Selective polychloromethylation and halogenation of alkynes with polyhaloalkanes
Li, Jun-Nan; Li, Zi-Jie; Shen, Liu-Yu; Li, Pinhua; Zhang, Yicheng; Yang, Wen-Chao; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01053D

data_7158802
_publ_section_title
;
 Selective polychloromethylation and halogenation of alkynes with
 polyhaloalkanes
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01053D
_journal_year                    2022
_chemical_formula_moiety         'C21 H13 Br O2'
_chemical_formula_sum            'C21 H13 Br O2'
_chemical_formula_weight         377.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-21 deposited with the CCDC.	2022-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.131(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9293(2)
_cell_length_b                   14.4901(3)
_cell_length_c                   13.4949(4)
_cell_measurement_reflns_used    9162
_cell_measurement_temperature    100.2(7)
_cell_measurement_theta_max      75.3580
_cell_measurement_theta_min      5.2240
_cell_volume                     1649.63(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_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    -93.00 -55.00   0.50    0.05    --  -47.82 -20.00  71.00   76
  2  \w    -23.00   2.00   0.50    0.05    --  -47.82  20.00-121.00   50
  3  \w    -26.00  26.00   0.50    0.05    --   47.82 -20.00  71.00  104
  4  \w     60.00  96.00   0.50    0.05    --   47.82  20.00-121.00   72
  5  \w   -168.00 -88.00   0.50    0.06    -- -102.00 -20.00  71.00  160
  6  \w    103.00 129.00   0.50    0.06    --  104.75  20.00-121.00   52
  7  \w    -24.00  12.00   0.50    0.05    --  -47.82  19.00 -60.00   72
  8  \w   -119.00 -81.00   0.50    0.05    --  -47.82-125.00-180.00   76
  9  \w    -15.00  44.00   0.50    0.05    --   47.82 -37.00 -60.00  118
 10  \w    -69.00 -37.00   0.50    0.06    -- -102.00  61.00 120.00   64
 11  \w   -174.00 -71.00   0.50    0.06    -- -102.00-125.00-120.00  206
 12  \w    -59.00 -33.00   0.50    0.06    -- -102.00  61.00   0.00   52
 13  \w    -93.00 -67.00   0.50    0.06    -- -102.00  77.00 -30.00   52
 14  \w   -174.00 -88.00   0.50    0.06    -- -102.00 -15.00 150.00  172
 15  \w    -66.00 -38.00   0.50    0.06    -- -102.00  61.00-120.00   56
 16  \w     38.00  64.00   0.50    0.06    --  104.75 -61.00 -60.00   52
 17  \w     47.00  73.00   0.50    0.06    --  104.75 -61.00-120.00   52
 18  \w     72.00 106.00   0.50    0.06    --  104.75 -94.00 -90.00   68
 19  \w     40.00  68.00   0.50    0.06    --  104.75 -61.00  90.00   56
 20  \w     32.00  62.00   0.50    0.06    --  104.75 -94.00 -90.00   60
 21  \w     34.00  87.00   0.50    0.06    --  104.75 -94.00-120.00  106
 22  \w     44.00  70.00   0.50    0.06    --  104.75 -61.00 120.00   52
 23  \w     39.00  69.00   0.50    0.06    --  104.75 -61.00 -90.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0300256000
_diffrn_orient_matrix_UB_12      0.1027216000
_diffrn_orient_matrix_UB_13      -0.0289704000
_diffrn_orient_matrix_UB_21      0.1767447000
_diffrn_orient_matrix_UB_22      0.0128004000
_diffrn_orient_matrix_UB_23      0.0131914000
_diffrn_orient_matrix_UB_31      -0.0343490000
_diffrn_orient_matrix_UB_32      -0.0241925000
_diffrn_orient_matrix_UB_33      -0.1165680000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9317
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        65.087
_diffrn_reflns_theta_max         65.087
_diffrn_reflns_theta_min         5.254
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.469
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0265
_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^)+(0.0442P)^2^+0.9643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2624
_reflns_number_total             2702
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01053d2.cif
_cod_data_source_block           20200810a
_cod_database_code               7158802
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C1H1O1Br1N1
_shelx_estimated_absorpt_t_max   0.544
_shelx_estimated_absorpt_t_min   0.478
_diffrn_oxdiff_digest_frames
;
01ab37c4ef0518bea47134135d3b63af12000953df8
;
_diffrn_oxdiff_digest_hkl
;
01fa218f53b535ffa098f9438a751835ebe0ba
;
_reflns_odcompleteness_completeness 95.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              54996
_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 3.516
_oxdiff_exptl_absorpt_empirical_full_min 0.610