# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1841255'
loop_
_audit_author_name
_audit_author_address
ZMH
;aa
China
;
_audit_update_record             
;
2018-05-03 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;
_audit_creation_date             2018-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.35
_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                   11.350(3)
_cell_length_b                   13.447(4)
_cell_length_c                   10.912(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.139(4)
_cell_angle_gamma                90
_cell_volume                     1582.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5065
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4767
_cell_measurement_theta_min      1.5144
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.408
_exptl_crystal_size_min          0.264
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10516
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         1.888
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3414
_reflns_number_total             3590
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3590
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.104
_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)+(0.0325P)²+0.6398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1050
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C14(H14), C15(H15), C17(H17),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.28155(11) 0.30427(7) 0.36738(11) 0.0393(3) Uani 1 1 d . . . . .
C1 C 0.47567(12) 0.55307(10) 0.29079(13) 0.0248(3) Uani 1 1 d . . . . .
N1 N 0.33909(10) 0.46762(8) 0.36308(11) 0.0247(2) Uani 1 1 d . . . . .
O2 O 0.10973(9) 0.35354(8) 0.47628(10) 0.0332(2) Uani 1 1 d . . . . .
N2 N 0.20083(10) 0.42302(8) 0.46997(11) 0.0283(3) Uani 1 1 d . . . . .
C2 C 0.55861(13) 0.56813(11) 0.22101(14) 0.0305(3) Uani 1 1 d . . . . .
H2 H 0.594698 0.631621 0.219109 0.037 Uiso 1 1 calc R . . . .
C3 C 0.58687(14) 0.48925(11) 0.15524(15) 0.0351(3) Uani 1 1 d . . . . .
H3 H 0.643115 0.498450 0.107420 0.042 Uiso 1 1 calc R . . . .
O3 O 0.09704(10) 0.99612(7) 0.36700(10) 0.0370(3) Uani 1 1 d . . . . .
C4 C 0.53438(15) 0.39614(11) 0.15763(16) 0.0381(4) Uani 1 1 d . . . . .
H4 H 0.555916 0.342981 0.111361 0.046 Uiso 1 1 calc R . . . .
C5 C 0.45173(14) 0.37860(11) 0.22536(14) 0.0331(3) Uani 1 1 d . . . . .
H5 H 0.416395 0.314713 0.226620 0.040 Uiso 1 1 calc R . . . .
C6 C 0.42258(12) 0.45856(9) 0.29159(13) 0.0245(3) Uani 1 1 d . . . . .
C7 C 0.27217(12) 0.39023(10) 0.39629(13) 0.0272(3) Uani 1 1 d . . . . .
C8 C 0.15280(12) 0.52475(10) 0.45877(14) 0.0302(3) Uani 1 1 d . . . . .
H8A H 0.107402 0.535615 0.521775 0.036 Uiso 1 1 calc R . . . .
H8B H 0.094661 0.535874 0.371088 0.036 Uiso 1 1 calc R . . . .
C9 C 0.26163(12) 0.59732(10) 0.48496(13) 0.0251(3) Uani 1 1 d . . . . .
H9 H 0.311265 0.592301 0.578196 0.030 Uiso 1 1 calc R . . . .
C10 C 0.34247(11) 0.56666(9) 0.40623(12) 0.0239(3) Uani 1 1 d . . . . .
C11 C 0.42447(12) 0.61829(10) 0.36464(13) 0.0277(3) Uani 1 1 d . . . . .
H11 H 0.444841 0.686512 0.381527 0.033 Uiso 1 1 calc R . . . .
C12 C 0.14409(15) 0.31064(12) 0.60220(15) 0.0378(3) Uani 1 1 d . . . . .
H12A H 0.078868 0.264996 0.608376 0.057 Uiso 1 1 calc GR . . . .
H12B H 0.154936 0.363461 0.666650 0.057 Uiso 1 1 calc GR . . . .
H12C H 0.222060 0.274016 0.617979 0.057 Uiso 1 1 calc GR . . . .
C13 C 0.21821(11) 0.70410(10) 0.45695(13) 0.0243(3) Uani 1 1 d . . . . .
C14 C 0.24710(12) 0.77567(10) 0.55278(13) 0.0286(3) Uani 1 1 d . . . . .
H14 H 0.294551 0.757200 0.637874 0.034 Uiso 1 1 calc R . . . .
C15 C 0.20847(13) 0.87432(10) 0.52799(14) 0.0302(3) Uani 1 1 d . . . . .
H15 H 0.229360 0.922132 0.595429 0.036 Uiso 1 1 calc R . . . .
C16 C 0.13946(12) 0.90170(10) 0.40416(13) 0.0273(3) Uani 1 1 d . . . . .
C17 C 0.10964(12) 0.83078(11) 0.30632(13) 0.0292(3) Uani 1 1 d . . . . .
H17 H 0.062341 0.849284 0.221186 0.035 Uiso 1 1 calc R . . . .
C18 C 0.14857(12) 0.73379(10) 0.33268(13) 0.0278(3) Uani 1 1 d . . . . .
H18 H 0.127665 0.686135 0.265046 0.033 Uiso 1 1 calc R . . . .
C19 C 0.13248(16) 1.07356(11) 0.46123(17) 0.0414(4) Uani 1 1 d . . . . .
H19A H 0.099509 1.137195 0.421328 0.062 Uiso 1 1 calc GR . . . .
H19B H 0.223115 1.077238 0.494851 0.062 Uiso 1 1 calc GR . . . .
H19C H 0.099079 1.059298 0.532069 0.062 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 C7 1.2116(17) . ?
C1 C2 1.3975(19) . ?
C1 C6 1.4077(18) . ?
C1 C11 1.4311(19) . ?
N1 C6 1.4076(17) . ?
N1 C7 1.4009(17) . ?
N1 C10 1.4091(16) . ?
O2 N2 1.4111(14) . ?
O2 C12 1.4279(18) . ?
N2 C7 1.3792(18) . ?
N2 C8 1.4635(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.373(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
O3 C16 1.3735(17) . ?
O3 C19 1.4303(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3916(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5296(18) . ?
C9 H9 1.0000 . ?
C9 C10 1.4969(18) . ?
C9 C13 1.5180(18) . ?
C10 C11 1.3480(19) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.3833(19) . ?
C13 C18 1.3984(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3969(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(2) . ?
C16 C17 1.392(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.3784(19) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C2 C1 C6 119.77(12) . . ?
C2 C1 C11 132.73(13) . . ?
C6 C1 C11 107.46(11) . . ?
C6 N1 C10 108.30(10) . . ?
C7 N1 C6 126.28(11) . . ?
C7 N1 C10 125.18(11) . . ?
N2 O2 C12 109.25(10) . . ?
O2 N2 C8 111.31(10) . . ?
C7 N2 O2 112.89(11) . . ?
C7 N2 C8 121.41(11) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.64(13) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.97(14) . . ?
C4 C3 H3 119.5 . . ?
C16 O3 C19 117.81(12) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 121.97(14) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 121.4 . . ?
C4 C5 C6 117.14(13) . . ?
C6 C5 H5 121.4 . . ?
N1 C6 C1 106.78(11) . . ?
C5 C6 C1 121.52(13) . . ?
C5 C6 N1 131.65(12) . . ?
O1 C7 N1 122.87(13) . . ?
O1 C7 N2 124.89(13) . . ?
N2 C7 N1 112.17(11) . . ?
N2 C8 H8A 109.9 . . ?
N2 C8 H8B 109.9 . . ?
N2 C8 C9 108.82(11) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
C8 C9 H9 108.3 . . ?
C10 C9 C8 108.70(11) . . ?
C10 C9 H9 108.3 . . ?
C10 C9 C13 111.32(11) . . ?
C13 C9 C8 111.91(11) . . ?
C13 C9 H9 108.3 . . ?
N1 C10 C9 119.63(11) . . ?
C11 C10 N1 108.91(11) . . ?
C11 C10 C9 131.46(12) . . ?
C1 C11 H11 125.7 . . ?
C10 C11 C1 108.54(12) . . ?
C10 C11 H11 125.7 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C9 121.34(12) . . ?
C14 C13 C18 117.63(12) . . ?
C18 C13 C9 121.02(12) . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.87(13) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.33(13) . . ?
C16 C15 H15 120.3 . . ?
O3 C16 C15 125.02(13) . . ?
O3 C16 C17 115.32(12) . . ?
C15 C16 C17 119.66(13) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.16(13) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.3 . . ?
C17 C18 C13 121.34(13) . . ?
C17 C18 H18 119.3 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.0(2) . . . . ?
N1 C10 C11 C1 0.81(15) . . . . ?
O2 N2 C7 O1 -18.57(19) . . . . ?
O2 N2 C7 N1 164.53(10) . . . . ?
O2 N2 C8 C9 166.48(10) . . . . ?
N2 C8 C9 C10 48.69(14) . . . . ?
N2 C8 C9 C13 172.04(11) . . . . ?
C2 C1 C6 N1 -176.87(11) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C2 C1 C11 C10 176.35(14) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
O3 C16 C17 C18 179.39(12) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C4 C5 C6 N1 176.38(14) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
C6 C1 C11 C10 -1.14(15) . . . . ?
C6 N1 C7 O1 1.3(2) . . . . ?
C6 N1 C7 N2 178.28(11) . . . . ?
C6 N1 C10 C9 179.81(11) . . . . ?
C6 N1 C10 C11 -0.18(14) . . . . ?
C7 N1 C6 C1 -175.17(12) . . . . ?
C7 N1 C6 C5 7.5(2) . . . . ?
C7 N1 C10 C9 -5.48(19) . . . . ?
C7 N1 C10 C11 174.53(12) . . . . ?
C7 N2 C8 C9 -56.85(16) . . . . ?
C8 N2 C7 O1 -154.63(14) . . . . ?
C8 N2 C7 N1 28.47(17) . . . . ?
C8 C9 C10 N1 -22.58(16) . . . . ?
C8 C9 C10 C11 157.41(14) . . . . ?
C8 C9 C13 C14 118.53(14) . . . . ?
C8 C9 C13 C18 -62.17(16) . . . . ?
C9 C10 C11 C1 -179.17(13) . . . . ?
C9 C13 C14 C15 179.51(12) . . . . ?
C9 C13 C18 C17 -179.50(12) . . . . ?
C10 N1 C6 C1 -0.53(14) . . . . ?
C10 N1 C6 C5 -177.82(14) . . . . ?
C10 N1 C7 O1 -172.47(13) . . . . ?
C10 N1 C7 N2 4.51(18) . . . . ?
C10 C9 C13 C14 -119.60(13) . . . . ?
C10 C9 C13 C18 59.70(16) . . . . ?
C11 C1 C2 C3 -177.69(15) . . . . ?
C11 C1 C6 N1 1.00(14) . . . . ?
C11 C1 C6 C5 178.63(13) . . . . ?
C12 O2 N2 C7 108.05(13) . . . . ?
C12 O2 N2 C8 -111.42(13) . . . . ?
C13 C9 C10 N1 -146.29(12) . . . . ?
C13 C9 C10 C11 33.70(19) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C13 C18 C17 -0.17(19) . . . . ?
C14 C15 C16 O3 -179.31(13) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C16 C17 C18 C13 0.1(2) . . . . ?
C18 C13 C14 C15 0.2(2) . . . . ?
C19 O3 C16 C15 3.8(2) . . . . ?
C19 O3 C16 C17 -175.54(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
