# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1919849'
loop_
_audit_author_name
_audit_author_address
'Ferdi Karadas'
;Bilkent University
Turkey
;
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_audit_creation_date             2018-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_systematic        Crystal
_chemical_formula_moiety         'C23 H23 N5 O5'
_chemical_formula_sum            'C23 H23 N5 O5'
_chemical_formula_weight         449.47
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   10.2450(2)
_cell_length_b                   10.9607(2)
_cell_length_c                   11.1338(7)
_cell_angle_alpha                74.014(5)
_cell_angle_beta                 74.695(5)
_cell_angle_gamma                72.702(5)
_cell_volume                     1124.73(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    29145
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      28.26
_cell_measurement_temperature    295
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.3271
_exptl_crystal_description       block
_exptl_crystal_F_000             472.2417
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.76
_exptl_crystal_size_min          0.55
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29145
_diffrn_reflns_theta_full        28.2574
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         3.07
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9969
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku RAXIS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                4872
_reflns_number_total             5552
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.3754
_refine_diff_density_min         -0.4439
_refine_diff_density_rms         0.1277
_refine_ls_d_res_high            0.7506
_refine_ls_d_res_low             6.6456
_refine_ls_goodness_of_fit_ref   1.0697
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5552
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0588
_refine_ls_restrained_S_all      1.0697
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0973P)²+0.1929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1599
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C16(H16), C15(H15), C14(H14), C13(H13), N2(H2)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C23(H23a,H23b,H23c), C22(H22a,H22b,H22c), C21(H21a,H21b,H21c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O5 O 0.06874(10) 0.01362(9) 0.78766(10) 0.0450(2) Uani 1.000000 .
O1 O -0.23712(11) 0.35964(10) 0.79541(9) 0.0481(2) Uani 1.000000 .
O3 O -0.36837(12) 0.05620(9) 0.84692(10) 0.0540(3) Uani 1.000000 .
O2 O -0.49148(11) 0.43538(9) 0.65918(10) 0.0523(3) Uani 1.000000 .
O4 O 0.07340(12) 0.21188(10) 0.65296(11) 0.0573(3) Uani 1.000000 .
N5 N -0.2744(3) -0.10897(17) 0.6408(2) 0.1039(8) Uani 1.000000 .
N2 N -0.10849(12) 0.11922(9) 0.69168(11) 0.0401(2) Uani 1.000000 .
H2 H -0.13632(12) 0.04797(9) 0.71953(11) 0.0481(3) Uiso 1.000000 R
N1 N -0.19563(12) 0.46050(10) 0.58252(10) 0.0405(2) Uani 1.000000 .
N4 N -0.30418(14) -0.00055(12) 0.61832(14) 0.0539(3) Uani 1.000000 .
N3 N -0.33961(17) 0.11721(13) 0.57565(12) 0.0557(3) Uani 1.000000 .
C22 C 0.1953(3) 0.0983(2) 0.8920(2) 0.0782(6) Uani 1.000000 .
H22a H 0.190(2) 0.1805(4) 0.8319(4) 0.1173(9) Uiso 1.000000 GR
H22b H 0.1137(11) 0.1045(12) 0.9588(12) 0.1173(9) Uiso 1.000000 GR
H22c H 0.2769(9) 0.0768(9) 0.9279(15) 0.1173(9) Uiso 1.000000 GR
C15 C -0.6527(2) 0.3369(2) 1.04472(18) 0.0708(5) Uani 1.000000 .
H15 H -0.6932(2) 0.3163(2) 1.13061(18) 0.0850(6) Uiso 1.000000 R
C14 C -0.6763(2) 0.4668(2) 0.9784(2) 0.0764(5) Uani 1.000000 .
H14 H -0.7287(2) 0.5327(2) 1.0215(2) 0.0917(6) Uiso 1.000000 R
C21 C 0.3206(2) -0.0143(3) 0.7103(2) 0.0968(8) Uani 1.000000 .
H21a H 0.3137(14) -0.0745(17) 0.6652(12) 0.1452(13) Uiso 1.000000 GR
H21b H 0.3143(14) 0.0708(5) 0.6551(11) 0.1452(13) Uiso 1.000000 GR
H21c H 0.4085(2) -0.044(2) 0.7374(3) 0.1452(13) Uiso 1.000000 GR
C3 C -0.19598(13) 0.23723(11) 0.62809(11) 0.0353(2) Uani 1.000000 .
C2 C -0.21177(13) 0.35819(11) 0.68281(12) 0.0371(3) Uani 1.000000 .
C18 C -0.40799(14) 0.16928(12) 0.79126(12) 0.0406(3) Uani 1.000000 .
C4 C -0.14027(13) 0.28504(12) 0.48800(12) 0.0381(3) Uani 1.000000 .
C10 C -0.34610(13) 0.21269(11) 0.64862(11) 0.0379(3) Uani 1.000000 .
C9 C -0.14952(13) 0.41901(12) 0.46658(12) 0.0394(3) Uani 1.000000 .
C19 C 0.01806(14) 0.12291(12) 0.70660(12) 0.0397(3) Uani 1.000000 .
C17 C -0.51122(14) 0.26934(13) 0.85295(13) 0.0428(3) Uani 1.000000 .
C12 C -0.54248(14) 0.39964(14) 0.78681(14) 0.0476(3) Uani 1.000000 .
C11 C -0.45185(15) 0.33270(14) 0.59234(13) 0.0483(3) Uani 1.000000 .
H11a H -0.53452(15) 0.30624(14) 0.59334(13) 0.0579(4) Uiso 1.000000 R
H11b H -0.41187(15) 0.36530(14) 0.50416(13) 0.0579(4) Uiso 1.000000 R
C5 C -0.08766(16) 0.22110(15) 0.38852(14) 0.0492(3) Uani 1.000000 .
H5 H -0.08016(16) 0.13188(15) 0.40222(14) 0.0590(4) Uiso 1.000000 R
C20 C 0.20354(15) -0.00724(15) 0.82510(14) 0.0501(3) Uani 1.000000 .
C8 C -0.11110(16) 0.49239(15) 0.34555(14) 0.0513(3) Uani 1.000000 .
H8 H -0.11971(16) 0.58185(15) 0.33136(14) 0.0615(4) Uiso 1.000000 R
C16 C -0.56981(17) 0.23907(17) 0.98357(14) 0.0530(3) Uani 1.000000 .
H16 H -0.55245(17) 0.15271(17) 1.02867(14) 0.0636(4) Uiso 1.000000 R
C1 C -0.22632(17) 0.59467(13) 0.59677(16) 0.0509(3) Uani 1.000000 .
H1a H -0.3128(7) 0.6429(3) 0.5706(12) 0.0763(5) Uiso 1.000000 GR
H1b H -0.2338(13) 0.59523(14) 0.6844(3) 0.0763(5) Uiso 1.000000 GR
H1c H -0.1526(7) 0.6345(4) 0.5447(10) 0.0763(5) Uiso 1.000000 GR
C6 C -0.04582(18) 0.2929(2) 0.26670(15) 0.0609(4) Uani 1.000000 .
H6 H -0.00874(18) 0.2510(2) 0.19868(15) 0.0731(5) Uiso 1.000000 R
C7 C -0.05908(19) 0.42564(19) 0.24651(14) 0.0614(4) Uani 1.000000 .
H7 H -0.03245(19) 0.47189(19) 0.16425(14) 0.0737(5) Uiso 1.000000 R
C23 C 0.2139(2) -0.13838(18) 0.9189(2) 0.0726(5) Uani 1.000000 .
H23a H 0.1362(10) -0.1318(5) 0.9893(8) 0.1088(8) Uiso 1.000000 GR
H23b H 0.2127(18) -0.2037(4) 0.8770(5) 0.1088(8) Uiso 1.000000 GR
H23c H 0.2992(9) -0.1625(8) 0.9495(13) 0.1088(8) Uiso 1.000000 GR
C13 C -0.6228(2) 0.49868(17) 0.8498(2) 0.0659(4) Uani 1.000000 .
H13 H -0.6402(2) 0.58539(17) 0.8056(2) 0.0791(5) Uiso 1.000000 R


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
O5 C19 1.3420(14) . ?
O5 C20 1.4821(15) . ?
O1 C2 1.2149(16) . ?
O3 C18 1.2229(15) . ?
O2 C12 1.3670(18) . ?
O2 C11 1.4196(19) . ?
O4 C19 1.2076(16) . ?
N5 N4 1.109(2) . ?
N2 H2 0.8600 . ?
N2 C3 1.4556(14) . ?
N2 C19 1.3634(16) . ?
N1 C2 1.3619(15) . ?
N1 C9 1.4035(17) . ?
N1 C1 1.4539(16) . ?
N4 N3 1.2240(18) . ?
N3 C10 1.4691(17) . ?
C22 H22a 0.9600 . ?
C22 H22b 0.9600 . ?
C22 H22c 0.9600 . ?
C22 C20 1.511(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.393(3) . ?
C15 C16 1.375(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.378(3) . ?
C21 H21a 0.9600 . ?
C21 H21b 0.9600 . ?
C21 H21c 0.9600 . ?
C21 C20 1.506(3) . ?
C3 C2 1.5558(16) . ?
C3 C4 1.5135(16) . ?
C3 C10 1.5863(17) . ?
C18 C10 1.5434(17) . ?
C18 C17 1.461(2) . ?
C4 C9 1.3994(17) . ?
C4 C5 1.3771(19) . ?
C10 C11 1.5342(17) . ?
C9 C8 1.3889(18) . ?
C17 C12 1.3992(18) . ?
C17 C16 1.406(2) . ?
C12 C13 1.389(2) . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C5 H5 0.9300 . ?
C5 C6 1.396(2) . ?
C20 C23 1.519(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.392(2) . ?
C16 H16 0.9300 . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C6 H6 0.9300 . ?
C6 C7 1.380(3) . ?
C7 H7 0.9300 . ?
C23 H23a 0.9600 . ?
C23 H23b 0.9600 . ?
C23 H23c 0.9600 . ?
C13 H13 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
C20 O5 C19 121.25(10) . . ?
C11 O2 C12 114.55(11) . . ?
C3 N2 H2 120.37(6) . . ?
C19 N2 H2 120.37(6) . . ?
C19 N2 C3 119.26(10) . . ?
C9 N1 C2 111.17(10) . . ?
C1 N1 C2 123.19(12) . . ?
C1 N1 C9 125.63(11) . . ?
N3 N4 N5 169.95(19) . . ?
C10 N3 N4 121.25(12) . . ?
H22b C22 H22a 109.5 . . ?
H22c C22 H22a 109.5 . . ?
H22c C22 H22b 109.5 . . ?
C20 C22 H22a 109.5 . . ?
C20 C22 H22b 109.5 . . ?
C20 C22 H22c 109.5 . . ?
C14 C15 H15 119.89(11) . . ?
C16 C15 H15 119.89(11) . . ?
C16 C15 C14 120.22(17) . . ?
H14 C14 C15 119.64(11) . . ?
C13 C14 C15 120.72(18) . . ?
C13 C14 H14 119.64(12) . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?
C20 C21 H21a 109.5 . . ?
C20 C21 H21b 109.5 . . ?
C20 C21 H21c 109.5 . . ?
C2 C3 N2 112.25(9) . . ?
C4 C3 N2 115.69(10) . . ?
C4 C3 C2 101.54(9) . . ?
C10 C3 N2 108.07(9) . . ?
C10 C3 C2 108.44(10) . . ?
C10 C3 C4 110.59(9) . . ?
N1 C2 O1 127.06(11) . . ?
C3 C2 O1 125.17(11) . . ?
C3 C2 N1 107.74(10) . . ?
C10 C18 O3 119.73(12) . . ?
C17 C18 O3 123.55(12) . . ?
C17 C18 C10 116.71(10) . . ?
C9 C4 C3 108.15(10) . . ?
C5 C4 C3 131.66(11) . . ?
C5 C4 C9 120.19(12) . . ?
C3 C10 N3 109.94(11) . . ?
C18 C10 N3 111.58(10) . . ?
C18 C10 C3 111.67(9) . . ?
C11 C10 N3 102.00(11) . . ?
C11 C10 C3 113.56(10) . . ?
C11 C10 C18 107.72(11) . . ?
C4 C9 N1 110.11(10) . . ?
C8 C9 N1 128.00(12) . . ?
C8 C9 C4 121.84(13) . . ?
O4 C19 O5 126.83(12) . . ?
N2 C19 O5 109.34(10) . . ?
N2 C19 O4 123.82(11) . . ?
C12 C17 C18 120.61(12) . . ?
C16 C17 C18 120.41(12) . . ?
C16 C17 C12 118.64(14) . . ?
C17 C12 O2 121.64(13) . . ?
C13 C12 O2 117.33(13) . . ?
C13 C12 C17 120.99(15) . . ?
C10 C11 O2 113.32(11) . . ?
H11a C11 O2 108.91(7) . . ?
H11a C11 C10 108.91(7) . . ?
H11b C11 O2 108.91(7) . . ?
H11b C11 C10 108.91(7) . . ?
H11b C11 H11a 107.7 . . ?
H5 C5 C4 120.67(8) . . ?
C6 C5 C4 118.66(14) . . ?
C6 C5 H5 120.67(10) . . ?
C22 C20 O5 109.80(13) . . ?
C21 C20 O5 110.06(13) . . ?
C21 C20 C22 112.94(19) . . ?
C23 C20 O5 102.15(12) . . ?
C23 C20 C22 110.01(15) . . ?
C23 C20 C21 111.34(18) . . ?
H8 C8 C9 121.59(9) . . ?
C7 C8 C9 116.82(14) . . ?
C7 C8 H8 121.59(9) . . ?
C17 C16 C15 120.12(16) . . ?
H16 C16 C15 119.94(11) . . ?
H16 C16 C17 119.94(9) . . ?
H1a C1 N1 109.5 . . ?
H1b C1 N1 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 N1 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
H6 C6 C5 119.77(10) . . ?
C7 C6 C5 120.45(15) . . ?
C7 C6 H6 119.77(9) . . ?
C6 C7 C8 121.99(14) . . ?
H7 C7 C8 119.01(9) . . ?
H7 C7 C6 119.01(9) . . ?
H23a C23 C20 109.5 . . ?
H23b C23 C20 109.5 . . ?
H23b C23 H23a 109.5 . . ?
H23c C23 C20 109.5 . . ?
H23c C23 H23a 109.5 . . ?
H23c C23 H23b 109.5 . . ?
C12 C13 C14 119.17(17) . . ?
H13 C13 C14 120.41(11) . . ?
H13 C13 C12 120.41(10) . . ?

_olex2_submission_original_sample_id Seda
_olex2_submission_special_instructions 'No special instructions were received'
