The effect of Cl···π interactions on the conformations of 4-chloro-5-(2-phenoxyethoxy)phthalonitrile and 4-chloro-5-[2-(pentafluorophenoxy)ethoxy]phthalonitrile
Hori, Akiko; Inoue, Yuta; Yuge, Hidetaka; Acta Crystallographica Section C 67 (2011) o154–o156; doi:10.1107/S0108270111008675

data_2018062
_publ_section_title
;
 The effect of Cl&#x00B7;&#x00B7;&#x00B7;\p interactions on the
 conformations of 4-chloro-5-(2-phenoxyethoxy)phthalonitrile and
 4-chloro-5-[2-(pentafluorophenoxy)ethoxy]phthalonitrile
;
_journal_coeditor_code           GD3379
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o154
_journal_page_last               o156
_journal_paper_doi               10.1107/S0108270111008675
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H6 Cl F5 N2 O2'
_chemical_formula_moiety         'C16 H6 Cl F5 N2 O2'
_chemical_formula_sum            'C16 H6 Cl F5 N2 O2'
_chemical_formula_weight         388.68
_chemical_name_common
;
4-chloro-5-[2-(pentafluorophenoxy)ethoxy]phthalonitrile
;
_chemical_name_systematic
;
4-chloro-5-[2-(pentafluorophenoxy)ethoxy]benzene-1,2-dicarbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.544(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8272(13)
_cell_length_b                   13.319(3)
_cell_length_c                   19.380(4)
_cell_measurement_reflns_used    5920
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.69
_cell_measurement_theta_min      2.61
_cell_volume                     1494.3(6)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w'
_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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16533
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_correction_T_min  0.9253
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0382P)^2^+1.0883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0876
_reflns_number_gt                2890
_reflns_number_total             3408
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3379.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018062
_cod_database_fobs_code          2018062