#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:44:53 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179594 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/58/4505812.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_4505812
loop_
_publ_author_name
'Luo, Tzy-Jiun M.'
'Palmore, G. Tayhas R.'
_publ_section_title
;
 Engineering Crystalline Architecture with Supramolecular Tapes: 
 Studies on Secondary Donor−Acceptor Interactions in Cocrystals of
 the Cyclic Dipeptide of Glycine
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              337
_journal_paper_doi               10.1021/cg025535d
_journal_volume                  2
_journal_year                    2002
_chemical_formula_sum            'C10 H10 N2 O6'
_chemical_formula_weight         254.20
_chemical_name_common            DKP.2PPA
_chemical_name_systematic
;
 diketopiperazine + propiolic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 102.958(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   9.3740(6)
_cell_length_b                   29.318(2)
_cell_length_c                   12.5881(9)
_cell_measurement_reflns_used    3145
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      31.3
_cell_measurement_theta_min      2.6
_cell_volume                     3371.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL 5.03, XP (Sheldrick, 1994)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32546
_diffrn_reflns_theta_full        31.51
_diffrn_reflns_theta_max         31.51
_diffrn_reflns_theta_min         1.39
_diffrn_standards_decay_%        <0.1
_diffrn_standards_number         '50 frames remeasured'
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.788
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     607
_refine_ls_number_reflns         10729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.788
_refine_ls_R_factor_all          0.1398
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0445P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                3995
_reflns_number_total             10729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg025535d_s1.cif
_cod_data_source_block           tl11fm
_cod_original_cell_volume        3371.4(4)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4505812
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1A O 1.04373(17) 0.12967(5) 0.84896(11) 0.0247(3) Uani 1 1 d
H1 H 0.863(3) 0.1692(8) 0.8970(17) 0.033(7) Uiso 1 1 d
O1B O 0.91140(17) 0.19098(5) 0.87231(12) 0.0241(3) Uani 1 1 d
C1 C 1.0190(2) 0.17040(7) 0.84141(15) 0.0174(4) Uani 1 1 d
C2 C 1.1102(2) 0.20115(7) 0.79473(15) 0.0181(4) Uani 1 1 d
C3 C 1.1864(3) 0.22479(8) 0.75393(17) 0.0233(5) Uani 1 1 d
H3 H 1.244(3) 0.2426(8) 0.7222(17) 0.035(7) Uiso 1 1 d
N1 N 0.5199(2) 0.11913(6) -0.03077(14) 0.0198(4) Uani 1 1 d
H1N H 0.522(3) 0.0916(8) -0.0516(17) 0.033(7) Uiso 1 1 d
N2 N 0.47539(19) 0.20925(6) 0.01419(14) 0.0194(4) Uani 1 1 d
H2N H 0.465(2) 0.2378(7) 0.0285(15) 0.020(6) Uiso 1 1 d
O7 O 0.26063(16) 0.19408(5) 0.05735(11) 0.0222(3) Uani 1 1 d
O9 O 0.73616(16) 0.13400(5) -0.07198(11) 0.0229(3) Uani 1 1 d
C7 C 0.3717(2) 0.18075(7) 0.02755(15) 0.0173(4) Uani 1 1 d
C8 C 0.3885(3) 0.13092(7) 0.00608(19) 0.0223(5) Uani 1 1 d
H8B H 0.388(3) 0.1146(8) 0.0716(19) 0.042(7) Uiso 1 1 d
H8A H 0.299(3) 0.1206(8) -0.0472(18) 0.042(7) Uiso 1 1 d
C9 C 0.6250(2) 0.14738(7) -0.04157(15) 0.0169(4) Uani 1 1 d
C10 C 0.6099(3) 0.19697(7) -0.01732(19) 0.0233(5) Uani 1 1 d
H10A H 0.624(3) 0.2128(7) -0.0800(17) 0.034(7) Uiso 1 1 d
H10B H 0.694(3) 0.2054(8) 0.0425(19) 0.050(8) Uiso 1 1 d
N3 N 1.0135(2) 0.12389(6) 0.48068(13) 0.0182(4) Uani 1 1 d
H3N H 1.015(3) 0.0945(9) 0.4616(19) 0.050(8) Uiso 1 1 d
N4 N 0.97413(19) 0.21580(6) 0.51396(14) 0.0185(4) Uani 1 1 d
H4N H 0.966(2) 0.2449(8) 0.5295(16) 0.031(7) Uiso 1 1 d
O14 O 1.19882(17) 0.13726(5) 0.39898(12) 0.0263(4) Uani 1 1 d
O16 O 0.78773(17) 0.20284(5) 0.59410(12) 0.0260(3) Uani 1 1 d
C14 C 1.1032(2) 0.15191(7) 0.44521(16) 0.0179(4) Uani 1 1 d
C15 C 1.0878(3) 0.20234(7) 0.45856(19) 0.0223(5) Uani 1 1 d
H15A H 1.067(3) 0.2160(8) 0.3863(17) 0.041(7) Uiso 1 1 d
H15B H 1.186(3) 0.2144(8) 0.4973(16) 0.034(6) Uiso 1 1 d
C16 C 0.8838(2) 0.18823(7) 0.54813(15) 0.0172(4) Uani 1 1 d
C17 C 0.8970(3) 0.13759(7) 0.53304(19) 0.0210(5) Uani 1 1 d
H17A H 0.916(2) 0.1238(7) 0.6088(16) 0.029(6) Uiso 1 1 d
H17B H 0.803(3) 0.1254(8) 0.4961(18) 0.046(8) Uiso 1 1 d
O4A O 0.43680(16) 0.20031(5) 0.59680(12) 0.0293(4) Uani 1 1 d
O4B O 0.61254(18) 0.14952(6) 0.66045(13) 0.0297(4) Uani 1 1 d
H4 H 0.674(3) 0.1693(9) 0.629(2) 0.057(9) Uiso 1 1 d
C4 C 0.4788(2) 0.16483(7) 0.64244(15) 0.0178(4) Uani 1 1 d
C5 C 0.3803(2) 0.13445(7) 0.68345(16) 0.0202(5) Uani 1 1 d
C6 C 0.2977(3) 0.11078(8) 0.71721(18) 0.0251(5) Uani 1 1 d
H6 H 0.224(3) 0.0920(8) 0.7432(17) 0.036(7) Uiso 1 1 d
O11A O 0.37786(17) 0.18905(6) 0.33139(13) 0.0296(4) Uani 1 1 d
O11B O 0.55099(17) 0.13791(5) 0.39968(12) 0.0285(4) Uani 1 1 d
H11 H 0.338(3) 0.1708(10) 0.366(2) 0.061(10) Uiso 1 1 d
C11 C 0.5109(2) 0.17289(7) 0.35072(15) 0.0180(4) Uani 1 1 d
C12 C 0.6107(2) 0.20172(7) 0.30666(16) 0.0203(4) Uani 1 1 d
C13 C 0.6959(3) 0.22369(8) 0.27029(17) 0.0256(5) Uani 1 1 d
H13 H 0.766(3) 0.2408(9) 0.2430(18) 0.053(8) Uiso 1 1 d
O18A O -0.04726(17) 0.19861(5) 0.13726(12) 0.0258(3) Uani 1 1 d
O18B O 0.08641(17) 0.13702(5) 0.11762(12) 0.0233(3) Uani 1 1 d
H18 H 0.145(3) 0.1587(9) 0.0939(19) 0.054(8) Uiso 1 1 d
C18 C -0.0217(2) 0.15798(7) 0.14732(15) 0.0167(4) Uani 1 1 d
C19 C -0.1146(3) 0.12773(7) 0.19506(16) 0.0192(5) Uani 1 1 d
C20 C -0.1936(3) 0.10587(8) 0.23654(17) 0.0239(5) Uani 1 1 d
H20 H -0.254(3) 0.0881(8) 0.2706(18) 0.039(7) Uiso 1 1 d
O21A O 1.05645(16) 0.03194(5) 0.40793(11) 0.0255(3) Uani 1 1 d
O21B O 0.88252(18) -0.01837(5) 0.33272(12) 0.0261(4) Uani 1 1 d
H21 H 0.827(3) 0.0021(10) 0.360(2) 0.065(10) Uiso 1 1 d
C21 C 1.0168(2) -0.00315(7) 0.35762(16) 0.0181(5) Uani 1 1 d
C22 C 1.1192(3) -0.03234(7) 0.31817(16) 0.0195(4) Uani 1 1 d
C23 C 1.2048(3) -0.05533(8) 0.28573(18) 0.0241(5) Uani 1 1 d
H23 H 1.273(3) -0.0735(8) 0.2605(19) 0.046(8) Uiso 1 1 d
O24A O 0.45985(16) -0.03339(5) 0.15293(11) 0.0229(3) Uani 1 1 d
O24B O 0.58339(16) 0.02818(5) 0.11761(11) 0.0218(3) Uani 1 1 d
H24 H 0.664(3) 0.0037(10) 0.094(2) 0.079(10) Uiso 1 1 d
C24 C 0.4803(2) 0.00751(7) 0.15457(15) 0.0165(4) Uani 1 1 d
C25 C 0.3869(3) 0.03871(7) 0.19946(16) 0.0184(4) Uani 1 1 d
C26 C 0.3080(3) 0.06136(8) 0.23957(17) 0.0220(5) Uani 1 1 d
H26 H 0.239(3) 0.0788(8) 0.2691(18) 0.042(8) Uiso 1 1 d
N6 N 0.9803(2) -0.04437(6) 0.03062(14) 0.0190(4) Uani 1 1 d
H6N H 0.977(3) -0.0737(8) 0.0561(18) 0.040(7) Uiso 1 1 d
O27 O 0.75994(16) -0.02879(5) 0.06410(11) 0.0208(3) Uani 1 1 d
C27 C 0.8723(2) -0.01618(7) 0.03480(15) 0.0164(4) Uani 1 1 d
C28 C 0.8852(3) 0.03280(8) 0.00286(19) 0.0225(5) Uani 1 1 d
H28A H 0.879(3) 0.0514(8) 0.0656(19) 0.046(8) Uiso 1 1 d
H28B H 0.800(3) 0.0396(8) -0.0570(18) 0.049(8) Uiso 1 1 d
N5 N 0.4834(2) -0.04600(6) 0.51805(13) 0.0185(4) Uani 1 1 d
H5N H 0.479(2) -0.0751(7) 0.5324(16) 0.027(7) Uiso 1 1 d
O29 O 0.70034(17) 0.03320(5) 0.39825(11) 0.0246(3) Uani 1 1 d
C29 C 0.6070(2) 0.01845(7) 0.44661(16) 0.0179(4) Uani 1 1 d
C30 C 0.5961(3) -0.03189(8) 0.46280(18) 0.0206(5) Uani 1 1 d
H30A H 0.693(3) -0.0422(7) 0.5040(16) 0.032(7) Uiso 1 1 d
H30B H 0.586(3) -0.0462(7) 0.3939(17) 0.032(7) Uiso 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'
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_1
_geom_angle_site_symmetry_3
O1A C1 O1B 125.2(2) . .
O1A C1 C2 121.4(2) . .
O1B C1 C2 113.38(19) . .
C3 C2 C1 177.1(2) . .
C9 N1 C8 126.20(18) . .
C7 N2 C10 126.02(18) . .
O7 C7 N2 121.91(19) . .
O7 C7 C8 119.21(19) . .
N2 C7 C8 118.9(2) . .
N1 C8 C7 114.85(18) . .
O9 C9 N1 121.85(19) . .
O9 C9 C10 119.30(19) . .
N1 C9 C10 118.84(19) . .
N2 C10 C9 115.09(18) . .
C14 N3 C17 125.49(19) . .
C16 N4 C15 125.95(18) . .
O14 C14 N3 121.36(19) . .
O14 C14 C15 119.26(19) . .
N3 C14 C15 119.4(2) . .
N4 C15 C14 114.93(18) . .
O16 C16 N4 121.73(19) . .
O16 C16 C17 118.99(19) . .
N4 C16 C17 119.28(19) . .
N3 C17 C16 114.93(19) . .
O4A C4 O4B 125.2(2) . .
O4A C4 C5 121.9(2) . .
O4B C4 C5 112.89(18) . .
C6 C5 C4 178.1(2) . .
O11B C11 O11A 125.2(2) . .
O11B C11 C12 122.1(2) . .
O11A C11 C12 112.70(18) . .
C13 C12 C11 177.2(2) . .
O18A C18 O18B 125.3(2) . .
O18A C18 C19 121.0(2) . .
O18B C18 C19 113.76(18) . .
C20 C19 C18 175.4(2) . .
O21A C21 O21B 125.3(2) . .
O21A C21 C22 121.7(2) . .
O21B C21 C22 113.06(18) . .
C23 C22 C21 178.5(2) . .
O24A C24 O24B 125.2(2) . .
O24A C24 C25 121.2(2) . .
O24B C24 C25 113.59(18) . .
C26 C25 C24 175.2(2) . .
C27 N6 C28 126.04(18) . 3_755
O27 C27 N6 122.23(19) . .
O27 C27 C28 119.07(19) . .
N6 C27 C28 118.71(19) . .
N6 C28 C27 115.25(19) 3_755 .
C29 N5 C30 125.46(18) 3_656 .
O29 C29 N5 121.71(19) . 3_656
O29 C29 C30 119.0(2) . .
N5 C29 C30 119.3(2) 3_656 .
N5 C30 C29 115.23(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1A C1 1.216(2) .
O1B C1 1.307(3) .
C1 C2 1.454(3) .
C2 C3 1.191(3) .
N1 C9 1.317(3) .
N1 C8 1.452(3) .
N2 C7 1.321(3) .
N2 C10 1.450(3) .
O7 C7 1.246(2) .
O9 C9 1.251(3) .
C7 C8 1.500(3) .
C9 C10 1.499(3) .
N3 C14 1.323(3) .
N3 C17 1.453(3) .
N4 C16 1.311(3) .
N4 C15 1.453(3) .
O14 C14 1.249(2) .
O16 C16 1.250(2) .
C14 C15 1.498(3) .
C16 C17 1.505(3) .
O4A C4 1.211(2) .
O4B C4 1.302(3) .
C4 C5 1.458(3) .
C5 C6 1.188(3) .
O11A C11 1.305(3) .
O11B C11 1.212(2) .
C11 C12 1.459(3) .
C12 C13 1.194(3) .
O18A C18 1.216(2) .
O18B C18 1.309(2) .
C18 C19 1.463(3) .
C19 C20 1.185(3) .
O21A C21 1.221(2) .
O21B C21 1.305(3) .
C21 C22 1.455(3) .
C22 C23 1.188(3) .
O24A C24 1.214(2) .
O24B C24 1.311(2) .
C24 C25 1.464(3) .
C25 C26 1.188(3) .
N6 C27 1.317(3) .
N6 C28 1.456(3) 3_755
O27 C27 1.248(2) .
C27 C28 1.503(3) .
C28 N6 1.456(3) 3_755
N5 C29 1.318(3) 3_656
N5 C30 1.450(3) .
O29 C29 1.249(2) .
C29 N5 1.318(3) 3_656
C29 C30 1.497(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1B H1 O9 0.88(2) 1.69(3) 2.549(2) 167(2) 1_556
N1 H1N O24A 0.85(2) 2.16(2) 2.975(2) 160(2) 3_655
N2 H2N O4A 0.87(2) 2.05(2) 2.900(2) 166.9(18) 4_565
N3 H3N O21A 0.89(3) 2.02(3) 2.904(2) 168(3) .
N4 H4N O18A 0.88(2) 2.16(2) 2.981(2) 154.0(18) 4_666
O4B H4 O16 0.96(3) 1.58(3) 2.540(2) 171(2) .
O11A H11 O14 0.83(3) 1.75(3) 2.547(2) 159(3) 1_455
O18B H18 O7 0.93(3) 1.64(3) 2.568(2) 175(3) .
O21B H21 O29 0.91(3) 1.65(3) 2.552(2) 169(3) .
O24B H24 O27 1.13(3) 1.41(3) 2.546(2) 177(3) .
N6 H6N O1A 0.92(2) 2.07(2) 2.959(2) 163(2) 3_756
N5 H5N O11B 0.88(2) 2.07(2) 2.930(2) 165(2) 3_656
