#------------------------------------------------------------------------------
#$Date: 2022-09-15 11:50:56 +0300 (Thu, 15 Sep 2022) $
#$Revision: 277867 $
#$URL: file:///home/coder/svn-repositories/cod/cif/5/00/02/5000297.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_5000297
loop_
_publ_author_name
'Tilak Chandra'
'Maren Pink'
'Jeffrey M. Zaleski'
_publ_section_title
;
Macrocyclic Metalloenediynes of Cu(II) and Zn(II): A Thermal Reactivity
Comparison
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5878
_journal_page_last               5885
_journal_paper_doi               10.1021/ic010424+
_journal_volume                  40
_journal_year                    2001
_chemical_formula_moiety         '(C48 H50 N4), 2(B F4)'
_chemical_formula_sum            'C48 H50 B2 F8 N4'
_chemical_formula_weight         856.54
_chemical_melting_point          ?
_chemical_name_common            MSC01007
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                93.640(2)
_cell_angle_beta                 106.299(2)
_cell_angle_gamma                110.788(2)
_cell_formula_units_Z            1
_cell_length_a                   9.0324(7)
_cell_length_b                   10.5874(8)
_cell_length_c                   12.5495(10)
_cell_measurement_reflns_used    842
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.46
_cell_volume                     1058.95(14)
_diffrn_ambient_temperature      115(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 44.52
_diffrn_detector_type            'Bruker SMART 6000'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
'0.30 degree frames measured for 5 seconds each'
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'Bruker Platform goniometer'
_diffrn_measurement_method       '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  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0772
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19722
_diffrn_reflns_theta_full        30.05
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  208
_diffrn_standards_number         843
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         6185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; calc
 [0.00000+1.00000exp(1.00(sinθ/λ)²)]/
   [σ²(Fo²)+0.0000+0.0500*P+(0.0524P)²+0.0000sinθ/λ]
 where P = 0.33333Fo² + 0.66667Fc²
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1229
_reflns_number_gt                3480
_reflns_number_total             6185
_reflns_threshold_expression     >2sigma(I)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'multi-scans' was replaced
with 'multi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               5000297
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B -0.1040(2) 0.46247(19) 0.66687(17) 0.0232(4) Uani 1 1 d . . .
F1 F -0.00034(13) 0.38934(10) 0.67248(10) 0.0375(3) Uani 1 1 d . . .
F2 F -0.26825(13) 0.37046(11) 0.63824(11) 0.0440(3) Uani 1 1 d . . .
F3 F -0.05578(16) 0.54542(13) 0.76957(10) 0.0497(3) Uani 1 1 d . . .
F4 F -0.08575(15) 0.54438(13) 0.58600(10) 0.0469(3) Uani 1 1 d . . .
N1 N -0.26466(16) -0.32256(13) 0.35867(11) 0.0196(3) Uani 1 1 d . . .
H1N H -0.209(2) -0.3697(19) 0.3325(16) 0.035(5) Uiso 1 1 d . . .
N2 N -0.42180(16) -0.59040(13) 0.23828(11) 0.0203(3) Uani 1 1 d . . .
C1 C -0.4902(2) -0.09575(17) 0.66314(14) 0.0242(3) Uani 1 1 d . . .
C2 C -0.3932(2) 0.03597(17) 0.64674(14) 0.0236(3) Uani 1 1 d . . .
H2 H -0.413(2) 0.1137(18) 0.6743(14) 0.023(5) Uiso 1 1 d . . .
C3 C -0.2798(2) 0.05928(17) 0.59341(14) 0.0238(3) Uani 1 1 d . . .
H3 H -0.219(2) 0.1496(19) 0.5837(15) 0.030(5) Uiso 1 1 d . . .
C4 C -0.2393(2) -0.04488(16) 0.54604(14) 0.0225(3) Uani 1 1 d . . .
C5 C -0.1970(2) -0.12604(16) 0.50537(14) 0.0225(3) Uani 1 1 d . . .
C6 C -0.1324(2) -0.21639(16) 0.45817(14) 0.0219(3) Uani 1 1 d . . .
H6A H -0.088(2) -0.2660(18) 0.5158(15) 0.026(5) Uiso 1 1 d . . .
H6B H -0.044(2) -0.1651(17) 0.4287(14) 0.021(4) Uiso 1 1 d . . .
C7 C -0.3954(2) -0.42628(16) 0.39651(14) 0.0205(3) Uani 1 1 d . . .
H7A H -0.455(2) -0.3799(17) 0.4217(14) 0.018(4) Uiso 1 1 d . . .
H7B H -0.330(2) -0.4532(17) 0.4604(14) 0.019(4) Uiso 1 1 d . . .
C8 C -0.5144(2) -0.54577(16) 0.30096(14) 0.0209(3) Uani 1 1 d . . .
H8A H -0.580(2) -0.6187(18) 0.3331(15) 0.024(5) Uiso 1 1 d . . .
H8B H -0.596(2) -0.5197(17) 0.2488(15) 0.021(4) Uiso 1 1 d . . .
C9 C -0.3217(2) -0.66117(17) 0.30257(14) 0.0223(3) Uani 1 1 d . . .
H9A H -0.247(2) -0.6724(18) 0.2577(15) 0.025(5) Uiso 1 1 d . . .
H9B H -0.244(2) -0.6007(18) 0.3764(16) 0.026(5) Uiso 1 1 d . . .
C10 C -0.4227(2) -0.79502(17) 0.32341(14) 0.0232(3) Uani 1 1 d . . .
C11 C -0.3416(2) -0.25894(17) 0.26523(14) 0.0231(3) Uani 1 1 d . . .
H11A H -0.408(2) -0.3338(18) 0.2007(15) 0.022(4) Uiso 1 1 d . . .
H11B H -0.411(2) -0.2255(18) 0.2911(15) 0.024(5) Uiso 1 1 d . . .
C12 C -0.2149(2) -0.14611(16) 0.23211(14) 0.0225(3) Uani 1 1 d . . .
C13 C -0.2038(2) -0.01116(18) 0.25258(16) 0.0284(4) Uani 1 1 d . . .
H13 H -0.273(3) 0.006(2) 0.2926(17) 0.040(6) Uiso 1 1 d . . .
C14 C -0.0957(2) 0.09303(19) 0.21666(17) 0.0333(4) Uani 1 1 d . . .
H14 H -0.085(3) 0.187(2) 0.2320(17) 0.043(6) Uiso 1 1 d . . .
C15 C 0.0030(2) 0.0637(2) 0.16038(17) 0.0343(4) Uani 1 1 d . . .
H15 H 0.077(3) 0.134(2) 0.1380(17) 0.043(6) Uiso 1 1 d . . .
C16 C -0.0051(2) -0.0690(2) 0.14064(16) 0.0323(4) Uani 1 1 d . . .
H16 H 0.065(3) -0.094(2) 0.0989(19) 0.053(7) Uiso 1 1 d . . .
C17 C -0.1138(2) -0.17362(18) 0.17626(14) 0.0263(4) Uani 1 1 d . . .
H17 H -0.121(2) -0.268(2) 0.1586(16) 0.033(5) Uiso 1 1 d . . .
C18 C -0.5319(2) -0.67492(17) 0.12667(14) 0.0234(3) Uani 1 1 d . . .
H18A H -0.606(2) -0.6275(18) 0.0900(15) 0.024(5) Uiso 1 1 d . . .
H18B H -0.605(2) -0.7681(19) 0.1318(15) 0.025(5) Uiso 1 1 d . . .
C19 C -0.4314(2) -0.68625(16) 0.05131(13) 0.0228(3) Uani 1 1 d . . .
C20 C -0.3203(2) -0.56775(18) 0.03081(14) 0.0270(4) Uani 1 1 d . . .
H20 H -0.312(2) -0.4769(18) 0.0645(15) 0.025(5) Uiso 1 1 d . . .
C21 C -0.2273(2) -0.57512(19) -0.03884(15) 0.0297(4) Uani 1 1 d . . .
H21 H -0.149(3) -0.493(2) -0.0543(18) 0.048(6) Uiso 1 1 d . . .
C22 C -0.2439(2) -0.7023(2) -0.08828(16) 0.0315(4) Uani 1 1 d . . .
H22 H -0.175(2) -0.7083(19) -0.1347(16) 0.034(5) Uiso 1 1 d . . .
C23 C -0.3531(3) -0.8203(2) -0.06878(16) 0.0346(4) Uani 1 1 d . . .
H23 H -0.365(3) -0.912(2) -0.1016(18) 0.043(6) Uiso 1 1 d . . .
C24 C -0.4469(2) -0.81264(19) 0.00086(15) 0.0300(4) Uani 1 1 d . . .
H24 H -0.523(2) -0.894(2) 0.0131(16) 0.030(5) 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'
N N 0.0061 0.0033 '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'
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
F3 B1 F2 110.69(15) . . ?
F3 B1 F4 108.70(15) . . ?
F2 B1 F4 110.20(15) . . ?
F3 B1 F1 109.43(15) . . ?
F2 B1 F1 109.09(14) . . ?
F4 B1 F1 108.70(14) . . ?
C6 N1 C7 110.71(12) . . ?
C6 N1 C11 112.63(12) . . ?
C7 N1 C11 112.16(12) . . ?
C6 N1 H1N 105.0(12) . . ?
C7 N1 H1N 106.5(12) . . ?
C11 N1 H1N 109.4(12) . . ?
C8 N2 C9 113.06(13) . . ?
C8 N2 C18 112.14(12) . . ?
C9 N2 C18 110.88(12) . . ?
C10 C1 C2 177.26(17) 2_446 . ?
C3 C2 C1 124.67(15) . . ?
C3 C2 H2 117.6(11) . . ?
C1 C2 H2 117.7(10) . . ?
C2 C3 C4 124.27(16) . . ?
C2 C3 H3 121.4(11) . . ?
C4 C3 H3 114.4(11) . . ?
C5 C4 C3 175.92(18) . . ?
C4 C5 C6 175.49(17) . . ?
C5 C6 N1 112.22(13) . . ?
C5 C6 H6A 111.3(10) . . ?
N1 C6 H6A 107.9(10) . . ?
C5 C6 H6B 111.2(10) . . ?
N1 C6 H6B 105.0(10) . . ?
H6A C6 H6B 109.0(14) . . ?
N1 C7 C8 111.43(13) . . ?
N1 C7 H7A 107.4(10) . . ?
C8 C7 H7A 110.3(10) . . ?
N1 C7 H7B 104.1(10) . . ?
C8 C7 H7B 113.6(10) . . ?
H7A C7 H7B 109.7(14) . . ?
N2 C8 C7 110.59(13) . . ?
N2 C8 H8A 113.4(10) . . ?
C7 C8 H8A 108.2(10) . . ?
N2 C8 H8B 108.5(10) . . ?
C7 C8 H8B 110.8(10) . . ?
H8A C8 H8B 105.3(14) . . ?
C10 C9 N2 114.02(13) . . ?
C10 C9 H9A 110.8(10) . . ?
N2 C9 H9A 106.7(10) . . ?
C10 C9 H9B 109.2(10) . . ?
N2 C9 H9B 109.7(10) . . ?
H9A C9 H9B 106.1(14) . . ?
C1 C10 C9 177.52(18) 2_446 . ?
C12 C11 N1 113.83(13) . . ?
C12 C11 H11A 109.5(10) . . ?
N1 C11 H11A 105.8(10) . . ?
C12 C11 H11B 110.7(11) . . ?
N1 C11 H11B 106.4(11) . . ?
H11A C11 H11B 110.4(15) . . ?
C17 C12 C13 118.76(15) . . ?
C17 C12 C11 121.58(14) . . ?
C13 C12 C11 119.58(15) . . ?
C14 C13 C12 120.70(17) . . ?
C14 C13 H13 122.1(12) . . ?
C12 C13 H13 117.2(12) . . ?
C15 C14 C13 119.79(17) . . ?
C15 C14 H14 118.9(13) . . ?
C13 C14 H14 121.2(13) . . ?
C14 C15 C16 120.21(17) . . ?
C14 C15 H15 119.4(13) . . ?
C16 C15 H15 120.4(13) . . ?
C15 C16 C17 120.08(17) . . ?
C15 C16 H16 121.9(13) . . ?
C17 C16 H16 118.0(13) . . ?
C16 C17 C12 120.45(16) . . ?
C16 C17 H17 118.8(11) . . ?
C12 C17 H17 120.7(11) . . ?
N2 C18 C19 111.15(13) . . ?
N2 C18 H18A 107.8(10) . . ?
C19 C18 H18A 107.5(10) . . ?
N2 C18 H18B 112.7(10) . . ?
C19 C18 H18B 109.6(10) . . ?
H18A C18 H18B 107.9(14) . . ?
C24 C19 C20 118.47(16) . . ?
C24 C19 C18 121.62(15) . . ?
C20 C19 C18 119.91(14) . . ?
C21 C20 C19 121.14(16) . . ?
C21 C20 H20 120.0(10) . . ?
C19 C20 H20 118.8(10) . . ?
C22 C21 C20 119.63(17) . . ?
C22 C21 H21 118.2(13) . . ?
C20 C21 H21 122.1(13) . . ?
C23 C22 C21 119.95(17) . . ?
C23 C22 H22 119.9(11) . . ?
C21 C22 H22 120.1(11) . . ?
C22 C23 C24 120.34(17) . . ?
C22 C23 H23 121.3(12) . . ?
C24 C23 H23 118.3(12) . . ?
C19 C24 C23 120.49(17) . . ?
C19 C24 H24 119.2(12) . . ?
C23 C24 H24 120.3(12) . . ?
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 F3 1.375(2) . ?
B1 F2 1.382(2) . ?
B1 F4 1.383(2) . ?
B1 F1 1.402(2) . ?
N1 C6 1.510(2) . ?
N1 C7 1.512(2) . ?
N1 C11 1.512(2) . ?
N1 H1N 0.93(2) . ?
N2 C8 1.464(2) . ?
N2 C9 1.476(2) . ?
N2 C18 1.476(2) . ?
C1 C10 1.199(2) 2_446 ?
C1 C2 1.423(2) . ?
C2 C3 1.336(2) . ?
C2 H2 0.964(17) . ?
C3 C4 1.424(2) . ?
C3 H3 0.953(19) . ?
C4 C5 1.197(2) . ?
C5 C6 1.458(2) . ?
C6 H6A 0.999(18) . ?
C6 H6B 0.975(18) . ?
C7 C8 1.521(2) . ?
C7 H7A 0.947(17) . ?
C7 H7B 0.977(17) . ?
C8 H8A 0.978(18) . ?
C8 H8B 0.971(18) . ?
C9 C10 1.474(2) . ?
C9 H9A 1.027(18) . ?
C9 H9B 1.001(18) . ?
C10 C1 1.199(2) 2_446 ?
C11 C12 1.506(2) . ?
C11 H11A 0.976(18) . ?
C11 H11B 0.941(18) . ?
C12 C17 1.391(2) . ?
C12 C13 1.398(2) . ?
C13 C14 1.385(3) . ?
C13 H13 0.96(2) . ?
C14 C15 1.382(3) . ?
C14 H14 0.97(2) . ?
C15 C16 1.383(3) . ?
C15 H15 0.93(2) . ?
C16 C17 1.388(2) . ?
C16 H16 1.01(2) . ?
C17 H17 0.985(19) . ?
C18 C19 1.509(2) . ?
C18 H18A 1.002(18) . ?
C18 H18B 0.992(18) . ?
C19 C24 1.386(2) . ?
C19 C20 1.393(2) . ?
C20 C21 1.388(2) . ?
C20 H20 0.993(18) . ?
C21 C22 1.385(3) . ?
C21 H21 0.98(2) . ?
C22 C23 1.376(3) . ?
C22 H22 0.98(2) . ?
C23 C24 1.394(3) . ?
C23 H23 0.99(2) . ?
C24 H24 0.945(19) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N F1 0.93(2) 1.99(2) 2.8413(16) 151.5(17) 2_556
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
C10 C1 C2 C3 -147(4) 2_446 . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 -169(2) . . . . ?
C3 C4 C5 C6 21(4) . . . . ?
C4 C5 C6 N1 -148(2) . . . . ?
C7 N1 C6 C5 -69.29(17) . . . . ?
C11 N1 C6 C5 57.19(18) . . . . ?
C6 N1 C7 C8 -171.31(13) . . . . ?
C11 N1 C7 C8 61.96(16) . . . . ?
C9 N2 C8 C7 71.15(16) . . . . ?
C18 N2 C8 C7 -162.60(13) . . . . ?
N1 C7 C8 N2 42.97(17) . . . . ?
C8 N2 C9 C10 67.25(17) . . . . ?
C18 N2 C9 C10 -59.66(17) . . . . ?
N2 C9 C10 C1 24(4) . . . 2_446 ?
C6 N1 C11 C12 49.21(18) . . . . ?
C7 N1 C11 C12 174.91(13) . . . . ?
N1 C11 C12 C17 69.6(2) . . . . ?
N1 C11 C12 C13 -113.72(17) . . . . ?
C17 C12 C13 C14 0.8(3) . . . . ?
C11 C12 C13 C14 -175.97(16) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C15 C16 C17 C12 -0.1(3) . . . . ?
C13 C12 C17 C16 -0.6(3) . . . . ?
C11 C12 C17 C16 176.11(16) . . . . ?
C8 N2 C18 C19 164.01(13) . . . . ?
C9 N2 C18 C19 -68.57(16) . . . . ?
N2 C18 C19 C24 125.04(17) . . . . ?
N2 C18 C19 C20 -55.2(2) . . . . ?
C24 C19 C20 C21 0.3(3) . . . . ?
C18 C19 C20 C21 -179.49(16) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C20 C19 C24 C23 0.0(3) . . . . ?
C18 C19 C24 C23 179.75(17) . . . . ?
C22 C23 C24 C19 0.0(3) . . . . ?
