#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/78/4077819.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_4077819
loop_
_publ_author_name
'Lentz, Dieter'
'Willemsen, Stefan'
_publ_section_title
;
 Coordination Chemistry of Fluorinated Allenes
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              3962
_journal_paper_doi               10.1021/om9904798
_journal_volume                  18
_journal_year                    1999
_chemical_formula_sum            'C10 H9 Mn O2'
_chemical_formula_weight         216.11
_chemical_melting_point          300.15
_chemical_name_systematic
; 
 Dicarbonyl(eta5-cyclopentadienyl)(eta2-propadien)manganese 
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.10(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.321(2)
_cell_length_b                   7.397(2)
_cell_length_c                   23.885(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      18.1
_cell_measurement_theta_min      8.3
_cell_volume                     1800.5(7)
_computing_cell_refinement       'ENRAF-NONIUS EXPRESS'
_computing_data_collection       'ENRAF-NONIUS EXPRESS'
_computing_data_reduction        'HELENA (Spek, 1996)'
_computing_molecular_graphics    'XPMA, ZORTEP (Zsolnai, 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'ENRAF-NONIUS CAD4'
_diffrn_measurement_method       omega-2theta-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3238
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.89
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  '7200 s'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.424
_exptl_absorpt_correction_type   no
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       leaflet
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.709
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       none
_refine_ls_extinction_expression none
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          15.000
_refine_ls_shift/su_mean         0.061
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0796P)²+5.0707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1621
_reflns_number_gt                2140
_reflns_number_total             3159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om9904798.cif
_cod_data_source_block           mnh
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '27 C' was changed to '300.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom, difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4077819
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
Mn1 Mn 0.19639(7) 0.20176(10) 0.11291(3) 0.0148(2) Uani 1 1 d .
C11 C 0.1538(5) 0.0071(7) 0.0688(2) 0.0184(11) Uani 1 1 d .
O11 O 0.1275(4) -0.1166(5) 0.04091(15) 0.0297(9) Uani 1 1 d .
C12 C 0.3477(5) 0.2138(7) 0.0858(2) 0.0234(12) Uani 1 1 d .
O12 O 0.4449(4) 0.2244(6) 0.06850(19) 0.0395(11) Uani 1 1 d .
C1R C 0.0206(4) 0.3001(5) 0.14179(16) 0.0304(13) Uani 1 1 d G
H1R H -0.0333 0.2318 0.1613 0.037 Uiso 1 1 calc R
C2R C 0.1310(4) 0.4034(6) 0.16650(13) 0.0384(16) Uani 1 1 d G
H2R H 0.1621 0.4145 0.2051 0.046 Uiso 1 1 calc R
C3R C 0.1855(3) 0.4866(5) 0.1220(2) 0.0469(19) Uani 1 1 d G
H3R H 0.2586 0.5619 0.1263 0.056 Uiso 1 1 calc R
C4R C 0.1089(4) 0.4348(6) 0.06975(15) 0.0381(16) Uani 1 1 d G
H4R H 0.1229 0.4702 0.0338 0.046 Uiso 1 1 calc R
C5R C 0.0069(4) 0.3196(6) 0.08200(15) 0.0346(14) Uani 1 1 d G
H5R H -0.0575 0.2662 0.0555 0.042 Uiso 1 1 calc R
C2 C 0.3228(5) 0.1222(7) 0.1826(2) 0.0211(11) Uani 1 1 d .
C3 C 0.4324(6) 0.1846(9) 0.2123(2) 0.0311(13) Uani 1 1 d .
C1 C 0.2234(6) -0.0041(8) 0.1765(2) 0.0240(12) Uani 1 1 d .
H31 H 0.474(6) 0.123(10) 0.252(2) 0.042(18) Uiso 1 1 d .
H32 H 0.482(8) 0.282(11) 0.204(3) 0.06(2) Uiso 1 1 d .
H12 H 0.234(5) -0.120(9) 0.166(2) 0.023(15) Uiso 1 1 d .
H11 H 0.157(6) -0.019(8) 0.203(2) 0.031(16) Uiso 1 1 d .
Mn2 Mn 0.69634(7) 0.70811(11) 0.11618(3) 0.0202(3) Uani 1 1 d .
C21 C 0.6877(5) 0.5455(8) 0.0607(2) 0.0257(12) Uani 1 1 d .
O21 O 0.6856(4) 0.4392(6) 0.02532(16) 0.0368(10) Uani 1 1 d .
C22 C 0.7260(6) 0.5170(8) 0.1654(2) 0.0295(13) Uani 1 1 d .
O22 O 0.7565(5) 0.4050(8) 0.1973(2) 0.0579(14) Uani 1 1 d .
C21R C 0.8935(3) 0.8064(5) 0.13105(15) 0.0256(12) Uani 1 1 d G
H21R H 0.9671 0.7330 0.1392 0.031 Uiso 1 1 calc R
C22R C 0.8330(4) 0.8620(6) 0.07620(12) 0.0281(13) Uani 1 1 d G
H22R H 0.8602 0.8314 0.0421 0.034 Uiso 1 1 calc R
C23R C 0.7238(3) 0.9727(6) 0.08252(14) 0.0336(14) Uani 1 1 d G
H23R H 0.6669 1.0272 0.0533 0.040 Uiso 1 1 calc R
C24R C 0.7168(3) 0.9854(5) 0.14128(16) 0.0334(14) Uani 1 1 d G
H24R H 0.6544 1.0497 0.1573 0.040 Uiso 1 1 calc R
C25R C 0.8216(4) 0.8827(6) 0.17128(11) 0.0280(12) Uani 1 1 d G
H25R H 0.8400 0.8679 0.2104 0.034 Uiso 1 1 calc R
C5 C 0.5340(7) 0.6950(10) 0.1538(3) 0.0479(18) Uani 1 1 d .
C6 C 0.5103(7) 0.6846(9) 0.2058(3) 0.0330(14) Uani 1 1 d .
C4 C 0.4944(7) 0.7240(11) 0.0938(3) 0.0439(17) Uani 1 1 d .
H41 H 0.406(4) 0.791(6) 0.0746(17) 0.000(10) Uiso 1 1 d .
H42 H 0.446(7) 0.599(10) 0.072(3) 0.050(19) Uiso 1 1 d .
H61 H 0.567(10) 0.672(14) 0.239(4) 0.10(4) Uiso 1 1 d .
H62 H 0.432(10) 0.695(14) 0.215(4) 0.11(4) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 '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
C12 Mn1 C11 88.5(2) ?
C12 Mn1 C2 80.0(2) ?
C11 Mn1 C2 108.3(2) ?
C12 Mn1 C3R 92.9(2) ?
C11 Mn1 C3R 147.4(2) ?
C2 Mn1 C3R 104.0(2) ?
C12 Mn1 C4R 96.5(2) ?
C11 Mn1 C4R 108.6(2) ?
C2 Mn1 C4R 142.8(2) ?
C3R Mn1 C4R 38.96(7) ?
C12 Mn1 C1 105.7(2) ?
C11 Mn1 C1 80.7(2) ?
C2 Mn1 C1 38.5(2) ?
C3R Mn1 C1 129.6(2) ?
C4R Mn1 C1 156.36(19) ?
C12 Mn1 C2R 123.9(2) ?
C11 Mn1 C2R 146.82(19) ?
C2 Mn1 C2R 86.25(18) ?
C3R Mn1 C2R 38.88(7) ?
C4R Mn1 C2R 64.98(8) ?
C1 Mn1 C2R 95.1(2) ?
C12 Mn1 C5R 130.7(2) ?
C11 Mn1 C5R 89.92(18) ?
C2 Mn1 C5R 145.63(18) ?
C3R Mn1 C5R 64.85(8) ?
C4R Mn1 C5R 38.60(6) ?
C1 Mn1 C5R 122.6(2) ?
C2R Mn1 C5R 64.53(8) ?
C12 Mn1 C1R 157.5(2) ?
C11 Mn1 C1R 108.45(19) ?
C2 Mn1 C1R 107.34(18) ?
C3R Mn1 C1R 64.77(8) ?
C4R Mn1 C1R 64.58(8) ?
C1 Mn1 C1R 91.98(19) ?
C2R Mn1 C1R 38.48(6) ?
C5R Mn1 C1R 38.31(6) ?
O11 C11 Mn1 179.6(5) ?
O12 C12 Mn1 178.9(5) ?
C2R C1R C5R 108.0 ?
C2R C1R Mn1 69.87(15) ?
C5R C1R Mn1 70.66(15) ?
C2R C1R H1R 126.0 ?
C5R C1R H1R 126.0 ?
Mn1 C1R H1R 125.1 ?
C3R C2R C1R 108.0 ?
C3R C2R Mn1 69.81(15) ?
C1R C2R Mn1 71.66(15) ?
C3R C2R H2R 126.0 ?
C1R C2R H2R 126.0 ?
Mn1 C2R H2R 124.1 ?
C2R C3R C4R 108.0 ?
C2R C3R Mn1 71.31(15) ?
C4R C3R Mn1 70.96(15) ?
C2R C3R H3R 126.0 ?
C4R C3R H3R 126.0 ?
Mn1 C3R H3R 123.4 ?
C3R C4R C5R 108.0 ?
C3R C4R Mn1 70.08(16) ?
C5R C4R Mn1 71.72(15) ?
C3R C4R H4R 126.0 ?
C5R C4R H4R 126.0 ?
Mn1 C4R H4R 123.8 ?
C4R C5R C1R 108.0 ?
C4R C5R Mn1 69.69(15) ?
C1R C5R Mn1 71.03(15) ?
C4R C5R H5R 126.0 ?
C1R C5R H5R 126.0 ?
Mn1 C5R H5R 124.9 ?
C3 C2 C1 148.6(5) y
C3 C2 Mn1 136.4(5) ?
C1 C2 Mn1 74.9(3) ?
C2 C3 H31 121(4) ?
C2 C3 H32 128(5) ?
H31 C3 H32 111(6) ?
C2 C1 Mn1 66.6(3) ?
C2 C1 H12 124(4) ?
Mn1 C1 H12 119(3) ?
C2 C1 H11 125(3) ?
Mn1 C1 H11 120(3) ?
H12 C1 H11 101(5) ?
C21 Mn2 C22 86.6(3) ?
C21 Mn2 C5 110.5(3) ?
C22 Mn2 C5 75.2(3) ?
C21 Mn2 C4 85.2(2) ?
C22 Mn2 C4 105.6(3) ?
C5 Mn2 C4 41.3(3) ?
C21 Mn2 C25R 145.43(19) ?
C22 Mn2 C25R 92.7(2) ?
C5 Mn2 C25R 102.6(2) ?
C4 Mn2 C25R 127.8(2) ?
C21 Mn2 C21R 106.73(19) ?
C22 Mn2 C21R 95.6(2) ?
C5 Mn2 C21R 140.8(2) ?
C4 Mn2 C21R 156.4(3) ?
C25R Mn2 C21R 38.89(6) ?
C21 Mn2 C24R 147.9(2) ?
C22 Mn2 C24R 124.1(2) ?
C5 Mn2 C24R 88.5(2) ?
C4 Mn2 C24R 93.9(2) ?
C25R Mn2 C24R 38.88(6) ?
C21R Mn2 C24R 65.03(8) ?
C21 Mn2 C22R 89.21(19) ?
C22 Mn2 C22R 129.7(2) ?
C5 Mn2 C22R 150.4(2) ?
C4 Mn2 C22R 124.0(2) ?
C25R Mn2 C22R 64.94(8) ?
C21R Mn2 C22R 38.69(6) ?
C24R Mn2 C22R 64.79(8) ?
C21 Mn2 C23R 109.3(2) ?
C22 Mn2 C23R 157.3(2) ?
C5 Mn2 C23R 112.1(2) ?
C4 Mn2 C23R 92.2(2) ?
C25R Mn2 C23R 64.93(8) ?
C21R Mn2 C23R 64.80(8) ?
C24R Mn2 C23R 38.66(7) ?
C22R Mn2 C23R 38.55(6) ?
O21 C21 Mn2 178.1(5) ?
O22 C22 Mn2 173.3(6) ?
C22R C21R C25R 108.0 ?
C22R C21R Mn2 71.18(15) ?
C25R C21R Mn2 70.26(15) ?
C22R C21R H21R 126.0 ?
C25R C21R H21R 126.0 ?
Mn2 C21R H21R 124.2 ?
C21R C22R C23R 108.0 ?
C21R C22R Mn2 70.13(15) ?
C23R C22R Mn2 70.76(15) ?
C21R C22R H22R 126.0 ?
C23R C22R H22R 126.0 ?
Mn2 C22R H22R 124.7 ?
C22R C23R C24R 108.0 ?
C22R C23R Mn2 70.69(15) ?
C24R C23R Mn2 70.16(14) ?
C22R C23R H23R 126.0 ?
C24R C23R H23R 126.0 ?
Mn2 C23R H23R 124.7 ?
C25R C24R C23R 108.0 ?
C25R C24R Mn2 70.22(15) ?
C23R C24R Mn2 71.17(14) ?
C25R C24R H24R 126.0 ?
C23R C24R H24R 126.0 ?
Mn2 C24R H24R 124.2 ?
C24R C25R C21R 108.0 ?
C24R C25R Mn2 70.91(15) ?
C21R C25R Mn2 70.85(15) ?
C24R C25R H25R 126.0 ?
C21R C25R H25R 126.0 ?
Mn2 C25R H25R 123.9 ?
C6 C5 C4 152.6(7) y
C6 C5 Mn2 135.9(6) ?
C4 C5 Mn2 71.1(4) ?
C5 C6 H61 130(6) ?
C5 C6 H62 123(7) ?
H61 C6 H62 107(9) ?
C5 C4 Mn2 67.7(4) ?
C5 C4 H41 125(2) ?
Mn2 C4 H41 152(2) ?
C5 C4 H42 112(3) ?
Mn2 C4 H42 115(3) ?
H41 C4 H42 84(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Mn1 C12 1.784(5) y
Mn1 C11 1.798(5) y
Mn1 C2 2.032(5) y
Mn1 C3R 2.123(4) ?
Mn1 C4R 2.135(4) ?
Mn1 C1 2.138(5) y
Mn1 C2R 2.143(4) ?
Mn1 C5R 2.161(4) ?
Mn1 C1R 2.166(4) ?
C11 O11 1.138(6) ?
C12 O12 1.147(7) ?
C1R C2R 1.4200 ?
C1R C5R 1.4200 ?
C1R H1R 0.9300 ?
C2R C3R 1.4200 ?
C2R H2R 0.9300 ?
C3R C4R 1.4200 ?
C3R H3R 0.9300 ?
C4R C5R 1.4200 ?
C4R H4R 0.9300 ?
C5R H5R 0.9300 ?
C2 C3 1.320(8) y
C2 C1 1.378(8) y
C3 H31 1.08(6) ?
C3 H32 0.92(8) ?
C1 H12 0.90(6) ?
C1 H11 1.00(6) ?
Mn2 C21 1.782(6) y
Mn2 C22 1.834(6) y
Mn2 C5 2.026(7) y
Mn2 C4 2.071(7) y
Mn2 C25R 2.129(4) ?
Mn2 C21R 2.137(4) ?
Mn2 C24R 2.138(4) ?
Mn2 C22R 2.150(4) ?
Mn2 C23R 2.151(4) ?
C21 O21 1.152(7) ?
C22 O22 1.136(7) ?
C21R C22R 1.4200 ?
C21R C25R 1.4200 ?
C21R H21R 0.9300 ?
C22R C23R 1.4200 ?
C22R H22R 0.9300 ?
C23R C24R 1.4200 ?
C23R H23R 0.9300 ?
C24R C25R 1.4200 ?
C24R H24R 0.9300 ?
C25R H25R 0.9300 ?
C5 C6 1.305(9) y
C5 C4 1.444(9) y
C6 H61 0.91(10) ?
C6 H62 0.87(10) ?
C4 H41 1.07(4) ?
C4 H42 1.14(7) ?
