Consecutive photochemical reactions enabled by a dual flow reactor coil strategy
Crawford, Ruairi; Di Filippo, Mara; Guthrie, Duncan; Baumann, Marcus; Chemical Communications  (2022) –; doi:10.1039/D2CC05601A

data_7130986
_publ_section_title
;
 Consecutive photochemical reactions enabled by a dual flow reactor coil
 strategy
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC05601A
_journal_year                    2022
_chemical_formula_moiety         'C19 H17 N O2'
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.33
_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_creation_date             2022-03-22
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-10-11 deposited with the CCDC.	2022-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                102.5580(10)
_cell_angle_beta                 101.4380(10)
_cell_angle_gamma                104.3690(10)
_cell_formula_units_Z            4
_cell_length_a                   10.26560(10)
_cell_length_b                   10.37350(10)
_cell_length_c                   15.2757(2)
_cell_measurement_reflns_used    23002
_cell_measurement_temperature    104(1)
_cell_measurement_theta_max      76.6280
_cell_measurement_theta_min      3.0460
_cell_volume                     1482.37(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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      104(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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    -69.00  30.00   0.50    1.00    --  -40.50  66.00 -21.00  198
  2  \w    -28.00  72.00   0.50    1.00    --   43.21 -66.00-156.00  200
  3  \w     15.00 114.00   0.50    1.00    --   43.21  66.00 -21.00  198
  4  \w     40.00 140.00   0.50    4.00    --  111.00 -66.00-156.00  200
  5  \w     82.00 178.00   0.50    4.00    --  111.00  66.00 -21.00  192
  6  \w    -63.00  32.00   0.50    1.00    --  -40.50  37.00 -30.00  190
  7  \w   -111.00 -12.00   0.50    1.00    --  -40.50 -66.00-156.00  198
  8  \w    -67.00  30.00   0.50    1.00    --  -40.50  57.00 120.00  194
  9  \w     11.00  42.00   0.50    1.00    --   43.21  79.00-160.81   62
 10  \w     11.00  42.00   0.50    1.00    --   43.21  81.00  42.87   62
 11  \w     12.00  42.00   0.50    1.00    --   43.21  77.00 137.57   60
 12  \w     30.00 107.00   0.50    4.00    --  111.00 -94.00   0.00  154
 13  \w     36.00 109.00   0.50    4.00    --  111.00-111.00-150.00  146
 14  \w    103.00 178.00   0.50    4.00    --  111.00  77.00-120.00  150
 15  \w     36.00 109.00   0.50    4.00    --  111.00-111.00-120.00  146
 16  \w     87.00 178.00   0.50    4.00    --  111.00  45.00 150.00  182
 17  \w     36.00 109.00   0.50    4.00    --  111.00-111.00-180.00  146
 18  \w     36.00 135.00   0.50    4.00    --  111.00 -30.00-150.00  198
 19  \w     36.00 109.00   0.50    4.00    --  111.00-111.00 120.00  146
 20  \w    103.00 178.00   0.50    4.00    --  111.00  77.00-150.00  150
 21  \w     61.00 146.00   0.50    4.00    --  111.00 178.00-150.00  170
 22  \w     37.00 142.00   0.50    4.00    --  111.00 -77.00  60.00  210
 23  \w    103.00 178.00   0.50    4.00    --  111.00  77.00 -60.00  150
 24  \w     36.00 109.00   0.50    4.00    --  111.00-111.00 -30.00  146
 25  \w     36.00 109.00   0.50    4.00    --  111.00-111.00 -90.00  146
 26  \w     36.00 109.00   0.50    4.00    --  111.00-111.00  30.00  146
 27  \w     30.00 107.00   0.50    4.00    --  111.00 -94.00 -60.00  154
 28  \w     66.00 178.00   0.50    4.00    --  111.00  15.00  90.00  224
 29  \w     36.00 109.00   0.50    4.00    --  111.00-111.00  90.00  146
 30  \w     36.00 109.00   0.50    4.00    --  111.00-111.00  60.00  146
 31  \w    104.00 178.00   0.50    4.00    --  111.00 111.00 150.00  148
 32  \w     12.00  42.00   0.50    1.00    --   43.21  78.00 -70.44   60
 33  \w     17.00 113.00   0.50    1.00    --   43.21  57.00 120.00  192
 34  \w     12.00  42.00   0.50    1.00    --   43.21  78.00  87.74   60
 35  \w     21.00 116.00   0.50    1.00    --   43.21  37.00  30.00  190
 36  \w     27.00  98.00   0.50    1.00    --   43.21-125.00 120.00  142
 37  \w     11.00  42.00   0.50    1.00    --   43.21  81.00-124.46   62
 38  \w     21.00 116.00   0.50    1.00    --   43.21  37.00 -60.00  190
 39  \w     83.00 178.00   0.50    4.00    --  111.00  61.00  90.00  190
 40  \w     83.00 178.00   0.50    4.00    --  111.00  61.00 -60.00  190
 41  \w     87.00 178.00   0.50    4.00    --  111.00  30.00-150.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1234955000
_diffrn_orient_matrix_UB_12      -0.1206843000
_diffrn_orient_matrix_UB_13      -0.0008502000
_diffrn_orient_matrix_UB_21      0.0426785000
_diffrn_orient_matrix_UB_22      -0.1002529000
_diffrn_orient_matrix_UB_23      -0.0709800000
_diffrn_orient_matrix_UB_31      0.0936233000
_diffrn_orient_matrix_UB_32      -0.0299909000
_diffrn_orient_matrix_UB_33      0.0803411000
_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  0.0141
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30670
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.891
_diffrn_reflns_theta_min         3.075
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.660
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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 intense colourless'
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         6172
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0500P)^2^+0.6852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5985
_reflns_number_total             6172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05601a2.cif
_cod_data_source_block           bau48
_cod_database_code               7130986
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C19H17NO2
_chemical_oxdiff_usercomment     RC-1-6
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.885
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O22B-C18A
 1.44 with sigma of 0.02
 O22B-C21B
 1.42 with sigma of 0.02
 O19B-C18B
 1.44 with sigma of 0.02
 C17-O22B
 1.42 with sigma of 0.02
 C18B-C17
 1.5 with sigma of 0.01
 C21B-C20
 1.5 with sigma of 0.01
 C20-O19B
 1.44 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C18B) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O19B) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O22B) \\sim Ueq, Uanis(C21B) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(O22B) \\sim Ueq, Uanis(O19B) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 C20, O19B, C18B, C17
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C20, C21B, O22B, C17
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(H17)=Sof(C18B)=Sof(H18C)=Sof(H18D)=Sof(H20A)=Sof(H20B)=Sof(C21B)=
 Sof(H21C)=Sof(H21D)=Sof(O19B)=Sof(O22B)=1-FVAR(1)
 Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(H20C)=Sof(H20D)=Sof(C21A)=
 Sof(H21A)=Sof(H21B)=Sof(O19A)=Sof(O22A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C17(H17A), C17(H17), C39(H39)
6.b Secondary CH2 refined with riding coordinates:
 C18A(H18A,H18B), C18B(H18C,H18D), C20(H20C,H20D), C20(H20A,H20B), C21A(H21A,
 H21B), C21B(H21C,H21D), C41(H41A,H41B), C42(H42A,H42B), C44(H44A,H44B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C6(H6), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C25(H25), C26(H26), C27(H27), C28(H28), C31(H31), C34(H34),
  C35(H35), C36(H36), C37(H37), C38(H38)
;
_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 1.216
_oxdiff_exptl_absorpt_empirical_full_min 0.891