# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_2017941-143-1_0m
_database_code_depnum_ccdc_archive 'CCDC 1825711'
_audit_update_record             
;
2018-02-26 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;
_audit_creation_date             2017-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O5, H2 O'
_chemical_formula_sum            'C18 H18 O6'
_chemical_formula_weight         330.32
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   24.3697(19)
_cell_length_b                   9.1064(7)
_cell_length_c                   6.6779(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.992(4)
_cell_angle_gamma                90
_cell_volume                     1459.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4262
_cell_measurement_temperature    205
_cell_measurement_theta_max      72.869
_cell_measurement_theta_min      3.683
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.777
_exptl_absorpt_coefficient_mu    0.947
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.6053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1278 before and 0.0515 after correction. The Ratio of minimum to maximum transmission is 0.8031. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9163
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        63.978
_diffrn_reflns_theta_max         63.978
_diffrn_reflns_theta_min         3.683
_diffrn_ambient_temperature      205
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                2227
_reflns_number_total             2262
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details 
;
 Flack x determined using 937 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0660P)²+0.0890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0824
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Free rotating group:
 O6(H6A)
2.b Ternary CH refined with riding coordinates:
 C10(H10)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C17(H17)
2.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C1(H1A,H1B,H1C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.48884(7) 0.87885(18) 0.7334(3) 0.0265(4) Uani 1 1 d . . . . .
O4 O 0.26415(6) 0.3862(2) 0.6300(2) 0.0282(4) Uani 1 1 d . . . . .
H4 H 0.2497 0.4378 0.5325 0.042 Uiso 1 1 calc GR . . . .
O5 O 0.28149(7) 0.0826(2) 0.6874(2) 0.0313(4) Uani 1 1 d . . . . .
H5 H 0.2660 0.0773 0.7885 0.047 Uiso 1 1 calc GR . . . .
O3 O 0.53791(6) 0.30532(19) 0.7739(3) 0.0323(4) Uani 1 1 d . . . . .
O2 O 0.61697(6) 0.5055(2) 0.8607(3) 0.0311(4) Uani 1 1 d . . . . .
O6 O 0.22961(7) 0.0588(2) 1.0104(3) 0.0388(5) Uani 1 1 d . . . . .
H6A H 0.1946 0.0618 0.9685 0.058 Uiso 1 1 d G . . . .
C15 C 0.45047(9) 0.6304(3) 0.7059(3) 0.0191(5) Uani 1 1 d . . . . .
C16 C 0.49691(9) 0.7319(2) 0.7447(3) 0.0200(5) Uani 1 1 d . . . . .
C6 C 0.46245(9) 0.4778(3) 0.7204(3) 0.0189(5) Uani 1 1 d . . . . .
C3 C 0.55227(9) 0.7012(3) 0.7935(3) 0.0202(5) Uani 1 1 d . . . . .
C7 C 0.41806(9) 0.3749(3) 0.6857(3) 0.0195(5) Uani 1 1 d . . . . .
C12 C 0.36323(9) 0.4267(2) 0.6328(3) 0.0191(5) Uani 1 1 d . . . . .
C10 C 0.32576(9) 0.1867(3) 0.7247(3) 0.0244(5) Uani 1 1 d . . . . .
H10 H 0.3305 0.2195 0.8680 0.029 Uiso 1 1 calc R . . . .
C2 C 0.58179(9) 0.8393(3) 0.8129(3) 0.0237(5) Uani 1 1 d . . . . .
C11 C 0.31387(8) 0.3202(3) 0.5850(3) 0.0217(5) Uani 1 1 d . . . . .
C13 C 0.35317(9) 0.5776(3) 0.6167(3) 0.0225(5) Uani 1 1 d . . . . .
H13 H 0.3163 0.6112 0.5793 0.027 Uiso 1 1 calc R . . . .
C5 C 0.52220(9) 0.4315(2) 0.7688(3) 0.0201(5) Uani 1 1 d . . . . .
C4 C 0.56953(9) 0.5500(3) 0.8137(3) 0.0200(5) Uani 1 1 d . . . . .
C14 C 0.39602(9) 0.6789(3) 0.6544(3) 0.0221(5) Uani 1 1 d . . . . .
H14 H 0.3882 0.7800 0.6451 0.027 Uiso 1 1 calc R . . . .
C8 C 0.42957(9) 0.2122(3) 0.7114(4) 0.0241(5) Uani 1 1 d . . . . .
H8A H 0.4519 0.1963 0.8465 0.029 Uiso 1 1 calc R . . . .
H8B H 0.4524 0.1822 0.6112 0.029 Uiso 1 1 calc R . . . .
C17 C 0.54179(10) 0.9409(3) 0.7759(4) 0.0272(5) Uani 1 1 d . . . . .
H17 H 0.5486 1.0426 0.7782 0.033 Uiso 1 1 calc R . . . .
C18 C 0.30508(9) 0.2777(3) 0.3604(3) 0.0284(5) Uani 1 1 d . . . . .
H18A H 0.2765 0.2025 0.3337 0.043 Uiso 1 1 calc GR . . . .
H18B H 0.3397 0.2402 0.3273 0.043 Uiso 1 1 calc GR . . . .
H18C H 0.2934 0.3634 0.2776 0.043 Uiso 1 1 calc GR . . . .
C9 C 0.37875(9) 0.1113(3) 0.6891(4) 0.0267(5) Uani 1 1 d . . . . .
H9A H 0.3723 0.0693 0.5519 0.032 Uiso 1 1 calc R . . . .
H9B H 0.3870 0.0300 0.7858 0.032 Uiso 1 1 calc R . . . .
C1 C 0.64360(9) 0.8636(3) 0.8615(4) 0.0316(5) Uani 1 1 d . . . . .
H1A H 0.6582 0.8211 0.9932 0.047 Uiso 1 1 calc GR . . . .
H1B H 0.6513 0.9682 0.8646 0.047 Uiso 1 1 calc GR . . . .
H1C H 0.6612 0.8173 0.7582 0.047 Uiso 1 1 calc GR . . . .
H6B H 0.2337(15) 0.001(6) 1.122(6) 0.062(11) Uiso 1 1 d . . . . .


_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 C16 1.353(3) . ?
O1 C17 1.392(3) . ?
O4 H4 0.8300 . ?
O4 C11 1.431(3) . ?
O5 H5 0.8300 . ?
O5 C10 1.425(3) . ?
O3 C5 1.210(3) . ?
O2 C4 1.214(3) . ?
O6 H6A 0.8500 . ?
O6 H6B 0.90(5) . ?
C15 C16 1.449(3) . ?
C15 C6 1.420(3) . ?
C15 C14 1.384(3) . ?
C16 C3 1.361(3) . ?
C6 C7 1.419(3) . ?
C6 C5 1.496(3) . ?
C3 C2 1.443(3) . ?
C3 C4 1.440(3) . ?
C7 C12 1.403(3) . ?
C7 C8 1.512(3) . ?
C12 C11 1.535(3) . ?
C12 C13 1.397(3) . ?
C10 H10 0.9900 . ?
C10 C11 1.529(3) . ?
C10 C9 1.517(3) . ?
C2 C17 1.336(4) . ?
C2 C1 1.501(3) . ?
C11 C18 1.527(3) . ?
C13 H13 0.9400 . ?
C13 C14 1.383(3) . ?
C5 C4 1.570(3) . ?
C14 H14 0.9400 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 C9 1.528(3) . ?
C17 H17 0.9400 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?

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
C16 O1 C17 105.66(18) . . ?
C11 O4 H4 109.5 . . ?
C10 O5 H5 109.5 . . ?
H6A O6 H6B 104.6 . . ?
C6 C15 C16 117.83(19) . . ?
C14 C15 C16 121.8(2) . . ?
C14 C15 C6 120.4(2) . . ?
O1 C16 C15 121.3(2) . . ?
O1 C16 C3 110.1(2) . . ?
C3 C16 C15 128.6(2) . . ?
C15 C6 C5 118.1(2) . . ?
C7 C6 C15 119.55(19) . . ?
C7 C6 C5 122.3(2) . . ?
C16 C3 C2 107.5(2) . . ?
C16 C3 C4 118.7(2) . . ?
C4 C3 C2 133.80(19) . . ?
C6 C7 C8 120.48(19) . . ?
C12 C7 C6 119.0(2) . . ?
C12 C7 C8 120.50(19) . . ?
C7 C12 C11 121.17(19) . . ?
C13 C12 C7 119.8(2) . . ?
C13 C12 C11 119.0(2) . . ?
O5 C10 H10 109.1 . . ?
O5 C10 C11 111.37(17) . . ?
O5 C10 C9 108.12(19) . . ?
C11 C10 H10 109.1 . . ?
C9 C10 H10 109.1 . . ?
C9 C10 C11 109.92(18) . . ?
C3 C2 C1 127.9(2) . . ?
C17 C2 C3 104.50(18) . . ?
C17 C2 C1 127.6(2) . . ?
O4 C11 C12 110.61(18) . . ?
O4 C11 C10 106.48(17) . . ?
O4 C11 C18 109.47(17) . . ?
C10 C11 C12 108.45(17) . . ?
C18 C11 C12 109.63(17) . . ?
C18 C11 C10 112.2(2) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.7(2) . . ?
C14 C13 H13 119.2 . . ?
O3 C5 C6 124.4(2) . . ?
O3 C5 C4 115.4(2) . . ?
C6 C5 C4 120.2(2) . . ?
O2 C4 C3 126.4(2) . . ?
O2 C4 C5 117.1(2) . . ?
C3 C4 C5 116.53(19) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C7 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
C7 C8 C9 116.54(19) . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
O1 C17 H17 123.9 . . ?
C2 C17 O1 112.2(2) . . ?
C2 C17 H17 123.9 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C9 C8 114.2(2) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2017935_0m
_database_code_depnum_ccdc_archive 'CCDC 1825712'
_audit_update_record             
;
2018-02-26 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;
_audit_creation_date             2017-10-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O5, H2 O'
_chemical_formula_sum            'C18 H18 O6'
_chemical_formula_weight         330.32
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   24.373(2)
_cell_length_b                   9.0977(8)
_cell_length_c                   6.6706(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.828(4)
_cell_angle_gamma                90
_cell_volume                     1457.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3272
_cell_measurement_temperature    205
_cell_measurement_theta_max      69.83
_cell_measurement_theta_min      3.68
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.771
_exptl_absorpt_coefficient_mu    0.948
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.6062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1239 before and 0.0566 after correction. The Ratio of minimum to maximum transmission is 0.8043. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11941
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.122
_diffrn_reflns_theta_min         3.681
_diffrn_ambient_temperature      205
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.812
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                2223
_reflns_number_total             2422
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 835 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2422
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0735
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O6-H6B = O6-H6A
 0.84 with sigma of 0.02
3.a Free rotating group:
 O6(H6A)
3.b Ternary CH refined with riding coordinates:
 C10(H10)
3.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B)
3.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C3(H3)
3.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C1(H1A,H1B,H1C)
3.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O3 O 0.51122(7) 0.12150(18) 0.2668(3) 0.0269(4) Uani 1 1 d . . . . .
O4 O 0.73595(6) 0.6147(2) 0.3702(2) 0.0265(4) Uani 1 1 d . . . . .
H4 H 0.7502 0.5618 0.4666 0.040 Uiso 1 1 calc GR . . . .
O5 O 0.71870(7) 0.91808(19) 0.3134(2) 0.0289(4) Uani 1 1 d . . . . .
H5 H 0.7344 0.9235 0.2126 0.043 Uiso 1 1 calc GR . . . .
O1 O 0.38320(7) 0.4950(2) 0.1386(3) 0.0318(4) Uani 1 1 d . . . . .
O2 O 0.46215(7) 0.6958(2) 0.2264(3) 0.0335(4) Uani 1 1 d . . . . .
O6 O 0.77062(8) 0.9416(2) -0.0108(3) 0.0363(5) Uani 1 1 d D . . . .
H6A H 0.8054 0.9370 0.0323 0.054 Uiso 1 1 d DG . . . .
C4 C 0.50311(10) 0.2684(2) 0.2553(3) 0.0207(5) Uani 1 1 d . . . . .
C8 C 0.63679(9) 0.5738(3) 0.3677(3) 0.0193(5) Uani 1 1 d . . . . .
C13 C 0.58197(9) 0.6258(3) 0.3141(3) 0.0194(5) Uani 1 1 d . . . . .
C5 C 0.54956(9) 0.3707(3) 0.2942(3) 0.0190(5) Uani 1 1 d . . . . .
C17 C 0.44787(10) 0.2997(3) 0.2065(3) 0.0213(5) Uani 1 1 d . . . . .
C9 C 0.68609(9) 0.6803(3) 0.4158(3) 0.0213(5) Uani 1 1 d . . . . .
C16 C 0.43055(9) 0.4508(3) 0.1860(3) 0.0209(5) Uani 1 1 d . . . . .
C7 C 0.64693(9) 0.4233(3) 0.3836(3) 0.0224(5) Uani 1 1 d . . . . .
H7 H 0.6838 0.3897 0.4206 0.027 Uiso 1 1 calc R . . . .
C10 C 0.67435(9) 0.8139(3) 0.2750(3) 0.0232(5) Uani 1 1 d . . . . .
H10 H 0.6699 0.7809 0.1317 0.028 Uiso 1 1 calc R . . . .
C14 C 0.53745(9) 0.5225(3) 0.2794(3) 0.0196(5) Uani 1 1 d . . . . .
C2 C 0.41826(9) 0.1608(3) 0.1874(3) 0.0240(5) Uani 1 1 d . . . . .
C12 C 0.57035(9) 0.7888(3) 0.2880(4) 0.0240(5) Uani 1 1 d . . . . .
H12A H 0.5475 0.8191 0.3883 0.029 Uiso 1 1 calc R . . . .
H12B H 0.5482 0.8047 0.1527 0.029 Uiso 1 1 calc R . . . .
C6 C 0.60394(10) 0.3216(3) 0.3463(3) 0.0233(5) Uani 1 1 d . . . . .
H6 H 0.6117 0.2204 0.3563 0.028 Uiso 1 1 calc R . . . .
C15 C 0.47805(10) 0.5685(3) 0.2311(3) 0.0219(5) Uani 1 1 d . . . . .
C3 C 0.45843(10) 0.0589(3) 0.2244(4) 0.0277(6) Uani 1 1 d . . . . .
H3 H 0.4517 -0.0429 0.2221 0.033 Uiso 1 1 calc R . . . .
C11 C 0.62133(10) 0.8888(3) 0.3102(4) 0.0262(5) Uani 1 1 d . . . . .
H11A H 0.6133 0.9703 0.2136 0.031 Uiso 1 1 calc R . . . .
H11B H 0.6276 0.9309 0.4475 0.031 Uiso 1 1 calc R . . . .
C18 C 0.69474(10) 0.7231(3) 0.6400(3) 0.0277(5) Uani 1 1 d . . . . .
H18A H 0.7067 0.6376 0.7230 0.041 Uiso 1 1 calc GR . . . .
H18B H 0.6600 0.7598 0.6734 0.041 Uiso 1 1 calc GR . . . .
H18C H 0.7230 0.7990 0.6661 0.041 Uiso 1 1 calc GR . . . .
C1 C 0.35657(9) 0.1361(3) 0.1386(4) 0.0309(6) Uani 1 1 d . . . . .
H1A H 0.3386 0.1861 0.2385 0.046 Uiso 1 1 calc GR . . . .
H1B H 0.3488 0.0316 0.1416 0.046 Uiso 1 1 calc GR . . . .
H1C H 0.3423 0.1747 0.0042 0.046 Uiso 1 1 calc GR . . . .
H6B H 0.7644(15) 1.000(4) -0.110(4) 0.057(11) Uiso 1 1 d D . . . .


_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
O3 C4 1.352(3) . ?
O3 C3 1.391(3) . ?
O4 H4 0.8300 . ?
O4 C9 1.432(3) . ?
O5 H5 0.8300 . ?
O5 C10 1.428(3) . ?
O1 C16 1.212(3) . ?
O2 C15 1.219(3) . ?
O6 H6A 0.8496 . ?
O6 H6B 0.84(2) . ?
C4 C5 1.454(3) . ?
C4 C17 1.360(3) . ?
C8 C13 1.405(3) . ?
C8 C9 1.534(3) . ?
C8 C7 1.393(3) . ?
C13 C14 1.424(3) . ?
C13 C12 1.515(4) . ?
C5 C14 1.413(4) . ?
C5 C6 1.385(3) . ?
C17 C16 1.438(4) . ?
C17 C2 1.450(3) . ?
C9 C10 1.533(3) . ?
C9 C18 1.524(3) . ?
C16 C15 1.568(3) . ?
C7 H7 0.9400 . ?
C7 C6 1.388(3) . ?
C10 H10 0.9900 . ?
C10 C11 1.514(3) . ?
C14 C15 1.489(3) . ?
C2 C3 1.340(4) . ?
C2 C1 1.500(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 C11 1.527(3) . ?
C6 H6 0.9400 . ?
C3 H3 0.9400 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?

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
C4 O3 C3 105.79(19) . . ?
C9 O4 H4 109.5 . . ?
C10 O5 H5 109.5 . . ?
H6A O6 H6B 109.3 . . ?
O3 C4 C5 121.4(2) . . ?
O3 C4 C17 110.5(2) . . ?
C17 C4 C5 128.2(2) . . ?
C13 C8 C9 121.2(2) . . ?
C7 C8 C13 119.9(2) . . ?
C7 C8 C9 118.8(2) . . ?
C8 C13 C14 119.0(2) . . ?
C8 C13 C12 120.7(2) . . ?
C14 C13 C12 120.3(2) . . ?
C14 C5 C4 117.8(2) . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 C14 120.8(2) . . ?
C4 C17 C16 119.0(2) . . ?
C4 C17 C2 107.2(2) . . ?
C16 C17 C2 133.7(2) . . ?
O4 C9 C8 110.79(18) . . ?
O4 C9 C10 106.07(16) . . ?
O4 C9 C18 109.55(18) . . ?
C10 C9 C8 108.34(18) . . ?
C18 C9 C8 109.79(17) . . ?
C18 C9 C10 112.25(19) . . ?
O1 C16 C17 126.4(2) . . ?
O1 C16 C15 117.6(2) . . ?
C17 C16 C15 116.09(19) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 C8 121.5(2) . . ?
C6 C7 H7 119.2 . . ?
O5 C10 C9 111.10(18) . . ?
O5 C10 H10 109.3 . . ?
O5 C10 C11 108.25(19) . . ?
C9 C10 H10 109.3 . . ?
C11 C10 C9 109.71(17) . . ?
C11 C10 H10 109.3 . . ?
C13 C14 C15 122.4(2) . . ?
C5 C14 C13 119.3(2) . . ?
C5 C14 C15 118.3(2) . . ?
C17 C2 C1 127.9(2) . . ?
C3 C2 C17 104.4(2) . . ?
C3 C2 C1 127.6(2) . . ?
C13 C12 H12A 108.3 . . ?
C13 C12 H12B 108.3 . . ?
C13 C12 C11 116.06(19) . . ?
H12A C12 H12B 107.4 . . ?
C11 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
C5 C6 C7 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
O2 C15 C16 115.0(2) . . ?
O2 C15 C14 124.4(2) . . ?
C14 C15 C16 120.6(2) . . ?
O3 C3 H3 124.0 . . ?
C2 C3 O3 112.1(2) . . ?
C2 C3 H3 124.0 . . ?
C10 C11 C12 114.7(2) . . ?
C10 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20171118zzy2-za_0m
_database_code_depnum_ccdc_archive 'CCDC 1825713'
_audit_update_record             
;
2018-02-26 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;
_audit_creation_date             2017-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 O5'
_chemical_formula_sum            'C18 H16 O5'
_chemical_formula_weight         312.31
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   24.2407(8)
_cell_length_b                   9.1871(3)
_cell_length_c                   6.5418(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.441(2)
_cell_angle_gamma                90
_cell_volume                     1404.28(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4908
_cell_measurement_temperature    173
_cell_measurement_theta_max      72.11
_cell_measurement_theta_min      3.78
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    0.897
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1219 before and 0.0657 after correction. The Ratio of minimum to maximum transmission is 0.6261. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.922
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7845
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         63.993
_diffrn_reflns_theta_min         3.783
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.922
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2170
_reflns_number_total             2320
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2320
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+0.2070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0865
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C1(H1)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.49435(8) 0.1519(2) 0.7508(3) 0.0233(5) Uani 1 1 d . . . . .
O3 O 0.54348(8) 0.7223(2) 0.7848(3) 0.0266(5) Uani 1 1 d . . . . .
O2 O 0.62597(8) 0.5231(2) 0.8525(3) 0.0282(5) Uani 1 1 d . . . . .
O5 O 0.26721(9) 0.6312(3) 0.3976(4) 0.0442(6) Uani 1 1 d . . . . .
H5 H 0.2774 0.6232 0.2850 0.066 Uiso 1 1 calc GR . . . .
O4 O 0.33672(9) 0.8219(3) 0.2657(3) 0.0393(6) Uani 1 1 d . . . . .
H4 H 0.3665 0.7726 0.2765 0.059 Uiso 1 1 calc GR . . . .
C7 C 0.46660(11) 0.5493(3) 0.7180(4) 0.0189(6) Uani 1 1 d . . . . .
C14 C 0.36393(12) 0.5969(3) 0.6154(4) 0.0223(6) Uani 1 1 d . . . . .
C5 C 0.57686(11) 0.4803(3) 0.8162(4) 0.0203(6) Uani 1 1 d . . . . .
C8 C 0.42065(11) 0.6520(3) 0.6722(4) 0.0199(6) Uani 1 1 d . . . . .
C16 C 0.39840(11) 0.3478(3) 0.6602(4) 0.0225(6) Uani 1 1 d . . . . .
H16 H 0.3906 0.2464 0.6587 0.027 Uiso 1 1 calc R . . . .
C4 C 0.55924(11) 0.3295(3) 0.8074(4) 0.0203(6) Uani 1 1 d . . . . .
C18 C 0.50235(12) 0.2974(3) 0.7552(4) 0.0195(6) Uani 1 1 d . . . . .
C17 C 0.45446(11) 0.3983(3) 0.7095(4) 0.0183(6) Uani 1 1 d . . . . .
C2 C 0.59000(12) 0.1936(3) 0.8393(4) 0.0238(6) Uani 1 1 d . . . . .
C12 C 0.31214(11) 0.6977(3) 0.5571(5) 0.0275(6) Uani 1 1 d . . . . .
C11 C 0.32781(12) 0.8423(3) 0.4712(5) 0.0285(6) Uani 1 1 d . . . . .
H11 H 0.2946 0.9099 0.4557 0.034 Uiso 1 1 calc R . . . .
C15 C 0.35417(12) 0.4480(3) 0.6133(4) 0.0248(6) Uani 1 1 d . . . . .
H15 H 0.3158 0.4137 0.5785 0.030 Uiso 1 1 calc R . . . .
C6 C 0.52765(12) 0.5958(3) 0.7720(4) 0.0196(6) Uani 1 1 d . . . . .
C9 C 0.43197(12) 0.8135(3) 0.6771(5) 0.0249(7) Uani 1 1 d . . . . .
H9A H 0.4542 0.8358 0.5740 0.030 Uiso 1 1 calc R . . . .
H9B H 0.4561 0.8397 0.8198 0.030 Uiso 1 1 calc R . . . .
C1 C 0.54891(12) 0.0907(3) 0.8020(5) 0.0251(7) Uani 1 1 d . . . . .
H1 H 0.5562 -0.0110 0.8097 0.030 Uiso 1 1 calc R . . . .
C3 C 0.65348(12) 0.1724(4) 0.9015(5) 0.0318(7) Uani 1 1 d . . . . .
H3A H 0.6705 0.2295 0.8072 0.048 Uiso 1 1 calc GR . . . .
H3B H 0.6622 0.0690 0.8897 0.048 Uiso 1 1 calc GR . . . .
H3C H 0.6693 0.2046 1.0482 0.048 Uiso 1 1 calc GR . . . .
C13 C 0.28819(14) 0.7197(5) 0.7475(6) 0.0475(10) Uani 1 1 d . . . . .
H13A H 0.2569 0.7906 0.7118 0.071 Uiso 1 1 calc GR . . . .
H13B H 0.3185 0.7559 0.8676 0.071 Uiso 1 1 calc GR . . . .
H13C H 0.2737 0.6268 0.7858 0.071 Uiso 1 1 calc GR . . . .
C10 C 0.37848(12) 0.9094(4) 0.6265(6) 0.0352(8) Uani 1 1 d . . . . .
H10A H 0.3681 0.9304 0.7599 0.042 Uiso 1 1 calc R . . . .
H10B H 0.3875 1.0032 0.5683 0.042 Uiso 1 1 calc R . . . .


_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 C18 1.350(3) . ?
O1 C1 1.394(3) . ?
O3 C6 1.220(3) . ?
O2 C5 1.216(3) . ?
O5 H5 0.8400 . ?
O5 C12 1.429(4) . ?
O4 H4 0.8400 . ?
O4 C11 1.430(4) . ?
C7 C8 1.429(4) . ?
C7 C17 1.417(4) . ?
C7 C6 1.490(4) . ?
C14 C8 1.419(4) . ?
C14 C12 1.524(4) . ?
C14 C15 1.387(4) . ?
C5 C4 1.446(4) . ?
C5 C6 1.564(4) . ?
C8 C9 1.508(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(4) . ?
C16 C15 1.385(4) . ?
C4 C18 1.362(4) . ?
C4 C2 1.441(4) . ?
C18 C17 1.453(4) . ?
C2 C1 1.348(4) . ?
C2 C3 1.496(4) . ?
C12 C11 1.529(4) . ?
C12 C13 1.521(4) . ?
C11 H11 1.0000 . ?
C11 C10 1.502(4) . ?
C15 H15 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.529(4) . ?
C1 H1 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
C18 O1 C1 105.8(2) . . ?
C12 O5 H5 109.5 . . ?
C11 O4 H4 109.5 . . ?
C8 C7 C6 122.0(2) . . ?
C17 C7 C8 119.8(2) . . ?
C17 C7 C6 118.2(2) . . ?
C8 C14 C12 121.7(3) . . ?
C15 C14 C8 120.3(3) . . ?
C15 C14 C12 118.0(3) . . ?
O2 C5 C4 125.5(2) . . ?
O2 C5 C6 118.4(2) . . ?
C4 C5 C6 116.1(2) . . ?
C7 C8 C9 121.2(2) . . ?
C14 C8 C7 117.8(3) . . ?
C14 C8 C9 121.0(2) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.7(3) . . ?
C18 C4 C5 119.1(2) . . ?
C18 C4 C2 107.4(3) . . ?
C2 C4 C5 133.5(2) . . ?
O1 C18 C4 110.5(2) . . ?
O1 C18 C17 121.6(2) . . ?
C4 C18 C17 127.9(3) . . ?
C7 C17 C18 118.1(2) . . ?
C16 C17 C7 121.1(2) . . ?
C16 C17 C18 120.9(3) . . ?
C4 C2 C3 127.4(3) . . ?
C1 C2 C4 104.6(2) . . ?
C1 C2 C3 127.9(3) . . ?
O5 C12 C14 109.9(2) . . ?
O5 C12 C11 108.6(2) . . ?
O5 C12 C13 105.8(3) . . ?
C14 C12 C11 110.5(2) . . ?
C13 C12 C14 110.2(2) . . ?
C13 C12 C11 111.8(3) . . ?
O4 C11 C12 110.2(2) . . ?
O4 C11 H11 107.8 . . ?
O4 C11 C10 112.9(2) . . ?
C12 C11 H11 107.8 . . ?
C10 C11 C12 110.3(3) . . ?
C10 C11 H11 107.8 . . ?
C14 C15 H15 118.9 . . ?
C16 C15 C14 122.3(3) . . ?
C16 C15 H15 118.9 . . ?
O3 C6 C7 124.3(3) . . ?
O3 C6 C5 115.0(2) . . ?
C7 C6 C5 120.7(2) . . ?
C8 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C8 C9 C10 115.0(2) . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
O1 C1 H1 124.2 . . ?
C2 C1 O1 111.6(2) . . ?
C2 C1 H1 124.2 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C10 C9 113.8(3) . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
