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_7159602
_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         'C22 H17 Cl N4'
_chemical_formula_sum            'C22 H17 Cl N4'
_chemical_formula_weight         372.85
_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             2022-08-19
_audit_creation_method
;FinalCif V119 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2023-08-04 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.1277(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.93403(10)
_cell_length_b                   21.4604(2)
_cell_length_c                   7.91748(8)
_cell_measurement_reflns_used    25365
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.5660
_cell_measurement_theta_min      4.1290
_cell_volume                     1793.45(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_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 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 0.995
_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    -50.00 -24.00   0.50    0.72    --  -86.25  61.00-180.00   52
  2  \w    -15.00  23.00   0.50    0.18    --  -48.74  37.00-180.00   76
  3  \w     -4.00  26.00   0.50    0.18    --  -48.74  24.00  27.00   60
  4  \w    -19.00  23.00   0.50    0.18    --  -48.74  37.00 150.00   84
  5  \w     36.00  86.00   0.50    0.18    --   48.74  56.00 120.31  100
  6  \w     38.00  63.00   0.50    0.18    --   48.74  55.00 161.19   50
  7  \w     38.00  67.00   0.50    0.18    --   48.74  55.00 174.34   58
  8  \w     40.00  96.00   0.50    0.18    --   48.74  37.00  90.00  112
  9  \w     39.00 123.00   0.50    0.18    --   48.74  24.00  27.00  168
 10  \w     36.00 108.00   0.50    0.18    --   48.74  55.00-139.39  144
 11  \w     37.00  62.00   0.50    0.18    --   48.74  54.00-160.69   50
 12  \w     67.00 108.00   0.50    0.18    --   48.74  54.00-160.69   82
 13  \w     93.00 177.00   0.50    0.72    --  107.75  61.00-180.00  168
 14  \w     93.00 155.00   0.50    0.72    --  107.75  61.00-150.00  124
 15  \w    141.00 177.00   0.50    0.72    --  107.75  61.00  60.00   72
 16  \w     93.00 136.00   0.50    0.72    --  107.75  61.00  60.00   86
 17  \w     94.00 143.00   0.50    0.72    --  107.75  61.00  90.00   98
 18  \w    150.00 176.00   0.50    0.72    --  107.75  45.00 120.00   52
 19  \w     93.00 159.00   0.50    0.72    --  107.75  61.00 150.00  132
 20  \w    100.00 153.00   0.50    0.72    --  107.75  45.00 150.00  106
 21  \w     93.00 148.00   0.50    0.72    --  107.75  61.00 120.00  110
 22  \w     99.00 141.00   0.50    0.72    --  107.75  45.00 120.00   84
 23  \w    131.00 178.00   0.50    0.72    --  107.75  30.00 120.00   94
 24  \w    134.00 166.00   0.50    0.72    --  107.75   0.00 150.00   64
 25  \w    102.00 132.00   0.50    0.72    --  107.75  45.00  90.00   60
 26  \w    114.00 139.00   0.50    0.72    --  107.75  24.00  27.00   50
 27  \w    128.00 166.00   0.50    0.72    --  107.75   0.00 -30.00   76
 28  \w    129.00 155.00   0.50    0.72    --  107.75   0.00 -60.00   52
 29  \w    140.00 166.00   0.50    0.72    --  107.75  30.00-180.00   52
 30  \w    101.00 146.00   0.50    0.72    --  107.75  45.00-150.00   90
 31  \w    127.00 159.00   0.50    0.72    --  107.75   0.00  90.00   64
 32  \w     73.00 125.00   0.50    0.72    --  107.75 -77.00 150.00  104
 33  \w     40.00  87.00   0.50    0.72    --  107.75 -61.00  90.00   94
 34  \w     36.00  61.00   0.50    0.72    --  107.75 -45.00  90.00   50
 35  \w     45.00  71.00   0.50    0.72    --  107.75 -45.00   0.00   52
 36  \w     36.00  82.00   0.50    0.72    --  107.75 -61.00 -30.00   92
 37  \w     45.00  84.00   0.50    0.72    --  107.75 -61.00-150.00   78
 38  \w     36.00  69.00   0.50    0.72    --  107.75 -45.00 -90.00   66
 39  \w     36.00  70.00   0.50    0.72    --  107.75 -45.00-120.00   68
 40  \w     36.00  71.00   0.50    0.72    --  107.75 -45.00 -30.00   70
 41  \w    -25.00  46.00   0.50    0.18    --   48.74 -24.00-137.00  142
 42  \w     36.00  70.00   0.50    0.72    --  107.75 -45.00  30.00   68
 43  \w     41.00  66.00   0.50    0.72    --  107.75 -45.00  60.00   50
 44  \w     46.00  71.00   0.50    0.72    --  107.75 -45.00 150.00   50
 45  \w     67.00 106.00   0.50    0.72    --  107.75 -94.00  90.00   78
 46  \w     78.00 104.00   0.50    0.72    --  107.75 -94.00   0.00   52
 47  \w     41.00  71.00   0.50    0.72    --  107.75 -94.00   0.00   60
 48  \w     56.00 108.00   0.50    0.72    --  107.75-125.00-150.00  104
 49  \w     75.00 107.00   0.50    0.72    --  107.75-125.00-180.00   64
 50  \w     41.00  67.00   0.50    0.72    --  107.75-125.00-180.00   52
 51  \w   -123.00 -38.00   0.50    0.18    --  -48.74 -24.00-137.00  170
 52  \w    -99.00 -73.00   0.50    0.72    --  -86.25 -55.00  54.50   52
 53  \w   -103.00 -78.00   0.50    0.72    --  -86.25 -56.00  94.13   50
 54  \w    -99.00 -73.00   0.50    0.72    --  -86.25 -55.00 100.40   52
 55  \w   -104.00 -78.00   0.50    0.72    --  -86.25 -56.00 127.14   52
 56  \w   -101.00 -75.00   0.50    0.72    --  -86.25 -53.00 168.62   52
 57  \w    -99.00 -73.00   0.50    0.72    --  -86.25 -55.00 144.74   52
 58  \w    -99.00 -73.00   0.50    0.72    --  -86.25 -53.00 159.72   52
 59  \w    -98.00 -73.00   0.50    0.72    --  -86.25 -53.00 138.73   50
 60  \w    -99.00 -74.00   0.50    0.72    --  -86.25 -52.00 146.94   50
 61  \w   -102.00 -73.00   0.50    0.72    --  -86.25 -55.00 114.31   58
 62  \w   -100.00 -74.00   0.50    0.72    --  -86.25 -52.00 127.34   52
 63  \w    -98.00 -73.00   0.50    0.72    --  -86.25 -54.00  92.96   50
 64  \w   -101.00 -75.00   0.50    0.72    --  -86.25 -50.00  61.50   52
 65  \w   -102.00 -75.00   0.50    0.72    --  -86.25 -52.00  61.25   54
 66  \w   -133.00 -74.00   0.50    0.72    --  -86.25 -52.00  69.51  118
 67  \w   -138.00 -74.00   0.50    0.72    --  -86.25 -54.00  44.40  128
 68  \w   -161.00 -76.00   0.50    0.72    --  -86.25 -24.00-137.00  170
 69  \w   -108.00 -62.00   0.50    0.18    --  -48.74 -37.00-180.00   92
 70  \w   -117.00 -75.00   0.50    0.72    --  -86.25 -48.00  49.76   84
 71  \w   -100.00 -75.00   0.50    0.72    --  -86.25 -46.00 163.62   50
 72  \w    -99.00 -74.00   0.50    0.72    --  -86.25 -50.00  78.58   50
 73  \w   -117.00 -87.00   0.50    0.18    --  -48.74-125.00 -30.00   60
;
_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      -0.1393568000
_diffrn_orient_matrix_UB_12      -0.0127949000
_diffrn_orient_matrix_UB_13      -0.0040479000
_diffrn_orient_matrix_UB_21      0.0274431000
_diffrn_orient_matrix_UB_22      0.0183933000
_diffrn_orient_matrix_UB_23      0.1943154000
_diffrn_orient_matrix_UB_31      -0.0335964000
_diffrn_orient_matrix_UB_32      0.0682259000
_diffrn_orient_matrix_UB_33      -0.0532209000
_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  0.0817
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            35683
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.865
_diffrn_reflns_theta_min         4.120
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.990
_exptl_absorpt_correction_T_max  0.606
_exptl_absorpt_correction_T_min  0.010
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.61a (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    1.381
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method 'by a slow evaporation method'
_exptl_crystal_size_max          0.825
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0911P)^2^+0.3679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1348
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3510
_reflns_number_total             3757
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01559a2.cif
_cod_data_source_block           ed-20-lc_auto
_cod_depositor_comments
'Adding full bibliography for 7159600--7159602.cif.'
_cod_database_code               7159602
_chemical_oxdiff_formula         CHNCl
_chemical_oxdiff_usercomment     150
_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:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C10(H10), C11(H11), C12(H12), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
;
_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 1.940
_oxdiff_exptl_absorpt_empirical_full_min 0.407
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_shelx_estimated_absorpt_t_min   0.291
_shelx_estimated_absorpt_t_max   0.823
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              9721