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_4082895
_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         'C20 H36 Cu N4, F6 Sb, 2(C H2 Cl2)'
_chemical_formula_sum            'C22 H40 Cl4 Cu F6 N4 Sb'
_chemical_formula_weight         801.67
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.1220(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5180(6)
_cell_length_b                   11.3958(5)
_cell_length_c                   22.2579(10)
_cell_measurement_reflns_used    8313
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      2.34
_cell_volume                     3428.1(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0329
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            29915
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         1.747
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.771
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0569 before and 0.0419 after correction.
The Ratio of minimum to maximum transmission is 0.8776.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       prism
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.566
_refine_diff_density_min         -1.687
_refine_diff_density_rms         0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         7488
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0588
_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^)+(0.1015P)^2^+11.7640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.1723
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6178
_reflns_number_total             7488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om4012032_si_002.cif
_cod_data_source_block           dias838m_0m_a
_cod_depositor_comments          'Adding full bibliography for 4082895.cif.'
_cod_database_code               4082895
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.777
_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
 Cl2-C21 = Cl1-C21 = Cl3A-C22A = Cl3-C22 = Cl4A-C22A = Cl4-C22
 1.76 with sigma of 0.02
3. Rigid bond restraints
 Cl3A, Cl3, Cl4A, Cl4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C22A, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Cl3A \\sim Cl3 \\sim Cl4A \\sim Cl4: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
C22A \\sim C22: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C22A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.006
5. Others
 Sof(Cl3A)=Sof(Cl4A)=Sof(C22A)=Sof(H22C)=Sof(H22D)=1-FVAR(1)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(Cl3)=Sof(Cl4)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C22A(H22C,H22D)
6.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C9(H9A,
 H9B,H9C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;