#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/65/2236518.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_2236518
loop_
_publ_author_name
'Barnard, Nicola I.'
'Hill, Tania N.'
_publ_section_title
;
 Bis(diphenyl-p-tolylphosphane-κP)(2-hydroxy-3,5,7-bromocyclohepta-2,4,6-trienonato-κ²O,O')copper(I)
;
_journal_coeditor_code           NG5299
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1354
_journal_page_last               m1355
_journal_paper_doi               10.1107/S1600536812042286
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Cu (C7 H2 Br3 O2) (C19 H17 P)2]'
_chemical_formula_moiety         'C45 H36 Br3 Cu O2 P2'
_chemical_formula_sum            'C45 H36 Br3 Cu O2 P2'
_chemical_formula_weight         973.95
_chemical_name_systematic
;
Bis(diphenyl-p-tolylphosphane-κP)(2-hydroxy-3,5,7-\
bromocyclohepta-2,4,6-trienonato-κ²O,O')copper(I)
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.862(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4522(8)
_cell_length_b                   13.9073(8)
_cell_length_c                   19.3269(10)
_cell_measurement_reflns_used    8436
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.31
_cell_volume                     4032.4(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker X8 APEXII 4K Kappa CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27602
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.631
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.508
_refine_diff_density_min         -1.57
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         5022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0661P)²+16.6643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1302
_reflns_number_gt                3970
_reflns_number_total             5022
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ng5299.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2236518
_cod_database_fobs_code          2236518
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_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
C C2 0.5382(2) 0.6353(3) 0.28258(18) 0.0213(7) Uani d . 1
C C3 0.5717(2) 0.7199(3) 0.32159(19) 0.0230(7) Uani d . 1
C C4 0.5556(2) 0.8171(3) 0.3086(2) 0.0294(8) Uani d . 1
H H4 0.5867 0.8596 0.3446 0.035 Uiso calc R 1
C C5 0.5 0.8599(3) 0.25 0.0295(12) Uani d S 1
C C111 0.3102(2) 0.3211(3) 0.25441(19) 0.0242(7) Uani d . 1
C C112 0.2526(2) 0.3880(3) 0.2148(2) 0.0309(8) Uani d . 1
H H112 0.2662 0.4546 0.2202 0.037 Uiso calc R 1
C C113 0.1744(3) 0.3578(4) 0.1667(2) 0.0373(10) Uani d . 1
H H113 0.1339 0.4041 0.1411 0.045 Uiso calc R 1
C C114 0.1562(3) 0.2615(4) 0.1565(2) 0.0375(10) Uani d . 1
H H114 0.1041 0.2411 0.1227 0.045 Uiso calc R 1
C C115 0.2132(3) 0.1946(3) 0.1954(2) 0.0384(10) Uani d . 1
H H115 0.2003 0.128 0.1883 0.046 Uiso calc R 1
C C116 0.2898(2) 0.2235(3) 0.2451(2) 0.0310(8) Uani d . 1
H H116 0.3281 0.1769 0.2725 0.037 Uiso calc R 1
C C121 0.4606(2) 0.2639(2) 0.36831(19) 0.0221(7) Uani d . 1
C C122 0.5385(3) 0.2234(3) 0.3588(2) 0.0317(8) Uani d . 1
H H122 0.5645 0.2472 0.3223 0.038 Uiso calc R 1
C C123 0.5799(3) 0.1478(3) 0.4021(3) 0.0432(11) Uani d . 1
H H123 0.6334 0.1205 0.3949 0.052 Uiso calc R 1
C C124 0.5423(3) 0.1126(3) 0.4559(2) 0.0412(10) Uani d . 1
H H124 0.57 0.0613 0.4856 0.049 Uiso calc R 1
C C125 0.4650(3) 0.1526(3) 0.4655(3) 0.0470(12) Uani d . 1
H H125 0.4394 0.1292 0.5023 0.056 Uiso calc R 1
C C126 0.4237(3) 0.2272(3) 0.4219(3) 0.0391(10) Uani d . 1
H H126 0.3697 0.2535 0.4288 0.047 Uiso calc R 1
C C131 0.3738(2) 0.4421(2) 0.37497(17) 0.0202(7) Uani d . 1
C C132 0.2920(2) 0.4256(3) 0.39248(19) 0.0236(7) Uani d . 1
H H132 0.2525 0.3778 0.3677 0.028 Uiso calc R 1
C C133 0.2690(2) 0.4791(3) 0.4460(2) 0.0277(8) Uani d . 1
H H133 0.2138 0.4667 0.4579 0.033 Uiso calc R 1
C C134 0.3244(3) 0.5498(3) 0.4823(2) 0.0303(8) Uani d . 1
C C135 0.4049(2) 0.5684(3) 0.46311(19) 0.0263(7) Uani d . 1
H H135 0.443 0.6183 0.4864 0.032 Uiso calc R 1
C C136 0.4292(2) 0.5143(3) 0.41023(18) 0.0222(7) Uani d . 1
H H136 0.4841 0.527 0.3981 0.027 Uiso calc R 1
C C137 0.3016(3) 0.6032(4) 0.5422(3) 0.0512(13) Uani d . 1
H H13A 0.3485 0.6502 0.5612 0.077 Uiso calc R 1
H H13B 0.2964 0.5579 0.5798 0.077 Uiso calc R 1
H H13C 0.2447 0.6368 0.5249 0.077 Uiso calc R 1
O O2 0.56859(15) 0.55420(17) 0.30362(13) 0.0227(5) Uani d . 1
P P1 0.41329(5) 0.36611(6) 0.31230(5) 0.01920(18) Uani d . 1
Cu Cu1 0.5 0.43613(4) 0.25 0.01987(15) Uani d S 1
Br Br1 0.65536(3) 0.69166(3) 0.40942(2) 0.03295(13) Uani d . 1
Br Br2 0.5 0.99600(5) 0.25 0.0638(3) Uani d S 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O2 C2 C3 . . 120.7(3)
O2 C2 C2 . 2_655 115.45(19)
C3 C2 C2 . 2_655 123.7(2)
C4 C3 C2 . . 133.0(3)
C4 C3 Br1 . . 114.5(3)
C2 C3 Br1 . . 112.5(3)
C5 C4 C3 . . 128.1(4)
C5 C4 H4 . . 115.9
C3 C4 H4 . . 115.9
C4 C5 C4 2_655 . 129.0(5)
C4 C5 Br2 2_655 . 115.5(2)
C4 C5 Br2 . . 115.5(2)
C112 C111 C116 . . 119.1(3)
C112 C111 P1 . . 117.4(3)
C116 C111 P1 . . 123.4(3)
C111 C112 C113 . . 120.2(4)
C111 C112 H112 . . 119.9
C113 C112 H112 . . 119.9
C114 C113 C112 . . 120.2(4)
C114 C113 H113 . . 119.9
C112 C113 H113 . . 119.9
C113 C114 C115 . . 119.9(4)
C113 C114 H114 . . 120.1
C115 C114 H114 . . 120.1
C114 C115 C116 . . 120.6(4)
C114 C115 H115 . . 119.7
C116 C115 H115 . . 119.7
C115 C116 C111 . . 119.9(4)
C115 C116 H116 . . 120.1
C111 C116 H116 . . 120.1
C122 C121 C126 . . 118.3(3)
C122 C121 P1 . . 118.4(3)
C126 C121 P1 . . 123.2(3)
C121 C122 C123 . . 121.0(4)
C121 C122 H122 . . 119.5
C123 C122 H122 . . 119.5
C122 C123 C124 . . 119.9(4)
C122 C123 H123 . . 120.1
C124 C123 H123 . . 120.1
C125 C124 C123 . . 119.3(4)
C125 C124 H124 . . 120.3
C123 C124 H124 . . 120.3
C124 C125 C126 . . 120.6(4)
C124 C125 H125 . . 119.7
C126 C125 H125 . . 119.7
C125 C126 C121 . . 120.9(4)
C125 C126 H126 . . 119.5
C121 C126 H126 . . 119.5
C136 C131 C132 . . 119.0(3)
C136 C131 P1 . . 118.8(2)
C132 C131 P1 . . 122.0(3)
C133 C132 C131 . . 119.9(3)
C133 C132 H132 . . 120.1
C131 C132 H132 . . 120.1
C134 C133 C132 . . 121.5(3)
C134 C133 H133 . . 119.2
C132 C133 H133 . . 119.2
C133 C134 C135 . . 118.5(3)
C133 C134 C137 . . 121.2(4)
C135 C134 C137 . . 120.3(4)
C136 C135 C134 . . 120.4(3)
C136 C135 H135 . . 119.8
C134 C135 H135 . . 119.8
C131 C136 C135 . . 120.6(3)
C131 C136 H136 . . 119.7
C135 C136 H136 . . 119.7
C134 C137 H13A . . 109.5
C134 C137 H13B . . 109.5
H13A C137 H13B . . 109.5
C134 C137 H13C . . 109.5
H13A C137 H13C . . 109.5
H13B C137 H13C . . 109.5
C2 O2 Cu1 . . 116.1(2)
C131 P1 C111 . . 102.98(15)
C131 P1 C121 . . 101.98(16)
C111 P1 C121 . . 105.21(17)
C131 P1 Cu1 . . 116.55(12)
C111 P1 Cu1 . . 111.62(12)
C121 P1 Cu1 . . 116.91(11)
O2 Cu1 O2 . 2_655 76.42(13)
O2 Cu1 P1 . . 112.00(7)
O2 Cu1 P1 2_655 . 108.19(7)
O2 Cu1 P1 . 2_655 108.19(7)
O2 Cu1 P1 2_655 2_655 112.00(7)
P1 Cu1 P1 . 2_655 128.18(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C2 O2 . 1.252(4)
C2 C3 . 1.426(5)
C2 C2 2_655 1.506(6)
C3 C4 . 1.387(5)
C3 Br1 . 1.911(4)
C4 C5 . 1.382(5)
C4 H4 . 0.95
C5 C4 2_655 1.382(5)
C5 Br2 . 1.893(5)
C111 C112 . 1.384(5)
C111 C116 . 1.395(5)
C111 P1 . 1.824(3)
C112 C113 . 1.400(5)
C112 H112 . 0.95
C113 C114 . 1.375(7)
C113 H113 . 0.95
C114 C115 . 1.374(7)
C114 H114 . 0.95
C115 C116 . 1.392(6)
C115 H115 . 0.95
C116 H116 . 0.95
C121 C122 . 1.381(5)
C121 C126 . 1.393(5)
C121 P1 . 1.830(4)
C122 C123 . 1.398(6)
C122 H122 . 0.95
C123 C124 . 1.396(6)
C123 H123 . 0.95
C124 C125 . 1.370(6)
C124 H124 . 0.95
C125 C126 . 1.391(6)
C125 H125 . 0.95
C126 H126 . 0.95
C131 C136 . 1.388(5)
C131 C132 . 1.403(4)
C131 P1 . 1.820(3)
C132 C133 . 1.387(5)
C132 H132 . 0.95
C133 C134 . 1.381(6)
C133 H133 . 0.95
C134 C135 . 1.405(5)
C134 C137 . 1.486(6)
C135 C136 . 1.391(5)
C135 H135 . 0.95
C136 H136 . 0.95
C137 H13A . 0.98
C137 H13B . 0.98
C137 H13C . 0.98
O2 Cu1 . 2.090(2)
P1 Cu1 . 2.2284(9)
Cu1 O2 2_655 2.090(2)
Cu1 P1 2_655 2.2284(9)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C136 H136 O2 . 0.95 2.52 3.365(4) 149
C115 H115 Cg3 3_445 0.95 2.86 3.621(4) 138.1
C137 H13A Cg2 6_566 0.98 3.18 4.144(6) 167.6
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O2 C2 C3 C4 . . 174.7(4)
C2 C2 C3 C4 2_655 . -9.2(7)
O2 C2 C3 Br1 . . -5.6(4)
C2 C2 C3 Br1 2_655 . 170.5(3)
C2 C3 C4 C5 . . -1.1(6)
Br1 C3 C4 C5 . . 179.2(2)
C3 C4 C5 C4 . 2_655 2.7(3)
C3 C4 C5 Br2 . . -177.3(3)
C116 C111 C112 C113 . . 0.9(5)
P1 C111 C112 C113 . . 176.9(3)
C111 C112 C113 C114 . . -2.6(6)
C112 C113 C114 C115 . . 2.2(6)
C113 C114 C115 C116 . . -0.1(6)
C114 C115 C116 C111 . . -1.6(6)
C112 C111 C116 C115 . . 1.2(5)
P1 C111 C116 C115 . . -174.6(3)
C126 C121 C122 C123 . . -0.4(6)
P1 C121 C122 C123 . . 177.2(4)
C121 C122 C123 C124 . . -0.2(7)
C122 C123 C124 C125 . . 0.1(8)
C123 C124 C125 C126 . . 0.4(8)
C124 C125 C126 C121 . . -1.0(8)
C122 C121 C126 C125 . . 0.9(7)
P1 C121 C126 C125 . . -176.5(4)
C136 C131 C132 C133 . . -2.1(5)
P1 C131 C132 C133 . . 173.3(3)
C131 C132 C133 C134 . . 0.8(6)
C132 C133 C134 C135 . . 1.3(6)
C132 C133 C134 C137 . . -176.7(4)
C133 C134 C135 C136 . . -2.1(5)
C137 C134 C135 C136 . . 175.8(4)
C132 C131 C136 C135 . . 1.2(5)
P1 C131 C136 C135 . . -174.3(3)
C134 C135 C136 C131 . . 0.9(5)
C3 C2 O2 Cu1 . . 171.0(2)
C2 C2 O2 Cu1 2_655 . -5.4(4)
C136 C131 P1 C111 . . -157.1(3)
C132 C131 P1 C111 . . 27.6(3)
C136 C131 P1 C121 . . 94.0(3)
C132 C131 P1 C121 . . -81.3(3)
C136 C131 P1 Cu1 . . -34.5(3)
C132 C131 P1 Cu1 . . 150.1(2)
C112 C111 P1 C131 . . 62.6(3)
C116 C111 P1 C131 . . -121.6(3)
C112 C111 P1 C121 . . 169.0(3)
C116 C111 P1 C121 . . -15.1(3)
C112 C111 P1 Cu1 . . -63.2(3)
C116 C111 P1 Cu1 . . 112.6(3)
C122 C121 P1 C131 . . -141.0(3)
C126 C121 P1 C131 . . 36.4(4)
C122 C121 P1 C111 . . 111.8(3)
C126 C121 P1 C111 . . -70.8(4)
C122 C121 P1 Cu1 . . -12.7(3)
C126 C121 P1 Cu1 . . 164.8(3)
C2 O2 Cu1 O2 . 2_655 2.14(18)
C2 O2 Cu1 P1 . . -102.3(2)
C2 O2 Cu1 P1 . 2_655 111.2(2)
C131 P1 Cu1 O2 . . 26.45(14)
C111 P1 Cu1 O2 . . 144.35(15)
C121 P1 Cu1 O2 . . -94.47(15)
C131 P1 Cu1 O2 . 2_655 -55.86(14)
C111 P1 Cu1 O2 . 2_655 62.04(15)
C121 P1 Cu1 O2 . 2_655 -176.78(14)
C131 P1 Cu1 P1 . 2_655 164.68(12)
C111 P1 Cu1 P1 . 2_655 -77.41(13)
C121 P1 Cu1 P1 . 2_655 43.76(13)
