# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_7c
_database_code_depnum_ccdc_archive 'CCDC 1547011'
_audit_update_record             
;
2017-04-29 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N2 O3'
_chemical_formula_sum            'C15 H14 N2 O3'
_chemical_formula_weight         270.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   17.132(3)
_cell_length_b                   13.827(3)
_cell_length_c                   5.5861(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1323.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      32.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.222
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   'Scala (Evans, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11370
_diffrn_reflns_av_unetI/netI     0.1384
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.245
_diffrn_reflns_theta_max         38.295
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             2694
_reflns_number_gt                1631
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.893
_reflns_Friedel_fraction_full    0.945

_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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL
_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)+(0.01P)²+1.2P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 561 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2694
_refine_ls_number_parameters     167
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.2300
_refine_ls_wR_factor_gt          0.2070
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.036
_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 0.7036(2) 0.5266(3) 0.6768(14) 0.0617(13) Uani 1 1 d . . . . .
O2 O 0.5412(3) 0.5767(4) 0.0332(14) 0.0708(15) Uani 1 1 d . . . . .
O3 O 0.6804(6) 0.1322(7) 0.7856(18) 0.0701(13) Uani 0.5 1 d D . P A 1
O3' O 0.6844(6) 0.1240(7) 0.6923(18) 0.0701(13) Uani 0.5 1 d D . P B 2
N1 N 0.6270(3) 0.5752(4) 0.3587(15) 0.0560(15) Uani 1 1 d . . . . .
N2 N 0.6367(8) 0.3327(5) 0.5607(19) 0.0701(13) Uani 0.5 1 d D . P A 1
H2A H 0.5928 0.3439 0.6453 0.105 Uiso 0.5 1 d R U P A 1
N2' N 0.6987(6) 0.3331(5) 0.431(3) 0.0701(13) Uani 0.5 1 d D . P B 2
H2B H 0.7405 0.3439 0.3375 0.105 Uiso 0.5 1 d R U P B 2
C2 C 0.6646(3) 0.5074(4) 0.5034(17) 0.0563(16) Uani 1 1 d D . . . .
C3 C 0.6465(5) 0.4091(4) 0.4001(16) 0.085(3) Uani 1 1 d D . . . .
H3A H 0.6989 0.3921 0.3334 0.128 Uiso 0.5 1 calc R U P A 1
H3B H 0.6031 0.3882 0.5081 0.128 Uiso 0.5 1 calc R U P A 2
C4 C 0.6018(4) 0.4258(5) 0.1681(16) 0.0599(17) Uani 1 1 d D . . . .
H4A H 0.6339 0.4082 0.0274 0.072 Uiso 1 1 calc R U . . .
H4B H 0.5529 0.3876 0.1652 0.072 Uiso 1 1 calc R U . . .
C5 C 0.5846(3) 0.5325(5) 0.1709(18) 0.0581(17) Uani 1 1 d . . . . .
C6 C 0.6323(3) 0.6780(5) 0.3897(17) 0.0538(17) Uani 1 1 d . . . . .
C7 C 0.6024(4) 0.7231(5) 0.5962(17) 0.0599(18) Uani 1 1 d . . . . .
H7 H 0.5786 0.6852 0.7178 0.072 Uiso 1 1 calc R U . . .
C8 C 0.6076(4) 0.8217(5) 0.6225(18) 0.0627(18) Uani 1 1 d . . . . .
H8 H 0.5877 0.8515 0.7631 0.075 Uiso 1 1 calc R U . . .
C9 C 0.6422(4) 0.8794(5) 0.4427(17) 0.066(2) Uani 1 1 d . . . . .
H9 H 0.6443 0.9477 0.4593 0.079 Uiso 1 1 calc R U . . .
C10 C 0.6736(4) 0.8338(5) 0.238(2) 0.0636(19) Uani 1 1 d . . . . .
H10 H 0.6980 0.8717 0.1174 0.076 Uiso 1 1 calc R U . . .
C11 C 0.6690(4) 0.7347(5) 0.2112(19) 0.0612(18) Uani 1 1 d . . . . .
H11 H 0.6905 0.7046 0.0733 0.073 Uiso 1 1 calc R U . . .
C12 C 0.6308(9) 0.2335(6) 0.4611(15) 0.0701(13) Uani 0.5 1 d D . P A 1
H12A H 0.5875 0.2304 0.3440 0.084 Uiso 0.5 1 calc R U P A 1
H12B H 0.6798 0.2166 0.3772 0.084 Uiso 0.5 1 calc R U P A 1
C13 C 0.6165(7) 0.1640(5) 0.6570(11) 0.0701(13) Uani 0.5 1 d D . P A 1
C14 C 0.5496(7) 0.1237(8) 0.739(2) 0.0701(13) Uani 0.5 1 d D . P A 1
H14A H 0.4980 0.1337 0.6807 0.084 Uiso 0.5 1 calc R U P A 1
C15 C 0.5735(7) 0.0634(8) 0.929(2) 0.0701(13) Uani 0.5 1 d D . P A 1
H15A H 0.5397 0.0247 1.0236 0.084 Uiso 0.5 1 calc R U P A 1
C16 C 0.6518(7) 0.0690(8) 0.955(2) 0.0701(13) Uani 0.5 1 d D . P A 1
H16A H 0.6820 0.0353 1.0711 0.084 Uiso 0.5 1 calc R U P A 1
C12' C 0.6641(9) 0.2381(7) 0.3672(16) 0.0701(13) Uani 0.5 1 d D . P B 2
H12C H 0.6218 0.2495 0.2499 0.084 Uiso 0.5 1 calc R U P B 2
H12D H 0.7047 0.1992 0.2859 0.084 Uiso 0.5 1 calc R U P B 2
C13' C 0.6320(6) 0.1800(5) 0.5660(12) 0.0701(13) Uani 0.5 1 d D . P B 2
C14' C 0.5603(7) 0.1665(8) 0.663(2) 0.0701(13) Uani 0.5 1 d D . P B 2
H14B H 0.5134 0.1964 0.6098 0.084 Uiso 0.5 1 calc R U P B 2
C15' C 0.5668(7) 0.1007(8) 0.854(2) 0.0701(13) Uani 0.5 1 d D . P B 2
H15B H 0.5258 0.0781 0.9542 0.084 Uiso 0.5 1 calc R U P B 2
C16' C 0.6431(7) 0.0761(8) 0.868(2) 0.0701(13) Uani 0.5 1 d D . P B 2
H16B H 0.6649 0.0324 0.9810 0.084 Uiso 0.5 1 calc R U P B 2


_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 C2 1.206(7) . ?
O2 C5 1.232(8) . ?
O3 C16 1.380(4) . ?
O3 C13 1.381(4) . ?
O3' C16' 1.380(4) . ?
O3' C13' 1.380(4) . ?
N1 C2 1.396(8) . ?
N1 C5 1.406(8) . ?
N1 C6 1.434(8) . ?
N2 C3 1.396(4) . ?
N2 C12 1.485(4) . ?
N2 H2A 0.9003 . ?
N2' C3 1.391(4) . ?
N2' C12' 1.485(4) . ?
N2' H2B 0.9001 . ?
C2 C3 1.508(4) . ?
C3 C4 1.524(4) . ?
C3 H3A 1.0000 . ?
C3 H3B 1.0000 . ?
C4 C5 1.504(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C7 1.407(9) . ?
C6 C11 1.416(9) . ?
C7 C8 1.375(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.412(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.412(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(9) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.476(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.355(4) . ?
C14 C15 1.411(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.353(4) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C12' C13' 1.476(4) . ?
C12' H12C 0.9900 . ?
C12' H12D 0.9900 . ?
C13' C14' 1.355(4) . ?
C14' C15' 1.410(4) . ?
C14' H14B 0.9500 . ?
C15' C16' 1.352(4) . ?
C15' H15B 0.9500 . ?
C16' H16B 0.9500 . ?

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
C16 O3 C13 106.1(10) . . ?
C16' O3' C13' 107.4(9) . . ?
C2 N1 C5 112.8(5) . . ?
C2 N1 C6 124.5(5) . . ?
C5 N1 C6 122.6(5) . . ?
C3 N2 C12 117.8(8) . . ?
C3 N2 H2A 107.9 . . ?
C12 N2 H2A 107.4 . . ?
C3 N2' C12' 112.5(8) . . ?
C3 N2' H2B 108.2 . . ?
C12' N2' H2B 108.9 . . ?
O1 C2 N1 125.0(5) . . ?
O1 C2 C3 128.2(6) . . ?
N1 C2 C3 106.8(5) . . ?
N2' C3 C2 120.1(6) . . ?
N2 C3 C2 117.4(6) . . ?
N2' C3 C4 123.0(7) . . ?
N2 C3 C4 126.9(7) . . ?
C2 C3 C4 107.0(5) . . ?
N2 C3 H3A 99.8 . . ?
C2 C3 H3A 99.8 . . ?
C4 C3 H3A 99.8 . . ?
N2' C3 H3B 100.5 . . ?
C2 C3 H3B 100.5 . . ?
C4 C3 H3B 100.5 . . ?
C5 C4 C3 103.8(5) . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
O2 C5 N1 124.6(6) . . ?
O2 C5 C4 126.7(6) . . ?
N1 C5 C4 108.6(5) . . ?
C7 C6 C11 119.6(6) . . ?
C7 C6 N1 120.9(5) . . ?
C11 C6 N1 119.4(6) . . ?
C8 C7 C6 120.2(6) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.7(7) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 119.0(6) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C11 C10 C9 120.6(7) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C6 119.9(7) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
C13 C12 N2 109.6(6) . . ?
C13 C12 H12A 109.8 . . ?
N2 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
N2 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 O3 111.4(10) . . ?
C14 C13 C12 131.1(10) . . ?
O3 C13 C12 117.5(11) . . ?
C13 C14 C15 104.5(11) . . ?
C13 C14 H14A 127.7 . . ?
C15 C14 H14A 127.7 . . ?
C16 C15 C14 109.7(12) . . ?
C16 C15 H15A 125.2 . . ?
C14 C15 H15A 125.2 . . ?
C15 C16 O3 108.3(11) . . ?
C15 C16 H16A 125.9 . . ?
O3 C16 H16A 125.9 . . ?
C13' C12' N2' 116.6(8) . . ?
C13' C12' H12C 108.1 . . ?
N2' C12' H12C 108.1 . . ?
C13' C12' H12D 108.1 . . ?
N2' C12' H12D 108.1 . . ?
H12C C12' H12D 107.3 . . ?
C14' C13' O3' 108.0(9) . . ?
C14' C13' C12' 135.4(11) . . ?
O3' C13' C12' 116.6(10) . . ?
C13' C14' C15' 108.6(11) . . ?
C13' C14' H14B 125.7 . . ?
C15' C14' H14B 125.7 . . ?
C16' C15' C14' 106.4(12) . . ?
C16' C15' H15B 126.8 . . ?
C14' C15' H15B 126.8 . . ?
C15' C16' O3' 109.6(11) . . ?
C15' C16' H16B 125.2 . . ?
O3' C16' H16B 125.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 O1 -179.2(6) . . . . ?
C6 N1 C2 O1 2.9(10) . . . . ?
C5 N1 C2 C3 0.8(8) . . . . ?
C6 N1 C2 C3 -177.1(6) . . . . ?
C12' N2' C3 C2 167.1(9) . . . . ?
C12' N2' C3 C4 -51.7(13) . . . . ?
C12 N2 C3 C2 -170.9(10) . . . . ?
C12 N2 C3 C4 45.8(15) . . . . ?
O1 C2 C3 N2' -27.9(13) . . . . ?
N1 C2 C3 N2' 152.1(8) . . . . ?
O1 C2 C3 N2 35.5(12) . . . . ?
N1 C2 C3 N2 -144.5(8) . . . . ?
O1 C2 C3 C4 -174.5(7) . . . . ?
N1 C2 C3 C4 5.6(8) . . . . ?
N2' C3 C4 C5 -154.6(8) . . . . ?
N2 C3 C4 C5 137.1(9) . . . . ?
C2 C3 C4 C5 -9.2(8) . . . . ?
C2 N1 C5 O2 173.2(7) . . . . ?
C6 N1 C5 O2 -8.8(10) . . . . ?
C2 N1 C5 C4 -7.0(7) . . . . ?
C6 N1 C5 C4 171.0(5) . . . . ?
C3 C4 C5 O2 -170.4(7) . . . . ?
C3 C4 C5 N1 9.8(7) . . . . ?
C2 N1 C6 C7 -64.8(8) . . . . ?
C5 N1 C6 C7 117.5(7) . . . . ?
C2 N1 C6 C11 114.3(7) . . . . ?
C5 N1 C6 C11 -63.4(8) . . . . ?
C11 C6 C7 C8 1.2(10) . . . . ?
N1 C6 C7 C8 -179.6(6) . . . . ?
C6 C7 C8 C9 0.6(10) . . . . ?
C7 C8 C9 C10 -1.9(11) . . . . ?
C8 C9 C10 C11 1.4(11) . . . . ?
C9 C10 C11 C6 0.4(10) . . . . ?
C7 C6 C11 C10 -1.7(9) . . . . ?
N1 C6 C11 C10 179.2(6) . . . . ?
C3 N2 C12 C13 -177.1(10) . . . . ?
C16 O3 C13 C14 0.00(14) . . . . ?
C16 O3 C13 C12 179.99(10) . . . . ?
N2 C12 C13 C14 97.5(11) . . . . ?
N2 C12 C13 O3 -82.5(11) . . . . ?
O3 C13 C14 C15 -0.02(19) . . . . ?
C12 C13 C14 C15 180.00(10) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C14 C15 C16 O3 0.0(3) . . . . ?
C13 O3 C16 C15 0.01(19) . . . . ?
C3 N2' C12' C13' -96.6(14) . . . . ?
C16' O3' C13' C14' 0.00(14) . . . . ?
C16' O3' C13' C12' -179.99(10) . . . . ?
N2' C12' C13' C14' 96.2(11) . . . . ?
N2' C12' C13' O3' -83.8(11) . . . . ?
O3' C13' C14' C15' 0.04(19) . . . . ?
C12' C13' C14' C15' -179.98(10) . . . . ?
C13' C14' C15' C16' -0.1(2) . . . . ?
C14' C15' C16' O3' 0.1(2) . . . . ?
C13' O3' C16' C15' 0.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2' H2B N2' 0.90 2.50 3.301(11) 148 4_654
C3 H3B O2 1.00 2.52 3.307(10) 135 2_665
C7 H7 O2 0.95 2.40 3.340(8) 170 1_556
C12' H12D O3' 0.99 2.23 3.191(17) 164 4_654

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.064

_shelxl_version_number           2014/6

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

data_7h
_database_code_depnum_ccdc_archive 'CCDC 1547012'
_audit_update_record             
;
2017-04-29 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 N2 O3'
_chemical_formula_sum            'C16 H16 N2 O3'
_chemical_formula_weight         284.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   17.231(3)
_cell_length_b                   14.729(3)
_cell_length_c                   5.6114(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1424.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      33.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'Scala (Evans, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20771
_diffrn_reflns_av_unetI/netI     0.1403
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.483
_diffrn_reflns_theta_max         38.445
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3004
_reflns_number_gt                1676
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.982

_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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL
_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)+(0.01P)²+1.2P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.008(1)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 598 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(8)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3004
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1411
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.1934
_refine_ls_wR_factor_gt          0.1694
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.2947(2) 0.4914(3) 0.3425(9) 0.0559(11) Uani 1 1 d . . . . .
O2 O 0.4593(2) 0.4327(3) 0.9621(9) 0.0614(13) Uani 1 1 d . . . . .
O3 O 0.3296(3) 0.8673(3) 0.3554(11) 0.0744(15) Uani 1 1 d . . . . .
N1 N 0.3736(2) 0.4396(3) 0.6450(9) 0.0480(13) Uani 1 1 d . . . . .
N2 N 0.2997(3) 0.6626(4) 0.6002(13) 0.0731(18) Uani 1 1 d . . . . .
H2 H 0.2600 0.6451 0.7001 0.088 Uiso 1 1 d R U . . .
C2 C 0.3367(3) 0.5070(4) 0.5119(12) 0.0487(16) Uani 1 1 d . . . . .
C3 C 0.3594(4) 0.5983(4) 0.6107(15) 0.063(2) Uani 1 1 d . . . . .
H3 H 0.4006 0.6216 0.5011 0.076 Uiso 1 1 calc R U . . .
C4 C 0.4010(3) 0.5769(4) 0.8430(12) 0.0508(16) Uani 1 1 d . . . . .
H4A H 0.4500 0.6115 0.8553 0.061 Uiso 1 1 calc R U . . .
H4B H 0.3678 0.5918 0.9816 0.061 Uiso 1 1 calc R U . . .
C5 C 0.4168(4) 0.4769(4) 0.8323(13) 0.0530(16) Uani 1 1 d . . . . .
C6 C 0.3661(3) 0.3459(4) 0.6079(13) 0.0489(15) Uani 1 1 d . . . . .
C7 C 0.3947(4) 0.3034(5) 0.4012(13) 0.063(2) Uani 1 1 d . . . . .
H7 H 0.4197 0.3385 0.2816 0.076 Uiso 1 1 calc R U . . .
C8 C 0.3865(4) 0.2114(5) 0.3720(14) 0.0644(19) Uani 1 1 d . . . . .
H8 H 0.4034 0.1844 0.2273 0.077 Uiso 1 1 calc R U . . .
C9 C 0.3546(4) 0.1570(5) 0.5464(15) 0.072(2) Uani 1 1 d . . . . .
H9 H 0.3524 0.0929 0.5283 0.087 Uiso 1 1 calc R U . . .
C10 C 0.3255(4) 0.1994(5) 0.7515(13) 0.0596(19) Uani 1 1 d . . . . .
H10 H 0.3019 0.1638 0.8727 0.072 Uiso 1 1 calc R U . . .
C11 C 0.3306(4) 0.2907(4) 0.7786(13) 0.0535(17) Uani 1 1 d . . . . .
H11 H 0.3094 0.3180 0.9175 0.064 Uiso 1 1 calc R U . . .
C12 C 0.3289(6) 0.7534(5) 0.6737(15) 0.079(2) Uani 1 1 d . . . . .
H12A H 0.2839 0.7904 0.7248 0.095 Uiso 1 1 calc R U . . .
H12B H 0.3628 0.7451 0.8145 0.095 Uiso 1 1 calc R U . . .
C13 C 0.3725(5) 0.8053(6) 0.4932(17) 0.079(3) Uani 1 1 d . . . . .
C14 C 0.4450(5) 0.8019(6) 0.401(2) 0.102(3) Uani 1 1 d . . . . .
H14 H 0.4855 0.7620 0.4484 0.122 Uiso 1 1 calc R U . . .
C15 C 0.4494(5) 0.8685(6) 0.221(2) 0.094(3) Uani 1 1 d . . . . .
H15 H 0.4947 0.8848 0.1340 0.112 Uiso 1 1 calc R U . . .
C16 C 0.3780(4) 0.9054(6) 0.1921(15) 0.072(2) Uani 1 1 d . . . . .
C17 C 0.3436(6) 0.9741(5) 0.0347(19) 0.095(3) Uani 1 1 d . . . . .
H17A H 0.3322 1.0290 0.1268 0.143 Uiso 1 1 calc R U . . .
H17B H 0.2955 0.9503 -0.0343 0.143 Uiso 1 1 calc R U . . .
H17C H 0.3802 0.9888 -0.0933 0.143 Uiso 1 1 calc R 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
O1 C2 1.216(7) . ?
O2 C5 1.221(7) . ?
O3 C16 1.361(10) . ?
O3 C13 1.406(9) . ?
N1 C2 1.396(7) . ?
N1 C5 1.400(8) . ?
N1 C6 1.402(8) . ?
N2 C3 1.399(8) . ?
N2 C12 1.486(9) . ?
N2 H2 0.9211 . ?
C2 C3 1.506(10) . ?
C3 C4 1.521(10) . ?
C3 H3 1.0000 . ?
C4 C5 1.498(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C11 1.397(9) . ?
C6 C7 1.407(10) . ?
C7 C8 1.372(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.402(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.356(9) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.475(12) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.354(12) . ?
C14 C15 1.412(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.354(11) . ?
C15 H15 0.9500 . ?
C16 C17 1.468(12) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
C16 O3 C13 108.4(6) . . ?
C2 N1 C5 111.4(5) . . ?
C2 N1 C6 125.3(5) . . ?
C5 N1 C6 123.2(5) . . ?
C3 N2 C12 110.4(6) . . ?
C3 N2 H2 109.2 . . ?
C12 N2 H2 109.5 . . ?
O1 C2 N1 123.7(6) . . ?
O1 C2 C3 127.6(5) . . ?
N1 C2 C3 108.7(6) . . ?
N2 C3 C2 113.5(5) . . ?
N2 C3 C4 121.6(7) . . ?
C2 C3 C4 104.6(5) . . ?
N2 C3 H3 105.3 . . ?
C2 C3 H3 105.3 . . ?
C4 C3 H3 105.3 . . ?
C5 C4 C3 104.8(6) . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
O2 C5 N1 123.8(6) . . ?
O2 C5 C4 127.5(7) . . ?
N1 C5 C4 108.6(5) . . ?
C11 C6 N1 120.7(6) . . ?
C11 C6 C7 117.4(6) . . ?
N1 C6 C7 121.8(6) . . ?
C8 C7 C6 120.1(6) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 122.0(8) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C10 117.8(7) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
C11 C10 C9 120.7(7) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C6 121.9(7) . . ?
C10 C11 H11 119.1 . . ?
C6 C11 H11 119.1 . . ?
C13 C12 N2 116.7(7) . . ?
C13 C12 H12A 108.1 . . ?
N2 C12 H12A 108.1 . . ?
C13 C12 H12B 108.1 . . ?
N2 C12 H12B 108.1 . . ?
H12A C12 H12B 107.3 . . ?
C14 C13 O3 107.4(8) . . ?
C14 C13 C12 135.5(8) . . ?
O3 C13 C12 116.5(7) . . ?
C13 C14 C15 107.3(8) . . ?
C13 C14 H14 126.3 . . ?
C15 C14 H14 126.3 . . ?
C16 C15 C14 108.4(9) . . ?
C16 C15 H15 125.8 . . ?
C14 C15 H15 125.8 . . ?
C15 C16 O3 108.2(8) . . ?
C15 C16 C17 135.6(9) . . ?
O3 C16 C17 116.2(6) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C5 N1 C2 O1 -178.6(5) . . . . ?
C6 N1 C2 O1 -1.9(8) . . . . ?
C5 N1 C2 C3 2.6(7) . . . . ?
C6 N1 C2 C3 179.3(6) . . . . ?
C12 N2 C3 C2 -173.3(6) . . . . ?
C12 N2 C3 C4 60.5(8) . . . . ?
O1 C2 C3 N2 36.3(10) . . . . ?
N1 C2 C3 N2 -145.0(6) . . . . ?
O1 C2 C3 C4 170.9(6) . . . . ?
N1 C2 C3 C4 -10.3(7) . . . . ?
N2 C3 C4 C5 143.6(6) . . . . ?
C2 C3 C4 C5 13.5(7) . . . . ?
C2 N1 C5 O2 -173.8(6) . . . . ?
C6 N1 C5 O2 9.4(9) . . . . ?
C2 N1 C5 C4 6.5(7) . . . . ?
C6 N1 C5 C4 -170.3(5) . . . . ?
C3 C4 C5 O2 167.7(6) . . . . ?
C3 C4 C5 N1 -12.6(7) . . . . ?
C2 N1 C6 C11 -114.0(6) . . . . ?
C5 N1 C6 C11 62.3(8) . . . . ?
C2 N1 C6 C7 67.0(8) . . . . ?
C5 N1 C6 C7 -116.6(7) . . . . ?
C11 C6 C7 C8 0.6(9) . . . . ?
N1 C6 C7 C8 179.6(6) . . . . ?
C6 C7 C8 C9 -3.7(11) . . . . ?
C7 C8 C9 C10 4.2(11) . . . . ?
C8 C9 C10 C11 -1.6(10) . . . . ?
C9 C10 C11 C6 -1.4(10) . . . . ?
N1 C6 C11 C10 -177.1(5) . . . . ?
C7 C6 C11 C10 1.9(9) . . . . ?
C3 N2 C12 C13 79.7(9) . . . . ?
C16 O3 C13 C14 -4.3(9) . . . . ?
C16 O3 C13 C12 -177.0(6) . . . . ?
N2 C12 C13 C14 -76.3(13) . . . . ?
N2 C12 C13 O3 93.7(8) . . . . ?
O3 C13 C14 C15 5.9(10) . . . . ?
C12 C13 C14 C15 176.6(9) . . . . ?
C13 C14 C15 C16 -5.4(11) . . . . ?
C14 C15 C16 O3 2.7(10) . . . . ?
C14 C15 C16 C17 -178.0(10) . . . . ?
C13 O3 C16 C15 0.9(9) . . . . ?
C13 O3 C16 C17 -178.5(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.92 2.58 3.295(7) 135 4
N2 H2 N2 0.92 2.48 3.287(6) 146 4
C7 H7 O2 0.95 2.37 3.307(8) 170 1_554
C12 H12A O3 0.99 2.38 3.363(10) 175 4

_refine_diff_density_max         0.525
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.062

_shelxl_version_number           2014/6

