#------------------------------------------------------------------------------
#$Date: 2015-10-15 08:17:28 +0200 (jue 15 de oct de 2015) $
#$Revision: 169178 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/29/7222976.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_7222976
loop_
_publ_author_name
'Behbehani, Haider'
'Ibrahim, Hamada Mohamed'
_publ_section_title
;
 Microwave-Assisted Synthesis in Water: First one-pot Synthesis of A novel
 Class of Polysubstituted Benzo[4,5]imidazo[1,2-b]pyridazines via
 Intramolecular SNAr
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA17313B
_journal_year                    2015
_chemical_formula_sum            'C25 H16 N4 O5'
_chemical_formula_weight         452.42
_chemical_name_common            Hamada_FK130C_23_03_15
_chemical_name_systematic        4g
_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'
_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_update_record
;
2015-09-17 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.677(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2274(4)
_cell_length_b                   7.0898(2)
_cell_length_c                   21.0075(6)
_cell_measurement_reflns_used    7101
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      66.0109
_cell_measurement_theta_min      4.0146
_cell_volume                     2100.02(10)
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_collection       'Bruker Instrument Service v2012.4.0.0'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_molecular_graphics    'Mercury 3.1'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11406
_diffrn_reflns_theta_full        66.15
_diffrn_reflns_theta_max         66.15
_diffrn_reflns_theta_min         4.93
_diffrn_source_type              'Incoatec Cu-ImS'
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0511
_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)+(0.0590P)²+1.6545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1569
_reflns_number_gt                2807
_reflns_number_total             3477
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra17313b2.cif
_cod_data_source_block           4g
_cod_database_code               7222976
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_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
O O5 0.42408(14) 0.2051(3) 1.07656(9) 0.0620(6) Uani d . 1
O O4 0.45818(14) 0.4442(3) 0.79118(9) 0.0644(6) Uani d . 1
N N1 0.86551(15) 0.1984(4) 0.75687(11) 0.0528(6) Uani d . 1
O O3 0.7914(2) -0.4763(4) 0.93132(15) 0.1033(10) Uani d . 1
O O1 0.76146(17) 0.7368(3) 0.71232(10) 0.0704(6) Uani d . 1
N N3 0.74140(14) 0.1561(3) 0.81167(9) 0.0428(5) Uani d . 1
C C20 0.56831(17) 0.2871(4) 0.94745(12) 0.0459(6) Uani d . 1
H H20 0.6315 0.2885 0.9404 0.055 Uiso calc R 1
C C17 0.64879(18) 0.4643(4) 0.76775(12) 0.0478(6) Uani d . 1
H H17 0.6138 0.571 0.754 0.057 Uiso calc R 1
C C9 0.78343(17) 0.2665(4) 0.76808(12) 0.0465(6) Uani d . 1
O O2 0.9282(2) -0.5545(5) 0.91162(18) 0.1304(13) Uani d . 1
N N2 0.8624(2) -0.4465(4) 0.90742(13) 0.0704(7) Uani d . 1
C C13 0.8677(2) -0.2739(4) 0.86936(13) 0.0531(7) Uani d . 1
C C14 0.79373(19) -0.1484(4) 0.86696(12) 0.0483(6) Uani d . 1
H H14 0.7425 -0.1661 0.8896 0.058 Uiso calc R 1
C C15 0.80189(17) 0.0063(4) 0.82819(11) 0.0428(6) Uani d . 1
N N4 0.65847(14) 0.1873(3) 0.83401(9) 0.0439(5) Uani d . 1
C C16 0.61413(18) 0.3403(4) 0.81193(11) 0.0435(6) Uani d . 1
C C18 0.51785(18) 0.3752(4) 0.83206(12) 0.0452(6) Uani d . 1
C C19 0.49790(17) 0.3283(4) 0.89685(12) 0.0424(6) Uani d . 1
C C24 0.40369(18) 0.3279(4) 0.90910(13) 0.0486(6) Uani d . 1
H H24 0.3555 0.3574 0.8762 0.058 Uiso calc R 1
C C23 0.38123(18) 0.2846(4) 0.96895(13) 0.0522(7) Uani d . 1
H H23 0.3182 0.2826 0.9762 0.063 Uiso calc R 1
C C22 0.45315(19) 0.2435(4) 1.01892(13) 0.0475(6) Uani d . 1
C C25 0.4957(2) 0.1572(5) 1.12849(14) 0.0627(8) Uani d . 1
H H25A 0.5289 0.0466 1.1175 0.094 Uiso calc R 1
H H25B 0.4666 0.1328 1.1664 0.094 Uiso calc R 1
H H25C 0.5395 0.26 1.1365 0.094 Uiso calc R 1
C C21 0.54649(18) 0.2444(4) 1.00782(12) 0.0474(6) Uani d . 1
H H21 0.5946 0.2162 1.0409 0.057 Uiso calc R 1
C C8 0.73200(18) 0.4308(4) 0.74505(11) 0.0466(6) Uani d . 1
C C10 0.87796(17) 0.0364(4) 0.79366(12) 0.0477(6) Uani d . 1
C C12 0.9456(2) -0.2499(5) 0.83632(14) 0.0589(8) Uani d . 1
H H12 0.9939 -0.3394 0.8403 0.071 Uiso calc R 1
C C11 0.95125(19) -0.0952(5) 0.79811(14) 0.0597(8) Uani d . 1
H H11 1.0027 -0.0783 0.7757 0.072 Uiso calc R 1
C C7 0.76892(19) 0.5701(5) 0.69994(12) 0.0518(7) Uani d . 1
C C4 0.80586(18) 0.5068(5) 0.64117(12) 0.0554(8) Uani d . 1
C C5 0.8579(2) 0.6339(6) 0.60943(16) 0.0760(10) Uani d . 1
H H5 0.8716 0.7533 0.6265 0.091 Uiso calc R 1
C C6 0.8891(3) 0.5821(9) 0.5525(2) 0.0984(15) Uani d . 1
H H6 0.9247 0.6661 0.5315 0.118 Uiso calc R 1
C C1 0.8678(3) 0.4070(9) 0.52676(19) 0.1046(16) Uani d . 1
H H1 0.8881 0.3738 0.488 0.126 Uiso calc R 1
C C2 0.8169(3) 0.2809(7) 0.55752(17) 0.0885(12) Uani d . 1
H H2 0.803 0.1622 0.5399 0.106 Uiso calc R 1
C C3 0.7860(2) 0.3306(6) 0.61515(14) 0.0671(9) Uani d . 1
H H3 0.7517 0.2446 0.6363 0.081 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C22 O5 C25 117.2(2)
C9 N1 C10 104.8(2)
N4 N3 C15 125.8(2)
N4 N3 C9 127.5(2)
C15 N3 C9 106.76(19)
C21 C20 C19 121.4(2)
C21 C20 H20 119.3
C19 C20 H20 119.3
C8 C17 C16 121.3(3)
C8 C17 H17 119.4
C16 C17 H17 119.4
N1 C9 N3 112.3(2)
N1 C9 C8 131.9(2)
N3 C9 C8 115.8(2)
O2 N2 O3 123.0(3)
O2 N2 C13 118.3(3)
O3 N2 C13 118.7(3)
C14 C13 C12 124.0(3)
C14 C13 N2 117.7(3)
C12 C13 N2 118.3(3)
C13 C14 C15 114.3(2)
C13 C14 H14 122.8
C15 C14 H14 122.8
C14 C15 N3 131.3(2)
C14 C15 C10 124.1(2)
N3 C15 C10 104.6(2)
C16 N4 N3 114.6(2)
N4 C16 C17 123.7(2)
N4 C16 C18 116.7(2)
C17 C16 C18 119.5(2)
O4 C18 C19 122.6(2)
O4 C18 C16 116.1(2)
C19 C18 C16 121.3(2)
C20 C19 C24 118.0(2)
C20 C19 C18 123.3(2)
C24 C19 C18 118.8(2)
C23 C24 C19 121.0(2)
C23 C24 H24 119.5
C19 C24 H24 119.5
C24 C23 C22 119.9(2)
C24 C23 H23 120.0
C22 C23 H23 120.0
O5 C22 C21 124.5(3)
O5 C22 C23 115.6(2)
C21 C22 C23 119.9(2)
O5 C25 H25A 109.5
O5 C25 H25B 109.5
H25A C25 H25B 109.5
O5 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
C20 C21 C22 119.8(3)
C20 C21 H21 120.1
C22 C21 H21 120.1
C17 C8 C9 117.2(2)
C17 C8 C7 119.9(3)
C9 C8 C7 122.8(2)
N1 C10 C11 129.3(2)
N1 C10 C15 111.5(2)
C11 C10 C15 119.2(3)
C11 C12 C13 120.2(3)
C11 C12 H12 119.9
C13 C12 H12 119.9
C12 C11 C10 118.3(3)
C12 C11 H11 120.8
C10 C11 H11 120.8
O1 C7 C4 121.7(3)
O1 C7 C8 116.9(3)
C4 C7 C8 121.2(3)
C3 C4 C5 119.4(3)
C3 C4 C7 122.1(3)
C5 C4 C7 118.4(3)
C6 C5 C4 119.8(4)
C6 C5 H5 120.1
C4 C5 H5 120.1
C1 C6 C5 120.2(4)
C1 C6 H6 119.9
C5 C6 H6 119.9
C2 C1 C6 120.6(4)
C2 C1 H1 119.7
C6 C1 H1 119.7
C1 C2 C3 119.8(4)
C1 C2 H2 120.1
C3 C2 H2 120.1
C4 C3 C2 120.3(4)
C4 C3 H3 119.9
C2 C3 H3 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O5 C22 1.358(3)
O5 C25 1.430(4)
O4 C18 1.226(3)
N1 C9 1.314(3)
N1 C10 1.383(4)
O3 N2 1.205(4)
O1 C7 1.218(4)
N3 N4 1.345(3)
N3 C15 1.382(3)
N3 C9 1.398(3)
C20 C21 1.379(4)
C20 C19 1.391(4)
C20 H20 0.93
C17 C8 1.355(4)
C17 C16 1.414(4)
C17 H17 0.93
C9 C8 1.425(4)
O2 N2 1.204(4)
N2 C13 1.469(4)
C13 C14 1.374(4)
C13 C12 1.395(4)
C14 C15 1.380(4)
C14 H14 0.93
C15 C10 1.397(3)
N4 C16 1.309(3)
C16 C18 1.507(3)
C18 C19 1.465(3)
C19 C24 1.398(3)
C24 C23 1.373(4)
C24 H24 0.93
C23 C22 1.395(4)
C23 H23 0.93
C22 C21 1.379(4)
C25 H25A 0.96
C25 H25B 0.96
C25 H25C 0.96
C21 H21 0.93
C8 C7 1.511(4)
C10 C11 1.393(4)
C12 C11 1.368(4)
C12 H12 0.93
C11 H11 0.93
C7 C4 1.475(4)
C4 C3 1.378(5)
C4 C5 1.392(4)
C5 C6 1.380(6)
C5 H5 0.93
C6 C1 1.372(7)
C6 H6 0.93
C1 C2 1.366(6)
C1 H1 0.93
C2 C3 1.388(4)
C2 H2 0.93
C3 H3 0.93
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
C10 N1 C9 N3 0.7(3)
C10 N1 C9 C8 179.4(3)
N4 N3 C9 N1 179.1(2)
C15 N3 C9 N1 -0.8(3)
N4 N3 C9 C8 0.1(4)
C15 N3 C9 C8 -179.7(2)
O2 N2 C13 C14 -177.6(3)
O3 N2 C13 C14 4.7(4)
O2 N2 C13 C12 4.4(5)
O3 N2 C13 C12 -173.4(3)
C12 C13 C14 C15 0.5(4)
N2 C13 C14 C15 -177.4(2)
C13 C14 C15 N3 177.0(3)
C13 C14 C15 C10 0.1(4)
N4 N3 C15 C14 3.3(4)
C9 N3 C15 C14 -176.8(3)
N4 N3 C15 C10 -179.3(2)
C9 N3 C15 C10 0.5(3)
C15 N3 N4 C16 179.2(2)
C9 N3 N4 C16 -0.6(3)
N3 N4 C16 C17 0.5(3)
N3 N4 C16 C18 176.1(2)
C8 C17 C16 N4 0.1(4)
C8 C17 C16 C18 -175.4(2)
N4 C16 C18 O4 -142.6(3)
C17 C16 C18 O4 33.2(4)
N4 C16 C18 C19 37.3(4)
C17 C16 C18 C19 -146.8(3)
C21 C20 C19 C24 0.9(4)
C21 C20 C19 C18 179.8(3)
O4 C18 C19 C20 -166.3(3)
C16 C18 C19 C20 13.8(4)
O4 C18 C19 C24 12.5(4)
C16 C18 C19 C24 -167.4(2)
C20 C19 C24 C23 -1.2(4)
C18 C19 C24 C23 179.9(3)
C19 C24 C23 C22 1.2(4)
C25 O5 C22 C21 -1.8(4)
C25 O5 C22 C23 178.3(3)
C24 C23 C22 O5 179.1(3)
C24 C23 C22 C21 -0.8(4)
C19 C20 C21 C22 -0.5(4)
O5 C22 C21 C20 -179.4(3)
C23 C22 C21 C20 0.5(4)
C16 C17 C8 C9 -0.6(4)
C16 C17 C8 C7 -177.6(2)
N1 C9 C8 C17 -178.2(3)
N3 C9 C8 C17 0.5(3)
N1 C9 C8 C7 -1.3(5)
N3 C9 C8 C7 177.3(2)
C9 N1 C10 C11 177.2(3)
C9 N1 C10 C15 -0.3(3)
C14 C15 C10 N1 177.5(2)
N3 C15 C10 N1 -0.1(3)
C14 C15 C10 C11 -0.4(4)
N3 C15 C10 C11 -178.0(2)
C14 C13 C12 C11 -0.7(5)
N2 C13 C12 C11 177.2(3)
C13 C12 C11 C10 0.4(4)
N1 C10 C11 C12 -177.3(3)
C15 C10 C11 C12 0.1(4)
C17 C8 C7 O1 41.7(4)
C9 C8 C7 O1 -135.1(3)
C17 C8 C7 C4 -134.0(3)
C9 C8 C7 C4 49.2(4)
O1 C7 C4 C3 -157.6(3)
C8 C7 C4 C3 17.9(4)
O1 C7 C4 C5 18.7(4)
C8 C7 C4 C5 -165.7(3)
C3 C4 C5 C6 -0.1(5)
C7 C4 C5 C6 -176.6(3)
C4 C5 C6 C1 0.9(6)
C5 C6 C1 C2 -1.1(7)
C6 C1 C2 C3 0.3(6)
C5 C4 C3 C2 -0.6(5)
C7 C4 C3 C2 175.7(3)
C1 C2 C3 C4 0.5(5)
