# 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_sm1
_database_code_depnum_ccdc_archive 'CCDC 1025252'
_audit_update_record             
;
2014-09-20 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 N2 O2'
_chemical_formula_weight         354.39

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                   8.2226(7)
_cell_length_b                   9.7911(7)
_cell_length_c                   12.1078(9)
_cell_angle_alpha                85.263(3)
_cell_angle_beta                 72.053(3)
_cell_angle_gamma                75.796(3)
_cell_volume                     898.97(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1450
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      20.37

_exptl_crystal_description       Triclinic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            13318
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0858
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         33.01
_reflns_number_total             5675
_reflns_number_gt                2194
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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 > 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)+(0.1427P)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         5675
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1936
_refine_ls_R_factor_gt           0.0784
_refine_ls_wR_factor_ref         0.2841
_refine_ls_wR_factor_gt          0.2248
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_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 1.1105(3) 0.11911(19) 0.79378(18) 0.0749(6) Uani 1 1 d . . .
H1 H 1.1038 0.0738 0.8544 0.112 Uiso 1 1 calc R . .
O2 O 0.6839(4) 0.3544(2) 1.1762(2) 0.0982(8) Uani 1 1 d . . .
N1 N 0.8153(3) 0.6803(2) 0.89720(17) 0.0508(6) Uani 1 1 d . . .
N2 N 0.8139(3) 0.0920(3) 1.0428(2) 0.0741(7) Uani 1 1 d . . .
C1 C 0.6167(6) 1.0373(4) 0.6033(3) 0.0928(12) Uani 1 1 d . . .
H1A H 0.5614 1.0890 0.5516 0.111 Uiso 1 1 calc R . .
C2 C 0.7739(6) 1.0588(4) 0.6077(3) 0.0944(12) Uani 1 1 d . . .
H2 H 0.8258 1.1243 0.5583 0.113 Uiso 1 1 calc R . .
C3 C 0.8534(4) 0.9840(3) 0.6848(3) 0.0698(8) Uani 1 1 d . . .
H3 H 0.9596 0.9992 0.6872 0.084 Uiso 1 1 calc R . .
C4 C 0.7790(3) 0.8859(2) 0.7595(2) 0.0524(7) Uani 1 1 d . . .
C5 C 0.8701(4) 0.8093(3) 0.8453(2) 0.0535(7) Uani 1 1 d . . .
H5A H 0.9956 0.7848 0.8064 0.064 Uiso 1 1 calc R . .
H5B H 0.8501 0.8736 0.9074 0.064 Uiso 1 1 calc R . .
C6 C 0.8980(3) 0.5458(2) 0.8567(2) 0.0450(6) Uani 1 1 d . . .
C7 C 0.8377(3) 0.4508(2) 0.9419(2) 0.0454(6) Uani 1 1 d . . .
C8 C 0.9056(3) 0.3029(2) 0.9209(2) 0.0453(6) Uani 1 1 d . . .
C9 C 0.8450(3) 0.1935(3) 0.9963(2) 0.0550(7) Uani 1 1 d . . .
C10 C 1.0329(3) 0.2571(3) 0.8186(2) 0.0549(7) Uani 1 1 d . . .
C11 C 1.0194(3) 0.4996(3) 0.7429(2) 0.0536(7) Uani 1 1 d . . .
C12 C 1.0705(4) 0.5882(3) 0.6491(3) 0.0780(10) Uani 1 1 d . . .
H12 H 1.0262 0.6850 0.6573 0.094 Uiso 1 1 calc R . .
C13 C 1.1840(5) 0.5360(4) 0.5456(3) 0.1127(16) Uani 1 1 d . . .
H13 H 1.2154 0.5973 0.4842 0.135 Uiso 1 1 calc R . .
C14 C 1.2546(5) 0.3894(4) 0.5307(3) 0.1100(15) Uani 1 1 d . . .
H14 H 1.3339 0.3536 0.4606 0.132 Uiso 1 1 calc R . .
C15 C 1.2039(5) 0.3022(3) 0.6211(3) 0.0824(10) Uani 1 1 d . . .
H15 H 1.2480 0.2055 0.6120 0.099 Uiso 1 1 calc R . .
C16 C 1.0873(3) 0.3543(3) 0.7277(2) 0.0575(7) Uani 1 1 d . . .
C17 C 0.6996(3) 0.6731(3) 1.0047(2) 0.0486(6) Uani 1 1 d . . .
C18 C 0.5901(4) 0.8039(3) 1.0673(3) 0.0658(8) Uani 1 1 d . . .
H18A H 0.6232 0.8118 1.1355 0.099 Uiso 1 1 calc R . .
H18B H 0.4685 0.8007 1.0894 0.099 Uiso 1 1 calc R . .
H18C H 0.6077 0.8839 1.0175 0.099 Uiso 1 1 calc R . .
C19 C 0.7105(3) 0.5321(3) 1.0374(2) 0.0458(6) Uani 1 1 d . . .
C20 C 0.6206(4) 0.4764(3) 1.1495(2) 0.0602(7) Uani 1 1 d . . .
C21 C 0.4670(4) 0.5625(4) 1.2334(3) 0.0878(11) Uani 1 1 d . . .
H21A H 0.4010 0.5020 1.2848 0.132 Uiso 1 1 calc R . .
H21B H 0.3941 0.6237 1.1925 0.132 Uiso 1 1 calc R . .
H21C H 0.5058 0.6179 1.2777 0.132 Uiso 1 1 calc R . .
C22 C 0.5428(4) 0.9402(4) 0.6749(3) 0.0816(10) Uani 1 1 d . . .
H22 H 0.4374 0.9247 0.6712 0.098 Uiso 1 1 calc R . .
C23 C 0.6229(4) 0.8641(3) 0.7532(2) 0.0615(7) Uani 1 1 d . . .
H23 H 0.5710 0.7980 0.8019 0.074 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 C10 1.359(3) . ?
O1 H1 0.8200 . ?
O2 C20 1.240(3) . ?
N1 C17 1.364(3) . ?
N1 C6 1.378(3) . ?
N1 C5 1.472(3) . ?
N2 C9 1.147(3) . ?
C1 C22 1.359(5) . ?
C1 C2 1.377(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.365(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C23 1.378(4) . ?
C4 C5 1.509(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.388(3) . ?
C6 C11 1.461(4) . ?
C7 C8 1.432(3) . ?
C7 C19 1.436(3) . ?
C8 C10 1.376(4) . ?
C8 C9 1.432(4) . ?
C10 C16 1.432(4) . ?
C11 C12 1.393(4) . ?
C11 C16 1.400(4) . ?
C12 C13 1.361(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.414(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.356(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(4) . ?
C15 H15 0.9300 . ?
C17 C19 1.393(3) . ?
C17 C18 1.482(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.465(4) . ?
C20 C21 1.472(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.384(4) . ?
C22 H22 0.9300 . ?
C23 H23 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
C10 O1 H1 109.5 . . ?
C17 N1 C6 109.2(2) . . ?
C17 N1 C5 124.4(2) . . ?
C6 N1 C5 125.1(2) . . ?
C22 C1 C2 119.7(3) . . ?
C22 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C23 C4 C3 118.2(3) . . ?
C23 C4 C5 122.8(2) . . ?
C3 C4 C5 119.0(3) . . ?
N1 C5 C4 115.8(2) . . ?
N1 C5 H5A 108.3 . . ?
C4 C5 H5A 108.3 . . ?
N1 C5 H5B 108.3 . . ?
C4 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
N1 C6 C7 108.4(2) . . ?
N1 C6 C11 129.5(2) . . ?
C7 C6 C11 122.0(2) . . ?
C6 C7 C8 119.1(2) . . ?
C6 C7 C19 107.0(2) . . ?
C8 C7 C19 133.9(2) . . ?
C10 C8 C7 119.8(2) . . ?
C10 C8 C9 115.0(2) . . ?
C7 C8 C9 125.1(2) . . ?
N2 C9 C8 169.2(3) . . ?
O1 C10 C8 123.7(2) . . ?
O1 C10 C16 115.2(2) . . ?
C8 C10 C16 121.1(2) . . ?
C12 C11 C16 118.0(2) . . ?
C12 C11 C6 125.3(2) . . ?
C16 C11 C6 116.7(2) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 118.4(3) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C16 121.6(3) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C11 120.0(3) . . ?
C15 C16 C10 119.1(3) . . ?
C11 C16 C10 120.8(2) . . ?
N1 C17 C19 108.9(2) . . ?
N1 C17 C18 120.3(2) . . ?
C19 C17 C18 130.8(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 C7 106.4(2) . . ?
C17 C19 C20 127.3(2) . . ?
C7 C19 C20 126.1(2) . . ?
O2 C20 C19 117.9(3) . . ?
O2 C20 C21 119.5(3) . . ?
C19 C20 C21 122.5(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 C22 C23 120.6(3) . . ?
C1 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C4 C23 C22 120.3(3) . . ?
C4 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.837
_diffrn_reflns_theta_full        33.01
_diffrn_measured_fraction_theta_full 0.837
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_sm3
_database_code_depnum_ccdc_archive 'CCDC 1025253'
_audit_update_record             
;
2014-09-20 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N2 O2'
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.4136(7)
_cell_length_b                   9.9725(7)
_cell_length_c                   10.1281(13)
_cell_angle_alpha                111.742(3)
_cell_angle_beta                 96.696(3)
_cell_angle_gamma                116.846(2)
_cell_volume                     740.30(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3295
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      29.34

_exptl_crystal_description       Triclinic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            10092
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         30.38
_reflns_number_total             3771
_reflns_number_gt                2784
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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 > 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)+(0.0813P)²+0.1160P] 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         3771
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.046
_refine_ls_shift/su_mean         0.005

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 0.79572(17) 1.16730(16) 0.50862(13) 0.0531(3) Uani 1 1 d . . .
O2 O 1.16864(14) 1.34637(14) 1.03923(12) 0.0445(3) Uani 1 1 d . . .
H2 H 1.1231 1.3998 1.0397 0.067 Uiso 1 1 calc R . .
N1 N 0.9038(2) 1.3946(2) 0.83766(17) 0.0686(5) Uani 1 1 d . . .
N2 N 0.82263(15) 0.72836(15) 0.51339(13) 0.0320(3) Uani 1 1 d . . .
C1 C 0.7103(2) 1.0112(2) 0.44861(17) 0.0365(3) Uani 1 1 d . . .
C2 C 0.76773(17) 0.92231(18) 0.50471(16) 0.0308(3) Uani 1 1 d . . .
C3 C 0.88893(17) 0.99764(17) 0.65076(15) 0.0289(3) Uani 1 1 d . . .
C4 C 0.92391(17) 0.87616(18) 0.65231(15) 0.0295(3) Uani 1 1 d . . .
C5 C 1.05074(17) 0.91291(18) 0.77636(16) 0.0298(3) Uani 1 1 d . . .
C6 C 1.1069(2) 0.8041(2) 0.77939(18) 0.0384(4) Uani 1 1 d . . .
H6 H 1.0597 0.6981 0.6948 0.046 Uiso 1 1 calc R . .
C7 C 1.2291(2) 0.8512(2) 0.90391(19) 0.0430(4) Uani 1 1 d . . .
H7 H 1.2624 0.7762 0.9032 0.052 Uiso 1 1 calc R . .
C8 C 1.3046(2) 1.0103(2) 1.03193(19) 0.0449(4) Uani 1 1 d . . .
H8 H 1.3865 1.0406 1.1166 0.054 Uiso 1 1 calc R . .
C9 C 0.5473(2) 0.9145(3) 0.3197(2) 0.0569(5) Uani 1 1 d . . .
H9A H 0.5028 0.9859 0.3284 0.085 Uiso 1 1 calc R . .
H9B H 0.4670 0.8138 0.3225 0.085 Uiso 1 1 calc R . .
H9C H 0.5680 0.8821 0.2256 0.085 Uiso 1 1 calc R . .
C10 C 0.96858(17) 1.15982(18) 0.78427(16) 0.0306(3) Uani 1 1 d . . .
C11 C 0.9278(2) 1.2859(2) 0.80326(17) 0.0412(4) Uani 1 1 d . . .
C12 C 1.08545(18) 1.19660(18) 0.90905(16) 0.0319(3) Uani 1 1 d . . .
C13 C 1.13155(17) 1.07702(18) 0.90562(15) 0.0305(3) Uani 1 1 d . . .
C14 C 1.25754(19) 1.1212(2) 1.03210(17) 0.0392(4) Uani 1 1 d . . .
H14 H 1.3093 1.2279 1.1170 0.047 Uiso 1 1 calc R . .
C15 C 0.80604(19) 0.56548(19) 0.47190(17) 0.0376(4) Uani 1 1 d . . .
H15 H 0.8890 0.5492 0.4297 0.045 Uiso 1 1 calc R . .
C16 C 0.7477(2) 0.4835(2) 0.5683(2) 0.0483(4) Uani 1 1 d . . .
H16A H 0.7964 0.4214 0.5854 0.058 Uiso 1 1 calc R . .
H16B H 0.7226 0.5427 0.6532 0.058 Uiso 1 1 calc R . .
C17 C 0.6317(2) 0.4091(2) 0.4132(2) 0.0509(4) Uani 1 1 d . . .
H17A H 0.5363 0.4234 0.4040 0.061 Uiso 1 1 calc R . .
H17B H 0.6101 0.3020 0.3361 0.061 Uiso 1 1 calc R . .
C18 C 0.73192(18) 0.75711(19) 0.42327(16) 0.0327(3) Uani 1 1 d . . .
C19 C 0.6281(2) 0.6277(2) 0.26130(17) 0.0439(4) Uani 1 1 d . . .
H19A H 0.6648 0.5492 0.2275 0.066 Uiso 1 1 calc R . .
H19B H 0.6420 0.6845 0.2009 0.066 Uiso 1 1 calc R . .
H19C H 0.5109 0.5660 0.2514 0.066 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 C1 1.223(2) . ?
O2 C12 1.3514(17) . ?
O2 H2 0.8200 . ?
N1 C11 1.143(2) . ?
N2 C18 1.3703(18) . ?
N2 C4 1.3938(17) . ?
N2 C15 1.4455(18) . ?
C1 C2 1.461(2) . ?
C1 C9 1.501(2) . ?
C2 C18 1.391(2) . ?
C2 C3 1.4364(19) . ?
C3 C4 1.3963(18) . ?
C3 C10 1.4333(19) . ?
C4 C5 1.4325(19) . ?
C5 C6 1.413(2) . ?
C5 C13 1.424(2) . ?
C6 C7 1.368(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.395(2) . ?
C7 H7 0.9300 . ?
C8 C14 1.364(2) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C12 1.3820(19) . ?
C10 C11 1.428(2) . ?
C12 C13 1.433(2) . ?
C13 C14 1.413(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.495(2) . ?
C15 C17 1.501(2) . ?
C15 H15 0.9800 . ?
C16 C17 1.488(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.493(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C12 O2 H2 109.5 . . ?
C18 N2 C4 109.59(11) . . ?
C18 N2 C15 124.36(12) . . ?
C4 N2 C15 125.94(12) . . ?
O1 C1 C2 119.44(14) . . ?
O1 C1 C9 119.29(15) . . ?
C2 C1 C9 121.27(15) . . ?
C18 C2 C3 106.84(12) . . ?
C18 C2 C1 127.13(14) . . ?
C3 C2 C1 125.66(13) . . ?
C4 C3 C10 119.23(12) . . ?
C4 C3 C2 107.46(12) . . ?
C10 C3 C2 133.27(12) . . ?
N2 C4 C3 107.34(11) . . ?
N2 C4 C5 129.92(12) . . ?
C3 C4 C5 122.64(13) . . ?
C6 C5 C13 117.44(13) . . ?
C6 C5 C4 125.96(13) . . ?
C13 C5 C4 116.55(12) . . ?
C7 C6 C5 121.49(15) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 120.79(14) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C14 C8 C7 119.61(14) . . ?
C14 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C10 C11 115.89(13) . . ?
C12 C10 C3 119.47(12) . . ?
C11 C10 C3 124.50(12) . . ?
N1 C11 C10 171.33(17) . . ?
O2 C12 C10 123.88(13) . . ?
O2 C12 C13 115.06(12) . . ?
C10 C12 C13 121.02(13) . . ?
C14 C13 C5 119.41(13) . . ?
C14 C13 C12 119.87(13) . . ?
C5 C13 C12 120.72(12) . . ?
C8 C14 C13 121.20(15) . . ?
C8 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
N2 C15 C16 117.40(13) . . ?
N2 C15 C17 118.44(13) . . ?
C16 C15 C17 59.58(11) . . ?
N2 C15 H15 116.5 . . ?
C16 C15 H15 116.5 . . ?
C17 C15 H15 116.5 . . ?
C17 C16 C15 60.42(11) . . ?
C17 C16 H16A 117.7 . . ?
C15 C16 H16A 117.7 . . ?
C17 C16 H16B 117.7 . . ?
C15 C16 H16B 117.7 . . ?
H16A C16 H16B 114.9 . . ?
C16 C17 C15 60.00(11) . . ?
C16 C17 H17A 117.8 . . ?
C15 C17 H17A 117.8 . . ?
C16 C17 H17B 117.8 . . ?
C15 C17 H17B 117.8 . . ?
H17A C17 H17B 114.9 . . ?
N2 C18 C2 108.69(13) . . ?
N2 C18 C19 121.22(13) . . ?
C2 C18 C19 129.87(14) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.841
_diffrn_reflns_theta_full        30.38
_diffrn_measured_fraction_theta_full 0.841
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.099
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 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_sm1
_database_code_depnum_ccdc_archive 'CCDC 1025342'
_audit_update_record             
;
2014-09-20 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 Cl N3 O2'
_chemical_formula_weight         405.87

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   10.0940(18)
_cell_length_b                   11.275(2)
_cell_length_c                   17.835(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2029.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    899
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      16.47

_exptl_crystal_description       Orthorhombic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            9835
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0951
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         26.64
_reflns_number_total             3788
_reflns_number_gt                2302
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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 > 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)+(0.0765P)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   -0.04(11)
_refine_ls_number_reflns         3788
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_restrained_S_all      0.893
_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
Cl1 Cl -0.07385(14) -0.27075(11) -0.03185(8) 0.0783(5) Uani 1 1 d . . .
O1 O 0.5962(3) 0.2980(3) 0.13115(18) 0.0625(9) Uani 1 1 d . . .
O2 O 0.5730(3) 0.2228(2) -0.04216(15) 0.0481(7) Uani 1 1 d . . .
N1 N 0.2196(3) 0.1176(3) 0.20767(18) 0.0391(8) Uani 1 1 d . . .
C26 C -0.2841(5) 0.0277(6) 0.3442(3) 0.097(2) Uani 1 1 d . . .
H38 H -0.2950 -0.0554 0.3542 0.146 Uiso 1 1 calc R . .
H39 H -0.3546 0.0545 0.3123 0.146 Uiso 1 1 calc R . .
H37 H -0.2862 0.0710 0.3905 0.146 Uiso 1 1 calc R . .
N3 N 0.3710(4) 0.2860(4) -0.0066(2) 0.0511(10) Uani 1 1 d . . .
H34 H 0.381(5) 0.342(4) -0.036(3) 0.077 Uiso 1 1 d . . .
H35 H 0.300(5) 0.278(5) 0.024(2) 0.077 Uiso 1 1 d . . .
C1 C 0.0286(4) -0.1710(4) 0.0152(3) 0.0467(11) Uani 1 1 d . . .
C2 C 0.0744(4) -0.0710(4) -0.0199(2) 0.0458(11) Uani 1 1 d . . .
H2 H 0.0541 -0.0572 -0.0700 0.055 Uiso 1 1 calc R . .
C3 C 0.1503(4) 0.0088(3) 0.0193(2) 0.0396(10) Uani 1 1 d . . .
H3 H 0.1812 0.0766 -0.0047 0.048 Uiso 1 1 calc R . .
C4 C 0.1819(4) -0.0103(3) 0.0945(2) 0.0358(9) Uani 1 1 d . . .
C5 C 0.2601(4) 0.0783(4) 0.1373(2) 0.0357(9) Uani 1 1 d . . .
C6 C 0.0920(4) 0.0922(3) 0.2413(2) 0.0362(9) Uani 1 1 d . . .
C7 C -0.0197(4) 0.1433(4) 0.2116(2) 0.0494(11) Uani 1 1 d . . .
H7 H -0.0132 0.1927 0.1700 0.059 Uiso 1 1 calc R . .
C8 C -0.1416(4) 0.1212(5) 0.2437(3) 0.0574(13) Uani 1 1 d . . .
H8 H -0.2171 0.1558 0.2234 0.069 Uiso 1 1 calc R . .
C9 C -0.1527(5) 0.0480(4) 0.3057(3) 0.0570(13) Uani 1 1 d . . .
C10 C 0.1358(4) -0.1135(3) 0.1286(2) 0.0414(10) Uani 1 1 d . . .
H10 H 0.1575 -0.1289 0.1784 0.050 Uiso 1 1 calc R . .
C11 C 0.0581(4) -0.1938(4) 0.0894(2) 0.0456(11) Uani 1 1 d . . .
H40 H 0.0264 -0.2619 0.1127 0.055 Uiso 1 1 calc R . .
C12 C 0.3084(4) 0.1979(4) 0.2359(2) 0.0416(10) Uani 1 1 d . . .
C13 C 0.4093(4) 0.2090(3) 0.1839(2) 0.0380(9) Uani 1 1 d . . .
C14 C 0.5242(4) 0.2884(4) 0.1857(2) 0.0458(10) Uani 1 1 d . . .
C15 C 0.5567(5) 0.3598(5) 0.2547(3) 0.0717(15) Uani 1 1 d . . .
H32 H 0.6355 0.4054 0.2459 0.107 Uiso 1 1 calc R . .
H31 H 0.5709 0.3072 0.2963 0.107 Uiso 1 1 calc R . .
H30 H 0.4845 0.4123 0.2659 0.107 Uiso 1 1 calc R . .
C16 C 0.3786(4) 0.1329(3) 0.1222(2) 0.0353(9) Uani 1 1 d . . .
C17 C 0.4597(4) 0.1096(4) 0.0527(2) 0.0399(10) Uani 1 1 d . . .
H17 H 0.4127 0.0474 0.0251 0.048 Uiso 1 1 calc R . .
C18 C 0.4750(4) 0.2147(3) -0.0024(2) 0.0374(9) Uani 1 1 d . . .
C19 C 0.5908(5) 0.0613(4) 0.0701(2) 0.0490(11) Uani 1 1 d . . .
N5 N 0.6901(5) 0.0196(4) 0.0834(3) 0.0757(13) Uani 1 1 d . . .
C21 C 0.2793(4) 0.2603(5) 0.3088(2) 0.0621(14) Uani 1 1 d . . .
H21A H 0.2244 0.2107 0.3396 0.093 Uiso 1 1 calc R . .
H21B H 0.2340 0.3335 0.2988 0.093 Uiso 1 1 calc R . .
H21C H 0.3609 0.2766 0.3345 0.093 Uiso 1 1 calc R . .
C22 C 0.0830(4) 0.0179(4) 0.3014(2) 0.0513(11) Uani 1 1 d . . .
H22 H 0.1587 -0.0176 0.3209 0.062 Uiso 1 1 calc R . .
C23 C -0.0389(5) -0.0041(4) 0.3330(3) 0.0609(14) Uani 1 1 d . . .
H23 H -0.0447 -0.0552 0.3738 0.073 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
Cl1 C1 1.743(4) . ?
O1 C14 1.220(5) . ?
O2 C18 1.221(4) . ?
N1 C12 1.370(5) . ?
N1 C5 1.392(5) . ?
N1 C6 1.449(5) . ?
C26 C9 1.511(6) . ?
C26 H38 0.9600 . ?
C26 H39 0.9600 . ?
C26 H37 0.9600 . ?
N3 C18 1.325(5) . ?
N3 H34 0.83(5) . ?
N3 H35 0.90(5) . ?
C1 C2 1.369(6) . ?
C1 C11 1.382(6) . ?
C2 C3 1.373(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(5) . ?
C3 H3 0.9300 . ?
C4 C10 1.393(5) . ?
C4 C5 1.484(5) . ?
C5 C16 1.372(5) . ?
C6 C22 1.364(5) . ?
C6 C7 1.372(5) . ?
C7 C8 1.380(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(7) . ?
C8 H8 0.9300 . ?
C9 C23 1.379(6) . ?
C10 C11 1.387(5) . ?
C10 H10 0.9300 . ?
C11 H40 0.9300 . ?
C12 C13 1.383(5) . ?
C12 C21 1.507(6) . ?
C13 C16 1.430(5) . ?
C13 C14 1.466(5) . ?
C14 C15 1.507(6) . ?
C15 H32 0.9600 . ?
C15 H31 0.9600 . ?
C15 H30 0.9600 . ?
C16 C17 1.507(5) . ?
C17 C19 1.464(6) . ?
C17 C18 1.546(5) . ?
C17 H17 0.9800 . ?
C19 N5 1.133(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.376(6) . ?
C22 H22 0.9300 . ?
C23 H23 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
C12 N1 C5 110.5(3) . . ?
C12 N1 C6 124.0(3) . . ?
C5 N1 C6 124.8(3) . . ?
C9 C26 H38 109.5 . . ?
C9 C26 H39 109.5 . . ?
H38 C26 H39 109.5 . . ?
C9 C26 H37 109.5 . . ?
H38 C26 H37 109.5 . . ?
H39 C26 H37 109.5 . . ?
C18 N3 H34 114(4) . . ?
C18 N3 H35 122(3) . . ?
H34 N3 H35 124(5) . . ?
C2 C1 C11 121.2(4) . . ?
C2 C1 Cl1 120.8(3) . . ?
C11 C1 Cl1 118.0(3) . . ?
C1 C2 C3 119.7(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C10 C4 C3 118.1(4) . . ?
C10 C4 C5 121.1(3) . . ?
C3 C4 C5 120.8(3) . . ?
C16 C5 N1 106.9(3) . . ?
C16 C5 C4 131.7(4) . . ?
N1 C5 C4 121.4(3) . . ?
C22 C6 C7 120.4(4) . . ?
C22 C6 N1 120.4(4) . . ?
C7 C6 N1 119.2(3) . . ?
C6 C7 C8 119.8(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C9 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C23 C9 C8 117.9(4) . . ?
C23 C9 C26 120.4(5) . . ?
C8 C9 C26 121.7(5) . . ?
C11 C10 C4 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C4 C10 H10 119.5 . . ?
C1 C11 C10 118.9(4) . . ?
C1 C11 H40 120.5 . . ?
C10 C11 H40 120.5 . . ?
N1 C12 C13 107.2(3) . . ?
N1 C12 C21 119.9(3) . . ?
C13 C12 C21 132.8(4) . . ?
C12 C13 C16 107.6(3) . . ?
C12 C13 C14 128.6(4) . . ?
C16 C13 C14 123.7(4) . . ?
O1 C14 C13 120.5(4) . . ?
O1 C14 C15 118.3(4) . . ?
C13 C14 C15 121.1(4) . . ?
C14 C15 H32 109.5 . . ?
C14 C15 H31 109.5 . . ?
H32 C15 H31 109.5 . . ?
C14 C15 H30 109.5 . . ?
H32 C15 H30 109.5 . . ?
H31 C15 H30 109.5 . . ?
C5 C16 C13 107.9(3) . . ?
C5 C16 C17 123.8(3) . . ?
C13 C16 C17 128.3(3) . . ?
C19 C17 C16 112.4(3) . . ?
C19 C17 C18 109.2(3) . . ?
C16 C17 C18 116.3(3) . . ?
C19 C17 H17 106.0 . . ?
C16 C17 H17 106.0 . . ?
C18 C17 H17 106.0 . . ?
O2 C18 N3 124.3(4) . . ?
O2 C18 C17 120.5(4) . . ?
N3 C18 C17 115.0(3) . . ?
N5 C19 C17 177.4(5) . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C6 C22 C23 119.5(4) . . ?
C6 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C9 121.6(4) . . ?
C22 C23 H23 119.2 . . ?
C9 C23 H23 119.2 . . ?

_diffrn_measured_fraction_theta_max 0.925
_diffrn_reflns_theta_full        26.64
_diffrn_measured_fraction_theta_full 0.925
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_sm1
_audit_block_doi                 10.5517/cc13zvmk
_database_code_depnum_ccdc_archive 'CCDC 1042549'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O3'
_chemical_formula_weight         372.41

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   Pbca

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

_cell_length_a                   13.1520(11)
_cell_length_b                   14.8788(12)
_cell_length_c                   19.1290(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3743.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       colourless
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            48593
_diffrn_reflns_av_R_equivalents  0.1101
_diffrn_reflns_av_sigmaI/netI    0.0901
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         30.12
_reflns_number_total             5444
_reflns_number_gt                2533
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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 > 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)+(0.1013P)²+0.8584P] 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         5444
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1683
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.2082
_refine_ls_wR_factor_gt          0.1674
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_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 0.44103(13) 0.04321(12) 0.66224(8) 0.0517(5) Uani 1 1 d . . .
O2 O 0.4312(3) 0.0160(2) 0.77362(11) 0.1610(18) Uani 1 1 d . . .
O3 O 0.63657(14) 0.13133(12) 0.99378(8) 0.0544(5) Uani 1 1 d . . .
H3 H 0.5985 0.0882 0.9989 0.082 Uiso 1 1 calc R . .
N1 N 0.68505(14) 0.20956(12) 0.71458(9) 0.0400(5) Uani 1 1 d . . .
C30 C 0.50827(18) 0.05425(15) 0.89834(11) 0.0387(5) Uani 1 1 d . . .
C1 C 0.3440(2) -0.0228(2) 0.57196(14) 0.0688(9) Uani 1 1 d . . .
H1A H 0.3378 0.0362 0.5522 0.103 Uiso 1 1 calc R . .
H1B H 0.2841 -0.0571 0.5614 0.103 Uiso 1 1 calc R . .
H1C H 0.4024 -0.0523 0.5524 0.103 Uiso 1 1 calc R . .
C2 C 0.3560(2) -0.0157(2) 0.64896(14) 0.0617(8) Uani 1 1 d . . .
H2A H 0.2947 0.0086 0.6698 0.074 Uiso 1 1 calc R . .
H2B H 0.3687 -0.0745 0.6690 0.074 Uiso 1 1 calc R . .
C3 C 0.4725(2) 0.05327(18) 0.72715(13) 0.0552(7) Uani 1 1 d . . .
C4 C 0.55781(18) 0.11365(15) 0.73601(11) 0.0403(6) Uani 1 1 d . . .
C5 C 0.60473(17) 0.13682(14) 0.80152(11) 0.0359(5) Uani 1 1 d . . .
C6 C 0.68320(17) 0.19710(15) 0.78693(11) 0.0371(5) Uani 1 1 d . . .
C7 C 0.74775(18) 0.23595(15) 0.83877(11) 0.0393(5) Uani 1 1 d . . .
C8 C 0.82969(19) 0.29604(17) 0.82676(13) 0.0501(6) Uani 1 1 d . . .
H8 H 0.8438 0.3151 0.7815 0.060 Uiso 1 1 calc R . .
C9 C 0.8880(2) 0.32616(18) 0.88083(14) 0.0562(7) Uani 1 1 d . . .
H9 H 0.9422 0.3645 0.8715 0.067 Uiso 1 1 calc R . .
C10 C 0.8686(2) 0.30097(19) 0.94946(14) 0.0571(7) Uani 1 1 d . . .
H10 H 0.9088 0.3228 0.9857 0.069 Uiso 1 1 calc R . .
C11 C 0.60942(18) 0.15957(15) 0.68406(11) 0.0397(5) Uani 1 1 d . . .
C12 C 0.72838(17) 0.21006(15) 0.90915(11) 0.0398(5) Uani 1 1 d . . .
C13 C 0.64769(17) 0.14882(15) 0.92500(11) 0.0386(5) Uani 1 1 d . . .
C14 C 0.58696(16) 0.11255(15) 0.87338(11) 0.0365(5) Uani 1 1 d . . .
N4 N 0.45148(17) 0.01194(15) 0.92766(10) 0.0577(6) Uani 1 1 d . . .
H15 H 0.4081 -0.0204 0.9500 0.069 Uiso 1 1 calc R . .
C16 C 0.79034(19) 0.24429(17) 0.96312(12) 0.0496(6) Uani 1 1 d . . .
H16 H 0.7772 0.2276 1.0091 0.060 Uiso 1 1 calc R . .
C17 C 0.75024(17) 0.27105(15) 0.67766(10) 0.0374(5) Uani 1 1 d . . .
C18 C 0.84481(19) 0.24303(17) 0.65592(12) 0.0469(6) Uani 1 1 d . . .
H18 H 0.8648 0.1836 0.6619 0.056 Uiso 1 1 calc R . .
C19 C 0.90953(19) 0.3045(2) 0.62517(14) 0.0554(7) Uani 1 1 d . . .
H19 H 0.9741 0.2868 0.6109 0.067 Uiso 1 1 calc R . .
C20 C 0.8787(2) 0.3916(2) 0.61563(15) 0.0618(8) Uani 1 1 d . . .
H20 H 0.9226 0.4329 0.5952 0.074 Uiso 1 1 calc R . .
C21 C 0.7832(2) 0.41820(17) 0.63606(14) 0.0583(7) Uani 1 1 d . . .
H21 H 0.7623 0.4771 0.6285 0.070 Uiso 1 1 calc R . .
C22 C 0.71876(19) 0.35807(16) 0.66756(12) 0.0462(6) Uani 1 1 d . . .
H22 H 0.6544 0.3761 0.6819 0.055 Uiso 1 1 calc R . .
C23 C 0.5965(2) 0.16166(17) 0.60673(12) 0.0513(7) Uani 1 1 d . . .
H23A H 0.6057 0.2220 0.5901 0.077 Uiso 1 1 calc R . .
H23B H 0.5294 0.1413 0.5948 0.077 Uiso 1 1 calc R . .
H23C H 0.6460 0.1230 0.5853 0.077 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 C3 1.317(3) . ?
O1 C2 1.443(3) . ?
O2 C3 1.180(3) . ?
O3 C13 1.349(3) . ?
O3 H3 0.8200 . ?
N1 C11 1.372(3) . ?
N1 C6 1.397(3) . ?
N1 C17 1.439(3) . ?
C30 N4 1.126(3) . ?
C30 C14 1.432(3) . ?
C1 C2 1.485(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.447(3) . ?
C4 C11 1.384(3) . ?
C4 C5 1.439(3) . ?
C5 C6 1.395(3) . ?
C5 C14 1.440(3) . ?
C6 C7 1.428(3) . ?
C7 C12 1.423(3) . ?
C7 C8 1.419(3) . ?
C8 C9 1.363(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(4) . ?
C9 H9 0.9300 . ?
C10 C16 1.356(4) . ?
C10 H10 0.9300 . ?
C11 C23 1.489(3) . ?
C12 C16 1.411(3) . ?
C12 C13 1.431(3) . ?
C13 C14 1.380(3) . ?
N4 H15 0.8600 . ?
C16 H16 0.9300 . ?
C17 C22 1.373(3) . ?
C17 C18 1.376(3) . ?
C18 C19 1.381(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.370(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.373(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C3 O1 C2 118.57(19) . . ?
C13 O3 H3 109.5 . . ?
C11 N1 C6 109.70(18) . . ?
C11 N1 C17 124.58(18) . . ?
C6 N1 C17 125.52(18) . . ?
N4 C30 C14 169.6(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 107.5(2) . . ?
O1 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 O1 120.8(2) . . ?
O2 C3 C4 124.1(2) . . ?
O1 C3 C4 115.1(2) . . ?
C11 C4 C5 107.3(2) . . ?
C11 C4 C3 127.1(2) . . ?
C5 C4 C3 125.7(2) . . ?
C6 C5 C14 118.17(19) . . ?
C6 C5 C4 107.27(18) . . ?
C14 C5 C4 134.6(2) . . ?
N1 C6 C5 107.25(18) . . ?
N1 C6 C7 128.6(2) . . ?
C5 C6 C7 124.12(19) . . ?
C12 C7 C8 117.4(2) . . ?
C12 C7 C6 116.2(2) . . ?
C8 C7 C6 126.5(2) . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.7(3) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C16 C10 C9 119.3(2) . . ?
C16 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N1 C11 C4 108.52(19) . . ?
N1 C11 C23 119.6(2) . . ?
C4 C11 C23 131.9(2) . . ?
C16 C12 C7 119.4(2) . . ?
C16 C12 C13 120.2(2) . . ?
C7 C12 C13 120.4(2) . . ?
O3 C13 C14 124.0(2) . . ?
O3 C13 C12 114.19(19) . . ?
C14 C13 C12 121.8(2) . . ?
C13 C14 C5 119.4(2) . . ?
C13 C14 C30 114.61(19) . . ?
C5 C14 C30 125.96(19) . . ?
C30 N4 H15 180.0 . . ?
C10 C16 C12 121.5(2) . . ?
C10 C16 H16 119.3 . . ?
C12 C16 H16 119.3 . . ?
C22 C17 C18 121.0(2) . . ?
C22 C17 N1 119.3(2) . . ?
C18 C17 N1 119.6(2) . . ?
C19 C18 C17 119.0(2) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 119.4(2) . . ?
C21 C22 H22 120.3 . . ?
C17 C22 H22 120.3 . . ?
C11 C23 H23A 109.5 . . ?
C11 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C11 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        30.12
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.050
