# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_VC1715
_database_code_depnum_ccdc_archive 'CCDC 1504772'
_audit_update_record             
;
2016-09-17 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
'1,3-Bis[(E)-2-(methoxycarbonyl)-3-[6-(prop-2-ynyloxy)-naphthalen-2-yl]allyl]-1H-imidazol-3-ium chloride x 2CHCl3'
_chemical_formula_moiety         'C39 H33 N2 O6, 2(C H Cl3), Cl'
_chemical_formula_sum            'C41 H35 Cl7 N2 O6'
_chemical_formula_weight         899.86

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_H-M_alt        'C m'
_space_group_name_Hall           'C -2y'

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

_cell_length_a                   10.2450(13)
_cell_length_b                   25.069(2)
_cell_length_c                   8.5267(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.290(11)
_cell_angle_gamma                90
_cell_volume                     2122.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1800
_cell_measurement_theta_min      2.2019
_cell_measurement_theta_max      28.8975

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             924.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_T_min  0.57602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0827
_diffrn_reflns_number            8443
_diffrn_reflns_av_unetI/netI     0.0841
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.206
_diffrn_reflns_theta_max         28.961
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.789
_diffrn_reflns_point_group_measured_fraction_full 0.936
_reflns_number_total             4531
_reflns_number_gt                2570
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_max     0.686
_reflns_Friedel_fraction_full    0.872

_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1015P)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_abs_structure_details 
;
 Flack x determined using 811 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.04(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4531
_refine_ls_number_parameters     269
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2125
_refine_ls_wR_factor_gt          0.1747
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 1.0341(7) 0.5433(2) 1.0491(10) 0.0395(12) Uani 1 1 d . . . . .
C2 C 1.0530(9) 0.5269(3) 0.9008(10) 0.0480(16) Uani 1 1 d . . . . .
H2 H 1.0636 0.5489 0.8171 0.058 Uiso 1 1 calc R U . . .
C3 C 1.0262(11) 0.5000 1.1355(13) 0.042(2) Uani 1 2 d S T P . .
H3 H 1.0166 0.5000 1.2412 0.050 Uiso 1 2 calc R U P . .
C4 C 1.0169(9) 0.5982(3) 1.1009(11) 0.0474(16) Uani 1 1 d . . . . .
H4A H 1.0235 0.5982 1.2164 0.057 Uiso 1 1 calc R U . . .
H4B H 0.9273 0.6104 1.0468 0.057 Uiso 1 1 calc R U . . .
C5 C 1.1193(8) 0.6371(3) 1.0657(11) 0.0449(16) Uani 1 1 d . . . . .
C6 C 1.0893(9) 0.6779(3) 0.9651(11) 0.0500(17) Uani 1 1 d . . . . .
H6 H 1.1611 0.7008 0.9666 0.060 Uiso 1 1 calc R U . . .
C7 C 0.9614(9) 0.6935(3) 0.8502(11) 0.0480(17) Uani 1 1 d . . . . .
C8 C 0.9332(10) 0.7465(3) 0.8194(11) 0.0522(18) Uani 1 1 d . . . . .
H8 H 0.9941 0.7718 0.8739 0.063 Uiso 1 1 calc R U . . .
C9 C 0.8155(9) 0.7640(3) 0.7084(11) 0.0446(16) Uani 1 1 d . . . . .
C10 C 0.7849(10) 0.8195(3) 0.6800(12) 0.059(2) Uani 1 1 d . . . . .
H10 H 0.8425 0.8449 0.7394 0.070 Uiso 1 1 calc R U . . .
C11 C 0.6744(10) 0.8354(3) 0.5688(12) 0.060(2) Uani 1 1 d . . . . .
H11 H 0.6575 0.8715 0.5496 0.072 Uiso 1 1 calc R U . . .
C12 C 0.5837(9) 0.7968(3) 0.4809(11) 0.0509(18) Uani 1 1 d . . . . .
C13 C 0.6085(9) 0.7432(3) 0.5046(11) 0.0497(17) Uani 1 1 d . . . . .
H13 H 0.5491 0.7183 0.4454 0.060 Uiso 1 1 calc R U . . .
C14 C 0.7259(9) 0.7263(3) 0.6208(11) 0.0481(17) Uani 1 1 d . . . . .
C15 C 0.7548(10) 0.6713(3) 0.6496(12) 0.060(2) Uani 1 1 d . . . . .
H15 H 0.6956 0.6459 0.5925 0.072 Uiso 1 1 calc R U . . .
C16 C 0.8692(10) 0.6552(3) 0.7611(12) 0.064(2) Uani 1 1 d . . . . .
H16 H 0.8867 0.6190 0.7785 0.077 Uiso 1 1 calc R U . . .
C17 C 1.2595(9) 0.6323(3) 1.1654(12) 0.0551(18) Uani 1 1 d . . . . .
O1 O 1.3524(8) 0.6594(3) 1.1521(11) 0.0819(19) Uani 1 1 d . . . . .
O2 O 1.2707(7) 0.5921(2) 1.2713(10) 0.0646(14) Uani 1 1 d . . . . .
C18 C 1.4048(12) 0.5840(4) 1.3832(14) 0.089(3) Uani 1 1 d . . . . .
H18A H 1.4327 0.6162 1.4429 0.133 Uiso 1 1 calc R U . . .
H18B H 1.4689 0.5749 1.3222 0.133 Uiso 1 1 calc R U . . .
H18C H 1.3999 0.5556 1.4571 0.133 Uiso 1 1 calc R U . . .
O3 O 0.4748(7) 0.81818(19) 0.3701(10) 0.0579(13) Uani 1 1 d . . . . .
C19 C 0.3811(10) 0.7807(3) 0.2797(12) 0.0557(19) Uani 1 1 d . . . . .
H19A H 0.3566 0.7547 0.3517 0.067 Uiso 1 1 calc R U . . .
H19B H 0.4206 0.7620 0.2030 0.067 Uiso 1 1 calc R U . . .
C20 C 0.2632(10) 0.8104(3) 0.1950(12) 0.0579(19) Uani 1 1 d . . . . .
C21 C 0.1637(12) 0.8327(4) 0.1322(14) 0.084(3) Uani 1 1 d . . . . .
H21 H 0.0847 0.8505 0.0824 0.100 Uiso 1 1 calc R U . . .
C26 C 0.8124(16) 0.5000 0.4535(19) 0.086(4) Uani 1 2 d S T P . .
H26 H 0.9086 0.5000 0.5080 0.104 Uiso 1 2 calc R U P . .
Cl3 Cl 0.7795(7) 0.55727(16) 0.3441(9) 0.1522(18) Uani 1 1 d . . . . .
Cl4 Cl 0.7218(7) 0.5000 0.6051(9) 0.141(2) Uani 1 2 d S T P . .
C27 C 0.4438(4) 0.5000 0.8619(8) 0.106(5) Uani 1 2 d DS T P . .
H27A H 0.3626 0.5000 0.7725 0.127 Uiso 0.900(6) 2 calc R U P A 1
H27B H 0.4203 0.5000 0.7433 0.127 Uiso 0.100(6) 2 calc R U P A 2
Cl1 Cl 0.5360(5) 0.55702(15) 0.8442(9) 0.1417(17) Uani 0.900(6) 1 d D . P A 1
Cl2 Cl 0.3933(8) 0.5000 1.0423(8) 0.194(4) Uani 0.900(6) 2 d DS T P A 1
Cl1B Cl 0.425(5) 0.5644(7) 0.929(5) 0.1417(17) Uani 0.100(6) 1 d D . P A 2
Cl2B Cl 0.6184(6) 0.5000 0.931(5) 0.194(4) Uani 0.100(6) 2 d DS T P A 2
Cl5 Cl 1.1523(6) 0.5000 1.5515(8) 0.0761(10) Uani 1 2 d S T P . .


_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 C3 1.324(7) . ?
N1 C2 1.388(8) . ?
N1 C4 1.470(8) . ?
C2 C2 1.350(14) 2_565 ?
C3 N1 1.324(7) 2_565 ?
C4 C5 1.516(10) . ?
C5 C6 1.321(9) . ?
C5 C17 1.483(10) . ?
C6 C7 1.482(10) . ?
C7 C8 1.369(10) . ?
C7 C16 1.429(11) . ?
C8 C9 1.407(10) . ?
C9 C14 1.397(9) . ?
C9 C10 1.434(9) . ?
C10 C11 1.345(11) . ?
C11 C12 1.420(10) . ?
C12 C13 1.373(10) . ?
C12 O3 1.380(9) . ?
C13 C14 1.421(9) . ?
C14 C15 1.419(10) . ?
C15 C16 1.375(10) . ?
C17 O1 1.198(9) . ?
C17 O2 1.339(9) . ?
O2 C18 1.481(11) . ?
O3 C19 1.425(9) . ?
C19 C20 1.450(11) . ?
C20 C21 1.170(12) . ?
C26 Cl3 1.700(9) 2_565 ?
C26 Cl3 1.700(9) . ?
C26 Cl4 1.769(15) . ?
C27 Cl2B 1.7400(15) . ?
C27 Cl1B 1.7398(14) 2_565 ?
C27 Cl1B 1.7398(14) . ?
C27 Cl2 1.7402(14) . ?
C27 Cl1 1.7402(14) . ?
C27 Cl1 1.7403(14) 2_565 ?
Cl1B Cl2B 2.55(4) . ?
Cl2B Cl1B 2.55(4) 2_565 ?

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
C3 N1 C2 107.9(5) . . ?
C3 N1 C4 124.9(5) . . ?
C2 N1 C4 127.2(5) . . ?
C2 C2 N1 107.2(3) 2_565 . ?
N1 C3 N1 109.9(7) 2_565 . ?
N1 C4 C5 113.8(5) . . ?
C6 C5 C17 118.2(7) . . ?
C6 C5 C4 124.4(7) . . ?
C17 C5 C4 117.0(6) . . ?
C5 C6 C7 131.3(7) . . ?
C8 C7 C16 118.0(7) . . ?
C8 C7 C6 119.6(6) . . ?
C16 C7 C6 122.2(6) . . ?
C7 C8 C9 122.5(7) . . ?
C14 C9 C8 119.3(6) . . ?
C14 C9 C10 118.5(7) . . ?
C8 C9 C10 122.1(7) . . ?
C11 C10 C9 121.2(7) . . ?
C10 C11 C12 119.8(7) . . ?
C13 C12 O3 124.8(7) . . ?
C13 C12 C11 121.0(7) . . ?
O3 C12 C11 114.2(6) . . ?
C12 C13 C14 119.3(6) . . ?
C9 C14 C15 118.9(6) . . ?
C9 C14 C13 120.1(6) . . ?
C15 C14 C13 121.0(6) . . ?
C16 C15 C14 120.8(7) . . ?
C15 C16 C7 120.5(7) . . ?
O1 C17 O2 123.7(7) . . ?
O1 C17 C5 125.4(7) . . ?
O2 C17 C5 111.0(7) . . ?
C17 O2 C18 116.7(7) . . ?
C12 O3 C19 115.9(6) . . ?
O3 C19 C20 107.3(6) . . ?
C21 C20 C19 176.0(10) . . ?
Cl3 C26 Cl3 115.3(9) 2_565 . ?
Cl3 C26 Cl4 109.4(6) 2_565 . ?
Cl3 C26 Cl4 109.4(6) . . ?
Cl2B C27 Cl1B 94.3(18) . 2_565 ?
Cl2B C27 Cl1B 94.3(18) . . ?
Cl1B C27 Cl1B 136(3) 2_565 . ?
Cl2 C27 Cl1 111.3(4) . . ?
Cl2 C27 Cl1 111.3(4) . 2_565 ?
Cl1 C27 Cl1 110.4(4) . 2_565 ?
C27 Cl1B Cl2B 42.9(9) . . ?
C27 Cl2B Cl1B 42.9(9) . 2_565 ?
C27 Cl2B Cl1B 42.9(9) . . ?
Cl1B Cl2B Cl1B 78.6(19) 2_565 . ?

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
C3 N1 C2 C2 1.4(6) . . . 2_565 ?
C4 N1 C2 C2 -175.1(5) . . . 2_565 ?
C2 N1 C3 N1 -2.3(11) . . . 2_565 ?
C4 N1 C3 N1 174.3(5) . . . 2_565 ?
C3 N1 C4 C5 136.7(8) . . . . ?
C2 N1 C4 C5 -47.4(9) . . . . ?
N1 C4 C5 C6 115.7(7) . . . . ?
N1 C4 C5 C17 -71.6(7) . . . . ?
C17 C5 C6 C7 179.5(7) . . . . ?
C4 C5 C6 C7 -7.9(12) . . . . ?
C5 C6 C7 C8 147.7(8) . . . . ?
C5 C6 C7 C16 -36.5(12) . . . . ?
C16 C7 C8 C9 2.2(11) . . . . ?
C6 C7 C8 C9 178.2(7) . . . . ?
C7 C8 C9 C14 -2.6(11) . . . . ?
C7 C8 C9 C10 178.3(7) . . . . ?
C14 C9 C10 C11 -1.6(11) . . . . ?
C8 C9 C10 C11 177.4(7) . . . . ?
C9 C10 C11 C12 1.9(12) . . . . ?
C10 C11 C12 C13 -1.6(12) . . . . ?
C10 C11 C12 O3 -179.7(7) . . . . ?
O3 C12 C13 C14 178.9(6) . . . . ?
C11 C12 C13 C14 0.9(11) . . . . ?
C8 C9 C14 C15 1.6(10) . . . . ?
C10 C9 C14 C15 -179.3(7) . . . . ?
C8 C9 C14 C13 -178.1(6) . . . . ?
C10 C9 C14 C13 0.9(10) . . . . ?
C12 C13 C14 C9 -0.6(10) . . . . ?
C12 C13 C14 C15 179.7(7) . . . . ?
C9 C14 C15 C16 -0.4(12) . . . . ?
C13 C14 C15 C16 179.4(8) . . . . ?
C14 C15 C16 C7 0.0(13) . . . . ?
C8 C7 C16 C15 -0.9(12) . . . . ?
C6 C7 C16 C15 -176.8(8) . . . . ?
C6 C5 C17 O1 -7.6(11) . . . . ?
C4 C5 C17 O1 179.3(7) . . . . ?
C6 C5 C17 O2 174.1(7) . . . . ?
C4 C5 C17 O2 1.0(8) . . . . ?
O1 C17 O2 C18 3.8(12) . . . . ?
C5 C17 O2 C18 -177.8(7) . . . . ?
C13 C12 O3 C19 2.1(10) . . . . ?
C11 C12 O3 C19 -179.8(7) . . . . ?
C12 O3 C19 C20 169.1(6) . . . . ?
Cl1B C27 Cl1B Cl2B 101(4) 2_565 . . . ?
Cl2 C27 Cl1B Cl2B 101.0(18) . . . . ?
Cl1 C27 Cl1B Cl2B -45(2) . . . . ?
Cl1 C27 Cl1B Cl2B 7(3) 2_565 . . . ?
Cl1B C27 Cl2B Cl1B 137(3) . . . 2_565 ?
Cl2 C27 Cl2B Cl1B 68.6(14) . . . 2_565 ?
Cl1 C27 Cl2B Cl1B 176.5(17) . . . 2_565 ?
Cl1 C27 Cl2B Cl1B -39.3(18) 2_565 . . 2_565 ?
Cl1B C27 Cl2B Cl1B -137(3) 2_565 . . . ?
Cl2 C27 Cl2B Cl1B -68.6(14) . . . . ?
Cl1 C27 Cl2B Cl1B 39.3(18) . . . . ?
Cl1 C27 Cl2B Cl1B -176.5(17) 2_565 . . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-4

