# 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_1-Form-II-at
_database_code_depnum_ccdc_archive 'CCDC 1436659'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H25 N5 O4'
_chemical_formula_sum            'C33 H25 N5 O4'
_chemical_formula_weight         555.58

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      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                   13.0733(2)
_cell_length_b                   16.7932(3)
_cell_length_c                   19.0162(2)
_cell_angle_alpha                91.0697(11)
_cell_angle_beta                 94.1916(12)
_cell_angle_gamma                103.0744(14)
_cell_volume                     4053.08(11)
_cell_formula_units_Z            6
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    43006
_cell_measurement_theta_min      3.4630
_cell_measurement_theta_max      76.7280

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             1740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.152
_shelx_estimated_absorpt_T_min   0.805
_shelx_estimated_absorpt_T_max   0.895
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
8 -4 -1 0.0746 8.0000 -3.9999 -1.0000 -0.2661 -0.9020 -0.1719
8 -4 2 0.0820 8.0000 -3.9999 2.0000 -0.2672 -0.9427 0.0686
-8 3 4 0.0865 -8.0000 3.0000 4.0000 0.1714 0.8728 0.4103
-1 6 -10 0.1439 -1.0000 6.0000 -9.9999 0.5514 0.1872 -0.7792
-1 1 -12 0.1508 -1.0000 1.0000 -11.9999 0.0845 0.2714 -0.9493
-3 1 12 0.1380 -3.0000 1.0000 12.0000 0.0487 0.1864 0.9952
-3 11 -1 0.0821 -3.0000 10.9999 -0.9999 0.9888 0.2484 -0.0271
-8 4 -3 0.0913 -8.0000 3.9999 -3.0000 0.2675 0.9562 -0.1487
4 8 1 0.1017 4.0000 8.0000 1.0001 0.8017 -0.5855 0.0539
1 0 -12 0.1475 1.0000 -0.0000 -11.9999 0.0179 0.0425 -0.9722
-4 -6 7 0.0863 -4.0000 -6.0000 6.9999 -0.6176 0.4543 0.5912
-3 -4 11 0.1086 -3.0000 -4.0000 10.9999 -0.4185 0.2571 0.9052
-4 10 5 0.0997 -4.0000 9.9999 5.0001 0.8796 0.2987 0.4623
2 -9 7 0.0850 2.0000 -9.0000 6.9999 -0.8174 -0.2324 0.5224
4 -11 -2 0.0756 4.0000 -10.9999 -2.0001 -0.9742 -0.3279 -0.2238
7 -8 0 0.0641 7.0000 -7.9999 -0.0001 -0.6540 -0.7497 -0.0891
-7 8 -2 0.0855 -7.0000 7.9999 -1.9999 0.6547 0.7768 -0.0712
-4 -8 -3 0.0736 -4.0000 -8.0000 -3.0001 -0.8009 0.6126 -0.2142
-7 7 2 0.0851 -7.0000 6.9999 2.0001 0.5597 0.7340 0.2474
7 -7 3 0.0647 7.0000 -6.9999 2.9999 -0.5616 -0.8018 0.1533
-7 -2 -4 0.0891 -7.0000 -2.0000 -4.0000 -0.2798 0.9181 -0.2511
4 8 -2 0.0916 4.0000 8.0000 -1.9999 0.8028 -0.5449 -0.1865
0 10 3 0.1002 -0.0000 10.0000 3.0001 0.9342 -0.1549 0.2601
0 10 -2 0.0842 -0.0000 10.0000 -1.9999 0.9360 -0.0871 -0.1407
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
__diffrn_source                  'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_reflns_number            84317
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.482
_diffrn_reflns_theta_max         77.022
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             17003
_reflns_number_gt                15211
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+2.6226P] 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         17003
_refine_ls_number_parameters     1171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
O101 O 0.96670(8) 0.48710(7) 0.58585(6) 0.0253(2) Uani 1 1 d . . . . .
O102 O 0.87714(9) 0.26084(7) 0.32610(6) 0.0288(2) Uani 1 1 d . . . . .
O103 O 0.37368(8) 0.24116(7) 0.44198(6) 0.0270(2) Uani 1 1 d . . . . .
O104 O 0.71178(8) 0.20757(6) 0.57098(6) 0.0223(2) Uani 1 1 d . . . . .
N101 N 0.87395(10) 0.35678(8) 0.56243(7) 0.0223(3) Uani 1 1 d . . . . .
H11N H 0.8125(16) 0.3231(12) 0.5620(10) 0.027 Uiso 1 1 d . U . . .
N102 N 0.83960(10) 0.26013(8) 0.44196(7) 0.0227(3) Uani 1 1 d . . . . .
H12N H 0.7853(16) 0.2576(12) 0.4670(10) 0.027 Uiso 1 1 d . U . . .
N103 N 0.51182(10) 0.21099(8) 0.50953(7) 0.0212(3) Uani 1 1 d . . . . .
H13N H 0.5754(16) 0.2102(12) 0.5075(10) 0.025 Uiso 1 1 d . U . . .
N104 N 0.58742(10) 0.10084(8) 0.60450(7) 0.0200(2) Uani 1 1 d . . . . .
H14N H 0.5757(15) 0.0497(12) 0.6171(10) 0.024 Uiso 1 1 d . U . . .
N105 N 0.63776(10) 0.24893(7) 0.40568(6) 0.0186(2) Uani 1 1 d . . . . .
C101 C 0.68280(13) 0.40916(10) 0.58450(9) 0.0293(3) Uani 1 1 d . . . . .
H10A H 0.6793 0.3524 0.5894 0.035 Uiso 1 1 calc R U . . .
C102 C 0.59134(14) 0.43820(11) 0.58194(11) 0.0351(4) Uani 1 1 d . . . . .
H102 H 0.5252 0.4012 0.5852 0.042 Uiso 1 1 calc R U . . .
C103 C 0.59597(14) 0.52098(11) 0.57466(9) 0.0306(4) Uani 1 1 d . . . . .
H10B H 0.5331 0.5405 0.5724 0.037 Uiso 1 1 calc R U . . .
C104 C 0.69222(13) 0.57492(10) 0.57069(9) 0.0278(3) Uani 1 1 d . . . . .
H10C H 0.6956 0.6317 0.5662 0.033 Uiso 1 1 calc R U . . .
C105 C 0.78383(13) 0.54620(10) 0.57329(8) 0.0247(3) Uani 1 1 d . . . . .
H105 H 0.8498 0.5835 0.5705 0.030 Uiso 1 1 calc R U . . .
C106 C 0.77984(12) 0.46342(9) 0.57989(7) 0.0204(3) Uani 1 1 d . . . . .
C107 C 0.88199(11) 0.43727(9) 0.57779(7) 0.0193(3) Uani 1 1 d . . . . .
C108 C 0.95754(11) 0.32324(9) 0.54095(8) 0.0200(3) Uani 1 1 d . . . . .
C109 C 1.05428(12) 0.33746(9) 0.58001(9) 0.0253(3) Uani 1 1 d . . . . .
H109 H 1.0654 0.3691 0.6230 0.030 Uiso 1 1 calc R U . . .
C110 C 1.13465(13) 0.30523(10) 0.55601(10) 0.0288(3) Uani 1 1 d . . . . .
H110 H 1.2009 0.3150 0.5826 0.035 Uiso 1 1 calc R U . . .
C111 C 1.11891(12) 0.25880(10) 0.49341(10) 0.0285(3) Uani 1 1 d . . . . .
H111 H 1.1746 0.2374 0.4772 0.034 Uiso 1 1 calc R U . . .
C112 C 1.02203(12) 0.24354(9) 0.45437(9) 0.0258(3) Uani 1 1 d . . . . .
H112 H 1.0114 0.2116 0.4116 0.031 Uiso 1 1 calc R U . . .
C113 C 0.94058(11) 0.27510(9) 0.47813(8) 0.0198(3) Uani 1 1 d . . . . .
C114 C 0.81540(12) 0.25980(8) 0.37128(8) 0.0200(3) Uani 1 1 d . . . . .
C115 C 0.70169(12) 0.26134(8) 0.35309(8) 0.0191(3) Uani 1 1 d . . . . .
C116 C 0.66889(12) 0.27951(9) 0.28501(8) 0.0232(3) Uani 1 1 d . . . . .
H116 H 0.7157 0.2861 0.2485 0.028 Uiso 1 1 calc R U . . .
C117 C 0.56608(13) 0.28768(10) 0.27213(8) 0.0259(3) Uani 1 1 d . . . . .
H117 H 0.5416 0.3015 0.2267 0.031 Uiso 1 1 calc R U . . .
C118 C 0.49915(12) 0.27542(9) 0.32649(8) 0.0231(3) Uani 1 1 d . . . . .
H118 H 0.4287 0.2814 0.3192 0.028 Uiso 1 1 calc R U . . .
C119 C 0.53786(11) 0.25418(8) 0.39161(8) 0.0191(3) Uani 1 1 d . . . . .
C120 C 0.46549(11) 0.23546(9) 0.45027(8) 0.0199(3) Uani 1 1 d . . . . .
C121 C 0.46840(12) 0.19427(9) 0.57466(8) 0.0208(3) Uani 1 1 d . . . . .
C122 C 0.38563(12) 0.22784(10) 0.59443(9) 0.0261(3) Uani 1 1 d . . . . .
H122 H 0.3580 0.2630 0.5635 0.031 Uiso 1 1 calc R U . . .
C123 C 0.34339(13) 0.21032(11) 0.65889(9) 0.0295(3) Uani 1 1 d . . . . .
H123 H 0.2857 0.2321 0.6710 0.035 Uiso 1 1 calc R U . . .
C124 C 0.38478(13) 0.16127(10) 0.70568(8) 0.0265(3) Uani 1 1 d . . . . .
H124 H 0.3564 0.1500 0.7500 0.032 Uiso 1 1 calc R U . . .
C125 C 0.46805(12) 0.12883(9) 0.68707(8) 0.0219(3) Uani 1 1 d . . . . .
H125 H 0.4976 0.0962 0.7194 0.026 Uiso 1 1 calc R U . . .
C126 C 0.50897(11) 0.14350(8) 0.62157(8) 0.0190(3) Uani 1 1 d . . . . .
C127 C 0.68329(11) 0.13392(9) 0.58289(7) 0.0184(3) Uani 1 1 d . . . . .
C128 C 0.75435(12) 0.07635(9) 0.57449(7) 0.0192(3) Uani 1 1 d . . . . .
C129 C 0.86259(12) 0.10884(9) 0.58034(8) 0.0217(3) Uani 1 1 d . . . . .
H129 H 0.8891 0.1661 0.5884 0.026 Uiso 1 1 calc R U . . .
C130 C 0.93204(12) 0.05799(10) 0.57444(8) 0.0251(3) Uani 1 1 d . . . . .
H130 H 1.0059 0.0803 0.5790 0.030 Uiso 1 1 calc R U . . .
C131 C 0.89356(13) -0.02529(10) 0.56190(8) 0.0267(3) Uani 1 1 d . . . . .
H131 H 0.9412 -0.0600 0.5580 0.032 Uiso 1 1 calc R U . . .
C132 C 0.78566(13) -0.05826(10) 0.55494(9) 0.0276(3) Uani 1 1 d . . . . .
H132 H 0.7596 -0.1153 0.5457 0.033 Uiso 1 1 calc R U . . .
C133 C 0.71599(12) -0.00776(9) 0.56154(8) 0.0236(3) Uani 1 1 d . . . . .
H133 H 0.6422 -0.0303 0.5572 0.028 Uiso 1 1 calc R U . . .
O201 O 0.08755(9) 0.62440(6) 0.25419(6) 0.0258(2) Uani 1 1 d . . . . .
O202 O 0.20093(9) 0.61360(7) 0.00695(6) 0.0244(2) Uani 1 1 d . . . . .
O203 O -0.30859(8) 0.57669(7) 0.11631(6) 0.0279(2) Uani 1 1 d . . . . .
O204 O -0.13997(8) 0.36891(6) 0.18466(5) 0.0222(2) Uani 1 1 d . . . . .
N201 N 0.22626(10) 0.72154(8) 0.22520(7) 0.0221(3) Uani 1 1 d . . . . .
H21N H 0.2517(15) 0.7737(12) 0.2131(10) 0.026 Uiso 1 1 d . U . . .
N202 N 0.15845(10) 0.59528(8) 0.12063(7) 0.0201(2) Uani 1 1 d . . . . .
H22N H 0.1066(15) 0.5888(11) 0.1482(10) 0.024 Uiso 1 1 d . U . . .
N203 N -0.18043(10) 0.53069(8) 0.18134(7) 0.0211(3) Uani 1 1 d . . . . .
H23N H -0.1196(16) 0.5220(12) 0.1772(10) 0.025 Uiso 1 1 d . U . . .
N204 N -0.07567(9) 0.45104(7) 0.28219(6) 0.0175(2) Uani 1 1 d . . . . .
H24N H -0.0255(15) 0.4621(11) 0.3169(10) 0.021 Uiso 1 1 d . U . . .
N205 N -0.04525(9) 0.57982(7) 0.08251(6) 0.0173(2) Uani 1 1 d . . . . .
C201 C -0.04805(13) 0.72923(10) 0.23629(9) 0.0276(3) Uani 1 1 d . . . . .
H20A H -0.0764 0.6718 0.2346 0.033 Uiso 1 1 calc R U . . .
C202 C -0.11516(14) 0.78218(12) 0.23089(10) 0.0344(4) Uani 1 1 d . . . . .
H202 H -0.1891 0.7612 0.2239 0.041 Uiso 1 1 calc R U . . .
C203 C -0.07434(15) 0.86584(11) 0.23572(9) 0.0338(4) Uani 1 1 d . . . . .
H203 H -0.1204 0.9022 0.2326 0.041 Uiso 1 1 calc R U . . .
C204 C 0.03324(15) 0.89648(10) 0.24506(9) 0.0308(4) Uani 1 1 d . . . . .
H20B H 0.0608 0.9539 0.2492 0.037 Uiso 1 1 calc R U . . .
C205 C 0.10170(13) 0.84364(10) 0.24844(8) 0.0255(3) Uani 1 1 d . . . . .
H205 H 0.1757 0.8649 0.2536 0.031 Uiso 1 1 calc R U . . .
C206 C 0.06066(12) 0.75935(9) 0.24420(7) 0.0218(3) Uani 1 1 d . . . . .
C207 C 0.12631(12) 0.69666(9) 0.24297(7) 0.0209(3) Uani 1 1 d . . . . .
C208 C 0.29137(11) 0.66652(9) 0.20988(8) 0.0200(3) Uani 1 1 d . . . . .
C209 C 0.38963(12) 0.67638(9) 0.24632(8) 0.0242(3) Uani 1 1 d . . . . .
H209 H 0.4089 0.7142 0.2854 0.029 Uiso 1 1 calc R U . . .
C210 C 0.45977(12) 0.63113(10) 0.22578(9) 0.0271(3) Uani 1 1 d . . . . .
H210 H 0.5270 0.6381 0.2508 0.033 Uiso 1 1 calc R U . . .
C211 C 0.43179(13) 0.57582(10) 0.16886(9) 0.0280(3) Uani 1 1 d . . . . .
H211 H 0.4807 0.5462 0.1540 0.034 Uiso 1 1 calc R U . . .
C212 C 0.33242(12) 0.56364(10) 0.13352(9) 0.0254(3) Uani 1 1 d . . . . .
H212 H 0.3130 0.5250 0.0950 0.030 Uiso 1 1 calc R U . . .
C213 C 0.26136(11) 0.60801(9) 0.15443(8) 0.0199(3) Uani 1 1 d . . . . .
C214 C 0.13540(11) 0.60127(8) 0.05102(8) 0.0187(3) Uani 1 1 d . . . . .
C215 C 0.02050(11) 0.59663(8) 0.03103(7) 0.0180(3) Uani 1 1 d . . . . .
C216 C -0.01112(12) 0.61360(9) -0.03725(8) 0.0219(3) Uani 1 1 d . . . . .
H216 H 0.0376 0.6236 -0.0725 0.026 Uiso 1 1 calc R U . . .
C217 C -0.11589(13) 0.61554(10) -0.05244(8) 0.0250(3) Uani 1 1 d . . . . .
H217 H -0.1404 0.6268 -0.0986 0.030 Uiso 1 1 calc R U . . .
C218 C -0.18447(12) 0.60087(9) 0.00050(8) 0.0225(3) Uani 1 1 d . . . . .
H218 H -0.2560 0.6038 -0.0081 0.027 Uiso 1 1 calc R U . . .
C219 C -0.14568(11) 0.58178(8) 0.06675(7) 0.0179(3) Uani 1 1 d . . . . .
C220 C -0.22049(11) 0.56296(8) 0.12406(8) 0.0189(3) Uani 1 1 d . . . . .
C221 C -0.22540(11) 0.51105(9) 0.24539(8) 0.0199(3) Uani 1 1 d . . . . .
C222 C -0.31910(13) 0.53145(11) 0.26183(9) 0.0274(3) Uani 1 1 d . . . . .
H222 H -0.3581 0.5553 0.2274 0.033 Uiso 1 1 calc R U . . .
C223 C -0.35521(13) 0.51695(11) 0.32832(9) 0.0287(3) Uani 1 1 d . . . . .
H223 H -0.4193 0.5304 0.3388 0.034 Uiso 1 1 calc R U . . .
C224 C -0.29870(12) 0.48301(10) 0.37967(8) 0.0242(3) Uani 1 1 d . . . . .
H224 H -0.3227 0.4748 0.4255 0.029 Uiso 1 1 calc R U . . .
C225 C -0.20696(11) 0.46125(9) 0.36323(8) 0.0196(3) Uani 1 1 d . . . . .
H225 H -0.1682 0.4378 0.3981 0.024 Uiso 1 1 calc R U . . .
C226 C -0.17077(11) 0.47337(8) 0.29621(7) 0.0171(3) Uani 1 1 d . . . . .
C227 C -0.06797(11) 0.39675(8) 0.22976(7) 0.0175(3) Uani 1 1 d . . . . .
C228 C 0.03623(12) 0.37403(9) 0.23006(7) 0.0195(3) Uani 1 1 d . . . . .
C229 C 0.03589(13) 0.29440(10) 0.20802(8) 0.0251(3) Uani 1 1 d . . . . .
H229 H -0.0288 0.2572 0.1934 0.030 Uiso 1 1 calc R U . . .
C230 C 0.12976(15) 0.26946(11) 0.20742(9) 0.0320(4) Uani 1 1 d . . . . .
H230 H 0.1294 0.2149 0.1930 0.038 Uiso 1 1 calc R U . . .
C231 C 0.22451(14) 0.32401(12) 0.22790(9) 0.0321(4) Uani 1 1 d . . . . .
H231 H 0.2888 0.3066 0.2279 0.039 Uiso 1 1 calc R U . . .
C232 C 0.22538(13) 0.40405(12) 0.24846(8) 0.0300(4) Uani 1 1 d . . . . .
H232 H 0.2904 0.4417 0.2615 0.036 Uiso 1 1 calc R U . . .
C233 C 0.13088(12) 0.42919(10) 0.24999(8) 0.0231(3) Uani 1 1 d . . . . .
H233 H 0.1312 0.4837 0.2646 0.028 Uiso 1 1 calc R U . . .
O301 O 0.36772(9) -0.14611(7) 0.15291(7) 0.0317(3) Uani 1 1 d . . . . .
O302 O 0.49523(9) 0.06086(6) 0.35387(6) 0.0244(2) Uani 1 1 d . . . . .
O303 O 0.96951(9) 0.07895(7) 0.19731(6) 0.0271(2) Uani 1 1 d . . . . .
O304 O 0.61966(8) 0.11759(6) 0.09154(6) 0.0222(2) Uani 1 1 d . . . . .
N301 N 0.44093(10) -0.02254(8) 0.11212(7) 0.0217(3) Uani 1 1 d . . . . .
H31N H 0.4936(16) 0.0094(12) 0.0941(10) 0.026 Uiso 1 1 d . U . . .
N302 N 0.51146(10) 0.06975(8) 0.23509(7) 0.0214(3) Uani 1 1 d . . . . .
H32N H 0.5614(15) 0.0755(12) 0.2024(10) 0.026 Uiso 1 1 d . U . . .
N303 N 0.82426(10) 0.11103(8) 0.13945(7) 0.0197(2) Uani 1 1 d . . . . .
H33N H 0.7605(16) 0.1132(11) 0.1449(10) 0.024 Uiso 1 1 d . U . . .
N304 N 0.73811(10) 0.22244(7) 0.04894(6) 0.0182(2) Uani 1 1 d . . . . .
H34N H 0.7489(14) 0.2717(12) 0.0352(10) 0.022 Uiso 1 1 d . U . . .
N305 N 0.71715(9) 0.07756(7) 0.25368(6) 0.0179(2) Uani 1 1 d . . . . .
C301 C 0.52254(14) -0.21800(10) 0.10083(8) 0.0278(3) Uani 1 1 d . . . . .
H30A H 0.4577 -0.2535 0.1101 0.033 Uiso 1 1 calc R U . . .
C302 C 0.60817(16) -0.25036(11) 0.08749(9) 0.0340(4) Uani 1 1 d . . . . .
H302 H 0.6018 -0.3078 0.0875 0.041 Uiso 1 1 calc R U . . .
C303 C 0.70274(16) -0.19894(12) 0.07418(10) 0.0380(4) Uani 1 1 d . . . . .
H30B H 0.7618 -0.2210 0.0659 0.046 Uiso 1 1 calc R U . . .
C304 C 0.71156(15) -0.11541(12) 0.07284(12) 0.0430(5) Uani 1 1 d . . . . .
H30C H 0.7764 -0.0803 0.0630 0.052 Uiso 1 1 calc R U . . .
C305 C 0.62584(14) -0.08254(11) 0.08589(11) 0.0349(4) Uani 1 1 d . . . . .
H305 H 0.6321 -0.0251 0.0846 0.042 Uiso 1 1 calc R U . . .
C306 C 0.53084(12) -0.13380(9) 0.10081(8) 0.0233(3) Uani 1 1 d . . . . .
C307 C 0.43932(12) -0.10240(9) 0.12325(8) 0.0219(3) Uani 1 1 d . . . . .
C308 C 0.37028(12) 0.01626(9) 0.14619(8) 0.0214(3) Uani 1 1 d . . . . .
C309 C 0.26766(12) 0.00858(10) 0.11761(9) 0.0282(3) Uani 1 1 d . . . . .
H309 H 0.2448 -0.0197 0.0735 0.034 Uiso 1 1 calc R U . . .
C310 C 0.19835(13) 0.04264(11) 0.15406(10) 0.0336(4) Uani 1 1 d . . . . .
H310 H 0.1282 0.0381 0.1344 0.040 Uiso 1 1 calc R U . . .
C311 C 0.23104(13) 0.08289(10) 0.21858(10) 0.0308(4) Uani 1 1 d . . . . .
H311 H 0.1824 0.1043 0.2437 0.037 Uiso 1 1 calc R U . . .
C312 C 0.33416(12) 0.09251(9) 0.24721(9) 0.0257(3) Uani 1 1 d . . . . .
H312 H 0.3565 0.1209 0.2913 0.031 Uiso 1 1 calc R U . . .
C313 C 0.40445(11) 0.05980(9) 0.21026(8) 0.0210(3) Uani 1 1 d . . . . .
C314 C 0.54880(12) 0.06705(8) 0.30263(8) 0.0201(3) Uani 1 1 d . . . . .
C315 C 0.66423(12) 0.06777(8) 0.31166(8) 0.0191(3) Uani 1 1 d . . . . .
C316 C 0.70922(13) 0.05483(9) 0.37766(8) 0.0240(3) Uani 1 1 d . . . . .
H316 H 0.6691 0.0492 0.4177 0.029 Uiso 1 1 calc R U . . .
C317 C 0.81393(13) 0.05033(10) 0.38361(8) 0.0268(3) Uani 1 1 d . . . . .
H317 H 0.8469 0.0408 0.4279 0.032 Uiso 1 1 calc R U . . .
C318 C 0.86991(12) 0.05993(9) 0.32413(8) 0.0234(3) Uani 1 1 d . . . . .
H318 H 0.9417 0.0567 0.3266 0.028 Uiso 1 1 calc R U . . .
C319 C 0.81848(11) 0.07447(8) 0.26055(8) 0.0187(3) Uani 1 1 d . . . . .
C320 C 0.87915(11) 0.08780(9) 0.19573(8) 0.0196(3) Uani 1 1 d . . . . .
C321 C 0.85965(11) 0.12852(9) 0.07193(8) 0.0191(3) Uani 1 1 d . . . . .
C322 C 0.93995(12) 0.09528(10) 0.04731(8) 0.0243(3) Uani 1 1 d . . . . .
H322 H 0.9683 0.0581 0.0754 0.029 Uiso 1 1 calc R U . . .
C323 C 0.97867(13) 0.11590(10) -0.01751(9) 0.0269(3) Uani 1 1 d . . . . .
H323 H 1.0348 0.0943 -0.0327 0.032 Uiso 1 1 calc R U . . .
C324 C 0.93562(13) 0.16806(10) -0.06018(8) 0.0252(3) Uani 1 1 d . . . . .
H324 H 0.9626 0.1828 -0.1043 0.030 Uiso 1 1 calc R U . . .
C325 C 0.85312(12) 0.19833(9) -0.03775(8) 0.0213(3) Uani 1 1 d . . . . .
H325 H 0.8215 0.2320 -0.0679 0.026 Uiso 1 1 calc R U . . .
C326 C 0.81533(11) 0.18051(8) 0.02833(7) 0.0182(3) Uani 1 1 d . . . . .
C327 C 0.64597(11) 0.19069(9) 0.07576(7) 0.0174(3) Uani 1 1 d . . . . .
C328 C 0.57558(11) 0.24816(9) 0.08584(7) 0.0179(3) Uani 1 1 d . . . . .
C329 C 0.46810(12) 0.21471(9) 0.08735(8) 0.0211(3) Uani 1 1 d . . . . .
H329 H 0.4421 0.1572 0.0819 0.025 Uiso 1 1 calc R U . . .
C330 C 0.39876(12) 0.26480(10) 0.09681(8) 0.0247(3) Uani 1 1 d . . . . .
H330 H 0.3256 0.2416 0.0983 0.030 Uiso 1 1 calc R U . . .
C331 C 0.43672(12) 0.34907(10) 0.10402(8) 0.0247(3) Uani 1 1 d . . . . .
H331 H 0.3894 0.3835 0.1103 0.030 Uiso 1 1 calc R U . . .
C332 C 0.54377(13) 0.38306(10) 0.10210(8) 0.0248(3) Uani 1 1 d . . . . .
H332 H 0.5693 0.4407 0.1067 0.030 Uiso 1 1 calc R U . . .
C333 C 0.61352(12) 0.33302(9) 0.09354(8) 0.0209(3) Uani 1 1 d . . . . .
H333 H 0.6868 0.3563 0.0929 0.025 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
O101 C107 1.2252(18) . ?
O102 C114 1.2187(18) . ?
O103 C120 1.2246(18) . ?
O104 C127 1.2387(18) . ?
N101 C107 1.3564(19) . ?
N101 C108 1.4190(19) . ?
N101 H11N 0.87(2) . ?
N102 C114 1.358(2) . ?
N102 C113 1.4106(19) . ?
N102 H12N 0.88(2) . ?
N103 C120 1.3549(19) . ?
N103 C121 1.4066(19) . ?
N103 H13N 0.84(2) . ?
N104 C127 1.3480(19) . ?
N104 C126 1.4293(18) . ?
N104 H14N 0.88(2) . ?
N105 C119 1.3368(19) . ?
N105 C115 1.3391(19) . ?
C101 C102 1.388(2) . ?
C101 C106 1.394(2) . ?
C101 H10A 0.9500 . ?
C102 C103 1.388(2) . ?
C102 H102 0.9500 . ?
C103 C104 1.382(2) . ?
C103 H10B 0.9500 . ?
C104 C105 1.387(2) . ?
C104 H10C 0.9500 . ?
C105 C106 1.388(2) . ?
C105 H105 0.9500 . ?
C106 C107 1.500(2) . ?
C108 C109 1.388(2) . ?
C108 C113 1.405(2) . ?
C109 C110 1.387(2) . ?
C109 H109 0.9500 . ?
C110 C111 1.387(3) . ?
C110 H110 0.9500 . ?
C111 C112 1.389(2) . ?
C111 H111 0.9500 . ?
C112 C113 1.391(2) . ?
C112 H112 0.9500 . ?
C114 C115 1.508(2) . ?
C115 C116 1.395(2) . ?
C116 C117 1.386(2) . ?
C116 H116 0.9500 . ?
C117 C118 1.391(2) . ?
C117 H117 0.9500 . ?
C118 C119 1.387(2) . ?
C118 H118 0.9500 . ?
C119 C120 1.507(2) . ?
C121 C122 1.399(2) . ?
C121 C126 1.403(2) . ?
C122 C123 1.390(2) . ?
C122 H122 0.9500 . ?
C123 C124 1.386(2) . ?
C123 H123 0.9500 . ?
C124 C125 1.387(2) . ?
C124 H124 0.9500 . ?
C125 C126 1.396(2) . ?
C125 H125 0.9500 . ?
C127 C128 1.4986(19) . ?
C128 C129 1.392(2) . ?
C128 C133 1.398(2) . ?
C129 C130 1.389(2) . ?
C129 H129 0.9500 . ?
C130 C131 1.385(2) . ?
C130 H130 0.9500 . ?
C131 C132 1.389(2) . ?
C131 H131 0.9500 . ?
C132 C133 1.388(2) . ?
C132 H132 0.9500 . ?
C133 H133 0.9500 . ?
O201 C207 1.2337(18) . ?
O202 C214 1.2291(18) . ?
O203 C220 1.2239(18) . ?
O204 C227 1.2280(18) . ?
N201 C207 1.349(2) . ?
N201 C208 1.4301(19) . ?
N201 H21N 0.90(2) . ?
N202 C214 1.3467(19) . ?
N202 C213 1.4167(19) . ?
N202 H22N 0.88(2) . ?
N203 C220 1.3497(19) . ?
N203 C221 1.4034(18) . ?
N203 H23N 0.85(2) . ?
N204 C227 1.3630(18) . ?
N204 C226 1.4187(18) . ?
N204 H24N 0.882(19) . ?
N205 C219 1.3330(19) . ?
N205 C215 1.3417(18) . ?
C201 C202 1.383(2) . ?
C201 C206 1.392(2) . ?
C201 H20A 0.9500 . ?
C202 C203 1.384(3) . ?
C202 H202 0.9500 . ?
C203 C204 1.381(3) . ?
C203 H203 0.9500 . ?
C204 C205 1.395(2) . ?
C204 H20B 0.9500 . ?
C205 C206 1.394(2) . ?
C205 H205 0.9500 . ?
C206 C207 1.502(2) . ?
C208 C209 1.388(2) . ?
C208 C213 1.399(2) . ?
C209 C210 1.388(2) . ?
C209 H209 0.9500 . ?
C210 C211 1.385(2) . ?
C210 H210 0.9500 . ?
C211 C212 1.389(2) . ?
C211 H211 0.9500 . ?
C212 C213 1.390(2) . ?
C212 H212 0.9500 . ?
C214 C215 1.506(2) . ?
C215 C216 1.388(2) . ?
C216 C217 1.387(2) . ?
C216 H216 0.9500 . ?
C217 C218 1.385(2) . ?
C217 H217 0.9500 . ?
C218 C219 1.394(2) . ?
C218 H218 0.9500 . ?
C219 C220 1.5076(19) . ?
C221 C222 1.399(2) . ?
C221 C226 1.404(2) . ?
C222 C223 1.388(2) . ?
C222 H222 0.9500 . ?
C223 C224 1.389(2) . ?
C223 H223 0.9500 . ?
C224 C225 1.385(2) . ?
C224 H224 0.9500 . ?
C225 C226 1.394(2) . ?
C225 H225 0.9500 . ?
C227 C228 1.4951(19) . ?
C228 C233 1.390(2) . ?
C228 C229 1.393(2) . ?
C229 C230 1.384(2) . ?
C229 H229 0.9500 . ?
C230 C231 1.388(3) . ?
C230 H230 0.9500 . ?
C231 C232 1.390(3) . ?
C231 H231 0.9500 . ?
C232 C233 1.395(2) . ?
C232 H232 0.9500 . ?
C233 H233 0.9500 . ?
O301 C307 1.2307(19) . ?
O302 C314 1.2334(18) . ?
O303 C320 1.2219(18) . ?
O304 C327 1.2462(17) . ?
N301 C307 1.3572(19) . ?
N301 C308 1.4290(19) . ?
N301 H31N 0.87(2) . ?
N302 C314 1.346(2) . ?
N302 C313 1.4152(19) . ?
N302 H32N 0.92(2) . ?
N303 C320 1.3574(19) . ?
N303 C321 1.4101(18) . ?
N303 H33N 0.86(2) . ?
N304 C327 1.3434(18) . ?
N304 C326 1.4275(18) . ?
N304 H34N 0.856(19) . ?
N305 C319 1.3344(19) . ?
N305 C315 1.3373(18) . ?
C301 C302 1.387(2) . ?
C301 C306 1.394(2) . ?
C301 H30A 0.9500 . ?
C302 C303 1.382(3) . ?
C302 H302 0.9500 . ?
C303 C304 1.382(3) . ?
C303 H30B 0.9500 . ?
C304 C305 1.392(2) . ?
C304 H30C 0.9500 . ?
C305 C306 1.393(2) . ?
C305 H305 0.9500 . ?
C306 C307 1.498(2) . ?
C308 C309 1.387(2) . ?
C308 C313 1.399(2) . ?
C309 C310 1.393(2) . ?
C309 H309 0.9500 . ?
C310 C311 1.381(3) . ?
C310 H310 0.9500 . ?
C311 C312 1.390(2) . ?
C311 H311 0.9500 . ?
C312 C313 1.396(2) . ?
C312 H312 0.9500 . ?
C314 C315 1.504(2) . ?
C315 C316 1.389(2) . ?
C316 C317 1.385(2) . ?
C316 H316 0.9500 . ?
C317 C318 1.384(2) . ?
C317 H317 0.9500 . ?
C318 C319 1.393(2) . ?
C318 H318 0.9500 . ?
C319 C320 1.507(2) . ?
C321 C322 1.400(2) . ?
C321 C326 1.404(2) . ?
C322 C323 1.387(2) . ?
C322 H322 0.9500 . ?
C323 C324 1.388(2) . ?
C323 H323 0.9500 . ?
C324 C325 1.382(2) . ?
C324 H324 0.9500 . ?
C325 C326 1.397(2) . ?
C325 H325 0.9500 . ?
C327 C328 1.4951(19) . ?
C328 C329 1.393(2) . ?
C328 C333 1.400(2) . ?
C329 C330 1.387(2) . ?
C329 H329 0.9500 . ?
C330 C331 1.390(2) . ?
C330 H330 0.9500 . ?
C331 C332 1.390(2) . ?
C331 H331 0.9500 . ?
C332 C333 1.388(2) . ?
C332 H332 0.9500 . ?
C333 H333 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C107 N101 C108 124.62(13) . . ?
C107 N101 H11N 119.0(13) . . ?
C108 N101 H11N 116.2(13) . . ?
C114 N102 C113 127.73(13) . . ?
C114 N102 H12N 113.7(13) . . ?
C113 N102 H12N 117.9(13) . . ?
C120 N103 C121 127.50(13) . . ?
C120 N103 H13N 114.9(13) . . ?
C121 N103 H13N 117.4(13) . . ?
C127 N104 C126 126.78(12) . . ?
C127 N104 H14N 117.2(12) . . ?
C126 N104 H14N 115.0(12) . . ?
C119 N105 C115 117.88(13) . . ?
C102 C101 C106 119.86(15) . . ?
C102 C101 H10A 120.1 . . ?
C106 C101 H10A 120.1 . . ?
C103 C102 C101 120.32(16) . . ?
C103 C102 H102 119.8 . . ?
C101 C102 H102 119.8 . . ?
C104 C103 C102 119.87(15) . . ?
C104 C103 H10B 120.1 . . ?
C102 C103 H10B 120.1 . . ?
C103 C104 C105 120.02(15) . . ?
C103 C104 H10C 120.0 . . ?
C105 C104 H10C 120.0 . . ?
C104 C105 C106 120.50(15) . . ?
C104 C105 H105 119.7 . . ?
C106 C105 H105 119.7 . . ?
C105 C106 C101 119.43(14) . . ?
C105 C106 C107 116.79(13) . . ?
C101 C106 C107 123.71(14) . . ?
O101 C107 N101 122.81(14) . . ?
O101 C107 C106 121.22(13) . . ?
N101 C107 C106 115.86(13) . . ?
C109 C108 C113 120.11(14) . . ?
C109 C108 N101 121.66(14) . . ?
C113 C108 N101 118.22(13) . . ?
C110 C109 C108 119.68(15) . . ?
C110 C109 H109 120.2 . . ?
C108 C109 H109 120.2 . . ?
C109 C110 C111 120.45(15) . . ?
C109 C110 H110 119.8 . . ?
C111 C110 H110 119.8 . . ?
C110 C111 C112 120.26(15) . . ?
C110 C111 H111 119.9 . . ?
C112 C111 H111 119.9 . . ?
C111 C112 C113 119.82(15) . . ?
C111 C112 H112 120.1 . . ?
C113 C112 H112 120.1 . . ?
C112 C113 C108 119.66(14) . . ?
C112 C113 N102 122.64(14) . . ?
C108 C113 N102 117.70(13) . . ?
O102 C114 N102 125.52(14) . . ?
O102 C114 C115 121.99(14) . . ?
N102 C114 C115 112.45(12) . . ?
N105 C115 C116 123.13(14) . . ?
N105 C115 C114 116.84(13) . . ?
C116 C115 C114 119.94(13) . . ?
C117 C116 C115 118.11(14) . . ?
C117 C116 H116 120.9 . . ?
C115 C116 H116 120.9 . . ?
C116 C117 C118 119.22(14) . . ?
C116 C117 H117 120.4 . . ?
C118 C117 H117 120.4 . . ?
C119 C118 C117 118.36(14) . . ?
C119 C118 H118 120.8 . . ?
C117 C118 H118 120.8 . . ?
N105 C119 C118 123.19(14) . . ?
N105 C119 C120 117.17(13) . . ?
C118 C119 C120 119.64(13) . . ?
O103 C120 N103 125.61(14) . . ?
O103 C120 C119 120.94(13) . . ?
N103 C120 C119 113.43(13) . . ?
C122 C121 C126 118.72(14) . . ?
C122 C121 N103 121.48(14) . . ?
C126 C121 N103 119.80(13) . . ?
C123 C122 C121 120.66(15) . . ?
C123 C122 H122 119.7 . . ?
C121 C122 H122 119.7 . . ?
C124 C123 C122 120.52(15) . . ?
C124 C123 H123 119.7 . . ?
C122 C123 H123 119.7 . . ?
C123 C124 C125 119.23(14) . . ?
C123 C124 H124 120.4 . . ?
C125 C124 H124 120.4 . . ?
C124 C125 C126 120.97(14) . . ?
C124 C125 H125 119.5 . . ?
C126 C125 H125 119.5 . . ?
C125 C126 C121 119.85(13) . . ?
C125 C126 N104 116.73(13) . . ?
C121 C126 N104 123.32(13) . . ?
O104 C127 N104 122.34(13) . . ?
O104 C127 C128 121.60(13) . . ?
N104 C127 C128 116.05(12) . . ?
C129 C128 C133 119.51(14) . . ?
C129 C128 C127 117.91(13) . . ?
C133 C128 C127 122.58(13) . . ?
C130 C129 C128 120.28(14) . . ?
C130 C129 H129 119.9 . . ?
C128 C129 H129 119.9 . . ?
C131 C130 C129 119.93(15) . . ?
C131 C130 H130 120.0 . . ?
C129 C130 H130 120.0 . . ?
C130 C131 C132 120.30(14) . . ?
C130 C131 H131 119.9 . . ?
C132 C131 H131 119.9 . . ?
C133 C132 C131 119.95(15) . . ?
C133 C132 H132 120.0 . . ?
C131 C132 H132 120.0 . . ?
C132 C133 C128 120.03(15) . . ?
C132 C133 H133 120.0 . . ?
C128 C133 H133 120.0 . . ?
C207 N201 C208 123.43(13) . . ?
C207 N201 H21N 120.8(12) . . ?
C208 N201 H21N 114.5(12) . . ?
C214 N202 C213 125.29(13) . . ?
C214 N202 H22N 117.8(12) . . ?
C213 N202 H22N 116.5(12) . . ?
C220 N203 C221 128.68(13) . . ?
C220 N203 H23N 114.0(13) . . ?
C221 N203 H23N 117.3(13) . . ?
C227 N204 C226 123.91(12) . . ?
C227 N204 H24N 118.5(12) . . ?
C226 N204 H24N 115.1(12) . . ?
C219 N205 C215 117.34(12) . . ?
C202 C201 C206 120.55(16) . . ?
C202 C201 H20A 119.7 . . ?
C206 C201 H20A 119.7 . . ?
C201 C202 C203 119.89(17) . . ?
C201 C202 H202 120.1 . . ?
C203 C202 H202 120.1 . . ?
C204 C203 C202 120.11(16) . . ?
C204 C203 H203 119.9 . . ?
C202 C203 H203 119.9 . . ?
C203 C204 C205 120.43(16) . . ?
C203 C204 H20B 119.8 . . ?
C205 C204 H20B 119.8 . . ?
C206 C205 C204 119.50(16) . . ?
C206 C205 H205 120.2 . . ?
C204 C205 H205 120.2 . . ?
C201 C206 C205 119.47(15) . . ?
C201 C206 C207 116.10(14) . . ?
C205 C206 C207 124.31(14) . . ?
O201 C207 N201 121.81(14) . . ?
O201 C207 C206 120.55(14) . . ?
N201 C207 C206 117.53(13) . . ?
C209 C208 C213 119.70(14) . . ?
C209 C208 N201 119.32(13) . . ?
C213 C208 N201 120.71(13) . . ?
C210 C209 C208 120.18(14) . . ?
C210 C209 H209 119.9 . . ?
C208 C209 H209 119.9 . . ?
C211 C210 C209 120.05(15) . . ?
C211 C210 H210 120.0 . . ?
C209 C210 H210 120.0 . . ?
C210 C211 C212 120.15(15) . . ?
C210 C211 H211 119.9 . . ?
C212 C211 H211 119.9 . . ?
C211 C212 C213 120.04(15) . . ?
C211 C212 H212 120.0 . . ?
C213 C212 H212 120.0 . . ?
C212 C213 C208 119.76(14) . . ?
C212 C213 N202 121.29(14) . . ?
C208 C213 N202 118.95(13) . . ?
O202 C214 N202 124.52(14) . . ?
O202 C214 C215 121.48(13) . . ?
N202 C214 C215 113.90(12) . . ?
N205 C215 C216 123.62(14) . . ?
N205 C215 C214 116.85(12) . . ?
C216 C215 C214 119.45(13) . . ?
C217 C216 C215 118.06(14) . . ?
C217 C216 H216 121.0 . . ?
C215 C216 H216 121.0 . . ?
C218 C217 C216 119.27(14) . . ?
C218 C217 H217 120.4 . . ?
C216 C217 H217 120.4 . . ?
C217 C218 C219 118.22(14) . . ?
C217 C218 H218 120.9 . . ?
C219 C218 H218 120.9 . . ?
N205 C219 C218 123.42(13) . . ?
N205 C219 C220 117.93(12) . . ?
C218 C219 C220 118.65(13) . . ?
O203 C220 N203 125.78(14) . . ?
O203 C220 C219 120.53(13) . . ?
N203 C220 C219 113.68(12) . . ?
C222 C221 N203 122.63(13) . . ?
C222 C221 C226 119.01(13) . . ?
N203 C221 C226 118.27(13) . . ?
C223 C222 C221 120.19(14) . . ?
C223 C222 H222 119.9 . . ?
C221 C222 H222 119.9 . . ?
C222 C223 C224 120.81(14) . . ?
C222 C223 H223 119.6 . . ?
C224 C223 H223 119.6 . . ?
C225 C224 C223 119.22(14) . . ?
C225 C224 H224 120.4 . . ?
C223 C224 H224 120.4 . . ?
C224 C225 C226 120.86(14) . . ?
C224 C225 H225 119.6 . . ?
C226 C225 H225 119.6 . . ?
C225 C226 C221 119.82(13) . . ?
C225 C226 N204 118.76(13) . . ?
C221 C226 N204 121.34(13) . . ?
O204 C227 N204 123.24(13) . . ?
O204 C227 C228 121.76(13) . . ?
N204 C227 C228 115.00(12) . . ?
C233 C228 C229 120.16(14) . . ?
C233 C228 C227 122.61(13) . . ?
C229 C228 C227 117.21(14) . . ?
C230 C229 C228 120.00(16) . . ?
C230 C229 H229 120.0 . . ?
C228 C229 H229 120.0 . . ?
C229 C230 C231 120.12(16) . . ?
C229 C230 H230 119.9 . . ?
C231 C230 H230 119.9 . . ?
C230 C231 C232 120.05(15) . . ?
C230 C231 H231 120.0 . . ?
C232 C231 H231 120.0 . . ?
C231 C232 C233 120.04(16) . . ?
C231 C232 H232 120.0 . . ?
C233 C232 H232 120.0 . . ?
C228 C233 C232 119.60(15) . . ?
C228 C233 H233 120.2 . . ?
C232 C233 H233 120.2 . . ?
C307 N301 C308 119.85(13) . . ?
C307 N301 H31N 121.6(13) . . ?
C308 N301 H31N 116.6(13) . . ?
C314 N302 C313 126.24(13) . . ?
C314 N302 H32N 115.2(12) . . ?
C313 N302 H32N 118.5(12) . . ?
C320 N303 C321 126.84(13) . . ?
C320 N303 H33N 116.6(13) . . ?
C321 N303 H33N 116.5(13) . . ?
C327 N304 C326 127.97(12) . . ?
C327 N304 H34N 118.1(12) . . ?
C326 N304 H34N 113.0(12) . . ?
C319 N305 C315 117.41(12) . . ?
C302 C301 C306 120.56(16) . . ?
C302 C301 H30A 119.7 . . ?
C306 C301 H30A 119.7 . . ?
C303 C302 C301 119.97(16) . . ?
C303 C302 H302 120.0 . . ?
C301 C302 H302 120.0 . . ?
C302 C303 C304 120.07(17) . . ?
C302 C303 H30B 120.0 . . ?
C304 C303 H30B 120.0 . . ?
C303 C304 C305 120.27(18) . . ?
C303 C304 H30C 119.9 . . ?
C305 C304 H30C 119.9 . . ?
C304 C305 C306 120.04(17) . . ?
C304 C305 H305 120.0 . . ?
C306 C305 H305 120.0 . . ?
C305 C306 C301 119.08(15) . . ?
C305 C306 C307 122.98(14) . . ?
C301 C306 C307 117.72(14) . . ?
O301 C307 N301 121.33(14) . . ?
O301 C307 C306 121.58(14) . . ?
N301 C307 C306 117.04(13) . . ?
C309 C308 C313 120.10(14) . . ?
C309 C308 N301 120.59(14) . . ?
C313 C308 N301 119.27(13) . . ?
C308 C309 C310 119.50(16) . . ?
C308 C309 H309 120.2 . . ?
C310 C309 H309 120.2 . . ?
C311 C310 C309 120.32(15) . . ?
C311 C310 H310 119.8 . . ?
C309 C310 H310 119.8 . . ?
C310 C311 C312 120.82(15) . . ?
C310 C311 H311 119.6 . . ?
C312 C311 H311 119.6 . . ?
C311 C312 C313 119.06(16) . . ?
C311 C312 H312 120.5 . . ?
C313 C312 H312 120.5 . . ?
C312 C313 C308 120.13(14) . . ?
C312 C313 N302 122.06(14) . . ?
C308 C313 N302 117.80(13) . . ?
O302 C314 N302 125.04(14) . . ?
O302 C314 C315 120.88(14) . . ?
N302 C314 C315 114.00(12) . . ?
N305 C315 C316 123.50(14) . . ?
N305 C315 C314 116.95(13) . . ?
C316 C315 C314 119.48(13) . . ?
C317 C316 C315 118.34(14) . . ?
C317 C316 H316 120.8 . . ?
C315 C316 H316 120.8 . . ?
C318 C317 C316 119.02(14) . . ?
C318 C317 H317 120.5 . . ?
C316 C317 H317 120.5 . . ?
C317 C318 C319 118.40(14) . . ?
C317 C318 H318 120.8 . . ?
C319 C318 H318 120.8 . . ?
N305 C319 C318 123.31(14) . . ?
N305 C319 C320 117.55(13) . . ?
C318 C319 C320 119.14(13) . . ?
O303 C320 N303 126.03(14) . . ?
O303 C320 C319 120.50(13) . . ?
N303 C320 C319 113.47(12) . . ?
C322 C321 C326 118.75(13) . . ?
C322 C321 N303 120.95(13) . . ?
C326 C321 N303 120.30(13) . . ?
C323 C322 C321 120.96(14) . . ?
C323 C322 H322 119.5 . . ?
C321 C322 H322 119.5 . . ?
C322 C323 C324 120.17(14) . . ?
C322 C323 H323 119.9 . . ?
C324 C323 H323 119.9 . . ?
C325 C324 C323 119.31(14) . . ?
C325 C324 H324 120.3 . . ?
C323 C324 H324 120.3 . . ?
C324 C325 C326 121.39(14) . . ?
C324 C325 H325 119.3 . . ?
C326 C325 H325 119.3 . . ?
C325 C326 C321 119.32(13) . . ?
C325 C326 N304 116.30(13) . . ?
C321 C326 N304 124.20(13) . . ?
O304 C327 N304 122.52(13) . . ?
O304 C327 C328 121.27(13) . . ?
N304 C327 C328 116.22(12) . . ?
C329 C328 C333 119.56(13) . . ?
C329 C328 C327 117.74(13) . . ?
C333 C328 C327 122.69(13) . . ?
C330 C329 C328 120.49(14) . . ?
C330 C329 H329 119.8 . . ?
C328 C329 H329 119.8 . . ?
C329 C330 C331 119.73(14) . . ?
C329 C330 H330 120.1 . . ?
C331 C330 H330 120.1 . . ?
C332 C331 C330 120.20(14) . . ?
C332 C331 H331 119.9 . . ?
C330 C331 H331 119.9 . . ?
C333 C332 C331 120.20(14) . . ?
C333 C332 H332 119.9 . . ?
C331 C332 H332 119.9 . . ?
C332 C333 C328 119.81(14) . . ?
C332 C333 H333 120.1 . . ?
C328 C333 H333 120.1 . . ?

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
C106 C101 C102 C103 0.1(3) . . . . ?
C101 C102 C103 C104 -0.7(3) . . . . ?
C102 C103 C104 C105 0.6(3) . . . . ?
C103 C104 C105 C106 0.0(2) . . . . ?
C104 C105 C106 C101 -0.5(2) . . . . ?
C104 C105 C106 C107 176.34(14) . . . . ?
C102 C101 C106 C105 0.5(2) . . . . ?
C102 C101 C106 C107 -176.18(16) . . . . ?
C108 N101 C107 O101 -12.4(2) . . . . ?
C108 N101 C107 C106 163.78(13) . . . . ?
C105 C106 C107 O101 15.9(2) . . . . ?
C101 C106 C107 O101 -167.38(15) . . . . ?
C105 C106 C107 N101 -160.39(14) . . . . ?
C101 C106 C107 N101 16.3(2) . . . . ?
C107 N101 C108 C109 53.3(2) . . . . ?
C107 N101 C108 C113 -126.26(16) . . . . ?
C113 C108 C109 C110 1.2(2) . . . . ?
N101 C108 C109 C110 -178.29(14) . . . . ?
C108 C109 C110 C111 -0.1(2) . . . . ?
C109 C110 C111 C112 -0.5(2) . . . . ?
C110 C111 C112 C113 0.1(2) . . . . ?
C111 C112 C113 C108 1.0(2) . . . . ?
C111 C112 C113 N102 -178.33(14) . . . . ?
C109 C108 C113 C112 -1.6(2) . . . . ?
N101 C108 C113 C112 177.89(13) . . . . ?
C109 C108 C113 N102 177.68(13) . . . . ?
N101 C108 C113 N102 -2.8(2) . . . . ?
C114 N102 C113 C112 -41.6(2) . . . . ?
C114 N102 C113 C108 139.10(15) . . . . ?
C113 N102 C114 O102 11.3(3) . . . . ?
C113 N102 C114 C115 -166.38(13) . . . . ?
C119 N105 C115 C116 0.2(2) . . . . ?
C119 N105 C115 C114 176.65(12) . . . . ?
O102 C114 C115 N105 171.27(14) . . . . ?
N102 C114 C115 N105 -10.91(18) . . . . ?
O102 C114 C115 C116 -12.1(2) . . . . ?
N102 C114 C115 C116 165.70(13) . . . . ?
N105 C115 C116 C117 2.2(2) . . . . ?
C114 C115 C116 C117 -174.20(13) . . . . ?
C115 C116 C117 C118 -1.7(2) . . . . ?
C116 C117 C118 C119 -0.9(2) . . . . ?
C115 N105 C119 C118 -3.1(2) . . . . ?
C115 N105 C119 C120 176.71(12) . . . . ?
C117 C118 C119 N105 3.5(2) . . . . ?
C117 C118 C119 C120 -176.29(13) . . . . ?
C121 N103 C120 O103 -6.0(3) . . . . ?
C121 N103 C120 C119 175.50(13) . . . . ?
N105 C119 C120 O103 177.97(13) . . . . ?
C118 C119 C120 O103 -2.3(2) . . . . ?
N105 C119 C120 N103 -3.44(19) . . . . ?
C118 C119 C120 N103 176.33(13) . . . . ?
C120 N103 C121 C122 -23.0(2) . . . . ?
C120 N103 C121 C126 157.58(15) . . . . ?
C126 C121 C122 C123 -0.9(2) . . . . ?
N103 C121 C122 C123 179.70(15) . . . . ?
C121 C122 C123 C124 2.0(3) . . . . ?
C122 C123 C124 C125 -0.9(3) . . . . ?
C123 C124 C125 C126 -1.3(2) . . . . ?
C124 C125 C126 C121 2.5(2) . . . . ?
C124 C125 C126 N104 -173.90(14) . . . . ?
C122 C121 C126 C125 -1.3(2) . . . . ?
N103 C121 C126 C125 178.10(13) . . . . ?
C122 C121 C126 N104 174.79(14) . . . . ?
N103 C121 C126 N104 -5.8(2) . . . . ?
C127 N104 C126 C125 -127.56(16) . . . . ?
C127 N104 C126 C121 56.2(2) . . . . ?
C126 N104 C127 O104 -4.8(2) . . . . ?
C126 N104 C127 C128 174.84(13) . . . . ?
O104 C127 C128 C129 24.8(2) . . . . ?
N104 C127 C128 C129 -154.81(13) . . . . ?
O104 C127 C128 C133 -155.56(14) . . . . ?
N104 C127 C128 C133 24.8(2) . . . . ?
C133 C128 C129 C130 -1.0(2) . . . . ?
C127 C128 C129 C130 178.67(13) . . . . ?
C128 C129 C130 C131 0.7(2) . . . . ?
C129 C130 C131 C132 0.2(2) . . . . ?
C130 C131 C132 C133 -0.9(2) . . . . ?
C131 C132 C133 C128 0.6(2) . . . . ?
C129 C128 C133 C132 0.3(2) . . . . ?
C127 C128 C133 C132 -179.33(14) . . . . ?
C206 C201 C202 C203 -2.2(3) . . . . ?
C201 C202 C203 C204 0.8(3) . . . . ?
C202 C203 C204 C205 1.2(3) . . . . ?
C203 C204 C205 C206 -1.7(2) . . . . ?
C202 C201 C206 C205 1.6(2) . . . . ?
C202 C201 C206 C207 -174.68(15) . . . . ?
C204 C205 C206 C201 0.3(2) . . . . ?
C204 C205 C206 C207 176.29(14) . . . . ?
C208 N201 C207 O201 7.5(2) . . . . ?
C208 N201 C207 C206 -168.66(13) . . . . ?
C201 C206 C207 O201 -19.4(2) . . . . ?
C205 C206 C207 O201 164.52(14) . . . . ?
C201 C206 C207 N201 156.79(14) . . . . ?
C205 C206 C207 N201 -19.3(2) . . . . ?
C207 N201 C208 C209 -125.91(16) . . . . ?
C207 N201 C208 C213 60.0(2) . . . . ?
C213 C208 C209 C210 3.0(2) . . . . ?
N201 C208 C209 C210 -171.16(14) . . . . ?
C208 C209 C210 C211 -0.1(2) . . . . ?
C209 C210 C211 C212 -2.0(3) . . . . ?
C210 C211 C212 C213 1.1(2) . . . . ?
C211 C212 C213 C208 1.8(2) . . . . ?
C211 C212 C213 N202 -178.24(14) . . . . ?
C209 C208 C213 C212 -3.8(2) . . . . ?
N201 C208 C213 C212 170.26(14) . . . . ?
C209 C208 C213 N202 176.19(13) . . . . ?
N201 C208 C213 N202 -9.7(2) . . . . ?
C214 N202 C213 C212 -56.3(2) . . . . ?
C214 N202 C213 C208 123.70(16) . . . . ?
C213 N202 C214 O202 4.8(2) . . . . ?
C213 N202 C214 C215 -171.60(13) . . . . ?
C219 N205 C215 C216 -1.7(2) . . . . ?
C219 N205 C215 C214 174.96(12) . . . . ?
O202 C214 C215 N205 177.52(13) . . . . ?
N202 C214 C215 N205 -5.93(18) . . . . ?
O202 C214 C215 C216 -5.7(2) . . . . ?
N202 C214 C215 C216 170.89(13) . . . . ?
N205 C215 C216 C217 1.9(2) . . . . ?
C214 C215 C216 C217 -174.69(13) . . . . ?
C215 C216 C217 C218 0.2(2) . . . . ?
C216 C217 C218 C219 -2.2(2) . . . . ?
C215 N205 C219 C218 -0.6(2) . . . . ?
C215 N205 C219 C220 179.95(12) . . . . ?
C217 C218 C219 N205 2.5(2) . . . . ?
C217 C218 C219 C220 -177.99(13) . . . . ?
C221 N203 C220 O203 -4.7(3) . . . . ?
C221 N203 C220 C219 175.57(14) . . . . ?
N205 C219 C220 O203 168.04(14) . . . . ?
C218 C219 C220 O203 -11.5(2) . . . . ?
N205 C219 C220 N203 -12.20(19) . . . . ?
C218 C219 C220 N203 168.29(13) . . . . ?
C220 N203 C221 C222 -7.1(3) . . . . ?
C220 N203 C221 C226 176.37(14) . . . . ?
N203 C221 C222 C223 -174.34(16) . . . . ?
C226 C221 C222 C223 2.1(2) . . . . ?
C221 C222 C223 C224 0.7(3) . . . . ?
C222 C223 C224 C225 -2.0(3) . . . . ?
C223 C224 C225 C226 0.3(2) . . . . ?
C224 C225 C226 C221 2.5(2) . . . . ?
C224 C225 C226 N204 179.21(13) . . . . ?
C222 C221 C226 C225 -3.7(2) . . . . ?
N203 C221 C226 C225 172.88(13) . . . . ?
C222 C221 C226 N204 179.70(14) . . . . ?
N203 C221 C226 N204 -3.7(2) . . . . ?
C227 N204 C226 C225 122.44(15) . . . . ?
C227 N204 C226 C221 -60.95(19) . . . . ?
C226 N204 C227 O204 8.5(2) . . . . ?
C226 N204 C227 C228 -172.54(12) . . . . ?
O204 C227 C228 C233 143.96(15) . . . . ?
N204 C227 C228 C233 -35.06(19) . . . . ?
O204 C227 C228 C229 -34.9(2) . . . . ?
N204 C227 C228 C229 146.11(13) . . . . ?
C233 C228 C229 C230 1.5(2) . . . . ?
C227 C228 C229 C230 -179.68(14) . . . . ?
C228 C229 C230 C231 -0.8(2) . . . . ?
C229 C230 C231 C232 -0.6(2) . . . . ?
C230 C231 C232 C233 1.4(2) . . . . ?
C229 C228 C233 C232 -0.7(2) . . . . ?
C227 C228 C233 C232 -179.45(13) . . . . ?
C231 C232 C233 C228 -0.8(2) . . . . ?
C306 C301 C302 C303 0.1(3) . . . . ?
C301 C302 C303 C304 -1.2(3) . . . . ?
C302 C303 C304 C305 0.9(3) . . . . ?
C303 C304 C305 C306 0.4(3) . . . . ?
C304 C305 C306 C301 -1.5(3) . . . . ?
C304 C305 C306 C307 172.95(17) . . . . ?
C302 C301 C306 C305 1.2(2) . . . . ?
C302 C301 C306 C307 -173.51(15) . . . . ?
C308 N301 C307 O301 11.7(2) . . . . ?
C308 N301 C307 C306 -165.61(13) . . . . ?
C305 C306 C307 O301 -161.30(17) . . . . ?
C301 C306 C307 O301 13.2(2) . . . . ?
C305 C306 C307 N301 16.0(2) . . . . ?
C301 C306 C307 N301 -169.51(14) . . . . ?
C307 N301 C308 C309 -83.37(19) . . . . ?
C307 N301 C308 C313 94.32(17) . . . . ?
C313 C308 C309 C310 -1.7(2) . . . . ?
N301 C308 C309 C310 175.97(15) . . . . ?
C308 C309 C310 C311 -0.8(3) . . . . ?
C309 C310 C311 C312 2.1(3) . . . . ?
C310 C311 C312 C313 -0.9(2) . . . . ?
C311 C312 C313 C308 -1.6(2) . . . . ?
C311 C312 C313 N302 177.76(14) . . . . ?
C309 C308 C313 C312 2.9(2) . . . . ?
N301 C308 C313 C312 -174.81(13) . . . . ?
C309 C308 C313 N302 -176.48(14) . . . . ?
N301 C308 C313 N302 5.8(2) . . . . ?
C314 N302 C313 C312 39.1(2) . . . . ?
C314 N302 C313 C308 -141.58(15) . . . . ?
C313 N302 C314 O302 -5.2(2) . . . . ?
C313 N302 C314 C315 171.74(13) . . . . ?
C319 N305 C315 C316 0.1(2) . . . . ?
C319 N305 C315 C314 -176.95(12) . . . . ?
O302 C314 C315 N305 -177.73(13) . . . . ?
N302 C314 C315 N305 5.22(18) . . . . ?
O302 C314 C315 C316 5.1(2) . . . . ?
N302 C314 C315 C316 -171.93(13) . . . . ?
N305 C315 C316 C317 -1.2(2) . . . . ?
C314 C315 C316 C317 175.74(14) . . . . ?
C315 C316 C317 C318 0.9(2) . . . . ?
C316 C317 C318 C319 0.5(2) . . . . ?
C315 N305 C319 C318 1.4(2) . . . . ?
C315 N305 C319 C320 -178.35(12) . . . . ?
C317 C318 C319 N305 -1.7(2) . . . . ?
C317 C318 C319 C320 178.03(14) . . . . ?
C321 N303 C320 O303 0.8(2) . . . . ?
C321 N303 C320 C319 179.56(13) . . . . ?
N305 C319 C320 O303 -173.86(14) . . . . ?
C318 C319 C320 O303 6.3(2) . . . . ?
N305 C319 C320 N303 7.31(19) . . . . ?
C318 C319 C320 N303 -172.48(13) . . . . ?
C320 N303 C321 C322 24.2(2) . . . . ?
C320 N303 C321 C326 -155.13(14) . . . . ?
C326 C321 C322 C323 2.9(2) . . . . ?
N303 C321 C322 C323 -176.52(14) . . . . ?
C321 C322 C323 C324 -2.1(2) . . . . ?
C322 C323 C324 C325 -0.8(2) . . . . ?
C323 C324 C325 C326 2.9(2) . . . . ?
C324 C325 C326 C321 -2.2(2) . . . . ?
C324 C325 C326 N304 173.20(14) . . . . ?
C322 C321 C326 C325 -0.7(2) . . . . ?
N303 C321 C326 C325 178.67(13) . . . . ?
C322 C321 C326 N304 -175.72(14) . . . . ?
N303 C321 C326 N304 3.7(2) . . . . ?
C327 N304 C326 C325 132.00(15) . . . . ?
C327 N304 C326 C321 -52.9(2) . . . . ?
C326 N304 C327 O304 5.9(2) . . . . ?
C326 N304 C327 C328 -174.07(13) . . . . ?
O304 C327 C328 C329 -23.7(2) . . . . ?
N304 C327 C328 C329 156.25(13) . . . . ?
O304 C327 C328 C333 156.40(14) . . . . ?
N304 C327 C328 C333 -23.6(2) . . . . ?
C333 C328 C329 C330 -0.4(2) . . . . ?
C327 C328 C329 C330 179.75(13) . . . . ?
C328 C329 C330 C331 0.7(2) . . . . ?
C329 C330 C331 C332 -0.3(2) . . . . ?
C330 C331 C332 C333 -0.5(2) . . . . ?
C331 C332 C333 C328 0.9(2) . . . . ?
C329 C328 C333 C332 -0.5(2) . . . . ?
C327 C328 C333 C332 179.43(13) . . . . ?

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
N101 H11N O104 0.87(2) 2.10(2) 2.9090(17) 153.9(18) .
N102 H12N O104 0.88(2) 2.35(2) 3.0990(17) 143.8(17) .
N102 H12N N105 0.88(2) 2.15(2) 2.6417(18) 114.5(16) .
N103 H13N O104 0.84(2) 2.09(2) 2.7975(17) 142.1(18) .
N103 H13N N105 0.84(2) 2.208(19) 2.6579(17) 113.7(16) .
N104 H14N O302 0.88(2) 1.99(2) 2.8365(16) 162.4(17) 2_656
N201 H21N O301 0.90(2) 2.19(2) 2.9793(17) 144.9(17) 1_565
N202 H22N O201 0.88(2) 2.14(2) 2.8375(17) 136.2(16) .
N203 H23N N205 0.85(2) 2.241(19) 2.6870(17) 112.8(16) .
N204 H24N O101 0.882(19) 2.043(19) 2.8488(17) 151.4(16) 2_666
N301 H31N O304 0.87(2) 2.16(2) 2.9717(16) 154.8(18) .
N302 H32N O304 0.92(2) 2.36(2) 3.1983(16) 150.6(16) .
N302 H32N N305 0.92(2) 2.185(19) 2.6595(17) 111.0(14) .
N303 H33N O304 0.86(2) 2.05(2) 2.7888(16) 143.5(17) .
N303 H33N N305 0.86(2) 2.240(19) 2.6700(17) 111.0(15) .
N304 H34N O202 0.856(19) 2.08(2) 2.9302(16) 169.3(17) 2_665

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.049

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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-DMA-at
_database_code_depnum_ccdc_archive 'CCDC 1436660'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H25 N5 O4, C4 H9 N O'
_chemical_formula_sum            'C37 H34 N6 O5'
_chemical_formula_weight         642.70

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

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

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

_cell_length_a                   14.34241(19)
_cell_length_b                   19.5568(2)
_cell_length_c                   11.34410(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.0477(12)
_cell_angle_gamma                90
_cell_volume                     3173.98(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13494
_cell_measurement_theta_min      2.5150
_cell_measurement_theta_max      28.8440

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_T_min  0.66595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            35938
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.079
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7844
_reflns_number_gt                6462
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+1.4543P] 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         7844
_refine_ls_number_parameters     466
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1044
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.97467(7) 0.44372(5) 0.34894(11) 0.0413(3) Uani 1 1 d . . . . .
O2 O 0.58461(8) 0.38227(5) 0.19575(9) 0.0357(2) Uani 1 1 d . . . . .
O3 O 0.68941(7) 0.62735(5) -0.22864(8) 0.0279(2) Uani 1 1 d . . . . .
O4 O 0.74121(6) 0.62615(4) 0.20827(7) 0.02509(19) Uani 1 1 d . . . . .
N1 N 0.85969(8) 0.52214(6) 0.31590(10) 0.0268(2) Uani 1 1 d . . . . .
H1N H 0.8398(12) 0.5588(9) 0.2746(15) 0.040 Uiso 1 1 d . U . . .
N2 N 0.68914(8) 0.46996(6) 0.22672(10) 0.0281(2) Uani 1 1 d . . . . .
H2N H 0.7117(12) 0.5026(9) 0.1896(16) 0.042 Uiso 1 1 d . U . . .
N3 N 0.72762(8) 0.63567(5) -0.02919(9) 0.0239(2) Uani 1 1 d . . . . .
H3N H 0.7195(11) 0.6143(8) 0.0371(15) 0.036 Uiso 1 1 d . U . . .
N4 N 0.71224(7) 0.73680(5) 0.15697(9) 0.0226(2) Uani 1 1 d . . . . .
H4N H 0.6939(11) 0.7759(9) 0.1870(14) 0.034 Uiso 1 1 d . U . . .
N5 N 0.65474(7) 0.51409(5) 0.00781(9) 0.0213(2) Uani 1 1 d . . . . .
C1 C 1.06731(10) 0.49503(9) 0.15493(15) 0.0402(4) Uani 1 1 d . . . . .
H1 H 1.0781 0.4484 0.1749 0.048 Uiso 1 1 calc R U . . .
C2 C 1.11901(11) 0.52588(11) 0.07165(16) 0.0508(5) Uani 1 1 d . . . . .
H2 H 1.1642 0.5001 0.0334 0.061 Uiso 1 1 calc R U . . .
C3 C 1.10544(12) 0.59402(11) 0.04364(16) 0.0532(5) Uani 1 1 d . . . . .
H3 H 1.1425 0.6154 -0.0119 0.064 Uiso 1 1 calc R U . . .
C4 C 1.03783(13) 0.63100(10) 0.09669(17) 0.0528(5) Uani 1 1 d . . . . .
H4 H 1.0278 0.6777 0.0768 0.063 Uiso 1 1 calc R U . . .
C5 C 0.98459(11) 0.60000(8) 0.17896(15) 0.0395(3) Uani 1 1 d . . . . .
H5 H 0.9376 0.6254 0.2145 0.047 Uiso 1 1 calc R U . . .
C6 C 0.99958(9) 0.53181(7) 0.20969(12) 0.0289(3) Uani 1 1 d . . . . .
C7 C 0.94473(9) 0.49510(7) 0.29836(12) 0.0274(3) Uani 1 1 d . . . . .
C8 C 0.79733(9) 0.49335(6) 0.39508(11) 0.0244(3) Uani 1 1 d . . . . .
C9 C 0.81913(10) 0.49454(7) 0.51607(12) 0.0315(3) Uani 1 1 d . . . . .
H9 H 0.8765 0.5140 0.5468 0.038 Uiso 1 1 calc R U . . .
C10 C 0.75740(11) 0.46733(8) 0.59238(13) 0.0373(3) Uani 1 1 d . . . . .
H10 H 0.7724 0.4680 0.6753 0.045 Uiso 1 1 calc R U . . .
C11 C 0.67393(11) 0.43925(8) 0.54721(12) 0.0351(3) Uani 1 1 d . . . . .
H11 H 0.6321 0.4201 0.5995 0.042 Uiso 1 1 calc R U . . .
C12 C 0.65066(10) 0.43874(7) 0.42688(12) 0.0296(3) Uani 1 1 d . . . . .
H12 H 0.5928 0.4198 0.3970 0.036 Uiso 1 1 calc R U . . .
C13 C 0.71194(9) 0.46600(6) 0.34951(11) 0.0243(3) Uani 1 1 d . . . . .
C14 C 0.62742(9) 0.43112(6) 0.16057(11) 0.0242(3) Uani 1 1 d . . . . .
C15 C 0.61346(9) 0.45527(6) 0.03383(11) 0.0224(2) Uani 1 1 d . . . . .
C16 C 0.55805(9) 0.41832(7) -0.04868(12) 0.0274(3) Uani 1 1 d . . . . .
H16 H 0.5299 0.3765 -0.0276 0.033 Uiso 1 1 calc R U . . .
C17 C 0.54482(10) 0.44387(7) -0.16265(12) 0.0292(3) Uani 1 1 d . . . . .
H17 H 0.5074 0.4197 -0.2212 0.035 Uiso 1 1 calc R U . . .
C18 C 0.58691(9) 0.50520(7) -0.19032(11) 0.0253(3) Uani 1 1 d . . . . .
H18 H 0.5786 0.5239 -0.2676 0.030 Uiso 1 1 calc R U . . .
C19 C 0.64146(8) 0.53843(6) -0.10213(10) 0.0211(2) Uani 1 1 d . . . . .
C20 C 0.68878(8) 0.60530(6) -0.12729(10) 0.0215(2) Uani 1 1 d . . . . .
C21 C 0.78347(9) 0.69531(6) -0.02353(11) 0.0221(2) Uani 1 1 d . . . . .
C22 C 0.84801(9) 0.70661(7) -0.10767(11) 0.0265(3) Uani 1 1 d . . . . .
H22 H 0.8554 0.6733 -0.1673 0.032 Uiso 1 1 calc R U . . .
C23 C 0.90145(9) 0.76540(7) -0.10575(12) 0.0297(3) Uani 1 1 d . . . . .
H23 H 0.9448 0.7725 -0.1642 0.036 Uiso 1 1 calc R U . . .
C24 C 0.89189(10) 0.81408(7) -0.01867(12) 0.0304(3) Uani 1 1 d . . . . .
H24 H 0.9276 0.8550 -0.0179 0.036 Uiso 1 1 calc R U . . .
C25 C 0.82976(10) 0.80255(6) 0.06724(12) 0.0274(3) Uani 1 1 d . . . . .
H25 H 0.8235 0.8358 0.1272 0.033 Uiso 1 1 calc R U . . .
C26 C 0.77619(8) 0.74307(6) 0.06737(11) 0.0220(2) Uani 1 1 d . . . . .
C27 C 0.69977(8) 0.68083(6) 0.22384(10) 0.0207(2) Uani 1 1 d . . . . .
C28 C 0.63216(8) 0.68703(6) 0.31735(10) 0.0211(2) Uani 1 1 d . . . . .
C29 C 0.63806(9) 0.63886(6) 0.40846(11) 0.0253(3) Uani 1 1 d . . . . .
H29 H 0.6844 0.6041 0.4095 0.030 Uiso 1 1 calc R U . . .
C30 C 0.57665(10) 0.64159(7) 0.49720(12) 0.0307(3) Uani 1 1 d . . . . .
H30 H 0.5815 0.6090 0.5595 0.037 Uiso 1 1 calc R U . . .
C31 C 0.50822(10) 0.69163(7) 0.49556(12) 0.0303(3) Uani 1 1 d . . . . .
H31 H 0.4660 0.6932 0.5563 0.036 Uiso 1 1 calc R U . . .
C32 C 0.50145(9) 0.73937(7) 0.40539(13) 0.0303(3) Uani 1 1 d . . . . .
H32 H 0.4544 0.7736 0.4042 0.036 Uiso 1 1 calc R U . . .
C33 C 0.56321(9) 0.73740(6) 0.31652(12) 0.0265(3) Uani 1 1 d . . . . .
H33 H 0.5585 0.7704 0.2550 0.032 Uiso 1 1 calc R U . . .
O10A O 0.71426(10) 0.21906(8) 0.49419(12) 0.0628(4) Uani 0.85 1 d . . P A 1
N10A N 0.80727(12) 0.28179(9) 0.38541(17) 0.0382(4) Uani 0.85 1 d . . P A 1
C10A C 0.69805(19) 0.20497(15) 0.2821(2) 0.0907(9) Uani 0.85 1 d . . P A 1
H10A H 0.7405 0.1699 0.2553 0.136 Uiso 0.85 1 calc R U P A 1
H10B H 0.6895 0.2408 0.2218 0.136 Uiso 0.85 1 calc R U P A 1
H10C H 0.6375 0.1842 0.2952 0.136 Uiso 0.85 1 calc R U P A 1
C11A C 0.73865(14) 0.23555(12) 0.3948(2) 0.0439(4) Uani 0.85 1 d . . P A 1
C12A C 0.84119(16) 0.30203(11) 0.27333(18) 0.0637(6) Uani 0.85 1 d . . P A 1
H12A H 0.8923 0.2717 0.2541 0.096 Uiso 0.85 1 calc R U P A 1
H12B H 0.8639 0.3493 0.2788 0.096 Uiso 0.85 1 calc R U P A 1
H12C H 0.7902 0.2988 0.2113 0.096 Uiso 0.85 1 calc R U P A 1
C13A C 0.85135(14) 0.30970(10) 0.49540(17) 0.0528(4) Uani 0.85 1 d . . P A 1
H13A H 0.8035 0.3180 0.5513 0.079 Uiso 0.85 1 calc R U P A 1
H13B H 0.8827 0.3528 0.4788 0.079 Uiso 0.85 1 calc R U P A 1
H13C H 0.8973 0.2770 0.5298 0.079 Uiso 0.85 1 calc R U P A 1
O10B O 0.71426(10) 0.21906(8) 0.49419(12) 0.0628(4) Uani 0.15 1 d . . P B 2
N10B N 0.7705(8) 0.2587(6) 0.3398(11) 0.045(2) Uani 0.15 1 d . . P B 2
C10B C 0.69805(19) 0.20497(15) 0.2821(2) 0.0907(9) Uani 0.15 1 d . . P B 2
H10D H 0.6989 0.2069 0.1959 0.136 Uiso 0.15 1 calc R U P B 2
H10E H 0.7153 0.1589 0.3098 0.136 Uiso 0.15 1 calc R U P B 2
H10F H 0.6352 0.2160 0.3051 0.136 Uiso 0.15 1 calc R U P B 2
C11B C 0.7751(8) 0.2604(6) 0.4560(11) 0.040(2) Uani 0.15 1 d . . P B 2
C12B C 0.84119(16) 0.30203(11) 0.27333(18) 0.0637(6) Uani 0.15 1 d . . P B 2
H12D H 0.8292 0.2955 0.1880 0.096 Uiso 0.15 1 calc R U P B 2
H12E H 0.8338 0.3505 0.2927 0.096 Uiso 0.15 1 calc R U P B 2
H12F H 0.9051 0.2874 0.2975 0.096 Uiso 0.15 1 calc R U P B 2
C13B C 0.85135(14) 0.30970(10) 0.49540(17) 0.0528(4) Uani 0.15 1 d . . P B 2
H13D H 0.8782 0.3295 0.4260 0.079 Uiso 0.15 1 calc R U P B 2
H13E H 0.8254 0.3463 0.5422 0.079 Uiso 0.15 1 calc R U P B 2
H13F H 0.9002 0.2855 0.5437 0.079 Uiso 0.15 1 calc R U P B 2


_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 C7 1.2200(16) . ?
O2 C14 1.2179(15) . ?
O3 C20 1.2286(15) . ?
O4 C27 1.2421(14) . ?
N1 C7 1.3569(17) . ?
N1 C8 1.4273(16) . ?
N1 H1N 0.892(18) . ?
N2 C14 1.3528(17) . ?
N2 C13 1.4103(16) . ?
N2 H2N 0.842(18) . ?
N3 C20 1.3469(16) . ?
N3 C21 1.4137(15) . ?
N3 H3N 0.876(17) . ?
N4 C27 1.3508(15) . ?
N4 C26 1.4216(15) . ?
N4 H4N 0.885(17) . ?
N5 C19 1.3359(15) . ?
N5 C15 1.3361(15) . ?
C1 C2 1.380(2) . ?
C1 C6 1.390(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.5026(19) . ?
C8 C9 1.3862(19) . ?
C8 C13 1.4013(18) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3822(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3914(17) . ?
C12 H12 0.9500 . ?
C14 C15 1.5132(17) . ?
C15 C16 1.3874(18) . ?
C16 C17 1.3866(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.3887(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3873(18) . ?
C18 H18 0.9500 . ?
C19 C20 1.5100(16) . ?
C21 C22 1.3933(17) . ?
C21 C26 1.4007(17) . ?
C22 C23 1.3812(19) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.3846(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.3942(17) . ?
C25 H25 0.9500 . ?
C27 C28 1.4919(17) . ?
C28 C33 1.3955(17) . ?
C28 C29 1.3965(17) . ?
C29 C30 1.3846(18) . ?
C29 H29 0.9500 . ?
C30 C31 1.385(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.383(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.3887(18) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
O10A C11A 1.247(3) . ?
N10A C11A 1.346(3) . ?
N10A C12A 1.448(2) . ?
N10A C13A 1.464(3) . ?
C10A C11A 1.492(3) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
O10B C11B 1.287(12) . ?
N10B C11B 1.315(17) . ?
N10B C12B 1.557(12) . ?
N10B C10B 1.586(13) . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B C13B 1.502(12) . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 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
C7 N1 C8 123.24(11) . . ?
C7 N1 H1N 119.6(11) . . ?
C8 N1 H1N 117.2(11) . . ?
C14 N2 C13 127.89(11) . . ?
C14 N2 H2N 114.1(12) . . ?
C13 N2 H2N 117.7(12) . . ?
C20 N3 C21 126.97(11) . . ?
C20 N3 H3N 115.3(11) . . ?
C21 N3 H3N 117.7(11) . . ?
C27 N4 C26 126.09(10) . . ?
C27 N4 H4N 115.5(10) . . ?
C26 N4 H4N 115.1(10) . . ?
C19 N5 C15 118.47(11) . . ?
C2 C1 C6 120.38(16) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 120.38(16) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 119.80(16) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.08(17) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.35(15) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.98(14) . . ?
C1 C6 C7 117.86(13) . . ?
C5 C6 C7 123.15(13) . . ?
O1 C7 N1 122.83(13) . . ?
O1 C7 C6 121.66(12) . . ?
N1 C7 C6 115.50(11) . . ?
C9 C8 C13 120.12(12) . . ?
C9 C8 N1 120.59(12) . . ?
C13 C8 N1 119.24(11) . . ?
C8 C9 C10 120.14(13) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.69(13) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 120.75(13) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.06(13) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 119.21(12) . . ?
C12 C13 N2 122.09(12) . . ?
C8 C13 N2 118.63(11) . . ?
O2 C14 N2 125.73(12) . . ?
O2 C14 C15 121.35(12) . . ?
N2 C14 C15 112.91(10) . . ?
N5 C15 C16 122.76(12) . . ?
N5 C15 C14 116.60(11) . . ?
C16 C15 C14 120.62(11) . . ?
C17 C16 C15 118.39(12) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C16 C17 C18 119.27(12) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 118.27(12) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
N5 C19 C18 122.84(11) . . ?
N5 C19 C20 116.66(11) . . ?
C18 C19 C20 120.50(11) . . ?
O3 C20 N3 126.05(11) . . ?
O3 C20 C19 120.93(11) . . ?
N3 C20 C19 113.02(10) . . ?
C22 C21 C26 119.09(11) . . ?
C22 C21 N3 120.09(11) . . ?
C26 C21 N3 120.80(11) . . ?
C23 C22 C21 121.06(12) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 120.03(12) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 119.40(12) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 121.25(12) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C21 119.07(11) . . ?
C25 C26 N4 117.14(11) . . ?
C21 C26 N4 123.66(11) . . ?
O4 C27 N4 122.29(11) . . ?
O4 C27 C28 120.84(11) . . ?
N4 C27 C28 116.87(10) . . ?
C33 C28 C29 119.15(11) . . ?
C33 C28 C27 123.26(11) . . ?
C29 C28 C27 117.58(11) . . ?
C30 C29 C28 120.24(12) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 120.26(12) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C32 C31 C30 119.97(12) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C33 120.20(12) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C28 120.18(12) . . ?
C32 C33 H33 119.9 . . ?
C28 C33 H33 119.9 . . ?
C11A N10A C12A 123.1(2) . . ?
C11A N10A C13A 117.22(19) . . ?
C12A N10A C13A 119.65(18) . . ?
C11A C10A H10A 109.5 . . ?
C11A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C11A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
O10A C11A N10A 119.9(2) . . ?
O10A C11A C10A 123.6(2) . . ?
N10A C11A C10A 116.4(2) . . ?
N10A C12A H12A 109.5 . . ?
N10A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
N10A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
N10A C13A H13A 109.5 . . ?
N10A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
N10A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C11B N10B C12B 118.9(11) . . ?
C11B N10B C10B 114.6(11) . . ?
C12B N10B C10B 126.2(8) . . ?
N10B C10B H10D 109.5 . . ?
N10B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
N10B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
O10B C11B N10B 109.5(12) . . ?
O10B C11B C13B 143.1(10) . . ?
N10B C11B C13B 107.4(11) . . ?
N10B C12B H12D 109.5 . . ?
N10B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
N10B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 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
C6 C1 C2 C3 1.4(3) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C2 C1 C6 C7 179.18(14) . . . . ?
C4 C5 C6 C1 -1.3(2) . . . . ?
C4 C5 C6 C7 179.80(15) . . . . ?
C8 N1 C7 O1 0.2(2) . . . . ?
C8 N1 C7 C6 178.81(12) . . . . ?
C1 C6 C7 O1 22.5(2) . . . . ?
C5 C6 C7 O1 -158.56(15) . . . . ?
C1 C6 C7 N1 -156.15(13) . . . . ?
C5 C6 C7 N1 22.8(2) . . . . ?
C7 N1 C8 C9 68.01(18) . . . . ?
C7 N1 C8 C13 -114.32(14) . . . . ?
C13 C8 C9 C10 1.4(2) . . . . ?
N1 C8 C9 C10 179.03(13) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
C11 C12 C13 C8 0.5(2) . . . . ?
C11 C12 C13 N2 -176.52(13) . . . . ?
C9 C8 C13 C12 -1.50(19) . . . . ?
N1 C8 C13 C12 -179.17(12) . . . . ?
C9 C8 C13 N2 175.58(12) . . . . ?
N1 C8 C13 N2 -2.09(18) . . . . ?
C14 N2 C13 C12 -24.3(2) . . . . ?
C14 N2 C13 C8 158.68(13) . . . . ?
C13 N2 C14 O2 -5.1(2) . . . . ?
C13 N2 C14 C15 173.61(12) . . . . ?
C19 N5 C15 C16 0.45(18) . . . . ?
C19 N5 C15 C14 -177.69(10) . . . . ?
O2 C14 C15 N5 171.96(12) . . . . ?
N2 C14 C15 N5 -6.78(16) . . . . ?
O2 C14 C15 C16 -6.22(19) . . . . ?
N2 C14 C15 C16 175.04(12) . . . . ?
N5 C15 C16 C17 -0.30(19) . . . . ?
C14 C15 C16 C17 177.77(12) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C16 C17 C18 C19 0.43(19) . . . . ?
C15 N5 C19 C18 -0.15(18) . . . . ?
C15 N5 C19 C20 179.52(10) . . . . ?
C17 C18 C19 N5 -0.29(19) . . . . ?
C17 C18 C19 C20 -179.94(11) . . . . ?
C21 N3 C20 O3 -6.0(2) . . . . ?
C21 N3 C20 C19 174.19(11) . . . . ?
N5 C19 C20 O3 171.46(11) . . . . ?
C18 C19 C20 O3 -8.87(18) . . . . ?
N5 C19 C20 N3 -8.69(15) . . . . ?
C18 C19 C20 N3 170.98(11) . . . . ?
C20 N3 C21 C22 -38.42(19) . . . . ?
C20 N3 C21 C26 142.77(13) . . . . ?
C26 C21 C22 C23 -2.98(19) . . . . ?
N3 C21 C22 C23 178.19(12) . . . . ?
C21 C22 C23 C24 0.5(2) . . . . ?
C22 C23 C24 C25 1.2(2) . . . . ?
C23 C24 C25 C26 -0.4(2) . . . . ?
C24 C25 C26 C21 -2.08(19) . . . . ?
C24 C25 C26 N4 -178.07(12) . . . . ?
C22 C21 C26 C25 3.73(18) . . . . ?
N3 C21 C26 C25 -177.46(11) . . . . ?
C22 C21 C26 N4 179.44(11) . . . . ?
N3 C21 C26 N4 -1.75(18) . . . . ?
C27 N4 C26 C25 -134.36(13) . . . . ?
C27 N4 C26 C21 49.85(18) . . . . ?
C26 N4 C27 O4 -4.12(19) . . . . ?
C26 N4 C27 C28 176.80(11) . . . . ?
O4 C27 C28 C33 -159.32(12) . . . . ?
N4 C27 C28 C33 19.78(17) . . . . ?
O4 C27 C28 C29 19.50(17) . . . . ?
N4 C27 C28 C29 -161.41(11) . . . . ?
C33 C28 C29 C30 -0.54(19) . . . . ?
C27 C28 C29 C30 -179.41(11) . . . . ?
C28 C29 C30 C31 0.7(2) . . . . ?
C29 C30 C31 C32 -0.4(2) . . . . ?
C30 C31 C32 C33 -0.1(2) . . . . ?
C31 C32 C33 C28 0.3(2) . . . . ?
C29 C28 C33 C32 0.01(19) . . . . ?
C27 C28 C33 C32 178.80(12) . . . . ?
C12A N10A C11A O10A 178.18(19) . . . . ?
C13A N10A C11A O10A 1.1(3) . . . . ?
C12A N10A C11A C10A 0.2(3) . . . . ?
C13A N10A C11A C10A -176.9(2) . . . . ?
C12B N10B C11B O10B -177.0(7) . . . . ?
C10B N10B C11B O10B -3.2(12) . . . . ?
C12B N10B C11B C13B 2.1(12) . . . . ?
C10B N10B C11B C13B 175.9(6) . . . . ?

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 O4 0.892(18) 2.037(18) 2.8676(14) 154.3(15) .
N2 H2N O4 0.842(18) 2.459(18) 3.1551(14) 140.5(15) .
N2 H2N N5 0.842(18) 2.175(18) 2.6424(15) 114.9(15) .
N3 H3N O4 0.876(17) 1.958(17) 2.6935(13) 140.7(15) .
N3 H3N N5 0.876(17) 2.184(16) 2.6429(14) 112.3(13) .
N4 H4N O3 0.885(17) 2.123(17) 2.9849(14) 164.4(15) 4_576

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.041

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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-DMSO-H2O-at
_database_code_depnum_ccdc_archive 'CCDC 1436661'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H25 N5 O4, C2 D6 O S, H2 O'
_chemical_formula_sum            'C35 H27 D6 N5 O6 S'
_chemical_formula_weight         657.76

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'
D D 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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.5114(7)
_cell_length_b                   19.1956(7)
_cell_length_c                   11.3102(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.975(4)
_cell_angle_gamma                90
_cell_volume                     3120.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2177
_cell_measurement_theta_min      3.8230
_cell_measurement_theta_max      75.3620

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.023
_shelx_estimated_absorpt_T_min   0.651
_shelx_estimated_absorpt_T_max   0.969
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 1 -7 0.1673 -1.0012 0.9992 -6.9989 -0.7842 0.5977 0.0493
2 11 -4 0.0946 1.9993 10.9988 -3.9993 -0.4312 0.2936 0.9075
-1 -6 6 0.1425 -0.9989 -5.9990 5.9991 0.6160 -0.5242 -0.4966
9 -4 -1 0.0098 8.9987 -3.9990 -1.0006 0.7062 0.7183 0.0148
-9 4 1 0.0131 -8.9987 3.9990 1.0006 -0.7062 -0.7183 -0.0148
-3 -12 0 0.0164 -3.0000 -11.9991 -0.0000 -0.0228 0.0527 -1.0133
3 12 0 0.0295 3.0000 11.9991 0.0000 0.0228 -0.0527 1.0133
1 -1 7 0.1655 1.0012 -0.9992 6.9989 0.7842 -0.5977 -0.0493
_exptl_absorpt_coefficient_mu    1.388
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_reflns_number            10673
_diffrn_reflns_av_unetI/netI     0.1141
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         76.915
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             6291
_reflns_number_gt                4046
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+0.4997P] 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         6291
_refine_ls_number_parameters     444
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1634
_refine_ls_wR_factor_gt          0.1416
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.094
_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 0.03971(19) 0.56853(14) 0.1383(2) 0.0286(6) Uani 1 1 d . . . . .
O2 O 0.42246(19) 0.61842(14) 0.3058(2) 0.0277(5) Uani 1 1 d . . . . .
O3 O 0.31222(18) 0.37506(13) 0.7302(2) 0.0239(5) Uani 1 1 d . . . . .
O4 O 0.25260(17) 0.37414(13) 0.2880(2) 0.0217(5) Uani 1 1 d . . . . .
N1 N 0.1430(2) 0.48013(16) 0.1679(2) 0.0218(6) Uani 1 1 d . . . . .
H1N H 0.162(3) 0.439(2) 0.208(4) 0.026 Uiso 1 1 d . U . . .
N2 N 0.3145(2) 0.53182(16) 0.2693(2) 0.0234(6) Uani 1 1 d . . . . .
H2N H 0.286(3) 0.493(2) 0.309(4) 0.028 Uiso 1 1 d . U . . .
N3 N 0.2724(2) 0.36582(15) 0.5270(2) 0.0193(6) Uani 1 1 d . . . . .
H3N H 0.275(3) 0.392(2) 0.460(4) 0.023 Uiso 1 1 d . U . . .
N4 N 0.2823(2) 0.26184(15) 0.3425(2) 0.0197(6) Uani 1 1 d . . . . .
H4N H 0.296(3) 0.221(2) 0.316(4) 0.024 Uiso 1 1 d . U . . .
N5 N 0.3470(2) 0.48858(15) 0.4929(2) 0.0202(6) Uani 1 1 d . . . . .
C1 C 0.0109(3) 0.4066(2) 0.2922(3) 0.0309(8) Uani 1 1 d . . . . .
H1A H 0.0510 0.3779 0.2538 0.037 Uiso 1 1 calc R U . . .
C2 C -0.0444(3) 0.3772(2) 0.3704(4) 0.0369(9) Uani 1 1 d . . . . .
H2 H -0.0426 0.3284 0.3843 0.044 Uiso 1 1 calc R U . . .
C3 C -0.1021(3) 0.4192(2) 0.4279(3) 0.0354(9) Uani 1 1 d . . . . .
H3 H -0.1399 0.3991 0.4812 0.042 Uiso 1 1 calc R U . . .
C4 C -0.1046(3) 0.4900(2) 0.4077(3) 0.0319(8) Uani 1 1 d . . . . .
H4A H -0.1437 0.5187 0.4479 0.038 Uiso 1 1 calc R U . . .
C5 C -0.0504(3) 0.5199(2) 0.3291(3) 0.0278(8) Uani 1 1 d . . . . .
H5 H -0.0525 0.5688 0.3154 0.033 Uiso 1 1 calc R U . . .
C6 C 0.0075(2) 0.47761(19) 0.2703(3) 0.0224(7) Uani 1 1 d . . . . .
C7 C 0.0635(2) 0.51293(19) 0.1866(3) 0.0213(7) Uani 1 1 d . . . . .
C8 C 0.2047(2) 0.50876(18) 0.0927(3) 0.0215(7) Uani 1 1 d . . . . .
C9 C 0.1805(3) 0.5084(2) -0.0304(3) 0.0255(7) Uani 1 1 d . . . . .
H9 H 0.1226 0.4891 -0.0648 0.031 Uiso 1 1 calc R U . . .
C10 C 0.2406(3) 0.5361(2) -0.1031(3) 0.0288(8) Uani 1 1 d . . . . .
H10 H 0.2242 0.5359 -0.1874 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3251(3) 0.5640(2) -0.0519(3) 0.0265(7) Uani 1 1 d . . . . .
H11 H 0.3659 0.5835 -0.1018 0.032 Uiso 1 1 calc R U . . .
C12 C 0.3508(3) 0.56387(19) 0.0706(3) 0.0243(7) Uani 1 1 d . . . . .
H12 H 0.4091 0.5827 0.1043 0.029 Uiso 1 1 calc R U . . .
C13 C 0.2902(2) 0.53581(19) 0.1446(3) 0.0215(7) Uani 1 1 d . . . . .
C14 C 0.3772(2) 0.57009(18) 0.3397(3) 0.0207(7) Uani 1 1 d . . . . .
C15 C 0.3892(2) 0.54760(18) 0.4689(3) 0.0202(6) Uani 1 1 d . . . . .
C16 C 0.4457(3) 0.58520(18) 0.5550(3) 0.0238(7) Uani 1 1 d . . . . .
H16 H 0.4752 0.6268 0.5346 0.029 Uiso 1 1 calc R U . . .
C17 C 0.4582(2) 0.56066(19) 0.6719(3) 0.0238(7) Uani 1 1 d . . . . .
H17 H 0.4957 0.5856 0.7333 0.029 Uiso 1 1 calc R U . . .
C18 C 0.4149(2) 0.49907(18) 0.6973(3) 0.0204(6) Uani 1 1 d . . . . .
H18 H 0.4230 0.4807 0.7760 0.024 Uiso 1 1 calc R U . . .
C19 C 0.3593(2) 0.46462(18) 0.6048(3) 0.0185(6) Uani 1 1 d . . . . .
C20 C 0.3119(2) 0.39704(18) 0.6278(3) 0.0186(6) Uani 1 1 d . . . . .
C21 C 0.2146(2) 0.30631(17) 0.5175(3) 0.0180(6) Uani 1 1 d . . . . .
C22 C 0.1493(2) 0.29721(19) 0.5968(3) 0.0211(7) Uani 1 1 d . . . . .
H22 H 0.1443 0.3316 0.6560 0.025 Uiso 1 1 calc R U . . .
C23 C 0.0922(2) 0.23959(19) 0.5909(3) 0.0234(7) Uani 1 1 d . . . . .
H23 H 0.0484 0.2343 0.6454 0.028 Uiso 1 1 calc R U . . .
C24 C 0.0992(2) 0.18896(19) 0.5038(3) 0.0234(7) Uani 1 1 d . . . . .
H24 H 0.0614 0.1484 0.4999 0.028 Uiso 1 1 calc R U . . .
C25 C 0.1618(2) 0.19840(19) 0.4231(3) 0.0227(7) Uani 1 1 d . . . . .
H25 H 0.1659 0.1642 0.3634 0.027 Uiso 1 1 calc R U . . .
C26 C 0.2185(2) 0.25692(18) 0.4278(3) 0.0185(6) Uani 1 1 d . . . . .
C27 C 0.2938(2) 0.31868(17) 0.2760(3) 0.0179(6) Uani 1 1 d . . . . .
C28 C 0.3621(2) 0.31283(18) 0.1890(3) 0.0195(6) Uani 1 1 d . . . . .
C29 C 0.3533(2) 0.36040(18) 0.0946(3) 0.0200(6) Uani 1 1 d . . . . .
H29 H 0.3042 0.3935 0.0869 0.024 Uiso 1 1 calc R U . . .
C30 C 0.4152(2) 0.35975(19) 0.0123(3) 0.0232(7) Uani 1 1 d . . . . .
H30 H 0.4083 0.3918 -0.0523 0.028 Uiso 1 1 calc R U . . .
C31 C 0.4879(2) 0.31186(19) 0.0246(3) 0.0241(7) Uani 1 1 d . . . . .
H31 H 0.5309 0.3115 -0.0316 0.029 Uiso 1 1 calc R U . . .
C32 C 0.4980(2) 0.26470(19) 0.1182(3) 0.0233(7) Uani 1 1 d . . . . .
H32 H 0.5481 0.2324 0.1266 0.028 Uiso 1 1 calc R U . . .
C33 C 0.4346(2) 0.26479(18) 0.2000(3) 0.0222(7) Uani 1 1 d . . . . .
H33 H 0.4409 0.2320 0.2635 0.027 Uiso 1 1 calc R U . . .
S100 S 0.73361(7) 0.24750(6) 0.50642(10) 0.0356(2) Uani 1 1 d . . . . .
O100 O 0.7589(2) 0.31536(16) 0.5683(3) 0.0382(7) Uani 1 1 d . . . . .
C100 C 0.7181(4) 0.2651(3) 0.3490(4) 0.0481(12) Uani 1 1 d . . . . .
D10A D 0.7742 0.2874 0.3277 0.072 Uiso 1 1 calc R U . . .
D10B D 0.6647 0.2961 0.3287 0.072 Uiso 1 1 calc R U . . .
D10C D 0.7071 0.2213 0.3049 0.072 Uiso 1 1 calc R U . . .
C101 C 0.8384(3) 0.1987(2) 0.5127(4) 0.0352(9) Uani 1 1 d . . . . .
D10D D 0.8266 0.1561 0.4652 0.053 Uiso 1 1 calc R U . . .
D10E D 0.8608 0.1863 0.5959 0.053 Uiso 1 1 calc R U . . .
D10F D 0.8857 0.2267 0.4806 0.053 Uiso 1 1 calc R U . . .
O200 O 0.0780(3) 0.70114(19) 0.2586(3) 0.0477(8) Uani 1 1 d D . . . .
H1O H 0.127(3) 0.691(3) 0.306(5) 0.057 Uiso 1 1 d D U . . .
H2O H 0.062(4) 0.6630(19) 0.221(5) 0.057 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.227(4) . ?
O2 C14 1.229(4) . ?
O3 C20 1.233(4) . ?
O4 C27 1.238(4) . ?
N1 C7 1.355(5) . ?
N1 C8 1.428(4) . ?
N1 H1N 0.94(5) . ?
N2 C14 1.342(5) . ?
N2 C13 1.409(4) . ?
N2 H2N 0.99(5) . ?
N3 C20 1.344(4) . ?
N3 C21 1.412(4) . ?
N3 H3N 0.91(5) . ?
N4 C27 1.349(4) . ?
N4 C26 1.429(4) . ?
N4 H4N 0.88(5) . ?
N5 C15 1.334(5) . ?
N5 C19 1.335(4) . ?
C1 C6 1.384(5) . ?
C1 C2 1.393(6) . ?
C1 H1A 0.9500 . ?
C2 C3 1.388(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.402(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.493(5) . ?
C8 C9 1.388(5) . ?
C8 C13 1.396(5) . ?
C9 C10 1.386(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(5) . ?
C12 H12 0.9500 . ?
C14 C15 1.510(4) . ?
C15 C16 1.385(5) . ?
C16 C17 1.392(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.396(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.508(5) . ?
C21 C26 1.395(5) . ?
C21 C22 1.404(5) . ?
C22 C23 1.378(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.398(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(5) . ?
C25 H25 0.9500 . ?
C27 C28 1.495(5) . ?
C28 C33 1.392(5) . ?
C28 C29 1.398(5) . ?
C29 C30 1.380(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.391(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.385(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.393(5) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
S100 O100 1.500(3) . ?
S100 C101 1.780(4) . ?
S100 C100 1.795(5) . ?
C100 D10A 0.9800 . ?
C100 D10B 0.9800 . ?
C100 D10C 0.9800 . ?
C101 D10D 0.9800 . ?
C101 D10E 0.9800 . ?
C101 D10F 0.9800 . ?
O200 H1O 0.85(2) . ?
O200 H2O 0.86(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 122.1(3) . . ?
C7 N1 H1N 121(3) . . ?
C8 N1 H1N 117(3) . . ?
C14 N2 C13 128.3(3) . . ?
C14 N2 H2N 116(3) . . ?
C13 N2 H2N 115(3) . . ?
C20 N3 C21 127.2(3) . . ?
C20 N3 H3N 114(3) . . ?
C21 N3 H3N 118(3) . . ?
C27 N4 C26 124.9(3) . . ?
C27 N4 H4N 119(3) . . ?
C26 N4 H4N 111(3) . . ?
C15 N5 C19 118.7(3) . . ?
C6 C1 C2 120.2(4) . . ?
C6 C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C6 119.6(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 C7 123.5(3) . . ?
C5 C6 C7 116.9(3) . . ?
O1 C7 N1 121.9(3) . . ?
O1 C7 C6 122.2(3) . . ?
N1 C7 C6 115.9(3) . . ?
C9 C8 C13 120.7(3) . . ?
C9 C8 N1 120.2(3) . . ?
C13 C8 N1 119.1(3) . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 119.1(3) . . ?
C8 C13 N2 119.0(3) . . ?
C12 C13 N2 121.8(3) . . ?
O2 C14 N2 125.2(3) . . ?
O2 C14 C15 121.6(3) . . ?
N2 C14 C15 113.3(3) . . ?
N5 C15 C16 122.9(3) . . ?
N5 C15 C14 116.4(3) . . ?
C16 C15 C14 120.6(3) . . ?
C15 C16 C17 118.6(3) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C18 C17 C16 118.8(3) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 C19 118.7(3) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
N5 C19 C18 122.3(3) . . ?
N5 C19 C20 117.1(3) . . ?
C18 C19 C20 120.5(3) . . ?
O3 C20 N3 126.2(3) . . ?
O3 C20 C19 121.0(3) . . ?
N3 C20 C19 112.9(3) . . ?
C26 C21 C22 118.6(3) . . ?
C26 C21 N3 121.5(3) . . ?
C22 C21 N3 119.9(3) . . ?
C23 C22 C21 121.6(3) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C24 119.4(3) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 119.5(3) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 121.3(3) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C21 119.6(3) . . ?
C25 C26 N4 117.6(3) . . ?
C21 C26 N4 122.7(3) . . ?
O4 C27 N4 122.4(3) . . ?
O4 C27 C28 120.8(3) . . ?
N4 C27 C28 116.8(3) . . ?
C33 C28 C29 119.3(3) . . ?
C33 C28 C27 123.6(3) . . ?
C29 C28 C27 117.1(3) . . ?
C30 C29 C28 120.7(3) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 119.6(3) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C32 C31 C30 120.4(3) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C31 C32 C33 119.8(3) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C28 C33 C32 120.2(3) . . ?
C28 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
O100 S100 C101 106.62(19) . . ?
O100 S100 C100 106.8(2) . . ?
C101 S100 C100 97.3(2) . . ?
S100 C100 D10A 109.5 . . ?
S100 C100 D10B 109.5 . . ?
D10A C100 D10B 109.5 . . ?
S100 C100 D10C 109.5 . . ?
D10A C100 D10C 109.5 . . ?
D10B C100 D10C 109.5 . . ?
S100 C101 D10D 109.5 . . ?
S100 C101 D10E 109.5 . . ?
D10D C101 D10E 109.5 . . ?
S100 C101 D10F 109.5 . . ?
D10D C101 D10F 109.5 . . ?
D10E C101 D10F 109.5 . . ?
H1O O200 H2O 105(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
C6 C1 C2 C3 -0.9(6) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C2 C1 C6 C5 1.4(6) . . . . ?
C2 C1 C6 C7 -179.2(3) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C4 C5 C6 C7 179.7(3) . . . . ?
C8 N1 C7 O1 1.2(5) . . . . ?
C8 N1 C7 C6 -178.3(3) . . . . ?
C1 C6 C7 O1 155.6(4) . . . . ?
C5 C6 C7 O1 -24.9(5) . . . . ?
C1 C6 C7 N1 -25.0(5) . . . . ?
C5 C6 C7 N1 154.5(3) . . . . ?
C7 N1 C8 C9 -73.2(5) . . . . ?
C7 N1 C8 C13 108.0(4) . . . . ?
C13 C8 C9 C10 -1.1(6) . . . . ?
N1 C8 C9 C10 -179.9(3) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C10 C11 C12 C13 -0.8(6) . . . . ?
C9 C8 C13 C12 1.1(6) . . . . ?
N1 C8 C13 C12 179.9(3) . . . . ?
C9 C8 C13 N2 -176.5(3) . . . . ?
N1 C8 C13 N2 2.3(5) . . . . ?
C11 C12 C13 C8 -0.2(6) . . . . ?
C11 C12 C13 N2 177.4(4) . . . . ?
C14 N2 C13 C8 -159.3(4) . . . . ?
C14 N2 C13 C12 23.1(6) . . . . ?
C13 N2 C14 O2 3.2(6) . . . . ?
C13 N2 C14 C15 -176.0(3) . . . . ?
C19 N5 C15 C16 0.2(5) . . . . ?
C19 N5 C15 C14 176.7(3) . . . . ?
O2 C14 C15 N5 -170.5(3) . . . . ?
N2 C14 C15 N5 8.7(5) . . . . ?
O2 C14 C15 C16 6.0(5) . . . . ?
N2 C14 C15 C16 -174.7(3) . . . . ?
N5 C15 C16 C17 -0.7(6) . . . . ?
C14 C15 C16 C17 -177.0(3) . . . . ?
C15 C16 C17 C18 1.0(6) . . . . ?
C16 C17 C18 C19 -1.0(5) . . . . ?
C15 N5 C19 C18 -0.1(5) . . . . ?
C15 N5 C19 C20 -178.8(3) . . . . ?
C17 C18 C19 N5 0.5(5) . . . . ?
C17 C18 C19 C20 179.2(3) . . . . ?
C21 N3 C20 O3 7.8(6) . . . . ?
C21 N3 C20 C19 -172.7(3) . . . . ?
N5 C19 C20 O3 -172.7(3) . . . . ?
C18 C19 C20 O3 8.5(5) . . . . ?
N5 C19 C20 N3 7.8(4) . . . . ?
C18 C19 C20 N3 -171.0(3) . . . . ?
C20 N3 C21 C26 -143.9(3) . . . . ?
C20 N3 C21 C22 38.4(5) . . . . ?
C26 C21 C22 C23 2.7(5) . . . . ?
N3 C21 C22 C23 -179.5(3) . . . . ?
C21 C22 C23 C24 -0.1(5) . . . . ?
C22 C23 C24 C25 -1.6(5) . . . . ?
C23 C24 C25 C26 0.7(5) . . . . ?
C24 C25 C26 C21 1.9(5) . . . . ?
C24 C25 C26 N4 178.9(3) . . . . ?
C22 C21 C26 C25 -3.5(5) . . . . ?
N3 C21 C26 C25 178.7(3) . . . . ?
C22 C21 C26 N4 179.7(3) . . . . ?
N3 C21 C26 N4 1.9(5) . . . . ?
C27 N4 C26 C25 132.0(3) . . . . ?
C27 N4 C26 C21 -51.2(5) . . . . ?
C26 N4 C27 O4 4.1(5) . . . . ?
C26 N4 C27 C28 -178.2(3) . . . . ?
O4 C27 C28 C33 154.9(3) . . . . ?
N4 C27 C28 C33 -22.9(5) . . . . ?
O4 C27 C28 C29 -22.8(4) . . . . ?
N4 C27 C28 C29 159.5(3) . . . . ?
C33 C28 C29 C30 0.4(5) . . . . ?
C27 C28 C29 C30 178.2(3) . . . . ?
C28 C29 C30 C31 -0.9(5) . . . . ?
C29 C30 C31 C32 0.4(5) . . . . ?
C30 C31 C32 C33 0.5(5) . . . . ?
C29 C28 C33 C32 0.5(5) . . . . ?
C27 C28 C33 C32 -177.0(3) . . . . ?
C31 C32 C33 C28 -1.0(5) . . . . ?

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 O4 0.94(5) 1.94(5) 2.813(4) 154(4) .
N2 H2N O4 0.99(5) 2.33(5) 3.173(4) 142(4) .
N3 H3N O4 0.91(5) 1.95(4) 2.684(3) 136(4) .
N3 H3N N5 0.91(5) 2.14(4) 2.644(4) 114(3) .
N4 H4N O3 0.88(5) 2.11(5) 2.977(4) 171(4) 4_565
O200 H1O O100 0.85(2) 2.03(2) 2.872(5) 169(6) 3_666
O200 H2O O1 0.86(2) 2.04(2) 2.903(4) 173(6) .

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.067

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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-MeCN-at
_database_code_depnum_ccdc_archive 'CCDC 1436662'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H25 N5 O4, C2 H3 N'
_chemical_formula_sum            'C35 H28 N6 O4'
_chemical_formula_weight         596.63

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

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

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

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

_cell_length_a                   13.934(3)
_cell_length_b                   19.1670(19)
_cell_length_c                   11.1543(14)
_cell_angle_alpha                90
_cell_angle_beta                 94.855(18)
_cell_angle_gamma                90
_cell_volume                     2968.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.730
_shelx_estimated_absorpt_T_min   0.769
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13229
_diffrn_reflns_av_unetI/netI     0.1142
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.183
_diffrn_reflns_theta_max         71.997
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5828
_reflns_number_gt                3507
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)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         5828
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1499
_refine_ls_wR_factor_gt          0.1209
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_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
O2 O 0.79854(16) 0.62686(10) 0.74487(17) 0.0310(5) Uani 1 1 d . . . . .
O1 O 0.73692(16) 0.62440(10) 0.30070(16) 0.0288(5) Uani 1 1 d . . . . .
N2 N 0.75597(19) 0.63534(12) 0.5422(2) 0.0276(5) Uani 1 1 d . . . . .
O3 O 0.91671(18) 0.38302(10) 0.30980(18) 0.0370(5) Uani 1 1 d . . . . .
N5 N 0.84674(18) 0.51849(12) 0.4997(2) 0.0271(5) Uani 1 1 d . . . . .
N1 N 0.7650(2) 0.73707(12) 0.3537(2) 0.0284(5) Uani 1 1 d . . . . .
O4 O 0.51511(19) 0.42416(11) 0.1927(2) 0.0416(6) Uani 1 1 d . . . . .
N3 N 0.8170(2) 0.47649(13) 0.2718(2) 0.0302(6) Uani 1 1 d . . . . .
C7 C 0.7799(2) 0.68033(14) 0.2872(2) 0.0271(6) Uani 1 1 d . . . . .
C6 C 0.8525(2) 0.68629(14) 0.1961(2) 0.0259(6) Uani 1 1 d . . . . .
C12 C 0.6259(2) 0.70208(14) 0.6189(2) 0.0289(6) Uani 1 1 d . . . . .
H12 H 0.6212 0.6683 0.6804 0.035 Uiso 1 1 calc R U . . .
C13 C 0.6938(2) 0.69374(14) 0.5356(2) 0.0268(6) Uani 1 1 d . . . . .
C1 C 0.9281(2) 0.73411(15) 0.2073(3) 0.0307(7) Uani 1 1 d . . . . .
H1A H 0.9341 0.7656 0.2733 0.037 Uiso 1 1 calc R U . . .
C5 C 0.8447(2) 0.63970(14) 0.0999(2) 0.0280(6) Uani 1 1 d . . . . .
H5 H 0.7941 0.6064 0.0931 0.034 Uiso 1 1 calc R U . . .
C9 C 0.6375(2) 0.80051(14) 0.4398(2) 0.0292(6) Uani 1 1 d . . . . .
H9 H 0.6417 0.8345 0.3784 0.035 Uiso 1 1 calc R U . . .
C14 C 0.8003(2) 0.60511(14) 0.6412(2) 0.0274(6) Uani 1 1 d . . . . .
C15 C 0.8529(2) 0.53941(14) 0.6146(2) 0.0255(6) Uani 1 1 d . . . . .
C20 C 0.8768(2) 0.43496(15) 0.3429(3) 0.0292(6) Uani 1 1 d . . . . .
C16 C 0.9026(2) 0.50114(15) 0.7064(2) 0.0305(7) Uani 1 1 d . . . . .
H16 H 0.9064 0.5174 0.7871 0.037 Uiso 1 1 calc R U . . .
N4 N 0.6272(2) 0.51031(13) 0.1916(2) 0.0306(6) Uani 1 1 d . . . . .
C8 C 0.6977(2) 0.74219(14) 0.4431(2) 0.0266(6) Uani 1 1 d . . . . .
C4 C 0.9110(2) 0.64205(15) 0.0143(2) 0.0307(7) Uani 1 1 d . . . . .
H4A H 0.9053 0.6108 -0.0520 0.037 Uiso 1 1 calc R U . . .
C21 C 0.7825(2) 0.46104(14) 0.1508(2) 0.0289(6) Uani 1 1 d . . . . .
C26 C 0.6875(2) 0.47734(14) 0.1121(3) 0.0302(7) Uani 1 1 d . . . . .
C11 C 0.5645(2) 0.76001(15) 0.6128(3) 0.0335(7) Uani 1 1 d . . . . .
H11 H 0.5178 0.7651 0.6695 0.040 Uiso 1 1 calc R U . . .
C18 C 0.9390(2) 0.41688(15) 0.5586(3) 0.0318(7) Uani 1 1 d . . . . .
H18 H 0.9676 0.3742 0.5366 0.038 Uiso 1 1 calc R U . . .
C27 C 0.5439(2) 0.48199(15) 0.2240(3) 0.0313(7) Uani 1 1 d . . . . .
C10 C 0.5717(2) 0.80953(15) 0.5247(2) 0.0331(7) Uani 1 1 d . . . . .
H10 H 0.5317 0.8497 0.5222 0.040 Uiso 1 1 calc R U . . .
C28 C 0.4887(2) 0.52725(15) 0.3047(2) 0.0292(6) Uani 1 1 d . . . . .
C2 C 0.9948(2) 0.73551(15) 0.1215(3) 0.0332(7) Uani 1 1 d . . . . .
H2A H 1.0466 0.7678 0.1290 0.040 Uiso 1 1 calc R U . . .
C22 C 0.8425(2) 0.43148(16) 0.0722(3) 0.0335(7) Uani 1 1 d . . . . .
H22 H 0.9080 0.4221 0.0978 0.040 Uiso 1 1 calc R U . . .
C3 C 0.9859(2) 0.69003(15) 0.0252(3) 0.0323(7) Uani 1 1 d . . . . .
H3A H 1.0311 0.6916 -0.0338 0.039 Uiso 1 1 calc R U . . .
C19 C 0.8892(2) 0.45857(14) 0.4728(2) 0.0276(6) Uani 1 1 d . . . . .
C23 C 0.8062(3) 0.41567(16) -0.0449(3) 0.0369(8) Uani 1 1 d . . . . .
H23 H 0.8467 0.3939 -0.0982 0.044 Uiso 1 1 calc R U . . .
C17 C 0.9462(2) 0.43917(15) 0.6779(3) 0.0321(7) Uani 1 1 d . . . . .
H17 H 0.9806 0.4122 0.7388 0.039 Uiso 1 1 calc R U . . .
C24 C 0.7121(3) 0.43128(18) -0.0840(3) 0.0431(8) Uani 1 1 d . . . . .
H24 H 0.6880 0.4209 -0.1643 0.052 Uiso 1 1 calc R U . . .
C25 C 0.6530(3) 0.46220(17) -0.0058(3) 0.0399(8) Uani 1 1 d . . . . .
H25 H 0.5883 0.4732 -0.0327 0.048 Uiso 1 1 calc R U . . .
C31 C 0.3871(3) 0.60572(19) 0.4613(3) 0.0413(8) Uani 1 1 d . . . . .
H31 H 0.3524 0.6324 0.5149 0.050 Uiso 1 1 calc R U . . .
C30 C 0.4522(2) 0.63839(16) 0.3924(3) 0.0367(7) Uani 1 1 d . . . . .
H30 H 0.4617 0.6874 0.3983 0.044 Uiso 1 1 calc R U . . .
C29 C 0.5033(2) 0.59906(16) 0.3147(3) 0.0325(7) Uani 1 1 d . . . . .
H29 H 0.5485 0.6212 0.2681 0.039 Uiso 1 1 calc R U . . .
C33 C 0.4228(2) 0.49594(17) 0.3734(3) 0.0351(7) Uani 1 1 d . . . . .
H33 H 0.4117 0.4471 0.3665 0.042 Uiso 1 1 calc R U . . .
C32 C 0.3727(2) 0.53490(18) 0.4522(3) 0.0396(8) Uani 1 1 d . . . . .
H32 H 0.3284 0.5127 0.4999 0.047 Uiso 1 1 calc R U . . .
N100 N 0.7978(4) 0.2665(2) 0.5535(5) 0.0884(15) Uani 1 1 d . . . . .
C101 C 0.7601(4) 0.2444(2) 0.6324(5) 0.0665(13) Uani 1 1 d . . . . .
C100 C 0.7122(4) 0.2163(2) 0.7331(5) 0.0721(13) Uani 1 1 d . . . . .
H10A H 0.7584 0.1890 0.7851 0.108 Uiso 1 1 calc R U . . .
H10B H 0.6588 0.1862 0.7026 0.108 Uiso 1 1 calc R U . . .
H10C H 0.6873 0.2547 0.7794 0.108 Uiso 1 1 calc R U . . .
H1 H 0.787(4) 0.777(3) 0.330(5) 0.087 Uiso 1 1 d . U . . .
H3 H 0.787(4) 0.516(2) 0.306(5) 0.087 Uiso 1 1 d . U . . .
H4 H 0.647(4) 0.553(2) 0.230(5) 0.087 Uiso 1 1 d . U . . .
H2 H 0.760(3) 0.611(2) 0.472(5) 0.087 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C14 1.232(3) . ?
O1 C7 1.243(4) . ?
N2 C14 1.349(4) . ?
N2 C13 1.413(4) . ?
N2 H2 0.92(5) . ?
O3 C20 1.213(4) . ?
N5 C19 1.337(4) . ?
N5 C15 1.339(4) . ?
N1 C7 1.343(4) . ?
N1 C8 1.428(4) . ?
N1 H1 0.86(5) . ?
O4 C27 1.220(4) . ?
N3 C20 1.359(4) . ?
N3 C21 1.424(4) . ?
N3 H3 0.96(5) . ?
C7 C6 1.498(4) . ?
C6 C5 1.393(4) . ?
C6 C1 1.394(4) . ?
C12 C13 1.390(4) . ?
C12 C11 1.400(4) . ?
C12 H12 0.9500 . ?
C13 C8 1.393(4) . ?
C1 C2 1.390(4) . ?
C1 H1A 0.9500 . ?
C5 C4 1.385(4) . ?
C5 H5 0.9500 . ?
C9 C10 1.383(4) . ?
C9 C8 1.397(4) . ?
C9 H9 0.9500 . ?
C14 C15 1.500(4) . ?
C15 C16 1.395(4) . ?
C20 C19 1.514(4) . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
N4 C27 1.358(4) . ?
N4 C26 1.421(4) . ?
N4 H4 0.96(5) . ?
C4 C3 1.388(5) . ?
C4 H4A 0.9500 . ?
C21 C22 1.384(4) . ?
C21 C26 1.392(5) . ?
C26 C25 1.392(4) . ?
C11 C10 1.376(4) . ?
C11 H11 0.9500 . ?
C18 C19 1.387(4) . ?
C18 C17 1.393(4) . ?
C18 H18 0.9500 . ?
C27 C28 1.507(4) . ?
C10 H10 0.9500 . ?
C28 C33 1.381(4) . ?
C28 C29 1.394(4) . ?
C2 C3 1.381(4) . ?
C2 H2A 0.9500 . ?
C22 C23 1.393(4) . ?
C22 H22 0.9500 . ?
C3 H3A 0.9500 . ?
C23 C24 1.380(5) . ?
C23 H23 0.9500 . ?
C17 H17 0.9500 . ?
C24 C25 1.383(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C31 C32 1.375(5) . ?
C31 C30 1.386(5) . ?
C31 H31 0.9500 . ?
C30 C29 1.390(4) . ?
C30 H30 0.9500 . ?
C29 H29 0.9500 . ?
C33 C32 1.386(4) . ?
C33 H33 0.9500 . ?
C32 H32 0.9500 . ?
N100 C101 1.144(6) . ?
C101 C100 1.458(6) . ?
C100 H10A 0.9800 . ?
C100 H10B 0.9800 . ?
C100 H10C 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
C14 N2 C13 128.3(2) . . ?
C14 N2 H2 115(3) . . ?
C13 N2 H2 116(3) . . ?
C19 N5 C15 118.5(2) . . ?
C7 N1 C8 125.6(3) . . ?
C7 N1 H1 118(3) . . ?
C8 N1 H1 115(3) . . ?
C20 N3 C21 124.9(2) . . ?
C20 N3 H3 120(3) . . ?
C21 N3 H3 115(3) . . ?
O1 C7 N1 122.2(3) . . ?
O1 C7 C6 120.5(3) . . ?
N1 C7 C6 117.2(3) . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 C7 117.4(3) . . ?
C1 C6 C7 122.6(2) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 119.4(3) . . ?
C12 C13 N2 120.3(3) . . ?
C8 C13 N2 120.3(3) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 H1A 120.2 . . ?
C6 C1 H1A 120.2 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
O2 C14 N2 125.4(3) . . ?
O2 C14 C15 121.2(3) . . ?
N2 C14 C15 113.4(2) . . ?
N5 C15 C16 122.2(3) . . ?
N5 C15 C14 116.6(2) . . ?
C16 C15 C14 121.1(2) . . ?
O3 C20 N3 125.3(3) . . ?
O3 C20 C19 121.3(3) . . ?
N3 C20 C19 113.4(2) . . ?
C17 C16 C15 118.9(3) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C27 N4 C26 123.5(2) . . ?
C27 N4 H4 117(3) . . ?
C26 N4 H4 120(3) . . ?
C13 C8 C9 119.5(3) . . ?
C13 C8 N1 122.7(3) . . ?
C9 C8 N1 117.7(2) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C22 C21 C26 120.3(3) . . ?
C22 C21 N3 120.8(3) . . ?
C26 C21 N3 118.9(3) . . ?
C25 C26 C21 119.3(3) . . ?
C25 C26 N4 120.5(3) . . ?
C21 C26 N4 120.2(3) . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C19 C18 C17 118.3(3) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
O4 C27 N4 123.7(3) . . ?
O4 C27 C28 121.5(3) . . ?
N4 C27 C28 114.8(3) . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C33 C28 C29 119.0(3) . . ?
C33 C28 C27 118.5(3) . . ?
C29 C28 C27 122.5(3) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C21 C22 C23 119.5(3) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
N5 C19 C18 123.1(3) . . ?
N5 C19 C20 117.0(3) . . ?
C18 C19 C20 119.8(3) . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C16 C17 C18 119.0(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C23 C24 C25 119.6(3) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 120.6(3) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C32 C31 C30 120.2(3) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C30 C29 119.6(3) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C30 C29 C28 120.4(3) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C28 C33 C32 120.8(3) . . ?
C28 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C31 C32 C33 120.0(3) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
N100 C101 C100 179.8(8) . . ?
C101 C100 H10A 109.5 . . ?
C101 C100 H10B 109.5 . . ?
H10A C100 H10B 109.5 . . ?
C101 C100 H10C 109.5 . . ?
H10A C100 H10C 109.5 . . ?
H10B C100 H10C 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
C8 N1 C7 O1 -2.4(4) . . . . ?
C8 N1 C7 C6 178.7(3) . . . . ?
O1 C7 C6 C5 23.7(4) . . . . ?
N1 C7 C6 C5 -157.4(3) . . . . ?
O1 C7 C6 C1 -153.7(3) . . . . ?
N1 C7 C6 C1 25.2(4) . . . . ?
C11 C12 C13 C8 -2.5(4) . . . . ?
C11 C12 C13 N2 179.8(3) . . . . ?
C14 N2 C13 C12 -40.0(5) . . . . ?
C14 N2 C13 C8 142.3(3) . . . . ?
C5 C6 C1 C2 0.7(4) . . . . ?
C7 C6 C1 C2 178.0(3) . . . . ?
C1 C6 C5 C4 -1.4(4) . . . . ?
C7 C6 C5 C4 -178.8(3) . . . . ?
C13 N2 C14 O2 -5.0(5) . . . . ?
C13 N2 C14 C15 174.0(3) . . . . ?
C19 N5 C15 C16 0.5(4) . . . . ?
C19 N5 C15 C14 -177.2(3) . . . . ?
O2 C14 C15 N5 177.0(3) . . . . ?
N2 C14 C15 N5 -2.1(4) . . . . ?
O2 C14 C15 C16 -0.7(5) . . . . ?
N2 C14 C15 C16 -179.8(3) . . . . ?
C21 N3 C20 O3 7.9(5) . . . . ?
C21 N3 C20 C19 -170.9(3) . . . . ?
N5 C15 C16 C17 -0.6(5) . . . . ?
C14 C15 C16 C17 177.0(3) . . . . ?
C12 C13 C8 C9 3.9(4) . . . . ?
N2 C13 C8 C9 -178.3(3) . . . . ?
C12 C13 C8 N1 -179.7(3) . . . . ?
N2 C13 C8 N1 -1.9(4) . . . . ?
C10 C9 C8 C13 -2.3(4) . . . . ?
C10 C9 C8 N1 -178.9(3) . . . . ?
C7 N1 C8 C13 51.3(4) . . . . ?
C7 N1 C8 C9 -132.2(3) . . . . ?
C6 C5 C4 C3 0.9(4) . . . . ?
C20 N3 C21 C22 -40.3(5) . . . . ?
C20 N3 C21 C26 140.8(3) . . . . ?
C22 C21 C26 C25 1.4(4) . . . . ?
N3 C21 C26 C25 -179.7(3) . . . . ?
C22 C21 C26 N4 -177.4(3) . . . . ?
N3 C21 C26 N4 1.5(4) . . . . ?
C27 N4 C26 C25 61.1(4) . . . . ?
C27 N4 C26 C21 -120.1(3) . . . . ?
C13 C12 C11 C10 -0.7(5) . . . . ?
C26 N4 C27 O4 3.7(5) . . . . ?
C26 N4 C27 C28 -177.3(3) . . . . ?
C12 C11 C10 C9 2.3(5) . . . . ?
C8 C9 C10 C11 -0.9(5) . . . . ?
O4 C27 C28 C33 20.2(4) . . . . ?
N4 C27 C28 C33 -158.9(3) . . . . ?
O4 C27 C28 C29 -161.3(3) . . . . ?
N4 C27 C28 C29 19.6(4) . . . . ?
C6 C1 C2 C3 0.3(5) . . . . ?
C26 C21 C22 C23 -2.5(5) . . . . ?
N3 C21 C22 C23 178.7(3) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C5 C4 C3 C2 0.2(4) . . . . ?
C15 N5 C19 C18 0.2(4) . . . . ?
C15 N5 C19 C20 177.3(3) . . . . ?
C17 C18 C19 N5 -0.9(5) . . . . ?
C17 C18 C19 C20 -177.9(3) . . . . ?
O3 C20 C19 N5 176.4(3) . . . . ?
N3 C20 C19 N5 -4.7(4) . . . . ?
O3 C20 C19 C18 -6.4(5) . . . . ?
N3 C20 C19 C18 172.5(3) . . . . ?
C21 C22 C23 C24 2.1(5) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C19 C18 C17 C16 0.8(5) . . . . ?
C22 C23 C24 C25 -0.8(5) . . . . ?
C23 C24 C25 C26 -0.3(5) . . . . ?
C21 C26 C25 C24 0.0(5) . . . . ?
N4 C26 C25 C24 178.8(3) . . . . ?
C32 C31 C30 C29 -0.4(5) . . . . ?
C31 C30 C29 C28 0.7(5) . . . . ?
C33 C28 C29 C30 -0.1(5) . . . . ?
C27 C28 C29 C30 -178.5(3) . . . . ?
C29 C28 C33 C32 -0.8(5) . . . . ?
C27 C28 C33 C32 177.7(3) . . . . ?
C30 C31 C32 C33 -0.4(5) . . . . ?
C28 C33 C32 C31 1.1(5) . . . . ?

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 H1 O2 0.86(5) 2.10(5) 2.931(3) 163(5) 4_575
N3 H3 O1 0.96(5) 2.19(5) 3.073(3) 152(4) .
N4 H4 O1 0.96(5) 1.97(5) 2.878(3) 158(4) .
N2 H2 O1 0.92(5) 1.93(5) 2.693(3) 139(4) .
N2 H2 N5 0.92(5) 2.15(5) 2.635(3) 112(4) .

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.060

_shelxl_version_number           2014/6

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

data_2-DCM-1-S1
_database_code_depnum_ccdc_archive 'CCDC 1436663'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 N4 O3, C H2 Cl2'
_chemical_formula_sum            'C27 H22 Cl2 N4 O3'
_chemical_formula_weight         521.39

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'
Cl Cl 0.3639 0.7018 '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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9343(2)
_cell_length_b                   12.0833(2)
_cell_length_c                   13.1298(2)
_cell_angle_alpha                112.097(2)
_cell_angle_beta                 93.024(2)
_cell_angle_gamma                101.520(2)
_cell_volume                     1274.04(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540
_exptl_absorpt_coefficient_mu    2.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4725
_exptl_absorpt_correction_T_max  0.7814
_exptl_absorpt_process_details   
;
Denzo (otwinowski, Borek, Majewski & Minor, 2003) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KappaCCD, Cu, APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5929
_diffrn_reflns_av_R_equivalents  0.0863
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.67
_diffrn_reflns_theta_max         66.68
_reflns_number_total             4297
_reflns_number_gt                3295
_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)+(0.0883P)²+0.9735P] 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         4297
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1830
_refine_ls_wR_factor_gt          0.1671
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4580(2) 0.31247(18) 0.11885(17) 0.0425(5) Uani 1 1 d . . .
O2 O 0.4699(2) 0.75837(18) 0.28142(16) 0.0419(5) Uani 1 1 d . . .
O3 O 0.1937(2) 1.0159(2) -0.06716(18) 0.0485(6) Uani 1 1 d . . .
N1 N 0.4862(3) 0.5192(2) 0.1778(2) 0.0385(6) Uani 1 1 d . . .
H1N H 0.453(4) 0.585(3) 0.219(3) 0.046 Uiso 1 1 d . . .
N2 N 0.5372(3) 0.7188(2) 0.1085(2) 0.0359(5) Uani 1 1 d . . .
H2N H 0.519(4) 0.731(3) 0.043(3) 0.043 Uiso 1 1 d . . .
N3 N 0.3512(3) 0.8831(2) -0.1252(2) 0.0386(6) Uani 1 1 d . . .
H3N H 0.390(4) 0.835(3) -0.104(3) 0.046 Uiso 1 1 d . . .
N4 N 0.3547(3) 0.8566(2) 0.07201(19) 0.0342(5) Uani 1 1 d . . .
C1 C 0.2394(4) 0.5046(3) 0.3062(3) 0.0479(8) Uani 1 1 d . . .
H1 H 0.3085 0.5829 0.3281 0.057 Uiso 1 1 calc R . .
C2 C 0.1050(4) 0.4930(4) 0.3537(3) 0.0581(9) Uani 1 1 d . . .
H2 H 0.0808 0.5636 0.4068 0.070 Uiso 1 1 calc R . .
C3 C 0.0069(4) 0.3789(4) 0.3235(3) 0.0565(9) Uani 1 1 d . . .
H3 H -0.0845 0.3708 0.3566 0.068 Uiso 1 1 calc R . .
C4 C 0.0403(4) 0.2767(4) 0.2460(3) 0.0590(9) Uani 1 1 d . . .
H4 H -0.0278 0.1983 0.2256 0.071 Uiso 1 1 calc R . .
C5 C 0.1734(4) 0.2879(3) 0.1974(3) 0.0502(8) Uani 1 1 d . . .
H5 H 0.1963 0.2171 0.1437 0.060 Uiso 1 1 calc R . .
C6 C 0.2729(3) 0.4018(3) 0.2267(2) 0.0373(6) Uani 1 1 d . . .
C7 C 0.4151(3) 0.4071(3) 0.1703(2) 0.0360(6) Uani 1 1 d . . .
C8 C 0.6298(3) 0.5541(3) 0.1432(2) 0.0371(7) Uani 1 1 d . . .
C9 C 0.7485(4) 0.4954(3) 0.1445(3) 0.0445(7) Uani 1 1 d . . .
H9 H 0.7326 0.4266 0.1647 0.053 Uiso 1 1 calc R . .
C10 C 0.8896(4) 0.5370(3) 0.1164(3) 0.0497(8) Uani 1 1 d . . .
H10 H 0.9705 0.4967 0.1175 0.060 Uiso 1 1 calc R . .
C11 C 0.9136(4) 0.6370(3) 0.0867(3) 0.0471(8) Uani 1 1 d . . .
H11 H 1.0103 0.6648 0.0668 0.057 Uiso 1 1 calc R . .
C12 C 0.7968(3) 0.6961(3) 0.0861(2) 0.0419(7) Uani 1 1 d . . .
H12 H 0.8137 0.7652 0.0664 0.050 Uiso 1 1 calc R . .
C13 C 0.6548(3) 0.6555(3) 0.1140(2) 0.0351(6) Uani 1 1 d . . .
C14 C 0.4587(3) 0.7691(2) 0.1909(2) 0.0341(6) Uani 1 1 d . . .
C15 C 0.3516(3) 0.8409(3) 0.1682(2) 0.0347(6) Uani 1 1 d . . .
C16 C 0.2549(3) 0.8862(3) 0.2446(2) 0.0409(7) Uani 1 1 d . . .
H16 H 0.2578 0.8743 0.3121 0.049 Uiso 1 1 calc R . .
C17 C 0.1544(4) 0.9489(3) 0.2207(3) 0.0460(8) Uani 1 1 d . . .
H17 H 0.0848 0.9790 0.2706 0.055 Uiso 1 1 calc R . .
C18 C 0.1564(3) 0.9672(3) 0.1229(3) 0.0414(7) Uani 1 1 d . . .
H18 H 0.0885 1.0103 0.1044 0.050 Uiso 1 1 calc R . .
C19 C 0.2598(3) 0.9213(3) 0.0523(2) 0.0349(6) Uani 1 1 d . . .
C20 C 0.2661(3) 0.9450(3) -0.0528(2) 0.0371(6) Uani 1 1 d . . .
C21 C 0.3658(3) 0.8791(3) -0.2337(2) 0.0396(7) Uani 1 1 d . . .
C22 C 0.4446(5) 0.7974(4) -0.2979(3) 0.0695(12) Uani 1 1 d . . .
H22 H 0.4873 0.7476 -0.2688 0.083 Uiso 1 1 calc R . .
C23 C 0.4616(6) 0.7879(5) -0.4047(3) 0.0888(16) Uani 1 1 d . . .
H23 H 0.5148 0.7304 -0.4487 0.107 Uiso 1 1 calc R . .
C24 C 0.4029(5) 0.8601(4) -0.4483(3) 0.0662(10) Uani 1 1 d . . .
H24 H 0.4146 0.8527 -0.5220 0.079 Uiso 1 1 calc R . .
C25 C 0.3275(4) 0.9427(3) -0.3832(3) 0.0526(8) Uani 1 1 d . . .
H25 H 0.2881 0.9941 -0.4119 0.063 Uiso 1 1 calc R . .
C26 C 0.3072(4) 0.9533(3) -0.2765(3) 0.0431(7) Uani 1 1 d . . .
H26 H 0.2535 1.0108 -0.2329 0.052 Uiso 1 1 calc R . .
Cl1A Cl 0.7213(5) 0.5934(4) 0.4344(4) 0.0623(8) Uani 0.50 1 d P A 1
Cl2A Cl 0.9526(6) 0.8211(4) 0.4958(3) 0.1103(13) Uani 0.50 1 d P A 1
Cl1B Cl 0.7465(10) 0.6115(9) 0.4447(7) 0.176(4) Uani 0.50 1 d P A 2
Cl2B Cl 0.9465(8) 0.8374(12) 0.4537(8) 0.286(6) Uani 0.50 1 d P A 2
C100 C 0.7907(8) 0.7326(6) 0.4113(6) 0.133(3) Uani 1 1 d . . .
H10A H 0.8101 0.7101 0.3333 0.160 Uiso 1 1 calc R A 1
H10B H 0.7100 0.7799 0.4230 0.160 Uiso 1 1 calc R A 1


_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 C7 1.238(3) . ?
O2 C14 1.244(3) . ?
O3 C20 1.233(3) . ?
N1 C7 1.341(4) . ?
N1 C8 1.420(4) . ?
N1 H1N 0.89(4) . ?
N2 C14 1.336(4) . ?
N2 C13 1.431(4) . ?
N2 H2N 0.94(3) . ?
N3 C20 1.344(4) . ?
N3 C21 1.421(4) . ?
N3 H3N 0.85(4) . ?
N4 C19 1.338(4) . ?
N4 C15 1.347(3) . ?
C1 C6 1.389(4) . ?
C1 C2 1.389(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.506(4) . ?
C8 C9 1.391(4) . ?
C8 C13 1.398(4) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(4) . ?
C12 H12 0.9500 . ?
C14 C15 1.501(4) . ?
C15 C16 1.385(4) . ?
C16 C17 1.378(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.512(4) . ?
C21 C22 1.377(5) . ?
C21 C26 1.389(4) . ?
C22 C23 1.382(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.375(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.367(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
Cl1A C100 1.815(9) . ?
Cl2A C100 1.669(7) . ?
Cl1B C100 1.661(11) . ?
Cl2B C100 1.592(10) . ?
C100 H10A 0.9900 . ?
C100 H10B 0.9900 . ?

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
C7 N1 C8 127.7(3) . . ?
C7 N1 H1N 120(2) . . ?
C8 N1 H1N 112(2) . . ?
C14 N2 C13 125.9(2) . . ?
C14 N2 H2N 117(2) . . ?
C13 N2 H2N 116.5(19) . . ?
C20 N3 C21 127.4(3) . . ?
C20 N3 H3N 113(2) . . ?
C21 N3 H3N 119(2) . . ?
C19 N4 C15 116.9(2) . . ?
C6 C1 C2 120.1(3) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 117.3(3) . . ?
C1 C6 C7 123.2(3) . . ?
O1 C7 N1 123.8(3) . . ?
O1 C7 C6 120.9(3) . . ?
N1 C7 C6 115.3(2) . . ?
C9 C8 C13 119.4(3) . . ?
C9 C8 N1 122.0(3) . . ?
C13 C8 N1 118.4(2) . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 119.8(3) . . ?
C12 C13 N2 117.6(2) . . ?
C8 C13 N2 122.6(2) . . ?
O2 C14 N2 123.8(3) . . ?
O2 C14 C15 120.4(2) . . ?
N2 C14 C15 115.8(2) . . ?
N4 C15 C16 123.4(3) . . ?
N4 C15 C14 117.0(2) . . ?
C16 C15 C14 119.7(2) . . ?
C17 C16 C15 118.7(3) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 119.0(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C19 118.6(3) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
N4 C19 C18 123.4(3) . . ?
N4 C19 C20 117.9(2) . . ?
C18 C19 C20 118.7(3) . . ?
O3 C20 N3 125.1(3) . . ?
O3 C20 C19 119.4(2) . . ?
N3 C20 C19 115.6(2) . . ?
C22 C21 C26 119.3(3) . . ?
C22 C21 N3 117.0(3) . . ?
C26 C21 N3 123.7(3) . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 121.3(4) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C25 C24 C23 118.3(3) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C24 C25 C26 121.7(3) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C25 C26 C21 119.4(3) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?
Cl2B C100 Cl1B 126.6(6) . . ?
Cl1B C100 Cl2A 105.0(5) . . ?
Cl2B C100 Cl1A 133.7(5) . . ?
Cl2A C100 Cl1A 112.3(4) . . ?
Cl2B C100 H10A 91.0 . . ?
Cl1B C100 H10A 112.7 . . ?
Cl2A C100 H10A 109.2 . . ?
Cl1A C100 H10A 109.2 . . ?
Cl2B C100 H10B 103.0 . . ?
Cl1B C100 H10B 112.9 . . ?
Cl2A C100 H10B 109.2 . . ?
Cl1A C100 H10B 109.2 . . ?
H10A C100 H10B 107.9 . . ?

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
C6 C1 C2 C3 1.5(5) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C4 C5 C6 C7 -179.9(3) . . . . ?
C2 C1 C6 C5 -1.6(5) . . . . ?
C2 C1 C6 C7 179.2(3) . . . . ?
C8 N1 C7 O1 -8.9(5) . . . . ?
C8 N1 C7 C6 172.9(3) . . . . ?
C5 C6 C7 O1 -15.1(4) . . . . ?
C1 C6 C7 O1 164.2(3) . . . . ?
C5 C6 C7 N1 163.1(3) . . . . ?
C1 C6 C7 N1 -17.6(4) . . . . ?
C7 N1 C8 C9 -30.9(5) . . . . ?
C7 N1 C8 C13 153.3(3) . . . . ?
C13 C8 C9 C10 -0.3(5) . . . . ?
N1 C8 C9 C10 -176.2(3) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C11 C12 C13 C8 0.1(5) . . . . ?
C11 C12 C13 N2 -178.2(3) . . . . ?
C9 C8 C13 C12 0.3(4) . . . . ?
N1 C8 C13 C12 176.3(3) . . . . ?
C9 C8 C13 N2 178.6(3) . . . . ?
N1 C8 C13 N2 -5.4(4) . . . . ?
C14 N2 C13 C12 -125.5(3) . . . . ?
C14 N2 C13 C8 56.2(4) . . . . ?
C13 N2 C14 O2 -6.1(4) . . . . ?
C13 N2 C14 C15 174.4(2) . . . . ?
C19 N4 C15 C16 1.1(4) . . . . ?
C19 N4 C15 C14 -179.6(2) . . . . ?
O2 C14 C15 N4 174.9(2) . . . . ?
N2 C14 C15 N4 -5.5(4) . . . . ?
O2 C14 C15 C16 -5.7(4) . . . . ?
N2 C14 C15 C16 173.8(3) . . . . ?
N4 C15 C16 C17 1.2(5) . . . . ?
C14 C15 C16 C17 -178.2(3) . . . . ?
C15 C16 C17 C18 -1.7(5) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C15 N4 C19 C18 -2.8(4) . . . . ?
C15 N4 C19 C20 177.4(2) . . . . ?
C17 C18 C19 N4 2.3(5) . . . . ?
C17 C18 C19 C20 -177.9(3) . . . . ?
C21 N3 C20 O3 -5.1(5) . . . . ?
C21 N3 C20 C19 173.8(3) . . . . ?
N4 C19 C20 O3 -171.7(3) . . . . ?
C18 C19 C20 O3 8.5(4) . . . . ?
N4 C19 C20 N3 9.3(4) . . . . ?
C18 C19 C20 N3 -170.5(3) . . . . ?
C20 N3 C21 C22 -172.2(3) . . . . ?
C20 N3 C21 C26 8.6(5) . . . . ?
C26 C21 C22 C23 -1.5(6) . . . . ?
N3 C21 C22 C23 179.3(4) . . . . ?
C21 C22 C23 C24 0.9(8) . . . . ?
C22 C23 C24 C25 0.3(8) . . . . ?
C23 C24 C25 C26 -1.1(6) . . . . ?
C24 C25 C26 C21 0.6(5) . . . . ?
C22 C21 C26 C25 0.7(5) . . . . ?
N3 C21 C26 C25 179.9(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
N1 H1N O2 0.89(4) 1.91(4) 2.730(3) 151(3) .
N2 H2N O1 0.94(3) 2.02(3) 2.869(3) 150(3) 2_665
N3 H3N N4 0.85(4) 2.28(3) 2.725(3) 113(3) .
N2 H2N N4 0.94(3) 2.26(3) 2.695(3) 107(2) .
N3 H3N O1 0.85(4) 2.41(4) 3.200(3) 155(3) 2_665

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        66.68
_diffrn_measured_fraction_theta_full 0.951
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.059
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2-DCM-2-S1
_database_code_depnum_ccdc_archive 'CCDC 1436664'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 N4 O3, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C26.50 H21 Cl N4 O3'
_chemical_formula_weight         478.92

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'
Cl Cl 0.3639 0.7018 '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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.01330(10)
_cell_length_b                   11.96530(10)
_cell_length_c                   12.00000(10)
_cell_angle_alpha                83.1420(10)
_cell_angle_beta                 81.2330(10)
_cell_angle_gamma                69.2130(10)
_cell_volume                     1192.793(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             498
_exptl_absorpt_coefficient_mu    1.717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6834
_exptl_absorpt_correction_T_max  0.7252
_exptl_absorpt_process_details   
;
Denzo (otwinowski, Borek, Majewski & Minor, 2003) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KappaCCD, Cu, APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5922
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.74
_diffrn_reflns_theta_max         66.98
_reflns_number_total             4093
_reflns_number_gt                3456
_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)+(0.0848P)²+0.4460P] 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         4093
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38501(17) 0.61254(13) 0.73148(12) 0.0428(4) Uani 1 1 d . . .
O2 O 0.2634(2) 0.81120(13) 0.35446(13) 0.0499(4) Uani 1 1 d . . .
O3 O 0.23920(19) 0.43522(15) -0.04243(13) 0.0524(4) Uani 1 1 d . . .
N1 N 0.3648(2) 0.70063(17) 0.55291(15) 0.0407(4) Uani 1 1 d . . .
H1N H 0.298(3) 0.743(3) 0.508(2) 0.061 Uiso 1 1 d . . .
N2 N 0.4576(2) 0.62964(16) 0.32691(15) 0.0390(4) Uani 1 1 d . . .
H2N H 0.487(3) 0.569(3) 0.292(2) 0.058 Uiso 1 1 d . . .
N3 N 0.4398(2) 0.37670(16) 0.07073(15) 0.0402(4) Uani 1 1 d . . .
H3N H 0.474(3) 0.402(3) 0.122(2) 0.060 Uiso 1 1 d . . .
N4 N 0.30098(19) 0.58713(15) 0.17264(14) 0.0369(4) Uani 1 1 d . . .
C1 C 0.0379(3) 0.8393(2) 0.6242(2) 0.0517(6) Uani 1 1 d . . .
H1 H 0.0897 0.8751 0.5630 0.062 Uiso 1 1 calc R . .
C2 C -0.1259(3) 0.8887(2) 0.6527(2) 0.0573(6) Uani 1 1 d . . .
H2 H -0.1860 0.9584 0.6109 0.069 Uiso 1 1 calc R . .
C3 C -0.2019(3) 0.8374(2) 0.7410(2) 0.0522(6) Uani 1 1 d . . .
H3 H -0.3145 0.8707 0.7592 0.063 Uiso 1 1 calc R . .
C4 C -0.1149(3) 0.7379(2) 0.8031(2) 0.0515(6) Uani 1 1 d . . .
H4 H -0.1676 0.7038 0.8651 0.062 Uiso 1 1 calc R . .
C5 C 0.0494(3) 0.6870(2) 0.77617(18) 0.0445(5) Uani 1 1 d . . .
H5 H 0.1087 0.6183 0.8195 0.053 Uiso 1 1 calc R . .
C6 C 0.1268(2) 0.73686(18) 0.68553(17) 0.0388(5) Uani 1 1 d . . .
C7 C 0.3033(2) 0.67833(18) 0.65933(17) 0.0383(5) Uani 1 1 d . . .
C8 C 0.5276(2) 0.66509(18) 0.50796(17) 0.0386(5) Uani 1 1 d . . .
C9 C 0.6457(3) 0.6644(2) 0.57135(19) 0.0459(5) Uani 1 1 d . . .
H9 H 0.6177 0.6851 0.6476 0.055 Uiso 1 1 calc R . .
C10 C 0.8030(3) 0.6338(2) 0.5235(2) 0.0505(6) Uani 1 1 d . . .
H10 H 0.8830 0.6326 0.5673 0.061 Uiso 1 1 calc R . .
C11 C 0.8447(3) 0.6047(2) 0.4118(2) 0.0493(6) Uani 1 1 d . . .
H11 H 0.9530 0.5840 0.3791 0.059 Uiso 1 1 calc R . .
C12 C 0.7287(3) 0.6059(2) 0.34806(19) 0.0445(5) Uani 1 1 d . . .
H12 H 0.7574 0.5863 0.2715 0.053 Uiso 1 1 calc R . .
C13 C 0.5702(2) 0.63555(18) 0.39545(17) 0.0379(5) Uani 1 1 d . . .
C14 C 0.3186(2) 0.71599(18) 0.30798(17) 0.0393(5) Uani 1 1 d . . .
C15 C 0.2287(2) 0.68765(19) 0.22691(17) 0.0391(5) Uani 1 1 d . . .
C16 C 0.0750(3) 0.7653(2) 0.21188(19) 0.0483(5) Uani 1 1 d . . .
H16 H 0.0284 0.8365 0.2509 0.058 Uiso 1 1 calc R . .
C17 C -0.0078(3) 0.7363(2) 0.1389(2) 0.0528(6) Uani 1 1 d . . .
H17 H -0.1137 0.7865 0.1279 0.063 Uiso 1 1 calc R . .
C18 C 0.0651(3) 0.6334(2) 0.08196(19) 0.0485(6) Uani 1 1 d . . .
H18 H 0.0101 0.6115 0.0315 0.058 Uiso 1 1 calc R . .
C19 C 0.2200(2) 0.56268(19) 0.09964(17) 0.0395(5) Uani 1 1 d . . .
C20 C 0.3016(3) 0.45232(19) 0.03503(17) 0.0405(5) Uani 1 1 d . . .
C21 C 0.5350(3) 0.26321(19) 0.03102(17) 0.0410(5) Uani 1 1 d . . .
C22 C 0.4909(3) 0.2080(2) -0.0475(2) 0.0510(6) Uani 1 1 d . . .
H22 H 0.3931 0.2468 -0.0788 0.061 Uiso 1 1 calc R . .
C23 C 0.5908(3) 0.0958(2) -0.0799(2) 0.0600(7) Uani 1 1 d . . .
H23 H 0.5603 0.0582 -0.1335 0.072 Uiso 1 1 calc R . .
C24 C 0.7331(3) 0.0378(2) -0.0361(2) 0.0626(7) Uani 1 1 d . . .
H24 H 0.8000 -0.0393 -0.0585 0.075 Uiso 1 1 calc R . .
C25 C 0.7769(3) 0.0937(3) 0.0411(2) 0.0642(7) Uani 1 1 d . . .
H25 H 0.8753 0.0548 0.0716 0.077 Uiso 1 1 calc R . .
C26 C 0.6792(3) 0.2054(2) 0.0742(2) 0.0518(6) Uani 1 1 d . . .
H26 H 0.7111 0.2429 0.1271 0.062 Uiso 1 1 calc R . .
C100 C 0.5789(11) 0.9243(6) 0.4095(7) 0.097(3) Uani 0.50 1 d P A -1
H10A H 0.6711 0.8558 0.4337 0.117 Uiso 0.50 1 calc PR A -1
H10B H 0.5096 0.8922 0.3762 0.117 Uiso 0.50 1 calc PR A -1
Cl1 Cl 0.6463(2) 1.01600(16) 0.3095(2) 0.1014(6) Uani 0.50 1 d P A -1
Cl2 Cl 0.4652(3) 1.0072(3) 0.5335(2) 0.1070(8) Uani 0.50 1 d P A -1


_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 C7 1.237(2) . ?
O2 C14 1.233(2) . ?
O3 C20 1.228(2) . ?
N1 C7 1.348(3) . ?
N1 C8 1.413(3) . ?
N1 H1N 0.86(3) . ?
N2 C14 1.342(3) . ?
N2 C13 1.425(3) . ?
N2 H2N 0.82(3) . ?
N3 C20 1.350(3) . ?
N3 C21 1.418(3) . ?
N3 H3N 0.85(3) . ?
N4 C19 1.339(3) . ?
N4 C15 1.340(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.397(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.376(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.494(3) . ?
C8 C9 1.396(3) . ?
C8 C13 1.398(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.494(3) . ?
C15 C16 1.392(3) . ?
C16 C17 1.379(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.506(3) . ?
C21 C26 1.385(3) . ?
C21 C22 1.390(3) . ?
C22 C23 1.387(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C100 Cl1 1.717(8) . ?
C100 Cl2 1.848(9) . ?
C100 H10A 0.9900 . ?
C100 H10B 0.9900 . ?

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
C7 N1 C8 127.53(18) . . ?
C7 N1 H1N 116.5(18) . . ?
C8 N1 H1N 115.9(18) . . ?
C14 N2 C13 126.50(18) . . ?
C14 N2 H2N 118.6(19) . . ?
C13 N2 H2N 114.6(19) . . ?
C20 N3 C21 127.49(18) . . ?
C20 N3 H3N 115.7(19) . . ?
C21 N3 H3N 116.8(19) . . ?
C19 N4 C15 117.34(17) . . ?
C2 C1 C6 120.0(2) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 C7 117.80(19) . . ?
C1 C6 C7 122.9(2) . . ?
O1 C7 N1 123.29(19) . . ?
O1 C7 C6 121.11(19) . . ?
N1 C7 C6 115.59(18) . . ?
C9 C8 C13 119.29(19) . . ?
C9 C8 N1 121.62(19) . . ?
C13 C8 N1 119.01(17) . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 119.91(18) . . ?
C12 C13 N2 117.57(18) . . ?
C8 C13 N2 122.47(18) . . ?
O2 C14 N2 124.32(19) . . ?
O2 C14 C15 120.80(18) . . ?
N2 C14 C15 114.85(17) . . ?
N4 C15 C16 123.28(19) . . ?
N4 C15 C14 117.69(17) . . ?
C16 C15 C14 119.03(19) . . ?
C17 C16 C15 118.3(2) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C16 C17 C18 119.2(2) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C19 118.8(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
N4 C19 C18 123.0(2) . . ?
N4 C19 C20 118.03(18) . . ?
C18 C19 C20 118.92(19) . . ?
O3 C20 N3 124.8(2) . . ?
O3 C20 C19 119.65(19) . . ?
N3 C20 C19 115.53(18) . . ?
C26 C21 C22 119.1(2) . . ?
C26 C21 N3 117.26(19) . . ?
C22 C21 N3 123.6(2) . . ?
C23 C22 C21 119.5(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C24 C23 C22 121.4(2) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C25 118.8(3) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C21 120.5(2) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
Cl1 C100 Cl2 110.8(4) . . ?
Cl1 C100 H10A 109.5 . . ?
Cl2 C100 H10A 109.5 . . ?
Cl1 C100 H10B 109.5 . . ?
Cl2 C100 H10B 109.5 . . ?
H10A C100 H10B 108.1 . . ?

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
C6 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C4 C5 C6 C7 -179.56(19) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
C2 C1 C6 C7 179.7(2) . . . . ?
C8 N1 C7 O1 -6.5(3) . . . . ?
C8 N1 C7 C6 174.62(18) . . . . ?
C5 C6 C7 O1 -20.9(3) . . . . ?
C1 C6 C7 O1 158.3(2) . . . . ?
C5 C6 C7 N1 158.03(19) . . . . ?
C1 C6 C7 N1 -22.8(3) . . . . ?
C7 N1 C8 C9 -37.8(3) . . . . ?
C7 N1 C8 C13 145.3(2) . . . . ?
C13 C8 C9 C10 -0.6(3) . . . . ?
N1 C8 C9 C10 -177.4(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C8 0.4(3) . . . . ?
C11 C12 C13 N2 -177.1(2) . . . . ?
C9 C8 C13 C12 0.1(3) . . . . ?
N1 C8 C13 C12 176.97(19) . . . . ?
C9 C8 C13 N2 177.42(19) . . . . ?
N1 C8 C13 N2 -5.7(3) . . . . ?
C14 N2 C13 C12 -128.9(2) . . . . ?
C14 N2 C13 C8 53.7(3) . . . . ?
C13 N2 C14 O2 -5.2(3) . . . . ?
C13 N2 C14 C15 176.61(18) . . . . ?
C19 N4 C15 C16 0.9(3) . . . . ?
C19 N4 C15 C14 -179.63(17) . . . . ?
O2 C14 C15 N4 174.81(19) . . . . ?
N2 C14 C15 N4 -6.9(3) . . . . ?
O2 C14 C15 C16 -5.7(3) . . . . ?
N2 C14 C15 C16 172.6(2) . . . . ?
N4 C15 C16 C17 1.1(3) . . . . ?
C14 C15 C16 C17 -178.4(2) . . . . ?
C15 C16 C17 C18 -1.3(4) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C15 N4 C19 C18 -2.6(3) . . . . ?
C15 N4 C19 C20 177.96(18) . . . . ?
C17 C18 C19 N4 2.4(3) . . . . ?
C17 C18 C19 C20 -178.2(2) . . . . ?
C21 N3 C20 O3 -2.9(3) . . . . ?
C21 N3 C20 C19 175.25(18) . . . . ?
N4 C19 C20 O3 -170.94(19) . . . . ?
C18 C19 C20 O3 9.6(3) . . . . ?
N4 C19 C20 N3 10.8(3) . . . . ?
C18 C19 C20 N3 -168.59(19) . . . . ?
C20 N3 C21 C26 175.0(2) . . . . ?
C20 N3 C21 C22 -5.3(3) . . . . ?
C26 C21 C22 C23 0.8(3) . . . . ?
N3 C21 C22 C23 -178.9(2) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C25 -0.5(4) . . . . ?
C23 C24 C25 C26 0.4(4) . . . . ?
C24 C25 C26 C21 0.3(4) . . . . ?
C22 C21 C26 C25 -0.9(4) . . . . ?
N3 C21 C26 C25 178.8(2) . . . . ?

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 O2 0.86(3) 1.94(3) 2.704(2) 147(3) .
N2 H2N O1 0.82(3) 2.10(3) 2.857(2) 154(3) 2_666
N2 H2N N4 0.82(3) 2.30(3) 2.685(2) 109(2) .
N3 H3N O1 0.85(3) 2.28(3) 3.083(2) 157(3) 2_666
N3 H3N N4 0.85(3) 2.31(3) 2.726(3) 111(2) .

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        66.98
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.064
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2-DMA-at
_database_code_depnum_ccdc_archive 'CCDC 1436665'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 N4 O3, C4 H9 N O'
_chemical_formula_sum            'C30 H29 N5 O4'
_chemical_formula_weight         523.58

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1890(2)
_cell_length_b                   12.1939(3)
_cell_length_c                   14.5599(3)
_cell_angle_alpha                68.849(2)
_cell_angle_beta                 80.180(3)
_cell_angle_gamma                86.555(3)
_cell_volume                     1336.08(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8697
_exptl_absorpt_correction_T_max  0.9317
_exptl_absorpt_process_details   
;
Denzo (otwinowski, Borek, Majewski & Minor, 2003) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KappaCCD, Cu, APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6464
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         66.52
_reflns_number_total             4349
_reflns_number_gt                2990
_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)+(0.0601P)²+0.3024P] 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         4349
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1369
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1702(2) 0.70331(14) 0.75552(12) 0.0458(4) Uani 1 1 d . . .
O2 O 0.2627(2) 1.01715(15) 0.88597(13) 0.0568(5) Uani 1 1 d . . .
O3 O 0.2842(3) 1.04681(16) 0.39353(13) 0.0642(6) Uani 1 1 d . . .
N1 N 0.2730(2) 0.61135(18) 0.89990(14) 0.0385(5) Uani 1 1 d . . .
H1N H 0.330(3) 0.548(2) 0.9298(18) 0.046 Uiso 1 1 d . . .
N2 N 0.2018(3) 0.86042(18) 0.84593(15) 0.0454(5) Uani 1 1 d . . .
H2N H 0.195(3) 0.838(2) 0.7967(19) 0.055 Uiso 1 1 d . . .
N3 N 0.1693(3) 0.89191(19) 0.52969(16) 0.0477(5) Uani 1 1 d . . .
H3N H 0.157(3) 0.865(2) 0.598(2) 0.057 Uiso 1 1 d . . .
N4 N 0.2647(2) 0.98862(17) 0.65178(14) 0.0423(5) Uani 1 1 d . . .
C1 C 0.5337(3) 0.5191(2) 0.78430(19) 0.0492(6) Uani 1 1 d . . .
H1 H 0.5669 0.5325 0.8388 0.059 Uiso 1 1 calc R . .
C2 C 0.6350(3) 0.4555(3) 0.7351(2) 0.0568(7) Uani 1 1 d . . .
H2 H 0.7388 0.4273 0.7551 0.068 Uiso 1 1 calc R . .
C3 C 0.5867(3) 0.4328(2) 0.65735(19) 0.0527(7) Uani 1 1 d . . .
H3 H 0.6560 0.3883 0.6246 0.063 Uiso 1 1 calc R . .
C4 C 0.4361(3) 0.4756(2) 0.62752(18) 0.0470(6) Uani 1 1 d . . .
H4 H 0.4007 0.4587 0.5752 0.056 Uiso 1 1 calc R . .
C5 C 0.3376(3) 0.5426(2) 0.67370(17) 0.0403(6) Uani 1 1 d . . .
H5 H 0.2373 0.5751 0.6507 0.048 Uiso 1 1 calc R . .
C6 C 0.3841(3) 0.56307(19) 0.75401(16) 0.0364(5) Uani 1 1 d . . .
C7 C 0.2674(3) 0.6322(2) 0.80288(17) 0.0373(5) Uani 1 1 d . . .
C8 C 0.1657(3) 0.6593(2) 0.96424(16) 0.0381(5) Uani 1 1 d . . .
C9 C 0.0975(3) 0.5805(2) 1.05743(17) 0.0467(6) Uani 1 1 d . . .
H9 H 0.1185 0.4987 1.0740 0.056 Uiso 1 1 calc R . .
C10 C -0.0013(3) 0.6209(3) 1.12650(19) 0.0534(7) Uani 1 1 d . . .
H10 H -0.0459 0.5669 1.1903 0.064 Uiso 1 1 calc R . .
C11 C -0.0342(3) 0.7390(3) 1.10222(19) 0.0522(7) Uani 1 1 d . . .
H11 H -0.1030 0.7661 1.1492 0.063 Uiso 1 1 calc R . .
C12 C 0.0314(3) 0.8181(2) 1.01070(19) 0.0485(6) Uani 1 1 d . . .
H12 H 0.0070 0.8995 0.9946 0.058 Uiso 1 1 calc R . .
C13 C 0.1345(3) 0.7795(2) 0.94062(17) 0.0405(6) Uani 1 1 d . . .
C14 C 0.2549(3) 0.9712(2) 0.82409(18) 0.0447(6) Uani 1 1 d . . .
C15 C 0.3087(3) 1.0359(2) 0.71439(18) 0.0439(6) Uani 1 1 d . . .
C16 C 0.3989(3) 1.1398(2) 0.6811(2) 0.0496(7) Uani 1 1 d . . .
H16 H 0.4281 1.1707 0.7274 0.060 Uiso 1 1 calc R . .
C17 C 0.4451(4) 1.1973(2) 0.5801(2) 0.0550(7) Uani 1 1 d . . .
H17 H 0.5091 1.2673 0.5556 0.066 Uiso 1 1 calc R . .
C18 C 0.3966(3) 1.1512(2) 0.5147(2) 0.0524(7) Uani 1 1 d . . .
H18 H 0.4242 1.1901 0.4446 0.063 Uiso 1 1 calc R . .
C19 C 0.3067(3) 1.0469(2) 0.55392(18) 0.0433(6) Uani 1 1 d . . .
C20 C 0.2521(3) 0.9951(2) 0.48408(19) 0.0476(6) Uani 1 1 d . . .
C21 C 0.1034(3) 0.8234(2) 0.48408(18) 0.0457(6) Uani 1 1 d . . .
C22 C 0.0081(3) 0.7256(2) 0.5461(2) 0.0518(7) Uani 1 1 d . . .
H22 H -0.0126 0.7079 0.6161 0.062 Uiso 1 1 calc R . .
C23 C -0.0565(4) 0.6542(3) 0.5057(2) 0.0640(8) Uani 1 1 d . . .
H23 H -0.1198 0.5869 0.5485 0.077 Uiso 1 1 calc R . .
C24 C -0.0302(4) 0.6795(3) 0.4040(2) 0.0657(8) Uani 1 1 d . . .
H24 H -0.0753 0.6304 0.3765 0.079 Uiso 1 1 calc R . .
C25 C 0.0616(4) 0.7761(3) 0.3434(2) 0.0648(8) Uani 1 1 d . . .
H25 H 0.0796 0.7940 0.2733 0.078 Uiso 1 1 calc R . .
C26 C 0.1293(4) 0.8488(3) 0.3818(2) 0.0581(7) Uani 1 1 d . . .
H26 H 0.1930 0.9155 0.3383 0.070 Uiso 1 1 calc R . .
O100 O 0.3817(2) 0.37932(15) 0.02461(14) 0.0546(5) Uani 1 1 d . . .
N30A N 0.3774(8) 0.1871(5) 0.0532(6) 0.0518(16) Uani 0.670(16) 1 d P A 1
C30A C 0.3342(7) 0.2795(5) 0.0832(5) 0.042(2) Uani 0.670(16) 1 d P A 1
C31A C 0.4785(4) 0.2133(3) -0.0472(2) 0.0704(9) Uani 0.670(16) 1 d P A 1
H31A H 0.5075 0.2970 -0.0760 0.106 Uiso 0.670(16) 1 calc PR A 1
H31B H 0.4146 0.1940 -0.0905 0.106 Uiso 0.670(16) 1 calc PR A 1
H31C H 0.5800 0.1661 -0.0414 0.106 Uiso 0.670(16) 1 calc PR A 1
C32A C 0.3179(4) 0.0656(2) 0.1160(3) 0.0740(9) Uani 0.670(16) 1 d P A 1
H32A H 0.3579 0.0414 0.1802 0.111 Uiso 0.670(16) 1 calc PR A 1
H32B H 0.3604 0.0113 0.0817 0.111 Uiso 0.670(16) 1 calc PR A 1
H32C H 0.1965 0.0642 0.1275 0.111 Uiso 0.670(16) 1 calc PR A 1
C33A C 0.2311(4) 0.2466(3) 0.1855(2) 0.0716(9) Uani 0.670(16) 1 d P A 1
H33A H 0.3006 0.2056 0.2362 0.107 Uiso 0.670(16) 1 calc PR A 1
H33B H 0.1402 0.1949 0.1907 0.107 Uiso 0.670(16) 1 calc PR A 1
H33C H 0.1855 0.3179 0.1963 0.107 Uiso 0.670(16) 1 calc PR A 1
N30B N 0.3129(16) 0.1882(10) 0.1057(12) 0.054(4) Uani 0.330(16) 1 d P A 2
C30B C 0.3908(14) 0.2682(12) 0.0261(12) 0.047(4) Uani 0.330(16) 1 d P A 2
C31B C 0.4785(4) 0.2133(3) -0.0472(2) 0.0704(9) Uani 0.330(16) 1 d P A 2
H31D H 0.5237 0.2755 -0.1097 0.106 Uiso 0.330(16) 1 calc PR A 2
H31E H 0.3995 0.1657 -0.0605 0.106 Uiso 0.330(16) 1 calc PR A 2
H31F H 0.5689 0.1631 -0.0189 0.106 Uiso 0.330(16) 1 calc PR A 2
C32B C 0.3179(4) 0.0656(2) 0.1160(3) 0.0740(9) Uani 0.330(16) 1 d P A 2
H32D H 0.2971 0.0584 0.0541 0.111 Uiso 0.330(16) 1 calc PR A 2
H32E H 0.2327 0.0221 0.1713 0.111 Uiso 0.330(16) 1 calc PR A 2
H32F H 0.4273 0.0331 0.1298 0.111 Uiso 0.330(16) 1 calc PR A 2
C33B C 0.2311(4) 0.2466(3) 0.1855(2) 0.0716(9) Uani 0.330(16) 1 d P A 2
H33D H 0.2836 0.2144 0.2454 0.107 Uiso 0.330(16) 1 calc PR A 2
H33E H 0.1122 0.2291 0.2035 0.107 Uiso 0.330(16) 1 calc PR A 2
H33F H 0.2476 0.3320 0.1564 0.107 Uiso 0.330(16) 1 calc PR A 2


_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 C7 1.238(3) . ?
O2 C14 1.232(3) . ?
O3 C20 1.228(3) . ?
N1 C7 1.351(3) . ?
N1 C8 1.430(3) . ?
N1 H1N 0.88(2) . ?
N2 C14 1.352(3) . ?
N2 C13 1.415(3) . ?
N2 H2N 0.86(3) . ?
N3 C20 1.353(3) . ?
N3 C21 1.416(3) . ?
N3 H3N 0.91(3) . ?
N4 C19 1.336(3) . ?
N4 C15 1.345(3) . ?
C1 C6 1.384(3) . ?
C1 C2 1.387(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.495(3) . ?
C8 C9 1.394(3) . ?
C8 C13 1.397(3) . ?
C9 C10 1.394(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.408(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.503(3) . ?
C15 C16 1.390(4) . ?
C16 C17 1.377(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.512(4) . ?
C21 C26 1.387(3) . ?
C21 C22 1.393(4) . ?
C22 C23 1.384(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.364(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
O100 C30A 1.247(6) . ?
O100 C30B 1.345(15) . ?
N30A C30A 1.356(13) . ?
N30A C31A 1.486(9) . ?
N30A C32A 1.492(7) . ?
C30A C33A 1.508(8) . ?
C31A H31A 0.9800 . ?
C31A H31B 0.9800 . ?
C31A H31C 0.9800 . ?
C32A H32A 0.9800 . ?
C32A H32B 0.9800 . ?
C32A H32C 0.9800 . ?
C33A H33A 0.9800 . ?
C33A H33B 0.9800 . ?
C33A H33C 0.9800 . ?
N30B C30B 1.31(3) . ?

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
C7 N1 C8 126.8(2) . . ?
C7 N1 H1N 115.1(16) . . ?
C8 N1 H1N 115.9(16) . . ?
C14 N2 C13 127.5(2) . . ?
C14 N2 H2N 117.6(18) . . ?
C13 N2 H2N 114.4(18) . . ?
C20 N3 C21 127.5(2) . . ?
C20 N3 H3N 114.0(17) . . ?
C21 N3 H3N 118.4(17) . . ?
C19 N4 C15 117.7(2) . . ?
C6 C1 C2 120.0(2) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 C7 123.5(2) . . ?
C5 C6 C7 117.3(2) . . ?
O1 C7 N1 122.9(2) . . ?
O1 C7 C6 120.5(2) . . ?
N1 C7 C6 116.6(2) . . ?
C9 C8 C13 119.5(2) . . ?
C9 C8 N1 116.8(2) . . ?
C13 C8 N1 123.6(2) . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 119.2(2) . . ?
C8 C13 N2 120.0(2) . . ?
C12 C13 N2 120.7(2) . . ?
O2 C14 N2 125.0(2) . . ?
O2 C14 C15 121.5(2) . . ?
N2 C14 C15 113.5(2) . . ?
N4 C15 C16 122.6(2) . . ?
N4 C15 C14 116.8(2) . . ?
C16 C15 C14 120.5(2) . . ?
C17 C16 C15 119.0(2) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 118.9(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C17 C18 C19 118.5(2) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
N4 C19 C18 123.2(2) . . ?
N4 C19 C20 117.3(2) . . ?
C18 C19 C20 119.5(2) . . ?
O3 C20 N3 125.4(2) . . ?
O3 C20 C19 119.8(2) . . ?
N3 C20 C19 114.9(2) . . ?
C26 C21 C22 118.9(3) . . ?
C26 C21 N3 123.5(3) . . ?
C22 C21 N3 117.6(2) . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 118.9(3) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C24 C25 C26 121.6(3) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C21 C26 C25 119.7(3) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C30A O100 C30B 41.9(5) . . ?
C30A N30A C31A 117.1(7) . . ?
C30A N30A C32A 121.3(8) . . ?
C31A N30A C32A 121.5(5) . . ?
O100 C30A N30A 117.7(9) . . ?
O100 C30A C33A 128.1(6) . . ?
N30A C30A C33A 114.2(6) . . ?
N30A C31A H31A 109.5 . . ?
N30A C31A H31B 109.5 . . ?
H31A C31A H31B 109.5 . . ?
N30A C31A H31C 109.5 . . ?
H31A C31A H31C 109.5 . . ?
H31B C31A H31C 109.5 . . ?
N30A C32A H32A 109.5 . . ?
N30A C32A H32B 109.5 . . ?
H32A C32A H32B 109.5 . . ?
N30A C32A H32C 109.5 . . ?
H32A C32A H32C 109.5 . . ?
H32B C32A H32C 109.5 . . ?
C30A C33A H33A 109.5 . . ?
C30A C33A H33B 109.5 . . ?
H33A C33A H33B 109.5 . . ?
C30A C33A H33C 109.5 . . ?
H33A C33A H33C 109.5 . . ?
H33B C33A H33C 109.5 . . ?
N30B C30B O100 116.6(19) . . ?

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
C6 C1 C2 C3 -1.6(4) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C3 C4 C5 C6 -3.3(4) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C1 C6 C7 179.9(2) . . . . ?
C4 C5 C6 C1 2.5(4) . . . . ?
C4 C5 C6 C7 -177.4(2) . . . . ?
C8 N1 C7 O1 4.3(4) . . . . ?
C8 N1 C7 C6 -174.8(2) . . . . ?
C1 C6 C7 O1 153.9(2) . . . . ?
C5 C6 C7 O1 -26.1(3) . . . . ?
C1 C6 C7 N1 -27.0(3) . . . . ?
C5 C6 C7 N1 153.0(2) . . . . ?
C7 N1 C8 C9 131.7(2) . . . . ?
C7 N1 C8 C13 -52.0(3) . . . . ?
C13 C8 C9 C10 0.1(3) . . . . ?
N1 C8 C9 C10 176.6(2) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C9 C8 C13 C12 -1.5(3) . . . . ?
N1 C8 C13 C12 -177.8(2) . . . . ?
C9 C8 C13 N2 -179.4(2) . . . . ?
N1 C8 C13 N2 4.3(3) . . . . ?
C11 C12 C13 C8 1.7(4) . . . . ?
C11 C12 C13 N2 179.6(2) . . . . ?
C14 N2 C13 C8 -145.7(2) . . . . ?
C14 N2 C13 C12 36.4(4) . . . . ?
C13 N2 C14 O2 5.0(4) . . . . ?
C13 N2 C14 C15 -176.1(2) . . . . ?
C19 N4 C15 C16 -1.8(3) . . . . ?
C19 N4 C15 C14 177.9(2) . . . . ?
O2 C14 C15 N4 -166.8(2) . . . . ?
N2 C14 C15 N4 14.2(3) . . . . ?
O2 C14 C15 C16 12.9(4) . . . . ?
N2 C14 C15 C16 -166.1(2) . . . . ?
N4 C15 C16 C17 0.1(4) . . . . ?
C14 C15 C16 C17 -179.5(2) . . . . ?
C15 C16 C17 C18 1.6(4) . . . . ?
C16 C17 C18 C19 -1.7(4) . . . . ?
C15 N4 C19 C18 1.8(3) . . . . ?
C15 N4 C19 C20 -178.2(2) . . . . ?
C17 C18 C19 N4 0.0(4) . . . . ?
C17 C18 C19 C20 179.9(2) . . . . ?
C21 N3 C20 O3 -0.1(4) . . . . ?
C21 N3 C20 C19 179.9(2) . . . . ?
N4 C19 C20 O3 178.3(2) . . . . ?
C18 C19 C20 O3 -1.7(4) . . . . ?
N4 C19 C20 N3 -1.8(3) . . . . ?
C18 C19 C20 N3 178.3(2) . . . . ?
C20 N3 C21 C26 6.4(4) . . . . ?
C20 N3 C21 C22 -173.8(2) . . . . ?
C26 C21 C22 C23 1.2(4) . . . . ?
N3 C21 C22 C23 -178.7(2) . . . . ?
C21 C22 C23 C24 -1.1(4) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C23 C24 C25 C26 0.3(5) . . . . ?
C22 C21 C26 C25 -0.6(4) . . . . ?
N3 C21 C26 C25 179.3(2) . . . . ?
C24 C25 C26 C21 -0.1(4) . . . . ?
C30B O100 C30A N30A 1.9(6) . . . . ?
C30B O100 C30A C33A -177.5(8) . . . . ?
C31A N30A C30A O100 0.2(5) . . . . ?
C32A N30A C30A O100 -176.5(3) . . . . ?
C31A N30A C30A C33A 179.7(3) . . . . ?
C32A N30A C30A C33A 3.1(5) . . . . ?
C30A O100 C30B N30B 3.0(5) . . . . ?

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 O100 0.88(2) 2.09(3) 2.939(3) 160(2) 1_556
N2 H2N N4 0.86(3) 2.25(3) 2.667(3) 110(2) .
N2 H2N O1 0.86(3) 1.98(3) 2.732(3) 146(2) .
N3 H3N N4 0.91(3) 2.22(3) 2.694(3) 112(2) .
N3 H3N O1 0.91(3) 2.45(3) 3.263(3) 149(2) .

_diffrn_measured_fraction_theta_max 0.923
_diffrn_reflns_theta_full        66.52
_diffrn_measured_fraction_theta_full 0.923
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.046
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2-Form-II-at
_database_code_depnum_ccdc_archive 'CCDC 1436666'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 N4 O3'
_chemical_formula_sum            'C26 H20 N4 O3'
_chemical_formula_weight         436.46

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   10.9333(6)
_cell_length_b                   18.0540(11)
_cell_length_c                   21.5317(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4250.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8187
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_process_details   
;
Denzo (otwinowski, Borek, Majewski & Minor, 2003) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KappaCCD, Cu, APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6664
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.11
_diffrn_reflns_theta_max         66.77
_reflns_number_total             3634
_reflns_number_gt                2276
_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)+(0.0573P)²+0.9474P] 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         3634
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1350
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.18120(17) 0.15574(11) 0.63675(8) 0.0443(5) Uani 1 1 d . . .
O2 O -0.26633(17) 0.13015(11) 0.63517(8) 0.0448(5) Uani 1 1 d . . .
O3 O 0.1565(2) 0.09439(14) 0.39280(9) 0.0685(7) Uani 1 1 d . . .
N1 N 0.1243(2) 0.14186(13) 0.73798(10) 0.0392(6) Uani 1 1 d . . .
H1N H 0.153(3) 0.1280(15) 0.7752(13) 0.047 Uiso 1 1 d . . .
N2 N -0.0636(2) 0.16244(13) 0.64256(10) 0.0401(6) Uani 1 1 d . . .
H2N H 0.011(3) 0.1584(15) 0.6236(12) 0.048 Uiso 1 1 d . . .
N3 N 0.2105(2) 0.13348(13) 0.48972(11) 0.0406(6) Uani 1 1 d . . .
H3N H 0.175(3) 0.1386(15) 0.5279(13) 0.049 Uiso 1 1 d . . .
N4 N -0.0198(2) 0.11272(12) 0.52928(9) 0.0376(6) Uani 1 1 d . . .
C1 C 0.2923(3) 0.01926(16) 0.74704(13) 0.0432(7) Uani 1 1 d . . .
H1 H 0.2279 0.0206 0.7767 0.052 Uiso 1 1 calc R . .
C2 C 0.3845(3) -0.03261(16) 0.75309(13) 0.0462(8) Uani 1 1 d . . .
H2 H 0.3836 -0.0663 0.7870 0.055 Uiso 1 1 calc R . .
C3 C 0.4776(3) -0.03559(16) 0.71018(13) 0.0462(7) Uani 1 1 d . . .
H3 H 0.5398 -0.0721 0.7137 0.055 Uiso 1 1 calc R . .
C4 C 0.4802(3) 0.01537(17) 0.66156(13) 0.0471(8) Uani 1 1 d . . .
H4 H 0.5456 0.0146 0.6325 0.056 Uiso 1 1 calc R . .
C5 C 0.3883(3) 0.06661(16) 0.65568(12) 0.0407(7) Uani 1 1 d . . .
H5 H 0.3901 0.1007 0.6221 0.049 Uiso 1 1 calc R . .
C6 C 0.2928(2) 0.06948(15) 0.69810(11) 0.0362(7) Uani 1 1 d . . .
C7 C 0.1953(3) 0.12604(15) 0.68812(12) 0.0378(7) Uani 1 1 d . . .
C8 C 0.0274(2) 0.19453(15) 0.74267(12) 0.0352(6) Uani 1 1 d . . .
C9 C 0.0205(3) 0.23476(16) 0.79786(12) 0.0438(7) Uani 1 1 d . . .
H9 H 0.0817 0.2280 0.8287 0.053 Uiso 1 1 calc R . .
C10 C -0.0732(3) 0.28405(16) 0.80859(13) 0.0447(8) Uani 1 1 d . . .
H10 H -0.0772 0.3102 0.8468 0.054 Uiso 1 1 calc R . .
C11 C -0.1616(3) 0.29544(16) 0.76365(13) 0.0446(7) Uani 1 1 d . . .
H11 H -0.2256 0.3301 0.7704 0.054 Uiso 1 1 calc R . .
C12 C -0.1560(3) 0.25572(16) 0.70865(13) 0.0433(7) Uani 1 1 d . . .
H12 H -0.2159 0.2639 0.6774 0.052 Uiso 1 1 calc R . .
C13 C -0.0642(3) 0.20413(15) 0.69855(12) 0.0374(7) Uani 1 1 d . . .
C14 C -0.1615(3) 0.13311(16) 0.61414(12) 0.0393(7) Uani 1 1 d . . .
C15 C -0.1336(3) 0.10252(15) 0.55038(12) 0.0366(7) Uani 1 1 d . . .
C16 C -0.2246(3) 0.06977(16) 0.51551(12) 0.0424(7) Uani 1 1 d . . .
H16 H -0.3044 0.0635 0.5321 0.051 Uiso 1 1 calc R . .
C17 C -0.1973(3) 0.04613(16) 0.45572(13) 0.0446(7) Uani 1 1 d . . .
H17 H -0.2577 0.0227 0.4308 0.054 Uiso 1 1 calc R . .
C18 C -0.0811(3) 0.05727(16) 0.43330(13) 0.0439(7) Uani 1 1 d . . .
H18 H -0.0602 0.0421 0.3924 0.053 Uiso 1 1 calc R . .
C19 C 0.0051(3) 0.09076(15) 0.47090(12) 0.0388(7) Uani 1 1 d . . .
C20 C 0.1322(3) 0.10617(16) 0.44732(12) 0.0431(7) Uani 1 1 d . . .
C21 C 0.3323(3) 0.15602(15) 0.48060(12) 0.0392(7) Uani 1 1 d . . .
C22 C 0.3894(3) 0.19453(15) 0.52858(13) 0.0410(7) Uani 1 1 d . . .
H22 H 0.3449 0.2063 0.5652 0.049 Uiso 1 1 calc R . .
C23 C 0.5106(3) 0.21565(16) 0.52316(13) 0.0451(7) Uani 1 1 d . . .
H23 H 0.5492 0.2412 0.5564 0.054 Uiso 1 1 calc R . .
C24 C 0.5761(3) 0.19986(16) 0.46982(14) 0.0484(8) Uani 1 1 d . . .
H24 H 0.6593 0.2143 0.4662 0.058 Uiso 1 1 calc R . .
C25 C 0.5190(3) 0.16288(17) 0.42206(14) 0.0522(8) Uani 1 1 d . . .
H25 H 0.5631 0.1530 0.3850 0.063 Uiso 1 1 calc R . .
C26 C 0.3984(3) 0.13979(17) 0.42689(13) 0.0486(8) Uani 1 1 d . . .
H26 H 0.3612 0.1131 0.3939 0.058 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
O1 C7 1.239(3) . ?
O2 C14 1.233(3) . ?
O3 C20 1.222(3) . ?
N1 C7 1.355(3) . ?
N1 C8 1.427(3) . ?
N1 H1N 0.90(3) . ?
N2 C14 1.342(3) . ?
N2 C13 1.421(3) . ?
N2 H2N 0.92(3) . ?
N3 C20 1.345(4) . ?
N3 C21 1.407(4) . ?
N3 H3N 0.91(3) . ?
N4 C15 1.338(3) . ?
N4 C19 1.346(3) . ?
C1 C2 1.382(4) . ?
C1 C6 1.390(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.376(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.491(4) . ?
C8 C13 1.391(4) . ?
C8 C9 1.395(4) . ?
C9 C10 1.377(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9500 . ?
C14 C15 1.511(4) . ?
C15 C16 1.379(4) . ?
C16 C17 1.389(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.374(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.506(4) . ?
C21 C22 1.393(4) . ?
C21 C26 1.395(4) . ?
C22 C23 1.384(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.376(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 128.4(2) . . ?
C7 N1 H1N 116.4(18) . . ?
C8 N1 H1N 112.7(18) . . ?
C14 N2 C13 126.3(2) . . ?
C14 N2 H2N 118.6(17) . . ?
C13 N2 H2N 115.1(18) . . ?
C20 N3 C21 127.9(2) . . ?
C20 N3 H3N 112.3(18) . . ?
C21 N3 H3N 119.8(18) . . ?
C15 N4 C19 117.7(2) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 C7 117.9(2) . . ?
C1 C6 C7 123.6(2) . . ?
O1 C7 N1 123.0(3) . . ?
O1 C7 C6 120.9(2) . . ?
N1 C7 C6 116.1(2) . . ?
C13 C8 C9 118.6(3) . . ?
C13 C8 N1 124.7(2) . . ?
C9 C8 N1 116.6(2) . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C8 119.8(2) . . ?
C12 C13 N2 119.5(2) . . ?
C8 C13 N2 120.7(2) . . ?
O2 C14 N2 126.2(3) . . ?
O2 C14 C15 120.4(3) . . ?
N2 C14 C15 113.4(2) . . ?
N4 C15 C16 123.0(3) . . ?
N4 C15 C14 116.5(2) . . ?
C16 C15 C14 120.4(3) . . ?
C15 C16 C17 118.8(3) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 118.7(3) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 119.3(3) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
N4 C19 C18 122.6(3) . . ?
N4 C19 C20 116.6(2) . . ?
C18 C19 C20 120.8(3) . . ?
O3 C20 N3 125.3(3) . . ?
O3 C20 C19 119.5(3) . . ?
N3 C20 C19 115.2(2) . . ?
C22 C21 C26 119.2(3) . . ?
C22 C21 N3 117.7(2) . . ?
C26 C21 N3 123.1(3) . . ?
C23 C22 C21 120.3(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.6(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.0(3) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 121.4(3) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C25 C26 C21 119.5(3) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?

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
C6 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 1.8(4) . . . . ?
C2 C3 C4 C5 -2.0(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 -179.2(3) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C1 C6 C7 178.9(3) . . . . ?
C8 N1 C7 O1 -2.4(5) . . . . ?
C8 N1 C7 C6 178.1(2) . . . . ?
C5 C6 C7 O1 18.7(4) . . . . ?
C1 C6 C7 O1 -160.7(3) . . . . ?
C5 C6 C7 N1 -161.8(2) . . . . ?
C1 C6 C7 N1 18.8(4) . . . . ?
C7 N1 C8 C13 44.9(4) . . . . ?
C7 N1 C8 C9 -140.1(3) . . . . ?
C13 C8 C9 C10 -1.1(4) . . . . ?
N1 C8 C9 C10 -176.4(3) . . . . ?
C8 C9 C10 C11 -1.2(4) . . . . ?
C9 C10 C11 C12 1.3(4) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C11 C12 C13 C8 -3.3(4) . . . . ?
C11 C12 C13 N2 177.8(3) . . . . ?
C9 C8 C13 C12 3.3(4) . . . . ?
N1 C8 C13 C12 178.2(2) . . . . ?
C9 C8 C13 N2 -177.7(2) . . . . ?
N1 C8 C13 N2 -2.8(4) . . . . ?
C14 N2 C13 C12 -40.6(4) . . . . ?
C14 N2 C13 C8 140.4(3) . . . . ?
C13 N2 C14 O2 -8.7(5) . . . . ?
C13 N2 C14 C15 170.8(2) . . . . ?
C19 N4 C15 C16 1.1(4) . . . . ?
C19 N4 C15 C14 -175.3(2) . . . . ?
O2 C14 C15 N4 175.3(3) . . . . ?
N2 C14 C15 N4 -4.2(4) . . . . ?
O2 C14 C15 C16 -1.2(4) . . . . ?
N2 C14 C15 C16 179.3(2) . . . . ?
N4 C15 C16 C17 0.0(4) . . . . ?
C14 C15 C16 C17 176.3(2) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C16 C17 C18 C19 0.7(4) . . . . ?
C15 N4 C19 C18 -1.3(4) . . . . ?
C15 N4 C19 C20 177.2(2) . . . . ?
C17 C18 C19 N4 0.5(4) . . . . ?
C17 C18 C19 C20 -178.0(3) . . . . ?
C21 N3 C20 O3 2.2(5) . . . . ?
C21 N3 C20 C19 -176.9(2) . . . . ?
N4 C19 C20 O3 -172.6(3) . . . . ?
C18 C19 C20 O3 5.9(4) . . . . ?
N4 C19 C20 N3 6.5(4) . . . . ?
C18 C19 C20 N3 -174.9(3) . . . . ?
C20 N3 C21 C22 169.0(3) . . . . ?
C20 N3 C21 C26 -12.8(4) . . . . ?
C26 C21 C22 C23 -0.7(4) . . . . ?
N3 C21 C22 C23 177.6(3) . . . . ?
C21 C22 C23 C24 1.0(4) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C23 C24 C25 C26 -1.5(5) . . . . ?
C24 C25 C26 C21 1.7(5) . . . . ?
C22 C21 C26 C25 -0.6(4) . . . . ?
N3 C21 C26 C25 -178.8(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
N1 H1N O2 0.90(3) 2.12(3) 2.989(3) 163(2) 6_657
N2 H2N O1 0.92(3) 1.88(3) 2.682(3) 145(2) .
N3 H3N N4 0.91(3) 2.18(3) 2.684(3) 114(2) .
N3 H3N O1 0.91(3) 2.37(3) 3.207(3) 153(2) .
N2 H2N N4 0.92(3) 2.22(3) 2.643(3) 107(2) .

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        66.77
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.051

#===end
####################################################################### 
# 
# 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_3-Form-I-at
_database_code_depnum_ccdc_archive 'CCDC 1436667'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
N2-(2-aminophenyl)-N6-(2-benzamidophenyl)pyridine-2,6-dicarboxamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H21 N5 O3'
_chemical_formula_sum            'C26 H21 N5 O3'
_chemical_formula_weight         451.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   8.5193(3)
_cell_length_b                   9.8054(4)
_cell_length_c                   14.3709(4)
_cell_angle_alpha                74.437(3)
_cell_angle_beta                 75.224(3)
_cell_angle_gamma                78.208(3)
_cell_volume                     1106.25(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9404
_cell_measurement_theta_min      2.1690
_cell_measurement_theta_max      28.9170

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_T_min  0.81216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            23956
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.1794
_diffrn_reflns_theta_max         29.2849
_diffrn_measured_fraction_theta_max 0.9038
_diffrn_reflns_theta_full        26.3154
_diffrn_measured_fraction_theta_full 0.9998
_reflns_number_total             5460
_reflns_number_gt                4446
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0319P)²+0.6052P] 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         5460
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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 0.75636(14) 0.15796(11) 0.12218(8) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.35670(13) 0.30808(11) -0.09864(7) 0.0277(2) Uani 1 1 d . . . . .
O3 O 0.37856(16) -0.24016(13) 0.32836(8) 0.0399(3) Uani 1 1 d . . . . .
N1 N 0.73124(16) 0.40057(14) 0.08041(9) 0.0262(3) Uani 1 1 d . . . . .
H1N H 0.727(2) 0.477(2) 0.1011(13) 0.031 Uiso 1 1 d . U . . .
N2 N 0.56060(15) 0.26322(13) -0.01212(9) 0.0239(3) Uani 1 1 d . . . . .
H2N H 0.595(2) 0.2082(19) 0.0405(13) 0.029 Uiso 1 1 d . U . . .
N3 N 0.57515(16) -0.09577(14) 0.26796(9) 0.0271(3) Uani 1 1 d . . . . .
H3N H 0.610(2) -0.022(2) 0.2210(13) 0.033 Uiso 1 1 d . U . . .
N4 N 0.41898(14) 0.05073(13) 0.11971(8) 0.0228(2) Uani 1 1 d . . . . .
N5 N 0.87507(18) -0.26769(17) 0.21989(10) 0.0338(3) Uani 1 1 d . . . . .
H5NA H 0.796(3) -0.264(2) 0.1878(14) 0.041 Uiso 1 1 d . U . . .
H5NB H 0.956(3) -0.343(2) 0.2145(14) 0.041 Uiso 1 1 d . U . . .
C1 C 0.8199(2) 0.1562(2) 0.30571(12) 0.0376(4) Uani 1 1 d . . . . .
H1 H 0.8618 0.0725 0.2807 0.045 Uiso 1 1 calc R U . . .
C2 C 0.8311(3) 0.1577(2) 0.40011(14) 0.0498(5) Uani 1 1 d . . . . .
H2 H 0.8830 0.0752 0.4393 0.060 Uiso 1 1 calc R U . . .
C3 C 0.7677(3) 0.2776(3) 0.43743(13) 0.0518(5) Uani 1 1 d . . . . .
H3 H 0.7752 0.2773 0.5023 0.062 Uiso 1 1 calc R U . . .
C4 C 0.6932(3) 0.3982(2) 0.38098(13) 0.0464(5) Uani 1 1 d . . . . .
H4 H 0.6485 0.4805 0.4072 0.056 Uiso 1 1 calc R U . . .
C5 C 0.6836(2) 0.39933(19) 0.28580(12) 0.0359(4) Uani 1 1 d . . . . .
H5 H 0.6338 0.4830 0.2465 0.043 Uiso 1 1 calc R U . . .
C6 C 0.74651(19) 0.27840(17) 0.24789(11) 0.0290(3) Uani 1 1 d . . . . .
C7 C 0.74356(17) 0.27230(16) 0.14551(11) 0.0257(3) Uani 1 1 d . . . . .
C8 C 0.74264(17) 0.43040(15) -0.02333(10) 0.0235(3) Uani 1 1 d . . . . .
C9 C 0.83593(18) 0.53738(17) -0.08026(11) 0.0285(3) Uani 1 1 d . . . . .
H9 H 0.8971 0.5765 -0.0496 0.034 Uiso 1 1 calc R U . . .
C10 C 0.84110(19) 0.58744(17) -0.18032(12) 0.0320(3) Uani 1 1 d . . . . .
H10 H 0.9021 0.6625 -0.2178 0.038 Uiso 1 1 calc R U . . .
C12 C 0.66757(18) 0.41777(17) -0.17073(11) 0.0279(3) Uani 1 1 d . . . . .
H12 H 0.6131 0.3747 -0.2030 0.033 Uiso 1 1 calc R U . . .
C11 C 0.7563(2) 0.52677(18) -0.22524(11) 0.0316(3) Uani 1 1 d . . . . .
H11 H 0.7591 0.5603 -0.2940 0.038 Uiso 1 1 calc R U . . .
C17 C 0.11686(19) -0.00933(17) 0.11262(12) 0.0312(3) Uani 1 1 d . . . . .
H17 H 0.0140 -0.0300 0.1102 0.037 Uiso 1 1 calc R U . . .
C16 C 0.19164(18) 0.09559(16) 0.04025(11) 0.0282(3) Uani 1 1 d . . . . .
H16 H 0.1417 0.1483 -0.0132 0.034 Uiso 1 1 calc R U . . .
C15 C 0.34104(17) 0.12252(15) 0.04713(10) 0.0229(3) Uani 1 1 d . . . . .
C14 C 0.42146(17) 0.23959(15) -0.02882(10) 0.0228(3) Uani 1 1 d . . . . .
C13 C 0.65666(17) 0.36987(15) -0.06901(10) 0.0233(3) Uani 1 1 d . . . . .
C18 C 0.19447(19) -0.08384(17) 0.18884(11) 0.0290(3) Uani 1 1 d . . . . .
H18 H 0.1453 -0.1558 0.2402 0.035 Uiso 1 1 calc R U . . .
C19 C 0.34570(18) -0.05133(16) 0.18874(10) 0.0242(3) Uani 1 1 d . . . . .
C20 C 0.43444(19) -0.13779(16) 0.26874(10) 0.0265(3) Uani 1 1 d . . . . .
C21 C 0.66891(19) -0.16515(16) 0.34174(11) 0.0274(3) Uani 1 1 d . . . . .
C22 C 0.81800(19) -0.24986(16) 0.31613(11) 0.0280(3) Uani 1 1 d . . . . .
C23 C 0.9103(2) -0.31048(19) 0.38878(12) 0.0359(4) Uani 1 1 d . . . . .
H23 H 1.0148 -0.3654 0.3725 0.043 Uiso 1 1 calc R U . . .
C24 C 0.8514(2) -0.2914(2) 0.48360(13) 0.0426(4) Uani 1 1 d . . . . .
H24 H 0.9157 -0.3333 0.5320 0.051 Uiso 1 1 calc R U . . .
C25 C 0.7006(2) -0.2122(2) 0.50915(13) 0.0457(5) Uani 1 1 d . . . . .
H25 H 0.6595 -0.2015 0.5751 0.055 Uiso 1 1 calc R U . . .
C26 C 0.6091(2) -0.1485(2) 0.43764(12) 0.0372(4) Uani 1 1 d . . . . .
H26 H 0.5051 -0.0932 0.4545 0.045 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 C7 1.2306(18) . ?
O2 C14 1.2376(16) . ?
O3 C20 1.2223(18) . ?
N1 C7 1.3538(19) . ?
N1 C8 1.4218(18) . ?
N1 H1N 0.874(19) . ?
N2 C14 1.3430(18) . ?
N2 C13 1.4076(18) . ?
N2 H2N 0.881(18) . ?
N3 C20 1.3415(19) . ?
N3 C21 1.4311(18) . ?
N3 H3N 0.888(19) . ?
N4 C19 1.3350(18) . ?
N4 C15 1.3388(17) . ?
N5 C22 1.390(2) . ?
N5 H5NA 0.90(2) . ?
N5 H5NB 0.91(2) . ?
C1 C2 1.388(2) . ?
C1 C6 1.393(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.376(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.495(2) . ?
C8 C9 1.396(2) . ?
C8 C13 1.397(2) . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(2) . ?
C10 H10 0.9500 . ?
C12 C11 1.381(2) . ?
C12 C13 1.3950(19) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C17 C16 1.379(2) . ?
C17 C18 1.383(2) . ?
C17 H17 0.9500 . ?
C16 C15 1.384(2) . ?
C16 H16 0.9500 . ?
C15 C14 1.499(2) . ?
C18 C19 1.389(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.507(2) . ?
C21 C26 1.384(2) . ?
C21 C22 1.390(2) . ?
C22 C23 1.399(2) . ?
C23 C24 1.376(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.376(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 129.00(13) . . ?
C7 N1 H1N 118.2(12) . . ?
C8 N1 H1N 112.3(12) . . ?
C14 N2 C13 126.62(12) . . ?
C14 N2 H2N 117.3(11) . . ?
C13 N2 H2N 116.1(11) . . ?
C20 N3 C21 121.64(13) . . ?
C20 N3 H3N 119.0(12) . . ?
C21 N3 H3N 119.3(12) . . ?
C19 N4 C15 117.06(12) . . ?
C22 N5 H5NA 114.5(13) . . ?
C22 N5 H5NB 113.3(12) . . ?
H5NA N5 H5NB 113.7(17) . . ?
C2 C1 C6 119.47(18) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C3 C2 C1 120.54(18) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.22(17) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.13(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.69(15) . . ?
C5 C6 C7 123.23(14) . . ?
C1 C6 C7 117.07(15) . . ?
O1 C7 N1 122.88(14) . . ?
O1 C7 C6 121.86(13) . . ?
N1 C7 C6 115.23(13) . . ?
C9 C8 C13 119.34(13) . . ?
C9 C8 N1 115.85(13) . . ?
C13 C8 N1 124.55(13) . . ?
C10 C9 C8 121.30(14) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 119.09(14) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C11 C12 C13 121.00(14) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C11 C10 120.40(14) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C16 C17 C18 118.73(14) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C17 C16 C15 118.61(14) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
N4 C15 C16 123.62(13) . . ?
N4 C15 C14 116.96(12) . . ?
C16 C15 C14 119.42(13) . . ?
O2 C14 N2 125.23(13) . . ?
O2 C14 C15 119.93(13) . . ?
N2 C14 C15 114.81(12) . . ?
C12 C13 C8 118.79(13) . . ?
C12 C13 N2 121.40(13) . . ?
C8 C13 N2 119.81(12) . . ?
C17 C18 C19 118.68(14) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
N4 C19 C18 123.29(13) . . ?
N4 C19 C20 118.00(12) . . ?
C18 C19 C20 118.68(13) . . ?
O3 C20 N3 124.08(14) . . ?
O3 C20 C19 120.14(13) . . ?
N3 C20 C19 115.77(13) . . ?
C26 C21 C22 120.97(14) . . ?
C26 C21 N3 119.63(15) . . ?
C22 C21 N3 119.40(13) . . ?
N5 C22 C21 120.32(13) . . ?
N5 C22 C23 121.68(15) . . ?
C21 C22 C23 117.94(15) . . ?
C24 C23 C22 120.69(16) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 120.82(15) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 119.31(17) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C21 C26 C25 120.16(17) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?

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
C6 C1 C2 C3 1.3(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C4 C5 C6 C7 -178.82(15) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C2 C1 C6 C7 177.76(15) . . . . ?
C8 N1 C7 O1 -5.3(2) . . . . ?
C8 N1 C7 C6 172.68(13) . . . . ?
C5 C6 C7 O1 -159.42(15) . . . . ?
C1 C6 C7 O1 22.0(2) . . . . ?
C5 C6 C7 N1 22.6(2) . . . . ?
C1 C6 C7 N1 -156.00(14) . . . . ?
C7 N1 C8 C9 -136.38(16) . . . . ?
C7 N1 C8 C13 49.5(2) . . . . ?
C13 C8 C9 C10 1.9(2) . . . . ?
N1 C8 C9 C10 -172.56(14) . . . . ?
C8 C9 C10 C11 -2.1(2) . . . . ?
C13 C12 C11 C10 2.2(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C18 C17 C16 C15 -0.3(2) . . . . ?
C19 N4 C15 C16 -0.4(2) . . . . ?
C19 N4 C15 C14 178.46(12) . . . . ?
C17 C16 C15 N4 1.0(2) . . . . ?
C17 C16 C15 C14 -177.87(14) . . . . ?
C13 N2 C14 O2 1.0(2) . . . . ?
C13 N2 C14 C15 -177.19(13) . . . . ?
N4 C15 C14 O2 178.75(13) . . . . ?
C16 C15 C14 O2 -2.3(2) . . . . ?
N4 C15 C14 N2 -2.99(19) . . . . ?
C16 C15 C14 N2 175.96(13) . . . . ?
C11 C12 C13 C8 -2.5(2) . . . . ?
C11 C12 C13 N2 177.15(14) . . . . ?
C9 C8 C13 C12 0.4(2) . . . . ?
N1 C8 C13 C12 174.34(14) . . . . ?
C9 C8 C13 N2 -179.20(13) . . . . ?
N1 C8 C13 N2 -5.3(2) . . . . ?
C14 N2 C13 C12 -31.6(2) . . . . ?
C14 N2 C13 C8 147.97(14) . . . . ?
C16 C17 C18 C19 -0.8(2) . . . . ?
C15 N4 C19 C18 -0.8(2) . . . . ?
C15 N4 C19 C20 177.44(13) . . . . ?
C17 C18 C19 N4 1.5(2) . . . . ?
C17 C18 C19 C20 -176.78(14) . . . . ?
C21 N3 C20 O3 -3.2(2) . . . . ?
C21 N3 C20 C19 177.77(13) . . . . ?
N4 C19 C20 O3 -173.69(14) . . . . ?
C18 C19 C20 O3 4.7(2) . . . . ?
N4 C19 C20 N3 5.4(2) . . . . ?
C18 C19 C20 N3 -176.24(14) . . . . ?
C20 N3 C21 C26 -70.1(2) . . . . ?
C20 N3 C21 C22 109.13(17) . . . . ?
C26 C21 C22 N5 178.83(15) . . . . ?
N3 C21 C22 N5 -0.4(2) . . . . ?
C26 C21 C22 C23 -3.9(2) . . . . ?
N3 C21 C22 C23 176.95(14) . . . . ?
N5 C22 C23 C24 179.96(16) . . . . ?
C21 C22 C23 C24 2.7(2) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C24 C25 C26 -1.6(3) . . . . ?
C22 C21 C26 C25 2.4(3) . . . . ?
N3 C21 C26 C25 -178.43(16) . . . . ?
C24 C25 C26 C21 0.4(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
N1 H1N O2 0.874(19) 2.072(19) 2.8667(17) 150.8(16) 2_665
N2 H2N O1 0.881(18) 1.938(18) 2.7279(15) 148.4(16) .
N3 H3N O1 0.888(19) 2.311(19) 3.1757(17) 164.4(16) .
N5 H5NA O2 0.90(2) 2.21(2) 3.0881(17) 164.2(17) 2_655

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_7-CHCl3-S1
_database_code_depnum_ccdc_archive 'CCDC 1436668'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H24 N6 O4, C H Cl3'
_chemical_formula_sum            'C35 H25 Cl3 N6 O4'
_chemical_formula_weight         699.96

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.3983(2)
_cell_length_b                   19.7518(3)
_cell_length_c                   14.0691(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.8562(16)
_cell_angle_gamma                90
_cell_volume                     3394.52(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6548
_cell_measurement_theta_min      2.2640
_cell_measurement_theta_max      28.8400

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.318
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_T_min  0.98851
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            13725
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.7948
_diffrn_reflns_theta_max         29.1575
_diffrn_measured_fraction_theta_max 0.8410
_diffrn_reflns_theta_full        26.3154
_diffrn_measured_fraction_theta_full 0.9912
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7694
_reflns_number_gt                6057
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+2.5029P] 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         7694
_refine_ls_number_parameters     476
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.16248(12) 0.39956(7) 0.63761(10) 0.0396(3) Uani 1 1 d . . . . .
O2 O 0.28077(13) 0.21777(7) 0.87520(9) 0.0396(4) Uani 1 1 d . . . . .
O3 O 0.52152(10) -0.06869(6) 0.70244(9) 0.0287(3) Uani 1 1 d . . . . .
O4 O 0.22716(11) 0.08550(7) 0.54111(9) 0.0306(3) Uani 1 1 d . . . . .
N1 N 0.19342(13) 0.31220(8) 0.74358(11) 0.0302(3) Uani 1 1 d D . . . .
H1N H 0.2356(18) 0.2947(12) 0.7909(14) 0.045 Uiso 1 1 d D U . . .
N2 N 0.22058(13) 0.16778(8) 0.72910(11) 0.0298(3) Uani 1 1 d D . . . .
H2N H 0.2343(19) 0.1343(10) 0.6944(15) 0.045 Uiso 1 1 d D U . . .
N3 N 0.37424(12) -0.01229(8) 0.61820(10) 0.0263(3) Uani 1 1 d D . . . .
H3N H 0.3340(17) 0.0219(9) 0.6197(16) 0.040 Uiso 1 1 d D U . . .
N4 N 0.33691(13) 0.05595(8) 0.43412(11) 0.0275(3) Uani 1 1 d D . . . .
H4N H 0.3723(18) 0.0694(11) 0.3908(14) 0.041 Uiso 1 1 d D U . . .
N5 N 0.37661(12) 0.07531(7) 0.76150(10) 0.0258(3) Uani 1 1 d . . . . .
N6 N 0.3397(2) 0.44078(11) 0.3916(2) 0.0763(8) Uani 1 1 d . . . . .
C1 C 0.37907(18) 0.38580(11) 0.84727(15) 0.0396(5) Uani 1 1 d . . . . .
H1 H 0.3522 0.3495 0.8809 0.048 Uiso 1 1 calc R U . . .
C2 C 0.4752(2) 0.41803(13) 0.88722(18) 0.0502(6) Uani 1 1 d . . . . .
H2 H 0.5136 0.4039 0.9483 0.060 Uiso 1 1 calc R U . . .
C3 C 0.5157(2) 0.47060(13) 0.8389(2) 0.0525(6) Uani 1 1 d . . . . .
H3 H 0.5822 0.4923 0.8663 0.063 Uiso 1 1 calc R U . . .
C4 C 0.4590(2) 0.49146(11) 0.75026(18) 0.0477(6) Uani 1 1 d . . . . .
H4 H 0.4867 0.5275 0.7167 0.057 Uiso 1 1 calc R U . . .
C5 C 0.36199(19) 0.45994(10) 0.71045(16) 0.0397(5) Uani 1 1 d . . . . .
H5 H 0.3228 0.4751 0.6502 0.048 Uiso 1 1 calc R U . . .
C6 C 0.32137(16) 0.40621(10) 0.75798(14) 0.0316(4) Uani 1 1 d . . . . .
C7 C 0.21854(16) 0.37327(10) 0.70780(13) 0.0299(4) Uani 1 1 d . . . . .
C8 C 0.10432(15) 0.27092(9) 0.70292(12) 0.0277(4) Uani 1 1 d . . . . .
C9 C 0.00145(16) 0.29793(10) 0.66586(14) 0.0331(4) Uani 1 1 d . . . . .
H9 H -0.0108 0.3451 0.6714 0.040 Uiso 1 1 calc R U . . .
C10 C -0.08256(16) 0.25701(11) 0.62130(15) 0.0374(5) Uani 1 1 d . . . . .
H10 H -0.1516 0.2763 0.5957 0.045 Uiso 1 1 calc R U . . .
C11 C -0.06640(17) 0.18794(11) 0.61385(15) 0.0377(5) Uani 1 1 d . . . . .
H11 H -0.1238 0.1599 0.5822 0.045 Uiso 1 1 calc R U . . .
C12 C 0.03363(16) 0.16004(10) 0.65274(14) 0.0339(4) Uani 1 1 d . . . . .
H12 H 0.0443 0.1126 0.6487 0.041 Uiso 1 1 calc R U . . .
C13 C 0.11905(15) 0.20077(9) 0.69774(13) 0.0280(4) Uani 1 1 d . . . . .
C14 C 0.28834(16) 0.17400(9) 0.81426(13) 0.0299(4) Uani 1 1 d . . . . .
C15 C 0.37675(16) 0.12114(9) 0.83143(13) 0.0286(4) Uani 1 1 d . . . . .
C16 C 0.45178(17) 0.12039(10) 0.91674(14) 0.0347(4) Uani 1 1 d . . . . .
H16 H 0.4496 0.1540 0.9647 0.042 Uiso 1 1 calc R U . . .
C17 C 0.52996(17) 0.06963(10) 0.93040(14) 0.0350(4) Uani 1 1 d . . . . .
H17 H 0.5821 0.0676 0.9883 0.042 Uiso 1 1 calc R U . . .
C18 C 0.53093(16) 0.02211(10) 0.85864(13) 0.0303(4) Uani 1 1 d . . . . .
H18 H 0.5839 -0.0131 0.8660 0.036 Uiso 1 1 calc R U . . .
C19 C 0.45286(14) 0.02694(9) 0.77549(12) 0.0246(3) Uani 1 1 d . . . . .
C20 C 0.45244(14) -0.02319(9) 0.69530(12) 0.0241(3) Uani 1 1 d . . . . .
C21 C 0.35913(14) -0.04980(9) 0.53141(12) 0.0247(4) Uani 1 1 d . . . . .
C22 C 0.36651(15) -0.12025(9) 0.53249(14) 0.0291(4) Uani 1 1 d . . . . .
H22 H 0.3786 -0.1436 0.5924 0.035 Uiso 1 1 calc R U . . .
C23 C 0.35643(16) -0.15648(10) 0.44751(14) 0.0342(4) Uani 1 1 d . . . . .
H23 H 0.3642 -0.2043 0.4492 0.041 Uiso 1 1 calc R U . . .
C24 C 0.33502(17) -0.12301(10) 0.35982(14) 0.0351(4) Uani 1 1 d . . . . .
H24 H 0.3279 -0.1479 0.3013 0.042 Uiso 1 1 calc R U . . .
C25 C 0.32401(16) -0.05334(10) 0.35763(13) 0.0310(4) Uani 1 1 d . . . . .
H25 H 0.3074 -0.0307 0.2973 0.037 Uiso 1 1 calc R U . . .
C26 C 0.33696(14) -0.01600(9) 0.44291(12) 0.0253(4) Uani 1 1 d . . . . .
C27 C 0.28298(14) 0.10158(9) 0.47984(12) 0.0261(4) Uani 1 1 d . . . . .
C28 C 0.29513(15) 0.17477(9) 0.45340(12) 0.0279(4) Uani 1 1 d . . . . .
C29 C 0.22794(19) 0.22137(10) 0.48871(15) 0.0387(5) Uani 1 1 d . . . . .
H29 H 0.1748 0.2059 0.5250 0.046 Uiso 1 1 calc R U . . .
C30 C 0.2373(2) 0.28984(11) 0.47190(16) 0.0438(5) Uani 1 1 d . . . . .
H30 H 0.1916 0.3213 0.4971 0.053 Uiso 1 1 calc R U . . .
C31 C 0.31410(18) 0.31226(10) 0.41773(15) 0.0377(5) Uani 1 1 d . . . . .
C32 C 0.37976(18) 0.26627(10) 0.37926(16) 0.0393(5) Uani 1 1 d . . . . .
H32 H 0.4308 0.2816 0.3408 0.047 Uiso 1 1 calc R U . . .
C33 C 0.37006(16) 0.19773(10) 0.39762(15) 0.0344(4) Uani 1 1 d . . . . .
H33 H 0.4151 0.1661 0.3718 0.041 Uiso 1 1 calc R U . . .
C34 C 0.3281(2) 0.38397(12) 0.40286(19) 0.0506(6) Uani 1 1 d . . . . .
Cl1A Cl 0.63744(11) 0.37148(13) 0.49197(12) 0.0869(7) Uani 0.737(5) 1 d . . P A
1
Cl2A Cl 0.52565(15) 0.32738(8) 0.63688(12) 0.0797(6) Uani 0.737(5) 1 d . . P A
1
Cl3A Cl 0.74018(14) 0.39537(7) 0.68458(14) 0.0604(4) Uani 0.737(5) 1 d . . P A
1
C10A C 0.6130(8) 0.3885(3) 0.6084(7) 0.0516(12) Uani 0.737(5) 1 d . . P A 1
H10A H 0.5751 0.4333 0.6073 0.062 Uiso 0.737(5) 1 calc R U P A 1
Cl1B Cl 0.6566(11) 0.4068(4) 0.4928(6) 0.189(5) Uani 0.263(5) 1 d . . P A 2
Cl2B Cl 0.5446(9) 0.3315(6) 0.6220(15) 0.391(14) Uani 0.263(5) 1 d D . P A 2
Cl3B Cl 0.7089(7) 0.3795(6) 0.7064(6) 0.149(4) Uani 0.263(5) 1 d D . P A 2
C10B C 0.617(2) 0.4044(12) 0.601(2) 0.0516(12) Uani 0.263(5) 1 d D . P A 2
H10B H 0.5757 0.4463 0.6129 0.062 Uiso 0.263(5) 1 calc R U P A 2


_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 C7 1.222(2) . ?
O2 C14 1.232(2) . ?
O3 C20 1.234(2) . ?
O4 C27 1.236(2) . ?
N1 C7 1.364(2) . ?
N1 C8 1.413(2) . ?
N1 H1N 0.847(16) . ?
N2 C14 1.346(2) . ?
N2 C13 1.419(2) . ?
N2 H2N 0.855(16) . ?
N3 C20 1.343(2) . ?
N3 C21 1.413(2) . ?
N3 H3N 0.843(16) . ?
N4 C27 1.349(2) . ?
N4 C26 1.427(2) . ?
N4 H4N 0.852(16) . ?
N5 C19 1.335(2) . ?
N5 C15 1.337(2) . ?
N6 C34 1.146(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.395(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.496(3) . ?
C8 C9 1.398(3) . ?
C8 C13 1.401(3) . ?
C9 C10 1.381(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.503(3) . ?
C15 C16 1.387(3) . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.501(2) . ?
C21 C22 1.394(2) . ?
C21 C26 1.398(2) . ?
C22 C23 1.381(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(2) . ?
C25 H25 0.9500 . ?
C27 C28 1.507(3) . ?
C28 C29 1.389(3) . ?
C28 C33 1.391(3) . ?
C29 C30 1.381(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.390(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.390(3) . ?
C31 C34 1.447(3) . ?
C32 C33 1.387(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
Cl1A C10A 1.748(12) . ?
Cl2A C10A 1.715(8) . ?
Cl3A C10A 1.754(7) . ?
C10A H10A 1.0000 . ?
Cl1B C10B 1.68(4) . ?
Cl2B C10B 1.747(18) . ?
Cl3B C10B 1.778(19) . ?
C10B H10B 1.0000 . ?

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
C7 N1 C8 124.97(16) . . ?
C7 N1 H1N 120.1(17) . . ?
C8 N1 H1N 114.7(17) . . ?
C14 N2 C13 128.32(16) . . ?
C14 N2 H2N 115.0(16) . . ?
C13 N2 H2N 115.5(16) . . ?
C20 N3 C21 125.77(15) . . ?
C20 N3 H3N 117.2(15) . . ?
C21 N3 H3N 116.8(15) . . ?
C27 N4 C26 128.10(16) . . ?
C27 N4 H4N 119.3(16) . . ?
C26 N4 H4N 112.4(16) . . ?
C19 N5 C15 117.68(16) . . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 116.96(18) . . ?
C1 C6 C7 124.30(18) . . ?
O1 C7 N1 122.69(18) . . ?
O1 C7 C6 121.16(18) . . ?
N1 C7 C6 116.14(16) . . ?
C9 C8 C13 118.46(18) . . ?
C9 C8 N1 122.06(17) . . ?
C13 C8 N1 119.46(16) . . ?
C10 C9 C8 120.98(18) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.20(19) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.63(19) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.72(19) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 119.93(17) . . ?
C12 C13 N2 116.18(17) . . ?
C8 C13 N2 123.67(17) . . ?
O2 C14 N2 124.97(18) . . ?
O2 C14 C15 121.04(17) . . ?
N2 C14 C15 113.98(16) . . ?
N5 C15 C16 123.09(17) . . ?
N5 C15 C14 116.30(16) . . ?
C16 C15 C14 120.60(17) . . ?
C17 C16 C15 118.53(18) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C18 C17 C16 118.97(18) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 118.53(18) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
N5 C19 C18 123.20(17) . . ?
N5 C19 C20 116.76(15) . . ?
C18 C19 C20 120.03(16) . . ?
O3 C20 N3 125.30(16) . . ?
O3 C20 C19 120.43(15) . . ?
N3 C20 C19 114.25(15) . . ?
C22 C21 C26 119.26(16) . . ?
C22 C21 N3 121.00(16) . . ?
C26 C21 N3 119.74(16) . . ?
C23 C22 C21 120.78(18) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 119.95(18) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 119.89(18) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.72(18) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C21 119.35(17) . . ?
C25 C26 N4 117.01(16) . . ?
C21 C26 N4 123.37(16) . . ?
O4 C27 N4 122.91(17) . . ?
O4 C27 C28 120.69(16) . . ?
N4 C27 C28 116.39(16) . . ?
C29 C28 C33 119.02(18) . . ?
C29 C28 C27 117.12(17) . . ?
C33 C28 C27 123.84(16) . . ?
C30 C29 C28 120.97(19) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C31 119.41(19) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C32 C31 C30 120.48(19) . . ?
C32 C31 C34 119.4(2) . . ?
C30 C31 C34 120.1(2) . . ?
C33 C32 C31 119.35(19) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C32 C33 C28 120.73(18) . . ?
C32 C33 H33 119.6 . . ?
C28 C33 H33 119.6 . . ?
N6 C34 C31 179.6(4) . . ?
Cl2A C10A Cl1A 107.5(4) . . ?
Cl2A C10A Cl3A 116.7(4) . . ?
Cl1A C10A Cl3A 107.8(7) . . ?
Cl2A C10A H10A 108.2 . . ?
Cl1A C10A H10A 108.2 . . ?
Cl3A C10A H10A 108.2 . . ?
Cl1B C10B Cl2B 114.4(18) . . ?
Cl1B C10B Cl3B 121(2) . . ?
Cl2B C10B Cl3B 84.6(10) . . ?
Cl1B C10B H10B 111.4 . . ?
Cl2B C10B H10B 111.4 . . ?
Cl3B C10B H10B 111.4 . . ?

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
C6 C1 C2 C3 -0.4(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C4 C5 C6 C7 -177.51(18) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C1 C6 C7 178.2(2) . . . . ?
C8 N1 C7 O1 2.8(3) . . . . ?
C8 N1 C7 C6 -175.64(16) . . . . ?
C5 C6 C7 O1 -12.8(3) . . . . ?
C1 C6 C7 O1 168.40(19) . . . . ?
C5 C6 C7 N1 165.64(17) . . . . ?
C1 C6 C7 N1 -13.1(3) . . . . ?
C7 N1 C8 C9 -40.5(3) . . . . ?
C7 N1 C8 C13 138.43(18) . . . . ?
C13 C8 C9 C10 -2.8(3) . . . . ?
N1 C8 C9 C10 176.11(18) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C11 C12 C13 C8 -0.7(3) . . . . ?
C11 C12 C13 N2 -175.67(17) . . . . ?
C9 C8 C13 C12 2.7(3) . . . . ?
N1 C8 C13 C12 -176.25(16) . . . . ?
C9 C8 C13 N2 177.25(16) . . . . ?
N1 C8 C13 N2 -1.7(3) . . . . ?
C14 N2 C13 C12 -134.6(2) . . . . ?
C14 N2 C13 C8 50.7(3) . . . . ?
C13 N2 C14 O2 -11.4(3) . . . . ?
C13 N2 C14 C15 167.77(17) . . . . ?
C19 N5 C15 C16 -0.1(3) . . . . ?
C19 N5 C15 C14 -178.74(16) . . . . ?
O2 C14 C15 N5 178.89(18) . . . . ?
N2 C14 C15 N5 -0.3(2) . . . . ?
O2 C14 C15 C16 0.2(3) . . . . ?
N2 C14 C15 C16 -178.99(18) . . . . ?
N5 C15 C16 C17 -0.3(3) . . . . ?
C14 C15 C16 C17 178.30(18) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C15 N5 C19 C18 0.3(3) . . . . ?
C15 N5 C19 C20 -178.90(15) . . . . ?
C17 C18 C19 N5 -0.1(3) . . . . ?
C17 C18 C19 C20 179.07(17) . . . . ?
C21 N3 C20 O3 -1.6(3) . . . . ?
C21 N3 C20 C19 176.77(15) . . . . ?
N5 C19 C20 O3 178.88(16) . . . . ?
C18 C19 C20 O3 -0.3(3) . . . . ?
N5 C19 C20 N3 0.4(2) . . . . ?
C18 C19 C20 N3 -178.81(16) . . . . ?
C20 N3 C21 C22 43.2(3) . . . . ?
C20 N3 C21 C26 -136.47(18) . . . . ?
C26 C21 C22 C23 2.5(3) . . . . ?
N3 C21 C22 C23 -177.15(17) . . . . ?
C21 C22 C23 C24 -2.2(3) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C23 C24 C25 C26 1.6(3) . . . . ?
C24 C25 C26 C21 -1.3(3) . . . . ?
C24 C25 C26 N4 172.89(18) . . . . ?
C22 C21 C26 C25 -0.8(3) . . . . ?
N3 C21 C26 C25 178.92(16) . . . . ?
C22 C21 C26 N4 -174.57(17) . . . . ?
N3 C21 C26 N4 5.1(3) . . . . ?
C27 N4 C26 C25 134.34(19) . . . . ?
C27 N4 C26 C21 -51.7(3) . . . . ?
C26 N4 C27 O4 3.0(3) . . . . ?
C26 N4 C27 C28 -177.83(16) . . . . ?
O4 C27 C28 C29 -10.0(3) . . . . ?
N4 C27 C28 C29 170.77(17) . . . . ?
O4 C27 C28 C33 169.00(18) . . . . ?
N4 C27 C28 C33 -10.2(3) . . . . ?
C33 C28 C29 C30 -2.2(3) . . . . ?
C27 C28 C29 C30 176.86(19) . . . . ?
C28 C29 C30 C31 0.9(3) . . . . ?
C29 C30 C31 C32 1.1(3) . . . . ?
C29 C30 C31 C34 -177.4(2) . . . . ?
C30 C31 C32 C33 -1.8(3) . . . . ?
C34 C31 C32 C33 176.8(2) . . . . ?
C31 C32 C33 C28 0.4(3) . . . . ?
C29 C28 C33 C32 1.6(3) . . . . ?
C27 C28 C33 C32 -177.42(19) . . . . ?

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 O2 0.847(16) 1.950(19) 2.719(2) 151(2) .
N2 H2N O4 0.855(16) 2.351(18) 3.117(2) 149(2) .
N2 H2N N5 0.855(16) 2.19(2) 2.643(2) 112.9(19) .
N3 H3N O4 0.843(16) 2.013(18) 2.7488(19) 145(2) .
N3 H3N N5 0.843(16) 2.24(2) 2.653(2) 110.4(17) .
N4 H4N O3 0.852(16) 2.012(17) 2.827(2) 160(2) 3_656

_refine_diff_density_max         0.641
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.048

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_7-DMA-S1
_database_code_depnum_ccdc_archive 'CCDC 1436669'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H24 N6 O4, C4 H9 N O'
_chemical_formula_sum            'C38 H33 N7 O5'
_chemical_formula_weight         667.71

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   12.1856(5)
_cell_length_b                   20.3897(8)
_cell_length_c                   13.7195(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.426(3)
_cell_angle_gamma                90.00
_cell_volume                     3393.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8682
_exptl_absorpt_correction_T_max  0.9178
_exptl_absorpt_process_details   
;
Denzo (otwinowski, Borek, Majewski & Minor, 2003) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KappaCCD, Cu, APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9461
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_sigmaI/netI    0.0897
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.90
_diffrn_reflns_theta_max         66.77
_reflns_number_total             5424
_reflns_number_gt                3186
_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)+(0.0744P)²+2.7061P] 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         5424
_refine_ls_number_parameters     466
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.2001
_refine_ls_wR_factor_gt          0.1653
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1740(3) 0.60883(14) 0.6265(2) 0.0563(8) Uani 1 1 d . . .
O2 O 0.2606(3) 0.78340(13) 0.8779(2) 0.0609(9) Uani 1 1 d . . .
O3 O 0.5051(2) 1.06618(13) 0.70165(19) 0.0480(7) Uani 1 1 d . . .
O4 O 0.2151(2) 0.91745(13) 0.54565(19) 0.0448(7) Uani 1 1 d . . .
N1 N 0.1902(3) 0.69082(16) 0.7386(3) 0.0466(9) Uani 1 1 d . . .
H1N H 0.228(4) 0.707(2) 0.783(3) 0.056 Uiso 1 1 d . . .
N2 N 0.2071(3) 0.83208(16) 0.7305(2) 0.0431(8) Uani 1 1 d . . .
H2N H 0.214(3) 0.870(2) 0.693(3) 0.052 Uiso 1 1 d . . .
N3 N 0.3663(3) 1.00947(16) 0.6150(2) 0.0420(8) Uani 1 1 d . . .
H3N H 0.321(3) 0.977(2) 0.615(3) 0.050 Uiso 1 1 d . . .
N4 N 0.3233(3) 0.94519(17) 0.4269(3) 0.0484(10) Uani 1 1 d . . .
H4N H 0.347(4) 0.936(2) 0.379(3) 0.058 Uiso 1 1 d . . .
N5 N 0.3611(3) 0.92338(14) 0.7608(2) 0.0385(8) Uani 1 1 d . . .
N6 N 0.3235(5) 0.5758(2) 0.3718(4) 0.1046(18) Uani 1 1 d . . .
C1 C 0.3709(4) 0.5501(2) 0.7031(4) 0.0667(14) Uani 1 1 d . . .
H1 H 0.3410 0.5377 0.6393 0.080 Uiso 1 1 calc R . .
C2 C 0.4621(5) 0.5178(2) 0.7467(4) 0.0795(16) Uani 1 1 d . . .
H2 H 0.4959 0.4843 0.7120 0.095 Uiso 1 1 calc R . .
C3 C 0.5049(5) 0.5341(2) 0.8410(4) 0.0765(15) Uani 1 1 d . . .
H3 H 0.5664 0.5110 0.8717 0.092 Uiso 1 1 calc R . .
C4 C 0.4572(4) 0.5841(2) 0.8895(4) 0.0657(13) Uani 1 1 d . . .
H4 H 0.4867 0.5958 0.9537 0.079 Uiso 1 1 calc R . .
C5 C 0.3668(4) 0.6174(2) 0.8458(3) 0.0547(12) Uani 1 1 d . . .
H5 H 0.3349 0.6519 0.8801 0.066 Uiso 1 1 calc R . .
C6 C 0.3222(4) 0.6007(2) 0.7519(3) 0.0496(11) Uani 1 1 d . . .
C7 C 0.2228(4) 0.6332(2) 0.6999(3) 0.0481(11) Uani 1 1 d . . .
C8 C 0.0995(3) 0.72932(19) 0.7020(3) 0.0419(10) Uani 1 1 d . . .
C9 C -0.0004(4) 0.7008(2) 0.6653(3) 0.0461(10) Uani 1 1 d . . .
H9 H -0.0084 0.6545 0.6679 0.055 Uiso 1 1 calc R . .
C10 C -0.0871(4) 0.7383(2) 0.6255(3) 0.0513(11) Uani 1 1 d . . .
H10 H -0.1537 0.7180 0.5995 0.062 Uiso 1 1 calc R . .
C11 C -0.0766(4) 0.8063(2) 0.6237(3) 0.0508(11) Uani 1 1 d . . .
H11 H -0.1357 0.8327 0.5958 0.061 Uiso 1 1 calc R . .
C12 C 0.0199(4) 0.8351(2) 0.6627(3) 0.0472(10) Uani 1 1 d . . .
H12 H 0.0263 0.8816 0.6627 0.057 Uiso 1 1 calc R . .
C13 C 0.1080(3) 0.79747(18) 0.7019(3) 0.0388(9) Uani 1 1 d . . .
C14 C 0.2715(4) 0.82601(19) 0.8153(3) 0.0476(11) Uani 1 1 d . . .
C15 C 0.3598(3) 0.87696(18) 0.8306(3) 0.0430(10) Uani 1 1 d . . .
C16 C 0.4347(4) 0.8767(2) 0.9126(3) 0.0503(11) Uani 1 1 d . . .
H16 H 0.4324 0.8429 0.9599 0.060 Uiso 1 1 calc R . .
C17 C 0.5130(4) 0.9258(2) 0.9257(3) 0.0515(11) Uani 1 1 d . . .
H17 H 0.5651 0.9264 0.9818 0.062 Uiso 1 1 calc R . .
C18 C 0.5133(3) 0.9741(2) 0.8549(3) 0.0470(10) Uani 1 1 d . . .
H18 H 0.5650 1.0091 0.8620 0.056 Uiso 1 1 calc R . .
C19 C 0.4368(3) 0.97069(18) 0.7734(3) 0.0396(9) Uani 1 1 d . . .
C20 C 0.4380(3) 1.02061(19) 0.6929(3) 0.0410(9) Uani 1 1 d . . .
C21 C 0.3554(3) 1.04619(19) 0.5270(3) 0.0412(10) Uani 1 1 d . . .
C22 C 0.3703(3) 1.11427(19) 0.5291(3) 0.0491(11) Uani 1 1 d . . .
H22 H 0.3836 1.1363 0.5900 0.059 Uiso 1 1 calc R . .
C23 C 0.3658(4) 1.1495(2) 0.4430(3) 0.0559(12) Uani 1 1 d . . .
H23 H 0.3784 1.1955 0.4447 0.067 Uiso 1 1 calc R . .
C24 C 0.3430(4) 1.1179(2) 0.3543(3) 0.0576(12) Uani 1 1 d . . .
H24 H 0.3404 1.1422 0.2949 0.069 Uiso 1 1 calc R . .
C25 C 0.3240(4) 1.0514(2) 0.3520(3) 0.0518(11) Uani 1 1 d . . .
H25 H 0.3059 1.0302 0.2909 0.062 Uiso 1 1 calc R . .
C26 C 0.3307(3) 1.01493(18) 0.4375(3) 0.0428(10) Uani 1 1 d . . .
C27 C 0.2691(3) 0.9016(2) 0.4776(3) 0.0430(10) Uani 1 1 d . . .
C28 C 0.2807(3) 0.83143(19) 0.4489(3) 0.0397(9) Uani 1 1 d . . .
C29 C 0.3654(3) 0.8094(2) 0.3971(3) 0.0449(10) Uani 1 1 d . . .
H29 H 0.4176 0.8395 0.3758 0.054 Uiso 1 1 calc R . .
C30 C 0.3739(4) 0.7431(2) 0.3762(3) 0.0498(11) Uani 1 1 d . . .
H30 H 0.4324 0.7278 0.3411 0.060 Uiso 1 1 calc R . .
C31 C 0.2978(4) 0.69928(19) 0.4063(3) 0.0464(11) Uani 1 1 d . . .
C32 C 0.2122(4) 0.7211(2) 0.4566(3) 0.0507(11) Uani 1 1 d . . .
H32 H 0.1596 0.6909 0.4769 0.061 Uiso 1 1 calc R . .
C33 C 0.2029(4) 0.7871(2) 0.4776(3) 0.0479(11) Uani 1 1 d . . .
H33 H 0.1434 0.8022 0.5116 0.057 Uiso 1 1 calc R . .
C34 C 0.3126(5) 0.6317(3) 0.3879(4) 0.0724(15) Uani 1 1 d . . .
O100 O -0.2413(5) 0.5915(3) 0.6900(5) 0.152(2) Uani 1 1 d . . .
N100 N -0.3818(6) 0.6481(4) 0.6274(5) 0.112(2) Uani 1 1 d . . .
C100 C -0.3837(7) 0.6891(4) 0.7177(5) 0.120(3) Uani 1 1 d . . .
H10A H -0.3939 0.6608 0.7738 0.181 Uiso 1 1 calc R . .
H10B H -0.4445 0.7206 0.7088 0.181 Uiso 1 1 calc R . .
H10C H -0.3137 0.7129 0.7296 0.181 Uiso 1 1 calc R . .
C101 C -0.4728(7) 0.6677(4) 0.5520(6) 0.154(4) Uani 1 1 d . . .
H10D H -0.4434 0.6968 0.5039 0.231 Uiso 1 1 calc R . .
H10E H -0.5303 0.6908 0.5839 0.231 Uiso 1 1 calc R . .
H10F H -0.5043 0.6285 0.5189 0.231 Uiso 1 1 calc R . .
C102 C -0.3320(11) 0.5677(5) 0.5175(7) 0.226(7) Uani 1 1 d . . .
H10G H -0.3963 0.5866 0.4791 0.339 Uiso 1 1 calc R . .
H10H H -0.3443 0.5208 0.5276 0.339 Uiso 1 1 calc R . .
H10I H -0.2665 0.5737 0.4822 0.339 Uiso 1 1 calc R . .
C103 C -0.3146(10) 0.6025(5) 0.6176(10) 0.157(4) Uani 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
O1 C7 1.226(5) . ?
O2 C14 1.238(5) . ?
O3 C20 1.236(4) . ?
O4 C27 1.235(5) . ?
N1 C7 1.363(5) . ?
N1 C8 1.409(5) . ?
N1 H1N 0.80(4) . ?
N2 C14 1.347(5) . ?
N2 C13 1.421(5) . ?
N2 H2N 0.94(4) . ?
N3 C20 1.335(5) . ?
N3 C21 1.416(5) . ?
N3 H3N 0.87(4) . ?
N4 C27 1.341(5) . ?
N4 C26 1.431(5) . ?
N4 H4N 0.76(4) . ?
N5 C19 1.335(5) . ?
N5 C15 1.348(5) . ?
N6 C34 1.170(6) . ?
C1 C2 1.378(7) . ?
C1 C6 1.393(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.502(6) . ?
C8 C13 1.393(5) . ?
C8 C9 1.398(6) . ?
C9 C10 1.375(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(6) . ?
C12 H12 0.9500 . ?
C14 C15 1.496(6) . ?
C15 C16 1.379(6) . ?
C16 C17 1.383(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.503(5) . ?
C21 C26 1.391(5) . ?
C21 C22 1.400(5) . ?
C22 C23 1.379(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.376(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(5) . ?
C25 H25 0.9500 . ?
C27 C28 1.494(5) . ?
C28 C29 1.383(5) . ?
C28 C33 1.394(5) . ?
C29 C30 1.388(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.378(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.379(6) . ?
C31 C34 1.416(6) . ?
C32 C33 1.383(5) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
O100 C103 1.291(12) . ?
N100 C103 1.253(11) . ?
N100 C101 1.498(9) . ?
N100 C100 1.498(9) . ?
C100 H10A 0.9800 . ?
C100 H10B 0.9800 . ?
C100 H10C 0.9800 . ?
C101 H10D 0.9800 . ?
C101 H10E 0.9800 . ?
C101 H10F 0.9800 . ?
C102 C103 1.542(14) . ?
C102 H10G 0.9800 . ?
C102 H10H 0.9800 . ?
C102 H10I 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
C7 N1 C8 126.1(4) . . ?
C7 N1 H1N 118(3) . . ?
C8 N1 H1N 116(3) . . ?
C14 N2 C13 127.1(3) . . ?
C14 N2 H2N 119(2) . . ?
C13 N2 H2N 112(3) . . ?
C20 N3 C21 126.5(3) . . ?
C20 N3 H3N 120(3) . . ?
C21 N3 H3N 113(3) . . ?
C27 N4 C26 129.5(4) . . ?
C27 N4 H4N 122(4) . . ?
C26 N4 H4N 108(4) . . ?
C19 N5 C15 118.0(3) . . ?
C2 C1 C6 120.5(5) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 120.5(5) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.6(5) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 118.6(4) . . ?
C5 C6 C7 124.0(4) . . ?
C1 C6 C7 117.4(4) . . ?
O1 C7 N1 122.3(4) . . ?
O1 C7 C6 121.2(4) . . ?
N1 C7 C6 116.6(4) . . ?
C13 C8 C9 118.5(4) . . ?
C13 C8 N1 120.0(4) . . ?
C9 C8 N1 121.5(4) . . ?
C10 C9 C8 121.4(4) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 121.0(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C8 119.9(4) . . ?
C12 C13 N2 116.0(3) . . ?
C8 C13 N2 123.8(4) . . ?
O2 C14 N2 124.9(4) . . ?
O2 C14 C15 120.9(4) . . ?
N2 C14 C15 114.2(3) . . ?
N5 C15 C16 122.1(4) . . ?
N5 C15 C14 116.4(3) . . ?
C16 C15 C14 121.6(4) . . ?
C15 C16 C17 119.9(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 118.1(4) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C17 C18 C19 118.9(4) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
N5 C19 C18 123.0(4) . . ?
N5 C19 C20 116.6(3) . . ?
C18 C19 C20 120.4(4) . . ?
O3 C20 N3 125.6(4) . . ?
O3 C20 C19 119.3(4) . . ?
N3 C20 C19 115.0(3) . . ?
C26 C21 C22 119.3(4) . . ?
C26 C21 N3 120.3(3) . . ?
C22 C21 N3 120.4(4) . . ?
C23 C22 C21 120.3(4) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 119.9(4) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.9(4) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C21 119.5(4) . . ?
C25 C26 N4 116.7(4) . . ?
C21 C26 N4 123.4(4) . . ?
O4 C27 N4 122.8(4) . . ?
O4 C27 C28 121.4(4) . . ?
N4 C27 C28 115.8(4) . . ?
C29 C28 C33 119.7(4) . . ?
C29 C28 C27 122.7(4) . . ?
C33 C28 C27 117.5(4) . . ?
C28 C29 C30 119.7(4) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 120.3(4) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 120.2(4) . . ?
C30 C31 C34 118.5(4) . . ?
C32 C31 C34 121.3(4) . . ?
C31 C32 C33 120.0(4) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 C28 120.0(4) . . ?
C32 C33 H33 120.0 . . ?
C28 C33 H33 120.0 . . ?
N6 C34 C31 179.1(6) . . ?
C103 N100 C101 124.9(10) . . ?
C103 N100 C100 124.4(9) . . ?
C101 N100 C100 110.7(8) . . ?
N100 C100 H10A 109.5 . . ?
N100 C100 H10B 109.5 . . ?
H10A C100 H10B 109.5 . . ?
N100 C100 H10C 109.5 . . ?
H10A C100 H10C 109.5 . . ?
H10B C100 H10C 109.5 . . ?
N100 C101 H10D 109.5 . . ?
N100 C101 H10E 109.5 . . ?
H10D C101 H10E 109.5 . . ?
N100 C101 H10F 109.5 . . ?
H10D C101 H10F 109.5 . . ?
H10E C101 H10F 109.5 . . ?
C103 C102 H10G 109.5 . . ?
C103 C102 H10H 109.5 . . ?
H10G C102 H10H 109.5 . . ?
C103 C102 H10I 109.5 . . ?
H10G C102 H10I 109.5 . . ?
H10H C102 H10I 109.5 . . ?
N100 C103 O100 117.2(13) . . ?
N100 C103 C102 113.6(12) . . ?
O100 C103 C102 129.2(12) . . ?

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
C6 C1 C2 C3 1.8(8) . . . . ?
C1 C2 C3 C4 -1.8(8) . . . . ?
C2 C3 C4 C5 0.8(8) . . . . ?
C3 C4 C5 C6 0.2(7) . . . . ?
C4 C5 C6 C1 -0.3(7) . . . . ?
C4 C5 C6 C7 178.6(4) . . . . ?
C2 C1 C6 C5 -0.7(7) . . . . ?
C2 C1 C6 C7 -179.7(4) . . . . ?
C8 N1 C7 O1 0.1(6) . . . . ?
C8 N1 C7 C6 -179.8(4) . . . . ?
C5 C6 C7 O1 -165.5(4) . . . . ?
C1 C6 C7 O1 13.4(6) . . . . ?
C5 C6 C7 N1 14.5(6) . . . . ?
C1 C6 C7 N1 -166.6(4) . . . . ?
C7 N1 C8 C13 -140.4(4) . . . . ?
C7 N1 C8 C9 39.6(6) . . . . ?
C13 C8 C9 C10 3.0(6) . . . . ?
N1 C8 C9 C10 -177.0(4) . . . . ?
C8 C9 C10 C11 -1.5(6) . . . . ?
C9 C10 C11 C12 -0.7(6) . . . . ?
C10 C11 C12 C13 1.4(6) . . . . ?
C11 C12 C13 C8 0.1(6) . . . . ?
C11 C12 C13 N2 173.6(4) . . . . ?
C9 C8 C13 C12 -2.3(6) . . . . ?
N1 C8 C13 C12 177.7(4) . . . . ?
C9 C8 C13 N2 -175.2(3) . . . . ?
N1 C8 C13 N2 4.8(6) . . . . ?
C14 N2 C13 C12 133.0(4) . . . . ?
C14 N2 C13 C8 -53.8(6) . . . . ?
C13 N2 C14 O2 8.6(7) . . . . ?
C13 N2 C14 C15 -170.3(4) . . . . ?
C19 N5 C15 C16 -1.0(6) . . . . ?
C19 N5 C15 C14 178.1(3) . . . . ?
O2 C14 C15 N5 -176.4(4) . . . . ?
N2 C14 C15 N5 2.6(5) . . . . ?
O2 C14 C15 C16 2.7(6) . . . . ?
N2 C14 C15 C16 -178.3(4) . . . . ?
N5 C15 C16 C17 1.1(6) . . . . ?
C14 C15 C16 C17 -178.0(4) . . . . ?
C15 C16 C17 C18 0.0(6) . . . . ?
C16 C17 C18 C19 -1.1(6) . . . . ?
C15 N5 C19 C18 -0.2(6) . . . . ?
C15 N5 C19 C20 178.3(3) . . . . ?
C17 C18 C19 N5 1.3(6) . . . . ?
C17 C18 C19 C20 -177.2(4) . . . . ?
C21 N3 C20 O3 2.0(6) . . . . ?
C21 N3 C20 C19 -175.7(3) . . . . ?
N5 C19 C20 O3 178.7(3) . . . . ?
C18 C19 C20 O3 -2.7(6) . . . . ?
N5 C19 C20 N3 -3.5(5) . . . . ?
C18 C19 C20 N3 175.1(4) . . . . ?
C20 N3 C21 C26 143.1(4) . . . . ?
C20 N3 C21 C22 -36.3(6) . . . . ?
C26 C21 C22 C23 -3.1(6) . . . . ?
N3 C21 C22 C23 176.3(4) . . . . ?
C21 C22 C23 C24 2.1(7) . . . . ?
C22 C23 C24 C25 0.5(7) . . . . ?
C23 C24 C25 C26 -2.0(7) . . . . ?
C24 C25 C26 C21 1.0(7) . . . . ?
C24 C25 C26 N4 -172.4(4) . . . . ?
C22 C21 C26 C25 1.5(6) . . . . ?
N3 C21 C26 C25 -177.9(4) . . . . ?
C22 C21 C26 N4 174.4(4) . . . . ?
N3 C21 C26 N4 -5.0(6) . . . . ?
C27 N4 C26 C25 -138.5(4) . . . . ?
C27 N4 C26 C21 48.3(7) . . . . ?
C26 N4 C27 O4 -0.6(7) . . . . ?
C26 N4 C27 C28 -178.7(4) . . . . ?
O4 C27 C28 C29 -158.8(4) . . . . ?
N4 C27 C28 C29 19.4(6) . . . . ?
O4 C27 C28 C33 20.3(6) . . . . ?
N4 C27 C28 C33 -161.6(4) . . . . ?
C33 C28 C29 C30 -1.6(6) . . . . ?
C27 C28 C29 C30 177.4(4) . . . . ?
C28 C29 C30 C31 0.5(6) . . . . ?
C29 C30 C31 C32 0.5(6) . . . . ?
C29 C30 C31 C34 -176.9(4) . . . . ?
C30 C31 C32 C33 -0.4(6) . . . . ?
C34 C31 C32 C33 176.9(4) . . . . ?
C31 C32 C33 C28 -0.7(6) . . . . ?
C29 C28 C33 C32 1.8(6) . . . . ?
C27 C28 C33 C32 -177.3(4) . . . . ?
C101 N100 C103 O100 -179.5(6) . . . . ?
C100 N100 C103 O100 -1.2(13) . . . . ?
C101 N100 C103 C102 1.0(12) . . . . ?
C100 N100 C103 C102 179.3(6) . . . . ?

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 O2 0.80(4) 2.05(4) 2.765(4) 149(4) .
N2 H2N O4 0.94(4) 2.24(4) 3.085(4) 150(3) .
N3 H3N O4 0.87(4) 1.95(4) 2.736(4) 151(4) .
N4 H4N O3 0.76(4) 2.21(5) 2.869(5) 146(5) 3_676
N2 H2N N5 0.94(4) 2.23(4) 2.648(5) 106(3) .
N3 H3N N5 0.87(4) 2.29(4) 2.667(4) 106(3) .

_diffrn_measured_fraction_theta_max 0.900
_diffrn_reflns_theta_full        66.77
_diffrn_measured_fraction_theta_full 0.900
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_7-THF-S1
_database_code_depnum_ccdc_archive 'CCDC 1436670'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H24 N6 O4, C4 H8 O'
_chemical_formula_sum            'C38 H32 N6 O5'
_chemical_formula_weight         652.70

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   12.2684(4)
_cell_length_b                   20.2242(7)
_cell_length_c                   13.8112(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.246(2)
_cell_angle_gamma                90.00
_cell_volume                     3391.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1368
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8600
_exptl_absorpt_correction_T_max  0.9199
_exptl_absorpt_process_details   
;
Denzo (otwinowski, Borek, Majewski & Minor, 2003) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KappaCCD, Cu, APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10320
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_sigmaI/netI    0.0700
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.90
_diffrn_reflns_theta_max         67.00
_reflns_number_total             5819
_reflns_number_gt                3786
_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)+(0.1058P)²+4.3995P] 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         5819
_refine_ls_number_parameters     429
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0830
_refine_ls_wR_factor_ref         0.2409
_refine_ls_wR_factor_gt          0.2100
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3294(3) 0.60711(16) 0.8641(2) 0.0568(8) Uani 1 1 d . . .
O2 O 0.2209(3) 0.78435(15) 0.6188(2) 0.0559(8) Uani 1 1 d . . .
O3 O -0.0174(2) 1.06743(13) 0.79513(18) 0.0411(7) Uani 1 1 d . . .
O4 O 0.2775(2) 0.91736(14) 0.95486(19) 0.0443(7) Uani 1 1 d . . .
N1 N 0.3031(3) 0.69178(17) 0.7553(2) 0.0433(8) Uani 1 1 d D . .
H1N H 0.256(3) 0.710(2) 0.709(2) 0.052 Uiso 1 1 d D . .
N2 N 0.2818(3) 0.83354(17) 0.7652(2) 0.0418(8) Uani 1 1 d D . .
H2N H 0.267(3) 0.8678(16) 0.803(3) 0.050 Uiso 1 1 d D . .
N3 N 0.1283(3) 1.01205(17) 0.8792(2) 0.0397(8) Uani 1 1 d D . .
H3N H 0.171(3) 0.9765(15) 0.880(3) 0.048 Uiso 1 1 d D . .
N4 N 0.1665(3) 0.94538(17) 1.0669(2) 0.0406(8) Uani 1 1 d D . .
H4N H 0.135(3) 0.931(2) 1.118(2) 0.049 Uiso 1 1 d D . .
N5 N 0.1270(3) 0.92549(16) 0.7339(2) 0.0385(8) Uani 1 1 d . . .
N6 N 0.1757(5) 0.5712(3) 1.1201(4) 0.0899(16) Uani 1 1 d . . .
C1 C 0.1224(4) 0.6169(2) 0.6481(3) 0.0517(11) Uani 1 1 d . . .
H1 H 0.1502 0.6526 0.6143 0.062 Uiso 1 1 calc R . .
C2 C 0.0300(4) 0.5827(3) 0.6056(4) 0.0616(13) Uani 1 1 d . . .
H2 H -0.0044 0.5945 0.5419 0.074 Uiso 1 1 calc R . .
C3 C -0.0125(4) 0.5315(3) 0.6545(4) 0.0685(14) Uani 1 1 d . . .
H3 H -0.0757 0.5081 0.6249 0.082 Uiso 1 1 calc R . .
C4 C 0.0380(4) 0.5148(2) 0.7474(4) 0.0673(14) Uani 1 1 d . . .
H4 H 0.0080 0.4804 0.7822 0.081 Uiso 1 1 calc R . .
C5 C 0.1315(4) 0.5477(2) 0.7902(4) 0.0584(12) Uani 1 1 d . . .
H5 H 0.1662 0.5352 0.8535 0.070 Uiso 1 1 calc R . .
C6 C 0.1743(3) 0.5988(2) 0.7406(3) 0.0445(10) Uani 1 1 d . . .
C7 C 0.2757(4) 0.6325(2) 0.7926(3) 0.0446(10) Uani 1 1 d . . .
C8 C 0.3936(3) 0.7311(2) 0.7938(3) 0.0410(9) Uani 1 1 d . . .
C9 C 0.4950(3) 0.7037(2) 0.8316(3) 0.0451(10) Uani 1 1 d . . .
H9 H 0.5047 0.6571 0.8284 0.054 Uiso 1 1 calc R . .
C10 C 0.5811(4) 0.7421(2) 0.8732(3) 0.0507(11) Uani 1 1 d . . .
H10 H 0.6490 0.7221 0.8994 0.061 Uiso 1 1 calc R . .
C11 C 0.5692(4) 0.8106(2) 0.8773(3) 0.0521(11) Uani 1 1 d . . .
H11 H 0.6283 0.8374 0.9070 0.063 Uiso 1 1 calc R . .
C12 C 0.4705(4) 0.8388(2) 0.8376(3) 0.0482(10) Uani 1 1 d . . .
H12 H 0.4625 0.8856 0.8389 0.058 Uiso 1 1 calc R . .
C13 C 0.3822(3) 0.8001(2) 0.7956(3) 0.0402(9) Uani 1 1 d . . .
C14 C 0.2142(4) 0.8274(2) 0.6802(3) 0.0443(10) Uani 1 1 d . . .
C15 C 0.1260(3) 0.87980(19) 0.6641(3) 0.0394(9) Uani 1 1 d . . .
C16 C 0.0498(4) 0.8798(2) 0.5799(3) 0.0469(10) Uani 1 1 d . . .
H16 H 0.0513 0.8464 0.5318 0.056 Uiso 1 1 calc R . .
C17 C -0.0281(4) 0.9290(2) 0.5672(3) 0.0469(10) Uani 1 1 d . . .
H17 H -0.0815 0.9300 0.5101 0.056 Uiso 1 1 calc R . .
C18 C -0.0279(3) 0.9770(2) 0.6383(3) 0.0427(10) Uani 1 1 d . . .
H18 H -0.0802 1.0119 0.6308 0.051 Uiso 1 1 calc R . .
C19 C 0.0506(3) 0.97308(18) 0.7210(3) 0.0355(9) Uani 1 1 d . . .
C20 C 0.0515(3) 1.02252(19) 0.8019(3) 0.0360(9) Uani 1 1 d . . .
C21 C 0.1421(3) 1.04832(19) 0.9677(3) 0.0371(9) Uani 1 1 d . . .
C22 C 0.1331(3) 1.1172(2) 0.9665(3) 0.0419(9) Uani 1 1 d . . .
H22 H 0.1211 1.1399 0.9057 0.050 Uiso 1 1 calc R . .
C23 C 0.1413(4) 1.1526(2) 1.0524(3) 0.0486(11) Uani 1 1 d . . .
H23 H 0.1328 1.1992 1.0508 0.058 Uiso 1 1 calc R . .
C24 C 0.1618(4) 1.1200(2) 1.1408(3) 0.0502(11) Uani 1 1 d . . .
H24 H 0.1675 1.1443 1.2002 0.060 Uiso 1 1 calc R . .
C25 C 0.1743(3) 1.0522(2) 1.1434(3) 0.0433(10) Uani 1 1 d . . .
H25 H 0.1898 1.0301 1.2046 0.052 Uiso 1 1 calc R . .
C26 C 0.1644(3) 1.01577(19) 1.0570(3) 0.0371(9) Uani 1 1 d . . .
C27 C 0.2215(3) 0.9012(2) 1.0187(3) 0.0383(9) Uani 1 1 d . . .
C28 C 0.2110(3) 0.8296(2) 1.0465(3) 0.0399(9) Uani 1 1 d . . .
C29 C 0.2839(4) 0.7852(2) 1.0153(3) 0.0513(11) Uani 1 1 d . . .
H29 H 0.3402 0.8007 0.9805 0.062 Uiso 1 1 calc R . .
C30 C 0.2758(4) 0.7183(2) 1.0343(3) 0.0565(12) Uani 1 1 d . . .
H30 H 0.3259 0.6879 1.0122 0.068 Uiso 1 1 calc R . .
C31 C 0.1940(4) 0.6960(2) 1.0859(3) 0.0487(11) Uani 1 1 d . . .
C32 C 0.1223(4) 0.7397(2) 1.1188(3) 0.0544(11) Uani 1 1 d . . .
H32 H 0.0671 0.7240 1.1548 0.065 Uiso 1 1 calc R . .
C33 C 0.1300(4) 0.8066(2) 1.0995(3) 0.0487(11) Uani 1 1 d . . .
H33 H 0.0802 0.8368 1.1224 0.058 Uiso 1 1 calc R . .
C34 C 0.1830(5) 0.6267(3) 1.1044(4) 0.0655(14) Uani 1 1 d . . .
O100 O 0.0743(10) 0.3308(6) 1.0699(9) 0.250(5) Uiso 1 1 d . . .
C100 C 0.1305(9) 0.3336(5) 1.1799(7) 0.147(3) Uiso 1 1 d . . .
H10A H 0.0771 0.3442 1.2250 0.177 Uiso 1 1 calc R . .
H10B H 0.1696 0.2920 1.2008 0.177 Uiso 1 1 calc R . .
C101 C 0.2087(6) 0.3895(4) 1.1710(6) 0.107(2) Uiso 1 1 d . . .
H11A H 0.1819 0.4294 1.2019 0.128 Uiso 1 1 calc R . .
H11B H 0.2817 0.3780 1.2074 0.128 Uiso 1 1 calc R . .
C102 C 0.2209(11) 0.4047(6) 1.0730(9) 0.181(5) Uiso 1 1 d . . .
H12A H 0.2350 0.4523 1.0640 0.218 Uiso 1 1 calc R . .
H12B H 0.2799 0.3782 1.0498 0.218 Uiso 1 1 calc R . .
C103 C 0.1149(14) 0.3856(8) 1.0270(11) 0.225(6) Uiso 1 1 d . . .
H13A H 0.0633 0.4230 1.0298 0.270 Uiso 1 1 calc R . .
H13B H 0.1183 0.3759 0.9573 0.270 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
O1 C7 1.219(5) . ?
O2 C14 1.227(5) . ?
O3 C20 1.235(4) . ?
O4 C27 1.238(5) . ?
N1 C7 1.366(5) . ?
N1 C8 1.407(5) . ?
N1 H1N 0.880(19) . ?
N2 C14 1.342(5) . ?
N2 C13 1.415(5) . ?
N2 H2N 0.901(19) . ?
N3 C20 1.337(5) . ?
N3 C21 1.414(5) . ?
N3 H3N 0.892(19) . ?
N4 C27 1.351(5) . ?
N4 C26 1.430(5) . ?
N4 H4N 0.901(19) . ?
N5 C15 1.334(5) . ?
N5 C19 1.338(5) . ?
N6 C34 1.148(6) . ?
C1 C2 1.385(6) . ?
C1 C6 1.393(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.378(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.507(6) . ?
C8 C9 1.393(6) . ?
C8 C13 1.402(6) . ?
C9 C10 1.370(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(6) . ?
C12 H12 0.9500 . ?
C14 C15 1.507(6) . ?
C15 C16 1.384(6) . ?
C16 C17 1.372(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.498(5) . ?
C21 C26 1.390(5) . ?
C21 C22 1.398(5) . ?
C22 C23 1.376(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.393(5) . ?
C25 H25 0.9500 . ?
C27 C28 1.508(6) . ?
C28 C29 1.379(6) . ?
C28 C33 1.395(6) . ?
C29 C30 1.384(6) . ?
C29 H29 0.9500 . ?
C30 C31 1.387(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.370(6) . ?
C31 C34 1.435(7) . ?
C32 C33 1.385(6) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
O100 C103 1.383(16) . ?
O100 C100 1.578(13) . ?
C100 C101 1.499(11) . ?
C100 H10A 0.9900 . ?
C100 H10B 0.9900 . ?
C101 C102 1.417(12) . ?
C101 H11A 0.9900 . ?
C101 H11B 0.9900 . ?
C102 C103 1.416(16) . ?
C102 H12A 0.9900 . ?
C102 H12B 0.9900 . ?
C103 H13A 0.9900 . ?
C103 H13B 0.9900 . ?

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
C7 N1 C8 125.2(3) . . ?
C7 N1 H1N 118(3) . . ?
C8 N1 H1N 116(3) . . ?
C14 N2 C13 128.2(3) . . ?
C14 N2 H2N 115(3) . . ?
C13 N2 H2N 116(3) . . ?
C20 N3 C21 126.3(3) . . ?
C20 N3 H3N 119(3) . . ?
C21 N3 H3N 114(3) . . ?
C27 N4 C26 128.0(3) . . ?
C27 N4 H4N 118(3) . . ?
C26 N4 H4N 113(3) . . ?
C15 N5 C19 118.0(3) . . ?
C2 C1 C6 119.8(4) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C2 C1 120.7(5) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.2(5) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.9(5) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 C7 116.6(4) . . ?
C1 C6 C7 123.8(4) . . ?
O1 C7 N1 122.8(4) . . ?
O1 C7 C6 120.5(4) . . ?
N1 C7 C6 116.6(4) . . ?
C9 C8 C13 118.5(4) . . ?
C9 C8 N1 122.0(4) . . ?
C13 C8 N1 119.5(4) . . ?
C10 C9 C8 121.6(4) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 121.2(4) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 119.5(4) . . ?
C12 C13 N2 116.4(4) . . ?
C8 C13 N2 123.8(4) . . ?
O2 C14 N2 125.1(4) . . ?
O2 C14 C15 121.0(4) . . ?
N2 C14 C15 113.9(3) . . ?
N5 C15 C16 122.8(4) . . ?
N5 C15 C14 116.6(3) . . ?
C16 C15 C14 120.5(4) . . ?
C17 C16 C15 118.8(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 119.2(4) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C19 118.4(4) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
N5 C19 C18 122.8(4) . . ?
N5 C19 C20 116.8(3) . . ?
C18 C19 C20 120.4(4) . . ?
O3 C20 N3 125.0(4) . . ?
O3 C20 C19 120.2(3) . . ?
N3 C20 C19 114.8(3) . . ?
C26 C21 C22 119.2(4) . . ?
C26 C21 N3 120.3(4) . . ?
C22 C21 N3 120.5(4) . . ?
C23 C22 C21 120.8(4) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 119.8(4) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 120.3(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 120.5(4) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 119.5(4) . . ?
C21 C26 N4 123.6(3) . . ?
C25 C26 N4 116.5(3) . . ?
O4 C27 N4 122.9(4) . . ?
O4 C27 C28 120.8(3) . . ?
N4 C27 C28 116.3(3) . . ?
C29 C28 C33 119.3(4) . . ?
C29 C28 C27 117.5(4) . . ?
C33 C28 C27 123.1(4) . . ?
C28 C29 C30 120.7(4) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C29 C30 C31 119.4(4) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C32 C31 C30 120.5(4) . . ?
C32 C31 C34 119.3(5) . . ?
C30 C31 C34 120.2(4) . . ?
C31 C32 C33 120.1(4) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C28 120.0(4) . . ?
C32 C33 H33 120.0 . . ?
C28 C33 H33 120.0 . . ?
N6 C34 C31 179.0(6) . . ?
C103 O100 C100 104.4(11) . . ?
C101 C100 O100 98.3(8) . . ?
C101 C100 H10A 112.1 . . ?
O100 C100 H10A 112.1 . . ?
C101 C100 H10B 112.1 . . ?
O100 C100 H10B 112.1 . . ?
H10A C100 H10B 109.7 . . ?
C102 C101 C100 113.5(8) . . ?
C102 C101 H11A 108.9 . . ?
C100 C101 H11A 108.9 . . ?
C102 C101 H11B 108.9 . . ?
C100 C101 H11B 108.9 . . ?
H11A C101 H11B 107.7 . . ?
C103 C102 C101 98.8(11) . . ?
C103 C102 H12A 112.0 . . ?
C101 C102 H12A 112.0 . . ?
C103 C102 H12B 112.0 . . ?
C101 C102 H12B 112.0 . . ?
H12A C102 H12B 109.7 . . ?
O100 C103 C102 113.0(14) . . ?
O100 C103 H13A 109.0 . . ?
C102 C103 H13A 109.0 . . ?
O100 C103 H13B 109.0 . . ?
C102 C103 H13B 109.0 . . ?
H13A C103 H13B 107.8 . . ?

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
C6 C1 C2 C3 1.2(7) . . . . ?
C1 C2 C3 C4 0.3(8) . . . . ?
C2 C3 C4 C5 -1.5(8) . . . . ?
C3 C4 C5 C6 1.2(8) . . . . ?
C4 C5 C6 C1 0.3(7) . . . . ?
C4 C5 C6 C7 179.4(4) . . . . ?
C2 C1 C6 C5 -1.5(7) . . . . ?
C2 C1 C6 C7 179.4(4) . . . . ?
C8 N1 C7 O1 -1.0(6) . . . . ?
C8 N1 C7 C6 179.2(4) . . . . ?
C5 C6 C7 O1 15.0(6) . . . . ?
C1 C6 C7 O1 -165.9(4) . . . . ?
C5 C6 C7 N1 -165.2(4) . . . . ?
C1 C6 C7 N1 13.9(6) . . . . ?
C7 N1 C8 C9 38.6(6) . . . . ?
C7 N1 C8 C13 -140.8(4) . . . . ?
C13 C8 C9 C10 2.6(6) . . . . ?
N1 C8 C9 C10 -176.8(4) . . . . ?
C8 C9 C10 C11 -1.0(7) . . . . ?
C9 C10 C11 C12 -1.0(7) . . . . ?
C10 C11 C12 C13 1.4(7) . . . . ?
C11 C12 C13 C8 0.2(6) . . . . ?
C11 C12 C13 N2 174.4(4) . . . . ?
C9 C8 C13 C12 -2.1(6) . . . . ?
N1 C8 C13 C12 177.3(4) . . . . ?
C9 C8 C13 N2 -175.9(4) . . . . ?
N1 C8 C13 N2 3.5(6) . . . . ?
C14 N2 C13 C12 133.7(4) . . . . ?
C14 N2 C13 C8 -52.4(6) . . . . ?
C13 N2 C14 O2 10.7(7) . . . . ?
C13 N2 C14 C15 -168.8(4) . . . . ?
C19 N5 C15 C16 0.0(6) . . . . ?
C19 N5 C15 C14 179.2(3) . . . . ?
O2 C14 C15 N5 -178.4(4) . . . . ?
N2 C14 C15 N5 1.1(5) . . . . ?
O2 C14 C15 C16 0.8(6) . . . . ?
N2 C14 C15 C16 -179.7(4) . . . . ?
N5 C15 C16 C17 0.2(7) . . . . ?
C14 C15 C16 C17 -178.9(4) . . . . ?
C15 C16 C17 C18 0.2(7) . . . . ?
C16 C17 C18 C19 -0.9(6) . . . . ?
C15 N5 C19 C18 -0.7(6) . . . . ?
C15 N5 C19 C20 178.2(3) . . . . ?
C17 C18 C19 N5 1.2(6) . . . . ?
C17 C18 C19 C20 -177.7(4) . . . . ?
C21 N3 C20 O3 2.5(6) . . . . ?
C21 N3 C20 C19 -175.4(4) . . . . ?
N5 C19 C20 O3 -179.4(3) . . . . ?
C18 C19 C20 O3 -0.5(6) . . . . ?
N5 C19 C20 N3 -1.4(5) . . . . ?
C18 C19 C20 N3 177.5(4) . . . . ?
C20 N3 C21 C26 137.4(4) . . . . ?
C20 N3 C21 C22 -42.3(6) . . . . ?
C26 C21 C22 C23 -2.8(6) . . . . ?
N3 C21 C22 C23 176.9(4) . . . . ?
C21 C22 C23 C24 1.9(6) . . . . ?
C22 C23 C24 C25 0.1(7) . . . . ?
C23 C24 C25 C26 -1.1(7) . . . . ?
C22 C21 C26 C25 1.8(6) . . . . ?
N3 C21 C26 C25 -178.0(4) . . . . ?
C22 C21 C26 N4 174.7(4) . . . . ?
N3 C21 C26 N4 -5.0(6) . . . . ?
C24 C25 C26 C21 0.2(6) . . . . ?
C24 C25 C26 N4 -173.3(4) . . . . ?
C27 N4 C26 C21 50.7(6) . . . . ?
C27 N4 C26 C25 -136.1(4) . . . . ?
C26 N4 C27 O4 -2.1(6) . . . . ?
C26 N4 C27 C28 178.2(3) . . . . ?
O4 C27 C28 C29 14.1(6) . . . . ?
N4 C27 C28 C29 -166.1(4) . . . . ?
O4 C27 C28 C33 -164.2(4) . . . . ?
N4 C27 C28 C33 15.6(5) . . . . ?
C33 C28 C29 C30 1.4(6) . . . . ?
C27 C28 C29 C30 -177.0(4) . . . . ?
C28 C29 C30 C31 -0.5(7) . . . . ?
C29 C30 C31 C32 -0.7(7) . . . . ?
C29 C30 C31 C34 178.7(4) . . . . ?
C30 C31 C32 C33 0.9(7) . . . . ?
C34 C31 C32 C33 -178.5(4) . . . . ?
C31 C32 C33 C28 0.0(7) . . . . ?
C29 C28 C33 C32 -1.1(6) . . . . ?
C27 C28 C33 C32 177.1(4) . . . . ?
C103 O100 C100 C101 -7.7(13) . . . . ?
O100 C100 C101 C102 -14.5(11) . . . . ?
C100 C101 C102 C103 29.9(13) . . . . ?
C100 O100 C103 C102 28.3(17) . . . . ?
C101 C102 C103 O100 -36.1(16) . . . . ?

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 O2 0.880(19) 1.96(3) 2.744(4) 148(4) .
N2 H2N N5 0.901(19) 2.18(4) 2.649(4) 112(3) .
N2 H2N O4 0.901(19) 2.31(3) 3.127(4) 150(4) .
N3 H3N O4 0.892(19) 1.95(3) 2.750(4) 148(4) .
N3 H3N N5 0.892(19) 2.27(4) 2.662(4) 107(3) .
N4 H4N O3 0.901(19) 2.00(3) 2.837(4) 153(4) 3_577

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.065

# start Validation Reply Form
_vrf_DIFMX01_ais026              
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: This is residual electron density near a disordered solvent molecule. A disorder model could not be found
and the molecule was left isotropic and disorder unrefined.
;
_vrf_PLAT097_ais026              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.84 eA-3 
RESPONSE: This is residual electron density near a disordered solvent molecule. A disorder model could not be found
and the molecule was left isotropic and disorder unrefined
;
####################################################################### 
# 
# 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_4-Diox-S1
_database_code_depnum_ccdc_archive 'CCDC 1436671'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H23 N5 O4, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C30 H27 N5 O5'
_chemical_formula_weight         537.57

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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7193(2)
_cell_length_b                   13.1332(3)
_cell_length_c                   13.2791(5)
_cell_angle_alpha                114.6880(10)
_cell_angle_beta                 97.2880(10)
_cell_angle_gamma                103.6930(10)
_cell_volume                     1297.73(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9792
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_process_details   
;
Denzo (otwinowski, Borek, Majewski & Minor, 2003) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'KappaCCD, Mo, APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13017
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         28.66
_reflns_number_total             6647
_reflns_number_gt                4386
_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)+(0.0536P)²+0.5853P] 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         6647
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2732(2) -0.17081(14) 0.08721(13) 0.0403(4) Uani 1 1 d . . .
O2 O 0.20393(17) 0.14641(12) 0.41482(12) 0.0292(3) Uani 1 1 d . . .
O3 O 0.53121(19) 0.64096(12) 0.33171(13) 0.0344(4) Uani 1 1 d . . .
O4 O 0.73941(17) 0.31430(11) 0.31683(12) 0.0265(3) Uani 1 1 d . . .
N1 N 0.2498(2) -0.05036(14) 0.26156(14) 0.0264(4) Uani 1 1 d . . .
H1N H 0.196(3) -0.009(2) 0.297(2) 0.032 Uiso 1 1 d . . .
N2 N 0.4537(2) 0.19178(14) 0.37634(14) 0.0246(3) Uani 1 1 d . . .
H2N H 0.525(3) 0.243(2) 0.369(2) 0.030 Uiso 1 1 d . . .
N3 N 0.6503(2) 0.49744(14) 0.31179(14) 0.0246(4) Uani 1 1 d . . .
H3N H 0.638(3) 0.440(2) 0.321(2) 0.029 Uiso 1 1 d . . .
N4 N 0.7603(2) 0.32172(14) 0.15082(15) 0.0249(4) Uani 1 1 d . . .
H4N H 0.749(3) 0.276(2) 0.076(2) 0.030 Uiso 1 1 d . . .
N5 N 0.41221(19) 0.38281(13) 0.36787(13) 0.0219(3) Uani 1 1 d . . .
C1 C -0.0954(3) -0.11705(19) 0.1645(2) 0.0347(5) Uani 1 1 d . . .
H1 H -0.0637 -0.0947 0.2438 0.042 Uiso 1 1 calc R . .
C2 C -0.2536(3) -0.1327(2) 0.1146(2) 0.0440(6) Uani 1 1 d . . .
H2 H -0.3303 -0.1211 0.1597 0.053 Uiso 1 1 calc R . .
C3 C -0.3003(3) -0.1650(2) -0.0001(2) 0.0509(7) Uani 1 1 d . . .
H3 H -0.4097 -0.1771 -0.0346 0.061 Uiso 1 1 calc R . .
C4 C -0.1889(4) -0.1799(3) -0.0648(2) 0.0569(8) Uani 1 1 d . . .
H4 H -0.2208 -0.2003 -0.1437 0.068 Uiso 1 1 calc R . .
C5 C -0.0306(3) -0.1653(2) -0.0158(2) 0.0465(6) Uani 1 1 d . . .
H5 H 0.0454 -0.1769 -0.0615 0.056 Uiso 1 1 calc R . .
C6 C 0.0181(3) -0.13379(17) 0.09935(18) 0.0296(4) Uani 1 1 d . . .
C7 C 0.1903(3) -0.12092(17) 0.14761(17) 0.0279(4) Uani 1 1 d . . .
C8 C 0.4128(2) -0.01896(16) 0.32291(16) 0.0240(4) Uani 1 1 d . . .
C9 C 0.4772(3) -0.10465(17) 0.32864(18) 0.0300(4) Uani 1 1 d . . .
H9 H 0.4097 -0.1850 0.2934 0.036 Uiso 1 1 calc R . .
C10 C 0.6383(3) -0.07351(19) 0.38521(19) 0.0340(5) Uani 1 1 d . . .
H10 H 0.6813 -0.1325 0.3884 0.041 Uiso 1 1 calc R . .
C11 C 0.7375(3) 0.04371(19) 0.43738(18) 0.0334(5) Uani 1 1 d . . .
H11 H 0.8491 0.0648 0.4745 0.040 Uiso 1 1 calc R . .
C12 C 0.6734(3) 0.12968(18) 0.43508(17) 0.0297(4) Uani 1 1 d . . .
H12 H 0.7411 0.2101 0.4719 0.036 Uiso 1 1 calc R . .
C13 C 0.5112(2) 0.09991(16) 0.37965(16) 0.0233(4) Uani 1 1 d . . .
C14 C 0.3123(2) 0.21078(16) 0.39591(15) 0.0232(4) Uani 1 1 d . . .
C15 C 0.2906(2) 0.31856(16) 0.38966(15) 0.0231(4) Uani 1 1 d . . .
C16 C 0.1477(2) 0.34599(18) 0.40477(17) 0.0290(4) Uani 1 1 d . . .
H16 H 0.0627 0.2976 0.4191 0.035 Uiso 1 1 calc R . .
C17 C 0.1336(3) 0.4461(2) 0.39830(18) 0.0319(5) Uani 1 1 d . . .
H17 H 0.0380 0.4677 0.4085 0.038 Uiso 1 1 calc R . .
C18 C 0.2585(3) 0.51426(18) 0.37704(16) 0.0285(4) Uani 1 1 d . . .
H18 H 0.2509 0.5835 0.3730 0.034 Uiso 1 1 calc R . .
C19 C 0.3961(2) 0.47948(16) 0.36158(16) 0.0232(4) Uani 1 1 d . . .
C20 C 0.5329(2) 0.54873(16) 0.33391(16) 0.0244(4) Uani 1 1 d . . .
C21 C 0.7863(2) 0.53249(16) 0.27361(16) 0.0240(4) Uani 1 1 d . . .
C22 C 0.8721(3) 0.65173(17) 0.31239(18) 0.0295(4) Uani 1 1 d . . .
H22 H 0.8417 0.7111 0.3690 0.035 Uiso 1 1 calc R . .
C23 C 1.0006(3) 0.68407(19) 0.2693(2) 0.0353(5) Uani 1 1 d . . .
H23 H 1.0585 0.7655 0.2968 0.042 Uiso 1 1 calc R . .
C24 C 1.0455(3) 0.5986(2) 0.1861(2) 0.0358(5) Uani 1 1 d . . .
H24 H 1.1310 0.6211 0.1542 0.043 Uiso 1 1 calc R . .
C25 C 0.9651(3) 0.47994(19) 0.14971(18) 0.0309(4) Uani 1 1 d . . .
H25 H 0.9973 0.4212 0.0938 0.037 Uiso 1 1 calc R . .
C26 C 0.8381(2) 0.44611(16) 0.19399(16) 0.0245(4) Uani 1 1 d . . .
C27 C 0.7241(2) 0.26384(16) 0.21230(17) 0.0246(4) Uani 1 1 d . . .
C28 C 0.6635(3) 0.13051(18) 0.1460(2) 0.0394(5) Uani 1 1 d . . .
H28A H 0.7405 0.0988 0.1739 0.059 Uiso 1 1 calc R . .
H28B H 0.6547 0.1061 0.0644 0.059 Uiso 1 1 calc R . .
H28C H 0.5561 0.1001 0.1566 0.059 Uiso 1 1 calc R . .
O100 O 0.4918(2) 0.41500(14) 0.03915(15) 0.0437(4) Uani 1 1 d . . .
C100 C 0.3686(3) 0.4695(2) 0.0421(2) 0.0437(6) Uani 1 1 d . . .
H10A H 0.3218 0.4753 0.1077 0.052 Uiso 1 1 calc R . .
H10B H 0.2797 0.4208 -0.0293 0.052 Uiso 1 1 calc R . .
C101 C 0.5601(3) 0.4092(2) -0.0538(2) 0.0460(6) Uani 1 1 d . . .
H10C H 0.4743 0.3598 -0.1267 0.055 Uiso 1 1 calc R . .
H10D H 0.6464 0.3716 -0.0560 0.055 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
O1 C7 1.235(2) . ?
O2 C14 1.237(2) . ?
O3 C20 1.227(2) . ?
O4 C27 1.236(2) . ?
N1 C7 1.349(3) . ?
N1 C8 1.415(3) . ?
N1 H1N 0.84(2) . ?
N2 C14 1.350(2) . ?
N2 C13 1.426(2) . ?
N2 H2N 0.85(2) . ?
N3 C20 1.351(2) . ?
N3 C21 1.401(3) . ?
N3 H3N 0.80(2) . ?
N4 C27 1.347(3) . ?
N4 C26 1.432(2) . ?
N4 H4N 0.89(2) . ?
N5 C15 1.334(2) . ?
N5 C19 1.345(2) . ?
C1 C2 1.380(3) . ?
C1 C6 1.391(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.374(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.497(3) . ?
C8 C9 1.395(3) . ?
C8 C13 1.400(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.506(3) . ?
C15 C16 1.391(3) . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.504(3) . ?
C21 C22 1.397(3) . ?
C21 C26 1.404(3) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C27 C28 1.509(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
O100 C101 1.419(3) . ?
O100 C100 1.422(3) . ?
C100 C101 1.499(4) 2_665 ?
C100 H10A 0.9900 . ?
C100 H10B 0.9900 . ?
C101 C100 1.499(4) 2_665 ?
C101 H10C 0.9900 . ?
C101 H10D 0.9900 . ?

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
C7 N1 C8 124.69(17) . . ?
C7 N1 H1N 119.0(16) . . ?
C8 N1 H1N 114.7(16) . . ?
C14 N2 C13 127.54(17) . . ?
C14 N2 H2N 119.1(15) . . ?
C13 N2 H2N 112.9(15) . . ?
C20 N3 C21 127.54(17) . . ?
C20 N3 H3N 114.2(17) . . ?
C21 N3 H3N 118.3(17) . . ?
C27 N4 C26 127.19(17) . . ?
C27 N4 H4N 115.9(15) . . ?
C26 N4 H4N 116.1(15) . . ?
C15 N5 C19 118.09(16) . . ?
C2 C1 C6 120.5(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 118.2(2) . . ?
C1 C6 C7 123.12(19) . . ?
O1 C7 N1 122.13(19) . . ?
O1 C7 C6 122.38(18) . . ?
N1 C7 C6 115.49(17) . . ?
C9 C8 C13 119.26(19) . . ?
C9 C8 N1 121.01(17) . . ?
C13 C8 N1 119.72(17) . . ?
C10 C9 C8 120.49(19) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.13(19) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.79(19) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 119.51(17) . . ?
C12 C13 N2 118.23(17) . . ?
C8 C13 N2 122.14(18) . . ?
O2 C14 N2 125.27(18) . . ?
O2 C14 C15 120.37(17) . . ?
N2 C14 C15 114.34(16) . . ?
N5 C15 C16 123.22(18) . . ?
N5 C15 C14 116.76(16) . . ?
C16 C15 C14 120.01(18) . . ?
C17 C16 C15 117.84(19) . . ?
C17 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?
C18 C17 C16 119.83(18) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 118.51(18) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
N5 C19 C18 122.51(19) . . ?
N5 C19 C20 117.12(16) . . ?
C18 C19 C20 120.36(17) . . ?
O3 C20 N3 126.0(2) . . ?
O3 C20 C19 121.19(17) . . ?
N3 C20 C19 112.78(16) . . ?
C22 C21 N3 121.73(17) . . ?
C22 C21 C26 118.74(18) . . ?
N3 C21 C26 119.53(17) . . ?
C23 C22 C21 120.65(19) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.4(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C25 119.6(2) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.69(19) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C21 119.83(18) . . ?
C25 C26 N4 117.13(17) . . ?
C21 C26 N4 122.97(18) . . ?
O4 C27 N4 123.45(17) . . ?
O4 C27 C28 120.58(18) . . ?
N4 C27 C28 115.97(18) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C101 O100 C100 109.19(18) . . ?
O100 C100 C101 109.8(2) . 2_665 ?
O100 C100 H10A 109.7 . . ?
C101 C100 H10A 109.7 2_665 . ?
O100 C100 H10B 109.7 . . ?
C101 C100 H10B 109.7 2_665 . ?
H10A C100 H10B 108.2 . . ?
O100 C101 C100 110.82(19) . 2_665 ?
O100 C101 H10C 109.5 . . ?
C100 C101 H10C 109.5 2_665 . ?
O100 C101 H10D 109.5 . . ?
C100 C101 H10D 109.5 2_665 . ?
H10C C101 H10D 108.1 . . ?

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
C6 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C5 C6 C7 179.1(2) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C1 C6 C7 -178.6(2) . . . . ?
C8 N1 C7 O1 4.6(3) . . . . ?
C8 N1 C7 C6 -174.95(17) . . . . ?
C5 C6 C7 O1 -23.3(3) . . . . ?
C1 C6 C7 O1 155.9(2) . . . . ?
C5 C6 C7 N1 156.2(2) . . . . ?
C1 C6 C7 N1 -24.6(3) . . . . ?
C7 N1 C8 C9 -62.9(3) . . . . ?
C7 N1 C8 C13 117.7(2) . . . . ?
C13 C8 C9 C10 -2.9(3) . . . . ?
N1 C8 C9 C10 177.59(18) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 1.7(3) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C11 C12 C13 C8 -1.7(3) . . . . ?
C11 C12 C13 N2 -177.61(19) . . . . ?
C9 C8 C13 C12 3.6(3) . . . . ?
N1 C8 C13 C12 -176.92(17) . . . . ?
C9 C8 C13 N2 179.36(18) . . . . ?
N1 C8 C13 N2 -1.2(3) . . . . ?
C14 N2 C13 C12 -135.5(2) . . . . ?
C14 N2 C13 C8 48.7(3) . . . . ?
C13 N2 C14 O2 -3.8(3) . . . . ?
C13 N2 C14 C15 177.97(17) . . . . ?
C19 N5 C15 C16 0.8(3) . . . . ?
C19 N5 C15 C14 179.88(16) . . . . ?
O2 C14 C15 N5 -179.38(17) . . . . ?
N2 C14 C15 N5 -1.1(2) . . . . ?
O2 C14 C15 C16 -0.2(3) . . . . ?
N2 C14 C15 C16 178.05(17) . . . . ?
N5 C15 C16 C17 -1.0(3) . . . . ?
C14 C15 C16 C17 179.97(18) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C15 N5 C19 C18 0.1(3) . . . . ?
C15 N5 C19 C20 -178.46(16) . . . . ?
C17 C18 C19 N5 -0.7(3) . . . . ?
C17 C18 C19 C20 177.77(18) . . . . ?
C21 N3 C20 O3 -5.3(3) . . . . ?
C21 N3 C20 C19 173.94(17) . . . . ?
N5 C19 C20 O3 -176.65(17) . . . . ?
C18 C19 C20 O3 4.8(3) . . . . ?
N5 C19 C20 N3 4.0(2) . . . . ?
C18 C19 C20 N3 -174.56(17) . . . . ?
C20 N3 C21 C22 37.7(3) . . . . ?
C20 N3 C21 C26 -142.1(2) . . . . ?
N3 C21 C22 C23 -176.76(19) . . . . ?
C26 C21 C22 C23 3.0(3) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
C22 C23 C24 C25 -2.7(3) . . . . ?
C23 C24 C25 C26 1.3(3) . . . . ?
C24 C25 C26 C21 2.3(3) . . . . ?
C24 C25 C26 N4 179.33(19) . . . . ?
C22 C21 C26 C25 -4.4(3) . . . . ?
N3 C21 C26 C25 175.42(18) . . . . ?
C22 C21 C26 N4 178.73(18) . . . . ?
N3 C21 C26 N4 -1.5(3) . . . . ?
C27 N4 C26 C25 132.7(2) . . . . ?
C27 N4 C26 C21 -50.3(3) . . . . ?
C26 N4 C27 O4 7.7(3) . . . . ?
C26 N4 C27 C28 -171.72(19) . . . . ?
C101 O100 C100 C101 -58.3(3) . . . 2_665 ?
C100 O100 C101 C100 58.9(3) . . . 2_665 ?

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 O2 0.84(2) 1.96(2) 2.699(2) 146(2) .
N2 H2N O4 0.85(2) 2.21(2) 3.014(2) 157(2) .
N2 H2N N5 0.85(2) 2.28(2) 2.663(2) 107.6(18) .
N3 H3N O4 0.80(2) 2.03(2) 2.720(2) 143(2) .
N3 H3N N5 0.80(2) 2.19(2) 2.642(2) 116(2) .
N4 H4N O1 0.89(2) 1.98(2) 2.875(2) 177(2) 2_655

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.66
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_4-DMSO-S1
_database_code_depnum_ccdc_archive 'CCDC 1436672'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
N2-(2-acetamidophenyl)-N6-(2-benzamidophenyl)pyridine-2,6-dicarboxamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H23 N5 O4, 2(C2 H6 O S)'
_chemical_formula_sum            'C32 H35 N5 O6 S2'
_chemical_formula_weight         649.77

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'
S S 0.1246 0.1234 '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                   8.7246(5)
_cell_length_b                   13.2012(5)
_cell_length_c                   15.2754(5)
_cell_angle_alpha                97.888(3)
_cell_angle_beta                 104.934(4)
_cell_angle_gamma                104.062(4)
_cell_volume                     1611.07(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3871
_cell_measurement_theta_min      2.3670
_cell_measurement_theta_max      28.3180

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_T_min  0.82543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            11102
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.9141
_diffrn_reflns_theta_max         29.1393
_diffrn_measured_fraction_theta_max 0.8309
_diffrn_reflns_theta_full        26.3154
_diffrn_measured_fraction_theta_full 0.9904
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7198
_reflns_number_gt                5390
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.7451P] 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         7198
_refine_ls_number_parameters     464
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1271
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.2331(2) 0.43082(15) 0.17058(11) 0.0571(5) Uani 1 1 d . . . . .
O2 O 0.20203(18) 0.66933(11) 0.43342(10) 0.0344(3) Uani 1 1 d . . . . .
O3 O 0.5047(2) 1.18454(11) 0.35914(11) 0.0417(4) Uani 1 1 d . . . . .
O4 O 0.71414(17) 0.86575(10) 0.34413(9) 0.0307(3) Uani 1 1 d . . . . .
N1 N 0.2325(2) 0.51306(13) 0.31071(12) 0.0344(4) Uani 1 1 d D . . . .
H1N H 0.179(3) 0.5454(19) 0.3386(16) 0.052 Uiso 1 1 d D U . . .
N2 N 0.4428(2) 0.72562(13) 0.39636(12) 0.0283(4) Uani 1 1 d D . . . .
H2N H 0.508(3) 0.7795(15) 0.3869(16) 0.042 Uiso 1 1 d D U . . .
N3 N 0.6300(2) 1.05154(12) 0.34725(11) 0.0280(4) Uani 1 1 d D . . . .
H3N H 0.620(3) 0.9870(13) 0.3513(16) 0.042 Uiso 1 1 d D U . . .
N4 N 0.7405(2) 0.93076(12) 0.21699(11) 0.0289(4) Uani 1 1 d D . . . .
H4N H 0.730(3) 0.9140(18) 0.1596(11) 0.043 Uiso 1 1 d D U . . .
C1 C -0.0832(3) 0.4460(2) 0.08470(17) 0.0511(6) Uani 1 1 d . . . . .
H1 H -0.0178 0.4300 0.0467 0.061 Uiso 1 1 calc R U . . .
C2 C -0.2438(4) 0.4477(2) 0.04384(18) 0.0624(8) Uani 1 1 d . . . . .
H2 H -0.2869 0.4347 -0.0218 0.075 Uiso 1 1 calc R U . . .
C3 C -0.3407(3) 0.4684(2) 0.09832(18) 0.0527(6) Uani 1 1 d . . . . .
H3 H -0.4511 0.4688 0.0703 0.063 Uiso 1 1 calc R U . . .
C4 C -0.2775(3) 0.48860(19) 0.19345(17) 0.0459(6) Uani 1 1 d . . . . .
H4 H -0.3447 0.5025 0.2310 0.055 Uiso 1 1 calc R U . . .
N5 N 0.39809(19) 0.91834(12) 0.39153(10) 0.0242(3) Uani 1 1 d . . . . .
C5 C -0.1162(3) 0.48872(18) 0.23452(16) 0.0423(5) Uani 1 1 d . . . . .
H5 H -0.0731 0.5035 0.3002 0.051 Uiso 1 1 calc R U . . .
C6 C -0.0166(3) 0.46741(16) 0.18080(14) 0.0356(5) Uani 1 1 d . . . . .
C7 C 0.1602(3) 0.46827(16) 0.21966(15) 0.0370(5) Uani 1 1 d . . . . .
C8 C 0.4023(3) 0.53090(15) 0.35876(14) 0.0308(4) Uani 1 1 d . . . . .
C9 C 0.4692(3) 0.44572(16) 0.36508(15) 0.0379(5) Uani 1 1 d . . . . .
H9 H 0.3997 0.3747 0.3390 0.045 Uiso 1 1 calc R U . . .
C10 C 0.6356(3) 0.46357(18) 0.40883(15) 0.0415(6) Uani 1 1 d . . . . .
H10 H 0.6801 0.4049 0.4131 0.050 Uiso 1 1 calc R U . . .
C11 C 0.7378(3) 0.56675(18) 0.44653(15) 0.0388(5) Uani 1 1 d . . . . .
H11 H 0.8532 0.5791 0.4746 0.047 Uiso 1 1 calc R U . . .
C12 C 0.6718(3) 0.65221(17) 0.44335(14) 0.0340(5) Uani 1 1 d . . . . .
H12 H 0.7417 0.7229 0.4705 0.041 Uiso 1 1 calc R U . . .
C13 C 0.5034(3) 0.63464(15) 0.40043(13) 0.0280(4) Uani 1 1 d . . . . .
C14 C 0.3054(2) 0.73876(15) 0.41507(13) 0.0273(4) Uani 1 1 d . . . . .
C15 C 0.2803(2) 0.84662(15) 0.40984(12) 0.0258(4) Uani 1 1 d . . . . .
C16 C 0.1373(2) 0.86718(17) 0.42221(13) 0.0318(4) Uani 1 1 d . . . . .
H16 H 0.0543 0.8137 0.4335 0.038 Uiso 1 1 calc R U . . .
C17 C 0.1195(3) 0.96804(18) 0.41757(14) 0.0365(5) Uani 1 1 d . . . . .
H17 H 0.0237 0.9849 0.4259 0.044 Uiso 1 1 calc R U . . .
C18 C 0.2422(3) 1.04366(17) 0.40068(14) 0.0334(5) Uani 1 1 d . . . . .
H18 H 0.2335 1.1137 0.3987 0.040 Uiso 1 1 calc R U . . .
C19 C 0.3787(2) 1.01542(15) 0.38668(12) 0.0256(4) Uani 1 1 d . . . . .
C20 C 0.5108(2) 1.09359(15) 0.36318(13) 0.0279(4) Uani 1 1 d . . . . .
C21 C 0.7671(2) 1.10108(15) 0.32075(13) 0.0264(4) Uani 1 1 d . . . . .
C22 C 0.8513(3) 1.20966(15) 0.35493(14) 0.0319(4) Uani 1 1 d . . . . .
H22 H 0.8190 1.2504 0.3994 0.038 Uiso 1 1 calc R U . . .
C23 C 0.9807(3) 1.25805(16) 0.32460(15) 0.0367(5) Uani 1 1 d . . . . .
H23 H 1.0363 1.3321 0.3478 0.044 Uiso 1 1 calc R U . . .
C24 C 1.0305(3) 1.19968(17) 0.26056(15) 0.0361(5) Uani 1 1 d . . . . .
H24 H 1.1182 1.2338 0.2388 0.043 Uiso 1 1 calc R U . . .
C25 C 0.9519(3) 1.09152(16) 0.22850(14) 0.0321(4) Uani 1 1 d . . . . .
H25 H 0.9877 1.0511 0.1855 0.038 Uiso 1 1 calc R U . . .
C26 C 0.8214(2) 1.04098(14) 0.25816(13) 0.0263(4) Uani 1 1 d . . . . .
C27 C 0.6936(2) 0.85151(15) 0.25987(14) 0.0289(4) Uani 1 1 d . . . . .
C28 C 0.6132(3) 0.74208(17) 0.19787(17) 0.0477(6) Uani 1 1 d . . . . .
H28A H 0.5792 0.7488 0.1331 0.072 Uiso 0.5 1 calc R U P . .
H28B H 0.5157 0.7060 0.2143 0.072 Uiso 0.5 1 calc R U P . .
H28C H 0.6924 0.7001 0.2058 0.072 Uiso 0.5 1 calc R U P . .
H28D H 0.6123 0.6878 0.2357 0.072 Uiso 0.5 1 calc R U P . .
H28E H 0.6759 0.7306 0.1545 0.072 Uiso 0.5 1 calc R U P . .
H28F H 0.4991 0.7365 0.1630 0.072 Uiso 0.5 1 calc R U P . .
S11A S 0.43952(8) 0.19405(5) 0.04370(4) 0.03827(16) Uani 0.92 1 d . . P A 1
O11A O 0.2939(2) 0.10965(13) -0.02531(10) 0.0445(4) Uani 0.92 1 d . . P A 1
C11A C 0.3798(4) 0.2241(3) 0.14416(18) 0.0652(8) Uani 0.92 1 d . . P A 1
H11A H 0.3034 0.2677 0.1329 0.098 Uiso 0.92 1 calc R U P A 1
H11B H 0.4783 0.2637 0.1963 0.098 Uiso 0.92 1 calc R U P A 1
H11C H 0.3246 0.1575 0.1589 0.098 Uiso 0.92 1 calc R U P A 1
C12A C 0.5826(4) 0.1276(3) 0.0915(2) 0.0833(12) Uani 0.92 1 d . . P A 1
H12A H 0.5290 0.0715 0.1190 0.125 Uiso 0.92 1 calc R U P A 1
H12B H 0.6775 0.1789 0.1395 0.125 Uiso 0.92 1 calc R U P A 1
H12C H 0.6208 0.0953 0.0426 0.125 Uiso 0.92 1 calc R U P A 1
S11B S 0.420(4) 0.1094(13) 0.0788(17) 0.168(9) Uani 0.08 1 d . . P B 2
O11B O 0.2939(2) 0.10965(13) -0.02531(10) 0.0445(4) Uani 0.08 1 d . . P B 2
C11B C 0.3798(4) 0.2241(3) 0.14416(18) 0.0652(8) Uani 0.08 1 d . . P B 2
H11D H 0.2603 0.2097 0.1342 0.098 Uiso 0.08 1 calc R U P B 2
H11E H 0.4368 0.2343 0.2104 0.098 Uiso 0.08 1 calc R U P B 2
H11F H 0.4211 0.2888 0.1224 0.098 Uiso 0.08 1 calc R U P B 2
C12B C 0.5826(4) 0.1276(3) 0.0915(2) 0.0833(12) Uani 0.08 1 d . . P B 2
H12D H 0.6377 0.1247 0.1553 0.125 Uiso 0.08 1 calc R U P B 2
H12E H 0.6006 0.0729 0.0482 0.125 Uiso 0.08 1 calc R U P B 2
H12F H 0.6285 0.1984 0.0803 0.125 Uiso 0.08 1 calc R U P B 2
S21A S 0.1858(2) 0.88027(13) 0.13231(12) 0.0692(4) Uani 0.8 1 d . . P C 1
O21A O 0.3494(4) 0.8685(4) 0.1324(3) 0.1214(15) Uani 0.8 1 d . . P C 1
C21A C 0.0691(10) 0.8700(7) 0.0147(7) 0.0659(16) Uani 0.8 1 d . . P C 1
H21A H 0.0481 0.7979 -0.0211 0.099 Uiso 0.8 1 calc R U P C 1
H21B H 0.1319 0.9225 -0.0122 0.099 Uiso 0.8 1 calc R U P C 1
H21C H -0.0368 0.8840 0.0132 0.099 Uiso 0.8 1 calc R U P C 1
C22A C 0.0758(12) 0.7605(6) 0.1536(6) 0.109(3) Uani 0.8 1 d . . P C 1
H22A H 0.1223 0.7572 0.2184 0.163 Uiso 0.8 1 calc R U P C 1
H22B H 0.0849 0.6996 0.1127 0.163 Uiso 0.8 1 calc R U P C 1
H22C H -0.0411 0.7579 0.1415 0.163 Uiso 0.8 1 calc R U P C 1
S21B S 0.2187(11) 0.8512(7) 0.1100(5) 0.090(2) Uani 0.2 1 d . . P D 2
O21B O 0.2476(18) 0.9616(9) 0.1730(8) 0.104(5) Uani 0.2 1 d . . P D 2
C21B C 0.089(5) 0.845(3) 0.012(3) 0.0659(16) Uani 0.2 1 d . . P D 2
H21D H 0.1205 0.9130 -0.0081 0.099 Uiso 0.2 1 calc R U P D 2
H21E H -0.0226 0.8332 0.0180 0.099 Uiso 0.2 1 calc R U P D 2
H21F H 0.0903 0.7866 -0.0346 0.099 Uiso 0.2 1 calc R U P D 2
C22B C 0.043(4) 0.767(3) 0.140(2) 0.091(11) Uani 0.2 1 d . . P D 2
H22D H -0.0377 0.8068 0.1426 0.136 Uiso 0.2 1 calc R U P D 2
H22E H 0.0846 0.7498 0.1999 0.136 Uiso 0.2 1 calc R U P D 2
H22F H -0.0099 0.7014 0.0920 0.136 Uiso 0.2 1 calc R U P D 2


_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 C7 1.228(2) . ?
O2 C14 1.237(2) . ?
O3 C20 1.224(2) . ?
O4 C27 1.234(2) . ?
N1 C7 1.350(3) . ?
N1 C8 1.418(3) . ?
N1 H1N 0.854(16) . ?
N2 C14 1.347(2) . ?
N2 C13 1.428(2) . ?
N2 H2N 0.849(16) . ?
N3 C20 1.349(2) . ?
N3 C21 1.402(3) . ?
N3 H3N 0.848(16) . ?
N4 C27 1.345(2) . ?
N4 C26 1.425(2) . ?
N4 H4N 0.849(16) . ?
C1 C2 1.386(4) . ?
C1 C6 1.393(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.376(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
N5 C15 1.334(2) . ?
N5 C19 1.342(2) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.501(3) . ?
C8 C9 1.391(3) . ?
C8 C13 1.394(3) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.502(3) . ?
C15 C16 1.392(3) . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.503(3) . ?
C21 C22 1.397(3) . ?
C21 C26 1.406(3) . ?
C22 C23 1.378(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(3) . ?
C25 H25 0.9500 . ?
C27 C28 1.505(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C28 H28D 0.9800 . ?
C28 H28E 0.9800 . ?
C28 H28F 0.9800 . ?
S11A O11A 1.5053(16) . ?
S11A C12A 1.761(3) . ?
S11A C11A 1.769(3) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
S11B C12B 1.34(3) . ?
S11B O11B 1.68(3) . ?
S11B C11B 1.85(2) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
S21A O21A 1.472(4) . ?
S21A C22A 1.758(9) . ?
S21A C21A 1.790(10) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
S21B O21B 1.558(13) . ?
S21B C21B 1.61(4) . ?
S21B C22B 1.86(3) . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 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
C7 N1 C8 124.73(18) . . ?
C7 N1 H1N 117.6(17) . . ?
C8 N1 H1N 116.2(17) . . ?
C14 N2 C13 127.51(17) . . ?
C14 N2 H2N 117.2(16) . . ?
C13 N2 H2N 114.9(16) . . ?
C20 N3 C21 127.42(16) . . ?
C20 N3 H3N 117.5(16) . . ?
C21 N3 H3N 115.0(16) . . ?
C27 N4 C26 127.54(17) . . ?
C27 N4 H4N 117.8(16) . . ?
C26 N4 H4N 114.4(16) . . ?
C2 C1 C6 120.8(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C15 N5 C19 118.15(16) . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C7 124.2(2) . . ?
C1 C6 C7 117.5(2) . . ?
O1 C7 N1 122.9(2) . . ?
O1 C7 C6 121.3(2) . . ?
N1 C7 C6 115.82(18) . . ?
C9 C8 C13 119.5(2) . . ?
C9 C8 N1 120.63(19) . . ?
C13 C8 N1 119.86(18) . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 119.59(18) . . ?
C12 C13 N2 117.94(18) . . ?
C8 C13 N2 122.37(19) . . ?
O2 C14 N2 124.99(18) . . ?
O2 C14 C15 120.21(17) . . ?
N2 C14 C15 114.79(17) . . ?
N5 C15 C16 123.08(17) . . ?
N5 C15 C14 117.04(16) . . ?
C16 C15 C14 119.87(18) . . ?
C17 C16 C15 118.1(2) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C18 C17 C16 119.39(18) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 118.72(18) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
N5 C19 C18 122.55(19) . . ?
N5 C19 C20 117.02(16) . . ?
C18 C19 C20 120.41(17) . . ?
O3 C20 N3 125.9(2) . . ?
O3 C20 C19 121.34(18) . . ?
N3 C20 C19 112.72(15) . . ?
C22 C21 N3 121.38(17) . . ?
C22 C21 C26 118.92(18) . . ?
N3 C21 C26 119.69(17) . . ?
C23 C22 C21 120.50(19) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.55(19) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 119.5(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.93(19) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C21 119.48(17) . . ?
C25 C26 N4 117.15(17) . . ?
C21 C26 N4 123.19(17) . . ?
O4 C27 N4 123.28(18) . . ?
O4 C27 C28 121.32(18) . . ?
N4 C27 C28 115.41(18) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C28 H28D 109.5 . . ?
H28A C28 H28D 141.1 . . ?
H28B C28 H28D 56.3 . . ?
H28C C28 H28D 56.3 . . ?
C27 C28 H28E 109.5 . . ?
H28A C28 H28E 56.3 . . ?
H28B C28 H28E 141.1 . . ?
H28C C28 H28E 56.3 . . ?
H28D C28 H28E 109.5 . . ?
C27 C28 H28F 109.5 . . ?
H28A C28 H28F 56.3 . . ?
H28B C28 H28F 56.3 . . ?
H28C C28 H28F 141.1 . . ?
H28D C28 H28F 109.5 . . ?
H28E C28 H28F 109.5 . . ?
O11A S11A C12A 106.38(14) . . ?
O11A S11A C11A 106.66(13) . . ?
C12A S11A C11A 96.61(16) . . ?
S11A C11A H11A 109.5 . . ?
S11A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
S11A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
S11A C12A H12A 109.5 . . ?
S11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
S11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C12B S11B O11B 119.7(15) . . ?
C12B S11B C11B 110.3(13) . . ?
O11B S11B C11B 96.0(12) . . ?
S11B C11B H11D 109.5 . . ?
S11B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
S11B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
S11B C12B H12D 109.5 . . ?
S11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
S11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
O21A S21A C22A 106.3(4) . . ?
O21A S21A C21A 107.8(3) . . ?
C22A S21A C21A 100.2(4) . . ?
S21A C21A H21A 109.5 . . ?
S21A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
S21A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
S21A C22A H22A 109.5 . . ?
S21A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
S21A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
O21B S21B C21B 107.3(15) . . ?
O21B S21B C22B 100.9(14) . . ?
C21B S21B C22B 88(2) . . ?
S21B C21B H21D 109.5 . . ?
S21B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
S21B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
S21B C22B H22D 109.5 . . ?
S21B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
S21B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 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
C6 C1 C2 C3 -1.5(4) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 178.6(2) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C2 C1 C6 C7 -177.6(2) . . . . ?
C8 N1 C7 O1 5.7(3) . . . . ?
C8 N1 C7 C6 -173.84(18) . . . . ?
C5 C6 C7 O1 166.9(2) . . . . ?
C1 C6 C7 O1 -14.5(3) . . . . ?
C5 C6 C7 N1 -13.5(3) . . . . ?
C1 C6 C7 N1 165.1(2) . . . . ?
C7 N1 C8 C9 -61.3(3) . . . . ?
C7 N1 C8 C13 118.9(2) . . . . ?
C13 C8 C9 C10 -2.7(3) . . . . ?
N1 C8 C9 C10 177.58(19) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 2.4(3) . . . . ?
C10 C11 C12 C13 -1.5(3) . . . . ?
C11 C12 C13 C8 -1.5(3) . . . . ?
C11 C12 C13 N2 -177.95(18) . . . . ?
C9 C8 C13 C12 3.6(3) . . . . ?
N1 C8 C13 C12 -176.67(18) . . . . ?
C9 C8 C13 N2 179.82(17) . . . . ?
N1 C8 C13 N2 -0.4(3) . . . . ?
C14 N2 C13 C12 -134.7(2) . . . . ?
C14 N2 C13 C8 49.0(3) . . . . ?
C13 N2 C14 O2 -5.0(3) . . . . ?
C13 N2 C14 C15 176.56(17) . . . . ?
C19 N5 C15 C16 1.3(3) . . . . ?
C19 N5 C15 C14 -179.86(15) . . . . ?
O2 C14 C15 N5 178.73(17) . . . . ?
N2 C14 C15 N5 -2.8(2) . . . . ?
O2 C14 C15 C16 -2.4(3) . . . . ?
N2 C14 C15 C16 176.05(17) . . . . ?
N5 C15 C16 C17 -1.7(3) . . . . ?
C14 C15 C16 C17 179.50(17) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 1.5(3) . . . . ?
C15 N5 C19 C18 0.5(3) . . . . ?
C15 N5 C19 C20 -178.25(16) . . . . ?
C17 C18 C19 N5 -1.9(3) . . . . ?
C17 C18 C19 C20 176.81(18) . . . . ?
C21 N3 C20 O3 -1.8(3) . . . . ?
C21 N3 C20 C19 177.64(17) . . . . ?
N5 C19 C20 O3 -178.52(17) . . . . ?
C18 C19 C20 O3 2.7(3) . . . . ?
N5 C19 C20 N3 2.0(2) . . . . ?
C18 C19 C20 N3 -176.82(17) . . . . ?
C20 N3 C21 C22 36.7(3) . . . . ?
C20 N3 C21 C26 -143.00(19) . . . . ?
N3 C21 C22 C23 -176.83(18) . . . . ?
C26 C21 C22 C23 2.9(3) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C25 -1.4(3) . . . . ?
C23 C24 C25 C26 1.3(3) . . . . ?
C24 C25 C26 C21 0.9(3) . . . . ?
C24 C25 C26 N4 176.03(18) . . . . ?
C22 C21 C26 C25 -2.9(3) . . . . ?
N3 C21 C26 C25 176.75(17) . . . . ?
C22 C21 C26 N4 -177.79(18) . . . . ?
N3 C21 C26 N4 1.9(3) . . . . ?
C27 N4 C26 C25 136.2(2) . . . . ?
C27 N4 C26 C21 -48.8(3) . . . . ?
C26 N4 C27 O4 1.0(3) . . . . ?
C26 N4 C27 C28 -178.87(19) . . . . ?

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 O2 0.854(16) 1.96(2) 2.702(2) 144(2) .
N2 H2N O4 0.849(16) 2.187(18) 2.986(2) 157(2) .
N2 H2N N5 0.849(16) 2.26(2) 2.674(2) 109.7(18) .
N3 H3N O4 0.848(16) 1.970(18) 2.724(2) 148(2) .
N3 H3N N5 0.848(16) 2.21(2) 2.635(2) 111.2(18) .
N4 H4N O11A 0.849(16) 1.980(16) 2.826(2) 174(2) 2_665

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_4-Form-II-S1
_database_code_depnum_ccdc_archive 'CCDC 1436673'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H23 N5 O4'
_chemical_formula_sum            'C28 H23 N5 O4'
_chemical_formula_weight         493.51

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   26.4407(11)
_cell_length_b                   8.6348(3)
_cell_length_c                   21.4502(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.284(2)
_cell_angle_gamma                90.00
_cell_volume                     4883.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2064
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8394
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_process_details   
;
Denzo (otwinowski, Borek, Majewski & Minor, 2003) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KappaCCD, Cu, APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6571
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         67.00
_reflns_number_total             4156
_reflns_number_gt                2796
_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)+(0.0516P)²+3.0661P] 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         4156
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
O1 O -0.00656(7) 0.1788(2) 1.13278(10) 0.0567(5) Uani 1 1 d . . .
O2 O 0.15347(7) 0.4194(2) 1.14495(9) 0.0471(5) Uani 1 1 d . . .
O3 O 0.22157(8) 0.2509(2) 0.84172(9) 0.0637(6) Uani 1 1 d . . .
O4 O 0.15591(6) -0.08070(19) 1.00832(7) 0.0392(4) Uani 1 1 d . . .
N1 N 0.06749(8) 0.2790(3) 1.17325(11) 0.0445(6) Uani 1 1 d . . .
H1N H 0.0883(11) 0.360(3) 1.1720(13) 0.053 Uiso 1 1 d . . .
N2 N 0.14827(8) 0.1769(2) 1.10186(10) 0.0389(5) Uani 1 1 d . . .
H2N H 0.1584(10) 0.123(3) 1.0699(13) 0.047 Uiso 1 1 d . . .
N3 N 0.18996(8) 0.0718(3) 0.90761(10) 0.0426(6) Uani 1 1 d . . .
H3N H 0.1804(11) 0.065(3) 0.9453(14) 0.051 Uiso 1 1 d . . .
N4 N 0.10783(8) -0.1369(2) 0.91900(10) 0.0398(5) Uani 1 1 d . . .
H4N H 0.0785(11) -0.165(3) 0.9045(13) 0.048 Uiso 1 1 d . . .
N5 N 0.18421(7) 0.2820(2) 0.99668(9) 0.0374(5) Uani 1 1 d . . .
C1 C 0.01886(12) 0.5803(3) 1.16654(15) 0.0565(8) Uani 1 1 d . . .
H1 H 0.0431 0.5667 1.2010 0.068 Uiso 1 1 calc R . .
C2 C -0.00021(13) 0.7264(4) 1.15234(17) 0.0666(9) Uani 1 1 d . . .
H2 H 0.0108 0.8122 1.1775 0.080 Uiso 1 1 calc R . .
C3 C -0.03466(12) 0.7485(4) 1.10255(16) 0.0613(8) Uani 1 1 d . . .
H3 H -0.0478 0.8490 1.0934 0.074 Uiso 1 1 calc R . .
C4 C -0.05012(13) 0.6253(4) 1.06587(16) 0.0648(9) Uani 1 1 d . . .
H4 H -0.0738 0.6405 1.0309 0.078 Uiso 1 1 calc R . .
C5 C -0.03144(12) 0.4786(4) 1.07956(15) 0.0606(8) Uani 1 1 d . . .
H5 H -0.0422 0.3940 1.0535 0.073 Uiso 1 1 calc R . .
C6 C 0.00265(10) 0.4534(3) 1.13058(12) 0.0421(6) Uani 1 1 d . . .
C7 C 0.02041(10) 0.2922(3) 1.14540(12) 0.0422(6) Uani 1 1 d . . .
C8 C 0.09230(10) 0.1357(3) 1.18698(12) 0.0400(6) Uani 1 1 d . . .
C9 C 0.07822(10) 0.0434(3) 1.23585(13) 0.0489(7) Uani 1 1 d . . .
H9 H 0.0519 0.0768 1.2606 0.059 Uiso 1 1 calc R . .
C10 C 0.10198(11) -0.0954(4) 1.24872(13) 0.0526(7) Uani 1 1 d . . .
H10 H 0.0920 -0.1577 1.2822 0.063 Uiso 1 1 calc R . .
C11 C 0.14042(11) -0.1453(3) 1.21327(13) 0.0494(7) Uani 1 1 d . . .
H11 H 0.1563 -0.2424 1.2219 0.059 Uiso 1 1 calc R . .
C12 C 0.15558(10) -0.0538(3) 1.16548(12) 0.0443(7) Uani 1 1 d . . .
H12 H 0.1822 -0.0876 1.1414 0.053 Uiso 1 1 calc R . .
C13 C 0.13203(9) 0.0880(3) 1.15233(11) 0.0378(6) Uani 1 1 d . . .
C14 C 0.15930(9) 0.3297(3) 1.10161(12) 0.0383(6) Uani 1 1 d . . .
C15 C 0.17896(9) 0.3868(3) 1.04177(12) 0.0381(6) Uani 1 1 d . . .
C16 C 0.18986(10) 0.5428(3) 1.03505(14) 0.0492(7) Uani 1 1 d . . .
H16 H 0.1847 0.6146 1.0675 0.059 Uiso 1 1 calc R . .
C17 C 0.20848(11) 0.5905(3) 0.97970(14) 0.0528(8) Uani 1 1 d . . .
H17 H 0.2164 0.6964 0.9736 0.063 Uiso 1 1 calc R . .
C18 C 0.21548(10) 0.4840(3) 0.93344(14) 0.0484(7) Uani 1 1 d . . .
H18 H 0.2292 0.5145 0.8956 0.058 Uiso 1 1 calc R . .
C19 C 0.20210(9) 0.3311(3) 0.94327(12) 0.0390(6) Uani 1 1 d . . .
C20 C 0.20590(10) 0.2143(3) 0.89167(12) 0.0442(7) Uani 1 1 d . . .
C21 C 0.18604(10) -0.0616(3) 0.87006(11) 0.0405(6) Uani 1 1 d . . .
C22 C 0.22099(11) -0.0932(4) 0.82580(12) 0.0510(7) Uani 1 1 d . . .
H22 H 0.2488 -0.0254 0.8216 0.061 Uiso 1 1 calc R . .
C23 C 0.21505(13) -0.2227(4) 0.78833(13) 0.0578(8) Uani 1 1 d . . .
H23 H 0.2384 -0.2423 0.7577 0.069 Uiso 1 1 calc R . .
C24 C 0.17540(13) -0.3243(4) 0.79490(12) 0.0560(8) Uani 1 1 d . . .
H24 H 0.1716 -0.4134 0.7690 0.067 Uiso 1 1 calc R . .
C25 C 0.14118(12) -0.2957(3) 0.83928(12) 0.0497(7) Uani 1 1 d . . .
H25 H 0.1140 -0.3657 0.8440 0.060 Uiso 1 1 calc R . .
C26 C 0.14655(10) -0.1649(3) 0.87687(11) 0.0391(6) Uani 1 1 d . . .
C27 C 0.11396(9) -0.1041(3) 0.98050(12) 0.0373(6) Uani 1 1 d . . .
C28 C 0.06624(10) -0.0968(4) 1.01443(14) 0.0539(7) Uani 1 1 d . . .
H28A H 0.0665 -0.1805 1.0453 0.081 Uiso 1 1 calc R . .
H28B H 0.0367 -0.1084 0.9844 0.081 Uiso 1 1 calc R . .
H28C H 0.0645 0.0033 1.0357 0.081 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
O1 C7 1.230(3) . ?
O2 C14 1.228(3) . ?
O3 C20 1.219(3) . ?
O4 C27 1.236(3) . ?
N1 C7 1.345(3) . ?
N1 C8 1.421(3) . ?
N1 H1N 0.89(3) . ?
N2 C14 1.351(3) . ?
N2 C13 1.420(3) . ?
N2 H2N 0.89(3) . ?
N3 C20 1.353(3) . ?
N3 C21 1.405(3) . ?
N3 H3N 0.87(3) . ?
N4 C27 1.347(3) . ?
N4 C26 1.436(3) . ?
N4 H4N 0.85(3) . ?
N5 C15 1.339(3) . ?
N5 C19 1.341(3) . ?
C1 C2 1.384(4) . ?
C1 C6 1.389(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.364(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.368(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.496(4) . ?
C8 C9 1.390(4) . ?
C8 C13 1.394(4) . ?
C9 C10 1.372(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(4) . ?
C12 H12 0.9500 . ?
C14 C15 1.503(4) . ?
C15 C16 1.387(4) . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.375(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.506(4) . ?
C21 C26 1.389(4) . ?
C21 C22 1.400(4) . ?
C22 C23 1.379(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(4) . ?
C25 H25 0.9500 . ?
C27 C28 1.504(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
C7 N1 C8 124.3(2) . . ?
C7 N1 H1N 118.2(19) . . ?
C8 N1 H1N 114.5(18) . . ?
C14 N2 C13 127.5(2) . . ?
C14 N2 H2N 115.6(18) . . ?
C13 N2 H2N 115.6(18) . . ?
C20 N3 C21 127.7(2) . . ?
C20 N3 H3N 114.4(19) . . ?
C21 N3 H3N 117.8(19) . . ?
C27 N4 C26 127.8(2) . . ?
C27 N4 H4N 117.3(19) . . ?
C26 N4 H4N 113.4(19) . . ?
C15 N5 C19 117.8(2) . . ?
C2 C1 C6 120.3(3) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.1(3) . . ?
C5 C6 C7 119.4(2) . . ?
C1 C6 C7 122.5(2) . . ?
O1 C7 N1 122.2(3) . . ?
O1 C7 C6 121.8(2) . . ?
N1 C7 C6 116.0(2) . . ?
C9 C8 C13 119.2(2) . . ?
C9 C8 N1 120.7(2) . . ?
C13 C8 N1 120.1(2) . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 119.7(2) . . ?
C12 C13 N2 118.3(2) . . ?
C8 C13 N2 122.0(2) . . ?
O2 C14 N2 125.0(3) . . ?
O2 C14 C15 120.7(2) . . ?
N2 C14 C15 114.3(2) . . ?
N5 C15 C16 123.2(3) . . ?
N5 C15 C14 117.1(2) . . ?
C16 C15 C14 119.6(3) . . ?
C17 C16 C15 117.9(3) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 118.5(3) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
N5 C19 C18 122.8(3) . . ?
N5 C19 C20 117.6(2) . . ?
C18 C19 C20 119.6(2) . . ?
O3 C20 N3 126.2(3) . . ?
O3 C20 C19 121.2(3) . . ?
N3 C20 C19 112.6(2) . . ?
C26 C21 C22 119.0(3) . . ?
C26 C21 N3 119.3(2) . . ?
C22 C21 N3 121.6(3) . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C25 119.8(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C21 C26 C25 120.4(2) . . ?
C21 C26 N4 122.4(2) . . ?
C25 C26 N4 117.1(2) . . ?
O4 C27 N4 123.0(2) . . ?
O4 C27 C28 121.0(2) . . ?
N4 C27 C28 116.0(2) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C6 C1 C2 C3 -0.8(5) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C4 C5 C6 C1 -2.0(5) . . . . ?
C4 C5 C6 C7 177.6(3) . . . . ?
C2 C1 C6 C5 2.1(5) . . . . ?
C2 C1 C6 C7 -177.5(3) . . . . ?
C8 N1 C7 O1 4.6(4) . . . . ?
C8 N1 C7 C6 -175.4(2) . . . . ?
C5 C6 C7 O1 -30.2(4) . . . . ?
C1 C6 C7 O1 149.4(3) . . . . ?
C5 C6 C7 N1 149.9(3) . . . . ?
C1 C6 C7 N1 -30.6(4) . . . . ?
C7 N1 C8 C9 -74.1(3) . . . . ?
C7 N1 C8 C13 107.5(3) . . . . ?
C13 C8 C9 C10 -2.1(4) . . . . ?
N1 C8 C9 C10 179.5(2) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C11 C12 C13 C8 -1.3(4) . . . . ?
C11 C12 C13 N2 -178.8(2) . . . . ?
C9 C8 C13 C12 2.6(4) . . . . ?
N1 C8 C13 C12 -179.0(2) . . . . ?
C9 C8 C13 N2 -180.0(2) . . . . ?
N1 C8 C13 N2 -1.6(3) . . . . ?
C14 N2 C13 C12 -133.1(3) . . . . ?
C14 N2 C13 C8 49.4(3) . . . . ?
C13 N2 C14 O2 -5.4(4) . . . . ?
C13 N2 C14 C15 176.0(2) . . . . ?
C19 N5 C15 C16 1.7(3) . . . . ?
C19 N5 C15 C14 -179.5(2) . . . . ?
O2 C14 C15 N5 -179.9(2) . . . . ?
N2 C14 C15 N5 -1.2(3) . . . . ?
O2 C14 C15 C16 -1.0(3) . . . . ?
N2 C14 C15 C16 177.7(2) . . . . ?
N5 C15 C16 C17 -2.0(4) . . . . ?
C14 C15 C16 C17 179.2(2) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 1.8(4) . . . . ?
C15 N5 C19 C18 0.5(3) . . . . ?
C15 N5 C19 C20 -177.5(2) . . . . ?
C17 C18 C19 N5 -2.2(4) . . . . ?
C17 C18 C19 C20 175.7(2) . . . . ?
C21 N3 C20 O3 -2.8(4) . . . . ?
C21 N3 C20 C19 176.7(2) . . . . ?
N5 C19 C20 O3 179.6(2) . . . . ?
C18 C19 C20 O3 1.6(4) . . . . ?
N5 C19 C20 N3 0.1(3) . . . . ?
C18 C19 C20 N3 -177.9(2) . . . . ?
C20 N3 C21 C26 -144.5(3) . . . . ?
C20 N3 C21 C22 35.4(4) . . . . ?
C26 C21 C22 C23 2.1(4) . . . . ?
N3 C21 C22 C23 -177.9(2) . . . . ?
C21 C22 C23 C24 -1.5(4) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C23 C24 C25 C26 0.3(4) . . . . ?
C22 C21 C26 C25 -1.5(4) . . . . ?
N3 C21 C26 C25 178.5(2) . . . . ?
C22 C21 C26 N4 -176.9(2) . . . . ?
N3 C21 C26 N4 3.1(4) . . . . ?
C24 C25 C26 C21 0.3(4) . . . . ?
C24 C25 C26 N4 175.9(2) . . . . ?
C27 N4 C26 C21 -53.6(4) . . . . ?
C27 N4 C26 C25 130.8(3) . . . . ?
C26 N4 C27 O4 6.3(4) . . . . ?
C26 N4 C27 C28 -173.8(2) . . . . ?

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 O2 0.89(3) 1.93(3) 2.686(3) 142(3) .
N2 H2N O4 0.89(3) 2.20(3) 3.013(3) 153(2) .
N2 H2N N5 0.89(3) 2.23(3) 2.671(3) 110(2) .
N3 H3N O4 0.87(3) 1.99(3) 2.739(3) 144(3) .
N3 H3N N5 0.87(3) 2.17(3) 2.648(3) 114(2) .
N4 H4N O1 0.85(3) 2.01(3) 2.844(3) 167(3) 5_557

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_6-Diox-S2
_database_code_depnum_ccdc_archive 'CCDC 1436674'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H29 N5 O4, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C33 H33 N5 O5'
_chemical_formula_weight         579.64

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                   9.6881(6)
_cell_length_b                   10.6294(7)
_cell_length_c                   15.8346(9)
_cell_angle_alpha                105.487(5)
_cell_angle_beta                 103.244(5)
_cell_angle_gamma                102.241(5)
_cell_volume                     1463.30(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2857
_cell_measurement_theta_min      2.5730
_cell_measurement_theta_max      27.4480

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_T_min  0.98614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            10347
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.0782
_diffrn_reflns_theta_max         29.2023
_diffrn_measured_fraction_theta_max 0.8320
_diffrn_reflns_theta_full        26.3154
_diffrn_measured_fraction_theta_full 0.9915
_reflns_number_total             6610
_reflns_number_gt                4520
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0255P)²+0.6205P] 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         6610
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.21070(15) 0.37671(13) 0.18464(10) 0.0265(3) Uani 1 1 d . . . . .
O2 O 0.07723(17) -0.09914(15) 0.18762(11) 0.0400(4) Uani 1 1 d . . . . .
O3 O 0.75639(15) 0.39459(14) 0.29074(10) 0.0310(4) Uani 1 1 d . . . . .
O4 O 0.74283(18) 0.86779(15) 0.44285(10) 0.0394(4) Uani 1 1 d . . . . .
N1 N -0.01662(19) 0.34095(17) 0.20588(12) 0.0252(4) Uani 1 1 d . . . . .
H1N H -0.077(2) 0.380(2) 0.2345(15) 0.038 Uiso 1 1 d . U . . .
N2 N 0.10143(19) 0.11206(17) 0.17270(12) 0.0248(4) Uani 1 1 d . . . . .
H2N H 0.168(2) 0.188(2) 0.1818(15) 0.037 Uiso 1 1 d . U . . .
N3 N 0.53000(19) 0.42193(17) 0.23392(12) 0.0247(4) Uani 1 1 d . . . . .
H3N H 0.438(3) 0.380(2) 0.2158(15) 0.037 Uiso 1 1 d . U . . .
N4 N 0.75508(19) 0.66147(17) 0.36300(12) 0.0254(4) Uani 1 1 d . . . . .
H4N H 0.778(2) 0.587(2) 0.3657(15) 0.038 Uiso 1 1 d . U . . .
N5 N 0.39322(18) 0.17815(16) 0.23618(11) 0.0228(4) Uani 1 1 d . . . . .
C1 C 0.3137(2) 0.6141(2) 0.34841(15) 0.0320(5) Uani 1 1 d . . . . .
H1 H 0.3831 0.5640 0.3417 0.038 Uiso 1 1 calc R U . . .
C2 C 0.3592(3) 0.7425(2) 0.41319(16) 0.0386(6) Uani 1 1 d . . . . .
H2 H 0.4592 0.7797 0.4515 0.046 Uiso 1 1 calc R U . . .
C3 C 0.2595(3) 0.8173(2) 0.42251(16) 0.0371(6) Uani 1 1 d . . . . .
H3 H 0.2904 0.9054 0.4676 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1152(3) 0.7630(2) 0.36604(17) 0.0370(6) Uani 1 1 d . . . . .
H4 H 0.0471 0.8149 0.3714 0.044 Uiso 1 1 calc R U . . .
C5 C 0.0687(2) 0.6338(2) 0.30170(15) 0.0310(5) Uani 1 1 d . . . . .
H5 H -0.0312 0.5972 0.2633 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1675(2) 0.5572(2) 0.29280(14) 0.0237(4) Uani 1 1 d . . . . .
C7 C 0.1228(2) 0.4182(2) 0.22289(13) 0.0231(4) Uani 1 1 d . . . . .
C8 C -0.0954(2) 0.2134(2) 0.13444(14) 0.0259(5) Uani 1 1 d . . . . .
C9 C -0.2341(2) 0.2037(2) 0.07971(15) 0.0342(5) Uani 1 1 d . . . . .
H9 H -0.2696 0.2815 0.0886 0.041 Uiso 1 1 calc R U . . .
C10 C -0.3209(2) 0.0821(2) 0.01249(15) 0.0387(6) Uani 1 1 d . . . . .
H10 H -0.4152 0.0765 -0.0252 0.046 Uiso 1 1 calc R U . . .
C11 C -0.2700(3) -0.0316(2) 0.00022(15) 0.0376(6) Uani 1 1 d . . . . .
H11 H -0.3304 -0.1159 -0.0452 0.045 Uiso 1 1 calc R U . . .
C12 C -0.1321(2) -0.0231(2) 0.05351(14) 0.0313(5) Uani 1 1 d . . . . .
H12 H -0.0975 -0.1015 0.0443 0.038 Uiso 1 1 calc R U . . .
C13 C -0.0431(2) 0.0994(2) 0.12087(14) 0.0249(5) Uani 1 1 d . . . . .
C14 C 0.1530(2) 0.0134(2) 0.19579(14) 0.0268(5) Uani 1 1 d . . . . .
C15 C 0.3196(2) 0.0574(2) 0.23737(13) 0.0247(5) Uani 1 1 d . . . . .
C16 C 0.3889(3) -0.0253(2) 0.27453(15) 0.0322(5) Uani 1 1 d . . . . .
H16 H 0.3332 -0.1115 0.2729 0.039 Uiso 1 1 calc R U . . .
C17 C 0.5413(3) 0.0205(2) 0.31410(16) 0.0381(6) Uani 1 1 d . . . . .
H17 H 0.5918 -0.0327 0.3418 0.046 Uiso 1 1 calc R U . . .
C18 C 0.6190(2) 0.1447(2) 0.31274(15) 0.0336(5) Uani 1 1 d . . . . .
H18 H 0.7237 0.1779 0.3387 0.040 Uiso 1 1 calc R U . . .
C19 C 0.5406(2) 0.2199(2) 0.27263(13) 0.0244(4) Uani 1 1 d . . . . .
C20 C 0.6193(2) 0.3535(2) 0.26663(14) 0.0242(5) Uani 1 1 d . . . . .
C21 C 0.5733(2) 0.5432(2) 0.21201(14) 0.0244(4) Uani 1 1 d . . . . .
C22 C 0.4946(2) 0.5456(2) 0.12797(15) 0.0338(5) Uani 1 1 d . . . . .
H22 H 0.4169 0.4673 0.0870 0.041 Uiso 1 1 calc R U . . .
C23 C 0.5280(3) 0.6608(2) 0.10304(16) 0.0415(6) Uani 1 1 d . . . . .
H23 H 0.4719 0.6627 0.0460 0.050 Uiso 1 1 calc R U . . .
C24 C 0.6437(3) 0.7731(2) 0.16178(16) 0.0395(6) Uani 1 1 d . . . . .
H24 H 0.6700 0.8512 0.1439 0.047 Uiso 1 1 calc R U . . .
C25 C 0.7213(2) 0.7725(2) 0.24649(15) 0.0317(5) Uani 1 1 d . . . . .
H25 H 0.8009 0.8501 0.2864 0.038 Uiso 1 1 calc R U . . .
C26 C 0.6839(2) 0.6591(2) 0.27368(14) 0.0242(4) Uani 1 1 d . . . . .
C27 C 0.7783(2) 0.7640(2) 0.44230(14) 0.0256(5) Uani 1 1 d . . . . .
C28 C 0.8446(2) 0.7398(2) 0.53230(14) 0.0278(5) Uani 1 1 d . . . . .
C29 C 0.9577(3) 0.8734(2) 0.59904(16) 0.0424(6) Uani 1 1 d . . . . .
H29A H 1.0377 0.8990 0.5731 0.064 Uiso 1 1 calc R U . . .
H29B H 0.9988 0.8612 0.6579 0.064 Uiso 1 1 calc R U . . .
H29C H 0.9088 0.9456 0.6088 0.064 Uiso 1 1 calc R U . . .
C30 C 0.9192(3) 0.6258(2) 0.52118(16) 0.0405(6) Uani 1 1 d . . . . .
H30A H 0.8451 0.5387 0.4827 0.061 Uiso 1 1 calc R U . . .
H30B H 0.9638 0.6204 0.5818 0.061 Uiso 1 1 calc R U . . .
H30C H 0.9964 0.6453 0.4920 0.061 Uiso 1 1 calc R U . . .
C31 C 0.7149(3) 0.7023(2) 0.56994(16) 0.0417(6) Uani 1 1 d . . . . .
H31A H 0.6665 0.7750 0.5771 0.063 Uiso 1 1 calc R U . . .
H31B H 0.7520 0.6915 0.6298 0.063 Uiso 1 1 calc R U . . .
H31C H 0.6432 0.6165 0.5270 0.063 Uiso 1 1 calc R U . . .
O100 O 0.8697(2) 0.46073(16) 0.02474(12) 0.0515(5) Uani 1 1 d . . . . .
C100 C 0.9439(3) 0.6006(2) 0.04276(17) 0.0475(7) Uani 1 1 d . . . . .
H10A H 0.9300 0.6577 0.0990 0.057 Uiso 1 1 calc R U . . .
H10B H 0.9002 0.6296 -0.0091 0.057 Uiso 1 1 calc R U . . .
C101 C 0.8936(3) 0.3782(2) -0.05533(17) 0.0493(7) Uani 1 1 d . . . . .
H10C H 0.8488 0.4022 -0.1094 0.059 Uiso 1 1 calc R U . . .
H10D H 0.8446 0.2808 -0.0671 0.059 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 C7 1.241(2) . ?
O2 C14 1.220(2) . ?
O3 C20 1.238(2) . ?
O4 C27 1.222(2) . ?
N1 C7 1.348(2) . ?
N1 C8 1.431(3) . ?
N1 H1N 0.92(2) . ?
N2 C14 1.352(3) . ?
N2 C13 1.409(2) . ?
N2 H2N 0.87(2) . ?
N3 C20 1.345(3) . ?
N3 C21 1.426(3) . ?
N3 H3N 0.85(2) . ?
N4 C27 1.360(2) . ?
N4 C26 1.415(3) . ?
N4 H4N 0.87(2) . ?
N5 C19 1.336(2) . ?
N5 C15 1.337(2) . ?
C1 C2 1.378(3) . ?
C1 C6 1.389(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.493(3) . ?
C8 C9 1.388(3) . ?
C8 C13 1.393(3) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.512(3) . ?
C15 C16 1.385(3) . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.501(3) . ?
C21 C22 1.384(3) . ?
C21 C26 1.392(3) . ?
C22 C23 1.381(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(3) . ?
C25 H25 0.9500 . ?
C27 C28 1.535(3) . ?
C28 C30 1.528(3) . ?
C28 C29 1.531(3) . ?
C28 C31 1.533(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O100 C100 1.427(3) . ?
O100 C101 1.435(3) . ?
C100 C101 1.500(4) 2_765 ?
C100 H10A 0.9900 . ?
C100 H10B 0.9900 . ?
C101 C100 1.500(4) 2_765 ?
C101 H10C 0.9900 . ?
C101 H10D 0.9900 . ?

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
C7 N1 C8 127.93(18) . . ?
C7 N1 H1N 117.9(14) . . ?
C8 N1 H1N 112.9(14) . . ?
C14 N2 C13 127.56(18) . . ?
C14 N2 H2N 116.4(15) . . ?
C13 N2 H2N 115.0(15) . . ?
C20 N3 C21 126.95(18) . . ?
C20 N3 H3N 114.9(15) . . ?
C21 N3 H3N 117.2(15) . . ?
C27 N4 C26 125.10(17) . . ?
C27 N4 H4N 119.4(15) . . ?
C26 N4 H4N 115.3(15) . . ?
C19 N5 C15 117.96(17) . . ?
C2 C1 C6 120.8(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.1(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.70(19) . . ?
C1 C6 C7 119.16(18) . . ?
C5 C6 C7 122.09(18) . . ?
O1 C7 N1 122.65(19) . . ?
O1 C7 C6 121.43(18) . . ?
N1 C7 C6 115.90(18) . . ?
C9 C8 C13 119.6(2) . . ?
C9 C8 N1 116.87(19) . . ?
C13 C8 N1 123.43(18) . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.7(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 119.3(2) . . ?
C12 C13 N2 121.29(19) . . ?
C8 C13 N2 119.35(18) . . ?
O2 C14 N2 125.6(2) . . ?
O2 C14 C15 121.50(19) . . ?
N2 C14 C15 112.84(17) . . ?
N5 C15 C16 123.1(2) . . ?
N5 C15 C14 116.65(18) . . ?
C16 C15 C14 120.27(19) . . ?
C15 C16 C17 118.4(2) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C18 C17 C16 119.1(2) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 118.5(2) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
N5 C19 C18 122.89(19) . . ?
N5 C19 C20 116.15(18) . . ?
C18 C19 C20 120.95(19) . . ?
O3 C20 N3 124.11(19) . . ?
O3 C20 C19 120.91(19) . . ?
N3 C20 C19 114.97(17) . . ?
C22 C21 C26 119.99(19) . . ?
C22 C21 N3 117.43(18) . . ?
C26 C21 N3 122.46(18) . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 119.5(2) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C23 C24 C25 120.3(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 118.94(19) . . ?
C25 C26 N4 120.83(18) . . ?
C21 C26 N4 120.23(18) . . ?
O4 C27 N4 122.31(19) . . ?
O4 C27 C28 121.14(18) . . ?
N4 C27 C28 116.47(17) . . ?
C30 C28 C29 109.31(19) . . ?
C30 C28 C31 109.13(19) . . ?
C29 C28 C31 109.95(18) . . ?
C30 C28 C27 114.36(17) . . ?
C29 C28 C27 108.08(17) . . ?
C31 C28 C27 105.92(17) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C100 O100 C101 109.24(17) . . ?
O100 C100 C101 110.8(2) . 2_765 ?
O100 C100 H10A 109.5 . . ?
C101 C100 H10A 109.5 2_765 . ?
O100 C100 H10B 109.5 . . ?
C101 C100 H10B 109.5 2_765 . ?
H10A C100 H10B 108.1 . . ?
O100 C101 C100 110.9(2) . 2_765 ?
O100 C101 H10C 109.5 . . ?
C100 C101 H10C 109.5 2_765 . ?
O100 C101 H10D 109.5 . . ?
C100 C101 H10D 109.5 2_765 . ?
H10C C101 H10D 108.1 . . ?

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
C6 C1 C2 C3 -1.0(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C2 C1 C6 C5 2.0(3) . . . . ?
C2 C1 C6 C7 179.5(2) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C5 C6 C7 -178.74(19) . . . . ?
C8 N1 C7 O1 -10.9(3) . . . . ?
C8 N1 C7 C6 170.52(18) . . . . ?
C1 C6 C7 O1 -31.6(3) . . . . ?
C5 C6 C7 O1 145.8(2) . . . . ?
C1 C6 C7 N1 146.98(19) . . . . ?
C5 C6 C7 N1 -35.6(3) . . . . ?
C7 N1 C8 C9 -127.5(2) . . . . ?
C7 N1 C8 C13 55.7(3) . . . . ?
C13 C8 C9 C10 0.5(3) . . . . ?
N1 C8 C9 C10 -176.48(19) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C8 0.6(3) . . . . ?
C11 C12 C13 N2 -176.54(19) . . . . ?
C9 C8 C13 C12 -1.1(3) . . . . ?
N1 C8 C13 C12 175.62(18) . . . . ?
C9 C8 C13 N2 176.07(18) . . . . ?
N1 C8 C13 N2 -7.2(3) . . . . ?
C14 N2 C13 C12 -29.5(3) . . . . ?
C14 N2 C13 C8 153.4(2) . . . . ?
C13 N2 C14 O2 -12.0(3) . . . . ?
C13 N2 C14 C15 169.93(18) . . . . ?
C19 N5 C15 C16 0.1(3) . . . . ?
C19 N5 C15 C14 179.88(17) . . . . ?
O2 C14 C15 N5 174.63(19) . . . . ?
N2 C14 C15 N5 -7.3(3) . . . . ?
O2 C14 C15 C16 -5.6(3) . . . . ?
N2 C14 C15 C16 172.55(18) . . . . ?
N5 C15 C16 C17 1.5(3) . . . . ?
C14 C15 C16 C17 -178.32(19) . . . . ?
C15 C16 C17 C18 -1.9(3) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C15 N5 C19 C18 -1.2(3) . . . . ?
C15 N5 C19 C20 177.77(17) . . . . ?
C17 C18 C19 N5 0.8(3) . . . . ?
C17 C18 C19 C20 -178.19(19) . . . . ?
C21 N3 C20 O3 7.1(3) . . . . ?
C21 N3 C20 C19 -173.00(18) . . . . ?
N5 C19 C20 O3 -173.32(18) . . . . ?
C18 C19 C20 O3 5.7(3) . . . . ?
N5 C19 C20 N3 6.8(3) . . . . ?
C18 C19 C20 N3 -174.19(19) . . . . ?
C20 N3 C21 C22 131.9(2) . . . . ?
C20 N3 C21 C26 -51.9(3) . . . . ?
C26 C21 C22 C23 2.2(3) . . . . ?
N3 C21 C22 C23 178.5(2) . . . . ?
C21 C22 C23 C24 1.7(4) . . . . ?
C22 C23 C24 C25 -2.7(4) . . . . ?
C23 C24 C25 C26 -0.1(4) . . . . ?
C24 C25 C26 C21 4.0(3) . . . . ?
C24 C25 C26 N4 -175.0(2) . . . . ?
C22 C21 C26 C25 -5.0(3) . . . . ?
N3 C21 C26 C25 178.94(18) . . . . ?
C22 C21 C26 N4 174.02(19) . . . . ?
N3 C21 C26 N4 -2.0(3) . . . . ?
C27 N4 C26 C25 46.8(3) . . . . ?
C27 N4 C26 C21 -132.2(2) . . . . ?
C26 N4 C27 O4 -2.5(3) . . . . ?
C26 N4 C27 C28 174.42(18) . . . . ?
O4 C27 C28 C30 -164.9(2) . . . . ?
N4 C27 C28 C30 18.1(3) . . . . ?
O4 C27 C28 C29 -42.9(3) . . . . ?
N4 C27 C28 C29 140.09(19) . . . . ?
O4 C27 C28 C31 74.8(2) . . . . ?
N4 C27 C28 C31 -102.1(2) . . . . ?
C101 O100 C100 C101 -57.6(3) . . . 2_765 ?
C100 O100 C101 C100 57.6(3) . . . 2_765 ?

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 O3 0.92(2) 2.03(2) 2.906(2) 159.5(19) 1_455
N2 H2N O1 0.87(2) 1.95(2) 2.726(2) 148(2) .
N2 H2N N5 0.87(2) 2.19(2) 2.641(2) 111.6(18) .
N3 H3N O1 0.85(2) 2.13(2) 2.911(2) 152(2) .
N3 H3N N5 0.85(2) 2.22(2) 2.662(2) 112.3(18) .
N4 H4N O3 0.87(2) 2.02(2) 2.765(2) 144(2) .

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.047

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# 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-Ac-at
_database_code_depnum_ccdc_archive 'CCDC 1438546'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H25 N5 O4, C3 D6 O'
_chemical_formula_sum            'C36 H25 D6 N5 O5'
_chemical_formula_weight         619.69

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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.8945(3)
_cell_length_b                   19.3946(4)
_cell_length_c                   11.2987(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.960(2)
_cell_angle_gamma                90
_cell_volume                     3040.69(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3663
_cell_measurement_theta_min      3.8950
_cell_measurement_theta_max      75.7470

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.031
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.977
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 13 0 0.0282 1.0000 13.0000 -0.0000 0.2021 0.5475 0.8598
3 -12 0 0.0337 3.0000 -12.0000 0.0000 0.2420 -0.4698 -0.8615
-9 0 0 0.0100 -9.0000 -0.0000 -0.0000 -0.9831 -0.0817 0.1557
-9 -2 0 0.0115 -9.0000 -2.0000 -0.0000 -0.9974 -0.1645 0.0208
9 2 0 0.0197 9.0000 2.0000 0.0000 0.9974 0.1645 -0.0208
9 -3 0 0.0250 9.0000 -3.0000 0.0000 0.9617 -0.0426 -0.3581
-3 12 0 0.0279 -3.0000 12.0000 -0.0000 -0.2420 0.4698 0.8615
4 1 -7 0.1144 4.0000 1.0000 -7.0000 0.2509 0.8845 -0.4761
-4 1 7 0.1082 -4.0000 1.0000 7.0000 -0.2367 -0.8016 0.6111
-1 -13 1 0.0305 -1.0000 -13.0000 1.0000 -0.1745 -0.6627 -0.7920
-4 -1 -7 0.1027 -4.0000 -1.0000 -7.0000 -0.6372 0.7290 -0.4726
3 2 7 0.1178 3.0000 2.0000 7.0000 0.5351 -0.6967 0.5574
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_reflns_number            10310
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.917
_diffrn_reflns_theta_max         76.614
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6088
_reflns_number_gt                4673
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0706P)²+0.8430P] 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         6088
_refine_ls_number_parameters     429
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1617
_refine_ls_wR_factor_gt          0.1478
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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 0.25177(12) 0.37324(8) 0.68896(13) 0.0269(3) Uani 1 1 d . . . . .
O2 O 0.19222(13) 0.37216(8) 0.25199(13) 0.0292(4) Uani 1 1 d . . . . .
O3 O 0.09356(16) 0.61827(9) 0.68740(15) 0.0423(5) Uani 1 1 d . . . . .
O4 O 0.48929(14) 0.55828(10) 0.82372(17) 0.0412(4) Uani 1 1 d . . . . .
N1 N 0.22341(14) 0.26123(10) 0.63858(16) 0.0261(4) Uani 1 1 d . . . . .
H1N H 0.207(2) 0.2206(16) 0.667(3) 0.031 Uiso 1 1 d . U . . .
N2 N 0.23360(15) 0.36236(10) 0.45112(16) 0.0267(4) Uani 1 1 d . . . . .
H2N H 0.229(2) 0.3832(16) 0.512(3) 0.032 Uiso 1 1 d . U . . .
N3 N 0.18402(15) 0.52116(10) 0.71983(17) 0.0274(4) Uani 1 1 d . . . . .
H3N H 0.207(2) 0.4856(16) 0.687(3) 0.033 Uiso 1 1 d . U . . .
N4 N 0.36863(15) 0.47936(10) 0.79971(18) 0.0295(4) Uani 1 1 d . . . . .
H4N H 0.345(2) 0.4458(17) 0.757(3) 0.035 Uiso 1 1 d . U . . .
N5 N 0.15074(14) 0.48094(9) 0.49680(16) 0.0248(4) Uani 1 1 d . . . . .
C1 C 0.14623(17) 0.35819(11) 0.89382(19) 0.0268(4) Uani 1 1 d . . . . .
H1 H 0.1969 0.3911 0.8976 0.032 Uiso 1 1 calc R U . . .
C2 C 0.08089(18) 0.35613(12) 0.9822(2) 0.0307(5) Uani 1 1 d . . . . .
H2 H 0.0872 0.3874 1.0468 0.037 Uiso 1 1 calc R U . . .
C3 C 0.00645(18) 0.30879(12) 0.9768(2) 0.0311(5) Uani 1 1 d . . . . .
H3 H -0.0385 0.3078 1.0374 0.037 Uiso 1 1 calc R U . . .
C4 C -0.00271(18) 0.26251(12) 0.8827(2) 0.0317(5) Uani 1 1 d . . . . .
H4 H -0.0538 0.2299 0.8790 0.038 Uiso 1 1 calc R U . . .
C5 C 0.06309(17) 0.26407(11) 0.7941(2) 0.0285(5) Uani 1 1 d . . . . .
H5 H 0.0570 0.2323 0.7301 0.034 Uiso 1 1 calc R U . . .
C6 C 0.13772(16) 0.31176(11) 0.79876(19) 0.0249(4) Uani 1 1 d . . . . .
C7 C 0.20906(16) 0.31795(11) 0.70512(18) 0.0242(4) Uani 1 1 d . . . . .
C8 C 0.29047(16) 0.25608(11) 0.54721(18) 0.0254(4) Uani 1 1 d . . . . .
C9 C 0.34926(18) 0.19795(11) 0.54730(19) 0.0291(5) Uani 1 1 d . . . . .
H9 H 0.3446 0.1644 0.6081 0.035 Uiso 1 1 calc R U . . .
C10 C 0.41480(19) 0.18818(12) 0.4597(2) 0.0319(5) Uani 1 1 d . . . . .
H10 H 0.4543 0.1482 0.4602 0.038 Uiso 1 1 calc R U . . .
C11 C 0.42180(19) 0.23766(12) 0.3715(2) 0.0324(5) Uani 1 1 d . . . . .
H11 H 0.4675 0.2322 0.3125 0.039 Uiso 1 1 calc R U . . .
C12 C 0.36239(18) 0.29473(12) 0.36962(19) 0.0293(5) Uani 1 1 d . . . . .
H12 H 0.3679 0.3283 0.3090 0.035 Uiso 1 1 calc R U . . .
C13 C 0.29449(17) 0.30412(11) 0.45492(19) 0.0256(4) Uani 1 1 d . . . . .
C14 C 0.19127(16) 0.39324(11) 0.35505(19) 0.0252(4) Uani 1 1 d . . . . .
C15 C 0.14102(16) 0.45965(11) 0.38416(19) 0.0250(4) Uani 1 1 d . . . . .
C16 C 0.09151(17) 0.49759(12) 0.29618(19) 0.0289(5) Uani 1 1 d . . . . .
H16 H 0.0851 0.4809 0.2171 0.035 Uiso 1 1 calc R U . . .
C17 C 0.05170(18) 0.56023(13) 0.3263(2) 0.0318(5) Uani 1 1 d . . . . .
H17 H 0.0172 0.5872 0.2681 0.038 Uiso 1 1 calc R U . . .
C18 C 0.06283(18) 0.58327(12) 0.4427(2) 0.0294(5) Uani 1 1 d . . . . .
H18 H 0.0371 0.6264 0.4653 0.035 Uiso 1 1 calc R U . . .
C19 C 0.11243(16) 0.54163(11) 0.52480(19) 0.0262(4) Uani 1 1 d . . . . .
C20 C 0.12845(17) 0.56477(12) 0.6524(2) 0.0283(5) Uani 1 1 d . . . . .
C21 C 0.21354(17) 0.53062(11) 0.84050(19) 0.0272(5) Uani 1 1 d . . . . .
C22 C 0.15127(19) 0.55959(12) 0.9202(2) 0.0312(5) Uani 1 1 d . . . . .
H22 H 0.0885 0.5740 0.8937 0.037 Uiso 1 1 calc R U . . .
C23 C 0.1819(2) 0.56705(14) 1.0379(2) 0.0381(6) Uani 1 1 d . . . . .
H23 H 0.1401 0.5877 1.0917 0.046 Uiso 1 1 calc R U . . .
C24 C 0.2721(2) 0.54503(15) 1.0785(2) 0.0410(6) Uani 1 1 d . . . . .
H24 H 0.2921 0.5502 1.1597 0.049 Uiso 1 1 calc R U . . .
C25 C 0.3333(2) 0.51531(13) 0.9998(2) 0.0358(5) Uani 1 1 d . . . . .
H25 H 0.3948 0.4989 1.0277 0.043 Uiso 1 1 calc R U . . .
C26 C 0.30513(18) 0.50948(12) 0.8805(2) 0.0290(5) Uani 1 1 d . . . . .
C27 C 0.45650(18) 0.50583(12) 0.7768(2) 0.0302(5) Uani 1 1 d . . . . .
C28 C 0.51025(16) 0.46628(12) 0.6876(2) 0.0294(5) Uani 1 1 d . . . . .
C29 C 0.58089(18) 0.50061(14) 0.6275(2) 0.0375(6) Uani 1 1 d . . . . .
H29 H 0.5962 0.5471 0.6469 0.045 Uiso 1 1 calc R U . . .
C30 C 0.62896(19) 0.46720(16) 0.5396(2) 0.0422(6) Uani 1 1 d . . . . .
H30 H 0.6759 0.4914 0.4976 0.051 Uiso 1 1 calc R U . . .
C31 C 0.6092(2) 0.39922(17) 0.5127(2) 0.0443(6) Uani 1 1 d . . . . .
H31 H 0.6431 0.3765 0.4531 0.053 Uiso 1 1 calc R U . . .
C32 C 0.5397(2) 0.36395(14) 0.5727(2) 0.0396(6) Uani 1 1 d . . . . .
H32 H 0.5263 0.3170 0.5546 0.047 Uiso 1 1 calc R U . . .
C33 C 0.49008(18) 0.39730(13) 0.6591(2) 0.0331(5) Uani 1 1 d . . . . .
H33 H 0.4420 0.3732 0.6993 0.040 Uiso 1 1 calc R U . . .
O100 O 0.7968(2) 0.26442(17) 0.5577(3) 0.0869(10) Uani 1 1 d . . . . .
C100 C 0.7458(2) 0.25214(18) 0.6385(3) 0.0543(8) Uani 1 1 d . . . . .
C101 C 0.7529(3) 0.2939(3) 0.7475(4) 0.0806(13) Uani 1 1 d . . . . .
D10A D 0.8072 0.3259 0.7440 0.121 Uiso 1 1 calc R U . . .
D10B D 0.7631 0.2635 0.8163 0.121 Uiso 1 1 calc R U . . .
D10C D 0.6931 0.3200 0.7548 0.121 Uiso 1 1 calc R U . . .
C102 C 0.6732(3) 0.1967(2) 0.6324(6) 0.0961(18) Uani 1 1 d . . . . .
D10D D 0.6707 0.1760 0.5532 0.144 Uiso 1 1 calc R U . . .
D10E D 0.6099 0.2159 0.6483 0.144 Uiso 1 1 calc R U . . .
D10F D 0.6907 0.1614 0.6916 0.144 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 C7 1.243(3) . ?
O2 C14 1.235(3) . ?
O3 C20 1.220(3) . ?
O4 C27 1.224(3) . ?
N1 C7 1.353(3) . ?
N1 C8 1.429(3) . ?
N1 H1N 0.88(3) . ?
N2 C14 1.348(3) . ?
N2 C13 1.410(3) . ?
N2 H2N 0.80(3) . ?
N3 C20 1.353(3) . ?
N3 C21 1.415(3) . ?
N3 H3N 0.85(3) . ?
N4 C27 1.362(3) . ?
N4 C26 1.427(3) . ?
N4 H4N 0.86(3) . ?
N5 C19 1.336(3) . ?
N5 C15 1.338(3) . ?
C1 C2 1.384(3) . ?
C1 C6 1.402(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.492(3) . ?
C8 C9 1.392(3) . ?
C8 C13 1.402(3) . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.509(3) . ?
C15 C16 1.390(3) . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.516(3) . ?
C21 C26 1.390(3) . ?
C21 C22 1.398(3) . ?
C22 C23 1.383(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(3) . ?
C25 H25 0.9500 . ?
C27 C28 1.497(3) . ?
C28 C29 1.391(3) . ?
C28 C33 1.401(3) . ?
C29 C30 1.386(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.377(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.388(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.384(4) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
O100 C100 1.209(4) . ?
C100 C102 1.473(5) . ?
C100 C101 1.473(5) . ?
C101 D10A 0.9800 . ?
C101 D10B 0.9800 . ?
C101 D10C 0.9800 . ?
C102 D10D 0.9800 . ?
C102 D10E 0.9800 . ?
C102 D10F 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
C7 N1 C8 125.33(19) . . ?
C7 N1 H1N 118.3(19) . . ?
C8 N1 H1N 112.8(18) . . ?
C14 N2 C13 128.06(19) . . ?
C14 N2 H2N 114(2) . . ?
C13 N2 H2N 117(2) . . ?
C20 N3 C21 126.13(19) . . ?
C20 N3 H3N 119(2) . . ?
C21 N3 H3N 115(2) . . ?
C27 N4 C26 123.9(2) . . ?
C27 N4 H4N 120(2) . . ?
C26 N4 H4N 116(2) . . ?
C19 N5 C15 118.36(19) . . ?
C2 C1 C6 120.1(2) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 C7 123.3(2) . . ?
C1 C6 C7 117.3(2) . . ?
O1 C7 N1 122.30(19) . . ?
O1 C7 C6 120.88(19) . . ?
N1 C7 C6 116.81(19) . . ?
C9 C8 C13 119.5(2) . . ?
C9 C8 N1 117.41(19) . . ?
C13 C8 N1 122.9(2) . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 118.8(2) . . ?
C12 C13 N2 120.6(2) . . ?
C8 C13 N2 120.5(2) . . ?
O2 C14 N2 125.9(2) . . ?
O2 C14 C15 121.0(2) . . ?
N2 C14 C15 113.03(18) . . ?
N5 C15 C16 122.6(2) . . ?
N5 C15 C14 116.46(19) . . ?
C16 C15 C14 120.88(19) . . ?
C17 C16 C15 118.5(2) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 119.2(2) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 118.2(2) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
N5 C19 C18 123.0(2) . . ?
N5 C19 C20 116.4(2) . . ?
C18 C19 C20 120.5(2) . . ?
O3 C20 N3 125.1(2) . . ?
O3 C20 C19 121.3(2) . . ?
N3 C20 C19 113.70(19) . . ?
C26 C21 C22 119.7(2) . . ?
C26 C21 N3 119.3(2) . . ?
C22 C21 N3 121.0(2) . . ?
C23 C22 C21 119.4(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 119.4(2) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C26 120.3(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 119.9(2) . . ?
C25 C26 N4 120.1(2) . . ?
C21 C26 N4 119.9(2) . . ?
O4 C27 N4 123.3(2) . . ?
O4 C27 C28 122.0(2) . . ?
N4 C27 C28 114.7(2) . . ?
C29 C28 C33 118.8(2) . . ?
C29 C28 C27 118.2(2) . . ?
C33 C28 C27 122.9(2) . . ?
C30 C29 C28 120.3(3) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C31 C30 C29 120.5(3) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 120.0(3) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C33 C32 C31 119.9(3) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C28 120.5(2) . . ?
C32 C33 H33 119.7 . . ?
C28 C33 H33 119.7 . . ?
O100 C100 C102 122.4(4) . . ?
O100 C100 C101 120.4(4) . . ?
C102 C100 C101 117.2(4) . . ?
C100 C101 D10A 109.5 . . ?
C100 C101 D10B 109.5 . . ?
D10A C101 D10B 109.5 . . ?
C100 C101 D10C 109.5 . . ?
D10A C101 D10C 109.5 . . ?
D10B C101 D10C 109.5 . . ?
C100 C102 D10D 109.5 . . ?
C100 C102 D10E 109.5 . . ?
D10D C102 D10E 109.5 . . ?
C100 C102 D10F 109.5 . . ?
D10D C102 D10F 109.5 . . ?
D10E C102 D10F 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
C6 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 -178.0(2) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C2 C1 C6 C7 178.5(2) . . . . ?
C8 N1 C7 O1 2.9(4) . . . . ?
C8 N1 C7 C6 -178.1(2) . . . . ?
C5 C6 C7 O1 154.6(2) . . . . ?
C1 C6 C7 O1 -23.6(3) . . . . ?
C5 C6 C7 N1 -24.4(3) . . . . ?
C1 C6 C7 N1 157.4(2) . . . . ?
C7 N1 C8 C9 133.1(2) . . . . ?
C7 N1 C8 C13 -51.3(3) . . . . ?
C13 C8 C9 C10 2.6(3) . . . . ?
N1 C8 C9 C10 178.4(2) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C10 C11 C12 -1.7(4) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C8 3.2(3) . . . . ?
C11 C12 C13 N2 -179.3(2) . . . . ?
C9 C8 C13 C12 -4.4(3) . . . . ?
N1 C8 C13 C12 -179.9(2) . . . . ?
C9 C8 C13 N2 178.1(2) . . . . ?
N1 C8 C13 N2 2.6(3) . . . . ?
C14 N2 C13 C12 38.6(3) . . . . ?
C14 N2 C13 C8 -144.0(2) . . . . ?
C13 N2 C14 O2 6.4(4) . . . . ?
C13 N2 C14 C15 -172.8(2) . . . . ?
C19 N5 C15 C16 -1.1(3) . . . . ?
C19 N5 C15 C14 175.92(19) . . . . ?
O2 C14 C15 N5 -174.7(2) . . . . ?
N2 C14 C15 N5 4.5(3) . . . . ?
O2 C14 C15 C16 2.3(3) . . . . ?
N2 C14 C15 C16 -178.5(2) . . . . ?
N5 C15 C16 C17 0.8(3) . . . . ?
C14 C15 C16 C17 -176.1(2) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C17 C18 C19 -1.1(4) . . . . ?
C15 N5 C19 C18 0.3(3) . . . . ?
C15 N5 C19 C20 -177.82(19) . . . . ?
C17 C18 C19 N5 0.8(4) . . . . ?
C17 C18 C19 C20 178.8(2) . . . . ?
C21 N3 C20 O3 -1.9(4) . . . . ?
C21 N3 C20 C19 177.7(2) . . . . ?
N5 C19 C20 O3 -177.5(2) . . . . ?
C18 C19 C20 O3 4.3(4) . . . . ?
N5 C19 C20 N3 2.8(3) . . . . ?
C18 C19 C20 N3 -175.3(2) . . . . ?
C20 N3 C21 C26 -143.3(2) . . . . ?
C20 N3 C21 C22 38.0(3) . . . . ?
C26 C21 C22 C23 0.2(4) . . . . ?
N3 C21 C22 C23 178.9(2) . . . . ?
C21 C22 C23 C24 -1.4(4) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C23 C24 C25 C26 1.8(4) . . . . ?
C24 C25 C26 C21 -2.9(4) . . . . ?
C24 C25 C26 N4 179.5(2) . . . . ?
C22 C21 C26 C25 1.9(3) . . . . ?
N3 C21 C26 C25 -176.8(2) . . . . ?
C22 C21 C26 N4 179.5(2) . . . . ?
N3 C21 C26 N4 0.8(3) . . . . ?
C27 N4 C26 C25 -62.1(3) . . . . ?
C27 N4 C26 C21 120.4(3) . . . . ?
C26 N4 C27 O4 -0.1(4) . . . . ?
C26 N4 C27 C28 -179.2(2) . . . . ?
O4 C27 C28 C29 -22.0(3) . . . . ?
N4 C27 C28 C29 157.1(2) . . . . ?
O4 C27 C28 C33 160.4(2) . . . . ?
N4 C27 C28 C33 -20.5(3) . . . . ?
C33 C28 C29 C30 1.1(4) . . . . ?
C27 C28 C29 C30 -176.5(2) . . . . ?
C28 C29 C30 C31 -1.6(4) . . . . ?
C29 C30 C31 C32 0.9(4) . . . . ?
C30 C31 C32 C33 0.4(4) . . . . ?
C31 C32 C33 C28 -0.8(4) . . . . ?
C29 C28 C33 C32 0.1(4) . . . . ?
C27 C28 C33 C32 177.7(2) . . . . ?

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 O2 0.88(3) 2.05(3) 2.929(2) 170(3) 4_566
N2 H2N O1 0.80(3) 2.02(3) 2.694(2) 142(3) .
N2 H2N N5 0.80(3) 2.19(3) 2.635(3) 116(3) .
N3 H3N O1 0.85(3) 2.27(3) 3.045(2) 152(3) .
N4 H4N O1 0.86(3) 2.04(3) 2.868(3) 161(3) .

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.059

_shelxl_version_number           2014/6

