#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/18/8101895.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_8101895
loop_
_publ_author_name
'Irrgang, T.'
'Karthikeyan, S.'
'Balireddi, S.'
'Kempe, R.'
_publ_section_title
;
Crystal structure of N,N'-bis(2-methyl-4,5-diphenyl-imidazo[1,5-b]
pyridazin-7-yl)-1,3-diaminopropane ethanol solvate, C₃₂H₆(NH)₂
(C₁₉H₁₄N₃)₂ · C₂H₅OH
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              20
_journal_page_last               22
_journal_volume                  221
_journal_year                    2006
_chemical_formula_structural     'C3H6(NH)2(C19H14N3)2 &#x00B7; C2H5OH'
_chemical_formula_sum            'C43 H42 N8 O'
_chemical_formula_weight         686.85
_chemical_name_systematic
;N,N'-bis(2-methyl-4,5-diphenylimidazo[1,5-b]pyridazin-7-yl)-1,3-diaminopropane
 ethanol solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.84(3)
_cell_angle_beta                 105.18(3)
_cell_angle_gamma                93.43(3)
_cell_formula_units_Z            2
_cell_length_a                   9.997(2)
_cell_length_b                   12.046(2)
_cell_length_c                   15.635(3)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      48.65
_cell_measurement_theta_min      2.70
_cell_volume                     1813.0(6)
_computing_data_collection       X-AREA-STOE
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Stoe IPDS II'
_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  0.1433
_diffrn_reflns_av_sigmaI/netI    0.1813
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24191
_diffrn_reflns_theta_full        25.84
_diffrn_reflns_theta_max         25.84
_diffrn_reflns_theta_min         1.35
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.855
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         6857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.855
_refine_ls_R_factor_all          0.1957
_refine_ls_R_factor_gt           0.0703
_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)+(0.0582P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1655
_reflns_number_gt                2637
_reflns_number_total             6857
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1686.cff
_cod_data_source_block           k172a
_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        1813.1(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8101895
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.4189(4) 0.4124(3) 0.3660(3) 0.0421(10) Uani 1 2 i d . . .
C2 C 0.4865(4) 0.3098(3) 0.3996(3) 0.0421(10) Uani 1 2 i d . . .
C3 C 0.6201(5) 0.3178(4) 0.4535(3) 0.0550(12) Uani 1 2 i d . . .
H3 H 0.6668 0.3874 0.4684 0.066 Uiso 1 2 i calc R . .
C4 C 0.6854(5) 0.2228(4) 0.4856(3) 0.0644(14) Uani 1 2 i d . . .
H4 H 0.7748 0.2287 0.5231 0.077 Uiso 1 2 i calc R . .
C5 C 0.6176(6) 0.1199(4) 0.4619(3) 0.0600(13) Uani 1 2 i d . . .
H5 H 0.6620 0.0562 0.4827 0.072 Uiso 1 2 i calc R . .
C6 C 0.4863(5) 0.1105(3) 0.4083(3) 0.0528(12) Uani 1 2 i d . . .
H6 H 0.4411 0.0405 0.3928 0.063 Uiso 1 2 i calc R . .
C7 C 0.4189(5) 0.2051(3) 0.3763(3) 0.0477(11) Uani 1 2 i d . . .
H7 H 0.3290 0.1984 0.3395 0.057 Uiso 1 2 i calc R . .
C8 C 0.2934(4) 0.4502(3) 0.3682(3) 0.0403(10) Uani 1 2 i d . . .
C9 C 0.1786(4) 0.4253(3) 0.4037(3) 0.0424(11) Uani 1 2 i d . . .
C10 C 0.1768(5) 0.3270(3) 0.4614(3) 0.0446(11) Uani 1 2 i d . . .
C11 C 0.2909(5) 0.3049(4) 0.5284(3) 0.0526(12) Uani 1 2 i d . . .
H11 H 0.3698 0.3535 0.5401 0.063 Uiso 1 2 i calc R . .
C12 C 0.2904(5) 0.2116(4) 0.5790(3) 0.0581(13) Uani 1 2 i d . . .
H12 H 0.3686 0.1967 0.6235 0.070 Uiso 1 2 i calc R . .
C13 C 0.1722(6) 0.1410(4) 0.5623(3) 0.0637(14) Uani 1 2 i d . . .
H13 H 0.1712 0.0775 0.5953 0.076 Uiso 1 2 i calc R . .
C14 C 0.0572(6) 0.1636(4) 0.4981(3) 0.0628(14) Uani 1 2 i d . . .
H14 H -0.0228 0.1165 0.4887 0.075 Uiso 1 2 i calc R . .
C15 C 0.0580(5) 0.2560(4) 0.4465(3) 0.0545(12) Uani 1 2 i d . . .
H15 H -0.0207 0.2705 0.4021 0.065 Uiso 1 2 i calc R . .
C16 C 0.0725(5) 0.4933(3) 0.3841(3) 0.0500(12) Uani 1 2 i d . . .
H16 H -0.0031 0.4789 0.4074 0.060 Uiso 1 2 i calc R . .
C17 C 0.0730(5) 0.5869(3) 0.3286(3) 0.0470(11) Uani 1 2 i d . . .
C18 C -0.0492(5) 0.6559(4) 0.3044(3) 0.0662(14) Uani 1 2 i d . . .
H18A H -0.0314 0.7147 0.2672 0.099 Uiso 1 2 i calc R . .
H18B H -0.0654 0.6874 0.3573 0.099 Uiso 1 2 i calc R . .
H18C H -0.1297 0.6103 0.2731 0.099 Uiso 1 2 i calc R . .
C19 C 0.4021(5) 0.5645(3) 0.2936(3) 0.0432(11) Uani 1 2 i d . . .
C20 C 0.5392(5) 0.6555(4) 0.2046(3) 0.0587(13) Uani 1 2 i d . . .
H20A H 0.6227 0.6345 0.2470 0.070 Uiso 1 2 i calc R . .
H20B H 0.5573 0.7305 0.1868 0.070 Uiso 1 2 i calc R . .
C21 C 0.5098(6) 0.5786(4) 0.1249(4) 0.0680(15) Uani 1 2 i d . . .
H21A H 0.4929 0.5035 0.1430 0.082 Uiso 1 2 i calc R . .
H21B H 0.5918 0.5796 0.1027 0.082 Uiso 1 2 i calc R . .
C22 C 0.3865(6) 0.6067(4) 0.0498(3) 0.0656(15) Uani 1 2 i d . . .
H22A H 0.3696 0.5495 0.0032 0.079 Uiso 1 2 i calc R . .
H22B H 0.3043 0.6076 0.0717 0.079 Uiso 1 2 i calc R . .
C23 C 0.3510(5) 0.8067(4) 0.0326(3) 0.0493(12) Uani 1 2 i d . . .
C24 C 0.2490(4) 0.9282(3) 0.0925(3) 0.0405(10) Uani 1 2 i d . . .
C25 C 0.1754(4) 0.9660(3) 0.1563(3) 0.0380(10) Uani 1 2 i d . . .
C26 C 0.2047(5) 0.9247(3) 0.2416(3) 0.0500(12) Uani 1 2 i d . . .
H26 H 0.2733 0.8745 0.2588 0.060 Uiso 1 2 i calc R . .
C27 C 0.1322(5) 0.9580(4) 0.3013(3) 0.0610(13) Uani 1 2 i d . . .
H27 H 0.1530 0.9300 0.3580 0.073 Uiso 1 2 i calc R . .
C28 C 0.0315(5) 1.0308(4) 0.2775(3) 0.0590(13) Uani 1 2 i d . . .
H28 H -0.0155 1.0532 0.3182 0.071 Uiso 1 2 i calc R . .
C29 C -0.0015(5) 1.0717(4) 0.1933(3) 0.0532(12) Uani 1 2 i d . . .
H29 H -0.0711 1.1211 0.1768 0.064 Uiso 1 2 i calc R . .
C30 C 0.0697(4) 1.0389(3) 0.1339(3) 0.0453(11) Uani 1 2 i d . . .
H30 H 0.0463 1.0662 0.0769 0.054 Uiso 1 2 i calc R . .
C31 C 0.2789(4) 0.9799(3) 0.0203(3) 0.0417(10) Uani 1 2 i d . . .
C32 C 0.2682(4) 1.0824(3) -0.0236(3) 0.0435(11) Uani 1 2 i d . . .
C33 C 0.2223(4) 1.1834(3) 0.0125(3) 0.0468(11) Uani 1 2 i d . . .
C34 C 0.2876(5) 1.2249(4) 0.0972(3) 0.0507(12) Uani 1 2 i d . . .
H34 H 0.3606 1.1881 0.1321 0.061 Uiso 1 2 i calc R . .
C35 C 0.2466(6) 1.3200(4) 0.1308(4) 0.0645(14) Uani 1 2 i d . . .
H35 H 0.2926 1.3475 0.1874 0.077 Uiso 1 2 i calc R . .
C36 C 0.1373(7) 1.3737(4) 0.0801(5) 0.0812(17) Uani 1 2 i d . . .
H36 H 0.1085 1.4371 0.1027 0.097 Uiso 1 2 i calc R . .
C37 C 0.0704(6) 1.3338(5) -0.0042(5) 0.0844(18) Uani 1 2 i d . . .
H37 H -0.0041 1.3703 -0.0379 0.101 Uiso 1 2 i calc R . .
C38 C 0.1128(5) 1.2400(4) -0.0395(3) 0.0636(14) Uani 1 2 i d . . .
H38 H 0.0691 1.2149 -0.0971 0.076 Uiso 1 2 i calc R . .
C39 C 0.3057(4) 1.0867(4) -0.1012(3) 0.0513(12) Uani 1 2 i d . . .
H39 H 0.2961 1.1520 -0.1326 0.062 Uiso 1 2 i calc R . .
C40 C 0.3596(4) 0.9935(4) -0.1357(3) 0.0495(12) Uani 1 2 i d . . .
C41 C 0.3981(5) 0.9996(4) -0.2231(3) 0.0722(15) Uani 1 2 i d . . .
H41A H 0.4334 0.9305 -0.2355 0.108 Uiso 1 2 i calc R . .
H41B H 0.4681 1.0590 -0.2195 0.108 Uiso 1 2 i calc R . .
H41C H 0.3174 1.0133 -0.2697 0.108 Uiso 1 2 i calc R . .
C101 C 0.7174(8) 0.3443(4) 0.2298(4) 0.124(3) Uani 1 2 i d . . .
H10A H 0.6300 0.3518 0.1858 0.149 Uiso 1 2 i calc R . .
H10B H 0.7142 0.2728 0.2572 0.149 Uiso 1 2 i calc R . .
O1 O 0.7450(4) 0.4329(4) 0.2944(3) 0.1183(15) Uani 1 2 i d . . .
H1 H 0.6832 0.4318 0.3201 0.177 Uiso 1 2 i calc R . .
N1 N 0.4863(4) 0.4841(3) 0.3200(2) 0.0480(9) Uani 1 2 i d . . .
N2 N 0.1763(4) 0.6163(3) 0.2968(2) 0.0468(9) Uani 1 2 i d . . .
N3 N 0.2847(4) 0.5486(3) 0.3192(2) 0.0419(9) Uani 1 2 i d . . .
N4 N 0.4280(4) 0.6557(3) 0.2479(3) 0.0488(10) Uani 1 2 i d . . .
N5 N 0.4108(5) 0.7152(3) 0.0130(3) 0.0630(12) Uani 1 2 i d . . .
N6 N 0.2976(4) 0.8227(3) 0.1002(2) 0.0448(9) Uani 1 2 i d . . .
N7 N 0.3418(4) 0.8978(3) -0.0180(2) 0.0449(9) Uani 1 2 i d . . .
N8 N 0.3820(4) 0.9001(3) -0.0955(2) 0.0522(10) Uani 1 2 i d . . .
C102 C 0.8411(6) 0.3567(5) 0.1877(4) 0.0940(19) Uani 1 2 i d . . .
H10C H 0.8317 0.2990 0.1431 0.141 Uiso 1 2 i calc R . .
H10D H 0.9264 0.3508 0.2328 0.141 Uiso 1 2 i calc R . .
H10E H 0.8421 0.4280 0.1612 0.141 Uiso 1 2 i calc R . .
H4N H 0.349(5) 0.679(4) 0.221(3) 0.056(15) Uiso 1 2 i d . . .
H5N H 0.392(6) 0.709(5) -0.043(4) 0.10(2) Uiso 1 2 i 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'
H4N H4N 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'
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
C8 C1 N1 110.5(3) . . ?
C8 C1 C2 131.4(4) . . ?
N1 C1 C2 117.9(4) . . ?
C3 C2 C7 119.2(4) . . ?
C3 C2 C1 119.5(4) . . ?
C7 C2 C1 121.3(4) . . ?
C2 C3 C4 120.4(4) . . ?
C5 C4 C3 119.8(5) . . ?
C6 C5 C4 120.5(4) . . ?
C5 C6 C7 120.3(4) . . ?
C2 C7 C6 119.8(4) . . ?
C1 C8 N3 104.0(3) . . ?
C1 C8 C9 141.5(4) . . ?
N3 C8 C9 114.5(4) . . ?
C16 C9 C8 117.6(4) . . ?
C16 C9 C10 121.8(4) . . ?
C8 C9 C10 120.6(4) . . ?
C11 C10 C15 119.0(4) . . ?
C11 C10 C9 121.5(4) . . ?
C15 C10 C9 119.5(4) . . ?
C10 C11 C12 121.1(5) . . ?
C13 C12 C11 119.0(5) . . ?
C14 C13 C12 120.5(5) . . ?
C13 C14 C15 120.6(5) . . ?
C14 C15 C10 119.7(5) . . ?
C9 C16 C17 122.1(4) . . ?
N2 C17 C16 123.2(4) . . ?
N2 C17 C18 116.3(4) . . ?
C16 C17 C18 120.5(4) . . ?
N1 C19 N3 111.5(3) . . ?
N1 C19 N4 126.3(4) . . ?
N3 C19 N4 122.2(4) . . ?
N4 C20 C21 114.0(4) . . ?
C20 C21 C22 114.6(4) . . ?
N5 C22 C21 111.6(4) . . ?
N6 C23 N5 127.5(4) . . ?
N6 C23 N7 110.9(4) . . ?
N5 C23 N7 121.5(4) . . ?
N6 C24 C31 110.2(3) . . ?
N6 C24 C25 118.6(3) . . ?
C31 C24 C25 131.2(4) . . ?
C30 C25 C26 117.1(4) . . ?
C30 C25 C24 122.4(4) . . ?
C26 C25 C24 120.4(4) . . ?
C27 C26 C25 120.5(4) . . ?
C28 C27 C26 120.7(4) . . ?
C27 C28 C29 120.2(4) . . ?
C28 C29 C30 119.4(4) . . ?
C29 C30 C25 122.1(4) . . ?
C24 C31 N7 103.8(3) . . ?
C24 C31 C32 141.5(4) . . ?
N7 C31 C32 114.7(3) . . ?
C39 C32 C31 117.3(4) . . ?
C39 C32 C33 119.7(4) . . ?
C31 C32 C33 123.0(4) . . ?
C34 C33 C38 118.7(4) . . ?
C34 C33 C32 121.0(4) . . ?
C38 C33 C32 120.2(4) . . ?
C35 C34 C33 121.3(5) . . ?
C36 C35 C34 119.6(5) . . ?
C35 C36 C37 120.2(5) . . ?
C36 C37 C38 120.8(5) . . ?
C37 C38 C33 119.4(5) . . ?
C32 C39 C40 121.8(4) . . ?
N8 C40 C39 124.0(4) . . ?
N8 C40 C41 115.2(4) . . ?
C39 C40 C41 120.8(4) . . ?
O1 C101 C102 103.6(4) . . ?
C19 N1 C1 106.0(3) . . ?
C17 N2 N3 114.1(3) . . ?
C19 N3 N2 123.7(3) . . ?
C19 N3 C8 108.0(3) . . ?
N2 N3 C8 128.3(3) . . ?
C19 N4 C20 119.1(4) . . ?
C23 N5 C22 121.7(4) . . ?
C23 N6 C24 106.6(3) . . ?
C23 N7 N8 122.5(4) . . ?
C23 N7 C31 108.4(3) . . ?
N8 N7 C31 129.0(3) . . ?
C40 N8 N7 112.9(4) . . ?
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
C1 C8 1.369(5) . ?
C1 N1 1.385(5) . ?
C1 C2 1.480(6) . ?
C2 C3 1.377(6) . ?
C2 C7 1.391(5) . ?
C3 C4 1.387(6) . ?
C4 C5 1.374(6) . ?
C5 C6 1.357(6) . ?
C6 C7 1.391(6) . ?
C8 N3 1.414(5) . ?
C8 C9 1.419(5) . ?
C9 C16 1.354(6) . ?
C9 C10 1.501(5) . ?
C10 C11 1.375(6) . ?
C10 C15 1.386(6) . ?
C11 C12 1.384(6) . ?
C12 C13 1.378(6) . ?
C13 C14 1.358(7) . ?
C14 C15 1.386(6) . ?
C16 C17 1.433(6) . ?
C17 N2 1.293(5) . ?
C17 C18 1.489(6) . ?
C19 N1 1.321(5) . ?
C19 N3 1.340(5) . ?
C19 N4 1.367(5) . ?
C20 N4 1.444(5) . ?
C20 C21 1.497(6) . ?
C21 C22 1.522(7) . ?
C22 N5 1.469(5) . ?
C23 N6 1.320(5) . ?
C23 N5 1.354(6) . ?
C23 N7 1.355(5) . ?
C24 N6 1.383(5) . ?
C24 C31 1.388(5) . ?
C24 C25 1.467(5) . ?
C25 C30 1.392(6) . ?
C25 C26 1.395(5) . ?
C26 C27 1.390(6) . ?
C27 C28 1.358(6) . ?
C28 C29 1.377(6) . ?
C29 C30 1.377(5) . ?
C31 N7 1.408(5) . ?
C31 C32 1.418(5) . ?
C32 C39 1.362(5) . ?
C32 C33 1.480(6) . ?
C33 C34 1.385(6) . ?
C33 C38 1.401(6) . ?
C34 C35 1.381(6) . ?
C35 C36 1.373(7) . ?
C36 C37 1.377(8) . ?
C37 C38 1.387(7) . ?
C39 C40 1.432(6) . ?
C40 N8 1.299(5) . ?
C40 C41 1.515(5) . ?
C101 O1 1.423(6) . ?
C101 C102 1.547(7) . ?
N2 N3 1.371(4) . ?
N7 N8 1.373(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653891
