#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/19/4321972.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_4321972
loop_
_publ_author_name
'Hongyan Luo'
'Jem-Mau Lo'
'Phillip E. Fanwick'
'Joseph G. Stowell'
'Mark A. Green'
_publ_contact_author_address
;    Department of Medicinal Chemistry and Molecular Pharmacology
     Purdue University
     W. Lafayette
     IN 47907
     USA
;
_publ_contact_author_email       magreen@pharmacy.purdue.edu
_publ_contact_author_fax         1(765)4941414
_publ_contact_author_name        'Mark A. Green'
_publ_contact_author_phone       1(765)4941441
_publ_section_title
;
 Monoprotic Tetradentate N3O-Donor Ligands and Their Cu(II) and Ni(II)
 Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2071
_journal_page_last               2078
_journal_paper_doi               10.1021/ic981324f
_journal_volume                  38
_journal_year                    1999
_chemical_formula_sum            'C17 H22 B Cu F4 N3 O'
_chemical_formula_weight         434.73
_chemical_name_systematic        ' ?'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source
'International Tables for Crystallography (Vol C) '
_cell_angle_alpha                90.00
_cell_angle_beta                 90.582(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.158(2)
_cell_length_b                   10.714(2)
_cell_length_c                   19.085(4)
_cell_measurement_reflns_used    7878
_cell_measurement_temperature    296
_cell_measurement_theta_max      26
_cell_measurement_theta_min      4
_cell_volume                     1872.5(7)
_computing_cell_refinement       DENZO/SCALEPACK_(Otwinowski,_1996)
_computing_data_collection       Collect_(Nonius,_1998)
_computing_data_reduction        DENZO/SCALEPACK_(Otwinowski,_1996)
_computing_molecular_graphics
;
    ORTEP (Johnson, 1976)
    Xtal_GX (Hall, 1995)
    PLUTON (Spek, 1991)
;
_computing_publication_material  CIF_VAX_MolEN_(Fair,_1990)
_computing_structure_refinement  SHELX97_(Sheldrick,_1997)
_computing_structure_solution    PATTY_(DIRDIF92,_Beurskins,_1992)
_diffrn_ambient_temperature      296
_diffrn_radiation_type           MO-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.107
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7878
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         4.00
_exptl_absorpt_coefficient_mu    1.216
_exptl_absorpt_correction_T_max  0.8034
_exptl_absorpt_correction_T_min  0.6108
_exptl_absorpt_correction_type   refined_empirical_(Otwinowski_
_exptl_crystal_colour            dark_green
_exptl_crystal_density_diffrn    1.54
_exptl_crystal_description       chunk
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.61
_refine_diff_density_min         -0.59
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3659
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.080
_refine_ls_shift/su_max          0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1337P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.209
_reflns_number_gt                1949
_reflns_number_total             3659
_reflns_threshold_expression     >2.0σ(I)
_cod_data_source_file            ic981324f_3.cif
_cod_data_source_block           '[Cu(pmaap)]2(BF4)2_(RL_378)'
_cod_original_cell_volume        1872.4(12)
_cod_original_formula_sum        'C17 H22 B1 Cu1 F4 N3 O1'
_cod_database_code               4321972
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
Cu 0.13489(10) 0.02079(7) 0.05646(4) 0.0579(3) Uani ?
F(1) 0.4496(11) 0.4622(9) 0.1648(5) 0.187(4) Uani ?
F(2) 0.3079(16) 0.3153(8) 0.2048(5) 0.256(7) Uani ?
F(3) 0.3236(9) 0.4912(7) 0.2618(4) 0.149(3) Uani ?
F(4) 0.2194(13) 0.4807(9) 0.1560(5) 0.209(5) Uani ?
O(19) 0.0845(5) 0.0826(4) -0.0355(2) 0.0597(12) Uani ?
N(1) 0.2792(7) -0.1049(5) 0.0191(3) 0.0650(18) Uani ?
N(8) 0.1958(8) -0.0617(6) 0.1494(3) 0.075(2) Uani ?
N(12) 0.0788(8) 0.1818(5) 0.1051(3) 0.067(2) Uani ?
C(2) 0.3444(9) -0.1053(7) -0.0412(5) 0.074(3) Uani ?
C(3) 0.4360(10) -0.1996(8) -0.0629(6) 0.094(3) Uani ?
C(4) 0.4578(12) -0.3007(8) -0.0156(6) 0.098(4) Uani ?
C(5) 0.3908(11) -0.3003(7) 0.0439(6) 0.086(3) Uani ?
C(6) 0.2972(9) -0.2021(7) 0.0653(5) 0.075(3) Uani ?
C(7) 0.2152(11) -0.1962(6) 0.1308(4) 0.082(3) Uani ?
C(8) 0.3362(11) -0.0116(8) 0.1742(5) 0.095(3) Uani ?
C(9) 0.0818(11) -0.0514(8) 0.2042(4) 0.086(3) Uani ?
C(10) 0.0425(12) 0.0843(9) 0.2219(4) 0.091(3) Uani ?
C(11) -0.0253(10) 0.1585(7) 0.1631(4) 0.081(3) Uani ?
C(13) 0.0181(9) 0.2774(6) 0.0558(4) 0.070(2) Uani ?
C(14) 0.1101(8) 0.2973(6) -0.0047(4) 0.061(2) Uani ?
C(15) 0.1691(9) 0.4149(6) -0.0229(4) 0.073(3) Uani ?
C(16) 0.2474(10) 0.4345(8) -0.0826(4) 0.080(3) Uani ?
C(17) 0.2766(9) 0.3351(7) -0.1267(4) 0.076(3) Uani ?
C(18) 0.2230(9) 0.2167(6) -0.1109(4) 0.067(2) Uani ?
C(19) 0.1404(8) 0.1973(6) -0.0512(3) 0.057(2) Uani ?
B 0.3278(19) 0.4301(12) 0.1995(7) 0.110(5) Uani ?
H(2) 0.3283 -0.0384 -0.0713 0.0960 Uiso calc
H(3) 0.4813 -0.1971 -0.1063 0.1220 Uiso calc
H(4) 0.5194 -0.3664 -0.0273 0.1280 Uiso calc
H(5) 0.4047 -0.3675 0.0740 0.1120 Uiso calc
H(12) 0.172(6) 0.208(4) 0.136(2) 0.032(13) Uiso ?
H(15) 0.1541 0.4819 0.0072 0.0950 Uiso calc
H(16) 0.2809 0.5141 -0.0935 0.1040 Uiso calc
H(17) 0.3318 0.3473 -0.1668 0.0990 Uiso calc
H(18) 0.2427 0.1501 -0.1406 0.0870 Uiso calc
H(7A) 0.2683 -0.2391 0.1679 0.1060 Uiso calc
H(7B) 0.1208 -0.2360 0.1248 0.1060 Uiso calc
H(8A) 0.3223 0.0714 0.1919 0.1230 Uiso calc
H(8B) 0.4038 -0.0095 0.1361 0.1230 Uiso calc
H(8C) 0.3744 -0.0639 0.2109 0.1230 Uiso calc
H(9A) 0.1163 -0.0928 0.2464 0.1120 Uiso calc
H(9B) -0.0055 -0.0944 0.1881 0.1120 Uiso calc
H(10A) -0.0246 0.0838 0.2609 0.1190 Uiso calc
H(10B) 0.1306 0.1268 0.2374 0.1190 Uiso calc
H(11A) -0.1094 0.1137 0.1447 0.1050 Uiso calc
H(11B) -0.0592 0.2379 0.1812 0.1050 Uiso calc
H(13A) -0.0780 0.2509 0.0399 0.0910 Uiso calc
H(13B) 0.0069 0.3558 0.0806 0.0910 Uiso calc
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
O(19) Cu N(1) 93.4(2) ?
O(19) Cu N(12) 93.8(2) ?
N(1) Cu N(12) 153.8(3) ?
O(19) Cu N(8) 174.1(2) ?
N(1) Cu N(8) 81.1(3) ?
N(12) Cu N(8) 92.2(2) ?
O(19) Cu O(19) 79.00(19) ?
N(1) Cu O(19) 100.9(2) ?
N(12) Cu O(19) 105.2(2) ?
N(8) Cu O(19) 99.8(2) ?
C(19) O(19) Cu 114.9(3) ?
C(19) O(19) Cu 135.8(4) ?
Cu O(19) Cu 101.00(19) ?
C(2) N(1) C(6) 120.8(7) ?
C(2) N(1) Cu 128.5(5) ?
C(6) N(1) Cu 110.7(6) ?
C(8) N(8) C(9) 111.4(7) ?
C(8) N(8) C(7) 108.9(7) ?
C(9) N(8) C(7) 108.9(7) ?
C(8) N(8) Cu 110.6(5) ?
C(9) N(8) Cu 112.9(5) ?
C(7) N(8) Cu 104.0(4) ?
C(11) N(12) C(13) 110.2(6) ?
C(11) N(12) Cu 111.4(4) ?
C(13) N(12) Cu 112.9(4) ?
N(1) C(2) C(3) 123.7(8) ?
C(2) C(3) C(4) 116.7(10) ?
C(5) C(4) C(3) 119.2(9) ?
C(4) C(5) C(6) 123.2(9) ?
N(1) C(6) C(5) 116.5(9) ?
N(1) C(6) C(7) 117.1(7) ?
C(5) C(6) C(7) 126.4(8) ?
C(6) C(7) N(8) 107.9(6) ?
N(8) C(9) C(10) 113.1(7) ?
C(11) C(10) C(9) 115.6(6) ?
N(12) C(11) C(10) 112.3(8) ?
C(14) C(13) N(12) 112.7(6) ?
C(15) C(14) C(19) 116.2(7) ?
C(15) C(14) C(13) 123.4(6) ?
C(19) C(14) C(13) 120.3(6) ?
C(16) C(15) C(14) 123.0(7) ?
C(15) C(16) C(17) 119.6(7) ?
C(16) C(17) C(18) 119.9(8) ?
C(19) C(18) C(17) 120.6(7) ?
O(19) C(19) C(18) 121.5(6) ?
O(19) C(19) C(14) 117.8(6) ?
C(18) C(19) C(14) 120.7(6) ?
F(2) B F(1) 114.4(14) ?
F(2) B F(3) 113.6(11) ?
F(1) B F(3) 109.8(11) ?
F(2) B F(4) 109.0(13) ?
F(1) B F(4) 101.3(10) ?
F(3) B F(4) 107.9(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu O(19) 1.929(4) ?
Cu N(1) 2.022(6) ?
Cu N(12) 2.028(6) ?
Cu N(8) 2.053(6) ?
Cu O(19) 2.325(5) ?
F(1) B 1.348(17) ?
F(2) B 1.248(13) ?
F(3) B 1.358(14) ?
F(4) B 1.398(16) ?
O(19) C(19) 1.365(8) ?
O(19) Cu 2.325(5) ?
N(1) C(2) 1.301(10) ?
N(1) C(6) 1.374(9) ?
N(8) C(8) 1.468(10) ?
N(8) C(9) 1.489(11) ?
N(8) C(7) 1.495(9) ?
N(12) C(11) 1.488(11) ?
N(12) C(13) 1.495(8) ?
C(2) C(3) 1.379(12) ?
C(3) C(4) 1.423(12) ?
C(4) C(5) 1.297(13) ?
C(5) C(6) 1.419(12) ?
C(6) C(7) 1.466(12) ?
C(9) C(10) 1.536(12) ?
C(10) C(11) 1.505(11) ?
C(13) C(14) 1.452(11) ?
C(14) C(15) 1.416(10) ?
C(14) C(19) 1.419(9) ?
C(15) C(16) 1.369(12) ?
C(16) C(17) 1.386(12) ?
C(17) C(18) 1.393(10) ?
C(18) C(19) 1.390(10) ?
