# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SIL-SA-177
_database_code_depnum_ccdc_archive 'CCDC 2003785'
loop_
_audit_author_name
_audit_author_address
'Deborah de Alencar Simoni'
;State university of Campinas
Brazil
;

_audit_update_record             
;
2020-05-13 deposited with the CCDC.	2020-08-04 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H21 N O3'
_chemical_formula_sum            'C26 H21 N O3'
_chemical_formula_weight         395.44

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   14.9898(11)
_cell_length_b                   20.3897(14)
_cell_length_c                   6.6198(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2023.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    128
_cell_measurement_theta_min      32.35
_cell_measurement_theta_max      67.70

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.164
_exptl_absorpt_coefficient_mu    0.679
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6901
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker, 2010)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            13706
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.660
_diffrn_reflns_theta_max         68.906
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_point_group_measured_fraction_full 0.839
_reflns_number_total             3097
_reflns_number_gt                3078
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.538
_reflns_Friedel_fraction_max     0.639
_reflns_Friedel_fraction_full    0.649

_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       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXTL XT 2014/4 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_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)+(0.0451P)²+0.2601P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0057(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   .
_chemical_absolute_configuration .
_refine_ls_number_reflns         3097
_refine_ls_number_parameters     272
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0706
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.28809(8) 0.62780(6) 0.7941(2) 0.0363(3) Uani 1 1 d . . . . .
O2 O 0.23783(8) 0.52800(6) 0.7168(2) 0.0343(3) Uani 1 1 d . . . . .
O3 O 0.10351(8) 0.48945(6) 0.0840(2) 0.0384(3) Uani 1 1 d . . . . .
N1 N 0.29837(10) 0.69014(7) 0.6937(3) 0.0336(3) Uani 1 1 d . . . . .
C1 C 0.23728(10) 0.74446(7) 0.1856(3) 0.0284(4) Uani 1 1 d . . . . .
H1 H 0.2092 0.7063 0.1335 0.034 Uiso 1 1 calc R U . . .
C2 C 0.24294(11) 0.80036(8) 0.0663(4) 0.0361(4) Uani 1 1 d . . . . .
H2 H 0.2191 0.8003 -0.0667 0.043 Uiso 1 1 calc R U . . .
C3 C 0.28340(12) 0.85615(8) 0.1421(4) 0.0439(6) Uani 1 1 d . . . . .
H3 H 0.2871 0.8945 0.0611 0.053 Uiso 1 1 calc R U . . .
C4 C 0.31852(12) 0.85628(8) 0.3351(4) 0.0456(6) Uani 1 1 d . . . . .
H4 H 0.3460 0.8948 0.3864 0.055 Uiso 1 1 calc R U . . .
C5 C 0.31393(11) 0.80066(8) 0.4541(4) 0.0355(4) Uani 1 1 d . . . . .
H5 H 0.3390 0.8010 0.5859 0.043 Uiso 1 1 calc R U . . .
C6 C 0.27230(9) 0.74364(7) 0.3805(3) 0.0256(4) Uani 1 1 d . . . . .
C7 C 0.26774(9) 0.68537(7) 0.5135(3) 0.0233(4) Uani 1 1 d . . . . .
C8 C 0.25072(10) 0.58374(8) 0.6654(3) 0.0265(4) Uani 1 1 d . . . . .
C9 C 0.23073(9) 0.61775(7) 0.4666(3) 0.0204(3) Uani 1 1 d . . . . .
C10 C 0.12716(9) 0.61923(7) 0.4319(3) 0.0233(3) Uani 1 1 d . . . . .
H10 H 0.1162 0.6456 0.3071 0.028 Uiso 1 1 calc R U . . .
C11 C 0.07782(9) 0.65302(7) 0.6040(3) 0.0258(4) Uani 1 1 d . . . . .
C12 C 0.05813(10) 0.71985(8) 0.5891(3) 0.0340(4) Uani 1 1 d . . . . .
H12 H 0.0753 0.7436 0.4719 0.041 Uiso 1 1 calc R U . . .
C13 C 0.01361(12) 0.75180(8) 0.7446(4) 0.0420(5) Uani 1 1 d . . . . .
H13 H 0.0010 0.7973 0.7335 0.050 Uiso 1 1 calc R U . . .
C14 C -0.01255(11) 0.71778(9) 0.9158(4) 0.0402(5) Uani 1 1 d . . . . .
H14 H -0.0434 0.7397 1.0215 0.048 Uiso 1 1 calc R U . . .
C15 C 0.00663(11) 0.65173(9) 0.9313(3) 0.0353(4) Uani 1 1 d . . . . .
H15 H -0.0111 0.6282 1.0484 0.042 Uiso 1 1 calc R U . . .
C16 C 0.05156(11) 0.61950(8) 0.7772(3) 0.0293(4) Uani 1 1 d . . . . .
H16 H 0.0645 0.5741 0.7900 0.035 Uiso 1 1 calc R U . . .
C17 C 0.09185(10) 0.54935(8) 0.3907(3) 0.0285(4) Uani 1 1 d . . . . .
H17A H 0.0970 0.5230 0.5157 0.034 Uiso 1 1 calc R U . . .
H17B H 0.0279 0.5519 0.3544 0.034 Uiso 1 1 calc R U . . .
C18 C 0.14168(10) 0.51534(7) 0.2234(3) 0.0264(3) Uani 1 1 d . . . . .
C19 C 0.24216(10) 0.51472(7) 0.2435(3) 0.0248(3) Uani 1 1 d . . . . .
H19A H 0.2688 0.4975 0.1174 0.030 Uiso 1 1 calc R U . . .
H19B H 0.2593 0.4850 0.3552 0.030 Uiso 1 1 calc R U . . .
C20 C 0.27959(9) 0.58407(7) 0.2856(3) 0.0204(3) Uani 1 1 d . . . . .
H20 H 0.2667 0.6111 0.1631 0.024 Uiso 1 1 calc R U . . .
C21 C 0.38040(9) 0.58429(7) 0.3135(3) 0.0226(3) Uani 1 1 d . . . . .
C22 C 0.43203(10) 0.62619(7) 0.1957(3) 0.0272(4) Uani 1 1 d . . . . .
H22 H 0.4039 0.6537 0.0990 0.033 Uiso 1 1 calc R U . . .
C23 C 0.52420(11) 0.62835(8) 0.2178(4) 0.0354(4) Uani 1 1 d . . . . .
H23 H 0.5586 0.6573 0.1367 0.042 Uiso 1 1 calc R U . . .
C24 C 0.56578(11) 0.58844(10) 0.3572(3) 0.0390(5) Uani 1 1 d . . . . .
H24 H 0.6288 0.5899 0.3726 0.047 Uiso 1 1 calc R U . . .
C25 C 0.51543(12) 0.54632(10) 0.4742(4) 0.0410(5) Uani 1 1 d . . . . .
H25 H 0.5439 0.5188 0.5703 0.049 Uiso 1 1 calc R U . . .
C26 C 0.42337(11) 0.54404(9) 0.4521(3) 0.0326(4) Uani 1 1 d . . . . .
H26 H 0.3894 0.5146 0.5325 0.039 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.359(2) . ?
O1 N1 1.443(2) . ?
O2 C8 1.202(2) . ?
O3 C18 1.207(2) . ?
N1 C7 1.281(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.393(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.481(2) . ?
C7 C9 1.518(2) . ?
C8 C9 1.517(2) . ?
C9 C20 1.563(2) . ?
C9 C10 1.5696(19) . ?
C10 C11 1.523(2) . ?
C10 C17 1.544(2) . ?
C10 H10 1.0000 . ?
C11 C16 1.391(3) . ?
C11 C12 1.398(2) . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.505(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.512(2) . ?
C19 C20 1.5466(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.5223(19) . ?
C20 H20 1.0000 . ?
C21 C26 1.389(2) . ?
C21 C22 1.392(2) . ?
C22 C23 1.390(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
C8 O1 N1 109.72(14) . . ?
C7 N1 O1 108.89(13) . . ?
C2 C1 C6 120.88(17) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.25(19) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.40(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.55(17) . . ?
C1 C6 C7 122.90(14) . . ?
C5 C6 C7 118.55(17) . . ?
N1 C7 C6 118.43(14) . . ?
N1 C7 C9 112.97(15) . . ?
C6 C7 C9 128.60(15) . . ?
O2 C8 O1 120.94(17) . . ?
O2 C8 C9 130.21(16) . . ?
O1 C8 C9 108.85(13) . . ?
C8 C9 C7 99.52(13) . . ?
C8 C9 C20 111.81(12) . . ?
C7 C9 C20 112.62(12) . . ?
C8 C9 C10 109.33(13) . . ?
C7 C9 C10 111.95(11) . . ?
C20 C9 C10 111.08(13) . . ?
C11 C10 C17 112.53(13) . . ?
C11 C10 C9 112.30(13) . . ?
C17 C10 C9 110.32(12) . . ?
C11 C10 H10 107.1 . . ?
C17 C10 H10 107.1 . . ?
C9 C10 H10 107.1 . . ?
C16 C11 C12 118.51(16) . . ?
C16 C11 C10 122.10(14) . . ?
C12 C11 C10 119.39(17) . . ?
C13 C12 C11 120.43(19) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.47(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.37(18) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.54(19) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.68(15) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C18 C17 C10 112.65(13) . . ?
C18 C17 H17A 109.1 . . ?
C10 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C10 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
O3 C18 C17 121.92(14) . . ?
O3 C18 C19 122.40(16) . . ?
C17 C18 C19 115.68(15) . . ?
C18 C19 C20 111.69(12) . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C19 112.63(11) . . ?
C21 C20 C9 111.76(13) . . ?
C19 C20 C9 111.70(12) . . ?
C21 C20 H20 106.8 . . ?
C19 C20 H20 106.8 . . ?
C9 C20 H20 106.8 . . ?
C26 C21 C22 118.34(14) . . ?
C26 C21 C20 122.59(14) . . ?
C22 C21 C20 119.08(14) . . ?
C23 C22 C21 120.90(16) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.04(17) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 119.69(15) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 120.31(18) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.71(17) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.051


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SIL-SA380
_database_code_depnum_ccdc_archive 'CCDC 2003787'
loop_
_audit_author_name
_audit_author_address
'Deborah de Alencar Simoni'
;State university of Campinas
Brazil
;
#Added by publCIF



_audit_update_record             
;
2020-05-13 deposited with the CCDC.	2020-08-04 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H23 N O3'
_chemical_formula_sum            'C26 H23 N O3'
_chemical_formula_weight         397.45

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.0366(4)
_cell_length_b                   6.8796(2)
_cell_length_c                   26.6895(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.432(2)
_cell_angle_gamma                90
_cell_volume                     2022.83(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    142
_cell_measurement_theta_min      7.66
_cell_measurement_theta_max      38.11

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.680
_shelx_estimated_absorpt_T_min   0.738
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5342
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            24122
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.318
_diffrn_reflns_theta_max         68.975
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3673
_reflns_number_gt                3286
_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       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_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)+(0.0502P)²+0.6262P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3673
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.63365(9) 0.61013(13) 0.37735(4) 0.0408(3) Uani 1 1 d . . . . .
O2 O 0.69250(9) 0.57783(13) 0.45785(4) 0.0368(2) Uani 1 1 d . . . . .
O3 O 0.84588(9) -0.08263(13) 0.47208(4) 0.0362(2) Uani 1 1 d . . . . .
N1 N 0.62780(11) 0.49168(17) 0.33290(5) 0.0395(3) Uani 1 1 d . . . . .
C1 C 0.68004(11) 0.50529(18) 0.41686(5) 0.0292(3) Uani 1 1 d . . . . .
C2 C 0.70964(11) 0.30198(17) 0.39916(5) 0.0240(3) Uani 1 1 d . . . . .
C3 C 0.66901(11) 0.32214(18) 0.34445(5) 0.0270(3) Uani 1 1 d . . . . .
C4 C 0.67224(11) 0.1782(2) 0.30357(5) 0.0302(3) Uani 1 1 d . . . . .
C5 C 0.71675(13) -0.0093(2) 0.31118(5) 0.0349(3) Uani 1 1 d . . . . .
H5 H 0.7457 -0.0491 0.3438 0.042 Uiso 1 1 calc R U . . .
C6 C 0.71895(15) -0.1382(2) 0.27128(6) 0.0458(4) Uani 1 1 d . . . . .
H6 H 0.7497 -0.2661 0.2765 0.055 Uiso 1 1 calc R U . . .
C7 C 0.67622(16) -0.0802(3) 0.22376(6) 0.0540(5) Uani 1 1 d . . . . .
H7 H 0.6770 -0.1690 0.1965 0.065 Uiso 1 1 calc R U . . .
C8 C 0.63270(15) 0.1052(3) 0.21586(6) 0.0511(5) Uani 1 1 d . . . . .
H8 H 0.6043 0.1444 0.1831 0.061 Uiso 1 1 calc R U . . .
C9 C 0.63000(13) 0.2338(3) 0.25496(5) 0.0416(4) Uani 1 1 d . . . . .
H9 H 0.5994 0.3614 0.2492 0.050 Uiso 1 1 calc R U . . .
C10 C 0.63668(11) 0.14429(17) 0.42705(5) 0.0246(3) Uani 1 1 d . . . . .
H10 H 0.6601 0.0161 0.4129 0.029 Uiso 1 1 calc R U . . .
C11 C 0.67707(12) 0.13842(19) 0.48304(5) 0.0289(3) Uani 1 1 d . . . . .
H11A H 0.6562 0.2632 0.4989 0.035 Uiso 1 1 calc R U . . .
H11B H 0.6328 0.0336 0.4996 0.035 Uiso 1 1 calc R U . . .
C12 C 0.81326(12) 0.10318(18) 0.49102(5) 0.0302(3) Uani 1 1 d . . . . .
H12 H 0.8365 0.1085 0.5278 0.036 Uiso 1 1 calc R U . . .
C13 C 0.88703(12) 0.25341(19) 0.46415(5) 0.0288(3) Uani 1 1 d . . . . .
H13A H 0.9742 0.2197 0.4685 0.035 Uiso 1 1 calc R U . . .
H13B H 0.8757 0.3825 0.4796 0.035 Uiso 1 1 calc R U . . .
C14 C 0.84975(11) 0.26456(17) 0.40787(5) 0.0251(3) Uani 1 1 d . . . . .
H14 H 0.8658 0.1334 0.3935 0.030 Uiso 1 1 calc R U . . .
C15 C 0.50018(11) 0.16182(17) 0.41693(5) 0.0260(3) Uani 1 1 d . . . . .
C16 C 0.43838(12) 0.01788(19) 0.38912(5) 0.0322(3) Uani 1 1 d . . . . .
H16 H 0.4824 -0.0881 0.3764 0.039 Uiso 1 1 calc R U . . .
C17 C 0.31369(13) 0.0267(2) 0.37967(6) 0.0386(3) Uani 1 1 d . . . . .
H17 H 0.2730 -0.0739 0.3610 0.046 Uiso 1 1 calc R U . . .
C18 C 0.24827(12) 0.1809(2) 0.39719(5) 0.0370(3) Uani 1 1 d . . . . .
H18 H 0.1629 0.1876 0.3903 0.044 Uiso 1 1 calc R U . . .
C19 C 0.30794(13) 0.3248(2) 0.42470(5) 0.0375(3) Uani 1 1 d . . . . .
H19 H 0.2635 0.4316 0.4368 0.045 Uiso 1 1 calc R U . . .
C20 C 0.43271(12) 0.3151(2) 0.43495(5) 0.0335(3) Uani 1 1 d . . . . .
H20 H 0.4725 0.4143 0.4545 0.040 Uiso 1 1 calc R U . . .
C21 C 0.92274(11) 0.40974(18) 0.37896(5) 0.0276(3) Uani 1 1 d . . . . .
C22 C 0.95461(12) 0.5918(2) 0.39831(5) 0.0336(3) Uani 1 1 d . . . . .
H22 H 0.9338 0.6258 0.4312 0.040 Uiso 1 1 calc R U . . .
C23 C 1.01654(13) 0.7244(2) 0.37001(6) 0.0423(4) Uani 1 1 d . . . . .
H23 H 1.0366 0.8489 0.3835 0.051 Uiso 1 1 calc R U . . .
C24 C 1.04913(13) 0.6766(3) 0.32246(6) 0.0471(4) Uani 1 1 d . . . . .
H24 H 1.0918 0.7673 0.3033 0.056 Uiso 1 1 calc R U . . .
C25 C 1.01925(13) 0.4960(3) 0.30295(6) 0.0460(4) Uani 1 1 d . . . . .
H25 H 1.0417 0.4621 0.2703 0.055 Uiso 1 1 calc R U . . .
C26 C 0.95667(12) 0.3637(2) 0.33079(5) 0.0358(3) Uani 1 1 d . . . . .
H26 H 0.9365 0.2398 0.3169 0.043 Uiso 1 1 calc R U . . .
H3 H 0.7886(18) -0.167(3) 0.4778(7) 0.054 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3526(17) . ?
O1 N1 1.4376(16) . ?
O2 C1 1.2028(16) . ?
O3 C12 1.4286(16) . ?
O3 H3 0.88(2) . ?
N1 C3 1.2828(17) . ?
C1 C2 1.5181(17) . ?
C2 C3 1.5081(17) . ?
C2 C10 1.5656(16) . ?
C2 C14 1.5711(16) . ?
C3 C4 1.4755(19) . ?
C4 C5 1.390(2) . ?
C4 C9 1.4053(19) . ?
C5 C6 1.388(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.370(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.5193(17) . ?
C10 C11 1.5342(17) . ?
C10 H10 1.0000 . ?
C11 C12 1.5248(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5215(18) . ?
C12 H12 1.0000 . ?
C13 C14 1.5356(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C21 1.5218(17) . ?
C14 H14 1.0000 . ?
C15 C16 1.3915(19) . ?
C15 C20 1.3932(18) . ?
C16 C17 1.3856(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.3920(19) . ?
C21 C26 1.3969(19) . ?
C22 C23 1.390(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
C1 O1 N1 109.71(10) . . ?
C12 O3 H3 109.2(12) . . ?
C3 N1 O1 108.63(11) . . ?
O2 C1 O1 120.34(12) . . ?
O2 C1 C2 130.56(12) . . ?
O1 C1 C2 109.10(11) . . ?
C3 C2 C1 99.18(10) . . ?
C3 C2 C10 113.11(10) . . ?
C1 C2 C10 111.35(10) . . ?
C3 C2 C14 113.03(10) . . ?
C1 C2 C14 109.46(10) . . ?
C10 C2 C14 110.23(10) . . ?
N1 C3 C4 117.17(12) . . ?
N1 C3 C2 113.38(12) . . ?
C4 C3 C2 129.44(11) . . ?
C5 C4 C9 118.82(13) . . ?
C5 C4 C3 122.58(12) . . ?
C9 C4 C3 118.59(13) . . ?
C6 C5 C4 120.22(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 119.86(17) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C6 120.29(15) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 120.38(15) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C4 120.43(16) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C15 C10 C11 113.73(10) . . ?
C15 C10 C2 113.15(10) . . ?
C11 C10 C2 110.71(10) . . ?
C15 C10 H10 106.2 . . ?
C11 C10 H10 106.2 . . ?
C2 C10 H10 106.2 . . ?
C12 C11 C10 111.51(10) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
O3 C12 C13 106.73(11) . . ?
O3 C12 C11 111.11(10) . . ?
C13 C12 C11 112.15(11) . . ?
O3 C12 H12 108.9 . . ?
C13 C12 H12 108.9 . . ?
C11 C12 H12 108.9 . . ?
C12 C13 C14 112.04(10) . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C21 C14 C13 114.19(10) . . ?
C21 C14 C2 111.33(10) . . ?
C13 C14 C2 110.89(10) . . ?
C21 C14 H14 106.7 . . ?
C13 C14 H14 106.7 . . ?
C2 C14 H14 106.7 . . ?
C16 C15 C20 117.89(12) . . ?
C16 C15 C10 119.17(11) . . ?
C20 C15 C10 122.93(12) . . ?
C17 C16 C15 121.04(13) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.40(13) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.36(13) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 120.47(13) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.82(13) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C22 C21 C26 118.02(12) . . ?
C22 C21 C14 122.16(11) . . ?
C26 C21 C14 119.79(12) . . ?
C23 C22 C21 120.72(13) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.46(15) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.51(14) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 120.32(14) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.96(14) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 N1 C3 -0.20(14) . . . . ?
N1 O1 C1 O2 -179.93(11) . . . . ?
N1 O1 C1 C2 0.54(13) . . . . ?
O2 C1 C2 C3 179.92(13) . . . . ?
O1 C1 C2 C3 -0.62(12) . . . . ?
O2 C1 C2 C10 60.57(17) . . . . ?
O1 C1 C2 C10 -119.96(11) . . . . ?
O2 C1 C2 C14 -61.56(17) . . . . ?
O1 C1 C2 C14 117.90(11) . . . . ?
O1 N1 C3 C4 -179.25(10) . . . . ?
O1 N1 C3 C2 -0.23(14) . . . . ?
C1 C2 C3 N1 0.52(13) . . . . ?
C10 C2 C3 N1 118.55(12) . . . . ?
C14 C2 C3 N1 -115.29(12) . . . . ?
C1 C2 C3 C4 179.38(12) . . . . ?
C10 C2 C3 C4 -62.58(16) . . . . ?
C14 C2 C3 C4 63.57(16) . . . . ?
N1 C3 C4 C5 178.90(12) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
N1 C3 C4 C9 -0.31(18) . . . . ?
C2 C3 C4 C9 -179.13(12) . . . . ?
C9 C4 C5 C6 -0.07(19) . . . . ?
C3 C4 C5 C6 -179.28(12) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C9 -0.7(2) . . . . ?
C7 C8 C9 C4 0.3(2) . . . . ?
C5 C4 C9 C8 0.0(2) . . . . ?
C3 C4 C9 C8 179.27(12) . . . . ?
C3 C2 C10 C15 -47.81(14) . . . . ?
C1 C2 C10 C15 62.87(13) . . . . ?
C14 C2 C10 C15 -175.44(10) . . . . ?
C3 C2 C10 C11 -176.83(10) . . . . ?
C1 C2 C10 C11 -66.15(13) . . . . ?
C14 C2 C10 C11 55.54(12) . . . . ?
C15 C10 C11 C12 175.07(10) . . . . ?
C2 C10 C11 C12 -56.22(13) . . . . ?
C10 C11 C12 O3 -63.42(13) . . . . ?
C10 C11 C12 C13 55.94(14) . . . . ?
O3 C12 C13 C14 66.71(13) . . . . ?
C11 C12 C13 C14 -55.18(14) . . . . ?
C12 C13 C14 C21 -178.74(10) . . . . ?
C12 C13 C14 C2 54.52(13) . . . . ?
C3 C2 C14 C21 49.42(13) . . . . ?
C1 C2 C14 C21 -60.10(13) . . . . ?
C10 C2 C14 C21 177.10(10) . . . . ?
C3 C2 C14 C13 177.71(10) . . . . ?
C1 C2 C14 C13 68.20(12) . . . . ?
C10 C2 C14 C13 -54.61(13) . . . . ?
C11 C10 C15 C16 -120.80(12) . . . . ?
C2 C10 C15 C16 111.74(12) . . . . ?
C11 C10 C15 C20 58.20(16) . . . . ?
C2 C10 C15 C20 -69.25(15) . . . . ?
C20 C15 C16 C17 -0.04(19) . . . . ?
C10 C15 C16 C17 179.02(12) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C16 C17 C18 C19 -0.8(2) . . . . ?
C17 C18 C19 C20 -0.2(2) . . . . ?
C18 C19 C20 C15 1.1(2) . . . . ?
C16 C15 C20 C19 -0.98(19) . . . . ?
C10 C15 C20 C19 180.00(12) . . . . ?
C13 C14 C21 C22 -40.99(16) . . . . ?
C2 C14 C21 C22 85.52(14) . . . . ?
C13 C14 C21 C26 140.93(12) . . . . ?
C2 C14 C21 C26 -92.56(14) . . . . ?
C26 C21 C22 C23 1.1(2) . . . . ?
C14 C21 C22 C23 -177.05(13) . . . . ?
C21 C22 C23 C24 -1.0(2) . . . . ?
C22 C23 C24 C25 0.3(2) . . . . ?
C23 C24 C25 C26 0.2(2) . . . . ?
C24 C25 C26 C21 -0.1(2) . . . . ?
C22 C21 C26 C25 -0.6(2) . . . . ?
C14 C21 C26 C25 177.61(12) . . . . ?

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
C11 H11A O2 0.99 2.47 3.1037(16) 121.6 .
C13 H13B O2 0.99 2.47 3.0945(16) 120.9 .
O3 H3 O2 0.88(2) 2.10(2) 2.8965(14) 149.8(16) 1_545

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044


####################################################################### 
# 
# 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_SIL-sa-186_a
_database_code_depnum_ccdc_archive 'CCDC 2003786'
loop_
_audit_author_name
_audit_author_address
'Deborah de Alencar Simoni'
;State university of Campinas
Brazil
;
#Added by publCIF



_audit_update_record             
;
2020-05-13 deposited with the CCDC.	2020-08-04 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 N O3'
_chemical_formula_sum            'C27 H25 N O3'
_chemical_formula_weight         411.48

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'

_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                   33.6684(18)
_cell_length_b                   6.8422(3)
_cell_length_c                   19.7199(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.309(3)
_cell_angle_gamma                90
_cell_volume                     4420.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    120
_cell_measurement_theta_min      8.07
_cell_measurement_theta_max      37.60

_exptl_crystal_description       plate
_exptl_crystal_colour            'light orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    0.639
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6588
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            38811
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.697
_diffrn_reflns_theta_max         68.908
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7992
_reflns_number_gt                6879
_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       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_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)+(0.0537P)²+1.3995P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7992
_refine_ls_number_parameters     567
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.88751(4) 0.65449(16) 0.66221(7) 0.0511(3) Uani 1 1 d . . . . .
O2 O 0.82640(4) 0.60928(15) 0.59275(6) 0.0451(3) Uani 1 1 d . . . . .
O3 O 0.79159(3) -0.05444(14) 0.64172(6) 0.0353(2) Uani 1 1 d . . . . .
H3A H 0.7983(6) -0.141(3) 0.6104(11) 0.053 Uiso 1 1 d . U . . .
O4 O 0.60945(3) 1.10039(14) 0.75488(6) 0.0408(3) Uani 1 1 d . . . . .
O5 O 0.62784(3) 1.06998(14) 0.65417(6) 0.0352(2) Uani 1 1 d . . . . .
O6 O 0.68134(3) 0.40688(14) 0.65921(6) 0.0341(2) Uani 1 1 d . . . . .
H6A H 0.6620(6) 0.327(3) 0.6433(10) 0.051 Uiso 1 1 d . U . . .
N1 N 0.91739(4) 0.5413(2) 0.71008(9) 0.0497(4) Uani 1 1 d . . . . .
N2 N 0.60723(4) 0.97820(18) 0.81356(7) 0.0386(3) Uani 1 1 d . . . . .
C1 C 0.85473(5) 0.5429(2) 0.63540(8) 0.0350(3) Uani 1 1 d . . . . .
C2 C 0.86117(4) 0.34000(19) 0.66775(7) 0.0256(3) Uani 1 1 d . . . . .
C3 C 0.90330(4) 0.3672(2) 0.71352(8) 0.0321(3) Uani 1 1 d . . . . .
C4 C 0.92951(4) 0.2253(2) 0.75898(8) 0.0362(3) Uani 1 1 d . . . . .
C5 C 0.96971(5) 0.2808(3) 0.79052(9) 0.0549(5) Uani 1 1 d . . . . .
H5 H 0.9792 0.4070 0.7820 0.066 Uiso 1 1 calc R U . . .
C6 C 0.99515(6) 0.1540(4) 0.83340(11) 0.0704(7) Uani 1 1 d . . . . .
H6 H 1.0222 0.1928 0.8547 0.084 Uiso 1 1 calc R U . . .
C7 C 0.98179(7) -0.0290(4) 0.84582(10) 0.0713(7) Uani 1 1 d . . . . .
H7 H 0.9998 -0.1163 0.8754 0.086 Uiso 1 1 calc R U . . .
C8 C 0.94186(6) -0.0888(3) 0.81550(9) 0.0579(5) Uani 1 1 d . . . . .
H8 H 0.9326 -0.2152 0.8246 0.069 Uiso 1 1 calc R U . . .
C9 C 0.91597(5) 0.0403(2) 0.77182(8) 0.0406(4) Uani 1 1 d . . . . .
H9 H 0.8889 0.0015 0.7506 0.049 Uiso 1 1 calc R U . . .
C10 C 0.82759(4) 0.29885(19) 0.70978(7) 0.0249(3) Uani 1 1 d . . . . .
H10 H 0.8338 0.1672 0.7317 0.030 Uiso 1 1 calc R U . . .
C11 C 0.82998(4) 0.4431(2) 0.76911(7) 0.0268(3) Uani 1 1 d . . . . .
C12 C 0.81167(4) 0.6269(2) 0.75837(7) 0.0301(3) Uani 1 1 d . . . . .
H12 H 0.7967 0.6623 0.7131 0.036 Uiso 1 1 calc R U . . .
C13 C 0.81505(5) 0.7585(2) 0.81279(8) 0.0370(3) Uani 1 1 d . . . . .
H13 H 0.8024 0.8832 0.8046 0.044 Uiso 1 1 calc R U . . .
C14 C 0.83674(5) 0.7092(3) 0.87899(9) 0.0444(4) Uani 1 1 d . . . . .
H14 H 0.8391 0.7996 0.9163 0.053 Uiso 1 1 calc R U . . .
C15 C 0.85491(5) 0.5272(3) 0.89046(8) 0.0459(4) Uani 1 1 d . . . . .
H15 H 0.8698 0.4924 0.9358 0.055 Uiso 1 1 calc R U . . .
C16 C 0.85146(5) 0.3954(2) 0.83601(8) 0.0365(3) Uani 1 1 d . . . . .
H16 H 0.8640 0.2706 0.8446 0.044 Uiso 1 1 calc R U . . .
C17 C 0.78529(4) 0.2831(2) 0.65999(7) 0.0286(3) Uani 1 1 d . . . . .
H17A H 0.7648 0.2519 0.6872 0.034 Uiso 1 1 calc R U . . .
H17B H 0.7779 0.4110 0.6370 0.034 Uiso 1 1 calc R U . . .
C18 C 0.78377(4) 0.12679(19) 0.60432(7) 0.0275(3) Uani 1 1 d . . . . .
C19 C 0.81676(4) 0.1635(2) 0.56390(7) 0.0271(3) Uani 1 1 d . . . . .
H19A H 0.8104 0.2861 0.5369 0.033 Uiso 1 1 calc R U . . .
H19B H 0.8163 0.0555 0.5303 0.033 Uiso 1 1 calc R U . . .
C20 C 0.85970(4) 0.17905(18) 0.61102(7) 0.0244(3) Uani 1 1 d . . . . .
H20 H 0.8654 0.0517 0.6362 0.029 Uiso 1 1 calc R U . . .
C21 C 0.89234(4) 0.20498(19) 0.56976(7) 0.0270(3) Uani 1 1 d . . . . .
C22 C 0.92386(5) 0.0712(2) 0.57773(8) 0.0378(3) Uani 1 1 d . . . . .
H22 H 0.9254 -0.0330 0.6101 0.045 Uiso 1 1 calc R U . . .
C23 C 0.95332(6) 0.0877(3) 0.53886(10) 0.0528(5) Uani 1 1 d . . . . .
H23 H 0.9748 -0.0055 0.5448 0.063 Uiso 1 1 calc R U . . .
C24 C 0.95173(5) 0.2377(3) 0.49184(9) 0.0493(4) Uani 1 1 d . . . . .
H24 H 0.9718 0.2476 0.4651 0.059 Uiso 1 1 calc R U . . .
C25 C 0.92092(5) 0.3728(2) 0.48397(8) 0.0420(4) Uani 1 1 d . . . . .
H25 H 0.9199 0.4783 0.4523 0.050 Uiso 1 1 calc R U . . .
C26 C 0.89127(5) 0.3559(2) 0.52220(8) 0.0362(3) Uani 1 1 d . . . . .
H26 H 0.8698 0.4493 0.5158 0.043 Uiso 1 1 calc R U . . .
C27 C 0.74181(4) 0.1182(2) 0.55498(8) 0.0353(3) Uani 1 1 d . . . . .
H27A H 0.7361 0.2428 0.5302 0.053 Uiso 1 1 calc R U . . .
H27B H 0.7211 0.0939 0.5817 0.053 Uiso 1 1 calc R U . . .
H27C H 0.7412 0.0123 0.5213 0.053 Uiso 1 1 calc R U . . .
C28 C 0.62411(4) 0.99566(19) 0.70787(8) 0.0286(3) Uani 1 1 d . . . . .
C29 C 0.63420(4) 0.79001(18) 0.73577(7) 0.0238(3) Uani 1 1 d . . . . .
C30 C 0.62045(4) 0.80708(19) 0.80319(7) 0.0276(3) Uani 1 1 d . . . . .
C31 C 0.61946(4) 0.6564(2) 0.85659(7) 0.0297(3) Uani 1 1 d . . . . .
C32 C 0.59571(5) 0.6909(3) 0.90507(8) 0.0397(4) Uani 1 1 d . . . . .
H32 H 0.5798 0.8067 0.9021 0.048 Uiso 1 1 calc R U . . .
C33 C 0.59541(5) 0.5559(3) 0.95736(8) 0.0487(5) Uani 1 1 d . . . . .
H33 H 0.5790 0.5792 0.9898 0.058 Uiso 1 1 calc R U . . .
C34 C 0.61864(6) 0.3882(3) 0.96291(9) 0.0498(4) Uani 1 1 d . . . . .
H34 H 0.6189 0.2987 0.9998 0.060 Uiso 1 1 calc R U . . .
C35 C 0.64151(5) 0.3510(3) 0.91489(9) 0.0445(4) Uani 1 1 d . . . . .
H35 H 0.6572 0.2346 0.9182 0.053 Uiso 1 1 calc R U . . .
C36 C 0.64167(5) 0.4836(2) 0.86154(8) 0.0353(3) Uani 1 1 d . . . . .
H36 H 0.6572 0.4558 0.8280 0.042 Uiso 1 1 calc R U . . .
C37 C 0.60982(4) 0.63100(18) 0.68649(7) 0.0246(3) Uani 1 1 d . . . . .
H37 H 0.6170 0.5021 0.7100 0.030 Uiso 1 1 calc R U . . .
C38 C 0.56386(4) 0.6543(2) 0.67533(7) 0.0278(3) Uani 1 1 d . . . . .
C39 C 0.54270(4) 0.8037(2) 0.63428(8) 0.0365(3) Uani 1 1 d . . . . .
H39 H 0.5572 0.8947 0.6128 0.044 Uiso 1 1 calc R U . . .
C40 C 0.50071(5) 0.8210(3) 0.62446(9) 0.0429(4) Uani 1 1 d . . . . .
H40 H 0.4868 0.9243 0.5966 0.051 Uiso 1 1 calc R U . . .
C41 C 0.47901(4) 0.6892(3) 0.65482(9) 0.0421(4) Uani 1 1 d . . . . .
H41 H 0.4502 0.7005 0.6476 0.050 Uiso 1 1 calc R U . . .
C42 C 0.49948(5) 0.5411(2) 0.69573(9) 0.0422(4) Uani 1 1 d . . . . .
H42 H 0.4847 0.4506 0.7171 0.051 Uiso 1 1 calc R U . . .
C43 C 0.54157(4) 0.5233(2) 0.70600(8) 0.0348(3) Uani 1 1 d . . . . .
H43 H 0.5553 0.4204 0.7343 0.042 Uiso 1 1 calc R U . . .
C44 C 0.62357(4) 0.62324(19) 0.61755(7) 0.0266(3) Uani 1 1 d . . . . .
H44A H 0.6089 0.5156 0.5887 0.032 Uiso 1 1 calc R U . . .
H44B H 0.6157 0.7470 0.5919 0.032 Uiso 1 1 calc R U . . .
C45 C 0.66947(4) 0.59251(18) 0.62672(7) 0.0262(3) Uani 1 1 d . . . . .
C46 C 0.69326(4) 0.74561(19) 0.67606(7) 0.0259(3) Uani 1 1 d . . . . .
H46A H 0.6885 0.8756 0.6537 0.031 Uiso 1 1 calc R U . . .
H46B H 0.7228 0.7167 0.6841 0.031 Uiso 1 1 calc R U . . .
C47 C 0.68136(4) 0.75316(18) 0.74656(7) 0.0239(3) Uani 1 1 d . . . . .
H47 H 0.6869 0.6204 0.7679 0.029 Uiso 1 1 calc R U . . .
C48 C 0.70693(4) 0.8969(2) 0.79737(7) 0.0260(3) Uani 1 1 d . . . . .
C49 C 0.71578(4) 1.0829(2) 0.77604(7) 0.0291(3) Uani 1 1 d . . . . .
H49 H 0.7052 1.1220 0.7291 0.035 Uiso 1 1 calc R U . . .
C50 C 0.73981(4) 1.2117(2) 0.82227(8) 0.0344(3) Uani 1 1 d . . . . .
H50 H 0.7455 1.3380 0.8069 0.041 Uiso 1 1 calc R U . . .
C51 C 0.75543(5) 1.1567(2) 0.89059(8) 0.0405(4) Uani 1 1 d . . . . .
H51 H 0.7721 1.2445 0.9222 0.049 Uiso 1 1 calc R U . . .
C52 C 0.74672(5) 0.9733(3) 0.91271(8) 0.0417(4) Uani 1 1 d . . . . .
H52 H 0.7573 0.9353 0.9597 0.050 Uiso 1 1 calc R U . . .
C53 C 0.72258(4) 0.8445(2) 0.86652(8) 0.0340(3) Uani 1 1 d . . . . .
H53 H 0.7167 0.7191 0.8823 0.041 Uiso 1 1 calc R U . . .
C54 C 0.68131(4) 0.6020(2) 0.55664(8) 0.0338(3) Uani 1 1 d . . . . .
H54A H 0.6668 0.4998 0.5259 0.051 Uiso 1 1 calc R U . . .
H54B H 0.7108 0.5819 0.5637 0.051 Uiso 1 1 calc R U . . .
H54C H 0.6740 0.7303 0.5354 0.051 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.346(2) . ?
O1 N1 1.437(2) . ?
O2 C1 1.206(2) . ?
O3 C18 1.4357(16) . ?
O3 H3A 0.92(2) . ?
O4 C28 1.3517(18) . ?
O4 N2 1.4435(17) . ?
O5 C28 1.2069(17) . ?
O6 C45 1.4373(16) . ?
O6 H6A 0.85(2) . ?
N1 C3 1.290(2) . ?
N2 C30 1.2856(18) . ?
C1 C2 1.5225(19) . ?
C2 C3 1.507(2) . ?
C2 C20 1.5624(18) . ?
C2 C10 1.5734(17) . ?
C3 C4 1.470(2) . ?
C4 C9 1.388(2) . ?
C4 C5 1.406(2) . ?
C5 C6 1.367(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.371(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.5185(19) . ?
C10 C17 1.5362(18) . ?
C10 H10 1.0000 . ?
C11 C16 1.389(2) . ?
C11 C12 1.3954(19) . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.5248(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C27 1.521(2) . ?
C18 C19 1.5297(18) . ?
C19 C20 1.5320(18) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.5207(18) . ?
C20 H20 1.0000 . ?
C21 C22 1.383(2) . ?
C21 C26 1.390(2) . ?
C22 C23 1.391(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.376(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.371(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.5205(18) . ?
C29 C30 1.5094(18) . ?
C29 C37 1.5604(18) . ?
C29 C47 1.5730(17) . ?
C30 C31 1.479(2) . ?
C31 C36 1.391(2) . ?
C31 C32 1.400(2) . ?
C32 C33 1.386(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.379(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.375(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.390(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.5204(18) . ?
C37 C44 1.5345(18) . ?
C37 H37 1.0000 . ?
C38 C43 1.393(2) . ?
C38 C39 1.394(2) . ?
C39 C40 1.387(2) . ?
C39 H39 0.9500 . ?
C40 C41 1.381(2) . ?
C40 H40 0.9500 . ?
C41 C42 1.377(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.390(2) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 C45 1.5286(18) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C54 1.5254(19) . ?
C45 C46 1.5255(18) . ?
C46 C47 1.5337(18) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.5214(18) . ?
C47 H47 1.0000 . ?
C48 C53 1.391(2) . ?
C48 C49 1.3941(19) . ?
C49 C50 1.387(2) . ?
C49 H49 0.9500 . ?
C50 C51 1.381(2) . ?
C50 H50 0.9500 . ?
C51 C52 1.382(2) . ?
C51 H51 0.9500 . ?
C52 C53 1.388(2) . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?

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
C1 O1 N1 109.83(11) . . ?
C18 O3 H3A 104.9(12) . . ?
C28 O4 N2 109.71(10) . . ?
C45 O6 H6A 107.1(13) . . ?
C3 N1 O1 108.77(13) . . ?
C30 N2 O4 108.43(11) . . ?
O2 C1 O1 120.40(14) . . ?
O2 C1 C2 130.46(15) . . ?
O1 C1 C2 109.14(14) . . ?
C3 C2 C1 99.30(12) . . ?
C3 C2 C20 112.71(11) . . ?
C1 C2 C20 111.40(11) . . ?
C3 C2 C10 113.45(11) . . ?
C1 C2 C10 109.50(10) . . ?
C20 C2 C10 110.06(10) . . ?
N1 C3 C4 117.76(14) . . ?
N1 C3 C2 112.93(14) . . ?
C4 C3 C2 129.31(13) . . ?
C9 C4 C5 119.27(16) . . ?
C9 C4 C3 122.50(13) . . ?
C5 C4 C3 118.23(16) . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.36(19) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C8 120.84(19) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C4 C9 C8 120.42(17) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C17 114.52(11) . . ?
C11 C10 C2 111.88(11) . . ?
C17 C10 C2 110.41(10) . . ?
C11 C10 H10 106.5 . . ?
C17 C10 H10 106.5 . . ?
C2 C10 H10 106.5 . . ?
C16 C11 C12 118.08(13) . . ?
C16 C11 C10 120.19(12) . . ?
C12 C11 C10 121.71(12) . . ?
C13 C12 C11 120.92(14) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.25(14) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.46(15) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.26(15) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 121.02(14) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C18 C17 C10 112.46(11) . . ?
C18 C17 H17A 109.1 . . ?
C10 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C10 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
O3 C18 C27 109.19(11) . . ?
O3 C18 C17 105.32(11) . . ?
C27 C18 C17 111.11(11) . . ?
O3 C18 C19 109.88(11) . . ?
C27 C18 C19 110.61(11) . . ?
C17 C18 C19 110.60(11) . . ?
C18 C19 C20 113.11(11) . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 112.39(11) . . ?
C21 C20 C2 113.16(11) . . ?
C19 C20 C2 110.67(10) . . ?
C21 C20 H20 106.7 . . ?
C19 C20 H20 106.7 . . ?
C2 C20 H20 106.7 . . ?
C22 C21 C26 117.95(13) . . ?
C22 C21 C20 119.47(12) . . ?
C26 C21 C20 122.55(12) . . ?
C21 C22 C23 120.63(15) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.67(16) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.36(15) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.17(15) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 121.23(14) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
C18 C27 H27A 109.5 . . ?
C18 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C18 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O5 C28 O4 120.43(12) . . ?
O5 C28 C29 130.37(13) . . ?
O4 C28 C29 109.20(12) . . ?
C30 C29 C28 99.14(10) . . ?
C30 C29 C37 112.24(10) . . ?
C28 C29 C37 112.23(11) . . ?
C30 C29 C47 113.44(11) . . ?
C28 C29 C47 109.37(10) . . ?
C37 C29 C47 110.02(10) . . ?
N2 C30 C31 117.11(13) . . ?
N2 C30 C29 113.47(12) . . ?
C31 C30 C29 129.41(12) . . ?
C36 C31 C32 118.54(14) . . ?
C36 C31 C30 122.85(12) . . ?
C32 C31 C30 118.60(13) . . ?
C33 C32 C31 119.91(16) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.82(16) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C35 C34 C33 119.80(16) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.05(17) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 C31 120.81(15) . . ?
C35 C36 H36 119.6 . . ?
C31 C36 H36 119.6 . . ?
C38 C37 C44 112.33(11) . . ?
C38 C37 C29 112.90(11) . . ?
C44 C37 C29 110.68(10) . . ?
C38 C37 H37 106.8 . . ?
C44 C37 H37 106.8 . . ?
C29 C37 H37 106.8 . . ?
C43 C38 C39 118.00(13) . . ?
C43 C38 C37 120.13(12) . . ?
C39 C38 C37 121.87(12) . . ?
C40 C39 C38 120.80(14) . . ?
C40 C39 H39 119.6 . . ?
C38 C39 H39 119.6 . . ?
C41 C40 C39 120.50(15) . . ?
C41 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?
C42 C41 C40 119.41(14) . . ?
C42 C41 H41 120.3 . . ?
C40 C41 H41 120.3 . . ?
C41 C42 C43 120.40(14) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C42 C43 C38 120.88(14) . . ?
C42 C43 H43 119.6 . . ?
C38 C43 H43 119.6 . . ?
C45 C44 C37 113.76(11) . . ?
C45 C44 H44A 108.8 . . ?
C37 C44 H44A 108.8 . . ?
C45 C44 H44B 108.8 . . ?
C37 C44 H44B 108.8 . . ?
H44A C44 H44B 107.7 . . ?
O6 C45 C54 109.72(11) . . ?
O6 C45 C46 105.73(11) . . ?
C54 C45 C46 109.90(11) . . ?
O6 C45 C44 110.14(10) . . ?
C54 C45 C44 110.80(11) . . ?
C46 C45 C44 110.44(11) . . ?
C45 C46 C47 113.14(10) . . ?
C45 C46 H46A 109.0 . . ?
C47 C46 H46A 109.0 . . ?
C45 C46 H46B 109.0 . . ?
C47 C46 H46B 109.0 . . ?
H46A C46 H46B 107.8 . . ?
C48 C47 C46 113.10(10) . . ?
C48 C47 C29 112.71(10) . . ?
C46 C47 C29 110.42(10) . . ?
C48 C47 H47 106.7 . . ?
C46 C47 H47 106.7 . . ?
C29 C47 H47 106.7 . . ?
C53 C48 C49 118.15(13) . . ?
C53 C48 C47 120.57(12) . . ?
C49 C48 C47 121.28(12) . . ?
C50 C49 C48 120.99(13) . . ?
C50 C49 H49 119.5 . . ?
C48 C49 H49 119.5 . . ?
C51 C50 C49 120.12(14) . . ?
C51 C50 H50 119.9 . . ?
C49 C50 H50 119.9 . . ?
C50 C51 C52 119.63(14) . . ?
C50 C51 H51 120.2 . . ?
C52 C51 H51 120.2 . . ?
C51 C52 C53 120.29(14) . . ?
C51 C52 H52 119.9 . . ?
C53 C52 H52 119.9 . . ?
C52 C53 C48 120.83(14) . . ?
C52 C53 H53 119.6 . . ?
C48 C53 H53 119.6 . . ?
C45 C54 H54A 109.5 . . ?
C45 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C45 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.038


