#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:37:02 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179338 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/35/4323584.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_4323584
loop_
_publ_author_name
'Nydia D. Villanueva'
'Jeffrey R. Bocarsly'
'Joseph W. Ziller'
_publ_section_title
;
 A Trapped Intermediate in the Copper(II)-Mediated Template Synthesis of
 an Amino Acid-Containing Ligand
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4585
_journal_page_last               4592
_journal_paper_doi               10.1021/ic961409l
_journal_volume                  36
_journal_year                    1997
_chemical_formula_sum            'C13 H18 Cl Cu N2 O7'
_chemical_formula_weight         413.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0066(5)
_cell_length_b                   11.1040(6)
_cell_length_c                   16.0091(15)
_cell_measurement_reflns_used    42
_cell_measurement_temperature    163
_cell_measurement_theta_max      14.30
_cell_measurement_theta_min      5.05
_cell_volume                     1601.06(19)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        CARESS
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      163
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2θ/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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1630
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        '< 1.0%'
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.570
_exptl_absorpt_correction_T_max  0.5764
_exptl_absorpt_correction_T_min  0.5332
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    n/a
_exptl_crystal_description       Prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.054
_refine_ls_goodness_of_fit_obs   1.080
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         1630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_restrained_S_obs      1.080
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_obs          0.0265
_refine_ls_shift/esd_max         0.017
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0326P)²+1.1255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0637
_refine_ls_wR_factor_obs         0.0612
_reflns_number_observed          1471
_reflns_number_total             1630
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic961409l.cif
_cod_data_source_block           jrb1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+1.1255P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+1.1255P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1601.1(2)
_cod_database_code               4323584
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'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Cu1 Cu -0.05869(6) 0.69304(4) 0.45194(3) 0.0265(2) Uani 1 d . .
N1 N -0.1270(4) 0.5214(3) 0.4551(2) 0.0218(7) Uani 1 d . .
N2 N 0.0846(4) 0.6322(4) 0.3674(3) 0.0302(9) Uani 1 d . .
O1 O -0.2496(3) 0.7299(2) 0.5047(2) 0.0281(7) Uani 1 d . .
O2 O -0.4737(3) 0.6508(2) 0.5253(2) 0.0317(8) Uani 1 d . .
O3 O -0.1976(4) 0.6953(4) 0.3259(2) 0.0492(9) Uani 1 d . .
C1 C -0.2879(4) 0.5188(4) 0.4754(3) 0.0210(9) Uani 1 d . .
C2 C -0.3384(5) 0.6436(4) 0.5040(3) 0.0243(9) Uani 1 d . .
C3 C -0.0764(6) 0.4592(4) 0.3777(3) 0.0288(10) Uani 1 d . .
C4 C -0.0049(5) 0.5466(4) 0.3157(3) 0.0318(10) Uani 1 d . .
C5 C -0.1216(6) 0.6214(5) 0.2694(3) 0.0412(13) Uani 1 d . .
C6 C 0.0903(8) 0.4774(6) 0.2530(4) 0.049(2) Uani 1 d . .
C7 C -0.3269(5) 0.4234(4) 0.5403(3) 0.0265(9) Uani 1 d . .
C8 C -0.2964(4) 0.2935(4) 0.5145(3) 0.0264(9) Uani 1 d . .
C9 C -0.2185(5) 0.2177(4) 0.5657(3) 0.0323(11) Uani 1 d . .
C10 C -0.1961(5) 0.0976(4) 0.5439(4) 0.0427(12) Uani 1 d . .
C11 C -0.2527(6) 0.0544(5) 0.4706(4) 0.0428(15) Uani 1 d . .
C12 C -0.3310(6) 0.1298(5) 0.4176(4) 0.0391(12) Uani 1 d . .
C13 C -0.3512(5) 0.2492(4) 0.4394(3) 0.0310(11) Uani 1 d . .
O4 O 0.5194(6) 0.3865(4) 0.1253(2) 0.079(2) Uani 1 d . .
O5 O 0.7184(5) 0.3309(5) 0.2106(3) 0.0786(15) Uani 1 d . .
O6 O 0.4909(12) 0.2419(10) 0.2305(8) 0.103(4) Uani 0.70 d P .
O6A O 0.5468(36) 0.2121(29) 0.1700(17) 0.150(12) Uani 0.30 d P .
O7 O 0.5291(13) 0.4399(10) 0.2671(6) 0.094(4) Uani 0.70 d P .
O7A O 0.4692(33) 0.3509(40) 0.2574(13) 0.140(14) Uani 0.30 d P .
Cl1 Cl 0.5643(2) 0.34608(13) 0.20472(8) 0.0505(4) Uani 1 d . .
H1 H -0.0821(52) 0.4887(38) 0.4942(28) 0.024(12) Uiso 1 d . .
H3 H -0.2969(57) 0.7397(44) 0.3068(29) 0.040 Uiso 1 d . .
H1A H -0.3327(47) 0.5021(37) 0.4237(27) 0.019(11) Uiso 1 d . .
H2A H 0.1235(67) 0.6761(62) 0.3335(38) 0.061(21) Uiso 1 d . .
H2B H 0.1558(54) 0.5976(43) 0.3907(27) 0.024(13) Uiso 1 d . .
H3A H -0.0080(48) 0.4018(41) 0.3948(26) 0.025(12) Uiso 1 d . .
H3B H -0.1549(54) 0.4306(42) 0.3521(29) 0.030(13) Uiso 1 d . .
H5A H -0.0733(63) 0.6758(47) 0.2337(31) 0.045(14) Uiso 1 d . .
H5B H -0.1924(66) 0.5602(52) 0.2373(33) 0.058(17) Uiso 1 d . .
H6A H 0.1864(53) 0.4349(38) 0.2755(25) 0.020(11) Uiso 1 d . .
H6B H 0.0269(72) 0.4324(58) 0.2231(36) 0.064(20) Uiso 1 d . .
H6C H 0.1287(72) 0.5176(57) 0.2155(41) 0.067(22) Uiso 1 d . .
H7A H -0.4253(55) 0.4363(39) 0.5559(27) 0.032(12) Uiso 1 d . .
H7B H -0.2683(53) 0.4364(42) 0.5851(28) 0.029(13) Uiso 1 d . .
H9 H -0.1747(60) 0.2424(47) 0.6155(31) 0.048(16) Uiso 1 d . .
H10 H -0.1457(55) 0.0465(48) 0.5839(31) 0.044(15) Uiso 1 d . .
H11 H -0.2466(70) -0.0187(56) 0.4567(38) 0.067(19) Uiso 1 d . .
H12 H -0.3700(53) 0.0990(47) 0.3743(31) 0.038(15) Uiso 1 d . .
H13 H -0.4111(56) 0.2958(47) 0.4070(28) 0.036(13) Uiso 1 d . .
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'
O O 0.0106 0.0060 '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'
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
_geom_angle_publ_flag
O2 Cu1 O1 94.54(12) 4_566 . yes
O2 Cu1 N2 100.16(15) 4_566 . yes
O1 Cu1 N2 159.10(14) . . yes
O2 Cu1 N1 166.33(15) 4_566 . yes
O1 Cu1 N1 85.31(12) . . yes
N2 Cu1 N1 83.9(2) . . yes
O2 Cu1 O3 111.11(14) 4_566 . yes
O1 Cu1 O3 84.36(13) . . yes
N2 Cu1 O3 76.5(2) . . yes
N1 Cu1 O3 82.51(15) . . yes
C1 N1 C3 118.2(3) . . yes
C1 N1 Cu1 108.8(2) . . yes
C3 N1 Cu1 109.0(3) . . yes
C4 N2 Cu1 104.0(3) . . yes
C2 O1 Cu1 113.5(2) . . yes
C2 O2 Cu1 119.3(3) . 4_466 yes
C5 O3 Cu1 106.6(3) . . yes
N1 C1 C7 112.8(4) . . yes
N1 C1 C2 109.8(3) . . yes
C7 C1 C2 110.9(3) . . yes
O1 C2 O2 124.4(4) . . yes
O1 C2 C1 120.6(4) . . yes
O2 C2 C1 115.1(4) . . yes
N1 C3 C4 112.0(3) . . yes
N2 C4 C5 107.1(4) . . yes
N2 C4 C6 112.4(4) . . yes
C5 C4 C6 109.9(4) . . yes
N2 C4 C3 105.7(4) . . yes
C5 C4 C3 111.7(4) . . yes
C6 C4 C3 110.1(4) . . yes
O3 C5 C4 109.9(4) . . yes
C1 C7 C8 115.6(4) . . yes
C9 C8 C13 118.9(4) . . yes
C9 C8 C7 120.8(4) . . yes
C13 C8 C7 120.3(4) . . yes
C8 C9 C10 120.9(5) . . yes
C11 C10 C9 119.8(5) . . yes
C10 C11 C12 120.2(5) . . yes
C11 C12 C13 119.5(5) . . yes
C12 C13 C8 120.7(5) . . yes
O6A O6 O7A 128.2(21) . . no
O6A O6 Cl1 77.3(16) . . no
O7A O6 Cl1 52.9(11) . . no
O6 O6A Cl1 58.5(16) . . no
O7A O7 Cl1 52.9(11) . . no
O7 O7A Cl1 78.3(22) . . no
O7 O7A O6 141.6(25) . . no
Cl1 O7A O6 67.6(15) . . no
O7A Cl1 O6 59.5(19) . . no
O7A Cl1 O5 131.5(13) . . no
O6 Cl1 O5 110.5(5) . . no
O7A Cl1 O4 114.5(11) . . no
O6 Cl1 O4 113.3(5) . . no
O5 Cl1 O4 112.6(3) . . no
O7A Cl1 O7 48.9(22) . . no
O6 Cl1 O7 106.5(8) . . no
O5 Cl1 O7 104.6(5) . . no
O4 Cl1 O7 108.9(5) . . no
O7A Cl1 O6A 102.4(23) . . no
O6 Cl1 O6A 44.2(8) . . no
O5 Cl1 O6A 90.5(12) . . no
O4 Cl1 O6A 87.4(10) . . no
O7 Cl1 O6A 150.6(11) . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.930(3) 4_566 yes
Cu1 O1 1.959(3) . yes
Cu1 N2 1.989(4) . yes
Cu1 N1 2.004(3) . yes
Cu1 O3 2.374(4) . yes
N1 C1 1.486(5) . yes
N1 C3 1.489(5) . yes
N2 C4 1.496(6) . yes
O1 C2 1.247(5) . yes
O2 C2 1.268(5) . yes
O2 Cu1 1.930(3) 4_466 no
O3 C5 1.401(6) . yes
C1 C7 1.525(6) . yes
C1 C2 1.529(5) . yes
C3 C4 1.530(6) . yes
C4 C5 1.531(7) . yes
C4 C6 1.527(7) . yes
C7 C8 1.526(6) . yes
C8 C9 1.368(6) . yes
C8 C13 1.390(6) . yes
C9 C10 1.393(7) . yes
C10 C11 1.367(8) . yes
C11 C12 1.384(8) . yes
C12 C13 1.383(7) . yes
O4 Cl1 1.408(4) . no
O5 Cl1 1.401(4) . no
O6 O6A 1.14(3) . no
O6 O7A 1.30(4) . no
O6 Cl1 1.394(8) . no
O6A Cl1 1.60(3) . no
O7 O7A 1.14(4) . no
O7 Cl1 1.478(8) . no
O7A Cl1 1.20(2) . no
