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_4030149
_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 Br Cl N O2 P'
_chemical_formula_sum            'C30 H24 Br Cl N O2 P'
_chemical_formula_weight         576.83
_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                   11.5133(6)
_cell_length_b                   14.2627(16)
_cell_length_c                   16.305(3)
_cell_measurement_reflns_used    107
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.49
_cell_measurement_theta_min      3.82
_cell_volume                     2677.5(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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.1224
_diffrn_reflns_av_sigmaI/netI    0.1411
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17836
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         5.00
_exptl_absorpt_coefficient_mu    1.723
_exptl_absorpt_correction_T_max  0.9343
_exptl_absorpt_correction_T_min  0.8331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.476
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.019(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         6003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1727
_refine_ls_R_factor_gt           0.0677
_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^)+(0.0329P)^2^+1.1989P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1425
_reflns_number_gt                2855
_reflns_number_total             6003
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502094g_si_005.cif
_cod_data_source_block           ff5
_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.
;
_cod_original_cell_volume        2677.5(5)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               4030149