# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_123
_database_code_depnum_ccdc_archive 'CCDC 1850300'
loop_
_audit_author_name
_audit_author_address
'Laxmi Raman Adil'
;IIT Guwahati
India
;
_audit_update_record             
;
2018-06-19 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 N'
_chemical_formula_sum            'C25 H17 N'
_chemical_formula_weight         331.40

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3412(4)
_cell_length_b                   20.3704(9)
_cell_length_c                   10.3467(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.383(3)
_cell_angle_gamma                90.00
_cell_volume                     1750.29(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2539
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      20.18

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696.0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18868
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3102
_reflns_number_gt                1797
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3102
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1670
_refine_ls_wR_factor_gt          0.1366
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1472(3) 0.41298(14) -0.1946(2) 0.1030(7) Uani 1 1 d . . .
C6 C 0.2478(2) 0.50452(10) 0.1783(2) 0.0632(6) Uani 1 1 d . . .
C14 C 0.1091(2) 0.64598(9) 0.60058(19) 0.0596(5) Uani 1 1 d . . .
C25 C 0.3343(2) 0.65358(9) 0.7531(2) 0.0607(5) Uani 1 1 d . . .
C19 C 0.0678(2) 0.68257(9) 0.70682(19) 0.0615(6) Uani 1 1 d . . .
C13 C 0.2790(2) 0.62632(9) 0.6248(2) 0.0607(5) Uani 1 1 d . . .
C9 C 0.3267(3) 0.56322(11) 0.4221(2) 0.0696(6) Uani 1 1 d . . .
C3 C 0.2108(2) 0.47390(11) 0.0495(2) 0.0653(6) Uani 1 1 d . . .
C7 C 0.1910(3) 0.48114(11) 0.2880(2) 0.0810(7) Uani 1 1 d . . .
H7 H 0.1243 0.4445 0.2823 0.097 Uiso 1 1 calc R . .
C24 C 0.4825(3) 0.64929(10) 0.8254(2) 0.0745(6) Uani 1 1 d . . .
H24 H 0.5673 0.6268 0.7932 0.089 Uiso 1 1 calc R . .
C12 C 0.3724(3) 0.59352(10) 0.5495(2) 0.0728(6) Uani 1 1 d . . .
H12 H 0.4799 0.5892 0.5814 0.087 Uiso 1 1 calc R . .
C20 C 0.2080(3) 0.68652(9) 0.8026(2) 0.0630(6) Uani 1 1 d . . .
C15 C -0.0038(3) 0.63691(10) 0.4948(2) 0.0687(6) Uani 1 1 d . . .
H15 H 0.0223 0.6131 0.4230 0.082 Uiso 1 1 calc R . .
C2 C 0.1161(3) 0.41808(12) 0.0309(2) 0.0807(7) Uani 1 1 d . . .
H2 H 0.0709 0.3992 0.1009 0.097 Uiso 1 1 calc R . .
C16 C -0.1547(3) 0.66357(11) 0.4976(2) 0.0778(7) Uani 1 1 d . . .
H16 H -0.2308 0.6576 0.4270 0.093 Uiso 1 1 calc R . .
C18 C -0.0847(3) 0.70920(10) 0.7088(2) 0.0771(7) Uani 1 1 d . . .
H18 H -0.1117 0.7334 0.7798 0.093 Uiso 1 1 calc R . .
C8 C 0.2289(3) 0.50989(11) 0.4073(2) 0.0845(7) Uani 1 1 d . . .
H8 H 0.1863 0.4924 0.4797 0.101 Uiso 1 1 calc R . .
C23 C 0.5023(3) 0.67867(12) 0.9453(2) 0.0869(7) Uani 1 1 d . . .
H23 H 0.6016 0.6764 0.9941 0.104 Uiso 1 1 calc R . .
C17 C -0.1956(3) 0.69906(11) 0.6034(3) 0.0813(7) Uani 1 1 d . . .
H17 H -0.2989 0.7163 0.6034 0.098 Uiso 1 1 calc R . .
C21 C 0.2283(3) 0.71547(11) 0.9240(2) 0.0814(7) Uani 1 1 d . . .
H21 H 0.1433 0.7372 0.9576 0.098 Uiso 1 1 calc R . .
C22 C 0.3761(3) 0.71159(11) 0.9941(2) 0.0910(8) Uani 1 1 d . . .
H22 H 0.3915 0.7313 1.0754 0.109 Uiso 1 1 calc R . .
C4 C 0.2683(3) 0.49817(13) -0.0604(2) 0.0959(8) Uani 1 1 d . . .
H4 H 0.3305 0.5361 -0.0562 0.115 Uiso 1 1 calc R . .
C11 C 0.3459(4) 0.55878(15) 0.1934(3) 0.1147(11) Uani 1 1 d . . .
H11 H 0.3868 0.5769 0.1208 0.138 Uiso 1 1 calc R . .
C10 C 0.3851(4) 0.58687(15) 0.3128(3) 0.1169(10) Uani 1 1 d . . .
H10 H 0.4534 0.6230 0.3191 0.140 Uiso 1 1 calc R . .
C1 C 0.0887(3) 0.39056(13) -0.0899(3) 0.0933(8) Uani 1 1 d . . .
H1 H 0.0241 0.3533 -0.0982 0.112 Uiso 1 1 calc R . .
C5 C 0.2344(4) 0.46665(19) -0.1767(3) 0.1169(10) Uani 1 1 d . . .
H5 H 0.2765 0.4846 -0.2489 0.140 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 C1 1.312(3) . ?
N1 C5 1.317(4) . ?
C6 C7 1.356(3) . ?
C6 C11 1.375(3) . ?
C6 C3 1.478(3) . ?
C14 C15 1.388(3) . ?
C14 C19 1.398(3) . ?
C14 C13 1.471(3) . ?
C25 C24 1.386(3) . ?
C25 C20 1.387(3) . ?
C25 C13 1.473(3) . ?
C19 C18 1.385(3) . ?
C19 C20 1.463(3) . ?
C13 C12 1.332(3) . ?
C9 C8 1.359(3) . ?
C9 C10 1.361(3) . ?
C9 C12 1.473(3) . ?
C3 C4 1.368(3) . ?
C3 C2 1.388(3) . ?
C7 C8 1.376(3) . ?
C24 C23 1.373(3) . ?
C20 C21 1.383(3) . ?
C15 C16 1.374(3) . ?
C2 C1 1.369(3) . ?
C16 C17 1.380(3) . ?
C18 C17 1.378(3) . ?
C23 C22 1.384(3) . ?
C21 C22 1.372(3) . ?
C4 C5 1.369(3) . ?
C11 C10 1.372(3) . ?

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
C1 N1 C5 114.6(2) . . ?
C7 C6 C11 116.0(2) . . ?
C7 C6 C3 123.1(2) . . ?
C11 C6 C3 120.9(2) . . ?
C15 C14 C19 119.49(19) . . ?
C15 C14 C13 132.0(2) . . ?
C19 C14 C13 108.42(18) . . ?
C24 C25 C20 120.07(19) . . ?
C24 C25 C13 130.6(2) . . ?
C20 C25 C13 109.30(18) . . ?
C18 C19 C14 121.00(19) . . ?
C18 C19 C20 130.2(2) . . ?
C14 C19 C20 108.78(18) . . ?
C12 C13 C14 130.1(2) . . ?
C12 C13 C25 124.38(19) . . ?
C14 C13 C25 105.44(18) . . ?
C8 C9 C10 116.6(2) . . ?
C8 C9 C12 122.6(2) . . ?
C10 C9 C12 120.8(2) . . ?
C4 C3 C2 114.8(2) . . ?
C4 C3 C6 122.5(2) . . ?
C2 C3 C6 122.6(2) . . ?
C6 C7 C8 122.1(2) . . ?
C23 C24 C25 119.1(2) . . ?
C13 C12 C9 128.1(2) . . ?
C21 C20 C25 120.6(2) . . ?
C21 C20 C19 131.4(2) . . ?
C25 C20 C19 108.05(18) . . ?
C16 C15 C14 119.1(2) . . ?
C1 C2 C3 120.4(2) . . ?
C15 C16 C17 121.3(2) . . ?
C17 C18 C19 118.6(2) . . ?
C9 C8 C7 121.8(2) . . ?
C24 C23 C22 120.7(2) . . ?
C18 C17 C16 120.6(2) . . ?
C22 C21 C20 118.8(2) . . ?
C21 C22 C23 120.8(2) . . ?
C3 C4 C5 120.1(3) . . ?
C10 C11 C6 121.7(2) . . ?
C9 C10 C11 121.8(2) . . ?
N1 C1 C2 124.6(3) . . ?
N1 C5 C4 125.4(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.031
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3-PN_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1850519'
loop_
_audit_author_name
_audit_author_address
'LAXMI RAMAN ADIL'
;IIT GUWAHATI
India
;
_audit_update_record             
;
2018-06-20 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H19 N'
_chemical_formula_sum            'C25 H19 N'
_chemical_formula_weight         333.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   5.7544(7)
_cell_length_b                   11.1791(13)
_cell_length_c                   28.221(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.062(2)
_cell_angle_gamma                90
_cell_volume                     1808.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      22.13

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus seald tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58468
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.449
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3173
_reflns_number_gt                2626
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²+0.2151P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3173
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.3669(2) 0.75126(13) 0.29352(5) 0.0697(4) Uani 1 1 d . . . . .
C002 C 0.3297(2) 0.24000(11) 0.44202(4) 0.0444(3) Uani 1 1 d . . . . .
C003 C 0.8568(2) 0.48527(11) 0.32286(4) 0.0477(3) Uani 1 1 d . . . . .
C004 C 0.2547(2) 0.18835(11) 0.39426(5) 0.0469(3) Uani 1 1 d . . . . .
C005 C 1.0310(2) 0.57650(12) 0.31180(4) 0.0485(3) Uani 1 1 d . . . . .
C006 C 0.5178(2) 0.31518(11) 0.34546(4) 0.0492(3) Uani 1 1 d . . . . .
C007 C 0.0748(2) 0.09280(11) 0.39342(4) 0.0472(3) Uani 1 1 d . . . . .
C008 C 0.7866(2) 0.39339(12) 0.29138(5) 0.0509(3) Uani 1 1 d . . . . .
H008 H 0.852742 0.387128 0.262586 0.061 Uiso 1 1 calc R U . . .
C009 C 0.3449(2) 0.22322(12) 0.35404(5) 0.0523(3) Uani 1 1 d . . . . .
H009 H 0.287319 0.181660 0.326964 0.063 Uiso 1 1 calc R U . . .
C00A C 0.6205(2) 0.31190(12) 0.30242(5) 0.0513(3) Uani 1 1 d . . . . .
H00A H 0.574913 0.252529 0.280450 0.062 Uiso 1 1 calc R U . . .
C00B C 0.1873(2) 0.31941(12) 0.46350(5) 0.0540(3) Uani 1 1 d . . . . .
H00B H 0.042537 0.339511 0.448337 0.065 Uiso 1 1 calc R U . . .
C00C C 1.2098(2) 0.55248(14) 0.28322(5) 0.0562(4) Uani 1 1 d . . . . .
H00C H 1.221676 0.477663 0.269228 0.067 Uiso 1 1 calc R U . . .
C00D C -0.0873(3) 0.07641(13) 0.35434(5) 0.0575(4) Uani 1 1 d . . . . .
H00D H -0.080401 0.124956 0.327742 0.069 Uiso 1 1 calc R U . . .
C00E C 0.0571(3) 0.01779(12) 0.43238(5) 0.0553(4) Uani 1 1 d . . . . .
H00E H 0.162642 0.026256 0.459077 0.066 Uiso 1 1 calc R U . . .
C00F C 0.7522(3) 0.49018(13) 0.36545(5) 0.0574(4) Uani 1 1 d . . . . .
H00F H 0.794451 0.551025 0.386982 0.069 Uiso 1 1 calc R U . . .
C00G C 0.5883(3) 0.40777(13) 0.37664(5) 0.0582(4) Uani 1 1 d . . . . .
H00G H 0.523223 0.413846 0.405560 0.070 Uiso 1 1 calc R U . . .
C00H C 0.5411(2) 0.20989(14) 0.46590(5) 0.0593(4) Uani 1 1 d . . . . .
H00H H 0.638752 0.155904 0.452315 0.071 Uiso 1 1 calc R U . . .
C00I C -0.1142(3) -0.06892(13) 0.43215(5) 0.0612(4) Uani 1 1 d . . . . .
H00I H -0.122065 -0.118185 0.458514 0.073 Uiso 1 1 calc R U . . .
C00J C 1.3701(2) 0.64144(16) 0.27581(5) 0.0642(4) Uani 1 1 d . . . . .
H00J H 1.489482 0.622677 0.256925 0.077 Uiso 1 1 calc R U . . .
C00K C 1.0248(3) 0.69189(13) 0.32975(6) 0.0634(4) Uani 1 1 d . . . . .
H00K H 0.906616 0.713962 0.348452 0.076 Uiso 1 1 calc R U . . .
C00L C 0.2580(3) 0.36922(14) 0.50727(5) 0.0633(4) Uani 1 1 d . . . . .
H00L H 0.161420 0.423346 0.521075 0.076 Uiso 1 1 calc R U . . .
C00M C 0.4686(3) 0.33942(14) 0.53033(5) 0.0619(4) Uani 1 1 d . . . . .
H00M H 0.516186 0.373258 0.559693 0.074 Uiso 1 1 calc R U . . .
C00N C -0.2732(3) -0.08289(13) 0.39319(6) 0.0627(4) Uani 1 1 d . . . . .
H00N H -0.389528 -0.140651 0.393211 0.075 Uiso 1 1 calc R U . . .
C00O C -0.2581(3) -0.01039(14) 0.35424(6) 0.0648(4) Uani 1 1 d . . . . .
H00O H -0.363696 -0.019877 0.327607 0.078 Uiso 1 1 calc R U . . .
C00P C 0.6090(3) 0.25919(15) 0.50979(6) 0.0664(4) Uani 1 1 d . . . . .
H00P H 0.751561 0.237705 0.525587 0.080 Uiso 1 1 calc R U . . .
C00Q C 1.1927(3) 0.77393(16) 0.32000(6) 0.0720(4) Uani 1 1 d . . . . .
H00Q H 1.183339 0.850224 0.332827 0.086 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C00Q 1.327(2) . ?
N1 C00J 1.326(2) . ?
C002 C00H 1.3796(19) . ?
C002 C00B 1.3836(18) . ?
C002 C004 1.4944(18) . ?
C003 C00F 1.3919(18) . ?
C003 C008 1.3945(18) . ?
C003 C005 1.4824(19) . ?
C004 C009 1.3465(18) . ?
C004 C007 1.4862(19) . ?
C005 C00K 1.388(2) . ?
C005 C00C 1.3882(18) . ?
C006 C00G 1.3956(19) . ?
C006 C00A 1.3974(18) . ?
C006 C009 1.4656(19) . ?
C007 C00D 1.3924(19) . ?
C007 C00E 1.3936(19) . ?
C008 C00A 1.3759(19) . ?
C008 H008 0.9300 . ?
C009 H009 0.9300 . ?
C00A H00A 0.9300 . ?
C00B C00L 1.383(2) . ?
C00B H00B 0.9300 . ?
C00C C00J 1.385(2) . ?
C00C H00C 0.9300 . ?
C00D C00O 1.381(2) . ?
C00D H00D 0.9300 . ?
C00E C00I 1.382(2) . ?
C00E H00E 0.9300 . ?
C00F C00G 1.3749(19) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00H C00P 1.380(2) . ?
C00H H00H 0.9300 . ?
C00I C00N 1.376(2) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00K C00Q 1.378(2) . ?
C00K H00K 0.9300 . ?
C00L C00M 1.365(2) . ?
C00L H00L 0.9300 . ?
C00M C00P 1.370(2) . ?
C00M H00M 0.9300 . ?
C00N C00O 1.375(2) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?

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
C00Q N1 C00J 115.17(14) . . ?
C00H C002 C00B 118.24(12) . . ?
C00H C002 C004 121.21(12) . . ?
C00B C002 C004 120.54(12) . . ?
C00F C003 C008 117.13(12) . . ?
C00F C003 C005 120.44(12) . . ?
C008 C003 C005 122.41(11) . . ?
C009 C004 C007 120.95(12) . . ?
C009 C004 C002 123.12(12) . . ?
C007 C004 C002 115.93(11) . . ?
C00K C005 C00C 115.87(13) . . ?
C00K C005 C003 121.53(12) . . ?
C00C C005 C003 122.60(13) . . ?
C00G C006 C00A 116.47(12) . . ?
C00G C006 C009 125.45(12) . . ?
C00A C006 C009 118.07(12) . . ?
C00D C007 C00E 117.07(13) . . ?
C00D C007 C004 121.62(12) . . ?
C00E C007 C004 121.29(12) . . ?
C00A C008 C003 120.77(12) . . ?
C00A C008 H008 119.6 . . ?
C003 C008 H008 119.6 . . ?
C004 C009 C006 131.30(13) . . ?
C004 C009 H009 114.3 . . ?
C006 C009 H009 114.3 . . ?
C008 C00A C006 122.34(13) . . ?
C008 C00A H00A 118.8 . . ?
C006 C00A H00A 118.8 . . ?
C00L C00B C002 120.73(13) . . ?
C00L C00B H00B 119.6 . . ?
C002 C00B H00B 119.6 . . ?
C00J C00C C005 119.10(14) . . ?
C00J C00C H00C 120.4 . . ?
C005 C00C H00C 120.4 . . ?
C00O C00D C007 121.41(14) . . ?
C00O C00D H00D 119.3 . . ?
C007 C00D H00D 119.3 . . ?
C00I C00E C007 121.34(14) . . ?
C00I C00E H00E 119.3 . . ?
C007 C00E H00E 119.3 . . ?
C00G C00F C003 121.98(13) . . ?
C00G C00F H00F 119.0 . . ?
C003 C00F H00F 119.0 . . ?
C00F C00G C006 121.29(12) . . ?
C00F C00G H00G 119.4 . . ?
C006 C00G H00G 119.4 . . ?
C00P C00H C002 120.56(13) . . ?
C00P C00H H00H 119.7 . . ?
C002 C00H H00H 119.7 . . ?
C00N C00I C00E 120.47(14) . . ?
C00N C00I H00I 119.8 . . ?
C00E C00I H00I 119.8 . . ?
N1 C00J C00C 125.20(14) . . ?
N1 C00J H00J 117.4 . . ?
C00C C00J H00J 117.4 . . ?
C00Q C00K C005 120.31(14) . . ?
C00Q C00K H00K 119.8 . . ?
C005 C00K H00K 119.8 . . ?
C00M C00L C00B 120.41(14) . . ?
C00M C00L H00L 119.8 . . ?
C00B C00L H00L 119.8 . . ?
C00L C00M C00P 119.35(14) . . ?
C00L C00M H00M 120.3 . . ?
C00P C00M H00M 120.3 . . ?
C00O C00N C00I 119.18(14) . . ?
C00O C00N H00N 120.4 . . ?
C00I C00N H00N 120.4 . . ?
C00N C00O C00D 120.52(15) . . ?
C00N C00O H00O 119.7 . . ?
C00D C00O H00O 119.7 . . ?
C00M C00P C00H 120.69(14) . . ?
C00M C00P H00P 119.7 . . ?
C00H C00P H00P 119.7 . . ?
N1 C00Q C00K 124.31(16) . . ?
N1 C00Q H00Q 117.8 . . ?
C00K C00Q H00Q 117.8 . . ?

_refine_diff_density_max         0.100
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.034


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_5475
_database_code_depnum_ccdc_archive 'CCDC 1941127'
loop_
_audit_author_name
_audit_author_address
'laxmi raman adil'
;IIT GUWAHATI 
India
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4-(2-((9H-fluoren-9-ylidene)methyl)phenyl)pyridine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 N'
_chemical_formula_weight         331.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   16.8722(15)
_cell_length_b                   6.0689(4)
_cell_length_c                   18.7149(19)
_cell_angle_alpha                90
_cell_angle_beta                 110.549(11)
_cell_angle_gamma                90
_cell_volume                     1794.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1982
_cell_measurement_theta_min      3.5450
_cell_measurement_theta_max      25.7540

_exptl_crystal_description       blcok
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6493
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.266
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.048
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3183
_reflns_number_gt                2105
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3183
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_ref         0.3373
_refine_ls_wR_factor_gt          0.2526
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_restrained_S_all      1.185
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 . ?

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 . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.094


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1PON-2
_database_code_depnum_ccdc_archive 'CCDC 1938858'
loop_
_audit_author_name
_audit_author_address
'laxmi raman adil'
;IIT GUWAHATI 
India
;
_audit_update_record             
;
2019-07-06 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
4-(2-((9H-fluoren-9-ylidene)methyl)phenyl)pyridine
_chemical_name_common            
4-(2-((9H-fluoren-9-ylidene)methyl)phenyl)pyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 N'
_chemical_formula_sum            'C25 H17 N'
_chemical_formula_weight         331.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   16.8262(9)
_cell_length_b                   6.0687(3)
_cell_length_c                   18.6754(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.396(6)
_cell_angle_gamma                90
_cell_volume                     1787.45(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1524
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      20.51

_exptl_crystal_description       rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7893
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.327
_diffrn_reflns_theta_max         28.948
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4110
_reflns_number_gt                2500
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.0665P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4110
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1382
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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) . ?

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) . . ?

_refine_diff_density_max         0.139
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
