#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/40/2014015.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2014015
loop_
_publ_author_name
'Pretorius, Marié'
'Williams, D. Bradley G.'
'Roodt, Andreas'
'Muller, Alfred'
_publ_section_title
;
 [2-(Anilinomethyl)phenyl]diphenylphosphine and
 {2-[(N-methylanilino)methyl]phenyl}diphenylphosphine
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o384
_journal_page_last               o386
_journal_paper_doi               10.1107/S0108270104007693
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C25 H22 N P'
_chemical_formula_moiety         'C25 H22 N P'
_chemical_formula_sum            'C25 H22 N P'
_chemical_formula_weight         367.41
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.50(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.174(4)
_cell_length_b                   7.9968(16)
_cell_length_c                   22.519(5)
_cell_measurement_reflns_used    789
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.45
_cell_measurement_theta_min      2.7
_cell_volume                     3980.8(14)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART-NT (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 1999)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Berndt, 2001)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16110
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.186
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.862
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0411P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                2201
_reflns_number_total             4943
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj1003.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        3980.7(14)
_cod_original_sg_symbol_Hall     -C2yc
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2014015
_cod_database_fobs_code          2014015
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
P 0.08620(2) 0.22436(7) 0.10666(2) 0.04918(17) Uani d . 1 . . P
N 0.02530(9) 0.3652(2) -0.08252(7) 0.0615(5) Uani d . 1 . . N
C13 0.09251(8) 0.0868(2) 0.04207(8) 0.0431(5) Uani d . 1 . . C
C01 0.11279(10) 0.0904(2) 0.16913(8) 0.0502(5) Uani d . 1 . . C
C18 0.06864(8) 0.1419(2) -0.01423(8) 0.0434(5) Uani d . 1 . . C
C07 0.15072(8) 0.3650(2) 0.10155(7) 0.0448(5) Uani d . 1 . . C
C08 0.15236(10) 0.5100(2) 0.13583(8) 0.0542(6) Uani d . 1 . . C
H08 0.1209 0.5326 0.1596 0.065 Uiso calc R 1 . . H
C20 0.06838(10) 0.4361(2) -0.11593(8) 0.0488(5) Uani d . 1 . . C
C16 0.09611(10) -0.1229(3) -0.05682(10) 0.0613(6) Uani d . 1 . . C
H16 0.0971 -0.1924 -0.0898 0.074 Uiso calc R 1 . . H
C09 0.20008(11) 0.6209(3) 0.13514(9) 0.0629(6) Uani d . 1 . . C
H09 0.2006 0.7165 0.1587 0.075 Uiso calc R 1 . . H
C19 0.04011(9) 0.3135(3) -0.02142(8) 0.0559(6) Uani d . 1 . . C
H19A 0.0034 0.3148 -0.0007 0.067 Uiso calc R 1 . . H
H19B 0.0676 0.3949 -0.0023 0.067 Uiso calc R 1 . . H
C06 0.17079(10) 0.0911(2) 0.19630(9) 0.0574(6) Uani d . 1 . . C
H06 0.2 0.1596 0.1814 0.069 Uiso calc R 1 . . H
C12 0.19853(9) 0.3374(3) 0.06684(9) 0.0593(6) Uani d . 1 . . C
H12 0.1987 0.2413 0.0436 0.071 Uiso calc R 1 . . H
C21 0.12973(9) 0.4280(2) -0.09905(9) 0.0538(5) Uani d . 1 . . C
H21 0.143 0.3732 -0.064 0.065 Uiso calc R 1 . . H
C17 0.07146(9) 0.0358(3) -0.06269(8) 0.0547(5) Uani d . 1 . . C
H17 0.0564 0.0724 -0.1002 0.066 Uiso calc R 1 . . H
C14 0.11712(9) -0.0722(2) 0.04693(9) 0.0553(5) Uani d . 1 . . C
H14 0.1327 -0.1098 0.0841 0.066 Uiso calc R 1 . . H
C10 0.24634(11) 0.5913(3) 0.10028(10) 0.0690(6) Uani d . 1 . . C
H10 0.2782 0.6669 0.0996 0.083 Uiso calc R 1 . . H
C15 0.11921(9) -0.1765(3) -0.00157(10) 0.0628(6) Uani d . 1 . . C
H15 0.1361 -0.2826 0.003 0.075 Uiso calc R 1 . . H
C25 0.04999(11) 0.5184(3) -0.16886(9) 0.0620(6) Uani d . 1 . . C
H25 0.0091 0.5247 -0.1814 0.074 Uiso calc R 1 . . H
C11 0.24577(10) 0.4487(3) 0.06592(10) 0.0740(7) Uani d . 1 . . C
H11 0.2773 0.4277 0.0421 0.089 Uiso calc R 1 . . H
C05 0.18624(12) -0.0091(3) 0.24556(10) 0.0759(7) Uani d . 1 . . C
H05 0.2255 -0.0069 0.2634 0.091 Uiso calc R 1 . . H
C23 0.15288(14) 0.5818(3) -0.18525(11) 0.0779(7) Uani d . 1 . . C
H23 0.1811 0.6307 -0.2083 0.093 Uiso calc R 1 . . H
C24 0.09213(14) 0.5902(3) -0.20248(10) 0.0757(7) Uani d . 1 . . C
H24 0.0793 0.6454 -0.2376 0.091 Uiso calc R 1 . . H
C22 0.17122(11) 0.4998(3) -0.13332(11) 0.0687(6) Uani d . 1 . . C
H22 0.2122 0.4928 -0.1213 0.082 Uiso calc R 1 . . H
C02 0.07125(12) -0.0126(3) 0.19318(10) 0.0816(8) Uani d . 1 . . C
H02 0.0316 -0.0142 0.1763 0.098 Uiso calc R 1 . . H
C04 0.14409(16) -0.1106(3) 0.26785(11) 0.0905(9) Uani d . 1 . . C
H04 0.1545 -0.1775 0.3008 0.109 Uiso calc R 1 . . H
C03 0.08701(14) -0.1132(4) 0.24164(12) 0.0991(9) Uani d . 1 . . C
H03 0.0583 -0.1834 0.2564 0.119 Uiso calc R 1 . . H
H1 -0.0112(10) 0.402(3) -0.0913(9) 0.074(8) Uiso d . 1 . . H
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 0 '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'
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_publ_flag
C01 P C07 101.66(9) y
C01 P C13 102.61(9) y
C07 P C13 102.09(8) y
C20 N C19 121.23(18) y
C20 N H1 114.1(14) ?
C19 N H1 116.8(14) ?
C14 C13 C18 118.50(17) ?
C14 C13 P 122.75(14) ?
C18 C13 P 118.67(14) ?
C02 C01 C06 117.17(19) ?
C02 C01 P 117.87(17) ?
C06 C01 P 124.85(16) ?
C17 C18 C13 118.75(18) ?
C17 C18 C19 120.93(17) ?
C13 C18 C19 120.32(16) ?
C12 C07 C08 117.28(18) ?
C12 C07 P 125.10(15) ?
C08 C07 P 117.61(15) ?
C09 C08 C07 121.01(19) ?
C09 C08 H08 119.5 ?
C07 C08 H08 119.5 ?
N C20 C21 122.49(18) ?
N C20 C25 119.36(19) ?
C21 C20 C25 118.15(19) ?
C15 C16 C17 119.23(18) ?
C15 C16 H16 120.4 ?
C17 C16 H16 120.4 ?
C10 C09 C08 120.5(2) ?
C10 C09 H09 119.7 ?
C08 C09 H09 119.7 ?
N C19 C18 114.94(16) ?
N C19 H19A 108.5 ?
C18 C19 H19A 108.5 ?
N C19 H19B 108.5 ?
C18 C19 H19B 108.5 ?
H19A C19 H19B 107.5 ?
C01 C06 C05 121.0(2) ?
C01 C06 H06 119.5 ?
C05 C06 H06 119.5 ?
C11 C12 C07 121.56(19) ?
C11 C12 H12 119.2 ?
C07 C12 H12 119.2 ?
C22 C21 C20 120.9(2) ?
C22 C21 H21 119.5 ?
C20 C21 H21 119.5 ?
C16 C17 C18 121.81(18) ?
C16 C17 H17 119.1 ?
C18 C17 H17 119.1 ?
C15 C14 C13 122.05(19) ?
C15 C14 H14 119 ?
C13 C14 H14 119 ?
C09 C10 C11 119.6(2) ?
C09 C10 H10 120.2 ?
C11 C10 H10 120.2 ?
C16 C15 C14 119.6(2) ?
C16 C15 H15 120.2 ?
C14 C15 H15 120.2 ?
C24 C25 C20 120.2(2) ?
C24 C25 H25 119.9 ?
C20 C25 H25 119.9 ?
C12 C11 C10 120.0(2) ?
C12 C11 H11 120 ?
C10 C11 H11 120 ?
C04 C05 C06 120.3(2) ?
C04 C05 H05 119.9 ?
C06 C05 H05 119.9 ?
C24 C23 C22 118.8(2) ?
C24 C23 H23 120.6 ?
C22 C23 H23 120.6 ?
C25 C24 C23 121.2(2) ?
C25 C24 H24 119.4 ?
C23 C24 H24 119.4 ?
C21 C22 C23 120.8(2) ?
C21 C22 H22 119.6 ?
C23 C22 H22 119.6 ?
C01 C02 C03 121.6(2) ?
C01 C02 H02 119.2 ?
C03 C02 H02 119.2 ?
C03 C04 C05 119.6(2) ?
C03 C04 H04 120.2 ?
C05 C04 H04 120.2 ?
C04 C03 C02 120.4(3) ?
C04 C03 H03 119.8 ?
C02 C03 H03 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P C01 . 1.829(2) y
P C07 . 1.830(2) y
P C13 . 1.8378(19) y
N C20 . 1.383(2) y
N C19 . 1.450(2) y
N H1 . 0.87(2) ?
C13 C14 . 1.385(3) ?
C13 C18 . 1.406(2) ?
C01 C02 . 1.378(3) ?
C01 C06 . 1.380(3) ?
C18 C17 . 1.387(2) ?
C18 C19 . 1.514(3) ?
C07 C12 . 1.383(3) ?
C07 C08 . 1.392(2) ?
C08 C09 . 1.382(3) ?
C08 H08 . 0.93 ?
C20 C21 . 1.385(3) ?
C20 C25 . 1.394(3) ?
C16 C15 . 1.376(3) ?
C16 C17 . 1.384(3) ?
C16 H16 . 0.93 ?
C09 C10 . 1.361(3) ?
C09 H09 . 0.93 ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C06 C05 . 1.389(3) ?
C06 H06 . 0.93 ?
C12 C11 . 1.376(3) ?
C12 H12 . 0.93 ?
C21 C22 . 1.372(3) ?
C21 H21 . 0.93 ?
C17 H17 . 0.93 ?
C14 C15 . 1.378(3) ?
C14 H14 . 0.93 ?
C10 C11 . 1.377(3) ?
C10 H10 . 0.93 ?
C15 H15 . 0.93 ?
C25 C24 . 1.374(3) ?
C25 H25 . 0.93 ?
C11 H11 . 0.93 ?
C05 C04 . 1.363(3) ?
C05 H05 . 0.93 ?
C23 C24 . 1.374(3) ?
C23 C22 . 1.374(3) ?
C23 H23 . 0.93 ?
C24 H24 . 0.93 ?
C22 H22 . 0.93 ?
C02 C03 . 1.379(3) ?
C02 H02 . 0.93 ?
C04 C03 . 1.354(4) ?
C04 H04 . 0.93 ?
C03 H03 . 0.93 ?
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_publ_flag
C01 P C13 C14 -4.49(18) ?
C07 P C13 C14 100.56(17) ?
C01 P C13 C18 172.24(15) ?
C07 P C13 C18 -82.71(15) ?
C07 P C01 C02 168.20(17) ?
C13 P C01 C02 -86.41(18) ?
C07 P C01 C06 -8.05(19) ?
C13 P C01 C06 97.34(18) ?
C14 C13 C18 C17 -0.9(3) ?
P C13 C18 C17 -177.77(14) ?
C14 C13 C18 C19 178.73(17) ?
P C13 C18 C19 1.9(2) ?
C01 P C07 C12 90.71(17) ?
C13 P C07 C12 -15.08(18) ?
C01 P C07 C08 -88.35(15) ?
C13 P C07 C08 165.86(14) ?
C12 C07 C08 C09 -0.2(3) ?
P C07 C08 C09 178.89(15) ?
C19 N C20 C21 15.0(3) ?
C19 N C20 C25 -165.43(18) ?
C07 C08 C09 C10 0.7(3) ?
C20 N C19 C18 -83.4(2) y
C17 C18 C19 N -9.0(3) ?
C13 C18 C19 N 171.35(17) ?
C02 C01 C06 C05 0.4(3) ?
P C01 C06 C05 176.66(15) ?
C08 C07 C12 C11 -0.2(3) ?
P C07 C12 C11 -179.30(16) ?
N C20 C21 C22 179.95(19) ?
C25 C20 C21 C22 0.3(3) ?
C15 C16 C17 C18 -0.9(3) ?
C13 C18 C17 C16 1.1(3) ?
C19 C18 C17 C16 -178.52(18) ?
C18 C13 C14 C15 0.5(3) ?
P C13 C14 C15 177.21(15) ?
C08 C09 C10 C11 -0.7(3) ?
C17 C16 C15 C14 0.4(3) ?
C13 C14 C15 C16 -0.2(3) ?
N C20 C25 C24 179.75(19) ?
C21 C20 C25 C24 -0.6(3) ?
C07 C12 C11 C10 0.3(3) ?
C09 C10 C11 C12 0.2(3) ?
C01 C06 C05 C04 0.2(3) ?
C20 C25 C24 C23 0.5(3) ?
C22 C23 C24 C25 0.0(4) ?
C20 C21 C22 C23 0.1(3) ?
C24 C23 C22 C21 -0.3(3) ?
C06 C01 C02 C03 -1.2(3) ?
P C01 C02 C03 -177.7(2) ?
C06 C05 C04 C03 0.0(4) ?
C05 C04 C03 C02 -0.8(4) ?
C01 C02 C03 C04 1.4(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21134218
