#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:20:56 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178560 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/68/4066892.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_4066892
loop_
_publ_author_name
'Ionkin, Alex S.'
'Marshall, William J.'
'Fish, Brian M.'
'Howe, Laurie A.'
_publ_section_title
;
 Fragmentation of an N-Substituted One-Coordinate Phosphorus
 (Phosphaalkyne): Plausible Generation of Monovalent Phosphorus
 Species†
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              4154
_journal_paper_doi               10.1021/om100691g
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C19 H28 N'
_chemical_formula_weight         270.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           63
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2c 2'
_symmetry_space_group_name_H-M   'C m c m'
_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                   16.888(10)
_cell_length_b                   11.023(7)
_cell_length_c                   9.623(6)
_cell_measurement_reflns_used    515
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.69
_cell_measurement_theta_min      2.20
_cell_volume                     1791.4(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0619
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2946
_diffrn_reflns_theta_full        25.23
_diffrn_reflns_theta_max         25.23
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.003
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irre.plate
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0717
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.1993
_reflns_number_gt                470
_reflns_number_total             884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100691g_si_001.cif
_cod_data_source_block           08135
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1791.3(18)
_cod_original_sg_symbol_H-M      Cmcm
_cod_database_code               4066892
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'x+1/2, -y+1/2, z-1/2'
'-x+1/2, y+1/2, 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
C1 C 0.0000 0.2208(4) 0.2500 0.0593(17) Uani 1 4 d S
C2 C 0.0738(3) 0.2811(3) 0.2500 0.0541(11) Uani 1 2 d S
C3 C 0.0701(2) 0.4065(3) 0.2500 0.0446(10) Uani 1 2 d S
H3A H 0.1174 0.4495 0.2500 0.054 Uiso 1 2 calc SR
C4 C 0.0000 0.4715(4) 0.2500 0.0334(11) Uani 1 4 d S
N1 N 0.0000 0.0932(5) 0.2500 0.088(2) Uani 1 4 d S
C6 C 0.0000 -0.0121(7) 0.2500 0.139(4) Uani 1 4 d S
C7 C 0.1565(3) 0.2176(4) 0.2500 0.0826(17) Uani 1 2 d S
C8 C 0.1646(2) 0.1382(3) 0.1194(4) 0.1005(15) Uani 1 1 d .
H8A H 0.2152 0.0983 0.1202 0.151 Uiso 1 1 calc R
H8B H 0.1605 0.1882 0.0380 0.151 Uiso 1 1 calc R
H8C H 0.1233 0.0784 0.1185 0.151 Uiso 1 1 calc R
C9 C 0.2247(4) 0.3124(6) 0.2500 0.111(2) Uani 1 2 d S
H9A H 0.271(5) 0.267(7) 0.2500 0.166 Uiso 1 2 d S
H9B H 0.217(6) 0.359(9) 0.140(12) 0.166 Uiso 0.50 1 d P
C10 C 0.0000 0.6102(4) 0.2500 0.0356(12) Uani 1 4 d S
C11 C -0.0453(4) 0.6554(5) 0.1200(6) 0.0528(14) Uani 0.50 1 d P
C12 C -0.0817(5) 0.6627(8) 0.2500 0.055(2) Uani 0.50 2 d SP
H11' H 0.0000 0.628(4) 0.040(6) 0.095(15) Uiso 1 2 d S
H12 H -0.072(4) 0.769(7) 0.2500 0.18(3) Uiso 1 2 d S
H12' H -0.109(2) 0.627(3) 0.145(4) 0.097(11) Uiso 1 1 d .
H11 H -0.044(2) 0.750(5) 0.121(5) 0.049(13) Uiso 0.50 1 d P
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'
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 C1 C2 118.1(2) . .
N1 C1 C2 118.1(2) . 3
C2 C1 C2 123.8(4) . 3
C3 C2 C1 115.5(4) . .
C3 C2 C7 119.2(4) . .
C1 C2 C7 125.3(4) . .
C2 C3 C4 123.8(4) . .
C3 C4 C3 117.6(4) . 3
C3 C4 C10 121.2(2) . .
C3 C4 C10 121.2(2) 3 .
C6 N1 C1 180.000(1) . .
C8 C7 C8 109.6(4) . 10_556
C8 C7 C9 108.4(3) . .
C8 C7 C9 108.4(3) 10_556 .
C8 C7 C2 109.6(3) . .
C8 C7 C2 109.6(3) 10_556 .
C9 C7 C2 111.2(4) . .
C12 C10 C12 134.5(7) 3 .
C12 C10 C4 112.7(4) 3 .
C12 C10 C4 112.7(4) . .
C12 C10 C11 54.6(3) 3 3
C12 C10 C11 109.3(3) . 3
C4 C10 C11 108.8(3) . 3
C12 C10 C11 109.3(3) 3 10_556
C12 C10 C11 54.6(3) . 10_556
C4 C10 C11 108.8(3) . 10_556
C11 C10 C11 59.2(5) 3 10_556
C12 C10 C11 54.6(3) 3 12
C12 C10 C11 109.3(3) . 12
C4 C10 C11 108.8(3) . 12
C11 C10 C11 107.8(5) 3 12
C11 C10 C11 142.5(5) 10_556 12
C12 C10 C11 109.3(3) 3 .
C12 C10 C11 54.6(3) . .
C4 C10 C11 108.8(3) . .
C11 C10 C11 142.5(5) 3 .
C11 C10 C11 107.8(5) 10_556 .
C11 C10 C11 59.2(5) 12 .
C12 C11 C11 116.2(4) . 12
C12 C11 C10 60.8(4) . .
C11 C11 C10 60.4(2) 12 .
C11 C12 C11 127.2(8) 10_556 .
C11 C12 C10 64.6(4) 10_556 .
C11 C12 C10 64.6(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.406(7) .
C1 C2 1.413(5) .
C1 C2 1.413(5) 3
C2 C3 1.383(5) .
C2 C7 1.562(6) .
C3 C4 1.384(4) .
C4 C3 1.384(4) 3
C4 C10 1.529(6) .
N1 C6 1.161(9) .
C7 C8 1.538(4) .
C7 C8 1.538(4) 10_556
C7 C9 1.555(8) .
C10 C12 1.497(8) 3
C10 C12 1.497(8) .
C10 C11 1.548(5) 3
C10 C11 1.548(5) 10_556
C10 C11 1.548(5) 12
C10 C11 1.548(5) .
C11 C12 1.397(7) .
C11 C11 1.529(13) 12
C12 C11 1.397(7) 10_556
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_4
N1 C1 C2 C3 180.0 . .
C2 C1 C2 C3 0.0 3 .
N1 C1 C2 C7 0.0 . .
C2 C1 C2 C7 180.0 3 .
C1 C2 C3 C4 0.0 . .
C7 C2 C3 C4 180.0 . .
C2 C3 C4 C3 0.0 . 3
C2 C3 C4 C10 180.0 . .
C2 C1 N1 C6 0(100) . .
C2 C1 N1 C6 0(100) 3 .
C3 C2 C7 C8 -119.8(3) . .
C1 C2 C7 C8 60.2(3) . .
C3 C2 C7 C8 119.8(3) . 10_556
C1 C2 C7 C8 -60.2(3) . 10_556
C3 C2 C7 C9 0.0 . .
C1 C2 C7 C9 180.0 . .
C3 C4 C10 C12 0.0 . 3
C3 C4 C10 C12 180.0 3 3
C3 C4 C10 C12 180.0 . .
C3 C4 C10 C12 0.0 3 .
C3 C4 C10 C11 -58.6(3) . 3
C3 C4 C10 C11 121.4(3) 3 3
C3 C4 C10 C11 -121.4(3) . 10_556
C3 C4 C10 C11 58.6(3) 3 10_556
C3 C4 C10 C11 58.6(3) . 12
C3 C4 C10 C11 -121.4(3) 3 12
C3 C4 C10 C11 121.4(3) . .
C3 C4 C10 C11 -58.6(3) 3 .
C12 C10 C11 C12 -131.5(8) 3 .
C4 C10 C11 C12 105.0(4) . .
C11 C10 C11 C12 -75.0(4) 3 .
C11 C10 C11 C12 -12.7(6) 10_556 .
C11 C10 C11 C12 -153.8(4) 12 .
C12 C10 C11 C11 22.4(3) 3 12
C12 C10 C11 C11 153.8(4) . 12
C4 C10 C11 C11 -101.12(18) . 12
C11 C10 C11 C11 78.88(18) 3 12
C11 C10 C11 C11 141.1(5) 10_556 12
C11 C11 C12 C11 -8.3(11) 12 10_556
C10 C11 C12 C11 17.0(8) . 10_556
C11 C11 C12 C10 -25.3(4) 12 .
C12 C10 C12 C11 -82.5(4) 3 10_556
C4 C10 C12 C11 97.5(4) . 10_556
C11 C10 C12 C11 -23.6(4) 3 10_556
C11 C10 C12 C11 -141.4(5) 12 10_556
C11 C10 C12 C11 -165.1(7) . 10_556
C12 C10 C12 C11 82.5(4) 3 .
C4 C10 C12 C11 -97.5(4) . .
C11 C10 C12 C11 141.4(5) 3 .
C11 C10 C12 C11 165.1(7) 10_556 .
C11 C10 C12 C11 23.6(4) 12 .
