Theobromine and direct arylation: a sustainable and scalable solution to minimize aggregation caused quenching
Huang, Yunping; Liu, Yun; Sommerville, Parker J. W.; Kaminsky, Werner; Ginger, David S.; Luscombe, Christine K.; Green Chemistry  (2019) –; doi:10.1039/C9GC03391B

data_7238049
_publ_section_title
;
 Theobromine and direct arylation: a sustainable and scalable solution to
 minimize aggregation caused quenching
;
_journal_name_full               'Green Chemistry'
_journal_paper_doi               10.1039/C9GC03391B
_journal_year                    2019
_chemical_formula_moiety         'C31 H32 N4 O2'
_chemical_formula_sum            'C31 H32 N4 O2'
_chemical_formula_weight         492.6
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2018-07-10T11:42:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-11-01 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.508(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.6000(16)
_cell_length_b                   12.9539(10)
_cell_length_c                   8.9450(6)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.46
_cell_measurement_wavelength     0.71073
_cell_volume                     2502.8(3)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      -0.034195
_diffrn_orient_matrix_UB_12      -0.051006
_diffrn_orient_matrix_UB_13      -0.031861
_diffrn_orient_matrix_UB_21      -0.018782
_diffrn_orient_matrix_UB_22      -0.051818
_diffrn_orient_matrix_UB_23      0.033355
_diffrn_orient_matrix_UB_31      -0.10477
_diffrn_orient_matrix_UB_32      0.025936
_diffrn_orient_matrix_UB_33      0.003981
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12181
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.343
_diffrn_reflns_theta_min         1.833
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0023(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     338
_refine_ls_number_reflns         6225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.9464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0
_reflns_number_gt                4499
_reflns_number_total             6225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc03391b2.cif
_cod_data_source_block           shelx_CCDC1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7238049
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              30306
_shelx_hkl_checksum              31446