#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/01/2010185.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_2010185
loop_
_publ_author_name
'Mackay, M.F.'
'McLeish, M.J.'
'Campbell, M.'
_publ_section_title
;
 Two nitrogen-containing analogues of chorismic acid
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1734
_journal_page_last               1738
_journal_paper_doi               10.1107/S010827019400212X
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C13 H23 N1 O5'
_chemical_formula_sum            'C13 H23 N O5'
_chemical_formula_weight         273.3
_chemical_name_systematic
;
Methyl 3-[(tert-butyloxycarbonyl)amino]-4-hydroxy-cyclohexane-1-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.0
_cell_angle_beta                 99.510(10)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   14.2140(10)
_cell_length_b                   6.5930(10)
_cell_length_c                   16.5430(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    291.0(10)
_cell_measurement_theta_max      40
_cell_measurement_theta_min      22
_cell_volume                     1529.0(3)
_computing_cell_refinement       'Rigaku-AFC software'
_computing_data_collection       'Rigaku-AFC software'
_computing_data_reduction        'Rigaku-AFC software'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'Xtal3.0 (Hall & Stewart, 1990)'
_computing_structure_refinement  SHELX76
_computing_structure_solution    'SHELX76 (Sheldrick, 1976)'
_diffrn_ambient_temperature      291.0(10)
_diffrn_measurement_device       'Rigaku-AFC diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         xray_tube
_diffrn_radiation_type           'Copper K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_av_sigmaI/netI    0
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2685
_diffrn_reflns_theta_max         65.0
_diffrn_reflns_theta_min         4.5
_diffrn_standards_decay_%        <1.5
_diffrn_standards_interval_count 50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.72
_exptl_absorpt_correction_T_max  0.801
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_type   'gaussian, SHELX76 (Sheldrick, 1976)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_meas      1.189(5)
_exptl_crystal_density_method    flotation
_exptl_crystal_description       lathe-shaped
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.26
_refine_ls_abs_structure_Flack   0
_refine_ls_extinction_coef       1.3E-6(1)
_refine_ls_extinction_method     SHELX76
_refine_ls_goodness_of_fit_obs   3.79
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     219
_refine_ls_number_reflns         1728
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.070
_refine_ls_shift/esd_max         0.002
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(F) + 0.000045F^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.075
_reflns_number_observed          1728
_reflns_number_total             2134
_reflns_observed_criterion       F>6.0\sF
_cod_data_source_file            hr1005.cif
_cod_data_source_block           TOZ
_cod_depositor_comments
;
 Adding the _atom_site_type_symbol data item.

 Antanas Vaitkus,
 2017-01-17

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/[\s^2^(F) + 0.000045F^2^]' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w = 1/[\s^2^(F) +
0.000045F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1529.0(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C13 H23 N1 O5'
_cod_database_code               2010185
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.119(4) 0.076(4) 0.061(3) -0.006(3) 0.028(3) 0.002(3)
C2 0.087(4) 0.074(4) 0.066(3) -0.009(3) 0.013(3) 0.010(3)
C3 0.055(2) 0.044(3) 0.066(3) 0.000(2) 0.028(2) 0.008(2)
C4 0.056(2) 0.044(2) 0.062(3) 0.002(2) 0.023(2) -0.002(2)
C5 0.061(3) 0.070(3) 0.087(4) 0.003(2) 0.041(3) 0.003(3)
C6 0.126(5) 0.097(5) 0.083(4) 0.011(4) 0.066(4) 0.008(3)
C1' 0.102(4) 0.075(4) 0.108(4) -0.023(4) 0.040(4) 0.010(3)
O1' 0.128(4) 0.113(4) 0.275(6) -0.015(3) 0.020(4) 0.075(4)
O2' 0.119(3) 0.107(3) 0.166(4) -0.016(3) -0.024(3) 0.038(3)
C2' 0.153(6) 0.078(4) 0.163(6) 0.003(4) -0.011(5) 0.037(4)
O4 0.062(2) 0.054(2) 0.070(2) -0.002(2) 0.011(2) -0.004(2)
N3 0.057(2) 0.043(2) 0.079(2) 0.007(2) 0.035(2) 0.018(2)
C7' 0.048(2) 0.052(2) 0.068(3) 0.004(2) 0.021(2) 0.009(2)
O7' 0.063(2) 0.050(2) 0.095(2) 0.0060(10) 0.034(2) 0.016(2)
O8' 0.060(2) 0.057(2) 0.090(2) 0.0050(10) 0.041(2) 0.018(2)
C9' 0.053(2) 0.072(3) 0.087(3) 0.001(2) 0.037(2) 0.007(3)
C10 0.053(3) 0.152(5) 0.120(4) 0.021(3) 0.025(3) 0.038(4)
C11' 0.136(5) 0.124(5) 0.116(5) -0.030(4) 0.074(4) -0.033(4)
C12 0.076(3) 0.100(4) 0.114(4) 0.000(3) 0.052(3) 0.036(3)
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C1 C 0.3059(4) -0.0170(8) 0.5034(3)
C2 C 0.3630(4) 0.0489(9) 0.4356(3)
C3 C 0.3186(3) -0.0193(6) 0.3494(2)
C4 C 0.2151(3) 0.0474(6) 0.3305(2)
C5 C 0.1604(3) -0.0413(8) 0.3931(3)
C6 C 0.2005(5) 0.0308(10) 0.4784(3)
C1' C 0.3228(5) -0.2366(8) 0.5275(4)
O1' O 0.2652(3) -0.3616(7) 0.5267(4)
O2' O 0.4104(3) -0.2748(6) 0.5565(3)
C2' C 0.4352(4) -0.4687(8) 0.5953(4)
O4 O 0.1748(2) -0.0127(5) 0.2491(2)
N3 N 0.3733(2) 0.0620(5) 0.2903(2)
C7' C 0.4465(2) -0.0354(6) 0.2673(2)
O7' O 0.4679(2) -0.2113(4) 0.2827(2)
O8' O 0.4937(2) 0.0905(4) 0.2232(2)
C9' C 0.5734(3) 0.0200(6) 0.1842(3)
C10' C 0.6544(3) -0.0529(9) 0.2491(3)
C11' C 0.5398(4) -0.1411(9) 0.1222(3)
C12' C 0.6011(3) 0.2108(7) 0.1419(3)
H2'a H 0.5113 -0.4752 0.6160
H2'b H 0.3986 -0.4865 0.6471
H2'c H 0.4143 -0.5891 0.5518
H10'a H 0.7127 -0.1046 0.2200
H10'b H 0.6784 -0.0702 0.2904
H10'c H 0.6297 -0.1764 0.2830
H11'a H 0.5989 -0.1918 0.0938
H11'b H 0.5116 -0.2676 0.1521
H11'c H 0.4846 -0.0799 0.0758
H12'a H 0.6601 0.1775 0.1105
H12'b H 0.5401 0.2627 0.0982
H12'c H 0.6219 0.3276 0.1872
H1 H 0.328(3) 0.079(7) 0.553(3)
H2a H 0.427(3) 0.015(7) 0.444(3)
H2b H 0.366(3) 0.202(7) 0.433(3)
H3 H 0.320(2) -0.156(5) 0.346(2)
H4 H 0.213(2) 0.200(5) 0.334(2)
H5a H 0.163(2) -0.190(6) 0.393(2)
H5b H 0.091(3) -0.003(6) 0.374(2)
H6a H 0.165(3) -0.033(7) 0.513(3)
H6b H 0.197(3) 0.198(8) 0.479(3)
HO4 H 0.133(3) 0.060(6) 0.231(3)
HN3 H 0.364(2) 0.188(5) 0.278(2)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .017 .009 International_Tables_Vol_IV
H 0 0 International_Tables_Vol_IV
N .029 .018 International_Tables_Vol_IV
O .0471 .032 International_Tables_Vol_IV
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 1 -4
4 1 -2
-1 -2 -3
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
C2 C1 C6 110.8(4) yes
C2 C1 C1' 112.3(4) yes
C6 C1 C1' 112.2(4) yes
C1 C2 C3 114.0(4) yes
C2 C3 C4 110.1(3) yes
C2 C3 N3 109.6(3) yes
C4 C3 N3 111.3(3) yes
C3 C4 C5 109.7(3) yes
C3 C4 O4 109.7(3) yes
C5 C4 O4 111.5(3) yes
C4 C5 C6 111.2(4) yes
C1 C6 C5 113.1(4) yes
C1 C1' O1' 126.6(5) yes
C1 C1' O2' 112.9(4) yes
O1' C1' O2' 120.3(4) yes
C1' O2' C2' 119.3(4) yes
C3 N3 C7' 123.1(3) yes
N3 C7' O7' 125.5(2) yes
N3 C7' O8' 109.8(2) yes
O7' C7' O8' 124.7(2) yes
C7' O8' C9' 122.0(3) yes
O8' C9' C10' 109.9(3) yes
O8' C9' C11' 110.1(3) yes
O8' C9' C12' 102.5(3) yes
C10' C9' C11' 112.2(3) yes
C10' C9' C12' 111.3(3) yes
C11' C9' C12' 110.4(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.551(8) yes
C1 C6 1.520(9) yes
C1 C1' 1.510(7) yes
C2 C3 1.529(6) yes
C3 C4 1.518(6) yes
C3 N3 1.449(5) yes
C4 C5 1.512(6) yes
C4 O4 1.430(5) yes
C5 C6 1.509(7) yes
C1' O1' 1.160(8) yes
C1' O2' 1.283(8) yes
O2' C2' 1.448(7) yes
N3 C7' 1.331(5) yes
C7' O7' 1.215(5) yes
C7' O8' 1.354(5) yes
O8' C9' 1.469(6) yes
C9' C10' 1.517(6) yes
C9' C11' 1.499(7) yes
C9' C12' 1.523(6) yes
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
C1 C6 C5 C4 -56.7(6) yes
C6 C5 C4 C3 60.9(5) yes
C5 C4 C3 C2 -58.5(4) yes
C4 C3 C2 C1 53.1(5) yes
C3 C2 C1 C6 -47.7(6) yes
C2 C1 C6 C5 48.9(6) yes
C6 C1 C1' O1' 1.4(9) yes
C1 C1' O2' C2' 169.4(5) yes
O4 C4 C3 N3 56.8(4) yes
C4 C3 N3 C7' -147.7(3) yes
C2 C3 N3 C7' 90.2(4) yes
C3 N3 C7' O8' -169.3(3) yes
N3 C7' O8' C9' -175.2(3) yes
C7' O8' C9' C12' 179.2(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139057376
