# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_AA436
_database_code_depnum_ccdc_archive 'CCDC 1896414'
loop_
_audit_author_name
_audit_author_address
'Leslaw Sieron'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2019-02-10 deposited with the CCDC.	2019-03-28 downloaded from the CCDC.
;
#===============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
2-((6aS,7S,10aR)-2-methoxy-6-oxo-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-7-yl)acetaldehyde
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 O4'
_chemical_formula_structural     ?
_chemical_formula_sum            'C16 H16 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         272.29


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'

#===============================================================================

#===============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   7.92142(4)
_cell_length_b                   7.19257(4)
_cell_length_c                   11.36141(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.7125(4)
_cell_angle_gamma                90
_cell_volume                     641.465(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    32186
_cell_measurement_theta_min      5.616
_cell_measurement_theta_max      78.962
_cell_special_details            
;
;

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless

_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_min  0.339
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

#===============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_detector_area_resol_mean 5.8140

# number of measured reflections (redundant set)
_diffrn_reflns_number            34348
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0064
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.636
_diffrn_reflns_theta_max         68.116
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
# number of unique reflections
_reflns_number_total             2327
# number of observed reflections (> n sig(I))
_reflns_number_gt                2322
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.982
_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.
;

#===============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+0.1886P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 
;
 Flack x determined using 1046 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2327
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.032

#===============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani -0.00639(18) 0.6010(2) 0.94186(12) 1.000 0.0328(4) d . . .
O2 O Uani 0.03323(13) 0.5221(2) 0.40147(10) 1.000 0.0199(4) d . . .
O3 O Uani -0.11623(14) 0.5648(2) 0.54740(10) 1.000 0.0241(4) d . . .
O4 O Uani 0.64902(14) 0.5279(2) 0.22471(10) 1.000 0.0212(3) d . . .
C1 C Uani -0.0353(2) 0.4555(3) 0.88994(16) 1.000 0.0229(5) d . . .
C2 C Uani 0.0329(2) 0.3987(3) 0.77903(15) 1.000 0.0193(5) d . . .
C3 C Uani 0.15519(19) 0.5375(3) 0.73253(14) 1.000 0.0163(4) d . . .
C4 C Uani 0.3239(2) 0.5389(3) 0.81211(14) 1.000 0.0200(5) d . . .
C5 C Uani 0.4747(2) 0.5425(3) 0.77398(14) 1.000 0.0192(4) d . . .
C6 C Uani 0.49919(19) 0.5519(3) 0.64516(13) 1.000 0.0158(4) d . . .
C7 C Uani 0.33325(19) 0.5974(2) 0.56450(14) 1.000 0.0150(5) d . . .
C8 C Uani 0.1819(2) 0.4908(3) 0.60428(14) 1.000 0.0152(5) d . . .
C9 C Uani 0.02138(19) 0.5290(3) 0.51944(14) 1.000 0.0171(5) d . . .
C10 C Uani 0.1926(2) 0.5126(3) 0.36068(14) 1.000 0.0166(5) d . . .
C11 C Uani 0.3425(2) 0.5542(2) 0.43494(14) 1.000 0.0151(4) d . . .
C12 C Uani 0.4931(2) 0.5557(3) 0.38447(14) 1.000 0.0160(4) d . . .
C13 C Uani 0.4925(2) 0.5204(3) 0.26363(14) 1.000 0.0171(5) d . . .
C14 C Uani 0.3408(2) 0.4777(3) 0.19192(15) 1.000 0.0188(5) d . . .
C15 C Uani 0.1900(2) 0.4733(3) 0.24178(15) 1.000 0.0190(5) d . . .
C16 C Uani 0.6501(2) 0.5176(3) 0.09921(15) 1.000 0.0246(5) d . . .
H1 H Uiso -0.10772 0.36979 0.92249 1.000 0.0270 c RU . .
H2A H Uiso -0.06445 0.37798 0.71609 1.000 0.0230 c RU . .
H2B H Uiso 0.09284 0.27847 0.79377 1.000 0.0230 c RU . .
H3 H Uiso 0.10401 0.66452 0.73334 1.000 0.0200 c RU . .
H4 H Uiso 0.32169 0.53708 0.89550 1.000 0.0240 c RU . .
H5 H Uiso 0.57346 0.53881 0.83154 1.000 0.0230 c RU . .
H6A H Uiso 0.54340 0.43108 0.62089 1.000 0.0190 c RU . .
H6B H Uiso 0.58520 0.64830 0.63481 1.000 0.0190 c RU . .
H7 H Uiso 0.31070 0.73353 0.57144 1.000 0.0180 c RU . .
H8 H Uiso 0.20720 0.35490 0.60064 1.000 0.0180 c RU . .
H12 H Uiso 0.59785 0.58114 0.43296 1.000 0.0190 c RU . .
H14 H Uiso 0.34044 0.45182 0.10989 1.000 0.0230 c RU . .
H15 H Uiso 0.08562 0.44349 0.19412 1.000 0.0230 c RU . .
H16A H Uiso 0.60703 0.39590 0.07023 1.000 0.0370 c RU . .
H16B H Uiso 0.76674 0.53405 0.08125 1.000 0.0370 c RU . .
H16C H Uiso 0.57715 0.61569 0.06006 1.000 0.0370 c RU . .


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.208(3)
O2 C9 1.3570(19)
O2 C10 1.4036(19)
O3 C9 1.2035(19)
O4 C13 1.372(2)
O4 C16 1.429(2)
C1 C2 1.493(2)
C2 C3 1.534(3)
C3 C4 1.510(2)
C3 C8 1.537(2)
C4 C5 1.325(2)
C5 C6 1.504(2)
C6 C7 1.533(2)
C7 C8 1.541(2)
C7 C11 1.516(2)
C8 C9 1.514(2)
C10 C11 1.394(2)
C10 C15 1.378(2)
C11 C12 1.391(2)
C12 C13 1.396(2)
C13 C14 1.393(2)
C14 C15 1.389(2)
C1 H1 0.9500
C2 H2A 0.9900
C2 H2B 0.9900
C3 H3 1.0000
C4 H4 0.9500
C5 H5 0.9500
C6 H6A 0.9900
C6 H6B 0.9900
C7 H7 1.0000
C8 H8 1.0000
C12 H12 0.9500
C14 H14 0.9500
C15 H15 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 O2 C10 120.82(12)
C13 O4 C16 116.50(12)
O1 C1 C2 125.65(18)
C1 C2 C3 115.43(17)
C2 C3 C4 110.33(15)
C2 C3 C8 110.97(16)
C4 C3 C8 110.23(13)
C3 C4 C5 124.68(15)
C4 C5 C6 124.00(15)
C5 C6 C7 112.28(13)
C6 C7 C8 110.90(13)
C6 C7 C11 112.79(13)
C8 C7 C11 108.89(13)
C3 C8 C7 112.38(14)
C3 C8 C9 110.68(13)
C7 C8 C9 110.06(14)
O2 C9 O3 116.98(14)
O2 C9 C8 117.30(13)
O3 C9 C8 125.72(14)
O2 C10 C11 121.38(14)
O2 C10 C15 115.98(14)
C11 C10 C15 122.49(15)
C7 C11 C10 118.92(14)
C7 C11 C12 123.68(14)
C10 C11 C12 117.40(14)
C11 C12 C13 120.94(15)
O4 C13 C12 115.21(14)
O4 C13 C14 124.49(14)
C12 C13 C14 120.29(15)
C13 C14 C15 119.22(15)
C10 C15 C14 119.64(15)
O1 C1 H1 117.00
C2 C1 H1 117.00
C1 C2 H2A 108.00
C1 C2 H2B 108.00
C3 C2 H2A 108.00
C3 C2 H2B 108.00
H2A C2 H2B 107.00
C2 C3 H3 108.00
C4 C3 H3 108.00
C8 C3 H3 108.00
C3 C4 H4 118.00
C5 C4 H4 118.00
C4 C5 H5 118.00
C6 C5 H5 118.00
C5 C6 H6A 109.00
C5 C6 H6B 109.00
C7 C6 H6A 109.00
C7 C6 H6B 109.00
H6A C6 H6B 108.00
C6 C7 H7 108.00
C8 C7 H7 108.00
C11 C7 H7 108.00
C3 C8 H8 108.00
C7 C8 H8 108.00
C9 C8 H8 108.00
C11 C12 H12 120.00
C13 C12 H12 120.00
C13 C14 H14 120.00
C15 C14 H14 120.00
C10 C15 H15 120.00
C14 C15 H15 120.00
O4 C16 H16A 109.00
O4 C16 H16B 109.00
O4 C16 H16C 109.00
H16A C16 H16B 109.00
H16A C16 H16C 109.00
H16B C16 H16C 109.00

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
C10 O2 C9 O3 169.20(18)
C10 O2 C9 C8 -10.9(3)
C9 O2 C10 C11 -15.6(3)
C9 O2 C10 C15 168.96(19)
C16 O4 C13 C12 -171.76(18)
C16 O4 C13 C14 9.5(3)
O1 C1 C2 C3 2.5(3)
C1 C2 C3 C4 71.8(2)
C1 C2 C3 C8 -165.77(15)
C2 C3 C4 C5 137.3(2)
C8 C3 C4 C5 14.4(3)
C2 C3 C8 C7 -166.90(14)
C2 C3 C8 C9 69.6(2)
C4 C3 C8 C7 -44.4(2)
C4 C3 C8 C9 -167.86(17)
C3 C4 C5 C6 2.0(4)
C4 C5 C6 C7 11.9(3)
C5 C6 C7 C8 -41.2(2)
C5 C6 C7 C11 -163.65(15)
C6 C7 C8 C3 59.41(19)
C6 C7 C8 C9 -176.76(15)
C11 C7 C8 C3 -175.92(14)
C11 C7 C8 C9 -52.09(18)
C6 C7 C11 C10 153.31(16)
C6 C7 C11 C12 -27.5(2)
C8 C7 C11 C10 29.8(2)
C8 C7 C11 C12 -151.06(17)
C3 C8 C9 O2 169.99(17)
C3 C8 C9 O3 -10.1(3)
C7 C8 C9 O2 45.2(2)
C7 C8 C9 O3 -134.9(2)
O2 C10 C11 C7 4.3(3)
O2 C10 C11 C12 -174.93(17)
C15 C10 C11 C7 179.47(18)
C15 C10 C11 C12 0.2(3)
O2 C10 C15 C14 174.28(19)
C11 C10 C15 C14 -1.1(3)
C7 C11 C12 C13 -177.95(17)
C10 C11 C12 C13 1.2(3)
C11 C12 C13 O4 179.35(17)
C11 C12 C13 C14 -1.8(3)
O4 C13 C14 C15 179.61(19)
C12 C13 C14 C15 0.9(3)
C13 C14 C15 C10 0.5(3)

####################################################################### 
# 
# 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_AK41
_database_code_depnum_ccdc_archive 'CCDC 1902497'
loop_
_audit_author_name
_audit_author_address
'Leslaw Sieron'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2019-03-11 deposited with the CCDC.	2019-03-28 downloaded from the CCDC.
;
#===============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
2-((6aR,7R,10aS)-2-Methyl-6-oxo-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-7-yl)acetaldehyde
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 O3'
_chemical_formula_structural     ?
_chemical_formula_sum            'C16 H16 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         256.29

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'

#===============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   8.5399(1)
_cell_length_b                   7.2817(1)
_cell_length_c                   10.6201(1)
_cell_angle_alpha                90
_cell_angle_beta                 105.546(1)
_cell_angle_gamma                90
_cell_volume                     636.250(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    15038
_cell_measurement_theta_min      4.303
_cell_measurement_theta_max      78.893
_cell_special_details            
;
;

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless

_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.26
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_min  0.408
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

#===============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_detector_area_resol_mean 5.8140

# number of measured reflections (redundant set)
_diffrn_reflns_number            15530
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0076
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.32
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
# number of unique reflections
_reflns_number_total             2246
# number of observed reflections (> n sig(I))
_reflns_number_gt                2241
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995
_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.
;

#===============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0269P)²+0.1418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'shelxl-2018/3 (sheldrick 2018)'
_refine_ls_extinction_coef       0.029(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1020 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2246
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0556
_refine_ls_wR_factor_gt          0.0556
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.026

#===============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.82302(16) 0.71976(19) 0.67265(14) 1.000 0.0332(4) d . . .
O2 O Uani 0.69339(14) 0.66669(16) 0.21030(11) 1.000 0.0205(3) d . . .
O3 O Uani 0.90368(13) 0.51256(18) 0.32601(11) 1.000 0.0238(3) d . . .
C1 C Uani 0.9322(2) 0.6157(3) 0.67270(16) 1.000 0.0235(5) d . . .
C2 C Uani 0.9129(2) 0.4354(2) 0.60265(16) 1.000 0.0201(5) d . . .
C3 C Uani 0.73909(19) 0.3902(2) 0.52308(15) 1.000 0.0180(5) d . . .
C4 C Uani 0.7280(2) 0.1928(2) 0.47651(16) 1.000 0.0198(5) d . . .
C5 C Uani 0.63342(19) 0.1366(2) 0.36272(16) 1.000 0.0206(5) d . . .
C6 C Uani 0.5239(2) 0.2617(2) 0.26507(16) 1.000 0.0197(5) d . . .
C7 C Uani 0.4991(2) 0.4461(2) 0.32744(15) 1.000 0.0173(5) d . . .
C8 C Uani 0.66400(19) 0.5217(2) 0.40976(16) 1.000 0.0174(4) d . . .
C9 C Uani 0.7669(2) 0.5605(2) 0.31709(16) 1.000 0.0184(5) d . . .
C10 C Uani 0.5249(2) 0.6975(2) 0.17636(16) 1.000 0.0185(4) d . . .
C11 C Uani 0.4225(2) 0.5888(2) 0.22711(15) 1.000 0.0179(4) d . . .
C12 C Uani 0.2558(2) 0.6209(2) 0.18326(15) 1.000 0.0193(4) d . . .
C13 C Uani 0.1919(2) 0.7579(2) 0.09149(16) 1.000 0.0208(5) d . . .
C14 C Uani 0.2999(2) 0.8635(2) 0.04385(16) 1.000 0.0229(5) d . . .
C15 C Uani 0.4663(2) 0.8345(2) 0.08580(17) 1.000 0.0222(5) d . . .
C16 C Uani 0.0112(2) 0.7915(3) 0.04533(17) 1.000 0.0251(5) d . . .
H1 H Uiso 1.03870 0.65050 0.72075 1.000 0.0280 c RU . .
H2 H Uiso 0.64284 0.64138 0.44839 1.000 0.0210 c RU . .
H2A H Uiso 0.98430 0.43472 0.54299 1.000 0.0240 c RU . .
H2B H Uiso 0.95095 0.33670 0.66782 1.000 0.0240 c RU . .
H3 H Uiso 0.66970 0.39905 0.58520 1.000 0.0220 c RU . .
H4 H Uiso 0.79276 0.10371 0.53235 1.000 0.0240 c RU . .
H5 H Uiso 0.63495 0.00990 0.34163 1.000 0.0250 c RU . .
H6A H Uiso 0.57201 0.28405 0.19139 1.000 0.0240 c RU . .
H6B H Uiso 0.41720 0.20142 0.22981 1.000 0.0240 c RU . .
H7 H Uiso 0.42685 0.42588 0.38630 1.000 0.0210 c RU . .
H12 H Uiso 0.18375 0.54785 0.21652 1.000 0.0230 c RU . .
H14 H Uiso 0.25854 0.95717 -0.01850 1.000 0.0280 c RU . .
H15 H Uiso 0.53878 0.90746 0.05292 1.000 0.0270 c RU . .
H16A H Uiso -0.01213 0.91868 0.06442 1.000 0.0380 c RU . .
H16B H Uiso -0.04511 0.70762 0.09067 1.000 0.0380 c RU . .
H16C H Uiso -0.02646 0.76998 -0.04908 1.000 0.0380 c RU . .


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.201(2)
O2 C9 1.377(2)
O2 C10 1.405(2)
O3 C9 1.198(2)
C1 C2 1.496(3)
C2 C3 1.534(2)
C3 C4 1.515(2)
C3 C8 1.537(2)
C4 C5 1.326(2)
C5 C6 1.503(2)
C6 C7 1.537(2)
C7 C8 1.546(2)
C7 C11 1.506(2)
C8 C9 1.511(2)
C10 C11 1.391(2)
C10 C15 1.383(2)
C11 C12 1.394(2)
C12 C13 1.399(2)
C13 C14 1.396(2)
C13 C16 1.509(2)
C14 C15 1.387(2)
C1 H1 0.9500
C2 H2A 0.9900
C2 H2B 0.9900
C3 H3 1.0000
C4 H4 0.9500
C5 H5 0.9500
C6 H6A 0.9900
C6 H6B 0.9900
C7 H7 1.0000
C8 H2 1.0000
C12 H12 0.9500
C14 H14 0.9500
C15 H15 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 O2 C10 120.70(13)
O1 C1 C2 124.83(17)
C1 C2 C3 115.06(14)
C2 C3 C4 110.49(13)
C2 C3 C8 115.89(13)
C4 C3 C8 111.04(13)
C3 C4 C5 124.06(14)
C4 C5 C6 123.80(14)
C5 C6 C7 111.36(13)
C6 C7 C8 110.18(14)
C6 C7 C11 112.44(13)
C8 C7 C11 108.14(12)
C3 C8 C7 110.28(12)
C3 C8 C9 115.65(14)
C7 C8 C9 107.38(13)
O2 C9 O3 116.63(15)
O2 C9 C8 115.15(14)
O3 C9 C8 128.22(15)
O2 C10 C11 121.13(14)
O2 C10 C15 116.65(15)
C11 C10 C15 122.15(16)
C7 C11 C10 117.89(15)
C7 C11 C12 124.26(15)
C10 C11 C12 117.84(14)
C11 C12 C13 121.67(15)
C12 C13 C14 118.23(16)
C12 C13 C16 121.06(15)
C14 C13 C16 120.71(15)
C13 C14 C15 121.30(15)
C10 C15 C14 118.81(15)
O1 C1 H1 118.00
C2 C1 H1 118.00
C1 C2 H2A 109.00
C1 C2 H2B 109.00
C3 C2 H2A 109.00
C3 C2 H2B 108.00
H2A C2 H2B 107.00
C2 C3 H3 106.00
C4 C3 H3 106.00
C8 C3 H3 106.00
C3 C4 H4 118.00
C5 C4 H4 118.00
C4 C5 H5 118.00
C6 C5 H5 118.00
C5 C6 H6A 109.00
C5 C6 H6B 109.00
C7 C6 H6A 109.00
C7 C6 H6B 109.00
H6A C6 H6B 108.00
C6 C7 H7 109.00
C8 C7 H7 109.00
C11 C7 H7 109.00
C3 C8 H2 108.00
C7 C8 H2 108.00
C9 C8 H2 108.00
C11 C12 H12 119.00
C13 C12 H12 119.00
C13 C14 H14 119.00
C15 C14 H14 119.00
C10 C15 H15 121.00
C14 C15 H15 121.00
C13 C16 H16A 109.00
C13 C16 H16B 109.00
C13 C16 H16C 109.00
H16A C16 H16B 109.00
H16A C16 H16C 109.00
H16B C16 H16C 109.00

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
C10 O2 C9 O3 166.65(14)
C10 O2 C9 C8 -14.23(19)
C9 O2 C10 C11 -16.0(2)
C9 O2 C10 C15 167.01(14)
O1 C1 C2 C3 2.0(3)
C1 C2 C3 C4 -170.00(14)
C1 C2 C3 C8 62.60(19)
C4 C3 C8 C7 45.41(18)
C4 C3 C8 C9 -76.65(17)
C2 C3 C8 C7 172.54(13)
C2 C3 C4 C5 -144.99(17)
C8 C3 C4 C5 -15.0(2)
C2 C3 C8 C9 50.48(18)
C3 C4 C5 C6 -0.3(3)
C4 C5 C6 C7 -15.8(2)
C5 C6 C7 C11 167.01(14)
C5 C6 C7 C8 46.30(18)
C6 C7 C8 C9 64.07(15)
C11 C7 C8 C3 174.00(13)
C11 C7 C8 C9 -59.19(16)
C6 C7 C11 C10 -88.46(18)
C6 C7 C8 C3 -62.75(16)
C6 C7 C11 C12 92.55(19)
C8 C7 C11 C10 33.41(19)
C8 C7 C11 C12 -145.57(15)
C3 C8 C9 O3 -5.9(2)
C7 C8 C9 O2 51.50(16)
C7 C8 C9 O3 -129.50(17)
C3 C8 C9 O2 175.09(13)
O2 C10 C11 C7 4.5(2)
O2 C10 C11 C12 -176.44(14)
C15 C10 C11 C7 -178.70(14)
C15 C10 C11 C12 0.4(2)
O2 C10 C15 C14 176.57(14)
C11 C10 C15 C14 -0.4(2)
C7 C11 C12 C13 178.80(14)
C10 C11 C12 C13 -0.2(2)
C11 C12 C13 C14 0.0(2)
C11 C12 C13 C16 -179.77(15)
C12 C13 C14 C15 0.0(2)
C16 C13 C14 C15 179.77(16)
C13 C14 C15 C10 0.2(2)

