#------------------------------------------------------------------------------
#$Date: 2016-03-25 15:56:59 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179944 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/39/7023977.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_7023977
loop_
_publ_author_name
'Kreye, Markus'
'Runyon, Jason W.'
'Freytag, Matthias'
'Jones, Peter G.'
'Walter, Marc D.'
_publ_section_title
;
 Phosphine-substituted sterically encumbered pyrrolyl ligands - synthesis
 and reactivity studies.
;
_journal_issue                   48
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              16846
_journal_page_last               16856
_journal_paper_doi               10.1039/c3dt52205a
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C16 H28 Cl2 N O P'
_chemical_formula_weight         352.26
_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                 98.371(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1434(3)
_cell_length_b                   15.4257(4)
_cell_length_c                   12.2878(3)
_cell_measurement_reflns_used    12586
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2064
_cell_measurement_theta_min      2.4163
_cell_volume                     1902.18(9)
_computing_cell_refinement
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) 
(compiled Oct 27 2011,15:02:11) 
;
_computing_data_collection
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) 
(compiled Oct 27 2011,15:02:11) 
;
_computing_data_reduction
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) 
(compiled Oct 27 2011,15:02:11) 
;
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            56111
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) 
(compiled Oct 27 2011,15:02:11) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0328
_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)+(0.0231P)²+1.0357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0693
_reflns_number_gt                3597
_reflns_number_total             4318
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt52205a.txt
_cod_data_source_block           jason01
_cod_original_cell_volume        1902.17(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7023977
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
N N 0.59918(11) 0.63702(7) 0.62760(9) 0.0116(2) Uani 1 1 d .
H1 H 0.5378(16) 0.6716(11) 0.6016(13) 0.019(4) Uiso 1 1 d .
P P 0.97410(4) 0.55819(2) 0.68597(3) 0.01755(9) Uani 1 1 d .
Cl1 Cl 1.01523(4) 0.53598(3) 0.85557(3) 0.02836(10) Uani 1 1 d .
Cl2 Cl 0.97099(4) 0.42877(2) 0.63616(3) 0.02746(10) Uani 1 1 d .
C1 C 0.73133(13) 0.65038(9) 0.62054(10) 0.0119(3) Uani 1 1 d .
C2 C 0.79980(13) 0.57927(9) 0.67159(11) 0.0135(3) Uani 1 1 d .
C3 C 0.70248(13) 0.52365(9) 0.70981(11) 0.0139(3) Uani 1 1 d .
H3 H 0.7204 0.4704 0.7480 0.017 Uiso 1 1 calc R
C4 C 0.58033(13) 0.56033(9) 0.68196(10) 0.0121(3) Uani 1 1 d .
C5 C 0.77128(13) 0.73145(9) 0.56310(11) 0.0148(3) Uani 1 1 d .
C6 C 0.92254(14) 0.74427(10) 0.57944(13) 0.0216(3) Uani 1 1 d .
H6A H 0.9562 0.7469 0.6583 0.032 Uiso 1 1 calc R
H6B H 0.9438 0.7985 0.5442 0.032 Uiso 1 1 calc R
H6C H 0.9644 0.6956 0.5463 0.032 Uiso 1 1 calc R
C7 C 0.70780(15) 0.81188(9) 0.60903(12) 0.0204(3) Uani 1 1 d .
H7A H 0.7364 0.8156 0.6886 0.031 Uiso 1 1 calc R
H7B H 0.6105 0.8070 0.5942 0.031 Uiso 1 1 calc R
H7C H 0.7362 0.8642 0.5735 0.031 Uiso 1 1 calc R
C8 C 0.72157(16) 0.72397(10) 0.43872(12) 0.0213(3) Uani 1 1 d .
H8A H 0.7427 0.7775 0.4018 0.032 Uiso 1 1 calc R
H8B H 0.6249 0.7149 0.4269 0.032 Uiso 1 1 calc R
H8C H 0.7655 0.6748 0.4084 0.032 Uiso 1 1 calc R
C9 C 0.44346(13) 0.53201(9) 0.70310(11) 0.0136(3) Uani 1 1 d .
C10 C 0.38647(14) 0.59837(10) 0.77718(12) 0.0206(3) Uani 1 1 d .
H10A H 0.4451 0.6023 0.8478 0.031 Uiso 1 1 calc R
H10B H 0.2974 0.5799 0.7896 0.031 Uiso 1 1 calc R
H10C H 0.3806 0.6553 0.7413 0.031 Uiso 1 1 calc R
C11 C 0.34848(14) 0.52385(10) 0.59385(11) 0.0180(3) Uani 1 1 d .
H11A H 0.3377 0.5807 0.5580 0.027 Uiso 1 1 calc R
H11B H 0.2615 0.5029 0.6084 0.027 Uiso 1 1 calc R
H11C H 0.3857 0.4828 0.5456 0.027 Uiso 1 1 calc R
C12 C 0.45501(15) 0.44386(10) 0.76115(12) 0.0209(3) Uani 1 1 d .
H12A H 0.4921 0.4013 0.7147 0.031 Uiso 1 1 calc R
H12B H 0.3665 0.4248 0.7743 0.031 Uiso 1 1 calc R
H12C H 0.5138 0.4491 0.8316 0.031 Uiso 1 1 calc R
O O 0.37993(10) 0.74649(7) 0.53889(8) 0.0221(2) Uani 1 1 d .
C96 C 0.30464(15) 0.80954(10) 0.59149(12) 0.0234(3) Uani 1 1 d .
H96A H 0.3650 0.8470 0.6417 0.028 Uiso 1 1 calc R
H96B H 0.2420 0.7803 0.6342 0.028 Uiso 1 1 calc R
C97 C 0.22921(15) 0.86261(10) 0.49864(12) 0.0207(3) Uani 1 1 d .
H97A H 0.2842 0.9109 0.4771 0.025 Uiso 1 1 calc R
H97B H 0.1453 0.8861 0.5190 0.025 Uiso 1 1 calc R
C98 C 0.20193(14) 0.79514(10) 0.40717(12) 0.0198(3) Uani 1 1 d .
H98A H 0.1242 0.7586 0.4166 0.024 Uiso 1 1 calc R
H98B H 0.1864 0.8228 0.3337 0.024 Uiso 1 1 calc R
C99 C 0.32975(15) 0.74296(10) 0.42275(12) 0.0211(3) Uani 1 1 d .
H99A H 0.3121 0.6822 0.3989 0.025 Uiso 1 1 calc R
H99B H 0.3951 0.7683 0.3793 0.025 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N C4 111.32(11)
C2 P Cl2 99.97(5)
C2 P Cl1 100.36(5)
Cl2 P Cl1 97.34(2)
N C1 C2 106.27(11)
N C1 C5 118.83(12)
C2 C1 C5 134.90(12)
C1 C2 C3 107.17(11)
C1 C2 P 127.53(10)
C3 C2 P 125.29(10)
C4 C3 C2 108.27(12)
C3 C4 N 106.97(12)
C3 C4 C9 131.43(12)
N C4 C9 121.58(12)
C1 C5 C6 112.04(11)
C1 C5 C7 109.77(11)
C6 C5 C7 108.18(11)
C1 C5 C8 109.14(11)
C6 C5 C8 108.45(11)
C7 C5 C8 109.22(12)
C4 C9 C12 109.04(11)
C4 C9 C10 110.04(11)
C12 C9 C10 108.98(11)
C4 C9 C11 110.32(11)
C12 C9 C11 109.22(11)
C10 C9 C11 109.22(12)
C99 O C96 109.51(11)
O C96 C97 105.55(12)
C96 C97 C98 101.72(12)
C99 C98 C97 102.07(12)
O C99 C98 106.07(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C1 1.3714(17)
N C4 1.3855(17)
P C2 1.7810(14)
P Cl2 2.0870(5)
P Cl1 2.0931(5)
C1 C2 1.3973(19)
C1 C5 1.5198(18)
C2 C3 1.4373(19)
C3 C4 1.3597(19)
C4 C9 1.5135(18)
C5 C6 1.5309(19)
C5 C7 1.5421(19)
C5 C8 1.5424(19)
C9 C12 1.5320(19)
C9 C10 1.5376(19)
C9 C11 1.5393(18)
O C99 1.4448(17)
O C96 1.4459(18)
C96 C97 1.518(2)
C97 C98 1.527(2)
C98 C99 1.514(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N H1 O 0.846(17) 2.033(17) 2.8775(15) 175.3(15)
C7 H7B O 0.98 2.52 3.4621(18) 161.6
C11 H11A O 0.98 2.61 3.5236(18) 155.3
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
C4 N C1 C2 0.44(14)
C4 N C1 C5 179.84(11)
N C1 C2 C3 -0.41(14)
C5 C1 C2 C3 -179.67(14)
N C1 C2 P 178.51(10)
C5 C1 C2 P -0.8(2)
Cl2 P C2 C1 -132.59(12)
Cl1 P C2 C1 127.98(12)
Cl2 P C2 C3 46.15(12)
Cl1 P C2 C3 -53.29(12)
C1 C2 C3 C4 0.25(15)
P C2 C3 C4 -178.70(10)
C2 C3 C4 N 0.01(15)
C2 C3 C4 C9 -178.44(13)
C1 N C4 C3 -0.28(15)
C1 N C4 C9 178.35(11)
N C1 C5 C6 170.26(12)
C2 C1 C5 C6 -10.6(2)
N C1 C5 C7 50.05(16)
C2 C1 C5 C7 -130.76(16)
N C1 C5 C8 -69.62(15)
C2 C1 C5 C8 109.57(17)
C3 C4 C9 C12 -3.5(2)
N C4 C9 C12 178.25(12)
C3 C4 C9 C10 115.99(16)
N C4 C9 C10 -62.27(16)
C3 C4 C9 C11 -123.43(16)
N C4 C9 C11 58.31(16)
C99 O C96 C97 -14.70(16)
O C96 C97 C98 33.02(15)
C96 C97 C98 C99 -38.16(14)
C96 O C99 C98 -10.13(16)
C97 C98 C99 O 30.39(15)
