#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/43/2104325.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2104325
loop_
_publ_author_name
'Ivashevskaya, Svetlana N.'
'van de Streek, Jacco'
'Djanhan, Juste E.'
'Brüning, Jürgen'
'Alig, Edith'
'Bolte, Michael'
'Schmidt, Martin U.'
'Blaschka, Peter'
'Höffken, Hans Wolfgang'
'Erk, Peter'
_publ_section_title
;
 Structure determination of seven phases and solvates of Pigment Yellow
 183 and Pigment Yellow 191 from X-ray powder and single-crystal data
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              212
_journal_page_last               222
_journal_paper_doi               10.1107/S0108768109001827
_journal_volume                  65
_journal_year                    2009
_chemical_formula_sum            'C32 H46 Ca Cl2 N8 O11 S2'
_chemical_formula_weight         893.87
_chemical_name_common
'Pigment Yellow 183 dimethylacetamide tetrasolvate'
_chemical_name_systematic        ?
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.887(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9032(9)
_cell_length_b                   26.283(4)
_cell_length_c                   17.7857(18)
_cell_measurement_reflns_used    13733
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.1
_cell_measurement_theta_min      2.2
_cell_volume                     4152.3(9)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990) '
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_sigmaI/netI    0.0989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23644
_diffrn_reflns_theta_full        26.11
_diffrn_reflns_theta_max         26.11
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  0.9781
_exptl_absorpt_correction_T_min  0.8214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Spek, 1990; Blessing, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.313
_refine_diff_density_min         -0.670
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     522
_refine_ls_number_reflns         7640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0783
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1149P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1948
_refine_ls_wR_factor_ref         0.2110
_reflns_number_gt                4542
_reflns_number_total             7640
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            og5036.cif
_cod_data_source_block           PY1834DMAc
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2104325
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.1162(6) 0.56870(18) 1.0093(3) 0.0292(11) Uani d . 1 . .
H H1 0.128(8) 0.577(3) 0.965(4) 0.038(19) Uiso d . 1 . .
N N2 0.1837(5) 0.52859(17) 1.0391(3) 0.0289(11) Uani d . 1 . .
C C11 0.0352(6) 0.6002(2) 1.0565(3) 0.0264(12) Uani d . 1 . .
C C12 -0.0247(7) 0.6468(2) 1.0314(4) 0.0305(13) Uani d . 1 . .
S S12 0.01178(17) 0.67273(5) 0.94121(9) 0.0307(4) Uani d . 1 . .
O O121 0.0078(6) 0.62927(17) 0.8906(3) 0.0465(12) Uani d . 1 . .
O O122 0.1604(5) 0.69446(19) 0.9533(3) 0.0444(12) Uani d . 1 . .
O O123 -0.1066(5) 0.70939(17) 0.9233(3) 0.0405(11) Uani d . 1 . .
C C13 -0.1045(7) 0.6763(2) 1.0801(3) 0.0306(13) Uani d . 1 . .
H H13 -0.1504 0.7071 1.0624 0.037 Uiso calc R 1 . .
C C14 -0.1176(7) 0.6614(2) 1.1537(4) 0.0323(14) Uani d . 1 . .
Cl Cl14 -0.21028(19) 0.70085(6) 1.21442(10) 0.0425(4) Uani d . 1 . .
C C15 -0.0541(6) 0.6161(2) 1.1796(3) 0.0274(13) Uani d . 1 . .
Cl Cl15 -0.06420(18) 0.59616(6) 1.27138(8) 0.0369(4) Uani d . 1 . .
C C16 0.0204(7) 0.5851(2) 1.1311(3) 0.0290(13) Uani d . 1 . .
H H16 0.0615 0.5535 1.1485 0.035 Uiso calc R 1 . .
C C21 0.2605(7) 0.4990(2) 0.9966(3) 0.0259(12) Uani d . 1 . .
C C22 0.2850(7) 0.5037(2) 0.9153(3) 0.0273(12) Uani d . 1 . .
O O22 0.2345(5) 0.53597(15) 0.8712(2) 0.0332(10) Uani d . 1 . .
N N23 0.3812(5) 0.46359(17) 0.9029(3) 0.0268(11) Uani d . 1 . .
N N24 0.4172(6) 0.43484(17) 0.9697(3) 0.0281(11) Uani d . 1 . .
C C25 0.3455(7) 0.4554(2) 1.0234(3) 0.0280(13) Uani d . 1 . .
C C26 0.3568(8) 0.4353(2) 1.1026(3) 0.0341(14) Uani d . 1 . .
H H26A 0.2635 0.4175 1.1125 0.051 Uiso calc R 1 . .
H H26B 0.3726 0.4636 1.1381 0.051 Uiso calc R 1 . .
H H26C 0.4418 0.4116 1.1089 0.051 Uiso calc R 1 . .
C C31 0.4386(6) 0.4473(2) 0.8345(3) 0.0254(12) Uani d . 1 . .
C C32 0.3829(6) 0.4674(2) 0.7662(3) 0.0278(13) Uani d . 1 . .
H H32 0.3072 0.4930 0.7647 0.033 Uiso calc R 1 . .
C C33 0.4391(6) 0.4498(2) 0.6995(3) 0.0268(12) Uani d . 1 . .
S S33 0.35905(16) 0.47412(5) 0.61260(8) 0.0260(3) Uani d . 1 . .
O O331 0.3992(5) 0.43765(18) 0.5556(2) 0.0410(11) Uani d . 1 . .
O O332 0.1996(4) 0.47783(18) 0.6195(2) 0.0356(10) Uani d . 1 . .
O O333 0.4311(5) 0.52335(18) 0.6019(3) 0.0449(12) Uani d . 1 . .
C C34 0.5524(7) 0.4136(2) 0.7006(3) 0.0292(13) Uani d . 1 . .
H H34 0.5908 0.4022 0.6550 0.035 Uiso calc R 1 . .
C C35 0.6086(7) 0.3943(2) 0.7695(4) 0.0331(14) Uani d . 1 . .
H H35 0.6863 0.3695 0.7709 0.040 Uiso calc R 1 . .
C C36 0.5527(7) 0.4109(2) 0.8369(3) 0.0298(13) Uani d . 1 . .
H H36 0.5921 0.3975 0.8838 0.036 Uiso calc R 1 . .
Ca Ca1 0.52893(12) 0.40127(4) 0.46153(6) 0.0248(3) Uani d . 1 . .
O O1A 0.7410(4) 0.40046(16) 0.5425(2) 0.0319(9) Uani d . 1 . .
C C1A 0.8765(10) 0.3897(4) 0.5317(5) 0.064(2) Uani d . 1 . .
N N1A 0.9478(8) 0.3530(3) 0.5567(5) 0.070(2) Uani d . 1 . .
C C2A 0.8536(9) 0.3175(2) 0.6060(4) 0.0404(16) Uani d . 1 . .
H H2A1 0.7571 0.3338 0.6144 0.061 Uiso calc R 1 . .
H H2A2 0.9093 0.3115 0.6546 0.061 Uiso calc R 1 . .
H H2A3 0.8353 0.2850 0.5800 0.061 Uiso calc R 1 . .
C C3A 1.1054(8) 0.3394(3) 0.5458(5) 0.0486(18) Uani d . 1 . .
H H3A1 1.1249 0.3434 0.4925 0.073 Uiso calc R 1 . .
H H3A2 1.1233 0.3039 0.5609 0.073 Uiso calc R 1 . .
H H3A3 1.1729 0.3617 0.5766 0.073 Uiso calc R 1 . .
C C4A 0.9699(7) 0.4247(2) 0.4797(4) 0.0345(14) Uani d . 1 . .
H H4A1 1.0685 0.4320 0.5053 0.052 Uiso calc R 1 . .
H H4A2 0.9155 0.4566 0.4695 0.052 Uiso calc R 1 . .
H H4A3 0.9838 0.4071 0.4321 0.052 Uiso calc R 1 . .
O O1B 0.3219(5) 0.39733(18) 0.3806(3) 0.0416(11) Uani d . 1 . .
C C1B 0.2196(12) 0.4008(3) 0.3248(6) 0.071(3) Uani d . 1 . .
N N1B 0.1543(8) 0.4414(3) 0.3137(4) 0.065(2) Uani d . 1 . .
C C2B 0.1909(8) 0.4878(2) 0.3621(4) 0.0416(17) Uani d . 1 . .
H H2B1 0.2656 0.4787 0.4029 0.062 Uiso calc R 1 . .
H H2B2 0.0991 0.5000 0.3836 0.062 Uiso calc R 1 . .
H H2B3 0.2316 0.5146 0.3311 0.062 Uiso calc R 1 . .
C C3B 0.0292(8) 0.4485(3) 0.2523(4) 0.0451(17) Uani d . 1 . .
H H3B1 0.0174 0.4173 0.2224 0.068 Uiso calc R 1 . .
H H3B2 0.0545 0.4768 0.2196 0.068 Uiso calc R 1 . .
H H3B3 -0.0652 0.4561 0.2754 0.068 Uiso calc R 1 . .
C C4B 0.1817(8) 0.3559(3) 0.2747(4) 0.0440(17) Uani d . 1 . .
H H4B1 0.0724 0.3511 0.2701 0.066 Uiso calc R 1 . .
H H4B2 0.2301 0.3254 0.2966 0.066 Uiso calc R 1 . .
H H4B3 0.2180 0.3621 0.2247 0.066 Uiso calc R 1 . .
O O1C 0.4737(5) 0.32100(17) 0.5065(3) 0.0497(13) Uani d . 1 . .
C C1C 0.4650(9) 0.2787(3) 0.5313(8) 0.082(4) Uani d . 1 . .
N N1C 0.4770(7) 0.2366(3) 0.5112(6) 0.074(2) Uani d . 1 . .
C C2C 0.5251(11) 0.2360(4) 0.4305(5) 0.069(3) Uani d . 1 . .
H H2C1 0.5048 0.2693 0.4071 0.103 Uiso calc R 1 . .
H H2C2 0.4684 0.2097 0.4016 0.103 Uiso calc R 1 . .
H H2C3 0.6330 0.2286 0.4308 0.103 Uiso calc R 1 . .
C C3C 0.4663(8) 0.1870(2) 0.5485(5) 0.052(2) Uani d . 1 . .
H H3C1 0.5667 0.1761 0.5681 0.077 Uiso calc R 1 . .
H H3C2 0.4249 0.1618 0.5120 0.077 Uiso calc R 1 . .
H H3C3 0.4001 0.1898 0.5901 0.077 Uiso calc R 1 . .
C C4C 0.4236(9) 0.2769(3) 0.6247(5) 0.0527(19) Uani d . 1 . .
H H4C1 0.3317 0.2571 0.6296 0.079 Uiso calc R 1 . .
H H4C2 0.4086 0.3117 0.6428 0.079 Uiso calc R 1 . .
H H4C3 0.5073 0.2611 0.6548 0.079 Uiso calc R 1 . .
O O1D 0.6887(5) 0.36110(19) 0.3818(3) 0.0447(12) Uani d . 1 . .
C C1D 0.7091(7) 0.3458(2) 0.3168(3) 0.0311(13) Uani d . 1 . .
N N1D 0.8013(6) 0.30623(19) 0.3084(3) 0.0346(12) Uani d . 1 . .
C C2D 0.8762(8) 0.2805(3) 0.3708(5) 0.051(2) Uani d . 1 . .
H H2D1 0.8426 0.2946 0.4179 0.076 Uiso calc R 1 . .
H H2D2 0.9852 0.2852 0.3695 0.076 Uiso calc R 1 . .
H H2D3 0.8523 0.2442 0.3680 0.076 Uiso calc R 1 . .
C C3D 0.8224(8) 0.2819(3) 0.2351(4) 0.055(2) Uani d . 1 . .
H H3D1 0.7617 0.2509 0.2304 0.083 Uiso calc R 1 . .
H H3D2 0.9288 0.2734 0.2318 0.083 Uiso calc R 1 . .
H H3D3 0.7905 0.3055 0.1943 0.083 Uiso calc R 1 . .
C C4D 0.6313(9) 0.3707(3) 0.2491(4) 0.0506(19) Uani d . 1 . .
H H4D1 0.5646 0.3976 0.2654 0.076 Uiso calc R 1 . .
H H4D2 0.5719 0.3453 0.2197 0.076 Uiso calc R 1 . .
H H4D3 0.7066 0.3855 0.2178 0.076 Uiso calc R 1 . .
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'
Ca Ca 0.2262 0.3064 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C11 . . 118.1(5) ?
N2 N1 H1 . . 121(5) ?
C11 N1 H1 . . 120(5) ?
N1 N2 C21 . . 119.3(5) ?
C12 C11 C16 . . 119.6(5) ?
C12 C11 N1 . . 121.6(5) ?
C16 C11 N1 . . 118.8(5) ?
C13 C12 C11 . . 119.3(6) ?
C13 C12 S12 . . 118.4(4) ?
C11 C12 S12 . . 122.1(4) ?
O122 S12 O123 . . 114.6(3) ?
O122 S12 O121 . . 112.8(3) ?
O123 S12 O121 . . 113.6(3) ?
O122 S12 C12 . . 103.7(3) ?
O123 S12 C12 . . 106.1(3) ?
O121 S12 C12 . . 104.9(3) ?
C14 C13 C12 . . 120.8(6) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C13 C14 C15 . . 120.1(5) ?
C13 C14 Cl14 . . 119.6(5) ?
C15 C14 Cl14 . . 120.3(5) ?
C14 C15 C16 . . 120.0(5) ?
C14 C15 Cl15 . . 122.0(4) ?
C16 C15 Cl15 . . 117.9(5) ?
C15 C16 C11 . . 120.1(5) ?
C15 C16 H16 . . 119.9 ?
C11 C16 H16 . . 119.9 ?
N2 C21 C25 . . 124.5(5) ?
N2 C21 C22 . . 129.1(5) ?
C25 C21 C22 . . 106.4(4) ?
O22 C22 N23 . . 129.1(5) ?
O22 C22 C21 . . 127.8(5) ?
N23 C22 C21 . . 103.1(5) ?
C22 N23 C31 . . 129.1(5) ?
C22 N23 N24 . . 112.1(4) ?
C31 N23 N24 . . 118.8(4) ?
C25 N24 N23 . . 107.3(4) ?
N24 C25 C21 . . 111.2(5) ?
N24 C25 C26 . . 122.4(5) ?
C21 C25 C26 . . 126.4(5) ?
C25 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C25 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C32 C31 C36 . . 120.4(5) ?
C32 C31 N23 . . 120.6(5) ?
C36 C31 N23 . . 119.1(5) ?
C31 C32 C33 . . 119.4(5) ?
C31 C32 H32 . . 120.3 ?
C33 C32 H32 . . 120.3 ?
C34 C33 C32 . . 121.2(6) ?
C34 C33 S33 . . 120.5(4) ?
C32 C33 S33 . . 118.3(4) ?
O332 S33 O331 . . 113.2(3) ?
O332 S33 O333 . . 113.3(3) ?
O331 S33 O333 . . 111.2(3) ?
O332 S33 C33 . . 106.9(2) ?
O331 S33 C33 . . 105.4(3) ?
O333 S33 C33 . . 106.1(3) ?
S33 O331 Ca1 . . 159.5(3) ?
S33 O333 Ca1 . 3_666 154.4(3) ?
C33 C34 C35 . . 118.8(5) ?
C33 C34 H34 . . 120.6 ?
C35 C34 H34 . . 120.6 ?
C34 C35 C36 . . 121.0(5) ?
C34 C35 H35 . . 119.5 ?
C36 C35 H35 . . 119.5 ?
C31 C36 C35 . . 119.3(6) ?
C31 C36 H36 . . 120.4 ?
C35 C36 H36 . . 120.4 ?
O1B Ca1 O1A . . 176.77(17) ?
O1B Ca1 O331 . . 93.12(18) ?
O1A Ca1 O331 . . 88.85(16) ?
O1B Ca1 O333 . 3_666 82.80(18) ?
O1A Ca1 O333 . 3_666 99.56(17) ?
O331 Ca1 O333 . 3_666 95.74(18) ?
O1B Ca1 O1C . . 89.73(19) ?
O1A Ca1 O1C . . 87.71(18) ?
O331 Ca1 O1C . . 89.93(18) ?
O333 Ca1 O1C 3_666 . 170.8(2) ?
O1B Ca1 O1D . . 95.53(18) ?
O1A Ca1 O1D . . 82.38(16) ?
O331 Ca1 O1D . . 170.85(18) ?
O333 Ca1 O1D 3_666 . 88.31(18) ?
O1C Ca1 O1D . . 87.14(19) ?
C1A O1A Ca1 . . 131.2(5) ?
N1A C1A O1A . . 126.8(10) ?
N1A C1A C4A . . 113.0(8) ?
O1A C1A C4A . . 120.2(8) ?
C1A N1A C3A . . 128.4(9) ?
C1A N1A C2A . . 112.9(7) ?
C3A N1A C2A . . 118.7(7) ?
N1A C2A H2A1 . . 109.5 ?
N1A C2A H2A2 . . 109.5 ?
H2A1 C2A H2A2 . . 109.5 ?
N1A C2A H2A3 . . 109.5 ?
H2A1 C2A H2A3 . . 109.5 ?
H2A2 C2A H2A3 . . 109.5 ?
N1A C3A H3A1 . . 109.5 ?
N1A C3A H3A2 . . 109.5 ?
H3A1 C3A H3A2 . . 109.5 ?
N1A C3A H3A3 . . 109.5 ?
H3A1 C3A H3A3 . . 109.5 ?
H3A2 C3A H3A3 . . 109.5 ?
C1A C4A H4A1 . . 109.5 ?
C1A C4A H4A2 . . 109.5 ?
H4A1 C4A H4A2 . . 109.5 ?
C1A C4A H4A3 . . 109.5 ?
H4A1 C4A H4A3 . . 109.5 ?
H4A2 C4A H4A3 . . 109.5 ?
C1B O1B Ca1 . . 167.9(5) ?
N1B C1B O1B . . 119.0(9) ?
N1B C1B C4B . . 120.2(11) ?
O1B C1B C4B . . 120.8(8) ?
C1B N1B C2B . . 121.8(9) ?
C1B N1B C3B . . 122.8(9) ?
C2B N1B C3B . . 115.4(6) ?
N1B C2B H2B1 . . 109.5 ?
N1B C2B H2B2 . . 109.5 ?
H2B1 C2B H2B2 . . 109.5 ?
N1B C2B H2B3 . . 109.5 ?
H2B1 C2B H2B3 . . 109.5 ?
H2B2 C2B H2B3 . . 109.5 ?
N1B C3B H3B1 . . 109.5 ?
N1B C3B H3B2 . . 109.5 ?
H3B1 C3B H3B2 . . 109.5 ?
N1B C3B H3B3 . . 109.5 ?
H3B1 C3B H3B3 . . 109.5 ?
H3B2 C3B H3B3 . . 109.5 ?
C1B C4B H4B1 . . 109.5 ?
C1B C4B H4B2 . . 109.5 ?
H4B1 C4B H4B2 . . 109.5 ?
C1B C4B H4B3 . . 109.5 ?
H4B1 C4B H4B3 . . 109.5 ?
H4B2 C4B H4B3 . . 109.5 ?
C1C O1C Ca1 . . 171.5(5) ?
N1C C1C O1C . . 139.0(14) ?
N1C C1C C4C . . 107.3(9) ?
O1C C1C C4C . . 113.7(9) ?
C1C N1C C3C . . 133.8(11) ?
C1C N1C C2C . . 109.5(9) ?
C3C N1C C2C . . 116.5(8) ?
N1C C2C H2C1 . . 109.5 ?
N1C C2C H2C2 . . 109.5 ?
H2C1 C2C H2C2 . . 109.5 ?
N1C C2C H2C3 . . 109.5 ?
H2C1 C2C H2C3 . . 109.5 ?
H2C2 C2C H2C3 . . 109.5 ?
N1C C3C H3C1 . . 109.5 ?
N1C C3C H3C2 . . 109.5 ?
H3C1 C3C H3C2 . . 109.5 ?
N1C C3C H3C3 . . 109.5 ?
H3C1 C3C H3C3 . . 109.5 ?
H3C2 C3C H3C3 . . 109.5 ?
C1C C4C H4C1 . . 109.5 ?
C1C C4C H4C2 . . 109.5 ?
H4C1 C4C H4C2 . . 109.5 ?
C1C C4C H4C3 . . 109.5 ?
H4C1 C4C H4C3 . . 109.5 ?
H4C2 C4C H4C3 . . 109.5 ?
C1D O1D Ca1 . . 147.5(5) ?
O1D C1D N1D . . 118.9(6) ?
O1D C1D C4D . . 121.0(6) ?
N1D C1D C4D . . 120.1(6) ?
C1D N1D C2D . . 122.5(5) ?
C1D N1D C3D . . 123.4(6) ?
C2D N1D C3D . . 113.7(6) ?
N1D C2D H2D1 . . 109.5 ?
N1D C2D H2D2 . . 109.5 ?
H2D1 C2D H2D2 . . 109.5 ?
N1D C2D H2D3 . . 109.5 ?
H2D1 C2D H2D3 . . 109.5 ?
H2D2 C2D H2D3 . . 109.5 ?
N1D C3D H3D1 . . 109.5 ?
N1D C3D H3D2 . . 109.5 ?
H3D1 C3D H3D2 . . 109.5 ?
N1D C3D H3D3 . . 109.5 ?
H3D1 C3D H3D3 . . 109.5 ?
H3D2 C3D H3D3 . . 109.5 ?
C1D C4D H4D1 . . 109.5 ?
C1D C4D H4D2 . . 109.5 ?
H4D1 C4D H4D2 . . 109.5 ?
C1D C4D H4D3 . . 109.5 ?
H4D1 C4D H4D3 . . 109.5 ?
H4D2 C4D H4D3 . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . 1.307(7) ?
N1 C11 . 1.412(7) ?
N1 H1 . 0.83(7) ?
N2 C21 . 1.310(7) ?
C11 C12 . 1.395(8) ?
C11 C16 . 1.400(8) ?
C12 C13 . 1.394(8) ?
C12 S12 . 1.793(6) ?
S12 O122 . 1.444(5) ?
S12 O123 . 1.447(5) ?
S12 O121 . 1.453(5) ?
C13 C14 . 1.379(9) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.384(9) ?
C14 Cl14 . 1.744(5) ?
C15 C16 . 1.388(8) ?
C15 Cl15 . 1.723(6) ?
C16 H16 . 0.9500 ?
C21 C25 . 1.435(8) ?
C21 C22 . 1.481(8) ?
C22 O22 . 1.220(7) ?
C22 N23 . 1.386(7) ?
N23 C31 . 1.417(7) ?
N23 N24 . 1.426(7) ?
N24 C25 . 1.302(7) ?
C25 C26 . 1.503(8) ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C26 H26C . 0.9800 ?
C31 C32 . 1.386(8) ?
C31 C36 . 1.394(8) ?
C32 C33 . 1.396(7) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.386(8) ?
C33 S33 . 1.777(6) ?
S33 O332 . 1.437(4) ?
S33 O331 . 1.458(4) ?
S33 O333 . 1.462(5) ?
O331 Ca1 . 2.304(4) ?
O333 Ca1 3_666 2.320(4) ?
C34 C35 . 1.388(9) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.398(8) ?
C35 H35 . 0.9500 ?
C36 H36 . 0.9500 ?
Ca1 O1B . 2.263(5) ?
Ca1 O1A . 2.295(4) ?
Ca1 O333 3_666 2.320(4) ?
Ca1 O1C . 2.321(5) ?
Ca1 O1D . 2.328(4) ?
O1A C1A . 1.266(9) ?
C1A N1A . 1.221(12) ?
C1A C4A . 1.580(12) ?
N1A C3A . 1.474(9) ?
N1A C2A . 1.563(11) ?
C2A H2A1 . 0.9800 ?
C2A H2A2 . 0.9800 ?
C2A H2A3 . 0.9800 ?
C3A H3A1 . 0.9800 ?
C3A H3A2 . 0.9800 ?
C3A H3A3 . 0.9800 ?
C4A H4A1 . 0.9800 ?
C4A H4A2 . 0.9800 ?
C4A H4A3 . 0.9800 ?
O1B C1B . 1.304(13) ?
C1B N1B . 1.225(11) ?
C1B C4B . 1.503(11) ?
N1B C2B . 1.515(11) ?
N1B C3B . 1.517(11) ?
C2B H2B1 . 0.9800 ?
C2B H2B2 . 0.9800 ?
C2B H2B3 . 0.9800 ?
C3B H3B1 . 0.9800 ?
C3B H3B2 . 0.9800 ?
C3B H3B3 . 0.9800 ?
C4B H4B1 . 0.9800 ?
C4B H4B2 . 0.9800 ?
C4B H4B3 . 0.9800 ?
O1C C1C . 1.199(9) ?
C1C N1C . 1.170(11) ?
C1C C4C . 1.728(16) ?
N1C C3C . 1.470(10) ?
N1C C2C . 1.526(13) ?
C2C H2C1 . 0.9800 ?
C2C H2C2 . 0.9800 ?
C2C H2C3 . 0.9800 ?
C3C H3C1 . 0.9800 ?
C3C H3C2 . 0.9800 ?
C3C H3C3 . 0.9800 ?
C4C H4C1 . 0.9800 ?
C4C H4C2 . 0.9800 ?
C4C H4C3 . 0.9800 ?
O1D C1D . 1.248(7) ?
C1D N1D . 1.340(8) ?
C1D C4D . 1.499(10) ?
N1D C2D . 1.427(10) ?
N1D C3D . 1.475(8) ?
C2D H2D1 . 0.9800 ?
C2D H2D2 . 0.9800 ?
C2D H2D3 . 0.9800 ?
C3D H3D1 . 0.9800 ?
C3D H3D2 . 0.9800 ?
C3D H3D3 . 0.9800 ?
C4D H4D1 . 0.9800 ?
C4D H4D2 . 0.9800 ?
C4D H4D3 . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O121 . 0.83(7) 2.14(7) 2.764(7) 132(6)
N1 H1 O22 . 0.83(7) 2.26(7) 2.868(6) 131(6)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 N2 C21 . . . . -179.5(5) ?
N2 N1 C11 C12 . . . . 172.3(6) ?
N2 N1 C11 C16 . . . . -5.1(8) ?
C16 C11 C12 C13 . . . . -3.0(9) ?
N1 C11 C12 C13 . . . . 179.6(5) ?
C16 C11 C12 S12 . . . . 171.3(5) ?
N1 C11 C12 S12 . . . . -6.1(8) ?
C13 C12 S12 O122 . . . . 95.1(5) ?
C11 C12 S12 O122 . . . . -79.3(6) ?
C13 C12 S12 O123 . . . . -26.0(6) ?
C11 C12 S12 O123 . . . . 159.7(5) ?
C13 C12 S12 O121 . . . . -146.5(5) ?
C11 C12 S12 O121 . . . . 39.2(6) ?
C11 C12 C13 C14 . . . . 3.6(9) ?
S12 C12 C13 C14 . . . . -170.9(5) ?
C12 C13 C14 C15 . . . . -1.5(9) ?
C12 C13 C14 Cl14 . . . . 176.8(5) ?
C13 C14 C15 C16 . . . . -1.3(9) ?
Cl14 C14 C15 C16 . . . . -179.5(5) ?
C13 C14 C15 Cl15 . . . . 178.8(5) ?
Cl14 C14 C15 Cl15 . . . . 0.6(8) ?
C14 C15 C16 C11 . . . . 1.8(9) ?
Cl15 C15 C16 C11 . . . . -178.3(5) ?
C12 C11 C16 C15 . . . . 0.3(9) ?
N1 C11 C16 C15 . . . . 177.8(5) ?
N1 N2 C21 C25 . . . . 176.7(6) ?
N1 N2 C21 C22 . . . . 0.0(9) ?
N2 C21 C22 O22 . . . . -2.0(11) ?
C25 C21 C22 O22 . . . . -179.2(6) ?
N2 C21 C22 N23 . . . . 176.6(6) ?
C25 C21 C22 N23 . . . . -0.5(6) ?
O22 C22 N23 C31 . . . . -4.7(11) ?
C21 C22 N23 C31 . . . . 176.7(5) ?
O22 C22 N23 N24 . . . . 178.7(6) ?
C21 C22 N23 N24 . . . . 0.0(6) ?
C22 N23 N24 C25 . . . . 0.5(7) ?
C31 N23 N24 C25 . . . . -176.5(5) ?
N23 N24 C25 C21 . . . . -0.9(7) ?
N23 N24 C25 C26 . . . . -179.8(5) ?
N2 C21 C25 N24 . . . . -176.4(6) ?
C22 C21 C25 N24 . . . . 0.9(7) ?
N2 C21 C25 C26 . . . . 2.4(10) ?
C22 C21 C25 C26 . . . . 179.7(6) ?
C22 N23 C31 C32 . . . . -9.7(9) ?
N24 N23 C31 C32 . . . . 166.8(5) ?
C22 N23 C31 C36 . . . . 169.9(6) ?
N24 N23 C31 C36 . . . . -13.6(8) ?
C36 C31 C32 C33 . . . . 1.9(8) ?
N23 C31 C32 C33 . . . . -178.5(5) ?
C31 C32 C33 C34 . . . . -1.8(9) ?
C31 C32 C33 S33 . . . . 177.0(4) ?
C34 C33 S33 O332 . . . . 138.8(5) ?
C32 C33 S33 O332 . . . . -40.0(5) ?
C34 C33 S33 O331 . . . . 18.0(5) ?
C32 C33 S33 O331 . . . . -160.7(5) ?
C34 C33 S33 O333 . . . . -100.0(5) ?
C32 C33 S33 O333 . . . . 81.2(5) ?
O332 S33 O331 Ca1 . . . . 146.3(8) ?
O333 S33 O331 Ca1 . . . . 17.4(10) ?
C33 S33 O331 Ca1 . . . . -97.2(9) ?
O332 S33 O333 Ca1 . . . 3_666 -61.6(8) ?
O331 S33 O333 Ca1 . . . 3_666 67.2(8) ?
C33 S33 O333 Ca1 . . . 3_666 -178.6(7) ?
C32 C33 C34 C35 . . . . 0.8(9) ?
S33 C33 C34 C35 . . . . -177.9(4) ?
C33 C34 C35 C36 . . . . 0.0(9) ?
C32 C31 C36 C35 . . . . -1.0(9) ?
N23 C31 C36 C35 . . . . 179.3(5) ?
C34 C35 C36 C31 . . . . 0.1(9) ?
S33 O331 Ca1 O1B . . . . -123.8(9) ?
S33 O331 Ca1 O1A . . . . 58.8(9) ?
S33 O331 Ca1 O333 . . . 3_666 -40.7(9) ?
S33 O331 Ca1 O1C . . . . 146.5(9) ?
S33 O331 Ca1 O1D . . . . 75.3(15) ?
O1B Ca1 O1A C1A . . . . 60(3) ?
O331 Ca1 O1A C1A . . . . -172.3(7) ?
O333 Ca1 O1A C1A 3_666 . . . -76.7(8) ?
O1C Ca1 O1A C1A . . . . 97.7(8) ?
O1D Ca1 O1A C1A . . . . 10.3(7) ?
Ca1 O1A C1A N1A . . . . -112.1(9) ?
Ca1 O1A C1A C4A . . . . 66.4(9) ?
O1A C1A N1A C3A . . . . -179.7(7) ?
C4A C1A N1A C3A . . . . 1.8(13) ?
O1A C1A N1A C2A . . . . 0.4(13) ?
C4A C1A N1A C2A . . . . -178.2(6) ?
O1A Ca1 O1B C1B . . . . -110(3) ?
O331 Ca1 O1B C1B . . . . 122(2) ?
O333 Ca1 O1B C1B 3_666 . . . 27(2) ?
O1C Ca1 O1B C1B . . . . -148(2) ?
O1D Ca1 O1B C1B . . . . -61(2) ?
Ca1 O1B C1B N1B . . . . -73(3) ?
Ca1 O1B C1B C4B . . . . 107(2) ?
O1B C1B N1B C2B . . . . 1.0(10) ?
C4B C1B N1B C2B . . . . -179.0(6) ?
O1B C1B N1B C3B . . . . -177.3(6) ?
C4B C1B N1B C3B . . . . 2.6(10) ?
O1B Ca1 O1C C1C . . . . 148(5) ?
O1A Ca1 O1C C1C . . . . -30(5) ?
O331 Ca1 O1C C1C . . . . -119(5) ?
O333 Ca1 O1C C1C 3_666 . . . 113(5) ?
O1D Ca1 O1C C1C . . . . 53(5) ?
Ca1 O1C C1C N1C . . . . -80(5) ?
Ca1 O1C C1C C4C . . . . 100(5) ?
O1C C1C N1C C3C . . . . 178.4(9) ?
C4C C1C N1C C3C . . . . -1.0(11) ?
O1C C1C N1C C2C . . . . 3.6(14) ?
C4C C1C N1C C2C . . . . -175.8(6) ?
O1B Ca1 O1D C1D . . . . 13.0(8) ?
O1A Ca1 O1D C1D . . . . -169.5(8) ?
O331 Ca1 O1D C1D . . . . 173.9(10) ?
O333 Ca1 O1D C1D 3_666 . . . -69.6(8) ?
O1C Ca1 O1D C1D . . . . 102.5(8) ?
Ca1 O1D C1D N1D . . . . -152.5(6) ?
Ca1 O1D C1D C4D . . . . 27.0(11) ?
O1D C1D N1D C2D . . . . 0.6(9) ?
C4D C1D N1D C2D . . . . -178.9(6) ?
O1D C1D N1D C3D . . . . 174.0(6) ?
C4D C1D N1D C3D . . . . -5.6(9) ?
