#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/94/2009421.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_2009421
loop_
_publ_author_name
'Pohl, Ehmke'
'Sheldrick, George M.'
'Fischer, Stefan'
'Lackner, Helmut'
_publ_section_title
;Structure of
 cyclo-(<small>L</small>-threonyl-<small>D</small>-valyl-<small>L</small>-prolyl-sarcosyl-N-methyl-<small>L</small>-valyl-OThr)
 at 153 K
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              100
_journal_page_last               103
_journal_paper_doi               10.1107/S0108270193007334
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C24 H46 Cl N5 O8'
_chemical_formula_weight         568.11
_chemical_name_systematic
;
 cyclo(L-Thr-D-Val-L-Pro-Sar-N-MeVal-L-Val-OThr)
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.004(3)
_cell_length_b                   13.482(4)
_cell_length_c                   19.935(2)
_cell_measurement_reflns_used    56
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     2957.5(12)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1988a)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1988b)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  'SHELXL92 (Sheldrick, 1992)'
_computing_structure_refinement  'SHELXL92 (Sheldrick, 1992)'
_computing_structure_solution    'SHELXS90 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measurement_device       'Stoe-Siemens four-circle diffractometer'
_diffrn_measurement_method       'Profile data from 2θ/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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7076
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       Plates
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.80
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.231
_refine_ls_abs_structure_details 'Absolute configuration from Flack (1983)'
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.064
_refine_ls_goodness_of_fit_obs   1.065
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5193
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.083
_refine_ls_restrained_S_obs      1.070
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_obs          0.0334
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;calc w=1/[\s^2^(F~o~^2^) +(0.0482P)^2^ +0.8536P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         '0.0892 for all F^2^'
_reflns_number_observed          4852
_reflns_number_total             5195
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            sh1066.cif
_cod_data_source_block           penta
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2009421
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
Cl 0.86113(5) 0.38978(4) 0.51491(3) 0.03771(15) Uani d . 1 . Cl
O1S 0.1348(2) 0.09497(14) 0.58555(9) 0.0419(4) Uani d D 1 . O
H1SA 0.177(3) 0.076(2) 0.6208(14) 0.065(7) Uiso d D 1 . H
H1SB 0.186(3) 0.102(2) 0.5519(13) 0.065(7) Uiso d D 1 . H
O2M -0.0290(7) 0.2198(5) 0.6446(3) 0.0232(12) Uani d PDU 0.546(10) 1 O
H2M 0.011(4) 0.200(3) 0.6130(17) 0.028 Uiso d PD 0.546(10) 1 H
C2M 0.0060(9) 0.3213(7) 0.6404(5) 0.030(2) Uani d PDU 0.546(10) 1 C
H2MA 0.003(3) 0.3513(9) 0.6851(6) 0.045 Uiso calc PR 0.546(10) 1 H
H2MB -0.050(2) 0.3566(9) 0.6104(14) 0.045 Uiso calc PR 0.546(10) 1 H
H2MC 0.0889(14) 0.3259(7) 0.6228(15) 0.045 Uiso calc PR 0.546(10) 1 H
O2M' 0.0298(6) 0.3184(6) 0.6277(4) 0.0266(15) Uani d PDU 0.454(10) 2 O
H2M' -0.008(4) 0.339(3) 0.5938(17) 0.032 Uiso d PD 0.454(10) 2 H
C2M' -0.0228(13) 0.2213(8) 0.6279(6) 0.025(2) Uani d PDU 0.454(10) 2 C
H2MD 0.0407(14) 0.1719(9) 0.6193(19) 0.038 Uiso calc PR 0.454(10) 2 H
H2ME -0.085(3) 0.2171(12) 0.5928(13) 0.038 Uiso calc PR 0.454(10) 2 H
H2MF -0.060(3) 0.2084(13) 0.6716(8) 0.038 Uiso calc PR 0.454(10) 2 H
C1 0.5845(2) 0.10385(14) 0.64123(10) 0.0195(4) Uani d . 1 . C
O1 0.63537(12) 0.10834(10) 0.69555(6) 0.0241(3) Uani d . 1 . O
N1 0.7230(2) 0.23305(12) 0.60434(9) 0.0226(4) Uani d D 1 . N
H1A 0.6797(19) 0.2718(16) 0.6321(11) 0.034 Uiso d D 1 . H
H1B 0.7867(18) 0.2109(18) 0.6286(11) 0.034 Uiso d D 1 . H
H1C 0.756(2) 0.2676(16) 0.5701(10) 0.034 Uiso d D 1 . H
C1A 0.6391(2) 0.15466(14) 0.57998(10) 0.0214(4) Uani d . 1 . C
H1AA 0.5729(2) 0.18535(14) 0.55256(10) 0.026 Uiso calc R 1 . H
C1B 0.7073(2) 0.07790(15) 0.53787(10) 0.0230(4) Uani d . 1 . C
H1BB 0.6493(2) 0.02508(15) 0.52316(10) 0.028 Uiso calc R 1 . H
O1G1 0.79494(12) 0.03554(10) 0.58398(7) 0.0231(3) Uani d . 1 . O
C1G2 0.7713(2) 0.1204(2) 0.47687(11) 0.0343(5) Uani d . 1 . C
H1G1 0.7120(3) 0.1546(10) 0.4484(4) 0.051 Uiso calc R 1 . H
H1G2 0.8093(12) 0.0665(2) 0.4514(4) 0.051 Uiso calc R 1 . H
H1G3 0.8338(10) 0.1674(9) 0.49141(11) 0.051 Uiso calc R 1 . H
C2 0.3469(2) 0.02095(14) 0.72347(10) 0.0206(4) Uani d . 1 . C
O2 0.24634(12) 0.04766(11) 0.70199(7) 0.0270(3) Uani d . 1 . O
N2 0.48410(14) 0.05128(12) 0.62850(8) 0.0207(3) Uani d . 1 . N
H2 0.449(2) 0.0624(17) 0.5875(12) 0.025 Uiso d . 1 . H
C2A 0.4395(2) -0.02421(14) 0.67490(10) 0.0203(4) Uani d . 1 . C
H2A 0.5094(2) -0.05152(14) 0.70109(10) 0.024 Uiso calc R 1 . H
C2B 0.3773(2) -0.10925(14) 0.63630(10) 0.0259(4) Uani d . 1 . C
H2B 0.2976(2) -0.08452(14) 0.61900(10) 0.031 Uiso calc R 1 . H
C2G1 0.3526(2) -0.1946(2) 0.68483(13) 0.0379(5) Uani d . 1 . C
H2G1 0.3055(13) -0.1701(3) 0.7231(4) 0.057 Uiso calc R 1 . H
H2G2 0.4300(2) -0.2218(8) 0.7008(7) 0.057 Uiso calc R 1 . H
H2G3 0.3066(14) -0.2466(6) 0.6617(3) 0.057 Uiso calc R 1 . H
C2G2 0.4521(2) -0.1454(2) 0.57702(11) 0.0342(5) Uani d . 1 . C
H2G4 0.4563(13) -0.0930(5) 0.5430(4) 0.051 Uiso calc R 1 . H
H2G5 0.4137(8) -0.2044(7) 0.5577(5) 0.051 Uiso calc R 1 . H
H2G6 0.5343(5) -0.1619(12) 0.5922(2) 0.051 Uiso calc R 1 . H
C3 0.5267(2) -0.09341(14) 0.82455(9) 0.0218(4) Uani d . 1 . C
O3 0.44953(13) -0.15274(11) 0.84434(8) 0.0356(4) Uani d . 1 . O
N3 0.37391(15) 0.02887(12) 0.78820(8) 0.0240(4) Uani d D 1 . N
C3A 0.4946(2) 0.01583(14) 0.81899(10) 0.0222(4) Uani d D 1 . C
H3A 0.5582(2) 0.05292(14) 0.79343(10) 0.027 Uiso calc R 1 . H
C3B 0.4778(2) 0.0597(2) 0.89015(12) 0.0378(5) Uani d D 1 . C
H3BA 0.4692(2) 0.0062(2) 0.92382(12) 0.045 Uiso calc PR 0.684(12) 1 H
H3BB 0.5482(2) 0.1017(2) 0.90253(12) 0.045 Uiso calc PR 0.684(12) 1 H
H3BC 0.5174(2) 0.0167(2) 0.92394(12) 0.045 Uiso calc PR 0.316(12) 2 H
H3BD 0.5148(2) 0.1266(2) 0.89273(12) 0.045 Uiso calc PR 0.316(12) 2 H
C3G 0.3643(3) 0.1204(4) 0.8863(2) 0.0341(13) Uani d PD 0.684(12) 1 C
H3GA 0.3234(3) 0.1227(4) 0.9305(2) 0.041 Uiso calc PR 0.684(12) 1 H
H3GB 0.3832(3) 0.1891(4) 0.8721(2) 0.041 Uiso calc PR 0.684(12) 1 H
C3D 0.2860(2) 0.0711(2) 0.83619(11) 0.0332(5) Uani d D 1 . C
H3DA 0.2362(2) 0.0185(2) 0.85718(11) 0.040 Uiso calc PR 0.684(12) 1 H
H3DB 0.2316(2) 0.1195(2) 0.81392(11) 0.040 Uiso calc PR 0.684(12) 1 H
H3DC 0.2099(2) 0.0320(2) 0.83673(11) 0.040 Uiso calc PR 0.316(12) 2 H
H3DD 0.2666(2) 0.1407(2) 0.82456(11) 0.040 Uiso calc PR 0.316(12) 2 H
C3G' 0.3492(5) 0.0654(10) 0.9026(3) 0.034(3) Uani d PD 0.316(12) 2 C
H3GC 0.3303(5) 0.1250(10) 0.9297(3) 0.041 Uiso calc PR 0.316(12) 2 H
H3GD 0.3217(5) 0.0061(10) 0.9275(3) 0.041 Uiso calc PR 0.316(12) 2 H
C4 0.7737(2) -0.09325(13) 0.71500(9) 0.0190(4) Uani d . 1 . C
O4 0.70556(12) -0.14303(10) 0.68008(7) 0.0254(3) Uani d . 1 . O
C4A 0.7406(2) -0.06619(14) 0.78726(10) 0.0209(4) Uani d . 1 . C
H4A1 0.8117(2) -0.07758(14) 0.81675(10) 0.025 Uiso calc R 1 . H
H4A2 0.7191(2) 0.00501(14) 0.78969(10) 0.025 Uiso calc R 1 . H
N4 0.63886(14) -0.12558(11) 0.81047(8) 0.0208(3) Uani d . 1 . N
C4N 0.6636(2) -0.23183(14) 0.81806(11) 0.0294(5) Uani d . 1 . C
H4N1 0.7493(4) -0.2449(2) 0.8081(7) 0.044 Uiso calc R 1 . H
H4N2 0.6122(10) -0.2694(2) 0.7870(6) 0.044 Uiso calc R 1 . H
H4N3 0.6457(13) -0.2522(3) 0.8642(2) 0.044 Uiso calc R 1 . H
C5 0.8306(2) -0.05866(14) 0.57239(10) 0.0226(4) Uani d . 1 . C
O5 0.79912(14) -0.10574(11) 0.52464(7) 0.0318(3) Uani d . 1 . O
N5 0.88197(14) -0.06071(12) 0.69293(8) 0.0210(3) Uani d . 1 . N
C5A 0.9216(2) -0.09074(14) 0.62587(10) 0.0223(4) Uani d . 1 . C
H5A 0.9978(2) -0.05275(14) 0.61663(10) 0.027 Uiso calc R 1 . H
C5B 0.9553(2) -0.20151(15) 0.61866(11) 0.0279(4) Uani d . 1 . C
H5B 0.8806(2) -0.23901(15) 0.60544(11) 0.033 Uiso calc R 1 . H
C5G1 1.0487(2) -0.2118(2) 0.56275(11) 0.0340(5) Uani d . 1 . C
H5G1 1.0167(6) -0.1820(11) 0.5215(2) 0.051 Uiso calc R 1 . H
H5G2 1.0658(11) -0.2822(2) 0.5550(6) 0.051 Uiso calc R 1 . H
H5G3 1.1238(5) -0.1778(10) 0.5757(4) 0.051 Uiso calc R 1 . H
C5G2 1.0030(3) -0.2448(2) 0.68326(13) 0.0461(6) Uani d . 1 . C
H5G4 0.9376(5) -0.2469(13) 0.7166(3) 0.069 Uiso calc R 1 . H
H5G5 1.0696(12) -0.2035(8) 0.7001(5) 0.069 Uiso calc R 1 . H
H5G6 1.0330(16) -0.3122(6) 0.6751(2) 0.069 Uiso calc R 1 . H
C5N 0.9585(2) 0.0060(2) 0.73164(11) 0.0340(5) Uani d . 1 . C
H5N1 1.0349(7) 0.0172(10) 0.7076(4) 0.051 Uiso calc R 1 . H
H5N2 0.9757(13) -0.0237(6) 0.7755(3) 0.051 Uiso calc R 1 . H
H5N3 0.9164(7) 0.0694(5) 0.7379(7) 0.051 Uiso calc R 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8, 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8, 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8, 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8, 6.1.1.4'
Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8, 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
O1 C1 N2 125.0(2) y
O1 C1 C1A 120.5(2) y
N2 C1 C1A 114.3(2) y
N1 C1A C1 107.6(2) y
N1 C1A C1B 110.8(2) ?
C1 C1A C1B 109.2(2) ?
O1G1 C1B C1G2 110.4(2) ?
O1G1 C1B C1A 104.2(2) ?
C1G2 C1B C1A 114.3(2) ?
C5 O1G1 C1B 117.1(2) ?
O2 C2 N3 120.8(2) y
O2 C2 C2A 119.4(2) y
N3 C2 C2A 119.8(2) y
C1 N2 C2A 121.8(2) y
N2 C2A C2 110.31(15) y
N2 C2A C2B 110.6(2) ?
C2 C2A C2B 108.4(2) ?
C2G2 C2B C2G1 110.3(2) ?
C2G2 C2B C2A 112.7(2) ?
C2G1 C2B C2A 108.8(2) ?
O3 C3 N4 119.5(2) y
O3 C3 C3A 119.5(2) y
N4 C3 C3A 120.9(2) y
C2 N3 C3A 126.6(2) y
C2 N3 C3D 121.0(2) ?
C3A N3 C3D 111.5(2) ?
N3 C3A C3 110.9(2) y
N3 C3A C3B 103.2(2) ?
C3 C3A C3B 109.4(2) ?
C3G' C3B C3A 107.2(3) ?
C3G C3B C3A 105.2(2) ?
C3D C3G C3B 106.0(3) ?
N3 C3D C3G 103.3(2) ?
N3 C3D C3G' 104.4(3) ?
C3B C3G' C3D 107.9(4) ?
O4 C4 N5 122.4(2) y
O4 C4 C4A 121.4(2) y
N5 C4 C4A 116.2(2) y
N4 C4A C4 110.6(2) y
C3 N4 C4A 126.8(2) y
C3 N4 C4N 117.8(2) ?
C4A N4 C4N 115.4(2) ?
O5 C5 O1G1 123.5(2) y
O5 C5 C5A 126.6(2) y
O1G1 C5 C5A 109.8(2) y
C4 N5 C5N 122.8(2) ?
C4 N5 C5A 118.2(2) y
C5N N5 C5A 118.9(2) ?
N5 C5A C5 111.4(2) y
N5 C5A C5B 115.1(2) ?
C5 C5A C5B 111.5(2) ?
C5G2 C5B C5G1 110.8(2) ?
C5G2 C5B C5A 112.2(2) ?
C5G1 C5B C5A 108.5(2) ?
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
O2M C2M . 1.424(7) ?
O2M' C2M' . 1.432(8) ?
C1 O1 . 1.220(2) y
C1 N2 . 1.337(2) y
C1 C1A . 1.523(3) y
N1 C1A . 1.485(3) y
C1A C1B . 1.529(3) y
C1B O1G1 . 1.450(2) y
C1B C1G2 . 1.517(3) y
O1G1 C5 . 1.349(2) y
C2 O2 . 1.240(2) y
C2 N3 . 1.329(3) y
C2 C2A . 1.532(3) y
N2 C2A . 1.460(2) y
C2A C2B . 1.541(3) ?
C2B C2G2 . 1.520(3) ?
C2B C2G1 . 1.528(3) ?
C3 O3 . 1.232(2) y
C3 N4 . 1.338(3) y
C3 C3A . 1.519(3) y
N3 C3A . 1.474(3) y
N3 C3D . 1.475(3) ?
C3A C3B . 1.548(3) ?
C3B C3G' . 1.439(6) ?
C3B C3G . 1.495(4) ?
C3G C3D . 1.476(4) ?
C3D C3G' . 1.497(6) ?
C4 O4 . 1.224(2) y
C4 N5 . 1.343(2) y
C4 C4A . 1.530(3) y
C4A N4 . 1.452(2) y
N4 C4N . 1.466(2) ?
C5 O5 . 1.195(2) y
C5 C5A . 1.525(3) y
N5 C5N . 1.453(3) ?
N5 C5A . 1.463(2) y
C5A C5B . 1.546(3) ?
C5B C5G2 . 1.508(3) ?
C5B C5G1 . 1.523(3) ?
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 N2 C2A C2 92.6(2) y
C2 N3 C3A C3 -77.1(2) y
C3 N4 C4A C4 -112.2(2) y
C4 N5 C5A C5 58.2(2) y
N1 C1A C1 N2 162.5(2) y
N2 C2A C2 N3 -112.5(2) y
N3 C3A C3 N4 138.4(2) y
N4 C4A C4 N5 -165.4(2) y
C1A C1 N2 C2A 162.0(2) y
C2A C2 N3 C3A 12.4(3) y
C3A C3 N4 C4A -1.8(3) y
C4A C4 N5 C5A 175.7(2) y
