#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/11/4301140.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_4301140
loop_
_publ_author_name
'Carolynne Ricardo'
'Lauren M. Matosziuk'
'Jeffrey D. Evanseck'
'Tomislav Pintauer'
_publ_section_title
;
Strong Coordination of Tetraphenylborate Anion to Copper(I) Bipyridine and
Phenanthroline-Based Complexes and Its Effect on Catalytic Activity in the
Cyclopropanation of Styrene
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              16
_journal_page_last               18
_journal_paper_doi               10.1021/ic801783r
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C34 H28 B Cu N2'
_chemical_formula_sum            'C34 H28 B Cu N2'
_chemical_formula_weight         538.93
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.185(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2143(11)
_cell_length_b                   33.258(4)
_cell_length_c                   9.2161(11)
_cell_measurement_reflns_used    3939
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      49.966
_cell_measurement_theta_min      4.833
_cell_volume                     2576.4(5)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Shedrick, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Smart ApexII'
_diffrn_measurement_method       'φ and ω Scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1323
_diffrn_reflns_av_sigmaI/netI    0.1070
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27712
_diffrn_reflns_theta_full        28.77
_diffrn_reflns_theta_max         28.77
_diffrn_reflns_theta_min         1.22
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         6651
_exptl_absorpt_coefficient_mu    0.875
_exptl_absorpt_correction_T_max  0.9254
_exptl_absorpt_correction_T_min  0.7322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhomboid
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.0405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                3986
_reflns_number_total             6651
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801783r_si_002_3.cif
_cod_data_source_block           '[Cu(bpy)][BPh4]'
_cod_original_cell_volume        2576.3(5)
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4301140
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.7346(3) 0.88327(8) 0.3188(3) 0.0167(6) Uani 1 1 d . . .
C1 C 0.8001(3) 0.87457(7) 0.5121(3) 0.0172(5) Uani 1 1 d . . .
C2 C 0.8083(3) 0.90554(8) 0.6200(3) 0.0230(6) Uani 1 1 d . . .
H20 H 0.8130 0.9332 0.5860 0.028 Uiso 1 1 calc R . .
C3 C 0.5431(3) 0.89086(7) 0.2646(3) 0.0173(5) Uani 1 1 d . . .
C4 C 0.4338(3) 0.85902(8) 0.2388(3) 0.0208(6) Uani 1 1 d . . .
H2 H 0.4620 0.8334 0.2048 0.025 Uiso 1 1 calc R . .
C5 C 0.4755(3) 0.92945(7) 0.2552(3) 0.0230(6) Uani 1 1 d . . .
H6 H 0.5415 0.9518 0.2735 0.028 Uiso 1 1 calc R . .
C6 C 0.3168(3) 0.93576(8) 0.2205(3) 0.0258(6) Uani 1 1 d . . .
H5 H 0.2790 0.9619 0.2161 0.031 Uiso 1 1 calc R . .
C7 C 0.2131(3) 0.90358(9) 0.1920(3) 0.0270(6) Uani 1 1 d . . .
H4 H 0.1060 0.9077 0.1682 0.032 Uiso 1 1 calc R . .
C8 C 0.2729(3) 0.86528(8) 0.1999(3) 0.0283(7) Uani 1 1 d . . .
H3 H 0.2048 0.8433 0.1790 0.034 Uiso 1 1 calc R . .
C9 C 0.8430(3) 0.83606(8) 0.5821(3) 0.0227(6) Uani 1 1 d . . .
H23 H 0.8371 0.8143 0.5167 0.027 Uiso 1 1 calc R . .
C10 C 0.8936(3) 0.82948(8) 0.7444(3) 0.0264(6) Uani 1 1 d . . .
H24 H 0.9212 0.8037 0.7851 0.032 Uiso 1 1 calc R . .
C11 C 0.9031(3) 0.86094(8) 0.8457(3) 0.0254(6) Uani 1 1 d . . .
H22 H 0.9373 0.8565 0.9543 0.030 Uiso 1 1 calc R . .
C12 C 0.8616(3) 0.89868(8) 0.7839(3) 0.0276(6) Uani 1 1 d . . .
H21 H 0.8688 0.9201 0.8514 0.033 Uiso 1 1 calc R . .
C13 C 0.6688(3) 0.83067(7) 0.0788(3) 0.0208(6) Uani 1 1 d . . .
H13 H 0.5688 0.8424 0.0287 0.025 Uiso 1 1 calc R . .
C14 C 0.7736(3) 0.84555(7) 0.2267(3) 0.0172(5) Uani 1 1 d . . .
C15 C 0.9244(3) 0.82742(8) 0.2906(3) 0.0226(6) Uani 1 1 d . . .
H15 H 1.0010 0.8375 0.3849 0.027 Uiso 1 1 calc R . .
C16 C 0.9639(3) 0.79504(8) 0.2190(3) 0.0245(6) Uani 1 1 d . . .
H16 H 1.0637 0.7832 0.2683 0.029 Uiso 1 1 calc R . .
C17 C 0.8563(4) 0.78032(8) 0.0750(3) 0.0260(6) Uani 1 1 d . . .
H17 H 0.8818 0.7585 0.0270 0.031 Uiso 1 1 calc R . .
C18 C 0.7093(3) 0.79887(8) 0.0040(3) 0.0246(6) Uani 1 1 d . . .
H18 H 0.6368 0.7900 -0.0949 0.030 Uiso 1 1 calc R . .
C19 C 0.4276(4) 0.94011(9) 0.6549(3) 0.0319(7) Uani 1 1 d . . .
H30 H 0.4786 0.9583 0.6150 0.038 Uiso 1 1 calc R . .
C20 C 0.3507(4) 0.95442(9) 0.7447(3) 0.0341(7) Uani 1 1 d . . .
H31 H 0.3501 0.9818 0.7648 0.041 Uiso 1 1 calc R . .
C21 C 0.2751(3) 0.92795(8) 0.8039(3) 0.0297(7) Uani 1 1 d . . .
H32 H 0.2242 0.9370 0.8665 0.036 Uiso 1 1 calc R . .
C22 C 0.2756(3) 0.88799(8) 0.7697(3) 0.0268(6) Uani 1 1 d . . .
H33 H 0.2231 0.8696 0.8073 0.032 Uiso 1 1 calc R . .
C23 C 0.3550(3) 0.87495(8) 0.6786(3) 0.0207(5) Uani 1 1 d . . .
C24 C 0.3646(3) 0.83191(8) 0.6398(3) 0.0203(6) Uani 1 1 d . . .
C25 C 0.2721(3) 0.80200(8) 0.6654(3) 0.0278(6) Uani 1 1 d . . .
H28 H 0.1984 0.8084 0.7068 0.033 Uiso 1 1 calc R . .
C26 C 0.2911(4) 0.76249(9) 0.6283(4) 0.0321(7) Uani 1 1 d . . .
H27 H 0.2300 0.7421 0.6440 0.039 Uiso 1 1 calc R . .
C27 C 0.4016(4) 0.75390(9) 0.5681(3) 0.0303(7) Uani 1 1 d . . .
H26 H 0.4179 0.7276 0.5440 0.036 Uiso 1 1 calc R . .
C28 C 0.4878(4) 0.78522(8) 0.5444(3) 0.0293(7) Uani 1 1 d . . .
H25 H 0.5620 0.7794 0.5029 0.035 Uiso 1 1 calc R . .
C29 C 0.8153(3) 0.92294(7) 0.2762(3) 0.0181(5) Uani 1 1 d . . .
C30 C 0.9516(3) 0.94265(8) 0.3807(3) 0.0217(6) Uani 1 1 d . . .
H11 H 1.0007 0.9338 0.4854 0.026 Uiso 1 1 calc R . .
C31 C 1.0161(3) 0.97509(8) 0.3333(4) 0.0263(6) Uani 1 1 d . . .
H12 H 1.1069 0.9876 0.4065 0.032 Uiso 1 1 calc R . .
C32 C 0.7494(3) 0.93792(8) 0.1206(3) 0.0219(6) Uani 1 1 d . . .
H8 H 0.6590 0.9255 0.0463 0.026 Uiso 1 1 calc R . .
C33 C 0.9477(3) 0.98899(8) 0.1799(4) 0.0276(7) Uani 1 1 d . . .
H10 H 0.9917 1.0107 0.1485 0.033 Uiso 1 1 calc R . .
C34 C 0.8127(4) 0.97030(8) 0.0728(3) 0.0258(6) Uani 1 1 d . . .
H9 H 0.7643 0.9795 -0.0315 0.031 Uiso 1 1 calc R . .
Cu1 Cu 0.56243(4) 0.873929(11) 0.51502(4) 0.02834(12) Uani 1 1 d . . .
N2 N 0.4700(3) 0.82335(6) 0.5779(3) 0.0233(5) Uani 1 1 d . . .
N1 N 0.4320(3) 0.90083(7) 0.6226(3) 0.0245(5) Uani 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'
N N 0.0061 0.0033 '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'
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
C14 B1 C29 106.0(2) . . ?
C14 B1 C3 113.4(2) . . ?
C29 B1 C3 109.8(2) . . ?
C14 B1 C1 111.3(2) . . ?
C29 B1 C1 113.4(2) . . ?
C3 B1 C1 103.1(2) . . ?
C2 C1 C9 114.5(2) . . ?
C2 C1 B1 121.4(2) . . ?
C9 C1 B1 124.0(2) . . ?
C2 C1 Cu1 76.42(15) . . ?
C9 C1 Cu1 94.54(16) . . ?
B1 C1 Cu1 95.11(15) . . ?
C12 C2 C1 122.3(2) . . ?
C12 C2 Cu1 103.13(18) . . ?
C1 C2 Cu1 67.29(14) . . ?
C12 C2 H20 117.1 . . ?
C1 C2 H20 117.1 . . ?
Cu1 C2 H20 117.1 . . ?
C4 C3 C5 113.8(2) . . ?
C4 C3 B1 122.6(2) . . ?
C5 C3 B1 123.3(2) . . ?
C4 C3 Cu1 75.12(15) . . ?
C5 C3 Cu1 97.68(16) . . ?
B1 C3 Cu1 91.44(15) . . ?
C8 C4 C3 122.9(2) . . ?
C8 C4 Cu1 104.80(17) . . ?
C3 C4 Cu1 69.85(14) . . ?
C8 C4 H2 116.2 . . ?
C3 C4 H2 116.2 . . ?
Cu1 C4 H2 116.2 . . ?
C6 C5 C3 123.5(2) . . ?
C6 C5 H6 118.3 . . ?
C3 C5 H6 118.3 . . ?
C5 C6 C7 120.6(2) . . ?
C5 C6 H5 119.7 . . ?
C7 C6 H5 119.7 . . ?
C8 C7 C6 118.3(3) . . ?
C8 C7 H4 120.9 . . ?
C6 C7 H4 120.9 . . ?
C7 C8 C4 120.8(3) . . ?
C7 C8 H3 119.6 . . ?
C4 C8 H3 119.6 . . ?
C10 C9 C1 122.7(2) . . ?
C10 C9 H23 118.6 . . ?
C1 C9 H23 118.6 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H24 119.7 . . ?
C9 C10 H24 119.7 . . ?
C12 C11 C10 119.0(2) . . ?
C12 C11 H22 120.5 . . ?
C10 C11 H22 120.5 . . ?
C11 C12 C2 120.9(3) . . ?
C11 C12 H21 119.6 . . ?
C2 C12 H21 119.6 . . ?
C18 C13 C14 122.1(3) . . ?
C18 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C13 C14 C15 115.2(2) . . ?
C13 C14 B1 124.5(2) . . ?
C15 C14 B1 120.2(2) . . ?
C16 C15 C14 122.8(3) . . ?
C16 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 118.4(2) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C17 C18 C13 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
N1 C19 C20 122.6(3) . . ?
N1 C19 H30 118.7 . . ?
C20 C19 H30 118.7 . . ?
C21 C20 C19 119.3(3) . . ?
C21 C20 H31 120.3 . . ?
C19 C20 H31 120.3 . . ?
C22 C21 C20 118.9(3) . . ?
C22 C21 H32 120.5 . . ?
C20 C21 H32 120.5 . . ?
C21 C22 C23 119.7(3) . . ?
C21 C22 H33 120.1 . . ?
C23 C22 H33 120.1 . . ?
N1 C23 C22 121.5(3) . . ?
N1 C23 C24 115.5(2) . . ?
C22 C23 C24 123.0(2) . . ?
N2 C24 C25 121.3(2) . . ?
N2 C24 C23 115.6(2) . . ?
C25 C24 C23 123.1(2) . . ?
C26 C25 C24 119.2(3) . . ?
C26 C25 H28 120.4 . . ?
C24 C25 H28 120.4 . . ?
C27 C26 C25 119.1(3) . . ?
C27 C26 H27 120.5 . . ?
C25 C26 H27 120.5 . . ?
C26 C27 C28 118.4(3) . . ?
C26 C27 H26 120.8 . . ?
C28 C27 H26 120.8 . . ?
N2 C28 C27 123.3(3) . . ?
N2 C28 H25 118.4 . . ?
C27 C28 H25 118.4 . . ?
C30 C29 C32 115.5(2) . . ?
C30 C29 B1 125.6(2) . . ?
C32 C29 B1 118.8(2) . . ?
C31 C30 C29 122.0(3) . . ?
C31 C30 H11 119.0 . . ?
C29 C30 H11 119.0 . . ?
C33 C31 C30 120.8(3) . . ?
C33 C31 H12 119.6 . . ?
C30 C31 H12 119.6 . . ?
C34 C32 C29 122.8(3) . . ?
C34 C32 H8 118.6 . . ?
C29 C32 H8 118.6 . . ?
C31 C33 C34 119.0(2) . . ?
C31 C33 H10 120.5 . . ?
C34 C33 H10 120.5 . . ?
C33 C34 C32 119.9(3) . . ?
C33 C34 H9 120.0 . . ?
C32 C34 H9 120.0 . . ?
N1 Cu1 N2 80.18(9) . . ?
N1 Cu1 C1 141.71(9) . . ?
N2 Cu1 C1 122.42(9) . . ?
N1 Cu1 C3 123.79(9) . . ?
N2 Cu1 C3 127.21(9) . . ?
C1 Cu1 C3 69.83(9) . . ?
N1 Cu1 C2 105.45(9) . . ?
N2 Cu1 C2 133.98(9) . . ?
C1 Cu1 C2 36.29(9) . . ?
C3 Cu1 C2 88.21(9) . . ?
N1 Cu1 C4 118.33(9) . . ?
N2 Cu1 C4 92.77(9) . . ?
C1 Cu1 C4 92.92(9) . . ?
C3 Cu1 C4 35.03(9) . . ?
C2 Cu1 C4 120.95(9) . . ?
C28 N2 C24 118.7(2) . . ?
C28 N2 Cu1 127.21(19) . . ?
C24 N2 Cu1 113.46(17) . . ?
C19 N1 C23 117.9(2) . . ?
C19 N1 Cu1 127.43(19) . . ?
C23 N1 Cu1 114.34(18) . . ?
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
B1 C14 1.635(4) . ?
B1 C29 1.640(4) . ?
B1 C3 1.644(4) . ?
B1 C1 1.656(4) . ?
C1 C2 1.412(3) . ?
C1 C9 1.416(3) . ?
C1 Cu1 2.201(3) . ?
C2 C12 1.402(4) . ?
C2 Cu1 2.319(3) . ?
C2 H20 0.9800 . ?
C3 C4 1.413(4) . ?
C3 C5 1.414(3) . ?
C3 Cu1 2.311(2) . ?
C4 C8 1.391(4) . ?
C4 Cu1 2.379(3) . ?
C4 H2 0.9800 . ?
C5 C6 1.378(4) . ?
C5 H6 0.9300 . ?
C6 C7 1.386(4) . ?
C6 H5 0.9300 . ?
C7 C8 1.378(4) . ?
C7 H4 0.9300 . ?
C8 H3 0.9300 . ?
C9 C10 1.389(4) . ?
C9 H23 0.9300 . ?
C10 C11 1.381(4) . ?
C10 H24 0.9300 . ?
C11 C12 1.367(4) . ?
C11 H22 0.9300 . ?
C12 H21 0.9300 . ?
C13 C18 1.395(3) . ?
C13 C14 1.399(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.404(4) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N1 1.344(3) . ?
C19 C20 1.376(4) . ?
C19 H30 0.9300 . ?
C20 C21 1.367(4) . ?
C20 H31 0.9300 . ?
C21 C22 1.366(4) . ?
C21 H32 0.9300 . ?
C22 C23 1.390(4) . ?
C22 H33 0.9300 . ?
C23 N1 1.346(3) . ?
C23 C24 1.487(4) . ?
C24 N2 1.343(3) . ?
C24 C25 1.392(4) . ?
C25 C26 1.387(4) . ?
C25 H28 0.9300 . ?
C26 C27 1.374(4) . ?
C26 H27 0.9300 . ?
C27 C28 1.381(4) . ?
C27 H26 0.9300 . ?
C28 N2 1.331(3) . ?
C28 H25 0.9300 . ?
C29 C30 1.394(4) . ?
C29 C32 1.400(3) . ?
C30 C31 1.386(4) . ?
C30 H11 0.9300 . ?
C31 C33 1.371(4) . ?
C31 H12 0.9300 . ?
C32 C34 1.380(4) . ?
C32 H8 0.9300 . ?
C33 C34 1.379(4) . ?
C33 H10 0.9300 . ?
C34 H9 0.9300 . ?
Cu1 N1 2.051(2) . ?
Cu1 N2 2.072(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139126304
