Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing an endocyclic heteroatom.
Das, Eshani; Feliciano, Mark Aldren M.; Yamanushkin, Pavel; Lin, Xinsong; Gold, Brian; Organic & biomolecular chemistry 21 (2023) 8857–8862; doi:10.1039/d3ob01559a

data_7159600
_publ_section_title
;
 Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing
 an endocyclic heteroatom.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8857
_journal_page_last               8862
_journal_paper_doi               10.1039/d3ob01559a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C21 H16 N4 O'
_chemical_formula_sum            'C21 H16 N4 O'
_chemical_formula_weight         340.38
_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             2023-04-28
_audit_creation_method
;FinalCif V118 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2023-04-28 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                68.423(3)
_cell_angle_beta                 74.665(3)
_cell_angle_gamma                77.346(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8488(2)
_cell_length_b                   9.8954(3)
_cell_length_c                   12.1031(4)
_cell_measurement_reflns_used    23752
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      76.7720
_cell_measurement_theta_min      4.0140
_cell_volume                     835.20(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (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 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_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   -121.00 -35.00   0.50    1.50    --  -47.84 -33.00-144.00  172
  2  \w     35.00 122.00   0.50    1.50    --   47.84  33.00  14.00  174
  3  \w    -26.00  56.00   0.50    1.50    --   47.84 -33.00-144.00  164
  4  \w   -160.00 -72.00   0.50    6.50    --  -86.25 -33.00-144.00  176
  5  \w     94.00 178.00   0.50    6.50    --  107.75  33.00  14.00  168
  6  \w    -17.00   9.00   0.50    1.50    --   14.00  97.00 -87.43   52
  7  \w    -17.00  10.00   0.50    1.50    --   14.00  95.00 101.14   54
  8  \w      0.00  26.00   0.50    1.50    --   22.00  76.00 126.06   52
  9  \w      2.00  33.00   0.50    1.50    --   22.00  70.00   7.86   62
 10  \w     12.00  39.00   0.50    1.50    --   30.00  66.00 -72.80   54
 11  \w     12.00  39.00   0.50    1.50    --   30.00  66.00 -95.26   54
 12  \w    -42.00 -16.00   0.50    1.50    --  -34.00 -64.00-110.47   52
 13  \w    -44.00 -17.00   0.50    1.50    --  -34.00 -63.00  76.33   54
 14  \w     22.00  52.00   0.50    1.50    --   38.00  59.00  96.78   60
 15  \w     23.00  55.00   0.50    1.50    --   38.00  58.00-154.11   64
 16  \w     22.00  50.00   0.50    1.50    --   38.00  60.00  51.50   56
 17  \w    -52.00 -26.00   0.50    1.50    --  -42.00 -59.00  28.83   52
 18  \w    -65.00 -27.00   0.50    1.50    --  -42.00 -56.00 157.90   76
 19  \w     27.00  65.00   0.50    1.50    --   42.00  56.00 -32.79   76
 20  \w      1.00  28.00   0.50    1.50    --  -47.84  19.00-180.00   54
 21  \w      1.00  28.00   0.50    1.50    --  -47.84  19.00-150.00   54
 22  \w    -14.00  26.00   0.50    1.50    --  -47.84  33.00  14.00   80
 23  \w     34.00  94.00   0.50    1.50    --   47.84-125.00   0.00  120
 24  \w     34.00  94.00   0.50    1.50    --   47.84-125.00  90.00  120
 25  \w     34.00 120.00   0.50    1.50    --   47.84  55.00 172.00  172
 26  \w   -121.00 -35.00   0.50    1.50    --  -50.00 -56.00-156.99  172
 27  \w   -125.00 -39.00   0.50    1.50    --  -54.00 -55.00-134.36  172
 28  \w   -125.00 -39.00   0.50    1.50    --  -54.00 -55.00 -55.23  172
 29  \w   -130.00 -43.00   0.50    1.50    --  -58.00 -56.00 163.44  174
 30  \w     43.00 131.00   0.50    1.50    --   58.00  56.00 -22.04  176
 31  \w   -134.00 -48.00   0.50    1.50    --  -62.00 -50.00  73.27  172
 32  \w   -138.00 -52.00   0.50    1.50    --  -66.00 -52.00  12.57  172
 33  \w   -142.00 -55.00   0.50    1.50    --  -70.00 -55.00-114.32  174
 34  \w   -142.00 -56.00   0.50    1.50    --  -70.00 -52.00  31.65  172
 35  \w   -142.00 -56.00   0.50    1.50    --  -70.00 -54.00 149.23  172
 36  \w   -142.00 -56.00   0.50    1.50    --  -70.00 -54.00 -64.69  172
 37  \w   -142.00 -56.00   0.50    1.50    --  -70.00 -52.00  -5.29  172
 38  \w   -145.00 -59.00   0.50    1.50    --  -74.00 -56.00 117.75  172
 39  \w   -145.00 -59.00   0.50    1.50    --  -74.00 -55.00  71.25  172
 40  \w   -145.00 -60.00   0.50    1.50    --  -74.00 -51.00 -19.20  170
 41  \w   -150.00 -63.00   0.50    6.50    --  -78.00 -56.00 -39.43  174
 42  \w   -150.00 -63.00   0.50    6.50    --  -78.00 -56.00 -80.61  174
 43  \w   -150.00 -64.00   0.50    6.50    --  -78.00 -51.00  49.43  172
 44  \w   -150.00 -63.00   0.50    6.50    --  -78.00 -56.00-169.91  174
 45  \w   -150.00 -63.00   0.50    6.50    --  -78.00 -56.00-144.40  174
 46  \w   -153.00 -67.00   0.50    6.50    --  -82.00 -55.00 154.64  172
 47  \w   -159.00 -73.00   0.50    6.50    --  -86.25 -50.00-129.47  172
 48  \w   -159.00 -73.00   0.50    6.50    --  -86.25 -49.00-165.51  172
 49  \w   -159.00 -72.00   0.50    6.50    --  -86.25 -54.00 137.35  174
 50  \w   -159.00 -72.00   0.50    6.50    --  -86.25 -55.00 -90.87  174
 51  \w    -52.00 -13.00   0.50    6.50    --  -86.25  61.00-180.00   78
 52  \w   -159.00 -72.00   0.50    6.50    --  -86.25 -55.00  43.58  174
 53  \w     91.00 178.00   0.50    6.50    --  107.75  61.00-120.00  174
 54  \w     35.00 106.00   0.50    6.50    --  107.75 -94.00  60.00  142
 55  \w     91.00 178.00   0.50    6.50    --  107.75  61.00  60.00  174
 56  \w     35.00 106.00   0.50    6.50    --  107.75 -94.00  30.00  142
 57  \w     38.00 112.00   0.50    6.50    --  107.75-125.00-150.00  148
 58  \w     35.00 106.00   0.50    6.50    --  107.75 -94.00 -60.00  142
 59  \w     95.00 178.00   0.50    6.50    --  107.75  30.00-180.00  166
 60  \w     91.00 178.00   0.50    6.50    --  107.75  61.00 -60.00  174
 61  \w     91.00 178.00   0.50    6.50    --  107.75  61.00-150.00  174
 62  \w     35.00 131.00   0.50    6.50    --  107.75 -77.00 150.00  192
 63  \w     36.00  71.00   0.50    6.50    --  107.75 -45.00  90.00   70
 64  \w     36.00  71.00   0.50    6.50    --  107.75 -45.00 -60.00   70
 65  \w     95.00 178.00   0.50    6.50    --  107.75  45.00 -30.00  166
 66  \w     91.00 178.00   0.50    6.50    --  107.75  61.00 150.00  174
 67  \w     35.00  94.00   0.50    6.50    --  107.75 -61.00-150.00  118
 68  \w    101.00 178.00   0.50    6.50    --  107.75  77.00  30.00  154
 69  \w     35.00 106.00   0.50    6.50    --  107.75 -94.00   0.00  142
 70  \w     36.00  71.00   0.50    6.50    --  107.75 -45.00  30.00   70
 71  \w     95.00 178.00   0.50    6.50    --  107.75  45.00 120.00  166
 72  \w     91.00 178.00   0.50    6.50    --  107.75  61.00  30.00  174
 73  \w     35.00 106.00   0.50    6.50    --  107.75 -94.00  90.00  142
 74  \w     95.00 178.00   0.50    6.50    --  107.75  45.00 -60.00  166
 75  \w     35.00 106.00   0.50    6.50    --  107.75 -94.00-120.00  142
 76  \w     35.00 106.00   0.50    6.50    --  107.75 -94.00-180.00  142
 77  \w     91.00 178.00   0.50    6.50    --  107.75  61.00 120.00  174
 78  \w     91.00 178.00   0.50    6.50    --  107.75  61.00   0.00  174
 79  \w     36.00  71.00   0.50    6.50    --  107.75 -45.00  60.00   70
 80  \w     91.00 178.00   0.50    6.50    --  107.75  61.00  90.00  174
 81  \w     91.00 178.00   0.50    6.50    --  107.75  61.00 -30.00  174
 82  \w     35.00 106.00   0.50    6.50    --  107.75 -94.00-150.00  142
 83  \w     36.00  71.00   0.50    6.50    --  107.75 -45.00 -30.00   70
 84  \w     36.00  71.00   0.50    6.50    --  107.75 -45.00 150.00   70
 85  \w     91.00 178.00   0.50    6.50    --  107.75  61.00 -90.00  174
 86  \w     91.00 178.00   0.50    6.50    --  107.75  61.00-180.00  174
 87  \w     95.00 178.00   0.50    6.50    --  107.75  45.00  60.00  166
 88  \w     36.00  71.00   0.50    6.50    --  107.75 -45.00 -90.00   70
 89  \w     95.00 178.00   0.50    6.50    --  107.75  45.00   0.00  166
 90  \w     95.00 178.00   0.50    6.50    --  107.75  45.00  90.00  166
 91  \w     35.00 106.00   0.50    6.50    --  107.75 -94.00 120.00  142
 92  \w     35.00 106.00   0.50    6.50    --  107.75 -94.00 -30.00  142
 93  \w    101.00 178.00   0.50    6.50    --  107.75  77.00 150.00  154
 94  \w     95.00 178.00   0.50    6.50    --  107.75  45.00-150.00  166
 95  \w     35.00 106.00   0.50    6.50    --  107.75 -94.00 -90.00  142
 96  \w     36.00  71.00   0.50    6.50    --  107.75 -45.00-120.00   70
 97  \w     12.00  40.00   0.50    1.50    --   30.00  65.00-156.49   56
 98  \w   -119.00 -34.00   0.50    1.50    --  -47.84 -52.00 -59.04  170
 99  \w    -24.00 120.00   0.50    1.50    --   47.84   0.00 -60.00  288
100  \w     34.00 120.00   0.50    1.50    --   47.84  55.00 -67.14  172
101  \w    -24.00  -0.50   0.50    1.50    --   47.84   0.00 -30.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0908478000
_diffrn_orient_matrix_UB_12      -0.1057854000
_diffrn_orient_matrix_UB_13      -0.0251646000
_diffrn_orient_matrix_UB_21      0.1376405000
_diffrn_orient_matrix_UB_22      -0.1288100000
_diffrn_orient_matrix_UB_23      0.0537345000
_diffrn_orient_matrix_UB_31      -0.1224878000
_diffrn_orient_matrix_UB_32      -0.0277919000
_diffrn_orient_matrix_UB_33      0.1265601000
_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  0.0525
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            38664
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.412
_diffrn_reflns_theta_min         4.011
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       irregular
_exptl_crystal_F_000             356
_exptl_crystal_recrystallization_method 'by a slow evaporation method'
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0044(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0474P)^2^+0.2900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3229
_reflns_number_total             3490
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01559a2.cif
_cod_data_source_block           ed-178-lc
_cod_depositor_comments
'Adding full bibliography for 7159600--7159602.cif.'
_cod_original_cell_volume        835.21(5)
_cod_database_code               7159600
_chemical_oxdiff_formula         C21H16N4O
_chemical_oxdiff_usercomment     '100 K'
_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:
 C10(H10A,H10B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.755
_oxdiff_exptl_absorpt_empirical_full_min 0.808
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.877
_shelx_estimated_absorpt_t_max   0.988
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              47646