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#$Date: 2022-11-17 11:16:21 +0200 (Thu, 17 Nov 2022) $
#$Revision: 279349 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106129.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_8106129
loop_
_publ_author_name
'Wang, Wan-Wan'
'Chen, Xing-Ying'
'Wu, Wei-Na'
_publ_section_title
;
 Crystal Structure of 3-((3-hydroxybenzyl)ammonio)-3-phenylpropanoate,
 C16H17NO3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              289
_journal_page_last               290
_journal_paper_doi               10.1515/ncrs-2017-0289
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.31
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3470(3)
_cell_length_b                   7.9347(2)
_cell_length_c                   17.0947(4)
_cell_measurement_reflns_used    1254
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.89
_cell_measurement_theta_min      2.12
_cell_volume                     1403.48(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7284
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0427
_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)+(0.0510P)²+0.0074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                2601
_reflns_number_total             3348
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0289_suppl.cif
_cod_data_source_block           z
_cod_original_sg_symbol_H-M      Pna21
_cod_database_code               8106129
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.14440(17) -0.0150(2) 0.26586(11) 0.0366(4) Uani 1 1 d . . .
C2 C 0.08533(18) 0.1201(2) 0.30297(11) 0.0380(4) Uani 1 1 d . . .
H2A H 0.0166 0.1001 0.3367 0.046 Uiso 1 1 calc R . .
C3 C 0.12621(17) 0.2833(2) 0.29094(11) 0.0375(4) Uani 1 1 d . . .
C4 C 0.2304(2) 0.3131(3) 0.24119(13) 0.0484(5) Uani 1 1 d . . .
H4A H 0.2595 0.4223 0.2325 0.058 Uiso 1 1 calc R . .
C5 C 0.2897(2) 0.1780(3) 0.20494(14) 0.0541(6) Uani 1 1 d . . .
H5A H 0.3595 0.1975 0.1719 0.065 Uiso 1 1 calc R . .
C6 C 0.2481(2) 0.0156(3) 0.21663(14) 0.0474(5) Uani 1 1 d . . .
H6A H 0.2894 -0.0735 0.1916 0.057 Uiso 1 1 calc R . .
C7 C 0.05659(18) 0.4242(2) 0.33172(13) 0.0405(4) Uani 1 1 d . . .
H7A H 0.0146 0.4938 0.2926 0.049 Uiso 1 1 calc R . .
H7B H -0.0105 0.3761 0.3645 0.049 Uiso 1 1 calc R . .
C8 C 0.23146(17) 0.4463(2) 0.43628(12) 0.0337(4) Uani 1 1 d . . .
H8A H 0.2931 0.3815 0.4048 0.040 Uiso 1 1 calc R . .
C9 C 0.30710(18) 0.5827(3) 0.47988(11) 0.0405(4) Uani 1 1 d . . .
H9A H 0.2461 0.6580 0.5050 0.049 Uiso 1 1 calc R . .
H9B H 0.3578 0.5294 0.5207 0.049 Uiso 1 1 calc R . .
C10 C 0.39666(17) 0.6861(2) 0.42905(13) 0.0397(5) Uani 1 1 d . . .
C11 C 0.16529(16) 0.3254(2) 0.49145(11) 0.0353(4) Uani 1 1 d . . .
C12 C 0.2129(2) 0.1623(2) 0.49785(14) 0.0499(5) Uani 1 1 d . . .
H12A H 0.2784 0.1268 0.4644 0.060 Uiso 1 1 calc R . .
C13 C 0.1647(3) 0.0531(3) 0.55272(16) 0.0624(7) Uani 1 1 d . . .
H13A H 0.1986 -0.0551 0.5569 0.075 Uiso 1 1 calc R . .
C14 C 0.0667(2) 0.1028(3) 0.60151(14) 0.0583(6) Uani 1 1 d . . .
H14A H 0.0346 0.0287 0.6389 0.070 Uiso 1 1 calc R . .
C15 C 0.0162(2) 0.2615(3) 0.59512(13) 0.0541(6) Uani 1 1 d . . .
H15A H -0.0516 0.2943 0.6275 0.065 Uiso 1 1 calc R . .
C16 C 0.06539(19) 0.3730(3) 0.54073(12) 0.0448(5) Uani 1 1 d . . .
H16A H 0.0312 0.4811 0.5371 0.054 Uiso 1 1 calc R . .
N1 N 0.14055(15) 0.53358(19) 0.38107(9) 0.0343(3) Uani 1 1 d D . .
O1 O 0.10327(13) -0.17578(17) 0.27564(10) 0.0471(4) Uani 1 1 d D . .
O2 O 0.38455(13) 0.67574(18) 0.35614(8) 0.0459(4) Uani 1 1 d . . .
O3 O 0.47816(16) 0.7752(2) 0.46356(11) 0.0624(5) Uani 1 1 d . . .
H1 H 0.0311(18) -0.171(4) 0.3003(17) 0.094 Uiso 1 1 d D . .
H1A H 0.182(3) 0.600(3) 0.3504(16) 0.094 Uiso 1 1 d D . .
H1B H 0.091(3) 0.604(3) 0.4057(17) 0.094 Uiso 1 1 d D . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 C6 118.90(17) . .
O1 C1 C2 122.18(17) . .
C6 C1 C2 118.92(17) . .
C3 C2 C1 121.51(17) . .
C3 C2 H2A 119.2 . .
C1 C2 H2A 119.2 . .
C2 C3 C4 119.22(19) . .
C2 C3 C7 118.89(17) . .
C4 C3 C7 121.89(18) . .
C5 C4 C3 119.08(19) . .
C5 C4 H4A 120.5 . .
C3 C4 H4A 120.5 . .
C6 C5 C4 121.5(2) . .
C6 C5 H5A 119.2 . .
C4 C5 H5A 119.2 . .
C5 C6 C1 119.7(2) . .
C5 C6 H6A 120.1 . .
C1 C6 H6A 120.1 . .
N1 C7 C3 114.64(15) . .
N1 C7 H7A 108.6 . .
C3 C7 H7A 108.6 . .
N1 C7 H7B 108.6 . .
C3 C7 H7B 108.6 . .
H7A C7 H7B 107.6 . .
N1 C8 C11 113.68(14) . .
N1 C8 C9 107.47(14) . .
C11 C8 C9 112.16(16) . .
N1 C8 H8A 107.8 . .
C11 C8 H8A 107.8 . .
C9 C8 H8A 107.8 . .
C10 C9 C8 114.68(17) . .
C10 C9 H9A 108.6 . .
C8 C9 H9A 108.6 . .
C10 C9 H9B 108.6 . .
C8 C9 H9B 108.6 . .
H9A C9 H9B 107.6 . .
O3 C10 O2 124.99(19) . .
O3 C10 C9 116.72(19) . .
O2 C10 C9 118.28(17) . .
C16 C11 C12 118.07(17) . .
C16 C11 C8 123.03(16) . .
C12 C11 C8 118.69(17) . .
C13 C12 C11 120.9(2) . .
C13 C12 H12A 119.5 . .
C11 C12 H12A 119.5 . .
C12 C13 C14 120.2(2) . .
C12 C13 H13A 119.9 . .
C14 C13 H13A 119.9 . .
C15 C14 C13 119.9(2) . .
C15 C14 H14A 120.0 . .
C13 C14 H14A 120.0 . .
C14 C15 C16 120.2(2) . .
C14 C15 H15A 119.9 . .
C16 C15 H15A 119.9 . .
C15 C16 C11 120.6(2) . .
C15 C16 H16A 119.7 . .
C11 C16 H16A 119.7 . .
C7 N1 C8 116.88(14) . .
C7 N1 H1A 108(2) . .
C8 N1 H1A 111(2) . .
C7 N1 H1B 108(2) . .
C8 N1 H1B 111(2) . .
H1A N1 H1B 101(3) . .
C1 O1 H1 107(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.355(2) .
C1 C6 1.385(3) .
C1 C2 1.388(3) .
C2 C3 1.377(3) .
C2 H2A 0.9300 .
C3 C4 1.393(3) .
C3 C7 1.501(3) .
C4 C5 1.382(3) .
C4 H4A 0.9300 .
C5 C6 1.373(3) .
C5 H5A 0.9300 .
C6 H6A 0.9300 .
C7 N1 1.490(2) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 N1 1.502(2) .
C8 C11 1.509(3) .
C8 C9 1.529(3) .
C8 H8A 0.9800 .
C9 C10 1.512(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 O3 1.249(2) .
C10 O2 1.255(2) .
C11 C16 1.386(3) .
C11 C12 1.389(3) .
C12 C13 1.371(3) .
C12 H12A 0.9300 .
C13 C14 1.371(4) .
C13 H13A 0.9300 .
C14 C15 1.368(3) .
C14 H14A 0.9300 .
C15 C16 1.381(3) .
C15 H15A 0.9300 .
C16 H16A 0.9300 .
N1 H1A 0.860(10) .
N1 H1B 0.866(10) .
O1 H1 0.858(10) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.858(10) 1.792(10) 2.6486(19) 176(3) 4_455
N1 H1A O2 0.860(10) 2.18(3) 2.798(2) 128(3) .
N1 H1B O3 0.866(10) 1.807(11) 2.667(2) 172(3) 4_465
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 -178.37(18) . . . .
C6 C1 C2 C3 1.0(3) . . . .
C1 C2 C3 C4 -0.9(3) . . . .
C1 C2 C3 C7 178.87(18) . . . .
C2 C3 C4 C5 0.2(3) . . . .
C7 C3 C4 C5 -179.5(2) . . . .
C3 C4 C5 C6 0.3(3) . . . .
C4 C5 C6 C1 -0.1(3) . . . .
O1 C1 C6 C5 178.9(2) . . . .
C2 C1 C6 C5 -0.5(3) . . . .
C2 C3 C7 N1 123.63(18) . . . .
C4 C3 C7 N1 -56.6(3) . . . .
N1 C8 C9 C10 -66.0(2) . . . .
C11 C8 C9 C10 168.38(16) . . . .
C8 C9 C10 O3 -166.38(18) . . . .
C8 C9 C10 O2 13.2(3) . . . .
N1 C8 C11 C16 -56.0(2) . . . .
C9 C8 C11 C16 66.2(2) . . . .
N1 C8 C11 C12 129.29(19) . . . .
C9 C8 C11 C12 -108.5(2) . . . .
C16 C11 C12 C13 -1.7(3) . . . .
C8 C11 C12 C13 173.4(2) . . . .
C11 C12 C13 C14 1.1(4) . . . .
C12 C13 C14 C15 0.5(4) . . . .
C13 C14 C15 C16 -1.4(3) . . . .
C14 C15 C16 C11 0.7(3) . . . .
C12 C11 C16 C15 0.8(3) . . . .
C8 C11 C16 C15 -174.03(19) . . . .
C3 C7 N1 C8 -48.2(2) . . . .
C11 C8 N1 C7 -55.5(2) . . . .
C9 C8 N1 C7 179.74(15) . . . .
