#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/57/7155782.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_7155782
loop_
_publ_author_name
'Saunthwal, Rakesh K.'
'Danodia, abhinandan K.'
'Saini, Kapil Mohan'
'Verma, Akhilesh K.'
_publ_section_title
;
 Ag(I)-Catalyzed Cycloisomerization Reactions: Synthesis of Substituted
 Phenanthrenes and Naphthothiophenes
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01646H
_journal_year                    2017
_chemical_formula_moiety         'C25 H24 O'
_chemical_formula_sum            'C25 H24 O'
_chemical_formula_weight         340.44
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-05-28 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.703(2)
_cell_length_b                   8.2643(5)
_cell_length_c                   23.1696(19)
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.30
_cell_volume                     3772.7(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13457
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_correction_T_min  0.9838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0969
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0884P)²+5.5316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2312
_refine_ls_wR_factor_ref         0.2465
_reflns_number_gt                2564
_reflns_number_total             3315
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob01646h2.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        3772.7(6)
_cod_database_code               7155782
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C24 C 0.2575(2) 0.1493(5) 0.3476(2) 0.0700(13) Uani 1 1 d .
H24A H 0.3054 0.1762 0.3416 0.105 Uiso 1 1 calc R
H24B H 0.2496 0.0359 0.3372 0.105 Uiso 1 1 calc R
H24C H 0.2457 0.1659 0.3883 0.105 Uiso 1 1 calc R
O1 O 0.21627(15) 0.2510(4) 0.31246(13) 0.0648(9) Uani 1 1 d .
C1 C 0.1140(3) -0.6936(5) 0.49241(19) 0.0726(15) Uani 1 1 d .
H1A H 0.1218 -0.7121 0.4512 0.109 Uiso 1 1 calc R
H1B H 0.0654 -0.7010 0.5007 0.109 Uiso 1 1 calc R
H1C H 0.1385 -0.7756 0.5148 0.109 Uiso 1 1 calc R
C2 C 0.1260(4) -0.5055(6) 0.5725(2) 0.118(3) Uani 1 1 d .
H2A H 0.1423 -0.3986 0.5844 0.178 Uiso 1 1 calc R
H2B H 0.1499 -0.5893 0.5945 0.178 Uiso 1 1 calc R
H2C H 0.0772 -0.5135 0.5800 0.178 Uiso 1 1 calc R
C3 C 0.2152(3) -0.5267(8) 0.4977(4) 0.140(4) Uani 1 1 d .
H3A H 0.2240 -0.5408 0.4564 0.210 Uiso 1 1 calc R
H3B H 0.2368 -0.6148 0.5193 0.210 Uiso 1 1 calc R
H3C H 0.2340 -0.4228 0.5105 0.210 Uiso 1 1 calc R
C4 C 0.1393(2) -0.5292(4) 0.50851(16) 0.0465(10) Uani 1 1 d .
C5 C 0.10581(19) -0.3954(4) 0.47282(15) 0.0408(9) Uani 1 1 d .
C6 C 0.1005(3) -0.2418(5) 0.4922(2) 0.0797(17) Uani 1 1 d .
H6 H 0.1178 -0.2167 0.5294 0.096 Uiso 1 1 calc R
C7 C 0.0708(3) -0.1196(5) 0.4601(2) 0.0853(19) Uani 1 1 d .
H7 H 0.0694 -0.0133 0.4757 0.102 Uiso 1 1 calc R
C8 C 0.04381(18) -0.1469(4) 0.40726(15) 0.0391(9) Uani 1 1 d .
C9 C 0.0483(3) -0.3016(5) 0.38685(17) 0.0687(14) Uani 1 1 d .
H9 H 0.0302 -0.3261 0.3499 0.082 Uiso 1 1 calc R
C10 C 0.0786(3) -0.4232(5) 0.41849(18) 0.0722(15) Uani 1 1 d .
H10 H 0.0809 -0.5291 0.4026 0.087 Uiso 1 1 calc R
C11 C 0.00694(19) -0.0190(4) 0.37478(14) 0.0386(9) Uani 1 1 d .
C12 C -0.0617(2) -0.0206(5) 0.37338(16) 0.0476(10) Uani 1 1 d .
H12 H -0.0848 -0.1051 0.3931 0.057 Uiso 1 1 calc R
C13 C -0.10110(19) 0.0978(4) 0.34387(15) 0.0415(9) Uani 1 1 d .
C14 C -0.1723(2) 0.0926(5) 0.34474(17) 0.0520(10) Uani 1 1 d .
H14 H -0.1947 0.0091 0.3655 0.062 Uiso 1 1 calc R
C15 C -0.2098(2) 0.2063(5) 0.31608(17) 0.0555(11) Uani 1 1 d .
H15 H -0.2580 0.2019 0.3170 0.067 Uiso 1 1 calc R
C015 C -0.1772(2) 0.3282(5) 0.28563(17) 0.0556(11) Uani 1 1 d .
H015 H -0.2032 0.4074 0.2658 0.067 Uiso 1 1 calc R
C16 C -0.1081(2) 0.3351(5) 0.28399(15) 0.0483(10) Uani 1 1 d .
H16 H -0.0867 0.4195 0.2629 0.058 Uiso 1 1 calc R
C17 C -0.06777(19) 0.2204(4) 0.31271(14) 0.0398(9) Uani 1 1 d .
C18 C 0.00590(19) 0.2237(4) 0.31231(13) 0.0377(9) Uani 1 1 d .
C19 C 0.0431(2) 0.3414(4) 0.28131(14) 0.0445(10) Uani 1 1 d .
H19 H 0.0191 0.4199 0.2593 0.053 Uiso 1 1 calc R
C20 C 0.1115(2) 0.3456(5) 0.28202(17) 0.0510(10) Uani 1 1 d .
H20 H 0.1350 0.4261 0.2606 0.061 Uiso 1 1 calc R
C21 C 0.1477(2) 0.2320(4) 0.31410(16) 0.0451(9) Uani 1 1 d .
C22 C 0.1143(2) 0.1134(4) 0.34366(14) 0.0403(9) Uani 1 1 d .
H22 H 0.1394 0.0342 0.3643 0.048 Uiso 1 1 calc R
C23 C 0.04294(18) 0.1075(4) 0.34372(13) 0.0355(8) 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C21 O1 C24 118.8(3)
C1 C4 C2 107.7(4)
C1 C4 C5 112.3(3)
C2 C4 C5 111.1(4)
C1 C4 C3 107.4(4)
C2 C4 C3 109.2(5)
C5 C4 C3 109.0(3)
C6 C5 C10 115.3(4)
C6 C5 C4 122.2(3)
C10 C5 C4 122.5(3)
C5 C6 C7 122.7(4)
C8 C7 C6 122.0(4)
C7 C8 C9 116.3(4)
C7 C8 C11 122.1(3)
C9 C8 C11 121.5(3)
C8 C9 C10 121.8(4)
C5 C10 C9 121.9(4)
C12 C11 C23 118.9(3)
C12 C11 C8 119.6(3)
C23 C11 C8 121.5(3)
C11 C12 C13 123.3(3)
C17 C13 C14 119.7(3)
C17 C13 C12 119.2(3)
C14 C13 C12 121.1(4)
C15 C14 C13 120.9(4)
C14 C15 C015 119.6(4)
C16 C015 C15 120.5(4)
C015 C16 C17 121.5(4)
C16 C17 C13 117.7(4)
C16 C17 C18 123.3(3)
C13 C17 C18 118.9(3)
C23 C18 C19 117.6(3)
C23 C18 C17 120.1(3)
C19 C18 C17 122.3(3)
C20 C19 C18 122.0(4)
C19 C20 C21 120.0(4)
C22 C21 O1 125.1(4)
C22 C21 C20 120.3(4)
O1 C21 C20 114.6(3)
C21 C22 C23 120.5(3)
C18 C23 C22 119.6(3)
C18 C23 C11 119.5(3)
C22 C23 C11 120.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C24 O1 1.424(5)
O1 C21 1.361(5)
C1 C4 1.494(5)
C2 C4 1.518(6)
C3 C4 1.518(7)
C4 C5 1.530(5)
C5 C6 1.350(6)
C5 C10 1.387(5)
C6 C7 1.383(6)
C7 C8 1.355(5)
C8 C9 1.367(5)
C8 C11 1.487(5)
C9 C10 1.379(6)
C11 C12 1.354(5)
C11 C23 1.454(5)
C12 C13 1.423(5)
C13 C17 1.407(5)
C13 C14 1.403(5)
C14 C15 1.368(6)
C15 C015 1.388(6)
C015 C16 1.363(6)
C16 C17 1.405(5)
C17 C18 1.452(5)
C18 C23 1.409(5)
C18 C19 1.414(5)
C19 C20 1.348(6)
C20 C21 1.394(5)
C21 C22 1.365(5)
C22 C23 1.406(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139193117
