# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_mo_chen2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1547520'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;
_audit_creation_date             2017-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H21 N O5'
_chemical_formula_sum            'C19 H21 N O5'
_chemical_formula_weight         343.37
_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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.2521(5)
_cell_length_b                   9.8028(5)
_cell_length_c                   9.9294(5)
_cell_angle_alpha                75.6790(10)
_cell_angle_beta                 88.544(2)
_cell_angle_gamma                79.757(2)
_cell_volume                     858.51(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.24
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27853
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.18
_diffrn_ambient_temperature      120.05
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3506
_reflns_number_total             3915
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.151
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0633P)²+0.2298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1212
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C15(H15A,H15B), C17(H17A,H17B), C16(H16A,H16B), C18(H18A,
 H18B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C6(H6), C8(H8), C7(H7)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O5 O 0.29936(9) 0.15160(9) 0.98661(8) 0.0195(2) Uani 1 d . . .
O3 O 0.15191(9) 0.03720(9) 0.74748(8) 0.0194(2) Uani 1 d . . .
O4 O 0.05478(9) 0.23249(9) 0.95608(9) 0.0222(2) Uani 1 d . . .
O2 O 0.12472(11) 0.11192(10) 0.51433(9) 0.0260(2) Uani 1 d . . .
O1 O 0.28064(10) 0.46666(9) 0.60789(8) 0.0205(2) Uani 1 d . . .
N1 N 0.26705(12) 0.41898(11) 0.75366(10) 0.0208(2) Uani 1 d . . .
C10 C 0.15142(12) 0.13228(12) 0.62486(12) 0.0169(2) Uani 1 d . . .
C13 C 0.17871(13) 0.22392(12) 0.91594(12) 0.0171(2) Uani 1 d . . .
C14 C 0.28001(13) 0.06515(12) 1.12771(11) 0.0179(2) Uani 1 d . . .
H14 H 0.2021 0.1195 1.1755 0.021 Uiso 1 calc . . R
C5 C 0.37292(14) 0.44580(13) 0.32961(13) 0.0222(3) Uani 1 d . . .
H5 H 0.4540 0.4503 0.3842 0.027 Uiso 1 calc . . R
C19 C 0.23519(14) -0.07424(13) 1.11953(13) 0.0215(3) Uani 1 d . . .
H19A H 0.3062 -0.1230 1.0628 0.026 Uiso 1 calc . . R
H19B H 0.1370 -0.0542 1.0742 0.026 Uiso 1 calc . . R
C15 C 0.42609(13) 0.04271(14) 1.20273(13) 0.0222(3) Uani 1 d . . .
H15A H 0.4470 0.1360 1.2109 0.027 Uiso 1 calc . . R
H15B H 0.5054 0.0005 1.1487 0.027 Uiso 1 calc . . R
C9 C 0.12597(14) 0.40035(13) 0.31361(13) 0.0229(3) Uani 1 d . . .
H9 H 0.0394 0.3731 0.3573 0.028 Uiso 1 calc . . R
C2 C 0.19261(12) 0.26496(12) 0.64437(12) 0.0166(2) Uani 1 d . . .
C4 C 0.24559(13) 0.40594(12) 0.39368(12) 0.0184(2) Uani 1 d . . .
C17 C 0.37931(15) -0.19791(14) 1.34039(13) 0.0253(3) Uani 1 d . . .
H17A H 0.3736 -0.2583 1.4357 0.030 Uiso 1 calc . . R
H17B H 0.4553 -0.2498 1.2903 0.030 Uiso 1 calc . . R
C1 C 0.21529(12) 0.30063(12) 0.77165(12) 0.0169(2) Uani 1 d . . .
C16 C 0.42240(14) -0.05685(14) 1.34759(13) 0.0247(3) Uani 1 d . . .
H16A H 0.5205 -0.0761 1.3930 0.030 Uiso 1 calc . . R
H16B H 0.3510 -0.0093 1.4049 0.030 Uiso 1 calc . . R
C18 C 0.23106(14) -0.17125(14) 1.26561(13) 0.0244(3) Uani 1 d . . .
H18A H 0.1539 -0.1259 1.3195 0.029 Uiso 1 calc . . R
H18B H 0.2062 -0.2636 1.2593 0.029 Uiso 1 calc . . R
C3 C 0.23628(12) 0.37303(12) 0.54571(12) 0.0170(2) Uani 1 d . . .
C11 C 0.11554(14) -0.10125(12) 0.74491(13) 0.0205(3) Uani 1 d . . .
H11A H 0.0508 -0.0898 0.6635 0.025 Uiso 1 calc . . R
H11B H 0.0619 -0.1378 0.8299 0.025 Uiso 1 calc . . R
C12 C 0.25313(16) -0.20654(14) 0.73690(16) 0.0312(3) Uani 1 d . . .
H12A H 0.3053 -0.1709 0.6519 0.047 Uiso 1 calc . . GR
H12B H 0.2273 -0.2989 0.7355 0.047 Uiso 1 calc . . GR
H12C H 0.3166 -0.2185 0.8181 0.047 Uiso 1 calc . . GR
C6 C 0.38024(16) 0.47879(14) 0.18585(13) 0.0277(3) Uani 1 d . . .
H6 H 0.4670 0.5051 0.1418 0.033 Uiso 1 calc . . R
C8 C 0.13448(16) 0.43492(14) 0.16998(13) 0.0276(3) Uani 1 d . . .
H8 H 0.0531 0.4321 0.1149 0.033 Uiso 1 calc . . R
C7 C 0.26148(17) 0.47361(14) 0.10620(13) 0.0297(3) Uani 1 d . . .
H7 H 0.2670 0.4966 0.0077 0.036 Uiso 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
O5 C13 1.3241(14) . ?
O5 C14 1.4721(13) . ?
O3 C10 1.3374(14) . ?
O3 C11 1.4615(13) . ?
O4 C13 1.1998(15) . ?
O2 C10 1.2020(14) . ?
O1 N1 1.4164(12) . ?
O1 C3 1.3488(14) . ?
N1 C1 1.3030(15) . ?
C10 C2 1.4762(15) . ?
C13 C1 1.5052(15) . ?
C14 C19 1.5178(16) . ?
C14 C15 1.5147(16) . ?
C5 C4 1.3957(17) . ?
C5 C6 1.3860(17) . ?
C19 C18 1.5288(16) . ?
C15 C16 1.5289(17) . ?
C9 C4 1.3956(17) . ?
C9 C8 1.3855(17) . ?
C2 C1 1.4220(15) . ?
C2 C3 1.3653(16) . ?
C4 C3 1.4672(15) . ?
C17 C16 1.5240(19) . ?
C17 C18 1.5261(18) . ?
C11 C12 1.5034(18) . ?
C6 C7 1.385(2) . ?
C8 C7 1.388(2) . ?

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
C13 O5 C14 116.91(9) . . ?
C10 O3 C11 116.55(9) . . ?
C3 O1 N1 109.22(9) . . ?
C1 N1 O1 104.84(9) . . ?
O3 C10 C2 110.08(9) . . ?
O2 C10 O3 125.15(11) . . ?
O2 C10 C2 124.75(11) . . ?
O5 C13 C1 110.77(9) . . ?
O4 C13 O5 127.31(11) . . ?
O4 C13 C1 121.91(10) . . ?
O5 C14 C19 109.71(9) . . ?
O5 C14 C15 105.71(9) . . ?
C15 C14 C19 112.79(10) . . ?
C6 C5 C4 119.55(12) . . ?
C14 C19 C18 109.92(10) . . ?
C14 C15 C16 110.14(10) . . ?
C8 C9 C4 119.49(12) . . ?
C1 C2 C10 127.87(10) . . ?
C3 C2 C10 127.81(10) . . ?
C3 C2 C1 103.82(10) . . ?
C5 C4 C3 119.82(11) . . ?
C9 C4 C5 120.27(11) . . ?
C9 C4 C3 119.89(11) . . ?
C16 C17 C18 110.56(10) . . ?
N1 C1 C13 119.34(10) . . ?
N1 C1 C2 112.71(10) . . ?
C2 C1 C13 127.85(10) . . ?
C17 C16 C15 111.36(10) . . ?
C17 C18 C19 110.69(10) . . ?
O1 C3 C2 109.42(10) . . ?
O1 C3 C4 116.11(10) . . ?
C2 C3 C4 134.47(11) . . ?
O3 C11 C12 110.29(10) . . ?
C7 C6 C5 120.26(13) . . ?
C9 C8 C7 120.27(12) . . ?
C6 C7 C8 120.16(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
