#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/62/4316251.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_4316251
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         'C20 H26 N4 O2'
_chemical_formula_sum            'C20 H26 N4 O2'
_chemical_formula_weight         354.45
_chemical_name_systematic        ?
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 116.165(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0829(4)
_cell_length_b                   30.7570(17)
_cell_length_c                   8.7926(4)
_cell_measurement_reflns_used    18878
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.6
_cell_volume                     1961.90(18)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19156
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.56
_diffrn_reflns_theta_min         2.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0724P)²+0.0412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1090
_reflns_number_gt                3012
_reflns_number_total             3676
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic100754k_si_002_03.cif
_cod_data_source_block           L3Me2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_cell_volume        1961.90(17)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4316251
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.97489(15) 0.64707(3) 0.38667(12) 0.0395(3) Uani 1 1 d . . .
O2 O 0.93577(17) 0.72881(3) 0.92853(13) 0.0475(3) Uani 1 1 d . . .
C1 C 0.89584(17) 0.64759(4) 0.61659(15) 0.0264(3) Uani 1 1 d . . .
C2 C 0.96625(19) 0.66971(4) 0.51735(16) 0.0329(3) Uani 1 1 d . . .
C3 C 1.0254(2) 0.71214(5) 0.55663(19) 0.0414(4) Uani 1 1 d . . .
H3 H 1.0708 0.7271 0.4883 0.050 Uiso 1 1 calc R . .
C4 C 1.0200(2) 0.73342(5) 0.69394(18) 0.0416(4) Uani 1 1 d . . .
H4 H 1.0631 0.7625 0.7203 0.050 Uiso 1 1 calc R . .
C5 C 0.95148(19) 0.71187(4) 0.79138(16) 0.0337(3) Uani 1 1 d . . .
C6 C 0.89092(17) 0.66913(4) 0.75233(15) 0.0281(3) Uani 1 1 d . . .
H6 H 0.8450 0.6544 0.8208 0.034 Uiso 1 1 calc R . .
C7 C 0.9619(3) 0.67115(6) 0.2441(2) 0.0601(5) Uani 1 1 d . . .
H7A H 0.8537 0.6902 0.2045 0.090 Uiso 1 1 calc R . .
H7B H 0.9498 0.6511 0.1532 0.090 Uiso 1 1 calc R . .
H7C H 1.0733 0.6888 0.2763 0.090 Uiso 1 1 calc R . .
C8 C 0.9924(3) 0.77224(5) 0.9728(2) 0.0548(4) Uani 1 1 d . . .
H8A H 1.1212 0.7754 0.9935 0.082 Uiso 1 1 calc R . .
H8B H 0.9806 0.7800 1.0758 0.082 Uiso 1 1 calc R . .
H8C H 0.9146 0.7916 0.8801 0.082 Uiso 1 1 calc R . .
C11 C 0.84062(17) 0.59944(4) 0.58661(14) 0.0253(3) Uani 1 1 d . . .
C12 C 1.00747(19) 0.57222(4) 0.60508(17) 0.0322(3) Uani 1 1 d . . .
H12A H 0.9803 0.5413 0.6089 0.048 Uiso 1 1 calc R . .
H12B H 1.1148 0.5803 0.7100 0.048 Uiso 1 1 calc R . .
H12C H 1.0339 0.5777 0.5082 0.048 Uiso 1 1 calc R . .
N11 N 0.78032(14) 0.58420(3) 0.71334(12) 0.0256(2) Uani 1 1 d . . .
N12 N 0.91262(16) 0.56709(3) 0.86094(13) 0.0311(3) Uani 1 1 d . . .
C13 C 0.8312(2) 0.56287(4) 0.96193(17) 0.0354(3) Uani 1 1 d . . .
C14 C 0.6491(2) 0.57799(4) 0.88313(17) 0.0352(3) Uani 1 1 d . . .
H14 H 0.5632 0.5784 0.9299 0.042 Uiso 1 1 calc R . .
C15 C 0.61941(18) 0.59211(4) 0.72489(16) 0.0291(3) Uani 1 1 d . . .
C16 C 0.9338(3) 0.54407(6) 1.13623(19) 0.0521(4) Uani 1 1 d . . .
H16A H 0.9280 0.5123 1.1295 0.078 Uiso 1 1 calc R . .
H16B H 0.8775 0.5542 1.2083 0.078 Uiso 1 1 calc R . .
H16C H 1.0628 0.5534 1.1847 0.078 Uiso 1 1 calc R . .
C17 C 0.45097(19) 0.61217(5) 0.59075(18) 0.0369(3) Uani 1 1 d . . .
H17A H 0.4840 0.6393 0.5522 0.055 Uiso 1 1 calc R . .
H17B H 0.3628 0.6184 0.6365 0.055 Uiso 1 1 calc R . .
H17C H 0.3950 0.5920 0.4951 0.055 Uiso 1 1 calc R . .
N21 N 0.68509(14) 0.59323(3) 0.41832(12) 0.0262(2) Uani 1 1 d . . .
N22 N 0.59756(15) 0.62860(3) 0.32304(13) 0.0301(3) Uani 1 1 d . . .
C23 C 0.45748(19) 0.61235(5) 0.18681(16) 0.0355(3) Uani 1 1 d . . .
C24 C 0.4537(2) 0.56694(5) 0.19520(17) 0.0380(3) Uani 1 1 d . . .
H24 H 0.3668 0.5480 0.1137 0.046 Uiso 1 1 calc R . .
C25 C 0.59990(19) 0.55523(4) 0.34393(17) 0.0320(3) Uani 1 1 d . . .
C26 C 0.3306(2) 0.64176(6) 0.05010(19) 0.0517(4) Uani 1 1 d . . .
H26A H 0.3261 0.6702 0.0987 0.078 Uiso 1 1 calc R . .
H26B H 0.2068 0.6291 -0.0022 0.078 Uiso 1 1 calc R . .
H26C H 0.3757 0.6454 -0.0359 0.078 Uiso 1 1 calc R . .
C27 C 0.6600(2) 0.51076(5) 0.4151(2) 0.0434(4) Uani 1 1 d . . .
H27A H 0.5607 0.4900 0.3548 0.065 Uiso 1 1 calc R . .
H27B H 0.6890 0.5107 0.5358 0.065 Uiso 1 1 calc R . .
H27C H 0.7698 0.5024 0.4017 0.065 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 117.62(12) . . ?
C5 O2 C8 117.30(13) . . ?
C6 C1 C2 118.48(11) . . ?
C6 C1 C11 119.61(11) . . ?
C2 C1 C11 121.70(11) . . ?
O1 C2 C3 123.34(12) . . ?
O1 C2 C1 117.21(12) . . ?
C3 C2 C1 119.44(13) . . ?
C2 C3 C4 121.48(13) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 119.24(13) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
O2 C5 C4 125.68(12) . . ?
O2 C5 C6 114.66(12) . . ?
C4 C5 C6 119.66(13) . . ?
C1 C6 C5 121.69(12) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
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 107.33(10) . . ?
N21 C11 C12 110.91(10) . . ?
N11 C11 C12 108.33(9) . . ?
N21 C11 C1 110.64(9) . . ?
N11 C11 C1 110.14(10) . . ?
C12 C11 C1 109.43(10) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 N11 N12 111.56(10) . . ?
C15 N11 C11 129.79(10) . . ?
N12 N11 C11 117.20(10) . . ?
C13 N12 N11 105.16(11) . . ?
N12 C13 C14 111.11(12) . . ?
N12 C13 C16 120.59(14) . . ?
C14 C13 C16 128.30(14) . . ?
C15 C14 C13 106.37(12) . . ?
C15 C14 H14 126.8 . . ?
C13 C14 H14 126.8 . . ?
N11 C15 C14 105.75(12) . . ?
N11 C15 C17 125.60(11) . . ?
C14 C15 C17 128.65(13) . . ?
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 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N22 N21 C25 111.85(10) . . ?
N22 N21 C11 119.69(9) . . ?
C25 N21 C11 128.20(11) . . ?
C23 N22 N21 104.95(11) . . ?
N22 C23 C24 110.92(12) . . ?
N22 C23 C26 120.46(14) . . ?
C24 C23 C26 128.61(13) . . ?
C25 C24 C23 106.46(12) . . ?
C25 C24 H24 126.8 . . ?
C23 C24 H24 126.8 . . ?
N21 C25 C24 105.81(12) . . ?
N21 C25 C27 125.45(12) . . ?
C24 C25 C27 128.74(12) . . ?
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 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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 1.3714(17) . ?
O1 C7 1.4192(17) . ?
O2 C5 1.3699(17) . ?
O2 C8 1.4103(17) . ?
C1 C6 1.3809(18) . ?
C1 C2 1.4093(18) . ?
C1 C11 1.5356(17) . ?
C2 C3 1.380(2) . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3920(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 1.4717(15) . ?
C11 N11 1.4757(16) . ?
C11 C12 1.5339(18) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N11 C15 1.3702(17) . ?
N11 N12 1.3715(14) . ?
N12 C13 1.3242(18) . ?
C13 C14 1.401(2) . ?
C13 C16 1.4999(19) . ?
C14 C15 1.3740(19) . ?
C14 H14 0.9500 . ?
C15 C17 1.4863(19) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N21 N22 1.3651(14) . ?
N21 C25 1.3677(16) . ?
N22 C23 1.3306(17) . ?
C23 C24 1.400(2) . ?
C23 C26 1.493(2) . ?
C24 C25 1.369(2) . ?
C24 H24 0.9500 . ?
C25 C27 1.494(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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 -29.4(2) . . . . ?
C7 O1 C2 C1 151.72(14) . . . . ?
C6 C1 C2 O1 177.99(11) . . . . ?
C11 C1 C2 O1 3.22(18) . . . . ?
C6 C1 C2 C3 -0.91(19) . . . . ?
C11 C1 C2 C3 -175.68(12) . . . . ?
O1 C2 C3 C4 -177.75(13) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C8 O2 C5 C4 0.9(2) . . . . ?
C8 O2 C5 C6 -179.07(14) . . . . ?
C3 C4 C5 O2 -179.18(14) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C2 C1 C6 C5 0.71(19) . . . . ?
C11 C1 C6 C5 175.59(12) . . . . ?
O2 C5 C6 C1 179.30(12) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C6 C1 C11 N21 121.06(12) . . . . ?
C2 C1 C11 N21 -64.24(15) . . . . ?
C6 C1 C11 N11 2.55(15) . . . . ?
C2 C1 C11 N11 177.25(11) . . . . ?
C6 C1 C11 C12 -116.44(12) . . . . ?
C2 C1 C11 C12 58.27(15) . . . . ?
N21 C11 N11 C15 -45.84(15) . . . . ?
C12 C11 N11 C15 -165.66(12) . . . . ?
C1 C11 N11 C15 74.68(15) . . . . ?
N21 C11 N11 N12 149.21(10) . . . . ?
C12 C11 N11 N12 29.38(14) . . . . ?
C1 C11 N11 N12 -90.27(12) . . . . ?
C15 N11 N12 C13 2.27(13) . . . . ?
C11 N11 N12 C13 169.88(10) . . . . ?
N11 N12 C13 C14 -1.39(14) . . . . ?
N11 N12 C13 C16 178.83(12) . . . . ?
N12 C13 C14 C15 0.07(15) . . . . ?
C16 C13 C14 C15 179.83(14) . . . . ?
N12 N11 C15 C14 -2.24(13) . . . . ?
C11 N11 C15 C14 -167.86(11) . . . . ?
N12 N11 C15 C17 177.44(12) . . . . ?
C11 N11 C15 C17 11.8(2) . . . . ?
C13 C14 C15 N11 1.29(14) . . . . ?
C13 C14 C15 C17 -178.38(13) . . . . ?
N11 C11 N21 N22 112.29(11) . . . . ?
C12 C11 N21 N22 -129.55(12) . . . . ?
C1 C11 N21 N22 -7.91(15) . . . . ?
N11 C11 N21 C25 -61.44(15) . . . . ?
C12 C11 N21 C25 56.72(16) . . . . ?
C1 C11 N21 C25 178.36(12) . . . . ?
C25 N21 N22 C23 -0.70(14) . . . . ?
C11 N21 N22 C23 -175.40(11) . . . . ?
N21 N22 C23 C24 0.64(15) . . . . ?
N21 N22 C23 C26 -178.90(13) . . . . ?
N22 C23 C24 C25 -0.36(17) . . . . ?
C26 C23 C24 C25 179.13(15) . . . . ?
N22 N21 C25 C24 0.49(15) . . . . ?
C11 N21 C25 C24 174.62(12) . . . . ?
N22 N21 C25 C27 -179.78(12) . . . . ?
C11 N21 C25 C27 -5.6(2) . . . . ?
C23 C24 C25 N21 -0.08(15) . . . . ?
C23 C24 C25 C27 -179.80(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661005
