#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:45:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178580 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/91/4069106.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4069106
loop_
_publ_author_name
'Ranocchiari, Marco'
'Mezzetti, Antonio'
_publ_section_title
;
 PNNP Macrocycles: A New Class of Ligands for Asymmetric Catalysis
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1286
_journal_paper_doi               10.1021/om900028w
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C16 H16 O2 P'
_chemical_formula_weight         271.26
_chemical_name_common            'intermediate (R,S)-4'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   12.023(2)
_cell_length_b                   14.893(3)
_cell_length_c                   15.451(3)
_cell_measurement_reflns_used    4435
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.43
_cell_measurement_theta_min      2.31
_cell_volume                     2766.6(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0869
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27093
_diffrn_reflns_theta_full        28.43
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.9725
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs vers. 2.03'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0593
_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/[σ²(Fo²)+(0.0485P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                2342
_reflns_number_total             3461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900028w_si_001.cif
_cod_data_source_block           x
_cod_depositor_comments
;
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 
;
_cod_original_sg_symbol_H-M      P(b)(c)(a)
_cod_database_code               4069106
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.63011(5) 0.09538(4) 0.54669(4) 0.02830(17) Uani 1 1 d .
O1 O 0.54427(14) 0.22171(11) 0.38938(12) 0.0458(5) Uani 1 1 d .
O2 O 0.63634(17) 0.35329(11) 0.39718(13) 0.0585(6) Uani 1 1 d .
C1 C 0.74220(17) 0.13202(15) 0.47283(13) 0.0264(5) Uani 1 1 d .
C2 C 0.73405(19) 0.21574(14) 0.43141(14) 0.0302(5) Uani 1 1 d .
C3 C 0.8225(2) 0.24696(18) 0.38218(16) 0.0418(6) Uani 1 1 d .
H3A H 0.8172 0.3039 0.3549 0.050 Uiso 1 1 calc R
C4 C 0.9175(2) 0.19697(18) 0.37227(17) 0.0441(7) Uani 1 1 d .
H4A H 0.9781 0.2201 0.3397 0.053 Uiso 1 1 calc R
C5 C 0.9250(2) 0.11365(18) 0.40943(16) 0.0395(6) Uani 1 1 d .
H5A H 0.9896 0.0780 0.4009 0.047 Uiso 1 1 calc R
C6 C 0.83812(18) 0.08159(16) 0.45936(15) 0.0334(5) Uani 1 1 d .
H6A H 0.8441 0.0238 0.4850 0.040 Uiso 1 1 calc R
C7 C 0.6271(2) 0.26790(15) 0.43588(16) 0.0383(6) Uani 1 1 d .
H7A H 0.6037 0.2746 0.4976 0.046 Uiso 1 1 calc R
C8 C 0.4655(2) 0.28797(18) 0.36567(18) 0.0506(7) Uani 1 1 d .
H8A H 0.4086 0.2958 0.4114 0.061 Uiso 1 1 calc R
H8B H 0.4281 0.2721 0.3107 0.061 Uiso 1 1 calc R
C9 C 0.5346(3) 0.3709(2) 0.3556(2) 0.0715(10) Uani 1 1 d .
H9A H 0.5469 0.3843 0.2936 0.086 Uiso 1 1 calc R
H9B H 0.4971 0.4230 0.3827 0.086 Uiso 1 1 calc R
C10 C 0.70472(17) 0.01698(15) 0.61676(14) 0.0289(5) Uani 1 1 d .
C11 C 0.7183(2) -0.07446(17) 0.60167(17) 0.0407(6) Uani 1 1 d .
H11A H 0.6878 -0.1007 0.5509 0.049 Uiso 1 1 calc R
C12 C 0.7762(2) -0.12779(19) 0.66025(19) 0.0484(7) Uani 1 1 d .
H12A H 0.7853 -0.1901 0.6492 0.058 Uiso 1 1 calc R
C13 C 0.8204(2) -0.0903(2) 0.73435(18) 0.0526(8) Uani 1 1 d .
H13A H 0.8603 -0.1265 0.7743 0.063 Uiso 1 1 calc R
C14 C 0.8061(3) -0.0009(2) 0.74972(18) 0.0608(9) Uani 1 1 d .
H14A H 0.8368 0.0253 0.8005 0.073 Uiso 1 1 calc R
C15 C 0.7477(2) 0.05194(19) 0.69239(16) 0.0450(7) Uani 1 1 d .
H15A H 0.7367 0.1137 0.7052 0.054 Uiso 1 1 calc R
C16 C 0.54943(17) 0.02034(15) 0.47559(13) 0.0288(5) Uani 1 1 d .
H16A H 0.5220 0.0546 0.4250 0.043 Uiso 1 1 calc R
H16B H 0.5981 -0.0284 0.4541 0.043 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C10 P1 C16 102.95(10) .
C10 P1 C1 101.33(10) .
C16 P1 C1 101.23(10) .
C7 O1 C8 105.35(18) .
C9 O2 C7 107.1(2) .
C6 C1 C2 117.9(2) .
C6 C1 P1 122.49(17) .
C2 C1 P1 119.50(17) .
C3 C2 C1 119.6(2) .
C3 C2 C7 120.5(2) .
C1 C2 C7 119.8(2) .
C4 C3 C2 121.2(2) .
C5 C4 C3 119.9(2) .
C4 C5 C6 119.8(2) .
C5 C6 C1 121.5(2) .
O1 C7 O2 106.25(19) .
O1 C7 C2 109.22(19) .
O2 C7 C2 112.3(2) .
O1 C8 C9 103.4(2) .
O2 C9 C8 106.4(2) .
C15 C10 C11 117.9(2) .
C15 C10 P1 116.39(19) .
C11 C10 P1 125.71(18) .
C12 C11 C10 120.6(3) .
C13 C12 C11 120.1(3) .
C14 C13 C12 119.4(3) .
C13 C14 C15 120.6(3) .
C14 C15 C10 121.4(3) .
C16 C16 P1 110.77(19) 5_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C10 1.828(2) .
P1 C16 1.843(2) .
P1 C1 1.848(2) .
O1 C7 1.408(3) .
O1 C8 1.416(3) .
O2 C9 1.406(3) .
O2 C7 1.410(3) .
C1 C6 1.392(3) .
C1 C2 1.405(3) .
C2 C3 1.388(3) .
C2 C7 1.503(3) .
C3 C4 1.372(3) .
C4 C5 1.370(3) .
C5 C6 1.383(3) .
C8 C9 1.496(4) .
C10 C15 1.380(3) .
C10 C11 1.391(3) .
C11 C12 1.391(3) .
C12 C13 1.380(4) .
C13 C14 1.364(4) .
C14 C15 1.377(4) .
C16 C16 1.533(4) 5_656
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C10 P1 C1 C6 21.7(2) .
C16 P1 C1 C6 -84.1(2) .
C10 P1 C1 C2 -155.14(17) .
C16 P1 C1 C2 99.03(18) .
C6 C1 C2 C3 -2.8(3) .
P1 C1 C2 C3 174.19(17) .
C6 C1 C2 C7 173.2(2) .
P1 C1 C2 C7 -9.8(3) .
C1 C2 C3 C4 0.8(3) .
C7 C2 C3 C4 -175.1(2) .
C2 C3 C4 C5 1.8(4) .
C3 C4 C5 C6 -2.3(4) .
C4 C5 C6 C1 0.2(4) .
C2 C1 C6 C5 2.3(3) .
P1 C1 C6 C5 -174.58(18) .
C8 O1 C7 O2 -34.8(3) .
C8 O1 C7 C2 -156.2(2) .
C9 O2 C7 O1 23.8(3) .
C9 O2 C7 C2 143.1(2) .
C3 C2 C7 O1 108.6(2) .
C1 C2 C7 O1 -67.4(3) .
C3 C2 C7 O2 -9.0(3) .
C1 C2 C7 O2 175.0(2) .
C7 O1 C8 C9 31.0(3) .
C7 O2 C9 C8 -4.1(3) .
O1 C8 C9 O2 -16.6(3) .
C16 P1 C10 C15 -162.18(18) .
C1 P1 C10 C15 93.35(19) .
C16 P1 C10 C11 15.5(2) .
C1 P1 C10 C11 -88.9(2) .
C15 C10 C11 C12 -1.8(4) .
P1 C10 C11 C12 -179.44(18) .
C10 C11 C12 C13 0.3(4) .
C11 C12 C13 C14 0.4(4) .
C12 C13 C14 C15 0.4(4) .
C13 C14 C15 C10 -1.9(4) .
C11 C10 C15 C14 2.6(4) .
P1 C10 C15 C14 -179.5(2) .
C10 P1 C16 C16 74.5(2) 5_656
C1 P1 C16 C16 179.1(2) 5_656
