#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/48/2204844.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_2204844
loop_
_publ_author_name
'Mondal, S.'
'Narasegowda, R. S.'
'Nagaraj, B.'
'Yathirajan, H. S.'
'Narasimhamurthy, T.'
'Rathore, Ravindranath S.'
_publ_section_title
;
 2,2'-Dipropylmalonic acid: intermolecular association via
 strong O---H···O hydrogen bonds
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o151
_journal_page_last               o153
_journal_paper_doi               10.1107/S1600536804033045
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C9 H16 O4'
_chemical_formula_moiety         'C9 H16 O4'
_chemical_formula_sum            'C9 H16 O4'
_chemical_formula_weight         188.22
_chemical_melting_point          432
_chemical_name_systematic
;
2,2'-Dipropylmalonic 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
_cell_angle_alpha                76.249(2)
_cell_angle_beta                 70.140(2)
_cell_angle_gamma                72.355(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6830(10)
_cell_length_b                   8.5490(10)
_cell_length_c                   9.3820(10)
_cell_measurement_reflns_used    3369
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55
_cell_measurement_theta_min      5
_cell_volume                     546.04(11)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics
'ORTEPIII (Farrugia, 1997) and PLUTON (Spek, 1999)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5840
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             204
_exptl_crystal_size_max          .55
_exptl_crystal_size_mid          .22
_exptl_crystal_size_min          .12
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0505
_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)+(0.0805P)²+0.0901P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1503
_reflns_number_gt                1784
_reflns_number_total             2261
_reflns_threshold_expression     I>2s(I)
_cod_data_source_file            bt6565.cif
_cod_data_source_block           I
_cod_original_cell_volume        546.05(12)
_cod_database_code               2204844
_cod_database_fobs_code          2204844
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
O1 0.0860(2) 0.07364(18) 0.79604(14) 0.0766(5) Uani d . 1 O
O2 -0.03567(18) 0.44811(19) 0.71039(15) 0.0784(5) Uani d . 1 O
O3 0.1097(2) 0.13697(17) 1.00235(13) 0.0745(4) Uani d . 1 O
O4 0.20931(16) 0.39020(17) 0.50464(12) 0.0706(4) Uani d . 1 O
C1 0.1404(2) 0.1565(2) 0.86526(17) 0.0512(4) Uani d . 1 C
C2 0.2539(2) 0.27809(19) 0.75464(16) 0.0491(4) Uani d . 1 C
C3 0.1413(2) 0.3764(2) 0.64235(17) 0.0538(4) Uani d . 1 C
C4 0.4476(2) 0.1756(2) 0.66546(17) 0.0533(4) Uani d . 1 C
H4A 0.4227 0.1063 0.6101 0.064 Uiso calc R 1 H
H4B 0.5164 0.2520 0.5901 0.064 Uiso calc R 1 H
C5 0.5761(3) 0.0656(2) 0.7608(2) 0.0655(5) Uani d . 1 C
H5A 0.6061 0.1335 0.8142 0.079 Uiso calc R 1 H
H5B 0.5093 -0.0116 0.8370 0.079 Uiso calc R 1 H
C6 0.7584(3) -0.0302(3) 0.6626(3) 0.0911(7) Uani d . 1 C
H6A 0.8364 -0.0989 0.7261 0.137 Uiso calc R 1 H
H6B 0.8259 0.0459 0.5884 0.137 Uiso calc R 1 H
H6C 0.7291 -0.0988 0.6107 0.137 Uiso calc R 1 H
C7 0.2733(2) 0.3985(2) 0.84349(18) 0.0576(4) Uani d . 1 C
H7A 0.1474 0.4486 0.9053 0.069 Uiso calc R 1 H
H7B 0.3481 0.3359 0.9127 0.069 Uiso calc R 1 H
C8 0.3661(4) 0.5356(3) 0.7421(3) 0.0910(7) Uani d . 1 C
H8A 0.4900 0.4855 0.6776 0.109 Uiso calc R 1 H
H8B 0.2887 0.6007 0.6755 0.109 Uiso calc R 1 H
C9 0.3916(5) 0.6487(3) 0.8279(3) 0.1129(9) Uani d . 1 C
H9A 0.4502 0.7321 0.7566 0.169 Uiso calc R 1 H
H9B 0.4715 0.5860 0.8918 0.169 Uiso calc R 1 H
H9C 0.2694 0.7009 0.8905 0.169 Uiso calc R 1 H
H1 0.026(4) 0.006(3) 0.856(3) 0.108(8) Uiso d . 1 H
H2 -0.094(4) 0.508(3) 0.642(3) 0.101(8) Uiso d . 1 H
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
O1 0.1062(11) 0.0927(10) 0.0492(7) -0.0677(9) -0.0236(7) 0.0136(6)
O2 0.0509(7) 0.1039(10) 0.0483(7) -0.0003(6) -0.0057(5) 0.0108(7)
O3 0.0966(10) 0.0984(10) 0.0427(7) -0.0646(8) -0.0189(6) 0.0148(6)
O4 0.0534(7) 0.0920(9) 0.0435(7) -0.0091(6) -0.0073(5) 0.0107(6)
C1 0.0504(8) 0.0590(9) 0.0436(8) -0.0238(7) -0.0150(7) 0.0091(6)
C2 0.0456(8) 0.0553(8) 0.0411(8) -0.0204(7) -0.0074(6) 0.0057(6)
C3 0.0475(8) 0.0579(9) 0.0445(8) -0.0185(7) -0.0054(6) 0.0089(6)
C4 0.0491(9) 0.0610(9) 0.0457(8) -0.0169(7) -0.0101(7) -0.0010(7)
C5 0.0606(10) 0.0743(11) 0.0641(11) -0.0102(8) -0.0250(8) -0.0127(9)
C6 0.0683(13) 0.1114(17) 0.0927(15) 0.0091(12) -0.0359(11) -0.0354(13)
C7 0.0573(9) 0.0600(10) 0.0492(9) -0.0237(8) -0.0031(7) -0.0028(7)
C8 0.1131(18) 0.0881(14) 0.0772(14) -0.0656(14) -0.0043(12) -0.0034(11)
C9 0.132(2) 0.0840(16) 0.124(2) -0.0580(16) -0.0058(17) -0.0237(15)
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
C1 O1 H1 113.2(18)
C3 O2 H2 110.4(17)
O3 C1 O1 123.73(14)
O3 C1 C2 123.18(14)
O1 C1 C2 113.06(13)
C3 C2 C1 107.15(12)
C3 C2 C7 109.01(13)
C1 C2 C7 109.91(12)
C3 C2 C4 109.01(12)
C1 C2 C4 107.97(13)
C7 C2 C4 113.58(13)
O4 C3 O2 123.42(15)
O4 C3 C2 123.45(14)
O2 C3 C2 113.11(13)
C5 C4 C2 116.08(13)
C5 C4 H4A 108.3
C2 C4 H4A 108.3
C5 C4 H4B 108.3
C2 C4 H4B 108.3
H4A C4 H4B 107.4
C6 C5 C4 111.42(16)
C6 C5 H5A 109.3
C4 C5 H5A 109.3
C6 C5 H5B 109.3
C4 C5 H5B 109.3
H5A C5 H5B 108.0
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
C8 C7 C2 114.01(14)
C8 C7 H7A 108.8
C2 C7 H7A 108.8
C8 C7 H7B 108.8
C2 C7 H7B 108.8
H7A C7 H7B 107.6
C9 C8 C7 114.15(19)
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 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.297(2)
O1 H1 0.83(3)
O2 C3 1.313(2)
O2 H2 0.88(3)
O3 C1 1.2056(18)
O4 C3 1.2093(18)
C1 C2 1.5297(19)
C2 C3 1.524(2)
C2 C7 1.537(2)
C2 C4 1.547(2)
C4 C5 1.515(2)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.506(3)
C5 H5A 0.9700
C5 H5B 0.9700
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 C8 1.517(2)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.487(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
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
O1 H1 O3 2_557 0.83(3) 1.85(3) 2.678(2) 176(3) y
O2 H2 O4 2_566 0.87(3) 1.80(3) 2.673(2) 175(3) 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
O3 C1 C2 C3 -133.23(17)
O1 C1 C2 C3 48.74(18)
O3 C1 C2 C7 -14.9(2)
O1 C1 C2 C7 167.06(14)
O3 C1 C2 C4 109.48(18)
O1 C1 C2 C4 -68.55(17)
C1 C2 C3 O4 -127.53(17)
C7 C2 C3 O4 113.56(18)
C4 C2 C3 O4 -10.9(2)
C1 C2 C3 O2 54.07(18)
C7 C2 C3 O2 -64.83(17)
C4 C2 C3 O2 170.68(14)
C3 C2 C4 C5 -178.15(14)
C1 C2 C4 C5 -62.07(18)
C7 C2 C4 C5 60.09(18)
C2 C4 C5 C6 178.96(16)
C3 C2 C7 C8 -56.9(2)
C1 C2 C7 C8 -174.03(17)
C4 C2 C7 C8 64.9(2)
C2 C7 C8 C9 -177.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 66828
