# 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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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_yyx

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.13 H2.40 N0.27 O0.40'
_chemical_formula_weight         38.18

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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2955(13)
_cell_length_b                   9.3559(19)
_cell_length_c                   12.975(3)
_cell_angle_alpha                80.69(3)
_cell_angle_beta                 89.50(3)
_cell_angle_gamma                75.05(3)
_cell_volume                     728.2(3)
_cell_formula_units_Z            15
_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    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.091
_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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5155
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         29.19
_reflns_number_total             3324
_reflns_number_gt                2135
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0472P)²+0.1154P] 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       0.027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3324
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.1050(2) 0.26138(16) 0.33484(10) 0.0580(4) Uani 1 1 d . . .
N22 N 0.4709(2) 0.17995(16) 0.38536(11) 0.0418(4) Uani 1 1 d . . .
O13 O 0.5255(2) 0.43791(17) 0.73888(10) 0.0628(4) Uani 1 1 d . . .
C4 C 0.2941(3) 0.1961(2) 0.32160(13) 0.0418(4) Uani 1 1 d . . .
C5 C 0.2852(3) 0.3194(2) 0.52016(14) 0.0461(5) Uani 1 1 d . . .
H5 H 0.1487 0.3227 0.4917 0.055 Uiso 1 1 calc R . .
C6 C 0.4748(3) 0.24969(19) 0.47456(13) 0.0404(4) Uani 1 1 d . . .
C7 C 0.4976(3) 0.3799(2) 0.65147(14) 0.0478(5) Uani 1 1 d . . .
C8 C 0.2001(3) 0.0377(2) 0.19997(14) 0.0472(5) Uani 1 1 d . . .
H8A H 0.1645 -0.0221 0.2627 0.057 Uiso 1 1 calc R . .
H8B H 0.0666 0.1129 0.1734 0.057 Uiso 1 1 calc R . .
C9 C 0.6733(3) 0.0881(2) 0.34851(17) 0.0499(5) Uani 1 1 d . . .
C10 C 0.6763(3) 0.2483(2) 0.51794(14) 0.0510(5) Uani 1 1 d . . .
H10 H 0.8057 0.2034 0.4878 0.061 Uiso 1 1 calc R . .
C11 C 0.6862(3) 0.3129(2) 0.60515(15) 0.0541(5) Uani 1 1 d . . .
H11 H 0.8224 0.3113 0.6332 0.065 Uiso 1 1 calc R . .
C12 C 0.3713(3) 0.11674(19) 0.22828(13) 0.0421(4) Uani 1 1 d . . .
C14 C 0.3996(4) 0.2341(2) 0.13509(14) 0.0509(5) Uani 1 1 d . . .
C444 C 0.1158(4) -0.1431(2) 0.10054(16) 0.0607(6) Uani 1 1 d . . .
C16 C 0.2967(3) 0.3844(2) 0.60797(14) 0.0495(5) Uani 1 1 d . . .
H16 H 0.1679 0.4313 0.6377 0.059 Uiso 1 1 calc R . .
C17 C 0.2785(3) -0.0635(2) 0.11841(16) 0.0544(5) Uani 1 1 d . . .
H17A H 0.3029 -0.0033 0.0534 0.065 Uiso 1 1 calc R . .
H17B H 0.4168 -0.1352 0.1425 0.065 Uiso 1 1 calc R . .
C18 C 0.5903(3) 0.0109(2) 0.26912(17) 0.0504(5) Uani 1 1 d . . .
C20 C 0.3379(4) 0.4838(3) 0.79824(17) 0.0678(6) Uani 1 1 d . . .
H20A H 0.2352 0.5682 0.7582 0.102 Uiso 1 1 calc R . .
H20B H 0.3812 0.5116 0.8613 0.102 Uiso 1 1 calc R . .
H20C H 0.2698 0.4026 0.8155 0.102 Uiso 1 1 calc R . .
O12 O 0.5698(3) 0.21628(18) 0.09097(13) 0.0849(6) Uani 1 1 d . . .
C333 C 0.2133(4) 0.3677(2) 0.10140(17) 0.0709(7) Uani 1 1 d . . .
H33A H 0.2511 0.4266 0.0398 0.106 Uiso 1 1 calc R . .
H33B H 0.1830 0.4271 0.1562 0.106 Uiso 1 1 calc R . .
H33C H 0.0852 0.3359 0.0864 0.106 Uiso 1 1 calc R . .
H21 H 0.752(3) 0.014(2) 0.4094(15) 0.059(6) Uiso 1 1 d . . .
H23 H 0.568(3) -0.085(2) 0.3076(15) 0.059(6) Uiso 1 1 d . . .
H22 H 0.767(3) 0.155(2) 0.3158(15) 0.060(6) Uiso 1 1 d . . .
H24 H 0.692(3) -0.010(2) 0.2134(15) 0.060(6) Uiso 1 1 d . . .
N33 N -0.0173(4) -0.2012(2) 0.08945(17) 0.0850(7) 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
O11 C4 1.214(2) . ?
N22 C4 1.355(2) . ?
N22 C6 1.421(2) . ?
N22 C9 1.466(2) . ?
O13 C7 1.365(2) . ?
O13 C20 1.415(2) . ?
C4 C12 1.532(2) . ?
C5 C6 1.382(2) . ?
C5 C16 1.386(3) . ?
C6 C10 1.389(3) . ?
C7 C11 1.375(3) . ?
C7 C16 1.377(3) . ?
C8 C17 1.528(3) . ?
C8 C12 1.533(2) . ?
C9 C18 1.517(3) . ?
C10 C11 1.375(3) . ?
C12 C18 1.516(3) . ?
C12 C14 1.538(3) . ?
C14 O12 1.197(2) . ?
C14 C333 1.485(3) . ?
C444 N33 1.132(3) . ?
C444 C17 1.452(3) . ?

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
C4 N22 C6 126.45(15) . . ?
C4 N22 C9 112.42(15) . . ?
C6 N22 C9 120.99(16) . . ?
C7 O13 C20 117.38(17) . . ?
O11 C4 N22 126.67(16) . . ?
O11 C4 C12 124.84(17) . . ?
N22 C4 C12 108.50(15) . . ?
C6 C5 C16 120.61(18) . . ?
C5 C6 C10 118.41(17) . . ?
C5 C6 N22 122.54(17) . . ?
C10 C6 N22 119.05(16) . . ?
O13 C7 C11 116.32(18) . . ?
O13 C7 C16 124.71(18) . . ?
C11 C7 C16 118.97(17) . . ?
C17 C8 C12 113.05(15) . . ?
N22 C9 C18 103.41(16) . . ?
C11 C10 C6 120.57(18) . . ?
C7 C11 C10 120.94(19) . . ?
C18 C12 C4 102.26(15) . . ?
C18 C12 C8 114.13(15) . . ?
C4 C12 C8 109.43(14) . . ?
C18 C12 C14 111.73(16) . . ?
C4 C12 C14 108.88(14) . . ?
C8 C12 C14 110.05(15) . . ?
O12 C14 C333 121.22(19) . . ?
O12 C14 C12 119.79(19) . . ?
C333 C14 C12 118.99(17) . . ?
N33 C444 C17 176.8(2) . . ?
C7 C16 C5 120.47(18) . . ?
C444 C17 C8 110.36(16) . . ?
C12 C18 C9 104.76(16) . . ?

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 N22 C4 O11 -7.3(3) . . . . ?
C9 N22 C4 O11 177.12(18) . . . . ?
C6 N22 C4 C12 172.93(14) . . . . ?
C9 N22 C4 C12 -2.6(2) . . . . ?
C16 C5 C6 C10 -0.9(3) . . . . ?
C16 C5 C6 N22 179.17(15) . . . . ?
C4 N22 C6 C5 14.0(3) . . . . ?
C9 N22 C6 C5 -170.77(16) . . . . ?
C4 N22 C6 C10 -165.93(16) . . . . ?
C9 N22 C6 C10 9.3(2) . . . . ?
C20 O13 C7 C11 -169.28(17) . . . . ?
C20 O13 C7 C16 10.7(3) . . . . ?
C4 N22 C9 C18 -15.7(2) . . . . ?
C6 N22 C9 C18 168.48(15) . . . . ?
C5 C6 C10 C11 1.0(3) . . . . ?
N22 C6 C10 C11 -179.08(16) . . . . ?
O13 C7 C11 C10 178.67(16) . . . . ?
C16 C7 C11 C10 -1.3(3) . . . . ?
C6 C10 C11 C7 0.1(3) . . . . ?
O11 C4 C12 C18 -160.02(18) . . . . ?
N22 C4 C12 C18 19.73(18) . . . . ?
O11 C4 C12 C8 -38.7(2) . . . . ?
N22 C4 C12 C8 141.08(15) . . . . ?
O11 C4 C12 C14 81.6(2) . . . . ?
N22 C4 C12 C14 -98.61(18) . . . . ?
C17 C8 C12 C18 -57.6(2) . . . . ?
C17 C8 C12 C4 -171.45(16) . . . . ?
C17 C8 C12 C14 69.0(2) . . . . ?
C18 C12 C14 O12 14.7(2) . . . . ?
C4 C12 C14 O12 126.9(2) . . . . ?
C8 C12 C14 O12 -113.1(2) . . . . ?
C18 C12 C14 C333 -165.48(17) . . . . ?
C4 C12 C14 C333 -53.3(2) . . . . ?
C8 C12 C14 C333 66.7(2) . . . . ?
O13 C7 C16 C5 -178.59(17) . . . . ?
C11 C7 C16 C5 1.4(3) . . . . ?
C6 C5 C16 C7 -0.3(3) . . . . ?
N33 C444 C17 C8 7(5) . . . . ?
C12 C8 C17 C444 175.94(17) . . . . ?
C4 C12 C18 C9 -28.47(18) . . . . ?
C8 C12 C18 C9 -146.52(15) . . . . ?
C14 C12 C18 C9 87.83(19) . . . . ?
N22 C9 C18 C12 27.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.842
_diffrn_reflns_theta_full        29.19
_diffrn_measured_fraction_theta_full 0.842
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 1001190'
