#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/35/1553558.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_1553558
loop_
_publ_author_name
'Sreenivasulu, Chinnabattigalla'
'Gopi Krishna Reddy, A.'
'Satyanarayana, G.'
_publ_section_title
;
 Oxidative annulations triggered by a simple Lewis acid: facile synthesis
 of benzofurans
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              972
_journal_paper_doi               10.1039/C6QO00531D
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_compound_source        'Synthesized compound'
_chemical_formula_moiety         'C20 H14 O'
_chemical_formula_sum            'C20 H14 O'
_chemical_formula_weight         270.33
_chemical_name_systematic        2,3-diphenylbenzofuran
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-05-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-05-11 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9447(3)
_cell_length_b                   10.3826(4)
_cell_length_c                   17.0108(7)
_cell_measurement_reflns_used    1455
_cell_measurement_temperature    300
_cell_measurement_theta_max      71.2827
_cell_measurement_theta_min      4.2547
_cell_volume                     1403.16(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.9614
_diffrn_measured_fraction_theta_max 0.8614
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   -4.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  120.0000  -61.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -97.00  -41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -19.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
  5 omega   82.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.1393  154.0000  -83.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega  137.00  166.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786   63.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega   46.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -25.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786 -111.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  9 omega   68.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   54.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -25.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 12 omega   43.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
 13 omega   43.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -50.0000    0.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0431598000
_diffrn_orient_matrix_UB_12      0.1068620000
_diffrn_orient_matrix_UB_13      -0.0595256000
_diffrn_orient_matrix_UB_21      -0.1878291000
_diffrn_orient_matrix_UB_22      -0.0124635000
_diffrn_orient_matrix_UB_23      0.0213047000
_diffrn_orient_matrix_UB_31      0.0221751000
_diffrn_orient_matrix_UB_32      0.1021360000
_diffrn_orient_matrix_UB_33      0.0648159000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3193
_diffrn_reflns_theta_full        71.4234
_diffrn_reflns_theta_max         71.42
_diffrn_reflns_theta_min         4.99
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2796
_exptl_crystal_description       block
_exptl_crystal_F_000             569.6775
_exptl_crystal_preparation       synthesized
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.1550
_refine_diff_density_min         -0.2508
_refine_diff_density_rms         0.0566
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.3(7)
_refine_ls_d_res_high            0.8133
_refine_ls_d_res_low             8.8623
_refine_ls_goodness_of_fit_ref   1.0451
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0451
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0710P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.694
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                2022
_reflns_number_total             2350
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6qo00531d2.cif
_cod_data_source_block           exp_6157
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1553558
_chemical_oxdiff_formula         'C22 H15 O2'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C5(H5), C4(H4), C14(H14), C13(H13), C12(H12), C11(H11),
 C10(H10), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_olex2_exptl_crystal_mounting_method recrystalized
_olex2_submission_original_sample_id 'C B SRINIVAS'
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method
'mixture of dichloromethane and hexane'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,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_refinement_flags_posn
O1 O -0.7085(2) -0.43085(18) -0.85285(9) 0.0460(4) Uani 1.000000 .
C1 C -0.7203(3) -0.4292(3) -0.77056(13) 0.0416(5) Uani 1.000000 .
C9 C -0.8807(3) -0.4786(2) -0.74146(14) 0.0412(5) Uani 1.000000 .
C2 C -0.5779(3) -0.3815(2) -0.73786(13) 0.0404(5) Uani 1.000000 .
C4 C -0.3009(3) -0.3046(3) -0.80933(15) 0.0484(6) Uani 1.000000 .
C3 C -0.4652(3) -0.3500(2) -0.80268(14) 0.0411(5) Uani 1.000000 .
C5 C -0.2327(4) -0.2918(3) -0.88342(18) 0.0571(7) Uani 1.000000 .
C15 C -0.5342(3) -0.3651(2) -0.65381(13) 0.0415(6) Uani 1.000000 .
C8 C -0.5516(3) -0.3821(3) -0.87053(14) 0.0440(6) Uani 1.000000 .
C20 C -0.5568(3) -0.4641(3) -0.59960(14) 0.0464(6) Uani 1.000000 .
C16 C -0.4602(4) -0.2507(3) -0.62864(15) 0.0527(7) Uani 1.000000 .
C17 C -0.4076(4) -0.2369(3) -0.55187(16) 0.0650(8) Uani 1.000000 .
C10 C -0.9739(3) -0.5639(3) -0.78687(15) 0.0503(6) Uani 1.000000 .
C14 C -0.9440(3) -0.4416(3) -0.66823(15) 0.0483(6) Uani 1.000000 .
C13 C -1.0966(3) -0.4909(3) -0.64160(17) 0.0549(7) Uani 1.000000 .
C11 C -1.1252(4) -0.6124(3) -0.75945(18) 0.0581(7) Uani 1.000000 .
C7 C -0.4869(4) -0.3695(3) -0.94554(15) 0.0534(7) Uani 1.000000 .
C19 C -0.5034(4) -0.4493(3) -0.52266(15) 0.0584(8) Uani 1.000000 .
C6 C -0.3249(4) -0.3218(3) -0.95033(16) 0.0578(8) Uani 1.000000 .
C12 C -1.1858(4) -0.5768(3) -0.68708(18) 0.0585(7) Uani 1.000000 .
C18 C -0.4280(4) -0.3357(3) -0.49882(17) 0.0667(9) Uani 1.000000 .
H7 H -0.5486(4) -0.3918(3) -0.98998(15) 0.0641(8) Uiso 1.000000 R
H6 H -0.2764(4) -0.3094(3) -0.99953(16) 0.0694(9) Uiso 1.000000 R
H5 H -0.1227(4) -0.2624(3) -0.88871(18) 0.0685(9) Uiso 1.000000 R
H4 H -0.2386(3) -0.2834(3) -0.76486(15) 0.0581(7) Uiso 1.000000 R
H14 H -0.8840(3) -0.3838(3) -0.63722(15) 0.0580(7) Uiso 1.000000 R
H13 H -1.1385(3) -0.4658(3) -0.59291(17) 0.0658(8) Uiso 1.000000 R
H12 H -1.2869(4) -0.6106(3) -0.66881(18) 0.0702(9) Uiso 1.000000 R
H11 H -1.1864(4) -0.6696(3) -0.79035(18) 0.0697(9) Uiso 1.000000 R
H10 H -0.9344(3) -0.5885(3) -0.83608(15) 0.0603(8) Uiso 1.000000 R
H16 H -0.4462(4) -0.1831(3) -0.66390(15) 0.0632(8) Uiso 1.000000 R
H17 H -0.3580(4) -0.1602(3) -0.53583(16) 0.0779(10) Uiso 1.000000 R
H18 H -0.3913(4) -0.3261(3) -0.44723(17) 0.0801(10) Uiso 1.000000 R
H19 H -0.5183(4) -0.5160(3) -0.48683(15) 0.0701(9) Uiso 1.000000 R
H20 H -0.6080(3) -0.5405(3) -0.61515(14) 0.0557(7) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 O1 C1 105.87(19)
C9 C1 O1 113.1(2)
C2 C1 O1 111.0(2)
C2 C1 C9 135.9(2)
C10 C9 C1 120.1(2)
C14 C9 C1 121.3(2)
C14 C9 C10 118.7(2)
C3 C2 C1 106.5(2)
C15 C2 C1 129.4(2)
C15 C2 C3 124.1(2)
C5 C4 C3 118.4(3)
H4 C4 C3 120.81(16)
H4 C4 C5 120.81(17)
C4 C3 C2 135.5(2)
C8 C3 C2 105.8(2)
C8 C3 C4 118.6(2)
C6 C5 C4 121.4(3)
H5 C5 C4 119.32(17)
H5 C5 C6 119.32(17)
C20 C15 C2 121.6(2)
C16 C15 C2 119.6(2)
C16 C15 C20 118.7(2)
C3 C8 O1 110.8(2)
C7 C8 O1 124.9(2)
C7 C8 C3 124.3(3)
C19 C20 C15 120.3(3)
H20 C20 C15 119.85(15)
H20 C20 C19 119.85(17)
C17 C16 C15 120.5(3)
H16 C16 C15 119.74(15)
H16 C16 C17 119.74(19)
C18 C17 C16 120.6(3)
H17 C17 C16 119.72(19)
H17 C17 C18 119.72(18)
C11 C10 C9 120.5(3)
H10 C10 C9 119.75(15)
H10 C10 C11 119.75(18)
C13 C14 C9 120.1(3)
H14 C14 C9 119.93(15)
H14 C14 C13 119.93(17)
C12 C13 C14 120.2(3)
H13 C13 C14 119.88(17)
H13 C13 C12 119.88(17)
C12 C11 C10 120.6(3)
H11 C11 C10 119.71(18)
H11 C11 C12 119.71(17)
C6 C7 C8 115.7(3)
H7 C7 C8 122.13(17)
H7 C7 C6 122.13(17)
C18 C19 C20 120.3(3)
H19 C19 C20 119.85(17)
H19 C19 C18 119.85(18)
C7 C6 C5 121.6(3)
H6 C6 C5 119.22(17)
H6 C6 C7 119.22(17)
C11 C12 C13 119.8(3)
H12 C12 C13 120.08(17)
H12 C12 C11 120.08(17)
C19 C18 C17 119.6(3)
H18 C18 C17 120.20(18)
H18 C18 C19 120.20(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.403(3)
O1 C8 1.379(3)
C1 C9 1.460(3)
C1 C2 1.354(3)
C9 C10 1.389(3)
C9 C14 1.397(3)
C2 C3 1.458(3)
C2 C15 1.481(3)
C4 C3 1.392(4)
C4 C5 1.378(4)
C4 H4 0.9300
C3 C8 1.383(3)
C5 C6 1.389(4)
C5 H5 0.9300
C15 C20 1.392(3)
C15 C16 1.392(3)
C8 C7 1.382(3)
C20 C19 1.385(4)
C20 H20 0.9300
C16 C17 1.379(3)
C16 H16 0.9300
C17 C18 1.375(4)
C17 H17 0.9300
C10 C11 1.385(4)
C10 H10 0.9300
C14 C13 1.392(4)
C14 H14 0.9300
C13 C12 1.377(4)
C13 H13 0.9300
C11 C12 1.372(4)
C11 H11 0.9300
C7 C6 1.382(4)
C7 H7 0.9300
C19 C18 1.384(4)
C19 H19 0.9300
C6 H6 0.9300
C12 H12 0.9300
C18 H18 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 253613
