#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:21:05 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286179 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/94/7159495.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_7159495
loop_
_publ_author_name
'Yuan, Peng'
'Liu, Rui'
'Zhu, Hui-Min'
'Liao, Zhixin'
'Xiang, Jia-Chen'
'Wu, An-Xin'
_publ_section_title
;
 An I₂-DMSO catalytic manifold enabled aromatization for C-ring
 editing of podophyllotoxone.
;
_journal_issue                   32
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6468
_journal_page_last               6473
_journal_paper_doi               10.1039/d3ob00927k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C28 H22 Cl N O7, C H Cl3'
_chemical_formula_sum            'C29 H23 Cl4 N O7'
_chemical_formula_weight         639.28
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-05-11 deposited with the CCDC.	2023-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                110.796(2)
_cell_angle_beta                 90.433(2)
_cell_angle_gamma                91.711(2)
_cell_formula_units_Z            1
_cell_length_a                   5.7924(3)
_cell_length_b                   11.1413(5)
_cell_length_c                   12.0240(6)
_cell_measurement_reflns_used    7438
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.54
_cell_measurement_theta_min      3.10
_cell_volume                     724.95(6)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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_temperature      150.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_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            18929
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.003
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_min         2.143
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.456
_exptl_absorpt_correction_T_max  0.0277
_exptl_absorpt_correction_T_min  0.0110
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0780 before and 0.0643 after correction.
The Ratio of minimum to maximum transmission is 0.3971.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1904 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5060
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0894P)²+0.0290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1408
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4393
_reflns_number_total             5060
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00927k2.cif
_cod_data_source_block           mo_0428_2_0m
_cod_depositor_comments
'Adding full bibliography for 7159495--7159496.cif.'
_cod_database_code               7159495
_shelx_shelxl_version_number     2014/7
_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   0.969
_shelx_estimated_absorpt_t_min   0.952
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C4(H4), C5(H5), C14(H14), C18(H18), C21(H21), C25(H25)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'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
Cl1 Cl 0.3211(3) 1.18942(15) 0.94834(14) 0.0468(4) Uani 1 1 d . . . . .
O1 O 0.8698(7) 0.5850(4) 0.5600(4) 0.0340(9) Uani 1 1 d . . . . .
O2 O 0.8071(7) 0.3735(4) 0.5072(4) 0.0363(9) Uani 1 1 d . . . . .
O3 O -0.2648(7) 0.6231(4) 0.1415(4) 0.0400(10) Uani 1 1 d . . . . .
O4 O -0.2431(7) 0.4019(4) 0.0782(4) 0.0367(10) Uani 1 1 d . . . . .
O5 O 0.1014(7) 0.0089(4) 0.3682(4) 0.0331(9) Uani 1 1 d . . . . .
O6 O 0.4026(7) -0.1206(3) 0.2115(3) 0.0308(9) Uani 1 1 d . . . . .
O7 O 0.6916(7) -0.0050(4) 0.1052(4) 0.0387(10) Uani 1 1 d . . . . .
N1 N 0.4012(9) 0.8309(5) 0.4526(4) 0.0342(11) Uani 1 1 d . . . . .
H1 H 0.4172 0.8650 0.3972 0.041 Uiso 1 1 calc R . . . .
C1 C 0.3168(9) 0.8690(5) 0.6609(5) 0.0303(12) Uani 1 1 d . . . . .
H1A H 0.2856 0.7798 0.6429 0.036 Uiso 1 1 calc R . . . .
C2 C 0.2993(10) 0.9515(6) 0.7755(5) 0.0352(13) Uani 1 1 d . . . . .
H2 H 0.2566 0.9200 0.8365 0.042 Uiso 1 1 calc R . . . .
C3 C 0.3450(11) 1.0834(6) 0.8025(5) 0.0367(13) Uani 1 1 d . . . . .
C4 C 0.4051(11) 1.1290(5) 0.7141(6) 0.0350(13) Uani 1 1 d . . . . .
H4 H 0.4349 1.2184 0.7327 0.042 Uiso 1 1 calc R . . . .
C5 C 0.4222(10) 1.0448(5) 0.5979(5) 0.0309(12) Uani 1 1 d . . . . .
H5 H 0.4633 1.0767 0.5369 0.037 Uiso 1 1 calc R . . . .
C6 C 0.3793(9) 0.9127(5) 0.5696(5) 0.0268(11) Uani 1 1 d . . . . .
C7 C 0.3992(9) 0.6963(5) 0.4179(5) 0.0254(11) Uani 1 1 d . . . . .
C8 C 0.5596(9) 0.6376(5) 0.4634(5) 0.0281(12) Uani 1 1 d . . . . .
C9 C 0.7581(10) 0.6948(5) 0.5475(5) 0.0326(13) Uani 1 1 d . . . . .
H9A H 0.8657 0.7438 0.5146 0.039 Uiso 1 1 calc R . . . .
H9B H 0.7033 0.7528 0.6252 0.039 Uiso 1 1 calc R . . . .
C10 C 0.7511(10) 0.4738(6) 0.4993(5) 0.0311(12) Uani 1 1 d . . . . .
C11 C 0.5595(9) 0.5034(5) 0.4314(5) 0.0270(11) Uani 1 1 d . . . . .
C12 C 0.4050(9) 0.4206(5) 0.3496(5) 0.0265(11) Uani 1 1 d . . . . .
C13 C 0.2412(9) 0.4795(5) 0.2975(5) 0.0258(11) Uani 1 1 d . . . . .
C14 C 0.0784(10) 0.3998(5) 0.2085(5) 0.0282(12) Uani 1 1 d . . . . .
H14 H 0.0805 0.3088 0.1828 0.034 Uiso 1 1 calc R . . . .
C15 C -0.0756(9) 0.4581(6) 0.1635(5) 0.0295(12) Uani 1 1 d . . . . .
C16 C -0.3771(10) 0.5046(6) 0.0686(6) 0.0352(13) Uani 1 1 d . . . . .
H16A H -0.3857 0.4997 -0.0152 0.042 Uiso 1 1 calc R . . . .
H16B H -0.5361 0.4985 0.0962 0.042 Uiso 1 1 calc R . . . .
C17 C -0.0883(10) 0.5927(6) 0.2012(5) 0.0314(13) Uani 1 1 d . . . . .
C18 C 0.0593(10) 0.6724(5) 0.2835(5) 0.0282(12) Uani 1 1 d . . . . .
H18 H 0.0481 0.7630 0.3078 0.034 Uiso 1 1 calc R . . . .
C19 C 0.2330(9) 0.6171(5) 0.3331(5) 0.0252(11) Uani 1 1 d . . . . .
C20 C 0.4065(9) 0.2770(5) 0.3132(5) 0.0248(11) Uani 1 1 d . . . . .
C21 C 0.2497(10) 0.2149(5) 0.3634(5) 0.0291(12) Uani 1 1 d . . . . .
H21 H 0.1460 0.2631 0.4220 0.035 Uiso 1 1 calc R . . . .
C22 C 0.2462(10) 0.0811(5) 0.3269(5) 0.0281(12) Uani 1 1 d . . . . .
C23 C 0.4027(10) 0.0107(5) 0.2417(5) 0.0271(11) Uani 1 1 d . . . . .
C24 C 0.5550(10) 0.0738(5) 0.1914(5) 0.0309(12) Uani 1 1 d . . . . .
C25 C 0.5596(9) 0.2069(5) 0.2274(5) 0.0288(12) Uani 1 1 d . . . . .
H25 H 0.6666 0.2500 0.1938 0.035 Uiso 1 1 calc R . . . .
C26 C 0.8594(11) 0.0536(6) 0.0531(6) 0.0404(15) Uani 1 1 d . . . . .
H26A H 0.9312 -0.0126 -0.0133 0.061 Uiso 1 1 calc GR . . . .
H26B H 0.9780 0.0992 0.1130 0.061 Uiso 1 1 calc GR . . . .
H26C H 0.7844 0.1146 0.0238 0.061 Uiso 1 1 calc GR . . . .
C27 C 0.2878(13) -0.1894(5) 0.1013(6) 0.0406(15) Uani 1 1 d . . . . .
H27A H 0.3660 -0.1706 0.0371 0.061 Uiso 1 1 calc GR . . . .
H27B H 0.1271 -0.1634 0.1047 0.061 Uiso 1 1 calc GR . . . .
H27C H 0.2910 -0.2818 0.0861 0.061 Uiso 1 1 calc GR . . . .
C28 C -0.0713(11) 0.0729(6) 0.4498(7) 0.0434(16) Uani 1 1 d . . . . .
H28A H -0.1763 0.1141 0.4112 0.065 Uiso 1 1 calc GR . . . .
H28B H 0.0025 0.1383 0.5197 0.065 Uiso 1 1 calc GR . . . .
H28C H -0.1587 0.0104 0.4747 0.065 Uiso 1 1 calc GR . . . .
Cl2 Cl 0.3781(4) 0.5625(4) 0.7588(3) 0.0979(10) Uani 1 1 d . . . . .
Cl3 Cl 0.0583(4) 0.4193(2) 0.8501(2) 0.0765(7) Uani 1 1 d . . . . .
Cl4 Cl -0.0570(4) 0.66809(19) 0.84940(18) 0.0635(6) Uani 1 1 d . . . . .
C29 C 0.0841(13) 0.5235(8) 0.7719(7) 0.0548(19) Uani 1 1 d . . . . .
H29 H 0.0121 0.4822 0.6908 0.066 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C10 O1 C9 111.2(4) . . ?
C17 O3 C16 107.0(4) . . ?
C15 O4 C16 106.4(4) . . ?
C22 O5 C28 118.0(4) . . ?
C23 O6 C27 113.7(4) . . ?
C24 O7 C26 117.8(4) . . ?
C6 N1 H1 118.3 . . ?
C6 N1 C7 123.3(5) . . ?
C7 N1 H1 118.3 . . ?
C2 C1 H1A 119.3 . . ?
C2 C1 C6 121.4(5) . . ?
C6 C1 H1A 119.3 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(5) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 Cl1 119.7(5) . . ?
C4 C3 Cl1 120.0(5) . . ?
C4 C3 C2 120.3(6) . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(5) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(5) . . ?
C6 C5 H5 119.8 . . ?
N1 C6 C1 122.8(5) . . ?
N1 C6 C5 118.8(5) . . ?
C1 C6 C5 118.4(5) . . ?
N1 C7 C19 121.1(5) . . ?
C8 C7 N1 120.6(5) . . ?
C8 C7 C19 118.2(5) . . ?
C7 C8 C9 129.8(5) . . ?
C7 C8 C11 121.7(5) . . ?
C11 C8 C9 108.4(5) . . ?
O1 C9 C8 104.5(4) . . ?
O1 C9 H9A 110.8 . . ?
O1 C9 H9B 110.8 . . ?
C8 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
O1 C10 C11 108.3(5) . . ?
O2 C10 O1 120.6(5) . . ?
O2 C10 C11 131.1(6) . . ?
C8 C11 C10 107.3(5) . . ?
C12 C11 C8 123.3(5) . . ?
C12 C11 C10 129.4(5) . . ?
C11 C12 C13 115.9(5) . . ?
C11 C12 C20 123.7(5) . . ?
C13 C12 C20 120.4(5) . . ?
C12 C13 C14 119.5(5) . . ?
C12 C13 C19 121.3(5) . . ?
C19 C13 C14 119.2(5) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 C13 117.9(5) . . ?
C15 C14 H14 121.0 . . ?
O4 C15 C17 109.4(5) . . ?
C14 C15 O4 127.7(5) . . ?
C14 C15 C17 122.8(5) . . ?
O3 C16 O4 107.4(4) . . ?
O3 C16 H16A 110.2 . . ?
O3 C16 H16B 110.2 . . ?
O4 C16 H16A 110.2 . . ?
O4 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
O3 C17 C15 109.3(5) . . ?
C18 C17 O3 128.5(5) . . ?
C18 C17 C15 122.1(5) . . ?
C17 C18 H18 120.9 . . ?
C17 C18 C19 118.2(5) . . ?
C19 C18 H18 120.9 . . ?
C7 C19 C13 119.4(5) . . ?
C18 C19 C7 120.9(5) . . ?
C18 C19 C13 119.7(5) . . ?
C21 C20 C12 119.4(5) . . ?
C21 C20 C25 120.6(5) . . ?
C25 C20 C12 120.0(5) . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.4(5) . . ?
C22 C21 H21 120.3 . . ?
O5 C22 C21 125.2(5) . . ?
O5 C22 C23 114.8(5) . . ?
C21 C22 C23 119.9(5) . . ?
O6 C23 C22 118.7(5) . . ?
O6 C23 C24 121.4(5) . . ?
C24 C23 C22 119.9(5) . . ?
O7 C24 C23 114.8(5) . . ?
O7 C24 C25 124.8(5) . . ?
C23 C24 C25 120.4(5) . . ?
C20 C25 H25 120.1 . . ?
C24 C25 C20 119.7(5) . . ?
C24 C25 H25 120.1 . . ?
O7 C26 H26A 109.5 . . ?
O7 C26 H26B 109.5 . . ?
O7 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O6 C27 H27A 109.5 . . ?
O6 C27 H27B 109.5 . . ?
O6 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O5 C28 H28A 109.5 . . ?
O5 C28 H28B 109.5 . . ?
O5 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
Cl2 C29 Cl4 108.1(5) . . ?
Cl2 C29 H29 109.5 . . ?
Cl3 C29 Cl2 110.4(4) . . ?
Cl3 C29 Cl4 109.7(4) . . ?
Cl3 C29 H29 109.5 . . ?
Cl4 C29 H29 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 C3 1.741(6) . ?
O1 C9 1.454(7) . ?
O1 C10 1.357(7) . ?
O2 C10 1.208(7) . ?
O3 C16 1.433(8) . ?
O3 C17 1.363(7) . ?
O4 C15 1.370(7) . ?
O4 C16 1.439(7) . ?
O5 C22 1.359(7) . ?
O5 C28 1.426(7) . ?
O6 C23 1.376(6) . ?
O6 C27 1.422(8) . ?
O7 C24 1.371(7) . ?
O7 C26 1.423(7) . ?
N1 H1 0.8800 . ?
N1 C6 1.388(7) . ?
N1 C7 1.407(7) . ?
C1 H1A 0.9500 . ?
C1 C2 1.365(8) . ?
C1 C6 1.396(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.404(9) . ?
C3 C4 1.374(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(8) . ?
C7 C8 1.368(8) . ?
C7 C19 1.428(8) . ?
C8 C9 1.494(8) . ?
C8 C11 1.405(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.485(8) . ?
C11 C12 1.383(8) . ?
C12 C13 1.429(7) . ?
C12 C20 1.501(7) . ?
C13 C14 1.443(8) . ?
C13 C19 1.440(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.338(8) . ?
C15 C17 1.408(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.349(9) . ?
C18 H18 0.9500 . ?
C18 C19 1.427(8) . ?
C20 C21 1.391(8) . ?
C20 C25 1.394(8) . ?
C21 H21 0.9500 . ?
C21 C22 1.397(8) . ?
C22 C23 1.404(8) . ?
C23 C24 1.383(8) . ?
C24 C25 1.388(8) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
Cl2 C29 1.767(8) . ?
Cl3 C29 1.738(8) . ?
Cl4 C29 1.776(8) . ?
C29 H29 1.0000 . ?
