# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mo_161206a_0m
_database_code_depnum_ccdc_archive 'CCDC 1562913'
_audit_update_record             
;
2017-07-18 deposited with the CCDC.
2017-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H27 N O3'
_chemical_formula_weight         557.62

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           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                   10.4521(18)
_cell_length_b                   10.3512(18)
_cell_length_c                   27.549(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.008(3)
_cell_angle_gamma                90.00
_cell_volume                     2943.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3884
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      22.10

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24738
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5119
_reflns_number_gt                3450
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0948P)²+1.2842P] 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         5119
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1912
_refine_ls_wR_factor_gt          0.1622
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.4270(2) -0.1011(2) 0.21369(9) 0.0425(6) Uani 1 1 d . . .
C2 C 0.4187(2) -0.1411(3) 0.16477(9) 0.0485(7) Uani 1 1 d . . .
H2 H 0.3874 -0.0840 0.1397 0.058 Uiso 1 1 calc R . .
C3 C 0.4556(2) -0.2624(3) 0.15314(9) 0.0454(6) Uani 1 1 d . . .
H3 H 0.4486 -0.2859 0.1203 0.054 Uiso 1 1 calc R . .
C4 C 0.5039(2) -0.3530(2) 0.18973(9) 0.0395(6) Uani 1 1 d . . .
C5 C 0.5146(2) -0.3105(3) 0.23797(9) 0.0439(6) Uani 1 1 d . . .
H5 H 0.5479 -0.3666 0.2632 0.053 Uiso 1 1 calc R . .
C6 C 0.4776(2) -0.1881(3) 0.24988(9) 0.0459(6) Uani 1 1 d . . .
H6 H 0.4867 -0.1636 0.2827 0.055 Uiso 1 1 calc R . .
C7 C 0.5423(2) -0.4861(2) 0.17812(9) 0.0403(6) Uani 1 1 d . . .
C8 C 0.5016(3) -0.5431(3) 0.13215(10) 0.0526(7) Uani 1 1 d . . .
H8 H 0.4487 -0.4966 0.1080 0.063 Uiso 1 1 calc R . .
C9 C 0.5385(3) -0.6660(3) 0.12222(10) 0.0547(7) Uani 1 1 d . . .
H9 H 0.5099 -0.7014 0.0914 0.066 Uiso 1 1 calc R . .
C10 C 0.6177(2) -0.7392(3) 0.15716(10) 0.0478(6) Uani 1 1 d . . .
C11 C 0.6592(2) -0.6839(3) 0.20235(10) 0.0480(7) Uani 1 1 d . . .
H11 H 0.7134 -0.7304 0.2261 0.058 Uiso 1 1 calc R . .
C12 C 0.6218(2) -0.5608(3) 0.21299(10) 0.0458(6) Uani 1 1 d . . .
H12 H 0.6500 -0.5265 0.2440 0.055 Uiso 1 1 calc R . .
C13 C 0.6548(3) -0.8723(3) 0.14649(11) 0.0579(7) Uani 1 1 d . . .
H13 H 0.6207 -0.9061 0.1159 0.069 Uiso 1 1 calc R . .
C14 C 0.4416(2) 0.0851(2) 0.27034(9) 0.0435(6) Uani 1 1 d . . .
C15 C 0.3655(2) 0.1405(3) 0.30115(10) 0.0479(7) Uani 1 1 d . . .
H15 H 0.2758 0.1382 0.2929 0.058 Uiso 1 1 calc R . .
C16 C 0.4212(2) 0.1992(3) 0.34411(10) 0.0469(6) Uani 1 1 d . . .
H16 H 0.3679 0.2351 0.3646 0.056 Uiso 1 1 calc R . .
C17 C 0.5545(2) 0.2065(3) 0.35781(9) 0.0431(6) Uani 1 1 d . . .
C18 C 0.6298(3) 0.1492(3) 0.32631(10) 0.0520(7) Uani 1 1 d . . .
H18 H 0.7196 0.1513 0.3344 0.062 Uiso 1 1 calc R . .
C19 C 0.5745(2) 0.0896(3) 0.28353(10) 0.0514(7) Uani 1 1 d . . .
H19 H 0.6273 0.0518 0.2633 0.062 Uiso 1 1 calc R . .
C20 C 0.6155(2) 0.2681(3) 0.40431(9) 0.0461(6) Uani 1 1 d . . .
C21 C 0.5503(3) 0.2811(4) 0.44418(11) 0.0698(9) Uani 1 1 d . . .
H21 H 0.4643 0.2549 0.4412 0.084 Uiso 1 1 calc R . .
C22 C 0.6097(4) 0.3317(4) 0.48799(12) 0.0810(11) Uani 1 1 d . . .
H22 H 0.5632 0.3387 0.5140 0.097 Uiso 1 1 calc R . .
C23 C 0.7368(3) 0.3724(3) 0.49428(10) 0.0635(8) Uani 1 1 d . . .
C24 C 0.8027(3) 0.3641(3) 0.45489(11) 0.0652(8) Uani 1 1 d . . .
H24 H 0.8880 0.3926 0.4581 0.078 Uiso 1 1 calc R . .
C25 C 0.7430(3) 0.3136(3) 0.41048(11) 0.0584(8) Uani 1 1 d . . .
H25 H 0.7889 0.3099 0.3842 0.070 Uiso 1 1 calc R . .
C26 C 0.7956(4) 0.4263(4) 0.54172(13) 0.0868(12) Uani 1 1 d . . .
H26 H 0.7438 0.4302 0.5662 0.104 Uiso 1 1 calc R . .
C27 C 0.2795(2) 0.0836(3) 0.19580(10) 0.0468(6) Uani 1 1 d . . .
C28 C 0.1662(3) 0.0147(3) 0.18117(11) 0.0553(7) Uani 1 1 d . . .
H28 H 0.1596 -0.0695 0.1923 0.066 Uiso 1 1 calc R . .
C29 C 0.0639(3) 0.0682(3) 0.15076(11) 0.0573(8) Uani 1 1 d . . .
H29 H -0.0109 0.0199 0.1415 0.069 Uiso 1 1 calc R . .
C30 C 0.0702(3) 0.1928(3) 0.13372(10) 0.0533(7) Uani 1 1 d . . .
C31 C 0.1838(3) 0.2635(3) 0.14977(10) 0.0565(7) Uani 1 1 d . . .
H31 H 0.1896 0.3485 0.1394 0.068 Uiso 1 1 calc R . .
C32 C 0.2871(3) 0.2093(3) 0.18065(10) 0.0521(7) Uani 1 1 d . . .
H32 H 0.3612 0.2578 0.1911 0.063 Uiso 1 1 calc R . .
C33 C -0.0409(3) 0.2498(3) 0.10024(10) 0.0581(8) Uani 1 1 d . . .
C34 C -0.1280(3) 0.1733(3) 0.06977(11) 0.0626(8) Uani 1 1 d . . .
H34 H -0.1185 0.0840 0.0712 0.075 Uiso 1 1 calc R . .
C35 C -0.2274(3) 0.2257(4) 0.03766(12) 0.0703(9) Uani 1 1 d . . .
H35 H -0.2838 0.1722 0.0173 0.084 Uiso 1 1 calc R . .
C36 C -0.2440(3) 0.3566(4) 0.03535(13) 0.0734(9) Uani 1 1 d . . .
C37 C -0.1639(4) 0.4321(4) 0.06660(15) 0.0922(13) Uani 1 1 d . . .
H37 H -0.1774 0.5209 0.0664 0.111 Uiso 1 1 calc R . .
C38 C -0.0634(4) 0.3803(4) 0.09862(14) 0.0843(11) Uani 1 1 d . . .
H38 H -0.0095 0.4346 0.1196 0.101 Uiso 1 1 calc R . .
C39 C -0.3500(4) 0.4157(5) 0.00115(16) 0.1043(15) Uani 1 1 d . . .
H39 H -0.3556 0.5054 0.0010 0.125 Uiso 1 1 calc R . .
N1 N 0.3863(2) 0.0231(2) 0.22589(8) 0.0500(6) Uani 1 1 d . . .
O1 O 0.7251(2) -0.9405(2) 0.17380(8) 0.0717(6) Uani 1 1 d . . .
O2 O -0.4286(4) 0.3587(4) -0.02616(13) 0.1378(13) Uani 1 1 d . . .
O3 O 0.9024(3) 0.4651(4) 0.55166(10) 0.1144(11) 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 C6 1.386(4) . ?
C1 C2 1.400(4) . ?
C1 N1 1.411(3) . ?
C2 C3 1.366(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.411(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 C7 1.483(4) . ?
C5 C6 1.380(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.400(4) . ?
C7 C8 1.401(4) . ?
C8 C9 1.369(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(4) . ?
C10 C13 1.472(4) . ?
C11 C12 1.378(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O1 1.196(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(4) . ?
C14 C19 1.381(3) . ?
C14 N1 1.423(3) . ?
C15 C16 1.376(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(4) . ?
C17 C20 1.483(4) . ?
C18 C19 1.375(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.387(4) . ?
C20 C25 1.399(4) . ?
C21 C22 1.372(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(4) . ?
C23 C26 1.465(5) . ?
C24 C25 1.386(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 O3 1.178(4) . ?
C26 H26 0.9300 . ?
C27 C32 1.373(4) . ?
C27 C28 1.387(4) . ?
C27 N1 1.426(3) . ?
C28 C29 1.368(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.377(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.405(4) . ?
C30 C33 1.488(4) . ?
C31 C32 1.385(4) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C38 1.370(5) . ?
C33 C34 1.386(4) . ?
C34 C35 1.367(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.366(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.351(5) . ?
C36 C39 1.471(5) . ?
C37 C38 1.371(5) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 O2 1.182(5) . ?
C39 H39 0.9300 . ?

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
C6 C1 C2 117.3(2) . . ?
C6 C1 N1 121.1(2) . . ?
C2 C1 N1 121.6(2) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 121.7(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 116.1(2) . . ?
C5 C4 C7 121.1(2) . . ?
C3 C4 C7 122.8(2) . . ?
C6 C5 C4 122.4(2) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C12 C7 C8 116.8(2) . . ?
C12 C7 C4 121.1(2) . . ?
C8 C7 C4 122.1(2) . . ?
C9 C8 C7 121.1(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 121.6(3) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C9 117.9(3) . . ?
C11 C10 C13 120.9(3) . . ?
C9 C10 C13 121.2(3) . . ?
C10 C11 C12 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C7 121.5(2) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
O1 C13 C10 125.5(3) . . ?
O1 C13 H13 117.2 . . ?
C10 C13 H13 117.2 . . ?
C15 C14 C19 118.6(2) . . ?
C15 C14 N1 121.5(2) . . ?
C19 C14 N1 119.9(2) . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 122.0(2) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C16 C17 C18 116.7(2) . . ?
C16 C17 C20 122.4(2) . . ?
C18 C17 C20 120.9(2) . . ?
C19 C18 C17 121.5(2) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C14 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C21 C20 C25 116.6(3) . . ?
C21 C20 C17 121.9(2) . . ?
C25 C20 C17 121.5(2) . . ?
C22 C21 C20 121.5(3) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 121.5(3) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 118.3(3) . . ?
C24 C23 C26 122.4(3) . . ?
C22 C23 C26 119.3(3) . . ?
C23 C24 C25 120.5(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C20 121.5(3) . . ?
C24 C25 H25 119.2 . . ?
C20 C25 H25 119.2 . . ?
O3 C26 C23 126.0(4) . . ?
O3 C26 H26 117.0 . . ?
C23 C26 H26 117.0 . . ?
C32 C27 C28 119.1(2) . . ?
C32 C27 N1 121.0(2) . . ?
C28 C27 N1 119.9(3) . . ?
C29 C28 C27 121.3(3) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C30 120.9(3) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C31 117.6(3) . . ?
C29 C30 C33 120.6(3) . . ?
C31 C30 C33 121.8(3) . . ?
C32 C31 C30 121.4(3) . . ?
C32 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
C27 C32 C31 119.6(3) . . ?
C27 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C38 C33 C34 116.8(3) . . ?
C38 C33 C30 121.6(3) . . ?
C34 C33 C30 121.5(3) . . ?
C35 C34 C33 121.7(3) . . ?
C35 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C36 C35 C34 120.1(3) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C37 C36 C35 118.8(3) . . ?
C37 C36 C39 119.8(4) . . ?
C35 C36 C39 121.3(3) . . ?
C36 C37 C38 121.3(4) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 H37 119.3 . . ?
C33 C38 C37 121.1(3) . . ?
C33 C38 H38 119.5 . . ?
C37 C38 H38 119.5 . . ?
O2 C39 C36 125.4(4) . . ?
O2 C39 H39 117.3 . . ?
C36 C39 H39 117.3 . . ?
C1 N1 C14 121.3(2) . . ?
C1 N1 C27 119.9(2) . . ?
C14 N1 C27 118.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1562912'
_audit_update_record             
;
2017-07-18 deposited with the CCDC.
2017-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H23 N O2'
_chemical_formula_weight         453.51

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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'
'-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                   11.9284(13)
_cell_length_b                   9.4890(11)
_cell_length_c                   20.901(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.007(2)
_cell_angle_gamma                90.00
_cell_volume                     2285.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5570
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      31.97

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9838
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            13927
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         28.99
_reflns_number_total             3039
_reflns_number_gt                2426
_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)+(0.0796P)²+0.5859P] 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         3039
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.82048(11) 0.01899(13) 0.55971(6) 0.0417(3) Uani 1 1 d . . .
C2 C 0.86457(11) 0.15472(14) 0.57097(5) 0.0428(3) Uani 1 1 d . . .
H2 H 0.8699 0.1978 0.6116 0.051 Uiso 1 1 calc R . .
C3 C 0.90050(11) 0.22619(13) 0.52228(5) 0.0410(3) Uani 1 1 d . . .
H3 H 0.9307 0.3167 0.5307 0.049 Uiso 1 1 calc R . .
C4 C 0.89214(9) 0.16428(11) 0.46056(5) 0.0348(2) Uani 1 1 d . . .
C5 C 0.85053(11) 0.02622(13) 0.45051(6) 0.0411(3) Uani 1 1 d . . .
H5 H 0.8467 -0.0179 0.4103 0.049 Uiso 1 1 calc R . .
C6 C 0.81517(11) -0.04566(13) 0.49901(6) 0.0432(3) Uani 1 1 d . . .
H6 H 0.7877 -0.1375 0.4914 0.052 Uiso 1 1 calc R . .
C7 C 0.92283(10) 0.24383(11) 0.40647(5) 0.0350(2) Uani 1 1 d . . .
C8 C 1.00435(11) 0.35261(13) 0.41921(5) 0.0419(3) Uani 1 1 d . . .
H8 H 1.0421 0.3746 0.4628 0.050 Uiso 1 1 calc R . .
C9 C 1.03023(11) 0.42841(13) 0.36836(6) 0.0443(3) Uani 1 1 d . . .
H9 H 1.0851 0.5002 0.3780 0.053 Uiso 1 1 calc R . .
C10 C 0.97441(10) 0.39761(12) 0.30280(5) 0.0383(3) Uani 1 1 d . . .
C11 C 0.89348(11) 0.28988(13) 0.28922(5) 0.0414(3) Uani 1 1 d . . .
H11 H 0.8561 0.2681 0.2455 0.050 Uiso 1 1 calc R . .
C12 C 0.86799(11) 0.21445(12) 0.34027(5) 0.0400(3) Uani 1 1 d . . .
H12 H 0.8132 0.1426 0.3303 0.048 Uiso 1 1 calc R . .
C13 C 0.77789(13) -0.05380(16) 0.61119(7) 0.0553(3) Uani 1 1 d . . .
H13 H 0.7818 -0.0046 0.6502 0.066 Uiso 1 1 calc R . .
C14 C 1.0000 0.62311(16) 0.2500 0.0369(3) Uani 1 2 d S . .
C15 C 0.92477(11) 0.69746(14) 0.27848(6) 0.0449(3) Uani 1 1 d . . .
H15 H 0.8740 0.6492 0.2978 0.054 Uiso 1 1 calc R . .
C16 C 0.92547(14) 0.84339(15) 0.27811(7) 0.0560(4) Uani 1 1 d . . .
H16 H 0.8748 0.8925 0.2971 0.067 Uiso 1 1 calc R . .
C17 C 1.0000 0.9166(2) 0.2500 0.0602(5) Uani 1 2 d S . .
H17 H 1.0000 1.0146 0.2500 0.072 Uiso 1 2 calc SR . .
N1 N 1.0000 0.47477(15) 0.2500 0.0457(4) Uani 1 2 d S . .
O1 O 0.73887(13) -0.17036(13) 0.60716(6) 0.0817(4) 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 1.3880(18) . ?
C1 C6 1.3959(17) . ?
C1 C13 1.4750(16) . ?
C2 C3 1.3803(16) . ?
C2 H2 0.9300 . ?
C3 C4 1.3974(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.3974(16) . ?
C4 C7 1.4821(14) . ?
C5 C6 1.3757(15) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.3956(16) . ?
C7 C12 1.3969(15) . ?
C8 C9 1.3827(16) . ?
C8 H8 0.9300 . ?
C9 C10 1.3907(16) . ?
C9 H9 0.9300 . ?
C10 C11 1.3840(17) . ?
C10 N1 1.4219(12) . ?
C11 C12 1.3826(15) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O1 1.1945(18) . ?
C13 H13 0.9300 . ?
C14 C15 1.3907(14) . ?
C14 C15 1.3907(14) 2_755 ?
C14 N1 1.408(2) . ?
C15 C16 1.3848(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.3742(19) . ?
C16 H16 0.9300 . ?
C17 C16 1.3742(19) 2_755 ?
C17 H17 0.9300 . ?
N1 C10 1.4219(12) 2_755 ?

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 C6 119.20(10) . . ?
C2 C1 C13 119.85(11) . . ?
C6 C1 C13 120.93(12) . . ?
C3 C2 C1 120.49(10) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.83(11) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.07(10) . . ?
C5 C4 C7 120.73(9) . . ?
C3 C4 C7 121.16(10) . . ?
C6 C5 C4 121.25(10) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 120.10(11) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 C7 C12 117.46(10) . . ?
C8 C7 C4 121.92(10) . . ?
C12 C7 C4 120.60(10) . . ?
C9 C8 C7 121.42(10) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 120.18(11) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.21(10) . . ?
C11 C10 N1 119.97(10) . . ?
C9 C10 N1 120.82(10) . . ?
C12 C11 C10 120.34(10) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 121.39(11) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
O1 C13 C1 125.71(13) . . ?
O1 C13 H13 117.1 . . ?
C1 C13 H13 117.1 . . ?
C15 C14 C15 119.03(16) . 2_755 ?
C15 C14 N1 120.49(8) . . ?
C15 C14 N1 120.49(8) 2_755 . ?
C16 C15 C14 119.96(13) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.88(13) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C16 119.30(18) . 2_755 ?
C16 C17 H17 120.4 . . ?
C16 C17 H17 120.4 2_755 . ?
C14 N1 C10 120.99(6) . 2_755 ?
C14 N1 C10 120.99(6) . . ?
C10 N1 C10 118.02(13) 2_755 . ?

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
C6 C1 C2 C3 1.35(19) . . . . ?
C13 C1 C2 C3 -177.45(12) . . . . ?
C1 C2 C3 C4 0.70(19) . . . . ?
C2 C3 C4 C5 -2.37(18) . . . . ?
C2 C3 C4 C7 175.70(10) . . . . ?
C3 C4 C5 C6 2.05(18) . . . . ?
C7 C4 C5 C6 -176.03(11) . . . . ?
C4 C5 C6 C1 -0.05(19) . . . . ?
C2 C1 C6 C5 -1.68(19) . . . . ?
C13 C1 C6 C5 177.11(12) . . . . ?
C5 C4 C7 C8 -153.80(12) . . . . ?
C3 C4 C7 C8 28.18(17) . . . . ?
C5 C4 C7 C12 27.99(16) . . . . ?
C3 C4 C7 C12 -150.03(12) . . . . ?
C12 C7 C8 C9 -0.13(18) . . . . ?
C4 C7 C8 C9 -178.40(11) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 C11 -0.41(18) . . . . ?
C8 C9 C10 N1 179.92(11) . . . . ?
C9 C10 C11 C12 0.40(18) . . . . ?
N1 C10 C11 C12 -179.92(10) . . . . ?
C10 C11 C12 C7 -0.26(18) . . . . ?
C8 C7 C12 C11 0.12(17) . . . . ?
C4 C7 C12 C11 178.41(11) . . . . ?
C2 C1 C13 O1 -179.59(15) . . . . ?
C6 C1 C13 O1 1.6(2) . . . . ?
C15 C14 C15 C16 0.07(9) 2_755 . . . ?
N1 C14 C15 C16 -179.93(9) . . . . ?
C14 C15 C16 C17 -0.15(19) . . . . ?
C15 C16 C17 C16 0.08(9) . . . 2_755 ?
C15 C14 N1 C10 147.67(8) . . . 2_755 ?
C15 C14 N1 C10 -32.33(8) 2_755 . . 2_755 ?
C15 C14 N1 C10 -32.33(8) . . . . ?
C15 C14 N1 C10 147.68(8) 2_755 . . . ?
C11 C10 N1 C14 130.41(9) . . . . ?
C9 C10 N1 C14 -49.92(12) . . . . ?
C11 C10 N1 C10 -49.59(9) . . . 2_755 ?
C9 C10 N1 C10 130.08(12) . . . 2_755 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_t_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1562914'
_audit_update_record             
;
2017-07-18 deposited with the CCDC.
2017-09-09 downloaded from the CCDC.
;
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_Int_Tables_number      29
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2+x,-y,z
4 1/2-x,y,1/2+z
_cell_length_a                   15.937(5)
_cell_length_b                   18.010(6)
_cell_length_c                   13.493(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3872.83
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C1 C 0.3264(5) 0.3910(4) 0.4673(6)
C2 C 0.4052(5) 0.3952(5) 0.4273(6)
H2 H 0.4457 0.4251 0.4568
C3 C 0.4244(7) 0.3556(7) 0.3443(8)
H3 H 0.4784 0.3572 0.3185
C4 C 0.3643(9) 0.3134(6) 0.2986(8)
H4 H 0.3771 0.2867 0.2416
C5 C 0.2856(8) 0.3109(5) 0.3376(8)
H5 H 0.2443 0.2833 0.3058
C6 C 0.2663(5) 0.3483(4) 0.4227(7)
H6 H 0.2128 0.3447 0.4499
C7 C 0.2426(4) 0.4813(4) 0.5609(7)
C8 C 0.1889(4) 0.4868(4) 0.6407(7)
H8 H 0.1951 0.4551 0.6946
C9 C 0.1254(5) 0.5398(6) 0.6405(10)
H9 H 0.0903 0.5438 0.6953
C10 C 0.1136(7) 0.5860(7) 0.5619(11)
H10 H 0.0717 0.6219 0.5633
C11 C 0.1647(6) 0.5789(5) 0.4806(9)
H11 H 0.1557 0.6089 0.4255
C12 C 0.2301(5) 0.5272(4) 0.4796(8)
H12 H 0.2650 0.5235 0.4246
C13 C 0.3568(4) 0.4126(4) 0.6433(6)
C14 C 0.3683(4) 0.4640(4) 0.7184(6)
H14 H 0.3425 0.5102 0.7144
C15 C 0.4176(4) 0.4472(3) 0.7985(6)
H15 H 0.4245 0.4827 0.8479
C16 C 0.4576(4) 0.3793(4) 0.8086(6)
C17 C 0.4443(5) 0.3285(4) 0.7334(6)
H17 H 0.4697 0.2821 0.7376
C18 C 0.3950(5) 0.3441(4) 0.6527(6)
H18 H 0.3873 0.3082 0.6039
C19 C 0.5128(4) 0.3636(4) 0.8937(6)
C20 C 0.4980(5) 0.3936(4) 0.9874(6)
H20 H 0.4505 0.4227 0.9974
C21 C 0.5516(5) 0.3814(4) 1.0649(6)
H21 H 0.5391 0.4010 1.1270
C22 C 0.6242(5) 0.3400(4) 1.0521(7)
C23 C 0.6387(5) 0.3098(4) 0.9601(7)
H23 H 0.6862 0.2806 0.9502
C24 C 0.5850(5) 0.3217(4) 0.8830(7)
H24 H 0.5973 0.3010 0.8215
C25 C 0.6845(6) 0.3286(5) 1.1335(8)
H25 H 0.7321 0.3006 1.1194
N1 N 0.3076(4) 0.4281(3) 0.5587(5)
O1 O 0.6780(4) 0.3522(3) 1.2162(5)
C26 C 0.3310(4) 0.0898(4) -0.2165(5)
C27 C 0.4124(4) 0.0885(4) -0.2519(6)
H27 H 0.4538 0.0644 -0.2154
C28 C 0.4333(6) 0.1219(5) -0.3397(6)
H28 H 0.4886 0.1215 -0.3616
C29 C 0.3720(6) 0.1558(4) -0.3951(7)
H29 H 0.3853 0.1778 -0.4555
C30 C 0.2912(6) 0.1571(4) -0.3607(7)
H30 H 0.2498 0.1803 -0.3982
C31 C 0.2704(5) 0.1251(4) -0.2726(6)
H31 H 0.2153 0.1270 -0.2501
C32 C 0.2483(4) -0.0002(3) -0.1233(6)
C33 C 0.2393(5) -0.0487(4) -0.2020(6)
H33 H 0.2754 -0.0449 -0.2559
C34 C 0.1781(6) -0.1024(4) -0.2021(8)
H34 H 0.1735 -0.1353 -0.2550
C35 C 0.1232(5) -0.1071(5) -0.1230(8)
H35 H 0.0809 -0.1427 -0.1232
C36 C 0.1309(4) -0.0597(5) -0.0444(7)
H36 H 0.0945 -0.0640 0.0092
C37 C 0.1917(4) -0.0058(4) -0.0436(6)
H37 H 0.1955 0.0269 0.0095
C38 C 0.3569(4) 0.0737(4) -0.0378(5)
C39 C 0.3926(4) 0.1444(4) -0.0286(5)
H39 H 0.3851 0.1792 -0.0787
C40 C 0.4388(4) 0.1626(4) 0.0542(5)
H40 H 0.4636 0.2093 0.0580
C41 C 0.4494(4) 0.1130(4) 0.1324(5)
C42 C 0.4137(4) 0.0429(4) 0.1212(5)
H42 H 0.4203 0.0082 0.1716
C43 C 0.3686(4) 0.0232(4) 0.0375(5)
H43 H 0.3462 -0.0243 0.0321
C44 C 0.4973(4) 0.1315(3) 0.2216(5)
C45 C 0.5628(5) 0.1819(4) 0.2180(6)
H45 H 0.5777 0.2039 0.1582
C46 C 0.6064(5) 0.1997(4) 0.3048(6)
H46 H 0.6501 0.2338 0.3017
C47 C 0.5868(4) 0.1687(4) 0.3930(6)
C48 C 0.5238(4) 0.1178(4) 0.3981(6)
H48 H 0.5108 0.0953 0.4582
C49 C 0.4794(4) 0.0999(4) 0.3139(5)
H49 H 0.4360 0.0656 0.3186
C50 C 0.6356(6) 0.1905(5) 0.4822(7)
H50 H 0.6779 0.2252 0.4719
N2 N 0.3105(3) 0.0556(3) -0.1250(4)
O2 O 0.6276(4) 0.1695(4) 0.5637(5)
