#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/48/4504832.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_4504832
loop_
_publ_author_name
'Thünemann, Andreas F'
'Kurth, Dirk G.'
'Beinhoff, Matthias'
'Bienert, Ralf'
'Schulz, Burkhard'
_publ_section_title
;
 V-shaped crystalline structures of di-n-alkyl esters of phosphoric acid.
;
_journal_issue                   13
_journal_name_full
'Langmuir : the ACS journal of surfaces and colloids'
_journal_page_first              5856
_journal_page_last               5861
_journal_paper_doi               10.1021/la0603572
_journal_volume                  22
_journal_year                    2006
_chemical_formula_sum            'C32 H67 O4 P'
_chemical_formula_weight         546.83
_chemical_name_common            'phosphoric acid dihexadecyl ester'
_space_group_IT_number           1
_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           SHELXTL
_cell_angle_alpha                85.242(12)
_cell_angle_beta                 86.283(11)
_cell_angle_gamma                77.441(10)
_cell_formula_units_Z            1
_cell_length_a                   4.717(3)
_cell_length_b                   5.602(3)
_cell_length_c                   33.609(19)
_cell_measurement_reflns_used    727
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.92
_cell_measurement_theta_min      3.04
_cell_volume                     862.9(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'PowderCell, PovRay'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  '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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            4569
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.22
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.354
_exptl_absorpt_correction_T_min  0.240
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_description       plate
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_coef       0.022(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         3853
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0693
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1024P)²+0.7451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1984
_refine_ls_wR_factor_ref         0.2029
_reflns_number_gt                3285
_reflns_number_total             3853
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            la0603572si20060317_055115.cif
_cod_data_source_block           dhp
_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_cell_volume        862.8(9)
_cod_original_sg_symbol_H-M      P1
_cod_database_code               4504832
loop_
_symmetry_equiv_pos_as_xyz
'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
P1 P 0.7180(3) 0.5647(2) 0.36202(6) 0.0319(3) Uani 1 1 d .
O1 O 0.6103(8) 0.7555(7) 0.32704(12) 0.0425(10) Uani 1 1 d .
O2 O 0.7852(7) 0.7051(6) 0.39744(13) 0.0411(10) Uani 1 1 d .
O3 O 0.4895(7) 0.4251(7) 0.37302(14) 0.0443(10) Uani 1 1 d .
O4 O 1.0120(8) 0.4069(7) 0.34938(14) 0.0494(12) Uani 1 1 d .
H4A H 1.1410 0.4449 0.3611 0.074 Uiso 1 1 calc R
C1 C 0.7904(12) 0.9101(11) 0.3065(2) 0.0450(14) Uani 1 1 d .
H1C H 0.9470 0.8119 0.2910 0.054 Uiso 1 1 calc R
H1D H 0.8751 0.9907 0.3257 0.054 Uiso 1 1 calc R
C2 C 0.6048(14) 1.0966(10) 0.27962(19) 0.0431(14) Uani 1 1 d .
H2C H 0.4596 1.2010 0.2959 0.052 Uiso 1 1 calc R
H2D H 0.5032 1.0128 0.2629 0.052 Uiso 1 1 calc R
C3 C 0.7687(12) 1.2557(11) 0.2531(2) 0.0441(14) Uani 1 1 d .
H3D H 0.9071 1.1529 0.2357 0.053 Uiso 1 1 calc R
H3E H 0.8775 1.3345 0.2695 0.053 Uiso 1 1 calc R
C4 C 0.5704(12) 1.4519(10) 0.22745(19) 0.0449(14) Uani 1 1 d .
H4D H 0.4527 1.3727 0.2124 0.054 Uiso 1 1 calc R
H4E H 0.4396 1.5593 0.2450 0.054 Uiso 1 1 calc R
C5 C 0.7268(12) 1.6069(11) 0.1984(2) 0.0448(14) Uani 1 1 d .
H5C H 0.8565 1.5006 0.1806 0.054 Uiso 1 1 calc R
H5D H 0.8446 1.6869 0.2133 0.054 Uiso 1 1 calc R
C6 C 0.5214(13) 1.8004(11) 0.1737(2) 0.0468(14) Uani 1 1 d .
H6C H 0.3937 1.9076 0.1916 0.056 Uiso 1 1 calc R
H6D H 0.4013 1.7200 0.1593 0.056 Uiso 1 1 calc R
C7 C 0.6738(12) 1.9552(11) 0.1439(2) 0.0483(15) Uani 1 1 d .
H7C H 0.7993 1.8484 0.1257 0.058 Uiso 1 1 calc R
H7D H 0.7960 2.0340 0.1582 0.058 Uiso 1 1 calc R
C8 C 0.4665(13) 2.1511(12) 0.1196(2) 0.0486(15) Uani 1 1 d .
H8C H 0.3449 2.0722 0.1052 0.058 Uiso 1 1 calc R
H8D H 0.3405 2.2574 0.1378 0.058 Uiso 1 1 calc R
C9 C 0.6181(13) 2.3068(12) 0.0899(2) 0.0523(15) Uani 1 1 d .
H9C H 0.7436 2.2005 0.0717 0.063 Uiso 1 1 calc R
H9D H 0.7404 2.3850 0.1044 0.063 Uiso 1 1 calc R
C10 C 0.4105(15) 2.5042(12) 0.0657(2) 0.0558(16) Uani 1 1 d .
H10C H 0.2862 2.4261 0.0516 0.067 Uiso 1 1 calc R
H10D H 0.2870 2.6119 0.0839 0.067 Uiso 1 1 calc R
C11 C 0.5610(16) 2.6579(13) 0.0355(2) 0.0589(18) Uani 1 1 d .
H11C H 0.6844 2.5501 0.0173 0.071 Uiso 1 1 calc R
H11D H 0.6856 2.7356 0.0496 0.071 Uiso 1 1 calc R
C12 C 0.3556(15) 2.8551(13) 0.0113(2) 0.0623(19) Uani 1 1 d .
H12C H 0.2288 2.7774 -0.0024 0.075 Uiso 1 1 calc R
H12D H 0.2343 2.9642 0.0295 0.075 Uiso 1 1 calc R
C13 C 0.5022(16) 3.0042(14) -0.0189(3) 0.067(2) Uani 1 1 d .
H13B H 0.6253 2.8946 -0.0368 0.081 Uiso 1 1 calc R
H13C H 0.6274 3.0829 -0.0051 0.081 Uiso 1 1 calc R
C14 C 0.2992(19) 3.2003(15) -0.0436(3) 0.073(2) Uani 1 1 d .
H14C H 0.1750 3.1226 -0.0578 0.088 Uiso 1 1 calc R
H14D H 0.1755 3.3107 -0.0258 0.088 Uiso 1 1 calc R
C15 C 0.455(2) 3.3452(18) -0.0731(3) 0.100(3) Uani 1 1 d .
H15A H 0.5811 3.2340 -0.0906 0.120 Uiso 1 1 calc R
H15B H 0.5782 3.4238 -0.0588 0.120 Uiso 1 1 calc R
C16 C 0.255(3) 3.5418(19) -0.0987(4) 0.120(4) Uani 1 1 d .
H16A H 0.3703 3.6270 -0.1170 0.180 Uiso 1 1 calc R
H16B H 0.1339 3.6561 -0.0817 0.180 Uiso 1 1 calc R
H16C H 0.1354 3.4658 -0.1134 0.180 Uiso 1 1 calc R
C17 C 0.5459(11) 0.8655(10) 0.41841(18) 0.0364(12) Uani 1 1 d .
H17C H 0.4145 0.7699 0.4318 0.044 Uiso 1 1 calc R
H17D H 0.4374 0.9860 0.3995 0.044 Uiso 1 1 calc R
C18 C 0.6712(12) 0.9902(10) 0.44819(19) 0.0394(14) Uani 1 1 d .
H18C H 0.8061 1.0811 0.4345 0.047 Uiso 1 1 calc R
H18D H 0.7797 0.8674 0.4667 0.047 Uiso 1 1 calc R
C19 C 0.4389(12) 1.1658(11) 0.47165(18) 0.0401(13) Uani 1 1 d .
H19A H 0.3282 1.2861 0.4530 0.048 Uiso 1 1 calc R
H19C H 0.3061 1.0739 0.4856 0.048 Uiso 1 1 calc R
C20 C 0.5605(12) 1.2984(11) 0.50159(19) 0.0448(14) Uani 1 1 d .
H20C H 0.6933 1.3900 0.4875 0.054 Uiso 1 1 calc R
H20D H 0.6720 1.1776 0.5201 0.054 Uiso 1 1 calc R
C21 C 0.3348(11) 1.4724(11) 0.52519(19) 0.0419(13) Uani 1 1 d .
H21C H 0.2243 1.5940 0.5067 0.050 Uiso 1 1 calc R
H21D H 0.2011 1.3810 0.5391 0.050 Uiso 1 1 calc R
C22 C 0.4568(12) 1.6029(11) 0.5553(2) 0.0475(15) Uani 1 1 d .
H22C H 0.5911 1.6938 0.5414 0.057 Uiso 1 1 calc R
H22D H 0.5668 1.4813 0.5739 0.057 Uiso 1 1 calc R
C23 C 0.2308(12) 1.7782(12) 0.5789(2) 0.0461(15) Uani 1 1 d .
H23C H 0.0963 1.6877 0.5928 0.055 Uiso 1 1 calc R
H23D H 0.1211 1.9004 0.5604 0.055 Uiso 1 1 calc R
C24 C 0.3571(12) 1.9075(11) 0.6090(2) 0.0498(15) Uani 1 1 d .
H24C H 0.4660 1.7852 0.6276 0.060 Uiso 1 1 calc R
H24D H 0.4924 1.9972 0.5951 0.060 Uiso 1 1 calc R
C25 C 0.1312(12) 2.0838(11) 0.6325(2) 0.0506(16) Uani 1 1 d .
H25B H -0.0042 1.9940 0.6463 0.061 Uiso 1 1 calc R
H25C H 0.0224 2.2060 0.6138 0.061 Uiso 1 1 calc R
C26 C 0.2559(13) 2.2138(12) 0.6627(2) 0.0538(17) Uani 1 1 d .
H26C H 0.3671 2.0916 0.6811 0.065 Uiso 1 1 calc R
H26D H 0.3890 2.3056 0.6487 0.065 Uiso 1 1 calc R
C27 C 0.0297(14) 2.3870(13) 0.6865(2) 0.0577(19) Uani 1 1 d .
H27C H -0.0800 2.5103 0.6681 0.069 Uiso 1 1 calc R
H27D H -0.1046 2.2956 0.7002 0.069 Uiso 1 1 calc R
C28 C 0.1545(15) 2.5142(13) 0.7169(2) 0.0632(19) Uani 1 1 d .
H28C H 0.2638 2.3910 0.7353 0.076 Uiso 1 1 calc R
H28D H 0.2893 2.6053 0.7032 0.076 Uiso 1 1 calc R
C29 C -0.0707(16) 2.6871(14) 0.7405(3) 0.070(2) Uani 1 1 d .
H29C H -0.2051 2.5958 0.7542 0.085 Uiso 1 1 calc R
H29D H -0.1804 2.8099 0.7221 0.085 Uiso 1 1 calc R
C30 C 0.0541(18) 2.8159(16) 0.7710(3) 0.077(3) Uani 1 1 d .
H30A H 0.1856 2.9099 0.7572 0.093 Uiso 1 1 calc R
H30B H 0.1665 2.6932 0.7892 0.093 Uiso 1 1 calc R
C31 C -0.176(2) 2.9871(19) 0.7952(3) 0.101(3) Uani 1 1 d .
H31A H -0.2936 3.1055 0.7769 0.121 Uiso 1 1 calc R
H31B H -0.3035 2.8917 0.8097 0.121 Uiso 1 1 calc R
C32 C -0.055(3) 3.124(2) 0.8248(4) 0.125(4) Uani 1 1 d .
H32A H -0.2121 3.2282 0.8388 0.188 Uiso 1 1 calc R
H32B H 0.0675 3.2230 0.8107 0.188 Uiso 1 1 calc R
H32C H 0.0569 3.0092 0.8436 0.188 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
O3 P1 O4 114.2(2)
O3 P1 O1 108.0(2)
O4 P1 O1 109.0(2)
O3 P1 O2 112.5(2)
O4 P1 O2 104.6(2)
O1 P1 O2 108.4(2)
C1 O1 P1 122.9(3)
C17 O2 P1 119.3(3)
O1 C1 C2 108.3(5)
C1 C2 C3 114.4(5)
C2 C3 C4 112.9(5)
C5 C4 C3 114.9(5)
C4 C5 C6 113.1(5)
C5 C6 C7 114.0(5)
C6 C7 C8 113.7(5)
C9 C8 C7 113.8(5)
C8 C9 C10 113.9(5)
C11 C10 C9 114.1(5)
C10 C11 C12 114.4(6)
C13 C12 C11 114.7(6)
C12 C13 C14 115.2(6)
C15 C14 C13 113.3(8)
C14 C15 C16 114.1(9)
O2 C17 C18 108.2(4)
C17 C18 C19 112.6(4)
C20 C19 C18 113.8(4)
C19 C20 C21 114.7(4)
C22 C21 C20 114.5(4)
C21 C22 C23 114.6(4)
C22 C23 C24 113.9(4)
C25 C24 C23 113.9(4)
C24 C25 C26 114.2(5)
C27 C26 C25 114.1(5)
C28 C27 C26 114.0(5)
C29 C28 C27 114.0(5)
C28 C29 C30 114.1(6)
C29 C30 C31 113.7(7)
C32 C31 C30 114.3(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O3 1.475(4)
P1 O4 1.529(4)
P1 O1 1.555(4)
P1 O2 1.565(4)
O1 C1 1.447(7)
O2 C17 1.463(6)
C1 C2 1.491(8)
C2 C3 1.506(8)
C3 C4 1.524(8)
C4 C5 1.515(8)
C5 C6 1.517(7)
C6 C7 1.519(8)
C7 C8 1.521(8)
C8 C9 1.516(9)
C9 C10 1.527(8)
C10 C11 1.516(10)
C11 C12 1.520(9)
C12 C13 1.490(11)
C13 C14 1.520(10)
C14 C15 1.488(12)
C15 C16 1.530(12)
C17 C18 1.487(7)
C18 C19 1.529(7)
C19 C20 1.508(7)
C20 C21 1.510(7)
C21 C22 1.507(7)
C22 C23 1.514(7)
C23 C24 1.515(7)
C24 C25 1.515(7)
C25 C26 1.515(8)
C26 C27 1.513(8)
C27 C28 1.510(9)
C28 C29 1.505(9)
C29 C30 1.518(10)
C30 C31 1.525(11)
C31 C32 1.517(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 67691
2 PubChem 75143
