A predictive model for additions to <i>N</i>-alkyl pyridiniums.
Knight, Brian J.; Tolchin, Zachary A.; Smith, Joel M.; Chemical communications (Cambridge, England) 57 (2021) 2693–2696; doi:10.1039/d1cc00056j

data_7127820
_publ_section_title
;
 A predictive model for additions to <i>N</i>-alkyl pyridiniums.
;
_journal_issue                   21
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2693
_journal_page_last               2696
_journal_paper_doi               10.1039/d1cc00056j
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         '2(C14 H19 Br N O4), Br'
_chemical_formula_sum            'C28 H38 Br3 N2 O8'
_chemical_formula_weight         770.33
_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_block_doi                 10.5517/ccdc.csd.cc269gdd
_audit_creation_date             2019-12-05
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2020-10-01 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                113.1790(10)
_cell_angle_beta                 99.6000(10)
_cell_angle_gamma                103.8560(10)
_cell_formula_units_Z            2
_cell_length_a                   10.89440(10)
_cell_length_b                   13.39160(10)
_cell_length_c                   14.63390(10)
_cell_measurement_reflns_used    30741
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      77.5630
_cell_measurement_theta_min      3.4170
_cell_volume                     1822.23(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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    -54.00  25.00   0.50    0.10    --  -47.12  48.00 128.00  158
  2  \w   -118.00 -33.00   0.50    0.10    --  -47.12 -48.00 -19.00  170
  3  \w    -24.00  54.00   0.50    0.10    --   47.12 -48.00 -19.00  156
  4  \w     34.00 119.00   0.50    0.10    --   47.12  48.00 128.00  170
  5  \w    -54.00 -14.00   0.50    0.50    --  -86.25  48.00 128.00   80
  6  \w   -159.00 -72.00   0.50    0.50    --  -86.25 -48.00 -19.00  174
  7  \w     94.00 178.00   0.50    0.50    --  107.75  48.00 128.00  168
  8  \w   -119.00 -73.00   0.50    0.10    --  -47.12-125.00  90.00   92
  9  \w    -70.00  26.00   0.50    0.10    --  -47.12  77.00-180.00  192
 10  \w   -119.00 -73.00   0.50    0.10    --  -47.12-125.00 -90.00   92
 11  \w     34.00  95.00   0.50    0.10    --   47.12-125.00   0.00  122
 12  \w    -86.00 -13.00   0.50    0.50    --  -86.25 125.00-180.00  146
 13  \w     45.00 126.00   0.50    0.50    --  107.75-145.00-125.59  162
 14  \w     35.00  71.00   0.50    0.50    --  107.75 -61.00   0.00   72
 15  \w     35.00  71.00   0.50    0.50    --  107.75 -61.00-150.00   72
 16  \w     35.00 107.00   0.50    0.50    --  107.75-105.00 -20.45  144
 17  \w     35.00 107.00   0.50    0.50    --  107.75-102.00-130.53  144
 18  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00  90.00  142
 19  \w     85.00 178.00   0.50    0.50    --  107.75  76.00  48.46  186
 20  \w     35.00 112.00   0.50    0.50    --  107.75-125.00  90.00  154
 21  \w     42.00 122.00   0.50    0.50    --  107.75-139.00 124.32  160
 22  \w     35.00 106.00   0.50    0.50    --  107.75 -77.00  90.00  142
 23  \w     95.00 178.00   0.50    0.50    --  107.75  45.00 -30.00  166
 24  \w     35.00  71.00   0.50    0.50    --  107.75 -61.00 150.00   72
 25  \w     95.00 178.00   0.50    0.50    --  107.75 125.00   0.00  166
 26  \w     95.00 178.00   0.50    0.50    --  107.75  30.00 -60.00  166
 27  \w     95.00 178.00   0.50    0.50    --  107.75  45.00   0.00  166
 28  \w     35.00 112.00   0.50    0.50    --  107.75-125.00-120.00  154
 29  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00  60.00  142
 30  \w     35.00 106.00   0.50    0.50    --  107.75 -77.00 150.00  142
 31  \w     94.00 178.00   0.50    0.50    --  107.75  15.00 120.00  168
 32  \w     35.00  71.00   0.50    0.50    --  107.75 -61.00-120.00   72
 33  \w     35.00 108.00   0.50    0.50    --  107.75-111.00 -64.38  146
 34  \w     94.00 178.00   0.50    0.50    --  107.75  15.00  90.00  168
 35  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00 -30.00  142
 36  \w     49.00  82.00   0.50    0.50    --  107.75-125.00 150.00   66
 37  \w     87.00 112.00   0.50    0.50    --  107.75-125.00 150.00   50
 38  \w     49.00 105.00   0.50    0.50    --  107.75 -94.00   0.00  112
 39  \w    104.00 176.00   0.50    0.50    --  107.75  45.00 -60.00  144
 40  \w     88.00 133.00   0.50    0.50    --  107.75  77.00   0.00   90
 41  \w    152.00 178.00   0.50    0.50    --  107.75  77.00   0.00   52
 42  \w     44.00  74.00   0.50    0.50    --  107.75 -77.00-150.00   60
 43  \w     39.00  65.00   0.50    0.50    --  107.75 -97.00 141.93   52
 44  \w     69.00  95.00   0.50    0.50    --  107.75 -97.00 141.93   52
 45  \w     35.00  60.00   0.50    0.50    --  107.75 -61.00 120.00   50
 46  \w     72.00 106.00   0.50    0.50    --  107.75 -94.00-120.00   68
 47  \w     59.00  99.00   0.50    0.50    --  107.75 -94.00 -60.00   80
 48  \w     59.00 102.00   0.50    0.50    --  107.75 -94.00  30.00   86
 49  \w     35.00 112.00   0.50    0.50    --  107.75-125.00 -30.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1209388000
_diffrn_orient_matrix_UB_12      0.0036087000
_diffrn_orient_matrix_UB_13      0.0411578000
_diffrn_orient_matrix_UB_21      0.0582668000
_diffrn_orient_matrix_UB_22      0.1326801000
_diffrn_orient_matrix_UB_23      0.0580523000
_diffrn_orient_matrix_UB_31      -0.0719431000
_diffrn_orient_matrix_UB_32      0.0066800000
_diffrn_orient_matrix_UB_33      -0.0963161000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            39990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.893
_diffrn_reflns_theta_min         3.436
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.469
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.487
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             778
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.166
_refine_diff_density_max         0.844
_refine_diff_density_min         -1.135
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         7684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0693P)^2^+3.0573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7244
_reflns_number_total             7684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00056j2.cif
_cod_data_source_block           bk-2
_cod_depositor_comments          'Adding full bibliography for 7127820.cif.'
_cod_original_cell_volume        1822.22(3)
_cod_database_code               7127820
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H20 Br N O4'
_chemical_oxdiff_usercomment     '0.8, Cu 0.1 and 0.5, 150 K'
_shelx_estimated_absorpt_t_max   0.524
_shelx_estimated_absorpt_t_min   0.344
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C11(H11), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
 C23(H23A,H23B), C24(H24A,H24B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C16(H16), C20(H20)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              15527
_shelx_hkl_checksum              3794
_shelx_fab_checksum              62880
_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 3.031
_oxdiff_exptl_absorpt_empirical_full_min 0.345