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_1561779
_publ_section_title
;
 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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-28
_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                79.147(4)
_cell_angle_beta                 80.009(3)
_cell_angle_gamma                73.949(4)
_cell_formula_units_Z            2
_cell_length_a                   8.7250(3)
_cell_length_b                   11.2299(6)
_cell_length_c                   12.2001(5)
_cell_measurement_reflns_used    5118
_cell_measurement_temperature    250.0(1)
_cell_measurement_theta_max      74.8440
_cell_measurement_theta_min      3.7240
_cell_volume                     1118.85(9)
_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      250.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_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    -72.00  18.00   0.50    7.00    --  -48.62  77.00 150.00  180
  2  \w    -38.00   6.00   0.50   17.80    --  -70.00  38.00 120.00   88
  3  \w    -38.00   6.00   0.50   17.80    --  -70.00  38.00  60.00   88
  4  \w    -38.00   6.00   0.50   17.80    --  -70.00  38.00 -30.00   88
  5  \w    -38.00   6.00   0.50   17.80    --  -70.00  38.00 -90.00   88
  6  \w    -38.00   6.00   0.50   17.80    --  -70.00  38.00-180.00   88
  7  \w    -68.00   2.00   0.50   17.80    --  -70.00  57.00 -30.00  140
  8  \w   -115.00 -25.00   0.50    7.00    --  -48.62 -77.00  30.00  180
  9  \w   -115.00 -74.00   0.50    7.00    --  -48.62 -77.00 120.00   82
 10  \w   -115.00 -25.00   0.50    7.00    --  -48.62 -77.00 -60.00  180
 11  \w    -27.00   9.00   0.50    7.00    --   48.62 -19.00 -60.00   72
 12  \w     45.00 134.00   0.50   17.80    --  110.00 -77.00  60.00  178
 13  \w     97.00 176.00   0.50   17.80    --  110.00  19.00 120.00  158
 14  \w     94.00 178.00   0.50   17.80    --  110.00  57.00 150.00  168
 15  \w     86.00 176.00   0.50   17.80    --  110.00  77.00  60.00  180
 16  \w     94.00 178.00   0.50   17.80    --  110.00 125.00 120.00  168
 17  \w     98.00 178.00   0.50   17.80    --  110.00  38.00-120.00  160
 18  \w     98.00 178.00   0.50   17.80    --  110.00  38.00-150.00  160
 19  \w     38.00  68.00   0.50   17.80    --  110.00 -57.00   0.00   60
 20  \w     38.00  68.00   0.50   17.80    --  110.00 -57.00 -60.00   60
 21  \w     38.00  68.00   0.50   17.80    --  110.00 -57.00 -90.00   60
 22  \w     38.00  68.00   0.50   17.80    --  110.00 -57.00-150.00   60
 23  \w     38.00  68.00   0.50   17.80    --  110.00 -57.00-120.00   60
 24  \w     40.00 106.00   0.50   17.80    --  110.00 -99.00 -90.00  132
 25  \w     60.00 121.00   0.50    7.00    --   48.62-178.00-150.00  122
 26  \w     39.00 113.00   0.50   17.80    --  110.00-125.00   0.00  148
 27  \w     40.00 106.00   0.50   17.80    --  110.00 -99.00 120.00  132
 28  \w     39.00 113.00   0.50   17.80    --  110.00-125.00  90.00  148
 29  \w     38.00  68.00   0.50   17.80    --  110.00 -57.00  90.00   60
 30  \w     38.00  68.00   0.50   17.80    --  110.00 -57.00 150.00   60
 31  \w     38.00  68.00   0.50   17.80    --  110.00 -57.00  30.00   60
 32  \w     40.00 106.00   0.50   17.80    --  110.00 -99.00 -30.00  132
 33  \w     39.00 113.00   0.50   17.80    --  110.00-125.00 -90.00  148
 34  \w     39.00 113.00   0.50   17.80    --  110.00-125.00-120.00  148
;
_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      -0.1395503000
_diffrn_orient_matrix_UB_12      0.0067125000
_diffrn_orient_matrix_UB_13      -0.0647744000
_diffrn_orient_matrix_UB_21      -0.0587458000
_diffrn_orient_matrix_UB_22      0.1421988000
_diffrn_orient_matrix_UB_23      0.0023938000
_diffrn_orient_matrix_UB_31      0.1067715000
_diffrn_orient_matrix_UB_32      0.0238715000
_diffrn_orient_matrix_UB_33      -0.1122856000
_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  0.0267
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17567
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.627
_diffrn_reflns_theta_min         3.720
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.752
_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    1.269
_exptl_crystal_description       needle
_exptl_crystal_F_000             452
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     688
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0843P)^2^+0.0797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1644
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2915
_reflns_number_total             4740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01048d2.cif
_cod_data_source_block           jb241020_2_1
_cod_database_code               1561779
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H28F3N3O3
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
 N2-H2 = N2A-H2AD
 0.93 with sigma of 0.01
 F1-C21 \\sim F2A-C21A \\sim F1A-C21A \\sim F2-C21 \\sim F3A-C21A \\sim F3-C21
 with sigma of 0.02
 C14-C13 \\sim C15A-C14A \\sim C14A-C13A \\sim C18-C13 \\sim C16A-C15A \\sim
C15-C14 \\sim C18A-C13A ~
 C18-C17 \\sim C18A-C17A \\sim C16-C15 \\sim C17A-C16A \\sim C17-C16
 with sigma of 0.02
 C19-C16 \\sim C19A-C16A
 with sigma of 0.02
 N1-C1 \\sim N1A-C1A
 with sigma of 0.02
 N3-C19 \\sim N3A-C19A
 with sigma of 0.02
 C16-N3 \\sim C16A-N3A
 with sigma of 0.02
 N1-C4 \\sim N1A-C4A
 with sigma of 0.02
 C14-C17 \\sim C15-C18 \\sim C14A-C17A \\sim C15A-C18A
 with sigma of 0.02
 C13-C16 \\sim C13A-C16A
 with sigma of 0.02
 O2-O3 \\sim O2A-O3A
 with sigma of 0.02
 C21A-C20A \\sim C21-C20
 with sigma of 0.02
 F1-F2 \\sim F2-F3 \\sim F3-F1 \\sim F1A-F2A \\sim F2A-F3A \\sim F3A-F1A
 with sigma of 0.02
 C13-C12 \\sim C13A-C12A
 with sigma of 0.02
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C3-C1 \\sim C3A-C1A \\sim C2A-C1A \\sim C2-C1
 with sigma of 0.02
 O2-C20 \\sim O2A-C20A \\sim O3A-C20A \\sim O3-C20
 with sigma of 0.02
 C20-F1 \\sim C20-F2 \\sim C20-F3 \\sim C20A-F1A \\sim C20A-F2A \\sim C20A-F3A
 with sigma of 0.02
 O2-C21 \\sim O2A-C21A \\sim O3-C21 \\sim O3A-C21A
 with sigma of 0.02
 C7-C6 \\sim C5-C4 \\sim C9A-C8A \\sim C8-C7 \\sim C9A-C4A \\sim C8A-C7A \\sim
C6A-C5A \\sim C7A-C6A \\sim C9-
 C4 \\sim C6-C5 \\sim C5A-C4A \\sim C9-C8
 with sigma of 0.02
 C1-C4 \\sim C1A-C4A
 with sigma of 0.02
 O1A-C7A \\sim O1-C7
 with sigma of 0.02
 C12-C11 \\sim C12A-C11A
 with sigma of 0.02
 C7-C10 \\sim C7A-C10A
 with sigma of 0.02
 N2-C10 \\sim N2A-C10A \\sim N2-C12 \\sim N2A-C12A
 with sigma of 0.02
 O1-C11 \\sim O1A-C11A
 with sigma of 0.02
 N2-O1 \\sim N2A-O1A
 with sigma of 0.02
 C10-C11 \\sim C10A-C11A
 with sigma of 0.02
3. Restrained planarity
 C13, C14, C15, C16, C17, C18, C19, C12, N3
 with sigma of 0.1
 C12A, C13A, C14A, C15A, C16A, C17A, C18A, C19A, N3A
 with sigma of 0.1
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C21A)=Sof(C20A)=Sof(O2A)=Sof(O3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(O2)=Sof(O3)=Sof(C20)=Sof(C21)=FVAR(1)
 Sof(C4A)=Sof(H4A)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=
 Sof(C7A)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C3A)=
 Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C1A)=Sof(H1AA)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 Sof(H2AC)=Sof(N1A)=Sof(H1AB)=Sof(H1AC)=Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(N2A)=
 Sof(H2AD)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(O1A)=Sof(C13A)=
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(C17A)=Sof(H17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(N3A)=1-FVAR(2)
 Sof(O1)=Sof(N1)=Sof(H1A)=Sof(H1B)=Sof(N2)=Sof(H2)=Sof(N3)=Sof(C1)=Sof(H1)=
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C4)=
 Sof(H4)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C7)=Sof(C8)=
 Sof(H8A)=Sof(H8B)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C12(H12), C4A(H4A), C1A(H1AA), C12A(H12A)
6.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C9A(H9AA,H9AB), C8A(H8AA,H8AB), C6A(H6AA,H6AB),
 C5A(H5AA,H5AB), N1A(H1AB,H1AC), C10A(H10C,H10D), C11A(H11C,H11D)
6.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18), C14A(H14A), C15A(H15A), C17A(H17A),
 C18A(H18A)
6.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C3A(H3AA,H3AB,H3AC), C2A(H2AA,H2AB,H2AC)
;
_shelx_res_checksum              58338
_shelx_hkl_checksum              81130
_olex2_date_sample_data_collection 2020-10-27
_olex2_date_sample_submission    2020-10-27
_olex2_submission_original_sample_id jb241020_2_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 1.401
_oxdiff_exptl_absorpt_empirical_full_min 0.728