# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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
#  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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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_2_ep_114_0ma

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.35

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   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   14.9390(16)
_cell_length_b                   9.9164(11)
_cell_length_c                   19.963(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2957.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7689
_cell_measurement_theta_min      4.43
_cell_measurement_theta_max      67.33

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8332
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13052
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         5.33
_diffrn_reflns_theta_max         67.62
_reflns_number_total             2630
_reflns_number_gt                2468
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0580P)²+0.9670P] 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       0.00077(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2630
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1 O 0.49561(7) -0.34631(10) 0.57117(6) 0.0465(3) Uani 1 1 d . . .
O2 O 0.62261(8) -0.35931(11) 0.62432(7) 0.0597(4) Uani 1 1 d . . .
O3 O 0.69082(7) -0.12998(12) 0.68129(6) 0.0523(3) Uani 1 1 d . . .
N1 N 0.60391(7) 0.05670(11) 0.67973(6) 0.0328(3) Uani 1 1 d . . .
N2 N 0.52129(8) 0.25800(12) 0.67712(6) 0.0395(3) Uani 1 1 d . . .
C1 C 0.31124(11) -0.27637(18) 0.46035(8) 0.0501(4) Uani 1 1 d . . .
H1 H 0.2748 -0.3227 0.4304 0.060 Uiso 1 1 calc R . .
C2 C 0.37495(11) -0.34466(17) 0.49651(8) 0.0469(4) Uani 1 1 d . . .
H2 H 0.3823 -0.4371 0.4910 0.056 Uiso 1 1 calc R . .
C3 C 0.42823(9) -0.27390(14) 0.54140(7) 0.0380(3) Uani 1 1 d . . .
C4 C 0.56407(10) -0.28405(14) 0.60664(8) 0.0396(3) Uani 1 1 d . . .
C5 C 0.55372(9) -0.14173(13) 0.62077(7) 0.0329(3) Uani 1 1 d . . .
C6 C 0.62050(9) -0.07927(14) 0.66214(7) 0.0348(3) Uani 1 1 d . . .
C7 C 0.67544(10) 0.12480(15) 0.71781(8) 0.0413(4) Uani 1 1 d . . .
H7A H 0.7168 0.1681 0.6872 0.050 Uiso 1 1 calc R . .
H7B H 0.7085 0.0591 0.7440 0.050 Uiso 1 1 calc R . .
C8 C 0.63446(11) 0.22852(17) 0.76348(8) 0.0505(4) Uani 1 1 d . . .
H8A H 0.5948 0.1849 0.7953 0.061 Uiso 1 1 calc R . .
H8B H 0.6811 0.2747 0.7883 0.061 Uiso 1 1 calc R . .
C9 C 0.47627(9) -0.07036(13) 0.60219(6) 0.0312(3) Uani 1 1 d . . .
C10 C 0.41637(9) -0.13708(14) 0.55405(7) 0.0346(3) Uani 1 1 d . . .
C11 C 0.35297(10) -0.07008(16) 0.51459(8) 0.0425(4) Uani 1 1 d . . .
H11 H 0.3456 0.0225 0.5196 0.051 Uiso 1 1 calc R . .
C12 C 0.30117(11) -0.13795(17) 0.46857(8) 0.0477(4) Uani 1 1 d . . .
H12 H 0.2594 -0.0912 0.4430 0.057 Uiso 1 1 calc R . .
C13 C 0.45758(9) 0.05742(13) 0.62912(7) 0.0327(3) Uani 1 1 d . . .
C14 C 0.36192(9) 0.10572(15) 0.64113(8) 0.0404(3) Uani 1 1 d . . .
H14A H 0.3221 0.0337 0.6272 0.048 Uiso 1 1 calc R . .
H14B H 0.3544 0.1163 0.6891 0.048 Uiso 1 1 calc R . .
C15 C 0.32908(11) 0.23470(16) 0.60821(9) 0.0486(4) Uani 1 1 d . . .
H15A H 0.3431 0.2325 0.5608 0.058 Uiso 1 1 calc R . .
H15B H 0.2646 0.2410 0.6129 0.058 Uiso 1 1 calc R . .
C16 C 0.37267(12) 0.35728(16) 0.64008(9) 0.0513(4) Uani 1 1 d . . .
H16A H 0.3502 0.4387 0.6190 0.062 Uiso 1 1 calc R . .
H16B H 0.3576 0.3607 0.6873 0.062 Uiso 1 1 calc R . .
C17 C 0.47252(11) 0.35041(15) 0.63211(9) 0.0476(4) Uani 1 1 d . . .
H17A H 0.4854 0.3243 0.5863 0.057 Uiso 1 1 calc R . .
H17B H 0.4964 0.4404 0.6385 0.057 Uiso 1 1 calc R . .
C18 C 0.58338(11) 0.32704(16) 0.72237(9) 0.0489(4) Uani 1 1 d . . .
H18A H 0.5501 0.3869 0.7516 0.059 Uiso 1 1 calc R . .
H18B H 0.6247 0.3813 0.6964 0.059 Uiso 1 1 calc R . .
C19 C 0.52776(9) 0.12473(13) 0.66218(6) 0.0318(3) 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
O1 C3 1.3718(18) . ?
O1 C4 1.3887(18) . ?
O2 C4 1.2027(18) . ?
O3 C6 1.2257(17) . ?
N1 C19 1.3682(17) . ?
N1 C6 1.4152(18) . ?
N1 C7 1.4751(17) . ?
N2 C19 1.3583(18) . ?
N2 C18 1.4646(19) . ?
N2 C17 1.476(2) . ?
C1 C2 1.373(2) . ?
C1 C12 1.391(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(2) . ?
C2 H2 0.9300 . ?
C3 C10 1.391(2) . ?
C4 C5 1.4475(19) . ?
C5 C9 1.4062(19) . ?
C5 C6 1.436(2) . ?
C7 C8 1.505(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C18 1.487(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C13 1.4044(19) . ?
C9 C10 1.4704(19) . ?
C10 C11 1.400(2) . ?
C11 C12 1.377(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C19 1.4071(19) . ?
C13 C14 1.5262(19) . ?
C14 C15 1.519(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.519(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.502(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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 C4 121.91(11) . . ?
C19 N1 C6 123.49(11) . . ?
C19 N1 C7 120.58(12) . . ?
C6 N1 C7 115.92(11) . . ?
C19 N2 C18 123.04(12) . . ?
C19 N2 C17 120.37(12) . . ?
C18 N2 C17 113.45(12) . . ?
C2 C1 C12 119.99(15) . . ?
C2 C1 H1 120.0 . . ?
C12 C1 H1 120.0 . . ?
C1 C2 C3 119.16(15) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
O1 C3 C2 115.82(13) . . ?
O1 C3 C10 121.68(13) . . ?
C2 C3 C10 122.46(14) . . ?
O2 C4 O1 114.16(13) . . ?
O2 C4 C5 128.72(14) . . ?
O1 C4 C5 117.01(12) . . ?
C9 C5 C6 120.43(12) . . ?
C9 C5 C4 121.81(13) . . ?
C6 C5 C4 117.29(12) . . ?
O3 C6 N1 117.62(13) . . ?
O3 C6 C5 126.72(13) . . ?
N1 C6 C5 115.60(12) . . ?
N1 C7 C8 109.29(12) . . ?
N1 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N1 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C18 C8 C7 108.89(13) . . ?
C18 C8 H8A 109.9 . . ?
C7 C8 H8A 109.9 . . ?
C18 C8 H8B 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C13 C9 C5 121.11(12) . . ?
C13 C9 C10 122.36(12) . . ?
C5 C9 C10 116.53(12) . . ?
C3 C10 C11 116.55(13) . . ?
C3 C10 C9 118.68(13) . . ?
C11 C10 C9 124.48(13) . . ?
C12 C11 C10 121.59(15) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C1 120.02(15) . . ?
C11 C12 H12 120.0 . . ?
C1 C12 H12 120.0 . . ?
C9 C13 C19 117.35(12) . . ?
C9 C13 C14 121.96(12) . . ?
C19 C13 C14 118.36(12) . . ?
C15 C14 C13 119.91(13) . . ?
C15 C14 H14A 107.3 . . ?
C13 C14 H14A 107.3 . . ?
C15 C14 H14B 107.3 . . ?
C13 C14 H14B 107.3 . . ?
H14A C14 H14B 106.9 . . ?
C16 C15 C14 110.74(13) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 110.20(13) . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N2 C17 C16 117.00(14) . . ?
N2 C17 H17A 108.0 . . ?
C16 C17 H17A 108.0 . . ?
N2 C17 H17B 108.0 . . ?
C16 C17 H17B 108.0 . . ?
H17A C17 H17B 107.3 . . ?
N2 C18 C8 111.00(13) . . ?
N2 C18 H18A 109.4 . . ?
C8 C18 H18A 109.4 . . ?
N2 C18 H18B 109.4 . . ?
C8 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
N2 C19 N1 118.86(12) . . ?
N2 C19 C13 120.77(12) . . ?
N1 C19 C13 120.38(12) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        67.62
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 984996'
