#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/62/4316253.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_4316253
loop_
_publ_author_name
'Florian Blasberg'
'Jan W. Bats'
'Michael Bolte'
'Hans-Wolfram Lerner'
'Matthias Wagner'
_publ_contact_author
;
      Dr. Michael Bolte
      Institut für Anorganische Chemie
      J. W. Goethe-Universität
      Max-von-Laue-Str. 7
      60438 Frankfurt/Main
      Germany
;
_publ_contact_author_email       bolte@chemie.uni-frankfurt.de
_publ_contact_author_fax         '49 69 798 29239'
_publ_contact_author_phone       '49 69 798 29136'
_publ_section_title
;
 Para-Quinone-Containing Bis(pyrazol-1-yl)methane Ligands: Coordination
 Behavior Toward CoII and a C-H Activation Reaction with CeIV
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7435
_journal_page_last               7445
_journal_paper_doi               10.1021/ic100754k
_journal_volume                  49
_journal_year                    2010
_chemical_formula_moiety         'C17 H20 N4 O2'
_chemical_formula_sum            'C17 H20 N4 O2'
_chemical_formula_weight         312.37
_chemical_name_systematic        ?
_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                105.627(7)
_cell_angle_beta                 97.151(8)
_cell_angle_gamma                116.804(7)
_cell_formula_units_Z            2
_cell_length_a                   8.7896(8)
_cell_length_b                   9.5608(9)
_cell_length_c                   11.7126(11)
_cell_measurement_reflns_used    6455
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      3.7
_cell_volume                     810.67(16)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7150
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.58
_diffrn_reflns_theta_min         3.70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.057(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.0507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                2469
_reflns_number_total             3022
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic100754k_si_002_05.cif
_cod_data_source_block           L2Me
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4316253
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21758(14) 0.69084(13) 0.49403(9) 0.0348(3) Uani 1 1 d . . .
O2 O 0.45053(14) 0.98157(12) 0.15617(9) 0.0331(3) Uani 1 1 d . . .
C1 C 0.35134(17) 0.71206(15) 0.33414(11) 0.0225(3) Uani 1 1 d . . .
C2 C 0.27787(17) 0.77786(16) 0.41833(12) 0.0254(3) Uani 1 1 d . . .
C3 C 0.26882(18) 0.91853(17) 0.41774(13) 0.0292(3) Uani 1 1 d . . .
H3 H 0.2232 0.9657 0.4765 0.035 Uiso 1 1 calc R . .
C4 C 0.32609(18) 0.99155(17) 0.33169(13) 0.0281(3) Uani 1 1 d . . .
H4 H 0.3184 1.0874 0.3313 0.034 Uiso 1 1 calc R . .
C5 C 0.39418(18) 0.92397(16) 0.24690(12) 0.0252(3) Uani 1 1 d . . .
C6 C 0.40928(18) 0.78609(16) 0.25015(11) 0.0240(3) Uani 1 1 d . . .
H6 H 0.4601 0.7425 0.1938 0.029 Uiso 1 1 calc R . .
C7 C 0.1557(2) 0.7582(2) 0.58946(13) 0.0363(4) Uani 1 1 d . . .
H7A H 0.2521 0.8704 0.6452 0.054 Uiso 1 1 calc R . .
H7B H 0.1172 0.6838 0.6363 0.054 Uiso 1 1 calc R . .
H7C H 0.0553 0.7665 0.5524 0.054 Uiso 1 1 calc R . .
C8 C 0.4527(2) 1.13189(18) 0.15567(14) 0.0374(4) Uani 1 1 d . . .
H8A H 0.3320 1.1137 0.1451 0.056 Uiso 1 1 calc R . .
H8B H 0.4960 1.1604 0.0873 0.056 Uiso 1 1 calc R . .
H8C H 0.5315 1.2245 0.2343 0.056 Uiso 1 1 calc R . .
C11 C 0.36122(17) 0.55961(16) 0.33870(11) 0.0228(3) Uani 1 1 d . . .
H11 H 0.3714 0.5636 0.4257 0.027 Uiso 1 1 calc R . .
N11 N 0.19745(14) 0.40529(13) 0.25983(10) 0.0230(3) Uani 1 1 d . . .
N12 N 0.15650(15) 0.25804(13) 0.27619(11) 0.0274(3) Uani 1 1 d . . .
C13 C 0.00493(19) 0.14285(17) 0.18818(13) 0.0297(3) Uani 1 1 d . . .
C14 C -0.05077(19) 0.21583(18) 0.11632(13) 0.0329(3) Uani 1 1 d . . .
H14 H -0.1547 0.1606 0.0486 0.039 Uiso 1 1 calc R . .
C15 C 0.07566(19) 0.38306(17) 0.16402(12) 0.0288(3) Uani 1 1 d . . .
H15 H 0.0774 0.4675 0.1352 0.035 Uiso 1 1 calc R . .
C16 C -0.0867(2) -0.03856(18) 0.17604(16) 0.0444(4) Uani 1 1 d . . .
H16A H -0.0702 -0.1052 0.1041 0.067 Uiso 1 1 calc R . .
H16B H -0.2140 -0.0809 0.1651 0.067 Uiso 1 1 calc R . .
H16C H -0.0356 -0.0480 0.2509 0.067 Uiso 1 1 calc R . .
N21 N 0.51445(14) 0.55643(13) 0.30723(9) 0.0224(3) Uani 1 1 d . . .
N22 N 0.52109(15) 0.51610(13) 0.18816(9) 0.0242(3) Uani 1 1 d . . .
C23 C 0.68486(18) 0.54331(16) 0.19552(12) 0.0236(3) Uani 1 1 d . . .
C24 C 0.78261(19) 0.60102(18) 0.31857(13) 0.0318(3) Uani 1 1 d . . .
H24 H 0.9021 0.6286 0.3480 0.038 Uiso 1 1 calc R . .
C25 C 0.67081(18) 0.60953(17) 0.38746(12) 0.0287(3) Uani 1 1 d . . .
H25 H 0.6977 0.6458 0.4750 0.034 Uiso 1 1 calc R . .
C26 C 0.7429(2) 0.51071(19) 0.08145(13) 0.0320(3) Uani 1 1 d . . .
H26A H 0.7299 0.3986 0.0564 0.048 Uiso 1 1 calc R . .
H26B H 0.8678 0.5960 0.0984 0.048 Uiso 1 1 calc R . .
H26C H 0.6691 0.5162 0.0148 0.048 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'
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
C2 O1 C7 118.19(11) . . ?
C5 O2 C8 117.21(11) . . ?
C6 C1 C2 119.50(12) . . ?
C6 C1 C11 122.52(11) . . ?
C2 C1 C11 117.97(11) . . ?
O1 C2 C3 125.68(12) . . ?
O1 C2 C1 114.82(12) . . ?
C3 C2 C1 119.49(12) . . ?
C2 C3 C4 120.59(12) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.77(12) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
O2 C5 C4 125.26(12) . . ?
O2 C5 C6 115.01(11) . . ?
C4 C5 C6 119.73(12) . . ?
C1 C6 C5 120.85(12) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N21 C11 N11 110.56(10) . . ?
N21 C11 C1 113.59(10) . . ?
N11 C11 C1 110.33(10) . . ?
N21 C11 H11 107.4 . . ?
N11 C11 H11 107.4 . . ?
C1 C11 H11 107.4 . . ?
C15 N11 N12 111.87(11) . . ?
C15 N11 C11 128.33(11) . . ?
N12 N11 C11 119.74(10) . . ?
C13 N12 N11 104.68(11) . . ?
N12 C13 C14 111.05(12) . . ?
N12 C13 C16 121.23(13) . . ?
C14 C13 C16 127.72(14) . . ?
C15 C14 C13 105.57(13) . . ?
C15 C14 H14 127.2 . . ?
C13 C14 H14 127.2 . . ?
N11 C15 C14 106.83(12) . . ?
N11 C15 H15 126.6 . . ?
C14 C15 H15 126.6 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C25 N21 N22 111.77(11) . . ?
C25 N21 C11 126.44(11) . . ?
N22 N21 C11 121.35(10) . . ?
C23 N22 N21 104.84(10) . . ?
N22 C23 C24 110.94(12) . . ?
N22 C23 C26 120.76(12) . . ?
C24 C23 C26 128.29(13) . . ?
C25 C24 C23 105.68(12) . . ?
C25 C24 H24 127.2 . . ?
C23 C24 H24 127.2 . . ?
N21 C25 C24 106.76(12) . . ?
N21 C25 H25 126.6 . . ?
C24 C25 H25 126.6 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
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
O1 C2 1.3697(16) . ?
O1 C7 1.4281(16) . ?
O2 C5 1.3705(16) . ?
O2 C8 1.4305(16) . ?
C1 C6 1.3794(18) . ?
C1 C2 1.4056(18) . ?
C1 C11 1.5133(17) . ?
C2 C3 1.3843(19) . ?
C3 C4 1.395(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3831(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3929(18) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C11 N21 1.4510(16) . ?
C11 N11 1.4565(17) . ?
C11 H11 1.0000 . ?
N11 C15 1.3482(17) . ?
N11 N12 1.3615(14) . ?
N12 C13 1.3317(18) . ?
C13 C14 1.399(2) . ?
C13 C16 1.5020(19) . ?
C14 C15 1.366(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N21 C25 1.3497(17) . ?
N21 N22 1.3594(14) . ?
N22 C23 1.3291(17) . ?
C23 C24 1.3984(19) . ?
C23 C26 1.4938(18) . ?
C24 C25 1.363(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O1 C2 C3 -6.7(2) . . . . ?
C7 O1 C2 C1 174.51(12) . . . . ?
C6 C1 C2 O1 177.32(11) . . . . ?
C11 C1 C2 O1 -1.89(17) . . . . ?
C6 C1 C2 C3 -1.6(2) . . . . ?
C11 C1 C2 C3 179.20(11) . . . . ?
O1 C2 C3 C4 -176.53(13) . . . . ?
C1 C2 C3 C4 2.3(2) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C8 O2 C5 C4 5.4(2) . . . . ?
C8 O2 C5 C6 -174.60(12) . . . . ?
C3 C4 C5 O2 178.32(12) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C11 C1 C6 C5 178.49(11) . . . . ?
O2 C5 C6 C1 -177.66(11) . . . . ?
C4 C5 C6 C1 2.3(2) . . . . ?
C6 C1 C11 N21 33.79(17) . . . . ?
C2 C1 C11 N21 -147.03(11) . . . . ?
C6 C1 C11 N11 -90.99(14) . . . . ?
C2 C1 C11 N11 88.18(14) . . . . ?
N21 C11 N11 C15 -105.02(14) . . . . ?
C1 C11 N11 C15 21.48(17) . . . . ?
N21 C11 N11 N12 72.06(13) . . . . ?
C1 C11 N11 N12 -161.44(10) . . . . ?
C15 N11 N12 C13 -0.29(14) . . . . ?
C11 N11 N12 C13 -177.83(11) . . . . ?
N11 N12 C13 C14 -0.12(15) . . . . ?
N11 N12 C13 C16 -179.12(12) . . . . ?
N12 C13 C14 C15 0.47(16) . . . . ?
C16 C13 C14 C15 179.39(14) . . . . ?
N12 N11 C15 C14 0.59(15) . . . . ?
C11 N11 C15 C14 177.86(12) . . . . ?
C13 C14 C15 N11 -0.62(15) . . . . ?
N11 C11 N21 C25 -138.86(12) . . . . ?
C1 C11 N21 C25 96.48(14) . . . . ?
N11 C11 N21 N22 49.41(14) . . . . ?
C1 C11 N21 N22 -75.26(14) . . . . ?
C25 N21 N22 C23 0.71(14) . . . . ?
C11 N21 N22 C23 173.55(10) . . . . ?s
N21 N22 C23 C24 -0.11(14) . . . . ?
N21 N22 C23 C26 179.29(11) . . . . ?
N22 C23 C24 C25 -0.50(15) . . . . ?
C26 C23 C24 C25 -179.84(13) . . . . ?
N22 N21 C25 C24 -1.03(15) . . . . ?
C11 N21 C25 C24 -173.43(11) . . . . ?
C23 C24 C25 N21 0.90(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661006
