# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_265
_database_code_depnum_ccdc_archive 'CCDC 1561983'
_audit_update_record             
;
2017-07-13 deposited with the CCDC.
2017-10-25 downloaded from the CCDC.
;
_audit_creation_date             2017-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N3 O2'
_chemical_formula_sum            'C16 H15 N3 O2'
_chemical_formula_weight         281.31
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0881(2)
_cell_length_b                   7.8709(4)
_cell_length_c                   14.5993(7)
_cell_angle_alpha                86.207(4)
_cell_angle_beta                 88.891(3)
_cell_angle_gamma                76.774(4)
_cell_volume                     679.53(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3460
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.2880
_cell_measurement_theta_min      5.7710
_shelx_estimated_absorpt_T_max   0.876
_shelx_estimated_absorpt_T_min   0.816
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4426
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.359
_diffrn_reflns_theta_min         5.786
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  30.00   1.00    1.00    --  -40.98  57.00 120.00   39
  2  ω    -31.00  -2.00   1.00    1.00    --  -40.98 125.00  60.00   29
  3  ω    -61.00 -31.00   1.00    1.00    --  -40.98  57.00 120.00   30
  4  ω    -68.00  32.00   1.00    1.00    --  -40.98  57.00   0.00  100
  5  ω    -94.00 -65.00   1.00    1.00    --  -40.98 125.00  60.00   29
  6  ω   -106.00 -22.00   1.00    1.00    --  -40.98 -57.00-150.00   84
  7  ω     32.00  67.00   1.00    1.00    --   40.98-125.00-180.00   35
  8  ω     45.00 133.00   1.00    1.00    --  106.95 -61.00-150.00   88
  9  ω     94.00 121.00   1.00    1.00    --  106.95 -30.00 -60.00   27
 10  ω     91.00 178.00   1.00    1.00    --  106.95  30.00 -60.00   87
 11  ω    128.00 172.00   1.00    1.00    --  106.95 125.00-180.00   44
 12  ω     33.00 135.00   1.00    1.00    --  106.95 -30.00 -30.00  102
 13  ω     96.00 121.00   1.00    1.00    --  106.95-125.00   0.00   25
 14  ω     58.00 109.00   1.00    1.00    --  106.95 -94.00 -30.00   51
 15  ω     47.00  74.00   1.00    1.00    --  106.95-125.00   0.00   27
 16  ω     32.00 132.00   1.00    1.00    --  106.95 -30.00 120.00  100
 17  ω     58.00 106.00   1.00    1.00    --  106.95-125.00 150.00   48
 18  ω     25.00  61.00   1.00    1.00    --  106.95 -94.00 150.00   36
 19  ω     31.00  66.00   1.00    1.00    --  106.95 -30.00 -60.00   35
 20  ω     43.00 107.00   1.00    1.00    --  106.95 -94.00-180.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0800946000
_diffrn_orient_matrix_UB_12      0.1450259000
_diffrn_orient_matrix_UB_13      0.0465763000
_diffrn_orient_matrix_UB_21      0.0852652000
_diffrn_orient_matrix_UB_22      0.0632536000
_diffrn_orient_matrix_UB_23      -0.0932866000
_diffrn_orient_matrix_UB_31      -0.2321309000
_diffrn_orient_matrix_UB_32      0.1247228000
_diffrn_orient_matrix_UB_33      -0.0176794000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2486
_reflns_number_total             2640
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         0.247
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2640
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.069
_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)+(0.0604P)²+0.1734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1077
_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:
 C12(H12), C13(H13), C11(H11), C15(H15), C6(H6), C8(H8), C3(H3), C4(H4), C7(H7)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C1(H1A,H1B,H1C)
;
_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
O2 O 0.71950(14) 0.78123(11) -0.09077(6) 0.0246(2) Uani 1 1 d . . . . .
O1 O 0.37672(15) 0.12744(13) 0.67817(6) 0.0302(2) Uani 1 1 d . . . . .
N1 N 0.62130(17) 0.35478(13) 0.33068(7) 0.0212(2) Uani 1 1 d . . . . .
N2 N 0.48006(16) 0.46915(13) 0.27523(7) 0.0215(2) Uani 1 1 d . . . . .
N3 N 0.83019(17) 0.29942(14) 0.29777(7) 0.0260(3) Uani 1 1 d . . . . .
C9 C 0.60515(19) 0.48968(15) 0.20072(8) 0.0205(3) Uani 1 1 d . . . . .
C10 C 0.51159(19) 0.60587(14) 0.12089(8) 0.0198(3) Uani 1 1 d . . . . .
C12 C 0.19417(19) 0.78567(15) 0.03904(8) 0.0229(3) Uani 1 1 d . . . . .
H12 H 0.039702 0.832788 0.035125 0.028 Uiso 1 1 calc R . . . .
C13 C 0.3350(2) 0.82661(15) -0.03114(8) 0.0214(3) Uani 1 1 d . . . . .
H13 H 0.275733 0.901172 -0.081183 0.026 Uiso 1 1 calc R . . . .
C5 C 0.5541(2) 0.29778(15) 0.41929(8) 0.0215(3) Uani 1 1 d . . . . .
C2 C 0.4229(2) 0.18878(16) 0.59208(8) 0.0237(3) Uani 1 1 d . . . . .
C11 C 0.2789(2) 0.67659(15) 0.11434(8) 0.0225(3) Uani 1 1 d . . . . .
H11 H 0.182170 0.650222 0.160425 0.027 Uiso 1 1 calc R . . . .
C15 C 0.65377(19) 0.64470(15) 0.05075(8) 0.0200(3) Uani 1 1 d . . . . .
H15 H 0.808201 0.597369 0.054603 0.024 Uiso 1 1 calc R . . . .
C6 C 0.7117(2) 0.18629(16) 0.47670(8) 0.0250(3) Uani 1 1 d . . . . .
H6 H 0.860338 0.148615 0.457384 0.030 Uiso 1 1 calc R . . . .
C14 C 0.5660(2) 0.75427(15) -0.02535(8) 0.0201(2) Uani 1 1 d . . . . .
C8 C 0.8217(2) 0.38405(16) 0.21529(8) 0.0253(3) Uani 1 1 d . . . . .
H8 H 0.941153 0.374427 0.173827 0.030 Uiso 1 1 calc R . . . .
C3 C 0.2658(2) 0.29894(17) 0.53413(9) 0.0266(3) Uani 1 1 d . . . . .
H3 H 0.117173 0.336925 0.553436 0.032 Uiso 1 1 calc R . . . .
C4 C 0.3320(2) 0.35188(16) 0.44730(9) 0.0264(3) Uani 1 1 d . . . . .
H4 H 0.226942 0.423764 0.407946 0.032 Uiso 1 1 calc R . . . .
C16 C 0.6354(2) 0.89711(16) -0.16857(8) 0.0249(3) Uani 1 1 d . . . . .
H16A H 0.758301 0.908020 -0.209007 0.037 Uiso 1 1 calc GR . . . .
H16B H 0.563468 1.009994 -0.148183 0.037 Uiso 1 1 calc GR . . . .
H16C H 0.527989 0.850908 -0.200621 0.037 Uiso 1 1 calc GR . . . .
C7 C 0.6448(2) 0.13241(17) 0.56248(8) 0.0265(3) Uani 1 1 d . . . . .
H7 H 0.749200 0.057596 0.600968 0.032 Uiso 1 1 calc R . . . .
C1 C 0.1515(2) 0.17759(19) 0.71057(9) 0.0319(3) Uani 1 1 d . . . . .
H1A H 0.053561 0.133917 0.672066 0.048 Uiso 1 1 calc GR . . . .
H1B H 0.105854 0.302837 0.709141 0.048 Uiso 1 1 calc GR . . . .
H1C H 0.142507 0.129953 0.772419 0.048 Uiso 1 1 calc GR . . . .


_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
O2 C14 1.3636(14) . ?
O2 C16 1.4340(13) . ?
O1 C2 1.3639(14) . ?
O1 C1 1.4185(15) . ?
N1 N2 1.3347(14) . ?
N1 N3 1.3373(14) . ?
N1 C5 1.4244(15) . ?
N2 C9 1.3380(15) . ?
N3 C8 1.3331(16) . ?
C9 C10 1.4715(16) . ?
C9 C8 1.4001(17) . ?
C10 C11 1.4010(16) . ?
C10 C15 1.3916(16) . ?
C12 H12 0.9300 . ?
C12 C13 1.3919(16) . ?
C12 C11 1.3807(17) . ?
C13 H13 0.9300 . ?
C13 C14 1.3935(16) . ?
C5 C6 1.3933(17) . ?
C5 C4 1.3838(17) . ?
C2 C3 1.3919(18) . ?
C2 C7 1.3920(17) . ?
C11 H11 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.3959(16) . ?
C6 H6 0.9300 . ?
C6 C7 1.3795(17) . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.3894(17) . ?
C4 H4 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C7 H7 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
C14 O2 C16 116.92(9) . . ?
C2 O1 C1 117.63(10) . . ?
N2 N1 N3 115.43(9) . . ?
N2 N1 C5 122.07(10) . . ?
N3 N1 C5 122.50(10) . . ?
N1 N2 C9 103.90(9) . . ?
C8 N3 N1 103.16(10) . . ?
N2 C9 C10 121.77(10) . . ?
N2 C9 C8 108.02(10) . . ?
C8 C9 C10 130.21(11) . . ?
C11 C10 C9 120.38(10) . . ?
C15 C10 C9 120.11(10) . . ?
C15 C10 C11 119.50(11) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.40(11) . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 119.05(11) . . ?
C14 C13 H13 120.5 . . ?
C6 C5 N1 119.80(11) . . ?
C4 C5 N1 119.72(11) . . ?
C4 C5 C6 120.48(11) . . ?
O1 C2 C3 124.78(12) . . ?
O1 C2 C7 115.50(11) . . ?
C3 C2 C7 119.72(11) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.59(11) . . ?
C12 C11 H11 120.2 . . ?
C10 C15 H15 119.8 . . ?
C10 C15 C14 120.41(11) . . ?
C14 C15 H15 119.8 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.29(11) . . ?
C7 C6 H6 120.4 . . ?
O2 C14 C13 124.34(11) . . ?
O2 C14 C15 115.63(10) . . ?
C13 C14 C15 120.03(11) . . ?
N3 C8 C9 109.49(11) . . ?
N3 C8 H8 125.3 . . ?
C9 C8 H8 125.3 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.69(12) . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.08(12) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.72(11) . . ?
C6 C7 H7 119.6 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.720
_oxdiff_exptl_absorpt_empirical_full_min 0.570
