# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_XSJ20230719
_database_code_depnum_ccdc_archive 'CCDC 2309689'
loop_
_audit_author_name
_audit_author_address
'Lei Wang'
;Yangzhou university
China
;
_audit_update_record             
;
2023-11-22 deposited with the CCDC.	2024-03-22 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         'C25 H21 N O'
_chemical_formula_sum            'C25 H21 N O'
_chemical_formula_weight         351.43

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                   20.259(6)
_cell_length_b                   8.444(2)
_cell_length_c                   11.524(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.245(9)
_cell_angle_gamma                90
_cell_volume                     1951.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3409
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      21.16

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5849
_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            26292
_diffrn_reflns_av_unetI/netI     0.1273
_diffrn_reflns_av_R_equivalents  0.1530
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.617
_diffrn_reflns_theta_max         26.000
_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             3823
_reflns_number_gt                1616
_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)+(0.0657P)²+0.5987P] 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         3823
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2137
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.1922
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.8692(2) 0.7150(5) 0.6010(4) 0.0910(13) Uani 1 1 d . . . . .
H1 H 0.8570 0.6445 0.5397 0.109 Uiso 1 1 calc R U . . .
C2 C 0.9353(2) 0.7296(6) 0.6470(6) 0.1176(17) Uani 1 1 d . . . . .
H2 H 0.9674 0.6692 0.6173 0.141 Uiso 1 1 calc R U . . .
C3 C 0.9537(3) 0.8344(8) 0.7374(6) 0.129(2) Uani 1 1 d . . . . .
H3 H 0.9984 0.8449 0.7689 0.155 Uiso 1 1 calc R U . . .
C4 C 0.9064(3) 0.9229(7) 0.7807(4) 0.1231(18) Uani 1 1 d . . . . .
H4 H 0.9188 0.9934 0.8420 0.148 Uiso 1 1 calc R U . . .
C5 C 0.84031(19) 0.9074(5) 0.7335(4) 0.0918(13) Uani 1 1 d . . . . .
H5 H 0.8085 0.9691 0.7629 0.110 Uiso 1 1 calc R U . . .
C6 C 0.82041(16) 0.8032(4) 0.6441(3) 0.0616(9) Uani 1 1 d . . . . .
C7 C 0.75037(15) 0.7895(4) 0.5947(3) 0.0549(9) Uani 1 1 d . . . . .
C8 C 0.69597(15) 0.8986(4) 0.6179(3) 0.0802(12) Uani 1 1 d . . . . .
H8A H 0.7033 1.0049 0.5904 0.096 Uiso 1 1 calc R U . . .
H8B H 0.6923 0.9025 0.7008 0.096 Uiso 1 1 calc R U . . .
C9 C 0.63462(15) 0.8248(4) 0.5486(3) 0.0559(9) Uani 1 1 d . . . . .
C10 C 0.58656(18) 0.7603(4) 0.6260(3) 0.0848(12) Uani 1 1 d . . . . .
H10A H 0.5522 0.7006 0.5792 0.127 Uiso 1 1 calc R U . . .
H10B H 0.5668 0.8466 0.6630 0.127 Uiso 1 1 calc R U . . .
H10C H 0.6102 0.6929 0.6850 0.127 Uiso 1 1 calc R U . . .
C11 C 0.60135(15) 0.9344(4) 0.4538(3) 0.0631(9) Uani 1 1 d . . . . .
H11A H 0.5927 1.0351 0.4891 0.076 Uiso 1 1 calc R U . . .
H11B H 0.6319 0.9537 0.3979 0.076 Uiso 1 1 calc R U . . .
C12 C 0.53802(19) 0.8725(4) 0.3901(3) 0.0634(10) Uani 1 1 d . . . . .
C13 C 0.48508(19) 0.8278(4) 0.3404(3) 0.0656(10) Uani 1 1 d . . . . .
C14 C 0.41968(16) 0.7881(4) 0.2820(3) 0.0562(9) Uani 1 1 d . . . . .
C15 C 0.38048(19) 0.6778(4) 0.3286(3) 0.0659(10) Uani 1 1 d . . . . .
H15 H 0.3980 0.6233 0.3962 0.079 Uiso 1 1 calc R U . . .
C16 C 0.31586(18) 0.6462(4) 0.2774(3) 0.0656(10) Uani 1 1 d . . . . .
H16 H 0.2907 0.5723 0.3118 0.079 Uiso 1 1 calc R U . . .
C17 C 0.28771(16) 0.7231(3) 0.1748(3) 0.0488(8) Uani 1 1 d . . . . .
C18 C 0.32834(16) 0.8320(4) 0.1294(3) 0.0553(9) Uani 1 1 d . . . . .
H18 H 0.3115 0.8861 0.0613 0.066 Uiso 1 1 calc R U . . .
C19 C 0.39269(16) 0.8637(4) 0.1809(3) 0.0594(9) Uani 1 1 d . . . . .
H19 H 0.4181 0.9373 0.1466 0.071 Uiso 1 1 calc R U . . .
C20 C 0.21880(16) 0.6929(4) 0.1173(3) 0.0546(9) Uani 1 1 d . . . . .
C21 C 0.1807(2) 0.5728(5) 0.1518(4) 0.1066(15) Uani 1 1 d . . . . .
H21 H 0.1986 0.5078 0.2135 0.128 Uiso 1 1 calc R U . . .
C22 C 0.1165(3) 0.5451(6) 0.0979(5) 0.1252(18) Uani 1 1 d . . . . .
H22 H 0.0922 0.4624 0.1243 0.150 Uiso 1 1 calc R U . . .
C23 C 0.0886(2) 0.6340(6) 0.0093(5) 0.0995(14) Uani 1 1 d . . . . .
H23 H 0.0451 0.6153 -0.0262 0.119 Uiso 1 1 calc R U . . .
C24 C 0.1253(2) 0.7522(6) -0.0279(4) 0.1238(19) Uani 1 1 d . . . . .
H24 H 0.1072 0.8148 -0.0909 0.149 Uiso 1 1 calc R U . . .
C25 C 0.1887(2) 0.7808(5) 0.0263(4) 0.1071(15) Uani 1 1 d . . . . .
H25 H 0.2122 0.8645 -0.0005 0.129 Uiso 1 1 calc R U . . .
N1 N 0.72979(13) 0.6763(3) 0.5250(3) 0.0682(8) Uani 1 1 d . . . . .
O1 O 0.66083(11) 0.6880(3) 0.4901(2) 0.0812(8) 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 1.373(6) . ?
C1 C6 1.385(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.456(4) . ?
C7 N1 1.279(4) . ?
C7 C8 1.490(4) . ?
C8 C9 1.512(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O1 1.474(3) . ?
C9 C10 1.513(4) . ?
C9 C11 1.514(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.479(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.202(4) . ?
C13 C14 1.437(5) . ?
C14 C19 1.372(4) . ?
C14 C15 1.382(4) . ?
C15 C16 1.383(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(4) . ?
C17 C20 1.480(4) . ?
C18 C19 1.379(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.356(5) . ?
C20 C21 1.368(5) . ?
C21 C22 1.378(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.327(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.350(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.367(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N1 O1 1.401(3) . ?

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 C6 121.3(4) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C1 C2 C3 119.5(5) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121.5(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 117.8(3) . . ?
C5 C6 C7 120.7(3) . . ?
C1 C6 C7 121.5(4) . . ?
N1 C7 C6 121.1(3) . . ?
N1 C7 C8 113.1(3) . . ?
C6 C7 C8 125.8(3) . . ?
C7 C8 C9 102.9(3) . . ?
C7 C8 H8A 111.2 . . ?
C9 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
O1 C9 C8 104.0(2) . . ?
O1 C9 C10 107.0(3) . . ?
C8 C9 C10 112.7(3) . . ?
O1 C9 C11 107.5(3) . . ?
C8 C9 C11 112.1(3) . . ?
C10 C9 C11 112.8(3) . . ?
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 . . ?
C12 C11 C9 114.0(3) . . ?
C12 C11 H11A 108.8 . . ?
C9 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C9 C11 H11B 108.8 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 177.0(4) . . ?
C12 C13 C14 175.0(4) . . ?
C19 C14 C15 117.6(3) . . ?
C19 C14 C13 121.2(3) . . ?
C15 C14 C13 121.2(3) . . ?
C14 C15 C16 121.7(3) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 115.8(3) . . ?
C18 C17 C20 121.2(3) . . ?
C16 C17 C20 122.9(3) . . ?
C19 C18 C17 122.9(3) . . ?
C19 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
C14 C19 C18 120.8(3) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C25 C20 C21 114.8(3) . . ?
C25 C20 C17 122.9(3) . . ?
C21 C20 C17 122.2(3) . . ?
C20 C21 C22 122.1(4) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C23 C22 C21 121.4(4) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C22 C23 C24 118.0(4) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C23 C24 C25 120.6(4) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 123.1(4) . . ?
C20 C25 H25 118.5 . . ?
C24 C25 H25 118.5 . . ?
C7 N1 O1 110.5(2) . . ?
N1 O1 C9 109.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(7) . . . . ?
C1 C2 C3 C4 0.0(8) . . . . ?
C2 C3 C4 C5 -0.3(8) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C4 C5 C6 C1 -1.0(6) . . . . ?
C4 C5 C6 C7 -179.5(4) . . . . ?
C2 C1 C6 C5 0.8(6) . . . . ?
C2 C1 C6 C7 179.3(4) . . . . ?
C5 C6 C7 N1 -168.7(3) . . . . ?
C1 C6 C7 N1 12.9(5) . . . . ?
C5 C6 C7 C8 10.8(5) . . . . ?
C1 C6 C7 C8 -167.6(3) . . . . ?
N1 C7 C8 C9 1.6(4) . . . . ?
C6 C7 C8 C9 -177.9(3) . . . . ?
C7 C8 C9 O1 -2.4(3) . . . . ?
C7 C8 C9 C10 113.1(3) . . . . ?
C7 C8 C9 C11 -118.3(3) . . . . ?
O1 C9 C11 C12 71.1(3) . . . . ?
C8 C9 C11 C12 -175.2(3) . . . . ?
C10 C9 C11 C12 -46.6(4) . . . . ?
C19 C14 C15 C16 -1.3(5) . . . . ?
C13 C14 C15 C16 175.7(3) . . . . ?
C14 C15 C16 C17 1.0(5) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C15 C16 C17 C20 -180.0(3) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C20 C17 C18 C19 179.8(3) . . . . ?
C15 C14 C19 C18 1.1(4) . . . . ?
C13 C14 C19 C18 -175.9(3) . . . . ?
C17 C18 C19 C14 -0.5(5) . . . . ?
C18 C17 C20 C25 -7.9(5) . . . . ?
C16 C17 C20 C25 171.7(3) . . . . ?
C18 C17 C20 C21 171.8(3) . . . . ?
C16 C17 C20 C21 -8.6(5) . . . . ?
C25 C20 C21 C22 -0.4(6) . . . . ?
C17 C20 C21 C22 180.0(4) . . . . ?
C20 C21 C22 C23 0.2(8) . . . . ?
C21 C22 C23 C24 0.6(8) . . . . ?
C22 C23 C24 C25 -1.3(8) . . . . ?
C21 C20 C25 C24 -0.3(6) . . . . ?
C17 C20 C25 C24 179.3(4) . . . . ?
C23 C24 C25 C20 1.2(8) . . . . ?
C6 C7 N1 O1 179.6(3) . . . . ?
C8 C7 N1 O1 0.1(4) . . . . ?
C7 N1 O1 C9 -1.8(4) . . . . ?
C8 C9 O1 N1 2.7(3) . . . . ?
C10 C9 O1 N1 -116.8(3) . . . . ?
C11 C9 O1 N1 121.7(3) . . . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_XSJ20231103_a
_database_code_depnum_ccdc_archive 'CCDC 2309690'
loop_
_audit_author_name
_audit_author_address
'Lei Wang'
;Yangzhou university
China
;
_audit_update_record             
;
2023-11-22 deposited with the CCDC.	2024-03-22 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         'C21 H21 N O2'
_chemical_formula_sum            'C21 H21 N O2'
_chemical_formula_weight         319.39

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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   20.0023(14)
_cell_length_b                   11.7633(14)
_cell_length_c                   31.100(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.763(4)
_cell_angle_gamma                90
_cell_volume                     6968.7(11)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             2720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6689
_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            47862
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.041
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_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 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             13434
_reflns_number_gt                7680
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.961
_reflns_Friedel_fraction_max     0.960
_reflns_Friedel_fraction_full    0.966

_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)+(0.0592P)²+1.1212P] 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_abs_structure_details 
;
 Flack x determined using 2757 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         13434
_refine_ls_number_parameters     873
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1406
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.2643(3) 0.8207(4) 0.34600(15) 0.0546(13) Uani 1 1 d . . . . .
H1 H 0.3058 0.7920 0.3655 0.066 Uiso 1 1 calc R U . . .
C2 C 0.2671(3) 0.8913(5) 0.31133(17) 0.0661(15) Uani 1 1 d . . . . .
H2 H 0.3102 0.9085 0.3074 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2072(4) 0.9361(5) 0.28275(17) 0.0683(16) Uani 1 1 d . . . . .
H3 H 0.2092 0.9832 0.2592 0.082 Uiso 1 1 calc R U . . .
C4 C 0.1439(3) 0.9113(5) 0.28888(17) 0.0754(17) Uani 1 1 d . . . . .
H4 H 0.1028 0.9423 0.2696 0.090 Uiso 1 1 calc R U . . .
C5 C 0.1408(3) 0.8403(4) 0.32370(16) 0.0611(14) Uani 1 1 d . . . . .
H5 H 0.0976 0.8250 0.3279 0.073 Uiso 1 1 calc R U . . .
C6 C 0.2012(2) 0.7913(4) 0.35253(14) 0.0430(11) Uani 1 1 d . . . . .
C7 C 0.1974(2) 0.7149(4) 0.38948(14) 0.0386(10) Uani 1 1 d . . . . .
C8 C 0.1315(2) 0.7076(4) 0.40192(16) 0.0529(13) Uani 1 1 d . . . . .
H8A H 0.0922 0.6965 0.3748 0.064 Uiso 1 1 calc R U . . .
H8B H 0.1242 0.7786 0.4157 0.064 Uiso 1 1 calc R U . . .
C9 C 0.1336(2) 0.6107(4) 0.43451(15) 0.0494(12) Uani 1 1 d . . . . .
H9A H 0.0993 0.6242 0.4503 0.059 Uiso 1 1 calc R U . . .
H9B H 0.1216 0.5400 0.4179 0.059 Uiso 1 1 calc R U . . .
C10 C 0.2058(2) 0.6012(4) 0.46819(14) 0.0415(11) Uani 1 1 d . . . . .
C11 C 0.2263(3) 0.7048(4) 0.49830(15) 0.0573(13) Uani 1 1 d . . . . .
H11A H 0.2723 0.6937 0.5192 0.086 Uiso 1 1 calc R U . . .
H11B H 0.1931 0.7156 0.5146 0.086 Uiso 1 1 calc R U . . .
H11C H 0.2265 0.7706 0.4801 0.086 Uiso 1 1 calc R U . . .
C12 C 0.2101(2) 0.4916(4) 0.49508(15) 0.0528(13) Uani 1 1 d . . . . .
H12A H 0.1733 0.4924 0.5094 0.063 Uiso 1 1 calc R U . . .
H12B H 0.2011 0.4280 0.4742 0.063 Uiso 1 1 calc R U . . .
C13 C 0.2777(3) 0.4723(4) 0.53006(16) 0.0516(12) Uani 1 1 d . . . . .
C14 C 0.3312(3) 0.4568(4) 0.55983(16) 0.0532(13) Uani 1 1 d . . . . .
C15 C 0.3940(2) 0.4375(4) 0.59641(14) 0.0473(12) Uani 1 1 d . . . . .
C16 C 0.4157(3) 0.3287(4) 0.61085(15) 0.0556(13) Uani 1 1 d . . . . .
H16 H 0.3897 0.2668 0.5962 0.067 Uiso 1 1 calc R U . . .
C17 C 0.4753(3) 0.3107(5) 0.64667(16) 0.0601(14) Uani 1 1 d . . . . .
H17 H 0.4889 0.2370 0.6563 0.072 Uiso 1 1 calc R U . . .
C18 C 0.5145(3) 0.4012(5) 0.66817(15) 0.0551(13) Uani 1 1 d . . . . .
C19 C 0.5993(3) 0.2792(6) 0.7179(2) 0.092(2) Uani 1 1 d . . . . .
H19A H 0.5663 0.2404 0.7295 0.138 Uiso 1 1 calc R U . . .
H19B H 0.6438 0.2838 0.7410 0.138 Uiso 1 1 calc R U . . .
H19C H 0.6047 0.2382 0.6925 0.138 Uiso 1 1 calc R U . . .
C20 C 0.4942(3) 0.5096(5) 0.65438(17) 0.0615(14) Uani 1 1 d . . . . .
H20 H 0.5206 0.5710 0.6692 0.074 Uiso 1 1 calc R U . . .
C21 C 0.4347(3) 0.5279(4) 0.61860(15) 0.0560(13) Uani 1 1 d . . . . .
H21 H 0.4215 0.6019 0.6092 0.067 Uiso 1 1 calc R U . . .
C22 C 0.1937(3) 0.3801(5) 0.34829(17) 0.0612(14) Uani 1 1 d . . . . .
H22 H 0.1690 0.4108 0.3665 0.073 Uiso 1 1 calc R U . . .
C23 C 0.2040(3) 0.4447(5) 0.31354(18) 0.0713(16) Uani 1 1 d . . . . .
H23 H 0.1855 0.5177 0.3082 0.086 Uiso 1 1 calc R U . . .
C24 C 0.2411(3) 0.4014(6) 0.28720(18) 0.0716(16) Uani 1 1 d . . . . .
H24 H 0.2475 0.4445 0.2637 0.086 Uiso 1 1 calc R U . . .
C25 C 0.2687(3) 0.2958(6) 0.29522(17) 0.0665(15) Uani 1 1 d . . . . .
H25 H 0.2948 0.2674 0.2775 0.080 Uiso 1 1 calc R U . . .
C26 C 0.2588(2) 0.2296(5) 0.32928(15) 0.0571(13) Uani 1 1 d . . . . .
H26 H 0.2783 0.1571 0.3343 0.068 Uiso 1 1 calc R U . . .
C27 C 0.2199(2) 0.2704(4) 0.35625(14) 0.0439(11) Uani 1 1 d . . . . .
C28 C 0.2079(2) 0.2003(4) 0.39263(14) 0.0412(11) Uani 1 1 d . . . . .
C29 C 0.2465(2) 0.0909(4) 0.40584(16) 0.0533(12) Uani 1 1 d . . . . .
H29A H 0.2960 0.1070 0.4195 0.064 Uiso 1 1 calc R U . . .
H29B H 0.2416 0.0459 0.3789 0.064 Uiso 1 1 calc R U . . .
C30 C 0.2201(2) 0.0222(4) 0.43873(14) 0.0488(12) Uani 1 1 d . . . . .
H30A H 0.1804 -0.0239 0.4221 0.059 Uiso 1 1 calc R U . . .
H30B H 0.2569 -0.0285 0.4558 0.059 Uiso 1 1 calc R U . . .
C31 C 0.1981(2) 0.0991(4) 0.47073(15) 0.0455(11) Uani 1 1 d . . . . .
C32 C 0.1585(3) 0.0361(5) 0.49773(18) 0.0701(15) Uani 1 1 d . . . . .
H32A H 0.1382 0.0898 0.5134 0.105 Uiso 1 1 calc R U . . .
H32B H 0.1903 -0.0128 0.5192 0.105 Uiso 1 1 calc R U . . .
H32C H 0.1220 -0.0087 0.4777 0.105 Uiso 1 1 calc R U . . .
C33 C 0.2589(3) 0.1676(4) 0.50151(15) 0.0549(13) Uani 1 1 d . . . . .
H33A H 0.2812 0.2102 0.4829 0.066 Uiso 1 1 calc R U . . .
H33B H 0.2402 0.2220 0.5183 0.066 Uiso 1 1 calc R U . . .
C34 C 0.3121(3) 0.0979(4) 0.53350(17) 0.0581(14) Uani 1 1 d . . . . .
C35 C 0.3545(3) 0.0444(5) 0.56119(16) 0.0567(13) Uani 1 1 d . . . . .
C36 C 0.4075(3) -0.0161(4) 0.59554(15) 0.0524(13) Uani 1 1 d . . . . .
C37 C 0.4767(3) 0.0167(4) 0.60808(15) 0.0580(13) Uani 1 1 d . . . . .
H37 H 0.4896 0.0788 0.5939 0.070 Uiso 1 1 calc R U . . .
C38 C 0.5277(3) -0.0405(4) 0.64144(17) 0.0592(14) Uani 1 1 d . . . . .
H38 H 0.5742 -0.0164 0.6496 0.071 Uiso 1 1 calc R U . . .
C39 C 0.5095(3) -0.1323(5) 0.66225(16) 0.0563(13) Uani 1 1 d . . . . .
C40 C 0.6273(3) -0.1610(6) 0.70992(19) 0.0855(19) Uani 1 1 d . . . . .
H40A H 0.6466 -0.1667 0.6852 0.128 Uiso 1 1 calc R U . . .
H40B H 0.6533 -0.2092 0.7342 0.128 Uiso 1 1 calc R U . . .
H40C H 0.6304 -0.0837 0.7202 0.128 Uiso 1 1 calc R U . . .
C41 C 0.4400(3) -0.1659(5) 0.65041(17) 0.0654(15) Uani 1 1 d . . . . .
H41 H 0.4273 -0.2272 0.6651 0.078 Uiso 1 1 calc R U . . .
C42 C 0.3898(3) -0.1101(5) 0.61737(17) 0.0662(15) Uani 1 1 d . . . . .
H42 H 0.3435 -0.1348 0.6093 0.079 Uiso 1 1 calc R U . . .
C43 C 0.5131(3) 0.5529(5) 0.34544(17) 0.0629(14) Uani 1 1 d . . . . .
H43 H 0.5535 0.5143 0.3617 0.076 Uiso 1 1 calc R U . . .
C44 C 0.5160(3) 0.6231(5) 0.31076(19) 0.0749(17) Uani 1 1 d . . . . .
H44 H 0.5578 0.6315 0.3038 0.090 Uiso 1 1 calc R U . . .
C45 C 0.4576(4) 0.6803(5) 0.28661(18) 0.0715(16) Uani 1 1 d . . . . .
H45 H 0.4592 0.7261 0.2626 0.086 Uiso 1 1 calc R U . . .
C46 C 0.3966(3) 0.6709(5) 0.29740(18) 0.0740(16) Uani 1 1 d . . . . .
H46 H 0.3571 0.7119 0.2813 0.089 Uiso 1 1 calc R U . . .
C47 C 0.3936(3) 0.5997(4) 0.33250(16) 0.0565(13) Uani 1 1 d . . . . .
H47 H 0.3519 0.5933 0.3397 0.068 Uiso 1 1 calc R U . . .
C48 C 0.4526(2) 0.5378(4) 0.35698(14) 0.0441(11) Uani 1 1 d . . . . .
C49 C 0.4493(2) 0.4616(4) 0.39411(14) 0.0418(11) Uani 1 1 d . . . . .
C50 C 0.3833(2) 0.4552(4) 0.40701(17) 0.0549(13) Uani 1 1 d . . . . .
H50A H 0.3438 0.4440 0.3801 0.066 Uiso 1 1 calc R U . . .
H50B H 0.3764 0.5266 0.4207 0.066 Uiso 1 1 calc R U . . .
C51 C 0.3859(2) 0.3590(4) 0.43984(16) 0.0548(13) Uani 1 1 d . . . . .
H51A H 0.3521 0.3729 0.4559 0.066 Uiso 1 1 calc R U . . .
H51B H 0.3735 0.2881 0.4234 0.066 Uiso 1 1 calc R U . . .
C52 C 0.4588(2) 0.3494(4) 0.47322(15) 0.0443(11) Uani 1 1 d . . . . .
C53 C 0.4797(3) 0.4535(4) 0.50227(16) 0.0608(14) Uani 1 1 d . . . . .
H53A H 0.5253 0.4422 0.5236 0.091 Uiso 1 1 calc R U . . .
H53B H 0.4461 0.4670 0.5181 0.091 Uiso 1 1 calc R U . . .
H53C H 0.4811 0.5179 0.4836 0.091 Uiso 1 1 calc R U . . .
C54 C 0.4649(3) 0.2409(4) 0.50068(17) 0.0609(14) Uani 1 1 d . . . . .
H54A H 0.4295 0.2426 0.5161 0.073 Uiso 1 1 calc R U . . .
H54B H 0.4545 0.1768 0.4801 0.073 Uiso 1 1 calc R U . . .
C55 C 0.5337(3) 0.2220(4) 0.53430(17) 0.0583(13) Uani 1 1 d . . . . .
C56 C 0.5874(3) 0.2055(5) 0.56304(17) 0.0578(14) Uani 1 1 d . . . . .
C57 C 0.6525(3) 0.1896(5) 0.59902(15) 0.0529(13) Uani 1 1 d . . . . .
C58 C 0.6807(3) 0.0831(4) 0.61072(17) 0.0611(14) Uani 1 1 d . . . . .
H58 H 0.6577 0.0199 0.5951 0.073 Uiso 1 1 calc R U . . .
C59 C 0.7429(3) 0.0685(5) 0.64550(16) 0.0646(15) Uani 1 1 d . . . . .
H59 H 0.7614 -0.0040 0.6529 0.077 Uiso 1 1 calc R U . . .
C60 C 0.7766(3) 0.1600(5) 0.66868(16) 0.0581(14) Uani 1 1 d . . . . .
C61 C 0.8681(3) 0.0466(6) 0.71737(19) 0.089(2) Uani 1 1 d . . . . .
H61A H 0.8366 0.0027 0.7286 0.133 Uiso 1 1 calc R U . . .
H61B H 0.9121 0.0551 0.7407 0.133 Uiso 1 1 calc R U . . .
H61C H 0.8757 0.0083 0.6920 0.133 Uiso 1 1 calc R U . . .
C62 C 0.7493(3) 0.2663(5) 0.65764(18) 0.0760(17) Uani 1 1 d . . . . .
H62 H 0.7722 0.3289 0.6738 0.091 Uiso 1 1 calc R U . . .
C63 C 0.6875(3) 0.2814(5) 0.62248(18) 0.0695(16) Uani 1 1 d . . . . .
H63 H 0.6699 0.3543 0.6148 0.083 Uiso 1 1 calc R U . . .
C64 C 0.5067(2) 0.9788(5) 0.32590(16) 0.0603(14) Uani 1 1 d . . . . .
H64 H 0.5261 0.9063 0.3308 0.072 Uiso 1 1 calc R U . . .
C65 C 0.5152(3) 1.0443(6) 0.29101(17) 0.0742(17) Uani 1 1 d . . . . .
H65 H 0.5396 1.0148 0.2724 0.089 Uiso 1 1 calc R U . . .
C66 C 0.4884(3) 1.1512(6) 0.28350(18) 0.0749(17) Uani 1 1 d . . . . .
H66 H 0.4945 1.1949 0.2601 0.090 Uiso 1 1 calc R U . . .
C67 C 0.4530(3) 1.1927(5) 0.3104(2) 0.0740(17) Uani 1 1 d . . . . .
H67 H 0.4343 1.2656 0.3051 0.089 Uiso 1 1 calc R U . . .
C68 C 0.4436(3) 1.1302(5) 0.34549(17) 0.0615(14) Uani 1 1 d . . . . .
H68 H 0.4196 1.1620 0.3639 0.074 Uiso 1 1 calc R U . . .
C69 C 0.4696(2) 1.0197(4) 0.35373(14) 0.0456(12) Uani 1 1 d . . . . .
C70 C 0.4580(2) 0.9511(4) 0.39069(14) 0.0409(11) Uani 1 1 d . . . . .
C71 C 0.4983(2) 0.8441(4) 0.40537(15) 0.0521(12) Uani 1 1 d . . . . .
H71A H 0.5473 0.8626 0.4197 0.063 Uiso 1 1 calc R U . . .
H71B H 0.4954 0.7979 0.3790 0.063 Uiso 1 1 calc R U . . .
C72 C 0.4715(2) 0.7762(4) 0.43780(14) 0.0445(11) Uani 1 1 d . . . . .
H72A H 0.4325 0.7290 0.4210 0.053 Uiso 1 1 calc R U . . .
H72B H 0.5085 0.7266 0.4554 0.053 Uiso 1 1 calc R U . . .
C73 C 0.4479(2) 0.8530(4) 0.46895(14) 0.0424(11) Uani 1 1 d . . . . .
C74 C 0.4084(3) 0.7895(4) 0.49614(16) 0.0599(14) Uani 1 1 d . . . . .
H74A H 0.3893 0.8430 0.5125 0.090 Uiso 1 1 calc R U . . .
H74B H 0.4400 0.7391 0.5170 0.090 Uiso 1 1 calc R U . . .
H74C H 0.3711 0.7463 0.4761 0.090 Uiso 1 1 calc R U . . .
C75 C 0.5082(2) 0.9243(4) 0.49976(15) 0.0500(12) Uani 1 1 d . . . . .
H75A H 0.5302 0.9671 0.4811 0.060 Uiso 1 1 calc R U . . .
H75B H 0.4887 0.9785 0.5162 0.060 Uiso 1 1 calc R U . . .
C76 C 0.5618(3) 0.8567(4) 0.53209(16) 0.0517(12) Uani 1 1 d . . . . .
C77 C 0.6038(3) 0.8022(4) 0.55991(16) 0.0526(13) Uani 1 1 d . . . . .
C78 C 0.6517(3) 0.7369(4) 0.59488(14) 0.0459(11) Uani 1 1 d . . . . .
C79 C 0.6268(3) 0.6490(5) 0.61529(16) 0.0594(14) Uani 1 1 d . . . . .
H79 H 0.5791 0.6326 0.6058 0.071 Uiso 1 1 calc R U . . .
C80 C 0.6710(3) 0.5855(4) 0.64917(17) 0.0627(14) Uani 1 1 d . . . . .
H80 H 0.6533 0.5269 0.6626 0.075 Uiso 1 1 calc R U . . .
C81 C 0.7421(3) 0.6096(4) 0.66316(16) 0.0541(13) Uani 1 1 d . . . . .
C82 C 0.8552(3) 0.5586(6) 0.7128(2) 0.092(2) Uani 1 1 d . . . . .
H82A H 0.8744 0.5521 0.6881 0.138 Uiso 1 1 calc R U . . .
H82B H 0.8765 0.5027 0.7353 0.138 Uiso 1 1 calc R U . . .
H82C H 0.8647 0.6332 0.7258 0.138 Uiso 1 1 calc R U . . .
C83 C 0.7679(3) 0.6962(5) 0.64367(17) 0.0598(14) Uani 1 1 d . . . . .
H83 H 0.8156 0.7126 0.6534 0.072 Uiso 1 1 calc R U . . .
C84 C 0.7229(3) 0.7593(4) 0.60955(16) 0.0574(13) Uani 1 1 d . . . . .
H84 H 0.7408 0.8179 0.5962 0.069 Uiso 1 1 calc R U . . .
N1 N 0.25422(18) 0.6590(3) 0.40804(11) 0.0440(9) Uani 1 1 d . . . . .
N2 N 0.1625(2) 0.2413(3) 0.40994(13) 0.0533(10) Uani 1 1 d . . . . .
N3 N 0.50550(19) 0.4054(3) 0.41196(12) 0.0474(10) Uani 1 1 d . . . . .
N4 N 0.41163(18) 0.9915(3) 0.40726(12) 0.0484(10) Uani 1 1 d . . . . .
O1 O 0.25662(14) 0.5842(3) 0.44398(9) 0.0451(8) Uani 1 1 d . . . . .
O2 O 0.57433(19) 0.3910(4) 0.70411(12) 0.0808(12) Uani 1 1 d . . . . .
O3 O 0.14730(16) 0.1816(3) 0.44489(11) 0.0596(9) Uani 1 1 d . . . . .
O4 O 0.5560(2) -0.1955(3) 0.69532(12) 0.0772(11) Uani 1 1 d . . . . .
O5 O 0.50910(15) 0.3318(3) 0.44822(10) 0.0489(8) Uani 1 1 d . . . . .
O6 O 0.8386(2) 0.1553(4) 0.70376(12) 0.0819(12) Uani 1 1 d . . . . .
O7 O 0.39678(16) 0.9337(3) 0.44245(10) 0.0553(9) Uani 1 1 d . . . . .
O8 O 0.7818(2) 0.5406(3) 0.69692(12) 0.0776(11) 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 1.376(7) . ?
C1 C6 1.382(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.479(6) . ?
C7 N1 1.287(5) . ?
C7 C8 1.486(6) . ?
C8 C9 1.517(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.507(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O1 1.452(5) . ?
C10 C11 1.515(6) . ?
C10 C12 1.526(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.471(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.196(6) . ?
C14 C15 1.433(7) . ?
C15 C16 1.382(7) . ?
C15 C21 1.388(6) . ?
C16 C17 1.377(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(7) . ?
C17 H17 0.9300 . ?
C18 C20 1.367(7) . ?
C18 O2 1.371(6) . ?
C19 O2 1.425(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.376(7) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.386(7) . ?
C22 C23 1.387(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.362(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.351(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.393(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.477(6) . ?
C28 N2 1.282(5) . ?
C28 C29 1.492(6) . ?
C29 C30 1.520(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.506(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 O3 1.457(5) . ?
C31 C32 1.512(6) . ?
C31 C33 1.527(6) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.465(7) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.189(7) . ?
C35 C36 1.442(7) . ?
C36 C37 1.373(7) . ?
C36 C42 1.399(7) . ?
C37 C38 1.387(7) . ?
C37 H37 0.9300 . ?
C38 C39 1.365(7) . ?
C38 H38 0.9300 . ?
C39 O4 1.376(6) . ?
C39 C41 1.382(7) . ?
C40 O4 1.418(7) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.366(7) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C43 C44 1.374(7) . ?
C43 C48 1.376(6) . ?
C43 H43 0.9300 . ?
C44 C45 1.358(8) . ?
C44 H44 0.9300 . ?
C45 C46 1.366(8) . ?
C45 H45 0.9300 . ?
C46 C47 1.392(7) . ?
C46 H46 0.9300 . ?
C47 C48 1.398(6) . ?
C47 H47 0.9300 . ?
C48 C49 1.479(6) . ?
C49 N3 1.277(5) . ?
C49 C50 1.493(6) . ?
C50 C51 1.515(7) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C51 C52 1.515(6) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 O5 1.461(5) . ?
C52 C53 1.504(6) . ?
C52 C54 1.519(6) . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C54 C55 1.470(7) . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C55 C56 1.184(6) . ?
C56 C57 1.448(7) . ?
C57 C63 1.371(7) . ?
C57 C58 1.376(7) . ?
C58 C59 1.387(7) . ?
C58 H58 0.9300 . ?
C59 C60 1.355(7) . ?
C59 H59 0.9300 . ?
C60 C62 1.366(7) . ?
C60 O6 1.379(6) . ?
C61 O6 1.419(7) . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
C62 C63 1.389(7) . ?
C62 H62 0.9300 . ?
C63 H63 0.9300 . ?
C64 C65 1.383(7) . ?
C64 C69 1.386(6) . ?
C64 H64 0.9300 . ?
C65 C66 1.359(8) . ?
C65 H65 0.9300 . ?
C66 C67 1.341(8) . ?
C66 H66 0.9300 . ?
C67 C68 1.377(7) . ?
C67 H67 0.9300 . ?
C68 C69 1.394(7) . ?
C68 H68 0.9300 . ?
C69 C70 1.479(6) . ?
C70 N4 1.283(5) . ?
C70 C71 1.489(6) . ?
C71 C72 1.507(6) . ?
C71 H71A 0.9700 . ?
C71 H71B 0.9700 . ?
C72 C73 1.503(6) . ?
C72 H72A 0.9700 . ?
C72 H72B 0.9700 . ?
C73 O7 1.453(5) . ?
C73 C74 1.517(6) . ?
C73 C75 1.540(6) . ?
C74 H74A 0.9600 . ?
C74 H74B 0.9600 . ?
C74 H74C 0.9600 . ?
C75 C76 1.461(7) . ?
C75 H75A 0.9700 . ?
C75 H75B 0.9700 . ?
C76 C77 1.193(6) . ?
C77 C78 1.434(7) . ?
C78 C79 1.382(6) . ?
C78 C84 1.383(6) . ?
C79 C80 1.371(7) . ?
C79 H79 0.9300 . ?
C80 C81 1.385(7) . ?
C80 H80 0.9300 . ?
C81 C83 1.364(7) . ?
C81 O8 1.372(6) . ?
C82 O8 1.416(7) . ?
C82 H82A 0.9600 . ?
C82 H82B 0.9600 . ?
C82 H82C 0.9600 . ?
C83 C84 1.380(7) . ?
C83 H83 0.9300 . ?
C84 H84 0.9300 . ?
N1 O1 1.411(4) . ?
N2 O3 1.403(5) . ?
N3 O5 1.406(4) . ?
N4 O7 1.395(5) . ?

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 C6 121.6(5) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C3 C2 C1 120.4(5) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.6(5) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.1(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 117.0(4) . . ?
C1 C6 C7 122.1(4) . . ?
C5 C6 C7 120.9(4) . . ?
N1 C7 C6 114.4(4) . . ?
N1 C7 C8 125.9(4) . . ?
C6 C7 C8 119.8(4) . . ?
C7 C8 C9 111.8(4) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 110.2(4) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O1 C10 C9 108.9(3) . . ?
O1 C10 C11 109.3(3) . . ?
C9 C10 C11 113.0(4) . . ?
O1 C10 C12 103.6(4) . . ?
C9 C10 C12 109.0(3) . . ?
C11 C10 C12 112.4(3) . . ?
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 115.0(4) . . ?
C13 C12 H12A 108.5 . . ?
C10 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C10 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C12 177.3(5) . . ?
C13 C14 C15 178.2(5) . . ?
C16 C15 C21 118.0(4) . . ?
C16 C15 C14 121.1(5) . . ?
C21 C15 C14 120.8(5) . . ?
C17 C16 C15 120.9(5) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.0(5) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C20 C18 C17 120.1(5) . . ?
C20 C18 O2 116.0(5) . . ?
C17 C18 O2 123.9(5) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 C21 120.1(5) . . ?
C18 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C15 120.8(5) . . ?
C20 C21 H21 119.6 . . ?
C15 C21 H21 119.6 . . ?
C27 C22 C23 120.8(5) . . ?
C27 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 120.1(6) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 120.0(5) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 121.0(5) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C27 120.4(5) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 117.6(4) . . ?
C22 C27 C28 121.1(4) . . ?
C26 C27 C28 121.4(4) . . ?
N2 C28 C27 114.4(4) . . ?
N2 C28 C29 125.6(4) . . ?
C27 C28 C29 120.0(4) . . ?
C28 C29 C30 112.8(4) . . ?
C28 C29 H29A 109.0 . . ?
C30 C29 H29A 109.0 . . ?
C28 C29 H29B 109.0 . . ?
C30 C29 H29B 109.0 . . ?
H29A C29 H29B 107.8 . . ?
C31 C30 C29 110.8(4) . . ?
C31 C30 H30A 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 108.1 . . ?
O3 C31 C30 109.3(4) . . ?
O3 C31 C32 103.7(4) . . ?
C30 C31 C32 112.3(4) . . ?
O3 C31 C33 106.4(4) . . ?
C30 C31 C33 113.3(4) . . ?
C32 C31 C33 111.2(4) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C31 113.8(4) . . ?
C34 C33 H33A 108.8 . . ?
C31 C33 H33A 108.8 . . ?
C34 C33 H33B 108.8 . . ?
C31 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C35 C34 C33 176.6(5) . . ?
C34 C35 C36 177.5(6) . . ?
C37 C36 C42 117.8(5) . . ?
C37 C36 C35 121.4(5) . . ?
C42 C36 C35 120.7(5) . . ?
C36 C37 C38 121.6(5) . . ?
C36 C37 H37 119.2 . . ?
C38 C37 H37 119.2 . . ?
C39 C38 C37 119.8(5) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C38 C39 O4 124.4(5) . . ?
C38 C39 C41 119.5(5) . . ?
O4 C39 C41 116.2(5) . . ?
O4 C40 H40A 109.5 . . ?
O4 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O4 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 C39 120.8(5) . . ?
C42 C41 H41 119.6 . . ?
C39 C41 H41 119.6 . . ?
C41 C42 C36 120.5(5) . . ?
C41 C42 H42 119.7 . . ?
C36 C42 H42 119.7 . . ?
C44 C43 C48 122.3(5) . . ?
C44 C43 H43 118.8 . . ?
C48 C43 H43 118.8 . . ?
C45 C44 C43 119.7(5) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C44 C45 C46 120.4(5) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C45 C46 C47 119.8(5) . . ?
C45 C46 H46 120.1 . . ?
C47 C46 H46 120.1 . . ?
C46 C47 C48 120.6(5) . . ?
C46 C47 H47 119.7 . . ?
C48 C47 H47 119.7 . . ?
C43 C48 C47 117.0(4) . . ?
C43 C48 C49 122.3(4) . . ?
C47 C48 C49 120.7(4) . . ?
N3 C49 C48 114.2(4) . . ?
N3 C49 C50 126.2(4) . . ?
C48 C49 C50 119.6(4) . . ?
C49 C50 C51 111.6(4) . . ?
C49 C50 H50A 109.3 . . ?
C51 C50 H50A 109.3 . . ?
C49 C50 H50B 109.3 . . ?
C51 C50 H50B 109.3 . . ?
H50A C50 H50B 108.0 . . ?
C52 C51 C50 110.2(4) . . ?
C52 C51 H51A 109.6 . . ?
C50 C51 H51A 109.6 . . ?
C52 C51 H51B 109.6 . . ?
C50 C51 H51B 109.6 . . ?
H51A C51 H51B 108.1 . . ?
O5 C52 C53 109.0(3) . . ?
O5 C52 C51 108.7(3) . . ?
C53 C52 C51 112.6(4) . . ?
O5 C52 C54 103.3(4) . . ?
C53 C52 C54 112.7(4) . . ?
C51 C52 C54 110.0(4) . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C55 C54 C52 115.1(4) . . ?
C55 C54 H54A 108.5 . . ?
C52 C54 H54A 108.5 . . ?
C55 C54 H54B 108.5 . . ?
C52 C54 H54B 108.5 . . ?
H54A C54 H54B 107.5 . . ?
C56 C55 C54 176.5(5) . . ?
C55 C56 C57 177.7(6) . . ?
C63 C57 C58 118.4(5) . . ?
C63 C57 C56 120.2(5) . . ?
C58 C57 C56 121.5(5) . . ?
C57 C58 C59 121.1(5) . . ?
C57 C58 H58 119.5 . . ?
C59 C58 H58 119.5 . . ?
C60 C59 C58 120.0(5) . . ?
C60 C59 H59 120.0 . . ?
C58 C59 H59 120.0 . . ?
C59 C60 C62 119.8(5) . . ?
C59 C60 O6 124.8(5) . . ?
C62 C60 O6 115.4(5) . . ?
O6 C61 H61A 109.5 . . ?
O6 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
O6 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C60 C62 C63 120.5(5) . . ?
C60 C62 H62 119.8 . . ?
C63 C62 H62 119.8 . . ?
C57 C63 C62 120.3(5) . . ?
C57 C63 H63 119.8 . . ?
C62 C63 H63 119.8 . . ?
C65 C64 C69 120.9(5) . . ?
C65 C64 H64 119.6 . . ?
C69 C64 H64 119.6 . . ?
C66 C65 C64 120.9(6) . . ?
C66 C65 H65 119.5 . . ?
C64 C65 H65 119.5 . . ?
C67 C66 C65 119.1(6) . . ?
C67 C66 H66 120.5 . . ?
C65 C66 H66 120.5 . . ?
C66 C67 C68 121.7(6) . . ?
C66 C67 H67 119.1 . . ?
C68 C67 H67 119.1 . . ?
C67 C68 C69 120.6(5) . . ?
C67 C68 H68 119.7 . . ?
C69 C68 H68 119.7 . . ?
C64 C69 C68 116.7(4) . . ?
C64 C69 C70 122.4(4) . . ?
C68 C69 C70 120.9(4) . . ?
N4 C70 C69 114.4(4) . . ?
N4 C70 C71 125.5(4) . . ?
C69 C70 C71 120.1(4) . . ?
C70 C71 C72 112.6(4) . . ?
C70 C71 H71A 109.1 . . ?
C72 C71 H71A 109.1 . . ?
C70 C71 H71B 109.1 . . ?
C72 C71 H71B 109.1 . . ?
H71A C71 H71B 107.8 . . ?
C73 C72 C71 111.0(4) . . ?
C73 C72 H72A 109.4 . . ?
C71 C72 H72A 109.4 . . ?
C73 C72 H72B 109.4 . . ?
C71 C72 H72B 109.4 . . ?
H72A C72 H72B 108.0 . . ?
O7 C73 C72 109.4(3) . . ?
O7 C73 C74 104.1(4) . . ?
C72 C73 C74 112.5(4) . . ?
O7 C73 C75 106.2(4) . . ?
C72 C73 C75 112.8(4) . . ?
C74 C73 C75 111.3(4) . . ?
C73 C74 H74A 109.5 . . ?
C73 C74 H74B 109.5 . . ?
H74A C74 H74B 109.5 . . ?
C73 C74 H74C 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
C76 C75 C73 113.7(4) . . ?
C76 C75 H75A 108.8 . . ?
C73 C75 H75A 108.8 . . ?
C76 C75 H75B 108.8 . . ?
C73 C75 H75B 108.8 . . ?
H75A C75 H75B 107.7 . . ?
C77 C76 C75 176.9(5) . . ?
C76 C77 C78 176.8(5) . . ?
C79 C78 C84 118.1(4) . . ?
C79 C78 C77 119.9(5) . . ?
C84 C78 C77 122.0(5) . . ?
C80 C79 C78 121.5(5) . . ?
C80 C79 H79 119.2 . . ?
C78 C79 H79 119.2 . . ?
C79 C80 C81 119.3(5) . . ?
C79 C80 H80 120.4 . . ?
C81 C80 H80 120.4 . . ?
C83 C81 O8 124.9(5) . . ?
C83 C81 C80 120.3(5) . . ?
O8 C81 C80 114.7(5) . . ?
O8 C82 H82A 109.5 . . ?
O8 C82 H82B 109.5 . . ?
H82A C82 H82B 109.5 . . ?
O8 C82 H82C 109.5 . . ?
H82A C82 H82C 109.5 . . ?
H82B C82 H82C 109.5 . . ?
C81 C83 C84 119.9(5) . . ?
C81 C83 H83 120.1 . . ?
C84 C83 H83 120.1 . . ?
C83 C84 C78 121.0(5) . . ?
C83 C84 H84 119.5 . . ?
C78 C84 H84 119.5 . . ?
C7 N1 O1 119.1(3) . . ?
C28 N2 O3 119.0(4) . . ?
C49 N3 O5 119.4(3) . . ?
C70 N4 O7 119.2(4) . . ?
N1 O1 C10 117.7(3) . . ?
C18 O2 C19 117.7(5) . . ?
N2 O3 C31 118.8(3) . . ?
C39 O4 C40 118.0(5) . . ?
N3 O5 C52 117.7(3) . . ?
C60 O6 C61 117.6(5) . . ?
N4 O7 C73 118.9(3) . . ?
C81 O8 C82 118.4(5) . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036

