#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/29/1502969.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_1502969
loop_
_publ_author_name
'Ackermann, Lutz'
'Kapdi, Anant R.'
'Schulzke, Carola'
_publ_section_title
;
 Air-stable secondary phosphine oxide or chloride (Pre)ligands for
 cross-couplings of unactivated alkyl chlorides.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2298
_journal_page_last               2301
_journal_paper_doi               10.1021/ol100658y
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C18 H22 Cl O2 P'
_chemical_formula_weight         336.78
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.16(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1373(18)
_cell_length_b                   14.932(3)
_cell_length_c                   12.950(3)
_cell_measurement_reflns_used    11288
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      53.9
_cell_measurement_theta_min      3.2
_cell_volume                     1727.2(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  IPDSII
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11020
_diffrn_reflns_theta_full        26.95
_diffrn_reflns_theta_max         26.95
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.8585
_exptl_absorpt_correction_T_min  0.7853
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'face indexed'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0410P)²+0.6638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                3467
_reflns_number_total             3697
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100658y_si_002.cif
_cod_data_source_block           akb83
_cod_original_cell_volume        1727.2(6)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1502969
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 C 0.36317(13) 0.28265(8) 0.59741(10) 0.0222(2) Uani 1 1 d
C2 C 0.34815(15) 0.34412(10) 0.68942(11) 0.0297(3) Uani 1 1 d
C3 C 0.45908(15) 0.32908(10) 0.52891(12) 0.0305(3) Uani 1 1 d
C4 C 0.43461(15) 0.19435(9) 0.63980(12) 0.0280(3) Uani 1 1 d
C5 C 0.07195(12) 0.19692(8) 0.58926(9) 0.0184(2) Uani 1 1 d
C6 C 0.08585(13) 0.10363(8) 0.58631(10) 0.0221(2) Uani 1 1 d
C7 C 0.00459(14) 0.04843(8) 0.63977(10) 0.0241(3) Uani 1 1 d
C8 C -0.09173(14) 0.08553(9) 0.69769(10) 0.0241(3) Uani 1 1 d
C9 C -0.10593(13) 0.17780(8) 0.70213(10) 0.0215(2) Uani 1 1 d
C10 C -0.02605(12) 0.23445(8) 0.64800(9) 0.0183(2) Uani 1 1 d
C11 C -0.04820(12) 0.33339(8) 0.65456(9) 0.0188(2) Uani 1 1 d
C12 C 0.00486(13) 0.37949(8) 0.74950(9) 0.0200(2) Uani 1 1 d
C13 C -0.01701(14) 0.47138(8) 0.75678(10) 0.0239(3) Uani 1 1 d
C14 C -0.09133(14) 0.51731(8) 0.66808(11) 0.0253(3) Uani 1 1 d
C15 C -0.14609(13) 0.47391(8) 0.57338(10) 0.0233(2) Uani 1 1 d
C16 C -0.12622(12) 0.38172(8) 0.56744(9) 0.0199(2) Uani 1 1 d
C17 C 0.15841(17) 0.37431(10) 0.92334(11) 0.0295(3) Uani 1 1 d
C18 C -0.25728(15) 0.37855(9) 0.38750(10) 0.0257(3) Uani 1 1 d
O1 O 0.07972(10) 0.32847(6) 0.83145(7) 0.02308(19) Uani 1 1 d
O2 O -0.17951(9) 0.33213(6) 0.47925(7) 0.02306(19) Uani 1 1 d
P1 P 0.16929(3) 0.27328(2) 0.51425(2) 0.02034(9) Uani 1 1 d
Cl1 Cl 0.21283(3) 0.18447(2) 0.39770(2) 0.02814(10) Uani 1 1 d
H2A H 0.2912(19) 0.3161(11) 0.7370(14) 0.033(4) Uiso 1 1 d
H2B H 0.295(2) 0.4026(13) 0.6647(14) 0.040(5) Uiso 1 1 d
H2C H 0.448(2) 0.3612(12) 0.7314(15) 0.043(5) Uiso 1 1 d
H3A H 0.415(2) 0.3862(13) 0.5014(14) 0.040(5) Uiso 1 1 d
H3B H 0.557(2) 0.3444(12) 0.5735(14) 0.038(5) Uiso 1 1 d
H3C H 0.475(2) 0.2881(12) 0.4685(15) 0.040(5) Uiso 1 1 d
H4A H 0.535(2) 0.2071(12) 0.6793(15) 0.039(5) Uiso 1 1 d
H4B H 0.4370(19) 0.1544(12) 0.5798(14) 0.035(4) Uiso 1 1 d
H4C H 0.3797(19) 0.1640(11) 0.6883(13) 0.032(4) Uiso 1 1 d
H6 H 0.1503(17) 0.0781(10) 0.5456(12) 0.023(4) Uiso 1 1 d
H7 H 0.0146(18) -0.0157(12) 0.6373(13) 0.030(4) Uiso 1 1 d
H8 H -0.1480(19) 0.0475(11) 0.7351(13) 0.032(4) Uiso 1 1 d
H9 H -0.1696(18) 0.2034(11) 0.7434(13) 0.029(4) Uiso 1 1 d
H13 H 0.0181(18) 0.5040(12) 0.8209(14) 0.032(4) Uiso 1 1 d
H14 H -0.1022(18) 0.5812(12) 0.6721(13) 0.033(4) Uiso 1 1 d
H15 H -0.1947(18) 0.5089(11) 0.5141(13) 0.029(4) Uiso 1 1 d
H17A H 0.2337(19) 0.4170(12) 0.9054(13) 0.035(4) Uiso 1 1 d
H17B H 0.211(2) 0.3260(12) 0.9707(15) 0.038(5) Uiso 1 1 d
H17C H 0.087(2) 0.4063(12) 0.9591(14) 0.037(4) Uiso 1 1 d
H18A H -0.1905(19) 0.4226(12) 0.3628(13) 0.035(4) Uiso 1 1 d
H18B H -0.3449(19) 0.4114(11) 0.4034(13) 0.030(4) Uiso 1 1 d
H18C H -0.2929(18) 0.3308(11) 0.3354(14) 0.031(4) 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 0.0000 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'
Cl Cl 0.1484 0.1585 '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
C4 C1 C2 109.90(11)
C4 C1 C3 110.22(10)
C2 C1 C3 109.50(11)
C4 C1 P1 115.10(9)
C2 C1 P1 105.23(8)
C3 C1 P1 106.67(9)
C6 C5 C10 118.85(11)
C6 C5 P1 122.98(9)
C10 C5 P1 118.09(9)
C7 C6 C5 121.08(11)
C8 C7 C6 119.98(12)
C9 C8 C7 119.69(11)
C8 C9 C10 121.15(11)
C9 C10 C5 119.25(11)
C9 C10 C11 118.55(10)
C5 C10 C11 122.20(10)
C16 C11 C12 118.43(11)
C16 C11 C10 120.99(10)
C12 C11 C10 120.55(10)
O1 C12 C13 123.51(11)
O1 C12 C11 115.51(10)
C13 C12 C11 120.97(11)
C14 C13 C12 118.91(12)
C15 C14 C13 121.67(12)
C14 C15 C16 119.00(12)
O2 C16 C15 123.77(11)
O2 C16 C11 115.25(11)
C15 C16 C11 120.98(11)
C12 O1 C17 117.47(10)
C16 O2 C18 117.44(10)
C5 P1 C1 104.24(6)
C5 P1 Cl1 99.96(4)
C1 P1 Cl1 99.21(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C4 1.5215(18)
C1 C2 1.5330(18)
C1 C3 1.5372(18)
C1 P1 1.8745(14)
C5 C6 1.4000(17)
C5 C10 1.4077(16)
C5 P1 1.8436(12)
C6 C7 1.3880(18)
C7 C8 1.3865(18)
C8 C9 1.3862(18)
C9 C10 1.3982(17)
C10 C11 1.4959(16)
C11 C16 1.4011(17)
C11 C12 1.4034(17)
C12 O1 1.3670(15)
C12 C13 1.3926(17)
C13 C14 1.3864(19)
C14 C15 1.3841(19)
C15 C16 1.3928(17)
C16 O2 1.3620(15)
C17 O1 1.4286(16)
C18 O2 1.4288(15)
P1 Cl1 2.1090(6)
