Increasing the versatility of the biphenyl-fused-dioxacyclodecyne class of strained alkynes.
Forshaw, Sam; Parker, Jeremy S.; Scott, William T.; Knighton, Richard C.; Tiwari, Neelam; Oladeji, Samson M.; Stevens, Andrew C.; Chew, Yean Ming; Reber, Jami; Clarkson, Guy J.; Balasubramanian, Mohan K.; Wills, Martin; Organic & biomolecular chemistry 22 (2024) 590–605; doi:10.1039/d3ob01712e

data_7159714
_publ_section_title
;
 Increasing the versatility of the biphenyl-fused-dioxacyclodecyne class
 of strained alkynes.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              590
_journal_page_last               605
_journal_paper_doi               10.1039/d3ob01712e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C22 H24 N2 O6 S2'
_chemical_formula_sum            'C22 H24 N2 O6 S2'
_chemical_formula_weight         476.55
_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     direct
_audit_creation_date             2023-03-26
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-06-26 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.075(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6603(3)
_cell_length_b                   11.3987(2)
_cell_length_c                   14.7403(3)
_cell_measurement_reflns_used    26741
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.0880
_cell_measurement_theta_min      4.9600
_cell_volume                     2205.46(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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   -122.00 -27.00   0.50    1.25    --  -48.98 -66.00 -60.00  190
  2  \w    -71.00  24.00   0.50    1.25    --  -48.98  66.00  74.00  190
  3  \w    -24.00  71.00   0.50    1.25    --   49.23 -66.00 -60.00  190
  4  \w     28.00 122.00   0.50    1.25    --   49.23  66.00  74.00  188
  5  \w   -155.00 -61.00   0.50    5.00    --  -82.46 -66.00 -60.00  188
  6  \w    -79.00  -9.00   0.50    5.00    --  -82.46  66.00  74.00  140
  7  \w     36.00  79.00   0.50    5.00    --  108.40 -66.00 -60.00   86
  8  \w     87.00 178.00   0.50    5.00    --  108.40  66.00  74.00  182
  9  \w   -121.00 -79.00   0.50    1.25    --  -48.98-125.00   0.00   84
 10  \w     23.00 118.00   0.50    1.25    --   49.23  77.00-150.00  190
 11  \w    -29.00  26.00   0.50    1.25    --   49.23 -19.00 -60.00  110
 12  \w    -71.00  -8.00   0.50    5.00    --  -82.46  61.00 120.00  126
 13  \w    -35.00  -3.00   0.50    5.00    --  -82.46  30.00 -90.00   64
 14  \w    -51.00  -4.00   0.50    5.00    --  -82.46  45.00-150.00   94
 15  \w   -157.00 -62.00   0.50    5.00    --  -82.46 -61.00   0.00  190
 16  \w   -151.00 -83.00   0.50    5.00    --  -82.46 -94.00-180.00  136
 17  \w    -35.00  -3.00   0.50    5.00    --  -82.46  30.00  90.00   64
 18  \w   -160.00 -66.00   0.50    5.00    --  -82.46 -45.00-150.00  188
 19  \w    -35.00  -3.00   0.50    5.00    --  -82.46  30.00-120.00   64
 20  \w    -71.00  -8.00   0.50    5.00    --  -82.46  61.00  30.00  126
 21  \w   -157.00 -62.00   0.50    5.00    --  -82.46 -61.00-180.00  190
 22  \w     92.00 178.00   0.50    5.00    --  108.40  45.00 120.00  172
 23  \w     34.00  71.00   0.50    5.00    --  108.40 -61.00 -90.00   74
 24  \w     40.00 105.00   0.50    5.00    --  108.40 -94.00  30.00  130
 25  \w     82.00 177.00   0.50    5.00    --  108.40  77.00 150.00  190
 26  \w     88.00 178.00   0.50    5.00    --  108.40  30.00 150.00  180
 27  \w     82.00 177.00   0.50    5.00    --  108.40  77.00-180.00  190
 28  \w     92.00 178.00   0.50    5.00    --  108.40  45.00 -30.00  172
 29  \w     34.00  71.00   0.50    5.00    --  108.40 -61.00 150.00   74
 30  \w     40.00 102.50   0.50    5.00    --  108.40 -94.00-120.00  125
 31  \w     88.00 178.00   0.50    5.00    --  108.40  30.00 -90.00  180
 32  \w     95.00 178.00   0.50    5.00    --  108.40 125.00   0.00  166
 33  \w     88.00 178.00   0.50    5.00    --  108.40  61.00-150.00  180
 34  \w     92.00 178.00   0.50    5.00    --  108.40  45.00   0.00  172
 35  \w     88.00 178.00   0.50    5.00    --  108.40  30.00  60.00  180
 36  \w     40.00 106.00   0.50    5.00    --  108.40 -77.00  30.00  132
 37  \w     34.00  71.00   0.50    5.00    --  108.40 -61.00 -60.00   74
 38  \w     82.00 177.00   0.50    5.00    --  108.40  77.00  90.00  190
 39  \w     88.00 178.00   0.50    5.00    --  108.40  30.00-180.00  180
 40  \w     34.00  71.00   0.50    5.00    --  108.40 -61.00-180.00   74
 41  \w     36.00  97.50   0.50    5.00    --  108.40-125.00  30.00  123
 42  \w     34.00  71.00   0.50    5.00    --  108.40 -61.00-120.00   74
 43  \w   -117.00 -40.00   0.50    1.25    --  -48.98 -77.00-150.00  154
 44  \w   -117.00 -22.00   0.50    1.25    --  -48.98 -77.00  90.00  190
 45  \w   -117.00 -62.50   0.50    1.25    --  -48.98 -77.00 -90.00  109
 46  \w   -117.00 -22.00   0.50    1.25    --  -48.98 -77.00 -30.00  190
 47  \w   -117.00 -22.00   0.50    1.25    --  -48.98 -77.00  30.00  190
 48  \w   -117.00 -22.00   0.50    1.25    --  -48.98 -77.00 150.00  190
 49  \w     34.00 104.00   0.50    1.25    --   49.23-125.00-150.00  140
 50  \w   -151.00 -56.00   0.50    5.00    --  -82.46 -77.00 -30.00  190
 51  \w   -151.00 -87.00   0.50    5.00    --  -82.46 -77.00 -90.00  128
 52  \w   -151.00 -56.00   0.50    5.00    --  -82.46 -77.00  60.00  190
 53  \w   -151.00 -56.00   0.50    5.00    --  -82.46 -77.00 120.00  190
 54  \w   -151.00 -56.00   0.50    5.00    --  -82.46 -77.00 150.00  190
 55  \w     34.00  71.00   0.50    5.00    --  108.40 -61.00  60.00   74
 56  \w     82.00 177.00   0.50    5.00    --  108.40  77.00 -90.00  190
 57  \w     36.00 112.00   0.50    5.00    --  108.40-125.00 150.00  152
 58  \w     40.00  83.00   0.50    5.00    --  108.40 -94.00 -90.00   86
 59  \w     40.00 105.00   0.50    5.00    --  108.40 -94.00 150.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0748639000
_diffrn_orient_matrix_UB_12      0.1015972000
_diffrn_orient_matrix_UB_13      -0.0367212000
_diffrn_orient_matrix_UB_21      0.0416196000
_diffrn_orient_matrix_UB_22      0.0126130000
_diffrn_orient_matrix_UB_23      -0.0865754000
_diffrn_orient_matrix_UB_31      -0.0802265000
_diffrn_orient_matrix_UB_32      -0.0882965000
_diffrn_orient_matrix_UB_33      -0.0546392000
_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  0.0896
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            64880
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.438
_diffrn_reflns_theta_min         4.980
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.85a (Rigaku Oxford Diffraction, 2023)
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    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0421P)^2^+1.6272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4142
_reflns_number_total             4739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01712e2.cif
_cod_data_source_block           mw50
_cod_depositor_comments
'Adding full bibliography for 7159712--7159715.cif.'
_cod_original_cell_volume        2205.45(7)
_cod_database_code               7159714
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 N2 O2 S'
_chemical_oxdiff_usercomment
'C20 H20 N2 O2 S   colourless block 0.02 0.06 0.12    Wills'
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.749
_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), C18(H18A,H18B), C19(H19A,H19B), C16(H16A,H16B), C2(H2A,H2B),
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C24(H24), C12(H12), C13(H13), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              17502
_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 1.631
_oxdiff_exptl_absorpt_empirical_full_min 0.712