# 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_20181222_mdl_zhp_ch9_67
_database_code_depnum_ccdc_archive 'CCDC 1938292'
loop_
_audit_author_name
_audit_author_address
'Dong-Liang Mo'
;Guangxi Normal University
China
;
_audit_update_record             
;
2019-07-04 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.57(C18 H18 N2 O3)'
_chemical_formula_sum            'C11 H10 N O'
_chemical_formula_weight         172.20
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.014(2)
_cell_length_b                   10.0228(11)
_cell_length_c                   21.573(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3246.5(9)
_cell_formula_units_Z            14
_cell_measurement_reflns_used    1041
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.1890
_cell_measurement_theta_min      3.8650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1274
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11068
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.946
_diffrn_reflns_theta_min         3.306
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  57.00   1.00   10.00    --   17.61  77.00 150.00   69
  2  ω    -86.00  23.00   1.00   10.00    --  -19.80 -19.00   0.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0192021000
_diffrn_orient_matrix_UB_12      0.0030643000
_diffrn_orient_matrix_UB_13      -0.0300338000
_diffrn_orient_matrix_UB_21      -0.0419370000
_diffrn_orient_matrix_UB_22      0.0181526000
_diffrn_orient_matrix_UB_23      -0.0125614000
_diffrn_orient_matrix_UB_31      0.0103373000
_diffrn_orient_matrix_UB_32      0.0682769000
_diffrn_orient_matrix_UB_33      0.0046471000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1287
_reflns_number_total             3794
_reflns_odcompleteness_completeness 99.60
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3794
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2084
_refine_ls_R_factor_gt           0.0871
_refine_ls_restrained_S_all      1.018
_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)+(0.1206P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2286
_refine_ls_wR_factor_ref         0.3103
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C12(H12), C6(H6), C3(H3), C10(H10), C9(H9), C4(H4), C5(H5), C11(H11)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_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
O2 O 0.24312(19) 0.4715(2) 0.07639(18) 0.0891(12) Uani 1 1 d . . . . .
O1 O 0.4073(2) 0.2254(3) 0.12061(15) 0.0813(10) Uani 1 1 d . . . . .
N2 N 0.2418(2) 0.2490(3) 0.07644(19) 0.0705(11) Uani 1 1 d . . . . .
H2 H 0.2701 0.1756 0.0825 0.085 Uiso 1 1 calc R . . . .
C17 C 0.2800(3) 0.3651(4) 0.0882(2) 0.0621(12) Uani 1 1 d . . . . .
O3 O 0.1554(2) 0.2479(3) 0.0541(2) 0.0835(11) Uani 1 1 d . . . . .
N1 N 0.3708(3) 0.1665(4) 0.17145(19) 0.0765(11) Uani 1 1 d . . . . .
C1 C 0.4038(3) 0.0426(4) 0.1783(2) 0.0768(14) Uani 1 1 d . . . . .
C15 C 0.3735(3) 0.3636(3) 0.1153(2) 0.0643(12) Uani 1 1 d . . . . .
C8 C 0.4214(3) -0.1587(4) 0.2273(2) 0.0727(13) Uani 1 1 d . . . . .
C7 C 0.4806(3) -0.1582(4) 0.1744(2) 0.0743(14) Uani 1 1 d . . . . .
C13 C 0.3742(4) -0.0348(5) 0.2306(3) 0.0780(14) Uani 1 1 d . . . . .
C12 C 0.3153(4) -0.0120(5) 0.2775(3) 0.0918(16) Uani 1 1 d . . . . .
H12 H 0.2849 0.0687 0.2796 0.110 Uiso 1 1 calc R . . . .
C6 C 0.5390(4) -0.2530(5) 0.1529(3) 0.0875(16) Uani 1 1 d . . . . .
H6 H 0.5464 -0.3330 0.1741 0.105 Uiso 1 1 calc R . . . .
C14 C 0.3765(3) 0.4399(4) 0.1755(2) 0.0834(15) Uani 1 1 d . . . . .
H14A H 0.3369 0.3991 0.2048 0.125 Uiso 1 1 calc GR . . . .
H14B H 0.3585 0.5305 0.1683 0.125 Uiso 1 1 calc GR . . . .
H14C H 0.4361 0.4387 0.1916 0.125 Uiso 1 1 calc GR . . . .
C2 C 0.4686(3) -0.0336(5) 0.1436(2) 0.0773(14) Uani 1 1 d . . . . .
C16 C 0.4361(3) 0.4216(4) 0.0684(2) 0.0845(15) Uani 1 1 d . . . . .
H16A H 0.4948 0.4275 0.0859 0.127 Uiso 1 1 calc GR . . . .
H16B H 0.4161 0.5092 0.0568 0.127 Uiso 1 1 calc GR . . . .
H16C H 0.4376 0.3654 0.0323 0.127 Uiso 1 1 calc GR . . . .
C3 C 0.5168(4) -0.0119(5) 0.0918(3) 0.0916(16) Uani 1 1 d . . . . .
H3 H 0.5101 0.0693 0.0715 0.110 Uiso 1 1 calc R . . . .
C10 C 0.3459(5) -0.2256(7) 0.3186(3) 0.107(2) Uani 1 1 d . . . . .
H10 H 0.3357 -0.2897 0.3490 0.129 Uiso 1 1 calc R . . . .
C18 C 0.1583(4) 0.2438(6) -0.0107(3) 0.123(2) Uani 1 1 d . . . . .
H18A H 0.0987 0.2401 -0.0268 0.184 Uiso 1 1 calc GR . . . .
H18B H 0.1906 0.1661 -0.0238 0.184 Uiso 1 1 calc GR . . . .
H18C H 0.1875 0.3224 -0.0260 0.184 Uiso 1 1 calc GR . . . .
C9 C 0.4059(4) -0.2515(5) 0.2720(3) 0.0885(16) Uani 1 1 d . . . . .
H9 H 0.4360 -0.3327 0.2711 0.106 Uiso 1 1 calc R . . . .
C4 C 0.5755(4) -0.1037(6) 0.0673(3) 0.1001(17) Uani 1 1 d . . . . .
H4 H 0.6069 -0.0858 0.0310 0.120 Uiso 1 1 calc R . . . .
C5 C 0.5865(4) -0.2277(6) 0.0996(3) 0.1056(19) Uani 1 1 d . . . . .
H5 H 0.6259 -0.2914 0.0844 0.127 Uiso 1 1 calc R . . . .
C11 C 0.3010(5) -0.1071(8) 0.3211(3) 0.117(2) Uani 1 1 d . . . . .
H11 H 0.2604 -0.0916 0.3529 0.140 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
O2 C17 1.228(4) . ?
O1 N1 1.361(4) . ?
O1 C15 1.480(4) . ?
N2 C17 1.322(4) . ?
N2 O3 1.383(4) . ?
C17 C15 1.521(6) . ?
O3 C18 1.401(7) . ?
N1 C1 1.345(6) . ?
C1 C13 1.438(7) . ?
C1 C2 1.446(7) . ?
C15 C14 1.507(6) . ?
C15 C16 1.499(6) . ?
C8 C7 1.446(7) . ?
C8 C13 1.432(6) . ?
C8 C9 1.360(7) . ?
C7 C6 1.374(7) . ?
C7 C2 1.426(6) . ?
C13 C12 1.364(7) . ?
C12 C11 1.357(7) . ?
C6 C5 1.377(8) . ?
C2 C3 1.349(7) . ?
C3 C4 1.380(7) . ?
C10 C9 1.374(8) . ?
C10 C11 1.367(8) . ?
C4 C5 1.434(7) . ?

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
N1 O1 C15 109.3(3) . . ?
C17 N2 O3 118.7(3) . . ?
O2 C17 N2 121.9(4) . . ?
O2 C17 C15 120.3(3) . . ?
N2 C17 C15 117.7(3) . . ?
N2 O3 C18 108.6(4) . . ?
C1 N1 O1 109.9(4) . . ?
N1 C1 C13 118.1(5) . . ?
N1 C1 C2 132.7(5) . . ?
C13 C1 C2 109.2(4) . . ?
O1 C15 C17 110.8(3) . . ?
O1 C15 C14 113.5(3) . . ?
O1 C15 C16 101.6(3) . . ?
C14 C15 C17 110.7(4) . . ?
C16 C15 C17 108.3(4) . . ?
C16 C15 C14 111.5(4) . . ?
C13 C8 C7 109.8(4) . . ?
C9 C8 C7 131.9(5) . . ?
C9 C8 C13 118.3(6) . . ?
C6 C7 C8 131.0(4) . . ?
C6 C7 C2 121.9(5) . . ?
C2 C7 C8 107.1(4) . . ?
C8 C13 C1 106.1(5) . . ?
C12 C13 C1 133.7(5) . . ?
C12 C13 C8 120.2(5) . . ?
C11 C12 C13 120.0(6) . . ?
C7 C6 C5 119.1(5) . . ?
C7 C2 C1 107.8(5) . . ?
C3 C2 C1 134.8(5) . . ?
C3 C2 C7 117.4(5) . . ?
C2 C3 C4 123.6(5) . . ?
C11 C10 C9 121.1(6) . . ?
C8 C9 C10 120.1(5) . . ?
C3 C4 C5 117.7(6) . . ?
C6 C5 C4 120.4(6) . . ?
C12 C11 C10 120.3(7) . . ?

_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 1.808
_oxdiff_exptl_absorpt_empirical_full_min 0.408
####################################################################### 
# 
# 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_20180718_MDL_ZHP_CCH_8_53
_database_code_depnum_ccdc_archive 'CCDC 1938293'
loop_
_audit_author_name
_audit_author_address
'Dong-Liang Mo'
;Guangxi Normal University
China
;
_audit_update_record             
;
2019-07-04 deposited with the CCDC.	2020-09-25 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         ?
_chemical_formula_sum            'C17 H16 N2 O2'
_chemical_formula_weight         280.32

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                   11.2384(6)
_cell_length_b                   10.3430(5)
_cell_length_c                   13.5036(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.740(6)
_cell_angle_gamma                90
_cell_volume                     1494.99(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3082
_cell_measurement_theta_min      3.633
_cell_measurement_theta_max      28.339

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.981
_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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11821
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.442
_diffrn_reflns_theta_max         29.059
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3611
_reflns_number_gt                2519
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0576P)²+0.6626P] 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         3611
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1658
_refine_ls_wR_factor_gt          0.1497
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.30436(12) 0.83661(14) 0.04972(11) 0.0530(4) Uani 1 1 d . . . . .
N2 N 0.19816(15) 0.76628(17) 0.05126(13) 0.0500(4) Uani 1 1 d . . . . .
C3 C 0.09842(16) 0.81417(19) -0.01505(14) 0.0429(4) Uani 1 1 d . . . . .
C4 C -0.11604(17) 0.8251(2) -0.09708(15) 0.0459(5) Uani 1 1 d . . . . .
O5 O 0.52457(16) 0.57843(16) 0.12793(12) 0.0692(5) Uani 1 1 d . . . . .
N6 N 0.39638(16) 0.63770(19) -0.02764(13) 0.0567(5) Uani 1 1 d . . . . .
H6A H 0.4166 0.5721 -0.0582 0.068 Uiso 1 1 calc R U . . .
H6B H 0.3428 0.6928 -0.0629 0.068 Uiso 1 1 calc R U . . .
C7 C 0.07459(17) 0.91921(19) -0.09190(14) 0.0433(4) Uani 1 1 d . . . . .
C8 C -0.02428(18) 0.7573(2) -0.02165(15) 0.0473(5) Uani 1 1 d . . . . .
C9 C -0.05512(17) 0.92445(19) -0.14147(14) 0.0447(4) Uani 1 1 d . . . . .
C10 C 0.41478(18) 0.7773(2) 0.12105(16) 0.0522(5) Uani 1 1 d . . . . .
C11 C 0.44773(17) 0.6538(2) 0.07374(15) 0.0464(5) Uani 1 1 d . . . . .
C12 C 0.1539(2) 1.0028(2) -0.12066(19) 0.0614(6) Uani 1 1 d . . . . .
H12 H 0.2397 0.9999 -0.0882 0.074 Uiso 1 1 calc R U . . .
C13 C -0.2400(2) 0.7917(3) -0.11813(19) 0.0641(6) Uani 1 1 d . . . . .
H13 H -0.3019 0.8367 -0.1677 0.077 Uiso 1 1 calc R U . . .
C14 C -0.1045(2) 1.0132(2) -0.21882(18) 0.0630(6) Uani 1 1 d . . . . .
H14 H -0.1902 1.0172 -0.2515 0.076 Uiso 1 1 calc R U . . .
C15 C 0.3984(2) 0.7506(3) 0.22576(17) 0.0791(9) Uani 1 1 d . . . . .
H15A H 0.3768 0.8293 0.2539 0.119 Uiso 1 1 calc R U . . .
H15B H 0.4750 0.7172 0.2719 0.119 Uiso 1 1 calc R U . . .
H15C H 0.3330 0.6882 0.2183 0.119 Uiso 1 1 calc R U . . .
C16 C -0.0550(2) 0.6565(3) 0.0320(2) 0.0705(7) Uani 1 1 d . . . . .
H16 H 0.0062 0.6116 0.0823 0.085 Uiso 1 1 calc R U . . .
C17 C -0.0245(3) 1.0961(3) -0.2469(2) 0.0836(8) Uani 1 1 d . . . . .
H17 H -0.0567 1.1567 -0.2991 0.100 Uiso 1 1 calc R U . . .
C18 C 0.1028(3) 1.0906(3) -0.1988(2) 0.0824(8) Uani 1 1 d . . . . .
H18 H 0.1550 1.1472 -0.2194 0.099 Uiso 1 1 calc R U . . .
C19 C 0.5170(2) 0.8761(3) 0.1267(3) 0.0877(9) Uani 1 1 d . . . . .
H19A H 0.5219 0.8923 0.0580 0.132 Uiso 1 1 calc R U . . .
H19B H 0.5957 0.8432 0.1697 0.132 Uiso 1 1 calc R U . . .
H19C H 0.4980 0.9552 0.1558 0.132 Uiso 1 1 calc R U . . .
C20 C -0.2703(2) 0.6903(3) -0.0642(2) 0.0861(9) Uani 1 1 d . . . . .
H20 H -0.3536 0.6666 -0.0778 0.103 Uiso 1 1 calc R U . . .
C21 C -0.1794(3) 0.6236(3) 0.0094(2) 0.0897(9) Uani 1 1 d . . . . .
H21 H -0.2021 0.5552 0.0445 0.108 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 N2 1.403(2) . ?
O1 C10 1.454(2) . ?
N2 C3 1.301(2) . ?
C3 C7 1.470(3) . ?
C3 C8 1.477(3) . ?
C4 C13 1.378(3) . ?
C4 C8 1.397(3) . ?
C4 C9 1.461(3) . ?
O5 C11 1.226(2) . ?
N6 C11 1.324(2) . ?
C7 C12 1.379(3) . ?
C7 C9 1.408(3) . ?
C8 C16 1.373(3) . ?
C9 C14 1.374(3) . ?
C10 C15 1.506(3) . ?
C10 C19 1.523(3) . ?
C10 C11 1.524(3) . ?
C12 C18 1.378(3) . ?
C13 C20 1.377(4) . ?
C14 C17 1.377(4) . ?
C16 C21 1.379(3) . ?
C17 C18 1.380(4) . ?
C20 C21 1.374(4) . ?

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
N2 O1 C10 109.23(15) . . ?
C3 N2 O1 110.54(16) . . ?
N2 C3 C7 134.51(18) . . ?
N2 C3 C8 118.87(18) . . ?
C7 C3 C8 106.62(15) . . ?
C13 C4 C8 120.0(2) . . ?
C13 C4 C9 131.47(19) . . ?
C8 C4 C9 108.54(17) . . ?
C12 C7 C9 120.42(19) . . ?
C12 C7 C3 131.88(18) . . ?
C9 C7 C3 107.68(16) . . ?
C16 C8 C4 121.15(19) . . ?
C16 C8 C3 130.65(19) . . ?
C4 C8 C3 108.20(17) . . ?
C14 C9 C7 120.5(2) . . ?
C14 C9 C4 130.59(19) . . ?
C7 C9 C4 108.95(17) . . ?
O1 C10 C15 112.06(17) . . ?
O1 C10 C19 103.21(18) . . ?
C15 C10 C19 112.5(2) . . ?
O1 C10 C11 110.08(16) . . ?
C15 C10 C11 110.8(2) . . ?
C19 C10 C11 107.91(19) . . ?
O5 C11 N6 122.88(19) . . ?
O5 C11 C10 119.98(17) . . ?
N6 C11 C10 116.99(18) . . ?
C18 C12 C7 118.3(2) . . ?
C20 C13 C4 118.6(2) . . ?
C9 C14 C17 118.6(2) . . ?
C8 C16 C21 118.1(2) . . ?
C14 C17 C18 121.0(2) . . ?
C12 C18 C17 121.2(2) . . ?
C21 C20 C13 121.0(2) . . ?
C20 C21 C16 121.1(3) . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038



