# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_exp_5321
_database_code_depnum_ccdc_archive 'CCDC 2165539'
loop_
_audit_author_name
_audit_author_address
GGG
;Inner Mongolia University
China
;
_audit_update_record             
;
2022-04-09 deposited with the CCDC.	2022-07-14 downloaded from the CCDC.
;
_audit_creation_date             2018-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   18.0493(10)
_cell_length_b                   8.6789(6)
_cell_length_c                   16.1121(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2523.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2260
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7180
_cell_measurement_theta_min      4.2170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10097
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.989
_diffrn_reflns_theta_min         3.494
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  34.00   1.00    5.00    --   15.49 -38.00  60.00   71
  2  ω    -88.00   4.00   1.00    5.00    --  -16.28 -19.00   0.00   92
  3  ω    -20.00  23.00   1.00    5.00    --  -16.28 -99.00  30.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0139382000
_diffrn_orient_matrix_UB_12      -0.0576504000
_diffrn_orient_matrix_UB_13      0.0269823000
_diffrn_orient_matrix_UB_21      -0.0014897000
_diffrn_orient_matrix_UB_22      -0.0545477000
_diffrn_orient_matrix_UB_23      -0.0327451000
_diffrn_orient_matrix_UB_31      0.0367398000
_diffrn_orient_matrix_UB_32      0.0196777000
_diffrn_orient_matrix_UB_33      -0.0115423000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2039
_reflns_number_total             2702
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2702
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0292P)²+2.7672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1564
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C9(H9), C4(H4), C12(H12), C7(H7), C15(H15), C14(H14), C6(H6),
 C13(H13), C5(H5)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44376(11) 0.1310(2) 0.70810(12) 0.0501(5) Uani 1 1 d . . . . .
N1 N 0.38371(12) 0.3697(3) 0.79528(14) 0.0417(6) Uani 1 1 d . . . . .
O2 O 0.38767(15) 0.4855(3) 0.92284(13) 0.0692(7) Uani 1 1 d . . . . .
C10 C 0.39988(14) 0.3890(3) 0.70806(16) 0.0391(6) Uani 1 1 d . . . . .
C8 C 0.36896(14) 0.2170(3) 0.82218(17) 0.0387(6) Uani 1 1 d . . . . .
C11 C 0.37680(15) 0.5360(3) 0.66914(16) 0.0404(6) Uani 1 1 d . . . . .
C3 C 0.39978(14) 0.0984(3) 0.77629(16) 0.0389(6) Uani 1 1 d . . . . .
C2 C 0.42832(15) 0.2702(4) 0.66769(17) 0.0443(7) Uani 1 1 d . . . . .
C16 C 0.42580(16) 0.6234(4) 0.62221(18) 0.0475(7) Uani 1 1 d . . . . .
H16 H 0.474726 0.591379 0.616747 0.057 Uiso 1 1 calc R . . . .
C9 C 0.39549(17) 0.4897(3) 0.84817(18) 0.0489(7) Uani 1 1 d . . . . .
H9 H 0.410817 0.582560 0.825056 0.059 Uiso 1 1 calc R . . . .
C4 C 0.38950(17) -0.0535(3) 0.79737(19) 0.0495(7) Uani 1 1 d . . . . .
H4 H 0.409687 -0.131816 0.765088 0.059 Uiso 1 1 calc R . . . .
C12 C 0.30409(15) 0.5890(4) 0.6774(2) 0.0493(7) Uani 1 1 d . . . . .
H12 H 0.270679 0.534784 0.710254 0.059 Uiso 1 1 calc R . . . .
C7 C 0.32616(16) 0.1807(4) 0.89072(18) 0.0489(7) Uani 1 1 d . . . . .
H7 H 0.303623 0.258469 0.921362 0.059 Uiso 1 1 calc R . . . .
C15 C 0.40287(18) 0.7573(4) 0.58352(19) 0.0587(8) Uani 1 1 d . . . . .
H15 H 0.436474 0.815231 0.552844 0.070 Uiso 1 1 calc R . . . .
C14 C 0.33074(19) 0.8049(4) 0.5903(2) 0.0601(9) Uani 1 1 d . . . . .
H14 H 0.314981 0.893711 0.563179 0.072 Uiso 1 1 calc R . . . .
C6 C 0.31703(18) 0.0278(4) 0.9135(2) 0.0578(8) Uani 1 1 d . . . . .
H6 H 0.289291 0.003279 0.960294 0.069 Uiso 1 1 calc R . . . .
C13 C 0.28167(18) 0.7204(4) 0.6375(2) 0.0593(9) Uani 1 1 d . . . . .
H13 H 0.232768 0.752948 0.642247 0.071 Uiso 1 1 calc R . . . .
C5 C 0.34869(18) -0.0876(4) 0.8673(2) 0.0590(9) Uani 1 1 d . . . . .
H5 H 0.342544 -0.189765 0.883320 0.071 Uiso 1 1 calc R . . . .
C1 C 0.44597(19) 0.2581(5) 0.57808(19) 0.0654(10) Uani 1 1 d . . . . .
H1A H 0.498715 0.253072 0.570924 0.098 Uiso 1 1 calc GR . . . .
H1B H 0.426943 0.346710 0.549513 0.098 Uiso 1 1 calc GR . . . .
H1C H 0.423672 0.166583 0.555774 0.098 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.385(3) . ?
O1 C2 1.401(4) . ?
N1 C10 1.445(3) . ?
N1 C8 1.419(4) . ?
N1 C9 1.363(3) . ?
O2 C9 1.212(3) . ?
C10 C11 1.482(4) . ?
C10 C2 1.323(4) . ?
C8 C3 1.384(4) . ?
C8 C7 1.384(4) . ?
C11 C16 1.389(4) . ?
C11 C12 1.397(4) . ?
C3 C4 1.374(4) . ?
C2 C1 1.482(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.382(4) . ?
C9 H9 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.378(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.387(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.370(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.379(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.372(4) . ?
C13 H13 0.9300 . ?
C5 H5 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C3 O1 C2 115.5(2) . . ?
C8 N1 C10 116.3(2) . . ?
C9 N1 C10 119.2(2) . . ?
C9 N1 C8 123.5(2) . . ?
N1 C10 C11 117.0(2) . . ?
C2 C10 N1 117.8(3) . . ?
C2 C10 C11 124.9(2) . . ?
C3 C8 N1 117.1(2) . . ?
C7 C8 N1 124.1(3) . . ?
C7 C8 C3 118.8(3) . . ?
C16 C11 C10 121.5(2) . . ?
C16 C11 C12 118.0(3) . . ?
C12 C11 C10 120.5(3) . . ?
C8 C3 O1 120.2(3) . . ?
C4 C3 O1 118.0(2) . . ?
C4 C3 C8 121.8(3) . . ?
O1 C2 C1 110.4(3) . . ?
C10 C2 O1 121.4(2) . . ?
C10 C2 C1 128.2(3) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 H16 119.5 . . ?
N1 C9 H9 117.3 . . ?
O2 C9 N1 125.4(3) . . ?
O2 C9 H9 117.3 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.7(3) . . ?
C5 C4 H4 120.6 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C8 C7 H7 120.2 . . ?
C8 C7 C6 119.7(3) . . ?
C6 C7 H7 120.2 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C15 C14 H14 120.2 . . ?
C15 C14 C13 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_olex2_date_sample_data_collection 1523676535.97
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.377
_oxdiff_exptl_absorpt_empirical_full_min 0.797
####################################################################### 
# 
# 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_170605a_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 2165545'
loop_
_audit_author_name
_audit_author_address
iii
;Inner Mongolia University
China
;
_audit_update_record             
;
2022-04-09 deposited with the CCDC.	2022-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 N O2'
_chemical_formula_weight         327.37

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.6932(5)
_cell_length_b                   10.1353(5)
_cell_length_c                   18.2929(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.155(3)
_cell_angle_gamma                90.00
_cell_volume                     1707.69(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      28.30

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37636
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         28.36
_reflns_number_total             4245
_reflns_number_gt                3244
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0544P)²+0.3873P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4245
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.08695(10) 0.77156(9) 0.82231(6) 0.0518(2) Uani 1 1 d . . .
O2 O -0.33194(11) 1.02802(12) 0.73100(6) 0.0671(3) Uani 1 1 d . . .
N1 N -0.11825(10) 0.95760(11) 0.81614(6) 0.0426(2) Uani 1 1 d . . .
C1 C 0.43589(18) 0.7029(2) 1.10925(11) 0.0753(5) Uani 1 1 d . . .
H1 H 0.4675 0.6606 1.1567 0.090 Uiso 1 1 calc R . .
C2 C 0.40581(19) 0.63149(18) 1.04300(12) 0.0760(5) Uani 1 1 d . . .
H2 H 0.4163 0.5402 1.0454 0.091 Uiso 1 1 calc R . .
C3 C 0.35977(16) 0.69349(15) 0.97213(10) 0.0610(4) Uani 1 1 d . . .
H3 H 0.3405 0.6437 0.9274 0.073 Uiso 1 1 calc R . .
C4 C 0.34219(12) 0.82901(13) 0.96741(8) 0.0449(3) Uani 1 1 d . . .
C5 C 0.29150(13) 0.89967(15) 0.89089(8) 0.0504(3) Uani 1 1 d . . .
H5A H 0.3225 0.9910 0.8983 0.060 Uiso 1 1 calc R . .
H5B H 0.3373 0.8597 0.8562 0.060 Uiso 1 1 calc R . .
C6 C 0.12977(13) 0.89530(13) 0.85453(7) 0.0422(3) Uani 1 1 d . . .
C7 C 0.03294(12) 0.98849(12) 0.85286(7) 0.0391(3) Uani 1 1 d . . .
C8 C 0.06452(12) 1.11966(12) 0.89073(7) 0.0397(3) Uani 1 1 d . . .
C9 C -0.01036(15) 1.15808(14) 0.94098(8) 0.0497(3) Uani 1 1 d . . .
H9 H -0.0794 1.1020 0.9498 0.060 Uiso 1 1 calc R . .
C10 C 0.01706(19) 1.27844(16) 0.97770(9) 0.0616(4) Uani 1 1 d . . .
H10 H -0.0341 1.3035 1.0108 0.074 Uiso 1 1 calc R . .
C11 C 0.11988(19) 1.36168(16) 0.96549(10) 0.0665(4) Uani 1 1 d . . .
H11 H 0.1394 1.4422 0.9910 0.080 Uiso 1 1 calc R . .
C12 C -0.3194(2) 0.6448(2) 0.81852(10) 0.0732(5) Uani 1 1 d . . .
H12 H -0.4110 0.6151 0.8172 0.088 Uiso 1 1 calc R . .
C13 C -0.29311(16) 0.77901(17) 0.81762(9) 0.0595(4) Uani 1 1 d . . .
H13 H -0.3657 0.8395 0.8168 0.071 Uiso 1 1 calc R . .
C14 C -0.15681(14) 0.82213(13) 0.81789(7) 0.0447(3) Uani 1 1 d . . .
C15 C 0.19382(16) 1.32538(15) 0.91537(10) 0.0608(4) Uani 1 1 d . . .
H15 H 0.2629 1.3819 0.9069 0.073 Uiso 1 1 calc R . .
C16 C 0.16607(14) 1.20545(13) 0.87751(8) 0.0474(3) Uani 1 1 d . . .
H16 H 0.2154 1.1822 0.8432 0.057 Uiso 1 1 calc R . .
C17 C 0.41932(17) 0.8374(2) 1.10560(10) 0.0696(5) Uani 1 1 d . . .
H17 H 0.4399 0.8864 1.1507 0.084 Uiso 1 1 calc R . .
C18 C 0.37210(15) 0.90044(16) 1.03504(9) 0.0557(4) Uani 1 1 d . . .
H18 H 0.3604 0.9916 1.0331 0.067 Uiso 1 1 calc R . .
C19 C -0.05002(14) 0.73074(13) 0.82124(7) 0.0453(3) Uani 1 1 d . . .
C20 C -0.07568(19) 0.59695(15) 0.82322(8) 0.0588(4) Uani 1 1 d . . .
H20 H -0.0023 0.5363 0.8258 0.071 Uiso 1 1 calc R . .
C21 C -0.2115(2) 0.55501(18) 0.82132(10) 0.0715(5) Uani 1 1 d . . .
H21 H -0.2306 0.4652 0.8219 0.086 Uiso 1 1 calc R . .
C22 C -0.20807(14) 1.04862(15) 0.77063(8) 0.0489(3) Uani 1 1 d . . .
H22 H -0.1715 1.1333 0.7699 0.059 Uiso 1 1 calc R . .


_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 C19 1.3849(16) . ?
O1 C6 1.3929(16) . ?
O2 C22 1.2118(16) . ?
N1 C22 1.3604(17) . ?
N1 C14 1.4259(17) . ?
N1 C7 1.4434(14) . ?
C1 C2 1.363(3) . ?
C1 C17 1.372(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9300 . ?
C4 C18 1.384(2) . ?
C4 C5 1.5116(19) . ?
C5 C6 1.5008(17) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.3251(18) . ?
C7 C8 1.4862(17) . ?
C8 C16 1.3899(18) . ?
C8 C9 1.3925(18) . ?
C9 C10 1.378(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(2) . ?
C10 H10 0.9300 . ?
C11 C15 1.378(2) . ?
C11 H11 0.9300 . ?
C12 C21 1.376(3) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.3901(19) . ?
C13 H13 0.9300 . ?
C14 C19 1.376(2) . ?
C15 C16 1.383(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.381(2) . ?
C20 C21 1.373(2) . ?
C20 H20 0.9300 . ?
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
C19 O1 C6 115.65(10) . . ?
C22 N1 C14 122.99(11) . . ?
C22 N1 C7 120.07(11) . . ?
C14 N1 C7 115.70(10) . . ?
C2 C1 C17 119.66(16) . . ?
C2 C1 H1 120.2 . . ?
C17 C1 H1 120.2 . . ?
C1 C2 C3 120.63(17) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 120.46(16) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C18 118.43(14) . . ?
C3 C4 C5 121.76(13) . . ?
C18 C4 C5 119.81(13) . . ?
C6 C5 C4 112.93(11) . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 O1 121.09(11) . . ?
C7 C6 C5 128.59(12) . . ?
O1 C6 C5 110.27(11) . . ?
C6 C7 N1 117.73(11) . . ?
C6 C7 C8 125.82(10) . . ?
N1 C7 C8 116.28(10) . . ?
C16 C8 C9 118.88(12) . . ?
C16 C8 C7 122.18(12) . . ?
C9 C8 C7 118.94(11) . . ?
C10 C9 C8 120.55(13) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.20(15) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C15 119.83(14) . . ?
C10 C11 H11 120.1 . . ?
C15 C11 H11 120.1 . . ?
C21 C12 C13 120.62(16) . . ?
C21 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 119.16(16) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C19 C14 C13 119.30(13) . . ?
C19 C14 N1 116.76(11) . . ?
C13 C14 N1 123.93(13) . . ?
C11 C15 C16 120.49(14) . . ?
C11 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C8 120.02(14) . . ?
C15 C16 H16 120.0 . . ?
C8 C16 H16 120.0 . . ?
C1 C17 C18 120.25(17) . . ?
C1 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C4 120.57(16) . . ?
C17 C18 H18 119.7 . . ?
C4 C18 H18 119.7 . . ?
C14 C19 C20 121.52(13) . . ?
C14 C19 O1 120.27(12) . . ?
C20 C19 O1 118.21(13) . . ?
C21 C20 C19 118.83(16) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C12 120.54(16) . . ?
C20 C21 H21 119.7 . . ?
C12 C21 H21 119.7 . . ?
O2 C22 N1 125.11(14) . . ?
O2 C22 H22 117.4 . . ?
N1 C22 H22 117.4 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033
