#------------------------------------------------------------------------------
#$Date: 2022-06-06 04:48:15 +0300 (Mon, 06 Jun 2022) $
#$Revision: 275788 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/48/7244844.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_7244844
loop_
_publ_author_name
'Zhang, Yan'
'Ma, Chanchan'
'Cai, Zhenzhi'
'Struwe, Julia'
'Chen, Shengjie'
'Xu, Jinming'
'Li, Shiyin'
'Zeng, Wangyu'
'Ackermann, Lutz'
_publ_section_title
;
 Electrooxidative tricyclic 6--7--6 fused-system domino assembly to
 allocolchicines by a removable radical strategy
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              3697
_journal_page_last               3703
_journal_paper_doi               10.1039/D2GC00684G
_journal_volume                  24
_journal_year                    2022
_chemical_formula_sum            'C24 H17 F3 O3'
_chemical_formula_weight         410.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-11-28 deposited with the CCDC.	2022-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 129.048(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.313(3)
_cell_length_b                   13.516(3)
_cell_length_c                   15.514(3)
_cell_measurement_reflns_used    2164
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.61
_cell_volume                     2005.1(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_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  0.1305
_diffrn_reflns_av_unetI/netI     0.1002
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15432
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         2.264
_exptl_absorpt_coefficient_mu    0.107
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          .32
_exptl_crystal_size_mid          .32
_exptl_crystal_size_min          .29
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1581
_refine_ls_R_factor_gt           0.0822
_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)+(0.1107P)²+0.7228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2011
_refine_ls_wR_factor_ref         0.2610
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2315
_reflns_number_total             4537
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc00684g2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7244844--7244845.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7244844
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
F1 F -0.3797(6) -0.5573(2) 0.2029(4) 0.170(2) Uani 1 1 d . . . . .
F2 F -0.2858(3) -0.5283(2) 0.3671(2) 0.1295(14) Uani 1 1 d . . . . .
F3 F -0.4927(3) -0.4908(2) 0.2441(3) 0.1263(12) Uani 1 1 d . . . . .
O1 O -0.0778(3) -0.4233(2) 0.3608(3) 0.0868(9) Uani 1 1 d . . . . .
O2 O -0.2061(3) 0.06164(19) 0.2044(2) 0.0796(9) Uani 1 1 d . . . . .
O3 O -0.4512(3) -0.23913(19) 0.00786(19) 0.0678(8) Uani 1 1 d . . . . .
C1 C -0.0669(4) -0.3372(3) 0.5457(3) 0.0736(12) Uani 1 1 d . . . . .
H1A H -0.0267 -0.3998 0.5660 0.088 Uiso 1 1 calc R U . . .
C2 C -0.0539(5) -0.2764(4) 0.6233(3) 0.0919(16) Uani 1 1 d . . . . .
H2A H -0.0069 -0.2986 0.6956 0.110 Uiso 1 1 calc R U . . .
C3 C -0.1109(5) -0.1830(4) 0.5932(3) 0.0874(14) Uani 1 1 d . . . . .
H3A H -0.1022 -0.1424 0.6456 0.105 Uiso 1 1 calc R U . . .
C4 C -0.1802(4) -0.1485(3) 0.4872(3) 0.0702(11) Uani 1 1 d . . . . .
H4A H -0.2166 -0.0846 0.4689 0.084 Uiso 1 1 calc R U . . .
C5 C -0.1966(3) -0.2087(3) 0.4063(3) 0.0524(8) Uani 1 1 d . . . . .
C6 C -0.1405(3) -0.3044(3) 0.4368(3) 0.0555(9) Uani 1 1 d . . . . .
C7 C -0.1672(4) -0.3760(3) 0.3525(3) 0.0587(9) Uani 1 1 d . . . . .
C8 C -0.3209(4) -0.3928(2) 0.2598(3) 0.0511(8) Uani 1 1 d . . . . .
C9 C -0.4025(3) -0.3210(2) 0.1877(2) 0.0457(8) Uani 1 1 d . . . . .
C10 C -0.3433(3) -0.2227(2) 0.1954(2) 0.0458(8) Uani 1 1 d . . . . .
C11 C -0.2565(3) -0.1677(2) 0.2952(3) 0.0492(8) Uani 1 1 d . . . . .
C12 C -0.5584(3) -0.3320(2) 0.1010(2) 0.0476(8) Uani 1 1 d . . . . .
C13 C -0.6187(4) -0.3958(3) 0.0121(3) 0.0718(11) Uani 1 1 d . . . . .
H13A H -0.5627 -0.4327 0.0030 0.086 Uiso 1 1 calc R U . . .
C14 C -0.7647(6) -0.4048(4) -0.0646(4) 0.0895(16) Uani 1 1 d . . . . .
H14A H -0.8060 -0.4462 -0.1258 0.107 Uiso 1 1 calc R U . . .
C15 C -0.8455(5) -0.3529(4) -0.0491(4) 0.0917(16) Uani 1 1 d . . . . .
H15A H -0.9420 -0.3612 -0.0983 0.110 Uiso 1 1 calc R U . . .
C16 C -0.7872(5) -0.2891(4) 0.0372(4) 0.0922(15) Uani 1 1 d . . . . .
H16A H -0.8437 -0.2535 0.0466 0.111 Uiso 1 1 calc R U . . .
C17 C -0.6430(4) -0.2771(3) 0.1115(3) 0.0643(10) Uani 1 1 d . . . . .
H17A H -0.6036 -0.2313 0.1688 0.077 Uiso 1 1 calc R U . . .
C18 C -0.2161(4) -0.0719(2) 0.2929(3) 0.0559(9) Uani 1 1 d . . . . .
H18A H -0.1624 -0.0349 0.3580 0.067 Uiso 1 1 calc R U . . .
C19 C -0.2548(4) -0.0315(3) 0.1957(3) 0.0575(9) Uani 1 1 d . . . . .
C20 C -0.3338(4) -0.0857(3) 0.0981(3) 0.0574(9) Uani 1 1 d . . . . .
H20A H -0.3573 -0.0592 0.0330 0.069 Uiso 1 1 calc R U . . .
C21 C -0.3769(3) -0.1794(2) 0.0991(3) 0.0518(8) Uani 1 1 d . . . . .
C22 C -0.3695(4) -0.4912(3) 0.2663(3) 0.0646(10) Uani 1 1 d . . . . .
C23 C -0.4874(5) -0.2045(3) -0.0942(3) 0.0792(13) Uani 1 1 d . . . . .
H23A H -0.5463 -0.2523 -0.1516 0.119 Uiso 1 1 calc R U . . .
H23B H -0.4038 -0.1952 -0.0858 0.119 Uiso 1 1 calc R U . . .
H23C H -0.5364 -0.1427 -0.1140 0.119 Uiso 1 1 calc R U . . .
C24 C -0.2237(5) 0.1036(4) 0.1120(4) 0.0884(14) Uani 1 1 d . . . . .
H24A H -0.1876 0.1699 0.1297 0.133 Uiso 1 1 calc R U . . .
H24B H -0.3214 0.1048 0.0488 0.133 Uiso 1 1 calc R U . . .
H24C H -0.1741 0.0645 0.0952 0.133 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'
F F 0.0171 0.0103 '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
C19 O2 C24 119.2(3) . . ?
C21 O3 C23 119.6(3) . . ?
C2 C1 C6 119.8(4) . . ?
C2 C1 H1A 120.1 . . ?
C6 C1 H1A 120.1 . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 C11 120.5(3) . . ?
C6 C5 C11 120.9(3) . . ?
C1 C6 C5 120.6(4) . . ?
C1 C6 C7 118.3(3) . . ?
C5 C6 C7 121.0(3) . . ?
O1 C7 C6 124.7(3) . . ?
O1 C7 C8 122.3(4) . . ?
C6 C7 C8 112.7(3) . . ?
C9 C8 C22 125.7(3) . . ?
C9 C8 C7 121.3(3) . . ?
C22 C8 C7 112.8(3) . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 C12 122.7(3) . . ?
C10 C9 C12 116.5(3) . . ?
C21 C10 C11 117.4(3) . . ?
C21 C10 C9 119.2(3) . . ?
C11 C10 C9 123.4(3) . . ?
C18 C11 C10 119.6(3) . . ?
C18 C11 C5 116.7(3) . . ?
C10 C11 C5 123.6(3) . . ?
C17 C12 C13 119.1(3) . . ?
C17 C12 C9 118.6(3) . . ?
C13 C12 C9 122.3(3) . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13A 120.1 . . ?
C14 C13 H13A 120.1 . . ?
C15 C14 C13 119.8(4) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C14 C15 C16 120.8(4) . . ?
C14 C15 H15A 119.6 . . ?
C16 C15 H15A 119.6 . . ?
C15 C16 C17 119.9(5) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C12 C17 C16 120.6(4) . . ?
C12 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C19 C18 C11 120.9(3) . . ?
C19 C18 H18A 119.6 . . ?
C11 C18 H18A 119.6 . . ?
O2 C19 C18 115.5(3) . . ?
O2 C19 C20 124.0(3) . . ?
C18 C19 C20 120.5(3) . . ?
C21 C20 C19 119.0(3) . . ?
C21 C20 H20A 120.5 . . ?
C19 C20 H20A 120.5 . . ?
O3 C21 C20 122.9(3) . . ?
O3 C21 C10 114.5(3) . . ?
C20 C21 C10 122.6(3) . . ?
F1 C22 F2 105.9(4) . . ?
F1 C22 F3 105.1(4) . . ?
F2 C22 F3 102.8(4) . . ?
F1 C22 C8 115.0(4) . . ?
F2 C22 C8 112.0(3) . . ?
F3 C22 C8 114.9(3) . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
F1 C22 1.275(5) . ?
F2 C22 1.315(4) . ?
F3 C22 1.327(5) . ?
O1 C7 1.208(4) . ?
O2 C19 1.364(4) . ?
O2 C24 1.426(5) . ?
O3 C21 1.364(4) . ?
O3 C23 1.427(4) . ?
C1 C2 1.381(6) . ?
C1 C6 1.393(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.376(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.372(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.400(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.401(5) . ?
C5 C11 1.489(4) . ?
C6 C7 1.488(5) . ?
C7 C8 1.507(5) . ?
C8 C9 1.337(4) . ?
C8 C22 1.487(5) . ?
C9 C10 1.485(4) . ?
C9 C12 1.504(4) . ?
C10 C21 1.401(4) . ?
C10 C11 1.417(4) . ?
C11 C18 1.396(5) . ?
C12 C17 1.370(5) . ?
C12 C13 1.382(5) . ?
C13 C14 1.403(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.355(7) . ?
C14 H14A 0.9300 . ?
C15 C16 1.358(7) . ?
C15 H15A 0.9300 . ?
C16 C17 1.388(6) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.378(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.385(5) . ?
C20 C21 1.378(5) . ?
C20 H20A 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
