# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_20190408ZH_CZ_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1911441'
loop_
_audit_author_name
_audit_author_address
'Song Sun'
;Changzhou University
China
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N2 O'
_chemical_formula_weight         354.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   28.608(3)
_cell_length_b                   28.608(3)
_cell_length_c                   11.5472(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8184.6(18)
_cell_formula_units_Z            18
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    7973
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      53.77

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             3384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.395
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12049
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.687
_diffrn_reflns_theta_max         52.986
_diffrn_reflns_theta_full        52.986
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3188
_reflns_number_gt                2465
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1082P)²+5.9995P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3188
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1796
_refine_ls_wR_factor_gt          0.1626
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
O001 O 0.44337(6) 0.27033(6) 0.54559(12) 0.0530(4) Uani 1 1 d . . . . .
N002 N 0.49223(7) 0.33028(7) 0.40721(14) 0.0498(5) Uani 1 1 d . . . . .
N003 N 0.54241(7) 0.38561(7) 0.25972(15) 0.0544(5) Uani 1 1 d . . . . .
H1 H 0.558224 0.422894 0.222552 0.065 Uiso 1 1 d R U . . .
C004 C 0.48168(9) 0.40788(9) 0.36449(16) 0.0479(5) Uani 1 1 d . . . . .
C005 C 0.42039(8) 0.33801(8) 0.50191(17) 0.0488(5) Uani 1 1 d . . . . .
C006 C 0.43847(8) 0.38946(8) 0.44635(17) 0.0477(5) Uani 1 1 d . . . . .
C007 C 0.45182(8) 0.31527(8) 0.48485(17) 0.0487(5) Uani 1 1 d . . . . .
C008 C 0.50013(9) 0.45681(9) 0.30897(17) 0.0501(5) Uani 1 1 d . . . . .
H008 H 0.528255 0.468099 0.253460 0.060 Uiso 1 1 calc R U . . .
C009 C 0.41856(9) 0.42372(8) 0.47302(17) 0.0501(5) Uani 1 1 d . . . . .
H009 H 0.391257 0.412884 0.530353 0.060 Uiso 1 1 calc R U . . .
C00A C 0.50536(8) 0.37371(9) 0.34435(17) 0.0488(5) Uani 1 1 d . . . . .
C00B C 0.36860(9) 0.30477(8) 0.56181(17) 0.0503(5) Uani 1 1 d . . . . .
C00C C 0.41730(9) 0.26516(10) 0.65622(18) 0.0556(6) Uani 1 1 d . . . . .
H00A H 0.441431 0.295556 0.707289 0.067 Uiso 1 1 calc R U . . .
H00B H 0.409835 0.231099 0.694255 0.067 Uiso 1 1 calc R U . . .
C00D C 0.43740(9) 0.47347(8) 0.41828(17) 0.0489(5) Uani 1 1 d . . . . .
C00E C 0.47849(9) 0.49015(8) 0.33237(17) 0.0490(5) Uani 1 1 d . . . . .
C00F C 0.32090(9) 0.30493(9) 0.53688(18) 0.0542(6) Uani 1 1 d . . . . .
H00F H 0.321531 0.330692 0.484034 0.065 Uiso 1 1 calc R U . . .
C00G C 0.36583(9) 0.26529(9) 0.63804(17) 0.0512(5) Uani 1 1 d . . . . .
C00H C 0.41697(9) 0.50865(9) 0.44390(19) 0.0548(6) Uani 1 1 d . . . . .
H00H H 0.390482 0.499078 0.502674 0.066 Uiso 1 1 calc R U . . .
C00I C 0.56771(9) 0.35286(9) 0.24302(19) 0.0545(6) Uani 1 1 d . . . . .
H00C H 0.539664 0.315231 0.225472 0.065 Uiso 1 1 calc R U . . .
H00D H 0.586234 0.352604 0.315235 0.065 Uiso 1 1 calc R U . . .
C00J C 0.60829(9) 0.37491(10) 0.1444(2) 0.0583(6) Uani 1 1 d . . . . .
H00E H 0.636175 0.412390 0.163627 0.070 Uiso 1 1 calc R U . . .
H00G H 0.626460 0.353246 0.139279 0.070 Uiso 1 1 calc R U . . .
C00K C 0.27275(10) 0.26792(9) 0.58845(19) 0.0579(6) Uani 1 1 d . . . . .
H00K H 0.240673 0.268615 0.570736 0.069 Uiso 1 1 calc R U . . .
C00L C 0.31737(10) 0.22826(9) 0.68890(19) 0.0581(6) Uani 1 1 d . . . . .
H00L H 0.316145 0.201649 0.740010 0.070 Uiso 1 1 calc R U . . .
C00M C 0.49641(9) 0.53992(9) 0.27355(18) 0.0555(6) Uani 1 1 d . . . . .
H00M H 0.523838 0.551232 0.216369 0.067 Uiso 1 1 calc R U . . .
C00N C 0.43497(10) 0.55575(9) 0.3852(2) 0.0576(6) Uani 1 1 d . . . . .
H00N H 0.420552 0.578465 0.402934 0.069 Uiso 1 1 calc R U . . .
C00O C 0.27072(10) 0.22986(9) 0.6656(2) 0.0610(6) Uani 1 1 d . . . . .
H00O H 0.237688 0.205139 0.702065 0.073 Uiso 1 1 calc R U . . .
C00P C 0.47464(9) 0.57143(9) 0.2985(2) 0.0584(6) Uani 1 1 d . . . . .
H00P H 0.486203 0.604149 0.257233 0.070 Uiso 1 1 calc R U . . .
C00Q C 0.58483(10) 0.37499(10) 0.0259(2) 0.0640(6) Uani 1 1 d . . . . .
H00I H 0.563223 0.393197 0.031677 0.077 Uiso 1 1 calc R U . . .
H00J H 0.560525 0.337312 0.000782 0.077 Uiso 1 1 calc R U . . .
C00R C 0.62920(12) 0.40380(12) -0.0637(2) 0.0810(8) Uani 1 1 d . . . . .
H00Q H 0.653170 0.441167 -0.039152 0.122 Uiso 1 1 calc R U . . .
H00R H 0.613005 0.403565 -0.138633 0.122 Uiso 1 1 calc R U . . .
H00S H 0.650006 0.385215 -0.071035 0.122 Uiso 1 1 calc R U . . .


_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
O001 C007 1.376(2) . ?
O001 C00C 1.449(2) . ?
N002 C00A 1.321(3) . ?
N002 C007 1.352(3) . ?
N003 C00A 1.354(3) . ?
N003 C00I 1.455(3) . ?
N003 H1 1.0218 . ?
C004 C008 1.382(3) . ?
C004 C006 1.431(3) . ?
C004 C00A 1.460(3) . ?
C005 C007 1.362(3) . ?
C005 C006 1.444(3) . ?
C005 C00B 1.473(3) . ?
C006 C009 1.392(3) . ?
C008 C00E 1.399(3) . ?
C008 H008 0.9500 . ?
C009 C00D 1.396(3) . ?
C009 H009 0.9500 . ?
C00B C00F 1.397(3) . ?
C00B C00G 1.403(3) . ?
C00C C00G 1.489(3) . ?
C00C H00A 0.9900 . ?
C00C H00B 0.9900 . ?
C00D C00H 1.425(3) . ?
C00D C00E 1.426(3) . ?
C00E C00M 1.422(3) . ?
C00F C00K 1.384(3) . ?
C00F H00F 0.9500 . ?
C00G C00L 1.386(3) . ?
C00H C00N 1.359(3) . ?
C00H H00H 0.9500 . ?
C00I C00J 1.520(3) . ?
C00I H00C 0.9900 . ?
C00I H00D 0.9900 . ?
C00J C00Q 1.524(3) . ?
C00J H00E 0.9900 . ?
C00J H00G 0.9900 . ?
C00K C00O 1.385(3) . ?
C00K H00K 0.9500 . ?
C00L C00O 1.384(3) . ?
C00L H00L 0.9500 . ?
C00M C00P 1.358(3) . ?
C00M H00M 0.9500 . ?
C00N C00P 1.408(3) . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00Q C00R 1.522(3) . ?
C00Q H00I 0.9900 . ?
C00Q H00J 0.9900 . ?
C00R H00Q 0.9800 . ?
C00R H00R 0.9800 . ?
C00R H00S 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
C007 O001 C00C 112.69(15) . . ?
C00A N002 C007 117.32(18) . . ?
C00A N003 C00I 120.85(18) . . ?
C00A N003 H1 116.6 . . ?
C00I N003 H1 120.9 . . ?
C008 C004 C006 120.10(19) . . ?
C008 C004 C00A 122.28(19) . . ?
C006 C004 C00A 117.61(18) . . ?
C007 C005 C006 115.92(19) . . ?
C007 C005 C00B 116.79(19) . . ?
C006 C005 C00B 126.79(19) . . ?
C009 C006 C004 117.98(19) . . ?
C009 C006 C005 123.73(19) . . ?
C004 C006 C005 118.17(18) . . ?
C005 C007 N002 127.45(19) . . ?
C005 C007 O001 121.54(18) . . ?
N002 C007 O001 110.95(17) . . ?
C004 C008 C00E 121.72(19) . . ?
C004 C008 H008 119.1 . . ?
C00E C008 H008 119.1 . . ?
C00D C009 C006 122.17(19) . . ?
C00D C009 H009 118.9 . . ?
C006 C009 H009 118.9 . . ?
N002 C00A N003 116.85(19) . . ?
N002 C00A C004 122.23(18) . . ?
N003 C00A C004 120.91(19) . . ?
C00F C00B C00G 118.0(2) . . ?
C00F C00B C005 124.76(19) . . ?
C00G C00B C005 116.62(19) . . ?
O001 C00C C00G 109.55(17) . . ?
O001 C00C H00A 109.8 . . ?
C00G C00C H00A 109.8 . . ?
O001 C00C H00B 109.8 . . ?
C00G C00C H00B 109.8 . . ?
H00A C00C H00B 108.2 . . ?
C009 C00D C00H 122.7(2) . . ?
C009 C00D C00E 119.32(19) . . ?
C00H C00D C00E 117.95(19) . . ?
C008 C00E C00M 122.0(2) . . ?
C008 C00E C00D 118.56(19) . . ?
C00M C00E C00D 119.5(2) . . ?
C00K C00F C00B 120.6(2) . . ?
C00K C00F H00F 119.7 . . ?
C00B C00F H00F 119.7 . . ?
C00L C00G C00B 120.9(2) . . ?
C00L C00G C00C 123.4(2) . . ?
C00B C00G C00C 115.64(19) . . ?
C00N C00H C00D 120.7(2) . . ?
C00N C00H H00H 119.6 . . ?
C00D C00H H00H 119.6 . . ?
N003 C00I C00J 110.78(18) . . ?
N003 C00I H00C 109.5 . . ?
C00J C00I H00C 109.5 . . ?
N003 C00I H00D 109.5 . . ?
C00J C00I H00D 109.5 . . ?
H00C C00I H00D 108.1 . . ?
C00Q C00J C00I 115.32(19) . . ?
C00Q C00J H00E 108.4 . . ?
C00I C00J H00E 108.4 . . ?
C00Q C00J H00G 108.4 . . ?
C00I C00J H00G 108.4 . . ?
H00E C00J H00G 107.5 . . ?
C00O C00K C00F 120.8(2) . . ?
C00O C00K H00K 119.6 . . ?
C00F C00K H00K 119.6 . . ?
C00G C00L C00O 120.3(2) . . ?
C00G C00L H00L 119.8 . . ?
C00O C00L H00L 119.8 . . ?
C00P C00M C00E 120.5(2) . . ?
C00P C00M H00M 119.7 . . ?
C00E C00M H00M 119.7 . . ?
C00H C00N C00P 121.1(2) . . ?
C00H C00N H00N 119.5 . . ?
C00P C00N H00N 119.5 . . ?
C00L C00O C00K 119.3(2) . . ?
C00L C00O H00O 120.4 . . ?
C00K C00O H00O 120.4 . . ?
C00M C00P C00N 120.2(2) . . ?
C00M C00P H00P 119.9 . . ?
C00N C00P H00P 119.9 . . ?
C00J C00Q C00R 111.3(2) . . ?
C00J C00Q H00I 109.4 . . ?
C00R C00Q H00I 109.4 . . ?
C00J C00Q H00J 109.4 . . ?
C00R C00Q H00J 109.4 . . ?
H00I C00Q H00J 108.0 . . ?
C00Q C00R H00Q 109.5 . . ?
C00Q C00R H00R 109.5 . . ?
H00Q C00R H00R 109.5 . . ?
C00Q C00R H00S 109.5 . . ?
H00Q C00R H00S 109.5 . . ?
H00R C00R H00S 109.5 . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.044

