#------------------------------------------------------------------------------
#$Date: 2021-10-06 18:15:17 +0200 (Wed 06 de Oct de 2021) $
#$Revision: 269778 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/82/7158264.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_7158264
loop_
_publ_author_name
'Chen, Xiao Yun'
'Yuan, Shuxia'
'Chen, Yan'
'Sun, Chenyang'
'Tang, Yaonan'
'Chen, Guang'
'Zhu, Baocheng'
'Chen, Kaiwei'
'Zheng, Shaojun'
'Cheng, Xiaofang'
_publ_section_title
;
 Solvent-controlled two-step one-pot syntheses of α-X (X = Br or Cl)
 enamino ketones/esters and 3-(2,5-dioxopyrrolidin-1-yl)acrylate by using
 terminal carbonyl alkynes.
;
_journal_issue                   36
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7914
_journal_page_last               7919
_journal_paper_doi               10.1039/d1ob01308d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C9 H14 Br N O3'
_chemical_formula_weight         264.12
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc289g68
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-07-04 deposited with the CCDC.	2021-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                109.638(4)
_cell_angle_beta                 92.037(4)
_cell_angle_gamma                101.081(5)
_cell_formula_units_Z            2
_cell_length_a                   4.5418(3)
_cell_length_b                   10.9707(7)
_cell_length_c                   11.8989(6)
_cell_measurement_temperature    296(2)
_cell_volume                     544.76(6)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.974
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5605
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.657
_diffrn_reflns_theta_min         3.163
_exptl_absorpt_coefficient_mu    3.756
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.802
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.070
_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     128
_refine_ls_number_reflns         2473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0355
_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/[σ²(Fo²)+(0.0610P)²+0.0633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2016
_reflns_number_total             2473
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01308d2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7158264.cif.'
_cod_database_code               7158264
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.419
_shelx_estimated_absorpt_t_max   0.520
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.98022(7) 0.14916(3) 0.93394(2) 0.06305(15) Uani 1 1 d . . . . .
C1 C 0.3267(8) -0.3302(3) 0.5712(3) 0.0702(8) Uani 1 1 d . . . . .
H1A H 0.185366 -0.387538 0.502239 0.084 Uiso 1 1 calc R U . . .
H1B H 0.524577 -0.349211 0.556269 0.084 Uiso 1 1 calc R U . . .
C2 C 0.3368(6) -0.1886(3) 0.5856(2) 0.0539(6) Uani 1 1 d . . . . .
H2A H 0.408664 -0.171577 0.515343 0.065 Uiso 1 1 calc R U . . .
H2B H 0.135397 -0.171407 0.592694 0.065 Uiso 1 1 calc R U . . .
C3 C 0.4445(7) -0.2750(3) 0.7762(3) 0.0671(8) Uani 1 1 d . . . . .
H3A H 0.643918 -0.292678 0.762631 0.081 Uiso 1 1 calc R U . . .
H3B H 0.385471 -0.295936 0.846285 0.081 Uiso 1 1 calc R U . . .
C4 C 0.4567(7) -0.1304(3) 0.7999(2) 0.0555(6) Uani 1 1 d . . . . .
H4A H 0.261707 -0.110367 0.819275 0.067 Uiso 1 1 calc R U . . .
H4B H 0.605298 -0.076513 0.867547 0.067 Uiso 1 1 calc R U . . .
C5 C 0.7499(5) -0.0020(2) 0.6850(2) 0.0399(5) Uani 1 1 d . . . . .
H5 H 0.762135 -0.004474 0.606413 0.048 Uiso 1 1 calc R U . . .
C6 C 0.9518(5) 0.1010(2) 0.76498(19) 0.0402(5) Uani 1 1 d . . . . .
C7 C 1.1599(5) 0.1841(2) 0.7162(2) 0.0417(5) Uani 1 1 d . . . . .
C8 C 1.5525(6) 0.3727(3) 0.7541(2) 0.0543(6) Uani 1 1 d . . . . .
H8A H 1.443597 0.416885 0.713824 0.065 Uiso 1 1 calc R U . . .
H8B H 1.668305 0.320788 0.697165 0.065 Uiso 1 1 calc R U . . .
C9 C 1.7572(7) 0.4723(3) 0.8592(3) 0.0697(8) Uani 1 1 d . . . . .
H9A H 1.641160 0.525633 0.913034 0.105 Uiso 1 1 calc R U . . .
H9B H 1.904872 0.528022 0.831767 0.105 Uiso 1 1 calc R U . . .
H9C H 1.857207 0.427271 0.900217 0.105 Uiso 1 1 calc R U . . .
N1 N 0.5379(5) -0.1006(2) 0.69285(18) 0.0461(4) Uani 1 1 d . . . . .
O1 O 0.2377(5) -0.3577(2) 0.6752(2) 0.0731(6) Uani 1 1 d . . . . .
O2 O 1.1692(5) 0.1635(2) 0.60980(16) 0.0650(5) Uani 1 1 d . . . . .
O3 O 1.3430(4) 0.28754(17) 0.79970(16) 0.0504(4) 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'
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'
N N 0.0061 0.0033 '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
O1 C1 C2 111.5(3) . . ?
N1 C2 C1 110.0(2) . . ?
O1 C3 C4 111.9(3) . . ?
N1 C4 C3 108.9(2) . . ?
N1 C5 C6 134.8(2) . . ?
C5 C6 C7 116.90(19) . . ?
C5 C6 Br1 125.91(17) . . ?
C7 C6 Br1 117.17(16) . . ?
O2 C7 O3 122.0(2) . . ?
O2 C7 C6 124.0(2) . . ?
O3 C7 C6 114.03(19) . . ?
O3 C8 C9 107.2(2) . . ?
C5 N1 C4 128.4(2) . . ?
C5 N1 C2 119.5(2) . . ?
C4 N1 C2 112.0(2) . . ?
C3 O1 C1 109.7(2) . . ?
C7 O3 C8 115.42(19) . . ?
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 C6 1.892(2) . ?
C1 O1 1.424(4) . ?
C1 C2 1.495(5) . ?
C2 N1 1.465(3) . ?
C3 O1 1.417(4) . ?
C3 C4 1.505(4) . ?
C4 N1 1.460(3) . ?
C5 N1 1.334(3) . ?
C5 C6 1.357(3) . ?
C6 C7 1.457(3) . ?
C7 O2 1.213(3) . ?
C7 O3 1.337(3) . ?
C8 O3 1.452(3) . ?
C8 C9 1.493(4) . ?
