#------------------------------------------------------------------------------
#$Date: 2024-02-04 14:16:52 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289566 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/79/7247931.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_7247931
loop_
_publ_author_name
'Zhao, Jianyou'
'Zhang, Jiatai'
'Fang, Pengkai'
'Wu, Jintao'
'Wang, Fan'
'Liu, Zhong-Quan'
_publ_section_title
;
 Electrochemical chlorination of least hindered tertiary and benzylic
 C(sp3)--H bonds
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              507
_journal_page_last               512
_journal_paper_doi               10.1039/D3GC03849A
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H21 Cl O5'
_chemical_formula_sum            'C15 H21 Cl O5'
_chemical_formula_weight         316.77
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc299bdc
_audit_creation_date             2021-10-18
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2021-11-24 deposited with the CCDC.	2023-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.343
_cell_length_b                   9.959
_cell_length_c                   23.828
_cell_measurement_reflns_used    6718
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      53.73
_cell_measurement_theta_min      4.19
_cell_volume                     1505.213
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11099
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.924
_diffrn_reflns_theta_min         4.186
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.594
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.4793
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1314 before and 0.0801 after correction.
The Ratio of minimum to maximum transmission is 0.6386.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 856 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0386
_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)+(0.0492P)²+0.1363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2383
_reflns_number_total             2714
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc03849a2.cif
_cod_data_source_block           20211014li_xiejin_lm2_1_0m
_cod_depositor_comments          'Adding full bibliography for 7247931.cif.'
_cod_original_cell_volume        1505.3
_cod_database_code               7247931
_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.
;
_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 Ternary CH refined with riding coordinates:
 C5(H5), C10(H10), C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C8(H8A,H8B), C12(H12A,H12B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Cl1 Cl 0.29908(15) 0.26467(10) 0.56859(4) 0.0582(3) Uani 1 1 d . . . . .
O1 O 0.0230(3) 0.4644(2) 0.68445(8) 0.0400(5) Uani 1 1 d . . . . .
O2 O 0.2047(4) 0.6174(2) 0.73862(8) 0.0423(5) Uani 1 1 d . . . . .
O3 O 0.3989(3) 0.6146(2) 0.70469(8) 0.0375(5) Uani 1 1 d . . . . .
O4 O 0.0165(3) 0.6506(2) 0.62945(9) 0.0419(6) Uani 1 1 d . . . . .
O5 O -0.0118(4) 0.8421(3) 0.58503(10) 0.0586(7) Uani 1 1 d . . . . .
C1 C -0.0612(6) 0.4898(4) 0.78073(15) 0.0597(10) Uani 1 1 d . . . . .
H1A H -0.154642 0.565359 0.772058 0.090 Uiso 1 1 calc R U . . .
H1B H -0.004093 0.500657 0.818675 0.090 Uiso 1 1 calc R U . . .
H1C H -0.140855 0.405667 0.778564 0.090 Uiso 1 1 calc R U . . .
C2 C 0.1189(5) 0.4863(4) 0.73867(12) 0.0422(8) Uani 1 1 d . . . . .
C3 C 0.2842(6) 0.3787(4) 0.75053(13) 0.0457(8) Uani 1 1 d . . . . .
H3A H 0.219173 0.307253 0.773652 0.055 Uiso 1 1 calc R U . . .
H3B H 0.399647 0.419213 0.772792 0.055 Uiso 1 1 calc R U . . .
C4 C 0.3782(5) 0.3149(3) 0.69779(14) 0.0437(8) Uani 1 1 d . . . . .
H4A H 0.484944 0.248103 0.709574 0.052 Uiso 1 1 calc R U . . .
H4B H 0.264738 0.265623 0.678067 0.052 Uiso 1 1 calc R U . . .
C5 C 0.4812(5) 0.4108(3) 0.65612(12) 0.0350(7) Uani 1 1 d . . . . .
H5 H 0.620524 0.433748 0.673228 0.042 Uiso 1 1 calc R U . . .
C6 C 0.6937(6) 0.2291(4) 0.60751(15) 0.0552(9) Uani 1 1 d . . . . .
H6A H 0.632219 0.160032 0.631826 0.083 Uiso 1 1 calc R U . . .
H6B H 0.822700 0.264045 0.624793 0.083 Uiso 1 1 calc R U . . .
H6C H 0.727552 0.189747 0.570897 0.083 Uiso 1 1 calc R U . . .
C7 C 0.5358(5) 0.3434(3) 0.59974(13) 0.0416(8) Uani 1 1 d . . . . .
C8 C 0.6153(5) 0.4440(3) 0.55684(13) 0.0462(8) Uani 1 1 d . . . . .
H8A H 0.624485 0.399201 0.519839 0.055 Uiso 1 1 calc R U . . .
H8B H 0.759372 0.472358 0.567536 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3641(4) 0.5461(3) 0.65132(11) 0.0319(7) Uani 1 1 d . . . . .
C10 C 0.1298(4) 0.5271(3) 0.64069(12) 0.0355(7) Uani 1 1 d . . . . .
H10 H 0.115128 0.468663 0.606793 0.043 Uiso 1 1 calc R U . . .
C11 C 0.4595(4) 0.6390(3) 0.60755(12) 0.0347(7) Uani 1 1 d . . . . .
H11 H 0.606750 0.658632 0.620122 0.042 Uiso 1 1 calc R U . . .
C12 C 0.4774(5) 0.5683(3) 0.55118(12) 0.0452(8) Uani 1 1 d . . . . .
H12A H 0.539619 0.630161 0.523189 0.054 Uiso 1 1 calc R U . . .
H12B H 0.335351 0.542062 0.537901 0.054 Uiso 1 1 calc R U . . .
C13 C 0.3424(5) 0.7738(3) 0.60652(13) 0.0401(7) Uani 1 1 d . . . . .
H13 H 0.373769 0.817667 0.643343 0.048 Uiso 1 1 calc R U . . .
C14 C 0.1056(5) 0.7592(4) 0.60424(12) 0.0407(7) Uani 1 1 d . . . . .
C15 C 0.4225(6) 0.8707(4) 0.56173(18) 0.0622(11) Uani 1 1 d . . . . .
H15A H 0.575429 0.881384 0.565532 0.093 Uiso 1 1 calc R U . . .
H15B H 0.353805 0.958133 0.566445 0.093 Uiso 1 1 calc R U . . .
H15C H 0.389744 0.834878 0.524430 0.093 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 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
C10 O1 C2 113.4(2) . . ?
C2 O2 O3 107.7(2) . . ?
C9 O3 O2 111.11(19) . . ?
C14 O4 C10 123.4(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 106.1(3) . . ?
O1 C2 C3 110.4(3) . . ?
O2 C2 O1 107.5(2) . . ?
O2 C2 C1 105.6(3) . . ?
O2 C2 C3 112.6(3) . . ?
C1 C2 C3 114.2(3) . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C2 C3 C4 114.0(3) . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C3 C4 H4A 108.2 . . ?
C3 C4 H4B 108.2 . . ?
H4A C4 H4B 107.4 . . ?
C5 C4 C3 116.2(3) . . ?
C5 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
C4 C5 H5 104.8 . . ?
C4 C5 C7 113.0(3) . . ?
C4 C5 C9 112.9(2) . . ?
C7 C5 H5 104.8 . . ?
C7 C5 C9 115.1(2) . . ?
C9 C5 H5 104.8 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
C5 C7 Cl1 110.6(2) . . ?
C6 C7 Cl1 105.4(2) . . ?
C6 C7 C5 111.5(3) . . ?
C8 C7 Cl1 106.2(2) . . ?
C8 C7 C5 112.0(3) . . ?
C8 C7 C6 110.8(3) . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C7 C8 C12 114.0(3) . . ?
H8A C8 H8B 107.7 . . ?
C12 C8 H8A 108.8 . . ?
C12 C8 H8B 108.8 . . ?
O3 C9 C5 105.7(2) . . ?
O3 C9 C10 110.6(2) . . ?
O3 C9 C11 104.7(2) . . ?
C10 C9 C5 112.0(2) . . ?
C10 C9 C11 110.5(2) . . ?
C11 C9 C5 113.0(2) . . ?
O1 C10 O4 106.1(2) . . ?
O1 C10 C9 114.0(2) . . ?
O1 C10 H10 107.4 . . ?
O4 C10 C9 114.2(2) . . ?
O4 C10 H10 107.4 . . ?
C9 C10 H10 107.4 . . ?
C9 C11 H11 106.6 . . ?
C9 C11 C12 110.7(2) . . ?
C9 C11 C13 110.5(2) . . ?
C12 C11 H11 106.6 . . ?
C12 C11 C13 115.3(2) . . ?
C13 C11 H11 106.6 . . ?
C8 C12 H12A 109.7 . . ?
C8 C12 H12B 109.7 . . ?
C11 C12 C8 109.9(2) . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C11 C13 H13 105.8 . . ?
C14 C13 C11 113.4(3) . . ?
C14 C13 H13 105.8 . . ?
C14 C13 C15 111.5(3) . . ?
C15 C13 C11 113.8(3) . . ?
C15 C13 H13 105.8 . . ?
O4 C14 C13 118.3(3) . . ?
O5 C14 O4 117.2(3) . . ?
O5 C14 C13 124.3(3) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
Cl1 C7 1.849(3) . ?
O1 C2 1.444(4) . ?
O1 C10 1.392(4) . ?
O2 O3 1.474(3) . ?
O2 C2 1.414(4) . ?
O3 C9 1.460(3) . ?
O4 C10 1.449(4) . ?
O4 C14 1.360(4) . ?
O5 C14 1.202(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.520(4) . ?
C2 C3 1.526(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.529(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.525(4) . ?
C5 H5 1.0000 . ?
C5 C7 1.541(4) . ?
C5 C9 1.543(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C6 C7 1.528(4) . ?
C7 C8 1.518(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C12 1.522(4) . ?
C9 C10 1.519(4) . ?
C9 C11 1.520(4) . ?
C10 H10 1.0000 . ?
C11 H11 1.0000 . ?
C11 C12 1.521(4) . ?
C11 C13 1.535(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 1.0000 . ?
C13 C14 1.510(4) . ?
C13 C15 1.526(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
Cl1 C7 C8 C12 72.0(3) . . . . ?
O1 C2 C3 C4 25.0(4) . . . . ?
O2 O3 C9 C5 -108.2(2) . . . . ?
O2 O3 C9 C10 13.2(3) . . . . ?
O2 O3 C9 C11 132.2(2) . . . . ?
O2 C2 C3 C4 -95.2(3) . . . . ?
O3 O2 C2 O1 -75.1(3) . . . . ?
O3 O2 C2 C1 172.0(2) . . . . ?
O3 O2 C2 C3 46.7(3) . . . . ?
O3 C9 C10 O1 -53.2(3) . . . . ?
O3 C9 C10 O4 69.1(3) . . . . ?
O3 C9 C11 C12 167.9(2) . . . . ?
O3 C9 C11 C13 -63.1(3) . . . . ?
C1 C2 C3 C4 144.4(3) . . . . ?
C2 O1 C10 O4 -98.8(3) . . . . ?
C2 O1 C10 C9 27.8(3) . . . . ?
C2 O2 O3 C9 47.7(3) . . . . ?
C2 C3 C4 C5 57.0(4) . . . . ?
C3 C4 C5 C7 -169.6(3) . . . . ?
C3 C4 C5 C9 -36.8(4) . . . . ?
C4 C5 C7 Cl1 55.4(3) . . . . ?
C4 C5 C7 C6 -61.5(3) . . . . ?
C4 C5 C7 C8 173.6(3) . . . . ?
C4 C5 C9 O3 69.2(3) . . . . ?
C4 C5 C9 C10 -51.3(3) . . . . ?
C4 C5 C9 C11 -176.9(3) . . . . ?
C5 C7 C8 C12 -48.8(4) . . . . ?
C5 C9 C10 O1 64.4(3) . . . . ?
C5 C9 C10 O4 -173.3(2) . . . . ?
C5 C9 C11 C12 53.4(3) . . . . ?
C5 C9 C11 C13 -177.6(2) . . . . ?
C6 C7 C8 C12 -174.0(3) . . . . ?
C7 C5 C9 O3 -159.0(2) . . . . ?
C7 C5 C9 C10 80.5(3) . . . . ?
C7 C5 C9 C11 -45.1(3) . . . . ?
C7 C8 C12 C11 58.2(3) . . . . ?
C9 C5 C7 Cl1 -76.4(3) . . . . ?
C9 C5 C7 C6 166.7(3) . . . . ?
C9 C5 C7 C8 41.9(3) . . . . ?
C9 C11 C12 C8 -59.4(3) . . . . ?
C9 C11 C13 C14 -48.5(3) . . . . ?
C9 C11 C13 C15 -177.4(3) . . . . ?
C10 O1 C2 O2 34.4(3) . . . . ?
C10 O1 C2 C1 147.0(3) . . . . ?
C10 O1 C2 C3 -88.7(3) . . . . ?
C10 O4 C14 O5 162.6(3) . . . . ?
C10 O4 C14 C13 -22.6(4) . . . . ?
C10 C9 C11 C12 -73.0(3) . . . . ?
C10 C9 C11 C13 56.0(3) . . . . ?
C11 C9 C10 O1 -168.6(2) . . . . ?
C11 C9 C10 O4 -46.3(3) . . . . ?
C11 C13 C14 O4 31.3(4) . . . . ?
C11 C13 C14 O5 -154.2(3) . . . . ?
C12 C11 C13 C14 78.0(3) . . . . ?
C12 C11 C13 C15 -50.9(4) . . . . ?
C13 C11 C12 C8 174.2(3) . . . . ?
C14 O4 C10 O1 156.8(2) . . . . ?
C14 O4 C10 C9 30.3(4) . . . . ?
C15 C13 C14 O4 161.4(3) . . . . ?
C15 C13 C14 O5 -24.2(5) . . . . ?
