# Electronic Supplementary Material (ESI) for Analytical Methods.
# 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_gp_2_a
_database_code_depnum_ccdc_archive 'CCDC 1590339'
_audit_update_record             
;
2017-12-10 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;
_audit_creation_date             2017-03-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H20 N2 O'
_chemical_formula_sum            'C31 H20 N2 O'
_chemical_formula_weight         436.49
_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      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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.68(3)
_cell_length_b                   10.006(14)
_cell_length_c                   11.850(16)
_cell_angle_alpha                90
_cell_angle_beta                 101.871(16)
_cell_angle_gamma                90
_cell_volume                     2284(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    60
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.256
_cell_measurement_theta_min      1.057
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0891 before and 0.0678 after correction.
The Ratio of minimum to maximum transmission is 0.8590.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   SADABS
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             912.0
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.3928
_diffrn_reflns_av_unetI/netI     0.1975
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            44541
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        23.256
_diffrn_reflns_theta_max         23.256
_diffrn_reflns_theta_min         1.057
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'BRUKER APEX-II'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                820
_reflns_number_total             3239
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3118
_refine_ls_R_factor_gt           0.0838
_refine_ls_restrained_S_all      0.934
_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)+(0.1269P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.3095
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C25(H25), C24(H24), C18(H18), C31(H31), C10(H10), C15(H15),
 C14(H14), C30(H30), C28(H28), C4(H4), C5(H5), C11(H11), C26(H26), C13(H13),
 C27(H27), C6(H6), C8(H8), C12(H12), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N1 N 0.2648(5) 0.4341(9) 0.5294(7) 0.106(3) Uani 1 1 d . . . . .
C21 C 0.5040(6) 0.1320(9) 0.4043(8) 0.065(2) Uani 1 1 d . . . . .
N2 N 0.2917(5) 0.3387(9) 0.4614(7) 0.103(3) Uani 1 1 d . . . . .
C23 C 0.6169(6) 0.2212(11) 0.5004(9) 0.082(3) Uani 1 1 d . . . . .
C9 C 0.1324(6) 0.2586(11) 0.3827(12) 0.087(3) Uani 1 1 d . . . . .
O1 O 0.1587(4) 0.4558(8) 0.2860(7) 0.143(3) Uani 1 1 d . . . . .
C22 C 0.5766(7) 0.1284(9) 0.4249(8) 0.074(3) Uani 1 1 d . . . . .
C16 C 0.3954(6) 0.2241(9) 0.4375(7) 0.071(3) Uani 1 1 d . . . . .
C17 C 0.4684(6) 0.2253(9) 0.4604(7) 0.064(2) Uani 1 1 d . . . . .
C20 C 0.4643(7) 0.0380(10) 0.3257(8) 0.076(3) Uani 1 1 d . . . . .
C19 C 0.3926(8) 0.0425(9) 0.3051(7) 0.088(3) Uani 1 1 d . . . . .
H19 H 0.3669 -0.0181 0.2539 0.106 Uiso 1 1 calc R . . . .
C25 C 0.5108(6) 0.3184(9) 0.5390(7) 0.078(3) Uani 1 1 d . . . . .
H25 H 0.4895 0.3817 0.5776 0.094 Uiso 1 1 calc R . . . .
C24 C 0.5807(6) 0.3140(9) 0.5566(7) 0.081(3) Uani 1 1 d . . . . .
H24 H 0.6063 0.3745 0.6079 0.098 Uiso 1 1 calc R . . . .
C18 C 0.3587(5) 0.1347(10) 0.3589(8) 0.086(3) Uani 1 1 d . . . . .
H18 H 0.3104 0.1373 0.3424 0.104 Uiso 1 1 calc R . . . .
C31 C 0.5020(8) -0.0590(11) 0.2724(8) 0.094(3) Uani 1 1 d . . . . .
H31 H 0.4777 -0.1221 0.2221 0.112 Uiso 1 1 calc R . . . .
C2 C 0.2001(7) 0.4593(11) 0.4871(10) 0.091(3) Uani 1 1 d . . . . .
C29 C 0.6113(8) 0.0320(12) 0.3683(9) 0.091(3) Uani 1 1 d . . . . .
C10 C 0.1387(5) 0.1909(13) 0.4856(9) 0.098(3) Uani 1 1 d . . . . .
H10 H 0.1636 0.2282 0.5535 0.117 Uiso 1 1 calc R . . . .
C15 C 0.3573(6) 0.3218(9) 0.4945(8) 0.086(3) Uani 1 1 d . . . . .
H15 H 0.3815 0.3722 0.5557 0.103 Uiso 1 1 calc R . . . .
C14 C 0.0945(6) 0.2036(15) 0.2816(11) 0.109(4) Uani 1 1 d . . . . .
H14 H 0.0891 0.2505 0.2125 0.130 Uiso 1 1 calc R . . . .
C1 C 0.1641(6) 0.3924(13) 0.3764(11) 0.098(3) Uani 1 1 d . . . . .
C3 C 0.1627(7) 0.5570(10) 0.5437(12) 0.089(3) Uani 1 1 d . . . . .
C30 C 0.5713(9) -0.0594(11) 0.2942(10) 0.101(4) Uani 1 1 d . . . . .
H30 H 0.5938 -0.1234 0.2583 0.121 Uiso 1 1 calc R . . . .
C28 C 0.6848(8) 0.0313(12) 0.3926(11) 0.106(4) Uani 1 1 d . . . . .
H28 H 0.7083 -0.0327 0.3584 0.127 Uiso 1 1 calc R . . . .
C4 C 0.0950(8) 0.5910(12) 0.4952(10) 0.114(4) Uani 1 1 d . . . . .
H4 H 0.0735 0.5518 0.4258 0.137 Uiso 1 1 calc R . . . .
C5 C 0.0582(7) 0.6818(14) 0.5468(14) 0.123(4) Uani 1 1 d . . . . .
H5 H 0.0122 0.7012 0.5137 0.147 Uiso 1 1 calc R . . . .
C11 C 0.1076(7) 0.0667(14) 0.4872(12) 0.112(4) Uani 1 1 d . . . . .
H11 H 0.1110 0.0206 0.5563 0.134 Uiso 1 1 calc R . . . .
C26 C 0.6884(7) 0.2182(11) 0.5229(9) 0.109(4) Uani 1 1 d . . . . .
H26 H 0.7141 0.2777 0.5752 0.131 Uiso 1 1 calc R . . . .
C13 C 0.0650(7) 0.0790(17) 0.2843(12) 0.136(5) Uani 1 1 d . . . . .
H13 H 0.0404 0.0402 0.2168 0.163 Uiso 1 1 calc R . . . .
C27 C 0.7219(7) 0.1240(15) 0.4658(13) 0.125(4) Uani 1 1 d . . . . .
H27 H 0.7701 0.1242 0.4777 0.150 Uiso 1 1 calc R . . . .
C6 C 0.0899(9) 0.7431(12) 0.6472(15) 0.131(5) Uani 1 1 d . . . . .
H6 H 0.0664 0.8070 0.6813 0.158 Uiso 1 1 calc R . . . .
C8 C 0.1932(6) 0.6175(12) 0.6471(13) 0.115(4) Uani 1 1 d . . . . .
H8 H 0.2385 0.5959 0.6828 0.139 Uiso 1 1 calc R . . . .
C12 C 0.0721(6) 0.0133(12) 0.3871(16) 0.125(4) Uani 1 1 d . . . . .
H12 H 0.0521 -0.0707 0.3884 0.149 Uiso 1 1 calc R . . . .
C7 C 0.1565(9) 0.7090(12) 0.6965(11) 0.133(5) Uani 1 1 d . . . . .
H7 H 0.1776 0.7490 0.7657 0.159 Uiso 1 1 calc R . . . .


_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
N1 N2 1.419(10) . ?
N1 C2 1.294(10) . ?
C21 C22 1.400(12) . ?
C21 C17 1.412(11) . ?
C21 C20 1.437(12) . ?
N2 C15 1.282(10) . ?
C23 C22 1.414(11) . ?
C23 C24 1.417(12) . ?
C23 C26 1.379(12) . ?
C9 C10 1.378(12) . ?
C9 C14 1.388(12) . ?
C9 C1 1.485(13) . ?
O1 C1 1.231(10) . ?
C22 C29 1.427(12) . ?
C16 C17 1.406(11) . ?
C16 C18 1.384(11) . ?
C16 C15 1.477(12) . ?
C17 C25 1.453(11) . ?
C20 C19 1.382(12) . ?
C20 C31 1.444(13) . ?
C19 H19 0.9300 . ?
C19 C18 1.370(12) . ?
C25 H25 0.9300 . ?
C25 C24 1.349(10) . ?
C24 H24 0.9300 . ?
C18 H18 0.9300 . ?
C31 H31 0.9300 . ?
C31 C30 1.334(13) . ?
C2 C1 1.513(13) . ?
C2 C3 1.466(13) . ?
C29 C30 1.395(13) . ?
C29 C28 1.416(13) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(13) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.378(14) . ?
C3 C4 1.382(12) . ?
C3 C8 1.388(13) . ?
C30 H30 0.9300 . ?
C28 H28 0.9300 . ?
C28 C27 1.372(14) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(13) . ?
C5 H5 0.9300 . ?
C5 C6 1.369(14) . ?
C11 H11 0.9300 . ?
C11 C12 1.357(13) . ?
C26 H26 0.9300 . ?
C26 C27 1.401(13) . ?
C13 H13 0.9300 . ?
C13 C12 1.366(15) . ?
C27 H27 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.364(14) . ?
C8 H8 0.9300 . ?
C8 C7 1.370(13) . ?
C12 H12 0.9300 . ?
C7 H7 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
C2 N1 N2 111.2(10) . . ?
C22 C21 C17 121.5(10) . . ?
C22 C21 C20 119.7(11) . . ?
C17 C21 C20 118.8(11) . . ?
C15 N2 N1 112.6(9) . . ?
C22 C23 C24 117.2(10) . . ?
C26 C23 C22 121.7(11) . . ?
C26 C23 C24 121.0(12) . . ?
C10 C9 C14 120.2(11) . . ?
C10 C9 C1 121.7(13) . . ?
C14 C9 C1 118.1(12) . . ?
C21 C22 C23 120.9(10) . . ?
C21 C22 C29 120.4(12) . . ?
C23 C22 C29 118.7(13) . . ?
C17 C16 C15 120.1(10) . . ?
C18 C16 C17 120.5(9) . . ?
C18 C16 C15 119.4(11) . . ?
C21 C17 C25 116.8(10) . . ?
C16 C17 C21 119.3(10) . . ?
C16 C17 C25 123.9(10) . . ?
C21 C20 C31 117.6(11) . . ?
C19 C20 C21 119.5(11) . . ?
C19 C20 C31 122.9(13) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 C20 121.1(10) . . ?
C18 C19 H19 119.4 . . ?
C17 C25 H25 119.6 . . ?
C24 C25 C17 120.7(9) . . ?
C24 C25 H25 119.6 . . ?
C23 C24 H24 118.5 . . ?
C25 C24 C23 123.0(10) . . ?
C25 C24 H24 118.5 . . ?
C16 C18 H18 119.6 . . ?
C19 C18 C16 120.8(10) . . ?
C19 C18 H18 119.6 . . ?
C20 C31 H31 119.5 . . ?
C30 C31 C20 121.0(12) . . ?
C30 C31 H31 119.5 . . ?
N1 C2 C1 119.9(11) . . ?
N1 C2 C3 119.9(12) . . ?
C3 C2 C1 120.1(12) . . ?
C30 C29 C22 118.4(13) . . ?
C30 C29 C28 123.1(14) . . ?
C28 C29 C22 118.5(12) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(10) . . ?
C11 C10 H10 120.2 . . ?
N2 C15 C16 121.5(10) . . ?
N2 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C9 C14 H14 120.2 . . ?
C13 C14 C9 119.5(12) . . ?
C13 C14 H14 120.2 . . ?
C9 C1 C2 118.8(11) . . ?
O1 C1 C9 123.1(12) . . ?
O1 C1 C2 117.9(11) . . ?
C4 C3 C2 120.4(14) . . ?
C4 C3 C8 117.7(11) . . ?
C8 C3 C2 121.9(13) . . ?
C31 C30 C29 122.8(13) . . ?
C31 C30 H30 118.6 . . ?
C29 C30 H30 118.6 . . ?
C29 C28 H28 119.6 . . ?
C27 C28 C29 120.8(12) . . ?
C27 C28 H28 119.6 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.8(12) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(14) . . ?
C6 C5 H5 120.2 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.3(11) . . ?
C12 C11 H11 120.3 . . ?
C23 C26 H26 120.5 . . ?
C23 C26 C27 118.9(12) . . ?
C27 C26 H26 120.5 . . ?
C14 C13 H13 120.3 . . ?
C12 C13 C14 119.3(13) . . ?
C12 C13 H13 120.3 . . ?
C28 C27 C26 121.3(13) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.1(14) . . ?
C7 C6 H6 120.5 . . ?
C3 C8 H8 120.1 . . ?
C7 C8 C3 119.9(12) . . ?
C7 C8 H8 120.1 . . ?
C11 C12 C13 122.0(13) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C6 C7 C8 122.0(13) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#
_vrf_RINTA01_gp_2_a              
;
PROBLEM:  The value of Rint is greater than 0.25
            Rint given   0.393
RESPONSE: The crystal was poorly diffracting at higher Bragg angles.
The situation did not improve even after recrystallisation and fresh data
collection.
;
#
_vrf_PLAT020_gp_2_a              
;
PROBLEM:  The value of Rint is greater than 0.12 .........      0.393 Report
RESPONSE: Weakly diffracting crystal resulting in relatively high
Rint appears to be responsible for poor data to parameter ratio. 
;
# end Validation Reply Form
