#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/18/8101898.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_8101898
loop_
_publ_author_name
'Irrgang, T.'
'Balireddi, S.'
'Karthikeyan, S.'
'Kempe, R.'
_publ_section_title
;
Crystal structure of N,N'-bis(2-methyl-4-phenyl-5-tert-butylimidazo
[1,5-b]pyridazin-7-yl)ethylenediamine, C₂H₄(NH)₂(C₁₇H₁₈N₃)
₂
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              23
_journal_page_last               24
_journal_volume                  221
_journal_year                    2006
_chemical_formula_sum            'C36 H42 N8'
_chemical_formula_weight         586.78
_chemical_name_systematic
;
N,N'-bis(2-methyl-4-phenyl-5-tert-butylimidazo[1,5-b]pyridazin-
7-yl)ethylenediamine
;
_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                 109.30(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.004(3)
_cell_length_b                   9.1644(18)
_cell_length_c                   13.468(3)
_cell_measurement_reflns_used    20975
_cell_measurement_temperature    193(2)
_cell_volume                     1631.3(7)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       phi
_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  0.1258
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20975
_diffrn_reflns_theta_full        25.83
_diffrn_reflns_theta_max         25.83
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0601
_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)+(0.0612P)²+0.4325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1580
_reflns_number_gt                2204
_reflns_number_total             3103
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1689.cff
_cod_data_source_block           k169m
_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        1631.3(6)
_cod_original_sg_symbol_H-M      P12(1)/c1
_cod_database_code               8101898
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_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 0.79166(17) 0.1519(2) 0.35218(17) 0.0453(5) Uani 1 4 e d . . .
C2 C 0.67710(18) 0.1615(3) 0.31986(19) 0.0511(6) Uani 1 4 e d . . .
C3 C 0.6338(2) 0.0214(4) 0.3472(4) 0.0995(13) Uani 1 4 e d . . .
H3A H 0.6491 -0.0598 0.3075 0.149 Uiso 1 4 e calc R . .
H3B H 0.5603 0.0311 0.3290 0.149 Uiso 1 4 e calc R . .
H3C H 0.6640 0.0023 0.4227 0.149 Uiso 1 4 e calc R . .
C4 C 0.6302(2) 0.1951(5) 0.2032(2) 0.0914(11) Uani 1 4 e d . . .
H4A H 0.6444 0.1148 0.1620 0.137 Uiso 1 4 e calc R . .
H4B H 0.6590 0.2857 0.1869 0.137 Uiso 1 4 e calc R . .
H4C H 0.5568 0.2063 0.1854 0.137 Uiso 1 4 e calc R . .
C5 C 0.6483(2) 0.2863(4) 0.3792(3) 0.0870(10) Uani 1 4 e d . . .
H5A H 0.5744 0.2941 0.3574 0.130 Uiso 1 4 e calc R . .
H5B H 0.6765 0.3778 0.3635 0.130 Uiso 1 4 e calc R . .
H5C H 0.6754 0.2672 0.4550 0.130 Uiso 1 4 e calc R . .
C6 C 0.85652(16) 0.0546(2) 0.32659(17) 0.0427(5) Uani 1 4 e d . . .
C7 C 0.85849(17) -0.0703(2) 0.26404(17) 0.0452(5) Uani 1 4 e d . . .
C8 C 0.76677(18) -0.1431(3) 0.19202(19) 0.0494(6) Uani 1 4 e d . . .
C9 C 0.7265(2) -0.2646(3) 0.2233(2) 0.0662(7) Uani 1 4 e d . . .
H9 H 0.7558 -0.3006 0.2930 0.079 Uiso 1 4 e calc R . .
C10 C 0.6435(2) -0.3348(3) 0.1540(3) 0.0807(10) Uani 1 4 e d . . .
H10 H 0.6160 -0.4183 0.1765 0.097 Uiso 1 4 e calc R . .
C11 C 0.6009(2) -0.2846(4) 0.0535(3) 0.0836(10) Uani 1 4 e d . . .
H11 H 0.5433 -0.3320 0.0065 0.100 Uiso 1 4 e calc R . .
C12 C 0.6415(3) -0.1658(4) 0.0209(3) 0.0932(11) Uani 1 4 e d . . .
H12 H 0.6126 -0.1312 -0.0491 0.112 Uiso 1 4 e calc R . .
C13 C 0.7243(2) -0.0962(4) 0.0896(2) 0.0735(8) Uani 1 4 e d . . .
H13 H 0.7526 -0.0145 0.0659 0.088 Uiso 1 4 e calc R . .
C14 C 0.95035(18) -0.1253(3) 0.26940(18) 0.0489(6) Uani 1 4 e d . . .
H14 H 0.9523 -0.2093 0.2288 0.059 Uiso 1 4 e calc R . .
C15 C 1.04346(18) -0.0630(3) 0.33285(18) 0.0475(6) Uani 1 4 e d . . .
C16 C 1.14228(19) -0.1271(3) 0.3369(2) 0.0575(6) Uani 1 4 e d . . .
H16A H 1.1975 -0.0695 0.3845 0.086 Uiso 1 4 e calc R . .
H16B H 1.1478 -0.1263 0.2662 0.086 Uiso 1 4 e calc R . .
H16C H 1.1466 -0.2278 0.3625 0.086 Uiso 1 4 e calc R . .
C17 C 0.94376(17) 0.2270(2) 0.43736(17) 0.0447(5) Uani 1 4 e d . . .
C18 C 1.01362(19) 0.4411(3) 0.54205(18) 0.0527(6) Uani 1 4 e d . . .
H18A H 1.0774 0.4685 0.5977 0.063 Uiso 1 4 e calc R . .
H18B H 0.9598 0.4355 0.5746 0.063 Uiso 1 4 e calc R . .
N1 N 0.84770(15) 0.2573(2) 0.41978(15) 0.0484(5) Uani 1 4 e d . . .
N2 N 0.95439(14) 0.1072(2) 0.38384(14) 0.0432(5) Uani 1 4 e d . . .
N3 N 1.04764(14) 0.0533(2) 0.39024(14) 0.0452(5) Uani 1 4 e d . . .
N4 N 1.02590(17) 0.2990(2) 0.50123(17) 0.0541(5) Uani 1 4 e d . . .
H4N H 1.085(2) 0.274(3) 0.498(2) 0.057(8) 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
N1 C1 C6 109.6(2) . . ?
N1 C1 C2 117.69(19) . . ?
C6 C1 C2 132.7(2) . . ?
C3 C2 C1 110.5(2) . . ?
C3 C2 C4 110.6(3) . . ?
C1 C2 C4 111.2(2) . . ?
C3 C2 C5 108.2(3) . . ?
C1 C2 C5 109.3(2) . . ?
C4 C2 C5 106.9(3) . . ?
C1 C6 N2 103.87(18) . . ?
C1 C6 C7 143.1(2) . . ?
N2 C6 C7 112.97(19) . . ?
C14 C7 C6 117.9(2) . . ?
C14 C7 C8 117.8(2) . . ?
C6 C7 C8 124.3(2) . . ?
C9 C8 C13 118.3(2) . . ?
C9 C8 C7 121.1(2) . . ?
C13 C8 C7 120.5(2) . . ?
C8 C9 C10 120.4(3) . . ?
C11 C10 C9 120.4(3) . . ?
C12 C11 C10 119.6(3) . . ?
C11 C12 C13 120.1(3) . . ?
C12 C13 C8 121.1(3) . . ?
C7 C14 C15 123.1(2) . . ?
N3 C15 C14 122.4(2) . . ?
N3 C15 C16 116.2(2) . . ?
C14 C15 C16 121.4(2) . . ?
N1 C17 N2 111.26(19) . . ?
N1 C17 N4 127.8(2) . . ?
N2 C17 N4 120.9(2) . . ?
N4 C18 C18 112.9(2) . 3_766 ?
C17 N1 C1 107.17(19) . . ?
C17 N2 N3 122.02(18) . . ?
C17 N2 C6 108.07(18) . . ?
N3 N2 C6 129.90(18) . . ?
C15 N3 N2 113.62(18) . . ?
C17 N4 C18 119.7(2) . . ?
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 N1 1.381(3) . ?
C1 C6 1.395(3) . ?
C1 C2 1.520(3) . ?
C2 C3 1.516(4) . ?
C2 C4 1.521(4) . ?
C2 C5 1.525(4) . ?
C6 N2 1.417(3) . ?
C6 C7 1.427(3) . ?
C7 C14 1.361(3) . ?
C7 C8 1.487(3) . ?
C8 C9 1.376(4) . ?
C8 C13 1.378(4) . ?
C9 C10 1.385(4) . ?
C10 C11 1.366(5) . ?
C11 C12 1.365(5) . ?
C12 C13 1.378(4) . ?
C14 C15 1.421(3) . ?
C15 N3 1.307(3) . ?
C15 C16 1.488(3) . ?
C17 N1 1.316(3) . ?
C17 N2 1.348(3) . ?
C17 N4 1.358(3) . ?
C18 N4 1.446(3) . ?
C18 C18 1.520(5) 3_766 ?
N2 N3 1.372(2) . ?
