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_4132671
_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         'C20 H23 N'
_chemical_formula_sum            'C20 H23 N'
_chemical_formula_weight         277.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                92.908(3)
_cell_angle_beta                 101.465(4)
_cell_angle_gamma                90.026(3)
_cell_formula_units_Z            4
_cell_length_a                   10.3571(5)
_cell_length_b                   11.0882(4)
_cell_length_c                   14.0186(7)
_cell_measurement_reflns_used    12128
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      29.1670
_cell_measurement_theta_min      2.2510
_cell_volume                     1575.67(13)
_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    -99.00  20.00   1.00   27.50    --   -9.70 -57.00   0.00  119
  2  \w    -99.00  20.00   1.00   27.50    --   -9.70 -57.00 120.00  119
  3  \w    -99.00  23.00   1.00   27.50    --   -9.70 -72.00 -30.00  122
  4  \w    -39.00  80.00   1.00   27.50    --   -9.70  57.00 -60.00  119
  5  \w    -99.00  15.00   1.00   27.50    --   -9.70 -38.00-150.00  114
  6  \w    -42.00  80.00   1.00   27.50    --   -9.70  72.00  30.00  122
  7  \w    -39.00  80.00   1.00   27.50    --   -9.70  57.00-150.00  119
  8  \w    -39.00  80.00   1.00   27.50    --   -9.70  57.00  90.00  119
  9  \w    -42.00  80.00   1.00   27.50    --   -9.70  72.00 -30.00  122
 10  \w    -39.00  80.00   1.00   27.50    --   -9.70  57.00 150.00  119
 11  \w    -42.00 -17.00   1.00   27.50    --   -9.70  72.00-120.00   25
;
_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      0.0514097000
_diffrn_orient_matrix_UB_12      0.0134959000
_diffrn_orient_matrix_UB_13      0.0407906000
_diffrn_orient_matrix_UB_21      -0.0443781000
_diffrn_orient_matrix_UB_22      -0.0084756000
_diffrn_orient_matrix_UB_23      0.0317087000
_diffrn_orient_matrix_UB_31      0.0164689000
_diffrn_orient_matrix_UB_32      -0.0620409000
_diffrn_orient_matrix_UB_33      0.0017736000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            51548
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_min         2.246
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69927
_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    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0842
_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^)+(0.0050P)^2^+4.2000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1519
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5533
_reflns_number_total             5584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05421_si_004.cif
_cod_data_source_block           cd1682
_cod_database_code               4132671
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         N1C20H20
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.978
_reflns_odcompleteness_completeness 99.96
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C39(H39A,H39B), C35(H35A,H35B), C19(H19A,H19B), C36(H36A,
 H36B), C38(H38A,H38B), C18(H18A,H18B), C16(H16A,H16B), C17(H17A,H17B),
 C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C30(H30), C22(H22), C5(H5), C27(H27), C26(H26), C21(H21), C10(H10),
 C32(H32), C8(H8), C13(H13), C1(H1), C6(H6), C2(H2), C28(H28), C33(H33), C7(H7),
  C12(H12)
2.d Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C20(H20A,H20B,H20C)
;
_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 1.420
_oxdiff_exptl_absorpt_empirical_full_min 0.735