# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_mo_nj_djj_42_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Cl N3 O'
_chemical_formula_sum            'C16 H12 Cl N3 O'
_chemical_formula_weight         297.74

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   15.8817(11)
_cell_length_b                   5.8250(4)
_cell_length_c                   16.5782(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.321(2)
_cell_angle_gamma                90.00
_cell_volume                     1362.58(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9457
_exptl_absorpt_correction_T_max  0.9536
_exptl_absorpt_process_details   'SADABS(Bruker 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'Bruker D8 VENTURE PHOTON'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        NONE
_diffrn_reflns_number            12810
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.71
_reflns_number_total             2584
_reflns_number_gt                1914
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker D8 VENTURE'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0510P)^2^+0.3545P] where P=(Fo^2^+2Fc^2^)/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         2584
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.003
_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
Cl1 Cl 0.64189(4) 0.84110(10) 0.05201(3) 0.0650(2) Uani 1 1 d . . .
C13 C 0.66100(12) 0.8342(3) 0.22136(12) 0.0402(4) Uani 1 1 d . . .
H13 H 0.6893 0.9774 0.2278 0.048 Uiso 1 1 calc R . .
N3 N 0.62270(10) 0.5157(3) 0.43230(10) 0.0396(4) Uani 1 1 d . . .
N1 N 0.56712(11) 0.1723(3) 0.57229(10) 0.0420(4) Uani 1 1 d . . .
H1 H 0.5422 0.0542 0.5841 0.050 Uiso 1 1 calc R . .
O1 O 0.67836(11) 0.8620(2) 0.36915(9) 0.0549(4) Uani 1 1 d . . .
H1A H 0.6636 0.7943 0.4042 0.082 Uiso 1 1 calc R . .
N2 N 0.56279(11) 0.2114(3) 0.48999(10) 0.0431(4) Uani 1 1 d . . .
C9 C 0.61018(12) 0.4078(3) 0.50155(11) 0.0369(4) Uani 1 1 d . . .
C8 C 0.64354(12) 0.4917(3) 0.58949(12) 0.0387(4) Uani 1 1 d . . .
H8 H 0.6784 0.6251 0.6132 0.046 Uiso 1 1 calc R . .
C10 C 0.59891(13) 0.4131(3) 0.35655(12) 0.0402(4) Uani 1 1 d . . .
H10 H 0.5739 0.2657 0.3486 0.048 Uiso 1 1 calc R . .
C11 C 0.60975(11) 0.5191(3) 0.28323(11) 0.0352(4) Uani 1 1 d . . .
C6 C 0.62651(12) 0.3291(3) 0.72704(12) 0.0359(4) Uani 1 1 d . . .
C12 C 0.64994(12) 0.7393(3) 0.29242(12) 0.0370(4) Uani 1 1 d . . .
C16 C 0.58054(13) 0.4055(3) 0.20097(13) 0.0446(5) Uani 1 1 d . . .
H16 H 0.5537 0.2604 0.1940 0.054 Uiso 1 1 calc R . .
C3 C 0.64994(14) 0.3241(4) 0.90413(13) 0.0497(5) Uani 1 1 d . . .
H3 H 0.6574 0.3227 0.9632 0.060 Uiso 1 1 calc R . .
C7 C 0.61429(12) 0.3364(3) 0.63398(12) 0.0357(4) Uani 1 1 d . . .
C15 C 0.58990(13) 0.4996(3) 0.12972(12) 0.0456(5) Uani 1 1 d . . .
H15 H 0.5699 0.4207 0.0752 0.055 Uiso 1 1 calc R . .
C5 C 0.59476(14) 0.1463(3) 0.75890(13) 0.0459(5) Uani 1 1 d . . .
H5 H 0.5653 0.0227 0.7208 0.055 Uiso 1 1 calc R . .
C14 C 0.62989(13) 0.7151(3) 0.14136(12) 0.0420(5) Uani 1 1 d . . .
C4 C 0.60630(14) 0.1453(4) 0.84664(13) 0.0505(5) Uani 1 1 d . . .
H4 H 0.5841 0.0215 0.8669 0.061 Uiso 1 1 calc R . .
C2 C 0.68259(14) 0.5061(4) 0.87371(13) 0.0528(5) Uani 1 1 d . . .
H2 H 0.7128 0.6280 0.9125 0.063 Uiso 1 1 calc R . .
C1 C 0.67083(13) 0.5087(3) 0.78613(13) 0.0469(5) Uani 1 1 d . . .
H1B H 0.6930 0.6332 0.7663 0.056 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0841(4) 0.0757(4) 0.0434(3) 0.0119(3) 0.0364(3) -0.0082(3)
C13 0.0430(11) 0.0354(10) 0.0432(11) 0.0044(8) 0.0206(9) -0.0034(8)
N3 0.0414(9) 0.0425(9) 0.0380(8) 0.0054(7) 0.0209(7) -0.0011(7)
N1 0.0495(9) 0.0448(9) 0.0339(8) 0.0035(7) 0.0209(7) -0.0116(7)
O1 0.0815(10) 0.0462(8) 0.0444(8) -0.0085(7) 0.0353(8) -0.0185(7)
N2 0.0484(9) 0.0501(10) 0.0324(8) 0.0032(7) 0.0199(7) -0.0089(8)
C9 0.0351(10) 0.0407(11) 0.0375(10) 0.0071(8) 0.0189(8) 0.0006(8)
C8 0.0389(10) 0.0368(10) 0.0415(10) 0.0008(8) 0.0194(8) -0.0041(8)
C10 0.0408(10) 0.0370(10) 0.0456(11) 0.0052(9) 0.0223(9) -0.0013(8)
C11 0.0351(10) 0.0348(10) 0.0376(10) 0.0039(8) 0.0181(8) 0.0011(8)
C6 0.0311(9) 0.0411(11) 0.0353(9) 0.0033(8) 0.0151(7) 0.0019(8)
C12 0.0390(10) 0.0371(10) 0.0354(9) 0.0015(8) 0.0176(8) 0.0004(8)
C16 0.0479(11) 0.0391(11) 0.0469(11) -0.0021(9) 0.0218(9) -0.0056(9)
C3 0.0490(12) 0.0661(14) 0.0361(10) 0.0023(10) 0.0213(9) 0.0043(10)
C7 0.0325(9) 0.0381(10) 0.0356(9) 0.0022(8) 0.0149(8) 0.0001(8)
C15 0.0495(11) 0.0493(12) 0.0366(10) -0.0041(9) 0.0186(9) -0.0039(9)
C5 0.0507(12) 0.0455(12) 0.0390(10) -0.0002(9) 0.0184(9) -0.0105(9)
C14 0.0418(10) 0.0506(12) 0.0352(10) 0.0105(9) 0.0191(8) 0.0040(9)
C4 0.0554(12) 0.0555(13) 0.0415(11) 0.0095(10) 0.0232(10) -0.0062(10)
C2 0.0595(13) 0.0545(13) 0.0448(11) -0.0127(10) 0.0244(10) -0.0103(10)
C1 0.0517(12) 0.0448(11) 0.0479(11) -0.0026(10) 0.0260(9) -0.0086(9)

_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
Cl1 C14 1.7401(18) . ?
C13 C14 1.372(3) . ?
C13 C12 1.384(2) . ?
C13 H13 0.9300 . ?
N3 C10 1.281(2) . ?
N3 C9 1.401(2) . ?
N1 C7 1.348(2) . ?
N1 N2 1.3535(19) . ?
N1 H1 0.8600 . ?
O1 C12 1.344(2) . ?
O1 H1A 0.8200 . ?
N2 C9 1.334(2) . ?
C9 C8 1.391(2) . ?
C8 C7 1.376(2) . ?
C8 H8 0.9300 . ?
C10 C11 1.442(2) . ?
C10 H10 0.9300 . ?
C11 C16 1.390(2) . ?
C11 C12 1.409(3) . ?
C6 C5 1.383(2) . ?
C6 C1 1.385(3) . ?
C6 C7 1.465(2) . ?
C16 C15 1.371(3) . ?
C16 H16 0.9300 . ?
C3 C4 1.367(3) . ?
C3 C2 1.373(3) . ?
C3 H3 0.9300 . ?
C15 C14 1.380(3) . ?
C15 H15 0.9300 . ?
C5 C4 1.380(3) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C2 C1 1.376(3) . ?
C2 H2 0.9300 . ?
C1 H1B 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
C14 C13 C12 119.39(17) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C10 N3 C9 120.32(16) . . ?
C7 N1 N2 113.52(14) . . ?
C7 N1 H1 123.2 . . ?
N2 N1 H1 123.2 . . ?
C12 O1 H1A 109.5 . . ?
C9 N2 N1 103.59(14) . . ?
N2 C9 C8 111.74(15) . . ?
N2 C9 N3 123.38(16) . . ?
C8 C9 N3 124.87(16) . . ?
C7 C8 C9 105.71(16) . . ?
C7 C8 H8 127.1 . . ?
C9 C8 H8 127.1 . . ?
N3 C10 C11 122.06(17) . . ?
N3 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C16 C11 C12 118.03(16) . . ?
C16 C11 C10 120.52(16) . . ?
C12 C11 C10 121.45(16) . . ?
C5 C6 C1 117.89(17) . . ?
C5 C6 C7 121.99(17) . . ?
C1 C6 C7 120.12(16) . . ?
O1 C12 C13 118.33(16) . . ?
O1 C12 C11 121.68(16) . . ?
C13 C12 C11 119.99(16) . . ?
C15 C16 C11 122.39(18) . . ?
C15 C16 H16 118.8 . . ?
C11 C16 H16 118.8 . . ?
C4 C3 C2 119.22(18) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
N1 C7 C8 105.44(15) . . ?
N1 C7 C6 122.51(15) . . ?
C8 C7 C6 132.06(17) . . ?
C16 C15 C14 117.92(17) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C4 C5 C6 120.70(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C13 C14 C15 122.25(17) . . ?
C13 C14 Cl1 118.55(15) . . ?
C15 C14 Cl1 119.20(14) . . ?
C3 C4 C5 120.76(19) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C3 C2 C1 120.31(19) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C1 C6 121.11(19) . . ?
C2 C1 H1B 119.4 . . ?
C6 C1 H1B 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.71
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.037

_database_code_depnum_ccdc_archive 'CCDC 941059'