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#$Date: 2016-03-26 00:38:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180089 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/35/7053553.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_7053553
loop_
_publ_author_name
'Kutlescha, Kathrin'
'Irrgang, Torsten'
'Kempe, Rhett'
_publ_section_title
;
 An intermolecular C--C coupling reaction of iridium complexes
;
_journal_issue                   9
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1954
_journal_paper_doi               10.1039/c0nj00158a
_journal_volume                  34
_journal_year                    2010
_chemical_formula_sum            'C20 H19 N5'
_chemical_formula_weight         329.40
_chemical_name_systematic
;
 ?
;
_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                 92.241(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2845(5)
_cell_length_b                   13.4530(8)
_cell_length_c                   17.5656(14)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      52.10
_cell_measurement_theta_min      3.30
_cell_volume                     1720.1(2)
_computing_cell_refinement       X-AREA-STOE
_computing_data_collection       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  STOE-IPDSII
_diffrn_measurement_method       Omega-Scan
_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  0.0689
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13916
_diffrn_reflns_theta_full        25.85
_diffrn_reflns_theta_max         25.85
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_correction_T_min  0.9691
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.854
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.854
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0391
_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)+(0.0460P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0879
_reflns_number_gt                1989
_reflns_number_total             3256
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0nj00158a.txt
_cod_data_source_block           ti76
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7053553
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_calc_flag
_atom_site_refinement_flags
N1 N 0.28947(19) -0.13255(9) 0.54088(7) 0.0255(3) Uani 1 1 d .
N2 N 0.27977(19) -0.03169(8) 0.52959(7) 0.0222(3) Uani 1 1 d .
N3 N 0.21543(19) 0.10889(9) 0.46912(7) 0.0245(3) Uani 1 1 d .
N4 N 0.1454(2) -0.04516(9) 0.40527(7) 0.0282(3) Uani 1 1 d .
H4 H 0.1471 -0.1104 0.4086 0.034 Uiso 1 1 calc R
N5 N 0.0198(2) -0.17008(10) 0.29980(8) 0.0360(4) Uani 1 1 d .
C1 C 0.2077(2) 0.01101(10) 0.46537(8) 0.0226(3) Uani 1 1 d .
C2 C 0.3633(2) -0.15784(12) 0.60699(9) 0.0276(4) Uani 1 1 d .
C3 C 0.4233(2) -0.08713(12) 0.66411(9) 0.0281(4) Uani 1 1 d .
H3 H 0.4706 -0.1109 0.7119 0.034 Uiso 1 1 calc R
C4 C 0.4146(2) 0.01258(12) 0.65191(8) 0.0248(4) Uani 1 1 d .
C5 C 0.3415(2) 0.04520(11) 0.57944(8) 0.0228(3) Uani 1 1 d .
C6 C 0.2997(2) 0.13131(10) 0.53953(8) 0.0243(4) Uani 1 1 d .
C7 C 0.3837(3) -0.26746(12) 0.62068(11) 0.0393(5) Uani 1 1 d .
H7A H 0.3219 -0.3040 0.5788 0.059 Uiso 1 1 calc R
H7B H 0.3282 -0.2850 0.6688 0.059 Uiso 1 1 calc R
H7C H 0.5144 -0.2849 0.6234 0.059 Uiso 1 1 calc R
C8 C 0.4769(3) 0.08601(13) 0.71220(9) 0.0325(4) Uani 1 1 d .
H8A H 0.4976 0.0514 0.7609 0.049 Uiso 1 1 calc R
H8B H 0.3822 0.1370 0.7176 0.049 Uiso 1 1 calc R
H8C H 0.5915 0.1175 0.6974 0.049 Uiso 1 1 calc R
C9 C 0.3253(3) 0.23698(11) 0.56034(9) 0.0312(4) Uani 1 1 d .
C10 C 0.4919(3) 0.27393(14) 0.59001(10) 0.0448(5) Uani 1 1 d .
H10 H 0.5928 0.2303 0.5991 0.054 Uiso 1 1 calc R
C11 C 0.5105(4) 0.37469(16) 0.60632(12) 0.0699(8) Uani 1 1 d .
H11 H 0.6238 0.3994 0.6272 0.084 Uiso 1 1 calc R
C12 C 0.3664(5) 0.43877(16) 0.59247(13) 0.0841(10) Uani 1 1 d .
H12 H 0.3801 0.5075 0.6036 0.101 Uiso 1 1 calc R
C13 C 0.2016(4) 0.40301(15) 0.56234(11) 0.0718(9) Uani 1 1 d .
H13 H 0.1022 0.4475 0.5525 0.086 Uiso 1 1 calc R
C14 C 0.1800(3) 0.30268(13) 0.54635(9) 0.0466(5) Uani 1 1 d .
H14 H 0.0659 0.2787 0.5258 0.056 Uiso 1 1 calc R
C15 C 0.0768(2) 0.00206(11) 0.33619(8) 0.0244(3) Uani 1 1 d .
H15A H 0.1747 0.0434 0.3149 0.029 Uiso 1 1 calc R
H15B H -0.0274 0.0461 0.3477 0.029 Uiso 1 1 calc R
C16 C 0.0142(2) -0.07522(11) 0.27827(8) 0.0236(4) Uani 1 1 d .
C17 C -0.0468(3) -0.04625(12) 0.20598(9) 0.0335(4) Uani 1 1 d .
H17 H -0.0503 0.0221 0.1925 0.040 Uiso 1 1 calc R
C18 C -0.1027(3) -0.11806(13) 0.15369(9) 0.0386(5) Uani 1 1 d .
H18 H -0.1442 -0.0995 0.1037 0.046 Uiso 1 1 calc R
C19 C -0.0977(3) -0.21634(13) 0.17462(10) 0.0390(5) Uani 1 1 d .
H19 H -0.1342 -0.2673 0.1398 0.047 Uiso 1 1 calc R
C20 C -0.0377(3) -0.23840(13) 0.24797(11) 0.0445(5) Uani 1 1 d .
H20 H -0.0368 -0.3062 0.2631 0.053 Uiso 1 1 calc R
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
C2 N1 N2 113.78(12)
C1 N2 N1 123.79(12)
C1 N2 C5 107.97(12)
N1 N2 C5 128.24(12)
C1 N3 C6 106.08(12)
C1 N4 C15 120.15(12)
C16 N5 C20 117.13(14)
N3 C1 N2 111.57(13)
N3 C1 N4 127.21(13)
N2 C1 N4 121.15(12)
N1 C2 C3 123.48(14)
N1 C2 C7 115.69(14)
C3 C2 C7 120.83(14)
C4 C3 C2 122.11(14)
C3 C4 C5 117.17(14)
C3 C4 C8 121.71(14)
C5 C4 C8 121.11(14)
C6 C5 N2 103.90(12)
C6 C5 C4 140.90(14)
N2 C5 C4 115.11(13)
C5 C6 N3 110.47(12)
C5 C6 C9 131.14(14)
N3 C6 C9 118.36(13)
C14 C9 C10 118.94(16)
C14 C9 C6 118.65(17)
C10 C9 C6 122.34(17)
C11 C10 C9 120.1(2)
C12 C11 C10 120.5(2)
C11 C12 C13 119.8(2)
C12 C13 C14 120.5(2)
C13 C14 C9 120.2(2)
N4 C15 C16 110.42(12)
N5 C16 C17 122.39(14)
N5 C16 C15 117.56(13)
C17 C16 C15 120.06(14)
C18 C17 C16 119.20(15)
C19 C18 C17 119.39(16)
C18 C19 C20 117.56(15)
N5 C20 C19 124.31(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.305(2)
N1 N2 1.3726(17)
N2 C1 1.3534(19)
N2 C5 1.4171(18)
N3 C1 1.3195(19)
N3 C6 1.3923(19)
N4 C1 1.3615(19)
N4 C15 1.4418(19)
N5 C16 1.331(2)
N5 C20 1.349(2)
C2 C3 1.438(2)
C2 C7 1.501(2)
C3 C4 1.360(2)
C4 C5 1.430(2)
C4 C8 1.505(2)
C5 C6 1.382(2)
C6 C9 1.478(2)
C9 C14 1.393(3)
C9 C10 1.394(3)
C10 C11 1.391(3)
C11 C12 1.373(4)
C12 C13 1.379(4)
C13 C14 1.386(3)
C15 C16 1.513(2)
C16 C17 1.385(2)
C17 C18 1.383(2)
C18 C19 1.372(2)
C19 C20 1.376(3)
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
C2 N1 N2 C1 -179.69(15)
C2 N1 N2 C5 1.1(2)
C6 N3 C1 N2 0.83(19)
C6 N3 C1 N4 -176.18(16)
N1 N2 C1 N3 -179.91(14)
C5 N2 C1 N3 -0.56(18)
N1 N2 C1 N4 -2.7(2)
C5 N2 C1 N4 176.66(15)
C15 N4 C1 N3 -0.5(3)
C15 N4 C1 N2 -177.24(15)
N2 N1 C2 C3 2.1(2)
N2 N1 C2 C7 -177.64(14)
N1 C2 C3 C4 -2.9(3)
C7 C2 C3 C4 176.78(17)
C2 C3 C4 C5 0.4(3)
C2 C3 C4 C8 179.69(16)
C1 N2 C5 C6 0.04(16)
N1 N2 C5 C6 179.34(15)
C1 N2 C5 C4 177.35(14)
N1 N2 C5 C4 -3.3(2)
C3 C4 C5 C6 178.2(2)
C8 C4 C5 C6 -1.1(3)
C3 C4 C5 N2 2.3(2)
C8 C4 C5 N2 -176.98(15)
N2 C5 C6 N3 0.47(17)
C4 C5 C6 N3 -175.7(2)
N2 C5 C6 C9 178.62(18)
C4 C5 C6 C9 2.5(4)
C1 N3 C6 C5 -0.81(19)
C1 N3 C6 C9 -179.22(15)
C5 C6 C9 C14 -133.70(19)
N3 C6 C9 C14 44.3(2)
C5 C6 C9 C10 49.4(3)
N3 C6 C9 C10 -132.55(17)
C14 C9 C10 C11 1.0(3)
C6 C9 C10 C11 177.87(17)
C9 C10 C11 C12 -0.9(3)
C10 C11 C12 C13 0.2(4)
C11 C12 C13 C14 0.4(4)
C12 C13 C14 C9 -0.3(3)
C10 C9 C14 C13 -0.4(3)
C6 C9 C14 C13 -177.43(17)
C1 N4 C15 C16 -179.45(14)
C20 N5 C16 C17 -0.3(3)
C20 N5 C16 C15 179.46(17)
N4 C15 C16 N5 4.0(2)
N4 C15 C16 C17 -176.19(16)
N5 C16 C17 C18 -0.6(3)
C15 C16 C17 C18 179.69(17)
C16 C17 C18 C19 0.4(3)
C17 C18 C19 C20 0.6(3)
C16 N5 C20 C19 1.4(3)
C18 C19 C20 N5 -1.5(3)
