# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_lchb9_0m
_database_code_depnum_ccdc_archive 'CCDC 1963364'
loop_
_audit_author_name
_audit_author_address
'Xiao-Nian Li'
;Kunming Institute of Botany, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2020-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Xylarilongipin A'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H28 O2, H2 O'
_chemical_formula_sum            'C19 H30 O3'
_chemical_formula_weight         306.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.5487(2)
_cell_length_b                   6.7333(2)
_cell_length_c                   15.8235(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.4590(10)
_cell_angle_gamma                90
_cell_volume                     802.81(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5686
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      70.40

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   0.6176
_exptl_transmission_factor_max   0.7533
_exptl_crystal_size_max          0.980
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.658
_shelx_estimated_absorpt_T_min   0.565
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6294
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.798
_diffrn_reflns_theta_max         70.341
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.740
_diffrn_reflns_point_group_measured_fraction_full 0.769
_reflns_number_total             2275
_reflns_number_gt                2240
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.470
_reflns_Friedel_fraction_max     0.520
_reflns_Friedel_fraction_full    0.549

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0625P)²+0.1668P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 701 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2275
_refine_ls_number_parameters     202
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1S O 0.16315(19) 0.2180(3) 0.50416(10) 0.0225(4) Uani 1 1 d . . . . .
H1SA H 0.1531 0.3215 0.4658 0.034 Uiso 1 1 d R U . . .
H1SB H 0.2712 0.2110 0.5193 0.034 Uiso 1 1 d R U . . .
O4 O 0.91900(17) 0.0449(3) 0.60517(9) 0.0185(4) Uani 1 1 d . . . . .
H4 H 0.9981 0.0880 0.5749 0.028 Uiso 1 1 calc R U . . .
O6 O 0.52144(18) 0.1403(3) 0.55561(9) 0.0169(4) Uani 1 1 d . . . . .
C17 C 0.1125(3) -0.1874(5) 0.94014(14) 0.0237(6) Uani 1 1 d . . . . .
H17A H 0.1350 -0.1618 1.0008 0.036 Uiso 1 1 calc R U . . .
H17B H 0.1309 -0.3287 0.9287 0.036 Uiso 1 1 calc R U . . .
H17C H -0.0102 -0.1510 0.9229 0.036 Uiso 1 1 calc R U . . .
C13 C 0.2398(3) -0.0636(4) 0.89023(13) 0.0179(5) Uani 1 1 d . . . . .
C14 C 0.1961(3) -0.0831(4) 0.79426(13) 0.0166(5) Uani 1 1 d . . . . .
H14A H 0.1810 -0.2248 0.7788 0.020 Uiso 1 1 calc R U . . .
H14B H 0.0837 -0.0129 0.7784 0.020 Uiso 1 1 calc R U . . .
C8 C 0.3459(2) 0.0062(4) 0.74729(14) 0.0145(5) Uani 1 1 d . . . . .
C9 C 0.4619(3) 0.1476(4) 0.80178(13) 0.0139(5) Uani 1 1 d . . . . .
C10 C 0.5815(3) 0.2704(4) 0.74454(13) 0.0149(5) Uani 1 1 d . . . . .
C5 C 0.6754(3) 0.1189(4) 0.68827(13) 0.0138(5) Uani 1 1 d . . . . .
H5 H 0.7403 0.0200 0.7258 0.017 Uiso 1 1 calc R U . . .
C4 C 0.8050(3) 0.2067(4) 0.62757(13) 0.0162(5) Uani 1 1 d . . . . .
C3 C 0.9223(3) 0.3739(4) 0.66601(14) 0.0190(5) Uani 1 1 d . . . . .
H3A H 1.0311 0.3134 0.6929 0.023 Uiso 1 1 calc R U . . .
H3B H 0.9589 0.4596 0.6193 0.023 Uiso 1 1 calc R U . . .
C2 C 0.8387(3) 0.5064(4) 0.73174(15) 0.0225(6) Uani 1 1 d . . . . .
H2A H 0.7605 0.6053 0.7020 0.027 Uiso 1 1 calc R U . . .
H2B H 0.9339 0.5794 0.7644 0.027 Uiso 1 1 calc R U . . .
C1 C 0.7302(3) 0.3871(4) 0.79324(14) 0.0192(5) Uani 1 1 d . . . . .
H1A H 0.6778 0.4787 0.8338 0.023 Uiso 1 1 calc R U . . .
H1B H 0.8093 0.2936 0.8258 0.023 Uiso 1 1 calc R U . . .
C6 C 0.5452(3) 0.0093(4) 0.62869(13) 0.0148(5) Uani 1 1 d . . . . .
H6 H 0.6030 -0.1158 0.6103 0.018 Uiso 1 1 calc R U . . .
C18 C 0.6820(3) 0.2565(4) 0.54886(13) 0.0179(5) Uani 1 1 d . . . . .
H18A H 0.6538 0.4001 0.5475 0.021 Uiso 1 1 calc R U . . .
H18B H 0.7402 0.2216 0.4964 0.021 Uiso 1 1 calc R U . . .
C7 C 0.3765(3) -0.0447(4) 0.66826(13) 0.0144(5) Uani 1 1 d . . . . .
H7 H 0.2885 -0.1175 0.6359 0.017 Uiso 1 1 calc R U . . .
C15 C 0.3343(3) 0.2810(4) 0.85071(13) 0.0181(5) Uani 1 1 d . . . . .
H15A H 0.4038 0.3843 0.8824 0.022 Uiso 1 1 calc R U . . .
H15B H 0.2499 0.3484 0.8098 0.022 Uiso 1 1 calc R U . . .
C16 C 0.2301(3) 0.1566(4) 0.91290(13) 0.0198(5) Uani 1 1 d . . . . .
H16A H 0.2808 0.1776 0.9714 0.024 Uiso 1 1 calc R U . . .
H16B H 0.1046 0.2001 0.9103 0.024 Uiso 1 1 calc R U . . .
C12 C 0.4331(3) -0.1304(4) 0.90852(14) 0.0192(5) Uani 1 1 d . . . . .
H12A H 0.4501 -0.2636 0.8838 0.023 Uiso 1 1 calc R U . . .
H12B H 0.4591 -0.1397 0.9705 0.023 Uiso 1 1 calc R U . . .
C11 C 0.5632(3) 0.0191(4) 0.87033(13) 0.0160(5) Uani 1 1 d . . . . .
H11A H 0.6162 0.1058 0.9156 0.019 Uiso 1 1 calc R U . . .
H11B H 0.6604 -0.0541 0.8448 0.019 Uiso 1 1 calc R U . . .
C20 C 0.4618(3) 0.4215(4) 0.69446(14) 0.0181(5) Uani 1 1 d . . . . .
H20A H 0.4289 0.5288 0.7323 0.027 Uiso 1 1 calc R U . . .
H20B H 0.3543 0.3544 0.6713 0.027 Uiso 1 1 calc R U . . .
H20C H 0.5263 0.4770 0.6480 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1S H1SA 0.9247 . ?
O1S H1SB 0.8377 . ?
O4 C4 1.446(3) . ?
O4 H4 0.8400 . ?
O6 C18 1.452(2) . ?
O6 C6 1.457(3) . ?
C17 C13 1.528(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C13 C16 1.529(4) . ?
C13 C12 1.538(3) . ?
C13 C14 1.540(3) . ?
C14 C8 1.514(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C8 C7 1.330(3) . ?
C8 C9 1.525(3) . ?
C9 C11 1.552(3) . ?
C9 C10 1.555(3) . ?
C9 C15 1.557(3) . ?
C10 C1 1.538(3) . ?
C10 C20 1.547(3) . ?
C10 C5 1.553(3) . ?
C5 C6 1.512(3) . ?
C5 C4 1.530(3) . ?
C5 H5 1.0000 . ?
C4 C3 1.535(4) . ?
C4 C18 1.545(3) . ?
C3 C2 1.534(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2 C1 1.536(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C6 C7 1.498(3) . ?
C6 H6 1.0000 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C7 H7 0.9500 . ?
C15 C16 1.543(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C12 C11 1.554(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1SA O1S H1SB 105.7 . . ?
C4 O4 H4 109.5 . . ?
C18 O6 C6 108.74(15) . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C17 C13 C16 111.54(19) . . ?
C17 C13 C12 111.29(19) . . ?
C16 C13 C12 107.32(19) . . ?
C17 C13 C14 111.06(19) . . ?
C16 C13 C14 107.7(2) . . ?
C12 C13 C14 107.78(17) . . ?
C8 C14 C13 109.16(17) . . ?
C8 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C8 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C7 C8 C14 122.4(2) . . ?
C7 C8 C9 124.45(18) . . ?
C14 C8 C9 113.00(18) . . ?
C8 C9 C11 106.8(2) . . ?
C8 C9 C10 109.68(17) . . ?
C11 C9 C10 115.13(16) . . ?
C8 C9 C15 106.83(15) . . ?
C11 C9 C15 105.52(17) . . ?
C10 C9 C15 112.42(19) . . ?
C1 C10 C20 107.9(2) . . ?
C1 C10 C5 106.15(16) . . ?
C20 C10 C5 114.28(17) . . ?
C1 C10 C9 114.30(17) . . ?
C20 C10 C9 107.83(16) . . ?
C5 C10 C9 106.59(19) . . ?
C6 C5 C4 102.30(16) . . ?
C6 C5 C10 112.09(16) . . ?
C4 C5 C10 115.9(2) . . ?
C6 C5 H5 108.7 . . ?
C4 C5 H5 108.7 . . ?
C10 C5 H5 108.7 . . ?
O4 C4 C5 106.0(2) . . ?
O4 C4 C3 108.20(16) . . ?
C5 C4 C3 114.19(18) . . ?
O4 C4 C18 107.69(18) . . ?
C5 C4 C18 102.37(15) . . ?
C3 C4 C18 117.7(2) . . ?
C2 C3 C4 116.37(17) . . ?
C2 C3 H3A 108.2 . . ?
C4 C3 H3A 108.2 . . ?
C2 C3 H3B 108.2 . . ?
C4 C3 H3B 108.2 . . ?
H3A C3 H3B 107.3 . . ?
C3 C2 C1 112.5(2) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C2 C1 C10 110.51(18) . . ?
C2 C1 H1A 109.5 . . ?
C10 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C10 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
O6 C6 C7 114.29(17) . . ?
O6 C6 C5 104.10(19) . . ?
C7 C6 C5 113.26(17) . . ?
O6 C6 H6 108.3 . . ?
C7 C6 H6 108.3 . . ?
C5 C6 H6 108.3 . . ?
O6 C18 C4 106.69(18) . . ?
O6 C18 H18A 110.4 . . ?
C4 C18 H18A 110.4 . . ?
O6 C18 H18B 110.4 . . ?
C4 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?
C8 C7 C6 122.1(2) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C16 C15 C9 111.0(2) . . ?
C16 C15 H15A 109.4 . . ?
C9 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C9 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C13 C16 C15 110.08(18) . . ?
C13 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C13 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
C13 C12 C11 110.64(19) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C9 C11 C12 109.67(16) . . ?
C9 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C9 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 C13 C14 C8 -168.5(2) . . . . ?
C16 C13 C14 C8 69.1(2) . . . . ?
C12 C13 C14 C8 -46.4(3) . . . . ?
C13 C14 C8 C7 157.0(2) . . . . ?
C13 C14 C8 C9 -19.4(3) . . . . ?
C7 C8 C9 C11 -108.0(3) . . . . ?
C14 C8 C9 C11 68.3(2) . . . . ?
C7 C8 C9 C10 17.4(3) . . . . ?
C14 C8 C9 C10 -166.34(19) . . . . ?
C7 C8 C9 C15 139.5(2) . . . . ?
C14 C8 C9 C15 -44.2(3) . . . . ?
C8 C9 C10 C1 -168.3(2) . . . . ?
C11 C9 C10 C1 -47.8(3) . . . . ?
C15 C9 C10 C1 73.0(2) . . . . ?
C8 C9 C10 C20 71.8(2) . . . . ?
C11 C9 C10 C20 -167.8(2) . . . . ?
C15 C9 C10 C20 -46.9(2) . . . . ?
C8 C9 C10 C5 -51.3(2) . . . . ?
C11 C9 C10 C5 69.1(2) . . . . ?
C15 C9 C10 C5 -170.02(15) . . . . ?
C1 C10 C5 C6 -173.25(19) . . . . ?
C20 C10 C5 C6 -54.5(2) . . . . ?
C9 C10 C5 C6 64.5(2) . . . . ?
C1 C10 C5 C4 -56.3(2) . . . . ?
C20 C10 C5 C4 62.4(2) . . . . ?
C9 C10 C5 C4 -178.56(16) . . . . ?
C6 C5 C4 O4 -77.4(2) . . . . ?
C10 C5 C4 O4 160.35(16) . . . . ?
C6 C5 C4 C3 163.6(2) . . . . ?
C10 C5 C4 C3 41.3(2) . . . . ?
C6 C5 C4 C18 35.3(2) . . . . ?
C10 C5 C4 C18 -86.9(2) . . . . ?
O4 C4 C3 C2 -150.48(19) . . . . ?
C5 C4 C3 C2 -32.7(3) . . . . ?
C18 C4 C3 C2 87.3(2) . . . . ?
C4 C3 C2 C1 41.6(3) . . . . ?
C3 C2 C1 C10 -58.4(3) . . . . ?
C20 C10 C1 C2 -59.0(2) . . . . ?
C5 C10 C1 C2 63.9(3) . . . . ?
C9 C10 C1 C2 -178.95(19) . . . . ?
C18 O6 C6 C7 152.3(2) . . . . ?
C18 O6 C6 C5 28.2(2) . . . . ?
C4 C5 C6 O6 -39.5(2) . . . . ?
C10 C5 C6 O6 85.3(2) . . . . ?
C4 C5 C6 C7 -164.2(2) . . . . ?
C10 C5 C6 C7 -39.4(3) . . . . ?
C6 O6 C18 C4 -5.4(2) . . . . ?
O4 C4 C18 O6 92.30(19) . . . . ?
C5 C4 C18 O6 -19.2(2) . . . . ?
C3 C4 C18 O6 -145.21(19) . . . . ?
C14 C8 C7 C6 -166.6(2) . . . . ?
C9 C8 C7 C6 9.3(4) . . . . ?
O6 C6 C7 C8 -117.1(2) . . . . ?
C5 C6 C7 C8 1.9(4) . . . . ?
C8 C9 C15 C16 64.9(2) . . . . ?
C11 C9 C15 C16 -48.5(2) . . . . ?
C10 C9 C15 C16 -174.78(16) . . . . ?
C17 C13 C16 C15 -170.00(17) . . . . ?
C12 C13 C16 C15 67.9(2) . . . . ?
C14 C13 C16 C15 -47.9(2) . . . . ?
C9 C15 C16 C13 -16.8(2) . . . . ?
C17 C13 C12 C11 -170.0(2) . . . . ?
C16 C13 C12 C11 -47.7(2) . . . . ?
C14 C13 C12 C11 68.0(3) . . . . ?
C8 C9 C11 C12 -45.1(2) . . . . ?
C10 C9 C11 C12 -167.07(19) . . . . ?
C15 C9 C11 C12 68.4(2) . . . . ?
C13 C12 C11 C9 -18.7(3) . . . . ?

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
C18 H18A O6 0.99 2.60 3.386(3) 136.2 2_656
O4 H4 O1S 0.84 1.93 2.769(2) 172.8 1_655
O1S H1SB O6 0.84 2.00 2.826(2) 169.4 .
O1S H1SA O4 0.92 1.94 2.845(3) 167.4 2_656
O1S H1SB O6 0.84 2.00 2.826(2) 169.4 .
O1S H1SA O4 0.92 1.94 2.845(3) 167.4 2_656
C18 H18A O6 0.99 2.60 3.386(3) 136.2 2_656
O4 H4 O1S 0.84 1.93 2.769(2) 172.8 1_655
C18 H18A O6 0.99 2.60 3.386(3) 136.2 2_656
O4 H4 O1S 0.84 1.93 2.769(2) 172.8 1_655
C18 H18A O6 0.99 2.60 3.386(3) 136.2 2_656
O4 H4 O1S 0.84 1.93 2.769(2) 172.8 1_655
O4 H4 O1S 0.84 1.93 2.769(2) 172.8 1_655
C18 H18A O6 0.99 2.60 3.386(3) 136.2 2_656
O4 H4 O1S 0.84 1.93 2.769(2) 172.8 1_655
C18 H18A O6 0.99 2.60 3.386(3) 136.2 2_656
O4 H4 O1S 0.84 1.93 2.769(2) 172.8 1_655
C18 H18A O6 0.99 2.60 3.386(3) 136.2 2_656
O1S H1SA O4 0.92 1.94 2.845(3) 167.4 2_656
O1S H1SB O6 0.84 2.00 2.826(2) 169.4 .
O1S H1SA O4 0.92 1.94 2.845(3) 167.4 2_656
O1S H1SB O6 0.84 2.00 2.826(2) 169.4 .
O4 H4 O1S 0.84 1.93 2.769(2) 172.8 1_655
C18 H18A O6 0.99 2.60 3.386(3) 136.2 2_656

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.047


_chemical_compound_source        'Xylaria longipes'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_lchb31_0m
_database_code_depnum_ccdc_archive 'CCDC 1963365'
loop_
_audit_author_name
_audit_author_address
'Xiao-Nian Li'
;Kunming Institute of Botany, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2020-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Xylarilongipin B'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H28 O3'
_chemical_formula_sum            'C20 H28 O3'
_chemical_formula_weight         316.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.6786(3)
_cell_length_b                   10.5655(4)
_cell_length_c                   40.1904(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3260.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      4.33
_cell_measurement_theta_max      68.99

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   0.5110
_exptl_transmission_factor_max   0.7532
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.669
_shelx_estimated_absorpt_T_min   0.710
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16385
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         4.327
_diffrn_reflns_theta_max         69.270
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_point_group_measured_fraction_full 0.917
_reflns_number_total             5475
_reflns_number_gt                4758
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.629
_reflns_Friedel_fraction_max     0.812
_reflns_Friedel_fraction_full    0.840

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1428P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1569 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5475
_refine_ls_number_parameters     423
_refine_ls_number_restraints     276
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.2112
_refine_ls_wR_factor_gt          0.1827
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7399(5) 0.4238(3) 0.14200(7) 0.0194(8) Uani 1 1 d . U . . .
H1 H 0.8038 0.3624 0.1473 0.029 Uiso 1 1 calc R U . . .
O2 O 0.1603(5) 0.2248(3) 0.10238(7) 0.0192(8) Uani 1 1 d . U . . .
O3 O 0.1558(5) 0.3352(3) 0.05505(7) 0.0147(7) Uani 1 1 d . U . . .
O4 O 0.9234(5) 1.1928(3) 0.15461(7) 0.0180(8) Uani 1 1 d . U . . .
H4 H 0.9947 1.1912 0.1387 0.027 Uiso 1 1 calc R U . . .
O5 O 0.6625(5) 0.8201(3) 0.09058(7) 0.0218(8) Uani 1 1 d . U . . .
O6 O 0.5038(5) 0.7500(3) 0.13361(7) 0.0179(8) Uani 1 1 d . U . . .
C17 C 0.6895(7) 0.6469(4) -0.07234(10) 0.0161(10) Uani 1 1 d . U . . .
H17A H 0.6959 0.5790 -0.0889 0.024 Uiso 1 1 calc R U . . .
H17B H 0.8000 0.6933 -0.0720 0.024 Uiso 1 1 calc R U . . .
H17C H 0.5947 0.7049 -0.0781 0.024 Uiso 1 1 calc R U . . .
C13 C 0.6552(7) 0.5899(4) -0.03807(9) 0.0123(10) Uani 1 1 d . U . . .
C14 C 0.4879(7) 0.5108(4) -0.03806(9) 0.0139(10) Uani 1 1 d . U . . .
H14A H 0.3930 0.5582 -0.0492 0.017 Uiso 1 1 calc R U . . .
H14B H 0.5069 0.4309 -0.0504 0.017 Uiso 1 1 calc R U . . .
C8 C 0.4379(6) 0.4822(4) -0.00234(10) 0.0112(9) Uani 1 1 d . U . . .
C9 C 0.5926(6) 0.4944(4) 0.02140(9) 0.0102(10) Uani 1 1 d . U . . .
C10 C 0.5452(6) 0.4314(4) 0.05549(9) 0.0110(9) Uani 1 1 d . U . . .
C1 C 0.6769(6) 0.4621(4) 0.08359(9) 0.0132(10) Uani 1 1 d . U . . .
H1A H 0.7960 0.4389 0.0764 0.016 Uiso 1 1 calc R U . . .
H1B H 0.6750 0.5539 0.0884 0.016 Uiso 1 1 calc R U . . .
C2 C 0.6281(7) 0.3874(4) 0.11496(10) 0.0156(10) Uani 1 1 d . U . . .
H2 H 0.6420 0.2948 0.1106 0.019 Uiso 1 1 calc R U . . .
C19 C 0.2025(7) 0.3189(5) 0.08708(10) 0.0147(10) Uani 1 1 d . U . . .
C6 C 0.2219(6) 0.4580(4) 0.04284(10) 0.0116(10) Uani 1 1 d . U . . .
H6 H 0.1282 0.5228 0.0458 0.014 Uiso 1 1 calc R U . . .
C5 C 0.3693(6) 0.4888(4) 0.06682(9) 0.0095(9) Uani 1 1 d . U . . .
H5 H 0.3813 0.5827 0.0689 0.011 Uiso 1 1 calc R U . . .
C4 C 0.3011(6) 0.4345(4) 0.09966(10) 0.0128(10) Uani 1 1 d . U . . .
C18 C 0.1599(7) 0.5217(5) 0.11502(10) 0.0181(11) Uani 1 1 d . U . . .
H18A H 0.1174 0.4844 0.1358 0.027 Uiso 1 1 calc R U . . .
H18B H 0.0629 0.5306 0.0994 0.027 Uiso 1 1 calc R U . . .
H18C H 0.2102 0.6051 0.1196 0.027 Uiso 1 1 calc R U . . .
C3 C 0.4417(7) 0.4140(5) 0.12632(10) 0.0164(11) Uani 1 1 d . U . . .
H3A H 0.4443 0.4903 0.1406 0.020 Uiso 1 1 calc R U . . .
H3B H 0.4041 0.3424 0.1405 0.020 Uiso 1 1 calc R U . . .
C20 C 0.5394(7) 0.2866(4) 0.05039(10) 0.0123(10) Uani 1 1 d . U . . .
H20A H 0.4840 0.2467 0.0697 0.018 Uiso 1 1 calc R U . . .
H20B H 0.6582 0.2541 0.0479 0.018 Uiso 1 1 calc R U . . .
H20C H 0.4722 0.2671 0.0303 0.018 Uiso 1 1 calc R U . . .
C16 C 0.6326(7) 0.6958(4) -0.01171(9) 0.0118(10) Uani 1 1 d . U . . .
H16A H 0.7273 0.7587 -0.0140 0.014 Uiso 1 1 calc R U . . .
H16B H 0.5202 0.7396 -0.0152 0.014 Uiso 1 1 calc R U . . .
C15 C 0.6373(7) 0.6375(4) 0.02350(9) 0.0125(10) Uani 1 1 d . U . . .
H15A H 0.5520 0.6810 0.0380 0.015 Uiso 1 1 calc R U . . .
H15B H 0.7546 0.6486 0.0333 0.015 Uiso 1 1 calc R U . . .
C12 C 0.8063(7) 0.5069(5) -0.02654(10) 0.0153(10) Uani 1 1 d . U . . .
H12A H 0.9073 0.5606 -0.0206 0.018 Uiso 1 1 calc R U . . .
H12B H 0.8419 0.4493 -0.0447 0.018 Uiso 1 1 calc R U . . .
C11 C 0.7486(6) 0.4287(4) 0.00413(9) 0.0134(10) Uani 1 1 d . U . . .
H11A H 0.8468 0.4212 0.0200 0.016 Uiso 1 1 calc R U . . .
H11B H 0.7146 0.3425 -0.0030 0.016 Uiso 1 1 calc R U . . .
C7 C 0.2755(6) 0.4577(4) 0.00720(10) 0.0136(10) Uani 1 1 d . U . . .
H7 H 0.1906 0.4392 -0.0093 0.016 Uiso 1 1 calc R U . . .
C21 C 0.0447(7) 0.9471(5) 0.28462(10) 0.0217(12) Uani 1 1 d . U . . .
H21A H 0.0694 1.0058 0.3029 0.032 Uiso 1 1 calc R U . . .
H21B H 0.0474 0.8600 0.2930 0.032 Uiso 1 1 calc R U . . .
H21C H -0.0708 0.9654 0.2754 0.032 Uiso 1 1 calc R U . . .
C22 C 0.1831(7) 0.9631(5) 0.25723(10) 0.0164(11) Uani 1 1 d . U . . .
C23 C 0.1455(7) 0.8694(5) 0.22853(10) 0.0166(10) Uani 1 1 d . U . . .
H23A H 0.1220 0.7839 0.2376 0.020 Uiso 1 1 calc R U . . .
H23B H 0.0421 0.8974 0.2158 0.020 Uiso 1 1 calc R U . . .
C24 C 0.3041(7) 0.8659(4) 0.20605(10) 0.0141(10) Uani 1 1 d . U . . .
C25 C 0.4148(7) 0.9843(4) 0.20875(10) 0.0153(10) Uani 1 1 d . U . . .
C26 C 0.5419(7) 0.9893(4) 0.17854(9) 0.0144(10) Uani 1 1 d . U . . .
C27 C 0.6836(7) 1.0923(5) 0.18139(10) 0.0159(10) Uani 1 1 d . U . . .
H27A H 0.6278 1.1756 0.1851 0.019 Uiso 1 1 calc R U . . .
H27B H 0.7593 1.0738 0.2007 0.019 Uiso 1 1 calc R U . . .
C28 C 0.7943(7) 1.0976(5) 0.14972(10) 0.0168(10) Uani 1 1 d . U . . .
H28 H 0.7184 1.1225 0.1306 0.020 Uiso 1 1 calc R U . . .
C29 C 0.6447(7) 0.8096(5) 0.12029(10) 0.0161(10) Uani 1 1 d . U . . .
C30 C 0.5168(7) 0.7540(5) 0.17024(10) 0.0157(11) Uani 1 1 d . U . . .
H30 H 0.5748 0.6744 0.1779 0.019 Uiso 1 1 calc R U . . .
C31 C 0.6382(7) 0.8638(4) 0.17710(10) 0.0132(10) Uani 1 1 d . U . . .
H31 H 0.7007 0.8492 0.1986 0.016 Uiso 1 1 calc R U . . .
C32 C 0.7674(7) 0.8520(5) 0.14802(10) 0.0185(11) Uani 1 1 d . U . . .
C33 C 0.8782(7) 0.9701(4) 0.14214(10) 0.0146(10) Uani 1 1 d . U . . .
H33A H 0.9849 0.9625 0.1558 0.018 Uiso 1 1 calc R U . . .
H33B H 0.9149 0.9703 0.1185 0.018 Uiso 1 1 calc R U . . .
C34 C 0.3452(7) 0.7648(5) 0.18751(10) 0.0152(10) Uani 1 1 d . U . . .
H34 H 0.2629 0.6982 0.1853 0.018 Uiso 1 1 calc R U . . .
C35 C 0.3681(7) 0.9353(5) 0.26972(10) 0.0187(11) Uani 1 1 d . U . . .
H35A H 0.3813 0.8434 0.2738 0.022 Uiso 1 1 calc R U . . .
H35B H 0.3882 0.9802 0.2910 0.022 Uiso 1 1 calc R U . . .
C36 C 0.5035(7) 0.9792(5) 0.24369(9) 0.0164(10) Uani 1 1 d . U . . .
H36A H 0.6028 0.9194 0.2432 0.020 Uiso 1 1 calc R U . . .
H36B H 0.5484 1.0640 0.2497 0.020 Uiso 1 1 calc R U . . .
C37 C 0.1816(7) 1.0951(4) 0.24268(10) 0.0172(10) Uani 1 1 d . U . . .
H37A H 0.2315 1.1555 0.2589 0.021 Uiso 1 1 calc R U . . .
H37B H 0.0603 1.1211 0.2379 0.021 Uiso 1 1 calc R U . . .
C38 C 0.2898(7) 1.0978(5) 0.21012(10) 0.0176(11) Uani 1 1 d . U . . .
H38A H 0.2104 1.0952 0.1907 0.021 Uiso 1 1 calc R U . . .
H38B H 0.3574 1.1775 0.2090 0.021 Uiso 1 1 calc R U . . .
C39 C 0.4313(7) 1.0205(5) 0.14718(10) 0.0151(10) Uani 1 1 d . U . . .
H39A H 0.5009 1.0051 0.1271 0.023 Uiso 1 1 calc R U . . .
H39B H 0.3958 1.1095 0.1478 0.023 Uiso 1 1 calc R U . . .
H39C H 0.3276 0.9665 0.1468 0.023 Uiso 1 1 calc R U . . .
C40 C 0.8911(7) 0.7386(4) 0.15231(11) 0.0175(11) Uani 1 1 d . U . . .
H40A H 0.9759 0.7378 0.1341 0.026 Uiso 1 1 calc R U . . .
H40B H 0.8237 0.6599 0.1520 0.026 Uiso 1 1 calc R U . . .
H40C H 0.9524 0.7459 0.1736 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.437(5) . ?
O1 H1 0.8400 . ?
O2 C19 1.213(6) . ?
O3 C19 1.347(5) . ?
O3 C6 1.477(5) . ?
O4 C28 1.426(6) . ?
O4 H4 0.8400 . ?
O5 C29 1.207(5) . ?
O6 C29 1.361(6) . ?
O6 C30 1.476(5) . ?
C17 C13 1.526(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C13 C12 1.526(7) . ?
C13 C14 1.532(7) . ?
C13 C16 1.550(5) . ?
C14 C8 1.517(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C8 C7 1.330(7) . ?
C8 C9 1.529(6) . ?
C9 C11 1.549(6) . ?
C9 C15 1.552(6) . ?
C9 C10 1.566(5) . ?
C10 C20 1.545(6) . ?
C10 C5 1.549(6) . ?
C10 C1 1.550(6) . ?
C1 C2 1.533(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.529(7) . ?
C2 H2 1.0000 . ?
C19 C4 1.524(6) . ?
C6 C7 1.490(5) . ?
C6 C5 1.522(6) . ?
C6 H6 1.0000 . ?
C5 C4 1.531(5) . ?
C5 H5 1.0000 . ?
C4 C3 1.536(6) . ?
C4 C18 1.550(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C16 C15 1.544(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C12 C11 1.548(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C7 H7 0.9500 . ?
C21 C22 1.539(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C37 1.512(6) . ?
C22 C35 1.535(7) . ?
C22 C23 1.547(6) . ?
C23 C24 1.517(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C34 1.340(7) . ?
C24 C25 1.516(6) . ?
C25 C38 1.537(7) . ?
C25 C26 1.559(6) . ?
C25 C36 1.561(6) . ?
C26 C31 1.520(6) . ?
C26 C27 1.543(7) . ?
C26 C39 1.555(6) . ?
C27 C28 1.532(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C33 1.524(7) . ?
C28 H28 1.0000 . ?
C29 C32 1.527(6) . ?
C30 C34 1.494(7) . ?
C30 C31 1.514(6) . ?
C30 H30 1.0000 . ?
C31 C32 1.537(6) . ?
C31 H31 1.0000 . ?
C32 C33 1.528(7) . ?
C32 C40 1.539(7) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34 0.9500 . ?
C35 C36 1.546(7) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.550(6) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C19 O3 C6 109.8(3) . . ?
C28 O4 H4 109.5 . . ?
C29 O6 C30 109.0(3) . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C17 C13 C12 111.7(4) . . ?
C17 C13 C14 111.1(4) . . ?
C12 C13 C14 108.9(4) . . ?
C17 C13 C16 110.6(4) . . ?
C12 C13 C16 107.0(4) . . ?
C14 C13 C16 107.4(4) . . ?
C8 C14 C13 108.7(3) . . ?
C8 C14 H14A 109.9 . . ?
C13 C14 H14A 109.9 . . ?
C8 C14 H14B 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C7 C8 C14 123.3(4) . . ?
C7 C8 C9 124.4(4) . . ?
C14 C8 C9 112.1(4) . . ?
C8 C9 C11 106.5(3) . . ?
C8 C9 C15 106.7(3) . . ?
C11 C9 C15 106.8(4) . . ?
C8 C9 C10 109.2(4) . . ?
C11 C9 C10 112.5(4) . . ?
C15 C9 C10 114.7(3) . . ?
C20 C10 C5 113.7(4) . . ?
C20 C10 C1 108.8(4) . . ?
C5 C10 C1 105.8(3) . . ?
C20 C10 C9 108.1(3) . . ?
C5 C10 C9 107.1(4) . . ?
C1 C10 C9 113.4(4) . . ?
C2 C1 C10 109.4(4) . . ?
C2 C1 H1A 109.8 . . ?
C10 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
C10 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
O1 C2 C3 106.5(3) . . ?
O1 C2 C1 109.8(4) . . ?
C3 C2 C1 112.3(4) . . ?
O1 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
O2 C19 O3 121.2(4) . . ?
O2 C19 C4 128.4(4) . . ?
O3 C19 C4 110.3(3) . . ?
O3 C6 C7 114.3(3) . . ?
O3 C6 C5 103.4(3) . . ?
C7 C6 C5 113.8(4) . . ?
O3 C6 H6 108.3 . . ?
C7 C6 H6 108.3 . . ?
C5 C6 H6 108.3 . . ?
C6 C5 C4 102.2(4) . . ?
C6 C5 C10 112.3(3) . . ?
C4 C5 C10 113.9(4) . . ?
C6 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
C10 C5 H5 109.4 . . ?
C19 C4 C5 100.6(3) . . ?
C19 C4 C3 117.9(4) . . ?
C5 C4 C3 114.4(4) . . ?
C19 C4 C18 105.1(4) . . ?
C5 C4 C18 111.1(4) . . ?
C3 C4 C18 107.3(3) . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C3 C4 118.4(3) . . ?
C2 C3 H3A 107.7 . . ?
C4 C3 H3A 107.7 . . ?
C2 C3 H3B 107.7 . . ?
C4 C3 H3B 107.7 . . ?
H3A C3 H3B 107.1 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C16 C13 109.6(4) . . ?
C15 C16 H16A 109.7 . . ?
C13 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C13 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C16 C15 C9 109.5(3) . . ?
C16 C15 H15A 109.8 . . ?
C9 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C9 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C13 C12 C11 109.3(4) . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C12 C11 C9 109.8(4) . . ?
C12 C11 H11A 109.7 . . ?
C9 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C9 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C8 C7 C6 122.4(4) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C37 C22 C35 108.0(4) . . ?
C37 C22 C21 111.9(4) . . ?
C35 C22 C21 112.6(4) . . ?
C37 C22 C23 107.5(3) . . ?
C35 C22 C23 107.1(4) . . ?
C21 C22 C23 109.5(4) . . ?
C24 C23 C22 108.1(4) . . ?
C24 C23 H23A 110.1 . . ?
C22 C23 H23A 110.1 . . ?
C24 C23 H23B 110.1 . . ?
C22 C23 H23B 110.1 . . ?
H23A C23 H23B 108.4 . . ?
C34 C24 C25 124.4(5) . . ?
C34 C24 C23 122.6(5) . . ?
C25 C24 C23 112.8(4) . . ?
C24 C25 C38 107.2(4) . . ?
C24 C25 C26 108.8(4) . . ?
C38 C25 C26 113.1(4) . . ?
C24 C25 C36 106.3(3) . . ?
C38 C25 C36 105.5(3) . . ?
C26 C25 C36 115.4(4) . . ?
C31 C26 C27 106.0(4) . . ?
C31 C26 C39 114.8(3) . . ?
C27 C26 C39 107.2(4) . . ?
C31 C26 C25 107.8(4) . . ?
C27 C26 C25 114.0(3) . . ?
C39 C26 C25 107.3(4) . . ?
C28 C27 C26 110.8(3) . . ?
C28 C27 H27A 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?
O4 C28 C33 110.9(4) . . ?
O4 C28 C27 107.3(3) . . ?
C33 C28 C27 111.6(4) . . ?
O4 C28 H28 109.0 . . ?
C33 C28 H28 109.0 . . ?
C27 C28 H28 109.0 . . ?
O5 C29 O6 121.5(4) . . ?
O5 C29 C32 128.7(5) . . ?
O6 C29 C32 109.8(4) . . ?
O6 C30 C34 114.0(4) . . ?
O6 C30 C31 104.2(3) . . ?
C34 C30 C31 113.6(4) . . ?
O6 C30 H30 108.3 . . ?
C34 C30 H30 108.3 . . ?
C31 C30 H30 108.3 . . ?
C30 C31 C26 112.1(4) . . ?
C30 C31 C32 101.4(3) . . ?
C26 C31 C32 114.4(4) . . ?
C30 C31 H31 109.6 . . ?
C26 C31 H31 109.6 . . ?
C32 C31 H31 109.6 . . ?
C29 C32 C33 118.0(4) . . ?
C29 C32 C31 100.4(4) . . ?
C33 C32 C31 114.3(4) . . ?
C29 C32 C40 103.5(4) . . ?
C33 C32 C40 108.0(4) . . ?
C31 C32 C40 112.1(4) . . ?
C28 C33 C32 117.1(4) . . ?
C28 C33 H33A 108.0 . . ?
C32 C33 H33A 108.0 . . ?
C28 C33 H33B 108.0 . . ?
C32 C33 H33B 108.0 . . ?
H33A C33 H33B 107.3 . . ?
C24 C34 C30 121.8(5) . . ?
C24 C34 H34 119.1 . . ?
C30 C34 H34 119.1 . . ?
C22 C35 C36 110.1(3) . . ?
C22 C35 H35A 109.6 . . ?
C36 C35 H35A 109.6 . . ?
C22 C35 H35B 109.6 . . ?
C36 C35 H35B 109.6 . . ?
H35A C35 H35B 108.2 . . ?
C35 C36 C25 109.0(4) . . ?
C35 C36 H36A 109.9 . . ?
C25 C36 H36A 109.9 . . ?
C35 C36 H36B 109.9 . . ?
C25 C36 H36B 109.9 . . ?
H36A C36 H36B 108.3 . . ?
C22 C37 C38 109.9(4) . . ?
C22 C37 H37A 109.7 . . ?
C38 C37 H37A 109.7 . . ?
C22 C37 H37B 109.7 . . ?
C38 C37 H37B 109.7 . . ?
H37A C37 H37B 108.2 . . ?
C25 C38 C37 110.5(3) . . ?
C25 C38 H38A 109.5 . . ?
C37 C38 H38A 109.5 . . ?
C25 C38 H38B 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 108.1 . . ?
C26 C39 H39A 109.5 . . ?
C26 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C26 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C32 C40 H40A 109.5 . . ?
C32 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C32 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 C13 C14 C8 -167.1(4) . . . . ?
C12 C13 C14 C8 69.5(4) . . . . ?
C16 C13 C14 C8 -46.0(5) . . . . ?
C13 C14 C8 C7 154.8(4) . . . . ?
C13 C14 C8 C9 -21.1(5) . . . . ?
C7 C8 C9 C11 140.1(5) . . . . ?
C14 C8 C9 C11 -44.1(5) . . . . ?
C7 C8 C9 C15 -106.1(5) . . . . ?
C14 C8 C9 C15 69.7(5) . . . . ?
C7 C8 C9 C10 18.4(6) . . . . ?
C14 C8 C9 C10 -165.8(4) . . . . ?
C8 C9 C10 C20 71.1(5) . . . . ?
C11 C9 C10 C20 -46.9(5) . . . . ?
C15 C9 C10 C20 -169.3(4) . . . . ?
C8 C9 C10 C5 -51.8(4) . . . . ?
C11 C9 C10 C5 -169.8(3) . . . . ?
C15 C9 C10 C5 67.9(5) . . . . ?
C8 C9 C10 C1 -168.2(4) . . . . ?
C11 C9 C10 C1 73.8(5) . . . . ?
C15 C9 C10 C1 -48.5(5) . . . . ?
C20 C10 C1 C2 -54.8(5) . . . . ?
C5 C10 C1 C2 67.7(4) . . . . ?
C9 C10 C1 C2 -175.2(4) . . . . ?
C10 C1 C2 O1 -174.8(4) . . . . ?
C10 C1 C2 C3 -56.5(5) . . . . ?
C6 O3 C19 O2 179.1(5) . . . . ?
C6 O3 C19 C4 2.0(5) . . . . ?
C19 O3 C6 C7 145.3(4) . . . . ?
C19 O3 C6 C5 21.0(4) . . . . ?
O3 C6 C5 C4 -34.7(4) . . . . ?
C7 C6 C5 C4 -159.3(4) . . . . ?
O3 C6 C5 C10 87.8(4) . . . . ?
C7 C6 C5 C10 -36.8(5) . . . . ?
C20 C10 C5 C6 -56.4(5) . . . . ?
C1 C10 C5 C6 -175.8(3) . . . . ?
C9 C10 C5 C6 63.0(4) . . . . ?
C20 C10 C5 C4 59.2(5) . . . . ?
C1 C10 C5 C4 -60.2(5) . . . . ?
C9 C10 C5 C4 178.5(4) . . . . ?
O2 C19 C4 C5 159.4(5) . . . . ?
O3 C19 C4 C5 -23.7(5) . . . . ?
O2 C19 C4 C3 34.3(7) . . . . ?
O3 C19 C4 C3 -148.8(4) . . . . ?
O2 C19 C4 C18 -85.1(6) . . . . ?
O3 C19 C4 C18 91.7(4) . . . . ?
C6 C5 C4 C19 34.7(4) . . . . ?
C10 C5 C4 C19 -86.7(4) . . . . ?
C6 C5 C4 C3 162.1(4) . . . . ?
C10 C5 C4 C3 40.7(5) . . . . ?
C6 C5 C4 C18 -76.2(4) . . . . ?
C10 C5 C4 C18 162.4(4) . . . . ?
O1 C2 C3 C4 156.6(4) . . . . ?
C1 C2 C3 C4 36.4(6) . . . . ?
C19 C4 C3 C2 89.7(5) . . . . ?
C5 C4 C3 C2 -28.2(6) . . . . ?
C18 C4 C3 C2 -152.0(4) . . . . ?
C17 C13 C16 C15 -168.0(4) . . . . ?
C12 C13 C16 C15 -46.2(5) . . . . ?
C14 C13 C16 C15 70.6(5) . . . . ?
C13 C16 C15 C9 -21.3(6) . . . . ?
C8 C9 C15 C16 -43.7(5) . . . . ?
C11 C9 C15 C16 69.9(5) . . . . ?
C10 C9 C15 C16 -164.8(4) . . . . ?
C17 C13 C12 C11 -167.5(4) . . . . ?
C14 C13 C12 C11 -44.4(5) . . . . ?
C16 C13 C12 C11 71.4(5) . . . . ?
C13 C12 C11 C9 -22.3(5) . . . . ?
C8 C9 C11 C12 68.8(5) . . . . ?
C15 C9 C11 C12 -44.9(4) . . . . ?
C10 C9 C11 C12 -171.6(4) . . . . ?
C14 C8 C7 C6 -166.1(4) . . . . ?
C9 C8 C7 C6 9.3(7) . . . . ?
O3 C6 C7 C8 -118.6(5) . . . . ?
C5 C6 C7 C8 0.0(6) . . . . ?
C37 C22 C23 C24 71.0(5) . . . . ?
C35 C22 C23 C24 -44.9(5) . . . . ?
C21 C22 C23 C24 -167.3(4) . . . . ?
C22 C23 C24 C34 153.0(4) . . . . ?
C22 C23 C24 C25 -23.1(5) . . . . ?
C34 C24 C25 C38 142.1(4) . . . . ?
C23 C24 C25 C38 -41.8(4) . . . . ?
C34 C24 C25 C26 19.4(6) . . . . ?
C23 C24 C25 C26 -164.5(4) . . . . ?
C34 C24 C25 C36 -105.5(5) . . . . ?
C23 C24 C25 C36 70.6(5) . . . . ?
C24 C25 C26 C31 -52.5(5) . . . . ?
C38 C25 C26 C31 -171.6(4) . . . . ?
C36 C25 C26 C31 66.8(5) . . . . ?
C24 C25 C26 C27 -169.9(4) . . . . ?
C38 C25 C26 C27 71.1(5) . . . . ?
C36 C25 C26 C27 -50.5(5) . . . . ?
C24 C25 C26 C39 71.6(5) . . . . ?
C38 C25 C26 C39 -47.4(5) . . . . ?
C36 C25 C26 C39 -169.0(4) . . . . ?
C31 C26 C27 C28 65.8(4) . . . . ?
C39 C26 C27 C28 -57.2(5) . . . . ?
C25 C26 C27 C28 -175.8(4) . . . . ?
C26 C27 C28 O4 -178.9(4) . . . . ?
C26 C27 C28 C33 -57.1(5) . . . . ?
C30 O6 C29 O5 -179.0(4) . . . . ?
C30 O6 C29 C32 2.9(5) . . . . ?
C29 O6 C30 C34 146.0(4) . . . . ?
C29 O6 C30 C31 21.7(5) . . . . ?
O6 C30 C31 C26 86.0(4) . . . . ?
C34 C30 C31 C26 -38.5(4) . . . . ?
O6 C30 C31 C32 -36.4(4) . . . . ?
C34 C30 C31 C32 -161.0(4) . . . . ?
C27 C26 C31 C30 -173.4(3) . . . . ?
C39 C26 C31 C30 -55.3(5) . . . . ?
C25 C26 C31 C30 64.2(4) . . . . ?
C27 C26 C31 C32 -58.7(4) . . . . ?
C39 C26 C31 C32 59.4(5) . . . . ?
C25 C26 C31 C32 178.9(4) . . . . ?
O5 C29 C32 C33 31.8(8) . . . . ?
O6 C29 C32 C33 -150.3(4) . . . . ?
O5 C29 C32 C31 156.6(5) . . . . ?
O6 C29 C32 C31 -25.5(5) . . . . ?
O5 C29 C32 C40 -87.5(6) . . . . ?
O6 C29 C32 C40 90.5(5) . . . . ?
C30 C31 C32 C29 36.6(4) . . . . ?
C26 C31 C32 C29 -84.2(5) . . . . ?
C30 C31 C32 C33 164.0(4) . . . . ?
C26 C31 C32 C33 43.2(6) . . . . ?
C30 C31 C32 C40 -72.7(5) . . . . ?
C26 C31 C32 C40 166.5(4) . . . . ?
O4 C28 C33 C32 159.5(3) . . . . ?
C27 C28 C33 C32 39.9(5) . . . . ?
C29 C32 C33 C28 84.9(5) . . . . ?
C31 C32 C33 C28 -32.7(5) . . . . ?
C40 C32 C33 C28 -158.2(4) . . . . ?
C25 C24 C34 C30 6.7(7) . . . . ?
C23 C24 C34 C30 -169.1(4) . . . . ?
O6 C30 C34 C24 -116.5(5) . . . . ?
C31 C30 C34 C24 2.6(6) . . . . ?
C37 C22 C35 C36 -44.3(5) . . . . ?
C21 C22 C35 C36 -168.3(4) . . . . ?
C23 C22 C35 C36 71.3(5) . . . . ?
C22 C35 C36 C25 -23.2(5) . . . . ?
C24 C25 C36 C35 -42.7(5) . . . . ?
C38 C25 C36 C35 71.0(5) . . . . ?
C26 C25 C36 C35 -163.4(4) . . . . ?
C35 C22 C37 C38 69.0(4) . . . . ?
C21 C22 C37 C38 -166.6(4) . . . . ?
C23 C22 C37 C38 -46.3(5) . . . . ?
C24 C25 C38 C37 66.3(4) . . . . ?
C26 C25 C38 C37 -173.7(4) . . . . ?
C36 C25 C38 C37 -46.6(5) . . . . ?
C22 C37 C38 C25 -19.7(5) . . . . ?

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
O4 H4 O2 0.84 1.97 2.798(4) 168.4 1_665
O1 H1 O4 0.84 2.04 2.863(5) 168.4 1_545
O4 H4 O2 0.84 1.97 2.798(4) 168.4 1_665
O1 H1 O4 0.84 2.04 2.863(5) 168.4 1_545
O1 H1 O4 0.84 2.04 2.863(5) 168.4 1_545
O4 H4 O2 0.84 1.97 2.798(4) 168.4 1_665
O1 H1 O4 0.84 2.04 2.863(5) 168.4 1_545
O4 H4 O2 0.84 1.97 2.798(4) 168.4 1_665

_refine_diff_density_max         0.520
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.112


_chemical_compound_source        'Xylaria longipes'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_X73
_database_code_depnum_ccdc_archive 'CCDC 1977046'
loop_
_audit_author_name
_audit_author_address
'Juan He'
;School of Pharmaceutical Sciences, South Central University for Nationalities
China
;
_audit_update_record             
;
2020-01-12 deposited with the CCDC.	2020-03-09 downloaded from the CCDC.
;
_chemical_name_systematic        'Hymatoxin L'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H30 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         318.44
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.5943(6)
_cell_length_b                   6.2502(3)
_cell_length_c                   12.5743(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.5160(10)
_cell_angle_gamma                90
_cell_volume                     868.97(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      3.9981
_cell_measurement_theta_max      79.4058
_cell_measurement_temperature    152.(2)

_exptl_crystal_description       Prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.099
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348

_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      152.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            18724
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         79.39
_diffrn_reflns_theta_full        79.39
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             3681
_reflns_number_gt                3636
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0804
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_number_reflns         3681
_refine_ls_number_parameters     214
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    undef
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.1089P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.143
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.021(2)
_refine_ls_abs_structure_details 
;

Flack x determined using 1615 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.86739(10) 0.83361(17) 0.92526(9) 0.0228(2) Uani d . . . 1 . .
C C1 0.57663(13) 0.3823(3) 0.85465(13) 0.0236(3) Uani d . . . 1 . .
H H1A 0.504668 0.365803 0.788547 0.028 Uiso calc U . R 1 . .
H H1B 0.59994 0.238868 0.887526 0.028 Uiso calc U . R 1 . .
C C2 0.54583(13) 0.5279(3) 0.94034(13) 0.0250(3) Uani d . . . 1 . .
H H2A 0.520562 0.669922 0.906453 0.03 Uiso calc U . R 1 . .
H H2B 0.47721 0.465862 0.961382 0.03 Uiso calc U . R 1 . .
O O2 0.76695(11) 0.99510(18) 1.02858(9) 0.0274(3) Uani d . . . 1 . .
C C3 0.65427(13) 0.5549(3) 1.04502(12) 0.0234(3) Uani d . . . 1 . .
H H3A 0.662854 0.422617 1.090062 0.028 Uiso calc U . R 1 . .
H H3B 0.636479 0.673261 1.09 0.028 Uiso calc U . R 1 . .
O O3 0.80724(14) 0.0066(3) 0.26250(12) 0.0485(4) Uani d . . . 1 . .
H H3 0.770(3) 0.008(5) 0.193(3) 0.073 Uiso calc U . R 1 . .
C C4 0.77560(13) 0.6012(2) 1.02444(11) 0.0198(3) Uani d . . . 1 . .
C C5 0.79367(12) 0.4830(2) 0.92426(11) 0.0187(3) Uani d . . . 1 . .
H H5 0.821009 0.333291 0.946254 0.022 Uiso calc U . R 1 . .
C C11 0.62343(14) 0.3072(3) 0.62235(14) 0.0321(4) Uani d . . . 1 . .
H H11A 0.555986 0.223361 0.634383 0.038 Uiso calc U . R 1 . .
H H11B 0.591195 0.448846 0.592508 0.038 Uiso calc U . R 1 . .
C C6 0.89547(13) 0.6080(2) 0.90170(12) 0.0213(3) Uani d . . . 1 . .
H H6 0.972708 0.565539 0.958717 0.026 Uiso calc U . R 1 . .
C C12 0.67052(15) 0.1922(3) 0.53622(13) 0.0305(4) Uani d . . . 1 . .
H H12A 0.603774 0.178222 0.465673 0.037 Uiso calc U . R 1 . .
H H12B 0.696924 0.046275 0.563491 0.037 Uiso calc U . R 1 . .
C C7 0.90875(13) 0.5674(3) 0.78894(13) 0.0243(3) Uani d . . . 1 . .
H H7 0.9685 0.643145 0.766416 0.029 Uiso calc U . R 1 . .
C C13 0.77654(13) 0.3101(3) 0.51292(12) 0.0245(3) Uani d . . . 1 . .
C C8 0.83788(13) 0.4259(2) 0.71894(12) 0.0223(3) Uani d . . . 1 . .
C C9 0.72177(13) 0.3383(2) 0.73508(12) 0.0218(3) Uani d . . . 1 . .
H H9 0.741086 0.193464 0.76961 0.026 Uiso calc U . R 1 . .
C C10 0.68157(12) 0.4790(2) 0.81900(12) 0.0192(3) Uani d . . . 1 . .
C C20 0.64065(13) 0.7010(2) 0.76592(12) 0.0230(3) Uani d . . . 1 . .
H H20A 0.6993 0.753464 0.72992 0.034 Uiso calc U . R 1 . .
H H20B 0.635768 0.801845 0.824085 0.034 Uiso calc U . R 1 . .
H H20C 0.561009 0.687908 0.710231 0.034 Uiso calc U . R 1 . .
C C15 0.82874(15) 0.1765(3) 0.43527(14) 0.0287(3) Uani d . . . 1 . .
H H15A 0.902237 0.249296 0.428988 0.034 Uiso calc U . R 1 . .
H H15B 0.854109 0.035941 0.470977 0.034 Uiso calc U . R 1 . .
C C19 0.79843(13) 0.8302(2) 0.99489(11) 0.0205(3) Uani d . . . 1 . .
C C18 0.87802(14) 0.5511(3) 1.13324(12) 0.0265(3) Uani d . . . 1 . .
H H18A 0.876874 0.398242 1.150337 0.04 Uiso calc U . R 1 . .
H H18B 0.865656 0.634934 1.194752 0.04 Uiso calc U . R 1 . .
H H18C 0.95629 0.5883 1.12342 0.04 Uiso calc U . R 1 . .
C C17 0.7393(2) 0.5323(3) 0.46313(16) 0.0403(4) Uani d . . . 1 . .
H H17A 0.806261 0.596229 0.441713 0.06 Uiso calc U . R 1 . .
H H17B 0.719519 0.62337 0.518627 0.06 Uiso calc U . R 1 . .
H H17C 0.668369 0.519444 0.397165 0.06 Uiso calc U . R 1 . .
C C16 0.74498(17) 0.1377(3) 0.31877(14) 0.0356(4) Uani d . . . 1 . .
H H16A 0.670134 0.065752 0.322268 0.043 Uiso calc U . R 1 . .
H H16B 0.722573 0.275265 0.278875 0.043 Uiso calc U . R 1 . .
C C14 0.87698(13) 0.3319(3) 0.62490(13) 0.0273(3) Uani d . . . 1 . .
H H14A 0.911715 0.188358 0.647895 0.033 Uiso calc U . R 1 . .
H H14B 0.942151 0.422512 0.613244 0.033 Uiso calc U . R 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C19 . 1.3519(18) ?
O1 C6 . 1.4966(17) ?
C1 C2 . 1.533(2) ?
C1 C10 . 1.5410(19) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.532(2) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
O2 C19 . 1.212(2) ?
C3 C4 . 1.533(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
O3 C16 . 1.414(2) ?
O3 H3 . 0.85(4) ?
C4 C19 . 1.522(2) ?
C4 C5 . 1.5281(19) ?
C4 C18 . 1.5499(19) ?
C5 C6 . 1.512(2) ?
C5 C10 . 1.5512(18) ?
C5 H5 . 1.0 ?
C11 C12 . 1.531(2) ?
C11 C9 . 1.541(2) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C6 C7 . 1.493(2) ?
C6 H6 . 1.0 ?
C12 C13 . 1.535(2) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C7 C8 . 1.340(2) ?
C7 H7 . 0.95 ?
C13 C17 . 1.531(2) ?
C13 C14 . 1.540(2) ?
C13 C15 . 1.540(2) ?
C8 C14 . 1.507(2) ?
C8 C9 . 1.522(2) ?
C9 C10 . 1.5490(19) ?
C9 H9 . 1.0 ?
C10 C20 . 1.551(2) ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C15 C16 . 1.514(2) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C19 O1 C6 . . 108.64(11) ?
C2 C1 C10 . . 110.06(12) ?
C2 C1 H1A . . 109.6 ?
C10 C1 H1A . . 109.6 ?
C2 C1 H1B . . 109.6 ?
C10 C1 H1B . . 109.6 ?
H1A C1 H1B . . 108.2 ?
C3 C2 C1 . . 111.40(12) ?
C3 C2 H2A . . 109.3 ?
C1 C2 H2A . . 109.3 ?
C3 C2 H2B . . 109.3 ?
C1 C2 H2B . . 109.3 ?
H2A C2 H2B . . 108.0 ?
C2 C3 C4 . . 115.69(12) ?
C2 C3 H3A . . 108.4 ?
C4 C3 H3A . . 108.4 ?
C2 C3 H3B . . 108.4 ?
C4 C3 H3B . . 108.4 ?
H3A C3 H3B . . 107.4 ?
C16 O3 H3 . . 109.5 ?
C19 C4 C5 . . 100.15(11) ?
C19 C4 C3 . . 117.06(12) ?
C5 C4 C3 . . 114.11(12) ?
C19 C4 C18 . . 105.21(12) ?
C5 C4 C18 . . 111.79(12) ?
C3 C4 C18 . . 108.13(12) ?
C6 C5 C4 . . 102.32(12) ?
C6 C5 C10 . . 110.45(11) ?
C4 C5 C10 . . 115.07(11) ?
C6 C5 H5 . . 109.6 ?
C4 C5 H5 . . 109.6 ?
C10 C5 H5 . . 109.6 ?
C12 C11 C9 . . 112.80(13) ?
C12 C11 H11A . . 109.0 ?
C9 C11 H11A . . 109.0 ?
C12 C11 H11B . . 109.0 ?
C9 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
C7 C6 O1 . . 116.04(12) ?
C7 C6 C5 . . 113.56(12) ?
O1 C6 C5 . . 102.77(11) ?
C7 C6 H6 . . 108.0 ?
O1 C6 H6 . . 108.0 ?
C5 C6 H6 . . 108.0 ?
C11 C12 C13 . . 112.73(14) ?
C11 C12 H12A . . 109.0 ?
C13 C12 H12A . . 109.0 ?
C11 C12 H12B . . 109.0 ?
C13 C12 H12B . . 109.0 ?
H12A C12 H12B . . 107.8 ?
C8 C7 C6 . . 121.18(14) ?
C8 C7 H7 . . 119.4 ?
C6 C7 H7 . . 119.4 ?
C17 C13 C12 . . 111.72(15) ?
C17 C13 C14 . . 109.65(14) ?
C12 C13 C14 . . 107.26(12) ?
C17 C13 C15 . . 110.40(14) ?
C12 C13 C15 . . 110.54(13) ?
C14 C13 C15 . . 107.12(13) ?
C7 C8 C14 . . 120.18(14) ?
C7 C8 C9 . . 122.79(13) ?
C14 C8 C9 . . 116.82(12) ?
C8 C9 C11 . . 111.22(12) ?
C8 C9 C10 . . 110.26(11) ?
C11 C9 C10 . . 114.04(12) ?
C8 C9 H9 . . 107.0 ?
C11 C9 H9 . . 107.0 ?
C10 C9 H9 . . 107.0 ?
C1 C10 C9 . . 113.67(12) ?
C1 C10 C20 . . 108.06(11) ?
C9 C10 C20 . . 109.29(11) ?
C1 C10 C5 . . 106.88(11) ?
C9 C10 C5 . . 104.12(11) ?
C20 C10 C5 . . 114.95(11) ?
C10 C20 H20A . . 109.5 ?
C10 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C10 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C16 C15 C13 . . 116.12(14) ?
C16 C15 H15A . . 108.3 ?
C13 C15 H15A . . 108.3 ?
C16 C15 H15B . . 108.3 ?
C13 C15 H15B . . 108.3 ?
H15A C15 H15B . . 107.4 ?
O2 C19 O1 . . 120.80(14) ?
O2 C19 C4 . . 128.45(13) ?
O1 C19 C4 . . 110.69(12) ?
C4 C18 H18A . . 109.5 ?
C4 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C4 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C13 C17 H17A . . 109.5 ?
C13 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C13 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O3 C16 C15 . . 107.55(15) ?
O3 C16 H16A . . 110.2 ?
C15 C16 H16A . . 110.2 ?
O3 C16 H16B . . 110.2 ?
C15 C16 H16B . . 110.2 ?
H16A C16 H16B . . 108.5 ?
C8 C14 C13 . . 115.38(12) ?
C8 C14 H14A . . 108.4 ?
C13 C14 H14A . . 108.4 ?
C8 C14 H14B . . 108.4 ?
C13 C14 H14B . . 108.4 ?
H14A C14 H14B . . 107.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 C3 . . . . -60.24(16) ?
C1 C2 C3 C4 . . . . 45.83(18) ?
C2 C3 C4 C19 . . . . 79.57(17) ?
C2 C3 C4 C5 . . . . -36.88(18) ?
C2 C3 C4 C18 . . . . -161.94(13) ?
C19 C4 C5 C6 . . . . 36.56(13) ?
C3 C4 C5 C6 . . . . 162.46(12) ?
C18 C4 C5 C6 . . . . -74.45(15) ?
C19 C4 C5 C10 . . . . -83.24(14) ?
C3 C4 C5 C10 . . . . 42.66(17) ?
C18 C4 C5 C10 . . . . 165.75(12) ?
C19 O1 C6 C7 . . . . 148.00(12) ?
C19 O1 C6 C5 . . . . 23.47(14) ?
C4 C5 C6 C7 . . . . -163.47(12) ?
C10 C5 C6 C7 . . . . -40.49(16) ?
C4 C5 C6 O1 . . . . -37.32(13) ?
C10 C5 C6 O1 . . . . 85.65(13) ?
C9 C11 C12 C13 . . . . -58.2(2) ?
O1 C6 C7 C8 . . . . -121.12(16) ?
C5 C6 C7 C8 . . . . -2.3(2) ?
C11 C12 C13 C17 . . . . -62.47(18) ?
C11 C12 C13 C14 . . . . 57.71(19) ?
C11 C12 C13 C15 . . . . 174.17(14) ?
C6 C7 C8 C14 . . . . -159.39(15) ?
C6 C7 C8 C9 . . . . 15.3(2) ?
C7 C8 C9 C11 . . . . 143.40(17) ?
C14 C8 C9 C11 . . . . -41.79(19) ?
C7 C8 C9 C10 . . . . 15.9(2) ?
C14 C8 C9 C10 . . . . -169.31(13) ?
C12 C11 C9 C8 . . . . 47.2(2) ?
C12 C11 C9 C10 . . . . 172.66(14) ?
C2 C1 C10 C9 . . . . 178.11(12) ?
C2 C1 C10 C20 . . . . -60.41(15) ?
C2 C1 C10 C5 . . . . 63.82(15) ?
C8 C9 C10 C1 . . . . -170.75(12) ?
C11 C9 C10 C1 . . . . 63.29(17) ?
C8 C9 C10 C20 . . . . 68.45(14) ?
C11 C9 C10 C20 . . . . -57.50(16) ?
C8 C9 C10 C5 . . . . -54.83(14) ?
C11 C9 C10 C5 . . . . 179.22(13) ?
C6 C5 C10 C1 . . . . -170.82(12) ?
C4 C5 C10 C1 . . . . -55.62(15) ?
C6 C5 C10 C9 . . . . 68.58(14) ?
C4 C5 C10 C9 . . . . -176.21(12) ?
C6 C5 C10 C20 . . . . -50.93(15) ?
C4 C5 C10 C20 . . . . 64.27(16) ?
C17 C13 C15 C16 . . . . -59.8(2) ?
C12 C13 C15 C16 . . . . 64.3(2) ?
C14 C13 C15 C16 . . . . -179.11(16) ?
C6 O1 C19 O2 . . . . 177.88(13) ?
C6 O1 C19 C4 . . . . 0.48(15) ?
C5 C4 C19 O2 . . . . 159.12(15) ?
C3 C4 C19 O2 . . . . 35.2(2) ?
C18 C4 C19 O2 . . . . -84.81(17) ?
C5 C4 C19 O1 . . . . -23.73(14) ?
C3 C4 C19 O1 . . . . -147.60(12) ?
C18 C4 C19 O1 . . . . 92.34(13) ?
C13 C15 C16 O3 . . . . -177.80(16) ?
C7 C8 C14 C13 . . . . -138.95(17) ?
C9 C8 C14 C13 . . . . 46.1(2) ?
C17 C13 C14 C8 . . . . 69.98(19) ?
C12 C13 C14 C8 . . . . -51.51(19) ?
C15 C13 C14 C8 . . . . -170.20(14) ?


_chemical_compound_source        'Xylaria longipes'
