#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/27/2012755.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_2012755
loop_
_publ_author_name
'Jankowska, Elżbieta'
'Gilski, Mirosław'
'Jaskólski, Mariusz'
'Grzonka, Zbigniew'
'Łankiewicz, Leszek'
_publ_section_title
O-Benzyl-N-tert-butoxycarbonyl-N-methyl-<small>L</small>-tyrosine
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o353
_journal_page_last               o354
_journal_paper_doi               10.1107/S0108270102007114
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C22 H27 N O5'
_chemical_formula_moiety         'C22 H27 N O5'
_chemical_formula_sum            'C22 H27 N O5'
_chemical_formula_weight         385.45
_chemical_name_systematic
;
N-t-butoxycarbonyl-N-methyl-(O-benzyl)-L-tyrosine
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.346(2)
_cell_length_b                   11.413(2)
_cell_length_c                   19.493(4)
_cell_measurement_reflns_used    6728
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.58
_cell_measurement_theta_min      3.41
_cell_volume                     2079.2(7)
_computing_cell_refinement       'KM4CCD Software'
_computing_data_collection
'KM4CCD Software (Kuma Diffraction, 1995--1999)'
_computing_data_reduction        'KM4CCD Software'
_computing_molecular_graphics
'Stereochemical Workstation Operation Manual (Siemens, 1989)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Kuma CCD'
_diffrn_measurement_method       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  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11736
_diffrn_reflns_theta_full        29.58
_diffrn_reflns_theta_max         29.58
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.343
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.341
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.341
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=  1/[σ²(Fo²)+(0.0369P)²+0.4413P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                2602
_reflns_number_total             3067
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd1196.cif
_cod_data_source_block           I
_cod_database_code               2012755
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_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
_atom_site_type_symbol
C1 0.4823(3) 0.0363(2) 0.80810(13) 0.0188(5) Uani d . 1 . . C
C2 0.4612(3) 0.1673(2) 0.82199(13) 0.0166(5) Uani d . 1 . . C
H2 0.5026 0.2109 0.7835 0.020 Uiso d R 1 . . H
C3 0.5429(3) 0.2009(2) 0.88737(14) 0.0200(6) Uani d . 1 . . C
H3A 0.6439 0.1853 0.8803 0.024 Uiso d R 1 . . H
H3B 0.5104 0.1512 0.9246 0.024 Uiso d R 1 . . H
C4 0.5248(3) 0.3281(2) 0.90884(13) 0.0174(5) Uani d . 1 . . C
C5 0.5415(3) 0.4196(2) 0.86279(14) 0.0194(5) Uani d . 1 . . C
H5 0.5590 0.4029 0.8168 0.023 Uiso d R 1 . . H
C6 0.5328(3) 0.5370(2) 0.88385(14) 0.0204(6) Uani d . 1 . . C
H6 0.5424 0.5974 0.8522 0.024 Uiso d R 1 . . H
C7 0.5089(3) 0.5615(2) 0.95287(13) 0.0165(5) Uani d . 1 . . C
C8 0.4907(3) 0.4705(2) 0.99939(13) 0.0188(5) Uani d . 1 . . C
H8 0.4733 0.4869 1.0454 0.023 Uiso d R 1 . . H
C9 0.4980(3) 0.3555(2) 0.97697(13) 0.0196(5) Uani d . 1 . . C
H9 0.4847 0.2952 1.0084 0.024 Uiso d R 1 . . H
C10 0.5179(3) 0.7707(2) 0.93510(13) 0.0213(5) Uani d . 1 . . C
H10A 0.6080 0.7664 0.9105 0.026 Uiso d R 1 . . H
H10B 0.4405 0.7732 0.9020 0.026 Uiso d R 1 . . H
C11 0.5141(3) 0.8770(2) 0.98061(13) 0.0195(5) Uani d . 1 . . C
C12 0.3840(3) 0.9273(2) 0.99931(15) 0.0214(5) Uani d . 1 . . C
H12 0.2992 0.8981 0.9811 0.026 Uiso d R 1 . . H
C13 0.3811(3) 1.0210(2) 1.04485(15) 0.0224(6) Uani d . 1 . . C
H13 0.2940 1.0546 1.0570 0.027 Uiso d R 1 . . H
C14 0.5075(3) 1.0641(2) 1.07221(13) 0.0216(5) Uani d . 1 . . C
H14 0.5051 1.1266 1.1028 0.026 Uiso d R 1 . . H
C15 0.6366(3) 1.0143(2) 1.05368(15) 0.0243(6) Uani d . 1 . . C
H15 0.7215 1.0435 1.0718 0.029 Uiso d R 1 . . H
C16 0.6402(3) 0.9211(2) 1.00808(15) 0.0236(6) Uani d . 1 . . C
H16 0.7274 0.8876 0.9961 0.028 Uiso d R 1 . . H
C17 0.2292(3) 0.1548(2) 0.88562(13) 0.0198(5) Uani d . 1 . . C
H17A 0.2939 0.1197 0.9179 0.024 Uiso d R 1 . . H
H17B 0.1593 0.0980 0.8716 0.024 Uiso d R 1 . . H
H17C 0.1819 0.2202 0.9067 0.024 Uiso d R 1 . . H
C18 0.2456(3) 0.2483(2) 0.77139(13) 0.0165(5) Uani d . 1 . . C
C19 0.0050(3) 0.3014(2) 0.72621(13) 0.0210(5) Uani d . 1 . . C
C20 0.0290(4) 0.2414(3) 0.65794(15) 0.0342(7) Uani d . 1 . . C
H20A 0.0162 0.1584 0.6633 0.041 Uiso d R 1 . . H
H20B -0.0383 0.2706 0.6249 0.041 Uiso d R 1 . . H
H20C 0.1246 0.2570 0.6423 0.041 Uiso d R 1 . . H
C21 -0.1406(3) 0.2701(3) 0.75539(16) 0.0302(7) Uani d . 1 . . C
H21A -0.1500 0.1864 0.7571 0.036 Uiso d R 1 . . H
H21B -0.1496 0.3017 0.8008 0.036 Uiso d R 1 . . H
H21C -0.2143 0.3021 0.7266 0.036 Uiso d R 1 . . H
C22 0.0229(4) 0.4334(2) 0.72242(18) 0.0329(7) Uani d . 1 . . C
H22A 0.0064 0.4665 0.7670 0.040 Uiso d R 1 . . H
H22B 0.1184 0.4517 0.7078 0.040 Uiso d R 1 . . H
H22C -0.0445 0.4656 0.6904 0.040 Uiso d R 1 . . H
O2 0.3872(2) -0.03413(17) 0.80441(11) 0.0266(5) Uani d . 1 . . O
O1 0.6198(2) 0.01092(18) 0.80018(12) 0.0286(5) Uani d . 1 . . O
H1 0.630(4) -0.061(3) 0.7952(18) 0.036(10) Uiso d . 1 . . H
O3 0.3122(2) 0.28603(15) 0.72172(9) 0.0207(4) Uani d . 1 . . O
O5 0.5022(2) 0.67162(15) 0.98023(9) 0.0206(4) Uani d . 1 . . O
O4 0.1034(2) 0.25426(17) 0.77968(9) 0.0212(4) Uani d . 1 . . O
N1 0.3088(2) 0.19508(18) 0.82567(11) 0.0169(4) Uani d . 1 . . N
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
O2 C1 O1 124.3(2) y
O2 C1 C2 124.7(2) y
O1 C1 C2 111.0(2) y
N1 C2 C1 110.2(2) y
N1 C2 C3 112.9(2) y
C1 C2 C3 109.1(2) y
N1 C2 H2 108.2 ?
C1 C2 H2 108.1 ?
C3 C2 H2 108.2 ?
C4 C3 C2 114.3(2) y
C4 C3 H3A 108.8 ?
C2 C3 H3A 108.7 ?
C4 C3 H3B 108.5 ?
C2 C3 H3B 108.7 ?
H3A C3 H3B 107.6 ?
C5 C4 C9 118.1(2) no
C5 C4 C3 121.9(2) y
C9 C4 C3 119.9(2) y
C4 C5 C6 121.6(2) no
C4 C5 H5 119.2 ?
C6 C5 H5 119.2 ?
C7 C6 C5 119.0(2) no
C7 C6 H6 120.5 ?
C5 C6 H6 120.5 ?
O5 C7 C8 115.3(2) y
O5 C7 C6 124.7(2) y
C8 C7 C6 120.0(2) no
C9 C8 C7 119.8(2) no
C9 C8 H8 120.3 ?
C7 C8 H8 120.0 ?
C8 C9 C4 121.6(2) no
C8 C9 H9 119.1 ?
C4 C9 H9 119.3 ?
O5 C10 C11 105.71(19) y
O5 C10 H10A 110.5 ?
C11 C10 H10A 110.6 ?
O5 C10 H10B 110.7 ?
C11 C10 H10B 110.5 ?
H10A C10 H10B 108.7 ?
C16 C11 C12 119.3(2) no
C16 C11 C10 120.0(2) y
C12 C11 C10 120.5(2) y
C13 C12 C11 120.1(3) no
C13 C12 H12 120.1 ?
C11 C12 H12 119.8 ?
C14 C13 C12 120.1(3) no
C14 C13 H13 120.1 ?
C12 C13 H13 119.8 ?
C15 C14 C13 119.8(2) no
C15 C14 H14 120.3 ?
C13 C14 H14 119.9 ?
C14 C15 C16 120.3(3) no
C14 C15 H15 119.8 ?
C16 C15 H15 119.9 ?
C15 C16 C11 120.3(3) no
C15 C16 H16 119.9 ?
C11 C16 H16 119.8 ?
N1 C17 H17A 109.6 ?
N1 C17 H17B 109.4 ?
H17A C17 H17B 109.5 ?
N1 C17 H17C 109.4 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
O3 C18 O4 125.4(2) y
O3 C18 N1 123.4(2) y
O4 C18 N1 111.1(2) y
O4 C19 C20 111.1(2) y
O4 C19 C21 101.9(2) y
C20 C19 C21 110.9(2) y
O4 C19 C22 108.9(2) y
C20 C19 C22 113.0(3) y
C21 C19 C22 110.6(3) y
C19 C20 H20A 109.4 ?
C19 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C19 C20 H20C 109.4 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C19 C21 H21A 109.2 ?
C19 C21 H21B 109.6 ?
H21A C21 H21B 109.5 ?
C19 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
C19 C22 H22A 109.2 ?
C19 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
C19 C22 H22C 109.8 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
C1 O1 H1 110(3) ?
C7 O5 C10 118.62(19) y
C18 O4 C19 123.1(2) y
C18 N1 C17 123.0(2) y
C18 N1 C2 118.9(2) y
C17 N1 C2 117.9(2) y
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
C1 O2 . 1.201(3) y
C1 O1 . 1.327(3) y
C1 C2 . 1.531(3) y
C2 N1 . 1.462(3) y
C2 C3 . 1.534(4) y
C2 H2 . 0.9800 ?
C3 C4 . 1.520(3) y
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.386(4) no
C4 C9 . 1.387(4) no
C5 C6 . 1.403(4) no
C5 H5 . 0.9302 ?
C6 C7 . 1.392(3) no
C6 H6 . 0.9300 ?
C7 O5 . 1.367(3) y
C7 C8 . 1.389(4) no
C8 C9 . 1.385(4) no
C8 H8 . 0.9300 ?
C9 H9 . 0.93 ?
C10 O5 . 1.440(3) y
C10 C11 . 1.504(3) y
C10 H10A . 0.9701 ?
C10 H10B . 0.9700 ?
C11 C16 . 1.389(4) no
C11 C12 . 1.393(4) no
C12 C13 . 1.390(4) no
C12 H12 . 0.9300 ?
C13 C14 . 1.386(4) no
C13 H13 . 0.9300 ?
C14 C15 . 1.383(4) no
C14 H14 . 0.9300 ?
C15 C16 . 1.386(4) no
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 N1 . 1.459(3) y
C17 H17A . 0.9598 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9601 ?
C18 O3 . 1.229(3) y
C18 O4 . 1.340(3) y
C18 N1 . 1.356(3) y
C19 O4 . 1.491(3) y
C19 C20 . 1.514(4) y
C19 C21 . 1.517(4) y
C19 C22 . 1.518(4) y
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9599 ?
C21 H21C . 0.9601 ?
C22 H22A . 0.9599 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
O1 H1 . 0.83(4) ?
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
O2 C1 C2 N1 -3.6(4) ?
O1 C1 C2 N1 175.9(2) y
O2 C1 C2 C3 120.9(3) ?
O1 C1 C2 C3 -59.5(3) ?
N1 C2 C3 C4 -54.3(3) y
C1 C2 C3 C4 -177.2(2) ?
C2 C3 C4 C5 -48.6(4) y
C2 C3 C4 C9 134.8(3) ?
C9 C4 C5 C6 0.4(4) ?
C3 C4 C5 C6 -176.3(2) ?
C4 C5 C6 C7 1.0(4) ?
C5 C6 C7 O5 178.0(3) ?
C5 C6 C7 C8 -1.6(4) ?
O5 C7 C8 C9 -178.9(2) ?
C6 C7 C8 C9 0.7(4) ?
C7 C8 C9 C4 0.7(4) ?
C5 C4 C9 C8 -1.2(4) ?
C3 C4 C9 C8 175.5(2) ?
O5 C10 C11 C16 90.0(3) ?
O5 C10 C11 C12 -85.7(3) y
C16 C11 C12 C13 0.2(4) ?
C10 C11 C12 C13 175.9(2) ?
C11 C12 C13 C14 -0.5(4) ?
C12 C13 C14 C15 0.5(4) ?
C13 C14 C15 C16 -0.3(4) ?
C14 C15 C16 C11 0.0(4) ?
C12 C11 C16 C15 0.0(4) ?
C10 C11 C16 C15 -175.7(3) ?
C8 C7 O5 C10 -179.1(2) ?
C6 C7 O5 C10 1.3(4) y
C11 C10 O5 C7 -176.9(2) y
O3 C18 O4 C19 4.3(4) y
N1 C18 O4 C19 -176.0(2) ?
C20 C19 O4 C18 52.8(3) ?
C21 C19 O4 C18 171.0(2) ?
C22 C19 O4 C18 -72.2(3) ?
O3 C18 N1 C17 177.5(2) ?
O4 C18 N1 C17 -2.2(3) ?
O3 C18 N1 C2 -8.0(4) ?
O4 C18 N1 C2 172.3(2) y
C1 C2 N1 C18 -103.2(3) y
C3 C2 N1 C18 134.5(2) ?
C1 C2 N1 C17 71.6(3) ?
C3 C2 N1 C17 -50.7(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5374171
