# 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. 
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#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1491982'
_audit_update_record             
;
2016-07-11 deposited with the CCDC.
2016-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H25 N3 O4'
_chemical_formula_weight         419.47

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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.
;

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

_cell_length_a                   22.3944(3)
_cell_length_b                   10.7588(2)
_cell_length_c                   19.4913(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.440(2)
_cell_angle_gamma                90
_cell_volume                     4526.69(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    9684
_cell_measurement_theta_min      4.5790
_cell_measurement_theta_max      71.1530

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             1776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.691
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_T_min  0.78427
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_reflns_number            19485
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.096
_diffrn_reflns_theta_max         71.264
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4333
_reflns_number_gt                3685
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0958P)²+5.1586P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4333
_refine_ls_number_parameters     281
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.2049
_refine_ls_wR_factor_gt          0.1977
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.208
_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_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
O3 O 0.43825(7) 0.72925(17) 0.48258(8) 0.0565(4) Uani 1 1 d . . . . .
O2 O 0.51992(9) 0.86101(19) 0.42307(10) 0.0701(5) Uani 1 1 d . . . . .
N1 N 0.58909(9) 0.81700(19) 0.59580(10) 0.0544(5) Uani 1 1 d . . . . .
O4 O 0.44445(10) 0.5912(2) 0.39791(10) 0.0761(6) Uani 1 1 d . . . . .
N3 N 0.62575(11) 0.7262(3) 0.40298(13) 0.0737(7) Uani 1 1 d . . . . .
N2 N 0.60665(11) 0.5836(2) 0.47671(14) 0.0724(6) Uani 1 1 d . . . . .
O1 O 0.71334(11) 0.8519(3) 0.67489(15) 0.1114(9) Uani 1 1 d . . . . .
C12 C 0.49028(11) 0.7743(2) 0.63267(11) 0.0522(5) Uani 1 1 d . . . . .
C8 C 0.58939(11) 0.6922(3) 0.44579(13) 0.0577(6) Uani 1 1 d . . . . .
C7 C 0.53765(11) 0.7658(2) 0.45586(11) 0.0534(5) Uani 1 1 d . . . . .
C6 C 0.50504(10) 0.7186(2) 0.51077(11) 0.0521(5) Uani 1 1 d . . . . .
H6 H 0.5174 0.6332 0.5255 0.062 Uiso 1 1 calc R U . . .
C5 C 0.52078(11) 0.8074(2) 0.57372(11) 0.0524(5) Uani 1 1 d . . . . .
H5 H 0.5049 0.8892 0.5556 0.063 Uiso 1 1 calc R U . . .
C13 C 0.47510(12) 0.6543(2) 0.64625(13) 0.0604(6) Uani 1 1 d . . . . .
H13 H 0.4804 0.5902 0.6163 0.072 Uiso 1 1 calc R U . . .
C18 C 0.41404(12) 0.6565(3) 0.42509(13) 0.0612(6) Uani 1 1 d . . . . .
C14 C 0.45201(12) 0.6279(3) 0.70411(14) 0.0649(7) Uani 1 1 d . . . . .
H14 H 0.4416 0.5467 0.7124 0.078 Uiso 1 1 calc R U . . .
C17 C 0.48035(13) 0.8682(3) 0.67676(13) 0.0655(7) Uani 1 1 d . . . . .
H17 H 0.4884 0.9503 0.6671 0.079 Uiso 1 1 calc R U . . .
C15 C 0.44458(13) 0.7210(3) 0.74885(13) 0.0684(7) Uani 1 1 d . . . . .
H15 H 0.4302 0.7030 0.7883 0.082 Uiso 1 1 calc R U . . .
C16 C 0.45851(15) 0.8412(3) 0.73523(15) 0.0756(8) Uani 1 1 d . . . . .
H16 H 0.4533 0.9049 0.7654 0.091 Uiso 1 1 calc R U . . .
C2 C 0.62181(12) 0.7215(3) 0.64366(16) 0.0706(7) Uani 1 1 d . . . . .
H2A H 0.6075 0.6401 0.6249 0.085 Uiso 1 1 calc R U . . .
H2B H 0.6136 0.7304 0.6898 0.085 Uiso 1 1 calc R U . . .
C19 C 0.34603(14) 0.6726(3) 0.39915(16) 0.0808(10) Uani 1 1 d . . . . .
C3 C 0.61235(15) 0.9393(3) 0.6218(2) 0.0849(9) Uani 1 1 d . . . . .
H3A H 0.6046 0.9548 0.6677 0.102 Uiso 1 1 calc R U . . .
H3B H 0.5913 1.0029 0.5889 0.102 Uiso 1 1 calc R U . . .
C1 C 0.69005(14) 0.7328(4) 0.6515(2) 0.0945(11) Uani 1 1 d . . . . .
H1A H 0.7118 0.6710 0.6853 0.113 Uiso 1 1 calc R U . . .
H1B H 0.6982 0.7154 0.6060 0.113 Uiso 1 1 calc R U . . .
C9 C 0.66758(15) 0.6320(4) 0.4088(2) 0.0956(11) Uani 1 1 d . . . . .
H9 H 0.6988 0.6274 0.3856 0.115 Uiso 1 1 calc R U . . .
C10 C 0.65579(15) 0.5474(4) 0.4539(2) 0.0937(11) Uani 1 1 d . . . . .
H10 H 0.6781 0.4744 0.4674 0.112 Uiso 1 1 calc R U . . .
C11 C 0.62245(19) 0.8391(4) 0.3600(2) 0.1105(14) Uani 1 1 d . . . . .
H11A H 0.5838 0.8408 0.3239 0.166 Uiso 1 1 calc R U . . .
H11B H 0.6560 0.8395 0.3380 0.166 Uiso 1 1 calc R U . . .
H11C H 0.6254 0.9108 0.3900 0.166 Uiso 1 1 calc R U . . .
C24 C 0.31415(17) 0.7457(5) 0.4333(2) 0.1059(12) Uani 1 1 d . U . . .
H24 H 0.3353 0.7877 0.4743 0.127 Uiso 1 1 calc R U . . .
C22 C 0.2220(2) 0.6920(6) 0.3476(3) 0.1362(16) Uani 1 1 d . U . . .
H22 H 0.1792 0.6997 0.3299 0.163 Uiso 1 1 calc R U . . .
C4 C 0.68042(18) 0.9434(4) 0.6287(3) 0.1196(15) Uani 1 1 d . . . . .
H4A H 0.6874 0.9323 0.5821 0.144 Uiso 1 1 calc R U . . .
H4B H 0.6962 1.0247 0.6462 0.144 Uiso 1 1 calc R U . . .
C20 C 0.3149(2) 0.6086(4) 0.3380(2) 0.1180(14) Uani 1 1 d . U . . .
H20 H 0.3369 0.5595 0.3138 0.142 Uiso 1 1 calc R U . . .
C23 C 0.2502(2) 0.7592(5) 0.4083(3) 0.1306(14) Uani 1 1 d . U . . .
H23 H 0.2278 0.8102 0.4309 0.157 Uiso 1 1 calc R U . . .
C21 C 0.2506(3) 0.6186(6) 0.3131(3) 0.1504(19) Uani 1 1 d . U . . .
H21 H 0.2288 0.5745 0.2733 0.180 Uiso 1 1 calc R U . . .


_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
O3 C18 1.356(3) . ?
O3 C6 1.454(3) . ?
O2 C7 1.217(3) . ?
N1 C2 1.449(3) . ?
N1 C3 1.456(4) . ?
N1 C5 1.478(3) . ?
O4 C18 1.196(3) . ?
N3 C8 1.362(3) . ?
N3 C9 1.364(4) . ?
N3 C11 1.465(5) . ?
N2 C8 1.324(4) . ?
N2 C10 1.350(4) . ?
O1 C4 1.403(5) . ?
O1 C1 1.413(5) . ?
C12 C13 1.379(4) . ?
C12 C17 1.382(3) . ?
C12 C5 1.527(3) . ?
C8 C7 1.459(3) . ?
C7 C6 1.534(3) . ?
C6 C5 1.521(3) . ?
C6 H6 0.9800 . ?
C5 H5 0.9800 . ?
C13 C14 1.389(4) . ?
C13 H13 0.9300 . ?
C18 C19 1.482(4) . ?
C14 C15 1.367(4) . ?
C14 H14 0.9300 . ?
C17 C16 1.385(4) . ?
C17 H17 0.9300 . ?
C15 C16 1.373(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C2 C1 1.500(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C19 C24 1.351(6) . ?
C19 C20 1.393(5) . ?
C3 C4 1.495(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C9 C10 1.340(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C24 C23 1.392(5) . ?
C24 H24 0.9300 . ?
C22 C21 1.310(8) . ?
C22 C23 1.387(8) . ?
C22 H22 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C20 C21 1.396(7) . ?
C20 H20 0.9300 . ?
C23 H23 0.9300 . ?
C21 H21 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
C18 O3 C6 114.29(19) . . ?
C2 N1 C3 110.1(2) . . ?
C2 N1 C5 116.4(2) . . ?
C3 N1 C5 114.3(2) . . ?
C8 N3 C9 105.0(3) . . ?
C8 N3 C11 128.7(3) . . ?
C9 N3 C11 126.3(3) . . ?
C8 N2 C10 105.6(3) . . ?
C4 O1 C1 110.1(3) . . ?
C13 C12 C17 118.5(2) . . ?
C13 C12 C5 123.0(2) . . ?
C17 C12 C5 118.4(2) . . ?
N2 C8 N3 111.5(2) . . ?
N2 C8 C7 124.3(2) . . ?
N3 C8 C7 124.2(3) . . ?
O2 C7 C8 123.1(2) . . ?
O2 C7 C6 119.7(2) . . ?
C8 C7 C6 117.2(2) . . ?
O3 C6 C5 104.44(17) . . ?
O3 C6 C7 110.06(17) . . ?
C5 C6 C7 107.7(2) . . ?
O3 C6 H6 111.5 . . ?
C5 C6 H6 111.5 . . ?
C7 C6 H6 111.5 . . ?
N1 C5 C6 106.19(18) . . ?
N1 C5 C12 115.64(18) . . ?
C6 C5 C12 114.0(2) . . ?
N1 C5 H5 106.8 . . ?
C6 C5 H5 106.8 . . ?
C12 C5 H5 106.8 . . ?
C12 C13 C14 120.7(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
O4 C18 O3 123.8(2) . . ?
O4 C18 C19 124.9(3) . . ?
O3 C18 C19 111.3(3) . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C12 C17 C16 120.6(3) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
N1 C2 C1 109.6(3) . . ?
N1 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C24 C19 C20 120.1(4) . . ?
C24 C19 C18 122.0(3) . . ?
C20 C19 C18 117.9(4) . . ?
N1 C3 C4 108.7(3) . . ?
N1 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
N1 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
O1 C1 C2 112.6(3) . . ?
O1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
O1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C10 C9 N3 108.0(3) . . ?
C10 C9 H9 126.0 . . ?
N3 C9 H9 126.0 . . ?
C9 C10 N2 109.9(3) . . ?
C9 C10 H10 125.1 . . ?
N2 C10 H10 125.1 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C19 C24 C23 121.2(5) . . ?
C19 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C21 C22 C23 125.2(5) . . ?
C21 C22 H22 117.4 . . ?
C23 C22 H22 117.4 . . ?
O1 C4 C3 112.7(3) . . ?
O1 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
O1 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C19 C20 C21 119.5(5) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C23 C24 115.9(5) . . ?
C22 C23 H23 122.0 . . ?
C24 C23 H23 122.0 . . ?
C22 C21 C20 118.1(5) . . ?
C22 C21 H21 121.0 . . ?
C20 C21 H21 121.0 . . ?

_refine_diff_density_max         0.567
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

