#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/61/2016181.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_2016181
loop_
_publ_author_name
'Janik, Alicja'
'Chyra, Anna'
'Stadnicka, Katarzyna'
_publ_section_title
;
 N-Acetyl-<small>L</small>-tyrosine methyl ester monohydrate at
 293 and 123K
;
_journal_coeditor_code           BM3032
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o572
_journal_page_last               o575
_journal_paper_doi               10.1107/S0108270107038413
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H15 N O4, H2 O'
_chemical_formula_moiety         'C12 H15 N O4, H2 O'
_chemical_formula_sum            'C12 H17 N O5'
_chemical_formula_weight         255.27
_chemical_name_systematic
;
N-Acetyl-L-tyrosine methyl ester monohydrate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1118(2)
_cell_length_b                   12.9364(3)
_cell_length_c                   14.1538(4)
_cell_measurement_reflns_used    2646
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      33.142
_cell_measurement_theta_min      0.998
_cell_volume                     1302.17(6)
_computing_cell_refinement       'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_data_reduction
'DENZO and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
PLATON (Spek, 2003), ORTEP-3 for Windows (Farrugia, 1997) and
Mercury (Version
1.4; Macrae et al.,  2006)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ο scans at chi = 55 deg'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10167
_diffrn_reflns_theta_full        33.14
_diffrn_reflns_theta_max         33.14
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_correction_T_min  0.9605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'HKL DENZO and Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0317
_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)+(0.0426P)²+0.2619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                2605
_reflns_number_total             2790
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm3032.cif
_cod_data_source_block           Ib
_cod_database_code               2016181
_cod_database_fobs_code          2016181
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
N N1 0.71157(15) 0.48699(7) 0.65787(7) 0.01325(17) Uani d . 1
H H1 0.794(3) 0.4817(15) 0.7039(14) 0.028(5) Uiso d . 1
C C1 0.77991(17) 0.38398(8) 0.51734(8) 0.01321(19) Uani d . 1
O O1 0.77403(18) 0.30426(6) 0.56186(7) 0.0240(2) Uani d . 1
C C2 0.77647(16) 0.49188(8) 0.56094(8) 0.01177(18) Uani d . 1
H H2 0.6892 0.5367 0.5237 0.014 Uiso calc R 1
O O2 0.79393(15) 0.38950(7) 0.42407(6) 0.01828(17) Uani d . 1
C C3 0.97621(16) 0.53788(8) 0.55674(8) 0.01389(19) Uani d . 1
H H3A 1.0611 0.4955 0.5964 0.017 Uiso calc R 1
H H3B 1.0226 0.5345 0.4909 0.017 Uiso calc R 1
C C4 0.98391(16) 0.64882(8) 0.59029(8) 0.01260(18) Uani d . 1
C C5 0.89806(17) 0.72820(8) 0.53906(8) 0.0151(2) Uani d . 1
H H5 0.8327 0.7121 0.4824 0.018 Uiso calc R 1
C C6 1.07879(18) 0.67465(8) 0.67320(8) 0.0156(2) Uani d . 1
H H6 1.1384 0.6217 0.7088 0.019 Uiso calc R 1
C C7 0.90651(17) 0.83047(8) 0.56958(9) 0.0149(2) Uani d . 1
H H7 0.8476 0.8835 0.5338 0.018 Uiso calc R 1
C C8 1.08802(19) 0.77652(8) 0.70499(8) 0.0164(2) Uani d . 1
H H8 1.1527 0.7926 0.7618 0.020 Uiso calc R 1
C C9 1.00179(16) 0.85473(8) 0.65288(8) 0.01301(18) Uani d . 1
O O9 1.01535(14) 0.95384(6) 0.68652(6) 0.01733(17) Uani d . 1
H H9 0.967(4) 1.0001(19) 0.6502(18) 0.049(7) Uiso d . 1
C C10 0.53053(17) 0.46497(8) 0.67793(8) 0.0144(2) Uani d . 1
O O10 0.40919(13) 0.45748(8) 0.61595(7) 0.02064(18) Uani d . 1
C C11 0.4846(2) 0.44935(11) 0.78070(9) 0.0221(2) Uani d . 1
H H11A 0.4006 0.5047 0.8021 0.027 Uiso calc R 1
H H11B 0.6008 0.4509 0.8179 0.027 Uiso calc R 1
H H11C 0.4225 0.3824 0.7891 0.027 Uiso calc R 1
C C12 0.8035(2) 0.29199(10) 0.37386(10) 0.0257(3) Uani d . 1
H H12A 0.8135 0.3052 0.3059 0.031 Uiso calc R 1
H H12B 0.6895 0.2517 0.3866 0.031 Uiso calc R 1
H H12C 0.9139 0.2531 0.3952 0.031 Uiso calc R 1
O O5 0.34119(15) 0.41298(7) 0.43062(7) 0.02093(19) Uani d . 1
H H5B 0.360(4) 0.4303(17) 0.4900(19) 0.048(7) Uiso d . 1
H H5A 0.330(4) 0.352(2) 0.4296(19) 0.049(7) Uiso 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 0.0033 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_publ_flag
C10 N1 C2 120.80(10) ?
C10 N1 H1 118.0(10) ?
C2 N1 H1 120.0(10) ?
O1 C1 O2 124.60(10) ?
O1 C1 C2 124.70(10) ?
O2 C1 C2 110.80(10) ?
N1 C2 C1 110.40(10) y
N1 C2 C3 110.30(10) y
C1 C2 C3 108.80(10) y
N1 C2 H2 109.1 ?
C1 C2 H2 109.1 ?
C3 C2 H2 109.1 ?
C1 O2 C12 116.40(10) y
C4 C3 C2 112.80(10) ?
C4 C3 H3A 109.0 ?
C2 C3 H3A 109.0 ?
C4 C3 H3B 109.0 ?
C2 C3 H3B 109.0 ?
H3A C3 H3B 107.8 ?
C6 C4 C5 118.20(10) ?
C6 C4 C3 120.60(10) ?
C5 C4 C3 121.20(10) ?
C7 C5 C4 121.20(10) ?
C7 C5 H5 119.4 ?
C4 C5 H5 119.4 ?
C8 C6 C4 121.40(10) ?
C8 C6 H6 119.3 ?
C4 C6 H6 119.3 ?
C5 C7 C9 119.80(10) ?
C5 C7 H7 120.1 ?
C9 C7 H7 120.1 ?
C9 C8 C6 119.60(10) ?
C9 C8 H8 120.2 ?
C6 C8 H8 120.2 ?
O9 C9 C8 117.70(10) ?
O9 C9 C7 122.50(10) ?
C8 C9 C7 119.80(10) ?
C9 O9 H9 114(2) ?
O10 C10 N1 122.30(10) ?
O10 C10 C11 121.70(10) ?
N1 C10 C11 116.00(10) ?
C10 C11 H11A 109.5 ?
C10 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C10 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
O2 C12 H12A 109.5 ?
O2 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
O2 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
H5A O5 H5B 107(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C10 1.349(2) y
N1 C2 1.449(2) y
N1 H1 0.88(2) ?
C1 O1 1.2090(10) y
C1 O2 1.3260(10) ?
C1 C2 1.5260(10) y
C2 C3 1.541(2) y
C2 H2 1.0000 ?
O2 C12 1.4490(10) y
C3 C4 1.513(2) ?
C3 H3A 0.9900 ?
C3 H3B 0.9900 ?
C4 C6 1.394(2) ?
C4 C5 1.398(2) ?
C5 C7 1.393(2) ?
C5 H5 0.9500 ?
C6 C8 1.394(2) ?
C6 H6 0.9500 ?
C7 C9 1.396(2) ?
C7 H7 0.9500 ?
C8 C9 1.394(2) ?
C8 H8 0.9500 ?
C9 O9 1.3710(10) ?
O9 H9 0.86(3) ?
C10 O10 1.234(2) y
C10 C11 1.504(2) ?
C11 H11A 0.9800 ?
C11 H11B 0.9800 ?
C11 H11C 0.9800 ?
C12 H12A 0.9800 ?
C12 H12B 0.9800 ?
C12 H12C 0.9800 ?
O5 H5B 0.88(3) ?
O5 H5A 0.79(3) ?
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
_geom_hbond_publ_flag
O9 H9 O5 3_566 0.86(3) 1.83(3) 2.6930(10) 173(3) y
N1 H1 O9 4_746 0.88(2) 2.09(2) 2.9680(10) 174(2) y
O5 H5A O1 3_456 0.79(3) 2.07(3) 2.8530(10) 173(3) y
O5 H5B O10 . 0.88(3) 1.85(3) 2.7290(10) 176(2) y
C3 H3A O10 1_655 0.99 2.54 3.356(2) 140 y
C8 H8 O1 4_756 0.95 2.55 3.462(2) 160 y
C11 H11A O5 2_565 0.98 2.72 3.612(2) 151 ?
C12 H12C O10 3_556 0.98 2.73 3.317(2) 119 ?
C5 H5 Cg1 3_466 0.95 2.84 3.65(4) 144 y
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_publ_flag
C10 N1 C2 C1 -70.30(10) ?
C10 N1 C2 C3 169.40(10) ?
O1 C1 C2 N1 -16.5(2) y
O2 C1 C2 N1 164.80(10) y
O1 C1 C2 C3 104.70(10) y
O2 C1 C2 C3 -74.10(10) y
O1 C1 O2 C12 -0.3(2) ?
C2 C1 O2 C12 178.50(10) ?
N1 C2 C3 C4 -64.00(10) ?
C1 C2 C3 C4 174.80(10) ?
C2 C3 C4 C6 112.90(10) ?
C2 C3 C4 C5 -67.60(10) ?
C6 C4 C5 C7 0.0(2) ?
C3 C4 C5 C7 -179.50(10) ?
C5 C4 C6 C8 0.3(2) ?
C3 C4 C6 C8 179.70(10) ?
C4 C5 C7 C9 -0.2(2) ?
C4 C6 C8 C9 -0.4(2) ?
C6 C8 C9 O9 -179.60(10) ?
C6 C8 C9 C7 0.2(2) ?
C5 C7 C9 O9 179.90(10) ?
C5 C7 C9 C8 0.1(2) ?
C2 N1 C10 O10 -6.8(2) ?
C2 N1 C10 C11 172.90(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654071
