Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and Arylnitroso Compounds.
François, Benjamin; Eberlin, Ludovic; Berrée, Fabienne; Whiting, Andrew; Carboni, Bertrand; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03214

data_4038172
_publ_section_title
;
 Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and
 Arylnitroso Compounds.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03214
_journal_year                    2020
_chemical_formula_moiety         'C20 H26 B N O5'
_chemical_formula_sum            'C20 H26 B N O5'
_chemical_formula_weight         371.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-31
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.573(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8072(10)
_cell_length_b                   10.7432(9)
_cell_length_c                   14.2090(11)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.94
_cell_measurement_theta_min      2.32
_cell_volume                     1933.2(3)
_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 multi-CPU version (Sheldrick, 2008)'
_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 0.999
_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  0.0325
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            44140
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        30.943
_diffrn_reflns_theta_max         30.943
_diffrn_reflns_theta_min         2.320
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0832 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.9678.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.257
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         6129
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0620P)^2^+0.8450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5268
_reflns_number_total             6129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03214_si_001.cif
_cod_data_source_block           15srv085
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4038172
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.972
_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, All C(H,H,H,H) groups
2. Restrained distances
 O3A-C11 \\sim O3B-C11
 with sigma of 0.01
 O3A-N \\sim O3B-N
 with sigma of 0.01
3. Others
 Uiso(H3A)=Uiso(H3B)=Uiso(H3C)=FVAR(1)
 Uiso(H4A)=Uiso(H4B)=Uiso(H4C)=FVAR(2)
 Uiso(H5A)=Uiso(H5B)=Uiso(H5C)=FVAR(3)
 Uiso(H6A)=Uiso(H6B)=Uiso(H6C)=FVAR(4)
 Fixed Sof: H11A(0.875) H11B(0.875) H11C(0.125) H11D(0.125) O3A(0.89) O3B(0.11)
4.a Rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11(H11C,H11D), C12(H12A,H12B), C14(H14A,H14B)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'