#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/17/8101785.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_8101785
loop_
_publ_author_name
'T. Irrgang'
'R. Kempe'
_publ_section_title
;
Crystal structure of N,N'-bis(2,4-dimethyl-5-phenylimidazo[1,5-b]pyridazin-
7-yl)-1,3-diaminopropane, C₃₁H₃₂N₈
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              403
_journal_page_last               404
_journal_volume                  220
_journal_year                    2005
_chemical_formula_sum            'C31 H32 N8'
_chemical_formula_weight         516.65
_chemical_name_systematic
N,N'-bis(2,4-dimethyl-5-phenylimidazo[1,5-b]pyridazin-7-yl)-1,3-diaminopropane
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 100.920(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   9.581(1)
_cell_length_b                   16.381(2)
_cell_length_c                   17.803(2)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      4
_cell_volume                     2743.5(5)
_computing_cell_refinement       Stoe-Cell
_computing_data_collection       Stoe-Expose
_computing_data_reduction        Stoe-Reduce
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Stoe IPDS I'
_diffrn_measurement_method       phi
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.1013
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8071
_diffrn_reflns_theta_full        24.36
_diffrn_reflns_theta_max         24.36
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.790
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         4147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.790
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0483P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1111
_reflns_number_gt                1966
_reflns_number_total             4147
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1539.cff
_cod_data_source_block           460
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'no' was replaced with
'none' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2743(1)
_cod_original_sg_symbol_H-M      P12(1)/a1
_cod_database_code               8101785
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
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_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2450(3) 0.21815(17) 0.16482(14) 0.0495(8) Uani 1 4 e d . . .
N2 N 0.0196(3) 0.15312(15) 0.15829(13) 0.0443(7) Uani 1 4 e d . . .
N3 N 0.1063(3) 0.16662(14) 0.05214(12) 0.0421(6) Uani 1 4 e d . . .
N4 N 0.2044(3) 0.18724(14) 0.00720(14) 0.0474(7) Uani 1 4 e d . . .
N5 N 0.1865(3) 0.09331(17) 0.33217(14) 0.0506(8) Uani 1 4 e d . . .
N6 N 0.3141(3) 0.10829(16) 0.46054(13) 0.0493(7) Uani 1 4 e d . . .
N7 N 0.0789(3) 0.10989(15) 0.44221(12) 0.0454(7) Uani 1 4 e d . . .
N8 N -0.0575(3) 0.11046(16) 0.40264(13) 0.0514(7) Uani 1 4 e d . . .
C1 C 0.2744(4) 0.1823(2) -0.11451(19) 0.0789(12) Uani 1 4 e d . . .
H1A H 0.3525 0.2125 -0.0857 0.118 Uiso 1 4 e calc R . .
H1B H 0.2290 0.2142 -0.1575 0.118 Uiso 1 4 e calc R . .
H1C H 0.3090 0.1323 -0.1324 0.118 Uiso 1 4 e calc R . .
C2 C 0.1680(4) 0.1630(2) -0.06381(18) 0.0530(9) Uani 1 4 e d . . .
C3 C 0.0424(4) 0.1186(2) -0.09100(17) 0.0559(9) Uani 1 4 e d . . .
H3 H 0.0247 0.1017 -0.1418 0.067 Uiso 1 4 e calc R . .
C4 C -0.0543(4) 0.09923(18) -0.04694(17) 0.0474(8) Uani 1 4 e d . . .
C5 C -0.1837(4) 0.0497(2) -0.07689(18) 0.0657(10) Uani 1 4 e d . . .
H5A H -0.2384 0.0429 -0.0374 0.099 Uiso 1 4 e calc R . .
H5B H -0.1558 -0.0029 -0.0928 0.099 Uiso 1 4 e calc R . .
H5C H -0.2402 0.0772 -0.1197 0.099 Uiso 1 4 e calc R . .
C6 C -0.0239(3) 0.12586(17) 0.03051(15) 0.0414(8) Uani 1 4 e d . . .
C7 C -0.0769(3) 0.11916(18) 0.09811(16) 0.0412(8) Uani 1 4 e d . . .
C8 C -0.2109(3) 0.08647(18) 0.11444(17) 0.0445(8) Uani 1 4 e d . . .
C9 C -0.3393(4) 0.1020(2) 0.06729(18) 0.0568(9) Uani 1 4 e d . . .
H9 H -0.3419 0.1310 0.0221 0.068 Uiso 1 4 e calc R . .
C10 C -0.4655(4) 0.0745(2) 0.0868(2) 0.0726(11) Uani 1 4 e d . . .
H10 H -0.5518 0.0852 0.0545 0.087 Uiso 1 4 e calc R . .
C11 C -0.4633(4) 0.0318(2) 0.1531(2) 0.0724(11) Uani 1 4 e d . . .
H11 H -0.5479 0.0134 0.1656 0.087 Uiso 1 4 e calc R . .
C12 C -0.3377(4) 0.0163(2) 0.2007(2) 0.0654(10) Uani 1 4 e d . . .
H12 H -0.3361 -0.0123 0.2459 0.079 Uiso 1 4 e calc R . .
C13 C -0.2121(4) 0.04318(19) 0.18154(17) 0.0528(9) Uani 1 4 e d . . .
H13 H -0.1265 0.0321 0.2143 0.063 Uiso 1 4 e calc R . .
C14 C -0.3039(4) 0.1164(3) 0.4072(2) 0.0868(13) Uani 1 4 e d . . .
H14A H -0.3088 0.1182 0.3529 0.130 Uiso 1 4 e calc R . .
H14B H -0.3476 0.1645 0.4232 0.130 Uiso 1 4 e calc R . .
H14C H -0.3531 0.0689 0.4201 0.130 Uiso 1 4 e calc R . .
C15 C -0.1533(4) 0.1128(2) 0.44649(17) 0.0549(9) Uani 1 4 e d . . .
C16 C -0.1184(4) 0.1099(2) 0.52808(17) 0.0601(10) Uani 1 4 e d . . .
H16 H -0.1919 0.1076 0.5555 0.072 Uiso 1 4 e calc R . .
C17 C 0.0156(3) 0.11045(19) 0.56670(17) 0.0481(8) Uani 1 4 e d . . .
C18 C 0.0485(4) 0.0998(2) 0.65210(16) 0.0630(10) Uani 1 4 e d . . .
H18A H 0.1495 0.1016 0.6698 0.094 Uiso 1 4 e calc R . .
H18B H 0.0125 0.0481 0.6653 0.094 Uiso 1 4 e calc R . .
H18C H 0.0044 0.1429 0.6758 0.094 Uiso 1 4 e calc R . .
C19 C 0.1257(3) 0.11605(18) 0.52199(15) 0.0429(8) Uani 1 4 e d . . .
C20 C 0.2708(4) 0.11721(19) 0.53068(16) 0.0475(8) Uani 1 4 e d . . .
C21 C 0.3796(3) 0.13043(19) 0.59980(16) 0.0462(8) Uani 1 4 e d . . .
C22 C 0.3590(4) 0.1868(2) 0.65506(19) 0.0605(10) Uani 1 4 e d . . .
H22 H 0.2752 0.2169 0.6483 0.073 Uiso 1 4 e calc R . .
C23 C 0.4620(5) 0.1985(2) 0.71994(19) 0.0694(11) Uani 1 4 e d . . .
H23 H 0.4464 0.2349 0.7576 0.083 Uiso 1 4 e calc R . .
C24 C 0.5872(5) 0.1561(2) 0.7282(2) 0.0701(11) Uani 1 4 e d . . .
H24 H 0.6567 0.1637 0.7718 0.084 Uiso 1 4 e calc R . .
C25 C 0.6110(4) 0.1025(2) 0.6727(2) 0.0652(10) Uani 1 4 e d . . .
H25 H 0.6971 0.0749 0.6784 0.078 Uiso 1 4 e calc R . .
C26 C 0.5083(4) 0.0897(2) 0.60913(17) 0.0538(9) Uani 1 4 e d . . .
H26 H 0.5251 0.0532 0.5718 0.065 Uiso 1 4 e calc R . .
C27 C 0.1963(3) 0.10418(18) 0.40954(17) 0.0434(8) Uani 1 4 e d . . .
C28 C 0.3148(3) 0.10522(19) 0.30001(16) 0.0477(8) Uani 1 4 e d . . .
H28A H 0.2978 0.0834 0.2484 0.057 Uiso 1 4 e calc R . .
H28B H 0.3915 0.0739 0.3301 0.057 Uiso 1 4 e calc R . .
C29 C 0.3623(3) 0.19247(18) 0.29729(16) 0.0482(8) Uani 1 4 e d . . .
H29A H 0.3746 0.2154 0.3484 0.058 Uiso 1 4 e calc R . .
H29B H 0.4541 0.1934 0.2819 0.058 Uiso 1 4 e calc R . .
C30 C 0.2615(3) 0.24550(19) 0.24384(15) 0.0471(8) Uani 1 4 e d . . .
H30A H 0.1695 0.2451 0.2590 0.057 Uiso 1 4 e calc R . .
H30B H 0.2965 0.3012 0.2476 0.057 Uiso 1 4 e calc R . .
C31 C 0.1271(3) 0.18124(18) 0.12841(16) 0.0418(8) Uani 1 4 e d . . .
H200 H 0.106(3) 0.1088(17) 0.3027(17) 0.056(10) Uiso 1 4 e d . . .
H100 H 0.307(4) 0.2359(19) 0.1398(17) 0.066(11) Uiso 1 4 e d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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
_geom_angle_publ_flag
C31 N1 C30 122.4(3) . . ?
C31 N2 C7 106.4(2) . . ?
C31 N3 N4 123.2(3) . . ?
C31 N3 C6 108.3(2) . . ?
N4 N3 C6 128.5(2) . . ?
C2 N4 N3 113.5(3) . . ?
C27 N5 C28 118.1(3) . . ?
C27 N6 C20 105.2(3) . . ?
N8 N7 C27 124.6(2) . . ?
N8 N7 C19 127.7(2) . . ?
C27 N7 C19 107.7(2) . . ?
C15 N8 N7 113.8(2) . . ?
N4 C2 C3 122.8(3) . . ?
N4 C2 C1 115.2(3) . . ?
C3 C2 C1 121.9(3) . . ?
C4 C3 C2 123.5(3) . . ?
C3 C4 C6 116.8(3) . . ?
C3 C4 C5 122.1(3) . . ?
C6 C4 C5 121.1(3) . . ?
C7 C6 N3 104.5(2) . . ?
C7 C6 C4 140.3(3) . . ?
N3 C6 C4 114.9(3) . . ?
N2 C7 C6 109.6(3) . . ?
N2 C7 C8 118.1(2) . . ?
C6 C7 C8 132.3(3) . . ?
C9 C8 C13 117.8(3) . . ?
C9 C8 C7 121.7(3) . . ?
C13 C8 C7 120.3(3) . . ?
C8 C9 C10 120.4(3) . . ?
C11 C10 C9 120.5(3) . . ?
C12 C11 C10 120.0(4) . . ?
C11 C12 C13 119.8(4) . . ?
C12 C13 C8 121.5(3) . . ?
N8 C15 C16 123.2(3) . . ?
N8 C15 C14 116.7(3) . . ?
C16 C15 C14 120.1(3) . . ?
C17 C16 C15 122.7(3) . . ?
C16 C17 C19 116.7(3) . . ?
C16 C17 C18 121.0(3) . . ?
C19 C17 C18 122.1(3) . . ?
C20 C19 N7 103.7(2) . . ?
C20 C19 C17 140.6(3) . . ?
N7 C19 C17 115.2(3) . . ?
C19 C20 N6 111.4(3) . . ?
C19 C20 C21 129.8(3) . . ?
N6 C20 C21 118.7(3) . . ?
C26 C21 C22 118.6(3) . . ?
C26 C21 C20 120.2(3) . . ?
C22 C21 C20 121.1(3) . . ?
C23 C22 C21 120.6(4) . . ?
C24 C23 C22 119.4(4) . . ?
C23 C24 C25 120.6(3) . . ?
C26 C25 C24 120.2(4) . . ?
C25 C26 C21 120.7(3) . . ?
N6 C27 N7 111.9(3) . . ?
N6 C27 N5 126.0(3) . . ?
N7 C27 N5 122.1(3) . . ?
N5 C28 C29 114.9(3) . . ?
C30 C29 C28 114.2(3) . . ?
N1 C30 C29 112.0(3) . . ?
N2 C31 N1 127.7(3) . . ?
N2 C31 N3 111.2(3) . . ?
N1 C31 N3 121.1(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C31 1.335(4) . ?
N1 C30 1.456(3) . ?
N2 C31 1.328(4) . ?
N2 C7 1.391(3) . ?
N3 C31 1.356(3) . ?
N3 N4 1.386(3) . ?
N3 C6 1.403(4) . ?
N4 C2 1.308(4) . ?
N5 C27 1.374(4) . ?
N5 C28 1.464(4) . ?
N6 C27 1.309(4) . ?
N6 C20 1.396(3) . ?
N7 N8 1.362(3) . ?
N7 C27 1.364(4) . ?
N7 C19 1.410(3) . ?
N8 C15 1.313(4) . ?
C1 C2 1.517(4) . ?
C2 C3 1.411(5) . ?
C3 C4 1.360(4) . ?
C4 C6 1.423(4) . ?
C4 C5 1.493(4) . ?
C6 C7 1.397(4) . ?
C7 C8 1.470(4) . ?
C8 C9 1.375(4) . ?
C8 C13 1.391(4) . ?
C9 C10 1.395(5) . ?
C10 C11 1.369(5) . ?
C11 C12 1.358(5) . ?
C12 C13 1.383(4) . ?
C14 C15 1.481(5) . ?
C15 C16 1.428(4) . ?
C16 C17 1.337(4) . ?
C17 C19 1.440(4) . ?
C17 C18 1.503(4) . ?
C19 C20 1.369(4) . ?
C20 C21 1.470(4) . ?
C21 C26 1.384(4) . ?
C21 C22 1.390(4) . ?
C22 C23 1.383(5) . ?
C23 C24 1.370(5) . ?
C24 C25 1.372(5) . ?
C25 C26 1.369(4) . ?
C28 C29 1.503(4) . ?
C29 C30 1.498(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653879
