Rapid Access to Substituted 2-Naphthyne Intermediates via the Benzannulation of Halogenated Silylacetylenes
Hein, Samuel J.; Lehnherr, Dan; Dichtel, William; Chem. Sci.  (2017) –; doi:10.1039/C7SC01625E

data_1546289
_publ_section_title
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 Rapid Access to Substituted 2-Naphthyne Intermediates via the
 Benzannulation of Halogenated Silylacetylenes
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC01625E
_journal_year                    2017
_chemical_formula_moiety         'C36 H44'
_chemical_formula_sum            'C36 H44'
_chemical_formula_weight         476.71
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-10-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-03-21 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                88.129(2)
_cell_angle_beta                 79.474(2)
_cell_angle_gamma                86.662(2)
_cell_formula_units_Z            1
_cell_length_a                   8.2828(4)
_cell_length_b                   8.9132(4)
_cell_length_c                   9.1524(4)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.775
_cell_measurement_theta_min      2.264
_cell_volume                     663.02(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'QuazarTM optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14580
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.775
_diffrn_reflns_theta_max         25.775
_diffrn_reflns_theta_min         2.289
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1614 before and 0.0736 after correction.
The Ratio of minimum to maximum transmission is 0.8221.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.686
_exptl_crystal_size_mid          0.481
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0677P)^2^+0.3516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2419
_reflns_number_total             2529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc01625e2.cif
_cod_data_source_block           cx0864_0m
_cod_database_code               1546289
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C11(H11), C13(H13)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C)
;