#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/85/2228562.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_2228562
loop_
_publ_author_name
'Kim, Hyunjee'
'Kim, Tae Ho'
'Kim, Jineun'
'Park, Ki-Min'
_publ_section_title
;
 Diclomezine: 6-(3,5-dichloro-4-methylphenyl)pyridazin-3(2H)-one
;
_journal_coeditor_code           SJ5054
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3257
_journal_paper_doi               10.1107/S1600536810047409
_journal_volume                  66
_journal_year                    2010
_chemical_formula_moiety         'C11 H8 Cl2 N2 O'
_chemical_formula_sum            'C11 H8 Cl2 N2 O'
_chemical_formula_weight         255.09
_chemical_name_systematic
;
6-(3,5-dichloro-4-methylphenyl)pyridazin-3(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                90.00
_cell_angle_beta                 111.557(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.745(4)
_cell_length_b                   13.850(5)
_cell_length_c                   8.481(3)
_cell_measurement_reflns_used    3791
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.94
_cell_volume                     1064.6(7)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10410
_diffrn_reflns_theta_full        28.43
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  0.9546
_exptl_absorpt_correction_T_min  0.8968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0323P)²+0.5573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                2038
_reflns_number_total             2657
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5054.cif
_cod_data_source_block           I
_cod_original_cell_volume        1064.7(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228562
_cod_database_fobs_code          2228562
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.11909(5) 0.35378(4) 0.82090(6) 0.03367(14) Uani d . 1 . .
Cl Cl2 0.15267(6) 0.72198(3) 0.62638(7) 0.03884(15) Uani d . 1 . .
O O1 0.52503(15) 0.37232(9) 0.02888(17) 0.0290(3) Uani d . 1 . .
N N1 0.42007(16) 0.47759(11) 0.15589(18) 0.0240(3) Uani d . 1 . .
H H1 0.4313 0.5229 0.0888 0.029 Uiso calc R 1 . .
N N2 0.35554(16) 0.50487(11) 0.26436(18) 0.0239(3) Uani d . 1 . .
C C1 0.47026(19) 0.38769(13) 0.1379(2) 0.0234(4) Uani d . 1 . .
C C2 0.45389(19) 0.31751(13) 0.2541(2) 0.0258(4) Uani d . 1 . .
H H2 0.4893 0.2536 0.2543 0.031 Uiso calc R 1 . .
C C3 0.38829(19) 0.34224(13) 0.3631(2) 0.0246(4) Uani d . 1 . .
H H3 0.3760 0.2954 0.4387 0.029 Uiso calc R 1 . .
C C4 0.33735(18) 0.43848(12) 0.3652(2) 0.0214(3) Uani d . 1 . .
C C5 0.26737(18) 0.47099(12) 0.4848(2) 0.0218(3) Uani d . 1 . .
C C6 0.22820(18) 0.40586(13) 0.5865(2) 0.0239(4) Uani d . 1 . .
H H6 0.2436 0.3386 0.5781 0.029 Uiso calc R 1 . .
C C7 0.16682(18) 0.43931(13) 0.6996(2) 0.0243(4) Uani d . 1 . .
C C8 0.13991(18) 0.53629(13) 0.7192(2) 0.0241(4) Uani d . 1 . .
C C9 0.17893(19) 0.59892(13) 0.6130(2) 0.0254(4) Uani d . 1 . .
C C10 0.23982(18) 0.56857(13) 0.4983(2) 0.0238(4) Uani d . 1 . .
H H10 0.2630 0.6143 0.4284 0.029 Uiso calc R 1 . .
C C11 0.0760(2) 0.57125(15) 0.8451(2) 0.0332(4) Uani d . 1 . .
H H11C 0.1557 0.5816 0.9551 0.050 Uiso calc R 1 . .
H H11A 0.0072 0.5229 0.8573 0.050 Uiso calc R 1 . .
H H11B 0.0235 0.6321 0.8053 0.050 Uiso calc R 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
N2 N1 C1 . . 127.50(15) ?
N2 N1 H1 . . 116.2 ?
C1 N1 H1 . . 116.2 ?
C4 N2 N1 . . 117.27(15) ?
O1 C1 N1 . . 120.54(16) ?
O1 C1 C2 . . 125.54(17) ?
N1 C1 C2 . . 113.92(16) ?
C3 C2 C1 . . 120.00(17) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
C2 C3 C4 . . 120.11(16) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
N2 C4 C3 . . 121.12(16) ?
N2 C4 C5 . . 116.03(15) ?
C3 C4 C5 . . 122.79(15) ?
C10 C5 C6 . . 118.21(16) ?
C10 C5 C4 . . 120.12(15) ?
C6 C5 C4 . . 121.67(16) ?
C7 C6 C5 . . 119.90(17) ?
C7 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
C6 C7 C8 . . 123.71(16) ?
C6 C7 Cl1 . . 117.35(14) ?
C8 C7 Cl1 . . 118.93(14) ?
C7 C8 C9 . . 114.45(16) ?
C7 C8 C11 . . 122.88(17) ?
C9 C8 C11 . . 122.67(17) ?
C10 C9 C8 . . 123.67(17) ?
C10 C9 Cl2 . . 117.27(14) ?
C8 C9 Cl2 . . 119.06(14) ?
C9 C10 C5 . . 120.05(16) ?
C9 C10 H10 . . 120.0 ?
C5 C10 H10 . . 120.0 ?
C8 C11 H11C . . 109.5 ?
C8 C11 H11A . . 109.5 ?
H11C C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
H11C C11 H11B . . 109.5 ?
H11A C11 H11B . . 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 C7 . 1.7404(18) ?
Cl2 C9 . 1.733(2) ?
O1 C1 . 1.244(2) ?
N1 N2 . 1.345(2) ?
N1 C1 . 1.367(2) ?
N1 H1 . 0.8800 ?
N2 C4 . 1.311(2) ?
C1 C2 . 1.435(3) ?
C2 C3 . 1.347(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.425(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.485(2) ?
C5 C10 . 1.391(3) ?
C5 C6 . 1.395(2) ?
C6 C7 . 1.384(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.390(3) ?
C8 C9 . 1.400(3) ?
C8 C11 . 1.500(2) ?
C9 C10 . 1.378(2) ?
C10 H10 . 0.9500 ?
C11 H11C . 0.9800 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
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_665 0.88 1.90 2.771(2) 172.2
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
C1 N1 N2 C4 . . . . -0.2(3) ?
N2 N1 C1 O1 . . . . 178.37(16) ?
N2 N1 C1 C2 . . . . -2.0(3) ?
O1 C1 C2 C3 . . . . -177.86(17) ?
N1 C1 C2 C3 . . . . 2.6(2) ?
C1 C2 C3 C4 . . . . -1.1(3) ?
N1 N2 C4 C3 . . . . 1.9(2) ?
N1 N2 C4 C5 . . . . 179.33(14) ?
C2 C3 C4 N2 . . . . -1.3(3) ?
C2 C3 C4 C5 . . . . -178.51(16) ?
N2 C4 C5 C10 . . . . -6.9(2) ?
C3 C4 C5 C10 . . . . 170.44(16) ?
N2 C4 C5 C6 . . . . 173.38(16) ?
C3 C4 C5 C6 . . . . -9.3(3) ?
C10 C5 C6 C7 . . . . -1.5(3) ?
C4 C5 C6 C7 . . . . 178.27(15) ?
C5 C6 C7 C8 . . . . 0.3(3) ?
C5 C6 C7 Cl1 . . . . 179.41(13) ?
C6 C7 C8 C9 . . . . 0.6(3) ?
Cl1 C7 C8 C9 . . . . -178.51(13) ?
C6 C7 C8 C11 . . . . -178.75(17) ?
Cl1 C7 C8 C11 . . . . 2.2(2) ?
C7 C8 C9 C10 . . . . -0.3(3) ?
C11 C8 C9 C10 . . . . 178.98(17) ?
C7 C8 C9 Cl2 . . . . -179.37(13) ?
C11 C8 C9 Cl2 . . . . -0.1(2) ?
C8 C9 C10 C5 . . . . -0.8(3) ?
Cl2 C9 C10 C5 . . . . 178.26(13) ?
C6 C5 C10 C9 . . . . 1.7(3) ?
C4 C5 C10 C9 . . . . -178.06(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 84266
