#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/51/4025120.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_4025120
loop_
_publ_author_name
'Carol A. Mulrooney'
'Barbara J. Morgan'
'Xiaolin Li'
'Marisa C. Kozlowski'
_publ_section_title
;
 Perylenequinone Natural Products: Enantioselective Synthesis of the
 Oxidized Pentacyclic Core
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              16
_journal_page_last               29
_journal_paper_doi               10.1021/jo9013832
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C42 H32 Cl6 O14'
_chemical_formula_weight         973.38
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                76.681(2)
_cell_angle_beta                 104.981(7)
_cell_angle_gamma                114.121(7)
_cell_formula_units_Z            2
_cell_length_a                   12.104(4)
_cell_length_b                   12.965(3)
_cell_length_c                   15.309(4)
_cell_measurement_temperature    143(1)
_cell_volume                     2096.8(10)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Altomare, 1993)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi oscillations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12995
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.142
_refine_ls_goodness_of_fit_obs   1.226
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         7307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.144
_refine_ls_restrained_S_obs      1.226
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_obs          0.0678
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0216P)²+3.5407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1171
_refine_ls_wR_factor_obs         0.1079
_reflns_number_observed          5526
_reflns_number_total             7308
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jo9013832_si_003.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0216P)^2^+3.5407P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0216P)^2^+3.5407P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2096.9(10)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4025120
loop_
_symmetry_equiv_pos_as_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
C1 C 0.6907(3) -0.0528(3) 0.8553(2) 0.0154(7) Uani 1 d . .
C2 C 0.6853(3) 0.0553(3) 0.8269(2) 0.0149(7) Uani 1 d . .
C3 C 0.6650(3) 0.1063(3) 0.8900(2) 0.0149(7) Uani 1 d . .
C4 C 0.6510(3) 0.0496(3) 0.9790(2) 0.0142(7) Uani 1 d . .
C5 C 0.6421(3) 0.1078(3) 1.0451(2) 0.0148(7) Uani 1 d . .
C6 C 0.6288(3) 0.0453(3) 1.1416(2) 0.0171(8) Uani 1 d . .
C7 C 0.6328(3) -0.0698(3) 1.1634(2) 0.0162(7) Uani 1 d . .
C8 C 0.6420(3) -0.1199(3) 1.0993(2) 0.0148(7) Uani 1 d . .
H8 H 0.6396(3) -0.1944(3) 1.1145(2) 0.020 Uiso 1 calc R .
C9 C 0.6558(3) -0.0617(3) 1.0069(2) 0.0139(7) Uani 1 d . .
C10 C 0.6751(3) -0.1128(3) 0.9445(2) 0.0137(7) Uani 1 d . .
C11 C 0.6911(3) -0.2259(3) 0.9679(2) 0.0132(7) Uani 1 d . .
C12 C 0.8060(3) -0.2271(3) 1.0221(2) 0.0154(7) Uani 1 d . .
C13 C 0.8370(3) -0.3235(3) 1.0401(2) 0.0169(8) Uani 1 d . .
C14 C 0.7504(3) -0.4203(3) 1.0008(2) 0.0170(8) Uani 1 d . .
C15 C 0.6367(3) -0.4221(3) 0.9487(2) 0.0147(7) Uani 1 d . .
C16 C 0.5547(3) -0.5201(3) 0.9046(2) 0.0179(8) Uani 1 d . .
C17 C 0.4308(3) -0.5191(3) 0.8467(2) 0.0187(8) Uani 1 d . .
C18 C 0.4063(3) -0.4146(3) 0.8351(2) 0.0169(8) Uani 1 d . .
C19 C 0.4873(3) -0.3238(3) 0.8757(2) 0.0152(7) Uani 1 d . .
H19 H 0.4675(3) -0.2597(3) 0.8679(2) 0.020 Uiso 1 calc R .
C20 C 0.6055(3) -0.3229(3) 0.9315(2) 0.0143(7) Uani 1 d . .
C22 C 0.6647(4) -0.1089(3) 0.7077(2) 0.0279(9) Uani 1 d . .
H22A H 0.7234(4) -0.0514(3) 0.6720(2) 0.037 Uiso 1 calc R .
H22B H 0.5903(4) -0.0923(3) 0.6934(2) 0.037 Uiso 1 calc R .
C23 C 0.6360(3) -0.2265(3) 0.6863(2) 0.0221(8) Uani 1 d . .
C24 C 0.5300(4) -0.2782(3) 0.6258(3) 0.0350(10) Uani 1 d . .
H24 H 0.4749(4) -0.2416(3) 0.5997(3) 0.047 Uiso 1 calc R .
C25 C 0.5059(4) -0.3841(4) 0.6041(3) 0.0440(12) Uani 1 d . .
H25 H 0.4353(4) -0.4179(4) 0.5627(3) 0.058 Uiso 1 calc R .
C26 C 0.5858(5) -0.4393(4) 0.6433(3) 0.0504(13) Uani 1 d . .
H26 H 0.5693(5) -0.5105(4) 0.6287(3) 0.067 Uiso 1 calc R .
C27 C 0.6901(5) -0.3894(4) 0.7041(4) 0.0519(13) Uani 1 d . .
H27 H 0.7436(5) -0.4276(4) 0.7313(4) 0.069 Uiso 1 calc R .
C28 C 0.7164(4) -0.2826(3) 0.7252(3) 0.0348(10) Uani 1 d . .
H28 H 0.7881(4) -0.2486(3) 0.7656(3) 0.046 Uiso 1 calc R .
C29 C 0.7187(3) 0.1261(3) 0.7383(2) 0.0184(8) Uani 1 d . .
C32 C 0.6626(4) 0.2441(4) 0.6081(3) 0.0407(11) Uani 1 d . .
H32A H 0.7269(18) 0.3143(10) 0.6244(3) 0.061 Uiso 1 calc R .
H32B H 0.5910(8) 0.2590(19) 0.5735(10) 0.061 Uiso 1 calc R .
H32C H 0.6901(25) 0.2111(11) 0.5720(10) 0.061 Uiso 1 calc R .
C37 C 0.6106(4) -0.2300(3) 1.2790(3) 0.0301(10) Uani 1 d . .
H37A H 0.5984(24) -0.2529(7) 1.3412(6) 0.045 Uiso 1 calc R .
H37B H 0.6842(10) -0.2379(5) 1.2743(17) 0.045 Uiso 1 calc R .
H37C H 0.5413(14) -0.2775(4) 1.2404(11) 0.045 Uiso 1 calc R .
C39 C 0.9660(3) -0.1154(3) 1.1367(2) 0.0224(8) Uani 1 d . .
H39A H 1.0482(3) -0.0980(3) 1.1270(2) 0.030 Uiso 1 calc R .
H39B H 0.9421(3) -0.1864(3) 1.1781(2) 0.030 Uiso 1 calc R .
C40 C 0.9635(3) -0.0205(3) 1.1760(2) 0.0195(8) Uani 1 d . .
C41 C 0.9759(4) -0.0277(3) 1.2697(3) 0.0274(9) Uani 1 d . .
H41 H 0.9864(4) -0.0912(3) 1.3081(3) 0.036 Uiso 1 calc R .
C42 C 0.9728(4) 0.0591(4) 1.3064(3) 0.0339(10) Uani 1 d . .
H42 H 0.9820(4) 0.0539(4) 1.3692(3) 0.045 Uiso 1 calc R .
C43 C 0.9562(4) 0.1532(3) 1.2497(3) 0.0341(10) Uani 1 d . .
H43 H 0.9522(4) 0.2105(3) 1.2743(3) 0.045 Uiso 1 calc R .
C44 C 0.9456(3) 0.1626(3) 1.1562(3) 0.0281(9) Uani 1 d . .
H44 H 0.9356(3) 0.2265(3) 1.1180(3) 0.037 Uiso 1 calc R .
C45 C 0.9502(3) 0.0761(3) 1.1202(3) 0.0226(8) Uani 1 d . .
H45 H 0.9443(3) 0.0828(3) 1.0575(3) 0.030 Uiso 1 calc R .
C46 C 0.9618(3) -0.3244(3) 1.0856(3) 0.0210(8) Uani 1 d . .
C49 C 1.0697(4) -0.4284(4) 1.1926(3) 0.0438(12) Uani 1 d . .
H49A H 1.0563(7) -0.4909(16) 1.2416(13) 0.066 Uiso 1 calc R .
H49B H 1.1309(9) -0.3606(9) 1.2156(18) 0.066 Uiso 1 calc R .
H49C H 1.0977(14) -0.4459(24) 1.1465(6) 0.066 Uiso 1 calc R .
C54 C 0.2530(4) -0.3349(3) 0.7700(3) 0.0304(9) Uani 1 d . .
H54A H 0.1700(9) -0.3565(9) 0.7364(15) 0.046 Uiso 1 calc R .
H54B H 0.3052(15) -0.2681(7) 0.7369(15) 0.046 Uiso 1 calc R .
H54C H 0.2555(22) -0.3187(15) 0.8287(3) 0.046 Uiso 1 calc R .
O21 O 0.7156(2) -0.1091(2) 0.8034(2) 0.0197(5) Uani 1 d . .
O30 O 0.6320(2) 0.1653(2) 0.6905(2) 0.0306(7) Uani 1 d . .
O31 O 0.8135(2) 0.1462(2) 0.7150(2) 0.0296(6) Uani 1 d . .
O33 O 0.6634(2) 0.2117(2) 0.8636(2) 0.0194(5) Uani 1 d . .
H33 H 0.6501(37) 0.2324(14) 0.9053(10) 0.029 Uiso 1 calc R .
O34 O 0.6451(2) 0.2070(2) 1.0279(2) 0.0225(6) Uani 1 d . .
O35 O 0.6136(2) 0.0911(2) 1.1963(2) 0.0267(6) Uani 1 d . .
O36 O 0.6221(2) -0.1134(2) 1.2511(2) 0.0219(6) Uani 1 d . .
O38 O 0.8800(2) -0.1258(2) 1.0507(2) 0.0188(5) Uani 1 d . .
O47 O 0.9558(2) -0.4102(2) 1.1534(2) 0.0311(7) Uani 1 d . .
O48 O 1.0558(2) -0.2575(2) 1.0623(2) 0.0304(6) Uani 1 d . .
O50 O 0.7836(2) -0.5105(2) 1.0123(2) 0.0258(6) Uani 1 d . .
H50 H 0.7278(16) -0.5613(14) 0.9857(24) 0.039 Uiso 1 calc R .
O51 O 0.5775(2) -0.6067(2) 0.9104(2) 0.0255(6) Uani 1 d . .
O52 O 0.3578(2) -0.6037(2) 0.8134(2) 0.0278(6) Uani 1 d . .
O53 O 0.2953(2) -0.4265(2) 0.7817(2) 0.0232(6) Uani 1 d . .
C55 C 0.2547(4) -0.0292(3) 0.5742(3) 0.0331(10) Uani 1 d . .
H55 H 0.2590(4) -0.0345(3) 0.6399(3) 0.044 Uiso 1 calc R .
Cl1 Cl 0.22493(12) 0.09334(10) 0.51746(8) 0.0519(3) Uani 1 d . .
Cl2 Cl 0.39625(12) -0.01955(13) 0.55604(10) 0.0616(4) Uani 1 d . .
Cl3 Cl 0.13621(12) -0.15170(10) 0.53455(9) 0.0520(3) Uani 1 d . .
C56 C -0.1727(4) -0.4309(3) 0.3931(3) 0.0316(10) Uani 1 d . .
H56 H -0.2385(4) -0.4410(3) 0.3390(3) 0.042 Uiso 1 calc R .
Cl4 Cl -0.03340(11) -0.33587(9) 0.35961(8) 0.0457(3) Uani 1 d . .
Cl5 Cl -0.20895(13) -0.37558(11) 0.47185(9) 0.0579(4) Uani 1 d . .
Cl6 Cl -0.16324(11) -0.56499(9) 0.44189(8) 0.0433(3) Uani 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 0.0033 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'
O O 0.0106 0.0060 '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'
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
O21 C1 C2 124.0(3) . . ?
O21 C1 C10 113.5(3) . . ?
C2 C1 C10 122.5(3) . . ?
C1 C2 C3 117.8(3) . . ?
C1 C2 C29 123.0(3) . . ?
C3 C2 C29 118.5(3) . . ?
O33 C3 C4 121.2(3) . . ?
O33 C3 C2 117.9(3) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C9 120.7(3) . . ?
C3 C4 C5 119.8(3) . . ?
C9 C4 C5 119.3(3) . . ?
O34 C5 C4 123.4(3) . . ?
O34 C5 C6 117.6(3) . . ?
C4 C5 C6 119.0(3) . . ?
O35 C6 C7 123.0(3) . . ?
O35 C6 C5 119.5(3) . . ?
C7 C6 C5 117.5(3) . . ?
C8 C7 O36 128.1(3) . . ?
C8 C7 C6 121.0(3) . . ?
O36 C7 C6 110.9(3) . . ?
C7 C8 C9 122.5(3) . . ?
C10 C9 C4 118.7(3) . . ?
C10 C9 C8 120.8(3) . . ?
C4 C9 C8 120.5(3) . . ?
C9 C10 C1 119.4(3) . . ?
C9 C10 C11 123.6(3) . . ?
C1 C10 C11 116.8(3) . . ?
C20 C11 C12 120.1(3) . . ?
C20 C11 C10 122.7(3) . . ?
C12 C11 C10 116.9(3) . . ?
O38 C12 C13 124.9(3) . . ?
O38 C12 C11 112.9(3) . . ?
C13 C12 C11 122.2(3) . . ?
C12 C13 C14 117.1(3) . . ?
C12 C13 C46 124.0(3) . . ?
C14 C13 C46 118.2(3) . . ?
O50 C14 C15 120.8(3) . . ?
O50 C14 C13 117.2(3) . . ?
C15 C14 C13 121.9(3) . . ?
C14 C15 C20 120.5(3) . . ?
C14 C15 C16 119.9(3) . . ?
C20 C15 C16 119.4(3) . . ?
O51 C16 C15 124.0(3) . . ?
O51 C16 C17 117.2(3) . . ?
C15 C16 C17 118.8(3) . . ?
O52 C17 C18 123.1(3) . . ?
O52 C17 C16 119.5(3) . . ?
C18 C17 C16 117.5(3) . . ?
C19 C18 O53 128.1(3) . . ?
C19 C18 C17 121.5(3) . . ?
O53 C18 C17 110.3(3) . . ?
C18 C19 C20 122.0(3) . . ?
C11 C20 C15 118.3(3) . . ?
C11 C20 C19 121.2(3) . . ?
C15 C20 C19 120.6(3) . . ?
O21 C22 C23 107.1(3) . . ?
C28 C23 C24 119.2(4) . . ?
C28 C23 C22 120.4(4) . . ?
C24 C23 C22 120.4(3) . . ?
C25 C24 C23 120.3(4) . . ?
C26 C25 C24 120.1(4) . . ?
C25 C26 C27 120.0(4) . . ?
C26 C27 C28 120.5(5) . . ?
C23 C28 C27 119.9(4) . . ?
O31 C29 O30 124.5(3) . . ?
O31 C29 C2 123.7(3) . . ?
O30 C29 C2 111.8(3) . . ?
O38 C39 C40 107.3(3) . . ?
C45 C40 C41 118.7(3) . . ?
C45 C40 C39 121.1(3) . . ?
C41 C40 C39 120.2(3) . . ?
C42 C41 C40 120.5(4) . . ?
C43 C42 C41 120.1(4) . . ?
C42 C43 C44 120.2(4) . . ?
C43 C44 C45 119.3(4) . . ?
C44 C45 C40 121.2(4) . . ?
O48 C46 O47 124.0(3) . . ?
O48 C46 C13 124.1(3) . . ?
O47 C46 C13 111.8(3) . . ?
C1 O21 C22 122.0(3) . . ?
C29 O30 C32 115.3(3) . . ?
C7 O36 C37 116.9(3) . . ?
C12 O38 C39 123.2(2) . . ?
C46 O47 C49 115.8(3) . . ?
C18 O53 C54 117.2(3) . . ?
Cl1 C55 Cl3 110.2(2) . . ?
Cl1 C55 Cl2 109.7(2) . . ?
Cl3 C55 Cl2 109.9(2) . . ?
Cl4 C56 Cl5 110.3(2) . . ?
Cl4 C56 Cl6 110.5(2) . . ?
Cl5 C56 Cl6 109.8(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 O21 1.351(4) . ?
C1 C2 1.392(4) . ?
C1 C10 1.424(5) . ?
C2 C3 1.408(5) . ?
C2 C29 1.500(5) . ?
C3 O33 1.339(4) . ?
C3 C4 1.407(5) . ?
C4 C9 1.428(4) . ?
C4 C5 1.442(4) . ?
C5 O34 1.239(4) . ?
C5 C6 1.526(5) . ?
C6 O35 1.218(4) . ?
C6 C7 1.471(5) . ?
C7 C8 1.343(5) . ?
C7 O36 1.349(4) . ?
C8 C9 1.458(5) . ?
C9 C10 1.394(5) . ?
C10 C11 1.506(4) . ?
C11 C20 1.388(5) . ?
C11 C12 1.427(5) . ?
C12 O38 1.349(4) . ?
C12 C13 1.397(5) . ?
C13 C14 1.407(5) . ?
C13 C46 1.495(5) . ?
C14 O50 1.346(4) . ?
C14 C15 1.396(5) . ?
C15 C20 1.434(4) . ?
C15 C16 1.439(5) . ?
C16 O51 1.241(4) . ?
C16 C17 1.536(5) . ?
C17 O52 1.215(4) . ?
C17 C18 1.465(5) . ?
C18 C19 1.345(5) . ?
C18 O53 1.349(4) . ?
C19 C20 1.461(5) . ?
C22 O21 1.434(4) . ?
C22 C23 1.514(5) . ?
C23 C28 1.382(5) . ?
C23 C24 1.386(5) . ?
C24 C25 1.383(6) . ?
C25 C26 1.369(7) . ?
C26 C27 1.372(7) . ?
C27 C28 1.384(6) . ?
C29 O31 1.199(4) . ?
C29 O30 1.328(4) . ?
C32 O30 1.453(4) . ?
C37 O36 1.431(4) . ?
C39 O38 1.446(4) . ?
C39 C40 1.503(5) . ?
C40 C45 1.387(5) . ?
C40 C41 1.388(5) . ?
C41 C42 1.385(5) . ?
C42 C43 1.380(6) . ?
C43 C44 1.384(6) . ?
C44 C45 1.385(5) . ?
C46 O48 1.197(4) . ?
C46 O47 1.328(4) . ?
C49 O47 1.446(4) . ?
C54 O53 1.434(4) . ?
C55 Cl1 1.754(4) . ?
C55 Cl3 1.755(4) . ?
C55 Cl2 1.757(4) . ?
C56 Cl4 1.756(4) . ?
C56 Cl5 1.758(4) . ?
C56 Cl6 1.764(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659106
2 PubChem 139091365
