#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:42:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178439 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/60/4026043.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_4026043
loop_
_publ_author_name
'Shin Ando'
'Amy L. Grote'
'Kazunori Koide'
_publ_section_title
;
 Diastereoselective Synthesis of Diketopiperazine Bis-α,β-epoxides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1155
_journal_page_last               1158
_journal_paper_doi               10.1021/jo102096d
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 91.927(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   14.326(4)
_cell_length_b                   15.140(4)
_cell_length_c                   24.246(6)
_cell_measurement_reflns_used    4794
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      26.07
_cell_measurement_theta_min      2.55
_cell_volume                     5256(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            32650
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.42
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       anit-prism
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         8866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1663
_reflns_number_gt                5655
_reflns_number_total             8866
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102096d_si_002.cif
_cod_data_source_block           sa3036s
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4026043
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
N1 N 0.86049(8) 0.15313(7) 0.50953(5) 0.0299(3) Uani 1 1 d .
O1 O 0.88775(7) 0.25263(7) 0.57828(4) 0.0373(3) Uani 1 1 d .
C1 C 0.87457(9) 0.17682(9) 0.56255(6) 0.0283(3) Uani 1 1 d .
O2 O 0.92229(8) -0.07276(7) 0.50919(5) 0.0476(3) Uani 1 1 d .
C2 C 0.83818(10) 0.06236(9) 0.49588(6) 0.0313(3) Uani 1 1 d .
N2 N 0.91033(9) 0.01957(8) 0.58243(6) 0.0361(3) Uani 1 1 d .
O3 O 0.82629(8) 0.04491(7) 0.43926(4) 0.0422(3) Uani 1 1 d .
C3 C 0.89482(10) -0.00426(10) 0.52917(7) 0.0347(3) Uani 1 1 d .
N3 N 0.44105(8) 0.06231(8) 0.20328(5) 0.0313(3) Uani 1 1 d .
O4 O 0.89638(7) 0.12102(8) 0.65791(4) 0.0398(3) Uani 1 1 d .
C4 C 0.87086(10) 0.10039(9) 0.60297(6) 0.0304(3) Uani 1 1 d .
C5 C 0.74367(11) 0.04079(10) 0.47240(6) 0.0348(3) Uani 1 1 d .
H5A H 0.7013 0.0922 0.4681 0.042 Uiso 1 1 calc R
O5 O 0.31845(7) 0.04431(7) 0.25953(5) 0.0387(3) Uani 1 1 d .
C6 C 0.69567(11) -0.04517(10) 0.47840(6) 0.0344(3) Uani 1 1 d .
O6 O 0.57307(8) 0.08383(7) 0.14686(4) 0.0367(2) Uani 1 1 d .
C7 C 0.72483(12) -0.12130(11) 0.45249(7) 0.0411(4) Uani 1 1 d .
H7A H 0.7772 -0.1200 0.4302 0.049 Uiso 1 1 calc R
C8 C 0.67635(13) -0.19945(11) 0.45969(8) 0.0463(4) Uani 1 1 d .
H8A H 0.6959 -0.2510 0.4418 0.056 Uiso 1 1 calc R
C9 C 0.59987(13) -0.20271(12) 0.49265(7) 0.0473(4) Uani 1 1 d .
H9A H 0.5683 -0.2564 0.4978 0.057 Uiso 1 1 calc R
C10 C 0.56988(13) -0.12676(12) 0.51812(8) 0.0487(4) Uani 1 1 d .
H10A H 0.5174 -0.1284 0.5403 0.058 Uiso 1 1 calc R
C11 C 0.61731(12) -0.04807(11) 0.51085(7) 0.0429(4) Uani 1 1 d .
H11A H 0.5965 0.0037 0.5279 0.052 Uiso 1 1 calc R
C12 C 0.79999(10) 0.09653(10) 0.64640(6) 0.0344(3) Uani 1 1 d .
H12A H 0.7842 0.0359 0.6581 0.041 Uiso 1 1 calc R
C13 C 0.72583(10) 0.16278(10) 0.65624(6) 0.0318(3) Uani 1 1 d .
C14 C 0.63367(11) 0.13489(10) 0.65057(7) 0.0389(3) Uani 1 1 d .
H14A H 0.6201 0.0771 0.6385 0.047 Uiso 1 1 calc R
C15 C 0.56168(11) 0.19196(11) 0.66261(8) 0.0457(4) Uani 1 1 d .
H15A H 0.4993 0.1732 0.6582 0.055 Uiso 1 1 calc R
C16 C 0.58129(12) 0.27634(11) 0.68102(7) 0.0438(4) Uani 1 1 d .
H16A H 0.5323 0.3146 0.6899 0.053 Uiso 1 1 calc R
C17 C 0.67305(12) 0.30477(11) 0.68646(7) 0.0409(4) Uani 1 1 d .
H17A H 0.6863 0.3625 0.6986 0.049 Uiso 1 1 calc R
C18 C 0.74548(11) 0.24816(11) 0.67399(6) 0.0372(3) Uani 1 1 d .
H18A H 0.8077 0.2676 0.6775 0.045 Uiso 1 1 calc R
C19 C 0.86009(12) 0.21925(10) 0.46559(6) 0.0380(3) Uani 1 1 d .
H19A H 0.8763 0.2765 0.4811 0.057 Uiso 1 1 calc R
H19B H 0.7984 0.2222 0.4480 0.057 Uiso 1 1 calc R
H19C H 0.9053 0.2030 0.4385 0.057 Uiso 1 1 calc R
C20 C 0.96030(13) -0.04047(13) 0.62031(8) 0.0546(5) Uani 1 1 d .
H20A H 0.9821 -0.0912 0.6000 0.082 Uiso 1 1 calc R
H20B H 0.9186 -0.0600 0.6486 0.082 Uiso 1 1 calc R
H20C H 1.0133 -0.0100 0.6374 0.082 Uiso 1 1 calc R
C21 C 0.39965(10) 0.06352(9) 0.25282(6) 0.0300(3) Uani 1 1 d .
C22 C 0.38640(12) 0.04554(11) 0.15223(6) 0.0386(4) Uani 1 1 d .
H22A H 0.3242 0.0259 0.1612 0.058 Uiso 1 1 calc R
H22B H 0.4168 0.0001 0.1311 0.058 Uiso 1 1 calc R
H22C H 0.3820 0.0994 0.1307 0.058 Uiso 1 1 calc R
C23 C 0.53641(10) 0.09232(9) 0.19949(5) 0.0286(3) Uani 1 1 d .
C24 C 0.55708(10) 0.17268(9) 0.16653(6) 0.0323(3) Uani 1 1 d .
H24A H 0.5016 0.2024 0.1497 0.039 Uiso 1 1 calc R
C25 C 0.63913(10) 0.23090(10) 0.17694(6) 0.0327(3) Uani 1 1 d .
C26 C 0.72953(11) 0.20152(11) 0.16948(7) 0.0409(4) Uani 1 1 d .
H26A H 0.7402 0.1439 0.1568 0.049 Uiso 1 1 calc R
C27 C 0.80394(12) 0.25762(12) 0.18088(8) 0.0465(4) Uani 1 1 d .
H27A H 0.8652 0.2378 0.1758 0.056 Uiso 1 1 calc R
C28 C 0.78933(12) 0.34202(11) 0.19959(7) 0.0447(4) Uani 1 1 d .
H28A H 0.8404 0.3791 0.2081 0.054 Uiso 1 1 calc R
C29 C 0.69953(12) 0.37195(11) 0.20578(7) 0.0433(4) Uani 1 1 d .
H29A H 0.6893 0.4301 0.2177 0.052 Uiso 1 1 calc R
C30 C 0.62419(11) 0.31673(10) 0.19447(7) 0.0391(4) Uani 1 1 d .
H30A H 0.5630 0.3375 0.1987 0.047 Uiso 1 1 calc R
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'
H H 0.0000 0.0000 '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'
O O 0.0106 0.0060 '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_site_symmetry_3
C1 N1 C2 119.83(12) .
C1 N1 C19 120.76(12) .
C2 N1 C19 119.24(12) .
O1 C1 N1 124.47(13) .
O1 C1 C4 121.51(13) .
N1 C1 C4 114.01(12) .
O3 C2 N1 114.92(12) .
O3 C2 C5 60.33(9) .
N1 C2 C5 119.16(12) .
O3 C2 C3 116.26(12) .
N1 C2 C3 113.66(12) .
C5 C2 C3 121.57(12) .
C3 N2 C4 120.13(12) .
C3 N2 C20 119.69(14) .
C4 N2 C20 119.96(14) .
C2 O3 C5 62.72(9) .
O2 C3 N2 124.27(15) .
O2 C3 C2 122.13(15) .
N2 C3 C2 113.59(12) .
C21 N3 C23 119.59(12) .
C21 N3 C22 120.88(13) .
C23 N3 C22 118.71(12) .
C4 O4 C12 62.88(9) .
O4 C4 N2 115.04(12) .
O4 C4 C12 59.98(9) .
N2 C4 C12 119.69(12) .
O4 C4 C1 115.40(12) .
N2 C4 C1 113.62(12) .
C12 C4 C1 121.74(12) .
O3 C5 C6 118.75(12) .
O3 C5 C2 56.95(9) .
C6 C5 C2 125.09(13) .
O3 C5 H5A 114.5 .
C6 C5 H5A 114.5 .
C2 C5 H5A 114.5 .
C7 C6 C11 119.43(14) .
C7 C6 C5 122.61(14) .
C11 C6 C5 117.95(14) .
C23 O6 C24 63.06(9) .
C8 C7 C6 119.58(15) .
C8 C7 H7A 120.2 .
C6 C7 H7A 120.2 .
C9 C8 C7 121.00(16) .
C9 C8 H8A 119.5 .
C7 C8 H8A 119.5 .
C8 C9 C10 119.66(16) .
C8 C9 H9A 120.2 .
C10 C9 H9A 120.2 .
C9 C10 C11 119.87(17) .
C9 C10 H10A 120.1 .
C11 C10 H10A 120.1 .
C10 C11 C6 120.45(15) .
C10 C11 H11A 119.8 .
C6 C11 H11A 119.8 .
O4 C12 C13 118.59(13) .
O4 C12 C4 57.14(9) .
C13 C12 C4 126.55(12) .
O4 C12 H12A 114.1 .
C13 C12 H12A 114.1 .
C4 C12 H12A 114.1 .
C18 C13 C14 119.75(14) .
C18 C13 C12 122.66(14) .
C14 C13 C12 117.47(14) .
C15 C14 C13 120.13(16) .
C15 C14 H14A 119.9 .
C13 C14 H14A 119.9 .
C16 C15 C14 120.09(16) .
C16 C15 H15A 120.0 .
C14 C15 H15A 120.0 .
C15 C16 C17 120.07(15) .
C15 C16 H16A 120.0 .
C17 C16 H16A 120.0 .
C16 C17 C18 120.11(16) .
C16 C17 H17A 119.9 .
C18 C17 H17A 119.9 .
C17 C18 C13 119.84(15) .
C17 C18 H18A 120.1 .
C13 C18 H18A 120.1 .
N1 C19 H19A 109.5 .
N1 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
N1 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
N2 C20 H20A 109.5 .
N2 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
N2 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
O5 C21 N3 124.32(14) .
O5 C21 C23 121.57(13) 2_655
N3 C21 C23 114.10(12) 2_655
N3 C22 H22A 109.5 .
N3 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
N3 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
O6 C23 N3 114.38(11) .
O6 C23 C24 59.98(9) .
N3 C23 C24 119.72(12) .
O6 C23 C21 115.65(12) 2_655
N3 C23 C21 114.17(11) 2_655
C24 C23 C21 121.21(12) 2_655
O6 C24 C25 118.34(12) .
O6 C24 C23 56.96(8) .
C25 C24 C23 124.33(13) .
O6 C24 H24A 114.9 .
C25 C24 H24A 114.9 .
C23 C24 H24A 114.9 .
C26 C25 C30 119.68(14) .
C26 C25 C24 121.67(14) .
C30 C25 C24 118.65(14) .
C27 C26 C25 119.57(16) .
C27 C26 H26A 120.2 .
C25 C26 H26A 120.2 .
C28 C27 C26 120.79(16) .
C28 C27 H27A 119.6 .
C26 C27 H27A 119.6 .
C27 C28 C29 119.68(15) .
C27 C28 H28A 120.2 .
C29 C28 H28A 120.2 .
C28 C29 C30 120.29(16) .
C28 C29 H29A 119.9 .
C30 C29 H29A 119.9 .
C29 C30 C25 119.94(15) .
C29 C30 H30A 120.0 .
C25 C30 H30A 120.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3433(18) .
N1 C2 1.4469(18) .
N1 C19 1.4617(18) .
O1 C1 1.2221(17) .
C1 C4 1.518(2) .
O2 C3 1.2157(18) .
C2 O3 1.4027(18) .
C2 C5 1.487(2) .
C2 C3 1.511(2) .
N2 C3 1.352(2) .
N2 C4 1.4435(19) .
N2 C20 1.462(2) .
O3 C5 1.4542(19) .
N3 C21 1.3575(18) .
N3 C23 1.4455(18) .
N3 C22 1.4643(19) .
O4 C4 1.4045(18) .
O4 C12 1.4478(18) .
C4 C12 1.488(2) .
C5 C6 1.481(2) .
C5 H5A 0.9900 .
O5 C21 1.2154(17) .
C6 C7 1.384(2) .
C6 C11 1.393(2) .
O6 C23 1.4020(16) .
O6 C24 1.4481(18) .
C7 C8 1.386(2) .
C7 H7A 0.9400 .
C8 C9 1.379(3) .
C8 H8A 0.9400 .
C9 C10 1.381(3) .
C9 H9A 0.9400 .
C10 C11 1.386(2) .
C10 H10A 0.9400 .
C11 H11A 0.9400 .
C12 C13 1.486(2) .
C12 H12A 0.9900 .
C13 C18 1.388(2) .
C13 C14 1.389(2) .
C14 C15 1.384(2) .
C14 H14A 0.9400 .
C15 C16 1.379(2) .
C15 H15A 0.9400 .
C16 C17 1.385(2) .
C16 H16A 0.9400 .
C17 C18 1.387(2) .
C17 H17A 0.9400 .
C18 H18A 0.9400 .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C19 H19C 0.9700 .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C20 H20C 0.9700 .
C21 C23 1.515(2) 2_655
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C22 H22C 0.9700 .
C23 C24 1.4909(19) .
C23 C21 1.515(2) 2_655
C24 C25 1.484(2) .
C24 H24A 0.9900 .
C25 C26 1.387(2) .
C25 C30 1.386(2) .
C26 C27 1.384(2) .
C26 H26A 0.9400 .
C27 C28 1.374(3) .
C27 H27A 0.9400 .
C28 C29 1.377(2) .
C28 H28A 0.9400 .
C29 C30 1.385(2) .
C29 H29A 0.9400 .
C30 H30A 0.9400 .
