# Electronic Supplementary Material (ESI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 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_nhpdi
_database_code_depnum_ccdc_archive 'CCDC 2003001'
loop_
_audit_author_name
_audit_author_address
'Benjamin Gelfand'
;University of Calgary
Canada
;
_audit_update_record             
;
2020-05-10 deposited with the CCDC.	2020-08-20 downloaded from the CCDC.
;
_audit_creation_date             2020-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H29 N3 O4'
_chemical_formula_sum            'C34 H29 N3 O4'
_chemical_formula_weight         543.60
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.2166(7)
_cell_length_b                   18.5973(10)
_cell_length_c                   7.8095(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.881(2)
_cell_angle_gamma                90
_cell_volume                     2620.71(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    173
_cell_measurement_theta_max      65.132
_cell_measurement_theta_min      3.413
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.779
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0995 before and 0.0345 after correction. The Ratio of minimum to maximum transmission is 0.8787. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.086
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22039
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        65.226
_diffrn_reflns_theta_max         65.226
_diffrn_reflns_theta_min         2.449
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3893
_reflns_number_total             4467
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         4467
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0847P)²+2.2686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1639
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C27(H27), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C28(H28A,H28B), C33(H33A,H33B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C11(H11), C12(H12), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C29(H29A,H29B,H29C), C34(H34A,H34B,H34C), C30(H30A,H30B,
 H30C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.60916(9) 0.76901(9) 0.1142(2) 0.0476(4) Uani 1 1 d . . . . .
O2 O 0.11347(10) 0.96510(10) 0.5426(3) 0.0608(5) Uani 1 1 d . . . . .
O3 O 0.02675(11) 0.74746(12) 0.6838(3) 0.0643(6) Uani 1 1 d . . . . .
O4 O 0.56941(11) 0.53286(9) 0.2319(3) 0.0566(5) Uani 1 1 d . . . . .
N1 N 0.59021(11) 0.65053(10) 0.1739(2) 0.0397(5) Uani 1 1 d . . . . .
N2 N 0.37424(10) 0.89498(10) 0.3374(2) 0.0322(4) Uani 1 1 d . . . . .
H2 H 0.3881(14) 0.9399(15) 0.322(3) 0.040(7) Uiso 1 1 d . . . . .
N3 N 0.06502(10) 0.85509(11) 0.5915(3) 0.0424(5) Uani 1 1 d . . . . .
C1 C 0.56996(13) 0.72443(12) 0.1703(3) 0.0368(5) Uani 1 1 d . . . . .
C2 C 0.50048(12) 0.74364(11) 0.2354(3) 0.0325(5) Uani 1 1 d . . . . .
C3 C 0.48083(12) 0.81625(11) 0.2414(3) 0.0320(5) Uani 1 1 d . . . . .
H3 H 0.510998 0.852925 0.203004 0.038 Uiso 1 1 calc R . . . .
C4 C 0.41412(12) 0.83280(11) 0.3072(3) 0.0304(5) Uani 1 1 d . . . . .
C5 C 0.30878(12) 0.87538(11) 0.4026(3) 0.0319(5) Uani 1 1 d . . . . .
C6 C 0.24542(12) 0.90953(12) 0.4513(3) 0.0329(5) Uani 1 1 d . . . . .
H6 H 0.240695 0.960408 0.448574 0.039 Uiso 1 1 calc R . . . .
C7 C 0.19019(12) 0.86620(12) 0.5033(3) 0.0330(5) Uani 1 1 d . . . . .
C8 C 0.12148(13) 0.90048(14) 0.5464(3) 0.0414(6) Uani 1 1 d . . . . .
C9 C 0.07318(13) 0.78180(15) 0.6185(3) 0.0457(6) Uani 1 1 d . . . . .
C10 C 0.13935(13) 0.74671(13) 0.5666(3) 0.0388(5) Uani 1 1 d . . . . .
C11 C 0.14894(13) 0.67291(13) 0.5689(3) 0.0415(6) Uani 1 1 d . . . . .
H11 H 0.112011 0.643634 0.608681 0.050 Uiso 1 1 calc R . . . .
C12 C 0.21041(13) 0.63978(12) 0.5155(3) 0.0397(5) Uani 1 1 d . . . . .
H12 H 0.213272 0.588770 0.516711 0.048 Uiso 1 1 calc R . . . .
C13 C 0.26835(12) 0.67944(12) 0.4599(3) 0.0349(5) Uani 1 1 d . . . . .
C14 C 0.33769(13) 0.65236(11) 0.4017(3) 0.0358(5) Uani 1 1 d . . . . .
C15 C 0.36067(14) 0.58130(12) 0.3960(3) 0.0404(5) Uani 1 1 d . . . . .
H15 H 0.329860 0.544158 0.429825 0.048 Uiso 1 1 calc R . . . .
C16 C 0.42831(14) 0.56347(12) 0.3416(3) 0.0419(6) Uani 1 1 d . . . . .
H16 H 0.442186 0.514221 0.341880 0.050 Uiso 1 1 calc R . . . .
C17 C 0.47672(13) 0.61439(11) 0.2867(3) 0.0360(5) Uani 1 1 d . . . . .
C18 C 0.54749(14) 0.59511(12) 0.2306(3) 0.0415(6) Uani 1 1 d . . . . .
C19 C 0.45593(12) 0.68666(11) 0.2887(3) 0.0328(5) Uani 1 1 d . . . . .
C20 C 0.38831(12) 0.70314(11) 0.3472(3) 0.0319(5) Uani 1 1 d . . . . .
C21 C 0.37317(12) 0.77578(11) 0.3541(3) 0.0315(5) Uani 1 1 d . . . . .
C22 C 0.30993(12) 0.80078(11) 0.4117(3) 0.0318(5) Uani 1 1 d . . . . .
C23 C 0.25720(12) 0.75549(12) 0.4628(3) 0.0334(5) Uani 1 1 d . . . . .
C24 C 0.19496(12) 0.78952(12) 0.5116(3) 0.0331(5) Uani 1 1 d . . . . .
C25 C 0.74677(19) 0.6655(2) 0.3827(5) 0.0897(13) Uani 1 1 d . . . . .
H25A H 0.767943 0.705676 0.324529 0.134 Uiso 1 1 calc GR . . . .
H25B H 0.784740 0.645114 0.470213 0.134 Uiso 1 1 calc GR . . . .
H25C H 0.705089 0.682865 0.438404 0.134 Uiso 1 1 calc GR . . . .
C26 C 0.71966(17) 0.60804(19) 0.2506(4) 0.0683(9) Uani 1 1 d . . . . .
H26A H 0.762589 0.589927 0.198225 0.082 Uiso 1 1 calc R . . . .
H26B H 0.699702 0.567319 0.311589 0.082 Uiso 1 1 calc R . . . .
C27 C 0.66139(14) 0.63248(14) 0.1089(3) 0.0462(6) Uani 1 1 d . . . . .
H27 H 0.680043 0.679205 0.068361 0.055 Uiso 1 1 calc R . . . .
C28 C 0.64985(15) 0.58455(16) -0.0520(4) 0.0561(7) Uani 1 1 d . . . . .
H28A H 0.647490 0.533681 -0.015764 0.067 Uiso 1 1 calc R . . . .
H28B H 0.601906 0.596787 -0.121624 0.067 Uiso 1 1 calc R . . . .
C29 C 0.71110(19) 0.59310(16) -0.1622(4) 0.0622(8) Uani 1 1 d . . . . .
H29A H 0.699622 0.564426 -0.267724 0.093 Uiso 1 1 calc GR . . . .
H29B H 0.757973 0.576577 -0.097478 0.093 Uiso 1 1 calc GR . . . .
H29C H 0.715516 0.643858 -0.192900 0.093 Uiso 1 1 calc GR . . . .
C32 C -0.00622(13) 0.89141(16) 0.6226(3) 0.0496(6) Uani 1 1 d . . . . .
H32 H -0.001828 0.941992 0.581726 0.060 Uiso 1 1 calc R . . . .
C33 C -0.01192(18) 0.8977(2) 0.8123(4) 0.0711(9) Uani 1 1 d . . . . .
H33A H -0.024270 0.849845 0.856121 0.085 Uiso 1 1 calc R . . . .
H33B H 0.037056 0.911841 0.874000 0.085 Uiso 1 1 calc R . . . .
C34 C -0.06881(16) 0.9509(2) 0.8541(4) 0.0729(10) Uani 1 1 d . . . . .
H34A H -0.117562 0.937526 0.793354 0.109 Uiso 1 1 calc GR . . . .
H34B H -0.055572 0.999044 0.817207 0.109 Uiso 1 1 calc GR . . . .
H34C H -0.070421 0.951023 0.979006 0.109 Uiso 1 1 calc GR . . . .
C31 C -0.07268(17) 0.8606(2) 0.5086(5) 0.0763(10) Uani 1 1 d . . . . .
H31A H -0.074214 0.808144 0.529150 0.092 Uiso 1 1 calc R . . . .
H31B H -0.118098 0.881641 0.544658 0.092 Uiso 1 1 calc R . . . .
C30 C -0.0743(2) 0.8730(3) 0.3210(5) 0.1077(17) Uani 1 1 d . . . . .
H30A H -0.115941 0.846492 0.257428 0.162 Uiso 1 1 calc GR . . . .
H30B H -0.027809 0.856111 0.285080 0.162 Uiso 1 1 calc GR . . . .
H30C H -0.080323 0.924450 0.296305 0.162 Uiso 1 1 calc GR . . . .


_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 1.215(3) . ?
O2 C8 1.210(3) . ?
O3 C9 1.225(3) . ?
O4 C18 1.224(3) . ?
N1 C1 1.422(3) . ?
N1 C18 1.399(3) . ?
N1 C27 1.494(3) . ?
N2 C4 1.403(3) . ?
N2 C5 1.407(3) . ?
N3 C8 1.412(3) . ?
N3 C9 1.384(3) . ?
N3 C32 1.512(3) . ?
C1 C2 1.471(3) . ?
C2 C3 1.399(3) . ?
C2 C19 1.431(3) . ?
C3 C4 1.416(3) . ?
C4 C21 1.375(3) . ?
C5 C6 1.414(3) . ?
C5 C22 1.389(3) . ?
C6 C7 1.392(3) . ?
C7 C8 1.484(3) . ?
C7 C24 1.430(3) . ?
C9 C10 1.476(4) . ?
C10 C11 1.383(3) . ?
C10 C24 1.401(3) . ?
C11 C12 1.391(4) . ?
C12 C13 1.404(3) . ?
C13 C14 1.488(3) . ?
C13 C23 1.430(3) . ?
C14 C15 1.389(3) . ?
C14 C20 1.425(3) . ?
C15 C16 1.397(4) . ?
C16 C17 1.401(3) . ?
C17 C18 1.462(3) . ?
C17 C19 1.397(3) . ?
C19 C20 1.405(3) . ?
C20 C21 1.381(3) . ?
C21 C22 1.374(3) . ?
C22 C23 1.377(3) . ?
C23 C24 1.396(3) . ?
C25 C26 1.520(5) . ?
C26 C27 1.496(4) . ?
C27 C28 1.531(4) . ?
C28 C29 1.508(4) . ?
C32 C33 1.504(4) . ?
C32 C31 1.513(4) . ?
C33 C34 1.502(4) . ?
C31 C30 1.479(5) . ?

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
C1 N1 C27 116.4(2) . . ?
C18 N1 C1 124.3(2) . . ?
C18 N1 C27 119.23(19) . . ?
C4 N2 C5 109.36(17) . . ?
C8 N3 C32 116.3(2) . . ?
C9 N3 C8 124.1(2) . . ?
C9 N3 C32 119.5(2) . . ?
O1 C1 N1 120.2(2) . . ?
O1 C1 C2 122.3(2) . . ?
N1 C1 C2 117.5(2) . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 C19 123.2(2) . . ?
C19 C2 C1 118.02(19) . . ?
C2 C3 C4 117.25(19) . . ?
N2 C4 C3 136.88(19) . . ?
C21 C4 N2 106.17(19) . . ?
C21 C4 C3 116.94(19) . . ?
N2 C5 C6 138.1(2) . . ?
C22 C5 N2 105.65(18) . . ?
C22 C5 C6 116.21(19) . . ?
C7 C6 C5 117.87(19) . . ?
C6 C7 C8 118.9(2) . . ?
C6 C7 C24 123.3(2) . . ?
C24 C7 C8 117.8(2) . . ?
O2 C8 N3 120.7(2) . . ?
O2 C8 C7 121.6(2) . . ?
N3 C8 C7 117.7(2) . . ?
O3 C9 N3 120.7(2) . . ?
O3 C9 C10 121.4(3) . . ?
N3 C9 C10 117.9(2) . . ?
C11 C10 C9 122.8(2) . . ?
C11 C10 C24 118.2(2) . . ?
C24 C10 C9 119.0(2) . . ?
C10 C11 C12 122.7(2) . . ?
C11 C12 C13 122.0(2) . . ?
C12 C13 C14 128.5(2) . . ?
C12 C13 C23 113.6(2) . . ?
C23 C13 C14 117.91(19) . . ?
C15 C14 C13 127.2(2) . . ?
C15 C14 C20 114.3(2) . . ?
C20 C14 C13 118.56(19) . . ?
C14 C15 C16 121.2(2) . . ?
C15 C16 C17 123.4(2) . . ?
C16 C17 C18 123.0(2) . . ?
C19 C17 C16 117.6(2) . . ?
C19 C17 C18 119.4(2) . . ?
O4 C18 N1 120.3(2) . . ?
O4 C18 C17 122.0(2) . . ?
N1 C18 C17 117.8(2) . . ?
C17 C19 C2 122.9(2) . . ?
C17 C19 C20 117.7(2) . . ?
C20 C19 C2 119.38(19) . . ?
C19 C20 C14 125.8(2) . . ?
C21 C20 C14 119.7(2) . . ?
C21 C20 C19 114.5(2) . . ?
C4 C21 C20 128.7(2) . . ?
C22 C21 C4 109.65(19) . . ?
C22 C21 C20 121.6(2) . . ?
C21 C22 C5 109.18(19) . . ?
C21 C22 C23 122.5(2) . . ?
C23 C22 C5 128.3(2) . . ?
C22 C23 C13 119.6(2) . . ?
C22 C23 C24 115.3(2) . . ?
C24 C23 C13 125.1(2) . . ?
C10 C24 C7 122.6(2) . . ?
C23 C24 C7 119.09(19) . . ?
C23 C24 C10 118.3(2) . . ?
C27 C26 C25 114.8(3) . . ?
N1 C27 C26 112.2(2) . . ?
N1 C27 C28 112.4(2) . . ?
C26 C27 C28 115.7(2) . . ?
C29 C28 C27 112.2(2) . . ?
N3 C32 C31 111.8(2) . . ?
C33 C32 N3 111.7(2) . . ?
C33 C32 C31 116.8(3) . . ?
C34 C33 C32 114.1(2) . . ?
C30 C31 C32 115.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dioxane, methanol'
