Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated Dienes and Polyenes.
Nguyen, Vu T.; Dang, Hang T.; Pham, Hoang H.; Nguyen, Viet D.; Flores-Hansen, Carsten; Arman, Hadi D.; Larionov, Oleg V.; Journal of the American Chemical Society 140 (2018) 8434–8438; doi:10.1021/jacs.8b05421

data_4132673
_publ_section_title
;
 Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated
 Dienes and Polyenes.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8434
_journal_page_last               8438
_journal_paper_doi               10.1021/jacs.8b05421
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C13 H10 Cl N'
_chemical_formula_sum            'C13 H10 Cl N'
_chemical_formula_weight         215.67
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.764(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9327(2)
_cell_length_b                   20.3504(8)
_cell_length_c                   12.8881(5)
_cell_measurement_reflns_used    5046
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      26.9640
_cell_measurement_theta_min      2.5400
_cell_volume                     1026.25(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_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      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -25.00  94.00   1.00   57.00    --    4.20  57.00-150.00  119
  2  \w    -99.00  20.00   1.00   57.00    --   -9.60 -57.00 150.00  119
  3  \w    -47.00  80.00   1.00   57.00    --   -9.60  19.00 -30.00  127
  4  \w    -34.00  80.00   1.00   57.00    --   -9.60  38.00-150.00  114
  5  \w    -42.00  80.00   1.00   57.00    --   -9.60  72.00   0.00  122
  6  \w    -99.00  20.00   1.00   57.00    --   -9.60 -57.00 -90.00  119
  7  \w    -42.00  80.00   1.00   57.00    --   -9.60  72.00-120.00  122
  8  \w    -39.00  80.00   1.00   57.00    --   -9.60  57.00  60.00  119
  9  \w    -39.00  80.00   1.00   57.00    --   -9.60  57.00 120.00  119
 10  \w    -42.00  28.00   1.00   57.00    --   -9.60  72.00 -90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0514215000
_diffrn_orient_matrix_UB_12      0.0332075000
_diffrn_orient_matrix_UB_13      0.0076724000
_diffrn_orient_matrix_UB_21      -0.1555134000
_diffrn_orient_matrix_UB_22      0.0105702000
_diffrn_orient_matrix_UB_23      -0.0275619000
_diffrn_orient_matrix_UB_31      -0.0776625000
_diffrn_orient_matrix_UB_32      0.0007506000
_diffrn_orient_matrix_UB_33      0.0473356000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1065
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            30425
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.546
_diffrn_reflns_theta_max         24.546
_diffrn_reflns_theta_min         2.555
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       plank
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0854
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0010P)^2^+5.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1486
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1693
_reflns_number_total             1725
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05421_si_002.cif
_cod_data_source_block           cd1685d
_cod_database_code               4132673
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         N1Cl1C13H12
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.907
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4), C9(H9), C10(H10), C8(H8), C11(H11), C12(H12)
2.b X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.685
_oxdiff_exptl_absorpt_empirical_full_min 0.808