# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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#  except for the purpose of generating routine backup copies
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data_130718_mdk_2_098

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 N O4'
_chemical_formula_sum            'C19 H21 N O4'
_chemical_formula_weight         327.37

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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                   8.8435(4)
_cell_length_b                   13.8908(7)
_cell_length_c                   14.1790(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1741.80(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4435
_cell_measurement_theta_min      3.1788
_cell_measurement_theta_max      67.3393

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7535
_exptl_absorpt_correction_T_max  0.7881
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11501
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.46
_diffrn_reflns_theta_max         67.45
_reflns_number_total             1796
_reflns_number_gt                1548
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0611P)²+0.2592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_ls_number_reflns         1796
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0601(3) 0.42586(19) -0.09883(16) 0.0808(8) Uani 1 1 d . . .
O2 O 0.2277(3) 0.20125(16) 0.52600(14) 0.0649(6) Uani 1 1 d . . .
O3 O 0.3768(5) 0.0401(2) 0.48938(19) 0.1196(13) Uani 1 1 d . . .
O4 O 0.4378(4) 0.01349(19) 0.34427(17) 0.0948(9) Uani 1 1 d . . .
N1 N 0.0553(3) 0.37177(17) 0.24349(16) 0.0549(6) Uani 1 1 d . . .
C1 C 0.0868(3) 0.3553(2) 0.14932(19) 0.0517(6) Uani 1 1 d . . .
C2 C 0.0438(3) 0.4108(2) 0.0715(2) 0.0570(7) Uani 1 1 d . . .
H2 H -0.0150 0.4659 0.0781 0.068 Uiso 1 1 calc R . .
C3 C 0.0932(4) 0.3794(2) -0.0159(2) 0.0621(8) Uani 1 1 d . . .
C4 C 0.1822(4) 0.2975(3) -0.0262(2) 0.0699(9) Uani 1 1 d . . .
H4 H 0.2147 0.2791 -0.0859 0.084 Uiso 1 1 calc R . .
C5 C 0.2227(4) 0.2436(2) 0.0514(2) 0.0624(8) Uani 1 1 d . . .
H5 H 0.2808 0.1882 0.0441 0.075 Uiso 1 1 calc R . .
C6 C 0.1760(3) 0.2725(2) 0.14040(19) 0.0505(6) Uani 1 1 d . . .
C7 C 0.2020(3) 0.23776(19) 0.23520(19) 0.0489(6) Uani 1 1 d . . .
C8 C 0.1265(3) 0.3017(2) 0.2963(2) 0.0498(7) Uani 1 1 d . . .
C9 C 0.1307(3) 0.2911(2) 0.3938(2) 0.0567(7) Uani 1 1 d . . .
H9 H 0.0808 0.3343 0.4331 0.068 Uiso 1 1 calc R . .
C10 C 0.2110(3) 0.2147(2) 0.4306(2) 0.0527(7) Uani 1 1 d . . .
C11 C 0.2843(3) 0.14696(19) 0.37136(19) 0.0483(6) Uani 1 1 d . . .
C12 C 0.2794(3) 0.1606(2) 0.2738(2) 0.0503(6) Uani 1 1 d . . .
H12 H 0.3286 0.1173 0.2343 0.060 Uiso 1 1 calc R . .
C13 C -0.0087(6) 0.5175(3) -0.0932(3) 0.0942(14) Uani 1 1 d . . .
H13A H 0.0519 0.5590 -0.0544 0.141 Uiso 1 1 calc R . .
H13B H -0.1076 0.5112 -0.0660 0.141 Uiso 1 1 calc R . .
H13C H -0.0171 0.5445 -0.1553 0.141 Uiso 1 1 calc R . .
C14 C -0.0244(4) 0.4551(2) 0.2821(2) 0.0640(8) Uani 1 1 d . . .
H14A H -0.0731 0.4366 0.3406 0.077 Uiso 1 1 calc R . .
H14B H -0.1028 0.4745 0.2382 0.077 Uiso 1 1 calc R . .
C15 C 0.0762(5) 0.5380(3) 0.3002(4) 0.1082(16) Uani 1 1 d . . .
H15A H 0.1567 0.5185 0.3415 0.162 Uiso 1 1 calc R . .
H15B H 0.0194 0.5889 0.3292 0.162 Uiso 1 1 calc R . .
H15C H 0.1180 0.5603 0.2417 0.162 Uiso 1 1 calc R . .
C16 C 0.3660(3) 0.0635(2) 0.4095(2) 0.0548(7) Uani 1 1 d . . .
C17 C 0.5283(6) -0.0674(3) 0.3749(3) 0.0947(14) Uani 1 1 d . . .
H17A H 0.5928 -0.0477 0.4259 0.142 Uiso 1 1 calc R . .
H17B H 0.5891 -0.0899 0.3233 0.142 Uiso 1 1 calc R . .
H17C H 0.4631 -0.1183 0.3960 0.142 Uiso 1 1 calc R . .
C18 C 0.1626(4) 0.2714(3) 0.5872(2) 0.0727(10) Uani 1 1 d . . .
H18A H 0.0539 0.2733 0.5782 0.087 Uiso 1 1 calc R . .
H18B H 0.2031 0.3345 0.5726 0.087 Uiso 1 1 calc R . .
C19 C 0.1976(5) 0.2463(3) 0.6874(2) 0.0831(11) Uani 1 1 d . . .
H19A H 0.1505 0.2923 0.7286 0.125 Uiso 1 1 calc R . .
H19B H 0.3051 0.2475 0.6968 0.125 Uiso 1 1 calc R . .
H19C H 0.1597 0.1831 0.7011 0.125 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.373(4) . ?
O1 C13 1.413(5) . ?
O2 C10 1.373(3) . ?
O2 C18 1.426(4) . ?
O3 C16 1.182(4) . ?
O4 C16 1.320(4) . ?
O4 C17 1.447(4) . ?
N1 C8 1.380(3) . ?
N1 C1 1.383(4) . ?
N1 C14 1.462(4) . ?
C1 C2 1.399(4) . ?
C1 C6 1.400(4) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(5) . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.447(4) . ?
C7 C12 1.384(4) . ?
C7 C8 1.409(4) . ?
C8 C9 1.391(4) . ?
C9 C10 1.380(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.418(4) . ?
C11 C12 1.397(4) . ?
C11 C16 1.470(4) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.477(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.494(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C3 O1 C13 117.8(3) . . ?
C10 O2 C18 117.6(2) . . ?
C16 O4 C17 117.7(3) . . ?
C8 N1 C1 108.4(2) . . ?
C8 N1 C14 125.1(2) . . ?
C1 N1 C14 126.1(2) . . ?
N1 C1 C2 128.0(3) . . ?
N1 C1 C6 109.7(2) . . ?
C2 C1 C6 122.3(3) . . ?
C3 C2 C1 116.5(3) . . ?
C3 C2 H2 121.7 . . ?
C1 C2 H2 121.7 . . ?
O1 C3 C2 123.5(3) . . ?
O1 C3 C4 114.5(3) . . ?
C2 C3 C4 122.0(3) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 134.5(3) . . ?
C1 C6 C7 106.2(2) . . ?
C12 C7 C8 118.7(3) . . ?
C12 C7 C6 134.7(3) . . ?
C8 C7 C6 106.6(2) . . ?
N1 C8 C9 128.8(3) . . ?
N1 C8 C7 109.1(2) . . ?
C9 C8 C7 122.1(3) . . ?
C10 C9 C8 118.1(3) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
O2 C10 C9 122.2(3) . . ?
O2 C10 C11 116.4(3) . . ?
C9 C10 C11 121.4(3) . . ?
C12 C11 C10 118.9(3) . . ?
C12 C11 C16 119.1(2) . . ?
C10 C11 C16 122.0(2) . . ?
C7 C12 C11 120.7(3) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 113.1(3) . . ?
N1 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N1 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 O4 119.3(3) . . ?
O3 C16 C11 127.5(3) . . ?
O4 C16 C11 113.2(2) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 C19 109.6(3) . . ?
O2 C18 H18A 109.7 . . ?
C19 C18 H18A 109.7 . . ?
O2 C18 H18B 109.7 . . ?
C19 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        67.45
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.033
_database_code_depnum_ccdc_archive 'CCDC 988874'
