#------------------------------------------------------------------------------
#$Date: 2019-10-28 05:04:12 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219650 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/44/4514461.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_4514461
loop_
_publ_author_name
'Liu, Huapeng'
'Lu, Zhuoqun'
'Ye, Kaiqi'
'Zhang, Zuolun'
'Zhang, Hongyu'
_publ_section_title
;
 Polymorph-Dependent Luminescence Response to Acid Vapors and Its
 Application in Safety Protection of File Information.
;
_journal_issue                   37
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              34526
_journal_page_last               34531
_journal_paper_doi               10.1021/acsami.9b14474
_journal_volume                  11
_journal_year                    2019
_chemical_formula_moiety         'C17 H13 N O'
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.06(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.091(2)
_cell_length_b                   14.151(3)
_cell_length_c                   7.3872(15)
_cell_measurement_reflns_used    8359
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      3.11
_cell_volume                     1263.9(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12169
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         3.111
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0521
_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)+(0.0811P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1425
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1831
_reflns_number_total             2871
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am9b14474_si_002.cif
_cod_data_source_block           2
_cod_database_code               4514461
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.38488(11) 0.78959(10) 0.2240(2) 0.0398(4) Uani 1 1 d . .
O1 O 0.51306(10) 0.64946(9) 0.2861(2) 0.0523(4) Uani 1 1 d . .
H100 H 0.4555 0.6770 0.2605 0.078 Uiso 1 1 calc R U
C3 C 0.46584(13) 0.84539(12) 0.2655(2) 0.0364(4) Uani 1 1 d . .
C4 C 0.65922(12) 0.87385(12) 0.3750(2) 0.0345(4) Uani 1 1 d . .
C5 C 0.28281(12) 0.82655(11) 0.1624(2) 0.0352(4) Uani 1 1 d . .
C6 C 0.57186(12) 0.81016(11) 0.3221(2) 0.0344(4) Uani 1 1 d . .
C7 C 0.64544(14) 0.97272(13) 0.3886(2) 0.0423(4) Uani 1 1 d . .
C8 C 0.76452(13) 0.83635(13) 0.4215(2) 0.0406(4) Uani 1 1 d . .
C9 C 0.59118(13) 0.71257(12) 0.3253(2) 0.0389(4) Uani 1 1 d . .
C10 C 0.27470(14) 0.90606(12) 0.0524(2) 0.0397(4) Uani 1 1 d . .
C11 C 0.77986(15) 0.73684(14) 0.4147(3) 0.0502(5) Uani 1 1 d . .
C12 C 0.18665(14) 0.77844(13) 0.2120(3) 0.0412(4) Uani 1 1 d . .
C13 C 0.69746(16) 0.67750(14) 0.3701(3) 0.0487(5) Uani 1 1 d . .
C14 C 0.17157(15) 0.93816(13) -0.0028(3) 0.0456(4) Uani 1 1 d . .
C15 C 0.07701(15) 0.89093(14) 0.0495(3) 0.0489(5) Uani 1 1 d . .
C16 C 0.84979(15) 0.89801(16) 0.4785(3) 0.0525(5) Uani 1 1 d . .
C17 C 0.83316(17) 0.99266(16) 0.4917(3) 0.0572(6) Uani 1 1 d . .
C18 C 0.08455(15) 0.81118(14) 0.1567(3) 0.0483(5) Uani 1 1 d . .
C19 C 0.72958(16) 1.03013(15) 0.4468(3) 0.0499(5) Uani 1 1 d . .
H1 H 0.4535(14) 0.9136(13) 0.258(2) 0.039(5) Uiso 1 1 d . .
H2 H 0.1690(15) 0.9937(14) -0.086(3) 0.051(5) Uiso 1 1 d . .
H3 H 0.1967(15) 0.7262(15) 0.293(3) 0.054(6) Uiso 1 1 d . .
H4 H 0.3405(16) 0.9366(13) 0.007(3) 0.048(5) Uiso 1 1 d . .
H5 H 0.5737(15) 0.9987(13) 0.360(2) 0.042(5) Uiso 1 1 d . .
H6 H 0.8902(17) 1.0340(17) 0.536(3) 0.065(6) Uiso 1 1 d . .
H7 H 0.0045(17) 0.9105(14) 0.010(3) 0.049(5) Uiso 1 1 d . .
H8 H 0.0166(18) 0.7754(16) 0.190(3) 0.064(6) Uiso 1 1 d . .
H9 H 0.9240(19) 0.8713(17) 0.506(3) 0.074(7) Uiso 1 1 d . .
H10 H 0.7190(17) 1.0967(17) 0.461(3) 0.062(6) Uiso 1 1 d . .
H11 H 0.7061(16) 0.6133(16) 0.363(3) 0.051(5) Uiso 1 1 d . .
H12 H 0.8569(18) 0.7126(15) 0.453(3) 0.058(6) Uiso 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
C3 N1 C5 120.65(14)
N1 C3 C6 122.10(16)
C7 C4 C8 117.28(15)
C7 C4 C6 123.50(15)
C8 C4 C6 119.20(15)
C10 C5 C12 119.28(15)
C10 C5 N1 123.20(15)
C12 C5 N1 117.49(15)
C9 C6 C3 119.70(14)
C9 C6 C4 119.31(14)
C3 C6 C4 120.99(15)
C19 C7 C4 121.45(17)
C16 C8 C11 121.78(16)
C16 C8 C4 119.61(18)
C11 C8 C4 118.58(15)
O1 C9 C6 122.64(14)
O1 C9 C13 117.32(16)
C6 C9 C13 120.03(16)
C14 C10 C5 119.95(17)
C13 C11 C8 122.08(16)
C18 C12 C5 120.23(18)
C11 C13 C9 120.71(18)
C15 C14 C10 120.21(18)
C14 C15 C18 120.14(17)
C17 C16 C8 121.46(18)
C16 C17 C19 119.29(18)
C12 C18 C15 120.15(18)
C7 C19 C17 120.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C3 1.294(2)
N1 C5 1.415(2)
O1 C9 1.331(2)
C3 C6 1.437(2)
C4 C7 1.412(3)
C4 C8 1.421(2)
C4 C6 1.442(2)
C5 C10 1.391(2)
C5 C12 1.396(2)
C6 C9 1.401(2)
C7 C19 1.371(2)
C8 C16 1.415(3)
C8 C11 1.421(3)
C9 C13 1.417(2)
C10 C14 1.388(2)
C11 C13 1.344(3)
C12 C18 1.380(3)
C14 C15 1.380(3)
C15 C18 1.381(3)
C16 C17 1.358(3)
C17 C19 1.400(3)
