Azido-alkynylation of alkenes through radical-polar crossover.
Borrel, Julien; Waser, Jerome; Chemical science 14 (2023) 9452–9460; doi:10.1039/d3sc03309k

data_1569665
_publ_section_title
;
 Azido-alkynylation of alkenes through radical-polar crossover.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              9452
_journal_page_last               9460
_journal_paper_doi               10.1039/d3sc03309k
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C18 H16 N4 O'
_chemical_formula_sum            'C18 H16 N4 O'
_chemical_formula_weight         304.35
_chemical_name_systematic
N-(4-(1-Azido-4-phenylbut-3-yn-2-yl)phenyl)acetamide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-10-31
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-05-19 deposited with the CCDC.	2023-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   43.729(2)
_cell_length_b                   9.4992(4)
_cell_length_c                   7.5184(3)
_cell_measurement_reflns_used    3508
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      70.4070
_cell_measurement_theta_min      4.0300
_cell_volume                     3123.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_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   -104.00 -73.00   0.50    2.32    --  -67.15   0.00  90.00   62
  2  \w   -102.00 -76.00   0.50    2.32    --  -69.26   0.00 150.00   52
  3  \w    -98.00 -73.00   0.50    2.32    --  -69.26   0.00  30.00   50
  4  \w   -102.00 -72.00   0.50    2.32    --  -67.15   0.00 -60.00   60
  5  \w   -103.00 -73.00   0.50    2.32    --  -67.15   0.00-120.00   60
  6  \w     40.00  75.00   0.50    2.32    --   78.01 -95.00 -90.00   70
  7  \w     34.00  78.00   0.50    2.32    --   69.47 -95.00-150.00   88
  8  \w     28.00  53.00   0.50    2.32    --   66.10 -95.00-180.00   50
  9  \w     28.00  53.00   0.50    2.32    --   66.10 -95.00  30.00   50
 10  \w     34.00  60.00   0.50    2.32    --   69.47-125.00 150.00   52
 11  \w     68.00  94.00   0.50    2.32    --   69.47-125.00 150.00   52
 12  \w     57.00  85.00   0.50    2.32    --   78.01 -95.00 150.00   56
 13  \w     49.00 107.00   0.50    2.32    --   78.01  15.00 120.00  116
 14  \w     84.00 110.00   0.50    2.32    --   78.01  15.00  30.00   52
 15  \w     49.00  74.00   0.50    2.32    --   78.01  15.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0055194000
_diffrn_orient_matrix_UB_12      0.1407976000
_diffrn_orient_matrix_UB_13      0.0964596000
_diffrn_orient_matrix_UB_21      0.0319615000
_diffrn_orient_matrix_UB_22      -0.0100438000
_diffrn_orient_matrix_UB_23      0.0851931000
_diffrn_orient_matrix_UB_31      0.0137741000
_diffrn_orient_matrix_UB_32      0.0799470000
_diffrn_orient_matrix_UB_33      -0.1593125000
_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  0.0431
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11322
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.799
_diffrn_reflns_theta_min         4.044
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     122
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0691P)^2^+1.1968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1460
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2117
_reflns_number_total             3060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03309k2.cif
_cod_data_source_block           jb03-227
_cod_depositor_comments
'Adding full bibliography for 1569664--1569665.cif.'
_cod_original_cell_volume        3123.1(3)
_cod_database_code               1569665
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H16 N4 O1'
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.855
_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. Restrained distances
 C3-C1 \\sim C2-C1
 with sigma of 0.01
 N5-N4 \\sim N6-N5 \\sim N2-N1 \\sim N3-N2
 with sigma of 0.02
 N1-C2 \\sim N4-C3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N1 \\sim N2 \\sim N3 \\sim N4 \\sim N5 \\sim N6 \\sim C1 \\sim C2 \\sim C3:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(N4)=Sof(N5)=Sof(N6)=Sof(H1B)=Sof(C3)=Sof(H3A)=Sof(H3B)=1-FVAR(1)
 Sof(N1)=Sof(N2)=Sof(N3)=Sof(H1A)=Sof(C2)=Sof(H2A)=Sof(H2B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1A), C1(H1B)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
5.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              8311
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.988
_oxdiff_exptl_absorpt_empirical_full_min 0.536