# 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_2-(tert-butyl)-7-methyl-4-nitrodibenzo[b,d]furan
_database_code_depnum_ccdc_archive 'CCDC 1042911'
_audit_update_record             
;
2015-01-12 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_date             2014-09-10T10:51:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17  H17  N1  O3'
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.31
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.8713(5)
_cell_length_b                   7.0968(4)
_cell_length_c                   12.0516(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.095(3)
_cell_angle_gamma                90
_cell_volume                     712.55(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.32
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_number            7512
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.799
_diffrn_reflns_theta_max         26.954
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.95
_diffrn_reflns_point_group_measured_fraction_max 0.929
_reflns_number_total             2880
_reflns_number_gt                2240
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0548P)²+0.0976P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.049(6)
_refine_ls_number_reflns         2880
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.12
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.008
_refine_ls_abs_structure_details 
;
 Flack x determined using 795 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.9(10)
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.032

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.1110(2) 0.0567(14) -0.14096(18) 0.0882(9) Uani 1 d . .
O2 O 0.2036(2) 0.0556(15) 0.04647(18) 0.0866(9) Uani 1 d . .
O1 O 0.52192(17) 0.0456(9) 0.16625(13) 0.0433(4) Uani 1 d . .
N1 N 0.2216(2) 0.0482(11) -0.04844(19) 0.0504(5) Uani 1 d . .
C1 C 0.6809(10) 0.2234(7) -0.2967(6) 0.0564(16) Uani 1 d . .
H12 H 0.6893 0.23 -0.374 0.085 Uiso 1 calc . .
H11 H 0.7864 0.217 -0.2383 0.085 Uiso 1 calc . .
H1 H 0.6267 0.3336 -0.2834 0.085 Uiso 1 calc . .
C2 C 0.5864(3) 0.0488(12) -0.28829(19) 0.0435(6) Uani 1 d . .
C3 C 0.5596(3) 0.0511(12) -0.16901(19) 0.0400(5) Uani 1 d . .
C4 C 0.6925(3) 0.0486(12) -0.06456(19) 0.0423(5) Uani 1 d . .
H4 H 0.7955 0.0482 -0.0682 0.051 Uiso 1 calc . .
C5 C 0.6721(2) 0.0469(11) 0.04421(19) 0.0396(5) Uani 1 d . .
C6 C 0.7805(2) 0.0460(11) 0.16534(19) 0.0398(5) Uani 1 d . .
C7 C 0.6838(2) 0.0477(11) 0.23510(19) 0.0398(5) Uani 1 d . .
C8 C 0.7421(3) 0.0440(11) 0.3563(2) 0.0437(6) Uani 1 d . .
H5 H 0.6733 0.0381 0.3996 0.052 Uiso 1 calc . .
C9 C 0.9077(3) 0.0493(12) 0.4120(2) 0.0436(5) Uani 1 d . .
C10 C 0.9798(3) 0.0461(14) 0.5443(2) 0.0564(7) Uani 1 d . .
H2 H 0.9055 -0.0106 0.5764 0.085 Uiso 1 calc . .
H7 H 1.0027 0.1727 0.5734 0.085 Uiso 1 calc . .
H6 H 1.0774 -0.0258 0.5678 0.085 Uiso 1 calc . .
C11 C 0.6826(9) -0.1299(7) -0.2953(6) 0.0550(16) Uani 1 d . .
H17 H 0.6235 -0.2399 -0.2881 0.082 Uiso 1 calc . .
H3 H 0.7844 -0.1282 -0.2322 0.082 Uiso 1 calc . .
H16 H 0.6995 -0.1326 -0.3698 0.082 Uiso 1 calc . .
C12 C 0.4074(3) 0.0459(12) -0.1595(2) 0.0416(5) Uani 1 d . .
H10 H 0.3179 0.0401 -0.2281 0.05 Uiso 1 calc . .
C13 C 0.3850(2) 0.0492(12) -0.0510(2) 0.0405(5) Uani 1 d . .
C14 C 0.5169(2) 0.0461(11) 0.05138(19) 0.0382(5) Uani 1 d . .
C15 C 0.9459(3) 0.0454(12) 0.2213(2) 0.0455(6) Uani 1 d . .
H9 H 1.0144 0.0458 0.1776 0.055 Uiso 1 calc . .
C16 C 1.0060(3) 0.0443(13) 0.3427(2) 0.0481(6) Uani 1 d . .
H8 H 1.1167 0.0401 0.3805 0.058 Uiso 1 calc . .
C17 C 0.4291(3) 0.0445(15) -0.3922(2) 0.0578(7) Uani 1 d . .
H15 H 0.4512 0.0346 -0.4646 0.087 Uiso 1 calc . .
H14 H 0.3702 0.1583 -0.3929 0.087 Uiso 1 calc . .
H13 H 0.3666 -0.062 -0.3846 0.087 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O3 N1 1.208(3) . ?
O2 N1 1.209(3) . ?
O1 C14 1.370(2) . ?
O1 C7 1.390(2) . ?
N1 C13 1.460(3) . ?
C1 C2 1.519(10) . ?
C1 H12 0.96 . ?
C1 H11 0.96 . ?
C1 H1 0.96 . ?
C2 C17 1.522(3) . ?
C2 C3 1.536(3) . ?
C2 C11 1.547(9) . ?
C3 C12 1.395(3) . ?
C3 C4 1.398(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.93 . ?
C5 C14 1.409(3) . ?
C5 C6 1.446(3) . ?
C6 C15 1.389(3) . ?
C6 C7 1.392(3) . ?
C7 C8 1.372(3) . ?
C8 C9 1.390(3) . ?
C8 H5 0.93 . ?
C9 C16 1.400(3) . ?
C9 C10 1.501(3) . ?
C10 H2 0.96 . ?
C10 H7 0.96 . ?
C10 H6 0.96 . ?
C11 H17 0.96 . ?
C11 H3 0.96 . ?
C11 H16 0.96 . ?
C12 C13 1.388(3) . ?
C12 H10 0.93 . ?
C13 C14 1.378(3) . ?
C15 C16 1.375(3) . ?
C15 H9 0.93 . ?
C16 H8 0.93 . ?
C17 H15 0.96 . ?
C17 H14 0.96 . ?
C17 H13 0.96 . ?

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 O1 C7 105.74(15) . . ?
O3 N1 O2 122.8(2) . . ?
O3 N1 C13 118.6(2) . . ?
O2 N1 C13 118.3(2) . . ?
C2 C1 H12 109.5 . . ?
C2 C1 H11 109.5 . . ?
H12 C1 H11 109.5 . . ?
C2 C1 H1 109.5 . . ?
H12 C1 H1 109.5 . . ?
H11 C1 H1 109.5 . . ?
C1 C2 C17 109.4(6) . . ?
C1 C2 C3 108.7(5) . . ?
C17 C2 C3 112.16(18) . . ?
C1 C2 C11 109.75(18) . . ?
C17 C2 C11 107.8(6) . . ?
C3 C2 C11 109.0(5) . . ?
C12 C3 C4 117.8(2) . . ?
C12 C3 C2 122.9(2) . . ?
C4 C3 C2 119.25(18) . . ?
C5 C4 C3 120.58(19) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C14 120.5(2) . . ?
C4 C5 C6 134.32(19) . . ?
C14 C5 C6 105.23(18) . . ?
C15 C6 C7 118.3(2) . . ?
C15 C6 C5 135.6(2) . . ?
C7 C6 C5 106.02(18) . . ?
C8 C7 O1 124.71(18) . . ?
C8 C7 C6 123.9(2) . . ?
O1 C7 C6 111.34(19) . . ?
C7 C8 C9 117.6(2) . . ?
C7 C8 H5 121.2 . . ?
C9 C8 H5 121.2 . . ?
C8 C9 C16 118.9(2) . . ?
C8 C9 C10 120.4(2) . . ?
C16 C9 C10 120.5(2) . . ?
C9 C10 H2 109.5 . . ?
C9 C10 H7 109.5 . . ?
H2 C10 H7 109.5 . . ?
C9 C10 H6 109.5 . . ?
H2 C10 H6 109.5 . . ?
H7 C10 H6 109.5 . . ?
C2 C11 H17 109.5 . . ?
C2 C11 H3 109.5 . . ?
H17 C11 H3 109.5 . . ?
C2 C11 H16 109.5 . . ?
H17 C11 H16 109.5 . . ?
H3 C11 H16 109.5 . . ?
C13 C12 C3 122.2(2) . . ?
C13 C12 H10 118.9 . . ?
C3 C12 H10 118.9 . . ?
C14 C13 C12 119.37(18) . . ?
C14 C13 N1 121.64(19) . . ?
C12 C13 N1 118.9(2) . . ?
O1 C14 C13 128.86(18) . . ?
O1 C14 C5 111.66(18) . . ?
C13 C14 C5 119.5(2) . . ?
C16 C15 C6 118.4(2) . . ?
C16 C15 H9 120.8 . . ?
C6 C15 H9 120.8 . . ?
C15 C16 C9 122.8(2) . . ?
C15 C16 H8 118.6 . . ?
C9 C16 H8 118.6 . . ?
C2 C17 H15 109.5 . . ?
C2 C17 H14 109.5 . . ?
H15 C17 H14 109.5 . . ?
C2 C17 H13 109.5 . . ?
H15 C17 H13 109.5 . . ?
H14 C17 H13 109.5 . . ?

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
C1 C2 C3 C12 122.3(8) . . . . ?
C17 C2 C3 C12 1.2(12) . . . . ?
C11 C2 C3 C12 -118.1(8) . . . . ?
C1 C2 C3 C4 -61.1(8) . . . . ?
C17 C2 C3 C4 177.9(7) . . . . ?
C11 C2 C3 C4 58.5(8) . . . . ?
C12 C3 C4 C5 -1.9(12) . . . . ?
C2 C3 C4 C5 -178.7(7) . . . . ?
C3 C4 C5 C14 0.5(12) . . . . ?
C3 C4 C5 C6 -179.3(8) . . . . ?
C4 C5 C6 C15 -0.5(16) . . . . ?
C14 C5 C6 C15 179.7(10) . . . . ?
C4 C5 C6 C7 178.9(9) . . . . ?
C14 C5 C6 C7 -0.9(8) . . . . ?
C14 O1 C7 C8 -178.6(7) . . . . ?
C14 O1 C7 C6 -1.1(8) . . . . ?
C15 C6 C7 C8 -1.7(12) . . . . ?
C5 C6 C7 C8 178.7(7) . . . . ?
C15 C6 C7 O1 -179.2(7) . . . . ?
C5 C6 C7 O1 1.2(8) . . . . ?
O1 C7 C8 C9 -179.2(8) . . . . ?
C6 C7 C8 C9 3.6(11) . . . . ?
C7 C8 C9 C16 -4.5(11) . . . . ?
C7 C8 C9 C10 179.9(7) . . . . ?
C4 C3 C12 C13 3.7(12) . . . . ?
C2 C3 C12 C13 -179.6(7) . . . . ?
C3 C12 C13 C14 -4.0(12) . . . . ?
C3 C12 C13 N1 178.4(8) . . . . ?
O3 N1 C13 C14 177.8(8) . . . . ?
O2 N1 C13 C14 4.2(13) . . . . ?
O3 N1 C13 C12 -4.6(13) . . . . ?
O2 N1 C13 C12 -178.3(8) . . . . ?
C7 O1 C14 C13 -178.3(7) . . . . ?
C7 O1 C14 C5 0.5(9) . . . . ?
C12 C13 C14 O1 -178.9(7) . . . . ?
N1 C13 C14 O1 -1.4(13) . . . . ?
C12 C13 C14 C5 2.4(12) . . . . ?
N1 C13 C14 C5 179.9(8) . . . . ?
C4 C5 C14 O1 -179.6(7) . . . . ?
C6 C5 C14 O1 0.2(9) . . . . ?
C4 C5 C14 C13 -0.7(12) . . . . ?
C6 C5 C14 C13 179.1(7) . . . . ?
C7 C6 C15 C16 0.7(13) . . . . ?
C5 C6 C15 C16 -179.9(9) . . . . ?
C6 C15 C16 C9 -1.9(13) . . . . ?
C8 C9 C16 C15 3.9(13) . . . . ?
C10 C9 C16 C15 179.5(9) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_AK-5-90
_database_code_depnum_ccdc_archive 'CCDC 1042912'
_audit_update_record             
;
2015-01-12 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_date             2014-10-21T18:37:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13  H8  Cl1  N1  O3'
_chemical_formula_sum            'C13 H8 Cl N O3'
_chemical_formula_weight         261.65

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2089(4)
_cell_length_b                   8.7381(5)
_cell_length_c                   10.2105(6)
_cell_angle_alpha                78.365(2)
_cell_angle_beta                 88.899(2)
_cell_angle_gamma                67.042(2)
_cell_volume                     578.80(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_number            20323
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             2667
_reflns_number_gt                2282
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0574P)²+0.1492P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.043(8)
_refine_ls_number_reflns         2667
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.037
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.103
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.29961(7) -0.56369(5) 1.18924(5) 0.06435(19) Uani 1 d . .
O1 O 0.21944(15) 0.14233(12) 1.06853(9) 0.0400(2) Uani 1 d . .
C5 C 0.2825(2) -0.27319(18) 1.02622(14) 0.0405(3) Uani 1 d . .
H003 H 0.2989 -0.3307 0.9544 0.049 Uiso 1 calc . .
C3 C 0.2539(2) -0.27377(18) 1.26279(14) 0.0420(3) Uani 1 d . .
H004 H 0.2515 -0.3331 1.3513 0.05 Uiso 1 calc . .
C1 C 0.23710(19) -0.02157(16) 1.11006(13) 0.0345(3) Uani 1 d . .
C7 C 0.2628(2) 0.01865(18) 0.88557(13) 0.0369(3) Uani 1 d . .
C6 C 0.26326(19) -0.10517(17) 1.00320(13) 0.0349(3) Uani 1 d . .
C2 C 0.2339(2) -0.10650(18) 1.23982(13) 0.0389(3) Uani 1 d . .
C11 C 0.2245(2) 0.31523(19) 0.84862(15) 0.0456(3) Uani 1 d . .
H009 H 0.2061 0.4128 0.8835 0.055 Uiso 1 calc . .
C4 C 0.2773(2) -0.35437(18) 1.15657(15) 0.0425(3) Uani 1 d . .
C8 C 0.2798(2) 0.0220(2) 0.74864(14) 0.0465(4) Uani 1 d . .
H011 H 0.2989 -0.0757 0.7139 0.056 Uiso 1 calc . .
O3 O 0.2467(3) -0.1154(2) 1.46526(12) 0.0882(5) Uani 1 d . .
C12 C 0.2356(2) 0.16522(18) 0.93084(13) 0.0378(3) Uani 1 d . .
O2 O 0.1608(3) 0.12692(18) 1.33199(14) 0.0938(6) Uani 1 d . .
N1 N 0.2110(2) -0.02510(19) 1.35385(13) 0.0550(4) Uani 1 d . .
C10 C 0.2415(2) 0.3170(2) 0.71277(16) 0.0499(4) Uani 1 d . .
C9 C 0.2681(2) 0.1711(2) 0.66524(15) 0.0525(4) Uani 1 d . .
H017 H 0.2786 0.1749 0.5719 0.063 Uiso 1 calc . .
C13 C 0.2298(3) 0.4767(3) 0.6171(2) 0.0718(6) Uani 1 d . .
H1AA H 0.2919 0.5364 0.6611 0.108 Uiso 1 calc . .
H1AB H 0.088 0.5506 0.5904 0.108 Uiso 1 calc . .
H1AC H 0.3017 0.447 0.5375 0.108 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Cl01 C4 1.7347(14) . ?
O1 C1 1.3645(15) . ?
O1 C12 1.3888(16) . ?
C5 C4 1.384(2) . ?
C5 C6 1.3903(18) . ?
C5 H003 0.95 . ?
C3 C4 1.382(2) . ?
C3 C2 1.3824(19) . ?
C3 H004 0.95 . ?
C1 C2 1.3864(18) . ?
C1 C6 1.4021(18) . ?
C7 C12 1.390(2) . ?
C7 C8 1.397(2) . ?
C7 C6 1.4444(18) . ?
C2 N1 1.4573(19) . ?
C11 C12 1.3806(19) . ?
C11 C10 1.388(2) . ?
C11 H009 0.95 . ?
C8 C9 1.378(2) . ?
C8 H011 0.95 . ?
O3 N1 1.2141(19) . ?
O2 N1 1.2058(19) . ?
C10 C9 1.397(3) . ?
C10 C13 1.507(2) . ?
C9 H017 0.95 . ?
C13 H1AA 0.98 . ?
C13 H1AB 0.98 . ?
C13 H1AC 0.98 . ?

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
C1 O1 C12 105.37(10) . . ?
C4 C5 C6 118.16(13) . . ?
C4 C5 H003 120.9 . . ?
C6 C5 H003 120.9 . . ?
C4 C3 C2 119.74(13) . . ?
C4 C3 H004 120.1 . . ?
C2 C3 H004 120.1 . . ?
O1 C1 C2 127.61(12) . . ?
O1 C1 C6 112.03(11) . . ?
C2 C1 C6 120.36(12) . . ?
C12 C7 C8 118.48(13) . . ?
C12 C7 C6 105.66(11) . . ?
C8 C7 C6 135.85(13) . . ?
C5 C6 C1 120.22(12) . . ?
C5 C6 C7 134.48(13) . . ?
C1 C6 C7 105.31(11) . . ?
C3 C2 C1 119.43(12) . . ?
C3 C2 N1 118.56(12) . . ?
C1 C2 N1 122.01(13) . . ?
C12 C11 C10 116.95(15) . . ?
C12 C11 H009 121.5 . . ?
C10 C11 H009 121.5 . . ?
C3 C4 C5 122.08(13) . . ?
C3 C4 Cl01 118.38(11) . . ?
C5 C4 Cl01 119.53(12) . . ?
C9 C8 C7 118.13(15) . . ?
C9 C8 H011 120.9 . . ?
C7 C8 H011 120.9 . . ?
C11 C12 O1 124.33(13) . . ?
C11 C12 C7 124.04(13) . . ?
O1 C12 C7 111.63(11) . . ?
O2 N1 O3 124.05(15) . . ?
O2 N1 C2 118.23(13) . . ?
O3 N1 C2 117.71(14) . . ?
C11 C10 C9 119.87(14) . . ?
C11 C10 C13 119.81(17) . . ?
C9 C10 C13 120.31(16) . . ?
C8 C9 C10 122.53(14) . . ?
C8 C9 H017 118.7 . . ?
C10 C9 H017 118.7 . . ?
C10 C13 H1AA 109.5 . . ?
C10 C13 H1AB 109.5 . . ?
H1AA C13 H1AB 109.5 . . ?
C10 C13 H1AC 109.5 . . ?
H1AA C13 H1AC 109.5 . . ?
H1AB C13 H1AC 109.5 . . ?

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
C12 O1 C1 C2 178.94(13) . . . . ?
C12 O1 C1 C6 -0.30(14) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C4 C5 C6 C7 179.46(14) . . . . ?
O1 C1 C6 C5 -179.53(11) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
O1 C1 C6 C7 0.37(15) . . . . ?
C2 C1 C6 C7 -178.94(12) . . . . ?
C12 C7 C6 C5 179.59(14) . . . . ?
C8 C7 C6 C5 0.5(3) . . . . ?
C12 C7 C6 C1 -0.28(14) . . . . ?
C8 C7 C6 C1 -179.40(15) . . . . ?
C4 C3 C2 C1 0.2(2) . . . . ?
C4 C3 C2 N1 -179.53(13) . . . . ?
O1 C1 C2 C3 179.92(13) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
O1 C1 C2 N1 -0.4(2) . . . . ?
C6 C1 C2 N1 178.78(13) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C2 C3 C4 Cl01 -179.42(11) . . . . ?
C6 C5 C4 C3 -0.1(2) . . . . ?
C6 C5 C4 Cl01 179.68(10) . . . . ?
C12 C7 C8 C9 -0.2(2) . . . . ?
C6 C7 C8 C9 178.83(15) . . . . ?
C10 C11 C12 O1 -179.32(13) . . . . ?
C10 C11 C12 C7 0.1(2) . . . . ?
C1 O1 C12 C11 179.58(13) . . . . ?
C1 O1 C12 C7 0.10(14) . . . . ?
C8 C7 C12 C11 -0.1(2) . . . . ?
C6 C7 C12 C11 -179.36(13) . . . . ?
C8 C7 C12 O1 179.42(12) . . . . ?
C6 C7 C12 O1 0.12(15) . . . . ?
C3 C2 N1 O2 -168.02(17) . . . . ?
C1 C2 N1 O2 12.3(2) . . . . ?
C3 C2 N1 O3 13.0(2) . . . . ?
C1 C2 N1 O3 -166.68(16) . . . . ?
C12 C11 C10 C9 0.1(2) . . . . ?
C12 C11 C10 C13 179.71(14) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C11 C10 C9 C8 -0.4(2) . . . . ?
C13 C10 C9 C8 -179.99(16) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_AK-5-133
_database_code_depnum_ccdc_archive 'CCDC 1042913'
_audit_update_record             
;
2015-01-12 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_date             2014-12-17T10:56:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13  H8  N1  O4'
_chemical_formula_sum            'C13 H8 N O4'
_chemical_formula_weight         242.2

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3355(3)
_cell_length_b                   10.3916(4)
_cell_length_c                   14.2893(5)
_cell_angle_alpha                82.618(2)
_cell_angle_beta                 86.176(2)
_cell_angle_gamma                84.050(2)
_cell_volume                     1072.82(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#


_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.5
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_number            33794
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.305
_diffrn_reflns_theta_max         25.079
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             3811
_reflns_number_gt                2913
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0515P)²+0.3904P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3811
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.038
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.80303(17) 0.93067(11) -0.06205(8) 0.0373(3) Uani 1 d . .
O5 O 0.87047(18) 0.54755(12) 0.34090(8) 0.0394(3) Uani 1 d . .
O8 O 0.5846(2) 0.50373(14) 0.70721(9) 0.0543(4) Uani 1 d . .
O4 O 0.4885(2) 0.87102(14) 0.29909(10) 0.0556(4) Uani 1 d . .
O6 O 0.9112(3) 0.79796(14) 0.36592(12) 0.0696(5) Uani 1 d . .
O7 O 0.7520(3) 0.88368(14) 0.47737(11) 0.0711(5) Uani 1 d . .
N1 N 0.7275(2) 0.66520(15) 0.03132(12) 0.0445(4) Uani 1 d . .
O2 O 0.7648(3) 0.67473(15) -0.05324(11) 0.0738(5) Uani 1 d . .
O3 O 0.7202(3) 0.56090(14) 0.08020(12) 0.0740(5) Uani 1 d . .
N2 N 0.8124(3) 0.78957(16) 0.43764(12) 0.0471(4) Uani 1 d . .
C20 C 0.7661(2) 0.42974(17) 0.47770(13) 0.0340(4) Uani 1 d . .
C25 C 0.8018(2) 0.55292(17) 0.43199(12) 0.0346(4) Uani 1 d . .
C24 C 0.7667(3) 0.66093(17) 0.47991(13) 0.0364(4) Uani 1 d . .
C6 C 0.7460(2) 1.12207(17) 0.00409(13) 0.0347(4) Uani 1 d . .
C14 C 0.8819(3) 0.41708(17) 0.32750(13) 0.0359(4) Uani 1 d . .
C11 C 0.6901(3) 0.78395(17) 0.07584(12) 0.0346(4) Uani 1 d . .
C10 C 0.6130(3) 0.77670(18) 0.16709(13) 0.0390(4) Uani 1 d . .
H10 H 0.5889 0.6946 0.2005 0.047 Uiso 1 calc . .
C19 C 0.8209(3) 0.34069(17) 0.40843(13) 0.0357(4) Uani 1 d . .
C12 C 0.7273(2) 0.90447(17) 0.02803(12) 0.0332(4) Uani 1 d . .
C7 C 0.6885(2) 1.01643(17) 0.07254(12) 0.0337(4) Uani 1 d . .
C1 C 0.8129(3) 1.06454(17) -0.07531(13) 0.0348(4) Uani 1 d . .
C22 C 0.6571(3) 0.52538(18) 0.61685(13) 0.0387(4) Uani 1 d . .
C9 C 0.5705(3) 0.88984(19) 0.21013(13) 0.0394(4) Uani 1 d . .
C21 C 0.6944(3) 0.41535(18) 0.57011(13) 0.0390(4) Uani 1 d . .
H21 H 0.671 0.3317 0.6011 0.047 Uiso 1 calc . .
C23 C 0.6928(3) 0.64748(18) 0.57237(13) 0.0390(4) Uani 1 d . .
H23 H 0.6667 0.7219 0.605 0.047 Uiso 1 calc . .
C8 C 0.6088(3) 1.01015(18) 0.16378(13) 0.0388(5) Uani 1 d . .
H8 H 0.5811 1.0869 0.1937 0.047 Uiso 1 calc . .
C5 C 0.7460(3) 1.25625(18) 0.00221(14) 0.0430(5) Uani 1 d . .
H5 H 0.7024 1.2983 0.0557 0.052 Uiso 1 calc . .
C2 C 0.8791(3) 1.13245(19) -0.15723(14) 0.0425(5) Uani 1 d . .
H2 H 0.9244 1.0902 -0.2104 0.051 Uiso 1 calc . .
C15 C 0.9467(3) 0.36838(19) 0.24522(14) 0.0430(5) Uani 1 d . .
H15 H 0.9853 0.4234 0.1908 0.052 Uiso 1 calc . .
C18 C 0.8279(3) 0.20609(18) 0.40736(14) 0.0441(5) Uani 1 d . .
H18 H 0.7877 0.1509 0.4614 0.053 Uiso 1 calc . .
C3 C 0.8760(3) 1.2660(2) -0.15798(15) 0.0474(5) Uani 1 d . .
H3 H 0.9192 1.3173 -0.2133 0.057 Uiso 1 calc . .
C4 C 0.8108(3) 1.32636(19) -0.07927(15) 0.0480(5) Uani 1 d . .
H4 H 0.8111 1.4181 -0.0819 0.058 Uiso 1 calc . .
C16 C 0.9525(3) 0.2349(2) 0.24629(15) 0.0485(5) Uani 1 d . .
H16 H 0.9972 0.1967 0.1913 0.058 Uiso 1 calc . .
C26 C 0.5520(3) 0.6112(2) 0.76062(15) 0.0520(5) Uani 1 d . .
H26A H 0.6665 0.6514 0.7629 0.078 Uiso 1 calc . .
H26B H 0.5075 0.5807 0.825 0.078 Uiso 1 calc . .
H26C H 0.4597 0.6756 0.7307 0.078 Uiso 1 calc . .
C17 C 0.8945(3) 0.1553(2) 0.32607(15) 0.0493(5) Uani 1 d . .
H17 H 0.9009 0.0638 0.3245 0.059 Uiso 1 calc . .
C13 C 0.4106(4) 0.9840(2) 0.33927(17) 0.0689(7) Uani 1 d . .
H13A H 0.5089 1.0342 0.3538 0.103 Uiso 1 calc . .
H13B H 0.3384 0.9577 0.3975 0.103 Uiso 1 calc . .
H13C H 0.3308 1.038 0.2942 0.103 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C12 1.373(2) . ?
O1 C1 1.388(2) . ?
O5 C25 1.370(2) . ?
O5 C14 1.387(2) . ?
O8 C22 1.364(2) . ?
O8 C26 1.424(2) . ?
O4 C9 1.369(2) . ?
O4 C13 1.423(3) . ?
O6 N2 1.214(2) . ?
O7 N2 1.222(2) . ?
N1 O2 1.215(2) . ?
N1 O3 1.216(2) . ?
N1 C11 1.453(2) . ?
N2 C24 1.457(2) . ?
C20 C21 1.384(3) . ?
C20 C25 1.402(2) . ?
C20 C19 1.450(3) . ?
C25 C24 1.382(3) . ?
C24 C23 1.390(3) . ?
C6 C1 1.387(3) . ?
C6 C5 1.391(3) . ?
C6 C7 1.451(2) . ?
C14 C15 1.376(3) . ?
C14 C19 1.392(3) . ?
C11 C10 1.383(3) . ?
C11 C12 1.391(2) . ?
C10 C9 1.393(3) . ?
C10 H10 0.95 . ?
C19 C18 1.396(3) . ?
C12 C7 1.392(2) . ?
C7 C8 1.389(2) . ?
C1 C2 1.374(3) . ?
C22 C23 1.386(3) . ?
C22 C21 1.391(3) . ?
C9 C8 1.384(3) . ?
C21 H21 0.95 . ?
C23 H23 0.95 . ?
C8 H8 0.95 . ?
C5 C4 1.376(3) . ?
C5 H5 0.95 . ?
C2 C3 1.384(3) . ?
C2 H2 0.95 . ?
C15 C16 1.381(3) . ?
C15 H15 0.95 . ?
C18 C17 1.376(3) . ?
C18 H18 0.95 . ?
C3 C4 1.391(3) . ?
C3 H3 0.95 . ?
C4 H4 0.95 . ?
C16 C17 1.390(3) . ?
C16 H16 0.95 . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
C17 H17 0.95 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?

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
C12 O1 C1 105.06(13) . . ?
C25 O5 C14 105.58(13) . . ?
C22 O8 C26 118.31(16) . . ?
C9 O4 C13 117.12(16) . . ?
O2 N1 O3 122.93(17) . . ?
O2 N1 C11 118.39(16) . . ?
O3 N1 C11 118.67(16) . . ?
O6 N2 O7 123.22(17) . . ?
O6 N2 C24 118.60(16) . . ?
O7 N2 C24 118.16(17) . . ?
C21 C20 C25 120.67(17) . . ?
C21 C20 C19 134.37(17) . . ?
C25 C20 C19 104.96(15) . . ?
O5 C25 C24 128.20(16) . . ?
O5 C25 C20 112.08(15) . . ?
C24 C25 C20 119.71(16) . . ?
C25 C24 C23 119.95(17) . . ?
C25 C24 N2 121.79(16) . . ?
C23 C24 N2 118.22(16) . . ?
C1 C6 C5 118.95(17) . . ?
C1 C6 C7 105.61(15) . . ?
C5 C6 C7 135.44(17) . . ?
C15 C14 O5 124.64(17) . . ?
C15 C14 C19 123.97(17) . . ?
O5 C14 C19 111.39(15) . . ?
C10 C11 C12 119.57(16) . . ?
C10 C11 N1 119.01(16) . . ?
C12 C11 N1 121.41(16) . . ?
C11 C10 C9 120.02(17) . . ?
C11 C10 H10 120 . . ?
C9 C10 H10 120 . . ?
C14 C19 C18 118.54(17) . . ?
C14 C19 C20 105.99(15) . . ?
C18 C19 C20 135.45(17) . . ?
O1 C12 C11 127.84(16) . . ?
O1 C12 C7 112.25(15) . . ?
C11 C12 C7 119.91(16) . . ?
C8 C7 C12 120.85(16) . . ?
C8 C7 C6 133.84(16) . . ?
C12 C7 C6 105.31(15) . . ?
C2 C1 C6 123.88(17) . . ?
C2 C1 O1 124.35(17) . . ?
C6 C1 O1 111.77(15) . . ?
O8 C22 C23 123.65(17) . . ?
O8 C22 C21 115.52(17) . . ?
C23 C22 C21 120.83(17) . . ?
O4 C9 C8 124.30(17) . . ?
O4 C9 C10 114.72(16) . . ?
C8 C9 C10 120.98(17) . . ?
C20 C21 C22 118.90(17) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C22 C23 C24 119.93(17) . . ?
C22 C23 H23 120 . . ?
C24 C23 H23 120 . . ?
C9 C8 C7 118.64(17) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C4 C5 C6 118.18(18) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C2 C3 116.24(18) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 H2 121.9 . . ?
C14 C15 C16 116.20(18) . . ?
C14 C15 H15 121.9 . . ?
C16 C15 H15 121.9 . . ?
C17 C18 C19 118.34(18) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C2 C3 C4 121.22(19) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 121.53(19) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C15 C16 C17 121.48(19) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
O8 C26 H26A 109.5 . . ?
O8 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O8 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C18 C17 C16 121.45(19) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?



# END of CIF
####################################################################### 
# 
# 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_MS_282_I
_database_code_depnum_ccdc_archive 'CCDC 1042914'
_audit_update_record             
;
2015-01-12 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_date             2014-12-17T14:05:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13  H8  N1  O3  F1'
_chemical_formula_sum            'C13 H8 F N O3'
_chemical_formula_weight         245.2

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   9.2951(8)
_cell_length_b                   17.4748(14)
_cell_length_c                   13.7550(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.270(5)
_cell_angle_gamma                90
_cell_volume                     2198.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.167
_diffrn_reflns_number            49564
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.227
_diffrn_reflns_theta_max         25.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             3911
_reflns_number_gt                2034
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0501P)²+1.0376P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3911
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.3698(2) 0.26265(13) 0.52482(14) 0.0519(6) Uani 1 d . .
O1 O 0.1608(2) 0.75961(12) 0.28129(14) 0.0497(6) Uani 1 d . .
F1 F 0.3705(3) 0.54474(12) 0.55538(15) 0.0866(7) Uani 1 d . .
F2 F 0.0890(2) 0.38968(12) 0.79947(14) 0.0833(7) Uani 1 d . .
N1 N 0.3623(3) 0.63929(19) 0.2281(2) 0.0572(8) Uani 1 d . .
O3 O 0.4545(3) 0.59125(15) 0.21908(19) 0.0773(8) Uani 1 d . .
O2 O 0.3093(3) 0.68276(17) 0.1628(2) 0.0895(9) Uani 1 d . .
N2 N 0.1821(4) 0.39953(18) 0.4689(2) 0.0653(9) Uani 1 d . .
O5 O 0.2652(3) 0.38396(19) 0.4130(2) 0.1064(11) Uani 1 d . .
C8 C 0.0788(3) 0.80404(19) 0.3364(2) 0.0434(8) Uani 1 d . .
O6 O 0.0818(4) 0.44361(17) 0.44772(19) 0.0966(10) Uani 1 d . .
C25 C 0.4414(3) 0.20263(19) 0.5803(2) 0.0458(8) Uani 1 d . .
C14 C 0.2964(3) 0.30135(19) 0.5879(2) 0.0450(8) Uani 1 d . .
C1 C 0.2226(3) 0.70272(18) 0.3437(2) 0.0433(8) Uani 1 d . .
C19 C 0.3194(3) 0.26768(18) 0.6820(2) 0.0449(8) Uani 1 d . .
C20 C 0.4157(3) 0.20413(18) 0.6770(2) 0.0435(8) Uani 1 d . .
C7 C 0.0893(3) 0.77531(18) 0.4318(2) 0.0441(8) Uani 1 d . .
C6 C 0.1831(3) 0.70929(18) 0.4375(2) 0.0443(8) Uani 1 d . .
C15 C 0.2074(4) 0.36410(19) 0.5669(2) 0.0477(8) Uani 1 d . .
C18 C 0.2491(4) 0.2980(2) 0.7546(2) 0.0528(9) Uani 1 d . .
H18 H 0.2621 0.2764 0.819 0.063 Uiso 1 calc . .
C16 C 0.1364(4) 0.39431(19) 0.6386(2) 0.0546(9) Uani 1 d . .
H16 H 0.0732 0.4372 0.6253 0.066 Uiso 1 calc . .
C2 C 0.3143(3) 0.64534(19) 0.3239(2) 0.0466(8) Uani 1 d . .
C11 C -0.0686(4) 0.8765(2) 0.4615(2) 0.0558(9) Uani 1 d . .
H11 H -0.1215 0.9022 0.5048 0.067 Uiso 1 calc . .
C9 C 0.0002(3) 0.86674(19) 0.3013(2) 0.0507(9) Uani 1 d . .
H9 H -0.0025 0.8842 0.2356 0.061 Uiso 1 calc . .
C24 C 0.5262(4) 0.14922(19) 0.5444(2) 0.0520(9) Uani 1 d . .
H24 H 0.5406 0.1507 0.4778 0.062 Uiso 1 calc . .
C12 C 0.0123(4) 0.8134(2) 0.4955(2) 0.0534(9) Uani 1 d . .
H12 H 0.0159 0.7958 0.5613 0.064 Uiso 1 calc . .
C23 C 0.5900(4) 0.09325(19) 0.6087(3) 0.0548(9) Uani 1 d . .
C17 C 0.1612(4) 0.3597(2) 0.7298(2) 0.0543(9) Uani 1 d . .
C3 C 0.3647(4) 0.5921(2) 0.3961(3) 0.0557(9) Uani 1 d . .
H3 H 0.4272 0.5516 0.3838 0.067 Uiso 1 calc . .
C5 C 0.2346(4) 0.6563(2) 0.5098(2) 0.0546(9) Uani 1 d . .
H5 H 0.21 0.6596 0.5738 0.066 Uiso 1 calc . .
C10 C -0.0762(4) 0.90455(19) 0.3652(2) 0.0519(9) Uani 1 d . .
C4 C 0.3218(4) 0.5993(2) 0.4862(2) 0.0583(10) Uani 1 d . .
C21 C 0.4822(4) 0.1482(2) 0.7416(3) 0.0564(9) Uani 1 d . .
H21 H 0.4687 0.1475 0.8085 0.068 Uiso 1 calc . .
C22 C 0.5678(4) 0.0939(2) 0.7071(3) 0.0610(10) Uani 1 d . .
H22 H 0.6133 0.0556 0.7512 0.073 Uiso 1 calc . .
C13 C -0.1640(4) 0.9750(2) 0.3320(3) 0.0692(11) Uani 1 d . .
H13A H -0.1187 1.0195 0.3686 0.104 Uiso 1 calc . .
H13B H -0.2638 0.9687 0.3445 0.104 Uiso 1 calc . .
H13C H -0.1667 0.9828 0.2611 0.104 Uiso 1 calc . .
C26 C 0.6825(4) 0.0315(2) 0.5741(3) 0.0759(12) Uani 1 d . .
H26A H 0.7859 0.0418 0.5997 0.114 Uiso 1 calc . .
H26B H 0.666 0.0309 0.5017 0.114 Uiso 1 calc . .
H26C H 0.6557 -0.0183 0.5984 0.114 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O4 C14 1.374(3) . ?
O4 C25 1.395(4) . ?
O1 C1 1.371(3) . ?
O1 C8 1.402(3) . ?
F1 C4 1.366(4) . ?
F2 C17 1.369(3) . ?
N1 O2 1.213(4) . ?
N1 O3 1.221(3) . ?
N1 C2 1.468(4) . ?
N2 O6 1.205(3) . ?
N2 O5 1.214(3) . ?
N2 C15 1.464(4) . ?
C8 C9 1.357(4) . ?
C8 C7 1.391(4) . ?
C25 C24 1.369(4) . ?
C25 C20 1.393(4) . ?
C14 C15 1.373(4) . ?
C14 C19 1.403(4) . ?
C1 C2 1.375(4) . ?
C1 C6 1.408(4) . ?
C19 C18 1.392(4) . ?
C19 C20 1.436(4) . ?
C20 C21 1.390(4) . ?
C7 C12 1.395(4) . ?
C7 C6 1.440(4) . ?
C6 C5 1.381(4) . ?
C15 C16 1.384(4) . ?
C18 C17 1.359(4) . ?
C18 H18 0.95 . ?
C16 C17 1.375(4) . ?
C16 H16 0.95 . ?
C2 C3 1.381(4) . ?
C11 C12 1.369(4) . ?
C11 C10 1.403(4) . ?
C11 H11 0.95 . ?
C9 C10 1.392(4) . ?
C9 H9 0.95 . ?
C24 C23 1.379(4) . ?
C24 H24 0.95 . ?
C12 H12 0.95 . ?
C23 C22 1.406(5) . ?
C23 C26 1.508(5) . ?
C3 C4 1.374(4) . ?
C3 H3 0.95 . ?
C5 C4 1.360(4) . ?
C5 H5 0.95 . ?
C10 C13 1.503(4) . ?
C21 C22 1.376(4) . ?
C21 H21 0.95 . ?
C22 H22 0.95 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?

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 O4 C25 105.5(2) . . ?
C1 O1 C8 105.7(2) . . ?
O2 N1 O3 123.7(3) . . ?
O2 N1 C2 118.2(3) . . ?
O3 N1 C2 118.2(3) . . ?
O6 N2 O5 122.9(3) . . ?
O6 N2 C15 118.9(3) . . ?
O5 N2 C15 118.2(3) . . ?
C9 C8 C7 124.8(3) . . ?
C9 C8 O1 124.4(3) . . ?
C7 C8 O1 110.9(3) . . ?
C24 C25 C20 124.4(3) . . ?
C24 C25 O4 124.4(3) . . ?
C20 C25 O4 111.2(3) . . ?
C15 C14 O4 127.5(3) . . ?
C15 C14 C19 121.1(3) . . ?
O4 C14 C19 111.4(3) . . ?
O1 C1 C2 127.6(3) . . ?
O1 C1 C6 111.5(3) . . ?
C2 C1 C6 120.9(3) . . ?
C18 C19 C14 119.2(3) . . ?
C18 C19 C20 134.9(3) . . ?
C14 C19 C20 105.9(3) . . ?
C21 C20 C25 117.7(3) . . ?
C21 C20 C19 136.3(3) . . ?
C25 C20 C19 106.0(3) . . ?
C8 C7 C12 117.5(3) . . ?
C8 C7 C6 106.3(3) . . ?
C12 C7 C6 136.2(3) . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 134.8(3) . . ?
C1 C6 C7 105.7(3) . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 N2 121.5(3) . . ?
C16 C15 N2 118.4(3) . . ?
C17 C18 C19 117.4(3) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 H18 121.3 . . ?
C17 C16 C15 117.3(3) . . ?
C17 C16 H16 121.4 . . ?
C15 C16 H16 121.4 . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 N1 121.9(3) . . ?
C3 C2 N1 118.6(3) . . ?
C12 C11 C10 122.4(3) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C8 C9 C10 117.5(3) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
C25 C24 C23 117.5(3) . . ?
C25 C24 H24 121.2 . . ?
C23 C24 H24 121.2 . . ?
C11 C12 C7 118.8(3) . . ?
C11 C12 H12 120.6 . . ?
C7 C12 H12 120.6 . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 C26 120.6(3) . . ?
C22 C23 C26 119.9(3) . . ?
C18 C17 F2 118.4(3) . . ?
C18 C17 C16 125.0(3) . . ?
F2 C17 C16 116.6(3) . . ?
C4 C3 C2 118.1(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C4 C5 C6 117.6(3) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 C13 120.5(3) . . ?
C11 C10 C13 120.5(3) . . ?
C5 C4 F1 118.8(3) . . ?
C5 C4 C3 124.4(3) . . ?
F1 C4 C3 116.8(3) . . ?
C22 C21 C20 118.9(3) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C23 122.0(3) . . ?
C21 C22 H22 119 . . ?
C23 C22 H22 119 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?



# END of CIF
####################################################################### 
# 
# 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_MS-298
_database_code_depnum_ccdc_archive 'CCDC 1042915'
_audit_update_record             
;
2015-01-12 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_date             2014-12-17T17:30:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13  H12  N1  O2  Cl1'
_chemical_formula_sum            'C13 H12 Cl N O2'
_chemical_formula_weight         249.69

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   17.0453(11)
_cell_length_b                   4.0783(3)
_cell_length_c                   18.9440(12)
_cell_angle_alpha                90
_cell_angle_beta                 115.131(3)
_cell_angle_gamma                90
_cell_volume                     1192.25(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#


_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_number            14459
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.349
_diffrn_reflns_theta_max         25.113
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             2115
_reflns_number_gt                1913
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0552P)²+0.5933P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2115
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.40842(3) -0.02383(15) 0.35913(3) 0.0530(2) Uani 1 d . .
O1 O 0.15403(8) 0.4729(3) 0.46634(7) 0.0416(3) Uani 1 d . .
H1 H 0.1537 0.3629 0.5024 0.062 Uiso 1 calc . .
O2 O 0.40860(8) 0.4720(3) 0.82221(7) 0.0457(4) Uani 1 d . .
N004 N 0.19890(9) 0.0434(4) 0.58350(8) 0.0360(4) Uani 1 d . .
H00A H 0.1682 -0.014 0.6076 0.043 Uiso 1 calc . .
H00B H 0.1804 0.0057 0.5344 0.043 Uiso 1 calc . .
C2 C 0.27970(10) 0.1999(4) 0.62459(9) 0.0300(4) Uani 1 d . .
C7 C 0.29839(10) 0.2603(4) 0.49883(9) 0.0316(4) Uani 1 d . .
C1 C 0.32784(10) 0.3054(4) 0.58430(9) 0.0305(4) Uani 1 d . .
C12 C 0.35659(11) 0.1442(5) 0.47069(10) 0.0353(4) Uani 1 d . .
H12 H 0.4118 0.0798 0.5056 0.042 Uiso 1 calc . .
C8 C 0.21530(11) 0.3505(4) 0.44398(10) 0.0342(4) Uani 1 d . .
C3 C 0.30949(10) 0.2607(4) 0.70367(9) 0.0325(4) Uani 1 d . .
H3 H 0.2769 0.1918 0.7298 0.039 Uiso 1 calc . .
C4 C 0.38729(11) 0.4231(4) 0.74444(9) 0.0334(4) Uani 1 d . .
C11 C 0.33326(11) 0.1236(5) 0.39171(10) 0.0369(4) Uani 1 d . .
C6 C 0.40659(11) 0.4600(4) 0.62760(10) 0.0352(4) Uani 1 d . .
H6 H 0.4401 0.5261 0.6021 0.042 Uiso 1 calc . .
C5 C 0.43746(11) 0.5200(4) 0.70687(10) 0.0375(4) Uani 1 d . .
H5 H 0.4906 0.6228 0.7341 0.045 Uiso 1 calc . .
C9 C 0.19343(12) 0.3293(5) 0.36480(10) 0.0414(4) Uani 1 d . .
H9 H 0.1383 0.3927 0.3292 0.05 Uiso 1 calc . .
C10 C 0.25184(12) 0.2162(5) 0.33794(10) 0.0419(4) Uani 1 d . .
H10 H 0.2368 0.2025 0.2847 0.05 Uiso 1 calc . .
C13 C 0.48671(12) 0.6484(6) 0.86700(11) 0.0505(5) Uani 1 d . .
H13A H 0.5354 0.5295 0.8672 0.076 Uiso 1 calc . .
H13B H 0.493 0.6729 0.9195 0.076 Uiso 1 calc . .
H13C H 0.4841 0.8609 0.8443 0.076 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C11 1.7480(17) . ?
O1 C8 1.377(2) . ?
O1 H1 0.82 . ?
O2 C4 1.374(2) . ?
O2 C13 1.432(2) . ?
N004 C2 1.414(2) . ?
N004 H00A 0.86 . ?
N004 H00B 0.86 . ?
C2 C3 1.385(2) . ?
C2 C1 1.405(2) . ?
C7 C12 1.393(2) . ?
C7 C8 1.404(2) . ?
C7 C1 1.489(2) . ?
C1 C6 1.392(2) . ?
C12 C11 1.378(2) . ?
C12 H12 0.93 . ?
C8 C9 1.386(2) . ?
C3 C4 1.387(2) . ?
C3 H3 0.93 . ?
C4 C5 1.382(3) . ?
C11 C10 1.380(2) . ?
C6 C5 1.386(2) . ?
C6 H6 0.93 . ?
C5 H5 0.93 . ?
C9 C10 1.376(3) . ?
C9 H9 0.93 . ?
C10 H10 0.93 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?

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
C8 O1 H1 109.5 . . ?
C4 O2 C13 117.66(14) . . ?
C2 N004 H00A 120 . . ?
C2 N004 H00B 120 . . ?
H00A N004 H00B 120 . . ?
C3 C2 C1 120.17(15) . . ?
C3 C2 N004 120.02(14) . . ?
C1 C2 N004 119.75(14) . . ?
C12 C7 C8 117.67(15) . . ?
C12 C7 C1 119.47(14) . . ?
C8 C7 C1 122.73(15) . . ?
C6 C1 C2 117.28(15) . . ?
C6 C1 C7 119.49(14) . . ?
C2 C1 C7 123.24(14) . . ?
C11 C12 C7 120.80(15) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
O1 C8 C9 117.71(15) . . ?
O1 C8 C7 121.74(15) . . ?
C9 C8 C7 120.51(16) . . ?
C2 C3 C4 120.83(15) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
O2 C4 C5 124.82(16) . . ?
O2 C4 C3 114.91(15) . . ?
C5 C4 C3 120.27(15) . . ?
C12 C11 C10 121.39(16) . . ?
C12 C11 Cl1 119.18(13) . . ?
C10 C11 Cl1 119.43(13) . . ?
C5 C6 C1 123.09(15) . . ?
C5 C6 H6 118.5 . . ?
C1 C6 H6 118.5 . . ?
C4 C5 C6 118.31(16) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C10 C9 C8 121.11(16) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 118.51(16) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?



# END of CIF
