#------------------------------------------------------------------------------
#$Date: 2022-11-11 04:19:52 +0200 (Fri, 11 Nov 2022) $
#$Revision: 279224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/57/7245795.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245795
loop_
_publ_author_name
'Weng, Zhibing'
'Zhou, Ying'
'Yue, Xin'
'Jiang, Feng'
'Guo, Wengang'
_publ_section_title
;
 Regioselective α-addition of vinylogous α-ketoester enolate in
 organocatalytic asymmetric Michael reactions: enantioselective synthesis
 of Rauhut--Currier type products
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              32056
_journal_page_last               32060
_journal_paper_doi               10.1039/D2RA06416B
_journal_volume                  12
_journal_year                    2022
_chemical_formula_sum            'C15 H16 Br N O5'
_chemical_formula_weight         370.20
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-03-08 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                96.304(7)
_cell_angle_beta                 112.149(8)
_cell_angle_gamma                105.649(8)
_cell_formula_units_Z            2
_cell_length_a                   8.5887(8)
_cell_length_b                   10.3821(10)
_cell_length_c                   10.6032(8)
_cell_measurement_reflns_used    1680
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.6760
_cell_measurement_theta_min      4.1750
_cell_volume                     819.19(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4070
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6669
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.11
_diffrn_standards_number         6916
_exptl_absorpt_coefficient_mu    2.530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0484P)²+0.3348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1354
_reflns_number_gt                2247
_reflns_number_total             3617
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ra06416b2.cif
_cod_data_source_block           gwg-1
_cod_original_cell_volume        819.19(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7245795
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.12591(7) 0.37743(5) -0.38005(5) 0.0828(2) Uani 1 1 d . . .
C1 C 0.2439(5) 0.5044(4) -0.2032(4) 0.0519(10) Uani 1 1 d . . .
C2 C 0.3748(7) 0.6245(5) -0.1806(5) 0.0727(13) Uani 1 1 d . . .
H2 H 0.4064 0.6450 -0.2528 0.087 Uiso 1 1 calc R . .
C3 C 0.4603(6) 0.7156(5) -0.0518(4) 0.0673(13) Uani 1 1 d . . .
H3 H 0.5500 0.7971 -0.0376 0.081 Uiso 1 1 calc R . .
C4 C 0.4157(4) 0.6886(4) 0.0561(3) 0.0383(8) Uani 1 1 d . . .
C5 C 0.2838(6) 0.5677(4) 0.0306(4) 0.0648(12) Uani 1 1 d . . .
H5 H 0.2508 0.5471 0.1021 0.078 Uiso 1 1 calc R . .
C6 C 0.1974(6) 0.4747(5) -0.0988(5) 0.0724(13) Uani 1 1 d . . .
H6 H 0.1083 0.3926 -0.1135 0.087 Uiso 1 1 calc R . .
C7 C 0.5048(4) 0.7840(4) 0.2025(3) 0.0396(8) Uani 1 1 d . . .
H7 H 0.5468 0.7294 0.2695 0.048 Uiso 1 1 calc R . .
C8 C 0.6682(4) 0.9032(4) 0.2220(4) 0.0464(9) Uani 1 1 d . . .
H8A H 0.7558 0.8673 0.2091 0.056 Uiso 1 1 calc R . .
H8B H 0.6334 0.9555 0.1522 0.056 Uiso 1 1 calc R . .
C9 C 0.3721(4) 0.8352(3) 0.2374(3) 0.0365(8) Uani 1 1 d . . .
C10 C 0.3277(5) 0.8063(4) 0.3416(4) 0.0467(9) Uani 1 1 d . . .
H10 H 0.2453 0.8433 0.3531 0.056 Uiso 1 1 calc R . .
C11 C 0.3932(6) 0.7226(5) 0.4416(4) 0.0691(13) Uani 1 1 d . . .
H11A H 0.4681 0.6820 0.4157 0.104 Uiso 1 1 calc R . .
H11B H 0.2933 0.6512 0.4390 0.104 Uiso 1 1 calc R . .
H11C H 0.4605 0.7805 0.5347 0.104 Uiso 1 1 calc R . .
C12 C 0.2930(4) 0.9213(4) 0.1511(3) 0.0393(8) Uani 1 1 d . . .
C13 C 0.1521(5) 0.9707(4) 0.1744(4) 0.0421(8) Uani 1 1 d . . .
C14 C 0.0863(6) 1.1674(5) 0.2419(5) 0.0616(11) Uani 1 1 d . . .
H14A H -0.0323 1.1200 0.1674 0.074 Uiso 1 1 calc R . .
H14B H 0.0810 1.1607 0.3309 0.074 Uiso 1 1 calc R . .
C15 C 0.1468(9) 1.3111(6) 0.2375(7) 0.106(2) Uani 1 1 d . . .
H15A H 0.2658 1.3564 0.3094 0.159 Uiso 1 1 calc R . .
H15B H 0.0683 1.3552 0.2527 0.159 Uiso 1 1 calc R . .
H15C H 0.1462 1.3167 0.1476 0.159 Uiso 1 1 calc R . .
N1 N 0.7483(4) 0.9948(4) 0.3650(4) 0.0548(9) Uani 1 1 d . . .
O1 O 0.7825(5) 0.9450(4) 0.4654(3) 0.0865(10) Uani 1 1 d . . .
O2 O 0.7724(6) 1.1159(4) 0.3740(4) 0.0964(11) Uani 1 1 d . . .
O3 O 0.3286(3) 0.9538(3) 0.0563(3) 0.0555(7) Uani 1 1 d . . .
O4 O 0.0036(4) 0.8951(3) 0.1422(3) 0.0680(8) Uani 1 1 d . . .
O5 O 0.2124(3) 1.1044(3) 0.2246(3) 0.0530(7) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.0(4) . . ?
C6 C1 Br1 119.4(3) . . ?
C2 C1 Br1 120.6(3) . . ?
C1 C2 C3 120.2(4) . . ?
C4 C3 C2 121.2(4) . . ?
C5 C4 C3 117.4(3) . . ?
C5 C4 C7 118.2(3) . . ?
C3 C4 C7 124.4(3) . . ?
C4 C5 C6 121.9(4) . . ?
C1 C6 C5 119.3(4) . . ?
C9 C7 C8 111.6(3) . . ?
C9 C7 C4 111.5(3) . . ?
C8 C7 C4 112.0(3) . . ?
N1 C8 C7 110.2(3) . . ?
C10 C9 C12 119.7(3) . . ?
C10 C9 C7 123.5(3) . . ?
C12 C9 C7 116.8(3) . . ?
C9 C10 C11 128.3(3) . . ?
O3 C12 C9 123.7(3) . . ?
O3 C12 C13 116.2(3) . . ?
C9 C12 C13 120.1(3) . . ?
O4 C13 O5 126.1(3) . . ?
O4 C13 C12 122.5(3) . . ?
O5 C13 C12 111.3(3) . . ?
C15 C14 O5 108.3(4) . . ?
O2 N1 O1 123.1(4) . . ?
O2 N1 C8 117.7(4) . . ?
O1 N1 C8 119.2(4) . . ?
C13 O5 C14 117.1(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.893(4) . ?
C1 C6 1.350(5) . ?
C1 C2 1.361(6) . ?
C2 C3 1.373(6) . ?
C3 C4 1.371(5) . ?
C4 C5 1.363(5) . ?
C4 C7 1.528(5) . ?
C5 C6 1.386(6) . ?
C7 C9 1.523(4) . ?
C7 C8 1.527(5) . ?
C8 N1 1.490(5) . ?
C9 C10 1.337(4) . ?
C9 C12 1.461(5) . ?
C10 C11 1.488(5) . ?
C12 O3 1.212(4) . ?
C12 C13 1.524(4) . ?
C13 O4 1.196(4) . ?
C13 O5 1.311(4) . ?
C14 C15 1.454(7) . ?
C14 O5 1.463(4) . ?
N1 O2 1.204(5) . ?
N1 O1 1.206(4) . ?
