# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_sa-65
_database_code_depnum_ccdc_archive 'CCDC 1949919'
loop_
_audit_author_name
_audit_author_address
'Li Jianxiao'
;South China University of Technology
China
;
_audit_update_record             
;
2019-08-28 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_audit_creation_date             2019-08-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 N2 O2'
_chemical_formula_sum            'C21 H22 N2 O2'
_chemical_formula_weight         334.40
_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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   20.3378(10)
_cell_length_b                   20.3378(10)
_cell_length_c                   18.3367(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7584.5(9)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    2720
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.4430
_cell_measurement_theta_min      2.6310
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2848
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9393
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.003
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00   2.00   1.00    8.00    --  -11.59 -57.00 -90.00   85
  2  ω     50.00  75.00   1.00    8.00    --   11.74-137.00 171.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0136894000
_diffrn_orient_matrix_UB_12      -0.0320765000
_diffrn_orient_matrix_UB_13      0.0018987000
_diffrn_orient_matrix_UB_21      -0.0315774500
_diffrn_orient_matrix_UB_22      -0.0137437500
_diffrn_orient_matrix_UB_23      -0.0060452500
_diffrn_orient_matrix_UB_31      0.0057299000
_diffrn_orient_matrix_UB_32      0.0006009000
_diffrn_orient_matrix_UB_33      -0.0381090000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2539
_reflns_number_total             3350
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.316
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+13.1015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1522
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C10, C11, C12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C10 \\sim C11 \\sim C12: within 2A with sigma of 0.002 and sigma for terminal
atoms of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C2(H2A), C5(H5), C3(H3), C4(H4), C17(H17), C21(H21), C18(H18),
  C20(H20), C19(H19)
4.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.88022(8) 0.33506(8) 0.33409(9) 0.0285(4) Uani 1 1 d . . . . .
O2 O 0.78821(9) 0.45892(8) 0.50046(8) 0.0327(5) Uani 1 1 d . . . . .
N2 N 0.76144(10) 0.51050(9) 0.39555(10) 0.0224(5) Uani 1 1 d . . . . .
H2 H 0.762459 0.509017 0.348691 0.027 Uiso 1 1 calc R . . . .
N1 N 0.81547(10) 0.31427(10) 0.32019(10) 0.0260(5) Uani 1 1 d . . . . .
C7 C 0.77768(12) 0.35732(11) 0.35248(11) 0.0204(5) Uani 1 1 d . . . . .
C8 C 0.81545(12) 0.40671(11) 0.38875(11) 0.0209(5) Uani 1 1 d . . . . .
C14 C 0.78808(11) 0.46171(11) 0.43293(12) 0.0212(5) Uani 1 1 d . . . . .
C1 C 0.70569(12) 0.35121(11) 0.34668(12) 0.0227(5) Uani 1 1 d . . . . .
C9 C 0.87872(12) 0.39088(12) 0.37484(12) 0.0249(6) Uani 1 1 d . . . . .
C6 C 0.67825(12) 0.32280(11) 0.28449(13) 0.0257(6) Uani 1 1 d . . . . .
H6 H 0.705537 0.306916 0.247799 0.031 Uiso 1 1 calc R . . . .
C2 C 0.66359(12) 0.37433(12) 0.40133(12) 0.0274(6) Uani 1 1 d . . . . .
H2A H 0.681062 0.393008 0.443375 0.033 Uiso 1 1 calc R . . . .
C16 C 0.77876(13) 0.61712(12) 0.45763(13) 0.0295(6) Uani 1 1 d . . . . .
C15 C 0.73051(13) 0.56654(12) 0.43074(13) 0.0286(6) Uani 1 1 d . . . . .
H15A H 0.704609 0.551002 0.471674 0.034 Uiso 1 1 calc R . . . .
H15B H 0.700703 0.587258 0.396421 0.034 Uiso 1 1 calc R . . . .
C5 C 0.61093(13) 0.31811(13) 0.27703(14) 0.0327(6) Uani 1 1 d . . . . .
H5 H 0.593076 0.298839 0.235520 0.039 Uiso 1 1 calc R . . . .
C3 C 0.59648(13) 0.36958(13) 0.39320(14) 0.0336(6) Uani 1 1 d . . . . .
H3 H 0.568920 0.385090 0.429841 0.040 Uiso 1 1 calc R . . . .
C4 C 0.56973(13) 0.34202(13) 0.33120(14) 0.0357(7) Uani 1 1 d . . . . .
H4 H 0.524342 0.339472 0.325729 0.043 Uiso 1 1 calc R . . . .
C10 C 0.94452(14) 0.42011(15) 0.39197(15) 0.0411(7) Uani 1 1 d . U . . .
C17 C 0.82755(15) 0.64082(13) 0.41224(16) 0.0420(7) Uani 1 1 d . . . . .
H17 H 0.831951 0.623991 0.365332 0.050 Uiso 1 1 calc R . . . .
C21 C 0.77366(17) 0.64207(14) 0.52752(15) 0.0453(8) Uani 1 1 d . . . . .
H21 H 0.741194 0.626073 0.558518 0.054 Uiso 1 1 calc R . . . .
C18 C 0.86990(18) 0.68950(16) 0.4362(2) 0.0625(10) Uani 1 1 d . . . . .
H18 H 0.902697 0.705562 0.405726 0.075 Uiso 1 1 calc R . . . .
C20 C 0.8156(2) 0.68994(17) 0.5519(2) 0.0667(11) Uani 1 1 d . . . . .
H20 H 0.811764 0.705844 0.599279 0.080 Uiso 1 1 calc R . . . .
C13 C 0.93712(17) 0.48938(16) 0.4208(2) 0.0648(11) Uani 1 1 d . . . . .
H13A H 0.915283 0.516041 0.385020 0.097 Uiso 1 1 calc GR . . . .
H13B H 0.979792 0.507431 0.430832 0.097 Uiso 1 1 calc GR . . . .
H13C H 0.911606 0.488653 0.464831 0.097 Uiso 1 1 calc GR . . . .
C19 C 0.8628(2) 0.71420(17) 0.5069(3) 0.0730(13) Uani 1 1 d . . . . .
H19 H 0.890511 0.747448 0.523218 0.088 Uiso 1 1 calc R . . . .
C11 C 0.97672(18) 0.37893(19) 0.4521(2) 0.0780(11) Uani 1 1 d . U . . .
H11A H 0.949902 0.380289 0.495154 0.117 Uiso 1 1 calc GR . . . .
H11B H 1.019451 0.396446 0.462942 0.117 Uiso 1 1 calc GR . . . .
H11C H 0.980997 0.334255 0.435885 0.117 Uiso 1 1 calc GR . . . .
C12 C 0.9865(2) 0.4196(3) 0.3246(2) 0.1015(13) Uani 1 1 d . U . . .
H12A H 0.988928 0.375684 0.305613 0.152 Uiso 1 1 calc GR . . . .
H12B H 1.029910 0.434737 0.336485 0.152 Uiso 1 1 calc GR . . . .
H12C H 0.967505 0.448112 0.288544 0.152 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 N1 1.406(3) . ?
O1 C9 1.359(3) . ?
O2 C14 1.240(3) . ?
N2 H2 0.8600 . ?
N2 C14 1.322(3) . ?
N2 C15 1.453(3) . ?
N1 C7 1.307(3) . ?
C7 C8 1.429(3) . ?
C7 C1 1.473(3) . ?
C8 C14 1.489(3) . ?
C8 C9 1.351(3) . ?
C1 C6 1.395(3) . ?
C1 C2 1.399(3) . ?
C9 C10 1.498(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.379(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.376(4) . ?
C16 C15 1.505(4) . ?
C16 C17 1.382(4) . ?
C16 C21 1.382(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9300 . ?
C10 C13 1.512(4) . ?
C10 C11 1.532(5) . ?
C10 C12 1.502(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.369(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.397(6) . ?
C20 H20 0.9300 . ?
C20 C19 1.359(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C19 H19 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
C9 O1 N1 109.24(17) . . ?
C14 N2 H2 118.8 . . ?
C14 N2 C15 122.41(19) . . ?
C15 N2 H2 118.8 . . ?
C7 N1 O1 105.51(18) . . ?
N1 C7 C8 111.4(2) . . ?
N1 C7 C1 119.7(2) . . ?
C8 C7 C1 128.8(2) . . ?
C7 C8 C14 125.5(2) . . ?
C9 C8 C7 104.9(2) . . ?
C9 C8 C14 129.6(2) . . ?
O2 C14 N2 123.6(2) . . ?
O2 C14 C8 120.5(2) . . ?
N2 C14 C8 115.78(19) . . ?
C6 C1 C7 119.4(2) . . ?
C6 C1 C2 118.7(2) . . ?
C2 C1 C7 121.9(2) . . ?
O1 C9 C10 115.3(2) . . ?
C8 C9 O1 108.9(2) . . ?
C8 C9 C10 135.8(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2A 119.8 . . ?
C17 C16 C15 120.6(2) . . ?
C21 C16 C15 120.4(3) . . ?
C21 C16 C17 119.0(3) . . ?
N2 C15 C16 113.5(2) . . ?
N2 C15 H15A 108.9 . . ?
N2 C15 H15B 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C9 C10 C13 110.7(2) . . ?
C9 C10 C11 108.4(2) . . ?
C9 C10 C12 109.4(2) . . ?
C13 C10 C11 107.5(3) . . ?
C12 C10 C13 110.5(3) . . ?
C12 C10 C11 110.2(3) . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.1(3) . . ?
C20 C21 H21 119.4 . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.2(4) . . ?
C19 C18 H18 120.4 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 120.0(3) . . ?
C19 C20 H20 120.0 . . ?
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 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.853
