#------------------------------------------------------------------------------
#$Date: 2016-05-31 10:54:22 +0300 (Tue, 31 May 2016) $
#$Revision: 183168 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/89/7118966.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_7118966
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 H5 Cl O'
_chemical_formula_weight         140.56
_chemical_melting_point          273.5
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                90
_cell_angle_beta                 93.566(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4704(5)
_cell_length_b                   3.9581(2)
_cell_length_c                   22.3439(12)
_cell_measurement_reflns_used    4203
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.39
_cell_measurement_theta_min      2.83
_cell_volume                     659.40(7)
_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      200(2)
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.910
_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  0.0126
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7678
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.695
_diffrn_reflns_theta_min         2.826
_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_transmission_factor_max   0.856
_exptl_transmission_factor_min   0.856
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0514
_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)+(0.0691P)²+0.4288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1544
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1398
_reflns_number_total             1555
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc02535h2.cif
_cod_data_source_block           bc
_cod_database_code               7118966
_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   0.869
_shelx_estimated_absorpt_t_max   0.869
loop_
_space_group_symop_operation_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_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 0.17545(9) 0.48504(19) 0.44790(3) 0.0662(3) Uani 1 1 d . . . . .
O1 O 0.1158(2) 0.4075(7) 0.33536(10) 0.0746(7) Uani 1 1 d . . . . .
C7 C 0.2265(3) 0.3579(6) 0.37415(10) 0.0434(5) Uani 1 1 d . . . . .
C1 C 0.4033(2) 0.2018(5) 0.36839(9) 0.0348(4) Uani 1 1 d . . . . .
C2 C 0.4396(3) 0.0884(6) 0.31189(10) 0.0408(5) Uani 1 1 d . . . . .
H2 H 0.3518 0.1112 0.2795 0.049 Uiso 1 1 calc R U . . .
C3 C 0.6037(3) -0.0582(6) 0.30239(12) 0.0507(6) Uani 1 1 d . . . . .
H3 H 0.6287 -0.1360 0.2636 0.061 Uiso 1 1 calc R U . . .
C4 C 0.7303(3) -0.0909(6) 0.34936(13) 0.0555(7) Uani 1 1 d . . . . .
H4 H 0.8427 -0.1925 0.3430 0.067 Uiso 1 1 calc R U . . .
C6 C 0.5316(3) 0.1676(6) 0.41576(11) 0.0460(5) Uani 1 1 d . . . . .
H6 H 0.5070 0.2431 0.4548 0.055 Uiso 1 1 calc R U . . .
C5 C 0.6950(3) 0.0231(7) 0.40567(14) 0.0581(7) Uani 1 1 d . . . . .
H5 H 0.7838 0.0020 0.4378 0.070 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'
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
O1 C7 C1 126.8(2) . .
O1 C7 Cl1 116.85(18) . .
C1 C7 Cl1 116.32(15) . .
C2 C1 C6 119.94(19) . .
C2 C1 C7 116.37(17) . .
C6 C1 C7 123.69(19) . .
C1 C2 C3 120.1(2) . .
C1 C2 H2 119.9 . .
C3 C2 H2 119.9 . .
C4 C3 C2 119.8(2) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C3 C4 C5 120.3(2) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
C5 C6 C1 119.4(2) . .
C5 C6 H6 120.3 . .
C1 C6 H6 120.3 . .
C4 C5 C6 120.5(2) . .
C4 C5 H5 119.8 . .
C6 C5 H5 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C7 1.787(2) .
O1 C7 1.177(3) .
C7 C1 1.471(3) .
C1 C2 1.383(3) .
C1 C6 1.389(3) .
C2 C3 1.385(3) .
C2 H2 0.9500 .
C3 C4 1.374(4) .
C3 H3 0.9500 .
C4 C5 1.378(4) .
C4 H4 0.9500 .
C6 C5 1.379(3) .
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
O1 C7 C1 C2 -3.1(4) . . . .
Cl1 C7 C1 C2 176.96(16) . . . .
O1 C7 C1 C6 176.4(3) . . . .
Cl1 C7 C1 C6 -3.6(3) . . . .
C6 C1 C2 C3 -0.2(3) . . . .
C7 C1 C2 C3 179.3(2) . . . .
C1 C2 C3 C4 0.1(3) . . . .
C2 C3 C4 C5 -0.3(4) . . . .
C2 C1 C6 C5 0.6(3) . . . .
C7 C1 C6 C5 -178.8(2) . . . .
C3 C4 C5 C6 0.7(4) . . . .
C1 C6 C5 C4 -0.9(4) . . . .
