2-(2-Acetylamino-5-chlorophenyl)-2,2-difluoroethanoic acid and 2-(2-acetylamino-5-methylphenyl)-2,2-difluoroethanoic acid, and 2-(2-acetylaminophenyl)-2,2-difluoro-<i>N</i>-phenylacetamide and 2-(2-acetylaminophenyl)-<i>N</i>-(4-chlorophenyl)-2,2-difluoroacetamide: examples of variation in molecular packing and hydrogen-bonding motif induced by substituent change
Boechat, Nubia; Maciel, Lindalva C.; Wardell, Solange M. S. V.; Skakle, Janet M. S.; Howie, R. Alan; Acta Crystallographica Section C 61 (2005) o270–o275; doi:10.1107/S0108270105007547

data_2014829
_publ_section_title
;
 2-(2-Acetylamino-5-chlorophenyl)-2,2-difluoroethanoic acid and
 2-(2-acetylamino-5-methylphenyl)-2,2-difluoroethanoic acid, and
 2-(2-acetylaminophenyl)-2,2-difluoro-<i>N</i>-phenylacetamide and
 2-(2-acetylaminophenyl)-<i>N</i>-(4-chlorophenyl)-2,2-difluoroacetamide:
 examples of variation in molecular packing and hydrogen-bonding motif
 induced by substituent change
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o270
_journal_page_last               o275
_journal_paper_doi               10.1107/S0108270105007547
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H13 Cl F2 N2 O2'
_chemical_formula_moiety         'C16 H13 Cl F2 N2 O2'
_chemical_formula_sum            'C16 H13 Cl F2 N2 O2'
_chemical_formula_weight         338.73
_chemical_melting_point          .445E-305
_chemical_name_systematic
;
2-(2-acetylaminophenyl)-N-(4-chlorophenyl)-2,2-difluoroacetamide
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.0100(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.5777(10)
_cell_length_b                   9.8176(6)
_cell_length_c                   9.6962(6)
_cell_measurement_reflns_used    3620
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      31.20
_cell_measurement_theta_min      2.41
_cell_volume                     1569.41(17)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_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  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15368
_diffrn_reflns_theta_full        32.55
_diffrn_reflns_theta_max         32.55
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         5629
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0478P)^2^+0.3392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                2824
_reflns_number_total             5629
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd1371.cif
_cod_data_source_block           IV
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom and difmap' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014829
_cod_database_fobs_code          2014829