#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:52:01 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179132 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/94/4309486.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_4309486
loop_
_publ_author_name
'Matthew C. Crowe'
'Ramesh N. Kapoor'
'Francisco Cervantes-Lee'
'Laszlo Párkányí'
'Louis Schulte'
'Keith H. Pannell'
'Jennifer S. Brodbelt'
_publ_section_title
;
Investigating Bidentate and Tridentate Carbamoylmethylphosphine Oxide
Ligand Interactions with Rare-Earth Elements Using Electrospray Ionization
Quadrupole Ion Trap Mass Spectrometry
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6415
_journal_page_last               6424
_journal_paper_doi               10.1021/ic0503028
_journal_volume                  44
_journal_year                    2005
_chemical_formula_sum            'C40 H65 N2 O3 P'
_chemical_formula_weight         652.91
_chemical_name_common            'Carbamoylmethylphosphine Oxide'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.155(3)
_cell_angle_beta                 112.198(3)
_cell_angle_gamma                107.304(3)
_cell_formula_units_Z            2
_cell_length_a                   13.251(2)
_cell_length_b                   13.426(2)
_cell_length_c                   13.845(2)
_cell_measurement_reflns_used    99
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     1992.0(5)
_computing_cell_refinement       'Bruker SMART V5.625, 2001'
_computing_data_collection       'Bruker SMART V5.625, 2001'
_computing_data_reduction        'Bruker SAINT V5.622, 2001'
_computing_molecular_graphics    'Bruker SHELXTL V6.1012, 2000'
_computing_publication_material  'Bruker SHELXTL V6.1012, 2000'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.735
_diffrn_measured_fraction_theta_max 0.735
_diffrn_measurement_device_type  'CCD area detector'
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23236
_diffrn_reflns_theta_full        28.42
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9772
_exptl_absorpt_correction_T_min  0.9671
_exptl_absorpt_correction_type   'multi-scan (SADABS)'
_exptl_absorpt_process_details   'Bruker SADABS program (Sheldrick, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.088
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         7378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0688
_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)+(0.0626P)²+0.5328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1514
_reflns_number_gt                6116
_reflns_number_total             7378
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0503028si20050622_122730.cif
_cod_data_source_block           l952rk1m
_cod_original_cell_volume        1992.1(6)
_cod_database_code               4309486
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.89748(5) 0.77152(4) 0.99398(4) 0.01342(14) Uani 1 1 d . . .
O1 O 0.84494(13) 0.85325(12) 1.01235(13) 0.0202(3) Uani 1 1 d . . .
O2 O 0.99414(13) 0.63398(13) 0.86170(13) 0.0210(3) Uani 1 1 d . . .
O2' O 0.76477(15) 0.69667(14) 0.61597(13) 0.0328(4) Uani 1 1 d . . .
N1 N 0.80018(16) 0.50902(14) 0.73396(15) 0.0185(4) Uani 1 1 d . . .
N1' N 0.93723(16) 0.83692(15) 0.65423(15) 0.0193(4) Uani 1 1 d . . .
C1 C 0.85232(18) 0.71135(16) 0.84135(17) 0.0149(4) Uani 1 1 d . . .
H1 H 0.7627 0.6823 0.7954 0.018 Uiso 1 1 calc R . .
C2 C 0.88630(19) 0.61405(17) 0.81178(17) 0.0159(4) Uani 1 1 d . . .
C3 C 0.8415(2) 0.42035(18) 0.7114(2) 0.0235(5) Uani 1 1 d . . .
H3A H 0.7702 0.3451 0.6683 0.028 Uiso 1 1 calc R . .
H3B H 0.8944 0.4215 0.7852 0.028 Uiso 1 1 calc R . .
C4 C 0.9103(2) 0.4320(2) 0.6448(2) 0.0308(6) Uani 1 1 d . . .
H4 H 0.9834 0.5071 0.6903 0.037 Uiso 1 1 calc R . .
C5 C 0.9537(3) 0.3385(3) 0.6332(3) 0.0454(7) Uani 1 1 d . . .
H5A H 1.0027 0.3428 0.7091 0.068 Uiso 1 1 calc R . .
H5B H 1.0026 0.3488 0.5951 0.068 Uiso 1 1 calc R . .
H5C H 0.8836 0.2637 0.5881 0.068 Uiso 1 1 calc R . .
C6 C 0.8348(3) 0.4310(3) 0.5302(2) 0.0425(7) Uani 1 1 d . . .
H6A H 0.7609 0.3592 0.4849 0.064 Uiso 1 1 calc R . .
H6B H 0.8815 0.4381 0.4896 0.064 Uiso 1 1 calc R . .
H6C H 0.8133 0.4951 0.5419 0.064 Uiso 1 1 calc R . .
C7 C 0.67165(19) 0.48226(18) 0.66686(18) 0.0203(5) Uani 1 1 d . . .
H7A H 0.6352 0.4156 0.5943 0.024 Uiso 1 1 calc R . .
H7B H 0.6666 0.5476 0.6477 0.024 Uiso 1 1 calc R . .
C8 C 0.5968(2) 0.45646(19) 0.7259(2) 0.0237(5) Uani 1 1 d . . .
H8 H 0.6403 0.5193 0.8036 0.028 Uiso 1 1 calc R . .
C9 C 0.4748(2) 0.4560(2) 0.6592(3) 0.0398(7) Uani 1 1 d . . .
H9A H 0.4875 0.5320 0.6601 0.060 Uiso 1 1 calc R . .
H9B H 0.4245 0.4354 0.6943 0.060 Uiso 1 1 calc R . .
H9C H 0.4342 0.4003 0.5802 0.060 Uiso 1 1 calc R . .
C10 C 0.5807(2) 0.3446(2) 0.7398(2) 0.0310(6) Uani 1 1 d . . .
H10D H 0.5347 0.3329 0.7806 0.046 Uiso 1 1 calc R . .
H10E H 0.6603 0.3475 0.7834 0.046 Uiso 1 1 calc R . .
H10F H 0.5368 0.2815 0.6645 0.046 Uiso 1 1 calc R . .
C1' C 0.9146(2) 0.80636(17) 0.81209(18) 0.0187(4) Uani 1 1 d . . .
H2A H 0.9047 0.8748 0.8450 0.022 Uiso 1 1 calc R . .
H2B H 1.0023 0.8267 0.8481 0.022 Uiso 1 1 calc R . .
C2' C 0.8657(2) 0.77415(18) 0.68588(18) 0.0207(5) Uani 1 1 d . . .
C3' C 0.8893(2) 0.8101(2) 0.53176(19) 0.0249(5) Uani 1 1 d . . .
H3'A H 0.8504 0.7263 0.4895 0.030 Uiso 1 1 calc R . .
H3'B H 0.9576 0.8421 0.5180 0.030 Uiso 1 1 calc R . .
C4' C 0.7976(2) 0.8560(2) 0.4841(2) 0.0296(6) Uani 1 1 d . . .
H4' H 0.7249 0.8164 0.4904 0.035 Uiso 1 1 calc R . .
C5' C 0.7584(2) 0.8251(3) 0.3579(2) 0.0431(7) Uani 1 1 d . . .
H5'A H 0.6945 0.8484 0.3245 0.065 Uiso 1 1 calc R . .
H5'B H 0.7276 0.7425 0.3185 0.065 Uiso 1 1 calc R . .
H5'C H 0.8278 0.8645 0.3495 0.065 Uiso 1 1 calc R . .
C6' C 0.8455(3) 0.9835(2) 0.5487(3) 0.0401(7) Uani 1 1 d . . .
H6'A H 0.9183 1.0241 0.5456 0.060 Uiso 1 1 calc R . .
H6'B H 0.8654 1.0001 0.6284 0.060 Uiso 1 1 calc R . .
H6'C H 0.7836 1.0084 0.5139 0.060 Uiso 1 1 calc R . .
C7' C 1.05720(19) 0.93198(18) 0.73519(19) 0.0196(5) Uani 1 1 d . . .
H7'A H 1.0538 0.9750 0.8022 0.023 Uiso 1 1 calc R . .
H7'B H 1.0762 0.9842 0.6985 0.023 Uiso 1 1 calc R . .
C8' C 1.1603(2) 0.8965(2) 0.7770(2) 0.0265(5) Uani 1 1 d . . .
H8' H 1.1453 0.8512 0.8217 0.032 Uiso 1 1 calc R . .
C9' C 1.2789(2) 1.0040(2) 0.8568(2) 0.0324(6) Uani 1 1 d . . .
H9'A H 1.2959 1.0493 0.8144 0.049 Uiso 1 1 calc R . .
H9'B H 1.3449 0.9825 0.8881 0.049 Uiso 1 1 calc R . .
H9'C H 1.2720 1.0491 0.9193 0.049 Uiso 1 1 calc R . .
C10' C 1.1670(3) 0.8228(3) 0.6790(2) 0.0405(7) Uani 1 1 d . . .
H10A H 1.1778 0.8644 0.6318 0.061 Uiso 1 1 calc R . .
H10B H 1.0918 0.7522 0.6325 0.061 Uiso 1 1 calc R . .
H10C H 1.2355 0.8044 0.7095 0.061 Uiso 1 1 calc R . .
C1P C 1.06049(18) 0.84129(16) 1.07854(17) 0.0149(4) Uani 1 1 d . . .
C2P C 1.12166(19) 0.94193(17) 1.07209(18) 0.0186(4) Uani 1 1 d . . .
H2P H 1.0775 0.9665 1.0189 0.022 Uiso 1 1 calc R . .
C3P C 1.24448(19) 1.00619(17) 1.14110(18) 0.0191(4) Uani 1 1 d . . .
H3P H 1.2833 1.0736 1.1336 0.023 Uiso 1 1 calc R . .
C4P C 1.31317(19) 0.97514(18) 1.22137(18) 0.0196(5) Uani 1 1 d . . .
C5P C 1.2516(2) 0.87462(19) 1.2276(2) 0.0249(5) Uani 1 1 d . . .
H5P H 1.2958 0.8507 1.2815 0.030 Uiso 1 1 calc R . .
C6P C 1.1285(2) 0.80892(18) 1.15801(18) 0.0214(5) Uani 1 1 d . . .
H6P H 1.0899 0.7408 1.1645 0.026 Uiso 1 1 calc R . .
C7P C 0.84094(18) 0.65285(17) 1.02842(17) 0.0149(4) Uani 1 1 d . . .
C8P C 0.7562(2) 0.65105(18) 1.06489(18) 0.0196(5) Uani 1 1 d . . .
H8P H 0.7352 0.7131 1.0757 0.023 Uiso 1 1 calc R . .
C9P C 0.7024(2) 0.55952(19) 1.0854(2) 0.0231(5) Uani 1 1 d . . .
H9P H 0.6446 0.5600 1.1101 0.028 Uiso 1 1 calc R . .
C10P C 0.72995(19) 0.46639(18) 1.07112(18) 0.0202(5) Uani 1 1 d . . .
C11P C 0.81746(19) 0.47026(18) 1.03721(18) 0.0185(4) Uani 1 1 d . . .
H11P H 0.8400 0.4091 1.0286 0.022 Uiso 1 1 calc R . .
C12P C 0.87187(19) 0.56153(17) 1.01599(17) 0.0168(4) Uani 1 1 d . . .
H12P H 0.9308 0.5620 0.9927 0.020 Uiso 1 1 calc R . .
C1T C 1.4485(2) 1.0501(2) 1.3026(2) 0.0258(5) Uani 1 1 d . . .
C2T C 1.5186(2) 0.9778(3) 1.3100(3) 0.0445(7) Uani 1 1 d . . .
H2TA H 1.4901 0.9222 1.3392 0.067 Uiso 1 1 calc R . .
H2TB H 1.6051 1.0272 1.3615 0.067 Uiso 1 1 calc R . .
H2TC H 1.5058 0.9376 1.2340 0.067 Uiso 1 1 calc R . .
C3T C 1.5012(2) 1.1411(3) 1.2653(3) 0.0529(9) Uani 1 1 d . . .
H3TA H 1.4895 1.1045 1.1889 0.079 Uiso 1 1 calc R . .
H3TB H 1.5878 1.1865 1.3192 0.079 Uiso 1 1 calc R . .
H3TC H 1.4601 1.1910 1.2638 0.079 Uiso 1 1 calc R . .
C4T C 1.4646(3) 1.1095(3) 1.4205(3) 0.0556(9) Uani 1 1 d . . .
H4TA H 1.4221 1.1582 1.4162 0.083 Uiso 1 1 calc R . .
H4TB H 1.5509 1.1564 1.4749 0.083 Uiso 1 1 calc R . .
H4TC H 1.4310 1.0521 1.4458 0.083 Uiso 1 1 calc R . .
C5T C 0.6679(2) 0.3659(2) 1.0945(2) 0.0261(5) Uani 1 1 d . . .
C6T C 0.5310(2) 0.3286(2) 1.0369(3) 0.0398(7) Uani 1 1 d . . .
H6TA H 0.5144 0.3912 1.0700 0.060 Uiso 1 1 calc R . .
H6TB H 0.4918 0.2620 1.0489 0.060 Uiso 1 1 calc R . .
H6TC H 0.4992 0.3089 0.9549 0.060 Uiso 1 1 calc R . .
C7T C 0.6916(3) 0.2634(2) 1.0507(3) 0.0418(7) Uani 1 1 d . . .
H7TA H 0.6481 0.2001 1.0644 0.063 Uiso 1 1 calc R . .
H7TB H 0.7785 0.2848 1.0911 0.063 Uiso 1 1 calc R . .
H7TC H 0.6633 0.2399 0.9688 0.063 Uiso 1 1 calc R . .
C8T C 0.7182(3) 0.4052(2) 1.2234(2) 0.0399(7) Uani 1 1 d . . .
H8TA H 0.7078 0.4734 1.2530 0.060 Uiso 1 1 calc R . .
H8TB H 0.8044 0.4230 1.2601 0.060 Uiso 1 1 calc R . .
H8TC H 0.6746 0.3443 1.2397 0.060 Uiso 1 1 calc R . .
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
_geom_angle_publ_flag
O1 P1 C7P 112.42(9) . . ?
O1 P1 C1P 111.00(9) . . ?
C7P P1 C1P 108.43(9) . . ?
O1 P1 C1 108.31(9) . . ?
C7P P1 C1 106.68(9) . . ?
C1P P1 C1 109.89(9) . . ?
C2 N1 C3 116.48(18) . . ?
C2 N1 C7 123.80(18) . . ?
C3 N1 C7 119.57(17) . . ?
C2' N1' C7' 123.72(18) . . ?
C2' N1' C3' 117.36(18) . . ?
C7' N1' C3' 118.89(17) . . ?
C2 C1 C1' 109.70(17) . . ?
C2 C1 P1 111.76(14) . . ?
C1' C1 P1 108.64(13) . . ?
C2 C1 H1 108.9 . . ?
C1' C1 H1 108.9 . . ?
P1 C1 H1 108.9 . . ?
O2 C2 N1 121.61(19) . . ?
O2 C2 C1 118.02(18) . . ?
N1 C2 C1 120.37(18) . . ?
N1 C3 C4 114.88(19) . . ?
N1 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
N1 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C6 C4 C3 111.7(2) . . ?
C6 C4 C5 112.3(2) . . ?
C3 C4 C5 109.3(2) . . ?
C6 C4 H4 107.8 . . ?
C3 C4 H4 107.8 . . ?
C5 C4 H4 107.8 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C8 114.88(18) . . ?
N1 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
N1 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C10 112.3(2) . . ?
C7 C8 C9 109.0(2) . . ?
C10 C8 C9 111.2(2) . . ?
C7 C8 H8 108.1 . . ?
C10 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10D 109.5 . . ?
C8 C10 H10E 109.5 . . ?
H10D C10 H10E 109.5 . . ?
C8 C10 H10F 109.5 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
C2' C1' C1 113.52(17) . . ?
C2' C1' H2A 108.9 . . ?
C1 C1' H2A 108.9 . . ?
C2' C1' H2B 108.9 . . ?
C1 C1' H2B 108.9 . . ?
H2A C1' H2B 107.7 . . ?
O2' C2' N1' 122.0(2) . . ?
O2' C2' C1' 121.6(2) . . ?
N1' C2' C1' 116.41(19) . . ?
N1' C3' C4' 114.1(2) . . ?
N1' C3' H3'A 108.7 . . ?
C4' C3' H3'A 108.7 . . ?
N1' C3' H3'B 108.7 . . ?
C4' C3' H3'B 108.7 . . ?
H3'A C3' H3'B 107.6 . . ?
C6' C4' C5' 111.4(2) . . ?
C6' C4' C3' 113.0(2) . . ?
C5' C4' C3' 108.5(2) . . ?
C6' C4' H4' 107.9 . . ?
C5' C4' H4' 107.9 . . ?
C3' C4' H4' 107.9 . . ?
C4' C5' H5'A 109.5 . . ?
C4' C5' H5'B 109.5 . . ?
H5'A C5' H5'B 109.5 . . ?
C4' C5' H5'C 109.5 . . ?
H5'A C5' H5'C 109.5 . . ?
H5'B C5' H5'C 109.5 . . ?
C4' C6' H6'A 109.5 . . ?
C4' C6' H6'B 109.5 . . ?
H6'A C6' H6'B 109.5 . . ?
C4' C6' H6'C 109.5 . . ?
H6'A C6' H6'C 109.5 . . ?
H6'B C6' H6'C 109.5 . . ?
N1' C7' C8' 114.74(18) . . ?
N1' C7' H7'A 108.6 . . ?
C8' C7' H7'A 108.6 . . ?
N1' C7' H7'B 108.6 . . ?
C8' C7' H7'B 108.6 . . ?
H7'A C7' H7'B 107.6 . . ?
C10' C8' C9' 111.5(2) . . ?
C10' C8' C7' 112.3(2) . . ?
C9' C8' C7' 108.6(2) . . ?
C10' C8' H8' 108.1 . . ?
C9' C8' H8' 108.1 . . ?
C7' C8' H8' 108.1 . . ?
C8' C9' H9'A 109.5 . . ?
C8' C9' H9'B 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
C8' C9' H9'C 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C8' C10' H10A 109.5 . . ?
C8' C10' H10B 109.5 . . ?
H10A C10' H10B 109.5 . . ?
C8' C10' H10C 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?
C6P C1P C2P 117.37(19) . . ?
C6P C1P P1 124.78(16) . . ?
C2P C1P P1 117.51(15) . . ?
C3P C2P C1P 121.44(19) . . ?
C3P C2P H2P 119.3 . . ?
C1P C2P H2P 119.3 . . ?
C2P C3P C4P 121.7(2) . . ?
C2P C3P H3P 119.2 . . ?
C4P C3P H3P 119.2 . . ?
C3P C4P C5P 116.6(2) . . ?
C3P C4P C1T 121.7(2) . . ?
C5P C4P C1T 121.6(2) . . ?
C6P C5P C4P 122.1(2) . . ?
C6P C5P H5P 118.9 . . ?
C4P C5P H5P 118.9 . . ?
C5P C6P C1P 120.7(2) . . ?
C5P C6P H6P 119.6 . . ?
C1P C6P H6P 119.6 . . ?
C8P C7P C12P 118.43(19) . . ?
C8P C7P P1 116.69(16) . . ?
C12P C7P P1 124.81(16) . . ?
C9P C8P C7P 120.3(2) . . ?
C9P C8P H8P 119.9 . . ?
C7P C8P H8P 119.9 . . ?
C8P C9P C10P 122.2(2) . . ?
C8P C9P H9P 118.9 . . ?
C10P C9P H9P 118.9 . . ?
C9P C10P C11P 117.09(19) . . ?
C9P C10P C5T 120.7(2) . . ?
C11P C10P C5T 122.2(2) . . ?
C12P C11P C10P 121.3(2) . . ?
C12P C11P H11P 119.4 . . ?
C10P C11P H11P 119.4 . . ?
C11P C12P C7P 120.7(2) . . ?
C11P C12P H12P 119.7 . . ?
C7P C12P H12P 119.7 . . ?
C3T C1T C2T 108.2(2) . . ?
C3T C1T C4P 112.2(2) . . ?
C2T C1T C4P 110.6(2) . . ?
C3T C1T C4T 108.4(2) . . ?
C2T C1T C4T 109.6(2) . . ?
C4P C1T C4T 107.7(2) . . ?
C1T C2T H2TA 109.5 . . ?
C1T C2T H2TB 109.5 . . ?
H2TA C2T H2TB 109.5 . . ?
C1T C2T H2TC 109.5 . . ?
H2TA C2T H2TC 109.5 . . ?
H2TB C2T H2TC 109.5 . . ?
C1T C3T H3TA 109.5 . . ?
C1T C3T H3TB 109.5 . . ?
H3TA C3T H3TB 109.5 . . ?
C1T C3T H3TC 109.5 . . ?
H3TA C3T H3TC 109.5 . . ?
H3TB C3T H3TC 109.5 . . ?
C1T C4T H4TA 109.5 . . ?
C1T C4T H4TB 109.5 . . ?
H4TA C4T H4TB 109.5 . . ?
C1T C4T H4TC 109.5 . . ?
H4TA C4T H4TC 109.5 . . ?
H4TB C4T H4TC 109.5 . . ?
C8T C5T C6T 109.1(2) . . ?
C8T C5T C7T 108.8(2) . . ?
C6T C5T C7T 108.8(2) . . ?
C8T C5T C10P 108.2(2) . . ?
C6T C5T C10P 110.10(19) . . ?
C7T C5T C10P 111.8(2) . . ?
C5T C6T H6TA 109.5 . . ?
C5T C6T H6TB 109.5 . . ?
H6TA C6T H6TB 109.5 . . ?
C5T C6T H6TC 109.5 . . ?
H6TA C6T H6TC 109.5 . . ?
H6TB C6T H6TC 109.5 . . ?
C5T C7T H7TA 109.5 . . ?
C5T C7T H7TB 109.5 . . ?
H7TA C7T H7TB 109.5 . . ?
C5T C7T H7TC 109.5 . . ?
H7TA C7T H7TC 109.5 . . ?
H7TB C7T H7TC 109.5 . . ?
C5T C8T H8TA 109.5 . . ?
C5T C8T H8TB 109.5 . . ?
H8TA C8T H8TB 109.5 . . ?
C5T C8T H8TC 109.5 . . ?
H8TA C8T H8TC 109.5 . . ?
H8TB C8T H8TC 109.5 . . ?
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 O1 1.4850(16) . ?
P1 C7P 1.805(2) . ?
P1 C1P 1.806(2) . ?
P1 C1 1.843(2) . ?
O2 C2 1.236(2) . ?
O2' C2' 1.228(3) . ?
N1 C2 1.350(3) . ?
N1 C3 1.466(3) . ?
N1 C7 1.473(3) . ?
N1' C2' 1.349(3) . ?
N1' C7' 1.470(3) . ?
N1' C3' 1.470(3) . ?
C1 C2 1.518(3) . ?
C1 C1' 1.533(3) . ?
C1 H1 1.0000 . ?
C3 C4 1.525(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C6 1.518(4) . ?
C4 C5 1.527(4) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.522(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.523(3) . ?
C8 C9 1.526(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 0.9800 . ?
C1' C2' 1.506(3) . ?
C1' H2A 0.9900 . ?
C1' H2B 0.9900 . ?
C3' C4' 1.526(3) . ?
C3' H3'A 0.9900 . ?
C3' H3'B 0.9900 . ?
C4' C6' 1.519(4) . ?
C4' C5' 1.525(4) . ?
C4' H4' 1.0000 . ?
C5' H5'A 0.9800 . ?
C5' H5'B 0.9800 . ?
C5' H5'C 0.9800 . ?
C6' H6'A 0.9800 . ?
C6' H6'B 0.9800 . ?
C6' H6'C 0.9800 . ?
C7' C8' 1.534(3) . ?
C7' H7'A 0.9900 . ?
C7' H7'B 0.9900 . ?
C8' C10' 1.521(4) . ?
C8' C9' 1.527(3) . ?
C8' H8' 1.0000 . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
C10' H10A 0.9800 . ?
C10' H10B 0.9800 . ?
C10' H10C 0.9800 . ?
C1P C6P 1.389(3) . ?
C1P C2P 1.397(3) . ?
C2P C3P 1.376(3) . ?
C2P H2P 0.9500 . ?
C3P C4P 1.388(3) . ?
C3P H3P 0.9500 . ?
C4P C5P 1.397(3) . ?
C4P C1T 1.531(3) . ?
C5P C6P 1.381(3) . ?
C5P H5P 0.9500 . ?
C6P H6P 0.9500 . ?
C7P C8P 1.392(3) . ?
C7P C12P 1.396(3) . ?
C8P C9P 1.379(3) . ?
C8P H8P 0.9500 . ?
C9P C10P 1.393(3) . ?
C9P H9P 0.9500 . ?
C10P C11P 1.398(3) . ?
C10P C5T 1.535(3) . ?
C11P C12P 1.385(3) . ?
C11P H11P 0.9500 . ?
C12P H12P 0.9500 . ?
C1T C3T 1.524(4) . ?
C1T C2T 1.526(4) . ?
C1T C4T 1.531(4) . ?
C2T H2TA 0.9800 . ?
C2T H2TB 0.9800 . ?
C2T H2TC 0.9800 . ?
C3T H3TA 0.9800 . ?
C3T H3TB 0.9800 . ?
C3T H3TC 0.9800 . ?
C4T H4TA 0.9800 . ?
C4T H4TB 0.9800 . ?
C4T H4TC 0.9800 . ?
C5T C8T 1.530(4) . ?
C5T C6T 1.533(3) . ?
C5T C7T 1.533(4) . ?
C6T H6TA 0.9800 . ?
C6T H6TB 0.9800 . ?
C6T H6TC 0.9800 . ?
C7T H7TA 0.9800 . ?
C7T H7TB 0.9800 . ?
C7T H7TC 0.9800 . ?
C8T H8TA 0.9800 . ?
C8T H8TB 0.9800 . ?
C8T H8TC 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 C1 C2 -171.50(14) . . . . ?
C7P P1 C1 C2 -50.26(17) . . . . ?
C1P P1 C1 C2 67.09(16) . . . . ?
O1 P1 C1 C1' 67.32(16) . . . . ?
C7P P1 C1 C1' -171.44(14) . . . . ?
C1P P1 C1 C1' -54.09(16) . . . . ?
C3 N1 C2 O2 -0.4(3) . . . . ?
C7 N1 C2 O2 -176.01(19) . . . . ?
C3 N1 C2 C1 -179.69(18) . . . . ?
C7 N1 C2 C1 4.7(3) . . . . ?
C1' C1 C2 O2 61.7(2) . . . . ?
P1 C1 C2 O2 -58.9(2) . . . . ?
C1' C1 C2 N1 -119.0(2) . . . . ?
P1 C1 C2 N1 120.47(18) . . . . ?
C2 N1 C3 C4 -71.8(3) . . . . ?
C7 N1 C3 C4 104.0(2) . . . . ?
N1 C3 C4 C6 -58.2(3) . . . . ?
N1 C3 C4 C5 176.9(2) . . . . ?
C2 N1 C7 C8 -85.0(2) . . . . ?
C3 N1 C7 C8 99.5(2) . . . . ?
N1 C7 C8 C10 -68.4(2) . . . . ?
N1 C7 C8 C9 167.84(19) . . . . ?
C2 C1 C1' C2' 69.3(2) . . . . ?
P1 C1 C1' C2' -168.26(15) . . . . ?
C7' N1' C2' O2' 178.5(2) . . . . ?
C3' N1' C2' O2' 0.7(3) . . . . ?
C7' N1' C2' C1' 0.3(3) . . . . ?
C3' N1' C2' C1' -177.51(19) . . . . ?
C1 C1' C2' O2' 21.1(3) . . . . ?
C1 C1' C2' N1' -160.62(19) . . . . ?
C2' N1' C3' C4' 77.5(3) . . . . ?
C7' N1' C3' C4' -100.4(2) . . . . ?
N1' C3' C4' C6' 54.4(3) . . . . ?
N1' C3' C4' C5' 178.43(19) . . . . ?
C2' N1' C7' C8' 82.7(3) . . . . ?
C3' N1' C7' C8' -99.6(2) . . . . ?
N1' C7' C8' C10' 54.5(3) . . . . ?
N1' C7' C8' C9' 178.19(19) . . . . ?
O1 P1 C1P C6P 122.61(19) . . . . ?
C7P P1 C1P C6P -1.3(2) . . . . ?
C1 P1 C1P C6P -117.61(19) . . . . ?
O1 P1 C1P C2P -50.49(19) . . . . ?
C7P P1 C1P C2P -174.45(16) . . . . ?
C1 P1 C1P C2P 69.29(19) . . . . ?
C6P C1P C2P C3P 0.4(3) . . . . ?
P1 C1P C2P C3P 174.03(17) . . . . ?
C1P C2P C3P C4P -0.9(3) . . . . ?
C2P C3P C4P C5P 0.7(3) . . . . ?
C2P C3P C4P C1T -176.6(2) . . . . ?
C3P C4P C5P C6P -0.1(3) . . . . ?
C1T C4P C5P C6P 177.2(2) . . . . ?
C4P C5P C6P C1P -0.4(4) . . . . ?
C2P C1P C6P C5P 0.2(3) . . . . ?
P1 C1P C6P C5P -172.89(18) . . . . ?
O1 P1 C7P C8P 1.08(19) . . . . ?
C1P P1 C7P C8P 124.18(17) . . . . ?
C1 P1 C7P C8P -117.51(17) . . . . ?
O1 P1 C7P C12P 177.96(17) . . . . ?
C1P P1 C7P C12P -58.9(2) . . . . ?
C1 P1 C7P C12P 59.4(2) . . . . ?
C12P C7P C8P C9P -1.5(3) . . . . ?
P1 C7P C8P C9P 175.57(17) . . . . ?
C7P C8P C9P C10P 0.1(3) . . . . ?
C8P C9P C10P C11P 1.4(3) . . . . ?
C8P C9P C10P C5T -179.8(2) . . . . ?
C9P C10P C11P C12P -1.6(3) . . . . ?
C5T C10P C11P C12P 179.7(2) . . . . ?
C10P C11P C12P C7P 0.3(3) . . . . ?
C8P C7P C12P C11P 1.3(3) . . . . ?
P1 C7P C12P C11P -175.50(16) . . . . ?
C3P C4P C1T C3T -14.4(3) . . . . ?
C5P C4P C1T C3T 168.5(2) . . . . ?
C3P C4P C1T C2T -135.3(2) . . . . ?
C5P C4P C1T C2T 47.6(3) . . . . ?
C3P C4P C1T C4T 104.9(3) . . . . ?
C5P C4P C1T C4T -72.2(3) . . . . ?
C9P C10P C5T C8T -71.8(3) . . . . ?
C11P C10P C5T C8T 106.9(3) . . . . ?
C9P C10P C5T C6T 47.4(3) . . . . ?
C11P C10P C5T C6T -134.0(2) . . . . ?
C9P C10P C5T C7T 168.4(2) . . . . ?
C11P C10P C5T C7T -12.9(3) . . . . ?
