#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/52/2225262.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_2225262
loop_
_publ_author_name
'Wang, Hongliang'
'Xiao, Junhai'
'Zhang, Xian'
'Sun, Tiemin'
'Li, Song'
_publ_section_title
;
 3-Chloro-6-{4-[3-(4-chlorophenoxy)propyl]piperazin-1-yl}pyridazine
;
_journal_coeditor_code           HB5330
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o716
_journal_paper_doi               10.1107/S1600536810005337
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H20 Cl2 N4 O'
_chemical_formula_moiety         'C17 H20 Cl2 N4 O'
_chemical_formula_sum            'C17 H20 Cl2 N4 O'
_chemical_formula_weight         367.27
_chemical_name_systematic
;
3-Chloro-6-{4-[3-(4-chlorophenoxy)propyl]piperazin-1-yl}pyridazine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 93.107(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   39.774(18)
_cell_length_b                   5.757(3)
_cell_length_c                   14.924(7)
_cell_measurement_reflns_used    5597
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.1
_cell_volume                     3412(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11904
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.328
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0834P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1590
_reflns_number_gt                2030
_reflns_number_total             2996
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5330.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2225262
_cod_database_fobs_code          2225262
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 1.06826(2) -0.31802(19) 0.30198(6) 0.0238(3) Uani d . 1 . .
Cl Cl2 0.64299(2) 0.03379(19) 0.75503(6) 0.0252(3) Uani d . 1 . .
O O1 0.77076(5) 0.0299(4) 0.57543(16) 0.0172(6) Uani d . 1 . .
N N1 1.01144(7) -0.4149(6) 0.37004(19) 0.0191(8) Uani d . 1 . .
N N2 0.98066(6) -0.3697(6) 0.40118(19) 0.0177(7) Uani d . 1 . .
N N3 0.93922(6) -0.1129(5) 0.44101(19) 0.0159(7) Uani d . 1 . .
N N4 0.87083(6) -0.0635(5) 0.49145(19) 0.0149(7) Uani d . 1 . .
C C1 1.02999(8) -0.2401(7) 0.3457(2) 0.0177(9) Uani d . 1 . .
C C2 1.02128(8) -0.0067(7) 0.3520(2) 0.0182(9) Uani d . 1 . .
H H2 1.0360 0.1133 0.3349 0.022 Uiso calc R 1 . .
C C3 0.99070(8) 0.0412(7) 0.3837(2) 0.0182(8) Uani d . 1 . .
H H3 0.9832 0.1967 0.3898 0.022 Uiso calc R 1 . .
C C4 0.97035(8) -0.1495(7) 0.4072(2) 0.0154(8) Uani d . 1 . .
C C5 0.92000(8) -0.3152(7) 0.4675(2) 0.0180(8) Uani d . 1 . .
H H5A 0.9353 -0.4301 0.4975 0.022 Uiso calc R 1 . .
H H5B 0.9090 -0.3892 0.4137 0.022 Uiso calc R 1 . .
C C6 0.89344(8) -0.2413(7) 0.5311(2) 0.0179(9) Uani d . 1 . .
H H6A 0.8800 -0.3786 0.5471 0.021 Uiso calc R 1 . .
H H6B 0.9047 -0.1797 0.5869 0.021 Uiso calc R 1 . .
C C7 0.89091(8) 0.1374(7) 0.4665(2) 0.0156(8) Uani d . 1 . .
H H7A 0.9021 0.2057 0.5212 0.019 Uiso calc R 1 . .
H H7B 0.8759 0.2569 0.4384 0.019 Uiso calc R 1 . .
C C8 0.91722(8) 0.0697(7) 0.4018(2) 0.0164(8) Uani d . 1 . .
H H8A 0.9060 0.0130 0.3451 0.020 Uiso calc R 1 . .
H H8B 0.9309 0.2074 0.3879 0.020 Uiso calc R 1 . .
C C9 0.84595(8) -0.0032(7) 0.5562(2) 0.0169(8) Uani d . 1 . .
H H9A 0.8579 0.0471 0.6128 0.020 Uiso calc R 1 . .
H H9B 0.8328 -0.1438 0.5694 0.020 Uiso calc R 1 . .
C C10 0.82186(8) 0.1877(7) 0.5241(2) 0.0169(8) Uani d . 1 . .
H H10A 0.8346 0.3345 0.5193 0.020 Uiso calc R 1 . .
H H10B 0.8123 0.1478 0.4635 0.020 Uiso calc R 1 . .
C C11 0.79342(8) 0.2255(7) 0.5855(2) 0.0158(8) Uani d . 1 . .
H H11A 0.8024 0.2378 0.6485 0.019 Uiso calc R 1 . .
H H11B 0.7814 0.3713 0.5693 0.019 Uiso calc R 1 . .
C C12 0.74176(8) 0.0403(7) 0.6207(2) 0.0146(8) Uani d . 1 . .
C C13 0.71859(8) -0.1366(7) 0.6022(2) 0.0171(8) Uani d . 1 . .
H H13 0.7236 -0.2563 0.5612 0.020 Uiso calc R 1 . .
C C14 0.68822(8) -0.1390(7) 0.6433(2) 0.0163(8) Uani d . 1 . .
H H14 0.6723 -0.2587 0.6301 0.020 Uiso calc R 1 . .
C C15 0.68135(8) 0.0346(7) 0.7035(2) 0.0169(8) Uani d . 1 . .
C C16 0.70436(8) 0.2093(7) 0.7240(2) 0.0181(8) Uani d . 1 . .
H H16 0.6995 0.3259 0.7664 0.022 Uiso calc R 1 . .
C C17 0.73474(8) 0.2130(7) 0.6819(2) 0.0167(8) Uani d . 1 . .
H H17 0.7506 0.3331 0.6951 0.020 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
C12 O1 C11 . . 116.9(3) ?
C1 N1 N2 . . 118.6(3) ?
C4 N2 N1 . . 119.4(3) ?
C4 N3 C5 . . 118.2(3) ?
C4 N3 C8 . . 119.4(3) ?
C5 N3 C8 . . 111.7(3) ?
C9 N4 C7 . . 112.2(3) ?
C9 N4 C6 . . 108.8(3) ?
C7 N4 C6 . . 108.8(3) ?
N1 C1 C2 . . 125.2(3) ?
N1 C1 Cl1 . . 114.9(3) ?
C2 C1 Cl1 . . 119.9(3) ?
C3 C2 C1 . . 116.8(3) ?
C3 C2 H2 . . 121.6 ?
C1 C2 H2 . . 121.6 ?
C2 C3 C4 . . 117.6(4) ?
C2 C3 H3 . . 121.2 ?
C4 C3 H3 . . 121.2 ?
N2 C4 N3 . . 117.0(3) ?
N2 C4 C3 . . 122.4(3) ?
N3 C4 C3 . . 120.5(3) ?
N3 C5 C6 . . 109.8(3) ?
N3 C5 H5A . . 109.7 ?
C6 C5 H5A . . 109.7 ?
N3 C5 H5B . . 109.7 ?
C6 C5 H5B . . 109.7 ?
H5A C5 H5B . . 108.2 ?
N4 C6 C5 . . 112.1(3) ?
N4 C6 H6A . . 109.2 ?
C5 C6 H6A . . 109.2 ?
N4 C6 H6B . . 109.2 ?
C5 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
N4 C7 C8 . . 111.3(3) ?
N4 C7 H7A . . 109.4 ?
C8 C7 H7A . . 109.4 ?
N4 C7 H7B . . 109.4 ?
C8 C7 H7B . . 109.4 ?
H7A C7 H7B . . 108.0 ?
N3 C8 C7 . . 110.4(3) ?
N3 C8 H8A . . 109.6 ?
C7 C8 H8A . . 109.6 ?
N3 C8 H8B . . 109.6 ?
C7 C8 H8B . . 109.6 ?
H8A C8 H8B . . 108.1 ?
N4 C9 C10 . . 113.7(3) ?
N4 C9 H9A . . 108.8 ?
C10 C9 H9A . . 108.8 ?
N4 C9 H9B . . 108.8 ?
C10 C9 H9B . . 108.8 ?
H9A C9 H9B . . 107.7 ?
C11 C10 C9 . . 113.2(3) ?
C11 C10 H10A . . 108.9 ?
C9 C10 H10A . . 108.9 ?
C11 C10 H10B . . 108.9 ?
C9 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.7 ?
O1 C11 C10 . . 108.0(3) ?
O1 C11 H11A . . 110.1 ?
C10 C11 H11A . . 110.1 ?
O1 C11 H11B . . 110.1 ?
C10 C11 H11B . . 110.1 ?
H11A C11 H11B . . 108.4 ?
O1 C12 C17 . . 124.1(3) ?
O1 C12 C13 . . 115.9(3) ?
C17 C12 C13 . . 120.0(3) ?
C14 C13 C12 . . 120.3(3) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C15 C14 C13 . . 119.3(3) ?
C15 C14 H14 . . 120.4 ?
C13 C14 H14 . . 120.4 ?
C14 C15 C16 . . 121.2(3) ?
C14 C15 Cl2 . . 119.6(3) ?
C16 C15 Cl2 . . 119.3(3) ?
C15 C16 C17 . . 119.5(4) ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C12 C17 C16 . . 119.8(3) ?
C12 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
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 C1 . 1.747(3) ?
Cl2 C15 . 1.745(3) ?
O1 C12 . 1.369(4) ?
O1 C11 . 1.445(4) ?
N1 C1 . 1.311(5) ?
N1 N2 . 1.358(4) ?
N2 C4 . 1.337(5) ?
N3 C4 . 1.378(4) ?
N3 C5 . 1.459(5) ?
N3 C8 . 1.469(4) ?
N4 C9 . 1.462(4) ?
N4 C7 . 1.465(4) ?
N4 C6 . 1.466(4) ?
C1 C2 . 1.392(5) ?
C2 C3 . 1.357(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.419(5) ?
C3 H3 . 0.9500 ?
C5 C6 . 1.518(5) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.513(4) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.518(5) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.509(5) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C17 . 1.389(5) ?
C12 C13 . 1.391(5) ?
C13 C14 . 1.383(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.382(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.383(5) ?
C16 C17 . 1.392(5) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
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
C3 H3 N1 1_565 0.95 2.53 3.247(6) 133
C3 H3 N2 1_565 0.95 2.50 3.427(6) 164
C13 H13 O1 7_646 0.95 2.60 3.529(5) 168
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 . . . . -0.9(5) ?
N2 N1 C1 C2 . . . . 2.5(5) ?
N2 N1 C1 Cl1 . . . . -177.3(2) ?
N1 C1 C2 C3 . . . . -1.9(5) ?
Cl1 C1 C2 C3 . . . . 177.8(2) ?
C1 C2 C3 C4 . . . . -0.2(5) ?
N1 N2 C4 N3 . . . . -178.7(3) ?
N1 N2 C4 C3 . . . . -1.1(5) ?
C5 N3 C4 N2 . . . . 0.0(5) ?
C8 N3 C4 N2 . . . . -141.5(3) ?
C5 N3 C4 C3 . . . . -177.5(3) ?
C8 N3 C4 C3 . . . . 41.0(5) ?
C2 C3 C4 N2 . . . . 1.6(5) ?
C2 C3 C4 N3 . . . . 179.1(3) ?
C4 N3 C5 C6 . . . . 160.3(3) ?
C8 N3 C5 C6 . . . . -55.4(4) ?
C9 N4 C6 C5 . . . . 179.6(3) ?
C7 N4 C6 C5 . . . . -57.9(4) ?
N3 C5 C6 N4 . . . . 57.0(4) ?
C9 N4 C7 C8 . . . . 178.2(3) ?
C6 N4 C7 C8 . . . . 57.7(3) ?
C4 N3 C8 C7 . . . . -160.2(3) ?
C5 N3 C8 C7 . . . . 56.0(4) ?
N4 C7 C8 N3 . . . . -57.3(4) ?
C7 N4 C9 C10 . . . . 57.1(4) ?
C6 N4 C9 C10 . . . . 177.6(3) ?
N4 C9 C10 C11 . . . . 172.0(3) ?
C12 O1 C11 C10 . . . . -175.1(3) ?
C9 C10 C11 O1 . . . . -71.7(4) ?
C11 O1 C12 C17 . . . . -7.1(5) ?
C11 O1 C12 C13 . . . . 173.0(3) ?
O1 C12 C13 C14 . . . . -178.8(3) ?
C17 C12 C13 C14 . . . . 1.3(5) ?
C12 C13 C14 C15 . . . . -0.8(5) ?
C13 C14 C15 C16 . . . . -0.5(5) ?
C13 C14 C15 Cl2 . . . . 179.6(3) ?
C14 C15 C16 C17 . . . . 1.2(5) ?
Cl2 C15 C16 C17 . . . . -178.9(3) ?
O1 C12 C17 C16 . . . . 179.5(3) ?
C13 C12 C17 C16 . . . . -0.6(5) ?
C15 C16 C17 C12 . . . . -0.6(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744501
