# 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 N O3'
_chemical_formula_weight         207.22

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.1081(9)
_cell_length_b                   9.6334(3)
_cell_length_c                   8.0059(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1010.95(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3480
_cell_measurement_theta_min      6.80
_cell_measurement_theta_max      68.10

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.824
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5343
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.755
_diffrn_reflns_theta_max         68.143
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 0.874
_reflns_number_total             1608
_reflns_number_gt                1372
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_max     0.751
_reflns_Friedel_fraction_full    0.753

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0336P)²+0.1447P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 493 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1608
_refine_ls_number_parameters     140
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0788
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.034
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.17620(12) 0.26409(16) 0.8567(2) 0.0389(4) Uani 1 1 d . . . . .
O2 O 0.25637(16) 0.00375(19) 1.1280(3) 0.0560(6) Uani 1 1 d . . . . .
O3 O 0.06743(16) -0.0103(2) 0.8445(3) 0.0625(6) Uani 1 1 d D . . . .
H3O H 0.122(2) -0.014(4) 0.797(4) 0.075 Uiso 1 1 d D U . . .
N1 N 0.16786(15) 0.1617(2) 0.9820(3) 0.0386(5) Uani 1 1 d . . . . .
C1 C 0.1214(2) 0.6648(3) 1.0234(5) 0.0573(8) Uani 1 1 d . . . . .
H1 H 0.1106 0.7550 1.0605 0.069 Uiso 1 1 calc R U . . .
C2 C 0.2013(2) 0.6359(3) 0.9174(5) 0.0541(8) Uani 1 1 d . . . . .
H2 H 0.2436 0.7071 0.8804 0.065 Uiso 1 1 calc R U . . .
C3 C 0.2186(2) 0.5009(3) 0.8661(4) 0.0458(7) Uani 1 1 d . . . . .
H3 H 0.2730 0.4805 0.7958 0.055 Uiso 1 1 calc R U . . .
C4 C 0.15441(18) 0.3972(2) 0.9202(3) 0.0371(6) Uani 1 1 d . . . . .
C5 C 0.25799(19) 0.1060(3) 1.0371(4) 0.0406(6) Uani 1 1 d . . . . .
C6 C 0.3533(2) 0.1782(3) 0.9841(4) 0.0517(8) Uani 1 1 d . . . . .
H6A H 0.4092 0.1469 1.0518 0.078 Uiso 1 1 calc R U . . .
H6B H 0.3450 0.2765 0.9975 0.078 Uiso 1 1 calc R U . . .
H6C H 0.3670 0.1575 0.8690 0.078 Uiso 1 1 calc R U . . .
C7 C 0.0577(2) 0.5592(3) 1.0740(4) 0.0515(8) Uani 1 1 d . . . . .
H7 H 0.0037 0.5804 1.1450 0.062 Uiso 1 1 calc R U . . .
C8 C 0.07071(19) 0.4215(3) 1.0233(3) 0.0398(6) Uani 1 1 d . . . . .
C9 C 0.07191(18) 0.0852(3) 0.9771(4) 0.0409(6) Uani 1 1 d . . . . .
H9 H 0.0644 0.0341 1.0823 0.049 Uiso 1 1 calc R U . . .
C10 C -0.01516(19) 0.1874(3) 0.9627(4) 0.0472(7) Uani 1 1 d . . . . .
H10A H -0.0786 0.1399 0.9878 0.057 Uiso 1 1 calc R U . . .
H10B H -0.0190 0.2204 0.8484 0.057 Uiso 1 1 calc R U . . .
C11 C -0.0041(2) 0.3117(3) 1.0793(4) 0.0496(8) Uani 1 1 d . . . . .
H11A H -0.0705 0.3547 1.0924 0.059 Uiso 1 1 calc R U . . .
H11B H 0.0169 0.2781 1.1882 0.059 Uiso 1 1 calc R U . . .


_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 C4 1.409(3) . ?
O1 N1 1.411(3) . ?
O2 C5 1.225(3) . ?
O3 C9 1.405(4) . ?
O3 H3O 0.81(2) . ?
N1 C5 1.370(3) . ?
N1 C9 1.458(3) . ?
C1 C2 1.375(5) . ?
C1 C7 1.378(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C8 1.393(3) . ?
C5 C6 1.491(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.397(4) . ?
C7 H7 0.9300 . ?
C8 C11 1.511(4) . ?
C9 C10 1.512(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.525(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 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
C4 O1 N1 111.35(19) . . ?
C9 O3 H3O 110(3) . . ?
C5 N1 O1 115.8(2) . . ?
C5 N1 C9 123.7(2) . . ?
O1 N1 C9 113.6(2) . . ?
C2 C1 C7 119.6(3) . . ?
C2 C1 H1 120.2 . . ?
C7 C1 H1 120.2 . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C8 123.1(2) . . ?
C3 C4 O1 115.1(2) . . ?
C8 C4 O1 121.8(2) . . ?
O2 C5 N1 119.4(2) . . ?
O2 C5 C6 123.9(3) . . ?
N1 C5 C6 116.6(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 C8 122.7(3) . . ?
C1 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C4 C8 C7 115.4(2) . . ?
C4 C8 C11 124.7(2) . . ?
C7 C8 C11 119.9(3) . . ?
O3 C9 N1 112.8(2) . . ?
O3 C9 C10 109.7(2) . . ?
N1 C9 C10 108.91(19) . . ?
O3 C9 H9 108.5 . . ?
N1 C9 H9 108.5 . . ?
C10 C9 H9 108.5 . . ?
C9 C10 C11 113.1(2) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C8 C11 C10 115.5(2) . . ?
C8 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C8 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?

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
O3 H3O O2 0.81(2) 2.10(2) 2.891(3) 165(4) 3_554

_refine_diff_density_max         0.115
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.032

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 1003334'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H17 N O3'
_chemical_formula_weight         211.25

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.9758(10)
_cell_length_b                   6.7000(5)
_cell_length_c                   14.3713(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.070(8)
_cell_angle_gamma                90
_cell_volume                     1083.10(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4417
_cell_measurement_theta_min      6.60
_cell_measurement_theta_max      68.10

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.770
_shelx_estimated_absorpt_T_min   0.791
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5306
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.559
_diffrn_reflns_theta_max         59.966
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.777
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.777
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.777
_reflns_number_total             1519
_reflns_number_gt                1187
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²+3.3000P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1519
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0996
_refine_ls_wR_factor_ref         0.2680
_refine_ls_wR_factor_gt          0.2607
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2344(3) 0.2120(5) 0.0798(2) 0.0396(10) Uani 1 1 d . . . . .
O2 O 0.3116(4) 0.3328(6) -0.0972(3) 0.0597(13) Uani 1 1 d . . . . .
H2 H 0.3512 0.4335 -0.0761 0.072 Uiso 1 1 calc R U . . .
O3 O 0.5169(4) 0.3992(7) 0.1154(3) 0.0702(14) Uani 1 1 d . . . . .
N4 N 0.3471(4) 0.2293(7) 0.0694(3) 0.0414(12) Uani 1 1 d . . . . .
C5 C 0.4262(5) 0.3564(8) 0.1320(4) 0.0457(14) Uani 1 1 d . . . . .
C6 C 0.2257(4) 0.0286(8) 0.1323(4) 0.0415(13) Uani 1 1 d . . . . .
H6 H 0.2981 0.0139 0.1903 0.050 Uiso 1 1 calc R U . . .
C7 C 0.1221(5) 0.0629(9) 0.1666(4) 0.0514(15) Uani 1 1 d . . . . .
H7A H 0.0539 0.1083 0.1116 0.062 Uiso 1 1 calc R U . . .
H7B H 0.1419 0.1649 0.2176 0.062 Uiso 1 1 calc R U . . .
C8 C 0.2777(6) -0.0051(8) -0.0693(4) 0.0529(15) Uani 1 1 d . . . . .
H8A H 0.2993 -0.0564 -0.1239 0.064 Uiso 1 1 calc R U . . .
H8B H 0.1947 0.0340 -0.0955 0.064 Uiso 1 1 calc R U . . .
C9 C 0.2918(6) -0.1726(8) 0.0068(5) 0.0552(16) Uani 1 1 d . . . . .
H9A H 0.2756 -0.2994 -0.0278 0.066 Uiso 1 1 calc R U . . .
H9B H 0.3738 -0.1751 0.0513 0.066 Uiso 1 1 calc R U . . .
C10 C 0.3519(5) 0.1769(8) -0.0278(4) 0.0469(14) Uani 1 1 d . . . . .
H10 H 0.4346 0.1470 -0.0204 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4002(6) 0.4304(9) 0.2200(4) 0.0562(16) Uani 1 1 d . . . . .
H11A H 0.3911 0.3191 0.2588 0.084 Uiso 1 1 calc R U . . .
H11B H 0.3281 0.5072 0.1985 0.084 Uiso 1 1 calc R U . . .
H11C H 0.4647 0.5129 0.2594 0.084 Uiso 1 1 calc R U . . .
C12 C 0.2120(5) -0.1520(8) 0.0673(4) 0.0435(14) Uani 1 1 d . . . . .
C13 C 0.0923(6) -0.1323(10) 0.2077(5) 0.0646(18) Uani 1 1 d . . . . .
H13A H 0.0278 -0.1099 0.2329 0.078 Uiso 1 1 calc R U . . .
H13B H 0.1610 -0.1774 0.2623 0.078 Uiso 1 1 calc R U . . .
C14 C 0.1339(5) -0.2935(9) 0.0673(4) 0.0542(15) Uani 1 1 d . . . . .
H14 H 0.1280 -0.4022 0.0257 0.065 Uiso 1 1 calc R U . . .
C15 C 0.0559(6) -0.2933(10) 0.1275(5) 0.0674(19) Uani 1 1 d . . . . .
H15A H 0.0595 -0.4230 0.1584 0.081 Uiso 1 1 calc R U . . .
H15B H -0.0255 -0.2704 0.0847 0.081 Uiso 1 1 calc R U . . .


_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 N4 1.412(5) . ?
O1 C6 1.464(6) . ?
O2 C10 1.411(7) . ?
O2 H2 0.8200 . ?
O3 C5 1.223(7) . ?
N4 C5 1.359(7) . ?
N4 C10 1.461(7) . ?
C5 C11 1.487(8) . ?
C6 C12 1.502(7) . ?
C6 C7 1.502(7) . ?
C6 H6 0.9800 . ?
C7 C13 1.527(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C10 1.506(8) . ?
C8 C9 1.536(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C12 1.503(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C14 1.332(8) . ?
C13 C15 1.529(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.474(9) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 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
N4 O1 C6 111.3(3) . . ?
C10 O2 H2 109.5 . . ?
C5 N4 O1 117.1(4) . . ?
C5 N4 C10 122.4(4) . . ?
O1 N4 C10 115.7(4) . . ?
O3 C5 N4 118.8(5) . . ?
O3 C5 C11 123.1(5) . . ?
N4 C5 C11 118.0(5) . . ?
O1 C6 C12 111.6(4) . . ?
O1 C6 C7 104.7(4) . . ?
C12 C6 C7 113.6(4) . . ?
O1 C6 H6 108.9 . . ?
C12 C6 H6 108.9 . . ?
C7 C6 H6 108.9 . . ?
C6 C7 C13 109.0(5) . . ?
C6 C7 H7A 109.9 . . ?
C13 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
C13 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C10 C8 C9 113.8(5) . . ?
C10 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C10 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C12 C9 C8 114.1(5) . . ?
C12 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C12 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
O2 C10 N4 112.5(4) . . ?
O2 C10 C8 107.9(4) . . ?
N4 C10 C8 111.2(4) . . ?
O2 C10 H10 108.4 . . ?
N4 C10 H10 108.4 . . ?
C8 C10 H10 108.4 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C6 120.0(5) . . ?
C14 C12 C9 121.4(5) . . ?
C6 C12 C9 118.5(5) . . ?
C7 C13 C15 110.9(5) . . ?
C7 C13 H13A 109.5 . . ?
C15 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C15 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C12 C14 C15 125.9(6) . . ?
C12 C14 H14 117.1 . . ?
C15 C14 H14 117.1 . . ?
C14 C15 C13 111.7(5) . . ?
C14 C15 H15A 109.3 . . ?
C13 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C13 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?

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 O1 N4 C5 -102.3(5) . . . . ?
C6 O1 N4 C10 101.5(5) . . . . ?
O1 N4 C5 O3 -168.6(5) . . . . ?
C10 N4 C5 O3 -14.1(8) . . . . ?
O1 N4 C5 C11 13.8(7) . . . . ?
C10 N4 C5 C11 168.4(5) . . . . ?
N4 O1 C6 C12 -74.8(5) . . . . ?
N4 O1 C6 C7 161.9(4) . . . . ?
O1 C6 C7 C13 170.8(4) . . . . ?
C12 C6 C7 C13 48.9(6) . . . . ?
C10 C8 C9 C12 85.8(6) . . . . ?
C5 N4 C10 O2 -74.4(6) . . . . ?
O1 N4 C10 O2 80.5(5) . . . . ?
C5 N4 C10 C8 164.4(5) . . . . ?
O1 N4 C10 C8 -40.7(6) . . . . ?
C9 C8 C10 O2 -167.1(4) . . . . ?
C9 C8 C10 N4 -43.3(6) . . . . ?
O1 C6 C12 C14 -136.9(5) . . . . ?
C7 C6 C12 C14 -18.8(7) . . . . ?
O1 C6 C12 C9 46.0(6) . . . . ?
C7 C6 C12 C9 164.0(5) . . . . ?
C8 C9 C12 C14 121.1(6) . . . . ?
C8 C9 C12 C6 -61.8(7) . . . . ?
C6 C7 C13 C15 -61.8(7) . . . . ?
C6 C12 C14 C15 -0.3(9) . . . . ?
C9 C12 C14 C15 176.7(6) . . . . ?
C12 C14 C15 C13 -12.2(9) . . . . ?
C7 C13 C15 C14 42.9(8) . . . . ?

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
O2 H2 O3 0.82 2.16 2.807(6) 135.3 3_665

_refine_diff_density_max         0.611
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.098

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 1003335'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 N O4'
_chemical_formula_weight         318.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.7071(2)
_cell_length_b                   4.847
_cell_length_c                   14.6978(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.347(7)
_cell_angle_gamma                90
_cell_volume                     895.67(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10447
_cell_measurement_theta_min      6.60
_cell_measurement_theta_max      68.10

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             342
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.675
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_T_max  0.859
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10812
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         6.576
_diffrn_reflns_theta_max         68.144
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             3101
_reflns_number_gt                2870
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_max     0.908
_reflns_Friedel_fraction_full    0.916

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0949P)²+0.0398P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.52(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3101
_refine_ls_number_parameters     211
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6709(2) 0.9315(5) 0.0658(2) 0.0721(8) Uani 1 1 d . . . . .
O2 O 0.40956(15) 0.3333(4) 0.17133(12) 0.0450(5) Uani 1 1 d . . . . .
O3 O 0.2708(2) -0.0195(5) 0.07731(16) 0.0626(6) Uani 1 1 d . . . . .
O4 O 0.1036(3) -0.1810(6) 0.2439(3) 0.0902(10) Uani 1 1 d . . . . .
N1 N 0.30456(19) 0.4102(5) 0.13525(16) 0.0444(5) Uani 1 1 d . . . . .
C1 C 0.8249(7) 0.6705(16) -0.0189(6) 0.138(3) Uani 1 1 d . . . . .
H1A H 0.7678 0.7522 -0.0600 0.207 Uiso 1 1 calc R U . . .
H1B H 0.8591 0.5320 -0.0510 0.207 Uiso 1 1 calc R U . . .
H1C H 0.8756 0.8103 0.0035 0.207 Uiso 1 1 calc R U . . .
C2 C 0.7819(4) 0.5417(9) 0.0599(3) 0.0735(10) Uani 1 1 d . . . . .
H2A H 0.8402 0.5099 0.1091 0.088 Uiso 1 1 calc R U . . .
H2B H 0.7519 0.3634 0.0406 0.088 Uiso 1 1 calc R U . . .
C3 C 0.6984(2) 0.7087(6) 0.0970(2) 0.0515(7) Uani 1 1 d . . . . .
C4 C 0.6490(2) 0.5816(6) 0.1746(2) 0.0470(6) Uani 1 1 d . . . . .
H4A H 0.7040 0.5530 0.2268 0.056 Uiso 1 1 calc R U . . .
H4B H 0.6199 0.4025 0.1552 0.056 Uiso 1 1 calc R U . . .
C5 C 0.5612(2) 0.7571(7) 0.2049(2) 0.0501(7) Uani 1 1 d . . . . .
H5A H 0.5067 0.7891 0.1526 0.060 Uiso 1 1 calc R U . . .
H5B H 0.5904 0.9348 0.2259 0.060 Uiso 1 1 calc R U . . .
C6 C 0.5112(2) 0.6227(6) 0.28145(19) 0.0438(6) Uani 1 1 d . . . . .
C7 C 0.4350(2) 0.4184(6) 0.26375(18) 0.0396(6) Uani 1 1 d . . . . .
C8 C 0.3871(2) 0.2893(6) 0.33258(18) 0.0424(6) Uani 1 1 d . . . . .
C9 C 0.3016(2) 0.0741(6) 0.3131(2) 0.0456(6) Uani 1 1 d . . . . .
H9A H 0.3164 -0.0775 0.3561 0.055 Uiso 1 1 calc R U . . .
H9B H 0.3008 0.0022 0.2515 0.055 Uiso 1 1 calc R U . . .
C10 C 0.1937(3) 0.1986(7) 0.3220(2) 0.0550(8) Uani 1 1 d . . . . .
H10A H 0.1917 0.2360 0.3866 0.066 Uiso 1 1 calc R U . . .
H10B H 0.1881 0.3744 0.2902 0.066 Uiso 1 1 calc R U . . .
C11 C 0.0985(3) 0.0321(7) 0.2866(2) 0.0536(7) Uani 1 1 d . . . . .
C12 C -0.0062(3) 0.1461(12) 0.3041(5) 0.0919(15) Uani 1 1 d . . . . .
H12A H -0.0035 0.1680 0.3700 0.110 Uiso 1 1 calc R U . . .
H12B H -0.0142 0.3287 0.2770 0.110 Uiso 1 1 calc R U . . .
C13 C -0.1023(4) -0.0148(13) 0.2695(5) 0.1032(18) Uani 1 1 d . . . . .
H13A H -0.1130 -0.0133 0.2035 0.155 Uiso 1 1 calc R U . . .
H13B H -0.1629 0.0657 0.2915 0.155 Uiso 1 1 calc R U . . .
H13C H -0.0934 -0.2015 0.2910 0.155 Uiso 1 1 calc R U . . .
C15 C 0.2455(2) 0.2212(6) 0.08457(18) 0.0469(7) Uani 1 1 d . . . . .
C16 C 0.1401(3) 0.3342(9) 0.0398(3) 0.0712(10) Uani 1 1 d . . . . .
H16A H 0.1316 0.2990 -0.0251 0.107 Uiso 1 1 calc R U . . .
H16B H 0.1378 0.5295 0.0503 0.107 Uiso 1 1 calc R U . . .
H16C H 0.0836 0.2462 0.0658 0.107 Uiso 1 1 calc R U . . .
C18 C 0.4198(3) 0.3790(7) 0.42240(19) 0.0529(7) Uani 1 1 d . . . . .
H18 H 0.3901 0.2986 0.4702 0.063 Uiso 1 1 calc R U . . .
C19 C 0.4943(3) 0.5819(8) 0.4421(2) 0.0581(8) Uani 1 1 d . . . . .
H19 H 0.5140 0.6386 0.5026 0.070 Uiso 1 1 calc R U . . .
C20 C 0.5404(3) 0.7027(7) 0.3727(2) 0.0549(7) Uani 1 1 d . . . . .
H20 H 0.5916 0.8392 0.3870 0.066 Uiso 1 1 calc R U . . .


_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 1.205(4) . ?
O2 N1 1.412(3) . ?
O2 C7 1.411(3) . ?
O3 C15 1.219(4) . ?
O4 C11 1.215(5) . ?
N1 C15 1.340(4) . ?
C1 C2 1.488(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.498(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.512(4) . ?
C4 C5 1.519(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.517(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.383(4) . ?
C6 C20 1.394(4) . ?
C7 C8 1.402(4) . ?
C8 C18 1.395(4) . ?
C8 C9 1.503(4) . ?
C9 C10 1.521(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.484(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.496(5) . ?
C12 C13 1.476(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.507(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 C19 1.366(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
N1 O2 C7 110.87(18) . . ?
C15 N1 O2 116.8(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 114.6(4) . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C3 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
O1 C3 C2 121.9(3) . . ?
O1 C3 C4 121.5(3) . . ?
C2 C3 C4 116.6(3) . . ?
C3 C4 C5 113.3(2) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 C6 112.4(2) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C20 117.5(3) . . ?
C7 C6 C5 121.7(2) . . ?
C20 C6 C5 120.8(3) . . ?
C6 C7 C8 123.3(2) . . ?
C6 C7 O2 116.5(2) . . ?
C8 C7 O2 120.1(2) . . ?
C18 C8 C7 116.3(3) . . ?
C18 C8 C9 120.3(2) . . ?
C7 C8 C9 123.4(2) . . ?
C8 C9 C10 110.1(2) . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 116.9(3) . . ?
C11 C10 H10A 108.1 . . ?
C9 C10 H10A 108.1 . . ?
C11 C10 H10B 108.1 . . ?
C9 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
O4 C11 C10 122.8(3) . . ?
O4 C11 C12 121.2(3) . . ?
C10 C11 C12 116.0(3) . . ?
C13 C12 C11 117.2(4) . . ?
C13 C12 H12A 108.0 . . ?
C11 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C11 C12 H12B 108.0 . . ?
H12A C12 H12B 107.2 . . ?
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 . . ?
O3 C15 N1 124.7(3) . . ?
O3 C15 C16 122.6(3) . . ?
N1 C15 C16 112.6(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C18 C8 121.8(3) . . ?
C19 C18 H18 119.1 . . ?
C8 C18 H18 119.1 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C6 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C6 C20 H20 119.6 . . ?

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
C2 H2B O1 0.97 2.39 3.283(5) 153.7 1_545
C10 H10B O4 0.97 2.46 3.360(5) 154.4 1_565

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 1003336'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22

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   'P 21/c'

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

_cell_length_a                   20.667(3)
_cell_length_b                   5.2935(8)
_cell_length_c                   9.2989(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.551(4)
_cell_angle_gamma                90.00
_cell_volume                     1014.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9863
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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            8734
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.04
_reflns_number_total             1792
_reflns_number_gt                1053
_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)+(0.0391P)²+0.1149P] 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         1792
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.25323(6) 0.3311(2) 0.66737(13) 0.0549(4) Uani 1 1 d . . .
N1 N 0.36107(7) 0.3346(3) 0.74282(15) 0.0529(4) Uani 1 1 d . . .
H1 H 0.3715 0.2618 0.8241 0.063 Uiso 1 1 calc R . .
O2 O 0.39142(7) 0.4128(3) 0.52000(14) 0.0692(5) Uani 1 1 d . . .
C8 C 0.18999(9) 0.4104(4) 0.67931(19) 0.0450(5) Uani 1 1 d . . .
C3 C 0.17463(9) 0.6091(3) 0.76557(19) 0.0474(5) Uani 1 1 d . . .
C9 C 0.30432(8) 0.4894(4) 0.73046(18) 0.0467(5) Uani 1 1 d . . .
H9 H 0.3112 0.6302 0.6650 0.056 Uiso 1 1 calc R . .
C2 C 0.22679(10) 0.7484(4) 0.8534(2) 0.0625(6) Uani 1 1 d . . .
H2A H 0.2119 0.7886 0.9471 0.075 Uiso 1 1 calc R . .
H2B H 0.2360 0.9058 0.8057 0.075 Uiso 1 1 calc R . .
C1 C 0.28811(9) 0.5921(4) 0.87320(19) 0.0540(5) Uani 1 1 d . . .
H1A H 0.3236 0.6960 0.9141 0.065 Uiso 1 1 calc R . .
H1B H 0.2819 0.4540 0.9393 0.065 Uiso 1 1 calc R . .
C7 C 0.14281(10) 0.2745(4) 0.6001(2) 0.0608(6) Uani 1 1 d . . .
H7 H 0.1544 0.1406 0.5427 0.073 Uiso 1 1 calc R . .
C10 C 0.39888(9) 0.2969(4) 0.6343(2) 0.0525(5) Uani 1 1 d . . .
C4 C 0.10916(11) 0.6674(4) 0.7687(2) 0.0682(6) Uani 1 1 d . . .
H4 H 0.0971 0.8007 0.8260 0.082 Uiso 1 1 calc R . .
C6 C 0.07878(10) 0.3370(5) 0.6060(3) 0.0720(7) Uani 1 1 d . . .
H6 H 0.0468 0.2451 0.5529 0.086 Uiso 1 1 calc R . .
C11 C 0.45036(10) 0.1008(4) 0.6619(2) 0.0799(7) Uani 1 1 d . . .
H11A H 0.4362 -0.0550 0.6169 0.120 Uiso 1 1 calc R . .
H11B H 0.4585 0.0753 0.7639 0.120 Uiso 1 1 calc R . .
H11C H 0.4895 0.1560 0.6225 0.120 Uiso 1 1 calc R . .
C5 C 0.06195(11) 0.5347(5) 0.6899(3) 0.0765(7) Uani 1 1 d . . .
H5 H 0.0185 0.5788 0.6934 0.092 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 C8 1.385(2) . ?
O1 C9 1.436(2) . ?
N1 C10 1.339(2) . ?
N1 C9 1.428(2) . ?
N1 H1 0.8600 . ?
O2 C10 1.226(2) . ?
C8 C3 1.375(2) . ?
C8 C7 1.377(3) . ?
C3 C4 1.390(3) . ?
C3 C2 1.494(3) . ?
C9 C1 1.497(2) . ?
C9 H9 0.9800 . ?
C2 C1 1.513(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C7 C6 1.369(3) . ?
C7 H7 0.9300 . ?
C10 C11 1.494(3) . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C6 C5 1.367(3) . ?
C6 H6 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C5 H5 0.9300 . ?

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
C8 O1 C9 117.27(14) . . ?
C10 N1 C9 123.32(15) . . ?
C10 N1 H1 118.3 . . ?
C9 N1 H1 118.3 . . ?
C3 C8 C7 121.67(18) . . ?
C3 C8 O1 122.78(17) . . ?
C7 C8 O1 115.54(17) . . ?
C8 C3 C4 116.87(19) . . ?
C8 C3 C2 120.42(17) . . ?
C4 C3 C2 122.70(19) . . ?
N1 C9 O1 105.72(14) . . ?
N1 C9 C1 112.17(14) . . ?
O1 C9 C1 111.42(14) . . ?
N1 C9 H9 109.1 . . ?
O1 C9 H9 109.1 . . ?
C1 C9 H9 109.1 . . ?
C3 C2 C1 110.97(16) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C9 C1 C2 109.58(15) . . ?
C9 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
C9 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
C6 C7 C8 119.9(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
O2 C10 N1 122.55(19) . . ?
O2 C10 C11 122.34(18) . . ?
N1 C10 C11 115.10(18) . . ?
C5 C4 C3 122.0(2) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.029
_database_code_depnum_ccdc_archive 'CCDC 1011647'
