# 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_CX11
_database_code_depnum_ccdc_archive 'CCDC 1581141'
_audit_update_record             
;
2017-10-20 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;
_audit_creation_date             2017-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        CX11
_chemical_formula_moiety         'C25 H15 N O2'
_chemical_formula_sum            'C25 H15 N O2'
_chemical_formula_weight         361.38
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.4892(8)
_cell_length_b                   7.8471(4)
_cell_length_c                   15.5804(9)
_cell_angle_alpha                90
_cell_angle_beta                 114.831(7)
_cell_angle_gamma                90
_cell_volume                     1718.65(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1454
_cell_measurement_temperature    153(7)
_cell_measurement_theta_max      61.1650
_cell_measurement_theta_min      5.2640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4112
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        62.677
_diffrn_reflns_theta_max         62.677
_diffrn_reflns_theta_min         3.376
_diffrn_ambient_temperature      153(7)
_diffrn_detector_area_resol_mean 16.0855
_diffrn_measured_fraction_theta_full 0.9663
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -5.00  101.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -       34.3979   19.0000  -90.0000 106

#__ type_ start__ end____ width___ exp.time_
  2 omega   21.00  103.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -       34.3979   57.0000  -30.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega   17.00   83.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -       88.6885  -94.0000 -150.0000 66

#__ type_ start__ end____ width___ exp.time_
  4 omega   21.00   66.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -       88.6885  -30.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega   20.00   59.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -       88.6885  -30.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega   65.00  159.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -       88.6885   45.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega   57.00   83.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -       88.6885  -94.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   69.00  158.00   1.0000  104.0000
omega____ theta____ kappa____ phi______ frames
    -       88.6885   45.0000   90.0000 89
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0715452000
_diffrn_orient_matrix_UB_12      -0.1038834000
_diffrn_orient_matrix_UB_13      0.0835761000
_diffrn_orient_matrix_UB_21      0.0745923000
_diffrn_orient_matrix_UB_22      0.0185737000
_diffrn_orient_matrix_UB_23      -0.0407777000
_diffrn_orient_matrix_UB_31      0.0364365000
_diffrn_orient_matrix_UB_32      0.1654686000
_diffrn_orient_matrix_UB_33      0.0567675000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2129
_reflns_number_total             2531
_reflns_odcompleteness_completeness 96.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.107
_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)+(0.0427P)²+0.0609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0959
_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:
 C11(H11), C9(H9), C24(H24), C15(H15), C12(H12), C2(H2), C5(H5), C18(H18),
 C21(H21), C23(H23), C22(H22), C17(H17), C16(H16), C4(H4), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.88627(8) 0.52723(17) 0.54995(8) 0.0350(3) Uani 1 1 d . . . . .
O2 O 0.62858(8) 0.75604(17) 0.48849(8) 0.0391(3) Uani 1 1 d . . . . .
N1 N 0.76058(9) 0.56525(18) 0.83564(9) 0.0282(3) Uani 1 1 d . . . . .
C14 C 0.81051(12) 0.6456(2) 0.92294(11) 0.0281(4) Uani 1 1 d . . . . .
C10 C 0.79071(12) 0.5528(2) 0.76100(11) 0.0278(4) Uani 1 1 d . . . . .
C11 C 0.87739(12) 0.4755(2) 0.77689(11) 0.0305(4) Uani 1 1 d . . . . .
H11 H 0.9151 0.4302 0.8360 0.037 Uiso 1 1 calc R . . . .
C6 C 0.75560(12) 0.7034(2) 0.44478(11) 0.0294(4) Uani 1 1 d . . . . .
C25 C 0.67079(11) 0.5202(2) 0.82877(11) 0.0276(4) Uani 1 1 d . . . . .
C8 C 0.76403(11) 0.6118(2) 0.59988(11) 0.0276(4) Uani 1 1 d . . . . .
C20 C 0.66337(12) 0.5672(2) 0.91229(11) 0.0299(4) Uani 1 1 d . . . . .
C9 C 0.73450(11) 0.6182(2) 0.67305(11) 0.0274(4) Uani 1 1 d . . . . .
H9 H 0.6762 0.6671 0.6623 0.033 Uiso 1 1 calc R . . . .
C13 C 0.85061(12) 0.5360(2) 0.61735(11) 0.0289(4) Uani 1 1 d . . . . .
C24 C 0.59755(12) 0.4366(2) 0.75567(12) 0.0324(4) Uani 1 1 d . . . . .
H24 H 0.6026 0.4079 0.7001 0.039 Uiso 1 1 calc R . . . .
C1 C 0.84092(12) 0.6167(2) 0.46717(11) 0.0315(4) Uani 1 1 d . . . . .
C15 C 0.90100(12) 0.7163(2) 0.96005(11) 0.0335(4) Uani 1 1 d . . . . .
H15 H 0.9397 0.7103 0.9279 0.040 Uiso 1 1 calc R . . . .
C12 C 0.90712(12) 0.4662(2) 0.70509(11) 0.0322(4) Uani 1 1 d . . . . .
H12 H 0.9644 0.4137 0.7153 0.039 Uiso 1 1 calc R . . . .
C7 C 0.70770(11) 0.6949(2) 0.50866(11) 0.0285(4) Uani 1 1 d . . . . .
C19 C 0.75213(12) 0.6493(2) 0.97185(11) 0.0298(4) Uani 1 1 d . . . . .
C2 C 0.88604(13) 0.6184(3) 0.40664(12) 0.0400(5) Uani 1 1 d . . . . .
H2 H 0.9421 0.5577 0.4216 0.048 Uiso 1 1 calc R . . . .
C5 C 0.71790(13) 0.7982(2) 0.36100(11) 0.0347(4) Uani 1 1 d . . . . .
H5 H 0.6617 0.8588 0.3453 0.042 Uiso 1 1 calc R . . . .
C18 C 0.78529(14) 0.7278(2) 1.06013(12) 0.0369(4) Uani 1 1 d . . . . .
H18 H 0.7480 0.7301 1.0939 0.044 Uiso 1 1 calc R . . . .
C21 C 0.58049(13) 0.5274(3) 0.92302(13) 0.0382(4) Uani 1 1 d . . . . .
H21 H 0.5742 0.5579 0.9778 0.046 Uiso 1 1 calc R . . . .
C23 C 0.51675(12) 0.3976(2) 0.76867(13) 0.0390(4) Uani 1 1 d . . . . .
H23 H 0.4670 0.3403 0.7212 0.047 Uiso 1 1 calc R . . . .
C22 C 0.50843(13) 0.4424(3) 0.85151(14) 0.0430(5) Uani 1 1 d . . . . .
H22 H 0.4534 0.4144 0.8584 0.052 Uiso 1 1 calc R . . . .
C17 C 0.87400(14) 0.8018(2) 1.09660(12) 0.0411(5) Uani 1 1 d . . . . .
H17 H 0.8963 0.8562 1.1550 0.049 Uiso 1 1 calc R . . . .
C16 C 0.93106(13) 0.7962(2) 1.04701(12) 0.0387(5) Uani 1 1 d . . . . .
H16 H 0.9907 0.8474 1.0731 0.046 Uiso 1 1 calc R . . . .
C4 C 0.76324(14) 0.8027(3) 0.30154(12) 0.0420(5) Uani 1 1 d . . . . .
H4 H 0.7381 0.8669 0.2463 0.050 Uiso 1 1 calc R . . . .
C3 C 0.84665(14) 0.7108(3) 0.32457(13) 0.0445(5) Uani 1 1 d . . . . .
H3 H 0.8763 0.7121 0.2836 0.053 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
O1 C13 1.378(2) . ?
O1 C1 1.374(2) . ?
O2 C7 1.228(2) . ?
N1 C14 1.401(2) . ?
N1 C10 1.427(2) . ?
N1 C25 1.395(2) . ?
C14 C15 1.388(2) . ?
C14 C19 1.406(2) . ?
C10 C11 1.397(2) . ?
C10 C9 1.377(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(2) . ?
C6 C1 1.394(2) . ?
C6 C7 1.472(2) . ?
C6 C5 1.399(2) . ?
C25 C20 1.403(2) . ?
C25 C24 1.389(2) . ?
C8 C9 1.396(2) . ?
C8 C13 1.386(2) . ?
C8 C7 1.471(2) . ?
C20 C19 1.448(2) . ?
C20 C21 1.398(3) . ?
C9 H9 0.9300 . ?
C13 C12 1.389(2) . ?
C24 H24 0.9300 . ?
C24 C23 1.383(3) . ?
C1 C2 1.390(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(3) . ?
C12 H12 0.9300 . ?
C19 C18 1.393(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.378(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.376(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.374(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.395(3) . ?
C22 H22 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.398(3) . ?
C16 H16 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.389(3) . ?
C3 H3 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
C1 O1 C13 118.63(13) . . ?
C14 N1 C10 125.88(14) . . ?
C25 N1 C14 108.35(13) . . ?
C25 N1 C10 125.23(13) . . ?
N1 C14 C19 108.48(14) . . ?
C15 C14 N1 129.32(15) . . ?
C15 C14 C19 122.18(15) . . ?
C11 C10 N1 120.27(14) . . ?
C9 C10 N1 119.94(15) . . ?
C9 C10 C11 119.80(15) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.17(15) . . ?
C12 C11 H11 119.9 . . ?
C1 C6 C7 120.20(15) . . ?
C1 C6 C5 118.25(16) . . ?
C5 C6 C7 121.55(16) . . ?
N1 C25 C20 109.24(14) . . ?
C24 C25 N1 128.86(15) . . ?
C24 C25 C20 121.86(16) . . ?
C9 C8 C7 120.54(15) . . ?
C13 C8 C9 118.48(15) . . ?
C13 C8 C7 120.82(15) . . ?
C25 C20 C19 106.62(14) . . ?
C21 C20 C25 119.30(16) . . ?
C21 C20 C19 134.07(16) . . ?
C10 C9 C8 120.80(15) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
O1 C13 C8 122.43(14) . . ?
O1 C13 C12 116.20(14) . . ?
C8 C13 C12 121.37(15) . . ?
C25 C24 H24 121.2 . . ?
C23 C24 C25 117.52(17) . . ?
C23 C24 H24 121.2 . . ?
O1 C1 C6 122.77(15) . . ?
O1 C1 C2 115.93(16) . . ?
C2 C1 C6 121.30(16) . . ?
C14 C15 H15 121.5 . . ?
C16 C15 C14 117.04(17) . . ?
C16 C15 H15 121.5 . . ?
C11 C12 C13 119.36(15) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
O2 C7 C6 122.81(15) . . ?
O2 C7 C8 122.94(15) . . ?
C8 C7 C6 114.23(14) . . ?
C14 C19 C20 107.28(14) . . ?
C18 C19 C14 119.32(16) . . ?
C18 C19 C20 133.38(16) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.98(18) . . ?
C3 C2 H2 120.5 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.64(17) . . ?
C4 C5 H5 119.7 . . ?
C19 C18 H18 120.5 . . ?
C17 C18 C19 118.98(17) . . ?
C17 C18 H18 120.5 . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.05(17) . . ?
C22 C21 H21 120.5 . . ?
C24 C23 H23 119.3 . . ?
C24 C23 C22 121.36(17) . . ?
C22 C23 H23 119.3 . . ?
C21 C22 C23 120.90(18) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C18 C17 H17 119.6 . . ?
C18 C17 C16 120.82(16) . . ?
C16 C17 H17 119.6 . . ?
C15 C16 C17 121.63(17) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.65(17) . . ?
C3 C4 H4 120.2 . . ?
C2 C3 C4 121.14(17) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
