Stacked naphthyls and weak hydrogen-bond interactions govern the conformational behavior of P-resolved cyclic phosphonamides: a combined experimental and computational study.
Capozzi, Maria Annunziata M.; Capitelli, Francesco; Bottoni, Andrea; Calvaresi, Matteo; Cardellicchio, Cosimo; The Journal of organic chemistry 79 (2014) 11101–11109; doi:10.1021/jo502094g

data_4030147
_publ_contact_author             'Dr. Francesco Capitelli'
_publ_section_title
;
 Stacked naphthyls and weak hydrogen-bond interactions govern the
 conformational behavior of P-resolved cyclic phosphonamides: a combined
 experimental and computational study.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11101
_journal_page_last               11109
_journal_paper_doi               10.1021/jo502094g
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C30 H24 Cl F N O2 P'
_chemical_formula_weight         515.92
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.6360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4670(10)
_cell_length_b                   14.5630(10)
_cell_length_c                   20.469(4)
_cell_measurement_reflns_used    251
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.46
_cell_measurement_theta_min      5.03
_cell_volume                     2522.9(6)
_computing_cell_refinement       'EVALCCD (Duisenberg et al., 2003)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'DIAMOND 2.1e (1998-2001 Crystal Impact GbR)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al. 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_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  0.0835
_diffrn_reflns_av_sigmaI/netI    0.1498
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23729
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         5.02
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.9633
_exptl_absorpt_correction_T_min  0.9106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         10682
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1609
_refine_ls_R_factor_gt           0.0617
_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^)+(0.0295P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1151
_reflns_number_gt                5571
_reflns_number_total             10682
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502094g_si_003.cif
_cod_data_source_block           cb80
_cod_depositor_comments
'Adding full bibliography for 4030147--4030150.cif.'
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4030147