Aerobic intramolecular carbon-hydrogen bond oxidation promoted by Cu(I) complexes.
Álvarez, María; Molina, Francisco; Fructos, Manuel R.; Urbano, Juan; Álvarez, Eleuterio; Sodupe, Mariona; Lledós, Agustí; Pérez, Pedro J; Dalton transactions (Cambridge, England : 2003) 49 (2020) 14647–14655; doi:10.1039/d0dt03198d

data_7705460
_publ_section_title
;
 Aerobic intramolecular carbon-hydrogen bond oxidation promoted by Cu(I)
 complexes.
;
_journal_issue                   41
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14647
_journal_page_last               14655
_journal_paper_doi               10.1039/d0dt03198d
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety
'C49 H56 B Cu N8, 1.41(C H2 Cl2), 0.29(C5 H10)'
_chemical_formula_sum            'C51.88 H61.77 B Cl2.82 Cu N8'
_chemical_formula_weight         971.80
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-14 deposited with the CCDC.	2020-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                83.494(3)
_cell_angle_beta                 88.272(3)
_cell_angle_gamma                82.151(3)
_cell_formula_units_Z            2
_cell_length_a                   11.7138(6)
_cell_length_b                   11.8974(6)
_cell_length_c                   18.4498(10)
_cell_measurement_reflns_used    9628
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.22
_cell_volume                     2530.5(2)
_computing_cell_refinement       'Bruker Apex3, 2017'
_computing_data_collection       'Bruker Apex3, 2017'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Quest'
_diffrn_measurement_device_type  'Bruker CHi Fixed D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0913
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            99549
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         2.222
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I/mS high brilliance'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.1431 before and 0.0613 after correction. 
The Ratio of minimum to maximum transmission is 0.8658. 
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       plate
_exptl_crystal_F_000             1022
_exptl_crystal_recrystallization_method
'Crystallized from a mixture of dichloromethane and petroleum ether by cooling'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.786
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     645
_refine_ls_number_reflns         9988
_refine_ls_number_restraints     140
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0399P)^2^+3.3791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1101
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7793
_reflns_number_total             9988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt03198d2.cif
_cod_data_source_block           Complex_3b
_cod_depositor_comments
'Adding full bibliography for 7705460--7705465.cif.'
_cod_database_code               7705460
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.811
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl4-C51 = Cl3-C51
 1.771 with sigma of 0.01
 Cl4-Cl3
 2.916 with sigma of 0.03
 C52-C53 \\sim C53-C54 \\sim C54-C55 \\sim C55-C56 \\sim C56-C52
 with sigma of 0.02
 C52-C54 \\sim C53-C55 \\sim C54-C56 \\sim C55-C52 \\sim C56-C53
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Cl3 \\sim Cl4 \\sim C51: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Uanis(C56) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C54) \\sim Ueq, Uanis(C55)
\\sim Ueq, Uanis(C53) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.01
4. Rigid body (RIGU) restrains
 Cl3, Cl4, C51
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C52, C53, C54, C55, C56
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(C54)=Sof(H54A)=
 Sof(H54B)=Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(C56)=Sof(H56A)=Sof(H56B)=0.5*(1-
 FVAR(2))
 Sof(Cl3)=Sof(Cl4)=Sof(C51)=Sof(H51A)=Sof(H51B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,
 H54B), C55(H55A,H55B), C56(H56A,H56B)
6.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C2(H2), C3(H3), C8(H8A), C11(H11), C14(H14), C15(H15), C20(H20),
 C23(H23), C26(H26), C27(H27), C32(H32), C35(H35), C38(H38), C39(H39), C44(H44),
  C47(H47)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C),
 C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C25(H25A,H25B,H25C), C31(H31A,H31B,
 H31C), C34(H34A,H34B,H34C), C37(H37A,H37B,H37C), C43(H43A,H43B,H43C), C46(H46A,
 H46B,H46C), C49(H49A,H49B,H49C)
;
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a 200 micro/m MITEGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'