#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:40:02 +0200 (mar 06 de oct de 2020) $
#$Revision: 257894 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/93/7059372.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_7059372
loop_
_publ_author_name
'Rahmatpour, Ali'
_publ_section_title
;
 Regioselective condensation of hydroxyaromatic compounds with
 2,5-dimethoxytetrahydrofuran: facile one-pot synthesis of new substituted
 diaryl-fused 2,8-dioxabicyclo[3.3.2]nonanes comprising central ketal
 moieties
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4834
_journal_page_last               4841
_journal_paper_doi               10.1039/C9NJ06232G
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C18 H16 Cl2 O2'
_chemical_formula_sum            'C18 H16 Cl2 O2'
_chemical_formula_weight         335.21
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-12-17 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.398(5)
_cell_length_b                   9.4469(19)
_cell_length_c                   7.4776(15)
_cell_measurement_reflns_used    2777
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.34
_cell_volume                     1582.2(6)
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_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  0.0685
_diffrn_reflns_av_sigmaI/netI    0.0685
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8395
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.8519
_exptl_absorpt_correction_T_min  0.8197
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.894
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0293P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0750
_reflns_number_gt                1848
_reflns_number_total             2777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9nj06232g2.cif
_cod_data_source_block           khd598h
_cod_depositor_comments
;Adding full bibliography for 7059372.cif.

 Adding full bibliography for 7059372.cif.
;
_cod_database_code               7059372
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.56765(4) 0.30153(12) 0.87745(14) 0.0766(3) Uani 1 1 d . . .
Cl2 Cl 0.92182(4) 0.27442(11) 1.03914(13) 0.0762(3) Uani 1 1 d . . .
O1 O 0.71441(11) 0.2228(2) 0.2389(3) 0.0615(7) Uani 1 1 d . . .
O2 O 0.79776(9) 0.3352(2) 0.3553(3) 0.0571(6) Uani 1 1 d . . .
C1 C 0.53042(16) 0.3899(5) 0.4955(6) 0.0832(14) Uani 1 1 d . . .
H1A H 0.5264 0.4184 0.3729 0.125 Uiso 1 1 calc R . .
H1B H 0.5269 0.4714 0.5716 0.125 Uiso 1 1 calc R . .
H1C H 0.4996 0.3232 0.5246 0.125 Uiso 1 1 calc R . .
C2 C 0.59060(14) 0.3222(3) 0.5229(6) 0.0570(10) Uani 1 1 d . . .
C3 C 0.61076(15) 0.2744(4) 0.6853(5) 0.0492(9) Uani 1 1 d . . .
C4 C 0.66471(13) 0.2073(3) 0.7041(5) 0.0444(8) Uani 1 1 d . . .
H4 H 0.6764 0.1765 0.8169 0.053 Uiso 1 1 calc R . .
C5 C 0.70223(13) 0.1843(3) 0.5603(4) 0.0414(8) Uani 1 1 d . . .
C6 C 0.68324(14) 0.2366(3) 0.3955(5) 0.0472(8) Uani 1 1 d . . .
C7 C 0.62819(14) 0.3027(4) 0.3808(6) 0.0544(9) Uani 1 1 d . . .
H7 H 0.6162 0.3353 0.2691 0.065 Uiso 1 1 calc R . .
C8 C 0.77746(17) 0.2238(4) 0.2426(5) 0.0573(10) Uani 1 1 d . . .
H8 H 0.7902 0.2491 0.1213 0.069 Uiso 1 1 calc R . .
C9 C 0.80418(17) 0.0801(4) 0.2797(5) 0.0664(11) Uani 1 1 d . . .
H9A H 0.8463 0.0913 0.3062 0.080 Uiso 1 1 calc R . .
H9B H 0.8009 0.0223 0.1729 0.080 Uiso 1 1 calc R . .
C10 C 0.77424(16) 0.0034(3) 0.4346(4) 0.0547(9) Uani 1 1 d . . .
H10A H 0.8003 -0.0714 0.4768 0.066 Uiso 1 1 calc R . .
H10B H 0.7375 -0.0399 0.3928 0.066 Uiso 1 1 calc R . .
C11 C 0.76005(13) 0.1035(3) 0.5896(4) 0.0457(8) Uani 1 1 d . . .
H11 H 0.7541 0.0442 0.6957 0.055 Uiso 1 1 calc R . .
C12 C 0.81129(14) 0.2019(4) 0.6310(5) 0.0457(8) Uani 1 1 d . . .
C13 C 0.82798(14) 0.3088(4) 0.5114(5) 0.0477(9) Uani 1 1 d . . .
C14 C 0.87428(14) 0.3992(3) 0.5538(5) 0.0559(9) Uani 1 1 d . . .
H14 H 0.8853 0.4676 0.4706 0.067 Uiso 1 1 calc R . .
C15 C 0.90481(14) 0.3932(4) 0.7131(5) 0.0561(9) Uani 1 1 d . . .
C16 C 0.95463(15) 0.4961(4) 0.7535(6) 0.0824(13) Uani 1 1 d . . .
H16A H 0.9905 0.4446 0.7796 0.124 Uiso 1 1 calc R . .
H16B H 0.9439 0.5530 0.8550 0.124 Uiso 1 1 calc R . .
H16C H 0.9611 0.5561 0.6518 0.124 Uiso 1 1 calc R . .
C17 C 0.88780(14) 0.2876(4) 0.8301(5) 0.0523(9) Uani 1 1 d . . .
C18 C 0.84300(13) 0.1923(3) 0.7885(4) 0.0469(9) Uani 1 1 d . . .
H18 H 0.8341 0.1200 0.8686 0.056 Uiso 1 1 calc R . .
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
C6 O1 C8 119.5(3) . . ?
C13 O2 C8 121.8(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 116.1(3) . . ?
C7 C2 C1 120.1(4) . . ?
C3 C2 C1 123.7(4) . . ?
C2 C3 C4 122.2(3) . . ?
C2 C3 Cl1 119.8(3) . . ?
C4 C3 Cl1 118.0(3) . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 116.5(3) . . ?
C4 C5 C11 119.0(3) . . ?
C6 C5 C11 124.4(3) . . ?
O1 C6 C7 115.4(3) . . ?
O1 C6 C5 124.5(3) . . ?
C7 C6 C5 120.1(3) . . ?
C2 C7 C6 123.1(4) . . ?
C2 C7 H7 118.4 . . ?
C6 C7 H7 118.4 . . ?
O1 C8 O2 109.6(3) . . ?
O1 C8 C9 113.2(3) . . ?
O2 C8 C9 115.5(3) . . ?
O1 C8 H8 105.9 . . ?
O2 C8 H8 105.9 . . ?
C9 C8 H8 105.9 . . ?
C8 C9 C10 113.2(3) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 112.0(3) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C5 111.6(3) . . ?
C12 C11 C10 112.2(3) . . ?
C5 C11 C10 112.3(3) . . ?
C12 C11 H11 106.8 . . ?
C5 C11 H11 106.8 . . ?
C10 C11 H11 106.8 . . ?
C18 C12 C13 117.1(3) . . ?
C18 C12 C11 121.8(3) . . ?
C13 C12 C11 121.1(3) . . ?
O2 C13 C14 116.9(3) . . ?
O2 C13 C12 122.9(3) . . ?
C14 C13 C12 120.0(3) . . ?
C15 C14 C13 123.2(3) . . ?
C15 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
C14 C15 C17 116.2(3) . . ?
C14 C15 C16 120.9(3) . . ?
C17 C15 C16 122.8(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 C18 121.8(3) . . ?
C15 C17 Cl2 119.9(3) . . ?
C18 C17 Cl2 118.2(3) . . ?
C12 C18 C17 121.5(3) . . ?
C12 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
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
Cl1 C3 1.750(3) . ?
Cl2 C17 1.743(4) . ?
O1 C6 1.370(4) . ?
O1 C8 1.413(4) . ?
O2 C13 1.372(4) . ?
O2 C8 1.423(4) . ?
C1 C2 1.506(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.368(5) . ?
C2 C3 1.372(5) . ?
C3 C4 1.372(4) . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(5) . ?
C5 C11 1.519(4) . ?
C6 C7 1.386(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.509(5) . ?
C8 H8 0.9800 . ?
C9 C10 1.522(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.529(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.509(5) . ?
C11 H11 0.9800 . ?
C12 C18 1.378(4) . ?
C12 C13 1.400(4) . ?
C13 C14 1.381(4) . ?
C14 C15 1.374(5) . ?
C14 H14 0.9300 . ?
C15 C17 1.381(5) . ?
C15 C16 1.511(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.384(4) . ?
C18 H18 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 -1.7(5) . . . . ?
C1 C2 C3 C4 176.9(3) . . . . ?
C7 C2 C3 Cl1 177.0(2) . . . . ?
C1 C2 C3 Cl1 -4.3(5) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
Cl1 C3 C4 C5 -178.5(2) . . . . ?
C3 C4 C5 C6 1.9(4) . . . . ?
C3 C4 C5 C11 -177.3(3) . . . . ?
C8 O1 C6 C7 149.3(3) . . . . ?
C8 O1 C6 C5 -33.4(4) . . . . ?
C4 C5 C6 O1 -179.6(3) . . . . ?
C11 C5 C6 O1 -0.5(5) . . . . ?
C4 C5 C6 C7 -2.4(4) . . . . ?
C11 C5 C6 C7 176.6(3) . . . . ?
C3 C2 C7 C6 1.1(5) . . . . ?
C1 C2 C7 C6 -177.6(3) . . . . ?
O1 C6 C7 C2 178.4(3) . . . . ?
C5 C6 C7 C2 1.0(5) . . . . ?
C6 O1 C8 O2 -45.0(4) . . . . ?
C6 O1 C8 C9 85.5(4) . . . . ?
C13 O2 C8 O1 114.5(3) . . . . ?
C13 O2 C8 C9 -14.8(4) . . . . ?
O1 C8 C9 C10 -46.3(5) . . . . ?
O2 C8 C9 C10 81.2(4) . . . . ?
C8 C9 C10 C11 -40.7(4) . . . . ?
C4 C5 C11 C12 -91.9(3) . . . . ?
C6 C5 C11 C12 89.0(4) . . . . ?
C4 C5 C11 C10 141.1(3) . . . . ?
C6 C5 C11 C10 -38.0(4) . . . . ?
C9 C10 C11 C12 -44.3(4) . . . . ?
C9 C10 C11 C5 82.3(3) . . . . ?
C5 C11 C12 C18 120.6(3) . . . . ?
C10 C11 C12 C18 -112.4(3) . . . . ?
C5 C11 C12 C13 -58.4(4) . . . . ?
C10 C11 C12 C13 68.6(4) . . . . ?
C8 O2 C13 C14 141.8(3) . . . . ?
C8 O2 C13 C12 -42.5(4) . . . . ?
C18 C12 C13 O2 -175.9(3) . . . . ?
C11 C12 C13 O2 3.1(5) . . . . ?
C18 C12 C13 C14 -0.3(5) . . . . ?
C11 C12 C13 C14 178.8(3) . . . . ?
O2 C13 C14 C15 174.0(3) . . . . ?
C12 C13 C14 C15 -1.9(5) . . . . ?
C13 C14 C15 C17 1.7(5) . . . . ?
C13 C14 C15 C16 -179.2(3) . . . . ?
C14 C15 C17 C18 0.7(5) . . . . ?
C16 C15 C17 C18 -178.4(3) . . . . ?
C14 C15 C17 Cl2 -177.7(2) . . . . ?
C16 C15 C17 Cl2 3.2(5) . . . . ?
C13 C12 C18 C17 2.6(4) . . . . ?
C11 C12 C18 C17 -176.4(3) . . . . ?
C15 C17 C18 C12 -2.9(5) . . . . ?
Cl2 C17 C18 C12 175.5(2) . . . . ?
