#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/97/7019701.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_7019701
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         'C21 H16 F2 O4'
_chemical_formula_sum            'C21 H16 F2 O4'
_chemical_formula_weight         370.34
_chemical_name_systematic
;
1,1-di(ethoxycarbonyl)-2-(9H-3,6-difluoro-fluoren-9-ylidene)-ethene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                HOS-HG-120-02
_audit_creation_date             2012-01-18
_cell_angle_alpha                90.00
_cell_angle_beta                 101.410(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.5285(2)
_cell_length_b                   45.944(2)
_cell_length_c                   8.2961(4)
_cell_measurement_reflns_used    4296
_cell_measurement_temperature    100
_cell_measurement_theta_max      55.1395
_cell_measurement_theta_min      3.8485
_cell_volume                     1691.95(13)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'PROTEUM2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'focusing multilayer optic'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18616
_diffrn_reflns_theta_full        54.79
_diffrn_reflns_theta_max         54.79
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.972
_exptl_absorpt_correction_T_max  0.96683
_exptl_absorpt_correction_T_min  0.83181
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0544
_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)+(0.0518P)²+2.6833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1465
_reflns_number_gt                1705
_reflns_number_total             2071
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt30195d.txt
_cod_data_source_block           6979_8
_cod_original_cell_volume        1691.96(14)
_cod_original_sg_symbol_Hall     '-p 2yn'
_cod_original_sg_symbol_H-M      'p 21/n'
_cod_database_code               7019701
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
F1 F 1.0261(4) 0.29162(4) 0.5844(2) 0.0326(6) Uani 1 1 d .
F2 F -0.3682(5) 0.26085(4) -0.1136(2) 0.0358(6) Uani 1 1 d .
O4 O 0.4912(5) 0.40548(5) -0.1658(3) 0.0311(7) Uani 1 1 d .
O3 O 0.4163(7) 0.45208(6) -0.1127(3) 0.0458(8) Uani 1 1 d .
O1 O -0.0933(6) 0.42455(5) 0.2330(3) 0.0330(7) Uani 1 1 d .
O2 O 0.0731(7) 0.46204(5) 0.1052(4) 0.0547(9) Uani 1 1 d .
C15 C 0.2312(7) 0.41511(7) 0.0462(4) 0.0218(8) Uani 1 1 d .
C8 C 0.4360(8) 0.31550(7) 0.2521(4) 0.0229(9) Uani 1 1 d .
C12 C -0.3245(8) 0.31147(8) -0.1348(4) 0.0267(9) Uani 1 1 d .
H12 H -0.4962 0.3115 -0.2217 0.032 Uiso 1 1 calc R
C16 C 0.0531(8) 0.43422(8) 0.1388(5) 0.0261(9) Uani 1 1 d .
C19 C 0.3868(8) 0.42702(8) -0.0832(4) 0.0249(9) Uani 1 1 d .
C11 C -0.2183(8) 0.28583(8) -0.0594(4) 0.0275(9) Uani 1 1 d .
C13 C -0.1771(8) 0.33712(8) -0.0822(4) 0.0263(9) Uani 1 1 d .
H13 H -0.2456 0.3551 -0.1322 0.032 Uiso 1 1 calc R
C1 C 0.2522(7) 0.38745(8) 0.0842(4) 0.0237(9) Uani 1 1 d .
C20 C 0.6500(8) 0.41460(8) -0.2949(4) 0.0313(10) Uani 1 1 d .
H20A H 0.7924 0.3991 -0.3129 0.038 Uiso 1 1 calc R
H20B H 0.7678 0.4324 -0.2595 0.038 Uiso 1 1 calc R
C14 C 0.0720(8) 0.33610(7) 0.0449(4) 0.0237(9) Uani 1 1 d .
C10 C 0.0284(8) 0.28370(8) 0.0677(4) 0.0254(9) Uani 1 1 d .
H10 H 0.0948 0.2655 0.1161 0.030 Uiso 1 1 calc R
C5 C 0.9142(8) 0.33879(7) 0.4778(4) 0.0256(9) Uani 1 1 d .
H5 H 1.0783 0.3462 0.5564 0.031 Uiso 1 1 calc R
C7 C 0.6127(8) 0.29692(8) 0.3633(4) 0.0248(9) Uani 1 1 d .
H7 H 0.5747 0.2766 0.3638 0.030 Uiso 1 1 calc R
C6 C 0.8476(8) 0.30959(8) 0.4736(4) 0.0269(9) Uani 1 1 d .
C9 C 0.1754(8) 0.30971(7) 0.1216(4) 0.0228(9) Uani 1 1 d .
C2 C 0.2728(8) 0.35964(7) 0.1236(4) 0.0233(9) Uani 1 1 d .
C3 C 0.4996(8) 0.34547(7) 0.2545(4) 0.0233(9) Uani 1 1 d .
C21 C 0.4317(9) 0.42048(9) -0.4532(5) 0.0369(10) Uani 1 1 d .
H21B H 0.5424 0.4270 -0.5368 0.055 Uiso 1 1 calc R
H21C H 0.2895 0.4356 -0.4352 0.055 Uiso 1 1 calc R
H21A H 0.3210 0.4026 -0.4906 0.055 Uiso 1 1 calc R
C18 C 0.1316(10) 0.50056(9) 0.3039(5) 0.0494(12) Uani 1 1 d .
H18B H 0.2694 0.5102 0.2436 0.074 Uiso 1 1 calc R
H18A H 0.2466 0.4878 0.3885 0.074 Uiso 1 1 calc R
H18C H 0.0250 0.5153 0.3562 0.074 Uiso 1 1 calc R
C4 C 0.7381(8) 0.35722(8) 0.3656(4) 0.0263(9) Uani 1 1 d .
H4 H 0.7804 0.3775 0.3651 0.032 Uiso 1 1 calc R
C17 C -0.0907(10) 0.48289(9) 0.1878(6) 0.0547(13) Uani 1 1 d .
H17A H -0.2255 0.4724 0.2485 0.066 Uiso 1 1 calc R
H17B H -0.2155 0.4957 0.1056 0.066 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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 0.0200
0.00 1.00 -1.00 0.0200
0.00 1.00 0.00 0.0200
0.00 -1.00 0.00 0.0200
1.00 -1.00 0.00 0.1800
-1.00 1.00 0.00 0.1700
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
C19 O4 C20 115.8(3) y
C16 O2 C17 118.3(3) y
C1 C15 C19 120.3(3) y
C1 C15 C16 117.7(3) y
C19 C15 C16 121.9(3) y
C7 C8 C3 120.2(3) y
C7 C8 C9 131.0(3) y
C3 C8 C9 108.8(3) y
C11 C12 C13 118.9(3) y
C11 C12 H12 120.6 n
C13 C12 H12 120.6 n
O1 C16 O2 124.4(3) y
O1 C16 C15 122.4(3) y
O2 C16 C15 113.1(3) y
O3 C19 O4 122.9(3) y
O3 C19 C15 126.0(3) y
O4 C19 C15 111.1(3) y
F2 C11 C12 117.7(3) y
F2 C11 C10 117.9(3) y
C12 C11 C10 124.5(3) y
C12 C13 C14 118.8(3) y
C12 C13 H13 120.6 n
C14 C13 H13 120.6 n
C15 C1 C2 179.6(4) y
O4 C20 C21 110.9(3) y
O4 C20 H20A 109.5 n
C21 C20 H20A 109.5 n
O4 C20 H20B 109.5 n
C21 C20 H20B 109.5 n
H20A C20 H20B 108.0 n
C13 C14 C9 121.5(3) y
C13 C14 C2 130.5(3) y
C9 C14 C2 108.1(3) y
C11 C10 C9 116.5(3) y
C11 C10 H10 121.7 n
C9 C10 H10 121.7 n
C6 C5 C4 119.0(3) y
C6 C5 H5 120.5 n
C4 C5 H5 120.5 n
C6 C7 C8 116.5(3) y
C6 C7 H7 121.7 n
C8 C7 H7 121.7 n
F1 C6 C5 118.2(3) y
F1 C6 C7 117.6(3) y
C5 C6 C7 124.2(3) y
C10 C9 C14 119.8(3) y
C10 C9 C8 131.1(3) y
C14 C9 C8 109.1(3) y
C1 C2 C14 126.3(3) y
C1 C2 C3 127.6(3) y
C14 C2 C3 106.1(3) y
C4 C3 C8 121.5(3) y
C4 C3 C2 130.6(3) y
C8 C3 C2 107.9(3) y
C20 C21 H21B 109.5 n
C20 C21 H21C 109.5 n
H21B C21 H21C 109.5 n
C20 C21 H21A 109.5 n
H21B C21 H21A 109.5 n
H21C C21 H21A 109.5 n
C17 C18 H18B 109.5 n
C17 C18 H18A 109.5 n
H18B C18 H18A 109.5 n
C17 C18 H18C 109.5 n
H18B C18 H18C 109.5 n
H18A C18 H18C 109.5 n
C3 C4 C5 118.6(3) y
C3 C4 H4 120.7 n
C5 C4 H4 120.7 n
O2 C17 C18 108.7(4) y
O2 C17 H17A 110.0 n
C18 C17 H17A 110.0 n
O2 C17 H17B 110.0 n
C18 C17 H17B 110.0 n
H17A C17 H17B 108.3 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C6 1.373(4) y
F2 C11 1.364(4) y
O4 C19 1.342(4) y
O4 C20 1.465(4) y
O3 C19 1.190(4) y
O1 C16 1.205(4) y
O2 C16 1.315(4) y
O2 C17 1.462(5) y
C15 C1 1.308(5) y
C15 C19 1.499(5) y
C15 C16 1.502(5) y
C8 C7 1.389(5) y
C8 C3 1.406(5) y
C8 C9 1.459(5) y
C12 C11 1.375(5) y
C12 C13 1.382(5) y
C12 H12 0.9500 n
C11 C10 1.380(5) y
C13 C14 1.384(5) y
C13 H13 0.9500 n
C1 C2 1.318(5) y
C20 C21 1.503(5) y
C20 H20A 0.9900 n
C20 H20B 0.9900 n
C14 C9 1.406(5) y
C14 C2 1.479(5) y
C10 C9 1.398(5) y
C10 H10 0.9500 n
C5 C6 1.374(5) y
C5 C4 1.388(5) y
C5 H5 0.9500 n
C7 C6 1.386(5) y
C7 H7 0.9500 n
C2 C3 1.489(5) y
C3 C4 1.383(5) y
C21 H21B 0.9800 n
C21 H21C 0.9800 n
C21 H21A 0.9800 n
C18 C17 1.489(6) y
C18 H18B 0.9800 n
C18 H18A 0.9800 n
C18 H18C 0.9800 n
C4 H4 0.9500 n
C17 H17A 0.9900 n
C17 H17B 0.9900 n
