#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/97/7019705.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_7019705
loop_
_publ_author_name
'Palomas, David'
'Holle, Sigrid'
'Inés, Blanca'
'Bruns, Hans'
'Goddard, Richard'
'Alcarazo, Manuel'
_publ_section_title
;
 Synthesis and reactivity of electron poor allenes: formation of
 completely organic frustrated Lewis pairs.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9073
_journal_page_last               9082
_journal_paper_doi               10.1039/c2dt30195d
_journal_volume                  41
_journal_year                    2012
_chemical_compound_source        hexane
_chemical_formula_moiety         'C28 H24 F2 O4 S'
_chemical_formula_sum            'C28 H24 F2 O4 S'
_chemical_formula_weight         494.53
_chemical_name_systematic
;
1-(3,5-difluoro-9H-fluoren-9-ylidene)-1-(4-(methyl)phenylthio)-
2,2-di(ethoxycarbonyl)-ethane
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_block_code                HOS-HG-043-03
_audit_creation_date             2012-01-18
_cell_angle_alpha                98.06(2)
_cell_angle_beta                 104.24(2)
_cell_angle_gamma                105.687(12)
_cell_formula_units_Z            2
_cell_length_a                   7.9304(17)
_cell_length_b                   12.5572(16)
_cell_length_c                   13.327(4)
_cell_measurement_reflns_used    23288
_cell_measurement_temperature    200
_cell_measurement_theta_max      28.0412
_cell_measurement_theta_min      2.6049
_cell_volume                     1207.7(5)
_computing_cell_refinement       'DENZO (Bruker AXS, 2006)'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'DENZO (Bruker AXS, 2006)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21411
_diffrn_reflns_theta_full        28.16
_diffrn_reflns_theta_max         28.16
_diffrn_reflns_theta_min         2.61
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.97247
_exptl_absorpt_correction_T_min  0.95082
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0536P)²+0.4692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                4668
_reflns_number_total             5879
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt30195d.txt
_cod_data_source_block           7080_39
_cod_original_sg_symbol_Hall     '-p 1'
_cod_original_sg_symbol_H-M      'p -1'
_cod_database_code               7019705
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
C1 C 0.2978(2) 0.18024(13) 0.25732(13) 0.0302(3) Uani 1 1 d .
C2 C 0.3019(2) 0.10241(13) 0.17697(13) 0.0295(3) Uani 1 1 d .
C3 C 0.2579(2) 0.10388(13) 0.06214(13) 0.0309(3) Uani 1 1 d .
C4 C 0.2047(2) 0.18079(14) 0.00566(14) 0.0385(4) Uani 1 1 d .
H4 H 0.2037 0.2510 0.0424 0.046 Uiso 1 1 calc R
C5 C 0.1532(3) 0.15431(16) -0.10446(15) 0.0446(4) Uani 1 1 d .
H5 H 0.1165 0.2060 -0.1437 0.054 Uiso 1 1 calc R
C6 C 0.1561(3) 0.05235(16) -0.15598(14) 0.0442(4) Uani 1 1 d .
C7 C 0.2053(2) -0.02745(15) -0.10499(14) 0.0411(4) Uani 1 1 d .
H7 H 0.2052 -0.0973 -0.1430 0.049 Uiso 1 1 calc R
C8 C 0.2550(2) -0.00036(13) 0.00519(13) 0.0328(3) Uani 1 1 d .
C9 C 0.3094(2) -0.06761(13) 0.08074(14) 0.0327(3) Uani 1 1 d .
C10 C 0.3373(3) -0.17240(14) 0.06186(16) 0.0422(4) Uani 1 1 d .
H10 H 0.3128 -0.2143 -0.0081 0.051 Uiso 1 1 calc R
C11 C 0.4019(3) -0.21198(14) 0.14935(18) 0.0468(5) Uani 1 1 d .
C12 C 0.4439(3) -0.15292(16) 0.25240(17) 0.0472(5) Uani 1 1 d .
H12 H 0.4924 -0.1831 0.3103 0.057 Uiso 1 1 calc R
C13 C 0.4143(3) -0.04829(15) 0.27043(16) 0.0387(4) Uani 1 1 d .
C14 C 0.3410(2) -0.00647(13) 0.18397(13) 0.0313(3) Uani 1 1 d .
C15 C 0.5068(2) 0.37069(13) 0.20896(13) 0.0317(3) Uani 1 1 d .
C16 C 0.5144(3) 0.45845(15) 0.15581(15) 0.0412(4) Uani 1 1 d .
H16 H 0.4098 0.4824 0.1347 0.049 Uiso 1 1 calc R
C17 C 0.6744(3) 0.51132(16) 0.13344(16) 0.0453(4) Uani 1 1 d .
H17 H 0.6785 0.5721 0.0979 0.054 Uiso 1 1 calc R
C18 C 0.8283(3) 0.47706(15) 0.16207(14) 0.0405(4) Uani 1 1 d .
C19 C 0.8170(2) 0.38718(15) 0.21308(14) 0.0394(4) Uani 1 1 d .
H19 H 0.9201 0.3613 0.2318 0.047 Uiso 1 1 calc R
C20 C 0.6593(2) 0.33456(14) 0.23715(14) 0.0366(4) Uani 1 1 d .
H20 H 0.6553 0.2739 0.2728 0.044 Uiso 1 1 calc R
C21 C 1.0046(3) 0.5375(2) 0.14119(19) 0.0587(6) Uani 1 1 d .
H21C H 1.0875 0.5927 0.2057 0.088 Uiso 1 1 calc R
H21B H 0.9774 0.5771 0.0838 0.088 Uiso 1 1 calc R
H21A H 1.0631 0.4821 0.1205 0.088 Uiso 1 1 calc R
C22 C 0.2868(2) 0.15571(13) 0.36377(13) 0.0307(3) Uani 1 1 d .
C23 C 0.1283(2) 0.18213(14) 0.39575(13) 0.0345(3) Uani 1 1 d .
C24 C -0.0220(3) 0.1613(2) 0.53027(19) 0.0585(6) Uani 1 1 d .
H24B H -0.0754 0.0938 0.5564 0.070 Uiso 1 1 calc R
H24A H -0.1219 0.1732 0.4764 0.070 Uiso 1 1 calc R
C25 C 0.0611(4) 0.2618(3) 0.6195(2) 0.0776(8) Uani 1 1 d .
H25A H 0.1002 0.3300 0.5922 0.116 Uiso 1 1 calc R
H25B H 0.1676 0.2530 0.6692 0.116 Uiso 1 1 calc R
H25C H -0.0295 0.2691 0.6563 0.116 Uiso 1 1 calc R
C26 C 0.4649(2) 0.21754(15) 0.45271(14) 0.0369(4) Uani 1 1 d .
C27 C 0.6370(3) 0.39282(19) 0.57742(18) 0.0613(6) Uani 1 1 d .
H27A H 0.6971 0.3453 0.6171 0.074 Uiso 1 1 calc R
H27B H 0.6063 0.4443 0.6283 0.074 Uiso 1 1 calc R
C28 C 0.7648(3) 0.4608(2) 0.5278(2) 0.0727(7) Uani 1 1 d .
H28A H 0.8057 0.4100 0.4835 0.109 Uiso 1 1 calc R
H28C H 0.8714 0.5142 0.5835 0.109 Uiso 1 1 calc R
H28B H 0.7017 0.5029 0.4838 0.109 Uiso 1 1 calc R
F1 F 0.10691(19) 0.02998(11) -0.26445(9) 0.0625(4) Uani 1 1 d .
F2 F 0.4324(2) -0.31451(9) 0.13448(12) 0.0670(4) Uani 1 1 d .
O1 O 0.02872(18) 0.22809(11) 0.35009(11) 0.0451(3) Uani 1 1 d .
O2 O 0.11696(18) 0.14239(12) 0.48249(10) 0.0449(3) Uani 1 1 d .
O3 O 0.5829(2) 0.17723(15) 0.48079(13) 0.0675(5) Uani 1 1 d .
O4 O 0.46893(19) 0.32026(12) 0.49582(12) 0.0553(4) Uani 1 1 d .
S1 S 0.30347(6) 0.31989(3) 0.24586(4) 0.03534(12) Uani 1 1 d .
H22 H 0.267(2) 0.0780(16) 0.3629(14) 0.032(5) Uiso 1 1 d .
H13 H 0.450(3) -0.0069(18) 0.3406(18) 0.049(6) 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
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 -1.00 0.0700
0.00 -1.00 1.00 0.1000
0.00 -1.00 -1.00 0.1300
0.00 1.00 1.00 0.1400
1.00 -1.00 -1.00 0.1200
-1.00 1.00 1.00 0.1100
3.00 -1.00 -1.00 0.1300
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
C2 C1 C22 123.33(14) y
C2 C1 S1 122.65(13) y
C22 C1 S1 114.03(11) y
C1 C2 C3 127.53(14) y
C1 C2 C14 127.36(15) y
C3 C2 C14 105.03(13) y
C4 C3 C8 118.73(15) y
C4 C3 C2 132.28(15) y
C8 C3 C2 108.61(14) y
C5 C4 C3 119.73(17) y
C5 C4 H4 120.1 n
C3 C4 H4 120.1 n
C6 C5 C4 119.14(18) y
C6 C5 H5 120.4 n
C4 C5 H5 120.4 n
F1 C6 C5 117.42(18) y
F1 C6 C7 118.66(18) y
C5 C6 C7 123.92(17) y
C6 C7 C8 116.39(17) y
C6 C7 H7 121.8 n
C8 C7 H7 121.8 n
C7 C8 C3 122.06(16) y
C7 C8 C9 129.25(16) y
C3 C8 C9 108.69(14) y
C10 C9 C14 121.99(16) y
C10 C9 C8 129.21(16) y
C14 C9 C8 108.73(14) y
C11 C10 C9 116.57(17) y
C11 C10 H10 121.7 n
C9 C10 H10 121.7 n
C10 C11 F2 118.54(18) y
C10 C11 C12 123.80(16) y
F2 C11 C12 117.63(18) y
C11 C12 C13 119.14(18) y
C11 C12 H12 120.4 n
C13 C12 H12 120.4 n
C12 C13 C14 119.28(18) y
C12 C13 H13 118.4(13) y
C14 C13 H13 122.2(13) y
C13 C14 C9 119.06(15) y
C13 C14 C2 131.95(15) y
C9 C14 C2 108.70(14) y
C16 C15 C20 119.33(16) y
C16 C15 S1 116.07(13) y
C20 C15 S1 124.39(13) y
C15 C16 C17 120.21(17) y
C15 C16 H16 119.9 n
C17 C16 H16 119.9 n
C18 C17 C16 121.14(17) y
C18 C17 H17 119.4 n
C16 C17 H17 119.4 n
C17 C18 C19 117.93(17) y
C17 C18 C21 121.04(18) y
C19 C18 C21 121.01(18) y
C20 C19 C18 121.60(17) y
C20 C19 H19 119.2 n
C18 C19 H19 119.2 n
C19 C20 C15 119.77(16) y
C19 C20 H20 120.1 n
C15 C20 H20 120.1 n
C18 C21 H21C 109.5 n
C18 C21 H21B 109.5 n
H21C C21 H21B 109.5 n
C18 C21 H21A 109.5 n
H21C C21 H21A 109.5 n
H21B C21 H21A 109.5 n
C1 C22 C23 113.44(14) y
C1 C22 C26 112.54(14) y
C23 C22 C26 109.05(13) y
C1 C22 H22 110.9(11) y
C23 C22 H22 105.4(11) y
C26 C22 H22 104.9(11) y
O1 C23 O2 125.90(16) y
O1 C23 C22 126.29(16) y
O2 C23 C22 107.80(14) y
O2 C24 C25 109.9(2) y
O2 C24 H24B 109.7 n
C25 C24 H24B 109.7 n
O2 C24 H24A 109.7 n
C25 C24 H24A 109.7 n
H24B C24 H24A 108.2 n
C24 C25 H25A 109.5 n
C24 C25 H25B 109.5 n
H25A C25 H25B 109.5 n
C24 C25 H25C 109.5 n
H25A C25 H25C 109.5 n
H25B C25 H25C 109.5 n
O3 C26 O4 124.56(17) y
O3 C26 C22 123.88(17) y
O4 C26 C22 111.54(14) y
O4 C27 C28 110.22(19) y
O4 C27 H27A 109.6 n
C28 C27 H27A 109.6 n
O4 C27 H27B 109.6 n
C28 C27 H27B 109.6 n
H27A C27 H27B 108.1 n
C27 C28 H28A 109.5 n
C27 C28 H28C 109.5 n
H28A C28 H28C 109.5 n
C27 C28 H28B 109.5 n
H28A C28 H28B 109.5 n
H28C C28 H28B 109.5 n
C23 O2 C24 117.83(15) y
C26 O4 C27 117.75(16) y
C1 S1 C15 102.72(8) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.358(2) y
C1 C22 1.511(2) y
C1 S1 1.7708(16) y
C2 C3 1.488(2) y
C2 C14 1.492(2) y
C3 C4 1.395(2) y
C3 C8 1.410(2) y
C4 C5 1.388(3) y
C4 H4 0.9500 n
C5 C6 1.374(3) y
C5 H5 0.9500 n
C6 F1 1.368(2) y
C6 C7 1.375(3) y
C7 C8 1.389(2) y
C7 H7 0.9500 n
C8 C9 1.461(2) y
C9 C10 1.391(2) y
C9 C14 1.405(2) y
C10 C11 1.369(3) y
C10 H10 0.9500 n
C11 F2 1.3696(19) y
C11 C12 1.379(3) y
C12 C13 1.395(2) y
C12 H12 0.9500 n
C13 C14 1.395(2) y
C13 H13 0.94(2) y
C15 C16 1.387(2) y
C15 C20 1.389(2) y
C15 S1 1.7808(18) y
C16 C17 1.387(3) y
C16 H16 0.9500 n
C17 C18 1.386(3) y
C17 H17 0.9500 n
C18 C19 1.391(3) y
C18 C21 1.511(3) y
C19 C20 1.383(3) y
C19 H19 0.9500 n
C20 H20 0.9500 n
C21 H21C 0.9800 n
C21 H21B 0.9800 n
C21 H21A 0.9800 n
C22 C23 1.523(2) y
C22 C26 1.526(2) y
C22 H22 0.944(18) y
C23 O1 1.198(2) y
C23 O2 1.335(2) y
C24 O2 1.456(2) y
C24 C25 1.479(4) y
C24 H24B 0.9900 n
C24 H24A 0.9900 n
C25 H25A 0.9800 n
C25 H25B 0.9800 n
C25 H25C 0.9800 n
C26 O3 1.187(2) y
C26 O4 1.325(2) y
C27 O4 1.463(2) y
C27 C28 1.488(4) y
C27 H27A 0.9900 n
C27 H27B 0.9900 n
C28 H28A 0.9800 n
C28 H28C 0.9800 n
C28 H28B 0.9800 n
