#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/77/7127798.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7127798
loop_
_publ_author_name
'Wu, Dan'
'Hao, Wen-Juan'
'Rao, Qian'
'Lu, Yi'
'Tu, Shu-Jiang'
'Jiang, Bo'
_publ_section_title
;
 Engaging 1,7-diynes in a photocatalytic Kharasch-type
 addition/1,5-(SN'')-substitution cascade toward
 β-gem-dihalovinyl carbonyls.
;
_journal_issue                   15
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1911
_journal_page_last               1914
_journal_paper_doi               10.1039/d0cc07880h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C22 H17 Br Cl F2 I O3'
_chemical_formula_weight         609.62
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_audit_update_record
;
2020-11-16 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                99.895(2)
_cell_angle_beta                 92.6680(10)
_cell_angle_gamma                107.318(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0114(8)
_cell_length_b                   10.0086(9)
_cell_length_c                   12.9721(11)
_cell_measurement_reflns_used    2291
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.074
_cell_measurement_theta_min      3.506
_cell_volume                     1094.37(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5588
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    3.449
_exptl_absorpt_correction_T_max  0.4451
_exptl_absorpt_correction_T_min  0.0080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.223
_refine_diff_density_min         -1.971
_refine_diff_density_rms         0.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1247P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1806
_refine_ls_wR_factor_ref         0.1958
_reflns_number_gt                2707
_reflns_number_total             3794
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc07880h2.cif
_cod_data_source_block           191231b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' 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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7127797--7127798.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7127798
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.89743(12) -0.04005(13) 0.21140(8) 0.0835(4) Uani 1 1 d . . .
Cl1 Cl 0.7407(3) 0.0390(3) 0.9228(2) 0.0793(7) Uani 1 1 d . . .
F1 F 1.0123(7) 0.2990(7) 0.6413(5) 0.0906(19) Uani 1 1 d . . .
F2 F 1.0708(6) 0.5177(7) 0.6230(4) 0.0912(19) Uani 1 1 d . . .
I1 I 0.26824(6) 0.22559(7) 0.39598(4) 0.0647(3) Uani 1 1 d . . .
O1 O 0.9208(7) 0.5669(6) 0.8063(4) 0.0592(14) Uani 1 1 d . . .
O2 O 1.0569(8) 0.4220(8) 0.8364(5) 0.0752(18) Uani 1 1 d . . .
O3 O 0.3876(8) 0.5105(7) 0.8098(6) 0.0750(18) Uani 1 1 d . . .
H3 H 0.3094 0.4460 0.8159 0.112 Uiso 1 1 calc R . .
C1 C 0.9867(9) 0.4668(9) 0.7792(6) 0.0529(19) Uani 1 1 d . . .
C2 C 0.9628(9) 0.4164(10) 0.6605(6) 0.055(2) Uani 1 1 d . . .
C3 C 0.8084(9) 0.3889(8) 0.6037(6) 0.0483(17) Uani 1 1 d . . .
H3A H 0.8073 0.4142 0.5380 0.058 Uiso 1 1 calc R . .
C4 C 0.6704(7) 0.3316(7) 0.6365(5) 0.0370(14) Uani 1 1 d . . .
C5 C 0.5234(8) 0.3162(7) 0.5751(5) 0.0428(16) Uani 1 1 d . . .
C6 C 0.4133(9) 0.3788(8) 0.6383(6) 0.0517(18) Uani 1 1 d . . .
H6A H 0.3183 0.3031 0.6422 0.062 Uiso 1 1 calc R . .
H6B H 0.3853 0.4468 0.6026 0.062 Uiso 1 1 calc R . .
C7 C 0.4879(10) 0.4533(9) 0.7496(6) 0.0512(18) Uani 1 1 d . . .
H7 H 0.5791 0.5332 0.7431 0.061 Uiso 1 1 calc R . .
C8 C 0.5466(8) 0.3511(8) 0.7988(6) 0.0446(16) Uani 1 1 d . . .
C9 C 0.6437(8) 0.2894(7) 0.7396(5) 0.0413(15) Uani 1 1 d . . .
C10 C 0.7031(8) 0.1934(8) 0.7781(6) 0.0465(17) Uani 1 1 d . . .
H10 H 0.7664 0.1508 0.7387 0.056 Uiso 1 1 calc R . .
C11 C 0.6687(10) 0.1610(9) 0.8746(6) 0.0543(19) Uani 1 1 d . . .
C12 C 0.5753(10) 0.2231(10) 0.9340(7) 0.062(2) Uani 1 1 d . . .
H12 H 0.5526 0.2003 0.9992 0.074 Uiso 1 1 calc R . .
C13 C 0.5159(10) 0.3185(9) 0.8965(6) 0.058(2) Uani 1 1 d . . .
H13 H 0.4544 0.3618 0.9371 0.070 Uiso 1 1 calc R . .
C14 C 0.4900(8) 0.2495(7) 0.4750(6) 0.0452(16) Uani 1 1 d . . .
C15 C 0.5840(8) 0.1785(7) 0.4092(5) 0.0400(15) Uani 1 1 d . . .
C16 C 0.6599(9) 0.0921(8) 0.4503(6) 0.0469(17) Uani 1 1 d . . .
H16 H 0.6479 0.0782 0.5189 0.056 Uiso 1 1 calc R . .
C17 C 0.7520(10) 0.0274(8) 0.3909(7) 0.0548(19) Uani 1 1 d . . .
H17 H 0.8001 -0.0308 0.4186 0.066 Uiso 1 1 calc R . .
C18 C 0.7712(9) 0.0502(9) 0.2915(6) 0.0526(19) Uani 1 1 d . . .
C19 C 0.6999(11) 0.1325(10) 0.2480(7) 0.064(2) Uani 1 1 d . . .
H19 H 0.7137 0.1457 0.1794 0.077 Uiso 1 1 calc R . .
C20 C 0.6063(9) 0.1966(9) 0.3075(6) 0.0541(19) Uani 1 1 d . . .
H20 H 0.5575 0.2530 0.2779 0.065 Uiso 1 1 calc R . .
C21 C 0.9341(15) 0.6252(12) 0.9189(7) 0.088(3) Uani 1 1 d . . .
H21A H 0.8949 0.5486 0.9570 0.105 Uiso 1 1 calc R . .
H21B H 1.0427 0.6746 0.9450 0.105 Uiso 1 1 calc R . .
C22 C 0.8433(16) 0.7236(13) 0.9348(9) 0.107(4) Uani 1 1 d . . .
H22A H 0.8805 0.7972 0.8949 0.160 Uiso 1 1 calc R . .
H22B H 0.8542 0.7658 1.0081 0.160 Uiso 1 1 calc R . .
H22C H 0.7352 0.6730 0.9118 0.160 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C21 116.1(7) . . ?
C7 O3 H3 109.5 . . ?
O2 C1 O1 126.4(7) . . ?
O2 C1 C2 123.5(8) . . ?
O1 C1 C2 110.1(7) . . ?
F2 C2 F1 104.5(7) . . ?
F2 C2 C3 109.6(7) . . ?
F1 C2 C3 111.2(7) . . ?
F2 C2 C1 104.9(6) . . ?
F1 C2 C1 105.9(7) . . ?
C3 C2 C1 119.6(6) . . ?
C4 C3 C2 126.7(7) . . ?
C4 C3 H3A 116.6 . . ?
C2 C3 H3A 116.6 . . ?
C3 C4 C5 121.8(6) . . ?
C3 C4 C9 126.1(6) . . ?
C5 C4 C9 111.8(6) . . ?
C14 C5 C4 122.3(6) . . ?
C14 C5 C6 124.3(7) . . ?
C4 C5 C6 113.4(6) . . ?
C5 C6 C7 111.7(6) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
O3 C7 C8 113.7(6) . . ?
O3 C7 C6 112.7(7) . . ?
C8 C7 C6 108.3(6) . . ?
O3 C7 H7 107.3 . . ?
C8 C7 H7 107.3 . . ?
C6 C7 H7 107.3 . . ?
C13 C8 C9 119.4(7) . . ?
C13 C8 C7 125.4(7) . . ?
C9 C8 C7 115.2(6) . . ?
C10 C9 C8 119.5(6) . . ?
C10 C9 C4 125.0(6) . . ?
C8 C9 C4 115.4(6) . . ?
C11 C10 C9 119.9(7) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.8(7) . . ?
C10 C11 Cl1 120.2(6) . . ?
C12 C11 Cl1 119.0(6) . . ?
C13 C12 C11 119.7(7) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 120.6(7) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C5 C14 C15 128.4(7) . . ?
C5 C14 I1 118.9(5) . . ?
C15 C14 I1 112.7(5) . . ?
C20 C15 C16 117.1(7) . . ?
C20 C15 C14 122.5(6) . . ?
C16 C15 C14 120.3(6) . . ?
C17 C16 C15 121.4(7) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 119.0(8) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C19 C18 C17 121.9(8) . . ?
C19 C18 Br1 119.9(6) . . ?
C17 C18 Br1 118.2(6) . . ?
C18 C19 C20 119.1(8) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C15 C20 C19 121.5(7) . . ?
C15 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C22 C21 O1 108.4(9) . . ?
C22 C21 H21A 110.0 . . ?
O1 C21 H21A 110.0 . . ?
C22 C21 H21B 110.0 . . ?
O1 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.894(8) . ?
Cl1 C11 1.732(8) . ?
F1 C2 1.365(10) . ?
F2 C2 1.356(10) . ?
I1 C14 2.131(7) . ?
O1 C1 1.317(10) . ?
O1 C21 1.462(10) . ?
O2 C1 1.180(10) . ?
O3 C7 1.405(9) . ?
O3 H3 0.8200 . ?
C1 C2 1.519(10) . ?
C2 C3 1.470(11) . ?
C3 C4 1.328(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.466(9) . ?
C4 C9 1.480(9) . ?
C5 C14 1.329(10) . ?
C5 C6 1.523(10) . ?
C6 C7 1.527(11) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.500(11) . ?
C7 H7 0.9800 . ?
C8 C13 1.382(10) . ?
C8 C9 1.399(9) . ?
C9 C10 1.380(10) . ?
C10 C11 1.373(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(12) . ?
C12 C13 1.369(12) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.473(10) . ?
C15 C20 1.379(10) . ?
C15 C16 1.405(10) . ?
C16 C17 1.382(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.359(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.360(12) . ?
C19 C20 1.390(12) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.452(16) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 O1 C1 O2 -1.4(13) . . . . ?
C21 O1 C1 C2 179.7(8) . . . . ?
O2 C1 C2 F2 -99.8(10) . . . . ?
O1 C1 C2 F2 79.1(8) . . . . ?
O2 C1 C2 F1 10.4(11) . . . . ?
O1 C1 C2 F1 -170.7(7) . . . . ?
O2 C1 C2 C3 136.8(9) . . . . ?
O1 C1 C2 C3 -44.3(10) . . . . ?
F2 C2 C3 C4 -158.5(8) . . . . ?
F1 C2 C3 C4 86.5(9) . . . . ?
C1 C2 C3 C4 -37.5(12) . . . . ?
C2 C3 C4 C5 176.7(7) . . . . ?
C2 C3 C4 C9 2.9(12) . . . . ?
C3 C4 C5 C14 54.4(10) . . . . ?
C9 C4 C5 C14 -131.0(7) . . . . ?
C3 C4 C5 C6 -127.7(7) . . . . ?
C9 C4 C5 C6 46.9(8) . . . . ?
C14 C5 C6 C7 -177.9(7) . . . . ?
C4 C5 C6 C7 4.2(9) . . . . ?
C5 C6 C7 O3 -179.3(6) . . . . ?
C5 C6 C7 C8 -52.6(8) . . . . ?
O3 C7 C8 C13 -3.5(12) . . . . ?
C6 C7 C8 C13 -129.6(8) . . . . ?
O3 C7 C8 C9 178.5(7) . . . . ?
C6 C7 C8 C9 52.4(9) . . . . ?
C13 C8 C9 C10 2.1(11) . . . . ?
C7 C8 C9 C10 -179.7(7) . . . . ?
C13 C8 C9 C4 -179.6(7) . . . . ?
C7 C8 C9 C4 -1.4(9) . . . . ?
C3 C4 C9 C10 -57.6(11) . . . . ?
C5 C4 C9 C10 128.1(7) . . . . ?
C3 C4 C9 C8 124.2(8) . . . . ?
C5 C4 C9 C8 -50.1(8) . . . . ?
C8 C9 C10 C11 -1.0(11) . . . . ?
C4 C9 C10 C11 -179.1(7) . . . . ?
C9 C10 C11 C12 0.0(12) . . . . ?
C9 C10 C11 Cl1 179.2(6) . . . . ?
C10 C11 C12 C13 0.0(13) . . . . ?
Cl1 C11 C12 C13 -179.2(7) . . . . ?
C11 C12 C13 C8 1.2(14) . . . . ?
C9 C8 C13 C12 -2.2(13) . . . . ?
C7 C8 C13 C12 179.9(8) . . . . ?
C4 C5 C14 C15 1.5(11) . . . . ?
C6 C5 C14 C15 -176.2(7) . . . . ?
C4 C5 C14 I1 177.3(5) . . . . ?
C6 C5 C14 I1 -0.4(10) . . . . ?
C5 C14 C15 C20 -135.1(8) . . . . ?
I1 C14 C15 C20 48.9(8) . . . . ?
C5 C14 C15 C16 42.6(11) . . . . ?
I1 C14 C15 C16 -133.3(6) . . . . ?
C20 C15 C16 C17 -0.4(11) . . . . ?
C14 C15 C16 C17 -178.3(7) . . . . ?
C15 C16 C17 C18 1.1(12) . . . . ?
C16 C17 C18 C19 -1.3(13) . . . . ?
C16 C17 C18 Br1 -179.8(6) . . . . ?
C17 C18 C19 C20 0.8(13) . . . . ?
Br1 C18 C19 C20 179.3(6) . . . . ?
C16 C15 C20 C19 -0.1(12) . . . . ?
C14 C15 C20 C19 177.7(7) . . . . ?
C18 C19 C20 C15 -0.1(13) . . . . ?
C1 O1 C21 C22 -174.8(9) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352503
