# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2013


data_global

data_exp_14064
#TrackingRef 'web_deposit_cif_file_0_MinjieLi_1344393218.wy-01-31-01.cif'

_audit_creation_method           'Created with Diamond (www.crystalimpact.com)'
_audit_creation_date             12-05-14
_audit_update_record             12-05-14
_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_weight         308.330
_refine_ls_R_factor_all          0.067
_cell_length_a                   16.289(5)
_cell_length_b                   5.772(5)
_cell_length_c                   16.527(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 92.596(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1552.3(15)
_cell_formula_units_Z            4
_symmetry_int_tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  -P_2yn

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 'x, y, z'
2 '0.500-x, 0.500+y, 0.500-z'
3 '-x, -y, -z'
4 '0.500+x, 0.500-y, 0.500+z'

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
C ? 1.200
H ? 1.200
O ? 1.200
N ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
C1 C 0.8456(1) 0.0321(4) 0.1451(1) 1.000 4 e ? d Uani 0.0496(5)
H1 H 0.7922 0.0730 0.1566 1.000 4 e ? calc Uiso 0.06000
C2 C 0.8602(1) -0.1154(4) 0.0817(1) 1.000 4 e ? d Uani 0.0596(6)
H2 H 0.8162 -0.1725 0.0498 1.000 4 e ? calc Uiso 0.07200
C3 C 0.9392(2) -0.1793(5) 0.0651(1) 1.000 4 e ? d Uani 0.0650(6)
H3 H 0.9476 -0.2824 0.0230 1.000 4 e ? calc Uiso 0.07800
C4 C 1.0066(1) -0.0924(4) 0.1101(1) 1.000 4 e ? d Uani 0.0589(6)
H4 H 1.0599 -0.1355 0.0990 1.000 4 e ? calc Uiso 0.07100
C5 C 0.9911(1) 0.0603(3) 0.1717(1) 1.000 4 e ? d Uani 0.0428(5)
C6 C 0.9116(1) 0.1181(3) 0.1912(1) 1.000 4 e ? d Uani 0.0394(4)
C7 C 0.9176(1) 0.2781(3) 0.2633(1) 1.000 4 e ? d Uani 0.0379(4)
C8 C 0.8703(1) 0.5043(4) 0.2509(2) 1.000 4 e ? d Uani 0.0582(6)
H8A H 0.8767 0.5975 0.2989 1.000 4 e ? calc Uiso 0.08700
H8B H 0.8131 0.4710 0.2401 1.000 4 e ? calc Uiso 0.08700
H8C H 0.8914 0.5868 0.2058 1.000 4 e ? calc Uiso 0.08700
C9 C 0.8904(1) 0.1544(4) 0.3401(1) 1.000 4 e ? d Uani 0.0525(5)
H9A H 0.8945 0.2595 0.3851 1.000 4 e ? calc Uiso 0.07900
H9B H 0.9252 0.0229 0.3511 1.000 4 e ? calc Uiso 0.07900
H9C H 0.8345 0.1037 0.3320 1.000 4 e ? calc Uiso 0.07900
C10 C 1.0103(1) 0.3143(3) 0.2703(1) 1.000 4 e ? d Uani 0.0391(4)
C11 C 1.0488(1) 0.4843(3) 0.3241(1) 1.000 4 e ? d Uani 0.0426(5)
H11 H 1.0174 0.5518 0.3634 1.000 4 e ? calc Uiso 0.05100
C12 C 1.1270(1) 0.5486(4) 0.3200(1) 1.000 4 e ? d Uani 0.0449(5)
H12 H 1.1580 0.4651 0.2842 1.000 4 e ? calc Uiso 0.05400
C13 C 1.1703(1) 0.7337(3) 0.3647(1) 1.000 4 e ? d Uani 0.0401(4)
C14 C 1.2553(1) 0.7598(3) 0.3546(1) 1.000 4 e ? d Uani 0.0415(5)
C15 C 1.2984(1) 0.9433(4) 0.3927(1) 1.000 4 e ? d Uani 0.0478(5)
H15 H 1.3543 0.9607 0.3854 1.000 4 e ? calc Uiso 0.05700
C16 C 1.2585(1) 1.0979(4) 0.4408(1) 1.000 4 e ? d Uani 0.0477(5)
H16 H 1.2870 1.2194 0.4662 1.000 4 e ? calc Uiso 0.05700
C17 C 1.1753(1) 1.0686(3) 0.4505(1) 1.000 4 e ? d Uani 0.0417(5)
C18 C 1.1312(1) 0.8907(3) 0.4136(1) 1.000 4 e ? d Uani 0.0415(5)
H18 H 1.0753 0.8759 0.4216 1.000 4 e ? calc Uiso 0.05000
O1 O 1.0583(1) 1.2191(3) 0.5045(1) 1.000 4 e ? d Uani 0.0638(5)
O2 O 1.1735(1) 1.3809(4) 0.5377(1) 1.000 4 e ? d Uani 0.0825(6)
O3 O 1.2919(1) 0.6057(2) 0.3076(1) 1.000 4 e ? d Uani 0.0540(4)
H3A H 1.3408 0.6377 0.3056 1.000 4 e ? calc Uiso 0.08100
N2 N 1.1327(1) 1.2334(3) 0.5007(1) 1.000 4 e ? d Uani 0.0500(5)
N3 N 1.0501(1) 0.1848(3) 0.2208(1) 1.000 4 e ? d Uani 0.0447(4)



loop_
_geom_bond_atom_site_symbol_1
_geom_bond_atom_site_symbol_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . . 1.379(3) no
C1 C6 . . 1.381(3) no
C1 H1 . . 0.9300 no
C2 C3 . . 1.378(4) no
C2 H2 . . 0.9300 no
C3 C4 . . 1.391(3) no
C3 H3 . . 0.9300 no
C4 C5 . . 1.379(3) no
C4 H4 . . 0.9300 no
C5 C6 . . 1.389(2) no
C5 N3 . . 1.423(2) no
C6 C7 . . 1.508(3) no
C7 C10 . . 1.524(2) no
C7 C8 . . 1.525(3) no
C7 C9 . . 1.538(3) no
C8 H8A . . 0.9600 no
C8 H8B . . 0.9600 no
C8 H8C . . 0.9600 no
C9 H9A . . 0.9600 no
C9 H9B . . 0.9600 no
C9 H9C . . 0.9600 no
C10 N3 . . 1.303(2) no
C10 C11 . . 1.448(3) no
C11 C12 . . 1.331(3) no
C11 H11 . . 0.9300 no
C12 C13 . . 1.462(3) no
C12 H12 . . 0.9300 no
C13 C18 . . 1.389(3) no
C13 C14 . . 1.411(2) no
C14 O3 . . 1.337(2) no
C14 C15 . . 1.404(3) no
C15 C16 . . 1.377(3) no
C15 H15 . . 0.9300 no
C16 C17 . . 1.383(3) no
C16 H16 . . 0.9300 no
C17 C18 . . 1.379(3) no
C17 N2 . . 1.459(3) no
C18 H18 . . 0.9300 no
O1 N2 . . 1.217(2) no
O2 N2 . . 1.226(2) no
O3 H3A . . 0.8200 no

loop_
_geom_angle_atom_site_symbol_1
_geom_angle_atom_site_symbol_2
_geom_angle_atom_site_symbol_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . . 118.99(19) no
C2 C1 H1 . . . 120.50 no
C6 C1 H1 . . . 120.50 no
C3 C2 C1 . . . 120.8(2) no
C3 C2 H2 . . . 119.60 no
C1 C2 H2 . . . 119.60 no
C2 C3 C4 . . . 121.2(2) no
C2 C3 H3 . . . 119.40 no
C4 C3 H3 . . . 119.40 no
C5 C4 C3 . . . 117.3(2) no
C5 C4 H4 . . . 121.30 no
C3 C4 H4 . . . 121.30 no
C4 C5 C6 . . . 121.86(18) no
C4 C5 N3 . . . 127.04(17) no
C6 C5 N3 . . . 111.05(16) no
C1 C6 C5 . . . 119.76(18) no
C1 C6 C7 . . . 132.63(16) no
C5 C6 C7 . . . 107.60(15) no
C6 C7 C10 . . . 99.92(13) no
C6 C7 C8 . . . 113.80(17) no
C10 C7 C8 . . . 112.66(16) no
C6 C7 C9 . . . 110.93(16) no
C10 C7 C9 . . . 108.83(15) no
C8 C7 C9 . . . 110.25(16) no
C7 C8 H8A . . . 109.50 no
C7 C8 H8B . . . 109.50 no
H8A C8 H8B . . . 109.50 no
C7 C8 H8C . . . 109.50 no
H8A C8 H8C . . . 109.50 no
H8B C8 H8C . . . 109.50 no
C7 C9 H9A . . . 109.50 no
C7 C9 H9B . . . 109.50 no
H9A C9 H9B . . . 109.50 no
C7 C9 H9C . . . 109.50 no
H9A C9 H9C . . . 109.50 no
H9B C9 H9C . . . 109.50 no
N3 C10 C11 . . . 124.11(15) no
N3 C10 C7 . . . 113.14(16) no
C11 C10 C7 . . . 122.68(15) no
C12 C11 C10 . . . 123.17(17) no
C12 C11 H11 . . . 118.40 no
C10 C11 H11 . . . 118.40 no
C11 C12 C13 . . . 128.28(18) no
C11 C12 H12 . . . 115.90 no
C13 C12 H12 . . . 115.90 no
C18 C13 C14 . . . 118.53(17) no
C18 C13 C12 . . . 123.19(15) no
C14 C13 C12 . . . 118.21(17) no
O3 C14 C15 . . . 122.36(16) no
O3 C14 C13 . . . 117.55(17) no
C15 C14 C13 . . . 120.09(17) no
C16 C15 C14 . . . 120.56(17) no
C16 C15 H15 . . . 119.70 no
C14 C15 H15 . . . 119.70 no
C15 C16 C17 . . . 118.56(18) no
C15 C16 H16 . . . 120.70 no
C17 C16 H16 . . . 120.70 no
C18 C17 C16 . . . 122.30(18) no
C18 C17 N2 . . . 118.96(16) no
C16 C17 N2 . . . 118.74(17) no
C17 C18 C13 . . . 119.96(16) no
C17 C18 H18 . . . 120.00 no
C13 C18 H18 . . . 120.00 no
C14 O3 H3A . . . 109.50 no
O1 N2 O2 . . . 122.59(18) no
O1 N2 C17 . . . 119.07(17) no
O2 N2 C17 . . . 118.34(17) no
C10 N3 C5 . . . 107.82(14) no

data_global

# Attachment 'web_deposit_cif_file_1_MinjieLi_1344393218.wy-01-34-02.CIF'


data_wy-2
#TrackingRef 'web_deposit_cif_file_1_MinjieLi_1344393218.wy-01-34-02.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N O'
_chemical_formula_weight         263.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   5.9589(12)
_cell_length_b                   20.362(4)
_cell_length_c                   12.149(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.17(3)
_cell_angle_gamma                90.00
_cell_volume                     1473.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_T_max  0.9866
_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            10953
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2568
_reflns_number_gt                1654
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1378P)²+0.1121P] 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         2568
_refine_ls_number_parameters     194
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.2310
_refine_ls_wR_factor_gt          0.1985
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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 0.8388(5) 0.19643(14) 0.0971(2) 0.0605(7) Uani 1 1 d . A .
C2 C 1.0131(5) 0.15324(15) 0.0817(3) 0.0671(8) Uani 1 1 d . . .
H2 H 1.0399 0.1379 0.0112 0.081 Uiso 1 1 calc R . .
C3 C 1.1480(5) 0.13261(17) 0.1695(3) 0.0750(9) Uani 1 1 d . . .
H3 H 1.2650 0.1035 0.1577 0.090 Uiso 1 1 calc R . .
C4 C 1.1126(6) 0.15410(19) 0.2730(3) 0.0825(10) Uani 1 1 d . . .
H4 H 1.2041 0.1398 0.3320 0.099 Uiso 1 1 calc R . .
C5 C 0.9416(6) 0.19690(17) 0.2898(2) 0.0742(9) Uani 1 1 d . A .
H5 H 0.9203 0.2119 0.3610 0.089 Uiso 1 1 calc R . .
C6 C 0.7964(5) 0.21925(13) 0.2045(2) 0.0615(7) Uani 1 1 d . . .
C7 C 0.6204(5) 0.26449(17) 0.2341(3) 0.0769(9) Uani 1 1 d . A 1
H7 H 0.6091 0.2720 0.3092 0.092 Uiso 1 1 calc R A 1
C8 C 0.4804(6) 0.29506(17) 0.1726(3) 0.0607(12) Uani 0.843(8) 1 d P A 1
H8 H 0.4813 0.2876 0.0971 0.073 Uiso 0.843(8) 1 calc PR A 1
C9 C 0.3118(5) 0.34310(14) 0.2155(3) 0.0639(8) Uani 1 1 d . A 1
C8' C 0.468(2) 0.2968(6) 0.2571(13) 0.038(5) Uani 0.157(8) 1 d PU A 2
H8' H 0.4385 0.2892 0.3306 0.045 Uiso 0.157(8) 1 d PR A 3
C10 C 0.2145(4) 0.39388(14) 0.1380(2) 0.0575(7) Uani 1 1 d . . .
C11 C 0.0733(4) 0.43296(13) 0.2132(2) 0.0533(7) Uani 1 1 d . A .
C12 C 0.0841(5) 0.40220(15) 0.3161(2) 0.0616(7) Uani 1 1 d . . .
C13 C -0.0342(6) 0.4225(2) 0.4020(3) 0.0904(11) Uani 1 1 d . A .
H13 H -0.0251 0.4005 0.4691 0.108 Uiso 1 1 calc R . .
C14 C -0.1661(7) 0.4757(3) 0.3875(4) 0.1067(14) Uani 1 1 d . . .
H14 H -0.2518 0.4897 0.4454 0.128 Uiso 1 1 calc R A .
C15 C -0.1790(7) 0.5109(2) 0.2882(5) 0.1103(16) Uani 1 1 d . A .
H15 H -0.2667 0.5486 0.2817 0.132 Uiso 1 1 calc R . .
C16 C -0.0560(6) 0.48817(16) 0.1975(3) 0.0807(10) Uani 1 1 d . . .
H16 H -0.0630 0.5099 0.1301 0.097 Uiso 1 1 calc R A .
C17 C 0.3970(6) 0.4352(2) 0.0866(3) 0.0906(11) Uani 1 1 d . A .
H17A H 0.3289 0.4709 0.0459 0.136 Uiso 1 1 calc R . .
H17B H 0.4808 0.4083 0.0379 0.136 Uiso 1 1 calc R . .
H17C H 0.4961 0.4524 0.1437 0.136 Uiso 1 1 calc R . .
C18 C 0.0661(5) 0.36049(18) 0.0473(2) 0.0776(9) Uani 1 1 d . A .
H18A H -0.0472 0.3345 0.0807 0.116 Uiso 1 1 calc R . .
H18B H 0.1576 0.3327 0.0035 0.116 Uiso 1 1 calc R . .
H18C H -0.0042 0.3935 0.0012 0.116 Uiso 1 1 calc R . .
N1 N 0.2381(4) 0.34768(12) 0.3136(2) 0.0707(7) Uani 1 1 d . A .
O1 O 0.7074(4) 0.21881(11) 0.01177(18) 0.0837(7) Uani 1 1 d . . .
H1 H 0.7460 0.2016 -0.0455 0.125 Uiso 1 1 calc R A .


_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 O1 1.354(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.416(4) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.452(4) . ?
C7 C8 1.263(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.509(5) . ?
C8 H8 0.9300 . ?
C9 N1 1.290(4) . ?
C9 C10 1.500(4) . ?
C8' H8' 0.9300 . ?
C10 C11 1.495(4) . ?
C10 C17 1.527(4) . ?
C10 C18 1.544(4) . ?
C11 C16 1.372(4) . ?
C11 C12 1.397(4) . ?
C12 C13 1.347(4) . ?
C12 N1 1.441(4) . ?
C13 C14 1.347(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.402(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.424(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O1 H1 0.8200 . ?

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
O1 C1 C2 121.8(3) . . ?
O1 C1 C6 118.5(2) . . ?
C2 C1 C6 119.8(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 122.8(3) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C5 C6 C1 116.6(3) . . ?
C5 C6 C7 117.0(3) . . ?
C1 C6 C7 126.4(3) . . ?
C8 C7 C6 129.3(3) . . ?
C8 C7 H7 115.4 . . ?
C6 C7 H7 115.4 . . ?
C7 C8 C9 123.3(3) . . ?
C7 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
N1 C9 C10 113.2(3) . . ?
N1 C9 C8 128.4(3) . . ?
C10 C9 C8 118.5(3) . . ?
C11 C10 C9 101.3(2) . . ?
C11 C10 C17 112.5(3) . . ?
C9 C10 C17 111.8(2) . . ?
C11 C10 C18 110.5(2) . . ?
C9 C10 C18 110.0(2) . . ?
C17 C10 C18 110.4(3) . . ?
C16 C11 C12 119.9(3) . . ?
C16 C11 C10 132.6(3) . . ?
C12 C11 C10 107.5(2) . . ?
C13 C12 C11 123.3(3) . . ?
C13 C12 N1 127.2(3) . . ?
C11 C12 N1 109.6(2) . . ?
C12 C13 C14 117.7(4) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C13 C14 C15 122.5(4) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C14 C15 C16 119.1(4) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C15 117.5(4) . . ?
C11 C16 H16 121.3 . . ?
C15 C16 H16 121.3 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 N1 C12 108.3(2) . . ?
C1 O1 H1 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.82 1.98 2.774(3) 161.9 4_665

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.049

data_global

# Attachment 'web_deposit_cif_file_2_MinjieLi_1344393218.wy-01-46-01.cif'

data_120415-wx01-kwq
#TrackingRef 'web_deposit_cif_file_2_MinjieLi_1344393218.wy-01-46-01.cif'

_audit_creation_method           'Created with Diamond (www.crystalimpact.com)'
_audit_creation_date             12-05-14
_audit_update_record             12-05-14
_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_weight         308.330
_refine_ls_R_factor_all          0.070
_cell_length_a                   8.578(5)
_cell_length_b                   17.638(5)
_cell_length_c                   10.333(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 102.223(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1527.9(12)
_cell_formula_units_Z            4
_symmetry_int_tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  -P_2ybc

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 'x, y, z'
2 '-x, 0.500+y, 0.500-z'
3 '-x, -y, -z'
4 'x, 0.500-y, 0.500+z'

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
O ? 1.200
H ? 1.200
N ? 1.200
C ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
O1 O 0.5520(1) 0.0892(1) 0.5219(1) 1.000 4 e ? d Uani 0.0474(3)
H1A H 0.4551 0.0839 0.5106 1.000 4 e ? calc Uiso 0.07100
N1 N 1.2948(1) 0.1201(1) 0.6684(1) 1.000 4 e ? d Uani 0.0412(3)
O2 O 0.2682(1) 0.0761(1) 0.3669(1) 1.000 4 e ? d Uani 0.0811(5)
N2 N 0.3241(2) 0.0577(1) 0.2729(1) 1.000 4 e ? d Uani 0.0532(4)
O3 O 0.2411(2) 0.0354(1) 0.1701(1) 1.000 4 e ? d Uani 0.0919(6)
C7 C 1.1444(2) 0.1286(1) 0.6695(1) 1.000 4 e ? d Uani 0.0391(3)
C18 C 0.5971(2) 0.0796(1) 0.4064(1) 1.000 4 e ? d Uani 0.0370(3)
C11 C 1.0276(2) 0.1019(1) 0.5568(2) 1.000 4 e ? d Uani 0.0425(4)
H11 H 1.0685 0.0775 0.4915 1.000 4 e ? calc Uiso 0.05100
C14 C 0.8158(2) 0.0726(1) 0.2943(2) 1.000 4 e ? d Uani 0.0456(4)
H14 H 0.9245 0.0759 0.2966 1.000 4 e ? calc Uiso 0.05500
C8 C 1.1133(2) 0.1698(1) 0.7921(2) 1.000 4 e ? d Uani 0.0451(4)
C13 C 0.7619(2) 0.0854(1) 0.4101(1) 1.000 4 e ? d Uani 0.0383(3)
C12 C 0.8695(2) 0.1076(1) 0.5340(2) 1.000 4 e ? d Uani 0.0423(4)
H12 H 0.8242 0.1269 0.6013 1.000 4 e ? calc Uiso 0.05100
C6 C 1.3830(2) 0.1531(1) 0.7864(2) 1.000 4 e ? d Uani 0.0400(4)
C15 C 0.7132(2) 0.0553(1) 0.1756(2) 1.000 4 e ? d Uani 0.0518(4)
H15 H 0.7529 0.0467 0.0998 1.000 4 e ? calc Uiso 0.06200
C17 C 0.4956(2) 0.0629(1) 0.2846(2) 1.000 4 e ? d Uani 0.0415(4)
C4 C 1.3489(2) 0.2193(1) 0.9804(2) 1.000 4 e ? d Uani 0.0620(5)
H4 H 1.2836 0.2394 1.0331 1.000 4 e ? calc Uiso 0.07400
C2 C 1.6109(2) 0.1945(1) 0.9414(2) 1.000 4 e ? d Uani 0.0565(5)
H2 H 1.7210 0.1990 0.9689 1.000 4 e ? calc Uiso 0.06800
C5 C 1.2841(2) 0.1834(1) 0.8628(2) 1.000 4 e ? d Uani 0.0457(4)
C16 C 0.5528(2) 0.0509(1) 0.1708(2) 1.000 4 e ? d Uani 0.0494(4)
H16 H 0.4826 0.0398 0.0914 1.000 4 e ? calc Uiso 0.05900
C1 C 1.5477(2) 0.1576(1) 0.8246(2) 1.000 4 e ? d Uani 0.0483(4)
H1 H 1.6132 0.1364 0.7731 1.000 4 e ? calc Uiso 0.05800
C9 C 1.0250(2) 0.1191(1) 0.8745(2) 1.000 4 e ? d Uani 0.0609(5)
H9A H 0.9171 0.1115 0.8273 1.000 4 e ? calc Uiso 0.09100
H9B H 1.0248 0.1432 0.9578 1.000 4 e ? calc Uiso 0.09100
H9C H 1.0781 0.0710 0.8899 1.000 4 e ? calc Uiso 0.09100
C10 C 1.0251(2) 0.2453(1) 0.7581(2) 1.000 4 e ? d Uani 0.0666(5)
H10A H 0.9170 0.2355 0.7133 1.000 4 e ? calc Uiso 0.10000
H10B H 1.0776 0.2745 0.7016 1.000 4 e ? calc Uiso 0.10000
H10C H 1.0255 0.2730 0.8381 1.000 4 e ? calc Uiso 0.10000
C3 C 1.5133(2) 0.2249(1) 1.0182(2) 1.000 4 e ? d Uani 0.0643(5)
H3 H 1.5586 0.2497 1.0966 1.000 4 e ? calc Uiso 0.07700




