#------------------------------------------------------------------------------
#$Date: 2019-11-22 19:37:04 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231349 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/65/4516511.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4516511
loop_
_publ_author_name
'Sangtani, Ekta'
'Sahu, Sanjay K.'
'Thorat, Shridhar H.'
'Gawade, Rupesh L.'
'Jha, Kunal K.'
'Munshi, Parthapratim'
'Gonnade, Rajesh G.'
_publ_section_title
;
 Furosemide Cocrystals with Pyridines: An Interesting Case of Color
 Cocrystal Polymorphism
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5858
_journal_paper_doi               10.1021/acs.cgd.5b01240
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C39 H34 Cl2 N7 O10 S2'
_chemical_formula_weight         895.75
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                107.1600(10)
_cell_angle_beta                 107.3050(10)
_cell_angle_gamma                91.4320(10)
_cell_formula_units_Z            2
_cell_length_a                   10.2035(2)
_cell_length_b                   14.0538(3)
_cell_length_c                   15.1873(3)
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.60
_cell_measurement_theta_min      2.87
_cell_volume                     1971.46(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41374
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         1.481
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.9508
_exptl_absorpt_correction_T_min  0.8816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS(BRUKER,2006)
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             926
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.563
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     575
_refine_ls_number_reflns         9494
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      2.558
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0673
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8425
_reflns_number_total             9494
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5b01240_si_002.cif
_cod_data_source_block           2_FS_2BP
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1971.45(7)
_cod_database_code               4516511
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.882
_shelx_estimated_absorpt_t_max   0.951
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.49503(4) 0.84681(3) 0.47009(3) 0.01509(10) Uani 1 1 d . . . . .
Cl1' Cl 0.95852(4) 0.87752(3) 0.44773(3) 0.01571(10) Uani 1 1 d . . . . .
S1 S 0.24038(4) 0.92158(3) 0.33724(3) 0.01135(10) Uani 1 1 d . . . . .
S1' S 0.69751(5) 0.91719(3) 0.27668(3) 0.01136(10) Uani 1 1 d . . . . .
O1 O -0.11896(12) 0.59619(9) 0.17602(9) 0.0164(3) Uani 1 1 d . . . . .
H1O H -0.1888 0.5529 0.1472 0.025 Uiso 1 1 calc R U . . .
O2 O -0.03527(12) 0.47412(9) 0.23501(8) 0.0175(3) Uani 1 1 d . . . . .
O3 O 0.23405(13) 0.31052(10) 0.40841(9) 0.0229(3) Uani 1 1 d . . . . .
O4 O 0.35455(12) 0.94175(9) 0.30540(8) 0.0152(3) Uani 1 1 d . . . . .
O5 O 0.23867(12) 0.98344(9) 0.43081(8) 0.0145(3) Uani 1 1 d . . . . .
O1' O 0.36744(12) 0.59259(9) 0.16539(9) 0.0165(3) Uani 1 1 d . . . . .
H1'O H 0.2994 0.5476 0.1403 0.025 Uiso 1 1 calc R U . . .
O2' O 0.46130(12) 0.48017(9) 0.23545(8) 0.0158(3) Uani 1 1 d . . . . .
O3' O 0.71692(15) 0.34430(10) 0.40880(9) 0.0282(3) Uani 1 1 d . . . . .
O4' O 0.83129(12) 0.95404(9) 0.27873(8) 0.0175(3) Uani 1 1 d . . . . .
O5' O 0.58444(12) 0.89891(9) 0.18866(8) 0.0160(3) Uani 1 1 d . . . . .
N1 N 0.22197(14) 0.50332(11) 0.35237(10) 0.0147(3) Uani 1 1 d . . . . .
H1N H 0.1433 0.4634 0.3235 0.018 Uiso 1 1 calc R U . . .
N2 N 0.10240(16) 0.92641(12) 0.25596(11) 0.0156(4) Uani 1 1 d . . . . .
N3' N 0.63975(15) 0.45743(11) 0.08070(10) 0.0155(3) Uani 1 1 d . . . . .
N3 N 0.85951(15) 0.54611(11) 0.92388(10) 0.0145(3) Uani 1 1 d . . . . .
N4 N 0.14933(15) 0.97052(11) 1.08250(9) 0.0152(3) Uani 1 1 d . . . . .
N1' N 0.71781(15) 0.52740(10) 0.35684(10) 0.0150(3) Uani 1 1 d . . . . .
H1'N H 0.6419 0.4844 0.3300 0.018 Uiso 1 1 calc R U . . .
N2' N 0.65663(19) 0.99923(12) 0.36035(12) 0.0140(3) Uani 1 1 d . . . . .
C1 C 0.22414(18) 0.59757(13) 0.34734(12) 0.0121(4) Uani 1 1 d . . . . .
C2 C 0.34224(18) 0.66842(13) 0.40160(12) 0.0127(4) Uani 1 1 d . . . . .
H2 H 0.4204 0.6491 0.4419 0.015 Uiso 1 1 calc R U . . .
C3 C 0.34677(17) 0.76423(13) 0.39755(11) 0.0119(4) Uani 1 1 d . . . . .
C4 C 0.23385(17) 0.79610(13) 0.33749(11) 0.0107(4) Uani 1 1 d . . . . .
C5 C 0.11800(18) 0.72708(13) 0.28411(11) 0.0115(4) Uani 1 1 d . . . . .
H5 H 0.0414 0.7473 0.2433 0.014 Uiso 1 1 calc R U . . .
C6 C 0.10808(17) 0.62932(13) 0.28726(11) 0.0113(4) Uani 1 1 d . . . . .
C7 C -0.01931(18) 0.55900(14) 0.23137(12) 0.0132(4) Uani 1 1 d . . . . .
C8 C 0.34279(18) 0.46353(13) 0.40302(12) 0.0144(4) Uani 1 1 d . . . . .
H8A H 0.3604 0.4905 0.4741 0.017 Uiso 1 1 calc R U . . .
H8B H 0.4253 0.4852 0.3890 0.017 Uiso 1 1 calc R U . . .
C9 C 0.31890(18) 0.35239(14) 0.37115(12) 0.0153(4) Uani 1 1 d . . . . .
C10 C 0.3583(2) 0.28006(15) 0.30794(13) 0.0243(5) Uani 1 1 d . . . . .
H10 H 0.4172 0.2891 0.2722 0.029 Uiso 1 1 calc R U . . .
C11 C 0.2950(2) 0.18688(15) 0.30448(13) 0.0269(5) Uani 1 1 d . . . . .
H11 H 0.3034 0.1218 0.2661 0.032 Uiso 1 1 calc R U . . .
C12 C 0.2217(2) 0.20883(15) 0.36560(14) 0.0271(5) Uani 1 1 d . . . . .
H12 H 0.1683 0.1608 0.3778 0.032 Uiso 1 1 calc R U . . .
C13' C 0.6635(2) 0.37722(14) 0.11144(13) 0.0200(4) Uani 1 1 d . . . . .
H13' H 0.7513 0.3784 0.1568 0.024 Uiso 1 1 calc R U . . .
C14' C 0.56837(19) 0.29327(14) 0.08124(13) 0.0209(4) Uani 1 1 d . . . . .
H14' H 0.5900 0.2388 0.1058 0.025 Uiso 1 1 calc R U . . .
C15' C 0.44135(19) 0.29021(14) 0.01468(12) 0.0203(4) Uani 1 1 d . . . . .
H15' H 0.3740 0.2331 -0.0084 0.024 Uiso 1 1 calc R U . . .
C16' C 0.41395(19) 0.37204(14) -0.01783(12) 0.0172(4) Uani 1 1 d . . . . .
H16' H 0.3268 0.3717 -0.0635 0.021 Uiso 1 1 calc R U . . .
C17' C 0.51369(18) 0.45463(13) 0.01629(12) 0.0136(4) Uani 1 1 d . . . . .
C13 C 0.83405(19) 0.62730(14) 0.89560(12) 0.0177(4) Uani 1 1 d . . . . .
H13 H 0.7447 0.6275 0.8528 0.021 Uiso 1 1 calc R U . . .
C14 C 0.9297(2) 0.71066(14) 0.92479(13) 0.0232(5) Uani 1 1 d . . . . .
H14 H 0.9068 0.7668 0.9030 0.028 Uiso 1 1 calc R U . . .
C15 C 1.0593(2) 0.71008(15) 0.98652(14) 0.0312(5) Uani 1 1 d . . . . .
H15 H 1.1283 0.7659 1.0077 0.037 Uiso 1 1 calc R U . . .
C16 C 1.0879(2) 0.62742(15) 1.01726(14) 0.0266(5) Uani 1 1 d . . . . .
H16 H 1.1766 0.6264 1.0604 0.032 Uiso 1 1 calc R U . . .
C17 C 0.98692(18) 0.54600(13) 0.98505(12) 0.0146(4) Uani 1 1 d . . . . .
C18 C 0.28058(18) 0.95506(13) 1.08972(12) 0.0158(4) Uani 1 1 d . . . . .
H18 H 0.3350 0.9408 1.1459 0.019 Uiso 1 1 calc R U . . .
C19 C 0.3416(2) 0.95852(15) 1.02129(13) 0.0237(5) Uani 1 1 d . . . . .
H19 H 0.4274 0.9332 1.0224 0.028 Uiso 1 1 calc R U . A 1
C20' C 0.2740(12) 1.0002(6) 0.9502(9) 0.027(2) Uani 0.45 1 d . U P B 1
H20' H 0.3185 1.0163 0.9088 0.032 Uiso 0.45 1 calc R U P B 1
C21' C 0.1363(12) 1.0174(6) 0.9428(8) 0.027(2) Uani 0.45 1 d . U P B 1
H21' H 0.0864 1.0472 0.8964 0.033 Uiso 0.45 1 calc R U P B 1
C20 C 0.2524(10) 0.9606(5) 0.9314(7) 0.0241(17) Uani 0.55 1 d . U P B 2
H20 H 0.2858 0.9513 0.8777 0.029 Uiso 0.55 1 calc R U P B 2
C21 C 0.1196(10) 0.9758(4) 0.9214(7) 0.0243(17) Uani 0.55 1 d . U P B 2
H21 H 0.0584 0.9764 0.8607 0.029 Uiso 0.55 1 calc R U P B 2
C22 C 0.07284(19) 0.99085(15) 1.00313(13) 0.0213(5) Uani 1 1 d . . . . .
C1' C 0.71214(18) 0.61783(13) 0.34235(11) 0.0111(4) Uani 1 1 d . . . . .
C2' C 0.82265(18) 0.69527(13) 0.39365(12) 0.0119(4) Uani 1 1 d . . . . .
H2' H 0.9004 0.6847 0.4413 0.014 Uiso 1 1 calc R U . . .
C3' C 0.82052(17) 0.78526(13) 0.37633(11) 0.0104(4) Uani 1 1 d . . . . .
C4' C 0.70913(17) 0.80374(13) 0.30473(11) 0.0103(4) Uani 1 1 d . . . . .
C5' C 0.59712(18) 0.72933(13) 0.25716(11) 0.0112(4) Uani 1 1 d . . . . .
H5' H 0.5193 0.7415 0.2107 0.013 Uiso 1 1 calc R U . . .
C6' C 0.59402(17) 0.63787(13) 0.27456(11) 0.0109(4) Uani 1 1 d . . . . .
C7' C 0.47063(18) 0.56258(14) 0.22423(11) 0.0126(4) Uani 1 1 d . . . . .
C8' C 0.84130(18) 0.49607(13) 0.41400(12) 0.0146(4) Uani 1 1 d . . . . .
H8A' H 0.8554 0.5273 0.4842 0.017 Uiso 1 1 calc R U . . .
H8B' H 0.9236 0.5182 0.4000 0.017 Uiso 1 1 calc R U . . .
C9' C 0.82370(18) 0.38516(13) 0.38873(12) 0.0153(4) Uani 1 1 d . . . . .
C10' C 0.8885(2) 0.31161(14) 0.34767(14) 0.0253(5) Uani 1 1 d . . . . .
H10' H 0.9657 0.3197 0.3266 0.030 Uiso 1 1 calc R U . . .
C11' C 0.8200(2) 0.21872(15) 0.34147(13) 0.0245(5) Uani 1 1 d . . . . .
H11' H 0.8428 0.1534 0.3160 0.029 Uiso 1 1 calc R U . . .
C12' C 0.7179(2) 0.24230(15) 0.37860(14) 0.0283(5) Uani 1 1 d . . . . .
H12' H 0.6545 0.1950 0.3835 0.034 Uiso 1 1 calc R U . . .
H2'N H 0.712(2) 1.0113(15) 0.4152(15) 0.036(7) Uiso 1 1 d . . . . .
H3'N H 0.575(2) 0.9851(15) 0.3560(13) 0.029(6) Uiso 1 1 d . . . . .
H2N H 0.028(2) 0.9368(16) 0.2702(14) 0.044 Uiso 1 1 d . U . . .
H3N H 0.112(2) 0.9373(16) 0.2102(15) 0.044 Uiso 1 1 d . U . . .
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O5 S1 O4 118.18(8) . 1
O5 S1 O4 118.18(8) . .
O4 S1 O4 0.00(9) 1 .
O5 S1 N2 109.51(7) . .
O4 S1 N2 107.22(7) 1 .
O4 S1 N2 107.22(7) . .
O5 S1 C4 107.44(7) . .
O4 S1 C4 108.14(7) 1 .
O4 S1 C4 108.14(7) . .
N2 S1 C4 105.67(9) . .
O5' S1' O4' 118.02(7) . .
O5' S1' N2' 106.69(8) . .
O4' S1' N2' 107.19(9) . .
O5' S1' C4' 107.14(8) . .
O4' S1' C4' 108.92(7) . .
N2' S1' C4' 108.57(8) . .
C7 O1 H1O 109.5 . .
O2 O2 C7 0(10) 1 .
C12 O3 C9 106.38(13) . .
O4 O4 S1 0(10) 1 .
C7' O1' H1'O 109.5 . .
O2' O2' C7' 0(10) 1 .
C9' O3' C12' 106.54(13) . .
C1 N1 C8 123.90(15) . .
C1 N1 H1N 118.0 . .
C8 N1 H1N 118.0 . .
S1 N2 H2N 120.0(13) . .
S1 N2 H3N 115.9(17) . .
H2N N2 H3N 121(2) . .
C13' N3' C17' 117.15(17) . .
C13 N3 C17 117.97(17) . .
C18 N4 C22 117.67(14) . .
C1' N1' C8' 124.54(15) . .
C1' N1' H1'N 117.7 . .
C8' N1' H1'N 117.7 . .
S1' N2' H2'N 114.5(13) . .
S1' N2' H3'N 110.1(13) . .
H2'N N2' H3'N 114.5(19) . .
N1 C1 C2 120.47(15) . .
N1 C1 C6 121.78(16) . .
C2 C1 C6 117.75(16) . .
C3 C2 C1 121.46(15) . .
C3 C2 H2 119.3 . .
C1 C2 H2 119.3 . .
C2 C3 C4 121.37(17) . .
C2 C3 Cl1 117.86(12) . .
C4 C3 Cl1 120.76(14) . .
C5 C4 C3 117.44(16) . .
C5 C4 S1 122.19(12) . .
C3 C4 S1 120.28(14) . .
C4 C5 C6 123.09(15) . .
C4 C5 H5 118.5 . .
C6 C5 H5 118.5 . .
C5 C6 C1 118.86(16) . .
C5 C6 C7 121.29(14) . .
C1 C6 C7 119.85(16) . .
O2 C7 O2 0.00(12) 1 .
O2 C7 O1 121.84(17) 1 .
O2 C7 O1 121.84(17) . .
O2 C7 C6 123.76(15) 1 .
O2 C7 C6 123.76(15) . .
O1 C7 C6 114.40(15) . .
N1 C8 C9 110.28(15) . .
N1 C8 H8A 109.6 . .
C9 C8 H8A 109.6 . .
N1 C8 H8B 109.6 . .
C9 C8 H8B 109.6 . .
H8A C8 H8B 108.1 . .
C10 C9 O3 109.81(16) . .
C10 C9 C8 133.45(17) . .
O3 C9 C8 116.66(14) . .
C9 C10 C11 106.85(17) . .
C9 C10 H10 126.6 . .
C11 C10 H10 126.6 . .
C12 C11 C10 106.59(18) . .
C12 C11 H11 126.7 . .
C10 C11 H11 126.7 . .
C11 C12 O3 110.38(18) . .
C11 C12 H12 124.8 . .
O3 C12 H12 124.8 . .
N3' C13' C14' 124.05(17) . .
N3' C13' H13' 118.0 . .
C14' C13' H13' 118.0 . .
C15' C14' C13' 118.53(17) . .
C15' C14' H14' 120.7 . .
C13' C14' H14' 120.7 . .
C14' C15' C16' 118.58(19) . .
C14' C15' H15' 120.7 . .
C16' C15' H15' 120.7 . .
C15' C16' C17' 120.00(17) . .
C15' C16' H16' 120.0 . .
C17' C16' H16' 120.0 . .
N3' C17' C16' 121.68(15) . .
N3' C17' C17' 117.0(2) . 2_665
C16' C17' C17' 121.3(2) . 2_665
N3 C13 C14 123.96(17) . .
N3 C13 H13 118.0 . .
C14 C13 H13 118.0 . .
C15 C14 C13 117.93(17) . .
C15 C14 H14 121.0 . .
C13 C14 H14 121.0 . .
C14 C15 C16 119.2(2) . .
C14 C15 H15 120.4 . .
C16 C15 H15 120.4 . .
C15 C16 C17 119.92(18) . .
C15 C16 H16 120.0 . .
C17 C16 H16 120.0 . .
N3 C17 C16 121.01(16) . .
N3 C17 C17 116.9(2) . 2_767
C16 C17 C17 122.1(2) . 2_767
N4 C18 C19 124.33(15) . .
N4 C18 H18 117.8 . .
C19 C18 H18 117.8 . .
C18 C19 C20' 117.9(6) . .
C18 C19 C20 116.3(5) . .
C18 C19 H19 121.0 . .
C20' C19 H19 121.0 . .
C19 C20' C21' 116.6(11) . .
C19 C20' H20' 121.7 . .
C21' C20' H20' 121.7 . .
C22 C21' C20' 120.4(10) . .
C22 C21' H21' 119.8 . .
C20' C21' H21' 119.8 . .
C21 C20 C19 120.0(9) . .
C21 C20 H20 120.0 . .
C19 C20 H20 120.0 . .
C20 C21 C22 118.9(8) . .
C20 C21 H21 120.5 . .
C22 C21 H21 120.5 . .
N4 C22 C21' 120.1(5) . .
N4 C22 C21 120.5(4) . .
N4 C22 C22 116.94(18) . 2_577
C21' C22 C22 121.1(5) . 2_577
C21 C22 C22 121.4(4) . 2_577
N1' C1' C2' 120.94(15) . .
N1' C1' C6' 121.19(17) . .
C2' C1' C6' 117.87(15) . .
C3' C2' C1' 121.35(15) . .
C3' C2' H2' 119.3 . .
C1' C2' H2' 119.3 . .
C2' C3' C4' 121.48(17) . .
C2' C3' Cl1' 117.49(13) . .
C4' C3' Cl1' 121.01(13) . .
C5' C4' C3' 117.28(15) . .
C5' C4' S1' 117.83(12) . .
C3' C4' S1' 124.77(14) . .
C4' C5' C6' 122.78(15) . .
C4' C5' H5' 118.6 . .
C6' C5' H5' 118.6 . .
C5' C6' C1' 119.00(17) . .
C5' C6' C7' 120.58(15) . .
C1' C6' C7' 120.41(15) . .
O2' C7' O2' 0.00(12) 1 .
O2' C7' O1' 122.21(17) 1 .
O2' C7' O1' 122.21(17) . .
O2' C7' C6' 124.03(15) 1 .
O2' C7' C6' 124.03(15) . .
O1' C7' C6' 113.76(15) . .
N1' C8' C9' 109.20(15) . .
N1' C8' H8A' 109.8 . .
C9' C8' H8A' 109.8 . .
N1' C8' H8B' 109.8 . .
C9' C8' H8B' 109.8 . .
H8A' C8' H8B' 108.3 . .
C10' C9' O3' 109.40(16) . .
C10' C9' C8' 134.45(18) . .
O3' C9' C8' 116.14(14) . .
C9' C10' C11' 107.31(18) . .
C9' C10' H10' 126.3 . .
C11' C10' H10' 126.3 . .
C12' C11' C10' 106.14(17) . .
C12' C11' H11' 126.9 . .
C10' C11' H11' 126.9 . .
C11' C12' O3' 110.60(18) . .
C11' C12' H12' 124.7 . .
O3' C12' H12' 124.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C3 1.7365(19) .
Cl1' C3' 1.7350(18) .
S1 O5 1.4360(11) .
S1 O4 1.4390(11) 1
S1 O4 1.4390(11) .
S1 N2 1.5909(15) .
S1 C4 1.7642(17) .
S1' O5' 1.4315(12) .
S1' O4' 1.4360(12) .
S1' N2' 1.6101(15) .
S1' C4' 1.7659(16) .
O1 C7 1.3382(18) .
O1 H1O 0.8400 .
O2 O2 0.000(3) 1
O2 C7 1.220(2) .
O3 C12 1.369(2) .
O3 C9 1.370(2) .
O4 O4 0.000(3) 1
O1' C7' 1.3303(18) .
O1' H1'O 0.8400 .
O2' O2' 0.000(3) 1
O2' C7' 1.2248(19) .
O3' C9' 1.371(2) .
O3' C12' 1.371(2) .
N1 C1 1.349(2) .
N1 C8 1.4657(19) .
N1 H1N 0.8800 .
N2 H2N 0.85(2) .
N2 H3N 0.79(2) .
N3' C13' 1.343(2) .
N3' C17' 1.356(2) .
N3 C13 1.339(2) .
N3 C17 1.355(2) .
N4 C18 1.339(2) .
N4 C22 1.341(2) .
N1' C1' 1.352(2) .
N1' C8' 1.4621(19) .
N1' H1'N 0.8800 .
N2' H2'N 0.82(2) .
N2' H3'N 0.83(2) .
C1 C2 1.410(2) .
C1 C6 1.435(2) .
C2 C3 1.366(2) .
C2 H2 0.9500 .
C3 C4 1.415(2) .
C4 C5 1.380(2) .
C5 C6 1.391(2) .
C5 H5 0.9500 .
C6 C7 1.474(2) .
C7 O2 1.220(2) 1
C8 C9 1.483(2) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.338(2) .
C10 C11 1.426(3) .
C10 H10 0.9500 .
C11 C12 1.331(2) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13' C14' 1.380(3) .
C13' H13' 0.9500 .
C14' C15' 1.377(2) .
C14' H14' 0.9500 .
C15' C16' 1.383(2) .
C15' H15' 0.9500 .
C16' C17' 1.387(3) .
C16' H16' 0.9500 .
C17' C17' 1.502(3) 2_665
C13 C14 1.378(3) .
C13 H13 0.9500 .
C14 C15 1.377(2) .
C14 H14 0.9500 .
C15 C16 1.381(2) .
C15 H15 0.9500 .
C16 C17 1.386(3) .
C16 H16 0.9500 .
C17 C17 1.497(3) 2_767
C18 C19 1.373(2) .
C18 H18 0.9500 .
C19 C20' 1.391(13) .
C19 C20 1.407(11) .
C19 H19 0.9500 .
C20' C21' 1.409(17) .
C20' H20' 0.9500 .
C21' C22 1.392(13) .
C21' H21' 0.9500 .
C20 C21 1.348(14) .
C20 H20 0.9500 .
C21 C22 1.420(10) .
C21 H21 0.9500 .
C22 C22 1.495(3) 2_577
C1' C2' 1.407(2) .
C1' C6' 1.429(2) .
C2' C3' 1.365(2) .
C2' H2' 0.9500 .
C3' C4' 1.410(2) .
C4' C5' 1.387(2) .
C5' C6' 1.388(2) .
C5' H5' 0.9500 .
C6' C7' 1.474(2) .
C7' O2' 1.2248(19) 1
C8' C9' 1.484(2) .
C8' H8A' 0.9900 .
C8' H8B' 0.9900 .
C9' C10' 1.339(2) .
C10' C11' 1.430(3) .
C10' H10' 0.9500 .
C11' C12' 1.330(2) .
C11' H11' 0.9500 .
C12' H12' 0.9500 .
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
O1' H1'O N3 0.84 1.87 2.711(2) 174.6 2_666
O1 H1O N3' 0.84 1.98 2.817(2) 176.6 1_455
N2' H3'N O4 0.83(2) 2.16(2) 2.966(2) 165.2(17) 1
N2' H2'N O5 0.82(2) 2.22(2) 2.9625(19) 150.9(19) 2_676
N2 H2N O4' 0.85(2) 2.07(2) 2.9098(19) 170.0(19) 1_455
N2 H3N N4 0.79(2) 2.26(2) 3.0419(19) 178(2) 1_554
C10' H10' O3 0.95 2.67 3.370(2) 130.7 1_655
C8 H8B O2' 0.99 2.45 3.188(2) 131.2 1
C8' H8B' O2 0.99 2.56 3.261(2) 127.6 1_655
C13' H13' O2 0.95 2.31 3.110(2) 141.5 1_655
C16' H16' O1 0.95 2.44 3.381(2) 169.1 2_565
C13 H13 O2' 0.95 2.34 3.123(2) 139.5 2_666
C16 H16 O1' 0.95 2.28 3.216(2) 167.5 1_656
C8' H8A' O3 0.99 2.74 3.502(2) 134.6 2_666
C8 H8A O3' 0.99 2.77 3.521(2) 133.1 2_666
C11 H11 O4 0.95 2.79 3.517(2) 133.5 1_545
C11' H11' O4' 0.95 2.68 3.571(2) 156.2 1_545
C12' H12' N2' 0.95 2.67 3.372(3) 131.1 1_545
C18 H18 O5' 0.95 2.56 3.247(2) 129.3 1_556
C18 H18 O4 0.95 2.37 3.1987(19) 146.1 1_556
C21' H21' N2 0.95 2.66 3.578(12) 161.6 2_576
C20' H20' O5' 0.95 2.54 3.467(13) 165.7 2_676
N1 H1N O2 0.88 1.96 2.6394(18) 133.4 1
N1' H1'N O2' 0.88 1.96 2.6477(19) 134.3 1
C15 H15 N4 0.95 2.74 3.500(3) 137.6 1_655
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_4
O5 S1 O4 O4 0.00(18) . 1
N2 S1 O4 O4 0.00(16) . 1
C4 S1 O4 O4 0.00(15) . 1
C8 N1 C1 C2 -7.6(2) . .
C8 N1 C1 C6 172.32(14) . .
N1 C1 C2 C3 179.94(14) . .
C6 C1 C2 C3 0.0(2) . .
C1 C2 C3 C4 -1.0(2) . .
C1 C2 C3 Cl1 178.03(12) . .
C2 C3 C4 C5 0.9(2) . .
Cl1 C3 C4 C5 -178.12(12) . .
C2 C3 C4 S1 177.67(12) . .
Cl1 C3 C4 S1 -1.35(18) . .
O5 S1 C4 C5 109.08(14) . .
O4 S1 C4 C5 -122.32(13) 1 .
O4 S1 C4 C5 -122.32(13) . .
N2 S1 C4 C5 -7.77(15) . .
O5 S1 C4 C3 -67.53(14) . .
O4 S1 C4 C3 61.08(14) 1 .
O4 S1 C4 C3 61.08(14) . .
N2 S1 C4 C3 175.62(12) . .
C3 C4 C5 C6 0.2(2) . .
S1 C4 C5 C6 -176.52(11) . .
C4 C5 C6 C1 -1.1(2) . .
C4 C5 C6 C7 178.05(15) . .
N1 C1 C6 C5 -178.91(14) . .
C2 C1 C6 C5 1.0(2) . .
N1 C1 C6 C7 1.9(2) . .
C2 C1 C6 C7 -178.20(14) . .
O2 O2 C7 O1 0.0(2) 1 .
O2 O2 C7 C6 0.0(3) 1 .
C5 C6 C7 O2 -176.66(15) . 1
C1 C6 C7 O2 2.5(2) . 1
C5 C6 C7 O2 -176.66(15) . .
C1 C6 C7 O2 2.5(2) . .
C5 C6 C7 O1 2.6(2) . .
C1 C6 C7 O1 -178.26(13) . .
C1 N1 C8 C9 -163.12(14) . .
C12 O3 C9 C10 -0.17(18) . .
C12 O3 C9 C8 177.01(14) . .
N1 C8 C9 C10 99.8(2) . .
N1 C8 C9 O3 -76.54(17) . .
O3 C9 C10 C11 0.1(2) . .
C8 C9 C10 C11 -176.40(18) . .
C9 C10 C11 C12 0.0(2) . .
C10 C11 C12 O3 -0.1(2) . .
C9 O3 C12 C11 0.15(19) . .
C17' N3' C13' C14' 0.2(2) . .
N3' C13' C14' C15' 0.8(3) . .
C13' C14' C15' C16' -1.0(3) . .
C14' C15' C16' C17' 0.3(2) . .
C13' N3' C17' C16' -1.0(2) . .
C13' N3' C17' C17' 178.71(16) . 2_665
C15' C16' C17' N3' 0.7(3) . .
C15' C16' C17' C17' -178.95(17) . 2_665
C17 N3 C13 C14 0.1(2) . .
N3 C13 C14 C15 0.2(3) . .
C13 C14 C15 C16 -0.6(3) . .
C14 C15 C16 C17 0.7(3) . .
C13 N3 C17 C16 -0.1(2) . .
C13 N3 C17 C17 -179.53(17) . 2_767
C15 C16 C17 N3 -0.4(3) . .
C15 C16 C17 C17 179.08(19) . 2_767
C22 N4 C18 C19 -0.1(3) . .
N4 C18 C19 C20' 13.7(5) . .
N4 C18 C19 C20 -11.8(4) . .
C18 C19 C20' C21' -12.1(8) . .
C19 C20' C21' C22 -1.5(10) . .
C18 C19 C20 C21 10.9(7) . .
C19 C20 C21 C22 0.9(9) . .
C18 N4 C22 C21' -14.3(4) . .
C18 N4 C22 C21 12.9(4) . .
C18 N4 C22 C22 -179.3(2) . 2_577
C20' C21' C22 N4 15.2(8) . .
C20' C21' C22 C22 179.5(5) . 2_577
C20 C21 C22 N4 -13.3(7) . .
C20 C21 C22 C22 179.3(5) . 2_577
C8' N1' C1' C2' -9.0(2) . .
C8' N1' C1' C6' 170.97(14) . .
N1' C1' C2' C3' 177.00(14) . .
C6' C1' C2' C3' -3.0(2) . .
C1' C2' C3' C4' -1.5(2) . .
C1' C2' C3' Cl1' 177.04(12) . .
C2' C3' C4' C5' 4.4(2) . .
Cl1' C3' C4' C5' -174.13(12) . .
C2' C3' C4' S1' -179.65(12) . .
Cl1' C3' C4' S1' 1.82(19) . .
O5' S1' C4' C5' -15.26(14) . .
O4' S1' C4' C5' -143.98(12) . .
N2' S1' C4' C5' 99.61(14) . .
O5' S1' C4' C3' 168.80(13) . .
O4' S1' C4' C3' 40.08(15) . .
N2' S1' C4' C3' -76.32(15) . .
C3' C4' C5' C6' -2.7(2) . .
S1' C4' C5' C6' -178.99(11) . .
C4' C5' C6' C1' -1.7(2) . .
C4' C5' C6' C7' 178.09(15) . .
N1' C1' C6' C5' -175.46(14) . .
C2' C1' C6' C5' 4.5(2) . .
N1' C1' C6' C7' 4.8(2) . .
C2' C1' C6' C7' -175.25(14) . .
O2' O2' C7' O1' 0.0(3) 1 .
O2' O2' C7' C6' 0.0(3) 1 .
C5' C6' C7' O2' 179.33(15) . 1
C1' C6' C7' O2' -0.9(2) . 1
C5' C6' C7' O2' 179.33(15) . .
C1' C6' C7' O2' -0.9(2) . .
C5' C6' C7' O1' -1.5(2) . .
C1' C6' C7' O1' 178.24(13) . .
C1' N1' C8' C9' -162.02(14) . .
C12' O3' C9' C10' 0.02(19) . .
C12' O3' C9' C8' 178.99(14) . .
N1' C8' C9' C10' 116.2(2) . .
N1' C8' C9' O3' -62.46(18) . .
O3' C9' C10' C11' -0.2(2) . .
C8' C9' C10' C11' -178.95(18) . .
C9' C10' C11' C12' 0.4(2) . .
C10' C11' C12' O3' -0.4(2) . .
C9' O3' C12' C11' 0.2(2) . .
