Crystal structures and hydrogen bonding in the anhydrous tryptaminium salts of the isomeric (2,4-dichlorophenoxy)acetic and (3,5-dichlorophenoxy)acetic acids
Smith, Graham; Lynch, Daniel E.; Acta Crystallographica Section E 71 (2015) 671–674; doi:10.1107/S205698901500907X

data_2240773
_publ_section_title
;
 Crystal structures and hydrogen bonding in the anhydrous tryptaminium
 salts of the isomeric (2,4-dichlorophenoxy)acetic and
 (3,5-dichlorophenoxy)acetic acids
;
_journal_coeditor_code           SJ5460
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              671
_journal_page_last               674
_journal_paper_doi               10.1107/S205698901500907X
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C10 H13 N2 +, C8 H5 Cl2 O3 -'
_chemical_formula_moiety         'C10 H13 N2 +, C8 H5 Cl2 O3 -'
_chemical_formula_sum            'C18 H18 Cl2 N2 O3'
_chemical_formula_weight         381.25
_chemical_name_common            'tryptaminium (2,4-dichlorophenoxy)acetate'
_chemical_name_systematic
;
2-(1<i>H</i>-Indol-3-yl)ethanaminium (2,4-dichlorophenoxy)acetate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 93.565(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9818(11)
_cell_length_b                   6.8899(7)
_cell_length_c                   14.6850(15)
_cell_measurement_reflns_used    940
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      23.99
_cell_measurement_theta_min      3.76
_cell_volume                     907.00(17)
_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
;
SHELX97 (Sheldrick, 2008) within WinGX (Farrugia, 2012)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al.</i>, 1993)
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0699
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3991
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.261
_refine_ls_abs_structure_details
;
Flack (1983)
;
_refine_ls_abs_structure_Flack   0.45(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0677
_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^)+(0.0918P)^2^+0.3461P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1868
_reflns_number_gt                2299
_reflns_number_total             2896
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sj5460sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2240773
_cod_database_fobs_code          2240773