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_7159715
_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         'C34 H32 N2 O6 S2'
_chemical_formula_sum            'C34 H32 N2 O6 S2'
_chemical_formula_weight         628.73
_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             2021-11-21
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2023-06-26 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.8900(10)
_cell_angle_beta                 108.0600(10)
_cell_angle_gamma                105.6680(10)
_cell_formula_units_Z            4
_cell_length_a                   10.96210(10)
_cell_length_b                   17.2319(2)
_cell_length_c                   17.6310(2)
_cell_measurement_reflns_used    70932
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.4490
_cell_measurement_theta_min      2.5910
_cell_volume                     3030.75(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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     -2.00  31.00   1.00    3.00    --   34.00  87.00 -26.45   33
  2  \w     -4.00  24.00   1.00    3.00    --   34.00  91.00 171.39   28
  3  \w     -4.00  24.00   1.00    3.00    --   34.00  91.00-110.46   28
  4  \w   -116.00 -17.00   1.00    3.00    --  -41.82 -37.00 -30.00   99
  5  \w    -70.00  31.00   1.00    3.00    --  -41.82  57.00 150.00  101
  6  \w   -116.00 -17.00   1.00    3.00    --  -41.82 -37.00  60.00   99
  7  \w   -116.00 -17.00   1.00    3.00    --  -41.82 -37.00 150.00   99
  8  \w    -30.00  70.00   1.00    3.00    --   41.82 -57.00 -30.00  100
  9  \w     27.00  98.00   1.00    3.00    --   41.82-125.00 -90.00   71
 10  \w     16.00  42.00   1.00    3.00    --   50.00  81.00-118.97   26
 11  \w     16.00  42.00   1.00    3.00    --   50.00  81.00  28.82   26
 12  \w     16.00  42.00   1.00    3.00    --   50.00  81.00 -90.07   26
 13  \w     16.00  42.00   1.00    3.00    --   50.00  82.00  -4.84   26
 14  \w     16.00  42.00   1.00    3.00    --   50.00  81.00-176.31   26
 15  \w     16.00  42.00   1.00    3.00    --   50.00  82.00 111.00   26
 16  \w     16.00  42.00   1.00    3.00    --   50.00  81.00 102.04   26
 17  \w     31.00 135.00   1.00    3.00    --   62.00  69.00 -20.22  104
 18  \w     35.00 139.00   1.00    3.00    --   66.00  69.00  19.97  104
 19  \w     35.00 140.00   1.00    3.00    --   66.00  70.00 -60.63  105
 20  \w     35.00 140.00   1.00    3.00    --   66.00  71.00  60.78  105
 21  \w     35.00 140.00   1.00    3.00    --   66.00  71.00  95.42  105
 22  \w     39.00 143.00   1.00    3.00    --   70.00  69.00 135.96  104
 23  \w     39.00 144.00   1.00    3.00    --   70.00  71.00-101.45  105
 24  \w     39.00 144.00   1.00    3.00    --   70.00  70.00 165.08  105
 25  \w     39.00 144.00   1.00    3.00    --   70.00  70.00-155.15  105
 26  \w     40.00 143.00   1.00    3.00    --   70.00  67.00  44.65  103
 27  \w     39.00 143.00   1.00    3.00    --   70.00  69.00-126.91  104
 28  \w     49.00 151.00   1.00   12.00    --   78.00  59.00 -44.16  102
 29  \w     51.00 156.00   1.00   12.00    --   82.00  71.00-141.87  105
 30  \w     55.00 160.00   1.00   12.00    --   86.00  70.00-121.76  105
 31  \w     60.00 163.00   1.00   12.00    --   90.00  67.00 -90.35  103
 32  \w     78.00 178.00   1.00   12.00    --  107.00  61.00 150.00  100
 33  \w     78.00 178.00   1.00   12.00    --  107.00  61.00   0.00  100
 34  \w     78.00 178.00   1.00   12.00    --  107.00  61.00 -90.00  100
 35  \w     34.00 133.00   1.00   12.00    --  107.00 -45.00 -90.00   99
 36  \w     81.00 178.00   1.00   12.00    --  107.00  45.00 120.00   97
 37  \w     24.00 107.00   1.00   12.00    --  107.00 -94.00 -60.00   83
 38  \w     24.00 107.00   1.00   12.00    --  107.00 -94.00  90.00   83
 39  \w     37.00 127.00   1.00   12.00    --  107.00-145.00 -80.50   90
 40  \w     78.00 178.00   1.00   12.00    --  107.00  59.00 174.59  100
 41  \w     81.00 178.00   1.00   12.00    --  107.00  45.00   0.00   97
 42  \w     78.00 178.00   1.00   12.00    --  107.00  61.00 120.00  100
 43  \w     78.00 178.00   1.00   12.00    --  107.00  61.00-180.00  100
 44  \w     79.00 178.00   1.00   12.00    --  107.00  58.00  10.33   99
 45  \w     34.00 133.00   1.00   12.00    --  107.00 -45.00  90.00   99
 46  \w     97.00 178.00   1.00   12.00    --  107.00 125.00-150.00   81
 47  \w     34.00 112.00   1.00   12.00    --  107.00-125.00 -30.00   78
 48  \w     78.00 178.00   1.00   12.00    --  107.00  61.00-150.00  100
 49  \w     82.00 178.00   1.00   12.00    --  107.00  42.00 103.00   96
 50  \w     35.00 136.00   1.00   12.00    --  107.00 -61.00  30.00  101
 51  \w     78.00 178.00   1.00   12.00    --  107.00  61.00 -60.00  100
 52  \w     78.00 178.00   1.00   12.00    --  107.00  61.00  90.00  100
 53  \w     97.00 178.00   1.00   12.00    --  107.00 125.00 -90.00   81
 54  \w     78.00 178.00   1.00   12.00    --  107.00  61.00  30.00  100
 55  \w     35.00 136.00   1.00   12.00    --  107.00 -61.00 -90.00  101
 56  \w     79.00 178.00   1.00   12.00    --  107.00  54.00 -30.79   99
 57  \w     34.00 112.00   1.00   12.00    --  107.00-125.00 -60.00   78
 58  \w     97.00 178.00   1.00   12.00    --  107.00 125.00   0.00   81
 59  \w     97.00 178.00   1.00   12.00    --  107.00 125.00-120.00   81
 60  \w     34.00 112.00   1.00   12.00    --  107.00-125.00 120.00   78
 61  \w     34.00 112.00   1.00   12.00    --  107.00-125.00  90.00   78
 62  \w     24.00 107.00   1.00   12.00    --  107.00 -94.00   0.00   83
 63  \w     81.00 178.00   1.00   12.00    --  107.00  45.00 -60.00   97
 64  \w     34.00 112.00   1.00   12.00    --  107.00-125.00-150.00   78
 65  \w     78.00 178.00   1.00   12.00    --  107.00  61.00 -30.00  100
 66  \w     78.00 178.00   1.00   12.00    --  107.00  61.00-120.00  100
 67  \w     81.00 178.00   1.00   12.00    --  107.00  45.00 150.00   97
 68  \w     78.00 178.00   1.00   12.00    --  107.00  61.00  60.00  100
 69  \w      2.00  30.00   1.00    3.00    --   38.00  88.00  85.47   28
 70  \w    -74.00  34.00   1.00    3.00    --  -41.82  77.00 -30.00  108
 71  \w    -74.00  34.00   1.00    3.00    --  -41.82  77.00-180.00  108
 72  \w    -74.00  34.00   1.00    3.00    --  -41.82  77.00-150.00  108
 73  \w    -74.00  34.00   1.00    3.00    --  -41.82  77.00 -60.00  108
 74  \w   -114.00 -14.00   1.00    3.00    --  -41.82 -57.00-150.00  100
 75  \w    -74.00  34.00   1.00    3.00    --  -41.82  77.00 -90.00  108
 76  \w    -74.00  34.00   1.00    3.00    --  -41.82  77.00   0.00  108
 77  \w    -74.00  34.00   1.00    3.00    --  -41.82  77.00-120.00  108
 78  \w     27.00  98.00   1.00    3.00    --   41.82-125.00-180.00   71
 79  \w     16.00  42.00   1.00    3.00    --   50.00  81.00 -29.32   26
 80  \w     27.00 132.00   1.00    3.00    --   58.00  71.00-171.89  105
 81  \w     27.00 132.00   1.00    3.00    --   58.00  70.00  -1.69  105
 82  \w     27.00 132.00   1.00    3.00    --   58.00  71.00 -30.60  105
 83  \w     31.00 136.00   1.00    3.00    --   62.00  71.00  48.58  105
 84  \w     31.00 136.00   1.00    3.00    --   62.00  71.00 140.94  105
 85  \w     31.00 136.00   1.00    3.00    --   62.00  71.00 -64.25  105
 86  \w     31.00 135.00   1.00    3.00    --   62.00  69.00 -96.77  104
 87  \w     44.00 143.00   1.00    3.00    --   70.00  46.00 104.17   99
 88  \w     39.00 144.00   1.00    3.00    --   70.00  70.00 -60.21  105
 89  \w     45.00 143.00   1.00    3.00    --   70.00  43.00  10.80   98
 90  \w     42.00 143.00   1.00    3.00    --   70.00  58.00 112.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1025351000
_diffrn_orient_matrix_UB_12      0.0011093000
_diffrn_orient_matrix_UB_13      -0.0434353000
_diffrn_orient_matrix_UB_21      -0.0027642000
_diffrn_orient_matrix_UB_22      0.0856526000
_diffrn_orient_matrix_UB_23      -0.0225644000
_diffrn_orient_matrix_UB_31      0.1153947000
_diffrn_orient_matrix_UB_32      0.0371962000
_diffrn_orient_matrix_UB_33      0.0784084000
_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  0.0632
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            146215
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.646
_diffrn_reflns_theta_min         2.652
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.004
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
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    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     797
_refine_ls_number_reflns         12178
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0465P)^2^+1.4858P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11192
_reflns_number_total             12178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01712e2.cif
_cod_data_source_block           mw14
_cod_depositor_comments
'Adding full bibliography for 7159712--7159715.cif.'
_cod_original_cell_volume        3030.74(6)
_cod_database_code               7159715
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 N2 O2 S'
_chemical_oxdiff_usercomment
'C20 H20 N2 O2 S colourless block   0.14 0.2 0.2'
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.795
_reflns_odcompleteness_completeness 98.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.08
_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:
 C111(H11A,H11B), C110(H11C,H11D), C210(H21A,H21B), C212(H21C,H21D), C109(H10A,
 H10B), C112(H11E,H11F), C211(H21E,H21F), C127(H12A,H12B), C209(H20A,H20B),
 C230(H23A,H23B), C130(H13A,H13B), C227(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C123(H123), C124(H124), C122(H122), C101(H101), C105(H105), C238(H238),
 C217(H217), C115(H115), C215(H215), C138(H138), C216(H216), C104(H104),
 C102(H102), C116(H116), C117(H117), C134(H134), C137(H137), C234(H234),
 C237(H237), C235(H235), C224(H224), C222(H222), C135(H135), C223(H223),
 C205(H205), C201(H201), C204(H204), C202(H202)
2.c Idealised Me refined as rotating group:
 C3A(H3AA,H3AB,H3AC), C36A(H36A,H36B,H36C), C36B(H36D,H36E,H36F), C3B(H3BA,
 H3BB,H3BC)
;
_shelx_res_checksum              81886
_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 1.511
_oxdiff_exptl_absorpt_empirical_full_min 0.815