The Anhydrous Racemate of the Carcinostatic Agent Cyclophosphamide and the Bicyclic Degradation Product 1-(2-Chloroethyl)tetrahydro-1<i>H</i>,5<i>H</i>-1,3,2-diazaphospholo[2,1-<i>b</i>][1,3,2]oxazaphosphorine 9-Oxide
Jones, P. G.; Thönnessen, H.; Fischer, A.; Neda, I.; Schmutzler, R.; Engel, J.; Kutscher, B.; Niemeyer, U.; Acta Crystallographica Section C 52 (1996) 2359–2363; doi:10.1107/S0108270196004866

data_2005357
_publ_section_title
;The Anhydrous Racemate of the Carcinostatic Agent Cyclophosphamide and the
 Bicyclic Degradation Product
 1-(2-Chloroethyl)tetrahydro-1<i>H</i>,5<i>H</i>-1,3,2-diazaphospholo[2,1-<i>b</i>][1,3,2]oxazaphosphorine
 9-Oxide
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2359
_journal_page_last               2363
_journal_paper_doi               10.1107/S0108270196004866
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C7 H14 Cl N2 O2 P'
_chemical_formula_weight         224.62
_chemical_name_systematic
;
 1-(2-chloroethyl)tetrahydro-1H,5H-
 [1.3.2]diazaphospholo[2.1-b][1.3.2]oxazaphosphorine 9-oxide
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 118.95(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.580(2)
_cell_length_b                   10.021(2)
_cell_length_c                   10.779(2)
_cell_measurement_reflns_used    58
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      10
_cell_volume                     1000.0(4)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1991)'
_computing_data_reduction        DIF4
_computing_molecular_graphics    'XP (Siemens, 1994b)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_measurement_device       'Stoe STADI-4'
_diffrn_measurement_method       \w/\q-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  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0102
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2012
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.80
_exptl_crystal_size_min          0.75
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.302
_refine_ls_extinction_coef       0.0223(17)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.077
_refine_ls_goodness_of_fit_obs   1.081
_refine_ls_hydrogen_treatment    'H atoms refined as riding, C-H 0.99\%A'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_restrained_S_obs      1.081
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_obs          0.0278
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.6358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0753
_refine_ls_wR_factor_obs         0.0732
_reflns_number_observed          1681
_reflns_number_total             1764
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            fg1178.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (14
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (20 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.6358P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.6358P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1000.0(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2005357