#------------------------------------------------------------------------------
#$Date: 2016-05-31 10:54:22 +0300 (Tue, 31 May 2016) $
#$Revision: 183168 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/89/7118967.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_7118967
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          262.5
_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                94.6130(10)
_cell_angle_beta                 104.2750(10)
_cell_angle_gamma                115.9060(10)
_cell_formula_units_Z            2
_cell_length_a                   6.85900(10)
_cell_length_b                   7.20060(10)
_cell_length_c                   8.03650(10)
_cell_measurement_reflns_used    6234
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.68
_cell_volume                     337.850(9)
_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      140(2)
_diffrn_measured_fraction_theta_full 0.785
_diffrn_measured_fraction_theta_max 0.721
_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  0.0093
_diffrn_reflns_av_unetI/netI     0.0059
_diffrn_reflns_Laue_measured_fraction_full 0.785
_diffrn_reflns_Laue_measured_fraction_max 0.721
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6690
_diffrn_reflns_point_group_measured_fraction_full 0.785
_diffrn_reflns_point_group_measured_fraction_max 0.721
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_min         2.678
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_description       block
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0254
_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)+(0.0351P)²+0.1592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0726
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1190
_reflns_number_total             1210
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc02535h2.cif
_cod_data_source_block           23dfbc
_cod_original_cell_volume        337.849(9)
_cod_database_code               7118967
_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 0.68906(7) 0.77056(8) 0.93339(4) 0.03450(18) Uani 1 1 d . . . . .
F2 F -0.14086(16) 0.78161(17) 0.37637(11) 0.0258(3) Uani 1 1 d . . . . .
F1 F 0.02139(16) 0.79670(16) 0.71317(11) 0.0239(3) Uani 1 1 d . . . . .
O1 O 0.3104(2) 0.7355(2) 0.96205(14) 0.0347(4) Uani 1 1 d . . . . .
C1 C 0.3324(3) 0.7513(3) 0.67157(15) 0.0151(4) Uani 1 1 d . . . . .
C3 C 0.0521(3) 0.7649(3) 0.43122(17) 0.0173(4) Uani 1 1 d . . . . .
C4 C 0.1579(3) 0.7385(3) 0.31362(16) 0.0185(4) Uani 1 1 d . . . . .
H4 H 0.0980 0.7338 0.1925 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4419(3) 0.7262(3) 0.55236(16) 0.0164(4) Uani 1 1 d . . . . .
H6 H 0.5773 0.7142 0.5931 0.020 Uiso 1 1 calc R U . . .
C5 C 0.3548(3) 0.7188(3) 0.37554(16) 0.0181(4) Uani 1 1 d . . . . .
H5 H 0.4299 0.7001 0.2960 0.022 Uiso 1 1 calc R U . . .
C2 C 0.1359(3) 0.7716(3) 0.60806(16) 0.0157(4) Uani 1 1 d . . . . .
C7 C 0.4118(3) 0.7497(3) 0.86031(17) 0.0200(4) Uani 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'
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
C2 C1 C6 118.26(11) . .
C2 C1 C7 118.84(12) . .
C6 C1 C7 122.86(12) . .
F2 C3 C4 120.56(12) . .
F2 C3 C2 117.73(12) . .
C4 C3 C2 121.70(12) . .
C3 C4 C5 118.63(12) . .
C3 C4 H4 120.7 . .
C5 C4 H4 120.7 . .
C5 C6 C1 120.68(12) . .
C5 C6 H6 119.7 . .
C1 C6 H6 119.7 . .
C6 C5 C4 120.51(12) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
F1 C2 C3 117.74(11) . .
F1 C2 C1 122.05(11) . .
C3 C2 C1 120.22(12) . .
O1 C7 C1 126.73(13) . .
O1 C7 Cl1 118.86(10) . .
C1 C7 Cl1 114.40(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C7 1.7805(15) .
F2 C3 1.3494(14) .
F1 C2 1.3375(14) .
O1 C7 1.1807(18) .
C1 C2 1.3942(17) .
C1 C6 1.4002(18) .
C1 C7 1.4826(17) .
C3 C4 1.3732(19) .
C3 C2 1.3835(18) .
C4 C5 1.3921(18) .
C4 H4 0.9500 .
C6 C5 1.3857(17) .
C6 H6 0.9500 .
C5 H5 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
F2 C3 C4 C5 -179.05(15) . . . .
C2 C3 C4 C5 -0.2(3) . . . .
C2 C1 C6 C5 -0.9(3) . . . .
C7 C1 C6 C5 176.91(15) . . . .
C1 C6 C5 C4 0.7(3) . . . .
C3 C4 C5 C6 -0.2(3) . . . .
F2 C3 C2 F1 -0.8(2) . . . .
C4 C3 C2 F1 -179.65(16) . . . .
F2 C3 C2 C1 178.84(15) . . . .
C4 C3 C2 C1 -0.1(3) . . . .
C6 C1 C2 F1 -179.81(15) . . . .
C7 C1 C2 F1 2.2(2) . . . .
C6 C1 C2 C3 0.6(3) . . . .
C7 C1 C2 C3 -177.33(15) . . . .
C2 C1 C7 O1 11.0(3) . . . .
C6 C1 C7 O1 -166.86(18) . . . .
C2 C1 C7 Cl1 -169.32(13) . . . .
C6 C1 C7 Cl1 12.8(2) . . . .
