Three-component acyloxylation of diazo compounds with carboxylic acids and azadienes.
Lin, Meng-Ling; Zheng, Ting; Liu, Hao; Wang, Ying-Xu; Dong, Lin; Organic & biomolecular chemistry 21 (2023) 925–929; doi:10.1039/d2ob02133a

data_7159053
_publ_section_title
;
 Three-component acyloxylation of diazo compounds with carboxylic acids
 and azadienes.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              925
_journal_page_last               929
_journal_paper_doi               10.1039/d2ob02133a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C31 H30 Br N O9 S'
_chemical_formula_sum            'C31 H30 Br N O9 S'
_chemical_formula_weight         672.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2cjspd
_audit_creation_date             2022-07-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-18 deposited with the CCDC.	2022-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.9010(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.09350(10)
_cell_length_b                   13.22240(10)
_cell_length_c                   28.2845(2)
_cell_measurement_reflns_used    28767
_cell_measurement_temperature    298.3(3)
_cell_measurement_theta_max      76.7110
_cell_measurement_theta_min      3.1180
_cell_volume                     3766.11(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.3(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.971
_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    105.00 178.00   0.50    0.39    --  106.01  61.00 -30.00  146
  2  \w    109.00 142.00   0.50    0.39    --  106.01 103.00  22.00   66
  3  \w     93.00 173.00   0.50    0.39    --  106.01  45.00  90.00  160
  4  \w     97.00 153.00   0.50    0.39    --  106.01  30.00 120.00  112
  5  \w    -61.00 -26.00   0.50    0.10    --  -47.30  57.00 -60.00   70
  6  \w    -14.00  25.00   0.50    0.10    --  -47.30  57.00 -60.00   78
  7  \w    -14.00  19.00   0.50    0.10    --  -47.30  19.00 -90.00   66
  8  \w     -8.00  28.00   0.50    0.10    --   47.30 -37.00 -90.00   72
  9  \w    -27.00  27.00   0.50    0.10    --   47.30 -19.00 -60.00  108
 10  \w    -27.00  23.00   0.50    0.10    --   47.30 -19.00   0.00  100
 11  \w     64.00  97.00   0.50    0.39    --  106.01 -94.00  30.00   66
 12  \w     33.00 111.00   0.50    0.39    --  106.01-125.00 120.00  156
 13  \w     34.00  90.00   0.50    0.10    --   47.30-125.00 150.00  112
 14  \w     41.00 117.00   0.50    0.39    --  106.01-125.00  60.00  152
 15  \w     33.00  68.00   0.50    0.39    --  106.01-125.00 -90.00   70
 16  \w     66.00  92.00   0.50    0.39    --  106.01-103.00 -80.00   52
 17  \w     76.00 114.00   0.50    0.39    --  106.01-125.00 -90.00   76
 18  \w     35.00 116.00   0.50    0.39    --  106.01-125.00-150.00  162
 19  \w     34.00 106.00   0.50    0.39    --  106.01-125.00-180.00  144
 20  \w     10.00  55.00   0.50    0.10    --   47.30-103.00 -80.00   90
 21  \w     62.00 108.00   0.50    0.39    --  106.01 -77.00-150.00   92
 22  \w     33.00  71.00   0.50    0.39    --  106.01 -61.00-150.00   76
 23  \w     44.00  69.00   0.50    0.39    --  106.01 -61.00 -90.00   50
 24  \w     33.00  73.00   0.50    0.39    --  106.01 -61.00 -60.00   80
 25  \w     33.00  73.00   0.50    0.39    --  106.01 -61.00 -30.00   80
 26  \w     40.00  65.00   0.50    0.39    --  106.01 -61.00  60.00   50
 27  \w     34.00  59.00   0.50    0.39    --  106.01 -61.00  90.00   50
 28  \w     44.00  70.00   0.50    0.39    --  106.01 -61.00 150.00   52
 29  \w    -63.00 -29.00   0.50    0.39    -- -102.00  77.00 -60.00   68
 30  \w    -66.00 -33.00   0.50    0.39    -- -102.00  61.00 -60.00   66
 31  \w   -100.00 -74.00   0.50    0.39    -- -102.00 103.00  22.00   52
 32  \w   -115.00 -30.00   0.50    0.39    -- -102.00 125.00 -60.00  170
 33  \w    -67.00   9.00   0.50    0.10    --  -47.30 103.00  22.00  152
 34  \w    -69.00 -29.00   0.50    0.39    -- -102.00  61.00  90.00   80
 35  \w   -160.00-100.00   0.50    0.39    -- -102.00 -61.00 -60.00  120
 36  \w   -170.00-120.00   0.50    0.39    -- -102.00 -45.00-180.00  100
 37  \w   -172.00-131.00   0.50    0.39    -- -102.00 -45.00-150.00   82
 38  \w   -127.00 -89.00   0.50    0.39    -- -102.00 -45.00-150.00   76
 39  \w   -173.00 -91.00   0.50    0.39    -- -102.00 -45.00  90.00  164
 40  \w   -119.00 -77.00   0.50    0.10    --  -47.30-125.00  90.00   84
 41  \w   -120.00 -72.00   0.50    0.10    --  -47.30-125.00   0.00   96
 42  \w   -156.00-128.00   0.50    0.39    -- -102.00-103.00 -80.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0476143000
_diffrn_orient_matrix_UB_12      0.0976196000
_diffrn_orient_matrix_UB_13      -0.0232477000
_diffrn_orient_matrix_UB_21      0.1274562000
_diffrn_orient_matrix_UB_22      -0.0544596000
_diffrn_orient_matrix_UB_23      -0.0130046000
_diffrn_orient_matrix_UB_31      -0.0699575000
_diffrn_orient_matrix_UB_32      -0.0328025000
_diffrn_orient_matrix_UB_33      -0.0476592000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            50245
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.886
_diffrn_reflns_theta_min         4.561
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.388
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         7730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0696P)^2^+0.7701P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1258
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6870
_reflns_number_total             7730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02133a2.cif
_cod_data_source_block           exp_2928_auto
_cod_depositor_comments          'Adding full bibliography for 7159053.cif.'
_cod_database_code               7159053
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C1 H1 N1 O1 Br1 S1'
_shelx_estimated_absorpt_t_max   0.716
_shelx_estimated_absorpt_t_min   0.673
_diffrn_oxdiff_digest_frames
;
011c5d593143d3a263ce936adbdbcaad770003821be
;
_diffrn_oxdiff_digest_hkl
;
0165a99e56ff678b4914a3b8c6f8e27bea52f1
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C3(H3)
2.c Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C28(H28A,H28B)
2.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C21(H21), C22(H22), C23(H23), C26(H26), C29(H29)
2.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C)
;
_shelx_res_checksum              99458
_shelx_fab_checksum              92124
_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 1.751
_oxdiff_exptl_absorpt_empirical_full_min 0.827