A rapid and scalable method for visible light induced bromination of uracil derivatives in a falling film looping photoreactor
Naskar, Shibu; Mal, Susital; Shivangi, Shivangi; Das, Subrata; RSC Advances 14 (2024) 34925–34937; doi:10.1039/D4RA05774K

data_7249518
_publ_section_title
;
 A rapid and scalable method for visible light induced bromination of
 uracil derivatives in a falling film looping photoreactor
;
_journal_issue                   47
_journal_name_full               'RSC Advances'
_journal_page_first              34925
_journal_page_last               34937
_journal_paper_doi               10.1039/D4RA05774K
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C5 H4 Br Cl N2 O2'
_chemical_formula_sum            'C5 H4 Br Cl N2 O2'
_chemical_formula_weight         239.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-03 deposited with the CCDC.	2024-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.345(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9173(7)
_cell_length_b                   8.5748(4)
_cell_length_c                   8.1733(5)
_cell_measurement_reflns_used    5721
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      34.4860
_cell_measurement_theta_min      3.0630
_cell_volume                     721.93(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -60.37 142.63   0.50    1.00    --  -22.87  73.78-130.75  406
  2  \w    -60.37 142.63   0.50    1.00    --  -22.87  73.78 127.25  406
  3  \w    -60.37 142.63   0.50    1.00    --  -22.87  73.78  25.25  406
;
_diffrn_measurement_device       'Bruker diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0360289000
_diffrn_orient_matrix_UB_12      0.0403467000
_diffrn_orient_matrix_UB_13      0.0765715000
_diffrn_orient_matrix_UB_21      -0.0206587000
_diffrn_orient_matrix_UB_22      0.0721742000
_diffrn_orient_matrix_UB_23      -0.0426050000
_diffrn_orient_matrix_UB_31      -0.0549736000
_diffrn_orient_matrix_UB_32      -0.0006123000
_diffrn_orient_matrix_UB_33      0.0279460000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7469
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.339
_diffrn_reflns_theta_min         3.091
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.007
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.203
_exptl_crystal_description       prism
_exptl_crystal_F_000             464.000
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.911
_refine_diff_density_min         -1.903
_refine_diff_density_rms         0.224
_refine_ls_extinction_coef       0.082(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0695P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1261
_reflns_number_total             1319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra05774k2.cif
_cod_data_source_block           20jula_chabs2
_cod_database_code               7249518
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C5 H4 Br1 N2 O2 Cl1'
_shelx_estimated_absorpt_t_max   0.761
_shelx_estimated_absorpt_t_min   0.450
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_shelx_res_checksum              57240
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 15.793
_oxdiff_exptl_absorpt_empirical_full_min 0.460