#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/75/2237584.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_2237584
loop_
_publ_author_name
'Rybakov, Victor B.'
'Shishkina, Svitlana V.'
'Ukrainets, Igor V.'
'Gorokhova, Olga V.'
'Andreeva, Xeniya V.'
_publ_section_title
;
 6-Hydroxy-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
;
_journal_coeditor_code           YK2087
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o340
_journal_paper_doi               10.1107/S1600536813003000
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C11 H9 N O2'
_chemical_formula_moiety         'C11 H9 N O2'
_chemical_formula_sum            'C11 H9 N O2'
_chemical_formula_weight         187.19
_chemical_melting_point_gt       577
_chemical_melting_point_lt       579
_chemical_name_systematic
;
6-Hydroxy-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
;
_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
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.386(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9987(3)
_cell_length_b                   7.6297(2)
_cell_length_c                   14.3500(4)
_cell_measurement_reflns_used    2056
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      3.03
_cell_volume                     858.51(5)
_computing_cell_refinement       'CrysAlis CCD (Agilent, 2011)'
_computing_data_collection       'CrysAlis CCD (Agilent, 2011)'
_computing_data_reduction        'CrysAlis RED (Agilent, 2011)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Agilent Xcalibur Sapphire3 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X--ray Source '
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7610
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Agilent, 2011)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.0832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                1806
_reflns_number_total             2501
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            yk2087.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2237584
_cod_database_fobs_code          2237584
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_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 O1 0.20058(12) 0.29009(13) 0.28449(6) 0.0523(3) Uani d . 1 1
O O2 -0.01907(13) 0.82083(12) 0.38558(7) 0.0489(3) Uani d . 1 1
H H2 -0.093(3) 0.819(3) 0.3132(16) 0.101(7) Uiso d . 1 1
N N1 0.26368(13) 0.36896(13) 0.43936(7) 0.0369(2) Uani d . 1 1
C C1 0.25940(14) 0.48889(16) 0.51022(8) 0.0345(3) Uani d . 1 1
C C2 0.35421(15) 0.43260(18) 0.59709(8) 0.0407(3) Uani d . 1 1
C C3 0.36190(17) 0.5414(2) 0.67396(9) 0.0507(4) Uani d . 1 1
H H3 0.4236 0.5086 0.7333 0.061 Uiso calc R 1 1
C C4 0.27589(18) 0.7023(2) 0.66225(10) 0.0519(4) Uani d . 1 1
H H4 0.2836 0.7763 0.7144 0.062 Uiso calc R 1 1
C C5 0.18033(17) 0.75496(18) 0.57616(9) 0.0439(3) Uani d . 1 1
H H5 0.1230 0.8617 0.5709 0.053 Uiso calc R 1 1
C C6 0.17035(15) 0.64553(16) 0.49625(8) 0.0354(3) Uani d . 1 1
C C7 0.07582(15) 0.67526(15) 0.40090(8) 0.0362(3) Uani d . 1 1
C C8 0.08626(15) 0.55614(16) 0.33158(8) 0.0391(3) Uani d . 1 1
H H8 0.0262 0.5785 0.2704 0.047 Uiso calc R 1 1
C C9 0.18435(15) 0.39879(16) 0.34778(8) 0.0379(3) Uani d . 1 1
C C10 0.36451(18) 0.21387(18) 0.47642(10) 0.0479(3) Uani d . 1 1
H H10B 0.4609 0.1991 0.4454 0.057 Uiso calc R 1 1
H H10A 0.2951 0.1087 0.4670 0.057 Uiso calc R 1 1
C C11 0.42503(18) 0.25294(19) 0.58354(10) 0.0487(3) Uani d . 1 1
H H11B 0.3808 0.1665 0.6219 0.058 Uiso calc R 1 1
H H11A 0.5486 0.2530 0.6007 0.058 Uiso calc R 1 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
C7 O2 H2 109.2(11)
C9 N1 C1 121.90(10)
C9 N1 C10 126.97(11)
C1 N1 C10 111.12(10)
N1 C1 C6 123.70(10)
N1 C1 C2 111.62(11)
C6 C1 C2 124.68(11)
C3 C2 C1 117.58(13)
C3 C2 C11 133.96(12)
C1 C2 C11 108.44(11)
C2 C3 C4 119.38(12)
C2 C3 H3 120.3
C4 C3 H3 120.3
C5 C4 C3 122.35(13)
C5 C4 H4 118.8
C3 C4 H4 118.8
C4 C5 C6 119.32(13)
C4 C5 H5 120.3
C6 C5 H5 120.3
C1 C6 C5 116.67(11)
C1 C6 C7 115.50(10)
C5 C6 C7 127.82(12)
O2 C7 C8 123.24(11)
O2 C7 C6 117.37(11)
C8 C7 C6 119.40(11)
C7 C8 C9 123.57(10)
C7 C8 H8 118.2
C9 C8 H8 118.2
O1 C9 N1 119.54(11)
O1 C9 C8 124.72(11)
N1 C9 C8 115.74(11)
N1 C10 C11 104.24(10)
N1 C10 H10B 110.9
C11 C10 H10B 110.9
N1 C10 H10A 110.9
C11 C10 H10A 110.9
H10B C10 H10A 108.9
C2 C11 C10 104.54(10)
C2 C11 H11B 110.8
C10 C11 H11B 110.8
C2 C11 H11A 110.8
C10 C11 H11A 110.8
H11B C11 H11A 108.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.2555(14)
O2 C7 1.3387(15)
O2 H2 1.09(2)
N1 C9 1.3610(15)
N1 C1 1.3733(15)
N1 C10 1.4711(16)
C1 C6 1.3855(17)
C1 C2 1.3930(16)
C2 C3 1.3721(19)
C2 C11 1.5104(19)
C3 C4 1.401(2)
C3 H3 0.9300
C4 C5 1.3780(19)
C4 H4 0.9300
C5 C6 1.4079(18)
C5 H5 0.9300
C6 C7 1.4445(16)
C7 C8 1.3622(17)
C8 C9 1.4279(17)
C8 H8 0.9300
C10 C11 1.547(2)
C10 H10B 0.9700
C10 H10A 0.9700
C11 H11B 0.9700
C11 H11A 0.9700
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
O2 H2 O1 2 1.09(2) 1.51(2) 2.5922(13) 172.0(19)
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
C9 N1 C1 C6 2.51(18)
C10 N1 C1 C6 -178.40(11)
C9 N1 C1 C2 -177.90(11)
C10 N1 C1 C2 1.20(15)
N1 C1 C2 C3 179.39(11)
C6 C1 C2 C3 -1.01(19)
N1 C1 C2 C11 -1.98(14)
C6 C1 C2 C11 177.61(11)
C1 C2 C3 C4 -0.2(2)
C11 C2 C3 C4 -178.33(14)
C2 C3 C4 C5 1.2(2)
C3 C4 C5 C6 -1.2(2)
N1 C1 C6 C5 -179.39(11)
C2 C1 C6 C5 1.07(18)
N1 C1 C6 C7 1.52(17)
C2 C1 C6 C7 -178.02(11)
C4 C5 C6 C1 0.04(18)
C4 C5 C6 C7 179.00(12)
C1 C6 C7 O2 176.62(10)
C5 C6 C7 O2 -2.35(19)
C1 C6 C7 C8 -3.23(17)
C5 C6 C7 C8 177.81(12)
O2 C7 C8 C9 -178.65(11)
C6 C7 C8 C9 1.18(19)
C1 N1 C9 O1 175.65(11)
C10 N1 C9 O1 -3.3(2)
C1 N1 C9 C8 -4.50(17)
C10 N1 C9 C8 176.56(11)
C7 C8 C9 O1 -177.46(12)
C7 C8 C9 N1 2.70(18)
C9 N1 C10 C11 179.12(11)
C1 N1 C10 C11 0.08(15)
C3 C2 C11 C10 -179.78(15)
C1 C2 C11 C10 1.92(14)
N1 C10 C11 C2 -1.19(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10553001
