# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_OME2PYX
_database_code_depnum_ccdc_archive 'CCDC 2070982'
loop_
_audit_author_name
_audit_author_address
'SUMIT KAMBLE'
;CSIR CSMCRI Bhavnagar Gujarat
India
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_OME2PYX             
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        45% Check
RESPONSE: NA
;
_vrf_PLAT351_OME2PYX             
;
PROBLEM: Long   C-H (X0.96,N1.08A)  C8       - H8       .       1.12 Ang.
RESPONSE: NA
;
_vrf_PLAT905_OME2PYX             
;
PROBLEM: Negative K value in the Analysis of Variance ...    -28.864 Report
RESPONSE: NA
;
# Added during the CSD deposition process: Wednesday 17 March 2021 07:57 AM
# end Validation Reply Form

_chemical_name_systematic        ?
_chemical_name_common            ORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         282.33

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.8817(7)
_cell_length_b                   7.5056(4)
_cell_length_c                   16.1720(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.587(2)
_cell_angle_gamma                90
_cell_volume                     1453.92(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4013
_cell_measurement_theta_min      2.6154
_cell_measurement_theta_max      27.7450
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       BLOCKS
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.515
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.083
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600

_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.9570
_exptl_absorpt_correction_T_max  0.9930

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'MICRO FOCUS TUBE'
_diffrn_source_type              ?

_diffrn_radiation_type           Mok\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            28691
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         33.20
_diffrn_reflns_theta_full        33.20
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
;

_reflns_number_total             5542
_reflns_number_gt                2493
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_gt          0.1717
_refine_ls_wR_factor_ref         0.2294
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_number_reflns         5542
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0845P)²+0.3642P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.00813(13) -0.0474(2) 0.39925(11) 0.0712(5) Uani d . . . 1 . .
O O2 0.43059(13) 0.3418(2) 0.13311(10) 0.0627(4) Uani d . . . 1 . .
N N1 0.07613(15) 0.2080(2) 0.47292(13) 0.0599(5) Uani d . . . 1 . .
N N2 0.1486(2) -0.1578(3) 0.26911(17) 0.0945(8) Uani d . . . 1 . .
C C1 0.38851(18) 0.2043(3) 0.33709(15) 0.0545(5) Uani d . . . 1 . .
C C2 0.44036(18) 0.2232(3) 0.27626(15) 0.0551(5) Uani d . . . 1 . .
C C3 0.38892(17) 0.3193(2) 0.19941(14) 0.0491(4) Uani d . . . 1 . .
C C4 0.28816(18) 0.4023(3) 0.18575(14) 0.0540(5) Uani d . . . 1 . .
C C5 0.23762(18) 0.3823(3) 0.24683(14) 0.0535(5) Uani d . . . 1 . .
C C6 0.28536(16) 0.2798(2) 0.32275(13) 0.0468(4) Uani d . . . 1 . .
C C7 0.22673(17) 0.2458(3) 0.38655(14) 0.0497(5) Uani d . . . 1 . .
C C8 0.19337(18) 0.4131(3) 0.42459(14) 0.0531(5) Uani d . . . 1 . .
C C9 0.2894(2) 0.5415(3) 0.46630(17) 0.0664(6) Uani d . . . 1 . .
H H9A 0.352662 0.476721 0.50717 0.08 Uiso calc U . R 1 . .
H H9B 0.311713 0.59155 0.420059 0.08 Uiso calc U . R 1 . .
C C10 0.2592(2) 0.6908(3) 0.51563(18) 0.0723(7) Uani d . . . 1 . .
H H10A 0.322928 0.769302 0.540691 0.087 Uiso calc U . R 1 . .
H H10B 0.19857 0.759593 0.474187 0.087 Uiso calc U . R 1 . .
C C11 0.2247(2) 0.6228(3) 0.58861(17) 0.0730(7) Uani d . . . 1 . .
H H11A 0.290943 0.596521 0.64026 0.088 Uiso calc U . R 1 . .
H H11B 0.183473 0.715419 0.605194 0.088 Uiso calc U . R 1 . .
C C12 0.1540(2) 0.4594(3) 0.56293(16) 0.0628(6) Uani d . . . 1 . .
C C13 0.14174(17) 0.3649(3) 0.49071(14) 0.0514(5) Uani d . . . 1 . .
C C14 0.06260(17) 0.0911(3) 0.40806(15) 0.0558(5) Uani d . . . 1 . .
C C15 0.11925(18) 0.1352(3) 0.34247(14) 0.0541(5) Uani d . . . 1 . .
H H15 0.067154 0.208802 0.295323 0.065 Uiso calc U . R 1 . .
C C16 0.13648(19) -0.0294(3) 0.30117(15) 0.0609(6) Uani d . . . 1 . .
C C17 0.5313(2) 0.2517(3) 0.14257(19) 0.0766(7) Uani d . . . 1 . .
H H17A 0.547961 0.268971 0.089937 0.115 Uiso calc U . R 1 . .
H H17B 0.522858 0.126731 0.151086 0.115 Uiso calc U . R 1 . .
H H17C 0.591174 0.298484 0.193071 0.115 Uiso calc U . R 1 . .
H H1 0.4264(18) 0.132(3) 0.3924(15) 0.060(6) Uiso d . . . 1 . .
H H2 0.515(2) 0.167(3) 0.2874(16) 0.076(7) Uiso d . . . 1 . .
H H1A 0.041(2) 0.175(4) 0.5120(19) 0.089(9) Uiso d . . . 1 . .
H H4 0.2548(18) 0.474(3) 0.1339(15) 0.070(7) Uiso d . . . 1 . .
H H5 0.1658(19) 0.438(3) 0.2349(15) 0.066(6) Uiso d . . . 1 . .
H H7 0.2815(19) 0.169(3) 0.4413(15) 0.064(6) Uiso d . . . 1 . .
H H8 0.131(2) 0.481(4) 0.3652(17) 0.086(8) Uiso d . . . 1 . .
H H12 0.1173(19) 0.419(3) 0.6027(16) 0.070(7) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C14 . 1.233(2) ?
O2 C3 . 1.375(2) ?
O2 C17 . 1.421(3) ?
N1 C14 . 1.329(3) ?
N1 C13 . 1.416(3) ?
N1 H1A . 0.93(3) ?
N2 C16 . 1.132(3) ?
C1 C6 . 1.383(3) ?
C1 C2 . 1.385(3) ?
C1 H1 . 1.01(2) ?
C2 C3 . 1.378(3) ?
C2 H2 . 1.00(3) ?
C3 C4 . 1.382(3) ?
C4 C5 . 1.377(3) ?
C4 H4 . 0.96(2) ?
C5 C6 . 1.386(3) ?
C5 H5 . 0.97(2) ?
C6 C7 . 1.508(2) ?
C7 C8 . 1.528(3) ?
C7 C15 . 1.545(3) ?
C7 H7 . 1.08(2) ?
C8 C13 . 1.497(3) ?
C8 C9 . 1.517(3) ?
C8 H8 . 1.12(3) ?
C9 C10 . 1.507(3) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 C11 . 1.496(3) ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C11 C12 . 1.493(3) ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C12 C13 . 1.325(3) ?
C12 H12 . 0.98(2) ?
C14 C15 . 1.529(3) ?
C15 C16 . 1.460(3) ?
C15 H15 . 0.98 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O2 C17 . . 117.43(18) ?
C14 N1 C13 . . 127.20(17) ?
C14 N1 H1A . . 113.7(17) ?
C13 N1 H1A . . 118.9(17) ?
C6 C1 C2 . . 121.6(2) ?
C6 C1 H1 . . 119.5(12) ?
C2 C1 H1 . . 118.9(12) ?
C3 C2 C1 . . 119.78(19) ?
C3 C2 H2 . . 119.6(14) ?
C1 C2 H2 . . 120.6(14) ?
O2 C3 C2 . . 124.88(18) ?
O2 C3 C4 . . 115.65(18) ?
C2 C3 C4 . . 119.47(18) ?
C5 C4 C3 . . 120.02(19) ?
C5 C4 H4 . . 120.8(13) ?
C3 C4 H4 . . 119.1(13) ?
C4 C5 C6 . . 121.54(19) ?
C4 C5 H5 . . 118.6(14) ?
C6 C5 H5 . . 119.8(14) ?
C1 C6 C5 . . 117.50(17) ?
C1 C6 C7 . . 120.52(18) ?
C5 C6 C7 . . 121.96(18) ?
C6 C7 C8 . . 114.99(16) ?
C6 C7 C15 . . 111.39(16) ?
C8 C7 C15 . . 106.87(16) ?
C6 C7 H7 . . 108.2(12) ?
C8 C7 H7 . . 107.9(12) ?
C15 C7 H7 . . 107.2(12) ?
C13 C8 C9 . . 109.88(17) ?
C13 C8 C7 . . 110.72(16) ?
C9 C8 C7 . . 113.40(17) ?
C13 C8 H8 . . 110.8(13) ?
C9 C8 H8 . . 107.7(14) ?
C7 C8 H8 . . 104.2(13) ?
C10 C9 C8 . . 112.37(19) ?
C10 C9 H9A . . 109.1 ?
C8 C9 H9A . . 109.1 ?
C10 C9 H9B . . 109.1 ?
C8 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.9 ?
C11 C10 C9 . . 112.0(2) ?
C11 C10 H10A . . 109.2 ?
C9 C10 H10A . . 109.2 ?
C11 C10 H10B . . 109.2 ?
C9 C10 H10B . . 109.2 ?
H10A C10 H10B . . 107.9 ?
C12 C11 C10 . . 112.9(2) ?
C12 C11 H11A . . 109.0 ?
C10 C11 H11A . . 109.0 ?
C12 C11 H11B . . 109.0 ?
C10 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
C13 C12 C11 . . 123.2(2) ?
C13 C12 H12 . . 119.0(14) ?
C11 C12 H12 . . 117.8(14) ?
C12 C13 N1 . . 119.51(18) ?
C12 C13 C8 . . 124.08(19) ?
N1 C13 C8 . . 116.41(17) ?
O1 C14 N1 . . 123.49(19) ?
O1 C14 C15 . . 119.94(19) ?
N1 C14 C15 . . 116.57(17) ?
C16 C15 C14 . . 109.04(17) ?
C16 C15 C7 . . 113.86(17) ?
C14 C15 C7 . . 111.82(16) ?
C16 C15 H15 . . 107.3 ?
C14 C15 H15 . . 107.3 ?
C7 C15 H15 . . 107.3 ?
N2 C16 C15 . . 179.2(2) ?
O2 C17 H17A . . 109.5 ?
O2 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O2 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?

