# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_nbqbz3
_database_code_depnum_ccdc_archive 'CCDC 1421361'
_audit_update_record             
;
2015-08-30 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        N-(benzo[h]quinolin-10-yl)benzamide
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H14 N2 O'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            white

_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         298.33

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.9292(8)
_cell_length_b                   16.0839(11)
_cell_length_c                   8.7040(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.591(8)
_cell_angle_gamma                90.00
_cell_volume                     1487.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1011
_cell_measurement_theta_min      3.1680
_cell_measurement_theta_max      24.6310
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84517
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6356
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.1023
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         28.92
_reflns_number_total             3423
_reflns_number_gt                1483
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0227P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3423
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1655
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.001
_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
O O 0.56514(17) 0.06808(12) 0.3794(2) 0.0751(6) Uani 1 1 d . . .
N1 N 0.7583(2) 0.05119(12) 0.3223(3) 0.0504(6) Uani 1 1 d . . .
H1A H 0.813(2) 0.0126(14) 0.271(3) 0.079(9) Uiso 1 1 d . . .
N2 N 0.96200(19) -0.00338(12) 0.2447(3) 0.0529(6) Uani 1 1 d . . .
C1 C 0.5052(2) -0.09591(16) 0.2610(3) 0.0592(7) Uani 1 1 d . . .
H1B H 0.4747 -0.0827 0.3492 0.071 Uiso 1 1 calc R . .
C2 C 0.4626(3) -0.16619(18) 0.1731(4) 0.0739(9) Uani 1 1 d . . .
H2A H 0.4035 -0.2004 0.2028 0.089 Uiso 1 1 calc R . .
C3 C 0.5064(3) -0.18601(18) 0.0428(4) 0.0753(9) Uani 1 1 d . . .
H3A H 0.4780 -0.2338 -0.0147 0.090 Uiso 1 1 calc R . .
C4 C 0.5926(3) -0.13524(17) -0.0032(4) 0.0678(8) Uani 1 1 d . . .
H4A H 0.6211 -0.1479 -0.0930 0.081 Uiso 1 1 calc R . .
C5 C 0.6367(2) -0.06522(16) 0.0846(3) 0.0593(8) Uani 1 1 d . . .
H5A H 0.6959 -0.0313 0.0544 0.071 Uiso 1 1 calc R . .
C6 C 0.5936(2) -0.04528(15) 0.2168(3) 0.0490(7) Uani 1 1 d . . .
C7 C 0.6363(2) 0.03076(15) 0.3135(3) 0.0531(7) Uani 1 1 d . . .
C8 C 0.8304(2) 0.11581(14) 0.4075(3) 0.0488(7) Uani 1 1 d . . .
C9 C 0.7769(3) 0.17431(15) 0.4878(3) 0.0644(8) Uani 1 1 d . . .
H9A H 0.6915 0.1715 0.4857 0.077 Uiso 1 1 calc R . .
C10 C 0.8502(3) 0.23719(17) 0.5714(4) 0.0806(10) Uani 1 1 d . . .
H10A H 0.8134 0.2763 0.6251 0.097 Uiso 1 1 calc R . .
C11 C 0.9756(3) 0.24255(17) 0.5762(4) 0.0798(10) Uani 1 1 d . . .
H11A H 1.0232 0.2853 0.6328 0.096 Uiso 1 1 calc R . .
C12 C 1.0333(3) 0.18441(16) 0.4967(3) 0.0634(8) Uani 1 1 d . . .
C13 C 1.1645(3) 0.19108(19) 0.5005(4) 0.0804(10) Uani 1 1 d . . .
H13A H 1.2107 0.2339 0.5586 0.096 Uiso 1 1 calc R . .
C14 C 1.2233(3) 0.1381(2) 0.4237(4) 0.0804(10) Uani 1 1 d . . .
H14A H 1.3084 0.1452 0.4277 0.096 Uiso 1 1 calc R . .
C15 C 1.1565(3) 0.07126(17) 0.3362(4) 0.0588(7) Uani 1 1 d . . .
C16 C 1.2157(3) 0.0140(2) 0.2580(4) 0.0761(10) Uani 1 1 d . . .
H16A H 1.3009 0.0197 0.2612 0.091 Uiso 1 1 calc R . .
C17 C 1.1493(3) -0.05038(19) 0.1768(4) 0.0754(9) Uani 1 1 d . . .
H17A H 1.1884 -0.0893 0.1253 0.090 Uiso 1 1 calc R . .
C18 C 1.0223(3) -0.05646(16) 0.1730(3) 0.0632(8) Uani 1 1 d . . .
H18A H 0.9770 -0.1002 0.1169 0.076 Uiso 1 1 calc R . .
C19 C 1.0269(2) 0.06109(15) 0.3272(3) 0.0492(7) Uani 1 1 d . . .
C20 C 0.9619(2) 0.11912(14) 0.4084(3) 0.0481(7) 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
O C7 1.226(3) . ?
N1 C7 1.358(3) . ?
N1 C8 1.406(3) . ?
N1 H1A 1.03(2) . ?
N2 C18 1.321(3) . ?
N2 C19 1.362(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.386(3) . ?
C1 H1B 0.9300 . ?
C2 C3 1.369(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.379(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.496(3) . ?
C8 C9 1.381(3) . ?
C8 C20 1.436(3) . ?
C9 C10 1.386(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.364(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.398(4) . ?
C11 H11A 0.9300 . ?
C12 C20 1.421(3) . ?
C12 C13 1.431(4) . ?
C13 C14 1.336(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.417(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.391(4) . ?
C15 C19 1.410(3) . ?
C16 C17 1.363(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.384(3) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C20 1.453(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
C7 N1 C8 129.0(2) . . ?
C7 N1 H1A 119.2(13) . . ?
C8 N1 H1A 111.4(13) . . ?
C18 N2 C19 119.0(2) . . ?
C2 C1 C6 119.5(3) . . ?
C2 C1 H1B 120.2 . . ?
C6 C1 H1B 120.2 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 C7 122.5(2) . . ?
C1 C6 C7 118.0(2) . . ?
O C7 N1 125.3(2) . . ?
O C7 C6 121.0(2) . . ?
N1 C7 C6 113.7(2) . . ?
C9 C8 N1 121.3(2) . . ?
C9 C8 C20 120.9(2) . . ?
N1 C8 C20 117.8(2) . . ?
C8 C9 C10 120.1(3) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C11 C12 C20 120.5(3) . . ?
C11 C12 C13 120.3(3) . . ?
C20 C12 C13 119.2(3) . . ?
C14 C13 C12 122.5(3) . . ?
C14 C13 H13A 118.7 . . ?
C12 C13 H13A 118.7 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C16 C15 C19 118.2(3) . . ?
C16 C15 C14 121.7(3) . . ?
C19 C15 C14 120.1(3) . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C16 C17 C18 118.3(3) . . ?
C16 C17 H17A 120.8 . . ?
C18 C17 H17A 120.8 . . ?
N2 C18 C17 123.5(3) . . ?
N2 C18 H18A 118.3 . . ?
C17 C18 H18A 118.3 . . ?
N2 C19 C15 120.6(2) . . ?
N2 C19 C20 119.5(2) . . ?
C15 C19 C20 119.9(3) . . ?
C12 C20 C8 116.8(2) . . ?
C12 C20 C19 118.0(3) . . ?
C8 C20 C19 125.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.873
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036

