# 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:
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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_e:\130924a\work\mo_130924a_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N3 O3'
_chemical_formula_weight         333.34

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.3707(17)
_cell_length_b                   6.8494(6)
_cell_length_c                   24.489(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.7180(10)
_cell_angle_gamma                90.00
_cell_volume                     3080.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6121
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      31.89

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9774
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13809
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4495
_reflns_number_gt                3693
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0695P)²+0.4601P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4495
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_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
C1 C 0.10722(5) 0.20993(15) 0.83871(4) 0.0141(2) Uani 1 1 d . . .
C2 C 0.17343(5) 0.11634(15) 0.84981(4) 0.0160(2) Uani 1 1 d . . .
H2 H 0.1841 0.0660 0.8853 0.019 Uiso 1 1 calc R . .
C3 C 0.22371(6) 0.09674(16) 0.80894(4) 0.0184(2) Uani 1 1 d . . .
H3 H 0.2689 0.0337 0.8166 0.022 Uiso 1 1 calc R . .
C4 C 0.20796(6) 0.16921(17) 0.75692(4) 0.0199(2) Uani 1 1 d . . .
H4 H 0.2424 0.1544 0.7290 0.024 Uiso 1 1 calc R . .
C5 C 0.14209(6) 0.26333(18) 0.74545(4) 0.0205(2) Uani 1 1 d . . .
H5 H 0.1314 0.3126 0.7098 0.025 Uiso 1 1 calc R . .
C6 C 0.09218(6) 0.28466(17) 0.78633(4) 0.0186(2) Uani 1 1 d . . .
H6 H 0.0475 0.3504 0.7788 0.022 Uiso 1 1 calc R . .
C7 C 0.05340(5) 0.23579(15) 0.88090(4) 0.0134(2) Uani 1 1 d . . .
C8 C 0.00659(5) 0.24906(14) 0.96299(4) 0.01211(19) Uani 1 1 d . . .
C9 C -0.00772(5) 0.24572(14) 1.01810(4) 0.01187(19) Uani 1 1 d . . .
C10 C -0.08006(5) 0.31122(14) 1.03243(4) 0.01263(19) Uani 1 1 d . . .
C11 C -0.12987(5) 0.37529(15) 0.99052(4) 0.01361(19) Uani 1 1 d . . .
C12 C -0.11363(5) 0.36791(15) 0.93241(4) 0.0143(2) Uani 1 1 d . . .
C13 C -0.10510(5) 0.31586(15) 1.08658(4) 0.0154(2) Uani 1 1 d . . .
H13 H -0.0743 0.2699 1.1157 0.019 Uiso 1 1 calc R . .
C14 C -0.17355(5) 0.38613(16) 1.09777(4) 0.0177(2) Uani 1 1 d . . .
H14 H -0.1890 0.3858 1.1344 0.021 Uiso 1 1 calc R . .
C15 C -0.22057(5) 0.45766(16) 1.05656(4) 0.0187(2) Uani 1 1 d . . .
H15 H -0.2667 0.5103 1.0651 0.022 Uiso 1 1 calc R . .
C16 C -0.19862(5) 0.45016(16) 1.00343(4) 0.0174(2) Uani 1 1 d . . .
H16 H -0.2304 0.4963 0.9749 0.021 Uiso 1 1 calc R . .
C17 C 0.05324(5) 0.18291(14) 1.05350(4) 0.01255(19) Uani 1 1 d . . .
C18 C 0.10208(5) 0.14820(16) 1.14410(4) 0.0169(2) Uani 1 1 d . . .
H18A H 0.1449 0.2270 1.1342 0.020 Uiso 1 1 calc R . .
H18B H 0.1153 0.0082 1.1427 0.020 Uiso 1 1 calc R . .
C19 C 0.07745(7) 0.2022(2) 1.20011(5) 0.0276(3) Uani 1 1 d . . .
H19A H 0.0631 0.3400 1.2005 0.041 Uiso 1 1 calc R . .
H19B H 0.1174 0.1810 1.2269 0.041 Uiso 1 1 calc R . .
H19C H 0.0358 0.1208 1.2095 0.041 Uiso 1 1 calc R . .
N1 N 0.06749(4) 0.20209(13) 0.93552(3) 0.01308(18) Uani 1 1 d . . .
H1 H 0.1086 0.1579 0.9502 0.016 Uiso 1 1 calc R . .
N2 N -0.01335(5) 0.29729(13) 0.87130(4) 0.01462(18) Uani 1 1 d . . .
N3 N -0.04242(4) 0.30565(13) 0.92302(3) 0.01324(18) Uani 1 1 d . . .
O1 O -0.15482(4) 0.41034(12) 0.89405(3) 0.02046(18) Uani 1 1 d . . .
O2 O 0.11201(4) 0.12926(11) 1.03620(3) 0.01642(17) Uani 1 1 d . . .
O3 O 0.04039(4) 0.18928(12) 1.10702(3) 0.01664(17) 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
C1 C2 1.3945(14) . ?
C1 C6 1.4009(14) . ?
C1 C7 1.4621(14) . ?
C2 C3 1.3887(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.3895(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3923(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3855(15) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.3111(13) . ?
C7 N1 1.3744(13) . ?
C8 N1 1.3611(13) . ?
C8 N3 1.3663(12) . ?
C8 C9 1.3829(14) . ?
C9 C10 1.4554(13) . ?
C9 C17 1.4604(13) . ?
C10 C13 1.4170(14) . ?
C10 C11 1.4236(13) . ?
C11 C16 1.4078(14) . ?
C11 C12 1.4636(14) . ?
C12 O1 1.2234(12) . ?
C12 N3 1.4014(12) . ?
C13 C14 1.3815(14) . ?
C13 H13 0.9500 . ?
C14 C15 1.3973(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.3747(15) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O2 1.2278(12) . ?
C17 O3 1.3395(12) . ?
C18 O3 1.4582(12) . ?
C18 C19 1.5034(16) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N1 H1 0.8800 . ?
N2 N3 1.3903(12) . ?

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 C1 C6 119.57(9) . . ?
C2 C1 C7 121.49(9) . . ?
C6 C1 C7 118.93(9) . . ?
C3 C2 C1 119.94(9) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.09(10) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.42(10) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.53(10) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.43(10) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N2 C7 N1 112.10(9) . . ?
N2 C7 C1 124.12(9) . . ?
N1 C7 C1 123.77(9) . . ?
N1 C8 N3 104.28(8) . . ?
N1 C8 C9 131.42(9) . . ?
N3 C8 C9 124.29(9) . . ?
C8 C9 C10 115.59(8) . . ?
C8 C9 C17 114.79(8) . . ?
C10 C9 C17 129.59(9) . . ?
C13 C10 C11 116.62(9) . . ?
C13 C10 C9 123.84(9) . . ?
C11 C10 C9 119.54(9) . . ?
C16 C11 C10 120.80(9) . . ?
C16 C11 C12 116.18(9) . . ?
C10 C11 C12 123.02(9) . . ?
O1 C12 N3 120.34(9) . . ?
O1 C12 C11 126.80(9) . . ?
N3 C12 C11 112.86(8) . . ?
C14 C13 C10 121.10(9) . . ?
C14 C13 H13 119.5 . . ?
C10 C13 H13 119.5 . . ?
C13 C14 C15 121.70(10) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C16 C15 C14 118.56(9) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C11 121.11(10) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
O2 C17 O3 122.01(9) . . ?
O2 C17 C9 123.37(9) . . ?
O3 C17 C9 114.62(8) . . ?
O3 C18 C19 105.72(8) . . ?
O3 C18 H18A 110.6 . . ?
C19 C18 H18A 110.6 . . ?
O3 C18 H18B 110.6 . . ?
C19 C18 H18B 110.6 . . ?
H18A C18 H18B 108.7 . . ?
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 . . ?
C8 N1 C7 107.93(8) . . ?
C8 N1 H1 126.0 . . ?
C7 N1 H1 126.0 . . ?
C7 N2 N3 103.46(8) . . ?
C8 N3 N2 112.21(8) . . ?
C8 N3 C12 124.55(9) . . ?
N2 N3 C12 123.23(8) . . ?
C17 O3 C18 116.51(8) . . ?

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
C6 C1 C2 C3 -0.39(16) . . . . ?
C7 C1 C2 C3 -179.10(10) . . . . ?
C1 C2 C3 C4 -0.39(17) . . . . ?
C2 C3 C4 C5 0.55(17) . . . . ?
C3 C4 C5 C6 0.08(18) . . . . ?
C4 C5 C6 C1 -0.87(17) . . . . ?
C2 C1 C6 C5 1.03(17) . . . . ?
C7 C1 C6 C5 179.77(10) . . . . ?
C2 C1 C7 N2 -170.03(10) . . . . ?
C6 C1 C7 N2 11.26(16) . . . . ?
C2 C1 C7 N1 11.36(16) . . . . ?
C6 C1 C7 N1 -167.36(10) . . . . ?
N1 C8 C9 C10 178.79(10) . . . . ?
N3 C8 C9 C10 -1.07(15) . . . . ?
N1 C8 C9 C17 0.78(16) . . . . ?
N3 C8 C9 C17 -179.07(9) . . . . ?
C8 C9 C10 C13 179.16(9) . . . . ?
C17 C9 C10 C13 -3.19(17) . . . . ?
C8 C9 C10 C11 -0.84(14) . . . . ?
C17 C9 C10 C11 176.81(10) . . . . ?
C13 C10 C11 C16 3.75(14) . . . . ?
C9 C10 C11 C16 -176.25(9) . . . . ?
C13 C10 C11 C12 -176.17(9) . . . . ?
C9 C10 C11 C12 3.83(15) . . . . ?
C16 C11 C12 O1 -4.07(16) . . . . ?
C10 C11 C12 O1 175.85(10) . . . . ?
C16 C11 C12 N3 175.51(9) . . . . ?
C10 C11 C12 N3 -4.56(14) . . . . ?
C11 C10 C13 C14 -2.30(15) . . . . ?
C9 C10 C13 C14 177.70(10) . . . . ?
C10 C13 C14 C15 -0.81(17) . . . . ?
C13 C14 C15 C16 2.54(17) . . . . ?
C14 C15 C16 C11 -1.05(16) . . . . ?
C10 C11 C16 C15 -2.15(16) . . . . ?
C12 C11 C16 C15 177.78(10) . . . . ?
C8 C9 C17 O2 -2.82(15) . . . . ?
C10 C9 C17 O2 179.51(10) . . . . ?
C8 C9 C17 O3 176.78(8) . . . . ?
C10 C9 C17 O3 -0.88(15) . . . . ?
N3 C8 N1 C7 1.24(11) . . . . ?
C9 C8 N1 C7 -178.64(11) . . . . ?
N2 C7 N1 C8 -1.47(12) . . . . ?
C1 C7 N1 C8 177.29(9) . . . . ?
N1 C7 N2 N3 0.99(11) . . . . ?
C1 C7 N2 N3 -177.77(9) . . . . ?
N1 C8 N3 N2 -0.69(11) . . . . ?
C9 C8 N3 N2 179.20(9) . . . . ?
N1 C8 N3 C12 -179.85(9) . . . . ?
C9 C8 N3 C12 0.04(16) . . . . ?
C7 N2 N3 C8 -0.17(11) . . . . ?
C7 N2 N3 C12 179.01(9) . . . . ?
O1 C12 N3 C8 -177.71(10) . . . . ?
C11 C12 N3 C8 2.67(14) . . . . ?
O1 C12 N3 N2 3.21(15) . . . . ?
C11 C12 N3 N2 -176.40(9) . . . . ?
O2 C17 O3 C18 6.02(14) . . . . ?
C9 C17 O3 C18 -173.59(8) . . . . ?
C19 C18 O3 C17 169.36(9) . . . . ?

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
N1 H1 O2 0.88 2.12 2.6222(11) 115.9 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.066
_database_code_depnum_ccdc_archive 'CCDC 972885'
