#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/07/4500760.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_4500760
loop_
_publ_author_name
'Hisamatsu, Shugo'
'Masu, Hyuma'
'Azumaya, Isao'
'Takahashi, Masahiro'
'Kishikawa, Keiki'
'Kohmoto, Shigeo'
_publ_section_title
;
 U-Shaped Ureadicarboxylic Acid as a Versatile Folding Unit for
 Construction of Zigzag-type Architecture
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1453
_journal_paper_doi               10.1021/cg2002546
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C27 H24 N4 O5'
_chemical_formula_weight         484.50
_chemical_name_systematic
; 
 ? 
;
_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                 114.0950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.222(2)
_cell_length_b                   6.6626(7)
_cell_length_c                   18.9969(19)
_cell_measurement_reflns_used    4106
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      2.35
_cell_volume                     2336.5(4)
_computing_cell_refinement       'Smart (Bruker AXS)'
_computing_data_collection       'Smart (Bruker AXS)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker Smart1000 CCD area detector'
_diffrn_measurement_method       '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  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13437
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.10
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_correction_T_min  0.9809
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0399
_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)+(0.0445P)²+1.0202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                3948
_reflns_number_total             5247
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg2002546_si_002.cif
_cod_data_source_block           2(0062mas)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2336.4(4)
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4500760
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
_atom_site_refinement_flags
O2 O 0.22296(6) 0.31482(16) 0.28032(7) 0.0320(3) Uani 1 1 d .
H2 H 0.2532 0.2844 0.2622 0.048 Uiso 1 1 calc R
O1 O -0.01305(5) 0.73948(16) 0.50874(6) 0.0255(2) Uani 1 1 d .
O4 O 0.32598(6) 1.29352(16) 0.47238(7) 0.0294(3) Uani 1 1 d .
H4 H 0.3590 1.3378 0.4605 0.044 Uiso 1 1 calc R
O3 O 0.25396(6) 0.62753(18) 0.26323(7) 0.0354(3) Uani 1 1 d .
O5 O 0.38949(6) 1.00872(17) 0.49051(7) 0.0361(3) Uani 1 1 d .
N2 N 0.10768(6) 0.71204(19) 0.53711(7) 0.0221(3) Uani 1 1 d .
C15 C 0.33647(8) 1.1005(2) 0.48827(8) 0.0234(3) Uani 1 1 d .
C2 C 0.07086(8) 0.7161(2) 0.37734(8) 0.0209(3) Uani 1 1 d .
C4 C 0.14638(8) 0.7828(2) 0.30974(8) 0.0247(3) Uani 1 1 d .
H4A H 0.1664 0.8751 0.2856 0.030 Uiso 1 1 calc R
N1 N 0.02471(6) 0.78871(19) 0.41205(7) 0.0224(3) Uani 1 1 d .
C11 C 0.21851(8) 1.1119(2) 0.50301(8) 0.0219(3) Uani 1 1 d .
H11 H 0.2160 1.2522 0.4933 0.026 Uiso 1 1 calc R
C5 C 0.16572(8) 0.5808(2) 0.31506(8) 0.0213(3) Uani 1 1 d .
C12 C 0.27791(7) 1.0038(2) 0.50481(8) 0.0208(3) Uani 1 1 d .
C13 C 0.28215(8) 0.7991(2) 0.52129(9) 0.0238(3) Uani 1 1 d .
H13 H 0.3229 0.7242 0.5235 0.029 Uiso 1 1 calc R
C8 C 0.21868(8) 0.5125(2) 0.28377(8) 0.0241(3) Uani 1 1 d .
C9 C 0.16644(8) 0.8120(2) 0.52885(8) 0.0201(3) Uani 1 1 d .
C14 C 0.22740(8) 0.7047(2) 0.53441(8) 0.0232(3) Uani 1 1 d .
H14 H 0.2314 0.5661 0.5473 0.028 Uiso 1 1 calc R
C7 C 0.08842(8) 0.5136(2) 0.38124(8) 0.0226(3) Uani 1 1 d .
H7 H 0.0683 0.4215 0.4053 0.027 Uiso 1 1 calc R
C10 C 0.16299(8) 1.0179(2) 0.51512(8) 0.0224(3) Uani 1 1 d .
H10 H 0.1228 1.0934 0.5141 0.027 Uiso 1 1 calc R
C1 C 0.03646(8) 0.7461(2) 0.48727(8) 0.0204(3) Uani 1 1 d .
C6 C 0.13548(8) 0.4467(2) 0.34982(8) 0.0230(3) Uani 1 1 d .
H6 H 0.1472 0.3081 0.3520 0.028 Uiso 1 1 calc R
C17 C 0.12279(9) 0.5992(3) 0.60789(9) 0.0310(4) Uani 1 1 d .
H17A H 0.0779 0.5818 0.6152 0.047 Uiso 1 1 calc R
H17B H 0.1581 0.6726 0.6519 0.047 Uiso 1 1 calc R
H17C H 0.1425 0.4672 0.6041 0.047 Uiso 1 1 calc R
C3 C 0.09817(8) 0.8495(2) 0.33938(8) 0.0242(3) Uani 1 1 d .
H3 H 0.0837 0.9863 0.3338 0.029 Uiso 1 1 calc R
C16 C -0.04306(8) 0.8848(3) 0.36182(9) 0.0291(3) Uani 1 1 d .
H16A H -0.0701 0.9242 0.3922 0.044 Uiso 1 1 calc R
H16B H -0.0721 0.7906 0.3214 0.044 Uiso 1 1 calc R
H16C H -0.0325 1.0042 0.3381 0.044 Uiso 1 1 calc R
N3 N 0.42136(7) 0.4300(2) 0.42149(7) 0.0259(3) Uani 1 1 d .
N4 N 0.67828(7) 0.7045(2) 0.27179(7) 0.0274(3) Uani 1 1 d .
C23 C 0.57536(8) 0.5997(2) 0.32952(8) 0.0214(3) Uani 1 1 d .
C20 C 0.52211(8) 0.5423(2) 0.36178(8) 0.0211(3) Uani 1 1 d .
C27 C 0.59623(8) 0.7981(2) 0.32792(9) 0.0258(3) Uani 1 1 d .
H27 H 0.5754 0.9022 0.3464 0.031 Uiso 1 1 calc R
C24 C 0.60726(9) 0.4561(2) 0.29998(9) 0.0277(3) Uani 1 1 d .
H24 H 0.5942 0.3188 0.2989 0.033 Uiso 1 1 calc R
C26 C 0.64743(9) 0.8434(2) 0.29927(9) 0.0285(3) Uani 1 1 d .
H26 H 0.6612 0.9796 0.2992 0.034 Uiso 1 1 calc R
C21 C 0.47430(8) 0.6808(2) 0.37036(9) 0.0250(3) Uani 1 1 d .
H21 H 0.4755 0.8171 0.3563 0.030 Uiso 1 1 calc R
C19 C 0.51838(8) 0.3463(2) 0.38564(9) 0.0251(3) Uani 1 1 d .
H19 H 0.5502 0.2465 0.3817 0.030 Uiso 1 1 calc R
C25 C 0.65791(9) 0.5134(2) 0.27224(9) 0.0294(3) Uani 1 1 d .
H25 H 0.6792 0.4129 0.2527 0.035 Uiso 1 1 calc R
C22 C 0.42507(8) 0.6192(2) 0.39943(9) 0.0271(3) Uani 1 1 d .
H22 H 0.3924 0.7155 0.4040 0.033 Uiso 1 1 calc R
C18 C 0.46826(8) 0.2978(2) 0.41500(9) 0.0268(3) Uani 1 1 d .
H18 H 0.4670 0.1637 0.4314 0.032 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
C8 O2 H2 109.5
C15 O4 H4 109.5
C1 N2 C9 122.03(12)
C1 N2 C17 118.90(12)
C9 N2 C17 118.14(12)
O5 C15 O4 123.64(14)
O5 C15 C12 122.59(13)
O4 C15 C12 113.76(12)
C7 C2 C3 120.02(13)
C7 C2 N1 120.33(13)
C3 C2 N1 119.65(13)
C3 C4 C5 120.27(14)
C3 C4 H4A 119.9
C5 C4 H4A 119.9
C1 N1 C2 122.65(12)
C1 N1 C16 119.11(12)
C2 N1 C16 117.55(12)
C10 C11 C12 120.88(13)
C10 C11 H11 119.6
C12 C11 H11 119.6
C6 C5 C4 119.31(13)
C6 C5 C8 121.24(13)
C4 C5 C8 119.44(13)
C11 C12 C13 119.08(13)
C11 C12 C15 121.61(13)
C13 C12 C15 119.30(13)
C14 C13 C12 120.38(13)
C14 C13 H13 119.8
C12 C13 H13 119.8
O3 C8 O2 123.60(14)
O3 C8 C5 123.10(14)
O2 C8 C5 113.30(12)
C14 C9 C10 119.70(13)
C14 C9 N2 120.26(13)
C10 C9 N2 120.04(13)
C13 C14 C9 120.18(13)
C13 C14 H14 119.9
C9 C14 H14 119.9
C6 C7 C2 119.63(13)
C6 C7 H7 120.2
C2 C7 H7 120.2
C11 C10 C9 119.64(13)
C11 C10 H10 120.2
C9 C10 H10 120.2
O1 C1 N1 122.22(13)
O1 C1 N2 122.03(13)
N1 C1 N2 115.75(12)
C7 C6 C5 120.61(14)
C7 C6 H6 119.7
C5 C6 H6 119.7
N2 C17 H17A 109.5
N2 C17 H17B 109.5
H17A C17 H17B 109.5
N2 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C4 C3 C2 120.03(14)
C4 C3 H3 120.0
C2 C3 H3 120.0
N1 C16 H16A 109.5
N1 C16 H16B 109.5
H16A C16 H16B 109.5
N1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C18 N3 C22 117.30(13)
C26 N4 C25 117.52(13)
C27 C23 C24 116.68(13)
C27 C23 C20 121.95(13)
C24 C23 C20 121.37(13)
C21 C20 C19 116.73(13)
C21 C20 C23 122.06(13)
C19 C20 C23 121.20(13)
C26 C27 C23 119.83(14)
C26 C27 H27 120.1
C23 C27 H27 120.1
C25 C24 C23 120.01(14)
C25 C24 H24 120.0
C23 C24 H24 120.0
N4 C26 C27 123.09(15)
N4 C26 H26 118.5
C27 C26 H26 118.5
C22 C21 C20 119.83(14)
C22 C21 H21 120.1
C20 C21 H21 120.1
C18 C19 C20 119.79(14)
C18 C19 H19 120.1
C20 C19 H19 120.1
N4 C25 C24 122.85(14)
N4 C25 H25 118.6
C24 C25 H25 118.6
N3 C22 C21 123.03(14)
N3 C22 H22 118.5
C21 C22 H22 118.5
N3 C18 C19 123.29(14)
N3 C18 H18 118.4
C19 C18 H18 118.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C8 1.3229(19)
O2 H2 0.8400
O1 C1 1.2263(17)
O4 C15 1.3181(18)
O4 H4 0.8400
O3 C8 1.2150(18)
O5 C15 1.2199(18)
N2 C1 1.3816(18)
N2 C9 1.4257(17)
N2 C17 1.4600(19)
C15 C12 1.4900(19)
C2 C7 1.389(2)
C2 C3 1.393(2)
C2 N1 1.4291(17)
C4 C3 1.383(2)
C4 C5 1.394(2)
C4 H4A 0.9500
N1 C1 1.3790(18)
N1 C16 1.4597(19)
C11 C10 1.384(2)
C11 C12 1.3890(19)
C11 H11 0.9500
C5 C6 1.392(2)
C5 C8 1.4925(19)
C12 C13 1.394(2)
C13 C14 1.382(2)
C13 H13 0.9500
C9 C14 1.391(2)
C9 C10 1.393(2)
C14 H14 0.9500
C7 C6 1.3872(19)
C7 H7 0.9500
C10 H10 0.9500
C6 H6 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C3 H3 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
N3 C18 1.337(2)
N3 C22 1.340(2)
N4 C26 1.335(2)
N4 C25 1.339(2)
C23 C27 1.391(2)
C23 C24 1.394(2)
C23 C20 1.4900(19)
C20 C21 1.393(2)
C20 C19 1.394(2)
C27 C26 1.385(2)
C27 H27 0.9500
C24 C25 1.383(2)
C24 H24 0.9500
C26 H26 0.9500
C21 C22 1.383(2)
C21 H21 0.9500
C19 C18 1.380(2)
C19 H19 0.9500
C25 H25 0.9500
C22 H22 0.9500
C18 H18 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661306
