#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/16/4071646.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_4071646
loop_
_publ_author_name
'Banide, Emilie V.'
'Ortin, Yannick'
'Chamiot, Bénédicte'
'Cassidy, Andrew'
'Niehaus, Jan'
'Moore, Angela'
'Seward, Corey M.'
'Müller-Bunz, Helge'
'McGlinchey, Michael J.'
_publ_section_title
;
 Syntheses, Structures, and Dimerizations of Ferrocenyl- and
 Fluorenylideneallenes: Push−Pull Multiple Bonds?
;
_journal_issue                   16
_journal_name_full               Organometallics
_journal_page_first              4173
_journal_paper_doi               10.1021/om800293m
_journal_volume                  27
_journal_year                    2008
_chemical_formula_moiety         'C22 H16 O2'
_chemical_formula_sum            'C22 H16 O2'
_chemical_formula_weight         312.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 94.393(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.353(3)
_cell_length_b                   4.2632(6)
_cell_length_c                   16.519(2)
_cell_measurement_reflns_used    2553
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.62
_cell_measurement_theta_min      2.47
_cell_volume                     1569.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7922
_diffrn_reflns_theta_full        21.97
_diffrn_reflns_theta_max         21.97
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.8489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             656
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.102
_refine_diff_density_min         -0.087
_refine_diff_density_rms         0.023
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         1928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0458P)²+0.2144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0849
_reflns_number_gt                1614
_reflns_number_total             1928
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800293m-file002.cif
_cod_data_source_block           mjm78
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1569.5(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4071646
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.36575(8) 0.1535(4) 0.28239(10) 0.0571(5) Uani 1 1 d .
H1 H 0.3388 0.1259 0.2372 0.069 Uiso 1 1 calc R
C2 C 0.42218(8) 0.0184(4) 0.28527(11) 0.0624(5) Uani 1 1 d .
H2 H 0.4334 -0.0976 0.2412 0.075 Uiso 1 1 calc R
C3 C 0.46198(8) 0.0538(4) 0.35265(11) 0.0625(5) Uani 1 1 d .
H3 H 0.4998 -0.0381 0.3536 0.075 Uiso 1 1 calc R
C4 C 0.44618(8) 0.2245(4) 0.41877(10) 0.0568(5) Uani 1 1 d .
H4 H 0.4728 0.2453 0.4646 0.068 Uiso 1 1 calc R
C4A C 0.39058(7) 0.3634(4) 0.41590(9) 0.0472(4) Uani 1 1 d .
C4B C 0.36260(7) 0.5619(4) 0.47482(9) 0.0483(4) Uani 1 1 d .
C5 C 0.38479(8) 0.6641(4) 0.55049(10) 0.0580(5) Uani 1 1 d .
H5 H 0.4223 0.5979 0.5723 0.070 Uiso 1 1 calc R
C6 C 0.35070(9) 0.8659(4) 0.59332(11) 0.0633(5) Uani 1 1 d .
H6 H 0.3652 0.9363 0.6444 0.076 Uiso 1 1 calc R
C7 C 0.29542(8) 0.9630(4) 0.56061(10) 0.0622(5) Uani 1 1 d .
H7 H 0.2734 1.1040 0.5894 0.075 Uiso 1 1 calc R
C8 C 0.27181(8) 0.8560(4) 0.48600(10) 0.0578(5) Uani 1 1 d .
H8 H 0.2340 0.9206 0.4652 0.069 Uiso 1 1 calc R
C8A C 0.30543(7) 0.6500(4) 0.44235(9) 0.0480(4) Uani 1 1 d .
C9 C 0.29407(7) 0.5015(4) 0.36150(9) 0.0496(4) Uani 1 1 d .
C9A C 0.35011(7) 0.3299(4) 0.34762(9) 0.0472(4) Uani 1 1 d .
C10 C 0.24621(7) 0.5115(4) 0.30746(10) 0.0570(5) Uani 1 1 d .
H10 H 0.2508 0.4182 0.2574 0.068 Uiso 1 1 calc R
C11 C 0.18696(8) 0.6532(5) 0.31790(11) 0.0634(5) Uani 1 1 d .
O1 O 0.16518(6) 0.6368(4) 0.38379(8) 0.0912(5) Uani 1 1 d .
C12 C 0.15389(7) 0.8078(4) 0.24841(10) 0.0544(5) Uani 1 1 d .
C13 C 0.17714(7) 0.8528(4) 0.17431(10) 0.0582(5) Uani 1 1 d .
H13 H 0.2158 0.7831 0.1674 0.070 Uiso 1 1 calc R
C14 C 0.14514(7) 0.9971(4) 0.11012(11) 0.0603(5) Uani 1 1 d .
H14 H 0.1620 1.0235 0.0608 0.072 Uiso 1 1 calc R
C15 C 0.08792(8) 1.1017(4) 0.11977(11) 0.0624(5) Uani 1 1 d .
O2 O 0.05158(6) 1.2444(4) 0.06172(8) 0.0838(5) Uani 1 1 d .
C18 C 0.07290(10) 1.2897(6) -0.01628(12) 0.0896(7) Uani 1 1 d .
H18A H 0.1080 1.4200 -0.0115 0.134 Uiso 1 1 calc R
H18B H 0.0423 1.3895 -0.0513 0.134 Uiso 1 1 calc R
H18C H 0.0828 1.0904 -0.0388 0.134 Uiso 1 1 calc R
C16 C 0.06381(8) 1.0618(5) 0.19414(12) 0.0789(6) Uani 1 1 d .
H16 H 0.0252 1.1331 0.2011 0.095 Uiso 1 1 calc R
C17 C 0.09622(8) 0.9192(5) 0.25681(12) 0.0731(6) Uani 1 1 d .
H17 H 0.0795 0.8957 0.3063 0.088 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
C9A C1 C2 118.97(16)
C9A C1 H1 120.5
C2 C1 H1 120.5
C3 C2 C1 120.81(17)
C3 C2 H2 119.6
C1 C2 H2 119.6
C2 C3 C4 120.52(17)
C2 C3 H3 119.7
C4 C3 H3 119.7
C4A C4 C3 119.03(16)
C4A C4 H4 120.5
C3 C4 H4 120.5
C4 C4A C9A 120.76(15)
C4 C4A C4B 131.05(15)
C9A C4A C4B 108.18(14)
C5 C4B C8A 121.14(16)
C5 C4B C4A 129.94(16)
C8A C4B C4A 108.91(14)
C4B C5 C6 119.15(17)
C4B C5 H5 120.4
C6 C5 H5 120.4
C7 C6 C5 120.10(17)
C7 C6 H6 119.9
C5 C6 H6 119.9
C6 C7 C8 121.48(18)
C6 C7 H7 119.3
C8 C7 H7 119.3
C7 C8 C8A 119.09(17)
C7 C8 H8 120.5
C8A C8 H8 120.5
C8 C8A C4B 118.95(15)
C8 C8A C9 132.37(15)
C4B C8A C9 108.63(14)
C10 C9 C8A 131.25(16)
C10 C9 C9A 123.58(15)
C8A C9 C9A 105.15(13)
C1 C9A C4A 119.89(15)
C1 C9A C9 131.02(15)
C4A C9A C9 109.08(14)
C9 C10 C11 127.74(16)
C9 C10 H10 116.1
C11 C10 H10 116.1
O1 C11 C12 120.46(17)
O1 C11 C10 119.99(16)
C12 C11 C10 119.53(15)
C13 C12 C17 117.14(16)
C13 C12 C11 123.58(15)
C17 C12 C11 119.27(16)
C14 C13 C12 122.43(16)
C14 C13 H13 118.8
C12 C13 H13 118.8
C15 C14 C13 119.23(16)
C15 C14 H14 120.4
C13 C14 H14 120.4
O2 C15 C14 125.24(16)
O2 C15 C16 115.42(16)
C14 C15 C16 119.34(17)
C15 O2 C18 118.62(14)
O2 C18 H18A 109.5
O2 C18 H18B 109.5
H18A C18 H18B 109.5
O2 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C17 C16 C15 120.50(17)
C17 C16 H16 119.8
C15 C16 H16 119.8
C16 C17 C12 121.36(17)
C16 C17 H17 119.3
C12 C17 H17 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C9A 1.381(2)
C1 C2 1.384(2)
C1 H1 0.9300
C2 C3 1.379(2)
C2 H2 0.9300
C3 C4 1.381(2)
C3 H3 0.9300
C4 C4A 1.374(2)
C4 H4 0.9300
C4A C9A 1.398(2)
C4A C4B 1.466(2)
C4B C5 1.380(2)
C4B C8A 1.399(2)
C5 C6 1.380(2)
C5 H5 0.9300
C6 C7 1.374(2)
C6 H6 0.9300
C7 C8 1.381(2)
C7 H7 0.9300
C8 C8A 1.393(2)
C8 H8 0.9300
C8A C9 1.482(2)
C9 C10 1.340(2)
C9 C9A 1.484(2)
C10 C11 1.478(2)
C10 H10 0.9300
C11 O1 1.2277(19)
C11 C12 1.473(2)
C12 C13 1.379(2)
C12 C17 1.390(2)
C13 C14 1.378(2)
C13 H13 0.9300
C14 C15 1.375(2)
C14 H14 0.9300
C15 O2 1.353(2)
C15 C16 1.389(2)
O2 C18 1.421(2)
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C16 C17 1.361(3)
C16 H16 0.9300
C17 H17 0.9300
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
C9A C1 C2 C3 1.2(2)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C4A -1.1(2)
C3 C4 C4A C9A 0.8(2)
C3 C4 C4A C4B -178.12(15)
C4 C4A C4B C5 -0.2(3)
C9A C4A C4B C5 -179.23(15)
C4 C4A C4B C8A 178.76(15)
C9A C4A C4B C8A -0.25(17)
C8A C4B C5 C6 -2.4(2)
C4A C4B C5 C6 176.48(15)
C4B C5 C6 C7 -0.1(3)
C5 C6 C7 C8 1.9(3)
C6 C7 C8 C8A -1.3(3)
C7 C8 C8A C4B -1.1(2)
C7 C8 C8A C9 -178.19(16)
C5 C4B C8A C8 3.0(2)
C4A C4B C8A C8 -176.12(13)
C5 C4B C8A C9 -179.30(14)
C4A C4B C8A C9 1.61(17)
C8 C8A C9 C10 -3.4(3)
C4B C8A C9 C10 179.26(16)
C8 C8A C9 C9A 175.03(16)
C4B C8A C9 C9A -2.28(16)
C2 C1 C9A C4A -1.5(2)
C2 C1 C9A C9 179.61(15)
C4 C4A C9A C1 0.5(2)
C4B C4A C9A C1 179.66(14)
C4 C4A C9A C9 179.65(14)
C4B C4A C9A C9 -1.22(16)
C10 C9 C9A C1 -0.3(3)
C8A C9 C9A C1 -178.88(16)
C10 C9 C9A C4A -179.26(15)
C8A C9 C9A C4A 2.14(16)
C8A C9 C10 C11 -7.1(3)
C9A C9 C10 C11 174.68(16)
C9 C10 C11 O1 -36.9(3)
C9 C10 C11 C12 144.33(18)
O1 C11 C12 C13 175.64(17)
C10 C11 C12 C13 -5.6(3)
O1 C11 C12 C17 -3.7(3)
C10 C11 C12 C17 175.05(17)
C17 C12 C13 C14 -0.9(3)
C11 C12 C13 C14 179.72(17)
C12 C13 C14 C15 0.2(3)
C13 C14 C15 O2 -179.43(18)
C13 C14 C15 C16 0.5(3)
C14 C15 O2 C18 0.7(3)
C16 C15 O2 C18 -179.20(19)
O2 C15 C16 C17 179.56(19)
C14 C15 C16 C17 -0.4(3)
C15 C16 C17 C12 -0.4(3)
C13 C12 C17 C16 1.0(3)
C11 C12 C17 C16 -179.56(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659772
