#------------------------------------------------------------------------------
#$Date: 2021-05-05 12:05:26 +0300 (Wed, 05 May 2021) $
#$Revision: 264963 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157978.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_7157978
loop_
_publ_author_name
'Nechaev, Anton A.'
'Jagtap, Pratap R.'
'BaŽíková, Ema'
'Neumannová, Johana'
'Císařová, Ivana'
'Matoušová, Eliška'
_publ_section_title
;
 Synthesis of fused 1,2-naphthoquinones with cytotoxic activity using a
 one-pot three-step reaction.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3434
_journal_page_last               3440
_journal_paper_doi               10.1039/d1ob00205h
_journal_volume                  19
_journal_year                    2021
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C17 H15 Cl3 O3'
_chemical_formula_sum            'C17 H15 Cl3 O3'
_chemical_formula_weight         373.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-02-20 deposited with the CCDC.	2021-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.5473(6)
_cell_length_b                   6.9275(2)
_cell_length_c                   10.8993(3)
_cell_measurement_reflns_used    9616
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.1208
_cell_measurement_theta_min      4.5463
_cell_volume                     1626.93(8)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.12'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26286
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.267
_diffrn_reflns_theta_min         4.546
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    5.205
_exptl_absorpt_correction_T_max  0.51
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_description       bar
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.151
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0458P)²+1.4029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1259
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1696
_reflns_number_total             1738
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00205h2.cif
_cod_data_source_block           cu_aa_114bs_matousova
_cod_depositor_comments          'Adding full bibliography for 7157978.cif.'
_cod_database_code               7157978
_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_min   0.237
_shelx_estimated_absorpt_t_max   0.507
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
C1 C 0.61918(14) 0.250000 0.7125(3) 0.0428(7) Uani 1 2 d S T P . .
H1A H 0.639799 0.365290 0.677540 0.051 Uiso 0.5 1 d R U P . .
H1B H 0.639799 0.134710 0.677540 0.051 Uiso 0.5 1 d R U P . .
O1 O 0.46278(12) 0.2094(6) 0.9501(2) 0.0425(15) Uani 0.5 1 d . . P . .
C2 C 0.62830(19) 0.2840(14) 0.8514(3) 0.044(3) Uani 0.5 1 d . . P . .
H2A H 0.669482 0.233709 0.875948 0.053 Uiso 0.5 1 d R U P . .
H2B H 0.627571 0.424362 0.868274 0.053 Uiso 0.5 1 d R U P . .
O2 O 0.58445(15) 0.250000 0.2308(2) 0.0685(8) Uani 1 2 d S T P . .
C3 C 0.57811(19) 0.1846(7) 0.9288(3) 0.0431(11) Uani 0.5 1 d . . P . .
H3A H 0.571189 0.064899 0.917442 0.052 Uiso 0.5 1 d R U P . .
H3B H 0.591591 0.214500 1.015334 0.052 Uiso 0.5 1 d R U P . .
O3 O 0.62971(11) 0.250000 0.4579(2) 0.0552(7) Uani 1 2 d S T P . .
C4 C 0.51874(18) 0.2894(6) 0.8976(3) 0.0360(16) Uani 0.5 1 d . . P . .
H4 H 0.522310 0.430876 0.914505 0.043 Uiso 0.5 1 d R U P . .
C5 C 0.41313(15) 0.250000 0.8648(3) 0.0448(8) Uani 1 2 d S T P . .
H5A H 0.386851 0.366214 0.874637 0.054 Uiso 0.5 1 d R U P . .
H5B H 0.386851 0.133786 0.874637 0.054 Uiso 0.5 1 d R U P . .
C6 C 0.44441(13) 0.250000 0.7410(3) 0.0328(6) Uani 1 2 d S T P . .
C7 C 0.42124(14) 0.250000 0.6222(3) 0.0349(6) Uani 1 2 d S T P . .
C8 C 0.46481(14) 0.250000 0.5260(2) 0.0317(6) Uani 1 2 d S T P . .
C9 C 0.44348(16) 0.250000 0.3987(3) 0.0413(7) Uani 1 2 d S T P . .
H9 H 0.399976 0.250000 0.384553 0.050 Uiso 1 2 calc R U P . .
C10 C 0.48107(18) 0.250000 0.2999(3) 0.0469(8) Uani 1 2 d S T P . .
H10 H 0.463642 0.250000 0.219864 0.056 Uiso 1 2 calc R U P . .
C11 C 0.54741(18) 0.250000 0.3148(3) 0.0441(8) Uani 1 2 d S T P . .
C12 C 0.57368(15) 0.250000 0.4467(3) 0.0378(7) Uani 1 2 d S T P . .
C13 C 0.52993(13) 0.250000 0.5506(2) 0.0311(6) Uani 1 2 d S T P . .
C14 C 0.55186(14) 0.250000 0.6721(2) 0.0349(6) Uani 1 2 d S T P . .
C15 C 0.50703(14) 0.250000 0.7629(3) 0.0421(7) Uani 1 2 d S T P . .
C16 C 0.35197(15) 0.250000 0.6014(3) 0.0522(9) Uani 1 2 d S T P . .
H16A H 0.330647 0.225421 0.679244 0.078 Uiso 0.5 1 calc R U P . .
H16B H 0.341182 0.148762 0.542309 0.078 Uiso 0.5 1 calc R U P . .
H16C H 0.339124 0.375817 0.569060 0.078 Uiso 0.5 1 calc R U P . .
C1S C 0.73121(17) 0.250000 0.2351(4) 0.0571(10) Uani 1 2 d S T P . .
H1S H 0.689781 0.250000 0.276488 0.068 Uiso 1 2 d R U P . .
Cl1S Cl 0.79010(8) 0.250000 0.34738(12) 0.1024(5) Uani 1 2 d S T P . .
Cl2S Cl 0.73746(3) 0.45682(12) 0.14263(7) 0.0664(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C14 C1 C2 114.0(3) . 7_565 ?
C14 C1 C2 114.0(3) . . ?
C2 C1 C2 17.5(7) 7_565 . ?
C14 C1 H1A 108.5 . . ?
C2 C1 H1A 116.3 7_565 . ?
C2 C1 H1A 101.4 . . ?
C14 C1 H1B 108.5 . . ?
C2 C1 H1B 101.4 7_565 . ?
C2 C1 H1B 116.3 . . ?
H1A C1 H1B 107.5 . . ?
O1 O1 C4 89.7(3) 7_565 7_565 ?
O1 O1 C4 67.5(2) 7_565 . ?
C4 O1 C4 22.2(4) 7_565 . ?
O1 O1 C5 78.79(17) 7_565 . ?
C4 O1 C5 113.1(3) 7_565 . ?
C4 O1 C5 106.8(3) . . ?
C2 C2 C3 99.0(4) 7_565 7_565 ?
C2 C2 C3 63.4(4) 7_565 . ?
C3 C2 C3 35.6(4) 7_565 . ?
C2 C2 C1 81.2(4) 7_565 . ?
C3 C2 C1 121.4(3) 7_565 . ?
C3 C2 C1 112.4(4) . . ?
C2 C2 H2A 69.4 7_565 . ?
C3 C2 H2A 126.0 7_565 . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C2 C2 H2B 169.2 7_565 . ?
C3 C2 H2B 73.8 7_565 . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C2 C2 H2A 82.5(12) 7_565 7_565 ?
C3 C2 H2A 125.8(2) 7_565 7_565 ?
C3 C2 H2A 116.9(8) . 7_565 ?
C1 C2 H2A 112.4(4) . 7_565 ?
H2A C2 H2A 13.1 . 7_565 ?
H2B C2 H2A 95.2 . 7_565 ?
C3 C3 C4 82.3(3) 7_565 7_565 ?
C3 C3 C2 81.0(4) 7_565 7_565 ?
C4 C3 C2 124.8(4) 7_565 7_565 ?
C3 C3 C4 61.3(2) 7_565 . ?
C4 C3 C4 21.0(3) 7_565 . ?
C2 C3 C4 116.6(4) 7_565 . ?
C3 C3 C2 63.4(4) 7_565 . ?
C4 C3 C2 118.3(4) 7_565 . ?
C2 C3 C2 17.6(7) 7_565 . ?
C4 C3 C2 104.9(4) . . ?
C3 C3 H3A 166.9 7_565 . ?
C4 C3 H3A 85.8 7_565 . ?
C2 C3 H3A 101.6 7_565 . ?
C4 C3 H3A 106.7 . . ?
C2 C3 H3A 118.7 . . ?
C3 C3 H3B 78.2 7_565 . ?
C4 C3 H3B 119.1 7_565 . ?
C2 C3 H3B 108.2 7_565 . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 102.7 . . ?
H3A C3 H3B 112.7 . . ?
C4 C4 O1 90.3(3) 7_565 7_565 ?
C4 C4 C3 97.7(3) 7_565 7_565 ?
O1 C4 C3 139.1(3) 7_565 7_565 ?
C4 C4 O1 67.4(2) 7_565 . ?
O1 C4 O1 22.9(4) 7_565 . ?
C3 C4 O1 138.6(3) 7_565 . ?
C4 C4 C3 61.3(2) 7_565 . ?
O1 C4 C3 132.2(4) 7_565 . ?
C3 C4 C3 36.5(4) 7_565 . ?
O1 C4 C3 115.7(4) . . ?
C4 C4 C15 79.61(17) 7_565 . ?
O1 C4 C15 105.4(3) 7_565 . ?
C3 C4 C15 115.5(3) 7_565 . ?
O1 C4 C15 100.1(3) . . ?
C3 C4 C15 105.8(3) . . ?
C4 C4 H4 168.5 7_565 . ?
O1 C4 H4 89.1 7_565 . ?
C3 C4 H4 75.4 7_565 . ?
O1 C4 H4 111.5 . . ?
C3 C4 H4 111.4 . . ?
C15 C4 H4 111.6 . . ?
O1 C5 O1 22.4(3) . 7_565 ?
O1 C5 C6 104.2(2) . . ?
O1 C5 C6 104.2(2) 7_565 . ?
O1 C5 H5A 120.8 . . ?
O1 C5 H5A 101.3 7_565 . ?
C6 C5 H5A 110.7 . . ?
O1 C5 H5B 101.3 . . ?
O1 C5 H5B 120.8 7_565 . ?
C6 C5 H5B 110.7 . . ?
H5A C5 H5B 108.8 . . ?
C15 C6 C7 121.1(3) . . ?
C15 C6 C5 106.5(2) . . ?
C7 C6 C5 132.4(3) . . ?
C6 C7 C8 117.1(3) . . ?
C6 C7 C16 119.7(3) . . ?
C8 C7 C16 123.2(3) . . ?
C7 C8 C13 121.0(2) . . ?
C7 C8 C9 119.8(3) . . ?
C13 C8 C9 119.1(3) . . ?
C10 C9 C8 124.7(3) . . ?
C10 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
O2 C11 C10 124.6(3) . . ?
O2 C11 C12 117.5(3) . . ?
C10 C11 C12 118.0(3) . . ?
O3 C12 C13 124.0(3) . . ?
O3 C12 C11 117.3(3) . . ?
C13 C12 C11 118.7(3) . . ?
C14 C13 C8 120.5(2) . . ?
C14 C13 C12 120.6(3) . . ?
C8 C13 C12 119.0(2) . . ?
C15 C14 C13 116.1(3) . . ?
C15 C14 C1 117.4(3) . . ?
C13 C14 C1 126.5(3) . . ?
C6 C15 C14 124.3(3) . . ?
C6 C15 C4 109.4(3) . . ?
C14 C15 C4 125.3(3) . . ?
C6 C15 C4 109.4(3) . 7_565 ?
C14 C15 C4 125.3(3) . 7_565 ?
C4 C15 C4 20.8(3) . 7_565 ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C16 H16A 109.5(4) . 7_565 ?
H16A C16 H16A 20.0 . 7_565 ?
H16B C16 H16A 125.6 . 7_565 ?
H16C C16 H16A 91.4 . 7_565 ?
C7 C16 H16B 109.5(10) . 7_565 ?
H16A C16 H16B 125.6 . 7_565 ?
H16B C16 H16B 91.4 . 7_565 ?
H16C C16 H16B 20.0 . 7_565 ?
H16A C16 H16B 109.5 7_565 7_565 ?
C7 C16 H16C 109.5(6) . 7_565 ?
H16A C16 H16C 91.4 . 7_565 ?
H16B C16 H16C 20.0 . 7_565 ?
H16C C16 H16C 125.6 . 7_565 ?
H16A C16 H16C 109.5 7_565 7_565 ?
H16B C16 H16C 109.5 7_565 7_565 ?
Cl2S C1S Cl2S 109.3(2) . 7_565 ?
Cl2S C1S Cl1S 110.06(14) . . ?
Cl2S C1S Cl1S 110.06(14) 7_565 . ?
Cl2S C1S H1S 109.1 . . ?
Cl2S C1S H1S 109.1 7_565 . ?
Cl1S C1S H1S 109.2 . . ?
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
C1 C14 1.516(4) . ?
C1 C2 1.544(5) 7_565 ?
C1 C2 1.544(5) . ?
C1 H1A 0.9901 . ?
C1 H1B 0.9901 . ?
O1 O1 0.562(9) 7_565 ?
O1 C4 1.334(4) 7_565 ?
O1 C4 1.445(5) . ?
O1 C5 1.445(4) . ?
C2 C2 0.471(19) 7_565 ?
C2 C3 1.389(6) 7_565 ?
C2 C3 1.535(7) . ?
C2 H2A 0.9901 . ?
C2 H2B 0.9901 . ?
C2 H2A 0.935(3) 7_565 ?
O2 C11 1.215(4) . ?
C3 C3 0.906(9) 7_565 ?
C3 C4 1.336(6) 7_565 ?
C3 C4 1.510(6) . ?
C3 H3A 0.8518 . ?
C3 H3B 1.0084 . ?
O3 C12 1.214(4) . ?
C4 C4 0.546(9) 7_565 ?
C4 C15 1.515(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.508(4) . ?
C5 H5A 0.9901 . ?
C5 H5B 0.9901 . ?
C6 C15 1.370(4) . ?
C6 C7 1.388(4) . ?
C7 C8 1.407(4) . ?
C7 C16 1.510(4) . ?
C8 C13 1.429(4) . ?
C8 C9 1.462(4) . ?
C9 C10 1.347(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.439(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.545(4) . ?
C12 C13 1.473(4) . ?
C13 C14 1.406(4) . ?
C14 C15 1.383(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16A 0.980(18) 7_565 ?
C16 H16B 0.98(5) 7_565 ?
C16 H16C 0.98(3) 7_565 ?
C1S Cl2S 1.757(2) . ?
C1S Cl2S 1.757(2) 7_565 ?
C1S Cl1S 1.763(4) . ?
C1S H1S 1.0001 . ?
