#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/85/2228517.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228517
loop_
_publ_author_name
'Zhang, Fang'
'Liang, Wen-De'
'Li, Gong-Xing'
'Jiang, Wang'
'Xiao, Zhu-Ping'
_publ_section_title
;
 Ethyl 2-(3-amino-4-hydroxyphenyl)acetate
;
_journal_coeditor_code           PV2339
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3069
_journal_paper_doi               10.1107/S1600536810044399
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H13 N O3'
_chemical_formula_moiety         'C10 H13 N O3'
_chemical_formula_sum            'C10 H13 N O3'
_chemical_formula_weight         195.21
_chemical_name_systematic
;
Ethyl 2-(3-amino-4-hydroxyphenyl)acetate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.23(3)
_cell_angle_beta                 104.96(3)
_cell_angle_gamma                90.41(3)
_cell_formula_units_Z            4
_cell_length_a                   8.5940(17)
_cell_length_b                   10.142(2)
_cell_length_c                   12.043(2)
_cell_measurement_reflns_used    2097
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.92
_cell_measurement_theta_min      2.35
_cell_volume                     1002.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3857
_diffrn_reflns_theta_full        25.17
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0786
_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/[σ²(Fo²)+(0.0847P)²+0.7608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1833
_refine_ls_wR_factor_ref         0.2132
_reflns_number_gt                2121
_reflns_number_total             3598
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2339.cif
_cod_data_source_block           I
_cod_original_cell_volume        1002.6(3)
_cod_database_code               2228517
_cod_database_fobs_code          2228517
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.0536(4) 0.8579(3) 0.9060(3) 0.0860(11) Uani d . 1 . .
O O2 1.2035(3) 0.7342(3) 0.8128(3) 0.0690(9) Uani d . 1 . .
O O3 0.9659(3) 0.2198(3) 0.4667(3) 0.0611(8) Uani d . 1 . .
H H3A 1.0353 0.1671 0.4878 0.092 Uiso calc R 1 . .
N N1 0.7667(5) 0.3994(3) 0.4283(3) 0.063 Uani d . 1 . .
H H1A 0.6993 0.4586 0.4059 0.075 Uiso calc R 1 . .
H H1B 0.7774 0.3314 0.3797 0.075 Uiso calc R 1 . .
C C1 1.1307(7) 1.0449(5) 0.8320(6) 0.102(2) Uani d . 1 . .
H H1C 1.2096 1.1172 0.8466 0.153 Uiso calc R 1 . .
H H1D 1.0260 1.0801 0.8263 0.153 Uiso calc R 1 . .
H H1E 1.1306 0.9893 0.7604 0.153 Uiso calc R 1 . .
C C2 1.1679(6) 0.9708(5) 0.9218(5) 0.0779(15) Uani d . 1 . .
H H2A 1.1697 1.0281 0.9939 0.093 Uiso calc R 1 . .
H H2B 1.2750 0.9377 0.9283 0.093 Uiso calc R 1 . .
C C3 1.0796(5) 0.7484(4) 0.8404(4) 0.0513(10) Uani d . 1 . .
C C4 0.9484(5) 0.6448(4) 0.8233(4) 0.0655(13) Uani d . 1 . .
H H4A 0.8454 0.6861 0.8036 0.079 Uiso calc R 1 . .
H H4B 0.9581 0.6112 0.8962 0.079 Uiso calc R 1 . .
C C5 0.9492(5) 0.5276(4) 0.7290(4) 0.0500(10) Uani d . 1 . .
C C6 1.0634(5) 0.4308(4) 0.7533(4) 0.0514(10) Uani d . 1 . .
H H6A 1.1342 0.4357 0.8267 0.062 Uiso calc R 1 . .
C C7 1.0690(5) 0.3282(4) 0.6664(4) 0.0531(10) Uani d . 1 . .
H H7A 1.1455 0.2644 0.6825 0.064 Uiso calc R 1 . .
C C8 0.9663(4) 0.3164(3) 0.5569(3) 0.0430(9) Uani d . 1 . .
C C9 0.8494(4) 0.4121(3) 0.5322(3) 0.0424(9) Uani d . 1 . .
C C10 0.8459(5) 0.5164(4) 0.6213(4) 0.0498(10) Uani d . 1 . .
H H10A 0.7697 0.5806 0.6061 0.060 Uiso calc R 1 . .
O O4 0.3631(3) 0.5329(2) 0.1330(2) 0.0541(7) Uani d . 1 . .
O O5 0.5351(4) 0.6553(3) 0.2847(3) 0.0739(10) Uani d . 1 . .
O O6 0.4558(4) 1.2663(3) 0.4366(3) 0.0727(10) Uani d . 1 . .
H H6B 0.5107 1.3115 0.4082 0.087 Uiso calc R 1 . .
N N2 0.2886(4) 1.1022(4) 0.5184(3) 0.0628(10) Uani d . 1 . .
H H2C 0.2324 1.0498 0.5447 0.075 Uiso calc R 1 . .
H H2D 0.3165 1.1816 0.5548 0.075 Uiso calc R 1 . .
C C11 0.4060(6) 0.3167(4) 0.0431(4) 0.0734(14) Uani d . 1 . .
H H11A 0.4722 0.2412 0.0527 0.110 Uiso calc R 1 . .
H H11B 0.4119 0.3505 -0.0263 0.110 Uiso calc R 1 . .
H H11C 0.2963 0.2901 0.0369 0.110 Uiso calc R 1 . .
C C12 0.4636(5) 0.4217(4) 0.1442(4) 0.0642(12) Uani d . 1 . .
H H12A 0.4625 0.3866 0.2148 0.077 Uiso calc R 1 . .
H H12B 0.5737 0.4501 0.1496 0.077 Uiso calc R 1 . .
C C13 0.4116(5) 0.6431(4) 0.2094(3) 0.0465(9) Uani d . 1 . .
C C14 0.2909(5) 0.7474(4) 0.1919(4) 0.0570(11) Uani d . 1 . .
H H14A 0.1973 0.7178 0.2141 0.068 Uiso calc R 1 . .
H H14B 0.2568 0.7527 0.1094 0.068 Uiso calc R 1 . .
C C15 0.3408(4) 0.8849(3) 0.2550(3) 0.0454(9) Uani d . 1 . .
C C16 0.4443(5) 0.9678(4) 0.2213(4) 0.0559(11) Uani d . 1 . .
H H16A 0.4852 0.9373 0.1584 0.067 Uiso calc R 1 . .
C C17 0.4866(5) 1.0952(4) 0.2809(3) 0.0508(10) Uani d . 1 . .
H H17A 0.5512 1.1512 0.2548 0.061 Uiso calc R 1 . .
C C18 0.4349(4) 1.1409(3) 0.3781(3) 0.0374(8) Uani d . 1 . .
C C19 0.3347(4) 1.0583(3) 0.4161(3) 0.0403(8) Uani d . 1 . .
C C20 0.2923(4) 0.9312(3) 0.3547(3) 0.0443(9) Uani d . 1 . .
H H20A 0.2290 0.8746 0.3812 0.053 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O1 C2 . . 116.0(3) ?
C8 O3 H3A . . 109.5 ?
C9 N1 H1A . . 120.0 ?
C9 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
C2 C1 H1C . . 109.5 ?
C2 C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
C2 C1 H1E . . 109.5 ?
H1C C1 H1E . . 109.5 ?
H1D C1 H1E . . 109.5 ?
C1 C2 O1 . . 113.0(5) ?
C1 C2 H2A . . 109.0 ?
O1 C2 H2A . . 109.0 ?
C1 C2 H2B . . 109.0 ?
O1 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
O2 C3 O1 . . 121.8(4) ?
O2 C3 C4 . . 126.7(4) ?
O1 C3 C4 . . 110.9(3) ?
C3 C4 C5 . . 114.2(3) ?
C3 C4 H4A . . 108.7 ?
C5 C4 H4A . . 108.7 ?
C3 C4 H4B . . 108.7 ?
C5 C4 H4B . . 108.7 ?
H4A C4 H4B . . 107.6 ?
C10 C5 C6 . . 119.1(4) ?
C10 C5 C4 . . 122.0(4) ?
C6 C5 C4 . . 118.8(4) ?
C7 C6 C5 . . 118.8(4) ?
C7 C6 H6A . . 120.6 ?
C5 C6 H6A . . 120.6 ?
C8 C7 C6 . . 122.6(4) ?
C8 C7 H7A . . 118.7 ?
C6 C7 H7A . . 118.7 ?
O3 C8 C7 . . 126.1(4) ?
O3 C8 C9 . . 114.9(4) ?
C7 C8 C9 . . 119.0(3) ?
N1 C9 C10 . . 126.8(4) ?
N1 C9 C8 . . 115.3(4) ?
C10 C9 C8 . . 117.7(4) ?
C5 C10 C9 . . 122.7(4) ?
C5 C10 H10A . . 118.6 ?
C9 C10 H10A . . 118.6 ?
C13 O4 C12 . . 117.4(3) ?
C18 O6 H6B . . 109.5 ?
C19 N2 H2C . . 120.0 ?
C19 N2 H2D . . 120.0 ?
H2C N2 H2D . . 120.0 ?
C12 C11 H11A . . 109.5 ?
C12 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C12 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O4 C12 C11 . . 110.2(4) ?
O4 C12 H12A . . 109.6 ?
C11 C12 H12A . . 109.6 ?
O4 C12 H12B . . 109.6 ?
C11 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
O5 C13 O4 . . 124.2(4) ?
O5 C13 C14 . . 124.3(3) ?
O4 C13 C14 . . 111.5(3) ?
C13 C14 C15 . . 117.7(3) ?
C13 C14 H14A . . 107.9 ?
C15 C14 H14A . . 107.9 ?
C13 C14 H14B . . 107.9 ?
C15 C14 H14B . . 107.9 ?
H14A C14 H14B . . 107.2 ?
C20 C15 C16 . . 117.7(3) ?
C20 C15 C14 . . 120.4(3) ?
C16 C15 C14 . . 121.8(4) ?
C17 C16 C15 . . 120.3(4) ?
C17 C16 H16A . . 119.8 ?
C15 C16 H16A . . 119.8 ?
C18 C17 C16 . . 121.2(4) ?
C18 C17 H17A . . 119.4 ?
C16 C17 H17A . . 119.4 ?
O6 C18 C17 . . 126.4(3) ?
O6 C18 C19 . . 113.6(3) ?
C17 C18 C19 . . 119.6(3) ?
C20 C19 C18 . . 118.4(3) ?
C20 C19 N2 . . 121.9(3) ?
C18 C19 N2 . . 119.6(3) ?
C19 C20 C15 . . 122.6(3) ?
C19 C20 H20A . . 118.7 ?
C15 C20 H20A . . 118.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 . 1.324(5) ?
O1 C2 . 1.462(6) ?
O2 C3 . 1.199(4) ?
O3 C8 . 1.353(4) ?
O3 H3A . 0.8200 ?
N1 C9 . 1.257(5) ?
N1 H1A . 0.8600 ?
N1 H1B . 0.8600 ?
C1 C2 . 1.376(7) ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
C1 H1E . 0.9600 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.489(5) ?
C4 C5 . 1.523(5) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C10 . 1.359(6) ?
C5 C6 . 1.400(6) ?
C6 C7 . 1.377(5) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.372(6) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.408(5) ?
C9 C10 . 1.401(5) ?
C10 H10A . 0.9300 ?
O4 C13 . 1.331(4) ?
O4 C12 . 1.426(5) ?
O5 C13 . 1.198(5) ?
O6 C18 . 1.350(4) ?
O6 H6B . 0.8200 ?
N2 C19 . 1.405(5) ?
N2 H2C . 0.8600 ?
N2 H2D . 0.8600 ?
C11 C12 . 1.474(6) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.485(6) ?
C14 C15 . 1.491(5) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C20 . 1.391(5) ?
C15 C16 . 1.391(5) ?
C16 C17 . 1.382(5) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.379(5) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.398(5) ?
C19 C20 . 1.386(5) ?
C20 H20A . 0.9300 ?
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 H1B O2 2_766 0.86 2.37 3.097(5) 143.1
N2 H2D O5 2_676 0.86 2.42 3.222(5) 154.6
O3 H3A N2 1_645 0.82 2.23 2.978(5) 151.5
O6 H6B N1 1_565 0.82 2.31 3.015(5) 144.6
C10 H10A O6 2_676 0.93 2.49 3.414(5) 174.0
N1 H1B O3 . 0.86 2.12 2.517(5) 107.6
N2 H2D O6 . 0.86 2.33 2.641(4) 101.8
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 O1 C2 C1 . . . . 83.7(6) ?
C2 O1 C3 O2 . . . . 12.7(7) ?
C2 O1 C3 C4 . . . . -175.5(4) ?
O2 C3 C4 C5 . . . . -21.0(7) ?
O1 C3 C4 C5 . . . . 167.7(4) ?
C3 C4 C5 C10 . . . . -101.7(5) ?
C3 C4 C5 C6 . . . . 76.3(5) ?
C10 C5 C6 C7 . . . . 1.0(5) ?
C4 C5 C6 C7 . . . . -177.0(3) ?
C5 C6 C7 C8 . . . . -0.5(6) ?
C6 C7 C8 O3 . . . . 179.0(3) ?
C6 C7 C8 C9 . . . . -0.5(5) ?
O3 C8 C9 N1 . . . . -3.8(4) ?
C7 C8 C9 N1 . . . . 175.7(3) ?
O3 C8 C9 C10 . . . . -178.7(3) ?
C7 C8 C9 C10 . . . . 0.8(5) ?
C6 C5 C10 C9 . . . . -0.6(5) ?
C4 C5 C10 C9 . . . . 177.3(3) ?
N1 C9 C10 C5 . . . . -174.5(4) ?
C8 C9 C10 C5 . . . . -0.3(5) ?
C13 O4 C12 C11 . . . . -171.1(3) ?
C12 O4 C13 O5 . . . . 1.6(6) ?
C12 O4 C13 C14 . . . . -176.5(3) ?
O5 C13 C14 C15 . . . . 13.4(6) ?
O4 C13 C14 C15 . . . . -168.5(3) ?
C13 C14 C15 C20 . . . . -102.0(5) ?
C13 C14 C15 C16 . . . . 74.0(5) ?
C20 C15 C16 C17 . . . . -4.7(6) ?
C14 C15 C16 C17 . . . . 179.2(4) ?
C15 C16 C17 C18 . . . . 3.5(6) ?
C16 C17 C18 O6 . . . . -173.4(4) ?
C16 C17 C18 C19 . . . . -1.5(6) ?
O6 C18 C19 C20 . . . . 173.8(3) ?
C17 C18 C19 C20 . . . . 0.9(5) ?
O6 C18 C19 N2 . . . . -10.3(5) ?
C17 C18 C19 N2 . . . . 176.8(3) ?
C18 C19 C20 C15 . . . . -2.4(5) ?
N2 C19 C20 C15 . . . . -178.2(4) ?
C16 C15 C20 C19 . . . . 4.2(6) ?
C14 C15 C20 C19 . . . . -179.6(3) ?
