# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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 
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data_sa4435
_database_code_depnum_ccdc_archive 'CCDC 1455389'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;
_audit_creation_date             2015-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N O6'
_chemical_formula_sum            'C14 H19 N O6'
_chemical_formula_weight         297.30
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   5.6525(14)
_cell_length_b                   7.679(2)
_cell_length_c                   32.488(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1410.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4437
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4726
_cell_measurement_theta_min      2.5077
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            9818
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         3.252
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 9.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.1050
	          2theta: -20.0354
scan:
	Number of images: 300
	           Slice: -110.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 9.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.1050
	          2theta: -20.0354
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             1914
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0462
_diffrn_orient_matrix_UB_12      0.1708
_diffrn_orient_matrix_UB_13      0.0023
_diffrn_orient_matrix_UB_21      -0.0252
_diffrn_orient_matrix_UB_22      -0.0051
_diffrn_orient_matrix_UB_23      -0.1277
_diffrn_orient_matrix_UB_31      -0.0291
_diffrn_orient_matrix_UB_32      -0.0080
_diffrn_orient_matrix_UB_33      0.0061
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3104
_reflns_number_total             3185
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1149 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.117
_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)+(0.0276P)²+0.2616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0733
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3A), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O1 O 0.7385(2) 0.18507(17) 0.26747(4) 0.0232(3) Uani 1 1 d . . . . .
O2 O 0.3504(2) 0.24240(19) 0.31562(4) 0.0254(3) Uani 1 1 d . . . . .
O3 O 0.8221(2) 0.53570(17) 0.24987(4) 0.0218(3) Uani 1 1 d . . . . .
O4 O 0.9771(3) 0.7897(2) 0.30834(5) 0.0355(4) Uani 1 1 d . . . . .
O5 O 1.0800(3) 0.60641(19) 0.38008(4) 0.0309(3) Uani 1 1 d . . . . .
O6 O 0.8409(2) 0.48479(17) 0.42792(4) 0.0259(3) Uani 1 1 d . . . . .
N1 N 0.7743(3) 0.42819(19) 0.36170(4) 0.0199(3) Uani 1 1 d . . . . .
C1 C 0.8444(3) 0.4140(2) 0.31822(5) 0.0183(3) Uani 1 1 d . . . . .
H1A H 1.0158 0.4300 0.3158 0.022 Uiso 1 1 calc R . . . .
C2 C 0.7810(3) 0.2220(2) 0.30962(5) 0.0192(4) Uani 1 1 d . . . . .
H2A H 0.9099 0.1476 0.3195 0.023 Uiso 1 1 calc R . . . .
C3 C 0.5594(3) 0.1867(2) 0.33546(5) 0.0207(4) Uani 1 1 d . . . . .
H3A H 0.5489 0.0631 0.3427 0.025 Uiso 1 1 calc R . . . .
C4 C 0.5959(3) 0.2976(3) 0.37391(6) 0.0238(4) Uani 1 1 d . . . . .
H4A H 0.4494 0.3536 0.3821 0.029 Uiso 1 1 calc R . . . .
H4B H 0.6530 0.2271 0.3966 0.029 Uiso 1 1 calc R . . . .
C5 C 0.7163(3) 0.5450(2) 0.29011(5) 0.0201(4) Uani 1 1 d . . . . .
H5 H 0.5484 0.5141 0.2882 0.024 Uiso 1 1 calc R . . . .
C6 C 0.7399(4) 0.7323(2) 0.30427(6) 0.0291(4) Uani 1 1 d . . . . .
H6A H 0.6593 0.8071 0.2847 0.035 Uiso 1 1 calc R . . . .
H6B H 0.6610 0.7448 0.3306 0.035 Uiso 1 1 calc R . . . .
C7 C 0.9121(3) 0.5130(2) 0.38874(5) 0.0223(4) Uani 1 1 d . . . . .
C8 C 0.9937(4) 0.5571(3) 0.45901(6) 0.0279(4) Uani 1 1 d . . . . .
H8A H 1.0158 0.6807 0.4542 0.033 Uiso 1 1 calc R . . . .
H8B H 1.1473 0.5009 0.4580 0.033 Uiso 1 1 calc R . . . .
C9 C 0.8822(3) 0.5286(2) 0.50061(6) 0.0243(4) Uani 1 1 d . . . . .
C10 C 0.6801(4) 0.4295(3) 0.50654(6) 0.0307(4) Uani 1 1 d . . . . .
H10 H 0.6069 0.3761 0.4842 0.037 Uiso 1 1 calc R . . . .
C11 C 0.5867(4) 0.4102(3) 0.54600(7) 0.0362(5) Uani 1 1 d . . . . .
H11 H 0.4517 0.3429 0.5498 0.043 Uiso 1 1 calc R . . . .
C12 C 0.6919(4) 0.4897(3) 0.57945(6) 0.0360(5) Uani 1 1 d . . . . .
H12 H 0.6281 0.4766 0.6056 0.043 Uiso 1 1 calc R . . . .
C13 C 0.8929(4) 0.5889(3) 0.57359(6) 0.0360(5) Uani 1 1 d . . . . .
H13 H 0.9650 0.6428 0.5959 0.043 Uiso 1 1 calc R . . . .
C14 C 0.9874(4) 0.6082(3) 0.53461(6) 0.0306(5) Uani 1 1 d . . . . .
H14 H 1.1230 0.6751 0.5310 0.037 Uiso 1 1 calc R . . . .
H4 H 1.036(5) 0.739(4) 0.3289(8) 0.044(8) Uiso 1 1 d . . . . .
H3 H 0.824(5) 0.434(4) 0.2423(8) 0.043(7) Uiso 1 1 d . . . . .
H1 H 0.862(5) 0.134(3) 0.2576(8) 0.045(8) Uiso 1 1 d . . . . .
H2 H 0.335(5) 0.183(4) 0.2941(8) 0.040(7) Uiso 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
O1 C2 1.419(2) . ?
O1 H1 0.87(3) . ?
O2 C3 1.412(2) . ?
O2 H2 0.84(3) . ?
O3 C5 1.439(2) . ?
O3 H3 0.82(3) . ?
O4 C6 1.417(3) . ?
O4 H4 0.84(3) . ?
O5 C7 1.222(2) . ?
O6 C7 1.353(2) . ?
O6 C8 1.440(2) . ?
N1 C1 1.471(2) . ?
N1 C4 1.476(2) . ?
N1 C7 1.342(2) . ?
C1 H1A 0.9800 . ?
C1 C2 1.542(2) . ?
C1 C5 1.540(2) . ?
C2 H2A 0.9800 . ?
C2 C3 1.532(2) . ?
C3 H3A 0.9800 . ?
C3 C4 1.526(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5 0.9800 . ?
C5 C6 1.516(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.507(3) . ?
C9 C10 1.386(3) . ?
C9 C14 1.395(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.394(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(3) . ?
C14 H14 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
C2 O1 H1 108.2(18) . . ?
C3 O2 H2 107.5(18) . . ?
C5 O3 H3 109.0(19) . . ?
C6 O4 H4 107.5(19) . . ?
C7 O6 C8 114.83(15) . . ?
C1 N1 C4 113.05(14) . . ?
C7 N1 C1 120.54(15) . . ?
C7 N1 C4 123.36(14) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 C2 100.50(13) . . ?
N1 C1 C5 113.23(14) . . ?
C2 C1 H1A 109.6 . . ?
C5 C1 H1A 109.6 . . ?
C5 C1 C2 114.09(15) . . ?
O1 C2 C1 113.89(14) . . ?
O1 C2 H2A 109.0 . . ?
O1 C2 C3 110.78(14) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 C1 105.06(14) . . ?
C3 C2 H2A 109.0 . . ?
O2 C3 C2 112.36(14) . . ?
O2 C3 H3A 110.6 . . ?
O2 C3 C4 108.53(15) . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 C2 103.83(14) . . ?
C4 C3 H3A 110.6 . . ?
N1 C4 C3 104.56(14) . . ?
N1 C4 H4A 110.8 . . ?
N1 C4 H4B 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
O3 C5 C1 108.11(14) . . ?
O3 C5 H5 109.5 . . ?
O3 C5 C6 106.64(14) . . ?
C1 C5 H5 109.5 . . ?
C6 C5 C1 113.50(15) . . ?
C6 C5 H5 109.5 . . ?
O4 C6 C5 113.98(16) . . ?
O4 C6 H6A 108.8 . . ?
O4 C6 H6B 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O5 C7 O6 122.78(17) . . ?
O5 C7 N1 125.77(17) . . ?
N1 C7 O6 111.44(15) . . ?
O6 C8 H8A 109.9 . . ?
O6 C8 H8B 109.9 . . ?
O6 C8 C9 108.80(16) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
C10 C9 C8 123.29(17) . . ?
C10 C9 C14 118.79(18) . . ?
C14 C9 C8 117.91(17) . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.90(19) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.9(2) . . ?
C13 C14 H14 119.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O5 0.84(3) 1.96(3) 2.784(2) 164(3) .
O3 H3 O1 0.82(3) 2.13(3) 2.793(2) 137(2) .
O3 H3 O4 0.82(3) 2.28(3) 2.904(2) 133(2) 3_745
O1 H1 O3 0.87(3) 1.95(3) 2.793(2) 164(3) 3_745
O1 H1 O4 0.87(3) 2.62(3) 3.049(2) 112(2) 3_745
O2 H2 O3 0.84(3) 2.03(3) 2.8278(19) 159(2) 3_645

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
O1 C2 C3 O2 -40.59(19) . . . . ?
O1 C2 C3 C4 -157.67(14) . . . . ?
O2 C3 C4 N1 -100.25(16) . . . . ?
O3 C5 C6 O4 -62.1(2) . . . . ?
O6 C8 C9 C10 7.1(3) . . . . ?
O6 C8 C9 C14 -172.13(17) . . . . ?
N1 C1 C2 O1 156.14(14) . . . . ?
N1 C1 C2 C3 34.74(16) . . . . ?
N1 C1 C5 O3 172.06(13) . . . . ?
N1 C1 C5 C6 54.0(2) . . . . ?
C1 N1 C4 C3 2.8(2) . . . . ?
C1 N1 C7 O5 12.1(3) . . . . ?
C1 N1 C7 O6 -168.74(15) . . . . ?
C1 C2 C3 O2 82.83(17) . . . . ?
C1 C2 C3 C4 -34.25(17) . . . . ?
C1 C5 C6 O4 56.8(2) . . . . ?
C2 C1 C5 O3 -73.78(18) . . . . ?
C2 C1 C5 C6 168.14(15) . . . . ?
C2 C3 C4 N1 19.47(18) . . . . ?
C4 N1 C1 C2 -23.42(18) . . . . ?
C4 N1 C1 C5 98.68(17) . . . . ?
C4 N1 C7 O5 170.96(19) . . . . ?
C4 N1 C7 O6 -9.9(2) . . . . ?
C5 C1 C2 O1 34.7(2) . . . . ?
C5 C1 C2 C3 -86.75(17) . . . . ?
C7 O6 C8 C9 175.36(16) . . . . ?
C7 N1 C1 C2 137.46(16) . . . . ?
C7 N1 C1 C5 -100.45(19) . . . . ?
C7 N1 C4 C3 -157.44(17) . . . . ?
C8 O6 C7 O5 -6.7(3) . . . . ?
C8 O6 C7 N1 174.09(16) . . . . ?
C8 C9 C10 C11 -179.6(2) . . . . ?
C8 C9 C14 C13 179.36(19) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C9 0.1(3) . . . . ?
C14 C9 C10 C11 -0.4(3) . . . . ?

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