# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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. 
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data_dr1
_database_code_depnum_ccdc_archive 'CCDC 1567243'
_audit_update_record             
;
2017-08-07 deposited with the CCDC.
2017-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        1
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H29 N3 O3'
_chemical_formula_sum            'C34 H29 N3 O3'
_chemical_formula_weight         527.60

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   14.0571(5)
_cell_length_b                   13.2680(5)
_cell_length_c                   15.3305(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.9640(10)
_cell_angle_gamma                90
_cell_volume                     2762.32(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4848
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      24.994

_exptl_crystal_description       Plate
_exptl_crystal_colour            yellowish
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.328
_exptl_crystal_size_min          0.265
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49739
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.331
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4848
_reflns_number_gt                3522
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1346P)²+2.7155P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4848
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0784
_refine_ls_wR_factor_ref         0.2532
_refine_ls_wR_factor_gt          0.2266
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_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 0.21687(18) 0.68416(15) 0.37602(14) 0.0454(6) Uani 1 1 d . . . . .
O1 O 0.2614(2) 0.77551(17) 0.27317(16) 0.0590(7) Uani 1 1 d . . . . .
N2 N 0.28263(18) 0.60847(19) 0.16926(16) 0.0382(6) Uani 1 1 d . . . . .
N1 N 0.2964(2) 0.6396(2) 0.03194(17) 0.0424(7) Uani 1 1 d . . . . .
O3 O 0.1463(2) 0.5911(3) -0.10273(18) 0.0811(10) Uani 1 1 d . . . . .
H3 H 0.2036 0.6053 -0.0774 0.122 Uiso 1 1 calc R U . . .
C10 C 0.2460(2) 0.5994(2) 0.2474(2) 0.0354(7) Uani 1 1 d . . . . .
C11 C 0.2436(2) 0.6920(2) 0.2963(2) 0.0394(7) Uani 1 1 d . . . . .
C13 C 0.1919(2) 0.5047(2) 0.3592(2) 0.0382(7) Uani 1 1 d . . . . .
C2 C 0.3834(2) 0.6061(2) 0.1739(2) 0.0396(7) Uani 1 1 d . . . . .
C1 C 0.2331(2) 0.6304(2) 0.0819(2) 0.0381(7) Uani 1 1 d . . . . .
C3 C 0.3901(2) 0.6252(2) 0.0877(2) 0.0406(7) Uani 1 1 d . . . . .
C12 C 0.2205(2) 0.5107(2) 0.2774(2) 0.0375(7) Uani 1 1 d . . . . .
H12 H 0.2218 0.4525 0.2439 0.045 Uiso 1 1 calc R U . . .
C18 C 0.1928(2) 0.5933(2) 0.4088(2) 0.0385(7) Uani 1 1 d . . . . .
C19 C 0.4555(2) 0.5818(3) 0.2599(2) 0.0453(8) Uani 1 1 d . . . . .
C4 C 0.1264(2) 0.6364(2) 0.0442(2) 0.0431(8) Uani 1 1 d . . . . .
C30 C 0.4757(3) 0.6274(2) 0.0493(2) 0.0463(8) Uani 1 1 d . . . . .
C14 C 0.1662(3) 0.4162(2) 0.3981(2) 0.0489(8) Uani 1 1 d . . . . .
H14 H 0.1648 0.3553 0.3678 0.059 Uiso 1 1 calc R U . . .
C17 C 0.1706(3) 0.5975(3) 0.4907(2) 0.0485(8) Uani 1 1 d . . . . .
H17 H 0.1729 0.6585 0.5210 0.058 Uiso 1 1 calc R U . . .
N3 N 0.1200(3) 0.5103(3) 0.6085(2) 0.0824(12) Uani 1 1 d . . . . .
C9 C 0.0602(3) 0.6640(3) 0.0940(3) 0.0599(10) Uani 1 1 d . . . . .
H9 H 0.0841 0.6815 0.1544 0.072 Uiso 1 1 calc R U . . .
C29 C 0.4621(3) 0.6544(3) -0.0410(3) 0.0586(10) Uani 1 1 d . . . . .
H29 H 0.3997 0.6730 -0.0749 0.070 Uiso 1 1 calc R U . . .
C20 C 0.4589(3) 0.4865(3) 0.2970(3) 0.0605(10) Uani 1 1 d . . . . .
H20 H 0.4165 0.4366 0.2667 0.073 Uiso 1 1 calc R U . . .
C5 C 0.0875(3) 0.6134(3) -0.0472(2) 0.0563(9) Uani 1 1 d . . . . .
C15 C 0.1432(3) 0.4172(3) 0.4793(3) 0.0590(10) Uani 1 1 d . . . . .
H15 H 0.1265 0.3571 0.5029 0.071 Uiso 1 1 calc R U . . .
C16 C 0.1441(3) 0.5081(3) 0.5287(2) 0.0551(9) Uani 1 1 d . . . . .
C24 C 0.5206(3) 0.6546(3) 0.3059(3) 0.0657(11) Uani 1 1 d . . . . .
H24 H 0.5192 0.7192 0.2821 0.079 Uiso 1 1 calc R U . . .
C25 C 0.5697(3) 0.6010(3) 0.0973(3) 0.0610(10) Uani 1 1 d . . . . .
H25 H 0.5813 0.5830 0.1578 0.073 Uiso 1 1 calc R U . . .
C26 C 0.6472(3) 0.6009(3) 0.0564(4) 0.0723(12) Uani 1 1 d . . . . .
H26 H 0.7101 0.5833 0.0899 0.087 Uiso 1 1 calc R U . . .
C27 C 0.6321(3) 0.6263(3) -0.0314(4) 0.0718(13) Uani 1 1 d . . . . .
H27 H 0.6842 0.6253 -0.0584 0.086 Uiso 1 1 calc R U . . .
C8 C -0.0401(3) 0.6659(4) 0.0555(3) 0.0719(12) Uani 1 1 d . . . . .
H8 H -0.0831 0.6841 0.0898 0.086 Uiso 1 1 calc R U . . .
C28 C 0.5395(4) 0.6538(3) -0.0809(3) 0.0718(12) Uani 1 1 d . . . . .
H28 H 0.5291 0.6720 -0.1412 0.086 Uiso 1 1 calc R U . . .
C6 C -0.0124(3) 0.6143(4) -0.0847(3) 0.0720(12) Uani 1 1 d . . . . .
H6 H -0.0371 0.5968 -0.1451 0.086 Uiso 1 1 calc R U . . .
C7 C -0.0761(3) 0.6403(4) -0.0349(3) 0.0757(13) Uani 1 1 d . . . . .
H7 H -0.1436 0.6409 -0.0613 0.091 Uiso 1 1 calc R U . . .
C22 C 0.5884(4) 0.5373(5) 0.4236(3) 0.0871(16) Uani 1 1 d . . . . .
H22 H 0.6323 0.5225 0.4787 0.105 Uiso 1 1 calc R U . . .
C23 C 0.5875(4) 0.6312(4) 0.3870(3) 0.0849(15) Uani 1 1 d . . . . .
H23 H 0.6320 0.6798 0.4166 0.102 Uiso 1 1 calc R U . . .
C21 C 0.5248(3) 0.4646(4) 0.3791(3) 0.0801(14) Uani 1 1 d . . . . .
H21 H 0.5258 0.4005 0.4039 0.096 Uiso 1 1 calc R U . . .
C31 C 0.1266(5) 0.6033(5) 0.6605(4) 0.1043(14) Uani 1 1 d . . . . .
H31A H 0.0874 0.5957 0.7037 0.125 Uiso 1 1 calc R U . . .
H31B H 0.0979 0.6575 0.6198 0.125 Uiso 1 1 calc R U . . .
C32 C 0.2304(7) 0.6335(7) 0.7112(5) 0.154(2) Uani 1 1 d . . . . .
H32A H 0.2587 0.5818 0.7538 0.232 Uiso 1 1 calc R U . . .
H32B H 0.2283 0.6957 0.7426 0.232 Uiso 1 1 calc R U . . .
H32C H 0.2699 0.6421 0.6691 0.232 Uiso 1 1 calc R U . . .
C33 C 0.0793(5) 0.4215(5) 0.6434(4) 0.1043(14) Uani 1 1 d . . . . .
H33A H 0.0286 0.4411 0.6725 0.125 Uiso 1 1 calc R U . . .
H33B H 0.0511 0.3748 0.5948 0.125 Uiso 1 1 calc R U . . .
C34 C 0.1544(7) 0.3800(7) 0.7020(5) 0.154(2) Uani 1 1 d . . . . .
H34A H 0.1912 0.3392 0.6705 0.232 Uiso 1 1 calc R U . . .
H34B H 0.1306 0.3387 0.7432 0.232 Uiso 1 1 calc R U . . .
H34C H 0.1962 0.4319 0.7349 0.232 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
O2 C11 1.372(4) . ?
O2 C18 1.381(4) . ?
O1 C11 1.209(4) . ?
N2 C1 1.372(4) . ?
N2 C2 1.400(4) . ?
N2 C10 1.427(4) . ?
N1 C1 1.320(4) . ?
N1 C3 1.386(4) . ?
O3 C5 1.364(5) . ?
O3 H3 0.8200 . ?
C10 C12 1.344(4) . ?
C10 C11 1.445(4) . ?
C13 C18 1.397(4) . ?
C13 C14 1.407(4) . ?
C13 C12 1.415(4) . ?
C2 C3 1.372(4) . ?
C2 C19 1.476(5) . ?
C1 C4 1.463(5) . ?
C3 C30 1.470(4) . ?
C12 H12 0.9300 . ?
C18 C17 1.372(4) . ?
C19 C20 1.383(5) . ?
C19 C24 1.390(5) . ?
C4 C9 1.397(5) . ?
C4 C5 1.400(5) . ?
C30 C25 1.382(5) . ?
C30 C29 1.395(5) . ?
C14 C15 1.365(5) . ?
C14 H14 0.9300 . ?
C17 C16 1.412(5) . ?
C17 H17 0.9300 . ?
N3 C16 1.353(5) . ?
N3 C31 1.459(6) . ?
N3 C33 1.469(6) . ?
C9 C8 1.380(5) . ?
C9 H9 0.9300 . ?
C29 C28 1.379(5) . ?
C29 H29 0.9300 . ?
C20 C21 1.386(6) . ?
C20 H20 0.9300 . ?
C5 C6 1.374(6) . ?
C15 C16 1.422(5) . ?
C15 H15 0.9300 . ?
C24 C23 1.387(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.391(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.351(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.376(7) . ?
C27 H27 0.9300 . ?
C8 C7 1.389(6) . ?
C8 H8 0.9300 . ?
C28 H28 0.9300 . ?
C6 C7 1.362(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C22 C23 1.366(7) . ?
C22 C21 1.372(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C21 H21 0.9300 . ?
C31 C32 1.519(10) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.317(9) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 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
C11 O2 C18 122.6(2) . . ?
C1 N2 C2 107.8(2) . . ?
C1 N2 C10 129.5(3) . . ?
C2 N2 C10 122.4(2) . . ?
C1 N1 C3 107.8(3) . . ?
C5 O3 H3 109.5 . . ?
C12 C10 N2 123.1(3) . . ?
C12 C10 C11 121.6(3) . . ?
N2 C10 C11 115.1(3) . . ?
O1 C11 O2 117.1(3) . . ?
O1 C11 C10 126.4(3) . . ?
O2 C11 C10 116.4(3) . . ?
C18 C13 C14 116.0(3) . . ?
C18 C13 C12 118.0(3) . . ?
C14 C13 C12 125.9(3) . . ?
C3 C2 N2 105.5(3) . . ?
C3 C2 C19 134.3(3) . . ?
N2 C2 C19 120.2(3) . . ?
N1 C1 N2 109.7(3) . . ?
N1 C1 C4 122.8(3) . . ?
N2 C1 C4 127.4(3) . . ?
C2 C3 N1 109.2(3) . . ?
C2 C3 C30 131.0(3) . . ?
N1 C3 C30 119.8(3) . . ?
C10 C12 C13 120.9(3) . . ?
C10 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C17 C18 O2 115.6(3) . . ?
C17 C18 C13 124.0(3) . . ?
O2 C18 C13 120.3(3) . . ?
C20 C19 C24 118.5(3) . . ?
C20 C19 C2 120.7(3) . . ?
C24 C19 C2 120.8(3) . . ?
C9 C4 C5 117.4(3) . . ?
C9 C4 C1 124.0(3) . . ?
C5 C4 C1 118.6(3) . . ?
C25 C30 C29 117.4(3) . . ?
C25 C30 C3 123.5(3) . . ?
C29 C30 C3 119.1(3) . . ?
C15 C14 C13 121.7(3) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C16 N3 C31 121.1(3) . . ?
C16 N3 C33 121.6(4) . . ?
C31 N3 C33 117.1(4) . . ?
C8 C9 C4 121.5(4) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
C28 C29 C30 121.2(4) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C19 C20 C21 120.6(4) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
O3 C5 C6 117.4(4) . . ?
O3 C5 C4 121.9(3) . . ?
C6 C5 C4 120.7(4) . . ?
C14 C15 C16 121.5(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
N3 C16 C17 120.6(3) . . ?
N3 C16 C15 122.0(3) . . ?
C17 C16 C15 117.4(3) . . ?
C23 C24 C19 120.3(4) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C30 C25 C26 120.9(4) . . ?
C30 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C27 C26 C25 120.6(4) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 119.9(4) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C9 C8 C7 119.4(4) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C27 C28 C29 120.0(4) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C7 C6 C5 121.1(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 119.9(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C23 C22 C21 120.1(4) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.3(5) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C22 C21 C20 120.1(5) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
N3 C31 C32 114.9(6) . . ?
N3 C31 H31A 108.6 . . ?
C32 C31 H31A 108.6 . . ?
N3 C31 H31B 108.6 . . ?
C32 C31 H31B 108.6 . . ?
H31A C31 H31B 107.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 N3 105.3(7) . . ?
C34 C33 H33A 110.7 . . ?
N3 C33 H33A 110.7 . . ?
C34 C33 H33B 110.7 . . ?
N3 C33 H33B 110.7 . . ?
H33A C33 H33B 108.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

_refine_diff_density_max         1.240
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.058



####################################################################### 
# 
# 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_dr3
_database_code_depnum_ccdc_archive 'CCDC 1567244'
_audit_update_record             
;
2017-08-07 deposited with the CCDC.
2017-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H29 N3 O2'
_chemical_formula_sum            'C34 H29 N3 O2'
_chemical_formula_weight         511.60

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.8322(6)
_cell_length_b                   11.6973(7)
_cell_length_c                   12.9750(7)
_cell_angle_alpha                113.245(2)
_cell_angle_beta                 93.220(2)
_cell_angle_gamma                93.119(2)
_cell_volume                     1364.18(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    5179
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      25.681

_exptl_crystal_description       Plate
_exptl_crystal_colour            yellowish
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             594
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.034
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41215
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_av_R_equivalents  0.0828
_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       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.583
_diffrn_reflns_theta_max         25.681
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5179
_reflns_number_gt                2910
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0523P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5179
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1332
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_restrained_S_all      1.218
_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_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 0.40958(14) 0.62491(13) 0.48852(11) 0.0604(4) Uani 1 1 d . . . . .
N2 N 0.52675(16) 0.55875(14) 0.20948(12) 0.0495(4) Uani 1 1 d . . . . .
N1 N 0.72514(17) 0.57456(15) 0.14014(13) 0.0517(4) Uani 1 1 d . . . . .
O1 O 0.61406(16) 0.59108(17) 0.42487(13) 0.0821(5) Uani 1 1 d . . . . .
N3 N -0.01990(17) 0.68517(15) 0.64378(13) 0.0567(5) Uani 1 1 d . . . . .
C13 C 0.2123(2) 0.61268(17) 0.36531(15) 0.0447(5) Uani 1 1 d . . . . .
C12 C 0.2989(2) 0.59010(17) 0.27670(15) 0.0489(5) Uani 1 1 d . . . . .
H12 H 0.2621 0.5794 0.2056 0.059 Uiso 1 1 calc R U . . .
C1 C 0.6388(2) 0.63626(18) 0.21146(16) 0.0503(5) Uani 1 1 d . . . . .
C10 C 0.4333(2) 0.58403(17) 0.29461(15) 0.0463(5) Uani 1 1 d . . . . .
C19 C 0.4603(2) 0.32658(18) 0.11715(15) 0.0464(5) Uani 1 1 d . . . . .
C3 C 0.6700(2) 0.45178(18) 0.09120(15) 0.0471(5) Uani 1 1 d . . . . .
C14 C 0.2707(2) 0.62911(17) 0.47096(15) 0.0454(5) Uani 1 1 d . . . . .
C16 C 0.0560(2) 0.66153(17) 0.55411(15) 0.0476(5) Uani 1 1 d . . . . .
C17 C -0.0057(2) 0.64376(18) 0.44687(16) 0.0529(5) Uani 1 1 d . . . . .
H17 H -0.0995 0.6484 0.4375 0.063 Uiso 1 1 calc R U . . .
C30 C 0.7429(2) 0.35825(18) 0.00503(16) 0.0493(5) Uani 1 1 d . . . . .
C2 C 0.5491(2) 0.43914(18) 0.13397(15) 0.0471(5) Uani 1 1 d . . . . .
C15 C 0.1974(2) 0.65286(18) 0.56282(15) 0.0519(5) Uani 1 1 d . . . . .
H15 H 0.2418 0.6633 0.6315 0.062 Uiso 1 1 calc R U . . .
C18 C 0.0709(2) 0.61996(18) 0.35728(16) 0.0525(5) Uani 1 1 d . . . . .
H18 H 0.0272 0.6081 0.2879 0.063 Uiso 1 1 calc R U . . .
C25 C 0.6772(2) 0.24741(19) -0.07393(17) 0.0597(6) Uani 1 1 d . . . . .
H25 H 0.5839 0.2299 -0.0735 0.072 Uiso 1 1 calc R U . . .
C4 C 0.6623(2) 0.77041(19) 0.28207(16) 0.0535(6) Uani 1 1 d . . . . .
C20 C 0.3350(2) 0.2986(2) 0.05696(17) 0.0633(6) Uani 1 1 d . . . . .
H20 H 0.2998 0.3555 0.0310 0.076 Uiso 1 1 calc R U . . .
C29 C 0.8819(2) 0.3804(2) 0.00051(17) 0.0564(6) Uani 1 1 d . . . . .
H29 H 0.9280 0.4537 0.0529 0.068 Uiso 1 1 calc R U . . .
C31 C -0.1655(2) 0.7016(2) 0.63573(18) 0.0609(6) Uani 1 1 d . . . . .
H31A H -0.2059 0.6920 0.6987 0.073 Uiso 1 1 calc R U . . .
H31B H -0.2083 0.6360 0.5672 0.073 Uiso 1 1 calc R U . . .
C11 C 0.4948(2) 0.59847(19) 0.40314(17) 0.0563(6) Uani 1 1 d . . . . .
C26 C 0.7508(2) 0.1632(2) -0.15308(18) 0.0661(6) Uani 1 1 d . . . . .
H26 H 0.7063 0.0888 -0.2051 0.079 Uiso 1 1 calc R U . . .
C28 C 0.9535(2) 0.2962(2) -0.08011(18) 0.0636(6) Uani 1 1 d . . . . .
H28 H 1.0464 0.3136 -0.0825 0.076 Uiso 1 1 calc R U . . .
C33 C 0.0430(2) 0.7026(2) 0.75432(17) 0.0688(7) Uani 1 1 d . . . . .
H33A H 0.1163 0.6478 0.7440 0.083 Uiso 1 1 calc R U . . .
H33B H -0.0248 0.6777 0.7947 0.083 Uiso 1 1 calc R U . . .
C27 C 0.8876(2) 0.1871(2) -0.15635(19) 0.0666(7) Uani 1 1 d . . . . .
H27 H 0.9357 0.1295 -0.2101 0.080 Uiso 1 1 calc R U . . .
C24 C 0.5081(2) 0.2411(2) 0.15654(19) 0.0680(7) Uani 1 1 d . . . . .
H24 H 0.5919 0.2591 0.1990 0.082 Uiso 1 1 calc R U . . .
C21 C 0.2606(3) 0.1860(2) 0.0345(2) 0.0794(7) Uani 1 1 d . . . . .
H21 H 0.1761 0.1674 -0.0069 0.095 Uiso 1 1 calc R U . . .
C5 C 0.7952(3) 0.8227(2) 0.31029(18) 0.0692(7) Uani 1 1 d . . . . .
H5 H 0.8665 0.7721 0.2858 0.083 Uiso 1 1 calc R U . . .
C22 C 0.3109(3) 0.1024(2) 0.0731(2) 0.0764(7) Uani 1 1 d . . . . .
H22 H 0.2610 0.0268 0.0577 0.092 Uiso 1 1 calc R U . . .
C9 C 0.5579(3) 0.8474(2) 0.3187(2) 0.0777(7) Uani 1 1 d . . . . .
H9 H 0.4674 0.8142 0.3010 0.093 Uiso 1 1 calc R U . . .
C32 C -0.1971(3) 0.8261(2) 0.6354(2) 0.0868(8) Uani 1 1 d . . . . .
H32A H -0.1601 0.8916 0.7049 0.130 Uiso 1 1 calc R U . . .
H32B H -0.2944 0.8290 0.6273 0.130 Uiso 1 1 calc R U . . .
H32C H -0.1571 0.8369 0.5737 0.130 Uiso 1 1 calc R U . . .
C23 C 0.4333(3) 0.1295(2) 0.1336(2) 0.0789(7) Uani 1 1 d . . . . .
H23 H 0.4673 0.0726 0.1601 0.095 Uiso 1 1 calc R U . . .
C34 C 0.0997(3) 0.8345(2) 0.82515(19) 0.0971(9) Uani 1 1 d . . . . .
H34A H 0.1667 0.8602 0.7859 0.146 Uiso 1 1 calc R U . . .
H34B H 0.1416 0.8385 0.8953 0.146 Uiso 1 1 calc R U . . .
H34C H 0.0270 0.8889 0.8395 0.146 Uiso 1 1 calc R U . . .
C6 C 0.8243(3) 0.9483(2) 0.3740(2) 0.0941(9) Uani 1 1 d . . . . .
H6 H 0.9146 0.9818 0.3929 0.113 Uiso 1 1 calc R U . . .
C7 C 0.7198(4) 1.0239(3) 0.4097(3) 0.1094(11) Uani 1 1 d . . . . .
H7 H 0.7392 1.1088 0.4528 0.131 Uiso 1 1 calc R U . . .
C8 C 0.5879(4) 0.9744(2) 0.3819(2) 0.1006(10) Uani 1 1 d . . . . .
H8 H 0.5172 1.0259 0.4054 0.121 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
O2 C11 1.374(2) . ?
O2 C14 1.378(2) . ?
N2 C1 1.381(2) . ?
N2 C2 1.393(2) . ?
N2 C10 1.428(2) . ?
N1 C1 1.314(2) . ?
N1 C3 1.385(2) . ?
O1 C11 1.206(2) . ?
N3 C16 1.361(2) . ?
N3 C31 1.459(2) . ?
N3 C33 1.462(2) . ?
C13 C14 1.392(2) . ?
C13 C18 1.398(2) . ?
C13 C12 1.418(2) . ?
C12 C10 1.339(3) . ?
C12 H12 0.9300 . ?
C1 C4 1.469(3) . ?
C10 C11 1.443(3) . ?
C19 C20 1.371(3) . ?
C19 C24 1.382(3) . ?
C19 C2 1.473(3) . ?
C3 C2 1.364(3) . ?
C3 C30 1.473(3) . ?
C14 C15 1.369(2) . ?
C16 C15 1.401(3) . ?
C16 C17 1.418(3) . ?
C17 C18 1.365(2) . ?
C17 H17 0.9300 . ?
C30 C29 1.387(3) . ?
C30 C25 1.390(3) . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C25 C26 1.383(3) . ?
C25 H25 0.9300 . ?
C4 C5 1.377(3) . ?
C4 C9 1.381(3) . ?
C20 C21 1.387(3) . ?
C20 H20 0.9300 . ?
C29 C28 1.380(3) . ?
C29 H29 0.9300 . ?
C31 C32 1.507(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C26 C27 1.365(3) . ?
C26 H26 0.9300 . ?
C28 C27 1.367(3) . ?
C28 H28 0.9300 . ?
C33 C34 1.505(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C27 H27 0.9300 . ?
C24 C23 1.377(3) . ?
C24 H24 0.9300 . ?
C21 C22 1.365(3) . ?
C21 H21 0.9300 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C22 C23 1.349(3) . ?
C22 H22 0.9300 . ?
C9 C8 1.389(3) . ?
C9 H9 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C23 H23 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C6 C7 1.371(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.360(4) . ?
C7 H7 0.9300 . ?
C8 H8 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
C11 O2 C14 122.35(15) . . ?
C1 N2 C2 106.72(15) . . ?
C1 N2 C10 125.83(16) . . ?
C2 N2 C10 123.97(16) . . ?
C1 N1 C3 106.12(16) . . ?
C16 N3 C31 121.64(17) . . ?
C16 N3 C33 121.27(18) . . ?
C31 N3 C33 116.99(16) . . ?
C14 C13 C18 115.60(17) . . ?
C14 C13 C12 118.32(18) . . ?
C18 C13 C12 126.08(18) . . ?
C10 C12 C13 120.55(18) . . ?
C10 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
N1 C1 N2 111.11(17) . . ?
N1 C1 C4 122.80(19) . . ?
N2 C1 C4 126.09(18) . . ?
C12 C10 N2 124.02(17) . . ?
C12 C10 C11 121.73(18) . . ?
N2 C10 C11 114.21(17) . . ?
C20 C19 C24 118.2(2) . . ?
C20 C19 C2 122.51(19) . . ?
C24 C19 C2 119.14(19) . . ?
C2 C3 N1 110.43(17) . . ?
C2 C3 C30 130.21(18) . . ?
N1 C3 C30 119.35(17) . . ?
C15 C14 O2 116.19(17) . . ?
C15 C14 C13 123.38(19) . . ?
O2 C14 C13 120.41(17) . . ?
N3 C16 C15 122.00(18) . . ?
N3 C16 C17 121.02(19) . . ?
C15 C16 C17 116.98(17) . . ?
C18 C17 C16 120.73(19) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C29 C30 C25 117.88(19) . . ?
C29 C30 C3 119.64(19) . . ?
C25 C30 C3 122.47(18) . . ?
C3 C2 N2 105.55(17) . . ?
C3 C2 C19 130.57(18) . . ?
N2 C2 C19 123.68(17) . . ?
C14 C15 C16 120.51(18) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C18 C13 122.79(18) . . ?
C17 C18 H18 118.6 . . ?
C13 C18 H18 118.6 . . ?
C26 C25 C30 119.9(2) . . ?
C26 C25 H25 120.0 . . ?
C30 C25 H25 120.0 . . ?
C5 C4 C9 118.4(2) . . ?
C5 C4 C1 118.2(2) . . ?
C9 C4 C1 123.3(2) . . ?
C19 C20 C21 120.4(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C28 C29 C30 121.5(2) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
N3 C31 C32 114.17(18) . . ?
N3 C31 H31A 108.7 . . ?
C32 C31 H31A 108.7 . . ?
N3 C31 H31B 108.7 . . ?
C32 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
O1 C11 O2 117.97(19) . . ?
O1 C11 C10 125.50(19) . . ?
O2 C11 C10 116.52(18) . . ?
C27 C26 C25 121.2(2) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C27 C28 C29 119.9(2) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
N3 C33 C34 114.00(19) . . ?
N3 C33 H33A 108.8 . . ?
C34 C33 H33A 108.8 . . ?
N3 C33 H33B 108.8 . . ?
C34 C33 H33B 108.8 . . ?
H33A C33 H33B 107.6 . . ?
C26 C27 C28 119.6(2) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C23 C24 C19 120.8(2) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C23 C22 C21 119.9(2) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C4 C9 C8 120.1(3) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C22 C23 C24 120.4(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.035



