Optimisation of aqueous solubility in a series of G protein coupled receptor 119 (GPR119) agonists
Scott, James S.; Birch, Alan M.; Brocklehurst, Katy J.; Brown, Hayley S.; Goldberg, Kristin; Groombridge, Sam D.; Hudson, Julian A.; Leach, Andrew G.; MacFaul, Philip A.; McKerrecher, Darren; Poultney, Ruth; Schofield, Paul; Svensson, Per H.; MedChemComm 4 (2013) 95–; doi:10.1039/c2md20130e

data_7112513
_publ_section_title
;
 Optimisation of aqueous solubility in a series of G protein coupled
 receptor 119 (GPR119) agonists
;
_journal_issue                   1
_journal_name_full               MedChemComm
_journal_page_first              95
_journal_paper_doi               10.1039/c2md20130e
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C20 H22 N6 O4'
_chemical_formula_sum            'C20 H22 N6 O4'
_chemical_formula_weight         410.44
_chemical_name_systematic
;
tetrahydrofuran-3-yl 4-(5-((3-cyanopyridin-4-yl)
methoxy)pyrimidin-2-yl)piperazine-1-carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        '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                85.165(6)
_cell_angle_beta                 83.895(6)
_cell_angle_gamma                76.853(5)
_cell_formula_units_Z            2
_cell_length_a                   5.2885(7)
_cell_length_b                   11.2227(15)
_cell_length_c                   16.881(2)
_cell_measurement_reflns_used    5121
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.43
_cell_volume                     968.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15781
_diffrn_reflns_theta_full        25.1
_diffrn_reflns_theta_max         25.1
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker Kappa APEXII'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0549
_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/[\s^2^(Fo^2^)+(0.0668P)^2^+0.9645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1478
_reflns_number_gt                1917
_reflns_number_total             3457
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2md20130e.txt
_cod_data_source_block           13
_cod_depositor_comments
;
 Updating space group information.

 Antanas Vaitkus,
 2018-06-07

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'N/A' 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 
;
_cod_original_cell_volume        968.3(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7112513