#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/03/2200385.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_2200385
loop_
_publ_author_name
'Pavkovic, Stephen F.'
'Zerkowski, Jonathan A.'
'Zeng, Qi'
_publ_section_title
;
 Cyclo(alanine-4-hydroxyproline)
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o798
_journal_page_last               o799
_journal_paper_doi               10.1107/S1600536801012636
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C8 H12 N2 O3'
_chemical_formula_moiety         'C8 H12 N2 O3'
_chemical_formula_sum            'C8 H12 N2 O3'
_chemical_formula_weight         184.20
_chemical_name_common            cyclo(analine-4-hydroxyproline)
_chemical_name_systematic
;
2-hydroxy-6-methyl-1,2,3,5,6,7,8,8a-octahydro-7-azaindolizine-5,8-dione
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 103.719(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.626(2)
_cell_length_b                   9.924(3)
_cell_length_c                   5.1790(10)
_cell_measurement_reflns_used    16
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      11
_cell_volume                     430.70(18)
_computing_cell_refinement       'Please provide'
_computing_data_collection       'Please provide'
_computing_data_reduction        'Please provide'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      21(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'MAKER? four-circle'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  none
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71070
_diffrn_reflns_av_R_equivalents  .0353
_diffrn_reflns_av_sigmaI/netI    .0738
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2100
_diffrn_reflns_theta_full        28.01
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         2.43
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .110
_exptl_absorpt_correction_T_max  .978
_exptl_absorpt_correction_T_min  .952
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             196
_exptl_crystal_size_max          .45
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .20
_refine_diff_density_max         .199
_refine_diff_density_min         -.175
_refine_ls_extinction_coef       .074(13)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   .989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1099
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      .989
_refine_ls_R_factor_all          .0562
_refine_ls_R_factor_gt           .0400
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0264P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0960
_reflns_number_gt                835
_reflns_number_total             1099
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6054.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2200385
_cod_database_fobs_code          2200385
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 .2467(3) .6102(3) .3226(5) .0347(6) Uani d . 1 . . C
C2 -.0077(3) .4887(3) .2753(5) .0342(6) Uani d . 1 . . C
H2 -.0731 .5261 .1098 .041 Uiso calc R 1 . . H
C3 .0726(3) .3612(3) .2082(5) .0325(6) Uani d . 1 . . C
C4 .2801(3) .5138(3) .1155(5) .0325(6) Uani d . 1 . . C
H4 .2393 .5525 -.0617 .039 Uiso calc R 1 . . H
C5 .4557(4) .4786(3) .1508(6) .0408(7) Uani d . 1 . . C
H5A .5094 .4739 .3377 .049 Uiso calc R 1 . . H
H5B .5092 .5449 .0648 .049 Uiso calc R 1 . . H
C6 .4536(3) .3413(3) .0187(6) .0390(7) Uani d . 1 . . C
H6 .5517 .2911 .0942 .047 Uiso calc R 1 . . H
C7 .3088(4) .2714(3) .0811(7) .0444(7) Uani d . 1 . . C
H7A .2542 .2162 -.0674 .053 Uiso calc R 1 . . H
H7B .3406 .2149 .2375 .053 Uiso calc R 1 . . H
C8 -.1152(4) .4593(3) .4595(8) .0524(8) Uani d . 1 . . C
H8A -.1638 .5415 .4984 .079 Uiso calc R 1 . . H
H8B -.0534 .4209 .6216 .079 Uiso calc R 1 . . H
H8C -.1966 .3969 .3758 .079 Uiso calc R 1 . . H
N1 .1110(3) .5890(2) .3947(4) .0350(5) Uani d . 1 . . N
H1 .0918 .6379 .5206 .042 Uiso calc R 1 . . H
N2 .2062(3) .3816(2) .1281(4) .0342(5) Uani d . 1 . . N
O1 .3407(3) .7007(2) .4120(4) .0514(6) Uani d . 1 . . O
O2 .0168(2) .24882(19) .2236(4) .0466(6) Uani d . 1 . . O
O3 .4307(3) .3558(3) -.2594(4) .0625(7) Uani d . 1 . . O
H3 .4828 .2984 -.3154 .075 Uiso calc R 1 . . H
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 .0388(15) .0284(13) .0396(15) .0003(11) .0148(11) .0010(11)
C2 .0323(14) .0318(14) .0383(14) .0023(11) .0076(11) -.0003(11)
C3 .0348(14) .0324(14) .0303(13) -.0034(11) .0076(10) -.0002(11)
C4 .0400(14) .0284(12) .0324(13) .0000(11) .0149(11) .0017(11)
C5 .0385(15) .0388(15) .0511(16) -.0005(12) .0225(13) .0014(13)
C6 .0381(15) .0413(16) .0395(15) .0094(12) .0130(12) .0044(12)
C7 .0502(16) .0330(15) .0531(19) .0011(13) .0188(14) -.0092(13)
C8 .0410(16) .0476(17) .077(2) -.0074(14) .0311(16) -.0152(17)
N1 .0391(13) .0283(12) .0417(13) -.0034(10) .0179(10) -.0077(9)
N2 .0375(12) .0265(11) .0412(13) -.0003(10) .0142(9) -.0061(10)
O1 .0528(13) .0426(12) .0674(16) -.0181(10) .0313(11) -.0189(11)
O2 .0511(12) .0339(11) .0607(15) -.0104(9) .0249(11) -.0040(9)
O3 .0801(17) .0728(17) .0421(12) .0356(13) .0295(11) .0071(11)
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 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
O1 C1 N1 124.0(2) no
O1 C1 C4 120.7(3) no
N1 C1 C4 115.3(2) no
N1 C2 C8 109.8(2) no
N1 C2 C3 110.7(2) no
C8 C2 C3 111.4(2) no
N1 C2 H2 108.3 no
C8 C2 H2 108.3 no
C3 C2 H2 108.3 no
O2 C3 N2 122.9(3) no
O2 C3 C2 122.3(2) no
N2 C3 C2 114.8(2) no
N2 C4 C1 112.1(2) no
N2 C4 C5 102.7(2) no
C1 C4 C5 114.2(2) no
N2 C4 H4 109.2 no
C1 C4 H4 109.2 no
C5 C4 H4 109.2 no
C4 C5 C6 104.2(2) no
C4 C5 H5A 110.9 no
C6 C5 H5A 110.9 no
C4 C5 H5B 110.9 no
C6 C5 H5B 110.9 no
H5A C5 H5B 108.9 no
O3 C6 C5 110.5(2) no
O3 C6 C7 109.7(2) no
C5 C6 C7 103.5(2) no
O3 C6 H6 110.9 no
C5 C6 H6 110.9 no
C7 C6 H6 110.9 no
N2 C7 C6 104.7(2) no
N2 C7 H7A 110.8 no
C6 C7 H7A 110.8 no
N2 C7 H7B 110.8 no
C6 C7 H7B 110.8 no
H7A C7 H7B 108.9 no
C2 C8 H8A 109.5 no
C2 C8 H8B 109.5 no
H8A C8 H8B 109.5 no
C2 C8 H8C 109.5 no
H8A C8 H8C 109.5 no
H8B C8 H8C 109.5 no
C1 N1 C2 124.5(2) no
C1 N1 H1 117.7 no
C2 N1 H1 117.7 no
C3 N2 C4 124.6(2) no
C3 N2 C7 122.7(2) no
C4 N2 C7 112.0(2) no
C6 O3 H3 109.5 no
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 O1 . 1.225(3) no
C1 N1 . 1.327(3) no
C1 C4 . 1.515(3) no
C2 N1 . 1.456(3) no
C2 C8 . 1.508(4) no
C2 C3 . 1.522(4) no
C2 H2 . .9800 no
C3 O2 . 1.225(3) no
C3 N2 . 1.330(3) no
C4 N2 . 1.467(3) no
C4 C5 . 1.523(4) no
C4 H4 . .9800 no
C5 C6 . 1.523(4) no
C5 H5A . .9700 no
C5 H5B . .9700 no
C6 O3 . 1.414(4) no
C6 C7 . 1.529(4) no
C6 H6 . .9800 no
C7 N2 . 1.463(4) no
C7 H7A . .9700 no
C7 H7B . .9700 no
C8 H8A . .9600 no
C8 H8B . .9600 no
C8 H8C . .9600 no
N1 H1 . .8600 no
O3 H3 . .8200 no
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
N1 H1 O2 2_556 .86 2.10 2.945(3) 165.2 yes
O3 H3 O1 2_645 .82 1.97 2.761(3) 162.7 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
N1 C2 C3 O2 145.8(3) no
C8 C2 C3 O2 23.3(4) no
N1 C2 C3 N2 -35.2(3) no
C8 C2 C3 N2 -157.7(2) no
O1 C1 C4 N2 151.9(3) no
N1 C1 C4 N2 -28.5(3) no
O1 C1 C4 C5 35.6(4) no
N1 C1 C4 C5 -144.7(2) no
N2 C4 C5 C6 33.0(3) no
C1 C4 C5 C6 154.5(2) no
C4 C5 C6 O3 82.0(3) no
C4 C5 C6 C7 -35.5(3) no
O3 C6 C7 N2 -94.0(3) no
C5 C6 C7 N2 23.9(3) no
O1 C1 N1 C2 174.9(3) no
C4 C1 N1 C2 -4.7(4) no
C8 C2 N1 C1 160.8(2) no
C3 C2 N1 C1 37.4(3) no
O2 C3 N2 C4 -177.8(3) no
C2 C3 N2 C4 3.2(4) no
O2 C3 N2 C7 -7.4(4) no
C2 C3 N2 C7 173.6(2) no
C1 C4 N2 C3 29.7(4) no
C5 C4 N2 C3 152.7(2) no
C1 C4 N2 C7 -141.6(3) no
C5 C4 N2 C7 -18.5(3) no
C6 C7 N2 C3 -174.9(2) no
C6 C7 N2 C4 -3.4(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24215522
