# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_2015sot0019
_database_code_depnum_ccdc_archive 'CCDC 1060587'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2016-09-06 downloaded from the CCDC.
;
_audit_creation_date             2015-04-20
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 N2 O3'
_chemical_formula_sum            'C20 H16 N2 O3'
_chemical_formula_weight         332.35
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.4411(5)
_cell_length_b                   16.0503(12)
_cell_length_c                   30.612(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3164.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4309
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.3390
_cell_measurement_theta_min      2.5320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lath
_exptl_crystal_F_000             1392
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1638
_diffrn_reflns_av_unetI/netI     0.0777
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            25527
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.013
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_min         3.230
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -83.00   53.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   18.0000  120.0000 136

#__ type_ start__ end____ width___ exp.time_
  2 omega  -84.00    4.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -54.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
  3 omega  -95.00   36.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -18.0000  -30.0000 131

#__ type_ start__ end____ width___ exp.time_
  4 omega  -54.00   25.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   72.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
  5 omega -112.00  -59.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -54.0000   90.0000 53
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0179192000
_diffrn_orient_matrix_UB_12      -0.0061400000
_diffrn_orient_matrix_UB_13      0.0226338000
_diffrn_orient_matrix_UB_21      0.0367560000
_diffrn_orient_matrix_UB_22      -0.0408263000
_diffrn_orient_matrix_UB_23      -0.0043075000
_diffrn_orient_matrix_UB_31      0.1022970000
_diffrn_orient_matrix_UB_32      0.0157314000
_diffrn_orient_matrix_UB_33      -0.0024219000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1639
_reflns_number_total             2789
_reflns_odcompleteness_completeness 95.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.03
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1353
_refine_ls_R_factor_gt           0.0810
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+2.6528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1865
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C18(H18)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3721(4) 0.78738(16) 0.62192(9) 0.0387(7) Uani 1 1 d . . . . .
O2 O 0.3696(4) 0.51335(16) 0.71968(9) 0.0367(7) Uani 1 1 d . . . . .
O3 O 0.3494(4) 0.49198(15) 0.63569(9) 0.0367(7) Uani 1 1 d . . . . .
N1 N 0.3650(4) 0.75015(19) 0.78175(11) 0.0310(8) Uani 1 1 d . . . . .
N2 N 0.3659(5) 0.6640(2) 0.83849(11) 0.0349(8) Uani 1 1 d . . . . .
C1 C 0.2156(7) 0.6670(2) 0.54846(14) 0.0399(11) Uani 1 1 d . . . . .
H1 H 0.0922 0.6849 0.5612 0.048 Uiso 1 1 calc R . . . .
C2 C 0.2341(8) 0.6655(3) 0.50320(15) 0.0472(12) Uani 1 1 d . . . . .
H2 H 0.1236 0.6824 0.4858 0.057 Uiso 1 1 calc R . . . .
C3 C 0.4160(7) 0.6390(3) 0.48433(16) 0.0508(13) Uani 1 1 d . . . . .
H3 H 0.4273 0.6361 0.4541 0.061 Uiso 1 1 calc R . . . .
C4 C 0.5821(7) 0.6165(3) 0.51040(15) 0.0486(12) Uani 1 1 d . . . . .
H4 H 0.7064 0.5999 0.4976 0.058 Uiso 1 1 calc R . . . .
C5 C 0.5644(6) 0.6185(3) 0.55505(14) 0.0421(11) Uani 1 1 d . . . . .
H5 H 0.6775 0.6037 0.5723 0.050 Uiso 1 1 calc R . . . .
C6 C 0.3798(6) 0.6421(2) 0.57487(13) 0.0329(10) Uani 1 1 d . . . . .
C7 C 0.3624(6) 0.6413(2) 0.62325(12) 0.0283(9) Uani 1 1 d . . . . .
C8 C 0.3651(6) 0.7241(2) 0.64435(13) 0.0327(10) Uani 1 1 d . . . . .
C9 C 0.3618(5) 0.7308(2) 0.69249(13) 0.0289(9) Uani 1 1 d . . . . .
C10 C 0.3655(5) 0.6611(2) 0.71815(13) 0.0295(9) Uani 1 1 d . . . . .
C11 C 0.3643(5) 0.5768(2) 0.69774(13) 0.0311(9) Uani 1 1 d . . . . .
C12 C 0.3565(6) 0.5723(2) 0.64850(12) 0.0300(9) Uani 1 1 d . . . . .
C13 C 0.2444(7) 0.4686(3) 0.59545(13) 0.0401(11) Uani 1 1 d . . . . .
H13A H 0.2625 0.4094 0.5904 0.048 Uiso 1 1 calc R . . . .
H13B H 0.3065 0.4982 0.5711 0.048 Uiso 1 1 calc R . . . .
C14 C 0.0183(7) 0.4883(3) 0.59747(16) 0.0522(13) Uani 1 1 d . . . . .
H14A H -0.0460 0.4735 0.5703 0.078 Uiso 1 1 calc GR . . . .
H14B H 0.0001 0.5468 0.6027 0.078 Uiso 1 1 calc GR . . . .
H14C H -0.0446 0.4572 0.6208 0.078 Uiso 1 1 calc GR . . . .
C15 C 0.3588(5) 0.8119(2) 0.71197(13) 0.0301(9) Uani 1 1 d . . . . .
H15 H 0.3551 0.8590 0.6943 0.036 Uiso 1 1 calc R . . . .
C16 C 0.3612(6) 0.8200(2) 0.75544(14) 0.0336(10) Uani 1 1 d . . . . .
H16 H 0.3604 0.8728 0.7680 0.040 Uiso 1 1 calc R . . . .
C17 C 0.3652(5) 0.6688(2) 0.76444(13) 0.0291(9) Uani 1 1 d . . . . .
C18 C 0.3658(5) 0.6181(2) 0.80078(13) 0.0325(9) Uani 1 1 d . . . . .
H18 H 0.3660 0.5602 0.7998 0.039 Uiso 1 1 calc R . . . .
C19 C 0.3646(6) 0.7437(3) 0.82651(13) 0.0339(10) Uani 1 1 d . . . . .
C20 C 0.3635(6) 0.8166(2) 0.85583(13) 0.0413(11) Uani 1 1 d . . . . .
H20A H 0.4753 0.8533 0.8481 0.062 Uiso 1 1 calc GR . . . .
H20B H 0.3806 0.7985 0.8855 0.062 Uiso 1 1 calc GR . . . .
H20C H 0.2338 0.8456 0.8530 0.062 Uiso 1 1 calc GR . . . .


_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 C8 1.227(4) . ?
O2 C11 1.221(4) . ?
O3 C12 1.348(4) . ?
O3 C13 1.455(4) . ?
N1 C16 1.380(5) . ?
N1 C17 1.409(4) . ?
N1 C19 1.374(5) . ?
N2 C18 1.369(5) . ?
N2 C19 1.331(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.391(6) . ?
C1 C6 1.390(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(5) . ?
C6 C7 1.485(5) . ?
C7 C8 1.478(5) . ?
C7 C12 1.350(5) . ?
C8 C9 1.478(5) . ?
C9 C10 1.367(5) . ?
C9 C15 1.431(5) . ?
C10 C11 1.490(5) . ?
C10 C17 1.422(5) . ?
C11 C12 1.510(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.491(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C16 1.337(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.476(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 O3 C13 120.6(3) . . ?
C16 N1 C17 122.2(3) . . ?
C19 N1 C16 130.0(3) . . ?
C19 N1 C17 107.8(3) . . ?
C19 N2 C18 106.5(3) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C6 C1 C2 120.6(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(4) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 121.7(4) . . ?
C5 C6 C1 118.4(4) . . ?
C5 C6 C7 119.9(4) . . ?
C8 C7 C6 115.2(3) . . ?
C12 C7 C6 125.5(3) . . ?
C12 C7 C8 119.2(4) . . ?
O1 C8 C7 120.0(4) . . ?
O1 C8 C9 119.8(3) . . ?
C7 C8 C9 120.1(3) . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 C15 120.3(4) . . ?
C15 C9 C8 118.8(3) . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 C17 120.1(3) . . ?
C17 C10 C11 119.8(3) . . ?
O2 C11 C10 121.8(4) . . ?
O2 C11 C12 120.7(4) . . ?
C10 C11 C12 117.6(3) . . ?
O3 C12 C7 128.2(4) . . ?
O3 C12 C11 109.7(3) . . ?
C7 C12 C11 122.1(4) . . ?
O3 C13 H13A 109.4 . . ?
O3 C13 H13B 109.4 . . ?
O3 C13 C14 111.4(3) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15 119.9 . . ?
C16 C15 C9 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
N1 C16 H16 119.9 . . ?
C15 C16 N1 120.1(3) . . ?
C15 C16 H16 119.9 . . ?
N1 C17 C10 117.1(3) . . ?
C18 C17 N1 104.1(3) . . ?
C18 C17 C10 138.8(4) . . ?
N2 C18 C17 111.3(4) . . ?
N2 C18 H18 124.3 . . ?
C17 C18 H18 124.3 . . ?
N1 C19 C20 123.1(4) . . ?
N2 C19 N1 110.3(3) . . ?
N2 C19 C20 126.5(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_submission    2015-03-19
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id FCR/7506/17
_olex2_submission_special_instructions 'No special instructions were received'
