Synthetic studies towards xanthomonadin.
Hsieh, Min-Tsang; Lin, Hui-Chang; Organic & biomolecular chemistry 23 (2025) 5234–5239; doi:10.1039/d5ob00518c

data_7160537
_publ_section_title
;
 Synthetic studies towards xanthomonadin.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5234
_journal_page_last               5239
_journal_paper_doi               10.1039/d5ob00518c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C18 H18 Br2 O3'
_chemical_formula_sum            'C18 H18 Br2 O3'
_chemical_formula_weight         442.14
_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     dual
_audit_creation_date             2024-02-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-20 deposited with the CCDC.	2025-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                83.716(4)
_cell_angle_beta                 83.816(4)
_cell_angle_gamma                87.352(4)
_cell_formula_units_Z            2
_cell_length_a                   6.4686(3)
_cell_length_b                   9.6305(5)
_cell_length_c                   14.1364(6)
_cell_measurement_reflns_used    5739
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.8880
_cell_measurement_theta_min      3.1210
_cell_volume                     869.73(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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    -98.00 -38.00   0.50    0.05    --  -81.00 118.00 143.70  120
  2  \w    -46.00 -19.00   0.50    0.05    --  -59.02 125.00 -30.00   54
  3  \w    -64.00 -26.00   0.50    0.05    --  -71.52 125.00 -60.00   76
  4  \w    -60.00 -26.00   0.50    0.05    --  -71.52 125.00-150.00   68
  5  \w    -98.00 -72.00   0.50    0.05    --  -71.52 125.00-150.00   52
  6  \w    -97.00 -35.00   0.50    0.05    --  -81.00 114.00   9.35  124
  7  \w    -72.00 -33.00   0.50    0.05    --  -76.67 111.00  30.00   78
  8  \w    -97.00 -37.00   0.50    0.05    --  -81.00 114.00  60.76  120
  9  \w    -95.00 -45.00   0.50    0.05    --  -81.00 114.00  95.88  100
 10  \w    -60.00 -31.00   0.50    0.05    --  -76.67 111.00 120.00   58
 11  \w    -91.00 -63.00   0.50    0.05    --  -76.67 111.00 120.00   56
 12  \w    -64.00 -32.00   0.50    0.05    --  -76.67 111.00 -30.00   64
 13  \w    -91.00 -66.00   0.50    0.05    --  -76.67 111.00 -30.00   50
 14  \w    -85.00 -31.00   0.50    0.05    --  -76.67 111.00-180.00  108
 15  \w   -126.00 -41.00   0.50    0.05    --  -76.67 -15.00-120.00  170
 16  \w   -121.00 -87.00   0.50    0.05    --  -71.52 -15.00  30.00   68
 17  \w    -69.00 -42.00   0.50    0.05    --  -71.52 -15.00  30.00   54
 18  \w    -74.00 -34.00   0.50    0.05    --  -59.02 -15.00  60.00   80
 19  \w   -125.00 -43.00   0.50    0.05    --  -76.67 -15.00 150.00  164
 20  \w     72.00 109.00   0.50    0.05    --   80.61  15.00-120.00   74
 21  \w     45.00 129.00   0.50    0.05    --   80.61  15.00-180.00  168
 22  \w     36.00  61.00   0.50    0.05    --   80.61-111.00 -30.00   50
 23  \w     23.00  77.00   0.50    0.05    --   55.95-125.00 -30.00  108
 24  \w     37.00  64.00   0.50    0.05    --   80.00-105.00-101.22   54
 25  \w     52.00  88.00   0.50    0.05    --   80.61 -95.00 -90.00   72
 26  \w     65.00  93.00   0.50    0.05    --   80.00-105.00-101.22   56
 27  \w     56.00  88.00   0.50    0.05    --   80.61 -95.00 -60.00   64
 28  \w     42.00  88.00   0.50    0.05    --   80.61 -95.00 -30.00   92
 29  \w     39.00  64.00   0.50    0.05    --   80.61 -95.00  30.00   50
 30  \w     15.00  64.00   0.50    0.05    --   55.95 -95.00 120.00   98
 31  \w     45.00 131.00   0.50    0.05    --   80.61  15.00  90.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0149662000
_diffrn_orient_matrix_UB_12      -0.1161030000
_diffrn_orient_matrix_UB_13      -0.0655141000
_diffrn_orient_matrix_UB_21      0.2255914000
_diffrn_orient_matrix_UB_22      0.0247443000
_diffrn_orient_matrix_UB_23      -0.0436824000
_diffrn_orient_matrix_UB_31      0.0796242000
_diffrn_orient_matrix_UB_32      -0.1088060000
_diffrn_orient_matrix_UB_33      0.0771355000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7663
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.162
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.235
_refine_diff_density_min         -1.741
_refine_diff_density_rms         0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0654
_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^)+(0.1514P)^2^+0.0750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1765
_refine_ls_wR_factor_ref         0.1824
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2674
_reflns_number_total             3029
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00518c1.cif
_cod_data_source_block           240174lt_auto
_cod_depositor_comments
'Adding full bibliography for 7160536--7160537.cif.'
_cod_database_code               7160537
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O Br'
_shelx_estimated_absorpt_t_max   0.795
_shelx_estimated_absorpt_t_min   0.487
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              85767
_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 1.546
_oxdiff_exptl_absorpt_empirical_full_min 0.719