Coordination and Ligand Substitution Chemistry of Bis(cyclooctyne)copper(I)
Das, Animesh; Dash, Chandrakanta; Yousufuddin, Muhammed; Dias, H. V. Rasika; Organometallics 33 (2014) 1644–; doi:10.1021/om4012032

data_4082894
_publ_section_title
;
 Coordination and Ligand Substitution Chemistry of
 Bis(cyclooctyne)copper(I)
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              1644
_journal_paper_doi               10.1021/om4012032
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C18 H30 Cu N2, 1(F6 Sb)'
_chemical_formula_sum            'C18 H30 Cu F6 N2 Sb'
_chemical_formula_weight         573.73
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-12-14
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.146(5)
_cell_length_b                   7.8797(16)
_cell_length_c                   12.974(3)
_cell_measurement_reflns_used    4582
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      2.36
_cell_volume                     2366.2(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14630
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.440
_diffrn_reflns_theta_min         1.760
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.092
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0551 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.8536.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_description       platy
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.125
_refine_diff_density_min         -0.973
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.248
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         2596
_refine_ls_number_restraints     451
_refine_ls_restrained_S_all      1.187
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0554
_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/[\s^2^(Fo^2^)+(0.0263P)^2^+18.1198P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2340
_reflns_number_total             2596
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om4012032_si_002.cif
_cod_data_source_block           dias842m_0ma_a
_cod_depositor_comments          'Adding full bibliography for 4082894.cif.'
_cod_original_cell_volume        2366.3(8)
_cod_database_code               4082894
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Sb1-F2 \\sim Sb1-F1 \\sim Sb1-F3 \\sim Sb1-F4 \\sim Sb1-F5 \\sim Sb1-F6
 with sigma of 0.005
 F1-F2 \\sim F1-F3 \\sim F1-F5 \\sim F1-F6 \\sim F2-F3 \\sim F2-F4 \\sim F2-F6
\\sim F3-F4 \\sim F3-F5 \\sim F4-F5
 \\sim F4-F6 \\sim F5-F6
 with sigma of 0.005
 Sb2-F1' \\sim Sb2-F2' \\sim Sb2-F3' \\sim Sb2-F4' \\sim Sb2-F5' \\sim Sb2-F6'
 with sigma of 0.005
 F1'-F2' \\sim F1'-F3' \\sim F1'-F5' \\sim F1'-F6' \\sim F2'-F3' \\sim F2'-F4'
\\sim F2'-F6' \\sim F3'-F4'
 \\sim F3'-F5' \\sim F4'-F5' \\sim F4'-F6' \\sim F5'-F6'
 with sigma of 0.005
 Sb3-F1" \\sim Sb3-F2" \\sim Sb3-F3" \\sim Sb3-F4" \\sim Sb3-F5" \\sim Sb3-F6"
 with sigma of 0.005
 F1"-F2" \\sim F1"-F3" \\sim F1"-F5" \\sim F1"-F6" \\sim F2"-F3" \\sim F2"-F4"
\\sim F2"-F6" \\sim F3"-F4"
 \\sim F3"-F5" \\sim F4"-F5" \\sim F4"-F6" \\sim F5"-F6"
 with sigma of 0.005
 C4-C3 \\sim C5-C4 \\sim C6-C5 \\sim C7-C6 \\sim C8-C7
 with sigma of 0.01
3. Rigid bond restraints
 C3, C4, C5, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(Sb1) = Uanis(Sb2) = Uanis(Sb3)
5. Rigid body (RIGU) restrains
 F1, F2, F3, F4, F5, F6, F1', F2', F3', F4', F5', F6', F1", F2", F3", F4", F5",
  F6", Sb1, Sb2, Sb3, C7, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 1*[Sof(Sb1)+Sof(F1)+Sof(F2)+Sof(F3)+Sof(F4)+Sof(F5)+Sof(F6)]+1*[Sof(Sb2)+
 Sof(F1')+Sof(F2')+Sof(F3')+Sof(F4')+Sof(F5')+Sof(F6')]+1*[Sof(Sb3)+Sof(F1")+
 Sof(F2")+Sof(F3")+Sof(F4")+Sof(F5")+Sof(F6")]=1 with esd of 0.0001
 Sof(Sb1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=0.5*FVAR(2)
 Sof(Sb2)=Sof(F1')=Sof(F2')=Sof(F3')=Sof(F4')=Sof(F5')=Sof(F6')=0.5*FVAR(3)
 Sof(Sb3)=Sof(F1")=Sof(F2")=Sof(F3")=Sof(F4")=Sof(F5")=Sof(F6")=0.5*FVAR(4)
 Fixed Sof: C3(0.5) H3A(0.5) H3B(0.5) C4(0.5) H4A(0.5) H4B(0.5) C5(0.5)
 H5A(0.5) H5B(0.5) C6(0.5) H6A(0.5) H6B(0.5) C7(0.5) H7A(0.5) H7B(0.5) C8(0.5)
 H8A(0.5) H8B(0.5) H12A(0.5) H12B(0.5) H12C(0.5) H16A(0.5) H16B(0.5) H16C(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
7.b Me refined with riding coordinates:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C)
7.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              62703
_shelx_hkl_checksum              65437