#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/36/7103655.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_7103655
loop_
_publ_author_name
'Bhattacharyya, Sibaprasad'
'Clark, Aurora E.'
'Pink, Maren'
'Zaleski, Jeffrey M.'
_publ_section_title
;
 Isolation of electronic from geometric contributions to Bergman
 cyclization of metalloenediynes
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   10
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1156
_journal_page_last               1157
_journal_paper_doi               10.1039/b301690k
_journal_year                    2003
_chemical_formula_moiety         'C24 H26 N2'
_chemical_formula_sum            'C24 H26 N2'
_chemical_formula_weight         342.47
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.9460(10)
_cell_angle_beta                 79.7450(10)
_cell_angle_gamma                79.4360(10)
_cell_formula_units_Z            2
_cell_length_a                   5.6575(2)
_cell_length_b                   11.4775(4)
_cell_length_c                   14.8070(6)
_cell_measurement_reflns_used    5484
_cell_measurement_temperature    137(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.15
_cell_volume                     926.03(6)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'XTEL (local library)'
_computing_publication_material  'XCIF (Bruker, 1999), XTEL (local library)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Alatomare et al., 1993)'
_diffrn_ambient_temperature      137(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 44.52
_diffrn_detector_type            'Bruker SMART 6000'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
'0.30 degree frames measured for 10 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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20665
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  606
_diffrn_standards_number         140
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_correction_T_min  0.9858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0445
_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 w=1/[σ²(Fo²)+(0.0532P)²+0.4285P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                3564
_reflns_number_total             4258
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b301690k.txt
_cod_data_source_block           03007
_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               7103655
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
N1 N 0.0683(2) -0.33063(10) 0.89664(8) 0.0251(2) Uani 1 1 d . . .
N2 N 0.1579(2) -0.16661(9) 0.67893(8) 0.0228(2) Uani 1 1 d . . .
C1 C 0.0747(3) -0.42853(12) 0.84042(10) 0.0271(3) Uani 1 1 d . . .
H1A H -0.0744 -0.4120 0.8115 0.033(4) Uiso 1 1 calc R . .
H1B H 0.0670 -0.5024 0.8823 0.033(4) Uiso 1 1 calc R . .
C2 C 0.2934(2) -0.45242(11) 0.76453(9) 0.0226(3) Uani 1 1 d . . .
C3 C 0.4886(3) -0.54107(12) 0.78215(9) 0.0258(3) Uani 1 1 d . . .
H3A H 0.4797 -0.5865 0.8404 0.032(4) Uiso 1 1 calc R . .
C4 C 0.6958(3) -0.56452(12) 0.71654(10) 0.0278(3) Uani 1 1 d . . .
H4A H 0.8288 -0.6235 0.7306 0.032(4) Uiso 1 1 calc R . .
C5 C 0.7065(3) -0.50123(12) 0.63057(10) 0.0300(3) Uani 1 1 d . . .
H5A H 0.8463 -0.5173 0.5849 0.040(5) Uiso 1 1 calc R . .
C6 C 0.5121(3) -0.41416(12) 0.61126(10) 0.0277(3) Uani 1 1 d . . .
H6A H 0.5193 -0.3721 0.5517 0.037(5) Uiso 1 1 calc R . .
C7 C 0.3065(2) -0.38705(11) 0.67743(9) 0.0228(3) Uani 1 1 d . . .
C8 C 0.1119(2) -0.28207(12) 0.65720(10) 0.0258(3) Uani 1 1 d . . .
H8A H 0.0979 -0.2762 0.5910 0.024(4) Uiso 1 1 calc R . .
H8B H -0.0462 -0.2974 0.6931 0.027(4) Uiso 1 1 calc R . .
C9 C 0.0189(2) -0.21096(12) 0.85019(9) 0.0248(3) Uani 1 1 d . . .
H9A H -0.0152 -0.1537 0.8976 0.026(4) Uiso 1 1 calc R . .
H9B H -0.1320 -0.2047 0.8235 0.030(4) Uiso 1 1 calc R . .
C10 C 0.2163(2) -0.17075(12) 0.77336(9) 0.0236(3) Uani 1 1 d . . .
H10A H 0.2412 -0.0906 0.7837 0.025(4) Uiso 1 1 calc R . .
H10B H 0.3714 -0.2259 0.7775 0.019(3) Uiso 1 1 calc R . .
C11 C 0.2726(2) -0.35171(12) 0.94811(9) 0.0254(3) Uani 1 1 d . . .
H11A H 0.4257 -0.3475 0.9044 0.031(4) Uiso 1 1 calc R . .
H11B H 0.2847 -0.4329 0.9805 0.035(4) Uiso 1 1 calc R . .
C12 C 0.2447(2) -0.26227(12) 1.01780(9) 0.0230(3) Uani 1 1 d . . .
C13 C 0.4283(3) -0.19700(14) 1.01866(10) 0.0321(3) Uani 1 1 d . . .
H13A H 0.5725 -0.2080 0.9744 0.036(5) Uiso 1 1 calc R . .
C14 C 0.4034(3) -0.11556(15) 1.08364(12) 0.0372(4) Uani 1 1 d . . .
H14A H 0.5307 -0.0718 1.0835 0.051(6) Uiso 1 1 calc R . .
C15 C 0.1950(3) -0.09824(13) 1.14807(10) 0.0322(3) Uani 1 1 d . . .
H15A H 0.1783 -0.0428 1.1923 0.038(5) Uiso 1 1 calc R . .
C16 C 0.0100(3) -0.16228(13) 1.14782(10) 0.0303(3) Uani 1 1 d . . .
H16A H -0.1342 -0.1506 1.1920 0.043(5) Uiso 1 1 calc R . .
C17 C 0.0351(2) -0.24354(12) 1.08310(9) 0.0260(3) Uani 1 1 d . . .
H17A H -0.0928 -0.2870 1.0834 0.030(4) Uiso 1 1 calc R . .
C18 C 0.3556(2) -0.12286(11) 0.61183(9) 0.0213(3) Uani 1 1 d . . .
H18A H 0.3385 -0.1373 0.5489 0.024(4) Uiso 1 1 calc R . .
H18B H 0.5146 -0.1675 0.6252 0.021(4) Uiso 1 1 calc R . .
C19 C 0.3501(2) 0.00857(11) 0.61569(8) 0.0191(2) Uani 1 1 d . . .
C20 C 0.1622(2) 0.09161(11) 0.58449(9) 0.0220(3) Uani 1 1 d . . .
H20A H 0.0387 0.0650 0.5604 0.028(4) Uiso 1 1 calc R . .
C21 C 0.1536(2) 0.21265(12) 0.58815(9) 0.0236(3) Uani 1 1 d . . .
H21A H 0.0250 0.2681 0.5663 0.028(4) Uiso 1 1 calc R . .
C22 C 0.3324(2) 0.25302(11) 0.62365(9) 0.0229(3) Uani 1 1 d . . .
H22A H 0.3252 0.3357 0.6270 0.030(4) Uiso 1 1 calc R . .
C23 C 0.5212(2) 0.17136(12) 0.65402(9) 0.0242(3) Uani 1 1 d . . .
H23A H 0.6449 0.1983 0.6778 0.030(4) Uiso 1 1 calc R . .
C24 C 0.5302(2) 0.04986(11) 0.64986(9) 0.0225(3) Uani 1 1 d . . .
H24A H 0.6607 -0.0054 0.6706 0.025(4) Uiso 1 1 calc R . .
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'
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
C9 N1 C11 115.12(11) . . ?
C9 N1 C1 115.44(11) . . ?
C11 N1 C1 112.05(11) . . ?
C18 N2 C8 111.73(10) . . ?
C18 N2 C10 108.89(10) . . ?
C8 N2 C10 113.03(10) . . ?
N1 C1 C2 117.18(11) . . ?
N1 C1 H1A 108.0 . . ?
C2 C1 H1A 108.0 . . ?
N1 C1 H1B 108.0 . . ?
C2 C1 H1B 108.0 . . ?
H1A C1 H1B 107.2 . . ?
C3 C2 C7 118.74(12) . . ?
C3 C2 C1 119.07(12) . . ?
C7 C2 C1 122.19(12) . . ?
C4 C3 C2 121.64(12) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?
C5 C4 C3 119.41(13) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
C4 C5 C6 119.72(13) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C5 C6 C7 121.45(13) . . ?
C5 C6 H6A 119.3 . . ?
C7 C6 H6A 119.3 . . ?
C6 C7 C2 118.99(12) . . ?
C6 C7 C8 119.65(12) . . ?
C2 C7 C8 121.17(12) . . ?
N2 C8 C7 114.41(11) . . ?
N2 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
N2 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N1 C9 C10 117.89(11) . . ?
N1 C9 H9A 107.8 . . ?
C10 C9 H9A 107.8 . . ?
N1 C9 H9B 107.8 . . ?
C10 C9 H9B 107.8 . . ?
H9A C9 H9B 107.2 . . ?
N2 C10 C9 113.96(11) . . ?
N2 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
N2 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N1 C11 C12 112.22(11) . . ?
N1 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C17 118.23(13) . . ?
C13 C12 C11 120.89(12) . . ?
C17 C12 C11 120.88(12) . . ?
C12 C13 C14 120.80(14) . . ?
C12 C13 H13A 119.6 . . ?
C14 C13 H13A 119.6 . . ?
C15 C14 C13 120.31(14) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C16 119.55(14) . . ?
C14 C15 H15A 120.2 . . ?
C16 C15 H15A 120.2 . . ?
C15 C16 C17 120.11(14) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C16 C17 C12 121.00(13) . . ?
C16 C17 H17A 119.5 . . ?
C12 C17 H17A 119.5 . . ?
N2 C18 C19 111.26(10) . . ?
N2 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
N2 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C24 C19 C20 118.49(12) . . ?
C24 C19 C18 121.39(11) . . ?
C20 C19 C18 120.12(11) . . ?
C21 C20 C19 120.84(12) . . ?
C21 C20 H20A 119.6 . . ?
C19 C20 H20A 119.6 . . ?
C20 C21 C22 120.28(12) . . ?
C20 C21 H21A 119.9 . . ?
C22 C21 H21A 119.9 . . ?
C23 C22 C21 119.35(12) . . ?
C23 C22 H22A 120.3 . . ?
C21 C22 H22A 120.3 . . ?
C22 C23 C24 120.28(12) . . ?
C22 C23 H23A 119.9 . . ?
C24 C23 H23A 119.9 . . ?
C19 C24 C23 120.75(12) . . ?
C19 C24 H24A 119.6 . . ?
C23 C24 H24A 119.6 . . ?
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
N1 C9 1.4606(17) . ?
N1 C11 1.4629(18) . ?
N1 C1 1.4701(17) . ?
N2 C18 1.4760(16) . ?
N2 C8 1.4792(17) . ?
N2 C10 1.4864(17) . ?
C1 C2 1.5248(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.3960(18) . ?
C2 C7 1.4073(18) . ?
C3 C4 1.390(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.383(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.3950(19) . ?
C6 H6A 0.9500 . ?
C7 C8 1.5152(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5371(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5121(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.390(2) . ?
C12 C17 1.3918(18) . ?
C13 C14 1.394(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.379(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.386(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.390(2) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 C19 1.5110(17) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C24 1.3921(18) . ?
C19 C20 1.3953(17) . ?
C20 C21 1.3885(18) . ?
C20 H20A 0.9500 . ?
C21 C22 1.3913(19) . ?
C21 H21A 0.9500 . ?
C22 C23 1.3861(19) . ?
C22 H22A 0.9500 . ?
C23 C24 1.3946(18) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
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
C9 N1 C1 C2 72.07(15) . . . . ?
C11 N1 C1 C2 -62.35(15) . . . . ?
N1 C1 C2 C3 96.55(15) . . . . ?
N1 C1 C2 C7 -82.68(16) . . . . ?
C7 C2 C3 C4 1.12(19) . . . . ?
C1 C2 C3 C4 -178.13(12) . . . . ?
C2 C3 C4 C5 -2.1(2) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C4 C5 C6 C7 1.3(2) . . . . ?
C5 C6 C7 C2 -2.2(2) . . . . ?
C5 C6 C7 C8 172.94(12) . . . . ?
C3 C2 C7 C6 0.97(18) . . . . ?
C1 C2 C7 C6 -179.80(12) . . . . ?
C3 C2 C7 C8 -174.06(12) . . . . ?
C1 C2 C7 C8 5.17(19) . . . . ?
C18 N2 C8 C7 72.91(14) . . . . ?
C10 N2 C8 C7 -50.34(15) . . . . ?
C6 C7 C8 N2 -86.00(15) . . . . ?
C2 C7 C8 N2 89.00(15) . . . . ?
C11 N1 C9 C10 63.55(15) . . . . ?
C1 N1 C9 C10 -69.47(15) . . . . ?
C18 N2 C10 C9 177.97(10) . . . . ?
C8 N2 C10 C9 -57.23(14) . . . . ?
N1 C9 C10 N2 106.29(13) . . . . ?
C9 N1 C11 C12 55.00(15) . . . . ?
C1 N1 C11 C12 -170.42(11) . . . . ?
N1 C11 C12 C13 -126.43(13) . . . . ?
N1 C11 C12 C17 53.89(16) . . . . ?
C17 C12 C13 C14 0.4(2) . . . . ?
C11 C12 C13 C14 -179.27(13) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 C12 0.1(2) . . . . ?
C13 C12 C17 C16 -0.3(2) . . . . ?
C11 C12 C17 C16 179.34(12) . . . . ?
C8 N2 C18 C19 162.31(10) . . . . ?
C10 N2 C18 C19 -72.13(13) . . . . ?
N2 C18 C19 C24 110.48(13) . . . . ?
N2 C18 C19 C20 -69.65(15) . . . . ?
C24 C19 C20 C21 -0.57(18) . . . . ?
C18 C19 C20 C21 179.56(11) . . . . ?
C19 C20 C21 C22 -0.36(19) . . . . ?
C20 C21 C22 C23 0.97(19) . . . . ?
C21 C22 C23 C24 -0.65(19) . . . . ?
C20 C19 C24 C23 0.89(18) . . . . ?
C18 C19 C24 C23 -179.24(11) . . . . ?
C22 C23 C24 C19 -0.29(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21150875
2 PubChem 85900215
