# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11_a
_database_code_depnum_ccdc_archive 'CCDC 1967692'
loop_
_audit_author_name
_audit_author_address
'Changduo Pan'
;Jiangsu university of technelogy
China
;
_audit_update_record             
;
2019-11-23 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H26 N2 O2'
_chemical_formula_weight         314.42

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                   6.0543(9)
_cell_length_b                   8.5333(14)
_cell_length_c                   34.582(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1786.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2433
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.91

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            12288
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.356
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3158
_reflns_number_gt                2217
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1193P)²+0.8279P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.050(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3158
_refine_ls_number_parameters     215
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0779
_refine_ls_wR_factor_ref         0.2301
_refine_ls_wR_factor_gt          0.2075
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.079
_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
C1 C 0.4893(13) 0.1651(8) 0.6760(2) 0.058(2) Uani 1 1 d . U . . .
H1A H 0.478088 0.084727 0.695327 0.087 Uiso 1 1 calc R U . . .
H1B H 0.580509 0.128813 0.655138 0.087 Uiso 1 1 calc R U . . .
H1C H 0.344704 0.189615 0.666347 0.087 Uiso 1 1 calc R U . . .
C2 C 0.8355(12) 0.2842(10) 0.7043(2) 0.060(2) Uani 1 1 d . U . . .
H2A H 0.901962 0.381123 0.712279 0.090 Uiso 1 1 calc R U . . .
H2B H 0.912264 0.244279 0.682087 0.090 Uiso 1 1 calc R U . . .
H2C H 0.844494 0.209562 0.724992 0.090 Uiso 1 1 calc R U . . .
C3 C 0.4706(13) 0.3510(9) 0.7315(2) 0.0577(19) Uani 1 1 d . U . . .
H3A H 0.529657 0.445591 0.742371 0.087 Uiso 1 1 calc R U . . .
H3B H 0.489280 0.266441 0.749502 0.087 Uiso 1 1 calc R U . . .
H3C H 0.316258 0.364991 0.726133 0.087 Uiso 1 1 calc R U . . .
C4 C 0.5926(10) 0.3126(8) 0.69393(19) 0.0426(16) Uani 1 1 d . U . . .
C5 C 0.5703(11) 0.4499(8) 0.6660(2) 0.0509(17) Uani 1 1 d . U . . .
C6 C 0.6666(10) 0.4510(7) 0.62692(18) 0.0384(14) Uani 1 1 d . U . . .
C7 C 0.8004(10) 0.3343(7) 0.61174(19) 0.0397(14) Uani 1 1 d . U . . .
H7 H 0.842799 0.244534 0.625051 0.048 Uiso 1 1 calc R U . . .
C8 C 1.0027(9) 0.2748(7) 0.54923(19) 0.0392(15) Uani 1 1 d . U . . .
H8 H 1.017741 0.330458 0.524584 0.047 Uiso 1 1 calc R U . . .
C9 C 0.8977(13) 0.1166(8) 0.5413(2) 0.058(2) Uani 1 1 d . U . . .
H9A H 0.865899 0.065181 0.565303 0.087 Uiso 1 1 calc R U . . .
H9B H 0.997594 0.053405 0.526381 0.087 Uiso 1 1 calc R U . . .
H9C H 0.763091 0.131262 0.527026 0.087 Uiso 1 1 calc R U . . .
C10 C 1.2301(11) 0.2568(10) 0.5667(3) 0.067(2) Uani 1 1 d . U . . .
H10A H 1.292668 0.358469 0.571258 0.101 Uiso 1 1 calc R U . . .
H10B H 1.322957 0.199518 0.549156 0.101 Uiso 1 1 calc R U . . .
H10C H 1.219232 0.200882 0.590690 0.101 Uiso 1 1 calc R U . . .
C11 C 0.6425(9) 0.5685(7) 0.59694(19) 0.0364(14) Uani 1 1 d . U . . .
C12 C 0.7648(9) 0.5100(7) 0.56476(19) 0.0357(14) Uani 1 1 d . U . . .
C13 C 0.6885(10) 0.7102(7) 0.5255(2) 0.0460(16) Uani 1 1 d . U . . .
H13 H 0.700622 0.761047 0.501817 0.055 Uiso 1 1 calc R U . . .
C14 C 0.5603(10) 0.7799(7) 0.5544(2) 0.0424(15) Uani 1 1 d . U . . .
H14 H 0.489402 0.874245 0.549183 0.051 Uiso 1 1 calc R U . . .
C15 C 0.5361(9) 0.7127(7) 0.59045(19) 0.0368(14) Uani 1 1 d . U . . .
C16 C 0.3957(9) 0.7999(7) 0.61930(19) 0.0402(15) Uani 1 1 d . U . . .
H16A H 0.402678 0.911198 0.613714 0.048 Uiso 1 1 calc R U . . .
H16B H 0.455238 0.783658 0.645024 0.048 Uiso 1 1 calc R U . . .
C17 C 0.1543(9) 0.7472(7) 0.6186(2) 0.0439(16) Uani 1 1 d . U . . .
H17A H 0.095331 0.757805 0.592683 0.053 Uiso 1 1 calc R U . . .
H17B H 0.144442 0.637777 0.626069 0.053 Uiso 1 1 calc R U . . .
C18 C 0.0210(10) 0.8467(7) 0.6464(2) 0.0437(16) Uani 1 1 d . U . . .
C19 C -0.0047(14) 0.7895(10) 0.6863(2) 0.072(2) Uani 1 1 d . U . . .
H19A H -0.039749 0.875809 0.703034 0.108 Uiso 1 1 calc R U . . .
H19B H 0.130699 0.741722 0.694680 0.108 Uiso 1 1 calc R U . . .
H19C H -0.121667 0.713684 0.687258 0.108 Uiso 1 1 calc R U . . .
N1 N 0.8619(8) 0.3686(6) 0.57466(16) 0.0399(13) Uani 1 1 d . U . . .
N2 N 0.7946(8) 0.5742(6) 0.53024(16) 0.0420(13) Uani 1 1 d . U . . .
O1 O 0.4721(15) 0.5655(8) 0.6780(2) 0.129(3) Uani 1 1 d . U . . .
O2 O -0.0472(10) 0.9734(6) 0.63666(18) 0.0739(17) Uani 1 1 d . 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
C1 C4 1.536(10) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C4 1.533(10) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.530(10) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.525(10) . ?
C5 O1 1.224(8) . ?
C5 C6 1.471(9) . ?
C6 C7 1.387(8) . ?
C6 C11 1.450(9) . ?
C7 N1 1.367(8) . ?
C7 H7 0.9300 . ?
C8 N1 1.463(7) . ?
C8 C9 1.517(9) . ?
C8 C10 1.511(9) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C15 1.407(8) . ?
C11 C12 1.427(9) . ?
C12 N2 1.326(8) . ?
C12 N1 1.385(7) . ?
C13 N2 1.336(8) . ?
C13 C14 1.398(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.507(8) . ?
C16 C17 1.529(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.516(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O2 1.205(8) . ?
C18 C19 1.471(10) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C2 110.8(6) . . ?
C5 C4 C1 109.7(6) . . ?
C2 C4 C1 110.8(6) . . ?
C5 C4 C3 109.3(5) . . ?
C2 C4 C3 107.4(6) . . ?
C1 C4 C3 108.7(6) . . ?
O1 C5 C6 119.9(6) . . ?
O1 C5 C4 116.6(6) . . ?
C6 C5 C4 123.5(5) . . ?
C7 C6 C11 106.5(5) . . ?
C7 C6 C5 125.1(6) . . ?
C11 C6 C5 128.4(5) . . ?
N1 C7 C6 111.2(5) . . ?
N1 C7 H7 124.4 . . ?
C6 C7 H7 124.4 . . ?
N1 C8 C9 110.6(5) . . ?
N1 C8 C10 110.3(6) . . ?
C9 C8 C10 111.3(6) . . ?
N1 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C10 C8 H8 108.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C11 C12 114.8(6) . . ?
C15 C11 C6 139.9(6) . . ?
C12 C11 C6 105.3(5) . . ?
N2 C12 N1 121.7(6) . . ?
N2 C12 C11 128.9(5) . . ?
N1 C12 C11 109.4(6) . . ?
N2 C13 C14 123.3(6) . . ?
N2 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
C15 C14 C13 121.9(6) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C11 117.3(6) . . ?
C14 C15 C16 116.9(5) . . ?
C11 C15 C16 125.8(6) . . ?
C15 C16 C17 112.6(5) . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 109.5(5) . . ?
C18 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O2 C18 C19 121.6(7) . . ?
O2 C18 C17 120.5(7) . . ?
C19 C18 C17 117.7(6) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 N1 C12 107.6(5) . . ?
C7 N1 C8 127.3(5) . . ?
C12 N1 C8 125.1(6) . . ?
C12 N2 C13 113.8(5) . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.076

