# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_ghh
_database_code_depnum_ccdc_archive 'CCDC 1542885'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N O'
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7206(15)
_cell_length_b                   13.742(3)
_cell_length_c                   14.038(3)
_cell_angle_alpha                94.322(9)
_cell_angle_beta                 90.117(9)
_cell_angle_gamma                90.020(9)
_cell_volume                     1485.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4383
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      32.16

_exptl_crystal_description       rectrangular
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.034
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.018
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.998
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11797
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         26.09
_reflns_number_total             5683
_reflns_number_gt                4072
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²+0.5000P] 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     SHELXL
_refine_ls_extinction_coef       0.062(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5683
_refine_ls_number_parameters     384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.2086
_refine_ls_wR_factor_gt          0.1859
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
O1 O 0.2186(2) 0.66071(14) 0.34113(16) 0.0807(6) Uani 1 1 d . . .
O2 O -0.2809(2) 0.33936(14) 0.15874(16) 0.0807(6) Uani 1 1 d . . .
N1 N 0.6857(2) 0.88351(12) 0.39613(12) 0.0408(4) Uani 1 1 d . . .
N2 N 0.1858(2) 0.11623(12) 0.10384(12) 0.0416(4) Uani 1 1 d . . .
C1 C 0.3690(3) 0.67726(18) 0.36352(18) 0.0579(6) Uani 1 1 d . . .
C2 C 0.4412(3) 0.77755(16) 0.36924(15) 0.0464(5) Uani 1 1 d . . .
C3 C 0.3361(3) 0.85680(17) 0.35413(15) 0.0487(5) Uani 1 1 d . . .
H3 H 0.2194 0.8473 0.3396 0.058 Uiso 1 1 calc R . .
C4 C 0.4049(3) 0.94951(16) 0.36076(14) 0.0435(5) Uani 1 1 d . . .
C5 C 0.5820(2) 0.95989(14) 0.38118(13) 0.0384(5) Uani 1 1 d . . .
C6 C 0.6628(2) 1.05723(14) 0.38896(13) 0.0390(5) Uani 1 1 d . . .
C7 C 0.8299(3) 1.07099(16) 0.42381(16) 0.0466(5) Uani 1 1 d . . .
H7 H 0.8933 1.0174 0.4407 0.056 Uiso 1 1 calc R . .
C8 C 0.9040(3) 1.16255(16) 0.43390(18) 0.0555(6) Uani 1 1 d . . .
H8 H 1.0157 1.1708 0.4582 0.067 Uiso 1 1 calc R . .
C9 C 0.8104(3) 1.24204(17) 0.40740(19) 0.0596(6) Uani 1 1 d . . .
H9 H 0.8583 1.3043 0.4146 0.071 Uiso 1 1 calc R . .
C10 C 0.6161(3) 0.79421(15) 0.39098(15) 0.0432(5) Uani 1 1 d . . .
C11 C 0.2952(3) 1.03943(18) 0.35373(18) 0.0549(6) Uani 1 1 d . . .
H11A H 0.1961 1.0232 0.3130 0.066 Uiso 1 1 calc R . .
H11B H 0.2523 1.0609 0.4167 0.066 Uiso 1 1 calc R . .
C12 C 0.3943(3) 1.12129(19) 0.31406(19) 0.0614(6) Uani 1 1 d . . .
H12A H 0.3269 1.1808 0.3230 0.074 Uiso 1 1 calc R . .
H12B H 0.4103 1.1067 0.2460 0.074 Uiso 1 1 calc R . .
C13 C 0.5695(3) 1.13772(16) 0.36094(15) 0.0467(5) Uani 1 1 d . . .
C14 C 0.6463(3) 1.22884(17) 0.37043(18) 0.0578(6) Uani 1 1 d . . .
H14 H 0.5855 1.2825 0.3513 0.069 Uiso 1 1 calc R . .
C15 C 0.7355(3) 0.71217(16) 0.4112(2) 0.0565(6) Uani 1 1 d . . .
H15A H 0.7418 0.7076 0.4797 0.068 Uiso 1 1 calc R . .
H15B H 0.8508 0.7272 0.3891 0.068 Uiso 1 1 calc R . .
C16 C 0.6797(3) 0.61321(17) 0.3638(2) 0.0643(7) Uani 1 1 d . . .
C17 C 0.6982(4) 0.6126(2) 0.2553(2) 0.0854(10) Uani 1 1 d . . .
H17A H 0.8178 0.6208 0.2393 0.128 Uiso 1 1 calc R . .
H17B H 0.6315 0.6650 0.2325 0.128 Uiso 1 1 calc R . .
H17C H 0.6568 0.5515 0.2261 0.128 Uiso 1 1 calc R . .
C18 C 0.4897(3) 0.59764(18) 0.3901(2) 0.0698(8) Uani 1 1 d . . .
H18A H 0.4506 0.5362 0.3587 0.084 Uiso 1 1 calc R . .
H18B H 0.4823 0.5922 0.4585 0.084 Uiso 1 1 calc R . .
C19 C 0.7923(4) 0.5330(2) 0.4010(3) 0.0991(12) Uani 1 1 d . . .
H19A H 0.7797 0.5331 0.4690 0.149 Uiso 1 1 calc R . .
H19B H 0.9114 0.5445 0.3857 0.149 Uiso 1 1 calc R . .
H19C H 0.7567 0.4708 0.3716 0.149 Uiso 1 1 calc R . .
C20 C 0.2923(4) 0.4669(2) 0.0983(3) 0.0979(12) Uani 1 1 d . . .
H20A H 0.2766 0.4676 0.0305 0.147 Uiso 1 1 calc R . .
H20B H 0.4117 0.4543 0.1119 0.147 Uiso 1 1 calc R . .
H20C H 0.2595 0.5290 0.1287 0.147 Uiso 1 1 calc R . .
C21 C 0.1793(3) 0.38688(17) 0.1359(2) 0.0642(7) Uani 1 1 d . . .
C22 C 0.2360(3) 0.28793(16) 0.0890(2) 0.0567(6) Uani 1 1 d . . .
H22A H 0.2431 0.2923 0.0205 0.068 Uiso 1 1 calc R . .
H22B H 0.3510 0.2731 0.1118 0.068 Uiso 1 1 calc R . .
C23 C 0.1158(3) 0.20564(15) 0.10892(15) 0.0443(5) Uani 1 1 d . . .
C24 C 0.0819(2) 0.04019(14) 0.11856(13) 0.0382(5) Uani 1 1 d . . .
C25 C 0.1631(2) -0.05758(14) 0.11117(14) 0.0402(5) Uani 1 1 d . . .
C26 C 0.0688(3) -0.13736(16) 0.13918(16) 0.0474(5) Uani 1 1 d . . .
C27 C 0.1459(3) -0.22904(17) 0.12907(19) 0.0586(6) Uani 1 1 d . . .
H27 H 0.0851 -0.2829 0.1476 0.070 Uiso 1 1 calc R . .
C28 C 0.3102(3) -0.24190(17) 0.09223(19) 0.0598(6) Uani 1 1 d . . .
H28 H 0.3580 -0.3041 0.0846 0.072 Uiso 1 1 calc R . .
C29 C -0.1312(3) 0.32311(18) 0.13635(18) 0.0576(6) Uani 1 1 d . . .
C30 C -0.0103(3) 0.40241(18) 0.1103(2) 0.0697(8) Uani 1 1 d . . .
H30A H -0.0487 0.4637 0.1422 0.084 Uiso 1 1 calc R . .
H30B H -0.0186 0.4084 0.0420 0.084 Uiso 1 1 calc R . .
C31 C -0.0951(3) 0.05023(16) 0.13921(14) 0.0437(5) Uani 1 1 d . . .
C32 C -0.1637(3) 0.14329(17) 0.14566(16) 0.0489(5) Uani 1 1 d . . .
H32 H -0.2803 0.1528 0.1599 0.059 Uiso 1 1 calc R . .
C33 C -0.0587(3) 0.22224(16) 0.13089(15) 0.0469(5) Uani 1 1 d . . .
C34 C -0.2047(3) -0.03946(17) 0.14598(17) 0.0535(6) Uani 1 1 d . . .
H34A H -0.2477 -0.0610 0.0829 0.064 Uiso 1 1 calc R . .
H34B H -0.3038 -0.0233 0.1865 0.064 Uiso 1 1 calc R . .
C35 C -0.1054(3) -0.12140(18) 0.18596(19) 0.0604(7) Uani 1 1 d . . .
H35A H -0.1727 -0.1810 0.1770 0.072 Uiso 1 1 calc R . .
H35B H -0.0891 -0.1068 0.2541 0.072 Uiso 1 1 calc R . .
C36 C 0.4037(3) -0.16281(17) 0.06675(19) 0.0572(6) Uani 1 1 d . . .
H36 H 0.5157 -0.1711 0.0432 0.069 Uiso 1 1 calc R . .
C37 C 0.3303(3) -0.07098(15) 0.07633(16) 0.0472(5) Uani 1 1 d . . .
H37 H 0.3936 -0.0174 0.0592 0.057 Uiso 1 1 calc R . .
C38 C 0.1991(4) 0.3874(2) 0.2447(2) 0.0871(10) Uani 1 1 d . . .
H38A H 0.1645 0.4497 0.2739 0.131 Uiso 1 1 calc R . .
H38B H 0.3179 0.3753 0.2604 0.131 Uiso 1 1 calc R . .
H38C H 0.1274 0.3373 0.2680 0.131 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.219(3) . ?
O2 C29 1.215(3) . ?
N1 C10 1.336(2) . ?
N1 C5 1.349(3) . ?
N2 C23 1.339(3) . ?
N2 C24 1.345(2) . ?
C1 C2 1.483(3) . ?
C1 C18 1.505(4) . ?
C2 C3 1.387(3) . ?
C2 C10 1.399(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(3) . ?
C4 C11 1.507(3) . ?
C5 C6 1.472(3) . ?
C6 C7 1.387(3) . ?
C6 C13 1.401(3) . ?
C7 C8 1.379(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(3) . ?
C8 H8 0.9300 . ?
C9 C14 1.375(4) . ?
C9 H9 0.9300 . ?
C10 C15 1.500(3) . ?
C11 C12 1.502(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.512(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.529(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C19 1.527(4) . ?
C16 C17 1.530(4) . ?
C16 C18 1.532(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.529(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C30 1.525(4) . ?
C21 C22 1.530(3) . ?
C21 C38 1.535(4) . ?
C22 C23 1.505(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C33 1.398(3) . ?
C24 C31 1.402(3) . ?
C24 C25 1.479(3) . ?
C25 C37 1.389(3) . ?
C25 C26 1.397(3) . ?
C26 C27 1.391(3) . ?
C26 C35 1.507(3) . ?
C27 C28 1.378(3) . ?
C27 H27 0.9300 . ?
C28 C36 1.374(3) . ?
C28 H28 0.9300 . ?
C29 C33 1.492(3) . ?
C29 C30 1.501(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.381(3) . ?
C31 C34 1.504(3) . ?
C32 C33 1.382(3) . ?
C32 H32 0.9300 . ?
C34 C35 1.505(4) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.381(3) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

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
C10 N1 C5 118.36(17) . . ?
C23 N2 C24 118.12(17) . . ?
O1 C1 C2 121.7(2) . . ?
O1 C1 C18 121.9(2) . . ?
C2 C1 C18 116.4(2) . . ?
C3 C2 C10 118.71(19) . . ?
C3 C2 C1 120.62(19) . . ?
C10 C2 C1 120.7(2) . . ?
C4 C3 C2 119.82(19) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.0(2) . . ?
C3 C4 C11 122.53(19) . . ?
C5 C4 C11 119.34(18) . . ?
N1 C5 C4 122.85(18) . . ?
N1 C5 C6 116.73(17) . . ?
C4 C5 C6 120.41(19) . . ?
C7 C6 C13 119.17(18) . . ?
C7 C6 C5 121.26(19) . . ?
C13 C6 C5 119.56(18) . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 119.2(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C14 C9 C8 119.9(2) . . ?
C14 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N1 C10 C2 122.3(2) . . ?
N1 C10 C15 116.32(17) . . ?
C2 C10 C15 121.41(18) . . ?
C12 C11 C4 112.22(19) . . ?
C12 C11 H11A 109.2 . . ?
C4 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C4 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 112.7(2) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C6 118.8(2) . . ?
C14 C13 C12 122.0(2) . . ?
C6 C13 C12 119.10(19) . . ?
C9 C14 C13 121.6(2) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C10 C15 C16 113.7(2) . . ?
C10 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C10 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C19 C16 C15 109.5(2) . . ?
C19 C16 C17 109.6(3) . . ?
C15 C16 C17 110.1(2) . . ?
C19 C16 C18 110.2(2) . . ?
C15 C16 C18 107.4(2) . . ?
C17 C16 C18 109.9(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 C18 C16 114.5(2) . . ?
C1 C18 H18A 108.6 . . ?
C16 C18 H18A 108.6 . . ?
C1 C18 H18B 108.6 . . ?
C16 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C30 C21 C20 110.4(2) . . ?
C30 C21 C22 108.1(2) . . ?
C20 C21 C22 109.0(2) . . ?
C30 C21 C38 109.8(2) . . ?
C20 C21 C38 109.8(3) . . ?
C22 C21 C38 109.7(2) . . ?
C23 C22 C21 113.48(19) . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
N2 C23 C33 122.33(19) . . ?
N2 C23 C22 116.11(18) . . ?
C33 C23 C22 121.55(19) . . ?
N2 C24 C31 123.18(18) . . ?
N2 C24 C25 116.64(17) . . ?
C31 C24 C25 120.18(17) . . ?
C37 C25 C26 119.87(19) . . ?
C37 C25 C24 120.99(18) . . ?
C26 C25 C24 119.14(18) . . ?
C27 C26 C25 118.2(2) . . ?
C27 C26 C35 121.9(2) . . ?
C25 C26 C35 119.8(2) . . ?
C28 C27 C26 121.5(2) . . ?
C28 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C36 C28 C27 120.0(2) . . ?
C36 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
O2 C29 C33 121.5(2) . . ?
O2 C29 C30 122.2(2) . . ?
C33 C29 C30 116.3(2) . . ?
C29 C30 C21 115.0(2) . . ?
C29 C30 H30A 108.5 . . ?
C21 C30 H30A 108.5 . . ?
C29 C30 H30B 108.5 . . ?
C21 C30 H30B 108.5 . . ?
H30A C30 H30B 107.5 . . ?
C32 C31 C24 117.66(19) . . ?
C32 C31 C34 122.62(19) . . ?
C24 C31 C34 119.56(19) . . ?
C31 C32 C33 119.89(19) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C32 C33 C23 118.8(2) . . ?
C32 C33 C29 120.6(2) . . ?
C23 C33 C29 120.6(2) . . ?
C31 C34 C35 112.15(18) . . ?
C31 C34 H34A 109.2 . . ?
C35 C34 H34A 109.2 . . ?
C31 C34 H34B 109.2 . . ?
C35 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
C34 C35 C26 112.38(19) . . ?
C34 C35 H35A 109.1 . . ?
C26 C35 H35A 109.1 . . ?
C34 C35 H35B 109.1 . . ?
C26 C35 H35B 109.1 . . ?
H35A C35 H35B 107.9 . . ?
C28 C36 C37 119.6(2) . . ?
C28 C36 H36 120.2 . . ?
C37 C36 H36 120.2 . . ?
C36 C37 C25 120.8(2) . . ?
C36 C37 H37 119.6 . . ?
C25 C37 H37 119.6 . . ?
C21 C38 H38A 109.5 . . ?
C21 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C21 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        26.10
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_appyr1_0m
_database_code_depnum_ccdc_archive 'CCDC 1542887'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H28 O4'
_chemical_formula_sum            'C25 H28 O4'
_chemical_formula_weight         392.47

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   9.9860(6)
_cell_length_b                   11.5723(7)
_cell_length_c                   18.8463(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.713(2)
_cell_angle_gamma                90.00
_cell_volume                     2152.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      30.77

_exptl_crystal_description       rectrangular
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9872
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36071
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         31.17
_reflns_number_total             6888
_reflns_number_gt                4850
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.0804P)²+0.2533P] 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         6888
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1525
_refine_ls_wR_factor_gt          0.1354
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.37185(10) 0.88082(9) 0.84320(5) 0.0570(3) Uani 1 1 d . . .
O2 O 0.55798(8) 0.74875(7) 1.07384(4) 0.0412(2) Uani 1 1 d . . .
O3 O 0.82478(10) 1.04121(8) 0.99152(5) 0.0532(2) Uani 1 1 d . . .
O4 O 0.71326(11) 0.66317(8) 0.94259(5) 0.0573(3) Uani 1 1 d . . .
C1 C 0.93500(17) 0.60543(17) 0.72604(9) 0.0724(5) Uani 1 1 d . . .
H1 H 0.9775 0.5773 0.6890 0.087 Uiso 1 1 calc R . .
C2 C 0.89173(16) 0.53028(15) 0.77397(8) 0.0642(4) Uani 1 1 d . . .
H2 H 0.9061 0.4514 0.7697 0.077 Uiso 1 1 calc R . .
C3 C 0.82680(14) 0.57133(12) 0.82870(7) 0.0509(3) Uani 1 1 d . . .
H3 H 0.7974 0.5198 0.8609 0.061 Uiso 1 1 calc R . .
C4 C 0.80521(11) 0.68938(11) 0.83577(6) 0.0405(3) Uani 1 1 d . . .
C5 C 0.73205(11) 0.72929(10) 0.89510(6) 0.0390(2) Uani 1 1 d . . .
C6 C 0.68029(12) 0.85176(10) 0.89162(6) 0.0401(2) Uani 1 1 d . . .
H6A H 0.6214 0.8621 0.8462 0.048 Uiso 1 1 calc R . .
H6B H 0.7569 0.9033 0.8917 0.048 Uiso 1 1 calc R . .
C7 C 0.60236(11) 0.88941(9) 0.95221(5) 0.0345(2) Uani 1 1 d . . .
H7 H 0.5721 0.9691 0.9421 0.041 Uiso 1 1 calc R . .
C8 C 0.47766(11) 0.81722(9) 0.95590(5) 0.0349(2) Uani 1 1 d . . .
C9 C 0.36687(12) 0.81788(10) 0.89486(6) 0.0418(3) Uani 1 1 d . . .
C10 C 0.24513(13) 0.74220(11) 0.89869(7) 0.0486(3) Uani 1 1 d . . .
H10A H 0.2100 0.7162 0.8505 0.058 Uiso 1 1 calc R . .
H10B H 0.1754 0.7889 0.9153 0.058 Uiso 1 1 calc R . .
C11 C 0.27062(12) 0.63613(10) 0.94733(6) 0.0423(3) Uani 1 1 d . . .
C12 C 0.35605(16) 0.54697(12) 0.91477(8) 0.0576(3) Uani 1 1 d . . .
H12A H 0.3107 0.5248 0.8682 0.086 Uiso 1 1 calc R . .
H12B H 0.3685 0.4802 0.9453 0.086 Uiso 1 1 calc R . .
H12C H 0.4427 0.5798 0.9104 0.086 Uiso 1 1 calc R . .
C13 C 0.13591(14) 0.58066(14) 0.95769(9) 0.0598(4) Uani 1 1 d . . .
H13A H 0.0908 0.5523 0.9124 0.090 Uiso 1 1 calc R . .
H13B H 0.0798 0.6372 0.9761 0.090 Uiso 1 1 calc R . .
H13C H 0.1526 0.5177 0.9910 0.090 Uiso 1 1 calc R . .
C14 C 0.46282(11) 0.75258(10) 1.01292(5) 0.0355(2) Uani 1 1 d . . .
C15 C 0.66856(11) 0.82053(10) 1.07814(6) 0.0357(2) Uani 1 1 d . . .
C16 C 0.69137(10) 0.88959(9) 1.02430(5) 0.0344(2) Uani 1 1 d . . .
C17 C 0.80679(11) 0.96898(10) 1.03666(6) 0.0399(2) Uani 1 1 d . . .
C18 C 0.90018(12) 0.96292(11) 1.10746(7) 0.0476(3) Uani 1 1 d . . .
H18A H 0.8731 1.0218 1.1391 0.057 Uiso 1 1 calc R . .
H18B H 0.9914 0.9812 1.0992 0.057 Uiso 1 1 calc R . .
C19 C 0.90293(12) 0.84632(11) 1.14567(7) 0.0450(3) Uani 1 1 d . . .
C20 C 0.97206(17) 0.75626(14) 1.10430(10) 0.0677(4) Uani 1 1 d . . .
H20A H 1.0637 0.7797 1.1024 0.102 Uiso 1 1 calc R . .
H20B H 0.9238 0.7496 1.0564 0.102 Uiso 1 1 calc R . .
H20C H 0.9722 0.6829 1.1281 0.102 Uiso 1 1 calc R . .
C21 C 0.75643(13) 0.81124(13) 1.14934(6) 0.0486(3) Uani 1 1 d . . .
H21A H 0.7549 0.7322 1.1664 0.058 Uiso 1 1 calc R . .
H21B H 0.7203 0.8604 1.1836 0.058 Uiso 1 1 calc R . .
C22 C 0.97986(16) 0.85867(17) 1.22177(8) 0.0704(4) Uani 1 1 d . . .
H22A H 0.9797 0.7860 1.2463 0.106 Uiso 1 1 calc R . .
H22B H 0.9367 0.9162 1.2472 0.106 Uiso 1 1 calc R . .
H22C H 1.0716 0.8815 1.2196 0.106 Uiso 1 1 calc R . .
C23 C 0.91578(18) 0.72229(18) 0.73261(9) 0.0731(5) Uani 1 1 d . . .
H23 H 0.9462 0.7731 0.7003 0.088 Uiso 1 1 calc R . .
C24 C 0.85082(15) 0.76462(14) 0.78756(7) 0.0559(3) Uani 1 1 d . . .
H24 H 0.8380 0.8438 0.7919 0.067 Uiso 1 1 calc R . .
C25 C 0.34450(12) 0.67716(11) 1.02006(6) 0.0434(3) Uani 1 1 d . . .
H25A H 0.2816 0.7195 1.0448 0.052 Uiso 1 1 calc R . .
H25B H 0.3755 0.6104 1.0491 0.052 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.2230(15) . ?
O2 C15 1.3743(13) . ?
O2 C14 1.3758(12) . ?
O3 C17 1.2252(14) . ?
O4 C5 1.2137(14) . ?
C1 C2 1.370(3) . ?
C1 C23 1.374(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.3828(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.3926(19) . ?
C3 H3 0.9300 . ?
C4 C24 1.3844(19) . ?
C4 C5 1.4983(15) . ?
C5 C6 1.5066(16) . ?
C6 C7 1.5390(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C16 1.5067(14) . ?
C7 C8 1.5098(15) . ?
C7 H7 0.9800 . ?
C8 C14 1.3360(15) . ?
C8 C9 1.4702(15) . ?
C9 C10 1.5088(18) . ?
C10 C11 1.5301(17) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.5257(18) . ?
C11 C13 1.5294(18) . ?
C11 C25 1.5303(16) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C25 1.4912(16) . ?
C15 C16 1.3380(15) . ?
C15 C21 1.4919(15) . ?
C16 C17 1.4647(16) . ?
C17 C18 1.5092(17) . ?
C18 C19 1.5278(18) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.528(2) . ?
C19 C22 1.5277(18) . ?
C19 C21 1.5298(17) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.3917(19) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 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
C15 O2 C14 118.48(8) . . ?
C2 C1 C23 120.20(14) . . ?
C2 C1 H1 119.9 . . ?
C23 C1 H1 119.9 . . ?
C1 C2 C3 120.27(15) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 120.35(14) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C24 C4 C3 118.89(11) . . ?
C24 C4 C5 122.82(11) . . ?
C3 C4 C5 118.29(11) . . ?
O4 C5 C4 120.23(11) . . ?
O4 C5 C6 122.33(10) . . ?
C4 C5 C6 117.41(10) . . ?
C5 C6 C7 116.28(9) . . ?
C5 C6 H6A 108.2 . . ?
C7 C6 H6A 108.2 . . ?
C5 C6 H6B 108.2 . . ?
C7 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
C16 C7 C8 109.71(8) . . ?
C16 C7 C6 111.96(9) . . ?
C8 C7 C6 113.01(9) . . ?
C16 C7 H7 107.3 . . ?
C8 C7 H7 107.3 . . ?
C6 C7 H7 107.3 . . ?
C14 C8 C9 118.05(10) . . ?
C14 C8 C7 122.66(9) . . ?
C9 C8 C7 119.29(9) . . ?
O1 C9 C8 120.63(11) . . ?
O1 C9 C10 120.93(10) . . ?
C8 C9 C10 118.41(10) . . ?
C9 C10 C11 115.61(9) . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 C13 108.89(11) . . ?
C12 C11 C10 110.73(11) . . ?
C13 C11 C10 110.09(10) . . ?
C12 C11 C25 110.30(10) . . ?
C13 C11 C25 109.27(11) . . ?
C10 C11 C25 107.55(10) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 O2 122.86(10) . . ?
C8 C14 C25 125.88(10) . . ?
O2 C14 C25 111.25(9) . . ?
C16 C15 O2 122.96(9) . . ?
C16 C15 C21 125.50(10) . . ?
O2 C15 C21 111.55(9) . . ?
C15 C16 C17 118.32(10) . . ?
C15 C16 C7 122.55(10) . . ?
C17 C16 C7 119.13(9) . . ?
O3 C17 C16 120.80(11) . . ?
O3 C17 C18 120.64(11) . . ?
C16 C17 C18 118.52(10) . . ?
C17 C18 C19 114.98(10) . . ?
C17 C18 H18A 108.5 . . ?
C19 C18 H18A 108.5 . . ?
C17 C18 H18B 108.5 . . ?
C19 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C20 C19 C22 109.94(12) . . ?
C20 C19 C18 109.83(12) . . ?
C22 C19 C18 109.30(12) . . ?
C20 C19 C21 110.56(12) . . ?
C22 C19 C21 109.31(11) . . ?
C18 C19 C21 107.86(10) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C21 C19 112.11(10) . . ?
C15 C21 H21A 109.2 . . ?
C19 C21 H21A 109.2 . . ?
C15 C21 H21B 109.2 . . ?
C19 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 C23 C24 120.04(16) . . ?
C1 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C4 C24 C23 120.25(15) . . ?
C4 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C14 C25 C11 112.45(10) . . ?
C14 C25 H25A 109.1 . . ?
C11 C25 H25A 109.1 . . ?
C14 C25 H25B 109.1 . . ?
C11 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        31.17
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.048
