Two-dimensional hydrogen-bonded polymers in the crystal structures of the ammonium salts of phenoxyacetic acid, (4-fluorophenoxy)acetic acid and (4-chloro-2-methylphenoxy)acetic acid
Smith, Graham; Acta Crystallographica Section E 70 (2014) 528–532; doi:10.1107/S160053681402488X

data_2240222
_publ_section_title
;
 Two-dimensional hydrogen-bonded polymers in the crystal structures of the
 ammonium salts of phenoxyacetic acid, (4-fluorophenoxy)acetic acid and
 (4-chloro-2-methylphenoxy)acetic acid
;
_journal_coeditor_code           SU5018
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              528
_journal_page_last               532
_journal_paper_doi               10.1107/S160053681402488X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'N H4 +, C9 H8 Cl N O3 -, 0.5H2 O'
_chemical_formula_moiety         'H4 N +, C9 H8 Cl N O3 -, 0.5(H2 O)'
_chemical_formula_sum            'C9 H13 Cl N O3.5'
_chemical_formula_weight         226.65
_chemical_name_common
'ammonium (4-chloro-2-methylphenoxy)acetate hemihydrate'
_chemical_name_systematic
;
Ammonium (4-chloro-2-methylphenoxy)acetate hemihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.575(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   38.0396(9)
_cell_length_b                   4.4560(8)
_cell_length_c                   12.944(5)
_cell_measurement_reflns_used    1819
_cell_measurement_temperature    200.0(10)
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      4.38
_cell_volume                     2123.5(9)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      200.0(10)
_diffrn_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-S CCD-detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6215
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.281
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0409P)^2^+1.4504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                1771
_reflns_number_total             2087
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            su5018sup1.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C9 H13 Cl N O3.50'
_cod_database_code               2240222
_cod_database_fobs_code          2240222