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

data_ead29twin
_audit_creation_date              2016-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
;
# end Validation Reply Form
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C15 H14 N2 O5'
_chemical_formula_sum             'C15 H14 N2 O5'
_chemical_formula_weight          302.28
_chemical_melting_point           ?
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'

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

_cell_length_a                    4.8131(5)
_cell_length_b                    11.3992(12)
_cell_length_c                    13.8148(14)
_cell_angle_alpha                 92.391(4)
_cell_angle_beta                  98.154(4)
_cell_angle_gamma                 101.569(3)
_cell_volume                      733.12(13)
_cell_formula_units_Z             2
_cell_measurement_reflns_used     1976
_cell_measurement_temperature     200(2)
_cell_measurement_theta_max       23.681
_cell_measurement_theta_min       2.443
_shelx_estimated_absorpt_T_max    0.998
_shelx_estimated_absorpt_T_min    0.952
_exptl_absorpt_coefficient_mu     0.104
_exptl_absorpt_correction_T_max   0.8620
_exptl_absorpt_correction_T_min   0.7015
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1300 before and 0.0512 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1338 before and 0.0593 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
;
_exptl_crystal_colour             yellow
_exptl_crystal_colour_primary     yellow
_exptl_crystal_density_diffrn     1.369
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        plate
_exptl_crystal_F_000              316
_exptl_crystal_size_max           0.48
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.02
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.1034
_diffrn_reflns_av_unetI/netI      0.0804
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_h_min        -5
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_limit_l_min        0
_diffrn_reflns_number             2628
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full         25.230
_diffrn_reflns_theta_max          25.231
_diffrn_reflns_theta_min          2.276
_diffrn_ambient_temperature       200(2)
_diffrn_detector                  'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean  10.4
_diffrn_detector_type             'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device        'three-circle diffractometer'
_diffrn_measurement_device_type   'Bruker D8 QUEST'
_diffrn_measurement_method        'ω and φ scans'
_diffrn_radiation_monochromator   'mirror optics'
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'microfocus sealed X-ray tube'
_diffrn_source_type               'Incoatec I\ms'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 1850
_reflns_number_total              2628
_reflns_special_details
;
 _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.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection        'Bruker APEXII v2014.9-0 (Bruker, 2014)'
_computing_data_reduction         'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'XL (Sheldrick, 2008)'
_computing_structure_solution     'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max          0.227
_refine_diff_density_min          -0.218
_refine_diff_density_rms          0.053
_refine_ls_extinction_coef        0.030(4)
_refine_ls_extinction_expression  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref    1.146
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      207
_refine_ls_number_reflns          2628
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1037
_refine_ls_R_factor_gt            0.0545
_refine_ls_restrained_S_all       1.146
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+0.2911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0936
_refine_ls_wR_factor_ref          0.1103
_refine_special_details
;
 Refined as a 2-component twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6737(16) 0.3263(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens    mixed
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
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 0.2456(5) 0.04194(18) 0.59368(14) 0.0412(6) Uani 1 1 d . . . . .
 O2 O 0.3971(5) 0.2546(2) 0.79063(16) 0.0510(6) Uani 1 1 d . . . . .
 O3 O 0.0974(5) 0.1339(2) 0.87168(16) 0.0604(8) Uani 1 1 d . . . . .
 O4 O 0.8211(7) 0.5298(2) 0.0972(2) 0.0709(9) Uani 1 1 d . . . . .
 H4 H 0.917(13) 0.573(5) 0.038(4) 0.16(2) Uiso 1 1 d . . . . .
 O5 O 0.9473(6) 0.3647(2) 0.04368(17) 0.0587(7) Uani 1 1 d . . . . .
 N1 N 0.0153(5) 0.1970(2) 0.61864(16) 0.0334(6) Uani 1 1 d . . . . .
 N2 N 0.1255(5) 0.3125(2) 0.49540(17) 0.0326(6) Uani 1 1 d . . . . .
 C1 C 0.1744(6) 0.1347(3) 0.5694(2) 0.0321(7) Uani 1 1 d . . . . .
 C2 C 0.2395(6) 0.2085(2) 0.4864(2) 0.0295(7) Uani 1 1 d . . . . .
 C3 C 0.0016(6) 0.3028(3) 0.5732(2) 0.0333(7) Uani 1 1 d . . . . .
 C4 C -0.1409(7) 0.3932(3) 0.6126(2) 0.0430(8) Uani 1 1 d . . . . .
 H4A H -0.1235 0.4620 0.5720 0.064 Uiso 1 1 calc GR . . . .
 H4B H -0.0496 0.4200 0.6800 0.064 Uiso 1 1 calc GR . . . .
 H4C H -0.3443 0.3578 0.6120 0.064 Uiso 1 1 calc GR . . . .
 C5 C -0.0754(6) 0.1611(3) 0.7103(2) 0.0371(8) Uani 1 1 d . . . . .
 H5A H -0.1562 0.0736 0.7046 0.045 Uiso 1 1 calc R . . . .
 H5B H -0.2281 0.2030 0.7244 0.045 Uiso 1 1 calc R . . . .
 C6 C 0.1722(7) 0.1903(3) 0.7935(2) 0.0378(8) Uani 1 1 d . . . . .
 C7 C 0.3909(6) 0.1765(2) 0.4190(2) 0.0316(7) Uani 1 1 d . . . . .
 H7 H 0.4435 0.1010 0.4265 0.038 Uiso 1 1 calc R . . . .
 C8 C 0.4870(6) 0.2394(3) 0.33649(19) 0.0299(7) Uani 1 1 d . . . . .
 C9 C 0.4377(7) 0.3529(3) 0.3154(2) 0.0351(8) Uani 1 1 d . . . . .
 H9 H 0.3288 0.3908 0.3544 0.042 Uiso 1 1 calc R . . . .
 C10 C 0.5453(7) 0.4103(3) 0.2389(2) 0.0383(8) Uani 1 1 d . . . . .
 H10 H 0.5119 0.4879 0.2257 0.046 Uiso 1 1 calc R . . . .
 C11 C 0.7017(7) 0.3558(3) 0.1811(2) 0.0343(7) Uani 1 1 d . . . . .
 C12 C 0.7456(7) 0.2415(3) 0.1991(2) 0.0397(8) Uani 1 1 d . . . . .
 H12 H 0.8484 0.2027 0.1584 0.048 Uiso 1 1 calc R . . . .
 C13 C 0.6398(7) 0.1845(3) 0.2762(2) 0.0370(8) Uani 1 1 d . . . . .
 H13 H 0.6714 0.1065 0.2884 0.044 Uiso 1 1 calc R . . . .
 C14 C 0.8330(7) 0.4186(3) 0.1014(2) 0.0428(9) Uani 1 1 d . . . . .
 C15 C 0.3143(10) 0.1573(5) 0.9589(3) 0.0908(16) Uani 1 1 d . . . . .
 H15A H 0.4877 0.1317 0.9446 0.136 Uiso 1 1 calc GR . . . .
 H15B H 0.2406 0.1125 1.0121 0.136 Uiso 1 1 calc GR . . . .
 H15C H 0.3606 0.2434 0.9787 0.136 Uiso 1 1 calc GR . . . .


_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 1.221(3) . ?
 O2 C6 1.186(4) . ?
 O3 C6 1.336(4) . ?
 O3 C15 1.455(4) . ?
 O4 H4 1.09(6) . ?
 O4 C14 1.284(4) . ?
 O5 C14 1.239(4) . ?
 N1 C1 1.370(4) . ?
 N1 C3 1.392(3) . ?
 N1 C5 1.445(4) . ?
 N2 C2 1.410(4) . ?
 N2 C3 1.299(4) . ?
 C1 C2 1.483(4) . ?
 C2 C7 1.341(4) . ?
 C3 C4 1.474(4) . ?
 C4 H4A 0.9800 . ?
 C4 H4B 0.9800 . ?
 C4 H4C 0.9800 . ?
 C5 H5A 0.9900 . ?
 C5 H5B 0.9900 . ?
 C5 C6 1.508(4) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.454(4) . ?
 C8 C9 1.397(4) . ?
 C8 C13 1.393(4) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.376(4) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.381(4) . ?
 C11 C12 1.389(4) . ?
 C11 C14 1.485(4) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.375(4) . ?
 C13 H13 0.9500 . ?
 C15 H15A 0.9800 . ?
 C15 H15B 0.9800 . ?
 C15 H15C 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
 C6 O3 C15 115.3(3) . . ?
 C14 O4 H4 114(3) . . ?
 C1 N1 C3 108.2(2) . . ?
 C1 N1 C5 122.3(2) . . ?
 C3 N1 C5 128.8(2) . . ?
 C3 N2 C2 105.9(2) . . ?
 O1 C1 N1 125.5(3) . . ?
 O1 C1 C2 130.7(3) . . ?
 N1 C1 C2 103.8(2) . . ?
 N2 C2 C1 108.3(2) . . ?
 C7 C2 N2 129.3(2) . . ?
 C7 C2 C1 122.3(3) . . ?
 N1 C3 C4 121.4(3) . . ?
 N2 C3 N1 113.6(2) . . ?
 N2 C3 C4 124.9(3) . . ?
 C3 C4 H4A 109.5 . . ?
 C3 C4 H4B 109.5 . . ?
 C3 C4 H4C 109.5 . . ?
 H4A C4 H4B 109.5 . . ?
 H4A C4 H4C 109.5 . . ?
 H4B C4 H4C 109.5 . . ?
 N1 C5 H5A 109.4 . . ?
 N1 C5 H5B 109.4 . . ?
 N1 C5 C6 111.1(3) . . ?
 H5A C5 H5B 108.0 . . ?
 C6 C5 H5A 109.4 . . ?
 C6 C5 H5B 109.4 . . ?
 O2 C6 O3 125.2(3) . . ?
 O2 C6 C5 125.4(3) . . ?
 O3 C6 C5 109.4(3) . . ?
 C2 C7 H7 115.0 . . ?
 C2 C7 C8 130.0(3) . . ?
 C8 C7 H7 115.0 . . ?
 C9 C8 C7 123.3(3) . . ?
 C13 C8 C7 118.4(2) . . ?
 C13 C8 C9 118.3(3) . . ?
 C8 C9 H9 119.7 . . ?
 C10 C9 C8 120.7(3) . . ?
 C10 C9 H9 119.7 . . ?
 C9 C10 H10 119.8 . . ?
 C9 C10 C11 120.3(3) . . ?
 C11 C10 H10 119.8 . . ?
 C10 C11 C12 119.8(3) . . ?
 C10 C11 C14 121.3(3) . . ?
 C12 C11 C14 118.9(3) . . ?
 C11 C12 H12 120.1 . . ?
 C13 C12 C11 119.8(3) . . ?
 C13 C12 H12 120.1 . . ?
 C8 C13 H13 119.5 . . ?
 C12 C13 C8 121.1(3) . . ?
 C12 C13 H13 119.5 . . ?
 O4 C14 C11 116.1(3) . . ?
 O5 C14 O4 123.2(3) . . ?
 O5 C14 C11 120.6(3) . . ?
 O3 C15 H15A 109.5 . . ?
 O3 C15 H15B 109.5 . . ?
 O3 C15 H15C 109.5 . . ?
 H15A C15 H15B 109.5 . . ?
 H15A C15 H15C 109.5 . . ?
 H15B C15 H15C 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
 O1 C1 C2 N2 -175.3(3) . . . . ?
 O1 C1 C2 C7 2.8(5) . . . . ?
 N1 C1 C2 N2 2.9(3) . . . . ?
 N1 C1 C2 C7 -179.0(3) . . . . ?
 N1 C5 C6 O2 14.0(4) . . . . ?
 N1 C5 C6 O3 -166.8(3) . . . . ?
 N2 C2 C7 C8 1.1(5) . . . . ?
 C1 N1 C3 N2 3.3(3) . . . . ?
 C1 N1 C3 C4 -176.3(3) . . . . ?
 C1 N1 C5 C6 74.2(4) . . . . ?
 C1 C2 C7 C8 -176.5(3) . . . . ?
 C2 N2 C3 N1 -1.3(3) . . . . ?
 C2 N2 C3 C4 178.3(3) . . . . ?
 C2 C7 C8 C9 1.9(5) . . . . ?
 C2 C7 C8 C13 -179.1(3) . . . . ?
 C3 N1 C1 O1 174.7(3) . . . . ?
 C3 N1 C1 C2 -3.6(3) . . . . ?
 C3 N1 C5 C6 -95.3(3) . . . . ?
 C3 N2 C2 C1 -1.0(3) . . . . ?
 C3 N2 C2 C7 -178.9(3) . . . . ?
 C5 N1 C1 O1 3.3(5) . . . . ?
 C5 N1 C1 C2 -175.0(2) . . . . ?
 C5 N1 C3 N2 174.0(3) . . . . ?
 C5 N1 C3 C4 -5.7(5) . . . . ?
 C7 C8 C9 C10 177.0(3) . . . . ?
 C7 C8 C13 C12 -177.5(3) . . . . ?
 C8 C9 C10 C11 0.6(5) . . . . ?
 C9 C8 C13 C12 1.5(5) . . . . ?
 C9 C10 C11 C12 1.3(5) . . . . ?
 C9 C10 C11 C14 -176.7(3) . . . . ?
 C10 C11 C12 C13 -1.8(5) . . . . ?
 C10 C11 C14 O4 7.8(5) . . . . ?
 C10 C11 C14 O5 -172.5(3) . . . . ?
 C11 C12 C13 C8 0.4(5) . . . . ?
 C12 C11 C14 O4 -170.2(3) . . . . ?
 C12 C11 C14 O5 9.5(5) . . . . ?
 C13 C8 C9 C10 -2.0(4) . . . . ?
 C14 C11 C12 C13 176.3(3) . . . . ?
 C15 O3 C6 O2 1.0(5) . . . . ?
 C15 O3 C6 C5 -178.1(3) . . . . ?

_shelx_SHELXL_version_number      '2014/7'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
  _twin_individual_id
  _twin_individual_mass_fraction_refined
 1 0.6737(16)
 2 0.3263(16)

# start Validation Reply Form
_vrf_PLAT355_ead29twin
;
PROBLEM: Long    O-H (X0.82,N0.98A)  O4     -   H4     ..       1.08 Ang.  
RESPONSE: .Located and refined H position. Normal distance for a proton in a
carboxylic acid dimer with similar C-O distances.
;
