# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_d14137
_database_code_depnum_ccdc_archive 'CCDC 1404272'
_audit_update_record             
;
2015-06-01 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H27 Br N4 O'
_chemical_formula_sum            'C20 H27 Br N4 O'
_chemical_formula_weight         419.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   8.9698(4)
_cell_length_b                   18.4284(8)
_cell_length_c                   12.3981(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.310(2)
_cell_angle_gamma                90
_cell_volume                     2027.88(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    9115
_cell_measurement_theta_min      4.33
_cell_measurement_theta_max      67.01

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.882
_shelx_estimated_absorpt_T_min   0.570
_shelx_estimated_absorpt_T_max   0.625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39585
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.603
_diffrn_reflns_theta_max         67.191
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             7137
_reflns_number_gt                7079
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_max     0.972
_reflns_Friedel_fraction_full    0.961

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

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0400P)²+0.4954P] 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_abs_structure_details 
; 
 Flack x determined using 3350 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.016(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7137
_refine_ls_number_parameters     491
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0590
_refine_ls_wR_factor_gt          0.0588
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_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
Br1A Br 0.72100(3) 0.28229(2) 1.11177(2) 0.03198(10) Uani 1 1 d . . . . .
O1A O 0.0110(2) -0.05171(12) 1.21486(15) 0.0264(4) Uani 1 1 d . . . . .
N1A N 0.0641(2) 0.03001(12) 0.95643(16) 0.0187(4) Uani 1 1 d . . . . .
N2A N 0.2435(3) 0.13021(12) 1.09226(18) 0.0191(4) Uani 1 1 d . . . . .
N3A N 0.3372(3) 0.15142(14) 0.92237(19) 0.0223(5) Uani 1 1 d . . . . .
N4A N -0.1407(3) -0.04213(14) 1.05099(19) 0.0235(5) Uani 1 1 d . . . . .
C1A C 0.0746(3) 0.10933(14) 0.9357(2) 0.0182(5) Uani 1 1 d . . . . .
C2A C 0.0307(3) 0.11373(16) 0.8140(2) 0.0249(6) Uani 1 1 d . . . . .
H2AA H 0.0782 0.1561 0.7835 0.030 Uiso 1 1 calc R U . . .
H2AB H -0.0800 0.1171 0.7941 0.030 Uiso 1 1 calc R U . . .
C3A C 0.0911(5) 0.0421(2) 0.7734(2) 0.0416(8) Uani 1 1 d . . . . .
H3AA H 0.1780 0.0516 0.7344 0.050 Uiso 1 1 calc R U . . .
H3AB H 0.0116 0.0174 0.7228 0.050 Uiso 1 1 calc R U . . .
C4A C 0.1401(4) -0.00568(15) 0.8750(2) 0.0276(6) Uani 1 1 d . . . . .
H4AA H 0.1054 -0.0564 0.8627 0.033 Uiso 1 1 calc R U . . .
H4AB H 0.2508 -0.0052 0.8961 0.033 Uiso 1 1 calc R U . . .
C5A C 0.0997(3) 0.01835(14) 1.07423(19) 0.0181(5) Uani 1 1 d . . . . .
H5AA H 0.2024 -0.0035 1.0919 0.022 Uiso 1 1 calc R U . . .
C6A C 0.1023(3) 0.09835(14) 1.1150(2) 0.0191(5) Uani 1 1 d . . . . .
H6AA H 0.0810 0.1048 1.1914 0.023 Uiso 1 1 calc R U . . .
C7A C 0.2358(3) 0.13318(14) 0.9799(2) 0.0179(5) Uani 1 1 d . . . . .
C8A C -0.0090(3) 0.13672(15) 1.0267(2) 0.0219(5) Uani 1 1 d . . . . .
H8AA H -0.1132 0.1179 1.0215 0.026 Uiso 1 1 calc R U . . .
H8AB H -0.0077 0.1902 1.0339 0.026 Uiso 1 1 calc R U . . .
C9A C 0.4793(3) 0.17430(17) 0.9850(2) 0.0257(6) Uani 1 1 d . . . . .
H9AA H 0.5352 0.1311 1.0164 0.031 Uiso 1 1 calc R U . . .
H9AB H 0.4588 0.2056 1.0461 0.031 Uiso 1 1 calc R U . . .
C10A C 0.5751(3) 0.21543(17) 0.9149(2) 0.0250(6) Uani 1 1 d . . . . .
C11A C 0.6845(3) 0.26540(18) 0.9587(2) 0.0276(7) Uani 1 1 d . . . . .
C12A C 0.7710(3) 0.3044(2) 0.8948(3) 0.0394(8) Uani 1 1 d . . . . .
H12A H 0.8444 0.3380 0.9274 0.047 Uiso 1 1 calc R U . . .
C13A C 0.7495(4) 0.2940(2) 0.7839(3) 0.0502(10) Uani 1 1 d . . . . .
H13A H 0.8077 0.3205 0.7391 0.060 Uiso 1 1 calc R U . . .
C14A C 0.6423(4) 0.2446(2) 0.7380(3) 0.0469(9) Uani 1 1 d . . . . .
H14A H 0.6273 0.2369 0.6614 0.056 Uiso 1 1 calc R U . . .
C15A C 0.5569(4) 0.2062(2) 0.8032(3) 0.0342(7) Uani 1 1 d . . . . .
H15A H 0.4838 0.1726 0.7702 0.041 Uiso 1 1 calc R U . . .
C16A C -0.0154(3) -0.02924(15) 1.1198(2) 0.0196(5) Uani 1 1 d . . . . .
C17A C -0.2719(3) -0.08702(17) 1.0695(2) 0.0279(7) Uani 1 1 d . . . . .
C18A C -0.2203(4) -0.16541(18) 1.0882(3) 0.0378(7) Uani 1 1 d . . . . .
H18A H -0.1818 -0.1835 1.0232 0.057 Uiso 1 1 calc R U . . .
H18B H -0.3056 -0.1954 1.1024 0.057 Uiso 1 1 calc R U . . .
H18C H -0.1403 -0.1677 1.1510 0.057 Uiso 1 1 calc R U . . .
C19A C -0.3386(4) -0.0588(2) 1.1678(3) 0.0405(8) Uani 1 1 d . . . . .
H19A H -0.3701 -0.0083 1.1552 0.061 Uiso 1 1 calc R U . . .
H19B H -0.2625 -0.0617 1.2329 0.061 Uiso 1 1 calc R U . . .
H19C H -0.4260 -0.0885 1.1786 0.061 Uiso 1 1 calc R U . . .
C20A C -0.3855(4) -0.0805(3) 0.9670(3) 0.0541(11) Uani 1 1 d . . . . .
H20A H -0.4153 -0.0296 0.9557 0.081 Uiso 1 1 calc R U . . .
H20B H -0.4745 -0.1098 0.9747 0.081 Uiso 1 1 calc R U . . .
H20C H -0.3403 -0.0978 0.9044 0.081 Uiso 1 1 calc R U . . .
Br1B Br -0.23374(3) -0.22608(2) 0.37266(2) 0.02687(9) Uani 1 1 d . . . . .
O1B O 0.4938(2) 0.10380(11) 0.26022(14) 0.0240(4) Uani 1 1 d . . . . .
N1B N 0.4752(2) -0.01156(11) 0.49660(17) 0.0174(4) Uani 1 1 d . . . . .
N2B N 0.1618(2) -0.00053(12) 0.42496(18) 0.0174(4) Uani 1 1 d . . . . .
N3B N 0.1652(2) -0.09822(13) 0.55520(18) 0.0193(4) Uani 1 1 d . . . . .
N4B N 0.6486(2) 0.08927(14) 0.4213(2) 0.0198(5) Uani 1 1 d . . . . .
C1B C 0.3581(3) -0.00068(14) 0.5683(2) 0.0164(5) Uani 1 1 d . . . . .
C2B C 0.4347(3) -0.03060(15) 0.6761(2) 0.0224(6) Uani 1 1 d . . . . .
H2BA H 0.3600 -0.0495 0.7206 0.027 Uiso 1 1 calc R U . . .
H2BB H 0.4972 0.0069 0.7183 0.027 Uiso 1 1 calc R U . . .
C3B C 0.5340(3) -0.09298(17) 0.6399(2) 0.0294(6) Uani 1 1 d . . . . .
H3BA H 0.6388 -0.0886 0.6774 0.035 Uiso 1 1 calc R U . . .
H3BB H 0.4937 -0.1408 0.6579 0.035 Uiso 1 1 calc R U . . .
C4B C 0.5298(3) -0.08558(15) 0.5155(2) 0.0254(6) Uani 1 1 d . . . . .
H4BA H 0.6312 -0.0918 0.4942 0.031 Uiso 1 1 calc R U . . .
H4BB H 0.4598 -0.1211 0.4754 0.031 Uiso 1 1 calc R U . . .
C5B C 0.4189(3) 0.01947(14) 0.3896(2) 0.0171(5) Uani 1 1 d . . . . .
H5BA H 0.3943 -0.0198 0.3341 0.021 Uiso 1 1 calc R U . . .
C6B C 0.2720(3) 0.05690(13) 0.4156(2) 0.0164(5) Uani 1 1 d . . . . .
H6BA H 0.2347 0.0980 0.3662 0.020 Uiso 1 1 calc R U . . .
C7B C 0.2156(3) -0.04066(14) 0.5170(2) 0.0167(5) Uani 1 1 d . . . . .
C8B C 0.3147(3) 0.07741(13) 0.53722(19) 0.0170(5) Uani 1 1 d . . . . .
H8BA H 0.4004 0.1117 0.5506 0.020 Uiso 1 1 calc R U . . .
H8BB H 0.2283 0.0954 0.5710 0.020 Uiso 1 1 calc R U . . .
C9B C 0.0302(3) -0.12995(15) 0.4935(2) 0.0222(6) Uani 1 1 d . . . . .
H9BA H 0.0597 -0.1637 0.4380 0.027 Uiso 1 1 calc R U . . .
H9BB H -0.0323 -0.0910 0.4549 0.027 Uiso 1 1 calc R U . . .
C10B C -0.0613(3) -0.17060(14) 0.5674(2) 0.0176(5) Uani 1 1 d . . . . .
C11B C -0.1821(3) -0.21463(16) 0.52611(19) 0.0183(5) Uani 1 1 d . . . . .
C12B C -0.2691(3) -0.25078(15) 0.5927(2) 0.0232(6) Uani 1 1 d . . . . .
H12B H -0.3518 -0.2798 0.5617 0.028 Uiso 1 1 calc R U . . .
C13B C -0.2346(3) -0.24421(15) 0.7045(2) 0.0252(6) Uani 1 1 d . . . . .
H13B H -0.2928 -0.2690 0.7511 0.030 Uiso 1 1 calc R U . . .
C14B C -0.1140(3) -0.20102(15) 0.7483(2) 0.0242(6) Uani 1 1 d . . . . .
H14B H -0.0895 -0.1963 0.8251 0.029 Uiso 1 1 calc R U . . .
C15B C -0.0291(3) -0.16474(15) 0.6803(2) 0.0214(5) Uani 1 1 d . . . . .
H15B H 0.0528 -0.1352 0.7115 0.026 Uiso 1 1 calc R U . . .
C16B C 0.5264(3) 0.07511(15) 0.3506(2) 0.0185(5) Uani 1 1 d . . . . .
C17B C 0.7655(3) 0.14417(16) 0.4107(2) 0.0207(5) Uani 1 1 d . . . . .
C18B C 0.8442(3) 0.12620(16) 0.3129(2) 0.0251(6) Uani 1 1 d . . . . .
H18D H 0.8874 0.0774 0.3216 0.038 Uiso 1 1 calc R U . . .
H18E H 0.9247 0.1615 0.3082 0.038 Uiso 1 1 calc R U . . .
H18F H 0.7710 0.1282 0.2461 0.038 Uiso 1 1 calc R U . . .
C19B C 0.6930(3) 0.21952(16) 0.3987(2) 0.0249(6) Uani 1 1 d . . . . .
H19D H 0.6454 0.2303 0.4632 0.037 Uiso 1 1 calc R U . . .
H19E H 0.6167 0.2205 0.3336 0.037 Uiso 1 1 calc R U . . .
H19F H 0.7705 0.2560 0.3916 0.037 Uiso 1 1 calc R U . . .
C20B C 0.8775(3) 0.13966(18) 0.5150(3) 0.0298(6) Uani 1 1 d . . . . .
H20D H 0.9209 0.0908 0.5223 0.045 Uiso 1 1 calc R U . . .
H20E H 0.8258 0.1500 0.5777 0.045 Uiso 1 1 calc R U . . .
H20F H 0.9581 0.1752 0.5123 0.045 Uiso 1 1 calc R U . . .
H2NA H 0.316(4) 0.1194(17) 1.128(3) 0.015(8) Uiso 1 1 d . . . . .
H2NB H 0.113(4) -0.0192(18) 0.367(3) 0.021(8) Uiso 1 1 d . . . . .
H4NA H -0.144(4) -0.0216(19) 0.985(3) 0.025(8) Uiso 1 1 d . . . . .
H4NB H 0.659(4) 0.0707(19) 0.471(3) 0.014(8) 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
Br1A C11A 1.904(3) . ?
O1A C16A 1.240(3) . ?
N1A C4A 1.454(3) . ?
N1A C5A 1.465(3) . ?
N1A C1A 1.490(3) . ?
N2A C7A 1.386(3) . ?
N2A C6A 1.460(3) . ?
N2A H2NA 0.76(4) . ?
N3A C7A 1.279(4) . ?
N3A C9A 1.456(4) . ?
N4A C16A 1.331(4) . ?
N4A C17A 1.483(4) . ?
N4A H4NA 0.89(4) . ?
C1A C2A 1.505(4) . ?
C1A C8A 1.529(4) . ?
C1A C7A 1.535(4) . ?
C2A C3A 1.539(4) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C3A C4A 1.548(4) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C5A C16A 1.524(4) . ?
C5A C6A 1.558(3) . ?
C5A H5AA 1.0000 . ?
C6A C8A 1.542(4) . ?
C6A H6AA 1.0000 . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A C10A 1.512(4) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A C15A 1.381(4) . ?
C10A C11A 1.397(4) . ?
C11A C12A 1.387(4) . ?
C12A C13A 1.374(5) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.386(6) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.385(5) . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9500 . ?
C17A C20A 1.514(5) . ?
C17A C18A 1.524(5) . ?
C17A C19A 1.525(4) . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
Br1B C11B 1.904(2) . ?
O1B C16B 1.235(3) . ?
N1B C4B 1.457(3) . ?
N1B C5B 1.466(3) . ?
N1B C1B 1.485(3) . ?
N2B C7B 1.386(3) . ?
N2B C6B 1.464(3) . ?
N2B H2NB 0.85(4) . ?
N3B C7B 1.271(4) . ?
N3B C9B 1.458(3) . ?
N4B C16B 1.327(4) . ?
N4B C17B 1.477(4) . ?
N4B H4NB 0.70(4) . ?
C1B C2B 1.515(4) . ?
C1B C8B 1.526(3) . ?
C1B C7B 1.532(3) . ?
C2B C3B 1.560(4) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C3B C4B 1.543(4) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C5B C16B 1.533(4) . ?
C5B C6B 1.561(3) . ?
C5B H5BA 1.0000 . ?
C6B C8B 1.548(3) . ?
C6B H6BA 1.0000 . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B C10B 1.514(4) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10B C11B 1.391(4) . ?
C10B C15B 1.392(4) . ?
C11B C12B 1.386(4) . ?
C12B C13B 1.381(4) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.388(4) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.386(4) . ?
C14B H14B 0.9500 . ?
C15B H15B 0.9500 . ?
C17B C20B 1.521(4) . ?
C17B C18B 1.524(4) . ?
C17B C19B 1.531(4) . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4A N1A C5A 124.7(2) . . ?
C4A N1A C1A 106.02(19) . . ?
C5A N1A C1A 107.83(19) . . ?
C7A N2A C6A 106.9(2) . . ?
C7A N2A H2NA 121(2) . . ?
C6A N2A H2NA 118(2) . . ?
C7A N3A C9A 114.6(2) . . ?
C16A N4A C17A 128.0(2) . . ?
C16A N4A H4NA 115(2) . . ?
C17A N4A H4NA 117(2) . . ?
N1A C1A C2A 102.2(2) . . ?
N1A C1A C8A 98.4(2) . . ?
C2A C1A C8A 129.6(2) . . ?
N1A C1A C7A 107.4(2) . . ?
C2A C1A C7A 116.0(2) . . ?
C8A C1A C7A 100.3(2) . . ?
C1A C2A C3A 103.2(2) . . ?
C1A C2A H2AA 111.1 . . ?
C3A C2A H2AA 111.1 . . ?
C1A C2A H2AB 111.1 . . ?
C3A C2A H2AB 111.1 . . ?
H2AA C2A H2AB 109.1 . . ?
C2A C3A C4A 107.1(2) . . ?
C2A C3A H3AA 110.3 . . ?
C4A C3A H3AA 110.3 . . ?
C2A C3A H3AB 110.3 . . ?
C4A C3A H3AB 110.3 . . ?
H3AA C3A H3AB 108.6 . . ?
N1A C4A C3A 101.6(2) . . ?
N1A C4A H4AA 111.4 . . ?
C3A C4A H4AA 111.4 . . ?
N1A C4A H4AB 111.4 . . ?
C3A C4A H4AB 111.4 . . ?
H4AA C4A H4AB 109.3 . . ?
N1A C5A C16A 113.1(2) . . ?
N1A C5A C6A 100.10(19) . . ?
C16A C5A C6A 113.8(2) . . ?
N1A C5A H5AA 109.8 . . ?
C16A C5A H5AA 109.8 . . ?
C6A C5A H5AA 109.8 . . ?
N2A C6A C8A 99.7(2) . . ?
N2A C6A C5A 106.90(19) . . ?
C8A C6A C5A 103.06(19) . . ?
N2A C6A H6AA 115.1 . . ?
C8A C6A H6AA 115.1 . . ?
C5A C6A H6AA 115.1 . . ?
N3A C7A N2A 129.4(2) . . ?
N3A C7A C1A 125.8(2) . . ?
N2A C7A C1A 104.8(2) . . ?
C1A C8A C6A 92.08(19) . . ?
C1A C8A H8AA 113.3 . . ?
C6A C8A H8AA 113.3 . . ?
C1A C8A H8AB 113.3 . . ?
C6A C8A H8AB 113.3 . . ?
H8AA C8A H8AB 110.6 . . ?
N3A C9A C10A 111.4(2) . . ?
N3A C9A H9AA 109.3 . . ?
C10A C9A H9AA 109.3 . . ?
N3A C9A H9AB 109.3 . . ?
C10A C9A H9AB 109.3 . . ?
H9AA C9A H9AB 108.0 . . ?
C15A C10A C11A 116.5(3) . . ?
C15A C10A C9A 121.4(3) . . ?
C11A C10A C9A 122.2(3) . . ?
C12A C11A C10A 122.6(3) . . ?
C12A C11A Br1A 117.0(2) . . ?
C10A C11A Br1A 120.3(2) . . ?
C13A C12A C11A 119.3(3) . . ?
C13A C12A H12A 120.3 . . ?
C11A C12A H12A 120.3 . . ?
C12A C13A C14A 119.5(3) . . ?
C12A C13A H13A 120.3 . . ?
C14A C13A H13A 120.3 . . ?
C15A C14A C13A 120.3(3) . . ?
C15A C14A H14A 119.8 . . ?
C13A C14A H14A 119.8 . . ?
C10A C15A C14A 121.8(3) . . ?
C10A C15A H15A 119.1 . . ?
C14A C15A H15A 119.1 . . ?
O1A C16A N4A 125.3(3) . . ?
O1A C16A C5A 119.9(2) . . ?
N4A C16A C5A 114.8(2) . . ?
N4A C17A C20A 106.2(3) . . ?
N4A C17A C18A 108.8(3) . . ?
C20A C17A C18A 110.9(3) . . ?
N4A C17A C19A 110.2(3) . . ?
C20A C17A C19A 110.5(3) . . ?
C18A C17A C19A 110.3(3) . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C17A C19A H19A 109.5 . . ?
C17A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C17A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C17A C20A H20A 109.5 . . ?
C17A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C17A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C4B N1B C5B 125.1(2) . . ?
C4B N1B C1B 106.31(19) . . ?
C5B N1B C1B 107.98(19) . . ?
C7B N2B C6B 107.0(2) . . ?
C7B N2B H2NB 123(2) . . ?
C6B N2B H2NB 120(2) . . ?
C7B N3B C9B 116.9(2) . . ?
C16B N4B C17B 127.3(3) . . ?
C16B N4B H4NB 119(3) . . ?
C17B N4B H4NB 114(3) . . ?
N1B C1B C2B 102.1(2) . . ?
N1B C1B C8B 98.78(19) . . ?
C2B C1B C8B 129.3(2) . . ?
N1B C1B C7B 107.8(2) . . ?
C2B C1B C7B 115.9(2) . . ?
C8B C1B C7B 100.45(19) . . ?
C1B C2B C3B 102.7(2) . . ?
C1B C2B H2BA 111.2 . . ?
C3B C2B H2BA 111.2 . . ?
C1B C2B H2BB 111.2 . . ?
C3B C2B H2BB 111.2 . . ?
H2BA C2B H2BB 109.1 . . ?
C4B C3B C2B 106.9(2) . . ?
C4B C3B H3BA 110.4 . . ?
C2B C3B H3BA 110.4 . . ?
C4B C3B H3BB 110.4 . . ?
C2B C3B H3BB 110.4 . . ?
H3BA C3B H3BB 108.6 . . ?
N1B C4B C3B 101.7(2) . . ?
N1B C4B H4BA 111.4 . . ?
C3B C4B H4BA 111.4 . . ?
N1B C4B H4BB 111.4 . . ?
C3B C4B H4BB 111.4 . . ?
H4BA C4B H4BB 109.3 . . ?
N1B C5B C16B 113.3(2) . . ?
N1B C5B C6B 100.13(18) . . ?
C16B C5B C6B 111.0(2) . . ?
N1B C5B H5BA 110.7 . . ?
C16B C5B H5BA 110.7 . . ?
C6B C5B H5BA 110.7 . . ?
N2B C6B C8B 100.02(18) . . ?
N2B C6B C5B 107.24(19) . . ?
C8B C6B C5B 102.23(19) . . ?
N2B C6B H6BA 115.2 . . ?
C8B C6B H6BA 115.2 . . ?
C5B C6B H6BA 115.2 . . ?
N3B C7B N2B 130.7(2) . . ?
N3B C7B C1B 124.5(2) . . ?
N2B C7B C1B 104.8(2) . . ?
C1B C8B C6B 91.96(18) . . ?
C1B C8B H8BA 113.3 . . ?
C6B C8B H8BA 113.3 . . ?
C1B C8B H8BB 113.3 . . ?
C6B C8B H8BB 113.3 . . ?
H8BA C8B H8BB 110.6 . . ?
N3B C9B C10B 111.2(2) . . ?
N3B C9B H9BA 109.4 . . ?
C10B C9B H9BA 109.4 . . ?
N3B C9B H9BB 109.4 . . ?
C10B C9B H9BB 109.4 . . ?
H9BA C9B H9BB 108.0 . . ?
C11B C10B C15B 116.9(2) . . ?
C11B C10B C9B 121.8(2) . . ?
C15B C10B C9B 121.3(2) . . ?
C12B C11B C10B 122.5(2) . . ?
C12B C11B Br1B 117.7(2) . . ?
C10B C11B Br1B 119.80(19) . . ?
C13B C12B C11B 119.5(3) . . ?
C13B C12B H12B 120.3 . . ?
C11B C12B H12B 120.3 . . ?
C12B C13B C14B 119.4(2) . . ?
C12B C13B H13B 120.3 . . ?
C14B C13B H13B 120.3 . . ?
C15B C14B C13B 120.3(2) . . ?
C15B C14B H14B 119.8 . . ?
C13B C14B H14B 119.8 . . ?
C14B C15B C10B 121.4(3) . . ?
C14B C15B H15B 119.3 . . ?
C10B C15B H15B 119.3 . . ?
O1B C16B N4B 125.4(2) . . ?
O1B C16B C5B 119.7(2) . . ?
N4B C16B C5B 114.9(2) . . ?
N4B C17B C20B 106.1(2) . . ?
N4B C17B C18B 109.8(2) . . ?
C20B C17B C18B 109.8(2) . . ?
N4B C17B C19B 109.4(2) . . ?
C20B C17B C19B 110.6(2) . . ?
C18B C17B C19B 111.0(2) . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C17B C19B H19D 109.5 . . ?
C17B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C17B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C17B C20B H20D 109.5 . . ?
C17B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C17B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4A N1A C1A C2A 46.3(3) . . . . ?
C5A N1A C1A C2A -178.1(2) . . . . ?
C4A N1A C1A C8A -180.0(2) . . . . ?
C5A N1A C1A C8A -44.4(2) . . . . ?
C4A N1A C1A C7A -76.3(2) . . . . ?
C5A N1A C1A C7A 59.3(2) . . . . ?
N1A C1A C2A C3A -32.8(3) . . . . ?
C8A C1A C2A C3A -144.8(3) . . . . ?
C7A C1A C2A C3A 83.7(3) . . . . ?
C1A C2A C3A C4A 10.3(3) . . . . ?
C5A N1A C4A C3A -164.4(3) . . . . ?
C1A N1A C4A C3A -38.5(3) . . . . ?
C2A C3A C4A N1A 16.8(3) . . . . ?
C4A N1A C5A C16A -104.1(3) . . . . ?
C1A N1A C5A C16A 130.8(2) . . . . ?
C4A N1A C5A C6A 134.5(2) . . . . ?
C1A N1A C5A C6A 9.3(2) . . . . ?
C7A N2A C6A C8A -40.8(2) . . . . ?
C7A N2A C6A C5A 66.2(3) . . . . ?
N1A C5A C6A N2A -75.7(2) . . . . ?
C16A C5A C6A N2A 163.4(2) . . . . ?
N1A C5A C6A C8A 28.9(2) . . . . ?
C16A C5A C6A C8A -92.0(2) . . . . ?
C9A N3A C7A N2A -2.0(4) . . . . ?
C9A N3A C7A C1A 177.9(2) . . . . ?
C6A N2A C7A N3A -173.8(3) . . . . ?
C6A N2A C7A C1A 6.3(3) . . . . ?
N1A C1A C7A N3A 108.6(3) . . . . ?
C2A C1A C7A N3A -5.0(4) . . . . ?
C8A C1A C7A N3A -149.1(3) . . . . ?
N1A C1A C7A N2A -71.4(2) . . . . ?
C2A C1A C7A N2A 174.9(2) . . . . ?
C8A C1A C7A N2A 30.8(3) . . . . ?
N1A C1A C8A C6A 57.8(2) . . . . ?
C2A C1A C8A C6A 171.4(3) . . . . ?
C7A C1A C8A C6A -51.8(2) . . . . ?
N2A C6A C8A C1A 56.2(2) . . . . ?
C5A C6A C8A C1A -53.8(2) . . . . ?
C7A N3A C9A C10A -163.1(2) . . . . ?
N3A C9A C10A C15A -23.7(4) . . . . ?
N3A C9A C10A C11A 155.2(3) . . . . ?
C15A C10A C11A C12A 0.2(4) . . . . ?
C9A C10A C11A C12A -178.8(3) . . . . ?
C15A C10A C11A Br1A -179.5(2) . . . . ?
C9A C10A C11A Br1A 1.5(4) . . . . ?
C10A C11A C12A C13A -0.1(5) . . . . ?
Br1A C11A C12A C13A 179.7(3) . . . . ?
C11A C12A C13A C14A -0.2(6) . . . . ?
C12A C13A C14A C15A 0.3(6) . . . . ?
C11A C10A C15A C14A -0.1(5) . . . . ?
C9A C10A C15A C14A 178.9(3) . . . . ?
C13A C14A C15A C10A -0.1(6) . . . . ?
C17A N4A C16A O1A -2.4(5) . . . . ?
C17A N4A C16A C5A 178.8(3) . . . . ?
N1A C5A C16A O1A 170.2(2) . . . . ?
C6A C5A C16A O1A -76.5(3) . . . . ?
N1A C5A C16A N4A -10.9(3) . . . . ?
C6A C5A C16A N4A 102.4(3) . . . . ?
C16A N4A C17A C20A 177.5(3) . . . . ?
C16A N4A C17A C18A -63.2(4) . . . . ?
C16A N4A C17A C19A 57.9(4) . . . . ?
C4B N1B C1B C2B 47.0(3) . . . . ?
C5B N1B C1B C2B -176.6(2) . . . . ?
C4B N1B C1B C8B -179.6(2) . . . . ?
C5B N1B C1B C8B -43.2(2) . . . . ?
C4B N1B C1B C7B -75.5(2) . . . . ?
C5B N1B C1B C7B 60.9(2) . . . . ?
N1B C1B C2B C3B -32.9(2) . . . . ?
C8B C1B C2B C3B -145.0(3) . . . . ?
C7B C1B C2B C3B 83.9(3) . . . . ?
C1B C2B C3B C4B 10.0(3) . . . . ?
C5B N1B C4B C3B -166.2(2) . . . . ?
C1B N1B C4B C3B -39.4(3) . . . . ?
C2B C3B C4B N1B 17.2(3) . . . . ?
C4B N1B C5B C16B -108.4(3) . . . . ?
C1B N1B C5B C16B 125.6(2) . . . . ?
C4B N1B C5B C6B 133.4(2) . . . . ?
C1B N1B C5B C6B 7.4(2) . . . . ?
C7B N2B C6B C8B -39.2(2) . . . . ?
C7B N2B C6B C5B 67.1(2) . . . . ?
N1B C5B C6B N2B -74.1(2) . . . . ?
C16B C5B C6B N2B 165.9(2) . . . . ?
N1B C5B C6B C8B 30.6(2) . . . . ?
C16B C5B C6B C8B -89.4(2) . . . . ?
C9B N3B C7B N2B 1.4(4) . . . . ?
C9B N3B C7B C1B -178.2(2) . . . . ?
C6B N2B C7B N3B -175.1(3) . . . . ?
C6B N2B C7B C1B 4.5(2) . . . . ?
N1B C1B C7B N3B 109.2(3) . . . . ?
C2B C1B C7B N3B -4.4(4) . . . . ?
C8B C1B C7B N3B -148.0(2) . . . . ?
N1B C1B C7B N2B -70.5(2) . . . . ?
C2B C1B C7B N2B 175.9(2) . . . . ?
C8B C1B C7B N2B 32.3(2) . . . . ?
N1B C1B C8B C6B 57.89(19) . . . . ?
C2B C1B C8B C6B 171.4(2) . . . . ?
C7B C1B C8B C6B -52.2(2) . . . . ?
N2B C6B C8B C1B 55.5(2) . . . . ?
C5B C6B C8B C1B -54.8(2) . . . . ?
C7B N3B C9B C10B -151.1(2) . . . . ?
N3B C9B C10B C11B -170.0(2) . . . . ?
N3B C9B C10B C15B 10.8(4) . . . . ?
C15B C10B C11B C12B 0.8(4) . . . . ?
C9B C10B C11B C12B -178.4(3) . . . . ?
C15B C10B C11B Br1B -179.79(19) . . . . ?
C9B C10B C11B Br1B 1.0(4) . . . . ?
C10B C11B C12B C13B -1.0(4) . . . . ?
Br1B C11B C12B C13B 179.6(2) . . . . ?
C11B C12B C13B C14B 0.5(4) . . . . ?
C12B C13B C14B C15B 0.1(4) . . . . ?
C13B C14B C15B C10B -0.3(4) . . . . ?
C11B C10B C15B C14B -0.2(4) . . . . ?
C9B C10B C15B C14B 179.0(2) . . . . ?
C17B N4B C16B O1B 3.8(4) . . . . ?
C17B N4B C16B C5B -174.7(2) . . . . ?
N1B C5B C16B O1B 178.1(2) . . . . ?
C6B C5B C16B O1B -70.2(3) . . . . ?
N1B C5B C16B N4B -3.4(3) . . . . ?
C6B C5B C16B N4B 108.4(3) . . . . ?
C16B N4B C17B C20B 178.3(3) . . . . ?
C16B N4B C17B C18B -63.0(3) . . . . ?
C16B N4B C17B C19B 59.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4A H4NA N1A 0.89(4) 2.17(3) 2.672(3) 115(3) .
N4B H4NB N1B 0.70(4) 2.30(3) 2.677(3) 116(3) .
N2B H2NB O1A 0.85(4) 2.07(4) 2.913(3) 171(3) 1_554
N2A H2NA O1B 0.76(4) 2.13(4) 2.874(3) 165(3) 1_556

_refine_diff_density_max         0.495
_refine_diff_density_min         -0.868
_refine_diff_density_rms         0.056

_shelxl_version_number           2014/6



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# 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 
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data_d13160_sq_d
_database_code_depnum_ccdc_archive 'CCDC 1404273'
_audit_update_record             
;
2015-06-01 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H51 N7 O6, H2 O'
_chemical_formula_sum            'C33 H53 N7 O7'
_chemical_formula_weight         659.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   10.0804(3)
_cell_length_b                   9.9982(3)
_cell_length_c                   19.7575(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.2990(17)
_cell_angle_gamma                90
_cell_volume                     1937.88(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    9091
_cell_measurement_theta_min      4.51
_cell_measurement_theta_max      65.61

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.654
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7079
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36769
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.298
_diffrn_reflns_theta_max         66.745
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.946
_reflns_number_total             6593
_reflns_number_gt                6365
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_max     0.938
_reflns_Friedel_fraction_full    0.923

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.

 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0522P)²+0.6512P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2813 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6593
_refine_ls_number_parameters     425
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.7232(3) 0.2290(4) 0.59986(16) 0.0933(13) Uani 1 1 d . . . . .
O2 O 0.9269(3) 0.3352(2) 0.82459(12) 0.0546(6) Uani 1 1 d . . . . .
O3 O 1.0819(2) 0.7892(2) 0.80477(14) 0.0531(6) Uani 1 1 d . . . . .
O4 O 0.8325(2) 0.6976(2) 0.64224(11) 0.0447(5) Uani 1 1 d . . . . .
O5 O 0.5819(2) 0.6668(2) 0.77210(10) 0.0368(5) Uani 1 1 d . . . . .
O6 O 0.2933(3) 0.3577(4) 0.59810(15) 0.0754(9) Uani 1 1 d . . . . .
N1 N 0.6455(3) 0.3284(3) 0.68413(13) 0.0408(6) Uani 1 1 d . . . . .
H1N H 0.6858 0.3446 0.7289 0.061 Uiso 1 1 d R U . . .
N2 N 0.8901(3) 0.4661(2) 0.73003(13) 0.0356(6) Uani 1 1 d . . . . .
H2N H 0.8679 0.5483 0.7125 0.053 Uiso 1 1 d R U . . .
N3 N 0.8810(2) 0.6911(2) 0.80643(12) 0.0317(5) Uani 1 1 d . . . . .
H3N H 0.7894 0.6921 0.7928 0.048 Uiso 1 1 d R U . . .
N4 N 0.7496(3) 0.8604(3) 0.70005(12) 0.0402(6) Uani 1 1 d . . . . .
H4N H 0.6772 0.9035 0.7092 0.060 Uiso 1 1 d R U . . .
N5 N 0.4875(3) 0.8121(3) 0.63662(12) 0.0441(6) Uani 1 1 d . . . . .
N6 N 0.4387(3) 0.8242(3) 0.79830(12) 0.0432(6) Uani 1 1 d . . . . .
H6N H 0.3499 0.8416 0.7806 0.065 Uiso 1 1 d R U . . .
N7 N 0.4258(3) 0.5034(3) 0.66955(13) 0.0424(6) Uani 1 1 d . . . . .
H7N H 0.4960 0.5137 0.7066 0.064 Uiso 1 1 d R U . . .
C1 C 0.7435(3) 0.2998(3) 0.65187(15) 0.0389(7) Uani 1 1 d . . . . .
C2 C 0.8835(3) 0.3578(3) 0.68108(16) 0.0402(7) Uani 1 1 d . . . . .
H2A H 0.9437 0.2849 0.7042 0.048 Uiso 1 1 calc R U . . .
H2B H 0.9206 0.3900 0.6418 0.048 Uiso 1 1 calc R U . . .
C3 C 0.9176(3) 0.4466(3) 0.79875(15) 0.0335(6) Uani 1 1 d . . . . .
C4 C 0.8908(3) 0.5527(3) 0.91121(14) 0.0347(6) Uani 1 1 d . . . . .
H4A H 0.9164 0.4616 0.9292 0.042 Uiso 1 1 calc R U . . .
H4B H 0.7900 0.5579 0.8996 0.042 Uiso 1 1 calc R U . . .
C5 C 0.9463(3) 0.6537(3) 0.96914(16) 0.0406(7) Uani 1 1 d . . . . .
H5A H 0.9247 0.7458 0.9500 0.049 Uiso 1 1 calc R U . . .
C6 C 0.8747(4) 0.6331(4) 1.02894(17) 0.0541(9) Uani 1 1 d . . . . .
H6A H 0.9103 0.6975 1.0661 0.081 Uiso 1 1 calc R U . . .
H6B H 0.8917 0.5420 1.0471 0.081 Uiso 1 1 calc R U . . .
H6C H 0.7764 0.6468 1.0118 0.081 Uiso 1 1 calc R U . . .
C7 C 1.0986(4) 0.6427(5) 0.9955(2) 0.0633(11) Uani 1 1 d . . . . .
H7A H 1.1297 0.7091 1.0322 0.095 Uiso 1 1 calc R U . . .
H7B H 1.1433 0.6589 0.9572 0.095 Uiso 1 1 calc R U . . .
H7C H 1.1218 0.5528 1.0143 0.095 Uiso 1 1 calc R U . . .
C8 C 0.9407(3) 0.5725(3) 0.84493(14) 0.0324(6) Uani 1 1 d . . . . .
H8A H 1.0414 0.5875 0.8591 0.039 Uiso 1 1 calc R U . . .
C9 C 0.9574(3) 0.7874(3) 0.78658(15) 0.0388(7) Uani 1 1 d . . . . .
C10 C 0.8832(4) 0.8990(3) 0.74040(15) 0.0402(7) Uani 1 1 d . . . . .
H10A H 0.9397 0.9226 0.7066 0.048 Uiso 1 1 calc R U . . .
C11 C 0.8745(4) 1.0230(3) 0.78341(19) 0.0483(8) Uani 1 1 d . . . . .
H11A H 0.8275 1.0942 0.7531 0.073 Uiso 1 1 calc R U . . .
H11B H 0.9667 1.0528 0.8060 0.073 Uiso 1 1 calc R U . . .
H11C H 0.8239 1.0021 0.8189 0.073 Uiso 1 1 calc R U . . .
C12 C 0.7344(3) 0.7625(3) 0.65300(14) 0.0397(7) Uani 1 1 d . . . . .
C13 C 0.5911(3) 0.7316(3) 0.61303(14) 0.0397(7) Uani 1 1 d . . . . .
H13A H 0.5717 0.6344 0.6177 0.048 Uiso 1 1 calc R U . . .
C14 C 0.5730(4) 0.7674(3) 0.53487(15) 0.0472(8) Uani 1 1 d . . . . .
H14A H 0.6619 0.7711 0.5217 0.057 Uiso 1 1 calc R U . . .
H14B H 0.5133 0.7020 0.5047 0.057 Uiso 1 1 calc R U . . .
C15 C 0.5068(4) 0.9045(4) 0.53023(16) 0.0550(10) Uani 1 1 d . . . . .
H15A H 0.5748 0.9752 0.5476 0.066 Uiso 1 1 calc R U . . .
H15B H 0.4585 0.9258 0.4819 0.066 Uiso 1 1 calc R U . . .
C16 C 0.4088(4) 0.8889(4) 0.57644(16) 0.0546(9) Uani 1 1 d . . . . .
H16A H 0.3811 0.9771 0.5913 0.066 Uiso 1 1 calc R U . . .
H16B H 0.3264 0.8392 0.5525 0.066 Uiso 1 1 calc R U . . .
C17 C 0.4015(3) 0.7502(4) 0.67946(16) 0.0472(8) Uani 1 1 d . . . . .
H17A H 0.3262 0.8154 0.6793 0.057 Uiso 1 1 calc R U . . .
C18 C 0.4830(3) 0.7428(3) 0.75520(14) 0.0383(7) Uani 1 1 d . . . . .
C19 C 0.4856(3) 0.8312(3) 0.87551(14) 0.0365(7) Uani 1 1 d . . . . .
C20 C 0.6319(3) 0.8809(3) 0.89416(15) 0.0417(7) Uani 1 1 d . . . . .
H20A H 0.6367 0.9696 0.8737 0.063 Uiso 1 1 calc R U . . .
H20B H 0.6902 0.8186 0.8759 0.063 Uiso 1 1 calc R U . . .
H20C H 0.6632 0.8867 0.9448 0.063 Uiso 1 1 calc R U . . .
C21 C 0.3921(4) 0.9309(4) 0.89946(17) 0.0471(8) Uani 1 1 d . . . . .
H21A H 0.2980 0.8980 0.8869 0.071 Uiso 1 1 calc R U . . .
H21B H 0.3975 1.0174 0.8769 0.071 Uiso 1 1 calc R U . . .
H21C H 0.4203 0.9417 0.9500 0.071 Uiso 1 1 calc R U . . .
C22 C 0.4723(4) 0.6941(3) 0.90612(17) 0.0469(8) Uani 1 1 d . . . . .
H22A H 0.3769 0.6651 0.8930 0.070 Uiso 1 1 calc R U . . .
H22B H 0.5019 0.6985 0.9569 0.070 Uiso 1 1 calc R U . . .
H22C H 0.5294 0.6300 0.8882 0.070 Uiso 1 1 calc R U . . .
C23 C 0.3311(4) 0.6170(4) 0.65458(17) 0.0518(9) Uani 1 1 d . . . . .
H23A H 0.2963 0.6225 0.6030 0.062 Uiso 1 1 calc R U . . .
C24 C 0.2100(4) 0.5952(6) 0.6866(2) 0.0732(13) Uani 1 1 d . . . . .
H24A H 0.1670 0.5092 0.6709 0.110 Uiso 1 1 calc R U . . .
H24B H 0.1439 0.6675 0.6723 0.110 Uiso 1 1 calc R U . . .
H24C H 0.2408 0.5946 0.7374 0.110 Uiso 1 1 calc R U . . .
C25 C 0.3995(3) 0.3854(4) 0.63973(17) 0.0499(9) Uani 1 1 d . . . . .
C26 C 0.5085(3) 0.2756(4) 0.66044(17) 0.0483(8) Uani 1 1 d . . . . .
H26A H 0.5081 0.2235 0.6172 0.058 Uiso 1 1 calc R U . . .
C27 C 0.4687(4) 0.1763(4) 0.71233(18) 0.0511(9) Uani 1 1 d . . . . .
H27A H 0.3818 0.1325 0.6896 0.061 Uiso 1 1 calc R U . . .
H27B H 0.5393 0.1058 0.7234 0.061 Uiso 1 1 calc R U . . .
C28 C 0.4524(3) 0.2395(3) 0.77965(16) 0.0413(7) Uani 1 1 d . . . . .
C29 C 0.5625(3) 0.2632(3) 0.83395(17) 0.0418(7) Uani 1 1 d . . . . .
H29A H 0.6515 0.2400 0.8294 0.050 Uiso 1 1 calc R U . . .
C30 C 0.5449(4) 0.3208(3) 0.89567(16) 0.0459(8) Uani 1 1 d . . . . .
H30A H 0.6215 0.3386 0.9327 0.055 Uiso 1 1 calc R U . . .
C31 C 0.4159(4) 0.3517(4) 0.90237(16) 0.0480(8) Uani 1 1 d . . . . .
H31A H 0.4031 0.3893 0.9446 0.058 Uiso 1 1 calc R U . . .
C32 C 0.3055(4) 0.3286(4) 0.84855(18) 0.0505(8) Uani 1 1 d . . . . .
H32A H 0.2167 0.3506 0.8537 0.061 Uiso 1 1 calc R U . . .
C33 C 0.3223(3) 0.2734(4) 0.78671(17) 0.0483(8) Uani 1 1 d . . . . .
H33A H 0.2454 0.2587 0.7494 0.058 Uiso 1 1 calc R U . . .
O1W O 0.2092(3) 0.9725(4) 0.7366(3) 0.1088(15) Uani 1 1 d . . . . .
H1WA H 0.1702 0.9152 0.7566 0.163 Uiso 1 1 d R U . . .
H1WB H 0.1670 1.0200 0.7035 0.163 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.225(4) . ?
O2 C3 1.220(4) . ?
O3 C9 1.223(4) . ?
O4 C12 1.241(4) . ?
O5 C18 1.237(4) . ?
O6 C25 1.222(4) . ?
N1 C1 1.324(4) . ?
N1 C26 1.451(4) . ?
N1 H1N 0.9000 . ?
N2 C3 1.336(4) . ?
N2 C2 1.443(4) . ?
N2 H2N 0.9000 . ?
N3 C9 1.346(4) . ?
N3 C8 1.462(3) . ?
N3 H3N 0.9000 . ?
N4 C12 1.334(4) . ?
N4 C10 1.451(4) . ?
N4 H4N 0.9000 . ?
N5 C13 1.476(4) . ?
N5 C17 1.479(5) . ?
N5 C16 1.483(4) . ?
N6 C18 1.327(4) . ?
N6 C19 1.491(3) . ?
N6 H6N 0.9000 . ?
N7 C25 1.318(5) . ?
N7 C23 1.470(5) . ?
N7 H7N 0.9000 . ?
C1 C2 1.512(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.540(4) . ?
C4 C8 1.520(4) . ?
C4 C5 1.533(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C7 1.507(5) . ?
C5 C6 1.534(5) . ?
C5 H5A 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 1.0000 . ?
C9 C10 1.523(4) . ?
C10 C11 1.517(5) . ?
C10 H10A 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.511(5) . ?
C13 C14 1.554(4) . ?
C13 H13A 1.0000 . ?
C14 C15 1.519(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.499(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.534(4) . ?
C17 C23 1.536(5) . ?
C17 H17A 1.0000 . ?
C19 C22 1.517(5) . ?
C19 C20 1.519(5) . ?
C19 C21 1.521(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.515(6) . ?
C23 H23A 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.540(6) . ?
C26 C27 1.545(5) . ?
C26 H26A 1.0000 . ?
C27 C28 1.515(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.375(5) . ?
C28 C33 1.393(5) . ?
C29 C30 1.397(5) . ?
C29 H29A 0.9500 . ?
C30 C31 1.372(5) . ?
C30 H30A 0.9500 . ?
C31 C32 1.370(5) . ?
C31 H31A 0.9500 . ?
C32 C33 1.386(5) . ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
O1W H1WA 0.8421 . ?
O1W H1WB 0.8405 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C26 121.8(2) . . ?
C1 N1 H1N 107.2 . . ?
C26 N1 H1N 124.3 . . ?
C3 N2 C2 122.6(3) . . ?
C3 N2 H2N 119.9 . . ?
C2 N2 H2N 117.3 . . ?
C9 N3 C8 122.5(2) . . ?
C9 N3 H3N 121.4 . . ?
C8 N3 H3N 115.8 . . ?
C12 N4 C10 121.4(3) . . ?
C12 N4 H4N 121.5 . . ?
C10 N4 H4N 117.1 . . ?
C13 N5 C17 120.2(3) . . ?
C13 N5 C16 108.4(2) . . ?
C17 N5 C16 113.6(3) . . ?
C18 N6 C19 127.6(3) . . ?
C18 N6 H6N 108.7 . . ?
C19 N6 H6N 116.2 . . ?
C25 N7 C23 123.2(3) . . ?
C25 N7 H7N 120.5 . . ?
C23 N7 H7N 115.3 . . ?
O1 C1 N1 122.0(3) . . ?
O1 C1 C2 120.1(3) . . ?
N1 C1 C2 117.9(2) . . ?
N2 C2 C1 116.0(3) . . ?
N2 C2 H2A 108.3 . . ?
C1 C2 H2A 108.3 . . ?
N2 C2 H2B 108.3 . . ?
C1 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
O2 C3 N2 122.4(3) . . ?
O2 C3 C8 120.8(3) . . ?
N2 C3 C8 116.8(2) . . ?
C8 C4 C5 114.9(3) . . ?
C8 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
C8 C4 H4B 108.5 . . ?
C5 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
C7 C5 C4 112.2(3) . . ?
C7 C5 C6 110.3(3) . . ?
C4 C5 C6 109.3(3) . . ?
C7 C5 H5A 108.3 . . ?
C4 C5 H5A 108.3 . . ?
C6 C5 H5A 108.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C4 112.1(2) . . ?
N3 C8 C3 111.5(2) . . ?
C4 C8 C3 111.6(2) . . ?
N3 C8 H8A 107.1 . . ?
C4 C8 H8A 107.1 . . ?
C3 C8 H8A 107.1 . . ?
O3 C9 N3 122.8(3) . . ?
O3 C9 C10 119.7(3) . . ?
N3 C9 C10 117.6(3) . . ?
N4 C10 C11 111.0(3) . . ?
N4 C10 C9 113.6(3) . . ?
C11 C10 C9 110.3(3) . . ?
N4 C10 H10A 107.2 . . ?
C11 C10 H10A 107.2 . . ?
C9 C10 H10A 107.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 N4 122.4(3) . . ?
O4 C12 C13 120.5(3) . . ?
N4 C12 C13 117.1(3) . . ?
N5 C13 C12 112.6(2) . . ?
N5 C13 C14 105.0(2) . . ?
C12 C13 C14 110.6(3) . . ?
N5 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C15 C14 C13 102.5(3) . . ?
C15 C14 H14A 111.3 . . ?
C13 C14 H14A 111.3 . . ?
C15 C14 H14B 111.3 . . ?
C13 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
C16 C15 C14 102.2(3) . . ?
C16 C15 H15A 111.3 . . ?
C14 C15 H15A 111.3 . . ?
C16 C15 H15B 111.3 . . ?
C14 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
N5 C16 C15 103.7(3) . . ?
N5 C16 H16A 111.0 . . ?
C15 C16 H16A 111.0 . . ?
N5 C16 H16B 111.0 . . ?
C15 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
N5 C17 C18 109.0(3) . . ?
N5 C17 C23 117.9(3) . . ?
C18 C17 C23 112.0(3) . . ?
N5 C17 H17A 105.7 . . ?
C18 C17 H17A 105.7 . . ?
C23 C17 H17A 105.7 . . ?
O5 C18 N6 124.9(3) . . ?
O5 C18 C17 120.7(3) . . ?
N6 C18 C17 114.4(3) . . ?
N6 C19 C22 109.2(2) . . ?
N6 C19 C20 109.0(2) . . ?
C22 C19 C20 111.7(3) . . ?
N6 C19 C21 106.0(2) . . ?
C22 C19 C21 110.5(3) . . ?
C20 C19 C21 110.3(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N7 C23 C24 110.7(4) . . ?
N7 C23 C17 112.0(3) . . ?
C24 C23 C17 110.4(3) . . ?
N7 C23 H23A 107.9 . . ?
C24 C23 H23A 107.9 . . ?
C17 C23 H23A 107.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O6 C25 N7 124.0(4) . . ?
O6 C25 C26 118.6(3) . . ?
N7 C25 C26 117.4(3) . . ?
N1 C26 C25 113.3(3) . . ?
N1 C26 C27 113.1(3) . . ?
C25 C26 C27 110.8(3) . . ?
N1 C26 H26A 106.3 . . ?
C25 C26 H26A 106.3 . . ?
C27 C26 H26A 106.3 . . ?
C28 C27 C26 114.3(3) . . ?
C28 C27 H27A 108.7 . . ?
C26 C27 H27A 108.7 . . ?
C28 C27 H27B 108.7 . . ?
C26 C27 H27B 108.7 . . ?
H27A C27 H27B 107.6 . . ?
C29 C28 C33 119.3(3) . . ?
C29 C28 C27 121.7(3) . . ?
C33 C28 C27 118.9(3) . . ?
C28 C29 C30 120.7(3) . . ?
C28 C29 H29A 119.7 . . ?
C30 C29 H29A 119.7 . . ?
C31 C30 C29 119.4(3) . . ?
C31 C30 H30A 120.3 . . ?
C29 C30 H30A 120.3 . . ?
C32 C31 C30 120.4(3) . . ?
C32 C31 H31A 119.8 . . ?
C30 C31 H31A 119.8 . . ?
C31 C32 C33 120.6(3) . . ?
C31 C32 H32A 119.7 . . ?
C33 C32 H32A 119.7 . . ?
C32 C33 C28 119.6(3) . . ?
C32 C33 H33A 120.2 . . ?
C28 C33 H33A 120.2 . . ?
H1WA O1W H1WB 122.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N2 0.90 2.39 2.788(3) 107.1 .
N2 H2N O4 0.90 2.01 2.870(3) 158.6 .
N2 H2N N3 0.90 2.32 2.723(3) 106.9 .
N3 H3N O5 0.90 2.05 2.945(3) 170.4 .
N3 H3N N4 0.90 2.45 2.785(3) 102.2 .
N4 H4N N5 0.90 2.30 2.694(4) 106.3 .
N6 H6N O1W 0.90 1.98 2.782(4) 147.9 .
N7 H7N O5 0.90 2.06 2.790(3) 137.3 .
O1W H1WA O3 0.84 1.92 2.760(4) 178.0 1_455

_refine_diff_density_max         0.503
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.039

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.046 0.500 215 74 ' '
_platon_squeeze_details          
;
During the
refinement of the structure, electron density peaks were located
that were believed to be highly disordered
solvent molecules (possibly DMSO/EtOH). Attempts
made to model the solvent molecule were not successful.
The SQUEEZE option in PLATON (Spek, 2003) indicated there was a
large solvent cavity 223 A3. In the final cycles of refinement,
this contribution 74e's to the
electron density was removed from the observed data. The
density, the F(000) value, the molecular weight and the formula are
given without taking into account the results obtained with the
SQUEEZE option PLATON (Spek, 2003). Similar treatments of disordered
solvent molecules were carried out by Stähler et al. (2001),
Cox et al. (2003), Mohamed et al. (2003) and Athimoolam et al. (2005).
References:

Spek, A. L. (2009). Acta Cryst. D65, 148--155.

Athimoolam, S., Kumar, J., Ramakrishnan, V. & Rajaram, R.K. (2005).
Acta Cryst. E61, m2014-m2017.

Cox, J.P., Kumarasammy, Y., Nahar, L., Sarkar D.S. & Shoeb, M.
(2003). Acta Cryst. E59, o975-o977.

Mohamed, A.A., Krause Bauer, A.J., Bruce, E.A. & Bruce M.R.M.
(2003). Acta Cryst. C59, m84-m86.

Stähler, R., Näther, C. & Bensch, W. (2001). Acta Cryst.
C57, 26-27.
;

_shelxl_version_number           2013-3

# start Validation Reply Form
_vrf_PLAT417_d13160_sq_d         
;
PROBLEM: Short Inter D-H..H-D       H1WA   ..  H6N     ..       1.91 Ang. 
RESPONSE: The H atoms on O1W were placed in calculated positions based 
on the formation of idealized hydrogen bonds.
;
_vrf_PLAT420_d13160_sq_d         
;
PROBLEM: D-H Without Acceptor       O1W    -   H1WB   ...          ? Check
RESPONSE: H1WB is most likely involved in an H-bond with the O atom
of the highly disordered partial occupancy EtOH/DMSO solvent. 
;
# end Validation Reply Form


