On the Existence of the Chair Conformation in Six-Membered Ring Phosphates Bearing an Aryl Group Axially Oriented at the C4 Position: Cyclic Nucleotides As Model Compounds for Cyclic Phosph(on)ate and Phosphoramide Prodrugs
Leticia Quintero; Mario Sánchez-Vazquez; Silvano Cruz-Gregorio; Fernando Sartillo-Piscil; Journal of Organic Chemistry 75 (2010) 5852–5859; doi:10.1021/jo100863n

data_4025611
_publ_contact_author_address
;
Centro de Qu\'imica
ICUAP
Benem\'erita Universidad Aut\'onoma de Pueba
Puebla, Puebla
M\'exico
;
_publ_contact_author_email       angel.mendoza.m@gmail.com
_publ_contact_author_fax         '+52 222 229 55 00 ext 7397'
_publ_contact_author_name        'Mendoza, Angel'
_publ_contact_author_phone       '+52 222 229 55 00 ext 7297'
_publ_section_title
;
 On the Existence of the Chair Conformation in Six-Membered Ring
 Phosphates Bearing an Aryl Group Axially Oriented at the C4 Position:
 Cyclic Nucleotides As Model Compounds for Cyclic Phosph(on)ate and
 Phosphoramide Prodrugs
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5852
_journal_page_last               5859
_journal_paper_doi               10.1021/jo100863n
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C27 H32 Cl1 N2 O12 P1'
_chemical_formula_sum            'C27 H32 Cl N2 O12 P'
_chemical_formula_weight         642.97
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2009-06-02T19:20:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.00
_cell_angle_beta                 97.800(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.648(3)
_cell_length_b                   10.193(4)
_cell_length_c                   13.876(3)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.998
_cell_measurement_theta_min      9.733
_cell_measurement_wavelength     0.71073
_cell_volume                     1492.1(8)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'ORTEP 3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.1235
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4528
_diffrn_reflns_theta_full        29
_diffrn_reflns_theta_max         29
_diffrn_reflns_theta_min         1.48
_diffrn_standards_decay_%        2.35
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.36
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(15)
_refine_ls_extinction_coef       0.0093(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4178
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.873
_refine_ls_R_factor_all          0.1913
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1511
_reflns_number_gt                1435
_reflns_number_total             4178
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo100863n_si_002.cif
_cod_data_source_block           pphcl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025611