#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:43:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180516 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/85/7218573.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_7218573
loop_
_publ_author_name
'Sirajuddin, Muhammad -'
'Ali, Saqib'
'McKee, Vickie'
'Zaib, Sumera'
'Iqbal, Jamshed'
_publ_section_title
;
 Organotin(IV) carboxylate derivatives as a new addition to anticancer and
 antileishmanial agents: Design, physicochemical characterization and
 interaction with Salmon sperm DNA
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA10487K
_journal_year                    2014
_chemical_formula_sum            'C23 H38 N2 O6 Sn'
_chemical_formula_weight         557.24
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 98.974(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.853(3)
_cell_length_b                   10.0376(18)
_cell_length_c                   16.700(3)
_cell_measurement_temperature    150(2)
_cell_volume                     2624.9(8)
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35017
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.264
_diffrn_reflns_theta_min         2.375
_exptl_absorpt_coefficient_mu    1.011
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.541
_refine_diff_density_min         -2.074
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         6473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0611P)²+7.4715P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1894
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3154
_reflns_number_total             6473
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ra10487k1.cif
_cod_data_source_block           SAD
_cod_original_cell_volume        2624.8(8)
_cod_database_code               7218573
#BEGIN Tags that were not found in dictionaries:
_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   0.654
_shelx_estimated_absorpt_t_max   0.942
_shelxl_version_number           2012-9
#END Tags that were not found in dictionaries
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'
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
Sn1 Sn 0.04397(3) 0.16841(5) 0.27827(4) 0.0629(2) Uani 1 1 d . .
O1 O -0.0408(3) -0.0205(4) 0.2409(4) 0.0678(16) Uani 1 1 d . .
C1 C -0.1128(4) -0.0493(7) 0.2017(5) 0.0547(19) Uani 1 1 d . .
O2 O -0.1359(3) -0.1676(4) 0.1861(4) 0.0699(15) Uani 1 1 d . .
C2 C -0.1753(4) 0.0596(6) 0.1718(5) 0.0527(17) Uani 1 1 d . .
H2A H -0.1554 0.1064 0.1260 0.063 Uiso 1 1 calc R U
H2B H -0.1769 0.1251 0.2158 0.063 Uiso 1 1 calc R U
C3 C -0.2653(4) 0.0065(7) 0.1440(4) 0.0527(17) Uani 1 1 d . .
H3A H -0.3029 0.0801 0.1207 0.063 Uiso 1 1 calc R U
H3B H -0.2640 -0.0615 0.1012 0.063 Uiso 1 1 calc R U
C4 C -0.3010(4) -0.0550(6) 0.2150(4) 0.0451(15) Uani 1 1 d . .
O3 O -0.2808(3) -0.0155(5) 0.2848(3) 0.0571(12) Uani 1 1 d . .
N1 N -0.3580(3) -0.1548(5) 0.1948(3) 0.0432(12) Uani 1 1 d . .
H1 H -0.3710 -0.1733 0.1428 0.052 Uiso 1 1 calc R U
C5 C -0.3990(4) -0.2322(6) 0.2479(4) 0.0413(15) Uani 1 1 d . .
C6 C -0.3777(4) -0.2314(7) 0.3315(4) 0.0462(15) Uani 1 1 d . .
H6 H -0.3346 -0.1733 0.3576 0.055 Uiso 1 1 calc R U
C7 C -0.4200(4) -0.3162(7) 0.3760(4) 0.0462(16) Uani 1 1 d . .
C8 C -0.4830(4) -0.4013(7) 0.3433(4) 0.0554(18) Uani 1 1 d . .
H8 H -0.5098 -0.4596 0.3765 0.067 Uiso 1 1 calc R U
C9 C -0.5067(4) -0.3996(7) 0.2599(4) 0.0539(18) Uani 1 1 d . .
H9 H -0.5513 -0.4561 0.2351 0.065 Uiso 1 1 calc R U
C10 C -0.4658(4) -0.3162(7) 0.2126(4) 0.0467(16) Uani 1 1 d . .
N2 N -0.3964(4) -0.3124(8) 0.4648(4) 0.0701(19) Uani 1 1 d . .
O5 O -0.3526(4) -0.2214(7) 0.4963(3) 0.0864(19) Uani 1 1 d . .
O6 O -0.4217(4) -0.4018(7) 0.5049(3) 0.090(2) Uani 1 1 d . .
O4 O -0.4841(3) -0.3070(5) 0.1302(3) 0.0574(13) Uani 1 1 d . .
C11 C -0.5496(6) -0.3931(11) 0.0891(5) 0.092(3) Uani 1 1 d . .
H11A H -0.5334 -0.4863 0.1003 0.138 Uiso 1 1 calc R U
H11B H -0.5564 -0.3768 0.0306 0.138 Uiso 1 1 calc R U
H11C H -0.6037 -0.3748 0.1086 0.138 Uiso 1 1 calc R U
C12 C 0.1339(5) 0.0327(9) 0.3428(8) 0.129(5) Uani 1 1 d . .
H12A H 0.1403 0.0569 0.4009 0.155 Uiso 1 1 calc R U
H12B H 0.1076 -0.0570 0.3374 0.155 Uiso 1 1 calc R U
C13 C 0.2164(5) 0.0208(11) 0.3229(7) 0.104(4) Uani 1 1 d . .
H13A H 0.2433 0.1100 0.3288 0.125 Uiso 1 1 calc R U
H13B H 0.2104 -0.0032 0.2648 0.125 Uiso 1 1 calc R U
C14 C 0.2785(5) -0.0775(10) 0.3697(7) 0.097(3) Uani 1 1 d . .
H14A H 0.3054 -0.0348 0.4208 0.117 Uiso 1 1 calc R U
H14B H 0.2459 -0.1556 0.3843 0.117 Uiso 1 1 calc R U
C15 C 0.3431(8) -0.1223(13) 0.3278(11) 0.177(7) Uani 1 1 d . .
H15A H 0.3180 -0.1480 0.2726 0.266 Uiso 1 1 calc R U
H15B H 0.3717 -0.1995 0.3560 0.266 Uiso 1 1 calc R U
H15C H 0.3847 -0.0508 0.3256 0.266 Uiso 1 1 calc R U
C16 C -0.0477(5) 0.2431(8) 0.3461(5) 0.070(2) Uani 1 1 d . .
H16A H -0.0213 0.3175 0.3801 0.084 Uiso 1 1 calc R U
H16B H -0.0957 0.2807 0.3077 0.084 Uiso 1 1 calc R U
C17 C -0.0840(7) 0.1450(11) 0.4006(6) 0.101(3) Uani 1 1 d . .
H17A H -0.0360 0.0998 0.4352 0.122 Uiso 1 1 calc R U
H17B H -0.1167 0.0762 0.3664 0.122 Uiso 1 1 calc R U
C18 C -0.1419(12) 0.2071(17) 0.4550(8) 0.170(8) Uani 1 1 d . .
H18A H -0.1546 0.1394 0.4947 0.204 Uiso 1 1 calc R U
H18B H -0.1110 0.2812 0.4859 0.204 Uiso 1 1 calc R U
C19 C -0.2211(9) 0.2570(19) 0.4122(10) 0.186(9) Uani 1 1 d . .
H19A H -0.2099 0.3346 0.3798 0.279 Uiso 1 1 calc R U
H19B H -0.2584 0.2831 0.4511 0.279 Uiso 1 1 calc R U
H19C H -0.2491 0.1875 0.3763 0.279 Uiso 1 1 calc R U
C20 C 0.0427(6) 0.1972(8) 0.1547(6) 0.087(3) Uani 1 1 d . .
H20A H 0.0253 0.1127 0.1262 0.104 Uiso 1 1 calc R U
H20B H -0.0013 0.2647 0.1354 0.104 Uiso 1 1 calc R U
C21 C 0.1269(11) 0.2417(18) 0.1308(12) 0.201(9) Uani 1 1 d . .
H21A H 0.1379 0.3326 0.1530 0.241 Uiso 1 1 calc R U
H21B H 0.1716 0.1837 0.1608 0.241 Uiso 1 1 calc R U
C22 C 0.1420(11) 0.246(2) 0.0532(10) 0.201(9) Uani 1 1 d . .
H22A H 0.1976 0.2892 0.0504 0.242 Uiso 1 1 calc R U
H22B H 0.0965 0.2965 0.0188 0.242 Uiso 1 1 calc R U
C23 C 0.1430(12) 0.1099(18) 0.0266(10) 0.208(9) Uani 1 1 d . .
H23A H 0.2013 0.0747 0.0389 0.313 Uiso 1 1 calc R U
H23B H 0.1236 0.1057 -0.0320 0.313 Uiso 1 1 calc R U
H23C H 0.1050 0.0566 0.0547 0.313 Uiso 1 1 calc R 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'
Sn Sn -0.6537 1.4246 '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
C20 Sn1 C16 125.5(4) . .
C20 Sn1 C12 119.4(5) . .
C16 Sn1 C12 114.6(4) . .
C20 Sn1 O2 93.9(3) . 2
C16 Sn1 O2 94.0(3) . 2
C12 Sn1 O2 88.8(3) . 2
C20 Sn1 O1 86.1(3) . .
C16 Sn1 O1 90.9(2) . .
C12 Sn1 O1 85.9(3) . .
O2 Sn1 O1 173.90(15) 2 .
C1 O1 Sn1 139.3(4) . .
O1 C1 O2 122.5(6) . .
O1 C1 C2 120.2(6) . .
O2 C1 C2 117.4(6) . .
C1 O2 Sn1 119.1(4) . 2_545
C1 C2 C3 112.5(5) . .
C4 C3 C2 110.3(6) . .
O3 C4 N1 122.8(6) . .
O3 C4 C3 122.4(6) . .
N1 C4 C3 114.8(6) . .
C4 N1 C5 127.1(5) . .
C6 C5 C10 118.3(6) . .
C6 C5 N1 124.6(6) . .
C10 C5 N1 117.1(6) . .
C7 C6 C5 118.7(6) . .
C8 C7 C6 124.2(6) . .
C8 C7 N2 118.3(6) . .
C6 C7 N2 117.4(6) . .
C7 C8 C9 117.5(6) . .
C10 C9 C8 120.4(6) . .
O4 C10 C9 125.0(6) . .
O4 C10 C5 114.2(6) . .
C9 C10 C5 120.8(6) . .
O5 N2 O6 121.8(7) . .
O5 N2 C7 119.6(7) . .
O6 N2 C7 118.6(7) . .
C10 O4 C11 117.6(6) . .
C13 C12 Sn1 120.5(8) . .
C12 C13 C14 119.1(9) . .
C15 C14 C13 114.6(11) . .
C17 C16 Sn1 116.7(7) . .
C16 C17 C18 114.5(10) . .
C19 C18 C17 114.0(12) . .
C21 C20 Sn1 115.4(10) . .
C22 C21 C20 123.7(16) . .
C21 C22 C23 106.2(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn1 C20 2.081(10) .
Sn1 C16 2.114(8) .
Sn1 C12 2.138(8) .
Sn1 O2 2.217(5) 2
Sn1 O1 2.351(5) .
O1 C1 1.257(8) .
C1 O2 1.258(8) .
C1 C2 1.508(9) .
O2 Sn1 2.218(5) 2_545
C2 C3 1.526(9) .
C3 C4 1.522(9) .
C4 O3 1.225(8) .
C4 N1 1.357(8) .
N1 C5 1.411(8) .
C5 C6 1.384(9) .
C5 C10 1.410(8) .
C6 C7 1.371(9) .
C7 C8 1.363(9) .
C7 N2 1.472(9) .
C8 C9 1.385(9) .
C9 C10 1.379(9) .
C10 O4 1.365(8) .
N2 O5 1.217(8) .
N2 O6 1.225(8) .
O4 C11 1.440(9) .
C12 C13 1.405(12) .
C13 C14 1.521(11) .
C14 C15 1.401(14) .
C16 C17 1.515(11) .
C17 C18 1.523(17) .
C18 C19 1.43(2) .
C20 C21 1.519(14) .
C21 C22 1.354(19) .
C22 C23 1.44(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 H1 O6 0.88 2.44 3.225(8) 149.1 4
C6 H6 O3 0.95 2.24 2.835(8) 119.5 .
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_4
Sn1 O1 C1 O2 172.4(5) .
Sn1 O1 C1 C2 -7.8(12) .
O1 C1 O2 Sn1 -4.0(10) 2_545
C2 C1 O2 Sn1 176.2(5) 2_545
O1 C1 C2 C3 -166.2(7) .
O2 C1 C2 C3 13.5(10) .
C1 C2 C3 C4 63.9(8) .
C2 C3 C4 O3 30.5(8) .
C2 C3 C4 N1 -150.8(5) .
O3 C4 N1 C5 -3.5(10) .
C3 C4 N1 C5 177.8(5) .
C4 N1 C5 C6 -10.0(10) .
C4 N1 C5 C10 170.3(6) .
C10 C5 C6 C7 2.7(9) .
N1 C5 C6 C7 -177.0(6) .
C5 C6 C7 C8 -0.8(10) .
C5 C6 C7 N2 -179.6(6) .
C6 C7 C8 C9 -1.3(11) .
N2 C7 C8 C9 177.5(6) .
C7 C8 C9 C10 1.4(11) .
C8 C9 C10 O4 179.9(7) .
C8 C9 C10 C5 0.6(10) .
C6 C5 C10 O4 178.0(6) .
N1 C5 C10 O4 -2.3(8) .
C6 C5 C10 C9 -2.6(9) .
N1 C5 C10 C9 177.1(6) .
C8 C7 N2 O5 -166.2(7) .
C6 C7 N2 O5 12.7(10) .
C8 C7 N2 O6 13.8(10) .
C6 C7 N2 O6 -167.3(7) .
C9 C10 O4 C11 -1.5(10) .
C5 C10 O4 C11 177.8(7) .
Sn1 C12 C13 C14 -179.6(8) .
C12 C13 C14 C15 155.5(12) .
Sn1 C16 C17 C18 173.4(9) .
C16 C17 C18 C19 68.0(15) .
Sn1 C20 C21 C22 169.6(17) .
C20 C21 C22 C23 -68(2) .
