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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/31/4503175.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_4503175
loop_
_publ_author_name
'Uno, Kenjiro'
'Ogawa, Yoshihiro'
'Nakamura, Naotake'
_publ_section_title
;
 Polymorphism of Long-Chain Alkane-α,ω-Diols with an Even Number of
 Carbon Atoms
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              592
_journal_paper_doi               10.1021/cg700729q
_journal_volume                  8
_journal_year                    2008
_chemical_formula_moiety         'C22 H46 O2'
_chemical_formula_sum            'C22 H46 O2'
_chemical_formula_weight         342.59
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_date             2007-07-24T06:33:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.21(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.691(4)
_cell_length_b                   5.235(3)
_cell_length_c                   43.416(6)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.50
_cell_measurement_theta_min      10.00
_cell_volume                     2193.5(16)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Rigaku AFC5R'
_diffrn_measurement_method       ω
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            2396
_diffrn_reflns_theta_full        70.59
_diffrn_reflns_theta_max         70.59
_diffrn_reflns_theta_min         4.09
_diffrn_standards_decay_%        3.37
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.477
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9132
_exptl_absorpt_correction_type   psi-scans
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.037
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2019
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0776P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1744
_reflns_number_gt                699
_reflns_number_total             2019
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg700729q-file002.cif
_cod_data_source_block           2_Docosane-1,22-diol-I'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4503175
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_calc_flag
_atom_site_refinement_flags
O1 O -0.2199(3) -0.1935(4) 0.23987(5) 0.0714(8) Uani 1 d D
H1 H -0.234(4) -0.339(4) 0.2463(9) 0.107 Uiso 1 d D
C1 C -0.1348(3) -0.2336(5) 0.21551(6) 0.0484(8) Uani 1 d .
H1A H -0.1833 -0.3389 0.1996 0.058 Uiso 1 calc R
H1B H -0.0509 -0.3224 0.2233 0.058 Uiso 1 calc R
C2 C -0.0983(3) 0.0169(6) 0.20201(6) 0.0479(8) Uani 1 d .
H2A H -0.0504 0.1208 0.2181 0.058 Uiso 1 calc R
H2B H -0.183 0.1052 0.1946 0.058 Uiso 1 calc R
C3 C -0.0081(3) -0.0094(6) 0.17566(6) 0.0460(8) Uani 1 d .
H3A H -0.0538 -0.1218 0.1602 0.055 Uiso 1 calc R
H3B H 0.0785 -0.0895 0.1834 0.055 Uiso 1 calc R
C4 C 0.0240(3) 0.2431(5) 0.16032(6) 0.0448(8) Uani 1 d .
H4A H -0.0625 0.3234 0.1526 0.054 Uiso 1 calc R
H4B H 0.0699 0.3556 0.1758 0.054 Uiso 1 calc R
C5 C 0.1149(3) 0.2141(5) 0.13381(6) 0.0439(8) Uani 1 d .
H5A H 0.2017 0.1355 0.1416 0.053 Uiso 1 calc R
H5B H 0.0694 0.0997 0.1185 0.053 Uiso 1 calc R
C6 C 0.1458(3) 0.4641(5) 0.11817(6) 0.0452(8) Uani 1 d .
H6A H 0.059 0.5418 0.1101 0.054 Uiso 1 calc R
H6B H 0.1904 0.5792 0.1335 0.054 Uiso 1 calc R
C7 C 0.2378(3) 0.4355(5) 0.09196(6) 0.0437(8) Uani 1 d .
H7A H 0.1936 0.3191 0.0767 0.052 Uiso 1 calc R
H7B H 0.3248 0.3589 0.1 0.052 Uiso 1 calc R
C8 C 0.2683(3) 0.6844(5) 0.07604(5) 0.0443(7) Uani 1 d .
H8A H 0.1813 0.7603 0.0678 0.053 Uiso 1 calc R
H8B H 0.3119 0.8012 0.0913 0.053 Uiso 1 calc R
C9 C 0.3611(3) 0.6562(5) 0.05001(6) 0.0448(8) Uani 1 d .
H9A H 0.3177 0.539 0.0348 0.054 Uiso 1 calc R
H9B H 0.4481 0.5807 0.0582 0.054 Uiso 1 calc R
C10 C 0.3915(3) 0.9047(5) 0.03399(6) 0.0454(8) Uani 1 d .
H10A H 0.3045 0.9799 0.0257 0.055 Uiso 1 calc R
H10B H 0.4346 1.0223 0.0492 0.055 Uiso 1 calc R
C11 C 0.4848(3) 0.8757(5) 0.00806(6) 0.0441(8) Uani 1 d .
H11A H 0.4418 0.7578 -0.0072 0.053 Uiso 1 calc R
H11B H 0.5719 0.8007 0.0164 0.053 Uiso 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 O1 H1 104(3) . .
O1 C1 C2 109.8(2) . .
O1 C1 H1A 109.7 . .
C2 C1 H1A 109.7 . .
O1 C1 H1B 109.7 . .
C2 C1 H1B 109.7 . .
H1A C1 H1B 108.2 . .
C1 C2 C3 113.1(3) . .
C1 C2 H2A 109 . .
C3 C2 H2A 109 . .
C1 C2 H2B 109 . .
C3 C2 H2B 109 . .
H2A C2 H2B 107.8 . .
C2 C3 C4 114.1(3) . .
C2 C3 H3A 108.7 . .
C4 C3 H3A 108.7 . .
C2 C3 H3B 108.7 . .
C4 C3 H3B 108.7 . .
H3A C3 H3B 107.6 . .
C5 C4 C3 113.6(2) . .
C5 C4 H4A 108.9 . .
C3 C4 H4A 108.9 . .
C5 C4 H4B 108.9 . .
C3 C4 H4B 108.9 . .
H4A C4 H4B 107.7 . .
C6 C5 C4 113.9(2) . .
C6 C5 H5A 108.8 . .
C4 C5 H5A 108.8 . .
C6 C5 H5B 108.8 . .
C4 C5 H5B 108.8 . .
H5A C5 H5B 107.7 . .
C7 C6 C5 113.9(2) . .
C7 C6 H6A 108.8 . .
C5 C6 H6A 108.8 . .
C7 C6 H6B 108.8 . .
C5 C6 H6B 108.8 . .
H6A C6 H6B 107.7 . .
C6 C7 C8 114.2(2) . .
C6 C7 H7A 108.7 . .
C8 C7 H7A 108.7 . .
C6 C7 H7B 108.7 . .
C8 C7 H7B 108.7 . .
H7A C7 H7B 107.6 . .
C9 C8 C7 114.2(2) . .
C9 C8 H8A 108.7 . .
C7 C8 H8A 108.7 . .
C9 C8 H8B 108.7 . .
C7 C8 H8B 108.7 . .
H8A C8 H8B 107.6 . .
C8 C9 C10 114.3(2) . .
C8 C9 H9A 108.7 . .
C10 C9 H9A 108.7 . .
C8 C9 H9B 108.7 . .
C10 C9 H9B 108.7 . .
H9A C9 H9B 107.6 . .
C11 C10 C9 114.1(2) . .
C11 C10 H10A 108.7 . .
C9 C10 H10A 108.7 . .
C11 C10 H10B 108.7 . .
C9 C10 H10B 108.7 . .
H10A C10 H10B 107.6 . .
C10 C11 C11 114.2(3) . 5_675
C10 C11 H11A 108.7 . .
C11 C11 H11A 108.7 5_675 .
C10 C11 H11B 108.7 . .
C11 C11 H11B 108.7 5_675 .
H11A C11 H11B 107.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.415(3) .
O1 H1 0.825(18) .
C1 C2 1.492(3) .
C1 H1A 0.97 .
C1 H1B 0.97 .
C2 C3 1.508(4) .
C2 H2A 0.97 .
C2 H2B 0.97 .
C3 C4 1.525(3) .
C3 H3A 0.97 .
C3 H3B 0.97 .
C4 C5 1.519(3) .
C4 H4A 0.97 .
C4 H4B 0.97 .
C5 C6 1.517(3) .
C5 H5A 0.97 .
C5 H5B 0.97 .
C6 C7 1.515(4) .
C6 H6A 0.97 .
C6 H6B 0.97 .
C7 C8 1.517(3) .
C7 H7A 0.97 .
C7 H7B 0.97 .
C8 C9 1.514(3) .
C8 H8A 0.97 .
C8 H8B 0.97 .
C9 C10 1.516(3) .
C9 H9A 0.97 .
C9 H9B 0.97 .
C10 C11 1.515(3) .
C10 H10A 0.97 .
C10 H10B 0.97 .
C11 C11 1.519(5) 5_675
C11 H11A 0.97 .
C11 H11B 0.97 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O1 4_445 0.825(18) 2.015(18) 2.8387(18) 176(4)
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_3
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 -179.6(2) . .
C1 C2 C3 C4 176.8(2) . .
C2 C3 C4 C5 -180.0(2) . .
C3 C4 C5 C6 179.3(2) . .
C4 C5 C6 C7 179.4(2) . .
C5 C6 C7 C8 179.6(2) . .
C6 C7 C8 C9 179.6(2) . .
C7 C8 C9 C10 179.9(2) . .
C8 C9 C10 C11 179.8(2) . .
C9 C10 C11 C11 179.9(2) . 5_675
C10 C11 C11 C10 -180.0(3) 5_675 5_675
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 347359
