#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/44/1514414.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_1514414
loop_
_publ_author_name
'Nako, Adi E.'
'White, Andrew J. P.'
'Crimmin, Mark R.'
_publ_section_title
;
 A metal--amide dependent, catalytic C--H functionalisation of
 triphenylphosphonium methylide
;
_journal_issue                   2
_journal_name_full               'Chemical Science'
_journal_page_first              691
_journal_paper_doi               10.1039/c2sc21123h
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C50 H70 Ca N2 P2 Si4, 2(C7 H8)'
_chemical_formula_sum            'C64 H86 Ca N2 P2 Si4'
_chemical_formula_weight         1097.73
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 128.948(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.6079(11)
_cell_length_b                   12.39475(17)
_cell_length_c                   22.0579(8)
_cell_measurement_reflns_used    12505
_cell_measurement_temperature    173
_cell_measurement_theta_max      32.6416
_cell_measurement_theta_min      3.0421
_cell_volume                     6508.1(6)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 15.9825
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'OD Xcalibur 3'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            37332
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         32.72
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'tabular needles'
_exptl_crystal_F_000             2360
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         10982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0805P)²+3.1897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1446
_reflns_number_gt                8561
_reflns_number_total             10982
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2sc21123h.txt
_cod_data_source_block           2b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1514414
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ca1 Ca 0.5000 0.29066(3) 0.2500 0.02119(8) Uani 1 2 d S
N1 N 0.48998(5) 0.19682(9) 0.33371(7) 0.0248(2) Uani 1 1 d .
Si2 Si 0.550998(17) 0.13187(3) 0.40329(2) 0.02741(9) Uani 1 1 d .
C3 C 0.60296(7) 0.15272(14) 0.38557(11) 0.0386(3) Uani 1 1 d .
H3A H 0.6376 0.1130 0.4248 0.058 Uiso 1 1 calc R
H3B H 0.6115 0.2298 0.3892 0.058 Uiso 1 1 calc R
H3C H 0.5870 0.1262 0.3335 0.058 Uiso 1 1 calc R
C4 C 0.58819(8) 0.18412(18) 0.50557(10) 0.0469(4) Uani 1 1 d .
H4A H 0.5995 0.1232 0.5410 0.070 Uiso 1 1 calc R
H4B H 0.5628 0.2313 0.5062 0.070 Uiso 1 1 calc R
H4C H 0.6216 0.2250 0.5225 0.070 Uiso 1 1 calc R
C5 C 0.54475(9) -0.01874(14) 0.40692(14) 0.0504(5) Uani 1 1 d .
H5A H 0.5645 -0.0413 0.4610 0.076 Uiso 1 1 calc R
H5B H 0.5615 -0.0546 0.3863 0.076 Uiso 1 1 calc R
H5C H 0.5050 -0.0387 0.3753 0.076 Uiso 1 1 calc R
Si6 Si 0.431900(16) 0.18513(3) 0.32683(2) 0.02593(9) Uani 1 1 d .
C7 C 0.37560(6) 0.28323(13) 0.25461(10) 0.0328(3) Uani 1 1 d .
H7A H 0.3909 0.3567 0.2684 0.049 Uiso 1 1 calc R
H7B H 0.3441 0.2784 0.2555 0.049 Uiso 1 1 calc R
H7C H 0.3625 0.2658 0.2022 0.049 Uiso 1 1 calc R
C8 C 0.44522(8) 0.20936(18) 0.42151(10) 0.0446(4) Uani 1 1 d .
H8A H 0.4640 0.2791 0.4432 0.067 Uiso 1 1 calc R
H8B H 0.4692 0.1518 0.4585 0.067 Uiso 1 1 calc R
H8C H 0.4094 0.2098 0.4121 0.067 Uiso 1 1 calc R
C9 C 0.39607(8) 0.04959(14) 0.29233(13) 0.0457(4) Uani 1 1 d .
H9A H 0.3878 0.0313 0.2428 0.069 Uiso 1 1 calc R
H9B H 0.3610 0.0525 0.2849 0.069 Uiso 1 1 calc R
H9C H 0.4208 -0.0055 0.3313 0.069 Uiso 1 1 calc R
C10 C 0.57269(6) 0.45087(11) 0.32235(8) 0.0280(3) Uani 1 1 d .
H10A H 0.6086 0.4181 0.3405 0.034 Uiso 1 1 calc R
H10B H 0.5617 0.5002 0.2795 0.034 Uiso 1 1 calc R
P11 P 0.592282(14) 0.53661(3) 0.396854(19) 0.02242(8) Uani 1 1 d .
C12 C 0.53331(5) 0.57119(11) 0.39331(7) 0.0239(2) Uani 1 1 d .
C13 C 0.50261(7) 0.48803(12) 0.39380(9) 0.0310(3) Uani 1 1 d .
H13A H 0.5127 0.4149 0.3958 0.037 Uiso 1 1 calc R
C14 C 0.45712(7) 0.51311(14) 0.39129(10) 0.0375(3) Uani 1 1 d .
H14A H 0.4368 0.4568 0.3928 0.045 Uiso 1 1 calc R
C15 C 0.44143(7) 0.61925(15) 0.38661(10) 0.0376(3) Uani 1 1 d .
H15A H 0.4099 0.6356 0.3839 0.045 Uiso 1 1 calc R
C16 C 0.47151(7) 0.70149(13) 0.38582(10) 0.0359(3) Uani 1 1 d .
H16A H 0.4606 0.7744 0.3825 0.043 Uiso 1 1 calc R
C17 C 0.51764(6) 0.67805(12) 0.38980(9) 0.0299(3) Uani 1 1 d .
H17A H 0.5386 0.7350 0.3901 0.036 Uiso 1 1 calc R
C18 C 0.62148(6) 0.66594(11) 0.39963(8) 0.0266(3) Uani 1 1 d .
C19 C 0.59516(9) 0.72038(14) 0.32923(11) 0.0441(4) Uani 1 1 d .
H19A H 0.5637 0.6889 0.2821 0.053 Uiso 1 1 calc R
C20 C 0.61481(11) 0.82049(16) 0.32766(14) 0.0562(5) Uani 1 1 d .
H20A H 0.5964 0.8579 0.2797 0.067 Uiso 1 1 calc R
C21 C 0.66135(9) 0.86567(14) 0.39622(14) 0.0496(5) Uani 1 1 d .
H21A H 0.6756 0.9330 0.3950 0.060 Uiso 1 1 calc R
C22 C 0.68686(9) 0.81348(15) 0.46576(14) 0.0505(5) Uani 1 1 d .
H22A H 0.7181 0.8457 0.5128 0.061 Uiso 1 1 calc R
C23 C 0.66719(7) 0.71337(14) 0.46790(10) 0.0402(4) Uani 1 1 d .
H23A H 0.6852 0.6775 0.5163 0.048 Uiso 1 1 calc R
C24 C 0.64542(6) 0.47557(12) 0.49043(8) 0.0302(3) Uani 1 1 d .
C25 C 0.64626(8) 0.49115(17) 0.55327(10) 0.0429(4) Uani 1 1 d .
H25A H 0.6174 0.5320 0.5471 0.051 Uiso 1 1 calc R
C26 C 0.68960(9) 0.4466(2) 0.62600(11) 0.0585(6) Uani 1 1 d .
H26A H 0.6902 0.4573 0.6691 0.070 Uiso 1 1 calc R
C27 C 0.73129(9) 0.3875(2) 0.63498(13) 0.0635(6) Uani 1 1 d .
H27A H 0.7604 0.3567 0.6843 0.076 Uiso 1 1 calc R
C28 C 0.73132(9) 0.3725(2) 0.57343(14) 0.0664(6) Uani 1 1 d .
H28A H 0.7606 0.3325 0.5804 0.080 Uiso 1 1 calc R
C29 C 0.68820(8) 0.41627(17) 0.50036(12) 0.0492(4) Uani 1 1 d .
H29A H 0.6881 0.4056 0.4576 0.059 Uiso 1 1 calc R
C30 C 0.28838(19) 0.8064(3) 0.2328(2) 0.1051(12) Uani 1 1 d .
H30A H 0.2564 0.8555 0.2094 0.158 Uiso 1 1 calc R
H30B H 0.3144 0.8351 0.2251 0.158 Uiso 1 1 calc R
H30C H 0.3078 0.7995 0.2888 0.158 Uiso 1 1 calc R
C31 C 0.26793(10) 0.69877(19) 0.19532(13) 0.0558(5) Uani 1 1 d .
C32 C 0.21407(9) 0.6648(2) 0.16122(14) 0.0609(6) Uani 1 1 d .
H32A H 0.1891 0.7126 0.1596 0.073 Uiso 1 1 calc R
C33 C 0.19592(11) 0.5644(3) 0.12988(17) 0.0766(8) Uani 1 1 d .
H33A H 0.1588 0.5427 0.1078 0.092 Uiso 1 1 calc R
C34 C 0.23104(14) 0.4932(2) 0.12981(19) 0.0766(7) Uani 1 1 d .
H34A H 0.2183 0.4234 0.1075 0.092 Uiso 1 1 calc R
C35 C 0.28354(12) 0.5257(2) 0.16219(16) 0.0672(7) Uani 1 1 d .
H35A H 0.3080 0.4780 0.1626 0.081 Uiso 1 1 calc R
C36 C 0.30257(8) 0.6273(2) 0.19489(13) 0.0595(6) Uani 1 1 d .
H36A H 0.3398 0.6483 0.2173 0.071 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'
Si Si 0.0817 0.0704 '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'
Ca Ca 0.2262 0.3064 '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 Ca1 N1 120.94(6) 2_655 .
N1 Ca1 C10 111.65(4) 2_655 .
N1 Ca1 C10 111.86(4) . .
N1 Ca1 C10 111.86(4) 2_655 2_655
N1 Ca1 C10 111.65(4) . 2_655
C10 Ca1 C10 82.50(7) . 2_655
Si6 N1 Si2 122.43(7) . .
Si6 N1 Ca1 128.16(6) . .
Si2 N1 Ca1 109.31(6) . .
N1 Si2 C3 109.89(7) . .
N1 Si2 C5 115.13(8) . .
C3 Si2 C5 105.49(9) . .
N1 Si2 C4 114.27(7) . .
C3 Si2 C4 104.33(9) . .
C5 Si2 C4 106.85(10) . .
N1 Si6 C7 111.84(6) . .
N1 Si6 C8 113.82(7) . .
C7 Si6 C8 106.30(8) . .
N1 Si6 C9 115.09(8) . .
C7 Si6 C9 104.09(8) . .
C8 Si6 C9 104.79(9) . .
P11 C10 Ca1 134.26(7) . .
C10 P11 C24 110.88(7) . .
C10 P11 C12 111.51(7) . .
C24 P11 C12 107.83(7) . .
C10 P11 C18 116.51(7) . .
C24 P11 C18 105.11(7) . .
C12 P11 C18 104.40(6) . .
C17 C12 C13 119.41(13) . .
C17 C12 P11 121.78(10) . .
C13 C12 P11 118.81(11) . .
C14 C13 C12 119.63(14) . .
C15 C14 C13 120.48(15) . .
C16 C15 C14 120.02(14) . .
C15 C16 C17 120.27(15) . .
C16 C17 C12 120.17(14) . .
C23 C18 C19 119.12(14) . .
C23 C18 P11 123.35(12) . .
C19 C18 P11 117.51(12) . .
C20 C19 C18 120.28(18) . .
C21 C20 C19 119.86(19) . .
C22 C21 C20 120.17(16) . .
C21 C22 C23 120.30(19) . .
C18 C23 C22 120.23(17) . .
C25 C24 C29 119.49(15) . .
C25 C24 P11 121.54(13) . .
C29 C24 P11 118.88(13) . .
C24 C25 C26 119.99(19) . .
C27 C26 C25 120.0(2) . .
C28 C27 C26 120.55(18) . .
C27 C28 C29 120.1(2) . .
C24 C29 C28 119.9(2) . .
C32 C31 C36 117.3(2) . .
C32 C31 C30 121.3(3) . .
C36 C31 C30 121.4(3) . .
C33 C32 C31 121.5(2) . .
C32 C33 C34 120.8(2) . .
C35 C34 C33 118.4(3) . .
C34 C35 C36 121.3(2) . .
C35 C36 C31 120.8(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ca1 N1 2.3596(11) 2_655
Ca1 N1 2.3596(11) .
Ca1 C10 2.6413(14) .
Ca1 C10 2.6413(14) 2_655
N1 Si6 1.6928(12) .
N1 Si2 1.6994(12) .
Si2 C3 1.8789(16) .
Si2 C5 1.8833(18) .
Si2 C4 1.8910(18) .
Si6 C7 1.8800(16) .
Si6 C8 1.8833(17) .
Si6 C9 1.8854(17) .
C10 P11 1.7178(14) .
P11 C24 1.8049(15) .
P11 C12 1.8086(13) .
P11 C18 1.8175(14) .
C12 C17 1.3940(19) .
C12 C13 1.3995(19) .
C13 C14 1.393(2) .
C14 C15 1.382(2) .
C15 C16 1.381(2) .
C16 C17 1.389(2) .
C18 C23 1.386(2) .
C18 C19 1.394(2) .
C19 C20 1.389(2) .
C20 C21 1.386(3) .
C21 C22 1.369(3) .
C22 C23 1.393(2) .
C24 C25 1.384(2) .
C24 C29 1.394(2) .
C25 C26 1.401(3) .
C26 C27 1.373(4) .
C27 C28 1.371(4) .
C28 C29 1.400(3) .
C30 C31 1.484(4) .
C31 C32 1.379(3) .
C31 C36 1.386(3) .
C32 C33 1.361(4) .
C33 C34 1.391(4) .
C34 C35 1.346(4) .
C35 C36 1.384(4) .
