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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/4/03/80/4038021.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_4038021
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 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 96.486(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   4.623(5)
_cell_length_b                   22.358(5)
_cell_length_c                   13.545(5)
_cell_measurement_reflns_used    2782
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      2.37
_cell_volume                     1391.1(16)
_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      297(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15603
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         28.016
_diffrn_reflns_theta_min         1.766
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0532
_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)+(0.0844P)²+0.2628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1866
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1704
_reflns_number_total             3269
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03421_si_001.cif
_cod_data_source_block           slq_3_3_1_0m
_cod_depositor_comments
'Adding full bibliography for 4038018--4038031.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038021
_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   0.990
_shelx_estimated_absorpt_t_max   0.999
_exptl_absorpt_special_details
;
about 5 hours for data collection, 
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C12 C 0.4607(4) 0.12283(8) 0.79487(13) 0.0416(4) Uani 1 1 d . . . . .
C15 C 0.6719(4) 0.16832(8) 0.82058(14) 0.0446(5) Uani 1 1 d . . . . .
C13 C 0.3868(4) 0.08174(8) 0.86820(13) 0.0446(5) Uani 1 1 d . . . . .
C2 C 0.0502(4) 0.03102(8) 0.74402(13) 0.0449(5) Uani 1 1 d . . . . .
C14 C 0.7440(4) 0.20931(8) 0.74675(15) 0.0521(5) Uani 1 1 d . . . . .
C3 C 0.1223(4) 0.07209(9) 0.67292(14) 0.0493(5) Uani 1 1 d . . . . .
H3 H 0.0341 0.0687 0.6080 0.059 Uiso 1 1 calc R U . . .
C16 C 0.8109(4) 0.17263(8) 0.91939(15) 0.0496(5) Uani 1 1 d . . . . .
C21 C -0.1608(4) -0.01819(9) 0.71617(14) 0.0493(5) Uani 1 1 d . U . . .
C1 C 0.1822(4) 0.03712(8) 0.84111(13) 0.0468(5) Uani 1 1 d . . . . .
H1 H 0.1324 0.0106 0.8894 0.056 Uiso 1 1 calc R U . . .
C11 C 0.3222(4) 0.11783(8) 0.69657(13) 0.0452(5) Uani 1 1 d . . . . .
C22 C -0.2238(5) -0.05846(9) 0.78501(16) 0.0580(6) Uani 1 1 d . U . . .
H22 H -0.1357 -0.0559 0.8501 0.070 Uiso 1 1 calc R U . . .
C5 C 0.5981(5) 0.20360(10) 0.64809(16) 0.0605(6) Uani 1 1 d . . . . .
H5 H 0.6426 0.2303 0.5993 0.073 Uiso 1 1 calc R U . . .
C6 C 0.9560(5) 0.25288(9) 0.77392(18) 0.0622(6) Uani 1 1 d . . . . .
H6 H 1.0060 0.2799 0.7265 0.075 Uiso 1 1 calc R U . . .
C4 C 0.3989(5) 0.16082(10) 0.62426(15) 0.0582(6) Uani 1 1 d . . . . .
H4 H 0.3079 0.1588 0.5595 0.070 Uiso 1 1 calc R U . . .
C8 C 1.0201(5) 0.21725(10) 0.94183(17) 0.0615(6) Uani 1 1 d . . . . .
H8 H 1.1123 0.2206 1.0063 0.074 Uiso 1 1 calc R U . . .
C9 C 0.7298(5) 0.13075(10) 0.99137(15) 0.0581(6) Uani 1 1 d . . . . .
H9 H 0.8188 0.1331 1.0564 0.070 Uiso 1 1 calc R U . . .
N1 N -0.2836(5) -0.02144(10) 0.61994(16) 0.0853(7) Uani 1 1 d . U . . .
C10 C 0.5290(5) 0.08819(9) 0.96771(14) 0.0544(5) Uani 1 1 d . . . . .
H10 H 0.4806 0.0622 1.0169 0.065 Uiso 1 1 calc R U . . .
C7 C 1.0913(5) 0.25629(10) 0.8695(2) 0.0671(6) Uani 1 1 d . . . . .
H7 H 1.2328 0.2853 0.8856 0.081 Uiso 1 1 calc R U . . .
C24 C -0.5503(6) -0.10753(12) 0.6636(3) 0.0852(9) Uani 1 1 d . . . . .
H24 H -0.6850 -0.1376 0.6459 0.102 Uiso 1 1 calc R U . . .
C25 C -0.4796(7) -0.06688(13) 0.5961(2) 0.0907(9) Uani 1 1 d . . . . .
H25 H -0.5672 -0.0698 0.5310 0.109 Uiso 1 1 calc R U . . .
C23 C -0.4184(6) -0.10286(12) 0.7576(2) 0.0822(8) Uani 1 1 d . U . . .
H23 H -0.4616 -0.1307 0.8048 0.099 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
C11 C12 C15 120.72(16) . . ?
C11 C12 C13 119.15(17) . . ?
C15 C12 C13 120.13(17) . . ?
C12 C15 C14 119.74(18) . . ?
C12 C15 C16 120.20(17) . . ?
C14 C15 C16 120.06(19) . . ?
C1 C13 C12 119.17(17) . . ?
C1 C13 C10 122.86(17) . . ?
C12 C13 C10 117.97(18) . . ?
C1 C2 C3 118.24(18) . . ?
C1 C2 C21 121.05(17) . . ?
C3 C2 C21 120.71(17) . . ?
C6 C14 C15 118.4(2) . . ?
C6 C14 C5 123.26(19) . . ?
C15 C14 C5 118.35(19) . . ?
C11 C3 C2 121.88(18) . . ?
C11 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C8 C16 C15 118.77(19) . . ?
C8 C16 C9 123.10(19) . . ?
C15 C16 C9 118.12(18) . . ?
N1 C21 C22 121.7(2) . . ?
N1 C21 C2 118.11(18) . . ?
C22 C21 C2 120.20(18) . . ?
C13 C1 C2 122.01(17) . . ?
C13 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C11 C12 119.53(17) . . ?
C3 C11 C4 122.72(18) . . ?
C12 C11 C4 117.75(18) . . ?
C21 C22 C23 119.0(2) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C4 C5 C14 121.72(19) . . ?
C4 C5 H5 119.1 . . ?
C14 C5 H5 119.1 . . ?
C7 C6 C14 121.1(2) . . ?
C7 C6 H6 119.5 . . ?
C14 C6 H6 119.5 . . ?
C5 C4 C11 121.71(19) . . ?
C5 C4 H4 119.1 . . ?
C11 C4 H4 119.1 . . ?
C7 C8 C16 120.8(2) . . ?
C7 C8 H8 119.6 . . ?
C16 C8 H8 119.6 . . ?
C10 C9 C16 121.88(19) . . ?
C10 C9 H9 119.1 . . ?
C16 C9 H9 119.1 . . ?
C21 N1 C25 117.1(2) . . ?
C9 C10 C13 121.68(19) . . ?
C9 C10 H10 119.2 . . ?
C13 C10 H10 119.2 . . ?
C6 C7 C8 120.9(2) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C23 C24 C25 117.8(3) . . ?
C23 C24 H24 121.1 . . ?
C25 C24 H24 121.1 . . ?
C24 C25 N1 122.6(3) . . ?
C24 C25 H25 118.7 . . ?
N1 C25 H25 118.7 . . ?
C24 C23 C22 121.8(2) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
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
C12 C11 1.415(2) . ?
C12 C15 1.425(3) . ?
C12 C13 1.423(2) . ?
C15 C14 1.424(3) . ?
C15 C16 1.421(3) . ?
C13 C1 1.395(3) . ?
C13 C10 1.439(3) . ?
C2 C1 1.392(3) . ?
C2 C3 1.398(3) . ?
C2 C21 1.490(3) . ?
C14 C6 1.401(3) . ?
C14 C5 1.433(3) . ?
C3 C11 1.391(3) . ?
C3 H3 0.9300 . ?
C16 C8 1.399(3) . ?
C16 C9 1.432(3) . ?
C21 N1 1.363(3) . ?
C21 C22 1.351(3) . ?
C1 H1 0.9300 . ?
C11 C4 1.445(3) . ?
C22 C23 1.363(3) . ?
C22 H22 0.9300 . ?
C5 C4 1.341(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(3) . ?
C6 H6 0.9300 . ?
C4 H4 0.9300 . ?
C8 C7 1.379(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.343(3) . ?
C9 H9 0.9300 . ?
N1 C25 1.376(3) . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?
C24 C23 1.352(4) . ?
C24 C25 1.355(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C23 H23 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
C11 C12 C15 C14 0.2(3) . . . . ?
C13 C12 C15 C14 -179.88(16) . . . . ?
C11 C12 C15 C16 -179.56(16) . . . . ?
C13 C12 C15 C16 0.4(3) . . . . ?
C11 C12 C13 C1 0.7(2) . . . . ?
C15 C12 C13 C1 -179.21(16) . . . . ?
C11 C12 C13 C10 -179.46(16) . . . . ?
C15 C12 C13 C10 0.6(2) . . . . ?
C12 C15 C14 C6 -178.93(16) . . . . ?
C16 C15 C14 C6 0.8(3) . . . . ?
C12 C15 C14 C5 0.5(3) . . . . ?
C16 C15 C14 C5 -179.76(17) . . . . ?
C1 C2 C3 C11 0.7(3) . . . . ?
C21 C2 C3 C11 -178.91(16) . . . . ?
C12 C15 C16 C8 179.10(16) . . . . ?
C14 C15 C16 C8 -0.6(3) . . . . ?
C12 C15 C16 C9 -0.8(3) . . . . ?
C14 C15 C16 C9 179.51(17) . . . . ?
C1 C2 C21 N1 179.62(18) . . . . ?
C3 C2 C21 N1 -0.8(3) . . . . ?
C1 C2 C21 C22 -1.1(3) . . . . ?
C3 C2 C21 C22 178.46(18) . . . . ?
C12 C13 C1 C2 0.8(3) . . . . ?
C10 C13 C1 C2 -178.97(17) . . . . ?
C3 C2 C1 C13 -1.5(3) . . . . ?
C21 C2 C1 C13 178.04(16) . . . . ?
C2 C3 C11 C12 0.9(3) . . . . ?
C2 C3 C11 C4 -179.79(18) . . . . ?
C15 C12 C11 C3 178.38(16) . . . . ?
C13 C12 C11 C3 -1.6(2) . . . . ?
C15 C12 C11 C4 -1.0(2) . . . . ?
C13 C12 C11 C4 179.08(17) . . . . ?
N1 C21 C22 C23 -1.0(3) . . . . ?
C2 C21 C22 C23 179.74(19) . . . . ?
C6 C14 C5 C4 179.1(2) . . . . ?
C15 C14 C5 C4 -0.4(3) . . . . ?
C15 C14 C6 C7 -0.2(3) . . . . ?
C5 C14 C6 C7 -179.6(2) . . . . ?
C14 C5 C4 C11 -0.5(3) . . . . ?
C3 C11 C4 C5 -178.19(19) . . . . ?
C12 C11 C4 C5 1.2(3) . . . . ?
C15 C16 C8 C7 -0.2(3) . . . . ?
C9 C16 C8 C7 179.66(19) . . . . ?
C8 C16 C9 C10 -179.73(19) . . . . ?
C15 C16 C9 C10 0.1(3) . . . . ?
C22 C21 N1 C25 1.3(3) . . . . ?
C2 C21 N1 C25 -179.4(2) . . . . ?
C16 C9 C10 C13 0.9(3) . . . . ?
C1 C13 C10 C9 178.55(18) . . . . ?
C12 C13 C10 C9 -1.3(3) . . . . ?
C14 C6 C7 C8 -0.7(3) . . . . ?
C16 C8 C7 C6 0.8(3) . . . . ?
C23 C24 C25 N1 -0.7(4) . . . . ?
C21 N1 C25 C24 -0.4(4) . . . . ?
C25 C24 C23 C22 1.0(4) . . . . ?
C21 C22 C23 C24 -0.2(4) . . . . ?
