 no
C(9) C(8) H(5) 119.6 no
C(8) C(9) H(6) 119.9 no
C(10) C(9) H(6) 119.9 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(2) 1.2474(19) .
N(1) N(2) 1.1210(19) .
N(1) C(1) 1.3355(19) .
C(1) C(2) 1.449(2) .
C(1) C(10) 1.448(2) .
C(2) C(3) 1.458(2) .
C(3) C(4) 1.359(2) .
C(4) C(5) 1.444(2) .
C(5) C(6) 1.414(2) .
C(5) C(10) 1.418(2) .
C(6) C(7) 1.378(2) .
C(7) C(8) 1.396(2) .
C(8) C(9) 1.378(2) .
C(9) C(10) 1.390(2) .
C(3) H(1) 0.950 no
C(4) H(2) 0.950 no
C(6) H(3) 0.950 no
C(7) H(4) 0.950 no
C(8) H(5) 0.950 no
C(9) H(6) 0.950 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H3 O1 1_555 1_555 4_575 0.95 2.55 3.466(2) 162 yes
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
N(2) N(1) C(1) C(2) 29.7(19)
N(2) N(1) C(1) C(10) -145.8(18)
N(1) C(1) C(2) O(1) 7.0(2)
N(1) C(1) C(2) C(3) -173.04(13)
N(1) C(1) C(10) C(5) 172.20(13)
N(1) C(1) C(10) C(9) -7.8(2)
C(2) C(1) C(10) C(5) -2.6(2)
C(2) C(1) C(10) C(9) 177.38(15)
C(10) C(1) C(2) O(1) -177.92(14)
C(10) C(1) C(2) C(3) 2.1(2)
O(1) C(2) C(3) C(4) 179.61(15)
C(1) C(2) C(3) C(4) -0.4(2)
C(2) C(3) C(4) C(5) -0.6(2)
C(3) C(4) C(5) C(6) 179.60(15)
C(3) C(4) C(5) C(10) 0.0(2)
C(4) C(5) C(6) C(7) 179.26(15)
C(4) C(5) C(10) C(1) 1.5(2)
C(4) C(5) C(10) C(9) -178.53(14)
C(6) C(5) C(10) C(1) -178.15(13)
C(6) C(5) C(10) C(9) 1.8(2)
C(10) C(5) C(6) C(7) -1.1(2)
C(5) C(6) C(7) C(8) -0.3(2)
C(6) C(7) C(8) C(9) 1.1(2)
C(7) C(8) C(9) C(10) -0.4(2)
C(8) C(9) C(10) C(1) 178.89(14)
C(8) C(9) C(10) C(5) -1.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 149716
