Flow carbonylation of sterically hindered ortho-substituted iodoarenes.
Mallia, Carl J.; Walter, Gary C.; Baxendale, Ian R.; Beilstein journal of organic chemistry 12 (2016) 1503–1511; doi:10.3762/bjoc.12.147

data_4032037
_publ_section_title
;
 Flow carbonylation of sterically hindered ortho-substituted iodoarenes.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1503
_journal_page_last               1511
_journal_paper_doi               10.3762/bjoc.12.147
_journal_volume                  12
_journal_year                    2016
_chemical_formula_moiety         'C24 H33 Br I N O5'
_chemical_formula_sum            'C24 H33 Br I N O5'
_chemical_formula_weight         622.32
_chemical_name_systematic
'4-tert-butyl 2-ethyl 5-(4-bromo-3-iodophenyl)-1-ethyl-4-methylpyrrolidine-2,4-dicarboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                94.4785(19)
_cell_angle_beta                 101.2553(19)
_cell_angle_gamma                116.2515(17)
_cell_formula_units_Z            2
_cell_length_a                   8.8223(5)
_cell_length_b                   9.7894(5)
_cell_length_c                   17.1881(9)
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    120
_cell_measurement_theta_max      34.36
_cell_measurement_theta_min      2.36
_cell_volume                     1282.73(12)
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            34192
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         35.849
_diffrn_reflns_theta_min         2.361
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.839
_exptl_absorpt_correction_T_max  0.8041
_exptl_absorpt_correction_T_min  0.6748
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0739 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.6627.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.112
_refine_diff_density_max         1.893
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         10848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0274
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0240P)^2^+0.5310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0591
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9096
_reflns_number_total             10848
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-12-147-S2.cif
_cod_data_source_block           16srv107
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/Beilstein/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4032037.cif.
;
_cod_database_code               4032037
_shelx_estimated_absorpt_t_max   0.742
_shelx_estimated_absorpt_t_min   0.588
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Uiso(H8A)=Uiso(H8B)=Uiso(H8C)=FVAR(1)
 Uiso(H9A)=Uiso(H9B)=Uiso(H9C)=FVAR(2)
 Uiso(H10A)=Uiso(H10B)=Uiso(H10C)=FVAR(3)
 Uiso(H12A)=Uiso(H12B)=Uiso(H12C)=FVAR(4)
 Uiso(H13A)=Uiso(H13B)=Uiso(H13C)=FVAR(5)
 Uiso(H16A)=Uiso(H16B)=Uiso(H16C)=FVAR(6)
 Uiso(H17A)=Uiso(H17B)=Uiso(H17C)=FVAR(7)
 Uiso(H18A)=Uiso(H18B)=Uiso(H18C)=FVAR(8)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C23(H23), C24(H24)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_shelx_shelxl_version_number     2014/7