# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
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data_RC438
_database_code_depnum_ccdc_archive 'CCDC 1526432'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;
_audit_creation_date             2014-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H29 N O5'
_chemical_formula_sum            'C21 H29 N O5'
_chemical_formula_weight         375.45
_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 0.0033 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'

_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                   19.8561(10)
_cell_length_b                   7.9076(4)
_cell_length_c                   12.5788(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.5550(16)
_cell_angle_gamma                90
_cell_volume                     1935.02(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4281
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.88
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0670 before and 0.0640 after correction.
The Ratio of minimum to maximum transmission is 0.9455.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18865
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.055
_diffrn_reflns_theta_min         2.781
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2584
_reflns_number_total             3815
_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       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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, 2008)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3815
_refine_ls_number_restraints     231
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      0.992
_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)+(0.0406P)²+0.8067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1058
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H27(0.031) H3(0.041) H4(0.039) H6(0.034) H7(0.03) H8(0.023)
 H9A(0.025) H9B(0.025) H10(0.023) H12(0.02) H16A(0.046) H16B(0.046) H16C(0.046)
 H18A(0.066) H18B(0.066) H18C(0.066) H20A(0.027) H20B(0.027) H21A(0.024)
 H21B(0.024) H22A(0.044) H22B(0.044) H22C(0.044) H24A(0.047) H24B(0.047)
 H24C(0.047) H26A(0.052) H26B(0.052) H26C(0.052)
 Fixed X: H27(0.8165) H3(0.503) H4(0.5631) H6(0.655) H7(0.7647) H8(0.8067)
 H9A(0.8328) H9B(0.8853) H10(0.9238) H12(0.774) H16A(0.6771) H16B(0.7166)
 H16C(0.6352) H18A(0.467) H18B(0.4507) H18C(0.4437) H20A(0.7762) H20B(0.7521)
 H21A(0.6782) H21B(0.7173) H22A(0.9317) H22B(0.8662) H22C(0.8845) H24A(0.9184)
 H24B(0.9208) H24C(0.8484) H26A(1.0006) H26B(0.9865) H26C(0.9956)
 Fixed Y: H27(0.8093) H3(0.6656) H4(0.4423) H6(0.3341) H7(0.3531) H8(0.5862)
 H9A(0.5704) H9B(0.5439) H10(0.788) H12(1.013) H16A(1.0435) H16B(1.1903)
 H16C(1.2019) H18A(0.8977) H18B(1.0821) H18C(0.9198) H20A(1.0507) H20B(0.9758)
 H21A(0.8833) H21B(0.7252) H22A(0.9672) H22B(1.038) H22C(1.1104) H24A(1.1012)
 H24B(1.2643) H24C(1.1865) H26A(0.7625) H26B(0.6891) H26C(0.8883)
 Fixed Z: H27(0.4723) H3(0.374) H4(0.4681) H6(0.6114) H7(0.7046) H8(0.5872)
 H9A(0.8156) H9B(0.7358) H10(0.8049) H12(0.6104) H16A(0.3608) H16B(0.436)
 H16C(0.393) H18A(0.2706) H18B(0.3115) H18C(0.3845) H20A(0.7745) H20B(0.8787)
 H21A(0.7238) H21B(0.7866) H22A(0.9401) H22B(0.9823) H22C(0.8727) H24A(0.5447)
 H24B(0.6207) H24C(0.5624) H26A(0.5757) H26B(0.6878) H26C(0.6735)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O15 O 0.66295(6) 1.03583(16) 0.51359(10) 0.0241(3) Uani 1 1 d . . . . .
O17 O 0.54032(7) 0.9886(2) 0.38763(11) 0.0371(4) Uani 1 1 d . . . . .
O23 O 0.89617(6) 1.05263(16) 0.68844(10) 0.0228(3) Uani 1 1 d . . . . .
O25 O 0.90546(6) 0.80009(17) 0.59691(10) 0.0229(3) Uani 1 1 d . . . . .
O27 O 0.78996(6) 0.88658(17) 0.48415(9) 0.0204(3) Uani 1 1 d . . . . .
H27 H 0.8165 0.8093 0.4723 0.031 Uiso 1 1 calc GR . . . .
N19 N 0.84170(8) 0.8788(2) 0.85559(12) 0.0209(4) Uani 1 1 d . . . . .
C1 C 0.63910(9) 0.8722(3) 0.49716(15) 0.0220(4) Uani 1 1 d . . . . .
C2 C 0.57351(10) 0.8453(3) 0.43220(16) 0.0283(5) Uani 1 1 d . . . . .
C3 C 0.54630(10) 0.6850(3) 0.42031(17) 0.0338(5) Uani 1 1 d . . . . .
H3 H 0.5030 0.6656 0.3740 0.041 Uiso 1 1 calc R . . . .
C4 C 0.58233(10) 0.5527(3) 0.47608(16) 0.0323(5) Uani 1 1 d . . . . .
H4 H 0.5631 0.4423 0.4681 0.039 Uiso 1 1 calc R . . . .
C5 C 0.64628(10) 0.5770(2) 0.54389(15) 0.0246(4) Uani 1 1 d . . . . .
C6 C 0.67999(11) 0.4356(2) 0.60782(16) 0.0283(5) Uani 1 1 d . . . . .
H6 H 0.6550 0.3341 0.6114 0.034 Uiso 1 1 calc R . . . .
C7 C 0.74468(10) 0.4454(2) 0.66109(15) 0.0252(5) Uani 1 1 d . . . . .
H7 H 0.7647 0.3531 0.7046 0.030 Uiso 1 1 calc R . . . .
C8 C 0.78632(9) 0.6009(2) 0.65309(14) 0.0192(4) Uani 1 1 d . . . . .
H8 H 0.8067 0.5862 0.5872 0.023 Uiso 1 1 calc R . . . .
C9 C 0.84713(9) 0.6153(2) 0.75003(14) 0.0210(4) Uani 1 1 d . . . . .
H9A H 0.8328 0.5704 0.8156 0.025 Uiso 1 1 calc R . . . .
H9B H 0.8853 0.5439 0.7358 0.025 Uiso 1 1 calc R . . . .
C10 C 0.87358(9) 0.7970(2) 0.77310(14) 0.0193(4) Uani 1 1 d . . . . .
H10 H 0.9238 0.7880 0.8049 0.023 Uiso 1 1 calc R . . . .
C11 C 0.86747(9) 0.8893(2) 0.66383(14) 0.0182(4) Uani 1 1 d . . . . .
C12 C 0.79222(9) 0.8987(2) 0.59694(13) 0.0167(4) Uani 1 1 d . . . . .
H12 H 0.7740 1.0130 0.6104 0.020 Uiso 1 1 calc R . . . .
C13 C 0.74446(9) 0.7661(2) 0.63619(14) 0.0178(4) Uani 1 1 d . . . . .
C14 C 0.67655(9) 0.7393(2) 0.55328(14) 0.0200(4) Uani 1 1 d . . . . .
C16 C 0.67381(11) 1.1251(3) 0.41817(16) 0.0307(5) Uani 1 1 d . . . . .
H16A H 0.6771 1.0435 0.3608 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.7166 1.1903 0.4360 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.6352 1.2019 0.3930 0.046 Uiso 1 1 calc GR . . . .
C18 C 0.46987(10) 0.9706(4) 0.33436(18) 0.0442(6) Uani 1 1 d . . . . .
H18A H 0.4670 0.8977 0.2706 0.066 Uiso 1 1 calc GR . . . .
H18B H 0.4507 1.0821 0.3115 0.066 Uiso 1 1 calc GR . . . .
H18C H 0.4437 0.9198 0.3845 0.066 Uiso 1 1 calc GR . . . .
C20 C 0.77236(10) 0.9454(2) 0.81549(15) 0.0224(4) Uani 1 1 d . . . . .
H20A H 0.7762 1.0507 0.7745 0.027 Uiso 1 1 calc R . . . .
H20B H 0.7521 0.9758 0.8787 0.027 Uiso 1 1 calc R . . . .
C21 C 0.72350(9) 0.8266(2) 0.74337(14) 0.0202(4) Uani 1 1 d . . . . .
H21A H 0.6782 0.8833 0.7238 0.024 Uiso 1 1 calc R . . . .
H21B H 0.7173 0.7252 0.7866 0.024 Uiso 1 1 calc R . . . .
C22 C 0.88454(10) 1.0093(3) 0.91779(15) 0.0294(5) Uani 1 1 d . . . . .
H22A H 0.9317 0.9672 0.9401 0.044 Uiso 1 1 calc GR . . . .
H22B H 0.8662 1.0380 0.9823 0.044 Uiso 1 1 calc GR . . . .
H22C H 0.8845 1.1104 0.8727 0.044 Uiso 1 1 calc GR . . . .
C24 C 0.89592(11) 1.1595(3) 0.59688(16) 0.0314(5) Uani 1 1 d . . . . .
H24A H 0.9184 1.1012 0.5447 0.047 Uiso 1 1 calc GR . . . .
H24B H 0.9208 1.2643 0.6207 0.047 Uiso 1 1 calc GR . . . .
H24C H 0.8484 1.1865 0.5624 0.047 Uiso 1 1 calc GR . . . .
C26 C 0.97767(9) 0.7837(3) 0.63658(17) 0.0344(5) Uani 1 1 d . . . . .
H26A H 1.0006 0.7625 0.5757 0.052 Uiso 1 1 calc GR . . . .
H26B H 0.9865 0.6891 0.6878 0.052 Uiso 1 1 calc GR . . . .
H26C H 0.9956 0.8883 0.6735 0.052 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
O15 C1 1.379(2) . ?
O15 C16 1.445(2) . ?
O17 C2 1.373(2) . ?
O17 C18 1.432(2) . ?
O23 C11 1.421(2) . ?
O23 C24 1.428(2) . ?
O25 C11 1.425(2) . ?
O25 C26 1.427(2) . ?
O27 C12 1.414(2) . ?
N19 C10 1.469(2) . ?
N19 C20 1.466(2) . ?
N19 C22 1.461(2) . ?
C1 C2 1.408(3) . ?
C1 C14 1.395(3) . ?
C2 C3 1.374(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.459(3) . ?
C5 C14 1.412(3) . ?
C6 C7 1.327(3) . ?
C7 C8 1.496(3) . ?
C8 C9 1.539(2) . ?
C8 C13 1.540(3) . ?
C9 C10 1.537(3) . ?
C10 C11 1.539(2) . ?
C11 C12 1.563(2) . ?
C12 C13 1.559(2) . ?
C13 C14 1.545(2) . ?
C13 C21 1.564(2) . ?
C20 C21 1.515(3) . ?

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 O15 C16 115.94(15) . . ?
C2 O17 C18 116.93(18) . . ?
C11 O23 C24 115.22(14) . . ?
C11 O25 C26 116.89(14) . . ?
C20 N19 C10 115.02(13) . . ?
C22 N19 C10 113.72(14) . . ?
C22 N19 C20 109.64(15) . . ?
O15 C1 C2 118.61(17) . . ?
O15 C1 C14 119.93(16) . . ?
C14 C1 C2 121.13(18) . . ?
O17 C2 C1 115.12(18) . . ?
O17 C2 C3 124.81(18) . . ?
C3 C2 C1 120.03(19) . . ?
C2 C3 C4 119.50(19) . . ?
C3 C4 C5 121.6(2) . . ?
C4 C5 C6 119.54(18) . . ?
C4 C5 C14 119.78(19) . . ?
C14 C5 C6 120.64(17) . . ?
C7 C6 C5 121.66(18) . . ?
C6 C7 C8 120.39(18) . . ?
C7 C8 C9 111.35(15) . . ?
C7 C8 C13 114.59(15) . . ?
C9 C8 C13 111.25(15) . . ?
C10 C9 C8 113.77(15) . . ?
N19 C10 C9 111.44(14) . . ?
N19 C10 C11 116.99(15) . . ?
C9 C10 C11 108.17(14) . . ?
O23 C11 O25 110.01(13) . . ?
O23 C11 C10 106.27(14) . . ?
O23 C11 C12 111.86(15) . . ?
O25 C11 C10 109.67(15) . . ?
O25 C11 C12 105.53(13) . . ?
C10 C11 C12 113.52(14) . . ?
O27 C12 C11 111.83(13) . . ?
O27 C12 C13 111.90(14) . . ?
C13 C12 C11 111.96(14) . . ?
C8 C13 C12 105.59(14) . . ?
C8 C13 C14 110.53(15) . . ?
C8 C13 C21 111.74(15) . . ?
C12 C13 C21 110.53(14) . . ?
C14 C13 C12 112.48(14) . . ?
C14 C13 C21 106.08(13) . . ?
C1 C14 C5 117.89(17) . . ?
C1 C14 C13 122.88(16) . . ?
C5 C14 C13 118.71(17) . . ?
N19 C20 C21 115.33(15) . . ?
C20 C21 C13 117.21(14) . . ?
