# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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#######################################################################

data_mo_hol86_0m
_database_code_depnum_ccdc_archive 'CCDC 1534878'
_audit_update_record             
;
2017-02-27 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 N2 O2, H2 O'
_chemical_formula_sum            'C14 H12 N2 O3'
_chemical_formula_weight         256.26

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.1026(3)
_cell_length_b                   7.8866(3)
_cell_length_c                   11.4159(5)
_cell_angle_alpha                92.777(2)
_cell_angle_beta                 92.263(2)
_cell_angle_gamma                114.9680(10)
_cell_volume                     577.75(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      45.35

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.372
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.146
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'SADABS-2014/5, Bruker, Madison, 2014'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microfocus source'
_diffrn_measurement_device_type  
'BRUKER D8 Venture, Bruker Photon 100 CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52988
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.856
_diffrn_reflns_theta_max         34.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5048
_reflns_number_gt                4143
_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       'APEX3 v2015.5-2'
_computing_cell_refinement       'APEX3 v2014.5-2'
_computing_data_reduction        'APEX3 v2014.5-2'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 4.3'

_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)+(0.0691P)²+0.0836P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5048
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.74409(9) 0.78889(7) 0.37251(5) 0.01393(11) Uani 1 1 d . . . . .
O2 O 0.72866(10) 0.17494(8) 0.56792(5) 0.01627(12) Uani 1 1 d . . . . .
O3 O 0.46495(11) 0.21827(9) -0.09024(5) 0.02266(15) Uani 1 1 d . . . . .
N2 N 0.62336(10) 0.15629(9) 0.20532(5) 0.01229(12) Uani 1 1 d . . . . .
N1 N 0.62407(10) 0.30903(9) 0.15641(5) 0.01239(12) Uani 1 1 d . . . . .
C6 C 0.78408(10) 0.65194(9) 0.54719(5) 0.00790(11) Uani 1 1 d . . . . .
C3 C 0.69695(10) 0.31863(9) 0.39628(6) 0.00834(11) Uani 1 1 d . . . . .
C2 C 0.70120(10) 0.47602(9) 0.34626(6) 0.00792(11) Uani 1 1 d . . . . .
C5 C 0.74431(10) 0.65266(9) 0.41883(6) 0.00850(12) Uani 1 1 d . . . . .
C7 C 0.77323(10) 0.48961(9) 0.59846(6) 0.00829(11) Uani 1 1 d . . . . .
C9 C 0.82908(10) 0.81481(9) 0.61857(6) 0.00980(12) Uani 1 1 d . . . . .
C1 C 0.66139(11) 0.46374(9) 0.22391(6) 0.01039(12) Uani 1 1 d . . . . .
C12 C 0.80401(11) 0.49340(10) 0.72038(6) 0.01002(12) Uani 1 1 d . . . . .
C4 C 0.65750(11) 0.15964(9) 0.32088(6) 0.01047(12) Uani 1 1 d . . . . .
C8 C 0.73206(10) 0.31567(9) 0.52605(6) 0.00911(12) Uani 1 1 d . . . . .
C11 C 0.84899(11) 0.65538(10) 0.79181(6) 0.01034(12) Uani 1 1 d . . . . .
C10 C 0.86253(10) 0.81943(9) 0.74015(6) 0.01017(12) Uani 1 1 d . . . . .
C14 C 0.88295(13) 0.65539(11) 0.92260(6) 0.01523(14) Uani 1 1 d . . . . .
C13 C 0.91200(12) 0.99676(10) 0.81520(7) 0.01466(14) Uani 1 1 d . . . . .
H12 H 0.789(2) 0.3784(18) 0.7544(12) 0.026(3) Uiso 1 1 d . . . . .
H1 H 0.650(2) 0.5610(18) 0.1836(12) 0.024(3) Uiso 1 1 d . . . . .
H9 H 0.836(2) 0.9257(19) 0.5851(12) 0.030(3) Uiso 1 1 d . . . . .
H4 H 0.654(2) 0.0445(19) 0.3519(12) 0.027(3) Uiso 1 1 d . . . . .
H14A H 0.7835(19) 0.6920(18) 0.9629(11) 0.024(3) Uiso 1 1 d . . . . .
H13A H 0.817(2) 0.9729(18) 0.8816(11) 0.026(3) Uiso 1 1 d . . . . .
H13B H 1.054(2) 1.0466(18) 0.8489(12) 0.027(3) Uiso 1 1 d . . . . .
H14B H 0.861(2) 0.5288(19) 0.9434(12) 0.032(3) Uiso 1 1 d . . . . .
H13C H 0.897(2) 1.0897(19) 0.7673(12) 0.028(3) Uiso 1 1 d . . . . .
H3A H 0.515(2) 0.236(2) -0.0217(15) 0.043(4) Uiso 1 1 d . . . . .
H14C H 1.023(2) 0.7427(19) 0.9465(12) 0.029(3) Uiso 1 1 d . . . . .
H3B H 0.448(2) 0.107(2) -0.1115(14) 0.042(4) 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 C5 1.2207(8) . ?
O2 C8 1.2209(8) . ?
O3 H3A 0.827(17) . ?
O3 H3B 0.851(16) . ?
N2 C4 1.3288(9) . ?
N2 N1 1.3502(9) . ?
N1 C1 1.3313(9) . ?
C6 C9 1.3955(9) . ?
C6 C7 1.4073(9) . ?
C6 C5 1.4821(9) . ?
C3 C2 1.3807(9) . ?
C3 C4 1.4041(9) . ?
C3 C8 1.4955(9) . ?
C2 C1 1.4045(9) . ?
C2 C5 1.4929(9) . ?
C7 C12 1.3971(9) . ?
C7 C8 1.4775(9) . ?
C9 C10 1.3949(9) . ?
C9 H9 0.955(14) . ?
C1 H1 0.945(13) . ?
C12 C11 1.3904(10) . ?
C12 H12 0.969(13) . ?
C4 H4 0.981(13) . ?
C11 C10 1.4157(10) . ?
C11 C14 1.5031(10) . ?
C10 C13 1.5029(10) . ?
C14 H14A 0.989(13) . ?
C14 H14B 0.986(14) . ?
C14 H14C 0.960(14) . ?
C13 H13A 1.006(13) . ?
C13 H13B 0.970(13) . ?
C13 H13C 0.973(13) . ?

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
H3A O3 H3B 104.6(15) . . ?
C4 N2 N1 120.03(6) . . ?
C1 N1 N2 119.94(6) . . ?
C9 C6 C7 119.54(6) . . ?
C9 C6 C5 119.11(6) . . ?
C7 C6 C5 121.34(6) . . ?
C2 C3 C4 117.62(6) . . ?
C2 C3 C8 121.66(6) . . ?
C4 C3 C8 120.72(6) . . ?
C3 C2 C1 117.48(6) . . ?
C3 C2 C5 121.66(6) . . ?
C1 C2 C5 120.86(6) . . ?
O1 C5 C6 122.79(6) . . ?
O1 C5 C2 120.29(6) . . ?
C6 C5 C2 116.91(5) . . ?
C12 C7 C6 119.34(6) . . ?
C12 C7 C8 119.24(6) . . ?
C6 C7 C8 121.42(6) . . ?
C10 C9 C6 121.15(6) . . ?
C10 C9 H9 118.3(8) . . ?
C6 C9 H9 120.5(8) . . ?
N1 C1 C2 122.46(6) . . ?
N1 C1 H1 114.5(8) . . ?
C2 C1 H1 122.9(8) . . ?
C11 C12 C7 121.30(6) . . ?
C11 C12 H12 120.6(8) . . ?
C7 C12 H12 118.1(8) . . ?
N2 C4 C3 122.45(6) . . ?
N2 C4 H4 116.7(8) . . ?
C3 C4 H4 120.9(8) . . ?
O2 C8 C7 122.74(6) . . ?
O2 C8 C3 120.31(6) . . ?
C7 C8 C3 116.94(6) . . ?
C12 C11 C10 119.39(6) . . ?
C12 C11 C14 120.02(6) . . ?
C10 C11 C14 120.58(6) . . ?
C9 C10 C11 119.27(6) . . ?
C9 C10 C13 120.22(6) . . ?
C11 C10 C13 120.52(6) . . ?
C11 C14 H14A 109.8(7) . . ?
C11 C14 H14B 109.6(8) . . ?
H14A C14 H14B 109.1(11) . . ?
C11 C14 H14C 108.9(8) . . ?
H14A C14 H14C 110.0(11) . . ?
H14B C14 H14C 109.5(11) . . ?
C10 C13 H13A 111.1(7) . . ?
C10 C13 H13B 110.0(8) . . ?
H13A C13 H13B 108.0(11) . . ?
C10 C13 H13C 109.6(8) . . ?
H13A C13 H13C 109.4(10) . . ?
H13B C13 H13C 108.7(11) . . ?

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
C4 N2 N1 C1 0.77(10) . . . . ?
C4 C3 C2 C1 1.30(10) . . . . ?
C8 C3 C2 C1 -178.47(6) . . . . ?
C4 C3 C2 C5 -179.27(6) . . . . ?
C8 C3 C2 C5 0.96(10) . . . . ?
C9 C6 C5 O1 -1.85(10) . . . . ?
C7 C6 C5 O1 176.87(6) . . . . ?
C9 C6 C5 C2 178.79(6) . . . . ?
C7 C6 C5 C2 -2.49(9) . . . . ?
C3 C2 C5 O1 -178.91(6) . . . . ?
C1 C2 C5 O1 0.50(10) . . . . ?
C3 C2 C5 C6 0.47(10) . . . . ?
C1 C2 C5 C6 179.87(6) . . . . ?
C9 C6 C7 C12 1.16(10) . . . . ?
C5 C6 C7 C12 -177.55(6) . . . . ?
C9 C6 C7 C8 -178.21(6) . . . . ?
C5 C6 C7 C8 3.07(10) . . . . ?
C7 C6 C9 C10 -0.34(10) . . . . ?
C5 C6 C9 C10 178.40(6) . . . . ?
N2 N1 C1 C2 0.09(11) . . . . ?
C3 C2 C1 N1 -1.14(11) . . . . ?
C5 C2 C1 N1 179.43(6) . . . . ?
C6 C7 C12 C11 -1.22(10) . . . . ?
C8 C7 C12 C11 178.17(6) . . . . ?
N1 N2 C4 C3 -0.56(11) . . . . ?
C2 C3 C4 N2 -0.51(10) . . . . ?
C8 C3 C4 N2 179.26(6) . . . . ?
C12 C7 C8 O2 -1.86(11) . . . . ?
C6 C7 C8 O2 177.52(7) . . . . ?
C12 C7 C8 C3 179.06(6) . . . . ?
C6 C7 C8 C3 -1.57(10) . . . . ?
C2 C3 C8 O2 -179.57(6) . . . . ?
C4 C3 C8 O2 0.67(10) . . . . ?
C2 C3 C8 C7 -0.46(10) . . . . ?
C4 C3 C8 C7 179.78(6) . . . . ?
C7 C12 C11 C10 0.42(11) . . . . ?
C7 C12 C11 C14 -179.52(6) . . . . ?
C6 C9 C10 C11 -0.45(10) . . . . ?
C6 C9 C10 C13 179.65(6) . . . . ?
C12 C11 C10 C9 0.41(10) . . . . ?
C14 C11 C10 C9 -179.64(6) . . . . ?
C12 C11 C10 C13 -179.69(6) . . . . ?
C14 C11 C10 C13 0.26(11) . . . . ?

_refine_diff_density_max         0.614
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.074

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
