# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_YYL-749
_database_code_depnum_ccdc_archive 'CCDC 2180388'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
(R)-4-(naphthalen-2-yloxy)-2-phenyl-4,5,6,7-tetrahydrobenzofuran
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 O2'
_chemical_formula_sum            'C24 H20 O2'
_chemical_formula_weight         340.40

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

_cell_length_a                   5.4569(3)
_cell_length_b                   10.2136(4)
_cell_length_c                   32.074(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1787.62(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9217
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      68.2

_exptl_crystal_description       'thick stick'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.622
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_process_details   'Reqab (Higashi-Rigaku, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rigaku Rotating Anode'
_diffrn_radiation_monochromator  'Osmic Confocal CMF mirrors'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Rigaku Rapid2 curved IP'
_diffrn_measurement_device       
;
Crystal Goniometer Chi-partial
;
_diffrn_measurement_device_type  
;
Rigaku mm007HF microfocus
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            16889
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.755
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3270
_reflns_number_gt                2381
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.998

_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0340P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 772 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3265
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.001
_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 0.4245(3) 0.47362(15) 0.37182(4) 0.0620(5) Uani 1 1 d . . . . .
C1 C 0.5445(5) 0.3901(2) 0.40211(6) 0.0532(6) Uani 1 1 d . . . . .
H1 H 0.722641 0.400875 0.400286 0.064 Uiso 1 1 calc R U . . .
C2 C 0.4557(4) 0.4342(2) 0.44377(6) 0.0503(6) Uani 1 1 d . . . . .
O2 O 0.2223(3) 0.43024(14) 0.50115(4) 0.0534(4) Uani 1 1 d . . . . .
C9 C 0.3617(4) 0.6153(2) 0.54206(6) 0.0475(6) Uani 1 1 d . . . . .
C8 C 0.3806(4) 0.5356(2) 0.50438(6) 0.0480(5) Uani 1 1 d . . . . .
C7 C 0.5229(4) 0.5419(2) 0.46996(7) 0.0531(6) Uani 1 1 d . . . . .
H7 H 0.642094 0.604562 0.464326 0.064 Uiso 1 1 calc R U . . .
C6 C 0.4762(5) 0.2469(2) 0.39579(7) 0.0635(7) Uani 1 1 d . . . . .
H6A H 0.506295 0.223088 0.366973 0.076 Uiso 1 1 calc R U . . .
H6B H 0.580499 0.192860 0.413201 0.076 Uiso 1 1 calc R U . . .
C5 C 0.2101(5) 0.2190(3) 0.40630(7) 0.0686(8) Uani 1 1 d . . . . .
H5A H 0.175071 0.127687 0.400496 0.082 Uiso 1 1 calc R U . . .
H5B H 0.105696 0.271830 0.388531 0.082 Uiso 1 1 calc R U . . .
C4 C 0.1493(5) 0.2479(3) 0.45187(6) 0.0660(7) Uani 1 1 d . . . . .
H4A H -0.026432 0.257362 0.455297 0.079 Uiso 1 1 calc R U . . .
H4B H 0.204396 0.176436 0.469429 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2741(5) 0.3703(2) 0.46395(6) 0.0525(6) Uani 1 1 d . . . . .
C10 C 0.5414(5) 0.7071(2) 0.55090(7) 0.0580(6) Uani 1 1 d . . . . .
H10 H 0.672598 0.717375 0.532675 0.070 Uiso 1 1 calc R U . . .
C11 C 0.5288(5) 0.7837(2) 0.58632(7) 0.0624(7) Uani 1 1 d . . . . .
H11 H 0.649901 0.845522 0.591629 0.075 Uiso 1 1 calc R U . . .
C12 C 0.3385(5) 0.7685(3) 0.61359(7) 0.0644(7) Uani 1 1 d . . . . .
H12 H 0.330814 0.819339 0.637621 0.077 Uiso 1 1 calc R U . . .
C13 C 0.1583(6) 0.6779(3) 0.60540(7) 0.0659(8) Uani 1 1 d . . . . .
H13 H 0.028673 0.667979 0.623955 0.079 Uiso 1 1 calc R U . . .
C14 C 0.1679(5) 0.6016(2) 0.56991(7) 0.0579(6) Uani 1 1 d . . . . .
H14 H 0.044595 0.541027 0.564610 0.069 Uiso 1 1 calc R U . . .
C15 C 0.5185(4) 0.4822(2) 0.33201(6) 0.0523(6) Uani 1 1 d . . . . .
C16 C 0.3963(5) 0.5728(2) 0.30677(7) 0.0619(7) Uani 1 1 d . . . . .
H16 H 0.266337 0.620964 0.317579 0.074 Uiso 1 1 calc R U . . .
C17 C 0.4665(6) 0.5909(3) 0.26665(7) 0.0724(8) Uani 1 1 d . . . . .
H17 H 0.384226 0.651976 0.250335 0.087 Uiso 1 1 calc R U . . .
C18 C 0.6615(6) 0.5191(3) 0.24910(7) 0.0620(7) Uani 1 1 d . . . . .
C19 C 0.7875(5) 0.4299(2) 0.27464(7) 0.0540(6) Uani 1 1 d . . . . .
C20 C 0.7119(5) 0.4131(2) 0.31662(7) 0.0569(6) Uani 1 1 d . . . . .
H20 H 0.794882 0.354498 0.333749 0.068 Uiso 1 1 calc R U . . .
C21 C 0.9837(5) 0.3583(3) 0.25730(7) 0.0696(8) Uani 1 1 d . . . . .
H21 H 1.069228 0.299224 0.273903 0.083 Uiso 1 1 calc R U . . .
C22 C 1.0498(6) 0.3740(3) 0.21675(8) 0.0835(9) Uani 1 1 d . . . . .
H22 H 1.179780 0.325946 0.205914 0.100 Uiso 1 1 calc R U . . .
C23 C 0.9244(7) 0.4615(3) 0.19146(9) 0.0943(11) Uani 1 1 d . . . . .
H23 H 0.970090 0.471321 0.163695 0.113 Uiso 1 1 calc R U . . .
C24 C 0.7362(7) 0.5327(3) 0.20693(8) 0.0888(10) Uani 1 1 d . . . . .
H4 H 0.654476 0.591483 0.189683 0.107 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 C15 1.379(2) . ?
O1 C1 1.449(2) . ?
C1 C2 1.491(3) . ?
C1 C6 1.523(3) . ?
C2 C3 1.351(3) . ?
C2 C7 1.432(3) . ?
O2 C3 1.370(2) . ?
O2 C8 1.383(2) . ?
C9 C10 1.387(3) . ?
C9 C14 1.391(3) . ?
C9 C8 1.461(3) . ?
C8 C7 1.351(3) . ?
C6 C5 1.517(3) . ?
C5 C4 1.528(3) . ?
C4 C3 1.475(3) . ?
C10 C11 1.381(3) . ?
C11 C12 1.367(3) . ?
C12 C13 1.376(4) . ?
C13 C14 1.380(3) . ?
C15 C20 1.362(3) . ?
C15 C16 1.399(3) . ?
C16 C17 1.355(3) . ?
C17 C18 1.410(3) . ?
C18 C19 1.405(3) . ?
C18 C24 1.419(3) . ?
C19 C21 1.411(3) . ?
C19 C20 1.419(3) . ?
C21 C22 1.359(3) . ?
C22 C23 1.388(4) . ?
C23 C24 1.353(4) . ?

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
C15 O1 C1 119.34(18) . . ?
O1 C1 C2 106.05(18) . . ?
O1 C1 C6 111.41(19) . . ?
C2 C1 C6 109.24(19) . . ?
C3 C2 C7 106.1(2) . . ?
C3 C2 C1 121.5(2) . . ?
C7 C2 C1 132.4(2) . . ?
C3 O2 C8 106.48(17) . . ?
C10 C9 C14 118.3(2) . . ?
C10 C9 C8 119.8(2) . . ?
C14 C9 C8 121.9(2) . . ?
C7 C8 O2 109.57(19) . . ?
C7 C8 C9 133.6(2) . . ?
O2 C8 C9 116.83(19) . . ?
C8 C7 C2 107.2(2) . . ?
C5 C6 C1 112.7(2) . . ?
C6 C5 C4 112.6(2) . . ?
C3 C4 C5 108.4(2) . . ?
C2 C3 O2 110.6(2) . . ?
C2 C3 C4 128.4(2) . . ?
O2 C3 C4 120.8(2) . . ?
C11 C10 C9 121.1(2) . . ?
C12 C11 C10 120.0(3) . . ?
C11 C12 C13 119.8(2) . . ?
C12 C13 C14 120.7(3) . . ?
C13 C14 C9 120.1(3) . . ?
C20 C15 O1 126.2(2) . . ?
C20 C15 C16 120.2(2) . . ?
O1 C15 C16 113.6(2) . . ?
C17 C16 C15 120.3(2) . . ?
C16 C17 C18 121.5(2) . . ?
C19 C18 C17 118.3(2) . . ?
C19 C18 C24 118.6(3) . . ?
C17 C18 C24 123.1(3) . . ?
C18 C19 C21 118.6(2) . . ?
C18 C19 C20 119.3(2) . . ?
C21 C19 C20 122.2(2) . . ?
C15 C20 C19 120.4(2) . . ?
C22 C21 C19 121.1(3) . . ?
C21 C22 C23 120.3(3) . . ?
C24 C23 C22 120.4(3) . . ?
C23 C24 C18 121.0(3) . . ?

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
C15 O1 C1 C2 161.92(19) . . . . ?
C15 O1 C1 C6 -79.3(3) . . . . ?
O1 C1 C2 C3 99.1(2) . . . . ?
C6 C1 C2 C3 -21.1(3) . . . . ?
O1 C1 C2 C7 -79.5(3) . . . . ?
C6 C1 C2 C7 160.3(2) . . . . ?
C3 O2 C8 C7 1.0(2) . . . . ?
C3 O2 C8 C9 -179.59(18) . . . . ?
C10 C9 C8 C7 -12.3(4) . . . . ?
C14 C9 C8 C7 168.1(2) . . . . ?
C10 C9 C8 O2 168.46(19) . . . . ?
C14 C9 C8 O2 -11.1(3) . . . . ?
O2 C8 C7 C2 -1.1(2) . . . . ?
C9 C8 C7 C2 179.6(2) . . . . ?
C3 C2 C7 C8 0.8(3) . . . . ?
C1 C2 C7 C8 179.5(2) . . . . ?
O1 C1 C6 C5 -68.6(3) . . . . ?
C2 C1 C6 C5 48.2(3) . . . . ?
C1 C6 C5 C4 -61.4(3) . . . . ?
C6 C5 C4 C3 40.8(3) . . . . ?
C7 C2 C3 O2 -0.1(2) . . . . ?
C1 C2 C3 O2 -179.03(19) . . . . ?
C7 C2 C3 C4 -176.0(2) . . . . ?
C1 C2 C3 C4 5.1(4) . . . . ?
C8 O2 C3 C2 -0.5(2) . . . . ?
C8 O2 C3 C4 175.7(2) . . . . ?
C5 C4 C3 C2 -14.5(3) . . . . ?
C5 C4 C3 O2 170.0(2) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?
C8 C9 C10 C11 -179.8(2) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 C9 0.3(3) . . . . ?
C10 C9 C14 C13 -0.3(3) . . . . ?
C8 C9 C14 C13 179.3(2) . . . . ?
C1 O1 C15 C20 3.8(3) . . . . ?
C1 O1 C15 C16 -175.7(2) . . . . ?
C20 C15 C16 C17 1.2(4) . . . . ?
O1 C15 C16 C17 -179.3(2) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -1.7(4) . . . . ?
C16 C17 C18 C24 178.3(3) . . . . ?
C17 C18 C19 C21 -179.7(2) . . . . ?
C24 C18 C19 C21 0.3(4) . . . . ?
C17 C18 C19 C20 1.3(4) . . . . ?
C24 C18 C19 C20 -178.7(2) . . . . ?
O1 C15 C20 C19 179.0(2) . . . . ?
C16 C15 C20 C19 -1.6(3) . . . . ?
C18 C19 C20 C15 0.3(4) . . . . ?
C21 C19 C20 C15 -178.7(2) . . . . ?
C18 C19 C21 C22 -0.3(4) . . . . ?
C20 C19 C21 C22 178.7(3) . . . . ?
C19 C21 C22 C23 0.0(4) . . . . ?
C21 C22 C23 C24 0.5(5) . . . . ?
C22 C23 C24 C18 -0.5(5) . . . . ?
C19 C18 C24 C23 0.1(4) . . . . ?
C17 C18 C24 C23 -180.0(3) . . . . ?

_refine_diff_density_max         0.106
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.029

####################################################################### 
# 
# 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_ZZH1399-OAdd
_database_code_depnum_ccdc_archive 'CCDC 2180389'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
'(S)-4-(naphthalen-2-yloxy)-2-phenyl-4,5,6,7-tetrahydrobenzofuran'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 O2'
_chemical_formula_sum            'C24 H20 O2'
_chemical_formula_weight         340.40

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

_cell_length_a                   5.4563(3)
_cell_length_b                   10.2121(6)
_cell_length_c                   32.052(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1785.94(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6974
_cell_measurement_theta_min      6.9
_cell_measurement_theta_max      71.2

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.622
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_process_details   'Reqab (Rigaku, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  'OSMIC CMF optics'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Rigaku Rapid2 curved large area IP'
_diffrn_measurement_device       
;
Crystal Goniometer chi-partial
;
_diffrn_measurement_device_type  
;
Rigaku MM007HF Spider
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            36229
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.1106
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         7.024
_diffrn_reflns_theta_max         72.108
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3502
_reflns_number_gt                2858
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.999

_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0354P)²+0.0685P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0163(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 955 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3500
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.001
_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 0.7775(3) 0.56977(16) 0.49882(4) 0.0499(4) Uani 1 1 d . . . . .
C1' C 0.2881(5) 0.5872(3) 0.68326(7) 0.0530(7) Uani 1 1 d . . . . .
H1' H 0.205665 0.646102 0.666146 0.064 Uiso 1 1 calc R U . . .
C2 C 0.6201(4) 0.4647(2) 0.49571(7) 0.0452(6) Uani 1 1 d . . . . .
O2 O 0.5758(3) 0.52617(17) 0.62819(5) 0.0582(5) Uani 1 1 d . . . . .
C2' C 0.4810(5) 0.5178(2) 0.66794(7) 0.0493(6) Uani 1 1 d . . . . .
C3 C 0.4764(5) 0.4584(2) 0.53013(7) 0.0497(6) Uani 1 1 d . . . . .
H3 H 0.356556 0.396092 0.535758 0.060 Uiso 1 1 calc R U . . .
C3' C 0.6041(5) 0.4269(3) 0.69318(8) 0.0590(7) Uani 1 1 d . . . . .
H3' H 0.734461 0.379014 0.682359 0.071 Uiso 1 1 calc R U . . .
C5' C 0.2624(8) 0.4671(4) 0.79307(9) 0.0872(11) Uani 1 1 d . . . . .
H5' H 0.342921 0.407847 0.810311 0.105 Uiso 1 1 calc R U . . .
C5 C 0.5228(5) 0.7532(3) 0.60411(8) 0.0612(8) Uani 1 1 d . . . . .
H5A H 0.418591 0.806999 0.586572 0.073 Uiso 1 1 calc R U . . .
H5AB H 0.492125 0.777392 0.632905 0.073 Uiso 1 1 calc R U . . .
C4 C 0.4551(5) 0.6100(2) 0.59793(6) 0.0507(6) Uani 1 1 d . . . . .
H4 H 0.276974 0.598993 0.599758 0.061 Uiso 1 1 calc R U . . .
C4' C 0.5335(6) 0.4087(3) 0.73339(8) 0.0706(9) Uani 1 1 d . . . . .
H4' H 0.615480 0.347502 0.749742 0.085 Uiso 1 1 calc R U . . .
C7 C 0.8515(6) 0.7522(3) 0.54808(7) 0.0624(8) Uani 1 1 d . . . . .
H7A H 0.797612 0.823786 0.530443 0.075 Uiso 1 1 calc R U . . .
H7AB H 1.027227 0.742192 0.544809 0.075 Uiso 1 1 calc R U . . .
C6 C 0.7892(6) 0.7812(3) 0.59367(7) 0.0659(8) Uani 1 1 d . . . . .
H6A H 0.893388 0.728499 0.611540 0.079 Uiso 1 1 calc R U . . .
H6AB H 0.824022 0.872568 0.599472 0.079 Uiso 1 1 calc R U . . .
C6' C 0.0759(7) 0.5387(4) 0.80863(10) 0.0912(12) Uani 1 1 d . . . . .
H6' H 0.031842 0.529606 0.836510 0.109 Uiso 1 1 calc R U . . .
C9 C 0.6379(4) 0.3851(2) 0.45785(6) 0.0444(6) Uani 1 1 d . . . . .
C8' C 0.0160(6) 0.6417(3) 0.74257(8) 0.0663(8) Uani 1 1 d . . . . .
H8' H -0.069449 0.700655 0.725927 0.080 Uiso 1 1 calc R U . . .
C7' C -0.0504(7) 0.6256(3) 0.78338(9) 0.0815(10) Uani 1 1 d . . . . .
H7' H -0.180918 0.673251 0.794224 0.098 Uiso 1 1 calc R U . . .
C3A C 0.5446(5) 0.5660(2) 0.55607(7) 0.0479(6) Uani 1 1 d . . . . .
C14 C 0.8324(5) 0.3988(3) 0.43006(7) 0.0537(6) Uani 1 1 d . . . . .
H14 H 0.955504 0.459494 0.435358 0.064 Uiso 1 1 calc R U . . .
C13 C 0.8422(6) 0.3216(3) 0.39441(7) 0.0631(8) Uani 1 1 d . . . . .
H13 H 0.972041 0.331083 0.375861 0.076 Uiso 1 1 calc R U . . .
C12 C 0.6628(6) 0.2319(3) 0.38637(7) 0.0605(7) Uani 1 1 d . . . . .
H12 H 0.670758 0.181055 0.362328 0.073 Uiso 1 1 calc R U . . .
C11 C 0.4704(5) 0.2162(3) 0.41361(7) 0.0599(7) Uani 1 1 d . . . . .
H11 H 0.349329 0.154332 0.408256 0.072 Uiso 1 1 calc R U . . .
C10 C 0.4583(5) 0.2934(3) 0.44910(7) 0.0547(6) Uani 1 1 d . . . . .
H10 H 0.327241 0.283398 0.467376 0.066 Uiso 1 1 calc R U . . .
C7A C 0.7259(5) 0.6303(3) 0.53599(7) 0.0497(6) Uani 1 1 d . . . . .
C4A C 0.3386(6) 0.4805(3) 0.75078(7) 0.0599(8) Uani 1 1 d . . . . .
C8A C 0.2121(5) 0.5700(3) 0.72540(7) 0.0516(6) Uani 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 C7A 1.371(3) . ?
O1 C2 1.378(3) . ?
C1' C2' 1.361(3) . ?
C1' C8A 1.424(3) . ?
C2 C3 1.355(3) . ?
C2 C9 1.464(3) . ?
O2 C2' 1.378(3) . ?
O2 C4 1.452(3) . ?
C2' C3' 1.403(3) . ?
C3 C3A 1.427(3) . ?
C3' C4' 1.358(3) . ?
C5' C6' 1.348(5) . ?
C5' C4A 1.425(3) . ?
C5 C6 1.519(4) . ?
C5 C4 1.522(4) . ?
C4 C3A 1.497(3) . ?
C4' C4A 1.407(4) . ?
C7 C7A 1.472(3) . ?
C7 C6 1.530(3) . ?
C6' C7' 1.385(5) . ?
C9 C10 1.384(3) . ?
C9 C14 1.392(3) . ?
C8' C7' 1.367(3) . ?
C8' C8A 1.408(4) . ?
C3A C7A 1.351(3) . ?
C14 C13 1.389(3) . ?
C13 C12 1.365(4) . ?
C12 C11 1.375(4) . ?
C11 C10 1.386(3) . ?
C4A C8A 1.405(4) . ?

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
C7A O1 C2 106.62(18) . . ?
C2' C1' C8A 120.2(2) . . ?
C3 C2 O1 109.8(2) . . ?
C3 C2 C9 133.4(2) . . ?
O1 C2 C9 116.80(19) . . ?
C2' O2 C4 118.95(19) . . ?
C1' C2' O2 126.3(2) . . ?
C1' C2' C3' 120.5(2) . . ?
O2 C2' C3' 113.2(2) . . ?
C2 C3 C3A 106.7(2) . . ?
C4' C3' C2' 120.1(3) . . ?
C6' C5' C4A 121.4(3) . . ?
C6 C5 C4 112.6(3) . . ?
O2 C4 C3A 105.9(2) . . ?
O2 C4 C5 111.7(2) . . ?
C3A C4 C5 109.0(2) . . ?
C3' C4' C4A 121.3(3) . . ?
C7A C7 C6 108.2(2) . . ?
C5 C6 C7 112.7(2) . . ?
C5' C6' C7' 120.4(3) . . ?
C10 C9 C14 118.6(2) . . ?
C10 C9 C2 119.8(2) . . ?
C14 C9 C2 121.7(2) . . ?
C7' C8' C8A 120.9(3) . . ?
C8' C7' C6' 120.3(3) . . ?
C7A C3A C3 106.7(2) . . ?
C7A C3A C4 121.3(2) . . ?
C3 C3A C4 131.9(2) . . ?
C13 C14 C9 119.9(3) . . ?
C12 C13 C14 120.6(3) . . ?
C13 C12 C11 120.4(3) . . ?
C12 C11 C10 119.4(3) . . ?
C9 C10 C11 121.2(2) . . ?
C3A C7A O1 110.2(2) . . ?
C3A C7A C7 128.8(2) . . ?
O1 C7A C7 120.9(2) . . ?
C8A C4A C4' 118.8(2) . . ?
C8A C4A C5' 118.0(3) . . ?
C4' C4A C5' 123.2(3) . . ?
C4A C8A C8' 119.0(2) . . ?
C4A C8A C1' 119.1(2) . . ?
C8' C8A C1' 121.9(2) . . ?

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.033


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate'
####################################################################### 
# 
# 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_exp_373_XXXX
_database_code_depnum_ccdc_archive 'CCDC 2180390'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
'(7aS,11aR)-8-oxo-7a-(2-oxo-2-phenylethyl)-7a,8,9,10,11,11a-
hexahydronaphtho[2,1-b]benzofuran-3-carbonitrile'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H19 N O3'
_chemical_formula_sum            'C25 H19 N O3'
_chemical_formula_weight         381.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.1453(3)
_cell_length_b                   13.5230(5)
_cell_length_c                   17.9736(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1979.77(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12803
_cell_measurement_theta_min      3.0130
_cell_measurement_theta_max      25.8470

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.987
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0497
-1 -5 3 0.0555
0 -1 5 0.0935
5 3 2 0.0919
-1 -5 0 0.0751
-4 -5 -1 0.1135
-5 0 -2 0.1216
0 5 2 0.0901
-1 -1 5 0.0695
-1 -5 1 0.0677
0 -1 0 0.0806
-2 14 0 0.0796
0 -1 -5 0.0540
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.148
_exptl_crystal_density_diffrn    1.280
_exptl_absorpt_correction_T_min  0.374
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku mm003 (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Double bounce MaxFlux multilayer optic'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Pro: Kappa single'
_diffrn_detector                 'Dectris Pilatus200K 3R'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            37692
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.721
_diffrn_reflns_theta_max         27.097
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4367
_reflns_number_gt                3905
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0495P)²+0.1256P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1525 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4367
_refine_ls_number_parameters     282
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.180
_refine_ls_shift/su_max          0.001
_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
O2 O 0.37855(15) 0.55195(10) 0.20940(7) 0.0583(3) Uani 1 1 d . . . . .
N1 N 0.3048(3) 0.7026(3) 0.68764(13) 0.1115(9) Uani 1 1 d . . . . .
C1 C 0.5583(2) 0.54102(14) 0.20871(10) 0.0525(4) Uani 1 1 d . . . . .
O3 O 0.87881(17) 0.54461(11) 0.17177(8) 0.0662(4) Uani 1 1 d . . . . .
C2 C 0.6089(3) 0.52941(16) 0.29166(10) 0.0621(5) Uani 1 1 d D . . . .
H2 H 0.710379 0.564912 0.303774 0.075 Uiso 0.671(8) 1 calc R U P A 1
H2B H 0.690629 0.581979 0.297874 0.075 Uiso 0.329(8) 1 calc R U P A 2
O1 O 0.5717(2) 0.46114(11) 0.09154(8) 0.0752(4) Uani 1 1 d . . . . .
C3 C 0.4614(2) 0.57152(12) 0.33018(10) 0.0479(4) Uani 1 1 d . . . . .
C4 C 0.3350(2) 0.57649(13) 0.28034(10) 0.0503(4) Uani 1 1 d . . . . .
C5 C 0.5865(2) 0.45081(14) 0.15759(10) 0.0555(4) Uani 1 1 d . . . . .
C6 C 0.6249(3) 0.35245(15) 0.19125(12) 0.0727(6) Uani 1 1 d D . . . .
H6A H 0.522154 0.317561 0.198764 0.087 Uiso 0.671(8) 1 calc R U P A 1
H6B H 0.688246 0.314833 0.155379 0.087 Uiso 0.671(8) 1 calc R U P A 1
H6C H 0.736859 0.333543 0.179647 0.087 Uiso 0.329(8) 1 calc R U P A 2
H6D H 0.551540 0.302398 0.171505 0.087 Uiso 0.329(8) 1 calc R U P A 2
C8 C 0.6142(7) 0.4146(3) 0.3164(2) 0.0680(12) Uani 0.671(8) 1 d D . P A 1
H8A H 0.660983 0.409676 0.365934 0.082 Uiso 0.671(8) 1 calc R U P A 1
H8B H 0.503103 0.388938 0.318434 0.082 Uiso 0.671(8) 1 calc R U P A 1
C7 C 0.7156(6) 0.3522(2) 0.26263(19) 0.0717(12) Uani 0.671(8) 1 d D . P A 1
H7A H 0.824125 0.380533 0.256173 0.086 Uiso 0.671(8) 1 calc R U P A 1
H7B H 0.727343 0.285266 0.281268 0.086 Uiso 0.671(8) 1 calc R U P A 1
C9 C 0.1750(2) 0.60291(15) 0.30002(11) 0.0600(5) Uani 1 1 d . . . . .
H9 H 0.091301 0.604391 0.264841 0.072 Uiso 1 1 calc R U . . .
C10 C 0.1458(2) 0.62642(15) 0.37253(11) 0.0612(4) Uani 1 1 d . . . . .
H10 H 0.040222 0.644359 0.386858 0.073 Uiso 1 1 calc R U . . .
C11 C 0.2720(2) 0.62426(13) 0.42657(10) 0.0524(4) Uani 1 1 d . . . . .
C12 C 0.4345(2) 0.59560(12) 0.40564(10) 0.0481(4) Uani 1 1 d . . . . .
C13 C 0.5579(2) 0.59281(14) 0.46105(10) 0.0571(4) Uani 1 1 d . . . . .
H13 H 0.664014 0.574232 0.448015 0.069 Uiso 1 1 calc R U . . .
C14 C 0.5245(3) 0.61675(16) 0.53299(11) 0.0644(5) Uani 1 1 d . . . . .
H14 H 0.607132 0.614006 0.568631 0.077 Uiso 1 1 calc R U . . .
C15 C 0.3647(3) 0.64568(15) 0.55345(10) 0.0629(5) Uani 1 1 d . . . . .
C16 C 0.2412(3) 0.64899(14) 0.50165(11) 0.0612(5) Uani 1 1 d . . . . .
H16 H 0.136119 0.667724 0.516106 0.073 Uiso 1 1 calc R U . . .
C17 C 0.3307(3) 0.6753(2) 0.62913(13) 0.0806(7) Uani 1 1 d . . . . .
C18 C 0.6293(2) 0.63356(14) 0.17334(10) 0.0561(4) Uani 1 1 d . . . . .
H18A H 0.570619 0.647746 0.127608 0.067 Uiso 1 1 calc R U . . .
H18B H 0.613949 0.689121 0.206761 0.067 Uiso 1 1 calc R U . . .
C19 C 0.8098(2) 0.62199(14) 0.15647(10) 0.0546(4) Uani 1 1 d . . . . .
C20 C 0.9007(3) 0.70351(15) 0.11931(10) 0.0609(5) Uani 1 1 d . . . . .
C21 C 0.8353(4) 0.79568(17) 0.10924(16) 0.0887(8) Uani 1 1 d . . . . .
H21 H 0.731360 0.809999 0.127796 0.106 Uiso 1 1 calc R U . . .
C22 C 0.9235(6) 0.8684(2) 0.0713(2) 0.1088(11) Uani 1 1 d . . . . .
H22 H 0.877266 0.930627 0.064260 0.131 Uiso 1 1 calc R U . . .
C23 C 1.0742(5) 0.8495(3) 0.04478(16) 0.1020(11) Uani 1 1 d . . . . .
H23 H 1.131176 0.897819 0.018496 0.122 Uiso 1 1 calc R U . . .
C24 C 1.1429(5) 0.7599(3) 0.05649(15) 0.1017(10) Uani 1 1 d . . . . .
H24 H 1.248876 0.747691 0.039573 0.122 Uiso 1 1 calc R U . . .
C25 C 1.0577(3) 0.6859(2) 0.09335(13) 0.0799(6) Uani 1 1 d . . . . .
H25 H 1.106250 0.624388 0.100614 0.096 Uiso 1 1 calc R U . . .
C8B C 0.6971(10) 0.4436(5) 0.3144(4) 0.062(2) Uani 0.329(8) 1 d D . P A 2
H8B1 H 0.696449 0.436545 0.368152 0.075 Uiso 0.329(8) 1 calc R U P A 2
H8B2 H 0.809790 0.445439 0.297047 0.075 Uiso 0.329(8) 1 calc R U P A 2
C7B C 0.6022(11) 0.3615(5) 0.2776(3) 0.068(2) Uani 0.329(8) 1 d D . P A 2
H7C H 0.486441 0.371194 0.287928 0.082 Uiso 0.329(8) 1 calc R U P A 2
H7D H 0.634456 0.299357 0.300184 0.082 Uiso 0.329(8) 1 calc R U P A 2


_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
O2 C4 1.364(2) . ?
O2 C1 1.472(2) . ?
N1 C17 1.134(3) . ?
C1 C18 1.518(3) . ?
C1 C5 1.544(2) . ?
C1 C2 1.555(2) . ?
O3 C19 1.219(2) . ?
C2 C8B 1.425(6) . ?
C2 C3 1.499(3) . ?
C2 C8 1.615(4) . ?
C2 H2 0.9800 . ?
C2 H2B 0.9800 . ?
O1 C5 1.201(2) . ?
C3 C4 1.367(2) . ?
C3 C12 1.412(2) . ?
C4 C9 1.397(3) . ?
C5 C6 1.494(3) . ?
C6 C7 1.481(4) . ?
C6 C7B 1.567(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C6 H6D 0.9700 . ?
C8 C7 1.527(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.362(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.414(3) . ?
C10 H10 0.9300 . ?
C11 C16 1.413(3) . ?
C11 C12 1.430(3) . ?
C12 C13 1.416(3) . ?
C13 C14 1.360(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.408(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(3) . ?
C15 C17 1.445(3) . ?
C16 H16 0.9300 . ?
C18 C19 1.509(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.486(3) . ?
C20 C21 1.368(3) . ?
C20 C25 1.382(3) . ?
C21 C22 1.396(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.342(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.351(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C8B C7B 1.506(8) . ?
C8B H8B1 0.9700 . ?
C8B H8B2 0.9700 . ?
C7B H7C 0.9700 . ?
C7B H7D 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 O2 C1 106.93(13) . . ?
O2 C1 C18 107.44(14) . . ?
O2 C1 C5 103.43(14) . . ?
C18 C1 C5 110.21(15) . . ?
O2 C1 C2 105.42(14) . . ?
C18 C1 C2 112.56(15) . . ?
C5 C1 C2 116.83(15) . . ?
C8B C2 C3 125.5(4) . . ?
C8B C2 C1 119.4(3) . . ?
C3 C2 C1 101.06(14) . . ?
C3 C2 C8 105.0(2) . . ?
C1 C2 C8 111.6(2) . . ?
C3 C2 H2 112.8 . . ?
C1 C2 H2 112.8 . . ?
C8 C2 H2 112.8 . . ?
C8B C2 H2B 102.5 . . ?
C3 C2 H2B 102.5 . . ?
C1 C2 H2B 102.5 . . ?
C4 C3 C12 120.08(16) . . ?
C4 C3 C2 108.67(15) . . ?
C12 C3 C2 130.97(15) . . ?
O2 C4 C3 113.86(15) . . ?
O2 C4 C9 122.79(16) . . ?
C3 C4 C9 123.35(17) . . ?
O1 C5 C6 121.64(17) . . ?
O1 C5 C1 118.75(17) . . ?
C6 C5 C1 119.56(16) . . ?
C7 C6 C5 117.2(2) . . ?
C5 C6 C7B 107.9(3) . . ?
C7 C6 H6A 108.0 . . ?
C5 C6 H6A 108.0 . . ?
C7 C6 H6B 108.0 . . ?
C5 C6 H6B 108.0 . . ?
H6A C6 H6B 107.2 . . ?
C5 C6 H6C 110.1 . . ?
C7B C6 H6C 110.1 . . ?
C5 C6 H6D 110.1 . . ?
C7B C6 H6D 110.1 . . ?
H6C C6 H6D 108.4 . . ?
C7 C8 C2 111.8(3) . . ?
C7 C8 H8A 109.3 . . ?
C2 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C2 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C6 C7 C8 106.1(3) . . ?
C6 C7 H7A 110.5 . . ?
C8 C7 H7A 110.5 . . ?
C6 C7 H7B 110.5 . . ?
C8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C10 C9 C4 117.69(17) . . ?
C10 C9 H9 121.2 . . ?
C4 C9 H9 121.2 . . ?
C9 C10 C11 121.69(17) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C16 C11 C10 121.50(18) . . ?
C16 C11 C12 118.66(18) . . ?
C10 C11 C12 119.84(16) . . ?
C3 C12 C13 124.01(16) . . ?
C3 C12 C11 117.33(15) . . ?
C13 C12 C11 118.66(16) . . ?
C14 C13 C12 121.35(19) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 119.96(18) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.64(17) . . ?
C16 C15 C17 119.3(2) . . ?
C14 C15 C17 120.0(2) . . ?
C15 C16 C11 120.73(19) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N1 C17 C15 177.1(3) . . ?
C19 C18 C1 111.69(15) . . ?
C19 C18 H18A 109.3 . . ?
C1 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C1 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
O3 C19 C20 120.54(17) . . ?
O3 C19 C18 119.52(18) . . ?
C20 C19 C18 119.91(17) . . ?
C21 C20 C25 118.2(2) . . ?
C21 C20 C19 122.8(2) . . ?
C25 C20 C19 119.0(2) . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 120.7(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 119.6(3) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C25 121.0(3) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C20 C25 C24 120.0(3) . . ?
C20 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C2 C8B C7B 102.4(5) . . ?
C2 C8B H8B1 111.3 . . ?
C7B C8B H8B1 111.3 . . ?
C2 C8B H8B2 111.3 . . ?
C7B C8B H8B2 111.3 . . ?
H8B1 C8B H8B2 109.2 . . ?
C8B C7B C6 115.6(6) . . ?
C8B C7B H7C 108.4 . . ?
C6 C7B H7C 108.4 . . ?
C8B C7B H7D 108.4 . . ?
C6 C7B H7D 108.4 . . ?
H7C C7B H7D 107.4 . . ?

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
C4 O2 C1 C18 -102.82(16) . . . . ?
C4 O2 C1 C5 140.60(14) . . . . ?
C4 O2 C1 C2 17.43(19) . . . . ?
O2 C1 C2 C8B 122.4(5) . . . . ?
C18 C1 C2 C8B -120.8(5) . . . . ?
C5 C1 C2 C8B 8.2(5) . . . . ?
O2 C1 C2 C3 -19.73(19) . . . . ?
C18 C1 C2 C3 97.09(18) . . . . ?
C5 C1 C2 C3 -133.91(16) . . . . ?
O2 C1 C2 C8 91.4(2) . . . . ?
C18 C1 C2 C8 -151.7(2) . . . . ?
C5 C1 C2 C8 -22.7(3) . . . . ?
C8B C2 C3 C4 -123.2(4) . . . . ?
C1 C2 C3 C4 15.8(2) . . . . ?
C8 C2 C3 C4 -100.4(2) . . . . ?
C8B C2 C3 C12 50.6(5) . . . . ?
C1 C2 C3 C12 -170.47(17) . . . . ?
C8 C2 C3 C12 73.4(3) . . . . ?
C1 O2 C4 C3 -7.7(2) . . . . ?
C1 O2 C4 C9 173.08(17) . . . . ?
C12 C3 C4 O2 179.56(15) . . . . ?
C2 C3 C4 O2 -5.9(2) . . . . ?
C12 C3 C4 C9 -1.3(3) . . . . ?
C2 C3 C4 C9 173.28(19) . . . . ?
O2 C1 C5 O1 75.4(2) . . . . ?
C18 C1 C5 O1 -39.2(2) . . . . ?
C2 C1 C5 O1 -169.33(19) . . . . ?
O2 C1 C5 C6 -102.2(2) . . . . ?
C18 C1 C5 C6 143.16(18) . . . . ?
C2 C1 C5 C6 13.0(3) . . . . ?
O1 C5 C6 C7 151.7(3) . . . . ?
C1 C5 C6 C7 -30.7(3) . . . . ?
O1 C5 C6 C7B -169.4(4) . . . . ?
C1 C5 C6 C7B 8.2(4) . . . . ?
C3 C2 C8 C7 159.5(4) . . . . ?
C1 C2 C8 C7 50.9(5) . . . . ?
C5 C6 C7 C8 56.2(4) . . . . ?
C2 C8 C7 C6 -66.4(5) . . . . ?
O2 C4 C9 C10 -179.71(17) . . . . ?
C3 C4 C9 C10 1.2(3) . . . . ?
C4 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C16 179.81(19) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C4 C3 C12 C13 -179.85(17) . . . . ?
C2 C3 C12 C13 7.0(3) . . . . ?
C4 C3 C12 C11 0.3(2) . . . . ?
C2 C3 C12 C11 -172.89(18) . . . . ?
C16 C11 C12 C3 -179.88(16) . . . . ?
C10 C11 C12 C3 0.7(2) . . . . ?
C16 C11 C12 C13 0.2(2) . . . . ?
C10 C11 C12 C13 -179.16(17) . . . . ?
C3 C12 C13 C14 -179.92(18) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C13 C14 C15 C17 -177.3(2) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C17 C15 C16 C11 177.51(19) . . . . ?
C10 C11 C16 C15 179.43(18) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
O2 C1 C18 C19 -169.11(14) . . . . ?
C5 C1 C18 C19 -57.07(18) . . . . ?
C2 C1 C18 C19 75.28(18) . . . . ?
C1 C18 C19 O3 -0.1(2) . . . . ?
C1 C18 C19 C20 177.95(15) . . . . ?
O3 C19 C20 C21 -171.7(2) . . . . ?
C18 C19 C20 C21 10.2(3) . . . . ?
O3 C19 C20 C25 8.6(3) . . . . ?
C18 C19 C20 C25 -169.47(17) . . . . ?
C25 C20 C21 C22 2.3(4) . . . . ?
C19 C20 C21 C22 -177.4(2) . . . . ?
C20 C21 C22 C23 -0.7(5) . . . . ?
C21 C22 C23 C24 -1.6(5) . . . . ?
C22 C23 C24 C25 2.2(4) . . . . ?
C21 C20 C25 C24 -1.7(3) . . . . ?
C19 C20 C25 C24 178.0(2) . . . . ?
C23 C24 C25 C20 -0.6(4) . . . . ?
C3 C2 C8B C7B 86.2(6) . . . . ?
C1 C2 C8B C7B -46.1(7) . . . . ?
C2 C8B C7B C6 73.2(8) . . . . ?
C5 C6 C7B C8B -54.1(7) . . . . ?

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
_geom_hbond_publ_flag
C6 H6A N1 0.97 2.68 3.579(4) 153.5 2_564 yes
C9 H9 O3 0.93 2.54 3.429(2) 160.2 1_455 yes

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.023

