# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1488168'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-08-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
2-chloro-6-(4-methoxyphenyl)-5-methylpyridine-3,4-dicarbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 Cl N3 O'
_chemical_formula_sum            'C15 H10 Cl N3 O'
_chemical_formula_weight         283.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   17.6640(9)
_cell_length_b                   7.2940(3)
_cell_length_c                   21.4071(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.236(4)
_cell_angle_gamma                90
_cell_volume                     2736.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2657
_cell_measurement_theta_min      3
_cell_measurement_theta_max      65

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .22
_exptl_crystal_size_mid          .17
_exptl_crystal_size_min          .15
_exptl_absorpt_coefficient_mu    2.461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.308
_exptl_absorpt_correction_T_max  0.550


_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            18543
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.164
_diffrn_reflns_theta_max         68.150
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             4835
_reflns_number_gt                2603
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?

_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)+(0.0314P)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     SHELXL
_refine_ls_extinction_coef       0.00072(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4835
_refine_ls_number_parameters     366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0663
_refine_ls_goodness_of_fit_ref   0.779
_refine_ls_restrained_S_all      0.779
_refine_ls_shift/su_max          0.001
_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
Cl1A Cl 0.48812(3) 0.75984(13) 0.12949(3) 0.0971(3) Uani 1 1 d . . . . .
O1A O 0.79043(8) 0.9472(2) 0.46618(6) 0.0649(5) Uani 1 1 d . . . . .
N1A N 0.61764(9) 0.8332(3) 0.19618(7) 0.0498(5) Uani 1 1 d . . . . .
N2A N 0.54824(13) 0.8052(4) -0.02652(10) 0.0857(7) Uani 1 1 d . . . . .
N3A N 0.76756(14) 0.9333(4) -0.00145(10) 0.0879(8) Uani 1 1 d . . . . .
C2A C 0.58353(12) 0.8157(3) 0.13818(10) 0.0535(6) Uani 1 1 d . . . . .
C3A C 0.61940(12) 0.8396(3) 0.08536(9) 0.0477(6) Uani 1 1 d . . . . .
C4A C 0.69686(12) 0.8840(3) 0.09566(9) 0.0443(5) Uani 1 1 d . . . . .
C5A C 0.73542(11) 0.9065(3) 0.15615(9) 0.0418(5) Uani 1 1 d . . . . .
C6A C 0.69212(11) 0.8765(3) 0.20625(9) 0.0403(5) Uani 1 1 d . . . . .
C7A C 0.57954(13) 0.8203(4) 0.02296(11) 0.0600(7) Uani 1 1 d . . . . .
C8A C 0.73681(13) 0.9110(3) 0.04169(11) 0.0576(6) Uani 1 1 d . . . . .
C9A C 0.81727(12) 0.9668(3) 0.16373(10) 0.0530(6) Uani 1 1 d . . . . .
H9A1 H 0.8498 0.8613 0.1642 0.079 Uiso 1 1 calc R U . . .
H9A2 H 0.8286 1.0328 0.2026 0.079 Uiso 1 1 calc R U . . .
H9A3 H 0.8258 1.0451 0.1292 0.079 Uiso 1 1 calc R U . . .
C10A C 0.72204(11) 0.8963(3) 0.27412(9) 0.0377(5) Uani 1 1 d . . . . .
C11A C 0.79600(11) 0.8470(3) 0.29847(10) 0.0451(5) Uani 1 1 d . . . . .
H11A H 0.8294 0.8044 0.2715 0.054 Uiso 1 1 calc R U . . .
C12A C 0.82071(11) 0.8606(3) 0.36256(10) 0.0473(6) Uani 1 1 d . . . . .
H12A H 0.8701 0.8259 0.3783 0.057 Uiso 1 1 calc R U . . .
C13A C 0.77216(12) 0.9250(3) 0.40243(9) 0.0449(5) Uani 1 1 d . . . . .
C14A C 0.69801(11) 0.9751(3) 0.37926(9) 0.0450(5) Uani 1 1 d . . . . .
H14A H 0.6650 1.0189 0.4064 0.054 Uiso 1 1 calc R U . . .
C15A C 0.67372(11) 0.9595(3) 0.31586(9) 0.0417(5) Uani 1 1 d . . . . .
H15A H 0.6239 0.9919 0.3006 0.050 Uiso 1 1 calc R U . . .
C16A C 0.86013(15) 0.8708(4) 0.49553(12) 0.0778(8) Uani 1 1 d . . . . .
H16A H 0.8601 0.7409 0.4885 0.117 Uiso 1 1 calc R U . . .
H16B H 0.8652 0.8948 0.5400 0.117 Uiso 1 1 calc R U . . .
H16C H 0.9022 0.9254 0.4779 0.117 Uiso 1 1 calc R U . . .
Cl1B Cl 0.18223(4) 0.61334(11) 0.07654(2) 0.0743(2) Uani 1 1 d . . . . .
O1B O 0.53656(7) 0.6988(2) 0.38238(6) 0.0590(4) Uani 1 1 d . . . . .
N1B N 0.23823(9) 0.6486(3) 0.19348(7) 0.0466(5) Uani 1 1 d . . . . .
N2B N -0.02074(12) 0.6770(4) 0.09690(11) 0.0850(7) Uani 1 1 d . . . . .
N3B N -0.02818(12) 0.7555(4) 0.27795(11) 0.0951(8) Uani 1 1 d . . . . .
C2B C 0.17401(12) 0.6498(3) 0.15508(9) 0.0481(6) Uani 1 1 d . . . . .
C3B C 0.10334(11) 0.6767(3) 0.17418(10) 0.0471(5) Uani 1 1 d . . . . .
C4B C 0.10239(11) 0.7093(3) 0.23839(10) 0.0461(5) Uani 1 1 d . . . . .
C5B C 0.16898(11) 0.7128(3) 0.28061(9) 0.0448(5) Uani 1 1 d . . . . .
C6B C 0.23742(11) 0.6780(3) 0.25580(9) 0.0414(5) Uani 1 1 d . . . . .
C7B C 0.03420(14) 0.6760(4) 0.13076(11) 0.0599(6) Uani 1 1 d . . . . .
C8B C 0.02941(14) 0.7375(4) 0.26059(11) 0.0619(7) Uani 1 1 d . . . . .
C9B C 0.16323(12) 0.7593(4) 0.34846(10) 0.0667(7) Uani 1 1 d . . . . .
H9B1 H 0.1184 0.8322 0.3509 0.100 Uiso 1 1 calc R U . . .
H9B2 H 0.2076 0.8271 0.3656 0.100 Uiso 1 1 calc R U . . .
H9B3 H 0.1600 0.6483 0.3721 0.100 Uiso 1 1 calc R U . . .
C10B C 0.31458(10) 0.6761(3) 0.29201(9) 0.0406(5) Uani 1 1 d . . . . .
C11B C 0.32929(11) 0.6309(3) 0.35551(9) 0.0480(6) Uani 1 1 d . . . . .
H11B H 0.2890 0.5968 0.3771 0.058 Uiso 1 1 calc R U . . .
C12B C 0.40221(11) 0.6355(3) 0.38714(9) 0.0503(6) Uani 1 1 d . . . . .
H12B H 0.4106 0.6056 0.4297 0.060 Uiso 1 1 calc R U . . .
C13B C 0.46272(11) 0.6844(3) 0.35588(9) 0.0440(5) Uani 1 1 d . . . . .
C14B C 0.44970(11) 0.7240(3) 0.29191(9) 0.0479(6) Uani 1 1 d . . . . .
H14B H 0.4904 0.7532 0.2701 0.057 Uiso 1 1 calc R U . . .
C15B C 0.37715(11) 0.7200(3) 0.26115(9) 0.0455(5) Uani 1 1 d . . . . .
H15B H 0.3692 0.7475 0.2184 0.055 Uiso 1 1 calc R U . . .
C16B C 0.55289(14) 0.6763(4) 0.44876(10) 0.0778(8) Uani 1 1 d . . . . .
H16D H 0.5217 0.7586 0.4695 0.117 Uiso 1 1 calc R U . . .
H16E H 0.6058 0.7028 0.4618 0.117 Uiso 1 1 calc R U . . .
H16F H 0.5422 0.5522 0.4598 0.117 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
Cl1A C2A 1.721(2) . ?
O1A C13A 1.372(2) . ?
O1A C16A 1.423(3) . ?
N1A C2A 1.316(3) . ?
N1A C6A 1.344(2) . ?
N2A C7A 1.137(3) . ?
N3A C8A 1.140(3) . ?
C2A C3A 1.375(3) . ?
C3A C4A 1.396(3) . ?
C3A C7A 1.436(3) . ?
C4A C5A 1.395(3) . ?
C4A C8A 1.441(3) . ?
C5A C6A 1.411(3) . ?
C5A C9A 1.500(3) . ?
C6A C10A 1.489(3) . ?
C10A C15A 1.390(3) . ?
C10A C11A 1.391(3) . ?
C11A C12A 1.390(3) . ?
C12A C13A 1.367(3) . ?
C13A C14A 1.390(3) . ?
C14A C15A 1.376(3) . ?
Cl1B C2B 1.726(2) . ?
O1B C13B 1.359(2) . ?
O1B C16B 1.423(3) . ?
N1B C2B 1.314(2) . ?
N1B C6B 1.353(2) . ?
N2B C7B 1.136(3) . ?
N3B C8B 1.134(3) . ?
C2B C3B 1.376(3) . ?
C3B C4B 1.397(3) . ?
C3B C7B 1.439(3) . ?
C4B C5B 1.390(3) . ?
C4B C8B 1.444(3) . ?
C5B C6B 1.404(3) . ?
C5B C9B 1.507(3) . ?
C6B C10B 1.481(3) . ?
C10B C11B 1.391(3) . ?
C10B C15B 1.395(3) . ?
C11B C12B 1.378(3) . ?
C12B C13B 1.377(3) . ?
C13B C14B 1.390(3) . ?
C14B C15B 1.365(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
C13A O1A C16A 118.37(17) . . ?
C2A N1A C6A 119.77(16) . . ?
N1A C2A C3A 124.06(19) . . ?
N1A C2A Cl1A 116.77(15) . . ?
C3A C2A Cl1A 119.17(16) . . ?
C2A C3A C4A 116.31(18) . . ?
C2A C3A C7A 122.0(2) . . ?
C4A C3A C7A 121.69(18) . . ?
C5A C4A C3A 121.88(17) . . ?
C5A C4A C8A 119.80(19) . . ?
C3A C4A C8A 118.30(18) . . ?
C4A C5A C6A 116.07(18) . . ?
C4A C5A C9A 119.09(17) . . ?
C6A C5A C9A 124.79(18) . . ?
N1A C6A C5A 121.89(17) . . ?
N1A C6A C10A 113.54(16) . . ?
C5A C6A C10A 124.53(18) . . ?
N2A C7A C3A 179.7(3) . . ?
N3A C8A C4A 179.1(3) . . ?
C15A C10A C11A 117.94(17) . . ?
C15A C10A C6A 119.22(17) . . ?
C11A C10A C6A 122.78(17) . . ?
C12A C11A C10A 120.98(19) . . ?
C13A C12A C11A 119.80(19) . . ?
C12A C13A O1A 125.04(19) . . ?
C12A C13A C14A 120.30(19) . . ?
O1A C13A C14A 114.66(18) . . ?
C15A C14A C13A 119.55(18) . . ?
C14A C15A C10A 121.42(19) . . ?
C13B O1B C16B 118.08(16) . . ?
C2B N1B C6B 120.01(16) . . ?
N1B C2B C3B 123.98(18) . . ?
N1B C2B Cl1B 115.87(15) . . ?
C3B C2B Cl1B 120.15(16) . . ?
C2B C3B C4B 116.14(17) . . ?
C2B C3B C7B 122.39(19) . . ?
C4B C3B C7B 121.46(18) . . ?
C5B C4B C3B 121.92(17) . . ?
C5B C4B C8B 120.04(19) . . ?
C3B C4B C8B 118.04(18) . . ?
C4B C5B C6B 116.68(17) . . ?
C4B C5B C9B 118.46(17) . . ?
C6B C5B C9B 124.83(18) . . ?
N1B C6B C5B 121.22(17) . . ?
N1B C6B C10B 113.03(15) . . ?
C5B C6B C10B 125.70(17) . . ?
N2B C7B C3B 179.2(3) . . ?
N3B C8B C4B 178.4(3) . . ?
C11B C10B C15B 117.12(18) . . ?
C11B C10B C6B 124.06(17) . . ?
C15B C10B C6B 118.82(17) . . ?
C12B C11B C10B 121.49(18) . . ?
C13B C12B C11B 120.13(19) . . ?
O1B C13B C12B 125.43(18) . . ?
O1B C13B C14B 115.20(17) . . ?
C12B C13B C14B 119.36(18) . . ?
C15B C14B C13B 119.96(18) . . ?
C14B C15B C10B 121.88(18) . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4

