A metal-free transformation of alkynes to carbonyls directed by remote OH group
Chen, Dao-Qian; Guo, Chun-Huan; Zhang, Heng-Rui; Jin, Dong-Po; Li, Xue-Song; Gao, Pin; Wu, Xin-Xing; Liu, Xue-Yuan; Liang, Yong-Min; Green Chem. 18 (2016) 4176–; doi:10.1039/C6GC01141A

data_7225644
_publ_section_title
;
 A metal-free transformation of alkynes to carbonyls directed by remote OH
 group
;
_journal_issue                   15
_journal_name_full               'Green Chem.'
_journal_page_first              4176
_journal_paper_doi               10.1039/C6GC01141A
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C17 H17 Br O2'
_chemical_formula_sum            'C17 H17 Br O2'
_chemical_formula_weight         333.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-03-30 deposited with the CCDC.
2016-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                75.207(6)
_cell_angle_beta                 81.884(6)
_cell_angle_gamma                72.871(6)
_cell_formula_units_Z            4
_cell_length_a                   9.5598(6)
_cell_length_b                   9.6393(7)
_cell_length_c                   18.0624(12)
_cell_measurement_reflns_used    3085
_cell_measurement_temperature    290.5(9)
_cell_measurement_theta_max      69.4940
_cell_measurement_theta_min      4.9950
_cell_volume                     1533.97(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.5(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
  1 omega   86.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   60.0000 66

  2 omega   85.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000    0.0000 27

  3 omega  125.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 46

  4 omega   67.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 26

  5 omega   49.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 78

  6 omega   84.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 26

  7 omega   51.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   60.0000 26

  8 omega   49.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 89

  9 omega   48.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 57

 10 omega   47.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 45

 11 omega   42.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 26

 12 omega   38.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -150.0000 140

 13 omega   84.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 26

 14 omega   37.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 56

 15 omega   36.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 44

 16 omega   38.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   90.0000 55

 17 omega   38.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 46

 18 omega   38.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 59

 19 omega   -3.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -60.0000 77

 20 omega   32.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -150.0000 78

 21 omega  -18.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000 -180.0000 31

 22 omega   55.00  123.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 68

 23 omega   44.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   72.0000  -34.0000 25

 24 omega   35.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -90.0000 85

 25 omega   42.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  150.0000 67

 26 omega  -12.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   72.0000  -34.0000 39

 27 omega  -15.00   43.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   60.0000 58

 28 omega  -66.00  -30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000 -180.0000 36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1305143000
_diffrn_orient_matrix_UB_12      -0.1324394000
_diffrn_orient_matrix_UB_13      -0.0129710000
_diffrn_orient_matrix_UB_21      -0.0693096000
_diffrn_orient_matrix_UB_22      -0.0071527000
_diffrn_orient_matrix_UB_23      -0.0704607000
_diffrn_orient_matrix_UB_31      0.0821201000
_diffrn_orient_matrix_UB_32      0.1090056000
_diffrn_orient_matrix_UB_33      -0.0518538000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9990
_diffrn_reflns_theta_full        25.61
_diffrn_reflns_theta_max         25.61
_diffrn_reflns_theta_min         2.23
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.915
_refine_diff_density_min         -1.194
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0673
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0649P)^2^+2.7460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1682
_refine_ls_wR_factor_ref         0.1845
_reflns_number_gt                3864
_reflns_number_total             5612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6gc01141a2.cif
_cod_data_source_block           chdq_0307
_cod_depositor_comments          'Adding full bibliography for 7225644.cif.'
_cod_original_cell_volume        1533.97(18)
_cod_database_code               7225644
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C26(H26A,H26B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C30(H30), C31(H31), C33(H33), C34(H34)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C24(H24A,H24B,H24C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4A)
;
_olex2_submission_special_instructions 'No special instructions were received'