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_1546290
_publ_section_title
;
 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         'C13 H14 Br2 Si'
_chemical_formula_sum            'C13 H14 Br2 Si'
_chemical_formula_weight         358.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-03-21 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.1754(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1961(4)
_cell_length_b                   7.4763(4)
_cell_length_c                   26.1123(14)
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.149
_cell_measurement_theta_min      3.134
_cell_volume                     1399.12(13)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            48708
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.198
_diffrn_reflns_theta_min         1.566
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    5.852
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0741 before and 0.0426 after correction. The Ratio of minimum to maximum transmission is 0.7723. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         4154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0193
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0189P)^2^+0.6515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0416
_refine_ls_wR_factor_ref         0.0431
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3649
_reflns_number_total             4154
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc01625e2.cif
_cod_data_source_block           cx0925
_cod_database_code               1546290
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.830
_shelx_estimated_absorpt_t_min   0.398
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C8(H8), C10(H10)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              49646
_olex2_date_sample_data_collection 2017-02-07
_olex2_date_sample_submission    2017-02-07
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx0925
_olex2_submission_special_instructions 'No special instructions were received'