# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_TBAHBNADH2BNAD
_database_code_depnum_ccdc_archive 'CCDC 1452013'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, C8 H8 N2 O2, C8 H7 N2 O2'
_chemical_formula_sum            'C32 H51 N5 O4'
_chemical_formula_weight         569.78

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3025(3)
_cell_length_b                   13.6899(6)
_cell_length_c                   15.9951(7)
_cell_angle_alpha                90.908(3)
_cell_angle_beta                 99.985(3)
_cell_angle_gamma                104.369(3)
_cell_volume                     1731.16(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2103
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      19.56

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   multi-Scan

_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            19758
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.25
_reflns_number_total             6068
_reflns_number_gt                2993
_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)+(0.0000P)²+2.0000P] 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         6068
_refine_ls_number_parameters     377
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1527
_refine_ls_R_factor_gt           0.0839
_refine_ls_wR_factor_ref         0.2225
_refine_ls_wR_factor_gt          0.1765
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.137
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7 C 0.6982(5) 0.6863(3) 0.4232(3) 0.0670(12) Uani 1 1 d . . .
H7 H 0.6791 0.6723 0.4779 0.080 Uiso 1 1 calc R . .
C2 C 0.6434(5) 0.6094(3) 0.3596(3) 0.0688(12) Uani 1 1 d . . .
C6 C 0.7808(5) 0.7836(4) 0.4077(3) 0.0695(12) Uani 1 1 d . . .
C1 C 0.5602(6) 0.5084(4) 0.3807(3) 0.0780(13) Uani 1 1 d . . .
H1 H 0.5575 0.4968 0.4376 0.094 Uiso 1 1 calc R . .
C8 C 0.8357(6) 0.8657(4) 0.4739(3) 0.0799(13) Uani 1 1 d . . .
H8 H 0.8960 0.9294 0.4624 0.096 Uiso 1 1 calc R . .
C3 C 0.6726(7) 0.6307(4) 0.2778(3) 0.0898(15) Uani 1 1 d . . .
H3 H 0.6363 0.5803 0.2341 0.108 Uiso 1 1 calc R . .
C5 C 0.8105(7) 0.8024(4) 0.3267(4) 0.0954(16) Uani 1 1 d . . .
H5 H 0.8683 0.8667 0.3152 0.114 Uiso 1 1 calc R . .
C4 C 0.7551(8) 0.7267(5) 0.2625(4) 0.1087(19) Uani 1 1 d . . .
H4 H 0.7742 0.7410 0.2079 0.130 Uiso 1 1 calc R . .
C11 C 0.1033(5) 0.8952(3) 0.1054(3) 0.0686(12) Uani 1 1 d . . .
H11 H 0.0567 0.9240 0.0580 0.082 Uiso 1 1 calc R . .
C9 C 0.2068(5) 1.0660(3) 0.1761(3) 0.0701(12) Uani 1 1 d . . .
H9 H 0.1887 1.0947 0.1241 0.084 Uiso 1 1 calc R . .
C10 C 0.1905(5) 0.9574(3) 0.1771(3) 0.0686(12) Uani 1 1 d . . .
C12 C 0.0837(6) 0.7914(4) 0.1027(3) 0.0752(13) Uani 1 1 d . . .
C16 C -0.0126(7) 0.7264(4) 0.0277(3) 0.0863(15) Uani 1 1 d . . .
H16 H -0.0272 0.6569 0.0287 0.104 Uiso 1 1 calc R . .
C15 C 0.2627(7) 0.9120(4) 0.2475(3) 0.0890(15) Uani 1 1 d . . .
H15 H 0.3221 0.9515 0.2963 0.107 Uiso 1 1 calc R . .
C13 C 0.1574(7) 0.7488(4) 0.1728(4) 0.0972(16) Uani 1 1 d . . .
H13 H 0.1473 0.6796 0.1716 0.117 Uiso 1 1 calc R . .
C14 C 0.2454(8) 0.8092(5) 0.2443(4) 0.1054(18) Uani 1 1 d . . .
H14 H 0.2939 0.7800 0.2910 0.126 Uiso 1 1 calc R . .
C25 C 0.8177(5) 0.1502(3) 0.2069(3) 0.0777(13) Uani 1 1 d . . .
H25A H 0.8782 0.1781 0.1624 0.093 Uiso 1 1 calc R . .
H25B H 0.8942 0.1231 0.2473 0.093 Uiso 1 1 calc R . .
C21 C 0.6560(6) 0.2844(4) 0.1910(3) 0.0824(14) Uani 1 1 d . . .
H21A H 0.5481 0.2352 0.1738 0.099 Uiso 1 1 calc R . .
H21B H 0.6355 0.3406 0.2215 0.099 Uiso 1 1 calc R . .
C17 C 0.9417(5) 0.3120(4) 0.2877(3) 0.0926(16) Uani 1 1 d . . .
H17A H 1.0119 0.2778 0.3251 0.111 Uiso 1 1 calc R . .
H17B H 0.9989 0.3339 0.2407 0.111 Uiso 1 1 calc R . .
C26 C 0.6694(6) 0.0639(4) 0.1674(3) 0.0904(15) Uani 1 1 d . . .
H26A H 0.5895 0.0899 0.1282 0.108 Uiso 1 1 calc R . .
H26B H 0.6120 0.0319 0.2116 0.108 Uiso 1 1 calc R . .
C27 C 0.7299(7) -0.0136(4) 0.1203(4) 0.1001(17) Uani 1 1 d . . .
H27A H 0.7865 0.0194 0.0762 0.120 Uiso 1 1 calc R . .
H27B H 0.8125 -0.0371 0.1598 0.120 Uiso 1 1 calc R . .
C22 C 0.7218(7) 0.3224(4) 0.1118(4) 0.1044(17) Uani 1 1 d . . .
H22A H 0.8338 0.3678 0.1276 0.125 Uiso 1 1 calc R . .
H22B H 0.7301 0.2660 0.0769 0.125 Uiso 1 1 calc R . .
C18 C 0.9276(7) 0.4040(5) 0.3358(5) 0.136(3) Uani 1 1 d . . .
H18A H 0.8891 0.3852 0.3886 0.163 Uiso 1 1 calc R . .
H18B H 0.8468 0.4349 0.3022 0.163 Uiso 1 1 calc R . .
C24 C 0.6494(12) 0.4117(6) -0.0198(5) 0.184(4) Uani 1 1 d . . .
H24A H 0.7574 0.4601 -0.0092 0.277 Uiso 1 1 calc R . .
H24B H 0.5656 0.4424 -0.0493 0.277 Uiso 1 1 calc R . .
H24C H 0.6553 0.3549 -0.0539 0.277 Uiso 1 1 calc R . .
C23 C 0.6027(10) 0.3775(6) 0.0620(4) 0.141(3) Uani 1 1 d . . .
H23A H 0.4895 0.3330 0.0509 0.169 Uiso 1 1 calc R . .
H23B H 0.6004 0.4357 0.0967 0.169 Uiso 1 1 calc R . .
C28 C 0.5934(8) -0.1029(5) 0.0803(4) 0.132(2) Uani 1 1 d . . .
H28A H 0.5480 -0.1423 0.1240 0.198 Uiso 1 1 calc R . .
H28B H 0.6391 -0.1436 0.0461 0.198 Uiso 1 1 calc R . .
H28C H 0.5051 -0.0804 0.0452 0.198 Uiso 1 1 calc R . .
C19 C 1.1014(8) 0.4780(7) 0.3544(7) 0.226(6) Uani 1 1 d D . .
H19A H 1.1781 0.4458 0.3897 0.271 Uiso 1 1 calc R . .
H19B H 1.1411 0.4902 0.3011 0.271 Uiso 1 1 calc R . .
C20 C 1.1129(13) 0.5718(9) 0.3948(9) 0.320(8) Uani 1 1 d D . .
H20A H 1.1525 0.6248 0.3590 0.480 Uiso 1 1 calc R . .
H20B H 1.1907 0.5805 0.4479 0.480 Uiso 1 1 calc R . .
H20C H 1.0035 0.5744 0.4051 0.480 Uiso 1 1 calc R . .
C29 C 0.6731(6) 0.1978(4) 0.3225(3) 0.0850(14) Uani 1 1 d . . .
H29A H 0.5647 0.1536 0.2964 0.102 Uiso 1 1 calc R . .
H29B H 0.6511 0.2551 0.3506 0.102 Uiso 1 1 calc R . .
C30 C 0.7611(8) 0.1405(5) 0.3899(4) 0.124(2) Uani 1 1 d . . .
H30A H 0.8699 0.1836 0.4168 0.149 Uiso 1 1 calc R . .
H30B H 0.7802 0.0813 0.3633 0.149 Uiso 1 1 calc R . .
C31 C 0.6484(9) 0.1082(7) 0.4579(4) 0.146(3) Uani 1 1 d . . .
H31A H 0.5328 0.0795 0.4290 0.175 Uiso 1 1 calc R . .
H31B H 0.6860 0.0556 0.4896 0.175 Uiso 1 1 calc R . .
C32 C 0.6505(10) 0.1871(8) 0.5153(5) 0.183(4) Uani 1 1 d . . .
H32A H 0.7653 0.2235 0.5369 0.275 Uiso 1 1 calc R . .
H32B H 0.5974 0.1598 0.5615 0.275 Uiso 1 1 calc R . .
H32C H 0.5901 0.2321 0.4867 0.275 Uiso 1 1 calc R . .
N4 N -0.0769(5) 0.7633(3) -0.0390(3) 0.0787(11) Uani 1 1 d . . .
N3 N 0.2453(4) 1.1233(3) 0.2449(2) 0.0732(10) Uani 1 1 d . . .
N2 N 0.4914(5) 0.4357(3) 0.3260(2) 0.0752(10) Uani 1 1 d . . .
N5 N 0.7729(4) 0.2359(3) 0.2523(2) 0.0765(11) Uani 1 1 d . . .
N1 N 0.7992(5) 0.8488(3) 0.5495(3) 0.0831(12) Uani 1 1 d . . .
O3 O 0.2598(4) 1.2238(2) 0.2355(2) 0.0831(9) Uani 1 1 d . . .
O2 O 0.4194(5) 0.3487(3) 0.3638(2) 0.0927(10) Uani 1 1 d . . .
H2 H 0.3779 0.3025 0.3272 0.139 Uiso 1 1 calc R . .
O1 O 0.8589(5) 0.9360(3) 0.6017(2) 0.1010(11) Uani 1 1 d . . .
H1A H 0.8548 0.9224 0.6511 0.151 Uiso 1 1 calc R . .
O4 O -0.1613(5) 0.6888(2) -0.1024(2) 0.1020(11) Uani 1 1 d . . .
H4A H -0.1991 0.7150 -0.1446 0.153 Uiso 1 1 calc R . .


_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
C7 C2 1.385(6) . ?
C7 C6 1.385(6) . ?
C2 C3 1.393(6) . ?
C2 C1 1.458(6) . ?
C6 C5 1.376(6) . ?
C6 C8 1.461(6) . ?
C1 N2 1.264(5) . ?
C8 N1 1.308(6) . ?
C3 C4 1.370(7) . ?
C5 C4 1.381(7) . ?
C11 C12 1.389(6) . ?
C11 C10 1.392(6) . ?
C9 N3 1.286(5) . ?
C9 C10 1.459(6) . ?
C10 C15 1.411(6) . ?
C12 C13 1.389(7) . ?
C12 C16 1.467(6) . ?
C16 N4 1.277(6) . ?
C15 C14 1.378(7) . ?
C13 C14 1.380(7) . ?
C25 C26 1.515(6) . ?
C25 N5 1.525(5) . ?
C21 C22 1.515(6) . ?
C21 N5 1.535(5) . ?
C17 C18 1.506(7) . ?
C17 N5 1.533(5) . ?
C26 C27 1.523(6) . ?
C27 C28 1.491(7) . ?
C22 C23 1.515(7) . ?
C18 C19 1.520(8) . ?
C24 C23 1.479(8) . ?
C19 C20 1.402(10) . ?
C29 N5 1.532(5) . ?
C29 C30 1.532(7) . ?
C30 C31 1.554(8) . ?
C31 C32 1.402(9) . ?
N4 O4 1.389(4) . ?
N3 O3 1.364(4) . ?
N2 O2 1.392(5) . ?
N1 O1 1.378(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C7 C6 121.8(4) . . ?
C7 C2 C3 118.9(5) . . ?
C7 C2 C1 119.0(4) . . ?
C3 C2 C1 122.1(4) . . ?
C5 C6 C7 118.2(4) . . ?
C5 C6 C8 119.5(5) . . ?
C7 C6 C8 122.2(4) . . ?
N2 C1 C2 123.7(5) . . ?
N1 C8 C6 119.3(5) . . ?
C4 C3 C2 119.3(5) . . ?
C6 C5 C4 120.5(5) . . ?
C3 C4 C5 121.2(5) . . ?
C12 C11 C10 122.0(4) . . ?
N3 C9 C10 122.1(4) . . ?
C11 C10 C15 117.8(4) . . ?
C11 C10 C9 119.5(4) . . ?
C15 C10 C9 122.7(4) . . ?
C11 C12 C13 118.9(4) . . ?
C11 C12 C16 121.4(5) . . ?
C13 C12 C16 119.7(5) . . ?
N4 C16 C12 121.4(5) . . ?
C14 C15 C10 120.2(5) . . ?
C14 C13 C12 120.1(5) . . ?
C15 C14 C13 121.0(5) . . ?
C26 C25 N5 115.6(4) . . ?
C22 C21 N5 115.3(4) . . ?
C18 C17 N5 115.1(4) . . ?
C25 C26 C27 110.4(4) . . ?
C28 C27 C26 114.6(5) . . ?
C23 C22 C21 109.5(5) . . ?
C17 C18 C19 108.1(5) . . ?
C24 C23 C22 113.8(6) . . ?
C20 C19 C18 116.9(7) . . ?
N5 C29 C30 114.8(4) . . ?
C29 C30 C31 109.4(5) . . ?
C32 C31 C30 114.1(7) . . ?
C16 N4 O4 111.9(4) . . ?
C9 N3 O3 116.5(4) . . ?
C1 N2 O2 111.4(4) . . ?
C25 N5 C29 111.8(4) . . ?
C25 N5 C17 105.8(3) . . ?
C29 N5 C17 112.0(4) . . ?
C25 N5 C21 111.1(3) . . ?
C29 N5 C21 104.9(3) . . ?
C17 N5 C21 111.4(4) . . ?
C8 N1 O1 110.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_2H2BNAD_TBAF
_database_code_depnum_ccdc_archive 'CCDC 1452014'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, 2(C8 H8 N2 O2), F'
_chemical_formula_sum            'C32 H52 F N5 O4'
_chemical_formula_weight         589.79

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.7631(8)
_cell_length_b                   8.2356(3)
_cell_length_c                   21.9337(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.378(2)
_cell_angle_gamma                90.00
_cell_volume                     3579.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3665
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      19.20

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   multi-Scan

_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            29694
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.25
_reflns_number_total             6383
_reflns_number_gt                3317
_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)+(0.0200P)²+3.0000P] 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         6383
_refine_ls_number_parameters     390
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1613
_refine_ls_wR_factor_gt          0.1388
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.228
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C15 C 0.96536(18) 0.8638(5) 0.39567(19) 0.0698(10) Uani 1 1 d . . .
H15 H 0.9715 0.9114 0.4355 0.084 Uiso 1 1 calc R . .
C10 C 1.01750(19) 0.8673(5) 0.3684(2) 0.0690(10) Uani 1 1 d . . .
C9 C 1.0821(2) 0.9376(5) 0.4040(2) 0.0745(11) Uani 1 1 d . . .
H9 H 1.0881 0.9776 0.4450 0.089 Uiso 1 1 calc R . .
C14 C 0.9041(2) 0.7905(5) 0.3646(2) 0.0736(11) Uani 1 1 d . . .
C2 C 0.4467(2) 0.0869(5) 0.6113(2) 0.0732(11) Uani 1 1 d . . .
C7 C 0.39271(19) 0.1535(5) 0.62768(19) 0.0748(11) Uani 1 1 d . . .
H7 H 0.3503 0.1560 0.5975 0.090 Uiso 1 1 calc R . .
C6 C 0.4006(2) 0.2164(5) 0.6883(2) 0.0749(11) Uani 1 1 d . . .
C16 C 0.8481(2) 0.7861(6) 0.3925(2) 0.0861(13) Uani 1 1 d . . .
H16 H 0.8104 0.7236 0.3727 0.103 Uiso 1 1 calc R . .
C8 C 0.3412(2) 0.2842(6) 0.7021(2) 0.0988(15) Uani 1 1 d . . .
H8 H 0.3015 0.2922 0.6684 0.119 Uiso 1 1 calc R . .
C13 C 0.8951(2) 0.7193(6) 0.3054(2) 0.0862(12) Uani 1 1 d . . .
H13 H 0.8545 0.6687 0.2845 0.103 Uiso 1 1 calc R . .
C11 C 1.0066(2) 0.7975(5) 0.3080(2) 0.0867(13) Uani 1 1 d . . .
H11 H 1.0406 0.8012 0.2883 0.104 Uiso 1 1 calc R . .
C1 C 0.4384(2) 0.0207(5) 0.5475(2) 0.0796(12) Uani 1 1 d . . .
H1 H 0.4732 -0.0397 0.5401 0.096 Uiso 1 1 calc R . .
C12 C 0.9461(3) 0.7234(6) 0.2774(2) 0.0950(14) Uani 1 1 d . . .
H12 H 0.9397 0.6758 0.2376 0.114 Uiso 1 1 calc R . .
C5 C 0.4638(2) 0.2130(6) 0.7329(2) 0.0909(13) Uani 1 1 d . . .
H5 H 0.4700 0.2551 0.7735 0.109 Uiso 1 1 calc R . .
C3 C 0.5089(2) 0.0846(6) 0.6571(2) 0.0962(15) Uani 1 1 d . . .
H3 H 0.5458 0.0401 0.6473 0.115 Uiso 1 1 calc R . .
C4 C 0.5171(2) 0.1472(7) 0.7169(2) 0.1093(17) Uani 1 1 d . . .
H4 H 0.5595 0.1450 0.7470 0.131 Uiso 1 1 calc R . .
C17 C 0.6794(2) -0.0784(5) 0.0958(2) 0.0960(14) Uani 1 1 d . . .
H17A H 0.6684 -0.1418 0.0568 0.115 Uiso 1 1 calc R . .
H17B H 0.6928 -0.1539 0.1314 0.115 Uiso 1 1 calc R . .
C21 C 0.7586(2) 0.1379(5) 0.1559(2) 0.0904(13) Uani 1 1 d . . .
H21A H 0.7216 0.2120 0.1533 0.108 Uiso 1 1 calc R . .
H21B H 0.7974 0.2024 0.1551 0.108 Uiso 1 1 calc R . .
C25 C 0.7972(2) -0.0840(5) 0.0983(2) 0.0926(14) Uani 1 1 d . . .
H25B H 0.8071 -0.1500 0.1366 0.111 Uiso 1 1 calc R . .
H25A H 0.7820 -0.1567 0.0620 0.111 Uiso 1 1 calc R . .
C29 C 0.7238(2) 0.1426(5) 0.0407(2) 0.0948(14) Uani 1 1 d . . .
H29B H 0.6873 0.2133 0.0430 0.114 Uiso 1 1 calc R . .
H29A H 0.7630 0.2107 0.0452 0.114 Uiso 1 1 calc R . .
C18 C 0.6157(2) 0.0087(6) 0.0988(3) 0.1046(15) Uani 1 1 d . . .
H18A H 0.6025 0.0886 0.0648 0.125 Uiso 1 1 calc R . .
H18B H 0.6244 0.0650 0.1393 0.125 Uiso 1 1 calc R . .
C30 C 0.7044(3) 0.0689(7) -0.0255(3) 0.130(2) Uani 1 1 d D . .
H30A H 0.6576 0.0344 -0.0379 0.156 Uiso 1 1 calc R . .
H30B H 0.7324 -0.0251 -0.0261 0.156 Uiso 1 1 calc R . .
C19 C 0.5591(2) -0.1145(6) 0.0916(3) 0.1092(16) Uani 1 1 d . . .
H19A H 0.5501 -0.1677 0.0504 0.131 Uiso 1 1 calc R . .
H19B H 0.5738 -0.1967 0.1245 0.131 Uiso 1 1 calc R . .
C27 C 0.9145(3) -0.1262(7) 0.0945(3) 0.1267(19) Uani 1 1 d . . .
H27A H 0.9314 -0.1725 0.1370 0.152 Uiso 1 1 calc R . .
H27B H 0.8925 -0.2133 0.0661 0.152 Uiso 1 1 calc R . .
C20 C 0.4959(3) -0.0391(7) 0.0965(3) 0.137(2) Uani 1 1 d . . .
H20A H 0.5044 0.0124 0.1374 0.205 Uiso 1 1 calc R . .
H20B H 0.4621 -0.1214 0.0920 0.205 Uiso 1 1 calc R . .
H20C H 0.4804 0.0404 0.0633 0.205 Uiso 1 1 calc R . .
C26 C 0.8617(3) -0.0055(6) 0.0959(3) 0.130(2) Uani 1 1 d . . .
H26A H 0.8525 0.0625 0.0582 0.156 Uiso 1 1 calc R . .
H26B H 0.8786 0.0638 0.1331 0.156 Uiso 1 1 calc R . .
C22 C 0.7752(3) 0.0473(7) 0.2194(3) 0.1279(19) Uani 1 1 d . . .
H22A H 0.7377 -0.0227 0.2194 0.154 Uiso 1 1 calc R . .
H22B H 0.8145 -0.0207 0.2238 0.154 Uiso 1 1 calc R . .
C23 C 0.7891(4) 0.1615(9) 0.2752(3) 0.156(2) Uani 1 1 d . . .
H23A H 0.7524 0.2391 0.2672 0.187 Uiso 1 1 calc R . .
H23B H 0.7891 0.0996 0.3128 0.187 Uiso 1 1 calc R . .
C28 C 0.9716(3) -0.0759(8) 0.0756(4) 0.174(3) Uani 1 1 d . . .
H28A H 0.9565 -0.0198 0.0355 0.262 Uiso 1 1 calc R . .
H28C H 0.9974 -0.1695 0.0711 0.262 Uiso 1 1 calc R . .
H28B H 0.9992 -0.0047 0.1074 0.262 Uiso 1 1 calc R . .
N3 N 1.13099(17) 0.9450(4) 0.37938(17) 0.0767(9) Uani 1 1 d . . .
N1 N 0.38479(18) 0.0440(4) 0.50210(17) 0.0772(9) Uani 1 1 d . . .
N2 N 0.33979(16) 0.3320(4) 0.75572(16) 0.0768(9) Uani 1 1 d . . .
N4 N 0.84916(16) 0.8637(4) 0.44238(18) 0.0784(9) Uani 1 1 d . . .
N5 N 0.73955(17) 0.0296(4) 0.09787(18) 0.0821(10) Uani 1 1 d . . .
O3 O 1.18839(14) 1.0132(4) 0.42141(14) 0.0871(9) Uani 1 1 d . . .
H3A H 1.2171 1.0267 0.4030 0.131 Uiso 1 1 calc R . .
O4 O 0.78939(14) 0.8405(4) 0.45857(15) 0.1002(10) Uani 1 1 d . . .
H4A H 0.7909 0.8940 0.4905 0.150 Uiso 1 1 calc R . .
O1 O 0.38803(18) -0.0329(4) 0.44642(17) 0.0939(9) Uani 1 1 d D . .
O2 O 0.27659(14) 0.3909(5) 0.75436(14) 0.1106(11) Uani 1 1 d . . .
H2 H 0.2765 0.4128 0.7908 0.166 Uiso 1 1 calc R . .
F1 F 0.27430(11) 0.0321(3) 0.36520(10) 0.0860(7) Uani 1 1 d . . .
C24 C 0.8515(4) 0.2497(9) 0.2889(4) 0.188(3) Uani 1 1 d . . .
H24B H 0.8867 0.1781 0.2856 0.281 Uiso 1 1 calc R . .
H24A H 0.8627 0.2928 0.3315 0.281 Uiso 1 1 calc R . .
H24C H 0.8467 0.3371 0.2590 0.281 Uiso 1 1 calc R . .
C31 C 0.7146(7) 0.1974(12) -0.0719(3) 0.297(8) Uani 1 1 d D . .
H31A H 0.7093 0.3036 -0.0549 0.356 Uiso 1 1 calc RD . .
H31B H 0.7607 0.1897 -0.0735 0.356 Uiso 1 1 calc R . .
C32 C 0.6737(6) 0.1883(19) -0.1308(6) 0.384(10) Uani 1 1 d D . .
H32A H 0.6794 0.2828 -0.1543 0.576 Uiso 1 1 calc R . .
H32B H 0.6278 0.1827 -0.1298 0.576 Uiso 1 1 calc R . .
H32C H 0.6841 0.0929 -0.1511 0.576 Uiso 1 1 calc R . .
H1A H 0.3502(16) -0.005(6) 0.4194(19) 0.12(2) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C15 C10 1.384(5) . ?
C15 C14 1.389(5) . ?
C10 C11 1.401(5) . ?
C10 C9 1.456(5) . ?
C9 N3 1.286(4) . ?
C14 C13 1.387(5) . ?
C14 C16 1.467(5) . ?
C2 C3 1.379(5) . ?
C2 C7 1.388(5) . ?
C2 C1 1.464(5) . ?
C7 C6 1.389(5) . ?
C6 C5 1.382(5) . ?
C6 C8 1.467(5) . ?
C16 N4 1.261(5) . ?
C8 N2 1.249(5) . ?
C13 C12 1.373(6) . ?
C11 C12 1.378(6) . ?
C1 N1 1.267(5) . ?
C5 C4 1.369(5) . ?
C3 C4 1.372(6) . ?
C17 C18 1.522(6) . ?
C17 N5 1.524(5) . ?
C21 N5 1.507(5) . ?
C21 C22 1.525(6) . ?
C25 C26 1.501(6) . ?
C25 N5 1.517(5) . ?
C29 C30 1.514(6) . ?
C29 N5 1.517(5) . ?
C18 C19 1.525(6) . ?
C30 C31 1.526(9) . ?
C19 C20 1.484(6) . ?
C27 C28 1.430(7) . ?
C27 C26 1.486(6) . ?
C22 C23 1.502(7) . ?
C23 C24 1.436(8) . ?
N3 O3 1.389(4) . ?
N1 O1 1.395(4) . ?
N2 O2 1.391(4) . ?
N4 O4 1.402(4) . ?
C31 C32 1.319(11) . ?

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
C10 C15 C14 121.1(4) . . ?
C15 C10 C11 118.3(4) . . ?
C15 C10 C9 119.4(4) . . ?
C11 C10 C9 122.2(4) . . ?
N3 C9 C10 120.6(4) . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 C16 118.6(4) . . ?
C15 C14 C16 122.0(4) . . ?
C3 C2 C7 118.1(4) . . ?
C3 C2 C1 120.5(4) . . ?
C7 C2 C1 121.4(4) . . ?
C2 C7 C6 121.3(4) . . ?
C5 C6 C7 119.1(4) . . ?
C5 C6 C8 122.7(4) . . ?
C7 C6 C8 118.2(4) . . ?
N4 C16 C14 122.6(4) . . ?
N2 C8 C6 124.9(4) . . ?
C12 C13 C14 120.2(4) . . ?
C12 C11 C10 120.6(4) . . ?
N1 C1 C2 121.3(4) . . ?
C13 C12 C11 120.4(4) . . ?
C4 C5 C6 119.7(4) . . ?
C4 C3 C2 120.8(4) . . ?
C5 C4 C3 121.0(4) . . ?
C18 C17 N5 116.0(4) . . ?
N5 C21 C22 114.3(4) . . ?
C26 C25 N5 116.4(4) . . ?
C30 C29 N5 118.5(4) . . ?
C17 C18 C19 109.5(4) . . ?
C29 C30 C31 108.2(5) . . ?
C20 C19 C18 112.7(4) . . ?
C28 C27 C26 119.5(5) . . ?
C27 C26 C25 112.6(4) . . ?
C23 C22 C21 112.0(5) . . ?
C24 C23 C22 115.4(6) . . ?
C9 N3 O3 111.6(3) . . ?
C1 N1 O1 111.0(4) . . ?
C8 N2 O2 112.1(3) . . ?
C16 N4 O4 111.3(3) . . ?
C21 N5 C29 105.8(3) . . ?
C21 N5 C25 110.6(3) . . ?
C29 N5 C25 111.0(3) . . ?
C21 N5 C17 112.1(3) . . ?
C29 N5 C17 111.2(3) . . ?
C25 N5 C17 106.2(3) . . ?
C32 C31 C30 115.9(11) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_2H2BNADTBAClH2O
_database_code_depnum_ccdc_archive 'CCDC 1452015'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, 2(C8 H8 N2 O2), Cl, H2 O'
_chemical_formula_sum            'C32 H54 Cl N5 O5'
_chemical_formula_weight         624.25

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.3315(9)
_cell_length_b                   8.5518(4)
_cell_length_c                   22.8978(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.077(3)
_cell_angle_gamma                90.00
_cell_volume                     3770.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2864
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      15.90

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.100
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   multi-Scan

_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            29993
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_sigmaI/netI    0.1072
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.06
_diffrn_reflns_theta_max         25.25
_reflns_number_total             6800
_reflns_number_gt                2100
_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)+(0.0400P)²+0.5000P] 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         6800
_refine_ls_number_parameters     404
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.2428
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.1632
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.26376(6) 0.02890(14) 0.04611(5) 0.1154(5) Uani 1 1 d . . .
C8 C 0.4503(3) 0.5214(6) 0.4179(3) 0.1139(18) Uani 1 1 d . . .
H8 H 0.4903 0.4829 0.4386 0.137 Uiso 1 1 calc R . .
C7 C 0.3996(2) 0.6394(6) 0.3238(3) 0.1039(15) Uani 1 1 d . . .
H7 H 0.3552 0.6140 0.3335 0.125 Uiso 1 1 calc R . .
C1 C 0.3438(3) 0.7551(7) 0.2353(2) 0.132(2) Uani 1 1 d . . .
H1 H 0.3013 0.7218 0.2469 0.159 Uiso 1 1 calc R . .
C2 C 0.4071(4) 0.7166(7) 0.2715(3) 0.1094(17) Uani 1 1 d . . .
C6 C 0.4571(4) 0.5988(6) 0.3622(3) 0.1045(16) Uani 1 1 d . . .
C5 C 0.5215(4) 0.6356(8) 0.3463(3) 0.148(2) Uani 1 1 d . . .
H5 H 0.5605 0.6075 0.3708 0.178 Uiso 1 1 calc R . .
C3 C 0.4728(5) 0.7545(7) 0.2575(2) 0.140(2) Uani 1 1 d . . .
H3 H 0.4788 0.8078 0.2228 0.168 Uiso 1 1 calc R . .
C4 C 0.5298(4) 0.7136(9) 0.2947(4) 0.175(3) Uani 1 1 d . . .
H4 H 0.5742 0.7388 0.2850 0.210 Uiso 1 1 calc R . .
C10 C 1.0323(3) 0.1704(5) 0.8687(2) 0.0882(13) Uani 1 1 d . . .
C9 C 1.0464(3) 0.1121(5) 0.9291(2) 0.0976(14) Uani 1 1 d . . .
H9 H 1.0092 0.0793 0.9492 0.117 Uiso 1 1 calc R . .
C14 C 0.9504(3) 0.2436(6) 0.7863(2) 0.0994(15) Uani 1 1 d . . .
C15 C 0.9643(3) 0.1810(5) 0.8426(2) 0.0961(14) Uani 1 1 d . . .
H15 H 0.9278 0.1460 0.8629 0.115 Uiso 1 1 calc R . .
C13 C 1.0048(4) 0.2944(7) 0.7567(2) 0.1299(19) Uani 1 1 d . . .
H13 H 0.9965 0.3377 0.7195 0.156 Uiso 1 1 calc R . .
C16 C 0.8784(3) 0.2509(7) 0.7624(2) 0.137(2) Uani 1 1 d . . .
H16 H 0.8433 0.2062 0.7821 0.164 Uiso 1 1 calc R . .
C11 C 1.0855(3) 0.2202(6) 0.8371(3) 0.1213(18) Uani 1 1 d . . .
H11 H 1.1312 0.2122 0.8534 0.146 Uiso 1 1 calc R . .
C12 C 1.0720(3) 0.2810(7) 0.7823(3) 0.147(2) Uani 1 1 d . . .
H12 H 1.1087 0.3142 0.7617 0.176 Uiso 1 1 calc R . .
C17 C 0.1883(3) 0.6365(6) 0.9727(2) 0.1332(18) Uani 1 1 d . . .
H17A H 0.1783 0.7030 1.0052 0.160 Uiso 1 1 calc R . .
H17B H 0.2057 0.7033 0.9430 0.160 Uiso 1 1 calc R . .
C25 C 0.2632(3) 0.4129(6) 0.9445(3) 0.1291(18) Uani 1 1 d . . .
H25A H 0.2996 0.3421 0.9599 0.155 Uiso 1 1 calc R . .
H25B H 0.2225 0.3504 0.9328 0.155 Uiso 1 1 calc R . .
C21 C 0.3081(3) 0.6240(6) 1.0155(2) 0.1373(19) Uani 1 1 d . . .
H21A H 0.3224 0.6831 0.9824 0.165 Uiso 1 1 calc R . .
H21B H 0.2935 0.6986 1.0438 0.165 Uiso 1 1 calc R . .
C29 C 0.2221(3) 0.4239(6) 1.0435(3) 0.1266(17) Uani 1 1 d . . .
H29A H 0.1840 0.3584 1.0276 0.152 Uiso 1 1 calc R . .
H29B H 0.2601 0.3553 1.0572 0.152 Uiso 1 1 calc R . .
C22 C 0.3707(3) 0.5355(7) 1.0433(3) 0.153(2) Uani 1 1 d . . .
H22A H 0.3853 0.4576 1.0161 0.184 Uiso 1 1 calc R . .
H22B H 0.3586 0.4822 1.0784 0.184 Uiso 1 1 calc R . .
C18 C 0.1209(3) 0.5638(6) 0.9473(3) 0.155(2) Uani 1 1 d . . .
H18A H 0.1290 0.5062 0.9121 0.186 Uiso 1 1 calc R . .
H18B H 0.1046 0.4905 0.9754 0.186 Uiso 1 1 calc R . .
C26 C 0.2864(4) 0.4914(8) 0.8913(3) 0.193(3) Uani 1 1 d . . .
H26A H 0.3306 0.5437 0.9002 0.232 Uiso 1 1 calc R . .
H26B H 0.2523 0.5674 0.8757 0.232 Uiso 1 1 calc R . .
C23 C 0.4299(3) 0.6507(7) 1.0590(3) 0.169(2) Uani 1 1 d . . .
H23A H 0.4437 0.6981 1.0233 0.203 Uiso 1 1 calc R . .
H23B H 0.4134 0.7333 1.0832 0.203 Uiso 1 1 calc R . .
C19 C 0.0665(3) 0.6849(7) 0.9329(3) 0.168(2) Uani 1 1 d . . .
H19A H 0.0588 0.7417 0.9684 0.202 Uiso 1 1 calc R . .
H19B H 0.0838 0.7589 0.9056 0.202 Uiso 1 1 calc R . .
C24 C 0.4900(4) 0.5772(9) 1.0900(3) 0.224(3) Uani 1 1 d . . .
H24A H 0.4783 0.5426 1.1278 0.335 Uiso 1 1 calc R . .
H24B H 0.5274 0.6511 1.0948 0.335 Uiso 1 1 calc R . .
H24C H 0.5040 0.4891 1.0679 0.335 Uiso 1 1 calc R . .
C20 C 0.0003(4) 0.6238(8) 0.9076(3) 0.210(3) Uani 1 1 d . . .
H20A H 0.0064 0.5765 0.8704 0.315 Uiso 1 1 calc R . .
H20B H -0.0327 0.7076 0.9023 0.315 Uiso 1 1 calc R . .
H20C H -0.0164 0.5468 0.9335 0.315 Uiso 1 1 calc R . .
C30 C 0.1991(3) 0.5108(7) 1.0952(3) 0.171(2) Uani 1 1 d . . .
H30B H 0.1560 0.5657 1.0839 0.205 Uiso 1 1 calc R . .
H30A H 0.2339 0.5875 1.1085 0.205 Uiso 1 1 calc R . .
N3 N 1.1071(2) 0.1049(4) 0.95496(18) 0.1019(12) Uani 1 1 d . . .
N1 N 0.3925(2) 0.5037(5) 0.4396(2) 0.1091(14) Uani 1 1 d . . .
N2 N 0.3450(2) 0.8330(5) 0.1882(2) 0.1274(14) Uani 1 1 d . . .
N5 N 0.2456(2) 0.5238(6) 0.9941(2) 0.1195(13) Uani 1 1 d . . .
N4 N 0.8646(2) 0.3225(5) 0.7122(2) 0.1297(15) Uani 1 1 d . . .
O3 O 1.10633(15) 0.0478(4) 1.01234(14) 0.1257(11) Uani 1 1 d . . .
H3A H 1.1462 0.0426 1.0277 0.189 Uiso 1 1 calc R . .
O1 O 0.40054(16) 0.4224(5) 0.49297(15) 0.1428(13) Uani 1 1 d . . .
H1A H 0.3657 0.4340 0.5105 0.214 Uiso 1 1 calc R . .
O4 O 0.7952(2) 0.3173(6) 0.69689(17) 0.1817(17) Uani 1 1 d . . .
H4A H 0.7851 0.3801 0.6704 0.273 Uiso 1 1 calc R . .
O2 O 0.2765(2) 0.8574(5) 0.16275(15) 0.1651(15) Uani 1 1 d . . .
H2 H 0.2778 0.8997 0.1307 0.248 Uiso 1 1 calc R . .
C27 C 0.2932(5) 0.3543(11) 0.8473(4) 0.265(5) Uani 1 1 d D . .
H27A H 0.3060 0.2601 0.8693 0.318 Uiso 1 1 calc R . .
H27B H 0.2482 0.3361 0.8261 0.318 Uiso 1 1 calc R . .
C31 C 0.1880(4) 0.3949(12) 1.1456(4) 0.229(4) Uani 1 1 d . . .
H31B H 0.1583 0.4433 1.1724 0.275 Uiso 1 1 calc R . .
H31A H 0.1645 0.3024 1.1294 0.275 Uiso 1 1 calc R . .
O5 O 0.7593(3) 0.4843(5) 0.59977(15) 0.1384(14) Uani 1 1 d D . .
C32 C 0.2496(5) 0.3513(11) 1.1762(4) 0.290(5) Uani 1 1 d . . .
H32B H 0.2793 0.3038 1.1499 0.435 Uiso 1 1 calc R . .
H32A H 0.2403 0.2778 1.2062 0.435 Uiso 1 1 calc R . .
H32C H 0.2720 0.4420 1.1939 0.435 Uiso 1 1 calc R . .
C28 C 0.3371(5) 0.3775(13) 0.8108(5) 0.358(7) Uani 1 1 d D . .
H28A H 0.3170 0.4427 0.7796 0.538 Uiso 1 1 calc R . .
H28B H 0.3505 0.2792 0.7950 0.538 Uiso 1 1 calc R . .
H28C H 0.3772 0.4282 0.8299 0.538 Uiso 1 1 calc R . .
H5A H 0.7141(13) 0.481(8) 0.589(3) 0.25(4) Uiso 1 1 d D . .
H5B H 0.794(3) 0.526(7) 0.581(2) 0.20(3) 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
C8 N1 1.273(5) . ?
C8 C6 1.451(6) . ?
C7 C2 1.386(6) . ?
C7 C6 1.400(6) . ?
C1 N2 1.269(5) . ?
C1 C2 1.455(6) . ?
C2 C3 1.376(6) . ?
C6 C5 1.364(6) . ?
C5 C4 1.379(7) . ?
C3 C4 1.377(6) . ?
C10 C11 1.376(5) . ?
C10 C15 1.398(5) . ?
C10 C9 1.474(5) . ?
C9 N3 1.269(4) . ?
C14 C13 1.371(6) . ?
C14 C15 1.400(5) . ?
C14 C16 1.450(6) . ?
C13 C12 1.381(6) . ?
C16 N4 1.309(5) . ?
C11 C12 1.364(6) . ?
C17 C18 1.513(6) . ?
C17 N5 1.517(5) . ?
C25 C26 1.493(6) . ?
C25 N5 1.541(6) . ?
C21 C22 1.519(6) . ?
C21 N5 1.526(5) . ?
C29 C30 1.500(6) . ?
C29 N5 1.517(5) . ?
C22 C23 1.528(6) . ?
C18 C19 1.492(6) . ?
C26 C27 1.560(9) . ?
C23 C24 1.450(7) . ?
C19 C20 1.454(6) . ?
C30 C31 1.550(9) . ?
N3 O3 1.403(4) . ?
N1 O1 1.402(4) . ?
N2 O2 1.415(4) . ?
N4 O4 1.357(4) . ?
C27 C28 1.259(6) . ?
C31 C32 1.378(8) . ?

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
N1 C8 C6 123.3(6) . . ?
C2 C7 C6 121.5(5) . . ?
N2 C1 C2 121.7(6) . . ?
C3 C2 C7 119.0(5) . . ?
C3 C2 C1 124.1(7) . . ?
C7 C2 C1 116.9(6) . . ?
C5 C6 C7 117.9(6) . . ?
C5 C6 C8 119.6(6) . . ?
C7 C6 C8 122.5(6) . . ?
C6 C5 C4 121.3(6) . . ?
C2 C3 C4 119.9(6) . . ?
C3 C4 C5 120.4(6) . . ?
C11 C10 C15 118.3(5) . . ?
C11 C10 C9 120.8(5) . . ?
C15 C10 C9 120.8(6) . . ?
N3 C9 C10 122.8(5) . . ?
C13 C14 C15 118.8(5) . . ?
C13 C14 C16 123.6(6) . . ?
C15 C14 C16 117.6(6) . . ?
C10 C15 C14 121.1(5) . . ?
C14 C13 C12 119.9(5) . . ?
N4 C16 C14 117.8(5) . . ?
C12 C11 C10 120.7(5) . . ?
C11 C12 C13 121.2(5) . . ?
C18 C17 N5 116.3(5) . . ?
C26 C25 N5 115.2(5) . . ?
C22 C21 N5 115.7(5) . . ?
C30 C29 N5 116.0(5) . . ?
C21 C22 C23 109.2(5) . . ?
C19 C18 C17 111.5(5) . . ?
C25 C26 C27 103.7(6) . . ?
C24 C23 C22 112.7(6) . . ?
C20 C19 C18 114.6(6) . . ?
C29 C30 C31 110.0(6) . . ?
C9 N3 O3 111.6(4) . . ?
C8 N1 O1 111.6(5) . . ?
C1 N2 O2 109.9(5) . . ?
C17 N5 C29 109.9(4) . . ?
C17 N5 C21 106.4(5) . . ?
C29 N5 C21 111.0(4) . . ?
C17 N5 C25 110.8(4) . . ?
C29 N5 C25 107.6(5) . . ?
C21 N5 C25 111.2(4) . . ?
C16 N4 O4 109.4(5) . . ?
C28 C27 C26 114.3(10) . . ?
C32 C31 C30 112.4(9) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.029
