Ring-expanded N-heterocyclic carbenes as ligands in iron-catalysed cross-coupling reactions of arylmagnesium reagents and aryl chlorides.
Teng, Qiaoqiao; Wu, Wenqin; Duong, Hung A.; Huynh, Han Vinh; Chemical communications (Cambridge, England) 54 (2018) 6044–6047; doi:10.1039/c8cc01808a

data_7121754
_publ_section_title
;
 Ring-expanded N-heterocyclic carbenes as ligands in iron-catalysed
 cross-coupling reactions of arylmagnesium reagents and aryl chlorides.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6044
_journal_page_last               6047
_journal_paper_doi               10.1039/c8cc01808a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C17 H20 I N2 O0.5'
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_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-11-08 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 126.3150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   10.5339(5)
_cell_length_c                   11.1338(6)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.43
_cell_measurement_theta_min      2.27
_cell_volume                     1654.71(14)
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            47242
_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.275
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_diffrn_source                   'Sealed Microfocus Source'
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_exptl_absorpt_correction_T_min  0.6848
_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.192
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
; 
 Flack x determined using 1910 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.010(4)
_refine_ls_extinction_coef       0.0130(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.119
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_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0113
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_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^)+(0.0137P)^2^+0.5366P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0274
_refine_ls_wR_factor_ref         0.0274
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4083
_reflns_number_total             4118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc01808a2.cif
_cod_data_source_block           H264
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7121752--7121754.cif.
;
_cod_original_formula_sum        'C17 H20 I N2 O0.50'
_cod_database_code               7121754
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.568
_shelx_estimated_absorpt_t_max   0.708
_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_shelx_res_checksum              75197