#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/19/4321973.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_4321973
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 Cl Cu N3 O'
_chemical_formula_weight         383.38
_chemical_name_systematic        ' ?'
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_type_scat_source
'International Tables for Crystallography (Vol C)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.738(3)
_cell_length_b                   14.503(4)
_cell_length_c                   19.731(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    203
_cell_measurement_theta_max      21
_cell_measurement_theta_min      16
_cell_volume                     3358.9(14)
_computing_cell_refinement       CAD4_(Enraf-Nonius,_1977)
_computing_data_collection       CAD4_(Enraf-Nonius,_1977)
_computing_data_reduction        PROCESS_MolEN_(Fair,_1990)
_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      203
_diffrn_measurement_device_type  Enraf_Nonius_CAD4
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2553
_diffrn_reflns_theta_max         22.67
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0.87
_diffrn_standards_interval_time  83
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.470
_exptl_absorpt_correction_T_max  0.8021
_exptl_absorpt_correction_T_min  0.5681
_exptl_absorpt_correction_type   refdelf_(Walker_&_Stuart,_1983)
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.52
_exptl_crystal_description       plate
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.26
_refine_diff_density_min         -1.63
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2228
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.086
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.278
_reflns_number_gt                1668
_reflns_number_total             2228
_reflns_threshold_expression     >2.0σ(I)
_cod_data_source_file            ic981324f_4.cif
_cod_data_source_block           Cu(pamap)Cl_(JEM_11)
_cod_original_cell_volume        3359(2)
_cod_original_formula_sum        'C17 H22 Cl1 Cu1 N3 O1'
_cod_database_code               4321973
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x+1/2, y, -z+1/2'
'x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
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 0.93436(9) 0.26754(7) 0.54100(5) 0.0153(4) Uani ?
Cl 0.78811(19) 0.15643(15) 0.49057(12) 0.0277(7) Uani ?
O(19) 0.8274(5) 0.3467(4) 0.5860(3) 0.0250(17) Uani ?
N(1) 0.9428(6) 0.3603(5) 0.4647(4) 0.020(2) Uani ?
N(8) 1.0661(6) 0.2116(5) 0.4868(4) 0.019(2) Uani ?
N(12) 0.9793(6) 0.1982(4) 0.6288(3) 0.0160(18) Uani ?
C(2) 0.8971(8) 0.4454(6) 0.4625(4) 0.022(2) Uani ?
C(3) 0.9098(7) 0.5033(6) 0.4077(4) 0.022(2) Uani ?
C(4) 0.9705(8) 0.4740(6) 0.3526(4) 0.028(3) Uani ?
C(5) 1.0178(8) 0.3871(6) 0.3547(4) 0.025(2) Uani ?
C(6) 1.0033(6) 0.3319(5) 0.4106(4) 0.016(2) Uani ?
C(7) 1.0478(9) 0.2343(6) 0.4159(5) 0.026(3) Uani ?
C(9) 1.0865(8) 0.1102(6) 0.4958(4) 0.022(2) Uani ?
C(10) 1.1092(8) 0.0862(6) 0.5680(5) 0.027(2) Uani ?
C(11) 1.0107(8) 0.0995(5) 0.6149(5) 0.025(2) Uani ?
C(13) 0.8759(8) 0.1967(5) 0.6732(4) 0.021(2) Uani ?
C(14) 0.8417(7) 0.2904(6) 0.7003(4) 0.018(2) Uani ?
C(15) 0.8348(8) 0.3090(7) 0.7673(4) 0.029(3) Uani ?
C(16) 0.7980(9) 0.3940(7) 0.7918(5) 0.035(3) Uani ?
C(17) 0.7687(8) 0.4609(6) 0.7457(5) 0.029(2) Uani ?
C(18) 0.7749(7) 0.4443(6) 0.6764(5) 0.025(2) Uani ?
C(19) 0.8146(7) 0.3602(5) 0.6513(4) 0.018(2) Uani ?
C(20) 1.0729(8) 0.2461(6) 0.6623(5) 0.021(3) Uani ?
H(1) 0.8552 0.4659 0.4995 0.0290 Uiso calc
H(2) 0.8775 0.5618 0.4082 0.0280 Uiso calc
H(3) 0.9795 0.5117 0.3148 0.0360 Uiso calc
H(4) 1.0598 0.3656 0.3179 0.0330 Uiso calc
H(5) 1.1307 0.2411 0.5001 0.0240 Uiso calc
H(65) 0.8553 0.2634 0.7982 0.0380 Uiso calc
H(76) 0.7935 0.4051 0.8381 0.0450 Uiso calc
H(87) 0.7443 0.5182 0.7612 0.0370 Uiso calc
H(98) 0.7522 0.4901 0.6463 0.0330 Uiso calc
H(10) 0.9932 0.1918 0.3962 0.0340 Uiso calc
H(11) 1.1188 0.2287 0.3911 0.0340 Uiso calc
H(12) 1.0203 0.0764 0.4801 0.0280 Uiso calc
H(13) 1.1511 0.0918 0.4683 0.0280 Uiso calc
H(14A) 1.1723 0.1235 0.5840 0.0350 Uiso calc
H(15B) 1.1328 0.0222 0.5702 0.0350 Uiso calc
H(16A) 1.0283 0.0698 0.6576 0.0320 Uiso calc
H(17B) 0.9449 0.0685 0.5958 0.0320 Uiso calc
H(18A) 0.8902 0.1558 0.7112 0.0270 Uiso calc
H(19B) 0.8127 0.1713 0.6476 0.0270 Uiso calc
H(20A) 1.0483 0.3066 0.6756 0.0280 Uiso calc
H(21B) 1.1361 0.2514 0.6316 0.0280 Uiso calc
H(22C) 1.0959 0.2120 0.7017 0.0280 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) 88.8(3) ?
O(19) Cu N(8) 166.6(3) ?
N(1) Cu N(8) 80.6(3) ?
O(19) Cu N(12) 94.0(3) ?
N(1) Cu N(12) 159.0(3) ?
N(8) Cu N(12) 93.0(3) ?
O(19) Cu Cl 96.78(19) ?
N(1) Cu Cl 99.3(2) ?
N(8) Cu Cl 93.1(2) ?
N(12) Cu Cl 100.99(19) ?
C(19) O(19) Cu 128.2(5) ?
C(2) N(1) C(6) 117.7(8) ?
C(2) N(1) Cu 127.9(6) ?
C(6) N(1) Cu 114.4(6) ?
C(20) N(12) C(13) 110.6(7) ?
C(20) N(12) C(11) 110.6(7) ?
C(13) N(12) C(11) 106.9(6) ?
C(20) N(12) Cu 109.8(5) ?
C(13) N(12) Cu 106.8(5) ?
C(11) N(12) Cu 111.9(5) ?
C(7) N(8) C(9) 111.0(7) ?
C(7) N(8) Cu 107.6(5) ?
C(9) N(8) Cu 116.6(5) ?
N(1) C(2) C(3) 122.8(8) ?
C(4) C(3) C(2) 119.5(8) ?
C(3) C(4) C(5) 118.0(8) ?
C(6) C(5) C(4) 120.5(8) ?
N(1) C(6) C(5) 121.6(8) ?
N(1) C(6) C(7) 114.4(7) ?
C(5) C(6) C(7) 123.9(7) ?
N(8) C(7) C(6) 109.2(7) ?
C(10) C(9) N(8) 111.7(7) ?
C(9) C(10) C(11) 115.1(8) ?
C(10) C(11) N(12) 115.2(7) ?
N(12) C(13) C(14) 114.1(7) ?
C(15) C(14) C(19) 120.3(8) ?
C(15) C(14) C(13) 122.7(8) ?
C(19) C(14) C(13) 117.0(7) ?
C(14) C(15) C(16) 122.2(9) ?
C(17) C(16) C(15) 118.4(9) ?
C(16) C(17) C(18) 121.0(8) ?
C(17) C(18) C(19) 121.2(8) ?
O(19) C(19) C(18) 121.1(7) ?
O(19) C(19) C(14) 122.0(7) ?
C(18) C(19) C(14) 116.8(7) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu O(19) 1.919(6) ?
Cu N(1) 2.021(7) ?
Cu N(8) 2.047(7) ?
Cu N(12) 2.071(7) ?
Cu Cl 2.556(2) ?
O(19) C(19) 1.312(9) ?
N(1) C(2) 1.347(12) ?
N(1) C(6) 1.346(10) ?
N(12) C(20) 1.458(11) ?
N(12) C(13) 1.498(11) ?
N(12) C(11) 1.503(10) ?
N(8) C(7) 1.454(12) ?
N(8) C(9) 1.500(11) ?
C(2) C(3) 1.376(12) ?
C(3) C(4) 1.368(12) ?
C(4) C(5) 1.378(13) ?
C(5) C(6) 1.374(11) ?
C(6) C(7) 1.512(12) ?
C(9) C(10) 1.491(13) ?
C(10) C(11) 1.493(13) ?
C(13) C(14) 1.515(12) ?
C(14) C(15) 1.353(12) ?
C(14) C(19) 1.435(12) ?
C(15) C(16) 1.392(13) ?
C(16) C(17) 1.373(14) ?
C(17) C(18) 1.390(13) ?
C(18) C(19) 1.397(12) ?
