# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_160323_lg4_138_3
_audit_block_doi                 10.5517/ccdc.csd.cc1m7vwl
_database_code_depnum_ccdc_archive 'CCDC 1497110'
_audit_update_record             
;
2016-08-01 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2016-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H18 N2 O3'
_chemical_formula_sum            'C20 H18 N2 O3'
_chemical_formula_weight         334.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 h10 O2 n2'
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'

_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'

_cell_length_a                   13.2268(10)
_cell_length_b                   8.5916(5)
_cell_length_c                   15.6448(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.955(9)
_cell_angle_gamma                90.00
_cell_volume                     1681.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1682
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.4965
_cell_measurement_theta_min      3.2504
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.32
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6492
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.26
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0272817000
_diffrn_orient_matrix_UB_12      0.0384840000
_diffrn_orient_matrix_UB_13      0.0411639000
_diffrn_orient_matrix_UB_21      0.0491158000
_diffrn_orient_matrix_UB_22      -0.0102240000
_diffrn_orient_matrix_UB_23      -0.0084272000
_diffrn_orient_matrix_UB_31      -0.0075713000
_diffrn_orient_matrix_UB_32      0.0723116000
_diffrn_orient_matrix_UB_33      -0.0231127000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2326
_reflns_number_total             3061
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0521P)²+0.3734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1148
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.83763(10) 0.60970(15) 0.20619(8) 0.0378(3) Uani 1 d . . .
O2 O 0.62570(10) 0.42339(14) 0.18345(9) 0.0386(3) Uani 1 d . . .
O3 O 0.46339(10) 0.50511(13) 0.09775(9) 0.0349(3) Uani 1 d . . .
N1 N 0.76191(11) 0.43497(17) 0.47465(10) 0.0317(4) Uani 1 d . . .
N2 N 0.79824(11) 0.57389(16) 0.33605(9) 0.0296(4) Uani 1 d . . .
H2 H 0.7594 0.6133 0.3670 0.036 Uiso 1 calc . . R
C1 C 0.74210(15) 0.3671(2) 0.54302(13) 0.0383(5) Uani 1 d . . .
H1 H 0.6823 0.4027 0.5586 0.046 Uiso 1 calc . . R
C2 C 0.80369(16) 0.2456(2) 0.59439(13) 0.0415(5) Uani 1 d . . .
H2A H 0.7855 0.2006 0.6429 0.050 Uiso 1 calc . . R
C3 C 0.88939(16) 0.1938(2) 0.57345(13) 0.0377(5) Uani 1 d . . .
H3 H 0.9317 0.1113 0.6071 0.045 Uiso 1 calc . . R
C4 C 0.91582(14) 0.26273(19) 0.50143(12) 0.0293(4) Uani 1 d . . .
C5 C 0.84835(13) 0.38319(19) 0.45330(11) 0.0255(4) Uani 1 d . . .
C6 C 0.86999(13) 0.45529(19) 0.37912(11) 0.0266(4) Uani 1 d . . .
C7 C 0.95601(14) 0.4081(2) 0.35499(12) 0.0317(4) Uani 1 d . . .
H7 H 0.9707 0.4562 0.3056 0.038 Uiso 1 calc . . R
C8 C 1.02235(14) 0.2881(2) 0.40361(13) 0.0352(5) Uani 1 d . . .
H8 H 1.0817 0.2561 0.3864 0.042 Uiso 1 calc . . R
C9 C 1.00364(14) 0.2170(2) 0.47446(12) 0.0338(4) Uani 1 d . . .
H9 H 1.0497 0.1362 0.5061 0.041 Uiso 1 calc . . R
C10 C 0.78160(14) 0.6349(2) 0.25272(12) 0.0277(4) Uani 1 d . . .
C11 C 0.68824(13) 0.74693(19) 0.22296(11) 0.0262(4) Uani 1 d . . .
C12 C 0.70792(15) 0.9061(2) 0.24051(12) 0.0314(4) Uani 1 d . . .
C13 C 0.62244(16) 1.0097(2) 0.21243(13) 0.0351(4) Uani 1 d . . .
H13 H 0.6347 1.1176 0.2246 0.042 Uiso 1 calc . . R
C14 C 0.52061(15) 0.9583(2) 0.16742(13) 0.0360(5) Uani 1 d . . .
H14 H 0.4634 1.0308 0.1492 0.043 Uiso 1 calc . . R
C15 C 0.50084(15) 0.8020(2) 0.14847(13) 0.0323(4) Uani 1 d . . .
H15 H 0.4304 0.7673 0.1168 0.039 Uiso 1 calc . . R
C16 C 0.58456(13) 0.69544(19) 0.17594(11) 0.0264(4) Uani 1 d . . .
C17 C 0.56302(14) 0.5276(2) 0.15420(12) 0.0277(4) Uani 1 d . . .
C18 C 0.43078(16) 0.3446(2) 0.07747(13) 0.0384(5) Uani 1 d . . .
H18A H 0.4405 0.2859 0.1340 0.046 Uiso 1 calc . . R
H18B H 0.4743 0.2945 0.0443 0.046 Uiso 1 calc . . R
C19 C 0.31523(16) 0.3462(2) 0.02055(14) 0.0448(5) Uani 1 d . . .
H19A H 0.3063 0.4081 -0.0340 0.067 Uiso 1 calc . . GR
H19B H 0.2727 0.3922 0.0550 0.067 Uiso 1 calc . . GR
H19C H 0.2910 0.2394 0.0034 0.067 Uiso 1 calc . . GR
C20 C 0.81938(16) 0.9666(2) 0.28707(15) 0.0454(5) Uani 1 d . . .
H20A H 0.8593 0.8910 0.3324 0.068 Uiso 1 calc . . GR
H20B H 0.8153 1.0658 0.3167 0.068 Uiso 1 calc . . GR
H20C H 0.8559 0.9824 0.2423 0.068 Uiso 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 C10 1.215(2) . ?
O2 C17 1.205(2) . ?
O3 C17 1.341(2) . ?
O3 C18 1.449(2) . ?
N1 C1 1.317(2) . ?
N1 C5 1.366(2) . ?
N2 H2 0.8800 . ?
N2 C6 1.406(2) . ?
N2 C10 1.355(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.405(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.353(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.413(3) . ?
C4 C5 1.413(2) . ?
C4 C9 1.414(2) . ?
C5 C6 1.424(2) . ?
C6 C7 1.371(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.406(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.357(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.515(2) . ?
C11 C12 1.402(2) . ?
C11 C16 1.401(2) . ?
C12 C13 1.393(3) . ?
C12 C20 1.509(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.393(2) . ?
C16 C17 1.488(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.498(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C17 O3 C18 116.13(14) . . ?
C1 N1 C5 117.25(16) . . ?
C6 N2 H2 116.0 . . ?
C10 N2 H2 116.0 . . ?
C10 N2 C6 127.94(14) . . ?
N1 C1 H1 117.9 . . ?
N1 C1 C2 124.19(18) . . ?
C2 C1 H1 117.9 . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 C1 118.78(18) . . ?
C3 C2 H2A 120.6 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.92(17) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 117.03(16) . . ?
C3 C4 C9 124.15(16) . . ?
C5 C4 C9 118.82(16) . . ?
N1 C5 C4 122.83(15) . . ?
N1 C5 C6 117.61(15) . . ?
C4 C5 C6 119.56(15) . . ?
N2 C6 C5 115.00(14) . . ?
C7 C6 N2 124.99(16) . . ?
C7 C6 C5 120.01(16) . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.70(17) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.65(16) . . ?
C9 C8 H8 119.2 . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.26(16) . . ?
C8 C9 H9 119.9 . . ?
O1 C10 N2 124.56(16) . . ?
O1 C10 C11 121.61(15) . . ?
N2 C10 C11 113.76(14) . . ?
C12 C11 C10 118.58(15) . . ?
C16 C11 C10 121.48(15) . . ?
C16 C11 C12 119.91(15) . . ?
C11 C12 C20 121.39(16) . . ?
C13 C12 C11 118.78(16) . . ?
C13 C12 C20 119.82(16) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.05(16) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.55(17) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.76(17) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C17 120.55(15) . . ?
C15 C16 C11 119.94(16) . . ?
C15 C16 C17 119.50(16) . . ?
O2 C17 O3 123.42(16) . . ?
O2 C17 C16 125.20(16) . . ?
O3 C17 C16 111.38(14) . . ?
O3 C18 H18A 110.3 . . ?
O3 C18 H18B 110.3 . . ?
O3 C18 C19 107.17(15) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C11 C12 -84.6(2) . . . . ?
O1 C10 C11 C16 93.1(2) . . . . ?
N1 C1 C2 C3 0.3(3) . . . . ?
N1 C5 C6 N2 0.1(2) . . . . ?
N1 C5 C6 C7 179.78(15) . . . . ?
N2 C6 C7 C8 179.80(16) . . . . ?
N2 C10 C11 C12 92.45(18) . . . . ?
N2 C10 C11 C16 -89.86(19) . . . . ?
C1 N1 C5 C4 -0.4(2) . . . . ?
C1 N1 C5 C6 179.64(16) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C2 C3 C4 C9 179.94(18) . . . . ?
C3 C4 C5 N1 1.0(2) . . . . ?
C3 C4 C5 C6 -179.00(15) . . . . ?
C3 C4 C9 C8 179.07(17) . . . . ?
C4 C5 C6 N2 -179.87(15) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 N1 C1 C2 -0.3(3) . . . . ?
C5 C4 C9 C8 0.0(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 N2 C10 O1 -10.4(3) . . . . ?
C6 N2 C10 C11 172.61(15) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C4 -0.1(3) . . . . ?
C9 C4 C5 N1 -179.90(16) . . . . ?
C9 C4 C5 C6 0.1(2) . . . . ?
C10 N2 C6 C5 -161.93(16) . . . . ?
C10 N2 C6 C7 18.4(3) . . . . ?
C10 C11 C12 C13 179.35(15) . . . . ?
C10 C11 C12 C20 0.6(2) . . . . ?
C10 C11 C16 C15 -179.07(15) . . . . ?
C10 C11 C16 C17 0.4(2) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C11 C16 C17 O2 9.9(3) . . . . ?
C11 C16 C17 O3 -170.62(15) . . . . ?
C12 C11 C16 C15 -1.4(2) . . . . ?
C12 C11 C16 C17 178.02(15) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C14 C15 C16 C17 -179.15(16) . . . . ?
C15 C16 C17 O2 -170.64(17) . . . . ?
C15 C16 C17 O3 8.8(2) . . . . ?
C16 C11 C12 C13 1.6(2) . . . . ?
C16 C11 C12 C20 -177.09(16) . . . . ?
C17 O3 C18 C19 175.14(15) . . . . ?
C18 O3 C17 O2 4.1(2) . . . . ?
C18 O3 C17 C16 -175.36(14) . . . . ?
C20 C12 C13 C14 178.00(17) . . . . ?

