#------------------------------------------------------------------------------
#$Date: 2025-01-07 11:49:03 +0200 (Tue, 07 Jan 2025) $
#$Revision: 297167 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/47/7204776.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_7204776
loop_
_publ_author_name
'Smith, Caroline E.'
'Smith, Philip S.'
'Thomas, Rhodri Ll.'
'Robins, Edward G.'
'Collings, Jonathan C.'
'Dai, Chaoyang'
'Scott, Andrew J.'
'Borwick, Simon'
'Batsanov, Andrei S.'
'Watt, Stephen W.'
'Clark, Stewart J.'
'Viney, Christopher'
'Howard, Judith A. K.'
'Clegg, William'
'Marder, Todd B.'
_publ_section_title
;
 Arene-perfluoroarene interactions in crystal engineering: structural
 preferences in polyfluorinated tolans
;
_journal_coden_ASTM              JMACEP
_journal_issue                   3
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              413
_journal_page_last               420
_journal_paper_doi               10.1039/b314094f
_journal_volume                  14
_journal_year                    2004
_chemical_formula_moiety         'C21 H12 F4 O'
_chemical_formula_sum            'C21 H12 F4 O'
_chemical_formula_weight         356.31
_chemical_melting_point          358.9(8)
_chemical_name_systematic
;
1-(4-tolyloxytetrafluorophenyl)-2-phenylacetylene
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 94.32(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.918(2)
_cell_length_b                   5.777(2)
_cell_length_c                   35.872(9)
_cell_measurement_reflns_used    964
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.24
_cell_volume                     1636.2(8)
_computing_cell_refinement       'SMART-NT V5.0 (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker)'
_computing_data_reduction        'SMART-NT V5.0 (Bruker, 1998)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.913
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       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  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            11617
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0399
_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)+(0.0311P)²+1.0639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                2962
_reflns_number_total             3421
_reflns_threshold_expression     I>2σ(I)
_cod_duplicate_entry             7204775
_cod_data_source_file            b314094f.txt
_cod_data_source_block           4i
_cod_depositor_comments
;
The following automatic conversions were performed:
'_chemical_melting_point' value '85.0--86.5\% C' changed to '358.9(8)'
- converted between degrees Celsius(C) and Kelvins(K), took average
value and fixed precision.

Automatic conversion script
Id: cif_fix_values 1495 2010-12-04 20:58:02Z adriana 

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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7204776
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.47009(15) 0.2958(2) 0.17127(3) 0.0316(3) Uani 1 1 d . . .
C1 C 0.4158(2) 0.2185(3) 0.13614(4) 0.0263(3) Uani 1 1 d . . .
F2 F 0.57217(13) -0.12887(18) 0.14441(3) 0.0352(2) Uani 1 1 d . . .
C2 C 0.4739(2) 0.0109(3) 0.12208(4) 0.0262(3) Uani 1 1 d . . .
F3 F 0.49088(13) -0.25300(17) 0.07299(3) 0.0328(2) Uani 1 1 d . . .
C3 C 0.4316(2) -0.0510(3) 0.08549(4) 0.0253(3) Uani 1 1 d . . .
C4 C 0.3302(2) 0.0877(3) 0.06124(4) 0.0250(3) Uani 1 1 d . . .
F5 F 0.17455(13) 0.43657(18) 0.05393(3) 0.0362(3) Uani 1 1 d . . .
C5 C 0.2726(2) 0.2953(3) 0.07581(4) 0.0263(3) Uani 1 1 d . . .
F6 F 0.25455(13) 0.55770(17) 0.12573(3) 0.0356(2) Uani 1 1 d . . .
C6 C 0.3137(2) 0.3573(3) 0.11253(4) 0.0263(3) Uani 1 1 d . . .
C7 C 0.2837(2) 0.0210(3) 0.02345(4) 0.0283(3) Uani 1 1 d . . .
C8 C 0.2414(2) -0.0320(3) -0.00814(4) 0.0285(4) Uani 1 1 d . . .
C9 C 0.1911(2) -0.0875(3) -0.04650(4) 0.0259(3) Uani 1 1 d . . .
C10 C 0.2393(2) -0.2968(3) -0.06214(5) 0.0292(4) Uani 1 1 d . . .
H10 H 0.303(3) -0.409(4) -0.0475(5) 0.036(5) Uiso 1 1 d . . .
C11 C 0.1927(2) -0.3445(3) -0.09952(5) 0.0314(4) Uani 1 1 d . . .
H11 H 0.225(2) -0.495(4) -0.1105(5) 0.037(5) Uiso 1 1 d . . .
C12 C 0.0978(2) -0.1854(3) -0.12124(5) 0.0309(4) Uani 1 1 d . . .
H12 H 0.066(2) -0.218(4) -0.1482(6) 0.038(5) Uiso 1 1 d . . .
C13 C 0.0490(2) 0.0228(3) -0.10567(5) 0.0311(4) Uani 1 1 d . . .
H13 H -0.014(3) 0.132(4) -0.1209(5) 0.036(5) Uiso 1 1 d . . .
C14 C 0.0952(2) 0.0724(3) -0.06848(5) 0.0285(4) Uani 1 1 d . . .
H14 H 0.063(2) 0.212(4) -0.0575(5) 0.031(5) Uiso 1 1 d . . .
C15 C 0.36774(19) 0.2501(3) 0.20081(4) 0.0238(3) Uani 1 1 d . . .
C16 C 0.3736(2) 0.4132(3) 0.22903(4) 0.0249(3) Uani 1 1 d . . .
H16 H 0.435(2) 0.550(3) 0.2261(5) 0.028(5) Uiso 1 1 d . . .
C17 C 0.2896(2) 0.3695(3) 0.26106(4) 0.0263(3) Uani 1 1 d . . .
H17 H 0.297(2) 0.480(4) 0.2816(5) 0.036(5) Uiso 1 1 d . . .
C18 C 0.20071(19) 0.1639(3) 0.26503(4) 0.0259(3) Uani 1 1 d . . .
C19 C 0.1928(2) 0.0067(3) 0.23542(5) 0.0277(3) Uani 1 1 d . . .
H19 H 0.131(2) -0.137(4) 0.2371(5) 0.031(5) Uiso 1 1 d . . .
C20 C 0.2759(2) 0.0469(3) 0.20318(4) 0.0270(3) Uani 1 1 d . . .
H20 H 0.274(2) -0.062(3) 0.1841(5) 0.031(5) Uiso 1 1 d . . .
C21 C 0.1232(2) 0.1053(4) 0.30104(5) 0.0347(4) Uani 1 1 d . . .
H21C H 0.095(3) 0.249(4) 0.3148(7) 0.057(7) Uiso 1 1 d . . .
H21B H 0.019(3) 0.012(4) 0.2959(6) 0.043(6) Uiso 1 1 d . . .
H21A H 0.201(3) 0.019(4) 0.3171(6) 0.040(5) 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O C15 118.13(12) . . ?
O C1 C6 120.06(15) . . ?
O C1 C2 121.53(15) . . ?
C6 C1 C2 118.14(14) . . ?
F2 C2 C3 120.07(15) . . ?
F2 C2 C1 119.58(14) . . ?
C3 C2 C1 120.35(15) . . ?
F3 C3 C2 118.43(14) . . ?
F3 C3 C4 119.32(14) . . ?
C2 C3 C4 122.25(15) . . ?
C3 C4 C5 116.69(14) . . ?
C3 C4 C7 122.13(15) . . ?
C5 C4 C7 121.17(15) . . ?
F5 C5 C6 119.08(15) . . ?
F5 C5 C4 119.64(14) . . ?
C6 C5 C4 121.28(15) . . ?
F6 C6 C5 119.66(15) . . ?
F6 C6 C1 119.06(14) . . ?
C5 C6 C1 121.28(15) . . ?
C8 C7 C4 178.48(18) . . ?
C7 C8 C9 177.99(18) . . ?
C10 C9 C14 119.84(15) . . ?
C10 C9 C8 120.75(15) . . ?
C14 C9 C8 119.39(15) . . ?
C11 C10 C9 119.80(16) . . ?
C12 C11 C10 120.19(16) . . ?
C11 C12 C13 120.08(15) . . ?
C14 C13 C12 120.23(17) . . ?
C13 C14 C9 119.85(16) . . ?
C16 C15 C20 121.42(14) . . ?
C16 C15 O 115.74(14) . . ?
C20 C15 O 122.67(14) . . ?
C15 C16 C17 119.27(15) . . ?
C18 C17 C16 120.99(15) . . ?
C17 C18 C19 118.12(14) . . ?
C17 C18 C21 121.30(15) . . ?
C19 C18 C21 120.49(16) . . ?
C20 C19 C18 121.76(15) . . ?
C15 C20 C19 118.37(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O C1 1.3752(19) . ?
O C15 1.4064(18) . ?
C1 C6 1.383(2) . ?
C1 C2 1.393(2) . ?
F2 C2 1.3434(18) . ?
C2 C3 1.377(2) . ?
F3 C3 1.3474(18) . ?
C3 C4 1.392(2) . ?
C4 C5 1.398(2) . ?
C4 C7 1.431(2) . ?
F5 C5 1.3389(18) . ?
C5 C6 1.380(2) . ?
F6 C6 1.3481(18) . ?
C7 C8 1.197(2) . ?
C8 C9 1.440(2) . ?
C9 C10 1.399(2) . ?
C9 C14 1.400(2) . ?
C10 C11 1.391(2) . ?
C11 C12 1.389(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.386(2) . ?
C15 C16 1.381(2) . ?
C15 C20 1.387(2) . ?
C16 C17 1.393(2) . ?
C17 C18 1.393(2) . ?
C18 C19 1.395(2) . ?
C18 C21 1.510(2) . ?
C19 C20 1.393(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4415028
