Crystal structures of racemic and enantiopure synephrine correlated with physicochemical properties from IR spectroscopy and thermal analysis
Fujii, Isao; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618014419

data_2021302
_publ_section_title
;
 Crystal structures of racemic and enantiopure synephrine correlated with
 physicochemical properties from IR spectroscopy and thermal analysis
;
_journal_coeditor_code           QF3019
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618014419
_journal_volume                  74
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C9 H13 N1 O2'
_chemical_formula_sum            'C9 H13 N O2'
_chemical_formula_weight         167.2
_chemical_name_systematic
;
4-[1-Hydroxy-2-(methylamino)ethyl]phenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5581(15)
_cell_length_b                   7.8144(18)
_cell_length_c                   17.137(5)
_cell_measurement_reflns_used    1029
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      25.7
_cell_volume                     878.2(4)
_computing_cell_refinement
;
<i>CrystalClear-SM Expert</i> (Rigaku, 2015)
;
_computing_data_collection
;
<i>CrystalClear-SM Expert</i> (Rigaku, 2015)
;
_computing_data_reduction
;
SORTAV (Blessing, 1995) and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>,
2008)
;
_computing_publication_material
;
PLATON (Spek, 2009),
WinGX (Farrugia, 2012) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al.</i>,  1994)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'quarter \C-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7138
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.207
_diffrn_reflns_theta_min         7.23
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>REQAB</i>; Rigaku, 1998)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.196
_refine_ls_abs_structure_details
;
Flack x determined using 590 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.06(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.17
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.17
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0659P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.081
_refine_ls_wR_factor_ref         0.098
_reflns_number_gt                1504
_reflns_number_total             1586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            qf3019sup1.cif
_cod_data_source_block           R-SYN
_cod_database_code               2021302
_cod_database_fobs_code          2021302