Chemo- and regioselective ring-opening of donor-acceptor oxiranes with <i>N</i>-heteroaromatics.
Sang, Ji-Wei; Xie, Ming-Sheng; Wang, Man-Man; Qu, Gui-Rong; Guo, Hai-Ming; Chemical communications (Cambridge, England) 57 (2021) 4552–4555; doi:10.1039/d1cc00600b

data_7128135
_publ_section_title
;
 Chemo- and regioselective ring-opening of donor-acceptor oxiranes with
 <i>N</i>-heteroaromatics.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4552
_journal_page_last               4555
_journal_paper_doi               10.1039/d1cc00600b
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C19 H19 Cl N4 O5'
_chemical_formula_sum            'C19 H19 Cl N4 O5'
_chemical_formula_weight         418.83
_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             2020-10-23
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2020-10-23 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                89.985(6)
_cell_angle_beta                 87.821(6)
_cell_angle_gamma                80.497(6)
_cell_formula_units_Z            6
_cell_length_a                   11.8048(9)
_cell_length_b                   15.1785(10)
_cell_length_c                   16.7524(12)
_cell_measurement_reflns_used    7241
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.8820
_cell_measurement_theta_min      2.3220
_cell_volume                     2958.3(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -52.00  63.00   1.00    4.00    --  -11.27   0.00 -90.00  115
  2  \w     -9.00  23.00   1.00    4.00    --  -11.27 -99.00 -60.00   32
  3  \w     -2.00  27.00   1.00    4.00    --  -11.27 -99.00-107.00   29
  4  \w     11.00  50.00   1.00    4.00    --   11.90 -99.00 -90.00   39
  5  \w     67.00  94.00   1.00    4.00    --   11.90-178.00-120.00   27
  6  \w    -35.00  54.00   1.00    4.00    --  -11.27  37.00 150.00   89
  7  \w    -51.00 -24.00   1.00    4.00    --  -11.27  99.00  -1.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0400948000
_diffrn_orient_matrix_UB_12      -0.0173712000
_diffrn_orient_matrix_UB_13      -0.0234391000
_diffrn_orient_matrix_UB_21      -0.0138974000
_diffrn_orient_matrix_UB_22      -0.0265058000
_diffrn_orient_matrix_UB_23      0.0326711000
_diffrn_orient_matrix_UB_31      -0.0437803000
_diffrn_orient_matrix_UB_32      0.0352252000
_diffrn_orient_matrix_UB_33      0.0133734000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0762
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23126
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.032
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     821
_refine_ls_number_reflns         10386
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0752
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0951P)^2^+2.9486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.2015
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7712
_reflns_number_total             10386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00600b2.cif
_cod_data_source_block           7828
_cod_depositor_comments
'Adding full bibliography for 7128134--7128140.cif.'
_cod_database_code               7128135
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Restrained distances
 C58-C37 = C2A-C38
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C58) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C37) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C2A) \\sim Ueq, Uanis(C38) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(C38) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
4. Others
 Sof(O0)=1-FVAR(1)
 Sof(O15)=FVAR(1)
 Sof(C38)=Sof(H38A)=Sof(H38B)=1-FVAR(2)
 Sof(C37)=Sof(H37A)=Sof(H37B)=FVAR(2)
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=1-FVAR(3)
 Sof(C58)=Sof(H58A)=Sof(H58B)=Sof(H58C)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C6(H6), C13(H13), C25(H25), C32(H32), C45(H45), C51(H51)
5.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C18(H18A,H18B), C34(H34A,H34B), C37(H37A,H37B), C38(H38A,
 H38B), C53(H53A,H53B), C56(H56A,H56B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C21(H21),
 C24(H24), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C40(H40), C41(H41),
  C42(H42), C43(H43), C44(H44), C46(H46), C49(H49)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C35(H35A,H35B,H35C), C58(H58A,H58B,
 H58C), C2A(H2AA,H2AB,H2AC), C54(H54A,H54B,H54C), C57(H57A,H57B,H57C)
;
_shelx_res_checksum              28777
_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 1.630
_oxdiff_exptl_absorpt_empirical_full_min 0.591