#------------------------------------------------------------------------------
#$Date: 2024-10-06 08:21:18 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295111 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/36/7133616.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_7133616
loop_
_publ_author_name
'Zhu, Shaoqun'
'Jia, Lizi'
'Cheng, Qi'
'Han, Ying'
'Sun, Qiu'
'Yu, Huaguang'
'Chen, Xiaoyun'
'Hou, Hong'
_publ_section_title
;
 Dispersion-induced cooperative hydrogen atom transfer for radical
 iodoalkylation.
;
_journal_issue                   77
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10772
_journal_page_last               10775
_journal_paper_doi               10.1039/d4cc03908d
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C16 H16 Cl I O4'
_chemical_formula_sum            'C16 H16 Cl I O4'
_chemical_formula_weight         434.64
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2d42zm
_audit_creation_date             2022-09-21
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-05-23 deposited with the CCDC.	2024-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                93.878(2)
_cell_angle_beta                 97.956(2)
_cell_angle_gamma                110.091(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2223(3)
_cell_length_b                   10.3432(5)
_cell_length_c                   11.0230(6)
_cell_measurement_reflns_used    7700
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.251
_cell_measurement_theta_min      2.649
_cell_volume                     865.22(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13379
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         2.113
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.018
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1062 before and 0.0472 after correction.
The Ratio of minimum to maximum transmission is 0.6770.
The λ/2 correction factor is Not present.
;
_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    1.668
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0373
_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/[σ²(Fo²)+(0.0444P)²+0.8034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3133
_reflns_number_total             3955
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03908d2.cif
_cod_data_source_block           123_a
_cod_depositor_comments          'Adding full bibliography for 7133616.cif.'
_cod_database_code               7133616
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.824
_shelx_estimated_absorpt_t_min   0.779
_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. Rigid body (RIGU) restrains
 C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C14
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C1(H1), C3(H3), C4(H4)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -2.27865(4) -0.04208(3) 0.39327(2) 0.06938(16) Uani 1 1 d . . . . .
Cl1 Cl -1.19357(13) 0.49587(14) 0.44117(12) 0.0843(4) Uani 1 1 d . . . . .
O3 O -2.4813(3) 0.2282(2) -0.0284(2) 0.0540(6) Uani 1 1 d . . . . .
O1 O -2.1680(4) 0.2657(3) -0.1665(2) 0.0643(7) Uani 1 1 d . . . . .
O4 O -2.2861(4) 0.4330(3) 0.0589(3) 0.0706(8) Uani 1 1 d . . . . .
O2 O -2.1883(5) 0.0587(3) -0.1112(3) 0.0900(10) Uani 1 1 d . . . . .
C6 C -1.6790(4) 0.2406(3) 0.3018(3) 0.0457(7) Uani 1 1 d . . . . .
H6 H -1.742688 0.146022 0.295353 0.055 Uiso 1 1 calc R U . . .
C8 C -2.0767(4) 0.1364(3) 0.2124(3) 0.0375(6) Uani 1 1 d . . . . .
H8 H -2.041911 0.058103 0.188029 0.045 Uiso 1 1 calc R U . . .
C5 C -1.7601(4) 0.3282(3) 0.2535(3) 0.0382(6) Uani 1 1 d . . . . .
C11 C -2.0117(4) 0.3261(3) 0.0967(3) 0.0430(7) Uani 1 1 d . . . . .
H11 H -1.951699 0.411212 0.071900 0.052 Uiso 1 1 calc R U . . .
C12 C -2.1954(4) 0.2358(3) 0.0390(3) 0.0390(6) Uani 1 1 d . . . . .
C10 C -2.2487(4) 0.1262(3) 0.1290(3) 0.0479(7) Uani 1 1 d . . . . .
H10A H -2.328798 0.145472 0.178194 0.058 Uiso 1 1 calc R U . . .
H10B H -2.306026 0.034105 0.083809 0.058 Uiso 1 1 calc R U . . .
C13 C -2.3229(4) 0.3132(3) 0.0247(3) 0.0413(6) Uani 1 1 d . . . . .
C7 C -1.9440(4) 0.2718(3) 0.1867(3) 0.0378(6) Uani 1 1 d . . . . .
C9 C -2.0915(5) 0.1433(3) 0.3478(3) 0.0498(7) Uani 1 1 d . . . . .
H9A H -2.125614 0.221508 0.370032 0.060 Uiso 1 1 calc R U . . .
H9B H -1.977046 0.159382 0.396475 0.060 Uiso 1 1 calc R U . . .
C16 C -2.1869(4) 0.1730(4) -0.0878(3) 0.0494(8) Uani 1 1 d . . . . .
C1 C -1.5053(4) 0.2918(4) 0.3590(3) 0.0530(8) Uani 1 1 d . . . . .
H1 H -1.451968 0.232284 0.390642 0.064 Uiso 1 1 calc R U . . .
C3 C -1.4884(5) 0.5208(4) 0.3231(3) 0.0576(9) Uani 1 1 d . . . . .
H3 H -1.423840 0.615355 0.330625 0.069 Uiso 1 1 calc R U . . .
C4 C -1.6616(5) 0.4691(3) 0.2658(3) 0.0494(7) Uani 1 1 d . . . . .
H4 H -1.713627 0.529582 0.234756 0.059 Uiso 1 1 calc R U . . .
C15 C -2.6220(5) 0.2836(4) -0.0415(4) 0.0627(10) Uani 1 1 d . . . . .
H15A H -2.591294 0.361531 -0.087537 0.094 Uiso 1 1 calc R U . . .
H15B H -2.639243 0.312795 0.038748 0.094 Uiso 1 1 calc R U . . .
H15C H -2.728507 0.213171 -0.084363 0.094 Uiso 1 1 calc R U . . .
C2 C -1.4123(4) 0.4313(4) 0.3689(3) 0.0533(8) Uani 1 1 d . . . . .
C14 C -2.1429(9) 0.2246(7) -0.2888(4) 0.1060(19) Uani 1 1 d . . . . .
H14A H -2.125604 0.301168 -0.336377 0.159 Uiso 1 1 calc R U . . .
H14B H -2.244911 0.147786 -0.328793 0.159 Uiso 1 1 calc R U . . .
H14C H -2.041620 0.197720 -0.282251 0.159 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
C13 O3 C15 117.6(3) . . ?
C16 O1 C14 116.9(4) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C1 C6 C5 121.0(3) . . ?
C10 C8 H8 110.3 . . ?
C7 C8 H8 110.3 . . ?
C7 C8 C10 103.3(2) . . ?
C9 C8 H8 110.3 . . ?
C9 C8 C10 112.3(3) . . ?
C9 C8 C7 110.1(2) . . ?
C6 C5 C7 120.7(3) . . ?
C4 C5 C6 118.0(3) . . ?
C4 C5 C7 121.2(3) . . ?
C12 C11 H11 123.6 . . ?
C7 C11 H11 123.6 . . ?
C7 C11 C12 112.8(3) . . ?
C11 C12 C10 103.6(2) . . ?
C11 C12 C13 113.7(2) . . ?
C11 C12 C16 107.2(3) . . ?
C13 C12 C10 110.5(2) . . ?
C13 C12 C16 109.2(2) . . ?
C16 C12 C10 112.7(3) . . ?
C8 C10 C12 106.2(2) . . ?
C8 C10 H10A 110.5 . . ?
C8 C10 H10B 110.5 . . ?
C12 C10 H10A 110.5 . . ?
C12 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
O3 C13 C12 110.5(2) . . ?
O4 C13 O3 124.6(3) . . ?
O4 C13 C12 124.8(3) . . ?
C5 C7 C8 122.2(2) . . ?
C11 C7 C8 111.8(3) . . ?
C11 C7 C5 125.9(3) . . ?
I1 C9 H9A 109.0 . . ?
I1 C9 H9B 109.0 . . ?
C8 C9 I1 113.0(2) . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
O1 C16 C12 110.5(3) . . ?
O2 C16 O1 124.6(3) . . ?
O2 C16 C12 124.8(3) . . ?
C6 C1 H1 120.4 . . ?
C2 C1 C6 119.3(3) . . ?
C2 C1 H1 120.4 . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.1(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.3 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C2 Cl1 119.3(3) . . ?
C1 C2 C3 121.3(3) . . ?
C3 C2 Cl1 119.4(3) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
I1 C9 2.148(3) . ?
Cl1 C2 1.739(3) . ?
O3 C13 1.321(4) . ?
O3 C15 1.452(4) . ?
O1 C16 1.321(4) . ?
O1 C14 1.449(5) . ?
O4 C13 1.190(4) . ?
O2 C16 1.189(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.390(4) . ?
C6 C1 1.380(5) . ?
C8 H8 0.9800 . ?
C8 C10 1.543(4) . ?
C8 C7 1.524(4) . ?
C8 C9 1.514(4) . ?
C5 C7 1.482(4) . ?
C5 C4 1.389(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.498(4) . ?
C11 C7 1.322(4) . ?
C12 C10 1.547(4) . ?
C12 C13 1.520(4) . ?
C12 C16 1.522(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C1 H1 0.9300 . ?
C1 C2 1.370(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(5) . ?
C3 C2 1.370(5) . ?
C4 H4 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C6 C5 C7 C8 27.1(4) . . . . ?
C6 C5 C7 C11 -150.1(3) . . . . ?
C6 C5 C4 C3 0.5(5) . . . . ?
C6 C1 C2 Cl1 179.9(3) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C5 C6 C1 C2 0.4(5) . . . . ?
C11 C12 C10 C8 -15.2(3) . . . . ?
C11 C12 C13 O3 179.0(3) . . . . ?
C11 C12 C13 O4 -2.5(5) . . . . ?
C11 C12 C16 O1 -76.4(3) . . . . ?
C11 C12 C16 O2 100.1(4) . . . . ?
C12 C11 C7 C8 -3.8(4) . . . . ?
C12 C11 C7 C5 173.6(3) . . . . ?
C10 C8 C7 C5 176.3(3) . . . . ?
C10 C8 C7 C11 -6.2(3) . . . . ?
C10 C8 C9 I1 64.6(3) . . . . ?
C10 C12 C13 O3 -65.1(3) . . . . ?
C10 C12 C13 O4 113.5(4) . . . . ?
C10 C12 C16 O1 170.3(3) . . . . ?
C10 C12 C16 O2 -13.1(5) . . . . ?
C13 C12 C10 C8 -137.3(3) . . . . ?
C13 C12 C16 O1 47.1(4) . . . . ?
C13 C12 C16 O2 -136.3(4) . . . . ?
C7 C8 C10 C12 13.2(3) . . . . ?
C7 C8 C9 I1 179.18(19) . . . . ?
C7 C5 C4 C3 -177.1(3) . . . . ?
C7 C11 C12 C10 12.1(4) . . . . ?
C7 C11 C12 C13 132.1(3) . . . . ?
C7 C11 C12 C16 -107.2(3) . . . . ?
C9 C8 C10 C12 131.8(3) . . . . ?
C9 C8 C7 C5 56.2(4) . . . . ?
C9 C8 C7 C11 -126.4(3) . . . . ?
C16 C12 C10 C8 100.3(3) . . . . ?
C16 C12 C13 O3 59.4(3) . . . . ?
C16 C12 C13 O4 -122.1(4) . . . . ?
C1 C6 C5 C7 177.0(3) . . . . ?
C1 C6 C5 C4 -0.7(5) . . . . ?
C4 C5 C7 C8 -155.3(3) . . . . ?
C4 C5 C7 C11 27.5(5) . . . . ?
C4 C3 C2 Cl1 179.9(3) . . . . ?
C4 C3 C2 C1 -0.2(6) . . . . ?
C15 O3 C13 O4 -2.6(5) . . . . ?
C15 O3 C13 C12 175.9(3) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C14 O1 C16 O2 -1.6(6) . . . . ?
C14 O1 C16 C12 174.9(4) . . . . ?
