#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:41:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178663 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/74/4077487.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_4077487
loop_
_publ_author_name
'Gröger, Gunther'
'Behrens, Ulrich'
'Olbrich, Falk'
_publ_section_title
;
 Monomeric and Dimeric Cyclooctyne-Stabilized Complexes of Copper(I)1
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              3354
_journal_paper_doi               10.1021/om000079g
_journal_volume                  19
_journal_year                    2000
_chemical_formula_sum            'C16 H24 Cu I'
_chemical_formula_weight         406.79
_chemical_name_common            '[CuI(coct)2]'
_chemical_name_systematic
; 
 bis(cyclooctyne)iodo-copper  
;
_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_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.1090(1)
_cell_length_b                   9.3298(1)
_cell_length_c                   22.6794(2)
_cell_measurement_temperature    173(2)
_cell_volume                     3196.98(5)
_computing_cell_refinement       'Siemens axs SAINT'
_computing_data_collection       'Siemens axs SMART'
_computing_data_reduction        'Siemens axs SAINT'
_computing_molecular_graphics    'SHELXTL PLUS (Siemens, 1992)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.893
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_device_type  'Siemens axs SMART CCD System'
_diffrn_measurement_method       omega-scan
_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  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20348
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    3.280
_exptl_absorpt_correction_T_max  0.5599
_exptl_absorpt_correction_T_min  0.2908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'program SADABS (Siemens axs System)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.303
_refine_diff_density_min         -1.276
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       0.00350(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0404P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0723
_reflns_number_gt                3239
_reflns_number_total             3967
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om000079g.cif
_cod_data_source_block           CuI(coct)2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not determined' 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^)+(0.0404P)^2^+0.0000P] 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^)+(0.0404P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4077487
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_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_calc_flag
_atom_site_refinement_flags
I1 I 0.069074(11) 0.81175(2) 0.357895(8) 0.02956(8) Uani 1 d .
Cu1 Cu 0.230588(19) 0.86374(3) 0.336532(14) 0.02213(9) Uani 1 d .
C2 C 0.34428(17) 0.8158(3) 0.38539(12) 0.0248(5) Uani 1 d .
C1 C 0.28159(17) 0.7549(3) 0.40825(12) 0.0266(6) Uani 1 d .
C8 C 0.23743(19) 0.6669(3) 0.45332(13) 0.0324(6) Uani 1 d .
H8B H 0.1961 0.5989 0.4342 0.0406(18) Uiso 1 calc R
H8A H 0.2030 0.7290 0.4802 0.0406(18) Uiso 1 calc R
C7 C 0.30775(19) 0.5836(3) 0.48845(13) 0.0363(7) Uani 1 d .
H7B H 0.2784 0.5376 0.5226 0.0406(18) Uiso 1 calc R
H7A H 0.3313 0.5062 0.4630 0.0406(18) Uiso 1 calc R
C6 C 0.3856(2) 0.6720(3) 0.51124(13) 0.0386(7) Uani 1 d .
H6B H 0.4059 0.6281 0.5486 0.0406(18) Uiso 1 calc R
H6A H 0.3632 0.7689 0.5209 0.0406(18) Uiso 1 calc R
C5 C 0.4669(2) 0.6897(3) 0.47072(14) 0.0375(7) Uani 1 d .
H5B H 0.5204 0.6658 0.4940 0.0406(18) Uiso 1 calc R
H5A H 0.4623 0.6180 0.4387 0.0406(18) Uiso 1 calc R
C4 C 0.4813(2) 0.8366(3) 0.44257(14) 0.0370(7) Uani 1 d .
H4B H 0.5458 0.8520 0.4381 0.0406(18) Uiso 1 calc R
H4A H 0.4590 0.9104 0.4702 0.0406(18) Uiso 1 calc R
C3 C 0.43776(16) 0.8614(3) 0.38261(13) 0.0291(6) Uani 1 d .
H3B H 0.4412 0.9643 0.3721 0.0406(18) Uiso 1 calc R
H3A H 0.4693 0.8058 0.3519 0.0406(18) Uiso 1 calc R
C12 C 0.29254(16) 0.9707(3) 0.26675(11) 0.0246(5) Uani 1 d .
C11 C 0.21279(17) 0.9835(3) 0.26106(12) 0.0264(6) Uani 1 d .
C18 C 0.13201(18) 1.0296(3) 0.23001(13) 0.0334(6) Uani 1 d .
H18B H 0.1101 1.1205 0.2472 0.0406(18) Uiso 1 calc R
H18A H 0.0852 0.9561 0.2345 0.0406(18) Uiso 1 calc R
C17 C 0.15324(18) 1.0509(3) 0.16454(13) 0.0356(7) Uani 1 d .
H17B H 0.1003 1.0911 0.1449 0.0406(18) Uiso 1 calc R
H17A H 0.1650 0.9559 0.1467 0.0406(18) Uiso 1 calc R
C16 C 0.2325(2) 1.1495(3) 0.15151(14) 0.0346(7) Uani 1 d .
H16B H 0.2351 1.2230 0.1830 0.0406(18) Uiso 1 calc R
H16A H 0.2203 1.2002 0.1140 0.0406(18) Uiso 1 calc R
C15 C 0.32532(19) 1.0806(3) 0.14657(11) 0.0302(6) Uani 1 d .
H15B H 0.3174 0.9763 0.1407 0.0406(18) Uiso 1 calc R
H15A H 0.3541 1.1187 0.1106 0.0406(18) Uiso 1 calc R
C14 C 0.38898(17) 1.1021(3) 0.19827(12) 0.0287(6) Uani 1 d .
H14B H 0.3769 1.1970 0.2161 0.0406(18) Uiso 1 calc R
H14A H 0.4501 1.1045 0.1826 0.0406(18) Uiso 1 calc R
C13 C 0.38484(16) 0.9881(3) 0.24758(12) 0.0283(6) Uani 1 d .
H13B H 0.4080 0.8956 0.2327 0.0406(18) Uiso 1 calc R
H13A H 0.4219 1.0185 0.2813 0.0406(18) Uiso 1 calc R
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C11 Cu1 C1 165.55(10)
C11 Cu1 C12 34.08(10)
C1 Cu1 C12 131.52(10)
C11 Cu1 C2 131.48(10)
C1 Cu1 C2 34.11(10)
C12 Cu1 C2 97.77(10)
C11 Cu1 I1 97.87(7)
C1 Cu1 I1 96.58(7)
C12 Cu1 I1 131.81(7)
C2 Cu1 I1 130.41(8)
C1 C2 C3 153.5(3)
C1 C2 Cu1 71.77(17)
C3 C2 Cu1 134.5(2)
C2 C1 C8 155.1(3)
C2 C1 Cu1 74.11(17)
C8 C1 Cu1 130.69(19)
C1 C8 C7 109.2(2)
C6 C7 C8 115.8(3)
C7 C6 C5 118.0(3)
C4 C5 C6 117.2(3)
C5 C4 C3 116.5(2)
C2 C3 C4 109.3(2)
C11 C12 C13 153.7(3)
C11 C12 Cu1 71.61(16)
C13 C12 Cu1 134.50(18)
C12 C11 C18 154.0(3)
C12 C11 Cu1 74.31(17)
C18 C11 Cu1 131.53(19)
C11 C18 C17 109.1(2)
C18 C17 C16 115.2(2)
C17 C16 C15 118.1(2)
C14 C15 C16 117.4(2)
C15 C14 C13 116.0(2)
C12 C13 C14 109.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 Cu1 2.5348(3)
Cu1 C11 2.062(3)
Cu1 C1 2.066(3)
Cu1 C12 2.092(2)
Cu1 C2 2.092(2)
C2 C1 1.220(4)
C2 C3 1.476(4)
C1 C8 1.472(4)
C8 C7 1.538(4)
C7 C6 1.526(4)
C6 C5 1.544(4)
C5 C4 1.528(4)
C4 C3 1.528(4)
C12 C11 1.218(4)
C12 C13 1.470(3)
C11 C18 1.473(4)
C18 C17 1.532(4)
C17 C16 1.539(4)
C16 C15 1.546(4)
C15 C14 1.530(4)
C14 C13 1.545(3)
