Conformation of cis,trans-1,3,5-trimethylcyclohexane-1,3,5-tricarboxylic acid derivatives: crystal structures and semiempirical molecular orbital calculations
Thuéry, Pierre; Nierlich, Martine; Baldwin, Bruce W.; Aoki, Yoshio; Hirose, Takuji; Journal of the Chemical Society, Perkin Transactions 2  (1999) 2077–; doi:10.1039/a904475b

data_7213124
_publ_section_title
;
 Conformation of cis,trans-1,3,5-trimethylcyclohexane-1,3,5-tricarboxylic
 acid derivatives: crystal structures and semiempirical molecular orbital
 calculations
;
_journal_issue                   10
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              2077
_journal_paper_doi               10.1039/a904475b
_journal_year                    1999
_chemical_formula_sum            'C23 H32 O6'
_chemical_formula_weight         404.49
_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
_cell_angle_alpha                84.929(3)
_cell_angle_beta                 72.592(3)
_cell_angle_gamma                89.799(3)
_cell_formula_units_Z            8
_cell_length_a                   12.6745(7)
_cell_length_b                   18.0319(11)
_cell_length_c                   19.9940(11)
_cell_measurement_reflns_used    32811
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.99
_cell_measurement_theta_min      2.63
_cell_volume                     4341.9(4)
_computing_cell_refinement       'HKL package (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa-CCD software (Nonius, 1997)'
_computing_data_reduction        'HKL package (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measurement_device       'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector'
_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  0.082
_diffrn_reflns_av_sigmaI/netI    0.072
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32811
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.63
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0163(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.091
_refine_ls_goodness_of_fit_obs   1.162
_refine_ls_hydrogen_treatment    'see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1045
_refine_ls_number_reflns         16960
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.080
_refine_ls_restrained_S_obs      1.163
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_obs          0.1134
_refine_ls_shift/esd_max         -0.007
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0169P)^2^+33.9531P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.3113
_refine_ls_wR_factor_obs         0.2590
_reflns_number_observed          9735
_reflns_number_total             16960
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            904475bsup1.cif
_cod_data_source_block           1b
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0169P)^2^+33.9531P] 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^)+(0.0169P)^2^+33.9531P] 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        4342(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7213124