#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/62/4316257.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_4316257
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         'C26 H30 O2'
_chemical_formula_sum            'C26 H30 O2'
_chemical_formula_weight         374.50
_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                 101.009(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6805(15)
_cell_length_b                   18.731(3)
_cell_length_c                   11.942(2)
_cell_measurement_reflns_used    145
_cell_measurement_temperature    164(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     2125.5(6)
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      164(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  SIEMENS_SMART_CCD
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_sigmaI/netI    0.0807
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            30201
_diffrn_reflns_theta_full        27.30
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1600
_diffrn_standards_number         266
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0029(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.0700
_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)+(0.05P)²+0.9P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1472
_reflns_number_gt                2773
_reflns_number_total             4908
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ic100754k_si_002_09.cif
_cod_data_source_block           M7
_cod_original_cell_volume        2125.6(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4316257
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
O2 O 0.42375(18) 0.19174(9) 0.55501(13) 0.0461(5) Uani 1 1 d . . .
O1 O 0.00279(17) 0.09517(9) 0.20887(14) 0.0424(4) Uani 1 1 d . . .
C16 C 0.5596(2) 0.16870(12) 0.14700(18) 0.0300(5) Uani 1 1 d . . .
H16A H 0.5407 0.2180 0.1332 0.036 Uiso 1 1 calc R . .
C11 C 0.5411(2) 0.13957(11) 0.25025(18) 0.0269(5) Uani 1 1 d . . .
C15 C 0.6050(2) 0.12791(12) 0.06289(19) 0.0333(5) Uani 1 1 d . . .
C1 C 0.4914(2) 0.18497(11) 0.34246(17) 0.0275(5) Uani 1 1 d . . .
H1A H 0.5576 0.1738 0.4154 0.033 Uiso 1 1 calc R . .
C3 C 0.2422(2) 0.13974(11) 0.27285(19) 0.0316(5) Uani 1 1 d . . .
H3A H 0.2604 0.1385 0.1975 0.038 Uiso 1 1 calc R . .
C2 C 0.3465(2) 0.16310(11) 0.36135(18) 0.0283(5) Uani 1 1 d . . .
C12 C 0.5694(2) 0.06665(12) 0.27164(19) 0.0319(5) Uani 1 1 d . . .
C7 C 0.3165(2) 0.16573(11) 0.47131(19) 0.0338(5) Uani 1 1 d . . .
C19 C 0.5040(2) 0.26533(11) 0.32493(17) 0.0289(5) Uani 1 1 d . . .
C17 C 0.5574(3) 0.03202(12) 0.3828(2) 0.0416(6) Uani 1 1 d . . .
H17A H 0.5888 -0.0177 0.3827 0.062 Uiso 1 1 calc R . .
H17B H 0.4592 0.0334 0.3925 0.062 Uiso 1 1 calc R . .
H17C H 0.6165 0.0578 0.4458 0.062 Uiso 1 1 calc R . .
C13 C 0.6121(3) 0.02653(12) 0.1866(2) 0.0400(6) Uani 1 1 d . . .
H13A H 0.6298 -0.0230 0.1992 0.048 Uiso 1 1 calc R . .
C5 C 0.0839(2) 0.11767(11) 0.4035(2) 0.0356(6) Uani 1 1 d . . .
C23 C 0.3984(3) 0.37854(12) 0.2518(2) 0.0398(6) Uani 1 1 d . . .
C18 C 0.6292(3) 0.16135(14) -0.0473(2) 0.0480(7) Uani 1 1 d . . .
H18A H 0.7305 0.1638 -0.0467 0.072 Uiso 1 1 calc R . .
H18B H 0.5893 0.2096 -0.0545 0.072 Uiso 1 1 calc R . .
H18C H 0.5835 0.1322 -0.1121 0.072 Uiso 1 1 calc R . .
C20 C 0.6321(2) 0.29996(12) 0.36575(19) 0.0358(6) Uani 1 1 d . . .
C14 C 0.6296(2) 0.05607(13) 0.0843(2) 0.0401(6) Uani 1 1 d . . .
H14A H 0.6589 0.0268 0.0282 0.048 Uiso 1 1 calc R . .
C6 C 0.1873(3) 0.14210(12) 0.4912(2) 0.0375(6) Uani 1 1 d . . .
H6A H 0.1697 0.1427 0.5667 0.045 Uiso 1 1 calc R . .
C4 C 0.1114(2) 0.11813(11) 0.2924(2) 0.0333(5) Uani 1 1 d . . .
C24 C 0.3901(2) 0.30511(12) 0.26924(18) 0.0330(5) Uani 1 1 d . . .
H24A H 0.3034 0.2814 0.2421 0.040 Uiso 1 1 calc R . .
C21 C 0.6398(3) 0.37306(13) 0.3470(2) 0.0448(7) Uani 1 1 d . . .
H21A H 0.7262 0.3971 0.3739 0.054 Uiso 1 1 calc R . .
C22 C 0.5269(3) 0.41171(13) 0.2908(2) 0.0455(7) Uani 1 1 d . . .
H22A H 0.5368 0.4614 0.2785 0.055 Uiso 1 1 calc R . .
C26 C 0.2715(3) 0.42058(14) 0.1951(2) 0.0565(8) Uani 1 1 d . . .
H26A H 0.2041 0.3885 0.1482 0.085 Uiso 1 1 calc R . .
H26B H 0.3008 0.4576 0.1466 0.085 Uiso 1 1 calc R . .
H26C H 0.2272 0.4429 0.2535 0.085 Uiso 1 1 calc R . .
C9 C -0.0547(3) 0.08952(14) 0.4248(2) 0.0509(7) Uani 1 1 d . . .
H9A H -0.0564 0.0374 0.4175 0.076 Uiso 1 1 calc R . .
H9B H -0.1318 0.1100 0.3688 0.076 Uiso 1 1 calc R . .
H9C H -0.0662 0.1028 0.5018 0.076 Uiso 1 1 calc R . .
C8 C 0.0227(3) 0.09697(15) 0.0942(2) 0.0503(7) Uani 1 1 d . . .
H8A H 0.0427 0.1460 0.0737 0.075 Uiso 1 1 calc R . .
H8B H -0.0629 0.0801 0.0436 0.075 Uiso 1 1 calc R . .
H8C H 0.1019 0.0661 0.0861 0.075 Uiso 1 1 calc R . .
C10 C 0.3930(3) 0.20557(15) 0.6643(2) 0.0537(7) Uani 1 1 d . . .
H10A H 0.3118 0.2377 0.6568 0.080 Uiso 1 1 calc R . .
H10B H 0.4747 0.2280 0.7127 0.080 Uiso 1 1 calc R . .
H10C H 0.3713 0.1606 0.6992 0.080 Uiso 1 1 calc R . .
C25 C 0.7591(3) 0.26084(14) 0.4291(2) 0.0532(7) Uani 1 1 d . . .
H25A H 0.8363 0.2947 0.4526 0.080 Uiso 1 1 calc R . .
H25B H 0.7880 0.2245 0.3792 0.080 Uiso 1 1 calc R . .
H25C H 0.7356 0.2378 0.4968 0.080 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'
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
C7 O2 C10 117.95(19) . . ?
C4 O1 C8 117.87(18) . . ?
C11 C16 C15 122.3(2) . . ?
C16 C11 C12 119.21(19) . . ?
C16 C11 C1 121.89(19) . . ?
C12 C11 C1 118.90(18) . . ?
C14 C15 C16 117.8(2) . . ?
C14 C15 C18 120.9(2) . . ?
C16 C15 C18 121.3(2) . . ?
C2 C1 C19 112.73(17) . . ?
C2 C1 C11 112.38(17) . . ?
C19 C1 C11 113.71(17) . . ?
C2 C3 C4 121.2(2) . . ?
C3 C2 C7 118.4(2) . . ?
C3 C2 C1 122.07(18) . . ?
C7 C2 C1 119.54(19) . . ?
C13 C12 C11 117.9(2) . . ?
C13 C12 C17 119.8(2) . . ?
C11 C12 C17 122.30(19) . . ?
O2 C7 C6 124.4(2) . . ?
O2 C7 C2 115.36(19) . . ?
C6 C7 C2 120.3(2) . . ?
C24 C19 C20 119.1(2) . . ?
C24 C19 C1 121.1(2) . . ?
C20 C19 C1 119.8(2) . . ?
C14 C13 C12 122.3(2) . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 C9 121.8(2) . . ?
C4 C5 C9 119.9(2) . . ?
C22 C23 C24 117.7(2) . . ?
C22 C23 C26 121.2(2) . . ?
C24 C23 C26 121.1(2) . . ?
C21 C20 C19 118.1(2) . . ?
C21 C20 C25 119.7(2) . . ?
C19 C20 C25 122.2(2) . . ?
C13 C14 C15 120.5(2) . . ?
C5 C6 C7 121.5(2) . . ?
O1 C4 C3 124.4(2) . . ?
O1 C4 C5 115.3(2) . . ?
C3 C4 C5 120.3(2) . . ?
C19 C24 C23 122.4(2) . . ?
C22 C21 C20 122.3(2) . . ?
C21 C22 C23 120.4(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
O2 C7 1.385(3) . ?
O2 C10 1.417(3) . ?
O1 C4 1.373(3) . ?
O1 C8 1.419(3) . ?
C16 C11 1.391(3) . ?
C16 C15 1.398(3) . ?
C11 C12 1.407(3) . ?
C11 C1 1.539(3) . ?
C15 C14 1.382(3) . ?
C15 C18 1.516(3) . ?
C1 C2 1.519(3) . ?
C1 C19 1.528(3) . ?
C3 C2 1.386(3) . ?
C3 C4 1.391(3) . ?
C2 C7 1.399(3) . ?
C12 C13 1.388(3) . ?
C12 C17 1.502(3) . ?
C7 C6 1.389(3) . ?
C19 C24 1.391(3) . ?
C19 C20 1.401(3) . ?
C13 C14 1.381(3) . ?
C5 C6 1.382(3) . ?
C5 C4 1.402(3) . ?
C5 C9 1.508(3) . ?
C23 C22 1.389(4) . ?
C23 C24 1.396(3) . ?
C23 C26 1.507(4) . ?
C20 C21 1.392(3) . ?
C20 C25 1.505(3) . ?
C21 C22 1.374(4) . ?
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
C15 C16 C11 C12 0.3(3) . . . . ?
C15 C16 C11 C1 179.8(2) . . . . ?
C11 C16 C15 C14 1.0(3) . . . . ?
C11 C16 C15 C18 -177.9(2) . . . . ?
C16 C11 C1 C2 113.7(2) . . . . ?
C12 C11 C1 C2 -66.8(2) . . . . ?
C16 C11 C1 C19 -15.9(3) . . . . ?
C12 C11 C1 C19 163.6(2) . . . . ?
C4 C3 C2 C7 -1.1(3) . . . . ?
C4 C3 C2 C1 178.26(19) . . . . ?
C19 C1 C2 C3 94.9(2) . . . . ?
C11 C1 C2 C3 -35.2(3) . . . . ?
C19 C1 C2 C7 -85.7(2) . . . . ?
C11 C1 C2 C7 144.21(19) . . . . ?
C16 C11 C12 C13 -1.4(3) . . . . ?
C1 C11 C12 C13 179.0(2) . . . . ?
C16 C11 C12 C17 177.5(2) . . . . ?
C1 C11 C12 C17 -2.0(3) . . . . ?
C10 O2 C7 C6 -10.2(3) . . . . ?
C10 O2 C7 C2 170.9(2) . . . . ?
C3 C2 C7 O2 -178.00(19) . . . . ?
C1 C2 C7 O2 2.6(3) . . . . ?
C3 C2 C7 C6 3.1(3) . . . . ?
C1 C2 C7 C6 -176.3(2) . . . . ?
C2 C1 C19 C24 -34.0(3) . . . . ?
C11 C1 C19 C24 95.4(2) . . . . ?
C2 C1 C19 C20 145.76(19) . . . . ?
C11 C1 C19 C20 -84.8(2) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C17 C12 C13 C14 -177.7(2) . . . . ?
C24 C19 C20 C21 -0.9(3) . . . . ?
C1 C19 C20 C21 179.28(19) . . . . ?
C24 C19 C20 C25 178.6(2) . . . . ?
C1 C19 C20 C25 -1.2(3) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C16 C15 C14 C13 -1.2(3) . . . . ?
C18 C15 C14 C13 177.7(2) . . . . ?
C4 C5 C6 C7 -0.9(3) . . . . ?
C9 C5 C6 C7 177.8(2) . . . . ?
O2 C7 C6 C5 179.1(2) . . . . ?
C2 C7 C6 C5 -2.1(3) . . . . ?
C8 O1 C4 C3 -3.3(3) . . . . ?
C8 O1 C4 C5 177.7(2) . . . . ?
C2 C3 C4 O1 179.2(2) . . . . ?
C2 C3 C4 C5 -1.9(3) . . . . ?
C6 C5 C4 O1 -178.16(19) . . . . ?
C9 C5 C4 O1 3.1(3) . . . . ?
C6 C5 C4 C3 2.8(3) . . . . ?
C9 C5 C4 C3 -175.9(2) . . . . ?
C20 C19 C24 C23 0.3(3) . . . . ?
C1 C19 C24 C23 -179.91(19) . . . . ?
C22 C23 C24 C19 1.0(3) . . . . ?
C26 C23 C24 C19 -177.7(2) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C25 C20 C21 C22 -179.3(2) . . . . ?
C20 C21 C22 C23 1.0(4) . . . . ?
C24 C23 C22 C21 -1.6(3) . . . . ?
C26 C23 C22 C21 177.0(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661009
