# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_01
_database_code_depnum_ccdc_archive 'CCDC 1037307'
_audit_update_record             
;
2014-12-03 deposited with the CCDC.
2015-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 Cl N2 O2'
_chemical_formula_weight         336.76

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   'P2(1)/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                   6.021(2)
_cell_length_b                   16.358(6)
_cell_length_c                   16.457(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.874(4)
_cell_angle_gamma                90.00
_cell_volume                     1609.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9286
_exptl_absorpt_correction_T_max  0.9400
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9556
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2812
_reflns_number_gt                2045
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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)+(0.1000P)²+0.2967P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2812
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1676
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.09422(16) 1.01468(5) 0.31603(5) 0.0656(3) Uani 1 1 d . . .
O2 O 0.4976(3) 0.81888(12) 0.57291(12) 0.0511(5) Uani 1 1 d . . .
O1 O 0.4164(4) 0.56937(14) 0.57965(14) 0.0764(8) Uani 1 1 d . . .
N1 N 0.5264(4) 0.62524(12) 0.55163(12) 0.0389(6) Uani 1 1 d . . .
N2 N 0.4899(4) 0.66057(13) 0.48231(12) 0.0383(5) Uani 1 1 d . . .
C1 C 0.7275(5) 0.65237(15) 0.60228(14) 0.0359(6) Uani 1 1 d . . .
C2 C 0.8106(4) 0.73135(15) 0.59528(15) 0.0373(6) Uani 1 1 d . . .
C3 C 1.0125(5) 0.75040(17) 0.64074(18) 0.0519(8) Uani 1 1 d . . .
H3 H 1.0745 0.8020 0.6358 0.062 Uiso 1 1 calc R . .
C4 C 1.1238(6) 0.6937(2) 0.6936(2) 0.0636(9) Uani 1 1 d . . .
H4 H 1.2588 0.7074 0.7240 0.076 Uiso 1 1 calc R . .
C5 C 1.0339(6) 0.6170(2) 0.70089(19) 0.0613(9) Uani 1 1 d . . .
H5 H 1.1073 0.5793 0.7370 0.074 Uiso 1 1 calc R . .
C6 C 0.8368(5) 0.59576(17) 0.65518(16) 0.0486(7) Uani 1 1 d . . .
H6 H 0.7772 0.5437 0.6597 0.058 Uiso 1 1 calc R . .
C7 C 0.2963(5) 0.64122(15) 0.42785(15) 0.0373(6) Uani 1 1 d . . .
C8 C 0.1043(5) 0.59977(16) 0.44509(18) 0.0457(7) Uani 1 1 d . . .
H8 H 0.0964 0.5779 0.4968 0.055 Uiso 1 1 calc R . .
C9 C -0.0742(5) 0.59161(17) 0.3841(2) 0.0569(8) Uani 1 1 d . . .
H9 H -0.2032 0.5647 0.3953 0.068 Uiso 1 1 calc R . .
C10 C -0.0624(6) 0.6229(2) 0.3069(2) 0.0619(9) Uani 1 1 d . . .
H10 H -0.1831 0.6169 0.2664 0.074 Uiso 1 1 calc R . .
C11 C 0.1265(6) 0.6630(2) 0.28948(18) 0.0593(9) Uani 1 1 d . . .
H11 H 0.1345 0.6835 0.2372 0.071 Uiso 1 1 calc R . .
C12 C 0.3053(5) 0.67286(18) 0.35005(16) 0.0491(7) Uani 1 1 d . . .
H12 H 0.4321 0.7009 0.3385 0.059 Uiso 1 1 calc R . .
C13 C 0.6777(5) 0.79991(15) 0.55107(15) 0.0377(6) Uani 1 1 d . . .
C14 C 0.7803(4) 0.84866(14) 0.48867(15) 0.0346(6) Uani 1 1 d . . .
C15 C 0.6831(5) 0.92329(16) 0.46449(17) 0.0469(7) Uani 1 1 d . . .
H15 H 0.5521 0.9393 0.4848 0.056 Uiso 1 1 calc R . .
C16 C 0.7766(6) 0.97385(17) 0.41128(17) 0.0516(8) Uani 1 1 d . . .
H16 H 0.7107 1.0238 0.3961 0.062 Uiso 1 1 calc R . .
C17 C 0.9688(5) 0.94958(16) 0.38072(15) 0.0428(7) Uani 1 1 d . . .
C18 C 1.0648(5) 0.87479(16) 0.40085(18) 0.0497(7) Uani 1 1 d . . .
H18 H 1.1919 0.8581 0.3784 0.060 Uiso 1 1 calc R . .
C19 C 0.9690(5) 0.82469(16) 0.45509(18) 0.0479(7) Uani 1 1 d . . .
H19 H 1.0331 0.7741 0.4690 0.057 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
Cl1 C17 1.741(3) . ?
O2 C13 1.223(3) . ?
O1 N1 1.249(3) . ?
N1 N2 1.274(3) . ?
N1 C1 1.454(3) . ?
N2 C7 1.418(3) . ?
C1 C6 1.383(4) . ?
C1 C2 1.395(3) . ?
C2 C3 1.384(4) . ?
C2 C13 1.513(3) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.388(4) . ?
C7 C8 1.399(4) . ?
C8 C9 1.387(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.491(4) . ?
C14 C19 1.379(4) . ?
C14 C15 1.391(4) . ?
C15 C16 1.373(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(4) . ?
C18 C19 1.387(4) . ?
C18 H18 0.9300 . ?
C19 H19 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
O1 N1 N2 128.3(2) . . ?
O1 N1 C1 117.0(2) . . ?
N2 N1 C1 114.7(2) . . ?
N1 N2 C7 120.4(2) . . ?
C6 C1 C2 121.6(3) . . ?
C6 C1 N1 117.2(2) . . ?
C2 C1 N1 121.2(2) . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 C13 118.2(2) . . ?
C1 C2 C13 123.5(2) . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C12 C7 C8 119.5(3) . . ?
C12 C7 N2 112.3(2) . . ?
C8 C7 N2 128.1(2) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 120.5(3) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
O2 C13 C14 121.4(2) . . ?
O2 C13 C2 118.9(2) . . ?
C14 C13 C2 119.3(2) . . ?
C19 C14 C15 118.3(2) . . ?
C19 C14 C13 123.6(2) . . ?
C15 C14 C13 118.2(2) . . ?
C16 C15 C14 121.4(3) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 119.1(2) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 121.1(3) . . ?
C16 C17 Cl1 119.5(2) . . ?
C18 C17 Cl1 119.4(2) . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C14 C19 C18 121.1(2) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.073
