# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_mo_ddz20132_0m
_database_code_depnum_ccdc_archive 'CCDC 2089256'
loop_
_audit_author_name
_audit_author_address
'Zhuo-Ya Mao'
;fudan university
China
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H28 N2 O4'
_chemical_formula_weight         312.40

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.6865(7)
_cell_length_b                   10.3400(8)
_cell_length_c                   17.7546(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1778.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3986
_cell_measurement_theta_min      4.859
_cell_measurement_theta_max      49.132

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6306
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            8722
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.294
_diffrn_reflns_theta_max         25.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3456
_reflns_number_gt                2750
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.992

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0395P)²+0.1273P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.043(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 960 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.0(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3456
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
O1 O 0.4807(2) -0.02115(17) 0.14469(11) 0.0737(6) Uani 1 1 d . . . . .
H1 H 0.5481 -0.0104 0.1720 0.111 Uiso 1 1 calc R U . . .
O2 O 0.6627(2) 0.05584(17) 0.25262(9) 0.0668(5) Uani 1 1 d . . . . .
O3 O 0.7742(2) 0.31272(19) 0.05517(10) 0.0729(6) Uani 1 1 d . . . . .
O4 O 0.78305(18) 0.35528(18) 0.18108(9) 0.0631(5) Uani 1 1 d . . . . .
N1 N 0.6094(2) 0.24300(19) 0.13541(10) 0.0517(5) Uani 1 1 d . . . . .
N2 N 0.6243(2) 0.21572(19) 0.33627(10) 0.0518(5) Uani 1 1 d . . . . .
H2 H 0.5992 0.2949 0.3419 0.062 Uiso 1 1 calc R U . . .
C1 C 0.5266(3) 0.1781(3) 0.07796(14) 0.0607(7) Uani 1 1 d . . . . .
H1A H 0.5832 0.1222 0.0468 0.073 Uiso 1 1 calc R U . . .
H1B H 0.4795 0.2403 0.0461 0.073 Uiso 1 1 calc R U . . .
C2 C 0.4253(3) 0.1010(3) 0.12391(16) 0.0658(7) Uani 1 1 d . . . . .
H2A H 0.3390 0.0893 0.0959 0.079 Uiso 1 1 calc R U . . .
C3 C 0.4014(3) 0.1882(3) 0.19171(15) 0.0665(7) Uani 1 1 d . . . . .
H3A H 0.3671 0.1387 0.2342 0.080 Uiso 1 1 calc R U . . .
H3B H 0.3354 0.2557 0.1798 0.080 Uiso 1 1 calc R U . . .
C4 C 0.5436(2) 0.2460(2) 0.20930(12) 0.0483(6) Uani 1 1 d . . . . .
H4 H 0.5341 0.3354 0.2269 0.058 Uiso 1 1 calc R U . . .
C5 C 0.6184(2) 0.1648(2) 0.26767(12) 0.0486(6) Uani 1 1 d . . . . .
C6 C 0.6706(3) 0.1450(2) 0.40256(12) 0.0509(6) Uani 1 1 d . . . . .
H6 H 0.7460 0.0875 0.3874 0.061 Uiso 1 1 calc R U . . .
C7 C 0.7255(3) 0.2383(3) 0.46063(13) 0.0660(7) Uani 1 1 d . . . . .
H7A H 0.6544 0.3007 0.4732 0.079 Uiso 1 1 calc R U . . .
H7B H 0.8035 0.2850 0.4398 0.079 Uiso 1 1 calc R U . . .
C8 C 0.7705(3) 0.1678(3) 0.53142(15) 0.0746(8) Uani 1 1 d . . . . .
H8A H 0.8492 0.1133 0.5198 0.089 Uiso 1 1 calc R U . . .
H8B H 0.7994 0.2305 0.5688 0.089 Uiso 1 1 calc R U . . .
C9 C 0.6569(4) 0.0858(3) 0.56357(15) 0.0768(9) Uani 1 1 d . . . . .
H9A H 0.5831 0.1413 0.5815 0.092 Uiso 1 1 calc R U . . .
H9B H 0.6921 0.0372 0.6062 0.092 Uiso 1 1 calc R U . . .
C10 C 0.6003(3) -0.0065(3) 0.50598(15) 0.0761(8) Uani 1 1 d . . . . .
H10A H 0.5217 -0.0519 0.5271 0.091 Uiso 1 1 calc R U . . .
H10B H 0.6703 -0.0701 0.4936 0.091 Uiso 1 1 calc R U . . .
C11 C 0.5559(3) 0.0632(3) 0.43477(15) 0.0635(7) Uani 1 1 d . . . . .
H11A H 0.5274 0.0000 0.3975 0.076 Uiso 1 1 calc R U . . .
H11B H 0.4772 0.1179 0.4459 0.076 Uiso 1 1 calc R U . . .
C12 C 0.7275(3) 0.3048(2) 0.11808(14) 0.0547(6) Uani 1 1 d . . . . .
C13 C 0.9173(3) 0.4211(3) 0.17972(16) 0.0650(7) Uani 1 1 d . . . . .
C14 C 1.0284(3) 0.3309(3) 0.1510(2) 0.0977(11) Uani 1 1 d . . . . .
H14A H 1.0244 0.2508 0.1783 0.147 Uiso 1 1 calc R U . . .
H14B H 1.1173 0.3700 0.1581 0.147 Uiso 1 1 calc R U . . .
H14C H 1.0140 0.3145 0.0983 0.147 Uiso 1 1 calc R U . . .
C15 C 0.9076(4) 0.5417(3) 0.1330(2) 0.0975(11) Uani 1 1 d . . . . .
H15A H 0.8988 0.5187 0.0808 0.146 Uiso 1 1 calc R U . . .
H15B H 0.9895 0.5927 0.1399 0.146 Uiso 1 1 calc R U . . .
H15C H 0.8284 0.5909 0.1483 0.146 Uiso 1 1 calc R U . . .
C16 C 0.9387(4) 0.4531(4) 0.26174(18) 0.0978(11) Uani 1 1 d . . . . .
H16A H 0.8633 0.5053 0.2793 0.147 Uiso 1 1 calc R U . . .
H16B H 1.0236 0.4999 0.2676 0.147 Uiso 1 1 calc R U . . .
H16C H 0.9427 0.3746 0.2905 0.147 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
O1 C2 1.421(3) . ?
O1 H1 0.8200 . ?
O2 C5 1.235(3) . ?
O3 C12 1.208(3) . ?
O4 C12 1.347(3) . ?
O4 C13 1.468(3) . ?
N1 C12 1.346(3) . ?
N1 C4 1.459(3) . ?
N1 C1 1.461(3) . ?
N2 C5 1.328(3) . ?
N2 C6 1.456(3) . ?
N2 H2 0.8600 . ?
C1 C2 1.505(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.522(4) . ?
C2 H2A 0.9800 . ?
C3 C4 1.534(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.518(3) . ?
C4 H4 0.9800 . ?
C6 C7 1.508(3) . ?
C6 C11 1.509(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.517(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.502(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.502(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.517(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 C15 1.502(4) . ?
C13 C16 1.508(4) . ?
C13 C14 1.513(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C2 O1 H1 109.5 . . ?
C12 O4 C13 121.3(2) . . ?
C12 N1 C4 124.5(2) . . ?
C12 N1 C1 121.7(2) . . ?
C4 N1 C1 113.5(2) . . ?
C5 N2 C6 123.75(19) . . ?
C5 N2 H2 118.1 . . ?
C6 N2 H2 118.1 . . ?
N1 C1 C2 102.88(19) . . ?
N1 C1 H1A 111.2 . . ?
C2 C1 H1A 111.2 . . ?
N1 C1 H1B 111.2 . . ?
C2 C1 H1B 111.2 . . ?
H1A C1 H1B 109.1 . . ?
O1 C2 C1 111.4(2) . . ?
O1 C2 C3 112.3(2) . . ?
C1 C2 C3 102.3(2) . . ?
O1 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
C3 C2 H2A 110.2 . . ?
C2 C3 C4 104.8(2) . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
N1 C4 C5 113.19(19) . . ?
N1 C4 C3 101.58(19) . . ?
C5 C4 C3 110.6(2) . . ?
N1 C4 H4 110.4 . . ?
C5 C4 H4 110.4 . . ?
C3 C4 H4 110.4 . . ?
O2 C5 N2 123.0(2) . . ?
O2 C5 C4 121.5(2) . . ?
N2 C5 C4 115.3(2) . . ?
N2 C6 C7 109.90(19) . . ?
N2 C6 C11 111.16(19) . . ?
C7 C6 C11 111.1(2) . . ?
N2 C6 H6 108.2 . . ?
C7 C6 H6 108.2 . . ?
C11 C6 H6 108.2 . . ?
C6 C7 C8 111.1(2) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C7 112.1(3) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 111.5(2) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 111.7(2) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C6 C11 C10 111.9(2) . . ?
C6 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C6 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
O3 C12 N1 124.2(2) . . ?
O3 C12 O4 126.3(2) . . ?
N1 C12 O4 109.5(2) . . ?
O4 C13 C15 109.8(2) . . ?
O4 C13 C16 102.0(2) . . ?
C15 C13 C16 111.1(3) . . ?
O4 C13 C14 110.5(2) . . ?
C15 C13 C14 111.7(3) . . ?
C16 C13 C14 111.3(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C12 N1 C1 C2 168.4(2) . . . . ?
C4 N1 C1 C2 -18.2(3) . . . . ?
N1 C1 C2 O1 -86.1(3) . . . . ?
N1 C1 C2 C3 34.1(3) . . . . ?
O1 C2 C3 C4 80.8(3) . . . . ?
C1 C2 C3 C4 -38.8(3) . . . . ?
C12 N1 C4 C5 -73.9(3) . . . . ?
C1 N1 C4 C5 112.9(2) . . . . ?
C12 N1 C4 C3 167.5(2) . . . . ?
C1 N1 C4 C3 -5.7(3) . . . . ?
C2 C3 C4 N1 27.3(2) . . . . ?
C2 C3 C4 C5 -93.2(2) . . . . ?
C6 N2 C5 O2 -6.2(4) . . . . ?
C6 N2 C5 C4 169.5(2) . . . . ?
N1 C4 C5 O2 -43.2(3) . . . . ?
C3 C4 C5 O2 70.1(3) . . . . ?
N1 C4 C5 N2 141.1(2) . . . . ?
C3 C4 C5 N2 -105.7(2) . . . . ?
C5 N2 C6 C7 154.5(2) . . . . ?
C5 N2 C6 C11 -82.1(3) . . . . ?
N2 C6 C7 C8 178.2(2) . . . . ?
C11 C6 C7 C8 54.8(3) . . . . ?
C6 C7 C8 C9 -55.1(3) . . . . ?
C7 C8 C9 C10 54.4(3) . . . . ?
C8 C9 C10 C11 -53.6(3) . . . . ?
N2 C6 C11 C10 -177.4(2) . . . . ?
C7 C6 C11 C10 -54.7(3) . . . . ?
C9 C10 C11 C6 54.1(3) . . . . ?
C4 N1 C12 O3 -172.3(3) . . . . ?
C1 N1 C12 O3 0.4(4) . . . . ?
C4 N1 C12 O4 7.5(3) . . . . ?
C1 N1 C12 O4 -179.8(2) . . . . ?
C13 O4 C12 O3 -4.2(4) . . . . ?
C13 O4 C12 N1 176.0(2) . . . . ?
C12 O4 C13 C15 65.1(3) . . . . ?
C12 O4 C13 C16 -177.0(2) . . . . ?
C12 O4 C13 C14 -58.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15A O3 0.96 2.49 3.031(4) 115.5 .
C14 H14C O3 0.96 2.45 2.999(4) 116.4 .
N2 H2 O1 0.86 2.07 2.924(3) 174.4 3_655
O1 H1 O2 0.82 1.94 2.723(3) 160.1 .
O1 H1 O2 0.82 1.94 2.723(3) 160.1 .
N2 H2 O1 0.86 2.07 2.924(3) 174.4 3_655
C14 H14C O3 0.96 2.45 2.999(4) 116.4 .
C15 H15A O3 0.96 2.49 3.031(4) 115.5 .

_refine_diff_density_max         0.087
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.023

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_d8v21545_0m
_database_code_depnum_ccdc_archive 'CCDC 2094460'
loop_
_audit_author_name
_audit_author_address
'Zhuo-Ya Mao'
;fudan university
China
;
_audit_update_record             
;
2021-07-05 deposited with the CCDC.	2021-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 Cl2 N2 O'
_chemical_formula_weight         317.24

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   6.0632(3)
_cell_length_b                   26.8654(12)
_cell_length_c                   10.3001(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.299(2)
_cell_angle_gamma                90
_cell_volume                     1676.44(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    3801
_cell_measurement_theta_min      4.986
_cell_measurement_theta_max      54.953

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.385
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6686
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            12631
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.015
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3288
_reflns_number_gt                2451
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0291P)²+0.9865P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3288
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
Cl1 Cl 0.23839(14) 0.52922(3) 0.33490(7) 0.0555(2) Uani 1 1 d . . . . .
O1 O 0.6731(3) 0.18802(7) 0.54546(16) 0.0414(5) Uani 1 1 d . . . . .
N1 N 0.4033(3) 0.16462(7) 0.39687(19) 0.0336(5) Uani 1 1 d . . . . .
H1 H 0.3407 0.1728 0.3224 0.040 Uiso 1 1 calc R U . . .
N2 N 0.8377(3) 0.25702(7) 0.38583(18) 0.0290(5) Uani 1 1 d . . . . .
H2A H 0.8890 0.2479 0.4741 0.035 Uiso 1 1 calc R U . . .
H2B H 0.9366 0.2419 0.3240 0.035 Uiso 1 1 calc R U . . .
C1 C 0.5636(4) 0.19433(9) 0.4432(2) 0.0306(5) Uani 1 1 d . . . . .
C2 C 0.6056(4) 0.23965(9) 0.3597(2) 0.0280(5) Uani 1 1 d . . . . .
H2 H 0.5827 0.2310 0.2667 0.034 Uiso 1 1 calc R U . . .
C3 C 0.4625(4) 0.28495(9) 0.3929(2) 0.0321(6) Uani 1 1 d . . . . .
H3A H 0.3619 0.2765 0.4617 0.039 Uiso 1 1 calc R U . . .
H3B H 0.3751 0.2960 0.3162 0.039 Uiso 1 1 calc R U . . .
C4 C 0.6251(4) 0.32598(9) 0.4390(2) 0.0287(5) Uani 1 1 d . . . . .
H4 H 0.6545 0.3217 0.5336 0.034 Uiso 1 1 calc R U . . .
C5 C 0.8337(4) 0.31196(9) 0.3705(2) 0.0303(5) Uani 1 1 d . . . . .
H5A H 0.8240 0.3216 0.2787 0.036 Uiso 1 1 calc R U . . .
H5B H 0.9645 0.3274 0.4124 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5391(4) 0.37804(9) 0.4162(2) 0.0289(5) Uani 1 1 d . . . . .
C7 C 0.3429(4) 0.39228(9) 0.4708(2) 0.0337(6) Uani 1 1 d . . . . .
H7 H 0.2710 0.3698 0.5248 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2513(4) 0.43851(10) 0.4479(2) 0.0395(6) Uani 1 1 d . . . . .
H8 H 0.1182 0.4475 0.4853 0.047 Uiso 1 1 calc R U . . .
C9 C 0.3580(4) 0.47137(9) 0.3691(2) 0.0373(6) Uani 1 1 d . . . . .
C10 C 0.5561(5) 0.45928(10) 0.3170(2) 0.0399(6) Uani 1 1 d . . . . .
H10 H 0.6301 0.4825 0.2660 0.048 Uiso 1 1 calc R U . . .
C11 C 0.6452(4) 0.41262(9) 0.3402(2) 0.0359(6) Uani 1 1 d . . . . .
H11 H 0.7800 0.4041 0.3040 0.043 Uiso 1 1 calc R U . . .
C12 C 0.3207(4) 0.11888(9) 0.4596(2) 0.0375(6) Uani 1 1 d . . . . .
C13 C 0.2192(5) 0.13188(11) 0.5877(3) 0.0488(7) Uani 1 1 d . . . . .
H13A H 0.3318 0.1457 0.6467 0.073 Uiso 1 1 calc R U . . .
H13B H 0.1586 0.1021 0.6256 0.073 Uiso 1 1 calc R U . . .
H13C H 0.1025 0.1561 0.5725 0.073 Uiso 1 1 calc R U . . .
C14 C 0.1452(6) 0.09728(12) 0.3653(3) 0.0659(10) Uani 1 1 d . . . . .
H14A H 0.0288 0.1216 0.3496 0.099 Uiso 1 1 calc R U . . .
H14B H 0.0836 0.0674 0.4023 0.099 Uiso 1 1 calc R U . . .
H14C H 0.2116 0.0891 0.2838 0.099 Uiso 1 1 calc R U . . .
C15 C 0.5099(5) 0.08190(10) 0.4798(3) 0.0504(8) Uani 1 1 d . . . . .
H15A H 0.5713 0.0741 0.3967 0.076 Uiso 1 1 calc R U . . .
H15B H 0.4550 0.0517 0.5186 0.076 Uiso 1 1 calc R U . . .
H15C H 0.6236 0.0964 0.5370 0.076 Uiso 1 1 calc R U . . .
Cl2 Cl 0.09571(10) 0.21598(3) 0.16251(5) 0.03806(18) Uani 1 1 d . . . . .


_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
Cl1 C9 1.745(3) . ?
O1 C1 1.234(3) . ?
N1 C1 1.332(3) . ?
N1 C12 1.485(3) . ?
N1 H1 0.8700 . ?
N2 C5 1.484(3) . ?
N2 C2 1.497(3) . ?
N2 H2A 0.9800 . ?
N2 H2B 0.9800 . ?
C1 C2 1.518(3) . ?
C2 C3 1.541(3) . ?
C2 H2 0.9900 . ?
C3 C4 1.541(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 C6 1.508(3) . ?
C4 C5 1.520(3) . ?
C4 H4 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C7 1.390(3) . ?
C6 C11 1.389(3) . ?
C7 C8 1.377(3) . ?
C7 H7 0.9400 . ?
C8 C9 1.378(4) . ?
C8 H8 0.9400 . ?
C9 C10 1.374(4) . ?
C10 C11 1.382(4) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C12 C13 1.518(4) . ?
C12 C15 1.525(4) . ?
C12 C14 1.527(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?

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
C1 N1 C12 126.4(2) . . ?
C1 N1 H1 116.8 . . ?
C12 N1 H1 116.8 . . ?
C5 N2 C2 106.23(17) . . ?
C5 N2 H2A 110.5 . . ?
C2 N2 H2A 110.5 . . ?
C5 N2 H2B 110.5 . . ?
C2 N2 H2B 110.5 . . ?
H2A N2 H2B 108.7 . . ?
O1 C1 N1 125.7(2) . . ?
O1 C1 C2 119.8(2) . . ?
N1 C1 C2 114.5(2) . . ?
N2 C2 C1 109.03(18) . . ?
N2 C2 C3 104.33(18) . . ?
C1 C2 C3 113.52(19) . . ?
N2 C2 H2 109.9 . . ?
C1 C2 H2 109.9 . . ?
C3 C2 H2 109.9 . . ?
C2 C3 C4 105.93(18) . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C4 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C6 C4 C5 116.5(2) . . ?
C6 C4 C3 113.73(19) . . ?
C5 C4 C3 102.33(18) . . ?
C6 C4 H4 107.9 . . ?
C5 C4 H4 107.9 . . ?
C3 C4 H4 107.9 . . ?
N2 C5 C4 101.97(18) . . ?
N2 C5 H5A 111.4 . . ?
C4 C5 H5A 111.4 . . ?
N2 C5 H5B 111.4 . . ?
C4 C5 H5B 111.4 . . ?
H5A C5 H5B 109.2 . . ?
C7 C6 C11 117.9(2) . . ?
C7 C6 C4 119.2(2) . . ?
C11 C6 C4 122.9(2) . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 118.9(2) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 Cl1 119.6(2) . . ?
C8 C9 Cl1 119.2(2) . . ?
C9 C10 C11 119.2(2) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C6 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
N1 C12 C13 110.1(2) . . ?
N1 C12 C15 109.5(2) . . ?
C13 C12 C15 111.1(2) . . ?
N1 C12 C14 106.0(2) . . ?
C13 C12 C14 110.1(2) . . ?
C15 C12 C14 109.9(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C12 N1 C1 O1 1.5(4) . . . . ?
C12 N1 C1 C2 -177.6(2) . . . . ?
C5 N2 C2 C1 -147.34(18) . . . . ?
C5 N2 C2 C3 -25.8(2) . . . . ?
O1 C1 C2 N2 25.2(3) . . . . ?
N1 C1 C2 N2 -155.7(2) . . . . ?
O1 C1 C2 C3 -90.7(3) . . . . ?
N1 C1 C2 C3 88.5(3) . . . . ?
N2 C2 C3 C4 -0.9(2) . . . . ?
C1 C2 C3 C4 117.7(2) . . . . ?
C2 C3 C4 C6 152.64(19) . . . . ?
C2 C3 C4 C5 26.1(2) . . . . ?
C2 N2 C5 C4 42.6(2) . . . . ?
C6 C4 C5 N2 -166.27(18) . . . . ?
C3 C4 C5 N2 -41.6(2) . . . . ?
C5 C4 C6 C7 176.8(2) . . . . ?
C3 C4 C6 C7 58.1(3) . . . . ?
C5 C4 C6 C11 -1.9(3) . . . . ?
C3 C4 C6 C11 -120.6(2) . . . . ?
C11 C6 C7 C8 2.0(4) . . . . ?
C4 C6 C7 C8 -176.7(2) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C7 C8 C9 C10 -2.0(4) . . . . ?
C7 C8 C9 Cl1 177.81(19) . . . . ?
C8 C9 C10 C11 2.4(4) . . . . ?
Cl1 C9 C10 C11 -177.40(19) . . . . ?
C9 C10 C11 C6 -0.6(4) . . . . ?
C7 C6 C11 C10 -1.6(4) . . . . ?
C4 C6 C11 C10 177.1(2) . . . . ?
C1 N1 C12 C13 63.4(3) . . . . ?
C1 N1 C12 C15 -59.0(3) . . . . ?
C1 N1 C12 C14 -177.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15C O1 0.97 2.48 3.084(3) 120.1 .
C15 H15A Cl1 0.97 2.95 3.904(3) 168.1 2_645
C13 H13A O1 0.97 2.61 3.183(3) 117.7 .
C8 H8 Cl1 0.94 2.97 3.886(3) 165.6 3_566
C5 H5B Cl2 0.98 2.91 3.428(2) 114.1 4_666
C5 H5A O1 0.98 2.55 3.449(3) 152.7 4_565
C3 H3A Cl2 0.98 2.68 3.627(2) 162.2 4_566
N2 H2B Cl2 0.98 2.08 3.040(2) 167.3 1_655
N2 H2A Cl2 0.98 2.47 3.2768(19) 139.8 4_666
N1 H1 Cl2 0.87 2.46 3.294(2) 159.8 .

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_d8v21544_0m
_database_code_depnum_ccdc_archive 'CCDC 2094462'
loop_
_audit_author_name
_audit_author_address
'Zhuo-Ya Mao'
;fudan university
China
;
_audit_update_record             
;
2021-07-05 deposited with the CCDC.	2021-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H15 Br Cl F N2 O'
_chemical_formula_weight         337.62

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

_cell_length_a                   6.5060(4)
_cell_length_b                   4.7861(3)
_cell_length_c                   21.3358(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.991(2)
_cell_angle_gamma                90
_cell_volume                     659.42(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    5647
_cell_measurement_theta_min      5.771
_cell_measurement_theta_max      55.026

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.321
_shelx_estimated_absorpt_T_min   0.602
_shelx_estimated_absorpt_T_max   0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4967
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            6384
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.886
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             2446
_reflns_number_gt                2373
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_max     0.913
_reflns_Friedel_fraction_full    0.913

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 963 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.030(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2446
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0195
_refine_ls_wR_factor_ref         0.0490
_refine_ls_wR_factor_gt          0.0487
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.002
_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
Br1 Br 1.36307(5) -0.01468(9) 0.94597(2) 0.03374(13) Uani 1 1 d . . . . .
Cl1 Cl 0.86958(11) 0.21716(14) 0.65298(3) 0.02710(18) Uani 1 1 d . . . . .
F1 F 0.2956(3) 0.3616(4) 0.53155(9) 0.0329(5) Uani 1 1 d . . . . .
O1 O 0.4009(3) 1.0159(5) 0.72462(8) 0.0246(5) Uani 1 1 d . . . . .
N1 N 0.6396(4) 0.6742(5) 0.74538(10) 0.0225(5) Uani 1 1 d . . . . .
H1 H 0.6803 0.5101 0.7344 0.027 Uiso 1 1 calc R U . . .
N2 N 0.1618(4) 0.7010(5) 0.63907(10) 0.0186(5) Uani 1 1 d . . . . .
C1 C 0.1112(4) 0.7408(8) 0.56901(12) 0.0249(6) Uani 1 1 d . . . . .
H1A H 0.0779 0.9366 0.5589 0.030 Uiso 1 1 calc R U . . .
H1B H -0.0068 0.6241 0.5524 0.030 Uiso 1 1 calc R U . . .
C2 C 0.3046(5) 0.6529(7) 0.54195(15) 0.0232(7) Uani 1 1 d . . . . .
H2 H 0.3212 0.7562 0.5027 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4783(4) 0.7151(7) 0.59330(12) 0.0223(6) Uani 1 1 d . . . . .
H3A H 0.5140 0.9141 0.5942 0.027 Uiso 1 1 calc R U . . .
H3B H 0.6019 0.6053 0.5878 0.027 Uiso 1 1 calc R U . . .
C4 C 0.3871(4) 0.6284(6) 0.65342(11) 0.0169(6) Uani 1 1 d . . . . .
H4 H 0.4041 0.4249 0.6606 0.020 Uiso 1 1 calc R U . . .
C5 C 0.4772(4) 0.7902(6) 0.71218(12) 0.0180(6) Uani 1 1 d . . . . .
C6 C 0.7527(5) 0.8136(7) 0.79996(14) 0.0299(7) Uani 1 1 d . . . . .
H6A H 0.6548 0.8844 0.8276 0.036 Uiso 1 1 calc R U . . .
H6B H 0.8298 0.9728 0.7858 0.036 Uiso 1 1 calc R U . . .
C7 C 0.9008(5) 0.6118(6) 0.83600(12) 0.0238(7) Uani 1 1 d . . . . .
C8 C 1.0869(5) 0.5439(7) 0.81411(14) 0.0336(9) Uani 1 1 d . . . . .
H8 H 1.1211 0.6285 0.7770 0.040 Uiso 1 1 calc R U . . .
C9 C 1.2226(5) 0.3552(7) 0.84556(14) 0.0292(7) Uani 1 1 d . . . . .
H9 H 1.3469 0.3089 0.8297 0.035 Uiso 1 1 calc R U . . .
C10 C 1.1738(5) 0.2359(7) 0.90040(13) 0.0242(6) Uani 1 1 d . . . . .
C11 C 0.9905(5) 0.2972(7) 0.92366(14) 0.0285(7) Uani 1 1 d . . . . .
H11 H 0.9590 0.2146 0.9613 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8537(4) 0.4812(9) 0.89099(11) 0.0289(6) Uani 1 1 d . . . . .
H12 H 0.7266 0.5193 0.9060 0.035 Uiso 1 1 calc R U . . .
H2B H 0.129(5) 0.853(7) 0.6572(14) 0.019(8) Uiso 1 1 d . . . . .
H2A H 0.068(6) 0.545(11) 0.6523(18) 0.073(14) Uiso 1 1 d . . . . .


_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
Br1 C10 1.900(3) . ?
F1 C2 1.412(3) . ?
O1 C5 1.231(4) . ?
N1 C5 1.320(4) . ?
N1 C6 1.461(4) . ?
N1 H1 0.8700 . ?
N2 C4 1.501(3) . ?
N2 C1 1.503(3) . ?
N2 H2B 0.86(3) . ?
N2 H2A 1.02(5) . ?
C1 C2 1.507(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 C3 1.505(4) . ?
C2 H2 0.9900 . ?
C3 C4 1.534(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 C5 1.529(4) . ?
C4 H4 0.9900 . ?
C6 C7 1.507(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 C8 1.388(4) . ?
C7 C12 1.396(4) . ?
C8 C9 1.379(4) . ?
C8 H8 0.9400 . ?
C9 C10 1.373(4) . ?
C9 H9 0.9400 . ?
C10 C11 1.378(4) . ?
C11 C12 1.379(5) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?

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
C5 N1 C6 121.9(2) . . ?
C5 N1 H1 119.1 . . ?
C6 N1 H1 119.1 . . ?
C4 N2 C1 108.8(2) . . ?
C4 N2 H2B 113(2) . . ?
C1 N2 H2B 108(2) . . ?
C4 N2 H2A 112(3) . . ?
C1 N2 H2A 108(2) . . ?
H2B N2 H2A 108(3) . . ?
N2 C1 C2 104.7(2) . . ?
N2 C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
N2 C1 H1B 110.8 . . ?
C2 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
F1 C2 C3 108.8(3) . . ?
F1 C2 C1 108.4(3) . . ?
C3 C2 C1 104.7(2) . . ?
F1 C2 H2 111.5 . . ?
C3 C2 H2 111.5 . . ?
C1 C2 H2 111.5 . . ?
C2 C3 C4 102.9(2) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
N2 C4 C5 108.5(2) . . ?
N2 C4 C3 103.5(2) . . ?
C5 C4 C3 113.6(2) . . ?
N2 C4 H4 110.3 . . ?
C5 C4 H4 110.3 . . ?
C3 C4 H4 110.3 . . ?
O1 C5 N1 124.8(3) . . ?
O1 C5 C4 119.8(3) . . ?
N1 C5 C4 115.4(2) . . ?
N1 C6 C7 110.0(2) . . ?
N1 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C12 117.9(3) . . ?
C8 C7 C6 120.5(3) . . ?
C12 C7 C6 121.6(3) . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C10 C9 C8 119.1(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 121.2(3) . . ?
C9 C10 Br1 119.7(2) . . ?
C11 C10 Br1 119.1(2) . . ?
C10 C11 C12 119.2(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C7 121.1(3) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?

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
C4 N2 C1 C2 7.2(3) . . . . ?
N2 C1 C2 F1 86.9(3) . . . . ?
N2 C1 C2 C3 -29.1(3) . . . . ?
F1 C2 C3 C4 -76.2(3) . . . . ?
C1 C2 C3 C4 39.6(3) . . . . ?
C1 N2 C4 C5 137.8(3) . . . . ?
C1 N2 C4 C3 16.8(3) . . . . ?
C2 C3 C4 N2 -34.3(3) . . . . ?
C2 C3 C4 C5 -151.8(3) . . . . ?
C6 N1 C5 O1 -2.9(4) . . . . ?
C6 N1 C5 C4 175.2(3) . . . . ?
N2 C4 C5 O1 -28.1(3) . . . . ?
C3 C4 C5 O1 86.5(3) . . . . ?
N2 C4 C5 N1 153.7(2) . . . . ?
C3 C4 C5 N1 -91.7(3) . . . . ?
C5 N1 C6 C7 168.6(2) . . . . ?
N1 C6 C7 C8 77.6(4) . . . . ?
N1 C6 C7 C12 -100.4(3) . . . . ?
C12 C7 C8 C9 -0.4(5) . . . . ?
C6 C7 C8 C9 -178.6(3) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
C8 C9 C10 C11 1.3(5) . . . . ?
C8 C9 C10 Br1 -177.9(2) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
Br1 C10 C11 C12 179.4(3) . . . . ?
C10 C11 C12 C7 -1.9(5) . . . . ?
C8 C7 C12 C11 2.0(5) . . . . ?
C6 C7 C12 C11 -179.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A Cl1 1.02(5) 2.03(5) 3.034(3) 164(3) 1_455
N2 H2B O1 0.86(3) 2.28(3) 2.708(3) 111(2) .
N2 H2B Cl1 0.86(3) 2.42(3) 3.153(3) 143(3) 1_465
C4 H4 O1 0.99 2.39 3.298(4) 152.3 1_545
C3 H3B Cl1 0.98 2.80 3.605(3) 140.1 .
C3 H3A Cl1 0.98 2.89 3.618(3) 132.3 1_565
C1 H1A F1 0.98 2.59 3.338(4) 133.6 1_565
C1 H1A Cl1 0.98 2.89 3.401(3) 113.7 1_465
N1 H1 Cl1 0.87 2.65 3.410(2) 146.6 .

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_dd20119
_database_code_depnum_ccdc_archive 'CCDC 2089259'
loop_
_audit_author_name
_audit_author_address
'Zhuo-Ya Mao'
;fudan university
China
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N2 O2'
_chemical_formula_weight         370.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   9.8421(19)
_cell_length_b                   19.150(4)
_cell_length_c                   10.450(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1969.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    192(2)
_cell_measurement_reflns_used    2003
_cell_measurement_theta_min      4.440
_cell_measurement_theta_max      43.965

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6421
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      192(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            8842
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.220
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3627
_reflns_number_gt                2523
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.982

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0399P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 885 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.4(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3627
_refine_ls_number_parameters     258
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1203
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
O1 O -0.0253(3) 0.41770(16) 0.0802(3) 0.0509(9) Uani 1 1 d . . . . .
O2 O 0.3280(4) 0.56586(17) 0.2262(3) 0.0625(10) Uani 1 1 d . . . . .
N1 N 0.1185(4) 0.46524(18) 0.2267(4) 0.0462(10) Uani 1 1 d . . . . .
N2 N 0.2810(4) 0.59232(18) 0.4349(3) 0.0341(9) Uani 1 1 d . . . . .
C1 C 0.0070(5) 0.4649(2) 0.1536(4) 0.0394(11) Uani 1 1 d . . . . .
C2 C -0.0670(5) 0.5317(2) 0.1740(5) 0.0528(13) Uani 1 1 d . . . . .
H2A H -0.0730 0.5582 0.0929 0.063 Uiso 1 1 calc R U . . .
H2B H -0.1603 0.5225 0.2052 0.063 Uiso 1 1 calc R U . . .
C3 C 0.0096(7) 0.5715(3) 0.2694(6) 0.083(2) Uani 1 1 d . . . . .
H3A H -0.0505 0.5863 0.3403 0.100 Uiso 1 1 calc R U . . .
H3B H 0.0503 0.6136 0.2300 0.100 Uiso 1 1 calc R U . . .
C4 C 0.1219(5) 0.5221(2) 0.3193(5) 0.0463(12) Uani 1 1 d . . . . .
H4 H 0.0992 0.5046 0.4069 0.056 Uiso 1 1 calc R U . . .
C5 C 0.2553(5) 0.5610(2) 0.3201(4) 0.0419(11) Uani 1 1 d . . . . .
C6 C 0.3833(4) 0.6424(2) 0.4603(4) 0.0359(10) Uani 1 1 d . . . . .
C7 C 0.4380(5) 0.6836(2) 0.3639(5) 0.0504(13) Uani 1 1 d . . . . .
H7 H 0.4103 0.6766 0.2778 0.060 Uiso 1 1 calc R U . . .
C8 C 0.5319(6) 0.7344(2) 0.3921(6) 0.0642(16) Uani 1 1 d . . . . .
H8 H 0.5699 0.7616 0.3250 0.077 Uiso 1 1 calc R U . . .
C9 C 0.5717(6) 0.7463(3) 0.5170(7) 0.0695(17) Uani 1 1 d . . . . .
H9 H 0.6359 0.7818 0.5365 0.083 Uiso 1 1 calc R U . . .
C10 C 0.5167(5) 0.7058(2) 0.6128(5) 0.0525(14) Uani 1 1 d . . . . .
H10 H 0.5426 0.7143 0.6989 0.063 Uiso 1 1 calc R U . . .
C11 C 0.4239(4) 0.6527(2) 0.5867(4) 0.0375(11) Uani 1 1 d . . . . .
C12 C 0.3763(4) 0.6098(2) 0.6974(4) 0.0386(11) Uani 1 1 d . . . . .
C13 C 0.3107(5) 0.6414(3) 0.8003(4) 0.0517(13) Uani 1 1 d . . . . .
H13 H 0.2851 0.6891 0.7952 0.062 Uiso 1 1 calc R U . . .
C14 C 0.2829(6) 0.6037(4) 0.9097(5) 0.0661(16) Uani 1 1 d . . . . .
H14 H 0.2402 0.6260 0.9803 0.079 Uiso 1 1 calc R U . . .
C15 C 0.3163(6) 0.5344(3) 0.9171(5) 0.0648(16) Uani 1 1 d . . . . .
H15 H 0.2954 0.5086 0.9922 0.078 Uiso 1 1 calc R U . . .
C16 C 0.3800(5) 0.5022(3) 0.8163(5) 0.0557(14) Uani 1 1 d . . . . .
H16 H 0.4041 0.4543 0.8221 0.067 Uiso 1 1 calc R U . . .
C17 C 0.4094(5) 0.5395(2) 0.7058(4) 0.0436(12) Uani 1 1 d . . . . .
H17 H 0.4523 0.5169 0.6357 0.052 Uiso 1 1 calc R U . . .
C18 C 0.2152(5) 0.4072(2) 0.2316(4) 0.0495(13) Uani 1 1 d . . . . .
H18A H 0.3075 0.4251 0.2130 0.059 Uiso 1 1 calc R U . . .
H18B H 0.1916 0.3728 0.1644 0.059 Uiso 1 1 calc R U . . .
C19 C 0.2165(5) 0.3712(2) 0.3592(5) 0.0452(12) Uani 1 1 d . . . . .
C20 C 0.3263(5) 0.3784(3) 0.4409(5) 0.0494(12) Uani 1 1 d . . . . .
H20 H 0.4015 0.4060 0.4148 0.059 Uiso 1 1 calc R U . . .
C21 C 0.3295(7) 0.3465(3) 0.5591(5) 0.0682(17) Uani 1 1 d . . . . .
H21 H 0.4059 0.3525 0.6135 0.082 Uiso 1 1 calc R U . . .
C22 C 0.2237(9) 0.3067(3) 0.5975(7) 0.082(2) Uani 1 1 d . . . . .
H22 H 0.2254 0.2852 0.6793 0.098 Uiso 1 1 calc R U . . .
C23 C 0.1134(8) 0.2973(3) 0.5180(8) 0.085(2) Uani 1 1 d . . . . .
H23 H 0.0411 0.2676 0.5439 0.102 Uiso 1 1 calc R U . . .
C24 C 0.1075(6) 0.3309(3) 0.4000(6) 0.0672(17) Uani 1 1 d . . . . .
H24 H 0.0290 0.3264 0.3477 0.081 Uiso 1 1 calc R U . . .
H2 H 0.220(5) 0.580(2) 0.498(4) 0.049(14) Uiso 1 1 d . . . . .


_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 C1 1.227(5) . ?
O2 C5 1.218(5) . ?
N1 C1 1.337(5) . ?
N1 C4 1.457(5) . ?
N1 C18 1.464(5) . ?
N2 C5 1.366(5) . ?
N2 C6 1.415(5) . ?
N2 H2 0.92(5) . ?
C1 C2 1.487(6) . ?
C2 C3 1.464(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.546(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.509(7) . ?
C4 H4 1.0000 . ?
C6 C7 1.389(6) . ?
C6 C11 1.394(6) . ?
C7 C8 1.374(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.494(6) . ?
C12 C17 1.388(6) . ?
C12 C13 1.393(6) . ?
C13 C14 1.379(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.370(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.501(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.384(6) . ?
C19 C24 1.388(7) . ?
C20 C21 1.378(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.350(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.393(8) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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
C1 N1 C4 113.7(4) . . ?
C1 N1 C18 123.4(4) . . ?
C4 N1 C18 121.9(3) . . ?
C5 N2 C6 126.5(4) . . ?
C5 N2 H2 113(3) . . ?
C6 N2 H2 121(3) . . ?
O1 C1 N1 124.9(4) . . ?
O1 C1 C2 126.6(4) . . ?
N1 C1 C2 108.4(4) . . ?
C3 C2 C1 107.0(4) . . ?
C3 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
C3 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
C2 C3 C4 106.2(4) . . ?
C2 C3 H3A 110.5 . . ?
C4 C3 H3A 110.5 . . ?
C2 C3 H3B 110.5 . . ?
C4 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
N1 C4 C5 113.1(4) . . ?
N1 C4 C3 102.5(4) . . ?
C5 C4 C3 108.7(4) . . ?
N1 C4 H4 110.7 . . ?
C5 C4 H4 110.7 . . ?
C3 C4 H4 110.7 . . ?
O2 C5 N2 124.4(5) . . ?
O2 C5 C4 123.0(4) . . ?
N2 C5 C4 112.5(4) . . ?
C7 C6 C11 119.7(4) . . ?
C7 C6 N2 121.7(4) . . ?
C11 C6 N2 118.6(4) . . ?
C8 C7 C6 120.5(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.6(5) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 118.8(5) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 121.8(5) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C6 118.5(4) . . ?
C10 C11 C12 117.1(4) . . ?
C6 C11 C12 124.4(4) . . ?
C17 C12 C13 118.8(4) . . ?
C17 C12 C11 120.6(4) . . ?
C13 C12 C11 120.3(4) . . ?
C14 C13 C12 120.3(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.4(5) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.1(5) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 120.1(5) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.2(5) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
N1 C18 C19 112.7(4) . . ?
N1 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C24 118.0(5) . . ?
C20 C19 C18 120.6(4) . . ?
C24 C19 C18 121.4(5) . . ?
C21 C20 C19 121.7(5) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C22 C21 C20 119.9(6) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.1(7) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 120.4(6) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C19 C24 C23 119.8(6) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?

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
C4 N1 C1 O1 -170.9(4) . . . . ?
C18 N1 C1 O1 -2.3(7) . . . . ?
C4 N1 C1 C2 10.8(5) . . . . ?
C18 N1 C1 C2 179.4(4) . . . . ?
O1 C1 C2 C3 -179.7(5) . . . . ?
N1 C1 C2 C3 -1.4(6) . . . . ?
C1 C2 C3 C4 -7.5(6) . . . . ?
C1 N1 C4 C5 -131.9(4) . . . . ?
C18 N1 C4 C5 59.3(6) . . . . ?
C1 N1 C4 C3 -14.9(5) . . . . ?
C18 N1 C4 C3 176.3(5) . . . . ?
C2 C3 C4 N1 12.9(6) . . . . ?
C2 C3 C4 C5 132.9(5) . . . . ?
C6 N2 C5 O2 9.1(7) . . . . ?
C6 N2 C5 C4 -167.9(4) . . . . ?
N1 C4 C5 O2 28.5(6) . . . . ?
C3 C4 C5 O2 -84.7(6) . . . . ?
N1 C4 C5 N2 -154.4(4) . . . . ?
C3 C4 C5 N2 92.4(5) . . . . ?
C5 N2 C6 C7 23.5(6) . . . . ?
C5 N2 C6 C11 -160.0(4) . . . . ?
C11 C6 C7 C8 0.0(7) . . . . ?
N2 C6 C7 C8 176.5(4) . . . . ?
C6 C7 C8 C9 -1.2(8) . . . . ?
C7 C8 C9 C10 0.7(9) . . . . ?
C8 C9 C10 C11 1.0(8) . . . . ?
C9 C10 C11 C6 -2.2(7) . . . . ?
C9 C10 C11 C12 177.0(4) . . . . ?
C7 C6 C11 C10 1.6(6) . . . . ?
N2 C6 C11 C10 -174.9(4) . . . . ?
C7 C6 C11 C12 -177.5(4) . . . . ?
N2 C6 C11 C12 5.9(6) . . . . ?
C10 C11 C12 C17 -113.9(5) . . . . ?
C6 C11 C12 C17 65.3(6) . . . . ?
C10 C11 C12 C13 59.1(6) . . . . ?
C6 C11 C12 C13 -121.8(5) . . . . ?
C17 C12 C13 C14 1.7(7) . . . . ?
C11 C12 C13 C14 -171.3(5) . . . . ?
C12 C13 C14 C15 -1.6(8) . . . . ?
C13 C14 C15 C16 1.1(8) . . . . ?
C14 C15 C16 C17 -0.7(8) . . . . ?
C15 C16 C17 C12 0.9(7) . . . . ?
C13 C12 C17 C16 -1.4(6) . . . . ?
C11 C12 C17 C16 171.7(4) . . . . ?
C1 N1 C18 C19 -112.9(5) . . . . ?
C4 N1 C18 C19 54.8(6) . . . . ?
N1 C18 C19 C20 -108.9(5) . . . . ?
N1 C18 C19 C24 69.8(5) . . . . ?
C24 C19 C20 C21 0.5(7) . . . . ?
C18 C19 C20 C21 179.3(4) . . . . ?
C19 C20 C21 C22 0.3(8) . . . . ?
C20 C21 C22 C23 0.8(9) . . . . ?
C21 C22 C23 C24 -2.7(9) . . . . ?
C20 C19 C24 C23 -2.4(7) . . . . ?
C18 C19 C24 C23 178.8(4) . . . . ?
C22 C23 C24 C19 3.5(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.92(5) 2.11(5) 2.945(5) 151(4) 2_565
C7 H7 O2 0.95 2.33 2.885(6) 116.5 .
C4 H4 O1 1.00 2.45 3.110(6) 122.7 2_565
C3 H3A O1 0.99 2.62 3.259(7) 122.6 2_565
C3 H3A O1 0.99 2.62 3.259(7) 122.6 2_565
C4 H4 O1 1.00 2.45 3.110(6) 122.7 2_565
C7 H7 O2 0.95 2.33 2.885(6) 116.5 .
N2 H2 O1 0.92(5) 2.11(5) 2.945(5) 151(4) 2_565

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_ddz20133
_database_code_depnum_ccdc_archive 'CCDC 2089258'
loop_
_audit_author_name
_audit_author_address
'Zhuo-Ya Mao'
;fudan university
China
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H30 N2 O4'
_chemical_formula_weight         362.46

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.4680(13)
_cell_length_b                   14.2172(13)
_cell_length_c                   10.9007(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.363(3)
_cell_angle_gamma                90
_cell_volume                     2085.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5732
_cell_measurement_theta_min      5.519
_cell_measurement_theta_max      54.014

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6955
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            29338
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.758
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3881
_reflns_number_gt                2544
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0434P)²+0.4768P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0173(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3881
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1293
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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
O1 O 1.00764(12) 0.27939(11) 0.29122(18) 0.0783(5) Uani 1 1 d . . . . .
H1 H 0.9768 0.2303 0.2795 0.118 Uiso 1 1 calc R U . . .
O2 O 0.88676(13) 0.12250(10) 0.29671(14) 0.0731(5) Uani 1 1 d . . . . .
O3 O 0.68306(11) 0.34564(11) 0.16070(13) 0.0616(4) Uani 1 1 d . . . . .
O4 O 0.64388(10) 0.23010(10) 0.29508(12) 0.0569(4) Uani 1 1 d . . . . .
N1 N 0.78910(12) 0.30192(11) 0.31774(14) 0.0486(4) Uani 1 1 d . . . . .
N2 N 0.78492(12) 0.07454(11) 0.44455(15) 0.0506(5) Uani 1 1 d . . . . .
H2 H 0.7498 0.0943 0.5034 0.061 Uiso 1 1 calc R U . . .
C1 C 0.86056(15) 0.37818(14) 0.30074(19) 0.0499(5) Uani 1 1 d . . . . .
H1A H 0.8729 0.3849 0.2132 0.060 Uiso 1 1 calc R U . . .
C2 C 0.95365(16) 0.33904(15) 0.3679(2) 0.0590(6) Uani 1 1 d . . . . .
H2A H 0.9961 0.3908 0.3981 0.071 Uiso 1 1 calc R U . . .
C3 C 0.91050(16) 0.28704(15) 0.4756(2) 0.0564(6) Uani 1 1 d . . . . .
H3A H 0.8959 0.3304 0.5412 0.068 Uiso 1 1 calc R U . . .
H3B H 0.9566 0.2398 0.5076 0.068 Uiso 1 1 calc R U . . .
C4 C 0.81500(15) 0.24115(13) 0.42308(17) 0.0465(5) Uani 1 1 d . . . . .
H4 H 0.7629 0.2436 0.4832 0.056 Uiso 1 1 calc R U . . .
C5 C 0.83171(16) 0.13982(14) 0.38168(19) 0.0502(5) Uani 1 1 d . . . . .
C6 C 0.78641(17) -0.02838(14) 0.4248(2) 0.0551(6) Uani 1 1 d . . . . .
C7 C 0.88961(19) -0.06704(17) 0.4546(3) 0.0819(8) Uani 1 1 d . . . . .
H7A H 0.9359 -0.0396 0.4002 0.123 Uiso 1 1 calc R U . . .
H7B H 0.8891 -0.1341 0.4443 0.123 Uiso 1 1 calc R U . . .
H7C H 0.9091 -0.0519 0.5379 0.123 Uiso 1 1 calc R U . . .
C8 C 0.7120(2) -0.06840(17) 0.5117(3) 0.0811(8) Uani 1 1 d . . . . .
H8A H 0.7328 -0.0539 0.5948 0.122 Uiso 1 1 calc R U . . .
H8B H 0.7082 -0.1354 0.5016 0.122 Uiso 1 1 calc R U . . .
H8C H 0.6478 -0.0412 0.4936 0.122 Uiso 1 1 calc R U . . .
C9 C 0.7555(2) -0.05117(18) 0.2931(2) 0.0822(8) Uani 1 1 d . . . . .
H9A H 0.6898 -0.0275 0.2752 0.123 Uiso 1 1 calc R U . . .
H9B H 0.7560 -0.1181 0.2816 0.123 Uiso 1 1 calc R U . . .
H9C H 0.8011 -0.0224 0.2390 0.123 Uiso 1 1 calc R U . . .
C10 C 0.82625(16) 0.47128(14) 0.35106(18) 0.0492(5) Uani 1 1 d . . . . .
C11 C 0.87841(18) 0.55239(16) 0.3270(2) 0.0654(6) Uani 1 1 d . . . . .
H11 H 0.9342 0.5490 0.2796 0.078 Uiso 1 1 calc R U . . .
C12 C 0.8494(2) 0.63804(17) 0.3718(3) 0.0821(8) Uani 1 1 d . . . . .
H12 H 0.8849 0.6921 0.3539 0.099 Uiso 1 1 calc R U . . .
C13 C 0.7686(2) 0.64357(18) 0.4425(3) 0.0838(8) Uani 1 1 d . . . . .
H13 H 0.7495 0.7015 0.4735 0.101 Uiso 1 1 calc R U . . .
C14 C 0.7152(2) 0.56439(18) 0.4682(2) 0.0771(8) Uani 1 1 d . . . . .
H14 H 0.6601 0.5683 0.5167 0.092 Uiso 1 1 calc R U . . .
C15 C 0.74380(18) 0.47914(16) 0.4216(2) 0.0637(6) Uani 1 1 d . . . . .
H15 H 0.7069 0.4256 0.4380 0.076 Uiso 1 1 calc R U . . .
C16 C 0.70352(16) 0.29661(15) 0.24986(19) 0.0497(5) Uani 1 1 d . . . . .
C17 C 0.54631(16) 0.20836(18) 0.2358(2) 0.0639(6) Uani 1 1 d . . . . .
C18 C 0.5614(2) 0.1694(2) 0.1091(2) 0.0962(10) Uani 1 1 d . . . . .
H18A H 0.5877 0.2178 0.0582 0.144 Uiso 1 1 calc R U . . .
H18B H 0.4990 0.1480 0.0739 0.144 Uiso 1 1 calc R U . . .
H18C H 0.6073 0.1178 0.1147 0.144 Uiso 1 1 calc R U . . .
C19 C 0.5073(2) 0.1328(2) 0.3186(3) 0.0903(9) Uani 1 1 d . . . . .
H19A H 0.5530 0.0809 0.3224 0.136 Uiso 1 1 calc R U . . .
H19B H 0.4438 0.1114 0.2864 0.136 Uiso 1 1 calc R U . . .
H19C H 0.5003 0.1579 0.3995 0.136 Uiso 1 1 calc R U . . .
C20 C 0.4806(2) 0.2939(2) 0.2356(3) 0.1054(11) Uani 1 1 d . . . . .
H20A H 0.4788 0.3188 0.3174 0.158 Uiso 1 1 calc R U . . .
H20B H 0.4146 0.2769 0.2072 0.158 Uiso 1 1 calc R U . . .
H20C H 0.5065 0.3407 0.1821 0.158 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
O1 C2 1.413(2) . ?
O1 H1 0.8200 . ?
O2 C5 1.235(2) . ?
O3 C16 1.218(2) . ?
O4 C16 1.347(2) . ?
O4 C17 1.473(3) . ?
N1 C16 1.346(3) . ?
N1 C1 1.467(2) . ?
N1 C4 1.468(2) . ?
N2 C5 1.328(2) . ?
N2 C6 1.479(3) . ?
N2 H2 0.8600 . ?
C1 C10 1.512(3) . ?
C1 C2 1.530(3) . ?
C1 H1A 0.9800 . ?
C2 C3 1.523(3) . ?
C2 H2A 0.9800 . ?
C3 C4 1.532(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.529(3) . ?
C4 H4 0.9800 . ?
C6 C9 1.514(3) . ?
C6 C8 1.518(3) . ?
C6 C7 1.517(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.381(3) . ?
C10 C15 1.381(3) . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.361(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C17 C20 1.504(4) . ?
C17 C18 1.509(3) . ?
C17 C19 1.511(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C2 O1 H1 109.5 . . ?
C16 O4 C17 121.43(16) . . ?
C16 N1 C1 121.57(17) . . ?
C16 N1 C4 124.59(17) . . ?
C1 N1 C4 113.46(16) . . ?
C5 N2 C6 127.36(17) . . ?
C5 N2 H2 116.3 . . ?
C6 N2 H2 116.3 . . ?
N1 C1 C10 112.92(16) . . ?
N1 C1 C2 101.51(16) . . ?
C10 C1 C2 113.65(17) . . ?
N1 C1 H1A 109.5 . . ?
C10 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
O1 C2 C3 112.76(18) . . ?
O1 C2 C1 111.49(19) . . ?
C3 C2 C1 102.38(17) . . ?
O1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
C2 C3 C4 105.04(17) . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C4 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
N1 C4 C5 110.90(15) . . ?
N1 C4 C3 102.16(15) . . ?
C5 C4 C3 112.34(17) . . ?
N1 C4 H4 110.4 . . ?
C5 C4 H4 110.4 . . ?
C3 C4 H4 110.4 . . ?
O2 C5 N2 124.06(19) . . ?
O2 C5 C4 120.63(18) . . ?
N2 C5 C4 115.30(17) . . ?
N2 C6 C9 110.16(18) . . ?
N2 C6 C8 105.48(17) . . ?
C9 C6 C8 110.4(2) . . ?
N2 C6 C7 110.19(18) . . ?
C9 C6 C7 109.8(2) . . ?
C8 C6 C7 110.7(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 117.7(2) . . ?
C11 C10 C1 119.76(19) . . ?
C15 C10 C1 122.51(18) . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 119.3(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C10 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
O3 C16 N1 124.5(2) . . ?
O3 C16 O4 125.1(2) . . ?
N1 C16 O4 110.38(17) . . ?
O4 C17 C20 110.2(2) . . ?
O4 C17 C18 109.05(18) . . ?
C20 C17 C18 113.4(2) . . ?
O4 C17 C19 102.31(18) . . ?
C20 C17 C19 110.9(2) . . ?
C18 C17 C19 110.4(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C16 N1 C1 C10 73.5(2) . . . . ?
C4 N1 C1 C10 -99.72(19) . . . . ?
C16 N1 C1 C2 -164.46(18) . . . . ?
C4 N1 C1 C2 22.3(2) . . . . ?
N1 C1 C2 O1 84.60(19) . . . . ?
C10 C1 C2 O1 -153.86(17) . . . . ?
N1 C1 C2 C3 -36.20(19) . . . . ?
C10 C1 C2 C3 85.3(2) . . . . ?
O1 C2 C3 C4 -81.4(2) . . . . ?
C1 C2 C3 C4 38.5(2) . . . . ?
C16 N1 C4 C5 68.3(2) . . . . ?
C1 N1 C4 C5 -118.73(18) . . . . ?
C16 N1 C4 C3 -171.81(18) . . . . ?
C1 N1 C4 C3 1.2(2) . . . . ?
C2 C3 C4 N1 -24.7(2) . . . . ?
C2 C3 C4 C5 94.21(19) . . . . ?
C6 N2 C5 O2 -1.8(3) . . . . ?
C6 N2 C5 C4 179.44(18) . . . . ?
N1 C4 C5 O2 49.6(3) . . . . ?
C3 C4 C5 O2 -64.0(3) . . . . ?
N1 C4 C5 N2 -131.55(19) . . . . ?
C3 C4 C5 N2 114.8(2) . . . . ?
C5 N2 C6 C9 -54.7(3) . . . . ?
C5 N2 C6 C8 -173.8(2) . . . . ?
C5 N2 C6 C7 66.6(3) . . . . ?
N1 C1 C10 C11 -170.94(19) . . . . ?
C2 C1 C10 C11 74.1(2) . . . . ?
N1 C1 C10 C15 9.3(3) . . . . ?
C2 C1 C10 C15 -105.7(2) . . . . ?
C15 C10 C11 C12 0.1(3) . . . . ?
C1 C10 C11 C12 -179.7(2) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C10 1.1(4) . . . . ?
C11 C10 C15 C14 -1.0(3) . . . . ?
C1 C10 C15 C14 178.8(2) . . . . ?
C1 N1 C16 O3 9.3(3) . . . . ?
C4 N1 C16 O3 -178.22(18) . . . . ?
C1 N1 C16 O4 -170.23(16) . . . . ?
C4 N1 C16 O4 2.2(3) . . . . ?
C17 O4 C16 O3 1.9(3) . . . . ?
C17 O4 C16 N1 -178.51(17) . . . . ?
C16 O4 C17 C20 -61.0(3) . . . . ?
C16 O4 C17 C18 64.1(3) . . . . ?
C16 O4 C17 C19 -178.99(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C20 H20C O3 0.96 2.40 2.970(3) 117.7 .
C18 H18A O3 0.96 2.47 3.033(3) 117.6 .
C9 H9C O2 0.96 2.43 3.036(3) 120.7 .
C7 H7A O2 0.96 2.64 3.197(3) 117.5 .
C4 H4 O3 0.98 2.58 3.431(2) 144.5 4_566
N2 H2 O3 0.86 2.15 2.998(2) 171.0 4_566
O1 H1 O2 0.82 1.97 2.763(2) 163.5 .

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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 
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data_mo_ddz20072_0m
_database_code_depnum_ccdc_archive 'CCDC 2089257'
loop_
_audit_author_name
_audit_author_address
'Zhuo-Ya Mao'
;fudan university
China
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 N2 O2'
_chemical_formula_weight         354.48

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'
'-x, -y, -z'

_cell_length_a                   9.9031(14)
_cell_length_b                   9.9209(15)
_cell_length_c                   10.8025(14)
_cell_angle_alpha                72.827(4)
_cell_angle_beta                 89.188(4)
_cell_angle_gamma                78.782(5)
_cell_volume                     993.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7140
_cell_measurement_theta_min      4.386
_cell_measurement_theta_max      53.188

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2216
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            22231
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.717
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3683
_reflns_number_gt                2676
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0904P)²+0.0993P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.075(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3683
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1651
_refine_ls_wR_factor_gt          0.1469
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O1 O 0.38188(14) 0.62796(16) 0.48805(11) 0.0571(4) Uani 1 1 d . . . . .
O2 O 0.62672(14) 0.58100(15) 0.02319(12) 0.0578(4) Uani 1 1 d . . . . .
N1 N 0.40181(14) 0.58665(16) 0.29037(13) 0.0414(4) Uani 1 1 d . . . . .
N2 N 0.65089(15) 0.44078(16) 0.23247(14) 0.0456(4) Uani 1 1 d . . . . .
H2 H 0.6206 0.4320 0.3089 0.055 Uiso 1 1 calc R U . . .
C1 C 0.42657(17) 0.6526(2) 0.37857(16) 0.0429(5) Uani 1 1 d . . . . .
C2 C 0.51885(18) 0.7571(2) 0.31917(17) 0.0453(5) Uani 1 1 d . . . . .
H2A H 0.6144 0.7042 0.3364 0.054 Uiso 1 1 calc R U . . .
C3 C 0.5052(2) 0.8852(3) 0.3719(2) 0.0643(6) Uani 1 1 d . . . . .
H3A H 0.5840 0.9306 0.3477 0.077 Uiso 1 1 calc R U . . .
H3B H 0.5061 0.8513 0.4659 0.077 Uiso 1 1 calc R U . . .
C4 C 0.3736(3) 0.9965(3) 0.3214(2) 0.0731(7) Uani 1 1 d . . . . .
H4A H 0.2946 0.9567 0.3576 0.088 Uiso 1 1 calc R U . . .
H4B H 0.3747 1.0808 0.3492 0.088 Uiso 1 1 calc R U . . .
C5 C 0.3600(3) 1.0402(2) 0.1745(2) 0.0700(7) Uani 1 1 d . . . . .
H5A H 0.4376 1.0824 0.1380 0.084 Uiso 1 1 calc R U . . .
H5B H 0.2763 1.1121 0.1442 0.084 Uiso 1 1 calc R U . . .
C6 C 0.3555(2) 0.9099(2) 0.12955(19) 0.0544(6) Uani 1 1 d . . . . .
H6A H 0.3460 0.9399 0.0356 0.065 Uiso 1 1 calc R U . . .
H6B H 0.2749 0.8715 0.1630 0.065 Uiso 1 1 calc R U . . .
C7 C 0.48419(18) 0.7908(2) 0.17376(17) 0.0434(5) Uani 1 1 d . . . . .
H7 H 0.5627 0.8173 0.1227 0.052 Uiso 1 1 calc R U . . .
C8 C 0.45769(17) 0.64581(19) 0.16481(16) 0.0408(5) Uani 1 1 d . . . . .
H8 H 0.3863 0.6646 0.0966 0.049 Uiso 1 1 calc R U . . .
C9 C 0.58698(18) 0.5508(2) 0.13416(16) 0.0419(5) Uani 1 1 d . . . . .
C10 C 0.76941(19) 0.3347(2) 0.21687(17) 0.0448(5) Uani 1 1 d . . . . .
H10 H 0.8114 0.3770 0.1355 0.054 Uiso 1 1 calc R U . . .
C11 C 0.87738(19) 0.2968(2) 0.32646(19) 0.0512(5) Uani 1 1 d . . . . .
H11A H 0.8371 0.2583 0.4086 0.061 Uiso 1 1 calc R U . . .
H11B H 0.9084 0.3831 0.3286 0.061 Uiso 1 1 calc R U . . .
C12 C 1.0000(2) 0.1861(2) 0.3080(2) 0.0652(6) Uani 1 1 d . . . . .
H12A H 1.0458 0.2285 0.2305 0.078 Uiso 1 1 calc R U . . .
H12B H 1.0654 0.1594 0.3814 0.078 Uiso 1 1 calc R U . . .
C13 C 0.9560(3) 0.0530(3) 0.2961(3) 0.0769(8) Uani 1 1 d . . . . .
H13A H 0.9201 0.0040 0.3775 0.092 Uiso 1 1 calc R U . . .
H13B H 1.0353 -0.0121 0.2786 0.092 Uiso 1 1 calc R U . . .
C14 C 0.8464(3) 0.0906(3) 0.1882(3) 0.0791(8) Uani 1 1 d . . . . .
H14A H 0.8153 0.0042 0.1867 0.095 Uiso 1 1 calc R U . . .
H14B H 0.8856 0.1291 0.1054 0.095 Uiso 1 1 calc R U . . .
C15 C 0.7243(2) 0.2011(2) 0.2072(2) 0.0637(6) Uani 1 1 d . . . . .
H15A H 0.6579 0.2270 0.1347 0.076 Uiso 1 1 calc R U . . .
H15B H 0.6797 0.1591 0.2857 0.076 Uiso 1 1 calc R U . . .
C16 C 0.31461(19) 0.4805(2) 0.31172(19) 0.0499(5) Uani 1 1 d . . . . .
H16A H 0.3197 0.4271 0.4032 0.060 Uiso 1 1 calc R U . . .
H16B H 0.3484 0.4128 0.2639 0.060 Uiso 1 1 calc R U . . .
C17 C 0.16645(18) 0.5498(2) 0.26911(17) 0.0425(5) Uani 1 1 d . . . . .
C18 C 0.0806(2) 0.6110(2) 0.3484(2) 0.0586(6) Uani 1 1 d . . . . .
H18 H 0.1132 0.6053 0.4305 0.070 Uiso 1 1 calc R U . . .
C19 C -0.0530(2) 0.6805(3) 0.3070(3) 0.0722(7) Uani 1 1 d . . . . .
H19 H -0.1102 0.7208 0.3613 0.087 Uiso 1 1 calc R U . . .
C20 C -0.1010(2) 0.6899(3) 0.1864(3) 0.0733(7) Uani 1 1 d . . . . .
H20 H -0.1904 0.7382 0.1579 0.088 Uiso 1 1 calc R U . . .
C21 C -0.0179(2) 0.6284(3) 0.1070(2) 0.0704(7) Uani 1 1 d . . . . .
H21 H -0.0513 0.6338 0.0252 0.085 Uiso 1 1 calc R U . . .
C22 C 0.1155(2) 0.5584(2) 0.14855(19) 0.0562(6) Uani 1 1 d . . . . .
H22 H 0.1715 0.5167 0.0945 0.067 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
O1 C1 1.229(2) . ?
O2 C9 1.226(2) . ?
N1 C1 1.354(2) . ?
N1 C16 1.454(2) . ?
N1 C8 1.458(2) . ?
N2 C9 1.336(2) . ?
N2 C10 1.460(2) . ?
N2 H2 0.8600 . ?
C1 C2 1.511(3) . ?
C2 C3 1.522(3) . ?
C2 C7 1.535(2) . ?
C2 H2A 0.9800 . ?
C3 C4 1.523(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.517(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.517(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.532(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.542(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.530(2) . ?
C8 H8 0.9800 . ?
C10 C15 1.511(3) . ?
C10 C11 1.517(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.525(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.509(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.516(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.522(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.509(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C22 1.376(3) . ?
C17 C18 1.383(3) . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.364(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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
C1 N1 C16 124.11(15) . . ?
C1 N1 C8 112.92(16) . . ?
C16 N1 C8 122.57(15) . . ?
C9 N2 C10 123.41(14) . . ?
C9 N2 H2 118.3 . . ?
C10 N2 H2 118.3 . . ?
O1 C1 N1 124.76(19) . . ?
O1 C1 C2 127.14(17) . . ?
N1 C1 C2 108.09(15) . . ?
C1 C2 C3 114.98(16) . . ?
C1 C2 C7 101.67(14) . . ?
C3 C2 C7 116.71(17) . . ?
C1 C2 H2A 107.7 . . ?
C3 C2 H2A 107.7 . . ?
C7 C2 H2A 107.7 . . ?
C2 C3 C4 112.51(17) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 110.92(18) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 110.09(19) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
C5 C6 C7 112.95(17) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 C2 111.36(14) . . ?
C6 C7 C8 111.09(15) . . ?
C2 C7 C8 102.29(14) . . ?
C6 C7 H7 110.6 . . ?
C2 C7 H7 110.6 . . ?
C8 C7 H7 110.6 . . ?
N1 C8 C9 114.99(14) . . ?
N1 C8 C7 102.32(13) . . ?
C9 C8 C7 112.66(15) . . ?
N1 C8 H8 108.9 . . ?
C9 C8 H8 108.9 . . ?
C7 C8 H8 108.9 . . ?
O2 C9 N2 124.26(16) . . ?
O2 C9 C8 118.76(15) . . ?
N2 C9 C8 116.97(15) . . ?
N2 C10 C15 110.58(16) . . ?
N2 C10 C11 111.56(14) . . ?
C15 C10 C11 110.63(16) . . ?
N2 C10 H10 108.0 . . ?
C15 C10 H10 108.0 . . ?
C11 C10 H10 108.0 . . ?
C10 C11 C12 110.58(16) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 111.63(19) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 111.17(19) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.97(18) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C10 C15 C14 111.19(19) . . ?
C10 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C10 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N1 C16 C17 111.75(15) . . ?
N1 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N1 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C22 C17 C18 118.59(18) . . ?
C22 C17 C16 120.75(16) . . ?
C18 C17 C16 120.61(17) . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.3(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 119.8(2) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C17 C22 C21 120.8(2) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?

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
C16 N1 C1 O1 2.2(3) . . . . ?
C8 N1 C1 O1 174.95(15) . . . . ?
C16 N1 C1 C2 -178.76(14) . . . . ?
C8 N1 C1 C2 -5.96(18) . . . . ?
O1 C1 C2 C3 -27.9(2) . . . . ?
N1 C1 C2 C3 152.99(16) . . . . ?
O1 C1 C2 C7 -155.00(16) . . . . ?
N1 C1 C2 C7 25.94(17) . . . . ?
C1 C2 C3 C4 -74.8(2) . . . . ?
C7 C2 C3 C4 44.2(3) . . . . ?
C2 C3 C4 C5 -52.4(3) . . . . ?
C3 C4 C5 C6 60.1(3) . . . . ?
C4 C5 C6 C7 -59.2(3) . . . . ?
C5 C6 C7 C2 48.9(2) . . . . ?
C5 C6 C7 C8 162.16(17) . . . . ?
C1 C2 C7 C6 84.15(18) . . . . ?
C3 C2 C7 C6 -41.8(2) . . . . ?
C1 C2 C7 C8 -34.57(15) . . . . ?
C3 C2 C7 C8 -160.49(16) . . . . ?
C1 N1 C8 C9 105.85(17) . . . . ?
C16 N1 C8 C9 -81.22(19) . . . . ?
C1 N1 C8 C7 -16.62(17) . . . . ?
C16 N1 C8 C7 156.31(14) . . . . ?
C6 C7 C8 N1 -87.49(16) . . . . ?
C2 C7 C8 N1 31.42(15) . . . . ?
C6 C7 C8 C9 148.47(15) . . . . ?
C2 C7 C8 C9 -92.62(16) . . . . ?
C10 N2 C9 O2 -5.8(3) . . . . ?
C10 N2 C9 C8 175.47(16) . . . . ?
N1 C8 C9 O2 168.02(17) . . . . ?
C7 C8 C9 O2 -75.3(2) . . . . ?
N1 C8 C9 N2 -13.2(2) . . . . ?
C7 C8 C9 N2 103.51(19) . . . . ?
C9 N2 C10 C15 -97.5(2) . . . . ?
C9 N2 C10 C11 138.97(19) . . . . ?
N2 C10 C11 C12 180.00(17) . . . . ?
C15 C10 C11 C12 56.5(2) . . . . ?
C10 C11 C12 C13 -55.9(3) . . . . ?
C11 C12 C13 C14 55.2(3) . . . . ?
C12 C13 C14 C15 -55.0(3) . . . . ?
N2 C10 C15 C14 178.87(17) . . . . ?
C11 C10 C15 C14 -57.0(2) . . . . ?
C13 C14 C15 C10 56.2(3) . . . . ?
C1 N1 C16 C17 89.8(2) . . . . ?
C8 N1 C16 C17 -82.31(19) . . . . ?
N1 C16 C17 C22 96.5(2) . . . . ?
N1 C16 C17 C18 -80.9(2) . . . . ?
C22 C17 C18 C19 -0.6(3) . . . . ?
C16 C17 C18 C19 176.9(2) . . . . ?
C17 C18 C19 C20 -0.4(4) . . . . ?
C18 C19 C20 C21 1.2(4) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C18 C17 C22 C21 0.8(3) . . . . ?
C16 C17 C22 C21 -176.6(2) . . . . ?
C20 C21 C22 C17 -0.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11A O1 0.97 2.64 3.340(2) 129.7 2_666
N2 H2 O1 0.86 2.10 2.9202(19) 159.9 2_666

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-4

