1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide-Alkyne Cycloaddition: A One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles.
Govdi, Anastasia I.; Danilkina, Natalia A.; Ponomarev, Alexander V.; Balova, Irina A.; The Journal of organic chemistry 84 (2019) 1925–1940; doi:10.1021/acs.joc.8b02916

data_4033778
_publ_section_title
;
 1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide-Alkyne Cycloaddition: A
 One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1925
_journal_page_last               1940
_journal_paper_doi               10.1021/acs.joc.8b02916
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H18 F3 N3 O'
_chemical_formula_sum            'C25 H18 F3 N3 O'
_chemical_formula_weight         433.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6472(2)
_cell_length_b                   13.1667(4)
_cell_length_c                   20.5771(7)
_cell_measurement_reflns_used    5558
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.5140
_cell_measurement_theta_min      3.9220
_cell_volume                     2071.88(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -73.00 -36.00   0.50    0.33    --  -41.35 112.00 -26.00   74
  2  \w    -84.00 -35.00   0.50    0.33    --  -41.35 -30.00  89.00   98
  3  \w    -29.00  -3.00   0.50    0.33    --  -41.35  30.00-109.00   52
  4  \w    -10.00  16.00   0.50    0.33    --  -41.35  97.00  75.00   52
  5  \w     66.00  91.00   0.50    0.33    --   41.35  30.00-109.00   50
  6  \w     -7.00  36.00   0.50    0.33    --   41.35-112.00-118.00   86
  7  \w     34.00  59.00   0.50    0.33    --   41.35  30.00-109.00   50
  8  \w     26.00  61.00   0.50    0.33    --   41.35 -97.00 -32.00   70
  9  \w     46.00  73.00   0.50    1.32    --  101.00 -97.00 -32.00   54
 10  \w     84.00 157.00   0.50    1.32    --  101.00  97.00  75.00  146
 11  \w     40.00  99.00   0.50    1.32    --  101.00 -30.00  89.00  118
 12  \w     36.00  74.00   0.50    1.32    --  101.00-112.00-118.00   76
 13  \w    101.00 126.00   0.50    1.32    --  101.00  30.00-109.00   50
 14  \w    -12.00  13.00   0.50    0.33    --   41.35 -30.00  89.00   50
 15  \w     30.00  59.00   0.50    0.33    --   41.35 -54.00   0.00   58
 16  \w     40.00 104.00   0.50    0.33    --   41.35  43.00  60.00  128
 17  \w     -5.00  49.00   0.50    0.33    --   41.35 -43.00 -90.00  108
 18  \w    -12.00  13.00   0.50    0.33    --   41.35 -54.00   0.00   50
 19  \w     36.00 100.00   0.50    1.32    --  101.00 -87.00-180.00  128
 20  \w     35.00  95.00   0.50    1.32    --  101.00-111.00   0.00  120
 21  \w     87.00 124.00   0.50    1.32    --  101.00-133.00 -30.00   74
 22  \w     40.00  84.00   0.50    1.32    --  101.00-133.00 -30.00   88
 23  \w    115.00 140.00   0.50    1.32    --  101.00  33.00-150.00   50
 24  \w     94.00 149.00   0.50    1.32    --  101.00  25.00 150.00  110
 25  \w     54.00  86.00   0.50    1.32    --  101.00 -33.00 -30.00   64
 26  \w     10.00  37.00   0.50    0.33    --   41.35 -89.00  30.00   54
 27  \w     73.00 100.00   0.50    0.33    --   41.35  54.00 -30.00   54
 28  \w     43.00  71.00   0.50    1.32    --  101.00-111.00 -30.00   56
 29  \w     81.00 108.00   0.50    1.32    --  101.00 111.00 150.00   54
 30  \w    125.00 150.00   0.50    1.32    --  101.00 178.00 -30.00   50
 31  \w     83.00 109.00   0.50    1.32    --  101.00 111.00 120.00   52
 32  \w    116.00 157.00   0.50    1.32    --  101.00 111.00 120.00   82
 33  \w     73.00 102.00   0.50    1.32    --  101.00-111.00 -30.00   58
 34  \w     43.00  99.00   0.50    1.32    --  101.00 178.00 -30.00  112
 35  \w     34.00 115.00   0.50    1.32    --  101.00 -17.00 -30.00  162
 36  \w     75.00 119.00   0.50    1.32    --  101.00 -59.00 -60.00   88
 37  \w     42.00  94.00   0.50    1.32    --  101.00-111.00 150.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1767404000
_diffrn_orient_matrix_UB_12      0.0447508000
_diffrn_orient_matrix_UB_13      -0.0219632000
_diffrn_orient_matrix_UB_21      -0.0696875000
_diffrn_orient_matrix_UB_22      -0.0088094000
_diffrn_orient_matrix_UB_23      0.0699615000
_diffrn_orient_matrix_UB_31      0.0677315000
_diffrn_orient_matrix_UB_32      0.1076878000
_diffrn_orient_matrix_UB_33      0.0148373000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10895
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.949
_diffrn_reflns_theta_min         3.986
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.20(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3727
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0605P)^2^+0.1687P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                3536
_reflns_number_total             3727
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02916_si_004.cif
_cod_data_source_block           5699-9975_gai-856
_cod_database_code               4033778
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C25 H18 F3 N3 O'
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.917
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C17(H17), C18(H18), C25(H25), C14(H14), C15(H15), C28(H28), C9(H9),
 C32(H32), C29(H29), C30(H30), C10(H10), C31(H31)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.545
_oxdiff_exptl_absorpt_empirical_full_min 0.481