#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:34:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180227 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/13/7111358.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7111358
loop_
_publ_author_name
'Fielden, John'
'Long, De-Liang'
'Cronin, Leroy'
_publ_section_title
;
 Secondary coordination sphere controlled reversible geometry
 reorganisations in copper(ii) complexes
;
_journal_issue                   19
_journal_name_full               'Chemical Communications'
_journal_page_first              2156
_journal_page_last               2157
_journal_paper_doi               10.1039/b407229d
_journal_year                    2004
_chemical_formula_moiety
'(C12 H28 Cu1 F N4 O2 +), (F -), 2(C H4 O), (H2 O)'
_chemical_formula_sum            'C14 H38 Cu F2 N4 O5'
_chemical_formula_weight         444.02
_chemical_name_systematic
;
?
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.4970(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2410(2)
_cell_length_b                   7.03400(10)
_cell_length_c                   14.9794(2)
_cell_measurement_reflns_used    6359
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      1.6
_cell_volume                     1003.98(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 19'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12637
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.92
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    1.137
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst.
(1965), 18, 1035-1038
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             474
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.28
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(8)
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0210
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0195P)²+0.4723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0516
_refine_ls_wR_factor_ref         0.0525
_reflns_number_gt                3506
_reflns_number_total             3615
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b407229dsup1.cif
_cod_data_source_block           jf243x_syn
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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 
;
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7111358
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu Cu 0.079695(14) 0.03841(2) 0.332780(13) 0.01179(4) Uani 1 1 d .
F1 F 0.07955(11) 0.08748(16) 0.48417(7) 0.0277(2) Uani 1 1 d .
F2 F 0.07992(10) 0.54550(12) 0.23757(7) 0.0235(2) Uani 1 1 d .
N1 N 0.22461(13) 0.2463(2) 0.35792(10) 0.0155(3) Uani 1 1 d .
H1A H 0.1849 0.3398 0.3133 0.019 Uiso 1 1 calc R
H1B H 0.2355 0.2972 0.4168 0.019 Uiso 1 1 calc R
N2 N 0.22743(14) -0.1696(2) 0.37205(10) 0.0177(4) Uani 1 1 d .
H2A H 0.2374 -0.2051 0.4333 0.021 Uiso 1 1 calc R
H2B H 0.1892 -0.2722 0.3332 0.021 Uiso 1 1 calc R
N3 N -0.06897(14) 0.2438(2) 0.28290(10) 0.0170(3) Uani 1 1 d .
H3A H -0.0796 0.2972 0.3359 0.020 Uiso 1 1 calc R
H3B H -0.0308 0.3365 0.2566 0.020 Uiso 1 1 calc R
N4 N -0.06581(14) -0.1721(2) 0.30050(11) 0.0185(4) Uani 1 1 d .
H4A H -0.0264 -0.2754 0.2823 0.022 Uiso 1 1 calc R
H4B H -0.0757 -0.2050 0.3571 0.022 Uiso 1 1 calc R
O3 O 0.32018(15) -0.0010(2) 0.11785(11) 0.0384(4) Uani 1 1 d .
H3 H 0.2854 -0.1028 0.0898 0.058 Uiso 1 1 calc R
O4 O -0.16240(15) -0.0106(2) -0.00226(11) 0.0365(4) Uani 1 1 d .
H4 H -0.1254 -0.1112 -0.0119 0.055 Uiso 1 1 calc R
C11 C 0.36894(15) 0.2143(2) 0.35824(11) 0.0169(3) Uani 1 1 d .
H11 H 0.4269 0.3285 0.3877 0.020 Uiso 1 1 calc R
C12 C 0.43654(19) 0.0428(2) 0.41915(14) 0.0192(5) Uani 1 1 d .
H12A H 0.4257 0.0534 0.4820 0.023 Uiso 1 1 calc R
H12B H 0.5382 0.0428 0.4311 0.023 Uiso 1 1 calc R
C13 C 0.37301(16) -0.1452(2) 0.37220(12) 0.0193(4) Uani 1 1 d .
H13 H 0.4325 -0.2508 0.4108 0.023 Uiso 1 1 calc R
C14 C 0.37222(17) -0.1587(2) 0.27046(13) 0.0234(4) Uani 1 1 d .
H14A H 0.3236 -0.2772 0.2405 0.028 Uiso 1 1 calc R
H14B H 0.4703 -0.1671 0.2736 0.028 Uiso 1 1 calc R
C15 C 0.30075(19) 0.0093(3) 0.20709(13) 0.0230(4) Uani 1 1 d .
H15 H 0.1982 0.0078 0.1954 0.028 Uiso 1 1 calc R
C16 C 0.36494(17) 0.1950(2) 0.25547(12) 0.0204(4) Uani 1 1 d .
H16A H 0.3103 0.3022 0.2168 0.024 Uiso 1 1 calc R
H16B H 0.4619 0.2048 0.2564 0.024 Uiso 1 1 calc R
C21 C -0.21287(16) 0.2074(2) 0.21239(11) 0.0179(4) Uani 1 1 d .
H21 H -0.2723 0.3203 0.2124 0.021 Uiso 1 1 calc R
C22 C -0.2775(2) 0.0339(3) 0.24120(14) 0.0187(5) Uani 1 1 d .
H22A H -0.3792 0.0303 0.2023 0.022 Uiso 1 1 calc R
H22B H -0.2666 0.0460 0.3094 0.022 Uiso 1 1 calc R
C23 C -0.21066(16) -0.1522(2) 0.22750(12) 0.0190(4) Uani 1 1 d .
H23 H -0.2686 -0.2592 0.2370 0.023 Uiso 1 1 calc R
C24 C -0.20923(18) -0.1681(2) 0.12686(13) 0.0225(4) Uani 1 1 d .
H24A H -0.3069 -0.1826 0.0810 0.027 Uiso 1 1 calc R
H24B H -0.1571 -0.2843 0.1229 0.027 Uiso 1 1 calc R
C25 C -0.14262(19) 0.0027(3) 0.09664(13) 0.0225(4) Uani 1 1 d .
H25 H -0.0399 0.0060 0.1359 0.027 Uiso 1 1 calc R
C26 C -0.21029(18) 0.1863(2) 0.11171(12) 0.0214(4) Uani 1 1 d .
H26A H -0.3078 0.1918 0.0646 0.026 Uiso 1 1 calc R
H26B H -0.1585 0.2952 0.0988 0.026 Uiso 1 1 calc R
O1 O 0.31196(15) 0.5210(2) 0.52196(10) 0.0313(3) Uani 1 1 d .
H1F H 0.2533 0.5050 0.5484 0.047 Uiso 1 1 calc R
C1 C 0.4486(2) 0.4874(3) 0.58927(16) 0.0392(5) Uani 1 1 d .
H1C H 0.5152 0.4838 0.5561 0.059 Uiso 1 1 calc R
H1D H 0.4506 0.3655 0.6214 0.059 Uiso 1 1 calc R
H1E H 0.4749 0.5897 0.6370 0.059 Uiso 1 1 calc R
O2 O -0.15232(14) 0.52172(19) 0.40620(10) 0.0295(3) Uani 1 1 d .
H2F H -0.0940 0.5062 0.4622 0.044 Uiso 1 1 calc R
C2 C -0.2894(2) 0.4882(3) 0.40452(15) 0.0350(5) Uani 1 1 d .
H2C H -0.3116 0.5816 0.4454 0.053 Uiso 1 1 calc R
H2D H -0.2946 0.3598 0.4284 0.053 Uiso 1 1 calc R
H2E H -0.3570 0.5000 0.3386 0.053 Uiso 1 1 calc R
O O 0.08011(14) 0.43017(19) 0.56463(10) 0.0295(3) Uani 1 1 d D
H1 H 0.077(2) 0.443(3) 0.6185(10) 0.044 Uiso 1 1 d D
H2 H 0.073(2) 0.317(2) 0.5501(14) 0.044 Uiso 1 1 d D
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 Cu N4 177.00(7)
N1 Cu N2 92.81(6)
N4 Cu N2 86.98(5)
N1 Cu N3 87.38(5)
N4 Cu N3 92.60(6)
N2 Cu N3 175.58(6)
N1 Cu F1 88.48(5)
N4 Cu F1 94.53(5)
N2 Cu F1 95.30(5)
N3 Cu F1 89.12(5)
C11 N1 Cu 123.43(10)
C13 N2 Cu 123.55(11)
C21 N3 Cu 123.56(11)
C23 N4 Cu 123.51(11)
N1 C11 C12 110.76(14)
N1 C11 C16 110.39(12)
C12 C11 C16 111.85(14)
C11 C12 C13 112.82(14)
N2 C13 C14 110.50(13)
N2 C13 C12 110.82(14)
C14 C13 C12 111.09(15)
C13 C14 C15 113.57(14)
O3 C15 C16 107.83(15)
O3 C15 C14 110.18(15)
C16 C15 C14 110.11(14)
C15 C16 C11 113.75(14)
N3 C21 C22 110.90(14)
N3 C21 C26 110.32(14)
C22 C21 C26 111.64(14)
C21 C22 C23 112.70(17)
N4 C23 C24 110.62(14)
N4 C23 C22 110.89(14)
C24 C23 C22 111.42(14)
C23 C24 C25 113.82(14)
O4 C25 C26 108.15(15)
O4 C25 C24 110.34(15)
C26 C25 C24 110.26(15)
C25 C26 C21 113.77(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cu N1 2.0180(14)
Cu N4 2.0295(15)
Cu N2 2.0306(14)
Cu N3 2.0320(14)
Cu F1 2.2944(10)
N1 C11 1.493(2)
N2 C13 1.500(2)
N3 C21 1.4872(19)
N4 C23 1.492(2)
O3 C15 1.424(2)
O4 C25 1.423(2)
C11 C12 1.518(2)
C11 C16 1.531(2)
C12 C13 1.527(2)
C13 C14 1.524(2)
C14 C15 1.524(3)
C15 C16 1.522(2)
C21 C22 1.525(3)
C21 C26 1.525(2)
C22 C23 1.526(3)
C23 C24 1.517(2)
C24 C25 1.530(3)
C25 C26 1.521(2)
O1 C1 1.413(3)
O2 C2 1.415(3)
