# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_2H6M_H2
_database_code_depnum_ccdc_archive 'CCDC 1815097'
_audit_update_record             
;
2018-01-06 deposited with the CCDC.
2018-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.0262(12)
_cell_length_b                   13.512(3)
_cell_length_c                   14.157(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.212(2)
_cell_angle_gamma                90
_cell_volume                     1126.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    2703
_cell_measurement_theta_min      2.944
_cell_measurement_theta_max      28.421

_exptl_crystal_description       prism

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            4282
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.107
_diffrn_reflns_theta_max         29.219
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.598
_diffrn_measured_fraction_theta_full 0.603
_diffrn_reflns_Laue_measured_fraction_max 0.598
_diffrn_reflns_Laue_measured_fraction_full 0.603
_diffrn_reflns_point_group_measured_fraction_max 0.598
_diffrn_reflns_point_group_measured_fraction_full 0.603
_reflns_number_total             1827
_reflns_number_gt                1248
_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       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXT (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1827
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.84828(19) 0.17079(9) 0.25799(8) 0.0189(3) Uani 1 1 d . . . . .
N1 N 0.5188(2) 0.28472(10) 0.29654(9) 0.0156(3) Uani 1 1 d . . . . .
H3 H 0.5418 0.2529 0.2452 0.019 Uiso 1 1 calc R U . . .
C1 C 1.2475(3) 0.10884(15) 0.48346(13) 0.0300(5) Uani 1 1 d . . . . .
H1 H 1.3802 0.0705 0.5060 0.036 Uiso 1 1 calc R U . . .
O2 O 0.8824(2) 0.27081(9) 0.58406(8) 0.0218(3) Uani 1 1 d . . . . .
H1O H 0.7676 0.3034 0.5571 0.033 Uiso 1 1 calc R U . . .
N2 N 0.5700(2) 0.33567(10) 0.44969(9) 0.0167(3) Uani 1 1 d . . . . .
C2 C 1.1555(3) 0.16246(14) 0.54886(13) 0.0253(4) Uani 1 1 d . . . . .
H2 H 1.2250 0.1611 0.6157 0.030 Uiso 1 1 calc R U . . .
C3 C 0.9615(3) 0.21817(12) 0.51654(11) 0.0175(4) Uani 1 1 d . . . . .
C4 C 0.8537(3) 0.21951(11) 0.41798(11) 0.0152(3) Uani 1 1 d . . . . .
C5 C 0.9552(3) 0.16505(12) 0.35341(11) 0.0170(4) Uani 1 1 d . . . . .
C6 C 1.1502(3) 0.10981(13) 0.38591(13) 0.0247(4) Uani 1 1 d . . . . .
H6 H 1.2162 0.0731 0.3416 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6503(3) 0.27915(11) 0.38767(11) 0.0152(3) Uani 1 1 d . . . . .
C7 C 0.9645(3) 0.12882(13) 0.18902(12) 0.0218(4) Uani 1 1 d . . . . .
H7A H 0.8829 0.1456 0.1235 0.033 Uiso 1 1 calc R U . . .
H7B H 0.9709 0.0567 0.1965 0.033 Uiso 1 1 calc R U . . .
H7C H 1.1191 0.1554 0.1999 0.033 Uiso 1 1 calc R U . . .
C9 C 0.3777(3) 0.38085(12) 0.39656(12) 0.0154(3) Uani 1 1 d . . . . .
C10 C 0.2316(3) 0.44985(12) 0.42415(12) 0.0185(4) Uani 1 1 d . . . . .
H10 H 0.2533 0.4720 0.4891 0.022 Uiso 1 1 calc R U . . .
C11 C 0.0549(3) 0.48477(12) 0.35411(12) 0.0205(4) Uani 1 1 d . . . . .
H11 H -0.0464 0.5320 0.3713 0.025 Uiso 1 1 calc R U . . .
C12 C 0.0203(3) 0.45243(12) 0.25767(13) 0.0197(4) Uani 1 1 d . . . . .
H12 H -0.1044 0.4777 0.2114 0.024 Uiso 1 1 calc R U . . .
C13 C 0.1650(3) 0.38427(12) 0.22883(12) 0.0185(4) Uani 1 1 d . . . . .
H13 H 0.1433 0.3625 0.1637 0.022 Uiso 1 1 calc R U . . .
C14 C 0.3431(3) 0.34942(12) 0.29978(12) 0.0153(3) Uani 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 1.370(2) . ?
O1 C7 1.4333(17) . ?
N1 C8 1.366(2) . ?
N1 C14 1.381(2) . ?
N1 H3 0.8800 . ?
C1 C2 1.381(2) . ?
C1 C6 1.381(3) . ?
C1 H1 0.9500 . ?
O2 C3 1.3565(18) . ?
O2 H1O 0.8400 . ?
N2 C8 1.3296(19) . ?
N2 C9 1.383(2) . ?
C2 C3 1.384(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(2) . ?
C4 C5 1.410(2) . ?
C4 C8 1.454(2) . ?
C5 C6 1.386(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C10 1.394(2) . ?
C9 C14 1.407(2) . ?
C10 C11 1.376(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.406(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?

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
C5 O1 C7 116.98(13) . . ?
C8 N1 C14 107.41(13) . . ?
C8 N1 H3 126.3 . . ?
C14 N1 H3 126.3 . . ?
C2 C1 C6 121.33(18) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C3 O2 H1O 109.5 . . ?
C8 N2 C9 105.93(13) . . ?
C1 C2 C3 119.62(17) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
O2 C3 C2 116.78(15) . . ?
O2 C3 C4 122.26(14) . . ?
C2 C3 C4 120.96(15) . . ?
C3 C4 C5 117.58(15) . . ?
C3 C4 C8 118.86(13) . . ?
C5 C4 C8 123.52(14) . . ?
O1 C5 C6 123.12(14) . . ?
O1 C5 C4 115.58(14) . . ?
C6 C5 C4 121.30(15) . . ?
C1 C6 C5 119.17(15) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N2 C8 N1 111.88(14) . . ?
N2 C8 C4 121.69(14) . . ?
N1 C8 C4 126.43(13) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C9 C10 130.48(15) . . ?
N2 C9 C14 109.31(13) . . ?
C10 C9 C14 120.17(16) . . ?
C11 C10 C9 117.77(15) . . ?
C11 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C10 C11 C12 121.75(15) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 121.23(17) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 116.75(15) . . ?
C12 C13 H13 121.6 . . ?
C14 C13 H13 121.6 . . ?
N1 C14 C13 132.18(15) . . ?
N1 C14 C9 105.46(14) . . ?
C13 C14 C9 122.34(14) . . ?

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_2H4M_H
_database_code_depnum_ccdc_archive 'CCDC 1815098'
_audit_update_record             
;
2018-01-06 deposited with the CCDC.
2018-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.2231(10)
_cell_length_b                   6.7181(9)
_cell_length_c                   22.977(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.381(2)
_cell_angle_gamma                90
_cell_volume                     1103.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    3574
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      28.969

_exptl_crystal_description       prism

_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            6350
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0120
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.792
_diffrn_reflns_theta_max         29.141
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2712
_reflns_number_gt                2343
_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       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXT (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2016)'

_computing_molecular_graphics    'XSHELXle (Bruker AXS)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0523P)²+0.3976P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2712
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_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 0.61027(11) 0.62949(12) 0.70103(3) 0.01847(19) Uani 1 1 d . . . . .
N1 N 0.79447(13) 0.15919(14) 0.46938(4) 0.0157(2) Uani 1 1 d . . . . .
H1N H 0.786702 0.056441 0.492661 0.019 Uiso 1 1 calc R U . . .
C1 C 0.64482(14) 0.57160(16) 0.64668(5) 0.0153(2) Uani 1 1 d . . . . .
O2 O 0.72478(12) 0.76518(11) 0.50526(3) 0.01948(19) Uani 1 1 d . . . . .
H1 H 0.744717 0.704987 0.474733 0.029 Uiso 1 1 calc R U . . .
N2 N 0.79084(12) 0.47517(14) 0.43848(4) 0.0153(2) Uani 1 1 d . . . . .
C2 C 0.66464(15) 0.70338(16) 0.60152(5) 0.0154(2) Uani 1 1 d . . . . .
H2 H 0.650702 0.842391 0.607096 0.019 Uiso 1 1 calc R U . . .
C3 C 0.70507(14) 0.63101(16) 0.54797(5) 0.0145(2) Uani 1 1 d . . . . .
C4 C 0.72486(14) 0.42527(16) 0.53892(4) 0.0141(2) Uani 1 1 d . . . . .
C5 C 0.70117(16) 0.29651(16) 0.58518(5) 0.0179(2) Uani 1 1 d . . . . .
H5 H 0.713021 0.157162 0.579730 0.021 Uiso 1 1 calc R U . . .
C6 C 0.66113(16) 0.36609(17) 0.63841(5) 0.0186(2) Uani 1 1 d . . . . .
H6 H 0.644813 0.275829 0.669081 0.022 Uiso 1 1 calc R U . . .
C8 C 0.76963(14) 0.35461(16) 0.48290(5) 0.0143(2) Uani 1 1 d . . . . .
C7 C 0.59197(16) 0.83899(17) 0.71042(5) 0.0187(2) Uani 1 1 d . . . . .
H7A H 0.567285 0.862434 0.750676 0.028 Uiso 1 1 calc R U . . .
H7B H 0.487971 0.891453 0.682460 0.028 Uiso 1 1 calc R U . . .
H7C H 0.708137 0.906377 0.704526 0.028 Uiso 1 1 calc R U . . .
C9 C 0.82970(14) 0.35221(16) 0.39327(5) 0.0149(2) Uani 1 1 d . . . . .
C10 C 0.86054(15) 0.39773(17) 0.33611(5) 0.0176(2) Uani 1 1 d . . . . .
H10 H 0.855699 0.531155 0.322281 0.021 Uiso 1 1 calc R U . . .
C11 C 0.89847(15) 0.24121(17) 0.30031(5) 0.0187(2) Uani 1 1 d . . . . .
H11 H 0.919747 0.268371 0.261247 0.022 Uiso 1 1 calc R U . . .
C12 C 0.90617(15) 0.04405(18) 0.32034(5) 0.0194(2) Uani 1 1 d . . . . .
H12 H 0.934545 -0.058981 0.294731 0.023 Uiso 1 1 calc R U . . .
C13 C 0.87340(15) -0.00466(17) 0.37667(5) 0.0184(2) Uani 1 1 d . . . . .
H13 H 0.877551 -0.138417 0.390210 0.022 Uiso 1 1 calc R U . . .
C14 C 0.83411(14) 0.15303(16) 0.41225(5) 0.0153(2) Uani 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 C1 1.3653(12) . ?
O1 C7 1.4329(14) . ?
N1 C8 1.3669(14) . ?
N1 C14 1.3844(13) . ?
N1 H1N 0.8800 . ?
C1 C2 1.3870(15) . ?
C1 C6 1.4010(16) . ?
O2 C3 1.3551(13) . ?
O2 H1 0.8400 . ?
N2 C8 1.3293(13) . ?
N2 C9 1.3875(13) . ?
C2 C3 1.3930(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.4081(15) . ?
C4 C5 1.4001(15) . ?
C4 C8 1.4518(14) . ?
C5 C6 1.3788(15) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C10 1.3974(14) . ?
C9 C14 1.4063(15) . ?
C10 C11 1.3869(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.4007(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3883(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3924(15) . ?
C13 H13 0.9500 . ?

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
C1 O1 C7 116.78(9) . . ?
C8 N1 C14 107.24(9) . . ?
C8 N1 H1N 126.4 . . ?
C14 N1 H1N 126.4 . . ?
O1 C1 C2 123.71(10) . . ?
O1 C1 C6 115.78(10) . . ?
C2 C1 C6 120.51(10) . . ?
C3 O2 H1 109.5 . . ?
C8 N2 C9 105.71(9) . . ?
C1 C2 C3 119.72(10) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
O2 C3 C2 117.72(10) . . ?
O2 C3 C4 121.49(10) . . ?
C2 C3 C4 120.79(10) . . ?
C5 C4 C3 117.91(10) . . ?
C5 C4 C8 122.59(10) . . ?
C3 C4 C8 119.50(9) . . ?
C6 C5 C4 121.91(10) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 119.15(10) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N2 C8 N1 112.15(9) . . ?
N2 C8 C4 123.16(10) . . ?
N1 C8 C4 124.68(10) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C9 C10 130.59(10) . . ?
N2 C9 C14 109.40(9) . . ?
C10 C9 C14 120.01(10) . . ?
C11 C10 C9 117.64(10) . . ?
C11 C10 H10 121.2 . . ?
C9 C10 H10 121.2 . . ?
C10 C11 C12 121.59(10) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 121.69(10) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 116.43(10) . . ?
C12 C13 H13 121.8 . . ?
C14 C13 H13 121.8 . . ?
N1 C14 C13 131.88(10) . . ?
N1 C14 C9 105.50(9) . . ?
C13 C14 C9 122.63(10) . . ?

_refine_diff_density_max         0.346
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_2H3M_H
_database_code_depnum_ccdc_archive 'CCDC 1815099'
_audit_update_record             
;
2018-01-06 deposited with the CCDC.
2018-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7700(13)
_cell_length_b                   11.889(2)
_cell_length_c                   12.200(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.181(2)
_cell_angle_gamma                90
_cell_volume                     1124.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    2943
_cell_measurement_theta_min      2.395
_cell_measurement_theta_max      28.787

_exptl_crystal_description       prism

_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            6651
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.395
_diffrn_reflns_theta_max         29.037
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2768
_reflns_number_gt                2279
_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       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXT (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2016)'

_computing_molecular_graphics    'XSHELXle (Bruker AXS)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0552P)²+0.2997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2768
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 1.06859(11) 0.84030(8) 0.48888(7) 0.0196(2) Uani 1 1 d . . . . .
N1 N 0.42253(12) 0.70321(8) 0.21201(8) 0.0145(2) Uani 1 1 d . . . . .
H1N H 0.427427 0.733189 0.146364 0.017 Uiso 1 1 calc R U . . .
C1 C 1.03029(15) 0.87772(10) 0.29126(10) 0.0160(2) Uani 1 1 d . . . . .
H1 H 1.137412 0.916160 0.290692 0.019 Uiso 1 1 calc R U . . .
O2 O 0.77810(11) 0.73448(8) 0.48812(7) 0.0178(2) Uani 1 1 d . . . . .
H2 H 0.684195 0.699425 0.479725 0.027 Uiso 1 1 calc R U . . .
N2 N 0.50102(12) 0.65617(8) 0.38618(8) 0.0146(2) Uani 1 1 d . . . . .
C2 C 0.97816(14) 0.83356(10) 0.38819(9) 0.0147(2) Uani 1 1 d . . . . .
C3 C 0.81944(14) 0.77639(10) 0.38975(9) 0.0140(2) Uani 1 1 d . . . . .
C4 C 0.71276(14) 0.76648(9) 0.29252(9) 0.0132(2) Uani 1 1 d . . . . .
C5 C 0.76816(14) 0.81125(10) 0.19414(9) 0.0146(2) Uani 1 1 d . . . . .
H5 H 0.697327 0.803930 0.127700 0.018 Uiso 1 1 calc R U . . .
C6 C 0.92509(15) 0.86575(10) 0.19396(9) 0.0158(2) Uani 1 1 d . . . . .
H6 H 0.961884 0.895335 0.127212 0.019 Uiso 1 1 calc R U . . .
C7 C 1.22261(17) 0.90594(12) 0.49412(11) 0.0242(3) Uani 1 1 d . . . . .
H7A H 1.273852 0.907334 0.569921 0.036 Uiso 1 1 calc R U . . .
H7B H 1.195097 0.982880 0.469910 0.036 Uiso 1 1 calc R U . . .
H7C H 1.304719 0.872721 0.446119 0.036 Uiso 1 1 calc R U . . .
C9 C 0.33845(14) 0.61188(9) 0.35771(9) 0.0136(2) Uani 1 1 d . . . . .
C8 C 0.54702(14) 0.70902(9) 0.29670(9) 0.0136(2) Uani 1 1 d . . . . .
C10 C 0.23297(15) 0.54367(10) 0.41765(10) 0.0167(2) Uani 1 1 d . . . . .
H10 H 0.266218 0.522380 0.491217 0.020 Uiso 1 1 calc R U . . .
C11 C 0.07807(15) 0.50834(10) 0.36561(10) 0.0184(3) Uani 1 1 d . . . . .
H11 H 0.004608 0.461010 0.404146 0.022 Uiso 1 1 calc R U . . .
C12 C 0.02656(15) 0.54056(10) 0.25738(10) 0.0178(3) Uani 1 1 d . . . . .
H12 H -0.081672 0.515617 0.225023 0.021 Uiso 1 1 calc R U . . .
C13 C 0.12983(15) 0.60780(10) 0.19676(10) 0.0157(2) Uani 1 1 d . . . . .
H13 H 0.095121 0.629841 0.123628 0.019 Uiso 1 1 calc R U . . .
C14 C 0.28756(14) 0.64159(9) 0.24852(9) 0.0136(2) Uani 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 C2 1.3724(13) . ?
O1 C7 1.4263(15) . ?
N1 C8 1.3646(14) . ?
N1 C14 1.3795(15) . ?
N1 H1N 0.8800 . ?
C1 C2 1.3813(16) . ?
C1 C6 1.3987(16) . ?
C1 H1 0.9500 . ?
O2 C3 1.3594(14) . ?
O2 H2 0.8400 . ?
N2 C8 1.3308(15) . ?
N2 C9 1.3890(15) . ?
C2 C3 1.4095(16) . ?
C3 C4 1.4017(15) . ?
C4 C5 1.4088(16) . ?
C4 C8 1.4620(16) . ?
C5 C6 1.3809(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C10 1.3970(16) . ?
C9 C14 1.4067(16) . ?
C10 C11 1.3845(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.4049(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3843(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3962(16) . ?
C13 H13 0.9500 . ?

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 O1 C7 116.44(9) . . ?
C8 N1 C14 107.21(9) . . ?
C8 N1 H1N 126.4 . . ?
C14 N1 H1N 126.4 . . ?
C2 C1 C6 119.88(11) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 O2 H2 109.5 . . ?
C8 N2 C9 105.52(9) . . ?
O1 C2 C1 125.54(10) . . ?
O1 C2 C3 114.04(10) . . ?
C1 C2 C3 120.42(10) . . ?
O2 C3 C4 123.58(10) . . ?
O2 C3 C2 116.87(10) . . ?
C4 C3 C2 119.54(10) . . ?
C3 C4 C5 119.39(10) . . ?
C3 C4 C8 118.54(10) . . ?
C5 C4 C8 122.07(10) . . ?
C6 C5 C4 120.22(10) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.52(11) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C9 C10 130.29(11) . . ?
N2 C9 C14 109.23(10) . . ?
C10 C9 C14 120.42(10) . . ?
N2 C8 N1 112.29(10) . . ?
N2 C8 C4 122.63(10) . . ?
N1 C8 C4 125.09(10) . . ?
C11 C10 C9 117.36(11) . . ?
C11 C10 H10 121.3 . . ?
C9 C10 H10 121.3 . . ?
C10 C11 C12 121.79(11) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 121.54(11) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 116.65(11) . . ?
C12 C13 H13 121.7 . . ?
C14 C13 H13 121.7 . . ?
N1 C14 C13 132.04(11) . . ?
N1 C14 C9 105.74(10) . . ?
C13 C14 C9 122.20(11) . . ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.045

