# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_UPS3491DB_MVB110_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1871614'
loop_
_audit_author_name
_audit_author_address
'Debasis Banerjee'
;Indian Institute of Technology Roorkee
India
;
_audit_update_record             
;
2018-10-05 deposited with the CCDC.	2019-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        (E)-2-(4-methylstyryl)quinoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N'
_chemical_formula_weight         245.31

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.9624(3)
_cell_length_b                   8.0092(4)
_cell_length_c                   28.9234(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1381.21(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    111
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.13

_exptl_crystal_description       niddle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   0.985
_exptl_transmission_factor_max   0.985
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_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 omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43155
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_av_R_equivalents  0.1158
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.408
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3417
_reflns_number_gt                1657
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    1.000

_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)+(0.1000P)²+0.5548P] 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_abs_structure_details 
;
 Flack x determined using 519 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   7.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3417
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1487
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.2304
_refine_ls_wR_factor_gt          0.1735
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.955
_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 0.5545(6) 0.6166(5) 0.39198(13) 0.0671(10) Uani 1 1 d . . . . .
C1 C -0.1106(13) 0.7375(8) 0.12721(17) 0.115(2) Uani 1 1 d . . . . .
H8 H -0.236065 0.662349 0.128027 0.172 Uiso 1 1 calc R U . . .
H1 H -0.013851 0.708041 0.101964 0.172 Uiso 1 1 calc R U . . .
H9 H -0.163624 0.849663 0.123096 0.172 Uiso 1 1 calc R U . . .
C2 C 0.0182(11) 0.7253(6) 0.17224(15) 0.0752(15) Uani 1 1 d . . . . .
C3 C 0.2289(11) 0.7963(6) 0.17828(19) 0.0840(17) Uani 1 1 d . . . . .
H7 H 0.295580 0.851844 0.153620 0.101 Uiso 1 1 calc R U . . .
C4 C 0.3417(10) 0.7866(7) 0.2197(2) 0.0834(15) Uani 1 1 d . . . . .
H12 H 0.481666 0.836857 0.222553 0.100 Uiso 1 1 calc R U . . .
C5 C 0.2512(8) 0.7043(6) 0.25681(16) 0.0676(12) Uani 1 1 d . . . . .
C6 C 0.3638(9) 0.6838(6) 0.3040(2) 0.0803(15) Uani 1 1 d . . . . .
H6 H 0.297364 0.609661 0.324656 0.096 Uiso 1 1 calc R U . . .
C7 C 0.5412(11) 0.7592(7) 0.3178(2) 0.0913(17) Uani 1 1 d . . . . .
H13 H 0.602618 0.840367 0.298553 0.110 Uiso 1 1 calc R U . . .
C8 C 0.6535(10) 0.7255(6) 0.36202(15) 0.0750(15) Uani 1 1 d . . . . .
C9 C 0.6731(7) 0.5805(5) 0.43120(14) 0.0549(10) Uani 1 1 d . . . . .
C10 C 0.8855(7) 0.6516(6) 0.44041(16) 0.0625(12) Uani 1 1 d . . . . .
C11 C 0.9999(9) 0.6056(7) 0.48137(19) 0.0805(15) Uani 1 1 d . . . . .
H3 H 1.139697 0.651148 0.488049 0.097 Uiso 1 1 calc R U . . .
C12 C 0.9031(12) 0.4931(8) 0.51120(19) 0.0937(19) Uani 1 1 d . . . . .
H2 H 0.976729 0.464059 0.538381 0.112 Uiso 1 1 calc R U . . .
C13 C 0.8618(11) 0.7984(7) 0.3706(2) 0.0891(17) Uani 1 1 d . . . . .
H4 H 0.922432 0.872607 0.349303 0.107 Uiso 1 1 calc R U . . .
C14 C 0.9720(10) 0.7634(7) 0.4082(2) 0.0864(16) Uani 1 1 d . . . . .
H5 H 1.110070 0.813757 0.413650 0.104 Uiso 1 1 calc R U . . .
C15 C -0.0712(9) 0.6401(6) 0.20968(16) 0.0724(13) Uani 1 1 d . . . . .
H10 H -0.210459 0.588675 0.206966 0.087 Uiso 1 1 calc R U . . .
C16 C 0.0433(8) 0.6310(6) 0.25058(16) 0.0691(13) Uani 1 1 d . . . . .
H11 H -0.020992 0.573308 0.275137 0.083 Uiso 1 1 calc R U . . .
C17 C 0.5855(9) 0.4648(6) 0.46259(16) 0.0726(13) Uani 1 1 d . . . . .
H14 H 0.447007 0.415804 0.456676 0.087 Uiso 1 1 calc R U . . .
C18 C 0.6980(12) 0.4231(7) 0.50114(18) 0.0900(17) Uani 1 1 d . . . . .
H15 H 0.636216 0.345621 0.521405 0.108 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 C8 1.364(6) . ?
N1 C9 1.368(5) . ?
C1 C2 1.515(7) . ?
C1 H8 0.9600 . ?
C1 H1 0.9600 . ?
C1 H9 0.9600 . ?
C2 C15 1.387(7) . ?
C2 C3 1.390(8) . ?
C3 C4 1.376(8) . ?
C3 H7 0.9300 . ?
C4 C5 1.371(7) . ?
C4 H12 0.9300 . ?
C5 C16 1.383(7) . ?
C5 C6 1.531(7) . ?
C6 C7 1.281(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.470(7) . ?
C7 H13 0.9300 . ?
C8 C13 1.395(8) . ?
C9 C17 1.399(6) . ?
C9 C10 1.414(6) . ?
C10 C14 1.391(7) . ?
C10 C11 1.416(6) . ?
C11 C12 1.374(8) . ?
C11 H3 0.9300 . ?
C12 C18 1.376(8) . ?
C12 H2 0.9300 . ?
C13 C14 1.301(7) . ?
C13 H4 0.9300 . ?
C14 H5 0.9300 . ?
C15 C16 1.368(6) . ?
C15 H10 0.9300 . ?
C16 H11 0.9300 . ?
C17 C18 1.343(7) . ?
C17 H14 0.9300 . ?
C18 H15 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
C8 N1 C9 116.0(4) . . ?
C2 C1 H8 109.5 . . ?
C2 C1 H1 109.5 . . ?
H8 C1 H1 109.5 . . ?
C2 C1 H9 109.5 . . ?
H8 C1 H9 109.5 . . ?
H1 C1 H9 109.5 . . ?
C15 C2 C3 116.8(5) . . ?
C15 C2 C1 120.5(6) . . ?
C3 C2 C1 122.7(5) . . ?
C4 C3 C2 121.9(5) . . ?
C4 C3 H7 119.1 . . ?
C2 C3 H7 119.1 . . ?
C5 C4 C3 121.1(6) . . ?
C5 C4 H12 119.5 . . ?
C3 C4 H12 119.5 . . ?
C4 C5 C16 117.1(5) . . ?
C4 C5 C6 125.3(5) . . ?
C16 C5 C6 117.6(5) . . ?
C7 C6 C5 126.0(6) . . ?
C7 C6 H6 117.0 . . ?
C5 C6 H6 117.0 . . ?
C6 C7 C8 124.0(6) . . ?
C6 C7 H13 118.0 . . ?
C8 C7 H13 118.0 . . ?
N1 C8 C13 122.7(5) . . ?
N1 C8 C7 118.3(5) . . ?
C13 C8 C7 119.0(5) . . ?
N1 C9 C17 119.0(4) . . ?
N1 C9 C10 122.3(4) . . ?
C17 C9 C10 118.6(4) . . ?
C14 C10 C9 117.7(5) . . ?
C14 C10 C11 123.3(5) . . ?
C9 C10 C11 119.0(5) . . ?
C12 C11 C10 119.6(5) . . ?
C12 C11 H3 120.2 . . ?
C10 C11 H3 120.2 . . ?
C11 C12 C18 120.5(5) . . ?
C11 C12 H2 119.8 . . ?
C18 C12 H2 119.8 . . ?
C14 C13 C8 120.6(5) . . ?
C14 C13 H4 119.7 . . ?
C8 C13 H4 119.7 . . ?
C13 C14 C10 120.7(6) . . ?
C13 C14 H5 119.6 . . ?
C10 C14 H5 119.6 . . ?
C16 C15 C2 120.6(5) . . ?
C16 C15 H10 119.7 . . ?
C2 C15 H10 119.7 . . ?
C15 C16 C5 122.5(5) . . ?
C15 C16 H11 118.7 . . ?
C5 C16 H11 118.7 . . ?
C18 C17 C9 121.1(5) . . ?
C18 C17 H14 119.4 . . ?
C9 C17 H14 119.4 . . ?
C17 C18 C12 121.2(6) . . ?
C17 C18 H15 119.4 . . ?
C12 C18 H15 119.4 . . ?

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
C15 C2 C3 C4 -1.7(7) . . . . ?
C1 C2 C3 C4 178.8(5) . . . . ?
C2 C3 C4 C5 0.8(8) . . . . ?
C3 C4 C5 C16 0.4(7) . . . . ?
C3 C4 C5 C6 178.9(5) . . . . ?
C4 C5 C6 C7 10.6(8) . . . . ?
C16 C5 C6 C7 -170.9(5) . . . . ?
C5 C6 C7 C8 -174.9(4) . . . . ?
C9 N1 C8 C13 -0.8(6) . . . . ?
C9 N1 C8 C7 175.6(4) . . . . ?
C6 C7 C8 N1 -5.2(7) . . . . ?
C6 C7 C8 C13 171.3(5) . . . . ?
C8 N1 C9 C17 -177.5(4) . . . . ?
C8 N1 C9 C10 0.1(6) . . . . ?
N1 C9 C10 C14 0.9(6) . . . . ?
C17 C9 C10 C14 178.5(4) . . . . ?
N1 C9 C10 C11 -178.8(4) . . . . ?
C17 C9 C10 C11 -1.2(6) . . . . ?
C14 C10 C11 C12 -179.5(5) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 C18 1.1(7) . . . . ?
N1 C8 C13 C14 0.5(8) . . . . ?
C7 C8 C13 C14 -175.9(5) . . . . ?
C8 C13 C14 C10 0.6(8) . . . . ?
C9 C10 C14 C13 -1.2(7) . . . . ?
C11 C10 C14 C13 178.4(5) . . . . ?
C3 C2 C15 C16 1.4(7) . . . . ?
C1 C2 C15 C16 -179.1(4) . . . . ?
C2 C15 C16 C5 -0.2(7) . . . . ?
C4 C5 C16 C15 -0.7(7) . . . . ?
C6 C5 C16 C15 -179.4(4) . . . . ?
N1 C9 C17 C18 178.7(4) . . . . ?
C10 C9 C17 C18 1.0(7) . . . . ?
C9 C17 C18 C12 0.2(8) . . . . ?
C11 C12 C18 C17 -1.2(8) . . . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.083



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/hexane'
