#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/28/1502834.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_1502834
loop_
_publ_author_name
'Xu, Liangxiong'
'He, Zhengxiang'
'Xue, Jinghua'
'Chen, Xiaoping'
'Wei, Xiaoyi'
_publ_section_title
;
 beta-Resorcylic acid lactones from a Paecilomyces fungus.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              885
_journal_page_last               889
_journal_paper_doi               10.1021/np900853n
_journal_volume                  73
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H24 O8'
_chemical_formula_sum            'C19 H24 O8'
_chemical_formula_weight         380.38
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7386(3)
_cell_length_b                   9.6557(5)
_cell_length_c                   27.6093(13)
_cell_measurement_reflns_used    5694
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.23
_cell_volume                     1796.42(15)
_computing_cell_refinement       'SAINT-PLUS (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT-PLUS
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2005)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker AXS SMART 1000 CCD diffractometer'
_diffrn_measurement_method       'ω 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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9192
_diffrn_reflns_theta_full        27.01
_diffrn_reflns_theta_max         27.01
_diffrn_reflns_theta_min         1.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9762
_exptl_absorpt_correction_T_min  0.9481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         2264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0346
_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)+(0.0606P)²+0.4061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                2093
_reflns_number_total             2264
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np900853n_si_002.cif
_cod_data_source_block           01101m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1502834
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
C1 C 1.1175(3) 0.9320(2) 0.03115(7) 0.0182(4) Uani 1 1 d .
C2 C 1.1248(3) 0.9355(2) -0.02065(7) 0.0192(4) Uani 1 1 d .
C3 C 1.1334(3) 1.0594(2) -0.04568(7) 0.0199(4) Uani 1 1 d .
H3 H 1.1371 1.0593 -0.0801 0.024 Uiso 1 1 calc R
C4 C 1.1365(3) 1.1835(2) -0.02069(7) 0.0187(4) Uani 1 1 d .
C5 C 1.1367(3) 1.1844(2) 0.03002(7) 0.0180(4) Uani 1 1 d .
H5 H 1.1459 1.2698 0.0470 0.022 Uiso 1 1 calc R
C6 C 1.1235(3) 1.0609(2) 0.05574(7) 0.0177(4) Uani 1 1 d .
C7 C 1.0973(3) 0.7935(2) 0.05339(7) 0.0202(4) Uani 1 1 d .
C8 C 1.1323(3) 1.4309(2) -0.02438(7) 0.0225(4) Uani 1 1 d .
H8A H 1.2523 1.4426 -0.0047 0.034 Uiso 1 1 calc R
H8B H 1.0151 1.4349 -0.0034 0.034 Uiso 1 1 calc R
H8C H 1.1251 1.5050 -0.0486 0.034 Uiso 1 1 calc R
C9 C 1.2274(4) 0.5682(2) 0.12603(9) 0.0294(5) Uani 1 1 d .
H9A H 1.3234 0.6202 0.1455 0.044 Uiso 1 1 calc R
H9B H 1.2818 0.5528 0.0935 0.044 Uiso 1 1 calc R
H9C H 1.2008 0.4787 0.1415 0.044 Uiso 1 1 calc R
C1' C 1.1075(3) 1.0754(2) 0.10979(6) 0.0185(4) Uani 1 1 d .
H1' H 1.1197 0.9881 0.1290 0.022 Uiso 1 1 calc R
C2' C 0.9839(3) 1.1862(2) 0.13128(7) 0.0191(4) Uani 1 1 d .
H2' H 0.9127 1.2462 0.1074 0.023 Uiso 1 1 calc R
C3' C 0.8804(3) 1.1679(2) 0.17920(7) 0.0212(4) Uani 1 1 d .
H3'1 H 0.9119 1.2467 0.2008 0.025 Uiso 1 1 calc R
H3'2 H 0.9267 1.0817 0.1950 0.025 Uiso 1 1 calc R
C4' C 0.6568(3) 1.1605(2) 0.17074(7) 0.0198(4) Uani 1 1 d .
H4' H 0.6327 1.1113 0.1394 0.024 Uiso 1 1 calc R
C5' C 0.5392(3) 1.0860(2) 0.21068(7) 0.0207(4) Uani 1 1 d .
H5' H 0.4051 1.1301 0.2127 0.025 Uiso 1 1 calc R
C6' C 0.5098(3) 0.9322(2) 0.20018(7) 0.0220(4) Uani 1 1 d .
H6' H 0.4541 0.9234 0.1668 0.026 Uiso 1 1 calc R
C7' C 0.6992(3) 0.8504(2) 0.20208(7) 0.0235(4) Uani 1 1 d .
H7' H 0.7834 0.8627 0.2293 0.028 Uiso 1 1 calc R
C8' C 0.7555(3) 0.7630(2) 0.16840(7) 0.0245(5) Uani 1 1 d .
H8' H 0.6739 0.7537 0.1405 0.029 Uiso 1 1 calc R
C9' C 0.9404(4) 0.6765(2) 0.17105(7) 0.0269(5) Uani 1 1 d .
H9'1 H 0.9073 0.5865 0.1862 0.032 Uiso 1 1 calc R
H9'2 H 1.0376 0.7237 0.1923 0.032 Uiso 1 1 calc R
C10' C 1.0365(4) 0.6497(2) 0.12224(7) 0.0225(4) Uani 1 1 d .
H10' H 0.9411 0.5985 0.1010 0.027 Uiso 1 1 calc R
O1 O 1.1198(3) 0.81991(16) -0.04799(5) 0.0251(3) Uani 1 1 d .
H1 H 1.1107 0.7502 -0.0299 0.038 Uiso 1 1 calc R
O2 O 1.1388(2) 1.29919(15) -0.04842(5) 0.0227(3) Uani 1 1 d .
O3 O 1.1970(2) 1.19847(16) 0.13082(5) 0.0217(3) Uani 1 1 d .
O4 O 0.5906(2) 1.30153(15) 0.16560(5) 0.0257(3) Uani 1 1 d .
H4 H 0.4738 1.3023 0.1550 0.038 Uiso 1 1 calc R
O5 O 0.6283(3) 1.09397(16) 0.25729(5) 0.0248(3) Uani 1 1 d .
H5A H 0.6361 1.1773 0.2659 0.037 Uiso 1 1 calc R
O6 O 0.3653(2) 0.87838(16) 0.23359(5) 0.0270(4) Uani 1 1 d .
H6 H 0.4019 0.8948 0.2621 0.041 Uiso 1 1 calc R
O7 O 1.0754(2) 0.78859(14) 0.10121(5) 0.0228(3) Uani 1 1 d .
O8 O 1.0964(3) 0.68719(16) 0.02913(5) 0.0286(4) Uani 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 0.0000 '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 0.0000 '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
C6 C1 C2 117.17(18)
C6 C1 C7 126.72(16)
C2 C1 C7 116.08(17)
O1 C2 C3 115.95(17)
O1 C2 C1 122.62(18)
C3 C2 C1 121.42(18)
C2 C3 C4 120.05(17)
C2 C3 H3 120.0
C4 C3 H3 120.0
O2 C4 C3 115.64(16)
O2 C4 C5 124.06(17)
C3 C4 C5 120.30(18)
C6 C5 C4 120.33(18)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C1 120.66(16)
C5 C6 C1' 115.59(17)
C1 C6 C1' 123.70(18)
O8 C7 O7 120.85(18)
O8 C7 C1 122.08(17)
O7 C7 C1 117.05(16)
O2 C8 H8A 109.5
O2 C8 H8B 109.5
H8A C8 H8B 109.5
O2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10' C9 H9A 109.5
C10' C9 H9B 109.5
H9A C9 H9B 109.5
C10' C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O3 C1' C2' 58.85(12)
O3 C1' C6 116.29(16)
C2' C1' C6 120.38(17)
O3 C1' H1' 116.3
C2' C1' H1' 116.3
C6 C1' H1' 116.3
O3 C2' C1' 59.67(13)
O3 C2' C3' 118.61(17)
C1' C2' C3' 121.88(18)
O3 C2' H2' 115.1
C1' C2' H2' 115.1
C3' C2' H2' 115.1
C2' C3' C4' 109.16(16)
C2' C3' H3'1 109.8
C4' C3' H3'1 109.8
C2' C3' H3'2 109.8
C4' C3' H3'2 109.8
H3'1 C3' H3'2 108.3
O4 C4' C3' 106.08(18)
O4 C4' C5' 110.71(17)
C3' C4' C5' 114.90(17)
O4 C4' H4' 108.3
C3' C4' H4' 108.3
C5' C4' H4' 108.3
O5 C5' C6' 106.21(16)
O5 C5' C4' 113.99(17)
C6' C5' C4' 112.71(16)
O5 C5' H5' 107.9
C6' C5' H5' 107.9
C4' C5' H5' 107.9
O6 C6' C7' 111.29(17)
O6 C6' C5' 108.51(16)
C7' C6' C5' 113.27(18)
O6 C6' H6' 107.9
C7' C6' H6' 107.9
C5' C6' H6' 107.9
C8' C7' C6' 124.0(2)
C8' C7' H7' 118.0
C6' C7' H7' 118.0
C7' C8' C9' 124.3(2)
C7' C8' H8' 117.9
C9' C8' H8' 117.9
C8' C9' C10' 113.93(18)
C8' C9' H9'1 108.8
C10' C9' H9'1 108.8
C8' C9' H9'2 108.8
C10' C9' H9'2 108.8
H9'1 C9' H9'2 107.7
O7 C10' C9 110.31(18)
O7 C10' C9' 105.56(16)
C9 C10' C9' 112.98(18)
O7 C10' H10' 109.3
C9 C10' H10' 109.3
C9' C10' H10' 109.3
C2 O1 H1 109.5
C4 O2 C8 117.98(14)
C2' O3 C1' 61.48(13)
C4' O4 H4 109.5
C5' O5 H5A 109.5
C6' O6 H6 109.5
C7 O7 C10' 116.09(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.418(3)
C1 C2 1.431(3)
C1 C7 1.479(3)
C2 O1 1.348(2)
C2 C3 1.383(3)
C3 C4 1.383(3)
C3 H3 0.9500
C4 O2 1.354(2)
C4 C5 1.400(3)
C5 C6 1.391(3)
C5 H5 0.9500
C6 C1' 1.503(2)
C7 O8 1.225(2)
C7 O7 1.329(2)
C8 O2 1.435(2)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10' 1.512(3)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C1' O3 1.454(2)
C1' C2' 1.480(3)
C1' H1' 1.0000
C2' O3 1.441(3)
C2' C3' 1.506(3)
C2' H2' 1.0000
C3' C4' 1.526(3)
C3' H3'1 0.9900
C3' H3'2 0.9900
C4' O4 1.440(3)
C4' C5' 1.537(3)
C4' H4' 1.0000
C5' O5 1.422(2)
C5' C6' 1.527(3)
C5' H5' 1.0000
C6' O6 1.439(3)
C6' C7' 1.502(3)
C6' H6' 1.0000
C7' C8' 1.312(3)
C7' H7' 0.9500
C8' C9' 1.502(3)
C8' H8' 0.9500
C9' C10' 1.517(3)
C9' H9'1 0.9900
C9' H9'2 0.9900
C10' O7 1.485(2)
C10' H10' 1.0000
O1 H1 0.8400
O4 H4 0.8400
O5 H5A 0.8400
O6 H6 0.8400
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 O8 0.84 1.74 2.490(2) 147.0 .
O4 H4 O3 0.84 2.22 2.991(2) 152.6 1_455
O5 H5A O6 0.84 1.94 2.758(2) 163.6 3_655
O6 H6 O4 0.84 2.19 2.896(2) 141.5 3_645
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
C6 C1 C2 O1 -179.91(18)
C7 C1 C2 O1 -2.0(3)
C6 C1 C2 C3 -1.2(3)
C7 C1 C2 C3 176.69(19)
O1 C2 C3 C4 179.2(2)
C1 C2 C3 C4 0.5(3)
C2 C3 C4 O2 -178.0(2)
C2 C3 C4 C5 1.8(3)
O2 C4 C5 C6 176.54(19)
C3 C4 C5 C6 -3.3(3)
C4 C5 C6 C1 2.5(3)
C4 C5 C6 C1' -174.98(19)
C2 C1 C6 C5 -0.2(3)
C7 C1 C6 C5 -177.9(2)
C2 C1 C6 C1' 177.0(2)
C7 C1 C6 C1' -0.7(3)
C6 C1 C7 O8 -178.9(2)
C2 C1 C7 O8 3.4(3)
C6 C1 C7 O7 2.6(3)
C2 C1 C7 O7 -175.12(19)
C5 C6 C1' O3 -27.9(3)
C1 C6 C1' O3 154.77(18)
C5 C6 C1' C2' 39.8(3)
C1 C6 C1' C2' -137.5(2)
C6 C1' C2' O3 -104.2(2)
O3 C1' C2' C3' -106.8(2)
C6 C1' C2' C3' 148.96(19)
O3 C2' C3' C4' 178.76(18)
C1' C2' C3' C4' -111.0(2)
C2' C3' C4' O4 -80.8(2)
C2' C3' C4' C5' 156.53(17)
O4 C4' C5' O5 -91.7(2)
C3' C4' C5' O5 28.4(3)
O4 C4' C5' C6' 147.15(17)
C3' C4' C5' C6' -92.7(2)
O5 C5' C6' O6 66.5(2)
C4' C5' C6' O6 -168.04(16)
O5 C5' C6' C7' -57.6(2)
C4' C5' C6' C7' 67.9(2)
O6 C6' C7' C8' 106.1(2)
C5' C6' C7' C8' -131.3(2)
C6' C7' C8' C9' -177.4(2)
C7' C8' C9' C10' -147.1(2)
C8' C9' C10' O7 56.7(2)
C8' C9' C10' C9 177.31(19)
C3 C4 O2 C8 177.0(2)
C5 C4 O2 C8 -2.8(3)
C3' C2' O3 C1' 112.2(2)
C6 C1' O3 C2' 111.1(2)
O8 C7 O7 C10' -4.0(3)
C1 C7 O7 C10' 174.47(17)
C9 C10' O7 C7 79.0(2)
C9' C10' O7 C7 -158.59(19)
