# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_RJ-4
_database_code_depnum_ccdc_archive 'CCDC 1031108'
_audit_update_record             
;
2014-10-27 deposited with the CCDC.
2016-02-10 downloaded from the CCDC.
;
_audit_creation_date             2014-09-04
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_formula_moiety         'C19 H17 N3 O3'
_chemical_formula_sum            'C19 H17 N3 O3'
_chemical_formula_weight         335.37
_chemical_oxdiff_formula         C19H19N3O3
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_cell_length_a                   8.6467(4)
_cell_length_b                   11.5046(5)
_cell_length_c                   17.1290(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.114(4)
_cell_angle_gamma                90
_cell_volume                     1702.79(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1386
_cell_measurement_temperature    291.7(3)
_cell_measurement_theta_max      27.3480
_cell_measurement_theta_min      3.7290
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3081
_exptl_crystal_F_000             704.3449
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7748
_diffrn_reflns_theta_full        28.595997
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         3.21
_diffrn_ambient_temperature      291.7(3)
_diffrn_detector_area_resol_mean 16.1279
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.8915
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -9.00   88.00   1.0000   18.9500
omega____ theta____ kappa____ phi______ frames
    -       22.4059   77.0000  -30.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega  -43.00    2.00   1.0000   18.9500
omega____ theta____ kappa____ phi______ frames
    -       22.4059   19.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega   62.00   88.00   1.0000   18.9500
omega____ theta____ kappa____ phi______ frames
    -       22.4059   19.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega    9.00   93.00   1.0000   18.9500
omega____ theta____ kappa____ phi______ frames
    -       22.4059   57.0000 -120.0000 84
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0095018000
_diffrn_orient_matrix_UB_12      0.0116072000
_diffrn_orient_matrix_UB_13      -0.0402086000
_diffrn_orient_matrix_UB_21      0.0245199000
_diffrn_orient_matrix_UB_22      -0.0581738000
_diffrn_orient_matrix_UB_23      -0.0055920000
_diffrn_orient_matrix_UB_31      -0.0777149000
_diffrn_orient_matrix_UB_32      -0.0169095000
_diffrn_orient_matrix_UB_33      -0.0083249000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              -9
_reflns_number_gt                2449
_reflns_number_total             3886
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.399265
_refine_diff_density_min         -0.394583
_refine_diff_density_rms         0.085888
_refine_ls_d_res_high            0.742462
_refine_ls_d_res_low             6.342301
_refine_ls_goodness_of_fit_ref   1.044343
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3886
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.103700
_refine_ls_R_factor_gt           0.057903
_refine_ls_restrained_S_all      1.044343
_refine_ls_shift/su_max          0.0015
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+0.3693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.136652
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.49691(16) 0.50417(12) 0.39125(9) 0.0385(4) Uani 1.000000 .
O20 O 0.34607(17) 0.89774(13) 0.39036(9) 0.0461(4) Uani 1.000000 .
O19 O 0.48296(18) 0.77478(14) 0.55869(8) 0.0462(4) Uani 1.000000 .
N11 N 0.6489(2) 0.90562(16) 0.50685(11) 0.0452(5) Uani 1.000000 .
N23 N 0.7154(2) 0.42460(15) 0.43615(11) 0.0465(5) Uani 1.000000 .
N22 N 0.9566(2) 0.6499(2) 0.51038(15) 0.0716(7) Uani 1.000000 .
C6 C 0.3207(2) 0.79620(18) 0.37242(11) 0.0335(5) Uani 1.000000 .
C4 C 0.1756(2) 0.65198(19) 0.28417(12) 0.0382(5) Uani 1.000000 .
C8 C 0.5906(2) 0.74274(17) 0.42814(11) 0.0300(5) Uani 1.000000 .
C10 C 0.6386(2) 0.52557(18) 0.42689(11) 0.0336(5) Uani 1.000000 .
C2 C 0.4025(2) 0.59668(18) 0.37253(11) 0.0319(5) Uani 1.000000 .
C7 C 0.4382(2) 0.70651(17) 0.38953(11) 0.0296(5) Uani 1.000000 .
C12 C 0.5636(2) 0.80771(18) 0.50667(12) 0.0347(5) Uani 1.000000 .
C9 C 0.6863(2) 0.63386(18) 0.44516(12) 0.0332(5) Uani 1.000000 .
C18 C 0.7162(2) 0.92525(19) 0.43433(15) 0.0439(6) Uani 1.000000 .
C13 C 0.6807(2) 0.83313(19) 0.38434(13) 0.0368(5) Uani 1.000000 .
C21 C 0.8358(3) 0.64509(19) 0.48178(14) 0.0435(6) Uani 1.000000 .
C5 C 0.1676(2) 0.75884(19) 0.33668(13) 0.0410(6) Uani 1.000000 .
C3 C 0.2572(2) 0.55592(19) 0.33181(13) 0.0418(6) Uani 1.000000 .
C14 C 0.7302(3) 0.8341(2) 0.30934(14) 0.0499(6) Uani 1.000000 .
C15 C 0.8166(3) 0.9280(3) 0.28507(19) 0.0696(9) Uani 1.000000 .
C25 C 0.0133(3) 0.6104(2) 0.25909(16) 0.0561(7) Uani 1.000000 .
C24 C 0.2652(3) 0.6812(2) 0.21135(13) 0.0557(7) Uani 1.000000 .
C17 C 0.8024(3) 1.0186(2) 0.4116(2) 0.0652(8) Uani 1.000000 .
C16 C 0.8520(3) 1.0175(3) 0.3355(2) 0.0787(10) Uani 1.000000 .
H14 H 0.7064(3) 0.7730(2) 0.27541(14) 0.0599(8) Uiso 1.000000 R
H15 H 0.8507(3) 0.9303(3) 0.23424(19) 0.0836(10) Uiso 1.000000 R
H16 H 0.9109(3) 1.0793(3) 0.3181(2) 0.0945(12) Uiso 1.000000 R
H17 H 0.8265(3) 1.0797(2) 0.4455(2) 0.0782(10) Uiso 1.000000 R
H11 H 0.6609(2) 0.95088(16) 0.54657(11) 0.0543(6) Uiso 1.000000 R
H5a H 0.0977(2) 0.74251(19) 0.37829(13) 0.0492(7) Uiso 1.000000 R
H5b H 0.1242(2) 0.82287(19) 0.30625(13) 0.0492(7) Uiso 1.000000 R
H3a H 0.1874(2) 0.52669(19) 0.37026(13) 0.0502(7) Uiso 1.000000 R
H3b H 0.2814(2) 0.49218(19) 0.29726(13) 0.0502(7) Uiso 1.000000 R
H25a H -0.0449(7) 0.5948(14) 0.30459(16) 0.0842(11) Uiso 1.000000 G
H25b H -0.0381(8) 0.6696(7) 0.2283(9) 0.0842(11) Uiso 1.000000 G
H25c H 0.0209(3) 0.5407(9) 0.2286(9) 0.0842(11) Uiso 1.000000 G
H24a H 0.2071(9) 0.7359(11) 0.1798(5) 0.0835(10) Uiso 1.000000 G
H24b H 0.3635(8) 0.7144(13) 0.22673(13) 0.0835(10) Uiso 1.000000 G
H24c H 0.2812(16) 0.6115(3) 0.1818(5) 0.0835(10) Uiso 1.000000 G
H23a H 0.7821(13) 0.4323(5) 0.4743(7) 0.0557(6) Uiso 1.000000 G
H23b H 0.6518(3) 0.3698(3) 0.4466(10) 0.0557(6) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C10 1.371(2) .
O1 C2 1.372(2) .
O20 C6 1.226(2) .
O19 C12 1.212(2) .
N11 C12 1.346(3) .
N11 C18 1.409(3) .
N11 H11 0.8600 .
N23 C10 1.345(3) .
N23 H23a 0.8600 .
N23 H23b 0.8600 .
N22 C21 1.138(3) .
C6 C7 1.470(3) .
C6 C5 1.501(3) .
C4 C5 1.526(3) .
C4 C3 1.530(3) .
C4 C25 1.530(3) .
C4 C24 1.529(3) .
C8 C7 1.511(3) .
C8 C12 1.564(3) .
C8 C9 1.523(3) .
C8 C13 1.515(3) .
C10 C9 1.346(3) .
C2 C7 1.331(3) .
C2 C3 1.490(3) .
C9 C21 1.422(3) .
C18 C13 1.390(3) .
C18 C17 1.373(3) .
C13 C14 1.369(3) .
C5 H5a 0.9700 .
C5 H5b 0.9700 .
C3 H3a 0.9700 .
C3 H3b 0.9700 .
C14 C15 1.386(4) .
C14 H14 0.9300 .
C15 C16 1.371(4) .
C15 H15 0.9300 .
C25 H25a 0.9600 .
C25 H25b 0.9600 .
C25 H25c 0.9600 .
C24 H24a 0.9600 .
C24 H24b 0.9600 .
C24 H24c 0.9600 .
C17 C16 1.387(5) .
C17 H17 0.9300 .
C16 H16 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
C2 O1 C10 118.63(16) . .
C18 N11 C12 112.09(18) . .
H11 N11 C12 123.96(13) . .
H11 N11 C18 123.96(12) . .
H23a N23 C10 108.40(12) . .
H23b N23 C10 109.89(12) . .
H23b N23 H23a 109.5 . .
C7 C6 O20 120.19(18) . .
C5 C6 O20 121.49(18) . .
C5 C6 C7 118.24(18) . .
C3 C4 C5 107.30(16) . .
C25 C4 C5 110.87(18) . .
C25 C4 C3 108.90(19) . .
C24 C4 C5 109.82(19) . .
C24 C4 C3 110.86(19) . .
C24 C4 C25 109.07(18) . .
C12 C8 C7 110.64(16) . .
C9 C8 C7 108.39(16) . .
C9 C8 C12 109.01(16) . .
C13 C8 C7 115.39(16) . .
C13 C8 C12 101.18(16) . .
C13 C8 C9 111.95(16) . .
N23 C10 O1 109.08(18) . .
C9 C10 O1 122.08(18) . .
C9 C10 N23 128.79(18) . .
C7 C2 O1 123.63(17) . .
C3 C2 O1 110.46(17) . .
C3 C2 C7 125.91(18) . .
C8 C7 C6 118.61(17) . .
C2 C7 C6 118.00(17) . .
C2 C7 C8 123.35(17) . .
N11 C12 O19 126.1(2) . .
C8 C12 O19 126.24(19) . .
C8 C12 N11 107.60(19) . .
C10 C9 C8 123.87(17) . .
C21 C9 C8 119.22(18) . .
C21 C9 C10 116.91(19) . .
C13 C18 N11 109.40(19) . .
C17 C18 N11 128.5(2) . .
C17 C18 C13 122.1(3) . .
C18 C13 C8 108.91(19) . .
C14 C13 C8 130.9(2) . .
C14 C13 C18 120.2(2) . .
C9 C21 N22 177.5(3) . .
C4 C5 C6 114.37(17) . .
H5a C5 C6 108.67(12) . .
H5a C5 C4 108.67(12) . .
H5b C5 C6 108.67(12) . .
H5b C5 C4 108.67(11) . .
H5b C5 H5a 107.6 . .
C2 C3 C4 112.73(18) . .
H3a C3 C4 109.04(12) . .
H3a C3 C2 109.04(12) . .
H3b C3 C4 109.04(11) . .
H3b C3 C2 109.04(12) . .
H3b C3 H3a 107.8 . .
C15 C14 C13 118.6(3) . .
H14 C14 C13 120.71(15) . .
H14 C14 C15 120.71(19) . .
C16 C15 C14 120.4(3) . .
H15 C15 C14 119.78(19) . .
H15 C15 C16 119.78(18) . .
H25a C25 C4 109.5 . .
H25b C25 C4 109.5 . .
H25b C25 H25a 109.5 . .
H25c C25 C4 109.5 . .
H25c C25 H25a 109.5 . .
H25c C25 H25b 109.5 . .
H24a C24 C4 109.5 . .
H24b C24 C4 109.5 . .
H24b C24 H24a 109.5 . .
H24c C24 C4 109.5 . .
H24c C24 H24a 109.5 . .
H24c C24 H24b 109.5 . .
C16 C17 C18 116.7(3) . .
H17 C17 C18 121.64(18) . .
H17 C17 C16 121.64(19) . .
C17 C16 C15 122.0(3) . .
H16 C16 C15 119.02(18) . .
H16 C16 C17 119.02(19) . .

####################################################################### 
# 
# 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_RJ-5
_database_code_depnum_ccdc_archive 'CCDC 1031133'
_audit_update_record             
;
2014-10-27 deposited with the CCDC.
2016-02-10 downloaded from the CCDC.
;
_audit_creation_date             2014-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C21 H15 N5 O2'
_chemical_formula_sum            'C21 H15 N5 O2'
_chemical_formula_weight         369.39
_chemical_oxdiff_formula         C21H15N5O2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.0071(13)
_cell_length_b                   22.038(3)
_cell_length_c                   8.2460(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.552(12)
_cell_angle_gamma                90
_cell_volume                     1798.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2867
_cell_measurement_temperature    291.76(10)
_cell_measurement_theta_max      28.2840
_cell_measurement_theta_min      3.9310
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.3642
_exptl_crystal_description       block
_exptl_crystal_F_000             768.3317
_exptl_crystal_size_max          1.2
_exptl_crystal_size_mid          1.1
_exptl_crystal_size_min          0.46
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7788
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         28.78
_diffrn_reflns_theta_min         3.52
_diffrn_ambient_temperature      291.76(10)
_diffrn_detector_area_resol_mean 16.1279
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.8727
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -9.00   18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.5309  -99.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00   71.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8747   57.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega  -45.00   47.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8747  -57.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
  4 omega  -17.00   45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8747  -37.0000   30.0000 62
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0063379000
_diffrn_orient_matrix_UB_12      -0.0287745000
_diffrn_orient_matrix_UB_13      -0.0364668000
_diffrn_orient_matrix_UB_21      0.0205478000
_diffrn_orient_matrix_UB_22      0.0143723000
_diffrn_orient_matrix_UB_23      -0.0693180000
_diffrn_orient_matrix_UB_31      0.0682400000
_diffrn_orient_matrix_UB_32      -0.0016364000
_diffrn_orient_matrix_UB_33      0.0381535000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              29
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                3229
_reflns_number_total             4087
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.3173
_refine_diff_density_min         -0.3895
_refine_diff_density_rms         0.0969
_refine_ls_d_res_high            0.7381
_refine_ls_d_res_low             5.7927
_refine_ls_goodness_of_fit_ref   1.2132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4087
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.2132
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1719
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C2(H2), C3(H3), C4(H4),
 C5(H5), N1(H1)
2.b Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.04559(11) 0.58847(6) 0.59947(14) 0.0384(3) Uani 1.000000 .
O2 O -0.33482(11) 0.52094(7) 0.47814(14) 0.0470(4) Uani 1.000000 .
N5 N -0.15104(13) 0.72051(7) 0.50990(18) 0.0410(4) Uani 1.000000 .
N4 N -0.03814(13) 0.68534(7) 0.50618(17) 0.0357(3) Uani 1.000000 .
N1 N -0.44443(14) 0.54310(8) 0.69506(18) 0.0432(4) Uani 1.000000 .
C8 C -0.21920(15) 0.57617(7) 0.72147(18) 0.0298(3) Uani 1.000000 .
C14 C -0.23230(16) 0.68688(8) 0.5868(2) 0.0365(4) Uani 1.000000 .
C6 C -0.41332(16) 0.57035(8) 0.8514(2) 0.0367(4) Uani 1.000000 .
C16 C 0.07516(15) 0.71062(8) 0.4441(2) 0.0364(4) Uani 1.000000 .
C13 C -0.17444(14) 0.62994(7) 0.63358(18) 0.0306(4) Uani 1.000000 .
C7 C -0.33869(16) 0.54339(8) 0.6137(2) 0.0355(4) Uani 1.000000 .
C12 C -0.05301(14) 0.63168(7) 0.58049(18) 0.0310(4) Uani 1.000000 .
C11 C 0.01742(16) 0.53928(8) 0.69121(19) 0.0342(4) Uani 1.000000 .
N3 N 0.12244(17) 0.50116(9) 0.7131(2) 0.0501(4) Uani 1.000000 .
C1 C -0.28157(16) 0.59048(7) 0.87348(19) 0.0321(4) Uani 1.000000 .
C9 C -0.10083(16) 0.53231(7) 0.75035(19) 0.0323(4) Uani 1.000000 .
C10 C -0.11903(17) 0.47876(8) 0.8391(2) 0.0388(4) Uani 1.000000 .
C2 C -0.22764(19) 0.61868(8) 1.0181(2) 0.0409(4) Uani 1.000000 .
N2 N -0.1362(2) 0.43572(9) 0.9115(2) 0.0639(5) Uani 1.000000 .
C3 C -0.3085(2) 0.62511(9) 1.1403(2) 0.0508(5) Uani 1.000000 .
C21 C 0.0908(2) 0.77298(10) 0.4443(3) 0.0523(5) Uani 1.000000 .
C5 C -0.4963(2) 0.57691(10) 0.9700(3) 0.0504(5) Uani 1.000000 .
C4 C -0.4395(2) 0.60477(10) 1.1159(3) 0.0551(5) Uani 1.000000 .
C15 C -0.36626(18) 0.71062(10) 0.6142(3) 0.0559(6) Uani 1.000000 .
C17 C 0.1686(2) 0.67439(11) 0.3878(3) 0.0601(6) Uani 1.000000 .
C19 C 0.2940(2) 0.76239(12) 0.3323(3) 0.0624(6) Uani 1.000000 .
C20 C 0.2009(2) 0.79789(11) 0.3866(3) 0.0609(6) Uani 1.000000 .
C18 C 0.2780(2) 0.70050(13) 0.3314(4) 0.0751(7) Uani 1.000000 .
H17 H 0.1586(2) 0.63243(11) 0.3874(3) 0.0722(7) Uiso 1.000000 R
H18 H 0.3417(2) 0.67594(13) 0.2923(4) 0.0902(9) Uiso 1.000000 R
H19 H 0.3688(2) 0.77963(12) 0.2955(3) 0.0749(7) Uiso 1.000000 R
H20 H 0.2109(2) 0.83983(11) 0.3852(3) 0.0731(7) Uiso 1.000000 R
H21 H 0.0275(2) 0.79789(10) 0.4831(3) 0.0627(6) Uiso 1.000000 R
H2 H -0.13927(19) 0.63305(8) 1.0333(2) 0.0490(5) Uiso 1.000000 R
H3 H -0.2735(2) 0.64331(9) 1.2393(2) 0.0610(6) Uiso 1.000000 R
H4 H -0.4920(2) 0.60971(10) 1.1991(3) 0.0661(6) Uiso 1.000000 R
H5 H -0.5854(2) 0.56345(10) 0.9534(3) 0.0605(6) Uiso 1.000000 R
H1 H -0.52215(14) 0.52814(8) 0.65698(18) 0.0518(5) Uiso 1.000000 R
H15a H -0.3668(6) 0.7162(7) 0.7296(3) 0.0839(8) Uiso 1.000000 GR
H15b H -0.3830(7) 0.7488(4) 0.5589(16) 0.0839(8) Uiso 1.000000 GR
H15c H -0.4355(2) 0.6822(3) 0.5719(18) 0.0839(8) Uiso 1.000000 GR
H3a H 0.186(2) 0.5034(10) 0.645(3) 0.051(6) Uiso 1.000000 .
H3b H 0.114(3) 0.4655(13) 0.774(3) 0.072(7) Uiso 1.000000 .


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 C12 1.3634(19) . ?
O1 C11 1.375(2) . ?
O2 C7 1.2286(19) . ?
N5 N4 1.3743(19) . ?
N5 C14 1.329(2) . ?
N4 C16 1.425(2) . ?
N4 C12 1.350(2) . ?
N1 C6 1.414(2) . ?
N1 C7 1.334(2) . ?
N1 H1 0.8600 . ?
C8 C13 1.492(2) . ?
C8 C7 1.557(2) . ?
C8 C1 1.514(2) . ?
C8 C9 1.520(2) . ?
C14 C13 1.412(2) . ?
C14 C15 1.487(2) . ?
C6 C1 1.377(2) . ?
C6 C5 1.382(2) . ?
C16 C21 1.383(3) . ?
C16 C17 1.362(3) . ?
C13 C12 1.352(2) . ?
C11 N3 1.336(2) . ?
C11 C9 1.354(2) . ?
N3 H3a 0.91(2) . ?
N3 H3b 0.95(3) . ?
C1 C2 1.381(2) . ?
C9 C10 1.415(2) . ?
C10 N2 1.147(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C21 C20 1.377(3) . ?
C21 H21 0.9300 . ?
C5 C4 1.394(3) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C15 H15a 0.9600 . ?
C15 H15b 0.9600 . ?
C15 H15c 0.9600 . ?
C17 C18 1.378(3) . ?
C17 H17 0.9300 . ?
C19 C20 1.343(3) . ?
C19 C18 1.373(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C18 H18 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
C11 O1 C12 114.18(12) . . ?
C14 N5 N4 105.04(14) . . ?
C16 N4 N5 119.22(14) . . ?
C12 N4 N5 109.72(12) . . ?
C12 N4 C16 130.75(14) . . ?
C7 N1 C6 111.88(14) . . ?
H1 N1 C6 124.06(8) . . ?
H1 N1 C7 124.06(9) . . ?
C7 C8 C13 110.60(13) . . ?
C1 C8 C13 115.29(13) . . ?
C1 C8 C7 101.11(12) . . ?
C9 C8 C13 107.33(12) . . ?
C9 C8 C7 107.99(13) . . ?
C9 C8 C1 114.22(13) . . ?
C13 C14 N5 111.78(14) . . ?
C15 C14 N5 120.38(17) . . ?
C15 C14 C13 127.84(16) . . ?
C1 C6 N1 109.50(13) . . ?
C5 C6 N1 128.00(16) . . ?
C5 C6 C1 122.50(17) . . ?
C21 C16 N4 118.97(15) . . ?
C17 C16 N4 121.07(17) . . ?
C17 C16 C21 119.95(16) . . ?
C14 C13 C8 134.28(13) . . ?
C12 C13 C8 121.94(14) . . ?
C12 C13 C14 103.78(14) . . ?
N1 C7 O2 126.17(15) . . ?
C8 C7 O2 125.48(14) . . ?
C8 C7 N1 108.33(14) . . ?
N4 C12 O1 122.48(13) . . ?
C13 C12 O1 127.81(15) . . ?
C13 C12 N4 109.68(14) . . ?
N3 C11 O1 110.39(15) . . ?
C9 C11 O1 123.32(15) . . ?
C9 C11 N3 126.29(17) . . ?
H3a N3 C11 119.4(13) . . ?
H3b N3 C11 117.9(16) . . ?
H3b N3 H3a 120(2) . . ?
C6 C1 C8 109.14(13) . . ?
C2 C1 C8 130.70(15) . . ?
C2 C1 C6 120.16(15) . . ?
C11 C9 C8 125.03(15) . . ?
C10 C9 C8 117.02(14) . . ?
C10 C9 C11 117.88(15) . . ?
N2 C10 C9 178.7(2) . . ?
C3 C2 C1 118.48(17) . . ?
H2 C2 C1 120.76(10) . . ?
H2 C2 C3 120.76(12) . . ?
C4 C3 C2 120.45(18) . . ?
H3 C3 C2 119.77(12) . . ?
H3 C3 C4 119.77(11) . . ?
C20 C21 C16 119.47(19) . . ?
H21 C21 C16 120.27(10) . . ?
H21 C21 C20 120.27(14) . . ?
C4 C5 C6 116.48(18) . . ?
H5 C5 C6 121.76(12) . . ?
H5 C5 C4 121.76(12) . . ?
C5 C4 C3 121.92(17) . . ?
H4 C4 C3 119.04(11) . . ?
H4 C4 C5 119.04(12) . . ?
H15a C15 C14 109.5 . . ?
H15b C15 C14 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C14 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
C18 C17 C16 119.4(2) . . ?
H17 C17 C16 120.31(12) . . ?
H17 C17 C18 120.31(14) . . ?
C18 C19 C20 119.62(19) . . ?
H19 C19 C20 120.19(13) . . ?
H19 C19 C18 120.19(12) . . ?
C19 C20 C21 120.9(2) . . ?
H20 C20 C21 119.57(14) . . ?
H20 C20 C19 119.57(13) . . ?
C19 C18 C17 120.7(2) . . ?
H18 C18 C17 119.64(14) . . ?
H18 C18 C19 119.64(12) . . ?

####################################################################### 
# 
# 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_RJ-9
_database_code_depnum_ccdc_archive 'CCDC 1032132'
_audit_update_record             
;
2014-11-01 deposited with the CCDC.
2016-02-10 downloaded from the CCDC.
;
_audit_creation_date             2014-11-01
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_formula_moiety         'C23 H18 N2 O3'
_chemical_formula_sum            'C23 H18 N2 O3'
_chemical_formula_weight         370.41
_chemical_oxdiff_formula         C23H18N2O3
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_cell_length_a                   8.7800(4)
_cell_length_b                   11.9326(6)
_cell_length_c                   17.9072(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.842(5)
_cell_angle_gamma                90
_cell_volume                     1869.39(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1678
_cell_measurement_temperature    291.7(3)
_cell_measurement_theta_max      27.1050
_cell_measurement_theta_min      3.7880
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.3160
_exptl_crystal_description       block
_exptl_crystal_F_000             776.3828
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8306
_diffrn_reflns_theta_full        28.787972
_diffrn_reflns_theta_max         28.79
_diffrn_reflns_theta_min         3.18
_diffrn_ambient_temperature      291.7(3)
_diffrn_detector_area_resol_mean 16.1279
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.8766
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -76.00   1.0000   12.8400
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   16.00   1.0000   12.8400
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  -99.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -41.00  -14.00   1.0000   12.8400
omega____ theta____ kappa____ phi______ frames
    -      -20.2184   57.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   96.00   1.0000   12.8400
omega____ theta____ kappa____ phi______ frames
    -       22.5622   37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
  5 omega   76.00  102.00   1.0000   12.8400
omega____ theta____ kappa____ phi______ frames
    -       22.5622  178.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -30.00   31.00   1.0000   12.8400
omega____ theta____ kappa____ phi______ frames
    -       22.5622  -77.0000   60.0000 61
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0427960000
_diffrn_orient_matrix_UB_12      0.0003371000
_diffrn_orient_matrix_UB_13      -0.0318264000
_diffrn_orient_matrix_UB_21      -0.0057680000
_diffrn_orient_matrix_UB_22      0.0592928000
_diffrn_orient_matrix_UB_23      -0.0017138000
_diffrn_orient_matrix_UB_31      0.0685542000
_diffrn_orient_matrix_UB_32      0.0046806000
_diffrn_orient_matrix_UB_33      0.0237699000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -11
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              -8
_reflns_number_gt                2729
_reflns_number_total             4262
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.379893
_refine_diff_density_min         -0.376262
_refine_diff_density_rms         0.073448
_refine_ls_d_res_high            0.737931
_refine_ls_d_res_low             6.413591
_refine_ls_goodness_of_fit_ref   1.027567
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.090253
_refine_ls_R_factor_gt           0.052441
_refine_ls_restrained_S_all      1.027567
_refine_ls_shift/su_max          0.0018
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.135589
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O -0.00543(13) -0.02169(11) 0.39646(7) 0.0395(3) Uani 1.000000 .
O22 O 0.01181(14) 0.27618(12) 0.52802(7) 0.0450(4) Uani 1.000000 .
O23 O -0.14448(15) 0.35582(12) 0.35833(8) 0.0478(4) Uani 1.000000 .
N26 N 0.20900(19) -0.09187(14) 0.45028(9) 0.0448(4) Uani 1.000000 .
N25 N 0.4620(2) 0.13977(17) 0.49400(13) 0.0749(7) Uani 1.000000 .
C11 C 0.23253(18) 0.38140(16) 0.38985(10) 0.0320(4) Uani 1.000000 .
C10 C 0.13703(19) 0.00344(16) 0.42887(10) 0.0332(4) Uani 1.000000 .
C2 C -0.09852(19) 0.06453(16) 0.36973(10) 0.0328(4) Uani 1.000000 .
C14 C 0.18212(18) 0.28268(16) 0.35339(10) 0.0315(4) Uani 1.000000 .
C7 C -0.05926(18) 0.17196(16) 0.37538(10) 0.0304(4) Uani 1.000000 .
C8 C 0.09656(18) 0.21170(15) 0.40693(10) 0.0304(4) Uani 1.000000 .
C18 C 0.32256(19) 0.46248(17) 0.35777(12) 0.0401(5) Uani 1.000000 .
C6 C -0.1743(2) 0.25636(17) 0.35133(10) 0.0357(5) Uani 1.000000 .
C13 C 0.08553(19) 0.29530(16) 0.47490(10) 0.0333(4) Uani 1.000000 .
C9 C 0.18956(19) 0.10990(16) 0.43417(10) 0.0328(4) Uani 1.000000 .
C12 C 0.1803(2) 0.39353(16) 0.46161(10) 0.0350(4) Uani 1.000000 .
C4 C -0.3284(2) 0.10498(18) 0.28051(12) 0.0450(5) Uani 1.000000 .
C21 C 0.2180(2) 0.26424(18) 0.28196(10) 0.0390(5) Uani 1.000000 .
C3 C -0.2461(2) 0.02034(18) 0.33362(12) 0.0438(5) Uani 1.000000 .
C24 C 0.3403(2) 0.12665(17) 0.46758(12) 0.0445(5) Uani 1.000000 .
C16 C 0.3115(2) 0.56763(19) 0.47283(14) 0.0527(6) Uani 1.000000 .
C17 C 0.3620(2) 0.55705(18) 0.40240(13) 0.0496(6) Uani 1.000000 .
C5 C -0.3308(2) 0.21673(18) 0.32185(13) 0.0496(6) Uani 1.000000 .
C15 C 0.2182(2) 0.48750(18) 0.50337(12) 0.0444(5) Uani 1.000000 .
C20 C 0.3075(2) 0.34576(19) 0.24772(12) 0.0465(5) Uani 1.000000 .
C19 C 0.3596(2) 0.44012(19) 0.28396(12) 0.0457(5) Uani 1.000000 .
C27 C -0.2451(3) 0.1185(2) 0.20967(12) 0.0612(7) Uani 1.000000 .
C28 C -0.4914(2) 0.0628(2) 0.25911(16) 0.0730(9) Uani 1.000000 .
H21 H 0.1849(2) 0.19989(18) 0.25619(10) 0.0468(6) Uiso 1.000000 R
H20 H 0.3313(2) 0.33410(19) 0.19869(12) 0.0557(6) Uiso 1.000000 R
H19 H 0.4201(2) 0.49039(19) 0.25997(12) 0.0548(6) Uiso 1.000000 R
H15 H 0.1829(2) 0.49761(18) 0.55044(12) 0.0533(6) Uiso 1.000000 R
H16 H 0.3406(2) 0.63051(19) 0.50123(14) 0.0632(7) Uiso 1.000000 R
H17 H 0.4227(2) 0.61289(18) 0.38412(13) 0.0596(7) Uiso 1.000000 R
H3a H -0.2261(2) -0.04716(18) 0.30588(12) 0.0526(6) Uiso 1.000000 R
H3b H -0.3122(2) 0.00035(18) 0.37228(12) 0.0526(6) Uiso 1.000000 R
H5a H -0.3941(2) 0.20926(18) 0.36345(13) 0.0595(7) Uiso 1.000000 R
H5b H -0.3772(2) 0.27298(18) 0.28807(13) 0.0595(7) Uiso 1.000000 R
H27a H -0.1447(7) 0.1480(12) 0.22261(16) 0.0918(10) Uiso 1.000000 G
H27b H -0.2371(15) 0.0469(3) 0.1859(5) 0.0918(10) Uiso 1.000000 G
H27c H -0.3012(10) 0.1691(10) 0.1759(4) 0.0918(10) Uiso 1.000000 G
H28a H -0.4872(2) -0.0111(7) 0.2381(10) 0.1096(13) Uiso 1.000000 G
H28b H -0.5471(7) 0.0605(14) 0.3030(2) 0.1096(13) Uiso 1.000000 G
H28c H -0.5418(7) 0.1125(9) 0.2228(8) 0.1096(13) Uiso 1.000000 G
H26a H 0.2780(11) -0.0765(2) 0.4858(6) 0.0538(5) Uiso 1.000000 G
H26b H 0.1447(3) -0.1387(5) 0.4662(8) 0.0538(5) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C10 1.367(2) .
O1 C2 1.375(2) .
O22 C13 1.216(2) .
O23 C6 1.220(2) .
N26 C10 1.341(2) .
N26 H26a 0.8600 .
N26 H26b 0.8600 .
N25 C24 1.142(2) .
C11 C14 1.400(3) .
C11 C18 1.403(3) .
C11 C12 1.408(3) .
C10 C9 1.352(3) .
C2 C7 1.329(2) .
C2 C3 1.495(2) .
C14 C8 1.524(2) .
C14 C21 1.361(2) .
C7 C8 1.512(2) .
C7 C6 1.465(2) .
C8 C13 1.583(3) .
C8 C9 1.521(2) .
C18 C17 1.409(3) .
C18 C19 1.413(3) .
C6 C5 1.506(2) .
C13 C12 1.468(3) .
C9 C24 1.420(2) .
C12 C15 1.373(3) .
C4 C3 1.527(3) .
C4 C5 1.526(3) .
C4 C27 1.525(3) .
C4 C28 1.535(3) .
C21 C20 1.421(3) .
C21 H21 0.9300 .
C3 H3a 0.9700 .
C3 H3b 0.9700 .
C16 C17 1.377(3) .
C16 C15 1.400(3) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C5 H5a 0.9700 .
C5 H5b 0.9700 .
C15 H15 0.9300 .
C20 C19 1.359(3) .
C20 H20 0.9300 .
C19 H19 0.9300 .
C27 H27a 0.9600 .
C27 H27b 0.9600 .
C27 H27c 0.9600 .
C28 H28a 0.9600 .
C28 H28b 0.9600 .
C28 H28c 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
C2 O1 C10 118.66(14) . .
H26a N26 C10 108.44(11) . .
H26b N26 C10 109.80(10) . .
H26b N26 H26a 109.5 . .
C18 C11 C14 123.79(18) . .
C12 C11 C14 113.42(17) . .
C12 C11 C18 122.76(18) . .
N26 C10 O1 109.12(16) . .
C9 C10 O1 122.03(16) . .
C9 C10 N26 128.82(16) . .
C7 C2 O1 123.54(15) . .
C3 C2 O1 110.79(16) . .
C3 C2 C7 125.67(17) . .
C8 C14 C11 109.11(15) . .
C21 C14 C11 119.01(18) . .
C21 C14 C8 131.84(18) . .
C8 C7 C2 123.49(16) . .
C6 C7 C2 118.20(16) . .
C6 C7 C8 118.29(16) . .
C7 C8 C14 114.70(14) . .
C13 C8 C14 101.47(14) . .
C13 C8 C7 111.89(14) . .
C9 C8 C14 111.46(14) . .
C9 C8 C7 108.29(15) . .
C9 C8 C13 108.84(14) . .
C17 C18 C11 116.11(19) . .
C19 C18 C11 115.78(19) . .
C19 C18 C17 128.1(2) . .
C7 C6 O23 120.12(16) . .
C5 C6 O23 121.56(17) . .
C5 C6 C7 118.25(17) . .
C8 C13 O22 123.66(17) . .
C12 C13 O22 128.50(18) . .
C12 C13 C8 107.83(15) . .
C8 C9 C10 123.86(14) . .
C24 C9 C10 117.52(17) . .
C24 C9 C8 118.61(16) . .
C13 C12 C11 107.37(16) . .
C15 C12 C11 119.91(18) . .
C15 C12 C13 132.69(18) . .
C5 C4 C3 107.52(16) . .
C27 C4 C3 110.66(17) . .
C27 C4 C5 109.8(2) . .
C28 C4 C3 108.71(18) . .
C28 C4 C5 110.94(17) . .
C28 C4 C27 109.22(18) . .
C20 C21 C14 118.37(19) . .
H21 C21 C14 120.82(12) . .
H21 C21 C20 120.82(12) . .
C4 C3 C2 112.56(16) . .
H3a C3 C2 109.08(11) . .
H3a C3 C4 109.08(11) . .
H3b C3 C2 109.08(11) . .
H3b C3 C4 109.08(11) . .
H3b C3 H3a 107.8 . .
C9 C24 N25 179.5(2) . .
C15 C16 C17 122.6(2) . .
H16 C16 C17 118.69(13) . .
H16 C16 C15 118.69(13) . .
C16 C17 C18 120.7(2) . .
H17 C17 C18 119.67(12) . .
H17 C17 C16 119.67(13) . .
C4 C5 C6 113.26(16) . .
H5a C5 C6 108.92(11) . .
H5a C5 C4 108.92(12) . .
H5b C5 C6 108.92(12) . .
H5b C5 C4 108.92(12) . .
H5b C5 H5a 107.7 . .
C16 C15 C12 117.9(2) . .
H15 C15 C12 121.06(12) . .
H15 C15 C16 121.06(13) . .
C19 C20 C21 122.5(2) . .
H20 C20 C21 118.77(12) . .
H20 C20 C19 118.77(12) . .
C20 C19 C18 120.6(2) . .
H19 C19 C18 119.72(12) . .
H19 C19 C20 119.72(12) . .
H27a C27 C4 109.5 . .
H27b C27 C4 109.5 . .
H27b C27 H27a 109.5 . .
H27c C27 C4 109.5 . .
H27c C27 H27a 109.5 . .
H27c C27 H27b 109.5 . .
H28a C28 C4 109.5 . .
H28b C28 C4 109.5 . .
H28b C28 H28a 109.5 . .
H28c C28 C4 109.5 . .
H28c C28 H28a 109.5 . .
H28c C28 H28b 109.5 . .

