#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/81/4508158.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_4508158
loop_
_publ_author_name
'Lee, Jangmi'
'Park, Suzie'
'Yoon, Seon-Joo'
'Jung, Yong Woo'
'Byun, Youngjoo'
'Yuk, Soon Hong'
'Jeon, Min Keyong'
'Kang, Sung Kwon'
'Lee, Eun Hee'
_publ_section_title
;
 Multicomponent System of NPS-1034, an Orally Administered Lung Cancer
 Drug Candidate, with Sulfonic Acids and Solid State Characterization
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3958
_journal_paper_doi               10.1021/cg400651f
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C31 H24 F2 N5 O3, 0.5(C2 H4 O6 S2)'
_chemical_formula_sum            'C32 H26 F2 N5 O6 S'
_chemical_formula_weight         646.64
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.625(2)
_cell_angle_beta                 100.492(5)
_cell_angle_gamma                93.696(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9432(3)
_cell_length_b                   12.1904(4)
_cell_length_c                   18.6492(7)
_cell_measurement_reflns_used    3799
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.22
_cell_measurement_theta_min      2.31
_cell_volume                     1921.31(12)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0724
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            42681
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.15
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             670
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_platon_squeeze_details
;
;
_refine_diff_density_max         1.485
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         9460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0712
_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)+(0.1215P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1916
_refine_ls_wR_factor_ref         0.2118
_reflns_number_gt                5180
_reflns_number_total             9460
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg400651f_si_003.cif
_cod_data_source_block           cnu1056
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4508158
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.2155(3) -0.0585(2) 0.57526(15) 0.0371(6) Uani 1 1 d .
H1 H 0.1096 -0.0749 0.5657 0.045 Uiso 1 1 calc R
C2 C 0.3078(4) -0.1408(3) 0.58842(17) 0.0429(7) Uani 1 1 d .
H2 H 0.2635 -0.2123 0.5879 0.051 Uiso 1 1 calc R
C3 C 0.4659(4) -0.1179(3) 0.60242(18) 0.0467(8) Uani 1 1 d .
H3 H 0.5276 -0.1732 0.6122 0.056 Uiso 1 1 calc R
C4 C 0.5309(3) -0.0132(3) 0.60182(18) 0.0481(8) Uani 1 1 d .
H4 H 0.6368 0.0019 0.6101 0.058 Uiso 1 1 calc R
C5 C 0.4395(3) 0.0701(3) 0.58903(18) 0.0438(7) Uani 1 1 d .
H5 H 0.4845 0.1410 0.5889 0.053 Uiso 1 1 calc R
C6 C 0.2800(3) 0.0486(2) 0.57628(15) 0.0347(6) Uani 1 1 d .
C7 C 0.1854(3) 0.1393(2) 0.56207(16) 0.0357(6) Uani 1 1 d .
C8 C 0.2041(3) 0.2050(2) 0.51435(17) 0.0391(7) Uani 1 1 d .
H8 H 0.2766 0.1976 0.4840 0.047 Uiso 1 1 calc R
N9 N 0.0997(3) 0.2841(2) 0.51754(14) 0.0388(6) Uani 1 1 d .
H9 H 0.0907 0.3333 0.4916 0.047 Uiso 1 1 calc R
C10 C 0.0153(3) 0.2713(2) 0.56760(16) 0.0360(6) Uani 1 1 d .
C11 C 0.0602(3) 0.1801(2) 0.59783(16) 0.0351(6) Uani 1 1 d .
C12 C -0.0113(3) 0.1558(2) 0.65159(17) 0.0410(7) Uani 1 1 d .
C13 C -0.1292(4) 0.2198(3) 0.67377(19) 0.0482(8) Uani 1 1 d .
H13 H -0.1800 0.2034 0.7098 0.058 Uiso 1 1 calc R
C14 C -0.1679(3) 0.3063(3) 0.64162(17) 0.0433(7) Uani 1 1 d .
H14 H -0.2457 0.3481 0.6564 0.052 Uiso 1 1 calc R
N15 N -0.0979(3) 0.3321(2) 0.59022(15) 0.0410(6) Uani 1 1 d .
H15 H -0.102(4) 0.383(3) 0.577(2) 0.054(12) Uiso 1 1 d .
O16 O 0.0359(3) 0.07186(19) 0.68322(12) 0.0534(6) Uani 1 1 d .
C17 C -0.0165(4) 0.0606(3) 0.74744(17) 0.0467(8) Uani 1 1 d .
C19 C -0.0050(4) 0.1325(3) 0.88145(18) 0.0450(7) Uani 1 1 d .
H19 H 0.0347 0.1874 0.9269 0.054 Uiso 1 1 calc R
C20 C -0.1092(3) 0.0432(3) 0.87896(17) 0.0399(7) Uani 1 1 d .
C21 C -0.1641(3) -0.0409(3) 0.80943(17) 0.0420(7) Uani 1 1 d .
H21 H -0.2316 -0.1035 0.8073 0.050 Uiso 1 1 calc R
C18 C 0.0406(4) 0.1399(3) 0.8153(2) 0.0536(9) Uani 1 1 d .
C22 C -0.1170(4) -0.0297(3) 0.74484(19) 0.0468(8) Uani 1 1 d .
H22 H -0.1545 -0.0845 0.6991 0.056 Uiso 1 1 calc R
F23 F 0.1428(3) 0.2230(2) 0.81689(14) 0.0829(7) Uani 1 1 d .
N24 N -0.1549(3) 0.0420(2) 0.94596(14) 0.0426(6) Uani 1 1 d .
H24 H -0.1153 0.0990 0.9840 0.051 Uiso 1 1 calc R
C25 C -0.2531(3) -0.0359(3) 0.96079(16) 0.0392(7) Uani 1 1 d .
O26 O -0.3153(3) -0.1243(2) 0.91443(12) 0.0537(6) Uani 1 1 d .
C27 C -0.2778(3) -0.0020(2) 1.03848(16) 0.0383(7) Uani 1 1 d .
C28 C -0.2117(3) 0.1034(3) 1.09280(17) 0.0400(7) Uani 1 1 d .
N29 N -0.2624(3) 0.1002(2) 1.15855(14) 0.0417(6) Uani 1 1 d .
N30 N -0.3655(3) 0.0036(2) 1.14323(14) 0.0407(6) Uani 1 1 d .
C31 C -0.3693(3) -0.0597(3) 1.07249(17) 0.0389(7) Uani 1 1 d .
O32 O -0.1266(3) 0.18464(19) 1.08785(12) 0.0502(5) Uani 1 1 d .
C33 C -0.4151(4) -0.0327(3) 1.20467(19) 0.0518(8) Uani 1 1 d .
H33A H -0.4541 -0.1121 1.1873 0.078 Uiso 1 1 calc R
H33B H -0.4941 0.0113 1.2208 0.078 Uiso 1 1 calc R
H33C H -0.3298 -0.0211 1.2464 0.078 Uiso 1 1 calc R
C34 C -0.4584(4) -0.1745(3) 1.04124(19) 0.0511(8) Uani 1 1 d .
H34A H -0.4292 -0.2213 1.0747 0.077 Uiso 1 1 calc R
H34B H -0.4377 -0.2093 0.9923 0.077 Uiso 1 1 calc R
H34C H -0.5657 -0.1671 1.0365 0.077 Uiso 1 1 calc R
C35 C -0.2681(3) 0.2004(3) 1.21709(16) 0.0397(7) Uani 1 1 d .
C36 C -0.4050(3) 0.2445(3) 1.22428(17) 0.0466(8) Uani 1 1 d .
H36 H -0.4960 0.2069 1.1923 0.056 Uiso 1 1 calc R
C37 C -0.4058(4) 0.3442(3) 1.27888(18) 0.0504(8) Uani 1 1 d .
H37 H -0.4973 0.3733 1.2858 0.060 Uiso 1 1 calc R
C38 C -0.2703(4) 0.3991(3) 1.32246(17) 0.0479(8) Uani 1 1 d .
C39 C -0.1327(4) 0.3574(3) 1.31766(18) 0.0512(8) Uani 1 1 d .
H39 H -0.0422 0.3964 1.3494 0.061 Uiso 1 1 calc R
C40 C -0.1325(3) 0.2558(3) 1.26420(18) 0.0472(8) Uani 1 1 d .
H40 H -0.0411 0.2248 1.2599 0.057 Uiso 1 1 calc R
F41 F -0.2698(2) 0.50073(17) 1.37434(11) 0.0694(6) Uani 1 1 d .
C42 C 0.4696(3) 0.4381(2) 0.48115(16) 0.0352(6) Uani 1 1 d .
H42A H 0.4489 0.4012 0.5193 0.042 Uiso 1 1 calc R
H42B H 0.5469 0.3998 0.4574 0.042 Uiso 1 1 calc R
S43 S 0.29898(7) 0.42361(6) 0.41162(4) 0.0341(2) Uani 1 1 d .
O44 O 0.18467(19) 0.47555(16) 0.45358(11) 0.0366(5) Uani 1 1 d .
O45 O 0.2576(2) 0.30264(17) 0.37829(12) 0.0455(5) Uani 1 1 d .
O46 O 0.3347(2) 0.48658(17) 0.35971(11) 0.0434(5) Uani 1 1 d .
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'
F F 0.0171 0.0103 '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
C2 C1 C6 120.3(3) .
C2 C1 H1 119.8 .
C6 C1 H1 119.8 .
C1 C2 C3 120.5(3) .
C1 C2 H2 119.7 .
C3 C2 H2 119.7 .
C4 C3 C2 119.6(3) .
C4 C3 H3 120.2 .
C2 C3 H3 120.2 .
C3 C4 C5 120.3(3) .
C3 C4 H4 119.9 .
C5 C4 H4 119.9 .
C4 C5 C6 120.6(3) .
C4 C5 H5 119.7 .
C6 C5 H5 119.7 .
C1 C6 C5 118.6(2) .
C1 C6 C7 122.1(2) .
C5 C6 C7 119.2(3) .
C8 C7 C11 106.2(2) .
C8 C7 C6 125.9(3) .
C11 C7 C6 127.8(3) .
C7 C8 N9 110.3(3) .
C7 C8 H8 124.9 .
N9 C8 H8 124.9 .
C10 N9 C8 108.6(2) .
C10 N9 H9 125.7 .
C8 N9 H9 125.7 .
N9 C10 N15 128.9(3) .
N9 C10 C11 109.8(2) .
N15 C10 C11 121.2(3) .
C12 C11 C10 118.3(2) .
C12 C11 C7 136.5(2) .
C10 C11 C7 105.1(2) .
O16 C12 C11 118.6(2) .
O16 C12 C13 122.0(3) .
C11 C12 C13 119.3(3) .
C14 C13 C12 119.3(3) .
C14 C13 H13 120.4 .
C12 C13 H13 120.4 .
N15 C14 C13 122.1(3) .
N15 C14 H14 119.0 .
C13 C14 H14 119.0 .
C14 N15 C10 119.7(3) .
C14 N15 H15 127(3) .
C10 N15 H15 112(3) .
C12 O16 C17 118.7(2) .
C22 C17 C18 119.5(3) .
C22 C17 O16 121.6(3) .
C18 C17 O16 118.9(3) .
C20 C19 C18 119.2(3) .
C20 C19 H19 120.4 .
C18 C19 H19 120.4 .
C19 C20 N24 116.9(3) .
C19 C20 C21 119.1(3) .
N24 C20 C21 124.0(3) .
C22 C21 C20 119.8(3) .
C22 C21 H21 120.1 .
C20 C21 H21 120.1 .
F23 C18 C17 118.2(3) .
F23 C18 C19 120.1(3) .
C17 C18 C19 121.7(3) .
C17 C22 C21 120.7(3) .
C17 C22 H22 119.7 .
C21 C22 H22 119.7 .
C25 N24 C20 129.9(3) .
C25 N24 H24 115.0 .
C20 N24 H24 115.0 .
O26 C25 N24 124.1(3) .
O26 C25 C27 123.1(3) .
N24 C25 C27 112.8(3) .
C31 C27 C28 107.5(3) .
C31 C27 C25 128.3(3) .
C28 C27 C25 124.2(3) .
O32 C28 N29 123.4(3) .
O32 C28 C27 131.3(3) .
N29 C28 C27 105.3(3) .
N30 N29 C28 108.8(2) .
N30 N29 C35 121.8(2) .
C28 N29 C35 123.1(3) .
C31 N30 N29 108.8(2) .
C31 N30 C33 127.9(3) .
N29 N30 C33 120.5(2) .
N30 C31 C27 109.2(3) .
N30 C31 C34 122.1(3) .
C27 C31 C34 128.7(3) .
N30 C33 H33A 109.5 .
N30 C33 H33B 109.5 .
H33A C33 H33B 109.5 .
N30 C33 H33C 109.5 .
H33A C33 H33C 109.5 .
H33B C33 H33C 109.5 .
C31 C34 H34A 109.5 .
C31 C34 H34B 109.5 .
H34A C34 H34B 109.5 .
C31 C34 H34C 109.5 .
H34A C34 H34C 109.5 .
H34B C34 H34C 109.5 .
C40 C35 C36 120.5(3) .
C40 C35 N29 118.4(3) .
C36 C35 N29 121.0(3) .
C37 C36 C35 119.7(3) .
C37 C36 H36 120.2 .
C35 C36 H36 120.2 .
C38 C37 C36 118.6(3) .
C38 C37 H37 120.7 .
C36 C37 H37 120.7 .
C37 C38 F41 118.8(3) .
C37 C38 C39 123.4(3) .
F41 C38 C39 117.8(3) .
C38 C39 C40 118.0(3) .
C38 C39 H39 121.0 .
C40 C39 H39 121.0 .
C39 C40 C35 119.9(3) .
C39 C40 H40 120.1 .
C35 C40 H40 120.1 .
C42 C42 S43 111.9(2) 2_666
C42 C42 H42A 109.2 2_666
S43 C42 H42A 109.2 .
C42 C42 H42B 109.2 2_666
S43 C42 H42B 109.2 .
H42A C42 H42B 107.9 .
O45 S43 O46 114.66(13) .
O45 S43 O44 111.92(12) .
O46 S43 O44 111.53(11) .
O45 S43 C42 106.09(12) .
O46 S43 C42 106.41(13) .
O44 S43 C42 105.48(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.381(4) .
C1 C6 1.387(4) .
C1 H1 0.9300 .
C2 C3 1.387(4) .
C2 H2 0.9300 .
C3 C4 1.372(4) .
C3 H3 0.9300 .
C4 C5 1.383(4) .
C4 H4 0.9300 .
C5 C6 1.398(4) .
C5 H5 0.9300 .
C6 C7 1.481(4) .
C7 C8 1.363(4) .
C7 C11 1.457(4) .
C8 N9 1.383(3) .
C8 H8 0.9300 .
N9 C10 1.334(4) .
N9 H9 0.8600 .
C10 N15 1.359(4) .
C10 C11 1.416(4) .
C11 C12 1.364(4) .
C12 O16 1.357(3) .
C12 C13 1.412(4) .
C13 C14 1.372(4) .
C13 H13 0.9300 .
C14 N15 1.325(4) .
C14 H14 0.9300 .
N15 H15 0.73(3) .
O16 C17 1.397(4) .
C17 C22 1.361(5) .
C17 C18 1.371(5) .
C19 C20 1.372(4) .
C19 C18 1.390(5) .
C19 H19 0.9300 .
C20 N24 1.387(4) .
C20 C21 1.416(4) .
C21 C22 1.381(4) .
C21 H21 0.9300 .
C18 F23 1.311(4) .
C22 H22 0.9300 .
N24 C25 1.364(4) .
N24 H24 0.8600 .
C25 O26 1.223(4) .
C25 C27 1.465(4) .
C27 C31 1.381(4) .
C27 C28 1.433(4) .
C28 O32 1.242(4) .
C28 N29 1.391(4) .
N29 N30 1.383(3) .
N29 C35 1.428(4) .
N30 C31 1.343(4) .
N30 C33 1.457(4) .
C31 C34 1.486(4) .
C33 H33A 0.9600 .
C33 H33B 0.9600 .
C33 H33C 0.9600 .
C34 H34A 0.9600 .
C34 H34B 0.9600 .
C34 H34C 0.9600 .
C35 C40 1.381(4) .
C35 C36 1.384(4) .
C36 C37 1.376(4) .
C36 H36 0.9300 .
C37 C38 1.356(4) .
C37 H37 0.9300 .
C38 F41 1.365(3) .
C38 C39 1.371(4) .
C39 C40 1.380(4) .
C39 H39 0.9300 .
C40 H40 0.9300 .
C42 C42 1.512(5) 2_666
C42 S43 1.780(3) .
C42 H42A 0.9700 .
C42 H42B 0.9700 .
S43 O45 1.443(2) .
S43 O46 1.444(2) .
S43 O44 1.4775(18) .
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
N9 H9 O44 0.86 2.21 2.992(3) 152.0 .
N15 H15 O44 0.73(3) 2.08(4) 2.782(3) 162(4) 2_566
N24 H24 O32 0.86 1.98 2.733(3) 145.7 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.031 0.500 0.000 554 162 ' '
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146604
