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_7131560
_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         'C13 H15 N O5'
_chemical_formula_sum            'C13 H15 N O5'
_chemical_formula_weight         265.26
_chemical_name_systematic
'((1R,2R)-2-Methoxycyclobutyl)methyl 4-nitrobenzoate'
_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             2021-05-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-19 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.284(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2791(1)
_cell_length_b                   26.4160(6)
_cell_length_c                   8.3767(2)
_cell_measurement_reflns_used    6349
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.959
_cell_measurement_theta_min      3.346
_cell_volume                     1311.48(5)
_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      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18080
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.102
_diffrn_reflns_theta_min         3.346
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.02912
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.8
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  0.3857
_exptl_absorpt_correction_T_min  0.2792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1445 before and 0.0485 after correction.
The Ratio of minimum to maximum transmission is 0.7239.
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    1.343
_exptl_crystal_description       Plate
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method 'crystallized from diethylether/Hexanes'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2574
_refine_ls_number_restraints     182
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0509P)^2^+0.7649P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1250
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2408
_reflns_number_total             2574
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00335c2.cif
_cod_data_source_block           cha2402
_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               7131560
_shelx_shelxl_version_number     2018/3
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1A-C2A \\sim C1B-C2B
 with sigma of 0.02
 C2A-C3A \\sim C2B-C3B
 with sigma of 0.02
 C3A-C4A \\sim C3B-C4B
 with sigma of 0.02
 C1A-C4A \\sim C1B-C4B
 with sigma of 0.02
 C1A-C3A \\sim C1A-C3B \\sim C2A-C4A \\sim C2B-C4B
 with sigma of 0.002
 O1A-C5A \\sim O1B-C5B
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
O1A \\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim O1B \\sim C1B \\sim
C2B \\sim C3B \\sim C4B: within 1.7A with sigma of 0.002 and sigma for terminal
atoms of 0.02 within 1.7A
N1 \\sim O4A \\sim O5A \\sim O4B \\sim O5B: within 1.7A with sigma of 0.002 and
sigma for terminal atoms of 0.02 within 1.7A
Uanis(C5A) = Uanis(C5B)
Uanis(O4A) = Uanis(O4B)
Uanis(O5A) = Uanis(O5B)
4. Others
 Sof(H6BC)=Sof(H6BD)=Sof(O1B)=Sof(C1B)=Sof(H1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=
 Sof(H3BA)=Sof(H3BB)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(C5B)=Sof(H5BA)=Sof(H5BB)=
 Sof(H5BC)=1-FVAR(1)
 Sof(H6A)=Sof(H6B)=Sof(O1A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=
 Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=
 Sof(H5AC)=FVAR(1)
 Sof(O4B)=Sof(O5B)=1-FVAR(2)
 Sof(O4A)=Sof(O5A)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C1B(H1B), C2B(H2B)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C6(H6BC,H6BD), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C3B(H3BA,H3BB),
 C4B(H4BA,H4BB)
5.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
5.d Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C5B(H5BA,H5BB,H5BC)
;
_shelx_res_checksum              90949
_shelx_hkl_checksum              88850
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id 'ABC-LTS-1204 '
_olex2_submission_special_instructions 'No special instructions were received'