Accessing alternative reaction pathways of the intermolecular condensation between homo-propargyl alcohols and terminal alkynes through divergent gold catalysis.
Smith, Courtney A.; Motika, Stephen E.; Wojtas, Lukasz; Shi, Xiaodong; Chemical communications (Cambridge, England) 53 (2017) 2315–2318; doi:10.1039/c6cc09794d

data_7119263
_publ_section_title
;
 Accessing alternative reaction pathways of the intermolecular
 condensation between homo-propargyl alcohols and terminal alkynes through
 divergent gold catalysis.
;
_journal_issue                   15
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2315
_journal_page_last               2318
_journal_paper_doi               10.1039/c6cc09794d
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C24 H16 N4 O'
_chemical_formula_sum            'C24 H16 N4 O'
_chemical_formula_weight         376.41
_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
_audit_creation_date             2016-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.5300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4429(4)
_cell_length_b                   8.4127(2)
_cell_length_c                   15.5871(4)
_cell_measurement_reflns_used    1929
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.978
_cell_measurement_theta_min      27.890
_cell_volume                     1862.00(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.03
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3385
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.231
_diffrn_reflns_theta_min         3.112
_diffrn_source                   'INCOATEC Imus micro-focus source'
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.805781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1408 before and 0.0840 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1449 before and 0.0879 after correction.
 The Ratio of minimum to maximum transmission is 0.81.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 34378 reflections, Rint = 0.0913
 (20167 with I > 3sig(I), Rint = 0.0714)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0649
_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^)+(0.0153P)^2^+2.8489P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1291
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2910
_reflns_number_total             3385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc09794d3.cif
_cod_data_source_block           cas2057a_0m
_cod_depositor_comments
'Adding full bibliography for 7119261--7119263.cif.'
_cod_database_code               7119263
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.835
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7232(18) 0.2768(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C5(H5), C3(H3), C25(H25), C2(H2), C1(H1), C27(H27), C29(H29),
 C28(H28), C26(H26)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'