#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:43:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178440 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/61/4026150.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_4026150
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         'C21 H18 Br2 O5'
_chemical_formula_sum            'C21 H18 Br2 O5'
_chemical_formula_weight         510.17
_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                 94.280(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8430(10)
_cell_length_b                   23.98(3)
_cell_length_c                   10.6860(12)
_cell_measurement_reflns_used    9595
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      1.90
_cell_volume                     2515(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD camera'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31842
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.247
_exptl_absorpt_correction_T_max  0.5926
_exptl_absorpt_correction_T_min  0.5096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       prism
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_platon_squeeze_details
;
;
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0393P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                4883
_reflns_number_total             5957
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102582a_si_008.cif
_cod_data_source_block           shelxl
_cod_database_code               4026150
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
Br1 Br 0.66368(3) 0.235068(10) -0.54861(2) 0.02485(8) Uani 1 1 d .
Br2 Br 1.12843(3) 0.028970(11) 0.21234(3) 0.03842(9) Uani 1 1 d .
O1 O 0.49456(15) 0.17864(7) -0.04203(14) 0.0234(4) Uani 1 1 d .
H1 H 0.4540 0.1747 -0.1134 0.035 Uiso 1 1 calc R
O2 O 0.61551(16) 0.22208(7) 0.16118(14) 0.0196(3) Uani 1 1 d .
H2 H 0.5351 0.2226 0.1287 0.029 Uiso 1 1 calc R
O3 O 0.69712(15) 0.31573(6) 0.06035(13) 0.0171(3) Uani 1 1 d .
O4 O 0.66909(19) 0.08856(7) -0.13359(15) 0.0301(4) Uani 1 1 d .
O5 O 0.83379(16) 0.31772(7) 0.23692(14) 0.0223(4) Uani 1 1 d .
C1 C 0.6370(2) 0.18302(9) -0.05385(19) 0.0159(5) Uani 1 1 d .
C2 C 0.7061(2) 0.21188(9) 0.06721(19) 0.0157(5) Uani 1 1 d .
C3 C 0.7718(2) 0.26768(9) 0.02046(19) 0.0164(5) Uani 1 1 d .
H3 H 0.8703 0.2702 0.0504 0.020 Uiso 1 1 calc R
C4 C 0.7543(2) 0.26434(9) -0.1197(2) 0.0162(5) Uani 1 1 d .
C5 C 0.6788(2) 0.21837(9) -0.1616(2) 0.0156(5) Uani 1 1 d .
C6 C 0.6508(2) 0.20801(9) -0.28953(19) 0.0168(5) Uani 1 1 d .
H6 H 0.6000 0.1763 -0.3186 0.020 Uiso 1 1 calc R
C7 C 0.7007(2) 0.24634(10) -0.3725(2) 0.0190(5) Uani 1 1 d .
C8 C 0.7769(2) 0.29315(10) -0.3321(2) 0.0207(5) Uani 1 1 d .
H8 H 0.8087 0.3188 -0.3912 0.025 Uiso 1 1 calc R
C9 C 0.8052(2) 0.30154(9) -0.2049(2) 0.0195(5) Uani 1 1 d .
H9 H 0.8591 0.3324 -0.1757 0.023 Uiso 1 1 calc R
C10 C 0.7036(2) 0.12483(9) -0.0592(2) 0.0192(5) Uani 1 1 d .
C11 C 0.8147(2) 0.12231(9) 0.0425(2) 0.0187(5) Uani 1 1 d .
C12 C 0.9061(2) 0.07891(10) 0.0700(2) 0.0237(5) Uani 1 1 d .
H12 H 0.9062 0.0462 0.0199 0.028 Uiso 1 1 calc R
C13 C 0.9963(2) 0.08587(10) 0.1736(2) 0.0252(5) Uani 1 1 d .
C14 C 0.9961(2) 0.13326(10) 0.2497(2) 0.0231(5) Uani 1 1 d .
H14 H 1.0583 0.1359 0.3218 0.028 Uiso 1 1 calc R
C15 C 0.9056(2) 0.17641(10) 0.2205(2) 0.0200(5) Uani 1 1 d .
H15 H 0.9059 0.2090 0.2710 0.024 Uiso 1 1 calc R
C16 C 0.8142(2) 0.17070(9) 0.1151(2) 0.0162(5) Uani 1 1 d .
C17 C 0.7364(2) 0.33631(9) 0.1745(2) 0.0176(5) Uani 1 1 d .
C18 C 0.6456(3) 0.38423(10) 0.2115(2) 0.0230(5) Uani 1 1 d .
C19 C 0.5003(3) 0.36186(11) 0.2196(3) 0.0366(7) Uani 1 1 d .
H19A H 0.4647 0.3488 0.1366 0.055 Uiso 1 1 calc R
H19B H 0.4418 0.3917 0.2478 0.055 Uiso 1 1 calc R
H19C H 0.5017 0.3309 0.2794 0.055 Uiso 1 1 calc R
C20 C 0.6492(3) 0.43046(11) 0.1135(3) 0.0386(7) Uani 1 1 d .
H20A H 0.7437 0.4421 0.1059 0.058 Uiso 1 1 calc R
H20B H 0.5958 0.4624 0.1393 0.058 Uiso 1 1 calc R
H20C H 0.6104 0.4166 0.0323 0.058 Uiso 1 1 calc R
C21 C 0.6993(3) 0.40644(12) 0.3410(3) 0.0434(8) Uani 1 1 d .
H21A H 0.6937 0.3769 0.4039 0.065 Uiso 1 1 calc R
H21B H 0.6440 0.4383 0.3637 0.065 Uiso 1 1 calc R
H21C H 0.7943 0.4182 0.3379 0.065 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'
Br Br -0.2901 2.4595 '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 109.5
C2 O2 H2 109.5
C17 O3 C3 116.16(17)
O1 C1 C5 115.82(18)
O1 C1 C10 111.13(18)
C5 C1 C10 109.77(18)
O1 C1 C2 109.13(17)
C5 C1 C2 104.71(18)
C10 C1 C2 105.60(18)
O2 C2 C16 109.73(17)
O2 C2 C1 113.74(17)
C16 C2 C1 103.94(18)
O2 C2 C3 111.85(18)
C16 C2 C3 111.43(18)
C1 C2 C3 105.86(17)
O3 C3 C4 108.32(17)
O3 C3 C2 110.59(18)
C4 C3 C2 104.58(17)
O3 C3 H3 111.0
C4 C3 H3 111.0
C2 C3 H3 111.0
C5 C4 C9 120.5(2)
C5 C4 C3 112.64(19)
C9 C4 C3 126.8(2)
C4 C5 C6 121.4(2)
C4 C5 C1 111.70(19)
C6 C5 C1 126.9(2)
C7 C6 C5 116.9(2)
C7 C6 H6 121.5
C5 C6 H6 121.5
C6 C7 C8 122.6(2)
C6 C7 Br1 118.93(17)
C8 C7 Br1 118.44(17)
C9 C8 C7 119.0(2)
C9 C8 H8 120.5
C7 C8 H8 120.5
C8 C9 C4 119.6(2)
C8 C9 H9 120.2
C4 C9 H9 120.2
O4 C10 C11 127.4(2)
O4 C10 C1 125.1(2)
C11 C10 C1 107.52(18)
C12 C11 C16 122.2(2)
C12 C11 C10 127.9(2)
C16 C11 C10 109.9(2)
C13 C12 C11 116.6(2)
C13 C12 H12 121.7
C11 C12 H12 121.7
C12 C13 C14 122.5(2)
C12 C13 Br2 118.41(19)
C14 C13 Br2 119.05(19)
C15 C14 C13 120.3(2)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C16 118.3(2)
C14 C15 H15 120.9
C16 C15 H15 120.9
C15 C16 C11 120.1(2)
C15 C16 C2 127.2(2)
C11 C16 C2 112.67(19)
O5 C17 O3 121.8(2)
O5 C17 C18 126.1(2)
O3 C17 C18 112.14(19)
C17 C18 C20 108.9(2)
C17 C18 C19 108.5(2)
C20 C18 C19 111.2(2)
C17 C18 C21 109.0(2)
C20 C18 C21 110.0(2)
C19 C18 C21 109.2(2)
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C18 C20 H20A 109.5
C18 C20 H20B 109.5
H20A C20 H20B 109.5
C18 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C18 C21 H21A 109.5
C18 C21 H21B 109.5
H21A C21 H21B 109.5
C18 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C7 1.909(2)
Br2 C13 1.909(3)
O1 C1 1.421(3)
O1 H1 0.8400
O2 C2 1.413(3)
O2 H2 0.8400
O3 C17 1.346(3)
O3 C3 1.448(3)
O4 C10 1.210(3)
O5 C17 1.211(3)
C1 C5 1.511(3)
C1 C10 1.544(4)
C1 C2 1.576(3)
C2 C16 1.513(3)
C2 C3 1.583(3)
C3 C4 1.497(3)
C3 H3 1.0000
C4 C5 1.385(3)
C4 C9 1.394(3)
C5 C6 1.396(3)
C6 C7 1.392(3)
C6 H6 0.9500
C7 C8 1.400(3)
C8 C9 1.381(3)
C8 H8 0.9500
C9 H9 0.9500
C10 C11 1.484(3)
C11 C12 1.393(3)
C11 C16 1.397(3)
C12 C13 1.377(3)
C12 H12 0.9500
C13 C14 1.397(4)
C14 C15 1.385(3)
C14 H14 0.9500
C15 C16 1.394(3)
C15 H15 0.9500
C17 C18 1.526(3)
C18 C20 1.528(4)
C18 C19 1.536(4)
C18 C21 1.539(3)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
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 5.0(2)
C5 C1 C2 O2 129.58(19)
C10 C1 C2 O2 -114.5(2)
O1 C1 C2 C16 124.28(18)
C5 C1 C2 C16 -111.13(19)
C10 C1 C2 C16 4.7(2)
O1 C1 C2 C3 -118.21(19)
C5 C1 C2 C3 6.4(2)
C10 C1 C2 C3 122.25(19)
C17 O3 C3 C4 -158.31(18)
C17 O3 C3 C2 87.6(2)
O2 C2 C3 O3 -15.1(2)
C16 C2 C3 O3 -138.33(17)
C1 C2 C3 O3 109.30(18)
O2 C2 C3 C4 -131.49(18)
C16 C2 C3 C4 105.27(19)
C1 C2 C3 C4 -7.1(2)
O3 C3 C4 C5 -112.5(2)
C2 C3 C4 C5 5.4(2)
O3 C3 C4 C9 67.6(3)
C2 C3 C4 C9 -174.5(2)
C9 C4 C5 C6 -0.4(3)
C3 C4 C5 C6 179.74(19)
C9 C4 C5 C1 178.53(19)
C3 C4 C5 C1 -1.4(3)
O1 C1 C5 C4 116.9(2)
C10 C1 C5 C4 -116.3(2)
C2 C1 C5 C4 -3.3(2)
O1 C1 C5 C6 -64.3(3)
C10 C1 C5 C6 62.5(3)
C2 C1 C5 C6 175.5(2)
C4 C5 C6 C7 -0.8(3)
C1 C5 C6 C7 -179.5(2)
C5 C6 C7 C8 0.6(3)
C5 C6 C7 Br1 -179.14(16)
C6 C7 C8 C9 0.7(3)
Br1 C7 C8 C9 -179.53(17)
C7 C8 C9 C4 -1.9(3)
C5 C4 C9 C8 1.7(3)
C3 C4 C9 C8 -178.4(2)
O1 C1 C10 O4 55.5(3)
C5 C1 C10 O4 -73.9(3)
C2 C1 C10 O4 173.7(2)
O1 C1 C10 C11 -124.31(18)
C5 C1 C10 C11 106.3(2)
C2 C1 C10 C11 -6.1(2)
O4 C10 C11 C12 3.2(4)
C1 C10 C11 C12 -177.0(2)
O4 C10 C11 C16 -174.6(2)
C1 C10 C11 C16 5.2(2)
C16 C11 C12 C13 0.4(3)
C10 C11 C12 C13 -177.1(2)
C11 C12 C13 C14 1.1(4)
C11 C12 C13 Br2 -177.71(17)
C12 C13 C14 C15 -1.9(4)
Br2 C13 C14 C15 176.95(17)
C13 C14 C15 C16 1.0(3)
C14 C15 C16 C11 0.4(3)
C14 C15 C16 C2 179.1(2)
C12 C11 C16 C15 -1.2(3)
C10 C11 C16 C15 176.71(19)
C12 C11 C16 C2 180.0(2)
C10 C11 C16 C2 -2.1(3)
O2 C2 C16 C15 -58.5(3)
C1 C2 C16 C15 179.5(2)
C3 C2 C16 C15 65.9(3)
O2 C2 C16 C11 120.2(2)
C1 C2 C16 C11 -1.8(2)
C3 C2 C16 C11 -115.3(2)
C3 O3 C17 O5 4.2(3)
C3 O3 C17 C18 -176.11(17)
O5 C17 C18 C20 121.2(3)
O3 C17 C18 C20 -58.5(3)
O5 C17 C18 C19 -117.7(3)
O3 C17 C18 C19 62.7(2)
O5 C17 C18 C21 1.2(3)
O3 C17 C18 C21 -178.5(2)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 -0.021 329 106 ' '
2 0.500 1.000 0.539 329 106 ' '
