# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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#######################################################################

data_jsn29
_database_code_depnum_ccdc_archive 'CCDC 1523518'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        Acetyl-DELTA1-5-Arg10-teixobactin
_chemical_name_common            Ac-DELTA1-5-Arg10-teixobactin
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H57 Cl N9 O10.50'
_chemical_formula_weight         747.29

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   19.376(3)
_cell_length_b                   12.405(2)
_cell_length_c                   16.135(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.809(3)
_cell_angle_gamma                90
_cell_volume                     3864.5(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    88(2)
_cell_measurement_reflns_used    5818
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      25.52

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    not_measured
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             1604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8121
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      88(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21510
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.951
_diffrn_reflns_theta_max         26.393
_diffrn_reflns_theta_full        25.500
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7914
_reflns_number_gt                6389
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2 2014.11-0, 2014'
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
A colorless crystal of approximate dimensions 0.030 x 0.130 x 0.200 mm was 
mounted in a cryoloop and transferred to a Bruker SMART APEX II diffractometer.  
The APEX2 program package was used to determine the unit-cell parameters and 
for data collection (180 sec/frame scan time for a sphere of diffraction data).  
The raw frame data was processed using SAINT and SADABS to yield the reflection 
data file.  Subsequent calculations were carried out using the SHELXTL program.  
The diffraction symmetry was 2/m and the systematic absences were consistent 
with the monoclinic space groups C2, Cm and C2/m.  It was later determined that 
space group C2 was correct.

The structure was solved by direct methods and refined on F2 by full-matrix 
least-squares techniques.  The analytical scattering factors for neutral atoms 
were used throughout the analysis.  Hydrogen atoms were either located from a 
difference-Fourier map and refined (x,y,z and Uiso) or were included using a 
riding model.  There were 1.5 molecules of water solvent present per formula-unit.  
One water molecule was located on a two fold rotation axis.  Water hydrogen atoms 
were refined with d(O-H) = 0.85Å.

At convergence, wR2 = 0.0878 and Goof = 1.016 for 520 variables refined against 7914 
data (0.80Å), R1 = 0.0424 for those 6389 data with I > 2.0sigma(I).  The absolute 
structure was assigned by refinement of the Flack parameter.

There was a single residual (1.23e-) present in the final difference-Fourier map.  It 
was not possible to determine the nature of the residual.  The SQUEEZE routine in the 
PLATON program package was used to account for the electrons associated with the 
solvent accessible voids.  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2501 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7914
_refine_ls_number_parameters     520
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.005
_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
Cl1 Cl 0.56654(4) 0.52652(6) 0.21884(6) 0.0192(2) Uani 1 1 d . . . . .
O1 O 0.80522(14) 0.7259(2) 0.42105(17) 0.0360(8) Uani 1 1 d . . . . .
O2 O 0.74654(12) 0.60846(19) 0.33510(14) 0.0181(6) Uani 1 1 d . . . . .
O3 O 0.76799(12) 0.77863(19) 0.19585(16) 0.0212(6) Uani 1 1 d . . . . .
O4 O 0.62869(13) 0.94208(19) 0.16568(16) 0.0244(6) Uani 1 1 d . . . . .
O5 O 0.61548(15) 0.8877(2) 0.41114(18) 0.0371(8) Uani 1 1 d . . . . .
O6 O 0.81274(11) 0.42747(19) 0.08699(15) 0.0183(6) Uani 1 1 d . . . . .
O7 O 0.63100(14) 0.48762(19) 0.01560(16) 0.0205(6) Uani 1 1 d . . . . .
H7A H 0.588(2) 0.479(3) 0.016(3) 0.036(13) Uiso 1 1 d . . . . .
O8 O 0.71166(12) 0.1978(2) 0.21313(17) 0.0259(6) Uani 1 1 d . . . . .
O9 O 0.47773(13) 0.24789(19) 0.13168(16) 0.0226(6) Uani 1 1 d . . . . .
N1 N 0.63037(15) 0.7133(3) 0.3751(2) 0.0180(7) Uani 1 1 d . . . . .
H1 H 0.622(2) 0.662(3) 0.342(2) 0.027(12) Uiso 1 1 d . . . . .
N2 N 0.68851(15) 0.6844(3) 0.11689(18) 0.0152(7) Uani 1 1 d . . . . .
H2 H 0.6722(19) 0.630(3) 0.105(2) 0.014(11) Uiso 1 1 d . . . . .
N3 N 0.58894(15) 0.7826(2) 0.21138(18) 0.0160(7) Uani 1 1 d . . . . .
H3 H 0.5882(19) 0.707(3) 0.203(2) 0.024(10) Uiso 1 1 d . . . . .
N4 N 0.73973(15) 0.4926(2) 0.17745(18) 0.0140(6) Uani 1 1 d . . . . .
H4 H 0.699(2) 0.493(3) 0.194(2) 0.027(11) Uiso 1 1 d . . . . .
N5 N 0.64854(16) 0.3236(2) 0.13980(19) 0.0160(7) Uani 1 1 d . . . . .
H5 H 0.618(2) 0.360(3) 0.142(2) 0.023(12) Uiso 1 1 d . . . . .
N6 N 0.55666(15) 0.1386(2) 0.20064(19) 0.0160(7) Uani 1 1 d . . . . .
H6 H 0.5740(17) 0.075(3) 0.200(2) 0.009(9) Uiso 1 1 d . . . . .
N7 N 0.40188(16) 0.5893(2) 0.20867(18) 0.0170(7) Uani 1 1 d . . . . .
H7 H 0.446(2) 0.582(3) 0.208(2) 0.024(11) Uiso 1 1 d . . . . .
N8 N 0.39188(19) 0.4057(3) 0.2052(2) 0.0197(7) Uani 1 1 d . . . . .
H8A H 0.432(2) 0.403(4) 0.202(3) 0.036(14) Uiso 1 1 d . . . . .
H8B H 0.3663(18) 0.350(3) 0.205(2) 0.010(9) Uiso 1 1 d . . . . .
N9 N 0.29458(15) 0.5089(3) 0.2121(2) 0.0194(7) Uani 1 1 d . . . . .
H9A H 0.269(2) 0.573(4) 0.206(2) 0.032(12) Uiso 1 1 d . . . . .
H9B H 0.2726(18) 0.447(3) 0.209(2) 0.017(10) Uiso 1 1 d . . . . .
C1 C 0.5771(2) 0.5011(3) 0.5730(2) 0.0321(10) Uani 1 1 d . . . . .
H1A H 0.5662 0.4482 0.5287 0.048 Uiso 1 1 calc R U . . .
H1B H 0.5351 0.5180 0.6002 0.048 Uiso 1 1 calc R U . . .
H1C H 0.6121 0.4711 0.6140 0.048 Uiso 1 1 calc R U . . .
C2 C 0.60501(19) 0.6036(3) 0.5358(2) 0.0241(9) Uani 1 1 d . . . . .
H2A H 0.6176 0.6553 0.5812 0.029 Uiso 1 1 calc R U . . .
H2B H 0.5679 0.6367 0.4983 0.029 Uiso 1 1 calc R U . . .
C3 C 0.66808(18) 0.5843(3) 0.4871(2) 0.0213(8) Uani 1 1 d . . . . .
H3A H 0.6564 0.5260 0.4455 0.026 Uiso 1 1 calc R U . . .
C4 C 0.7312(2) 0.5476(4) 0.5444(3) 0.0357(11) Uani 1 1 d . . . . .
H4A H 0.7714 0.5399 0.5118 0.054 Uiso 1 1 calc R U . . .
H4B H 0.7211 0.4782 0.5697 0.054 Uiso 1 1 calc R U . . .
H4C H 0.7414 0.6014 0.5883 0.054 Uiso 1 1 calc R U . . .
C5 C 0.68517(17) 0.6874(3) 0.4397(2) 0.0183(8) Uani 1 1 d . . . . .
H5A H 0.6890 0.7485 0.4803 0.022 Uiso 1 1 calc R U . . .
C6 C 0.75312(19) 0.6788(3) 0.4000(2) 0.0215(9) Uani 1 1 d . . . . .
C7 C 0.80783(17) 0.5943(3) 0.2898(2) 0.0175(8) Uani 1 1 d . . . . .
H7B H 0.8378 0.6596 0.2982 0.021 Uiso 1 1 calc R U . . .
C8 C 0.84781(19) 0.4976(3) 0.3232(2) 0.0265(9) Uani 1 1 d . . . . .
H8C H 0.8591 0.5061 0.3832 0.040 Uiso 1 1 calc R U . . .
H8D H 0.8907 0.4910 0.2954 0.040 Uiso 1 1 calc R U . . .
H8E H 0.8197 0.4325 0.3128 0.040 Uiso 1 1 calc R U . . .
C9 C 0.78153(17) 0.5871(3) 0.1985(2) 0.0149(7) Uani 1 1 d . . . . .
H9 H 0.8234 0.5813 0.1666 0.018 Uiso 1 1 calc R U . . .
C10 C 0.74479(16) 0.6912(3) 0.1698(2) 0.0141(7) Uani 1 1 d . . . . .
C11 C 0.65247(18) 0.7830(3) 0.0879(2) 0.0176(8) Uani 1 1 d . . . . .
H11 H 0.6865 0.8310 0.0628 0.021 Uiso 1 1 calc R U . . .
C12 C 0.59489(19) 0.7551(3) 0.0207(2) 0.0225(9) Uani 1 1 d . . . . .
H12A H 0.6151 0.7215 -0.0267 0.034 Uiso 1 1 calc R U . . .
H12B H 0.5704 0.8210 0.0022 0.034 Uiso 1 1 calc R U . . .
H12C H 0.5623 0.7049 0.0434 0.034 Uiso 1 1 calc R U . . .
C13 C 0.62318(17) 0.8436(3) 0.1597(2) 0.0154(8) Uani 1 1 d . . . . .
C14 C 0.55623(17) 0.8261(3) 0.2828(2) 0.0154(8) Uani 1 1 d . . . . .
H14 H 0.5475 0.9047 0.2731 0.019 Uiso 1 1 calc R U . . .
C15 C 0.60413(18) 0.8132(3) 0.3629(2) 0.0185(8) Uani 1 1 d . . . . .
C16 C 0.75685(17) 0.4234(3) 0.1176(2) 0.0144(7) Uani 1 1 d . . . . .
C17 C 0.70126(17) 0.3459(3) 0.0839(2) 0.0160(8) Uani 1 1 d . . . . .
H17 H 0.7242 0.2761 0.0718 0.019 Uiso 1 1 calc R U . . .
C18 C 0.66815(18) 0.3905(3) 0.0017(2) 0.0199(8) Uani 1 1 d . . . . .
H18A H 0.7046 0.4053 -0.0362 0.024 Uiso 1 1 calc R U . . .
H18B H 0.6361 0.3362 -0.0250 0.024 Uiso 1 1 calc R U . . .
C19 C 0.65719(18) 0.2486(3) 0.2002(2) 0.0166(8) Uani 1 1 d . . . . .
C20 C 0.59383(18) 0.2255(3) 0.2465(2) 0.0166(8) Uani 1 1 d . . . . .
H20 H 0.5637 0.2911 0.2438 0.020 Uiso 1 1 calc R U . . .
C21 C 0.61247(19) 0.1973(3) 0.3378(2) 0.0234(8) Uani 1 1 d . . . . .
H21 H 0.6478 0.1384 0.3399 0.028 Uiso 1 1 calc R U . . .
C22 C 0.6466(2) 0.2970(3) 0.3807(3) 0.0327(10) Uani 1 1 d . . . . .
H22A H 0.6892 0.3147 0.3549 0.049 Uiso 1 1 calc R U . . .
H22B H 0.6576 0.2817 0.4399 0.049 Uiso 1 1 calc R U . . .
H22C H 0.6146 0.3582 0.3746 0.049 Uiso 1 1 calc R U . . .
C23 C 0.5504(2) 0.1568(3) 0.3818(2) 0.0269(9) Uani 1 1 d . . . . .
H23A H 0.5348 0.0875 0.3562 0.032 Uiso 1 1 calc R U . . .
H23B H 0.5661 0.1422 0.4407 0.032 Uiso 1 1 calc R U . . .
C24 C 0.4890(2) 0.2330(3) 0.3790(3) 0.0348(10) Uani 1 1 d . . . . .
H24A H 0.4530 0.2023 0.4112 0.052 Uiso 1 1 calc R U . . .
H24B H 0.4704 0.2433 0.3212 0.052 Uiso 1 1 calc R U . . .
H24C H 0.5039 0.3026 0.4030 0.052 Uiso 1 1 calc R U . . .
C25 C 0.50256(17) 0.1568(3) 0.1448(2) 0.0168(8) Uani 1 1 d . . . . .
C26 C 0.47114(19) 0.0584(3) 0.1017(3) 0.0244(9) Uani 1 1 d . . . . .
H26A H 0.4367 0.0268 0.1357 0.037 Uiso 1 1 calc R U . . .
H26B H 0.5076 0.0055 0.0940 0.037 Uiso 1 1 calc R U . . .
H26C H 0.4487 0.0791 0.0473 0.037 Uiso 1 1 calc R U . . .
C27 C 0.48639(17) 0.7703(3) 0.2915(2) 0.0163(8) Uani 1 1 d . . . . .
H27A H 0.4948 0.6934 0.3056 0.020 Uiso 1 1 calc R U . . .
H27B H 0.4641 0.8038 0.3381 0.020 Uiso 1 1 calc R U . . .
C28 C 0.43683(17) 0.7772(3) 0.2126(2) 0.0167(8) Uani 1 1 d . . . . .
H28A H 0.4190 0.8518 0.2064 0.020 Uiso 1 1 calc R U . . .
H28B H 0.4628 0.7609 0.1638 0.020 Uiso 1 1 calc R U . . .
C29 C 0.37628(18) 0.7003(3) 0.2136(2) 0.0177(8) Uani 1 1 d . . . . .
H29A H 0.3530 0.7100 0.2654 0.021 Uiso 1 1 calc R U . . .
H29B H 0.3422 0.7153 0.1658 0.021 Uiso 1 1 calc R U . . .
C30 C 0.36253(16) 0.5017(3) 0.2089(2) 0.0155(8) Uani 1 1 d . . . . .
O10 O 0.8252(2) 0.5921(3) -0.0353(2) 0.0566(9) Uani 1 1 d D . . . .
H101 H 0.829(3) 0.561(4) -0.0816(18) 0.085 Uiso 1 1 d D U . . .
H102 H 0.827(3) 0.549(4) 0.006(2) 0.085 Uiso 1 1 d D U . . .
O11 O 0.5000 0.3883(3) 0.0000 0.0234(8) Uani 1 2 d DS T P . .
H111 H 0.506(2) 0.343(2) -0.0386(17) 0.035 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 C6 1.192(4) . ?
O2 C6 1.360(4) . ?
O2 C7 1.456(4) . ?
O3 C10 1.235(4) . ?
O4 C13 1.229(4) . ?
O5 C15 1.217(4) . ?
O6 C16 1.228(4) . ?
O7 C18 1.431(4) . ?
O8 C19 1.232(4) . ?
O9 C25 1.240(4) . ?
N1 C15 1.348(5) . ?
N1 C5 1.460(5) . ?
N2 C10 1.330(4) . ?
N2 C11 1.466(4) . ?
N3 C13 1.343(4) . ?
N3 C14 1.464(4) . ?
N4 C16 1.354(4) . ?
N4 C9 1.450(4) . ?
N5 C19 1.347(5) . ?
N5 C17 1.445(4) . ?
N6 C25 1.343(4) . ?
N6 C20 1.462(5) . ?
N7 C30 1.328(4) . ?
N7 C29 1.467(4) . ?
N8 C30 1.324(4) . ?
N9 C30 1.325(4) . ?
C1 C2 1.524(5) . ?
C2 C3 1.526(5) . ?
C3 C4 1.539(5) . ?
C3 C5 1.540(5) . ?
C5 C6 1.516(5) . ?
C7 C8 1.503(5) . ?
C7 C9 1.521(5) . ?
C9 C10 1.527(5) . ?
C11 C13 1.529(5) . ?
C11 C12 1.530(5) . ?
C14 C15 1.534(5) . ?
C14 C27 1.537(5) . ?
C16 C17 1.511(5) . ?
C17 C18 1.527(5) . ?
C19 C20 1.516(5) . ?
C20 C21 1.528(5) . ?
C21 C23 1.531(5) . ?
C21 C22 1.539(5) . ?
C23 C24 1.518(5) . ?
C25 C26 1.507(5) . ?
C27 C28 1.531(5) . ?
C28 C29 1.513(5) . ?

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
C6 O2 C7 115.9(3) . . ?
C15 N1 C5 123.3(3) . . ?
C10 N2 C11 119.7(3) . . ?
C13 N3 C14 123.4(3) . . ?
C16 N4 C9 121.0(3) . . ?
C19 N5 C17 122.2(3) . . ?
C25 N6 C20 122.6(3) . . ?
C30 N7 C29 124.8(3) . . ?
C1 C2 C3 113.5(3) . . ?
C2 C3 C4 111.6(3) . . ?
C2 C3 C5 109.9(3) . . ?
C4 C3 C5 110.5(3) . . ?
N1 C5 C6 108.6(3) . . ?
N1 C5 C3 111.3(3) . . ?
C6 C5 C3 112.4(3) . . ?
O1 C6 O2 123.9(3) . . ?
O1 C6 C5 126.1(3) . . ?
O2 C6 C5 110.0(3) . . ?
O2 C7 C8 109.5(3) . . ?
O2 C7 C9 105.8(3) . . ?
C8 C7 C9 115.0(3) . . ?
N4 C9 C7 114.2(3) . . ?
N4 C9 C10 112.1(3) . . ?
C7 C9 C10 110.7(3) . . ?
O3 C10 N2 122.0(3) . . ?
O3 C10 C9 119.5(3) . . ?
N2 C10 C9 118.5(3) . . ?
N2 C11 C13 111.5(3) . . ?
N2 C11 C12 109.7(3) . . ?
C13 C11 C12 110.7(3) . . ?
O4 C13 N3 123.7(3) . . ?
O4 C13 C11 120.9(3) . . ?
N3 C13 C11 115.3(3) . . ?
N3 C14 C15 110.7(3) . . ?
N3 C14 C27 110.4(3) . . ?
C15 C14 C27 110.6(3) . . ?
O5 C15 N1 124.0(4) . . ?
O5 C15 C14 121.6(3) . . ?
N1 C15 C14 114.4(3) . . ?
O6 C16 N4 122.5(3) . . ?
O6 C16 C17 120.5(3) . . ?
N4 C16 C17 116.8(3) . . ?
N5 C17 C16 114.6(3) . . ?
N5 C17 C18 110.1(3) . . ?
C16 C17 C18 108.5(3) . . ?
O7 C18 C17 110.5(3) . . ?
O8 C19 N5 121.9(3) . . ?
O8 C19 C20 122.5(3) . . ?
N5 C19 C20 115.4(3) . . ?
N6 C20 C19 106.0(3) . . ?
N6 C20 C21 112.7(3) . . ?
C19 C20 C21 112.5(3) . . ?
C20 C21 C23 113.0(3) . . ?
C20 C21 C22 107.9(3) . . ?
C23 C21 C22 112.3(3) . . ?
C24 C23 C21 115.2(3) . . ?
O9 C25 N6 122.5(3) . . ?
O9 C25 C26 121.6(3) . . ?
N6 C25 C26 115.9(3) . . ?
C28 C27 C14 113.2(3) . . ?
C29 C28 C27 112.9(3) . . ?
N7 C29 C28 108.9(3) . . ?
N8 C30 N9 119.6(3) . . ?
N8 C30 N7 119.2(3) . . ?
N9 C30 N7 121.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -66.6(4) . . . . ?
C1 C2 C3 C5 170.4(3) . . . . ?
C15 N1 C5 C6 -101.5(4) . . . . ?
C15 N1 C5 C3 134.2(3) . . . . ?
C2 C3 C5 N1 -66.0(4) . . . . ?
C4 C3 C5 N1 170.4(3) . . . . ?
C2 C3 C5 C6 171.9(3) . . . . ?
C4 C3 C5 C6 48.3(4) . . . . ?
C7 O2 C6 O1 -1.2(5) . . . . ?
C7 O2 C6 C5 178.6(3) . . . . ?
N1 C5 C6 O1 126.6(4) . . . . ?
C3 C5 C6 O1 -109.8(4) . . . . ?
N1 C5 C6 O2 -53.2(4) . . . . ?
C3 C5 C6 O2 70.4(4) . . . . ?
C6 O2 C7 C8 95.3(4) . . . . ?
C6 O2 C7 C9 -140.3(3) . . . . ?
C16 N4 C9 C7 -123.8(3) . . . . ?
C16 N4 C9 C10 109.3(3) . . . . ?
O2 C7 C9 N4 -65.9(3) . . . . ?
C8 C7 C9 N4 55.1(4) . . . . ?
O2 C7 C9 C10 61.8(3) . . . . ?
C8 C7 C9 C10 -177.3(3) . . . . ?
C11 N2 C10 O3 0.1(5) . . . . ?
C11 N2 C10 C9 -179.6(3) . . . . ?
N4 C9 C10 O3 167.1(3) . . . . ?
C7 C9 C10 O3 38.3(4) . . . . ?
N4 C9 C10 N2 -13.1(4) . . . . ?
C7 C9 C10 N2 -141.9(3) . . . . ?
C10 N2 C11 C13 -63.4(4) . . . . ?
C10 N2 C11 C12 173.6(3) . . . . ?
C14 N3 C13 O4 -2.2(5) . . . . ?
C14 N3 C13 C11 -178.9(3) . . . . ?
N2 C11 C13 O4 136.6(3) . . . . ?
C12 C11 C13 O4 -101.0(4) . . . . ?
N2 C11 C13 N3 -46.6(4) . . . . ?
C12 C11 C13 N3 75.8(4) . . . . ?
C13 N3 C14 C15 -96.7(4) . . . . ?
C13 N3 C14 C27 140.5(3) . . . . ?
C5 N1 C15 O5 -11.5(6) . . . . ?
C5 N1 C15 C14 170.0(3) . . . . ?
N3 C14 C15 O5 131.8(4) . . . . ?
C27 C14 C15 O5 -105.5(4) . . . . ?
N3 C14 C15 N1 -49.6(4) . . . . ?
C27 C14 C15 N1 73.1(4) . . . . ?
C9 N4 C16 O6 10.9(5) . . . . ?
C9 N4 C16 C17 -163.8(3) . . . . ?
C19 N5 C17 C16 -83.7(4) . . . . ?
C19 N5 C17 C18 153.7(3) . . . . ?
O6 C16 C17 N5 161.0(3) . . . . ?
N4 C16 C17 N5 -24.2(4) . . . . ?
O6 C16 C17 C18 -75.5(4) . . . . ?
N4 C16 C17 C18 99.3(3) . . . . ?
N5 C17 C18 O7 59.4(4) . . . . ?
C16 C17 C18 O7 -66.8(3) . . . . ?
C17 N5 C19 O8 2.9(5) . . . . ?
C17 N5 C19 C20 -172.8(3) . . . . ?
C25 N6 C20 C19 -97.7(4) . . . . ?
C25 N6 C20 C21 139.0(3) . . . . ?
O8 C19 C20 N6 -85.7(4) . . . . ?
N5 C19 C20 N6 90.0(3) . . . . ?
O8 C19 C20 C21 37.8(4) . . . . ?
N5 C19 C20 C21 -146.6(3) . . . . ?
N6 C20 C21 C23 -51.3(4) . . . . ?
C19 C20 C21 C23 -171.0(3) . . . . ?
N6 C20 C21 C22 -176.1(3) . . . . ?
C19 C20 C21 C22 64.2(4) . . . . ?
C20 C21 C23 C24 -56.6(4) . . . . ?
C22 C21 C23 C24 65.8(4) . . . . ?
C20 N6 C25 O9 -4.4(5) . . . . ?
C20 N6 C25 C26 178.7(3) . . . . ?
N3 C14 C27 C28 -55.4(4) . . . . ?
C15 C14 C27 C28 -178.3(3) . . . . ?
C14 C27 C28 C29 165.8(3) . . . . ?
C30 N7 C29 C28 179.3(3) . . . . ?
C27 C28 C29 N7 -68.1(4) . . . . ?
C29 N7 C30 N8 -179.2(3) . . . . ?
C29 N7 C30 N9 1.4(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
O7 H7A O11 0.84(4) 2.04(4) 2.814(3) 153(4) .
N1 H1 Cl1 0.83(4) 2.76(4) 3.568(3) 166(4) .
N2 H2 O7 0.76(4) 2.38(4) 3.093(4) 158(4) .
N2 H2 N4 0.76(4) 2.40(4) 2.728(4) 108(3) .
N3 H3 Cl1 0.95(4) 2.30(4) 3.210(3) 162(3) .
N4 H4 Cl1 0.85(4) 2.67(4) 3.502(3) 167(3) .
N5 H5 Cl1 0.75(4) 2.64(4) 3.291(3) 145(4) .
N6 H6 O4 0.86(3) 2.06(4) 2.888(4) 161(3) 1_545
N7 H7 Cl1 0.85(4) 2.43(4) 3.275(3) 169(3) .
N8 H8A O9 0.79(5) 2.44(5) 2.887(4) 117(4) .
N8 H8B O3 0.85(4) 2.09(4) 2.865(5) 150(3) 3_445
N9 H9A O8 0.94(4) 1.92(4) 2.841(4) 169(3) 3_455
N9 H9B O3 0.88(4) 2.10(4) 2.911(4) 153(3) 3_445
C17 H17 O10 1.00 2.53 3.274(5) 131.4 4_645
C20 H20 Cl1 1.00 2.95 3.792(4) 142.6 .
C26 H26B O4 0.98 2.65 3.455(4) 140.0 1_545
C26 H26C O10 0.98 2.64 3.465(5) 141.5 3_445
C27 H27A Cl1 0.99 2.92 3.638(4) 130.5 .
O10 H101 O4 0.851(3) 2.21(3) 3.001(4) 155(6) 4_645
O10 H102 O6 0.852(3) 2.029(15) 2.864(4) 166(6) .
O11 H111 O9 0.850(3) 1.960(6) 2.808(3) 176(4) 2_655

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.048




_exptl_crystal_recrystallization_method 'Hanging drop vapor diffusion'
