# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shaw32
_database_code_depnum_ccdc_archive 'CCDC 1555026'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-09-26 downloaded from the CCDC.
;
_audit_creation_date             2017-06-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H11 N O'
_chemical_formula_sum            'C18 H11 N O'
_chemical_formula_weight         257.28
_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 0.0150 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   21.6561(6)
_cell_length_b                   5.31660(10)
_cell_length_c                   22.9403(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.0740(10)
_cell_angle_gamma                90
_cell_volume                     2411.53(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.629
_cell_measurement_theta_min      3.673
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.7018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1054 before and 0.0431 after correction. The Ratio of minimum to maximum transmission is 0.9334. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            gold
_exptl_crystal_colour_primary    gold
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            38376
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.604
_diffrn_reflns_theta_min         3.672
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2617
_reflns_number_total             2769
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.0177(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0627P)²+1.0577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1057
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.31730(5) 0.45453(19) 0.14349(5) 0.0263(2) Uani 1 1 d . . . . .
H1 H 0.3465 0.5952 0.1506 0.032 Uiso 1 1 calc R . . . .
C2 C 0.26780(5) 0.4050(2) 0.08309(5) 0.0289(2) Uani 1 1 d . . . . .
H2 H 0.2630 0.5138 0.0487 0.035 Uiso 1 1 calc R . . . .
C3 C 0.22482(5) 0.1967(2) 0.07220(5) 0.0293(2) Uani 1 1 d . . . . .
H3 H 0.1918 0.1659 0.0303 0.035 Uiso 1 1 calc R . . . .
C4 C 0.22926(5) 0.03437(19) 0.12111(5) 0.0284(2) Uani 1 1 d . . . . .
H4 H 0.1999 -0.1062 0.1135 0.034 Uiso 1 1 calc R . . . .
C4A C 0.27862(5) 0.08590(18) 0.18200(5) 0.0253(2) Uani 1 1 d . . . . .
N5 N 0.29231(4) -0.03691(17) 0.23929(4) 0.0277(2) Uani 1 1 d . . . . .
H5 H 0.2748(7) -0.186(3) 0.2433(7) 0.041(4) Uiso 1 1 d . . . . .
C5A C 0.34653(5) 0.07932(18) 0.28760(5) 0.0249(2) Uani 1 1 d . . . . .
C6 C 0.37754(5) 0.01491(19) 0.35261(5) 0.0267(2) Uani 1 1 d . . . . .
H6 H 0.3619 -0.1245 0.3687 0.032 Uiso 1 1 calc R . . . .
C7 C 0.43139(5) 0.15907(19) 0.39266(5) 0.0268(2) Uani 1 1 d . . . . .
H7 H 0.4533 0.1189 0.4368 0.032 Uiso 1 1 calc R . . . .
C7A C 0.45351(5) 0.36534(18) 0.36777(4) 0.0246(2) Uani 1 1 d . . . . .
C8 C 0.55830(5) 0.5956(2) 0.45448(5) 0.0296(2) Uani 1 1 d . . . . .
H8 H 0.5623 0.4957 0.4902 0.036 Uiso 1 1 calc R . . . .
C8A C 0.50804(5) 0.54619(18) 0.39389(5) 0.0252(2) Uani 1 1 d . . . . .
C9 C 0.60230(5) 0.7949(2) 0.46115(5) 0.0324(2) Uani 1 1 d . . . . .
H9 H 0.6365 0.8321 0.5021 0.039 Uiso 1 1 calc R . . . .
C10 C 0.59728(5) 0.9415(2) 0.40886(5) 0.0312(2) Uani 1 1 d . . . . .
H10 H 0.6283 1.0756 0.4149 0.037 Uiso 1 1 calc R . . . .
C11 C 0.54765(5) 0.89509(19) 0.34794(5) 0.0279(2) Uani 1 1 d . . . . .
H11 H 0.5439 0.9937 0.3121 0.034 Uiso 1 1 calc R . . . .
C11A C 0.50417(5) 0.69746(19) 0.34261(5) 0.0250(2) Uani 1 1 d . . . . .
O12 O 0.45096(3) 0.62516(13) 0.28639(3) 0.02502(19) Uani 1 1 d . . . . .
C13 C 0.42134(5) 0.42429(18) 0.30295(4) 0.0232(2) Uani 1 1 d . . . . .
C14 C 0.36675(5) 0.28602(18) 0.26085(4) 0.0237(2) Uani 1 1 d . . . . .
C15 C 0.32321(5) 0.29321(18) 0.19352(4) 0.0240(2) Uani 1 1 d . . . . .


_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
C1 H1 0.9500 . ?
C1 C2 1.3879(13) . ?
C1 C15 1.3962(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.4021(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3875(15) . ?
C4 H4 0.9500 . ?
C4 C4A 1.3967(13) . ?
C4A N5 1.3869(13) . ?
C4A C15 1.4174(13) . ?
N5 H5 0.901(16) . ?
N5 C5A 1.3883(12) . ?
C5A C6 1.4054(13) . ?
C5A C14 1.4125(13) . ?
C6 H6 0.9500 . ?
C6 C7 1.3846(14) . ?
C7 H7 0.9500 . ?
C7 C7A 1.4076(14) . ?
C7A C8A 1.4494(13) . ?
C7A C13 1.3964(13) . ?
C8 H8 0.9500 . ?
C8 C8A 1.3969(13) . ?
C8 C9 1.3913(15) . ?
C8A C11A 1.3990(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.3972(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.3942(14) . ?
C11 H11 0.9500 . ?
C11 C11A 1.3827(14) . ?
C11A O12 1.3879(11) . ?
O12 C13 1.3766(11) . ?
C13 C14 1.3926(13) . ?
C14 C15 1.4449(13) . ?

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 C1 H1 120.7 . . ?
C2 C1 C15 118.60(9) . . ?
C15 C1 H1 120.7 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.93(10) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.68(9) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C4A 117.33(9) . . ?
C4A C4 H4 121.3 . . ?
C4 C4A C15 121.62(9) . . ?
N5 C4A C4 129.49(9) . . ?
N5 C4A C15 108.87(8) . . ?
C4A N5 H5 125.2(9) . . ?
C4A N5 C5A 109.34(8) . . ?
C5A N5 H5 124.4(9) . . ?
N5 C5A C6 128.39(9) . . ?
N5 C5A C14 108.10(8) . . ?
C6 C5A C14 123.50(9) . . ?
C5A C6 H6 120.7 . . ?
C7 C6 C5A 118.53(9) . . ?
C7 C6 H6 120.7 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C7A 119.74(9) . . ?
C7A C7 H7 120.1 . . ?
C7 C7A C8A 134.75(9) . . ?
C13 C7A C7 120.15(9) . . ?
C13 C7A C8A 105.05(8) . . ?
C8A C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C9 C8 C8A 118.26(10) . . ?
C8 C8A C7A 135.13(9) . . ?
C8 C8A C11A 118.93(9) . . ?
C11A C8A C7A 105.94(8) . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.37(9) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.33(10) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 121.9 . . ?
C11A C11 C10 116.24(9) . . ?
C11A C11 H11 121.9 . . ?
C11 C11A C8A 123.88(9) . . ?
C11 C11A O12 124.75(9) . . ?
O12 C11A C8A 111.37(8) . . ?
C13 O12 C11A 105.20(7) . . ?
O12 C13 C7A 112.44(8) . . ?
O12 C13 C14 125.28(8) . . ?
C14 C13 C7A 122.25(9) . . ?
C5A C14 C15 107.59(8) . . ?
C13 C14 C5A 115.80(8) . . ?
C13 C14 C15 136.59(9) . . ?
C1 C15 C4A 119.83(9) . . ?
C1 C15 C14 134.10(9) . . ?
C4A C15 C14 106.06(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
