#------------------------------------------------------------------------------
#$Date: 2016-08-07 12:40:00 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185642 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/51/7155134.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_7155134
loop_
_publ_author_name
'Chen, Liang'
'Sun, Jing'
'Xie, Ju'
'Yan, Chao-Guo'
_publ_section_title
;
 Molecular diversity of the three-component reaction of α-amino acids,
 dialkyl acetylenedicarboxylates and N-substituted maleimides.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6497
_journal_page_last               6507
_journal_paper_doi               10.1039/c6ob00921b
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C19 H19 Br N2 O6 S'
_chemical_formula_sum            'C19 H19 Br N2 O6 S'
_chemical_formula_weight         483.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc1kk3rz
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-01-11 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                69.617(4)
_cell_angle_beta                 83.083(4)
_cell_angle_gamma                73.659(4)
_cell_formula_units_Z            2
_cell_length_a                   8.8046(14)
_cell_length_b                   10.5597(17)
_cell_length_c                   11.8943(19)
_cell_measurement_reflns_used    9135
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.78
_cell_volume                     994.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14775
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    2.212
_exptl_absorpt_correction_T_max  0.642
_exptl_absorpt_correction_T_min  0.538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0415P)²+0.5572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                3870
_reflns_number_total             4523
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob00921b2.cif
_cod_data_source_block           2f
_cod_depositor_comments
'Adding full bibliography for 7155130--7155143.cif.'
_cod_database_code               7155134
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
Br1 Br 0.35948(4) 0.24141(3) 0.99732(2) 0.05916(12) Uani 1 1 d .
C1 C 0.8509(3) 1.0261(3) 0.8461(2) 0.0442(5) Uani 1 1 d .
H1A H 0.7727 1.0389 0.9087 0.053 Uiso 1 1 calc R
H1B H 0.8742 1.1149 0.8010 0.053 Uiso 1 1 calc R
C2 C 1.0372(3) 0.7966(3) 0.8078(3) 0.0571(7) Uani 1 1 d .
H2A H 1.1443 0.7686 0.7777 0.068 Uiso 1 1 calc R
H2B H 0.9989 0.7139 0.8478 0.068 Uiso 1 1 calc R
C3 C 0.9294(2) 0.8991(2) 0.7071(2) 0.0374(5) Uani 1 1 d .
H3 H 0.9846 0.9678 0.6549 0.045 Uiso 1 1 calc R
C4 C 0.6722(2) 1.0538(2) 0.67972(17) 0.0278(4) Uani 1 1 d .
C5 C 0.7245(2) 1.1786(2) 0.58601(18) 0.0310(4) Uani 1 1 d .
C6 C 0.7321(3) 1.4137(2) 0.5397(2) 0.0497(6) Uani 1 1 d .
H6A H 0.8295 1.3860 0.4981 0.074 Uiso 1 1 calc R
H6B H 0.7459 1.4697 0.5843 0.074 Uiso 1 1 calc R
H6C H 0.6502 1.4670 0.4826 0.074 Uiso 1 1 calc R
C7 C 0.5186(2) 1.1032(2) 0.74454(18) 0.0314(4) Uani 1 1 d .
H7A H 0.4918 1.0224 0.8046 0.038 Uiso 1 1 calc R
H7B H 0.5356 1.1623 0.7860 0.038 Uiso 1 1 calc R
C8 C 0.3813(2) 1.1827(2) 0.6627(2) 0.0335(4) Uani 1 1 d .
C9 C 0.1072(3) 1.2879(3) 0.6617(3) 0.0645(8) Uani 1 1 d .
H9A H 0.1249 1.3688 0.5982 0.097 Uiso 1 1 calc R
H9B H 0.0246 1.3167 0.7150 0.097 Uiso 1 1 calc R
H9C H 0.0764 1.2284 0.6283 0.097 Uiso 1 1 calc R
C10 C 0.5709(2) 0.8488(2) 0.67922(17) 0.0304(4) Uani 1 1 d .
C11 C 0.6749(2) 0.9468(2) 0.61655(17) 0.0291(4) Uani 1 1 d .
H11 H 0.6475 0.9946 0.5320 0.035 Uiso 1 1 calc R
C12 C 0.8448(2) 0.8511(2) 0.62828(19) 0.0342(4) Uani 1 1 d .
H12 H 0.8974 0.8634 0.5492 0.041 Uiso 1 1 calc R
C13 C 0.8252(3) 0.7046(2) 0.6839(2) 0.0374(5) Uani 1 1 d .
C14 C 0.6020(3) 0.5929(2) 0.77459(18) 0.0326(4) Uani 1 1 d .
C15 C 0.6794(3) 0.4843(2) 0.8708(2) 0.0419(5) Uani 1 1 d .
H15 H 0.7773 0.4839 0.8930 0.050 Uiso 1 1 calc R
C16 C 0.6103(3) 0.3766(2) 0.9335(2) 0.0462(5) Uani 1 1 d .
H16 H 0.6620 0.3029 0.9976 0.055 Uiso 1 1 calc R
C17 C 0.4639(3) 0.3788(2) 0.90064(19) 0.0410(5) Uani 1 1 d .
C18 C 0.3884(3) 0.4833(2) 0.8026(2) 0.0415(5) Uani 1 1 d .
H18 H 0.2918 0.4819 0.7795 0.050 Uiso 1 1 calc R
C19 C 0.4582(3) 0.5905(2) 0.73897(19) 0.0373(4) Uani 1 1 d .
H19 H 0.4090 0.6612 0.6721 0.045 Uiso 1 1 calc R
N1 N 0.79551(19) 0.96954(18) 0.76773(15) 0.0320(4) Uani 1 1 d .
N2 N 0.6651(2) 0.71112(17) 0.71480(15) 0.0308(3) Uani 1 1 d .
O1 O 0.7969(2) 1.17322(17) 0.49493(15) 0.0449(4) Uani 1 1 d .
O2 O 0.6882(2) 1.29042(16) 0.62116(15) 0.0442(4) Uani 1 1 d .
O3 O 0.38711(19) 1.21716(18) 0.55567(15) 0.0474(4) Uani 1 1 d .
O4 O 0.25083(18) 1.2126(2) 0.72713(17) 0.0517(4) Uani 1 1 d .
O5 O 0.42931(17) 0.88078(16) 0.69507(16) 0.0427(4) Uani 1 1 d .
O6 O 0.9276(2) 0.59721(18) 0.6988(2) 0.0600(5) Uani 1 1 d .
S1 S 1.02986(10) 0.89365(10) 0.90906(9) 0.0811(3) 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'
S S 0.1246 0.1234 '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
N1 C1 S1 103.68(15)
N1 C1 H1A 111.0
S1 C1 H1A 111.0
N1 C1 H1B 111.0
S1 C1 H1B 111.0
H1A C1 H1B 109.0
C3 C2 S1 104.02(17)
C3 C2 H2A 111.0
S1 C2 H2A 111.0
C3 C2 H2B 111.0
S1 C2 H2B 111.0
H2A C2 H2B 109.0
N1 C3 C2 104.37(19)
N1 C3 C12 101.82(16)
C2 C3 C12 122.5(2)
N1 C3 H3 109.1
C2 C3 H3 109.1
C12 C3 H3 109.1
N1 C4 C7 109.49(15)
N1 C4 C5 111.07(15)
C7 C4 C5 111.23(16)
N1 C4 C11 99.63(14)
C7 C4 C11 117.16(16)
C5 C4 C11 107.71(15)
O1 C5 O2 123.77(19)
O1 C5 C4 123.92(18)
O2 C5 C4 112.21(16)
O2 C6 H6A 109.5
O2 C6 H6B 109.5
H6A C6 H6B 109.5
O2 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C8 C7 C4 113.68(16)
C8 C7 H7A 108.8
C4 C7 H7A 108.8
C8 C7 H7B 108.8
C4 C7 H7B 108.8
H7A C7 H7B 107.7
O3 C8 O4 124.4(2)
O3 C8 C7 125.99(19)
O4 C8 C7 109.61(18)
O4 C9 H9A 109.5
O4 C9 H9B 109.5
H9A C9 H9B 109.5
O4 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O5 C10 N2 124.12(19)
O5 C10 C11 126.83(18)
N2 C10 C11 109.03(16)
C10 C11 C12 104.60(16)
C10 C11 C4 113.37(15)
C12 C11 C4 106.10(15)
C10 C11 H11 110.8
C12 C11 H11 110.8
C4 C11 H11 110.8
C13 C12 C11 105.08(16)
C13 C12 C3 115.07(19)
C11 C12 C3 104.81(15)
C13 C12 H12 110.5
C11 C12 H12 110.5
C3 C12 H12 110.5
O6 C13 N2 124.1(2)
O6 C13 C12 126.9(2)
N2 C13 C12 108.98(17)
C15 C14 C19 120.0(2)
C15 C14 N2 120.49(19)
C19 C14 N2 119.48(18)
C16 C15 C14 119.6(2)
C16 C15 H15 120.2
C14 C15 H15 120.2
C15 C16 C17 119.8(2)
C15 C16 H16 120.1
C17 C16 H16 120.1
C18 C17 C16 121.2(2)
C18 C17 Br1 119.20(19)
C16 C17 Br1 119.51(17)
C17 C18 C19 119.0(2)
C17 C18 H18 120.5
C19 C18 H18 120.5
C18 C19 C14 120.3(2)
C18 C19 H19 119.9
C14 C19 H19 119.9
C1 N1 C3 110.51(17)
C1 N1 C4 122.48(16)
C3 N1 C4 108.23(15)
C10 N2 C13 111.91(17)
C10 N2 C14 122.96(17)
C13 N2 C14 125.13(17)
C5 O2 C6 116.74(18)
C8 O4 C9 116.6(2)
C2 S1 C1 94.32(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C17 1.899(2)
C1 N1 1.457(3)
C1 S1 1.820(2)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.517(3)
C2 S1 1.819(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 N1 1.463(3)
C3 C12 1.550(3)
C3 H3 0.9800
C4 N1 1.465(2)
C4 C7 1.526(3)
C4 C5 1.545(3)
C4 C11 1.554(3)
C5 O1 1.200(3)
C5 O2 1.331(2)
C6 O2 1.448(3)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 C8 1.502(3)
C7 H7A 0.9700
C7 H7B 0.9700
C8 O3 1.195(3)
C8 O4 1.326(3)
C9 O4 1.442(3)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 O5 1.206(2)
C10 N2 1.399(2)
C10 C11 1.515(3)
C11 C12 1.542(3)
C11 H11 0.9800
C12 C13 1.507(3)
C12 H12 0.9800
C13 O6 1.205(3)
C13 N2 1.402(3)
C14 C15 1.387(3)
C14 C19 1.392(3)
C14 N2 1.431(3)
C15 C16 1.382(3)
C15 H15 0.9300
C16 C17 1.383(4)
C16 H16 0.9300
C17 C18 1.378(3)
C18 C19 1.384(3)
C18 H18 0.9300
C19 H19 0.9300
