(<i>E</i>)-8-(3-Chlorostyryl)-1,3,7-trimethylxanthine, a caffeine derivative acting both as antagonist of adenosine A2A receptors and as inhibitor of MAO-B
Frédérick, Raphaël; Ooms, Frederic; Castagnoli Jr, Neal; Petzer, Jacques P.; Feng, Jiang-Fan; Schwarzschild, Michael A.; Van der Schyf, Cornelis J.; Wouters, Johan; Acta Crystallographica Section C 61 (2005) o531–o532; doi:10.1107/S0108270105023140

data_2015004
_publ_section_title
;
 (<i>E</i>)-8-(3-Chlorostyryl)-1,3,7-trimethylxanthine, a caffeine
 derivative acting both as antagonist of adenosine A2A receptors and as
 inhibitor of MAO-B
;
_journal_coeditor_code           GD1409
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o531
_journal_page_last               o532
_journal_paper_doi               10.1107/S0108270105023140
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H15 Cl N4 O2'
_chemical_formula_moiety         'C16 H15 Cl N4 O2'
_chemical_formula_sum            'C16 H15 Cl N4 O2'
_chemical_formula_weight         330.77
_chemical_name_common
;
(E)-8-(3-Chlorostyryl)-1,3,7-trimethylxanthine
;
_chemical_name_systematic
;
(E)-8-(3-chlorostyryl)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
;
_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                77.864(7)
_cell_angle_beta                 77.502(6)
_cell_angle_gamma                66.214(5)
_cell_formula_units_Z            2
_cell_length_a                   8.2440(10)
_cell_length_b                   8.3190(10)
_cell_length_c                   12.7220(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      45
_cell_measurement_theta_min      4
_cell_volume                     772.05(15)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2001)'
_computing_publication_material  'PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54175
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3240
_diffrn_reflns_theta_full        71.83
_diffrn_reflns_theta_max         71.83
_diffrn_reflns_theta_min         3.59
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.328
_exptl_absorpt_correction_T_max  0.8005
_exptl_absorpt_correction_T_min  0.5229
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(de Meulenaer & Tompa, 1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         .326
_refine_diff_density_min         -.398
_refine_ls_extinction_coef       0.0124(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[\s^2^(Fo^2^)+(0.0756P)^2^+0.2615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                2776
_reflns_number_total             3015
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd1409.cif
_cod_data_source_block           I
_cod_database_code               2015004