# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_rnv27
_database_code_depnum_ccdc_archive 'CCDC 1579961'
_audit_update_record             
;
2017-10-13 deposited with the CCDC.
2017-12-06 downloaded from the CCDC.
;
_audit_creation_date             2017-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N3 O'
_chemical_formula_sum            'C18 H15 N3 O'
_chemical_formula_weight         289.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 h15 N3 o1'
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      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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.5664(3)
_cell_length_b                   8.8236(5)
_cell_length_c                   28.6221(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1405.79(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1643
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.2370
_cell_measurement_theta_min      3.6780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            6244
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.712
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   96.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   38.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   59.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000   30.0000 66

#__ type_ start__ end____ width___ exp.time_
  3 omega  -49.00  -23.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   17.00   45.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000  -60.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0153893000
_diffrn_orient_matrix_UB_12      0.0349351000
_diffrn_orient_matrix_UB_13      0.0221246000
_diffrn_orient_matrix_UB_21      0.0190845000
_diffrn_orient_matrix_UB_22      0.0720688000
_diffrn_orient_matrix_UB_23      -0.0103322000
_diffrn_orient_matrix_UB_31      -0.1250313000
_diffrn_orient_matrix_UB_32      0.0066889000
_diffrn_orient_matrix_UB_33      -0.0042744000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.595
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.854
_reflns_number_gt                2693
_reflns_number_total             3043
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 903 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.070
_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)+(0.0425P)²+0.1573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0924
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C17(H17), C16(H16), C2(H2), C8(H8), C7(H7), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.1437(3) 0.5334(2) 0.78803(6) 0.0206(4) Uani 1 1 d . . . . .
N2 N 1.4466(3) 1.1451(2) 0.90593(6) 0.0154(4) Uani 1 1 d . . . . .
N3 N 0.9497(3) 0.8959(2) 0.90027(6) 0.0135(4) Uani 1 1 d . . . . .
C13 C 0.5307(4) 0.7493(3) 0.86867(8) 0.0147(5) Uani 1 1 d . . . . .
H13 H 0.5458 0.7708 0.9003 0.018 Uiso 1 1 calc R . . . .
C12 C 0.6940(4) 0.8126(3) 0.83737(7) 0.0136(5) Uani 1 1 d . . . . .
C14 C 0.3461(4) 0.6550(3) 0.85388(8) 0.0149(5) Uani 1 1 d . . . . .
H14 H 0.2399 0.6136 0.8755 0.018 Uiso 1 1 calc R . . . .
N1 N 1.2047(4) 1.0941(2) 0.83818(6) 0.0168(4) Uani 1 1 d . . . . .
C3 C 1.2596(4) 1.0763(3) 0.88304(8) 0.0146(5) Uani 1 1 d . . . . .
C1 C 0.8921(4) 0.9090(3) 0.85450(7) 0.0140(5) Uani 1 1 d . . . . .
C17 C 0.6658(4) 0.7773(3) 0.78970(8) 0.0167(5) Uani 1 1 d . . . . .
H17 H 0.7719 0.8180 0.7680 0.020 Uiso 1 1 calc R . . . .
C15 C 0.3211(4) 0.6229(3) 0.80675(8) 0.0154(5) Uani 1 1 d . . . . .
C10 C 1.1353(4) 0.9797(3) 0.91431(7) 0.0130(5) Uani 1 1 d . . . . .
C11 C 1.6136(4) 1.2533(3) 0.88576(8) 0.0193(5) Uani 1 1 d . . . . .
H11A H 1.5937 1.3499 0.9007 0.029 Uiso 1 1 calc GR . . . .
H11B H 1.5822 1.2633 0.8529 0.029 Uiso 1 1 calc GR . . . .
H11C H 1.7751 1.2183 0.8903 0.029 Uiso 1 1 calc GR . . . .
C9 C 1.2590(4) 0.9891(3) 0.95845(8) 0.0141(5) Uani 1 1 d . . . . .
C18 C -0.0125(5) 0.4563(3) 0.81958(8) 0.0202(6) Uani 1 1 d . . . . .
H18A H -0.1002 0.5291 0.8377 0.030 Uiso 1 1 calc GR . . . .
H18B H 0.0807 0.3932 0.8400 0.030 Uiso 1 1 calc GR . . . .
H18C H -0.1230 0.3946 0.8022 0.030 Uiso 1 1 calc GR . . . .
C16 C 0.4830(5) 0.6833(3) 0.77471(8) 0.0178(5) Uani 1 1 d . . . . .
H16 H 0.4681 0.6603 0.7431 0.021 Uiso 1 1 calc R . . . .
C2 C 1.0191(4) 1.0075(3) 0.82468(8) 0.0166(5) Uani 1 1 d . . . . .
H2 H 0.9711 1.0129 0.7936 0.020 Uiso 1 1 calc R . . . .
C8 C 1.2310(4) 0.9179(3) 1.00176(8) 0.0171(5) Uani 1 1 d . . . . .
H8 H 1.1046 0.8511 1.0070 0.021 Uiso 1 1 calc R . . . .
C4 C 1.4504(4) 1.0910(3) 0.95153(8) 0.0150(5) Uani 1 1 d . . . . .
C7 C 1.3959(4) 0.9492(3) 1.03664(8) 0.0198(5) Uani 1 1 d . . . . .
H7 H 1.3814 0.9016 1.0655 0.024 Uiso 1 1 calc R . . . .
C6 C 1.5846(4) 1.0516(3) 1.02911(8) 0.0204(5) Uani 1 1 d . . . . .
H6 H 1.6918 1.0714 1.0533 0.024 Uiso 1 1 calc R . . . .
C5 C 1.6153(4) 1.1241(3) 0.98663(8) 0.0171(5) Uani 1 1 d . . . . .
H5 H 1.7406 1.1920 0.9818 0.021 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 C15 1.373(3) . ?
O1 C18 1.426(3) . ?
N2 C3 1.372(3) . ?
N2 C11 1.452(3) . ?
N2 C4 1.390(3) . ?
N3 C1 1.354(3) . ?
N3 C10 1.332(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.393(3) . ?
C13 C14 1.388(3) . ?
C12 C1 1.477(3) . ?
C12 C17 1.408(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
N1 C3 1.329(3) . ?
N1 C2 1.342(3) . ?
C3 C10 1.417(3) . ?
C1 C2 1.408(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.381(4) . ?
C15 C16 1.392(3) . ?
C10 C9 1.441(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C9 C8 1.399(3) . ?
C9 C4 1.408(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C16 H16 0.9300 . ?
C2 H2 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.384(3) . ?
C4 C5 1.392(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.402(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.385(3) . ?
C5 H5 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
C15 O1 C18 117.75(18) . . ?
C3 N2 C11 125.91(19) . . ?
C3 N2 C4 107.95(19) . . ?
C4 N2 C11 126.1(2) . . ?
C10 N3 C1 115.35(19) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C14 C13 C12 121.8(2) . . ?
C13 C12 C1 120.3(2) . . ?
C13 C12 C17 117.5(2) . . ?
C17 C12 C1 122.2(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C3 N1 C2 112.8(2) . . ?
N2 C3 C10 109.58(19) . . ?
N1 C3 N2 125.7(2) . . ?
N1 C3 C10 124.7(2) . . ?
N3 C1 C12 116.7(2) . . ?
N3 C1 C2 121.4(2) . . ?
C2 C1 C12 121.94(19) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.0(2) . . ?
C16 C17 H17 119.5 . . ?
O1 C15 C14 124.7(2) . . ?
O1 C15 C16 115.4(2) . . ?
C14 C15 C16 119.9(2) . . ?
N3 C10 C3 121.5(2) . . ?
N3 C10 C9 131.8(2) . . ?
C3 C10 C9 106.6(2) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C9 C10 134.3(2) . . ?
C8 C9 C4 119.7(2) . . ?
C4 C9 C10 105.98(19) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
N1 C2 C1 124.3(2) . . ?
N1 C2 H2 117.9 . . ?
C1 C2 H2 117.9 . . ?
C9 C8 H8 120.8 . . ?
C7 C8 C9 118.4(2) . . ?
C7 C8 H8 120.8 . . ?
N2 C4 C9 109.9(2) . . ?
N2 C4 C5 128.0(2) . . ?
C5 C4 C9 122.1(2) . . ?
C8 C7 H7 119.5 . . ?
C8 C7 C6 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
C7 C6 H6 119.2 . . ?
C5 C6 C7 121.7(2) . . ?
C5 C6 H6 119.2 . . ?
C4 C5 H5 121.4 . . ?
C6 C5 C4 117.1(2) . . ?
C6 C5 H5 121.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C15 C16 C17 178.7(2) . . . . ?
N2 C3 C10 N3 -178.0(2) . . . . ?
N2 C3 C10 C9 -1.2(2) . . . . ?
N2 C4 C5 C6 -178.0(2) . . . . ?
N3 C1 C2 N1 0.6(4) . . . . ?
N3 C10 C9 C8 -0.7(4) . . . . ?
N3 C10 C9 C4 176.5(2) . . . . ?
C13 C12 C1 N3 19.1(3) . . . . ?
C13 C12 C1 C2 -162.2(2) . . . . ?
C13 C12 C17 C16 -0.1(3) . . . . ?
C13 C14 C15 O1 -178.9(2) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C12 C1 C2 N1 -178.0(2) . . . . ?
C12 C17 C16 C15 0.7(4) . . . . ?
C14 C13 C12 C1 -178.3(2) . . . . ?
C14 C13 C12 C17 -0.1(3) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
N1 C3 C10 N3 0.7(4) . . . . ?
N1 C3 C10 C9 177.5(2) . . . . ?
C3 N2 C4 C9 -1.7(2) . . . . ?
C3 N2 C4 C5 176.9(2) . . . . ?
C3 N1 C2 C1 0.7(3) . . . . ?
C3 C10 C9 C8 -177.1(2) . . . . ?
C3 C10 C9 C4 0.1(2) . . . . ?
C1 N3 C10 C3 0.7(3) . . . . ?
C1 N3 C10 C9 -175.2(2) . . . . ?
C1 C12 C17 C16 178.1(2) . . . . ?
C17 C12 C1 N3 -159.0(2) . . . . ?
C17 C12 C1 C2 19.7(3) . . . . ?
C10 N3 C1 C12 177.40(19) . . . . ?
C10 N3 C1 C2 -1.3(3) . . . . ?
C10 C9 C8 C7 176.3(2) . . . . ?
C10 C9 C4 N2 0.9(2) . . . . ?
C10 C9 C4 C5 -177.7(2) . . . . ?
C11 N2 C3 N1 2.1(4) . . . . ?
C11 N2 C3 C10 -179.2(2) . . . . ?
C11 N2 C4 C9 179.3(2) . . . . ?
C11 N2 C4 C5 -2.1(4) . . . . ?
C9 C8 C7 C6 1.0(4) . . . . ?
C9 C4 C5 C6 0.4(3) . . . . ?
C18 O1 C15 C14 -6.3(3) . . . . ?
C18 O1 C15 C16 173.8(2) . . . . ?
C2 N1 C3 N2 177.1(2) . . . . ?
C2 N1 C3 C10 -1.3(3) . . . . ?
C8 C9 C4 N2 178.6(2) . . . . ?
C8 C9 C4 C5 0.0(3) . . . . ?
C8 C7 C6 C5 -0.7(4) . . . . ?
C4 N2 C3 N1 -176.9(2) . . . . ?
C4 N2 C3 C10 1.7(2) . . . . ?
C4 C9 C8 C7 -0.6(3) . . . . ?
C7 C6 C5 C4 0.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
