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#$Date: 2016-05-31 10:54:22 +0300 (Tue, 31 May 2016) $
#$Revision: 183168 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/89/7118963.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_7118963
loop_
_publ_author_name
'Dhananjay Dey'
'Subhrajyoti Bhandary'
'Abhishek Sirohiwal'
'Venkatesha R. Hathwar'
'Deepak Chopra'
_publ_section_title
;
 'Conformational lock' via unusual intramolecular C-F^...^O[double bond,
 length as m-dash]C and C-H^...^Cl-C parallel dipoles observed in in situ
 cryocrystallized liquids
;
_journal_name_full               Chem.Commun.
_journal_page_first              7225
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C7 H3 Cl F2 O'
_chemical_formula_weight         176.54
_chemical_melting_point          278.2
_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-2014/7
_audit_update_record
;
2016-04-14 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                100.231(3)
_cell_angle_beta                 95.404(3)
_cell_angle_gamma                91.365(3)
_cell_formula_units_Z            4
_cell_length_a                   7.4814(4)
_cell_length_b                   8.5648(4)
_cell_length_c                   10.7372(6)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.42
_cell_volume                     673.48(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'WINGX (Farrugia, 2014) and PLATON'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2014 (Burla et al., 2014)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.758
_diffrn_measured_fraction_theta_max 0.711
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 0.758
_diffrn_reflns_Laue_measured_fraction_max 0.711
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16476
_diffrn_reflns_point_group_measured_fraction_full 0.758
_diffrn_reflns_point_group_measured_fraction_max 0.711
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_min         1.937
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.7107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0345
_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)+(0.0429P)²+0.6610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2093
_reflns_number_total             2284
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc02535h2.cif
_cod_data_source_block           25dfbc
_cod_database_code               7118963
_shelx_shelxl_version_number     2014/7
_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   0.857
_shelx_estimated_absorpt_t_max   0.857
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.13142(11) 0.43677(7) 0.86101(5) 0.0391(2) Uani 1 1 d . . . . .
F1 F 0.8418(2) 0.59832(14) 0.51842(11) 0.0286(4) Uani 1 1 d . . . . .
F2 F 1.1349(2) 1.04263(16) 0.91128(12) 0.0390(4) Uani 1 1 d . . . . .
O1 O 0.8860(3) 0.38599(18) 0.67245(15) 0.0375(5) Uani 1 1 d . . . . .
C2 C 0.9152(3) 0.7069(2) 0.61788(18) 0.0214(6) Uani 1 1 d . . . . .
C5 C 1.0607(4) 0.9307(2) 0.81345(19) 0.0268(6) Uani 1 1 d . . . . .
C1 C 0.9882(3) 0.6576(2) 0.72796(17) 0.0205(6) Uani 1 1 d . . . . .
C3 C 0.9144(3) 0.8635(2) 0.60429(18) 0.0230(6) Uani 1 1 d . . . . .
H3 H 0.8648 0.8921 0.5271 0.028 Uiso 1 1 calc R U . . .
C7 C 0.9811(4) 0.4872(3) 0.73772(19) 0.0269(6) Uani 1 1 d . . . . .
C6 C 1.0639(3) 0.7746(2) 0.82812(18) 0.0238(6) Uani 1 1 d . . . . .
H6 H 1.1166 0.7467 0.9047 0.029 Uiso 1 1 calc R U . . .
C4 C 0.9869(4) 0.9791(2) 0.7046(2) 0.0256(6) Uani 1 1 d . . . . .
H4 H 0.9858 1.0884 0.6986 0.031 Uiso 1 1 calc R U . . .
Cl1A Cl 0.37814(11) -0.23623(6) 0.12984(5) 0.0415(2) Uani 1 1 d . . . . .
F2A F 0.3520(2) 0.35171(16) 0.09780(13) 0.0373(4) Uani 1 1 d . . . . .
F1A F 0.6650(2) 0.08549(15) 0.47966(11) 0.0284(4) Uani 1 1 d . . . . .
O1A O 0.6022(3) -0.19547(19) 0.32995(15) 0.0382(5) Uani 1 1 d . . . . .
C1A C 0.5096(3) 0.0495(2) 0.27254(18) 0.0204(6) Uani 1 1 d . . . . .
C5A C 0.4323(4) 0.2843(3) 0.1918(2) 0.0253(6) Uani 1 1 d . . . . .
C4A C 0.5108(4) 0.3816(2) 0.3005(2) 0.0266(6) Uani 1 1 d . . . . .
H4A H 0.5118 0.4939 0.3083 0.032 Uiso 1 1 calc R U . . .
C2A C 0.5871(3) 0.1487(2) 0.38281(18) 0.0219(6) Uani 1 1 d . . . . .
C7A C 0.5170(4) -0.1252(2) 0.26164(18) 0.0270(6) Uani 1 1 d . . . . .
C3A C 0.5881(4) 0.3113(2) 0.3979(2) 0.0262(6) Uani 1 1 d . . . . .
H3A H 0.6415 0.3750 0.4745 0.031 Uiso 1 1 calc R U . . .
C6A C 0.4295(3) 0.1216(2) 0.17504(18) 0.0232(6) Uani 1 1 d . . . . .
H6A H 0.3742 0.0588 0.0986 0.028 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
F1 C2 C3 117.23(18) . .
F1 C2 C1 119.75(17) . .
C3 C2 C1 123.02(18) . .
F2 C5 C6 117.96(19) . .
F2 C5 C4 118.50(18) . .
C6 C5 C4 123.54(19) . .
C2 C1 C6 117.58(18) . .
C2 C1 C7 120.39(18) . .
C6 C1 C7 122.02(18) . .
C2 C3 C4 119.13(19) . .
C2 C3 H3 120.4 . .
C4 C3 H3 120.4 . .
O1 C7 C1 126.3(2) . .
O1 C7 Cl1 119.12(17) . .
C1 C7 Cl1 114.60(16) . .
C5 C6 C1 118.68(19) . .
C5 C6 H6 120.7 . .
C1 C6 H6 120.7 . .
C5 C4 C3 118.03(19) . .
C5 C4 H4 121.0 . .
C3 C4 H4 121.0 . .
C2A C1A C6A 117.62(18) . .
C2A C1A C7A 119.68(19) . .
C6A C1A C7A 122.69(18) . .
F2A C5A C6A 118.12(19) . .
F2A C5A C4A 118.67(19) . .
C6A C5A C4A 123.2(2) . .
C5A C4A C3A 118.19(19) . .
C5A C4A H4A 120.9 . .
C3A C4A H4A 120.9 . .
F1A C2A C3A 117.43(18) . .
F1A C2A C1A 119.98(18) . .
C3A C2A C1A 122.6(2) . .
O1A C7A C1A 127.2(2) . .
O1A C7A Cl1A 118.29(16) . .
C1A C7A Cl1A 114.46(17) . .
C2A C3A C4A 119.49(19) . .
C2A C3A H3A 120.3 . .
C4A C3A H3A 120.3 . .
C5A C6A C1A 118.90(19) . .
C5A C6A H6A 120.6 . .
C1A C6A H6A 120.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C7 1.774(2) .
F1 C2 1.349(2) .
F2 C5 1.356(2) .
O1 C7 1.187(3) .
C2 C3 1.375(3) .
C2 C1 1.393(3) .
C5 C6 1.374(3) .
C5 C4 1.380(3) .
C1 C6 1.399(3) .
C1 C7 1.482(3) .
C3 C4 1.386(3) .
C3 H3 0.9500 .
C6 H6 0.9500 .
C4 H4 0.9500 .
Cl1A C7A 1.784(2) .
F2A C5A 1.350(2) .
F1A C2A 1.347(2) .
O1A C7A 1.181(3) .
C1A C2A 1.396(3) .
C1A C6A 1.402(3) .
C1A C7A 1.483(3) .
C5A C6A 1.372(3) .
C5A C4A 1.380(3) .
C4A C3A 1.385(3) .
C4A H4A 0.9500 .
C2A C3A 1.372(3) .
C3A H3A 0.9500 .
C6A H6A 0.9500 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
F1 C2 C1 C6 179.5(2) . . . .
C3 C2 C1 C6 -0.1(4) . . . .
F1 C2 C1 C7 -1.7(4) . . . .
C3 C2 C1 C7 178.6(2) . . . .
F1 C2 C3 C4 179.4(2) . . . .
C1 C2 C3 C4 -0.9(4) . . . .
C2 C1 C7 O1 -17.3(4) . . . .
C6 C1 C7 O1 161.4(3) . . . .
C2 C1 C7 Cl1 163.0(2) . . . .
C6 C1 C7 Cl1 -18.3(3) . . . .
F2 C5 C6 C1 -179.9(2) . . . .
C4 C5 C6 C1 -0.2(4) . . . .
C2 C1 C6 C5 0.7(4) . . . .
C7 C1 C6 C5 -178.0(2) . . . .
F2 C5 C4 C3 178.8(2) . . . .
C6 C5 C4 C3 -0.9(4) . . . .
C2 C3 C4 C5 1.4(4) . . . .
F2A C5A C4A C3A 178.1(2) . . . .
C6A C5A C4A C3A -1.0(4) . . . .
C6A C1A C2A F1A 179.6(2) . . . .
C7A C1A C2A F1A -1.3(4) . . . .
C6A C1A C2A C3A -0.4(4) . . . .
C7A C1A C2A C3A 178.6(2) . . . .
C2A C1A C7A O1A -10.5(4) . . . .
C6A C1A C7A O1A 168.5(3) . . . .
C2A C1A C7A Cl1A 169.01(18) . . . .
C6A C1A C7A Cl1A -12.0(3) . . . .
F1A C2A C3A C4A 179.5(2) . . . .
C1A C2A C3A C4A -0.4(4) . . . .
C5A C4A C3A C2A 1.1(4) . . . .
F2A C5A C6A C1A -178.9(2) . . . .
C4A C5A C6A C1A 0.1(4) . . . .
C2A C1A C6A C5A 0.5(4) . . . .
C7A C1A C6A C5A -178.5(2) . . . .
