#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/45/4024568.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024568
loop_
_publ_author_name
'N. Deppermann'
'A. H. G. P. Prenzel'
'A. Beitat'
'W. Maison'
_publ_section_title
;
Synthesis of Proline-Based Diketopiperazine Scaffolds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4267
_journal_page_last               4271
_journal_paper_doi               10.1021/jo9004876
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_sum            'C17 H24 N2 O6'
_chemical_formula_weight         352.38
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1263(7)
_cell_length_b                   11.5380(10)
_cell_length_c                   16.9865(12)
_cell_measurement_temperature    193(2)
_cell_volume                     1788.7(2)
_computing_cell_refinement       'STOE IPDS Software (1997)'
_computing_data_collection       'STOE IPDS Software (1997)'
_computing_data_reduction        'STOE IPDS Software (1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'STOE IPDS'
_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  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16049
_diffrn_reflns_theta_full        28.05
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0570P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                3462
_reflns_number_total             4295
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9004876_si_002.cif
_cod_data_source_block           mais002w
_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 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               4024568
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.39166(18) -0.12393(13) 0.10078(9) 0.0324(3) Uani 1 1 d . . .
C2 C 0.54234(18) -0.15973(12) 0.07237(9) 0.0311(3) Uani 1 1 d . . .
H2 H 0.5270 -0.2257 0.0351 0.037 Uiso 1 1 calc R . .
C3 C 0.6548(2) -0.20064(16) 0.13211(10) 0.0395(4) Uani 1 1 d . . .
H3A H 0.664(2) -0.1445(19) 0.1749(13) 0.048(6) Uiso 1 1 d . . .
H3B H 0.627(2) -0.2751(19) 0.1560(12) 0.044(5) Uiso 1 1 d . . .
C4 C 0.7930(2) -0.20596(18) 0.08137(12) 0.0450(4) Uani 1 1 d . . .
H4A H 0.799(3) -0.277(2) 0.0535(16) 0.068(7) Uiso 1 1 d . . .
H4B H 0.883(3) -0.195(2) 0.1111(15) 0.061(7) Uiso 1 1 d . . .
C5 C 0.7782(2) -0.10549(16) 0.02237(12) 0.0408(4) Uani 1 1 d . . .
H5A H 0.829(3) -0.039(2) 0.0397(14) 0.057(6) Uiso 1 1 d . . .
H5B H 0.802(2) -0.1316(17) -0.0274(12) 0.036(5) Uiso 1 1 d . . .
C6 C 0.58228(18) 0.03872(13) 0.01437(9) 0.0322(3) Uani 1 1 d . . .
C7 C 0.43551(18) 0.07642(12) 0.04607(9) 0.0311(3) Uani 1 1 d . . .
H7 H 0.4526 0.1357 0.0880 0.037 Uiso 1 1 calc R . .
C8 C 0.3344(2) 0.12900(16) -0.01590(12) 0.0407(4) Uani 1 1 d . . .
H8A H 0.350(3) 0.206(2) -0.0210(14) 0.058(6) Uiso 1 1 d . . .
H8B H 0.353(3) 0.081(2) -0.0705(15) 0.056(6) Uiso 1 1 d . . .
C9 C 0.17688(17) 0.10575(12) 0.01513(9) 0.0307(3) Uani 1 1 d . . .
H9 H 0.1321 0.1790 0.0353 0.037 Uiso 1 1 calc R . .
C10 C 0.19345(18) 0.01608(13) 0.08286(9) 0.0307(3) Uani 1 1 d . . .
H10 H 0.136(2) -0.0479(18) 0.0737(12) 0.036(5) Uiso 1 1 d . . .
C11 C 0.15158(18) 0.07062(14) 0.16159(9) 0.0335(3) Uani 1 1 d . . .
C12 C -0.0703(2) 0.14386(14) 0.22839(9) 0.0345(3) Uani 1 1 d . . .
C13 C -0.0446(3) 0.08630(17) 0.30740(11) 0.0481(5) Uani 1 1 d . . .
H13A H 0.059(3) 0.088(2) 0.3234(14) 0.053(6) Uiso 1 1 d . . .
H13B H -0.093(3) 0.128(2) 0.3468(15) 0.061(7) Uiso 1 1 d . . .
H13C H -0.071(3) 0.003(2) 0.3104(15) 0.061(7) Uiso 1 1 d . . .
C14 C -0.0199(2) 0.26926(14) 0.22681(11) 0.0411(4) Uani 1 1 d . . .
H14A H -0.027(3) 0.300(2) 0.1748(16) 0.064(7) Uiso 1 1 d . . .
H14B H 0.086(3) 0.274(2) 0.2421(14) 0.057(6) Uiso 1 1 d . . .
H14C H -0.087(3) 0.313(2) 0.2604(15) 0.062(7) Uiso 1 1 d . . .
C15 C -0.2297(2) 0.1365(2) 0.20350(14) 0.0498(5) Uani 1 1 d . . .
H15A H -0.253(3) 0.057(3) 0.2086(18) 0.083(9) Uiso 1 1 d . . .
H15B H -0.240(3) 0.168(3) 0.1485(19) 0.081(9) Uiso 1 1 d . . .
H15C H -0.289(3) 0.181(2) 0.2406(15) 0.062(7) Uiso 1 1 d . . .
C16 C 0.0877(2) 0.05808(15) -0.05239(9) 0.0365(3) Uani 1 1 d . . .
C17 C -0.0510(4) 0.1098(3) -0.16471(17) 0.0895(10) Uani 1 1 d . . .
H17A H 0.0122 0.0644 -0.1997 0.134 Uiso 1 1 calc R . .
H17B H -0.0852 0.1793 -0.1924 0.134 Uiso 1 1 calc R . .
H17C H -0.1355 0.0629 -0.1489 0.134 Uiso 1 1 calc R . .
N1 N 0.34637(15) -0.01733(11) 0.07971(8) 0.0309(3) Uani 1 1 d . . .
N2 N 0.62373(14) -0.07079(11) 0.02863(8) 0.0329(3) Uani 1 1 d . . .
O1 O 0.31278(14) -0.19327(11) 0.13443(8) 0.0458(3) Uani 1 1 d . . .
O2 O 0.65979(14) 0.10890(10) -0.02021(9) 0.0473(3) Uani 1 1 d . . .
O3 O 0.23734(14) 0.10393(14) 0.20969(8) 0.0505(3) Uani 1 1 d . . .
O4 O 0.00570(13) 0.07754(10) 0.16500(6) 0.0347(2) Uani 1 1 d . . .
O5 O 0.07225(18) -0.04239(12) -0.06732(9) 0.0542(4) Uani 1 1 d . . .
O6 O 0.03147(19) 0.14393(13) -0.09512(8) 0.0587(4) Uani 1 1 d . . .
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'
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 122.91(15) . . ?
O1 C1 C2 120.44(14) . . ?
N1 C1 C2 116.31(13) . . ?
N2 C2 C1 115.46(12) . . ?
N2 C2 C3 102.32(13) . . ?
C1 C2 C3 119.04(14) . . ?
C2 C3 C4 101.14(14) . . ?
C3 C4 C5 105.35(15) . . ?
N2 C5 C4 104.03(14) . . ?
O2 C6 N2 123.12(15) . . ?
O2 C6 C7 119.57(14) . . ?
N2 C6 C7 117.26(13) . . ?
N1 C7 C6 114.74(12) . . ?
N1 C7 C8 103.07(13) . . ?
C6 C7 C8 113.93(13) . . ?
C7 C8 C9 104.87(13) . . ?
C16 C9 C8 107.68(14) . . ?
C16 C9 C10 111.84(13) . . ?
C8 C9 C10 106.01(13) . . ?
N1 C10 C11 112.54(13) . . ?
N1 C10 C9 104.09(12) . . ?
C11 C10 C9 110.46(12) . . ?
O3 C11 O4 127.18(15) . . ?
O3 C11 C10 124.58(15) . . ?
O4 C11 C10 108.20(13) . . ?
O4 C12 C13 110.04(13) . . ?
O4 C12 C15 102.45(13) . . ?
C13 C12 C15 111.72(17) . . ?
O4 C12 C14 109.59(14) . . ?
C13 C12 C14 112.74(15) . . ?
C15 C12 C14 109.81(16) . . ?
O5 C16 O6 124.11(17) . . ?
O5 C16 C9 125.32(16) . . ?
O6 C16 C9 110.54(14) . . ?
C1 N1 C10 121.94(13) . . ?
C1 N1 C7 127.31(14) . . ?
C10 N1 C7 110.60(12) . . ?
C6 N2 C2 127.38(13) . . ?
C6 N2 C5 120.96(14) . . ?
C2 N2 C5 109.36(13) . . ?
C11 O4 C12 121.70(12) . . ?
C16 O6 C17 116.17(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.219(2) . ?
C1 N1 1.346(2) . ?
C1 C2 1.515(2) . ?
C2 N2 1.469(2) . ?
C2 C3 1.519(2) . ?
C3 C4 1.529(3) . ?
C4 C5 1.538(3) . ?
C5 N2 1.469(2) . ?
C6 O2 1.225(2) . ?
C6 N2 1.341(2) . ?
C6 C7 1.508(2) . ?
C7 N1 1.469(2) . ?
C7 C8 1.526(2) . ?
C8 C9 1.554(2) . ?
C9 C16 1.510(2) . ?
C9 C10 1.555(2) . ?
C10 N1 1.449(2) . ?
C10 C11 1.527(2) . ?
C11 O3 1.195(2) . ?
C11 O4 1.335(2) . ?
C12 O4 1.4919(18) . ?
C12 C13 1.515(3) . ?
C12 C15 1.517(3) . ?
C12 C14 1.518(2) . ?
C16 O5 1.195(2) . ?
C16 O6 1.331(2) . ?
C17 O6 1.456(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658961
