#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:43:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178440 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/61/4026146.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_4026146
loop_
_publ_author_name
'Ying Cheng'
'Jiang-Hua Peng'
'Yong-Jia Li'
'Xun-Yu Shi'
'Ming-Sheng Tang'
'Tian-Yu Tan'
_publ_section_title
;
 N-Heterocyclic Carbene Catalyzed Reaction of Phthalaldehydes:
 Controllable Stereoselective Synthesis of Polyhydroxylated Spiro- and
 Fused Indenones Dictated by the Structure of NHC Catalysts
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1844
_journal_page_last               1851
_journal_paper_doi               10.1021/jo102582a
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C16 H12 O4'
_chemical_formula_sum            'C16 H12 O4'
_chemical_formula_weight         268.26
_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                 94.353(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0764(8)
_cell_length_b                   19.5907(3)
_cell_length_c                   8.9411(10)
_cell_measurement_reflns_used    3286
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.9
_cell_volume                     1235.9(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear(Rigaku/MSC Inc., 2005)'
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Saturn CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12365
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         3.56
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0399
_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)+(0.0444P)²+0.4497P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                2556
_reflns_number_total             2938
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102582a_si_004.cif
_cod_data_source_block           shelxl
_cod_database_code               4026146
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
O1 O 0.74072(13) 0.53593(4) 0.62068(10) 0.0210(2) Uani 1 1 d .
H1 H 0.851(3) 0.5607(11) 0.642(2) 0.061(6) Uiso 1 1 d .
O2 O 0.49401(14) 0.62707(5) 0.51432(9) 0.0216(2) Uani 1 1 d .
H2 H 0.572(3) 0.5957(10) 0.485(2) 0.047(5) Uiso 1 1 d .
O3 O 0.14173(13) 0.57232(4) 0.54871(10) 0.0214(2) Uani 1 1 d .
H3 H 0.192(3) 0.5401(11) 0.488(2) 0.050(6) Uiso 1 1 d .
O4 O -0.00105(14) 0.62345(5) 0.80743(14) 0.0356(3) Uani 1 1 d .
C1 C 0.61423(16) 0.55610(6) 0.73017(13) 0.0159(2) Uani 1 1 d .
H1A H 0.6880 0.5756 0.8199 0.019 Uiso 1 1 calc R
C2 C 0.46531(16) 0.60986(6) 0.66421(12) 0.0146(2) Uani 1 1 d .
C3 C 0.26341(16) 0.57790(6) 0.68126(13) 0.0161(2) Uani 1 1 d .
C4 C 0.16312(17) 0.62905(6) 0.77857(14) 0.0197(3) Uani 1 1 d .
C5 C 0.49737(17) 0.49678(6) 0.77662(12) 0.0154(2) Uani 1 1 d .
C6 C 0.30438(17) 0.51001(6) 0.75687(13) 0.0157(2) Uani 1 1 d .
C7 C 0.17261(18) 0.46197(6) 0.79791(14) 0.0215(3) Uani 1 1 d .
H7 H 0.0407 0.4715 0.7865 0.026 Uiso 1 1 calc R
C8 C 0.2380(2) 0.39988(7) 0.85579(14) 0.0242(3) Uani 1 1 d .
H8 H 0.1500 0.3666 0.8843 0.029 Uiso 1 1 calc R
C9 C 0.4317(2) 0.38589(6) 0.87252(14) 0.0230(3) Uani 1 1 d .
H9 H 0.4742 0.3427 0.9101 0.028 Uiso 1 1 calc R
C10 C 0.56306(19) 0.43439(6) 0.83477(13) 0.0196(3) Uani 1 1 d .
H10 H 0.6951 0.4252 0.8483 0.024 Uiso 1 1 calc R
C11 C 0.46508(16) 0.67432(5) 0.75767(12) 0.0141(2) Uani 1 1 d .
C12 C 0.29417(17) 0.68493(6) 0.82092(13) 0.0161(2) Uani 1 1 d .
C13 C 0.26229(18) 0.74212(6) 0.90883(14) 0.0196(3) Uani 1 1 d .
H13 H 0.1437 0.7491 0.9497 0.024 Uiso 1 1 calc R
C14 C 0.40925(18) 0.78823(6) 0.93441(14) 0.0209(3) Uani 1 1 d .
H14 H 0.3917 0.8277 0.9935 0.025 Uiso 1 1 calc R
C15 C 0.58358(18) 0.77727(6) 0.87411(14) 0.0205(3) Uani 1 1 d .
H15 H 0.6836 0.8091 0.8945 0.025 Uiso 1 1 calc R
C16 C 0.61290(17) 0.72060(6) 0.78483(13) 0.0181(3) Uani 1 1 d .
H16 H 0.7311 0.7137 0.7434 0.022 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 H1 106.2(14)
C2 O2 H2 104.9(13)
C3 O3 H3 108.3(12)
O1 C1 C5 111.18(9)
O1 C1 C2 111.38(9)
C5 C1 C2 104.73(9)
O1 C1 H1A 109.8
C5 C1 H1A 109.8
C2 C1 H1A 109.8
O2 C2 C11 109.33(9)
O2 C2 C1 112.05(9)
C11 C2 C1 112.35(9)
O2 C2 C3 112.53(9)
C11 C2 C3 103.81(9)
C1 C2 C3 106.50(9)
O3 C3 C6 113.00(9)
O3 C3 C4 104.30(9)
C6 C3 C4 113.72(10)
O3 C3 C2 116.59(10)
C6 C3 C2 104.37(9)
C4 C3 C2 104.87(9)
O4 C4 C12 127.56(11)
O4 C4 C3 123.52(11)
C12 C4 C3 108.85(10)
C6 C5 C10 120.53(11)
C6 C5 C1 112.16(10)
C10 C5 C1 127.31(11)
C5 C6 C7 120.79(11)
C5 C6 C3 112.03(10)
C7 C6 C3 127.10(11)
C8 C7 C6 118.64(12)
C8 C7 H7 120.7
C6 C7 H7 120.7
C7 C8 C9 120.64(12)
C7 C8 H8 119.7
C9 C8 H8 119.7
C10 C9 C8 120.66(11)
C10 C9 H9 119.7
C8 C9 H9 119.7
C9 C10 C5 118.70(12)
C9 C10 H10 120.6
C5 C10 H10 120.6
C12 C11 C16 119.85(10)
C12 C11 C2 112.76(10)
C16 C11 C2 127.40(11)
C11 C12 C13 122.13(11)
C11 C12 C4 109.66(10)
C13 C12 C4 128.20(11)
C14 C13 C12 117.73(11)
C14 C13 H13 121.1
C12 C13 H13 121.1
C13 C14 C15 120.64(11)
C13 C14 H14 119.7
C15 C14 H14 119.7
C16 C15 C14 121.15(11)
C16 C15 H15 119.4
C14 C15 H15 119.4
C11 C16 C15 118.48(11)
C11 C16 H16 120.8
C15 C16 H16 120.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4313(14)
O1 H1 0.93(2)
O2 C2 1.4115(14)
O2 H2 0.88(2)
O3 C3 1.4152(14)
O3 H3 0.92(2)
O4 C4 1.2139(15)
C1 C5 1.5030(16)
C1 C2 1.5726(16)
C1 H1A 1.0000
C2 C11 1.5144(15)
C2 C3 1.5778(16)
C3 C6 1.5101(16)
C3 C4 1.5358(16)
C4 C12 1.4657(16)
C5 C6 1.3881(17)
C5 C10 1.3942(16)
C6 C7 1.3935(17)
C7 C8 1.3877(18)
C7 H7 0.9500
C8 C9 1.395(2)
C8 H8 0.9500
C9 C10 1.3886(18)
C9 H9 0.9500
C10 H10 0.9500
C11 C12 1.3891(16)
C11 C16 1.3916(16)
C12 C13 1.3967(16)
C13 C14 1.3834(17)
C13 H13 0.9500
C14 C15 1.3999(18)
C14 H14 0.9500
C15 C16 1.3920(16)
C15 H15 0.9500
C16 H16 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.93(2) 2.14(2) 2.9331(14) 143.3(19) 1_655
O1 H1 O3 0.93(2) 2.29(2) 3.0417(13) 138.3(18) 1_655
O2 H2 O1 0.88(2) 2.01(2) 2.6245(13) 125.6(17) .
O3 H3 O1 0.92(2) 1.86(2) 2.7703(13) 169.1(18) 3_666
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
O1 C1 C2 O2 -1.61(13)
C5 C1 C2 O2 -121.88(10)
O1 C1 C2 C11 -125.16(10)
C5 C1 C2 C11 114.57(10)
O1 C1 C2 C3 121.83(10)
C5 C1 C2 C3 1.56(11)
O2 C2 C3 O3 -1.13(14)
C11 C2 C3 O3 116.96(10)
C1 C2 C3 O3 -124.28(10)
O2 C2 C3 C6 124.27(10)
C11 C2 C3 C6 -117.64(9)
C1 C2 C3 C6 1.13(11)
O2 C2 C3 C4 -115.88(10)
C11 C2 C3 C4 2.21(11)
C1 C2 C3 C4 120.97(10)
O3 C3 C4 O4 52.08(16)
C6 C3 C4 O4 -71.46(16)
C2 C3 C4 O4 175.14(12)
O3 C3 C4 C12 -125.09(10)
C6 C3 C4 C12 111.38(11)
C2 C3 C4 C12 -2.02(12)
O1 C1 C5 C6 -124.46(10)
C2 C1 C5 C6 -4.06(12)
O1 C1 C5 C10 56.07(15)
C2 C1 C5 C10 176.47(11)
C10 C5 C6 C7 1.51(17)
C1 C5 C6 C7 -178.01(10)
C10 C5 C6 C3 -175.38(10)
C1 C5 C6 C3 5.10(13)
O3 C3 C6 C5 123.88(11)
C4 C3 C6 C5 -117.46(11)
C2 C3 C6 C5 -3.76(12)
O3 C3 C6 C7 -52.77(16)
C4 C3 C6 C7 65.89(15)
C2 C3 C6 C7 179.59(11)
C5 C6 C7 C8 -1.48(18)
C3 C6 C7 C8 174.91(11)
C6 C7 C8 C9 0.01(19)
C7 C8 C9 C10 1.46(19)
C8 C9 C10 C5 -1.43(18)
C6 C5 C10 C9 -0.04(17)
C1 C5 C10 C9 179.40(11)
O2 C2 C11 C12 118.51(11)
C1 C2 C11 C12 -116.44(11)
C3 C2 C11 C12 -1.78(12)
O2 C2 C11 C16 -62.05(15)
C1 C2 C11 C16 63.00(15)
C3 C2 C11 C16 177.67(11)
C16 C11 C12 C13 1.83(18)
C2 C11 C12 C13 -178.68(11)
C16 C11 C12 C4 -178.95(10)
C2 C11 C12 C4 0.55(14)
O4 C4 C12 C11 -176.02(14)
C3 C4 C12 C11 0.99(14)
O4 C4 C12 C13 3.1(2)
C3 C4 C12 C13 -179.84(11)
C11 C12 C13 C14 -1.27(18)
C4 C12 C13 C14 179.65(12)
C12 C13 C14 C15 -0.23(19)
C13 C14 C15 C16 1.19(19)
C12 C11 C16 C15 -0.83(17)
C2 C11 C16 C15 179.76(11)
C14 C15 C16 C11 -0.64(18)
