#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:34:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180268 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/54/7115447.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_7115447
loop_
_publ_author_name
'Kyle D. Reichl'
'Alexander T. Radosevich'
_publ_section_title
;
 A phosphine-mediated stereocontrolled synthesis of Z-enediynes by a
 vicinal dialkynylation of ethynylphosphonium salts
;
_journal_name_full               Chem.Commun.
_journal_page_first              9302
_journal_paper_doi               10.1039/C4cc03415E
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C24 H16'
_chemical_formula_sum            'C24 H16'
_chemical_formula_weight         304.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.56(3)
_cell_length_b                   17.03(3)
_cell_length_c                   5.895(10)
_cell_measurement_reflns_used    1029
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.953
_cell_measurement_theta_min      2.390
_cell_volume                     1763(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9843
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_correction_T_min  0.9884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.095
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3880
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1694
_refine_ls_R_factor_gt           0.0673
_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)+(0.1023P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1723
_refine_ls_wR_factor_ref         0.2241
_reflns_number_gt                1607
_reflns_number_total             3880
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc03415e2.cif
_cod_data_source_block           kor1o
_cod_original_cell_volume        1762(5)
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7115447
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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
C1 C 0.3869(2) 0.1222(2) 0.2409(8) 0.0918(12) Uani 1 1 d .
C2 C 0.3738(2) 0.0496(2) 0.3728(8) 0.0835(11) Uani 1 1 d .
C3 C 0.4108(2) 0.0362(3) 0.5755(9) 0.1037(14) Uani 1 1 d .
H3 H 0.4438 0.0743 0.6315 0.124 Uiso 1 1 calc R
C4 C 0.4005(3) -0.0314(3) 0.6964(10) 0.1156(15) Uani 1 1 d .
H4 H 0.4269 -0.0394 0.8312 0.139 Uiso 1 1 calc R
C5 C 0.3522(3) -0.0860(3) 0.6199(12) 0.1180(17) Uani 1 1 d .
H5 H 0.3451 -0.1316 0.7036 0.142 Uiso 1 1 calc R
C6 C 0.3136(3) -0.0763(3) 0.4235(11) 0.1117(15) Uani 1 1 d .
H6 H 0.2802 -0.1150 0.3733 0.134 Uiso 1 1 calc R
C7 C 0.3237(2) -0.0098(3) 0.2998(9) 0.1029(13) Uani 1 1 d .
H7 H 0.2971 -0.0034 0.1646 0.124 Uiso 1 1 calc R
C8 C 0.4489(2) 0.1739(2) 0.3165(8) 0.0935(11) Uani 1 1 d .
C9 C 0.5004(2) 0.2140(2) 0.3793(9) 0.0954(12) Uani 1 1 d .
C10 C 0.56062(19) 0.2611(2) 0.4522(8) 0.0855(11) Uani 1 1 d .
C11 C 0.5962(3) 0.2470(2) 0.6605(9) 0.1128(15) Uani 1 1 d .
H11 H 0.5770 0.2091 0.7587 0.135 Uiso 1 1 calc R
C12 C 0.6596(3) 0.2895(3) 0.7183(10) 0.1216(16) Uani 1 1 d .
H12 H 0.6845 0.2790 0.8542 0.146 Uiso 1 1 calc R
C13 C 0.6860(3) 0.3459(3) 0.5817(12) 0.1186(16) Uani 1 1 d .
H13 H 0.7285 0.3750 0.6240 0.142 Uiso 1 1 calc R
C14 C 0.6521(3) 0.3603(3) 0.3887(12) 0.142(2) Uani 1 1 d .
H14 H 0.6710 0.3998 0.2956 0.171 Uiso 1 1 calc R
C15 C 0.5904(3) 0.3193(3) 0.3209(10) 0.1298(17) Uani 1 1 d .
H15 H 0.5678 0.3310 0.1822 0.156 Uiso 1 1 calc R
C16 C 0.3470(2) 0.1453(3) 0.0596(8) 0.1036(14) Uani 1 1 d .
H16 H 0.3081 0.1119 0.0141 0.124 Uiso 1 1 calc R
C17 C 0.3564(2) 0.2139(3) -0.0718(10) 0.1018(13) Uani 1 1 d .
C18 C 0.3668(3) 0.2697(3) -0.1807(8) 0.1042(14) Uani 1 1 d .
C19 C 0.3757(2) 0.3399(3) -0.3115(8) 0.0925(12) Uani 1 1 d .
C20 C 0.4229(2) 0.3991(3) -0.2451(9) 0.1115(14) Uani 1 1 d .
H20 H 0.4503 0.3937 -0.1110 0.134 Uiso 1 1 calc R
C21 C 0.4311(3) 0.4654(3) -0.3689(14) 0.1410(19) Uani 1 1 d .
H21 H 0.4640 0.5045 -0.3186 0.169 Uiso 1 1 calc R
C22 C 0.3924(3) 0.4757(3) -0.5634(12) 0.1273(18) Uani 1 1 d .
H22 H 0.3974 0.5219 -0.6463 0.153 Uiso 1 1 calc R
C23 C 0.3453(3) 0.4166(4) -0.6368(10) 0.1334(19) Uani 1 1 d .
H23 H 0.3185 0.4224 -0.7719 0.160 Uiso 1 1 calc R
C24 C 0.3374(3) 0.3492(3) -0.5134(9) 0.1187(15) Uani 1 1 d .
H24 H 0.3058 0.3093 -0.5662 0.142 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C16 C1 C8 116.9(4)
C16 C1 C2 125.9(4)
C8 C1 C2 117.2(4)
C3 C2 C7 116.1(4)
C3 C2 C1 121.4(4)
C7 C2 C1 122.5(4)
C4 C3 C2 122.0(4)
C4 C3 H3 119.0
C2 C3 H3 119.0
C5 C4 C3 119.6(5)
C5 C4 H4 120.2
C3 C4 H4 120.2
C4 C5 C6 121.5(5)
C4 C5 H5 119.2
C6 C5 H5 119.2
C5 C6 C7 119.7(5)
C5 C6 H6 120.2
C7 C6 H6 120.2
C6 C7 C2 121.1(5)
C6 C7 H7 119.5
C2 C7 H7 119.5
C9 C8 C1 178.1(4)
C8 C9 C10 179.8(6)
C15 C10 C9 122.3(5)
C15 C10 C11 116.9(4)
C9 C10 C11 120.7(5)
C12 C11 C10 119.3(5)
C12 C11 H11 120.3
C10 C11 H11 120.3
C13 C12 C11 120.8(5)
C13 C12 H12 119.6
C11 C12 H12 119.6
C14 C13 C12 120.1(5)
C14 C13 H13 120.0
C12 C13 H13 120.0
C13 C14 C15 121.8(6)
C13 C14 H14 119.1
C15 C14 H14 119.1
C14 C15 C10 121.1(5)
C14 C15 H15 119.5
C10 C15 H15 119.5
C1 C16 C17 128.5(4)
C1 C16 H16 115.8
C17 C16 H16 115.8
C18 C17 C16 177.5(5)
C17 C18 C19 176.9(5)
C20 C19 C24 117.5(5)
C20 C19 C18 122.0(5)
C24 C19 C18 120.6(5)
C21 C20 C19 121.8(5)
C21 C20 H20 119.1
C19 C20 H20 119.1
C22 C21 C20 121.1(6)
C22 C21 H21 119.4
C20 C21 H21 119.4
C21 C22 C23 118.5(6)
C21 C22 H22 120.8
C23 C22 H22 120.8
C24 C23 C22 120.7(5)
C24 C23 H23 119.7
C22 C23 H23 119.7
C23 C24 C19 120.5(5)
C23 C24 H24 119.8
C19 C24 H24 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C16 1.337(6)
C1 C8 1.470(6)
C1 C2 1.477(6)
C2 C3 1.379(6)
C2 C7 1.408(5)
C3 C4 1.366(6)
C3 H3 0.9300
C4 C5 1.336(6)
C4 H4 0.9300
C5 C6 1.352(7)
C5 H5 0.9300
C6 C7 1.359(6)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.192(5)
C9 C10 1.395(5)
C10 C15 1.362(6)
C10 C11 1.398(7)
C11 C12 1.370(6)
C11 H11 0.9300
C12 C13 1.337(7)
C12 H12 0.9300
C13 C14 1.307(8)
C13 H13 0.9300
C14 C15 1.348(7)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.411(7)
C16 H16 0.9300
C17 C18 1.161(6)
C18 C19 1.431(7)
C19 C20 1.361(6)
C19 C24 1.377(6)
C20 C21 1.352(7)
C20 H20 0.9300
C21 C22 1.344(9)
C21 H21 0.9300
C22 C23 1.374(7)
C22 H22 0.9300
C23 C24 1.365(7)
C23 H23 0.9300
C24 H24 0.9300
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
C16 C1 C2 C3 -170.8(4)
C8 C1 C2 C3 8.7(5)
C16 C1 C2 C7 9.7(6)
C8 C1 C2 C7 -170.8(3)
C7 C2 C3 C4 1.0(6)
C1 C2 C3 C4 -178.5(4)
C2 C3 C4 C5 -1.2(7)
C3 C4 C5 C6 0.6(7)
C4 C5 C6 C7 0.0(7)
C5 C6 C7 C2 -0.1(7)
C3 C2 C7 C6 -0.4(6)
C1 C2 C7 C6 179.1(4)
C16 C1 C8 C9 -143(15)
C2 C1 C8 C9 37(15)
C1 C8 C9 C10 125(100)
C8 C9 C10 C15 3(100)
C8 C9 C10 C11 -173(100)
C15 C10 C11 C12 -2.2(6)
C9 C10 C11 C12 174.1(4)
C10 C11 C12 C13 2.3(8)
C11 C12 C13 C14 -1.1(9)
C12 C13 C14 C15 -0.2(9)
C13 C14 C15 C10 0.2(9)
C9 C10 C15 C14 -175.3(5)
C11 C10 C15 C14 1.0(7)
C8 C1 C16 C17 0.0(6)
C2 C1 C16 C17 179.4(4)
C1 C16 C17 C18 52(11)
C16 C17 C18 C19 -168(9)
C17 C18 C19 C20 107(9)
C17 C18 C19 C24 -74(9)
C24 C19 C20 C21 1.4(7)
C18 C19 C20 C21 -179.9(5)
C19 C20 C21 C22 0.2(9)
C20 C21 C22 C23 -1.3(9)
C21 C22 C23 C24 0.7(8)
C22 C23 C24 C19 0.9(7)
C20 C19 C24 C23 -1.9(6)
C18 C19 C24 C23 179.3(4)
