#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:44:53 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179594 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/58/4505814.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_4505814
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            'C18 H14 Cl4 N2 O6'
_chemical_formula_weight         496.12
_chemical_name_systematic
;
 diketopiperazine + 2,5-dichlorobenzoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.7800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.8469(2)
_cell_length_b                   6.1731(4)
_cell_length_c                   40.630(3)
_cell_measurement_temperature    90(2)
_cell_volume                     964.76(11)
_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 0.947
_diffrn_measured_fraction_theta_max 0.947
_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  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            8910
_diffrn_reflns_theta_full        31.46
_diffrn_reflns_theta_max         31.46
_diffrn_reflns_theta_min         1.00
_diffrn_standards_decay_%        <0.1
_diffrn_standards_number         '50 frames remeasured'
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  0.9743
_exptl_absorpt_correction_T_min  0.8801
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0464
_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)+(0.0368P)²+0.3422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                2174
_reflns_number_total             3042
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg025535d_s3.cif
_cod_data_source_block           tl24fm
_cod_original_cell_volume        964.78(10)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4505814
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C8 C 0.9886(16) 0.8030(14) 0.0191(2) 0.0141(13) Uani 0.50 1 d P A 1
O8 O 0.9717(12) 0.6369(6) 0.03616(9) 0.0221(8) Uani 0.50 1 d P A 1
C9 C 0.8692(17) 1.0155(17) 0.0336(2) 0.0131(14) Uani 0.50 1 d P . 1
H9A H 0.6269 0.9982 0.0411 0.026(15) Uiso 0.50 1 calc PR . 1
H9B H 1.0153 1.0483 0.0532 0.035(19) Uiso 0.50 1 calc PR . 1
N1 N 1.1171(12) 0.8004(7) -0.01119(9) 0.0168(8) Uani 0.50 1 d P . 1
H1N H 1.2011 0.6765 -0.0183 0.05(2) Uiso 0.50 1 calc PR . 1
C10 C 0.8610(16) 0.8129(14) 0.0159(2) 0.0140(13) Uani 0.50 1 d P B 2
O10 O 0.7425(11) 0.6500(6) 0.03067(8) 0.0185(7) Uani 0.50 1 d P B 2
C11 C 0.9900(17) 1.0001(18) 0.0359(2) 0.0154(15) Uani 0.50 1 d P . 2
H11A H 0.7968 1.0545 0.0495 0.010(14) Uiso 0.50 1 calc PR . 2
H11B H 1.1751 0.9479 0.0511 0.040(19) Uiso 0.50 1 calc PR . 2
N2 N 0.8737(12) 0.8213(7) -0.01681(9) 0.0166(8) Uani 0.50 1 d P . 2
H2N H 0.7925 0.7088 -0.0278 0.039(19) Uiso 0.50 1 calc PR . 2
Cl1 Cl 0.12839(14) -0.00847(10) 0.122838(14) 0.01682(13) Uani 1 1 d . . .
Cl2 Cl 0.66319(15) 0.70338(10) 0.219814(14) 0.01834(14) Uani 1 1 d . . .
C1 C 0.4565(5) 0.3827(4) 0.13589(5) 0.0121(4) Uani 1 1 d . . .
C2 C 0.2874(6) 0.1976(4) 0.14773(5) 0.0137(4) Uani 1 1 d . . .
C3 C 0.2357(6) 0.1704(4) 0.18146(6) 0.0168(5) Uani 1 1 d . . .
H3 H 0.133(8) 0.049(5) 0.1896(7) 0.032(8) Uiso 1 1 d . . .
C4 C 0.3505(6) 0.3252(4) 0.20370(6) 0.0159(5) Uani 1 1 d . . .
H4 H 0.320(8) 0.309(5) 0.2282(7) 0.027(8) Uiso 1 1 d . . .
C5 C 0.5155(6) 0.5076(4) 0.19187(5) 0.0149(4) Uani 1 1 d . . .
C6 C 0.5703(6) 0.5378(4) 0.15864(6) 0.0132(4) Uani 1 1 d . . .
H6 H 0.684(7) 0.667(5) 0.1527(6) 0.017(7) Uiso 1 1 d . . .
C7 C 0.5240(6) 0.4193(4) 0.09992(6) 0.0146(4) Uani 1 1 d . . .
H7 H 0.780(9) 0.610(6) 0.0750(8) 0.043(10) Uiso 1 1 d . . .
O7A O 0.4151(5) 0.3060(3) 0.07792(4) 0.0209(4) Uani 1 1 d . . .
O7B O 0.7210(5) 0.5924(3) 0.09526(4) 0.0222(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'
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'
Cl Cl 0.1484 0.1585 '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
O8 C8 N1 121.9(7) . .
O8 C8 C9 118.8(7) . .
N1 C8 C9 119.2(7) . .
N1 C9 C8 114.9(7) 3_775 .
N1 C9 H9A 108.5 3_775 .
C8 C9 H9A 108.5 . .
N1 C9 H9B 108.5 3_775 .
C8 C9 H9B 108.5 . .
H9A C9 H9B 107.5 . .
C8 N1 C9 125.7(6) . 3_775
C8 N1 H1N 117.1 . .
C9 N1 H1N 117.1 3_775 .
O10 C10 N2 121.7(7) . .
O10 C10 C11 118.5(7) . .
N2 C10 C11 119.8(7) . .
N2 C11 C10 114.7(7) 3_775 .
N2 C11 H11A 108.6 3_775 .
C10 C11 H11A 108.6 . .
N2 C11 H11B 108.6 3_775 .
C10 C11 H11B 108.6 . .
H11A C11 H11B 107.6 . .
C10 N2 C11 125.5(6) . 3_775
C10 N2 H2N 117.2 . .
C11 N2 H2N 117.2 3_775 .
C6 C1 C2 118.3(2) . .
C6 C1 C7 118.9(2) . .
C2 C1 C7 122.8(2) . .
C3 C2 C1 120.5(2) . .
C3 C2 Cl1 115.50(19) . .
C1 C2 Cl1 124.04(17) . .
C4 C3 C2 120.6(2) . .
C4 C3 H3 117.7(19) . .
C2 C3 H3 121.6(19) . .
C5 C4 C3 118.6(2) . .
C5 C4 H4 119.1(17) . .
C3 C4 H4 122.3(17) . .
C6 C5 C4 121.8(2) . .
C6 C5 Cl2 119.25(19) . .
C4 C5 Cl2 118.95(17) . .
C5 C6 C1 120.2(2) . .
C5 C6 H6 116.4(16) . .
C1 C6 H6 123.4(16) . .
O7A C7 O7B 123.8(2) . .
O7A C7 C1 124.7(2) . .
O7B C7 C1 111.5(2) . .
C7 O7B H7 113(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C8 O8 1.240(9) .
C8 N1 1.333(9) .
C8 C9 1.512(13) .
C9 N1 1.457(10) 3_775
C9 H9A 0.9900 .
C9 H9B 0.9900 .
N1 C9 1.457(10) 3_775
N1 H1N 0.8800 .
C10 O10 1.260(9) .
C10 N2 1.331(9) .
C10 C11 1.493(14) .
C11 N2 1.450(11) 3_775
C11 H11A 0.9900 .
C11 H11B 0.9900 .
N2 C11 1.450(11) 3_775
N2 H2N 0.8800 .
Cl1 C2 1.732(2) .
Cl2 C5 1.748(2) .
C1 C6 1.397(3) .
C1 C2 1.403(3) .
C1 C7 1.505(3) .
C2 C3 1.398(3) .
C3 C4 1.383(3) .
C3 H3 0.91(3) .
C4 C5 1.382(3) .
C4 H4 1.01(3) .
C5 C6 1.382(3) .
C6 H6 0.94(3) .
C7 O7A 1.206(3) .
C7 O7B 1.325(3) .
O7B H7 0.86(3) .
