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_7159713
_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         'C16 H10 N2 O6'
_chemical_formula_sum            'C16 H10 N2 O6'
_chemical_formula_weight         326.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-26
_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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2109(2)
_cell_length_b                   7.63020(10)
_cell_length_c                   27.8997(3)
_cell_measurement_reflns_used    40370
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.9710
_cell_measurement_theta_min      4.5740
_cell_volume                     2812.34(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.107a (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 2018/2 (Sheldrick, 2018)'
_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
_diffrn_measured_fraction_theta_full 1.000
_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   -119.00 -34.00   0.50    0.50    --  -47.90 -50.00-133.00  170
  2  \w    -56.00  25.00   0.50    0.50    --  -47.90  50.00  12.00  162
  3  \w    -23.00  56.00   0.50    0.50    --   47.90 -50.00-133.00  158
  4  \w     35.00 120.00   0.50    0.50    --   47.90  50.00  12.00  170
  5  \w    -56.00 -19.00   0.50    2.00    --  -91.75  50.00  12.00   74
  6  \w   -163.00 -78.00   0.50    2.00    --  -91.75 -50.00-133.00  170
  7  \w    100.00 178.00   0.50    2.00    --  113.25  50.00  12.00  156
  8  \w   -119.00 -73.00   0.50    0.50    --  -47.90-125.00  30.00   92
  9  \w   -119.00 -73.00   0.50    0.50    --  -47.90-125.00 -60.00   92
 10  \w   -119.00 -73.00   0.50    0.50    --  -47.90-125.00  60.00   92
 11  \w   -119.00 -33.00   0.50    0.50    --  -47.90 -57.00 120.00  172
 12  \w     36.00 121.00   0.50    0.50    --   47.90  37.00-180.00  170
 13  \w    -26.00  23.00   0.50    0.50    --   47.90 -19.00-120.00   98
 14  \w   -163.00 -76.00   0.50    2.00    --  -91.75 -58.00 136.36  174
 15  \w   -163.00 -72.00   0.50    2.00    --  -91.75 -70.00 120.19  182
 16  \w   -163.00 -69.00   0.50    2.00    --  -91.75 -77.00 150.00  188
 17  \w   -163.00 -69.00   0.50    2.00    --  -91.75 -77.00 120.00  188
 18  \w   -163.00 -77.00   0.50    2.00    --  -91.75 -54.00 155.69  172
 19  \w   -163.00 -76.00   0.50    2.00    --  -91.75 -60.00 117.81  174
 20  \w    -50.00 -20.00   0.50    2.00    --  -91.75  45.00-180.00   60
 21  \w    -50.00 -20.00   0.50    2.00    --  -91.75  45.00 150.00   60
 22  \w   -163.00 -69.00   0.50    2.00    --  -91.75 -77.00  90.00  188
 23  \w    101.00 178.00   0.50    2.00    --  113.25  45.00 -90.00  154
 24  \w     42.00  72.00   0.50    2.00    --  113.25 -61.00  90.00   60
 25  \w     91.00 178.00   0.50    2.00    --  113.25  77.00 129.05  174
 26  \w     42.00 111.00   0.50    2.00    --  113.25-125.00-180.00  138
 27  \w     97.00 178.00   0.50    2.00    --  113.25  61.00 150.00  162
 28  \w     97.00 178.00   0.50    2.00    --  113.25  61.00 120.00  162
 29  \w     42.00  72.00   0.50    2.00    --  113.25 -61.00-150.00   60
 30  \w     42.00 111.00   0.50    2.00    --  113.25-125.00  90.00  138
 31  \w    101.00 178.00   0.50    2.00    --  113.25  45.00-180.00  154
 32  \w     95.00 178.00   0.50    2.00    --  113.25 125.00   0.00  166
 33  \w    101.00 178.00   0.50    2.00    --  113.25  45.00-150.00  154
 34  \w     42.00  72.00   0.50    2.00    --  113.25 -61.00  60.00   60
 35  \w     91.00 178.00   0.50    2.00    --  113.25  77.00  30.00  174
 36  \w     42.00 106.00   0.50    2.00    --  113.25 -94.00 -60.00  128
 37  \w    101.00 178.00   0.50    2.00    --  113.25  45.00 -30.00  154
 38  \w     91.00 178.00   0.50    2.00    --  113.25  77.00  60.00  174
 39  \w     95.00 178.00   0.50    2.00    --  113.25 125.00  90.00  166
 40  \w     95.00 178.00   0.50    2.00    --  113.25 125.00-120.00  166
 41  \w     42.00 106.00   0.50    2.00    --  113.25 -94.00-150.00  128
 42  \w     91.00 178.00   0.50    2.00    --  113.25  77.00 120.00  174
 43  \w     42.00  72.00   0.50    2.00    --  113.25 -61.00-180.00   60
 44  \w     42.00  72.00   0.50    2.00    --  113.25 -61.00 150.00   60
 45  \w    101.00 178.00   0.50    2.00    --  113.25  45.00 -60.00  154
 46  \w     91.00 178.00   0.50    2.00    --  113.25  77.00  90.00  174
 47  \w    101.00 178.00   0.50    2.00    --  113.25  30.00 120.00  154
 48  \w     42.00 111.00   0.50    2.00    --  113.25-125.00  30.00  138
 49  \w    100.00 178.00   0.50    2.00    --  113.25  15.00 120.00  156
 50  \w   -119.00 -25.00   0.50    0.50    --  -47.90 -77.00  30.00  188
 51  \w   -119.00 -25.00   0.50    0.50    --  -47.90 -77.00 120.00  188
 52  \w   -119.00 -25.00   0.50    0.50    --  -47.90 -77.00  60.00  188
 53  \w   -119.00 -25.00   0.50    0.50    --  -47.90 -77.00 -30.00  188
 54  \w   -119.00 -25.00   0.50    0.50    --  -47.90 -77.00-150.00  188
 55  \w   -119.00 -25.00   0.50    0.50    --  -47.90 -77.00 -90.00  188
 56  \w     34.00  96.00   0.50    0.50    --   47.90-125.00  90.00  124
 57  \w     36.00 121.00   0.50    0.50    --   47.90  37.00 -60.00  170
 58  \w     34.00  96.00   0.50    0.50    --   47.90-125.00 150.00  124
 59  \w   -163.00-101.00   0.50    2.00    --  -91.75 -77.00   0.00  124
 60  \w   -163.00 -69.00   0.50    2.00    --  -91.75 -77.00 -71.83  188
 61  \w     42.00  72.00   0.50    2.00    --  113.25 -61.00   0.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0607336000
_diffrn_orient_matrix_UB_12      -0.0013078000
_diffrn_orient_matrix_UB_13      0.0526536000
_diffrn_orient_matrix_UB_21      -0.1085068000
_diffrn_orient_matrix_UB_22      0.0960693000
_diffrn_orient_matrix_UB_23      0.0099007000
_diffrn_orient_matrix_UB_31      -0.1591894000
_diffrn_orient_matrix_UB_32      -0.0659722000
_diffrn_orient_matrix_UB_33      0.0133907000
_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  0.0631
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            79612
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         86.849
_diffrn_reflns_theta_min         3.168
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.028
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.107a (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    1.541
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+3.0954P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2849
_reflns_number_total             3102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01712e2.cif
_cod_data_source_block           sf7
_cod_depositor_comments
'Adding full bibliography for 7159712--7159715.cif.'
_cod_database_code               7159713
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_chemical_oxdiff_usercomment
'C20 H20 N2 O2  colourless block   0.01 0.10 0.20'
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.821
_reflns_odcompleteness_completeness 99.97
_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
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17)
;
_shelx_res_checksum              20079
_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 2.384
_oxdiff_exptl_absorpt_empirical_full_min 0.614