# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_d37
_database_code_depnum_ccdc_archive 'CCDC 1020677'
_audit_update_record             
;
2014-08-21 deposited with the CCDC.
2015-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          398
_chemical_formula_moiety         chno
_chemical_formula_sum            'C14 H16 N2 O2'
_chemical_formula_weight         244.29

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           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   7.6022(17)
_cell_length_b                   8.3944(18)
_cell_length_c                   11.562(2)
_cell_angle_alpha                106.836(18)
_cell_angle_beta                 102.222(17)
_cell_angle_gamma                102.304(19)
_cell_volume                     659.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1536
_cell_measurement_theta_min      3.7550
_cell_measurement_theta_max      29.0276

_exptl_crystal_description       cuboid
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260.0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5025
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.78
_diffrn_reflns_theta_max         29.09
_reflns_number_total             3538
_reflns_number_gt                2017
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0681P)²+0.0185P] 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         2924
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.003
_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
N2 N 0.28143(17) 0.91030(17) 0.80500(11) 0.0494(3) Uani 1 1 d . . .
C1 C 0.24758(17) 0.61853(19) 1.04496(12) 0.0404(3) Uani 1 1 d . . .
C7 C 0.23599(17) 0.5072(2) 1.11808(13) 0.0429(3) Uani 1 1 d . . .
H7 H 0.2573 0.4016 1.0813 0.051 Uiso 1 1 calc R . .
C6 C 0.21763(18) 0.7832(2) 1.07513(13) 0.0446(4) Uani 1 1 d . . .
H6 H 0.1888 0.8285 1.1499 0.053 Uiso 1 1 calc R . .
C2 C 0.29304(19) 0.5592(2) 0.93144(13) 0.0453(4) Uani 1 1 d . . .
H2 H 0.3146 0.4509 0.9083 0.054 Uiso 1 1 calc R . .
C5 C 0.22961(19) 0.8793(2) 0.99779(13) 0.0448(3) Uani 1 1 d . . .
H5 H 0.2083 0.9876 1.0212 0.054 Uiso 1 1 calc R . .
O2 O 0.16040(15) 0.41776(16) 1.39144(10) 0.0629(4) Uani 1 1 d . . .
C8 C 0.20006(18) 0.5255(2) 1.23036(13) 0.0456(4) Uani 1 1 d . . .
C10 C 0.19597(19) 0.3805(2) 1.27933(14) 0.0494(4) Uani 1 1 d . . .
C3 C 0.3069(2) 0.6535(2) 0.85389(13) 0.0469(4) Uani 1 1 d . . .
H3 H 0.3389 0.6089 0.7803 0.056 Uiso 1 1 calc R . .
O1 O 0.22209(16) 0.24614(17) 1.22575(11) 0.0672(4) Uani 1 1 d . . .
C14 C 0.2480(2) 1.0783(2) 0.83683(17) 0.0608(4) Uani 1 1 d . . .
H14 H 0.3441 1.1583 0.9118 0.091 Uiso 1 1 calc R . .
H14C H 0.1271 1.0676 0.8515 0.091 Uiso 1 1 calc R . .
H14B H 0.2507 1.1209 0.7684 0.091 Uiso 1 1 calc R . .
C9 C 0.1648(2) 0.6773(3) 1.30462(15) 0.0590(4) Uani 1 1 d . . .
C13 C 0.3496(2) 0.8557(3) 0.69561(16) 0.0639(5) Uani 1 1 d . . .
H13A H 0.4766 0.8521 0.7230 0.096 Uiso 1 1 calc R . .
H13C H 0.3462 0.9369 0.6519 0.096 Uiso 1 1 calc R . .
H13B H 0.2709 0.7420 0.6398 0.096 Uiso 1 1 calc R . .
C11 C 0.1535(3) 0.2857(3) 1.44970(18) 0.0747(6) Uani 1 1 d . . .
H11B H 0.1049 0.1714 1.3841 0.090 Uiso 1 1 calc R . .
H11A H 0.0676 0.2954 1.5008 0.090 Uiso 1 1 calc R . .
C12 C 0.3391(3) 0.3021(3) 1.52919(19) 0.0846(6) Uani 1 1 d . . .
H12C H 0.4212 0.2812 1.4775 0.127 Uiso 1 1 calc R . .
H12B H 0.3266 0.2185 1.5709 0.127 Uiso 1 1 calc R . .
H12A H 0.3909 0.4174 1.5912 0.127 Uiso 1 1 calc R . .
C4 C 0.27367(17) 0.81736(19) 0.88319(12) 0.0405(3) Uani 1 1 d . . .
N1 N 0.1366(3) 0.7988(3) 1.36345(16) 0.0909(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0609(7) 0.0466(8) 0.0488(7) 0.0207(6) 0.0199(6) 0.0225(6)
C1 0.0364(6) 0.0424(8) 0.0403(7) 0.0116(6) 0.0104(5) 0.0122(6)
C7 0.0404(7) 0.0447(9) 0.0445(7) 0.0162(7) 0.0110(6) 0.0146(6)
C6 0.0460(7) 0.0489(9) 0.0406(7) 0.0122(7) 0.0167(6) 0.0187(7)
C2 0.0543(8) 0.0386(8) 0.0458(8) 0.0122(7) 0.0172(6) 0.0199(7)
C5 0.0494(8) 0.0397(8) 0.0468(8) 0.0126(7) 0.0153(6) 0.0184(7)
O2 0.0706(7) 0.0757(9) 0.0537(7) 0.0349(7) 0.0233(5) 0.0219(6)
C8 0.0416(7) 0.0521(10) 0.0439(8) 0.0181(7) 0.0108(6) 0.0154(7)
C10 0.0416(7) 0.0600(11) 0.0489(8) 0.0247(8) 0.0107(6) 0.0146(7)
C3 0.0576(8) 0.0458(9) 0.0415(7) 0.0117(7) 0.0214(6) 0.0222(7)
O1 0.0847(8) 0.0645(9) 0.0683(8) 0.0327(7) 0.0287(6) 0.0342(7)
C14 0.0756(10) 0.0501(10) 0.0654(10) 0.0267(9) 0.0212(8) 0.0262(9)
C9 0.0786(11) 0.0645(12) 0.0449(8) 0.0244(9) 0.0263(8) 0.0276(9)
C13 0.0797(11) 0.0736(13) 0.0551(10) 0.0324(10) 0.0303(8) 0.0322(10)
C11 0.0761(11) 0.0905(15) 0.0656(11) 0.0461(11) 0.0211(9) 0.0142(11)
C12 0.0925(14) 0.0967(17) 0.0719(12) 0.0427(13) 0.0184(11) 0.0298(13)
C4 0.0364(6) 0.0414(8) 0.0413(7) 0.0126(6) 0.0088(5) 0.0116(6)
N1 0.1551(17) 0.0797(13) 0.0659(10) 0.0314(10) 0.0594(11) 0.0553(13)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
N2 C4 1.3568(17) . ?
N2 C14 1.442(2) . ?
N2 C13 1.4564(19) . ?
C1 C6 1.405(2) . ?
C1 C2 1.4059(18) . ?
C1 C7 1.4316(19) . ?
C7 C8 1.3550(19) . ?
C7 H7 0.9300 . ?
C6 C5 1.371(2) . ?
C6 H6 0.9300 . ?
C2 C3 1.3630(19) . ?
C2 H2 0.9300 . ?
C5 C4 1.4147(19) . ?
C5 H5 0.9300 . ?
O2 C10 1.3418(18) . ?
O2 C11 1.452(2) . ?
C8 C9 1.429(2) . ?
C8 C10 1.481(2) . ?
C10 O1 1.1990(19) . ?
C3 C4 1.409(2) . ?
C3 H3 0.9300 . ?
C14 H14 0.9600 . ?
C14 H14C 0.9600 . ?
C14 H14B 0.9600 . ?
C9 N1 1.141(2) . ?
C13 H13A 0.9600 . ?
C13 H13C 0.9600 . ?
C13 H13B 0.9600 . ?
C11 C12 1.466(3) . ?
C11 H11B 0.9700 . ?
C11 H11A 0.9700 . ?
C12 H12C 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12A 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
C4 N2 C14 121.07(12) . . ?
C4 N2 C13 120.95(13) . . ?
C14 N2 C13 117.42(13) . . ?
C6 C1 C2 115.95(12) . . ?
C6 C1 C7 126.39(12) . . ?
C2 C1 C7 117.67(13) . . ?
C8 C7 C1 132.63(15) . . ?
C8 C7 H7 113.7 . . ?
C1 C7 H7 113.7 . . ?
C5 C6 C1 122.04(13) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
C3 C2 C1 122.80(13) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C6 C5 C4 121.45(13) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C10 O2 C11 117.12(15) . . ?
C7 C8 C9 123.62(14) . . ?
C7 C8 C10 118.60(14) . . ?
C9 C8 C10 117.78(13) . . ?
O1 C10 O2 123.94(15) . . ?
O1 C10 C8 124.21(14) . . ?
O2 C10 C8 111.85(14) . . ?
C2 C3 C4 121.19(13) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
N2 C14 H14 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14 C14 H14C 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14 C14 H14B 109.5 . . ?
H14C C14 H14B 109.5 . . ?
N1 C9 C8 179.70(17) . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13C C13 H13B 109.5 . . ?
O2 C11 C12 112.21(16) . . ?
O2 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
O2 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
H11B C11 H11A 107.9 . . ?
C11 C12 H12C 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
H12C C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?
N2 C4 C3 121.82(12) . . ?
N2 C4 C5 121.62(13) . . ?
C3 C4 C5 116.56(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C7 C8 -1.6(2) . . . . ?
C2 C1 C7 C8 178.47(14) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C7 C1 C6 C5 -179.11(12) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
C7 C1 C2 C3 179.61(13) . . . . ?
C1 C6 C5 C4 -0.2(2) . . . . ?
C1 C7 C8 C9 -0.6(2) . . . . ?
C1 C7 C8 C10 179.13(13) . . . . ?
C11 O2 C10 O1 -0.1(2) . . . . ?
C11 O2 C10 C8 -179.76(12) . . . . ?
C7 C8 C10 O1 -0.2(2) . . . . ?
C9 C8 C10 O1 179.54(15) . . . . ?
C7 C8 C10 O2 179.48(12) . . . . ?
C9 C8 C10 O2 -0.78(19) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C7 C8 C9 N1 14(39) . . . . ?
C10 C8 C9 N1 -166(100) . . . . ?
C10 O2 C11 C12 88.5(2) . . . . ?
C14 N2 C4 C3 -179.66(13) . . . . ?
C13 N2 C4 C3 -8.5(2) . . . . ?
C14 N2 C4 C5 1.1(2) . . . . ?
C13 N2 C4 C5 172.27(13) . . . . ?
C2 C3 C4 N2 -177.98(12) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C6 C5 C4 N2 178.47(12) . . . . ?
C6 C5 C4 C3 -0.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.826
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_mcadmab
_database_code_depnum_ccdc_archive 'CCDC 1020678'
_audit_update_record             
;
2014-08-21 deposited with the CCDC.
2015-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          317
_chemical_formula_moiety         CHNO
_chemical_formula_sum            'C13 H14 N2 O2'
_chemical_formula_weight         230.26

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           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   7.3225(14)
_cell_length_b                   7.4824(14)
_cell_length_c                   11.5556(16)
_cell_angle_alpha                100.830(13)
_cell_angle_beta                 104.334(14)
_cell_angle_gamma                96.663(15)
_cell_volume                     593.64(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1104
_cell_measurement_theta_min      3.6819
_cell_measurement_theta_max      29.0436

_exptl_crystal_description       cuboid
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98876
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4303
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.69
_diffrn_reflns_theta_max         29.11
_reflns_number_total             2659
_reflns_number_gt                1818
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0513P)²+0.0794P] 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         2659
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1327
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
C7 C 0.3233(2) 0.6702(2) 0.44747(15) 0.0385(4) Uani 1 1 d . . .
H7 H 0.3870 0.7889 0.4878 0.046 Uiso 1 1 calc R . .
O2 O 0.2765(2) 0.74468(16) 0.14542(11) 0.0535(4) Uani 1 1 d . . .
N1 N 0.1885(2) 0.2471(2) 0.78279(13) 0.0491(4) Uani 1 1 d . . .
C4 C 0.2230(2) 0.3468(2) 0.70098(14) 0.0381(4) Uani 1 1 d . . .
C8 C 0.2815(2) 0.6393(2) 0.32395(15) 0.0376(4) Uani 1 1 d . . .
O1 O 0.4183(2) 0.94289(17) 0.32422(12) 0.0652(4) Uani 1 1 d . . .
C9 C 0.1867(3) 0.4671(2) 0.24202(15) 0.0420(4) Uani 1 1 d . . .
C6 C 0.3440(2) 0.6306(2) 0.65400(15) 0.0405(4) Uani 1 1 d . . .
H6 H 0.4049 0.7530 0.6818 0.049 Uiso 1 1 calc R . .
C1 C 0.2877(2) 0.5538(2) 0.52811(14) 0.0367(4) Uani 1 1 d . . .
C5 C 0.3128(3) 0.5325(2) 0.73780(15) 0.0429(4) Uani 1 1 d . . .
H5 H 0.3518 0.5898 0.8207 0.052 Uiso 1 1 calc R . .
C2 C 0.2020(3) 0.3676(2) 0.49158(16) 0.0464(5) Uani 1 1 d . . .
H2 H 0.1649 0.3106 0.4086 0.056 Uiso 1 1 calc R . .
C10 C 0.3355(3) 0.7920(2) 0.26843(16) 0.0428(4) Uani 1 1 d . . .
N2 N 0.1117(3) 0.3292(2) 0.17624(14) 0.0619(5) Uani 1 1 d . . .
C3 C 0.1715(3) 0.2676(2) 0.57418(15) 0.0468(5) Uani 1 1 d . . .
H3 H 0.1152 0.1439 0.5462 0.056 Uiso 1 1 calc R . .
C13 C 0.1053(3) 0.0538(3) 0.74285(19) 0.0585(6) Uani 1 1 d . . .
H13A H 0.0912 0.0062 0.8123 0.088 Uiso 1 1 calc R . .
H13B H 0.1873 -0.0126 0.7045 0.088 Uiso 1 1 calc R . .
H13C H -0.0178 0.0392 0.6852 0.088 Uiso 1 1 calc R . .
C12 C 0.2313(3) 0.3322(3) 0.91173(17) 0.0604(6) Uani 1 1 d . . .
H12A H 0.1974 0.2416 0.9551 0.091 Uiso 1 1 calc R . .
H12B H 0.1594 0.4305 0.9224 0.091 Uiso 1 1 calc R . .
H12C H 0.3655 0.3809 0.9434 0.091 Uiso 1 1 calc R . .
C11 C 0.3108(4) 0.8890(3) 0.08314(19) 0.0672(6) Uani 1 1 d . . .
H11A H 0.2644 0.8409 -0.0038 0.101 Uiso 1 1 calc R . .
H11B H 0.4456 0.9347 0.1048 0.101 Uiso 1 1 calc R . .
H11C H 0.2453 0.9877 0.1069 0.101 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C7 0.0421(10) 0.0333(8) 0.0400(9) 0.0098(7) 0.0116(7) 0.0034(7)
O2 0.0753(10) 0.0449(7) 0.0397(7) 0.0169(6) 0.0143(6) -0.0015(6)
N1 0.0675(11) 0.0428(8) 0.0355(8) 0.0112(7) 0.0162(7) -0.0049(7)
C4 0.0410(10) 0.0382(9) 0.0360(9) 0.0104(7) 0.0125(7) 0.0033(7)
C8 0.0399(10) 0.0333(8) 0.0392(9) 0.0094(7) 0.0107(7) 0.0031(7)
O1 0.0946(12) 0.0394(7) 0.0513(8) 0.0115(6) 0.0118(8) -0.0134(7)
C9 0.0506(11) 0.0413(10) 0.0354(9) 0.0139(8) 0.0133(8) 0.0012(8)
C6 0.0485(11) 0.0313(8) 0.0394(9) 0.0043(7) 0.0134(8) 0.0011(7)
C1 0.0386(10) 0.0353(8) 0.0371(9) 0.0083(7) 0.0132(7) 0.0035(7)
C5 0.0532(11) 0.0395(9) 0.0320(9) 0.0021(7) 0.0121(8) 0.0005(8)
C2 0.0586(12) 0.0423(10) 0.0320(9) 0.0064(8) 0.0100(8) -0.0081(8)
C10 0.0496(11) 0.0382(9) 0.0407(10) 0.0119(8) 0.0121(8) 0.0042(8)
N2 0.0877(14) 0.0477(9) 0.0411(9) 0.0064(8) 0.0142(9) -0.0116(9)
C3 0.0585(12) 0.0360(9) 0.0386(10) 0.0069(8) 0.0095(8) -0.0101(8)
C13 0.0754(15) 0.0452(11) 0.0576(12) 0.0201(10) 0.0226(11) -0.0023(10)
C12 0.0791(16) 0.0624(13) 0.0387(10) 0.0159(10) 0.0162(10) 0.0008(11)
C11 0.0940(18) 0.0590(13) 0.0528(12) 0.0290(11) 0.0211(12) 0.0011(11)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7 C8 1.352(2) . ?
C7 C1 1.438(2) . ?
C7 H7 0.9300 . ?
O2 C10 1.343(2) . ?
O2 C11 1.437(2) . ?
N1 C4 1.361(2) . ?
N1 C13 1.443(2) . ?
N1 C12 1.445(2) . ?
C4 C5 1.404(2) . ?
C4 C3 1.410(2) . ?
C8 C9 1.431(2) . ?
C8 C10 1.473(2) . ?
O1 C10 1.197(2) . ?
C9 N2 1.145(2) . ?
C6 C5 1.366(2) . ?
C6 C1 1.396(2) . ?
C6 H6 0.9300 . ?
C1 C2 1.399(2) . ?
C5 H5 0.9300 . ?
C2 C3 1.362(2) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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 C7 C1 132.04(16) . . ?
C8 C7 H7 114.0 . . ?
C1 C7 H7 114.0 . . ?
C10 O2 C11 116.09(15) . . ?
C4 N1 C13 120.85(15) . . ?
C4 N1 C12 121.09(15) . . ?
C13 N1 C12 118.06(14) . . ?
N1 C4 C5 122.15(15) . . ?
N1 C4 C3 121.44(15) . . ?
C5 C4 C3 116.41(14) . . ?
C7 C8 C9 124.43(15) . . ?
C7 C8 C10 118.55(15) . . ?
C9 C8 C10 117.02(14) . . ?
N2 C9 C8 179.6(2) . . ?
C5 C6 C1 122.44(16) . . ?
C5 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
C6 C1 C2 116.40(14) . . ?
C6 C1 C7 118.03(15) . . ?
C2 C1 C7 125.57(15) . . ?
C6 C5 C4 121.17(16) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C3 C2 C1 121.81(16) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
O1 C10 O2 122.75(16) . . ?
O1 C10 C8 125.15(16) . . ?
O2 C10 C8 112.08(15) . . ?
C2 C3 C4 121.74(16) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C13 N1 C4 C5 -176.59(17) . . . . ?
C12 N1 C4 C5 4.3(3) . . . . ?
C13 N1 C4 C3 2.8(3) . . . . ?
C12 N1 C4 C3 -176.29(17) . . . . ?
C1 C7 C8 C9 -1.0(3) . . . . ?
C1 C7 C8 C10 178.79(16) . . . . ?
C7 C8 C9 N2 -117(37) . . . . ?
C10 C8 C9 N2 63(37) . . . . ?
C5 C6 C1 C2 -1.9(2) . . . . ?
C5 C6 C1 C7 178.59(15) . . . . ?
C8 C7 C1 C6 -177.69(17) . . . . ?
C8 C7 C1 C2 2.9(3) . . . . ?
C1 C6 C5 C4 0.6(3) . . . . ?
N1 C4 C5 C6 -179.20(16) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C7 C1 C2 C3 -179.22(16) . . . . ?
C11 O2 C10 O1 -2.7(3) . . . . ?
C11 O2 C10 C8 175.77(16) . . . . ?
C7 C8 C10 O1 1.7(3) . . . . ?
C9 C8 C10 O1 -178.55(18) . . . . ?
C7 C8 C10 O2 -176.75(15) . . . . ?
C9 C8 C10 O2 3.0(2) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
N1 C4 C3 C2 178.62(17) . . . . ?
C5 C4 C3 C2 -1.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.832
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_hqdmans
_database_code_depnum_ccdc_archive 'CCDC 1044113'
_audit_update_record             
;
2015-01-17 deposited with the CCDC.
2015-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          459
_chemical_formula_moiety         CHNO
_chemical_formula_sum            'C10 H12 N2 O2'
_chemical_formula_weight         192.22

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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

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

_cell_length_a                   10.3118(10)
_cell_length_b                   7.4555(8)
_cell_length_c                   25.318(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1946.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1035
_cell_measurement_theta_min      3.3653
_cell_measurement_theta_max      29.1215

_exptl_crystal_description       cuboid
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4854
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         29.18
_reflns_number_total             2192
_reflns_number_gt                1222
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.1140P)²+1.8440P] 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         2192
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1376
_refine_ls_R_factor_gt           0.0844
_refine_ls_wR_factor_ref         0.2648
_refine_ls_wR_factor_gt          0.2121
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.8971(2) 0.2250(3) 0.67769(10) 0.0540(7) Uani 1 1 d . . .
C6 C 0.9004(3) 0.2113(3) 0.62417(11) 0.0414(7) Uani 1 1 d . . .
C3 C 0.9103(3) 0.1930(4) 0.51166(13) 0.0571(8) Uani 1 1 d . . .
C8 C 0.8193(3) 0.0969(4) 0.54049(14) 0.0603(10) Uani 1 1 d . . .
H8 H 0.7605 0.0247 0.5225 0.072 Uiso 1 1 calc R . .
C5 C 0.9942(3) 0.3048(4) 0.59410(12) 0.0492(7) Uani 1 1 d . . .
H5 H 1.0552 0.3755 0.6114 0.059 Uiso 1 1 calc R . .
C7 C 0.8130(3) 0.1046(4) 0.59522(15) 0.0554(8) Uani 1 1 d . . .
H7 H 0.7503 0.0384 0.6130 0.066 Uiso 1 1 calc R . .
C4 C 0.9970(3) 0.2936(4) 0.54038(13) 0.0543(8) Uani 1 1 d . . .
H4 H 1.0607 0.3570 0.5223 0.065 Uiso 1 1 calc R . .
C10 C 0.9966(4) 0.3217(5) 0.70649(14) 0.0724(11) Uani 1 1 d . . .
H10A H 0.9781 0.3169 0.7436 0.109 Uiso 1 1 calc R . .
H10B H 0.9980 0.4444 0.6951 0.109 Uiso 1 1 calc R . .
H10C H 1.0795 0.2677 0.6998 0.109 Uiso 1 1 calc R . .
C2 C 0.9230(4) 0.1959(5) 0.45254(18) 0.0780(12) Uani 1 1 d . . .
H2 H 0.9889 0.2669 0.4387 0.094 Uiso 1 1 calc R . .
C9 C 0.8047(4) 0.1220(6) 0.70866(16) 0.0766(11) Uani 1 1 d . . .
H9A H 0.8164 0.1483 0.7455 0.115 Uiso 1 1 calc R . .
H9B H 0.8186 -0.0037 0.7027 0.115 Uiso 1 1 calc R . .
H9C H 0.7181 0.1533 0.6982 0.115 Uiso 1 1 calc R . .
O2 O 0.9660(4) 0.2210(5) 0.34477(13) 0.1023(11) Uani 1 1 d . . .
N1 N 0.8784(4) 0.1293(6) 0.36446(12) 0.0814(11) Uani 1 1 d . . .
C1 C 0.8549(4) 0.1135(7) 0.42044(18) 0.0853(13) Uani 1 1 d . . .
H1 H 0.7879 0.0408 0.4325 0.102 Uiso 1 1 calc R . .
O1 O 0.8041(3) 0.0396(6) 0.33784(15) 0.1165(13) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0582(15) 0.0622(15) 0.0416(14) 0.0008(12) 0.0050(11) 0.0005(13)
C6 0.0424(13) 0.0412(13) 0.0407(15) -0.0017(11) -0.0001(11) 0.0058(12)
C3 0.067(2) 0.0550(17) 0.0494(19) -0.0048(14) -0.0097(15) 0.0196(16)
C8 0.0591(18) 0.0533(18) 0.068(2) -0.0180(16) -0.0296(17) 0.0104(15)
C5 0.0481(15) 0.0518(17) 0.0477(17) 0.0005(13) -0.0023(12) -0.0039(13)
C7 0.0450(15) 0.0468(16) 0.074(2) -0.0002(15) -0.0043(15) -0.0061(13)
C4 0.0622(18) 0.0562(18) 0.0447(16) 0.0048(14) -0.0006(14) 0.0050(15)
C10 0.083(2) 0.091(3) 0.0426(17) -0.0076(18) -0.0099(17) -0.004(2)
C2 0.087(3) 0.062(2) 0.085(3) -0.018(2) -0.029(2) 0.032(2)
C9 0.078(2) 0.082(2) 0.069(3) 0.017(2) 0.023(2) -0.003(2)
O2 0.126(3) 0.114(3) 0.066(2) 0.0003(18) -0.0007(19) 0.008(2)
N1 0.104(3) 0.099(3) 0.0408(17) -0.0012(18) 0.0004(18) 0.051(2)
C1 0.084(3) 0.096(3) 0.076(3) -0.009(2) -0.012(2) 0.035(2)
O1 0.111(3) 0.144(3) 0.094(3) -0.025(2) -0.025(2) 0.020(2)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
N2 C6 1.359(4) . ?
N2 C10 1.450(4) . ?
N2 C9 1.453(4) . ?
C6 C7 1.407(4) . ?
C6 C5 1.415(4) . ?
C3 C4 1.375(4) . ?
C3 C8 1.388(5) . ?
C3 C2 1.503(6) . ?
C8 C7 1.389(5) . ?
C8 H8 0.9300 . ?
C5 C4 1.363(4) . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C2 C1 1.238(6) . ?
C2 H2 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O2 N1 1.238(5) . ?
N1 O1 1.220(5) . ?
N1 C1 1.443(5) . ?
C1 H1 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
C6 N2 C10 121.4(3) . . ?
C6 N2 C9 120.9(3) . . ?
C10 N2 C9 117.1(3) . . ?
N2 C6 C7 123.1(3) . . ?
N2 C6 C5 121.1(3) . . ?
C7 C6 C5 115.8(3) . . ?
C4 C3 C8 116.3(3) . . ?
C4 C3 C2 117.5(3) . . ?
C8 C3 C2 126.2(3) . . ?
C3 C8 C7 122.3(3) . . ?
C3 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C5 C4 C3 123.2(3) . . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C2 C3 126.7(5) . . ?
C1 C2 H2 116.7 . . ?
C3 C2 H2 116.7 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 N1 O2 122.6(4) . . ?
O1 N1 C1 113.1(5) . . ?
O2 N1 C1 124.3(4) . . ?
C2 C1 N1 120.6(5) . . ?
C2 C1 H1 119.7 . . ?
N1 C1 H1 119.7 . . ?

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
C10 N2 C6 C7 173.7(3) . . . . ?
C9 N2 C6 C7 2.6(4) . . . . ?
C10 N2 C6 C5 -5.9(4) . . . . ?
C9 N2 C6 C5 -177.0(3) . . . . ?
C4 C3 C8 C7 1.7(4) . . . . ?
C2 C3 C8 C7 -178.8(3) . . . . ?
N2 C6 C5 C4 -179.2(3) . . . . ?
C7 C6 C5 C4 1.2(4) . . . . ?
C3 C8 C7 C6 -0.3(5) . . . . ?
N2 C6 C7 C8 179.2(3) . . . . ?
C5 C6 C7 C8 -1.2(4) . . . . ?
C6 C5 C4 C3 0.3(5) . . . . ?
C8 C3 C4 C5 -1.7(4) . . . . ?
C2 C3 C4 C5 178.7(3) . . . . ?
C4 C3 C2 C1 179.5(4) . . . . ?
C8 C3 C2 C1 0.0(6) . . . . ?
C3 C2 C1 N1 179.9(3) . . . . ?
O1 N1 C1 C2 179.6(4) . . . . ?
O2 N1 C1 C2 0.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.832
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_dmabmn1
_database_code_depnum_ccdc_archive 'CCDC 1044114'
_audit_update_record             
;
2015-01-17 deposited with the CCDC.
2015-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          454
_chemical_formula_moiety         CHN
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'

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

_cell_length_a                   3.9890(5)
_cell_length_b                   14.0371(12)
_cell_length_c                   9.5430(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.572(12)
_cell_angle_gamma                90.00
_cell_volume                     525.28(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    385
_cell_measurement_theta_min      3.6182
_cell_measurement_theta_max      29.0772

_exptl_crystal_description       rectangular
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             194
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2036
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0915
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.58
_diffrn_reflns_theta_max         29.14
_reflns_number_total             1665
_reflns_number_gt                946
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0000P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -9(4)
_refine_ls_number_reflns         1665
_refine_ls_number_parameters     138
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.0739
_refine_ls_wR_factor_gt          0.0539
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_restrained_S_all      0.878
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5059(9) 0.47579(19) 0.0219(3) 0.0586(8) Uani 1 1 d . . .
C2 C 0.1708(9) 0.4570(2) -0.2117(3) 0.0556(10) Uani 1 1 d . . .
H2 H 0.2228 0.3924 -0.2111 0.067 Uiso 1 1 calc R . .
C4 C -0.1220(9) 0.5921(2) -0.3376(3) 0.0482(9) Uani 1 1 d . . .
C1 C 0.3062(8) 0.5135(3) -0.0948(4) 0.0460(8) Uani 1 1 d . . .
C6 C 0.2245(8) 0.6110(2) -0.1017(3) 0.0538(9) Uani 1 1 d . . .
H6 H 0.3128 0.6504 -0.0255 0.065 Uiso 1 1 calc R . .
C5 C 0.0165(8) 0.6492(2) -0.2189(3) 0.0532(10) Uani 1 1 d . . .
H5 H -0.0343 0.7139 -0.2202 0.064 Uiso 1 1 calc R . .
C3 C -0.0392(8) 0.4961(2) -0.3278(3) 0.0551(10) Uani 1 1 d . . .
H3 H -0.1299 0.4564 -0.4033 0.066 Uiso 1 1 calc R . .
C8 C -0.4497(8) 0.7149(2) -0.5059(3) 0.0518(8) Uani 1 1 d . . .
C7 C -0.3418(7) 0.6255(2) -0.4624(3) 0.0525(9) Uani 1 1 d . . .
H7 H -0.4280 0.5776 -0.5263 0.063 Uiso 1 1 calc R . .
C11 C 0.6572(9) 0.5336(3) 0.1434(4) 0.0694(11) Uani 1 1 d . . .
H11B H 0.4822 0.5547 0.1931 0.104 Uiso 1 1 calc R . .
H11C H 0.7677 0.5879 0.1109 0.104 Uiso 1 1 calc R . .
H11A H 0.8217 0.4964 0.2066 0.104 Uiso 1 1 calc R . .
C12 C 0.5818(9) 0.3744(2) 0.0314(4) 0.0717(12) Uani 1 1 d . . .
H12B H 0.3747 0.3392 0.0297 0.107 Uiso 1 1 calc R . .
H12C H 0.7370 0.3614 0.1187 0.107 Uiso 1 1 calc R . .
H12A H 0.6839 0.3556 -0.0479 0.107 Uiso 1 1 calc R . .
N3 N -0.8472(8) 0.7337(2) -0.7472(3) 0.0750(9) Uani 1 1 d . . .
C10 C -0.3439(10) 0.8015(3) -0.4318(4) 0.0650(11) Uani 1 1 d . . .
N2 N -0.2694(9) 0.8713(2) -0.3762(4) 0.0932(13) Uani 1 1 d . . .
C9 C -0.6709(10) 0.7268(3) -0.6389(4) 0.0619(10) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.067(2) 0.0501(19) 0.057(2) 0.0006(15) 0.0062(17) 0.0052(15)
C2 0.061(2) 0.051(2) 0.053(2) -0.0040(19) 0.0076(18) 0.002(2)
C4 0.052(2) 0.044(2) 0.049(2) -0.0030(16) 0.0122(17) -0.0043(18)
C1 0.0414(19) 0.0464(18) 0.051(2) 0.0037(15) 0.0097(16) -0.0026(18)
C6 0.061(2) 0.052(2) 0.045(2) -0.0088(17) -0.0007(17) 0.001(2)
C5 0.061(3) 0.039(2) 0.057(2) 0.0021(17) 0.0060(19) -0.0015(19)
C3 0.056(2) 0.055(3) 0.053(2) -0.0085(18) 0.0053(18) -0.0095(19)
C8 0.050(2) 0.053(2) 0.0518(19) 0.0000(18) 0.0067(15) 0.000(2)
C7 0.055(2) 0.052(2) 0.050(2) -0.0014(18) 0.0076(18) -0.006(2)
C11 0.072(2) 0.074(3) 0.058(2) -0.0026(19) -0.002(2) 0.004(2)
C12 0.070(3) 0.063(3) 0.079(3) 0.015(2) 0.004(2) 0.013(2)
N3 0.080(2) 0.067(2) 0.071(2) 0.0041(19) -0.0047(18) 0.008(2)
C10 0.062(2) 0.063(3) 0.066(3) 0.004(2) 0.0014(19) -0.001(2)
N2 0.110(3) 0.068(3) 0.090(3) 0.000(2) -0.014(2) 0.000(2)
C9 0.073(3) 0.052(2) 0.062(2) 0.001(2) 0.014(2) 0.005(2)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
N1 C1 1.352(4) . ?
N1 C11 1.453(4) . ?
N1 C12 1.455(4) . ?
C2 C3 1.375(4) . ?
C2 C1 1.395(4) . ?
C2 H2 0.9300 . ?
C4 C3 1.386(4) . ?
C4 C5 1.415(4) . ?
C4 C7 1.422(4) . ?
C1 C6 1.406(4) . ?
C6 C5 1.373(3) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C8 C7 1.367(4) . ?
C8 C9 1.417(4) . ?
C8 C10 1.430(4) . ?
C7 H7 0.9300 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 H11A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H12A 0.9600 . ?
N3 C9 1.143(4) . ?
C10 N2 1.127(4) . ?

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 N1 C11 122.3(3) . . ?
C1 N1 C12 121.3(3) . . ?
C11 N1 C12 116.4(3) . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C3 C4 C5 116.3(3) . . ?
C3 C4 C7 118.7(3) . . ?
C5 C4 C7 125.0(3) . . ?
N1 C1 C2 121.2(3) . . ?
N1 C1 C6 121.1(3) . . ?
C2 C1 C6 117.6(3) . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C2 C3 C4 123.1(3) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 C10 125.6(3) . . ?
C9 C8 C10 114.9(4) . . ?
C8 C7 C4 132.0(3) . . ?
C8 C7 H7 114.0 . . ?
C4 C7 H7 114.0 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
H11B C11 H11A 109.5 . . ?
H11C C11 H11A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?
H12C C12 H12A 109.5 . . ?
N2 C10 C8 177.7(5) . . ?
N3 C9 C8 178.0(4) . . ?

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
C11 N1 C1 C2 178.4(3) . . . . ?
C12 N1 C1 C2 -1.3(5) . . . . ?
C11 N1 C1 C6 -2.4(5) . . . . ?
C12 N1 C1 C6 177.9(4) . . . . ?
C3 C2 C1 N1 178.3(3) . . . . ?
C3 C2 C1 C6 -1.0(5) . . . . ?
N1 C1 C6 C5 -178.7(3) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
C1 C6 C5 C4 -0.4(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C7 C4 C5 C6 179.3(3) . . . . ?
C1 C2 C3 C4 1.4(5) . . . . ?
C5 C4 C3 C2 -1.3(5) . . . . ?
C7 C4 C3 C2 -180.0(3) . . . . ?
C9 C8 C7 C4 179.4(3) . . . . ?
C10 C8 C7 C4 3.2(6) . . . . ?
C3 C4 C7 C8 -175.4(3) . . . . ?
C5 C4 C7 C8 6.1(6) . . . . ?
C7 C8 C10 N2 -165(12) . . . . ?
C9 C8 C10 N2 19(12) . . . . ?
C7 C8 C9 N3 -14(12) . . . . ?
C10 C8 C9 N3 163(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.799
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.100
_refine_diff_density_min         -0.099
_refine_diff_density_rms         0.023
