# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_rv186 #?# MeasurementCode


_audit_update_record             06-Jun-13

_chemical_name_common            ? #?# use for preliminary identification
_chemical_compound_source        ?
_chemical_absolute_configuration syn

_exptl_crystal_description       block #?# e.g.: needle, platelet; prisma
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.195 #?# in millimeters
_exptl_crystal_size_mid          0.127 #?# in millimeters
_exptl_crystal_size_min          0.051 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           ?
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      173(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    0.8_mm
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8Venture'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   11.8630(13)
_cell_length_b                   4.8437(7)
_cell_length_c                   12.6119(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.802(3)
_cell_angle_gamma                90.00
_cell_volume                     646.84(14)
_cell_measurement_temperature    173(2) #?# in K
_cell_measurement_reflns_used    112
_cell_measurement_theta_min      3.1702
_cell_measurement_theta_max      23.0265
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9043
_exptl_absorpt_correction_T_max  0.9580
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_diffrn_reflns_number            8079 #xl
_diffrn_reflns_av_R_equivalents  0.0407 #xl
_diffrn_reflns_av_sigmaI/netI    0.0390 #xl
_diffrn_reflns_limit_h_min       -14 #xl
_diffrn_reflns_limit_h_max       13 #xl
_diffrn_reflns_limit_k_min       -5 #xl
_diffrn_reflns_limit_k_max       5 #xl
_diffrn_reflns_limit_l_min       -15 #xl
_diffrn_reflns_limit_l_max       15 #xl
_diffrn_reflns_theta_min         3.18 #xl
_diffrn_reflns_theta_max         25.41 #xl
_diffrn_measured_fraction_theta_max 0.996 #xl
_diffrn_reflns_theta_full        25.34 #xl
_diffrn_measured_fraction_theta_full 0.996 #xl

_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'

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'

_reflns_number_total             2358 #xl
_reflns_number_gt                2117 #xl
_reflns_threshold_expression     >2sigma(I) #xl
_reflns_special_details          ?

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0376P)^2^+0.1254P] where P=(Fo^2^+2Fc^2^)/3' #xl
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed #?# mixed --> _refine_special_details
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       ? #xl
_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881' #xl
_refine_ls_abs_structure_Flack   1.7(11) #xl
_refine_ls_number_reflns         2358 #xl
_refine_ls_number_parameters     193 #xl
_refine_ls_number_restraints     1 #xl
_refine_ls_R_factor_all          0.0405 #xl
_refine_ls_R_factor_gt           0.0327 #xl
_refine_ls_wR_factor_ref         0.0809 #xl
_refine_ls_wR_factor_gt          0.0777 #xl
_refine_ls_goodness_of_fit_ref   1.059 #xl
_refine_ls_restrained_S_all      1.058 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.154 #xl
_refine_diff_density_min         -0.168 #xl
_refine_diff_density_rms         0.036 #xl

_refine_special_details          
;
C-bound H: constr
O-bound H: refall
;

_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;

_computing_structure_refinement  
;
Sheldrick, G. M. (2008).
<i>Acta Cryst.</i> A<b>64</b>, 112--122.
;

_computing_molecular_graphics    ?

_computing_publication_material  ?

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.18288(16) -0.2489(4) -0.06146(17) 0.0184(4) Uani 1 1 d . . .
H1 H 0.1410 -0.4323 -0.0698 0.022 Uiso 1 1 calc R . .
C2 C 0.09976(17) -0.0663(4) -0.16550(17) 0.0213(4) Uani 1 1 d . . .
H2A H 0.1165 0.1316 -0.1447 0.026 Uiso 1 1 calc R . .
H2B H 0.0092 -0.1045 -0.1913 0.026 Uiso 1 1 calc R . .
C3 C 0.13797(17) -0.1461(4) -0.26134(17) 0.0189(4) Uani 1 1 d . . .
H3A H 0.1178 0.0027 -0.3222 0.023 Uiso 1 1 calc R . .
C4 C 0.27978(17) -0.1867(4) -0.18862(16) 0.0173(4) Uani 1 1 d . . .
H4A H 0.3087 -0.3322 -0.2271 0.021 Uiso 1 1 calc R . .
C5 C 0.35627(17) 0.0712(4) -0.17378(17) 0.0225(4) Uani 1 1 d . . .
H5A H 0.3399 0.1460 -0.2525 0.027 Uiso 1 1 calc R . .
H5B H 0.3329 0.2135 -0.1309 0.027 Uiso 1 1 calc R . .
C6 C 0.32528(17) 0.2023(4) 0.21396(17) 0.0190(4) Uani 1 1 d . . .
C7 C 0.25656(17) 0.1185(4) 0.27381(16) 0.0195(4) Uani 1 1 d . . .
C8 C 0.16816(18) -0.0902(4) 0.22592(18) 0.0226(4) Uani 1 1 d . . .
H8 H 0.1221 -0.1497 0.2668 0.027 Uiso 1 1 calc R . .
C9 C 0.14592(18) -0.2136(4) 0.11923(17) 0.0223(4) Uani 1 1 d . . .
H9 H 0.0850 -0.3567 0.0877 0.027 Uiso 1 1 calc R . .
C10 C 0.21224(17) -0.1291(4) 0.05814(17) 0.0190(4) Uani 1 1 d . . .
C11 C 0.30248(17) 0.0756(4) 0.10726(16) 0.0202(4) Uani 1 1 d . . .
H11 H 0.3500 0.1309 0.0671 0.024 Uiso 1 1 calc R . .
C12 C 0.37178(19) 0.3935(5) 0.46086(19) 0.0314(5) Uani 1 1 d . . .
H12 H 0.4503 0.4209 0.4592 0.038 Uiso 1 1 calc R . .
C13 C 0.3395(2) 0.4907(5) 0.5449(2) 0.0373(6) Uani 1 1 d . . .
H13 H 0.3896 0.5991 0.6127 0.045 Uiso 1 1 calc R . .
C14 C 0.21722(19) 0.3964(5) 0.50957(18) 0.0300(5) Uani 1 1 d . . .
H14 H 0.1697 0.4323 0.5518 0.036 Uiso 1 1 calc R . .
N1 N 0.27212(14) 0.2513(4) 0.38036(14) 0.0213(4) Uani 1 1 d . . .
N2 N 0.17465(15) 0.2506(4) 0.41021(14) 0.0252(4) Uani 1 1 d . . .
O1 O 0.29786(11) -0.2849(3) -0.07393(11) 0.0207(3) Uani 1 1 d . . .
O2 O 0.08435(13) -0.4043(3) -0.31407(12) 0.0248(3) Uani 1 1 d . . .
H2 H 0.001(2) -0.384(6) -0.343(2) 0.042(7) Uiso 1 1 d . . .
O3 O 0.48738(13) -0.0001(3) -0.10733(13) 0.0287(4) Uani 1 1 d . . .
H3 H 0.530(2) 0.131(6) -0.053(2) 0.043(7) Uiso 1 1 d . . .
O4 O 0.41339(13) 0.4060(3) 0.26075(13) 0.0260(3) Uani 1 1 d . . .
H4 H 0.442(3) 0.438(6) 0.205(3) 0.060(9) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0175(9) 0.0172(9) 0.0249(10) -0.0032(8) 0.0133(8) -0.0012(8)
C2 0.0186(9) 0.0220(11) 0.0243(10) -0.0047(9) 0.0104(8) 0.0023(8)
C3 0.0165(9) 0.0187(10) 0.0197(10) -0.0010(8) 0.0065(7) 0.0020(8)
C4 0.0182(9) 0.0179(10) 0.0164(9) 0.0015(8) 0.0083(8) 0.0047(8)
C5 0.0225(10) 0.0234(10) 0.0237(10) 0.0013(9) 0.0122(8) 0.0011(9)
C6 0.0146(9) 0.0194(10) 0.0214(10) 0.0022(8) 0.0068(8) 0.0010(8)
C7 0.0190(9) 0.0226(10) 0.0158(9) 0.0007(9) 0.0070(8) 0.0039(8)
C8 0.0224(10) 0.0270(11) 0.0247(10) 0.0011(9) 0.0161(8) -0.0015(9)
C9 0.0239(10) 0.0220(11) 0.0257(11) -0.0025(9) 0.0154(9) -0.0046(9)
C10 0.0190(9) 0.0181(10) 0.0211(10) 0.0017(8) 0.0102(8) 0.0026(8)
C11 0.0193(9) 0.0241(10) 0.0218(10) 0.0027(9) 0.0132(8) 0.0017(9)
C12 0.0226(10) 0.0468(14) 0.0253(11) -0.0100(10) 0.0112(9) -0.0092(10)
C13 0.0345(12) 0.0542(16) 0.0248(12) -0.0161(11) 0.0148(10) -0.0149(12)
C14 0.0298(11) 0.0425(13) 0.0203(11) -0.0069(10) 0.0136(9) 0.0007(10)
N1 0.0164(8) 0.0296(10) 0.0182(8) -0.0016(7) 0.0082(7) -0.0001(7)
N2 0.0200(8) 0.0378(10) 0.0214(9) -0.0010(8) 0.0126(7) 0.0010(8)
O1 0.0190(6) 0.0275(8) 0.0189(7) 0.0038(6) 0.0114(6) 0.0064(6)
O2 0.0191(7) 0.0281(7) 0.0274(8) -0.0104(7) 0.0108(6) -0.0030(7)
O3 0.0179(7) 0.0334(9) 0.0321(8) -0.0100(7) 0.0089(6) -0.0025(6)
O4 0.0236(7) 0.0315(8) 0.0241(8) -0.0067(7) 0.0119(6) -0.0112(7)

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 O1 1.452(2) . ?
C1 C10 1.503(3) . ?
C1 C2 1.520(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.520(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O2 1.424(2) . ?
C3 C4 1.523(2) . ?
C3 H3A 1.0000 . ?
C4 O1 1.444(2) . ?
C4 C5 1.505(3) . ?
C4 H4A 1.0000 . ?
C5 O3 1.437(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O4 1.363(2) . ?
C6 C11 1.390(3) . ?
C6 C7 1.398(3) . ?
C7 C8 1.384(3) . ?
C7 N1 1.425(2) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?
C12 N1 1.349(3) . ?
C12 C13 1.363(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 N2 1.324(3) . ?
C14 H14 0.9500 . ?
N1 N2 1.368(2) . ?
O2 H2 0.89(3) . ?
O3 H3 0.90(3) . ?
O4 H4 0.92(3) . ?

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
O1 C1 C10 110.56(14) . . ?
O1 C1 C2 104.59(14) . . ?
C10 C1 C2 114.11(16) . . ?
O1 C1 H1 109.1 . . ?
C10 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
C1 C2 C3 103.21(14) . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
O2 C3 C2 111.36(15) . . ?
O2 C3 C4 107.91(14) . . ?
C2 C3 C4 101.45(15) . . ?
O2 C3 H3A 111.9 . . ?
C2 C3 H3A 111.9 . . ?
C4 C3 H3A 111.9 . . ?
O1 C4 C5 109.88(14) . . ?
O1 C4 C3 105.70(14) . . ?
C5 C4 C3 114.10(15) . . ?
O1 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
O3 C5 C4 107.85(16) . . ?
O3 C5 H5A 110.1 . . ?
C4 C5 H5A 110.1 . . ?
O3 C5 H5B 110.1 . . ?
C4 C5 H5B 110.1 . . ?
H5A C5 H5B 108.5 . . ?
O4 C6 C11 121.00(16) . . ?
O4 C6 C7 119.76(17) . . ?
C11 C6 C7 119.24(17) . . ?
C8 C7 C6 119.21(17) . . ?
C8 C7 N1 119.45(17) . . ?
C6 C7 N1 121.28(18) . . ?
C7 C8 C9 120.94(17) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C10 120.33(18) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 118.71(17) . . ?
C11 C10 C1 120.54(16) . . ?
C9 C10 C1 120.70(17) . . ?
C10 C11 C6 121.54(16) . . ?
C10 C11 H11 119.2 . . ?
C6 C11 H11 119.2 . . ?
N1 C12 C13 107.66(18) . . ?
N1 C12 H12 126.2 . . ?
C13 C12 H12 126.2 . . ?
C12 C13 C14 104.84(19) . . ?
C12 C13 H13 127.6 . . ?
C14 C13 H13 127.6 . . ?
N2 C14 C13 112.11(18) . . ?
N2 C14 H14 123.9 . . ?
C13 C14 H14 123.9 . . ?
C12 N1 N2 110.90(16) . . ?
C12 N1 C7 129.57(16) . . ?
N2 N1 C7 119.50(15) . . ?
C14 N2 N1 104.48(16) . . ?
C4 O1 C1 110.26(14) . . ?
C3 O2 H2 106.1(18) . . ?
C5 O3 H3 111.3(16) . . ?
C6 O4 H4 105.2(18) . . ?

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 C3 31.22(18) . . . . ?
C10 C1 C2 C3 152.15(15) . . . . ?
C1 C2 C3 O2 76.50(18) . . . . ?
C1 C2 C3 C4 -38.09(18) . . . . ?
O2 C3 C4 O1 -85.53(17) . . . . ?
C2 C3 C4 O1 31.60(18) . . . . ?
O2 C3 C4 C5 153.63(15) . . . . ?
C2 C3 C4 C5 -89.25(18) . . . . ?
O1 C4 C5 O3 63.42(18) . . . . ?
C3 C4 C5 O3 -178.09(15) . . . . ?
O4 C6 C7 C8 -179.43(17) . . . . ?
C11 C6 C7 C8 0.5(3) . . . . ?
O4 C6 C7 N1 3.2(3) . . . . ?
C11 C6 C7 N1 -176.88(17) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
N1 C7 C8 C9 176.57(18) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 1.4(3) . . . . ?
C8 C9 C10 C1 -176.03(18) . . . . ?
O1 C1 C10 C11 39.9(2) . . . . ?
C2 C1 C10 C11 -77.6(2) . . . . ?
O1 C1 C10 C9 -142.71(17) . . . . ?
C2 C1 C10 C9 99.7(2) . . . . ?
C9 C10 C11 C6 -1.8(3) . . . . ?
C1 C10 C11 C6 175.66(17) . . . . ?
O4 C6 C11 C10 -179.23(18) . . . . ?
C7 C6 C11 C10 0.8(3) . . . . ?
N1 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 N2 -0.2(3) . . . . ?
C13 C12 N1 N2 -0.5(3) . . . . ?
C13 C12 N1 C7 177.5(2) . . . . ?
C8 C7 N1 C12 158.0(2) . . . . ?
C6 C7 N1 C12 -24.6(3) . . . . ?
C8 C7 N1 N2 -24.1(3) . . . . ?
C6 C7 N1 N2 153.35(18) . . . . ?
C13 C14 N2 N1 -0.1(3) . . . . ?
C12 N1 N2 C14 0.4(2) . . . . ?
C7 N1 N2 C14 -177.86(18) . . . . ?
C5 C4 O1 C1 110.72(16) . . . . ?
C3 C4 O1 C1 -12.83(18) . . . . ?
C10 C1 O1 C4 -134.81(15) . . . . ?
C2 C1 O1 C4 -11.56(18) . . . . ?

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
_geom_hbond_publ_flag
O2 H2 N2 0.89(3) 1.98(3) 2.848(2) 167(3) 2_545 ?
O3 H3 O1 0.90(3) 1.99(3) 2.7478(19) 141(2) 2_655 ?
O4 H4 O3 0.92(3) 1.80(3) 2.719(2) 174(3) 2_655 ?

_audit_block_code                C14H16N2O4_rv186_carell
_audit_creation_method           'form98_non/compatible with shelxl97-2'

_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 N2 O4'
_chemical_formula_sum            'C14 H16 N2 O4'
_chemical_formula_weight         276.288
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            2 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.4186(3)
_exptl_crystal_F_000             292

_database_code_depnum_ccdc_archive 'CCDC 965412'