#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:38:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178475 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/96/4029634.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_4029634
loop_
_publ_author_name
'Widner, Danielle L.'
'Knauf, Qianwei R.'
'Merucci, Mark T.'
'Fritz, Thomas R.'
'Sauer, Jon S.'
'Speetzen, Erin D.'
'Bosch, Eric'
'Bowling, Nathan P.'
_publ_section_title
;
 Intramolecular halogen bonding supported by an aryldiyne linker.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6269
_journal_page_last               6278
_journal_paper_doi               10.1021/jo501015x
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C25 H14 Cl F3 O2'
_chemical_formula_weight         438.81
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                102.2720(10)
_cell_angle_beta                 101.0770(10)
_cell_angle_gamma                102.5290(10)
_cell_formula_units_Z            2
_cell_length_a                   7.4366(4)
_cell_length_b                   10.2527(5)
_cell_length_c                   13.9827(7)
_cell_measurement_reflns_used    4878
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.90
_cell_volume                     984.72(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'XSeed (Barbour, 2003)'
_computing_publication_material  'XSeed (Barbour, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      99(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12836
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.141
_diffrn_reflns_theta_min         1.539
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7045
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       cut
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0386P)²+0.3760P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3666
_reflns_number_total             4365
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo501015x_si_001.cif
_cod_data_source_block           16
_cod_depositor_comments
'Adding full bibliography for 4029631--4029636.cif.'
_cod_database_code               4029634
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.830
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl1 Cl 0.32577(5) 0.32094(4) 0.04080(3) 0.02093(10) Uani 1 1 d . .
F1 F 0.46716(13) 0.12830(9) -0.41732(6) 0.0276(2) Uani 1 1 d . .
O1 O 0.31964(16) 0.44024(11) 0.25248(8) 0.0256(2) Uani 1 1 d . .
C1 C 0.33531(19) 0.24124(14) -0.07973(10) 0.0164(3) Uani 1 1 d . .
F2 F 0.18329(13) 0.00296(10) -0.43927(7) 0.0317(2) Uani 1 1 d . .
O2 O 0.18166(15) 0.50452(10) 0.69398(7) 0.0225(2) Uani 1 1 d . .
C2 C 0.3765(2) 0.32121(14) -0.14502(11) 0.0187(3) Uani 1 1 d . .
H2 H 0.3962 0.4187 -0.1242 0.022 Uiso 1 1 calc R U
F3 F 0.42300(14) -0.06758(9) -0.38036(7) 0.0291(2) Uani 1 1 d . .
C3 C 0.3890(2) 0.25868(14) -0.24075(10) 0.0179(3) Uani 1 1 d . .
H3 H 0.4195 0.3133 -0.2854 0.021 Uiso 1 1 calc R U
C4 C 0.35658(19) 0.11563(14) -0.27103(10) 0.0161(3) Uani 1 1 d . .
C5 C 0.31489(19) 0.03527(14) -0.20548(10) 0.0169(3) Uani 1 1 d . .
H5 H 0.2937 -0.0623 -0.2271 0.020 Uiso 1 1 calc R U
C6 C 0.30377(19) 0.09645(14) -0.10829(10) 0.0159(3) Uani 1 1 d . .
C7 C 0.26249(19) 0.01515(14) -0.03993(10) 0.0172(3) Uani 1 1 d . .
C8 C 0.22752(19) -0.04977(14) 0.01915(10) 0.0167(3) Uani 1 1 d . .
C9 C 0.18824(19) -0.12838(14) 0.08958(10) 0.0156(3) Uani 1 1 d . .
C10 C 0.1662(2) -0.27129(15) 0.06449(11) 0.0191(3) Uani 1 1 d . .
H10 H 0.1758 -0.3166 -0.0003 0.023 Uiso 1 1 calc R U
C11 C 0.1307(2) -0.34778(15) 0.13240(11) 0.0212(3) Uani 1 1 d . .
H11 H 0.1175 -0.4447 0.1142 0.025 Uiso 1 1 calc R U
C12 C 0.1142(2) -0.28361(15) 0.22714(11) 0.0210(3) Uani 1 1 d . .
H12 H 0.0886 -0.3366 0.2734 0.025 Uiso 1 1 calc R U
C13 C 0.13516(19) -0.14220(15) 0.25392(11) 0.0189(3) Uani 1 1 d . .
H13 H 0.1238 -0.0986 0.3188 0.023 Uiso 1 1 calc R U
C14 C 0.17297(19) -0.06250(14) 0.18645(10) 0.0154(3) Uani 1 1 d . .
C15 C 0.20005(19) 0.08432(15) 0.21835(10) 0.0171(3) Uani 1 1 d . .
C16 C 0.2250(2) 0.20659(15) 0.25098(10) 0.0184(3) Uani 1 1 d . .
C17 C 0.2642(2) 0.35482(14) 0.29721(10) 0.0177(3) Uani 1 1 d . .
C18 C 0.23782(19) 0.39479(14) 0.40049(10) 0.0157(3) Uani 1 1 d . .
C19 C 0.16670(19) 0.29600(14) 0.44898(10) 0.0173(3) Uani 1 1 d . .
H19 H 0.1314 0.2003 0.4145 0.021 Uiso 1 1 calc R U
C20 C 0.1474(2) 0.33609(14) 0.54588(11) 0.0188(3) Uani 1 1 d . .
H20 H 0.0965 0.2683 0.5775 0.023 Uiso 1 1 calc R U
C21 C 0.20254(19) 0.47623(15) 0.59793(10) 0.0173(3) Uani 1 1 d . .
C22 C 0.2733(2) 0.57648(14) 0.55077(10) 0.0175(3) Uani 1 1 d . .
H22 H 0.3098 0.6721 0.5857 0.021 Uiso 1 1 calc R U
C23 C 0.28960(19) 0.53501(14) 0.45285(11) 0.0177(3) Uani 1 1 d . .
H23 H 0.3368 0.6030 0.4205 0.021 Uiso 1 1 calc R U
C24 C 0.3592(2) 0.04586(15) -0.37610(11) 0.0199(3) Uani 1 1 d . .
C25 C 0.2350(2) 0.64626(15) 0.75116(11) 0.0241(3) Uani 1 1 d . .
H25A H 0.3706 0.6867 0.7586 0.036 Uiso 1 1 calc R U
H25B H 0.2107 0.6516 0.8181 0.036 Uiso 1 1 calc R U
H25C H 0.1603 0.6976 0.7160 0.036 Uiso 1 1 calc R U
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 121.59(13)
C2 C1 Cl1 119.46(11)
C6 C1 Cl1 118.94(10)
C21 O2 C25 118.10(11)
C1 C2 C3 119.86(13)
C2 C3 C4 119.60(13)
C3 C4 C5 120.53(13)
C3 C4 C24 120.20(12)
C5 C4 C24 119.24(12)
C4 C5 C6 120.75(13)
C5 C6 C1 117.66(12)
C5 C6 C7 121.30(12)
C1 C6 C7 121.04(12)
C8 C7 C6 178.19(15)
C7 C8 C9 179.06(15)
C10 C9 C14 118.72(12)
C10 C9 C8 120.64(13)
C14 C9 C8 120.64(12)
C11 C10 C9 121.09(13)
C10 C11 C12 120.31(13)
C13 C12 C11 119.81(13)
C12 C13 C14 120.77(13)
C13 C14 C9 119.30(12)
C13 C14 C15 119.02(12)
C9 C14 C15 121.65(12)
C16 C15 C14 176.02(15)
C15 C16 C17 175.93(15)
O1 C17 C16 120.98(13)
O1 C17 C18 122.62(13)
C16 C17 C18 116.38(12)
C23 C18 C19 118.64(13)
C23 C18 C17 119.37(12)
C19 C18 C17 121.96(12)
C20 C19 C18 120.69(13)
C19 C20 C21 120.10(13)
O2 C21 C20 115.42(12)
O2 C21 C22 124.50(13)
C20 C21 C22 120.08(13)
C23 C22 C21 119.27(13)
C22 C23 C18 121.19(13)
F1 C24 F3 106.94(12)
F1 C24 F2 106.10(11)
F3 C24 F2 105.99(12)
F1 C24 C4 113.10(12)
F3 C24 C4 112.50(11)
F2 C24 C4 111.70(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7317(14)
F1 C24 1.3348(16)
O1 C17 1.2262(17)
C1 C2 1.3843(19)
C1 C6 1.4068(19)
F2 C24 1.3513(17)
O2 C21 1.3588(16)
O2 C25 1.4292(17)
C2 C3 1.386(2)
F3 C24 1.3425(16)
C3 C4 1.3899(19)
C4 C5 1.3909(19)
C4 C24 1.4969(19)
C5 C6 1.3966(19)
C6 C7 1.4294(19)
C7 C8 1.198(2)
C8 C9 1.4320(19)
C9 C10 1.3971(19)
C9 C14 1.4168(19)
C10 C11 1.382(2)
C11 C12 1.389(2)
C12 C13 1.384(2)
C13 C14 1.4023(19)
C14 C15 1.4332(19)
C15 C16 1.199(2)
C16 C17 1.4595(19)
C17 C18 1.4778(19)
C18 C23 1.3984(19)
C18 C19 1.4009(19)
C19 C20 1.3743(19)
C20 C21 1.396(2)
C21 C22 1.3981(19)
C22 C23 1.3815(19)
