# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1,6-bis(pyrazol-3-yl)hexane-hydrate
_database_code_depnum_ccdc_archive 'CCDC 1040198'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        1,6-bis(pyrazol-3(5)-yl)hexane
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H20 N4 O'
_chemical_formula_weight         236.32

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8013(4)
_cell_length_b                   9.2025(4)
_cell_length_c                   10.1004(5)
_cell_angle_alpha                107.833(3)
_cell_angle_beta                 93.710(4)
_cell_angle_gamma                114.352(3)
_cell_volume                     692.06(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4164
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      24.04

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6733
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13883
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.604
_diffrn_reflns_theta_max         24.119
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.876
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.876
_reflns_number_total             2194
_reflns_number_gt                1433
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2194
_refine_ls_number_parameters     160
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1577
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.956
_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 0.0154(2) 0.7476(2) 0.48294(17) 0.0585(5) Uani 1 1 d D . . . .
H1O H 0.084(3) 0.827(3) 0.456(2) 0.070 Uiso 1 1 d D U . . .
H2O H -0.011(3) 0.656(3) 0.415(2) 0.070 Uiso 1 1 d D U . . .
N1 N 0.0860(3) -0.4385(2) 0.7495(2) 0.0610(6) Uani 1 1 d . . . . .
N2 N 0.1011(2) -0.2897(2) 0.74103(19) 0.0530(5) Uani 1 1 d . . . . .
H2N H 0.0870 -0.2748 0.6620 0.064 Uiso 1 1 calc R U . . .
N3 N 0.7708(2) 0.8446(2) 0.59795(19) 0.0533(5) Uani 1 1 d . . . . .
H3N H 0.8466 0.8148 0.5678 0.064 Uiso 1 1 calc R U . . .
N4 N 0.7567(3) 0.9808(2) 0.5864(2) 0.0587(6) Uani 1 1 d . . . . .
C1 C 0.1181(4) -0.4075(4) 0.8871(3) 0.0774(9) Uani 1 1 d . . . . .
H1 H 0.1175 -0.4872 0.9259 0.093 Uiso 1 1 calc R U . . .
C2 C 0.1524(4) -0.2425(3) 0.9658(3) 0.0750(8) Uani 1 1 d . . . . .
H2 H 0.1785 -0.1911 1.0647 0.090 Uiso 1 1 calc R U . . .
C3 C 0.1403(3) -0.1685(3) 0.8690(2) 0.0506(6) Uani 1 1 d . . . . .
C4 C 0.1665(3) 0.0069(3) 0.8846(2) 0.0573(7) Uani 1 1 d . . . . .
H4B H 0.1838 0.0726 0.9847 0.069 Uiso 1 1 calc R U . . .
H4A H 0.0638 -0.0016 0.8342 0.069 Uiso 1 1 calc R U . . .
C5 C 0.3181(3) 0.1027(3) 0.8282(3) 0.0553(6) Uani 1 1 d . . . . .
H5B H 0.4223 0.1258 0.8880 0.066 Uiso 1 1 calc R U . . .
H5A H 0.3095 0.0289 0.7329 0.066 Uiso 1 1 calc R U . . .
C6 C 0.3327(3) 0.2700(3) 0.8224(2) 0.0547(6) Uani 1 1 d . . . . .
H6A H 0.3417 0.3445 0.9175 0.066 Uiso 1 1 calc R U . . .
H6B H 0.2292 0.2476 0.7620 0.066 Uiso 1 1 calc R U . . .
C7 C 0.4852(3) 0.3617(3) 0.7662(2) 0.0539(6) Uani 1 1 d . . . . .
H7B H 0.5888 0.3926 0.8315 0.065 Uiso 1 1 calc R U . . .
H7A H 0.4814 0.2829 0.6751 0.065 Uiso 1 1 calc R U . . .
C8 C 0.4949(3) 0.5216(3) 0.7468(2) 0.0516(6) Uani 1 1 d . . . . .
H8A H 0.3905 0.4919 0.6831 0.062 Uiso 1 1 calc R U . . .
H8B H 0.5024 0.6024 0.8382 0.062 Uiso 1 1 calc R U . . .
C9 C 0.6459(3) 0.6068(3) 0.6869(3) 0.0579(6) Uani 1 1 d . . . . .
H9B H 0.7502 0.6403 0.7526 0.070 Uiso 1 1 calc R U . . .
H9A H 0.6408 0.5241 0.5976 0.070 Uiso 1 1 calc R U . . .
C10 C 0.6543(3) 0.7607(3) 0.6613(2) 0.0498(6) Uani 1 1 d . . . . .
C11 C 0.5593(3) 0.8474(3) 0.6925(3) 0.0665(7) Uani 1 1 d . . . . .
H11 H 0.4674 0.8213 0.7369 0.080 Uiso 1 1 calc R U . . .
C12 C 0.6271(4) 0.9813(3) 0.6449(3) 0.0663(7) Uani 1 1 d . . . . .
H12 H 0.5867 1.0618 0.6529 0.080 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 H1O 0.867(17) . ?
O1 H2O 0.839(16) . ?
N1 C1 1.317(3) . ?
N1 N2 1.350(2) . ?
N2 C3 1.332(3) . ?
N2 H2N 0.8600 . ?
N3 C10 1.338(3) . ?
N3 N4 1.347(2) . ?
N3 H3N 0.8600 . ?
N4 C12 1.319(3) . ?
C1 C2 1.371(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.488(3) . ?
C4 C5 1.523(3) . ?
C4 H4B 0.9700 . ?
C4 H4A 0.9700 . ?
C5 C6 1.510(3) . ?
C5 H5B 0.9700 . ?
C5 H5A 0.9700 . ?
C6 C7 1.514(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.512(3) . ?
C7 H7B 0.9700 . ?
C7 H7A 0.9700 . ?
C8 C9 1.511(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.489(3) . ?
C9 H9B 0.9700 . ?
C9 H9A 0.9700 . ?
C10 C11 1.366(3) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1O O1 H2O 104(2) . . ?
C1 N1 N2 104.72(19) . . ?
C3 N2 N1 112.37(18) . . ?
C3 N2 H2N 123.8 . . ?
N1 N2 H2N 123.8 . . ?
C10 N3 N4 112.91(19) . . ?
C10 N3 H3N 123.5 . . ?
N4 N3 H3N 123.5 . . ?
C12 N4 N3 104.23(19) . . ?
N1 C1 C2 111.2(2) . . ?
N1 C1 H1 124.4 . . ?
C2 C1 H1 124.4 . . ?
C1 C2 C3 106.0(2) . . ?
C1 C2 H2 127.0 . . ?
C3 C2 H2 127.0 . . ?
N2 C3 C2 105.7(2) . . ?
N2 C3 C4 121.4(2) . . ?
C2 C3 C4 132.9(2) . . ?
C3 C4 C5 113.51(19) . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
H4B C4 H4A 107.7 . . ?
C6 C5 C4 114.74(19) . . ?
C6 C5 H5B 108.6 . . ?
C4 C5 H5B 108.6 . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5A 108.6 . . ?
H5B C5 H5A 107.6 . . ?
C5 C6 C7 113.17(19) . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 114.53(19) . . ?
C8 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
H7B C7 H7A 107.6 . . ?
C9 C8 C7 112.97(18) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 113.98(19) . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
H9B C9 H9A 107.7 . . ?
N3 C10 C11 105.5(2) . . ?
N3 C10 C9 122.5(2) . . ?
C11 C10 C9 132.0(2) . . ?
C10 C11 C12 106.1(2) . . ?
C10 C11 H11 127.0 . . ?
C12 C11 H11 127.0 . . ?
N4 C12 C11 111.3(2) . . ?
N4 C12 H12 124.3 . . ?
C11 C12 H12 124.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 -0.4(3) . . . . ?
C10 N3 N4 C12 0.1(3) . . . . ?
N2 N1 C1 C2 0.3(3) . . . . ?
N1 C1 C2 C3 0.0(3) . . . . ?
N1 N2 C3 C2 0.4(3) . . . . ?
N1 N2 C3 C4 178.74(19) . . . . ?
C1 C2 C3 N2 -0.2(3) . . . . ?
C1 C2 C3 C4 -178.3(3) . . . . ?
N2 C3 C4 C5 -63.6(3) . . . . ?
C2 C3 C4 C5 114.2(3) . . . . ?
C3 C4 C5 C6 171.40(19) . . . . ?
C4 C5 C6 C7 179.82(19) . . . . ?
C5 C6 C7 C8 174.85(18) . . . . ?
C6 C7 C8 C9 -178.49(19) . . . . ?
C7 C8 C9 C10 177.67(19) . . . . ?
N4 N3 C10 C11 0.0(3) . . . . ?
N4 N3 C10 C9 -179.49(19) . . . . ?
C8 C9 C10 N3 -174.4(2) . . . . ?
C8 C9 C10 C11 6.2(4) . . . . ?
N3 C10 C11 C12 -0.2(3) . . . . ?
C9 C10 C11 C12 179.3(2) . . . . ?
N3 N4 C12 C11 -0.2(3) . . . . ?
C10 C11 C12 N4 0.2(3) . . . . ?

_refine_diff_density_max         0.128
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-2



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water, methanol'
####################################################################### 
# 
# 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_5-n-hexadecyl-1-(tetrahydropyran-2-yl)pyrazole
_database_code_depnum_ccdc_archive 'CCDC 1040199'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
5-n-hexadecyl-1-(tetrahydropyran-2-yl)pyrazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H44 N2 O'
_chemical_formula_weight         376.61

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7407(5)
_cell_length_b                   9.4611(5)
_cell_length_c                   29.7000(15)
_cell_angle_alpha                92.436(3)
_cell_angle_beta                 91.591(3)
_cell_angle_gamma                104.178(3)
_cell_volume                     2377.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.54

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.063
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7212
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60311
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.223
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.938
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.938
_reflns_number_total             8085
_reflns_number_gt                5456
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0500P)²+0.3880P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8085
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.10260(14) 0.58570(12) 0.87109(4) 0.0729(3) Uani 1 1 d . . . . .
O2 O -0.37646(12) 0.83720(12) 0.89343(3) 0.0654(3) Uani 1 1 d . . . . .
N1 N 0.22968(14) 0.82675(13) 0.87873(4) 0.0546(3) Uani 1 1 d . . . . .
N2 N 0.17269(18) 0.92251(16) 0.90463(5) 0.0776(4) Uani 1 1 d . . . . .
N3 N -0.30771(15) 0.62063(14) 0.89936(4) 0.0611(3) Uani 1 1 d . . . . .
N4 N -0.38541(18) 0.51919(18) 0.92716(5) 0.0802(4) Uani 1 1 d . . . . .
C1 C 0.1872(3) 1.0361(2) 0.87981(7) 0.0911(6) Uani 1 1 d . . . . .
H1 H 0.1584 1.1208 0.8890 0.109 Uiso 1 1 calc R U . . .
C2 C 0.2503(2) 1.01616(18) 0.83833(6) 0.0759(5) Uani 1 1 d . . . . .
H2 H 0.2705 1.0818 0.8155 0.091 Uiso 1 1 calc R U . . .
C3 C 0.27616(17) 0.87996(16) 0.83823(5) 0.0535(4) Uani 1 1 d . . . . .
C4 C 0.34121(19) 0.79619(16) 0.80309(4) 0.0567(4) Uani 1 1 d . . . . .
H4A H 0.2650 0.7043 0.7956 0.068 Uiso 1 1 calc R U . . .
H4B H 0.4365 0.7743 0.8152 0.068 Uiso 1 1 calc R U . . .
C5 C 0.37915(18) 0.87881(16) 0.76048(5) 0.0545(4) Uani 1 1 d . . . . .
H5A H 0.2838 0.9017 0.7488 0.065 Uiso 1 1 calc R U . . .
H5B H 0.4556 0.9704 0.7682 0.065 Uiso 1 1 calc R U . . .
C6 C 0.44409(18) 0.79685(16) 0.72379(4) 0.0533(4) Uani 1 1 d . . . . .
H6A H 0.3669 0.7062 0.7156 0.064 Uiso 1 1 calc R U . . .
H6B H 0.5385 0.7724 0.7356 0.064 Uiso 1 1 calc R U . . .
C7 C 0.48422(17) 0.88236(15) 0.68179(4) 0.0526(4) Uani 1 1 d . . . . .
H7A H 0.3894 0.9057 0.6699 0.063 Uiso 1 1 calc R U . . .
H7B H 0.5601 0.9737 0.6902 0.063 Uiso 1 1 calc R U . . .
C8 C 0.55154(17) 0.80309(15) 0.64481(4) 0.0508(3) Uani 1 1 d . . . . .
H8A H 0.4749 0.7127 0.6359 0.061 Uiso 1 1 calc R U . . .
H8B H 0.6454 0.7781 0.6568 0.061 Uiso 1 1 calc R U . . .
C9 C 0.59420(17) 0.89055(15) 0.60327(4) 0.0506(3) Uani 1 1 d . . . . .
H9A H 0.5002 0.9150 0.5912 0.061 Uiso 1 1 calc R U . . .
H9B H 0.6703 0.9813 0.6122 0.061 Uiso 1 1 calc R U . . .
C10 C 0.66256(17) 0.81184(15) 0.56629(4) 0.0492(3) Uani 1 1 d . . . . .
H10A H 0.7560 0.7866 0.5784 0.059 Uiso 1 1 calc R U . . .
H10B H 0.5860 0.7215 0.5572 0.059 Uiso 1 1 calc R U . . .
C11 C 0.70649(17) 0.89946(15) 0.52498(4) 0.0497(3) Uani 1 1 d . . . . .
H11A H 0.7829 0.9899 0.5341 0.060 Uiso 1 1 calc R U . . .
H11B H 0.6130 0.9245 0.5128 0.060 Uiso 1 1 calc R U . . .
C12 C 0.77517(17) 0.82061(15) 0.48811(4) 0.0494(3) Uani 1 1 d . . . . .
H12A H 0.8684 0.7953 0.5004 0.059 Uiso 1 1 calc R U . . .
H12B H 0.6986 0.7303 0.4790 0.059 Uiso 1 1 calc R U . . .
C13 C 0.81986(17) 0.90794(15) 0.44671(4) 0.0503(3) Uani 1 1 d . . . . .
H13A H 0.8963 0.9983 0.4558 0.060 Uiso 1 1 calc R U . . .
H13B H 0.7266 0.9330 0.4343 0.060 Uiso 1 1 calc R U . . .
C14 C 0.88884(17) 0.82845(15) 0.41007(4) 0.0504(3) Uani 1 1 d . . . . .
H14A H 0.9820 0.8034 0.4225 0.060 Uiso 1 1 calc R U . . .
H14B H 0.8124 0.7380 0.4011 0.060 Uiso 1 1 calc R U . . .
C15 C 0.93375(17) 0.91487(15) 0.36852(5) 0.0517(3) Uani 1 1 d . . . . .
H15A H 1.0104 1.0053 0.3775 0.062 Uiso 1 1 calc R U . . .
H15B H 0.8407 0.9399 0.3560 0.062 Uiso 1 1 calc R U . . .
C16 C 1.00253(18) 0.83418(15) 0.33213(5) 0.0534(4) Uani 1 1 d . . . . .
H16A H 1.0961 0.8101 0.3447 0.064 Uiso 1 1 calc R U . . .
H16B H 0.9263 0.7432 0.3236 0.064 Uiso 1 1 calc R U . . .
C17 C 1.04642(18) 0.91775(16) 0.29015(5) 0.0558(4) Uani 1 1 d . . . . .
H17A H 1.1223 1.0091 0.2986 0.067 Uiso 1 1 calc R U . . .
H17B H 0.9528 0.9411 0.2774 0.067 Uiso 1 1 calc R U . . .
C18 C 1.1160(2) 0.83613(18) 0.25433(5) 0.0666(4) Uani 1 1 d . . . . .
H18A H 1.2094 0.8126 0.2672 0.080 Uiso 1 1 calc R U . . .
H18B H 1.0400 0.7448 0.2459 0.080 Uiso 1 1 calc R U . . .
C19 C 1.1602(2) 0.9182(2) 0.21251(6) 0.0867(6) Uani 1 1 d . . . . .
H19A H 1.0678 0.9389 0.1988 0.130 Uiso 1 1 calc R U . . .
H19B H 1.2042 0.8601 0.1917 0.130 Uiso 1 1 calc R U . . .
H19C H 1.2368 1.0081 0.2203 0.130 Uiso 1 1 calc R U . . .
C20 C 0.23006(18) 0.68477(16) 0.89452(4) 0.0552(4) Uani 1 1 d . . . . .
H20 H 0.3285 0.6608 0.8859 0.066 Uiso 1 1 calc R U . . .
C21 C 0.2178(2) 0.6763(2) 0.94467(5) 0.0768(5) Uani 1 1 d . . . . .
H21A H 0.1250 0.7070 0.9541 0.092 Uiso 1 1 calc R U . . .
H21B H 0.3100 0.7414 0.9597 0.092 Uiso 1 1 calc R U . . .
C22 C 0.2062(3) 0.5213(2) 0.95795(6) 0.0870(6) Uani 1 1 d . . . . .
H22A H 0.3052 0.4958 0.9525 0.104 Uiso 1 1 calc R U . . .
H22B H 0.1867 0.5141 0.9899 0.104 Uiso 1 1 calc R U . . .
C23 C 0.0745(3) 0.4170(2) 0.93109(7) 0.0934(6) Uani 1 1 d . . . . .
H23A H -0.0262 0.4341 0.9394 0.112 Uiso 1 1 calc R U . . .
H23B H 0.0745 0.3174 0.9376 0.112 Uiso 1 1 calc R U . . .
C24 C 0.0965(3) 0.43842(19) 0.88154(6) 0.0925(6) Uani 1 1 d . . . . .
H24A H 0.1937 0.4143 0.8730 0.111 Uiso 1 1 calc R U . . .
H24B H 0.0098 0.3730 0.8643 0.111 Uiso 1 1 calc R U . . .
C25 C -0.4130(2) 0.3964(2) 0.90239(7) 0.0841(5) Uani 1 1 d . . . . .
H25 H -0.4649 0.3062 0.9126 0.101 Uiso 1 1 calc R U . . .
C26 C -0.3559(2) 0.41643(19) 0.85934(6) 0.0740(5) Uani 1 1 d . . . . .
H26 H -0.3623 0.3453 0.8363 0.089 Uiso 1 1 calc R U . . .
C27 C -0.28874(18) 0.56183(17) 0.85796(5) 0.0574(4) Uani 1 1 d . . . . .
C28 C -0.21156(19) 0.65362(17) 0.82134(5) 0.0602(4) Uani 1 1 d . . . . .
H28A H -0.1187 0.7239 0.8341 0.072 Uiso 1 1 calc R U . . .
H28B H -0.2838 0.7077 0.8098 0.072 Uiso 1 1 calc R U . . .
C29 C -0.16286(18) 0.56718(16) 0.78246(5) 0.0553(4) Uani 1 1 d . . . . .
H29A H -0.0822 0.5211 0.7933 0.066 Uiso 1 1 calc R U . . .
H29B H -0.2533 0.4905 0.7716 0.066 Uiso 1 1 calc R U . . .
C30 C -0.09992(18) 0.66074(15) 0.74374(5) 0.0539(4) Uani 1 1 d . . . . .
H30A H -0.0141 0.7411 0.7552 0.065 Uiso 1 1 calc R U . . .
H30B H -0.1830 0.7019 0.7318 0.065 Uiso 1 1 calc R U . . .
C31 C -0.04080(17) 0.57888(15) 0.70568(4) 0.0525(4) Uani 1 1 d . . . . .
H31A H 0.0479 0.5445 0.7172 0.063 Uiso 1 1 calc R U . . .
H31B H -0.1240 0.4939 0.6960 0.063 Uiso 1 1 calc R U . . .
C32 C 0.01041(17) 0.66806(15) 0.66514(4) 0.0510(3) Uani 1 1 d . . . . .
H32A H 0.0916 0.7545 0.6750 0.061 Uiso 1 1 calc R U . . .
H32B H -0.0790 0.7001 0.6531 0.061 Uiso 1 1 calc R U . . .
C33 C 0.07362(17) 0.58659(15) 0.62775(4) 0.0515(3) Uani 1 1 d . . . . .
H33A H 0.1650 0.5572 0.6396 0.062 Uiso 1 1 calc R U . . .
H33B H -0.0064 0.4986 0.6186 0.062 Uiso 1 1 calc R U . . .
C34 C 0.12033(17) 0.67403(15) 0.58654(4) 0.0495(3) Uani 1 1 d . . . . .
H34A H 0.0285 0.7022 0.5744 0.059 Uiso 1 1 calc R U . . .
H34B H 0.1991 0.7628 0.5957 0.059 Uiso 1 1 calc R U . . .
C35 C 0.18577(17) 0.59340(15) 0.54948(4) 0.0513(3) Uani 1 1 d . . . . .
H35A H 0.1073 0.5043 0.5404 0.062 Uiso 1 1 calc R U . . .
H35B H 0.2780 0.5659 0.5615 0.062 Uiso 1 1 calc R U . . .
C36 C 0.23148(17) 0.68055(15) 0.50810(4) 0.0499(3) Uani 1 1 d . . . . .
H36A H 0.3094 0.7700 0.5172 0.060 Uiso 1 1 calc R U . . .
H36B H 0.1390 0.7075 0.4959 0.060 Uiso 1 1 calc R U . . .
C37 C 0.29806(17) 0.60034(15) 0.47111(4) 0.0512(3) Uani 1 1 d . . . . .
H37A H 0.3904 0.5733 0.4833 0.061 Uiso 1 1 calc R U . . .
H37B H 0.2201 0.5110 0.4620 0.061 Uiso 1 1 calc R U . . .
C38 C 0.34394(17) 0.68760(15) 0.42981(4) 0.0503(3) Uani 1 1 d . . . . .
H38A H 0.4214 0.7772 0.4390 0.060 Uiso 1 1 calc R U . . .
H38B H 0.2514 0.7141 0.4175 0.060 Uiso 1 1 calc R U . . .
C39 C 0.41153(17) 0.60758(15) 0.39295(4) 0.0518(4) Uani 1 1 d . . . . .
H39A H 0.5037 0.5807 0.4053 0.062 Uiso 1 1 calc R U . . .
H39B H 0.3338 0.5181 0.3838 0.062 Uiso 1 1 calc R U . . .
C40 C 0.45837(17) 0.69426(15) 0.35159(4) 0.0513(3) Uani 1 1 d . . . . .
H40A H 0.3661 0.7202 0.3389 0.062 Uiso 1 1 calc R U . . .
H40B H 0.5354 0.7842 0.3608 0.062 Uiso 1 1 calc R U . . .
C41 C 0.52727(18) 0.61365(15) 0.31530(5) 0.0539(4) Uani 1 1 d . . . . .
H41A H 0.6186 0.5866 0.3282 0.065 Uiso 1 1 calc R U . . .
H41B H 0.4496 0.5242 0.3060 0.065 Uiso 1 1 calc R U . . .
C42 C 0.57669(19) 0.69879(16) 0.27387(5) 0.0587(4) Uani 1 1 d . . . . .
H42A H 0.6533 0.7891 0.2830 0.070 Uiso 1 1 calc R U . . .
H42B H 0.4852 0.7239 0.2603 0.070 Uiso 1 1 calc R U . . .
C43 C 0.6480(2) 0.61514(19) 0.23882(5) 0.0742(5) Uani 1 1 d . . . . .
H43A H 0.7381 0.5890 0.2520 0.111 Uiso 1 1 calc R U . . .
H43B H 0.6802 0.6753 0.2138 0.111 Uiso 1 1 calc R U . . .
H43C H 0.5709 0.5282 0.2284 0.111 Uiso 1 1 calc R U . . .
C44 C -0.26268(19) 0.77318(18) 0.91376(5) 0.0613(4) Uani 1 1 d . . . . .
H44 H -0.1597 0.8167 0.9016 0.074 Uiso 1 1 calc R U . . .
C45 C -0.2506(3) 0.8021(2) 0.96393(5) 0.0892(6) Uani 1 1 d . . . . .
H45A H -0.1692 0.7608 0.9769 0.107 Uiso 1 1 calc R U . . .
H45B H -0.3501 0.7564 0.9769 0.107 Uiso 1 1 calc R U . . .
C46 C -0.2105(3) 0.9660(2) 0.97466(6) 0.0978(7) Uani 1 1 d . . . . .
H46A H -0.2126 0.9849 1.0070 0.117 Uiso 1 1 calc R U . . .
H46B H -0.1048 1.0095 0.9652 0.117 Uiso 1 1 calc R U . . .
C47 C -0.3271(2) 1.0346(2) 0.95091(6) 0.0859(6) Uani 1 1 d . . . . .
H47A H -0.4305 1.0014 0.9633 0.103 Uiso 1 1 calc R U . . .
H47B H -0.2940 1.1399 0.9554 0.103 Uiso 1 1 calc R U . . .
C48 C -0.3357(2) 0.99257(19) 0.90146(6) 0.0790(5) Uani 1 1 d . . . . .
H48A H -0.4140 1.0331 0.8865 0.095 Uiso 1 1 calc R U . . .
H48B H -0.2344 1.0335 0.8887 0.095 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 C20 1.4121(18) . ?
O1 C24 1.4291(19) . ?
O2 C44 1.4189(17) . ?
O2 C48 1.4331(19) . ?
N1 N2 1.3579(16) . ?
N1 C3 1.3579(17) . ?
N1 C20 1.4423(18) . ?
N2 C1 1.311(2) . ?
N3 N4 1.3576(17) . ?
N3 C27 1.3592(18) . ?
N3 C44 1.442(2) . ?
N4 C25 1.315(2) . ?
C1 C2 1.388(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.4911(19) . ?
C4 C5 1.5176(19) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.5130(18) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.5179(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.5158(18) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.5189(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.5175(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.5153(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.5174(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.5172(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.5174(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.5167(18) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.5178(18) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.5128(19) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.5144(19) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.502(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.500(2) . ?
C20 H20 0.9800 . ?
C21 C22 1.515(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.504(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.505(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.389(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.360(2) . ?
C26 H26 0.9300 . ?
C27 C28 1.492(2) . ?
C28 C29 1.5167(19) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.5140(19) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.5162(18) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.5142(18) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.5174(18) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.5159(18) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.5159(18) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.5171(18) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.5174(18) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.5158(18) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.5183(18) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.5161(18) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.5155(18) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C42 1.5142(19) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.519(2) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 C45 1.500(2) . ?
C44 H44 0.9800 . ?
C45 C46 1.522(3) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 C47 1.509(3) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 C48 1.500(2) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?

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
C20 O1 C24 111.40(12) . . ?
C44 O2 C48 111.38(12) . . ?
N2 N1 C3 112.17(12) . . ?
N2 N1 C20 120.37(12) . . ?
C3 N1 C20 127.41(11) . . ?
C1 N2 N1 103.86(13) . . ?
N4 N3 C27 112.46(14) . . ?
N4 N3 C44 120.74(13) . . ?
C27 N3 C44 126.69(13) . . ?
C25 N4 N3 103.75(14) . . ?
N2 C1 C2 112.71(15) . . ?
N2 C1 H1 123.6 . . ?
C2 C1 H1 123.6 . . ?
C3 C2 C1 105.21(15) . . ?
C3 C2 H2 127.4 . . ?
C1 C2 H2 127.4 . . ?
N1 C3 C2 106.05(13) . . ?
N1 C3 C4 123.19(13) . . ?
C2 C3 C4 130.76(14) . . ?
C3 C4 C5 112.52(12) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 114.17(12) . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 C7 113.39(11) . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C6 114.30(11) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C9 113.94(11) . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 114.07(11) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 114.13(11) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 114.01(11) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 114.27(11) . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 113.92(11) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 114.30(11) . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 113.79(11) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 114.67(11) . . ?
C17 C16 H16A 108.6 . . ?
C15 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 C18 113.98(12) . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 114.42(14) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 N1 105.86(11) . . ?
O1 C20 C21 111.82(13) . . ?
N1 C20 C21 113.37(12) . . ?
O1 C20 H20 108.5 . . ?
N1 C20 H20 108.5 . . ?
C21 C20 H20 108.5 . . ?
C20 C21 C22 109.92(14) . . ?
C20 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
C20 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
C23 C22 C21 110.28(16) . . ?
C23 C22 H22A 109.6 . . ?
C21 C22 H22A 109.6 . . ?
C23 C22 H22B 109.6 . . ?
C21 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C22 C23 C24 109.57(16) . . ?
C22 C23 H23A 109.8 . . ?
C24 C23 H23A 109.8 . . ?
C22 C23 H23B 109.8 . . ?
C24 C23 H23B 109.8 . . ?
H23A C23 H23B 108.2 . . ?
O1 C24 C23 111.12(15) . . ?
O1 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
O1 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
N4 C25 C26 112.43(17) . . ?
N4 C25 H25 123.8 . . ?
C26 C25 H25 123.8 . . ?
C27 C26 C25 105.59(16) . . ?
C27 C26 H26 127.2 . . ?
C25 C26 H26 127.2 . . ?
N3 C27 C26 105.77(14) . . ?
N3 C27 C28 121.86(14) . . ?
C26 C27 C28 132.34(14) . . ?
C27 C28 C29 113.89(13) . . ?
C27 C28 H28A 108.8 . . ?
C29 C28 H28A 108.8 . . ?
C27 C28 H28B 108.8 . . ?
C29 C28 H28B 108.8 . . ?
H28A C28 H28B 107.7 . . ?
C30 C29 C28 112.83(12) . . ?
C30 C29 H29A 109.0 . . ?
C28 C29 H29A 109.0 . . ?
C30 C29 H29B 109.0 . . ?
C28 C29 H29B 109.0 . . ?
H29A C29 H29B 107.8 . . ?
C29 C30 C31 113.89(12) . . ?
C29 C30 H30A 108.8 . . ?
C31 C30 H30A 108.8 . . ?
C29 C30 H30B 108.8 . . ?
C31 C30 H30B 108.8 . . ?
H30A C30 H30B 107.7 . . ?
C32 C31 C30 114.42(11) . . ?
C32 C31 H31A 108.7 . . ?
C30 C31 H31A 108.7 . . ?
C32 C31 H31B 108.7 . . ?
C30 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
C31 C32 C33 114.06(11) . . ?
C31 C32 H32A 108.7 . . ?
C33 C32 H32A 108.7 . . ?
C31 C32 H32B 108.7 . . ?
C33 C32 H32B 108.7 . . ?
H32A C32 H32B 107.6 . . ?
C34 C33 C32 114.19(11) . . ?
C34 C33 H33A 108.7 . . ?
C32 C33 H33A 108.7 . . ?
C34 C33 H33B 108.7 . . ?
C32 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?
C35 C34 C33 114.18(11) . . ?
C35 C34 H34A 108.7 . . ?
C33 C34 H34A 108.7 . . ?
C35 C34 H34B 108.7 . . ?
C33 C34 H34B 108.7 . . ?
H34A C34 H34B 107.6 . . ?
C34 C35 C36 114.17(11) . . ?
C34 C35 H35A 108.7 . . ?
C36 C35 H35A 108.7 . . ?
C34 C35 H35B 108.7 . . ?
C36 C35 H35B 108.7 . . ?
H35A C35 H35B 107.6 . . ?
C35 C36 C37 114.23(11) . . ?
C35 C36 H36A 108.7 . . ?
C37 C36 H36A 108.7 . . ?
C35 C36 H36B 108.7 . . ?
C37 C36 H36B 108.7 . . ?
H36A C36 H36B 107.6 . . ?
C38 C37 C36 114.18(11) . . ?
C38 C37 H37A 108.7 . . ?
C36 C37 H37A 108.7 . . ?
C38 C37 H37B 108.7 . . ?
C36 C37 H37B 108.7 . . ?
H37A C37 H37B 107.6 . . ?
C37 C38 C39 114.13(11) . . ?
C37 C38 H38A 108.7 . . ?
C39 C38 H38A 108.7 . . ?
C37 C38 H38B 108.7 . . ?
C39 C38 H38B 108.7 . . ?
H38A C38 H38B 107.6 . . ?
C40 C39 C38 114.50(11) . . ?
C40 C39 H39A 108.6 . . ?
C38 C39 H39A 108.6 . . ?
C40 C39 H39B 108.6 . . ?
C38 C39 H39B 108.6 . . ?
H39A C39 H39B 107.6 . . ?
C41 C40 C39 113.90(11) . . ?
C41 C40 H40A 108.8 . . ?
C39 C40 H40A 108.8 . . ?
C41 C40 H40B 108.8 . . ?
C39 C40 H40B 108.8 . . ?
H40A C40 H40B 107.7 . . ?
C42 C41 C40 114.84(12) . . ?
C42 C41 H41A 108.6 . . ?
C40 C41 H41A 108.6 . . ?
C42 C41 H41B 108.6 . . ?
C40 C41 H41B 108.6 . . ?
H41A C41 H41B 107.5 . . ?
C41 C42 C43 113.08(12) . . ?
C41 C42 H42A 109.0 . . ?
C43 C42 H42A 109.0 . . ?
C41 C42 H42B 109.0 . . ?
C43 C42 H42B 109.0 . . ?
H42A C42 H42B 107.8 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
O2 C44 N3 105.94(12) . . ?
O2 C44 C45 111.39(13) . . ?
N3 C44 C45 114.47(14) . . ?
O2 C44 H44 108.3 . . ?
N3 C44 H44 108.3 . . ?
C45 C44 H44 108.3 . . ?
C44 C45 C46 109.33(15) . . ?
C44 C45 H45A 109.8 . . ?
C46 C45 H45A 109.8 . . ?
C44 C45 H45B 109.8 . . ?
C46 C45 H45B 109.8 . . ?
H45A C45 H45B 108.3 . . ?
C47 C46 C45 110.61(17) . . ?
C47 C46 H46A 109.5 . . ?
C45 C46 H46A 109.5 . . ?
C47 C46 H46B 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 108.1 . . ?
C48 C47 C46 109.44(15) . . ?
C48 C47 H47A 109.8 . . ?
C46 C47 H47A 109.8 . . ?
C48 C47 H47B 109.8 . . ?
C46 C47 H47B 109.8 . . ?
H47A C47 H47B 108.2 . . ?
O2 C48 C47 111.52(15) . . ?
O2 C48 H48A 109.3 . . ?
C47 C48 H48A 109.3 . . ?
O2 C48 H48B 109.3 . . ?
C47 C48 H48B 109.3 . . ?
H48A C48 H48B 108.0 . . ?

_refine_diff_density_max         0.134
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.027

_shelxl_version_number           2014/6



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol, water'
