#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202226.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_2202226
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o493
_journal_page_last  o494
_publ_section_title
;
3-Bromo-4-(dicyclohexylphosphinoyl)-2,6-dimethoxypyridine
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
loop_
_publ_author_name
  'Wu, Jing'
  'Guo, Rongwei'
  'Zhou, Zhongyuan'
  'Chen, Hua'
  'Yeung, Chihung'
_chemical_formula_moiety  'C19 H29 Br N O3 P'
_chemical_formula_sum  'C19 H29 Br N O3 P'
_chemical_formula_iupac  'C19 H29 Br N O3 P'
_chemical_formula_weight  430.31
_symmetry_cell_setting  Monoclinic
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'
_cell_length_a  9.2025(12)
_cell_length_b  18.759(2)
_cell_length_c  23.761(3)
_cell_angle_alpha  90.00
_cell_angle_beta  92.009(3)
_cell_angle_gamma  90.00
_cell_volume  4099.3(9)
_cell_formula_units_Z  8
_cell_measurement_temperature  294(2)
_exptl_crystal_density_diffrn  1.394
_diffrn_ambient_temperature  294(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  Br1 0.37202(5) 0.30717(3) 0.55442(2) 0.06490(18) Uani d . 1 . . Br
  P1 0.22148(13) 0.35103(7) 0.41928(5) 0.0532(3) Uani d . 1 . . P
  O1 0.1201(3) 0.36109(17) 0.37024(11) 0.0722(10) Uani d . 1 . . O
  O2 0.1533(3) 0.22404(17) 0.61400(13) 0.0655(9) Uani d . 1 . . O
  O3 -0.2073(4) 0.20364(19) 0.47620(12) 0.0770(10) Uani d . 1 . . O
  N1 -0.0290(4) 0.21495(19) 0.54593(14) 0.0493(10) Uani d . 1 . . N
  C1 0.3831(5) 0.2989(2) 0.40401(18) 0.0543(12) Uani d . 1 . . C
  H1A 0.4315 0.2889 0.4405 0.065 Uiso calc R 1 . . H
  C2 0.4918(6) 0.3365(3) 0.3703(2) 0.0870(18) Uani d . 1 . . C
  H2A 0.5296 0.3769 0.3918 0.104 Uiso calc R 1 . . H
  H2B 0.4439 0.3550 0.3364 0.104 Uiso calc R 1 . . H
  C3 0.6155(6) 0.2907(3) 0.3543(3) 0.0944(19) Uani d . 1 . . C
  H3A 0.6778 0.2825 0.3875 0.113 Uiso calc R 1 . . H
  H3B 0.6722 0.3163 0.3272 0.113 Uiso calc R 1 . . H
  C4 0.5727(7) 0.2203(3) 0.3297(3) 0.107(2) Uani d . 1 . . C
  H4A 0.5306 0.2275 0.2921 0.128 Uiso calc R 1 . . H
  H4B 0.6587 0.1909 0.3266 0.128 Uiso calc R 1 . . H
  C5 0.4682(7) 0.1835(3) 0.3639(3) 0.118(2) Uani d . 1 . . C
  H5A 0.5180 0.1668 0.3981 0.142 Uiso calc R 1 . . H
  H5B 0.4327 0.1419 0.3434 0.142 Uiso calc R 1 . . H
  C6 0.3402(6) 0.2279(3) 0.3798(2) 0.0917(19) Uani d . 1 . . C
  H6A 0.2774 0.2353 0.3467 0.110 Uiso calc R 1 . . H
  H6B 0.2850 0.2021 0.4073 0.110 Uiso calc R 1 . . H
  C7 0.2827(5) 0.4360(2) 0.44960(16) 0.0450(11) Uani d . 1 . . C
  H7A 0.3785 0.4286 0.4680 0.054 Uiso calc R 1 . . H
  C8 0.1816(5) 0.4673(3) 0.49314(19) 0.0656(14) Uani d . 1 . . C
  H8A 0.0846 0.4720 0.4763 0.079 Uiso calc R 1 . . H
  H8B 0.1765 0.4348 0.5247 0.079 Uiso calc R 1 . . H
  C9 0.2329(5) 0.5393(3) 0.51426(19) 0.0683(14) Uani d . 1 . . C
  H9A 0.1632 0.5581 0.5401 0.082 Uiso calc R 1 . . H
  H9B 0.3252 0.5338 0.5348 0.082 Uiso calc R 1 . . H
  C10 0.2508(6) 0.5915(3) 0.4669(2) 0.0839(17) Uani d . 1 . . C
  H10A 0.2910 0.6357 0.4818 0.101 Uiso calc R 1 . . H
  H10B 0.1565 0.6018 0.4492 0.101 Uiso calc R 1 . . H
  C11 0.3509(6) 0.5613(3) 0.4233(2) 0.0799(17) Uani d . 1 . . C
  H11A 0.3556 0.5944 0.3920 0.096 Uiso calc R 1 . . H
  H11B 0.4482 0.5566 0.4400 0.096 Uiso calc R 1 . . H
  C12 0.3001(5) 0.4890(2) 0.40137(18) 0.0641(14) Uani d . 1 . . C
  H12A 0.3701 0.4706 0.3755 0.077 Uiso calc R 1 . . H
  H12B 0.2078 0.4945 0.3809 0.077 Uiso calc R 1 . . H
  C13 0.1291(5) 0.2984(2) 0.47399(16) 0.0440(11) Uani d . 1 . . C
  C14 0.1844(4) 0.2811(2) 0.52684(18) 0.0479(12) Uani d . 1 . . C
  C15 0.1003(5) 0.2396(2) 0.56209(18) 0.0498(12) Uani d . 1 . . C
  C16 -0.0792(5) 0.2307(3) 0.4938(2) 0.0539(12) Uani d . 1 . . C
  C17 -0.0032(5) 0.2738(2) 0.45722(19) 0.0572(13) Uani d . 1 . . C
  H17A -0.0430 0.2855 0.4219 0.069 Uiso calc R 1 . . H
  C18 0.0722(5) 0.1757(3) 0.64868(19) 0.0787(17) Uani d . 1 . . C
  H18A 0.1228 0.1696 0.6844 0.118 Uiso calc R 1 . . H
  H18B 0.0627 0.1304 0.6301 0.118 Uiso calc R 1 . . H
  H18C -0.0227 0.1951 0.6545 0.118 Uiso calc R 1 . . H
  C19 -0.2789(6) 0.1560(3) 0.5116(2) 0.101(2) Uani d . 1 . . C
  H19A -0.3690 0.1412 0.4936 0.151 Uiso calc R 1 . . H
  H19B -0.2981 0.1792 0.5466 0.151 Uiso calc R 1 . . H
  H19C -0.2185 0.1150 0.5187 0.151 Uiso calc R 1 . . H
  Br2 0.85647(5) 0.04305(3) 0.747128(18) 0.06861(19) Uani d . 1 . . Br
  P2 0.49520(12) 0.07662(7) 0.69441(4) 0.0456(3) Uani d . 1 . . P
  O4 0.3660(3) 0.08126(16) 0.65554(11) 0.0575(8) Uani d . 1 . . O
  O5 1.0107(3) -0.03275(18) 0.65904(12) 0.0719(10) Uani d . 1 . . O
  O6 0.6551(4) -0.04846(18) 0.51877(12) 0.0789(11) Uani d . 1 . . O
  N2 0.8342(4) -0.04124(19) 0.58850(15) 0.0533(10) Uani d . 1 . . N
  C20 0.4615(5) 0.0253(2) 0.75805(16) 0.0527(12) Uani d . 1 . . C
  H20A 0.5261 0.0436 0.7884 0.063 Uiso calc R 1 . . H
  C21 0.4891(6) -0.0536(2) 0.75249(19) 0.0708(15) Uani d . 1 . . C
  H21A 0.5902 -0.0611 0.7439 0.085 Uiso calc R 1 . . H
  H21B 0.4296 -0.0722 0.7213 0.085 Uiso calc R 1 . . H
  C22 0.4556(7) -0.0946(3) 0.8055(2) 0.0893(18) Uani d . 1 . . C
  H22A 0.5215 -0.0796 0.8359 0.107 Uiso calc R 1 . . H
  H22B 0.4708 -0.1451 0.7992 0.107 Uiso calc R 1 . . H
  C23 0.3000(7) -0.0823(3) 0.8222(2) 0.104(2) Uani d . 1 . . C
  H23A 0.2337 -0.1029 0.7939 0.125 Uiso calc R 1 . . H
  H23B 0.2837 -0.1057 0.8578 0.125 Uiso calc R 1 . . H
  C24 0.2700(7) -0.0042(4) 0.8275(2) 0.116(2) Uani d . 1 . . C
  H24A 0.3274 0.0146 0.8592 0.139 Uiso calc R 1 . . H
  H24B 0.1682 0.0025 0.8354 0.139 Uiso calc R 1 . . H
  C25 0.3048(6) 0.0376(3) 0.7749(2) 0.0874(18) Uani d . 1 . . C
  H25A 0.2899 0.0880 0.7817 0.105 Uiso calc R 1 . . H
  H25B 0.2390 0.0232 0.7442 0.105 Uiso calc R 1 . . H
  C26 0.5657(4) 0.1628(2) 0.71600(16) 0.0457(11) Uani d . 1 . . C
  H26A 0.6390 0.1547 0.7462 0.055 Uiso calc R 1 . . H
  C27 0.4483(5) 0.2098(2) 0.73966(19) 0.0647(14) Uani d . 1 . . C
  H27A 0.4069 0.1862 0.7717 0.078 Uiso calc R 1 . . H
  H27B 0.3712 0.2164 0.7112 0.078 Uiso calc R 1 . . H
  C28 0.5077(6) 0.2828(3) 0.7581(2) 0.0740(16) Uani d . 1 . . C
  H28A 0.4287 0.3121 0.7710 0.089 Uiso calc R 1 . . H
  H28B 0.5775 0.2767 0.7893 0.089 Uiso calc R 1 . . H
  C29 0.5806(6) 0.3203(3) 0.7099(2) 0.0833(17) Uani d . 1 . . C
  H29A 0.6225 0.3649 0.7231 0.100 Uiso calc R 1 . . H
  H29B 0.5088 0.3309 0.6802 0.100 Uiso calc R 1 . . H
  C30 0.6997(6) 0.2730(3) 0.6867(2) 0.0864(17) Uani d . 1 . . C
  H30A 0.7418 0.2964 0.6547 0.104 Uiso calc R 1 . . H
  H30B 0.7760 0.2664 0.7153 0.104 Uiso calc R 1 . . H
  C31 0.6401(5) 0.2011(2) 0.66855(19) 0.0635(14) Uani d . 1 . . C
  H31A 0.7191 0.1717 0.6557 0.076 Uiso calc R 1 . . H
  H31B 0.5710 0.2076 0.6372 0.076 Uiso calc R 1 . . H
  C32 0.6408(5) 0.0305(2) 0.65661(15) 0.0415(11) Uani d . 1 . . C
  C33 0.7819(5) 0.0158(2) 0.67508(16) 0.0469(11) Uani d . 1 . . C
  C34 0.8745(5) -0.0190(2) 0.63953(19) 0.0512(12) Uani d . 1 . . C
  C35 0.6992(6) -0.0269(2) 0.57106(18) 0.0546(13) Uani d . 1 . . C
  C36 0.5997(5) 0.0085(2) 0.60255(17) 0.0502(12) Uani d . 1 . . C
  H36A 0.5065 0.0176 0.5879 0.060 Uiso calc R 1 . . H
  C37 1.1078(5) -0.0689(3) 0.6223(2) 0.0925(19) Uani d . 1 . . C
  H37A 1.2005 -0.0754 0.6414 0.139 Uiso calc R 1 . . H
  H37B 1.1198 -0.0408 0.5890 0.139 Uiso calc R 1 . . H
  H37C 1.0678 -0.1145 0.6121 0.139 Uiso calc R 1 . . H
  C38 0.7538(6) -0.0878(3) 0.4870(2) 0.0947(19) Uani d . 1 . . C
  H38A 0.7090 -0.0999 0.4512 0.142 Uiso calc R 1 . . H
  H38B 0.7804 -0.1307 0.5069 0.142 Uiso calc R 1 . . H
  H38C 0.8392 -0.0597 0.4814 0.142 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  Br1 0.0548(3) 0.0821(4) 0.0573(3) -0.0078(3) -0.0040(2) 0.0054(3)
  P1 0.0562(8) 0.0582(9) 0.0455(7) -0.0041(7) 0.0065(6) 0.0029(7)
  O1 0.081(2) 0.083(3) 0.0513(18) -0.006(2) -0.0153(17) 0.0075(18)
  O2 0.054(2) 0.079(3) 0.063(2) -0.0047(18) -0.0001(17) 0.0187(19)
  O3 0.060(2) 0.104(3) 0.066(2) -0.031(2) -0.0047(18) 0.017(2)
  N1 0.043(2) 0.053(3) 0.053(2) 0.000(2) 0.0125(19) 0.006(2)
  C1 0.061(3) 0.053(3) 0.050(3) -0.004(3) 0.016(2) -0.005(3)
  C2 0.075(4) 0.066(4) 0.123(5) 0.002(3) 0.044(4) 0.002(4)
  C3 0.075(4) 0.075(5) 0.136(5) 0.005(4) 0.049(4) 0.013(4)
  C4 0.101(5) 0.091(5) 0.130(5) 0.032(4) 0.035(4) -0.017(5)
  C5 0.144(6) 0.071(4) 0.146(6) -0.011(4) 0.091(5) -0.023(4)
  C6 0.099(5) 0.071(4) 0.109(4) -0.024(4) 0.048(4) -0.034(4)
  C7 0.049(3) 0.041(3) 0.045(2) 0.003(2) 0.008(2) 0.005(2)
  C8 0.073(4) 0.060(4) 0.065(3) 0.005(3) 0.016(3) 0.001(3)
  C9 0.073(4) 0.061(4) 0.071(3) 0.002(3) 0.005(3) -0.013(3)
  C10 0.106(5) 0.050(4) 0.096(4) 0.010(3) 0.002(4) -0.006(3)
  C11 0.116(5) 0.046(4) 0.079(4) -0.008(3) 0.013(3) 0.016(3)
  C12 0.088(4) 0.055(3) 0.050(3) -0.002(3) 0.006(3) 0.008(3)
  C13 0.048(3) 0.042(3) 0.042(2) 0.005(2) 0.009(2) 0.006(2)
  C14 0.041(3) 0.048(3) 0.055(3) -0.004(2) 0.006(2) -0.002(2)
  C15 0.050(3) 0.053(3) 0.047(3) 0.010(3) 0.008(2) 0.004(3)
  C16 0.049(3) 0.057(3) 0.056(3) -0.005(3) 0.008(3) 0.004(3)
  C17 0.053(3) 0.062(3) 0.056(3) -0.002(3) 0.003(3) -0.001(3)
  C18 0.065(4) 0.110(5) 0.062(3) 0.003(3) 0.014(3) 0.032(3)
  C19 0.075(4) 0.154(6) 0.072(4) -0.051(4) 0.003(3) 0.025(4)
  Br2 0.0607(3) 0.0930(4) 0.0515(3) 0.0121(3) -0.0075(2) -0.0178(3)
  P2 0.0424(7) 0.0519(8) 0.0427(6) 0.0027(6) 0.0061(5) -0.0041(6)
  O4 0.0463(19) 0.071(2) 0.0546(17) 0.0099(16) -0.0003(15) -0.0143(17)
  O5 0.051(2) 0.098(3) 0.067(2) 0.022(2) 0.0063(17) -0.018(2)
  O6 0.094(3) 0.092(3) 0.0496(19) 0.033(2) -0.0078(18) -0.0273(19)
  N2 0.063(3) 0.055(3) 0.043(2) 0.009(2) 0.014(2) -0.003(2)
  C20 0.058(3) 0.056(3) 0.045(3) -0.009(3) 0.014(2) -0.004(2)
  C21 0.084(4) 0.053(4) 0.076(3) 0.000(3) 0.023(3) 0.005(3)
  C22 0.111(5) 0.066(4) 0.092(4) -0.015(4) 0.019(4) 0.021(3)
  C23 0.116(6) 0.097(6) 0.101(5) -0.035(4) 0.042(4) 0.017(4)
  C24 0.113(6) 0.137(7) 0.102(5) -0.012(5) 0.067(4) 0.013(5)
  C25 0.086(4) 0.080(4) 0.100(4) 0.009(3) 0.059(4) 0.008(3)
  C26 0.043(3) 0.047(3) 0.047(2) 0.009(2) 0.001(2) 0.002(2)
  C27 0.072(4) 0.060(4) 0.064(3) 0.003(3) 0.022(3) -0.011(3)
  C28 0.091(4) 0.061(4) 0.070(3) 0.013(3) 0.003(3) -0.015(3)
  C29 0.091(4) 0.045(4) 0.114(5) 0.001(3) 0.004(4) -0.002(3)
  C30 0.070(4) 0.062(4) 0.129(5) -0.009(3) 0.029(4) 0.004(4)
  C31 0.065(3) 0.058(3) 0.070(3) 0.004(3) 0.023(3) 0.008(3)
  C32 0.051(3) 0.039(3) 0.035(2) -0.001(2) 0.008(2) -0.003(2)
  C33 0.048(3) 0.049(3) 0.044(2) 0.005(2) 0.007(2) -0.004(2)
  C34 0.048(3) 0.052(3) 0.054(3) 0.010(3) 0.008(2) 0.008(3)
  C35 0.071(4) 0.052(3) 0.041(3) 0.008(3) 0.006(3) -0.004(2)
  C36 0.049(3) 0.055(3) 0.047(3) 0.009(2) 0.002(2) -0.004(2)
  C37 0.057(4) 0.130(5) 0.091(4) 0.035(4) 0.014(3) -0.016(4)
  C38 0.125(5) 0.107(5) 0.052(3) 0.048(4) 0.008(3) -0.023(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  Br1 C14 . 1.890(4) ?
  P1 O1 . 1.479(3) ?
  P1 C1 . 1.826(4) ?
  P1 C7 . 1.830(4) ?
  P1 C13 . 1.861(4) ?
  O2 C15 . 1.342(5) ?
  O2 C18 . 1.450(5) ?
  O3 C16 . 1.337(5) ?
  O3 C19 . 1.407(5) ?
  N1 C15 . 1.322(5) ?
  N1 C16 . 1.340(5) ?
  C1 C2 . 1.482(6) ?
  C1 C6 . 1.498(6) ?
  C1 H1A . 0.9800 ?
  C2 C3 . 1.487(7) ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C3 C4 . 1.491(7) ?
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  C4 C5 . 1.455(7) ?
  C4 H4A . 0.9700 ?
  C4 H4B . 0.9700 ?
  C5 C6 . 1.503(7) ?
  C5 H5A . 0.9700 ?
  C5 H5B . 0.9700 ?
  C6 H6A . 0.9700 ?
  C6 H6B . 0.9700 ?
  C7 C12 . 1.530(5) ?
  C7 C8 . 1.532(5) ?
  C7 H7A . 0.9800 ?
  C8 C9 . 1.511(6) ?
  C8 H8A . 0.9700 ?
  C8 H8B . 0.9700 ?
  C9 C10 . 1.505(6) ?
  C9 H9A . 0.9700 ?
  C9 H9B . 0.9700 ?
  C10 C11 . 1.520(6) ?
  C10 H10A . 0.9700 ?
  C10 H10B . 0.9700 ?
  C11 C12 . 1.521(6) ?
  C11 H11A . 0.9700 ?
  C11 H11B . 0.9700 ?
  C12 H12A . 0.9700 ?
  C12 H12B . 0.9700 ?
  C13 C17 . 1.349(5) ?
  C13 C14 . 1.378(5) ?
  C14 C15 . 1.396(6) ?
  C16 C17 . 1.393(6) ?
  C17 H17A . 0.9300 ?
  C18 H18A . 0.9600 ?
  C18 H18B . 0.9600 ?
  C18 H18C . 0.9600 ?
  C19 H19A . 0.9600 ?
  C19 H19B . 0.9600 ?
  C19 H19C . 0.9600 ?
  Br2 C33 . 1.892(4) ?
  P2 O4 . 1.482(3) ?
  P2 C26 . 1.810(4) ?
  P2 C20 . 1.828(4) ?
  P2 C32 . 1.853(4) ?
  O5 C34 . 1.347(5) ?
  O5 C37 . 1.440(5) ?
  O6 C35 . 1.355(5) ?
  O6 C38 . 1.410(5) ?
  N2 C35 . 1.323(5) ?
  N2 C34 . 1.323(5) ?
  C20 C21 . 1.509(6) ?
  C20 C25 . 1.527(6) ?
  C20 H20A . 0.9800 ?
  C21 C22 . 1.516(6) ?
  C21 H21A . 0.9700 ?
  C21 H21B . 0.9700 ?
  C22 C23 . 1.517(7) ?
  C22 H22A . 0.9700 ?
  C22 H22B . 0.9700 ?
  C23 C24 . 1.497(8) ?
  C23 H23A . 0.9700 ?
  C23 H23B . 0.9700 ?
  C24 C25 . 1.519(7) ?
  C24 H24A . 0.9700 ?
  C24 H24B . 0.9700 ?
  C25 H25A . 0.9700 ?
  C25 H25B . 0.9700 ?
  C26 C27 . 1.518(5) ?
  C26 C31 . 1.520(5) ?
  C26 H26A . 0.9800 ?
  C27 C28 . 1.533(6) ?
  C27 H27A . 0.9700 ?
  C27 H27B . 0.9700 ?
  C28 C29 . 1.520(6) ?
  C28 H28A . 0.9700 ?
  C28 H28B . 0.9700 ?
  C29 C30 . 1.528(6) ?
  C29 H29A . 0.9700 ?
  C29 H29B . 0.9700 ?
  C30 C31 . 1.512(6) ?
  C30 H30A . 0.9700 ?
  C30 H30B . 0.9700 ?
  C31 H31A . 0.9700 ?
  C31 H31B . 0.9700 ?
  C32 C33 . 1.384(5) ?
  C32 C36 . 1.389(5) ?
  C33 C34 . 1.385(5) ?
  C35 C36 . 1.374(5) ?
  C36 H36A . 0.9300 ?
  C37 H37A . 0.9600 ?
  C37 H37B . 0.9600 ?
  C37 H37C . 0.9600 ?
  C38 H38A . 0.9600 ?
  C38 H38B . 0.9600 ?
  C38 H38C . 0.9600 ?
_cod_database_code 2202226