An Integrated Console for Capsule-Based, Automated Organic Synthesis
Jiang, Tuo; Bordi, Samuele; McMillan, Angus Erland; Chen, Kuang-Yen; Saito, Fumito; Nichols, Paula L.; Wanner, Benedikt M.; Bode, Jeffrey W.; Chemical Science  (2021) –; doi:10.1039/D1SC01048D

data_1561778
_publ_section_title
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 An Integrated Console for Capsule-Based, Automated Organic Synthesis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01048D
_journal_year                    2021
_chemical_formula_moiety         'C2 F3 O2, C19 H28 N3 O'
_chemical_formula_sum            'C21 H28 F3 N3 O3'
_chemical_formula_weight         427.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-02-20 deposited with the CCDC.	2021-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.443(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   52.9651(13)
_cell_length_b                   8.6539(2)
_cell_length_c                   19.4197(4)
_cell_measurement_reflns_used    8616
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      55.0410
_cell_measurement_theta_min      4.5360
_cell_volume                     8898.3(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
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List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -11.00  35.00   0.50   24.00    --   -1.09  38.00  30.00   92
  2  \w    -13.00  16.00   0.50   24.00    --   -1.09  57.00  90.00   58
  3  \w     -9.00  36.00   0.50   24.00    --   65.61 -38.00 -30.00   90
  4  \w     52.00 141.00   0.50   24.00    --   65.61  19.00 -90.00  178
  5  \w     53.00  91.00   0.50   24.00    --   65.61  19.00-180.00   76
  6  \w     -6.00  42.00   0.50   24.00    --   -1.09  19.00-180.00   96
  7  \w    -22.00   3.00   0.50   24.00    --   -1.09 -19.00-150.00   50
  8  \w     -6.00  68.00   0.50   24.00    --   65.61 -57.00  30.00  148
  9  \w     53.00 115.00   0.50   24.00    --   65.61-130.00 131.00  124
 10  \w    -19.00   7.00   0.50   24.00    --  -67.79  38.00 -60.00   52
 11  \w    -38.00   1.00   0.50   24.00    --  -67.79  38.00-120.00   78
 12  \w    -63.00 -23.00   0.50   24.00    --   -1.09 -19.00-150.00   80
 13  \w    -90.00  -2.00   0.50   24.00    --  -67.79  77.00 -60.00  176
 14  \w    -36.00  -9.00   0.50   24.00    --  -67.79  38.00 120.00   54
 15  \w    -38.00   8.00   0.50   24.00    --  -67.79  38.00 150.00   92
 16  \w     80.00 136.00   0.50   24.00    --   65.61 178.00  90.00  112
 17  \w     83.00 131.00   0.50   24.00    --   65.61 178.00 120.00   96
 18  \w     88.00 136.00   0.50   24.00    --   65.61 178.00 -90.00   96
 19  \w    101.00 126.00   0.50   24.00    --   65.61 178.00-120.00   50
 20  \w    -74.00 -47.00   0.50   24.00    --  -67.79 -77.00-150.00   54
 21  \w   -124.00 -90.00   0.50   24.00    --  -67.79 -77.00-150.00   68
 22  \w   -133.00 -44.00   0.50   24.00    --  -67.79 -77.00-180.00  178
 23  \w    -90.00 -19.00   0.50   24.00    --  -67.79 130.00-156.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0283490000
_diffrn_orient_matrix_UB_12      -0.0400093000
_diffrn_orient_matrix_UB_13      -0.0024450000
_diffrn_orient_matrix_UB_21      0.0064392000
_diffrn_orient_matrix_UB_22      -0.1716457000
_diffrn_orient_matrix_UB_23      0.0120071000
_diffrn_orient_matrix_UB_31      -0.0011359000
_diffrn_orient_matrix_UB_32      0.0250551000
_diffrn_orient_matrix_UB_33      0.0784092000
_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  0.0506
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       55
_diffrn_reflns_limit_h_min       -57
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34793
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        58.459
_diffrn_reflns_theta_max         58.459
_diffrn_reflns_theta_min         1.669
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (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_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       plate
_exptl_crystal_F_000             3616
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     627
_refine_ls_number_reflns         6226
_refine_ls_number_restraints     175
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0618
_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^)+(0.1119P)^2^+5.3235P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1688
_refine_ls_wR_factor_ref         0.1935
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4100
_reflns_number_total             6226
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01048d2.cif
_cod_data_source_block           jb230920_1_1
_cod_database_code               1561778
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C19H27N3O
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     54.18
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2A-H2A = N3A-H3AB = N3A-H3AA = N3B-H3BB = N3B-H3BA = N2B-H2B
 0.93 with sigma of 0.02
 H3BB-H3BA
 1.44 with sigma of 0.02
 H3AB-H3AA
 1.44 with sigma of 0.02
 C2E-C1E \\sim C2D-C1D
 with sigma of 0.02
 F2D-C1D \\sim F3E-C1E \\sim F2E-C1E \\sim F3D-C1D \\sim F1E-C1E \\sim F1D-C1D
 with sigma of 0.02
 O2D-O1D \\sim O2E-O1E
 with sigma of 0.02
 F1D-F2D \\sim F2D-F3D \\sim F3D-F1D \\sim F1E-F2E \\sim F2E-F3E \\sim F3E-F1E
 with sigma of 0.02
 F1C-C2C \\sim F2C-C2C \\sim F3C-C2C \\sim F1D-C2D \\sim F2D-C2D \\sim F3D-C2D
 with sigma of 0.02
 O2D-C2D \\sim O1D-C2D \\sim O1E-C2E \\sim O2E-C2E
 with sigma of 0.02
 O1C-C1C \\sim O2C-C1C \\sim O1D-C1D \\sim O2D-C1D
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C17A, C18A, C19A, N3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1D, F2D, F3D, O1D, O2D, C1D, C2D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1E, F2E, F3E, O1E, O2E, C1E, C2E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F1E)=Sof(F2E)=Sof(F3E)=Sof(O1E)=Sof(O2E)=Sof(C1E)=Sof(C2E)=1-FVAR(1)
 Sof(F1D)=Sof(F2D)=Sof(F3D)=Sof(O1D)=Sof(O2D)=Sof(C1D)=Sof(C2D)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8A(H8A), C14A(H14A), C17A(H17A), C8B(H8B), C14B(H14B), C17B(H17B)
5.b Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C10A(H10A,H10B), C12A(H12A,H12B), C13A(H13A,H13B), C15A(H15A,
 H15B), C16A(H16A,H16B), C9B(H9BA,H9BB), C10B(H10C,H10D), C12B(H12C,H12D),
 C13B(H13C,H13D), C15B(H15C,H15D), C16B(H16C,H16D)
5.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C3B(H3B), C4B(H4B), C6B(H6B), C7B(H7B)
5.d Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C19A(H19A,H19B,H19C), C18B(H18D,H18E,H18F), C19B(H19D,
 H19E,H19F)
;
_shelx_res_checksum              79351
_shelx_hkl_checksum              31881
_olex2_date_sample_data_collection 2020-09-23
_olex2_date_sample_submission    2020-09-23
_olex2_submission_original_sample_id jb230920_1_1
_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 1.495
_oxdiff_exptl_absorpt_empirical_full_min 0.765