#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:24:13 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250096 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038020.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_4038020
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            'C21 H13 N'
_chemical_formula_weight         279.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 110.722(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.194(3)
_cell_length_b                   8.3516(17)
_cell_length_c                   13.506(3)
_cell_measurement_reflns_used    2516
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.28
_cell_measurement_theta_min      2.68
_cell_volume                     1392.0(5)
_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      296(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.1147
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18936
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.583
_diffrn_reflns_theta_min         1.855
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      1.338
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0520
_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)+0.0483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1647
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1833
_reflns_number_total             3167
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03421_si_001.cif
_cod_data_source_block           liuzq201212
_cod_depositor_comments
'Adding full bibliography for 4038018--4038031.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038020
_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   0.941
_shelx_estimated_absorpt_t_max   0.992
_exptl_absorpt_special_details
;
about 6 hours for data collection, 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 -0.37875(14) 0.5729(2) 0.12225(17) 0.0772(6) Uani 1 1 d . . . . .
C23 C -0.29159(19) 0.6130(3) 0.2056(2) 0.0759(7) Uani 1 1 d . . . . .
H23 H -0.2925 0.5901 0.2727 0.091 Uiso 1 1 calc R U . . .
C22 C -0.20078(16) 0.6856(2) 0.19905(16) 0.0626(6) Uani 1 1 d . . . . .
H22 H -0.1433 0.7120 0.2603 0.075 Uiso 1 1 calc R U . . .
C21 C -0.19536(14) 0.71903(19) 0.10093(15) 0.0497(5) Uani 1 1 d . . . . .
C2 C -0.09404(14) 0.77961(19) 0.09062(14) 0.0446(4) Uani 1 1 d . . . . .
C3 C -0.06159(14) 0.72289(19) 0.01032(14) 0.0458(4) Uani 1 1 d . . . . .
H3 H -0.1087 0.6585 -0.0421 0.055 Uiso 1 1 calc R U . . .
C11 C 0.03918(13) 0.75927(18) 0.00567(12) 0.0403(4) Uani 1 1 d . . . . .
C12 C 0.10985(13) 0.86214(17) 0.08399(12) 0.0384(4) Uani 1 1 d . . . . .
C15 C 0.21679(13) 0.88953(18) 0.08637(12) 0.0402(4) Uani 1 1 d . . . . .
C14 C 0.25340(14) 0.8151(2) 0.01173(13) 0.0467(5) Uani 1 1 d . . . . .
C6 C 0.36100(16) 0.8368(2) 0.02011(17) 0.0603(5) Uani 1 1 d . . . . .
H6 H 0.3864 0.7872 -0.0283 0.072 Uiso 1 1 calc R U . . .
C7 C 0.43004(16) 0.9306(2) 0.09907(18) 0.0660(6) Uani 1 1 d . . . . .
H7 H 0.5014 0.9438 0.1033 0.079 Uiso 1 1 calc R U . . .
C13 C 0.07510(14) 0.92721(18) 0.16260(13) 0.0431(4) Uani 1 1 d . . . . .
C10 C 0.14879(16) 1.0302(2) 0.24107(15) 0.0559(5) Uani 1 1 d . . . . .
H10 H 0.1259 1.0797 0.2912 0.067 Uiso 1 1 calc R U . . .
C9 C 0.24976(16) 1.0558(2) 0.24295(15) 0.0586(5) Uani 1 1 d . . . . .
H9 H 0.2957 1.1213 0.2954 0.070 Uiso 1 1 calc R U . . .
C16 C 0.28869(14) 0.9861(2) 0.16755(14) 0.0488(5) Uani 1 1 d . . . . .
C5 C 0.17903(16) 0.7156(2) -0.06800(14) 0.0531(5) Uani 1 1 d . . . . .
H5 H 0.2018 0.6670 -0.1185 0.064 Uiso 1 1 calc R U . . .
C4 C 0.07769(15) 0.6914(2) -0.07113(13) 0.0502(5) Uani 1 1 d . . . . .
H4 H 0.0311 0.6286 -0.1249 0.060 Uiso 1 1 calc R U . . .
C8 C 0.39513(16) 1.0047(2) 0.17140(16) 0.0599(5) Uani 1 1 d . . . . .
H8 H 0.4429 1.0682 0.2238 0.072 Uiso 1 1 calc R U . . .
C1 C -0.02597(14) 0.88511(19) 0.16489(14) 0.0481(5) Uani 1 1 d . . . . .
H1 H -0.0488 0.9281 0.2170 0.058 Uiso 1 1 calc R U . . .
C25 C -0.28610(15) 0.6801(2) 0.01372(17) 0.0626(6) Uani 1 1 d . . . . .
H25 H -0.2873 0.7014 -0.0543 0.075 Uiso 1 1 calc R U . . .
C24 C -0.37407(16) 0.6100(2) 0.0281(2) 0.0726(6) Uani 1 1 d . . . . .
H24 H -0.4342 0.5869 -0.0317 0.087 Uiso 1 1 calc R U . . .
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'
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
C24 N1 C23 115.45(18) . . ?
N1 C23 C22 124.5(2) . . ?
N1 C23 H23 117.8 . . ?
C22 C23 H23 117.8 . . ?
C23 C22 C21 119.6(2) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C21 C25 116.41(17) . . ?
C22 C21 C2 120.95(17) . . ?
C25 C21 C2 122.42(17) . . ?
C3 C2 C1 118.71(16) . . ?
C3 C2 C21 119.78(16) . . ?
C1 C2 C21 121.35(16) . . ?
C2 C3 C11 121.89(16) . . ?
C2 C3 H3 119.1 . . ?
C11 C3 H3 119.1 . . ?
C3 C11 C4 122.73(16) . . ?
C3 C11 C12 119.00(15) . . ?
C4 C11 C12 118.19(15) . . ?
C13 C12 C15 120.54(15) . . ?
C13 C12 C11 119.42(15) . . ?
C15 C12 C11 119.91(15) . . ?
C14 C15 C12 120.22(15) . . ?
C14 C15 C16 119.94(16) . . ?
C12 C15 C16 119.76(16) . . ?
C6 C14 C15 118.81(17) . . ?
C6 C14 C5 122.75(17) . . ?
C15 C14 C5 118.41(16) . . ?
C7 C6 C14 120.80(19) . . ?
C7 C6 H6 119.6 . . ?
C14 C6 H6 119.6 . . ?
C8 C7 C6 120.91(19) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C1 C13 C12 119.39(15) . . ?
C1 C13 C10 122.50(17) . . ?
C12 C13 C10 118.05(16) . . ?
C9 C10 C13 121.07(17) . . ?
C9 C10 H10 119.5 . . ?
C13 C10 H10 119.5 . . ?
C10 C9 C16 122.08(17) . . ?
C10 C9 H9 119.0 . . ?
C16 C9 H9 119.0 . . ?
C8 C16 C9 122.91(17) . . ?
C8 C16 C15 118.71(17) . . ?
C9 C16 C15 118.36(16) . . ?
C4 C5 C14 121.39(17) . . ?
C4 C5 H5 119.3 . . ?
C14 C5 H5 119.3 . . ?
C5 C4 C11 121.79(16) . . ?
C5 C4 H4 119.1 . . ?
C11 C4 H4 119.1 . . ?
C7 C8 C16 120.83(18) . . ?
C7 C8 H8 119.6 . . ?
C16 C8 H8 119.6 . . ?
C13 C1 C2 121.45(16) . . ?
C13 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C24 C25 C21 119.8(2) . . ?
C24 C25 H25 120.1 . . ?
C21 C25 H25 120.1 . . ?
N1 C24 C25 124.2(2) . . ?
N1 C24 H24 117.9 . . ?
C25 C24 H24 117.9 . . ?
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 C24 1.331(3) . ?
N1 C23 1.336(3) . ?
C23 C22 1.373(3) . ?
C23 H23 0.9300 . ?
C22 C21 1.381(2) . ?
C22 H22 0.9300 . ?
C21 C25 1.389(3) . ?
C21 C2 1.481(2) . ?
C2 C3 1.383(2) . ?
C2 C1 1.397(2) . ?
C3 C11 1.387(2) . ?
C3 H3 0.9300 . ?
C11 C4 1.424(2) . ?
C11 C12 1.424(2) . ?
C12 C13 1.406(2) . ?
C12 C15 1.418(2) . ?
C15 C14 1.407(2) . ?
C15 C16 1.420(2) . ?
C14 C6 1.396(2) . ?
C14 C5 1.437(2) . ?
C6 C7 1.376(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.367(3) . ?
C7 H7 0.9300 . ?
C13 C1 1.390(2) . ?
C13 C10 1.442(2) . ?
C10 C9 1.340(2) . ?
C10 H10 0.9300 . ?
C9 C16 1.418(2) . ?
C9 H9 0.9300 . ?
C16 C8 1.395(3) . ?
C5 C4 1.338(2) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C8 H8 0.9300 . ?
C1 H1 0.9300 . ?
C25 C24 1.374(3) . ?
C25 H25 0.9300 . ?
C24 H24 0.9300 . ?
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
C24 N1 C23 C22 -0.8(3) . . . . ?
N1 C23 C22 C21 -1.1(3) . . . . ?
C23 C22 C21 C25 1.9(3) . . . . ?
C23 C22 C21 C2 -172.79(17) . . . . ?
C22 C21 C2 C3 139.19(18) . . . . ?
C25 C21 C2 C3 -35.2(3) . . . . ?
C22 C21 C2 C1 -36.3(2) . . . . ?
C25 C21 C2 C1 149.32(17) . . . . ?
C1 C2 C3 C11 4.4(3) . . . . ?
C21 C2 C3 C11 -171.23(15) . . . . ?
C2 C3 C11 C4 174.60(15) . . . . ?
C2 C3 C11 C12 -2.0(3) . . . . ?
C3 C11 C12 C13 -1.4(2) . . . . ?
C4 C11 C12 C13 -178.21(14) . . . . ?
C3 C11 C12 C15 174.39(14) . . . . ?
C4 C11 C12 C15 -2.4(2) . . . . ?
C13 C12 C15 C14 175.63(13) . . . . ?
C11 C12 C15 C14 -0.1(2) . . . . ?
C13 C12 C15 C16 -1.3(2) . . . . ?
C11 C12 C15 C16 -177.04(13) . . . . ?
C12 C15 C14 C6 -176.17(15) . . . . ?
C16 C15 C14 C6 0.7(2) . . . . ?
C12 C15 C14 C5 1.8(2) . . . . ?
C16 C15 C14 C5 178.74(15) . . . . ?
C15 C14 C6 C7 -0.7(3) . . . . ?
C5 C14 C6 C7 -178.65(16) . . . . ?
C14 C6 C7 C8 0.1(3) . . . . ?
C15 C12 C13 C1 -173.34(14) . . . . ?
C11 C12 C13 C1 2.4(2) . . . . ?
C15 C12 C13 C10 3.9(2) . . . . ?
C11 C12 C13 C10 179.67(14) . . . . ?
C1 C13 C10 C9 173.24(17) . . . . ?
C12 C13 C10 C9 -3.9(3) . . . . ?
C13 C10 C9 C16 1.2(3) . . . . ?
C10 C9 C16 C8 -176.64(17) . . . . ?
C10 C9 C16 C15 1.5(3) . . . . ?
C14 C15 C16 C8 -0.1(2) . . . . ?
C12 C15 C16 C8 176.77(15) . . . . ?
C14 C15 C16 C9 -178.39(15) . . . . ?
C12 C15 C16 C9 -1.5(2) . . . . ?
C6 C14 C5 C4 176.95(17) . . . . ?
C15 C14 C5 C4 -1.0(3) . . . . ?
C14 C5 C4 C11 -1.7(3) . . . . ?
C3 C11 C4 C5 -173.32(16) . . . . ?
C12 C11 C4 C5 3.3(3) . . . . ?
C6 C7 C8 C16 0.5(3) . . . . ?
C9 C16 C8 C7 177.69(17) . . . . ?
C15 C16 C8 C7 -0.5(3) . . . . ?
C12 C13 C1 C2 -0.1(2) . . . . ?
C10 C13 C1 C2 -177.20(15) . . . . ?
C3 C2 C1 C13 -3.3(2) . . . . ?
C21 C2 C1 C13 172.24(15) . . . . ?
C22 C21 C25 C24 -0.9(3) . . . . ?
C2 C21 C25 C24 173.72(17) . . . . ?
C23 N1 C24 C25 1.9(3) . . . . ?
C21 C25 C24 N1 -1.1(3) . . . . ?
