# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_HL3
_database_code_depnum_ccdc_archive 'CCDC 1533444'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-12-19 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         'C15 H13 N O2'
_chemical_formula_sum            'C15 H13 N O2'
_chemical_formula_weight         239.26

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                   24.5835(17)
_cell_length_b                   7.2032(5)
_cell_length_c                   14.2362(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.711(7)
_cell_angle_gamma                90
_cell_volume                     2426.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1936
_cell_measurement_theta_max      28.2490
_cell_measurement_theta_min      3.8090

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11916
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.202
_diffrn_reflns_theta_max         28.859
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5568
_reflns_number_gt                2802
_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_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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)+(0.0664P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5568
_refine_ls_number_parameters     331
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1679
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_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 0.88343(10) 0.3172(3) 0.49558(17) 0.0423(6) Uani 1 1 d . . . . .
C2 C 0.83764(9) 0.2944(3) 0.54355(16) 0.0380(5) Uani 1 1 d . . . . .
C3 C 0.84840(10) 0.2075(3) 0.63286(17) 0.0463(6) Uani 1 1 d . . . . .
H3 H 0.8842 0.1598 0.6619 0.056 Uiso 1 1 calc R U . . .
C4 C 0.80609(10) 0.1912(3) 0.67911(17) 0.0488(6) Uani 1 1 d . . . . .
H4 H 0.8136 0.1324 0.7394 0.059 Uiso 1 1 calc R U . . .
C5 C 0.75272(9) 0.2610(3) 0.63728(16) 0.0409(5) Uani 1 1 d . . . . .
C6 C 0.74199(10) 0.3472(3) 0.54644(17) 0.0468(6) Uani 1 1 d . . . . .
H6 H 0.7061 0.3930 0.5166 0.056 Uiso 1 1 calc R U . . .
C7 C 0.78429(10) 0.3648(3) 0.50091(17) 0.0453(6) Uani 1 1 d . . . . .
H7 H 0.7770 0.4246 0.4409 0.054 Uiso 1 1 calc R U . . .
N1 N 0.65751(8) 0.2732(3) 0.65073(14) 0.0487(5) Uani 1 1 d . . . . .
C9 C 0.61915(10) 0.2518(3) 0.70916(18) 0.0448(6) Uani 1 1 d . . . . .
C10 C 0.63166(10) 0.2999(3) 0.80646(18) 0.0513(6) Uani 1 1 d . . . . .
H10 H 0.6668 0.3501 0.8372 0.062 Uiso 1 1 calc R U . . .
C11 C 0.59239(11) 0.2740(3) 0.85855(19) 0.0540(7) Uani 1 1 d . . . . .
H11 H 0.6015 0.3077 0.9240 0.065 Uiso 1 1 calc R U . . .
C12 C 0.54001(10) 0.1995(3) 0.81581(19) 0.0477(6) Uani 1 1 d . . . . .
C13 C 0.52764(10) 0.1543(3) 0.7187(2) 0.0543(7) Uani 1 1 d . . . . .
H13 H 0.4923 0.1049 0.6881 0.065 Uiso 1 1 calc R U . . .
C14 C 0.56639(10) 0.1804(3) 0.66497(18) 0.0508(6) Uani 1 1 d . . . . .
H14 H 0.5568 0.1498 0.5991 0.061 Uiso 1 1 calc R U . . .
C15 C 0.49726(12) 0.1695(4) 0.8725(2) 0.0685(8) Uani 1 1 d . . . . .
H15A H 0.5129 0.2085 0.9388 0.103 Uiso 1 1 calc R U . . .
H15B H 0.4639 0.2408 0.8436 0.103 Uiso 1 1 calc R U . . .
H15C H 0.4876 0.0402 0.8712 0.103 Uiso 1 1 calc R U . . .
C21 C 0.99691(10) 0.6430(3) 0.62889(17) 0.0420(6) Uani 1 1 d . . . . .
C22 C 0.95292(9) 0.6433(3) 0.68137(16) 0.0382(5) Uani 1 1 d . . . . .
C23 C 0.96489(9) 0.5828(3) 0.77631(16) 0.0453(6) Uani 1 1 d . . . . .
H23 H 1.0010 0.5404 0.8076 0.054 Uiso 1 1 calc R U . . .
C24 C 0.92374(10) 0.5848(3) 0.82528(17) 0.0505(6) Uani 1 1 d . . . . .
H24 H 0.9324 0.5447 0.8897 0.061 Uiso 1 1 calc R U . . .
C25 C 0.86941(9) 0.6460(3) 0.77944(16) 0.0398(5) Uani 1 1 d . . . . .
C26 C 0.85787(10) 0.7068(3) 0.68420(17) 0.0462(6) Uani 1 1 d . . . . .
H26 H 0.8218 0.7487 0.6526 0.055 Uiso 1 1 calc R U . . .
C27 C 0.89916(10) 0.7063(3) 0.63547(17) 0.0477(6) Uani 1 1 d . . . . .
H27 H 0.8909 0.7484 0.5714 0.057 Uiso 1 1 calc R U . . .
C28 C 0.82657(10) 0.6475(3) 0.83267(17) 0.0495(6) Uani 1 1 d . . . . .
H28 H 0.8366 0.6062 0.8970 0.059 Uiso 1 1 calc R U . . .
C29 C 0.73680(9) 0.7054(3) 0.85139(16) 0.0390(5) Uani 1 1 d . . . . .
C30 C 0.74591(10) 0.6422(3) 0.94641(17) 0.0479(6) Uani 1 1 d . . . . .
H30 H 0.7802 0.5869 0.9780 0.057 Uiso 1 1 calc R U . . .
C31 C 0.70446(10) 0.6610(3) 0.99393(17) 0.0501(6) Uani 1 1 d . . . . .
H31 H 0.7112 0.6178 1.0576 0.060 Uiso 1 1 calc R U . . .
C32 C 0.65309(10) 0.7421(3) 0.94988(18) 0.0454(6) Uani 1 1 d . . . . .
C33 C 0.64408(10) 0.8015(3) 0.85485(18) 0.0512(6) Uani 1 1 d . . . . .
H33 H 0.6095 0.8546 0.8228 0.061 Uiso 1 1 calc R U . . .
C34 C 0.68537(10) 0.7837(3) 0.80647(17) 0.0472(6) Uani 1 1 d . . . . .
H34 H 0.6783 0.8253 0.7425 0.057 Uiso 1 1 calc R U . . .
C35 C 0.60890(11) 0.7664(4) 1.0045(2) 0.0672(8) Uani 1 1 d . . . . .
H35A H 0.5761 0.8248 0.9627 0.101 Uiso 1 1 calc R U . . .
H35B H 0.5987 0.6471 1.0246 0.101 Uiso 1 1 calc R U . . .
H35C H 0.6238 0.8426 1.0609 0.101 Uiso 1 1 calc R U . . .
C8 C 0.70906(10) 0.2398(3) 0.68846(17) 0.0471(6) Uani 1 1 d . . . . .
H8 H 0.7200 0.1991 0.7529 0.057 Uiso 1 1 calc R U . . .
N2 N 0.77726(8) 0.7012(3) 0.79659(14) 0.0488(5) Uani 1 1 d . . . . .
O1 O 0.93069(7) 0.2431(3) 0.53553(13) 0.0621(5) Uani 1 1 d D . . . .
O2 O 0.87455(7) 0.4101(2) 0.41770(12) 0.0612(5) Uani 1 1 d . . . . .
O3 O 0.98608(7) 0.7146(3) 0.54479(12) 0.0620(5) Uani 1 1 d . . . . .
O4 O 1.04427(7) 0.5730(2) 0.67084(12) 0.0581(5) Uani 1 1 d D . . . .
H1O H 0.9611(10) 0.268(4) 0.5074(19) 0.087 Uiso 1 1 d D U . . .
H4O H 1.0714(10) 0.585(4) 0.6377(18) 0.087 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.263(3) . ?
C1 O1 1.265(3) . ?
C1 C2 1.475(3) . ?
C2 C3 1.377(3) . ?
C2 C7 1.384(3) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 C8 1.459(3) . ?
C6 C7 1.372(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
N1 C8 1.259(3) . ?
N1 C9 1.425(3) . ?
C9 C14 1.378(3) . ?
C9 C10 1.379(3) . ?
C10 C11 1.380(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(3) . ?
C12 C15 1.504(3) . ?
C13 C14 1.386(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C21 O4 1.261(3) . ?
C21 O3 1.264(3) . ?
C21 C22 1.471(3) . ?
C22 C23 1.374(3) . ?
C22 C27 1.383(3) . ?
C23 C24 1.375(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.390(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.379(3) . ?
C25 C28 1.454(3) . ?
C26 C27 1.376(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 N2 1.243(3) . ?
C28 H28 0.9300 . ?
C29 C34 1.374(3) . ?
C29 C30 1.387(3) . ?
C29 N2 1.421(3) . ?
C30 C31 1.374(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.378(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.379(3) . ?
C32 C35 1.507(3) . ?
C33 C34 1.378(3) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C8 H8 0.9300 . ?
O1 H1O 0.956(17) . ?
O4 H4O 0.920(17) . ?

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
O2 C1 O1 122.5(2) . . ?
O2 C1 C2 119.6(2) . . ?
O1 C1 C2 117.9(2) . . ?
C3 C2 C7 119.6(2) . . ?
C3 C2 C1 119.9(2) . . ?
C7 C2 C1 120.5(2) . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 C8 119.2(2) . . ?
C6 C5 C8 122.0(2) . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C8 N1 C9 118.6(2) . . ?
C14 C9 C10 118.6(2) . . ?
C14 C9 N1 117.6(2) . . ?
C10 C9 N1 123.8(2) . . ?
C9 C10 C11 120.5(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 117.6(2) . . ?
C13 C12 C15 120.7(2) . . ?
C11 C12 C15 121.7(2) . . ?
C12 C13 C14 121.7(2) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C9 C14 C13 120.1(2) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C21 O3 122.9(2) . . ?
O4 C21 C22 118.1(2) . . ?
O3 C21 C22 119.0(2) . . ?
C23 C22 C27 119.4(2) . . ?
C23 C22 C21 120.5(2) . . ?
C27 C22 C21 120.0(2) . . ?
C22 C23 C24 120.3(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C25 120.7(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 118.5(2) . . ?
C26 C25 C28 121.6(2) . . ?
C24 C25 C28 119.8(2) . . ?
C27 C26 C25 120.8(2) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C22 120.3(2) . . ?
C26 C27 H27 119.9 . . ?
C22 C27 H27 119.9 . . ?
N2 C28 C25 123.3(2) . . ?
N2 C28 H28 118.3 . . ?
C25 C28 H28 118.3 . . ?
C34 C29 C30 118.3(2) . . ?
C34 C29 N2 116.5(2) . . ?
C30 C29 N2 125.2(2) . . ?
C31 C30 C29 120.2(2) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 121.9(2) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C31 C32 C33 117.5(2) . . ?
C31 C32 C35 120.9(2) . . ?
C33 C32 C35 121.5(2) . . ?
C34 C33 C32 121.1(2) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C29 C34 C33 121.0(2) . . ?
C29 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N1 C8 C5 124.0(2) . . ?
N1 C8 H8 118.0 . . ?
C5 C8 H8 118.0 . . ?
C28 N2 C29 121.9(2) . . ?
C1 O1 H1O 117.4(17) . . ?
C21 O4 H4O 115.1(17) . . ?

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
O2 C1 C2 C3 -174.2(2) . . . . ?
O1 C1 C2 C3 5.0(3) . . . . ?
O2 C1 C2 C7 3.8(3) . . . . ?
O1 C1 C2 C7 -176.9(2) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C4 178.0(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C8 179.6(2) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
C8 C5 C6 C7 179.8(2) . . . . ?
C5 C6 C7 C2 1.2(3) . . . . ?
C3 C2 C7 C6 -0.6(3) . . . . ?
C1 C2 C7 C6 -178.6(2) . . . . ?
C8 N1 C9 C14 -142.3(2) . . . . ?
C8 N1 C9 C10 38.3(3) . . . . ?
C14 C9 C10 C11 1.1(4) . . . . ?
N1 C9 C10 C11 -179.6(2) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C13 -1.1(4) . . . . ?
C10 C11 C12 C15 179.5(2) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C15 C12 C13 C14 -179.9(2) . . . . ?
C10 C9 C14 C13 -1.5(3) . . . . ?
N1 C9 C14 C13 179.2(2) . . . . ?
C12 C13 C14 C9 0.7(4) . . . . ?
O4 C21 C22 C23 5.3(3) . . . . ?
O3 C21 C22 C23 -173.8(2) . . . . ?
O4 C21 C22 C27 -175.3(2) . . . . ?
O3 C21 C22 C27 5.6(3) . . . . ?
C27 C22 C23 C24 0.1(3) . . . . ?
C21 C22 C23 C24 179.5(2) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C23 C24 C25 C26 -0.8(3) . . . . ?
C23 C24 C25 C28 -179.8(2) . . . . ?
C24 C25 C26 C27 0.3(3) . . . . ?
C28 C25 C26 C27 179.2(2) . . . . ?
C25 C26 C27 C22 0.4(3) . . . . ?
C23 C22 C27 C26 -0.6(3) . . . . ?
C21 C22 C27 C26 -180.0(2) . . . . ?
C26 C25 C28 N2 0.7(4) . . . . ?
C24 C25 C28 N2 179.6(2) . . . . ?
C34 C29 C30 C31 -1.0(3) . . . . ?
N2 C29 C30 C31 177.0(2) . . . . ?
C29 C30 C31 C32 0.0(4) . . . . ?
C30 C31 C32 C33 1.1(4) . . . . ?
C30 C31 C32 C35 -178.2(2) . . . . ?
C31 C32 C33 C34 -1.2(3) . . . . ?
C35 C32 C33 C34 178.1(2) . . . . ?
C30 C29 C34 C33 0.9(3) . . . . ?
N2 C29 C34 C33 -177.3(2) . . . . ?
C32 C33 C34 C29 0.2(4) . . . . ?
C9 N1 C8 C5 -178.4(2) . . . . ?
C4 C5 C8 N1 -169.0(2) . . . . ?
C6 C5 C8 N1 9.9(4) . . . . ?
C25 C28 N2 C29 -178.37(19) . . . . ?
C34 C29 N2 C28 174.1(2) . . . . ?
C30 C29 N2 C28 -4.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O3 0.956(17) 1.666(17) 2.618(2) 173(3) 3_766
O4 H4O O2 0.920(17) 1.719(17) 2.636(2) 175(3) 3_766

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_HL6
_database_code_depnum_ccdc_archive 'CCDC 1533446'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-12-19 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         'C16 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   4.8722(6)
_cell_length_b                   7.6353(8)
_cell_length_c                   19.256(2)
_cell_angle_alpha                92.857(9)
_cell_angle_beta                 96.511(9)
_cell_angle_gamma                104.261(10)
_cell_volume                     687.53(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    767
_cell_measurement_theta_max      24.5840
_cell_measurement_theta_min      3.6220

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5200
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.353
_diffrn_reflns_theta_max         28.663
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3103
_reflns_number_gt                1618
_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_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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)+(0.1006P)²+0.4580P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3103
_refine_ls_number_parameters     184
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_gt           0.0857
_refine_ls_wR_factor_ref         0.2578
_refine_ls_wR_factor_gt          0.2099
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_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 0.8007(7) 0.1416(4) 0.55094(17) 0.0409(8) Uani 1 1 d . . . . .
C2 C 0.6577(7) 0.2561(4) 0.59076(16) 0.0396(7) Uani 1 1 d . . . . .
C3 C 0.6744(8) 0.4320(4) 0.57434(19) 0.0492(9) Uani 1 1 d . . . . .
H3 H 0.7727 0.4772 0.5377 0.059 Uiso 1 1 calc R U . . .
C4 C 0.5462(8) 0.5415(5) 0.6118(2) 0.0570(10) Uani 1 1 d . . . . .
H4 H 0.5555 0.6591 0.5997 0.068 Uiso 1 1 calc R U . . .
C5 C 0.4046(8) 0.4773(5) 0.6671(2) 0.0536(9) Uani 1 1 d . . . . .
C6 C 0.3862(8) 0.2997(5) 0.68365(19) 0.0569(10) Uani 1 1 d . . . . .
H6 H 0.2897 0.2553 0.7207 0.068 Uiso 1 1 calc R U . . .
C7 C 0.5104(8) 0.1885(5) 0.64539(18) 0.0496(9) Uani 1 1 d . . . . .
H7 H 0.4953 0.0694 0.6562 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2839(9) 0.6110(7) 0.7067(2) 0.0721(12) Uani 1 1 d . . . . .
H8 H 0.2886 0.7232 0.6895 0.087 Uiso 1 1 calc R U . . .
C9 C 0.0833(9) 0.7213(6) 0.7937(3) 0.0717(13) Uani 1 1 d . . . . .
C10 C 0.0978(11) 0.7252(6) 0.8645(3) 0.0844(15) Uani 1 1 d . . . . .
H10 H 0.1734 0.6409 0.8881 0.101 Uiso 1 1 calc R U . . .
C11 C 0.0035(10) 0.8507(6) 0.9017(2) 0.0746(13) Uani 1 1 d . . . . .
H11 H 0.0199 0.8516 0.9503 0.090 Uiso 1 1 calc R U . . .
C12 C -0.1158(8) 0.9763(5) 0.8687(2) 0.0540(9) Uani 1 1 d . . . . .
C13 C -0.1373(8) 0.9772(6) 0.7971(2) 0.0644(11) Uani 1 1 d . . . . .
H13 H -0.2178 1.0600 0.7739 0.077 Uiso 1 1 calc R U . . .
C14 C -0.0326(9) 0.8476(7) 0.7594(2) 0.0758(13) Uani 1 1 d . . . . .
H14 H -0.0420 0.8476 0.7109 0.091 Uiso 1 1 calc R U . . .
C15 C -0.3422(9) 1.2198(6) 0.8798(2) 0.0710(12) Uani 1 1 d . . . . .
H15A H -0.5100 1.1560 0.8480 0.085 Uiso 1 1 calc R U . . .
H15B H -0.2136 1.3003 0.8535 0.085 Uiso 1 1 calc R U . . .
C16 C -0.4255(11) 1.3259(7) 0.9381(3) 0.1000(18) Uani 1 1 d . . . . .
H16A H -0.5197 1.4125 0.9187 0.150 Uiso 1 1 calc R U . . .
H16B H -0.5527 1.2447 0.9637 0.150 Uiso 1 1 calc R U . . .
H16C H -0.2576 1.3883 0.9691 0.150 Uiso 1 1 calc R U . . .
N1 N 0.1825(8) 0.5757(5) 0.7597(2) 0.0766(11) Uani 1 1 d . . . . .
O1 O 0.9273(6) 0.2118(3) 0.50031(14) 0.0602(8) Uani 1 1 d D . . . .
O2 O 0.7935(6) -0.0167(3) 0.56654(13) 0.0579(7) Uani 1 1 d . . . . .
O3 O -0.2039(6) 1.0940(4) 0.91161(14) 0.0661(8) Uani 1 1 d . . . . .
H1O H 1.007(9) 0.141(5) 0.474(2) 0.099 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.254(4) . ?
C1 O1 1.282(4) . ?
C1 C2 1.480(4) . ?
C2 C3 1.380(4) . ?
C2 C7 1.390(5) . ?
C3 C4 1.383(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(5) . ?
C5 C8 1.513(6) . ?
C6 C7 1.387(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.198(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.355(7) . ?
C9 C14 1.390(6) . ?
C9 N1 1.470(5) . ?
C10 C11 1.366(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(5) . ?
C11 H11 0.9300 . ?
C12 O3 1.367(4) . ?
C12 C13 1.371(5) . ?
C13 C14 1.424(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O3 1.427(5) . ?
C15 C16 1.501(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O1 H1O 0.913(19) . ?

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
O2 C1 O1 122.6(3) . . ?
O2 C1 C2 120.5(3) . . ?
O1 C1 C2 116.9(3) . . ?
C3 C2 C7 119.7(3) . . ?
C3 C2 C1 119.9(3) . . ?
C7 C2 C1 120.4(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 C8 116.0(4) . . ?
C6 C5 C8 124.7(4) . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 119.6(3) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
N1 C8 C5 121.5(5) . . ?
N1 C8 H8 119.2 . . ?
C5 C8 H8 119.2 . . ?
C10 C9 C14 118.4(4) . . ?
C10 C9 N1 115.8(4) . . ?
C14 C9 N1 125.7(4) . . ?
C9 C10 C11 121.2(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 121.4(4) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
O3 C12 C13 124.4(4) . . ?
O3 C12 C11 116.0(3) . . ?
C13 C12 C11 119.6(3) . . ?
C12 C13 C14 118.1(4) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
C9 C14 C13 121.3(4) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
O3 C15 C16 106.9(4) . . ?
O3 C15 H15A 110.3 . . ?
C16 C15 H15A 110.3 . . ?
O3 C15 H15B 110.3 . . ?
C16 C15 H15B 110.3 . . ?
H15A C15 H15B 108.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 N1 C9 115.4(4) . . ?
C1 O1 H1O 118(3) . . ?
C12 O3 C15 118.1(3) . . ?

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
O2 C1 C2 C3 178.1(3) . . . . ?
O1 C1 C2 C3 -2.5(5) . . . . ?
O2 C1 C2 C7 -0.8(5) . . . . ?
O1 C1 C2 C7 178.6(3) . . . . ?
C7 C2 C3 C4 0.1(5) . . . . ?
C1 C2 C3 C4 -178.9(3) . . . . ?
C2 C3 C4 C5 1.3(6) . . . . ?
C3 C4 C5 C6 -1.6(6) . . . . ?
C3 C4 C5 C8 177.3(3) . . . . ?
C4 C5 C6 C7 0.5(6) . . . . ?
C8 C5 C6 C7 -178.2(4) . . . . ?
C5 C6 C7 C2 0.9(6) . . . . ?
C3 C2 C7 C6 -1.2(5) . . . . ?
C1 C2 C7 C6 177.8(3) . . . . ?
C4 C5 C8 N1 -172.4(4) . . . . ?
C6 C5 C8 N1 6.4(7) . . . . ?
C14 C9 C10 C11 -0.5(8) . . . . ?
N1 C9 C10 C11 -177.9(4) . . . . ?
C9 C10 C11 C12 1.3(8) . . . . ?
C10 C11 C12 O3 179.6(4) . . . . ?
C10 C11 C12 C13 -0.8(7) . . . . ?
O3 C12 C13 C14 179.2(4) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C10 C9 C14 C13 -0.8(7) . . . . ?
N1 C9 C14 C13 176.4(4) . . . . ?
C12 C13 C14 C9 1.2(6) . . . . ?
C5 C8 N1 C9 177.9(4) . . . . ?
C10 C9 N1 C8 -149.6(5) . . . . ?
C14 C9 N1 C8 33.2(6) . . . . ?
C13 C12 O3 C15 3.7(6) . . . . ?
C11 C12 O3 C15 -176.7(4) . . . . ?
C16 C15 O3 C12 177.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O2 0.913(19) 1.73(2) 2.633(3) 171(5) 2_756

_refine_diff_density_max         0.916
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_Compound9
_database_code_depnum_ccdc_archive 'CCDC 1533450'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-12-19 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         'C26 H22 O4 Sn'
_chemical_formula_sum            'C26 H22 O4 Sn'
_chemical_formula_weight         517.12

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.5925(2)
_cell_length_b                   19.0045(4)
_cell_length_c                   11.3877(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.160(2)
_cell_angle_gamma                90
_cell_volume                     2279.17(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4400
_cell_measurement_theta_max      28.5820
_cell_measurement_theta_min      3.7450

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    1.150
_shelx_estimated_absorpt_T_min   0.732
_shelx_estimated_absorpt_T_max   0.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9877
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.511
_diffrn_reflns_theta_max         28.718
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5183
_reflns_number_gt                4426
_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_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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)+(0.0241P)²+0.3239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5183
_refine_ls_number_parameters     286
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0571
_refine_ls_wR_factor_gt          0.0536
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.002

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 0.88065(18) 0.83692(11) 0.60845(18) 0.0345(4) Uani 1 1 d . . . . .
C2 C 0.98467(18) 0.89135(11) 0.61840(17) 0.0332(4) Uani 1 1 d . . . . .
C3 C 0.9638(2) 0.95180(13) 0.6814(2) 0.0498(6) Uani 1 1 d . . . . .
H3 H 0.8904 0.9558 0.7189 0.060 Uiso 1 1 calc R U . . .
C4 C 1.0500(3) 1.00581(14) 0.6890(3) 0.0625(7) Uani 1 1 d . . . . .
H4 H 1.0337 1.0465 0.7303 0.075 Uiso 1 1 calc R U . . .
C5 C 1.1606(3) 1.00037(14) 0.6361(2) 0.0640(7) Uani 1 1 d . . . . .
H5 H 1.2192 1.0370 0.6420 0.077 Uiso 1 1 calc R U . . .
C6 C 1.1835(2) 0.94054(14) 0.5748(2) 0.0534(6) Uani 1 1 d . . . . .
H6 H 1.2588 0.9364 0.5402 0.064 Uiso 1 1 calc R U . . .
C7 C 1.09545(19) 0.88578(11) 0.56341(18) 0.0372(5) Uani 1 1 d . . . . .
C8 C 1.1247(2) 0.82249(14) 0.4982(2) 0.0515(6) Uani 1 1 d . . . . .
H8 H 1.0716 0.7837 0.5007 0.062 Uiso 1 1 calc R U . . .
C9 C 0.65141(19) 0.81692(10) 0.28435(16) 0.0331(4) Uani 1 1 d . . . . .
C10 C 0.5442(2) 0.83994(12) 0.21457(19) 0.0460(5) Uani 1 1 d . . . . .
H10 H 0.4658 0.8387 0.2444 0.055 Uiso 1 1 calc R U . . .
C11 C 0.5518(3) 0.86483(14) 0.1010(2) 0.0597(7) Uani 1 1 d . . . . .
H11 H 0.4791 0.8808 0.0556 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6668(3) 0.86587(13) 0.0558(2) 0.0583(7) Uani 1 1 d . . . . .
H12 H 0.6717 0.8818 -0.0208 0.070 Uiso 1 1 calc R U . . .
C13 C 0.7741(3) 0.84363(14) 0.1229(2) 0.0542(6) Uani 1 1 d . . . . .
H13 H 0.8518 0.8447 0.0919 0.065 Uiso 1 1 calc R U . . .
C14 C 0.7673(2) 0.81933(12) 0.23744(19) 0.0434(5) Uani 1 1 d . . . . .
H14 H 0.8408 0.8046 0.2829 0.052 Uiso 1 1 calc R U . . .
C15 C 0.56366(18) 0.85096(11) 0.58384(17) 0.0348(4) Uani 1 1 d . . . . .
C16 C 0.5847(2) 0.92247(13) 0.5844(2) 0.0535(6) Uani 1 1 d . . . . .
H16 H 0.6280 0.9426 0.5260 0.064 Uiso 1 1 calc R U . . .
C17 C 0.5418(3) 0.96503(15) 0.6712(3) 0.0717(8) Uani 1 1 d . . . . .
H17 H 0.5569 1.0132 0.6708 0.086 Uiso 1 1 calc R U . . .
C18 C 0.4776(3) 0.93606(19) 0.7567(3) 0.0751(9) Uani 1 1 d . . . . .
H18 H 0.4494 0.9645 0.8149 0.090 Uiso 1 1 calc R U . . .
C19 C 0.4549(3) 0.86609(18) 0.7570(2) 0.0707(8) Uani 1 1 d . . . . .
H19 H 0.4105 0.8465 0.8151 0.085 Uiso 1 1 calc R U . . .
C20 C 0.4977(2) 0.82365(14) 0.6713(2) 0.0529(6) Uani 1 1 d . . . . .
H20 H 0.4816 0.7756 0.6725 0.064 Uiso 1 1 calc R U . . .
C21 C 0.67690(18) 0.67765(11) 0.51522(18) 0.0347(4) Uani 1 1 d . . . . .
C22 C 0.6962(2) 0.66068(12) 0.63451(18) 0.0396(5) Uani 1 1 d . . . . .
H22 H 0.6970 0.6961 0.6909 0.048 Uiso 1 1 calc R U . . .
C23 C 0.7141(2) 0.59140(13) 0.6700(2) 0.0501(6) Uani 1 1 d . . . . .
H23 H 0.7252 0.5805 0.7501 0.060 Uiso 1 1 calc R U . . .
C24 C 0.7156(3) 0.53901(13) 0.5885(2) 0.0622(7) Uani 1 1 d . . . . .
H24 H 0.7290 0.4927 0.6131 0.075 Uiso 1 1 calc R U . . .
C25 C 0.6973(3) 0.55435(14) 0.4707(2) 0.0686(8) Uani 1 1 d . . . . .
H25 H 0.6986 0.5186 0.4151 0.082 Uiso 1 1 calc R U . . .
C26 C 0.6768(3) 0.62362(13) 0.4342(2) 0.0542(6) Uani 1 1 d . . . . .
H26 H 0.6629 0.6337 0.3539 0.065 Uiso 1 1 calc R U . . .
O1 O 0.83297(13) 0.82449(9) 0.50140(12) 0.0422(4) Uani 1 1 d . . . . .
O2 O 0.84317(14) 0.81123(9) 0.69592(13) 0.0488(4) Uani 1 1 d . . . . .
O3 O 1.21419(19) 0.81805(12) 0.44146(18) 0.0760(6) Uani 1 1 d . . . . .
O4 O 0.43166(15) 0.74316(10) 0.40658(14) 0.0442(4) Uani 1 1 d D . . . .
Sn1 Sn 0.64248(2) 0.78335(2) 0.46210(2) 0.03139(5) Uani 1 1 d . . . . .
H41 H 0.409(2) 0.7207(11) 0.3432(17) 0.047 Uiso 1 1 d D U . . .
H42 H 0.371(2) 0.7684(13) 0.420(2) 0.047 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.214(2) . ?
C1 O1 1.290(2) . ?
C1 C2 1.507(3) . ?
C2 C3 1.385(3) . ?
C2 C7 1.392(3) . ?
C3 C4 1.370(3) . ?
C4 C5 1.378(4) . ?
C5 C6 1.369(4) . ?
C6 C7 1.394(3) . ?
C7 C8 1.464(3) . ?
C8 O3 1.206(3) . ?
C9 C10 1.385(3) . ?
C9 C14 1.392(3) . ?
C9 Sn1 2.1341(19) . ?
C10 C11 1.387(3) . ?
C11 C12 1.373(4) . ?
C12 C13 1.366(4) . ?
C13 C14 1.393(3) . ?
C15 C16 1.377(3) . ?
C15 C20 1.378(3) . ?
C15 Sn1 2.126(2) . ?
C16 C17 1.391(4) . ?
C17 C18 1.362(4) . ?
C18 C19 1.351(4) . ?
C19 C20 1.380(3) . ?
C21 C26 1.380(3) . ?
C21 C22 1.390(3) . ?
C21 Sn1 2.118(2) . ?
C22 C23 1.384(3) . ?
C23 C24 1.362(3) . ?
C24 C25 1.366(4) . ?
C25 C26 1.391(3) . ?
O1 Sn1 2.1656(14) . ?
O4 Sn1 2.3804(15) . ?

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
O2 C1 O1 124.92(19) . . ?
O2 C1 C2 121.03(18) . . ?
O1 C1 C2 113.93(17) . . ?
C3 C2 C7 119.0(2) . . ?
C3 C2 C1 116.92(19) . . ?
C7 C2 C1 123.98(19) . . ?
C4 C3 C2 120.8(2) . . ?
C3 C4 C5 120.5(3) . . ?
C6 C5 C4 119.4(2) . . ?
C5 C6 C7 120.9(2) . . ?
C2 C7 C6 119.3(2) . . ?
C2 C7 C8 121.7(2) . . ?
C6 C7 C8 119.0(2) . . ?
O3 C8 C7 123.4(3) . . ?
C10 C9 C14 118.19(19) . . ?
C10 C9 Sn1 121.42(16) . . ?
C14 C9 Sn1 120.32(15) . . ?
C9 C10 C11 121.1(2) . . ?
C12 C11 C10 119.8(2) . . ?
C13 C12 C11 120.3(2) . . ?
C12 C13 C14 120.2(2) . . ?
C9 C14 C13 120.4(2) . . ?
C16 C15 C20 117.6(2) . . ?
C16 C15 Sn1 121.66(17) . . ?
C20 C15 Sn1 120.58(17) . . ?
C15 C16 C17 120.8(3) . . ?
C18 C17 C16 119.9(3) . . ?
C19 C18 C17 120.2(3) . . ?
C18 C19 C20 120.1(3) . . ?
C15 C20 C19 121.4(3) . . ?
C26 C21 C22 118.1(2) . . ?
C26 C21 Sn1 121.79(16) . . ?
C22 C21 Sn1 120.13(16) . . ?
C23 C22 C21 120.5(2) . . ?
C24 C23 C22 120.5(2) . . ?
C23 C24 C25 120.2(2) . . ?
C24 C25 C26 119.8(2) . . ?
C21 C26 C25 121.0(2) . . ?
C1 O1 Sn1 121.53(13) . . ?
C21 Sn1 C15 117.04(8) . . ?
C21 Sn1 C9 122.05(8) . . ?
C15 Sn1 C9 119.89(8) . . ?
C21 Sn1 O1 98.94(7) . . ?
C15 Sn1 O1 93.98(7) . . ?
C9 Sn1 O1 87.30(7) . . ?
C21 Sn1 O4 84.23(7) . . ?
C15 Sn1 O4 86.80(7) . . ?
C9 Sn1 O4 88.84(7) . . ?
O1 Sn1 O4 175.93(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O1 0.93 2.64 3.095(3) 110.5 .
O4 H41 O2 0.851(16) 1.847(17) 2.687(2) 168(2) 4_575
O4 H42 O3 0.83(2) 1.95(3) 2.772(3) 172(2) 1_455

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_Compound5
_database_code_depnum_ccdc_archive 'CCDC 1533447'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-12-19 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         'C33 H27 N O3 Sn'
_chemical_formula_sum            'C33 H27 N O3 Sn'
_chemical_formula_weight         604.24

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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+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                   8.3521(3)
_cell_length_b                   17.4627(6)
_cell_length_c                   38.415(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5602.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4496
_cell_measurement_theta_max      28.0650
_cell_measurement_theta_min      3.9360

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             2448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.946
_shelx_estimated_absorpt_T_min   0.715
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20102
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.137
_diffrn_reflns_theta_max         28.726
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6563
_reflns_number_gt                4832
_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_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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)+17.9778P] 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         6563
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.004
_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 0.1260(6) 0.3328(3) 0.87177(14) 0.0458(11) Uani 1 1 d . . . . .
C2 C 0.1772(6) 0.3826(3) 0.90095(13) 0.0431(11) Uani 1 1 d . . . . .
C3 C 0.1275(7) 0.3687(3) 0.93452(14) 0.0560(14) Uani 1 1 d . . . . .
H3 H 0.0640 0.3262 0.9393 0.067 Uiso 1 1 calc R U . . .
C4 C 0.1718(8) 0.4176(3) 0.96118(14) 0.0649(16) Uani 1 1 d . . . . .
H4 H 0.1389 0.4074 0.9838 0.078 Uiso 1 1 calc R U . . .
C5 C 0.2642(7) 0.4814(3) 0.95457(14) 0.0547(13) Uani 1 1 d . . . . .
C6 C 0.3164(7) 0.4943(3) 0.92122(15) 0.0598(15) Uani 1 1 d . . . . .
H6 H 0.3819 0.5362 0.9166 0.072 Uiso 1 1 calc R U . . .
C7 C 0.2729(7) 0.4458(3) 0.89430(15) 0.0578(14) Uani 1 1 d . . . . .
H7 H 0.3078 0.4557 0.8718 0.069 Uiso 1 1 calc R U . . .
C8 C 0.3062(7) 0.5328(3) 0.98350(15) 0.0650(16) Uani 1 1 d . . . . .
H8 H 0.2823 0.5169 1.0060 0.078 Uiso 1 1 calc R U . . .
C9 C 0.4041(7) 0.6431(3) 1.00938(15) 0.0554(13) Uani 1 1 d . . . . .
C10 C 0.3336(9) 0.6330(4) 1.04143(18) 0.088(2) Uani 1 1 d . . . . .
H10 H 0.2562 0.5952 1.0442 0.106 Uiso 1 1 calc R U . . .
C11 C 0.3754(9) 0.6775(4) 1.06923(18) 0.093(2) Uani 1 1 d . . . . .
H11 H 0.3265 0.6694 1.0907 0.111 Uiso 1 1 calc R U . . .
C12 C 0.4885(7) 0.7338(3) 1.06593(15) 0.0595(14) Uani 1 1 d . . . . .
C13 C 0.5546(7) 0.7470(3) 1.03409(15) 0.0626(15) Uani 1 1 d . . . . .
H13 H 0.6284 0.7864 1.0312 0.075 Uiso 1 1 calc R U . . .
C14 C 0.5116(7) 0.7018(3) 1.00602(15) 0.0630(15) Uani 1 1 d . . . . .
H14 H 0.5568 0.7115 0.9843 0.076 Uiso 1 1 calc R U . . .
C15 C 0.6351(8) 0.8341(4) 1.09382(18) 0.085(2) Uani 1 1 d . . . . .
H15A H 0.6524 0.8551 1.1166 0.127 Uiso 1 1 calc R U . . .
H15B H 0.7353 0.8168 1.0844 0.127 Uiso 1 1 calc R U . . .
H15C H 0.5905 0.8727 1.0789 0.127 Uiso 1 1 calc R U . . .
C16 C -0.1679(6) 0.1316(3) 0.86324(13) 0.0464(12) Uani 1 1 d . . . . .
C17 C -0.2498(9) 0.0752(4) 0.84531(17) 0.0784(19) Uani 1 1 d . . . . .
H17 H -0.2505 0.0757 0.8211 0.094 Uiso 1 1 calc R U . . .
C18 C -0.3313(9) 0.0175(4) 0.8630(2) 0.090(2) Uani 1 1 d . . . . .
H18 H -0.3861 -0.0201 0.8507 0.108 Uiso 1 1 calc R U . . .
C19 C -0.3303(8) 0.0165(4) 0.8980(2) 0.088(2) Uani 1 1 d . . . . .
H19 H -0.3848 -0.0218 0.9099 0.106 Uiso 1 1 calc R U . . .
C20 C -0.2496(9) 0.0717(4) 0.91622(18) 0.086(2) Uani 1 1 d . . . . .
H20 H -0.2496 0.0706 0.9404 0.104 Uiso 1 1 calc R U . . .
C21 C -0.1679(7) 0.1293(3) 0.89884(15) 0.0619(15) Uani 1 1 d . . . . .
H21 H -0.1129 0.1665 0.9114 0.074 Uiso 1 1 calc R U . . .
C22 C 0.1564(6) 0.1678(3) 0.80944(12) 0.0464(12) Uani 1 1 d . . . . .
C23 C 0.2595(7) 0.2083(3) 0.78817(14) 0.0600(14) Uani 1 1 d . . . . .
H23 H 0.2433 0.2605 0.7847 0.072 Uiso 1 1 calc R U . . .
C24 C 0.3859(8) 0.1724(4) 0.77201(17) 0.0774(19) Uani 1 1 d . . . . .
H24 H 0.4536 0.2003 0.7576 0.093 Uiso 1 1 calc R U . . .
C25 C 0.4126(8) 0.0957(4) 0.77710(19) 0.084(2) Uani 1 1 d . . . . .
H25 H 0.4990 0.0718 0.7664 0.100 Uiso 1 1 calc R U . . .
C26 C 0.3125(8) 0.0546(4) 0.79787(18) 0.0764(19) Uani 1 1 d . . . . .
H26 H 0.3306 0.0026 0.8014 0.092 Uiso 1 1 calc R U . . .
C27 C 0.1835(7) 0.0902(3) 0.81384(15) 0.0604(15) Uani 1 1 d . . . . .
H27 H 0.1144 0.0616 0.8277 0.073 Uiso 1 1 calc R U . . .
C28 C -0.1937(6) 0.2999(3) 0.81249(12) 0.0422(11) Uani 1 1 d . . . . .
C29 C -0.3503(6) 0.3051(3) 0.82388(14) 0.0580(14) Uani 1 1 d . . . . .
H29 H -0.3887 0.2698 0.8400 0.070 Uiso 1 1 calc R U . . .
C30 C -0.4512(7) 0.3624(4) 0.81164(16) 0.0652(16) Uani 1 1 d . . . . .
H30 H -0.5555 0.3662 0.8199 0.078 Uiso 1 1 calc R U . . .
C31 C -0.3954(7) 0.4133(4) 0.78722(17) 0.0667(16) Uani 1 1 d . . . . .
H31 H -0.4626 0.4514 0.7787 0.080 Uiso 1 1 calc R U . . .
C32 C -0.2424(8) 0.4081(4) 0.77539(16) 0.0693(16) Uani 1 1 d . . . . .
H32 H -0.2059 0.4425 0.7587 0.083 Uiso 1 1 calc R U . . .
C33 C -0.1407(7) 0.3521(3) 0.78798(14) 0.0590(14) Uani 1 1 d . . . . .
H33 H -0.0359 0.3495 0.7799 0.071 Uiso 1 1 calc R U . . .
N1 N 0.3720(6) 0.5965(3) 0.97976(12) 0.0625(13) Uani 1 1 d . . . . .
O1 O 0.1608(4) 0.3468(2) 0.84140(10) 0.0571(9) Uani 1 1 d . . . . .
O2 O 0.0398(4) 0.27325(19) 0.88037(9) 0.0534(9) Uani 1 1 d . . . . .
O3 O 0.5280(6) 0.7716(3) 1.09613(10) 0.0829(13) Uani 1 1 d . . . . .
Sn1 Sn -0.03959(4) 0.21857(2) 0.83617(2) 0.04278(10) 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 O1 1.227(6) . ?
C1 O2 1.307(6) . ?
C1 C2 1.482(7) . ?
C2 C3 1.376(7) . ?
C2 C7 1.387(7) . ?
C3 C4 1.385(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(7) . ?
C5 C8 1.471(7) . ?
C6 C7 1.385(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.249(7) . ?
C8 H8 0.9300 . ?
C9 C14 1.369(7) . ?
C9 C10 1.376(8) . ?
C9 N1 1.424(7) . ?
C10 C11 1.366(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(7) . ?
C12 O3 1.375(6) . ?
C13 C14 1.384(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O3 1.414(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.368(7) . ?
C16 C17 1.383(7) . ?
C16 Sn1 2.130(5) . ?
C17 C18 1.393(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.344(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(8) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.381(7) . ?
C22 C27 1.385(7) . ?
C22 Sn1 2.126(5) . ?
C23 C24 1.376(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.360(9) . ?
C25 H25 0.9300 . ?
C26 C27 1.388(8) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.382(7) . ?
C28 C33 1.384(7) . ?
C28 Sn1 2.121(5) . ?
C29 C30 1.390(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.374(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.359(8) . ?
C31 H31 0.9300 . ?
C32 C33 1.383(8) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
O2 Sn1 2.058(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
O1 C1 O2 122.0(5) . . ?
O1 C1 C2 122.3(5) . . ?
O2 C1 C2 115.7(4) . . ?
C3 C2 C7 119.1(5) . . ?
C3 C2 C1 121.2(5) . . ?
C7 C2 C1 119.6(5) . . ?
C2 C3 C4 120.2(5) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 118.9(5) . . ?
C6 C5 C8 121.9(5) . . ?
C4 C5 C8 119.2(5) . . ?
C5 C6 C7 120.8(5) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 120.0(5) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
N1 C8 C5 124.2(6) . . ?
N1 C8 H8 117.9 . . ?
C5 C8 H8 117.9 . . ?
C14 C9 C10 117.5(5) . . ?
C14 C9 N1 118.4(5) . . ?
C10 C9 N1 124.2(5) . . ?
C11 C10 C9 121.1(6) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.8(6) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.0(5) . . ?
C13 C12 O3 125.4(5) . . ?
C11 C12 O3 115.6(6) . . ?
C12 C13 C14 119.9(5) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C13 121.6(6) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 118.5(5) . . ?
C21 C16 Sn1 120.6(4) . . ?
C17 C16 Sn1 120.9(4) . . ?
C16 C17 C18 120.9(6) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 119.6(6) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.4(6) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C21 120.5(6) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.1(6) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C27 118.1(5) . . ?
C23 C22 Sn1 123.5(4) . . ?
C27 C22 Sn1 118.3(4) . . ?
C24 C23 C22 120.8(6) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 120.4(7) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 119.9(6) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.0(6) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C22 120.8(6) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?
C29 C28 C33 118.3(5) . . ?
C29 C28 Sn1 118.9(4) . . ?
C33 C28 Sn1 122.6(4) . . ?
C28 C29 C30 121.0(5) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C31 C30 C29 119.4(5) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C32 C31 C30 120.3(6) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C33 120.5(6) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C32 C33 C28 120.5(5) . . ?
C32 C33 H33 119.7 . . ?
C28 C33 H33 119.7 . . ?
C8 N1 C9 119.9(5) . . ?
C1 O2 Sn1 109.7(3) . . ?
C12 O3 C15 118.0(5) . . ?
O2 Sn1 C28 103.81(16) . . ?
O2 Sn1 C22 110.11(17) . . ?
C28 Sn1 C22 122.63(18) . . ?
O2 Sn1 C16 95.16(17) . . ?
C28 Sn1 C16 112.41(19) . . ?
C22 Sn1 C16 109.04(19) . . ?

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
O1 C1 C2 C3 175.4(5) . . . . ?
O2 C1 C2 C3 -3.8(7) . . . . ?
O1 C1 C2 C7 -2.6(7) . . . . ?
O2 C1 C2 C7 178.2(4) . . . . ?
C7 C2 C3 C4 0.5(8) . . . . ?
C1 C2 C3 C4 -177.5(5) . . . . ?
C2 C3 C4 C5 0.9(9) . . . . ?
C3 C4 C5 C6 -2.2(9) . . . . ?
C3 C4 C5 C8 178.8(5) . . . . ?
C4 C5 C6 C7 2.2(9) . . . . ?
C8 C5 C6 C7 -178.8(5) . . . . ?
C5 C6 C7 C2 -0.9(9) . . . . ?
C3 C2 C7 C6 -0.4(8) . . . . ?
C1 C2 C7 C6 177.6(5) . . . . ?
C6 C5 C8 N1 10.2(10) . . . . ?
C4 C5 C8 N1 -170.9(6) . . . . ?
C14 C9 C10 C11 -3.2(11) . . . . ?
N1 C9 C10 C11 176.9(7) . . . . ?
C9 C10 C11 C12 0.3(13) . . . . ?
C10 C11 C12 C13 2.6(11) . . . . ?
C10 C11 C12 O3 -176.1(7) . . . . ?
C11 C12 C13 C14 -2.5(9) . . . . ?
O3 C12 C13 C14 176.0(6) . . . . ?
C10 C9 C14 C13 3.3(9) . . . . ?
N1 C9 C14 C13 -176.8(5) . . . . ?
C12 C13 C14 C9 -0.4(9) . . . . ?
C21 C16 C17 C18 0.4(10) . . . . ?
Sn1 C16 C17 C18 178.8(5) . . . . ?
C16 C17 C18 C19 -0.1(12) . . . . ?
C17 C18 C19 C20 -0.1(12) . . . . ?
C18 C19 C20 C21 0.0(12) . . . . ?
C17 C16 C21 C20 -0.5(9) . . . . ?
Sn1 C16 C21 C20 -178.9(5) . . . . ?
C19 C20 C21 C16 0.3(11) . . . . ?
C27 C22 C23 C24 -0.4(8) . . . . ?
Sn1 C22 C23 C24 179.0(4) . . . . ?
C22 C23 C24 C25 -0.7(10) . . . . ?
C23 C24 C25 C26 0.8(11) . . . . ?
C24 C25 C26 C27 0.1(10) . . . . ?
C25 C26 C27 C22 -1.2(9) . . . . ?
C23 C22 C27 C26 1.3(8) . . . . ?
Sn1 C22 C27 C26 -178.0(4) . . . . ?
C33 C28 C29 C30 -1.4(8) . . . . ?
Sn1 C28 C29 C30 173.6(4) . . . . ?
C28 C29 C30 C31 1.6(9) . . . . ?
C29 C30 C31 C32 -0.6(9) . . . . ?
C30 C31 C32 C33 -0.6(10) . . . . ?
C31 C32 C33 C28 0.8(10) . . . . ?
C29 C28 C33 C32 0.2(8) . . . . ?
Sn1 C28 C33 C32 -174.6(4) . . . . ?
C5 C8 N1 C9 178.3(5) . . . . ?
C14 C9 N1 C8 163.1(6) . . . . ?
C10 C9 N1 C8 -17.0(9) . . . . ?
O1 C1 O2 Sn1 -5.5(6) . . . . ?
C2 C1 O2 Sn1 173.8(3) . . . . ?
C13 C12 O3 C15 6.1(9) . . . . ?
C11 C12 O3 C15 -175.4(6) . . . . ?

_refine_diff_density_max         1.024
_refine_diff_density_min         -2.565
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_HL5
_database_code_depnum_ccdc_archive 'CCDC 1533445'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-12-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT732_HL5                 
;
PROBLEM: Angle   Calc      120(3), Rep   120.00(5) ......       9.90 s.u.-R
RESPONSE: "One of the molecules of the compound is highly disordered. Some of the atoms of one of the aromatic  rings were difficult to locate and were included in the model by means of the AFIX instruction. SIMU and DELU restrains had to be used to make the ADP values of the atoms more reasonable."
;
# Added during the CSD deposition process: Friday 17 February 2017 02:47 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P 21 c a'
_space_group_name_Hall           'P -2ac 2a'

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

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

_cell_length_a                   6.1246(5)
_cell_length_b                   57.377(4)
_cell_length_c                   7.2367(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2543.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2347
_cell_measurement_theta_max      28.4020
_cell_measurement_theta_min      3.9700

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13265
_diffrn_reflns_av_unetI/netI     0.0915
_diffrn_reflns_av_R_equivalents  0.1330
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -69
_diffrn_reflns_limit_k_max       68
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.328
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4431
_reflns_number_gt                3727
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.38(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -2(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4431
_refine_ls_number_parameters     337
_refine_ls_number_restraints     197
_refine_ls_R_factor_all          0.1761
_refine_ls_R_factor_gt           0.1665
_refine_ls_wR_factor_ref         0.4293
_refine_ls_wR_factor_gt          0.4128
_refine_ls_goodness_of_fit_ref   1.713
_refine_ls_restrained_S_all      1.687
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.468(3) 0.2192(2) 0.5097(17) 0.071(3) Uani 1 1 d . U . . .
C2 C 0.547(2) 0.19525(17) 0.5027(11) 0.048(2) Uani 1 1 d . U . . .
C3 C 0.4181(18) 0.17835(17) 0.5664(13) 0.050(2) Uani 1 1 d . U . . .
H3 H 0.2791 0.1819 0.6098 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4951(14) 0.15454(14) 0.5676(10) 0.0365(18) Uani 1 1 d . U . . .
H4 H 0.4055 0.1426 0.6100 0.044 Uiso 1 1 calc R U . . .
C5 C 0.7048(13) 0.14975(13) 0.5047(9) 0.0315(18) Uani 1 1 d . U . . .
C6 C 0.8308(17) 0.16714(15) 0.4396(11) 0.042(2) Uani 1 1 d . U . . .
H6 H 0.9677 0.1636 0.3914 0.050 Uiso 1 1 calc R U . . .
C7 C 0.7596(19) 0.19108(15) 0.4423(13) 0.048(2) Uani 1 1 d . U . . .
H7 H 0.8510 0.2032 0.4055 0.058 Uiso 1 1 calc R U . . .
C8 C 0.7828(13) 0.12551(12) 0.5131(8) 0.0286(16) Uani 1 1 d . U . . .
H8 H 0.6841 0.1136 0.5379 0.034 Uiso 1 1 calc R U . . .
C9 C 1.0516(11) 0.09659(10) 0.4976(7) 0.0165(14) Uani 1 1 d . U . . .
C10 C 0.9375(11) 0.07885(10) 0.5887(7) 0.0208(14) Uani 1 1 d . U . . .
H10 H 0.8073 0.0823 0.6490 0.025 Uiso 1 1 calc R U . . .
C11 C 1.0174(10) 0.05600(11) 0.5899(7) 0.0200(15) Uani 1 1 d . U . . .
H11 H 0.9405 0.0442 0.6487 0.024 Uiso 1 1 calc R U . . .
C12 C 1.2142(11) 0.05135(9) 0.5013(6) 0.0138(14) Uani 1 1 d . U . . .
C13 C 1.3308(11) 0.06858(11) 0.4122(7) 0.0200(14) Uani 1 1 d . U . . .
H13 H 1.4613 0.0652 0.3522 0.024 Uiso 1 1 calc R U . . .
C14 C 1.2469(10) 0.09126(10) 0.4147(7) 0.0188(14) Uani 1 1 d . U . . .
H14 H 1.3261 0.1031 0.3584 0.023 Uiso 1 1 calc R U . . .
C15 C 1.4771(15) 0.02187(13) 0.4204(13) 0.047(2) Uani 1 1 d . . . . .
H15A H 1.4610 0.0244 0.2900 0.070 Uiso 1 1 calc R U . . .
H15B H 1.5086 0.0057 0.4428 0.070 Uiso 1 1 calc R U . . .
H15C H 1.5946 0.0313 0.4666 0.070 Uiso 1 1 calc R U . . .
C21 C 0.226(3) 0.2813(3) 0.498(2) 0.088(5) Uani 1 1 d . U . . .
C22 C 0.131(3) 0.3042(3) 0.492(2) 0.092(5) Uani 1 1 d . U . . .
C23 C 0.265(3) 0.3245(3) 0.432(2) 0.092(4) Uani 1 1 d . U . . .
H23 H 0.4076 0.3227 0.3913 0.111 Uiso 1 1 calc R U . . .
C24 C 0.169(4) 0.3460(4) 0.441(2) 0.105(5) Uani 1 1 d . U . . .
H24 H 0.2519 0.3585 0.3994 0.125 Uiso 1 1 calc R U . . .
C25 C -0.031(4) 0.3511(3) 0.503(3) 0.104(5) Uani 1 1 d . U . . .
C26 C -0.158(4) 0.3307(3) 0.559(2) 0.100(4) Uani 1 1 d . U . . .
H26 H -0.3023 0.3326 0.5956 0.120 Uiso 1 1 calc R U . . .
C27 C -0.077(3) 0.3110(3) 0.558(2) 0.093(4) Uani 1 1 d . U . . .
H27 H -0.1634 0.2991 0.6062 0.112 Uiso 1 1 calc R U . . .
C28 C -0.114(6) 0.3743(5) 0.491(4) 0.143(10) Uani 1 1 d . U . . .
H28 H -0.0129 0.3860 0.4665 0.172 Uiso 1 1 calc R U . . .
C29 C -0.358(5) 0.4047(5) 0.496(3) 0.193(15) Uani 1 1 d G U . . .
C30 C -0.247(4) 0.4229(7) 0.410(3) 0.202(15) Uani 1 1 d G U . . .
H30 H -0.1144 0.4201 0.3512 0.242 Uiso 1 1 calc R U . . .
C31 C -0.334(6) 0.4452(6) 0.412(3) 0.218(15) Uani 1 1 d G U . . .
H31 H -0.2604 0.4574 0.3542 0.261 Uiso 1 1 calc R U . . .
C32 C -0.533(6) 0.4494(5) 0.499(3) 0.212(15) Uani 1 1 d DG U . . .
C33 C -0.643(4) 0.4312(6) 0.585(3) 0.207(14) Uani 1 1 d DG U . . .
H33 H -0.7757 0.4340 0.6438 0.248 Uiso 1 1 calc R U . . .
C34 C -0.556(5) 0.4089(5) 0.583(3) 0.205(14) Uani 1 1 d G U . . .
H34 H -0.6296 0.3967 0.6408 0.246 Uiso 1 1 calc R U . . .
C35 C -0.771(5) 0.4818(6) 0.583(5) 0.200(18) Uani 1 1 d D . . . .
H35A H -0.8279 0.4701 0.6643 0.299 Uiso 1 1 calc R U . . .
H35B H -0.8772 0.4853 0.4896 0.299 Uiso 1 1 calc R U . . .
H35C H -0.7377 0.4956 0.6521 0.299 Uiso 1 1 calc R U . . .
N1 N 0.9844(10) 0.12054(10) 0.4869(7) 0.0252(15) Uani 1 1 d . . . . .
N2 N -0.299(6) 0.3802(7) 0.509(3) 0.171(11) Uani 1 1 d . . . . .
O1 O 0.588(3) 0.23571(19) 0.434(2) 0.109(4) Uani 1 1 d . . . . .
H1 H 0.5314 0.2484 0.4538 0.163 Uiso 1 1 calc R U . . .
O2 O 0.285(3) 0.2245(2) 0.5738(16) 0.109(4) Uani 1 1 d . . . . .
O3 O 1.2831(9) 0.02797(8) 0.5106(6) 0.0275(13) Uani 1 1 d . . . . .
O4 O 0.410(2) 0.2777(2) 0.4449(19) 0.096(3) Uani 1 1 d . . . . .
O5 O 0.096(4) 0.2647(3) 0.557(3) 0.155(8) Uani 1 1 d . . . . .
H5 H 0.1590 0.2521 0.5503 0.232 Uiso 1 1 calc R U . . .
O6 O -0.574(6) 0.4732(5) 0.496(4) 0.252(17) Uani 1 1 d 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 O2 1.25(2) . ?
C1 O1 1.31(2) . ?
C1 C2 1.459(15) . ?
C2 C3 1.333(16) . ?
C2 C7 1.393(16) . ?
C3 C4 1.445(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.347(13) . ?
C5 C8 1.471(10) . ?
C6 C7 1.441(11) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.281(10) . ?
C8 H8 0.9300 . ?
C9 C14 1.372(9) . ?
C9 C10 1.400(9) . ?
C9 N1 1.437(7) . ?
C10 C11 1.400(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(8) . ?
C12 O3 1.408(7) . ?
C13 C14 1.399(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O3 1.400(10) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C21 O4 1.21(2) . ?
C21 O5 1.31(3) . ?
C21 C22 1.44(3) . ?
C22 C27 1.41(3) . ?
C22 C23 1.49(2) . ?
C23 C24 1.37(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.33(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.47(3) . ?
C25 C28 1.43(3) . ?
C26 C27 1.23(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 N2 1.19(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.3900 . ?
C29 C34 1.3900 . ?
C29 N2 1.46(4) . ?
C30 C31 1.3900 . ?
C30 H30 0.9300 . ?
C31 C32 1.3900 . ?
C31 H31 0.9300 . ?
C32 O6 1.39(2) . ?
C32 C33 1.3900 . ?
C33 C34 1.3900 . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 O6 1.45(2) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
O1 H1 0.8200 . ?
O5 H5 0.8200 . ?

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
O2 C1 O1 118.8(13) . . ?
O2 C1 C2 122.4(14) . . ?
O1 C1 C2 118.6(14) . . ?
C3 C2 C7 122.5(9) . . ?
C3 C2 C1 118.5(11) . . ?
C7 C2 C1 118.8(11) . . ?
C2 C3 C4 119.8(9) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.1(8) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 119.8(7) . . ?
C6 C5 C8 121.9(8) . . ?
C4 C5 C8 118.3(7) . . ?
C5 C6 C7 121.9(9) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C2 C7 C6 116.8(9) . . ?
C2 C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
N1 C8 C5 121.1(7) . . ?
N1 C8 H8 119.4 . . ?
C5 C8 H8 119.4 . . ?
C14 C9 C10 118.6(5) . . ?
C14 C9 N1 116.1(5) . . ?
C10 C9 N1 125.3(6) . . ?
C9 C10 C11 120.6(5) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 118.7(5) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 121.8(5) . . ?
C13 C12 O3 123.4(6) . . ?
C11 C12 O3 114.9(5) . . ?
C12 C13 C14 118.1(5) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
C9 C14 C13 122.2(5) . . ?
C9 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C21 O5 123.3(18) . . ?
O4 C21 C22 121.4(16) . . ?
O5 C21 C22 115.2(18) . . ?
C27 C22 C21 127.2(16) . . ?
C27 C22 C23 112.3(16) . . ?
C21 C22 C23 120.1(17) . . ?
C24 C23 C22 117.1(19) . . ?
C24 C23 H23 121.5 . . ?
C22 C23 H23 121.5 . . ?
C25 C24 C23 127(2) . . ?
C25 C24 H24 116.3 . . ?
C23 C24 H24 116.3 . . ?
C24 C25 C26 114(2) . . ?
C24 C25 C28 121(2) . . ?
C26 C25 C28 125(3) . . ?
C27 C26 C25 121(2) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C22 127.9(19) . . ?
C26 C27 H27 116.0 . . ?
C22 C27 H27 116.0 . . ?
N2 C28 C25 127(4) . . ?
N2 C28 H28 116.7 . . ?
C25 C28 H28 116.7 . . ?
C30 C29 C34 120.0 . . ?
C30 C29 N2 129(3) . . ?
C34 C29 N2 111(3) . . ?
C31 C30 C29 120.00(5) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
O6 C32 C33 131(3) . . ?
O6 C32 C31 109(3) . . ?
C33 C32 C31 120.0 . . ?
C34 C33 C32 120.00(5) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C29 120.0 . . ?
C33 C34 H34 120.0 . . ?
C29 C34 H34 120.0 . . ?
O6 C35 H35A 109.5 . . ?
O6 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O6 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C8 N1 C9 118.8(6) . . ?
C28 N2 C29 120(3) . . ?
C1 O1 H1 109.5 . . ?
C15 O3 C12 118.1(5) . . ?
C21 O5 H5 109.5 . . ?
C32 O6 C35 119(3) . . ?

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
O2 C1 C2 C3 0.3(19) . . . . ?
O1 C1 C2 C3 -174.9(13) . . . . ?
O2 C1 C2 C7 -175.1(12) . . . . ?
O1 C1 C2 C7 9.6(18) . . . . ?
C7 C2 C3 C4 -2.4(14) . . . . ?
C1 C2 C3 C4 -177.7(9) . . . . ?
C2 C3 C4 C5 1.0(12) . . . . ?
C3 C4 C5 C6 -1.6(11) . . . . ?
C3 C4 C5 C8 177.9(7) . . . . ?
C4 C5 C6 C7 3.6(12) . . . . ?
C8 C5 C6 C7 -176.0(7) . . . . ?
C3 C2 C7 C6 4.1(14) . . . . ?
C1 C2 C7 C6 179.4(9) . . . . ?
C5 C6 C7 C2 -4.7(13) . . . . ?
C6 C5 C8 N1 11.3(10) . . . . ?
C4 C5 C8 N1 -168.2(7) . . . . ?
C14 C9 C10 C11 -2.1(8) . . . . ?
N1 C9 C10 C11 179.7(5) . . . . ?
C9 C10 C11 C12 1.0(8) . . . . ?
C10 C11 C12 C13 -0.4(8) . . . . ?
C10 C11 C12 O3 179.5(5) . . . . ?
C11 C12 C13 C14 0.8(8) . . . . ?
O3 C12 C13 C14 -179.1(5) . . . . ?
C10 C9 C14 C13 2.6(8) . . . . ?
N1 C9 C14 C13 -179.1(5) . . . . ?
C12 C13 C14 C9 -1.9(8) . . . . ?
O4 C21 C22 C27 -176.7(18) . . . . ?
O5 C21 C22 C27 7(3) . . . . ?
O4 C21 C22 C23 -5(3) . . . . ?
O5 C21 C22 C23 178.4(18) . . . . ?
C27 C22 C23 C24 -3(2) . . . . ?
C21 C22 C23 C24 -175.7(16) . . . . ?
C22 C23 C24 C25 2(3) . . . . ?
C23 C24 C25 C26 -3(3) . . . . ?
C23 C24 C25 C28 -176(2) . . . . ?
C24 C25 C26 C27 4(3) . . . . ?
C28 C25 C26 C27 177(2) . . . . ?
C25 C26 C27 C22 -6(3) . . . . ?
C21 C22 C27 C26 177.3(19) . . . . ?
C23 C22 C27 C26 5(3) . . . . ?
C24 C25 C28 N2 165(3) . . . . ?
C26 C25 C28 N2 -7(5) . . . . ?
C34 C29 C30 C31 0.0 . . . . ?
N2 C29 C30 C31 179(2) . . . . ?
C29 C30 C31 C32 0.0 . . . . ?
C30 C31 C32 O6 175(2) . . . . ?
C30 C31 C32 C33 0.0 . . . . ?
O6 C32 C33 C34 -173(3) . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C32 C33 C34 C29 0.0 . . . . ?
C30 C29 C34 C33 0.0 . . . . ?
N2 C29 C34 C33 -179.4(19) . . . . ?
C5 C8 N1 C9 179.7(5) . . . . ?
C14 C9 N1 C8 160.6(6) . . . . ?
C10 C9 N1 C8 -21.2(9) . . . . ?
C25 C28 N2 C29 179(2) . . . . ?
C30 C29 N2 C28 22(4) . . . . ?
C34 C29 N2 C28 -159(3) . . . . ?
C13 C12 O3 C15 -1.7(9) . . . . ?
C11 C12 O3 C15 178.4(6) . . . . ?
C33 C32 O6 C35 -5(5) . . . . ?
C31 C32 O6 C35 -179(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15B O3 0.96 2.58 3.455(9) 151.0 2_556
C35 H35B O6 0.96 2.67 3.23(4) 118.0 2_466
O1 H1 O4 0.82 1.84 2.648(15) 168.1 .
O5 H5 O2 0.82 1.77 2.584(17) 171.0 .

_refine_diff_density_max         1.306
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.236

####################################################################### 
# 
# 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_Compound10
_database_code_depnum_ccdc_archive 'CCDC 1533451'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-12-19 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         'C32 H25 N O2 Sn'
_chemical_formula_sum            'C32 H25 N O2 Sn'
_chemical_formula_weight         574.22

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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.6664(3)
_cell_length_b                   14.5629(6)
_cell_length_c                   19.7869(7)
_cell_angle_alpha                101.707(3)
_cell_angle_beta                 94.317(4)
_cell_angle_gamma                96.279(3)
_cell_volume                     2697.49(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7436
_cell_measurement_theta_max      27.0020
_cell_measurement_theta_min      3.6450

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.975
_shelx_estimated_absorpt_T_min   0.786
_shelx_estimated_absorpt_T_max   0.793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23758
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.101
_diffrn_reflns_theta_max         26.372
_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             11011
_reflns_number_gt                8792
_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_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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)+(0.0304P)²+1.2543P] 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         11011
_refine_ls_number_parameters     649
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0771
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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_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 0.6438(3) 0.8444(2) 0.97288(16) 0.0420(7) Uani 1 1 d . . . . .
C2 C 0.6756(3) 0.9346(2) 1.02508(15) 0.0394(7) Uani 1 1 d . . . . .
C3 C 0.8055(3) 0.9878(2) 1.02878(18) 0.0531(8) Uani 1 1 d . . . . .
H3 H 0.8677 0.9690 0.9966 0.064 Uiso 1 1 calc R U . . .
C4 C 0.8425(4) 1.0683(3) 1.0798(2) 0.0642(10) Uani 1 1 d . . . . .
H4 H 0.9305 1.1027 1.0828 0.077 Uiso 1 1 calc R U . . .
C5 C 0.7504(4) 1.0978(3) 1.1261(2) 0.0646(10) Uani 1 1 d . . . . .
H5 H 0.7763 1.1521 1.1606 0.078 Uiso 1 1 calc R U . . .
C6 C 0.6198(4) 1.0480(2) 1.12233(18) 0.0552(9) Uani 1 1 d . . . . .
H6 H 0.5575 1.0698 1.1536 0.066 Uiso 1 1 calc R U . . .
C7 C 0.5797(3) 0.9655(2) 1.07254(16) 0.0414(7) Uani 1 1 d . . . . .
C8 C 0.4352(3) 0.9174(2) 1.06704(16) 0.0427(7) Uani 1 1 d . . . . .
H8 H 0.3946 0.8811 1.0245 0.051 Uiso 1 1 calc R U . . .
C9 C 0.2245(3) 0.8812(2) 1.11110(18) 0.0520(8) Uani 1 1 d . . . . .
C10 C 0.1696(4) 0.8040(3) 1.0604(2) 0.0714(11) Uani 1 1 d . . . . .
H10 H 0.2263 0.7762 1.0283 0.086 Uiso 1 1 calc R U . . .
C11 C 0.0302(4) 0.7673(3) 1.0568(3) 0.0812(13) Uani 1 1 d . . . . .
H11 H -0.0063 0.7155 1.0217 0.097 Uiso 1 1 calc R U . . .
C12 C -0.0533(4) 0.8060(3) 1.1038(3) 0.0804(13) Uani 1 1 d . . . . .
H12 H -0.1464 0.7803 1.1016 0.096 Uiso 1 1 calc R U . . .
C13 C -0.0001(5) 0.8827(4) 1.1541(3) 0.0873(14) Uani 1 1 d . . . . .
H13 H -0.0579 0.9103 1.1857 0.105 Uiso 1 1 calc R U . . .
C14 C 0.1385(4) 0.9198(3) 1.1589(2) 0.0713(11) Uani 1 1 d . . . . .
H14 H 0.1742 0.9710 1.1945 0.086 Uiso 1 1 calc R U . . .
C21 C 0.8755(3) 0.8165(3) 0.46746(18) 0.0516(8) Uani 1 1 d . . . . .
C22 C 0.8492(3) 0.9038(2) 0.51710(17) 0.0510(8) Uani 1 1 d . . . . .
C23 C 0.7223(4) 0.9391(3) 0.5073(2) 0.0670(10) Uani 1 1 d . . . . .
H23 H 0.6592 0.9111 0.4689 0.080 Uiso 1 1 calc R U . . .
C24 C 0.6907(4) 1.0154(3) 0.5544(2) 0.0779(12) Uani 1 1 d . . . . .
H24 H 0.6054 1.0382 0.5484 0.094 Uiso 1 1 calc R U . . .
C25 C 0.7858(5) 1.0583(3) 0.6107(2) 0.0769(12) Uani 1 1 d . . . . .
H25 H 0.7641 1.1094 0.6428 0.092 Uiso 1 1 calc R U . . .
C26 C 0.9108(4) 1.0258(3) 0.6190(2) 0.0658(10) Uani 1 1 d . . . . .
H26 H 0.9747 1.0560 0.6565 0.079 Uiso 1 1 calc R U . . .
C27 C 0.9458(3) 0.9478(2) 0.57261(18) 0.0532(8) Uani 1 1 d . . . . .
C28 C 1.0866(4) 0.9200(3) 0.58099(19) 0.0574(9) Uani 1 1 d . . . . .
H28 H 1.1225 0.8861 0.5427 0.069 Uiso 1 1 calc R U . . .
C29 C 1.2968(4) 0.9130(3) 0.6428(2) 0.0647(10) Uani 1 1 d . . . . .
C30 C 1.3884(5) 0.9605(4) 0.6966(2) 0.1054(18) Uani 1 1 d . . . . .
H30 H 1.3602 1.0083 0.7294 0.126 Uiso 1 1 calc R U . . .
C31 C 1.5239(5) 0.9388(5) 0.7036(3) 0.122(2) Uani 1 1 d . . . . .
H31 H 1.5865 0.9744 0.7399 0.147 Uiso 1 1 calc R U . . .
C32 C 1.5660(5) 0.8692(4) 0.6601(3) 0.0934(15) Uani 1 1 d . . . . .
H32 H 1.6564 0.8540 0.6664 0.112 Uiso 1 1 calc R U . . .
C33 C 1.4769(6) 0.8201(4) 0.6063(4) 0.117(2) Uani 1 1 d . . . . .
H33 H 1.5064 0.7714 0.5749 0.141 Uiso 1 1 calc R U . . .
C34 C 1.3424(5) 0.8412(4) 0.5972(3) 0.116(2) Uani 1 1 d . . . . .
H34 H 1.2818 0.8065 0.5597 0.139 Uiso 1 1 calc R U . . .
C40 C 0.7554(3) 0.7150(2) 0.77304(16) 0.0474(8) Uani 1 1 d . . . . .
C41 C 0.8497(3) 0.7945(3) 0.77388(19) 0.0568(9) Uani 1 1 d . . . . .
H41 H 0.8643 0.8431 0.8132 0.068 Uiso 1 1 calc R U . . .
C42 C 0.9220(4) 0.8027(3) 0.7174(2) 0.0724(12) Uani 1 1 d . . . . .
H42 H 0.9853 0.8562 0.7191 0.087 Uiso 1 1 calc R U . . .
C43 C 0.9010(4) 0.7332(4) 0.6597(2) 0.0812(13) Uani 1 1 d . . . . .
H43 H 0.9487 0.7396 0.6215 0.097 Uiso 1 1 calc R U . . .
C44 C 0.8109(5) 0.6540(4) 0.6570(2) 0.0822(13) Uani 1 1 d . . . . .
H44 H 0.7981 0.6061 0.6172 0.099 Uiso 1 1 calc R U . . .
C45 C 0.7369(4) 0.6441(3) 0.71415(19) 0.0704(11) Uani 1 1 d . . . . .
H45 H 0.6754 0.5896 0.7122 0.084 Uiso 1 1 calc R U . . .
C46 C 0.7215(3) 0.6005(2) 0.91137(16) 0.0413(7) Uani 1 1 d . . . . .
C47 C 0.8059(3) 0.5394(3) 0.87744(19) 0.0572(9) Uani 1 1 d . . . . .
H47 H 0.8298 0.5446 0.8336 0.069 Uiso 1 1 calc R U . . .
C48 C 0.8548(4) 0.4706(3) 0.9083(2) 0.0730(11) Uani 1 1 d . . . . .
H48 H 0.9112 0.4295 0.8850 0.088 Uiso 1 1 calc R U . . .
C49 C 0.8210(4) 0.4627(3) 0.9724(2) 0.0754(11) Uani 1 1 d . . . . .
H49 H 0.8538 0.4159 0.9928 0.090 Uiso 1 1 calc R U . . .
C50 C 0.7393(5) 0.5228(3) 1.0069(2) 0.0749(12) Uani 1 1 d . . . . .
H50 H 0.7176 0.5178 1.0511 0.090 Uiso 1 1 calc R U . . .
C51 C 0.6888(4) 0.5909(2) 0.97661(19) 0.0576(9) Uani 1 1 d . . . . .
H51 H 0.6318 0.6312 1.0003 0.069 Uiso 1 1 calc R U . . .
C52 C 0.4240(3) 0.6786(2) 0.82845(16) 0.0416(7) Uani 1 1 d . . . . .
C53 C 0.3753(3) 0.6855(3) 0.76253(18) 0.0555(9) Uani 1 1 d . . . . .
H53 H 0.4382 0.7037 0.7329 0.067 Uiso 1 1 calc R U . . .
C54 C 0.2341(4) 0.6657(3) 0.7398(2) 0.0675(10) Uani 1 1 d . . . . .
H54 H 0.2027 0.6711 0.6953 0.081 Uiso 1 1 calc R U . . .
C55 C 0.1413(4) 0.6381(3) 0.7825(2) 0.0673(11) Uani 1 1 d . . . . .
H55 H 0.0466 0.6239 0.7671 0.081 Uiso 1 1 calc R U . . .
C56 C 0.1875(4) 0.6314(3) 0.8487(2) 0.0673(10) Uani 1 1 d . . . . .
H56 H 0.1237 0.6131 0.8779 0.081 Uiso 1 1 calc R U . . .
C57 C 0.3274(3) 0.6515(2) 0.87168(19) 0.0524(8) Uani 1 1 d . . . . .
H57 H 0.3577 0.6469 0.9165 0.063 Uiso 1 1 calc R U . . .
C58 C 0.7224(3) 0.6869(2) 0.25848(16) 0.0476(8) Uani 1 1 d . . . . .
C59 C 0.7019(4) 0.7740(3) 0.2454(2) 0.0627(10) Uani 1 1 d . . . . .
H59 H 0.7484 0.8285 0.2747 0.075 Uiso 1 1 calc R U . . .
C60 C 0.6131(4) 0.7814(3) 0.1893(2) 0.0699(11) Uani 1 1 d . . . . .
H60 H 0.6011 0.8409 0.1811 0.084 Uiso 1 1 calc R U . . .
C61 C 0.5434(4) 0.7034(3) 0.14606(19) 0.0669(11) Uani 1 1 d . . . . .
H61 H 0.4837 0.7089 0.1084 0.080 Uiso 1 1 calc R U . . .
C62 C 0.5616(4) 0.6161(3) 0.15836(19) 0.0689(11) Uani 1 1 d . . . . .
H62 H 0.5133 0.5622 0.1291 0.083 Uiso 1 1 calc R U . . .
C63 C 0.6515(4) 0.6073(3) 0.21419(18) 0.0614(9) Uani 1 1 d . . . . .
H63 H 0.6639 0.5476 0.2217 0.074 Uiso 1 1 calc R U . . .
C64 C 1.0682(3) 0.6894(2) 0.33050(18) 0.0522(8) Uani 1 1 d . . . . .
C65 C 1.1734(4) 0.6864(3) 0.3813(2) 0.0762(12) Uani 1 1 d . . . . .
H65 H 1.1509 0.6793 0.4250 0.091 Uiso 1 1 calc R U . . .
C66 C 1.3121(4) 0.6938(4) 0.3672(3) 0.0973(16) Uani 1 1 d . . . . .
H66 H 1.3822 0.6901 0.4010 0.117 Uiso 1 1 calc R U . . .
C67 C 1.3457(4) 0.7067(4) 0.3038(3) 0.0937(16) Uani 1 1 d . . . . .
H67 H 1.4387 0.7117 0.2945 0.112 Uiso 1 1 calc R U . . .
C68 C 1.2438(5) 0.7123(4) 0.2542(2) 0.0876(14) Uani 1 1 d . . . . .
H68 H 1.2676 0.7225 0.2114 0.105 Uiso 1 1 calc R U . . .
C69 C 1.1051(4) 0.7029(3) 0.2669(2) 0.0695(11) Uani 1 1 d . . . . .
H69 H 1.0359 0.7057 0.2323 0.083 Uiso 1 1 calc R U . . .
C70 C 0.7784(4) 0.5637(3) 0.39250(18) 0.0580(9) Uani 1 1 d . . . . .
C71 C 0.6391(5) 0.5388(3) 0.3929(2) 0.0846(13) Uani 1 1 d . . . . .
H71 H 0.5754 0.5702 0.3718 0.101 Uiso 1 1 calc R U . . .
C72 C 0.5909(6) 0.4653(4) 0.4253(3) 0.1094(18) Uani 1 1 d . . . . .
H72 H 0.4954 0.4487 0.4259 0.131 Uiso 1 1 calc R U . . .
C73 C 0.6839(8) 0.4189(4) 0.4554(3) 0.114(2) Uani 1 1 d . . . . .
H73 H 0.6522 0.3729 0.4791 0.137 Uiso 1 1 calc R U . . .
C74 C 0.8224(7) 0.4389(4) 0.4513(3) 0.118(2) Uani 1 1 d . . . . .
H74 H 0.8855 0.4043 0.4696 0.141 Uiso 1 1 calc R U . . .
C75 C 0.8692(5) 0.5109(3) 0.4200(3) 0.0909(14) Uani 1 1 d . . . . .
H75 H 0.9646 0.5244 0.4173 0.109 Uiso 1 1 calc R U . . .
N1 N 0.3663(3) 0.9247(2) 1.11877(15) 0.0536(7) Uani 1 1 d . . . . .
N2 N 1.1599(3) 0.9407(2) 0.63841(17) 0.0690(9) Uani 1 1 d . . . . .
O1 O 0.7114(2) 0.83649(15) 0.91805(11) 0.0511(5) Uani 1 1 d . . . . .
O2 O 0.5598(2) 0.77873(15) 0.98091(11) 0.0510(5) Uani 1 1 d . . . . .
O3 O 0.8061(2) 0.80031(17) 0.40680(12) 0.0605(6) Uani 1 1 d . . . . .
O4 O 0.9539(3) 0.76167(18) 0.48316(12) 0.0618(6) Uani 1 1 d . . . . .
Sn1 Sn 0.64186(2) 0.70162(2) 0.85996(2) 0.04064(7) Uani 1 1 d . . . . .
Sn2 Sn 0.85402(2) 0.67687(2) 0.34733(2) 0.05032(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 O2 1.229(4) . ?
C1 O1 1.300(4) . ?
C1 C2 1.483(4) . ?
C2 C3 1.390(4) . ?
C2 C7 1.412(4) . ?
C3 C4 1.377(5) . ?
C4 C5 1.365(5) . ?
C5 C6 1.375(5) . ?
C6 C7 1.387(4) . ?
C7 C8 1.479(4) . ?
C8 N1 1.256(4) . ?
C9 C10 1.372(5) . ?
C9 C14 1.381(5) . ?
C9 N1 1.429(4) . ?
C10 C11 1.385(5) . ?
C11 C12 1.354(6) . ?
C12 C13 1.360(6) . ?
C13 C14 1.377(6) . ?
C21 O4 1.227(4) . ?
C21 O3 1.294(4) . ?
C21 C22 1.499(5) . ?
C22 C27 1.385(5) . ?
C22 C23 1.396(5) . ?
C23 C24 1.376(5) . ?
C24 C25 1.384(6) . ?
C25 C26 1.355(5) . ?
C26 C27 1.398(5) . ?
C27 C28 1.469(5) . ?
C28 N2 1.256(4) . ?
C29 C30 1.349(6) . ?
C29 C34 1.371(6) . ?
C29 N2 1.426(5) . ?
C30 C31 1.383(7) . ?
C31 C32 1.313(7) . ?
C32 C33 1.343(7) . ?
C33 C34 1.376(6) . ?
C40 C45 1.377(5) . ?
C40 C41 1.389(5) . ?
C40 Sn1 2.139(3) . ?
C41 C42 1.381(5) . ?
C42 C43 1.349(6) . ?
C43 C44 1.356(6) . ?
C44 C45 1.406(5) . ?
C46 C47 1.381(4) . ?
C46 C51 1.382(4) . ?
C46 Sn1 2.129(3) . ?
C47 C48 1.382(5) . ?
C48 C49 1.358(6) . ?
C49 C50 1.358(5) . ?
C50 C51 1.373(5) . ?
C52 C53 1.380(4) . ?
C52 C57 1.392(4) . ?
C52 Sn1 2.121(3) . ?
C53 C54 1.384(5) . ?
C54 C55 1.362(5) . ?
C55 C56 1.377(5) . ?
C56 C57 1.374(5) . ?
C58 C59 1.377(5) . ?
C58 C63 1.380(5) . ?
C58 Sn2 2.130(3) . ?
C59 C60 1.381(5) . ?
C60 C61 1.352(5) . ?
C61 C62 1.368(6) . ?
C62 C63 1.389(5) . ?
C64 C69 1.379(5) . ?
C64 C65 1.386(5) . ?
C64 Sn2 2.115(3) . ?
C65 C66 1.387(5) . ?
C66 C67 1.362(6) . ?
C67 C68 1.358(6) . ?
C68 C69 1.380(5) . ?
C70 C71 1.357(5) . ?
C70 C75 1.379(6) . ?
C70 Sn2 2.117(4) . ?
C71 C72 1.409(7) . ?
C72 C73 1.356(8) . ?
C73 C74 1.350(8) . ?
C74 C75 1.376(6) . ?
O1 Sn1 2.076(2) . ?
O3 Sn2 2.058(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 120.7(3) . . ?
O2 C1 C2 122.4(3) . . ?
O1 C1 C2 117.0(3) . . ?
C3 C2 C7 119.5(3) . . ?
C3 C2 C1 118.8(3) . . ?
C7 C2 C1 121.7(3) . . ?
C4 C3 C2 120.3(3) . . ?
C5 C4 C3 120.2(3) . . ?
C4 C5 C6 120.6(3) . . ?
C5 C6 C7 120.9(3) . . ?
C6 C7 C2 118.4(3) . . ?
C6 C7 C8 119.3(3) . . ?
C2 C7 C8 122.1(3) . . ?
N1 C8 C7 121.1(3) . . ?
C10 C9 C14 118.5(3) . . ?
C10 C9 N1 124.6(3) . . ?
C14 C9 N1 116.9(3) . . ?
C9 C10 C11 120.4(4) . . ?
C12 C11 C10 120.5(4) . . ?
C11 C12 C13 119.5(4) . . ?
C12 C13 C14 120.8(4) . . ?
C13 C14 C9 120.2(4) . . ?
O4 C21 O3 121.4(3) . . ?
O4 C21 C22 123.0(3) . . ?
O3 C21 C22 115.6(3) . . ?
C27 C22 C23 120.1(3) . . ?
C27 C22 C21 121.5(3) . . ?
C23 C22 C21 118.4(3) . . ?
C24 C23 C22 120.0(4) . . ?
C23 C24 C25 120.0(4) . . ?
C26 C25 C24 120.0(4) . . ?
C25 C26 C27 121.6(4) . . ?
C22 C27 C26 118.3(3) . . ?
C22 C27 C28 122.2(3) . . ?
C26 C27 C28 119.3(3) . . ?
N2 C28 C27 121.9(3) . . ?
C30 C29 C34 117.3(4) . . ?
C30 C29 N2 117.5(4) . . ?
C34 C29 N2 125.2(4) . . ?
C29 C30 C31 120.8(5) . . ?
C32 C31 C30 121.4(5) . . ?
C31 C32 C33 119.2(5) . . ?
C32 C33 C34 120.7(6) . . ?
C29 C34 C33 120.5(5) . . ?
C45 C40 C41 117.9(3) . . ?
C45 C40 Sn1 120.4(3) . . ?
C41 C40 Sn1 121.7(2) . . ?
C42 C41 C40 121.2(4) . . ?
C43 C42 C41 120.1(4) . . ?
C42 C43 C44 120.6(4) . . ?
C43 C44 C45 120.2(4) . . ?
C40 C45 C44 120.0(4) . . ?
C47 C46 C51 118.1(3) . . ?
C47 C46 Sn1 118.9(2) . . ?
C51 C46 Sn1 122.9(2) . . ?
C46 C47 C48 120.3(3) . . ?
C49 C48 C47 120.3(4) . . ?
C48 C49 C50 120.2(4) . . ?
C49 C50 C51 120.1(4) . . ?
C50 C51 C46 120.9(3) . . ?
C53 C52 C57 118.3(3) . . ?
C53 C52 Sn1 120.2(2) . . ?
C57 C52 Sn1 121.5(2) . . ?
C52 C53 C54 121.0(3) . . ?
C55 C54 C53 119.9(4) . . ?
C54 C55 C56 120.1(3) . . ?
C57 C56 C55 120.3(3) . . ?
C56 C57 C52 120.5(3) . . ?
C59 C58 C63 118.2(3) . . ?
C59 C58 Sn2 120.3(3) . . ?
C63 C58 Sn2 121.4(3) . . ?
C58 C59 C60 120.8(4) . . ?
C61 C60 C59 120.9(4) . . ?
C60 C61 C62 119.3(4) . . ?
C61 C62 C63 120.7(4) . . ?
C58 C63 C62 120.2(4) . . ?
C69 C64 C65 118.5(3) . . ?
C69 C64 Sn2 118.8(3) . . ?
C65 C64 Sn2 122.6(3) . . ?
C64 C65 C66 120.2(4) . . ?
C67 C66 C65 120.0(4) . . ?
C68 C67 C66 120.3(4) . . ?
C67 C68 C69 120.4(4) . . ?
C64 C69 C68 120.5(4) . . ?
C71 C70 C75 118.1(4) . . ?
C71 C70 Sn2 120.9(3) . . ?
C75 C70 Sn2 120.9(3) . . ?
C70 C71 C72 120.1(5) . . ?
C73 C72 C71 119.9(5) . . ?
C74 C73 C72 120.4(5) . . ?
C73 C74 C75 119.5(5) . . ?
C74 C75 C70 121.8(5) . . ?
C8 N1 C9 119.8(3) . . ?
C28 N2 C29 119.2(3) . . ?
C1 O1 Sn1 105.24(18) . . ?
C21 O3 Sn2 109.6(2) . . ?
O1 Sn1 C52 113.73(10) . . ?
O1 Sn1 C46 109.05(10) . . ?
C52 Sn1 C46 116.19(11) . . ?
O1 Sn1 C40 96.13(11) . . ?
C52 Sn1 C40 109.74(12) . . ?
C46 Sn1 C40 110.18(12) . . ?
O3 Sn2 C64 110.68(12) . . ?
O3 Sn2 C70 108.04(12) . . ?
C64 Sn2 C70 116.88(14) . . ?
O3 Sn2 C58 93.95(11) . . ?
C64 Sn2 C58 112.33(12) . . ?
C70 Sn2 C58 112.49(13) . . ?

_refine_diff_density_max         0.698
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_Compound8
_database_code_depnum_ccdc_archive 'CCDC 1533449'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-12-19 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         'C34 H30 N2 O2 Sn'
_chemical_formula_sum            'C34 H30 N2 O2 Sn'
_chemical_formula_weight         617.29

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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.7022(6)
_cell_length_b                   10.3673(6)
_cell_length_c                   48.186(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.817(4)
_cell_angle_gamma                90
_cell_volume                     5838.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5692
_cell_measurement_theta_max      25.8410
_cell_measurement_theta_min      3.9020

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             2512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.908
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84253
_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   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'CCD plate'
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_reflns_number            22687
_diffrn_reflns_av_unetI/netI     0.1377
_diffrn_reflns_av_R_equivalents  0.0965
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       64
_diffrn_reflns_theta_min         3.211
_diffrn_reflns_theta_max         29.041
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             13233
_reflns_number_gt                7477
_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_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_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)+54.8253P] 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         13233
_refine_ls_number_parameters     707
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1908
_refine_ls_R_factor_gt           0.1246
_refine_ls_wR_factor_ref         0.2311
_refine_ls_wR_factor_gt          0.2046
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.001
_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 0.8405(9) 0.5108(11) 0.6362(2) 0.051(3) Uani 1 1 d . . . . .
C2 C 0.7473(9) 0.4780(9) 0.6554(2) 0.042(2) Uani 1 1 d . . . . .
C3 C 0.6648(10) 0.3897(11) 0.6475(2) 0.054(3) Uani 1 1 d . . . . .
H3 H 0.6696 0.3446 0.6309 0.064 Uiso 1 1 calc R U . . .
C4 C 0.5740(10) 0.3682(12) 0.6644(3) 0.061(3) Uani 1 1 d . . . . .
H4 H 0.5169 0.3105 0.6585 0.073 Uiso 1 1 calc R U . . .
C5 C 0.5662(9) 0.4294(10) 0.6893(2) 0.045(2) Uani 1 1 d . . . . .
C6 C 0.6526(9) 0.5160(10) 0.6976(2) 0.046(3) Uani 1 1 d . . . . .
H6 H 0.6501 0.5580 0.7146 0.056 Uiso 1 1 calc R U . . .
C7 C 0.7428(9) 0.5398(11) 0.6803(2) 0.048(3) Uani 1 1 d . . . . .
H7 H 0.7999 0.5980 0.6858 0.058 Uiso 1 1 calc R U . . .
C8 C 0.4683(9) 0.4079(10) 0.7069(2) 0.046(3) Uani 1 1 d . . . . .
H8 H 0.4181 0.3405 0.7026 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3564(9) 0.4555(10) 0.7443(2) 0.046(3) Uani 1 1 d . . . . .
C10 C 0.2709(10) 0.3645(11) 0.7396(2) 0.055(3) Uani 1 1 d . . . . .
H10 H 0.2709 0.3132 0.7238 0.066 Uiso 1 1 calc R U . . .
C11 C 0.1856(9) 0.3492(11) 0.7582(3) 0.053(3) Uani 1 1 d . . . . .
H11 H 0.1279 0.2893 0.7544 0.064 Uiso 1 1 calc R U . . .
C12 C 0.1842(8) 0.4215(9) 0.7827(2) 0.039(2) Uani 1 1 d . . . . .
C13 C 0.2709(9) 0.5120(10) 0.7865(2) 0.044(3) Uani 1 1 d . . . . .
H13 H 0.2724 0.5632 0.8024 0.053 Uiso 1 1 calc R U . . .
C14 C 0.3536(9) 0.5287(10) 0.7681(2) 0.046(3) Uani 1 1 d . . . . .
H14 H 0.4097 0.5910 0.7715 0.055 Uiso 1 1 calc R U . . .
C15 C 0.0161(10) 0.3029(12) 0.7968(3) 0.060(3) Uani 1 1 d . . . . .
H15A H -0.0310 0.2965 0.8125 0.090 Uiso 1 1 calc R U . . .
H15B H 0.0536 0.2220 0.7940 0.090 Uiso 1 1 calc R U . . .
H15C H -0.0308 0.3241 0.7805 0.090 Uiso 1 1 calc R U . . .
C16 C 0.0983(11) 0.4838(13) 0.8256(3) 0.073(4) Uani 1 1 d . . . . .
H16A H 0.0339 0.4615 0.8362 0.109 Uiso 1 1 calc R U . . .
H16B H 0.0917 0.5722 0.8198 0.109 Uiso 1 1 calc R U . . .
H16C H 0.1676 0.4727 0.8369 0.109 Uiso 1 1 calc R U . . .
C21 C 0.2218(9) 0.6572(11) 0.8818(2) 0.045(3) Uani 1 1 d . . . . .
C22 C 0.3195(8) 0.6787(10) 0.8638(2) 0.040(2) Uani 1 1 d . . . . .
C23 C 0.3163(10) 0.7835(11) 0.8467(2) 0.049(3) Uani 1 1 d . . . . .
H23 H 0.2548 0.8403 0.8469 0.059 Uiso 1 1 calc R U . . .
C24 C 0.4049(10) 0.8057(12) 0.8291(3) 0.059(3) Uani 1 1 d . . . . .
H24 H 0.4034 0.8790 0.8180 0.071 Uiso 1 1 calc R U . . .
C25 C 0.4936(9) 0.7218(11) 0.8280(2) 0.045(3) Uani 1 1 d . . . . .
C26 C 0.4979(9) 0.6155(12) 0.8457(3) 0.057(3) Uani 1 1 d . . . . .
H26 H 0.5588 0.5580 0.8454 0.068 Uiso 1 1 calc R U . . .
C27 C 0.4107(9) 0.5955(12) 0.8639(2) 0.055(3) Uani 1 1 d . . . . .
H27 H 0.4143 0.5259 0.8761 0.066 Uiso 1 1 calc R U . . .
C28 C 0.5827(10) 0.7416(12) 0.8079(2) 0.052(3) Uani 1 1 d . . . . .
H28 H 0.5812 0.8185 0.7979 0.062 Uiso 1 1 calc R U . . .
C29 C 0.7371(9) 0.6842(11) 0.7815(2) 0.046(3) Uani 1 1 d . . . . .
C30 C 0.7232(10) 0.7775(13) 0.7615(3) 0.062(4) Uani 1 1 d . . . . .
H30 H 0.6601 0.8320 0.7616 0.075 Uiso 1 1 calc R U . . .
C31 C 0.8010(10) 0.7925(11) 0.7410(2) 0.050(3) Uani 1 1 d . . . . .
H31 H 0.7890 0.8564 0.7277 0.060 Uiso 1 1 calc R U . . .
C32 C 0.8963(9) 0.7142(10) 0.7402(2) 0.043(2) Uani 1 1 d . . . . .
C33 C 0.9090(9) 0.6196(11) 0.7607(2) 0.051(3) Uani 1 1 d . . . . .
H33 H 0.9715 0.5643 0.7607 0.061 Uiso 1 1 calc R U . . .
C34 C 0.8309(9) 0.6065(11) 0.7810(3) 0.053(3) Uani 1 1 d . . . . .
H34 H 0.8424 0.5435 0.7946 0.064 Uiso 1 1 calc R U . . .
C35 C 1.0655(11) 0.6355(13) 0.7171(3) 0.073(4) Uani 1 1 d . . . . .
H35A H 1.1019 0.6504 0.7000 0.110 Uiso 1 1 calc R U . . .
H35B H 1.0364 0.5490 0.7173 0.110 Uiso 1 1 calc R U . . .
H35C H 1.1202 0.6473 0.7324 0.110 Uiso 1 1 calc R U . . .
C36 C 0.9610(11) 0.8236(13) 0.6994(2) 0.063(3) Uani 1 1 d . . . . .
H36A H 1.0342 0.8416 0.6921 0.094 Uiso 1 1 calc R U . . .
H36B H 0.9321 0.9001 0.7078 0.094 Uiso 1 1 calc R U . . .
H36C H 0.9086 0.7961 0.6846 0.094 Uiso 1 1 calc R U . . .
C41 C 1.1422(10) 0.5777(13) 0.6142(3) 0.061(3) Uani 1 1 d . . . . .
C42 C 1.2385(10) 0.5259(13) 0.6026(3) 0.068(4) Uani 1 1 d . . . . .
H42 H 1.2301 0.4776 0.5864 0.081 Uiso 1 1 calc R U . . .
C43 C 1.3468(11) 0.5450(16) 0.6149(3) 0.080(4) Uani 1 1 d . . . . .
H43 H 1.4104 0.5087 0.6071 0.096 Uiso 1 1 calc R U . . .
C44 C 1.3594(12) 0.6176(16) 0.6385(3) 0.084(5) Uani 1 1 d . . . . .
H44 H 1.4322 0.6309 0.6466 0.101 Uiso 1 1 calc R U . . .
C45 C 1.2656(13) 0.6717(18) 0.6506(3) 0.102(6) Uani 1 1 d . . . . .
H45 H 1.2738 0.7202 0.6668 0.122 Uiso 1 1 calc R U . . .
C46 C 1.1567(11) 0.6503(15) 0.6372(3) 0.077(4) Uani 1 1 d . . . . .
H46 H 1.0928 0.6877 0.6447 0.093 Uiso 1 1 calc R U . . .
C47 C 1.0024(10) 0.3961(12) 0.5636(3) 0.057(3) Uani 1 1 d . . . . .
C48 C 1.0438(12) 0.4293(16) 0.5385(3) 0.084(4) Uani 1 1 d . . . . .
H48 H 1.0554 0.5160 0.5345 0.100 Uiso 1 1 calc R U . . .
C49 C 1.0690(14) 0.336(2) 0.5187(3) 0.092(5) Uani 1 1 d . . . . .
H49 H 1.0922 0.3607 0.5012 0.111 Uiso 1 1 calc R U . . .
C50 C 1.0595(14) 0.2125(19) 0.5251(4) 0.088(5) Uani 1 1 d . . . . .
H50 H 1.0769 0.1499 0.5121 0.106 Uiso 1 1 calc R U . . .
C51 C 1.0239(16) 0.1758(17) 0.5508(4) 0.113(7) Uani 1 1 d . . . . .
H51 H 1.0209 0.0890 0.5556 0.136 Uiso 1 1 calc R U . . .
C52 C 0.9928(13) 0.2692(15) 0.5691(3) 0.083(4) Uani 1 1 d . . . . .
H52 H 0.9642 0.2440 0.5860 0.099 Uiso 1 1 calc R U . . .
C53 C 0.8918(11) 0.7028(14) 0.5760(3) 0.064(4) Uani 1 1 d . . . . .
C54 C 0.8195(13) 0.6877(15) 0.5529(3) 0.078(4) Uani 1 1 d . . . . .
H54 H 0.8098 0.6058 0.5453 0.094 Uiso 1 1 calc R U . . .
C55 C 0.7598(18) 0.792(2) 0.5406(4) 0.119(7) Uani 1 1 d . . . . .
H55 H 0.7116 0.7807 0.5248 0.143 Uiso 1 1 calc R U . . .
C56 C 0.7756(19) 0.908(2) 0.5525(5) 0.115(8) Uani 1 1 d . . . . .
H56 H 0.7369 0.9782 0.5445 0.139 Uiso 1 1 calc R U . . .
C57 C 0.8432(19) 0.9284(18) 0.5750(5) 0.119(7) Uani 1 1 d . . . . .
H57 H 0.8504 1.0107 0.5825 0.143 Uiso 1 1 calc R U . . .
C58 C 0.9028(14) 0.8263(16) 0.5871(4) 0.094(5) Uani 1 1 d . . . . .
H58 H 0.9506 0.8402 0.6028 0.112 Uiso 1 1 calc R U . . .
C61 C 0.1599(10) 0.4297(12) 0.9537(2) 0.055(3) Uani 1 1 d . U . . .
C62 C 0.0987(13) 0.3954(15) 0.9756(3) 0.085(5) Uani 1 1 d . U . . .
H62 H 0.0259 0.4293 0.9773 0.102 Uiso 1 1 calc R U . . .
C63 C 0.1429(17) 0.3102(17) 0.9958(3) 0.102(5) Uani 1 1 d . U . . .
H63 H 0.0987 0.2867 1.0105 0.122 Uiso 1 1 calc R U . . .
C64 C 0.2480(17) 0.2621(16) 0.9941(3) 0.099(5) Uani 1 1 d . U . . .
H64 H 0.2773 0.2049 1.0075 0.119 Uiso 1 1 calc R U . . .
C65 C 0.3104(16) 0.2969(19) 0.9731(4) 0.121(6) Uani 1 1 d . U . . .
H65 H 0.3844 0.2653 0.9720 0.145 Uiso 1 1 calc R U . . .
C66 C 0.2667(13) 0.3788(17) 0.9529(3) 0.099(5) Uani 1 1 d . U . . .
H66 H 0.3117 0.4003 0.9383 0.119 Uiso 1 1 calc R U . . .
C67 C -0.0350(9) 0.4682(12) 0.8963(2) 0.053(3) Uani 1 1 d . . . . .
C68 C -0.1013(9) 0.5353(13) 0.8777(2) 0.056(3) Uani 1 1 d . . . . .
H68 H -0.0924 0.6242 0.8764 0.067 Uiso 1 1 calc R U . . .
C69 C -0.1835(10) 0.4728(17) 0.8601(3) 0.072(4) Uani 1 1 d . . . . .
H69 H -0.2271 0.5177 0.8466 0.086 Uiso 1 1 calc R U . . .
C70 C -0.1964(12) 0.3421(18) 0.8638(3) 0.082(5) Uani 1 1 d . . . . .
H70 H -0.2536 0.3000 0.8532 0.098 Uiso 1 1 calc R U . . .
C71 C -0.1320(12) 0.2730(16) 0.8816(4) 0.091(5) Uani 1 1 d . . . . .
H71 H -0.1413 0.1840 0.8825 0.109 Uiso 1 1 calc R U . . .
C72 C -0.0497(10) 0.3341(13) 0.8991(3) 0.060(3) Uani 1 1 d . . . . .
H72 H -0.0059 0.2874 0.9122 0.072 Uiso 1 1 calc R U . . .
C73 C 0.0467(11) 0.7412(12) 0.9394(3) 0.059(3) Uani 1 1 d . U . . .
C74 C 0.1191(14) 0.8111(16) 0.9555(4) 0.093(5) Uani 1 1 d . U . . .
H74 H 0.1902 0.7769 0.9610 0.111 Uiso 1 1 calc R U . . .
C75 C 0.091(2) 0.932(2) 0.9643(5) 0.130(7) Uani 1 1 d . U . . .
H75 H 0.1427 0.9791 0.9755 0.155 Uiso 1 1 calc R U . . .
C76 C -0.010(2) 0.9839(17) 0.9568(5) 0.130(8) Uani 1 1 d . U . . .
H76 H -0.0283 1.0667 0.9626 0.156 Uiso 1 1 calc R U . . .
C77 C -0.0864(19) 0.9157(18) 0.9409(4) 0.115(6) Uani 1 1 d . U . . .
H77 H -0.1575 0.9512 0.9360 0.138 Uiso 1 1 calc R U . . .
C78 C -0.0600(15) 0.7956(15) 0.9319(3) 0.091(5) Uani 1 1 d . U . . .
H78 H -0.1127 0.7495 0.9207 0.109 Uiso 1 1 calc R U . . .
N1 N 0.4506(8) 0.4770(8) 0.72735(19) 0.048(2) Uani 1 1 d . . . . .
N2 N 0.1007(8) 0.4024(9) 0.8018(2) 0.057(3) Uani 1 1 d . . . . .
N3 N 0.6604(8) 0.6625(10) 0.8032(2) 0.053(2) Uani 1 1 d . . . . .
N4 N 0.9729(8) 0.7252(10) 0.7195(2) 0.057(3) Uani 1 1 d . . . . .
O1 O 0.8561(7) 0.4390(8) 0.61518(15) 0.061(2) Uani 1 1 d . . . . .
O2 O 0.9017(7) 0.6063(8) 0.64109(18) 0.064(2) Uani 1 1 d . . . . .
O3 O 0.2404(6) 0.5746(8) 0.90182(16) 0.056(2) Uani 1 1 d . . . . .
O4 O 0.1292(6) 0.7079(8) 0.87776(17) 0.058(2) Uani 1 1 d . . . . .
Sn1 Sn 0.97949(7) 0.54194(9) 0.59416(2) 0.0536(2) Uani 1 1 d . . . . .
Sn2 Sn 0.09098(6) 0.55863(8) 0.92292(2) 0.0474(2) 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 O2 1.237(13) . ?
C1 O1 1.279(13) . ?
C1 C2 1.502(15) . ?
C2 C7 1.364(14) . ?
C2 C3 1.371(14) . ?
C3 C4 1.388(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(14) . ?
C5 C8 1.476(14) . ?
C6 C7 1.398(14) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.242(13) . ?
C8 H8 0.9300 . ?
C9 C14 1.376(14) . ?
C9 C10 1.385(15) . ?
C9 N1 1.421(13) . ?
C10 C11 1.383(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.398(14) . ?
C11 H11 0.9300 . ?
C12 N2 1.390(13) . ?
C12 C13 1.388(13) . ?
C13 C14 1.359(14) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 N2 1.442(14) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N2 1.426(14) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C21 O4 1.212(12) . ?
C21 O3 1.301(12) . ?
C21 C22 1.484(14) . ?
C22 C23 1.362(14) . ?
C22 C27 1.372(14) . ?
C23 C24 1.391(15) . ?
C23 H23 0.9300 . ?
C24 C25 1.357(15) . ?
C24 H24 0.9300 . ?
C25 C26 1.394(15) . ?
C25 C28 1.473(15) . ?
C26 C27 1.394(15) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 N3 1.253(14) . ?
C28 H28 0.9300 . ?
C29 C34 1.363(15) . ?
C29 C30 1.370(16) . ?
C29 N3 1.429(14) . ?
C30 C31 1.382(14) . ?
C30 H30 0.9300 . ?
C31 C32 1.382(15) . ?
C31 H31 0.9300 . ?
C32 N4 1.377(13) . ?
C32 C33 1.397(15) . ?
C33 C34 1.375(15) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 N4 1.437(14) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 N4 1.409(14) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C41 C46 1.344(17) . ?
C41 C42 1.390(15) . ?
C41 Sn1 2.125(13) . ?
C42 C43 1.387(16) . ?
C42 H42 0.9300 . ?
C43 C44 1.364(18) . ?
C43 H43 0.9300 . ?
C44 C45 1.387(19) . ?
C44 H44 0.9300 . ?
C45 C46 1.417(18) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 C52 1.349(18) . ?
C47 C48 1.371(17) . ?
C47 Sn1 2.136(13) . ?
C48 C49 1.400(19) . ?
C48 H48 0.9300 . ?
C49 C50 1.32(2) . ?
C49 H49 0.9300 . ?
C50 C51 1.38(2) . ?
C50 H50 0.9300 . ?
C51 C52 1.37(2) . ?
C51 H51 0.9300 . ?
C52 H52 0.9300 . ?
C53 C54 1.370(19) . ?
C53 C58 1.39(2) . ?
C53 Sn1 2.125(14) . ?
C54 C55 1.40(2) . ?
C54 H54 0.9300 . ?
C55 C56 1.35(3) . ?
C55 H55 0.9300 . ?
C56 C57 1.33(3) . ?
C56 H56 0.9300 . ?
C57 C58 1.38(2) . ?
C57 H57 0.9300 . ?
C58 H58 0.9300 . ?
C61 C62 1.355(16) . ?
C61 C66 1.358(17) . ?
C61 Sn2 2.125(12) . ?
C62 C63 1.39(2) . ?
C62 H62 0.9300 . ?
C63 C64 1.33(2) . ?
C63 H63 0.9300 . ?
C64 C65 1.33(2) . ?
C64 H64 0.9300 . ?
C65 C66 1.37(2) . ?
C65 H65 0.9300 . ?
C66 H66 0.9300 . ?
C67 C68 1.351(15) . ?
C67 C72 1.407(17) . ?
C67 Sn2 2.123(11) . ?
C68 C69 1.409(16) . ?
C68 H68 0.9300 . ?
C69 C70 1.38(2) . ?
C69 H69 0.9300 . ?
C70 C71 1.32(2) . ?
C70 H70 0.9300 . ?
C71 C72 1.399(18) . ?
C71 H71 0.9300 . ?
C72 H72 0.9300 . ?
C73 C74 1.335(19) . ?
C73 C78 1.401(19) . ?
C73 Sn2 2.127(13) . ?
C74 C75 1.37(2) . ?
C74 H74 0.9300 . ?
C75 C76 1.33(3) . ?
C75 H75 0.9300 . ?
C76 C77 1.35(3) . ?
C76 H76 0.9300 . ?
C77 C78 1.36(2) . ?
C77 H77 0.9300 . ?
C78 H78 0.9300 . ?
O1 Sn1 2.096(8) . ?
O3 Sn2 2.072(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
O2 C1 O1 120.7(11) . . ?
O2 C1 C2 119.8(11) . . ?
O1 C1 C2 119.5(10) . . ?
C7 C2 C3 120.1(10) . . ?
C7 C2 C1 119.7(10) . . ?
C3 C2 C1 120.2(10) . . ?
C2 C3 C4 119.5(10) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.8(11) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 118.0(10) . . ?
C4 C5 C8 121.5(10) . . ?
C6 C5 C8 120.4(10) . . ?
C5 C6 C7 120.2(10) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 120.3(10) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
N1 C8 C5 122.1(10) . . ?
N1 C8 H8 118.9 . . ?
C5 C8 H8 118.9 . . ?
C14 C9 C10 117.7(10) . . ?
C14 C9 N1 116.2(10) . . ?
C10 C9 N1 126.0(10) . . ?
C11 C10 C9 120.8(10) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 121.6(10) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
N2 C12 C13 122.7(9) . . ?
N2 C12 C11 121.4(9) . . ?
C13 C12 C11 115.9(10) . . ?
C14 C13 C12 122.6(10) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C13 C14 C9 121.5(10) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C21 O3 121.4(10) . . ?
O4 C21 C22 123.3(10) . . ?
O3 C21 C22 115.2(10) . . ?
C23 C22 C27 120.1(10) . . ?
C23 C22 C21 118.2(10) . . ?
C27 C22 C21 121.6(10) . . ?
C22 C23 C24 120.1(11) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.9(11) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 119.1(10) . . ?
C24 C25 C28 120.3(11) . . ?
C26 C25 C28 120.6(11) . . ?
C25 C26 C27 119.9(11) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C22 C27 C26 119.8(11) . . ?
C22 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
N3 C28 C25 124.8(11) . . ?
N3 C28 H28 117.6 . . ?
C25 C28 H28 117.6 . . ?
C34 C29 C30 118.2(11) . . ?
C34 C29 N3 117.1(11) . . ?
C30 C29 N3 124.7(10) . . ?
C29 C30 C31 121.4(11) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
C30 C31 C32 121.1(10) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 H31 119.4 . . ?
N4 C32 C31 121.9(10) . . ?
N4 C32 C33 121.4(10) . . ?
C31 C32 C33 116.6(10) . . ?
C34 C33 C32 121.4(11) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C29 C34 C33 121.2(11) . . ?
C29 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
N4 C35 H35A 109.5 . . ?
N4 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N4 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N4 C36 H36A 109.5 . . ?
N4 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N4 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C46 C41 C42 118.4(12) . . ?
C46 C41 Sn1 123.1(10) . . ?
C42 C41 Sn1 118.4(10) . . ?
C43 C42 C41 121.0(13) . . ?
C43 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
C44 C43 C42 119.6(13) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C43 C44 C45 121.2(13) . . ?
C43 C44 H44 119.4 . . ?
C45 C44 H44 119.4 . . ?
C44 C45 C46 117.3(13) . . ?
C44 C45 H45 121.3 . . ?
C46 C45 H45 121.3 . . ?
C41 C46 C45 122.4(13) . . ?
C41 C46 H46 118.8 . . ?
C45 C46 H46 118.8 . . ?
C52 C47 C48 117.1(14) . . ?
C52 C47 Sn1 122.7(11) . . ?
C48 C47 Sn1 119.6(10) . . ?
C47 C48 C49 121.7(15) . . ?
C47 C48 H48 119.1 . . ?
C49 C48 H48 119.1 . . ?
C50 C49 C48 119.0(15) . . ?
C50 C49 H49 120.5 . . ?
C48 C49 H49 120.5 . . ?
C49 C50 C51 120.6(16) . . ?
C49 C50 H50 119.7 . . ?
C51 C50 H50 119.7 . . ?
C52 C51 C50 119.0(16) . . ?
C52 C51 H51 120.5 . . ?
C50 C51 H51 120.5 . . ?
C47 C52 C51 122.3(15) . . ?
C47 C52 H52 118.8 . . ?
C51 C52 H52 118.8 . . ?
C54 C53 C58 117.3(15) . . ?
C54 C53 Sn1 120.7(12) . . ?
C58 C53 Sn1 121.9(12) . . ?
C53 C54 C55 122.1(17) . . ?
C53 C54 H54 118.9 . . ?
C55 C54 H54 118.9 . . ?
C56 C55 C54 117(2) . . ?
C56 C55 H55 121.5 . . ?
C54 C55 H55 121.5 . . ?
C57 C56 C55 124(2) . . ?
C57 C56 H56 118.1 . . ?
C55 C56 H56 118.1 . . ?
C56 C57 C58 119(2) . . ?
C56 C57 H57 120.3 . . ?
C58 C57 H57 120.3 . . ?
C57 C58 C53 120.5(18) . . ?
C57 C58 H58 119.8 . . ?
C53 C58 H58 119.8 . . ?
C62 C61 C66 116.1(13) . . ?
C62 C61 Sn2 120.9(10) . . ?
C66 C61 Sn2 123.0(10) . . ?
C61 C62 C63 121.3(14) . . ?
C61 C62 H62 119.4 . . ?
C63 C62 H62 119.4 . . ?
C64 C63 C62 120.5(15) . . ?
C64 C63 H63 119.8 . . ?
C62 C63 H63 119.8 . . ?
C65 C64 C63 119.1(16) . . ?
C65 C64 H64 120.4 . . ?
C63 C64 H64 120.4 . . ?
C64 C65 C66 120.6(18) . . ?
C64 C65 H65 119.7 . . ?
C66 C65 H65 119.7 . . ?
C61 C66 C65 122.4(16) . . ?
C61 C66 H66 118.8 . . ?
C65 C66 H66 118.8 . . ?
C68 C67 C72 120.1(12) . . ?
C68 C67 Sn2 122.2(10) . . ?
C72 C67 Sn2 117.7(10) . . ?
C67 C68 C69 121.1(13) . . ?
C67 C68 H68 119.5 . . ?
C69 C68 H68 119.5 . . ?
C70 C69 C68 116.8(14) . . ?
C70 C69 H69 121.6 . . ?
C68 C69 H69 121.6 . . ?
C71 C70 C69 123.7(15) . . ?
C71 C70 H70 118.2 . . ?
C69 C70 H70 118.2 . . ?
C70 C71 C72 119.8(15) . . ?
C70 C71 H71 120.1 . . ?
C72 C71 H71 120.1 . . ?
C71 C72 C67 118.4(13) . . ?
C71 C72 H72 120.8 . . ?
C67 C72 H72 120.8 . . ?
C74 C73 C78 117.7(14) . . ?
C74 C73 Sn2 122.7(11) . . ?
C78 C73 Sn2 119.5(11) . . ?
C73 C74 C75 121.3(18) . . ?
C73 C74 H74 119.3 . . ?
C75 C74 H74 119.3 . . ?
C76 C75 C74 121(2) . . ?
C76 C75 H75 119.7 . . ?
C74 C75 H75 119.7 . . ?
C75 C76 C77 119.8(19) . . ?
C75 C76 H76 120.1 . . ?
C77 C76 H76 120.1 . . ?
C76 C77 C78 121(2) . . ?
C76 C77 H77 119.7 . . ?
C78 C77 H77 119.7 . . ?
C77 C78 C73 120.0(18) . . ?
C77 C78 H78 120.0 . . ?
C73 C78 H78 120.0 . . ?
C8 N1 C9 121.9(10) . . ?
C12 N2 C16 119.5(9) . . ?
C12 N2 C15 119.3(10) . . ?
C16 N2 C15 121.2(10) . . ?
C28 N3 C29 121.0(11) . . ?
C32 N4 C36 120.8(10) . . ?
C32 N4 C35 121.7(10) . . ?
C36 N4 C35 117.6(10) . . ?
C1 O1 Sn1 102.5(7) . . ?
C21 O3 Sn2 107.6(7) . . ?
O1 Sn1 C41 119.5(4) . . ?
O1 Sn1 C53 105.6(4) . . ?
C41 Sn1 C53 117.0(5) . . ?
O1 Sn1 C47 94.9(4) . . ?
C41 Sn1 C47 107.3(5) . . ?
C53 Sn1 C47 110.2(5) . . ?
O3 Sn2 C61 95.2(4) . . ?
O3 Sn2 C67 108.5(4) . . ?
C61 Sn2 C67 111.8(5) . . ?
O3 Sn2 C73 109.8(4) . . ?
C61 Sn2 C73 113.0(5) . . ?
C67 Sn2 C73 116.3(5) . . ?

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
O2 C1 C2 C7 -10.9(15) . . . . ?
O1 C1 C2 C7 168.6(10) . . . . ?
O2 C1 C2 C3 166.7(10) . . . . ?
O1 C1 C2 C3 -13.8(15) . . . . ?
C7 C2 C3 C4 2.9(17) . . . . ?
C1 C2 C3 C4 -174.7(11) . . . . ?
C2 C3 C4 C5 -2.3(19) . . . . ?
C3 C4 C5 C6 0.3(18) . . . . ?
C3 C4 C5 C8 178.8(11) . . . . ?
C4 C5 C6 C7 1.0(16) . . . . ?
C8 C5 C6 C7 -177.5(10) . . . . ?
C3 C2 C7 C6 -1.6(16) . . . . ?
C1 C2 C7 C6 176.0(9) . . . . ?
C5 C6 C7 C2 -0.4(16) . . . . ?
C4 C5 C8 N1 -168.4(11) . . . . ?
C6 C5 C8 N1 10.0(16) . . . . ?
C14 C9 C10 C11 0.4(17) . . . . ?
N1 C9 C10 C11 177.5(11) . . . . ?
C9 C10 C11 C12 -1.9(19) . . . . ?
C10 C11 C12 N2 -177.6(11) . . . . ?
C10 C11 C12 C13 2.1(17) . . . . ?
N2 C12 C13 C14 178.7(10) . . . . ?
C11 C12 C13 C14 -1.0(15) . . . . ?
C12 C13 C14 C9 -0.4(16) . . . . ?
C10 C9 C14 C13 0.7(16) . . . . ?
N1 C9 C14 C13 -176.7(9) . . . . ?
O4 C21 C22 C23 17.9(16) . . . . ?
O3 C21 C22 C23 -165.1(10) . . . . ?
O4 C21 C22 C27 -161.5(11) . . . . ?
O3 C21 C22 C27 15.4(15) . . . . ?
C27 C22 C23 C24 0.8(17) . . . . ?
C21 C22 C23 C24 -178.7(10) . . . . ?
C22 C23 C24 C25 2.1(18) . . . . ?
C23 C24 C25 C26 -3.1(18) . . . . ?
C23 C24 C25 C28 175.7(11) . . . . ?
C24 C25 C26 C27 1.1(17) . . . . ?
C28 C25 C26 C27 -177.6(10) . . . . ?
C23 C22 C27 C26 -2.6(17) . . . . ?
C21 C22 C27 C26 176.8(10) . . . . ?
C25 C26 C27 C22 1.7(18) . . . . ?
C24 C25 C28 N3 -171.8(11) . . . . ?
C26 C25 C28 N3 6.9(17) . . . . ?
C34 C29 C30 C31 0.7(18) . . . . ?
N3 C29 C30 C31 -179.8(11) . . . . ?
C29 C30 C31 C32 -0.4(18) . . . . ?
C30 C31 C32 N4 178.0(11) . . . . ?
C30 C31 C32 C33 0.4(16) . . . . ?
N4 C32 C33 C34 -178.4(11) . . . . ?
C31 C32 C33 C34 -0.7(16) . . . . ?
C30 C29 C34 C33 -1.0(17) . . . . ?
N3 C29 C34 C33 179.5(10) . . . . ?
C32 C33 C34 C29 1.0(18) . . . . ?
C46 C41 C42 C43 2(2) . . . . ?
Sn1 C41 C42 C43 -179.5(12) . . . . ?
C41 C42 C43 C44 -1(2) . . . . ?
C42 C43 C44 C45 1(3) . . . . ?
C43 C44 C45 C46 -1(3) . . . . ?
C42 C41 C46 C45 -2(2) . . . . ?
Sn1 C41 C46 C45 179.1(13) . . . . ?
C44 C45 C46 C41 2(3) . . . . ?
C52 C47 C48 C49 4(2) . . . . ?
Sn1 C47 C48 C49 174.7(12) . . . . ?
C47 C48 C49 C50 -4(3) . . . . ?
C48 C49 C50 C51 1(3) . . . . ?
C49 C50 C51 C52 3(3) . . . . ?
C48 C47 C52 C51 1(2) . . . . ?
Sn1 C47 C52 C51 -170.2(14) . . . . ?
C50 C51 C52 C47 -4(3) . . . . ?
C58 C53 C54 C55 1(2) . . . . ?
Sn1 C53 C54 C55 179.6(12) . . . . ?
C53 C54 C55 C56 -1(3) . . . . ?
C54 C55 C56 C57 0(3) . . . . ?
C55 C56 C57 C58 1(3) . . . . ?
C56 C57 C58 C53 0(3) . . . . ?
C54 C53 C58 C57 0(2) . . . . ?
Sn1 C53 C58 C57 -179.0(13) . . . . ?
C66 C61 C62 C63 -2(2) . . . . ?
Sn2 C61 C62 C63 179.5(13) . . . . ?
C61 C62 C63 C64 1(3) . . . . ?
C62 C63 C64 C65 0(3) . . . . ?
C63 C64 C65 C66 -1(3) . . . . ?
C62 C61 C66 C65 0(3) . . . . ?
Sn2 C61 C66 C65 179.3(15) . . . . ?
C64 C65 C66 C61 1(3) . . . . ?
C72 C67 C68 C69 -1.9(17) . . . . ?
Sn2 C67 C68 C69 179.4(8) . . . . ?
C67 C68 C69 C70 2.9(18) . . . . ?
C68 C69 C70 C71 -4(2) . . . . ?
C69 C70 C71 C72 4(3) . . . . ?
C70 C71 C72 C67 -3(2) . . . . ?
C68 C67 C72 C71 1.6(18) . . . . ?
Sn2 C67 C72 C71 -179.6(10) . . . . ?
C78 C73 C74 C75 -1(2) . . . . ?
Sn2 C73 C74 C75 175.4(14) . . . . ?
C73 C74 C75 C76 0(3) . . . . ?
C74 C75 C76 C77 1(4) . . . . ?
C75 C76 C77 C78 -1(3) . . . . ?
C76 C77 C78 C73 1(3) . . . . ?
C74 C73 C78 C77 0(2) . . . . ?
Sn2 C73 C78 C77 -175.8(12) . . . . ?
C5 C8 N1 C9 -179.7(9) . . . . ?
C14 C9 N1 C8 172.7(10) . . . . ?
C10 C9 N1 C8 -4.4(17) . . . . ?
C13 C12 N2 C16 4.2(16) . . . . ?
C11 C12 N2 C16 -176.1(11) . . . . ?
C13 C12 N2 C15 -177.6(10) . . . . ?
C11 C12 N2 C15 2.1(16) . . . . ?
C25 C28 N3 C29 174.1(10) . . . . ?
C34 C29 N3 C28 168.5(11) . . . . ?
C30 C29 N3 C28 -10.9(17) . . . . ?
C31 C32 N4 C36 4.4(16) . . . . ?
C33 C32 N4 C36 -178.0(10) . . . . ?
C31 C32 N4 C35 -173.8(11) . . . . ?
C33 C32 N4 C35 3.7(17) . . . . ?
O2 C1 O1 Sn1 -7.2(12) . . . . ?
C2 C1 O1 Sn1 173.4(8) . . . . ?
O4 C21 O3 Sn2 -1.4(13) . . . . ?
C22 C21 O3 Sn2 -178.5(7) . . . . ?

_refine_diff_density_max         0.917
_refine_diff_density_min         -2.682
_refine_diff_density_rms         0.110

####################################################################### 
# 
# 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_Compound7
_database_code_depnum_ccdc_archive 'CCDC 1533448'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-12-19 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         'C32 H24 F N O2 Sn'
_chemical_formula_sum            'C32 H24 F N O2 Sn'
_chemical_formula_weight         592.21

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   19.5733(7)
_cell_length_b                   14.9548(5)
_cell_length_c                   18.3132(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5360.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6663
_cell_measurement_theta_max      28.6750
_cell_measurement_theta_min      3.7590

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             2384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.989
_shelx_estimated_absorpt_T_min   0.762
_shelx_estimated_absorpt_T_max   0.819
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88740
_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   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_reflns_number            14398
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.407
_diffrn_reflns_theta_max         29.021
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8091
_reflns_number_gt                6716
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_max     0.875
_reflns_Friedel_fraction_full    0.996

_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_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_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0269P)²+2.5108P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8091
_refine_ls_number_parameters     668
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_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 0.2106(3) 0.6109(4) 0.3688(3) 0.0454(14) Uani 1 1 d . . . . .
C2 C 0.2583(3) 0.6766(4) 0.4034(3) 0.0415(13) Uani 1 1 d . . . . .
C3 C 0.3227(3) 0.6904(4) 0.3726(3) 0.0484(14) Uani 1 1 d . . . . .
H3 H 0.3362 0.6573 0.3321 0.058 Uiso 1 1 calc R U . . .
C4 C 0.3663(3) 0.7531(4) 0.4020(3) 0.0519(15) Uani 1 1 d . . . . .
H4 H 0.4092 0.7617 0.3815 0.062 Uiso 1 1 calc R U . . .
C5 C 0.3467(3) 0.8039(4) 0.4624(3) 0.0483(14) Uani 1 1 d . . . . .
C6 C 0.2830(4) 0.7889(4) 0.4937(4) 0.0591(18) Uani 1 1 d . . . . .
H6 H 0.2697 0.8221 0.5342 0.071 Uiso 1 1 calc R U . . .
C7 C 0.2396(4) 0.7256(4) 0.4653(4) 0.0551(17) Uani 1 1 d . . . . .
H7 H 0.1976 0.7153 0.4874 0.066 Uiso 1 1 calc R U . . .
C8 C 0.3891(4) 0.8773(4) 0.4902(4) 0.0595(17) Uani 1 1 d . . . . .
H8 H 0.3741 0.9083 0.5312 0.071 Uiso 1 1 calc R U . . .
C9 C 0.4813(4) 0.9764(4) 0.4888(4) 0.0592(17) Uani 1 1 d . . . . .
C10 C 0.5233(4) 1.0229(5) 0.4418(5) 0.071(2) Uani 1 1 d . . . . .
H10 H 0.5293 1.0019 0.3944 0.085 Uiso 1 1 calc R U . . .
C11 C 0.5566(4) 1.0993(5) 0.4632(5) 0.076(2) Uani 1 1 d . . . . .
H11 H 0.5834 1.1306 0.4299 0.092 Uiso 1 1 calc R U . . .
C12 C 0.5505(4) 1.1285(5) 0.5312(4) 0.0662(19) Uani 1 1 d . . . . .
C13 C 0.5125(4) 1.0848(6) 0.5805(4) 0.085(2) Uani 1 1 d . . . . .
H13 H 0.5099 1.1051 0.6284 0.102 Uiso 1 1 calc R U . . .
C14 C 0.4765(4) 1.0074(6) 0.5588(4) 0.081(2) Uani 1 1 d . . . . .
H14 H 0.4493 0.9773 0.5924 0.097 Uiso 1 1 calc R U . . .
C16 C 0.1097(3) 0.3983(3) 0.3750(3) 0.0448(14) Uani 1 1 d . . . . .
C17 C 0.1719(4) 0.3572(4) 0.3620(4) 0.0565(17) Uani 1 1 d . . . . .
H17 H 0.2043 0.3850 0.3326 0.068 Uiso 1 1 calc R U . . .
C18 C 0.1860(4) 0.2742(4) 0.3928(4) 0.070(2) Uani 1 1 d . . . . .
H18 H 0.2278 0.2467 0.3838 0.085 Uiso 1 1 calc R U . . .
C19 C 0.1385(6) 0.2327(5) 0.4365(5) 0.084(3) Uani 1 1 d . . . . .
H19 H 0.1485 0.1777 0.4576 0.101 Uiso 1 1 calc R U . . .
C20 C 0.0760(5) 0.2727(5) 0.4493(5) 0.074(2) Uani 1 1 d . . . . .
H20 H 0.0436 0.2446 0.4784 0.089 Uiso 1 1 calc R U . . .
C21 C 0.0624(4) 0.3553(4) 0.4181(4) 0.0634(19) Uani 1 1 d . . . . .
H21 H 0.0203 0.3822 0.4264 0.076 Uiso 1 1 calc R U . . .
C22 C -0.0069(3) 0.5767(4) 0.3821(3) 0.0432(13) Uani 1 1 d . . . . .
C23 C -0.0686(3) 0.5308(4) 0.3755(4) 0.0572(16) Uani 1 1 d . . . . .
H23 H -0.0696 0.4763 0.3509 0.069 Uiso 1 1 calc R U . . .
C24 C -0.1279(4) 0.5645(6) 0.4047(5) 0.072(2) Uani 1 1 d . . . . .
H24 H -0.1689 0.5344 0.3976 0.087 Uiso 1 1 calc R U . . .
C25 C -0.1270(4) 0.6414(6) 0.4436(4) 0.077(2) Uani 1 1 d . . . . .
H25 H -0.1672 0.6632 0.4640 0.092 Uiso 1 1 calc R U . . .
C26 C -0.0670(4) 0.6874(6) 0.4532(5) 0.085(3) Uani 1 1 d . . . . .
H26 H -0.0665 0.7407 0.4795 0.102 Uiso 1 1 calc R U . . .
C27 C -0.0068(4) 0.6536(4) 0.4233(5) 0.068(2) Uani 1 1 d . . . . .
H27 H 0.0341 0.6836 0.4314 0.081 Uiso 1 1 calc R U . . .
C28 C 0.0875(3) 0.5536(4) 0.2220(4) 0.0416(14) Uani 1 1 d . . . . .
C29 C 0.1408(3) 0.5264(4) 0.1770(4) 0.0511(15) Uani 1 1 d . . . . .
H29 H 0.1783 0.4971 0.1970 0.061 Uiso 1 1 calc R U . . .
C30 C 0.1383(4) 0.5427(5) 0.1017(4) 0.068(2) Uani 1 1 d . . . . .
H30 H 0.1745 0.5249 0.0722 0.082 Uiso 1 1 calc R U . . .
C31 C 0.0835(5) 0.5845(5) 0.0715(5) 0.074(2) Uani 1 1 d . . . . .
H31 H 0.0821 0.5952 0.0215 0.088 Uiso 1 1 calc R U . . .
C32 C 0.0299(4) 0.6109(4) 0.1153(4) 0.070(2) Uani 1 1 d . . . . .
H32 H -0.0078 0.6392 0.0947 0.084 Uiso 1 1 calc R U . . .
C33 C 0.0320(3) 0.5956(4) 0.1892(4) 0.0547(16) Uani 1 1 d . . . . .
H33 H -0.0046 0.6138 0.2181 0.066 Uiso 1 1 calc R U . . .
C34 C 0.1474(3) 0.1152(3) 0.2677(3) 0.0412(13) Uani 1 1 d . . . . .
C35 C 0.0993(3) 0.1836(3) 0.2383(3) 0.0366(12) Uani 1 1 d . . . . .
C36 C 0.0338(3) 0.1907(3) 0.2656(3) 0.0426(13) Uani 1 1 d . . . . .
H36 H 0.0192 0.1522 0.3023 0.051 Uiso 1 1 calc R U . . .
C37 C -0.0103(3) 0.2551(4) 0.2384(3) 0.0439(14) Uani 1 1 d . . . . .
H37 H -0.0544 0.2595 0.2570 0.053 Uiso 1 1 calc R U . . .
C38 C 0.0106(3) 0.3129(3) 0.1839(3) 0.0404(13) Uani 1 1 d . . . . .
C39 C 0.0765(3) 0.3049(4) 0.1568(4) 0.0454(14) Uani 1 1 d . . . . .
H39 H 0.0909 0.3428 0.1197 0.054 Uiso 1 1 calc R U . . .
C40 C 0.1210(3) 0.2415(4) 0.1841(3) 0.0438(14) Uani 1 1 d . . . . .
H40 H 0.1654 0.2377 0.1662 0.053 Uiso 1 1 calc R U . . .
C42 C -0.0345(3) 0.3837(3) 0.1557(3) 0.0441(14) Uani 1 1 d . . . . .
H42 H -0.0212 0.4146 0.1140 0.053 Uiso 1 1 calc R U . . .
C43 C -0.1303(3) 0.4735(3) 0.1537(3) 0.0434(13) Uani 1 1 d . . . . .
C44 C -0.1614(3) 0.5324(4) 0.2014(4) 0.0551(16) Uani 1 1 d . . . . .
H44 H -0.1572 0.5238 0.2515 0.066 Uiso 1 1 calc R U . . .
C45 C -0.1990(3) 0.6043(4) 0.1753(4) 0.0585(17) Uani 1 1 d . . . . .
H45 H -0.2182 0.6457 0.2072 0.070 Uiso 1 1 calc R U . . .
C46 C -0.2069(3) 0.6125(4) 0.1018(4) 0.0616(18) Uani 1 1 d . . . . .
C47 C -0.1798(4) 0.5530(5) 0.0537(4) 0.068(2) Uani 1 1 d . . . . .
H47 H -0.1879 0.5592 0.0040 0.082 Uiso 1 1 calc R U . . .
C48 C -0.1406(3) 0.4840(5) 0.0790(4) 0.0592(17) Uani 1 1 d . . . . .
H48 H -0.1207 0.4441 0.0463 0.071 Uiso 1 1 calc R U . . .
C49 C 0.3665(3) 0.0846(4) 0.2519(3) 0.0475(14) Uani 1 1 d . . . . .
C50 C 0.3664(4) 0.1536(5) 0.2045(5) 0.076(2) Uani 1 1 d . . . . .
H50 H 0.3248 0.1784 0.1904 0.091 Uiso 1 1 calc R U . . .
C51 C 0.4260(5) 0.1888(7) 0.1760(6) 0.105(4) Uani 1 1 d . . . . .
H51 H 0.4244 0.2346 0.1417 0.126 Uiso 1 1 calc R U . . .
C52 C 0.4873(5) 0.1553(6) 0.1990(6) 0.095(3) Uani 1 1 d . . . . .
H52 H 0.5280 0.1803 0.1824 0.114 Uiso 1 1 calc R U . . .
C53 C 0.4883(4) 0.0867(6) 0.2452(6) 0.093(3) Uani 1 1 d . . . . .
H53 H 0.5299 0.0625 0.2596 0.112 Uiso 1 1 calc R U . . .
C54 C 0.4284(3) 0.0508(5) 0.2722(5) 0.074(2) Uani 1 1 d . . . . .
H54 H 0.4303 0.0030 0.3046 0.089 Uiso 1 1 calc R U . . .
C55 C 0.2716(3) 0.0467(4) 0.4115(4) 0.0426(14) Uani 1 1 d . . . . .
C56 C 0.3211(4) 0.0992(4) 0.4449(4) 0.0574(16) Uani 1 1 d . . . . .
H56 H 0.3550 0.1260 0.4168 0.069 Uiso 1 1 calc R U . . .
C57 C 0.3203(4) 0.1118(5) 0.5189(4) 0.072(2) Uani 1 1 d . . . . .
H57 H 0.3530 0.1480 0.5409 0.087 Uiso 1 1 calc R U . . .
C58 C 0.2720(4) 0.0716(6) 0.5600(4) 0.074(3) Uani 1 1 d . . . . .
H58 H 0.2723 0.0790 0.6105 0.089 Uiso 1 1 calc R U . . .
C59 C 0.2223(5) 0.0197(5) 0.5276(4) 0.077(2) Uani 1 1 d . . . . .
H59 H 0.1887 -0.0070 0.5562 0.093 Uiso 1 1 calc R U . . .
C60 C 0.2222(4) 0.0074(5) 0.4544(4) 0.0650(18) Uani 1 1 d . . . . .
H60 H 0.1885 -0.0278 0.4330 0.078 Uiso 1 1 calc R U . . .
C61 C 0.2535(3) -0.0967(4) 0.2508(4) 0.0478(15) Uani 1 1 d . . . . .
C62 C 0.3040(4) -0.1373(4) 0.2100(4) 0.0556(17) Uani 1 1 d . . . . .
H62 H 0.3445 -0.1069 0.2008 0.067 Uiso 1 1 calc R U . . .
C63 C 0.2949(5) -0.2222(5) 0.1826(4) 0.071(2) Uani 1 1 d . . . . .
H63 H 0.3297 -0.2498 0.1563 0.085 Uiso 1 1 calc R U . . .
C64 C 0.2344(5) -0.2655(5) 0.1943(5) 0.079(2) Uani 1 1 d . . . . .
H64 H 0.2279 -0.3222 0.1745 0.094 Uiso 1 1 calc R U . . .
C65 C 0.1834(4) -0.2276(5) 0.2343(5) 0.079(2) Uani 1 1 d . . . . .
H65 H 0.1428 -0.2582 0.2426 0.095 Uiso 1 1 calc R U . . .
C66 C 0.1930(4) -0.1426(4) 0.2625(4) 0.0633(18) Uani 1 1 d . . . . .
H66 H 0.1584 -0.1160 0.2897 0.076 Uiso 1 1 calc R U . . .
O1 O 0.1468(2) 0.6180(3) 0.3901(3) 0.0539(11) Uani 1 1 d . . . . .
O2 O 0.2287(2) 0.5548(3) 0.3251(3) 0.0571(12) Uani 1 1 d . . . . .
O3 O 0.21203(19) 0.1246(3) 0.2486(2) 0.0456(10) Uani 1 1 d . . . . .
O4 O 0.1297(2) 0.0538(2) 0.3068(3) 0.0532(11) Uani 1 1 d . . . . .
F1 F 0.5825(3) 1.2041(3) 0.5508(3) 0.1019(17) Uani 1 1 d . . . . .
F2 F -0.2448(3) 0.6822(3) 0.0761(3) 0.0952(15) Uani 1 1 d . . . . .
Sn1 Sn 0.08582(2) 0.52793(2) 0.33515(2) 0.04100(10) Uani 1 1 d . . . . .
Sn2 Sn 0.27418(2) 0.03107(2) 0.29596(2) 0.03970(9) Uani 1 1 d . . . . .
N1 N 0.4451(3) 0.9007(4) 0.4612(3) 0.0620(15) Uani 1 1 d . . . . .
N2 N -0.0899(3) 0.4040(3) 0.1856(3) 0.0507(12) 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 O2 1.211(7) . ?
C1 O1 1.312(7) . ?
C1 C2 1.497(8) . ?
C2 C3 1.396(8) . ?
C2 C7 1.399(8) . ?
C3 C4 1.378(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(9) . ?
C5 C8 1.468(8) . ?
C6 C7 1.374(9) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.266(8) . ?
C8 H8 0.9300 . ?
C9 C14 1.366(10) . ?
C9 C10 1.380(10) . ?
C9 N1 1.427(8) . ?
C10 C11 1.372(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.326(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.340(10) . ?
C12 F1 1.343(7) . ?
C13 C14 1.413(10) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C16 C21 1.376(9) . ?
C16 C17 1.385(8) . ?
C16 Sn1 2.124(5) . ?
C17 C18 1.390(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(11) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(11) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(9) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.375(9) . ?
C22 C23 1.396(8) . ?
C22 Sn1 2.137(6) . ?
C23 C24 1.373(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.353(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.394(10) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.390(9) . ?
C28 C33 1.391(8) . ?
C28 Sn1 2.108(7) . ?
C29 C30 1.401(10) . ?
C29 H29 0.9300 . ?
C30 C31 1.360(11) . ?
C30 H30 0.9300 . ?
C31 C32 1.377(10) . ?
C31 H31 0.9300 . ?
C32 C33 1.374(9) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 O4 1.214(6) . ?
C34 O3 1.320(6) . ?
C34 C35 1.492(7) . ?
C35 C36 1.380(7) . ?
C35 C40 1.383(8) . ?
C36 C37 1.386(7) . ?
C36 H36 0.9300 . ?
C37 C38 1.382(8) . ?
C37 H37 0.9300 . ?
C38 C39 1.387(8) . ?
C38 C42 1.471(7) . ?
C39 C40 1.381(8) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C42 N2 1.253(7) . ?
C42 H42 0.9300 . ?
C43 C44 1.383(8) . ?
C43 C48 1.390(9) . ?
C43 N2 1.430(7) . ?
C44 C45 1.387(8) . ?
C44 H44 0.9300 . ?
C45 C46 1.361(10) . ?
C45 H45 0.9300 . ?
C46 C47 1.358(10) . ?
C46 F2 1.363(7) . ?
C47 C48 1.368(9) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
C49 C50 1.349(9) . ?
C49 C54 1.365(9) . ?
C49 Sn2 2.134(6) . ?
C50 C51 1.382(11) . ?
C50 H50 0.9300 . ?
C51 C52 1.366(12) . ?
C51 H51 0.9300 . ?
C52 C53 1.331(12) . ?
C52 H52 0.9300 . ?
C53 C54 1.380(10) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
C55 C60 1.378(9) . ?
C55 C56 1.391(8) . ?
C55 Sn2 2.129(7) . ?
C56 C57 1.368(9) . ?
C56 H56 0.9300 . ?
C57 C58 1.349(11) . ?
C57 H57 0.9300 . ?
C58 C59 1.381(10) . ?
C58 H58 0.9300 . ?
C59 C60 1.353(10) . ?
C59 H59 0.9300 . ?
C60 H60 0.9300 . ?
C61 C62 1.379(9) . ?
C61 C66 1.386(9) . ?
C61 Sn2 2.121(6) . ?
C62 C63 1.377(9) . ?
C62 H62 0.9300 . ?
C63 C64 1.367(11) . ?
C63 H63 0.9300 . ?
C64 C65 1.362(11) . ?
C64 H64 0.9300 . ?
C65 C66 1.384(9) . ?
C65 H65 0.9300 . ?
C66 H66 0.9300 . ?
O1 Sn1 2.062(4) . ?
O3 Sn2 2.047(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
O2 C1 O1 122.0(5) . . ?
O2 C1 C2 123.5(5) . . ?
O1 C1 C2 114.5(5) . . ?
C3 C2 C7 119.1(6) . . ?
C3 C2 C1 119.3(5) . . ?
C7 C2 C1 121.6(6) . . ?
C4 C3 C2 120.1(6) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.7(6) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.1(6) . . ?
C6 C5 C8 119.0(6) . . ?
C4 C5 C8 121.7(6) . . ?
C7 C6 C5 120.7(6) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 120.3(6) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N1 C8 C5 123.4(6) . . ?
N1 C8 H8 118.3 . . ?
C5 C8 H8 118.3 . . ?
C14 C9 C10 117.1(7) . . ?
C14 C9 N1 124.5(7) . . ?
C10 C9 N1 118.4(7) . . ?
C11 C10 C9 121.6(8) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 120.0(8) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 121.5(7) . . ?
C11 C12 F1 119.2(8) . . ?
C13 C12 F1 119.3(7) . . ?
C12 C13 C14 119.1(7) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C9 C14 C13 120.5(8) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C21 C16 C17 118.9(6) . . ?
C21 C16 Sn1 118.4(5) . . ?
C17 C16 Sn1 122.7(5) . . ?
C16 C17 C18 120.0(7) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.4(7) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.1(7) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 119.1(8) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C16 C21 C20 121.5(7) . . ?
C16 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C27 C22 C23 117.4(6) . . ?
C27 C22 Sn1 120.4(5) . . ?
C23 C22 Sn1 122.1(4) . . ?
C24 C23 C22 121.1(6) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C24 C23 120.5(7) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.3(7) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C27 119.4(7) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C22 C27 C26 121.2(7) . . ?
C22 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C29 C28 C33 117.6(6) . . ?
C29 C28 Sn1 122.7(5) . . ?
C33 C28 Sn1 119.6(5) . . ?
C28 C29 C30 120.4(7) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C31 C30 C29 120.5(8) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 119.7(8) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C33 C32 C31 120.2(7) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C28 121.5(7) . . ?
C32 C33 H33 119.2 . . ?
C28 C33 H33 119.2 . . ?
O4 C34 O3 120.7(5) . . ?
O4 C34 C35 123.5(5) . . ?
O3 C34 C35 115.9(5) . . ?
C36 C35 C40 119.8(5) . . ?
C36 C35 C34 120.5(5) . . ?
C40 C35 C34 119.6(5) . . ?
C35 C36 C37 120.1(5) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C38 C37 C36 120.7(5) . . ?
C38 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C37 C38 C39 118.6(5) . . ?
C37 C38 C42 121.8(5) . . ?
C39 C38 C42 119.6(5) . . ?
C40 C39 C38 121.1(5) . . ?
C40 C39 H39 119.4 . . ?
C38 C39 H39 119.4 . . ?
C39 C40 C35 119.7(5) . . ?
C39 C40 H40 120.2 . . ?
C35 C40 H40 120.2 . . ?
N2 C42 C38 122.7(5) . . ?
N2 C42 H42 118.6 . . ?
C38 C42 H42 118.6 . . ?
C44 C43 C48 119.0(6) . . ?
C44 C43 N2 116.7(6) . . ?
C48 C43 N2 124.3(5) . . ?
C43 C44 C45 120.7(6) . . ?
C43 C44 H44 119.7 . . ?
C45 C44 H44 119.7 . . ?
C46 C45 C44 118.0(6) . . ?
C46 C45 H45 121.0 . . ?
C44 C45 H45 121.0 . . ?
C47 C46 C45 122.5(6) . . ?
C47 C46 F2 119.3(7) . . ?
C45 C46 F2 118.1(6) . . ?
C46 C47 C48 119.6(7) . . ?
C46 C47 H47 120.2 . . ?
C48 C47 H47 120.2 . . ?
C47 C48 C43 120.0(6) . . ?
C47 C48 H48 120.0 . . ?
C43 C48 H48 120.0 . . ?
C50 C49 C54 117.3(7) . . ?
C50 C49 Sn2 122.0(5) . . ?
C54 C49 Sn2 120.6(5) . . ?
C49 C50 C51 122.2(8) . . ?
C49 C50 H50 118.9 . . ?
C51 C50 H50 118.9 . . ?
C52 C51 C50 119.1(9) . . ?
C52 C51 H51 120.4 . . ?
C50 C51 H51 120.4 . . ?
C53 C52 C51 119.4(8) . . ?
C53 C52 H52 120.3 . . ?
C51 C52 H52 120.3 . . ?
C52 C53 C54 121.0(8) . . ?
C52 C53 H53 119.5 . . ?
C54 C53 H53 119.5 . . ?
C49 C54 C53 120.9(8) . . ?
C49 C54 H54 119.6 . . ?
C53 C54 H54 119.6 . . ?
C60 C55 C56 118.6(6) . . ?
C60 C55 Sn2 122.5(5) . . ?
C56 C55 Sn2 118.9(5) . . ?
C57 C56 C55 120.4(7) . . ?
C57 C56 H56 119.8 . . ?
C55 C56 H56 119.8 . . ?
C58 C57 C56 120.0(8) . . ?
C58 C57 H57 120.0 . . ?
C56 C57 H57 120.0 . . ?
C57 C58 C59 120.3(7) . . ?
C57 C58 H58 119.8 . . ?
C59 C58 H58 119.8 . . ?
C60 C59 C58 120.2(7) . . ?
C60 C59 H59 119.9 . . ?
C58 C59 H59 119.9 . . ?
C59 C60 C55 120.4(7) . . ?
C59 C60 H60 119.8 . . ?
C55 C60 H60 119.8 . . ?
C62 C61 C66 118.5(6) . . ?
C62 C61 Sn2 118.1(5) . . ?
C66 C61 Sn2 123.3(5) . . ?
C63 C62 C61 120.7(7) . . ?
C63 C62 H62 119.6 . . ?
C61 C62 H62 119.6 . . ?
C64 C63 C62 119.5(8) . . ?
C64 C63 H63 120.3 . . ?
C62 C63 H63 120.3 . . ?
C65 C64 C63 121.4(7) . . ?
C65 C64 H64 119.3 . . ?
C63 C64 H64 119.3 . . ?
C64 C65 C66 119.0(8) . . ?
C64 C65 H65 120.5 . . ?
C66 C65 H65 120.5 . . ?
C65 C66 C61 120.8(7) . . ?
C65 C66 H66 119.6 . . ?
C61 C66 H66 119.6 . . ?
C1 O1 Sn1 110.6(4) . . ?
C34 O3 Sn2 112.6(3) . . ?
O1 Sn1 C28 110.6(2) . . ?
O1 Sn1 C16 107.5(2) . . ?
C28 Sn1 C16 120.1(2) . . ?
O1 Sn1 C22 94.1(2) . . ?
C28 Sn1 C22 110.3(2) . . ?
C16 Sn1 C22 111.1(2) . . ?
O3 Sn2 C61 109.7(2) . . ?
O3 Sn2 C55 109.36(18) . . ?
C61 Sn2 C55 118.8(2) . . ?
O3 Sn2 C49 95.0(2) . . ?
C61 Sn2 C49 110.6(2) . . ?
C55 Sn2 C49 110.8(2) . . ?
C8 N1 C9 120.0(6) . . ?
C42 N2 C43 118.4(5) . . ?

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
O2 C1 C2 C3 16.4(9) . . . . ?
O1 C1 C2 C3 -164.3(6) . . . . ?
O2 C1 C2 C7 -164.6(6) . . . . ?
O1 C1 C2 C7 14.7(8) . . . . ?
C7 C2 C3 C4 -1.5(9) . . . . ?
C1 C2 C3 C4 177.5(5) . . . . ?
C2 C3 C4 C5 -0.5(9) . . . . ?
C3 C4 C5 C6 1.6(9) . . . . ?
C3 C4 C5 C8 -173.6(6) . . . . ?
C4 C5 C6 C7 -0.6(10) . . . . ?
C8 C5 C6 C7 174.8(6) . . . . ?
C5 C6 C7 C2 -1.5(10) . . . . ?
C3 C2 C7 C6 2.5(10) . . . . ?
C1 C2 C7 C6 -176.5(6) . . . . ?
C6 C5 C8 N1 -173.9(7) . . . . ?
C4 C5 C8 N1 1.3(10) . . . . ?
C14 C9 C10 C11 -2.9(11) . . . . ?
N1 C9 C10 C11 176.2(7) . . . . ?
C9 C10 C11 C12 2.3(12) . . . . ?
C10 C11 C12 C13 0.3(13) . . . . ?
C10 C11 C12 F1 -179.0(7) . . . . ?
C11 C12 C13 C14 -2.0(14) . . . . ?
F1 C12 C13 C14 177.3(8) . . . . ?
C10 C9 C14 C13 1.2(12) . . . . ?
N1 C9 C14 C13 -177.9(7) . . . . ?
C12 C13 C14 C9 1.2(14) . . . . ?
C21 C16 C17 C18 -0.7(9) . . . . ?
Sn1 C16 C17 C18 176.5(5) . . . . ?
C16 C17 C18 C19 -0.2(10) . . . . ?
C17 C18 C19 C20 0.9(12) . . . . ?
C18 C19 C20 C21 -0.7(12) . . . . ?
C17 C16 C21 C20 0.9(10) . . . . ?
Sn1 C16 C21 C20 -176.4(6) . . . . ?
C19 C20 C21 C16 -0.3(12) . . . . ?
C27 C22 C23 C24 4.6(10) . . . . ?
Sn1 C22 C23 C24 -178.4(5) . . . . ?
C22 C23 C24 C25 -3.2(12) . . . . ?
C23 C24 C25 C26 1.3(13) . . . . ?
C24 C25 C26 C27 -0.9(13) . . . . ?
C23 C22 C27 C26 -4.2(11) . . . . ?
Sn1 C22 C27 C26 178.7(6) . . . . ?
C25 C26 C27 C22 2.4(13) . . . . ?
C33 C28 C29 C30 1.2(9) . . . . ?
Sn1 C28 C29 C30 178.0(5) . . . . ?
C28 C29 C30 C31 -0.8(11) . . . . ?
C29 C30 C31 C32 0.0(12) . . . . ?
C30 C31 C32 C33 0.4(11) . . . . ?
C31 C32 C33 C28 0.1(11) . . . . ?
C29 C28 C33 C32 -0.8(9) . . . . ?
Sn1 C28 C33 C32 -177.8(5) . . . . ?
O4 C34 C35 C36 12.7(8) . . . . ?
O3 C34 C35 C36 -167.4(5) . . . . ?
O4 C34 C35 C40 -168.5(5) . . . . ?
O3 C34 C35 C40 11.4(7) . . . . ?
C40 C35 C36 C37 0.5(8) . . . . ?
C34 C35 C36 C37 179.3(5) . . . . ?
C35 C36 C37 C38 -0.1(9) . . . . ?
C36 C37 C38 C39 0.3(8) . . . . ?
C36 C37 C38 C42 -178.1(5) . . . . ?
C37 C38 C39 C40 -1.0(9) . . . . ?
C42 C38 C39 C40 177.4(5) . . . . ?
C38 C39 C40 C35 1.4(9) . . . . ?
C36 C35 C40 C39 -1.2(8) . . . . ?
C34 C35 C40 C39 180.0(5) . . . . ?
C37 C38 C42 N2 10.2(9) . . . . ?
C39 C38 C42 N2 -168.1(6) . . . . ?
C48 C43 C44 C45 -4.0(10) . . . . ?
N2 C43 C44 C45 177.1(6) . . . . ?
C43 C44 C45 C46 3.1(10) . . . . ?
C44 C45 C46 C47 0.4(12) . . . . ?
C44 C45 C46 F2 178.8(6) . . . . ?
C45 C46 C47 C48 -2.9(12) . . . . ?
F2 C46 C47 C48 178.7(7) . . . . ?
C46 C47 C48 C43 2.0(11) . . . . ?
C44 C43 C48 C47 1.4(10) . . . . ?
N2 C43 C48 C47 -179.7(6) . . . . ?
C54 C49 C50 C51 1.0(13) . . . . ?
Sn2 C49 C50 C51 179.7(8) . . . . ?
C49 C50 C51 C52 -2.9(16) . . . . ?
C50 C51 C52 C53 3.4(16) . . . . ?
C51 C52 C53 C54 -2.2(16) . . . . ?
C50 C49 C54 C53 0.3(12) . . . . ?
Sn2 C49 C54 C53 -178.4(7) . . . . ?
C52 C53 C54 C49 0.3(15) . . . . ?
C60 C55 C56 C57 -0.4(10) . . . . ?
Sn2 C55 C56 C57 179.0(5) . . . . ?
C55 C56 C57 C58 1.3(11) . . . . ?
C56 C57 C58 C59 -1.7(12) . . . . ?
C57 C58 C59 C60 1.1(12) . . . . ?
C58 C59 C60 C55 -0.1(12) . . . . ?
C56 C55 C60 C59 -0.2(10) . . . . ?
Sn2 C55 C60 C59 -179.5(6) . . . . ?
C66 C61 C62 C63 -1.3(10) . . . . ?
Sn2 C61 C62 C63 176.5(5) . . . . ?
C61 C62 C63 C64 2.0(11) . . . . ?
C62 C63 C64 C65 -1.9(13) . . . . ?
C63 C64 C65 C66 1.1(13) . . . . ?
C64 C65 C66 C61 -0.4(12) . . . . ?
C62 C61 C66 C65 0.5(11) . . . . ?
Sn2 C61 C66 C65 -177.2(6) . . . . ?
O2 C1 O1 Sn1 -3.3(7) . . . . ?
C2 C1 O1 Sn1 177.4(4) . . . . ?
O4 C34 O3 Sn2 -3.0(7) . . . . ?
C35 C34 O3 Sn2 177.2(3) . . . . ?
C5 C8 N1 C9 176.0(6) . . . . ?
C14 C9 N1 C8 26.0(11) . . . . ?
C10 C9 N1 C8 -153.0(7) . . . . ?
C38 C42 N2 C43 -179.7(5) . . . . ?
C44 C43 N2 C42 -139.6(6) . . . . ?
C48 C43 N2 C42 41.4(9) . . . . ?

_refine_diff_density_max         0.902
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_Compound11
_database_code_depnum_ccdc_archive 'CCDC 1533452'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-12-19 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         'C32 H24 F N O2 Sn'
_chemical_formula_sum            'C32 H24 F N O2 Sn'
_chemical_formula_weight         592.21

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'
F F 0.0171 0.0103 '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'
Sn Sn -0.6537 1.4246 '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                   26.2984(8)
_cell_length_b                   9.5246(4)
_cell_length_c                   21.8019(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.563(3)
_cell_angle_gamma                90
_cell_volume                     5455.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8676
_cell_measurement_theta_max      28.2650
_cell_measurement_theta_min      3.5210

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             2384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.972
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33258
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.102
_diffrn_reflns_theta_max         28.724
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             12601
_reflns_number_gt                9989
_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_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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)+(0.0274P)²+4.9685P] 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         12601
_refine_ls_number_parameters     667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.002

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 0.65684(14) 0.1180(4) 0.37845(18) 0.0491(9) Uani 1 1 d . . . . .
C2 C 0.67757(15) 0.0217(4) 0.42747(17) 0.0478(9) Uani 1 1 d . . . . .
C3 C 0.72345(16) -0.0455(5) 0.4189(2) 0.0608(11) Uani 1 1 d . . . . .
H3 H 0.7395 -0.0355 0.3820 0.073 Uiso 1 1 calc R U . . .
C4 C 0.74545(19) -0.1276(6) 0.4652(2) 0.0748(14) Uani 1 1 d . . . . .
H4 H 0.7762 -0.1730 0.4596 0.090 Uiso 1 1 calc R U . . .
C5 C 0.7214(2) -0.1414(6) 0.5197(3) 0.0854(16) Uani 1 1 d . . . . .
H5 H 0.7364 -0.1953 0.5512 0.103 Uiso 1 1 calc R U . . .
C6 C 0.6761(2) -0.0776(5) 0.5281(2) 0.0737(14) Uani 1 1 d . . . . .
H6 H 0.6604 -0.0894 0.5651 0.088 Uiso 1 1 calc R U . . .
C7 C 0.65283(16) 0.0048(4) 0.48249(18) 0.0534(10) Uani 1 1 d . . . . .
C8 C 0.60263(17) 0.0660(5) 0.49168(19) 0.0576(11) Uani 1 1 d . . . . .
H8 H 0.5845 0.1028 0.4578 0.069 Uiso 1 1 calc R U . . .
C9 C 0.53466(19) 0.1377(6) 0.5485(2) 0.0664(13) Uani 1 1 d . . . . .
C10 C 0.5060(2) 0.1011(6) 0.5974(2) 0.0862(17) Uani 1 1 d . . . . .
H10 H 0.5179 0.0327 0.6249 0.103 Uiso 1 1 calc R U . . .
C11 C 0.4598(3) 0.1650(8) 0.6059(3) 0.102(2) Uani 1 1 d . . . . .
H11 H 0.4404 0.1389 0.6386 0.122 Uiso 1 1 calc R U . . .
C12 C 0.4432(2) 0.2648(8) 0.5668(3) 0.102(2) Uani 1 1 d . . . . .
C13 C 0.4706(3) 0.3064(8) 0.5193(3) 0.115(2) Uani 1 1 d . . . . .
H13 H 0.4586 0.3774 0.4931 0.138 Uiso 1 1 calc R U . . .
C14 C 0.5169(2) 0.2418(7) 0.5102(3) 0.100(2) Uani 1 1 d . . . . .
H14 H 0.5361 0.2696 0.4775 0.120 Uiso 1 1 calc R U . . .
C21 C 0.84998(14) 0.6070(5) 0.37142(18) 0.0488(9) Uani 1 1 d . . . . .
C22 C 0.82815(14) 0.5223(4) 0.42114(16) 0.0452(9) Uani 1 1 d . . . . .
C23 C 0.78128(15) 0.4602(5) 0.40967(19) 0.0550(10) Uani 1 1 d . . . . .
H23 H 0.7659 0.4646 0.3705 0.066 Uiso 1 1 calc R U . . .
C24 C 0.75703(16) 0.3916(5) 0.4557(2) 0.0687(13) Uani 1 1 d . . . . .
H24 H 0.7255 0.3498 0.4477 0.082 Uiso 1 1 calc R U . . .
C25 C 0.78006(17) 0.3855(6) 0.5140(2) 0.0719(14) Uani 1 1 d . . . . .
H25 H 0.7635 0.3420 0.5456 0.086 Uiso 1 1 calc R U . . .
C26 C 0.82740(16) 0.4437(5) 0.52531(18) 0.0622(12) Uani 1 1 d . . . . .
H26 H 0.8431 0.4361 0.5643 0.075 Uiso 1 1 calc R U . . .
C27 C 0.85217(14) 0.5136(4) 0.47944(17) 0.0462(9) Uani 1 1 d . . . . .
C28 C 0.90378(14) 0.5700(4) 0.49172(17) 0.0502(10) Uani 1 1 d . . . . .
H28 H 0.9229 0.5954 0.4586 0.060 Uiso 1 1 calc R U . . .
C29 C 0.97222(16) 0.6469(5) 0.55202(19) 0.0591(11) Uani 1 1 d . . . . .
C30 C 1.00174(18) 0.6138(6) 0.6037(2) 0.0735(14) Uani 1 1 d . . . . .
H30 H 0.9897 0.5505 0.6321 0.088 Uiso 1 1 calc R U . . .
C31 C 1.0494(2) 0.6744(7) 0.6136(3) 0.0890(18) Uani 1 1 d . . . . .
H31 H 1.0698 0.6509 0.6480 0.107 Uiso 1 1 calc R U . . .
C32 C 1.0657(2) 0.7670(7) 0.5727(3) 0.0893(18) Uani 1 1 d . . . . .
C33 C 1.0377(2) 0.8052(7) 0.5218(3) 0.103(2) Uani 1 1 d . . . . .
H33 H 1.0498 0.8710 0.4946 0.124 Uiso 1 1 calc R U . . .
C34 C 0.9905(2) 0.7435(7) 0.5115(3) 0.0916(18) Uani 1 1 d . . . . .
H34 H 0.9708 0.7676 0.4766 0.110 Uiso 1 1 calc R U . . .
C41 C 0.66461(13) 0.4233(4) 0.26878(18) 0.0459(9) Uani 1 1 d . . . . .
C42 C 0.65926(14) 0.5142(4) 0.3175(2) 0.0529(10) Uani 1 1 d . . . . .
H42 H 0.6399 0.4869 0.3501 0.064 Uiso 1 1 calc R U . . .
C43 C 0.68240(16) 0.6458(5) 0.3188(2) 0.0675(12) Uani 1 1 d . . . . .
H43 H 0.6774 0.7065 0.3514 0.081 Uiso 1 1 calc R U . . .
C44 C 0.71233(17) 0.6858(5) 0.2723(3) 0.0758(15) Uani 1 1 d . . . . .
H44 H 0.7285 0.7727 0.2737 0.091 Uiso 1 1 calc R U . . .
C45 C 0.71850(17) 0.5977(6) 0.2236(3) 0.0760(15) Uani 1 1 d . . . . .
H45 H 0.7385 0.6255 0.1917 0.091 Uiso 1 1 calc R U . . .
C46 C 0.69512(16) 0.4667(5) 0.2217(2) 0.0613(11) Uani 1 1 d . . . . .
H46 H 0.6999 0.4074 0.1885 0.074 Uiso 1 1 calc R U . . .
C47 C 0.64130(13) 0.1170(4) 0.18218(17) 0.0452(9) Uani 1 1 d . . . . .
C48 C 0.65209(16) -0.0251(5) 0.18317(19) 0.0560(10) Uani 1 1 d . . . . .
H48 H 0.6542 -0.0722 0.2205 0.067 Uiso 1 1 calc R U . . .
C49 C 0.65986(18) -0.0984(5) 0.1297(2) 0.0678(12) Uani 1 1 d . . . . .
H49 H 0.6676 -0.1936 0.1314 0.081 Uiso 1 1 calc R U . . .
C50 C 0.65623(18) -0.0309(6) 0.0742(2) 0.0677(13) Uani 1 1 d . . . . .
H50 H 0.6607 -0.0805 0.0381 0.081 Uiso 1 1 calc R U . . .
C51 C 0.6460(2) 0.1095(6) 0.0722(2) 0.0810(16) Uani 1 1 d . . . . .
H51 H 0.6442 0.1562 0.0347 0.097 Uiso 1 1 calc R U . . .
C52 C 0.63836(19) 0.1825(5) 0.12566(19) 0.0701(14) Uani 1 1 d . . . . .
H52 H 0.6310 0.2779 0.1236 0.084 Uiso 1 1 calc R U . . .
C53 C 0.54844(14) 0.2178(4) 0.28007(18) 0.0474(9) Uani 1 1 d . . . . .
C54 C 0.52604(17) 0.2879(5) 0.3283(2) 0.0676(13) Uani 1 1 d . . . . .
H54 H 0.5462 0.3398 0.3562 0.081 Uiso 1 1 calc R U . . .
C55 C 0.47397(19) 0.2802(6) 0.3346(3) 0.0805(16) Uani 1 1 d . . . . .
H55 H 0.4592 0.3281 0.3664 0.097 Uiso 1 1 calc R U . . .
C56 C 0.44422(18) 0.2025(6) 0.2945(3) 0.0833(17) Uani 1 1 d . . . . .
H56 H 0.4092 0.1982 0.2986 0.100 Uiso 1 1 calc R U . . .
C57 C 0.46604(18) 0.1318(7) 0.2485(3) 0.0908(18) Uani 1 1 d . . . . .
H57 H 0.4459 0.0777 0.2215 0.109 Uiso 1 1 calc R U . . .
C58 C 0.51762(16) 0.1394(6) 0.2416(2) 0.0741(14) Uani 1 1 d . . . . .
H58 H 0.5319 0.0898 0.2099 0.089 Uiso 1 1 calc R U . . .
C59 C 0.95754(14) 0.7020(4) 0.28016(18) 0.0484(9) Uani 1 1 d . . . . .
C60 C 0.98131(17) 0.7752(5) 0.3282(2) 0.0694(13) Uani 1 1 d . . . . .
H60 H 0.9620 0.8285 0.3543 0.083 Uiso 1 1 calc R U . . .
C61 C 1.03398(19) 0.7697(6) 0.3377(3) 0.0856(17) Uani 1 1 d . . . . .
H61 H 1.0496 0.8209 0.3696 0.103 Uiso 1 1 calc R U . . .
C62 C 1.06261(18) 0.6901(6) 0.3009(3) 0.0854(17) Uani 1 1 d . . . . .
H62 H 1.0977 0.6854 0.3082 0.102 Uiso 1 1 calc R U . . .
C63 C 1.04016(18) 0.6170(7) 0.2532(3) 0.0900(17) Uani 1 1 d . . . . .
H63 H 1.0599 0.5633 0.2277 0.108 Uiso 1 1 calc R U . . .
C64 C 0.98774(16) 0.6231(6) 0.2429(2) 0.0708(13) Uani 1 1 d . . . . .
H64 H 0.9726 0.5731 0.2103 0.085 Uiso 1 1 calc R U . . .
C65 C 0.86141(14) 0.5921(4) 0.17705(17) 0.0472(9) Uani 1 1 d . . . . .
C66 C 0.87505(18) 0.6480(6) 0.1210(2) 0.0707(13) Uani 1 1 d . . . . .
H66 H 0.8914 0.7346 0.1201 0.085 Uiso 1 1 calc R U . . .
C67 C 0.86452(19) 0.5761(6) 0.0669(2) 0.0744(14) Uani 1 1 d . . . . .
H67 H 0.8736 0.6149 0.0298 0.089 Uiso 1 1 calc R U . . .
C68 C 0.84090(18) 0.4485(5) 0.0675(2) 0.0667(12) Uani 1 1 d . . . . .
H68 H 0.8337 0.4006 0.0310 0.080 Uiso 1 1 calc R U . . .
C69 C 0.82796(18) 0.3919(5) 0.1221(2) 0.0687(13) Uani 1 1 d . . . . .
H69 H 0.8119 0.3049 0.1228 0.082 Uiso 1 1 calc R U . . .
C70 C 0.83855(16) 0.4627(5) 0.17650(19) 0.0558(10) Uani 1 1 d . . . . .
H70 H 0.8300 0.4219 0.2134 0.067 Uiso 1 1 calc R U . . .
C71 C 0.83691(12) 0.8961(4) 0.25765(17) 0.0428(9) Uani 1 1 d . . . . .
C72 C 0.83773(15) 0.9895(5) 0.3058(2) 0.0577(11) Uani 1 1 d . . . . .
H72 H 0.8570 0.9687 0.3414 0.069 Uiso 1 1 calc R U . . .
C73 C 0.81051(17) 1.1138(5) 0.3022(3) 0.0724(13) Uani 1 1 d . . . . .
H73 H 0.8112 1.1755 0.3353 0.087 Uiso 1 1 calc R U . . .
C75 C 0.78245(17) 1.1452(6) 0.2495(3) 0.0769(15) Uani 1 1 d . . . . .
H75 H 0.7640 1.2285 0.2469 0.092 Uiso 1 1 calc R U . . .
C76 C 0.78131(16) 1.0550(6) 0.2007(2) 0.0705(14) Uani 1 1 d . . . . .
H76 H 0.7622 1.0771 0.1650 0.085 Uiso 1 1 calc R U . . .
C77 C 0.80852(15) 0.9311(5) 0.2043(2) 0.0588(11) Uani 1 1 d . . . . .
H77 H 0.8079 0.8704 0.1709 0.071 Uiso 1 1 calc R U . . .
F1 F 0.39749(15) 0.3290(5) 0.5749(2) 0.1461(16) Uani 1 1 d . . . . .
F2 F 1.11305(12) 0.8268(5) 0.58175(18) 0.1301(14) Uani 1 1 d . . . . .
N1 N 0.58255(15) 0.0714(4) 0.54354(16) 0.0675(10) Uani 1 1 d . . . . .
N2 N 0.92301(13) 0.5852(4) 0.54487(15) 0.0597(9) Uani 1 1 d . . . . .
O1 O 0.66296(10) 0.0775(3) 0.32219(12) 0.0567(7) Uani 1 1 d . . . . .
O2 O 0.63685(11) 0.2307(3) 0.38975(13) 0.0577(7) Uani 1 1 d . . . . .
O3 O 0.84335(9) 0.5596(3) 0.31613(11) 0.0527(7) Uani 1 1 d . . . . .
O4 O 0.87193(12) 0.7193(3) 0.38161(13) 0.0640(8) Uani 1 1 d . . . . .
Sn1 Sn 0.62751(2) 0.22583(3) 0.26472(2) 0.04470(8) Uani 1 1 d . . . . .
Sn2 Sn 0.87810(2) 0.70453(3) 0.25971(2) 0.04479(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 O2 1.225(5) . ?
C1 O1 1.303(5) . ?
C1 C2 1.492(5) . ?
C2 C3 1.386(6) . ?
C2 C7 1.399(5) . ?
C3 C4 1.383(6) . ?
C4 C5 1.378(7) . ?
C5 C6 1.357(7) . ?
C6 C7 1.388(6) . ?
C7 C8 1.465(6) . ?
C8 N1 1.270(5) . ?
C9 C14 1.366(7) . ?
C9 C10 1.377(6) . ?
C9 N1 1.418(6) . ?
C10 C11 1.378(8) . ?
C11 C12 1.336(9) . ?
C12 C13 1.346(8) . ?
C12 F1 1.367(7) . ?
C13 C14 1.387(8) . ?
C21 O4 1.231(5) . ?
C21 O3 1.292(5) . ?
C21 C22 1.487(5) . ?
C22 C23 1.380(5) . ?
C22 C27 1.396(5) . ?
C23 C24 1.378(6) . ?
C24 C25 1.384(6) . ?
C25 C26 1.375(6) . ?
C26 C27 1.388(5) . ?
C27 C28 1.473(5) . ?
C28 N2 1.252(5) . ?
C29 C34 1.377(7) . ?
C29 C30 1.376(6) . ?
C29 N2 1.424(5) . ?
C30 C31 1.389(7) . ?
C31 C32 1.338(8) . ?
C32 C33 1.353(8) . ?
C32 F2 1.376(6) . ?
C33 C34 1.381(7) . ?
C41 C42 1.383(5) . ?
C41 C46 1.394(5) . ?
C41 Sn1 2.119(4) . ?
C42 C43 1.393(6) . ?
C43 C44 1.365(7) . ?
C44 C45 1.368(7) . ?
C45 C46 1.390(7) . ?
C47 C52 1.380(5) . ?
C47 C48 1.382(6) . ?
C47 Sn1 2.122(4) . ?
C48 C49 1.382(6) . ?
C49 C50 1.369(6) . ?
C50 C51 1.365(7) . ?
C51 C52 1.379(6) . ?
C53 C58 1.363(6) . ?
C53 C54 1.398(6) . ?
C53 Sn1 2.122(4) . ?
C54 C55 1.384(6) . ?
C55 C56 1.365(7) . ?
C56 C57 1.356(7) . ?
C57 C58 1.373(6) . ?
C59 C64 1.383(6) . ?
C59 C60 1.384(6) . ?
C59 Sn2 2.117(4) . ?
C60 C61 1.392(6) . ?
C61 C62 1.357(8) . ?
C62 C63 1.363(8) . ?
C63 C64 1.388(6) . ?
C65 C70 1.371(6) . ?
C65 C66 1.394(5) . ?
C65 Sn2 2.125(4) . ?
C66 C67 1.381(6) . ?
C67 C68 1.365(6) . ?
C68 C69 1.365(6) . ?
C69 C70 1.382(6) . ?
C71 C72 1.375(5) . ?
C71 C77 1.394(5) . ?
C71 Sn2 2.121(4) . ?
C72 C73 1.384(6) . ?
C73 C75 1.371(7) . ?
C75 C76 1.366(7) . ?
C76 C77 1.381(6) . ?
O1 Sn1 2.081(3) . ?
O3 Sn2 2.087(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
O2 C1 O1 121.4(4) . . ?
O2 C1 C2 122.7(4) . . ?
O1 C1 C2 115.8(4) . . ?
C3 C2 C7 120.2(4) . . ?
C3 C2 C1 118.7(4) . . ?
C7 C2 C1 121.0(4) . . ?
C4 C3 C2 120.1(4) . . ?
C5 C4 C3 119.4(5) . . ?
C6 C5 C4 120.9(5) . . ?
C5 C6 C7 121.2(5) . . ?
C6 C7 C2 118.2(4) . . ?
C6 C7 C8 119.9(4) . . ?
C2 C7 C8 121.9(4) . . ?
N1 C8 C7 123.4(4) . . ?
C14 C9 C10 118.3(5) . . ?
C14 C9 N1 123.9(4) . . ?
C10 C9 N1 117.7(5) . . ?
C9 C10 C11 120.5(6) . . ?
C12 C11 C10 119.6(6) . . ?
C11 C12 C13 121.9(7) . . ?
C11 C12 F1 120.0(7) . . ?
C13 C12 F1 118.1(8) . . ?
C12 C13 C14 118.9(7) . . ?
C9 C14 C13 120.8(6) . . ?
O4 C21 O3 121.0(4) . . ?
O4 C21 C22 122.2(4) . . ?
O3 C21 C22 116.8(4) . . ?
C23 C22 C27 120.2(4) . . ?
C23 C22 C21 118.1(3) . . ?
C27 C22 C21 121.5(4) . . ?
C24 C23 C22 120.6(4) . . ?
C23 C24 C25 119.4(4) . . ?
C26 C25 C24 120.2(4) . . ?
C25 C26 C27 121.0(4) . . ?
C26 C27 C22 118.5(4) . . ?
C26 C27 C28 120.2(4) . . ?
C22 C27 C28 121.3(3) . . ?
N2 C28 C27 122.8(4) . . ?
C34 C29 C30 118.6(5) . . ?
C34 C29 N2 123.2(4) . . ?
C30 C29 N2 118.1(5) . . ?
C29 C30 C31 120.3(5) . . ?
C32 C31 C30 118.9(5) . . ?
C31 C32 C33 123.0(6) . . ?
C31 C32 F2 119.4(6) . . ?
C33 C32 F2 117.6(7) . . ?
C32 C33 C34 118.1(6) . . ?
C29 C34 C33 121.1(5) . . ?
C42 C41 C46 117.5(4) . . ?
C42 C41 Sn1 121.7(3) . . ?
C46 C41 Sn1 120.8(3) . . ?
C41 C42 C43 121.3(4) . . ?
C44 C43 C42 120.2(5) . . ?
C43 C44 C45 119.8(5) . . ?
C44 C45 C46 120.4(5) . . ?
C45 C46 C41 120.8(5) . . ?
C52 C47 C48 117.4(4) . . ?
C52 C47 Sn1 122.1(3) . . ?
C48 C47 Sn1 120.5(3) . . ?
C49 C48 C47 121.3(4) . . ?
C50 C49 C48 120.1(4) . . ?
C51 C50 C49 119.6(4) . . ?
C50 C51 C52 120.2(5) . . ?
C51 C52 C47 121.5(4) . . ?
C58 C53 C54 117.8(4) . . ?
C58 C53 Sn1 118.8(3) . . ?
C54 C53 Sn1 123.4(3) . . ?
C55 C54 C53 120.1(5) . . ?
C56 C55 C54 120.4(5) . . ?
C57 C56 C55 119.6(5) . . ?
C56 C57 C58 120.5(5) . . ?
C53 C58 C57 121.6(5) . . ?
C64 C59 C60 117.8(4) . . ?
C64 C59 Sn2 118.0(3) . . ?
C60 C59 Sn2 124.2(3) . . ?
C59 C60 C61 120.4(5) . . ?
C62 C61 C60 120.5(5) . . ?
C61 C62 C63 120.2(5) . . ?
C62 C63 C64 119.7(5) . . ?
C59 C64 C63 121.3(5) . . ?
C70 C65 C66 117.8(4) . . ?
C70 C65 Sn2 122.3(3) . . ?
C66 C65 Sn2 119.9(3) . . ?
C67 C66 C65 120.6(4) . . ?
C68 C67 C66 120.5(4) . . ?
C69 C68 C67 119.4(4) . . ?
C68 C69 C70 120.5(4) . . ?
C65 C70 C69 121.2(4) . . ?
C72 C71 C77 118.1(4) . . ?
C72 C71 Sn2 123.4(3) . . ?
C77 C71 Sn2 118.5(3) . . ?
C71 C72 C73 121.4(4) . . ?
C75 C73 C72 119.4(5) . . ?
C76 C75 C73 120.5(5) . . ?
C75 C76 C77 120.0(5) . . ?
C76 C77 C71 120.6(5) . . ?
C8 N1 C9 119.5(4) . . ?
C28 N2 C29 118.5(4) . . ?
C1 O1 Sn1 107.2(2) . . ?
C21 O3 Sn2 105.9(2) . . ?
O1 Sn1 C41 112.60(12) . . ?
O1 Sn1 C47 95.16(13) . . ?
C41 Sn1 C47 111.92(15) . . ?
O1 Sn1 C53 107.24(13) . . ?
C41 Sn1 C53 118.55(14) . . ?
C47 Sn1 C53 108.79(14) . . ?
O3 Sn2 C59 108.81(12) . . ?
O3 Sn2 C71 110.16(12) . . ?
C59 Sn2 C71 120.83(15) . . ?
O3 Sn2 C65 95.01(13) . . ?
C59 Sn2 C65 109.71(15) . . ?
C71 Sn2 C65 109.24(15) . . ?

_refine_diff_density_max         0.473
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.065

