#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:20:46 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179242 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/62/4316262.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_4316262
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 O'
_chemical_formula_sum            'C17 H20 O'
_chemical_formula_weight         240.33
_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                96.266(18)
_cell_angle_beta                 111.921(16)
_cell_angle_gamma                104.374(15)
_cell_formula_units_Z            4
_cell_length_a                   10.144(2)
_cell_length_b                   11.712(2)
_cell_length_c                   13.472(3)
_cell_measurement_reflns_used    98
_cell_measurement_temperature    166(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     1401.6(5)
_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      166(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.950
_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  0.1082
_diffrn_reflns_av_sigmaI/netI    0.1751
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18945
_diffrn_reflns_theta_full        26.70
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1200
_diffrn_standards_number         107
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0130(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         6166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.2225
_refine_ls_R_factor_gt           0.0714
_refine_ls_shift/su_max          0.003
_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] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1533
_reflns_number_gt                2382
_reflns_number_total             6166
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ic100754k_si_002_14.cif
_cod_data_source_block           S4
_cod_original_cell_volume        1401.7(5)
_cod_database_code               4316262
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 0.4982(2) 0.47983(15) 0.36260(15) 0.0322(5) Uani 1 1 d . . .
H1B H 0.5723 0.5224 0.4198 0.048 Uiso 1 1 calc R . .
O2 O 0.2732(2) 0.39125(15) 0.43156(16) 0.0355(5) Uani 1 1 d . . .
H2A H 0.3295 0.3947 0.3987 0.053 Uiso 1 1 calc R . .
C7 C 0.3890(3) 0.6723(2) 0.3984(2) 0.0298(7) Uani 1 1 d . . .
H7A H 0.3935 0.6132 0.4414 0.036 Uiso 1 1 calc R . .
C2 C 0.4262(3) 0.6579(2) 0.3086(2) 0.0273(7) Uani 1 1 d . . .
C19 C 0.1662(3) 0.2720(2) 0.5324(2) 0.0279(7) Uani 1 1 d . . .
C18 C 0.2170(3) 0.2680(2) 0.4389(2) 0.0288(7) Uani 1 1 d . . .
H18A H 0.3017 0.2335 0.4593 0.035 Uiso 1 1 calc R . .
C27 C 0.0962(3) 0.1919(2) 0.3288(2) 0.0317(7) Uani 1 1 d . . .
C10 C 0.3532(3) 0.4582(2) 0.1743(2) 0.0286(7) Uani 1 1 d . . .
C15 C 0.2030(3) 0.4394(2) 0.1472(2) 0.0343(8) Uani 1 1 d . . .
H15A H 0.1752 0.4882 0.1920 0.041 Uiso 1 1 calc R . .
C3 C 0.4209(3) 0.7448(2) 0.2449(2) 0.0306(7) Uani 1 1 d . . .
C32 C -0.0533(3) 0.1765(2) 0.3034(2) 0.0370(8) Uani 1 1 d . . .
H32A H -0.0790 0.2153 0.3560 0.044 Uiso 1 1 calc R . .
C24 C 0.1288(3) 0.3706(3) 0.5662(2) 0.0332(8) Uani 1 1 d . . .
H24A H 0.1345 0.4355 0.5297 0.040 Uiso 1 1 calc R . .
C4 C 0.3752(3) 0.8419(3) 0.2723(3) 0.0405(8) Uani 1 1 d . . .
H4A H 0.3687 0.9005 0.2287 0.049 Uiso 1 1 calc R . .
C20 C 0.1593(3) 0.1755(3) 0.5848(2) 0.0333(8) Uani 1 1 d . . .
C1 C 0.4705(3) 0.5487(2) 0.2787(2) 0.0273(7) Uani 1 1 d . . .
H1A H 0.5646 0.5782 0.2681 0.033 Uiso 1 1 calc R . .
C6 C 0.3457(3) 0.7704(3) 0.4265(2) 0.0354(8) Uani 1 1 d . . .
C22 C 0.0760(3) 0.2815(3) 0.7026(2) 0.0474(9) Uani 1 1 d . . .
H22A H 0.0451 0.2834 0.7610 0.057 Uiso 1 1 calc R . .
C25 C 0.2019(3) 0.0669(2) 0.5526(2) 0.0450(9) Uani 1 1 d . . .
H25A H 0.1462 0.0335 0.4734 0.067 Uiso 1 1 calc R . .
H25B H 0.1777 0.0053 0.5923 0.067 Uiso 1 1 calc R . .
H25C H 0.3095 0.0916 0.5713 0.067 Uiso 1 1 calc R . .
C23 C 0.0828(3) 0.3785(3) 0.6517(2) 0.0384(8) Uani 1 1 d . . .
C21 C 0.1129(3) 0.1827(3) 0.6701(2) 0.0439(9) Uani 1 1 d . . .
H21A H 0.1067 0.1179 0.7066 0.053 Uiso 1 1 calc R . .
C5 C 0.3390(3) 0.8551(3) 0.3618(3) 0.0426(9) Uani 1 1 d . . .
H5A H 0.3092 0.9228 0.3788 0.051 Uiso 1 1 calc R . .
C11 C 0.3982(4) 0.3877(3) 0.1094(2) 0.0375(8) Uani 1 1 d . . .
C12 C 0.2860(4) 0.2999(3) 0.0191(3) 0.0483(9) Uani 1 1 d . . .
H12A H 0.3130 0.2510 -0.0263 0.058 Uiso 1 1 calc R . .
C28 C 0.1386(4) 0.1367(2) 0.2518(3) 0.0385(8) Uani 1 1 d . . .
C8 C 0.4643(3) 0.7355(3) 0.1491(2) 0.0409(8) Uani 1 1 d . . .
H8A H 0.5698 0.7395 0.1757 0.061 Uiso 1 1 calc R . .
H8B H 0.4495 0.8026 0.1132 0.061 Uiso 1 1 calc R . .
H8C H 0.4019 0.6585 0.0963 0.061 Uiso 1 1 calc R . .
C29 C 0.0221(5) 0.0650(3) 0.1528(3) 0.0545(10) Uani 1 1 d . . .
H29A H 0.0466 0.0254 0.0999 0.065 Uiso 1 1 calc R . .
C31 C -0.1688(4) 0.1060(3) 0.2032(3) 0.0459(9) Uani 1 1 d . . .
C9 C 0.3067(3) 0.7839(3) 0.5245(2) 0.0501(9) Uani 1 1 d . . .
H9A H 0.3685 0.8629 0.5743 0.075 Uiso 1 1 calc R . .
H9B H 0.3257 0.7196 0.5634 0.075 Uiso 1 1 calc R . .
H9C H 0.2008 0.7780 0.4993 0.075 Uiso 1 1 calc R . .
C13 C 0.1360(4) 0.2824(3) -0.0058(3) 0.0472(9) Uani 1 1 d . . .
H13A H 0.0626 0.2212 -0.0676 0.057 Uiso 1 1 calc R . .
C14 C 0.0901(4) 0.3518(3) 0.0569(3) 0.0408(8) Uani 1 1 d . . .
C30 C -0.1259(5) 0.0499(3) 0.1291(3) 0.0551(10) Uani 1 1 d . . .
H30A H -0.2006 0.0001 0.0609 0.066 Uiso 1 1 calc R . .
C17 C -0.0727(3) 0.3340(3) 0.0293(3) 0.0565(10) Uani 1 1 d . . .
H17A H -0.0935 0.4105 0.0199 0.085 Uiso 1 1 calc R . .
H17B H -0.0964 0.3077 0.0889 0.085 Uiso 1 1 calc R . .
H17C H -0.1343 0.2723 -0.0390 0.085 Uiso 1 1 calc R . .
C26 C 0.0408(4) 0.4856(3) 0.6865(3) 0.0588(10) Uani 1 1 d . . .
H26A H -0.0682 0.4667 0.6519 0.088 Uiso 1 1 calc R . .
H26B H 0.0874 0.5556 0.6637 0.088 Uiso 1 1 calc R . .
H26C H 0.0758 0.5043 0.7665 0.088 Uiso 1 1 calc R . .
C33 C 0.2989(4) 0.1534(3) 0.2718(3) 0.0529(10) Uani 1 1 d . . .
H33A H 0.3025 0.1036 0.2101 0.079 Uiso 1 1 calc R . .
H33B H 0.3491 0.1288 0.3397 0.079 Uiso 1 1 calc R . .
H33C H 0.3498 0.2387 0.2787 0.079 Uiso 1 1 calc R . .
C34 C -0.3291(4) 0.0934(3) 0.1785(3) 0.0672(11) Uani 1 1 d . . .
H34A H -0.3692 0.0278 0.2089 0.101 Uiso 1 1 calc R . .
H34B H -0.3873 0.0748 0.0988 0.101 Uiso 1 1 calc R . .
H34C H -0.3358 0.1693 0.2116 0.101 Uiso 1 1 calc R . .
C16 C 0.5605(4) 0.4029(3) 0.1361(3) 0.0574(10) Uani 1 1 d . . .
H16A H 0.5678 0.3386 0.0874 0.086 Uiso 1 1 calc R . .
H16B H 0.6114 0.3982 0.2126 0.086 Uiso 1 1 calc R . .
H16C H 0.6078 0.4818 0.1258 0.086 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
C6 C7 C2 122.2(3) . . ?
C3 C2 C7 119.4(3) . . ?
C3 C2 C1 119.6(2) . . ?
C7 C2 C1 121.0(2) . . ?
C24 C19 C20 119.9(3) . . ?
C24 C19 C18 120.6(2) . . ?
C20 C19 C18 119.4(3) . . ?
O2 C18 C27 110.8(2) . . ?
O2 C18 C19 107.4(2) . . ?
C27 C18 C19 114.3(2) . . ?
C32 C27 C28 120.1(3) . . ?
C32 C27 C18 120.8(3) . . ?
C28 C27 C18 119.1(3) . . ?
C15 C10 C11 120.0(3) . . ?
C15 C10 C1 120.2(3) . . ?
C11 C10 C1 119.7(3) . . ?
C10 C15 C14 122.9(3) . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 C8 120.2(3) . . ?
C2 C3 C8 121.6(3) . . ?
C27 C32 C31 122.8(3) . . ?
C19 C24 C23 122.6(3) . . ?
C5 C4 C3 121.7(3) . . ?
C19 C20 C21 117.7(3) . . ?
C19 C20 C25 122.0(3) . . ?
C21 C20 C25 120.2(3) . . ?
O1 C1 C2 113.0(2) . . ?
O1 C1 C10 105.2(2) . . ?
C2 C1 C10 114.0(2) . . ?
C5 C6 C7 117.8(3) . . ?
C5 C6 C9 121.2(3) . . ?
C7 C6 C9 121.0(3) . . ?
C21 C22 C23 121.5(3) . . ?
C22 C23 C24 116.7(3) . . ?
C22 C23 C26 121.4(3) . . ?
C24 C23 C26 121.9(3) . . ?
C22 C21 C20 121.6(3) . . ?
C6 C5 C4 120.7(3) . . ?
C12 C11 C10 117.4(3) . . ?
C12 C11 C16 120.3(3) . . ?
C10 C11 C16 122.2(3) . . ?
C13 C12 C11 121.4(3) . . ?
C29 C28 C27 116.5(3) . . ?
C29 C28 C33 120.4(3) . . ?
C27 C28 C33 123.1(3) . . ?
C30 C29 C28 122.7(3) . . ?
C30 C31 C32 116.5(3) . . ?
C30 C31 C34 122.4(3) . . ?
C32 C31 C34 121.0(3) . . ?
C12 C13 C14 121.8(3) . . ?
C13 C14 C15 116.5(3) . . ?
C13 C14 C17 121.9(3) . . ?
C15 C14 C17 121.6(3) . . ?
C29 C30 C31 121.3(3) . . ?
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 C1 1.442(3) . ?
O2 C18 1.443(3) . ?
C7 C6 1.391(4) . ?
C7 C2 1.400(3) . ?
C2 C3 1.400(4) . ?
C2 C1 1.519(3) . ?
C19 C24 1.385(4) . ?
C19 C20 1.396(4) . ?
C19 C18 1.529(4) . ?
C18 C27 1.519(4) . ?
C27 C32 1.383(4) . ?
C27 C28 1.415(4) . ?
C10 C15 1.380(4) . ?
C10 C11 1.409(4) . ?
C10 C1 1.522(4) . ?
C15 C14 1.396(4) . ?
C3 C4 1.394(4) . ?
C3 C8 1.513(4) . ?
C32 C31 1.404(4) . ?
C24 C23 1.397(4) . ?
C4 C5 1.389(4) . ?
C20 C21 1.397(4) . ?
C20 C25 1.512(4) . ?
C6 C5 1.389(4) . ?
C6 C9 1.517(4) . ?
C22 C21 1.378(4) . ?
C22 C23 1.389(4) . ?
C23 C26 1.504(4) . ?
C11 C12 1.394(4) . ?
C11 C16 1.506(4) . ?
C12 C13 1.385(4) . ?
C28 C29 1.403(4) . ?
C28 C33 1.504(4) . ?
C29 C30 1.373(4) . ?
C31 C30 1.393(4) . ?
C31 C34 1.498(4) . ?
C13 C14 1.387(4) . ?
C14 C17 1.504(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
C6 C7 C2 C3 0.3(4) . . . . ?
C6 C7 C2 C1 -178.9(3) . . . . ?
C24 C19 C18 O2 22.9(3) . . . . ?
C20 C19 C18 O2 -156.4(2) . . . . ?
C24 C19 C18 C27 -100.5(3) . . . . ?
C20 C19 C18 C27 80.2(3) . . . . ?
O2 C18 C27 C32 -93.2(3) . . . . ?
C19 C18 C27 C32 28.3(4) . . . . ?
O2 C18 C27 C28 86.7(3) . . . . ?
C19 C18 C27 C28 -151.8(3) . . . . ?
C11 C10 C15 C14 0.3(4) . . . . ?
C1 C10 C15 C14 -175.4(3) . . . . ?
C7 C2 C3 C4 -1.3(4) . . . . ?
C1 C2 C3 C4 178.0(2) . . . . ?
C7 C2 C3 C8 178.2(3) . . . . ?
C1 C2 C3 C8 -2.5(4) . . . . ?
C28 C27 C32 C31 0.8(4) . . . . ?
C18 C27 C32 C31 -179.3(3) . . . . ?
C20 C19 C24 C23 -0.2(4) . . . . ?
C18 C19 C24 C23 -179.5(3) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C8 C3 C4 C5 -178.0(3) . . . . ?
C24 C19 C20 C21 0.5(4) . . . . ?
C18 C19 C20 C21 179.8(3) . . . . ?
C24 C19 C20 C25 -178.7(3) . . . . ?
C18 C19 C20 C25 0.6(4) . . . . ?
C3 C2 C1 O1 169.0(2) . . . . ?
C7 C2 C1 O1 -11.7(3) . . . . ?
C3 C2 C1 C10 -70.8(3) . . . . ?
C7 C2 C1 C10 108.4(3) . . . . ?
C15 C10 C1 O1 90.5(3) . . . . ?
C11 C10 C1 O1 -85.2(3) . . . . ?
C15 C10 C1 C2 -33.9(3) . . . . ?
C11 C10 C1 C2 150.4(2) . . . . ?
C2 C7 C6 C5 0.5(4) . . . . ?
C2 C7 C6 C9 -179.7(3) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C21 C22 C23 C26 179.3(3) . . . . ?
C19 C24 C23 C22 0.0(4) . . . . ?
C19 C24 C23 C26 -179.2(3) . . . . ?
C23 C22 C21 C20 0.2(5) . . . . ?
C19 C20 C21 C22 -0.4(4) . . . . ?
C25 C20 C21 C22 178.8(3) . . . . ?
C7 C6 C5 C4 -0.3(4) . . . . ?
C9 C6 C5 C4 179.9(3) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C15 C10 C11 C12 -0.4(4) . . . . ?
C1 C10 C11 C12 175.3(3) . . . . ?
C15 C10 C11 C16 -179.0(3) . . . . ?
C1 C10 C11 C16 -3.3(4) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C16 C11 C12 C13 178.6(3) . . . . ?
C32 C27 C28 C29 -1.7(4) . . . . ?
C18 C27 C28 C29 178.4(2) . . . . ?
C32 C27 C28 C33 177.5(3) . . . . ?
C18 C27 C28 C33 -2.4(4) . . . . ?
C27 C28 C29 C30 1.2(4) . . . . ?
C33 C28 C29 C30 -178.0(3) . . . . ?
C27 C32 C31 C30 0.6(4) . . . . ?
C27 C32 C31 C34 -179.0(3) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C12 C13 C14 C17 179.3(3) . . . . ?
C10 C15 C14 C13 0.2(4) . . . . ?
C10 C15 C14 C17 -179.7(3) . . . . ?
C28 C29 C30 C31 0.2(5) . . . . ?
C32 C31 C30 C29 -1.1(5) . . . . ?
C34 C31 C30 C29 178.5(3) . . . . ?
