C(sp<sup>3</sup>)-H cyanation by a formal copper(iii) cyanide complex.
Bower, Jamey K.; Reese, Maxwell S.; Mazin, Ilia M.; Zarnitsa, Lina M.; Cypcar, Andrew D.; Moore, Curtis E.; Sokolov, Alexander Yu; Zhang, Shiyu; Chemical science 14 (2023) 1301–1307; doi:10.1039/d2sc06573h

data_1568276
_publ_section_title
;
 C(sp<sup>3</sup>)-H cyanation by a formal copper(iii) cyanide complex.
;
_journal_issue                   5
_journal_name_full               'Chemical science'
_journal_page_first              1301
_journal_page_last               1307
_journal_paper_doi               10.1039/d2sc06573h
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C32 H37 Cu N4 O2, C16 H36 N, 2(C4 H8 O)'
_chemical_formula_sum            'C56 H89 Cu N5 O4'
_chemical_formula_weight         959.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2b9f8c
_audit_creation_date             2022-02-17
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2021.12.21 svn.raa29eb21 for OlexSys, GUI svn.r6440)
;
_audit_update_record
;
2022-02-22 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.477(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2900(6)
_cell_length_b                   26.6421(15)
_cell_length_c                   20.4572(12)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      23.375
_cell_measurement_theta_min      2.159
_cell_volume                     5496.1(6)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2021)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            120736
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.447
_diffrn_reflns_theta_min         1.529
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              fine-focus
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.444
_exptl_absorpt_correction_T_max  0.2590
_exptl_absorpt_correction_T_min  0.2170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0596 before and 0.0539 after correction.
The Ratio of minimum to maximum transmission is 0.8378.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Purple
_exptl_crystal_colour_primary    Purple
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_description       Rod
_exptl_crystal_F_000             2084
_exptl_crystal_size_max          0.635
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.139
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     665
_refine_ls_number_reflns         10138
_refine_ls_number_restraints     80
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0450P)^2^+3.0089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7882
_reflns_number_total             10138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06573h2.cif
_cod_data_source_block           Zhang_JKB301
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1568276--1568277.cif.
;
_cod_database_code               1568276
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.766
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C6SB-C5SB = C5S-C6S
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C27) = Uanis(C27B)
Uanis(C29B) = Uanis(C29)
Uanis(C7SB) = Uanis(C7S)
4. Rigid body (RIGU) restrains
 O2S, C5S, C6S, C7S, C8S, O2SB, C5SB, C6SB, C7SB, C8SB
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C27, C28, C29, C27B, C28B, C29B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(O2SB)=Sof(C5SB)=Sof(H5SC)=Sof(H5SD)=Sof(C6SB)=Sof(H6SC)=Sof(H6SD)=
 Sof(C7SB)=Sof(H7SC)=Sof(H7SD)=Sof(C8SB)=Sof(H8SC)=Sof(H8SD)=1-FVAR(1)
 Sof(O2S)=Sof(C5S)=Sof(H5SA)=Sof(H5SB)=Sof(C6S)=Sof(H6SA)=Sof(H6SB)=Sof(C7S)=
 Sof(H7SA)=Sof(H7SB)=Sof(C8S)=Sof(H8SA)=Sof(H8SB)=FVAR(1)
 Sof(C27B)=Sof(H27B)=Sof(C28B)=Sof(H28D)=Sof(H28E)=Sof(H28F)=Sof(C29B)=
 Sof(H29D)=Sof(H29E)=Sof(H29F)=1-FVAR(2)
 Sof(C27)=Sof(H27)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=Sof(C29)=Sof(H29A)=
 Sof(H29B)=Sof(H29C)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C15(H15), C18(H18), C30(H30), C27(H27), C27B(H27B)
6.b Secondary CH2 refined with riding coordinates:
 C1C(H1CA,H1CB), C2C(H2CA,H2CB), C3C(H3CA,H3CB), C5C(H5CA,H5CB), C6C(H6CA,
 H6CB), C7C(H7CA,H7CB), C9C(H9CA,H9CB), C10C(H10A,H10B), C11C(H11A,H11B),
 C13C(H13A,H13B), C14C(H14A,H14B), C15C(H15A,H15B), C1S(H1SA,H1SB), C2S(H2SA,
 H2SB), C3S(H3SA,H3SB), C4S(H4SA,H4SB), C5S(H5SA,H5SB), C6S(H6SA,H6SB),
 C7S(H7SA,H7SB), C8S(H8SA,H8SB), C5SB(H5SC,H5SD), C6SB(H6SC,H6SD), C7SB(H7SC,
 H7SD), C8SB(H8SC,H8SD)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C23(H23), C24(H24),
 C25(H25)
6.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C28(H28A,H28B,H28C), C29(H29A,
 H29B,H29C), C28B(H28D,H28E,H28F), C29B(H29D,H29E,H29F), C4C(H4CA,H4CB,H4CC),
 C8C(H8CA,H8CB,H8CC), C12C(H12A,H12B,H12C), C16C(H16D,H16E,H16F)
;
_shelx_res_checksum              12429
_shelx_hkl_checksum              4493
_olex2_submission_special_instructions 'No special instructions were received'