#------------------------------------------------------------------------------
#$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $
#$Revision: 134621 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/60/2006022.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_2006022
loop_
_publ_author_name
'Burkett, B. A.'
'Chai, C. L. L.'
'Hockless, D. C. R.'
_publ_contact_author
;
Dr. David C. R. Hockless
Research School of Chemistry
Institute of Advanced Studies
Australian National University
Canberra
ACT 0200
Australia
;
_publ_section_title
1-Acetyl-4-[(1<i>R</i>,2<i>S</i>,5<i>R</i>)-3-menthyloxycarbonyl]piperazine-2,5-dione
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              327
_journal_page_last               329
_journal_paper_doi               10.1107/S0108270196013753
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C17 H26 N2 O5'
_chemical_formula_sum            'C17 H26 N2 O5'
_chemical_formula_weight         338.40
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           'by teXsan v1.7'
_cell_angle_alpha                90
_cell_angle_beta                 96.26(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.977(4)
_cell_length_b                   5.757(4)
_cell_length_c                   16.047(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      20.9
_cell_volume                     916.2(8)
_computing_cell_refinement
;
MSC/AFC Diffractometer Control Software
;
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992)
;
_computing_data_reduction
;
TEXSAN
(Molecular Structure Corporation, 1992)
;
_computing_publication_material
;
TEXSAN
;
_computing_structure_refinement
;
TEXSAN
;
_computing_structure_solution
;
SIR92 (Altomare et al., 1994), DIRDIF92 (Beurskens et al., 1992)
;
_diffrn_ambient_temperature      296.0(10)
_diffrn_measurement_device       'Rigaku AFC6R'
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_radiation_monochromator  'equatorial graphite'
_diffrn_radiation_source         'Rigaku RU200B rotating Cu anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            1622
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         60.02
_diffrn_reflns_theta_min         2.77
_diffrn_standards_decay_%        negligible
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type
;
empirical based on azimuthal (\y) scans (North, Phillips & Mathews, 1968)
;
_exptl_absorpt_process_details
;
based on azimuthal (\Y) scans (North, Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             364.00
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.27
_refine_ls_extinction_coef       '1.3 (7) \\times 10^-^^6^'
_refine_ls_extinction_method     Zachariasen_type-2_Gaussian_isotropic
_refine_ls_goodness_of_fit_all   1.989
_refine_ls_goodness_of_fit_obs   1.989
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1521
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_obs          0.0983
_refine_ls_shift/esd_max         0.0188
_refine_ls_shift/esd_mean        0.0055
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=4F~o~^2^/[\s^2^(F~o~^2^)+(0.007F~o~^2^)^2^]
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0448
_refine_ls_wR_factor_obs         0.0448
_reflns_number_observed          1521
_reflns_number_total             1525
_reflns_observed_criterion       I>0
_[local]_cod_data_source_file    ta1117.cif
_[local]_cod_data_source_block   BXB1-Alldata
_[local]_cod_cif_authors_sg_H-M  'P 21 '
_[local]_cod_chemical_formula_sum_orig 'C17 H26 N2 O5 '
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '
w=4F~o~^2^/[\s^2^(F~o~^2^)+(0.007F~o~^2^)^2^]' was changed to 'calc'.
New tag '_refine_ls_weighting_details' was created. The value of the
new tag was set to 'w=4F~o~^2^/[\s^2^(F~o~^2^)+(0.007F~o~^2^)^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2006022
loop_
_symmetry_equiv_pos_as_xyz
' +x, +y, +z'
' -x,1/2+y, -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_22
_atom_site_aniso_U_23
_atom_site_aniso_U_33
O(2) 0.112(3) 0.051(4) 0.045(3) 0.074(4) 0.028(3) 0.111(4)
O(5) 0.073(3) 0.015(3) 0.000(2) 0.041(3) 0.000(3) 0.082(3)
O(7) 0.160(5) 0.073(5) 0.050(3) 0.178(8) 0.038(5) 0.080(3)
O(9) 0.115(4) 0.004(3) 0.026(3) 0.039(3) -0.006(3) 0.080(3)
O(10) 0.104(3) 0.005(3) 0.023(2) 0.044(3) 0.008(2) 0.056(2)
N(1) 0.052(3) 0.014(3) 0.002(2) 0.057(4) -0.002(3) 0.056(3)
N(4) 0.052(3) 0.004(3) 0.007(2) 0.042(3) 0.005(3) 0.051(3)
C(1') 0.090(4) 0.001(4) 0.016(3) 0.052(5) 0.003(4) 0.054(3)
C(2) 0.053(4) 0.009(3) 0.003(3) 0.055(5) 0.008(4) 0.069(4)
C(2') 0.117(6) 0.006(5) 0.012(4) 0.063(5) 0.006(4) 0.065(4)
C(3) 0.074(4) 0.006(3) 0.014(3) 0.037(4) 0.004(4) 0.060(4)
C(3') 0.180(7) 0.029(7) 0.016(5) 0.100(7) 0.012(5) 0.060(4)
C(4') 0.166(8) -0.015(8) 0.049(5) 0.109(8) -0.006(6) 0.076(5)
C(5) 0.046(3) -0.003(3) -0.002(3) 0.046(4) -0.003(4) 0.057(4)
C(5') 0.092(5) -0.008(5) 0.015(3) 0.093(7) -0.013(4) 0.052(4)
C(6) 0.069(4) 0.012(4) 0.009(3) 0.057(5) 0.007(4) 0.058(3)
C(6') 0.087(4) -0.006(4) 0.010(3) 0.089(6) -0.005(4) 0.053(3)
C(7') 0.106(7) 0.051(8) -0.027(6) 0.15(1) -0.037(9) 0.166(8)
C(7) 0.072(4) 0.032(5) 0.015(4) 0.133(9) -0.003(5) 0.062(4)
C(8') 0.12(1) 0.04(1) 0.03(1) 0.22(2) -0.17(2) 0.62(3)
C(8) 0.085(5) 0.028(5) 0.024(4) 0.113(7) -0.008(5) 0.078(4)
C(9') 0.128(8) 0.011(9) -0.065(8) 0.22(2) -0.12(1) 0.28(1)
C(9) 0.052(4) -0.004(4) 0.003(3) 0.058(5) -0.005(4) 0.067(4)
C(10') 0.100(5) -0.018(7) 0.023(4) 0.23(1) -0.036(7) 0.089(5)
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
O(2) 1.000 0.6018(4) 0.5478 0.5000(3) 0.097(2) Uani d
O(5) 1.000 0.9147(3) -0.200(1) 0.5044(2) 0.066(1) Uani d
O(7) 1.000 0.6633(5) 0.128(2) 0.7036(3) 0.137(3) Uani d
O(9) 1.000 0.8738(5) -0.170(1) 0.3348(3) 0.077(2) Uani d
O(10) 1.000 0.8545(4) 0.209(1) 0.3014(2) 0.067(1) Uani d
N(1) 1.000 0.7015(4) 0.245(1) 0.5756(3) 0.055(2) Uani d
N(4) 1.000 0.8104(4) 0.098(1) 0.4288(3) 0.048(1) Uani d
C(1') 1.000 0.8973(6) 0.170(1) 0.2173(3) 0.065(2) Uani d
C(2) 1.000 0.6790(6) 0.386(2) 0.5064(4) 0.059(2) Uani d
C(2') 1.000 0.8370(7) 0.369(2) 0.1656(3) 0.082(2) Uani d
C(3) 1.000 0.7646(5) 0.342(1) 0.4358(3) 0.056(2) Uani d
C(3') 1.000 0.8998(8) 0.370(2) 0.0811(4) 0.113(3) Uani d
C(4') 1.000 1.0512(9) 0.365(2) 0.0930(4) 0.114(3) Uani d
C(5) 1.000 0.8514(5) -0.018(1) 0.5013(4) 0.050(2) Uani d
C(5') 1.000 1.1036(7) 0.153(2) 0.1414(4) 0.079(2) Uani d
C(6) 1.000 0.8133(5) 0.084(1) 0.5812(3) 0.061(2) Uani d
C(6') 1.000 1.0483(6) 0.159(2) 0.2268(3) 0.076(2) Uani d
C(7) 1.000 0.6283(6) 0.250(2) 0.6465(4) 0.088(3) Uani d
C(7') 1.000 0.6812(9) 0.371(2) 0.1536(6) 0.144(4) Uani d
C(8) 1.000 0.5165(6) 0.423(2) 0.6482(4) 0.091(3) Uani d
C(8') 1.000 0.621(1) 0.574(3) 0.148(1) 0.32(1) Uani d
C(9) 1.000 0.8509(5) 0.031(2) 0.3512(4) 0.059(2) Uani d
C(9') 1.000 0.622(1) 0.192(3) 0.0951(9) 0.217(6) Uani d
C(10') 1.000 1.2554(7) 0.136(2) 0.1507(4) 0.140(4) Uani d
H(1') 1.000 0.8611 0.0271 0.1951 0.078 Uiso c
H(2') 1.000 0.8652 0.5078 0.1944 0.098 Uiso c
H(3a) 1.000 0.7134 0.3831 0.3846 0.068 Uiso c
H(3b) 1.000 0.8422 0.4383 0.4444 0.068 Uiso c
H(3'a) 1.000 0.8716 0.5070 0.0511 0.136 Uiso c
H(3'b) 1.000 0.8683 0.2376 0.0496 0.136 Uiso c
H(4'a) 1.000 1.0837 0.3630 0.0395 0.137 Uiso c
H(4'b) 1.000 1.0831 0.4999 0.1227 0.137 Uiso c
H(5') 1.000 1.0683 0.0196 0.1121 0.095 Uiso c
H(6a) 1.000 0.8902 0.1627 0.6075 0.073 Uiso c
H(6b) 1.000 0.7914 -0.0420 0.6157 0.073 Uiso c
H(6'a) 1.000 1.0766 0.0229 0.2572 0.091 Uiso c
H(6'b) 1.000 1.0829 0.2921 0.2569 0.091 Uiso c
H(7') 1.000 0.6591 0.3156 0.2062 0.173 Uiso c
H(8'a) 1.000 0.6045 0.6241 0.2023 0.384 Uiso c
H(8'b) 1.000 0.5382 0.5606 0.1132 0.384 Uiso c
H(8'c) 1.000 0.6774 0.6832 0.1244 0.384 Uiso c
H(8a) 1.000 0.4776 0.4087 0.6994 0.109 Uiso c
H(8b) 1.000 0.4497 0.3952 0.6025 0.109 Uiso c
H(8c) 1.000 0.5516 0.5757 0.6439 0.109 Uiso c
H(9'a) 1.000 0.6506 0.0426 0.1154 0.261 Uiso c
H(9'b) 1.000 0.5268 0.2010 0.0908 0.261 Uiso c
H(9'c) 1.000 0.6519 0.2160 0.0414 0.261 Uiso c
H(10'a) 1.000 1.2818 -0.0173 0.1667 0.168 Uiso c
H(10'b) 1.000 1.2921 0.2424 0.1925 0.168 Uiso c
H(10'c) 1.000 1.2878 0.1730 0.0988 0.168 Uiso c
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.018 0.009
;
International Tables for Crystallography
(Vol. C)
;
H 0.000 0.000
;
International Tables for Crystallography
(Vol. C)
;
N 0.031 0.018
;
International Tables for Crystallography
(Vol. C)
;
O 0.049 0.032
;
International Tables for Crystallography
(Vol. C)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 0 0
1 1 1
0 1 2
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
C(1') O(10) C(9) 117.9(7) no
C(2) N(1) C(6) 119.4(6) yes
C(2) N(1) C(7) 125.6(7) no
C(6) N(1) C(7) 114.9(6) no
C(3) N(4) C(5) 117.2(7) yes
C(3) N(4) C(9) 116.7(6) no
C(5) N(4) C(9) 122.5(7) no
O(10) C(1') C(2') 104.3(6) no
O(10) C(1') C(6') 107.5(6) no
O(10) C(1') H(1') 109.9 no
C(2') C(1') C(6') 115.0(7) no
C(2') C(1') H(1') 110.0 no
C(6') C(1') H(1') 109.9 no
O(2) C(2) N(1) 125.2(8) no
O(2) C(2) C(3) 118.4(8) no
N(1) C(2) C(3) 116.4(7) yes
C(1') C(2') C(3') 108.1(8) no
C(1') C(2') C(7') 114.1(9) no
C(1') C(2') H(2') 107.1 no
C(3') C(2') C(7') 112.8(8) no
C(3') C(2') H(2') 107.2 no
C(7') C(2') H(2') 107.2 no
N(4) C(3) C(2) 115.0(7) yes
N(4) C(3) H(3a) 108.0 no
N(4) C(3) H(3b) 108.0 no
C(2) C(3) H(3a) 108.1 no
C(2) C(3) H(3b) 108.1 no
H(3a) C(3) H(3b) 109.6 no
C(2') C(3') C(4') 112.6(7) no
C(2') C(3') H(3'a) 108.7 no
C(2') C(3') H(3'b) 108.6 no
C(4') C(3') H(3'a) 108.8 no
C(4') C(3') H(3'b) 108.7 no
H(3'a) C(3') H(3'b) 109.5 no
C(3') C(4') C(5') 111.7(9) no
C(3') C(4') H(4'a) 108.9 no
C(3') C(4') H(4'b) 109.0 no
C(5') C(4') H(4'a) 108.8 no
C(5') C(4') H(4'b) 108.8 no
H(4'a) C(4') H(4'b) 109.6 no
O(5) C(5) N(4) 123.5(8) no
O(5) C(5) C(6) 118.7(7) no
N(4) C(5) C(6) 117.7(8) yes
C(4') C(5') C(6') 107.8(8) no
C(4') C(5') C(10') 113.0(10) no
C(4') C(5') H(5') 108.2 no
C(6') C(5') C(10') 111.6(7) no
C(6') C(5') H(5') 108.1 no
C(10') C(5') H(5') 108.1 no
N(1) C(6) C(5) 117.4(6) yes
N(1) C(6) H(6b) 107.5 no
N(1) C(6) H(6a) 107.6 no
C(5) C(6) H(6b) 107.4 no
C(5) C(6) H(6a) 107.4 no
H(6b) C(6) H(6a) 109.4 no
C(1') C(6') C(5') 111.4(6) no
C(1') C(6') H(6'a) 109.0 no
C(1') C(6') H(6'b) 109.0 no
C(5') C(6') H(6'a) 108.9 no
C(5') C(6') H(6'b) 109.0 no
H(6'a) C(6') H(6'b) 109.4 no
C(2') C(7') C(8') 118(2) no
C(2') C(7') C(9') 114.0(10) no
C(2') C(7') H(7') 102.3 no
C(8') C(7') C(9') 115.0(10) no
C(8') C(7') H(7') 102.7 no
C(9') C(7') H(7') 102.2 no
O(7) C(7) N(1) 118.8(9) no
O(7) C(7) C(8) 122.6(9) no
N(1) C(7) C(8) 118.5(9) no
C(7') C(8') H(8'b) 109.1 no
C(7') C(8') H(8'c) 109.3 no
C(7') C(8') H(8'a) 108.8 no
H(8'b) C(8') H(8'c) 110.1 no
H(8'b) C(8') H(8'a) 109.6 no
H(8'c) C(8') H(8'a) 109.9 no
C(7) C(8) H(8b) 109.4 no
C(7) C(8) H(8c) 109.4 no
C(7) C(8) H(8a) 109.4 no
H(8b) C(8) H(8c) 109.6 no
H(8b) C(8) H(8a) 109.5 no
H(8c) C(8) H(8a) 109.6 no
C(7') C(9') H(9'b) 109.5 no
C(7') C(9') H(9'c) 109.6 no
C(7') C(9') H(9'a) 109.5 no
H(9'b) C(9') H(9'c) 109.6 no
H(9'b) C(9') H(9'a) 109.3 no
H(9'c) C(9') H(9'a) 109.4 no
O(9) C(9) O(10) 126.8(8) no
O(9) C(9) N(4) 122.2(8) no
O(10) C(9) N(4) 110.9(7) no
C(5') C(10') H(10'b) 109.5 no
C(5') C(10') H(10'c) 109.5 no
C(5') C(10') H(10'a) 109.4 no
H(10'b) C(10') H(10'c) 109.7 no
H(10'b) C(10') H(10'a) 109.4 no
H(10'c) C(10') H(10'a) 109.4 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O(2) . C(2) . 1.204(9) yes
O(5) . C(5) . 1.229(9) yes
O(7) . C(7) . 1.18(1) no
O(9) . C(9) . 1.22(1) no
O(10) . C(1') . 1.478(7) yes
O(10) . C(9) . 1.304(9) no
N(1) . C(2) . 1.375(9) yes
N(1) . C(6) . 1.446(8) no
N(1) . C(7) . 1.418(9) yes
N(4) . C(3) . 1.484(9) no
N(4) . C(5) . 1.365(9) yes
N(4) . C(9) . 1.403(8) yes
C(1') . C(2') . 1.50(1) no
C(1') . C(6') . 1.500(9) no
C(1') . H(1') . 0.95 no
C(2) . C(3) . 1.515(9) no
C(2') . C(3') . 1.55(1) no
C(2') . C(7') . 1.55(1) no
C(2') . H(2') . 0.95 no
C(3) . H(3a) . 0.95 no
C(3) . H(3b) . 0.95 no
C(3') . C(4') . 1.50(1) no
C(3') . H(3'a) . 0.95 no
C(3') . H(3'b) . 0.95 no
C(4') . C(5') . 1.51(1) no
C(4') . H(4'a) . 0.95 no
C(4') . H(4'b) . 0.95 no
C(5) . C(6) . 1.492(9) no
C(5') . C(6') . 1.531(9) no
C(5') . C(10') . 1.51(1) no
C(5') . H(5') . 0.95 no
C(6) . H(6b) . 0.95 no
C(6) . H(6a) . 0.95 no
C(6') . H(6'a) . 0.95 no
C(6') . H(6'b) . 0.95 no
C(7') . C(8') . 1.31(2) no
C(7') . C(9') . 1.47(2) no
C(7') . H(7') . 0.95 no
C(7) . C(8) . 1.50(1) no
C(8') . H(8'b) . 0.95 no
C(8') . H(8'c) . 0.94 no
C(8') . H(8'a) . 0.95 no
C(8) . H(8b) . 0.95 no
C(8) . H(8c) . 0.95 no
C(8) . H(8a) . 0.95 no
C(9') . H(9'b) . 0.95 no
C(9') . H(9'c) . 0.95 no
C(9') . H(9'a) . 0.95 no
C(10') . H(10'b) . 0.95 no
C(10') . H(10'c) . 0.95 no
C(10') . H(10'a) . 0.95 no