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#$Date: 2020-04-04 07:24:13 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250096 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038028.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_4038028
loop_
_publ_author_name
'Lu, Qing'
'Kole, Goutam Kumar'
'Friedrich, Alexandra'
'Müller-Buschbaum, Klaus'
'Liu, Zhiqiang'
'Yu, Xiaoqiang'
'Marder, Todd B.'
_publ_section_title
;
 Comparison Study of the Site-Effect on Regioisomeric Pyridyl-Pyrene
 Conjugates: Synthesis, Structures, and Photophysical Properties.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4256
_journal_page_last               4266
_journal_paper_doi               10.1021/acs.joc.9b03421
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C13 H8 N'
_chemical_formula_weight         178.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.918(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.530(3)
_cell_length_b                   10.289(2)
_cell_length_c                   13.803(3)
_cell_measurement_reflns_used    4457
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.22
_cell_measurement_theta_min      6.64
_cell_volume                     1719.5(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0954
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9522
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.893
_diffrn_reflns_theta_min         6.051
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  0.896
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.496
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.496
_refine_ls_R_factor_all          0.1348
_refine_ls_R_factor_gt           0.1154
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3096
_refine_ls_wR_factor_ref         0.3471
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1361
_reflns_number_total             1717
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03421_si_001.cif
_cod_data_source_block           Liuzq201914-sad
_cod_depositor_comments
'Adding full bibliography for 4038018--4038031.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4038028
_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   0.834
_shelx_estimated_absorpt_t_max   0.896
_exptl_absorpt_special_details
;
about 2 hours for data collection, 
with scale.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1499(2) 0.4442(2) 0.8053(2) 0.0567(8) Uani 1 1 d . . . . .
C12 C 0.1324(2) 0.3893(3) 0.7156(3) 0.0549(9) Uani 1 1 d . . . . .
C13 C 0.2013(2) 0.4043(3) 0.6523(3) 0.0520(8) Uani 1 1 d . . . . .
C9 C 0.2947(2) 0.4844(2) 0.6822(2) 0.0447(8) Uani 1 1 d . . . . .
C8 C 0.3685(2) 0.5100(2) 0.6152(2) 0.0459(8) Uani 1 1 d . . . . .
C7 C 0.3748(2) 0.6335(3) 0.5809(2) 0.0504(8) Uani 1 1 d . . . . .
C6 C 0.4404(2) 0.6648(2) 0.5127(2) 0.0495(8) Uani 1 1 d . . . . .
C1 C 0.5023(2) 0.5644(2) 0.4821(2) 0.0445(8) Uani 1 1 d . . . . .
C2 C 0.5687(2) 0.5939(2) 0.4144(2) 0.0463(8) Uani 1 1 d . . . . .
C11 C 0.2400(3) 0.5193(3) 0.8338(3) 0.0551(9) Uani 1 1 d . . . . .
C10 C 0.3130(2) 0.5430(3) 0.7750(2) 0.0499(8) Uani 1 1 d . . . . .
C3 C 0.5679(2) 0.7210(3) 0.3780(2) 0.0508(8) Uani 1 1 d . . . . .
C4 C 0.5059(2) 0.8186(3) 0.4078(3) 0.0535(9) Uani 1 1 d . . . . .
C5 C 0.4436(2) 0.7914(2) 0.4738(2) 0.0501(8) Uani 1 1 d . . . . .
H10 H 0.384(4) 0.607(4) 0.805(4) 0.077(12) Uiso 1 1 d . . . . .
H11 H 0.252(3) 0.561(3) 0.901(3) 0.056(9) Uiso 1 1 d . . . . .
H12 H 0.059(3) 0.327(3) 0.694(2) 0.049(8) Uiso 1 1 d . . . . .
H13 H 0.186(3) 0.364(3) 0.587(3) 0.055(9) Uiso 1 1 d . . . . .
H3 H 0.609(4) 0.734(4) 0.333(3) 0.068(10) Uiso 1 1 d . . . . .
H4 H 0.498(3) 0.923(3) 0.384(3) 0.058(9) Uiso 1 1 d . . . . .
H5 H 0.391(4) 0.850(5) 0.500(4) 0.091(15) Uiso 1 1 d . . . . .
H7 H 0.335(3) 0.709(3) 0.595(2) 0.042(7) 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 0.0181 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'
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
C12 N1 C11 116.3(3) . . ?
N1 C12 C13 124.1(3) . . ?
N1 C12 H12 115.3(17) . . ?
C13 C12 H12 120.6(17) . . ?
C12 C13 C9 119.3(3) . . ?
C12 C13 H13 122(2) . . ?
C9 C13 H13 118(2) . . ?
C10 C9 C13 117.1(3) . . ?
C10 C9 C8 121.2(2) . . ?
C13 C9 C8 121.7(3) . . ?
C7 C8 C2 120.3(3) . 5_666 ?
C7 C8 C9 118.7(2) . . ?
C2 C8 C9 120.9(2) 5_666 . ?
C8 C7 C6 122.0(3) . . ?
C8 C7 H7 126.7(18) . . ?
C6 C7 H7 111.2(18) . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 122.2(3) . . ?
C1 C6 C7 118.7(2) . . ?
C6 C1 C1 120.1(3) . 5_666 ?
C6 C1 C2 119.5(2) . . ?
C1 C1 C2 120.3(3) 5_666 . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 C8 122.9(3) . 5_666 ?
C1 C2 C8 118.5(2) . 5_666 ?
N1 C11 C10 124.1(3) . . ?
N1 C11 H11 116(2) . . ?
C10 C11 H11 120(2) . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 H10 122(2) . . ?
C11 C10 H10 118(2) . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 123(3) . . ?
C2 C3 H3 116(3) . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 111(2) . . ?
C3 C4 H4 128(2) . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 130(3) . . ?
C6 C5 H5 109(3) . . ?
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
N1 C12 1.328(4) . ?
N1 C11 1.341(4) . ?
C12 C13 1.386(4) . ?
C12 H12 1.10(3) . ?
C13 C9 1.403(4) . ?
C13 H13 0.97(4) . ?
C9 C10 1.381(4) . ?
C9 C8 1.489(4) . ?
C8 C7 1.365(4) . ?
C8 C2 1.448(4) 5_666 ?
C7 C6 1.436(4) . ?
C7 H7 0.97(3) . ?
C6 C5 1.413(4) . ?
C6 C1 1.419(4) . ?
C1 C1 1.421(5) 5_666 ?
C1 C2 1.436(4) . ?
C2 C3 1.400(4) . ?
C2 C8 1.448(4) 5_666 ?
C11 C10 1.391(4) . ?
C11 H11 0.99(4) . ?
C10 H10 1.10(5) . ?
C3 C4 1.394(4) . ?
C3 H3 0.92(4) . ?
C4 C5 1.374(4) . ?
C4 H4 1.12(4) . ?
C5 H5 1.03(5) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C12 C13 0.7(4) . . . . ?
N1 C12 C13 C9 -1.5(5) . . . . ?
C12 C13 C9 C10 0.7(4) . . . . ?
C12 C13 C9 C8 -176.7(2) . . . . ?
C10 C9 C8 C7 -62.8(4) . . . . ?
C13 C9 C8 C7 114.5(3) . . . . ?
C10 C9 C8 C2 118.2(3) . . . 5_666 ?
C13 C9 C8 C2 -64.5(4) . . . 5_666 ?
C2 C8 C7 C6 1.7(5) 5_666 . . . ?
C9 C8 C7 C6 -177.3(3) . . . . ?
C8 C7 C6 C5 177.4(3) . . . . ?
C8 C7 C6 C1 -1.4(5) . . . . ?
C5 C6 C1 C1 -178.1(3) . . . 5_666 ?
C7 C6 C1 C1 0.7(5) . . . 5_666 ?
C5 C6 C1 C2 1.5(4) . . . . ?
C7 C6 C1 C2 -179.7(3) . . . . ?
C6 C1 C2 C3 -1.9(4) . . . . ?
C1 C1 C2 C3 177.7(3) 5_666 . . . ?
C6 C1 C2 C8 179.7(3) . . . 5_666 ?
C1 C1 C2 C8 -0.7(5) 5_666 . . 5_666 ?
C12 N1 C11 C10 0.8(4) . . . . ?
C13 C9 C10 C11 0.6(4) . . . . ?
C8 C9 C10 C11 178.0(2) . . . . ?
N1 C11 C10 C9 -1.5(4) . . . . ?
C1 C2 C3 C4 1.3(5) . . . . ?
C8 C2 C3 C4 179.6(3) 5_666 . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C1 C6 C5 C4 -0.4(5) . . . . ?
C7 C6 C5 C4 -179.2(3) . . . . ?
