# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_d24673
_database_code_depnum_ccdc_archive 'CCDC 2290696'
loop_
_audit_author_name
_audit_author_address
'Jivan Shinde'
;National Taiwan Normal University
Taiwan
;
_audit_update_record             
;
2023-08-25 deposited with the CCDC.	2024-03-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H23 N'
_chemical_formula_sum            'C27 H23 N'
_chemical_formula_weight         361.46

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'
N N 0.0311 0.0180 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   9.4988(2)
_cell_length_b                   11.9651(3)
_cell_length_c                   17.3667(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.1390(10)
_cell_angle_gamma                90.00
_cell_volume                     1958.49(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9842
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      66.74

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7505
_exptl_absorpt_correction_T_max  0.9338
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14764
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.98
_diffrn_reflns_theta_max         66.74
_reflns_number_total             3440
_reflns_number_gt                3028
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) 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     
'calc w=1/[σ²(Fo²)+(0.0653P)²+0.4016P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3440
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1342
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36108(16) 0.92446(13) 0.22113(9) 0.0526(4) Uani 1 1 d . . .
C2 C 0.32988(18) 0.83945(14) 0.16973(10) 0.0607(4) Uani 1 1 d . . .
H2 H 0.3091 0.7674 0.1884 0.073 Uiso 1 1 calc R . .
C3 C 0.32793(18) 0.85662(15) 0.08915(10) 0.0630(4) Uani 1 1 d . . .
H3 H 0.3075 0.7959 0.0543 0.076 Uiso 1 1 calc R . .
C4 C 0.35502(16) 0.95926(15) 0.06100(9) 0.0573(4) Uani 1 1 d . . .
H4 H 0.3516 0.9700 0.0066 0.069 Uiso 1 1 calc R . .
C5 C 0.38819(14) 1.04991(13) 0.11176(8) 0.0495(4) Uani 1 1 d . . .
C6 C 0.41926(16) 1.15722(14) 0.08411(9) 0.0565(4) Uani 1 1 d . . .
H6 H 0.4144 1.1693 0.0298 0.068 Uiso 1 1 calc R . .
C7 C 0.45590(18) 1.24326(15) 0.13353(10) 0.0601(4) Uani 1 1 d . . .
H7 H 0.4743 1.3151 0.1137 0.072 Uiso 1 1 calc R . .
C8 C 0.46654(17) 1.22570(14) 0.21426(10) 0.0585(4) Uani 1 1 d . . .
H8 H 0.4950 1.2854 0.2488 0.070 Uiso 1 1 calc R . .
C9 C 0.43628(16) 1.12372(13) 0.24320(9) 0.0530(4) Uani 1 1 d . . .
H9 H 0.4435 1.1137 0.2978 0.064 Uiso 1 1 calc R . .
C10 C 0.39453(15) 1.03289(13) 0.19389(8) 0.0491(4) Uani 1 1 d . . .
C11 C 0.26684(16) 0.96683(13) 0.34283(9) 0.0514(4) Uani 1 1 d . . .
C12 C 0.14037(17) 1.00808(13) 0.30385(9) 0.0527(4) Uani 1 1 d . . .
H12 H 0.1214 0.9992 0.2492 0.063 Uiso 1 1 calc R . .
C13 C 0.0419(2) 1.06173(14) 0.34338(11) 0.0637(4) Uani 1 1 d . . .
H13 H -0.0442 1.0884 0.3158 0.076 Uiso 1 1 calc R . .
C14 C 0.0683(2) 1.07660(15) 0.42278(11) 0.0728(5) Uani 1 1 d . . .
H14 H 0.0004 1.1126 0.4501 0.087 Uiso 1 1 calc R . .
C15 C 0.1942(3) 1.03853(16) 0.46166(11) 0.0751(5) Uani 1 1 d . . .
H15 H 0.2136 1.0497 0.5161 0.090 Uiso 1 1 calc R . .
C16 C 0.2936(2) 0.98403(16) 0.42275(10) 0.0653(4) Uani 1 1 d . . .
H16 H 0.3799 0.9584 0.4507 0.078 Uiso 1 1 calc R . .
C17 C 0.41793(17) 0.80005(14) 0.33504(10) 0.0579(4) Uani 1 1 d . . .
H17A H 0.3725 0.7397 0.3017 0.069 Uiso 1 1 calc R . .
H17B H 0.3887 0.7908 0.3874 0.069 Uiso 1 1 calc R . .
C18 C 0.57726(16) 0.78712(14) 0.34062(9) 0.0534(4) Uani 1 1 d . . .
C19 C 0.66280(19) 0.87266(16) 0.33053(11) 0.0666(5) Uani 1 1 d . . .
H19A H 0.7621 0.8609 0.3328 0.080 Uiso 1 1 calc R . .
H19B H 0.6245 0.9454 0.3211 0.080 Uiso 1 1 calc R . .
C20 C 0.63403(16) 0.67490(14) 0.35516(9) 0.0547(4) Uani 1 1 d . . .
H20 H 0.7315 0.6640 0.3502 0.066 Uiso 1 1 calc R . .
C21 C 0.56167(16) 0.58617(13) 0.37483(8) 0.0519(4) Uani 1 1 d . . .
H21 H 0.4661 0.5990 0.3834 0.062 Uiso 1 1 calc R . .
C22 C 0.61352(16) 0.47018(13) 0.38482(8) 0.0517(4) Uani 1 1 d . . .
C23 C 0.53540(18) 0.39300(15) 0.42208(10) 0.0591(4) Uani 1 1 d . . .
H23 H 0.4512 0.4169 0.4415 0.071 Uiso 1 1 calc R . .
C24 C 0.5768(2) 0.28269(16) 0.43152(11) 0.0695(5) Uani 1 1 d . . .
H24 H 0.5219 0.2319 0.4574 0.083 Uiso 1 1 calc R . .
C25 C 0.6991(2) 0.24640(17) 0.40296(11) 0.0721(5) Uani 1 1 d . . .
H25 H 0.7282 0.1706 0.4088 0.086 Uiso 1 1 calc R . .
C26 C 0.77805(19) 0.32175(16) 0.36592(11) 0.0672(5) Uani 1 1 d . . .
H26 H 0.8620 0.2974 0.3465 0.081 Uiso 1 1 calc R . .
C27 C 0.73645(17) 0.43211(15) 0.35676(10) 0.0600(4) Uani 1 1 d . . .
H27 H 0.7921 0.4826 0.3311 0.072 Uiso 1 1 calc R . .
N1 N 0.36584(14) 0.90864(11) 0.30330(8) 0.0560(3) 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
C1 C2 1.361(2) . ?
C1 C10 1.430(2) . ?
C1 N1 1.435(2) . ?
C2 C3 1.412(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.358(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.415(2) . ?
C5 C10 1.435(2) . ?
C6 C7 1.358(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.409(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.364(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.410(2) . ?
C9 H9 0.9500 . ?
C11 C12 1.394(2) . ?
C11 C16 1.395(2) . ?
C11 N1 1.415(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N1 1.473(2) . ?
C17 C18 1.512(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.332(2) . ?
C18 C20 1.457(2) . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?
C20 C21 1.332(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.476(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.393(2) . ?
C22 C27 1.396(2) . ?
C23 C24 1.381(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.382(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 120.01(15) . . ?
C2 C1 N1 122.07(15) . . ?
C10 C1 N1 117.90(14) . . ?
C1 C2 C3 121.06(16) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 120.56(16) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.57(15) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.76(14) . . ?
C4 C5 C10 119.44(14) . . ?
C6 C5 C10 118.79(14) . . ?
C7 C6 C5 121.44(15) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 119.81(15) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.52(16) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.47(15) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C1 123.76(14) . . ?
C9 C10 C5 117.93(14) . . ?
C1 C10 C5 118.29(14) . . ?
C12 C11 C16 118.06(15) . . ?
C12 C11 N1 121.57(14) . . ?
C16 C11 N1 120.37(15) . . ?
C13 C12 C11 121.19(15) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 120.29(17) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.05(17) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 121.22(17) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 120.15(17) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
N1 C17 C18 113.65(13) . . ?
N1 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
N1 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C20 120.81(15) . . ?
C19 C18 C17 122.35(15) . . ?
C20 C18 C17 116.81(14) . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C21 C20 C18 125.96(14) . . ?
C21 C20 H20 117.0 . . ?
C18 C20 H20 117.0 . . ?
C20 C21 C22 127.19(14) . . ?
C20 C21 H21 116.4 . . ?
C22 C21 H21 116.4 . . ?
C23 C22 C27 117.55(15) . . ?
C23 C22 C21 119.25(14) . . ?
C27 C22 C21 123.17(15) . . ?
C24 C23 C22 121.88(16) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C23 C24 C25 119.68(18) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 119.26(17) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C25 C26 C27 120.89(17) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C22 120.74(17) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?
C11 N1 C1 118.49(12) . . ?
C11 N1 C17 117.73(12) . . ?
C1 N1 C17 117.15(13) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        66.74
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_d24491
_database_code_depnum_ccdc_archive 'CCDC 2290697'
loop_
_audit_author_name
_audit_author_address
'Jivan Shinde'
;National Taiwan Normal University
Taiwan
;
_audit_update_record             
;
2023-08-25 deposited with the CCDC.	2024-03-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 O2'
_chemical_formula_sum            'C16 H14 O2'
_chemical_formula_weight         238.27

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'

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

_cell_length_a                   16.5657(15)
_cell_length_b                   5.4295(4)
_cell_length_c                   14.0697(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1265.48(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1999
_cell_measurement_theta_min      2.459
_cell_measurement_theta_max      24.279

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9437
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'phi scan & omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6361
_diffrn_reflns_av_R_equivalents  0.1282
_diffrn_reflns_av_sigmaI/netI    0.1105
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.26
_reflns_number_total             1825
_reflns_number_gt                1468
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) 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     
'calc w=1/[σ²(Fo²)+(0.0441P)²+0.0153P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.034(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4(2)
_refine_ls_number_reflns         1825
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2110(2) 0.3312(6) 0.6858(2) 0.0465(8) Uani 1 1 d . . .
H1 H 0.2520 0.2149 0.6711 0.056 Uiso 1 1 calc R . .
C2 C 0.1948(2) 0.5283(5) 0.6167(2) 0.0362(7) Uani 1 1 d . . .
C3 C 0.1303(2) 0.6892(5) 0.6315(2) 0.0433(8) Uani 1 1 d . . .
H3 H 0.0965 0.6671 0.6853 0.052 Uiso 1 1 calc R . .
C4 C 0.1149(2) 0.8798(6) 0.5693(2) 0.0479(9) Uani 1 1 d . . .
H4 H 0.0709 0.9887 0.5798 0.057 Uiso 1 1 calc R . .
C5 C 0.1648(2) 0.9090(5) 0.4914(3) 0.0469(9) Uani 1 1 d . . .
H5 H 0.1547 1.0407 0.4485 0.056 Uiso 1 1 calc R . .
C6 C 0.2287(2) 0.7534(5) 0.4738(2) 0.0401(8) Uani 1 1 d . . .
H6 H 0.2619 0.7767 0.4195 0.048 Uiso 1 1 calc R . .
C7 C 0.2441(2) 0.5614(5) 0.5369(2) 0.0344(7) Uani 1 1 d . . .
C8 C 0.3597(2) 0.4277(5) 0.4485(2) 0.0395(8) Uani 1 1 d . . .
H8A H 0.3811 0.5979 0.4474 0.047 Uiso 1 1 calc R . .
H8AB H 0.3300 0.3987 0.3885 0.047 Uiso 1 1 calc R . .
C9 C 0.42761(19) 0.2492(4) 0.45677(19) 0.0327(7) Uani 1 1 d . . .
C10 C 0.4304(2) 0.0879(5) 0.5273(2) 0.0493(9) Uani 1 1 d . . .
H10A H 0.4741 -0.0248 0.5315 0.059 Uiso 1 1 calc R . .
H10B H 0.3887 0.0848 0.5736 0.059 Uiso 1 1 calc R . .
C11 C 0.49053(18) 0.2657(4) 0.38143(19) 0.0324(7) Uani 1 1 d . . .
C12 C 0.5506(2) 0.0871(5) 0.3727(2) 0.0467(9) Uani 1 1 d . . .
H12 H 0.5510 -0.0486 0.4153 0.056 Uiso 1 1 calc R . .
C13 C 0.6098(2) 0.1031(6) 0.3033(2) 0.0559(11) Uani 1 1 d . . .
H13 H 0.6505 -0.0196 0.2994 0.067 Uiso 1 1 calc R . .
C14 C 0.6095(2) 0.2961(6) 0.2403(2) 0.0519(10) Uani 1 1 d . . .
H14 H 0.6492 0.3048 0.1918 0.062 Uiso 1 1 calc R . .
C15 C 0.5519(2) 0.4762(6) 0.2475(2) 0.0496(9) Uani 1 1 d . . .
H15 H 0.5524 0.6117 0.2048 0.060 Uiso 1 1 calc R . .
C16 C 0.4929(2) 0.4608(5) 0.3170(2) 0.0422(8) Uani 1 1 d . . .
H16 H 0.4530 0.5862 0.3208 0.051 Uiso 1 1 calc R . .
O1 O 0.17514(17) 0.3082(5) 0.76058(17) 0.0661(8) Uani 1 1 d . . .
O2 O 0.30616(13) 0.3987(3) 0.52734(14) 0.0431(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
C1 O1 1.215(4) . ?
C1 C2 1.471(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.396(4) . ?
C2 C7 1.399(4) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(4) . ?
C6 H6 0.9500 . ?
C7 O2 1.363(4) . ?
C8 O2 1.428(3) . ?
C8 C9 1.490(4) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.324(4) . ?
C9 C11 1.489(4) . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C11 C16 1.395(4) . ?
C11 C12 1.395(4) . ?
C12 C13 1.385(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.370(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
O1 C1 C2 123.9(3) . . ?
O1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C3 C2 C7 119.1(3) . . ?
C3 C2 C1 119.7(3) . . ?
C7 C2 C1 121.2(3) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 122.1(3) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 119.0(3) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
O2 C7 C6 124.1(3) . . ?
O2 C7 C2 115.9(2) . . ?
C6 C7 C2 120.1(3) . . ?
O2 C8 C9 109.7(2) . . ?
O2 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
O2 C8 H8AB 109.7 . . ?
C9 C8 H8AB 109.7 . . ?
H8A C8 H8AB 108.2 . . ?
C10 C9 C11 123.3(3) . . ?
C10 C9 C8 121.0(3) . . ?
C11 C9 C8 115.7(2) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C16 C11 C12 116.8(3) . . ?
C16 C11 C9 121.9(3) . . ?
C12 C11 C9 121.3(2) . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 121.6(3) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C7 O2 C8 118.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.26
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.040
