# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_wwc-1
_database_code_depnum_ccdc_archive 'CCDC 1892780'
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H12 N2 O2'
_chemical_formula_weight         180.21

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.090(3)
_cell_length_b                   10.916(4)
_cell_length_c                   10.931(4)
_cell_angle_alpha                60.934(4)
_cell_angle_beta                 63.573(4)
_cell_angle_gamma                73.550(4)
_cell_volume                     939.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1607
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      25.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5229
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3738
_reflns_number_gt                2592
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0921P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3738
_refine_ls_number_parameters     239
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1764
_refine_ls_wR_factor_gt          0.1532
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      4.480
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.9056(7) 0.8443(7) 0.2355(7) 0.0464(17) Uani 1 1 d . . .
O4 O 1.0518(7) 0.6791(6) 0.6376(7) 0.0586(18) Uani 1 1 d . . .
O2 O 0.4620(6) 0.2771(6) 1.0893(7) 0.0583(17) Uani 1 1 d . . .
N1 N 0.6282(7) 0.1169(6) 0.7177(7) 0.0440(17) Uani 1 1 d . . .
O3 O 1.1925(7) 0.5672(7) 0.4909(8) 0.070(2) Uani 1 1 d . . .
O1 O 0.3205(8) 0.3767(8) 0.9509(8) 0.078(2) Uani 1 1 d . . .
N2 N 0.7443(9) 0.0074(8) 0.5660(9) 0.067(2) Uani 1 1 d . . .
C6 C 0.4217(9) 0.2952(9) 0.9795(10) 0.052(2) Uani 1 1 d . . .
C1 C 0.7391(9) 0.0254(8) 0.7660(9) 0.049(2) Uani 1 1 d . . .
H1 H 0.7623 0.0101 0.8460 0.058 Uiso 1 1 calc RD . .
C13 C 1.0042(8) 0.7469(8) 0.3054(9) 0.0440(19) Uani 1 1 d . . .
C5 C 0.5187(9) 0.2021(9) 0.9067(9) 0.048(2) Uani 1 1 d . . .
H5 H 0.5787 0.1311 0.9547 0.057 Uiso 1 1 calc R . .
N4 N 0.7956(9) 0.9633(9) 0.0676(9) 0.065(2) Uani 1 1 d . . .
C14 C 0.9952(9) 0.7403(9) 0.4339(9) 0.050(2) Uani 1 1 d . . .
H14 H 0.9194 0.7975 0.4741 0.060 Uiso 1 1 calc R . .
C4 C 0.5274(8) 0.2114(8) 0.7768(9) 0.0441(19) Uani 1 1 d . . .
C15 C 1.0922(9) 0.6524(8) 0.5179(9) 0.049(2) Uani 1 1 d . . .
C3 C 0.6379(11) 0.0995(10) 0.5981(10) 0.061(2) Uani 1 1 d . . .
H3 H 0.5746 0.1488 0.5451 0.073 Uiso 1 1 calc R . .
C10 C 0.8044(10) 0.9437(9) 0.2803(10) 0.055(2) Uani 1 1 d . . .
H10 H 0.7845 0.9599 0.3631 0.066 Uiso 1 1 calc R . .
C12 C 0.8947(11) 0.8636(10) 0.1063(10) 0.059(2) Uani 1 1 d . . .
H12 H 0.9527 0.8104 0.0520 0.070 Uiso 1 1 calc R . .
C2 C 0.8066(11) -0.0371(9) 0.6685(11) 0.061(2) Uani 1 1 d . . .
H2 H 0.8876 -0.1038 0.6724 0.073 Uiso 1 1 calc RD . .
C18 C 1.1136(11) 0.6614(10) 0.2248(11) 0.062(3) Uani 1 1 d . . .
H18A H 1.1759 0.5996 0.2805 0.094 Uiso 1 1 calc R . .
H18B H 1.1737 0.7227 0.1265 0.094 Uiso 1 1 calc R . .
H18C H 1.0618 0.6068 0.2156 0.094 Uiso 1 1 calc R . .
C16 C 1.1389(10) 0.6066(9) 0.7320(10) 0.057(2) Uani 1 1 d . . .
H16A H 1.2436 0.6173 0.6714 0.069 Uiso 1 1 calc R . .
H16B H 1.1241 0.5071 0.7854 0.069 Uiso 1 1 calc R . .
C9 C 0.4432(11) 0.3178(10) 0.6821(11) 0.066(3) Uani 1 1 d . . .
H9A H 0.3824 0.3814 0.7270 0.100 Uiso 1 1 calc R . .
H9B H 0.3813 0.2715 0.6743 0.100 Uiso 1 1 calc R . .
H9C H 0.5115 0.3694 0.5835 0.100 Uiso 1 1 calc R . .
C7 C 0.3714(11) 0.3585(10) 1.1762(11) 0.064(3) Uani 1 1 d . . .
H7A H 0.2689 0.3359 1.2239 0.077 Uiso 1 1 calc R . .
H7B H 0.3746 0.4583 1.1111 0.077 Uiso 1 1 calc R . .
C17 C 1.0887(12) 0.6702(11) 0.8409(12) 0.072(3) Uani 1 1 d . . .
H17A H 1.1085 0.7675 0.7871 0.108 Uiso 1 1 calc R . .
H17B H 1.1413 0.6211 0.9087 0.108 Uiso 1 1 calc R . .
H17C H 0.9840 0.6631 0.8969 0.108 Uiso 1 1 calc R . .
C11 C 0.7397(11) 1.0133(10) 0.1735(10) 0.062(2) Uani 1 1 d . . .
H11 H 0.6656 1.0868 0.1744 0.074 Uiso 1 1 calc R . .
C8 C 0.4324(13) 0.3221(13) 1.2924(14) 0.084(3) Uani 1 1 d . . .
H8A H 0.4276 0.2233 1.3569 0.126 Uiso 1 1 calc R . .
H8B H 0.3752 0.3751 1.3510 0.126 Uiso 1 1 calc R . .
H8C H 0.5340 0.3442 1.2440 0.126 Uiso 1 1 calc R . .


_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
N3 C12 1.373(10) . ?
N3 C10 1.380(10) . ?
N3 C13 1.411(10) . ?
O4 C15 1.338(9) . ?
O4 C16 1.443(10) . ?
O2 C6 1.343(10) . ?
O2 C7 1.454(9) . ?
N1 C3 1.368(10) . ?
N1 C1 1.382(10) . ?
N1 C4 1.409(9) . ?
O3 C15 1.202(9) . ?
O1 C6 1.196(10) . ?
N2 C3 1.297(11) . ?
N2 C2 1.346(12) . ?
C6 C5 1.467(10) . ?
C1 C2 1.365(11) . ?
C13 C14 1.333(11) . ?
C13 C18 1.488(10) . ?
C5 C4 1.337(11) . ?
N4 C12 1.295(11) . ?
N4 C11 1.347(11) . ?
C14 C15 1.461(12) . ?
C4 C9 1.483(11) . ?
C10 C11 1.379(12) . ?
C16 C17 1.491(12) . ?
C7 C8 1.489(15) . ?

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
C12 N3 C10 106.0(7) . . ?
C12 N3 C13 127.3(7) . . ?
C10 N3 C13 126.6(7) . . ?
C15 O4 C16 117.5(6) . . ?
C6 O2 C7 116.1(6) . . ?
C3 N1 C1 106.1(7) . . ?
C3 N1 C4 126.7(7) . . ?
C1 N1 C4 127.2(6) . . ?
C3 N2 C2 103.8(7) . . ?
O1 C6 O2 122.4(7) . . ?
O1 C6 C5 127.9(8) . . ?
O2 C6 C5 109.7(7) . . ?
C2 C1 N1 103.5(7) . . ?
C14 C13 N3 118.8(7) . . ?
C14 C13 C18 125.4(8) . . ?
N3 C13 C18 115.8(7) . . ?
C4 C5 C6 125.1(8) . . ?
C12 N4 C11 104.3(7) . . ?
C13 C14 C15 126.7(7) . . ?
C5 C4 N1 119.2(7) . . ?
C5 C4 C9 125.8(7) . . ?
N1 C4 C9 114.9(7) . . ?
O3 C15 O4 122.7(8) . . ?
O3 C15 C14 128.2(8) . . ?
O4 C15 C14 109.0(6) . . ?
N2 C3 N1 113.2(8) . . ?
C11 C10 N3 103.7(7) . . ?
N4 C12 N3 113.2(7) . . ?
C1 C2 N2 113.4(8) . . ?
O4 C16 C17 107.4(7) . . ?
O2 C7 C8 107.7(8) . . ?
C10 C11 N4 112.7(8) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.058
