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

data_1569664
_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_absolute_configuration rmad
_chemical_formula_moiety         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-02-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-21 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            4
_cell_length_a                   5.80631(11)
_cell_length_b                   7.77611(12)
_cell_length_c                   31.5189(6)
_cell_measurement_reflns_used    7436
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.2260
_cell_measurement_theta_min      2.7760
_cell_volume                     1423.09(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (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 2018/2 (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 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   -101.00 -72.00   0.50    0.40    --  -67.31   0.00 -60.00   58
  2  \w   -103.00 -77.00   0.50    0.40    --  -69.03   0.00 -30.00   52
  3  \w   -101.00 -75.00   0.50    0.40    --  -67.31   0.00   0.00   52
  4  \w   -100.00 -73.00   0.50    0.40    --  -67.31   0.00  60.00   54
  5  \w   -102.00 -74.00   0.50    0.40    --  -69.03   0.00  90.00   56
  6  \w    -70.00 -43.00   0.50    0.40    --  -74.50  83.00 -41.51   54
  7  \w    -83.00 -28.00   0.50    0.40    --  -67.31 125.00  30.00  110
  8  \w    -55.00 -29.00   0.50    0.40    --  -67.31 125.00 -90.00   52
  9  \w    -86.00 -38.00   0.50    0.40    --  -67.31 125.00-150.00   96
 10  \w     95.00 120.00   0.50    0.40    --   77.95  15.00  60.00   50
 11  \w     80.00 106.00   0.50    0.40    --   77.95  15.00 150.00   52
 12  \w     50.00  76.00   0.50    0.40    --   77.95  15.00 150.00   52
 13  \w     50.00  76.00   0.50    0.40    --   77.95  15.00  60.00   52
 14  \w     48.00  99.00   0.50    0.40    --   78.00   7.00  14.78  102
 15  \w     64.00  95.00   0.50    0.40    --   77.95  15.00 -90.00   62
 16  \w     80.00 106.00   0.50    0.40    --   73.72   0.00-150.00   52
 17  \w     40.00  67.00   0.50    0.40    --   73.72   0.00-180.00   54
 18  \w     61.00  87.00   0.50    0.40    --   78.00-138.00   0.12   52
 19  \w     76.00 101.00   0.50    0.40    --   77.95-125.00 -60.00   50
 20  \w     39.00  98.00   0.50    0.40    --   77.95-125.00-150.00  118
 21  \w     41.00  86.00   0.50    0.40    --   77.95-125.00-180.00   90
 22  \w     40.00  66.00   0.50    0.40    --   77.95-125.00 -60.00   52
 23  \w     59.00  85.00   0.50    0.40    --   77.95-125.00 -30.00   52
 24  \w     40.00  75.00   0.50    0.40    --   77.95-125.00   0.00   70
 25  \w     49.00  97.00   0.50    0.40    --   77.95-125.00 -90.00   96
 26  \w     39.00  65.00   0.50    0.40    --   77.95-125.00  30.00   52
 27  \w     73.00  99.00   0.50    0.40    --   77.95-125.00  30.00   52
 28  \w     74.00  99.00   0.50    0.40    --   77.95-125.00  60.00   50
 29  \w     56.00  81.00   0.50    0.40    --   77.95-125.00 150.00   50
 30  \w     87.00 113.00   0.50    0.40    --   78.00 116.00-139.30   52
;
_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      -0.2406418000
_diffrn_orient_matrix_UB_12      -0.0812452000
_diffrn_orient_matrix_UB_13      0.0047691000
_diffrn_orient_matrix_UB_21      -0.0673658000
_diffrn_orient_matrix_UB_22      0.0687459000
_diffrn_orient_matrix_UB_23      -0.0441520000
_diffrn_orient_matrix_UB_31      0.0890799000
_diffrn_orient_matrix_UB_32      -0.1669656000
_diffrn_orient_matrix_UB_33      -0.0204976000
_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  0.0183
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            12451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.554
_diffrn_reflns_theta_min         2.804
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_coef       0.0038(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0297
_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^)+(0.0451P)^2^+0.2253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0782
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2786
_reflns_number_total             2932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03309k2.cif
_cod_data_source_block           jb03-295
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1569664--1569665.cif.
;
_cod_database_code               1569664
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C18 H15 N O2'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.888
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H18A)=Sof(H18C)=Sof(H18E)=1-FVAR(1)
 Sof(H18B)=Sof(H18D)=Sof(H18F)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16)
3.b Disordered Me refined as rotating group:
 C18(H18A,H18B,H18C,H18D,H18E,H18F)
;
_shelx_res_checksum              10488
_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 1.506
_oxdiff_exptl_absorpt_empirical_full_min 0.738