# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_gui87_R_11a
_database_code_depnum_ccdc_archive 'CCDC 1565411'
_audit_update_record             
;
2017-07-28 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N O4'
_chemical_formula_sum            'C21 H23 N O4'
_chemical_formula_weight         353.40
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.75356(7)
_cell_length_b                   8.85744(5)
_cell_length_c                   24.7460(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1918.66(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12137
_cell_measurement_theta_min      5.3470
_cell_measurement_theta_max      76.6030

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3749
_exptl_crystal_size_mid          0.1296
_exptl_crystal_size_min          0.0915
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;

_exptl_special_details           
; 
 1678 Friedel pairs were measured. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19851
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         76.90
_reflns_number_total             3983
_reflns_number_gt                3802
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0415P)²+0.2036P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_number_reflns         3983
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_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 1.08310(14) 0.98406(13) 0.85967(4) 0.0200(2) Uani 1 1 d . . .
N N 1.14425(12) 0.85692(11) 0.88272(4) 0.0222(2) Uani 1 1 d . . .
C9 C 1.30099(16) 0.80882(15) 0.87514(6) 0.0326(3) Uani 1 1 d . . .
H9A H 1.3535 0.8801 0.8512 0.049 Uiso 1 1 calc R . .
H9B H 1.3024 0.7079 0.8589 0.049 Uiso 1 1 calc R . .
H9C H 1.3530 0.8059 0.9102 0.049 Uiso 1 1 calc R . .
O1 O 1.15461(10) 1.07737(9) 0.83375(3) 0.02483(18) Uani 1 1 d . . .
C2 C 0.91404(13) 0.99667(12) 0.87822(4) 0.0194(2) Uani 1 1 d . . .
C10 C 0.91407(14) 1.14008(14) 0.91520(4) 0.0232(2) Uani 1 1 d . . .
H10A H 0.9394 1.2296 0.8930 0.028 Uiso 1 1 calc R . .
H10B H 0.8101 1.1550 0.9300 0.028 Uiso 1 1 calc R . .
C11 C 1.02532(15) 1.12969(13) 0.96107(5) 0.0256(2) Uani 1 1 d . . .
H11 H 1.0079 1.0542 0.9876 0.031 Uiso 1 1 calc R . .
C12 C 1.14549(16) 1.21757(16) 0.96731(5) 0.0324(3) Uani 1 1 d . . .
H12A H 1.1666 1.2944 0.9416 0.039 Uiso 1 1 calc R . .
H12B H 1.2110 1.2041 0.9975 0.039 Uiso 1 1 calc R . .
C3 C 0.89510(14) 0.85270(13) 0.91043(4) 0.0211(2) Uani 1 1 d . . .
C4 C 0.76997(16) 0.79463(15) 0.93728(5) 0.0272(3) Uani 1 1 d . . .
H4 H 0.6751 0.8467 0.9371 0.033 Uiso 1 1 calc R . .
C5 C 0.78566(18) 0.65746(16) 0.96484(6) 0.0349(3) Uani 1 1 d . . .
H5 H 0.7008 0.6161 0.9836 0.042 Uiso 1 1 calc R . .
C6 C 0.92416(18) 0.58162(15) 0.96494(6) 0.0368(3) Uani 1 1 d . . .
H6 H 0.9326 0.4886 0.9838 0.044 Uiso 1 1 calc R . .
C7 C 1.05111(17) 0.63876(15) 0.93798(5) 0.0311(3) Uani 1 1 d . . .
H7 H 1.1458 0.5864 0.9380 0.037 Uiso 1 1 calc R . .
C8 C 1.03390(15) 0.77514(13) 0.91117(5) 0.0229(2) Uani 1 1 d . . .
C13 C 0.80178(13) 1.00675(12) 0.83081(4) 0.0194(2) Uani 1 1 d . . .
C14 C 0.65686(14) 1.07345(13) 0.83385(4) 0.0209(2) Uani 1 1 d . . .
O2 O 0.60863(10) 1.11888(10) 0.88396(3) 0.02728(19) Uani 1 1 d . . .
C19 C 0.48094(15) 1.21865(15) 0.88744(5) 0.0278(3) Uani 1 1 d . . .
H19A H 0.4991 1.3071 0.8646 0.042 Uiso 1 1 calc R . .
H19B H 0.4674 1.2511 0.9250 0.042 Uiso 1 1 calc R . .
H19C H 0.3887 1.1662 0.8752 0.042 Uiso 1 1 calc R . .
C15 C 0.56173(14) 1.08831(13) 0.78883(5) 0.0223(2) Uani 1 1 d . . .
H15 H 0.4660 1.1382 0.7917 0.027 Uiso 1 1 calc R . .
C16 C 0.60990(14) 1.02863(12) 0.73973(4) 0.0212(2) Uani 1 1 d . . .
O3 O 0.52395(10) 1.03374(9) 0.69350(3) 0.02530(19) Uani 1 1 d . . .
C20 C 0.38564(15) 1.11962(15) 0.69486(5) 0.0308(3) Uani 1 1 d . . .
H20A H 0.3184 1.0797 0.7231 0.046 Uiso 1 1 calc R . .
H20B H 0.3343 1.1125 0.6598 0.046 Uiso 1 1 calc R . .
H20C H 0.4095 1.2255 0.7026 0.046 Uiso 1 1 calc R . .
C17 C 0.74768(14) 0.95232(13) 0.73540(4) 0.0223(2) Uani 1 1 d . . .
H17 H 0.7787 0.9096 0.7019 0.027 Uiso 1 1 calc R . .
C18 C 0.83965(14) 0.93952(12) 0.78101(4) 0.0208(2) Uani 1 1 d . . .
O4 O 0.97001(10) 0.85541(10) 0.78113(3) 0.02698(19) Uani 1 1 d . . .
C21 C 1.05098(16) 0.84049(16) 0.73124(5) 0.0302(3) Uani 1 1 d . . .
H21A H 0.9958 0.7709 0.7074 0.045 Uiso 1 1 calc R . .
H21B H 1.1536 0.8009 0.7383 0.045 Uiso 1 1 calc R . .
H21C H 1.0590 0.9395 0.7138 0.045 Uiso 1 1 calc R . .


_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 O1 1.2191(15) . ?
C1 N 1.3712(15) . ?
C1 C2 1.5535(17) . ?
N C8 1.3976(16) . ?
N C9 1.4489(16) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C2 C3 1.5129(15) . ?
C2 C13 1.5330(15) . ?
C2 C10 1.5656(15) . ?
C10 C11 1.4984(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.3176(19) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9500 . ?
C12 H12B 0.9500 . ?
C3 C4 1.3805(18) . ?
C3 C8 1.3959(17) . ?
C4 C5 1.4001(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3864(17) . ?
C7 H7 0.9500 . ?
C13 C14 1.4015(16) . ?
C13 C18 1.4082(15) . ?
C14 O2 1.3703(13) . ?
C14 C15 1.3970(16) . ?
O2 C19 1.4275(14) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C15 C16 1.3905(15) . ?
C15 H15 0.9500 . ?
C16 O3 1.3700(13) . ?
C16 C17 1.3867(17) . ?
O3 C20 1.4302(15) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C17 C18 1.3909(16) . ?
C17 H17 0.9500 . ?
C18 O4 1.3628(15) . ?
O4 C21 1.4296(14) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
O1 C1 N 125.12(11) . . ?
O1 C1 C2 126.57(10) . . ?
N C1 C2 107.94(10) . . ?
C1 N C8 111.44(10) . . ?
C1 N C9 123.87(11) . . ?
C8 N C9 124.56(10) . . ?
N C9 H9A 109.5 . . ?
N C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C2 C13 112.46(9) . . ?
C3 C2 C1 101.50(9) . . ?
C13 C2 C1 112.87(9) . . ?
C3 C2 C10 112.08(9) . . ?
C13 C2 C10 113.60(9) . . ?
C1 C2 C10 103.35(9) . . ?
C11 C10 C2 113.15(9) . . ?
C11 C10 H10A 108.9 . . ?
C2 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C2 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 124.84(12) . . ?
C12 C11 H11 117.6 . . ?
C10 C11 H11 117.6 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C4 C3 C8 120.06(11) . . ?
C4 C3 C2 130.88(11) . . ?
C8 C3 C2 109.05(10) . . ?
C3 C4 C5 118.68(12) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 120.48(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.43(12) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 117.36(13) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C7 C8 C3 121.98(12) . . ?
C7 C8 N 128.14(12) . . ?
C3 C8 N 109.87(10) . . ?
C14 C13 C18 116.00(10) . . ?
C14 C13 C2 124.31(9) . . ?
C18 C13 C2 119.62(10) . . ?
O2 C14 C15 120.68(10) . . ?
O2 C14 C13 116.82(10) . . ?
C15 C14 C13 122.44(10) . . ?
C14 O2 C19 118.54(9) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C15 C14 118.69(11) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
O3 C16 C17 115.42(10) . . ?
O3 C16 C15 123.40(11) . . ?
C17 C16 C15 121.10(10) . . ?
C16 O3 C20 117.57(9) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C17 C18 118.72(10) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
O4 C18 C17 122.08(10) . . ?
O4 C18 C13 115.23(10) . . ?
C17 C18 C13 122.63(11) . . ?
C18 O4 C21 117.63(9) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
O1 C1 N C8 178.13(11) . . . . ?
C2 C1 N C8 4.78(12) . . . . ?
O1 C1 N C9 -5.92(18) . . . . ?
C2 C1 N C9 -179.27(11) . . . . ?
O1 C1 C2 C3 -177.16(11) . . . . ?
N C1 C2 C3 -3.93(11) . . . . ?
O1 C1 C2 C13 62.25(14) . . . . ?
N C1 C2 C13 -124.52(10) . . . . ?
O1 C1 C2 C10 -60.89(14) . . . . ?
N C1 C2 C10 112.34(10) . . . . ?
C3 C2 C10 C11 51.76(14) . . . . ?
C13 C2 C10 C11 -179.40(10) . . . . ?
C1 C2 C10 C11 -56.75(12) . . . . ?
C2 C10 C11 C12 115.37(13) . . . . ?
C13 C2 C3 C4 -58.17(16) . . . . ?
C1 C2 C3 C4 -179.05(12) . . . . ?
C10 C2 C3 C4 71.26(16) . . . . ?
C13 C2 C3 C8 122.70(10) . . . . ?
C1 C2 C3 C8 1.82(11) . . . . ?
C10 C2 C3 C8 -107.87(11) . . . . ?
C8 C3 C4 C5 -0.13(18) . . . . ?
C2 C3 C4 C5 -179.18(11) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
C6 C7 C8 C3 -0.61(19) . . . . ?
C6 C7 C8 N 178.10(12) . . . . ?
C4 C3 C8 C7 0.54(18) . . . . ?
C2 C3 C8 C7 179.77(11) . . . . ?
C4 C3 C8 N -178.38(10) . . . . ?
C2 C3 C8 N 0.85(13) . . . . ?
C1 N C8 C7 177.51(12) . . . . ?
C9 N C8 C7 1.6(2) . . . . ?
C1 N C8 C3 -3.66(13) . . . . ?
C9 N C8 C3 -179.57(11) . . . . ?
C3 C2 C13 C14 90.94(13) . . . . ?
C1 C2 C13 C14 -154.94(10) . . . . ?
C10 C2 C13 C14 -37.70(15) . . . . ?
C3 C2 C13 C18 -85.83(12) . . . . ?
C1 C2 C13 C18 28.28(14) . . . . ?
C10 C2 C13 C18 145.53(11) . . . . ?
C18 C13 C14 O2 170.36(10) . . . . ?
C2 C13 C14 O2 -6.52(16) . . . . ?
C18 C13 C14 C15 -7.06(16) . . . . ?
C2 C13 C14 C15 176.07(11) . . . . ?
C15 C14 O2 C19 -17.49(16) . . . . ?
C13 C14 O2 C19 165.05(10) . . . . ?
O2 C14 C15 C16 -174.37(10) . . . . ?
C13 C14 C15 C16 2.95(17) . . . . ?
C14 C15 C16 O3 178.34(10) . . . . ?
C14 C15 C16 C17 1.61(17) . . . . ?
C17 C16 O3 C20 -175.95(10) . . . . ?
C15 C16 O3 C20 7.15(16) . . . . ?
O3 C16 C17 C18 -178.59(10) . . . . ?
C15 C16 C17 C18 -1.61(17) . . . . ?
C16 C17 C18 O4 174.26(10) . . . . ?
C16 C17 C18 C13 -2.94(17) . . . . ?
C14 C13 C18 O4 -170.31(10) . . . . ?
C2 C13 C18 O4 6.72(15) . . . . ?
C14 C13 C18 C17 7.07(17) . . . . ?
C2 C13 C18 C17 -175.89(10) . . . . ?
C17 C18 O4 C21 29.65(16) . . . . ?
C13 C18 O4 C21 -152.95(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        76.90
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
