# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tc_1
_database_code_depnum_ccdc_archive 'CCDC 1001355'
_audit_update_record             
;
2014-05-06 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H23 N3 O2'
_chemical_formula_sum            'C17 H23 N3 O2'
_chemical_formula_weight         301.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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   'P2(1)/n  '

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

_cell_length_a                   6.8038(3)
_cell_length_b                   17.3110(6)
_cell_length_c                   13.4729(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.2990(10)
_cell_angle_gamma                90.00
_cell_volume                     1565.99(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8732
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      32.01

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.1167
_exptl_crystal_size_mid          0.0684
_exptl_crystal_size_min          0.0535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'SADABS; BRUKER, 2008'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14458
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3420
_reflns_number_gt                2995
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.1000P)²+0.0154P] 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         3420
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1469
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_restrained_S_all      1.240
_refine_ls_shift/su_max          0.001
_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
C3 C 1.20836(15) 0.82759(6) 0.63776(8) 0.0161(2) Uani 1 1 d . . .
C2 C 1.18825(15) 0.90804(6) 0.62042(8) 0.0163(2) Uani 1 1 d . . .
H2 H 1.2748 0.9330 0.5841 0.020 Uiso 1 1 calc R . .
C6 C 0.90718(14) 0.91508(6) 0.71279(7) 0.0153(2) Uani 1 1 d . . .
C1 C 1.04216(15) 0.95028(6) 0.65643(7) 0.0155(2) Uani 1 1 d . . .
C16 C 1.47882(15) 0.82204(6) 0.53520(8) 0.0192(3) Uani 1 1 d . . .
H16A H 1.5998 0.7918 0.5390 0.023 Uiso 1 1 calc R . .
H16B H 1.5154 0.8734 0.5606 0.023 Uiso 1 1 calc R . .
C5 C 0.93289(15) 0.83534(6) 0.73107(8) 0.0173(2) Uani 1 1 d . . .
H5 H 0.8480 0.8106 0.7685 0.021 Uiso 1 1 calc R . .
C4 C 1.07757(16) 0.79227(6) 0.69628(8) 0.0183(3) Uani 1 1 d . . .
H4 H 1.0897 0.7399 0.7112 0.022 Uiso 1 1 calc R . .
C8 C 0.62171(15) 0.94027(6) 0.80809(8) 0.0164(2) Uani 1 1 d . . .
C7 C 0.75680(15) 0.96113(6) 0.74875(7) 0.0161(2) Uani 1 1 d . . .
H7 H 0.7513 1.0125 0.7285 0.019 Uiso 1 1 calc R . .
C14 C 1.36462(15) 0.70188(6) 0.60762(8) 0.0195(3) Uani 1 1 d . . .
H14A H 1.3975 0.6806 0.5458 0.023 Uiso 1 1 calc R . .
H14B H 1.2369 0.6808 0.6172 0.023 Uiso 1 1 calc R . .
C9 C 0.47829(15) 0.99568(6) 0.83961(8) 0.0177(2) Uani 1 1 d . . .
C12 C 0.20554(16) 0.97823(7) 0.94350(9) 0.0244(3) Uani 1 1 d . . .
H12A H 0.0823 0.9610 0.9050 0.037 Uiso 1 1 calc R . .
H12B H 0.2076 1.0337 0.9455 0.037 Uiso 1 1 calc R . .
H12C H 0.2177 0.9584 1.0107 0.037 Uiso 1 1 calc R . .
C10 C 0.44675(15) 0.87578(6) 0.89954(8) 0.0181(3) Uani 1 1 d . . .
C13 C 1.16885(16) 1.06862(6) 0.59958(9) 0.0220(3) Uani 1 1 d . . .
H13A H 1.2934 1.0610 0.6434 0.033 Uiso 1 1 calc R . .
H13B H 1.1372 1.1227 0.5959 0.033 Uiso 1 1 calc R . .
H13C H 1.1791 1.0498 0.5336 0.033 Uiso 1 1 calc R . .
C17 C 1.37847(17) 0.82786(7) 0.42586(8) 0.0235(3) Uani 1 1 d . . .
H17A H 1.3282 0.7781 0.4029 0.035 Uiso 1 1 calc R . .
H17B H 1.4736 0.8451 0.3853 0.035 Uiso 1 1 calc R . .
H17C H 1.2704 0.8641 0.4206 0.035 Uiso 1 1 calc R . .
C11 C 0.36286(17) 0.81368(7) 0.95657(9) 0.0249(3) Uani 1 1 d . . .
H11A H 0.4368 0.7669 0.9526 0.037 Uiso 1 1 calc R . .
H11B H 0.2258 0.8052 0.9282 0.037 Uiso 1 1 calc R . .
H11C H 0.3718 0.8289 1.0257 0.037 Uiso 1 1 calc R . .
C15 C 1.52262(19) 0.67748(7) 0.69517(10) 0.0294(3) Uani 1 1 d . . .
H15A H 1.6516 0.6928 0.6821 0.044 Uiso 1 1 calc R . .
H15B H 1.5192 0.6224 0.7029 0.044 Uiso 1 1 calc R . .
H15C H 1.4967 0.7018 0.7558 0.044 Uiso 1 1 calc R . .
N2 N 0.37079(13) 0.95047(6) 0.89704(7) 0.0187(2) Uani 1 1 d . . .
N3 N 1.34801(13) 0.78609(5) 0.59807(7) 0.0186(2) Uani 1 1 d . . .
N1 N 0.59373(13) 0.86712(5) 0.84973(7) 0.0182(2) Uani 1 1 d . . .
O1 O 1.01504(11) 1.02744(4) 0.63808(6) 0.0215(2) Uani 1 1 d . . .
O2 O 0.45405(12) 1.06519(5) 0.82384(6) 0.0245(2) 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
C3 N3 1.3672(13) . ?
C3 C2 1.4152(14) . ?
C3 C4 1.4192(14) . ?
C2 C1 1.3834(14) . ?
C6 C5 1.4081(15) . ?
C6 C1 1.4200(14) . ?
C6 C7 1.4413(14) . ?
C1 O1 1.3656(12) . ?
C16 N3 1.4631(13) . ?
C16 C17 1.5235(15) . ?
C5 C4 1.3761(14) . ?
C8 C7 1.3609(14) . ?
C8 N1 1.4103(14) . ?
C8 C9 1.4786(14) . ?
C14 N3 1.4661(13) . ?
C14 C15 1.5218(16) . ?
C9 O2 1.2284(14) . ?
C9 N2 1.3889(13) . ?
C12 N2 1.4540(13) . ?
C10 N1 1.2998(13) . ?
C10 N2 1.3908(14) . ?
C10 C11 1.4878(15) . ?
C13 O1 1.4311(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
N3 C3 C2 120.49(9) . . ?
N3 C3 C4 121.92(10) . . ?
C2 C3 C4 117.59(9) . . ?
C1 C2 C3 121.20(9) . . ?
C5 C6 C1 116.19(9) . . ?
C5 C6 C7 123.94(9) . . ?
C1 C6 C7 119.86(9) . . ?
O1 C1 C2 122.49(9) . . ?
O1 C1 C6 115.87(9) . . ?
C2 C1 C6 121.61(9) . . ?
N3 C16 C17 111.62(9) . . ?
C4 C5 C6 123.17(9) . . ?
C5 C4 C3 120.20(10) . . ?
C7 C8 N1 128.27(9) . . ?
C7 C8 C9 122.43(10) . . ?
N1 C8 C9 109.29(8) . . ?
C8 C7 C6 129.36(10) . . ?
N3 C14 C15 112.25(9) . . ?
O2 C9 N2 125.47(9) . . ?
O2 C9 C8 131.46(10) . . ?
N2 C9 C8 103.05(9) . . ?
N1 C10 N2 114.12(9) . . ?
N1 C10 C11 125.07(10) . . ?
N2 C10 C11 120.80(9) . . ?
C9 N2 C10 108.07(8) . . ?
C9 N2 C12 124.55(9) . . ?
C10 N2 C12 127.37(9) . . ?
C3 N3 C16 121.94(9) . . ?
C3 N3 C14 122.46(9) . . ?
C16 N3 C14 115.36(8) . . ?
C10 N1 C8 105.45(9) . . ?
C1 O1 C13 117.88(8) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.043
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_momimre
_database_code_depnum_ccdc_archive 'CCDC 1001357'
_audit_update_record             
;
2014-05-06 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H23 N3 O2'
_chemical_formula_sum            'C17 H23 N3 O2'
_chemical_formula_weight         301.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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   'P2(1)/n  '

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

_cell_length_a                   10.896(6)
_cell_length_b                   7.886(5)
_cell_length_c                   19.222(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.135(12)
_cell_angle_gamma                90.00
_cell_volume                     1647.4(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2452
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      23.46

_exptl_crystal_description       rectangular
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.0856
_exptl_crystal_size_min          0.035
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS; BRUKER, 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8612
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         24.98
_reflns_number_total             2450
_reflns_number_gt                1579
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.2000P)²+0.0000P] 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         2450
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1602
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.2356
_refine_ls_wR_factor_gt          0.2239
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_restrained_S_all      1.242
_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 0.7004(4) 0.6729(5) 0.5920(2) 0.0619(12) Uani 1 1 d . . .
O2 O 0.9095(3) 0.9901(4) 0.4148(2) 0.0480(11) Uani 1 1 d . . .
N1 N 0.5013(3) 0.9928(4) 0.2217(2) 0.0449(12) Uani 1 1 d . . .
N2 N 0.4752(3) 0.7828(4) 0.4582(2) 0.0372(11) Uani 1 1 d . . .
N3 N 0.4895(4) 0.6710(4) 0.5672(2) 0.0430(12) Uani 1 1 d . . .
C1 C 0.5218(5) 1.0628(6) 0.0969(3) 0.0594(16) Uani 1 1 d . . .
H1A H 0.6055 1.0240 0.1011 0.089 Uiso 1 1 calc R . .
H1B H 0.5142 1.1553 0.0644 0.089 Uiso 1 1 calc R . .
H1C H 0.4688 0.9717 0.0805 0.089 Uiso 1 1 calc R . .
C2 C 0.4855(4) 1.1214(5) 0.1670(3) 0.0436(13) Uani 1 1 d . . .
H2A H 0.5344 1.2200 0.1811 0.052 Uiso 1 1 calc R . .
H2B H 0.3999 1.1561 0.1626 0.052 Uiso 1 1 calc R . .
C5 C 0.6029(4) 0.9963(4) 0.2696(3) 0.0373(13) Uani 1 1 d . . .
C10 C 0.6018(4) 0.9147(4) 0.3337(3) 0.0345(12) Uani 1 1 d . . .
H4 H 0.5305 0.8591 0.3447 0.041 Uiso 1 1 calc R . .
C9 C 0.7033(4) 0.9130(4) 0.3823(3) 0.0348(12) Uani 1 1 d . . .
C11 C 0.6994(4) 0.8332(5) 0.4501(3) 0.0367(12) Uani 1 1 d . . .
H6 H 0.7754 0.8173 0.4745 0.044 Uiso 1 1 calc R . .
C13 C 0.6000(4) 0.7780(5) 0.4831(2) 0.0342(12) Uani 1 1 d . . .
C15 C 0.4159(4) 0.7214(5) 0.5097(3) 0.0432(14) Uani 1 1 d . . .
C16 C 0.2792(4) 0.7009(6) 0.5047(3) 0.0567(17) Uani 1 1 d . . .
H9A H 0.2439 0.7661 0.4662 0.085 Uiso 1 1 calc R . .
H9B H 0.2472 0.7399 0.5471 0.085 Uiso 1 1 calc R . .
H9C H 0.2588 0.5834 0.4977 0.085 Uiso 1 1 calc R . .
C17 C 0.4507(5) 0.6008(6) 0.6315(3) 0.0615(17) Uani 1 1 d . . .
H10 H 0.4035 0.6838 0.6545 0.092 Uiso 1 1 calc R . .
H10B H 0.5218 0.5702 0.6612 0.092 Uiso 1 1 calc R . .
H10C H 0.4012 0.5020 0.6214 0.092 Uiso 1 1 calc R . .
C14 C 0.6104(5) 0.7033(5) 0.5537(3) 0.0462(15) Uani 1 1 d . . .
C6 C 0.7140(4) 1.0782(5) 0.2553(3) 0.0419(14) Uani 1 1 d . . .
H12 H 0.7182 1.1343 0.2130 0.050 Uiso 1 1 calc R . .
C7 C 0.8147(4) 1.0775(5) 0.3014(3) 0.0407(14) Uani 1 1 d . . .
H13 H 0.8858 1.1331 0.2900 0.049 Uiso 1 1 calc R . .
C8 C 0.8130(4) 0.9951(5) 0.3651(3) 0.0360(13) Uani 1 1 d . . .
C12 C 1.0244(4) 1.0627(6) 0.3986(3) 0.0564(16) Uani 1 1 d . . .
H15A H 1.0548 1.0039 0.3596 0.085 Uiso 1 1 calc R . .
H15B H 1.0828 1.0525 0.4382 0.085 Uiso 1 1 calc R . .
H15C H 1.0128 1.1803 0.3870 0.085 Uiso 1 1 calc R . .
C3 C 0.3907(4) 0.8966(5) 0.2356(3) 0.0424(13) Uani 1 1 d . . .
H16A H 0.4156 0.7883 0.2560 0.051 Uiso 1 1 calc R . .
H16B H 0.3446 0.8737 0.1915 0.051 Uiso 1 1 calc R . .
C4 C 0.3060(4) 0.9844(6) 0.2839(3) 0.0616(17) Uani 1 1 d . . .
H17A H 0.3500 1.0058 0.3281 0.092 Uiso 1 1 calc R . .
H17B H 0.2365 0.9129 0.2906 0.092 Uiso 1 1 calc R . .
H17C H 0.2780 1.0898 0.2635 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 C14 1.206(6) . ?
O2 C8 1.369(6) . ?
O2 C12 1.432(5) . ?
N1 C5 1.387(6) . ?
N1 C2 1.462(6) . ?
N1 C3 1.465(5) . ?
N2 C15 1.313(6) . ?
N2 C13 1.410(6) . ?
N3 C15 1.376(7) . ?
N3 C14 1.385(6) . ?
N3 C17 1.445(6) . ?
C1 C2 1.504(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 C10 1.392(7) . ?
C5 C6 1.417(6) . ?
C10 C9 1.396(7) . ?
C10 H4 0.9300 . ?
C9 C8 1.419(5) . ?
C9 C11 1.450(7) . ?
C11 C13 1.366(5) . ?
C11 H6 0.9300 . ?
C13 C14 1.477(8) . ?
C15 C16 1.494(7) . ?
C16 H9A 0.9600 . ?
C16 H9B 0.9600 . ?
C16 H9C 0.9600 . ?
C17 H10 0.9600 . ?
C17 H10B 0.9600 . ?
C17 H10C 0.9600 . ?
C6 C7 1.360(7) . ?
C6 H12 0.9300 . ?
C7 C8 1.389(7) . ?
C7 H13 0.9300 . ?
C12 H15A 0.9600 . ?
C12 H15B 0.9600 . ?
C12 H15C 0.9600 . ?
C3 C4 1.522(6) . ?
C3 H16A 0.9700 . ?
C3 H16B 0.9700 . ?
C4 H17A 0.9600 . ?
C4 H17B 0.9600 . ?
C4 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C12 118.4(4) . . ?
C5 N1 C2 120.7(3) . . ?
C5 N1 C3 121.2(4) . . ?
C2 N1 C3 115.7(4) . . ?
C15 N2 C13 104.4(4) . . ?
C15 N3 C14 107.7(4) . . ?
C15 N3 C17 127.5(4) . . ?
C14 N3 C17 124.8(5) . . ?
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 . . ?
N1 C2 C1 114.0(4) . . ?
N1 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N1 C5 C10 121.4(3) . . ?
N1 C5 C6 122.2(4) . . ?
C10 C5 C6 116.4(5) . . ?
C5 C10 C9 122.7(4) . . ?
C5 C10 H4 118.6 . . ?
C9 C10 H4 118.6 . . ?
C10 C9 C8 118.7(4) . . ?
C10 C9 C11 122.2(3) . . ?
C8 C9 C11 119.1(4) . . ?
C13 C11 C9 129.2(4) . . ?
C13 C11 H6 115.4 . . ?
C9 C11 H6 115.4 . . ?
C11 C13 N2 127.7(4) . . ?
C11 C13 C14 122.9(5) . . ?
N2 C13 C14 109.3(3) . . ?
N2 C15 N3 115.0(4) . . ?
N2 C15 C16 122.3(5) . . ?
N3 C15 C16 122.7(4) . . ?
C15 C16 H9A 109.5 . . ?
C15 C16 H9B 109.5 . . ?
H9A C16 H9B 109.5 . . ?
C15 C16 H9C 109.5 . . ?
H9A C16 H9C 109.5 . . ?
H9B C16 H9C 109.5 . . ?
N3 C17 H10 109.5 . . ?
N3 C17 H10B 109.5 . . ?
H10 C17 H10B 109.5 . . ?
N3 C17 H10C 109.5 . . ?
H10 C17 H10C 109.5 . . ?
H10B C17 H10C 109.5 . . ?
O1 C14 N3 126.3(5) . . ?
O1 C14 C13 130.2(4) . . ?
N3 C14 C13 103.5(5) . . ?
C7 C6 C5 122.2(5) . . ?
C7 C6 H12 118.9 . . ?
C5 C6 H12 118.9 . . ?
C6 C7 C8 121.1(4) . . ?
C6 C7 H13 119.5 . . ?
C8 C7 H13 119.5 . . ?
O2 C8 C7 124.8(4) . . ?
O2 C8 C9 116.2(4) . . ?
C7 C8 C9 118.9(5) . . ?
O2 C12 H15A 109.5 . . ?
O2 C12 H15B 109.5 . . ?
H15A C12 H15B 109.5 . . ?
O2 C12 H15C 109.5 . . ?
H15A C12 H15C 109.5 . . ?
H15B C12 H15C 109.5 . . ?
N1 C3 C4 114.7(4) . . ?
N1 C3 H16A 108.6 . . ?
C4 C3 H16A 108.6 . . ?
N1 C3 H16B 108.6 . . ?
C4 C3 H16B 108.6 . . ?
H16A C3 H16B 107.6 . . ?
C3 C4 H17A 109.5 . . ?
C3 C4 H17B 109.5 . . ?
H17A C4 H17B 109.5 . . ?
C3 C4 H17C 109.5 . . ?
H17A C4 H17C 109.5 . . ?
H17B C4 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.162
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tc_1
_database_code_depnum_ccdc_archive 'CCDC 1001358'
_audit_update_record             
;
2014-05-06 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 N2 O3'
_chemical_formula_sum            'C16 H20 N2 O3'
_chemical_formula_weight         288.34

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   P2(1)/n

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

_cell_length_a                   7.1834(5)
_cell_length_b                   12.7135(8)
_cell_length_c                   16.5140(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.201(2)
_cell_angle_gamma                90.00
_cell_volume                     1496.26(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8718
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      31.94

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.0856
_exptl_crystal_size_min          0.0351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS; BRUKER, 2008'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13767
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3258
_reflns_number_gt                2860
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.1000P)²+0.8377P] 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         3258
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   0.754
_refine_ls_restrained_S_all      0.754
_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
C5 C -0.09942(15) 0.28025(8) -0.01008(6) 0.0171(2) Uani 1 1 d . . .
C1 C 0.07170(15) 0.35916(8) 0.11114(6) 0.0172(2) Uani 1 1 d . . .
C2 C 0.22843(15) 0.29230(8) 0.10674(6) 0.0167(2) Uani 1 1 d . . .
C13 C 0.55182(15) 0.24432(8) 0.17472(6) 0.0171(2) Uani 1 1 d . . .
C6 C -0.08725(15) 0.35356(9) 0.05487(7) 0.0176(2) Uani 1 1 d . . .
H6 H -0.1875 0.3985 0.0597 0.021 Uiso 1 1 calc R . .
C3 C 0.21434(15) 0.22129(8) 0.04076(7) 0.0180(2) Uani 1 1 d . . .
H3 H 0.3148 0.1767 0.0357 0.022 Uiso 1 1 calc R . .
C4 C 0.05883(16) 0.21520(9) -0.01618(7) 0.0192(2) Uani 1 1 d . . .
H4 H 0.0569 0.1680 -0.0593 0.023 Uiso 1 1 calc R . .
C12 C 0.38955(15) 0.30091(8) 0.16645(6) 0.0172(2) Uani 1 1 d . . .
H12 H 0.3827 0.3529 0.2055 0.021 Uiso 1 1 calc R . .
C14 C 0.70194(15) 0.26170(9) 0.24136(7) 0.0201(2) Uani 1 1 d . . .
C7 C -0.42771(15) 0.33089(9) -0.05504(7) 0.0200(2) Uani 1 1 d . . .
H7A H -0.4393 0.3374 0.0026 0.024 Uiso 1 1 calc R . .
H7B H -0.5353 0.2916 -0.0804 0.024 Uiso 1 1 calc R . .
C15 C 0.76718(15) 0.13270(9) 0.15963(7) 0.0188(2) Uani 1 1 d . . .
C9 C -0.27149(16) 0.19761(10) -0.13242(7) 0.0237(3) Uani 1 1 d . . .
H9A H -0.1503 0.1914 -0.1521 0.028 Uiso 1 1 calc R . .
H9B H -0.3599 0.2244 -0.1768 0.028 Uiso 1 1 calc R . .
C16 C 0.88901(17) 0.04881(10) 0.13395(8) 0.0257(3) Uani 1 1 d . . .
H16A H 0.8318 0.0186 0.0836 0.039 Uiso 1 1 calc R . .
H16B H 0.9056 -0.0047 0.1753 0.039 Uiso 1 1 calc R . .
H16C H 1.0089 0.0779 0.1263 0.039 Uiso 1 1 calc R . .
C8 C -0.42976(17) 0.43982(9) -0.09272(8) 0.0266(3) Uani 1 1 d . . .
H8A H -0.3262 0.4800 -0.0664 0.040 Uiso 1 1 calc R . .
H8B H -0.5453 0.4745 -0.0856 0.040 Uiso 1 1 calc R . .
H8C H -0.4190 0.4339 -0.1499 0.040 Uiso 1 1 calc R . .
C11 C -0.04757(17) 0.50918(10) 0.17595(8) 0.0260(3) Uani 1 1 d . . .
H11A H -0.0623 0.5459 0.1248 0.039 Uiso 1 1 calc R . .
H11B H -0.0083 0.5577 0.2193 0.039 Uiso 1 1 calc R . .
H11C H -0.1650 0.4780 0.1848 0.039 Uiso 1 1 calc R . .
C10 C -0.33509(19) 0.08955(10) -0.10831(9) 0.0321(3) Uani 1 1 d . . .
H10A H -0.2454 0.0614 -0.0659 0.048 Uiso 1 1 calc R . .
H10B H -0.3449 0.0438 -0.1549 0.048 Uiso 1 1 calc R . .
H10C H -0.4552 0.0952 -0.0889 0.048 Uiso 1 1 calc R . .
N1 N -0.25670(13) 0.27260(8) -0.06468(6) 0.0193(2) Uani 1 1 d . . .
N2 N 0.60479(13) 0.16133(7) 0.12617(6) 0.0186(2) Uani 1 1 d . . .
O3 O 0.83826(11) 0.18683(6) 0.22936(5) 0.0212(2) Uani 1 1 d . . .
O2 O 0.72353(12) 0.32128(7) 0.29819(5) 0.0289(2) Uani 1 1 d . . .
O1 O 0.09050(11) 0.42876(6) 0.17447(5) 0.0221(2) 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
C5 N1 1.3577(14) . ?
C5 C6 1.4154(15) . ?
C5 C4 1.4195(15) . ?
C1 O1 1.3637(13) . ?
C1 C6 1.3807(15) . ?
C1 C2 1.4198(15) . ?
C2 C3 1.4088(15) . ?
C2 C12 1.4275(15) . ?
C13 C12 1.3621(15) . ?
C13 N2 1.4061(14) . ?
C13 C14 1.4579(15) . ?
C3 C4 1.3692(15) . ?
C14 O2 1.2008(14) . ?
C14 O3 1.3975(13) . ?
C7 N1 1.4603(14) . ?
C7 C8 1.5175(16) . ?
C15 N2 1.2794(14) . ?
C15 O3 1.3831(14) . ?
C15 C16 1.4752(16) . ?
C9 N1 1.4636(14) . ?
C9 C10 1.5166(18) . ?
C11 O1 1.4268(13) . ?

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 C5 C6 121.17(10) . . ?
N1 C5 C4 121.22(10) . . ?
C6 C5 C4 117.61(10) . . ?
O1 C1 C6 122.93(10) . . ?
O1 C1 C2 115.14(9) . . ?
C6 C1 C2 121.93(10) . . ?
C3 C2 C1 116.27(10) . . ?
C3 C2 C12 123.84(10) . . ?
C1 C2 C12 119.88(10) . . ?
C12 C13 N2 128.94(10) . . ?
C12 C13 C14 122.58(10) . . ?
N2 C13 C14 108.46(9) . . ?
C1 C6 C5 120.75(10) . . ?
C4 C3 C2 122.73(10) . . ?
C3 C4 C5 120.67(10) . . ?
C13 C12 C2 129.67(10) . . ?
O2 C14 O3 121.09(10) . . ?
O2 C14 C13 134.14(11) . . ?
O3 C14 C13 104.77(9) . . ?
N1 C7 C8 112.55(9) . . ?
N2 C15 O3 116.07(10) . . ?
N2 C15 C16 128.55(11) . . ?
O3 C15 C16 115.38(10) . . ?
N1 C9 C10 112.63(10) . . ?
C5 N1 C7 122.19(9) . . ?
C5 N1 C9 121.93(9) . . ?
C7 N1 C9 115.62(9) . . ?
C15 N2 C13 105.34(9) . . ?
C15 O3 C14 105.36(8) . . ?
C1 O1 C11 118.42(9) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.043
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tmc_1
_database_code_depnum_ccdc_archive 'CCDC 1001359'
_audit_update_record             
;
2014-05-06 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 N2 O3'
_chemical_formula_sum            'C16 H20 N2 O3'
_chemical_formula_weight         288.34

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   'P2(1)/n  '

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

_cell_length_a                   13.818(6)
_cell_length_b                   7.428(3)
_cell_length_c                   15.482(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.055(9)
_cell_angle_gamma                90.00
_cell_volume                     1587.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2633
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      19.33

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.035
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19644
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.14
_reflns_number_total             2817
_reflns_number_gt                1333
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXS-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)+(0.1000P)²+0.4375P] 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         2817
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1499
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_ref         0.2317
_refine_ls_wR_factor_gt          0.1998
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_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
C1 C 0.5823(8) 1.183(2) 0.3414(5) 0.305(10) Uani 1 1 d . C .
H1A H 0.6435 1.1308 0.3288 0.457 Uiso 1 1 calc R . .
H1B H 0.5921 1.3047 0.3609 0.457 Uiso 1 1 calc R . .
H1C H 0.5401 1.1825 0.2901 0.457 Uiso 1 1 calc R . .
C2 C 0.5461(10) 1.0966(14) 0.3971(10) 0.286(8) Uani 1 1 d . . .
H2A H 0.4852 1.1434 0.4159 0.343 Uiso 1 1 calc R A 1
H2B H 0.5899 1.0631 0.4455 0.343 Uiso 1 1 calc R A 1
C3 C 0.6391(6) 0.8134(10) 0.2803(5) 0.197(4) Uani 1 1 d . . .
H3A H 0.6342 0.7641 0.2222 0.236 Uiso 1 1 calc R B 1
H3B H 0.7003 0.8746 0.2924 0.236 Uiso 1 1 calc R B 1
C4 C 0.6147(7) 0.7084(17) 0.3381(6) 0.256(5) Uani 1 1 d . C .
H4A H 0.6291 0.7620 0.3937 0.385 Uiso 1 1 calc R . .
H4B H 0.6498 0.5975 0.3341 0.385 Uiso 1 1 calc R . .
H4C H 0.5464 0.6849 0.3310 0.385 Uiso 1 1 calc R . .
C5 C 0.4572(3) 0.9316(6) 0.2517(3) 0.0931(12) Uani 1 1 d . . .
C6 C 0.3855(3) 1.0632(6) 0.2517(3) 0.1022(13) Uani 1 1 d . C .
H6 H 0.3949 1.1628 0.2875 0.123 Uiso 1 1 calc R . .
C7 C 0.3017(3) 1.0510(6) 0.2008(3) 0.0941(12) Uani 1 1 d . . .
H7 H 0.2559 1.1425 0.2019 0.113 Uiso 1 1 calc R C .
C8 C 0.2852(3) 0.9060(6) 0.1487(2) 0.0822(11) Uani 1 1 d . C .
C9 C 0.3544(2) 0.7680(5) 0.1469(2) 0.0743(10) Uani 1 1 d . . .
C10 C 0.4388(3) 0.7849(5) 0.1986(2) 0.0820(10) Uani 1 1 d . C .
H10 H 0.4849 0.6938 0.1975 0.098 Uiso 1 1 calc R . .
C11 C 0.3354(2) 0.6128(6) 0.0922(2) 0.0823(11) Uani 1 1 d . C .
H11 H 0.2749 0.6117 0.0629 0.099 Uiso 1 1 calc R . .
C12 C 0.3919(3) 0.4694(5) 0.0772(2) 0.0774(10) Uani 1 1 d . . .
C13 C 0.3628(3) 0.3241(7) 0.0167(3) 0.1042(13) Uani 1 1 d . C .
C14 C 0.5067(3) 0.2781(6) 0.0779(2) 0.0836(10) Uani 1 1 d . . .
C15 C 0.5964(3) 0.1735(6) 0.0930(3) 0.1061(14) Uani 1 1 d . C .
H15A H 0.6439 0.2456 0.1245 0.159 Uiso 1 1 calc R . .
H15B H 0.6208 0.1389 0.0386 0.159 Uiso 1 1 calc R . .
H15C H 0.5830 0.0676 0.1259 0.159 Uiso 1 1 calc R . .
C16 C 0.13447(10) 1.0232(2) 0.09123(9) 0.142(2) Uani 1 1 d . C .
H16A H 0.1120 1.0448 0.1479 0.213 Uiso 1 1 calc R . .
H16B H 0.0807 0.9896 0.0528 0.213 Uiso 1 1 calc R . .
H16C H 0.1638 1.1307 0.0702 0.213 Uiso 1 1 calc R . .
N1A N 0.53526(14) 0.9340(3) 0.31098(13) 0.135(4) Uani 0.50 1 d PR C 1
N1B N 0.54736(13) 0.9587(2) 0.29178(13) 0.121(4) Uani 0.50 1 d PR C 2
N2 N 0.48361(10) 0.4285(2) 0.11221(15) 0.0794(9) Uani 1 1 d R C .
O1 O 0.20341(10) 0.8828(2) 0.09526(9) 0.1067(9) Uani 1 1 d R . .
O2 O 0.43966(11) 0.2057(2) 0.01993(12) 0.1012(9) Uani 1 1 d R C .
O3 O 0.29214(11) 0.3007(2) -0.02913(13) 0.1452(14) Uani 1 1 d 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
C1 C2 1.205(16) . ?
C2 N1A 1.800(14) . ?
C2 N1B 1.927(15) . ?
C3 C4 1.247(10) . ?
C3 N1B 1.681(9) . ?
C3 N1A 1.777(10) . ?
C5 N1B 1.376(4) . ?
C5 N1A 1.378(4) . ?
C5 C10 1.381(5) . ?
C5 C6 1.392(5) . ?
C6 C7 1.369(6) . ?
C7 C8 1.358(6) . ?
C8 O1 1.375(4) . ?
C8 C9 1.404(5) . ?
C9 C10 1.385(5) . ?
C9 C11 1.446(5) . ?
C11 C12 1.348(5) . ?
C12 N2 1.386(4) . ?
C12 C13 1.470(6) . ?
C13 O3 1.189(4) . ?
C13 O2 1.377(5) . ?
C14 N2 1.285(4) . ?
C14 O2 1.365(4) . ?
C14 C15 1.471(6) . ?
C16 O1 1.4117 . ?

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
C1 C2 N1A 81.3(12) . . ?
C1 C2 N1B 69.8(11) . . ?
N1A C2 N1B 11.50(10) . . ?
C4 C3 N1B 95.3(9) . . ?
C4 C3 N1A 82.6(9) . . ?
N1B C3 N1A 12.69(8) . . ?
N1B C5 N1A 16.45(5) . . ?
N1B C5 C10 121.2(3) . . ?
N1A C5 C10 121.3(3) . . ?
N1B C5 C6 121.6(4) . . ?
N1A C5 C6 121.5(4) . . ?
C10 C5 C6 116.5(4) . . ?
C7 C6 C5 122.3(4) . . ?
C8 C7 C6 120.4(4) . . ?
C7 C8 O1 124.3(4) . . ?
C7 C8 C9 119.8(4) . . ?
O1 C8 C9 115.8(4) . . ?
C10 C9 C8 118.5(4) . . ?
C10 C9 C11 122.1(3) . . ?
C8 C9 C11 119.4(3) . . ?
C5 C10 C9 122.6(4) . . ?
C12 C11 C9 130.0(3) . . ?
C11 C12 N2 129.2(3) . . ?
C11 C12 C13 123.3(4) . . ?
N2 C12 C13 107.5(3) . . ?
O3 C13 O2 122.4(4) . . ?
O3 C13 C12 132.4(4) . . ?
O2 C13 C12 105.2(3) . . ?
N2 C14 O2 116.0(3) . . ?
N2 C14 C15 128.3(3) . . ?
O2 C14 C15 115.7(3) . . ?
C5 N1A C3 115.5(3) . . ?
C5 N1A C2 122.2(4) . . ?
C3 N1A C2 120.0(5) . . ?
C5 N1B C3 121.9(3) . . ?
C5 N1B C2 114.2(4) . . ?
C3 N1B C2 118.1(4) . . ?
C14 N2 C12 105.7(3) . . ?
C8 O1 C16 117.70(19) . . ?
C14 O2 C13 105.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.14
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.044
