# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1546115'
_audit_update_record             
;
2017-04-26 deposited with the CCDC.
2018-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H28 N4 O2'
_chemical_formula_sum            'C27 H28 N4 O2'
_chemical_formula_weight         440.53

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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

_cell_length_a                   22.679(7)
_cell_length_b                   10.176(3)
_cell_length_c                   21.562(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.879(4)
_cell_angle_gamma                90
_cell_volume                     4958(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1089
_cell_measurement_theta_min      2.366
_cell_measurement_theta_max      19.376

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6941
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14327
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.802
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4364
_reflns_number_gt                2456
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+2.3114P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00174(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4364
_refine_ls_number_parameters     300
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.02051(8) -0.13070(16) 0.05577(7) 0.0739(5) Uani 1 1 d . . . . .
O2 O 0.06319(7) 0.08806(17) 0.20232(6) 0.0747(5) Uani 1 1 d . . . . .
N1 N 0.10136(8) 0.15177(17) 0.11449(7) 0.0541(5) Uani 1 1 d . . . . .
N2 N -0.06828(11) 0.3827(2) 0.23182(13) 0.1048(9) Uani 1 1 d . . . . .
N3 N -0.05720(8) 0.3190(2) 0.19148(11) 0.0670(5) Uani 1 1 d . U . . .
N4 N -0.04287(9) 0.2609(2) 0.14559(9) 0.0709(6) Uani 1 1 d . U . . .
C1 C -0.23106(12) 0.0285(3) 0.08189(13) 0.0835(8) Uani 1 1 d . U . . .
H1 H -0.2703 0.0112 0.0683 0.100 Uiso 1 1 calc R U . . .
C2 C -0.21030(12) -0.0001(3) 0.14162(13) 0.0836(7) Uani 1 1 d . U . . .
H2 H -0.2354 -0.0373 0.1687 0.100 Uiso 1 1 calc R U . . .
C3 C -0.15223(11) 0.0261(2) 0.16192(11) 0.0697(6) Uani 1 1 d . U . . .
H3 H -0.1386 0.0068 0.2028 0.084 Uiso 1 1 calc R U . . .
C4 C -0.11383(10) 0.0806(2) 0.12249(9) 0.0541(5) Uani 1 1 d . U . . .
C5 C -0.13517(11) 0.1087(2) 0.06174(10) 0.0642(6) Uani 1 1 d . U . . .
H5 H -0.1102 0.1449 0.0343 0.077 Uiso 1 1 calc R U . . .
C6 C -0.19381(12) 0.0829(3) 0.04200(12) 0.0779(7) Uani 1 1 d . U . . .
H6 H -0.2080 0.1026 0.0013 0.093 Uiso 1 1 calc R U . . .
C7 C -0.05113(9) 0.1142(2) 0.14747(9) 0.0534(6) Uani 1 1 d . U . . .
H7 H -0.0445 0.0838 0.1906 0.064 Uiso 1 1 calc R U . . .
C8 C -0.00152(9) 0.0623(2) 0.11022(8) 0.0508(6) Uani 1 1 d . . . . .
H8 H -0.0047 0.1040 0.0691 0.061 Uiso 1 1 calc R U . . .
C9 C 0.00107(10) -0.0870(2) 0.10197(9) 0.0549(6) Uani 1 1 d . . . . .
C10 C -0.01819(13) -0.1738(2) 0.15228(11) 0.0798(8) Uani 1 1 d . . . . .
H10A H -0.0611 -0.1724 0.1505 0.096 Uiso 1 1 calc R U . . .
H10B H -0.0034 -0.1373 0.1921 0.096 Uiso 1 1 calc R U . . .
C11 C 0.00201(15) -0.3166(3) 0.14951(13) 0.0946(9) Uani 1 1 d . . . . .
H11A H -0.0196 -0.3686 0.1777 0.114 Uiso 1 1 calc R U . . .
H11B H -0.0076 -0.3499 0.1077 0.114 Uiso 1 1 calc R U . . .
C12 C 0.06691(17) -0.3331(3) 0.16645(17) 0.1343(13) Uani 1 1 d . . . . .
H12A H 0.0886 -0.2901 0.1359 0.201 Uiso 1 1 calc R U . . .
H12B H 0.0766 -0.4249 0.1677 0.201 Uiso 1 1 calc R U . . .
H12C H 0.0772 -0.2948 0.2066 0.201 Uiso 1 1 calc R U . . .
C13 C 0.05743(10) 0.1030(2) 0.14552(9) 0.0544(6) Uani 1 1 d . . . . .
C14 C 0.10441(10) 0.1500(2) 0.04685(9) 0.0593(6) Uani 1 1 d . . . . .
H14A H 0.0682 0.1118 0.0276 0.071 Uiso 1 1 calc R U . . .
H14B H 0.1369 0.0939 0.0372 0.071 Uiso 1 1 calc R U . . .
C15 C 0.15613(10) 0.1890(2) 0.15093(10) 0.0630(6) Uani 1 1 d . . . . .
H15A H 0.1462 0.2265 0.1901 0.076 Uiso 1 1 calc R U . . .
H15B H 0.1757 0.2568 0.1286 0.076 Uiso 1 1 calc R U . . .
C16 C 0.19904(10) 0.0767(2) 0.16461(9) 0.0575(6) Uani 1 1 d . . . . .
C17 C 0.18684(12) -0.0509(3) 0.14722(12) 0.0777(7) Uani 1 1 d . . . . .
H17 H 0.1504 -0.0712 0.1264 0.093 Uiso 1 1 calc R U . . .
C18 C 0.22778(14) -0.1497(3) 0.16010(14) 0.0925(9) Uani 1 1 d . . . . .
H18 H 0.2189 -0.2355 0.1476 0.111 Uiso 1 1 calc R U . . .
C19 C 0.28112(14) -0.1217(4) 0.19105(13) 0.0901(9) Uani 1 1 d . . . . .
H19 H 0.3087 -0.1883 0.1997 0.108 Uiso 1 1 calc R U . . .
C20 C 0.29417(12) 0.0037(4) 0.20934(13) 0.0879(9) Uani 1 1 d . . . . .
H20 H 0.3305 0.0226 0.2307 0.106 Uiso 1 1 calc R U . . .
C21 C 0.25353(11) 0.1028(3) 0.19622(11) 0.0748(7) Uani 1 1 d . . . . .
H21 H 0.2628 0.1883 0.2088 0.090 Uiso 1 1 calc R U . . .
C22 C 0.11278(10) 0.2835(2) 0.01881(9) 0.0540(6) Uani 1 1 d . . . . .
C23 C 0.15331(12) 0.2986(3) -0.02468(11) 0.0771(8) Uani 1 1 d . . . . .
H23 H 0.1759 0.2270 -0.0352 0.093 Uiso 1 1 calc R U . . .
C24 C 0.16088(15) 0.4183(3) -0.05294(13) 0.0960(9) Uani 1 1 d . . . . .
H24 H 0.1888 0.4270 -0.0819 0.115 Uiso 1 1 calc R U . . .
C25 C 0.12787(15) 0.5230(3) -0.03873(14) 0.0932(9) Uani 1 1 d . . . . .
H25 H 0.1324 0.6031 -0.0585 0.112 Uiso 1 1 calc R U . . .
C26 C 0.08785(14) 0.5106(3) 0.00473(15) 0.0956(9) Uani 1 1 d . . . . .
H26 H 0.0655 0.5828 0.0151 0.115 Uiso 1 1 calc R U . . .
C27 C 0.08050(11) 0.3909(3) 0.03336(12) 0.0789(8) Uani 1 1 d . . . . .
H27 H 0.0532 0.3833 0.0630 0.095 Uiso 1 1 calc R U . . .


_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 C9 1.208(2) . ?
O2 C13 1.230(2) . ?
N1 C13 1.342(3) . ?
N1 C15 1.462(3) . ?
N1 C14 1.466(2) . ?
N2 N3 1.130(3) . ?
N3 N4 1.220(3) . ?
N4 C7 1.506(3) . ?
C1 C2 1.364(4) . ?
C1 C6 1.372(4) . ?
C2 C3 1.378(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.387(3) . ?
C4 C7 1.516(3) . ?
C5 C6 1.386(3) . ?
C7 C8 1.531(3) . ?
C8 C9 1.531(3) . ?
C8 C13 1.538(3) . ?
C9 C10 1.493(3) . ?
C10 C11 1.526(3) . ?
C11 C12 1.496(4) . ?
C14 C22 1.505(3) . ?
C15 C16 1.514(3) . ?
C16 C17 1.374(3) . ?
C16 C21 1.385(3) . ?
C17 C18 1.380(3) . ?
C18 C19 1.361(4) . ?
C19 C20 1.360(4) . ?
C20 C21 1.379(4) . ?
C22 C27 1.367(3) . ?
C22 C23 1.376(3) . ?
C23 C24 1.379(3) . ?
C24 C25 1.352(4) . ?
C25 C26 1.365(4) . ?
C26 C27 1.382(4) . ?

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
C13 N1 C15 117.44(17) . . ?
C13 N1 C14 126.27(17) . . ?
C15 N1 C14 115.33(17) . . ?
N2 N3 N4 173.8(3) . . ?
N3 N4 C7 114.61(19) . . ?
C2 C1 C6 119.7(3) . . ?
C1 C2 C3 120.2(3) . . ?
C2 C3 C4 121.1(2) . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 C7 119.50(19) . . ?
C5 C4 C7 122.0(2) . . ?
C6 C5 C4 120.0(2) . . ?
C1 C6 C5 120.6(2) . . ?
N4 C7 C4 109.22(17) . . ?
N4 C7 C8 103.24(17) . . ?
C4 C7 C8 116.41(16) . . ?
C7 C8 C9 116.12(17) . . ?
C7 C8 C13 107.13(16) . . ?
C9 C8 C13 106.50(16) . . ?
O1 C9 C10 122.1(2) . . ?
O1 C9 C8 118.78(19) . . ?
C10 C9 C8 119.10(18) . . ?
C9 C10 C11 115.3(2) . . ?
C12 C11 C10 113.0(3) . . ?
O2 C13 N1 121.5(2) . . ?
O2 C13 C8 118.27(19) . . ?
N1 C13 C8 120.26(17) . . ?
N1 C14 C22 114.02(17) . . ?
N1 C15 C16 114.32(18) . . ?
C17 C16 C21 117.8(2) . . ?
C17 C16 C15 123.3(2) . . ?
C21 C16 C15 118.9(2) . . ?
C16 C17 C18 121.1(3) . . ?
C19 C18 C17 120.0(3) . . ?
C20 C19 C18 120.1(3) . . ?
C19 C20 C21 120.1(3) . . ?
C20 C21 C16 120.9(3) . . ?
C27 C22 C23 118.0(2) . . ?
C27 C22 C14 122.7(2) . . ?
C23 C22 C14 119.3(2) . . ?
C22 C23 C24 121.0(3) . . ?
C25 C24 C23 120.2(3) . . ?
C24 C25 C26 119.8(3) . . ?
C25 C26 C27 120.0(3) . . ?
C22 C27 C26 121.0(3) . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.031

