# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_hxh-5-72-3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H24 N2 O4'
_chemical_formula_weight         344.40

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 212121'

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                   8.088(5)
_cell_length_b                   12.766(5)
_cell_length_c                   19.413(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2004.4(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean 10
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12466
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.52
_reflns_number_total             4532
_reflns_number_gt                3254
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0651P)²+0.1084P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.077(4)
_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   -0.6(12)
_refine_ls_number_reflns         4532
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.33392(15) -0.01059(9) 0.00511(7) 0.0633(4) Uani 1 1 d . . .
O21 O 0.85229(17) 0.13886(9) 0.17000(6) 0.0597(4) Uani 1 1 d . . .
O12 O 0.5033(2) -0.09626(11) -0.06735(8) 0.0796(4) Uani 1 1 d . . .
C1 C 0.6325(2) 0.09213(12) 0.05508(9) 0.0491(4) Uani 1 1 d . . .
N1 N 0.57193(18) 0.03309(12) 0.11207(8) 0.0556(4) Uani 1 1 d . . .
C6 C 0.5946(2) 0.05937(13) -0.01180(9) 0.0507(4) Uani 1 1 d . . .
O22 O 0.7798(3) 0.30702(13) 0.15380(10) 0.1258(9) Uani 1 1 d . . .
C2 C 0.7287(3) 0.18097(13) 0.06595(10) 0.0596(5) Uani 1 1 d . . .
C22 C 0.9182(3) 0.14929(15) 0.24097(10) 0.0652(5) Uani 1 1 d . . .
C11 C 0.4750(2) -0.02659(13) -0.02726(9) 0.0505(4) Uani 1 1 d . . .
C5 C 0.6628(3) 0.11331(16) -0.06707(10) 0.0678(5) Uani 1 1 d . . .
H5 H 0.6455 0.0890 -0.1116 0.081 Uiso 1 1 calc R . .
C12 C 0.1881(2) -0.08088(16) -0.00411(13) 0.0739(6) Uani 1 1 d . . .
C7 C 0.6056(3) -0.06903(17) 0.12578(13) 0.0755(6) Uani 1 1 d . . .
H7 H 0.6679 -0.1147 0.0990 0.091 Uiso 1 1 calc R . .
N2 N 0.4778(3) 0.07854(19) 0.16131(10) 0.0912(6) Uani 1 1 d . . .
C21 C 0.7852(3) 0.21752(15) 0.13515(12) 0.0729(6) Uani 1 1 d . . .
C23 C 0.9707(3) 0.03861(17) 0.25662(12) 0.0814(7) Uani 1 1 d . . .
H23A H 1.0559 0.0178 0.2250 0.122 Uiso 1 1 calc R . .
H23B H 0.8775 -0.0074 0.2519 0.122 Uiso 1 1 calc R . .
H23C H 1.0122 0.0349 0.3029 0.122 Uiso 1 1 calc R . .
C4 C 0.7557(3) 0.2022(2) -0.05670(12) 0.0860(7) Uani 1 1 d . . .
H4 H 0.7987 0.2385 -0.0942 0.103 Uiso 1 1 calc R . .
C3 C 0.7848(3) 0.23706(17) 0.00899(13) 0.0829(7) Uani 1 1 d . . .
H3 H 0.8429 0.2991 0.0156 0.100 Uiso 1 1 calc R . .
C8 C 0.5306(4) -0.0907(3) 0.18595(17) 0.1090(11) Uani 1 1 d . . .
H8 H 0.5318 -0.1542 0.2094 0.131 Uiso 1 1 calc R . .
C25 C 1.0679(4) 0.2204(2) 0.23956(17) 0.1173(12) Uani 1 1 d . . .
H25A H 1.1475 0.1934 0.2074 0.176 Uiso 1 1 calc R . .
H25B H 1.1163 0.2233 0.2847 0.176 Uiso 1 1 calc R . .
H25C H 1.0349 0.2894 0.2257 0.176 Uiso 1 1 calc R . .
C13 C 0.2341(4) -0.1901(2) 0.01774(19) 0.1179(11) Uani 1 1 d . . .
H13A H 0.3103 -0.2194 -0.0149 0.177 Uiso 1 1 calc R . .
H13B H 0.1365 -0.2328 0.0197 0.177 Uiso 1 1 calc R . .
H13C H 0.2849 -0.1879 0.0624 0.177 Uiso 1 1 calc R . .
C14 C 0.1307(4) -0.0747(3) -0.07741(18) 0.1352(13) Uani 1 1 d . . .
H14A H 0.2118 -0.1063 -0.1070 0.203 Uiso 1 1 calc R . .
H14B H 0.1159 -0.0026 -0.0901 0.203 Uiso 1 1 calc R . .
H14C H 0.0276 -0.1113 -0.0821 0.203 Uiso 1 1 calc R . .
C9 C 0.4533(4) -0.0019(4) 0.20542(14) 0.1171(12) Uani 1 1 d . . .
H9 H 0.3896 0.0035 0.2452 0.141 Uiso 1 1 calc R . .
C24 C 0.7840(5) 0.1852(3) 0.28879(13) 0.1300(14) Uani 1 1 d . . .
H24A H 0.7531 0.2557 0.2775 0.195 Uiso 1 1 calc R . .
H24B H 0.8233 0.1826 0.3354 0.195 Uiso 1 1 calc R . .
H24C H 0.6896 0.1401 0.2841 0.195 Uiso 1 1 calc R . .
C15 C 0.0667(4) -0.0335(4) 0.0454(3) 0.1653(18) Uani 1 1 d . . .
H15A H 0.1088 -0.0394 0.0915 0.248 Uiso 1 1 calc R . .
H15B H -0.0369 -0.0699 0.0421 0.248 Uiso 1 1 calc R . .
H15C H 0.0506 0.0391 0.0342 0.248 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
O11 C11 1.318(2) . ?
O11 C12 1.493(2) . ?
O21 C21 1.327(2) . ?
O21 C22 1.483(2) . ?
O12 C11 1.204(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.398(2) . ?
C1 N1 1.426(2) . ?
N1 N2 1.353(2) . ?
N1 C7 1.358(3) . ?
C6 C5 1.389(3) . ?
C6 C11 1.494(2) . ?
O22 C21 1.199(2) . ?
C2 C3 1.393(3) . ?
C2 C21 1.494(3) . ?
C22 C24 1.500(4) . ?
C22 C23 1.506(3) . ?
C22 C25 1.514(4) . ?
C5 C4 1.375(3) . ?
C5 H5 0.9300 . ?
C12 C14 1.499(4) . ?
C12 C15 1.501(4) . ?
C12 C13 1.504(4) . ?
C7 C8 1.345(4) . ?
C7 H7 0.9300 . ?
N2 C9 1.351(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C4 C3 1.371(4) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C8 C9 1.349(4) . ?
C8 H8 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C9 H9 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C11 O11 C12 122.24(15) . . ?
C21 O21 C22 123.55(15) . . ?
C2 C1 C6 120.48(15) . . ?
C2 C1 N1 120.36(16) . . ?
C6 C1 N1 119.16(15) . . ?
N2 N1 C7 112.71(18) . . ?
N2 N1 C1 121.00(16) . . ?
C7 N1 C1 126.20(17) . . ?
C5 C6 C1 118.82(16) . . ?
C5 C6 C11 117.80(16) . . ?
C1 C6 C11 123.25(15) . . ?
C1 C2 C3 118.72(18) . . ?
C1 C2 C21 124.20(17) . . ?
C3 C2 C21 116.98(18) . . ?
O21 C22 C24 110.02(19) . . ?
O21 C22 C23 101.79(15) . . ?
C24 C22 C23 111.5(2) . . ?
O21 C22 C25 108.93(18) . . ?
C24 C22 C25 114.0(2) . . ?
C23 C22 C25 109.9(2) . . ?
O12 C11 O11 125.98(17) . . ?
O12 C11 C6 123.31(16) . . ?
O11 C11 C6 110.56(14) . . ?
C4 C5 C6 120.84(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
O11 C12 C14 109.1(2) . . ?
O11 C12 C15 101.41(19) . . ?
C14 C12 C15 112.6(3) . . ?
O11 C12 C13 109.15(18) . . ?
C14 C12 C13 113.1(3) . . ?
C15 C12 C13 110.8(3) . . ?
C8 C7 N1 106.1(3) . . ?
C8 C7 H7 126.9 . . ?
N1 C7 H7 126.9 . . ?
C9 N2 N1 101.8(2) . . ?
O22 C21 O21 125.6(2) . . ?
O22 C21 C2 123.91(19) . . ?
O21 C21 C2 110.33(16) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C3 C4 C5 119.86(19) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C3 C2 121.01(19) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C7 C8 C9 106.2(2) . . ?
C7 C8 H8 126.9 . . ?
C9 C8 H8 126.9 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C9 N2 113.2(2) . . ?
C8 C9 H9 123.4 . . ?
N2 C9 H9 123.4 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.029
_database_code_depnum_ccdc_archive 'CCDC 995322'
