# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1576887'
_audit_update_record             
;
2017-09-27 deposited with the CCDC.
2017-11-21 downloaded from the CCDC.
;
_audit_creation_date             2017-02-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 N O4'
_chemical_formula_sum            'C14 H17 N O4'
_chemical_formula_weight         263.28
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   6.32903(9)
_cell_length_b                   8.54815(13)
_cell_length_c                   23.7167(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1283.11(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3176
_cell_measurement_temperature    99.97(12)
_cell_measurement_theta_max      72.5060
_cell_measurement_theta_min      5.4760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4408
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.706
_diffrn_reflns_theta_min         3.727
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0769
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926  -38.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega   24.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926   38.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   56.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926 -125.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega   49.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  150.0000 55

#__ type_ start__ end____ width___ exp.time_
  5 omega   42.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega   53.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   46.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
  9 omega   42.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
 10 omega   72.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926   57.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega  100.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
 12 omega  140.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 13 omega  115.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   97.00  165.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 68

#__ type_ start__ end____ width___ exp.time_
 15 omega  -25.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926  -77.0000  -30.0000 83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0069442000
_diffrn_orient_matrix_UB_12      -0.0734357000
_diffrn_orient_matrix_UB_13      0.0592684000
_diffrn_orient_matrix_UB_21      0.0130026000
_diffrn_orient_matrix_UB_22      0.1643666000
_diffrn_orient_matrix_UB_23      0.0264170000
_diffrn_orient_matrix_UB_31      -0.2430368000
_diffrn_orient_matrix_UB_32      0.0066833000
_diffrn_orient_matrix_UB_33      0.0031065000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                2408
_reflns_number_total             2480
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 952 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.21(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.025
_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)+(0.0361P)²+0.2771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0743
_refine_special_details          ?
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.5647(3) 0.2523(2) 0.38839(8) 0.0164(4) Uani 1 1 d . . . . .
N1 N 0.7331(2) 0.33190(18) 0.40730(6) 0.0158(3) Uani 1 1 d . . . . .
O1 O 0.3999(2) 0.31505(16) 0.37155(6) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.5845(3) 0.0771(2) 0.38452(8) 0.0187(4) Uani 1 1 d . . . . .
H2 H 0.4775 0.0239 0.3616 0.022 Uiso 1 1 calc R . . . .
O2 O 0.6560(2) -0.00655(17) 0.43430(6) 0.0233(3) Uani 1 1 d . . . . .
C3 C 0.7937(3) 0.0040(2) 0.38579(8) 0.0193(4) Uani 1 1 d . . . . .
H3 H 0.8143 -0.0909 0.3633 0.023 Uiso 1 1 calc R . . . .
O3 O 1.0435(2) 0.15408(17) 0.33802(6) 0.0202(3) Uani 1 1 d . . . . .
H3A H 1.1525 0.2058 0.3397 0.030 Uiso 1 1 calc GR . . . .
C4 C 0.9802(3) 0.1107(2) 0.39318(8) 0.0168(4) Uani 1 1 d . . . . .
H4 H 1.0952 0.0532 0.4115 0.020 Uiso 1 1 calc R . . . .
O4 O 1.4575(2) 0.77683(17) 0.31291(6) 0.0226(3) Uani 1 1 d . . . . .
C5 C 0.9202(3) 0.2517(2) 0.42940(8) 0.0174(4) Uani 1 1 d . . . . .
H5A H 0.8923 0.2170 0.4676 0.021 Uiso 1 1 calc R . . . .
H5B H 1.0378 0.3243 0.4306 0.021 Uiso 1 1 calc R . . . .
C6 C 0.7222(3) 0.5052(2) 0.41016(8) 0.0157(4) Uani 1 1 d . . . . .
H6 H 0.6016 0.5379 0.3871 0.019 Uiso 1 1 calc R . . . .
C7 C 0.9187(3) 0.5777(2) 0.38422(8) 0.0155(4) Uani 1 1 d . . . . .
C8 C 0.9443(3) 0.5763(2) 0.32588(8) 0.0179(4) Uani 1 1 d . . . . .
H8 H 0.8407 0.5299 0.3037 0.021 Uiso 1 1 calc R . . . .
C9 C 1.1192(3) 0.6420(2) 0.29985(8) 0.0186(4) Uani 1 1 d . . . . .
H9 H 1.1327 0.6397 0.2608 0.022 Uiso 1 1 calc R . . . .
C10 C 1.2745(3) 0.7116(2) 0.33309(8) 0.0175(4) Uani 1 1 d . . . . .
C11 C 1.2507(3) 0.7168(2) 0.39127(8) 0.0172(4) Uani 1 1 d . . . . .
H11 H 1.3527 0.7658 0.4133 0.021 Uiso 1 1 calc R . . . .
C12 C 1.0760(3) 0.6497(2) 0.41663(8) 0.0163(4) Uani 1 1 d . . . . .
H12 H 1.0629 0.6523 0.4557 0.020 Uiso 1 1 calc R . . . .
C13 C 0.6774(3) 0.5573(2) 0.47044(8) 0.0214(4) Uani 1 1 d . . . . .
H13A H 0.5417 0.5186 0.4820 0.032 Uiso 1 1 calc GR . . . .
H13B H 0.6776 0.6695 0.4722 0.032 Uiso 1 1 calc GR . . . .
H13C H 0.7845 0.5167 0.4951 0.032 Uiso 1 1 calc GR . . . .
C14 C 1.4948(4) 0.7690(3) 0.25355(9) 0.0256(4) Uani 1 1 d . . . . .
H14A H 1.6270 0.8186 0.2449 0.038 Uiso 1 1 calc GR . . . .
H14B H 1.3828 0.8217 0.2339 0.038 Uiso 1 1 calc GR . . . .
H14C H 1.4997 0.6615 0.2419 0.038 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
C1 N1 1.341(2) . ?
C1 O1 1.239(2) . ?
C1 C2 1.506(3) . ?
N1 C5 1.465(2) . ?
N1 C6 1.484(2) . ?
C2 H2 0.9800 . ?
C2 O2 1.453(2) . ?
C2 C3 1.465(3) . ?
O2 C3 1.446(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.502(3) . ?
O3 H3A 0.8200 . ?
O3 C4 1.418(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.528(3) . ?
O4 C10 1.372(2) . ?
O4 C14 1.429(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6 0.9800 . ?
C6 C7 1.520(3) . ?
C6 C13 1.524(3) . ?
C7 C8 1.393(3) . ?
C7 C12 1.400(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.393(3) . ?
C10 C11 1.389(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
N1 C1 C2 117.31(17) . . ?
O1 C1 N1 123.87(17) . . ?
O1 C1 C2 118.72(18) . . ?
C1 N1 C5 121.61(15) . . ?
C1 N1 C6 118.97(16) . . ?
C5 N1 C6 119.23(15) . . ?
C1 C2 H2 116.0 . . ?
O2 C2 C1 117.77(17) . . ?
O2 C2 H2 116.0 . . ?
O2 C2 C3 59.43(12) . . ?
C3 C2 C1 119.87(17) . . ?
C3 C2 H2 116.0 . . ?
C3 O2 C2 60.70(12) . . ?
C2 C3 H3 117.5 . . ?
C2 C3 C4 117.00(16) . . ?
O2 C3 C2 59.87(12) . . ?
O2 C3 H3 117.5 . . ?
O2 C3 C4 114.76(16) . . ?
C4 C3 H3 117.5 . . ?
C4 O3 H3A 109.5 . . ?
C3 C4 H4 109.3 . . ?
C3 C4 C5 110.43(16) . . ?
O3 C4 C3 105.86(15) . . ?
O3 C4 H4 109.3 . . ?
O3 C4 C5 112.51(15) . . ?
C5 C4 H4 109.3 . . ?
C10 O4 C14 117.66(16) . . ?
N1 C5 C4 111.67(16) . . ?
N1 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
N1 C6 H6 107.2 . . ?
N1 C6 C7 110.53(15) . . ?
N1 C6 C13 110.08(15) . . ?
C7 C6 H6 107.2 . . ?
C7 C6 C13 114.37(16) . . ?
C13 C6 H6 107.2 . . ?
C8 C7 C6 119.60(17) . . ?
C8 C7 C12 117.78(18) . . ?
C12 C7 C6 122.60(17) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 C7 122.13(18) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 118.96(17) . . ?
C10 C9 H9 120.5 . . ?
O4 C10 C9 124.88(17) . . ?
O4 C10 C11 115.16(17) . . ?
C11 C10 C9 119.96(18) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.36(17) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.79(17) . . ?
C11 C12 H12 119.6 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C1 N1 C5 C4 42.5(2) . . . . ?
C1 N1 C6 C7 -132.33(18) . . . . ?
C1 N1 C6 C13 100.36(19) . . . . ?
C1 C2 O2 C3 -110.0(2) . . . . ?
C1 C2 C3 O2 106.5(2) . . . . ?
C1 C2 C3 C4 2.2(3) . . . . ?
N1 C1 C2 O2 52.0(2) . . . . ?
N1 C1 C2 C3 -16.8(3) . . . . ?
N1 C6 C7 C8 73.4(2) . . . . ?
N1 C6 C7 C12 -107.8(2) . . . . ?
O1 C1 N1 C5 176.88(18) . . . . ?
O1 C1 N1 C6 1.9(3) . . . . ?
O1 C1 C2 O2 -131.45(18) . . . . ?
O1 C1 C2 C3 159.69(18) . . . . ?
C2 C1 N1 C5 -6.8(3) . . . . ?
C2 C1 N1 C6 178.23(16) . . . . ?
C2 O2 C3 C4 108.08(18) . . . . ?
C2 C3 C4 O3 -90.1(2) . . . . ?
C2 C3 C4 C5 32.0(2) . . . . ?
O2 C2 C3 C4 -104.34(18) . . . . ?
O2 C3 C4 O3 -157.39(15) . . . . ?
O2 C3 C4 C5 -35.3(2) . . . . ?
C3 C4 C5 N1 -53.2(2) . . . . ?
O3 C4 C5 N1 64.8(2) . . . . ?
O4 C10 C11 C12 -177.69(16) . . . . ?
C5 N1 C6 C7 52.6(2) . . . . ?
C5 N1 C6 C13 -74.7(2) . . . . ?
C6 N1 C5 C4 -142.56(16) . . . . ?
C6 C7 C8 C9 179.39(18) . . . . ?
C6 C7 C12 C11 -178.81(17) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
C8 C9 C10 O4 178.17(18) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 1.7(3) . . . . ?
C10 C11 C12 C7 -1.1(3) . . . . ?
C12 C7 C8 C9 0.6(3) . . . . ?
C13 C6 C7 C8 -161.66(18) . . . . ?
C13 C6 C7 C12 17.1(3) . . . . ?
C14 O4 C10 C9 -1.9(3) . . . . ?
C14 O4 C10 C11 177.46(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_fsarein
_database_code_depnum_ccdc_archive 'CCDC 1576888'
_audit_update_record             
;
2017-09-27 deposited with the CCDC.
2017-11-21 downloaded from the CCDC.
;
_audit_creation_date             2016-08-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 N O5'
_chemical_formula_sum            'C17 H19 N O5'
_chemical_formula_weight         317.33
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.66134(17)
_cell_length_b                   5.45597(10)
_cell_length_c                   14.8724(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.7727(16)
_cell_angle_gamma                90
_cell_volume                     782.25(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4618
_cell_measurement_temperature    291.84(10)
_cell_measurement_theta_max      72.5220
_cell_measurement_theta_min      5.3070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5564
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.629
_diffrn_reflns_theta_min         4.587
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.84(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0769
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -29.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926  -57.0000    0.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega   16.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926  -99.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   45.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926  -99.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926  -99.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
  5 omega  -32.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926  -38.0000 -150.0000 82

#__ type_ start__ end____ width___ exp.time_
  6 omega   48.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926   19.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   90.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   92.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  9 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  127.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
 11 omega  148.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega  132.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
 13 omega  127.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   92.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   90.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   91.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   93.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   90.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   92.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   91.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   87.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   85.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   92.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   79.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 26 omega   57.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega   44.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   44.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 66

#__ type_ start__ end____ width___ exp.time_
 29 omega   39.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 30 omega   51.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 81

#__ type_ start__ end____ width___ exp.time_
 31 omega   46.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000 -180.0000 62

#__ type_ start__ end____ width___ exp.time_
 32 omega   46.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
 33 omega    8.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926  -99.0000 -180.0000 66

#__ type_ start__ end____ width___ exp.time_
 34 omega   23.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926   57.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
 35 omega   53.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926   77.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
 36 omega   25.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926   77.0000  150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0715333000
_diffrn_orient_matrix_UB_12      -0.0843178000
_diffrn_orient_matrix_UB_13      -0.0903528000
_diffrn_orient_matrix_UB_21      -0.1328415000
_diffrn_orient_matrix_UB_22      0.1374627000
_diffrn_orient_matrix_UB_23      0.0221899000
_diffrn_orient_matrix_UB_31      0.0527699000
_diffrn_orient_matrix_UB_32      0.2317705000
_diffrn_orient_matrix_UB_33      -0.0460010000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                2875
_reflns_number_total             2925
_reflns_odcompleteness_completeness 99.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1174 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+0.0855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0904
_refine_special_details          ?
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_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
C1 C 0.6620(2) 0.1235(4) 0.68746(14) 0.0411(4) Uani 1 1 d . . . . .
C2 C 0.6233(2) 0.2022(5) 0.59206(15) 0.0483(5) Uani 1 1 d . . . . .
H2 H 0.5687 0.0840 0.5550 0.058 Uiso 1 1 calc R . . . .
C3 C 0.7106(2) 0.3680(5) 0.54302(14) 0.0498(5) Uani 1 1 d . . . . .
H3 H 0.7116 0.3478 0.4776 0.060 Uiso 1 1 calc R . . . .
C4 C 0.8426(2) 0.4375(4) 0.59379(12) 0.0420(5) Uani 1 1 d . . . . .
H4 H 0.9129 0.3112 0.5857 0.050 Uiso 1 1 calc R . . . .
C5 C 0.81989(18) 0.4658(4) 0.69371(12) 0.0352(4) Uani 1 1 d . . . . .
H5 H 0.7488 0.5918 0.6996 0.042 Uiso 1 1 calc R . . . .
C6 C 0.9580(2) 0.5734(4) 0.72775(13) 0.0392(4) Uani 1 1 d . . . . .
H6 H 0.9528 0.6662 0.7838 0.047 Uiso 1 1 calc R . . . .
C7 C 0.9917(2) 0.7359(4) 0.64686(16) 0.0465(5) Uani 1 1 d . . . . .
H7 H 0.9850 0.9103 0.6618 0.056 Uiso 1 1 calc R . . . .
C8 C 1.1840(2) 0.5031(4) 0.69355(15) 0.0455(5) Uani 1 1 d . . . . .
C9 C 1.2722(3) 0.6410(8) 0.7639(2) 0.0875(12) Uani 1 1 d . . . . .
H9A H 1.3075 0.5291 0.8097 0.131 Uiso 1 1 calc GR . . . .
H9B H 1.2171 0.7642 0.7907 0.131 Uiso 1 1 calc GR . . . .
H9C H 1.3482 0.7175 0.7363 0.131 Uiso 1 1 calc GR . . . .
C10 C 1.2588(3) 0.3071(6) 0.6459(3) 0.0799(10) Uani 1 1 d . . . . .
H10A H 1.3343 0.3786 0.6162 0.120 Uiso 1 1 calc GR . . . .
H10B H 1.1959 0.2296 0.6020 0.120 Uiso 1 1 calc GR . . . .
H10C H 1.2942 0.1874 0.6888 0.120 Uiso 1 1 calc GR . . . .
C11 C 0.8054(2) 0.1853(4) 0.82742(13) 0.0423(4) Uani 1 1 d . . . . .
H11A H 0.9053 0.1683 0.8365 0.051 Uiso 1 1 calc R . . . .
H11B H 0.7644 0.0290 0.8418 0.051 Uiso 1 1 calc R . . . .
C12 C 0.7576(2) 0.3763(4) 0.89169(12) 0.0409(5) Uani 1 1 d . . . . .
C13 C 0.6379(2) 0.5128(5) 0.87329(15) 0.0492(5) Uani 1 1 d . . . . .
H13 H 0.5853 0.4866 0.8195 0.059 Uiso 1 1 calc R . . . .
C14 C 0.5951(3) 0.6862(6) 0.93294(18) 0.0637(7) Uani 1 1 d . . . . .
H14 H 0.5148 0.7762 0.9189 0.076 Uiso 1 1 calc R . . . .
C15 C 0.6701(3) 0.7259(7) 1.0123(2) 0.0741(8) Uani 1 1 d . . . . .
H15 H 0.6410 0.8424 1.0526 0.089 Uiso 1 1 calc R . . . .
C16 C 0.7890(4) 0.5936(8) 1.03271(19) 0.0834(10) Uani 1 1 d . . . . .
H16 H 0.8402 0.6213 1.0869 0.100 Uiso 1 1 calc R . . . .
C17 C 0.8335(3) 0.4186(7) 0.97303(15) 0.0651(7) Uani 1 1 d . . . . .
H17 H 0.9140 0.3297 0.9875 0.078 Uiso 1 1 calc R . . . .
N1 N 0.77007(16) 0.2404(3) 0.73237(10) 0.0364(4) Uani 1 1 d . . . . .
O1 O 0.59858(18) -0.0459(3) 0.71959(12) 0.0599(5) Uani 1 1 d . . . . .
O2 O 0.58536(15) 0.4570(4) 0.57883(10) 0.0534(4) Uani 1 1 d . . . . .
O3 O 0.89762(17) 0.6736(4) 0.57333(11) 0.0568(5) Uani 1 1 d . . . . .
O4 O 1.06588(14) 0.3960(3) 0.73217(10) 0.0430(3) Uani 1 1 d . . . . .
O5 O 1.12730(16) 0.6730(4) 0.62896(11) 0.0573(5) 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 1.506(3) . ?
C1 N1 1.361(3) . ?
C1 O1 1.223(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.464(3) . ?
C2 O2 1.448(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.488(3) . ?
C3 O2 1.438(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.524(2) . ?
C4 O3 1.434(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.514(3) . ?
C5 N1 1.453(2) . ?
C6 H6 0.9800 . ?
C6 C7 1.546(3) . ?
C6 O4 1.421(2) . ?
C7 H7 0.9800 . ?
C7 O3 1.417(3) . ?
C7 O5 1.397(3) . ?
C8 C9 1.507(4) . ?
C8 C10 1.495(4) . ?
C8 O4 1.435(2) . ?
C8 O5 1.419(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.507(3) . ?
C11 N1 1.464(2) . ?
C12 C13 1.388(3) . ?
C12 C17 1.392(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.362(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.374(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.391(5) . ?
C17 H17 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
N1 C1 C2 117.61(18) . . ?
O1 C1 C2 118.9(2) . . ?
O1 C1 N1 123.4(2) . . ?
C1 C2 H2 115.7 . . ?
C3 C2 C1 122.02(18) . . ?
C3 C2 H2 115.7 . . ?
O2 C2 C1 116.54(19) . . ?
O2 C2 H2 115.7 . . ?
O2 C2 C3 59.22(16) . . ?
C2 C3 H3 118.0 . . ?
C2 C3 C4 114.04(18) . . ?
C4 C3 H3 118.0 . . ?
O2 C3 C2 59.84(15) . . ?
O2 C3 H3 118.0 . . ?
O2 C3 C4 116.12(19) . . ?
C3 C4 H4 109.7 . . ?
C3 C4 C5 110.29(16) . . ?
C5 C4 H4 109.7 . . ?
O3 C4 C3 115.99(19) . . ?
O3 C4 H4 109.7 . . ?
O3 C4 C5 101.24(17) . . ?
C4 C5 H5 107.8 . . ?
C6 C5 C4 100.65(15) . . ?
C6 C5 H5 107.8 . . ?
N1 C5 C4 111.88(16) . . ?
N1 C5 H5 107.8 . . ?
N1 C5 C6 120.23(16) . . ?
C5 C6 H6 113.0 . . ?
C5 C6 C7 100.85(16) . . ?
C7 C6 H6 113.0 . . ?
O4 C6 C5 112.28(17) . . ?
O4 C6 H6 113.0 . . ?
O4 C6 C7 103.60(15) . . ?
C6 C7 H7 111.1 . . ?
O3 C7 C6 107.79(18) . . ?
O3 C7 H7 111.1 . . ?
O5 C7 C6 104.80(17) . . ?
O5 C7 H7 111.1 . . ?
O5 C7 O3 110.9(2) . . ?
C10 C8 C9 114.7(3) . . ?
O4 C8 C9 110.7(2) . . ?
O4 C8 C10 108.7(2) . . ?
O5 C8 C9 108.6(2) . . ?
O5 C8 C10 108.8(2) . . ?
O5 C8 O4 104.80(16) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
N1 C11 H11A 108.7 . . ?
N1 C11 H11B 108.7 . . ?
N1 C11 C12 114.12(17) . . ?
C13 C12 C11 122.15(18) . . ?
C13 C12 C17 117.8(2) . . ?
C17 C12 C11 120.0(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 120.1(3) . . ?
C16 C17 H17 120.0 . . ?
C1 N1 C5 117.78(16) . . ?
C1 N1 C11 120.02(17) . . ?
C5 N1 C11 119.61(16) . . ?
C3 O2 C2 60.95(16) . . ?
C7 O3 C4 106.25(16) . . ?
C6 O4 C8 107.72(16) . . ?
C7 O5 C8 110.89(16) . . ?

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
C1 C2 C3 C4 3.4(3) . . . . ?
C1 C2 C3 O2 -103.9(2) . . . . ?
C1 C2 O2 C3 113.1(2) . . . . ?
C2 C1 N1 C5 13.5(3) . . . . ?
C2 C1 N1 C11 175.19(18) . . . . ?
C2 C3 C4 C5 -36.4(3) . . . . ?
C2 C3 C4 O3 -150.7(2) . . . . ?
C3 C4 C5 C6 -171.4(2) . . . . ?
C3 C4 C5 N1 59.7(2) . . . . ?
C3 C4 O3 C7 160.88(18) . . . . ?
C4 C3 O2 C2 -103.9(2) . . . . ?
C4 C5 C6 C7 35.45(19) . . . . ?
C4 C5 C6 O4 -74.27(19) . . . . ?
C4 C5 N1 C1 -48.4(2) . . . . ?
C4 C5 N1 C11 149.79(17) . . . . ?
C5 C4 O3 C7 41.5(2) . . . . ?
C5 C6 C7 O3 -11.8(2) . . . . ?
C5 C6 C7 O5 -129.96(19) . . . . ?
C5 C6 O4 C8 134.25(17) . . . . ?
C6 C5 N1 C1 -166.13(17) . . . . ?
C6 C5 N1 C11 32.1(2) . . . . ?
C6 C7 O3 C4 -18.7(2) . . . . ?
C6 C7 O5 C8 -4.1(3) . . . . ?
C7 C6 O4 C8 26.3(2) . . . . ?
C9 C8 O4 C6 87.7(3) . . . . ?
C9 C8 O5 C7 -98.2(3) . . . . ?
C10 C8 O4 C6 -145.5(2) . . . . ?
C10 C8 O5 C7 136.3(2) . . . . ?
C11 C12 C13 C14 179.7(2) . . . . ?
C11 C12 C17 C16 -179.6(3) . . . . ?
C12 C11 N1 C1 -102.7(2) . . . . ?
C12 C11 N1 C5 58.7(2) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C12 C17 C16 -0.3(4) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C17 -0.1(6) . . . . ?
C15 C16 C17 C12 0.1(5) . . . . ?
C17 C12 C13 C14 0.4(4) . . . . ?
N1 C1 C2 C3 10.0(3) . . . . ?
N1 C1 C2 O2 -58.7(2) . . . . ?
N1 C5 C6 C7 158.71(17) . . . . ?
N1 C5 C6 O4 49.0(2) . . . . ?
N1 C11 C12 C13 31.8(3) . . . . ?
N1 C11 C12 C17 -148.9(2) . . . . ?
O1 C1 C2 C3 -167.6(2) . . . . ?
O1 C1 C2 O2 123.6(2) . . . . ?
O1 C1 N1 C5 -168.96(19) . . . . ?
O1 C1 N1 C11 -7.3(3) . . . . ?
O2 C2 C3 C4 107.4(2) . . . . ?
O2 C3 C4 C5 30.4(3) . . . . ?
O2 C3 C4 O3 -83.9(2) . . . . ?
O3 C4 C5 C6 -48.08(18) . . . . ?
O3 C4 C5 N1 -176.95(15) . . . . ?
O3 C7 O5 C8 -120.1(2) . . . . ?
O4 C6 C7 O3 104.50(18) . . . . ?
O4 C6 C7 O5 -13.6(2) . . . . ?
O4 C8 O5 C7 20.2(3) . . . . ?
O5 C7 O3 C4 95.4(2) . . . . ?
O5 C8 O4 C6 -29.3(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1576889'
_audit_update_record             
;
2017-09-27 deposited with the CCDC.
2017-11-21 downloaded from the CCDC.
;
_audit_creation_date             2017-02-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 N O4'
_chemical_formula_sum            'C14 H17 N O4'
_chemical_formula_weight         263.28
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.38939(11)
_cell_length_b                   7.59037(13)
_cell_length_c                   26.8562(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1302.47(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6362
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.6180
_cell_measurement_theta_min      5.9900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8224
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.734
_diffrn_reflns_theta_min         6.059
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0769
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926  -38.0000  -60.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega   63.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926   19.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega    2.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926  -99.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega   45.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926 -125.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega   43.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926 -125.0000   60.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega   60.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   53.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   60.0000 59

#__ type_ start__ end____ width___ exp.time_
  8 omega   48.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
  9 omega   41.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   30.0000 78

#__ type_ start__ end____ width___ exp.time_
 10 omega   93.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 83

#__ type_ start__ end____ width___ exp.time_
 11 omega  143.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 12 omega  113.00  148.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 13 omega   82.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -60.0000 67

#__ type_ start__ end____ width___ exp.time_
 14 omega  108.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   61.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
 16 omega  -26.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926  -19.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
 17 omega   44.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
 18 omega   44.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
 19 omega   46.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
 20 omega   46.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  -30.0000 56

#__ type_ start__ end____ width___ exp.time_
 21 omega   47.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000   60.0000 63

#__ type_ start__ end____ width___ exp.time_
 22 omega   41.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
 23 omega   39.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 24 omega  -29.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926  -57.0000   60.0000 78

#__ type_ start__ end____ width___ exp.time_
 25 omega  -28.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8926  -57.0000 -180.0000 66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0141163000
_diffrn_orient_matrix_UB_12      -0.1781790000
_diffrn_orient_matrix_UB_13      -0.0272792000
_diffrn_orient_matrix_UB_21      0.0127056000
_diffrn_orient_matrix_UB_22      -0.0960467000
_diffrn_orient_matrix_UB_23      0.0504337000
_diffrn_orient_matrix_UB_31      -0.2403615000
_diffrn_orient_matrix_UB_32      -0.0155515000
_diffrn_orient_matrix_UB_33      0.0011160000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2525
_reflns_number_total             2564
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 998 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2564
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.2133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0785
_refine_special_details          ?
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.5614(3) 0.5044(2) 0.32546(6) 0.0185(4) Uani 1 1 d . . . . .
N1 N 0.3972(2) 0.51823(19) 0.35600(5) 0.0189(3) Uani 1 1 d . . . . .
O1 O 0.72537(19) 0.59064(17) 0.33073(5) 0.0231(3) Uani 1 1 d . . . . .
C2 C 0.5391(3) 0.3862(2) 0.28094(7) 0.0216(4) Uani 1 1 d . . . . .
H2 H 0.6483 0.3995 0.2545 0.026 Uiso 1 1 calc R . . . .
O2 O 0.4559(2) 0.21108(17) 0.28760(5) 0.0255(3) Uani 1 1 d . . . . .
C3 C 0.3283(3) 0.3421(2) 0.26350(7) 0.0229(4) Uani 1 1 d . . . . .
H3 H 0.3067 0.3307 0.2268 0.027 Uiso 1 1 calc R . . . .
O3 O 0.0819(2) 0.56676(18) 0.27470(5) 0.0257(3) Uani 1 1 d . . . . .
H3A H -0.0330 0.5960 0.2874 0.039 Uiso 1 1 calc GR . . . .
C4 C 0.1457(3) 0.4015(2) 0.29426(7) 0.0221(4) Uani 1 1 d . . . . .
H4 H 0.0287 0.3150 0.2904 0.026 Uiso 1 1 calc R . . . .
O4 O 0.3982(2) 0.35939(17) 0.59010(5) 0.0245(3) Uani 1 1 d . . . . .
C5 C 0.2080(3) 0.4116(2) 0.34902(7) 0.0212(4) Uani 1 1 d . . . . .
H5A H 0.0917 0.4638 0.3684 0.025 Uiso 1 1 calc R . . . .
H5B H 0.2331 0.2912 0.3618 0.025 Uiso 1 1 calc R . . . .
C6 C 0.3994(3) 0.6543(2) 0.39561(7) 0.0208(4) Uani 1 1 d . . . . .
H6 H 0.5404 0.7113 0.3941 0.025 Uiso 1 1 calc R . . . .
C7 C 0.3816(3) 0.5718(2) 0.44698(6) 0.0190(3) Uani 1 1 d . . . . .
C8 C 0.5422(3) 0.4600(2) 0.46309(7) 0.0222(4) Uani 1 1 d . . . . .
H8 H 0.6526 0.4311 0.4408 0.027 Uiso 1 1 calc R . . . .
C9 C 0.5435(3) 0.3906(2) 0.51075(7) 0.0222(4) Uani 1 1 d . . . . .
H9 H 0.6541 0.3153 0.5211 0.027 Uiso 1 1 calc R . . . .
C10 C 0.3816(3) 0.4319(2) 0.54358(6) 0.0200(4) Uani 1 1 d . . . . .
C11 C 0.2188(3) 0.5392(2) 0.52808(7) 0.0208(4) Uani 1 1 d . . . . .
H11 H 0.1068 0.5655 0.5501 0.025 Uiso 1 1 calc R . . . .
C12 C 0.2199(3) 0.6088(2) 0.47988(7) 0.0205(4) Uani 1 1 d . . . . .
H12 H 0.1081 0.6827 0.4695 0.025 Uiso 1 1 calc R . . . .
C13 C 0.2409(3) 0.7979(3) 0.38372(7) 0.0270(4) Uani 1 1 d . . . . .
H13A H 0.2705 0.8469 0.3507 0.040 Uiso 1 1 calc GR . . . .
H13B H 0.2505 0.8915 0.4088 0.040 Uiso 1 1 calc GR . . . .
H13C H 0.0995 0.7477 0.3840 0.040 Uiso 1 1 calc GR . . . .
C14 C 0.2489(3) 0.4143(3) 0.62658(7) 0.0298(4) Uani 1 1 d . . . . .
H14A H 0.1090 0.3745 0.6167 0.045 Uiso 1 1 calc GR . . . .
H14B H 0.2501 0.5431 0.6291 0.045 Uiso 1 1 calc GR . . . .
H14C H 0.2853 0.3630 0.6589 0.045 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
C1 N1 1.336(2) . ?
C1 O1 1.244(2) . ?
C1 C2 1.501(2) . ?
N1 C5 1.467(2) . ?
N1 C6 1.483(2) . ?
C2 H2 1.0000 . ?
C2 O2 1.442(2) . ?
C2 C3 1.465(2) . ?
O2 C3 1.440(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.499(3) . ?
O3 H3A 0.8400 . ?
O3 C4 1.419(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.525(2) . ?
O4 C10 1.369(2) . ?
O4 C14 1.430(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6 1.0000 . ?
C6 C7 1.520(2) . ?
C6 C13 1.522(3) . ?
C7 C8 1.400(3) . ?
C7 C12 1.388(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.395(3) . ?
C10 C11 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.398(2) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
N1 C1 C2 117.49(15) . . ?
O1 C1 N1 123.37(16) . . ?
O1 C1 C2 119.02(16) . . ?
C1 N1 C5 121.68(14) . . ?
C1 N1 C6 119.22(15) . . ?
C5 N1 C6 118.93(14) . . ?
C1 C2 H2 116.0 . . ?
O2 C2 C1 119.13(15) . . ?
O2 C2 H2 116.0 . . ?
O2 C2 C3 59.36(12) . . ?
C3 C2 C1 118.57(15) . . ?
C3 C2 H2 116.0 . . ?
C3 O2 C2 61.09(11) . . ?
C2 C3 H3 117.5 . . ?
C2 C3 C4 118.09(16) . . ?
O2 C3 C2 59.55(12) . . ?
O2 C3 H3 117.5 . . ?
O2 C3 C4 113.63(16) . . ?
C4 C3 H3 117.5 . . ?
C4 O3 H3A 109.5 . . ?
C3 C4 H4 109.1 . . ?
C3 C4 C5 110.07(15) . . ?
O3 C4 C3 106.57(15) . . ?
O3 C4 H4 109.1 . . ?
O3 C4 C5 112.78(15) . . ?
C5 C4 H4 109.1 . . ?
C10 O4 C14 117.16(14) . . ?
N1 C5 C4 111.49(14) . . ?
N1 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N1 C6 H6 106.4 . . ?
N1 C6 C7 111.32(14) . . ?
N1 C6 C13 110.01(15) . . ?
C7 C6 H6 106.4 . . ?
C7 C6 C13 115.83(15) . . ?
C13 C6 H6 106.4 . . ?
C8 C7 C6 118.38(16) . . ?
C12 C7 C6 123.39(16) . . ?
C12 C7 C8 118.13(17) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.37(17) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.66(16) . . ?
C10 C9 H9 120.2 . . ?
O4 C10 C9 115.42(16) . . ?
O4 C10 C11 124.65(16) . . ?
C11 C10 C9 119.93(16) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.78(16) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 121.10(16) . . ?
C7 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C1 N1 C5 C4 -42.5(2) . . . . ?
C1 N1 C6 C7 -120.01(17) . . . . ?
C1 N1 C6 C13 110.21(19) . . . . ?
C1 C2 O2 C3 107.84(18) . . . . ?
C1 C2 C3 O2 -108.76(18) . . . . ?
C1 C2 C3 C4 -6.4(3) . . . . ?
N1 C1 C2 O2 -48.1(2) . . . . ?
N1 C1 C2 C3 20.8(3) . . . . ?
N1 C6 C7 C8 63.4(2) . . . . ?
N1 C6 C7 C12 -120.14(18) . . . . ?
O1 C1 N1 C5 -178.87(15) . . . . ?
O1 C1 N1 C6 5.9(3) . . . . ?
O1 C1 C2 O2 135.56(16) . . . . ?
O1 C1 C2 C3 -155.59(17) . . . . ?
C2 C1 N1 C5 5.0(2) . . . . ?
C2 C1 N1 C6 -170.24(15) . . . . ?
C2 O2 C3 C4 -109.81(17) . . . . ?
C2 C3 C4 O3 93.12(19) . . . . ?
C2 C3 C4 C5 -29.5(2) . . . . ?
O2 C2 C3 C4 102.32(18) . . . . ?
O2 C3 C4 O3 159.95(14) . . . . ?
O2 C3 C4 C5 37.4(2) . . . . ?
C3 C4 C5 N1 52.6(2) . . . . ?
O3 C4 C5 N1 -66.26(19) . . . . ?
O4 C10 C11 C12 178.81(16) . . . . ?
C5 N1 C6 C7 64.7(2) . . . . ?
C5 N1 C6 C13 -65.1(2) . . . . ?
C6 N1 C5 C4 132.67(16) . . . . ?
C6 C7 C8 C9 175.26(17) . . . . ?
C6 C7 C12 C11 -175.30(16) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C7 C12 C11 1.1(3) . . . . ?
C8 C9 C10 O4 -179.01(16) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C10 C11 C12 C7 0.2(3) . . . . ?
C12 C7 C8 C9 -1.4(3) . . . . ?
C13 C6 C7 C8 -169.91(17) . . . . ?
C13 C6 C7 C12 6.5(3) . . . . ?
C14 O4 C10 C9 173.01(17) . . . . ?
C14 O4 C10 C11 -7.2(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
