#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557928.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_1557928
loop_
_publ_author_name
'Curbet, Idriss'
'Colombel-Rouen, Sophie'
'Manguin, Romane'
'Clermont, Anthony'
'Quelhas, Alexandre'
'Müller, Daniel S.'
'Roisnel, Thierry'
'Baslé, Olivier'
'Trolez, Yann'
'Mauduit, Marc'
_publ_section_title
;
 Expedient synthesis of conjugated triynes via alkyne metathesis
;
_journal_issue                   19
_journal_name_full               'Chemical Science'
_journal_page_first              4934
_journal_page_last               4938
_journal_paper_doi               10.1039/D0SC01124J
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C24 H18'
_chemical_formula_sum            'C24 H18'
_chemical_formula_weight         306.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2019-04-04 deposited with the CCDC.	2020-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3055(16)
_cell_length_b                   10.3538(15)
_cell_length_c                   18.151(3)
_cell_measurement_reflns_used    7576
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.26
_cell_measurement_wavelength     0.71073
_cell_volume                     1748.8(5)
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10436
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         2.943
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.580
_exptl_crystal_size_min          0.450
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0359
_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)+(0.0480P)²+0.2511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3603
_reflns_number_total             3996
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0sc01124j2.cif
_cod_data_source_block           RMA43
_cod_depositor_comments
;
 Adding full bibliography for 1557923--1557928.cif.

2022-06-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C16 H12'
_cod_original_formula_sum        'C16 H12'
_cod_original_formula_units_Z    6
_cod_original_formula_weight     204.26
_cod_database_code               1557928
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C1 C 1.0209(2) 0.0869(2) 0.75934(12) 0.0373(5) Uani 1 1 d . . . . .
H1A H 1.110662 0.072165 0.732417 0.056 Uiso 1 1 calc R U . . .
H1B H 0.970751 0.004518 0.766175 0.056 Uiso 1 1 calc R U . . .
H1C H 1.042404 0.124855 0.807554 0.056 Uiso 1 1 calc R U . . .
C2 C 0.9298(2) 0.17493(19) 0.71751(11) 0.0294(4) Uani 1 1 d . . . . .
C3 C 0.8562(2) 0.24965(18) 0.68427(10) 0.0278(4) Uani 1 1 d . . . . .
C4 C 0.77443(19) 0.34045(17) 0.64753(10) 0.0262(4) Uani 1 1 d . . . . .
C5 C 0.70498(18) 0.42136(17) 0.61652(10) 0.0249(4) Uani 1 1 d . . . . .
C6 C 0.62096(17) 0.52568(16) 0.58096(9) 0.0212(3) Uani 1 1 d . . . . .
C7 C 0.63806(18) 0.64527(17) 0.63134(10) 0.0241(4) Uani 1 1 d . . . . .
C8 C 0.70816(19) 0.75657(18) 0.60925(11) 0.0292(4) Uani 1 1 d . . . . .
H8 H 0.742450 0.763986 0.560130 0.035 Uiso 1 1 calc R U . . .
C9 C 0.7288(2) 0.8582(2) 0.65888(13) 0.0385(5) Uani 1 1 d . . . . .
H9 H 0.777875 0.933924 0.643453 0.046 Uiso 1 1 calc R U . . .
C10 C 0.6782(2) 0.8491(2) 0.73001(13) 0.0430(5) Uani 1 1 d . . . . .
H10 H 0.692972 0.918136 0.763623 0.052 Uiso 1 1 calc R U . . .
C11 C 0.6058(2) 0.7388(2) 0.75248(13) 0.0441(5) Uani 1 1 d . . . . .
H11 H 0.569461 0.732798 0.801272 0.053 Uiso 1 1 calc R U . . .
C12 C 0.5865(2) 0.6375(2) 0.70378(11) 0.0337(4) Uani 1 1 d . . . . .
H12 H 0.537727 0.561780 0.719591 0.040 Uiso 1 1 calc R U . . .
C13 C 0.68073(18) 0.55178(15) 0.50312(10) 0.0228(4) Uani 1 1 d . . . . .
C14 C 0.8249(2) 0.53004(19) 0.48752(12) 0.0320(4) Uani 1 1 d . . . . .
H14 H 0.886948 0.498910 0.525097 0.038 Uiso 1 1 calc R U . . .
C15 C 0.8792(2) 0.5534(2) 0.41738(14) 0.0417(5) Uani 1 1 d . . . . .
H15 H 0.977443 0.536347 0.407089 0.050 Uiso 1 1 calc R U . . .
C16 C 0.7912(3) 0.6012(2) 0.36275(12) 0.0416(5) Uani 1 1 d . . . . .
H16 H 0.828490 0.616997 0.314863 0.050 Uiso 1 1 calc R U . . .
C17 C 0.6488(3) 0.6260(2) 0.37806(11) 0.0401(5) Uani 1 1 d . . . . .
H17 H 0.588136 0.660369 0.340831 0.048 Uiso 1 1 calc R U . . .
C18 C 0.5938(2) 0.60084(19) 0.44764(10) 0.0318(4) Uani 1 1 d . . . . .
H18 H 0.495203 0.617440 0.457447 0.038 Uiso 1 1 calc R U . . .
C19 C 0.46271(18) 0.48152(16) 0.57502(9) 0.0217(3) Uani 1 1 d . . . . .
C20 C 0.35000(19) 0.56905(18) 0.58133(11) 0.0271(4) Uani 1 1 d . . . . .
H20 H 0.369747 0.657331 0.591366 0.033 Uiso 1 1 calc R U . . .
C21 C 0.2086(2) 0.52814(18) 0.57304(12) 0.0330(4) Uani 1 1 d . . . . .
H21 H 0.132502 0.588908 0.576857 0.040 Uiso 1 1 calc R U . . .
C22 C 0.1780(2) 0.4001(2) 0.55933(13) 0.0372(5) Uani 1 1 d . . . . .
H22 H 0.081184 0.372032 0.555046 0.045 Uiso 1 1 calc R U . . .
C23 C 0.2895(2) 0.31286(18) 0.55188(12) 0.0366(5) Uani 1 1 d . . . . .
H23 H 0.269181 0.224731 0.541685 0.044 Uiso 1 1 calc R U . . .
C24 C 0.4311(2) 0.35331(18) 0.55920(10) 0.0278(4) Uani 1 1 d . . . . .
H24 H 0.506974 0.292807 0.553345 0.033 Uiso 1 1 calc R U . . .
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'
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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 178.4(2) . . ?
C2 C3 C4 177.4(2) . . ?
C5 C4 C3 178.5(2) . . ?
C4 C5 C6 177.31(19) . . ?
C5 C6 C13 109.67(14) . . ?
C5 C6 C19 108.52(14) . . ?
C13 C6 C19 109.36(14) . . ?
C5 C6 C7 105.77(14) . . ?
C13 C6 C7 111.35(14) . . ?
C19 C6 C7 112.08(14) . . ?
C8 C7 C12 118.77(17) . . ?
C8 C7 C6 122.93(16) . . ?
C12 C7 C6 118.22(17) . . ?
C7 C8 C9 120.29(19) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.9(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C18 C13 C14 118.32(18) . . ?
C18 C13 C6 121.23(15) . . ?
C14 C13 C6 120.43(16) . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.5(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.90(19) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C24 C19 C20 118.66(16) . . ?
C24 C19 C6 119.92(15) . . ?
C20 C19 C6 121.33(15) . . ?
C21 C20 C19 120.41(17) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 120.52(18) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.41(18) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C22 C23 C24 120.37(17) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 120.59(17) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
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
C1 C2 1.458(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.196(3) . ?
C3 C4 1.381(2) . ?
C4 C5 1.199(2) . ?
C5 C6 1.481(2) . ?
C6 C13 1.542(2) . ?
C6 C19 1.546(2) . ?
C6 C7 1.548(2) . ?
C7 C8 1.384(3) . ?
C7 C12 1.402(3) . ?
C8 C9 1.398(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.388(3) . ?
C13 C14 1.389(2) . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.390(2) . ?
C19 C20 1.391(2) . ?
C20 C21 1.390(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(3) . ?
C23 H23 0.9500 . ?
C24 H24 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
C5 C6 C7 C8 114.66(18) . . . . ?
C13 C6 C7 C8 -4.4(2) . . . . ?
C19 C6 C7 C8 -127.26(17) . . . . ?
C5 C6 C7 C12 -61.98(19) . . . . ?
C13 C6 C7 C12 178.95(15) . . . . ?
C19 C6 C7 C12 56.1(2) . . . . ?
C12 C7 C8 C9 1.0(3) . . . . ?
C6 C7 C8 C9 -175.64(16) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C10 C11 C12 C7 -0.7(3) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
C6 C7 C12 C11 176.47(17) . . . . ?
C5 C6 C13 C18 152.78(16) . . . . ?
C19 C6 C13 C18 33.9(2) . . . . ?
C7 C6 C13 C18 -90.51(18) . . . . ?
C5 C6 C13 C14 -29.1(2) . . . . ?
C19 C6 C13 C14 -147.99(16) . . . . ?
C7 C6 C13 C14 87.61(19) . . . . ?
C18 C13 C14 C15 -1.9(3) . . . . ?
C6 C13 C14 C15 179.98(16) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C16 C17 C18 C13 0.6(3) . . . . ?
C14 C13 C18 C17 0.8(3) . . . . ?
C6 C13 C18 C17 178.99(18) . . . . ?
C5 C6 C19 C24 -37.4(2) . . . . ?
C13 C6 C19 C24 82.22(19) . . . . ?
C7 C6 C19 C24 -153.81(16) . . . . ?
C5 C6 C19 C20 146.07(16) . . . . ?
C13 C6 C19 C20 -94.34(19) . . . . ?
C7 C6 C19 C20 29.6(2) . . . . ?
C24 C19 C20 C21 1.0(3) . . . . ?
C6 C19 C20 C21 177.56(18) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
C20 C21 C22 C23 -1.7(3) . . . . ?
C21 C22 C23 C24 1.0(3) . . . . ?
C22 C23 C24 C19 0.8(3) . . . . ?
C20 C19 C24 C23 -1.8(3) . . . . ?
C6 C19 C24 C23 -178.40(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306345
