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#$Date: 2017-02-04 16:14:51 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191748 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/54/7155433.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_7155433
loop_
_publ_author_name
'Mohan Raj, Radhakrishnan'
'Balasubramanian, Kalpattu K.'
'Easwaramoorthy, Deivanayagam'
_publ_section_title
;
 Diels-Alder trapping of in situ generated dienes from
 3,4-dihydro-2H-pyran with p-quinone catalysed by p-toluenesulfonic acid.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1115
_journal_page_last               1121
_journal_paper_doi               10.1039/c6ob02006b
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C16 H20 Cl2 O4'
_chemical_formula_sum            'C16 H20 Cl2 O4'
_chemical_formula_weight         347.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2016-12-22 deposited with the CCDC.
2017-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 103.111(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            2
_cell_length_a                   5.945(5)
_cell_length_b                   18.659(5)
_cell_length_c                   7.352(5)
_cell_measurement_reflns_used    1396
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.995
_cell_measurement_theta_min      2.183
_cell_volume                     794.3(9)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6895
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.183
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0282
_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)+(0.0287P)²+0.2968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0698
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1277
_reflns_number_total             1396
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ob02006b2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7155432--7155435.cif.'
_cod_database_code               7155433
_shelx_shelxl_version_number     2016/4
_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   0.920
_shelx_estimated_absorpt_t_max   0.959
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.8915(2) 0.09488(8) 0.89227(19) 0.0345(3) Uani 1 1 d . .
H1 H 1.024512 0.069162 0.866378 0.041 Uiso 1 1 calc R U
C2 C 0.9700(3) 0.16708(9) 0.9762(2) 0.0426(4) Uani 1 1 d . .
H2A H 1.026146 0.195717 0.885652 0.051 Uiso 1 1 calc R U
H2B H 1.096248 0.160562 1.084517 0.051 Uiso 1 1 calc R U
C3 C 0.7733(3) 0.20612(8) 1.0336(2) 0.0477(4) Uani 1 1 d . .
H3A H 0.830411 0.249851 1.099458 0.057 Uiso 1 1 calc R U
H3B H 0.656304 0.218926 0.923503 0.057 Uiso 1 1 calc R U
C4 C 0.6687(3) 0.15817(9) 1.1592(2) 0.0477(4) Uani 1 1 d . .
H4A H 0.780301 0.150157 1.275937 0.057 Uiso 1 1 calc R U
H4B H 0.534375 0.181325 1.187113 0.057 Uiso 1 1 calc R U
C5 C 0.5992(3) 0.08737(9) 1.0637(2) 0.0461(4) Uani 1 1 d . .
H5A H 0.541508 0.056063 1.148083 0.055 Uiso 1 1 calc R U
H5B H 0.475144 0.095252 0.954563 0.055 Uiso 1 1 calc R U
C6 C 0.6223(2) 0.05373(7) 0.61515(18) 0.0310(3) Uani 1 1 d . .
C7 C 0.3968(2) 0.06454(7) 0.51422(19) 0.0329(3) Uani 1 1 d . .
C8 C 0.2753(3) 0.01192(8) 0.4003(2) 0.0343(3) Uani 1 1 d . .
O1 O 0.78868(18) 0.05290(5) 1.00744(14) 0.0393(3) Uani 1 1 d . .
O2 O 0.73052(17) 0.11021(5) 0.71836(13) 0.0367(3) Uani 1 1 d . .
CL1 Cl 0.26467(7) 0.14651(2) 0.53181(6) 0.05208(16) Uani 1 1 d . .
H8A H 0.126(3) 0.0217(9) 0.334(2) 0.045(5) Uiso 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'
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
O1 C1 O2 110.89(12) . .
O1 C1 C2 113.01(13) . .
O2 C1 C2 105.48(12) . .
O1 C1 H1 109.1 . .
O2 C1 H1 109.1 . .
C2 C1 H1 109.1 . .
C1 C2 C3 110.82(13) . .
C1 C2 H2A 109.5 . .
C3 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
C3 C2 H2B 109.5 . .
H2A C2 H2B 108.1 . .
C4 C3 C2 109.55(14) . .
C4 C3 H3A 109.8 . .
C2 C3 H3A 109.8 . .
C4 C3 H3B 109.8 . .
C2 C3 H3B 109.8 . .
H3A C3 H3B 108.2 . .
C5 C4 C3 109.87(14) . .
C5 C4 H4A 109.7 . .
C3 C4 H4A 109.7 . .
C5 C4 H4B 109.7 . .
C3 C4 H4B 109.7 . .
H4A C4 H4B 108.2 . .
O1 C5 C4 112.10(13) . .
O1 C5 H5A 109.2 . .
C4 C5 H5A 109.2 . .
O1 C5 H5B 109.2 . .
C4 C5 H5B 109.2 . .
H5A C5 H5B 107.9 . .
O2 C6 C8 124.47(13) . 3_656
O2 C6 C7 117.26(13) . .
C8 C6 C7 118.22(13) 3_656 .
C8 C7 C6 121.83(13) . .
C8 C7 CL1 119.17(12) . .
C6 C7 CL1 119.01(11) . .
C7 C8 C6 119.95(14) . 3_656
C7 C8 H8A 118.8(10) . .
C6 C8 H8A 121.2(10) 3_656 .
C1 O1 C5 113.82(12) . .
C6 O2 C1 118.19(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.3923(18) .
C1 O2 1.4412(18) .
C1 C2 1.511(2) .
C1 H1 0.9800 .
C2 C3 1.517(2) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.516(2) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.509(2) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 O1 1.437(2) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 O2 1.3707(17) .
C6 C8 1.384(2) 3_656
C6 C7 1.392(2) .
C7 C8 1.383(2) .
C7 CL1 1.7374(15) .
C8 C6 1.384(2) 3_656
C8 H8A 0.929(17) .
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_4
O1 C1 C2 C3 -53.61(17) . .
O2 C1 C2 C3 67.69(16) . .
C1 C2 C3 C4 53.19(17) . .
C2 C3 C4 C5 -54.33(18) . .
C3 C4 C5 O1 55.36(19) . .
O2 C6 C7 C8 177.58(13) . .
C8 C6 C7 C8 -0.2(2) 3_656 .
O2 C6 C7 CL1 -2.34(17) . .
C8 C6 C7 CL1 179.90(11) 3_656 .
C6 C7 C8 C6 0.2(2) . 3_656
CL1 C7 C8 C6 -179.90(11) . 3_656
O2 C1 O1 C5 -63.33(15) . .
C2 C1 O1 C5 54.85(16) . .
C4 C5 O1 C1 -56.08(18) . .
C8 C6 O2 C1 -36.25(19) 3_656 .
C7 C6 O2 C1 146.15(13) . .
O1 C1 O2 C6 -54.36(16) . .
C2 C1 O2 C6 -177.02(12) . .
