#------------------------------------------------------------------------------
#$Date: 2019-11-23 11:39:30 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233127 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/55/7235556.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_7235556
loop_
_publ_author_name
'Jeyalakshmi, Kumaramangalam'
'Selvakumaran, Nagamani'
'Bhuvanesh, Nattamai S. P.'
'Sreekanth, Anantharaman'
'Karvembu, Ramasamy'
_publ_section_title
;
 DNA/protein binding and cytotoxicity studies of copper(ii) complexes
 containing N,N′,N′′-trisubstituted guanidine ligands
;
_journal_issue                   33
_journal_name_full               'RSC Advances'
_journal_page_first              17179
_journal_paper_doi               10.1039/c4ra01459f
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C18 H21 N3 O S'
_chemical_formula_weight         327.44
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0663(16)
_cell_length_b                   10.4930(15)
_cell_length_c                   14.541(2)
_cell_measurement_reflns_used    8437
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.39
_cell_volume                     1688.5(4)
_computing_cell_refinement
; 

  APEX-II(BRUKER-NONIUS, 2003) 

;
_computing_data_collection       'APEX-II (BRUKER-NONIUS, 2003)'
_computing_data_reduction        APEX-II
_computing_molecular_graphics    Olex2
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEX II'
_diffrn_measurement_method       '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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13429
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.9388
_exptl_absorpt_correction_T_min  0.8963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0250
_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)+(0.0367P)²+0.2365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0633
_reflns_number_gt                2886
_reflns_number_total             2952
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra01459f1.cif
_cod_data_source_block           rkb
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/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_sg_symbol_H-M      Pna2(1)
_cod_database_code               7235556
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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 0.07171(7) 0.18366(7) 0.04108(8) 0.0250(2) Uani 0.6879(16) 1 d PD A 1
C1 C 0.20531(12) 0.12064(13) 0.00601(9) 0.0173(3) Uani 0.6879(16) 1 d PD A 1
C2 C 0.2709(3) 0.2129(3) -0.0416(3) 0.0252(10) Uani 0.6879(16) 1 d PD A 1
H2 H 0.3490 0.1969 -0.0661 0.030 Uiso 0.6879(16) 1 calc PR A 1
C3 C 0.2158(4) 0.3257(5) -0.0502(4) 0.0251(4) Uani 0.6879(16) 1 d PD A 1
H3 H 0.2503 0.3959 -0.0820 0.030 Uiso 0.6879(16) 1 calc PR A 1
C4 C 0.1053(5) 0.3302(4) -0.0087(3) 0.0251(4) Uani 0.6879(16) 1 d PD A 1
H4 H 0.0541 0.4029 -0.0073 0.030 Uiso 0.6879(16) 1 calc PR A 1
S1A S 0.2981(2) 0.2100(2) -0.0568(2) 0.0250(2) Uani 0.3121(16) 1 d PD A 2
C1A C 0.20531(12) 0.12064(13) 0.00601(9) 0.0173(3) Uani 0.3121(16) 1 d PD A 2
C2A C 0.1014(7) 0.1881(7) 0.0298(7) 0.0252(10) Uani 0.3121(16) 1 d PD A 2
H2A H 0.0375 0.1519 0.0649 0.030 Uiso 0.3121(16) 1 calc PR A 2
C3A C 0.0995(11) 0.3079(10) -0.0009(7) 0.0251(4) Uani 0.3121(16) 1 d PD A 2
H3A H 0.0338 0.3641 0.0102 0.030 Uiso 0.3121(16) 1 calc PR A 2
C4A C 0.2003(8) 0.3435(12) -0.0499(9) 0.0251(4) Uani 0.3121(16) 1 d PD A 2
H4A H 0.2149 0.4253 -0.0756 0.030 Uiso 0.3121(16) 1 calc PR A 2
O1 O 0.15448(8) -0.07943(9) 0.06730(7) 0.0189(2) Uani 1 1 d . A .
N1 N 0.34908(10) -0.04589(10) 0.00973(8) 0.0152(2) Uani 1 1 d . A .
N2 N 0.34444(10) -0.22501(11) 0.10688(8) 0.0174(2) Uani 1 1 d . A .
H2B H 0.2791 -0.1921 0.1320 0.021 Uiso 1 1 calc R . .
N3 N 0.49785(10) -0.20015(10) 0.00084(8) 0.0162(2) Uani 1 1 d . A .
H3B H 0.5352 -0.2626 0.0295 0.019 Uiso 1 1 calc R . .
C5 C 0.23481(12) -0.01204(12) 0.03045(9) 0.0154(3) Uani 1 1 d . . .
C6 C 0.39401(11) -0.15719(11) 0.03953(9) 0.0139(3) Uani 1 1 d . . .
C7 C 0.38421(13) -0.34731(13) 0.14487(10) 0.0178(3) Uani 1 1 d . . .
H7 H 0.4330 -0.3925 0.0970 0.021 Uiso 1 1 calc R A .
C8 C 0.27396(13) -0.42806(13) 0.16683(11) 0.0222(3) Uani 1 1 d . A .
H8A H 0.2252 -0.4403 0.1104 0.027 Uiso 1 1 calc R . .
H8B H 0.2232 -0.3838 0.2129 0.027 Uiso 1 1 calc R . .
C9 C 0.31312(15) -0.55778(14) 0.20453(11) 0.0265(4) Uani 1 1 d . . .
H9A H 0.2407 -0.6078 0.2216 0.032 Uiso 1 1 calc R A .
H9B H 0.3571 -0.6053 0.1561 0.032 Uiso 1 1 calc R . .
C10 C 0.39385(16) -0.54265(16) 0.28802(11) 0.0308(4) Uani 1 1 d . A .
H10A H 0.4232 -0.6276 0.3075 0.037 Uiso 1 1 calc R . .
H10B H 0.3462 -0.5061 0.3392 0.037 Uiso 1 1 calc R . .
C11 C 0.50155(15) -0.45683(15) 0.26851(12) 0.0297(4) Uani 1 1 d . . .
H11A H 0.5473 -0.4429 0.3262 0.036 Uiso 1 1 calc R A .
H11B H 0.5560 -0.4996 0.2242 0.036 Uiso 1 1 calc R . .
C12 C 0.46275(14) -0.32877(14) 0.22951(11) 0.0245(3) Uani 1 1 d . A .
H12A H 0.4170 -0.2808 0.2767 0.029 Uiso 1 1 calc R . .
H12B H 0.5352 -0.2783 0.2130 0.029 Uiso 1 1 calc R . .
C13 C 0.55259(13) -0.15464(12) -0.08139(9) 0.0153(3) Uani 1 1 d . . .
C14 C 0.67626(13) -0.17425(12) -0.09024(10) 0.0183(3) Uani 1 1 d . A .
H14 H 0.7207 -0.2100 -0.0407 0.022 Uiso 1 1 calc R . .
C15 C 0.73497(14) -0.14178(13) -0.17122(10) 0.0223(3) Uani 1 1 d . . .
H15 H 0.8195 -0.1554 -0.1769 0.027 Uiso 1 1 calc R A .
C16 C 0.67104(15) -0.08982(15) -0.24346(11) 0.0272(3) Uani 1 1 d . A .
H16 H 0.7111 -0.0681 -0.2991 0.033 Uiso 1 1 calc R . .
C17 C 0.54785(15) -0.06959(15) -0.23433(11) 0.0286(4) Uani 1 1 d . . .
H17 H 0.5040 -0.0327 -0.2838 0.034 Uiso 1 1 calc R A .
C18 C 0.48771(14) -0.10245(14) -0.15414(10) 0.0215(3) Uani 1 1 d . A .
H18 H 0.4030 -0.0895 -0.1489 0.026 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
C1 S1 C4 91.89(19)
C2 C1 C5 131.35(19)
C2 C1 S1 109.39(17)
C5 C1 S1 119.24(10)
C3 C2 C1 115.1(3)
C3 C2 H2 122.5
C1 C2 H2 122.5
C2 C3 C4 113.5(6)
C2 C3 H3 123.3
C4 C3 H3 123.3
C3 C4 S1 110.2(5)
C3 C4 H4 124.9
S1 C4 H4 124.9
C3A C2A H2A 123.0
C2A C3A C4A 114.6(14)
C2A C3A H3A 122.7
C4A C3A H3A 122.7
C3A C4A S1A 108.0(13)
C3A C4A H4A 126.0
S1A C4A H4A 126.0
C6 N1 C5 120.34(11)
C6 N2 C7 128.54(11)
C6 N2 H2B 115.7
C7 N2 H2B 115.7
C6 N3 C13 126.70(11)
C6 N3 H3B 116.6
C13 N3 H3B 116.6
O1 C5 N1 127.67(12)
O1 C5 C1 118.56(12)
N1 C5 C1 113.77(11)
N2 C6 N1 123.46(12)
N2 C6 N3 118.51(11)
N1 C6 N3 117.99(12)
N2 C7 C12 111.42(12)
N2 C7 C8 109.06(11)
C12 C7 C8 111.13(12)
N2 C7 H7 108.4
C12 C7 H7 108.4
C8 C7 H7 108.4
C7 C8 C9 110.12(11)
C7 C8 H8A 109.6
C9 C8 H8A 109.6
C7 C8 H8B 109.6
C9 C8 H8B 109.6
H8A C8 H8B 108.2
C10 C9 C8 111.15(13)
C10 C9 H9A 109.4
C8 C9 H9A 109.4
C10 C9 H9B 109.4
C8 C9 H9B 109.4
H9A C9 H9B 108.0
C9 C10 C11 112.00(13)
C9 C10 H10A 109.2
C11 C10 H10A 109.2
C9 C10 H10B 109.2
C11 C10 H10B 109.2
H10A C10 H10B 107.9
C12 C11 C10 111.82(13)
C12 C11 H11A 109.3
C10 C11 H11A 109.3
C12 C11 H11B 109.3
C10 C11 H11B 109.3
H11A C11 H11B 107.9
C7 C12 C11 110.52(13)
C7 C12 H12A 109.5
C11 C12 H12A 109.5
C7 C12 H12B 109.5
C11 C12 H12B 109.5
H12A C12 H12B 108.1
C14 C13 C18 119.75(13)
C14 C13 N3 116.57(12)
C18 C13 N3 123.47(13)
C15 C14 C13 120.22(13)
C15 C14 H14 119.9
C13 C14 H14 119.9
C16 C15 C14 120.23(14)
C16 C15 H15 119.9
C14 C15 H15 119.9
C15 C16 C17 119.48(14)
C15 C16 H16 120.3
C17 C16 H16 120.3
C16 C17 C18 120.98(15)
C16 C17 H17 119.5
C18 C17 H17 119.5
C17 C18 C13 119.34(14)
C17 C18 H18 120.3
C13 C18 H18 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6980(15)
S1 C4 1.740(3)
C1 C2 1.394(4)
C1 C5 1.4734(18)
C2 C3 1.337(6)
C2 H2 0.9500
C3 C4 1.364(4)
C3 H3 0.9500
C4 H4 0.9500
S1A C4A 1.773(8)
C2A C3A 1.335(10)
C2A H2A 0.9500
C3A C4A 1.375(8)
C3A H3A 0.9500
C4A H4A 0.9500
O1 C5 1.2560(16)
N1 C6 1.3413(17)
N1 C5 1.3476(17)
N2 C6 1.3290(18)
N2 C7 1.4648(17)
N2 H2B 0.8800
N3 C6 1.3566(18)
N3 C13 1.4230(18)
N3 H3B 0.8800
C7 C12 1.519(2)
C7 C8 1.519(2)
C7 H7 1.0000
C8 C9 1.530(2)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.516(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.521(2)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.520(2)
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9900
C12 H12B 0.9900
C13 C14 1.390(2)
C13 C18 1.391(2)
C14 C15 1.387(2)
C14 H14 0.9500
C15 C16 1.379(2)
C15 H15 0.9500
C16 C17 1.386(2)
C16 H16 0.9500
C17 C18 1.386(2)
C17 H17 0.9500
C18 H18 0.9500
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
C4 S1 C1 C2 0.4(3)
C4 S1 C1 C5 178.78(19)
C5 C1 C2 C3 -179.1(3)
S1 C1 C2 C3 -1.0(5)
C1 C2 C3 C4 1.2(7)
C2 C3 C4 S1 -0.8(7)
C1 S1 C4 C3 0.2(5)
C2A C3A C4A S1A 1.4(16)
C6 N1 C5 O1 -9.1(2)
C6 N1 C5 C1 170.58(11)
C2 C1 C5 O1 -173.9(3)
S1 C1 C5 O1 8.16(17)
C2 C1 C5 N1 6.4(3)
S1 C1 C5 N1 -171.59(11)
C7 N2 C6 N1 179.56(13)
C7 N2 C6 N3 -2.8(2)
C5 N1 C6 N2 -16.78(19)
C5 N1 C6 N3 165.59(12)
C13 N3 C6 N2 168.08(12)
C13 N3 C6 N1 -14.17(19)
C6 N2 C7 C12 95.10(16)
C6 N2 C7 C8 -141.85(14)
N2 C7 C8 C9 178.65(12)
C12 C7 C8 C9 -58.13(16)
C7 C8 C9 C10 56.18(17)
C8 C9 C10 C11 -54.12(17)
C9 C10 C11 C12 53.51(18)
N2 C7 C12 C11 179.24(12)
C8 C7 C12 C11 57.38(16)
C10 C11 C12 C7 -54.62(17)
C6 N3 C13 C14 155.85(13)
C6 N3 C13 C18 -29.5(2)
C18 C13 C14 C15 0.1(2)
N3 C13 C14 C15 174.98(12)
C13 C14 C15 C16 0.0(2)
C14 C15 C16 C17 0.4(2)
C15 C16 C17 C18 -0.9(2)
C16 C17 C18 C13 1.0(2)
C14 C13 C18 C17 -0.6(2)
N3 C13 C18 C17 -175.11(13)
