#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:49:47 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179492 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/89/4338984.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_4338984
loop_
_publ_author_name
'Thirupathi, Natesan'
'Stricklen, Phillip M.'
'Liu, Xiaodong'
'Oshel, Reed'
'Guzei, Ilia'
'Ellern, Arkady'
'Verkade, John G.'
_publ_section_title
;
 Comparisons of phosphorus ligation properties in P(CH2NR)3P.
;
_journal_issue                   22
_journal_name_full               'Inorganic chemistry'
_journal_page_first              9351
_journal_page_last               9363
_journal_paper_doi               10.1021/ic0703070
_journal_volume                  46
_journal_year                    2007
_chemical_formula_sum            'C21 H21 N3 P2'
_chemical_formula_weight         377.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.5599(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2430(4)
_cell_length_b                   18.6675(8)
_cell_length_c                   10.5701(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1904.49(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3885
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.9539
_exptl_absorpt_correction_T_min  0.8902
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0326
_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)+(0.0721P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                3218
_reflns_number_total             3885
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0703070-file003.cif
_cod_data_source_block           ver44
_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/ACS/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      P2(1)/n
_cod_database_code               4338984
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
P1 P 0.94835(4) 0.18181(2) 0.83636(4) 0.02377(13) Uani 1 1 d .
P2 P 0.67888(4) 0.10323(2) 0.65985(4) 0.02937(13) Uani 1 1 d .
N1 N 0.96571(13) 0.10288(6) 0.76202(13) 0.0272(3) Uani 1 1 d .
N2 N 0.83253(12) 0.15408(7) 0.91055(12) 0.0286(3) Uani 1 1 d .
N3 N 0.83734(12) 0.22649(7) 0.70145(12) 0.0281(3) Uani 1 1 d .
C1 C 0.84558(15) 0.05374(9) 0.71575(16) 0.0324(4) Uani 1 1 d .
H1A H 0.8472 0.0216 0.7884 0.039 Uiso 1 1 calc R
H1B H 0.8528 0.0250 0.6420 0.039 Uiso 1 1 calc R
C2 C 1.07820(14) 0.09161(8) 0.71545(14) 0.0255(3) Uani 1 1 d .
C3 C 1.15076(15) 0.14942(8) 0.68750(15) 0.0286(3) Uani 1 1 d .
H3 H 1.1244 0.1960 0.6988 0.034 Uiso 1 1 calc R
C4 C 1.26208(16) 0.13775(9) 0.64291(16) 0.0337(4) Uani 1 1 d .
H4 H 1.3111 0.1766 0.6266 0.040 Uiso 1 1 calc R
C5 C 1.30066(17) 0.06874(9) 0.62249(17) 0.0385(4) Uani 1 1 d .
H5 H 1.3740 0.0610 0.5909 0.046 Uiso 1 1 calc R
C6 C 1.22873(18) 0.01158(9) 0.64969(17) 0.0384(4) Uani 1 1 d .
H6 H 1.2542 -0.0349 0.6361 0.046 Uiso 1 1 calc R
C7 C 1.11916(16) 0.02221(9) 0.69687(15) 0.0330(4) Uani 1 1 d .
H7 H 1.0729 -0.0169 0.7161 0.040 Uiso 1 1 calc R
C8 C 0.68880(15) 0.13921(9) 0.82614(15) 0.0308(3) Uani 1 1 d .
H8A H 0.6351 0.1830 0.8138 0.037 Uiso 1 1 calc R
H8B H 0.6486 0.1049 0.8713 0.037 Uiso 1 1 calc R
C9 C 0.86579(15) 0.15896(8) 1.05124(14) 0.0252(3) Uani 1 1 d .
C10 C 1.00446(16) 0.15524(8) 1.13537(15) 0.0302(3) Uani 1 1 d .
H10 H 1.0742 0.1478 1.0987 0.036 Uiso 1 1 calc R
C11 C 1.03787(18) 0.16261(9) 1.27317(16) 0.0354(4) Uani 1 1 d .
H11 H 1.1303 0.1617 1.3279 0.042 Uiso 1 1 calc R
C12 C 0.93553(18) 0.17123(9) 1.33012(17) 0.0369(4) Uani 1 1 d .
H12 H 0.9586 0.1760 1.4226 0.044 Uiso 1 1 calc R
C13 C 0.79846(18) 0.17266(8) 1.24782(17) 0.0345(4) Uani 1 1 d .
H13 H 0.7291 0.1776 1.2858 0.041 Uiso 1 1 calc R
C14 C 0.76272(17) 0.16691(8) 1.10973(16) 0.0301(3) Uani 1 1 d .
H14 H 0.6700 0.1683 1.0558 0.036 Uiso 1 1 calc R
C15 C 0.73893(16) 0.18421(8) 0.59395(15) 0.0309(4) Uani 1 1 d .
H15A H 0.7830 0.1699 0.5298 0.037 Uiso 1 1 calc R
H15B H 0.6596 0.2138 0.5472 0.037 Uiso 1 1 calc R
C16 C 0.86531(14) 0.29827(8) 0.67646(15) 0.0256(3) Uani 1 1 d .
C17 C 0.84559(15) 0.32347(9) 0.54705(16) 0.0312(4) Uani 1 1 d .
H17 H 0.8121 0.2927 0.4741 0.037 Uiso 1 1 calc R
C18 C 0.87568(17) 0.39407(9) 0.52652(18) 0.0382(4) Uani 1 1 d .
H18 H 0.8610 0.4106 0.4398 0.046 Uiso 1 1 calc R
C19 C 0.92757(18) 0.44011(9) 0.63479(19) 0.0422(4) Uani 1 1 d .
H19 H 0.9502 0.4871 0.6211 0.051 Uiso 1 1 calc R
C20 C 0.94554(18) 0.41591(9) 0.76294(19) 0.0389(4) Uani 1 1 d .
H20 H 0.9796 0.4469 0.8355 0.047 Uiso 1 1 calc R
C21 C 0.91335(15) 0.34608(8) 0.78424(16) 0.0302(4) Uani 1 1 d .
H21 H 0.9236 0.3307 0.8707 0.036 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'
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
N2 P1 N1 98.36(6)
N2 P1 N3 99.22(6)
N1 P1 N3 100.33(6)
C8 P2 C15 98.11(7)
C8 P2 C1 97.25(7)
C15 P2 C1 98.05(7)
C2 N1 C1 118.52(12)
C2 N1 P1 120.80(10)
C1 N1 P1 118.93(10)
C9 N2 C8 119.38(12)
C9 N2 P1 120.28(10)
C8 N2 P1 119.16(10)
C16 N3 C15 119.58(12)
C16 N3 P1 119.83(9)
C15 N3 P1 118.29(10)
N1 C1 P2 111.78(11)
C7 C2 C3 118.75(13)
C7 C2 N1 120.41(13)
C3 C2 N1 120.85(13)
C4 C3 C2 120.40(14)
C5 C4 C3 120.53(15)
C6 C5 C4 119.10(15)
C5 C6 C7 121.12(15)
C6 C7 C2 120.08(15)
N2 C8 P2 111.72(10)
C14 C9 C10 118.63(14)
C14 C9 N2 121.36(13)
C10 C9 N2 120.01(13)
C11 C10 C9 120.15(15)
C12 C11 C10 120.83(16)
C11 C12 C13 119.14(15)
C12 C13 C14 121.07(15)
C13 C14 C9 120.12(15)
N3 C15 P2 112.03(10)
C17 C16 C21 118.60(14)
C17 C16 N3 122.05(13)
C21 C16 N3 119.35(13)
C18 C17 C16 120.44(15)
C17 C18 C19 120.23(16)
C20 C19 C18 119.69(16)
C19 C20 C21 120.53(16)
C20 C21 C16 120.45(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 N2 1.7067(12)
P1 N1 1.7069(13)
P1 N3 1.7136(13)
P2 C8 1.8524(16)
P2 C15 1.8536(15)
P2 C1 1.8554(16)
N1 C2 1.4121(18)
N1 C1 1.4806(19)
N2 C9 1.4131(19)
N2 C8 1.4700(19)
N3 C16 1.414(2)
N3 C15 1.4708(18)
C2 C7 1.396(2)
C2 C3 1.397(2)
C3 C4 1.389(2)
C4 C5 1.385(2)
C5 C6 1.381(2)
C6 C7 1.387(2)
C9 C14 1.399(2)
C9 C10 1.403(2)
C10 C11 1.387(2)
C11 C12 1.382(2)
C12 C13 1.382(2)
C13 C14 1.385(2)
C16 C17 1.396(2)
C16 C21 1.400(2)
C17 C18 1.387(2)
C18 C19 1.387(3)
C19 C20 1.381(2)
C20 C21 1.381(2)
