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_7159601
_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      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             2022-11-04
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-08-04 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.1900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.11690(10)
_cell_length_b                   12.31300(10)
_cell_length_c                   14.85260(10)
_cell_measurement_reflns_used    22601
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.7570
_cell_measurement_theta_min      4.6570
_cell_volume                     1662.84(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_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      149.99(10)
_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 0.994
_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    -19.00  27.00   0.50    0.05    --  -47.05  37.00-150.00   92
  2  \w    -59.00  26.00   0.50    0.05    --  -47.05  65.00 -40.00  170
  3  \w      1.00  28.00   0.50    0.05    --  -47.05  19.00 -30.00   54
  4  \w      1.00  28.00   0.50    0.05    --  -47.05  19.00  90.00   54
  5  \w      1.00  28.00   0.50    0.05    --  -47.05  19.00 120.00   54
  6  \w    -19.00  27.00   0.50    0.05    --  -47.05  37.00 150.00   92
  7  \w     28.00 119.00   0.50    0.05    --   47.05  65.00 -40.00  182
  8  \w     82.00 119.00   0.50    0.05    --   47.05  57.00  30.00   74
  9  \w    113.00 154.00   0.50    0.19    --  110.00  77.00  90.00   82
 10  \w    101.00 168.00   0.50    0.19    --  110.00  77.00  30.00  134
 11  \w    101.00 178.00   0.50    0.19    --  110.00  77.00   0.00  154
 12  \w     93.00 178.00   0.50    0.19    --  110.00  61.00  90.00  170
 13  \w     93.00 129.00   0.50    0.19    --  110.00  61.00  30.00   72
 14  \w    137.00 164.00   0.50    0.19    --  110.00  61.00  30.00   54
 15  \w     93.00 178.00   0.50    0.19    --  110.00  61.00   0.00  170
 16  \w     98.00 123.00   0.50    0.19    --  110.00  61.00  60.00   50
 17  \w     91.00 178.00   0.50    0.19    --  110.00  65.00 -40.00  174
 18  \w     96.00 178.00   0.50    0.19    --  110.00  45.00-120.00  164
 19  \w    120.00 166.00   0.50    0.19    --  110.00  77.00-150.00   92
 20  \w     98.00 147.00   0.50    0.19    --  110.00  30.00-150.00   98
 21  \w     82.00 119.00   0.50    0.05    --   47.05  57.00-120.00   74
 22  \w     96.00 178.00   0.50    0.19    --  110.00  30.00-180.00  164
 23  \w     92.00 178.00   0.50    0.19    --  110.00  15.00 -60.00  172
 24  \w     96.00 178.00   0.50    0.19    --  110.00  45.00  60.00  164
 25  \w     96.00 155.00   0.50    0.19    --  110.00  45.00  90.00  118
 26  \w    104.00 130.00   0.50    0.19    --  110.00  45.00 120.00   52
 27  \w     39.00  70.00   0.50    0.19    --  110.00 -45.00 -30.00   62
 28  \w     38.00 134.00   0.50    0.19    --  110.00 -77.00  60.00  192
 29  \w     99.00 133.00   0.50    0.19    --  110.00 -77.00 -60.00   68
 30  \w     53.00  89.00   0.50    0.19    --  110.00 -61.00 -30.00   72
 31  \w     38.00  95.00   0.50    0.19    --  110.00 -77.00 -60.00  114
 32  \w    -25.00  66.00   0.50    0.05    --   47.05 -65.00-176.00  182
 33  \w     38.00 101.00   0.50    0.19    --  110.00 -65.00-176.00  126
 34  \w     38.00  71.00   0.50    0.19    --  110.00 -45.00-180.00   66
 35  \w     39.00  71.00   0.50    0.19    --  110.00 -45.00-120.00   64
 36  \w     38.00  71.00   0.50    0.19    --  110.00 -45.00 -90.00   66
 37  \w     38.00  71.00   0.50    0.19    --  110.00 -45.00 -60.00   66
 38  \w     38.00  63.00   0.50    0.19    --  110.00 -45.00   0.00   50
 39  \w     38.00  71.00   0.50    0.19    --  110.00 -45.00 120.00   66
 40  \w     34.00  94.00   0.50    0.05    --   47.05-125.00   0.00  120
 41  \w     38.00 106.00   0.50    0.19    --  110.00 -94.00 120.00  136
 42  \w     40.00 112.00   0.50    0.19    --  110.00-125.00 -30.00  144
 43  \w     64.00  90.00   0.50    0.19    --  110.00 -94.00 -30.00   52
 44  \w     39.00  89.00   0.50    0.19    --  110.00 -94.00 -90.00  100
 45  \w     38.00 106.00   0.50    0.19    --  110.00 -94.00-120.00  136
 46  \w     38.00 106.00   0.50    0.19    --  110.00 -94.00-150.00  136
 47  \w    -59.00 -15.00   0.50    0.19    --  -88.50  65.00 -40.00   88
 48  \w   -121.00 -32.00   0.50    0.05    --  -47.05 -37.00  60.00  178
 49  \w   -161.00 -74.00   0.50    0.19    --  -88.50 -45.00  60.00  174
 50  \w   -119.00 -82.00   0.50    0.05    --  -47.05 -57.00   0.00   74
 51  \w   -119.00 -28.00   0.50    0.05    --  -47.05 -65.00-176.00  182
 52  \w   -160.00 -69.00   0.50    0.19    --  -88.50 -65.00-176.00  182
 53  \w   -161.00 -15.00   0.50    0.19    --  -88.50   0.00   0.00  292
;
_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      -0.1469095000
_diffrn_orient_matrix_UB_12      -0.0295817000
_diffrn_orient_matrix_UB_13      -0.0520859000
_diffrn_orient_matrix_UB_21      0.0783803000
_diffrn_orient_matrix_UB_22      -0.0887820000
_diffrn_orient_matrix_UB_23      -0.0516172000
_diffrn_orient_matrix_UB_31      -0.0313752000
_diffrn_orient_matrix_UB_32      -0.0830343000
_diffrn_orient_matrix_UB_33      0.0737537000
_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  0.0397
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.047
_diffrn_reflns_theta_min         4.670
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
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    1.360
_exptl_crystal_description       irregular
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0025(3)
_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   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0406P)^2^+0.5535P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0891
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3373
_reflns_number_total             3550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01559a2.cif
_cod_data_source_block           ed-188-lc_auto
_cod_depositor_comments
'Adding full bibliography for 7159600--7159602.cif.'
_cod_database_code               7159601
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C21H16N4O
_chemical_oxdiff_usercomment     150K
_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:
 C1(H1A,H1B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              24129
_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 2.445
_oxdiff_exptl_absorpt_empirical_full_min 0.676