# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1850228'
loop_
_audit_author_name
_audit_author_address
'Tong guanghu'
;Xi'an Jiaotong University
China
;
_audit_update_record             
;
2018-06-19 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_audit_creation_date             2018-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C28 H46 O5 Si'
_chemical_formula_sum            'C28 H46 O5 Si'
_chemical_formula_weight         490.74
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   21.082(6)
_cell_length_b                   11.132(3)
_cell_length_c                   25.377(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.904(6)
_cell_angle_gamma                90
_cell_volume                     5942(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6223
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.00
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9762
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.316
_exptl_crystal_size_min          0.218
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21762
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.785
_diffrn_reflns_theta_max         24.785
_diffrn_reflns_theta_min         1.609
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3680
_reflns_number_total             5063
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5063
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1214P)²+7.3120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2074
_refine_ls_wR_factor_ref         0.2286
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C6-C5
 1.62 with sigma of 0.01
3. Rigid bond restraints
 C4, C5, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C4 \\sim C5 \\sim C6: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02
5.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C12(H12), C14(H14), C16(H16)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C26(H26A,H26B)
5.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C24(H24), C25(H25)
5.d X=CH2 refined with riding coordinates:
 C27(H27A,H27B)
5.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C7(H7A,
 H7B,H7C), C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C29(H29A,
 H29B,H29C)
5.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20175(10) 0.4277(2) 0.35157(9) 0.0655(6) Uani 1 1 d . . . . .
O2 O 0.36246(11) 0.4277(2) 0.36337(8) 0.0718(7) Uani 1 1 d . . . . .
O3 O 0.44088(9) 0.4112(2) 0.42757(8) 0.0601(6) Uani 1 1 d . . . . .
O4 O 0.45755(10) 0.2727(2) 0.53684(9) 0.0698(7) Uani 1 1 d . . . . .
H4 H 0.4872 0.2304 0.5484 0.105 Uiso 1 1 calc GR . . . .
O5 O 0.42025(17) -0.1500(3) 0.44956(17) 0.1343(15) Uani 1 1 d . . . . .
Si1 Si 0.16306(5) 0.46377(9) 0.29548(4) 0.0686(3) Uani 1 1 d . . . . .
C1 C 0.1768(3) 0.4443(8) 0.18414(19) 0.163(3) Uani 1 1 d . . . . .
H1A H 0.1642 0.5266 0.1790 0.245 Uiso 1 1 calc GR . . . .
H1B H 0.1397 0.3941 0.1824 0.245 Uiso 1 1 calc GR . . . .
H1C H 0.2040 0.4210 0.1571 0.245 Uiso 1 1 calc GR . . . .
C2 C 0.2130(2) 0.4304(5) 0.23899(16) 0.0999(15) Uani 1 1 d . . . . .
H2 H 0.2246 0.3453 0.2422 0.120 Uiso 1 1 calc R . . . .
C3 C 0.2758(3) 0.5007(7) 0.2415(2) 0.145(2) Uani 1 1 d . . . . .
H3A H 0.3027 0.4693 0.2157 0.218 Uiso 1 1 calc GR . . . .
H3B H 0.2968 0.4928 0.2761 0.218 Uiso 1 1 calc GR . . . .
H3C H 0.2672 0.5840 0.2342 0.218 Uiso 1 1 calc GR . . . .
C4 C 0.1012(5) 0.6833(7) 0.2634(3) 0.226(4) Uani 1 1 d . U . . .
H4A H 0.0609 0.6432 0.2628 0.339 Uiso 1 1 calc GR . . . .
H4B H 0.1176 0.6785 0.2291 0.339 Uiso 1 1 calc GR . . . .
H4C H 0.0959 0.7661 0.2728 0.339 Uiso 1 1 calc GR . . . .
C5 C 0.1462(4) 0.6251(5) 0.3028(3) 0.171(3) Uani 1 1 d D U . . .
H5 H 0.1842 0.6514 0.2858 0.206 Uiso 1 1 calc R . . . .
C6 C 0.1642(6) 0.6838(6) 0.3531(3) 0.252(5) Uani 1 1 d D U . . .
H6A H 0.1618 0.7694 0.3487 0.377 Uiso 1 1 calc GR . . . .
H6B H 0.2069 0.6615 0.3647 0.377 Uiso 1 1 calc GR . . . .
H6C H 0.1357 0.6591 0.3790 0.377 Uiso 1 1 calc GR . . . .
C7 C 0.0990(2) 0.2406(5) 0.2791(2) 0.1208(18) Uani 1 1 d . . . . .
H7A H 0.1192 0.2080 0.3110 0.181 Uiso 1 1 calc GR . . . .
H7B H 0.1259 0.2287 0.2505 0.181 Uiso 1 1 calc GR . . . .
H7C H 0.0591 0.2007 0.2712 0.181 Uiso 1 1 calc GR . . . .
C8 C 0.08759(17) 0.3735(5) 0.28627(14) 0.0855(13) Uani 1 1 d . . . . .
H8 H 0.0652 0.4020 0.2535 0.103 Uiso 1 1 calc R . . . .
C9 C 0.0427(3) 0.3928(7) 0.3301(2) 0.148(3) Uani 1 1 d . . . . .
H9A H 0.0032 0.3526 0.3211 0.223 Uiso 1 1 calc GR . . . .
H9B H 0.0351 0.4772 0.3342 0.223 Uiso 1 1 calc GR . . . .
H9C H 0.0616 0.3608 0.3626 0.223 Uiso 1 1 calc GR . . . .
C11 C 0.23959(14) 0.3260(3) 0.36367(12) 0.0580(8) Uani 1 1 d . . . . .
H11A H 0.2665 0.3099 0.3350 0.070 Uiso 1 1 calc R . . . .
H11B H 0.2126 0.2566 0.3679 0.070 Uiso 1 1 calc R . . . .
C12 C 0.28053(13) 0.3477(3) 0.41425(11) 0.0511(7) Uani 1 1 d . . . . .
H12 H 0.2525 0.3711 0.4418 0.061 Uiso 1 1 calc R . . . .
C13 C 0.31886(14) 0.2398(3) 0.43397(12) 0.0547(7) Uani 1 1 d . . . . .
H13A H 0.3414 0.2041 0.4058 0.066 Uiso 1 1 calc R . . . .
H13B H 0.2917 0.1795 0.4484 0.066 Uiso 1 1 calc R . . . .
C14 C 0.36543(13) 0.2925(2) 0.47709(11) 0.0473(7) Uani 1 1 d . . . . .
H14 H 0.3400 0.3091 0.5072 0.057 Uiso 1 1 calc R . . . .
C15 C 0.38380(13) 0.4178(3) 0.45535(11) 0.0484(7) Uani 1 1 d . . . . .
C16 C 0.33138(14) 0.4449(3) 0.41095(11) 0.0532(7) Uani 1 1 d . . . . .
H16 H 0.3139 0.5261 0.4137 0.064 Uiso 1 1 calc R . . . .
C17 C 0.4667(2) 0.3776(5) 0.33931(17) 0.1050(15) Uani 1 1 d . . . . .
H17A H 0.5112 0.3907 0.3479 0.157 Uiso 1 1 calc GR . . . .
H17B H 0.4564 0.3994 0.3031 0.157 Uiso 1 1 calc GR . . . .
H17C H 0.4569 0.2943 0.3443 0.157 Uiso 1 1 calc GR . . . .
C18 C 0.42854(17) 0.4532(3) 0.37472(13) 0.0689(9) Uani 1 1 d . . . . .
C19 C 0.4414(2) 0.5858(4) 0.37027(16) 0.0902(13) Uani 1 1 d . . . . .
H19A H 0.4122 0.6297 0.3904 0.135 Uiso 1 1 calc GR . . . .
H19B H 0.4360 0.6097 0.3339 0.135 Uiso 1 1 calc GR . . . .
H19C H 0.4841 0.6026 0.3837 0.135 Uiso 1 1 calc GR . . . .
C20 C 0.41857(13) 0.2065(3) 0.49824(11) 0.0514(7) Uani 1 1 d . . . . .
C21 C 0.45797(15) 0.1613(3) 0.45563(13) 0.0642(9) Uani 1 1 d . . . . .
H21 H 0.4845 0.2149 0.4397 0.077 Uiso 1 1 calc R . . . .
C22 C 0.45652(18) 0.0469(4) 0.43956(16) 0.0802(12) Uani 1 1 d . . . . .
H22 H 0.4799 0.0248 0.4113 0.096 Uiso 1 1 calc R . . . .
C23 C 0.4190(2) -0.0453(4) 0.4652(2) 0.0898(14) Uani 1 1 d . . . . .
C24 C 0.38513(18) -0.0080(3) 0.50967(19) 0.0816(12) Uani 1 1 d . . . . .
H24 H 0.3617 -0.0640 0.5274 0.098 Uiso 1 1 calc R . . . .
C25 C 0.38679(15) 0.1055(3) 0.52582(14) 0.0627(8) Uani 1 1 d . . . . .
H25 H 0.3669 0.1239 0.5564 0.075 Uiso 1 1 calc R . . . .
C26 C 0.39523(15) 0.5146(3) 0.49879(12) 0.0587(8) Uani 1 1 d . . . . .
H26A H 0.4341 0.4944 0.5195 0.070 Uiso 1 1 calc R . . . .
H26B H 0.4023 0.5908 0.4816 0.070 Uiso 1 1 calc R . . . .
C27 C 0.3500(3) 0.4847(4) 0.58566(17) 0.0984(14) Uani 1 1 d . . . . .
H27A H 0.3189 0.4989 0.6091 0.118 Uiso 1 1 calc R . . . .
H27B H 0.3854 0.4383 0.5961 0.118 Uiso 1 1 calc R . . . .
C28 C 0.34382(17) 0.5319(3) 0.53589(14) 0.0679(9) Uani 1 1 d . . . . .
C29 C 0.2891(2) 0.6046(5) 0.5186(2) 0.1172(18) Uani 1 1 d . . . . .
H29A H 0.2615 0.6126 0.5470 0.176 Uiso 1 1 calc GR . . . .
H29B H 0.2664 0.5666 0.4890 0.176 Uiso 1 1 calc GR . . . .
H29C H 0.3031 0.6827 0.5083 0.176 Uiso 1 1 calc GR . . . .


_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 Si1 1.642(2) . ?
O1 C11 1.406(4) . ?
O2 C16 1.425(4) . ?
O2 C18 1.432(4) . ?
O3 C15 1.437(4) . ?
O3 C18 1.428(4) . ?
O4 C20 1.439(3) . ?
O5 C23 1.232(5) . ?
Si1 C2 1.873(5) . ?
Si1 C5 1.842(6) . ?
Si1 C8 1.883(4) . ?
C1 C2 1.549(6) . ?
C2 C3 1.537(7) . ?
C4 C5 1.480(8) . ?
C5 C6 1.462(7) . ?
C7 C8 1.512(7) . ?
C8 C9 1.523(6) . ?
C11 C12 1.517(4) . ?
C12 C13 1.514(4) . ?
C12 C16 1.530(4) . ?
C13 C14 1.536(4) . ?
C14 C15 1.559(4) . ?
C14 C20 1.542(4) . ?
C15 C16 1.553(4) . ?
C15 C26 1.548(4) . ?
C17 C18 1.504(6) . ?
C18 C19 1.506(5) . ?
C20 C21 1.495(4) . ?
C20 C25 1.505(5) . ?
C21 C22 1.338(5) . ?
C22 C23 1.474(7) . ?
C23 C24 1.437(6) . ?
C24 C25 1.328(5) . ?
C26 C28 1.496(5) . ?
C27 C28 1.366(6) . ?
C28 C29 1.453(6) . ?

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 O1 Si1 128.9(2) . . ?
C16 O2 C18 107.5(2) . . ?
C18 O3 C15 109.8(2) . . ?
O1 Si1 C2 110.07(17) . . ?
O1 Si1 C5 103.8(2) . . ?
O1 Si1 C8 110.05(16) . . ?
C2 Si1 C8 108.2(2) . . ?
C5 Si1 C2 113.1(4) . . ?
C5 Si1 C8 111.5(3) . . ?
C1 C2 Si1 113.6(4) . . ?
C3 C2 Si1 113.3(4) . . ?
C3 C2 C1 110.9(4) . . ?
C4 C5 Si1 118.6(5) . . ?
C6 C5 Si1 118.9(4) . . ?
C6 C5 C4 120.7(6) . . ?
C7 C8 Si1 113.4(3) . . ?
C7 C8 C9 109.7(5) . . ?
C9 C8 Si1 113.3(3) . . ?
O1 C11 C12 109.8(2) . . ?
C11 C12 C16 115.3(2) . . ?
C13 C12 C11 114.4(2) . . ?
C13 C12 C16 102.7(2) . . ?
C12 C13 C14 103.5(2) . . ?
C13 C14 C15 104.6(2) . . ?
C13 C14 C20 115.1(2) . . ?
C20 C14 C15 119.1(2) . . ?
O3 C15 C14 111.4(2) . . ?
O3 C15 C16 103.4(2) . . ?
O3 C15 C26 106.9(2) . . ?
C16 C15 C14 104.4(2) . . ?
C26 C15 C14 113.7(2) . . ?
C26 C15 C16 116.7(2) . . ?
O2 C16 C12 108.4(2) . . ?
O2 C16 C15 104.1(2) . . ?
C12 C16 C15 106.8(2) . . ?
O2 C18 C17 108.8(3) . . ?
O2 C18 C19 110.9(3) . . ?
O3 C18 O2 103.7(2) . . ?
O3 C18 C17 107.9(3) . . ?
O3 C18 C19 111.7(3) . . ?
C17 C18 C19 113.4(3) . . ?
O4 C20 C14 106.6(2) . . ?
O4 C20 C21 110.2(2) . . ?
O4 C20 C25 108.5(2) . . ?
C21 C20 C14 112.5(2) . . ?
C21 C20 C25 111.9(3) . . ?
C25 C20 C14 106.8(2) . . ?
C22 C21 C20 122.6(4) . . ?
C21 C22 C23 122.0(4) . . ?
O5 C23 C22 119.5(5) . . ?
O5 C23 C24 123.3(5) . . ?
C24 C23 C22 117.1(3) . . ?
C25 C24 C23 120.9(4) . . ?
C24 C25 C20 124.8(3) . . ?
C28 C26 C15 117.0(3) . . ?
C27 C28 C26 120.3(4) . . ?
C27 C28 C29 121.2(4) . . ?
C29 C28 C26 118.4(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1850229'
loop_
_audit_author_name
_audit_author_address
'Tong guanghu'
;Xi'an Jiaotong University
China
;
_audit_update_record             
;
2018-06-19 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31.50 H33 N4 O8'
_chemical_formula_weight         595.62

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pnna '

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

_cell_length_a                   17.706(9)
_cell_length_b                   13.192(7)
_cell_length_c                   26.864(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6275(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4343
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      19.36

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.149
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_max          0.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2512
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31145
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         24.78
_reflns_number_total             5374
_reflns_number_gt                2347
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1565P)²+2.2145P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5374
_refine_ls_number_parameters     376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1827
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.3179
_refine_ls_wR_factor_gt          0.2517
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7174(3) 0.1284(3) 0.6848(2) 0.0954(14) Uani 1 1 d . . .
N2 N 0.7945(3) 0.1313(3) 0.69203(18) 0.0954(13) Uani 1 1 d . . .
N3 N 0.5536(4) 0.1247(4) 0.6721(3) 0.1237(18) Uani 1 1 d . . .
N4 N 0.5270(9) 0.1078(5) 0.8505(4) 0.195(5) Uani 1 1 d . . .
O1 O 1.02053(16) 0.1497(2) 0.54007(12) 0.0847(10) Uani 1 1 d . . .
O2 O 1.13100(19) 0.2302(3) 0.52879(16) 0.1148(13) Uani 1 1 d . . .
O3 O 1.1831(3) 0.4646(5) 0.4697(3) 0.212(3) Uani 1 1 d . . .
O4 O 0.8590(2) 0.3631(3) 0.60003(17) 0.1198(14) Uani 1 1 d . . .
H4 H 0.8750 0.4167 0.5888 0.180 Uiso 1 1 calc R . .
O5 O 0.5919(3) 0.1329(4) 0.63416(19) 0.1396(16) Uani 1 1 d . . .
O6 O 0.4859(4) 0.1212(5) 0.6701(2) 0.198(3) Uani 1 1 d . . .
O7 O 0.4579(6) 0.1064(7) 0.8422(4) 0.247(6) Uani 1 1 d . . .
O8 O 0.5545(7) 0.1054(5) 0.8903(3) 0.251(6) Uani 1 1 d . . .
C1 C 0.5447(5) 0.1155(4) 0.7613(3) 0.133(3) Uani 1 1 d . . .
H1 H 0.4924 0.1160 0.7580 0.159 Uiso 1 1 calc R . .
C2 C 0.5768(8) 0.1110(5) 0.8068(4) 0.147(4) Uani 1 1 d . . .
C3 C 0.6540(8) 0.1107(5) 0.8135(3) 0.147(3) Uani 1 1 d . . .
H3A H 0.6741 0.1064 0.8454 0.176 Uiso 1 1 calc R . .
C4 C 0.7009(5) 0.1167(4) 0.7731(3) 0.118(2) Uani 1 1 d . . .
H4A H 0.7530 0.1176 0.7776 0.142 Uiso 1 1 calc R . .
C5 C 0.6701(4) 0.1217(3) 0.7243(2) 0.0961(17) Uani 1 1 d . . .
C6 C 0.5907(5) 0.1195(3) 0.7194(3) 0.1014(19) Uani 1 1 d . . .
C7 C 0.8333(3) 0.1468(3) 0.6523(2) 0.0885(15) Uani 1 1 d . . .
C8 C 0.9164(3) 0.1491(4) 0.6569(2) 0.1031(17) Uani 1 1 d . . .
H8A H 0.9376 0.0916 0.6393 0.124 Uiso 1 1 calc R . .
H8B H 0.9302 0.1428 0.6917 0.124 Uiso 1 1 calc R . .
C9 C 0.9503(3) 0.2470(4) 0.6359(2) 0.0963(16) Uani 1 1 d . . .
H9 H 1.0028 0.2319 0.6272 0.116 Uiso 1 1 calc R . .
C10 C 0.9105(3) 0.2816(3) 0.5872(2) 0.0871(15) Uani 1 1 d . . .
C11 C 0.8637(2) 0.1956(4) 0.5649(2) 0.0821(14) Uani 1 1 d . . .
H11 H 0.8975 0.1372 0.5616 0.099 Uiso 1 1 calc R . .
C12 C 0.8011(3) 0.1646(4) 0.6018(2) 0.0911(15) Uani 1 1 d . . .
H12A H 0.7633 0.2177 0.6035 0.109 Uiso 1 1 calc R . .
H12B H 0.7766 0.1032 0.5901 0.109 Uiso 1 1 calc R . .
C13 C 0.9525(4) 0.3287(5) 0.6766(2) 0.136(2) Uani 1 1 d . . .
H13A H 0.9734 0.3900 0.6631 0.204 Uiso 1 1 calc R . .
H13B H 0.9833 0.3058 0.7037 0.204 Uiso 1 1 calc R . .
H13C H 0.9022 0.3415 0.6883 0.204 Uiso 1 1 calc R . .
C14 C 0.9658(3) 0.3221(4) 0.5471(2) 0.0915(15) Uani 1 1 d . . .
H14 H 0.9351 0.3645 0.5250 0.110 Uiso 1 1 calc R . .
C15 C 1.0326(3) 0.3893(4) 0.5631(2) 0.118(2) Uani 1 1 d . . .
H15A H 1.0157 0.4560 0.5735 0.142 Uiso 1 1 calc R . .
H15B H 1.0612 0.3583 0.5899 0.142 Uiso 1 1 calc R . .
C16 C 1.0785(3) 0.3946(4) 0.5153(2) 0.115(2) Uani 1 1 d . . .
H16 H 1.0485 0.4326 0.4910 0.138 Uiso 1 1 calc R . .
C17 C 1.0798(3) 0.2851(4) 0.4986(3) 0.0997(17) Uani 1 1 d . . .
H17 H 1.0908 0.2781 0.4630 0.120 Uiso 1 1 calc R . .
C18 C 1.0021(2) 0.2400(4) 0.51283(19) 0.0814(14) Uani 1 1 d . . .
C19 C 0.9538(2) 0.2189(4) 0.46752(19) 0.0931(16) Uani 1 1 d . . .
H19A H 0.9681 0.2674 0.4420 0.112 Uiso 1 1 calc R . .
H19B H 0.9676 0.1523 0.4552 0.112 Uiso 1 1 calc R . .
C20 C 0.8689(3) 0.2217(4) 0.4720(2) 0.0910(15) Uani 1 1 d . . .
C21 C 0.8313(3) 0.2151(4) 0.5147(2) 0.0922(16) Uani 1 1 d . . .
H21 H 0.7792 0.2235 0.5130 0.111 Uiso 1 1 calc R . .
C22 C 1.1548(4) 0.4463(6) 0.5193(3) 0.158(3) Uani 1 1 d . . .
H22A H 1.1498 0.5100 0.5370 0.189 Uiso 1 1 calc R . .
H22B H 1.1898 0.4035 0.5375 0.189 Uiso 1 1 calc R . .
C23 C 1.1160(3) 0.0633(4) 0.4918(2) 0.117(2) Uani 1 1 d . . .
H23A H 1.1000 0.0966 0.4618 0.176 Uiso 1 1 calc R . .
H23B H 1.0891 0.0006 0.4954 0.176 Uiso 1 1 calc R . .
H23C H 1.1692 0.0500 0.4901 0.176 Uiso 1 1 calc R . .
C24 C 1.0996(3) 0.1309(4) 0.5359(3) 0.1017(18) Uani 1 1 d . . .
C25 C 1.1266(3) 0.0884(5) 0.5853(3) 0.133(2) Uani 1 1 d . . .
H25A H 1.1785 0.0679 0.5823 0.199 Uiso 1 1 calc R . .
H25B H 1.0963 0.0309 0.5942 0.199 Uiso 1 1 calc R . .
H25C H 1.1223 0.1395 0.6106 0.199 Uiso 1 1 calc R . .
C26 C 0.8299(3) 0.2374(6) 0.4230(2) 0.125(2) Uani 1 1 d . . .
H26A H 0.7763 0.2406 0.4281 0.188 Uiso 1 1 calc R . .
H26B H 0.8415 0.1820 0.4011 0.188 Uiso 1 1 calc R . .
H26C H 0.8471 0.2997 0.4083 0.188 Uiso 1 1 calc R . .
C29 C 0.189(2) 0.116(4) 0.8228(14) 0.517(18) Uiso 1 1 d . . .
C30 C 0.1305(16) 0.409(2) 0.7646(9) 0.435(13) Uiso 1 1 d . . .
C28 C 0.210(4) -0.018(9) 0.8180(19) 0.87(5) Uiso 1 1 d . . .
C32 C 0.322(3) 0.2500 0.7500 0.58(3) Uiso 1 2 d S . .
C27 C 0.277(3) 0.396(3) 0.7824(16) 0.62(2) Uiso 1 1 d . . .
C33 C 0.1898(19) 0.234(3) 0.7966(12) 0.504(18) Uiso 1 1 d . . .
H1N H 0.698(4) 0.134(6) 0.653(3) 0.18(4) Uiso 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
N1 C5 1.354(7) . ?
N1 N2 1.381(6) . ?
N2 C7 1.286(6) . ?
N3 O6 1.201(7) . ?
N3 O5 1.230(6) . ?
N3 C6 1.432(8) . ?
N4 O8 1.173(15) . ?
N4 O7 1.244(15) . ?
N4 C2 1.470(12) . ?
O1 C24 1.426(6) . ?
O1 C18 1.436(6) . ?
O2 C17 1.416(7) . ?
O2 C24 1.436(6) . ?
O3 C22 1.444(8) . ?
O4 C10 1.451(5) . ?
C1 C2 1.349(12) . ?
C1 C6 1.390(9) . ?
C2 C3 1.379(12) . ?
C3 C4 1.369(10) . ?
C4 C5 1.423(9) . ?
C5 C6 1.412(9) . ?
C7 C8 1.478(7) . ?
C7 C12 1.489(7) . ?
C8 C9 1.531(7) . ?
C9 C13 1.536(7) . ?
C9 C10 1.555(7) . ?
C10 C11 1.528(7) . ?
C10 C14 1.549(7) . ?
C11 C21 1.487(7) . ?
C11 C12 1.542(6) . ?
C14 C15 1.540(7) . ?
C14 C18 1.561(6) . ?
C15 C16 1.521(7) . ?
C16 C17 1.513(8) . ?
C16 C22 1.518(8) . ?
C17 C18 1.547(6) . ?
C18 C19 1.513(6) . ?
C19 C20 1.509(6) . ?
C20 C21 1.329(6) . ?
C20 C26 1.502(7) . ?
C23 C24 1.512(8) . ?
C24 C25 1.517(8) . ?
C29 C33 1.71(4) . ?
C29 C28 1.82(11) . ?
C28 C28 1.50(13) 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
C5 N1 N2 120.2(7) . . ?
C7 N2 N1 114.5(5) . . ?
O6 N3 O5 121.0(8) . . ?
O6 N3 C6 119.8(7) . . ?
O5 N3 C6 119.2(6) . . ?
O8 N4 O7 124.8(12) . . ?
O8 N4 C2 118.6(16) . . ?
O7 N4 C2 116.6(14) . . ?
C24 O1 C18 109.1(4) . . ?
C17 O2 C24 107.2(4) . . ?
C2 C1 C6 119.2(8) . . ?
C1 C2 C3 122.5(7) . . ?
C1 C2 N4 118.2(13) . . ?
C3 C2 N4 119.3(13) . . ?
C4 C3 C2 119.9(9) . . ?
C3 C4 C5 120.1(8) . . ?
N1 C5 C6 123.0(7) . . ?
N1 C5 C4 119.3(7) . . ?
C6 C5 C4 117.7(6) . . ?
C1 C6 C5 120.7(8) . . ?
C1 C6 N3 116.8(8) . . ?
C5 C6 N3 122.5(6) . . ?
N2 C7 C8 117.7(6) . . ?
N2 C7 C12 125.2(5) . . ?
C8 C7 C12 117.0(5) . . ?
C7 C8 C9 112.1(5) . . ?
C8 C9 C13 109.9(5) . . ?
C8 C9 C10 112.4(4) . . ?
C13 C9 C10 113.8(5) . . ?
O4 C10 C11 107.6(4) . . ?
O4 C10 C14 107.9(4) . . ?
C11 C10 C14 109.1(4) . . ?
O4 C10 C9 107.6(4) . . ?
C11 C10 C9 110.9(4) . . ?
C14 C10 C9 113.6(4) . . ?
C21 C11 C10 115.9(4) . . ?
C21 C11 C12 110.6(4) . . ?
C10 C11 C12 109.6(4) . . ?
C7 C12 C11 110.6(4) . . ?
C15 C14 C10 119.4(5) . . ?
C15 C14 C18 104.4(4) . . ?
C10 C14 C18 115.5(4) . . ?
C16 C15 C14 101.6(4) . . ?
C17 C16 C22 115.8(5) . . ?
C17 C16 C15 102.4(4) . . ?
C22 C16 C15 115.9(6) . . ?
O2 C17 C16 109.2(5) . . ?
O2 C17 C18 103.4(4) . . ?
C16 C17 C18 106.2(4) . . ?
O1 C18 C19 112.7(4) . . ?
O1 C18 C17 104.0(4) . . ?
C19 C18 C17 112.0(4) . . ?
O1 C18 C14 111.7(4) . . ?
C19 C18 C14 111.7(4) . . ?
C17 C18 C14 104.2(4) . . ?
C20 C19 C18 119.6(4) . . ?
C21 C20 C26 122.4(4) . . ?
C21 C20 C19 124.5(5) . . ?
C26 C20 C19 113.0(5) . . ?
C20 C21 C11 126.9(4) . . ?
O3 C22 C16 108.6(6) . . ?
O1 C24 O2 103.4(4) . . ?
O1 C24 C23 110.6(4) . . ?
O2 C24 C23 111.0(5) . . ?
O1 C24 C25 107.8(5) . . ?
O2 C24 C25 109.4(5) . . ?
C23 C24 C25 114.0(5) . . ?
C33 C29 C28 149(4) . . ?
C28 C28 C29 83(9) 2 . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.78
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.053
