#------------------------------------------------------------------------------
#$Date: 2016-02-05 01:55:28 +0200 (Fri, 05 Feb 2016) $
#$Revision: 176069 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/62/7036297.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_7036297
loop_
_publ_author_name
'Del Águila-Sánchez, Miguel A'
'Navarro, Yolanda'
'García López, Jesús'
'Guedes, Guilherme P.'
'López Ortiz, Fernando'
_publ_section_title
;
 Synthesis of P-stereogenic diarylphosphinic amides by directed
 lithiation: transformation into tertiary phosphine oxides via
 methanolysis, aryne chemistry and complexation behaviour toward zinc(ii).
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2008
_journal_page_last               2022
_journal_paper_doi               10.1039/c5dt02860d
_journal_volume                  45
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18  H23  I N O P'
_chemical_formula_sum            'C18 H23 I N O P'
_chemical_formula_weight         427.24
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_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      2.4.3
_audit_creation_date             2015-08-20T15:32:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-08-21 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1337(7)
_cell_length_b                   10.2928(7)
_cell_length_c                   18.6620(13)
_cell_measurement_reflns_used    5287
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.06
_cell_measurement_theta_min      2.26
_cell_measurement_wavelength     0.71073
_cell_volume                     1946.5(2)
_computing_cell_refinement       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_collection       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_reduction        'Bruker Saint (Bruker AXS, 2007)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 2012) and Mercury (Macrae, 2008).'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker AXS Smart Apex'
_diffrn_measurement_method       'φ-ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_laue_measured_fraction_full 0.99
_diffrn_reflns_laue_measured_fraction_max 0.99
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9653
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        24.475
_diffrn_reflns_theta_max         24.475
_diffrn_reflns_theta_min         2.821
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.729
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS, Bruker Analytical X-ray Systems,Inc., Madison WI, 1997.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate:hexane'
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.325
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1214 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0463P)²+0.1930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0816
_reflns_Friedel_coverage         0.728
_reflns_friedel_fraction_full    0.979
_reflns_friedel_fraction_max     0.979
_reflns_number_gt                3062
_reflns_number_total             3222
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt02860d1.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7036296--7036299.cif.'
_cod_database_code               7036297
_publcif_datablock.id            {5a205740-5491-4371-b787-cae9e39dd455}
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'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
I1 I 0.88280(4) 0.98692(4) 0.92941(2) 0.06469(17) Uani 1 1 d . .
P1 P 1.18489(14) 1.15600(13) 0.97131(7) 0.0424(3) Uani 1 1 d . .
O1 O 1.3218(4) 1.1923(4) 0.9874(2) 0.0553(10) Uani 1 1 d . .
C16 C 1.1306(9) 1.1102(11) 1.2371(4) 0.100(3) Uani 1 1 d . .
H16A H 1.2251 1.1162 1.2357 0.149 Uiso 1 1 calc R U
H16B H 1.0947 1.1895 1.2559 0.149 Uiso 1 1 calc R U
H16C H 1.1053 1.0389 1.2673 0.149 Uiso 1 1 calc R U
N1 N 1.0836(5) 1.1848(5) 1.0372(2) 0.0455(11) Uani 1 1 d . .
C17 C 1.1351(9) 0.9611(8) 1.1338(4) 0.092(2) Uani 1 1 d . .
H17A H 1.2296 0.9679 1.1324 0.138 Uiso 1 1 calc R U
H17B H 1.1102 0.8918 1.1655 0.138 Uiso 1 1 calc R U
H17C H 1.1023 0.9435 1.0866 0.138 Uiso 1 1 calc R U
C7 C 1.1192(6) 1.2381(5) 0.8939(3) 0.0455(12) Uani 1 1 d . .
C13 C 1.1245(6) 1.2015(6) 1.1123(3) 0.0547(14) Uani 1 1 d . .
H13 H 1.2212 1.202 1.1133 0.066 Uiso 1 1 calc R U
C1 C 1.1846(5) 0.9836(5) 0.9474(3) 0.0477(12) Uani 1 1 d . .
C5 C 1.3177(8) 0.7924(7) 0.9299(5) 0.081(2) Uani 1 1 d . .
H5 H 1.4003 0.753 0.9288 0.097 Uiso 1 1 calc R U
C10 C 1.0444(7) 1.3778(7) 0.7741(4) 0.0690(18) Uani 1 1 d . .
H10 H 1.0189 1.4248 0.7339 0.083 Uiso 1 1 calc R U
C6 C 1.3071(7) 0.9226(6) 0.9454(3) 0.0631(16) Uani 1 1 d . .
H6 H 1.383 0.9706 0.9546 0.076 Uiso 1 1 calc R U
C15 C 1.0773(7) 1.0875(7) 1.1607(3) 0.0654(17) Uani 1 1 d . .
C2 C 1.0738(6) 0.9085(5) 0.9319(3) 0.0524(13) Uani 1 1 d . .
C9 C 1.1057(9) 1.2596(8) 0.7666(3) 0.076(2) Uani 1 1 d . .
H9 H 1.1217 1.2261 0.7211 0.092 Uiso 1 1 calc R U
C4 C 1.2068(10) 0.7206(7) 0.9160(5) 0.088(2) Uani 1 1 d . .
H4 H 1.2144 0.6324 0.906 0.106 Uiso 1 1 calc R U
C3 C 1.0841(9) 0.7778(6) 0.9168(4) 0.076(2) Uani 1 1 d . .
H3 H 1.009 0.729 0.9071 0.091 Uiso 1 1 calc R U
C8 C 1.1435(7) 1.1908(6) 0.8263(3) 0.0616(16) Uani 1 1 d . .
H8 H 1.186 1.1113 0.8209 0.074 Uiso 1 1 calc R U
C11 C 1.0213(7) 1.4253(6) 0.8407(4) 0.0659(17) Uani 1 1 d . .
H11 H 0.9801 1.5056 0.8457 0.079 Uiso 1 1 calc R U
C12 C 1.0572(6) 1.3579(6) 0.9006(3) 0.0555(14) Uani 1 1 d . .
H12 H 1.0402 1.3921 0.9458 0.067 Uiso 1 1 calc R U
C14 C 1.0777(7) 1.3349(7) 1.1373(4) 0.0736(19) Uani 1 1 d . .
H14A H 1.1034 1.3479 1.1863 0.11 Uiso 1 1 calc R U
H14B H 1.1169 1.401 1.1079 0.11 Uiso 1 1 calc R U
H14C H 0.9834 1.3397 1.1336 0.11 Uiso 1 1 calc R U
C18 C 0.9303(7) 1.0781(10) 1.1632(4) 0.089(3) Uani 1 1 d . .
H18A H 0.8943 1.1586 1.1803 0.134 Uiso 1 1 calc R U
H18B H 0.8971 1.0607 1.116 0.134 Uiso 1 1 calc R U
H18C H 0.9049 1.0089 1.1948 0.134 Uiso 1 1 calc R U
H1 H 1.010(5) 1.202(5) 1.034(3) 0.024(13) Uiso 1 1 d . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
I I -0.4742 1.8119 '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
O1 P1 N1 113.3(2)
O1 P1 C7 113.2(3)
N1 P1 C7 106.7(3)
O1 P1 C1 107.4(3)
N1 P1 C1 111.0(3)
C7 P1 C1 105.0(2)
C13 N1 P1 124.2(4)
C8 C7 C12 118.6(5)
C8 C7 P1 120.3(4)
C12 C7 P1 120.7(4)
N1 C13 C14 108.0(5)
N1 C13 C15 112.2(5)
C14 C13 C15 113.9(5)
C6 C1 C2 117.6(5)
C6 C1 P1 116.3(5)
C2 C1 P1 126.1(4)
C4 C5 C6 120.1(7)
C11 C10 C9 119.5(6)
C5 C6 C1 121.0(7)
C18 C15 C17 109.9(7)
C18 C15 C16 109.3(6)
C17 C15 C16 107.5(6)
C18 C15 C13 111.9(6)
C17 C15 C13 109.7(5)
C16 C15 C13 108.4(6)
C3 C2 C1 121.5(6)
C3 C2 I1 116.1(5)
C1 C2 I1 122.3(4)
C8 C9 C10 119.9(6)
C5 C4 C3 120.6(6)
C4 C3 C2 119.2(7)
C9 C8 C7 120.8(6)
C10 C11 C12 121.4(6)
C11 C12 C7 119.8(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C2 2.098(6)
P1 O1 1.467(4)
P1 N1 1.629(5)
P1 C7 1.801(6)
P1 C1 1.830(6)
C16 C15 1.542(9)
N1 C13 1.471(7)
C17 C15 1.512(11)
C7 C8 1.374(8)
C7 C12 1.390(8)
C13 C14 1.526(10)
C13 C15 1.557(9)
C1 C6 1.392(8)
C1 C2 1.393(8)
C5 C4 1.370(12)
C5 C6 1.375(10)
C10 C11 1.357(10)
C10 C9 1.374(11)
C15 C18 1.494(10)
C2 C3 1.378(8)
C9 C8 1.374(10)
C4 C3 1.375(12)
C11 C12 1.365(9)
