#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/42/2214260.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_2214260
loop_
_publ_author_name
'Büyükgüngör, Orhan'
'Odabaşoǧlu, Mustafa'
'Narayana, B.'
'Vijeshi, A. M. '
'Yathirajan, H. S.'
_publ_section_title
;
 Phthalazin-1(2H)-one
;
_journal_coeditor_code           HK2270
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3198
_journal_page_last               o3198
_journal_paper_doi               10.1107/S1600536807027523
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H6 N2 O'
_chemical_formula_moiety         'C8 H6 N2 O'
_chemical_formula_sum            'C8 H6 N2 O'
_chemical_formula_weight         146.15
_chemical_name_systematic
;
Phthalazin-1(2H)-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           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90.534(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.0321(3)
_cell_length_b                   12.3412(13)
_cell_length_c                   13.7513(10)
_cell_measurement_reflns_used    9171
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.96
_cell_volume                     684.25(10)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9171
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.96
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9785
_exptl_absorpt_correction_T_min  0.9440
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0379
_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)+(0.0487P)²+0.0889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                1064
_reflns_number_total             1324
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2270.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214260
_cod_database_fobs_code          2214260
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_occupancy
C C1 0.8204(4) 0.04381(11) 0.86523(10) 0.0480(4) Uani d 1
C C2 0.7038(3) 0.08027(11) 0.77005(9) 0.0440(3) Uani d 1
C C3 0.5213(4) 0.01188(13) 0.70937(11) 0.0523(4) Uani d 1
C C4 0.4186(4) 0.04883(16) 0.62008(12) 0.0623(4) Uani d 1
C C5 0.4969(5) 0.15293(16) 0.58975(12) 0.0672(5) Uani d 1
C C6 0.6760(4) 0.22069(15) 0.64822(12) 0.0607(4) Uani d 1
C C7 0.7822(4) 0.18524(12) 0.74036(10) 0.0482(4) Uani d 1
C C8 0.9696(4) 0.25138(12) 0.80633(12) 0.0560(4) Uani d 1
N N1 0.9897(3) 0.11846(10) 0.91799(9) 0.0539(3) Uani d 1
N N2 1.0698(3) 0.22166(10) 0.89115(10) 0.0586(4) Uani d 1
O O1 0.7743(3) -0.04865(8) 0.89695(8) 0.0663(4) Uani d 1
H H1 1.074(5) 0.0989(15) 0.9782(15) 0.078(6) Uiso d 1
H H3 0.470(4) -0.0610(15) 0.7317(13) 0.063(5) Uiso d 1
H H4 0.291(5) 0.0011(15) 0.5808(14) 0.076(5) Uiso d 1
H H5 0.421(5) 0.1757(15) 0.5269(15) 0.079(5) Uiso d 1
H H6 0.728(4) 0.2924(14) 0.6304(12) 0.069(5) Uiso d 1
H H8 1.030(4) 0.3249(15) 0.7875(12) 0.063(5) Uiso d 1
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
C1 0.0569(8) 0.0442(7) 0.0428(7) 0.0024(6) -0.0040(6) 0.0005(6)
C2 0.0469(7) 0.0472(7) 0.0380(7) 0.0089(6) 0.0003(5) 0.0005(5)
C3 0.0547(9) 0.0567(9) 0.0455(8) 0.0057(7) -0.0029(6) -0.0031(7)
C4 0.0610(10) 0.0817(12) 0.0439(8) 0.0118(8) -0.0075(7) -0.0084(8)
C5 0.0710(11) 0.0895(13) 0.0410(8) 0.0258(9) -0.0023(7) 0.0093(8)
C6 0.0689(10) 0.0630(10) 0.0503(9) 0.0176(8) 0.0050(7) 0.0148(7)
C7 0.0502(8) 0.0481(8) 0.0463(7) 0.0115(6) 0.0055(6) 0.0046(6)
C8 0.0619(9) 0.0430(8) 0.0632(9) 0.0020(7) 0.0020(7) 0.0045(7)
N1 0.0704(9) 0.0481(7) 0.0430(7) -0.0025(6) -0.0099(6) 0.0015(5)
N2 0.0683(9) 0.0470(7) 0.0604(8) -0.0025(6) -0.0067(6) -0.0017(6)
O1 0.0955(9) 0.0494(6) 0.0536(6) -0.0116(6) -0.0212(6) 0.0114(5)
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
O1 C1 N1 121.06(13)
O1 C1 C2 123.59(13)
N1 C1 C2 115.34(12)
C3 C2 C7 120.49(13)
C3 C2 C1 121.01(13)
C7 C2 C1 118.50(13)
C4 C3 C2 119.27(15)
C4 C3 H3 121.8(10)
C2 C3 H3 118.9(10)
C3 C4 C5 120.64(16)
C3 C4 H4 117.5(12)
C5 C4 H4 121.8(11)
C6 C5 C4 120.76(15)
C6 C5 H5 121.1(12)
C4 C5 H5 118.1(12)
C5 C6 C7 119.80(16)
C5 C6 H6 122.7(11)
C7 C6 H6 117.5(11)
C2 C7 C6 119.04(15)
C2 C7 C8 117.64(13)
C6 C7 C8 123.32(15)
N2 C8 C7 124.93(14)
N2 C8 H8 115.4(10)
C7 C8 H8 119.7(10)
C1 N1 N2 127.55(13)
C1 N1 H1 118.8(12)
N2 N1 H1 113.6(12)
C8 N2 N1 116.01(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2363(17)
C1 N1 1.3533(18)
C1 C2 1.4580(18)
C2 C3 1.392(2)
C2 C7 1.395(2)
C3 C4 1.370(2)
C3 H3 0.973(18)
C4 C5 1.388(3)
C4 H4 0.947(19)
C5 C6 1.363(3)
C5 H5 0.96(2)
C6 C7 1.404(2)
C6 H6 0.942(17)
C7 C8 1.431(2)
C8 N2 1.284(2)
C8 H8 0.975(18)
N1 N2 1.3656(18)
N1 H1 0.92(2)
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
N1 H1 O1 3_757 0.92(2) 1.92(2) 2.8423(16) 175.5(17)
C5 H5 N2 4_465 0.96(2) 2.65(2) 3.568(2) 160.0(15)
C6 H6 O1 2_656 0.942(17) 2.841(17) 3.4298(19) 121.6(12)
C6 H6 O1 2_756 0.942(17) 2.835(17) 3.664(2) 147.5(13)
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
O1 C1 C2 C3 1.9(2)
N1 C1 C2 C3 -178.83(14)
O1 C1 C2 C7 -177.44(14)
N1 C1 C2 C7 1.88(19)
C7 C2 C3 C4 -0.2(2)
C1 C2 C3 C4 -179.43(13)
C2 C3 C4 C5 0.5(2)
C3 C4 C5 C6 -0.3(3)
C4 C5 C6 C7 -0.2(2)
C3 C2 C7 C6 -0.3(2)
C1 C2 C7 C6 178.96(13)
C3 C2 C7 C8 179.84(14)
C1 C2 C7 C8 -0.86(19)
C5 C6 C7 C2 0.5(2)
C5 C6 C7 C8 -179.68(15)
C2 C7 C8 N2 -0.4(2)
C6 C7 C8 N2 179.79(15)
O1 C1 N1 N2 177.40(15)
C2 C1 N1 N2 -1.9(2)
C7 C8 N2 N1 0.5(2)
C1 N1 N2 C8 0.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8088
