#------------------------------------------------------------------------------
#$Date: 2022-07-06 10:53:41 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276587 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567002.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1567002
loop_
_publ_author_name
'Noonikara-Poyil, Anurag'
'Ridlen, Shawn G.'
'Fernández, Israel'
'Dias, H. V. Rasika'
_publ_section_title
;
 Isolable acetylene complexes of copper and silver
;
_journal_issue                   24
_journal_name_full               'Chemical Science'
_journal_page_first              7190
_journal_page_last               7203
_journal_paper_doi               10.1039/D2SC02377F
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C13 H18 Cu N4, B F4'
_chemical_formula_sum            'C13 H18 B Cu F4 N4'
_chemical_formula_weight         380.66
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-02-16 deposited with the CCDC.	2022-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                107.079(2)
_cell_angle_beta                 100.3190(10)
_cell_angle_gamma                102.0130(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9267(5)
_cell_length_b                   10.4752(7)
_cell_length_c                   10.6827(7)
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      32.26
_cell_measurement_theta_min      2.72
_cell_volume                     801.49(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Photon 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.6 mm double-pinhole'
_diffrn_radiation_detector       'Photon 100 CMOS'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27886
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.128
_diffrn_reflns_theta_min         2.718
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              'KFF MO-2KC-90'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.405
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0981 before and 0.0730 after correction.
The Ratio of minimum to maximum transmission is 0.8671.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+2.6863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3605
_reflns_number_total             4311
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc02377f3.cif
_cod_data_source_block           rad840_0m_a
_cod_depositor_comments
'Adding full bibliography for 1567002--1567006.cif.'
_cod_database_code               1567002
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.972
_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.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C4(H4A,H4B,H4C), C10(H10A,H10B,H10C), C5(H5A,H5B,H5C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.43845(4) 0.45684(3) 0.70954(4) 0.01098(9) Uani 1 1 d . . . . .
F1 F 0.1461(2) 0.29958(18) 0.47354(17) 0.0199(4) Uani 1 1 d . . . . .
F3 F -0.1436(2) 0.19712(19) 0.3499(2) 0.0268(4) Uani 1 1 d . . . . .
F2 F 0.0804(3) 0.2099(2) 0.24436(19) 0.0298(5) Uani 1 1 d . . . . .
F4 F 0.0466(2) 0.06642(18) 0.3664(2) 0.0241(4) Uani 1 1 d . . . . .
N3 N 0.4946(3) 0.1886(2) 0.6884(2) 0.0103(4) Uani 1 1 d . . . . .
N1 N 0.2843(3) 0.2487(2) 0.8134(2) 0.0119(4) Uani 1 1 d . . . . .
N4 N 0.5675(3) 0.3127(2) 0.6741(2) 0.0103(4) Uani 1 1 d . . . . .
N2 N 0.2926(3) 0.3814(2) 0.8171(2) 0.0124(4) Uani 1 1 d . . . . .
C13 C 0.5245(4) 0.6143(3) 0.6504(3) 0.0173(6) Uani 1 1 d . . . . .
C9 C 0.8566(3) 0.4290(3) 0.6455(3) 0.0138(5) Uani 1 1 d . . . . .
H9A H 0.809647 0.437996 0.558108 0.021 Uiso 1 1 calc R U . . .
H9B H 0.974029 0.412063 0.648865 0.021 Uiso 1 1 calc R U . . .
H9C H 0.867761 0.514957 0.718898 0.021 Uiso 1 1 calc R U . . .
C12 C 0.3988(4) 0.6320(3) 0.6948(3) 0.0165(6) Uani 1 1 d . . . . .
C6 C 0.7324(3) 0.3106(3) 0.6616(3) 0.0107(5) Uani 1 1 d . . . . .
C8 C 0.6102(4) 0.1092(3) 0.6835(3) 0.0129(5) Uani 1 1 d . . . . .
C1 C 0.2545(4) 0.4444(3) 0.9330(3) 0.0151(5) Uani 1 1 d . . . . .
C3 C 0.2419(4) 0.2279(3) 0.9249(3) 0.0155(6) Uani 1 1 d . . . . .
C11 C 0.3106(3) 0.1534(3) 0.6941(3) 0.0125(5) Uani 1 1 d . . . . .
H11A H 0.275661 0.057544 0.695432 0.015 Uiso 1 1 calc R U . . .
H11B H 0.233178 0.156578 0.611944 0.015 Uiso 1 1 calc R U . . .
C2 C 0.2215(4) 0.3513(3) 1.0017(3) 0.0176(6) Uani 1 1 d . . . . .
H2 H 0.190666 0.369782 1.085951 0.021 Uiso 1 1 calc R U . . .
C7 C 0.7632(4) 0.1856(3) 0.6672(3) 0.0140(5) Uani 1 1 d . . . . .
H7 H 0.869491 0.158541 0.661042 0.017 Uiso 1 1 calc R U . . .
C4 C 0.2524(4) 0.5928(3) 0.9729(3) 0.0194(6) Uani 1 1 d . . . . .
H4A H 0.373444 0.652177 0.990749 0.029 Uiso 1 1 calc R U . . .
H4B H 0.209423 0.617352 1.054869 0.029 Uiso 1 1 calc R U . . .
H4C H 0.172974 0.606334 0.899272 0.029 Uiso 1 1 calc R U . . .
C10 C 0.5645(4) -0.0318(3) 0.6934(3) 0.0197(6) Uani 1 1 d . . . . .
H10A H 0.528419 -0.026595 0.777465 0.030 Uiso 1 1 calc R U . . .
H10B H 0.668818 -0.068186 0.693586 0.030 Uiso 1 1 calc R U . . .
H10C H 0.465928 -0.093743 0.615689 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2279(5) 0.0943(3) 0.9507(3) 0.0252(7) Uani 1 1 d . . . . .
H5A H 0.121843 0.023599 0.886675 0.038 Uiso 1 1 calc R U . . .
H5B H 0.218135 0.107686 1.043526 0.038 Uiso 1 1 calc R U . . .
H5C H 0.334583 0.063833 0.938726 0.038 Uiso 1 1 calc R U . . .
B B 0.0320(4) 0.1937(3) 0.3584(3) 0.0139(6) Uani 1 1 d . . . . .
H13 H 0.611(5) 0.626(4) 0.614(4) 0.035(11) Uiso 1 1 d . . . . .
H12 H 0.309(6) 0.670(4) 0.716(4) 0.044(12) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu N4 97.14(9) . . ?
C13 Cu N4 114.63(11) . . ?
C13 Cu N2 147.43(11) . . ?
C13 Cu C12 35.55(13) . . ?
C12 Cu N4 150.11(11) . . ?
C12 Cu N2 112.67(11) . . ?
N4 N3 C11 119.5(2) . . ?
C8 N3 N4 111.4(2) . . ?
C8 N3 C11 128.8(2) . . ?
N2 N1 C11 117.8(2) . . ?
C3 N1 N2 111.3(2) . . ?
C3 N1 C11 130.8(2) . . ?
N3 N4 Cu 117.81(16) . . ?
C6 N4 Cu 135.33(18) . . ?
C6 N4 N3 105.6(2) . . ?
N1 N2 Cu 117.55(17) . . ?
C1 N2 Cu 131.1(2) . . ?
C1 N2 N1 105.8(2) . . ?
Cu C13 H13 126(3) . . ?
C12 C13 Cu 72.24(19) . . ?
C12 C13 H13 162(3) . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
Cu C12 H12 128(3) . . ?
C13 C12 Cu 72.20(19) . . ?
C13 C12 H12 160(3) . . ?
N4 C6 C9 122.1(2) . . ?
N4 C6 C7 109.9(2) . . ?
C7 C6 C9 128.0(2) . . ?
N3 C8 C7 106.2(2) . . ?
N3 C8 C10 122.8(2) . . ?
C7 C8 C10 131.0(3) . . ?
N2 C1 C2 109.7(3) . . ?
N2 C1 C4 121.3(3) . . ?
C2 C1 C4 129.0(3) . . ?
N1 C3 C2 106.2(2) . . ?
N1 C3 C5 123.4(3) . . ?
C2 C3 C5 130.4(3) . . ?
N3 C11 N1 111.2(2) . . ?
N3 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
N1 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C1 C2 H2 126.5 . . ?
C3 C2 C1 107.1(3) . . ?
C3 C2 H2 126.5 . . ?
C6 C7 H7 126.5 . . ?
C8 C7 C6 106.9(2) . . ?
C8 C7 H7 126.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
F3 B F1 110.5(2) . . ?
F3 B F2 109.7(3) . . ?
F3 B F4 108.7(2) . . ?
F2 B F1 109.2(2) . . ?
F2 B F4 109.6(2) . . ?
F4 B F1 109.0(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu N4 1.978(2) . ?
Cu N2 1.977(2) . ?
Cu C13 1.970(3) . ?
Cu C12 1.971(3) . ?
F1 B 1.394(4) . ?
F3 B 1.387(3) . ?
F2 B 1.387(4) . ?
F4 B 1.387(3) . ?
N3 N4 1.372(3) . ?
N3 C8 1.358(3) . ?
N3 C11 1.445(3) . ?
N1 N2 1.367(3) . ?
N1 C3 1.358(3) . ?
N1 C11 1.449(3) . ?
N4 C6 1.342(3) . ?
N2 C1 1.341(4) . ?
C13 C12 1.203(4) . ?
C13 H13 0.85(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C6 1.488(4) . ?
C12 H12 0.92(4) . ?
C6 C7 1.397(4) . ?
C8 C7 1.377(4) . ?
C8 C10 1.486(4) . ?
C1 C2 1.394(4) . ?
C1 C4 1.490(4) . ?
C3 C2 1.372(4) . ?
C3 C5 1.490(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C2 H2 0.9500 . ?
C7 H7 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu N4 C6 C9 -13.1(4) . . . . ?
Cu N4 C6 C7 166.5(2) . . . . ?
Cu N2 C1 C2 -152.5(2) . . . . ?
Cu N2 C1 C4 27.2(4) . . . . ?
N3 N4 C6 C9 -179.3(2) . . . . ?
N3 N4 C6 C7 0.3(3) . . . . ?
N3 C8 C7 C6 -0.6(3) . . . . ?
N1 N2 C1 C2 -0.3(3) . . . . ?
N1 N2 C1 C4 179.4(2) . . . . ?
N1 C3 C2 C1 -0.5(3) . . . . ?
N4 N3 C8 C7 0.8(3) . . . . ?
N4 N3 C8 C10 -178.7(3) . . . . ?
N4 N3 C11 N1 -64.6(3) . . . . ?
N4 C6 C7 C8 0.2(3) . . . . ?
N2 N1 C3 C2 0.4(3) . . . . ?
N2 N1 C3 C5 -178.3(3) . . . . ?
N2 N1 C11 N3 71.3(3) . . . . ?
N2 C1 C2 C3 0.5(3) . . . . ?
C9 C6 C7 C8 179.7(3) . . . . ?
C8 N3 N4 Cu -169.75(18) . . . . ?
C8 N3 N4 C6 -0.7(3) . . . . ?
C8 N3 C11 N1 121.8(3) . . . . ?
C3 N1 N2 Cu 156.62(18) . . . . ?
C3 N1 N2 C1 -0.1(3) . . . . ?
C3 N1 C11 N3 -112.7(3) . . . . ?
C11 N3 N4 Cu 15.6(3) . . . . ?
C11 N3 N4 C6 -175.3(2) . . . . ?
C11 N3 C8 C7 174.8(3) . . . . ?
C11 N3 C8 C10 -4.6(4) . . . . ?
C11 N1 N2 Cu -26.6(3) . . . . ?
C11 N1 N2 C1 176.7(2) . . . . ?
C11 N1 C3 C2 -175.9(3) . . . . ?
C11 N1 C3 C5 5.4(5) . . . . ?
C4 C1 C2 C3 -179.2(3) . . . . ?
C10 C8 C7 C6 178.8(3) . . . . ?
C5 C3 C2 C1 178.1(3) . . . . ?
