# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_mtg_2m
_database_code_depnum_ccdc_archive 'CCDC 1811947'
_audit_update_record             
;
2017-12-18 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;

_audit_creation_date             2016-10-20T16:29:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H14 N2 O1'
_chemical_formula_sum            'C12 H14 N2 O'
_chemical_formula_weight         202.25
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8293(3)
_cell_length_b                   9.3602(5)
_cell_length_c                   10.5304(6)
_cell_angle_alpha                77.9070(10)
_cell_angle_beta                 80.1830(10)
_cell_angle_gamma                78.0310(10)
_cell_volume                     544.74(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4063
_cell_measurement_theta_min      2
_cell_measurement_theta_max      30
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       tabular
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             216
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_measurement_device_type  'Bruker-Axs Smart-Apex CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.333
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_number            10502
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_full        30.08
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             3185
_reflns_number_gt                2586
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0823P)²+0.0437P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.057(11)
_refine_ls_number_reflns         3185
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.46954(19) 0.10399(11) 0.26819(9) 0.0414(2) Uani 1 1 d . . .
C2 C 0.6094(2) 0.15660(13) 0.33496(11) 0.0501(3) Uani 1 1 d . . .
C3 C 0.7187(3) 0.27530(13) 0.26805(13) 0.0572(3) Uani 1 1 d . . .
C4 C 0.6878(3) 0.34138(14) 0.14000(13) 0.0592(3) Uani 1 1 d . . .
C5 C 0.5435(2) 0.29040(13) 0.07424(12) 0.0538(3) Uani 1 1 d . . .
C6 C 0.43569(19) 0.17232(11) 0.13937(10) 0.0430(2) Uani 1 1 d . . .
C7 C 0.28654(19) 0.08698(11) 0.09848(10) 0.0434(2) Uani 1 1 d . . .
C8 C 0.25172(18) -0.03455(11) 0.22001(9) 0.0413(2) Uani 1 1 d . . .
C9 C 0.09040(18) -0.26878(12) 0.31580(10) 0.0442(2) Uani 1 1 d . . .
C10 C -0.0217(3) -0.36541(17) 0.25349(15) 0.0644(4) Uani 1 1 d . . .
C11 C 0.3238(2) -0.35591(14) 0.35986(15) 0.0568(3) Uani 1 1 d . . .
C12 C -0.0772(2) -0.21661(16) 0.43110(13) 0.0578(3) Uani 1 1 d . . .
N1 N 0.35415(17) -0.02088(10) 0.31655(8) 0.0452(2) Uani 1 1 d . . .
N2 N 0.13360(17) -0.13935(11) 0.21290(9) 0.0469(2) Uani 1 1 d . . .
O1 O 0.20999(17) 0.09980(11) -0.00368(8) 0.0614(3) Uani 1 1 d . . .
H2 H 0.634(3) 0.1141(17) 0.4250(16) 0.063(4) Uiso 1 1 d . . .
H3 H 0.817(3) 0.312(2) 0.3174(16) 0.075(5) Uiso 1 1 d . . .
H4 H 0.770(3) 0.425(2) 0.0975(17) 0.079(5) Uiso 1 1 d . . .
H5 H 0.515(3) 0.3349(18) -0.0139(17) 0.067(4) Uiso 1 1 d . . .
H10A H -0.064(3) -0.453(2) 0.322(2) 0.091(6) Uiso 1 1 d . . .
H10B H 0.087(4) -0.399(2) 0.181(2) 0.097(6) Uiso 1 1 d . . .
H10C H -0.168(4) -0.313(2) 0.2169(18) 0.086(5) Uiso 1 1 d . . .
H11A H 0.291(3) -0.449(2) 0.4283(18) 0.078(5) Uiso 1 1 d . . .
H11B H 0.405(3) -0.296(2) 0.4025(16) 0.073(5) Uiso 1 1 d . . .
H11C H 0.432(3) -0.385(2) 0.2830(18) 0.080(5) Uiso 1 1 d . . .
H12A H -0.105(3) -0.309(2) 0.5005(18) 0.080(5) Uiso 1 1 d . . .
H12B H -0.011(3) -0.150(2) 0.4671(18) 0.080(5) Uiso 1 1 d . . .
H12C H -0.229(3) -0.167(2) 0.4008(18) 0.079(5) Uiso 1 1 d . . .
H21 H 0.065(3) -0.1271(18) 0.1407(16) 0.061(4) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.3816(14) . ?
C1 C6 1.4013(14) . ?
C1 N1 1.4274(12) . ?
C2 C3 1.3961(16) . ?
C3 C4 1.3857(19) . ?
C4 C5 1.3851(18) . ?
C5 C6 1.3822(15) . ?
C6 C7 1.4626(14) . ?
C7 O1 1.2075(13) . ?
C7 C8 1.5395(14) . ?
C8 N1 1.3037(12) . ?
C8 N2 1.3306(13) . ?
C9 N2 1.4794(13) . ?
C9 C12 1.5210(17) . ?
C9 C10 1.5218(15) . ?
C9 C11 1.5257(16) . ?

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
C2 C1 C6 120.06(9) . . ?
C2 C1 N1 126.09(9) . . ?
C6 C1 N1 113.83(8) . . ?
C1 C2 C3 117.59(10) . . ?
C4 C3 C2 122.27(11) . . ?
C5 C4 C3 119.99(11) . . ?
C6 C5 C4 118.18(11) . . ?
C5 C6 C1 121.88(10) . . ?
C5 C6 C7 132.54(10) . . ?
C1 C6 C7 105.48(8) . . ?
O1 C7 C6 131.44(10) . . ?
O1 C7 C8 126.05(10) . . ?
C6 C7 C8 102.48(8) . . ?
N1 C8 N2 128.95(10) . . ?
N1 C8 C7 112.72(9) . . ?
N2 C8 C7 118.29(9) . . ?
N2 C9 C12 109.74(10) . . ?
N2 C9 C10 106.24(9) . . ?
C12 C9 C10 110.37(11) . . ?
N2 C9 C11 110.15(9) . . ?
C12 C9 C11 110.60(10) . . ?
C10 C9 C11 109.64(11) . . ?
C8 N1 C1 105.46(8) . . ?
C8 N2 C9 126.73(9) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
