Synthesis and anticonvulsant activity of phenoxyacetyl derivatives of amines, including aminoalkanols and amino acids.
Pańczyk, Katarzyna; Żelaszczyk, Dorota; Koczurkiewicz, Paulina; Słoczyńska, Karolina; Pękala, Elżbieta; Żesławska, Ewa; Nitek, Wojciech; Żmudzki, Paweł; Marona, Henryk; Waszkielewicz, Anna; MedChemComm 9 (2018) 1933–1948; doi:10.1039/c8md00430g

data_7122487
_publ_section_title
;
 Synthesis and anticonvulsant activity of phenoxyacetyl derivatives of
 amines, including aminoalkanols and amino acids.
;
_journal_issue                   11
_journal_name_full               MedChemComm
_journal_page_first              1933
_journal_page_last               1948
_journal_paper_doi               10.1039/c8md00430g
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H19 N O3'
_chemical_formula_sum            'C13 H19 N O3'
_chemical_formula_weight         237.29
_chemical_name_systematic
;
R-(-)-2-(2,6-dimethylphenoxy)-N-(1-hydroxypropan-2-yl)acetamide
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-03-26T21:33:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-03-26 deposited with the CCDC.
2018-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3307(4)
_cell_length_b                   20.5418(9)
_cell_length_c                   8.5970(4)
_cell_measurement_reflns_used    10755
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      71.421
_cell_measurement_theta_min      4.283
_cell_volume                     1294.59(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0393073
_diffrn_orient_matrix_UB_12      0.0697522
_diffrn_orient_matrix_UB_13      -0.0569339
_diffrn_orient_matrix_UB_21      0.0180619
_diffrn_orient_matrix_UB_22      0.0229841
_diffrn_orient_matrix_UB_23      0.1697151
_diffrn_orient_matrix_UB_31      0.2057612
_diffrn_orient_matrix_UB_32      -0.015308
_diffrn_orient_matrix_UB_33      -0.0040796
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19025
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.99
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.622
_diffrn_reflns_theta_min         4.305
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.7
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.557
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.137
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.4
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 982 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.21(11)
_refine_ls_extinction_coef       0.0067(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0952
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0968P)^2^+2.5980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.237
_refine_ls_wR_factor_ref         0.2388
_reflns_number_gt                2452
_reflns_number_total             2497
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8md00430g2.cif
_cod_data_source_block           aw_3
_cod_depositor_comments
'Adding full bibliography for 7122487--7122489.cif.'
_cod_database_code               7122487
_shelx_estimated_absorpt_t_min   0.696
_shelx_estimated_absorpt_t_max   0.91
_shelx_res_checksum              2077