Arylation and alkenylation of activated alkyl halides using sulfonamides.
Johnson, Stuart; Kovács, Ervin; Greaney, Michael F.; Chemical communications (Cambridge, England) 56 (2020) 3222–3224; doi:10.1039/d0cc00220h

data_7126013
_publ_section_title
;
 Arylation and alkenylation of activated alkyl halides using sulfonamides.
;
_journal_issue                   21
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3222
_journal_page_last               3224
_journal_paper_doi               10.1039/d0cc00220h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C17 H18 N2 O4'
_chemical_formula_sum            'C17 H18 N2 O4'
_chemical_formula_weight         314.33
_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             2018-08-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2020-01-08 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.389(3)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   18.8960(5)
_cell_length_b                   15.0948(3)
_cell_length_c                   22.5368(7)
_cell_measurement_reflns_used    8714
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.4180
_cell_measurement_theta_min      1.7410
_cell_volume                     6253.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14d (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.775
_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    -20.00  56.00   1.00   20.00    --   -7.80  63.00 102.00   76
  2  \w    -86.00  26.00   1.00   20.00    --   -7.80 -63.00 -33.00  112
  3  \w    -82.00   2.00   1.00   20.00    --    5.00 -57.00 -90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0098926000
_diffrn_orient_matrix_UB_12      -0.0285258000
_diffrn_orient_matrix_UB_13      -0.0255915000
_diffrn_orient_matrix_UB_21      -0.0270777000
_diffrn_orient_matrix_UB_22      -0.0196244000
_diffrn_orient_matrix_UB_23      0.0128993000
_diffrn_orient_matrix_UB_31      -0.0256385000
_diffrn_orient_matrix_UB_32      0.0317684000
_diffrn_orient_matrix_UB_33      -0.0150211000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.775
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25600
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.775
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.640
_diffrn_reflns_theta_min         1.746
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14d (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             2656
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         7484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0587
_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^)+(0.0474P)^2^+9.0095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5860
_reflns_number_total             7484
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc00220h2.cif
_cod_data_source_block           s5292r
_cod_depositor_comments
;
          Adding full bibliography for 7126013.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C17 H18 N2 O4)'
_cod_original_formula_sum        'C34 H36 N4 O8'
_cod_original_formula_units_Z    8
_cod_original_formula_weight     628.67
_cod_database_code               7126013
_shelxl_version_number           2014/6
_chemical_oxdiff_usercomment     grh
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.79
_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, All N(H) groups
2.a Riding coordinates:
 N13(H13), N36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C19(H19), C46(H46), C22(H22), C23(H23), C3(H3), C5(H5), C21(H21),
 C20(H20), C6(H6), C25(H25), C42(H42), C29(H29), C45(H45), C28(H28), C26(H26),
 C44(H44), C43(H43)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C37(H37A,H37B,H37C), C11(H11A,H11B,H11C), C34(H34A,H34B,
 H34C)
;
_shelx_res_checksum              22639
_shelx_hkl_checksum              32458
_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 2.258
_oxdiff_exptl_absorpt_empirical_full_min 0.569