#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:04:14 +0100 (mar 22 de mar de 2016) $
#$Revision: 178932 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/61/4116151.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_4116151
loop_
_publ_author_name
'Venkat R. Thalladi'
'Markus Nüsse'
'Roland Boese'
_publ_section_title
;
 The Melting Point Alternation in α,ω-Alkanedicarboxylic Acids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9227
_journal_page_last               9236
_journal_paper_doi               10.1021/ja0011459
_journal_volume                  122
_journal_year                    2000
_chemical_compound_source        Fluka
_chemical_formula_moiety         'C5 H8 O4'
_chemical_formula_structural     'C5 H8 O4'
_chemical_formula_sum            'C5 H8 O4'
_chemical_formula_weight         132.12
_chemical_melting_point          372
_chemical_name_common            'Glutaric acid'
_chemical_name_systematic
; 
 Pentane-1,5-dioic acid 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 96.872(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.968(3)
_cell_length_b                   4.8296(12)
_cell_length_c                   9.982(2)
_cell_measurement_temperature    298(2)
_cell_volume                     620.7(2)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_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  0.0064
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            535
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    0.124
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             280
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.046
_refine_ls_goodness_of_fit_obs   1.109
_refine_ls_matrix_type           full
_refine_ls_number_parameters     50
_refine_ls_number_reflns         393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_restrained_S_obs      1.109
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_obs          0.0415
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0886P)²+0.2268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1267
_refine_ls_wR_factor_obs         0.1196
_reflns_number_observed          321
_reflns_number_total             393
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja0011459_13.cif
_cod_data_source_block           disa50m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'mpnoclinic' was replaced with
'monoclinic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0886P)^2^+0.2268P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0886P)^2^+0.2268P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        620.7(3)
_cod_database_code               4116151
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_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 0.0595(11) 0.0683(13) 0.0808(15) 0.0143(9) 0.0305(9) 0.0090(7)
O2 0.0535(10) 0.0709(12) 0.077(2) 0.0072(8) 0.0291(8) 0.0090(8)
C1 0.0471(12) 0.0543(14) 0.055(2) -0.0057(10) 0.0148(9) 0.0024(9)
C2 0.0547(13) 0.0592(14) 0.069(2) 0.0074(10) 0.0260(12) 0.0044(10)
C3 0.053(2) 0.057(2) 0.063(3) 0.000 0.023(2) 0.000
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.36727(12) -0.3034(3) 0.9480(2) 0.0678(7) Uani 1 d .
O2 O 0.25671(11) 0.0402(4) 0.8895(2) 0.0655(7) Uani 1 d .
H1 H 0.2123(29) -0.0558(81) 0.9542(38) 0.130(12) Uiso 1 d .
C1 C 0.3452(2) -0.0876(5) 0.8858(2) 0.0515(7) Uani 1 d .
C2 C 0.4192(2) 0.0574(5) 0.8063(2) 0.0596(8) Uani 1 d .
H2A H 0.4552(2) 0.1982(5) 0.8633(2) 0.072 Uiso 1 calc R
H2B H 0.3792(2) 0.1518(5) 0.7315(2) 0.072 Uiso 1 calc R
C3 C 0.5000 -0.1221(7) 0.7500 0.0559(9) Uani 1 d S
H3A H 0.5332(21) -0.2373(49) 0.8223(26) 0.068(7) Uiso 1 d .
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
O1 C1 O2 122.6(2) .
O1 C1 C2 122.8(2) .
O2 C1 C2 114.6(2) .
C1 C2 C3 116.4(2) .
C2 C3 C2 110.4(3) 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.230(3) .
O2 C1 1.307(2) .
C1 C2 1.491(3) .
C2 C3 1.519(3) .
C3 C2 1.519(3) 2_656
