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_4030148
_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_moiety         'C30 H24 Cl2 N O2 P'
_chemical_formula_sum            'C30 H24 Cl2 N O2 P'
_chemical_formula_weight         532.37
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.540(2)
_cell_length_b                   14.080(7)
_cell_length_c                   16.285(3)
_cell_measurement_reflns_used    176
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.10
_cell_measurement_theta_min      3.44
_cell_volume                     2646.0(15)
_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 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.1037
_diffrn_reflns_av_sigmaI/netI    0.0898
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23741
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         5.01
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.18(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         6017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0642
_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^)+(0.0784P)^2^+1.0037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1778
_reflns_number_gt                3774
_reflns_number_total             6017
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502094g_si_004.cif
_cod_data_source_block           ff6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2930 2014-11-03 09:23:46Z andrius 

 Adding full bibliography for 4030147--4030150.cif.
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_cod_original_sg_symbol_H-M      P212121
_cod_database_code               4030148