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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1481520'
_audit_update_record             
;
2016-05-23 deposited with the CCDC.
2016-07-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-(4-nitrophenoxy)-1-phenylethanone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O4'
_chemical_formula_weight         257.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0930(5)
_cell_length_b                   13.1790(7)
_cell_length_c                   11.4120(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.431(19)
_cell_angle_gamma                90
_cell_volume                     1216.80(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    202
_cell_measurement_theta_min      7.149
_cell_measurement_theta_max      49.966

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6420
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.361
_diffrn_reflns_theta_max         25.699
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2258
_reflns_number_gt                1849
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0512P)²+0.2573P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2258
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.27315(18) 0.65718(11) -0.02362(13) 0.0452(4) Uani 1 1 d . . . . .
C8 C 0.1506(2) 0.41834(11) 0.10973(13) 0.0514(4) Uani 1 1 d . . . . .
C2 C 0.2603(2) 0.75559(11) 0.01902(14) 0.0517(4) Uani 1 1 d . . . . .
H2 H 0.2067 0.7676 0.0888 0.062 Uiso 1 1 calc R U . . .
C3 C 0.3265(2) 0.83509(11) -0.04170(14) 0.0525(4) Uani 1 1 d . . . . .
H3 H 0.3190 0.9010 -0.0133 0.063 Uiso 1 1 calc R U . . .
C4 C 0.40451(18) 0.81554(11) -0.14566(13) 0.0473(4) Uani 1 1 d . . . . .
C5 C 0.41964(18) 0.71848(12) -0.18862(13) 0.0498(4) Uani 1 1 d . . . . .
H5 H 0.4739 0.7070 -0.2583 0.060 Uiso 1 1 calc R U . . .
C6 C 0.3534(2) 0.63812(11) -0.12731(14) 0.0494(4) Uani 1 1 d . . . . .
C9 C 0.14893(18) 0.30638(11) 0.09749(13) 0.0463(4) Uani 1 1 d . . . . .
C7 C 0.22587(19) 0.48137(10) 0.01504(13) 0.0486(4) Uani 1 1 d . . . . .
H7A H 0.3431 0.4670 0.0105 0.058 Uiso 1 1 calc R U . . .
H7B H 0.1736 0.4659 -0.0603 0.058 Uiso 1 1 calc R U . . .
C14 C 0.0781(2) 0.25072(13) 0.18692(15) 0.0599(4) Uani 1 1 d . . . . .
H14 H 0.0364 0.2843 0.2515 0.072 Uiso 1 1 calc R U . . .
C10 C 0.2105(2) 0.25596(12) 0.00165(16) 0.0563(4) Uani 1 1 d . . . . .
N4 N 0.47330(17) 0.89998(10) -0.21056(13) 0.0582(4) Uani 1 1 d . . . . .
O1 O 0.0907(2) 0.45848(10) 0.19335(12) 0.0971(5) Uani 1 1 d . . . . .
O2 O 0.20111(14) 0.58491(7) 0.04355(9) 0.0557(3) Uani 1 1 d . . . . .
O3 O 0.4663(2) 0.98550(9) -0.16850(14) 0.0882(5) Uani 1 1 d . . . . .
O4 O 0.53735(17) 0.88264(10) -0.30477(11) 0.0740(4) Uani 1 1 d . . . . .
C12 C 0.1302(3) 0.09762(14) 0.0856(2) 0.0763(6) Uani 1 1 d . . . . .
H12 H 0.1240 0.0272 0.0814 0.092 Uiso 1 1 calc R U . . .
C13 C 0.0689(3) 0.14712(14) 0.1810(2) 0.0724(6) Uani 1 1 d . . . . .
C11 C 0.2008(3) 0.15121(14) -0.00404(19) 0.0730(5) Uani 1 1 d . . . . .
H11 H 0.2420 0.1170 -0.0683 0.088 Uiso 1 1 calc R U . . .
H6 H 0.365(2) 0.5720(17) -0.1563(17) 0.088 Uiso 1 1 d . U . . .
H10 H 0.261(3) 0.2933(16) -0.0604(18) 0.088 Uiso 1 1 d . U . . .
H13 H 0.016(2) 0.1080(17) 0.2436(18) 0.088 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.3627(17) . ?
C1 C6 1.387(2) . ?
C1 C2 1.390(2) . ?
C8 O1 1.2033(19) . ?
C8 C9 1.482(2) . ?
C8 C7 1.504(2) . ?
C2 C3 1.372(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(2) . ?
C4 N4 1.455(2) . ?
C5 C6 1.385(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.94(2) . ?
C9 C10 1.383(2) . ?
C9 C14 1.392(2) . ?
C7 O2 1.4182(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 C13 1.369(3) . ?
C14 H14 0.9300 . ?
C10 C11 1.384(2) . ?
C10 H10 0.96(2) . ?
N4 O4 1.2267(19) . ?
N4 O3 1.2269(19) . ?
C12 C13 1.372(3) . ?
C12 C11 1.379(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.99(2) . ?
C11 H11 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
O2 C1 C6 124.71(13) . . ?
O2 C1 C2 114.73(13) . . ?
C6 C1 C2 120.56(14) . . ?
O1 C8 C9 120.63(15) . . ?
O1 C8 C7 120.35(14) . . ?
C9 C8 C7 119.01(13) . . ?
C3 C2 C1 120.12(14) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 118.93(14) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.71(14) . . ?
C5 C4 N4 119.39(14) . . ?
C3 C4 N4 118.89(13) . . ?
C4 C5 C6 119.46(14) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 119.21(14) . . ?
C5 C6 H6 119.3(13) . . ?
C1 C6 H6 121.5(13) . . ?
C10 C9 C14 119.32(15) . . ?
C10 C9 C8 123.38(14) . . ?
C14 C9 C8 117.28(14) . . ?
O2 C7 C8 107.73(12) . . ?
O2 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
O2 C7 H7B 110.2 . . ?
C8 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C13 C14 C9 120.80(18) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C9 C10 C11 119.69(18) . . ?
C9 C10 H10 120.3(12) . . ?
C11 C10 H10 120.0(12) . . ?
O4 N4 O3 122.60(14) . . ?
O4 N4 C4 118.63(14) . . ?
O3 N4 C4 118.78(14) . . ?
C1 O2 C7 118.59(11) . . ?
C13 C12 C11 120.64(17) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.56(19) . . ?
C14 C13 H13 120.6(13) . . ?
C12 C13 H13 119.8(13) . . ?
C12 C11 C10 120.00(19) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.031

