#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:46:30 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178915 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/44/4114412.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_4114412
loop_
_publ_author_name
'Wei He'
'Xiufeng Sun'
'Alison J. Frontier'
_publ_section_title
;
 Polarizing the Nazarov Cyclization: Efficient Catalysis under Mild
 Conditions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14278
_journal_page_last               14279
_journal_paper_doi               10.1021/ja037910b
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C19 H22 O7'
_chemical_formula_weight         362.37
_chemical_name_common            frowh02
_chemical_name_systematic
;
 4a
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 109.88(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1639(19)
_cell_length_b                   12.296(2)
_cell_length_c                   14.944(3)
_cell_measurement_reflns_used    6471
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     1756.3(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13812
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0400
_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)+(0.0519P)²+0.5186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                2922
_reflns_number_total             3582
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja037910bsi20030814_043516_2.cif
_cod_data_source_block           frowh02
_cod_original_cell_volume        1756.4(6)
_cod_database_code               4114412
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
C1 C 0.73031(14) 0.23672(12) 0.57392(10) 0.0256(3) Uani 1 1 d
C2 C 0.88981(15) 0.23457(12) 0.61534(11) 0.0287(3) Uani 1 1 d
C3 C 0.92528(14) 0.20483(12) 0.71530(10) 0.0274(3) Uani 1 1 d
C5 C 1.07635(17) 0.15942(15) 0.86847(12) 0.0387(4) Uani 1 1 d
C6 C 0.95634(18) 0.09480(14) 0.87898(12) 0.0380(4) Uani 1 1 d
C7 C 0.81993(16) 0.15723(14) 0.83657(11) 0.0313(3) Uani 1 1 d
C8 C 0.81198(14) 0.19714(11) 0.74093(10) 0.0255(3) Uani 1 1 d
C9 C 0.67987(14) 0.22871(11) 0.66147(10) 0.0243(3) Uani 1 1 d
C11 C 0.67104(15) 0.33509(12) 0.51451(10) 0.0275(3) Uani 1 1 d
C12 C 0.4750(2) 0.39931(17) 0.38747(14) 0.0443(4) Uani 1 1 d
C13 C 0.55639(14) 0.15358(11) 0.64803(9) 0.0239(3) Uani 1 1 d
C14 C 0.42607(14) 0.19340(11) 0.64467(10) 0.0259(3) Uani 1 1 d
C15 C 0.31216(15) 0.12493(12) 0.63440(11) 0.0288(3) Uani 1 1 d
C16 C 0.33073(15) 0.01411(12) 0.62742(11) 0.0305(3) Uani 1 1 d
C17 C 0.45744(15) -0.02925(12) 0.62849(11) 0.0296(3) Uani 1 1 d
C18 C 0.56776(14) 0.04077(12) 0.63825(10) 0.0261(3) Uani 1 1 d
C19 C 0.28423(18) 0.35123(15) 0.63347(16) 0.0431(4) Uani 1 1 d
C20 C 0.1053(3) -0.0269(2) 0.6339(3) 0.0789(9) Uani 1 1 d
C21 C 0.7093(2) -0.10350(14) 0.61384(15) 0.0410(4) Uani 1 1 d
O1 O 0.96919(11) 0.24880(10) 0.57130(8) 0.0432(3) Uani 1 1 d
O2 O 0.71990(12) 0.42492(9) 0.52832(9) 0.0426(3) Uani 1 1 d
O3 O 0.55143(11) 0.31040(9) 0.44515(7) 0.0357(3) Uani 1 1 d
O4 O 1.06042(10) 0.18363(9) 0.76988(8) 0.0352(3) Uani 1 1 d
O5 O 0.41785(10) 0.30370(8) 0.65289(9) 0.0396(3) Uani 1 1 d
O6 O 0.22777(12) -0.06155(9) 0.61744(10) 0.0479(3) Uani 1 1 d
O7 O 0.69657(10) 0.00615(8) 0.64029(8) 0.0336(3) Uani 1 1 d
H1 H 0.7025(15) 0.1722(13) 0.5372(11) 0.022(4) Uiso 1 1 d
H5A H 1.1633(19) 0.1179(15) 0.8910(13) 0.041(5) Uiso 1 1 d
H5B H 1.0848(19) 0.2314(16) 0.9049(13) 0.048(5) Uiso 1 1 d
H6A H 0.9766(18) 0.0811(14) 0.9485(13) 0.040(5) Uiso 1 1 d
H6B H 0.9527(18) 0.0233(16) 0.8455(12) 0.041(5) Uiso 1 1 d
H7A H 0.7373(18) 0.1093(14) 0.8290(11) 0.034(4) Uiso 1 1 d
H7B H 0.8141(17) 0.2154(15) 0.8758(12) 0.036(5) Uiso 1 1 d
H9 H 0.6504(16) 0.3007(13) 0.6757(11) 0.026(4) Uiso 1 1 d
H12A H 0.444(3) 0.448(2) 0.4219(18) 0.079(8) Uiso 1 1 d
H12B H 0.522(3) 0.4297(19) 0.3488(18) 0.077(7) Uiso 1 1 d
H12C H 0.385(3) 0.366(2) 0.3418(18) 0.082(8) Uiso 1 1 d
H15 H 0.2259(18) 0.1527(14) 0.6329(11) 0.034(4) Uiso 1 1 d
H17 H 0.4657(17) -0.1058(15) 0.6237(12) 0.036(4) Uiso 1 1 d
H19A H 0.296(2) 0.425(2) 0.6381(17) 0.077(7) Uiso 1 1 d
H19B H 0.239(2) 0.3223(18) 0.6823(16) 0.070(7) Uiso 1 1 d
H19C H 0.220(3) 0.3295(19) 0.5730(18) 0.077(7) Uiso 1 1 d
H20A H 0.057(2) 0.023(2) 0.5881(16) 0.063(7) Uiso 1 1 d
H20B H 0.048(3) -0.091(2) 0.6256(19) 0.093(8) Uiso 1 1 d
H21A H 0.804(2) -0.1107(17) 0.6136(15) 0.060(6) Uiso 1 1 d
H21B H 0.701(2) -0.1529(18) 0.6620(15) 0.053(6) Uiso 1 1 d
H21C H 0.641(2) -0.1213(17) 0.5521(15) 0.055(6) Uiso 1 1 d
H20C H 0.121(3) 0.013(3) 0.692(2) 0.115(12) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 C1 C2 114.29(12)
C11 C1 C9 111.49(11)
C2 C1 C9 105.37(11)
O1 C2 C3 127.76(14)
O1 C2 C1 125.96(14)
C3 C2 C1 106.15(12)
C8 C3 O4 127.37(13)
C8 C3 C2 112.00(13)
O4 C3 C2 120.55(12)
O4 C5 C6 113.41(13)
C5 C6 C7 110.21(14)
C8 C7 C6 108.11(13)
C3 C8 C7 121.93(13)
C3 C8 C9 112.30(13)
C7 C8 C9 125.72(12)
C8 C9 C13 114.98(11)
C8 C9 C1 102.56(11)
C13 C9 C1 114.84(11)
O2 C11 O3 123.81(14)
O2 C11 C1 125.53(13)
O3 C11 C1 110.60(12)
C14 C13 C18 116.95(12)
C14 C13 C9 121.56(12)
C18 C13 C9 121.49(12)
O5 C14 C13 115.52(12)
O5 C14 C15 122.28(13)
C13 C14 C15 122.20(13)
C16 C15 C14 118.19(13)
O6 C16 C15 123.92(13)
O6 C16 C17 114.30(13)
C15 C16 C17 121.78(13)
C18 C17 C16 118.55(13)
O7 C18 C17 123.02(13)
O7 C18 C13 114.68(12)
C17 C18 C13 122.30(13)
C11 O3 C12 116.97(13)
C3 O4 C5 112.76(11)
C14 O5 C19 118.37(12)
C16 O6 C20 117.47(14)
C18 O7 C21 117.77(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C11 1.500(2)
C1 C2 1.526(2)
C1 C9 1.5623(19)
C2 O1 1.2148(18)
C2 C3 1.459(2)
C3 C8 1.335(2)
C3 O4 1.3630(17)
C5 O4 1.457(2)
C5 C6 1.508(2)
C6 C7 1.522(2)
C7 C8 1.487(2)
C8 C9 1.510(2)
C9 C13 1.5157(19)
C11 O2 1.1998(18)
C11 O3 1.3370(18)
C12 O3 1.445(2)
C13 C14 1.3970(19)
C13 C18 1.404(2)
C14 O5 1.3670(17)
C14 C15 1.397(2)
C15 C16 1.384(2)
C16 O6 1.3700(17)
C16 C17 1.389(2)
C17 C18 1.382(2)
C18 O7 1.3672(16)
C19 O5 1.4150(19)
C20 O6 1.414(2)
C21 O7 1.4234(19)
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
C11 C1 C2 O1 -50.3(2)
C9 C1 C2 O1 -173.04(15)
C11 C1 C2 C3 133.55(13)
C9 C1 C2 C3 10.81(15)
O1 C2 C3 C8 179.24(15)
C1 C2 C3 C8 -4.70(16)
O1 C2 C3 O4 -3.7(2)
C1 C2 C3 O4 172.38(12)
O4 C5 C6 C7 -59.8(2)
C5 C6 C7 C8 47.74(18)
O4 C3 C8 C7 -3.0(2)
C2 C3 C8 C7 173.81(13)
O4 C3 C8 C9 179.26(13)
C2 C3 C8 C9 -3.90(17)
C6 C7 C8 C3 -19.2(2)
C6 C7 C8 C9 158.21(13)
C3 C8 C9 C13 135.79(13)
C7 C8 C9 C13 -41.82(19)
C3 C8 C9 C1 10.43(15)
C7 C8 C9 C1 -167.18(14)
C11 C1 C9 C8 -136.97(12)
C2 C1 C9 C8 -12.45(14)
C11 C1 C9 C13 97.58(14)
C2 C1 C9 C13 -137.90(12)
C2 C1 C11 O2 -34.2(2)
C9 C1 C11 O2 85.12(18)
C2 C1 C11 O3 148.33(12)
C9 C1 C11 O3 -92.32(14)
C8 C9 C13 C14 128.06(14)
C1 C9 C13 C14 -113.25(15)
C8 C9 C13 C18 -52.02(18)
C1 C9 C13 C18 66.67(17)
C18 C13 C14 O5 -179.00(12)
C9 C13 C14 O5 0.92(19)
C18 C13 C14 C15 1.5(2)
C9 C13 C14 C15 -178.57(13)
O5 C14 C15 C16 -179.44(14)
C13 C14 C15 C16 0.0(2)
C14 C15 C16 O6 179.80(14)
C14 C15 C16 C17 -1.3(2)
O6 C16 C17 C18 179.99(13)
C15 C16 C17 C18 1.0(2)
C16 C17 C18 O7 179.87(13)
C16 C17 C18 C13 0.6(2)
C14 C13 C18 O7 178.87(12)
C9 C13 C18 O7 -1.05(19)
C14 C13 C18 C17 -1.8(2)
C9 C13 C18 C17 178.23(13)
O2 C11 O3 C12 -3.2(2)
C1 C11 O3 C12 174.28(13)
C8 C3 O4 C5 -5.6(2)
C2 C3 O4 C5 177.82(13)
C6 C5 O4 C3 36.88(19)
C13 C14 O5 C19 169.06(15)
C15 C14 O5 C19 -11.5(2)
C15 C16 O6 C20 -12.9(3)
C17 C16 O6 C20 168.2(2)
C17 C18 O7 C21 11.8(2)
C13 C18 O7 C21 -168.91(14)
