# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_WYQ20210318
_database_code_depnum_ccdc_archive 'CCDC 2164754'
loop_
_audit_author_name
_audit_author_address
'lei wang'
;Yangzhou university
China
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H22 N2 O'
_chemical_formula_sum            'C17 H22 N2 O'
_chemical_formula_weight         270.36

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.328(3)
_cell_length_b                   19.134(8)
_cell_length_c                   10.288(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.713(13)
_cell_angle_gamma                90
_cell_volume                     1592.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4222
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      24.57

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_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            14839
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.733
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3122
_reflns_number_gt                1838
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0708P)²+0.1661P] 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         3122
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1516
_refine_ls_wR_factor_gt          0.1276
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.6168(3) -0.02076(10) 0.8759(2) 0.0588(5) Uani 1 1 d . . . . .
H1 H 0.5371 -0.0386 0.8046 0.071 Uiso 1 1 calc R U . . .
C2 C 0.6935(3) -0.06447(11) 0.9785(2) 0.0656(6) Uani 1 1 d . . . . .
H2 H 0.6643 -0.1115 0.9745 0.079 Uiso 1 1 calc R U . . .
C3 C 0.8123(3) -0.04075(12) 1.0871(2) 0.0608(6) Uani 1 1 d . . . . .
C4 C 0.8961(3) -0.08945(13) 1.1983(2) 0.0854(8) Uani 1 1 d . . . . .
H4A H 1.0102 -0.0765 1.2290 0.128 Uiso 1 1 calc R U . . .
H4B H 0.8888 -0.1366 1.1655 0.128 Uiso 1 1 calc R U . . .
H4C H 0.8426 -0.0862 1.2711 0.128 Uiso 1 1 calc R U . . .
C5 C 0.8513(3) 0.02903(12) 1.0891(2) 0.0725(6) Uani 1 1 d . . . . .
H5 H 0.9302 0.0468 1.1610 0.087 Uiso 1 1 calc R U . . .
C6 C 0.7765(3) 0.07336(11) 0.9870(2) 0.0625(6) Uani 1 1 d . . . . .
H6 H 0.8065 0.1203 0.9912 0.075 Uiso 1 1 calc R U . . .
C7 C 0.6575(2) 0.04945(9) 0.87832(17) 0.0465(5) Uani 1 1 d . . . . .
C8 C 0.5785(2) 0.09732(9) 0.77108(18) 0.0451(5) Uani 1 1 d . . . . .
C9 C 0.6138(3) 0.17358(10) 0.7706(2) 0.0635(6) Uani 1 1 d . . . . .
H9A H 0.7279 0.1819 0.7682 0.076 Uiso 1 1 calc R U . . .
H9B H 0.5921 0.1961 0.8492 0.076 Uiso 1 1 calc R U . . .
C10 C 0.4950(2) 0.20049(9) 0.6424(2) 0.0555(5) Uani 1 1 d . . . . .
C11 C 0.3643(3) 0.24822(11) 0.6752(2) 0.0766(7) Uani 1 1 d . . . . .
H11A H 0.2852 0.2603 0.5942 0.115 Uiso 1 1 calc R U . . .
H11B H 0.4159 0.2899 0.7174 0.115 Uiso 1 1 calc R U . . .
H11C H 0.3093 0.2246 0.7346 0.115 Uiso 1 1 calc R U . . .
C12 C 0.5840(2) 0.23816(10) 0.5481(2) 0.0655(6) Uani 1 1 d . . . . .
H12A H 0.5025 0.2492 0.4664 0.079 Uiso 1 1 calc R U . . .
H12B H 0.6257 0.2822 0.5894 0.079 Uiso 1 1 calc R U . . .
C13 C 0.7246(3) 0.20089(12) 0.5100(2) 0.0739(7) Uani 1 1 d . . . . .
C14 C 0.6834(4) 0.14345(15) 0.4088(3) 0.1104(10) Uani 1 1 d . . . . .
H14A H 0.7822 0.1285 0.3841 0.166 Uiso 1 1 calc R U . . .
H14B H 0.6052 0.1602 0.3310 0.166 Uiso 1 1 calc R U . . .
H14C H 0.6365 0.1048 0.4465 0.166 Uiso 1 1 calc R U . . .
C15 C 0.8789(3) 0.21946(17) 0.5627(3) 0.1071(9) Uani 1 1 d . . . . .
H15A H 0.9652 0.1967 0.5372 0.128 Uiso 1 1 calc R U . . .
H15B H 0.9014 0.2553 0.6254 0.128 Uiso 1 1 calc R U . . .
C16 C 0.2973(3) 0.12535(11) 0.4706(2) 0.0602(6) Uani 1 1 d . . . . .
C17 C 0.2320(3) 0.05334(12) 0.4372(2) 0.0795(7) Uani 1 1 d . . . . .
H17A H 0.1491 0.0543 0.3545 0.119 Uiso 1 1 calc R U . . .
H17B H 0.1842 0.0363 0.5074 0.119 Uiso 1 1 calc R U . . .
H17C H 0.3206 0.0231 0.4282 0.119 Uiso 1 1 calc R U . . .
N1 N 0.47072(18) 0.07617(7) 0.66723(15) 0.0485(4) Uani 1 1 d . . . . .
N2 N 0.41763(19) 0.13325(8) 0.58477(15) 0.0521(4) Uani 1 1 d . . . . .
O1 O 0.24620(19) 0.17561(8) 0.39828(16) 0.0839(5) 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
C1 C2 1.379(3) . ?
C1 C7 1.384(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C5 1.373(3) . ?
C3 C4 1.512(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.465(3) . ?
C8 N1 1.287(2) . ?
C8 C9 1.489(3) . ?
C9 C10 1.538(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.497(2) . ?
C10 C11 1.518(3) . ?
C10 C12 1.534(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.500(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C15 1.319(3) . ?
C13 C14 1.497(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C16 O1 1.228(2) . ?
C16 N2 1.360(2) . ?
C16 C17 1.491(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 N2 1.389(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 120.53(19) . . ?
C2 C1 H1 119.7 . . ?
C7 C1 H1 119.7 . . ?
C1 C2 C3 122.2(2) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C5 C3 C2 116.93(19) . . ?
C5 C3 C4 121.5(2) . . ?
C2 C3 C4 121.5(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 121.6(2) . . ?
C3 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C7 121.3(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C1 117.41(17) . . ?
C6 C7 C8 120.64(17) . . ?
C1 C7 C8 121.94(17) . . ?
N1 C8 C7 121.95(16) . . ?
N1 C8 C9 113.90(16) . . ?
C7 C8 C9 124.15(16) . . ?
C8 C9 C10 104.09(15) . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C10 C9 H9B 110.9 . . ?
H9A C9 H9B 109.0 . . ?
N2 C10 C11 109.94(16) . . ?
N2 C10 C12 112.35(17) . . ?
C11 C10 C12 109.70(16) . . ?
N2 C10 C9 100.43(14) . . ?
C11 C10 C9 111.11(18) . . ?
C12 C10 C9 113.03(17) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C10 117.78(16) . . ?
C13 C12 H12A 107.9 . . ?
C10 C12 H12A 107.9 . . ?
C13 C12 H12B 107.9 . . ?
C10 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
C15 C13 C14 121.6(3) . . ?
C15 C13 C12 120.6(3) . . ?
C14 C13 C12 117.8(2) . . ?
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 120.0 . . ?
C13 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
O1 C16 N2 120.95(19) . . ?
O1 C16 C17 121.95(19) . . ?
N2 C16 C17 117.10(18) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 N1 N2 108.54(14) . . ?
C16 N2 N1 120.18(16) . . ?
C16 N2 C10 126.71(15) . . ?
N1 N2 C10 112.89(14) . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_WYQ20210321
_database_code_depnum_ccdc_archive 'CCDC 2165846'
loop_
_audit_author_name
_audit_author_address
'Lei Wang'
;Yangzhou University
China
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N2 O3'
_chemical_formula_sum            'C22 H24 N2 O3'
_chemical_formula_weight         364.43

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      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                   12.2443(14)
_cell_length_b                   13.3482(15)
_cell_length_c                   11.9736(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.893(3)
_cell_angle_gamma                90
_cell_volume                     1956.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5046
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      23.68

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5740
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_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            19075
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.811
_diffrn_reflns_theta_max         25.999
_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             3832
_reflns_number_gt                2108
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0649P)²+0.3483P] 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         3832
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.24958(19) 0.99395(18) 1.07082(19) 0.0644(6) Uani 1 1 d . . . . .
H1 H 0.2104 1.0535 1.0739 0.077 Uiso 1 1 calc R U . . .
C2 C 0.2363(2) 0.9222(2) 1.15330(19) 0.0707(7) Uani 1 1 d . . . . .
H2 H 0.1883 0.9349 1.2110 0.085 Uiso 1 1 calc R U . . .
C3 C 0.2919(2) 0.83315(18) 1.15212(18) 0.0617(6) Uani 1 1 d . . . . .
C4 C 0.2790(3) 0.7563(2) 1.2424(2) 0.0876(9) Uani 1 1 d . . . . .
H4A H 0.3330 0.7674 1.3000 0.131 Uiso 1 1 calc R U . . .
H4B H 0.2884 0.6905 1.2115 0.131 Uiso 1 1 calc R U . . .
H4C H 0.2074 0.7617 1.2733 0.131 Uiso 1 1 calc R U . . .
C5 C 0.3636(2) 0.81782(16) 1.06526(19) 0.0623(6) Uani 1 1 d . . . . .
H5 H 0.4029 0.7583 1.0624 0.075 Uiso 1 1 calc R U . . .
C6 C 0.37782(19) 0.88817(15) 0.98359(18) 0.0561(6) Uani 1 1 d . . . . .
H6 H 0.4268 0.8756 0.9267 0.067 Uiso 1 1 calc R U . . .
C7 C 0.32062(17) 0.97762(15) 0.98410(17) 0.0505(5) Uani 1 1 d . . . . .
C8 C 0.33355(18) 1.05236(14) 0.89551(17) 0.0498(5) Uani 1 1 d . . . . .
C9 C 0.45810(18) 1.12460(17) 0.65359(19) 0.0569(6) Uani 1 1 d . . . . .
C10 C 0.5379(2) 1.04118(18) 0.6396(2) 0.0709(7) Uani 1 1 d . . . . .
H10A H 0.4993 0.9804 0.6224 0.106 Uiso 1 1 calc R U . . .
H10B H 0.5794 1.0325 0.7076 0.106 Uiso 1 1 calc R U . . .
H10C H 0.5863 1.0569 0.5798 0.106 Uiso 1 1 calc R U . . .
C11 C 0.2752(2) 1.15012(17) 0.88927(18) 0.0674(7) Uani 1 1 d . . . . .
H11A H 0.2969 1.1934 0.9508 0.081 Uiso 1 1 calc R U . . .
H11B H 0.1967 1.1404 0.8908 0.081 Uiso 1 1 calc R U . . .
C12 C 0.3099(2) 1.19464(15) 0.77725(18) 0.0589(6) Uani 1 1 d . . . . .
C13 C 0.3579(2) 1.29936(16) 0.7918(2) 0.0828(8) Uani 1 1 d . . . . .
H13A H 0.4172 1.2971 0.8452 0.124 Uiso 1 1 calc R U . . .
H13B H 0.3025 1.3441 0.8179 0.124 Uiso 1 1 calc R U . . .
H13C H 0.3843 1.3228 0.7214 0.124 Uiso 1 1 calc R U . . .
C14 C 0.21602(19) 1.19827(15) 0.68953(19) 0.0599(6) Uani 1 1 d . . . . .
H14A H 0.1579 1.2394 0.7190 0.072 Uiso 1 1 calc R U . . .
H14B H 0.2428 1.2314 0.6233 0.072 Uiso 1 1 calc R U . . .
C15 C 0.16820(18) 1.09913(16) 0.65514(17) 0.0532(6) Uani 1 1 d . . . . .
C16 C 0.0765(2) 1.06051(18) 0.7054(2) 0.0657(7) Uani 1 1 d . . . . .
H16 H 0.0430 1.0966 0.7618 0.079 Uiso 1 1 calc R U . . .
C17 C 0.0340(2) 0.96919(18) 0.6732(2) 0.0670(7) Uani 1 1 d . . . . .
H17 H -0.0275 0.9444 0.7084 0.080 Uiso 1 1 calc R U . . .
C18 C 0.08153(18) 0.91418(16) 0.58956(18) 0.0555(6) Uani 1 1 d . . . . .
C19 C 0.17178(18) 0.95308(18) 0.53743(18) 0.0612(6) Uani 1 1 d . . . . .
H19 H 0.2045 0.9174 0.4802 0.073 Uiso 1 1 calc R U . . .
C20 C 0.21358(19) 1.04424(17) 0.56955(19) 0.0607(6) Uani 1 1 d . . . . .
H20 H 0.2739 1.0697 0.5328 0.073 Uiso 1 1 calc R U . . .
C21 C 0.0345(2) 0.81529(19) 0.5596(2) 0.0650(7) Uani 1 1 d . . . . .
C22 C 0.0438(3) 0.67704(19) 0.4379(3) 0.0942(9) Uani 1 1 d . . . . .
H22A H 0.0390 0.6344 0.5022 0.141 Uiso 1 1 calc R U . . .
H22B H 0.0940 0.6485 0.3859 0.141 Uiso 1 1 calc R U . . .
H22C H -0.0269 0.6832 0.4029 0.141 Uiso 1 1 calc R U . . .
N1 N 0.40035(14) 1.03834(12) 0.81573(15) 0.0511(5) Uani 1 1 d . . . . .
N2 N 0.39499(15) 1.12121(12) 0.74487(14) 0.0531(5) Uani 1 1 d . . . . .
O1 O 0.44917(14) 1.19369(12) 0.58605(14) 0.0760(5) Uani 1 1 d . . . . .
O2 O -0.03787(18) 0.77527(15) 0.60846(18) 0.1045(7) Uani 1 1 d . . . . .
O3 O 0.08199(14) 0.77442(12) 0.47180(16) 0.0776(5) 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
C1 C7 1.382(3) . ?
C1 C2 1.387(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C3 C5 1.386(3) . ?
C3 C4 1.500(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.369(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.467(3) . ?
C8 N1 1.281(3) . ?
C8 C11 1.489(3) . ?
C9 O1 1.230(3) . ?
C9 N2 1.349(3) . ?
C9 C10 1.493(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.533(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.486(3) . ?
C12 C13 1.525(3) . ?
C12 C14 1.546(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.502(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.382(3) . ?
C15 C20 1.383(3) . ?
C16 C17 1.378(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(3) . ?
C18 C21 1.482(3) . ?
C19 C20 1.373(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O2 1.195(3) . ?
C21 O3 1.327(3) . ?
C22 O3 1.438(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 N2 1.395(2) . ?

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
C7 C1 C2 120.5(2) . . ?
C7 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 121.9(2) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C5 117.2(2) . . ?
C2 C3 C4 121.9(2) . . ?
C5 C3 C4 121.0(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C3 C5 H5 119.2 . . ?
C5 C6 C7 121.2(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C1 C7 C6 117.6(2) . . ?
C1 C7 C8 120.8(2) . . ?
C6 C7 C8 121.6(2) . . ?
N1 C8 C7 121.15(19) . . ?
N1 C8 C11 113.72(19) . . ?
C7 C8 C11 125.1(2) . . ?
O1 C9 N2 120.8(2) . . ?
O1 C9 C10 122.5(2) . . ?
N2 C9 C10 116.7(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 C12 104.11(18) . . ?
C8 C11 H11A 110.9 . . ?
C12 C11 H11A 110.9 . . ?
C8 C11 H11B 110.9 . . ?
C12 C11 H11B 110.9 . . ?
H11A C11 H11B 109.0 . . ?
N2 C12 C13 111.3(2) . . ?
N2 C12 C11 100.25(16) . . ?
C13 C12 C11 111.55(19) . . ?
N2 C12 C14 111.12(17) . . ?
C13 C12 C14 109.26(18) . . ?
C11 C12 C14 113.1(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 . . ?
C15 C14 C12 116.18(17) . . ?
C15 C14 H14A 108.2 . . ?
C12 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
C12 C14 H14B 108.2 . . ?
H14A C14 H14B 107.4 . . ?
C16 C15 C20 117.6(2) . . ?
C16 C15 C14 121.7(2) . . ?
C20 C15 C14 120.7(2) . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 118.6(2) . . ?
C17 C18 C21 118.9(2) . . ?
C19 C18 C21 122.5(2) . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C15 121.7(2) . . ?
C19 C20 H20 119.2 . . ?
C15 C20 H20 119.2 . . ?
O2 C21 O3 122.8(2) . . ?
O2 C21 C18 124.6(3) . . ?
O3 C21 C18 112.6(2) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 N1 N2 108.25(17) . . ?
C9 N2 N1 119.82(18) . . ?
C9 N2 C12 127.00(18) . . ?
N1 N2 C12 113.01(17) . . ?
C21 O3 C22 116.8(2) . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.037

