# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_msu009
_database_code_depnum_ccdc_archive 'CCDC 986336'
_audit_update_record             
;
2014-02-11 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 Cl N2 O2'
_chemical_formula_weight         298.72

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'
O O 0.0106 0.0060 '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'
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   'P 21/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                   5.0576(4)
_cell_length_b                   11.4615(7)
_cell_length_c                   23.3465(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.898(6)
_cell_angle_gamma                90.00
_cell_volume                     1352.60(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2361
_cell_measurement_theta_min      3.1589
_cell_measurement_theta_max      32.9983

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_min  0.9368
_exptl_absorpt_correction_T_max  0.9635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8228
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_sigmaI/netI    0.0543
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2368
_reflns_number_gt                1904
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0772P)²+1.5511P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2368
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1858
_refine_ls_wR_factor_gt          0.1740
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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
Cl1 Cl 0.80239(17) 0.48400(9) 0.25629(4) 0.0473(4) Uani 1 1 d . . .
N1 N 1.4468(5) 0.5704(3) 0.07919(12) 0.0418(7) Uani 1 1 d . . .
N2 N 1.0641(5) 0.4689(3) 0.13413(12) 0.0382(7) Uani 1 1 d . . .
H2 H 1.1321 0.4535 0.1008 0.046 Uiso 1 1 calc R . .
O1 O 0.4012(5) 0.3072(3) 0.25257(11) 0.0564(8) Uani 1 1 d . . .
O2 O 0.9095(5) 0.3207(3) 0.05589(11) 0.0553(8) Uani 1 1 d . . .
C1 C 1.6311(7) 0.6201(4) 0.04692(16) 0.0492(10) Uani 1 1 d . . .
H1 H 1.6758 0.5827 0.0122 0.059 Uiso 1 1 calc R . .
C2 C 1.7577(7) 0.7223(4) 0.06157(16) 0.0503(10) Uani 1 1 d . . .
H2A H 1.8887 0.7544 0.0379 0.060 Uiso 1 1 calc R . .
C3 C 1.6899(8) 0.7767(4) 0.11126(19) 0.0586(11) Uani 1 1 d . . .
H3 H 1.7744 0.8475 0.1225 0.070 Uiso 1 1 calc R . .
C4 C 1.4987(7) 0.7286(3) 0.14495(17) 0.0497(10) Uani 1 1 d . . .
H4 H 1.4472 0.7659 0.1792 0.060 Uiso 1 1 calc R . .
C5 C 1.3847(6) 0.6246(3) 0.12733(14) 0.0344(7) Uani 1 1 d . . .
C6 C 1.1830(6) 0.5670(3) 0.16451(15) 0.0375(8) Uani 1 1 d . . .
H6A H 1.2701 0.5397 0.2007 0.045 Uiso 1 1 calc R . .
H6B H 1.0445 0.6241 0.1742 0.045 Uiso 1 1 calc R . .
C7 C 0.8671(6) 0.3981(3) 0.14878(13) 0.0331(7) Uani 1 1 d . . .
C8 C 0.7332(6) 0.3917(3) 0.19878(13) 0.0341(7) Uani 1 1 d . . .
C9 C 0.5216(6) 0.3088(3) 0.20786(14) 0.0366(8) Uani 1 1 d . . .
C10 C 0.4531(6) 0.2247(3) 0.16092(15) 0.0381(8) Uani 1 1 d . . .
C11 C 0.2544(7) 0.1425(3) 0.16898(18) 0.0486(10) Uani 1 1 d . . .
H11 H 0.1618 0.1416 0.2037 0.058 Uiso 1 1 calc R . .
C12 C 0.1927(8) 0.0627(4) 0.1266(2) 0.0622(12) Uani 1 1 d . . .
H12 H 0.0606 0.0055 0.1326 0.075 Uiso 1 1 calc R . .
C13 C 0.3219(8) 0.0650(4) 0.0750(2) 0.0639(12) Uani 1 1 d . . .
H13 H 0.2764 0.0103 0.0458 0.077 Uiso 1 1 calc R . .
C14 C 0.5186(8) 0.1479(4) 0.06620(18) 0.0541(10) Uani 1 1 d . . .
H14 H 0.6074 0.1501 0.0310 0.065 Uiso 1 1 calc R . .
C15 C 0.5830(6) 0.2269(3) 0.10927(15) 0.0388(8) Uani 1 1 d . . .
C16 C 0.7935(6) 0.3145(3) 0.10038(14) 0.0365(8) Uani 1 1 d . . .


_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 C8 1.736(3) . ?
N1 C5 1.331(4) . ?
N1 C1 1.344(4) . ?
N2 C7 1.338(4) . ?
N2 C6 1.449(4) . ?
N2 H2 0.8800 . ?
O1 C9 1.226(4) . ?
O2 C16 1.212(4) . ?
C1 C2 1.373(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.382(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.513(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.371(4) . ?
C7 C16 1.518(5) . ?
C8 C9 1.452(5) . ?
C9 C10 1.492(5) . ?
C10 C15 1.392(5) . ?
C10 C11 1.395(5) . ?
C11 C12 1.376(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.483(5) . ?

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
C5 N1 C1 117.6(3) . . ?
C7 N2 C6 130.2(3) . . ?
C7 N2 H2 114.9 . . ?
C6 N2 H2 114.9 . . ?
N1 C1 C2 123.3(3) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
N1 C5 C4 123.1(3) . . ?
N1 C5 C6 117.6(3) . . ?
C4 C5 C6 119.2(3) . . ?
N2 C6 C5 109.5(3) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 130.0(3) . . ?
N2 C7 C16 111.0(3) . . ?
C8 C7 C16 118.9(3) . . ?
C7 C8 C9 123.2(3) . . ?
C7 C8 Cl1 122.2(3) . . ?
C9 C8 Cl1 114.6(2) . . ?
O1 C9 C8 121.6(3) . . ?
O1 C9 C10 120.4(3) . . ?
C8 C9 C10 118.0(3) . . ?
C15 C10 C11 119.5(3) . . ?
C15 C10 C9 121.3(3) . . ?
C11 C10 C9 119.2(3) . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 119.9(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.3(4) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 120.7(3) . . ?
C14 C15 C16 119.6(3) . . ?
C10 C15 C16 119.7(3) . . ?
O2 C16 C15 122.0(3) . . ?
O2 C16 C7 119.1(3) . . ?
C15 C16 C7 118.9(3) . . ?

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
C5 N1 C1 C2 0.6(6) . . . . ?
N1 C1 C2 C3 -0.8(6) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C2 C3 C4 C5 1.1(7) . . . . ?
C1 N1 C5 C4 0.5(5) . . . . ?
C1 N1 C5 C6 -178.3(3) . . . . ?
C3 C4 C5 N1 -1.4(6) . . . . ?
C3 C4 C5 C6 177.5(4) . . . . ?
C7 N2 C6 C5 -175.4(3) . . . . ?
N1 C5 C6 N2 -9.1(4) . . . . ?
C4 C5 C6 N2 172.0(3) . . . . ?
C6 N2 C7 C8 -5.6(6) . . . . ?
C6 N2 C7 C16 174.6(3) . . . . ?
N2 C7 C8 C9 179.9(3) . . . . ?
C16 C7 C8 C9 -0.4(5) . . . . ?
N2 C7 C8 Cl1 0.6(5) . . . . ?
C16 C7 C8 Cl1 -179.7(2) . . . . ?
C7 C8 C9 O1 -178.2(3) . . . . ?
Cl1 C8 C9 O1 1.2(4) . . . . ?
C7 C8 C9 C10 1.8(5) . . . . ?
Cl1 C8 C9 C10 -178.8(2) . . . . ?
O1 C9 C10 C15 178.4(3) . . . . ?
C8 C9 C10 C15 -1.6(5) . . . . ?
O1 C9 C10 C11 -1.4(5) . . . . ?
C8 C9 C10 C11 178.6(3) . . . . ?
C15 C10 C11 C12 1.6(5) . . . . ?
C9 C10 C11 C12 -178.7(3) . . . . ?
C10 C11 C12 C13 -1.7(6) . . . . ?
C11 C12 C13 C14 0.8(7) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
C13 C14 C15 C10 -0.3(6) . . . . ?
C13 C14 C15 C16 179.5(4) . . . . ?
C11 C10 C15 C14 -0.6(5) . . . . ?
C9 C10 C15 C14 179.6(3) . . . . ?
C11 C10 C15 C16 179.7(3) . . . . ?
C9 C10 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 O2 1.2(5) . . . . ?
C10 C15 C16 O2 -179.0(3) . . . . ?
C14 C15 C16 C7 -178.2(3) . . . . ?
C10 C15 C16 C7 1.5(5) . . . . ?
N2 C7 C16 O2 -1.0(4) . . . . ?
C8 C7 C16 O2 179.2(3) . . . . ?
N2 C7 C16 C15 178.4(3) . . . . ?
C8 C7 C16 C15 -1.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_msu003
_database_code_depnum_ccdc_archive 'CCDC 986337'
_audit_update_record             
;
2014-02-11 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 Cl N O2'
_chemical_formula_weight         297.73

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'
O O 0.0106 0.0060 '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'
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   'P 21/c'

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                   10.2681(4)
_cell_length_b                   7.7447(3)
_cell_length_c                   17.5818(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.836(4)
_cell_angle_gamma                90.00
_cell_volume                     1395.03(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3512
_cell_measurement_theta_min      2.9477
_cell_measurement_theta_max      32.5263

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_min  0.9166
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10267
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2451
_reflns_number_gt                1919
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0572P)²+0.1841P] 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         2451
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 1.20249(6) 0.01137(8) 0.74522(4) 0.0657(3) Uani 1 1 d . . .
N1 N 1.10534(18) -0.3601(3) 0.67883(11) 0.0473(5) Uani 1 1 d . . .
O1 O 0.91710(17) -0.3844(2) 0.57403(10) 0.0673(5) Uani 1 1 d . . .
O2 O 1.04969(16) 0.2552(2) 0.65823(10) 0.0611(5) Uani 1 1 d . . .
C1 C 0.9432(2) -0.2384(3) 0.59417(12) 0.0427(5) Uani 1 1 d . . .
C2 C 0.87091(19) -0.0893(3) 0.56124(11) 0.0395(5) Uani 1 1 d . . .
C3 C 0.7677(2) -0.1168(3) 0.50668(12) 0.0493(6) Uani 1 1 d . . .
H3 H 0.7443 -0.2285 0.4919 0.059 Uiso 1 1 calc R . .
C4 C 0.7007(2) 0.0226(3) 0.47504(14) 0.0565(6) Uani 1 1 d . . .
H4 H 0.6318 0.0047 0.4388 0.068 Uiso 1 1 calc R . .
C5 C 0.7350(2) 0.1879(3) 0.49652(13) 0.0564(6) Uani 1 1 d . . .
H5 H 0.6890 0.2813 0.4750 0.068 Uiso 1 1 calc R . .
C6 C 0.8384(2) 0.2160(3) 0.55043(13) 0.0510(6) Uani 1 1 d . . .
H6 H 0.8619 0.3280 0.5646 0.061 Uiso 1 1 calc R . .
C7 C 0.90580(19) 0.0774(3) 0.58279(12) 0.0399(5) Uani 1 1 d . . .
C8 C 1.0170(2) 0.1071(3) 0.64113(12) 0.0428(5) Uani 1 1 d . . .
C9 C 1.08143(19) -0.0418(3) 0.67582(13) 0.0438(5) Uani 1 1 d . . .
C10 C 1.05316(18) -0.2088(3) 0.65495(12) 0.0392(5) Uani 1 1 d . . .
C11 C 1.2195(2) -0.4007(3) 0.73041(12) 0.0488(6) Uani 1 1 d . . .
H11A H 1.2037 -0.5079 0.7568 0.059 Uiso 1 1 calc R . .
H11B H 1.2311 -0.3102 0.7684 0.059 Uiso 1 1 calc R . .
C12 C 1.34369(19) -0.4182(3) 0.68884(11) 0.0424(5) Uani 1 1 d . . .
C13 C 1.4371(2) -0.2899(3) 0.69116(13) 0.0530(6) Uani 1 1 d . . .
H13 H 1.4254 -0.1906 0.7197 0.064 Uiso 1 1 calc R . .
C14 C 1.5479(2) -0.3081(4) 0.65134(14) 0.0606(7) Uani 1 1 d . . .
H14 H 1.6102 -0.2208 0.6531 0.073 Uiso 1 1 calc R . .
C15 C 1.5666(2) -0.4539(4) 0.60937(14) 0.0585(7) Uani 1 1 d . . .
H15 H 1.6410 -0.4651 0.5823 0.070 Uiso 1 1 calc R . .
C16 C 1.4753(2) -0.5832(4) 0.60738(14) 0.0623(7) Uani 1 1 d . . .
H16 H 1.4879 -0.6828 0.5793 0.075 Uiso 1 1 calc R . .
C17 C 1.3642(2) -0.5652(3) 0.64726(13) 0.0538(6) Uani 1 1 d . . .
H17 H 1.3027 -0.6535 0.6459 0.065 Uiso 1 1 calc R . .
H1N H 1.072(3) -0.450(4) 0.6561(15) 0.076(9) Uiso 1 1 d . . .


_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 C9 1.732(2) . ?
N1 C10 1.344(3) . ?
N1 C11 1.467(3) . ?
N1 H1N 0.86(3) . ?
O1 C1 1.210(3) . ?
O2 C8 1.227(3) . ?
C1 C2 1.471(3) . ?
C1 C10 1.519(3) . ?
C2 C7 1.385(3) . ?
C2 C3 1.398(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.501(3) . ?
C8 C9 1.444(3) . ?
C9 C10 1.370(3) . ?
C11 C12 1.518(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.377(3) . ?
C12 C13 1.380(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9300 . ?
C17 H17 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
C10 N1 C11 131.7(2) . . ?
C10 N1 H1N 114.9(19) . . ?
C11 N1 H1N 113.0(19) . . ?
O1 C1 C2 121.5(2) . . ?
O1 C1 C10 119.1(2) . . ?
C2 C1 C10 119.38(18) . . ?
C7 C2 C3 120.0(2) . . ?
C7 C2 C1 120.62(19) . . ?
C3 C2 C1 119.3(2) . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C2 119.9(2) . . ?
C6 C7 C8 120.0(2) . . ?
C2 C7 C8 120.06(19) . . ?
O2 C8 C9 122.2(2) . . ?
O2 C8 C7 119.6(2) . . ?
C9 C8 C7 118.16(18) . . ?
C10 C9 C8 123.9(2) . . ?
C10 C9 Cl1 122.83(18) . . ?
C8 C9 Cl1 113.22(16) . . ?
N1 C10 C9 131.8(2) . . ?
N1 C10 C1 110.52(18) . . ?
C9 C10 C1 117.69(19) . . ?
N1 C11 C12 112.56(17) . . ?
N1 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C17 C12 C13 118.7(2) . . ?
C17 C12 C11 119.5(2) . . ?
C13 C12 C11 121.8(2) . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 120.8(2) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?

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
O1 C1 C2 C7 -177.3(2) . . . . ?
C10 C1 C2 C7 2.8(3) . . . . ?
O1 C1 C2 C3 1.5(3) . . . . ?
C10 C1 C2 C3 -178.42(17) . . . . ?
C7 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C4 -179.2(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C5 C6 C7 C2 0.4(3) . . . . ?
C5 C6 C7 C8 -179.79(19) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C1 C2 C7 C6 178.92(19) . . . . ?
C3 C2 C7 C8 -179.74(18) . . . . ?
C1 C2 C7 C8 -0.9(3) . . . . ?
C6 C7 C8 O2 -2.0(3) . . . . ?
C2 C7 C8 O2 177.88(19) . . . . ?
C6 C7 C8 C9 177.49(19) . . . . ?
C2 C7 C8 C9 -2.6(3) . . . . ?
O2 C8 C9 C10 -175.8(2) . . . . ?
C7 C8 C9 C10 4.7(3) . . . . ?
O2 C8 C9 Cl1 2.4(3) . . . . ?
C7 C8 C9 Cl1 -177.08(14) . . . . ?
C11 N1 C10 C9 -6.8(4) . . . . ?
C11 N1 C10 C1 173.5(2) . . . . ?
C8 C9 C10 N1 177.5(2) . . . . ?
Cl1 C9 C10 N1 -0.6(3) . . . . ?
C8 C9 C10 C1 -2.9(3) . . . . ?
Cl1 C9 C10 C1 179.07(14) . . . . ?
O1 C1 C10 N1 -1.1(3) . . . . ?
C2 C1 C10 N1 178.82(17) . . . . ?
O1 C1 C10 C9 179.2(2) . . . . ?
C2 C1 C10 C9 -0.9(3) . . . . ?
C10 N1 C11 C12 -90.2(3) . . . . ?
N1 C11 C12 C17 -75.9(3) . . . . ?
N1 C11 C12 C13 103.8(2) . . . . ?
C17 C12 C13 C14 1.1(3) . . . . ?
C11 C12 C13 C14 -178.6(2) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C13 C12 C17 C16 -1.1(3) . . . . ?
C11 C12 C17 C16 178.6(2) . . . . ?
C15 C16 C17 C12 0.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_vks4
_database_code_depnum_ccdc_archive 'CCDC 986338'
_audit_update_record             
;
2014-02-11 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_audit_creation_date             2014-02-04
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_formula_moiety         'C17 H13 N O2'
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.30
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'C16 H12 N2 O2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z+1/2
3 -x+1/2,y+1/2,z+1/2
4 x+1/2,-y+1/2,z

_cell_length_a                   10.8597(13)
_cell_length_b                   24.115(4)
_cell_length_c                   5.0303(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1317.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    632
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.2453
_cell_measurement_theta_min      3.3725
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'reddish red'
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.3275
_exptl_crystal_description       needle
_exptl_crystal_F_000             552.2713
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0813
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3769
_diffrn_reflns_theta_full        27.9190
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         3.38
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 16.0938
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9990
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   13.00   61.00   1.0000    7.2500
omega____ theta____ kappa____ phi______ frames
    -       19.7923 -104.0000  133.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   58.00   1.0000    7.2500
omega____ theta____ kappa____ phi______ frames
    -       19.7923    0.0000  -30.0000 107
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0001206000
_diffrn_orient_matrix_UB_12      -0.0282465000
_diffrn_orient_matrix_UB_13      -0.0389324000
_diffrn_orient_matrix_UB_21      -0.0641399000
_diffrn_orient_matrix_UB_22      0.0016921000
_diffrn_orient_matrix_UB_23      -0.0261240000
_diffrn_orient_matrix_UB_31      0.0126727000
_diffrn_orient_matrix_UB_32      0.0079064000
_diffrn_orient_matrix_UB_33      -0.1329962000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.273
_reflns_limit_h_max              13
_reflns_limit_h_min              -12
_reflns_limit_k_max              30
_reflns_limit_k_min              -29
_reflns_limit_l_max              3
_reflns_limit_l_min              -6
_reflns_number_gt                1366
_reflns_number_total             1366
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.2752
_refine_diff_density_min         -0.3278
_refine_diff_density_rms         0.0700
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -3(4)
_refine_ls_d_res_high            0.7590
_refine_ls_d_res_low             6.0287
_refine_ls_goodness_of_fit_ref   1.1178
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0718
_refine_ls_restrained_S_all      1.1178
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+0.5958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1410
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C8(H8), C6(H6), C13(H13), C14(H14), C7(H7), C16(H16),
 C17(H17), C15(H15)
;
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_refinement_flags_posn
O1 O 0.5678(3) 0.32583(16) 0.2556(8) 0.0588(11) Uani 1.000000 .
O2 O 0.1530(4) 0.28396(19) 0.7891(8) 0.0722(14) Uani 1.000000 .
C4 C 0.3242(5) 0.3436(2) 0.7350(10) 0.0446(14) Uani 1.000000 .
C10 C 0.4745(5) 0.3171(2) 0.3838(10) 0.0420(14) Uani 1.000000 .
C1 C 0.3966(5) 0.2678(2) 0.3203(10) 0.0393(13) Uani 1.000000 .
N1 N 0.4396(4) 0.23629(18) 0.1223(8) 0.0496(12) Uani 1.000000 .
H1 H 0.5087(4) 0.24549(18) 0.0512(8) 0.0595(15) Uiso 1.000000 R
C9 C 0.4335(5) 0.3540(2) 0.6000(10) 0.0467(14) Uani 1.000000 .
C2 C 0.2914(5) 0.2580(3) 0.4589(10) 0.0461(15) Uani 1.000000 .
H2 H 0.2449(5) 0.2268(3) 0.4170(10) 0.0553(19) Uiso 1.000000 R
C3 C 0.2497(5) 0.2935(3) 0.6651(11) 0.0499(15) Uani 1.000000 .
C5 C 0.2858(7) 0.3790(3) 0.9357(12) 0.0671(19) Uani 1.000000 .
H5 H 0.2123(7) 0.3724(3) 1.0254(12) 0.080(2) Uiso 1.000000 R
C8 C 0.5039(6) 0.3998(2) 0.6663(11) 0.0616(18) Uani 1.000000 .
H8 H 0.5764(6) 0.4071(2) 0.5744(11) 0.074(2) Uiso 1.000000 R
C11 C 0.3777(5) 0.1880(2) 0.0206(12) 0.0545(16) Uani 1.000000 .
H11a H 0.2908(5) 0.1966(2) 0.0032(12) 0.0654(19) Uiso 1.000000 R
H11b H 0.4090(5) 0.1805(2) -0.1564(12) 0.0654(19) Uiso 1.000000 R
C12 C 0.3898(5) 0.1360(2) 0.1831(11) 0.0437(14) Uani 1.000000 .
C6 C 0.3580(9) 0.4242(3) 1.0007(13) 0.080(2) Uani 1.000000 .
H6 H 0.3329(9) 0.4479(3) 1.1358(13) 0.096(3) Uiso 1.000000 R
C13 C 0.4822(6) 0.1283(2) 0.3718(11) 0.0559(17) Uani 1.000000 .
H13 H 0.5386(6) 0.1564(2) 0.4053(11) 0.067(2) Uiso 1.000000 R
C14 C 0.4896(7) 0.0795(3) 0.5070(12) 0.068(2) Uani 1.000000 .
H14 H 0.5519(7) 0.0748(3) 0.6318(12) 0.082(2) Uiso 1.000000 R
C7 C 0.4665(8) 0.4346(3) 0.8690(13) 0.079(2) Uani 1.000000 .
H7 H 0.5145(8) 0.4650(3) 0.9161(13) 0.095(3) Uiso 1.000000 R
C16 C 0.3182(6) 0.0445(3) 0.2746(15) 0.075(2) Uani 1.000000 .
H16 H 0.2640(6) 0.0157(3) 0.2370(15) 0.090(3) Uiso 1.000000 R
C17 C 0.3084(6) 0.0938(3) 0.1423(13) 0.0653(18) Uani 1.000000 .
H17 H 0.2445(6) 0.0987(3) 0.0212(13) 0.078(2) Uiso 1.000000 R
C15 C 0.4089(7) 0.0376(3) 0.4647(14) 0.074(2) Uani 1.000000 .
H15 H 0.4144(7) 0.0048(3) 0.5616(14) 0.089(2) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C10 1.219(6) .
O2 C3 1.243(6) .
C4 C9 1.390(7) .
C4 C3 1.496(8) .
C4 C5 1.387(8) .
C10 C1 1.496(7) .
C10 C9 1.473(7) .
C1 N1 1.337(6) .
C1 C2 1.359(7) .
N1 C11 1.439(6) .
C9 C8 1.384(7) .
C2 C3 1.419(8) .
C5 C6 1.382(10) .
C8 C7 1.382(8) .
C11 C12 1.503(8) .
C12 C13 1.393(7) .
C12 C17 1.364(7) .
C6 C7 1.374(10) .
C13 C14 1.362(8) .
C14 C15 1.354(9) .
C16 C17 1.367(8) .
C16 C15 1.383(9) .

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
C3 C4 C9 119.5(5) . .
C5 C4 C9 120.0(6) . .
C5 C4 C3 120.4(6) . .
C1 C10 O1 119.6(5) . .
C9 C10 O1 122.6(5) . .
C9 C10 C1 117.8(5) . .
N1 C1 C10 114.4(4) . .
C2 C1 C10 120.3(5) . .
C2 C1 N1 125.3(5) . .
C11 N1 C1 124.1(5) . .
C10 C9 C4 120.6(5) . .
C8 C9 C4 119.9(5) . .
C8 C9 C10 119.5(5) . .
C3 C2 C1 122.6(5) . .
C4 C3 O2 119.2(5) . .
C2 C3 O2 121.7(6) . .
C2 C3 C4 119.1(5) . .
C6 C5 C4 119.1(7) . .
C7 C8 C9 120.0(7) . .
C12 C11 N1 116.2(5) . .
C13 C12 C11 123.0(5) . .
C17 C12 C11 118.9(5) . .
C17 C12 C13 118.1(5) . .
C7 C6 C5 121.1(7) . .
C14 C13 C12 119.8(6) . .
C15 C14 C13 121.9(6) . .
C6 C7 C8 119.8(7) . .
C15 C16 C17 119.8(7) . .
C16 C17 C12 121.7(6) . .
C16 C15 C14 118.7(6) . .


####################################################################### 
# 
# 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_msu002
_database_code_depnum_ccdc_archive 'CCDC 986339'
_audit_update_record             
;
2014-02-11 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_audit_creation_date             2014-02-04
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_formula_moiety         'C16 H16 Cl N O2'
_chemical_formula_sum            'C16 H16 Cl N O2'
_chemical_formula_weight         289.76
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.1167(10)
_cell_length_b                   8.3589(10)
_cell_length_c                   10.5321(13)
_cell_angle_alpha                92.178(10)
_cell_angle_beta                 104.565(11)
_cell_angle_gamma                94.094(10)
_cell_volume                     688.68(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293
_exptl_absorpt_coefficient_mu    0.278
_exptl_crystal_colour            reddish
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_density_diffrn    1.3972
_exptl_crystal_description       needle
_exptl_crystal_F_000             304.4287
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5755
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.07
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9979
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1846
_reflns_number_total             2429
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.3791
_refine_diff_density_min         -0.3873
_refine_diff_density_rms         0.0771
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             6.6341
_refine_ls_goodness_of_fit_ref   1.0392
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      1.0392
_refine_ls_shift/su_max          0.0020
_refine_ls_shift/su_mean         0.0006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1133P)²+0.0087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1872
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C13(H13a,H13b), C14(H14a,H14b), C15(H15a,H15b), C16(H16a,H16b)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10)
;
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_refinement_flags_posn
Cl1 Cl 0.10426(9) 0.91944(9) 0.70764(7) 0.0700(3) Uani 1.000000 .
O1 O 0.3450(3) 0.5990(3) 0.3854(2) 0.0737(6) Uani 1.000000 .
O2 O -0.2008(3) 0.7922(3) 0.5233(2) 0.0767(7) Uani 1.000000 .
N1 N 0.4062(3) 0.7663(3) 0.6061(2) 0.0621(6) Uani 1.000000 .
H1 H 0.4740(3) 0.7208(3) 0.5678(2) 0.0745(8) Uiso 1.000000 R
C1 C 0.2194(3) 0.6438(3) 0.4137(3) 0.0551(7) Uani 1.000000 .
C2 C 0.2414(3) 0.7452(3) 0.5408(2) 0.0516(6) Uani 1.000000 .
C3 C 0.0973(3) 0.7954(3) 0.5699(2) 0.0538(7) Uani 1.000000 .
C4 C -0.0746(3) 0.7517(3) 0.4911(3) 0.0557(7) Uani 1.000000 .
C5 C -0.0964(3) 0.6518(3) 0.3659(3) 0.0538(7) Uani 1.000000 .
C6 C 0.0460(3) 0.6041(3) 0.3281(3) 0.0535(6) Uani 1.000000 .
C7 C 0.0240(4) 0.5143(3) 0.2102(3) 0.0640(7) Uani 1.000000 .
H7 H 0.1185(4) 0.4816(3) 0.1845(3) 0.0769(9) Uiso 1.000000 R
C8 C -0.1391(4) 0.4737(4) 0.1310(3) 0.0722(9) Uani 1.000000 .
H8 H -0.1538(4) 0.4148(4) 0.0517(3) 0.0866(10) Uiso 1.000000 R
C9 C -0.2787(4) 0.5203(4) 0.1694(3) 0.0726(9) Uani 1.000000 .
H9 H -0.3877(4) 0.4924(4) 0.1159(3) 0.0872(10) Uiso 1.000000 R
C10 C -0.2589(4) 0.6088(4) 0.2876(3) 0.0652(8) Uani 1.000000 .
H10 H -0.3541(4) 0.6388(4) 0.3137(3) 0.0782(9) Uiso 1.000000 R
C11 C 0.4913(3) 0.8533(3) 0.7312(3) 0.0562(7) Uani 1.000000 .
H11 H 0.4137(3) 0.8483(3) 0.7890(3) 0.0674(8) Uiso 1.000000 R
C12 C 0.5351(4) 1.0283(3) 0.7101(3) 0.0671(8) Uani 1.000000 .
H12a H 0.6096(4) 1.0352(3) 0.6512(3) 0.0805(9) Uiso 1.000000 R
H12b H 0.4316(4) 1.0779(3) 0.6701(3) 0.0805(9) Uiso 1.000000 R
C13 C 0.6241(4) 1.1174(4) 0.8417(3) 0.0723(8) Uani 1.000000 .
H13a H 0.6553(4) 1.2281(4) 0.8271(3) 0.0868(10) Uiso 1.000000 R
H13b H 0.5459(4) 1.1176(4) 0.8978(3) 0.0868(10) Uiso 1.000000 R
C14 C 0.7830(4) 1.0392(4) 0.9099(3) 0.0764(9) Uani 1.000000 .
H14a H 0.8668(4) 1.0507(4) 0.8588(3) 0.0917(11) Uiso 1.000000 R
H14b H 0.8320(4) 1.0935(4) 0.9956(3) 0.0917(11) Uiso 1.000000 R
C15 C 0.7427(4) 0.8626(4) 0.9262(3) 0.0727(8) Uani 1.000000 .
H15a H 0.8480(4) 0.8143(4) 0.9634(3) 0.0873(10) Uiso 1.000000 R
H15b H 0.6711(4) 0.8519(4) 0.9871(3) 0.0873(10) Uiso 1.000000 R
C16 C 0.6516(3) 0.7736(4) 0.7960(3) 0.0617(7) Uani 1.000000 .
H16a H 0.6210(3) 0.6629(4) 0.8109(3) 0.0741(9) Uiso 1.000000 R
H16b H 0.7276(3) 0.7736(4) 0.7381(3) 0.0741(9) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C3 1.738(2) .
O1 C1 1.211(3) .
O2 C4 1.223(3) .
N1 H1 0.8600 .
N1 C2 1.337(3) .
N1 C11 1.463(3) .
C1 C2 1.522(3) .
C1 C6 1.475(4) .
C2 C3 1.370(4) .
C3 C4 1.446(4) .
C4 C5 1.499(4) .
C5 C6 1.392(4) .
C5 C10 1.383(4) .
C6 C7 1.392(4) .
C7 H7 0.9300 .
C7 C8 1.386(4) .
C8 H8 0.9300 .
C8 C9 1.372(5) .
C9 H9 0.9300 .
C9 C10 1.391(4) .
C10 H10 0.9300 .
C11 H11 0.9800 .
C11 C12 1.519(4) .
C11 C16 1.521(4) .
C12 H12a 0.9700 .
C12 H12b 0.9700 .
C12 C13 1.529(4) .
C13 H13a 0.9700 .
C13 H13b 0.9700 .
C13 C14 1.515(5) .
C14 H14a 0.9700 .
C14 H14b 0.9700 .
C14 C15 1.515(5) .
C15 H15a 0.9700 .
C15 H15b 0.9700 .
C15 C16 1.522(4) .
C16 H16a 0.9700 .
C16 H16b 0.9700 .

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
C2 N1 H1 114.38(14) . .
C11 N1 H1 114.38(14) . .
C11 N1 C2 131.2(2) . .
C2 C1 O1 119.0(2) . .
C6 C1 O1 122.0(2) . .
C6 C1 C2 119.1(2) . .
C1 C2 N1 110.5(2) . .
C3 C2 N1 131.7(2) . .
C3 C2 C1 117.7(2) . .
C2 C3 Cl1 122.7(2) . .
C4 C3 Cl1 113.02(19) . .
C4 C3 C2 124.3(2) . .
C3 C4 O2 122.6(3) . .
C5 C4 O2 119.5(2) . .
C5 C4 C3 117.9(2) . .
C6 C5 C4 120.2(2) . .
C10 C5 C4 119.5(2) . .
C10 C5 C6 120.3(3) . .
C5 C6 C1 120.6(2) . .
C7 C6 C1 119.8(2) . .
C7 C6 C5 119.6(3) . .
H7 C7 C6 120.07(17) . .
C8 C7 C6 119.9(3) . .
C8 C7 H7 120.07(19) . .
H8 C8 C7 119.93(19) . .
C9 C8 C7 120.1(3) . .
C9 C8 H8 119.93(17) . .
H9 C9 C8 119.66(17) . .
C10 C9 C8 120.7(3) . .
C10 C9 H9 119.66(18) . .
C9 C10 C5 119.4(3) . .
H10 C10 C5 120.31(17) . .
H10 C10 C9 120.31(18) . .
H11 C11 N1 108.69(14) . .
C12 C11 N1 110.6(2) . .
C12 C11 H11 108.69(15) . .
C16 C11 N1 109.5(2) . .
C16 C11 H11 108.69(15) . .
C16 C11 C12 110.7(2) . .
H12a C12 C11 109.69(15) . .
H12b C12 C11 109.69(15) . .
H12b C12 H12a 108.2 . .
C13 C12 C11 109.9(2) . .
C13 C12 H12a 109.69(18) . .
C13 C12 H12b 109.69(17) . .
H13a C13 C12 109.38(17) . .
H13b C13 C12 109.38(18) . .
H13b C13 H13a 108.0 . .
C14 C13 C12 111.2(3) . .
C14 C13 H13a 109.38(19) . .
C14 C13 H13b 109.38(19) . .
H14a C14 C13 109.36(19) . .
H14b C14 C13 109.36(16) . .
H14b C14 H14a 108.0 . .
C15 C14 C13 111.3(3) . .
C15 C14 H14a 109.36(17) . .
C15 C14 H14b 109.36(16) . .
H15a C15 C14 109.25(17) . .
H15b C15 C14 109.25(17) . .
H15b C15 H15a 107.9 . .
C16 C15 C14 111.8(2) . .
C16 C15 H15a 109.25(16) . .
C16 C15 H15b 109.25(17) . .
C15 C16 C11 110.4(2) . .
H16a C16 C11 109.57(15) . .
H16a C16 C15 109.57(17) . .
H16b C16 C11 109.57(15) . .
H16b C16 C15 109.57(16) . .
H16b C16 H16a 108.1 . .


####################################################################### 
# 
# 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_msu005
_database_code_depnum_ccdc_archive 'CCDC 986340'
_audit_update_record             
;
2014-02-11 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_audit_creation_date             2014-02-04
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_formula_moiety         'C15 H10 Cl N O3'
_chemical_formula_sum            'C15 H10 Cl N O3'
_chemical_formula_weight         287.70
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_cell_length_a                   7.4914(2)
_cell_length_b                   20.7986(5)
_cell_length_c                   7.9056(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.019(2)
_cell_angle_gamma                90
_cell_volume                     1230.07(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_exptl_absorpt_coefficient_mu    0.317
_exptl_crystal_colour            reddish
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_density_diffrn    1.5534
_exptl_crystal_description       plate
_exptl_crystal_F_000             592.8919
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13347
_diffrn_reflns_theta_full        24.9969
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.24
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                2071
_reflns_number_total             2164
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.2974
_refine_diff_density_min         -0.2324
_refine_diff_density_rms         0.0462
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             6.2880
_refine_ls_goodness_of_fit_ref   1.0546
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    19
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.0546
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+0.8927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0725
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15)
;
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_refinement_flags_posn
Cl1 Cl 0.69916(5) 0.295220(18) 1.18552(5) 0.02735(13) Uani 1.000000 .
O1 O 0.92129(15) 0.52266(5) 1.30496(14) 0.0254(3) Uani 1.000000 .
O2 O 0.63538(16) 0.35416(6) 0.86066(14) 0.0296(3) Uani 1.000000 .
O3 O 1.20558(14) 0.34313(5) 1.58327(14) 0.0247(3) Uani 1.000000 .
N1 N 0.86689(17) 0.40792(6) 1.42110(15) 0.0195(3) Uani 1.000000 .
H1 H 0.89333(17) 0.44259(6) 1.47615(15) 0.0234(3) Uiso 1.000000 R
C1 C 0.69083(19) 0.39362(7) 0.96644(18) 0.0197(3) Uani 1.000000 .
C2 C 0.74273(19) 0.37500(7) 1.13935(19) 0.0182(3) Uani 1.000000 .
C3 C 0.81507(18) 0.41689(7) 1.25786(18) 0.0159(3) Uani 1.000000 .
C4 C 0.84404(19) 0.48615(7) 1.20499(18) 0.0175(3) Uani 1.000000 .
C5 C 0.77713(19) 0.50769(7) 1.03555(18) 0.0181(3) Uani 1.000000 .
C6 C 0.7874(2) 0.57253(8) 0.9915(2) 0.0230(3) Uani 1.000000 .
H6 H 0.8349(2) 0.60228(8) 1.0693(2) 0.0276(4) Uiso 1.000000 R
C7 C 0.7266(2) 0.59238(8) 0.8312(2) 0.0281(4) Uani 1.000000 .
H7 H 0.7324(2) 0.63555(8) 0.8014(2) 0.0337(4) Uiso 1.000000 R
C8 C 0.6566(2) 0.54748(9) 0.7153(2) 0.0297(4) Uani 1.000000 .
H8 H 0.6175(2) 0.56076(9) 0.6073(2) 0.0356(5) Uiso 1.000000 R
C9 C 0.6448(2) 0.48330(8) 0.75911(19) 0.0257(4) Uani 1.000000 .
H9 H 0.5966(2) 0.45377(8) 0.68106(19) 0.0308(4) Uiso 1.000000 R
C10 C 0.70499(19) 0.46279(7) 0.91988(18) 0.0196(3) Uani 1.000000 .
C11 C 0.8859(2) 0.34863(7) 1.52139(19) 0.0207(3) Uani 1.000000 .
H11a H 0.8749(2) 0.35904(7) 1.63999(19) 0.0248(4) Uiso 1.000000 R
H11b H 0.7891(2) 0.31962(7) 1.48762(19) 0.0248(4) Uiso 1.000000 R
C12 C 1.0590(2) 0.31512(7) 1.50194(18) 0.0193(3) Uani 1.000000 .
C13 C 1.1088(2) 0.26120(8) 1.4220(2) 0.0260(4) Uani 1.000000 .
H13 H 1.0346(2) 0.23357(8) 1.3580(2) 0.0312(4) Uiso 1.000000 R
C14 C 1.2972(2) 0.25475(8) 1.4545(2) 0.0279(4) Uani 1.000000 .
H14 H 1.3697(2) 0.22217(8) 1.4160(2) 0.0334(4) Uiso 1.000000 R
C15 C 1.3487(2) 0.30482(8) 1.5512(2) 0.0267(4) Uani 1.000000 .
H15 H 1.4657(2) 0.31258(8) 1.5913(2) 0.0320(4) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.7336(15) .
O1 C4 1.2198(18) .
O2 C1 1.2284(18) .
O3 C12 1.3726(18) .
O3 C15 1.3702(19) .
N1 H1 0.8600 .
N1 C3 1.3409(19) .
N1 C11 1.4690(19) .
C1 C2 1.454(2) .
C1 C10 1.490(2) .
C2 C3 1.370(2) .
C3 C4 1.519(2) .
C4 C5 1.475(2) .
C5 C6 1.396(2) .
C5 C10 1.396(2) .
C6 H6 0.9300 .
C6 C7 1.387(2) .
C7 H7 0.9300 .
C7 C8 1.392(2) .
C8 H8 0.9300 .
C8 C9 1.383(2) .
C9 H9 0.9300 .
C9 C10 1.393(2) .
C11 H11a 0.9700 .
C11 H11b 0.9700 .
C11 C12 1.487(2) .
C12 C13 1.349(2) .
C13 H13 0.9300 .
C13 C14 1.428(2) .
C14 H14 0.9300 .
C14 C15 1.337(2) .
C15 H15 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
C15 O3 C12 106.31(12) . .
C3 N1 H1 114.68(8) . .
C11 N1 H1 114.68(8) . .
C11 N1 C3 130.63(13) . .
C2 C1 O2 121.74(14) . .
C10 C1 O2 120.19(14) . .
C10 C1 C2 118.07(13) . .
C1 C2 Cl1 114.14(11) . .
C3 C2 Cl1 122.46(12) . .
C3 C2 C1 123.37(13) . .
C2 C3 N1 130.82(14) . .
C4 C3 N1 111.01(12) . .
C4 C3 C2 118.17(13) . .
C3 C4 O1 118.81(13) . .
C5 C4 O1 121.75(13) . .
C5 C4 C3 119.43(12) . .
C6 C5 C4 119.97(13) . .
C10 C5 C4 119.54(13) . .
C10 C5 C6 120.49(14) . .
H6 C6 C5 120.13(9) . .
C7 C6 C5 119.73(15) . .
C7 C6 H6 120.13(10) . .
H7 C7 C6 120.12(10) . .
C8 C7 C6 119.76(15) . .
C8 C7 H7 120.12(10) . .
H8 C8 C7 119.69(10) . .
C9 C8 C7 120.62(15) . .
C9 C8 H8 119.69(10) . .
H9 C9 C8 119.93(10) . .
C10 C9 C8 120.15(15) . .
C10 C9 H9 119.93(10) . .
C5 C10 C1 120.95(13) . .
C9 C10 C1 119.81(14) . .
C9 C10 C5 119.24(14) . .
H11a C11 N1 108.88(8) . .
H11b C11 N1 108.88(8) . .
H11b C11 H11a 107.7 . .
C12 C11 N1 113.46(12) . .
C12 C11 H11a 108.88(8) . .
C12 C11 H11b 108.88(8) . .
C11 C12 O3 115.65(13) . .
C13 C12 O3 109.77(13) . .
C13 C12 C11 134.57(15) . .
H13 C13 C12 126.61(10) . .
C14 C13 C12 106.79(14) . .
C14 C13 H13 126.61(9) . .
H14 C14 C13 126.79(9) . .
C15 C14 C13 106.41(14) . .
C15 C14 H14 126.79(10) . .
C14 C15 O3 110.72(14) . .
H15 C15 O3 124.64(9) . .
H15 C15 C14 124.64(10) . .


