#------------------------------------------------------------------------------
#$Date: 2024-11-02 04:03:44 +0200 (Sat, 02 Nov 2024) $
#$Revision: 295725 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/95/7249517.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249517
loop_
_publ_author_name
'Naskar, Shibu'
'Mal, Susital'
'Shivangi, Shivangi'
'Das, Subrata'
_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         'C7 H8 Br Cl N2 O2'
_chemical_formula_sum            'C7 H8 Br Cl N2 O2'
_chemical_formula_weight         267.51
_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             2024-08-23
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-08-27 deposited with the CCDC.	2024-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.765(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.6708(5)
_cell_length_b                   15.1340(10)
_cell_length_c                   13.5776(8)
_cell_measurement_reflns_used    1574
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0430
_cell_measurement_theta_min      3.0850
_cell_volume                     958.65(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0303
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  33.00   1.00   18.00    --   14.69  77.00  90.00   45
  2  ω     -9.00  54.00   1.00   18.00    --   14.69 -99.00 -30.00   63
  3  ω    -22.00  36.00   1.00   18.00    --  -16.64  19.00 150.00   58
  4  ω    -65.00  -2.00   1.00   18.00    --  -16.64 -57.00 -30.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0195026000
_diffrn_orient_matrix_UB_12      0.0463269000
_diffrn_orient_matrix_UB_13      0.0042654000
_diffrn_orient_matrix_UB_21      0.1502457000
_diffrn_orient_matrix_UB_22      -0.0056858000
_diffrn_orient_matrix_UB_23      -0.0019716000
_diffrn_orient_matrix_UB_31      -0.0114508000
_diffrn_orient_matrix_UB_32      0.0039796000
_diffrn_orient_matrix_UB_33      -0.0521507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4077
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.016
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol-Water'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1759
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0465P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1241
_reflns_number_total             1759
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra05774k2.cif
_cod_data_source_block           cb_61_b
_cod_database_code               7249517
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Br Cl'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.148
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
1.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C5(H5A,H5B,H5C)
;
_olex2_date_sample_data_collection 1979-12-31
_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 3.892
_oxdiff_exptl_absorpt_empirical_full_min 0.530
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.33104(13) 0.19914(4) 0.83116(4) 0.0466(2) Uani 1 1 d . . . . .
Cl1 Cl 0.7025(3) 0.07079(9) 0.69460(10) 0.0466(4) Uani 1 1 d . . . . .
O1 O 0.3933(8) 0.3846(2) 0.7481(2) 0.0485(10) Uani 1 1 d . . . . .
O2 O 1.0467(8) 0.3306(2) 0.5191(3) 0.0526(11) Uani 1 1 d . . . . .
N1 N 0.8737(9) 0.2127(2) 0.6013(3) 0.0323(10) Uani 1 1 d . . . . .
N2 N 0.7214(9) 0.3573(3) 0.6334(3) 0.0324(10) Uani 1 1 d . . . . .
C1 C 0.5455(10) 0.2375(3) 0.7266(3) 0.0277(11) Uani 1 1 d . . . . .
C2 C 0.5402(11) 0.3311(3) 0.7062(3) 0.0343(12) Uani 1 1 d . . . . .
C4 C 0.7045(10) 0.1828(3) 0.6742(3) 0.0290(12) Uani 1 1 d . . . . .
C3 C 0.8925(11) 0.3020(3) 0.5798(3) 0.0334(12) Uani 1 1 d . . . . .
C6 C 1.0417(11) 0.1532(3) 0.5390(3) 0.0391(13) Uani 1 1 d . . . . .
H6A H 1.113310 0.104009 0.578766 0.047 Uiso 1 1 calc R U . . .
H6B H 1.205655 0.185286 0.516143 0.047 Uiso 1 1 calc R U . . .
C7 C 0.8692(13) 0.1182(4) 0.4517(4) 0.0582(17) Uani 1 1 d . . . . .
H7A H 0.991799 0.085307 0.410315 0.087 Uiso 1 1 calc R U . . .
H7B H 0.784677 0.166556 0.414924 0.087 Uiso 1 1 calc R U . . .
H7C H 0.720666 0.080240 0.473785 0.087 Uiso 1 1 calc R U . . .
C5 C 0.7389(12) 0.4527(3) 0.6117(4) 0.0587(18) Uani 1 1 d . . . . .
H5A H 0.558368 0.480125 0.623292 0.088 Uiso 1 1 calc R U . . .
H5B H 0.783399 0.460825 0.544023 0.088 Uiso 1 1 calc R U . . .
H5C H 0.886396 0.479030 0.653745 0.088 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C3 121.2(4) . . ?
C4 N1 C6 123.3(4) . . ?
C3 N1 C6 115.5(4) . . ?
C2 N2 C5 117.5(4) . . ?
C3 N2 C2 125.9(4) . . ?
C3 N2 C5 116.6(4) . . ?
C2 C1 Br1 116.5(4) . . ?
C4 C1 Br1 122.9(4) . . ?
C4 C1 C2 120.6(4) . . ?
O1 C2 N2 121.2(5) . . ?
O1 C2 C1 124.5(5) . . ?
N2 C2 C1 114.3(4) . . ?
N1 C4 Cl1 116.7(4) . . ?
C1 C4 Cl1 121.1(4) . . ?
C1 C4 N1 122.2(4) . . ?
O2 C3 N1 122.9(5) . . ?
O2 C3 N2 121.4(5) . . ?
N1 C3 N2 115.7(4) . . ?
N1 C6 H6A 109.0 . . ?
N1 C6 H6B 109.0 . . ?
N1 C6 C7 112.7(4) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.869(4) . ?
Cl1 C4 1.718(5) . ?
O1 C2 1.219(6) . ?
O2 C3 1.201(6) . ?
N1 C4 1.373(5) . ?
N1 C3 1.386(6) . ?
N1 C6 1.485(6) . ?
N2 C2 1.390(6) . ?
N2 C3 1.388(6) . ?
N2 C5 1.475(6) . ?
C1 C2 1.443(7) . ?
C1 C4 1.340(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.498(7) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 O1 -4.7(7) . . . . ?
Br1 C1 C2 N2 174.9(3) . . . . ?
Br1 C1 C4 Cl1 4.5(6) . . . . ?
Br1 C1 C4 N1 -176.2(3) . . . . ?
C2 N2 C3 O2 -178.8(5) . . . . ?
C2 N2 C3 N1 1.0(7) . . . . ?
C2 C1 C4 Cl1 -177.5(3) . . . . ?
C2 C1 C4 N1 1.7(7) . . . . ?
C4 N1 C3 O2 177.1(5) . . . . ?
C4 N1 C3 N2 -2.7(7) . . . . ?
C4 N1 C6 C7 85.2(6) . . . . ?
C4 C1 C2 O1 177.2(5) . . . . ?
C4 C1 C2 N2 -3.2(7) . . . . ?
C3 N1 C4 Cl1 -179.3(4) . . . . ?
C3 N1 C4 C1 1.4(7) . . . . ?
C3 N1 C6 C7 -93.4(5) . . . . ?
C3 N2 C2 O1 -178.5(5) . . . . ?
C3 N2 C2 C1 1.8(7) . . . . ?
C6 N1 C4 Cl1 2.2(6) . . . . ?
C6 N1 C4 C1 -177.2(4) . . . . ?
C6 N1 C3 O2 -4.3(7) . . . . ?
C6 N1 C3 N2 176.0(4) . . . . ?
C5 N2 C2 O1 2.6(7) . . . . ?
C5 N2 C2 C1 -177.0(4) . . . . ?
C5 N2 C3 O2 0.1(7) . . . . ?
C5 N2 C3 N1 179.9(4) . . . . ?
