#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:12:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180293 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/07/7150725.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_7150725
loop_
_publ_author_name
'Sivappa, Rasapalli'
'Mukherjee, Sabuj'
'Dias, H. V. Rasika'
'Lovely, Carl J.'
_publ_section_title
;
 Studies toward the total synthesis of the oroidin dimers
;
_journal_issue                   16
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3215
_journal_page_last               3218
_journal_paper_doi               10.1039/b909482b
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C21 H23 N5 O5 S'
_chemical_formula_weight         457.50
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 115.389(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6504(12)
_cell_length_b                   19.300(2)
_cell_length_c                   11.4094(13)
_cell_measurement_reflns_used    5435
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.24
_cell_volume                     2118.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0794
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13950
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.143
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0508
_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)+(0.0837P)²+0.1677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1468
_reflns_number_gt                4030
_reflns_number_total             5092
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b909482b.txt
_cod_data_source_block           sabuj1m
_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 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7150725
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'
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
S1 S 0.02092(4) 0.20576(2) 0.29900(4) 0.02053(14) Uani 1 1 d . . .
O1 O 0.10131(13) -0.12717(7) 0.23534(14) 0.0296(3) Uani 1 1 d . . .
O2 O 0.08456(14) -0.03443(7) 0.34265(15) 0.0327(3) Uani 1 1 d . . .
O3 O 0.52154(13) 0.05266(7) 0.14989(14) 0.0294(3) Uani 1 1 d . . .
O4 O 0.06584(14) 0.25666(7) 0.39927(14) 0.0297(3) Uani 1 1 d . . .
O5 O -0.02642(14) 0.22420(7) 0.16599(13) 0.0291(3) Uani 1 1 d . . .
N1 N 0.36152(15) 0.10148(8) 0.45030(15) 0.0242(3) Uani 1 1 d . . .
N2 N 0.16414(14) 0.15682(7) 0.33299(14) 0.0187(3) Uani 1 1 d . . .
N3 N -0.09311(15) 0.15704(8) 0.31294(15) 0.0225(3) Uani 1 1 d . . .
N4 N 0.17959(14) -0.01030(7) 0.07522(14) 0.0197(3) Uani 1 1 d . . .
N5 N 0.29264(15) 0.06240(8) -0.00343(15) 0.0223(3) Uani 1 1 d . . .
C1 C 0.15623(19) -0.07112(10) 0.31140(18) 0.0250(4) Uani 1 1 d . . .
C2 C 0.20349(19) -0.16310(10) 0.2059(2) 0.0291(4) Uani 1 1 d . . .
H2A H 0.1731 -0.1648 0.1109 0.035 Uiso 1 1 calc R . .
H2B H 0.2154 -0.2112 0.2393 0.035 Uiso 1 1 calc R . .
C3 C 0.34106(18) -0.12310(9) 0.27149(18) 0.0228(4) Uani 1 1 d . . .
H3 H 0.4166 -0.1541 0.3312 0.027 Uiso 1 1 calc R . .
C4 C 0.38731(18) -0.08583(9) 0.17713(18) 0.0223(4) Uani 1 1 d . . .
H4A H 0.4899 -0.0850 0.2121 0.027 Uiso 1 1 calc R . .
H4B H 0.3488 -0.1092 0.0916 0.027 Uiso 1 1 calc R . .
C5 C 0.32918(16) -0.01188(9) 0.16508(17) 0.0191(4) Uani 1 1 d . . .
C6 C 0.39893(17) 0.03788(9) 0.10836(18) 0.0210(4) Uani 1 1 d . . .
C7 C 0.16848(18) 0.03157(9) -0.01537(17) 0.0203(4) Uani 1 1 d . . .
H7 H 0.0817 0.0412 -0.0863 0.024 Uiso 1 1 calc R . .
C8 C 0.35477(16) 0.00370(8) 0.30607(16) 0.0186(3) Uani 1 1 d . . .
H8 H 0.4577 0.0076 0.3574 0.022 Uiso 1 1 calc R . .
C9 C 0.31037(17) -0.06539(9) 0.34828(17) 0.0212(4) Uani 1 1 d . . .
H9 H 0.3650 -0.0729 0.4436 0.025 Uiso 1 1 calc R . .
C10 C 0.29366(17) 0.06843(9) 0.33094(17) 0.0190(3) Uani 1 1 d . . .
C11 C 0.17213(17) 0.10152(9) 0.25778(17) 0.0201(4) Uani 1 1 d . . .
H11 H 0.1062 0.0894 0.1729 0.024 Uiso 1 1 calc R . .
C12 C 0.28114(18) 0.15337(10) 0.44889(18) 0.0240(4) Uani 1 1 d . . .
H12 H 0.3012 0.1846 0.5190 0.029 Uiso 1 1 calc R . .
C13 C 0.3104(2) 0.10956(10) -0.09506(19) 0.0263(4) Uani 1 1 d . . .
H13A H 0.2852 0.0849 -0.1782 0.032 Uiso 1 1 calc R . .
H13B H 0.4097 0.1226 -0.0609 0.032 Uiso 1 1 calc R . .
C14 C 0.22443(18) 0.17477(9) -0.12101(18) 0.0222(4) Uani 1 1 d . . .
C15 C 0.1792(2) 0.20640(9) -0.24182(19) 0.0257(4) Uani 1 1 d . . .
H15 H 0.2026 0.1866 -0.3061 0.031 Uiso 1 1 calc R . .
C16 C 0.1001(2) 0.26661(10) -0.2696(2) 0.0296(4) Uani 1 1 d . . .
H16 H 0.0706 0.2880 -0.3521 0.036 Uiso 1 1 calc R . .
C17 C 0.0645(2) 0.29538(10) -0.1770(2) 0.0297(4) Uani 1 1 d . . .
H17 H 0.0104 0.3365 -0.1958 0.036 Uiso 1 1 calc R . .
C18 C 0.1082(2) 0.26387(10) -0.0566(2) 0.0291(4) Uani 1 1 d . . .
H18 H 0.0828 0.2832 0.0067 0.035 Uiso 1 1 calc R . .
C19 C 0.1885(2) 0.20436(9) -0.02817(19) 0.0254(4) Uani 1 1 d . . .
H19 H 0.2193 0.1836 0.0551 0.030 Uiso 1 1 calc R . .
C20 C -0.1605(2) 0.10372(11) 0.2135(2) 0.0325(5) Uani 1 1 d . . .
H20A H -0.1050 0.0611 0.2377 0.049 Uiso 1 1 calc R . .
H20B H -0.1676 0.1202 0.1296 0.049 Uiso 1 1 calc R . .
H20C H -0.2537 0.0942 0.2068 0.049 Uiso 1 1 calc R . .
C21 C -0.0710(2) 0.13577(13) 0.4436(2) 0.0399(5) Uani 1 1 d . . .
H21A H -0.1570 0.1158 0.4404 0.060 Uiso 1 1 calc R . .
H21B H -0.0445 0.1762 0.5011 0.060 Uiso 1 1 calc R . .
H21C H 0.0032 0.1011 0.4765 0.060 Uiso 1 1 calc R . .
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'
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
O5 S1 O4 121.77(9) . . ?
O5 S1 N3 108.45(8) . . ?
O4 S1 N3 109.48(8) . . ?
O5 S1 N2 104.86(8) . . ?
O4 S1 N2 103.96(8) . . ?
N3 S1 N2 107.34(8) . . ?
C1 O1 C2 111.77(14) . . ?
C12 N1 C10 105.96(14) . . ?
C12 N2 C11 106.58(14) . . ?
C12 N2 S1 127.12(12) . . ?
C11 N2 S1 124.96(12) . . ?
C21 N3 C20 113.67(17) . . ?
C21 N3 S1 117.99(13) . . ?
C20 N3 S1 118.38(13) . . ?
C7 N4 C5 105.81(14) . . ?
C6 N5 C7 108.11(14) . . ?
C6 N5 C13 124.83(15) . . ?
C7 N5 C13 126.99(15) . . ?
O2 C1 O1 120.43(17) . . ?
O2 C1 C9 128.71(18) . . ?
O1 C1 C9 110.84(15) . . ?
O1 C2 C3 107.55(15) . . ?
O1 C2 H2A 110.2 . . ?
C3 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
C3 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
C9 C3 C2 104.48(14) . . ?
C9 C3 C4 105.66(14) . . ?
C2 C3 C4 114.72(15) . . ?
C9 C3 H3 110.6 . . ?
C2 C3 H3 110.6 . . ?
C4 C3 H3 110.6 . . ?
C5 C4 C3 104.99(14) . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4B 110.7 . . ?
C3 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
N4 C5 C6 105.65(14) . . ?
N4 C5 C4 110.71(14) . . ?
C6 C5 C4 111.92(14) . . ?
N4 C5 C8 112.03(13) . . ?
C6 C5 C8 114.93(14) . . ?
C4 C5 C8 101.73(14) . . ?
O3 C6 N5 126.81(17) . . ?
O3 C6 C5 128.45(16) . . ?
N5 C6 C5 104.72(14) . . ?
N4 C7 N5 115.69(15) . . ?
N4 C7 H7 122.2 . . ?
N5 C7 H7 122.2 . . ?
C10 C8 C5 117.75(14) . . ?
C10 C8 C9 116.30(14) . . ?
C5 C8 C9 102.37(13) . . ?
C10 C8 H8 106.5 . . ?
C5 C8 H8 106.5 . . ?
C9 C8 H8 106.5 . . ?
C1 C9 C3 105.01(14) . . ?
C1 C9 C8 114.40(14) . . ?
C3 C9 C8 106.09(14) . . ?
C1 C9 H9 110.4 . . ?
C3 C9 H9 110.4 . . ?
C8 C9 H9 110.4 . . ?
C11 C10 N1 110.06(15) . . ?
C11 C10 C8 130.87(16) . . ?
N1 C10 C8 118.94(15) . . ?
C10 C11 N2 105.94(15) . . ?
C10 C11 H11 127.0 . . ?
N2 C11 H11 127.0 . . ?
N1 C12 N2 111.45(15) . . ?
N1 C12 H12 124.3 . . ?
N2 C12 H12 124.3 . . ?
N5 C13 C14 114.03(14) . . ?
N5 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
N5 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C19 118.80(17) . . ?
C15 C14 C13 118.93(16) . . ?
C19 C14 C13 122.26(16) . . ?
C16 C15 C14 120.76(18) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 119.99(18) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.67(18) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 120.44(18) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C14 120.34(17) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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
S1 O5 1.4240(14) . ?
S1 O4 1.4260(14) . ?
S1 N3 1.5969(15) . ?
S1 N2 1.6917(14) . ?
O1 C1 1.353(2) . ?
O1 C2 1.446(2) . ?
O2 C1 1.202(2) . ?
O3 C6 1.217(2) . ?
N1 C12 1.313(2) . ?
N1 C10 1.393(2) . ?
N2 C12 1.376(2) . ?
N2 C11 1.395(2) . ?
N3 C21 1.464(3) . ?
N3 C20 1.471(2) . ?
N4 C7 1.277(2) . ?
N4 C5 1.480(2) . ?
N5 C6 1.376(2) . ?
N5 C7 1.402(2) . ?
N5 C13 1.458(2) . ?
C1 C9 1.514(2) . ?
C2 C3 1.537(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C9 1.536(2) . ?
C3 C4 1.541(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.538(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.518(2) . ?
C5 C8 1.542(2) . ?
C7 H7 0.9500 . ?
C8 C10 1.491(2) . ?
C8 C9 1.558(2) . ?
C8 H8 1.0000 . ?
C9 H9 1.0000 . ?
C10 C11 1.361(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.509(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.391(3) . ?
C14 C19 1.394(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
