#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/26/7052667.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_7052667
loop_
_publ_author_name
'Martí-Rujas, Javier'
'Kariuki, Benson M.'
'Hughes, Colan E.'
'Morte-Ródenas, Anabel'
'Guo, Fang'
'Glavcheva-Laleva, Zornitza'
'Taştemür, Kemal'
'Ooi, Li-ling'
'Yeo, Lily'
'Harris, Kenneth D. M.'
_publ_section_title
;
 Structural diversity, but no polymorphism, in a homologous family of
 co-crystals of urea and α,ω-dihydroxyalkanes
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1515
_journal_paper_doi               10.1039/c1nj20040b
_journal_volume                  35
_journal_year                    2011
_chemical_formula_moiety         'C16 H34 O2, 2(C H4 N2 O)'
_chemical_formula_sum            'C18 H42 N4 O4'
_chemical_formula_weight         378.56
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.295(4)
_cell_angle_beta                 92.698(3)
_cell_angle_gamma                101.711(5)
_cell_formula_units_Z            1
_cell_length_a                   5.1973(5)
_cell_length_b                   7.3964(12)
_cell_length_c                   15.0141(16)
_cell_measurement_reflns_used    1615
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.30
_cell_measurement_theta_min      2.90
_cell_volume                     547.33(12)
_computing_cell_refinement       'MSC Software'
_computing_data_collection       'MSC Software'
_computing_data_reduction        'MSC Software'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SHELXS86
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.96
_diffrn_measured_fraction_theta_max 0.96
_diffrn_measurement_device_type  'Rigaku R-axis IIc Image plate'
_diffrn_measurement_method       'Image plate slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3090
_diffrn_reflns_theta_full        24.3
_diffrn_reflns_theta_max         24.30
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             210
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1860P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1650
_reflns_number_gt                1615
_reflns_number_total             1707
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1nj20040b.txt
_cod_data_source_block           diol16h
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7052667
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
O1 O -0.2641(3) 0.6812(2) 0.4609(1) 0.048(1) Uani 1 1 d . . .
O2 O 0.0982(3) 0.0575(2) 0.3705(1) 0.051(1) Uani 1 1 d . . .
N1 N -0.7031(3) 0.6528(3) 0.4584(1) 0.052(1) Uani 1 1 d . . .
N2 N -0.4577(3) 0.8597(3) 0.3874(1) 0.051(1) Uani 1 1 d . . .
C1 C -0.4685(4) 0.7298(3) 0.4362(1) 0.039(1) Uani 1 1 d . . .
C3 C -0.0711(4) 0.2554(3) 0.2830(1) 0.044(1) Uani 1 1 d . . .
C8 C -0.3136(4) 0.8390(3) 0.0523(2) 0.049(1) Uani 1 1 d . . .
C4 C -0.0063(4) 0.3835(3) 0.2178(1) 0.048(1) Uani 1 1 d . . .
C7 C -0.3794(4) 0.7079(3) 0.1156(1) 0.049(1) Uani 1 1 d . . .
C5 C -0.2260(4) 0.4793(3) 0.1982(1) 0.049(1) Uani 1 1 d . . .
C2 C 0.1513(4) 0.1656(3) 0.3034(1) 0.049(1) Uani 1 1 d . . .
C9 C -0.5334(4) 0.9346(3) 0.0319(1) 0.048(1) Uani 1 1 d . . .
C6 C -0.1591(4) 0.6125(3) 0.1361(2) 0.050(1) Uani 1 1 d . . .
H92 H -0.5726 1.0044 0.0880 0.075 Uiso 1 1 d . . .
H2 H 0.1447 0.1752 0.4400 0.075 Uiso 1 1 d . . .
H72 H -0.4293 0.7706 0.1738 0.075 Uiso 1 1 d . . .
H62 H 0.0122 0.7148 0.1674 0.075 Uiso 1 1 d . . .
H41 H 0.0282 0.3075 0.1568 0.075 Uiso 1 1 d . . .
H11 H -0.6035 0.8990 0.3772 0.075 Uiso 1 1 d . . .
H12 H -0.3028 0.9128 0.3797 0.075 Uiso 1 1 d . . .
H13 H -0.7120 0.5594 0.4901 0.075 Uiso 1 1 d . . .
H14 H -0.8452 0.6799 0.4422 0.075 Uiso 1 1 d . . .
H32 H -0.1221 0.3259 0.3363 0.075 Uiso 1 1 d . . .
H31 H -0.2318 0.1557 0.2595 0.075 Uiso 1 1 d . . .
H51 H -0.3810 0.3875 0.1695 0.075 Uiso 1 1 d . . .
H52 H -0.2788 0.5415 0.2535 0.075 Uiso 1 1 d . . .
H42 H 0.1526 0.4779 0.2422 0.075 Uiso 1 1 d . . .
H61 H -0.1042 0.5520 0.0767 0.075 Uiso 1 1 d . . .
H21 H 0.1856 0.0725 0.2479 0.075 Uiso 1 1 d . . .
H22 H 0.3175 0.2681 0.3209 0.075 Uiso 1 1 d . . .
H82 H -0.1386 0.9372 0.0791 0.075 Uiso 1 1 d . . .
H81 H -0.2596 0.7655 -0.0059 0.075 Uiso 1 1 d . . .
H71 H -0.5443 0.6099 0.0916 0.075 Uiso 1 1 d . . .
H91 H -0.7096 0.8254 0.0052 0.075 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'
O O 0.0106 0.0060 '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'
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 120.8(2) . . ?
O1 C1 N2 121.3(2) . . ?
N1 C1 N2 117.9(2) . . ?
C2 C3 C4 112.9(2) . . ?
C7 C8 C9 114.2(2) . . ?
C5 C4 C3 113.7(2) . . ?
C8 C7 C6 114.2(2) . . ?
C6 C5 C4 113.9(2) . . ?
O2 C2 C3 112.8(2) . . ?
C8 C9 C9 114.0(2) . 2_475 ?
C5 C6 C7 114.3(2) . . ?
C2 O2 H2 102.8 . . ?
C1 N1 H13 118.1 . . ?
C1 N1 H14 123.6 . . ?
H13 N1 H14 118.2 . . ?
C1 N2 H11 117.9 . . ?
C1 N2 H12 114.4 . . ?
H11 N2 H12 126.2 . . ?
C2 C3 H32 111.9 . . ?
C4 C3 H32 108.4 . . ?
C2 C3 H31 109.6 . . ?
C4 C3 H31 111.5 . . ?
H32 C3 H31 102.1 . . ?
C7 C8 H82 108.8 . . ?
C9 C8 H82 112.0 . . ?
C7 C8 H81 108.7 . . ?
C9 C8 H81 111.0 . . ?
H82 C8 H81 101.3 . . ?
C5 C4 H41 106.3 . . ?
C3 C4 H41 110.1 . . ?
C5 C4 H42 109.9 . . ?
C3 C4 H42 109.4 . . ?
H41 C4 H42 107.2 . . ?
C8 C7 H72 113.1 . . ?
C6 C7 H72 107.3 . . ?
C8 C7 H71 111.3 . . ?
C6 C7 H71 109.8 . . ?
H72 C7 H71 100.3 . . ?
C6 C5 H51 106.8 . . ?
C4 C5 H51 110.9 . . ?
C6 C5 H52 111.1 . . ?
C4 C5 H52 109.8 . . ?
H51 C5 H52 103.7 . . ?
O2 C2 H21 104.6 . . ?
C3 C2 H21 111.9 . . ?
O2 C2 H22 113.0 . . ?
C3 C2 H22 108.3 . . ?
H21 C2 H22 105.9 . . ?
C8 C9 H92 107.7 . . ?
C9 C9 H92 109.4 2_475 . ?
C8 C9 H91 108.4 . . ?
C9 C9 H91 111.6 2_475 . ?
H92 C9 H91 105.4 . . ?
C5 C6 H62 107.3 . . ?
C7 C6 H62 110.8 . . ?
C5 C6 H61 113.7 . . ?
C7 C6 H61 107.3 . . ?
H62 C6 H61 102.9 . . ?
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
O1 C1 1.255(2) . ?
O2 C2 1.427(2) . ?
N1 C1 1.329(2) . ?
N2 C1 1.330(2) . ?
C3 C2 1.498(3) . ?
C3 C4 1.516(3) . ?
C8 C7 1.510(3) . ?
C8 C9 1.514(3) . ?
C4 C5 1.512(3) . ?
C7 C6 1.516(3) . ?
C5 C6 1.509(3) . ?
C9 C9 1.514(4) 2_475 ?
O2 H2 1.174 . ?
N1 H13 0.919 . ?
N1 H14 0.843 . ?
N2 H11 0.884 . ?
N2 H12 0.847 . ?
C3 H32 0.931 . ?
C3 H31 0.984 . ?
C8 H82 1.039 . ?
C8 H81 1.002 . ?
C4 H41 1.003 . ?
C4 H42 0.961 . ?
C7 H72 0.964 . ?
C7 H71 0.994 . ?
C5 H51 0.952 . ?
C5 H52 0.934 . ?
C2 H21 0.999 . ?
C2 H22 1.006 . ?
C9 H92 0.937 . ?
C9 H91 1.081 . ?
C6 H62 1.053 . ?
C6 H61 0.985 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139176007
