Nitric oxide release by N-(2-chloroethyl)-N-nitrosoureas: a rarely discussed mechanistic path towards their anticancer activity
Sarkar, Amrita; Karmakar, Subhendu; Bhattacharyya, Sudipta; Purkait, Kallol; Mukherjee, Arindam; RSC Adv.  (2014) –; doi:10.1039/C4RA11137K

data_7218950
_publ_section_title
;
 Nitric oxide release by N-(2-chloroethyl)-N-nitrosoureas: a rarely
 discussed mechanistic path towards their anticancer activity
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA11137K
_journal_year                    2014
_chemical_formula_moiety         'C12 H14 Cl2 N6 O4'
_chemical_formula_sum            'C12 H14 Cl2 N6 O4'
_chemical_formula_weight         377.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-08-01
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2014-09-19 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                105.678(7)
_cell_angle_beta                 106.754(8)
_cell_angle_gamma                108.541(8)
_cell_formula_units_Z            2
_cell_length_a                   8.9151(8)
_cell_length_b                   9.8682(9)
_cell_length_c                   10.9205(9)
_cell_measurement_reflns_used    2380
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      24.9790
_cell_measurement_theta_min      2.1150
_cell_volume                     799.92(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_details
;
  1 omega   37.00  117.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -       27.3512  178.0000    0.0000 80

  2 omega  -37.00   -5.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -       27.3512  -57.0000   30.0000 32

  3 omega  -46.00   25.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -       27.3512  -57.0000 -180.0000 71

  4 omega  -55.00   70.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -       27.3512  -77.0000  -30.0000 125

  5 omega  -56.00   64.00   1.0000    9.6600
omega____ theta____ kappa____ phi______ frames
    -       27.3512  -77.0000   90.0000 120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0436537000
_diffrn_orient_matrix_UB_12      -0.0651815000
_diffrn_orient_matrix_UB_13      -0.0649221000
_diffrn_orient_matrix_UB_21      0.0727015000
_diffrn_orient_matrix_UB_22      0.0269441000
_diffrn_orient_matrix_UB_23      -0.0161047000
_diffrn_orient_matrix_UB_31      0.0356854000
_diffrn_orient_matrix_UB_32      -0.0431127000
_diffrn_orient_matrix_UB_33      0.0315596000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4599
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.12
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rhombic
_exptl_crystal_F_000             388.0
_exptl_crystal_size_max          .798
_exptl_crystal_size_mid          .587
_exptl_crystal_size_min          .475
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0408
_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/[\s^2^(Fo^2^)+(0.0287P)^2^+0.4718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0940
_reflns_number_gt                2367
_reflns_number_total             2826
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra11137k2.cif
_cod_data_source_block           am_as_pcnuh
_cod_original_cell_volume        799.91(12)
_cod_database_code               7218950
_chemical_oxdiff_formula         C12H14Cl2N6O4
_reflns_odcompleteness_completeness 86.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_check_cif_alert_explanations
;
PLAT430_ALERT_2_B Short Inter D...A Contact O4 .. O4 .. 2.80 Ang.
Comment:Terminal oxygen O4 of one compound is in short contact with O4 of another molecule.
;