Synthesis, characterization, and photoluminescent studies of three-coordinate Cu(i)‒NHC complexes bearing unsymmetrically-substituted dipyridylamine ligands
Glinton, Kwame; Latifi, Reza; Cockrell, David S.; Bardeaux, Matthew; Nguyen, Bachkhoa; Tahsini, Laleh; RSC Advances 9 (2019) 22417–; doi:10.1039/C9RA04886C

data_7233227
_publ_section_title
;
 Synthesis, characterization, and photoluminescent studies of
 three-coordinate Cu(i)--NHC complexes bearing unsymmetrically-substituted
 dipyridylamine ligands
;
_journal_issue                   39
_journal_name_full               'RSC Advances'
_journal_page_first              22417
_journal_paper_doi               10.1039/C9RA04886C
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety
'0.5(C57 H66 Cu N4), 0.5(C57 H65 Cu N4), 1.5(C H2 Cl2), F6 P'
_chemical_formula_sum            'C58.5 H68.5 Cl3 Cu F6 N4 P'
_chemical_formula_weight         1142.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-04 deposited with the CCDC.    2019-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                87.913(15)
_cell_angle_beta                 80.698(14)
_cell_angle_gamma                71.923(14)
_cell_formula_units_Z            4
_cell_length_a                   12.683(11)
_cell_length_b                   18.454(16)
_cell_length_c                   25.59(2)
_cell_measurement_reflns_used    9367
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.20
_cell_volume                     5618(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            97454
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         0.806
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1372 before and 0.0739 after correction.
The Ratio of minimum to maximum transmission is 0.6841.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic brownish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             2386
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.122
_refine_diff_density_max         1.388
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.092
_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     1429
_refine_ls_number_reflns         23779
_refine_ls_number_restraints     133
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0625
_refine_ls_shift/su_max          0.075
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0957P)^2^+5.4060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.1936
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15529
_reflns_number_total             23779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra04886c2.cif
_cod_data_source_block           lt_iii_149_5runs
_cod_original_cell_volume        5618(9)
_cod_original_formula_sum        'C58.50 H68.50 Cl3 Cu F6 N4 P'
_cod_database_code               7233227
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.913
_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
 Cl1A-C0AA \\sim Cl0A-C0AA \\sim Cl1-C7 \\sim Cl2-C7 \\sim Cl06-C03R \\sim
Cl05-C03R \\sim Cl2A-C7A ~
 Cl1-C7 \\sim Cl3A-C7A \\sim Cl2-C7
 with sigma of 0.01
 Cl1A-C0AA \\sim Cl1B-C0AB
 with sigma of 0.02
 Cl0A-C0AA \\sim Cl0B-C0AB
 with sigma of 0.02
 Cl1A-Cl0A \\sim Cl1B-Cl0B
 with sigma of 0.04
 C01Z-C0 \\sim C043-C01Z \\sim C045-C01Z \\sim C01Z-C1
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Cl0A \\sim Cl1A \\sim C0AA \\sim Cl0B \\sim Cl1B \\sim C0AB: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 Cl0A, Cl1A, C0AA, Cl1, Cl2, C7, Cl2A, Cl3A, C7A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl0A, Cl1A, C0AA, Cl0B, Cl1B, C0AB
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(Cl2A)=Sof(Cl3A)=Sof(C7A)=Sof(H7AB)=Sof(H7AC)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(C7)=Sof(H7A)=Sof(H7B)=FVAR(1)
 Sof(Cl0B)=Sof(Cl1B)=Sof(C0AB)=Sof(H0AD)=Sof(H0AE)=1-FVAR(2)
 Sof(Cl0A)=Sof(Cl1A)=Sof(C0AA)=Sof(H0AB)=Sof(H0AC)=FVAR(2)
 Sof(C0)=Sof(H0A)=Sof(H0B)=Sof(H0C)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=1-FVAR(3)
 Sof(C043)=Sof(H04A)=Sof(H04B)=Sof(H04C)=Sof(C045)=Sof(H04D)=Sof(H04E)=
 Sof(H04F)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C02N(H02P), C02S(H02S), C03F(H2AA), C023(H023), C02J(H02J), C02Y(H02Y),
 C02Z(H02Z)
6.b Secondary CH2 refined with riding coordinates:
 C02B(H02H,H02I), C025(H02R,H02V), C01S(H01A,H01B), C028(H02D,H02E), C0AA(H0AB,
 H0AC), C0AB(H0AD,H0AE), C7(H7A,H7B), C7A(H7AB,H7AC), C03R(H5BA,H7BA)
6.c Aromatic/amide H refined with riding coordinates:
 C00V(H00V), C01F(H01F), C01I(H01I), C01K(H01K), C01X(H01X), C02A(H02G),
 C02M(H02N), C02P(H02Q), C02U(H02U), C02X(H02X), C03G(H3AA), C03L(H4AA),
 C03P(H7AA), C029(H029), C031(H031), C034(H034), C01E(H01E), C01P(H01P),
 C01R(H01R), C01T(H01T), C01V(H01V), C01W(H01W), C01Y(H01Y), C02F(H02F),
 C02O(H02O), C02T(H02T), C02W(H02W), C021(H021), C030(H030), C033(H033),
 C035(H035), C036(H036)
6.d Idealised Me refined as rotating group:
 C01L(H01C,H01D,H01G), C02L(H02K,H02L,H02M), C03B(H0AA,H,HA), C03D(H1AA,HB,HC),
  C03M(H5AA,HD,HE), C03N(H6AA,HF,HG), C03Q(H8AA,HH,HI), C03S(H9AA,HJ,HK),
 C03T(H0BA,HL,HM), C03U(H1BA,HN,HO), C03Y(H2BA,HP,HQ), C03Z(H3BA,HR,HS),
 C038(H4BA,HT,HU), C041(H04G,H04H,H04I), C0(H0A,H0B,H0C), C1(H1A,H1B,H1C),
 C02H(H02A,H02B,H02C), C03A(H03A,H03B,H03C), C03C(H03D,H03E,H03F), C03E(H03G,
 H03H,H03I), C03H(H03J,H03K,H03L), C03I(H03M,H03N,H03O), C03J(H03P,H03Q,H03R),
 C03O(H03S,H03T,H03U), C03V(H03V,H03W,H03X), C03W(H03Y,HV,HW), C03X(H03Z,HX,HY),
  C039(H03,HZ,H6BA), C043(H04A,H04B,H04C), C045(H04D,H04E,H04F)
;
_olex2_submission_special_instructions 'No special instructions were received'