A carbon dioxide-promoted three-component Strecker reaction
Fauziev, Ruslan V.; Ivanov, Roman E.; Kuchurov, Ilya V.; Zlotin, Sergei G.; Green Chemistry 23 (2021) 10137–10144; doi:10.1039/D1GC03161A

data_7243979
_publ_section_title
;
 A carbon dioxide-promoted three-component Strecker reaction
;
_journal_issue                   24
_journal_name_full               'Green Chemistry'
_journal_page_first              10137
_journal_page_last               10144
_journal_paper_doi               10.1039/D1GC03161A
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H19 N2 O, Cl'
_chemical_formula_sum            'C16 H19 Cl N2 O'
_chemical_formula_weight         290.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-07-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-16 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.78804(5)
_cell_length_b                   10.18953(7)
_cell_length_c                   19.93923(14)
_cell_measurement_reflns_used    15410
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.3130
_cell_measurement_theta_min      4.4240
_cell_volume                     1582.307(19)
_computing_cell_refinement       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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     90.00 177.15   0.35    0.50    --  111.50  77.00  90.00  249
  2  \w    101.00 178.00   0.35    0.50    --  111.50  25.00  13.00  220
  3  \w    101.00 178.00   0.35    0.50    --  111.50  15.00 -30.00  220
  4  \w    101.00 178.00   0.35    0.50    --  111.50  30.00-120.00  220
  5  \w    101.00 178.00   0.35    0.50    --  111.50  15.00-180.00  220
  6  \w    -26.00  25.10   0.35    0.50    --  -48.76  19.00-120.00  146
  7  \w   -118.00 -35.75   0.35    0.50    --  -90.00 170.00   0.00  235
  8  \w    -26.00  25.10   0.35    0.50    --  -48.76  19.00 150.00  146
  9  \w    -31.00  25.00   0.35    0.50    --  -48.76  25.00  13.00  160
 10  \w   -121.00 -36.30   0.35    0.50    --  -48.76 -57.00-150.00  242
 11  \w   -121.00 -27.90   0.35    0.50    --  -48.76 -77.00 -60.00  266
 12  \w   -161.00-105.70   0.35    0.50    --  -90.00 -77.00  60.00  158
 13  \w   -121.00 -27.90   0.35    0.50    --  -48.76 -77.00  90.00  266
 14  \w    -25.00  31.00   0.35    0.50    --   48.76 -25.00-150.00  160
 15  \w     95.00 176.90   0.35    0.50    --  111.50 125.00   0.00  234
 16  \w     40.00 103.70   0.35    0.50    --  111.50 -77.00 150.00  182
 17  \w     40.00  69.75   0.35    0.50    --  111.50 -61.00  90.00   85
 18  \w     40.00  69.75   0.35    0.50    --  111.50 -61.00   0.00   85
 19  \w     40.00 103.70   0.35    0.50    --  111.50 -95.00 -60.00  182
 20  \w     57.00 143.10   0.35    0.50    --  111.50-170.00 -15.00  246
 21  \w     40.00 106.85   0.35    0.50    --  111.50-115.00 127.00  191
 22  \w     40.00 106.15   0.35    0.50    --  111.50-103.00  28.00  189
 23  \w     40.00 110.00   0.35    0.50    --  111.50-125.00-180.00  200
;
_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      -0.0341010000
_diffrn_orient_matrix_UB_12      -0.0178685000
_diffrn_orient_matrix_UB_13      -0.0755493000
_diffrn_orient_matrix_UB_21      -0.1867732000
_diffrn_orient_matrix_UB_22      0.0457541000
_diffrn_orient_matrix_UB_23      0.0100187000
_diffrn_orient_matrix_UB_31      0.0554604000
_diffrn_orient_matrix_UB_32      0.1430188000
_diffrn_orient_matrix_UB_33      -0.0126587000
_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  0.0275
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17394
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.647
_diffrn_reflns_theta_min         4.435
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.109
_exptl_absorpt_correction_T_max  0.36450
_exptl_absorpt_correction_T_min  0.28637
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.106a (Rigaku Oxford Diffraction, 2021)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             616
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1,4-dioxane, methanol'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_size_rad          0.104
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1365 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0246
_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^)+(0.0314P)^2^+0.3551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0642
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3329
_reflns_number_total             3379
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc03161a1.cif
_cod_data_source_block           famid
_cod_depositor_comments          'Adding full bibliography for 7243979.cif.'
_cod_original_cell_volume        1582.306(19)
_cod_database_code               7243979
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C64  H76  N8  O4  Cl4'
_chemical_oxdiff_usercomment     FAMID
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.801
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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 Ternary CH refined with riding coordinates:
 C2(H2), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              77134
_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 1.355
_oxdiff_exptl_absorpt_empirical_full_min 0.504