#------------------------------------------------------------------------------
#$Date: 2022-04-01 05:24:18 +0300 (Fri, 01 Apr 2022) $
#$Revision: 274192 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/67/1566728.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_1566728
loop_
_publ_author_name
'Song, Jingjing'
'Jiang, Xinyu'
'Wang, Ziyi'
'Pei, Jingyao'
'Li, Hongsen'
_publ_section_title
;
 4-Chloro-5-(dimethylamino)-2-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]pyridazin-3(2H)-one
;
_journal_coeditor_code           VM4052
_journal_issue                   3
_journal_name_full               IUCrData
_journal_page_first              x220342
_journal_paper_doi               10.1107/S241431462200342X
_journal_volume                  7
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C15 H14 Cl N5 O2'
_chemical_formula_moiety         'C15 H14 Cl N5 O2'
_chemical_formula_sum            'C15 H14 Cl N5 O2'
_chemical_formula_weight         331.76
_chemical_name_systematic
4-Chloro-5-(dimethylamino)-2-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]pyridazin-3(2H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 98.128(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1533(16)
_cell_length_b                   11.936(3)
_cell_length_c                   9.004(2)
_cell_measurement_reflns_used    2107
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.647
_cell_measurement_theta_min      5.704
_cell_volume                     761.1(3)
_computing_cell_refinement
;
SMART (Bruker, 2002)
;
_computing_data_collection
;
SMART (Bruker, 2002)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4542
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.285
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2002)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.303
_refine_ls_abs_structure_details
;
Flack x determined using 1139 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       0.029(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2915
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0418
_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)+(0.0624P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                2673
_reflns_number_total             2915
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm4052sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1566728
_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   0.943
_shelx_estimated_absorpt_t_max   0.968
_shelxl_version_number           .2013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.85200(15) 0.73449(8) 0.58094(11) 0.0698(3) Uani d 1 . .
N N1 0.3672(4) 1.1087(2) 0.1248(3) 0.0522(7) Uani d 1 . .
N N2 0.5386(4) 1.0502(2) 0.1672(3) 0.0525(7) Uani d 1 . .
N N3 0.8278(4) 0.8804(2) 0.1888(3) 0.0450(6) Uani d 1 . .
N N4 0.9890(4) 0.9391(2) 0.1928(3) 0.0503(7) Uani d 1 . .
N N5 1.2442(4) 0.8512(2) 0.5493(3) 0.0501(7) Uani d 1 . .
O O1 0.3908(3) 0.97490(18) -0.0393(2) 0.0446(5) Uani d 1 . .
O O2 0.6230(4) 0.7702(2) 0.2898(3) 0.0695(8) Uani d 1 . .
C C1 0.0415(5) 1.0303(3) -0.2139(4) 0.0530(8) Uani d 1 . .
H H1 0.1196 0.9776 -0.2501 0.064 Uiso calc 1 . .
C C2 -0.1339(5) 1.0519(4) -0.2928(4) 0.0629(10) Uani d 1 . .
H H2 -0.1736 1.0139 -0.3818 0.075 Uiso calc 1 . .
C C3 -0.2509(5) 1.1296(3) -0.2406(5) 0.0619(10) Uani d 1 . .
H H3 -0.3693 1.1446 -0.2939 0.074 Uiso calc 1 . .
C C4 -0.1906(6) 1.1849(3) -0.1086(5) 0.0605(9) Uani d 1 . .
H H4 -0.2695 1.2372 -0.0726 0.073 Uiso calc 1 . .
C C5 -0.0155(5) 1.1641(3) -0.0288(4) 0.0526(8) Uani d 1 . .
H H5 0.0237 1.2023 0.0601 0.063 Uiso calc 1 . .
C C6 0.1024(4) 1.0857(3) -0.0819(3) 0.0425(7) Uani d 1 . .
C C7 0.2862(4) 1.0612(2) 0.0054(3) 0.0406(7) Uani d 1 . .
C C8 0.5443(4) 0.9750(3) 0.0679(3) 0.0422(7) Uani d 1 . .
C C9 0.6961(5) 0.8919(3) 0.0516(4) 0.0502(8) Uani d 1 . .
H H9A 0.6391 0.8196 0.0245 0.060 Uiso calc 1 . .
H H9B 0.7642 0.9154 -0.0289 0.060 Uiso calc 1 . .
C C10 0.7789(4) 0.8150(3) 0.3034(4) 0.0453(7) Uani d 1 . .
C C11 0.9230(5) 0.8076(3) 0.4331(3) 0.0449(7) Uani d 1 . .
C C12 1.0946(4) 0.8589(3) 0.4373(3) 0.0396(6) Uani d 1 . .
C C13 1.1132(5) 0.9282(3) 0.3105(4) 0.0473(8) Uani d 1 . .
H H13 1.2245 0.9690 0.3132 0.057 Uiso calc 1 . .
C C14 1.2910(6) 0.7498(4) 0.6345(4) 0.0692(11) Uani d 1 . .
H H14A 1.2811 0.7631 0.7382 0.104 Uiso calc 1 . .
H H14B 1.4178 0.7277 0.6249 0.104 Uiso calc 1 . .
H H14C 1.2052 0.6912 0.5968 0.104 Uiso calc 1 . .
C C15 1.4001(5) 0.9309(4) 0.5556(4) 0.0636(10) Uani d 1 . .
H H15A 1.4852 0.9073 0.4882 0.095 Uiso calc 1 . .
H H15B 1.4664 0.9339 0.6559 0.095 Uiso calc 1 . .
H H15C 1.3513 1.0038 0.5266 0.095 Uiso calc 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'
Cl Cl 0.1484 0.1585 '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
C7 N1 N2 . . 106.3(3) ?
C8 N2 N1 . . 105.7(2) ?
N4 N3 C10 . . 125.6(3) ?
N4 N3 C9 . . 115.2(3) ?
C10 N3 C9 . . 119.2(3) ?
C13 N4 N3 . . 117.3(3) ?
C12 N5 C14 . . 123.1(3) ?
C12 N5 C15 . . 119.9(3) ?
C14 N5 C15 . . 114.0(3) ?
C8 O1 C7 . . 102.2(2) ?
C6 C1 C2 . . 120.7(3) ?
C6 C1 H1 . . 119.7 ?
C2 C1 H1 . . 119.7 ?
C3 C2 C1 . . 120.3(4) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C4 C3 C2 . . 119.2(4) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C5 . . 121.1(3) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C4 C5 C6 . . 119.6(4) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C1 C6 C5 . . 119.2(3) ?
C1 C6 C7 . . 121.3(3) ?
C5 C6 C7 . . 119.5(3) ?
N1 C7 O1 . . 112.3(3) ?
N1 C7 C6 . . 129.0(3) ?
O1 C7 C6 . . 118.7(3) ?
N2 C8 O1 . . 113.4(3) ?
N2 C8 C9 . . 129.4(3) ?
O1 C8 C9 . . 117.2(3) ?
N3 C9 C8 . . 111.9(3) ?
N3 C9 H9A . . 109.2 ?
C8 C9 H9A . . 109.2 ?
N3 C9 H9B . . 109.2 ?
C8 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
O2 C10 N3 . . 119.7(3) ?
O2 C10 C11 . . 126.0(3) ?
N3 C10 C11 . . 114.3(3) ?
C12 C11 C10 . . 122.0(3) ?
C12 C11 Cl1 . . 124.4(2) ?
C10 C11 Cl1 . . 113.5(2) ?
N5 C12 C11 . . 126.6(3) ?
N5 C12 C13 . . 118.4(3) ?
C11 C12 C13 . . 114.9(3) ?
N4 C13 C12 . . 125.6(3) ?
N4 C13 H13 . . 117.2 ?
C12 C13 H13 . . 117.2 ?
N5 C14 H14A . . 109.5 ?
N5 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N5 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N5 C15 H15A . . 109.5 ?
N5 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
N5 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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
Cl1 C11 . 1.727(3) ?
N1 C7 . 1.279(4) ?
N1 N2 . 1.415(4) ?
N2 C8 . 1.272(4) ?
N3 N4 . 1.345(4) ?
N3 C10 . 1.378(4) ?
N3 C9 . 1.450(4) ?
N4 C13 . 1.290(4) ?
N5 C12 . 1.366(4) ?
N5 C14 . 1.447(5) ?
N5 C15 . 1.461(5) ?
O1 C8 . 1.355(3) ?
O1 C7 . 1.367(4) ?
O2 C10 . 1.227(4) ?
C1 C6 . 1.376(5) ?
C1 C2 . 1.376(5) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.376(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.374(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.376(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.389(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.462(4) ?
C8 C9 . 1.494(5) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.447(4) ?
C11 C12 . 1.367(5) ?
C12 C13 . 1.432(4) ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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
C14 H14C Cl1 . 0.96 2.56 3.114(4) 117
C1 H1 O1 . 0.93 2.52 2.836(4) 100
C3 H3 O2 2_555 0.93 2.36 3.125(5) 140
C1 H1 N5 1_454 0.93 2.61 3.477(5) 156
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
C7 N1 N2 C8 . . . . 1.0(4) ?
C10 N3 N4 C13 . . . . 4.2(5) ?
C9 N3 N4 C13 . . . . -177.5(3) ?
C6 C1 C2 C3 . . . . 0.0(6) ?
C1 C2 C3 C4 . . . . -0.2(6) ?
C2 C3 C4 C5 . . . . 0.3(6) ?
C3 C4 C5 C6 . . . . -0.2(5) ?
C2 C1 C6 C5 . . . . 0.1(5) ?
C2 C1 C6 C7 . . . . 178.2(3) ?
C4 C5 C6 C1 . . . . 0.0(5) ?
C4 C5 C6 C7 . . . . -178.1(3) ?
N2 N1 C7 O1 . . . . -0.9(4) ?
N2 N1 C7 C6 . . . . 177.5(3) ?
C8 O1 C7 N1 . . . . 0.5(3) ?
C8 O1 C7 C6 . . . . -178.1(3) ?
C1 C6 C7 N1 . . . . 176.0(3) ?
C5 C6 C7 N1 . . . . -5.9(5) ?
C1 C6 C7 O1 . . . . -5.7(4) ?
C5 C6 C7 O1 . . . . 172.5(3) ?
N1 N2 C8 O1 . . . . -0.7(4) ?
N1 N2 C8 C9 . . . . 177.1(3) ?
C7 O1 C8 N2 . . . . 0.2(4) ?
C7 O1 C8 C9 . . . . -177.9(3) ?
N4 N3 C9 C8 . . . . -98.6(4) ?
C10 N3 C9 C8 . . . . 79.8(4) ?
N2 C8 C9 N3 . . . . 16.7(5) ?
O1 C8 C9 N3 . . . . -165.6(3) ?
N4 N3 C10 O2 . . . . 175.9(3) ?
C9 N3 C10 O2 . . . . -2.2(4) ?
N4 N3 C10 C11 . . . . -3.3(4) ?
C9 N3 C10 C11 . . . . 178.6(3) ?
O2 C10 C11 C12 . . . . 178.8(3) ?
N3 C10 C11 C12 . . . . -2.0(4) ?
O2 C10 C11 Cl1 . . . . -4.0(4) ?
N3 C10 C11 Cl1 . . . . 175.2(2) ?
C14 N5 C12 C11 . . . . 35.7(5) ?
C15 N5 C12 C11 . . . . -165.2(3) ?
C14 N5 C12 C13 . . . . -145.3(3) ?
C15 N5 C12 C13 . . . . 13.8(5) ?
C10 C11 C12 N5 . . . . -175.4(3) ?
Cl1 C11 C12 N5 . . . . 7.8(5) ?
C10 C11 C12 C13 . . . . 5.6(4) ?
Cl1 C11 C12 C13 . . . . -171.3(2) ?
N3 N4 C13 C12 . . . . 0.1(5) ?
N5 C12 C13 N4 . . . . 176.0(3) ?
C11 C12 C13 N4 . . . . -4.9(5) ?

_cod_database_fobs_code 1566728
