Development of a transition metal-free polymerization route to functional conjugated polydiynes from a haloalkyne-based organic reaction
Zhang, Yun; Zhao, Engui; Deng, Haiqin; Lam, Jacky W. Y.; Tang, Ben Zhong; Polym. Chem. 7 (2016) 2492–; doi:10.1039/C6PY00050A

data_1542616
_publ_section_title
;
 Development of a transition metal-free polymerization route to functional
 conjugated polydiynes from a haloalkyne-based organic reaction
;
_journal_issue                   14
_journal_name_full               'Polym. Chem.'
_journal_page_first              2492
_journal_paper_doi               10.1039/C6PY00050A
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'C56 H38, C Cl3'
_chemical_formula_sum            'C57 H38 Cl3'
_chemical_formula_weight         829.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_creation_date             2015-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-09-11 deposited with the CCDC.
2016-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6555(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.65924(8)
_cell_length_b                   9.12014(9)
_cell_length_c                   50.6162(5)
_cell_measurement_reflns_used    9495
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      74.6130
_cell_measurement_theta_min      4.8750
_cell_volume                     4457.10(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega   81.00  178.90   0.5500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7843   45.0000  -30.0000 178

  2 omega  -96.00   45.35   0.5500    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.4812   19.0000   60.0000 257

  3 omega -124.00  -80.00   0.5500    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.4812  -99.0000  -60.0000 80

  4 omega   23.00   94.50   0.5500    8.0000
omega____ theta____ kappa____ phi______ frames
    -       38.4812 -125.0000   90.0000 130

  5 omega   30.00  115.25   0.5500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7843 -111.0000    0.0000 155

  6 omega   30.00  115.25   0.5500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7843 -111.0000  150.0000 155

  7 omega   81.00  178.90   0.5500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7843   45.0000   90.0000 178

  8 omega   25.00  109.70   0.5500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7843  -94.0000 -150.0000 154

  9 omega   34.00  105.50   0.5500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7843  -45.0000 -180.0000 130

 10 omega -116.00   -9.85   0.5500    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.4812  -57.0000    0.0000 193

 11 omega    2.00   31.70   0.5500    8.0000
omega____ theta____ kappa____ phi______ frames
    -       38.4812   77.0000  -90.0000 54
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0065310000
_diffrn_orient_matrix_UB_12      0.1463320000
_diffrn_orient_matrix_UB_13      -0.0151179000
_diffrn_orient_matrix_UB_21      0.0392408000
_diffrn_orient_matrix_UB_22      0.0801334000
_diffrn_orient_matrix_UB_23      0.0259400000
_diffrn_orient_matrix_UB_31      0.1545415000
_diffrn_orient_matrix_UB_32      -0.0263919000
_diffrn_orient_matrix_UB_33      -0.0050507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_limit_l_min       -60
_diffrn_reflns_number            18636
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.996
_diffrn_reflns_theta_min         4.855
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.142
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       plate
_exptl_crystal_F_000             1724
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.472
_refine_diff_density_min         -1.097
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         7798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0895
_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/[\s^2^(Fo^2^)+(0.0980P)^2^+12.9520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2148
_refine_ls_wR_factor_ref         0.2208
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6931
_reflns_number_total             7798
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6py00050a2.cif
_cod_data_source_block           TPEdiyne
_cod_depositor_comments          'Adding full bibliography for 1542616.cif.'
_cod_database_code               1542616
_chemical_oxdiff_formula         'Ph8 C8 Cl2 H2 C2'
_reflns_odcompleteness_completeness 98.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C1S(0.35) C2S(0.4) C3S(0.25) Cl1S(0.45) Cl2S(0.45) Cl3S(0.25)
 Cl4S(0.2) Cl5S(0.3) Cl6S(0.5) Cl7S(0.3) Cl8S(0.25) Cl9S(0.3)
3.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C42(H42),
  C43(H43), C44(H44), C45(H45), C46(H46), C52(H52), C53(H53), C55(H55),
 C56(H56), C62(H62), C63(H63), C64(H64), C65(H65), C66(H66), C72(H72), C73(H73),
  C74(H74), C75(H75), C76(H76), C82(H82), C83(H83), C84(H84), C85(H85), C86(H86)
;
_shelx_res_checksum              40257
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-04-22
_olex2_submission_special_instructions 'No special instructions were received'