# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NY41
_database_code_depnum_ccdc_archive 'CCDC 1419082'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 N2 O6'
_chemical_formula_sum            'C14 H18 N2 O6'
_chemical_formula_weight         310.30

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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1957(4)
_cell_length_b                   12.0390(9)
_cell_length_c                   12.8927(10)
_cell_angle_alpha                112.826(2)
_cell_angle_beta                 90.743(2)
_cell_angle_gamma                102.195(2)
_cell_volume                     722.48(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2054
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8717
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.723
_diffrn_reflns_theta_max         28.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3824
_reflns_number_gt                3020
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'APEX2 (Bruker, 2005)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3824
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3878(2) 0.82370(11) 0.27076(10) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.2224(3) 0.56801(12) 0.21557(12) 0.0212(3) Uani 1 1 d . . . . .
O1 O 0.59486(19) 0.93266(9) 0.30774(9) 0.0161(2) Uani 1 1 d . . . . .
O2 O 0.3422(2) 1.08151(10) 0.33952(8) 0.0156(2) Uani 1 1 d . . . . .
O3 O 0.0108(2) 0.62711(10) 0.23416(9) 0.0198(3) Uani 1 1 d . . . . .
O4 O 0.3167(2) 0.54661(11) 0.12686(10) 0.0282(3) Uani 1 1 d . . . . .
O5 O 0.2784(2) 0.54262(11) 0.29310(11) 0.0295(3) Uani 1 1 d . . . . .
O6 O 0.1227(2) 0.65115(10) -0.35490(9) 0.0175(2) Uani 1 1 d . . . . .
C1 C 0.2149(3) 0.80508(13) 0.19086(12) 0.0131(3) Uani 1 1 d . . . . .
C2 C 0.5442(3) 1.03291(13) 0.28168(12) 0.0140(3) Uani 1 1 d . . . . .
H2A H 0.7099 1.1002 0.3023 0.017 Uiso 1 1 calc R U . . .
C3 C 0.4615(3) 0.98640(13) 0.15702(12) 0.0137(3) Uani 1 1 d . . . . .
H3A H 0.6028 0.9527 0.1133 0.016 Uiso 1 1 calc R U . . .
H3B H 0.4334 1.0557 0.1384 0.016 Uiso 1 1 calc R U . . .
C4 C 0.2041(3) 0.88462(13) 0.12479(12) 0.0120(3) Uani 1 1 d . . . . .
H4A H 0.0527 0.9252 0.1471 0.014 Uiso 1 1 calc R U . . .
C5 C 0.4068(3) 1.14299(15) 0.46065(12) 0.0191(3) Uani 1 1 d . . . . .
H5A H 0.5618 1.2139 0.4795 0.023 Uiso 1 1 calc R U . . .
H5B H 0.4509 1.0846 0.4911 0.023 Uiso 1 1 calc R U . . .
C6 C 0.1701(3) 1.18792(17) 0.51167(14) 0.0271(4) Uani 1 1 d . . . . .
H6A H 0.2097 1.2300 0.5941 0.041 Uiso 1 1 calc R U . . .
H6B H 0.1285 1.2459 0.4813 0.041 Uiso 1 1 calc R U . . .
H6C H 0.0180 1.1171 0.4929 0.041 Uiso 1 1 calc R U . . .
C7 C -0.0076(3) 0.69083(14) 0.16118(13) 0.0180(3) Uani 1 1 d . . . . .
H7A H -0.1791 0.7152 0.1668 0.022 Uiso 1 1 calc R U . . .
H7B H -0.0039 0.6336 0.0819 0.022 Uiso 1 1 calc R U . . .
C8 C 0.1642(3) 0.80998(13) -0.00263(12) 0.0122(3) Uani 1 1 d . . . . .
C9 C -0.0073(3) 0.83375(13) -0.07185(12) 0.0128(3) Uani 1 1 d . . . . .
H9A H -0.1179 0.8887 -0.0380 0.015 Uiso 1 1 calc R U . . .
C10 C -0.0193(3) 0.77897(13) -0.18851(12) 0.0138(3) Uani 1 1 d . . . . .
H10A H -0.1357 0.7971 -0.2340 0.017 Uiso 1 1 calc R U . . .
C11 C 0.1405(3) 0.69682(13) -0.23934(12) 0.0131(3) Uani 1 1 d . . . . .
C12 C 0.3057(3) 0.66812(13) -0.17225(12) 0.0145(3) Uani 1 1 d . . . . .
H12A H 0.4099 0.6100 -0.2063 0.017 Uiso 1 1 calc R U . . .
C13 C 0.3166(3) 0.72524(13) -0.05512(12) 0.0149(3) Uani 1 1 d . . . . .
H13A H 0.4308 0.7061 -0.0097 0.018 Uiso 1 1 calc R U . . .
C14 C 0.2926(3) 0.57096(15) -0.40911(13) 0.0220(3) Uani 1 1 d . . . . .
H14A H 0.2625 0.5442 -0.4913 0.033 Uiso 1 1 calc R U . . .
H14B H 0.4777 0.6156 -0.3830 0.033 Uiso 1 1 calc R U . . .
H14C H 0.2537 0.4982 -0.3901 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.2769(18) . ?
N1 O1 1.4179(15) . ?
N2 O5 1.2019(17) . ?
N2 O4 1.2057(18) . ?
N2 O3 1.4061(17) . ?
O1 C2 1.4439(17) . ?
O2 C2 1.3935(17) . ?
O2 C5 1.4435(17) . ?
O3 C7 1.4392(18) . ?
O6 C11 1.3675(16) . ?
O6 C14 1.4325(18) . ?
C1 C7 1.511(2) . ?
C1 C4 1.5166(19) . ?
C2 C3 1.5046(19) . ?
C2 H2A 1.0000 . ?
C3 C4 1.5363(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C8 1.5219(18) . ?
C4 H4A 1.0000 . ?
C5 C6 1.504(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.395(2) . ?
C8 C9 1.3990(19) . ?
C9 C10 1.3825(19) . ?
C9 H9A 0.9500 . ?
C10 C11 1.3983(19) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3935(19) . ?
C12 C13 1.3900(19) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
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
C1 N1 O1 118.59(11) . . ?
O5 N2 O4 129.00(15) . . ?
O5 N2 O3 112.50(13) . . ?
O4 N2 O3 118.46(13) . . ?
N1 O1 C2 115.85(10) . . ?
C2 O2 C5 113.98(11) . . ?
N2 O3 C7 113.08(11) . . ?
C11 O6 C14 116.80(11) . . ?
N1 C1 C7 115.24(13) . . ?
N1 C1 C4 127.91(13) . . ?
C7 C1 C4 116.84(12) . . ?
O2 C2 O1 112.10(11) . . ?
O2 C2 C3 107.68(11) . . ?
O1 C2 C3 109.58(11) . . ?
O2 C2 H2A 109.1 . . ?
O1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C2 C3 C4 109.59(11) . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C1 C4 C8 112.73(11) . . ?
C1 C4 C3 108.89(11) . . ?
C8 C4 C3 109.97(11) . . ?
C1 C4 H4A 108.4 . . ?
C8 C4 H4A 108.4 . . ?
C3 C4 H4A 108.4 . . ?
O2 C5 C6 108.10(12) . . ?
O2 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
O2 C5 H5B 110.1 . . ?
C6 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 C1 112.37(12) . . ?
O3 C7 H7A 109.1 . . ?
C1 C7 H7A 109.1 . . ?
O3 C7 H7B 109.1 . . ?
C1 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C13 C8 C9 117.80(13) . . ?
C13 C8 C4 121.16(12) . . ?
C9 C8 C4 120.71(12) . . ?
C10 C9 C8 121.46(13) . . ?
C10 C9 H9A 119.3 . . ?
C8 C9 H9A 119.3 . . ?
C9 C10 C11 119.76(13) . . ?
C9 C10 H10A 120.1 . . ?
C11 C10 H10A 120.1 . . ?
O6 C11 C12 124.63(13) . . ?
O6 C11 C10 115.53(12) . . ?
C12 C11 C10 119.83(13) . . ?
C13 C12 C11 119.41(13) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C8 121.67(13) . . ?
C12 C13 H13A 119.2 . . ?
C8 C13 H13A 119.2 . . ?
O6 C14 H14A 109.5 . . ?
O6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O6 C14 H14C 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 O1 C2 21.16(17) . . . . ?
O5 N2 O3 C7 162.34(12) . . . . ?
O4 N2 O3 C7 -19.65(18) . . . . ?
O1 N1 C1 C7 -176.58(11) . . . . ?
O1 N1 C1 C4 2.1(2) . . . . ?
C5 O2 C2 O1 66.25(15) . . . . ?
C5 O2 C2 C3 -173.15(11) . . . . ?
N1 O1 C2 O2 66.24(14) . . . . ?
N1 O1 C2 C3 -53.25(15) . . . . ?
O2 C2 C3 C4 -60.57(14) . . . . ?
O1 C2 C3 C4 61.61(14) . . . . ?
N1 C1 C4 C8 130.29(15) . . . . ?
C7 C1 C4 C8 -51.03(16) . . . . ?
N1 C1 C4 C3 8.0(2) . . . . ?
C7 C1 C4 C3 -173.35(12) . . . . ?
C2 C3 C4 C1 -38.52(15) . . . . ?
C2 C3 C4 C8 -162.49(11) . . . . ?
C2 O2 C5 C6 -178.77(12) . . . . ?
N2 O3 C7 C1 -70.50(15) . . . . ?
N1 C1 C7 O3 3.14(19) . . . . ?
C4 C1 C7 O3 -175.71(11) . . . . ?
C1 C4 C8 C13 -48.00(17) . . . . ?
C3 C4 C8 C13 73.72(16) . . . . ?
C1 C4 C8 C9 138.73(13) . . . . ?
C3 C4 C8 C9 -99.56(15) . . . . ?
C13 C8 C9 C10 -2.4(2) . . . . ?
C4 C8 C9 C10 171.14(12) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C14 O6 C11 C12 -1.8(2) . . . . ?
C14 O6 C11 C10 177.38(12) . . . . ?
C9 C10 C11 O6 -177.49(12) . . . . ?
C9 C10 C11 C12 1.7(2) . . . . ?
O6 C11 C12 C13 176.77(12) . . . . ?
C10 C11 C12 C13 -2.3(2) . . . . ?
C11 C12 C13 C8 0.6(2) . . . . ?
C9 C8 C13 C12 1.7(2) . . . . ?
C4 C8 C13 C12 -171.78(13) . . . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6

