# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_cu_2017553_0m
_database_code_depnum_ccdc_archive 'CCDC 1835950'
_audit_update_record             
;
2018-04-10 deposited with the CCDC.
2018-05-07 downloaded from the CCDC.
;
_audit_creation_date             2017-07-05
_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         'C15 H11 N O'
_chemical_formula_sum            'C15 H11 N O'
_chemical_formula_weight         221.25
_chemical_absolute_configuration rmad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.4849(5)
_cell_length_b                   7.9199(6)
_cell_length_c                   21.9097(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1125.28(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    205
_cell_measurement_theta_max      70.17
_cell_measurement_theta_min      4.04
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1131 before and 0.0437 after correction. The Ratio of minimum to maximum transmission is 0.8990. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12229
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         4.035
_diffrn_ambient_temperature      205
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                1918
_reflns_number_total             1930
_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       ?
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 758 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1930
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.096
_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)+(0.0341P)²+0.1661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0677
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C6(H6), C17(H17), C8(H8), C7(H7), C14(H14), C15(H15), C16(H16)
;
_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
O11 O -0.09289(19) 0.72290(18) 0.38945(6) 0.0469(4) Uani 1 1 d . . . . .
N5 N 0.3547(2) 0.67340(17) 0.44963(6) 0.0301(3) Uani 1 1 d . . . . .
C3 C 0.4915(2) 0.40441(19) 0.44266(7) 0.0271(3) Uani 1 1 d . . . . .
C4 C 0.4986(3) 0.5754(2) 0.46842(7) 0.0307(4) Uani 1 1 d . . . . .
H4 H 0.6001 0.6100 0.4964 0.037 Uiso 1 1 calc R . . . .
C2 C 0.3208(2) 0.4020(2) 0.40426(7) 0.0255(3) Uani 1 1 d . . . . .
C1 C 0.2273(2) 0.5761(2) 0.40510(7) 0.0263(4) Uani 1 1 d . . . . .
C13 C 0.2219(3) 0.6713(2) 0.34505(7) 0.0288(4) Uani 1 1 d . . . . .
C9 C 0.6111(3) 0.2616(2) 0.45185(8) 0.0343(4) Uani 1 1 d . . . . .
H9 H 0.7267 0.2647 0.4777 0.041 Uiso 1 1 calc R . . . .
C6 C 0.2646(3) 0.2545(2) 0.37487(8) 0.0346(4) Uani 1 1 d . . . . .
H6 H 0.1487 0.2514 0.3491 0.042 Uiso 1 1 calc R . . . .
C12 C 0.0360(3) 0.7559(2) 0.34139(8) 0.0361(4) Uani 1 1 d . . . . .
C10 C -0.0020(3) 0.5834(2) 0.42248(8) 0.0338(4) Uani 1 1 d . . . . .
H10A H -0.0706 0.4775 0.4115 0.041 Uiso 1 1 calc R . . . .
H10B H -0.0171 0.6007 0.4665 0.041 Uiso 1 1 calc R . . . .
C17 C 0.3688(3) 0.6914(2) 0.30024(8) 0.0399(4) Uani 1 1 d . . . . .
H17 H 0.4959 0.6346 0.3026 0.048 Uiso 1 1 calc R . . . .
C8 C 0.5561(3) 0.1147(2) 0.42196(8) 0.0394(4) Uani 1 1 d . . . . .
H8 H 0.6358 0.0166 0.4271 0.047 Uiso 1 1 calc R . . . .
C7 C 0.3837(3) 0.1110(2) 0.38431(8) 0.0411(4) Uani 1 1 d . . . . .
H7 H 0.3469 0.0096 0.3649 0.049 Uiso 1 1 calc R . . . .
C14 C -0.0097(4) 0.8643(3) 0.29372(10) 0.0517(5) Uani 1 1 d . . . . .
H14 H -0.1358 0.9225 0.2918 0.062 Uiso 1 1 calc R . . . .
C15 C 0.1391(4) 0.8828(3) 0.24907(10) 0.0577(6) Uani 1 1 d . . . . .
H15 H 0.1130 0.9555 0.2161 0.069 Uiso 1 1 calc R . . . .
C16 C 0.3246(4) 0.7979(3) 0.25137(9) 0.0542(6) Uani 1 1 d . . . . .
H16 H 0.4215 0.8120 0.2199 0.065 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
O11 C12 1.370(2) . ?
O11 C10 1.446(2) . ?
N5 C4 1.282(2) . ?
N5 C1 1.493(2) . ?
C3 C4 1.468(2) . ?
C3 C2 1.391(2) . ?
C3 C9 1.386(2) . ?
C4 H4 0.9400 . ?
C2 C1 1.506(2) . ?
C2 C6 1.383(2) . ?
C1 C13 1.517(2) . ?
C1 C10 1.537(2) . ?
C13 C12 1.381(2) . ?
C13 C17 1.378(2) . ?
C9 H9 0.9400 . ?
C9 C8 1.382(3) . ?
C6 H6 0.9400 . ?
C6 C7 1.389(3) . ?
C12 C14 1.384(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C17 H17 0.9400 . ?
C17 C16 1.393(3) . ?
C8 H8 0.9400 . ?
C8 C7 1.390(3) . ?
C7 H7 0.9400 . ?
C14 H14 0.9400 . ?
C14 C15 1.382(3) . ?
C15 H15 0.9400 . ?
C15 C16 1.379(4) . ?
C16 H16 0.9400 . ?

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
C12 O11 C10 106.37(13) . . ?
C4 N5 C1 107.46(13) . . ?
C2 C3 C4 105.70(14) . . ?
C9 C3 C4 132.77(15) . . ?
C9 C3 C2 121.48(15) . . ?
N5 C4 C3 114.36(15) . . ?
N5 C4 H4 122.8 . . ?
C3 C4 H4 122.8 . . ?
C3 C2 C1 107.46(13) . . ?
C6 C2 C3 120.21(15) . . ?
C6 C2 C1 132.31(15) . . ?
N5 C1 C2 104.96(12) . . ?
N5 C1 C13 108.86(13) . . ?
N5 C1 C10 110.75(13) . . ?
C2 C1 C13 116.98(13) . . ?
C2 C1 C10 115.30(14) . . ?
C13 C1 C10 99.99(13) . . ?
C12 C13 C1 108.17(14) . . ?
C17 C13 C1 131.27(15) . . ?
C17 C13 C12 120.41(16) . . ?
C3 C9 H9 120.9 . . ?
C8 C9 C3 118.25(15) . . ?
C8 C9 H9 120.9 . . ?
C2 C6 H6 120.8 . . ?
C2 C6 C7 118.37(15) . . ?
C7 C6 H6 120.8 . . ?
O11 C12 C13 113.29(15) . . ?
O11 C12 C14 124.61(18) . . ?
C13 C12 C14 122.09(19) . . ?
O11 C10 C1 107.43(14) . . ?
O11 C10 H10A 110.2 . . ?
O11 C10 H10B 110.2 . . ?
C1 C10 H10A 110.2 . . ?
C1 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C13 C17 H17 120.8 . . ?
C13 C17 C16 118.39(19) . . ?
C16 C17 H17 120.8 . . ?
C9 C8 H8 119.8 . . ?
C9 C8 C7 120.44(16) . . ?
C7 C8 H8 119.8 . . ?
C6 C7 C8 121.23(17) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C12 C14 H14 121.6 . . ?
C15 C14 C12 116.8(2) . . ?
C15 C14 H14 121.6 . . ?
C14 C15 H15 118.9 . . ?
C16 C15 C14 122.12(19) . . ?
C16 C15 H15 118.9 . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
