#------------------------------------------------------------------------------
#$Date: 2020-08-06 15:47:50 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/66/7126620.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_7126620
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_moiety         'C25 H17 N'
_chemical_formula_sum            'C25 H17 N'
_chemical_formula_weight         331.39
_chemical_name_common
4-(2-((9H-fluoren-9-ylidene)methyl)phenyl)pyridine
_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-2018/3
_audit_update_record
;
2019-07-06 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.396(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8262(9)
_cell_length_b                   6.0687(3)
_cell_length_c                   18.6754(10)
_cell_measurement_reflns_used    1524
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.51
_cell_measurement_theta_min      3.59
_cell_volume                     1787.45(18)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.869
_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  0.0269
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7893
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.948
_diffrn_reflns_theta_min         2.327
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.981
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0552
_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)+(0.0472P)²+0.0665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1382
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2500
_reflns_number_total             4110
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02318c3.cif
_cod_data_source_block           1PON-2
_cod_depositor_comments
'Adding full bibliography for 7126617--7126620.cif.'
_cod_original_cell_volume        1787.45(17)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7126620
_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.
;
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
N21 N 0.16489(11) 0.6575(3) 0.66553(10) 0.0621(5) Uani 1 1 d . . . . .
C24 C 0.27311(10) 0.3608(3) 0.62746(10) 0.0406(4) Uani 1 1 d . . . . .
C15 C 0.32849(10) 0.2057(3) 0.60475(10) 0.0406(4) Uani 1 1 d . . . . .
C16 C 0.41495(11) 0.1779(3) 0.64842(11) 0.0427(4) Uani 1 1 d . . . . .
C14 C 0.45384(10) 0.2918(3) 0.72231(10) 0.0451(4) Uani 1 1 d . . . . .
H14 H 0.426554 0.272306 0.757429 0.054 Uiso 1 1 calc R U . . .
C1 C 0.63036(10) 0.6708(3) 0.74928(11) 0.0455(5) Uani 1 1 d . . . . .
C9 C 0.57644(10) 0.5090(3) 0.70331(11) 0.0444(5) Uani 1 1 d . . . . .
C8 C 0.52319(11) 0.4195(3) 0.74559(10) 0.0437(4) Uani 1 1 d . . . . .
C2 C 0.61516(11) 0.6871(3) 0.82169(11) 0.0472(5) Uani 1 1 d . . . . .
C7 C 0.55297(11) 0.5325(3) 0.82061(10) 0.0459(5) Uani 1 1 d . . . . .
C23 C 0.29916(12) 0.5725(3) 0.65406(11) 0.0474(5) Uani 1 1 d . . . . .
H23 H 0.353490 0.620534 0.659663 0.057 Uiso 1 1 calc R U . . .
C20 C 0.29401(12) 0.0841(3) 0.53764(11) 0.0515(5) Uani 1 1 d . . . . .
H20 H 0.237018 0.101666 0.508326 0.062 Uiso 1 1 calc R U . . .
C25 C 0.19104(11) 0.3045(3) 0.62091(11) 0.0511(5) Uani 1 1 d . . . . .
H25 H 0.170109 0.165250 0.603415 0.061 Uiso 1 1 calc R U . . .
C10 C 0.68533(12) 0.7895(3) 0.72369(12) 0.0559(5) Uani 1 1 d . . . . .
H10 H 0.721217 0.894681 0.754760 0.067 Uiso 1 1 calc R U . . .
C13 C 0.57788(12) 0.4712(3) 0.63054(11) 0.0523(5) Uani 1 1 d . . . . .
H13 H 0.542476 0.365729 0.599160 0.063 Uiso 1 1 calc R U . . .
C17 C 0.46207(12) 0.0272(3) 0.62313(12) 0.0547(5) Uani 1 1 d . . . . .
H17 H 0.518849 0.004966 0.652292 0.066 Uiso 1 1 calc R U . . .
C12 C 0.63280(13) 0.5927(3) 0.60501(13) 0.0599(6) Uani 1 1 d . . . . .
H12 H 0.633718 0.568314 0.556138 0.072 Uiso 1 1 calc R U . . .
C18 C 0.42688(14) -0.0895(3) 0.55623(13) 0.0607(6) Uani 1 1 d . . . . .
H18 H 0.459919 -0.186365 0.539933 0.073 Uiso 1 1 calc R U . . .
C6 C 0.52688(12) 0.5125(4) 0.88300(11) 0.0581(6) Uani 1 1 d . . . . .
H6 H 0.486084 0.409047 0.882960 0.070 Uiso 1 1 calc R U . . .
C19 C 0.34252(14) -0.0616(3) 0.51380(12) 0.0590(6) Uani 1 1 d . . . . .
H19 H 0.318096 -0.141174 0.468906 0.071 Uiso 1 1 calc R U . . .
C22 C 0.24380(13) 0.7102(3) 0.67198(12) 0.0566(5) Uani 1 1 d . . . . .
H22 H 0.263000 0.850383 0.689916 0.068 Uiso 1 1 calc R U . . .
C11 C 0.68598(13) 0.7489(4) 0.65109(13) 0.0622(6) Uani 1 1 d . . . . .
H11 H 0.722608 0.827650 0.633125 0.075 Uiso 1 1 calc R U . . .
C3 C 0.64926(12) 0.8254(4) 0.88372(12) 0.0624(6) Uani 1 1 d . . . . .
H3 H 0.689399 0.930857 0.883857 0.075 Uiso 1 1 calc R U . . .
C26 C 0.14057(13) 0.4538(4) 0.64017(13) 0.0615(6) Uani 1 1 d . . . . .
H26 H 0.085915 0.410332 0.635244 0.074 Uiso 1 1 calc R U . . .
C5 C 0.56251(13) 0.6488(4) 0.94525(12) 0.0685(6) Uani 1 1 d . . . . .
H5 H 0.545736 0.635754 0.987535 0.082 Uiso 1 1 calc R U . . .
C4 C 0.62256(14) 0.8039(4) 0.94565(13) 0.0700(6) Uani 1 1 d . . . . .
H4 H 0.645352 0.894992 0.987919 0.084 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 N21 C26 115.31(18) . . ?
C25 C24 C23 116.05(17) . . ?
C25 C24 C15 121.54(16) . . ?
C23 C24 C15 122.38(16) . . ?
C20 C15 C16 118.63(17) . . ?
C20 C15 C24 119.06(15) . . ?
C16 C15 C24 122.31(16) . . ?
C17 C16 C15 118.46(17) . . ?
C17 C16 C14 120.24(16) . . ?
C15 C16 C14 121.14(16) . . ?
C8 C14 C16 128.73(18) . . ?
C10 C1 C9 121.28(18) . . ?
C10 C1 C2 129.60(18) . . ?
C9 C1 C2 109.11(16) . . ?
C13 C9 C1 119.05(18) . . ?
C13 C9 C8 132.75(18) . . ?
C1 C9 C8 108.09(16) . . ?
C14 C8 C7 122.93(17) . . ?
C14 C8 C9 130.99(17) . . ?
C7 C8 C9 105.35(15) . . ?
C3 C2 C7 120.55(19) . . ?
C3 C2 C1 131.26(18) . . ?
C7 C2 C1 108.17(16) . . ?
C6 C7 C2 120.06(18) . . ?
C6 C7 C8 130.71(18) . . ?
C2 C7 C8 109.18(16) . . ?
C22 C23 C24 119.43(18) . . ?
C19 C20 C15 121.48(18) . . ?
C26 C25 C24 120.17(18) . . ?
C11 C10 C1 118.79(19) . . ?
C9 C13 C12 119.29(19) . . ?
C18 C17 C16 121.90(18) . . ?
C11 C12 C13 121.0(2) . . ?
C19 C18 C17 119.39(19) . . ?
C5 C6 C7 118.87(19) . . ?
C18 C19 C20 120.1(2) . . ?
N21 C22 C23 124.80(19) . . ?
C12 C11 C10 120.6(2) . . ?
C2 C3 C4 118.8(2) . . ?
N21 C26 C25 124.24(19) . . ?
C4 C5 C6 121.0(2) . . ?
C5 C4 C3 120.7(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
N21 C22 1.330(2) . ?
N21 C26 1.336(3) . ?
C24 C25 1.386(2) . ?
C24 C23 1.392(2) . ?
C24 C15 1.486(2) . ?
C15 C20 1.395(2) . ?
C15 C16 1.408(2) . ?
C16 C17 1.396(2) . ?
C16 C14 1.477(2) . ?
C14 C8 1.341(2) . ?
C1 C10 1.382(3) . ?
C1 C9 1.407(2) . ?
C1 C2 1.464(3) . ?
C9 C13 1.387(2) . ?
C9 C8 1.488(2) . ?
C8 C7 1.482(2) . ?
C2 C3 1.383(3) . ?
C2 C7 1.400(2) . ?
C7 C6 1.386(3) . ?
C23 C22 1.377(3) . ?
C20 C19 1.378(3) . ?
C25 C26 1.373(3) . ?
C10 C11 1.382(3) . ?
C13 C12 1.390(3) . ?
C17 C18 1.378(3) . ?
C12 C11 1.380(3) . ?
C18 C19 1.374(3) . ?
C6 C5 1.382(3) . ?
C3 C4 1.385(3) . ?
C5 C4 1.379(3) . ?
