# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_nj822s
_database_code_depnum_ccdc_archive 'CCDC 1510178'
_audit_update_record             
;
2016-10-16 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
;
3,4-dihydro-(3Z)-(2-oxohex-5-enylidene)-1,4-benzoxazin-2-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 N1 O3'
_chemical_formula_sum            'C14 H13 N1 O3'
_chemical_formula_weight         243.25

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        P21/n
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.2032(8)
_cell_length_b                   4.6426(3)
_cell_length_c                   18.5046(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.389(6)
_cell_angle_gamma                90.00
_cell_volume                     1203.84(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    987
_cell_measurement_theta_min      4.7000
_cell_measurement_theta_max      26.6490

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_reflns_number            4778
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.907
_diffrn_reflns_theta_max         29.003
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2717
_reflns_number_gt                1738
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0410P)²+0.1132P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2717
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
O1 O 0.31465(9) 0.3528(3) 1.03942(6) 0.0583(3) Uani 1 1 d . . . . .
O2 O 0.42531(9) 0.6836(3) 1.04758(6) 0.0685(4) Uani 1 1 d . . . . .
O3 O 0.31354(8) 0.7524(3) 0.77745(6) 0.0572(4) Uani 1 1 d . . . . .
N1 N 0.27061(10) 0.4365(3) 0.89008(7) 0.0448(4) Uani 1 1 d . . . . .
C1 C 0.36484(13) 0.5529(4) 1.00861(8) 0.0500(4) Uani 1 1 d . . . . .
C2 C 0.34198(11) 0.5975(3) 0.92766(8) 0.0425(4) Uani 1 1 d . . . . .
C3 C 0.21768(11) 0.2424(3) 0.92345(8) 0.0430(4) Uani 1 1 d . . . . .
C4 C 0.14246(12) 0.0870(4) 0.88537(9) 0.0527(5) Uani 1 1 d . . . . .
H4 H 0.1258 0.1115 0.8350 0.063 Uiso 1 1 calc R U . . .
C5 C 0.09211(13) -0.1031(4) 0.92125(10) 0.0608(5) Uani 1 1 d . . . . .
H5 H 0.0413 -0.2052 0.8952 0.073 Uiso 1 1 calc R U . . .
C6 C 0.11667(14) -0.1434(4) 0.99607(11) 0.0645(5) Uani 1 1 d . . . . .
H6 H 0.0828 -0.2732 1.0202 0.077 Uiso 1 1 calc R U . . .
C7 C 0.19129(14) 0.0092(4) 1.03455(9) 0.0602(5) Uani 1 1 d . . . . .
H7 H 0.2084 -0.0175 1.0848 0.072 Uiso 1 1 calc R U . . .
C8 C 0.24045(12) 0.2015(4) 0.99844(8) 0.0480(4) Uani 1 1 d . . . . .
C9 C 0.39385(11) 0.7955(3) 0.89781(8) 0.0459(4) Uani 1 1 d . . . . .
H9 H 0.4419 0.8923 0.9286 0.055 Uiso 1 1 calc R U . . .
C10 C 0.37884(12) 0.8650(4) 0.82070(8) 0.0452(4) Uani 1 1 d . . . . .
C11 C 0.44796(12) 1.0659(4) 0.79425(9) 0.0501(4) Uani 1 1 d . . . . .
H11A H 0.4608 1.2269 0.8278 0.060 Uiso 1 1 calc R U . . .
H11B H 0.4206 1.1411 0.7465 0.060 Uiso 1 1 calc R U . . .
C12 C 0.54082(12) 0.9078(4) 0.78900(10) 0.0585(5) Uani 1 1 d . . . . .
H12A H 0.5674 0.8345 0.8371 0.070 Uiso 1 1 calc R U . . .
H12B H 0.5265 0.7438 0.7566 0.070 Uiso 1 1 calc R U . . .
C13 C 0.61339(14) 1.0868(5) 0.76198(12) 0.0745(6) Uani 1 1 d . . . . .
H13 H 0.6353 1.2480 0.7895 0.089 Uiso 1 1 calc R U . . .
C14 C 0.64900(18) 1.0387(7) 0.70350(15) 0.1158(10) Uani 1 1 d . . . . .
H14A H 0.6290 0.8797 0.6744 0.139 Uiso 1 1 calc R U . . .
H14B H 0.6947 1.1629 0.6903 0.139 Uiso 1 1 calc R U . . .
H1N H 0.2601(12) 0.471(4) 0.8430(10) 0.061(5) 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
O1 C1 1.352(2) . ?
O1 C8 1.385(2) . ?
O2 C1 1.1933(19) . ?
O3 C10 1.2376(18) . ?
N1 C2 1.357(2) . ?
N1 C3 1.382(2) . ?
N1 H1N 0.874(18) . ?
C1 C2 1.494(2) . ?
C2 C9 1.351(2) . ?
C3 C4 1.383(2) . ?
C3 C8 1.386(2) . ?
C4 C5 1.373(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(2) . ?
C7 H7 0.9300 . ?
C9 C10 1.444(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.493(2) . ?
C11 C12 1.526(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.473(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.287(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9300 . ?
C14 H14B 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
C1 O1 C8 121.59(12) . . ?
C2 N1 C3 123.07(13) . . ?
C2 N1 H1N 113.7(12) . . ?
C3 N1 H1N 123.2(12) . . ?
O2 C1 O1 118.13(15) . . ?
O2 C1 C2 123.54(17) . . ?
O1 C1 C2 118.33(15) . . ?
C9 C2 N1 125.24(14) . . ?
C9 C2 C1 117.41(15) . . ?
N1 C2 C1 117.35(15) . . ?
N1 C3 C4 122.94(14) . . ?
N1 C3 C8 118.81(15) . . ?
C4 C3 C8 118.26(16) . . ?
C5 C4 C3 120.58(16) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.28(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 119.75(18) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C6 119.61(16) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 O1 117.74(14) . . ?
C7 C8 C3 121.51(17) . . ?
O1 C8 C3 120.74(15) . . ?
C2 C9 C10 123.60(15) . . ?
C2 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
O3 C10 C9 121.25(15) . . ?
O3 C10 C11 121.01(14) . . ?
C9 C10 C11 117.67(15) . . ?
C10 C11 C12 109.96(13) . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 114.20(15) . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 125.5(2) . . ?
C14 C13 H13 117.3 . . ?
C12 C13 H13 117.3 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?

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
C8 O1 C1 O2 177.02(15) . . . . ?
C8 O1 C1 C2 -3.3(2) . . . . ?
C3 N1 C2 C9 -178.04(15) . . . . ?
C3 N1 C2 C1 1.8(2) . . . . ?
O2 C1 C2 C9 0.6(2) . . . . ?
O1 C1 C2 C9 -179.06(14) . . . . ?
O2 C1 C2 N1 -179.22(16) . . . . ?
O1 C1 C2 N1 1.1(2) . . . . ?
C2 N1 C3 C4 177.31(15) . . . . ?
C2 N1 C3 C8 -2.5(2) . . . . ?
N1 C3 C4 C5 -179.96(15) . . . . ?
C8 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 O1 179.43(16) . . . . ?
C6 C7 C8 C3 -1.1(3) . . . . ?
C1 O1 C8 C7 -177.88(15) . . . . ?
C1 O1 C8 C3 2.7(2) . . . . ?
N1 C3 C8 C7 -179.18(14) . . . . ?
C4 C3 C8 C7 1.0(2) . . . . ?
N1 C3 C8 O1 0.2(2) . . . . ?
C4 C3 C8 O1 -179.54(14) . . . . ?
N1 C2 C9 C10 0.9(3) . . . . ?
C1 C2 C9 C10 -178.97(14) . . . . ?
C2 C9 C10 O3 3.1(2) . . . . ?
C2 C9 C10 C11 -173.85(14) . . . . ?
O3 C10 C11 C12 -100.31(18) . . . . ?
C9 C10 C11 C12 76.61(18) . . . . ?
C10 C11 C12 C13 178.92(16) . . . . ?
C11 C12 C13 C14 -119.1(2) . . . . ?

_refine_diff_density_max         0.127
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.032

_shelxl_version_number           2014/6

