# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_sjf_161228_2
_database_code_depnum_ccdc_archive 'CCDC 1525815'
_audit_update_record             
;
2017-01-06 deposited with the CCDC.
2017-05-16 downloaded from the CCDC.
;
_audit_creation_date             2016-12-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_formula_moiety         'C19 H15 N3 O4'
_chemical_formula_sum            'C19 H15 N3 O4'
_chemical_formula_weight         349.35
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 0.01920 0.00962 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 0.05239 0.03377 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 0.03256 0.01839 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.7171(4)
_cell_length_b                   10.6392(6)
_cell_length_c                   11.0090(4)
_cell_angle_alpha                110.700(5)
_cell_angle_beta                 100.085(4)
_cell_angle_gamma                101.913(5)
_cell_volume                     796.35(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4732
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.0620
_cell_measurement_theta_min      4.9340
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4568
_exptl_crystal_description       block
_exptl_crystal_F_000             365.2760
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6140
_diffrn_reflns_theta_full        67.0733
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.97
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9891
_diffrn_measured_fraction_theta_max 0.9544
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  20.00   1.00    2.00    --  -44.52  57.00  60.00   83
  2  ω     75.00 117.00   1.00    2.00    --   44.52 125.00-150.00   42
  3  ω    138.00 171.00   1.00    4.00    --  100.00  30.00-120.00   33
  4  ω    102.00 128.00   1.00    4.00    --  100.00  30.00-120.00   26
  5  ω     39.00 120.00   1.00    4.00    --  100.00 -45.00 -90.00   81
  6  ω     74.00  99.00   1.00    4.00    --  100.00-125.00 -90.00   25
  7  ω     40.00 101.00   1.00    4.00    --  100.00 -94.00   0.00   61
  8  ω     28.00 116.00   1.00    4.00    --  100.00-125.00 -30.00   88
  9  ω     36.00 118.00   1.00    4.00    --  100.00-125.00-150.00   82
 10  ω     27.00 100.00   1.00    4.00    --  100.00 -77.00  60.00   73
 11  ω     33.00 118.00   1.00    4.00    --  100.00 -45.00 150.00   85
 12  ω     92.00 162.00   1.00    4.00    --  100.00  45.00 120.00   70
 13  ω     21.00  89.00   1.00    2.00    --   44.52  57.00-180.00   68
 14  ω    -52.00 -26.00   1.00    4.00    --  -90.00  45.00-150.00   26
 15  ω   -105.00 -79.00   1.00    4.00    --  -90.00  45.00-150.00   26
 16  ω   -114.00 -20.00   1.00    2.00    --  -44.52 -57.00 -90.00   94
 17  ω   -168.00 -51.00   1.00    4.00    --  -90.00 -15.00   0.00  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1907092000
_diffrn_orient_matrix_UB_12      -0.0038465000
_diffrn_orient_matrix_UB_13      0.0665959000
_diffrn_orient_matrix_UB_21      -0.0718679000
_diffrn_orient_matrix_UB_22      -0.1611032000
_diffrn_orient_matrix_UB_23      -0.0529003000
_diffrn_orient_matrix_UB_31      0.0582332000
_diffrn_orient_matrix_UB_32      -0.0146414000
_diffrn_orient_matrix_UB_33      -0.1300733000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2585
_reflns_number_total             2817
_reflns_odcompleteness_completeness 98.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.4231
_refine_diff_density_min         -0.4943
_refine_diff_density_rms         0.0459
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             8.8953
_refine_ls_goodness_of_fit_ref   1.0489
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2817
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.0489
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²+0.2672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1054
_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:
 C16(H16), C14(H14), C19(H19), C17(H17), C23(H23), C10(H10), C13(H13), N4(H4),
 C11(H11)
2.b Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c), C26(H26a,H26b,H26c)
;
_atom_sites_solution_primary     direct
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 0.05367(12) 0.45217(10) 0.27343(9) 0.0190(2) Uani 1.000000 .
O2 O 0.55341(13) 0.43376(11) 0.77429(10) 0.0241(2) Uani 1.000000 .
O3 O 0.54650(14) 0.65744(11) 0.87027(10) 0.0276(3) Uani 1.000000 .
N4 N 0.16586(16) 0.92058(12) 0.58573(12) 0.0206(3) Uani 1.000000 .
N5 N -0.03707(15) 0.82859(12) 0.37513(12) 0.0203(3) Uani 1.000000 .
C6 C 0.37826(18) 0.51616(14) 0.63947(13) 0.0181(3) Uani 1.000000 .
N7 N -0.09074(16) 0.59731(12) 0.20643(12) 0.0204(3) Uani 1.000000 .
O8 O 0.89776(14) 1.07775(11) 0.88268(11) 0.0305(3) Uani 1.000000 .
C9 C 0.20957(17) 0.59912(14) 0.49461(13) 0.0167(3) Uani 1.000000 .
C10 C 0.66765(19) 0.96389(14) 0.67885(14) 0.0207(3) Uani 1.000000 .
C11 C -0.11591(19) 0.72430(15) 0.25372(14) 0.0212(3) Uani 1.000000 .
C12 C 0.11641(17) 0.67579(14) 0.43172(13) 0.0172(3) Uani 1.000000 .
C13 C 0.48762(19) 0.92122(14) 0.60257(14) 0.0195(3) Uani 1.000000 .
C14 C 0.33245(18) 0.38388(14) 0.53329(14) 0.0191(3) Uani 1.000000 .
C15 C 0.08611(18) 0.80889(14) 0.46594(14) 0.0183(3) Uani 1.000000 .
C16 C 0.22377(18) 0.35531(14) 0.40704(14) 0.0194(3) Uani 1.000000 .
C17 C 0.3970(2) 1.03101(15) 0.80267(14) 0.0229(3) Uani 1.000000 .
C18 C 0.02289(18) 0.58021(14) 0.30074(14) 0.0178(3) Uani 1.000000 .
C19 C 0.31672(18) 0.62497(14) 0.62167(13) 0.0179(3) Uani 1.000000 .
C20 C 0.16573(17) 0.46442(14) 0.39188(13) 0.0173(3) Uani 1.000000 .
C21 C 0.34976(19) 0.95444(14) 0.66415(14) 0.0191(3) Uani 1.000000 .
C22 C 0.7147(2) 1.04079(14) 0.81777(15) 0.0231(3) Uani 1.000000 .
C23 C 0.5788(2) 1.07523(15) 0.88023(15) 0.0256(3) Uani 1.000000 .
C24 C 0.49953(19) 0.54618(15) 0.77379(14) 0.0199(3) Uani 1.000000 .
C25 C 0.6757(2) 0.45170(18) 0.89919(15) 0.0284(4) Uani 1.000000 .
C26 C 0.9556(2) 1.17283(19) 1.02126(16) 0.0373(4) Uani 1.000000 .
H16 H 0.19095(18) 0.26546(14) 0.33480(14) 0.0232(4) Uiso 1.000000 R
H14 H 0.37688(18) 0.31222(14) 0.54819(14) 0.0229(4) Uiso 1.000000 R
H19 H 0.34719(18) 0.71425(14) 0.69436(13) 0.0214(4) Uiso 1.000000 R
H17 H 0.3040(2) 1.05362(15) 0.84529(14) 0.0275(4) Uiso 1.000000 R
H23 H 0.6098(2) 1.12840(15) 0.97484(15) 0.0308(4) Uiso 1.000000 R
H10 H 0.76038(19) 0.94058(14) 0.63621(14) 0.0249(4) Uiso 1.000000 R
H13 H 0.45720(19) 0.86906(14) 0.50781(14) 0.0234(4) Uiso 1.000000 R
H4 H 0.09942(16) 0.97607(12) 0.61729(12) 0.0247(3) Uiso 1.000000 R
H11 H -0.20073(19) 0.74267(15) 0.19322(14) 0.0254(4) Uiso 1.000000 R
H25a H 0.7245(13) 0.3710(6) 0.8835(3) 0.0426(5) Uiso 1.000000 GR
H25b H 0.7776(9) 0.5378(7) 0.9311(6) 0.0426(5) Uiso 1.000000 GR
H25c H 0.6076(4) 0.4584(12) 0.9674(4) 0.0426(5) Uiso 1.000000 GR
H26a H 0.9162(16) 1.2569(6) 1.0310(2) 0.0559(6) Uiso 1.000000 GR
H26b H 0.9002(15) 1.1273(5) 1.0744(3) 0.0559(6) Uiso 1.000000 GR
H26c H 1.0899(3) 1.1995(11) 1.0537(4) 0.0559(6) Uiso 1.000000 GR


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 C18 1.3681(16) . ?
O1 C20 1.3797(16) . ?
O2 C24 1.3463(17) . ?
O2 C25 1.4503(17) . ?
O3 C24 1.2083(18) . ?
N4 C15 1.3550(18) . ?
N4 C21 1.4244(17) . ?
N4 H4 0.8800 . ?
N5 C11 1.3326(18) . ?
N5 C15 1.3581(17) . ?
C6 C14 1.400(2) . ?
C6 C19 1.3996(19) . ?
C6 C24 1.4908(19) . ?
N7 C11 1.3344(18) . ?
N7 C18 1.3269(18) . ?
O8 C22 1.3711(17) . ?
O8 C26 1.4263(19) . ?
C9 C12 1.4589(18) . ?
C9 C19 1.3947(18) . ?
C9 C20 1.4026(19) . ?
C10 C13 1.3795(19) . ?
C10 C22 1.392(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C15 1.4116(19) . ?
C12 C18 1.3893(19) . ?
C13 C21 1.398(2) . ?
C13 H13 0.9500 . ?
C14 C16 1.3840(19) . ?
C14 H14 0.9500 . ?
C16 C20 1.3790(19) . ?
C16 H16 0.9500 . ?
C17 C21 1.388(2) . ?
C17 C23 1.394(2) . ?
C17 H17 0.9500 . ?
C19 H19 0.9500 . ?
C22 C23 1.392(2) . ?
C23 H23 0.9500 . ?
C25 H25a 0.9800 . ?
C25 H25b 0.9800 . ?
C25 H25c 0.9800 . ?
C26 H26a 0.9800 . ?
C26 H26b 0.9800 . ?
C26 H26c 0.9800 . ?

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
C20 O1 C18 105.54(10) . . ?
C25 O2 C24 116.40(12) . . ?
C21 N4 C15 124.56(11) . . ?
H4 N4 C15 117.72(7) . . ?
H4 N4 C21 117.72(7) . . ?
C15 N5 C11 118.68(12) . . ?
C19 C6 C14 121.18(13) . . ?
C24 C6 C14 120.63(12) . . ?
C24 C6 C19 118.16(12) . . ?
C18 N7 C11 110.99(12) . . ?
C26 O8 C22 116.94(12) . . ?
C19 C9 C12 137.36(12) . . ?
C20 C9 C12 104.33(11) . . ?
C20 C9 C19 118.28(12) . . ?
C22 C10 C13 120.59(13) . . ?
H10 C10 C13 119.70(8) . . ?
H10 C10 C22 119.70(8) . . ?
N7 C11 N5 128.18(13) . . ?
H11 C11 N5 115.91(8) . . ?
H11 C11 N7 115.91(8) . . ?
C15 C12 C9 139.63(13) . . ?
C18 C12 C9 105.93(12) . . ?
C18 C12 C15 114.29(12) . . ?
C21 C13 C10 120.27(13) . . ?
H13 C13 C10 119.87(8) . . ?
H13 C13 C21 119.87(8) . . ?
C16 C14 C6 121.38(12) . . ?
H14 C14 C6 119.31(8) . . ?
H14 C14 C16 119.31(8) . . ?
N5 C15 N4 115.71(12) . . ?
C12 C15 N4 125.41(12) . . ?
C12 C15 N5 118.84(12) . . ?
C20 C16 C14 116.33(13) . . ?
H16 C16 C14 121.84(8) . . ?
H16 C16 C20 121.84(8) . . ?
C23 C17 C21 121.02(13) . . ?
H17 C17 C21 119.49(8) . . ?
H17 C17 C23 119.49(8) . . ?
N7 C18 O1 119.11(12) . . ?
C12 C18 O1 112.06(11) . . ?
C12 C18 N7 128.80(13) . . ?
C9 C19 C6 118.38(12) . . ?
H19 C19 C6 120.81(8) . . ?
H19 C19 C9 120.81(8) . . ?
C9 C20 O1 112.10(11) . . ?
C16 C20 O1 123.45(12) . . ?
C16 C20 C9 124.44(12) . . ?
C13 C21 N4 120.93(12) . . ?
C17 C21 N4 119.88(12) . . ?
C17 C21 C13 119.00(13) . . ?
C10 C22 O8 115.31(13) . . ?
C23 C22 O8 124.98(13) . . ?
C23 C22 C10 119.71(13) . . ?
C22 C23 C17 119.40(13) . . ?
H23 C23 C17 120.30(8) . . ?
H23 C23 C22 120.30(8) . . ?
O3 C24 O2 123.69(13) . . ?
C6 C24 O2 111.47(12) . . ?
C6 C24 O3 124.83(13) . . ?
H25a C25 O2 109.5 . . ?
H25b C25 O2 109.5 . . ?
H25b C25 H25a 109.5 . . ?
H25c C25 O2 109.5 . . ?
H25c C25 H25a 109.5 . . ?
H25c C25 H25b 109.5 . . ?
H26a C26 O8 109.5 . . ?
H26b C26 O8 109.5 . . ?
H26b C26 H26a 109.5 . . ?
H26c C26 O8 109.5 . . ?
H26c C26 H26a 109.5 . . ?
H26c C26 H26b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.143
_oxdiff_exptl_absorpt_empirical_full_min 0.526
