# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_exp_3361
_audit_block_doi                 10.5517/ccdc.csd.cc1m9s0q
_database_code_depnum_ccdc_archive 'CCDC 1498943'
_audit_update_record             
;
2016-08-12 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;
_audit_creation_date             2014-04-19
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H26 N O4'
_chemical_formula_sum            'C20 H26 N O4'
_chemical_formula_weight         344.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.1031(6)
_cell_length_b                   11.4651(12)
_cell_length_c                   26.396(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.114(9)
_cell_angle_gamma                90
_cell_volume                     1839.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1353
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      27.0500
_cell_measurement_theta_min      4.2210
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6912
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.012
_diffrn_reflns_theta_min         3.372
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9890
_diffrn_measured_fraction_theta_max 0.8328
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   81.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579   57.0000  -90.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega   35.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  178.0000  150.0000 66
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0102618000
_diffrn_orient_matrix_UB_12      -0.0616659000
_diffrn_orient_matrix_UB_13      -0.0002089000
_diffrn_orient_matrix_UB_21      0.0167371000
_diffrn_orient_matrix_UB_22      -0.0001388000
_diffrn_orient_matrix_UB_23      0.0269377000
_diffrn_orient_matrix_UB_31      -0.1149528000
_diffrn_orient_matrix_UB_32      -0.0054956000
_diffrn_orient_matrix_UB_33      0.0014415000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2307
_reflns_number_total             3597
_reflns_odcompleteness_completeness 98.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3597
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0707
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1169P)²+0.6908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1869
_refine_ls_wR_factor_ref         0.2242
_refine_special_details          
;
 ?
;
_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 Ternary CH refined with riding coordinates:
 C8(H8), N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.8853(5) 0.3171(3) 0.24893(10) 0.0317(7) Uani 1 1 d . . . . .
C2 C 1.0405(5) 0.3963(3) 0.27011(11) 0.0384(7) Uani 1 1 d . . . . .
H2 H 1.0200 0.4774 0.2638 0.046 Uiso 1 1 calc R U . . .
C3 C 1.2239(5) 0.3585(3) 0.30015(13) 0.0469(9) Uani 1 1 d . . . . .
H3 H 1.3278 0.4135 0.3145 0.056 Uiso 1 1 calc R U . . .
C4 C 1.2563(6) 0.2410(3) 0.30928(13) 0.0489(9) Uani 1 1 d . . . . .
H4 H 1.3822 0.2152 0.3300 0.059 Uiso 1 1 calc R U . . .
C5 C 1.1050(6) 0.1607(3) 0.28822(12) 0.0460(8) Uani 1 1 d . . . . .
H5 H 1.1272 0.0797 0.2942 0.055 Uiso 1 1 calc R U . . .
C6 C 0.9213(5) 0.1993(3) 0.25846(11) 0.0367(7) Uani 1 1 d . . . . .
H6 H 0.8175 0.1439 0.2442 0.044 Uiso 1 1 calc R U . . .
C7 C 0.6806(5) 0.3597(3) 0.21762(11) 0.0363(7) Uani 1 1 d . . . . .
H7A H 0.5612 0.3688 0.2404 0.044 Uiso 1 1 calc R U . . .
H7B H 0.7112 0.4376 0.2037 0.044 Uiso 1 1 calc R U . . .
C8 C 0.7414(4) 0.2569(2) 0.13087(10) 0.0277(6) Uani 1 1 d . . . . .
H8 H 0.8888 0.2283 0.1452 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6011(4) 0.2811(2) 0.17439(10) 0.0288(6) Uani 1 1 d . . . . .
C10 C 0.4054(4) 0.2308(3) 0.16651(11) 0.0329(7) Uani 1 1 d . . . . .
H10 H 0.2941 0.2379 0.1893 0.040 Uiso 1 1 calc R U . . .
C11 C 0.3769(4) 0.1618(3) 0.11833(11) 0.0326(7) Uani 1 1 d . . . . .
H11A H 0.2791 0.2025 0.0921 0.039 Uiso 1 1 calc R U . . .
H11B H 0.3163 0.0834 0.1243 0.039 Uiso 1 1 calc R U . . .
C12 C 0.6147(4) 0.1540(2) 0.10267(10) 0.0280(6) Uani 1 1 d . . . . .
C13 C 0.9684(5) 0.4265(3) 0.10930(15) 0.0478(9) Uani 1 1 d . . . . .
H13A H 1.1013 0.3853 0.0998 0.057 Uiso 1 1 calc R U . . .
H13B H 0.9880 0.4454 0.1460 0.057 Uiso 1 1 calc R U . . .
C14 C 0.9286(8) 0.5353(3) 0.07820(19) 0.0735(13) Uani 1 1 d . . . . .
H14A H 1.0364 0.5415 0.0524 0.088 Uiso 1 1 calc R U . . .
H14B H 0.9423 0.6052 0.1003 0.088 Uiso 1 1 calc R U . . .
C15 C 0.6989(7) 0.5255(3) 0.05280(16) 0.0577(10) Uani 1 1 d . . . . .
H15A H 0.7009 0.4992 0.0171 0.069 Uiso 1 1 calc R U . . .
H15B H 0.6213 0.6013 0.0532 0.069 Uiso 1 1 calc R U . . .
C16 C 0.5893(5) 0.4352(3) 0.08432(12) 0.0392(7) Uani 1 1 d . . . . .
H16A H 0.5344 0.4706 0.1150 0.047 Uiso 1 1 calc R U . . .
H16B H 0.4664 0.3957 0.0642 0.047 Uiso 1 1 calc R U . . .
C17 C 0.6345(5) 0.1641(3) 0.04589(11) 0.0337(7) Uani 1 1 d . . . . .
C18 C 0.8872(7) 0.1456(4) -0.01626(13) 0.0579(10) Uani 1 1 d . . . . .
H18A H 0.7864 0.0978 -0.0386 0.087 Uiso 1 1 calc R U . . .
H18B H 1.0390 0.1205 -0.0194 0.087 Uiso 1 1 calc R U . . .
H18C H 0.8709 0.2277 -0.0262 0.087 Uiso 1 1 calc R U . . .
C19 C 0.7131(5) 0.0384(2) 0.12087(10) 0.0303(7) Uani 1 1 d . . . . .
C20 C 0.6911(6) -0.1651(3) 0.10808(12) 0.0444(8) Uani 1 1 d . . . . .
H20A H 0.8510 -0.1674 0.1067 0.067 Uiso 1 1 calc R U . . .
H20B H 0.6213 -0.2216 0.0839 0.067 Uiso 1 1 calc R U . . .
H20C H 0.6554 -0.1847 0.1425 0.067 Uiso 1 1 calc R U . . .
N1 N 0.7723(4) 0.3551(2) 0.09764(9) 0.0307(6) Uani 1 1 d . . . . .
H1 H 0.7980 0.3176 0.0645 0.037 Uiso 1 1 calc R U . . .
O1 O 0.4933(4) 0.1984(2) 0.01461(8) 0.0450(6) Uani 1 1 d . . . . .
O2 O 0.8363(3) 0.13180(18) 0.03575(8) 0.0397(6) Uani 1 1 d . . . . .
O3 O 0.8590(4) 0.02473(18) 0.15385(9) 0.0458(6) Uani 1 1 d . . . . .
O4 O 0.6111(4) -0.04955(17) 0.09507(8) 0.0395(6) Uani 1 1 d . . . . .


_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 C2 1.393(4) . ?
C1 C6 1.388(4) . ?
C1 C7 1.516(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(4) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C9 1.500(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.518(4) . ?
C8 C12 1.563(4) . ?
C8 N1 1.449(4) . ?
C9 C10 1.326(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.495(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.546(4) . ?
C12 C17 1.519(4) . ?
C12 C19 1.515(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.501(5) . ?
C13 N1 1.461(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.504(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.520(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 N1 1.464(4) . ?
C17 O1 1.205(3) . ?
C17 O2 1.336(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 O2 1.443(4) . ?
C19 O3 1.199(3) . ?
C19 O4 1.339(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 O4 1.442(3) . ?
N1 H1 1.0000 . ?

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
C2 C1 C7 120.4(3) . . ?
C6 C1 C2 118.1(3) . . ?
C6 C1 C7 121.4(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 121.4(3) . . ?
C1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C1 C7 H7A 108.6 . . ?
C1 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C7 C1 114.6(2) . . ?
C9 C7 H7A 108.6 . . ?
C9 C7 H7B 108.6 . . ?
C9 C8 H8 108.8 . . ?
C9 C8 C12 102.1(2) . . ?
C12 C8 H8 108.8 . . ?
N1 C8 H8 108.8 . . ?
N1 C8 C9 115.4(2) . . ?
N1 C8 C12 112.6(2) . . ?
C7 C9 C8 121.3(2) . . ?
C10 C9 C7 127.3(2) . . ?
C10 C9 C8 111.3(2) . . ?
C9 C10 H10 123.3 . . ?
C9 C10 C11 113.5(2) . . ?
C11 C10 H10 123.3 . . ?
C10 C11 H11A 111.3 . . ?
C10 C11 H11B 111.3 . . ?
C10 C11 C12 102.6(2) . . ?
H11A C11 H11B 109.2 . . ?
C12 C11 H11A 111.3 . . ?
C12 C11 H11B 111.3 . . ?
C11 C12 C8 105.4(2) . . ?
C17 C12 C8 109.4(2) . . ?
C17 C12 C11 114.7(2) . . ?
C17 C12 C19 108.4(2) . . ?
C19 C12 C8 110.1(2) . . ?
C19 C12 C11 108.7(2) . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
N1 C13 H13A 110.7 . . ?
N1 C13 H13B 110.7 . . ?
N1 C13 C14 105.1(3) . . ?
C13 C14 H14A 110.5 . . ?
C13 C14 H14B 110.5 . . ?
C13 C14 C15 106.3(3) . . ?
H14A C14 H14B 108.7 . . ?
C15 C14 H14A 110.5 . . ?
C15 C14 H14B 110.5 . . ?
C14 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C14 C15 C16 104.2(3) . . ?
H15A C15 H15B 108.9 . . ?
C16 C15 H15A 110.9 . . ?
C16 C15 H15B 110.9 . . ?
C15 C16 H16A 111.5 . . ?
C15 C16 H16B 111.5 . . ?
H16A C16 H16B 109.3 . . ?
N1 C16 C15 101.3(3) . . ?
N1 C16 H16A 111.5 . . ?
N1 C16 H16B 111.5 . . ?
O1 C17 C12 125.9(3) . . ?
O1 C17 O2 124.7(3) . . ?
O2 C17 C12 109.4(2) . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
O3 C19 C12 126.3(3) . . ?
O3 C19 O4 123.5(3) . . ?
O4 C19 C12 110.1(2) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
C8 N1 C13 117.1(2) . . ?
C8 N1 C16 119.7(2) . . ?
C8 N1 H1 103.6 . . ?
C13 N1 C16 107.0(2) . . ?
C13 N1 H1 103.6 . . ?
C16 N1 H1 103.6 . . ?
C17 O2 C18 116.2(3) . . ?
C19 O4 C20 116.0(2) . . ?

_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.983
_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.
;
_shelxl_version_number           2013-3
