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_7159712
_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         'C23 H19 N O3 S'
_chemical_formula_sum            'C23 H19 N O3 S'
_chemical_formula_weight         389.45
_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     dual
_audit_creation_date             2018-11-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-06-26 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.2723(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.14881(14)
_cell_length_b                   8.79337(7)
_cell_length_c                   15.81288(19)
_cell_measurement_reflns_used    10818
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.8130
_cell_measurement_theta_min      5.8470
_cell_volume                     1949.27(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.919
_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   -118.00  -9.00   1.00   25.00    --  -41.71 -77.00  30.00  109
  2  \w    -50.00  33.00   1.00   25.00    --  -41.71  38.00 -60.00   83
  3  \w    -50.00  33.00   1.00   25.00    --  -41.71  38.00   0.00   83
  4  \w     -4.00  83.00   1.00   25.00    --   41.71 -99.00  30.00   87
  5  \w     18.00  98.00   1.00   25.00    --   41.71-125.00-120.00   80
  6  \w     18.00  98.00   1.00   25.00    --   41.71-125.00 -90.00   80
  7  \w     17.00 116.00   1.00   25.00    --   41.71  38.00 120.00   99
  8  \w     81.00 178.00   1.00  100.00    --  114.00  77.00  60.00   97
  9  \w     85.00 178.00   1.00  100.00    --  114.00  61.00  60.00   93
 10  \w     81.00 178.00   1.00  100.00    --  114.00  77.00  90.00   97
 11  \w    100.00 178.00   1.00  100.00    --  114.00 111.00-180.00   78
 12  \w     88.00 178.00   1.00  100.00    --  114.00  45.00  60.00   90
 13  \w     86.00 178.00   1.00  100.00    --  114.00  30.00 150.00   92
 14  \w     85.00 178.00   1.00  100.00    --  114.00  61.00  30.00   93
 15  \w     38.00  91.00   1.00  100.00    --  114.00 -30.00  90.00   53
 16  \w     41.00  98.00   1.00  100.00    --  114.00 -45.00 150.00   57
 17  \w     85.00 178.00   1.00  100.00    --  114.00  61.00 120.00   93
 18  \w     85.00 178.00   1.00  100.00    --  114.00  61.00  90.00   93
 19  \w     41.00  98.00   1.00  100.00    --  114.00 -45.00  30.00   57
 20  \w     38.00 147.00   1.00  100.00    --  114.00 -77.00-150.00  109
 21  \w     86.00 178.00   1.00  100.00    --  114.00  30.00  90.00   92
 22  \w     88.00 178.00   1.00  100.00    --  114.00  45.00  90.00   90
 23  \w     42.00 113.00   1.00  100.00    --  114.00 -55.00-154.00   71
 24  \w     88.00 178.00   1.00  100.00    --  114.00  45.00-120.00   90
 25  \w     88.00 178.00   1.00  100.00    --  114.00  45.00 120.00   90
 26  \w     86.00 178.00   1.00  100.00    --  114.00  30.00 120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0762154000
_diffrn_orient_matrix_UB_12      0.0134815000
_diffrn_orient_matrix_UB_13      -0.0974436000
_diffrn_orient_matrix_UB_21      0.0557176000
_diffrn_orient_matrix_UB_22      -0.1145778000
_diffrn_orient_matrix_UB_23      -0.0344653000
_diffrn_orient_matrix_UB_31      -0.0562739000
_diffrn_orient_matrix_UB_32      -0.1319007000
_diffrn_orient_matrix_UB_33      0.0198797000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26230
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         89.753
_diffrn_reflns_theta_min         5.662
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0833P)^2^+0.4459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1333
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3656
_reflns_number_total             4102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01712e2.cif
_cod_data_source_block           sf2
_cod_depositor_comments
'Adding full bibliography for 7159712--7159715.cif.'
_cod_database_code               7159712
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 N2 O2 S'
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.825
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C10(H10A,H10B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18), C19(H19),
 C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              79485
_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 1.176
_oxdiff_exptl_absorpt_empirical_full_min 0.876