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

data_7160536
_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         'C22 H22 Br2 O3'
_chemical_formula_sum            'C22 H22 Br2 O3'
_chemical_formula_weight         494.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-18
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-17 deposited with the CCDC.	2025-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.6350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   11.18660(10)
_cell_length_b                   11.41780(10)
_cell_length_c                   63.8254(7)
_cell_measurement_reflns_used    23678
_cell_measurement_temperature    100.01(13)
_cell_measurement_theta_max      74.6560
_cell_measurement_theta_min      2.7580
_cell_volume                     8151.69(14)
_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(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_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    -20.00   6.10   0.30    0.15    --   47.14 -30.00 -60.00   87
  2  \w    -20.00   6.10   0.30    0.15    --   47.14 -30.00 -90.00   87
  3  \w    -21.00   4.20   0.30    0.15    --   47.14 -30.00-120.00   84
  4  \w     29.00  75.20   0.30    0.15    --   90.15-111.00-180.00  154
  5  \w     38.00  78.20   0.30    0.15    --   97.39-111.00 -30.00  134
  6  \w     37.00  91.00   0.30    0.15    --   97.39-111.00  30.00  180
  7  \w     43.00  68.80   0.30    0.15    --   97.39-111.00 150.00   86
  8  \w     60.00  91.50   0.30    0.15    --   90.15 -92.00  90.00  105
  9  \w     55.00  91.00   0.30    0.15    --   93.77-100.00  80.06  120
 10  \w     53.00  92.00   0.30    0.15    --   90.15 -92.00  60.00  130
 11  \w     37.00  65.80   0.30    0.15    --   90.15 -88.00  44.00   96
 12  \w     59.00  87.50   0.30    0.15    --   97.39 -88.00  44.00   95
 13  \w     66.00  91.80   0.30    0.15    --   90.15 -92.00   0.00   86
 14  \w     37.00  62.80   0.30    0.15    --   90.15 -92.00   0.00   86
 15  \w     19.00  44.50   0.30    0.15    --   47.14 -88.00  44.00   85
 16  \w     -6.00  54.00   0.30    0.15    --   52.10 -88.00  44.00  200
 17  \w     39.00  91.20   0.30    0.15    --   97.39 -92.00-180.00  174
 18  \w     43.00  70.00   0.30    0.15    --   97.39 -77.00-180.00   90
 19  \w     30.00  57.00   0.30    0.15    --   90.15 -64.00-120.00   90
 20  \w      2.00  28.10   0.30    0.15    --   52.10 -45.00-120.00   87
 21  \w     30.00  57.00   0.30    0.15    --   90.15 -64.00 -60.00   90
 22  \w     45.00  70.20   0.30    0.15    --   97.39 -77.00 -30.00   84
 23  \w     30.00  55.50   0.30    0.15    --   90.15 -64.00  90.00   85
 24  \w     38.00 105.20   0.30    0.15    --   47.14  45.00 -60.00  224
 25  \w     82.00 119.80   0.30    0.15    --   90.15  50.00-120.00  126
 26  \w    102.00 149.40   0.30    0.15    --   90.15  64.00 -90.00  158
 27  \w    115.00 157.00   0.30    0.15    --   97.39  64.00-120.00  140
 28  \w    111.00 149.10   0.30    0.15    --   90.15  64.00 -60.00  127
 29  \w    137.00 162.20   0.30    0.15    --   97.39  50.00 -90.00   84
 30  \w    105.00 148.20   0.30    0.15    --   97.39  50.00  90.00  144
 31  \w     80.00 155.00   0.30    0.15    --   90.15  50.00 120.00  250
 32  \w     80.00 114.80   0.30    0.15    --   90.15  50.00 150.00  116
 33  \w    111.00 149.10   0.30    0.15    --   90.15  64.00 150.00  127
 34  \w     87.00 115.80   0.30    0.15    --   97.39  50.00 -90.00   96
 35  \w     87.00 161.10   0.30    0.15    --   97.39  50.00-150.00  247
 36  \w    118.00 151.00   0.30    0.15    --   90.15 111.00-150.00  110
 37  \w    115.00 152.20   0.30    0.15    --   90.15 111.00-180.00  124
 38  \w    117.00 143.10   0.30    0.15    --   90.15 111.00   0.00   87
 39  \w    111.00 155.10   0.30    0.15    --   97.39  88.00 160.00  147
 40  \w    -27.00  -0.90   0.30    0.15    --  -50.27  45.00 -90.00   87
 41  \w    -53.00 -21.20   0.30    0.15    --  -81.25  64.00-120.00  106
 42  \w    -71.00 -35.00   0.30    0.15    --  -81.25  77.00 -60.00  120
 43  \w    -27.00  13.20   0.30    0.15    --  -50.27  45.00-150.00  134
 44  \w    -49.00 -22.90   0.30    0.15    --  -81.25  64.00  30.00   87
 45  \w    -53.00 -23.90   0.30    0.15    --  -81.25  64.00  60.00   97
 46  \w    -53.00 -26.00   0.30    0.15    --  -81.25  64.00  90.00   90
 47  \w    -48.00 -21.90   0.30    0.15    --  -81.25  64.00 120.00   87
 48  \w    -57.00 -30.90   0.30    0.15    --  -50.27  88.00 160.00   87
 49  \w    -38.00 -11.90   0.30    0.15    --  -54.97  88.00 160.00   87
 50  \w    -97.00 -70.00   0.30    0.15    --  -85.00 114.00 129.14   90
 51  \w    -58.00 -31.90   0.30    0.15    --  -81.25  88.00 160.00   87
 52  \w   -137.00 -71.00   0.30    0.15    --  -81.25 -38.00 -30.00  220
 53  \w   -139.00 -94.60   0.30    0.15    --  -81.25 -64.00 -90.00  148
 54  \w   -127.00 -94.00   0.30    0.15    --  -81.25 -64.00 -60.00  110
 55  \w   -139.00 -94.00   0.30    0.15    --  -81.25 -64.00  60.00  150
 56  \w   -124.00 -76.90   0.30    0.15    --  -85.00 -52.00  60.33  157
 57  \w   -124.00 -76.00   0.30    0.15    --  -81.25 -50.00  90.00  160
 58  \w   -111.00 -84.00   0.30    0.15    --  -85.00 -57.00 101.21   90
 59  \w   -100.00 -75.70   0.30    0.15    --  -85.00 -50.00  77.83   81
 60  \w   -120.00 -54.00   0.30    0.15    --  -54.97 -45.00-150.00  220
 61  \w   -142.00-115.00   0.30    0.15    --  -81.25-111.00   0.00   90
 62  \w   -141.00-102.00   0.30    0.15    --  -81.25-111.00  60.00  130
 63  \w   -137.00-108.80   0.30    0.15    --  -81.25-111.00  30.00   94
 64  \w   -141.00-111.00   0.30    0.15    --  -81.25-111.00-180.00  100
;
_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      0.0526206000
_diffrn_orient_matrix_UB_12      -0.0263550000
_diffrn_orient_matrix_UB_13      0.0219095000
_diffrn_orient_matrix_UB_21      -0.0461762000
_diffrn_orient_matrix_UB_22      0.1189630000
_diffrn_orient_matrix_UB_23      0.0079308000
_diffrn_orient_matrix_UB_31      -0.1185840000
_diffrn_orient_matrix_UB_32      -0.0579274000
_diffrn_orient_matrix_UB_33      0.0063220000
_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  0.0673
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       79
_diffrn_reflns_limit_l_min       -74
_diffrn_reflns_number            52282
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.758
_diffrn_reflns_theta_min         2.769
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89326
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       plate
_exptl_crystal_F_000             3968
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         3.232
_refine_diff_density_min         -1.861
_refine_diff_density_rms         0.244
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.37(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     982
_refine_ls_number_reflns         13408
_refine_ls_number_restraints     1334
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0926
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1035P)^2^+375.9677P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2425
_refine_ls_wR_factor_ref         0.2435
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_full    0.693
_reflns_Friedel_fraction_max     0.636
_reflns_number_gt                13020
_reflns_number_total             13408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00518c1.cif
_cod_data_source_block           2312120lt3_auto
_cod_depositor_comments
'Adding full bibliography for 7160536--7160537.cif.'
_cod_database_code               7160536
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Br'
_shelx_estimated_absorpt_t_max   0.819
_shelx_estimated_absorpt_t_min   0.509
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.63(6)
 0.37(6)
2. 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
3. Uiso/Uaniso restraints and constraints
Uanis(C87) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(Br16) \\sim Ueq, Uanis(Br54) \\sim Ueq, Uanis(Br53) \\sim Ueq,
Uanis(Br80) \\sim Ueq, Uanis(Br20) \\sim Ueq, Uanis(Br10) \\sim Ueq, Uanis(Br1)
\\sim Ueq, Uanis(Br81) \\sim Ueq, Uanis(O55) \\sim Ueq, Uanis(O17) \\sim Ueq,
Uanis(O106) \\sim Ueq, Uanis(O49) \\sim Ueq, Uanis(O79) \\sim Ueq, Uanis(O82)
\\sim Ueq, Uanis(O103) \\sim Ueq, Uanis(O76) \\sim Ueq, Uanis(O32) \\sim Ueq,
Uanis(O35) \\sim Ueq, Uanis(O109) \\sim Ueq, Uanis(O52) \\sim Ueq, Uanis(C83)
\\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C12) \\sim Ueq,
Uanis(C58) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C93) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C91) \\sim Ueq,
Uanis(C66) \\sim Ueq, Uanis(C110) \\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C88) \\sim Ueq, Uanis(C92) \\sim Ueq,
Uanis(C95) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C3)
\\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C96) \\sim Ueq, Uanis(C65) \\sim Ueq,
Uanis(C28) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C90) \\sim Ueq, Uanis(C99)
\\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C84) \\sim Ueq, Uanis(C86) \\sim Ueq,
Uanis(C43) \\sim Ueq, Uanis(C77) \\sim Ueq, Uanis(C102) \\sim Ueq, Uanis(C31)
\\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C75) \\sim Ueq,
Uanis(C30) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C101)
\\sim Ueq, Uanis(C87) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C24) \\sim Ueq,
Uanis(C47) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C70) \\sim Ueq, Uanis(C72)
\\sim Ueq, Uanis(C78) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C89) \\sim Ueq,
Uanis(C48) \\sim Ueq, Uanis(C98) \\sim Ueq, Uanis(C50) \\sim Ueq, Uanis(C67)
\\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C97) \\sim Ueq, Uanis(C1) \\sim Ueq,
Uanis(C39) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C85)
\\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(C62) \\sim Ueq, Uanis(C94) \\sim Ueq,
Uanis(C8) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C60) \\sim Ueq, Uanis(C37)
\\sim Ueq, Uanis(C105) \\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C100) \\sim Ueq,
Uanis(C74) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C71)
\\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C104) \\sim Ueq, Uanis(C2) \\sim Ueq,
Uanis(C73) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C56) \\sim Ueq, Uanis(C15) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C88) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C100) \\sim Ueq, Uanis(C96) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C50(H50A,H50B), C77(H77A,H77B), C104(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C7(H7), C11(H11), C14(H14), C15(H15), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29),
  C30(H30), C36(H36), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42),
 C43(H43), C44(H44), C45(H45), C46(H46), C47(H47), C58(H58), C59(H59), C62(H62),
  C63(H63), C65(H65), C66(H66), C67(H67), C68(H68), C69(H69), C70(H70),
 C71(H71), C72(H72), C73(H73), C74(H74), C85(H85), C86(H86), C89(H89), C90(H90),
  C92(H92), C93(H93), C94(H94), C95(H95), C96(H96), C97(H97), C98(H98),
 C99(H99), C100(H100), C101(H101)
5.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C34(H34A,H34B,H34C), C51(H51A,H51B,H51C), C56(H56A,H56B,
 H56C), C78(H78A,H78B,H78C), C83(H83A,H83B,H83C), C105(H10C,H10D,H10E),
 C110(H11A,H11B,H11C)
;
_shelx_res_checksum              83508
_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 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.784