#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/80/7118021.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7118021
loop_
_publ_author_name
'Huan-Wei Tseng'
'Ta-Chun Lin'
'Chi-Lin Chen'
'Tzu-Chieh Lin'
'Yi-An Chen'
'Jun-Qi Liu'
'Cheng-Hsien Hung'
'Chi-Min Chao'
'Kuan-Miao Liu'
'Pi-Tai Chou'
_publ_section_title
;
 A new class of N-H proton transfer molecules: wide tautomer emission
 tuning from 590 nm to 770 nm via a facile, single site amino
 derivatization in 10-aminobenzo[h]quinoline
;
_journal_name_full               Chem.Commun.
_journal_page_first              16099
_journal_paper_doi               10.1039/C5cc06633F
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C20 H14 N2 O'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.33
_chemical_name_systematic        N-(benzo[h]quinolin-10-yl)benzamide
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-08-30 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.591(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9292(8)
_cell_length_b                   16.0839(11)
_cell_length_c                   8.7040(8)
_cell_measurement_reflns_used    1011
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      24.6310
_cell_measurement_theta_min      3.1680
_cell_volume                     1487.2(2)
_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_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_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_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.1023
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6356
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.92
_diffrn_reflns_theta_min         2.72
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84517
_exptl_absorpt_correction_type   multi-scan
_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_crystal_colour            white
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1655
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0227P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1395
_reflns_number_gt                1483
_reflns_number_total             3423
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc06633f2.cif
_cod_data_source_block           nbqbz3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7118021
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'
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 . . .
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'
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
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) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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) .
