#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/12/2211298.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_2211298
loop_
_publ_author_name
'Habibi, Mohammad Hossein'
'Montazerozohori, Morteza'
'Barati, Kazem'
'Lee, Uk'
'Choi, Jong-Ha'
_publ_section_title
'[N,N'-Bis(2-chlorobenzylidene)ethylenediamine]bromo(triphenylphosphine)copper(I)'
_journal_coeditor_code           BI2099
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m3392
_journal_page_last               m3394
_journal_paper_doi               10.1107/S1600536806048239
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Cu Br (C16 H14 Cl2 N2) (C18 H15 P)]'
_chemical_formula_moiety         'C34 H29 Br Cl2 Cu N2 P'
_chemical_formula_sum            'C34 H29 Br Cl2 Cu N2 P'
_chemical_formula_weight         710.91
_chemical_name_systematic
;
Bromo
bis[N,N'-(2-chlorobenzylidene)ethylenediamine(triphenylphosphine)]copper(I)
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.4630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3050(5)
_cell_length_b                   21.6710(10)
_cell_length_c                   14.0214(7)
_cell_measurement_reflns_used    6534
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.24
_cell_volume                     3057.5(3)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
ORTEP III (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18624
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.276
_exptl_absorpt_correction_T_max  0.601
_exptl_absorpt_correction_T_min  0.479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            'pale blue'
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.356
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         6634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0330
_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)+(0.0362P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                4939
_reflns_number_total             6634
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2099.cif
_cod_data_source_block           I
_cod_original_cell_volume        3057.6(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2211298
_cod_database_fobs_code          2211298
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_type_symbol
_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
Br Br 0.92465(3) 0.213261(13) 0.26311(2) 0.02797(8) Uani d . 1
Cu Cu 0.70949(3) 0.157059(14) 0.22960(2) 0.02159(9) Uani d . 1
P P 0.64647(6) 0.09115(3) 0.33018(5) 0.01932(14) Uani d . 1
Cl Cl1 0.29271(8) 0.31235(4) 0.31605(7) 0.0468(2) Uani d . 1
Cl Cl2 0.63752(9) -0.03380(4) -0.05972(6) 0.0504(2) Uani d . 1
N N1 0.6577(2) 0.13903(10) 0.07872(15) 0.0229(5) Uani d . 1
N N2 0.5909(2) 0.23711(10) 0.19021(15) 0.0245(5) Uani d . 1
C C1 0.5513(3) 0.18280(12) 0.0350(2) 0.0303(6) Uani d . 1
H H1A 0.4660 0.1673 0.0430 0.036 Uiso calc R 1
H H1B 0.5480 0.1871 -0.0344 0.036 Uiso calc R 1
C C2 0.5790(3) 0.24477(12) 0.08462(19) 0.0294(6) Uani d . 1
H H2A 0.6608 0.2618 0.0721 0.035 Uiso calc R 1
H H2B 0.5073 0.2732 0.0588 0.035 Uiso calc R 1
C C3 0.5347(3) 0.27632(13) 0.2354(2) 0.0311(7) Uani d . 1
H H3 0.4812 0.3064 0.1994 0.037 Uiso calc R 1
C C4 0.5508(3) 0.27606(12) 0.3431(2) 0.0282(6) Uani d . 1
C C5 0.4471(3) 0.29219(12) 0.3878(2) 0.0304(6) Uani d . 1
C C6 0.4611(3) 0.29158(13) 0.4879(2) 0.0378(7) Uani d . 1
H H6 0.3900 0.3021 0.5157 0.045 Uiso calc R 1
C C7 0.5818(3) 0.27518(14) 0.5461(2) 0.0391(8) Uani d . 1
H H7 0.5922 0.2744 0.6136 0.047 Uiso calc R 1
C C8 0.6874(3) 0.25995(14) 0.5043(2) 0.0367(7) Uani d . 1
H H8 0.7688 0.2493 0.5438 0.044 Uiso calc R 1
C C9 0.6722(3) 0.26054(13) 0.4037(2) 0.0307(6) Uani d . 1
H H9 0.7439 0.2505 0.3762 0.037 Uiso calc R 1
C C10 0.6832(3) 0.09578(12) 0.02426(19) 0.0291(6) Uani d . 1
H H10 0.6319 0.0925 -0.0388 0.035 Uiso calc R 1
C C11 0.7905(3) 0.05068(12) 0.05674(18) 0.0266(6) Uani d . 1
C C12 0.9070(3) 0.06782(13) 0.12243(19) 0.0288(6) Uani d . 1
H H12 0.9163 0.1080 0.1462 0.035 Uiso calc R 1
C C13 1.0087(3) 0.02577(14) 0.1526(2) 0.0341(7) Uani d . 1
H H13 1.0867 0.0379 0.1954 0.041 Uiso calc R 1
C C14 0.9939(3) -0.03432(14) 0.1189(2) 0.0409(8) Uani d . 1
H H14 1.0614 -0.0628 0.1404 0.049 Uiso calc R 1
C C15 0.8808(3) -0.05251(14) 0.0543(2) 0.0386(8) Uani d . 1
H H15 0.8714 -0.0930 0.0320 0.046 Uiso calc R 1
C C16 0.7807(3) -0.00993(13) 0.02254(19) 0.0320(7) Uani d . 1
C C17 0.5968(3) 0.01218(12) 0.28885(17) 0.0221(6) Uani d . 1
C C18 0.4829(3) -0.01602(13) 0.30571(19) 0.0294(6) Uani d . 1
H H18 0.4242 0.0064 0.3341 0.035 Uiso calc R 1
C C19 0.4559(3) -0.07734(14) 0.2805(2) 0.0352(7) Uani d . 1
H H19 0.3788 -0.0957 0.2915 0.042 Uiso calc R 1
C C20 0.5433(3) -0.11115(13) 0.2392(2) 0.0381(8) Uani d . 1
H H20 0.5258 -0.1524 0.2234 0.046 Uiso calc R 1
C C21 0.6563(3) -0.08376(13) 0.2215(2) 0.0370(7) Uani d . 1
H H21 0.7150 -0.1064 0.1934 0.044 Uiso calc R 1
C C22 0.6823(3) -0.02199(12) 0.24584(19) 0.0285(6) Uani d . 1
H H22 0.7581 -0.0034 0.2330 0.034 Uiso calc R 1
C C23 0.7657(2) 0.07320(11) 0.44385(17) 0.0197(5) Uani d . 1
C C24 0.8871(3) 0.10405(12) 0.46455(18) 0.0250(6) Uani d . 1
H H24 0.9046 0.1350 0.4232 0.030 Uiso calc R 1
C C25 0.9819(3) 0.08835(13) 0.54725(19) 0.0311(7) Uani d . 1
H H25 1.0630 0.1089 0.5609 0.037 Uiso calc R 1
C C26 0.9576(3) 0.04291(13) 0.6090(2) 0.0331(7) Uani d . 1
H H26 1.0217 0.0330 0.6644 0.040 Uiso calc R 1
C C27 0.8372(3) 0.01175(13) 0.5889(2) 0.0335(7) Uani d . 1
H H27 0.8202 -0.0189 0.6310 0.040 Uiso calc R 1
C C28 0.7425(3) 0.02640(12) 0.50636(19) 0.0284(6) Uani d . 1
H H28 0.6626 0.0049 0.4923 0.034 Uiso calc R 1
C C29 0.4961(2) 0.11774(11) 0.36652(18) 0.0206(5) Uani d . 1
C C30 0.3872(3) 0.13199(12) 0.29103(19) 0.0250(6) Uani d . 1
H H30 0.3959 0.1297 0.2265 0.030 Uiso calc R 1
C C31 0.2671(3) 0.14942(12) 0.3112(2) 0.0275(6) Uani d . 1
H H31 0.1951 0.1578 0.2603 0.033 Uiso calc R 1
C C32 0.2537(3) 0.15444(13) 0.4070(2) 0.0322(7) Uani d . 1
H H32 0.1730 0.1665 0.4206 0.039 Uiso calc R 1
C C33 0.3603(3) 0.14151(13) 0.4819(2) 0.0333(7) Uani d . 1
H H33 0.3514 0.1449 0.5463 0.040 Uiso calc R 1
C C34 0.4815(3) 0.12330(12) 0.46207(19) 0.0270(6) Uani d . 1
H H34 0.5531 0.1148 0.5133 0.032 Uiso calc R 1
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_publ_flag
N1 Cu N2 83.31(8) yes
N1 Cu P 118.54(6) yes
N2 Cu P 117.61(7) yes
N1 Cu Br 107.68(6) yes
N2 Cu Br 95.09(6) yes
P Cu Br 124.86(2) yes
Cu N1 C10 134.4(2) ?
Cu N1 C1 107.6(2) ?
Cu N2 C3 135.6(2) ?
Cu N2 C2 105.8(2) ?
C29 P C23 105.90(10) ?
C29 P C17 100.70(10) ?
C23 P C17 99.50(10) ?
C29 P Cu 111.07(8) ?
C23 P Cu 117.38(9) ?
C17 P Cu 120.09(9) ?
C10 N1 C1 117.0(2) ?
C3 N2 C2 118.6(2) ?
N1 C1 C2 109.2(2) ?
N1 C1 H1A 109.8 ?
C2 C1 H1A 109.8 ?
N1 C1 H1B 109.8 ?
C2 C1 H1B 109.8 ?
H1A C1 H1B 108.3 ?
N2 C2 C1 109.3(2) ?
N2 C2 H2A 109.8 ?
C1 C2 H2A 109.8 ?
N2 C2 H2B 109.8 ?
C1 C2 H2B 109.8 ?
H2A C2 H2B 108.3 ?
N2 C3 C4 122.8(2) ?
N2 C3 H3 118.6 ?
C4 C3 H3 118.6 ?
C9 C4 C5 117.5(3) ?
C9 C4 C3 120.7(3) ?
C5 C4 C3 121.9(3) ?
C6 C5 C4 122.2(3) ?
C6 C5 Cl1 118.1(2) ?
C4 C5 Cl1 119.7(2) ?
C7 C6 C5 119.2(3) ?
C7 C6 H6 120.4 ?
C5 C6 H6 120.4 ?
C6 C7 C8 120.1(3) ?
C6 C7 H7 119.9 ?
C8 C7 H7 119.9 ?
C7 C8 C9 120.2(3) ?
C7 C8 H8 119.9 ?
C9 C8 H8 119.9 ?
C8 C9 C4 120.8(3) ?
C8 C9 H9 119.6 ?
C4 C9 H9 119.6 ?
N1 C10 C11 122.8(2) ?
N1 C10 H10 118.6 ?
C11 C10 H10 118.6 ?
C16 C11 C12 117.8(3) ?
C16 C11 C10 121.7(2) ?
C12 C11 C10 120.6(2) ?
C13 C12 C11 120.9(3) ?
C13 C12 H12 119.6 ?
C11 C12 H12 119.6 ?
C14 C13 C12 119.6(3) ?
C14 C13 H13 120.2 ?
C12 C13 H13 120.2 ?
C15 C14 C13 120.9(3) ?
C15 C14 H14 119.6 ?
C13 C14 H14 119.6 ?
C14 C15 C16 119.3(3) ?
C14 C15 H15 120.4 ?
C16 C15 H15 120.4 ?
C15 C16 C11 121.6(3) ?
C15 C16 Cl2 118.7(2) ?
C11 C16 Cl2 119.7(2) ?
C22 C17 C18 118.7(2) ?
C22 C17 P 118.3(2) ?
C18 C17 P 122.9(2) ?
C19 C18 C17 120.6(3) ?
C19 C18 H18 119.7 ?
C17 C18 H18 119.7 ?
C20 C19 C18 120.1(3) ?
C20 C19 H19 120.0 ?
C18 C19 H19 120.0 ?
C21 C20 C19 120.0(3) ?
C21 C20 H20 120.0 ?
C19 C20 H20 120.0 ?
C20 C21 C22 119.7(3) ?
C20 C21 H21 120.1 ?
C22 C21 H21 120.1 ?
C17 C22 C21 120.9(3) ?
C17 C22 H22 119.6 ?
C21 C22 H22 119.6 ?
C24 C23 C28 119.1(2) ?
C24 C23 P 118.89(19) ?
C28 C23 P 121.83(19) ?
C25 C24 C23 119.7(2) ?
C25 C24 H24 120.2 ?
C23 C24 H24 120.2 ?
C26 C25 C24 120.8(3) ?
C26 C25 H25 119.6 ?
C24 C25 H25 119.6 ?
C25 C26 C27 120.0(2) ?
C25 C26 H26 120.0 ?
C27 C26 H26 120.0 ?
C28 C27 C26 119.8(3) ?
C28 C27 H27 120.1 ?
C26 C27 H27 120.1 ?
C27 C28 C23 120.6(3) ?
C27 C28 H28 119.7 ?
C23 C28 H28 119.7 ?
C34 C29 C30 118.4(2) ?
C34 C29 P 124.95(19) ?
C30 C29 P 116.6(2) ?
C31 C30 C29 120.8(3) ?
C31 C30 H30 119.6 ?
C29 C30 H30 119.6 ?
C30 C31 C32 120.2(2) ?
C30 C31 H31 119.9 ?
C32 C31 H31 119.9 ?
C33 C32 C31 119.7(3) ?
C33 C32 H32 120.2 ?
C31 C32 H32 120.2 ?
C32 C33 C34 120.5(3) ?
C32 C33 H33 119.8 ?
C34 C33 H33 119.8 ?
C29 C34 C33 120.4(2) ?
C29 C34 H34 119.8 ?
C33 C34 H34 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu Br 2.4841(4) yes
Cu N1 2.104(2) yes
Cu N2 2.126(2) yes
Cu P 2.2014(7) yes
N1 C1 1.479(3) ?
N1 C10 1.272(3) ?
N2 C2 1.469(3) ?
N2 C3 1.272(3) ?
P C29 1.826(3) ?
P C23 1.832(2) ?
P C17 1.844(3) ?
Cl1 C5 1.744(3) ?
Cl2 C16 1.744(3) ?
C1 C2 1.512(4) ?
C1 H1A 0.970 ?
C1 H1B 0.970 ?
C2 H2A 0.970 ?
C2 H2B 0.970 ?
C3 C4 1.483(4) ?
C3 H3 0.930 ?
C4 C9 1.393(4) ?
C4 C5 1.394(4) ?
C5 C6 1.380(4) ?
C6 C7 1.379(4) ?
C6 H6 0.930 ?
C7 C8 1.383(4) ?
C7 H7 0.930 ?
C8 C9 1.385(4) ?
C8 H8 0.930 ?
C9 H9 0.930 ?
C10 C11 1.472(4) ?
C10 H10 0.930 ?
C11 C16 1.395(4) ?
C11 C12 1.396(4) ?
C12 C13 1.385(4) ?
C12 H12 0.930 ?
C13 C14 1.382(4) ?
C13 H13 0.930 ?
C14 C15 1.371(4) ?
C14 H14 0.930 ?
C15 C16 1.384(4) ?
C15 H15 0.930 ?
C17 C22 1.385(4) ?
C17 C18 1.388(4) ?
C18 C19 1.388(4) ?
C18 H18 0.930 ?
C19 C20 1.382(4) ?
C19 H19 0.930 ?
C20 C21 1.376(4) ?
C20 H20 0.930 ?
C21 C22 1.393(4) ?
C21 H21 0.930 ?
C22 H22 0.930 ?
C23 C24 1.393(3) ?
C23 C28 1.394(3) ?
C24 C25 1.388(3) ?
C24 H24 0.930 ?
C25 C26 1.370(4) ?
C25 H25 0.930 ?
C26 C27 1.387(4) ?
C26 H26 0.930 ?
C27 C28 1.380(3) ?
C27 H27 0.930 ?
C28 H28 0.930 ?
C29 C34 1.385(4) ?
C29 C30 1.401(3) ?
C30 C31 1.380(4) ?
C30 H30 0.930 ?
C31 C32 1.383(4) ?
C31 H31 0.930 ?
C32 C33 1.375(4) ?
C32 H32 0.930 ?
C33 C34 1.395(4) ?
C33 H33 0.930 ?
C34 H34 0.930 ?
