#------------------------------------------------------------------------------
#$Date: 2016-03-24 00:01:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179521 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/18/4341817.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_4341817
loop_
_publ_author_name
'Kosnik, Stephanie C.'
'Farrar, Gregory J.'
'Norton, Erin L.'
'Cooper, Benjamin F. T.'
'Ellis, Bobby D.'
'Macdonald, Charles L. B.'
_publ_section_title
;
 Low-Valent Chemistry: An Alternative Approach to Phosphorus-Containing
 Oligomers.
;
_journal_name_full               'Inorganic chemistry'
_journal_page_first              141201074418004
_journal_paper_doi               10.1021/ic502229w
_journal_year                    2014
_chemical_formula_moiety         'C48 H40 Br Cu N2 P6, C H2 Cl2,'
_chemical_formula_sum            'C49 H42 Br Cl2 Cu N2 P6'
_chemical_formula_weight         1059.01
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 133.915(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   21.2636(18)
_cell_length_b                   10.1246(7)
_cell_length_c                   15.1840(12)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.05
_cell_measurement_theta_min      3.57
_cell_volume                     2354.8(4)
_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-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31574
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         3.567
_exptl_absorpt_coefficient_mu    1.667
_exptl_absorpt_correction_T_max  0.659
_exptl_absorpt_correction_T_min  0.537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2012'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.194
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 2800 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.152(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         6779
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0943P)²+0.2638P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1302
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                6356
_reflns_number_total             6779
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic502229w_si_004.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        2354.8(3)
_cod_database_code               4341817
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2012-9
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Br Br 0.0000 1.02627(9) 0.0000 0.0559(3) Uani 1 2 d S T P
Cu Cu 0.0000 1.25766(9) 0.0000 0.02134(16) Uani 1 2 d S T P
P1 P 0.14178(5) 1.50099(11) 0.12333(7) 0.01599(17) Uani 1 1 d . . .
P2 P 0.07619(6) 1.37072(11) -0.03211(8) 0.01878(19) Uani 1 1 d . . .
P3 P -0.03103(5) 1.50008(11) -0.17135(7) 0.01583(18) Uani 1 1 d . . .
N N 0.09108(19) 1.5652(3) 0.1552(3) 0.0174(5) Uani 1 1 d . . .
C11 C 0.2319(2) 1.3977(4) 0.2479(3) 0.0221(7) Uani 1 1 d . . .
C12 C 0.2212(3) 1.2637(5) 0.2521(4) 0.0345(9) Uani 1 1 d . . .
H12 H 0.1674 1.2224 0.1853 0.041 Uiso 1 1 calc R U .
C13 C 0.2883(4) 1.1894(6) 0.3531(5) 0.0438(11) Uani 1 1 d . . .
H13 H 0.2806 1.0972 0.3543 0.053 Uiso 1 1 calc R U .
C14 C 0.3661(3) 1.2478(6) 0.4516(4) 0.0418(11) Uani 1 1 d . . .
H14 H 0.4108 1.1969 0.5220 0.050 Uiso 1 1 calc R U .
C15 C 0.3790(3) 1.3814(6) 0.4482(4) 0.0401(11) Uani 1 1 d . . .
H15 H 0.4336 1.4212 0.5147 0.048 Uiso 1 1 calc R U .
C16 C 0.3121(3) 1.4565(5) 0.3475(4) 0.0307(8) Uani 1 1 d . . .
H16 H 0.3206 1.5482 0.3459 0.037 Uiso 1 1 calc R U .
C21 C 0.1934(2) 1.6385(5) 0.1176(3) 0.0228(7) Uani 1 1 d . . .
C22 C 0.2471(3) 1.6102(5) 0.0965(4) 0.0349(10) Uani 1 1 d . . .
H22 H 0.2552 1.5216 0.0856 0.042 Uiso 1 1 calc R U .
C23 C 0.2873(4) 1.7112(8) 0.0917(5) 0.0531(17) Uani 1 1 d . . .
H23 H 0.3231 1.6927 0.0770 0.064 Uiso 1 1 calc R U .
C24 C 0.2759(4) 1.8406(7) 0.1082(5) 0.0539(18) Uani 1 1 d . . .
H24 H 0.3049 1.9103 0.1065 0.065 Uiso 1 1 calc R U .
C25 C 0.2222(4) 1.8687(6) 0.1272(6) 0.0526(15) Uani 1 1 d . . .
H25 H 0.2137 1.9576 0.1369 0.063 Uiso 1 1 calc R U .
C26 C 0.1805(3) 1.7662(5) 0.1322(4) 0.0370(9) Uani 1 1 d . . .
H26 H 0.1438 1.7849 0.1455 0.044 Uiso 1 1 calc R U .
C31 C -0.0960(3) 1.3988(4) -0.3093(3) 0.0234(7) Uani 1 1 d . . .
C32 C -0.0798(3) 1.2661(5) -0.3084(4) 0.0425(12) Uani 1 1 d . . .
H32 H -0.0305 1.2245 -0.2346 0.051 Uiso 1 1 calc R U .
C33 C -0.1368(5) 1.1936(6) -0.4180(5) 0.0552(16) Uani 1 1 d . . .
H33 H -0.1259 1.1025 -0.4176 0.066 Uiso 1 1 calc R U .
C34 C -0.2072(4) 1.2523(6) -0.5245(4) 0.0450(12) Uani 1 1 d . . .
H34 H -0.2450 1.2024 -0.5980 0.054 Uiso 1 1 calc R U .
C35 C -0.2235(4) 1.3827(6) -0.5255(4) 0.0450(13) Uani 1 1 d . . .
H35 H -0.2731 1.4231 -0.5998 0.054 Uiso 1 1 calc R U .
C36 C -0.1681(3) 1.4573(5) -0.4186(4) 0.0364(10) Uani 1 1 d . . .
H36 H -0.1796 1.5485 -0.4205 0.044 Uiso 1 1 calc R U .
C41 C 0.0076(2) 1.6372(5) -0.1993(3) 0.0220(6) Uani 1 1 d . . .
C42 C 0.0514(3) 1.6113(6) -0.2359(4) 0.0362(11) Uani 1 1 d . . .
H42 H 0.0581 1.5230 -0.2495 0.043 Uiso 1 1 calc R U .
C43 C 0.0852(3) 1.7158(8) -0.2521(5) 0.0513(17) Uani 1 1 d . . .
H43 H 0.1153 1.6988 -0.2764 0.062 Uiso 1 1 calc R U .
C44 C 0.0750(4) 1.8440(7) -0.2330(5) 0.0508(17) Uani 1 1 d . . .
H44 H 0.0980 1.9148 -0.2445 0.061 Uiso 1 1 calc R U .
C45 C 0.0318(5) 1.8705(6) -0.1975(6) 0.0522(15) Uani 1 1 d . . .
H45 H 0.0249 1.9590 -0.1847 0.063 Uiso 1 1 calc R U .
C46 C -0.0018(3) 1.7655(5) -0.1802(4) 0.0366(9) Uani 1 1 d . . .
H46 H -0.0314 1.7832 -0.1551 0.044 Uiso 1 1 calc R U .
Cl1 Cl 0.5000 0.9555(4) 0.5000 0.178(3) Uani 1 2 d DS TU P
Cl2 Cl 0.5000 0.6783(5) 0.5000 0.228(5) Uani 1 2 d DS TU P
C51 C 0.4600(18) 0.8169(3) 0.461(5) 0.176(14) Uani 0.5 1 d D U P
H51A H 0.4201 0.8169 0.4730 0.212 Uiso 0.5 1 calc R U P
H51B H 0.4217 0.8169 0.3708 0.212 Uiso 0.5 1 calc R U 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'
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
P2 Cu P2 120.17(5) 2 .
P2 Cu Br 119.92(3) 2 .
P2 Cu Br 119.91(3) . .
N P1 C21 105.13(18) . .
N P1 C11 111.38(16) . .
C21 P1 C11 104.77(17) . .
N P1 P2 121.29(11) . .
C21 P1 P2 111.67(13) . .
C11 P1 P2 101.58(13) . .
P1 P2 P3 98.15(5) . .
P1 P2 Cu 95.06(4) . .
P3 P2 Cu 95.09(4) . .
N P3 C41 105.11(18) 2 .
N P3 C31 110.95(17) 2 .
C41 P3 C31 105.53(18) . .
N P3 P2 120.74(11) 2 .
C41 P3 P2 110.56(12) . .
C31 P3 P2 103.10(14) . .
P1 N P3 131.1(2) . 2
C12 C11 C16 118.7(4) . .
C12 C11 P1 121.5(3) . .
C16 C11 P1 119.5(3) . .
C11 C12 C13 120.5(4) . .
C11 C12 H12 119.8 . .
C13 C12 H12 119.8 . .
C14 C13 C12 120.6(5) . .
C14 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
C13 C14 C15 119.9(4) . .
C13 C14 H14 120.0 . .
C15 C14 H14 120.0 . .
C16 C15 C14 119.8(5) . .
C16 C15 H15 120.1 . .
C14 C15 H15 120.1 . .
C15 C16 C11 120.4(5) . .
C15 C16 H16 119.8 . .
C11 C16 H16 119.8 . .
C26 C21 C22 120.8(4) . .
C26 C21 P1 121.3(3) . .
C22 C21 P1 117.9(4) . .
C23 C22 C21 119.6(6) . .
C23 C22 H22 120.2 . .
C21 C22 H22 120.2 . .
C22 C23 C24 120.3(6) . .
C22 C23 H23 119.9 . .
C24 C23 H23 119.9 . .
C23 C24 C25 120.2(5) . .
C23 C24 H24 119.9 . .
C25 C24 H24 119.9 . .
C24 C25 C26 120.2(6) . .
C24 C25 H25 119.9 . .
C26 C25 H25 119.9 . .
C21 C26 C25 118.9(5) . .
C21 C26 H26 120.5 . .
C25 C26 H26 120.5 . .
C32 C31 C36 119.1(4) . .
C32 C31 P3 123.3(3) . .
C36 C31 P3 117.5(3) . .
C31 C32 C33 119.4(5) . .
C31 C32 H32 120.3 . .
C33 C32 H32 120.3 . .
C34 C33 C32 120.9(5) . .
C34 C33 H33 119.6 . .
C32 C33 H33 119.6 . .
C33 C34 C35 119.9(5) . .
C33 C34 H34 120.1 . .
C35 C34 H34 120.1 . .
C34 C35 C36 120.6(5) . .
C34 C35 H35 119.7 . .
C36 C35 H35 119.7 . .
C31 C36 C35 120.1(5) . .
C31 C36 H36 119.9 . .
C35 C36 H36 119.9 . .
C46 C41 C42 119.7(4) . .
C46 C41 P3 121.2(3) . .
C42 C41 P3 119.0(4) . .
C43 C42 C41 119.5(5) . .
C43 C42 H42 120.2 . .
C41 C42 H42 120.2 . .
C44 C43 C42 120.2(5) . .
C44 C43 H43 119.9 . .
C42 C43 H43 119.9 . .
C45 C44 C43 120.7(5) . .
C45 C44 H44 119.7 . .
C43 C44 H44 119.7 . .
C44 C45 C46 119.4(6) . .
C44 C45 H45 120.3 . .
C46 C45 H45 120.3 . .
C41 C46 C45 120.4(5) . .
C41 C46 H46 119.8 . .
C45 C46 H46 119.8 . .
C51 Cl1 C51 47(2) . 2_656
C51 Cl2 C51 47(2) 2_656 .
Cl2 C51 Cl1 133(2) . .
Cl2 C51 H51A 104.0 . .
Cl1 C51 H51A 104.0 . .
Cl2 C51 H51B 104.0 . .
Cl1 C51 H51B 104.0 . .
H51A C51 H51B 105.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br Cu 2.3427(8) .
Cu P2 2.2952(10) 2
Cu P2 2.2953(10) .
P1 N 1.595(3) .
P1 C21 1.812(4) .
P1 C11 1.820(4) .
P1 P2 2.1654(12) .
P2 P3 2.1672(12) .
P3 N 1.600(3) 2
P3 C41 1.808(4) .
P3 C31 1.826(4) .
N P3 1.600(3) 2
C11 C12 1.385(6) .
C11 C16 1.405(6) .
C12 C13 1.385(6) .
C12 H12 0.9500 .
C13 C14 1.375(8) .
C13 H13 0.9500 .
C14 C15 1.388(9) .
C14 H14 0.9500 .
C15 C16 1.386(6) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 C26 1.372(7) .
C21 C22 1.413(6) .
C22 C23 1.366(7) .
C22 H22 0.9500 .
C23 C24 1.386(11) .
C23 H23 0.9500 .
C24 C25 1.388(11) .
C24 H24 0.9500 .
C25 C26 1.400(7) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C31 C32 1.385(6) .
C31 C36 1.388(6) .
C32 C33 1.406(6) .
C32 H32 0.9500 .
C33 C34 1.361(8) .
C33 H33 0.9500 .
C34 C35 1.362(9) .
C34 H34 0.9500 .
C35 C36 1.394(7) .
C35 H35 0.9500 .
C36 H36 0.9500 .
C41 C46 1.376(7) .
C41 C42 1.400(6) .
C42 C43 1.394(7) .
C42 H42 0.9500 .
C43 C44 1.379(11) .
C43 H43 0.9500 .
C44 C45 1.376(11) .
C44 H44 0.9500 .
C45 C46 1.404(7) .
C45 H45 0.9500 .
C46 H46 0.9500 .
Cl1 C51 1.531(12) .
Cl1 C51 1.531(12) 2_656
Cl2 C51 1.531(12) 2_656
Cl2 C51 1.531(12) .
C51 H51A 0.9900 .
C51 H51B 0.9900 .
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
_geom_hbond_site_symmetry_A
C46 H46 Br 0.95 3.14 3.783(5) 126.3 1_565
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
C21 P1 N P3 178.7(2) . 2
C11 P1 N P3 -68.3(3) . 2
P2 P1 N P3 51.0(3) . 2
N P1 C11 C12 92.0(4) . .
C21 P1 C11 C12 -154.9(4) . .
P2 P1 C11 C12 -38.5(4) . .
N P1 C11 C16 -82.4(3) . .
C21 P1 C11 C16 30.8(4) . .
P2 P1 C11 C16 147.1(3) . .
C16 C11 C12 C13 0.3(7) . .
P1 C11 C12 C13 -174.1(4) . .
C11 C12 C13 C14 1.2(8) . .
C12 C13 C14 C15 -2.7(8) . .
C13 C14 C15 C16 2.7(8) . .
C14 C15 C16 C11 -1.2(7) . .
C12 C11 C16 C15 -0.3(6) . .
P1 C11 C16 C15 174.3(4) . .
N P1 C21 C26 -3.5(4) . .
C11 P1 C21 C26 -121.0(3) . .
P2 P1 C21 C26 129.8(3) . .
N P1 C21 C22 177.1(3) . .
C11 P1 C21 C22 59.6(3) . .
P2 P1 C21 C22 -49.6(3) . .
C26 C21 C22 C23 0.6(7) . .
P1 C21 C22 C23 -179.9(4) . .
C21 C22 C23 C24 0.4(8) . .
C22 C23 C24 C25 -1.3(9) . .
C23 C24 C25 C26 1.2(9) . .
C22 C21 C26 C25 -0.7(7) . .
P1 C21 C26 C25 179.8(4) . .
C24 C25 C26 C21 -0.2(8) . .
N P3 C31 C32 -122.9(4) 2 .
C41 P3 C31 C32 123.8(4) . .
P2 P3 C31 C32 7.8(4) . .
N P3 C31 C36 53.4(4) 2 .
C41 P3 C31 C36 -60.0(4) . .
P2 P3 C31 C36 -176.0(3) . .
C36 C31 C32 C33 -0.4(8) . .
P3 C31 C32 C33 175.8(5) . .
C31 C32 C33 C34 0.3(10) . .
C32 C33 C34 C35 -0.5(10) . .
C33 C34 C35 C36 0.6(10) . .
C32 C31 C36 C35 0.6(7) . .
P3 C31 C36 C35 -175.8(4) . .
C34 C35 C36 C31 -0.7(9) . .
N P3 C41 C46 12.5(4) 2 .
C31 P3 C41 C46 129.9(3) . .
P2 P3 C41 C46 -119.3(3) . .
N P3 C41 C42 -170.3(3) 2 .
C31 P3 C41 C42 -53.0(4) . .
P2 P3 C41 C42 57.8(3) . .
C46 C41 C42 C43 0.2(6) . .
P3 C41 C42 C43 -177.0(3) . .
C41 C42 C43 C44 -0.4(7) . .
C42 C43 C44 C45 0.2(8) . .
C43 C44 C45 C46 0.2(8) . .
C42 C41 C46 C45 0.2(7) . .
P3 C41 C46 C45 177.3(4) . .
C44 C45 C46 C41 -0.4(8) . .
C51 Cl2 C51 Cl1 0.000(7) 2_656 .
C51 Cl1 C51 Cl2 0.000(8) 2_656 .
