# 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_192225_mzt_21b_0m_tw
_database_code_depnum_ccdc_archive 'CCDC 1977761'
loop_
_audit_author_name
_audit_author_address
ZT.Mao
; Zhejiang University of Technology
China
;
_audit_update_record             
;
2020-01-15 deposited with the CCDC.	2020-08-12 downloaded from the CCDC.
;
_audit_creation_date             2019-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N3 O2'
_chemical_formula_sum            'C16 H15 N3 O2'
_chemical_formula_weight         281.31
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   19.365(9)
_cell_length_b                   10.189(4)
_cell_length_c                   6.932(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.906(17)
_cell_angle_gamma                90
_cell_volume                     1357.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5493
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0813 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.8998.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2970
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.135
_diffrn_reflns_theta_min         2.262
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2566
_reflns_number_total             2970
_reflns_special_details          
;
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.187
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2970
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0657P)²+0.5186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1361
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.668(3)
 0.332(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.22518(6) 0.86922(11) 0.76946(19) 0.0234(3) Uani 1 1 d . . . . .
O2 O 0.15539(7) 1.04613(13) 0.7565(3) 0.0444(4) Uani 1 1 d . . . . .
N1 N 0.10061(7) 0.45522(14) 0.7504(3) 0.0280(4) Uani 1 1 d . . . . .
N2 N 0.22342(7) 0.41865(14) 0.7606(3) 0.0279(4) Uani 1 1 d . . . . .
N3 N 0.06777(7) 0.67958(14) 0.7468(2) 0.0247(3) Uani 1 1 d . . . . .
C1 C 0.15723(9) 0.38011(17) 0.7588(3) 0.0321(5) Uani 1 1 d . . . . .
H1 H 0.149733 0.288108 0.764166 0.038 Uiso 1 1 calc R . . . .
C2 C 0.23779(8) 0.54820(16) 0.7558(3) 0.0209(3) Uani 1 1 d . . . . .
C3 C 0.18334(8) 0.63968(16) 0.7545(3) 0.0205(4) Uani 1 1 d . . . . .
C4 C 0.11584(8) 0.58314(16) 0.7496(3) 0.0226(4) Uani 1 1 d . . . . .
C5 C 0.10123(9) 0.79959(16) 0.7527(3) 0.0243(4) Uani 1 1 d . . . . .
H5 H 0.079192 0.882880 0.753026 0.029 Uiso 1 1 calc R . . . .
C6 C 0.17111(8) 0.77897(15) 0.7580(3) 0.0208(4) Uani 1 1 d . . . . .
C7 C 0.31260(8) 0.57757(16) 0.7466(3) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.33512(8) 0.68822(16) 0.6538(2) 0.0218(4) Uani 1 1 d . . . . .
H8 H 0.302221 0.752470 0.603569 0.026 Uiso 1 1 calc R . . . .
C9 C 0.40495(9) 0.70577(17) 0.6339(2) 0.0226(4) Uani 1 1 d . . . . .
H9 H 0.419146 0.781999 0.570308 0.027 Uiso 1 1 calc R . . . .
C10 C 0.45465(8) 0.61345(17) 0.7058(3) 0.0228(4) Uani 1 1 d . . . . .
C11 C 0.43194(9) 0.50290(17) 0.7989(3) 0.0243(4) Uani 1 1 d . . . . .
H11 H 0.464957 0.439069 0.849917 0.029 Uiso 1 1 calc R . . . .
C12 C 0.36239(9) 0.48431(16) 0.8184(3) 0.0230(4) Uani 1 1 d . . . . .
H12 H 0.348218 0.407652 0.881048 0.028 Uiso 1 1 calc R . . . .
C13 C 0.53054(9) 0.63030(19) 0.6823(3) 0.0305(4) Uani 1 1 d . . . . .
H13A H 0.551993 0.691267 0.781205 0.046 Uiso 1 1 calc GR . . . .
H13B H 0.534907 0.665476 0.552712 0.046 Uiso 1 1 calc GR . . . .
H13C H 0.554034 0.545092 0.697611 0.046 Uiso 1 1 calc GR . . . .
C14 C -0.00676(9) 0.65995(18) 0.7459(3) 0.0325(5) Uani 1 1 d . . . . .
H14A H -0.015439 0.612438 0.863574 0.049 Uiso 1 1 calc GR . . . .
H14B H -0.024832 0.608847 0.631082 0.049 Uiso 1 1 calc GR . . . .
H14C H -0.030163 0.745339 0.742561 0.049 Uiso 1 1 calc GR . . . .
C15 C 0.21249(9) 1.00094(17) 0.7673(3) 0.0247(4) Uani 1 1 d . . . . .
C16 C 0.27897(9) 1.07663(17) 0.7834(3) 0.0288(4) Uani 1 1 d . . . . .
H16A H 0.294272 1.095864 0.920408 0.043 Uiso 1 1 calc GR . . . .
H16B H 0.271612 1.159064 0.710998 0.043 Uiso 1 1 calc GR . . . .
H16C H 0.314649 1.024644 0.729393 0.043 Uiso 1 1 calc GR . . . .


_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 C6 1.3887(19) . ?
O1 C15 1.364(2) . ?
O2 C15 1.192(2) . ?
N1 C1 1.333(2) . ?
N1 C4 1.336(2) . ?
N2 C1 1.339(2) . ?
N2 C2 1.350(2) . ?
N3 C4 1.352(2) . ?
N3 C5 1.382(2) . ?
N3 C14 1.456(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.407(2) . ?
C2 C7 1.488(2) . ?
C3 C4 1.425(2) . ?
C3 C6 1.440(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.366(2) . ?
C7 C8 1.394(2) . ?
C7 C12 1.402(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(2) . ?
C10 C11 1.395(3) . ?
C10 C13 1.508(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.493(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C15 O1 C6 121.15(13) . . ?
C1 N1 C4 112.30(15) . . ?
C1 N2 C2 119.09(14) . . ?
C4 N3 C5 108.84(13) . . ?
C4 N3 C14 125.48(14) . . ?
C5 N3 C14 125.63(14) . . ?
N1 C1 N2 127.85(16) . . ?
N1 C1 H1 116.1 . . ?
N2 C1 H1 116.1 . . ?
N2 C2 C3 119.44(15) . . ?
N2 C2 C7 113.71(14) . . ?
C3 C2 C7 126.83(15) . . ?
C2 C3 C4 114.65(15) . . ?
C2 C3 C6 141.08(15) . . ?
C4 C3 C6 104.27(14) . . ?
N1 C4 N3 123.84(15) . . ?
N1 C4 C3 126.61(15) . . ?
N3 C4 C3 109.54(14) . . ?
N3 C5 H5 125.5 . . ?
C6 C5 N3 108.92(14) . . ?
C6 C5 H5 125.5 . . ?
O1 C6 C3 121.96(14) . . ?
C5 C6 O1 129.62(15) . . ?
C5 C6 C3 108.41(14) . . ?
C8 C7 C2 122.87(15) . . ?
C8 C7 C12 118.18(15) . . ?
C12 C7 C2 118.68(15) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.87(15) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.12(16) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C11 117.87(15) . . ?
C9 C10 C13 121.64(16) . . ?
C11 C10 C13 120.48(16) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.38(16) . . ?
C12 C11 H11 119.3 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.58(16) . . ?
C11 C12 H12 119.7 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 C16 110.77(14) . . ?
O2 C15 O1 123.05(16) . . ?
O2 C15 C16 126.17(16) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.668(3)
2 0.332(3)

