#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/42/4024219.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_4024219
loop_
_publ_author_name
'Jun Yang'
'Mahender B. Dewal'
'David Sobransingh'
'Mark D. Smith'
'Yuewen Xu'
'Linda S. Shimizu'
_publ_section_title
;
Examination of the Structural Features That Favor the Columnar
Self-Assembly of Bis-urea Macrocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              102
_journal_page_last               110
_journal_paper_doi               10.1021/jo801717w
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C16 H24 N4 O4'
_chemical_formula_sum            'C16 H24 N4 O4'
_chemical_formula_weight         336.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.029(2)
_cell_angle_beta                 112.7490(10)
_cell_angle_gamma                91.4500(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1218(6)
_cell_length_b                   9.8426(7)
_cell_length_c                   10.7786(7)
_cell_measurement_reflns_used    1751
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      21.843
_cell_measurement_theta_min      2.436
_cell_volume                     870.68(10)
_computing_cell_refinement       'SAINT+ NT V6.22 (Bruker, 2001)'
_computing_data_collection       'SMART NT V5.625 (Bruker, 1998)'
_computing_data_reduction        'SAINT+ NT V6.22'
_computing_molecular_graphics    'SHELXTL V6.1 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_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  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7042
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0450
_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)+(0.0671P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                1628
_reflns_number_total             2497
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801717w_si_001.cif
_cod_data_source_block           pbu04am
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               4024219
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.3156(3) 0.5775(3) 0.2851(3) 0.0469(6) Uani 1 1 d . . .
C2 C 0.1861(3) 0.3562(3) 0.1250(3) 0.0584(7) Uani 1 1 d . . .
H2A H 0.2883 0.3485 0.1177 0.070 Uiso 1 1 calc R . .
H2B H 0.1036 0.3355 0.0322 0.070 Uiso 1 1 calc R . .
C3 C 0.1619(2) 0.2482(3) 0.1990(2) 0.0442(6) Uani 1 1 d . . .
C4 C 0.1543(3) 0.1089(3) 0.1399(3) 0.0592(7) Uani 1 1 d . . .
H4A H 0.1621 0.0844 0.0551 0.071 Uiso 1 1 calc R . .
C5 C 0.1355(3) 0.0061(3) 0.2048(3) 0.0718(8) Uani 1 1 d . . .
H5 H 0.1306 -0.0869 0.1636 0.086 Uiso 1 1 calc R . .
C6 C 0.1238(3) 0.0403(3) 0.3291(3) 0.0645(8) Uani 1 1 d . . .
H6 H 0.1127 -0.0298 0.3728 0.077 Uiso 1 1 calc R . .
C7 C 0.1283(3) 0.1782(3) 0.3910(3) 0.0499(7) Uani 1 1 d . . .
C8 C 0.1477(2) 0.2812(3) 0.3239(2) 0.0489(7) Uani 1 1 d . . .
H8 H 0.1510 0.3743 0.3644 0.059 Uiso 1 1 calc R . .
C9 C 0.1079(3) 0.2141(3) 0.5244(3) 0.0654(8) Uani 1 1 d . . .
H9A H -0.0008 0.2356 0.5055 0.079 Uiso 1 1 calc R . .
H9B H 0.1234 0.1334 0.5656 0.079 Uiso 1 1 calc R . .
C10 C 0.1890(3) 0.4034(3) 0.7272(3) 0.0491(6) Uani 1 1 d . . .
C11 C 0.2830(4) 0.5997(3) 0.9245(3) 0.0766(9) Uani 1 1 d . . .
H11A H 0.2825 0.5474 0.9921 0.092 Uiso 1 1 calc R . .
H11B H 0.1811 0.6372 0.8907 0.092 Uiso 1 1 calc R . .
C12 C 0.4109(4) 0.7141(3) 0.9908(3) 0.0839(10) Uani 1 1 d . . .
H12A H 0.3898 0.7754 1.0626 0.101 Uiso 1 1 calc R . .
H12B H 0.5106 0.6765 1.0348 0.101 Uiso 1 1 calc R . .
C13 C 0.3089(4) 0.8758(4) 0.8517(3) 0.0889(10) Uani 1 1 d . . .
H13A H 0.3018 0.9400 0.9290 0.107 Uiso 1 1 calc R . .
H13B H 0.2081 0.8169 0.8032 0.107 Uiso 1 1 calc R . .
C14 C 0.3359(4) 0.9562(3) 0.7571(3) 0.0886(10) Uani 1 1 d . . .
H14A H 0.2709 1.0332 0.7512 0.106 Uiso 1 1 calc R . .
H14B H 0.4470 0.9956 0.7976 0.106 Uiso 1 1 calc R . .
C15 C 0.4226(4) 0.8029(4) 0.6085(3) 0.0930(11) Uani 1 1 d . . .
H15A H 0.4087 0.7112 0.6256 0.112 Uiso 1 1 calc R . .
H15B H 0.5258 0.8487 0.6757 0.112 Uiso 1 1 calc R . .
C16 C 0.4180(3) 0.7890(3) 0.4674(3) 0.0817(10) Uani 1 1 d . . .
H16A H 0.4088 0.8800 0.4447 0.098 Uiso 1 1 calc R . .
H16B H 0.5190 0.7599 0.4678 0.098 Uiso 1 1 calc R . .
N1 N 0.2906(3) 0.6927(2) 0.3607(2) 0.0628(7) Uani 1 1 d . . .
H1 H 0.198(3) 0.701(2) 0.356(3) 0.059(8) Uiso 1 1 d . . .
N2 N 0.1825(3) 0.4985(2) 0.1896(2) 0.0503(6) Uani 1 1 d . . .
H2 H 0.097(3) 0.519(2) 0.190(2) 0.046(7) Uiso 1 1 d . . .
N3 N 0.2169(3) 0.3304(3) 0.6219(2) 0.0589(7) Uani 1 1 d . . .
H3 H 0.305(3) 0.348(3) 0.619(2) 0.059(8) Uiso 1 1 d . . .
N4 N 0.3006(3) 0.5073(3) 0.8117(2) 0.0605(7) Uani 1 1 d . . .
H4 H 0.373(3) 0.526(2) 0.794(2) 0.041(7) Uiso 1 1 d . . .
O1 O 0.45066(19) 0.54687(18) 0.29960(18) 0.0648(6) Uani 1 1 d . . .
O2 O 0.0667(2) 0.37570(19) 0.74597(19) 0.0667(6) Uani 1 1 d . . .
O3 O 0.4302(2) 0.7944(2) 0.90021(19) 0.0684(6) Uani 1 1 d . . .
O4 O 0.3012(2) 0.8805(2) 0.6233(2) 0.0847(7) 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'
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 122.6(2) . . ?
O1 C1 N2 121.9(3) . . ?
N1 C1 N2 115.4(2) . . ?
N2 C2 C3 115.1(2) . . ?
N2 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
N2 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C8 C3 C4 118.2(2) . . ?
C8 C3 C2 123.1(2) . . ?
C4 C3 C2 118.7(2) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.7(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 118.3(2) . . ?
C6 C7 C9 120.2(2) . . ?
C8 C7 C9 121.4(2) . . ?
C3 C8 C7 121.5(2) . . ?
C3 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
N3 C9 C7 113.7(2) . . ?
N3 C9 H9A 108.8 . . ?
C7 C9 H9A 108.8 . . ?
N3 C9 H9B 108.8 . . ?
C7 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O2 C10 N4 121.8(3) . . ?
O2 C10 N3 121.9(3) . . ?
N4 C10 N3 116.3(2) . . ?
N4 C11 C12 112.3(2) . . ?
N4 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N4 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
O3 C12 C11 114.6(2) . . ?
O3 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
O3 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
O3 C13 C14 111.8(3) . . ?
O3 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
O3 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
O4 C14 C13 115.6(3) . . ?
O4 C14 H14A 108.4 . . ?
C13 C14 H14A 108.4 . . ?
O4 C14 H14B 108.4 . . ?
C13 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?
O4 C15 C16 110.4(3) . . ?
O4 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
O4 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N1 C16 C15 115.3(3) . . ?
N1 C16 H16A 108.4 . . ?
C15 C16 H16A 108.4 . . ?
N1 C16 H16B 108.4 . . ?
C15 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
C1 N1 C16 123.2(2) . . ?
C1 N1 H1 117.8(17) . . ?
C16 N1 H1 118.0(17) . . ?
C1 N2 C2 121.9(2) . . ?
C1 N2 H2 117.7(16) . . ?
C2 N2 H2 116.2(16) . . ?
C10 N3 C9 122.2(2) . . ?
C10 N3 H3 117.7(17) . . ?
C9 N3 H3 119.7(17) . . ?
C10 N4 C11 122.6(2) . . ?
C10 N4 H4 119.4(17) . . ?
C11 N4 H4 117.4(17) . . ?
C13 O3 C12 114.5(2) . . ?
C14 O4 C15 115.0(2) . . ?
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 1.234(3) . ?
C1 N1 1.344(3) . ?
C1 N2 1.348(3) . ?
C2 N2 1.447(3) . ?
C2 C3 1.504(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.380(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.378(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.364(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.398(3) . ?
C7 C9 1.497(3) . ?
C8 H8 0.9300 . ?
C9 N3 1.441(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O2 1.241(3) . ?
C10 N4 1.337(3) . ?
C10 N3 1.337(3) . ?
C11 N4 1.437(3) . ?
C11 C12 1.456(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O3 1.425(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.378(3) . ?
C13 C14 1.489(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O4 1.400(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O4 1.403(3) . ?
C15 C16 1.484(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N1 1.437(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
N1 H1 0.83(3) . ?
N2 H2 0.82(2) . ?
N3 H3 0.83(2) . ?
N4 H4 0.78(2) . ?
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
N1 H1 O2 0.83(3) 2.26(3) 3.015(3) 150(2) 2_566
N2 H2 O2 0.82(2) 2.09(2) 2.867(3) 159(2) 2_566
N3 H3 O1 0.83(2) 2.19(2) 2.968(3) 154(2) 2_666
N4 H4 O1 0.78(2) 2.27(2) 2.965(3) 149(2) 2_666
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C2 C3 C8 -4.0(3) . . . . ?
N2 C2 C3 C4 176.3(2) . . . . ?
C8 C3 C4 C5 -0.9(4) . . . . ?
C2 C3 C4 C5 178.7(2) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C5 C6 C7 C9 177.2(2) . . . . ?
C4 C3 C8 C7 0.9(3) . . . . ?
C2 C3 C8 C7 -178.8(2) . . . . ?
C6 C7 C8 C3 0.1(3) . . . . ?
C9 C7 C8 C3 -178.1(2) . . . . ?
C6 C7 C9 N3 137.5(3) . . . . ?
C8 C7 C9 N3 -44.3(3) . . . . ?
N4 C11 C12 O3 55.4(4) . . . . ?
O3 C13 C14 O4 77.4(3) . . . . ?
O4 C15 C16 N1 -74.7(4) . . . . ?
O1 C1 N1 C16 -1.6(4) . . . . ?
N2 C1 N1 C16 179.9(3) . . . . ?
C15 C16 N1 C1 -117.1(3) . . . . ?
O1 C1 N2 C2 17.5(4) . . . . ?
N1 C1 N2 C2 -164.0(2) . . . . ?
C3 C2 N2 C1 89.1(3) . . . . ?
O2 C10 N3 C9 -0.7(4) . . . . ?
N4 C10 N3 C9 178.9(2) . . . . ?
C7 C9 N3 C10 160.0(2) . . . . ?
O2 C10 N4 C11 -4.1(4) . . . . ?
N3 C10 N4 C11 176.4(3) . . . . ?
C12 C11 N4 C10 -173.0(3) . . . . ?
C14 C13 O3 C12 -179.7(2) . . . . ?
C11 C12 O3 C13 70.5(3) . . . . ?
C13 C14 O4 C15 -81.9(4) . . . . ?
C16 C15 O4 C14 -150.5(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658856
