#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/11/2221191.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2221191
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Chantrapromma, Suchada'
_publ_section_title
;
 A triclinic polymorph of hexanedioic acid
;
_journal_coeditor_code           SJ2583
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o624
_journal_paper_doi               10.1107/S1600536809006448
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H10 O4'
_chemical_formula_moiety         'C6 H10 O4'
_chemical_formula_sum            'C6 H10 O4'
_chemical_formula_weight         146.14
_chemical_name_common
;
Adipic acid
;
_chemical_name_systematic
;
hexanedioic acid
;
_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                93.794(4)
_cell_angle_beta                 104.321(4)
_cell_angle_gamma                102.689(4)
_cell_formula_units_Z            2
_cell_length_a                   6.7666(5)
_cell_length_b                   6.9992(5)
_cell_length_c                   7.7180(5)
_cell_measurement_reflns_used    1553
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.75
_cell_volume                     342.70(4)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7773
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.75
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_correction_T_min  0.8467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.202
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0402P)²+0.1411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0941
_reflns_number_gt                1419
_reflns_number_total             1553
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2583.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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_database_code               2221191
_cod_database_fobs_code          2221191
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1A 0.07345(14) 0.10624(13) 0.21778(12) 0.0182(2) Uani d . 1 . .
O O2A -0.11534(14) 0.20271(13) -0.02751(12) 0.0198(2) Uani d . 1 . .
H H2OA -0.0961 0.1042 -0.0779 0.030 Uiso calc R 1 . .
C C1A -0.02548(19) 0.22010(17) 0.14771(16) 0.0156(3) Uani d . 1 . .
C C2A -0.0623(2) 0.39330(18) 0.24950(16) 0.0174(3) Uani d . 1 . .
H H2AA -0.2127 0.3787 0.2269 0.021 Uiso calc R 1 . .
H H2AB -0.0057 0.5124 0.2026 0.021 Uiso calc R 1 . .
C C3A 0.03484(19) 0.41932(17) 0.45233(16) 0.0167(3) Uani d . 1 . .
H H3AA 0.1794 0.4448 0.4777 0.020 Uiso d R 1 . .
H H3AB -0.0108 0.3012 0.4996 0.020 Uiso d R 1 . .
O O1B 0.45905(14) 0.56597(12) 0.19844(12) 0.0189(2) Uani d . 1 . .
O O2B 0.61849(14) 0.75868(13) 0.02759(12) 0.0204(2) Uani d . 1 . .
H H2OB 0.5906 0.6539 -0.0380 0.031 Uiso calc R 1 . .
C C1B 0.54652(19) 0.72852(18) 0.17064(16) 0.0159(3) Uani d . 1 . .
C C2B 0.5885(2) 0.91565(18) 0.29479(16) 0.0173(3) Uani d . 1 . .
H H2BA 0.5457 1.0160 0.2236 0.021 Uiso calc R 1 . .
H H2BB 0.7389 0.9603 0.3491 0.021 Uiso calc R 1 . .
C C3B 0.47841(19) 0.89970(17) 0.44459(16) 0.0161(3) Uani d . 1 . .
H H3BA 0.5266 0.8106 0.5238 0.019 Uiso d R 1 . .
H H3BB 0.3356 0.8519 0.3947 0.019 Uiso d R 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1A 0.0225(5) 0.0180(4) 0.0144(4) 0.0084(4) 0.0033(3) -0.0012(3)
O2A 0.0287(5) 0.0185(4) 0.0129(4) 0.0113(4) 0.0033(4) -0.0023(3)
C1A 0.0165(6) 0.0157(6) 0.0135(6) 0.0019(4) 0.0049(4) -0.0014(4)
C2A 0.0218(6) 0.0156(6) 0.0151(6) 0.0066(5) 0.0044(5) -0.0013(5)
C3A 0.0192(6) 0.0155(6) 0.0149(6) 0.0050(5) 0.0039(5) -0.0021(5)
O1B 0.0248(5) 0.0160(4) 0.0166(4) 0.0050(4) 0.0078(4) -0.0008(3)
O2B 0.0278(5) 0.0164(4) 0.0173(5) 0.0022(4) 0.0111(4) -0.0034(3)
C1B 0.0157(6) 0.0177(6) 0.0140(6) 0.0056(5) 0.0028(4) -0.0009(5)
C2B 0.0204(6) 0.0149(6) 0.0156(6) 0.0029(5) 0.0055(5) -0.0028(5)
C3B 0.0185(6) 0.0150(6) 0.0138(6) 0.0034(5) 0.0039(5) -0.0019(5)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1A O2A H2OA . . 109.5 ?
O1A C1A O2A . . 123.52(11) ?
O1A C1A C2A . . 124.18(11) ?
O2A C1A C2A . . 112.29(10) ?
C1A C2A C3A . . 114.73(10) ?
C1A C2A H2AA . . 108.6 ?
C3A C2A H2AA . . 108.6 ?
C1A C2A H2AB . . 108.6 ?
C3A C2A H2AB . . 108.6 ?
H2AA C2A H2AB . . 107.6 ?
C2A C3A C3A . 2_566 111.19(13) ?
C2A C3A H3AA . . 110.2 ?
C3A C3A H3AA 2_566 . 111.6 ?
C2A C3A H3AB . . 109.9 ?
C3A C3A H3AB 2_566 . 106.7 ?
H3AA C3A H3AB . . 107.0 ?
C1B O2B H2OB . . 109.5 ?
O1B C1B O2B . . 123.41(11) ?
O1B C1B C2B . . 124.33(11) ?
O2B C1B C2B . . 112.25(10) ?
C1B C2B C3B . . 115.27(10) ?
C1B C2B H2BA . . 108.5 ?
C3B C2B H2BA . . 108.5 ?
C1B C2B H2BB . . 108.5 ?
C3B C2B H2BB . . 108.5 ?
H2BA C2B H2BB . . 107.5 ?
C2B C3B C3B . 2_676 110.83(12) ?
C2B C3B H3BA . . 110.6 ?
C3B C3B H3BA 2_676 . 108.1 ?
C2B C3B H3BB . . 109.3 ?
C3B C3B H3BB 2_676 . 109.7 ?
H3BA C3B H3BB . . 108.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C1A . 1.2199(15) ?
O2A C1A . 1.3237(14) ?
O2A H2OA . 0.8200 ?
C1A C2A . 1.5007(16) ?
C2A C3A . 1.5220(16) ?
C2A H2AA . 0.9700 ?
C2A H2AB . 0.9700 ?
C3A C3A 2_566 1.528(2) ?
C3A H3AA . 0.9222 ?
C3A H3AB . 0.9462 ?
O1B C1B . 1.2207(15) ?
O2B C1B . 1.3238(15) ?
O2B H2OB . 0.8200 ?
C1B C2B . 1.5001(16) ?
C2B C3B . 1.5201(17) ?
C2B H2BA . 0.9700 ?
C2B H2BB . 0.9700 ?
C3B C3B 2_676 1.525(2) ?
C3B H3BA . 0.9537 ?
C3B H3BB . 0.9224 ?
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
_geom_hbond_publ_flag
O2A H2OA O1A 2_555 0.82 1.82 2.6397(13) 172 y
O2B H2OB O1B 2_665 0.82 1.82 2.6421(13) 174 y
C2A H2AB O2A 2_565 0.97 2.58 3.5415(16) 171 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1A C1A C2A C3A . . . . 0.07(17) ?
O2A C1A C2A C3A . . . . 179.19(10) ?
C1A C2A C3A C3A . . . 2_566 -172.28(12) ?
O1B C1B C2B C3B . . . . -11.15(18) ?
O2B C1B C2B C3B . . . . 169.89(10) ?
C1B C2B C3B C3B . . . 2_676 -176.67(13) ?
