#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/26/7052666.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_7052666
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         'C14 H30 O2, 2(C H4 N2 O)'
_chemical_formula_sum            'C16 H38 N4 O4'
_chemical_formula_weight         350.50
_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                95.676(4)
_cell_angle_beta                 97.552(4)
_cell_angle_gamma                101.479(3)
_cell_formula_units_Z            1
_cell_length_a                   5.2049(3)
_cell_length_b                   7.4169(5)
_cell_length_c                   13.6376(9)
_cell_measurement_reflns_used    1458
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      3.38
_cell_volume                     507.21(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997'
_computing_molecular_graphics    'Ortep-99 for Windows (Farrugia, 1995)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir-92 (A. Altomare et al., 1992)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0863
_diffrn_reflns_av_sigmaI/netI    0.0791
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6171
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    0.082
_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             194
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .20
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0706
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0937P)²+0.0617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.1990
_reflns_number_gt                1458
_reflns_number_total             2294
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1nj20040b.txt
_cod_data_source_block           kdm0739
_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               7052666
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 0.2292(3) 0.19060(19) 0.95708(10) 0.0482(4) Uani 1 1 d . . .
O2 O -0.4239(3) 0.5891(2) 0.85793(10) 0.0504(4) Uani 1 1 d . . .
H2 H -0.3835 0.6472 0.9141 0.076 Uiso 1 1 calc R . .
C3 C -0.6076(4) 0.8102(3) 0.76319(14) 0.0426(5) Uani 1 1 d . . .
H3A H -0.6416 0.8702 0.8252 0.051 Uiso 1 1 calc R . .
H3B H -0.7660 0.7180 0.7341 0.051 Uiso 1 1 calc R . .
C7 C -0.9441(4) 1.3029(3) 0.58053(15) 0.0478(5) Uani 1 1 d . . .
H7A H -0.9784 1.3615 0.6429 0.057 Uiso 1 1 calc R . .
H7B H -1.1035 1.2124 0.5506 0.057 Uiso 1 1 calc R . .
C4 C -0.5533(4) 0.9541(3) 0.69238(15) 0.0459(5) Uani 1 1 d . . .
H4A H -0.3926 1.0446 0.7209 0.055 Uiso 1 1 calc R . .
H4B H -0.5226 0.8935 0.6300 0.055 Uiso 1 1 calc R . .
C2 C -0.3812(4) 0.7147(3) 0.78530(15) 0.0467(5) Uani 1 1 d . . .
H2A H -0.3564 0.6466 0.7240 0.056 Uiso 1 1 calc R . .
H2B H -0.2198 0.8076 0.8094 0.056 Uiso 1 1 calc R . .
C5 C -0.7776(4) 1.0547(3) 0.67088(15) 0.0467(5) Uani 1 1 d . . .
H5A H -0.9370 0.9647 0.6404 0.056 Uiso 1 1 calc R . .
H5B H -0.8122 1.1120 0.7335 0.056 Uiso 1 1 calc R . .
N1 N 0.0246(4) 0.3875(3) 0.87773(13) 0.0513(5) Uani 1 1 d . . .
H9A H 0.1715 0.4432 0.8617 0.062 Uiso 1 1 calc R . .
H9B H -0.1196 0.4237 0.8598 0.062 Uiso 1 1 calc R . .
C6 C -0.7202(4) 1.2026(3) 0.60286(15) 0.0498(6) Uani 1 1 d . . .
H6A H -0.6843 1.1454 0.5405 0.060 Uiso 1 1 calc R . .
H6B H -0.5613 1.2929 0.6336 0.060 Uiso 1 1 calc R . .
C8 C -0.8879(4) 1.4497(3) 0.51126(15) 0.0483(6) Uani 1 1 d . . .
H8A H -0.7285 1.5401 0.5412 0.058 Uiso 1 1 calc R . .
H8B H -0.8535 1.3911 0.4490 0.058 Uiso 1 1 calc R . .
N2 N -0.2099(3) 0.1629(3) 0.95434(12) 0.0503(5) Uani 1 1 d . . .
H10A H -0.2171 0.0712 0.9886 0.060 Uiso 1 1 calc R . .
H10B H -0.3516 0.2014 0.9356 0.060 Uiso 1 1 calc R . .
C1 C 0.0203(4) 0.2452(3) 0.93035(13) 0.0379(5) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0360(8) 0.0531(10) 0.0630(9) 0.0241(7) 0.0114(6) 0.0170(7)
O2 0.0542(9) 0.0478(9) 0.0554(8) 0.0243(7) 0.0071(7) 0.0184(7)
C3 0.0422(11) 0.0432(12) 0.0463(11) 0.0159(9) 0.0085(8) 0.0127(9)
C7 0.0513(12) 0.0469(13) 0.0519(12) 0.0191(9) 0.0105(10) 0.0185(10)
C4 0.0449(11) 0.0491(13) 0.0493(11) 0.0203(9) 0.0093(9) 0.0156(10)
C2 0.0469(12) 0.0474(13) 0.0536(11) 0.0219(9) 0.0124(9) 0.0181(10)
C5 0.0508(12) 0.0465(13) 0.0503(11) 0.0201(9) 0.0116(9) 0.0187(10)
N1 0.0472(10) 0.0511(11) 0.0650(11) 0.0271(9) 0.0129(8) 0.0204(9)
C6 0.0532(13) 0.0496(14) 0.0536(12) 0.0216(10) 0.0109(10) 0.0183(11)
C8 0.0515(13) 0.0482(13) 0.0521(11) 0.0210(10) 0.0100(9) 0.0186(11)
N2 0.0361(9) 0.0524(11) 0.0685(11) 0.0225(9) 0.0115(8) 0.0147(8)
C1 0.0367(10) 0.0385(11) 0.0409(10) 0.0063(8) 0.0056(8) 0.0131(8)
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
C2 C3 C4 112.83(16) . . ?
C6 C7 C8 113.91(18) . . ?
C5 C4 C3 113.53(17) . . ?
O2 C2 C3 112.81(16) . . ?
C6 C5 C4 113.60(17) . . ?
C5 C6 C7 113.90(18) . . ?
C8 C8 C7 114.0(2) 2_386 . ?
O1 C1 N2 120.80(18) . . ?
O1 C1 N1 120.78(18) . . ?
N2 C1 N1 118.42(17) . . ?
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 1.257(2) . ?
O2 C2 1.434(2) . ?
C3 C2 1.504(3) . ?
C3 C4 1.519(3) . ?
C7 C6 1.517(3) . ?
C7 C8 1.520(3) . ?
C4 C5 1.518(3) . ?
C5 C6 1.516(3) . ?
N1 C1 1.332(2) . ?
C8 C8 1.520(4) 2_386 ?
N2 C1 1.329(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139176006
