#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:50:45 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180237 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/23/7112356.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_7112356
loop_
_publ_author_name
'Chen, Mu-Wang'
'Cao, Liang-Liang'
'Ye, Zhi-Shi'
'Jiang, Guo-Fang'
'Zhou, Yong-Gui'
_publ_section_title
;
 A mild method for generation of o-quinone methides under basic
 conditions. The facile synthesis of trans-2,3-dihydrobenzofurans.
;
_journal_issue                   16
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1660
_journal_page_last               1662
_journal_paper_doi               10.1039/c3cc37800d
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C17 H16 O3'
_chemical_formula_weight         268.30
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.935(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7194(11)
_cell_length_b                   8.3104(10)
_cell_length_c                   17.6639(19)
_cell_measurement_reflns_used    2152
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.800
_cell_measurement_theta_min      4.657
_cell_volume                     1413.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8256
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59954
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.176
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0515
_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)+(0.0695P)²+0.3241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1509
_reflns_number_gt                1966
_reflns_number_total             2771
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7108862
_cod_data_source_file            c3cc37800d.txt
_cod_data_source_block           cd212150
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7112356
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.51059(13) 0.5945(2) 0.08084(7) 0.0739(5) Uani 1 1 d . A .
O2 O 0.41870(15) 0.8102(3) -0.02815(10) 0.1082(7) Uani 1 1 d . . .
O3 O 0.61920(15) 0.8013(3) -0.07416(9) 0.0931(6) Uani 1 1 d D . .
C1 C 0.55282(18) 0.6242(3) 0.15671(10) 0.0592(5) Uani 1 1 d . . .
C2 C 0.48436(19) 0.5680(3) 0.21428(12) 0.0729(6) Uani 1 1 d . . .
H2 H 0.4039 0.5066 0.2040 0.087 Uiso 1 1 calc R . .
C3 C 0.5404(2) 0.6067(3) 0.28814(12) 0.0784(7) Uani 1 1 d . . .
H3 H 0.4971 0.5705 0.3287 0.094 Uiso 1 1 calc R . .
C4 C 0.6589(2) 0.6978(3) 0.30266(11) 0.0766(6) Uani 1 1 d . . .
H4 H 0.6955 0.7212 0.3529 0.092 Uiso 1 1 calc R . .
C5 C 0.7246(2) 0.7549(3) 0.24360(11) 0.0656(6) Uani 1 1 d . . .
H5 H 0.8041 0.8179 0.2537 0.079 Uiso 1 1 calc R . .
C6 C 0.67076(17) 0.7172(2) 0.16949(10) 0.0523(4) Uani 1 1 d . . .
C7 C 0.71829(16) 0.7594(2) 0.09446(10) 0.0521(4) Uani 1 1 d . A .
H7 H 0.7041 0.8748 0.0848 0.063 Uiso 1 1 calc R . .
C8 C 0.61124(17) 0.6625(3) 0.03785(10) 0.0600(5) Uani 1 1 d . . .
H8 H 0.6596 0.5756 0.0149 0.072 Uiso 1 1 calc R A .
C9 C 0.53561(19) 0.7654(3) -0.02452(11) 0.0723(6) Uani 1 1 d . A .
C10 C 0.5658(10) 0.9409(11) -0.1273(4) 0.081(2) Uani 0.50 1 d PDU A 1
H10A H 0.4735 0.9191 -0.1538 0.097 Uiso 0.50 1 calc PR A 1
H10B H 0.5645 1.0413 -0.0993 0.097 Uiso 0.50 1 calc PR A 1
C11 C 0.6709(11) 0.9447(13) -0.1811(5) 0.114(3) Uani 0.55 1 d PDU A 1
H11A H 0.7584 0.9806 -0.1545 0.171 Uiso 0.55 1 calc PR A 1
H11B H 0.6407 1.0173 -0.2224 0.171 Uiso 0.55 1 calc PR A 1
H11C H 0.6814 0.8387 -0.2012 0.171 Uiso 0.55 1 calc PR A 1
C10' C 0.5691(13) 0.8767(13) -0.1451(6) 0.109(3) Uani 0.50 1 d PDU A 2
H10C H 0.4758 0.9171 -0.1440 0.131 Uiso 0.50 1 calc PR A 2
H10D H 0.5663 0.7994 -0.1864 0.131 Uiso 0.50 1 calc PR A 2
C11' C 0.6609(14) 1.0078(12) -0.1573(7) 0.107(3) Uani 0.45 1 d PDU A 2
H11D H 0.6669 1.0808 -0.1149 0.160 Uiso 0.45 1 calc PR A 2
H11E H 0.6252 1.0635 -0.2034 0.160 Uiso 0.45 1 calc PR A 2
H11F H 0.7516 0.9661 -0.1617 0.160 Uiso 0.45 1 calc PR A 2
C12 C 0.86736(17) 0.7165(2) 0.08675(10) 0.0540(5) Uani 1 1 d . . .
C13 C 0.9382(2) 0.8024(3) 0.03816(13) 0.0790(7) Uani 1 1 d . A .
H13 H 0.8953 0.8889 0.0110 0.095 Uiso 1 1 calc R . .
C14 C 1.0727(3) 0.7615(4) 0.02923(15) 0.0982(9) Uani 1 1 d . . .
H14 H 1.1194 0.8206 -0.0040 0.118 Uiso 1 1 calc R A .
C15 C 1.1375(2) 0.6364(4) 0.06825(15) 0.0912(9) Uani 1 1 d . A .
H15 H 1.2289 0.6108 0.0629 0.109 Uiso 1 1 calc R . .
C16 C 1.0676(2) 0.5489(4) 0.11513(15) 0.0962(8) Uani 1 1 d . . .
H16 H 1.1105 0.4611 0.1412 0.115 Uiso 1 1 calc R A .
C17 C 0.9325(2) 0.5890(3) 0.12473(13) 0.0791(7) Uani 1 1 d . A .
H17 H 0.8860 0.5282 0.1574 0.095 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C8 108.23(13)
C9 O3 C10' 121.4(5)
C9 O3 C10 113.1(4)
C10' O3 C10 23.9(5)
O1 C1 C2 123.62(17)
O1 C1 C6 113.12(16)
C2 C1 C6 123.26(18)
C1 C2 C3 116.9(2)
C1 C2 H2 121.5
C3 C2 H2 121.5
C4 C3 C2 121.1(2)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 120.81(19)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C4 119.04(19)
C6 C5 H5 120.5
C4 C5 H5 120.5
C1 C6 C5 118.86(17)
C1 C6 C7 109.69(15)
C5 C6 C7 131.45(17)
C6 C7 C12 115.96(15)
C6 C7 C8 100.68(14)
C12 C7 C8 112.41(15)
C6 C7 H7 109.1
C12 C7 H7 109.1
C8 C7 H7 109.1
O1 C8 C9 108.16(14)
O1 C8 C7 107.86(14)
C9 C8 C7 113.01(18)
O1 C8 H8 109.2
C9 C8 H8 109.2
C7 C8 H8 109.2
O2 C9 O3 124.7(2)
O2 C9 C8 125.8(2)
O3 C9 C8 109.54(16)
C11 C10 O3 101.7(7)
C11 C10 H10A 111.4
O3 C10 H10A 111.4
C11 C10 H10B 111.4
O3 C10 H10B 111.4
H10A C10 H10B 109.3
O3 C10' C11' 108.7(9)
O3 C10' H10C 110.0
C11' C10' H10C 110.0
O3 C10' H10D 110.0
C11' C10' H10D 110.0
H10C C10' H10D 108.3
C10' C11' H11D 109.5
C10' C11' H11E 109.5
H11D C11' H11E 109.5
C10' C11' H11F 109.5
H11D C11' H11F 109.5
H11E C11' H11F 109.5
C17 C12 C13 118.24(19)
C17 C12 C7 121.58(18)
C13 C12 C7 120.12(19)
C12 C13 C14 120.5(3)
C12 C13 H13 119.7
C14 C13 H13 119.7
C15 C14 C13 120.8(2)
C15 C14 H14 119.6
C13 C14 H14 119.6
C16 C15 C14 119.1(2)
C16 C15 H15 120.5
C14 C15 H15 120.5
C15 C16 C17 120.6(3)
C15 C16 H16 119.7
C17 C16 H16 119.7
C12 C17 C16 120.7(2)
C12 C17 H17 119.7
C16 C17 H17 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.369(2)
O1 C8 1.435(2)
O2 C9 1.189(2)
O3 C9 1.309(2)
O3 C10' 1.425(10)
O3 C10 1.537(9)
C1 C2 1.372(3)
C1 C6 1.375(3)
C2 C3 1.381(3)
C2 H2 0.9300
C3 C4 1.373(3)
C3 H3 0.9300
C4 C5 1.380(3)
C4 H4 0.9300
C5 C6 1.377(2)
C5 H5 0.9300
C6 C7 1.504(2)
C7 C12 1.516(2)
C7 C8 1.563(2)
C7 H7 0.9800
C8 C9 1.503(3)
C8 H8 0.9800
C10 C11 1.489(11)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C10' C11' 1.442(14)
C10' H10C 0.9700
C10' H10D 0.9700
C11' H11D 0.9600
C11' H11E 0.9600
C11' H11F 0.9600
C12 C17 1.363(3)
C12 C13 1.373(3)
C13 C14 1.381(3)
C13 H13 0.9300
C14 C15 1.354(4)
C14 H14 0.9300
C15 C16 1.353(4)
C15 H15 0.9300
C16 C17 1.387(3)
C16 H16 0.9300
C17 H17 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
C8 O1 C1 C2 -176.3(2)
C8 O1 C1 C6 4.0(2)
O1 C1 C2 C3 179.38(19)
C6 C1 C2 C3 -1.0(3)
C1 C2 C3 C4 0.2(4)
C2 C3 C4 C5 0.8(4)
C3 C4 C5 C6 -1.0(3)
O1 C1 C6 C5 -179.55(18)
C2 C1 C6 C5 0.8(3)
O1 C1 C6 C7 0.2(2)
C2 C1 C6 C7 -179.45(19)
C4 C5 C6 C1 0.2(3)
C4 C5 C6 C7 -179.5(2)
C1 C6 C7 C12 -125.43(18)
C5 C6 C7 C12 54.3(3)
C1 C6 C7 C8 -3.88(19)
C5 C6 C7 C8 175.8(2)
C1 O1 C8 C9 -128.96(18)
C1 O1 C8 C7 -6.4(2)
C6 C7 C8 O1 6.14(19)
C12 C7 C8 O1 130.16(17)
C6 C7 C8 C9 125.66(16)
C12 C7 C8 C9 -110.32(18)
C10' O3 C9 O2 -10.9(6)
C10 O3 C9 O2 14.4(5)
C10' O3 C9 C8 170.3(5)
C10 O3 C9 C8 -164.4(4)
O1 C8 C9 O2 14.5(3)
C7 C8 C9 O2 -104.9(3)
O1 C8 C9 O3 -166.69(18)
C7 C8 C9 O3 74.0(2)
C9 O3 C10 C11 -174.7(5)
C10' O3 C10 C11 -58.9(18)
C9 O3 C10' C11' 133.7(8)
C10 O3 C10' C11' 57.7(16)
C6 C7 C12 C17 29.6(3)
C8 C7 C12 C17 -85.5(2)
C6 C7 C12 C13 -153.24(19)
C8 C7 C12 C13 91.7(2)
C17 C12 C13 C14 -1.0(3)
C7 C12 C13 C14 -178.3(2)
C12 C13 C14 C15 -0.2(4)
C13 C14 C15 C16 1.5(4)
C14 C15 C16 C17 -1.6(4)
C13 C12 C17 C16 0.9(3)
C7 C12 C17 C16 178.1(2)
C15 C16 C17 C12 0.4(4)
