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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/39/4503931.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_4503931
loop_
_publ_author_name
'Choudhury, Angshuman R.'
'Bhat, Ramakrishna G.'
'Guru Row, Tayur N.'
'Chandrasekaran, Srinivasan'
_publ_section_title
;
 Weak Csp3−H···F−C Interaction
 Overshadows the Strong C⋮C−H···OC
 Hydrogen Bond:  Structure of Pentafluorophenyl Prop-2-ynyl
 Carbonate
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              844
_journal_paper_doi               10.1021/cg060489t
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C10 H3 F5 O3'
_chemical_formula_weight         266.12
_space_group_IT_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.305(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3166(11)
_cell_length_b                   17.769(3)
_cell_length_c                   7.4574(12)
_cell_measurement_temperature    90(2)
_cell_volume                     959.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0134
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6981
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.9433
_exptl_absorpt_correction_T_min  0.9080
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0433P)²+0.2846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0739
_reflns_number_gt                1616
_reflns_number_total             1753
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060489tsi20060725_070918.cif
_cod_data_source_block           rgb90k_m
_cod_original_cell_volume        959.3(3)
_cod_database_code               4503931
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
F2 F 0.13598(11) 0.61003(4) -0.40554(10) 0.0240(2) Uani 1 1 d
F5 F 0.33253(10) 0.71998(4) 0.27458(10) 0.0227(2) Uani 1 1 d
F1 F -0.11623(10) 0.61510(4) -0.17178(10) 0.0222(2) Uani 1 1 d
F4 F 0.57946(10) 0.72010(4) 0.03605(11) 0.0234(2) Uani 1 1 d
F3 F 0.48126(10) 0.66448(4) -0.30339(10) 0.0228(2) Uani 1 1 d
O1 O -0.02222(12) 0.67431(5) 0.17552(12) 0.0181(2) Uani 1 1 d
O3 O -0.20924(12) 0.62941(5) 0.34457(12) 0.0180(2) Uani 1 1 d
O2 O -0.05362(12) 0.54698(5) 0.19003(12) 0.0211(2) Uani 1 1 d
C8 C -0.29959(18) 0.56691(7) 0.42306(17) 0.0183(3) Uani 1 1 d
C2 C 0.05627(16) 0.63924(7) -0.11818(17) 0.0172(3) Uani 1 1 d
C3 C 0.18324(18) 0.63731(7) -0.23771(17) 0.0177(3) Uani 1 1 d
C4 C 0.35935(17) 0.66542(7) -0.18648(17) 0.0173(3) Uani 1 1 d
C1 C 0.10423(17) 0.66738(6) 0.05537(17) 0.0159(3) Uani 1 1 d
C5 C 0.40809(16) 0.69391(7) -0.01445(17) 0.0172(3) Uani 1 1 d
C6 C 0.28187(17) 0.69425(7) 0.10636(17) 0.0166(3) Uani 1 1 d
C7 C -0.09263(16) 0.60884(7) 0.23320(16) 0.0162(3) Uani 1 1 d
C10 C -0.58543(19) 0.51815(7) 0.19419(19) 0.0228(3) Uani 1 1 d
C9 C -0.45640(17) 0.53900(7) 0.29632(17) 0.0190(3) Uani 1 1 d
H1 H -0.342(2) 0.5886(8) 0.529(2) 0.021(4) Uiso 1 1 d
H2 H -0.213(2) 0.5285(8) 0.4572(19) 0.016(3) Uiso 1 1 d
H3 H -0.684(3) 0.5027(10) 0.114(3) 0.035(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
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
C7 O1 C1 116.48(9)
C7 O3 C8 114.33(9)
O3 C8 C9 110.94(10)
O3 C8 H1 104.0(9)
C9 C8 H1 110.2(9)
O3 C8 H2 109.6(8)
C9 C8 H2 111.3(9)
H1 C8 H2 110.6(12)
F1 C2 C3 119.59(11)
F1 C2 C1 119.72(11)
C3 C2 C1 120.68(11)
F2 C3 C2 120.41(11)
F2 C3 C4 119.53(11)
C2 C3 C4 120.04(12)
F3 C4 C5 120.37(11)
F3 C4 C3 119.92(11)
C5 C4 C3 119.70(11)
O1 C1 C2 122.33(11)
O1 C1 C6 118.70(11)
C2 C1 C6 118.82(11)
F4 C5 C4 119.70(11)
F4 C5 C6 120.16(11)
C4 C5 C6 120.13(11)
F5 C6 C5 119.56(11)
F5 C6 C1 119.84(11)
C5 C6 C1 120.60(12)
O2 C7 O3 128.66(11)
O2 C7 O1 125.75(11)
O3 C7 O1 105.58(10)
C9 C10 H3 179.0(12)
C10 C9 C8 178.32(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F2 C3 1.3401(15)
F5 C6 1.3364(15)
F1 C2 1.3383(14)
F4 C5 1.3394(14)
F3 C4 1.3344(14)
O1 C7 1.3666(15)
O1 C1 1.3833(15)
O3 C7 1.3251(15)
O3 C8 1.4577(15)
O2 C7 1.1916(15)
C8 C9 1.4636(18)
C8 H1 0.968(15)
C8 H2 0.940(15)
C2 C3 1.3777(18)
C2 C1 1.3845(18)
C3 C4 1.3833(18)
C4 C5 1.3773(18)
C1 C6 1.3853(17)
C5 C6 1.3802(18)
C10 C9 1.184(2)
C10 H3 0.913(19)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 O3 C8 C9 -81.23(13)
F1 C2 C3 F2 -1.37(17)
C1 C2 C3 F2 -179.98(11)
F1 C2 C3 C4 176.94(10)
C1 C2 C3 C4 -1.67(18)
F2 C3 C4 F3 -0.71(17)
C2 C3 C4 F3 -179.03(11)
F2 C3 C4 C5 179.62(11)
C2 C3 C4 C5 1.29(18)
C7 O1 C1 C2 65.98(15)
C7 O1 C1 C6 -118.47(12)
F1 C2 C1 O1 -2.47(17)
C3 C2 C1 O1 176.13(11)
F1 C2 C1 C6 -178.01(10)
C3 C2 C1 C6 0.59(18)
F3 C4 C5 F4 -0.67(17)
C3 C4 C5 F4 179.01(10)
F3 C4 C5 C6 -179.53(11)
C3 C4 C5 C6 0.14(18)
F4 C5 C6 F5 -0.84(17)
C4 C5 C6 F5 178.02(10)
F4 C5 C6 C1 179.92(10)
C4 C5 C6 C1 -1.22(18)
O1 C1 C6 F5 5.91(17)
C2 C1 C6 F5 -178.38(10)
O1 C1 C6 C5 -174.85(10)
C2 C1 C6 C5 0.85(18)
C8 O3 C7 O2 0.14(18)
C8 O3 C7 O1 -179.60(9)
C1 O1 C7 O2 0.55(18)
C1 O1 C7 O3 -179.70(9)
O3 C8 C9 C10 -66(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9645932
2 PubChem 11471102
