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#$Date: 2022-11-24 10:16:25 +0200 (Thu, 24 Nov 2022) $
#$Revision: 279529 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106231.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106231
loop_
_publ_author_name
'Yun-Chen, Zhang'
'Hong-Mei, Guo'
'Peng-Fei, Li'
'Qing-Yun, Liu'
'Xi-Shi, Tai'
_publ_section_title
;
 The crystal structure of phthalazin-1(2H)-one, C8H6N2O1
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              605
_journal_page_last               606
_journal_paper_doi               10.1515/ncrs-2017-0363
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C8 H6 N2 O'
_chemical_formula_weight         146.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 110.54(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.6277(17)
_cell_length_b                   13.134(3)
_cell_length_c                   13.062(5)
_cell_measurement_reflns_used    3138
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4533
_cell_measurement_theta_min      2.3432
_cell_volume                     1386.0(7)
_computing_molecular_graphics    DIAMOND
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  bruker-CCD
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13032
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.102
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9589
_exptl_absorpt_correction_T_min  0.9456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0959P)²+0.0982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1581
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2245
_reflns_number_total             3138
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0363_suppl.cif
_cod_data_source_block           ww
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106231
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.84243(13) 0.04037(8) -0.04692(8) 0.0620(3) Uani 1 1 d . . . . .
O2 O -0.17390(13) -0.27718(9) 0.34484(8) 0.0677(4) Uani 1 1 d . . . . .
N1 N -0.66639(14) 0.03685(9) 0.12816(9) 0.0517(3) Uani 1 1 d . . . . .
H1 H -0.7129 0.0915 0.1395 0.062 Uiso 1 1 d R U . . .
N2 N -0.53958(16) -0.00063(10) 0.21561(10) 0.0576(3) Uani 1 1 d . . . . .
N3 N -0.01109(15) -0.27420(10) 0.52333(10) 0.0559(3) Uani 1 1 d . . . . .
H3A H -0.0634 -0.3272 0.5324 0.067 Uiso 1 1 d R U . . .
N4 N 0.11120(18) -0.23882(10) 0.61446(10) 0.0637(4) Uani 1 1 d . . . . .
C1 C -0.69882(18) -0.14301(10) -0.09423(11) 0.0498(3) Uani 1 1 d . . . . .
H1A H -0.7878 -0.1172 -0.1518 0.060 Uiso 1 1 calc R U . . .
C2 C -0.6176(2) -0.22821(11) -0.10878(13) 0.0600(4) Uani 1 1 d . . . . .
H2 H -0.6521 -0.2610 -0.1762 0.072 Uiso 1 1 calc R U . . .
C3 C -0.4829(2) -0.26585(12) -0.02245(14) 0.0660(5) Uani 1 1 d . . . . .
H3 H -0.4263 -0.3225 -0.0338 0.079 Uiso 1 1 calc R U . . .
C4 C -0.4320(2) -0.22085(11) 0.07906(13) 0.0595(4) Uani 1 1 d . . . . .
H4 H -0.3433 -0.2476 0.1362 0.071 Uiso 1 1 calc R U . . .
C5 C -0.51541(16) -0.13426(10) 0.09538(11) 0.0457(3) Uani 1 1 d . . . . .
C6 C -0.46988(18) -0.08258(11) 0.19859(11) 0.0542(4) Uani 1 1 d . . . . .
H6 H -0.3843 -0.1101 0.2572 0.065 Uiso 1 1 calc R U . . .
C7 C -0.72784(16) -0.00225(10) 0.02505(11) 0.0452(3) Uani 1 1 d . . . . .
C8 C -0.64710(16) -0.09490(9) 0.00785(10) 0.0418(3) Uani 1 1 d . . . . .
C9 C 0.2485(2) -0.02416(13) 0.48736(14) 0.0676(5) Uani 1 1 d . . . . .
H9 H 0.3325 0.0019 0.5478 0.081 Uiso 1 1 calc R U . . .
C10 C 0.2151(2) 0.01896(13) 0.38601(14) 0.0725(5) Uani 1 1 d . . . . .
H10 H 0.2777 0.0741 0.3782 0.087 Uiso 1 1 calc R U . . .
C11 C 0.0889(2) -0.01885(12) 0.29494(13) 0.0617(4) Uani 1 1 d . . . . .
H11 H 0.0667 0.0120 0.2272 0.074 Uiso 1 1 calc R U . . .
C12 C -0.00259(17) -0.10091(11) 0.30436(11) 0.0511(4) Uani 1 1 d . . . . .
H12 H -0.0857 -0.1266 0.2431 0.061 Uiso 1 1 calc R U . . .
C13 C 0.02968(15) -0.14593(10) 0.40676(10) 0.0436(3) Uani 1 1 d . . . . .
C14 C -0.06045(17) -0.23598(11) 0.42009(11) 0.0483(3) Uani 1 1 d . . . . .
C15 C 0.1887(2) -0.15904(12) 0.60113(12) 0.0619(4) Uani 1 1 d . . . . .
H15 H 0.2723 -0.1331 0.6619 0.074 Uiso 1 1 calc R U . . .
C16 C 0.15498(18) -0.10753(10) 0.49880(11) 0.0499(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C7 N1 N2 127.59(12) . .
C7 N1 H1 116.2 . .
N2 N1 H1 116.2 . .
C6 N2 N1 116.20(12) . .
C14 N3 N4 128.04(12) . .
C14 N3 H3A 116.0 . .
N4 N3 H3A 116.0 . .
C15 N4 N3 115.99(12) . .
C2 C1 C8 119.59(13) . .
C2 C1 H1A 120.2 . .
C8 C1 H1A 120.2 . .
C1 C2 C3 119.96(14) . .
C1 C2 H2 120.0 . .
C3 C2 H2 120.0 . .
C4 C3 C2 121.36(14) . .
C4 C3 H3 119.3 . .
C2 C3 H3 119.3 . .
C3 C4 C5 119.21(14) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
C8 C5 C4 119.28(13) . .
C8 C5 C6 117.99(12) . .
C4 C5 C6 122.72(13) . .
N2 C6 C5 124.47(13) . .
N2 C6 H6 117.8 . .
C5 C6 H6 117.8 . .
O1 C7 N1 120.78(13) . .
O1 C7 C8 124.03(12) . .
N1 C7 C8 115.18(12) . .
C5 C8 C1 120.54(13) . .
C5 C8 C7 118.54(12) . .
C1 C8 C7 120.91(12) . .
C10 C9 C16 119.47(15) . .
C10 C9 H9 120.3 . .
C16 C9 H9 120.3 . .
C9 C10 C11 120.83(14) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C12 C11 C10 120.51(14) . .
C12 C11 H11 119.7 . .
C10 C11 H11 119.7 . .
C11 C12 C13 119.48(13) . .
C11 C12 H12 120.3 . .
C13 C12 H12 120.3 . .
C12 C13 C16 120.28(12) . .
C12 C13 C14 121.43(12) . .
C16 C13 C14 118.24(12) . .
O2 C14 N3 120.65(13) . .
O2 C14 C13 124.32(12) . .
N3 C14 C13 115.03(12) . .
N4 C15 C16 124.39(14) . .
N4 C15 H15 117.8 . .
C16 C15 H15 117.8 . .
C13 C16 C9 119.42(13) . .
C13 C16 C15 118.30(13) . .
C9 C16 C15 122.20(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.2338(16) .
O2 C14 1.2418(16) .
N1 C7 1.3630(18) .
N1 N2 1.3664(17) .
N1 H1 0.8600 .
N2 C6 1.2897(18) .
N3 C14 1.3597(18) .
N3 N4 1.3656(18) .
N3 H3A 0.8600 .
N4 C15 1.2875(19) .
C1 C2 1.3685(19) .
C1 C8 1.3995(19) .
C1 H1A 0.9300 .
C2 C3 1.395(2) .
C2 H2 0.9300 .
C3 C4 1.375(2) .
C3 H3 0.9300 .
C4 C5 1.4015(19) .
C4 H4 0.9300 .
C5 C8 1.3977(19) .
C5 C6 1.4357(19) .
C6 H6 0.9300 .
C7 C8 1.4581(18) .
C9 C10 1.374(2) .
C9 C16 1.399(2) .
C9 H9 0.9300 .
C10 C11 1.392(2) .
C10 H10 0.9300 .
C11 C12 1.367(2) .
C11 H11 0.9300 .
C12 C13 1.3981(19) .
C12 H12 0.9300 .
C13 C16 1.3987(19) .
C13 C14 1.4592(18) .
C15 C16 1.434(2) .
C15 H15 0.9300 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C7 N1 N2 C6 0.0(2) . . . .
C14 N3 N4 C15 0.4(3) . . . .
C8 C1 C2 C3 -0.7(2) . . . .
C1 C2 C3 C4 2.0(3) . . . .
C2 C3 C4 C5 -1.2(3) . . . .
C3 C4 C5 C8 -0.7(2) . . . .
C3 C4 C5 C6 -179.80(15) . . . .
N1 N2 C6 C5 0.9(2) . . . .
C8 C5 C6 N2 -1.8(2) . . . .
C4 C5 C6 N2 177.27(15) . . . .
N2 N1 C7 O1 -179.18(13) . . . .
N2 N1 C7 C8 0.0(2) . . . .
C4 C5 C8 C1 2.0(2) . . . .
C6 C5 C8 C1 -178.93(12) . . . .
C4 C5 C8 C7 -177.39(12) . . . .
C6 C5 C8 C7 1.71(19) . . . .
C2 C1 C8 C5 -1.2(2) . . . .
C2 C1 C8 C7 178.12(13) . . . .
O1 C7 C8 C5 178.26(13) . . . .
N1 C7 C8 C5 -0.91(18) . . . .
O1 C7 C8 C1 -1.1(2) . . . .
N1 C7 C8 C1 179.73(12) . . . .
C16 C9 C10 C11 0.5(3) . . . .
C9 C10 C11 C12 -1.1(3) . . . .
C10 C11 C12 C13 1.0(3) . . . .
C11 C12 C13 C16 -0.2(2) . . . .
C11 C12 C13 C14 -177.63(13) . . . .
N4 N3 C14 O2 179.57(14) . . . .
N4 N3 C14 C13 -0.1(2) . . . .
C12 C13 C14 O2 -2.5(2) . . . .
C16 C13 C14 O2 -179.96(14) . . . .
C12 C13 C14 N3 177.20(13) . . . .
C16 C13 C14 N3 -0.27(19) . . . .
N3 N4 C15 C16 -0.4(3) . . . .
C12 C13 C16 C9 -0.4(2) . . . .
C14 C13 C16 C9 177.05(14) . . . .
C12 C13 C16 C15 -177.16(13) . . . .
C14 C13 C16 C15 0.3(2) . . . .
C10 C9 C16 C13 0.3(3) . . . .
C10 C9 C16 C15 176.89(17) . . . .
N4 C15 C16 C13 0.0(3) . . . .
N4 C15 C16 C9 -176.63(16) . . . .
