# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_llg14_0m
_database_code_depnum_ccdc_archive 'CCDC 1561836'
_audit_update_record             
;
2017-07-12 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H22 O2'
_chemical_formula_sum            'C15 H22 O2'
_chemical_formula_weight         234.32

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                   7.70800(10)
_cell_length_b                   12.5490(2)
_cell_length_c                   13.1278(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1269.82(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7699
_cell_measurement_theta_min      4.88
_cell_measurement_theta_max      70.19

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   0.2612
_exptl_transmission_factor_max   0.5857
_exptl_crystal_size_max          0.850
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.621
_shelx_estimated_absorpt_T_min   0.620
_shelx_estimated_absorpt_T_max   0.891
_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            8045
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.875
_diffrn_reflns_theta_max         70.187
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2306
_reflns_number_gt                2295
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_max     0.922
_reflns_Friedel_fraction_full    0.957

_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)+(0.1009P)²+0.1800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0064(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 926 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2306
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.0684(2) 0.24653(15) 0.51563(13) 0.0365(5) Uani 1 1 d . . . . .
O2 O 0.5254(2) 0.40443(14) 0.32442(14) 0.0337(5) Uani 1 1 d . . . . .
H7 H 0.558(5) 0.341(3) 0.372(3) 0.051 Uiso 1 1 d . U . . .
C1 C 0.2895(3) 0.52193(16) 0.29879(18) 0.0270(5) Uani 1 1 d . . . . .
H6 H 0.3814 0.5735 0.3172 0.032 Uiso 1 1 calc R U . . .
H1 H 0.1796 0.5438 0.3318 0.032 Uiso 1 1 calc R U . . .
C2 C 0.3402(3) 0.40927(17) 0.33049(18) 0.0250(5) Uani 1 1 d . . . . .
H8 H 0.3006 0.3944 0.4016 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2497(3) 0.33199(16) 0.25387(15) 0.0220(5) Uani 1 1 d . . . . .
C4 C 0.0758(3) 0.28389(14) 0.29473(17) 0.0235(5) Uani 1 1 d . . . . .
H22 H 0.0940 0.2098 0.3207 0.028 Uiso 1 1 calc R U . . .
C5 C -0.0134(3) 0.35194(17) 0.37373(18) 0.0238(5) Uani 1 1 d . . . . .
C6 C -0.0121(3) 0.32177(19) 0.48110(18) 0.0292(5) Uani 1 1 d . . . . .
H2 H -0.0785 0.3636 0.5271 0.035 Uiso 1 1 calc R U . . .
C7 C 0.1925(3) 0.40399(16) 0.15990(17) 0.0240(5) Uani 1 1 d . . . . .
C8 C 0.2670(4) 0.3666(2) 0.05758(19) 0.0352(6) Uani 1 1 d . . . . .
H4 H 0.2360 0.4179 0.0043 0.053 Uiso 1 1 calc R U . . .
H3 H 0.2189 0.2966 0.0405 0.053 Uiso 1 1 calc R U . . .
H5 H 0.3936 0.3615 0.0626 0.053 Uiso 1 1 calc R U . . .
C9 C 0.2677(3) 0.51537(17) 0.18308(17) 0.0264(5) Uani 1 1 d . . . . .
H9 H 0.3811 0.5247 0.1488 0.032 Uiso 1 1 calc R U . . .
H10 H 0.1877 0.5716 0.1588 0.032 Uiso 1 1 calc R U . . .
C10 C -0.0132(3) 0.39770(17) 0.15983(18) 0.0265(5) Uani 1 1 d . . . . .
C11 C -0.1046(3) 0.47345(17) 0.23524(19) 0.0290(5) Uani 1 1 d . . . . .
H12 H -0.0517 0.5450 0.2289 0.035 Uiso 1 1 calc R U . . .
H11 H -0.2279 0.4798 0.2151 0.035 Uiso 1 1 calc R U . . .
C12 C -0.0971(3) 0.44042(17) 0.34471(19) 0.0282(5) Uani 1 1 d . . . . .
H13 H -0.1528 0.4831 0.3947 0.034 Uiso 1 1 calc R U . . .
C13 C -0.0399(3) 0.28327(16) 0.19956(18) 0.0293(5) Uani 1 1 d . . . . .
H15 H -0.1628 0.2697 0.2171 0.035 Uiso 1 1 calc R U . . .
H14 H -0.0004 0.2296 0.1493 0.035 Uiso 1 1 calc R U . . .
C14 C -0.0937(4) 0.4166(2) 0.0548(2) 0.0377(6) Uani 1 1 d . . . . .
H17 H -0.0487 0.3638 0.0065 0.057 Uiso 1 1 calc R U . . .
H16 H -0.0639 0.4884 0.0311 0.057 Uiso 1 1 calc R U . . .
H18 H -0.2201 0.4098 0.0594 0.057 Uiso 1 1 calc R U . . .
C15 C 0.3689(3) 0.23847(18) 0.22755(19) 0.0312(5) Uani 1 1 d . . . . .
H20 H 0.4739 0.2653 0.1942 0.047 Uiso 1 1 calc R U . . .
H19 H 0.3083 0.1895 0.1815 0.047 Uiso 1 1 calc R U . . .
H21 H 0.4009 0.2006 0.2901 0.047 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 C6 1.217(3) . ?
O2 C2 1.431(3) . ?
O2 H7 1.04(4) . ?
C1 C2 1.525(3) . ?
C1 C9 1.530(3) . ?
C1 H6 0.9900 . ?
C1 H1 0.9900 . ?
C2 C3 1.562(3) . ?
C2 H8 1.0000 . ?
C3 C15 1.530(3) . ?
C3 C4 1.565(3) . ?
C3 C7 1.591(3) . ?
C4 C5 1.509(3) . ?
C4 C13 1.535(3) . ?
C4 H22 1.0000 . ?
C5 C12 1.339(3) . ?
C5 C6 1.460(3) . ?
C6 H2 0.9500 . ?
C7 C8 1.534(3) . ?
C7 C9 1.544(3) . ?
C7 C10 1.587(3) . ?
C8 H4 0.9800 . ?
C8 H3 0.9800 . ?
C8 H5 0.9800 . ?
C9 H9 0.9900 . ?
C9 H10 0.9900 . ?
C10 C14 1.531(3) . ?
C10 C13 1.541(3) . ?
C10 C11 1.543(3) . ?
C11 C12 1.497(3) . ?
C11 H12 0.9900 . ?
C11 H11 0.9900 . ?
C12 H13 0.9500 . ?
C13 H15 0.9900 . ?
C13 H14 0.9900 . ?
C14 H17 0.9800 . ?
C14 H16 0.9800 . ?
C14 H18 0.9800 . ?
C15 H20 0.9800 . ?
C15 H19 0.9800 . ?
C15 H21 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 O2 H7 104(2) . . ?
C2 C1 C9 104.42(18) . . ?
C2 C1 H6 110.9 . . ?
C9 C1 H6 110.9 . . ?
C2 C1 H1 110.9 . . ?
C9 C1 H1 110.9 . . ?
H6 C1 H1 108.9 . . ?
O2 C2 C1 106.26(18) . . ?
O2 C2 C3 112.55(18) . . ?
C1 C2 C3 106.58(18) . . ?
O2 C2 H8 110.4 . . ?
C1 C2 H8 110.4 . . ?
C3 C2 H8 110.4 . . ?
C15 C3 C2 110.68(18) . . ?
C15 C3 C4 107.23(17) . . ?
C2 C3 C4 113.67(17) . . ?
C15 C3 C7 115.26(17) . . ?
C2 C3 C7 105.69(17) . . ?
C4 C3 C7 104.33(15) . . ?
C5 C4 C13 107.32(18) . . ?
C5 C4 C3 114.06(16) . . ?
C13 C4 C3 102.73(17) . . ?
C5 C4 H22 110.8 . . ?
C13 C4 H22 110.8 . . ?
C3 C4 H22 110.8 . . ?
C12 C5 C6 119.6(2) . . ?
C12 C5 C4 119.5(2) . . ?
C6 C5 C4 120.91(19) . . ?
O1 C6 C5 124.4(2) . . ?
O1 C6 H2 117.8 . . ?
C5 C6 H2 117.8 . . ?
C8 C7 C9 107.99(18) . . ?
C8 C7 C10 111.0(2) . . ?
C9 C7 C10 114.86(18) . . ?
C8 C7 C3 113.67(17) . . ?
C9 C7 C3 104.91(17) . . ?
C10 C7 C3 104.40(16) . . ?
C7 C8 H4 109.5 . . ?
C7 C8 H3 109.5 . . ?
H4 C8 H3 109.5 . . ?
C7 C8 H5 109.5 . . ?
H4 C8 H5 109.5 . . ?
H3 C8 H5 109.5 . . ?
C1 C9 C7 106.59(17) . . ?
C1 C9 H9 110.4 . . ?
C7 C9 H9 110.4 . . ?
C1 C9 H10 110.4 . . ?
C7 C9 H10 110.4 . . ?
H9 C9 H10 108.6 . . ?
C14 C10 C13 113.29(19) . . ?
C14 C10 C11 107.3(2) . . ?
C13 C10 C11 107.22(19) . . ?
C14 C10 C7 113.4(2) . . ?
C13 C10 C7 100.33(18) . . ?
C11 C10 C7 115.17(19) . . ?
C12 C11 C10 115.32(18) . . ?
C12 C11 H12 108.4 . . ?
C10 C11 H12 108.4 . . ?
C12 C11 H11 108.4 . . ?
C10 C11 H11 108.4 . . ?
H12 C11 H11 107.5 . . ?
C5 C12 C11 121.4(2) . . ?
C5 C12 H13 119.3 . . ?
C11 C12 H13 119.3 . . ?
C4 C13 C10 101.14(17) . . ?
C4 C13 H15 111.5 . . ?
C10 C13 H15 111.5 . . ?
C4 C13 H14 111.5 . . ?
C10 C13 H14 111.5 . . ?
H15 C13 H14 109.4 . . ?
C10 C14 H17 109.5 . . ?
C10 C14 H16 109.5 . . ?
H17 C14 H16 109.5 . . ?
C10 C14 H18 109.5 . . ?
H17 C14 H18 109.5 . . ?
H16 C14 H18 109.5 . . ?
C3 C15 H20 109.5 . . ?
C3 C15 H19 109.5 . . ?
H20 C15 H19 109.5 . . ?
C3 C15 H21 109.5 . . ?
H20 C15 H21 109.5 . . ?
H19 C15 H21 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
C9 C1 C2 O2 88.9(2) . . . . ?
C9 C1 C2 C3 -31.4(2) . . . . ?
O2 C2 C3 C15 25.5(2) . . . . ?
C1 C2 C3 C15 141.61(19) . . . . ?
O2 C2 C3 C4 146.24(18) . . . . ?
C1 C2 C3 C4 -97.7(2) . . . . ?
O2 C2 C3 C7 -99.9(2) . . . . ?
C1 C2 C3 C7 16.2(2) . . . . ?
C15 C3 C4 C5 148.30(19) . . . . ?
C2 C3 C4 C5 25.6(3) . . . . ?
C7 C3 C4 C5 -89.0(2) . . . . ?
C15 C3 C4 C13 -95.91(18) . . . . ?
C2 C3 C4 C13 141.43(17) . . . . ?
C7 C3 C4 C13 26.8(2) . . . . ?
C13 C4 C5 C12 -38.1(3) . . . . ?
C3 C4 C5 C12 75.0(3) . . . . ?
C13 C4 C5 C6 140.95(19) . . . . ?
C3 C4 C5 C6 -106.0(2) . . . . ?
C12 C5 C6 O1 -175.5(2) . . . . ?
C4 C5 C6 O1 5.4(3) . . . . ?
C15 C3 C7 C8 0.3(3) . . . . ?
C2 C3 C7 C8 122.8(2) . . . . ?
C4 C3 C7 C8 -117.0(2) . . . . ?
C15 C3 C7 C9 -117.5(2) . . . . ?
C2 C3 C7 C9 5.1(2) . . . . ?
C4 C3 C7 C9 125.21(17) . . . . ?
C15 C3 C7 C10 121.3(2) . . . . ?
C2 C3 C7 C10 -116.10(18) . . . . ?
C4 C3 C7 C10 4.0(2) . . . . ?
C2 C1 C9 C7 35.0(2) . . . . ?
C8 C7 C9 C1 -146.06(19) . . . . ?
C10 C7 C9 C1 89.5(2) . . . . ?
C3 C7 C9 C1 -24.5(2) . . . . ?
C8 C7 C10 C14 -31.3(3) . . . . ?
C9 C7 C10 C14 91.5(2) . . . . ?
C3 C7 C10 C14 -154.17(18) . . . . ?
C8 C7 C10 C13 89.8(2) . . . . ?
C9 C7 C10 C13 -147.34(18) . . . . ?
C3 C7 C10 C13 -33.0(2) . . . . ?
C8 C7 C10 C11 -155.47(19) . . . . ?
C9 C7 C10 C11 -32.6(3) . . . . ?
C3 C7 C10 C11 81.7(2) . . . . ?
C14 C10 C11 C12 157.36(19) . . . . ?
C13 C10 C11 C12 35.4(3) . . . . ?
C7 C10 C11 C12 -75.3(2) . . . . ?
C6 C5 C12 C11 -178.90(19) . . . . ?
C4 C5 C12 C11 0.2(3) . . . . ?
C10 C11 C12 C5 1.1(3) . . . . ?
C5 C4 C13 C10 71.9(2) . . . . ?
C3 C4 C13 C10 -48.7(2) . . . . ?
C14 C10 C13 C4 171.6(2) . . . . ?
C11 C10 C13 C4 -70.2(2) . . . . ?
C7 C10 C13 C4 50.4(2) . . . . ?

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
O2 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556
O2 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556
O2 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556
O2 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556
O2 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556
O2 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556
O2 H7 O1 1.04(4) 1.84(4) 2.847(2) 162(3) 2_556

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_llg9_0m
_database_code_depnum_ccdc_archive 'CCDC 1851594'
loop_
_audit_author_name
_audit_author_address
'Xiao-Nian Li'
;Kunming Institute of Botany, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2018-06-26 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 O4'
_chemical_formula_sum            'C16 H24 O4'
_chemical_formula_weight         280.35

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                   6.4948(2)
_cell_length_b                   7.4524(3)
_cell_length_c                   15.2812(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.0040(10)
_cell_angle_gamma                90
_cell_volume                     726.04(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7484
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      70.09

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   0.3130
_exptl_transmission_factor_max   0.5220
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.736
_shelx_estimated_absorpt_T_min   0.650
_shelx_estimated_absorpt_T_max   0.930
_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            7540
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.946
_diffrn_reflns_theta_max         70.141
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.937
_reflns_number_total             2510
_reflns_number_gt                2499
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     0.896
_reflns_Friedel_fraction_full    0.924

_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)+(0.0597P)²+0.1084P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1119 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2510
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.5846(2) 0.1316(2) 0.59832(9) 0.0181(3) Uani 1 1 d . . . . .
H1 H 0.536(4) 0.028(5) 0.5987(18) 0.027 Uiso 1 1 d . U . . .
O2 O 0.9229(2) 0.7489(2) 0.85996(9) 0.0222(3) Uani 1 1 d . . . . .
O3 O 0.4502(2) 0.76548(18) 0.57251(9) 0.0174(3) Uani 1 1 d . . . . .
H12 H 0.427(4) 0.735(4) 0.5175(19) 0.026 Uiso 1 1 d . U . . .
O4 O 0.6740(3) 0.7129(4) 0.94034(11) 0.0595(7) Uani 1 1 d . . . . .
C1 C 0.5797(3) 0.2281(3) 0.67857(12) 0.0138(4) Uani 1 1 d . . . . .
H24 H 0.6816 0.3296 0.6817 0.017 Uiso 1 1 calc R U . . .
C2 C 0.3622(3) 0.3103(2) 0.68590(11) 0.0130(4) Uani 1 1 d . . . . .
C3 C 0.3883(3) 0.3457(3) 0.79015(12) 0.0153(4) Uani 1 1 d . . . . .
C4 C 0.3866(3) 0.5540(3) 0.79626(12) 0.0159(4) Uani 1 1 d . . . . .
H10 H 0.3413 0.5953 0.8519 0.019 Uiso 1 1 calc R U . . .
C5 C 0.5932(3) 0.6371(2) 0.78706(12) 0.0147(4) Uani 1 1 d . . . . .
C6 C 0.7305(3) 0.7020(3) 0.87077(13) 0.0210(4) Uani 1 1 d . . . . .
C7 C 1.0575(4) 0.8213(3) 0.93788(14) 0.0283(5) Uani 1 1 d . . . . .
H20 H 0.9911 0.9272 0.9586 0.042 Uiso 1 1 calc R U . . .
H2 H 1.1923 0.8555 0.9230 0.042 Uiso 1 1 calc R U . . .
H19 H 1.0805 0.7304 0.9851 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2086(3) 0.2727(3) 0.83232(13) 0.0232(4) Uani 1 1 d . . . . .
H3 H 0.1986 0.1424 0.8240 0.035 Uiso 1 1 calc R U . . .
H5 H 0.0764 0.3287 0.8037 0.035 Uiso 1 1 calc R U . . .
H4 H 0.2364 0.3004 0.8962 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5946(3) 0.2506(3) 0.83443(12) 0.0177(4) Uani 1 1 d . . . . .
H9 H 0.7100 0.3385 0.8503 0.021 Uiso 1 1 calc R U . . .
H6 H 0.5760 0.1861 0.8890 0.021 Uiso 1 1 calc R U . . .
C10 C 0.6411(3) 0.1192(3) 0.76398(13) 0.0174(4) Uani 1 1 d . . . . .
H8 H 0.7914 0.0860 0.7748 0.021 Uiso 1 1 calc R U . . .
H7 H 0.5553 0.0091 0.7622 0.021 Uiso 1 1 calc R U . . .
C11 C 0.6454(3) 0.6586(2) 0.70751(12) 0.0143(4) Uani 1 1 d . . . . .
H11 H 0.7770 0.7111 0.7043 0.017 Uiso 1 1 calc R U . . .
C12 C 0.5026(3) 0.6024(2) 0.62263(12) 0.0139(4) Uani 1 1 d . . . . .
H18 H 0.5822 0.5220 0.5886 0.017 Uiso 1 1 calc R U . . .
C13 C 0.3054(3) 0.5005(3) 0.64007(12) 0.0143(4) Uani 1 1 d . . . . .
C14 C 0.2245(3) 0.6033(3) 0.71318(12) 0.0176(4) Uani 1 1 d . . . . .
H14 H 0.0822 0.5630 0.7185 0.021 Uiso 1 1 calc R U . . .
H13 H 0.2223 0.7342 0.7020 0.021 Uiso 1 1 calc R U . . .
C15 C 0.1427(3) 0.4941(3) 0.55302(12) 0.0202(4) Uani 1 1 d . . . . .
H15 H 0.0135 0.4383 0.5642 0.030 Uiso 1 1 calc R U . . .
H17 H 0.1983 0.4235 0.5086 0.030 Uiso 1 1 calc R U . . .
H16 H 0.1124 0.6164 0.5306 0.030 Uiso 1 1 calc R U . . .
C16 C 0.1935(3) 0.1699(3) 0.65168(12) 0.0184(4) Uani 1 1 d . . . . .
H22 H 0.1895 0.1481 0.5881 0.028 Uiso 1 1 calc R U . . .
H23 H 0.0565 0.2141 0.6601 0.028 Uiso 1 1 calc R U . . .
H21 H 0.2267 0.0578 0.6849 0.028 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 C1 1.427(2) . ?
O1 H1 0.84(3) . ?
O2 C6 1.338(3) . ?
O2 C7 1.441(2) . ?
O3 C12 1.442(2) . ?
O3 H12 0.86(3) . ?
O4 C6 1.192(3) . ?
C1 C10 1.524(2) . ?
C1 C2 1.563(2) . ?
C1 H24 1.0000 . ?
C2 C16 1.533(2) . ?
C2 C3 1.592(2) . ?
C2 C13 1.592(2) . ?
C3 C8 1.536(3) . ?
C3 C9 1.552(3) . ?
C3 C4 1.556(3) . ?
C4 C5 1.509(3) . ?
C4 C14 1.531(2) . ?
C4 H10 1.0000 . ?
C5 C11 1.332(3) . ?
C5 C6 1.493(2) . ?
C7 H20 0.9800 . ?
C7 H2 0.9800 . ?
C7 H19 0.9800 . ?
C8 H3 0.9800 . ?
C8 H5 0.9800 . ?
C8 H4 0.9800 . ?
C9 C10 1.527(3) . ?
C9 H9 0.9900 . ?
C9 H6 0.9900 . ?
C10 H8 0.9900 . ?
C10 H7 0.9900 . ?
C11 C12 1.503(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.555(2) . ?
C12 H18 1.0000 . ?
C13 C14 1.528(3) . ?
C13 C15 1.534(2) . ?
C14 H14 0.9900 . ?
C14 H13 0.9900 . ?
C15 H15 0.9800 . ?
C15 H17 0.9800 . ?
C15 H16 0.9800 . ?
C16 H22 0.9800 . ?
C16 H23 0.9800 . ?
C16 H21 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
C1 O1 H1 113.0(19) . . ?
C6 O2 C7 115.43(16) . . ?
C12 O3 H12 106(2) . . ?
O1 C1 C10 115.00(16) . . ?
O1 C1 C2 115.33(14) . . ?
C10 C1 C2 103.88(14) . . ?
O1 C1 H24 107.4 . . ?
C10 C1 H24 107.4 . . ?
C2 C1 H24 107.4 . . ?
C16 C2 C1 107.73(15) . . ?
C16 C2 C3 112.78(15) . . ?
C1 C2 C3 102.21(13) . . ?
C16 C2 C13 111.54(14) . . ?
C1 C2 C13 116.99(14) . . ?
C3 C2 C13 105.33(14) . . ?
C8 C3 C9 108.49(16) . . ?
C8 C3 C4 108.27(16) . . ?
C9 C3 C4 116.42(15) . . ?
C8 C3 C2 114.64(15) . . ?
C9 C3 C2 106.20(15) . . ?
C4 C3 C2 102.99(14) . . ?
C5 C4 C14 107.89(15) . . ?
C5 C4 C3 112.79(15) . . ?
C14 C4 C3 101.61(15) . . ?
C5 C4 H10 111.4 . . ?
C14 C4 H10 111.4 . . ?
C3 C4 H10 111.4 . . ?
C11 C5 C6 121.91(18) . . ?
C11 C5 C4 121.31(17) . . ?
C6 C5 C4 116.70(16) . . ?
O4 C6 O2 123.09(19) . . ?
O4 C6 C5 123.5(2) . . ?
O2 C6 C5 113.44(17) . . ?
O2 C7 H20 109.5 . . ?
O2 C7 H2 109.5 . . ?
H20 C7 H2 109.5 . . ?
O2 C7 H19 109.5 . . ?
H20 C7 H19 109.5 . . ?
H2 C7 H19 109.5 . . ?
C3 C8 H3 109.5 . . ?
C3 C8 H5 109.5 . . ?
H3 C8 H5 109.5 . . ?
C3 C8 H4 109.5 . . ?
H3 C8 H4 109.5 . . ?
H5 C8 H4 109.5 . . ?
C10 C9 C3 104.82(14) . . ?
C10 C9 H9 110.8 . . ?
C3 C9 H9 110.8 . . ?
C10 C9 H6 110.8 . . ?
C3 C9 H6 110.8 . . ?
H9 C9 H6 108.9 . . ?
C1 C10 C9 102.00(15) . . ?
C1 C10 H8 111.4 . . ?
C9 C10 H8 111.4 . . ?
C1 C10 H7 111.4 . . ?
C9 C10 H7 111.4 . . ?
H8 C10 H7 109.2 . . ?
C5 C11 C12 122.11(17) . . ?
C5 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
O3 C12 C11 105.52(14) . . ?
O3 C12 C13 112.59(14) . . ?
C11 C12 C13 112.39(15) . . ?
O3 C12 H18 108.7 . . ?
C11 C12 H18 108.7 . . ?
C13 C12 H18 108.7 . . ?
C14 C13 C15 111.93(15) . . ?
C14 C13 C12 106.84(15) . . ?
C15 C13 C12 108.67(14) . . ?
C14 C13 C2 101.99(14) . . ?
C15 C13 C2 114.66(15) . . ?
C12 C13 C2 112.40(14) . . ?
C13 C14 C4 102.01(14) . . ?
C13 C14 H14 111.4 . . ?
C4 C14 H14 111.4 . . ?
C13 C14 H13 111.4 . . ?
C4 C14 H13 111.4 . . ?
H14 C14 H13 109.2 . . ?
C13 C15 H15 109.5 . . ?
C13 C15 H17 109.5 . . ?
H15 C15 H17 109.5 . . ?
C13 C15 H16 109.5 . . ?
H15 C15 H16 109.5 . . ?
H17 C15 H16 109.5 . . ?
C2 C16 H22 109.5 . . ?
C2 C16 H23 109.5 . . ?
H22 C16 H23 109.5 . . ?
C2 C16 H21 109.5 . . ?
H22 C16 H21 109.5 . . ?
H23 C16 H21 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
O1 C1 C2 C16 42.42(19) . . . . ?
C10 C1 C2 C16 -84.35(17) . . . . ?
O1 C1 C2 C3 161.44(15) . . . . ?
C10 C1 C2 C3 34.67(17) . . . . ?
O1 C1 C2 C13 -84.12(19) . . . . ?
C10 C1 C2 C13 149.10(15) . . . . ?
C16 C2 C3 C8 -14.7(2) . . . . ?
C1 C2 C3 C8 -130.09(17) . . . . ?
C13 C2 C3 C8 107.17(17) . . . . ?
C16 C2 C3 C9 105.08(17) . . . . ?
C1 C2 C3 C9 -10.32(18) . . . . ?
C13 C2 C3 C9 -133.05(15) . . . . ?
C16 C2 C3 C4 -132.07(16) . . . . ?
C1 C2 C3 C4 112.54(15) . . . . ?
C13 C2 C3 C4 -10.20(17) . . . . ?
C8 C3 C4 C5 160.14(15) . . . . ?
C9 C3 C4 C5 37.7(2) . . . . ?
C2 C3 C4 C5 -78.08(17) . . . . ?
C8 C3 C4 C14 -84.61(17) . . . . ?
C9 C3 C4 C14 152.90(15) . . . . ?
C2 C3 C4 C14 37.17(17) . . . . ?
C14 C4 C5 C11 -31.8(2) . . . . ?
C3 C4 C5 C11 79.6(2) . . . . ?
C14 C4 C5 C6 145.21(17) . . . . ?
C3 C4 C5 C6 -103.38(19) . . . . ?
C7 O2 C6 O4 -2.4(3) . . . . ?
C7 O2 C6 C5 176.88(17) . . . . ?
C11 C5 C6 O4 166.8(2) . . . . ?
C4 C5 C6 O4 -10.2(3) . . . . ?
C11 C5 C6 O2 -12.5(3) . . . . ?
C4 C5 C6 O2 170.52(16) . . . . ?
C8 C3 C9 C10 106.20(17) . . . . ?
C4 C3 C9 C10 -131.43(17) . . . . ?
C2 C3 C9 C10 -17.50(19) . . . . ?
O1 C1 C10 C9 -173.41(14) . . . . ?
C2 C1 C10 C9 -46.43(17) . . . . ?
C3 C9 C10 C1 39.21(18) . . . . ?
C6 C5 C11 C12 -176.69(16) . . . . ?
C4 C5 C11 C12 0.2(3) . . . . ?
C5 C11 C12 O3 116.82(18) . . . . ?
C5 C11 C12 C13 -6.2(2) . . . . ?
O3 C12 C13 C14 -75.26(17) . . . . ?
C11 C12 C13 C14 43.73(19) . . . . ?
O3 C12 C13 C15 45.7(2) . . . . ?
C11 C12 C13 C15 164.67(15) . . . . ?
O3 C12 C13 C2 173.67(14) . . . . ?
C11 C12 C13 C2 -67.34(19) . . . . ?
C16 C2 C13 C14 102.20(16) . . . . ?
C1 C2 C13 C14 -133.15(15) . . . . ?
C3 C2 C13 C14 -20.46(17) . . . . ?
C16 C2 C13 C15 -19.0(2) . . . . ?
C1 C2 C13 C15 105.68(17) . . . . ?
C3 C2 C13 C15 -141.64(15) . . . . ?
C16 C2 C13 C12 -143.73(15) . . . . ?
C1 C2 C13 C12 -19.1(2) . . . . ?
C3 C2 C13 C12 93.60(17) . . . . ?
C15 C13 C14 C4 167.24(16) . . . . ?
C12 C13 C14 C4 -73.93(17) . . . . ?
C2 C13 C14 C4 44.19(17) . . . . ?
C5 C4 C14 C13 67.10(18) . . . . ?
C3 C4 C14 C13 -51.71(17) . . . . ?

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
O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656
O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545
O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656
O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545
O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656
O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545
O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656
O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545
O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656
O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545
O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656
O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545
O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545
O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656
O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545
O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656
O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545
O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656
O1 H1 O3 0.84(3) 2.05(4) 2.869(2) 166(3) 1_545
O3 H12 O1 0.86(3) 1.92(3) 2.7632(19) 169(3) 2_656

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.057

