#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/01/7050146.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_7050146
loop_
_publ_author_name
'Bond, Andrew D.'
_publ_section_title
;
 On the crystal structures and melting point alternation of the n-alkyl
 carboxylic acidsElectronic supplementary information (ESI) available:
 crystallographic data for C6?C15 in tabular and .cif format, full
 details of temperature calibration and density measurement, packing
 coefficients and lattice binding energies, formal definitions of the
 orthogonal cells, details of all projections and measurements of all
 geometric parameters referred to in the text. See
 http://www.rsc.org/suppdata/nj/b3/b307208h/
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              104
_journal_paper_doi               10.1039/b307208h
_journal_volume                  28
_journal_year                    2004
_chemical_formula_moiety         'C6 H12 O2'
_chemical_formula_sum            'C6 H12 O2'
_chemical_formula_weight         116.16
_chemical_melting_point          271
_chemical_name_common            'hexanoic acid'
_chemical_name_systematic        'hexanoic 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                 106.549(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0180(15)
_cell_length_b                   5.0236(5)
_cell_length_c                   9.9426(6)
_cell_measurement_reflns_used    4861
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.02
_cell_volume                     719.04(11)
_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      240(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4974
_diffrn_reflns_theta_full        24.95
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_min         4.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav Blessing (1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.073
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             256
_exptl_crystal_size_length       0.35
_exptl_crystal_size_rad          0.15
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         1233
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0504
_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)+(0.0639P)²+0.1124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1393
_reflns_number_gt                886
_reflns_number_total             1233
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b307208h.txt
_cod_data_source_block           C6
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7050146
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 0.48997(10) 0.7518(3) 0.61916(14) 0.0779(5) Uani 1 1 d D . .
H1 H 0.5264(13) 0.697(4) 0.570(2) 0.093 Uiso 1 1 d D . .
O2 O 0.40079(9) 0.4038(3) 0.53266(13) 0.0753(5) Uani 1 1 d . . .
C1 C 0.41891(12) 0.6006(4) 0.61010(17) 0.0613(5) Uani 1 1 d . . .
C2 C 0.36028(12) 0.6831(4) 0.70074(19) 0.0698(5) Uani 1 1 d . . .
H2A H 0.3377 0.8641 0.6742 0.084 Uiso 1 1 calc R . .
H2B H 0.3995 0.6897 0.7981 0.084 Uiso 1 1 calc R . .
C3 C 0.27810(13) 0.5085(4) 0.6950(2) 0.0720(6) Uani 1 1 d . . .
H3A H 0.2997 0.3247 0.7150 0.086 Uiso 1 1 calc R . .
H3B H 0.2358 0.5129 0.5996 0.086 Uiso 1 1 calc R . .
C4 C 0.22504(14) 0.5887(4) 0.7966(2) 0.0784(6) Uani 1 1 d . . .
H4A H 0.2674 0.5803 0.8919 0.094 Uiso 1 1 calc R . .
H4B H 0.2056 0.7746 0.7781 0.094 Uiso 1 1 calc R . .
C5 C 0.14229(17) 0.4274(6) 0.7922(3) 0.1066(9) Uani 1 1 d . . .
H5A H 0.1615 0.2410 0.8087 0.128 Uiso 1 1 calc R . .
H5B H 0.0993 0.4392 0.6975 0.128 Uiso 1 1 calc R . .
C6 C 0.09060(18) 0.5051(6) 0.8964(3) 0.1149(10) Uani 1 1 d . . .
H6A H 0.0380 0.3869 0.8863 0.172 Uiso 1 1 calc R . .
H6B H 0.0687 0.6870 0.8788 0.172 Uiso 1 1 calc R . .
H6C H 0.1319 0.4911 0.9909 0.172 Uiso 1 1 calc R . .
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 0.0836(10) 0.0729(9) 0.0874(10) -0.0202(7) 0.0408(7) -0.0105(7)
O2 0.0766(9) 0.0754(9) 0.0792(8) -0.0231(7) 0.0305(6) -0.0062(7)
C1 0.0652(11) 0.0590(10) 0.0598(10) -0.0007(8) 0.0180(8) 0.0072(9)
C2 0.0768(12) 0.0660(11) 0.0715(11) -0.0088(9) 0.0289(9) 0.0079(10)
C3 0.0727(12) 0.0696(12) 0.0785(12) -0.0084(9) 0.0290(9) 0.0076(9)
C4 0.0783(13) 0.0799(14) 0.0838(12) -0.0058(10) 0.0338(10) 0.0063(11)
C5 0.0966(17) 0.116(2) 0.1236(19) -0.0234(16) 0.0580(15) -0.0128(15)
C6 0.1009(18) 0.146(3) 0.1182(19) -0.0049(18) 0.0641(16) -0.0014(16)
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 114.4(15) . . ?
O2 C1 O1 123.03(16) . . ?
O2 C1 C2 122.51(17) . . ?
O1 C1 C2 114.46(16) . . ?
C1 C2 C3 115.86(16) . . ?
C1 C2 H2A 108.3 . . ?
C3 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
C3 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C2 C3 C4 113.79(16) . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 115.76(19) . . ?
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 115.5(2) . . ?
C4 C5 H5A 108.4 . . ?
C6 C5 H5A 108.4 . . ?
C4 C5 H5B 108.4 . . ?
C6 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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 1.292(2) . ?
O1 H1 0.88(2) . ?
O2 C1 1.235(2) . ?
C1 C2 1.487(2) . ?
C2 C3 1.502(3) . ?
C2 H2A 0.980 . ?
C2 H2B 0.980 . ?
C3 C4 1.509(3) . ?
C3 H3A 0.980 . ?
C3 H3B 0.980 . ?
C4 C5 1.474(3) . ?
C4 H4A 0.980 . ?
C4 H4B 0.980 . ?
C5 C6 1.512(3) . ?
C5 H5A 0.980 . ?
C5 H5B 0.980 . ?
C6 H6A 0.970 . ?
C6 H6B 0.970 . ?
C6 H6C 0.970 . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 1.2(3) . . . . ?
O1 C1 C2 C3 -178.81(15) . . . . ?
C1 C2 C3 C4 175.69(16) . . . . ?
C2 C3 C4 C5 178.44(19) . . . . ?
C3 C4 C5 C6 178.7(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8552
