# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014



data_global
_journal_name_full               'Green Chemistry'
_journal_coden_cambridge         1048
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        M.Saha
_publ_contact_author_email       mthsaha2@gmail.com
loop_
_publ_author_name
R.Jamatia
M.Saha
'A. K. Pal'


data_ap-rj-35
#TrackingRef 'ap-rj-35.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 Cl2 N2'
_chemical_formula_weight         381.28

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'
Cl Cl 0.1484 0.1585 '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           ?
_symmetry_space_group_name_H-M   ?

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                   14.0976(12)
_cell_length_b                   10.0170(7)
_cell_length_c                   14.9301(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.746(11)
_cell_angle_gamma                90.00
_cell_volume                     1882.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9789
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         29.11
_reflns_number_total             4403
_reflns_number_gt                2719
_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)+(0.0533P)²+0.6039P] 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         4403
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
Cl18 Cl 0.95708(6) 1.11481(8) 0.58284(6) 0.0734(3) Uani 1 1 d . . .
Cl25 Cl 0.99534(6) 0.53143(11) 0.31828(6) 0.0865(3) Uani 1 1 d . . .
C3 C 0.59753(18) 0.4847(2) 0.37229(16) 0.0374(5) Uani 1 1 d . . .
C17 C 0.6705(2) 0.9544(2) 0.47732(18) 0.0456(6) Uani 1 1 d . . .
H17 H 0.6016 0.9855 0.4563 0.055 Uiso 1 1 calc R . .
C23 C 0.7915(2) 0.5888(3) 0.2711(2) 0.0565(7) Uani 1 1 d . . .
H23 H 0.7934 0.6452 0.2224 0.068 Uiso 1 1 calc R . .
N4 N 0.50381(15) 0.52431(19) 0.28046(14) 0.0437(5) Uani 1 1 d . . .
H4 H 0.5039 0.5194 0.2230 0.052 Uiso 1 1 calc R . .
N11 N 0.50619(15) 0.77780(18) 0.37253(14) 0.0406(5) Uani 1 1 d . . .
C16 C 0.7535(2) 1.0433(2) 0.51197(18) 0.0490(6) Uani 1 1 d . . .
H16 H 0.7406 1.1340 0.5142 0.059 Uiso 1 1 calc R . .
C26 C 0.5806(2) 0.3431(2) 0.40193(19) 0.0489(6) Uani 1 1 d . . .
H26A H 0.5127 0.3380 0.4020 0.073 Uiso 1 1 calc R . .
H26B H 0.6355 0.3227 0.4677 0.073 Uiso 1 1 calc R . .
H26C H 0.5831 0.2800 0.3546 0.073 Uiso 1 1 calc R . .
C15 C 0.8551(2) 0.9984(2) 0.54320(18) 0.0474(6) Uani 1 1 d . . .
C19 C 0.69615(19) 0.4937(2) 0.35538(17) 0.0389(5) Uani 1 1 d . . .
C10 C 0.41548(18) 0.6953(2) 0.33137(16) 0.0407(5) Uani 1 1 d . . .
C21 C 0.8783(2) 0.4345(3) 0.4044(2) 0.0543(7) Uani 1 1 d . . .
H21 H 0.9386 0.3861 0.4456 0.065 Uiso 1 1 calc R . .
C6 C 0.3193(2) 0.4990(3) 0.24799(19) 0.0554(7) Uani 1 1 d . . .
H6 H 0.3172 0.4152 0.2203 0.067 Uiso 1 1 calc R . .
C13 C 0.79260(19) 0.7758(2) 0.50852(19) 0.0479(6) Uani 1 1 d . . .
H13 H 0.8067 0.6851 0.5086 0.057 Uiso 1 1 calc R . .
C22 C 0.8794(2) 0.5175(3) 0.3320(2) 0.0542(7) Uani 1 1 d . . .
C20 C 0.7868(2) 0.4238(2) 0.41532(19) 0.0495(6) Uani 1 1 d . . .
H20 H 0.7862 0.3678 0.4647 0.059 Uiso 1 1 calc R . .
C12 C 0.68830(17) 0.8185(2) 0.47326(16) 0.0363(5) Uani 1 1 d . . .
C5 C 0.41374(18) 0.5705(2) 0.28864(16) 0.0423(5) Uani 1 1 d . . .
C2 C 0.60955(18) 0.5803(2) 0.45740(15) 0.0372(5) Uani 1 1 d . . .
H2A H 0.5571 0.5568 0.4800 0.045 Uiso 1 1 calc R . .
H2B H 0.6792 0.5670 0.5133 0.045 Uiso 1 1 calc R . .
C1 C 0.59699(18) 0.7260(2) 0.42963(16) 0.0363(5) Uani 1 1 d . . .
C9 C 0.3222(2) 0.7470(3) 0.32803(18) 0.0507(6) Uani 1 1 d . . .
H9 H 0.3225 0.8320 0.3532 0.061 Uiso 1 1 calc R . .
C14 C 0.8758(2) 0.8655(3) 0.5435(2) 0.0541(7) Uani 1 1 d . . .
H14 H 0.9453 0.8355 0.5670 0.065 Uiso 1 1 calc R . .
C24 C 0.6994(2) 0.5767(2) 0.28215(18) 0.0477(6) Uani 1 1 d . . .
H24 H 0.6391 0.6246 0.2402 0.057 Uiso 1 1 calc R . .
C8 C 0.2299(2) 0.6744(3) 0.2882(2) 0.0638(8) Uani 1 1 d . . .
H8 H 0.1688 0.7088 0.2885 0.077 Uiso 1 1 calc R . .
C7 C 0.2282(2) 0.5506(4) 0.2480(2) 0.0672(8) Uani 1 1 d . . .
H7 H 0.1656 0.5013 0.2207 0.081 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
Cl18 C15 1.735(2) . ?
Cl25 C22 1.741(3) . ?
C3 N4 1.467(3) . ?
C3 C19 1.523(3) . ?
C3 C26 1.536(3) . ?
C3 C2 1.539(3) . ?
C17 C16 1.372(3) . ?
C17 C12 1.391(3) . ?
C23 C22 1.363(4) . ?
C23 C24 1.387(3) . ?
N4 C5 1.408(3) . ?
N11 C1 1.286(3) . ?
N11 C10 1.410(3) . ?
C16 C15 1.368(3) . ?
C15 C14 1.363(3) . ?
C19 C20 1.377(3) . ?
C19 C24 1.391(3) . ?
C10 C9 1.393(3) . ?
C10 C5 1.398(3) . ?
C21 C22 1.369(4) . ?
C21 C20 1.375(3) . ?
C6 C7 1.384(4) . ?
C6 C5 1.388(3) . ?
C13 C14 1.379(3) . ?
C13 C12 1.388(3) . ?
C12 C1 1.478(3) . ?
C2 C1 1.505(3) . ?
C9 C8 1.370(4) . ?
C8 C7 1.373(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
N4 C3 C19 109.54(17) . . ?
N4 C3 C26 109.14(19) . . ?
C19 C3 C26 111.96(18) . . ?
N4 C3 C2 108.75(17) . . ?
C19 C3 C2 109.30(18) . . ?
C26 C3 C2 108.10(17) . . ?
C16 C17 C12 120.8(2) . . ?
C22 C23 C24 119.6(2) . . ?
C5 N4 C3 118.43(17) . . ?
C1 N11 C10 119.3(2) . . ?
C15 C16 C17 120.0(2) . . ?
C14 C15 C16 120.8(2) . . ?
C14 C15 Cl18 120.8(2) . . ?
C16 C15 Cl18 118.39(19) . . ?
C20 C19 C24 117.8(2) . . ?
C20 C19 C3 120.8(2) . . ?
C24 C19 C3 121.4(2) . . ?
C9 C10 C5 119.6(2) . . ?
C9 C10 N11 117.0(2) . . ?
C5 C10 N11 123.3(2) . . ?
C22 C21 C20 119.0(3) . . ?
C7 C6 C5 120.9(3) . . ?
C14 C13 C12 121.2(2) . . ?
C23 C22 C21 121.0(2) . . ?
C23 C22 Cl25 119.9(2) . . ?
C21 C22 Cl25 119.1(2) . . ?
C21 C20 C19 122.0(2) . . ?
C13 C12 C17 117.8(2) . . ?
C13 C12 C1 122.6(2) . . ?
C17 C12 C1 119.6(2) . . ?
C6 C5 C10 118.5(2) . . ?
C6 C5 N4 121.2(2) . . ?
C10 C5 N4 120.1(2) . . ?
C1 C2 C3 114.86(17) . . ?
N11 C1 C12 116.7(2) . . ?
N11 C1 C2 122.2(2) . . ?
C12 C1 C2 120.99(19) . . ?
C8 C9 C10 121.0(3) . . ?
C15 C14 C13 119.4(2) . . ?
C23 C24 C19 120.6(2) . . ?
C9 C8 C7 119.7(3) . . ?
C8 C7 C6 120.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.871
_diffrn_reflns_theta_full        29.11
_diffrn_measured_fraction_theta_full 0.871
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.045


_database_code_depnum_ccdc_archive 'CCDC 933681'
