Synthesis of 2-substituted bicyclo[1.1.0]butanes <i>via</i> zincocyclopropanation using bromoform as the carbenoid precursor.
Thai-Savard, Léa; Charette, André B; Chemical communications (Cambridge, England) 59 (2023) 5273–5276; doi:10.1039/d3cc00335c

data_7131561
_publ_section_title
;
 Synthesis of 2-substituted bicyclo[1.1.0]butanes <i>via</i>
 zincocyclopropanation using bromoform as the carbenoid precursor.
;
_journal_issue                   35
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5273
_journal_page_last               5276
_journal_paper_doi               10.1039/d3cc00335c
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C21 H23 N3 O2'
_chemical_formula_sum            'C21 H23 N3 O2'
_chemical_formula_weight         349.42
_chemical_melting_point          337
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-10
_audit_creation_method
;
FinalCif V104 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2022-05-26 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.548(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3404(6)
_cell_length_b                   5.5177(2)
_cell_length_c                   21.3195(8)
_cell_measurement_reflns_used    7985
_cell_measurement_temperature    150
_cell_measurement_theta_max      55.511
_cell_measurement_theta_min      3.304
_cell_volume                     1788.93(12)
_computing_cell_refinement
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16661
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.915
_diffrn_reflns_theta_min         3.303
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  0.6573
_exptl_absorpt_correction_T_min  0.6005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0831 before and 0.0450 after correction.
The Ratio of minimum to maximum transmission is 0.9136.
The \l/2 correction factor is Not present.
;
_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    1.297
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method 'crystallised from Et2O/Hexanes'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0556P)^2^+0.3054P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2711
_reflns_number_total             3493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00335c2.cif
_cod_data_source_block           cha2562
_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/RSC/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 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7131560--7131561.cif.
;
_cod_database_code               7131561
_shelx_shelxl_version_number     2019/1
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_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.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_olex2_submission_original_sample_id ABC-LTS-1488
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_t_min   0.846
_shelx_estimated_absorpt_t_max   0.991
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 700'
_shelx_res_checksum              34607
_shelx_hkl_checksum              52308