#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:24:13 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250096 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038019.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_4038019
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_moiety         'C21 H13 N'
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 111.313(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1743(10)
_cell_length_b                   8.2226(6)
_cell_length_c                   13.5000(10)
_cell_measurement_reflns_used    6857
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.71
_cell_volume                     1362.40(18)
_computing_cell_refinement       'Saint+ ver. V8.38A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.38A (Bruker AXS)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_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            36929
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.095
_diffrn_reflns_theta_min         1.850
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.423
_exptl_crystal_size_mid          0.403
_exptl_crystal_size_min          0.174
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2998
_refine_ls_number_restraints     321
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0406
_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)+(0.0526P)²+0.6946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2356
_reflns_number_total             2998
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03421_si_001.cif
_cod_data_source_block           GoKo35_a
_cod_depositor_comments
'Adding full bibliography for 4038018--4038031.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038019
_shelx_shelxl_version_number     2018/3
_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   0.967
_shelx_estimated_absorpt_t_max   0.986
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 0.87762(10) 0.93362(16) 0.37473(10) 0.0237(3) Uani 1 1 d . . . . .
C1 C 0.52384(11) 0.61228(16) 0.33340(10) 0.0153(3) Uani 1 1 d . U . . .
H1 H 0.545805 0.568616 0.279171 0.018 Uiso 1 1 calc R U . . .
C2 C 0.59342(11) 0.71831(16) 0.40862(11) 0.0149(3) Uani 1 1 d . U . . .
C3 C 0.56320(11) 0.77739(16) 0.49103(11) 0.0156(3) Uani 1 1 d . U . . .
H3 H 0.612362 0.844524 0.544272 0.019 Uiso 1 1 calc R U . . .
C4 C 0.46202(11) 0.73948(16) 0.49648(10) 0.0141(3) Uani 1 1 d . U . . .
C5 C 0.42531(11) 0.81033(17) 0.57515(10) 0.0168(3) Uani 1 1 d . U . . .
H5 H 0.474307 0.874825 0.630269 0.020 Uiso 1 1 calc R U . . .
C8 C 0.13784(12) 0.66728(18) 0.48406(11) 0.0198(3) Uani 1 1 d . U . . .
H8 H 0.113199 0.719290 0.534025 0.024 Uiso 1 1 calc R U . . .
C7 C 0.24627(11) 0.68756(16) 0.49188(10) 0.0157(3) Uani 1 1 d . U . . .
C6 C 0.32274(12) 0.78712(17) 0.57231(11) 0.0174(3) Uani 1 1 d . U . . .
H6 H 0.300679 0.837604 0.624517 0.021 Uiso 1 1 calc R U . . .
C9 C 0.06605(12) 0.57190(18) 0.40400(12) 0.0208(3) Uani 1 1 d . U . . .
H9 H -0.007048 0.559151 0.399860 0.025 Uiso 1 1 calc R U . . .
C10 C 0.10034(11) 0.49549(17) 0.33036(11) 0.0192(3) Uani 1 1 d . U . . .
H10 H 0.050629 0.429625 0.276673 0.023 Uiso 1 1 calc R U . . .
C11 C 0.20755(11) 0.51387(16) 0.33381(11) 0.0159(3) Uani 1 1 d . U . . .
C12 C 0.24471(12) 0.44177(17) 0.25617(11) 0.0195(3) Uani 1 1 d . U . . .
H12 H 0.196363 0.374553 0.202368 0.023 Uiso 1 1 calc R U . . .
C13 C 0.34693(12) 0.46706(17) 0.25760(11) 0.0180(3) Uani 1 1 d . U . . .
H13 H 0.369038 0.416330 0.205495 0.022 Uiso 1 1 calc R U . . .
C14 C 0.42237(11) 0.56950(16) 0.33676(10) 0.0143(3) Uani 1 1 d . U . . .
C15 C 0.38934(11) 0.63662(15) 0.41765(10) 0.0130(3) Uani 1 1 d . U . . .
C16 C 0.28156(11) 0.61027(16) 0.41559(10) 0.0139(3) Uani 1 1 d . U . . .
C17 C 0.69476(11) 0.78112(16) 0.39762(11) 0.0166(3) Uani 1 1 d . U . . .
C18 C 0.69827(12) 0.81590(18) 0.29766(11) 0.0197(3) Uani 1 1 d . U . . .
H18 H 0.638773 0.787480 0.235006 0.024 Uiso 1 1 calc R U . . .
C19 C 0.78933(12) 0.89230(18) 0.29050(12) 0.0226(3) Uani 1 1 d . U . . .
H19 H 0.789109 0.916848 0.221659 0.027 Uiso 1 1 calc R U . . .
C20 C 0.87488(12) 0.89498(19) 0.47056(12) 0.0228(3) Uani 1 1 d . U . . .
H20 H 0.937043 0.919885 0.531697 0.027 Uiso 1 1 calc R U . . .
C21 C 0.78702(12) 0.82109(18) 0.48568(12) 0.0204(3) Uani 1 1 d . U . . .
H21 H 0.789596 0.797825 0.555486 0.024 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 -1.00 0.2100
1.00 0.00 1.00 0.2110
1.00 1.00 1.00 0.1320
0.00 1.00 0.00 0.1980
-1.00 1.00 -1.00 0.2020
1.00 -1.00 1.00 0.1880
1.00 -1.00 0.00 0.1850
1.00 -1.00 -1.00 0.2020
0.00 0.00 -1.00 0.1890
-1.00 0.00 1.00 0.0200
1.00 0.00 -1.00 0.0870
-1.00 0.00 0.00 0.1620
-1.00 -1.00 1.00 0.1210
1.00 1.00 0.00 0.1870
-1.00 -1.00 0.00 0.1690
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
C19 N1 C20 115.92(13) . . ?
C2 C1 C14 121.01(12) . . ?
C2 C1 H1 119.5 . . ?
C14 C1 H1 119.5 . . ?
C3 C2 C1 119.58(12) . . ?
C3 C2 C17 118.95(12) . . ?
C1 C2 C17 121.26(12) . . ?
C4 C3 C2 121.18(12) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C15 119.27(12) . . ?
C3 C4 C5 122.09(12) . . ?
C15 C4 C5 118.49(12) . . ?
C6 C5 C4 121.48(13) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C9 C8 C7 120.76(13) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C7 C16 118.91(13) . . ?
C8 C7 C6 122.61(13) . . ?
C16 C7 C6 118.46(12) . . ?
C5 C6 C7 121.37(13) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C10 C9 C8 120.47(13) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.96(13) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C16 118.95(13) . . ?
C10 C11 C12 122.47(13) . . ?
C16 C11 C12 118.56(12) . . ?
C13 C12 C11 121.78(13) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 121.00(13) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C1 C14 C15 119.27(12) . . ?
C1 C14 C13 122.25(12) . . ?
C15 C14 C13 118.38(12) . . ?
C4 C15 C14 119.57(12) . . ?
C4 C15 C16 119.95(12) . . ?
C14 C15 C16 120.34(12) . . ?
C11 C16 C7 119.93(12) . . ?
C11 C16 C15 119.82(12) . . ?
C7 C16 C15 120.16(12) . . ?
C21 C17 C18 116.76(13) . . ?
C21 C17 C2 122.12(12) . . ?
C18 C17 C2 120.89(12) . . ?
C19 C18 C17 119.53(13) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
N1 C19 C18 124.09(14) . . ?
N1 C19 H19 118.0 . . ?
C18 C19 H19 118.0 . . ?
N1 C20 C21 124.11(14) . . ?
N1 C20 H20 117.9 . . ?
C21 C20 H20 117.9 . . ?
C20 C21 C17 119.53(14) . . ?
C20 C21 H21 120.2 . . ?
C17 C21 H21 120.2 . . ?
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 C19 1.3416(19) . ?
N1 C20 1.345(2) . ?
C1 C2 1.3982(19) . ?
C1 C14 1.3989(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.3978(19) . ?
C2 C17 1.4884(18) . ?
C3 C4 1.3967(19) . ?
C3 H3 0.9500 . ?
C4 C15 1.4227(18) . ?
C4 C5 1.4403(18) . ?
C5 C6 1.351(2) . ?
C5 H5 0.9500 . ?
C8 C9 1.391(2) . ?
C8 C7 1.403(2) . ?
C8 H8 0.9500 . ?
C7 C16 1.4243(18) . ?
C7 C6 1.4384(19) . ?
C6 H6 0.9500 . ?
C9 C10 1.383(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.4043(19) . ?
C10 H10 0.9500 . ?
C11 C16 1.4197(18) . ?
C11 C12 1.436(2) . ?
C12 C13 1.356(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.4378(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.4253(18) . ?
C15 C16 1.4266(18) . ?
C17 C21 1.3958(19) . ?
C17 C18 1.3966(19) . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.387(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
