# 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_compound_8
_database_code_depnum_ccdc_archive 'CCDC 1915359'
loop_
_audit_author_name
_audit_author_address
'Christian Jandl'
;Technische Universitaet Muenchen
Germany
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 N O4'
_chemical_formula_structural     ?
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         315.36
_chemical_compound_source        'see text'

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   17.209(3)
_cell_length_b                   5.0340(8)
_cell_length_c                   19.434(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.812(5)
_cell_angle_gamma                90
_cell_volume                     1627.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    6968
_cell_measurement_theta_min      2.4484
_cell_measurement_theta_max      25.6309
_cell_special_details            
;
;

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.811
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.077
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.091
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5, Bruker, 2014'
_exptl_absorpt_correction_T_min  0.5933
_exptl_absorpt_correction_T_max  0.7453

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             C. Jandl
scanspeed                           60 s per frame
dx                                  40 mm
1364 frames measured in 9 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
;
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_monochromator  'Helios optic'

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker Photon CMOS '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CMOS plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            32123
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2946
# number of observed reflections (> n sig(I))
_reflns_number_gt                2185
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX III Control Software (Bruker, 2015)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL2014 (Sheldrick, 2014), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2014)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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     
'W=1/[Σ²(FO²)+(0.0548P)²+1.1721P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom


_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         2946
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.052

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.96080(10) 0.3490(3) 0.60476(9) 1.000 0.0356(6) d . . .
O2 O Uani 0.93310(9) 0.7137(3) 0.65115(8) 1.000 0.0316(5) d . . .
O3 O Uani 0.51583(9) -0.0920(3) 0.60689(9) 1.000 0.0355(5) d . . .
O4 O Uani 0.61612(9) -0.1444(3) 0.70444(8) 1.000 0.0287(5) d . . .
N1 N Uani 0.92197(10) 0.5533(4) 0.60247(10) 1.000 0.0232(6) d . . .
C1 C Uani 0.85922(12) 0.6125(4) 0.53443(11) 1.000 0.0211(6) d . . .
C2 C Uani 0.89191(13) 0.8160(5) 0.49098(12) 1.000 0.0266(7) d . . .
C3 C Uani 0.81654(13) 0.9387(4) 0.44349(11) 1.000 0.0247(7) d . . .
C4 C Uani 0.74525(13) 0.8720(4) 0.47299(11) 1.000 0.0241(7) d . . .
C5 C Uani 0.78234(12) 0.7401(4) 0.54618(11) 1.000 0.0204(6) d . . .
C6 C Uani 0.72817(12) 0.5464(4) 0.57172(10) 1.000 0.0192(6) d . . .
C7 C Uani 0.65173(12) 0.4781(4) 0.52922(11) 1.000 0.0203(6) d . . .
C8 C Uani 0.61882(13) 0.6036(5) 0.45709(12) 1.000 0.0282(7) d . . .
C9 C Uani 0.68577(13) 0.6863(5) 0.42362(11) 1.000 0.0270(7) d . . .
C10 C Uani 0.75484(12) 0.4300(4) 0.63907(11) 1.000 0.0216(6) d . . .
C11 C Uani 0.70933(12) 0.2423(5) 0.66287(11) 1.000 0.0220(6) d . . .
C12 C Uani 0.63463(12) 0.1678(4) 0.61978(11) 1.000 0.0192(6) d . . .
C13 C Uani 0.60647(12) 0.2897(4) 0.55396(11) 1.000 0.0204(6) d . . .
C14 C Uani 0.81172(15) 1.0795(5) 0.38458(12) 1.000 0.0304(8) d . . .
C15 C Uani 0.87894(15) 1.1493(6) 0.35265(13) 1.000 0.0379(8) d . . .
C16 C Uani 0.86427(19) 1.0575(9) 0.27635(15) 1.000 0.0658(13) d . . .
C17 C Uani 0.58236(12) -0.0327(4) 0.64145(11) 1.000 0.0211(6) d . . .
C18 C Uani 0.56686(15) -0.3352(5) 0.72944(13) 1.000 0.0337(8) d . . .
H1 H Uiso 0.84510 0.44540 0.50620 1.000 0.0250 c RU . .
H2A H Uiso 0.92500 0.95150 0.52220 1.000 0.0320 c RU . .
H2B H Uiso 0.92480 0.72930 0.46240 1.000 0.0320 c RU . .
H4 H Uiso 0.71710 1.03950 0.48020 1.000 0.0290 c RU . .
H5 H Uiso 0.79840 0.88360 0.58260 1.000 0.0250 c RU . .
H8A H Uiso 0.58640 0.76140 0.46210 1.000 0.0340 c RU . .
H8B H Uiso 0.58310 0.47540 0.42540 1.000 0.0340 c RU . .
H9A H Uiso 0.66240 0.77760 0.37790 1.000 0.0320 c RU . .
H9B H Uiso 0.71450 0.52630 0.41360 1.000 0.0320 c RU . .
H10 H Uiso 0.80530 0.48130 0.66900 1.000 0.0260 c RU . .
H11 H Uiso 0.72890 0.16400 0.70850 1.000 0.0260 c RU . .
H13 H Uiso 0.55490 0.24290 0.52510 1.000 0.0240 c RU . .
H14 H Uiso 0.75990 1.14200 0.36030 1.000 0.0370 c RU . .
H15A H Uiso 0.92910 1.06740 0.38130 1.000 0.0450 c RU . .
H15B H Uiso 0.88640 1.34440 0.35450 1.000 0.0450 c RU . .
H16A H Uiso 0.81240 1.12590 0.24860 1.000 0.0990 c RU . .
H16B H Uiso 0.86360 0.86290 0.27480 1.000 0.0990 c RU . .
H16C H Uiso 0.90720 1.12410 0.25620 1.000 0.0990 c RU . .
H18A H Uiso 0.52090 -0.24410 0.74000 1.000 0.0510 c RU . .
H18B H Uiso 0.59880 -0.42140 0.77270 1.000 0.0510 c RU . .
H18C H Uiso 0.54740 -0.46960 0.69260 1.000 0.0510 c RU . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.221(3) . . yes
O2 N1 1.221(2) . . yes
O3 C17 1.207(3) . . yes
O4 C17 1.337(3) . . yes
O4 C18 1.445(3) . . yes
N1 C1 1.508(3) . . yes
C1 C2 1.524(3) . . no
C1 C5 1.539(3) . . no
C2 C3 1.518(3) . . no
C3 C4 1.519(3) . . no
C3 C14 1.331(3) . . no
C4 C5 1.552(3) . . no
C4 C9 1.530(3) . . no
C5 C6 1.518(3) . . no
C6 C7 1.406(3) . . no
C6 C10 1.400(3) . . no
C7 C8 1.510(3) . . no
C7 C13 1.389(3) . . no
C8 C9 1.519(3) . . no
C10 C11 1.380(3) . . no
C11 C12 1.394(3) . . no
C12 C13 1.390(3) . . no
C12 C17 1.483(3) . . no
C14 C15 1.488(4) . . no
C15 C16 1.512(4) . . no
C1 H1 1.0000 . . no
C2 H2A 0.9900 . . no
C2 H2B 0.9900 . . no
C4 H4 1.0000 . . no
C5 H5 1.0000 . . no
C8 H8A 0.9900 . . no
C8 H8B 0.9900 . . no
C9 H9A 0.9900 . . no
C9 H9B 0.9900 . . no
C10 H10 0.9500 . . no
C11 H11 0.9500 . . no
C13 H13 0.9500 . . no
C14 H14 0.9500 . . no
C15 H15A 0.9900 . . no
C15 H15B 0.9900 . . no
C16 H16A 0.9800 . . no
C16 H16B 0.9800 . . no
C16 H16C 0.9800 . . no
C18 H18A 0.9800 . . no
C18 H18B 0.9800 . . no
C18 H18C 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O4 C18 115.62(17) . . . yes
O1 N1 O2 123.55(19) . . . yes
O1 N1 C1 117.45(18) . . . yes
O2 N1 C1 118.95(18) . . . yes
N1 C1 C2 109.62(17) . . . yes
N1 C1 C5 113.73(17) . . . yes
C2 C1 C5 104.76(17) . . . no
C1 C2 C3 103.38(18) . . . no
C2 C3 C4 109.13(17) . . . no
C2 C3 C14 126.5(2) . . . no
C4 C3 C14 124.3(2) . . . no
C3 C4 C5 104.95(17) . . . no
C3 C4 C9 111.96(17) . . . no
C5 C4 C9 111.47(17) . . . no
C1 C5 C4 102.14(17) . . . no
C1 C5 C6 113.80(17) . . . no
C4 C5 C6 115.58(17) . . . no
C5 C6 C7 121.73(17) . . . no
C5 C6 C10 119.52(18) . . . no
C7 C6 C10 118.75(19) . . . no
C6 C7 C8 121.06(19) . . . no
C6 C7 C13 119.15(19) . . . no
C8 C7 C13 119.79(19) . . . no
C7 C8 C9 111.52(18) . . . no
C4 C9 C8 110.98(18) . . . no
C6 C10 C11 121.42(19) . . . no
C10 C11 C12 119.9(2) . . . no
C11 C12 C13 119.02(19) . . . no
C11 C12 C17 123.07(19) . . . no
C13 C12 C17 117.90(19) . . . no
C7 C13 C12 121.72(19) . . . no
C3 C14 C15 126.9(2) . . . no
C14 C15 C16 112.6(2) . . . no
O3 C17 O4 122.24(19) . . . yes
O3 C17 C12 124.62(19) . . . yes
O4 C17 C12 113.14(18) . . . yes
N1 C1 H1 110.00 . . . no
C2 C1 H1 110.00 . . . no
C5 C1 H1 110.00 . . . no
C1 C2 H2A 111.00 . . . no
C1 C2 H2B 111.00 . . . no
C3 C2 H2A 111.00 . . . no
C3 C2 H2B 111.00 . . . no
H2A C2 H2B 109.00 . . . no
C3 C4 H4 109.00 . . . no
C5 C4 H4 109.00 . . . no
C9 C4 H4 109.00 . . . no
C1 C5 H5 108.00 . . . no
C4 C5 H5 108.00 . . . no
C6 C5 H5 108.00 . . . no
C7 C8 H8A 109.00 . . . no
C7 C8 H8B 109.00 . . . no
C9 C8 H8A 109.00 . . . no
C9 C8 H8B 109.00 . . . no
H8A C8 H8B 108.00 . . . no
C4 C9 H9A 109.00 . . . no
C4 C9 H9B 109.00 . . . no
C8 C9 H9A 109.00 . . . no
C8 C9 H9B 109.00 . . . no
H9A C9 H9B 108.00 . . . no
C6 C10 H10 119.00 . . . no
C11 C10 H10 119.00 . . . no
C10 C11 H11 120.00 . . . no
C12 C11 H11 120.00 . . . no
C7 C13 H13 119.00 . . . no
C12 C13 H13 119.00 . . . no
C3 C14 H14 117.00 . . . no
C15 C14 H14 116.00 . . . no
C14 C15 H15A 109.00 . . . no
C14 C15 H15B 109.00 . . . no
C16 C15 H15A 109.00 . . . no
C16 C15 H15B 109.00 . . . no
H15A C15 H15B 108.00 . . . no
C15 C16 H16A 109.00 . . . no
C15 C16 H16B 109.00 . . . no
C15 C16 H16C 109.00 . . . no
H16A C16 H16B 109.00 . . . no
H16A C16 H16C 109.00 . . . no
H16B C16 H16C 110.00 . . . no
O4 C18 H18A 109.00 . . . no
O4 C18 H18B 110.00 . . . no
O4 C18 H18C 109.00 . . . no
H18A C18 H18B 109.00 . . . no
H18A C18 H18C 109.00 . . . no
H18B C18 H18C 109.00 . . . no

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
C18 O4 C17 O3 -1.7(3) . . . . no
C18 O4 C17 C12 178.03(18) . . . . no
O1 N1 C1 C2 -100.7(2) . . . . no
O1 N1 C1 C5 142.40(19) . . . . no
O2 N1 C1 C2 77.1(2) . . . . no
O2 N1 C1 C5 -39.8(3) . . . . no
N1 C1 C2 C3 -157.26(17) . . . . no
C5 C1 C2 C3 -34.9(2) . . . . no
N1 C1 C5 C4 159.54(17) . . . . no
N1 C1 C5 C6 -75.2(2) . . . . no
C2 C1 C5 C4 39.9(2) . . . . no
C2 C1 C5 C6 165.14(17) . . . . no
C1 C2 C3 C4 16.3(2) . . . . no
C1 C2 C3 C14 -162.7(2) . . . . no
C2 C3 C4 C5 8.2(2) . . . . no
C2 C3 C4 C9 -112.9(2) . . . . no
C14 C3 C4 C5 -172.8(2) . . . . no
C14 C3 C4 C9 66.2(3) . . . . no
C2 C3 C14 C15 -0.5(4) . . . . no
C4 C3 C14 C15 -179.4(2) . . . . no
C3 C4 C5 C1 -29.02(19) . . . . no
C3 C4 C5 C6 -153.12(17) . . . . no
C9 C4 C5 C1 92.4(2) . . . . no
C9 C4 C5 C6 -31.7(2) . . . . no
C3 C4 C9 C8 175.13(18) . . . . no
C5 C4 C9 C8 57.9(2) . . . . no
C1 C5 C6 C7 -113.4(2) . . . . no
C1 C5 C6 C10 66.0(2) . . . . no
C4 C5 C6 C7 4.4(3) . . . . no
C4 C5 C6 C10 -176.21(18) . . . . no
C5 C6 C7 C8 -2.4(3) . . . . no
C5 C6 C7 C13 176.81(19) . . . . no
C10 C6 C7 C8 178.1(2) . . . . no
C10 C6 C7 C13 -2.6(3) . . . . no
C5 C6 C10 C11 -176.5(2) . . . . no
C7 C6 C10 C11 2.9(3) . . . . no
C6 C7 C8 C9 28.1(3) . . . . no
C13 C7 C8 C9 -151.2(2) . . . . no
C6 C7 C13 C12 0.3(3) . . . . no
C8 C7 C13 C12 179.6(2) . . . . no
C7 C8 C9 C4 -55.7(3) . . . . no
C6 C10 C11 C12 -0.8(3) . . . . no
C10 C11 C12 C13 -1.6(3) . . . . no
C10 C11 C12 C17 179.8(2) . . . . no
C11 C12 C13 C7 1.8(3) . . . . no
C17 C12 C13 C7 -179.48(19) . . . . no
C11 C12 C17 O3 176.2(2) . . . . no
C11 C12 C17 O4 -3.5(3) . . . . no
C13 C12 C17 O3 -2.4(3) . . . . no
C13 C12 C17 O4 177.84(18) . . . . no
C3 C14 C15 C16 123.6(3) . . . . no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C2 H2A O1 0.9900 2.5400 3.486(3) 160.00 1_565 yes
C5 H5 O2 1.0000 2.5100 2.864(3) 100.00 . yes
C8 H8A O3 0.9900 2.5400 3.389(3) 144.00 3_666 yes
C8 H8B O3 0.9900 2.5400 3.475(3) 157.00 3_656 yes
C10 H10 O2 0.9500 2.5900 3.337(3) 136.00 . yes
C10 H10 O4 0.9500 2.5600 3.297(3) 134.00 2_656 yes
C18 H18B O2 0.9800 2.5100 3.247(3) 132.00 2_636 yes


