#------------------------------------------------------------------------------
#$Date: 2016-05-21 04:39:40 +0300 (Sat, 21 May 2016) $
#$Revision: 183063 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/33/1543347.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1543347
loop_
_publ_author_name
'Zhang, Xiaohui'
'Yu, Yuzhen'
'Li, Zhanjun'
'Li, Wen'
_publ_section_title
;
 <small>D</small>-({-})-2-Azaniumyl-2-(4-hydroxyphenyl)acetate: an
 orthorhombic polymorph
;
_journal_coeditor_code           SJ4032
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x160768
_journal_paper_doi               10.1107/S2414314616007689
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C8 H9 N O3'
_chemical_formula_moiety         'C8 H9 N O3'
_chemical_formula_sum            'C8 H9 N O3'
_chemical_formula_weight         167.16
_chemical_name_systematic
;
D-(-)-2-Azaniumyl-2-(4-hydroxyphenyl)acetate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.83624(17)
_cell_length_b                   8.4245(3)
_cell_length_c                   17.0381(5)
_cell_measurement_reflns_used    2415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7890
_cell_measurement_theta_min      5.1900
_cell_volume                     837.72(5)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2012)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent Xcalibur Eos Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3647
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.932
_diffrn_reflns_theta_min         5.192
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.165
_refine_ls_abs_structure_details
;
Flack x
determined using 616 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   0.03(11)
_refine_ls_extinction_coef       0.076(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0615P)²+0.1107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                1570
_reflns_number_total             1613
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj4032sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        837.72(4)
_cod_database_code               1543347
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.8218(4) 0.6736(2) 0.67248(12) 0.0355(5) Uani d 1
H H1 0.8643 0.7484 0.6351 0.043 Uiso calc 1
C C2 0.7995(4) 0.7195(3) 0.75027(12) 0.0369(5) Uani d 1
H H2 0.8267 0.8242 0.7648 0.044 Uiso calc 1
C C3 0.7367(4) 0.6088(3) 0.80590(11) 0.0329(5) Uani d 1
C C4 0.6892(5) 0.4543(3) 0.78378(12) 0.0424(6) Uani d 1
H H4 0.6415 0.3806 0.8210 0.051 Uiso calc 1
C C5 0.7130(4) 0.4097(2) 0.70566(12) 0.0355(5) Uani d 1
H H5 0.6822 0.3055 0.6911 0.043 Uiso calc 1
C C6 0.7817(3) 0.5177(2) 0.64934(10) 0.0264(4) Uani d 1
C C7 0.8146(3) 0.4675(2) 0.56526(10) 0.0250(4) Uani d 1
H H7 0.7981 0.3519 0.5622 0.030 Uiso calc 1
C C8 1.0554(3) 0.5127(2) 0.53564(11) 0.0270(4) Uani d 1
N N1 0.6394(3) 0.5416(2) 0.51327(9) 0.0276(4) Uani d 1
H H1A 0.6596 0.5079 0.4642 0.033 Uiso calc 1
H H1B 0.6540 0.6467 0.5148 0.033 Uiso calc 1
H H1C 0.5000 0.5145 0.5296 0.033 Uiso calc 1
O O1 0.7186(4) 0.6457(2) 0.88365(8) 0.0478(5) Uani d 1
H H1D 0.7565 0.7384 0.8905 0.072 Uiso calc 1
O O2 1.0735(3) 0.62801(19) 0.49116(10) 0.0396(4) Uani d 1
O O3 1.2178(3) 0.4283(2) 0.56048(10) 0.0445(5) Uani d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 H1 119.4
C2 C1 C6 121.21(19)
C6 C1 H1 119.4
C1 C2 H2 120.2
C3 C2 C1 119.6(2)
C3 C2 H2 120.2
C2 C3 C4 120.14(18)
O1 C3 C2 122.26(19)
O1 C3 C4 117.60(18)
C3 C4 H4 120.2
C3 C4 C5 119.67(19)
C5 C4 H4 120.2
C4 C5 H5 119.5
C6 C5 C4 121.1(2)
C6 C5 H5 119.5
C1 C6 C7 120.89(17)
C5 C6 C1 118.26(18)
C5 C6 C7 120.84(18)
C6 C7 H7 108.5
C6 C7 C8 111.00(15)
C8 C7 H7 108.5
N1 C7 C6 111.12(16)
N1 C7 H7 108.5
N1 C7 C8 109.12(14)
O2 C8 C7 118.21(16)
O2 C8 O3 125.84(18)
O3 C8 C7 115.94(16)
C7 N1 H1A 109.5
C7 N1 H1B 109.5
C7 N1 H1C 109.5
H1A N1 H1B 109.5
H1A N1 H1C 109.5
H1B N1 H1C 109.5
C3 O1 H1D 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 H1 0.9300
C1 C2 1.387(3)
C1 C6 1.391(3)
C2 H2 0.9300
C2 C3 1.379(3)
C3 C4 1.383(3)
C3 O1 1.365(2)
C4 H4 0.9300
C4 C5 1.390(3)
C5 H5 0.9300
C5 C6 1.382(3)
C6 C7 1.506(3)
C7 H7 0.9800
C7 C8 1.541(2)
C7 N1 1.490(2)
C8 O2 1.237(2)
C8 O3 1.258(3)
N1 H1A 0.8900
N1 H1B 0.8900
N1 H1C 0.8900
O1 H1D 0.8200
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O1 2_664 0.89 2.02 2.838(2) 153.0
N1 H1B O2 3_466 0.89 1.96 2.811(2) 160.0
N1 H1C O3 1_455 0.89 1.87 2.759(2) 172.0
O1 H1D O3 4_756 0.82 1.81 2.591(2) 158.3
C2 H2 Cg 4_556 0.93 3.165 3.913(2) 138.8
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 C2 C3 C4 -2.0(4)
C1 C2 C3 O1 178.0(2)
C1 C6 C7 C8 53.4(2)
C1 C6 C7 N1 -68.2(2)
C2 C1 C6 C5 1.6(3)
C2 C1 C6 C7 -177.8(2)
C2 C3 C4 C5 2.3(4)
C3 C4 C5 C6 -0.6(4)
C4 C5 C6 C1 -1.4(4)
C4 C5 C6 C7 178.0(2)
C5 C6 C7 C8 -126.0(2)
C5 C6 C7 N1 112.4(2)
C6 C1 C2 C3 0.1(4)
C6 C7 C8 O2 -104.3(2)
C6 C7 C8 O3 74.7(2)
N1 C7 C8 O2 18.4(2)
N1 C7 C8 O3 -162.55(18)
O1 C3 C4 C5 -177.8(2)

_cod_database_fobs_code 1543347
