# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_22aprbm
_database_code_depnum_ccdc_archive 'CCDC 1004473'
_audit_update_record             
;
2014-05-21 deposited with the CCDC.
2015-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N O2'
_chemical_formula_weight         275.29

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.159(5)
_cell_length_b                   9.364(5)
_cell_length_c                   10.541(5)
_cell_angle_alpha                78.846(5)
_cell_angle_beta                 82.356(5)
_cell_angle_gamma                72.557(5)
_cell_volume                     659.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1098
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      26.99

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3408
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2278
_reflns_number_gt                1712
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0992P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2278
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1585
_refine_ls_wR_factor_gt          0.1428
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2292(3) 0.2969(3) 0.4700(2) 0.0392(6) Uani 1 1 d . . .
H1 H 0.2443 0.3798 0.4091 0.047 Uiso 1 1 calc R . .
C2 C 0.1728(3) 0.3098(3) 0.5977(2) 0.0486(6) Uani 1 1 d . . .
H2 H 0.1509 0.4033 0.6236 0.058 Uiso 1 1 calc R . .
C3 C 0.1471(3) 0.1863(4) 0.6906(2) 0.0547(7) Uani 1 1 d . . .
H3 H 0.1081 0.2000 0.7762 0.066 Uiso 1 1 calc R . .
C4 C 0.1783(3) 0.0460(3) 0.6576(2) 0.0475(7) Uani 1 1 d . . .
H4 H 0.1602 -0.0350 0.7197 0.057 Uiso 1 1 calc R . .
C5 C 0.2387(3) 0.0269(3) 0.52719(18) 0.0375(6) Uani 1 1 d . . .
C6 C 0.2632(3) 0.1542(3) 0.43484(18) 0.0337(5) Uani 1 1 d . . .
C7 C 0.2853(3) -0.0967(3) 0.4581(2) 0.0377(5) Uani 1 1 d . . .
C8 C 0.3372(3) -0.0421(2) 0.33109(18) 0.0319(5) Uani 1 1 d . . .
C9 C 0.3922(3) -0.1584(2) 0.2507(2) 0.0339(5) Uani 1 1 d . . .
C10 C 0.3630(3) -0.3008(3) 0.3457(2) 0.0414(6) Uani 1 1 d . . .
C11 C 0.2931(3) -0.2610(3) 0.4802(2) 0.0442(6) Uani 1 1 d . . .
H11A H 0.1648 -0.2759 0.5085 0.053 Uiso 1 1 calc R . .
H11B H 0.3854 -0.3202 0.5433 0.053 Uiso 1 1 calc R . .
C12 C 0.3348(3) 0.2090(2) 0.19065(17) 0.0332(5) Uani 1 1 d . . .
H12A H 0.4300 0.1544 0.1296 0.040 Uiso 1 1 calc R . .
H12B H 0.3766 0.2949 0.2018 0.040 Uiso 1 1 calc R . .
C13 C 0.1354(3) 0.2650(2) 0.13692(17) 0.0295(5) Uani 1 1 d . . .
C14 C -0.0008(4) 0.3972(2) 0.1669(2) 0.0420(6) Uani 1 1 d . . .
H14 H 0.0338 0.4566 0.2158 0.050 Uiso 1 1 calc R . .
C15 C -0.1876(4) 0.4412(3) 0.1246(2) 0.0497(7) Uani 1 1 d . . .
H15 H -0.2783 0.5294 0.1458 0.060 Uiso 1 1 calc R . .
C16 C -0.2393(3) 0.3539(3) 0.0508(2) 0.0460(6) Uani 1 1 d . . .
H16 H -0.3650 0.3830 0.0228 0.055 Uiso 1 1 calc R . .
C17 C -0.1036(3) 0.2233(2) 0.0189(2) 0.0384(5) Uani 1 1 d . . .
H17 H -0.1379 0.1650 -0.0313 0.046 Uiso 1 1 calc R . .
C18 C 0.0830(3) 0.1792(2) 0.06145(18) 0.0327(5) Uani 1 1 d . . .
H18 H 0.1739 0.0915 0.0394 0.039 Uiso 1 1 calc R . .
N1 N 0.3281(2) 0.10854(19) 0.31590(15) 0.0315(4) Uani 1 1 d . . .
O1 O 0.4489(2) -0.15782(16) 0.13603(14) 0.0398(4) Uani 1 1 d . . .
O2 O 0.3929(2) -0.42222(19) 0.31173(18) 0.0559(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0275(11) 0.0624(15) 0.0345(11) -0.0119(10) -0.0039(9) -0.0198(10)
C2 0.0320(12) 0.0844(19) 0.0380(13) -0.0245(12) -0.0023(10) -0.0203(12)
C3 0.0303(12) 0.110(2) 0.0292(13) -0.0206(14) -0.0015(9) -0.0217(13)
C4 0.0271(12) 0.088(2) 0.0267(11) 0.0032(12) -0.0051(9) -0.0223(12)
C5 0.0246(10) 0.0647(15) 0.0255(11) 0.0017(10) -0.0065(8) -0.0199(10)
C6 0.0264(11) 0.0542(14) 0.0261(10) -0.0055(9) -0.0051(8) -0.0192(10)
C7 0.0252(11) 0.0551(14) 0.0344(11) 0.0065(10) -0.0107(8) -0.0188(10)
C8 0.0272(11) 0.0433(13) 0.0288(11) 0.0008(9) -0.0069(8) -0.0177(9)
C9 0.0259(11) 0.0387(13) 0.0368(12) 0.0030(9) -0.0098(9) -0.0112(9)
C10 0.0276(11) 0.0409(14) 0.0549(14) 0.0049(11) -0.0117(10) -0.0126(10)
C11 0.0306(12) 0.0571(15) 0.0430(13) 0.0182(11) -0.0125(10) -0.0222(11)
C12 0.0388(12) 0.0392(12) 0.0254(10) -0.0019(9) 0.0009(8) -0.0202(10)
C13 0.0337(11) 0.0323(11) 0.0212(9) 0.0003(8) 0.0027(8) -0.0126(9)
C14 0.0586(15) 0.0364(12) 0.0259(10) -0.0043(9) -0.0016(10) -0.0072(11)
C15 0.0510(15) 0.0456(14) 0.0323(12) 0.0024(10) 0.0038(10) 0.0082(11)
C16 0.0345(12) 0.0518(15) 0.0401(13) 0.0134(11) -0.0017(10) -0.0085(11)
C17 0.0413(13) 0.0355(12) 0.0384(12) 0.0056(9) -0.0090(9) -0.0158(10)
C18 0.0358(11) 0.0285(11) 0.0319(11) -0.0008(8) -0.0025(8) -0.0089(9)
N1 0.0324(9) 0.0424(11) 0.0234(9) -0.0010(7) -0.0038(7) -0.0180(8)
O1 0.0368(9) 0.0423(9) 0.0398(9) -0.0053(7) -0.0087(7) -0.0087(7)
O2 0.0413(10) 0.0402(10) 0.0814(13) 0.0016(9) -0.0042(8) -0.0121(8)

_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 C2 1.371(3) . ?
C1 C6 1.398(3) . ?
C2 C3 1.404(4) . ?
C3 C4 1.370(4) . ?
C4 C5 1.414(3) . ?
C5 C7 1.418(3) . ?
C5 C6 1.425(3) . ?
C6 N1 1.380(3) . ?
C7 C8 1.382(3) . ?
C7 C11 1.496(3) . ?
C8 N1 1.371(3) . ?
C8 C9 1.439(3) . ?
C9 O1 1.222(2) . ?
C9 C10 1.555(3) . ?
C10 O2 1.208(3) . ?
C10 C11 1.517(3) . ?
C12 N1 1.469(2) . ?
C12 C13 1.512(3) . ?
C13 C14 1.388(3) . ?
C13 C18 1.389(3) . ?
C14 C15 1.383(3) . ?
C15 C16 1.384(4) . ?
C16 C17 1.383(3) . ?
C17 C18 1.383(3) . ?

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 C6 117.4(2) . . ?
C1 C2 C3 122.1(2) . . ?
C4 C3 C2 121.3(2) . . ?
C3 C4 C5 118.7(2) . . ?
C4 C5 C7 134.9(2) . . ?
C4 C5 C6 118.9(2) . . ?
C7 C5 C6 106.21(18) . . ?
N1 C6 C1 129.33(19) . . ?
N1 C6 C5 108.92(19) . . ?
C1 C6 C5 121.72(19) . . ?
C8 C7 C5 106.7(2) . . ?
C8 C7 C11 113.3(2) . . ?
C5 C7 C11 140.04(19) . . ?
N1 C8 C7 111.08(19) . . ?
N1 C8 C9 136.77(17) . . ?
C7 C8 C9 112.1(2) . . ?
O1 C9 C8 132.58(19) . . ?
O1 C9 C10 124.1(2) . . ?
C8 C9 C10 103.33(18) . . ?
O2 C10 C11 127.6(2) . . ?
O2 C10 C9 122.5(2) . . ?
C11 C10 C9 109.96(19) . . ?
C7 C11 C10 101.27(17) . . ?
N1 C12 C13 110.78(15) . . ?
C14 C13 C18 119.1(2) . . ?
C14 C13 C12 121.30(18) . . ?
C18 C13 C12 119.57(18) . . ?
C15 C14 C13 120.6(2) . . ?
C14 C15 C16 119.9(2) . . ?
C17 C16 C15 119.9(2) . . ?
C16 C17 C18 120.1(2) . . ?
C17 C18 C13 120.38(19) . . ?
C8 N1 C6 107.08(16) . . ?
C8 N1 C12 125.07(16) . . ?
C6 N1 C12 126.00(17) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.067
