#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:24:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180077 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/23/7052387.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_7052387
loop_
_publ_author_name
'Matthieu Demange'
'Leila Boubekeur'
'Audrey Auffrant'
'Nicolas Mézailles'
'Louis Ricard'
'Xavier Le Goff'
'Pascal Le Floch'
_publ_section_title
;
 A new and convenient approach towards bis(iminophosphoranyl)methane
 ligands and their dicationic, cationic, anionic and dianionic
 derivatives
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1745
_journal_paper_doi               10.1039/b610049j
_journal_volume                  30
_journal_year                    2006
_chemical_formula_sum            'C39 H54 Br2 N2 O P2'
_chemical_formula_weight         788.60
_chemical_name_systematic
;
?
;
_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                   11.1170(10)
_cell_length_b                   18.7140(10)
_cell_length_c                   18.9410(10)
_cell_measurement_reflns_used    251
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      3.0
_cell_volume                     3940.6(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.0(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  KappaCCD
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12758
_diffrn_reflns_theta_full        27.14
_diffrn_reflns_theta_max         27.14
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    2.170
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_correction_T_min  0.6353
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.016(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         8375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0342
_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)+(0.0348P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0758
_reflns_number_gt                6923
_reflns_number_total             8375
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b610049j.txt
_cod_data_source_block           br2p2n2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P212121 '
_cod_database_code               7052387
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.29419(3) 0.304586(16) -0.018442(16) 0.03851(9) Uani 1 1 d . . .
Br2 Br 0.17011(3) -0.119712(16) 0.087207(16) 0.04090(9) Uani 1 1 d . . .
P1 P 0.15363(7) 0.10971(4) 0.11829(4) 0.02858(16) Uani 1 1 d . . .
P2 P 0.16607(7) 0.08058(4) -0.04538(4) 0.02845(16) Uani 1 1 d . . .
N1 N 0.0850(2) 0.03772(14) 0.14077(14) 0.0340(6) Uani 1 1 d . . .
H1 H 0.106(3) 0.0042(18) 0.1332(19) 0.041 Uiso 1 1 d . . .
N2 N 0.0974(2) 0.00423(14) -0.03897(13) 0.0322(6) Uani 1 1 d . . .
H2 H 0.103(3) -0.0156(17) -0.0047(18) 0.039 Uiso 1 1 d . . .
C1 C 0.1243(2) 0.13850(14) 0.02766(13) 0.0275(6) Uani 1 1 d . . .
H1A H 0.0369 0.1480 0.0237 0.033 Uiso 1 1 calc R . .
H1B H 0.1659 0.1847 0.0207 0.033 Uiso 1 1 calc R . .
C2 C 0.3117(3) 0.09645(15) 0.12980(14) 0.0311(7) Uani 1 1 d . . .
C3 C 0.3899(3) 0.15013(16) 0.10655(15) 0.0338(7) Uani 1 1 d . . .
H3 H 0.3595 0.1905 0.0820 0.041 Uiso 1 1 calc R . .
C4 C 0.5119(3) 0.14385(18) 0.11956(17) 0.0393(8) Uani 1 1 d . . .
H4 H 0.5659 0.1796 0.1034 0.047 Uiso 1 1 calc R . .
C5 C 0.5547(3) 0.08529(19) 0.15614(17) 0.0460(8) Uani 1 1 d . . .
H5 H 0.6383 0.0814 0.1657 0.055 Uiso 1 1 calc R . .
C6 C 0.4779(3) 0.03239(19) 0.17901(18) 0.0442(8) Uani 1 1 d . . .
H6 H 0.5095 -0.0079 0.2033 0.053 Uiso 1 1 calc R . .
C7 C 0.3555(3) 0.03706(16) 0.16707(16) 0.0360(7) Uani 1 1 d . . .
H7 H 0.3024 0.0010 0.1836 0.043 Uiso 1 1 calc R . .
C8 C 0.1067(3) 0.18027(15) 0.17632(15) 0.0325(7) Uani 1 1 d . . .
C9 C 0.1826(3) 0.19763(16) 0.23257(14) 0.0395(7) Uani 1 1 d . . .
H9 H 0.2607 0.1772 0.2353 0.047 Uiso 1 1 calc R . .
C10 C 0.1437(4) 0.24486(18) 0.28464(18) 0.0503(9) Uani 1 1 d . . .
H10 H 0.1959 0.2576 0.3223 0.060 Uiso 1 1 calc R . .
C11 C 0.0299(4) 0.27297(18) 0.28142(18) 0.0522(10) Uani 1 1 d . . .
H11 H 0.0022 0.3037 0.3179 0.063 Uiso 1 1 calc R . .
C12 C -0.0453(3) 0.25647(19) 0.22468(18) 0.0517(10) Uani 1 1 d . . .
H12 H -0.1233 0.2771 0.2220 0.062 Uiso 1 1 calc R . .
C13 C -0.0068(3) 0.21021(17) 0.17225(18) 0.0421(8) Uani 1 1 d . . .
H13 H -0.0581 0.1991 0.1337 0.051 Uiso 1 1 calc R . .
C14 C -0.0420(3) 0.02890(17) 0.16475(16) 0.0361(7) Uani 1 1 d . . .
H14 H -0.0739 0.0771 0.1777 0.043 Uiso 1 1 calc R . .
C15 C -0.0404(3) -0.01755(19) 0.23181(17) 0.0430(8) Uani 1 1 d . . .
H15 H 0.0033 -0.0629 0.2207 0.052 Uiso 1 1 calc R . .
C16 C -0.1190(3) -0.0006(2) 0.10511(17) 0.0492(9) Uani 1 1 d . . .
H16A H -0.1158 0.0320 0.0647 0.074 Uiso 1 1 calc R . .
H16B H -0.2024 -0.0052 0.1212 0.074 Uiso 1 1 calc R . .
H16C H -0.0885 -0.0476 0.0910 0.074 Uiso 1 1 calc R . .
C17 C 0.0268(4) 0.0202(2) 0.29017(18) 0.0648(12) Uani 1 1 d . . .
H17A H 0.1087 0.0311 0.2743 0.097 Uiso 1 1 calc R . .
H17B H 0.0303 -0.0107 0.3319 0.097 Uiso 1 1 calc R . .
H17C H -0.0149 0.0647 0.3022 0.097 Uiso 1 1 calc R . .
C18 C -0.1675(4) -0.0367(2) 0.2551(2) 0.0669(11) Uani 1 1 d . . .
H18A H -0.1642 -0.0627 0.3000 0.100 Uiso 1 1 calc R . .
H18B H -0.2053 -0.0670 0.2191 0.100 Uiso 1 1 calc R . .
H18C H -0.2147 0.0071 0.2610 0.100 Uiso 1 1 calc R . .
C19 C 0.3263(3) 0.07425(15) -0.04705(14) 0.0301(6) Uani 1 1 d . . .
C20 C 0.3964(3) 0.13144(16) -0.07102(15) 0.0339(7) Uani 1 1 d . . .
H20 H 0.3589 0.1726 -0.0904 0.041 Uiso 1 1 calc R . .
C21 C 0.5209(3) 0.12788(18) -0.06645(16) 0.0374(7) Uani 1 1 d . . .
H21 H 0.5691 0.1662 -0.0833 0.045 Uiso 1 1 calc R . .
C22 C 0.5739(3) 0.06839(18) -0.03728(16) 0.0407(8) Uani 1 1 d . . .
H22 H 0.6591 0.0663 -0.0338 0.049 Uiso 1 1 calc R . .
C23 C 0.5063(3) 0.01186(17) -0.01310(18) 0.0403(8) Uani 1 1 d . . .
H23 H 0.5447 -0.0286 0.0071 0.048 Uiso 1 1 calc R . .
C24 C 0.3817(3) 0.01414(15) -0.01827(15) 0.0334(7) Uani 1 1 d . . .
H24 H 0.3346 -0.0250 -0.0023 0.040 Uiso 1 1 calc R . .
C25 C 0.1115(3) 0.12134(16) -0.12461(15) 0.0309(6) Uani 1 1 d . . .
C26 C -0.0045(3) 0.14824(16) -0.12567(16) 0.0375(8) Uani 1 1 d . . .
H26 H -0.0501 0.1499 -0.0833 0.045 Uiso 1 1 calc R . .
C27 C -0.0545(3) 0.17284(18) -0.18818(17) 0.0471(9) Uani 1 1 d . . .
H27 H -0.1346 0.1906 -0.1887 0.057 Uiso 1 1 calc R . .
C28 C 0.0123(4) 0.17151(18) -0.24960(18) 0.0460(9) Uani 1 1 d . . .
H28 H -0.0219 0.1887 -0.2923 0.055 Uiso 1 1 calc R . .
C29 C 0.1284(3) 0.14539(17) -0.24942(16) 0.0426(8) Uani 1 1 d . . .
H29 H 0.1742 0.1449 -0.2918 0.051 Uiso 1 1 calc R . .
C30 C 0.1779(3) 0.12002(16) -0.18739(14) 0.0374(7) Uani 1 1 d . . .
H30 H 0.2575 0.1016 -0.1873 0.045 Uiso 1 1 calc R . .
C31 C 0.0738(3) -0.04375(16) -0.10048(15) 0.0356(7) Uani 1 1 d . . .
H31 H 0.0657 -0.0129 -0.1433 0.043 Uiso 1 1 calc R . .
C32 C -0.0467(3) -0.08104(16) -0.08907(18) 0.0413(8) Uani 1 1 d . . .
H32 H -0.0442 -0.1056 -0.0422 0.050 Uiso 1 1 calc R . .
C33 C 0.1797(3) -0.09427(19) -0.11302(18) 0.0537(9) Uani 1 1 d . . .
H33A H 0.2532 -0.0663 -0.1204 0.081 Uiso 1 1 calc R . .
H33B H 0.1639 -0.1236 -0.1549 0.081 Uiso 1 1 calc R . .
H33C H 0.1900 -0.1253 -0.0718 0.081 Uiso 1 1 calc R . .
C34 C -0.1477(3) -0.0274(2) -0.0877(2) 0.0546(9) Uani 1 1 d . . .
H34A H -0.1548 -0.0047 -0.1341 0.082 Uiso 1 1 calc R . .
H34B H -0.1307 0.0091 -0.0520 0.082 Uiso 1 1 calc R . .
H34C H -0.2232 -0.0517 -0.0761 0.082 Uiso 1 1 calc R . .
C35 C -0.0703(4) -0.1376(2) -0.1461(2) 0.0650(11) Uani 1 1 d . . .
H35A H -0.1519 -0.1566 -0.1405 0.098 Uiso 1 1 calc R . .
H35B H -0.0119 -0.1765 -0.1413 0.098 Uiso 1 1 calc R . .
H35C H -0.0623 -0.1157 -0.1929 0.098 Uiso 1 1 calc R . .
O1 O 0.1008(6) -0.3045(11) -0.0797(5) 0.086(4) Uani 0.77(4) 1 d P A 1
O1A O 0.102(3) -0.3397(19) -0.0621(15) 0.078(7) Uani 0.23(4) 1 d P A 2
C36 C 0.1823(4) -0.3065(3) -0.0204(2) 0.0765(12) Uani 1 1 d . . .
H36A H 0.2294 -0.2617 -0.0186 0.092 Uiso 0.77(4) 1 calc PR A 1
H36B H 0.2391 -0.3469 -0.0259 0.092 Uiso 0.77(4) 1 calc PR A 1
H36C H 0.1941 -0.2557 -0.0334 0.092 Uiso 0.23(4) 1 calc PR A 2
H36D H 0.2608 -0.3315 -0.0190 0.092 Uiso 0.23(4) 1 calc PR A 2
C37 C 0.1121(4) -0.3153(2) 0.0466(2) 0.0627(11) Uani 1 1 d . A .
H37A H 0.1413 -0.2822 0.0836 0.075 Uiso 1 1 calc R . .
H37B H 0.1171 -0.3649 0.0643 0.075 Uiso 1 1 calc R . .
C38 C -0.0145(4) -0.2969(2) 0.0245(2) 0.0704(12) Uani 1 1 d . . .
H38A H -0.0741 -0.3261 0.0504 0.084 Uiso 1 1 calc R A .
H38B H -0.0319 -0.2457 0.0324 0.084 Uiso 1 1 calc R . .
C39 C -0.0147(4) -0.3146(3) -0.0526(2) 0.0733(13) Uani 1 1 d . A .
H39A H -0.0398 -0.3649 -0.0595 0.088 Uiso 0.77(4) 1 calc PR A 1
H39B H -0.0725 -0.2834 -0.0777 0.088 Uiso 0.77(4) 1 calc PR A 1
H39C H -0.0750 -0.3519 -0.0638 0.088 Uiso 0.23(4) 1 calc PR A 2
H39D H -0.0305 -0.2718 -0.0818 0.088 Uiso 0.23(4) 1 calc PR A 2
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 C2 108.57(14) . . ?
N1 P1 C8 108.44(14) . . ?
C2 P1 C8 108.26(14) . . ?
N1 P1 C1 114.29(14) . . ?
C2 P1 C1 109.30(13) . . ?
C8 P1 C1 107.82(13) . . ?
N2 P2 C19 114.31(14) . . ?
N2 P2 C25 106.18(14) . . ?
C19 P2 C25 110.58(13) . . ?
N2 P2 C1 110.33(13) . . ?
C19 P2 C1 107.94(13) . . ?
C25 P2 C1 107.31(13) . . ?
C14 N1 P1 128.6(2) . . ?
C31 N2 P2 123.6(2) . . ?
P2 C1 P1 119.55(15) . . ?
C3 C2 C7 120.8(3) . . ?
C3 C2 P1 118.2(2) . . ?
C7 C2 P1 120.8(2) . . ?
C4 C3 C2 119.5(3) . . ?
C5 C4 C3 119.6(3) . . ?
C6 C5 C4 121.0(3) . . ?
C5 C6 C7 120.9(3) . . ?
C6 C7 C2 118.3(3) . . ?
C13 C8 C9 119.9(3) . . ?
C13 C8 P1 122.0(2) . . ?
C9 C8 P1 117.5(2) . . ?
C10 C9 C8 120.0(3) . . ?
C11 C10 C9 119.9(3) . . ?
C10 C11 C12 120.1(3) . . ?
C13 C12 C11 120.3(3) . . ?
C8 C13 C12 119.7(3) . . ?
N1 C14 C16 110.3(3) . . ?
N1 C14 C15 107.6(3) . . ?
C16 C14 C15 114.5(3) . . ?
C17 C15 C18 111.0(3) . . ?
C17 C15 C14 110.2(3) . . ?
C18 C15 C14 111.2(3) . . ?
C24 C19 C20 119.9(3) . . ?
C24 C19 P2 119.2(2) . . ?
C20 C19 P2 120.7(2) . . ?
C21 C20 C19 119.9(3) . . ?
C22 C21 C20 119.4(3) . . ?
C21 C22 C23 121.4(3) . . ?
C22 C23 C24 119.9(3) . . ?
C23 C24 C19 119.5(3) . . ?
C26 C25 C30 119.0(3) . . ?
C26 C25 P2 118.9(2) . . ?
C30 C25 P2 121.7(2) . . ?
C25 C26 C27 120.4(3) . . ?
C28 C27 C26 119.9(3) . . ?
C29 C28 C27 120.5(3) . . ?
C28 C29 C30 119.7(3) . . ?
C29 C30 C25 120.4(3) . . ?
N2 C31 C32 108.6(2) . . ?
N2 C31 C33 110.9(3) . . ?
C32 C31 C33 114.5(3) . . ?
C34 C32 C31 110.6(3) . . ?
C34 C32 C35 110.1(3) . . ?
C31 C32 C35 111.5(3) . . ?
C39 O1 C36 106.8(8) . . ?
C36 O1A C39 112.9(16) . . ?
O1A C36 O1 30.4(10) . . ?
O1A C36 C37 95.7(15) . . ?
O1 C36 C37 109.5(4) . . ?
C36 C37 C38 103.1(3) . . ?
C39 C38 C37 102.8(4) . . ?
O1A C39 O1 30.7(10) . . ?
O1A C39 C38 101.6(11) . . ?
O1 C39 C38 109.1(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N1 1.606(3) . ?
P1 C2 1.788(3) . ?
P1 C8 1.796(3) . ?
P1 C1 1.828(3) . ?
P2 N2 1.624(3) . ?
P2 C19 1.786(3) . ?
P2 C25 1.789(3) . ?
P2 C1 1.818(3) . ?
N1 C14 1.492(4) . ?
N2 C31 1.494(4) . ?
C2 C3 1.400(4) . ?
C2 C7 1.404(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.381(5) . ?
C5 C6 1.377(5) . ?
C6 C7 1.382(4) . ?
C8 C13 1.382(5) . ?
C8 C9 1.397(4) . ?
C9 C10 1.393(4) . ?
C10 C11 1.372(5) . ?
C11 C12 1.396(5) . ?
C12 C13 1.385(5) . ?
C14 C16 1.521(5) . ?
C14 C15 1.539(4) . ?
C15 C17 1.510(5) . ?
C15 C18 1.523(5) . ?
C19 C24 1.393(4) . ?
C19 C20 1.400(4) . ?
C20 C21 1.389(4) . ?
C21 C22 1.375(5) . ?
C22 C23 1.377(5) . ?
C23 C24 1.389(4) . ?
C25 C26 1.384(4) . ?
C25 C30 1.400(4) . ?
C26 C27 1.387(4) . ?
C27 C28 1.381(5) . ?
C28 C29 1.380(5) . ?
C29 C30 1.381(4) . ?
C31 C32 1.526(4) . ?
C31 C33 1.529(5) . ?
C32 C34 1.507(5) . ?
C32 C35 1.534(5) . ?
O1 C39 1.395(9) . ?
O1 C36 1.443(11) . ?
O1A C36 1.35(3) . ?
O1A C39 1.39(3) . ?
C36 C37 1.499(6) . ?
C37 C38 1.507(6) . ?
C38 C39 1.496(6) . ?
