#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:06:34 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178549 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/56/4065640.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_4065640
loop_
_publ_author_name
'McAdam, C. John'
'Robinson, Brian H.'
'Simpson, Jim'
'Tagg, Tei'
_publ_section_title
;
 Ferrocenyl−Naphthalimide Donor−Acceptor Dyads with Aromatic
 Spacer Groups
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              2474
_journal_paper_doi               10.1021/om1000452
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C24 H19 Br Fe'
_chemical_formula_sum            'C24 H19 Br Fe'
_chemical_formula_weight         443.15
_chemical_name_systematic
; 
(E)-4-bromo-4'-(ethenylferrocenyl)biphenyl 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 95.268(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.0896(2)
_cell_length_b                   7.8142(2)
_cell_length_c                   18.7986(6)
_cell_measurement_reflns_used    6483
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      63.37
_cell_measurement_theta_min      4.35
_cell_volume                     890.76(5)
_computing_cell_refinement       'APEXII & SAINT V7.12A (Bruker  2004)'
_computing_data_collection       'APEXII V1.0-27 (Bruker 2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Nonius APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16393
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.094
_exptl_absorpt_correction_T_max  0.857
_exptl_absorpt_correction_T_min  0.599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Bruker, 2004)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack(1983) 432 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.011(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0321P)²+0.8851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0682
_reflns_number_gt                3426
_reflns_number_total             3517
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om1000452_si_001.cif
_cod_data_source_block           Structure2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4065640
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
Br1 Br 1.22177(6) 0.15458(4) -0.282149(18) 0.03885(11) Uani 1 1 d . . .
C1 C 1.0673(5) 0.1743(4) -0.19886(16) 0.0255(6) Uani 1 1 d . . .
C2 C 0.8678(6) 0.0931(5) -0.19642(17) 0.0341(7) Uani 1 1 d . . .
H2 H 0.8008 0.0352 -0.2372 0.041 Uiso 1 1 calc R . .
C3 C 0.7664(5) 0.0970(5) -0.13365(17) 0.0309(7) Uani 1 1 d . . .
H3 H 0.6296 0.0396 -0.1317 0.037 Uiso 1 1 calc R . .
C4 C 0.8589(4) 0.1827(3) -0.07291(15) 0.0206(6) Uani 1 1 d . . .
C5 C 1.0560(5) 0.2688(4) -0.07930(18) 0.0279(7) Uani 1 1 d . . .
H5 H 1.1210 0.3318 -0.0396 0.033 Uiso 1 1 calc R . .
C6 C 1.1610(5) 0.2658(4) -0.14184(18) 0.0283(7) Uani 1 1 d . . .
H6 H 1.2952 0.3260 -0.1450 0.034 Uiso 1 1 calc R . .
C7 C 0.7546(5) 0.1800(4) -0.00427(16) 0.0252(6) Uani 1 1 d . A .
C8 C 0.5512(5) 0.1002(4) 0.00157(19) 0.0314(7) Uani 1 1 d . . .
H8 H 0.4779 0.0449 -0.0389 0.038 Uiso 1 1 calc R . .
C9 C 0.4548(7) 0.1010(5) 0.0662(2) 0.0469(11) Uani 1 1 d . A .
H9 H 0.3164 0.0464 0.0688 0.056 Uiso 1 1 calc R . .
C10 C 0.5578(8) 0.1806(5) 0.1273(2) 0.0537(13) Uani 1 1 d . . .
C11 C 0.7611(8) 0.2558(6) 0.1212(2) 0.0474(11) Uani 1 1 d . A .
H11 H 0.8365 0.3085 0.1620 0.057 Uiso 1 1 calc R . .
C12 C 0.8573(6) 0.2563(5) 0.05750(18) 0.0347(8) Uani 1 1 d . . .
H12 H 0.9967 0.3097 0.0555 0.042 Uiso 1 1 calc R A .
C13 C 0.4844(10) 0.2098(7) 0.2006(3) 0.0241(17) Uani 0.641(13) 1 d P A 1
H13 H 0.5683 0.2840 0.2326 0.029 Uiso 0.641(13) 1 calc PR A 1
C14 C 0.3085(9) 0.1362(7) 0.2217(3) 0.0253(16) Uani 0.641(13) 1 d P A 1
H14 H 0.2317 0.0492 0.1942 0.030 Uiso 0.641(13) 1 calc PR A 1
C13A C 0.3720(14) 0.1471(13) 0.1787(5) 0.018(3) Uani 0.359(13) 1 d P A 2
H13A H 0.2377 0.0890 0.1650 0.022 Uiso 0.359(13) 1 calc PR A 2
C14A C 0.4271(13) 0.2112(10) 0.2448(5) 0.015(3) Uani 0.359(13) 1 d P A 2
H14A H 0.5668 0.2590 0.2602 0.018 Uiso 0.359(13) 1 calc PR A 2
C15 C 0.2340(7) 0.1965(6) 0.2918(2) 0.0517(12) Uani 1 1 d . . .
C16 C 0.3073(6) 0.3094(5) 0.3490(2) 0.0444(10) Uani 1 1 d . A .
H16 H 0.4463 0.3654 0.3548 0.053 Uiso 1 1 calc R . .
C17 C 0.1380(5) 0.3239(4) 0.39590(18) 0.0271(7) Uani 1 1 d . . .
H17 H 0.1423 0.3914 0.4380 0.033 Uiso 1 1 calc R A .
C18 C -0.0373(5) 0.2193(4) 0.36810(17) 0.0271(6) Uani 1 1 d . A .
H18 H -0.1732 0.2039 0.3884 0.032 Uiso 1 1 calc R . .
C19 C 0.0223(6) 0.1409(6) 0.30498(17) 0.0407(8) Uani 1 1 d . A .
H19 H -0.0665 0.0631 0.2761 0.049 Uiso 1 1 calc R . .
Fe1 Fe 0.24187(7) 0.07590(6) 0.38951(2) 0.02210(10) Uani 1 1 d . A .
C20 C 0.5085(5) -0.0835(4) 0.40453(17) 0.0271(7) Uani 1 1 d . . .
H20 H 0.6337 -0.0833 0.3779 0.032 Uiso 1 1 calc R A .
C21 C 0.4859(5) 0.0128(4) 0.46767(18) 0.0282(7) Uani 1 1 d . A .
H21 H 0.5921 0.0888 0.4904 0.034 Uiso 1 1 calc R . .
C22 C 0.2752(6) -0.0256(5) 0.49045(17) 0.0317(7) Uani 1 1 d . . .
H22 H 0.2158 0.0200 0.5314 0.038 Uiso 1 1 calc R A .
C23 C 0.1694(5) -0.1435(4) 0.44162(18) 0.0310(7) Uani 1 1 d . A .
H23 H 0.0264 -0.1905 0.4442 0.037 Uiso 1 1 calc R . .
C24 C 0.3132(5) -0.1799(4) 0.38800(18) 0.0280(7) Uani 1 1 d . A .
H24 H 0.2837 -0.2549 0.3485 0.034 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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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_publ_flag
C6 C1 C2 121.4(3) ?
C6 C1 Br1 119.0(2) ?
C2 C1 Br1 119.6(2) ?
C1 C2 C3 118.9(3) ?
C1 C2 H2 120.5 ?
C3 C2 H2 120.5 ?
C2 C3 C4 122.1(3) ?
C2 C3 H3 119.0 ?
C4 C3 H3 119.0 ?
C5 C4 C3 116.6(3) ?
C5 C4 C7 121.4(3) ?
C3 C4 C7 122.0(3) ?
C6 C5 C4 122.2(3) ?
C6 C5 H5 118.9 ?
C4 C5 H5 118.9 ?
C1 C6 C5 118.8(3) ?
C1 C6 H6 120.6 ?
C5 C6 H6 120.6 ?
C8 C7 C12 117.1(3) ?
C8 C7 C4 121.7(3) ?
C12 C7 C4 121.3(3) ?
C9 C8 C7 120.8(3) ?
C9 C8 H8 119.6 ?
C7 C8 H8 119.6 ?
C8 C9 C10 121.4(4) ?
C8 C9 H9 119.3 ?
C10 C9 H9 119.3 ?
C11 C10 C9 117.2(3) ?
C11 C10 C13 110.7(5) ?
C9 C10 C13 132.0(5) ?
C11 C10 C13A 144.9(5) ?
C9 C10 C13A 97.8(5) ?
C12 C11 C10 121.7(4) ?
C12 C11 H11 119.1 ?
C10 C11 H11 119.1 ?
C11 C12 C7 121.7(4) ?
C11 C12 H12 119.1 ?
C7 C12 H12 119.1 ?
C14 C13 C10 122.0(6) y
C14 C13 H13 119.0 ?
C10 C13 H13 119.0 ?
C13 C14 C15 116.5(6) y
C13 C14 H14 121.7 ?
C15 C14 H14 121.7 ?
C14A C13A C10 111.7(8) y
C14A C13A H13A 124.1 ?
C10 C13A H13A 124.1 ?
C13A C14A C15 111.2(8) y
C13A C14A H14A 124.4 ?
C15 C14A H14A 124.4 ?
C19 C15 C16 106.6(3) ?
C19 C15 C14 114.3(4) ?
C16 C15 C14 138.8(4) ?
C19 C15 C14A 152.5(5) ?
C16 C15 C14A 100.6(5) ?
C19 C15 Fe1 69.39(19) ?
C16 C15 Fe1 68.4(2) ?
C14 C15 Fe1 130.7(3) ?
C14A C15 Fe1 126.1(4) ?
C17 C16 C15 108.7(3) ?
C17 C16 Fe1 70.17(18) ?
C15 C16 Fe1 70.7(2) ?
C17 C16 H16 125.6 ?
C15 C16 H16 125.6 ?
Fe1 C16 H16 125.1 ?
C18 C17 C16 107.0(3) ?
C18 C17 Fe1 69.88(19) ?
C16 C17 Fe1 69.03(19) ?
C18 C17 H17 126.5 ?
C16 C17 H17 126.5 ?
Fe1 C17 H17 126.2 ?
C17 C18 C19 108.6(3) ?
C17 C18 Fe1 69.90(18) ?
C19 C18 Fe1 69.79(19) ?
C17 C18 H18 125.7 ?
C19 C18 H18 125.7 ?
Fe1 C18 H18 126.2 ?
C15 C19 C18 109.0(4) ?
C15 C19 Fe1 70.6(2) ?
C18 C19 Fe1 69.81(18) ?
C15 C19 H19 125.5 ?
C18 C19 H19 125.5 ?
Fe1 C19 H19 125.6 ?
C16 Fe1 C23 172.91(18) ?
C16 Fe1 C19 67.82(18) ?
C23 Fe1 C19 115.24(16) ?
C16 Fe1 C18 67.80(13) ?
C23 Fe1 C18 109.99(13) ?
C19 Fe1 C18 40.39(14) ?
C16 Fe1 C17 40.80(15) ?
C23 Fe1 C17 133.27(14) ?
C19 Fe1 C17 68.07(15) ?
C18 Fe1 C17 40.23(13) ?
C16 Fe1 C20 114.73(14) ?
C23 Fe1 C20 68.06(13) ?
C19 Fe1 C20 135.46(14) ?
C18 Fe1 C20 174.81(14) ?
C17 Fe1 C20 144.56(13) ?
C16 Fe1 C24 145.43(15) ?
C23 Fe1 C24 40.73(13) ?
C19 Fe1 C24 110.87(15) ?
C18 Fe1 C24 134.91(13) ?
C17 Fe1 C24 173.43(14) ?
C20 Fe1 C24 40.56(13) ?
C16 Fe1 C22 133.52(18) ?
C23 Fe1 C22 40.41(15) ?
C19 Fe1 C22 144.86(16) ?
C18 Fe1 C22 113.84(13) ?
C17 Fe1 C22 108.50(14) ?
C20 Fe1 C22 68.07(13) ?
C24 Fe1 C22 68.38(14) ?
C16 Fe1 C21 109.27(15) ?
C23 Fe1 C21 68.23(13) ?
C19 Fe1 C21 174.40(15) ?
C18 Fe1 C21 143.81(13) ?
C17 Fe1 C21 113.16(13) ?
C20 Fe1 C21 40.63(13) ?
C24 Fe1 C21 68.56(13) ?
C22 Fe1 C21 40.56(14) ?
C16 Fe1 C15 40.93(19) ?
C23 Fe1 C15 145.36(18) ?
C19 Fe1 C15 40.00(18) ?
C18 Fe1 C15 67.87(14) ?
C17 Fe1 C15 68.72(15) ?
C20 Fe1 C15 110.77(14) ?
C24 Fe1 C15 114.95(15) ?
C22 Fe1 C15 173.88(19) ?
C21 Fe1 C15 134.75(16) ?
C24 C20 C21 108.7(3) ?
C24 C20 Fe1 69.76(18) ?
C21 C20 Fe1 69.92(18) ?
C24 C20 H20 125.7 ?
C21 C20 H20 125.7 ?
Fe1 C20 H20 126.2 ?
C22 C21 C20 107.4(3) ?
C22 C21 Fe1 69.63(18) ?
C20 C21 Fe1 69.45(18) ?
C22 C21 H21 126.3 ?
C20 C21 H21 126.3 ?
Fe1 C21 H21 126.2 ?
C23 C22 C21 108.2(3) ?
C23 C22 Fe1 69.54(19) ?
C21 C22 Fe1 69.80(18) ?
C23 C22 H22 125.9 ?
C21 C22 H22 125.9 ?
Fe1 C22 H22 126.3 ?
C22 C23 C24 108.5(3) ?
C22 C23 Fe1 70.05(19) ?
C24 C23 Fe1 69.78(18) ?
C22 C23 H23 125.8 ?
C24 C23 H23 125.8 ?
Fe1 C23 H23 126.0 ?
C20 C24 C23 107.3(3) ?
C20 C24 Fe1 69.68(18) ?
C23 C24 Fe1 69.49(19) ?
C20 C24 H24 126.4 ?
C23 C24 H24 126.4 ?
Fe1 C24 H24 126.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 1.905(3) yes
C1 C6 1.368(4) ?
C1 C2 1.375(4) ?
C2 C3 1.381(4) ?
C2 H2 0.9500 ?
C3 C4 1.397(4) ?
C3 H3 0.9500 ?
C4 C5 1.391(4) ?
C4 C7 1.490(4) yes
C5 C6 1.389(5) ?
C5 H5 0.9500 ?
C6 H6 0.9500 ?
C7 C8 1.400(4) ?
C7 C12 1.400(5) ?
C8 C9 1.397(5) ?
C8 H8 0.9500 ?
C9 C10 1.403(7) y
C9 H9 0.9500 ?
C10 C11 1.385(7) y
C10 C13 1.506(7) y
C10 C13A 1.576(11) y
C11 C12 1.381(5) ?
C11 H11 0.9500 ?
C12 H12 0.9500 ?
C13 C14 1.309(10) y
C13 H13 0.9500 ?
C14 C15 1.509(7) y
C14 H14 0.9500 ?
C13A C14A 1.353(15) y
C13A H13A 0.9500 ?
C14A C15 1.539(9) y
C14A H14A 0.9500 ?
C15 C19 1.404(6) ?
C15 C16 1.431(7) ?
C15 Fe1 2.061(3) ?
C16 C17 1.421(5) ?
C16 Fe1 2.030(4) ?
C16 H16 0.9500 ?
C17 C18 1.407(5) ?
C17 Fe1 2.045(3) ?
C17 H17 0.9500 ?
C18 C19 1.412(5) ?
C18 Fe1 2.045(3) ?
C18 H18 0.9500 ?
C19 Fe1 2.045(3) ?
C19 H19 0.9500 ?
Fe1 C23 2.043(3) ?
Fe1 C20 2.045(3) ?
Fe1 C24 2.047(3) ?
Fe1 C22 2.049(3) ?
Fe1 C21 2.052(3) ?
C20 C24 1.418(5) ?
C20 C21 1.423(5) ?
C20 H20 0.9500 ?
C21 C22 1.422(5) ?
C21 H21 0.9500 ?
C22 C23 1.413(5) ?
C22 H22 0.9500 ?
C23 C24 1.423(5) ?
C23 H23 0.9500 ?
C24 H24 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C20 H20 Br1 0.95 2.92 3.588(3) 128.8 2_745
