#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:16:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178556 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/64/4066431.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_4066431
loop_
_publ_author_name
'Enk, Barbara'
'Eisenstecken, Daniela'
'Kopacka, Holger'
'Wurst, Klaus'
'Müller, Thomas'
'Pevny, Florian'
'Winter, Rainer F.'
'Bildstein, Benno'
_publ_section_title
;
 Doubly N-Functionalized Pentafulvenes and Redox-Responsive [N,N]- and
 [N,C,N]-Pincer Bis(imidoyl)pentamethylruthenocene Metalloligands
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              3169
_journal_paper_doi               10.1021/om100458h
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C43 H48 N2'
_chemical_formula_weight         592.83
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 104.018(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8897(3)
_cell_length_b                   11.0132(2)
_cell_length_c                   24.4061(6)
_cell_measurement_reflns_used    14049
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.0
_cell_volume                     3622.22(14)
_computing_data_collection       COLLECT
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9875
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.39
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.026
_refine_ls_extinction_coef       0.0147(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3153
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0459
_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)+(0.0607P)²+1.4578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1272
_reflns_number_gt                2633
_reflns_number_total             3153
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100458h_si_002.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4066431
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
N1 N 0.54131(8) 0.22411(10) 0.30478(5) 0.0422(3) Uani 1 1 d D
H1N H 0.515(2) 0.212(2) 0.2679(8) 0.039(8) Uiso 0.50 1 d PD
C1 C 0.56245(9) 0.33811(12) 0.31821(6) 0.0431(3) Uani 1 1 d .
C2 C 0.53133(9) 0.43446(12) 0.27897(6) 0.0433(3) Uani 1 1 d .
C3 C 0.54952(11) 0.55746(13) 0.29368(7) 0.0573(4) Uani 1 1 d .
H3 H 0.5894 0.5855 0.3281 0.069 Uiso 1 1 calc .
C4 C 0.5000 0.63062(18) 0.2500 0.0667(7) Uani 1 2 d S
H4 H 0.5000 0.7160 0.2500 0.080 Uiso 1 2 calc S
C5 C 0.62283(12) 0.36815(14) 0.37622(6) 0.0584(4) Uani 1 1 d .
C6 C 0.71826(14) 0.32402(16) 0.39349(8) 0.0739(6) Uani 1 1 d .
H6 H 0.7444 0.2754 0.3689 0.089 Uiso 1 1 calc .
C7 C 0.7761(2) 0.3509(3) 0.44701(12) 0.1153(11) Uani 1 1 d .
H7 H 0.8407 0.3194 0.4587 0.138 Uiso 1 1 calc .
C8 C 0.7392(4) 0.4231(4) 0.48255(11) 0.1494(18) Uani 1 1 d .
H8 H 0.7790 0.4431 0.5183 0.179 Uiso 1 1 calc .
C9 C 0.6455(3) 0.4656(3) 0.46629(12) 0.1385(14) Uani 1 1 d .
H9 H 0.6199 0.5133 0.4914 0.166 Uiso 1 1 calc .
C10 C 0.58638(18) 0.4401(2) 0.41312(9) 0.0957(7) Uani 1 1 d .
H10 H 0.5216 0.4715 0.4021 0.115 Uiso 1 1 calc .
C11 C 0.55493(9) 0.12308(12) 0.34289(5) 0.0415(3) Uani 1 1 d .
C12 C 0.62012(11) 0.03045(13) 0.33639(6) 0.0515(4) Uani 1 1 d .
C13 C 0.62362(13) -0.07396(15) 0.36894(7) 0.0649(5) Uani 1 1 d .
H13 H 0.6672 -0.1369 0.3651 0.078 Uiso 1 1 calc .
C14 C 0.56546(14) -0.08746(16) 0.40626(7) 0.0686(5) Uani 1 1 d .
H14 H 0.5688 -0.1590 0.4276 0.082 Uiso 1 1 calc .
C15 C 0.50220(13) 0.00390(15) 0.41238(7) 0.0609(4) Uani 1 1 d .
H15 H 0.4631 -0.0055 0.4386 0.073 Uiso 1 1 calc .
C16 C 0.49413(10) 0.11025(13) 0.38090(6) 0.0473(4) Uani 1 1 d .
C17 C 0.68588(13) 0.03799(15) 0.29523(8) 0.0655(5) Uani 1 1 d .
H17 H 0.6749 0.1178 0.2761 0.079 Uiso 1 1 calc .
C18 C 0.41549(12) 0.20176(14) 0.38625(6) 0.0551(4) Uani 1 1 d .
H18 H 0.4273 0.2772 0.3668 0.066 Uiso 1 1 calc .
C171 C 0.65976(18) -0.06137(18) 0.25012(9) 0.0834(6) Uani 1 1 d .
H17A H 0.7028 -0.0543 0.2243 0.125 Uiso 1 1 calc .
H17B H 0.5912 -0.0522 0.2293 0.125 Uiso 1 1 calc .
H17C H 0.6688 -0.1405 0.2681 0.125 Uiso 1 1 calc .
C172 C 0.79573(15) 0.0288(2) 0.32613(12) 0.1004(8) Uani 1 1 d .
H17D H 0.8362 0.0321 0.2989 0.151 Uiso 1 1 calc .
H17E H 0.8074 -0.0474 0.3466 0.151 Uiso 1 1 calc .
H17F H 0.8131 0.0958 0.3525 0.151 Uiso 1 1 calc .
C181 C 0.31246(13) 0.15441(16) 0.35727(9) 0.0731(5) Uani 1 1 d .
H18A H 0.2629 0.2139 0.3609 0.110 Uiso 1 1 calc .
H18B H 0.3002 0.0789 0.3749 0.110 Uiso 1 1 calc .
H18C H 0.3089 0.1403 0.3176 0.110 Uiso 1 1 calc .
C182 C 0.41922(18) 0.2332(2) 0.44751(9) 0.0916(7) Uani 1 1 d .
H18D H 0.3680 0.2923 0.4488 0.137 Uiso 1 1 calc .
H18E H 0.4837 0.2669 0.4653 0.137 Uiso 1 1 calc .
H18F H 0.4083 0.1603 0.4675 0.137 Uiso 1 1 calc .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C11 126.45(11) . .
N1 C1 C2 122.11(12) . .
N1 C1 C5 119.18(12) . .
C2 C1 C5 118.70(12) . .
C3 C2 C1 122.59(13) . .
C3 C2 C2 105.84(9) . 2_655
C1 C2 C2 131.24(7) . 2_655
C4 C3 C2 109.86(14) . .
C3 C4 C3 108.53(18) 2_655 .
C6 C5 C10 118.62(17) . .
C6 C5 C1 119.21(15) . .
C10 C5 C1 122.17(17) . .
C5 C6 C7 120.4(2) . .
C8 C7 C6 120.1(3) . .
C9 C8 C7 119.9(2) . .
C8 C9 C10 121.0(3) . .
C5 C10 C9 119.9(3) . .
C12 C11 C16 120.73(12) . .
C12 C11 N1 118.68(12) . .
C16 C11 N1 120.05(11) . .
C13 C12 C11 118.16(13) . .
C13 C12 C17 118.71(13) . .
C11 C12 C17 123.12(13) . .
C14 C13 C12 121.79(14) . .
C13 C14 C15 119.52(14) . .
C14 C15 C16 121.83(14) . .
C15 C16 C11 117.96(13) . .
C15 C16 C18 118.43(13) . .
C11 C16 C18 123.46(12) . .
C12 C17 C171 111.19(14) . .
C12 C17 C172 111.01(16) . .
C171 C17 C172 109.92(15) . .
C16 C18 C182 112.44(14) . .
C16 C18 C181 110.33(12) . .
C182 C18 C181 109.73(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3127(17) .
N1 C11 1.4331(16) .
C1 C2 1.4246(19) .
C1 C5 1.497(2) .
C2 C3 1.4084(19) .
C2 C2 1.470(3) 2_655
C3 C4 1.380(2) .
C4 C3 1.380(2) 2_655
C5 C6 1.378(3) .
C5 C10 1.384(3) .
C6 C7 1.389(3) .
C7 C8 1.364(5) .
C8 C9 1.349(5) .
C9 C10 1.386(4) .
C11 C12 1.3983(19) .
C11 C16 1.4046(19) .
C12 C13 1.392(2) .
C12 C17 1.515(2) .
C13 C14 1.364(2) .
C14 C15 1.368(2) .
C15 C16 1.390(2) .
C16 C18 1.515(2) .
C17 C171 1.532(3) .
C17 C172 1.533(3) .
C18 C182 1.523(2) .
C18 C181 1.526(2) .
