# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1843194'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2018-05-14 deposited with the CCDC.	2019-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13 Cl4 N3 O Sn'
_chemical_formula_weight         439.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn 0.0259 5.4591 '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                   7.006(5)
_cell_length_b                   9.684(5)
_cell_length_c                   11.987(5)
_cell_angle_alpha                69.910(5)
_cell_angle_beta                 89.440(5)
_cell_angle_gamma                84.970(5)
_cell_volume                     760.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1388
_cell_measurement_theta_min      9.2830
_cell_measurement_theta_max      58.8860

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    19.772
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.070
_exptl_absorpt_correction_T_max  0.773
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            6229
_diffrn_reflns_av_unetI/netI     0.1403
_diffrn_reflns_av_R_equivalents  0.1217
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.927
_diffrn_reflns_theta_max         66.939
_diffrn_reflns_theta_full        66.939
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2666
_reflns_number_gt                1911
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    superflip
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0895P)²+0.4421P] 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         2666
_refine_ls_number_parameters     170
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.2040
_refine_ls_wR_factor_gt          0.1708
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.014
_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
Sn1 Sn 0.25055(12) 0.63439(9) 0.42779(7) 0.0340(3) Uani 1 1 d . . . . .
Cl1 Cl 0.2451(4) 0.9936(3) 0.3799(2) 0.0296(6) Uani 1 1 d . . . . .
Cl2 Cl 0.4752(4) 0.7111(4) 0.2526(3) 0.0398(7) Uani 1 1 d D . . . .
Cl3 Cl -0.0266(4) 0.7042(4) 0.2792(3) 0.0393(7) Uani 1 1 d . . . . .
Cl4 Cl 0.2871(8) 0.3704(3) 0.4258(3) 0.0661(12) Uani 1 1 d . . . . .
O1 O 0.1666(4) 0.9768(3) 0.0909(7) 0.054(3) Uani 1 1 d D . . . .
N2 N 0.2196(13) 0.2462(11) 0.0926(9) 0.031(2) Uani 1 1 d . . . . .
H2 H 0.200736 0.155269 0.106524 0.037 Uiso 1 1 calc R U . . .
N3 N 0.2518(13) 0.3063(11) 0.1734(9) 0.030(2) Uani 1 1 d . . . . .
H3 H 0.260163 0.258383 0.248616 0.036 Uiso 1 1 calc R U . . .
N1 N 0.2969(14) 1.0483(10) -0.3703(8) 0.0282(19) Uani 1 1 d . . . . .
H1A H 0.223813 1.120345 -0.356449 0.042 Uiso 1 1 calc R U . . .
H1B H 0.261315 1.041670 -0.439194 0.042 Uiso 1 1 calc R U . . .
H1C H 0.419000 1.067912 -0.373340 0.042 Uiso 1 1 calc R U . . .
C4 C 0.2552(14) 0.6340(12) -0.0957(10) 0.024(2) Uani 1 1 d . . . . .
C1 C 0.2748(15) 0.9074(12) -0.2740(10) 0.027(2) Uani 1 1 d . . . . .
C7 C 0.2215(15) 0.3509(12) -0.0147(9) 0.024(2) Uani 1 1 d . . . . .
H7 H 0.206123 0.337426 -0.087179 0.029 Uiso 1 1 calc R U . . .
C2 C 0.2363(16) 0.7849(13) -0.3023(11) 0.032(2) Uani 1 1 d . . . . .
H2A H 0.218557 0.794519 -0.381534 0.038 Uiso 1 1 calc R U . . .
C8 C 0.2508(15) 0.4851(12) 0.0012(10) 0.025(2) Uani 1 1 d . . . . .
C6 C 0.3062(17) 0.8969(14) -0.1575(11) 0.033(3) Uani 1 1 d . . . . .
H6 H 0.332857 0.978997 -0.138881 0.040 Uiso 1 1 calc R U . . .
C9 C 0.2696(16) 0.4501(13) 0.1242(11) 0.032(3) Uani 1 1 d . . . . .
H9 H 0.290528 0.515005 0.163815 0.038 Uiso 1 1 calc R U . . .
C5 C 0.2966(18) 0.7567(13) -0.0667(11) 0.033(3) Uani 1 1 d . . . . .
H5 H 0.317968 0.746546 0.012297 0.040 Uiso 1 1 calc R U . . .
C3 C 0.2240(18) 0.6484(13) -0.2145(11) 0.034(3) Uani 1 1 d . . . . .
H3A H 0.195356 0.567612 -0.234343 0.040 Uiso 1 1 calc R U . . .
HW2 H 0.0795(5) 0.9118(4) 0.0969(13) 0.051 Uiso 1 1 d D U . . .
HW1 H 0.2727(5) 0.9170(6) 0.1226(11) 0.051 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
Sn1 Cl3 2.532(3) . ?
Sn1 Cl2 2.551(3) . ?
Sn1 Cl4 2.556(4) . ?
O1 HW2 0.9000(4) . ?
O1 HW1 0.9000(4) . ?
N2 N3 1.321(15) . ?
N2 C7 1.337(14) . ?
N2 H2 0.8600 . ?
N3 C9 1.330(16) . ?
N3 H3 0.8600 . ?
N1 C1 1.473(14) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C4 C5 1.401(17) . ?
C4 C3 1.401(17) . ?
C4 C8 1.511(15) . ?
C1 C6 1.383(18) . ?
C1 C2 1.390(17) . ?
C7 C8 1.410(16) . ?
C7 H7 0.9300 . ?
C2 C3 1.387(17) . ?
C2 H2A 0.9300 . ?
C8 C9 1.399(17) . ?
C6 C5 1.426(17) . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C3 H3A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl3 Sn1 Cl2 88.03(11) . . ?
Cl3 Sn1 Cl4 91.58(13) . . ?
Cl2 Sn1 Cl4 89.56(13) . . ?
HW2 O1 HW1 102.12(5) . . ?
N3 N2 C7 108.3(9) . . ?
N3 N2 H2 125.8 . . ?
C7 N2 H2 125.8 . . ?
N2 N3 C9 111.6(10) . . ?
N2 N3 H3 124.2 . . ?
C9 N3 H3 124.2 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C5 C4 C3 120.0(10) . . ?
C5 C4 C8 119.8(10) . . ?
C3 C4 C8 120.1(10) . . ?
C6 C1 C2 121.2(11) . . ?
C6 C1 N1 119.3(10) . . ?
C2 C1 N1 119.3(10) . . ?
N2 C7 C8 108.1(10) . . ?
N2 C7 H7 126.0 . . ?
C8 C7 H7 126.0 . . ?
C3 C2 C1 121.1(11) . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 H2A 119.4 . . ?
C9 C8 C7 105.2(10) . . ?
C9 C8 C4 128.5(11) . . ?
C7 C8 C4 126.3(10) . . ?
C1 C6 C5 118.1(11) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
N3 C9 C8 106.8(11) . . ?
N3 C9 H9 126.6 . . ?
C8 C9 H9 126.6 . . ?
C4 C5 C6 120.4(11) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C2 C3 C4 119.1(11) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?

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
_geom_hbond_publ_flag
N1 H1B Cl1 0.89 2.37 3.244(10) 165.5 1_554 yes
N1 H1C Cl1 0.89 2.38 3.205(10) 153.5 2_675 yes
N1 H1A Cl4 0.89 2.95 3.231(9) 100.4 1_564 yes
O1 HW2 Cl3 0.9000(4) 2.566(11) 3.220(6) 130.1(11) . yes
O1 HW1 Cl2 0.9000(4) 2.415(6) 3.276(5) 160.2(7) . yes
N2 H2 O1 0.86 1.84 2.674(11) 163.9 1_545 yes
N3 H3 Cl4 0.86 2.71 3.305(11) 127.5 . yes
N3 H3 Cl1 0.86 2.52 3.189(10) 135.7 1_545 yes

_refine_diff_density_max         1.840
_refine_diff_density_min         -1.217
_refine_diff_density_rms         0.248

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1843196'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2019-02-04 deposited with the CCDC.	2019-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Cl6 N4 O2 Sn'
_chemical_formula_weight         653.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn 0.0259 5.4591 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_Hall           '-C 2bc 2'

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

_cell_length_a                   7.0873(2)
_cell_length_b                   18.2022(6)
_cell_length_c                   20.2832(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2616.62(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    2313
_cell_measurement_theta_min      4.8350
_cell_measurement_theta_max      66.1930

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    13.601
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.033
_exptl_absorpt_correction_T_max  0.298
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            7457
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_av_R_equivalents  0.0844
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.359
_diffrn_reflns_theta_max         67.167
_diffrn_reflns_theta_full        67.167
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1280
_reflns_number_gt                1011
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    Superflip
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0651P)²+5.6142P] 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         1280
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1300
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.000000 0.000000 0.500000 0.0537(3) Uani 1 4 d S T P . .
Cl1 Cl 0.000000 -0.05824(12) 0.60788(10) 0.0665(5) Uani 1 2 d S T P . .
Cl2 Cl -0.2437(2) 0.08447(8) 0.53596(8) 0.0642(4) Uani 1 1 d . . . . .
O1 O 0.000000 -0.0465(4) 0.2522(4) 0.102(3) Uani 1 2 d S T P . .
N1 N 0.000000 -0.4460(3) 0.3931(3) 0.0600(16) Uani 1 2 d S T P . .
H1A H 0.000000 -0.437864 0.436339 0.090 Uiso 1 2 calc R U P . .
H1B H -0.102533 -0.471404 0.382073 0.090 Uiso 0.5 1 calc R U P . .
H1C H 0.102533 -0.471404 0.382074 0.090 Uiso 0.5 1 calc R U P . .
N2 N 0.000000 -0.0756(5) 0.1895(4) 0.087(3) Uani 1 2 d S T P . .
C4 C 0.000000 -0.2404(4) 0.2958(4) 0.0505(17) Uani 1 2 d S T P . .
C1 C 0.000000 -0.3758(4) 0.3581(4) 0.0514(17) Uani 1 2 d S T P . .
C8 C 0.000000 -0.1675(5) 0.2647(4) 0.0586(19) Uani 1 2 d S T P . .
C2 C 0.000000 -0.3715(4) 0.2917(4) 0.071(3) Uani 1 2 d S T P . .
H2 H 0.000000 -0.414454 0.266878 0.085 Uiso 1 2 calc R U P . .
C9 C 0.000000 -0.1462(6) 0.1980(5) 0.078(3) Uani 1 2 d S T P . .
H9 H 0.000000 -0.179625 0.163254 0.093 Uiso 1 2 calc R U P . .
C7 C 0.000000 -0.1017(5) 0.2954(5) 0.086(3) Uani 1 2 d S T P . .
H7 H 0.000000 -0.095608 0.340936 0.103 Uiso 1 2 calc R U P . .
C3 C 0.000000 -0.3047(5) 0.2603(4) 0.067(2) Uani 1 2 d S T P . .
H3 H 0.000000 -0.302897 0.214481 0.081 Uiso 1 2 calc R U P . .
C5 C 0.000000 -0.2454(5) 0.3632(5) 0.084(3) Uani 1 2 d S T P . .
H5 H 0.000000 -0.202605 0.388181 0.101 Uiso 1 2 calc R U P . .
C6 C 0.000000 -0.3125(5) 0.3949(4) 0.085(3) Uani 1 2 d S T P . .
H6 H 0.000000 -0.314800 0.440719 0.102 Uiso 1 2 calc R U P . .


_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
Sn1 Cl2 2.4248(14) . ?
Sn1 Cl2 2.4248(14) 11 ?
Sn1 Cl2 2.4248(14) 3_556 ?
Sn1 Cl2 2.4248(14) 9_556 ?
Sn1 Cl1 2.431(2) . ?
Sn1 Cl1 2.432(2) 9_556 ?
O1 C7 1.333(11) . ?
O1 N2 1.378(12) . ?
N1 C1 1.461(10) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C9 1.297(14) . ?
C4 C5 1.370(12) . ?
C4 C3 1.374(12) . ?
C4 C8 1.469(11) . ?
C1 C2 1.349(12) . ?
C1 C6 1.372(11) . ?
C8 C7 1.351(14) . ?
C8 C9 1.408(12) . ?
C2 C3 1.374(12) . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C5 C6 1.380(13) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Sn1 Cl2 90.85(7) . 11 ?
Cl2 Sn1 Cl2 89.15(7) . 3_556 ?
Cl2 Sn1 Cl2 180.00(5) 11 3_556 ?
Cl2 Sn1 Cl2 180.00(5) . 9_556 ?
Cl2 Sn1 Cl2 89.15(7) 11 9_556 ?
Cl2 Sn1 Cl2 90.85(7) 3_556 9_556 ?
Cl2 Sn1 Cl1 90.33(5) . . ?
Cl2 Sn1 Cl1 90.33(5) 11 . ?
Cl2 Sn1 Cl1 89.67(5) 3_556 . ?
Cl2 Sn1 Cl1 89.67(5) 9_556 . ?
Cl2 Sn1 Cl1 89.67(5) . 9_556 ?
Cl2 Sn1 Cl1 89.67(5) 11 9_556 ?
Cl2 Sn1 Cl1 90.33(5) 3_556 9_556 ?
Cl2 Sn1 Cl1 90.33(5) 9_556 9_556 ?
Cl1 Sn1 Cl1 180.0 . 9_556 ?
C7 O1 N2 108.4(7) . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C9 N2 O1 105.1(8) . . ?
C5 C4 C3 117.8(7) . . ?
C5 C4 C8 119.3(7) . . ?
C3 C4 C8 123.0(7) . . ?
C2 C1 C6 119.7(7) . . ?
C2 C1 N1 122.3(7) . . ?
C6 C1 N1 118.0(7) . . ?
C7 C8 C9 101.5(8) . . ?
C7 C8 C4 127.1(8) . . ?
C9 C8 C4 131.4(9) . . ?
C1 C2 C3 120.9(7) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
N2 C9 C8 113.6(10) . . ?
N2 C9 H9 123.2 . . ?
C8 C9 H9 123.2 . . ?
O1 C7 C8 111.5(9) . . ?
O1 C7 H7 124.3 . . ?
C8 C7 H7 124.3 . . ?
C2 C3 C4 120.7(7) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C4 C5 C6 121.6(8) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 119.3(8) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?

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
_geom_hbond_publ_flag
N1 H1B N2 0.89 2.50 2.894(10) 107.7 8_445 yes
C2 H2 O1 0.93 2.43 3.307(10) 156.3 8_445 yes
N1 H1C Cl1 0.89 2.88 3.54453(19) 133.2 7_546 yes
N1 H1C Cl2 0.89 2.86 3.424(6) 122.7 7_546 yes
N1 H1A Cl2 0.89 2.75 3.465(6) 138.6 5_545 yes
N1 H1B Cl2 0.89 2.86 3.424(6) 122.7 13_446 yes
N1 H1B Cl1 0.89 2.88 3.54453(19) 133.2 13_446 yes
N1 H1A Cl2 0.89 2.75 3.465(6) 138.6 15_445 yes

_refine_diff_density_max         1.105
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.114

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1843197'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2018-05-14 deposited with the CCDC.	2019-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 N2 O4'
_chemical_formula_weight         260.25

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                   8.4720(11)
_cell_length_b                   20.459(3)
_cell_length_c                   7.1990(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.958(16)
_cell_angle_gamma                90
_cell_volume                     1238.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1005
_cell_measurement_theta_min      2.9980
_cell_measurement_theta_max      22.4790

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98699
_exptl_absorpt_correction_T_max  1.00000
_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      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported S'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10667
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.019
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2515
_reflns_number_gt                1450
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    superflip
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0514P)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-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2515
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1407
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.85463(16) 0.52355(7) 0.1779(2) 0.0482(5) Uani 1 1 d . . . . .
O3 O 0.81211(18) 0.41579(8) 0.1847(3) 0.0654(6) Uani 1 1 d . . . . .
O2 O 1.14536(17) 0.50731(8) 0.3507(3) 0.0613(6) Uani 1 1 d . . . . .
O1 O 1.98049(17) 0.29142(8) 0.7560(3) 0.0582(5) Uani 1 1 d . . . . .
N1 N 1.11599(18) 0.39617(9) 0.3412(3) 0.0373(5) Uani 1 1 d . . . . .
H1 H 1.046368 0.366250 0.310593 0.045 Uiso 1 1 calc R U . . .
N2 N 1.9224(2) 0.22743(10) 0.7300(3) 0.0518(6) Uani 1 1 d . . . . .
C2 C 1.2894(2) 0.30885(11) 0.4606(3) 0.0420(6) Uani 1 1 d . . . . .
H2 H 1.202836 0.280662 0.441281 0.050 Uiso 1 1 calc R U . . .
C3 C 1.4363(2) 0.28495(11) 0.5321(3) 0.0442(6) Uani 1 1 d . . . . .
H3 H 1.447167 0.240764 0.561294 0.053 Uiso 1 1 calc R U . . .
C1 C 1.2696(2) 0.37460(10) 0.4173(3) 0.0337(5) Uani 1 1 d . . . . .
C4 C 1.5685(2) 0.32541(10) 0.5616(3) 0.0341(5) Uani 1 1 d . . . . .
C11 C 0.8953(2) 0.46222(11) 0.2166(3) 0.0408(6) Uani 1 1 d . . . . .
C12 C 0.6920(3) 0.53255(12) 0.0880(4) 0.0538(7) Uani 1 1 d . . . . .
H12A H 0.616909 0.514596 0.165937 0.065 Uiso 1 1 calc R U . . .
H12B H 0.677573 0.510404 -0.031978 0.065 Uiso 1 1 calc R U . . .
C8 C 1.7260(2) 0.29989(10) 0.6385(3) 0.0365(6) Uani 1 1 d . . . . .
C10 C 1.0678(2) 0.45798(11) 0.3120(3) 0.0390(6) Uani 1 1 d . . . . .
C6 C 1.4005(2) 0.41551(11) 0.4448(3) 0.0409(6) Uani 1 1 d . . . . .
H6 H 1.389462 0.459667 0.415420 0.049 Uiso 1 1 calc R U . . .
C5 C 1.5476(2) 0.39096(11) 0.5156(3) 0.0409(6) Uani 1 1 d . . . . .
H5 H 1.634526 0.419019 0.532895 0.049 Uiso 1 1 calc R U . . .
C7 C 1.7737(3) 0.23404(12) 0.6619(4) 0.0462(6) Uani 1 1 d . . . . .
H7 H 1.705825 0.198898 0.631671 0.055 Uiso 1 1 calc R U . . .
C9 C 1.8608(2) 0.33244(12) 0.7006(4) 0.0495(7) Uani 1 1 d . . . . .
H9 H 1.869443 0.377745 0.704327 0.059 Uiso 1 1 calc R U . . .
C13 C 0.6652(3) 0.60462(13) 0.0616(4) 0.0612(8) Uani 1 1 d . . . . .
H13A H 0.674452 0.625716 0.181575 0.092 Uiso 1 1 calc R U . . .
H13B H 0.560746 0.612052 -0.002772 0.092 Uiso 1 1 calc R U . . .
H13C H 0.743207 0.622203 -0.010787 0.092 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C11 1.322(3) . ?
O4 C12 1.461(3) . ?
O3 C11 1.189(3) . ?
O2 C10 1.218(3) . ?
O1 C9 1.339(3) . ?
O1 N2 1.403(2) . ?
N1 C10 1.338(3) . ?
N1 C1 1.420(2) . ?
N2 C7 1.302(3) . ?
C2 C3 1.378(3) . ?
C2 C1 1.386(3) . ?
C3 C4 1.388(3) . ?
C1 C6 1.384(3) . ?
C4 C5 1.387(3) . ?
C4 C8 1.477(3) . ?
C11 C10 1.540(3) . ?
C12 C13 1.500(3) . ?
C8 C9 1.350(3) . ?
C8 C7 1.411(3) . ?
C6 C5 1.383(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
C11 O4 C12 114.90(18) . . ?
C9 O1 N2 107.72(17) . . ?
C10 N1 C1 127.04(18) . . ?
C7 N2 O1 105.11(18) . . ?
C3 C2 C1 120.51(19) . . ?
C2 C3 C4 121.4(2) . . ?
C6 C1 C2 118.77(19) . . ?
C6 C1 N1 123.25(19) . . ?
C2 C1 N1 117.95(18) . . ?
C5 C4 C3 117.55(19) . . ?
C5 C4 C8 120.98(19) . . ?
C3 C4 C8 121.47(19) . . ?
O3 C11 O4 125.8(2) . . ?
O3 C11 C10 123.3(2) . . ?
O4 C11 C10 110.90(19) . . ?
O4 C12 C13 107.5(2) . . ?
C9 C8 C7 102.30(19) . . ?
C9 C8 C4 129.7(2) . . ?
C7 C8 C4 128.0(2) . . ?
O2 C10 N1 127.0(2) . . ?
O2 C10 C11 120.8(2) . . ?
N1 C10 C11 112.22(19) . . ?
C5 C6 C1 120.3(2) . . ?
C6 C5 C4 121.5(2) . . ?
N2 C7 C8 113.2(2) . . ?
O1 C9 C8 111.7(2) . . ?

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
_geom_hbond_publ_flag
N1 H1 N2 0.86 2.23 3.067(3) 165.0 4_465 yes
C2 H2 O1 0.93 2.63 3.506(3) 158.2 4_465 yes
C7 H7 O3 0.93 2.53 3.085(3) 118.9 4_666 yes
C9 H9 O2 0.93 2.39 3.299(3) 167.3 3_866 yes
C3 H3 C13 0.93 3.04 3.830(3) 143.7 2_745 yes

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1843198'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2018-05-14 deposited with the CCDC.	2019-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H41 N3 O3'
_chemical_formula_weight         431.61

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

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

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

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

_cell_length_a                   11.7417(14)
_cell_length_b                   9.6253(15)
_cell_length_c                   22.1211(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.154(8)
_cell_angle_gamma                90
_cell_volume                     2468.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2737
_cell_measurement_theta_min      2.8200
_cell_measurement_theta_max      29.2360

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.147
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86593
_exptl_absorpt_correction_T_max  1.00000
_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      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            11620
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.116
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5037
_reflns_number_gt                3741
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    Superflip
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0445P)²+0.9659P] 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         5037
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C5 C 0.42871(14) 0.35396(18) 0.11818(8) 0.0238(4) Uani 1 1 d . . . . .
H5 H 0.365547 0.391825 0.091001 0.029 Uiso 1 1 calc R U . . .
O3 O 0.23809(11) -0.09213(14) 0.09982(6) 0.0360(3) Uani 1 1 d . . . . .
C4 C 0.42342(13) 0.21435(18) 0.13684(7) 0.0201(4) Uani 1 1 d . . . . .
C6 C 0.52192(14) 0.43648(19) 0.13798(8) 0.0252(4) Uani 1 1 d . . . . .
H6 H 0.523404 0.530104 0.124535 0.030 Uiso 1 1 calc R U . . .
N3 N -0.11497(10) 0.99188(14) 0.11860(6) 0.0167(3) Uani 1 1 d . . . . .
C15 C -0.18891(13) 1.22970(17) 0.07779(7) 0.0201(4) Uani 1 1 d . . . . .
H15A H -0.162568 1.269856 0.118836 0.024 Uiso 1 1 calc R U . . .
H15B H -0.271282 1.204300 0.075043 0.024 Uiso 1 1 calc R U . . .
C1 C 0.61411(13) 0.38240(19) 0.17779(7) 0.0218(4) Uani 1 1 d . . . . .
C7 C 0.31743(14) -0.0165(2) 0.12222(9) 0.0289(4) Uani 1 1 d . . . . .
H7 H 0.379300 -0.059296 0.148565 0.035 Uiso 1 1 calc R U . . .
C3 C 0.51790(13) 0.16521(18) 0.17876(8) 0.0219(4) Uani 1 1 d . . . . .
H3 H 0.516472 0.072674 0.193563 0.026 Uiso 1 1 calc R U . . .
C17 C -0.24376(15) 1.46748(19) 0.03498(9) 0.0294(4) Uani 1 1 d . . . . .
H17A H -0.232396 1.533129 0.002605 0.044 Uiso 1 1 calc R U . . .
H17B H -0.325827 1.444225 0.031323 0.044 Uiso 1 1 calc R U . . .
H17C H -0.217499 1.509808 0.075065 0.044 Uiso 1 1 calc R U . . .
C11 C 0.03495(14) 0.63494(17) 0.11327(8) 0.0237(4) Uani 1 1 d . . . . .
H11A H -0.007652 0.612757 0.072103 0.028 Uiso 1 1 calc R U . . .
H11B H 0.112534 0.668743 0.108250 0.028 Uiso 1 1 calc R U . . .
N1 N 0.71218(12) 0.46891(18) 0.19845(7) 0.0306(4) Uani 1 1 d . . . . .
C2 C 0.61156(13) 0.24704(19) 0.19871(7) 0.0221(4) Uani 1 1 d . . . . .
H2 H 0.674449 0.211249 0.226731 0.027 Uiso 1 1 calc R U . . .
C8 C 0.32640(14) 0.12799(19) 0.11290(8) 0.0240(4) Uani 1 1 d . . . . .
C22 C -0.06248(13) 1.04798(17) 0.18082(7) 0.0181(3) Uani 1 1 d . . . . .
H22A H -0.114477 1.120467 0.192728 0.022 Uiso 1 1 calc R U . . .
H22B H -0.059644 0.971679 0.211032 0.022 Uiso 1 1 calc R U . . .
C23 C 0.05697(13) 1.10909(18) 0.18525(7) 0.0206(4) Uani 1 1 d . . . . .
H23A H 0.055825 1.186061 0.155478 0.025 Uiso 1 1 calc R U . . .
H23B H 0.110892 1.037120 0.174846 0.025 Uiso 1 1 calc R U . . .
C14 C -0.11883(13) 1.10176(17) 0.06914(7) 0.0174(3) Uani 1 1 d . . . . .
H14A H -0.038798 1.131012 0.066845 0.021 Uiso 1 1 calc R U . . .
H14B H -0.150679 1.059005 0.029325 0.021 Uiso 1 1 calc R U . . .
C25 C 0.21635(15) 1.2298(2) 0.25607(9) 0.0329(4) Uani 1 1 d . . . . .
H25A H 0.238898 1.262656 0.298200 0.049 Uiso 1 1 calc R U . . .
H25B H 0.272706 1.161460 0.246457 0.049 Uiso 1 1 calc R U . . .
H25C H 0.213852 1.308531 0.227799 0.049 Uiso 1 1 calc R U . . .
C19 C -0.42765(13) 0.85500(19) 0.08060(8) 0.0243(4) Uani 1 1 d . . . . .
H19A H -0.425454 0.799060 0.118321 0.029 Uiso 1 1 calc R U . . .
H19B H -0.462841 0.945927 0.087503 0.029 Uiso 1 1 calc R U . . .
C21 C -0.23539(12) 0.94397(17) 0.12494(7) 0.0185(3) Uani 1 1 d . . . . .
H21A H -0.229121 0.876053 0.158921 0.022 Uiso 1 1 calc R U . . .
H21B H -0.278938 1.024972 0.136750 0.022 Uiso 1 1 calc R U . . .
C13 C -0.04349(13) 0.87314(17) 0.09925(7) 0.0180(3) Uani 1 1 d . . . . .
H13A H -0.080050 0.840984 0.058212 0.022 Uiso 1 1 calc R U . . .
H13B H 0.033882 0.909423 0.095312 0.022 Uiso 1 1 calc R U . . .
C12 C -0.02849(13) 0.74936(17) 0.14179(8) 0.0211(4) Uani 1 1 d . . . . .
H12A H -0.104890 0.715219 0.148728 0.025 Uiso 1 1 calc R U . . .
H12B H 0.016126 0.776775 0.181812 0.025 Uiso 1 1 calc R U . . .
C24 C 0.09870(15) 1.1632(2) 0.24951(8) 0.0302(4) Uani 1 1 d . . . . .
H24A H 0.042619 1.232142 0.260208 0.036 Uiso 1 1 calc R U . . .
H24B H 0.101449 1.085132 0.278858 0.036 Uiso 1 1 calc R U . . .
C10 C 0.04738(16) 0.50407(19) 0.15190(9) 0.0316(4) Uani 1 1 d . . . . .
H10A H 0.088564 0.433334 0.131934 0.047 Uiso 1 1 calc R U . . .
H10B H 0.090883 0.525129 0.192437 0.047 Uiso 1 1 calc R U . . .
H10C H -0.029277 0.469155 0.156297 0.047 Uiso 1 1 calc R U . . .
C16 C -0.17499(14) 1.33637(18) 0.02871(8) 0.0227(4) Uani 1 1 d . . . . .
H16A H -0.092362 1.360628 0.031588 0.027 Uiso 1 1 calc R U . . .
H16B H -0.200716 1.295030 -0.012165 0.027 Uiso 1 1 calc R U . . .
C20 C -0.30475(13) 0.87820(18) 0.06868(8) 0.0210(4) Uani 1 1 d . . . . .
H20A H -0.269676 0.788435 0.059821 0.025 Uiso 1 1 calc R U . . .
H20B H -0.305233 0.939913 0.032835 0.025 Uiso 1 1 calc R U . . .
C18 C -0.50216(15) 0.7815(2) 0.02809(9) 0.0335(5) Uani 1 1 d . . . . .
H18A H -0.580037 0.769039 0.037877 0.050 Uiso 1 1 calc R U . . .
H18B H -0.506038 0.837402 -0.009214 0.050 Uiso 1 1 calc R U . . .
H18C H -0.468648 0.690522 0.021607 0.050 Uiso 1 1 calc R U . . .
N2 N 0.14995(12) 0.23611(17) 0.04650(7) 0.0293(4) Uani 1 1 d . . . . .
C9 C 0.23055(14) 0.18960(19) 0.07589(8) 0.0245(4) Uani 1 1 d . . . . .
O2 O 0.79683(11) 0.41726(17) 0.23030(6) 0.0416(4) Uani 1 1 d . . . . .
O1 O 0.70753(12) 0.59331(15) 0.18341(7) 0.0427(4) 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
C5 C6 1.367(2) . ?
C5 C4 1.410(2) . ?
C5 H5 0.9500 . ?
O3 C7 1.223(2) . ?
C4 C3 1.410(2) . ?
C4 C8 1.441(2) . ?
C6 C1 1.384(2) . ?
C6 H6 0.9500 . ?
N3 C21 1.5149(18) . ?
N3 C22 1.5151(19) . ?
N3 C14 1.517(2) . ?
N3 C13 1.519(2) . ?
C15 C14 1.510(2) . ?
C15 C16 1.522(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C1 C2 1.385(2) . ?
C1 N1 1.435(2) . ?
C7 C8 1.412(3) . ?
C7 H7 0.9500 . ?
C3 C2 1.368(2) . ?
C3 H3 0.9500 . ?
C17 C16 1.516(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C11 C10 1.516(2) . ?
C11 C12 1.522(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N1 O2 1.228(2) . ?
N1 O1 1.242(2) . ?
C2 H2 0.9500 . ?
C8 C9 1.413(2) . ?
C22 C23 1.510(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.520(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C25 C24 1.509(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C19 C18 1.514(2) . ?
C19 C20 1.524(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 C20 1.513(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C13 C12 1.511(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N2 C9 1.150(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
C6 C5 C4 122.03(16) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C3 C4 C5 116.47(15) . . ?
C3 C4 C8 122.79(16) . . ?
C5 C4 C8 120.74(15) . . ?
C5 C6 C1 119.39(16) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C21 N3 C22 105.97(11) . . ?
C21 N3 C14 110.96(11) . . ?
C22 N3 C14 111.58(12) . . ?
C21 N3 C13 111.26(12) . . ?
C22 N3 C13 111.16(12) . . ?
C14 N3 C13 106.00(11) . . ?
C14 C15 C16 109.70(13) . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C6 C1 C2 120.69(16) . . ?
C6 C1 N1 119.41(16) . . ?
C2 C1 N1 119.89(16) . . ?
O3 C7 C8 126.63(18) . . ?
O3 C7 H7 116.7 . . ?
C8 C7 H7 116.7 . . ?
C2 C3 C4 121.83(16) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C11 C12 112.15(14) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
O2 N1 O1 122.76(16) . . ?
O2 N1 C1 118.87(17) . . ?
O1 N1 C1 118.38(16) . . ?
C3 C2 C1 119.55(16) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C7 C8 C9 115.28(16) . . ?
C7 C8 C4 125.96(16) . . ?
C9 C8 C4 118.76(16) . . ?
C23 C22 N3 115.93(12) . . ?
C23 C22 H22A 108.3 . . ?
N3 C22 H22A 108.3 . . ?
C23 C22 H22B 108.3 . . ?
N3 C22 H22B 108.3 . . ?
H22A C22 H22B 107.4 . . ?
C22 C23 C24 110.62(13) . . ?
C22 C23 H23A 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
C15 C14 N3 115.56(12) . . ?
C15 C14 H14A 108.4 . . ?
N3 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
N3 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C19 C20 112.53(14) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C20 C21 N3 116.06(13) . . ?
C20 C21 H21A 108.3 . . ?
N3 C21 H21A 108.3 . . ?
C20 C21 H21B 108.3 . . ?
N3 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?
C12 C13 N3 115.62(13) . . ?
C12 C13 H13A 108.4 . . ?
N3 C13 H13A 108.4 . . ?
C12 C13 H13B 108.4 . . ?
N3 C13 H13B 108.4 . . ?
H13A C13 H13B 107.4 . . ?
C13 C12 C11 109.18(13) . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C25 C24 C23 112.92(15) . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C17 C16 C15 112.14(14) . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C21 C20 C19 108.63(13) . . ?
C21 C20 H20A 110.0 . . ?
C19 C20 H20A 110.0 . . ?
C21 C20 H20B 110.0 . . ?
C19 C20 H20B 110.0 . . ?
H20A C20 H20B 108.3 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C9 C8 177.47(19) . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1843195'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2018-05-14 deposited with the CCDC.	2019-03-28 downloaded from the CCDC.
;
_vrf_PLAT412_shelx               
;
PROBLEM: Short Intra XH3 .. XHn   H54A   ..H55D    ..       1.49 Ang. 
RESPONSE: Disordered C55 Atom which creats this artifact, even using PART
commands.
;
_vrf_PLAT097_shelx               
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.50 eA-3  
RESPONSE: Residual density from possible alifatic long chain of tetrabutylammonium
which was not take in acount, since is preferred an anisotripic treatment rather 
isotropic one to split the terminal atoms in two or more positions. 
;


_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H90 N8 O7'
_chemical_formula_weight         963.33

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                   17.8761(15)
_cell_length_b                   20.1749(11)
_cell_length_c                   31.536(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.661(8)
_cell_angle_gamma                90
_cell_volume                     11003.0(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9105
_cell_measurement_theta_min      2.1960
_cell_measurement_theta_max      25.8240

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_F_000             4208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93007
_exptl_absorpt_correction_T_max  1.00000
_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      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported S'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            149679
_diffrn_reflns_av_unetI/netI     0.0933
_diffrn_reflns_av_R_equivalents  0.1025
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.551
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             22505
_reflns_number_gt                13017
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       '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-2018/1 (Sheldrick, 2018)'
_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)+(0.1038P)²+2.9447P] 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     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00088(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         22505
_refine_ls_number_parameters     1262
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1360
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2331
_refine_ls_wR_factor_gt          0.1947
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C55 C 0.2854(4) 0.6133(4) 0.1038(2) 0.073(3) Uani 0.599(7) 1 d . . P A 1
H55A H 0.319081 0.647516 0.120755 0.109 Uiso 0.599(7) 1 calc R U P A 1
H55B H 0.316046 0.583962 0.089999 0.109 Uiso 0.599(7) 1 calc R U P A 1
H55C H 0.244635 0.634364 0.081131 0.109 Uiso 0.599(7) 1 calc R U P A 1
C55A C 0.1937(5) 0.6413(4) 0.1275(3) 0.054(3) Uiso 0.401(7) 1 d . . P A 2
H55D H 0.223757 0.680649 0.139534 0.081 Uiso 0.401(7) 1 calc R U P A 2
H55E H 0.167653 0.649020 0.096568 0.081 Uiso 0.401(7) 1 calc R U P A 2
H55F H 0.154998 0.632442 0.143891 0.081 Uiso 0.401(7) 1 calc R U P A 2
C1 C 0.88718(16) 0.52952(13) 0.24949(10) 0.0287(7) Uani 1 1 d . . . . .
C2 C 0.87267(16) 0.60499(13) 0.24647(10) 0.0269(7) Uani 1 1 d . . . . .
C3 C 0.77166(15) 0.68743(13) 0.24799(9) 0.0254(6) Uani 1 1 d . . . . .
C4 C 0.79602(16) 0.73928(13) 0.22584(10) 0.0288(7) Uani 1 1 d . . . . .
H4 H 0.834446 0.732131 0.210315 0.035 Uiso 1 1 calc R U . . .
C5 C 0.76389(16) 0.80129(13) 0.22659(10) 0.0290(7) Uani 1 1 d . . . . .
H5 H 0.781125 0.836457 0.211404 0.035 Uiso 1 1 calc R U . . .
C6 C 0.70761(15) 0.81439(13) 0.24854(10) 0.0264(7) Uani 1 1 d . . . . .
C7 C 0.68443(17) 0.76145(14) 0.27058(10) 0.0316(7) Uani 1 1 d . . . . .
H7 H 0.646296 0.768550 0.286313 0.038 Uiso 1 1 calc R U . . .
C8 C 0.71537(16) 0.69937(14) 0.27010(10) 0.0309(7) Uani 1 1 d . . . . .
H8 H 0.697916 0.664129 0.285131 0.037 Uiso 1 1 calc R U . . .
C9 C 0.59859(17) 0.89342(14) 0.25194(10) 0.0324(7) Uani 1 1 d . . . . .
H9 H 0.561413 0.861578 0.255377 0.039 Uiso 1 1 calc R U . . .
C10 C 0.67236(16) 0.88008(13) 0.24843(9) 0.0262(6) Uani 1 1 d . . . . .
C11 C 0.70225(16) 0.94297(13) 0.24418(10) 0.0287(7) Uani 1 1 d . . . . .
H11 H 0.752995 0.950542 0.241002 0.034 Uiso 1 1 calc R U . . .
C12 C 0.39353(16) 0.01050(13) 0.25426(9) 0.0260(6) Uani 1 1 d . . . . .
C13 C 0.37847(16) -0.06557(14) 0.25060(11) 0.0316(7) Uani 1 1 d . . . . .
C14 C 0.27561(15) -0.14678(12) 0.25195(9) 0.0227(6) Uani 1 1 d . . . . .
C15 C 0.30620(16) -0.20169(13) 0.23529(10) 0.0314(7) Uani 1 1 d . . . . .
H15 H 0.351216 -0.197084 0.224740 0.038 Uiso 1 1 calc R U . . .
C16 C 0.27065(16) -0.26303(13) 0.23419(10) 0.0311(7) Uani 1 1 d . . . . .
H16 H 0.291903 -0.299976 0.222645 0.037 Uiso 1 1 calc R U . . .
C17 C 0.20508(15) -0.27209(13) 0.24940(9) 0.0235(6) Uani 1 1 d . . . . .
C18 C 0.17664(16) -0.21683(13) 0.26681(9) 0.0258(6) Uani 1 1 d . . . . .
H18 H 0.132770 -0.221723 0.278375 0.031 Uiso 1 1 calc R U . . .
C19 C 0.21044(16) -0.15539(13) 0.26769(9) 0.0270(7) Uani 1 1 d . . . . .
H19 H 0.188962 -0.118522 0.279188 0.032 Uiso 1 1 calc R U . . .
C20 C 0.09054(16) -0.34709(13) 0.24872(10) 0.0271(7) Uani 1 1 d . . . . .
H20 H 0.055105 -0.314310 0.253127 0.033 Uiso 1 1 calc R U . . .
C21 C 0.16499(15) -0.33609(13) 0.24630(9) 0.0232(6) Uani 1 1 d . . . . .
C22 C 0.19136(16) -0.39947(12) 0.23925(9) 0.0233(6) Uani 1 1 d . . . . .
H22 H 0.241685 -0.408329 0.235807 0.028 Uiso 1 1 calc R U . . .
C23 C 0.36372(15) 0.00973(13) 0.00887(9) 0.0227(6) Uani 1 1 d . . . . .
C24 C 0.37806(16) 0.08460(13) 0.01802(9) 0.0239(6) Uani 1 1 d . . . . .
C25 C 0.47895(15) 0.16834(12) 0.01695(9) 0.0206(6) Uani 1 1 d . . . . .
C26 C 0.44498(16) 0.22431(13) 0.02938(10) 0.0262(6) Uani 1 1 d . . . . .
H26 H 0.399243 0.220228 0.039297 0.031 Uiso 1 1 calc R U . . .
C27 C 0.47741(15) 0.28618(13) 0.02739(9) 0.0254(6) Uani 1 1 d . . . . .
H27 H 0.453365 0.324089 0.036006 0.031 Uiso 1 1 calc R U . . .
C28 C 0.54415(14) 0.29416(12) 0.01314(9) 0.0214(6) Uani 1 1 d . . . . .
C29 C 0.57724(16) 0.23739(13) 0.00068(10) 0.0275(7) Uani 1 1 d . . . . .
H29 H 0.622837 0.241417 -0.009375 0.033 Uiso 1 1 calc R U . . .
C30 C 0.54575(15) 0.17550(13) 0.00251(10) 0.0287(7) Uani 1 1 d . . . . .
H30 H 0.569769 0.137599 -0.006121 0.034 Uiso 1 1 calc R U . . .
C31 C 0.65576(16) 0.36927(12) 0.00810(10) 0.0259(6) Uani 1 1 d . . . . .
H31 H 0.692503 0.335811 0.006786 0.031 Uiso 1 1 calc R U . . .
C32 C 0.58150(15) 0.35892(12) 0.01112(9) 0.0214(6) Uani 1 1 d . . . . .
C33 C 0.55195(15) 0.42346(12) 0.01220(9) 0.0231(6) Uani 1 1 d . . . . .
H33 H 0.501063 0.433005 0.014471 0.028 Uiso 1 1 calc R U . . .
C34 C 0.14096(15) 0.50905(13) 0.00169(10) 0.0252(6) Uani 1 1 d . . . . .
C35 C 0.12911(15) 0.58506(13) -0.00013(10) 0.0246(6) Uani 1 1 d . . . . .
C36 C 0.02919(15) 0.66807(12) 0.00427(9) 0.0218(6) Uani 1 1 d . . . . .
C37 C 0.06586(16) 0.72428(13) -0.00486(10) 0.0306(7) Uani 1 1 d . . . . .
H37 H 0.114011 0.721007 -0.012300 0.037 Uiso 1 1 calc R U . . .
C38 C 0.03188(16) 0.78596(13) -0.00310(10) 0.0307(7) Uani 1 1 d . . . . .
H38 H 0.057125 0.824431 -0.009969 0.037 Uiso 1 1 calc R U . . .
C39 C -0.03719(15) 0.79300(12) 0.00829(9) 0.0243(6) Uani 1 1 d . . . . .
C40 C -0.07226(16) 0.73562(13) 0.01833(10) 0.0278(7) Uani 1 1 d . . . . .
H40 H -0.119185 0.738885 0.027127 0.033 Uiso 1 1 calc R U . . .
C41 C -0.04018(15) 0.67415(13) 0.01576(9) 0.0254(6) Uani 1 1 d . . . . .
H41 H -0.065971 0.635549 0.021947 0.030 Uiso 1 1 calc R U . . .
C42 C -0.15292(16) 0.86720(13) 0.00368(10) 0.0279(7) Uani 1 1 d . . . . .
H42 H -0.191656 0.833825 -0.001164 0.034 Uiso 1 1 calc R U . . .
C43 C -0.07526(15) 0.85726(12) 0.00893(9) 0.0233(6) Uani 1 1 d . . . . .
C44 C -0.04432(16) 0.92164(12) 0.01450(9) 0.0253(6) Uani 1 1 d . . . . .
H44 H 0.009044 0.931338 0.018610 0.030 Uiso 1 1 calc R U . . .
C48 C 0.12501(18) 0.38345(14) 0.10070(10) 0.0339(7) Uani 1 1 d . . . . .
H48A H 0.134489 0.407456 0.075175 0.041 Uiso 1 1 calc R U . . .
H48B H 0.078878 0.355153 0.089864 0.041 Uiso 1 1 calc R U . . .
C49 C 0.19356(19) 0.33922(15) 0.11935(11) 0.0410(8) Uani 1 1 d . . . . .
H49A H 0.183356 0.312213 0.143486 0.049 Uiso 1 1 calc R U . . .
H49B H 0.239870 0.366777 0.131460 0.049 Uiso 1 1 calc R U . . .
C50 C 0.2086(2) 0.29390(17) 0.08392(12) 0.0504(9) Uani 1 1 d . . . . .
H50A H 0.162138 0.266419 0.072008 0.061 Uiso 1 1 calc R U . . .
H50B H 0.217877 0.321206 0.059667 0.061 Uiso 1 1 calc R U . . .
C51 C 0.2775(2) 0.24898(18) 0.10106(14) 0.0617(11) Uani 1 1 d . . . . .
H51A H 0.285110 0.220688 0.077244 0.093 Uiso 1 1 calc R U . . .
H51B H 0.323822 0.275986 0.112345 0.093 Uiso 1 1 calc R U . . .
H51C H 0.268097 0.221211 0.124684 0.093 Uiso 1 1 calc R U . . .
C52 C 0.17307(18) 0.48201(14) 0.14746(10) 0.0346(7) Uani 1 1 d . . . . .
H52A H 0.218493 0.457151 0.164561 0.042 Uiso 1 1 calc R U . . .
H52B H 0.158453 0.514413 0.167532 0.042 Uiso 1 1 calc R U . . .
C53 C 0.19723(19) 0.52011(15) 0.11151(11) 0.0423(8) Uani 1 1 d . . . . .
H53A H 0.150874 0.538505 0.090686 0.051 Uiso 1 1 calc R U . . .
H53B H 0.223295 0.489757 0.095143 0.051 Uiso 1 1 calc R U . . .
C54 C 0.2523(2) 0.57668(18) 0.13149(15) 0.0650(12) Uani 1 1 d . . . . .
H54A H 0.223654 0.607712 0.145920 0.078 Uiso 1 1 calc R U . A 1
H54B H 0.294742 0.557538 0.154749 0.078 Uiso 1 1 calc R U . A 1
C56 C 0.09484(17) 0.40085(15) 0.17337(10) 0.0340(7) Uani 1 1 d . . . . .
H56A H 0.141836 0.375139 0.187224 0.041 Uiso 1 1 calc R U . . .
H56B H 0.088938 0.435828 0.194304 0.041 Uiso 1 1 calc R U . . .
C57 C 0.02588(18) 0.35522(15) 0.16597(11) 0.0386(8) Uani 1 1 d . . . . .
H57A H 0.023909 0.327424 0.139836 0.046 Uiso 1 1 calc R U . . .
H57B H -0.022032 0.382021 0.160139 0.046 Uiso 1 1 calc R U . . .
C58 C 0.02944(19) 0.31080(15) 0.20521(11) 0.0391(8) Uani 1 1 d . . . . .
H58A H -0.014867 0.279754 0.197965 0.047 Uiso 1 1 calc R U . . .
H58B H 0.077374 0.284070 0.210678 0.047 Uiso 1 1 calc R U . . .
C59 C 0.0279(2) 0.34735(17) 0.24681(11) 0.0469(9) Uani 1 1 d . . . . .
H59A H 0.030370 0.315355 0.270511 0.070 Uiso 1 1 calc R U . . .
H59B H 0.072354 0.377363 0.254820 0.070 Uiso 1 1 calc R U . . .
H59C H -0.020041 0.373040 0.242086 0.070 Uiso 1 1 calc R U . . .
C60 C 0.03399(17) 0.46968(14) 0.10767(10) 0.0345(7) Uani 1 1 d . . . . .
H60A H 0.043197 0.488526 0.080446 0.041 Uiso 1 1 calc R U . . .
H60B H -0.008233 0.436792 0.099026 0.041 Uiso 1 1 calc R U . . .
C61 C 0.00719(19) 0.52518(16) 0.13312(12) 0.0432(9) Uani 1 1 d . . . . .
H61A H 0.001419 0.507845 0.161492 0.052 Uiso 1 1 calc R U . . .
H61B H 0.046491 0.560847 0.139267 0.052 Uiso 1 1 calc R U . . .
C62 C -0.0686(2) 0.55280(17) 0.10731(12) 0.0514(10) Uani 1 1 d . . . . .
H62A H -0.108525 0.517769 0.103703 0.062 Uiso 1 1 calc R U . . .
H62B H -0.063808 0.565188 0.077741 0.062 Uiso 1 1 calc R U . . .
C63 C -0.0953(2) 0.61251(18) 0.12821(16) 0.0688(13) Uani 1 1 d . . . . .
H63A H -0.144858 0.627972 0.109768 0.103 Uiso 1 1 calc R U . . .
H63B H -0.101520 0.600459 0.157225 0.103 Uiso 1 1 calc R U . . .
H63C H -0.056756 0.647927 0.131236 0.103 Uiso 1 1 calc R U . . .
C64 C 0.4920(3) 0.7396(2) -0.15330(16) 0.0890(17) Uani 1 1 d . . . . .
H64A H 0.508471 0.718752 -0.177517 0.134 Uiso 1 1 calc R U . . .
H64B H 0.537063 0.758159 -0.132259 0.134 Uiso 1 1 calc R U . . .
H64C H 0.467375 0.706277 -0.138651 0.134 Uiso 1 1 calc R U . . .
C65 C 0.4347(2) 0.7945(2) -0.17107(14) 0.0718(13) Uani 1 1 d . . . . .
H65A H 0.459810 0.826946 -0.186544 0.086 Uiso 1 1 calc R U . . .
H65B H 0.390265 0.775171 -0.192922 0.086 Uiso 1 1 calc R U . . .
C66 C 0.40535(19) 0.82975(17) -0.13802(12) 0.0450(9) Uani 1 1 d . . . . .
H66A H 0.447670 0.856231 -0.119300 0.054 Uiso 1 1 calc R U . . .
H66B H 0.388017 0.797120 -0.119074 0.054 Uiso 1 1 calc R U . . .
C67 C 0.33878(17) 0.87510(15) -0.15863(10) 0.0328(7) Uani 1 1 d . . . . .
H67A H 0.357690 0.908945 -0.176144 0.039 Uiso 1 1 calc R U . . .
H67B H 0.298781 0.848655 -0.179136 0.039 Uiso 1 1 calc R U . . .
C68 C 0.35521(18) 0.96159(14) -0.10033(10) 0.0334(7) Uani 1 1 d . . . . .
H68A H 0.331939 0.978303 -0.077050 0.040 Uiso 1 1 calc R U . . .
H68B H 0.404355 0.939350 -0.085745 0.040 Uiso 1 1 calc R U . . .
C69 C 0.37340(18) 1.01991(14) -0.12567(10) 0.0356(8) Uani 1 1 d . . . . .
H69A H 0.324669 1.042038 -0.141086 0.043 Uiso 1 1 calc R U . . .
H69B H 0.399469 1.004206 -0.148015 0.043 Uiso 1 1 calc R U . . .
C70 C 0.4250(2) 1.06917(15) -0.09574(11) 0.0432(9) Uani 1 1 d . . . . .
H70A H 0.397502 1.086591 -0.074508 0.052 Uiso 1 1 calc R U . . .
H70B H 0.472110 1.046113 -0.078964 0.052 Uiso 1 1 calc R U . . .
C71 C 0.4482(2) 1.12629(17) -0.12041(13) 0.0539(10) Uani 1 1 d . . . . .
H71A H 0.481482 1.156669 -0.099656 0.081 Uiso 1 1 calc R U . . .
H71B H 0.476498 1.109430 -0.141046 0.081 Uiso 1 1 calc R U . . .
H71C H 0.401879 1.149915 -0.136589 0.081 Uiso 1 1 calc R U . . .
C72 C 0.22853(16) 0.94340(15) -0.15442(10) 0.0330(7) Uani 1 1 d . . . . .
H72A H 0.193596 0.908614 -0.170535 0.040 Uiso 1 1 calc R U . . .
H72B H 0.243135 0.972249 -0.176423 0.040 Uiso 1 1 calc R U . . .
C73 C 0.18428(18) 0.98472(16) -0.12869(11) 0.0386(8) Uani 1 1 d . . . . .
H73A H 0.164965 0.955929 -0.108349 0.046 Uiso 1 1 calc R U . . .
H73B H 0.218989 1.018438 -0.111140 0.046 Uiso 1 1 calc R U . . .
C74 C 0.1169(2) 1.0186(2) -0.16018(13) 0.0614(11) Uani 1 1 d . . . . .
H74A H 0.136688 1.045798 -0.181066 0.074 Uiso 1 1 calc R U . . .
H74B H 0.082187 0.984361 -0.177220 0.074 Uiso 1 1 calc R U . . .
C75 C 0.0718(2) 1.0614(2) -0.13751(15) 0.0680(12) Uani 1 1 d . . . . .
H75A H 0.029103 1.082039 -0.159209 0.102 Uiso 1 1 calc R U . . .
H75B H 0.051062 1.034536 -0.117243 0.102 Uiso 1 1 calc R U . . .
H75C H 0.105573 1.095985 -0.121090 0.102 Uiso 1 1 calc R U . . .
C76 C 0.27999(18) 0.86182(14) -0.09508(10) 0.0340(7) Uani 1 1 d . . . . .
H76A H 0.328044 0.840749 -0.077734 0.041 Uiso 1 1 calc R U . . .
H76B H 0.257244 0.887017 -0.074465 0.041 Uiso 1 1 calc R U . . .
C77 C 0.22416(18) 0.80804(15) -0.11577(11) 0.0383(8) Uani 1 1 d . . . . .
H77A H 0.172198 0.827499 -0.127525 0.046 Uiso 1 1 calc R U . . .
H77B H 0.241028 0.788175 -0.140524 0.046 Uiso 1 1 calc R U . . .
C78 C 0.2197(2) 0.75487(16) -0.08298(11) 0.0451(9) Uani 1 1 d . . . . .
H78A H 0.206587 0.775318 -0.057264 0.054 Uiso 1 1 calc R U . . .
H78B H 0.270948 0.733379 -0.072785 0.054 Uiso 1 1 calc R U . . .
C79 C 0.1592(2) 0.70240(16) -0.10267(12) 0.0500(9) Uani 1 1 d . . . . .
H79A H 0.157852 0.668677 -0.080497 0.075 Uiso 1 1 calc R U . . .
H79B H 0.108243 0.723401 -0.112302 0.075 Uiso 1 1 calc R U . . .
H79C H 0.172563 0.681488 -0.127813 0.075 Uiso 1 1 calc R U . . .
C80 C 0.5988(3) 0.5695(2) -0.12815(15) 0.0730(13) Uani 1 1 d . . . . .
H80A H 0.636713 0.597901 -0.108488 0.110 Uiso 1 1 calc R U . . .
H80B H 0.624722 0.542960 -0.146216 0.110 Uiso 1 1 calc R U . . .
H80C H 0.558931 0.597128 -0.147134 0.110 Uiso 1 1 calc R U . . .
C81 C 0.5613(3) 0.5237(2) -0.10115(14) 0.0700(13) Uani 1 1 d . . . . .
H81A H 0.602084 0.496691 -0.081570 0.084 Uiso 1 1 calc R U . . .
H81B H 0.536329 0.550830 -0.082487 0.084 Uiso 1 1 calc R U . . .
C82 C 0.5024(2) 0.47836(16) -0.12864(11) 0.0456(9) Uani 1 1 d . . . . .
H82A H 0.526491 0.452108 -0.148180 0.055 Uiso 1 1 calc R U . . .
H82B H 0.459979 0.504924 -0.147211 0.055 Uiso 1 1 calc R U . . .
C83 C 0.46970(19) 0.43190(15) -0.10000(10) 0.0391(8) Uani 1 1 d . . . . .
H83A H 0.452950 0.458672 -0.077745 0.047 Uiso 1 1 calc R U . . .
H83B H 0.511660 0.402217 -0.084210 0.047 Uiso 1 1 calc R U . . .
C84 C 0.5217(3) 0.3023(3) -0.22208(17) 0.1021(18) Uani 1 1 d . . . . .
H84A H 0.526482 0.271722 -0.245393 0.153 Uiso 1 1 calc R U . . .
H84B H 0.480996 0.334805 -0.233910 0.153 Uiso 1 1 calc R U . . .
H84C H 0.570913 0.325354 -0.210657 0.153 Uiso 1 1 calc R U . . .
C85 C 0.5008(2) 0.26344(17) -0.18518(12) 0.0500(9) Uani 1 1 d . . . . .
H85A H 0.541567 0.230027 -0.173893 0.060 Uiso 1 1 calc R U . . .
H85B H 0.451697 0.239474 -0.197134 0.060 Uiso 1 1 calc R U . . .
C86 C 0.4922(2) 0.30722(15) -0.14742(11) 0.0437(9) Uani 1 1 d . . . . .
H86A H 0.486674 0.279088 -0.122661 0.052 Uiso 1 1 calc R U . . .
H86B H 0.539100 0.334785 -0.137213 0.052 Uiso 1 1 calc R U . . .
C87 C 0.42181(19) 0.35172(15) -0.16181(10) 0.0377(8) Uani 1 1 d . . . . .
H87A H 0.376893 0.324317 -0.176712 0.045 Uiso 1 1 calc R U . . .
H87B H 0.431377 0.384195 -0.183380 0.045 Uiso 1 1 calc R U . . .
C88 C 0.2422(3) 0.1970(2) -0.09349(14) 0.0710(13) Uani 1 1 d . . . . .
H88A H 0.235193 0.167531 -0.070064 0.106 Uiso 1 1 calc R U . . .
H88B H 0.193698 0.220497 -0.106171 0.106 Uiso 1 1 calc R U . . .
H88C H 0.256687 0.170704 -0.116298 0.106 Uiso 1 1 calc R U . . .
C89 C 0.3051(2) 0.24651(18) -0.07490(12) 0.0559(10) Uani 1 1 d . . . . .
H89A H 0.353743 0.222559 -0.061613 0.067 Uiso 1 1 calc R U . . .
H89B H 0.290719 0.272379 -0.051482 0.067 Uiso 1 1 calc R U . . .
C90 C 0.31842(19) 0.29346(16) -0.10976(11) 0.0421(8) Uani 1 1 d . . . . .
H90A H 0.332123 0.267588 -0.133392 0.051 Uiso 1 1 calc R U . . .
H90B H 0.270057 0.317950 -0.122735 0.051 Uiso 1 1 calc R U . . .
C91 C 0.38232(19) 0.34227(15) -0.09106(10) 0.0371(8) Uani 1 1 d . . . . .
H91A H 0.429539 0.317179 -0.076714 0.045 Uiso 1 1 calc R U . . .
H91B H 0.367203 0.368777 -0.068143 0.045 Uiso 1 1 calc R U . . .
C92 C 0.3160(2) 0.58874(18) -0.13108(12) 0.0594(11) Uani 1 1 d . . . . .
H92A H 0.288596 0.629283 -0.143209 0.089 Uiso 1 1 calc R U . . .
H92B H 0.346625 0.597189 -0.101106 0.089 Uiso 1 1 calc R U . . .
H92C H 0.350360 0.575001 -0.149248 0.089 Uiso 1 1 calc R U . . .
C93 C 0.2577(2) 0.53408(18) -0.13059(13) 0.0578(11) Uani 1 1 d . . . . .
H93A H 0.226221 0.526314 -0.160849 0.069 Uiso 1 1 calc R U . . .
H93B H 0.222485 0.548510 -0.112690 0.069 Uiso 1 1 calc R U . . .
C94 C 0.2972(2) 0.46897(16) -0.11187(11) 0.0463(9) Uani 1 1 d . . . . .
H94A H 0.338240 0.478675 -0.084989 0.056 Uiso 1 1 calc R U . . .
H94B H 0.258715 0.439687 -0.103639 0.056 Uiso 1 1 calc R U . . .
C95 C 0.33248(19) 0.43315(16) -0.14439(11) 0.0426(9) Uani 1 1 d . . . . .
H95A H 0.348810 0.466598 -0.163205 0.051 Uiso 1 1 calc R U . . .
H95B H 0.291988 0.405430 -0.163541 0.051 Uiso 1 1 calc R U . . .
C96 C 0.0326(2) 0.77197(18) 0.13613(14) 0.0703(13) Uani 1 1 d . . . . .
H96A H 0.023656 0.741120 0.158357 0.105 Uiso 1 1 calc R U . . .
H96B H -0.015506 0.795584 0.122739 0.105 Uiso 1 1 calc R U . . .
H96C H 0.049540 0.747200 0.113505 0.105 Uiso 1 1 calc R U . . .
C97 C 0.0949(2) 0.82174(16) 0.15760(11) 0.0464(9) Uani 1 1 d . . . . .
H97A H 0.077852 0.845852 0.180864 0.056 Uiso 1 1 calc R U . . .
H97B H 0.142880 0.797482 0.171633 0.056 Uiso 1 1 calc R U . . .
C98 C 0.11208(19) 0.87130(15) 0.12536(10) 0.0380(8) Uani 1 1 d . . . . .
H98A H 0.064632 0.896520 0.111621 0.046 Uiso 1 1 calc R U . . .
H98B H 0.129078 0.847646 0.101925 0.046 Uiso 1 1 calc R U . . .
C99 C 0.17523(17) 0.91886(14) 0.14882(10) 0.0318(7) Uani 1 1 d . . . . .
H99A H 0.155923 0.943858 0.170898 0.038 Uiso 1 1 calc R U . . .
H99B H 0.220245 0.892441 0.164788 0.038 Uiso 1 1 calc R U . . .
C100 C 0.2510(3) 0.7909(2) 0.05689(18) 0.0834(15) Uani 1 1 d . . . . .
H10O H 0.259234 0.760207 0.034437 0.125 Uiso 1 1 calc R U . . .
H10P H 0.253093 0.766504 0.084030 0.125 Uiso 1 1 calc R U . . .
H10Q H 0.200238 0.812045 0.046677 0.125 Uiso 1 1 calc R U . . .
C101 C 0.3086(3) 0.8394(2) 0.06478(14) 0.0682(12) Uani 1 1 d . . . . .
H10K H 0.306960 0.863697 0.037280 0.082 Uiso 1 1 calc R U . . .
H10L H 0.359892 0.818090 0.074687 0.082 Uiso 1 1 calc R U . . .
C102 C 0.2974(2) 0.88719(19) 0.09903(13) 0.0642(12) Uani 1 1 d . . . . .
H10M H 0.344512 0.914742 0.108631 0.077 Uiso 1 1 calc R U . . .
H10N H 0.291015 0.861895 0.124779 0.077 Uiso 1 1 calc R U . . .
C103 C 0.2280(2) 0.93241(16) 0.08324(10) 0.0411(8) Uani 1 1 d . . . . .
H10A H 0.184133 0.905742 0.066186 0.049 Uiso 1 1 calc R U . . .
H10B H 0.240627 0.965992 0.063232 0.049 Uiso 1 1 calc R U . . .
C104 C 0.4433(2) 1.03677(19) 0.14904(14) 0.0584(10) Uani 1 1 d . . . . .
H10R H 0.492905 1.054271 0.166117 0.088 Uiso 1 1 calc R U . . .
H10S H 0.432970 0.994131 0.161345 0.088 Uiso 1 1 calc R U . . .
H10T H 0.445205 1.030552 0.118521 0.088 Uiso 1 1 calc R U . . .
C105 C 0.37938(18) 1.08525(17) 0.15082(12) 0.0458(9) Uani 1 1 d . . . . .
H10E H 0.378733 1.092068 0.181810 0.055 Uiso 1 1 calc R U . . .
H10F H 0.390957 1.128457 0.139024 0.055 Uiso 1 1 calc R U . . .
C106 C 0.30019(18) 1.06260(16) 0.12535(12) 0.0435(8) Uani 1 1 d . . . . .
H10G H 0.302780 1.047853 0.095809 0.052 Uiso 1 1 calc R U . . .
H10H H 0.263699 1.100329 0.121701 0.052 Uiso 1 1 calc R U . . .
C107 C 0.27011(17) 1.00592(14) 0.14845(10) 0.0330(7) Uani 1 1 d . . . . .
H10C H 0.313030 0.974492 0.159828 0.040 Uiso 1 1 calc R U . . .
H10D H 0.254033 1.024167 0.173924 0.040 Uiso 1 1 calc R U . . .
C108 C 0.0160(3) 1.1510(2) 0.13351(15) 0.0903(17) Uani 1 1 d . . . . .
H10U H -0.023238 1.180215 0.115443 0.136 Uiso 1 1 calc R U . . .
H10V H -0.007231 1.125226 0.153244 0.136 Uiso 1 1 calc R U . . .
H10W H 0.058592 1.177808 0.150828 0.136 Uiso 1 1 calc R U . . .
C109 C 0.0464(2) 1.10453(17) 0.10428(12) 0.0494(9) Uani 1 1 d . . . . .
H10I H 0.068609 1.130949 0.083995 0.059 Uiso 1 1 calc R U . . .
H10J H 0.002813 1.078387 0.086410 0.059 Uiso 1 1 calc R U . . .
C110 C 0.10754(18) 1.05746(15) 0.12973(10) 0.0351(7) Uani 1 1 d . . . . .
H11C H 0.150477 1.083133 0.148590 0.042 Uiso 1 1 calc R U . . .
H11D H 0.084978 1.028956 0.148853 0.042 Uiso 1 1 calc R U . . .
C111 C 0.13809(17) 1.01487(14) 0.09865(10) 0.0328(7) Uani 1 1 d . . . . .
H11E H 0.156852 1.044269 0.078407 0.039 Uiso 1 1 calc R U . . .
H11F H 0.094706 0.988501 0.080803 0.039 Uiso 1 1 calc R U . . .
N1 N 0.80060(13) 0.62221(10) 0.24810(8) 0.0261(6) Uani 1 1 d . . . . .
H1 H 0.768433 0.589680 0.249353 0.031 Uiso 1 1 calc R U . . .
N2 N 0.58867(14) 0.95864(12) 0.24968(8) 0.0324(6) Uani 1 1 d . . . . .
H2 H 0.545519 0.978520 0.251030 0.039 Uiso 1 1 calc R U . . .
N3 N 0.65201(14) 0.99098(11) 0.24509(8) 0.0330(6) Uani 1 1 d . . . . .
N4 N 0.30688(12) -0.08274(10) 0.25280(8) 0.0245(5) Uani 1 1 d . . . . .
H4A H 0.275789 -0.049845 0.255051 0.029 Uiso 1 1 calc R U . . .
N5 N 0.07663(13) -0.41202(11) 0.24378(8) 0.0279(6) Uani 1 1 d . . . . .
H5A H 0.032334 -0.430599 0.244310 0.033 Uiso 1 1 calc R U . . .
N6 N 0.13812(13) -0.44573(10) 0.23791(8) 0.0260(5) Uani 1 1 d . . . . .
N7 N 0.44963(12) 0.10324(10) 0.01684(8) 0.0243(5) Uani 1 1 d . . . . .
H7A H 0.482281 0.070973 0.015880 0.029 Uiso 1 1 calc R U . . .
N8 N 0.66746(13) 0.43453(10) 0.00733(8) 0.0261(5) Uani 1 1 d . . . . .
H8A H 0.711270 0.452752 0.005521 0.031 Uiso 1 1 calc R U . . .
N9 N 0.60394(13) 0.46935(10) 0.00966(8) 0.0271(6) Uani 1 1 d . . . . .
N10 N 0.05813(12) 0.60319(10) 0.00233(8) 0.0240(5) Uani 1 1 d . . . . .
H10 H 0.025530 0.570683 0.002798 0.029 Uiso 1 1 calc R U . . .
N11 N -0.16433(13) 0.93259(10) 0.00662(8) 0.0270(6) Uani 1 1 d . . . . .
H11A H -0.209940 0.950721 0.004389 0.032 Uiso 1 1 calc R U . . .
N12 N -0.09808(13) 0.96726(11) 0.01336(8) 0.0276(6) Uani 1 1 d . . . . .
N13 N 0.10700(14) 0.43385(11) 0.13242(8) 0.0306(6) Uani 1 1 d . . . . .
N14 N 0.30107(13) 0.91036(11) -0.12708(8) 0.0285(6) Uani 1 1 d . . . . .
N15 N 0.40163(15) 0.38917(12) -0.12417(8) 0.0351(6) Uani 1 1 d . . . . .
N16 N 0.20260(14) 0.96797(11) 0.11987(8) 0.0293(6) Uani 1 1 d . . . . .
O1 O 0.83470(12) 0.49469(9) 0.25710(8) 0.0393(6) Uani 1 1 d . . . . .
O2 O 0.95054(12) 0.51060(9) 0.24433(9) 0.0466(6) Uani 1 1 d . . . . .
O3 O 0.92267(12) 0.64433(9) 0.24382(8) 0.0431(6) Uani 1 1 d . . . . .
O4 O 0.46082(11) 0.02865(9) 0.25801(7) 0.0344(5) Uani 1 1 d . . . . .
O5 O 0.33641(11) 0.04593(9) 0.25363(7) 0.0334(5) Uani 1 1 d . . . . .
O6 O 0.42762(13) -0.10418(10) 0.24616(11) 0.0661(9) Uani 1 1 d . . . . .
O7 O 0.42076(11) -0.02462(9) 0.00878(7) 0.0336(5) Uani 1 1 d . . . . .
O8 O 0.29501(11) -0.00893(9) 0.00167(7) 0.0330(5) Uani 1 1 d . . . . .
O9 O 0.32769(11) 0.12090(9) 0.02425(8) 0.0361(5) Uani 1 1 d . . . . .
O10 O 0.20559(11) 0.48985(9) -0.00182(8) 0.0371(6) Uani 1 1 d . . . . .
O11 O 0.08661(11) 0.47514(9) 0.00713(7) 0.0315(5) Uani 1 1 d . . . . .
O12 O 0.18065(12) 0.62290(9) -0.00262(8) 0.0430(6) Uani 1 1 d . . . . .
O13 O 0.67591(15) 0.60270(11) 0.00033(10) 0.0565(7) Uani 1 1 d D . . . .
H13A H 0.727(2) 0.588(2) -0.0013(14) 0.085 Uiso 1 1 d D U . . .
H13B H 0.643(2) 0.5608(18) -0.0009(14) 0.085 Uiso 1 1 d D U . . .
O14 O 0.83743(13) 0.09477(10) 0.02761(8) 0.0389(6) Uani 1 1 d D . . . .
H14A H 0.8692(18) 0.0595(16) 0.0252(12) 0.058 Uiso 1 1 d D U . . .
H14B H 0.7894(18) 0.0752(16) 0.0221(12) 0.058 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
C55 C54 1.385(7) . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C55A C54 1.658(9) . ?
C55A H55D 0.9800 . ?
C55A H55E 0.9800 . ?
C55A H55F 0.9800 . ?
C1 O2 1.244(3) . ?
C1 O1 1.243(3) . ?
C1 C2 1.543(4) . ?
C2 O3 1.214(3) . ?
C2 N1 1.348(3) . ?
C3 C8 1.383(4) . ?
C3 C4 1.388(4) . ?
C3 N1 1.414(3) . ?
C4 C5 1.379(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(4) . ?
C6 C10 1.467(4) . ?
C7 C8 1.371(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N2 1.327(4) . ?
C9 C10 1.378(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(4) . ?
C11 N3 1.326(4) . ?
C11 H11 0.9500 . ?
C12 O4 1.234(3) . ?
C12 O5 1.242(3) . ?
C12 C13 1.557(4) . ?
C13 O6 1.209(3) . ?
C13 N4 1.344(3) . ?
C14 C19 1.388(4) . ?
C14 C15 1.395(4) . ?
C14 N4 1.405(3) . ?
C15 C16 1.388(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(4) . ?
C17 C21 1.468(4) . ?
C18 C19 1.376(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 N5 1.335(3) . ?
C20 C21 1.370(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.400(4) . ?
C22 N6 1.326(3) . ?
C22 H22 0.9500 . ?
C23 O7 1.233(3) . ?
C23 O8 1.249(3) . ?
C23 C24 1.547(4) . ?
C24 O9 1.215(3) . ?
C24 N7 1.343(3) . ?
C25 C26 1.385(4) . ?
C25 C30 1.389(4) . ?
C25 N7 1.414(3) . ?
C26 C27 1.384(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.387(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.390(4) . ?
C28 C32 1.476(4) . ?
C29 C30 1.377(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 N8 1.334(3) . ?
C31 C32 1.371(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.409(4) . ?
C33 N9 1.329(3) . ?
C33 H33 0.9500 . ?
C34 O11 1.235(3) . ?
C34 O10 1.250(3) . ?
C34 C35 1.547(4) . ?
C35 O12 1.214(3) . ?
C35 N10 1.341(3) . ?
C36 C37 1.376(4) . ?
C36 C41 1.383(4) . ?
C36 N10 1.414(3) . ?
C37 C38 1.392(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.378(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.391(4) . ?
C39 C43 1.467(4) . ?
C40 C41 1.377(4) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 N11 1.342(3) . ?
C42 C43 1.371(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.405(4) . ?
C44 N12 1.325(3) . ?
C44 H44 0.9500 . ?
C48 N13 1.517(4) . ?
C48 C49 1.510(4) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 C50 1.519(4) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 C51 1.514(5) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 N13 1.510(3) . ?
C52 C53 1.520(4) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.535(4) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C56 C57 1.509(4) . ?
C56 N13 1.517(4) . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
C57 C58 1.516(4) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C58 C59 1.511(5) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C60 C61 1.524(4) . ?
C60 N13 1.523(4) . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C61 C62 1.500(4) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C62 C63 1.507(5) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 0.9800 . ?
C64 C65 1.516(5) . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?
C65 C66 1.465(5) . ?
C65 H65A 0.9900 . ?
C65 H65B 0.9900 . ?
C66 C67 1.511(4) . ?
C66 H66A 0.9900 . ?
C66 H66B 0.9900 . ?
C67 N14 1.513(4) . ?
C67 H67A 0.9900 . ?
C67 H67B 0.9900 . ?
C68 C69 1.504(4) . ?
C68 N14 1.518(3) . ?
C68 H68A 0.9900 . ?
C68 H68B 0.9900 . ?
C69 C70 1.513(4) . ?
C69 H69A 0.9900 . ?
C69 H69B 0.9900 . ?
C70 C71 1.507(5) . ?
C70 H70A 0.9900 . ?
C70 H70B 0.9900 . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C72 N14 1.518(3) . ?
C72 C73 1.518(4) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C73 C74 1.516(4) . ?
C73 H73A 0.9900 . ?
C73 H73B 0.9900 . ?
C74 C75 1.482(5) . ?
C74 H74A 0.9900 . ?
C74 H74B 0.9900 . ?
C75 H75A 0.9800 . ?
C75 H75B 0.9800 . ?
C75 H75C 0.9800 . ?
C76 C77 1.506(4) . ?
C76 N14 1.520(4) . ?
C76 H76A 0.9900 . ?
C76 H76B 0.9900 . ?
C77 C78 1.506(4) . ?
C77 H77A 0.9900 . ?
C77 H77B 0.9900 . ?
C78 C79 1.529(4) . ?
C78 H78A 0.9900 . ?
C78 H78B 0.9900 . ?
C79 H79A 0.9800 . ?
C79 H79B 0.9800 . ?
C79 H79C 0.9800 . ?
C80 C81 1.522(5) . ?
C80 H80A 0.9800 . ?
C80 H80B 0.9800 . ?
C80 H80C 0.9800 . ?
C81 C82 1.495(5) . ?
C81 H81A 0.9900 . ?
C81 H81B 0.9900 . ?
C82 C83 1.518(5) . ?
C82 H82A 0.9900 . ?
C82 H82B 0.9900 . ?
C83 N15 1.528(4) . ?
C83 H83A 0.9900 . ?
C83 H83B 0.9900 . ?
C84 C85 1.525(6) . ?
C84 H84A 0.9800 . ?
C84 H84B 0.9800 . ?
C84 H84C 0.9800 . ?
C85 C86 1.522(5) . ?
C85 H85A 0.9900 . ?
C85 H85B 0.9900 . ?
C86 C87 1.518(4) . ?
C86 H86A 0.9900 . ?
C86 H86B 0.9900 . ?
C87 N15 1.525(4) . ?
C87 H87A 0.9900 . ?
C87 H87B 0.9900 . ?
C88 C89 1.508(5) . ?
C88 H88A 0.9800 . ?
C88 H88B 0.9800 . ?
C88 H88C 0.9800 . ?
C89 C90 1.515(5) . ?
C89 H89A 0.9900 . ?
C89 H89B 0.9900 . ?
C90 C91 1.510(4) . ?
C90 H90A 0.9900 . ?
C90 H90B 0.9900 . ?
C91 N15 1.512(4) . ?
C91 H91A 0.9900 . ?
C91 H91B 0.9900 . ?
C92 C93 1.520(5) . ?
C92 H92A 0.9800 . ?
C92 H92B 0.9800 . ?
C92 H92C 0.9800 . ?
C93 C94 1.537(5) . ?
C93 H93A 0.9900 . ?
C93 H93B 0.9900 . ?
C94 C95 1.516(5) . ?
C94 H94A 0.9900 . ?
C94 H94B 0.9900 . ?
C95 N15 1.524(4) . ?
C95 H95A 0.9900 . ?
C95 H95B 0.9900 . ?
C96 C97 1.525(5) . ?
C96 H96A 0.9800 . ?
C96 H96B 0.9800 . ?
C96 H96C 0.9800 . ?
C97 C98 1.512(5) . ?
C97 H97A 0.9900 . ?
C97 H97B 0.9900 . ?
C98 C99 1.523(4) . ?
C98 H98A 0.9900 . ?
C98 H98B 0.9900 . ?
C99 N16 1.510(4) . ?
C99 H99A 0.9900 . ?
C99 H99B 0.9900 . ?
C100 C101 1.396(6) . ?
C100 H10O 0.9800 . ?
C100 H10P 0.9800 . ?
C100 H10Q 0.9800 . ?
C101 C102 1.498(5) . ?
C101 H10K 0.9900 . ?
C101 H10L 0.9900 . ?
C102 C103 1.519(4) . ?
C102 H10M 0.9900 . ?
C102 H10N 0.9900 . ?
C103 N16 1.524(4) . ?
C103 H10A 0.9900 . ?
C103 H10B 0.9900 . ?
C104 C105 1.515(5) . ?
C104 H10R 0.9800 . ?
C104 H10S 0.9800 . ?
C104 H10T 0.9800 . ?
C105 C106 1.511(4) . ?
C105 H10E 0.9900 . ?
C105 H10F 0.9900 . ?
C106 C107 1.525(4) . ?
C106 H10G 0.9900 . ?
C106 H10H 0.9900 . ?
C107 N16 1.518(4) . ?
C107 H10C 0.9900 . ?
C107 H10D 0.9900 . ?
C108 C109 1.510(5) . ?
C108 H10U 0.9800 . ?
C108 H10V 0.9800 . ?
C108 H10W 0.9800 . ?
C109 C110 1.516(4) . ?
C109 H10I 0.9900 . ?
C109 H10J 0.9900 . ?
C110 C111 1.506(4) . ?
C110 H11C 0.9900 . ?
C110 H11D 0.9900 . ?
C111 N16 1.511(3) . ?
C111 H11E 0.9900 . ?
C111 H11F 0.9900 . ?
N1 H1 0.8800 . ?
N2 N3 1.346(3) . ?
N2 H2 0.8800 . ?
N4 H4A 0.8800 . ?
N5 N6 1.345(3) . ?
N5 H5A 0.8800 . ?
N7 H7A 0.8800 . ?
N8 N9 1.353(3) . ?
N8 H8A 0.8800 . ?
N10 H10 0.8800 . ?
N11 N12 1.345(3) . ?
N11 H11A 0.8800 . ?
O13 H13A 0.97(3) . ?
O13 H13B 1.02(3) . ?
O14 H14A 0.93(3) . ?
O14 H14B 0.92(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
C54 C55 H55A 109.5 . . ?
C54 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C54 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C54 C55A H55D 109.5 . . ?
C54 C55A H55E 109.5 . . ?
H55D C55A H55E 109.5 . . ?
C54 C55A H55F 109.5 . . ?
H55D C55A H55F 109.5 . . ?
H55E C55A H55F 109.5 . . ?
O2 C1 O1 127.5(3) . . ?
O2 C1 C2 116.0(2) . . ?
O1 C1 C2 116.5(3) . . ?
O3 C2 N1 124.2(3) . . ?
O3 C2 C1 122.3(3) . . ?
N1 C2 C1 113.5(2) . . ?
C8 C3 C4 118.9(3) . . ?
C8 C3 N1 118.3(3) . . ?
C4 C3 N1 122.8(3) . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 122.7(3) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C5 C6 C7 116.7(3) . . ?
C5 C6 C10 122.5(3) . . ?
C7 C6 C10 120.8(3) . . ?
C8 C7 C6 121.5(3) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C3 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
N2 C9 C10 107.9(3) . . ?
N2 C9 H9 126.1 . . ?
C10 C9 H9 126.1 . . ?
C9 C10 C11 103.2(2) . . ?
C9 C10 C6 126.6(3) . . ?
C11 C10 C6 130.3(3) . . ?
N3 C11 C10 112.6(3) . . ?
N3 C11 H11 123.7 . . ?
C10 C11 H11 123.7 . . ?
O4 C12 O5 127.4(3) . . ?
O4 C12 C13 116.5(2) . . ?
O5 C12 C13 116.1(2) . . ?
O6 C13 N4 124.7(3) . . ?
O6 C13 C12 121.8(3) . . ?
N4 C13 C12 113.5(2) . . ?
C19 C14 C15 118.7(2) . . ?
C19 C14 N4 118.3(2) . . ?
C15 C14 N4 123.0(3) . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 122.1(3) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C16 C17 C18 117.1(2) . . ?
C16 C17 C21 122.3(3) . . ?
C18 C17 C21 120.6(3) . . ?
C19 C18 C17 121.8(3) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C14 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
N5 C20 C21 107.9(2) . . ?
N5 C20 H20 126.1 . . ?
C21 C20 H20 126.1 . . ?
C20 C21 C22 103.4(2) . . ?
C20 C21 C17 127.1(2) . . ?
C22 C21 C17 129.5(3) . . ?
N6 C22 C21 112.3(2) . . ?
N6 C22 H22 123.8 . . ?
C21 C22 H22 123.8 . . ?
O7 C23 O8 127.3(2) . . ?
O7 C23 C24 116.8(2) . . ?
O8 C23 C24 115.9(2) . . ?
O9 C24 N7 125.9(2) . . ?
O9 C24 C23 121.6(2) . . ?
N7 C24 C23 112.5(2) . . ?
C26 C25 C30 118.9(2) . . ?
C26 C25 N7 124.7(2) . . ?
C30 C25 N7 116.4(2) . . ?
C25 C26 C27 120.2(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C28 C27 C26 121.6(2) . . ?
C28 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C27 C28 C29 117.3(2) . . ?
C27 C28 C32 123.5(2) . . ?
C29 C28 C32 119.2(2) . . ?
C30 C29 C28 121.8(3) . . ?
C30 C29 H29 119.1 . . ?
C28 C29 H29 119.1 . . ?
C29 C30 C25 120.2(3) . . ?
C29 C30 H30 119.9 . . ?
C25 C30 H30 119.9 . . ?
N8 C31 C32 108.1(2) . . ?
N8 C31 H31 126.0 . . ?
C32 C31 H31 126.0 . . ?
C31 C32 C33 103.7(2) . . ?
C31 C32 C28 126.5(2) . . ?
C33 C32 C28 129.8(2) . . ?
N9 C33 C32 111.7(2) . . ?
N9 C33 H33 124.1 . . ?
C32 C33 H33 124.1 . . ?
O11 C34 O10 128.2(2) . . ?
O11 C34 C35 116.7(2) . . ?
O10 C34 C35 115.1(2) . . ?
O12 C35 N10 125.2(2) . . ?
O12 C35 C34 121.8(2) . . ?
N10 C35 C34 113.0(2) . . ?
C37 C36 C41 119.2(2) . . ?
C37 C36 N10 123.7(2) . . ?
C41 C36 N10 117.1(2) . . ?
C36 C37 C38 119.5(3) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C39 C38 C37 122.1(3) . . ?
C39 C38 H38 118.9 . . ?
C37 C38 H38 118.9 . . ?
C38 C39 C40 117.3(2) . . ?
C38 C39 C43 123.0(2) . . ?
C40 C39 C43 119.7(3) . . ?
C41 C40 C39 121.2(3) . . ?
C41 C40 H40 119.4 . . ?
C39 C40 H40 119.4 . . ?
C40 C41 C36 120.6(3) . . ?
C40 C41 H41 119.7 . . ?
C36 C41 H41 119.7 . . ?
N11 C42 C43 107.6(2) . . ?
N11 C42 H42 126.2 . . ?
C43 C42 H42 126.2 . . ?
C42 C43 C44 103.6(2) . . ?
C42 C43 C39 125.9(2) . . ?
C44 C43 C39 130.5(2) . . ?
N12 C44 C43 112.3(2) . . ?
N12 C44 H44 123.9 . . ?
C43 C44 H44 123.9 . . ?
N13 C48 C49 115.2(2) . . ?
N13 C48 H48A 108.5 . . ?
C49 C48 H48A 108.5 . . ?
N13 C48 H48B 108.5 . . ?
C49 C48 H48B 108.5 . . ?
H48A C48 H48B 107.5 . . ?
C48 C49 C50 110.3(3) . . ?
C48 C49 H49A 109.6 . . ?
C50 C49 H49A 109.6 . . ?
C48 C49 H49B 109.6 . . ?
C50 C49 H49B 109.6 . . ?
H49A C49 H49B 108.1 . . ?
C51 C50 C49 112.1(3) . . ?
C51 C50 H50A 109.2 . . ?
C49 C50 H50A 109.2 . . ?
C51 C50 H50B 109.2 . . ?
C49 C50 H50B 109.2 . . ?
H50A C50 H50B 107.9 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N13 C52 C53 116.0(2) . . ?
N13 C52 H52A 108.3 . . ?
C53 C52 H52A 108.3 . . ?
N13 C52 H52B 108.3 . . ?
C53 C52 H52B 108.3 . . ?
H52A C52 H52B 107.4 . . ?
C52 C53 C54 110.1(3) . . ?
C52 C53 H53A 109.6 . . ?
C54 C53 H53A 109.6 . . ?
C52 C53 H53B 109.6 . . ?
C54 C53 H53B 109.6 . . ?
H53A C53 H53B 108.2 . . ?
C55 C54 C53 118.0(5) . . ?
C53 C54 C55A 103.0(4) . . ?
C55 C54 H54A 107.8 . . ?
C53 C54 H54A 107.8 . . ?
C55 C54 H54B 107.8 . . ?
C53 C54 H54B 107.8 . . ?
H54A C54 H54B 107.1 . . ?
C57 C56 N13 115.1(2) . . ?
C57 C56 H56A 108.5 . . ?
N13 C56 H56A 108.5 . . ?
C57 C56 H56B 108.5 . . ?
N13 C56 H56B 108.5 . . ?
H56A C56 H56B 107.5 . . ?
C56 C57 C58 111.8(3) . . ?
C56 C57 H57A 109.3 . . ?
C58 C57 H57A 109.3 . . ?
C56 C57 H57B 109.3 . . ?
C58 C57 H57B 109.3 . . ?
H57A C57 H57B 107.9 . . ?
C59 C58 C57 114.5(3) . . ?
C59 C58 H58A 108.6 . . ?
C57 C58 H58A 108.6 . . ?
C59 C58 H58B 108.6 . . ?
C57 C58 H58B 108.6 . . ?
H58A C58 H58B 107.6 . . ?
C58 C59 H59A 109.5 . . ?
C58 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
C58 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C61 C60 N13 114.9(2) . . ?
C61 C60 H60A 108.5 . . ?
N13 C60 H60A 108.5 . . ?
C61 C60 H60B 108.5 . . ?
N13 C60 H60B 108.5 . . ?
H60A C60 H60B 107.5 . . ?
C62 C61 C60 110.4(3) . . ?
C62 C61 H61A 109.6 . . ?
C60 C61 H61A 109.6 . . ?
C62 C61 H61B 109.6 . . ?
C60 C61 H61B 109.6 . . ?
H61A C61 H61B 108.1 . . ?
C61 C62 C63 113.7(3) . . ?
C61 C62 H62A 108.8 . . ?
C63 C62 H62A 108.8 . . ?
C61 C62 H62B 108.8 . . ?
C63 C62 H62B 108.8 . . ?
H62A C62 H62B 107.7 . . ?
C62 C63 H63A 109.5 . . ?
C62 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C62 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C65 C64 H64A 109.5 . . ?
C65 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C65 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C66 C65 C64 115.0(4) . . ?
C66 C65 H65A 108.5 . . ?
C64 C65 H65A 108.5 . . ?
C66 C65 H65B 108.5 . . ?
C64 C65 H65B 108.5 . . ?
H65A C65 H65B 107.5 . . ?
C65 C66 C67 111.9(3) . . ?
C65 C66 H66A 109.2 . . ?
C67 C66 H66A 109.2 . . ?
C65 C66 H66B 109.2 . . ?
C67 C66 H66B 109.2 . . ?
H66A C66 H66B 107.9 . . ?
N14 C67 C66 115.8(3) . . ?
N14 C67 H67A 108.3 . . ?
C66 C67 H67A 108.3 . . ?
N14 C67 H67B 108.3 . . ?
C66 C67 H67B 108.3 . . ?
H67A C67 H67B 107.4 . . ?
C69 C68 N14 115.5(2) . . ?
C69 C68 H68A 108.4 . . ?
N14 C68 H68A 108.4 . . ?
C69 C68 H68B 108.4 . . ?
N14 C68 H68B 108.4 . . ?
H68A C68 H68B 107.5 . . ?
C68 C69 C70 111.2(3) . . ?
C68 C69 H69A 109.4 . . ?
C70 C69 H69A 109.4 . . ?
C68 C69 H69B 109.4 . . ?
C70 C69 H69B 109.4 . . ?
H69A C69 H69B 108.0 . . ?
C71 C70 C69 112.6(3) . . ?
C71 C70 H70A 109.1 . . ?
C69 C70 H70A 109.1 . . ?
C71 C70 H70B 109.1 . . ?
C69 C70 H70B 109.1 . . ?
H70A C70 H70B 107.8 . . ?
C70 C71 H71A 109.5 . . ?
C70 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C70 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
N14 C72 C73 115.0(2) . . ?
N14 C72 H72A 108.5 . . ?
C73 C72 H72A 108.5 . . ?
N14 C72 H72B 108.5 . . ?
C73 C72 H72B 108.5 . . ?
H72A C72 H72B 107.5 . . ?
C74 C73 C72 109.4(3) . . ?
C74 C73 H73A 109.8 . . ?
C72 C73 H73A 109.8 . . ?
C74 C73 H73B 109.8 . . ?
C72 C73 H73B 109.8 . . ?
H73A C73 H73B 108.2 . . ?
C75 C74 C73 112.7(3) . . ?
C75 C74 H74A 109.1 . . ?
C73 C74 H74A 109.1 . . ?
C75 C74 H74B 109.1 . . ?
C73 C74 H74B 109.1 . . ?
H74A C74 H74B 107.8 . . ?
C74 C75 H75A 109.5 . . ?
C74 C75 H75B 109.5 . . ?
H75A C75 H75B 109.5 . . ?
C74 C75 H75C 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?
C77 C76 N14 115.1(2) . . ?
C77 C76 H76A 108.5 . . ?
N14 C76 H76A 108.5 . . ?
C77 C76 H76B 108.5 . . ?
N14 C76 H76B 108.5 . . ?
H76A C76 H76B 107.5 . . ?
C78 C77 C76 111.1(3) . . ?
C78 C77 H77A 109.4 . . ?
C76 C77 H77A 109.4 . . ?
C78 C77 H77B 109.4 . . ?
C76 C77 H77B 109.4 . . ?
H77A C77 H77B 108.0 . . ?
C77 C78 C79 111.7(3) . . ?
C77 C78 H78A 109.3 . . ?
C79 C78 H78A 109.3 . . ?
C77 C78 H78B 109.3 . . ?
C79 C78 H78B 109.3 . . ?
H78A C78 H78B 107.9 . . ?
C78 C79 H79A 109.5 . . ?
C78 C79 H79B 109.5 . . ?
H79A C79 H79B 109.5 . . ?
C78 C79 H79C 109.5 . . ?
H79A C79 H79C 109.5 . . ?
H79B C79 H79C 109.5 . . ?
C81 C80 H80A 109.5 . . ?
C81 C80 H80B 109.5 . . ?
H80A C80 H80B 109.5 . . ?
C81 C80 H80C 109.5 . . ?
H80A C80 H80C 109.5 . . ?
H80B C80 H80C 109.5 . . ?
C82 C81 C80 113.1(3) . . ?
C82 C81 H81A 109.0 . . ?
C80 C81 H81A 109.0 . . ?
C82 C81 H81B 109.0 . . ?
C80 C81 H81B 109.0 . . ?
H81A C81 H81B 107.8 . . ?
C81 C82 C83 110.7(3) . . ?
C81 C82 H82A 109.5 . . ?
C83 C82 H82A 109.5 . . ?
C81 C82 H82B 109.5 . . ?
C83 C82 H82B 109.5 . . ?
H82A C82 H82B 108.1 . . ?
C82 C83 N15 115.4(3) . . ?
C82 C83 H83A 108.4 . . ?
N15 C83 H83A 108.4 . . ?
C82 C83 H83B 108.4 . . ?
N15 C83 H83B 108.4 . . ?
H83A C83 H83B 107.5 . . ?
C85 C84 H84A 109.5 . . ?
C85 C84 H84B 109.5 . . ?
H84A C84 H84B 109.5 . . ?
C85 C84 H84C 109.5 . . ?
H84A C84 H84C 109.5 . . ?
H84B C84 H84C 109.5 . . ?
C84 C85 C86 113.1(3) . . ?
C84 C85 H85A 109.0 . . ?
C86 C85 H85A 109.0 . . ?
C84 C85 H85B 109.0 . . ?
C86 C85 H85B 109.0 . . ?
H85A C85 H85B 107.8 . . ?
C87 C86 C85 110.5(3) . . ?
C87 C86 H86A 109.6 . . ?
C85 C86 H86A 109.6 . . ?
C87 C86 H86B 109.6 . . ?
C85 C86 H86B 109.6 . . ?
H86A C86 H86B 108.1 . . ?
C86 C87 N15 113.7(2) . . ?
C86 C87 H87A 108.8 . . ?
N15 C87 H87A 108.8 . . ?
C86 C87 H87B 108.8 . . ?
N15 C87 H87B 108.8 . . ?
H87A C87 H87B 107.7 . . ?
C89 C88 H88A 109.5 . . ?
C89 C88 H88B 109.5 . . ?
H88A C88 H88B 109.5 . . ?
C89 C88 H88C 109.5 . . ?
H88A C88 H88C 109.5 . . ?
H88B C88 H88C 109.5 . . ?
C88 C89 C90 111.8(3) . . ?
C88 C89 H89A 109.3 . . ?
C90 C89 H89A 109.3 . . ?
C88 C89 H89B 109.3 . . ?
C90 C89 H89B 109.3 . . ?
H89A C89 H89B 107.9 . . ?
C91 C90 C89 111.5(3) . . ?
C91 C90 H90A 109.3 . . ?
C89 C90 H90A 109.3 . . ?
C91 C90 H90B 109.3 . . ?
C89 C90 H90B 109.3 . . ?
H90A C90 H90B 108.0 . . ?
C90 C91 N15 114.9(3) . . ?
C90 C91 H91A 108.6 . . ?
N15 C91 H91A 108.6 . . ?
C90 C91 H91B 108.6 . . ?
N15 C91 H91B 108.6 . . ?
H91A C91 H91B 107.5 . . ?
C93 C92 H92A 109.5 . . ?
C93 C92 H92B 109.5 . . ?
H92A C92 H92B 109.5 . . ?
C93 C92 H92C 109.5 . . ?
H92A C92 H92C 109.5 . . ?
H92B C92 H92C 109.5 . . ?
C92 C93 C94 112.0(3) . . ?
C92 C93 H93A 109.2 . . ?
C94 C93 H93A 109.2 . . ?
C92 C93 H93B 109.2 . . ?
C94 C93 H93B 109.2 . . ?
H93A C93 H93B 107.9 . . ?
C95 C94 C93 112.1(3) . . ?
C95 C94 H94A 109.2 . . ?
C93 C94 H94A 109.2 . . ?
C95 C94 H94B 109.2 . . ?
C93 C94 H94B 109.2 . . ?
H94A C94 H94B 107.9 . . ?
C94 C95 N15 115.2(3) . . ?
C94 C95 H95A 108.5 . . ?
N15 C95 H95A 108.5 . . ?
C94 C95 H95B 108.5 . . ?
N15 C95 H95B 108.5 . . ?
H95A C95 H95B 107.5 . . ?
C97 C96 H96A 109.5 . . ?
C97 C96 H96B 109.5 . . ?
H96A C96 H96B 109.5 . . ?
C97 C96 H96C 109.5 . . ?
H96A C96 H96C 109.5 . . ?
H96B C96 H96C 109.5 . . ?
C98 C97 C96 112.8(3) . . ?
C98 C97 H97A 109.0 . . ?
C96 C97 H97A 109.0 . . ?
C98 C97 H97B 109.0 . . ?
C96 C97 H97B 109.0 . . ?
H97A C97 H97B 107.8 . . ?
C97 C98 C99 110.0(3) . . ?
C97 C98 H98A 109.7 . . ?
C99 C98 H98A 109.7 . . ?
C97 C98 H98B 109.7 . . ?
C99 C98 H98B 109.7 . . ?
H98A C98 H98B 108.2 . . ?
N16 C99 C98 115.7(2) . . ?
N16 C99 H99A 108.4 . . ?
C98 C99 H99A 108.4 . . ?
N16 C99 H99B 108.4 . . ?
C98 C99 H99B 108.4 . . ?
H99A C99 H99B 107.4 . . ?
C101 C100 H10O 109.5 . . ?
C101 C100 H10P 109.5 . . ?
H10O C100 H10P 109.5 . . ?
C101 C100 H10Q 109.5 . . ?
H10O C100 H10Q 109.5 . . ?
H10P C100 H10Q 109.5 . . ?
C100 C101 C102 110.7(4) . . ?
C100 C101 H10K 109.5 . . ?
C102 C101 H10K 109.5 . . ?
C100 C101 H10L 109.5 . . ?
C102 C101 H10L 109.5 . . ?
H10K C101 H10L 108.1 . . ?
C101 C102 C103 113.4(3) . . ?
C101 C102 H10M 108.9 . . ?
C103 C102 H10M 108.9 . . ?
C101 C102 H10N 108.9 . . ?
C103 C102 H10N 108.9 . . ?
H10M C102 H10N 107.7 . . ?
C102 C103 N16 114.2(3) . . ?
C102 C103 H10A 108.7 . . ?
N16 C103 H10A 108.7 . . ?
C102 C103 H10B 108.7 . . ?
N16 C103 H10B 108.7 . . ?
H10A C103 H10B 107.6 . . ?
C105 C104 H10R 109.5 . . ?
C105 C104 H10S 109.5 . . ?
H10R C104 H10S 109.5 . . ?
C105 C104 H10T 109.5 . . ?
H10R C104 H10T 109.5 . . ?
H10S C104 H10T 109.5 . . ?
C106 C105 C104 113.5(3) . . ?
C106 C105 H10E 108.9 . . ?
C104 C105 H10E 108.9 . . ?
C106 C105 H10F 108.9 . . ?
C104 C105 H10F 108.9 . . ?
H10E C105 H10F 107.7 . . ?
C105 C106 C107 111.6(3) . . ?
C105 C106 H10G 109.3 . . ?
C107 C106 H10G 109.3 . . ?
C105 C106 H10H 109.3 . . ?
C107 C106 H10H 109.3 . . ?
H10G C106 H10H 108.0 . . ?
N16 C107 C106 114.7(2) . . ?
N16 C107 H10C 108.6 . . ?
C106 C107 H10C 108.6 . . ?
N16 C107 H10D 108.6 . . ?
C106 C107 H10D 108.6 . . ?
H10C C107 H10D 107.6 . . ?
C109 C108 H10U 109.5 . . ?
C109 C108 H10V 109.5 . . ?
H10U C108 H10V 109.5 . . ?
C109 C108 H10W 109.5 . . ?
H10U C108 H10W 109.5 . . ?
H10V C108 H10W 109.5 . . ?
C108 C109 C110 112.9(3) . . ?
C108 C109 H10I 109.0 . . ?
C110 C109 H10I 109.0 . . ?
C108 C109 H10J 109.0 . . ?
C110 C109 H10J 109.0 . . ?
H10I C109 H10J 107.8 . . ?
C111 C110 C109 110.2(3) . . ?
C111 C110 H11C 109.6 . . ?
C109 C110 H11C 109.6 . . ?
C111 C110 H11D 109.6 . . ?
C109 C110 H11D 109.6 . . ?
H11C C110 H11D 108.1 . . ?
C110 C111 N16 115.5(2) . . ?
C110 C111 H11E 108.4 . . ?
N16 C111 H11E 108.4 . . ?
C110 C111 H11F 108.4 . . ?
N16 C111 H11F 108.4 . . ?
H11E C111 H11F 107.5 . . ?
C2 N1 C3 126.3(2) . . ?
C2 N1 H1 116.8 . . ?
C3 N1 H1 116.8 . . ?
C9 N2 N3 112.4(2) . . ?
C9 N2 H2 123.8 . . ?
N3 N2 H2 123.8 . . ?
C11 N3 N2 103.9(2) . . ?
C13 N4 C14 128.0(2) . . ?
C13 N4 H4A 116.0 . . ?
C14 N4 H4A 116.0 . . ?
C20 N5 N6 112.2(2) . . ?
C20 N5 H5A 123.9 . . ?
N6 N5 H5A 123.9 . . ?
C22 N6 N5 104.2(2) . . ?
C24 N7 C25 128.0(2) . . ?
C24 N7 H7A 116.0 . . ?
C25 N7 H7A 116.0 . . ?
C31 N8 N9 112.0(2) . . ?
C31 N8 H8A 124.0 . . ?
N9 N8 H8A 124.0 . . ?
C33 N9 N8 104.5(2) . . ?
C35 N10 C36 128.1(2) . . ?
C35 N10 H10 116.0 . . ?
C36 N10 H10 116.0 . . ?
C42 N11 N12 112.3(2) . . ?
C42 N11 H11A 123.9 . . ?
N12 N11 H11A 123.9 . . ?
C44 N12 N11 104.3(2) . . ?
C48 N13 C52 111.0(2) . . ?
C48 N13 C56 111.5(2) . . ?
C52 N13 C56 106.5(2) . . ?
C48 N13 C60 106.1(2) . . ?
C52 N13 C60 110.9(2) . . ?
C56 N13 C60 110.8(2) . . ?
C67 N14 C72 107.0(2) . . ?
C67 N14 C76 111.1(2) . . ?
C72 N14 C76 109.9(2) . . ?
C67 N14 C68 111.0(2) . . ?
C72 N14 C68 110.5(2) . . ?
C76 N14 C68 107.5(2) . . ?
C91 N15 C87 111.6(2) . . ?
C91 N15 C83 107.5(2) . . ?
C87 N15 C83 110.6(2) . . ?
C91 N15 C95 110.5(3) . . ?
C87 N15 C95 106.8(2) . . ?
C83 N15 C95 109.8(2) . . ?
C99 N16 C111 110.5(2) . . ?
C99 N16 C107 107.6(2) . . ?
C111 N16 C107 110.5(2) . . ?
C99 N16 C103 110.7(2) . . ?
C111 N16 C103 107.4(2) . . ?
C107 N16 C103 110.1(2) . . ?
H13A O13 H13B 106(3) . . ?
H14A O14 H14B 103(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
_geom_hbond_publ_flag
O14 H14A N12 0.93(3) 2.01(3) 2.900(3) 160(3) 1_645 yes
O14 H14B O8 0.92(3) 2.01(3) 2.890(3) 158(3) 3_655 yes
O13 H13B N9 1.02(3) 2.03(3) 3.028(3) 164(3) . yes
O13 H13A O10 0.97(3) 1.97(4) 2.815(3) 144(3) 3_665 yes
N8 H8A O10 0.88 1.91 2.776(3) 167.4 3_665 yes
N8 H8A O12 0.88 2.48 2.990(3) 117.3 3_665 yes
N1 H1 O5 0.88 2.05 2.881(3) 156.7 2_655 yes
N2 H2 O4 0.88 1.88 2.755(3) 173.2 1_565 yes
N4 H4A O1 0.88 2.11 2.923(3) 152.4 2_645 yes
N5 H5A O2 0.88 1.88 2.745(3) 166.1 1_445 yes
N5 H5A O3 0.88 2.47 2.978(3) 117.1 1_445 yes
N7 H7A O7 0.88 2.27 3.080(3) 152.4 3_655 yes
N10 H10 O11 0.88 2.16 2.982(3) 155.8 3_565 yes
N11 H11A O8 0.88 1.89 2.755(3) 166.1 3_565 yes
N11 H11A O8 0.88 1.89 2.755(3) 166.1 3_565 yes

_refine_diff_density_max         1.504
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.078

