#------------------------------------------------------------------------------
#$Date: 2020-08-06 15:47:50 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/66/7126619.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_7126619
loop_
_publ_author_name
'Adil, Laxmi Raman'
'Iyer, Parameswar Krishnan'
_publ_section_title
;
 Effects of incorporating regioisomers and flexible rotors to direct
 aggregation induced emission to achieve stimuli-responsive luminogens,
 security inks and chemical warfare agent sensors.
;
_journal_issue                   55
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7633
_journal_page_last               7636
_journal_paper_doi               10.1039/d0cc02318c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C25 H17 N'
_chemical_formula_weight         331.39
_chemical_name_systematic
4-(2-((9H-fluoren-9-ylidene)methyl)phenyl)pyridine
_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
_audit_update_record
;
2019-07-17 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.549(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8722(15)
_cell_length_b                   6.0689(4)
_cell_length_c                   18.7149(19)
_cell_measurement_reflns_used    1982
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.7540
_cell_measurement_theta_min      3.5450
_cell_volume                     1794.4(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6493
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.048
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         3.266
_exptl_absorpt_coefficient_mu    0.071
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       blcok
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.185
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0832
_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          0.2526
_refine_ls_wR_factor_ref         0.3373
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2105
_reflns_number_total             3183
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02318c3.cif
_cod_data_source_block           exp_5475
_cod_depositor_comments
'Adding full bibliography for 7126617--7126620.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7126619
_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.
;
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 0.8344(2) 0.3426(5) 0.33392(19) 0.0691(10) Uani 1 1 d . . . . .
C24 C 0.72656(19) 0.6396(5) 0.37286(19) 0.0483(8) Uani 1 1 d . . . . .
C15 C 0.67132(19) 0.7958(5) 0.39555(19) 0.0468(8) Uani 1 1 d . . . . .
C2 C 0.3847(2) 0.3143(6) 0.1786(2) 0.0550(9) Uani 1 1 d . . . . .
C16 C 0.5851(2) 0.8231(5) 0.3516(2) 0.0497(9) Uani 1 1 d . . . . .
C8 C 0.4767(2) 0.5814(5) 0.2547(2) 0.0530(9) Uani 1 1 d . . . . .
C23 C 0.7005(2) 0.4274(5) 0.3462(2) 0.0528(9) Uani 1 1 d . . . . .
H23 H 0.6464 0.3791 0.3406 0.063 Uiso 1 1 calc R U . . .
C9 C 0.42321(19) 0.4915(5) 0.2972(2) 0.0537(9) Uani 1 1 d . . . . .
C7 C 0.44700(19) 0.4677(6) 0.1797(2) 0.0539(9) Uani 1 1 d . . . . .
C14 C 0.54656(19) 0.7089(5) 0.2774(2) 0.0533(9) Uani 1 1 d . . . . .
H14 H 0.5738 0.7273 0.2424 0.064 Uiso 1 1 calc R U . . .
C1 C 0.36972(19) 0.3300(6) 0.2509(2) 0.0561(10) Uani 1 1 d . . . . .
C10 C 0.3141(2) 0.2118(6) 0.2774(3) 0.0646(11) Uani 1 1 d . . . . .
H10 H 0.2779 0.1072 0.2464 0.078 Uiso 1 1 calc R U . . .
C25 C 0.8093(2) 0.6965(5) 0.3786(2) 0.0575(10) Uani 1 1 d . . . . .
H25 H 0.8299 0.8367 0.3950 0.069 Uiso 1 1 calc R U . . .
C22 C 0.7561(2) 0.2888(6) 0.3279(2) 0.0625(10) Uani 1 1 d . . . . .
H22 H 0.7372 0.1483 0.3102 0.075 Uiso 1 1 calc R U . . .
C20 C 0.7055(2) 0.9168(6) 0.4627(2) 0.0608(10) Uani 1 1 d . . . . .
H20 H 0.7624 0.8985 0.4921 0.073 Uiso 1 1 calc R U . . .
C13 C 0.4219(2) 0.5298(6) 0.3694(2) 0.0617(10) Uani 1 1 d . . . . .
H13 H 0.4572 0.6357 0.4006 0.074 Uiso 1 1 calc R U . . .
C17 C 0.5380(2) 0.9734(6) 0.3764(2) 0.0628(11) Uani 1 1 d . . . . .
H17 H 0.4815 0.9967 0.3469 0.075 Uiso 1 1 calc R U . . .
C19 C 0.6576(3) 1.0625(6) 0.4867(2) 0.0649(10) Uani 1 1 d . . . . .
H19 H 0.6821 1.1426 0.5315 0.078 Uiso 1 1 calc R U . . .
C12 C 0.3673(2) 0.4087(7) 0.3951(3) 0.0674(11) Uani 1 1 d . . . . .
H12 H 0.3667 0.4333 0.4440 0.081 Uiso 1 1 calc R U . . .
C18 C 0.5730(3) 1.0890(6) 0.4440(3) 0.0684(11) Uani 1 1 d . . . . .
H18 H 0.5397 1.1839 0.4605 0.082 Uiso 1 1 calc R U . . .
C6 C 0.4729(2) 0.4878(6) 0.1171(2) 0.0655(11) Uani 1 1 d . . . . .
H6 H 0.5136 0.5913 0.1173 0.079 Uiso 1 1 calc R U . . .
C3 C 0.3511(2) 0.1757(6) 0.1158(3) 0.0685(11) Uani 1 1 d . . . . .
H3 H 0.3111 0.0698 0.1155 0.082 Uiso 1 1 calc R U . . .
C26 C 0.8596(2) 0.5471(6) 0.3602(3) 0.0711(12) Uani 1 1 d . . . . .
H26 H 0.9145 0.5891 0.3661 0.085 Uiso 1 1 calc R U . . .
C11 C 0.3135(2) 0.2512(7) 0.3489(3) 0.0702(11) Uani 1 1 d . . . . .
H11 H 0.2770 0.1726 0.3668 0.084 Uiso 1 1 calc R U . . .
C5 C 0.4372(2) 0.3516(7) 0.0545(2) 0.0734(12) Uani 1 1 d . . . . .
H5 H 0.4536 0.3645 0.0121 0.088 Uiso 1 1 calc R U . . .
C4 C 0.3771(3) 0.1962(7) 0.0549(3) 0.0768(12) Uani 1 1 d . . . . .
H4 H 0.3541 0.1043 0.0129 0.092 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
C22 N1 C26 115.7(3) . . ?
C23 C24 C25 115.7(3) . . ?
C23 C24 C15 122.6(3) . . ?
C25 C24 C15 121.7(3) . . ?
C20 C15 C16 118.7(3) . . ?
C20 C15 C24 119.3(3) . . ?
C16 C15 C24 121.9(3) . . ?
C3 C2 C7 119.7(4) . . ?
C3 C2 C1 131.8(3) . . ?
C7 C2 C1 108.4(3) . . ?
C17 C16 C15 118.4(3) . . ?
C17 C16 C14 120.3(3) . . ?
C15 C16 C14 121.1(3) . . ?
C14 C8 C7 122.2(3) . . ?
C14 C8 C9 131.6(3) . . ?
C7 C8 C9 105.4(3) . . ?
C22 C23 C24 119.5(3) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C13 C9 C1 119.6(3) . . ?
C13 C9 C8 132.7(3) . . ?
C1 C9 C8 107.6(3) . . ?
C6 C7 C2 120.2(3) . . ?
C6 C7 C8 130.8(3) . . ?
C2 C7 C8 109.0(3) . . ?
C8 C14 C16 127.7(4) . . ?
C8 C14 H14 116.1 . . ?
C16 C14 H14 116.1 . . ?
C10 C1 C9 120.2(4) . . ?
C10 C1 C2 130.3(3) . . ?
C9 C1 C2 109.4(3) . . ?
C11 C10 C1 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C1 C10 H10 120.2 . . ?
C26 C25 C24 120.4(3) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
N1 C22 C23 124.6(3) . . ?
N1 C22 H22 117.7 . . ?
C23 C22 H22 117.7 . . ?
C19 C20 C15 121.9(3) . . ?
C19 C20 H20 119.0 . . ?
C15 C20 H20 119.0 . . ?
C9 C13 C12 119.4(4) . . ?
C9 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C18 C17 C16 121.7(3) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C20 C19 C18 119.5(4) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C19 C18 C17 119.6(4) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C5 C6 C7 119.2(4) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
N1 C26 C25 124.0(3) . . ?
N1 C26 H26 118.0 . . ?
C25 C26 H26 118.0 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C3 C4 C5 121.2(4) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
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 C22 1.327(5) . ?
N1 C26 1.347(5) . ?
C24 C23 1.395(5) . ?
C24 C25 1.405(5) . ?
C24 C15 1.492(5) . ?
C15 C20 1.394(5) . ?
C15 C16 1.407(4) . ?
C2 C3 1.394(5) . ?
C2 C7 1.399(5) . ?
C2 C1 1.464(5) . ?
C16 C17 1.393(5) . ?
C16 C14 1.482(5) . ?
C8 C14 1.347(4) . ?
C8 C7 1.485(5) . ?
C8 C9 1.500(5) . ?
C23 C22 1.389(5) . ?
C23 H23 0.9300 . ?
C9 C13 1.380(5) . ?
C9 C1 1.405(5) . ?
C7 C6 1.391(5) . ?
C14 H14 0.9300 . ?
C1 C10 1.402(5) . ?
C10 C11 1.363(6) . ?
C10 H10 0.9300 . ?
C25 C26 1.366(5) . ?
C25 H25 0.9300 . ?
C22 H22 0.9300 . ?
C20 C19 1.375(5) . ?
C20 H20 0.9300 . ?
C13 C12 1.390(5) . ?
C13 H13 0.9300 . ?
C17 C18 1.384(6) . ?
C17 H17 0.9300 . ?
C19 C18 1.379(5) . ?
C19 H19 0.9300 . ?
C12 C11 1.391(6) . ?
C12 H12 0.9300 . ?
C18 H18 0.9300 . ?
C6 C5 1.388(5) . ?
C6 H6 0.9300 . ?
C3 C4 1.364(6) . ?
C3 H3 0.9300 . ?
C26 H26 0.9300 . ?
C11 H11 0.9300 . ?
C5 C4 1.387(6) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
