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#$Date: 2025-01-07 17:02:22 +0200 (Tue, 07 Jan 2025) $
#$Revision: 297177 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/01/7050152.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_7050152
loop_
_publ_author_name
'Bond, Andrew D.'
_publ_section_title
;
 On the crystal structures and melting point alternation of the n-alkyl
 carboxylic acids
;
_journal_coden_ASTM              NJCHE5
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              104
_journal_page_last               114
_journal_paper_doi               10.1039/b307208h
_journal_volume                  28
_journal_year                    2004
_chemical_formula_moiety         'C12 H24 O2'
_chemical_formula_sum            'C12 H24 O2'
_chemical_formula_weight         200.31
_chemical_melting_point          317
_chemical_name_common            'dodecanoic acid'
_chemical_name_systematic        'dodecanoic acid'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.006(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.563(2)
_cell_length_b                   4.9627(3)
_cell_length_c                   9.5266(6)
_cell_measurement_reflns_used    58223
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      22.46
_cell_measurement_theta_min      1.02
_cell_volume                     1290.41(15)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor, 1997)
;
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      270(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0994
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5775
_diffrn_reflns_theta_full        22.45
_diffrn_reflns_theta_max         22.45
_diffrn_reflns_theta_min         4.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav Blessing (1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.031
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             448
_exptl_crystal_size_length       0.35
_exptl_crystal_size_rad          0.15
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1614
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0671
_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)+(0.0704P)²+0.4277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1813
_reflns_number_gt                1258
_reflns_number_total             1614
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b307208h.txt
_cod_data_source_block           C12
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7050152
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.05420(8) 0.6093(4) 0.9444(2) 0.0641(7) Uani 1 1 d D . .
H1 H 0.0329(15) 0.638(12) 0.996(5) 0.19(3) Uiso 1 1 d D . .
O2 O 0.00620(7) 0.2607(4) 0.8759(2) 0.0654(7) Uani 1 1 d . . .
C1 C 0.04368(10) 0.4083(6) 0.8667(3) 0.0508(8) Uani 1 1 d . . .
C2 C 0.07515(11) 0.3313(5) 0.7584(3) 0.0552(8) Uani 1 1 d . . .
H2A H 0.0551 0.3367 0.6662 0.066 Uiso 1 1 calc R . .
H2B H 0.0853 0.1458 0.7759 0.066 Uiso 1 1 calc R . .
C3 C 0.12048(11) 0.4982(5) 0.7501(3) 0.0572(8) Uani 1 1 d . . .
H3A H 0.1418 0.4873 0.8399 0.069 Uiso 1 1 calc R . .
H3B H 0.1111 0.6853 0.7342 0.069 Uiso 1 1 calc R . .
C4 C 0.14840(10) 0.4051(6) 0.6320(3) 0.0600(8) Uani 1 1 d . . .
H4A H 0.1547 0.2135 0.6438 0.072 Uiso 1 1 calc R . .
H4B H 0.1274 0.4294 0.5423 0.072 Uiso 1 1 calc R . .
C5 C 0.19623(11) 0.5442(6) 0.6232(3) 0.0630(9) Uani 1 1 d . . .
H5A H 0.2174 0.5211 0.7126 0.076 Uiso 1 1 calc R . .
H5B H 0.1902 0.7356 0.6096 0.076 Uiso 1 1 calc R . .
C6 C 0.22263(11) 0.4412(6) 0.5045(3) 0.0661(9) Uani 1 1 d . . .
H6A H 0.2265 0.2477 0.5151 0.079 Uiso 1 1 calc R . .
H6B H 0.2019 0.4737 0.4152 0.079 Uiso 1 1 calc R . .
C7 C 0.27226(12) 0.5626(6) 0.4961(3) 0.0698(9) Uani 1 1 d . . .
H7A H 0.2928 0.5342 0.5861 0.084 Uiso 1 1 calc R . .
H7B H 0.2684 0.7555 0.4825 0.084 Uiso 1 1 calc R . .
C8 C 0.29836(11) 0.4502(6) 0.3788(3) 0.0684(9) Uani 1 1 d . . .
H8A H 0.3014 0.2567 0.3913 0.082 Uiso 1 1 calc R . .
H8B H 0.2780 0.4821 0.2888 0.082 Uiso 1 1 calc R . .
C9 C 0.34844(12) 0.5648(7) 0.3707(4) 0.0749(10) Uani 1 1 d . . .
H9A H 0.3689 0.5332 0.4607 0.090 Uiso 1 1 calc R . .
H9B H 0.3454 0.7583 0.3578 0.090 Uiso 1 1 calc R . .
C10 C 0.37407(12) 0.4509(7) 0.2537(4) 0.0758(10) Uani 1 1 d . . .
H10A H 0.3766 0.2571 0.2657 0.091 Uiso 1 1 calc R . .
H10B H 0.3539 0.4852 0.1637 0.091 Uiso 1 1 calc R . .
C11 C 0.42436(14) 0.5624(8) 0.2474(4) 0.0936(12) Uani 1 1 d . . .
H11A H 0.4447 0.5255 0.3369 0.112 Uiso 1 1 calc R . .
H11B H 0.4219 0.7565 0.2368 0.112 Uiso 1 1 calc R . .
C12 C 0.44958(15) 0.4505(9) 0.1285(5) 0.1113(14) Uani 1 1 d . . .
H12A H 0.4812 0.5333 0.1310 0.167 Uiso 1 1 calc R . .
H12B H 0.4301 0.4881 0.0391 0.167 Uiso 1 1 calc R . .
H12C H 0.4535 0.2592 0.1399 0.167 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'
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
C1 O1 H1 111(4) . . ?
O1 C1 O2 122.6(2) . . ?
O1 C1 C2 120.4(3) . . ?
O2 C1 C2 117.1(2) . . ?
C1 C2 C3 117.5(2) . . ?
C1 C2 H2A 107.9 . . ?
C3 C2 H2A 107.9 . . ?
C1 C2 H2B 107.9 . . ?
C3 C2 H2B 107.9 . . ?
H2A C2 H2B 107.2 . . ?
C2 C3 C4 112.3(2) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 116.1(2) . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
C3 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C4 C5 C6 113.8(3) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C5 116.0(3) . . ?
C7 C6 H6A 108.3 . . ?
C5 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C5 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C6 C7 C8 114.8(3) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C7 115.5(3) . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 C10 115.0(3) . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C9 114.9(3) . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 C12 114.7(3) . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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 1.252(3) . ?
O1 H1 0.83(1) . ?
O2 C1 1.279(3) . ?
C1 C2 1.487(4) . ?
C2 C3 1.510(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.521(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.501(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.516(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.507(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.517(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.505(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.510(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.502(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.515(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3756
