#------------------------------------------------------------------------------
#$Date: 2017-05-06 00:42:53 +0300 (Sat, 06 May 2017) $
#$Revision: 196324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/55/1545531.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_1545531
loop_
_publ_author_name
'Hansmann, Max M.'
'Ruiz, David A.'
'Liu, Liu (Leo)'
'Jazzar, Rodolphe'
'Bertrand, Guy'
_publ_section_title
;
 (Phosphanyl)phosphaketenes as building blocks for novel phosphorus
 heterocycles
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              3720
_journal_paper_doi               10.1039/C7SC00300E
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         'C38 H53 N3 O P2'
_chemical_formula_sum            'C38 H53 N3 O P2'
_chemical_formula_weight         629.77
_chemical_name_systematic        AdamPPCO
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.09 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-01-19 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.5089(11)
_cell_length_b                   17.8123(9)
_cell_length_c                   9.2449(5)
_cell_measurement_reflns_used    4622
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      25.44
_cell_measurement_theta_min      2.29
_cell_volume                     3541.9(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24783
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.495
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_min         2.287
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0641 before and 0.0573 after correction. The Ratio of minimum to maximum transmission is 0.8045. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0411P)²+3.4855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1140
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2589
_reflns_number_total             3402
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7sc00300e2.cif
_cod_data_source_block           liu
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1545527--1545532.cif.
;
_cod_database_code               1545531
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H22A(0.5) H22B(0.5)
3.a Ternary CH refined with riding coordinates:
 C13(H13), C6(H6), C21(H21), C18(H18)
3.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C17(H17A,H17B), C20(H20A,H20B), C3(H3A,H3B), C19(H19A,H19B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
P1 P 0.53688(4) 0.250000 0.63494(8) 0.00881(19) Uani 1 2 d S T P
P2 P 0.46769(4) 0.250000 0.47424(9) 0.0166(2) Uani 1 2 d S T P
O1 O 0.54499(10) 0.250000 0.2345(2) 0.0192(5) Uani 1 2 d S T P
N1 N 0.54540(8) 0.31817(9) 0.75576(19) 0.0107(4) Uani 1 1 d . . .
N2 N 0.64946(12) 0.250000 0.4897(3) 0.0140(6) Uani 1 2 d S T P
C4 C 0.53076(10) 0.39612(11) 0.7309(2) 0.0105(4) Uani 1 1 d . . .
C1 C 0.59075(14) 0.250000 0.4808(3) 0.0116(7) Uani 1 2 d S T P
C12 C 0.46897(10) 0.42072(12) 0.7457(2) 0.0136(5) Uani 1 1 d . . .
C5 C 0.57911(10) 0.44692(13) 0.6985(2) 0.0150(5) Uani 1 1 d . . .
C13 C 0.41674(10) 0.36859(13) 0.7929(3) 0.0168(5) Uani 1 1 d . . .
H13 H 0.432207 0.315791 0.785336 0.020 Uiso 1 1 calc R . .
C6 C 0.64688(10) 0.42275(14) 0.6944(3) 0.0183(5) Uani 1 1 d . . .
H6 H 0.648408 0.367615 0.674346 0.022 Uiso 1 1 calc R . .
C16 C 0.69342(13) 0.250000 0.3653(3) 0.0120(6) Uani 1 2 d S T P
C2 C 0.53913(14) 0.250000 0.3662(4) 0.0138(7) Uani 1 2 d S T P
C22 C 0.75836(13) 0.250000 0.4338(4) 0.0144(7) Uani 1 2 d S T P
H22A H 0.763220 0.205007 0.495605 0.017 Uiso 0.5 1 calc R . .
H22B H 0.763220 0.294993 0.495605 0.017 Uiso 0.5 1 calc R . .
C21 C 0.80881(14) 0.250000 0.3159(4) 0.0167(7) Uani 1 2 d S T P
H21 H 0.850823 0.250002 0.362226 0.020 Uiso 1 2 calc RS T P
C9 C 0.56354(11) 0.52219(13) 0.6785(3) 0.0221(6) Uani 1 1 d . . .
H9 H 0.595334 0.557305 0.655900 0.027 Uiso 1 1 calc R . .
C17 C 0.68618(10) 0.17966(13) 0.2708(3) 0.0187(5) Uani 1 1 d . . .
H17A H 0.644529 0.179271 0.225256 0.022 Uiso 1 1 calc R . .
H17B H 0.690207 0.134057 0.331295 0.022 Uiso 1 1 calc R . .
C10 C 0.50313(11) 0.54667(14) 0.6907(3) 0.0238(6) Uani 1 1 d . . .
H10 H 0.493542 0.598109 0.675229 0.029 Uiso 1 1 calc R . .
C11 C 0.45633(11) 0.49669(13) 0.7255(3) 0.0209(6) Uani 1 1 d . . .
H11 H 0.414905 0.514414 0.735852 0.025 Uiso 1 1 calc R . .
C20 C 0.80141(10) 0.17960(14) 0.2234(3) 0.0225(6) Uani 1 1 d . . .
H20A H 0.806241 0.134293 0.284364 0.027 Uiso 1 1 calc R . .
H20B H 0.833896 0.178514 0.147523 0.027 Uiso 1 1 calc R . .
C18 C 0.73684(10) 0.17990(14) 0.1531(3) 0.0236(6) Uani 1 1 d . . .
H18 H 0.732145 0.134221 0.091128 0.028 Uiso 1 1 calc R . .
C7 C 0.68444(12) 0.46323(15) 0.5776(3) 0.0277(6) Uani 1 1 d . . .
H7A H 0.662954 0.458814 0.484463 0.042 Uiso 1 1 calc GR . .
H7B H 0.725788 0.440442 0.570146 0.042 Uiso 1 1 calc GR . .
H7C H 0.688644 0.516379 0.603172 0.042 Uiso 1 1 calc GR . .
C8 C 0.67736(11) 0.43707(18) 0.8417(3) 0.0329(7) Uani 1 1 d . . .
H8A H 0.678780 0.491203 0.860304 0.049 Uiso 1 1 calc GR . .
H8B H 0.719739 0.416854 0.841241 0.049 Uiso 1 1 calc GR . .
H8C H 0.653073 0.412311 0.917606 0.049 Uiso 1 1 calc GR . .
C14 C 0.35861(12) 0.37542(16) 0.6993(3) 0.0357(7) Uani 1 1 d . . .
H14A H 0.340101 0.425207 0.712794 0.054 Uiso 1 1 calc GR . .
H14B H 0.328546 0.336788 0.727658 0.054 Uiso 1 1 calc GR . .
H14C H 0.369852 0.368667 0.597438 0.054 Uiso 1 1 calc GR . .
C3 C 0.55806(15) 0.29071(14) 0.9014(3) 0.0349(7) Uani 1 1 d . . .
H3A H 0.598985 0.309489 0.934445 0.042 Uiso 1 1 calc R . .
H3B H 0.525889 0.309493 0.968850 0.042 Uiso 1 1 calc R . .
C19 C 0.73005(16) 0.250000 0.0594(4) 0.0301(9) Uani 1 2 d S T P
H19A H 0.762326 0.250000 -0.016899 0.036 Uiso 1 2 calc RS T P
H19B H 0.688798 0.250000 0.011944 0.036 Uiso 1 2 calc RS T P
C15 C 0.40103(14) 0.38380(18) 0.9511(3) 0.0412(8) Uani 1 1 d . . .
H15A H 0.438521 0.377859 1.010195 0.062 Uiso 1 1 calc GR . .
H15B H 0.369233 0.348185 0.983545 0.062 Uiso 1 1 calc GR . .
H15C H 0.385235 0.435149 0.961082 0.062 Uiso 1 1 calc GR . .
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'
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
N1 P1 P2 123.61(6) 7_565 .
N1 P1 P2 123.61(6) . .
N1 P1 N1 94.02(13) 7_565 .
N1 P1 C1 116.89(9) 7_565 .
N1 P1 C1 116.89(9) . .
C1 P1 P2 84.17(10) . .
C2 P2 P1 77.96(11) . .
C4 N1 P1 124.97(14) . .
C4 N1 C3 120.71(17) . .
C3 N1 P1 113.36(14) . .
C1 N2 C16 125.7(3) . .
C12 C4 N1 119.41(18) . .
C12 C4 C5 121.16(19) . .
C5 C4 N1 119.37(18) . .
N2 C1 P1 125.4(2) . .
N2 C1 C2 140.1(3) . .
C2 C1 P1 94.5(2) . .
C4 C12 C13 122.38(19) . .
C11 C12 C4 118.3(2) . .
C11 C12 C13 119.2(2) . .
C4 C5 C6 122.0(2) . .
C9 C5 C4 117.9(2) . .
C9 C5 C6 120.0(2) . .
C12 C13 H13 107.9 . .
C12 C13 C14 113.2(2) . .
C12 C13 C15 109.3(2) . .
C14 C13 H13 107.9 . .
C15 C13 H13 107.9 . .
C15 C13 C14 110.4(2) . .
C5 C6 H6 108.3 . .
C5 C6 C7 113.0(2) . .
C5 C6 C8 109.94(19) . .
C7 C6 H6 108.3 . .
C7 C6 C8 108.8(2) . .
C8 C6 H6 108.3 . .
N2 C16 C22 105.0(2) . .
N2 C16 C17 112.03(16) . .
N2 C16 C17 112.03(16) . 7_565
C22 C16 C17 109.10(16) . 7_565
C22 C16 C17 109.10(16) . .
C17 C16 C17 109.4(3) . 7_565
O1 C2 P2 128.9(2) . .
O1 C2 C1 127.7(3) . .
C1 C2 P2 103.3(2) . .
C16 C22 H22A 109.6 . .
C16 C22 H22B 109.6 . .
C16 C22 C21 110.5(3) . .
H22A C22 H22B 108.1 . .
C21 C22 H22A 109.6 . .
C21 C22 H22B 109.6 . .
C22 C21 H21 109.5 . .
C20 C21 C22 108.88(17) . .
C20 C21 C22 108.88(17) 7_565 .
C20 C21 H21 109.5 7_565 .
C20 C21 H21 109.5 . .
C20 C21 C20 110.5(3) 7_565 .
C5 C9 H9 119.3 . .
C10 C9 C5 121.4(2) . .
C10 C9 H9 119.3 . .
C16 C17 H17A 109.8 . .
C16 C17 H17B 109.8 . .
C16 C17 C18 109.16(19) . .
H17A C17 H17B 108.3 . .
C18 C17 H17A 109.8 . .
C18 C17 H17B 109.8 . .
C9 C10 H10 119.9 . .
C9 C10 C11 120.2(2) . .
C11 C10 H10 119.9 . .
C12 C11 H11 119.5 . .
C10 C11 C12 121.0(2) . .
C10 C11 H11 119.5 . .
C21 C20 H20A 109.8 . .
C21 C20 H20B 109.8 . .
C21 C20 C18 109.2(2) . .
H20A C20 H20B 108.3 . .
C18 C20 H20A 109.8 . .
C18 C20 H20B 109.8 . .
C17 C18 H18 109.3 . .
C20 C18 C17 110.0(2) . .
C20 C18 H18 109.3 . .
C19 C18 C17 109.6(2) . .
C19 C18 C20 109.3(2) . .
C19 C18 H18 109.3 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C6 C8 H8A 109.5 . .
C6 C8 H8B 109.5 . .
C6 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N1 C3 H3A 109.7 . .
N1 C3 H3B 109.7 . .
C3 C3 N1 109.60(12) 7_565 .
C3 C3 H3A 109.7 7_565 .
C3 C3 H3B 109.7 7_565 .
H3A C3 H3B 108.2 . .
C18 C19 C18 109.8(3) 7_565 .
C18 C19 H19A 109.7 . .
C18 C19 H19A 109.7 7_565 .
C18 C19 H19B 109.7 7_565 .
C18 C19 H19B 109.7 . .
H19A C19 H19B 108.2 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 P2 2.1028(11) .
P1 N1 1.6601(18) 7_565
P1 N1 1.6601(18) .
P1 C1 1.837(3) .
P2 C2 1.832(3) .
O1 C2 1.225(4) .
N1 C4 1.442(3) .
N1 C3 1.458(3) .
N2 C1 1.265(4) .
N2 C16 1.489(4) .
C4 C12 1.406(3) .
C4 C5 1.411(3) .
C1 C2 1.535(4) .
C12 C13 1.522(3) .
C12 C11 1.393(3) .
C5 C6 1.520(3) .
C5 C9 1.394(3) .
C13 H13 1.0000 .
C13 C14 1.525(3) .
C13 C15 1.525(3) .
C6 H6 1.0000 .
C6 C7 1.530(3) .
C6 C8 1.532(3) .
C16 C22 1.534(4) .
C16 C17 1.535(3) .
C16 C17 1.535(3) 7_565
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C22 C21 1.538(4) .
C21 H21 1.0000 .
C21 C20 1.526(3) .
C21 C20 1.526(3) 7_565
C9 H9 0.9500 .
C9 C10 1.375(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C18 1.540(3) .
C10 H10 0.9500 .
C10 C11 1.382(3) .
C11 H11 0.9500 .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C20 C18 1.533(3) .
C18 H18 1.0000 .
C18 C19 1.526(3) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C3 C3 1.450(5) 7_565
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
