#------------------------------------------------------------------------------
#$Date: 2016-08-07 12:40:00 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185642 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/51/7155136.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_7155136
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         'C21 H24 N2 O6'
_chemical_formula_sum            'C21 H24 N2 O6'
_chemical_formula_weight         400.42
_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/cc1kk3t1
_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                63.544(5)
_cell_angle_beta                 75.007(5)
_cell_angle_gamma                71.573(5)
_cell_formula_units_Z            2
_cell_length_a                   9.3547(17)
_cell_length_b                   10.5618(19)
_cell_length_c                   11.822(2)
_cell_measurement_reflns_used    4081
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.86
_cell_measurement_theta_min      2.29
_cell_volume                     982.5(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 0.976
_diffrn_measured_fraction_theta_max 0.976
_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  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11140
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0758P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                2259
_reflns_number_total             3371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob00921b2.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 7155130--7155143.cif.'
_cod_database_code               7155136
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
C1 C 0.1098(2) 0.6385(2) 0.29833(19) 0.0330(5) Uani 1 1 d .
H1 H 0.0466 0.5689 0.3530 0.040 Uiso 1 1 calc R
C2 C 0.0137(2) 0.7687(3) 0.2078(2) 0.0493(6) Uani 1 1 d .
H2A H 0.0743 0.8385 0.1513 0.059 Uiso 1 1 calc R
H2B H -0.0698 0.8151 0.2553 0.059 Uiso 1 1 calc R
C3 C -0.0487(3) 0.7207(3) 0.1300(3) 0.0644(8) Uani 1 1 d .
H3A H -0.1183 0.6595 0.1857 0.077 Uiso 1 1 calc R
H3B H -0.1044 0.8053 0.0668 0.077 Uiso 1 1 calc R
C4 C 0.0808(3) 0.6369(3) 0.0637(2) 0.0626(8) Uani 1 1 d .
H4A H 0.1415 0.7026 -0.0011 0.075 Uiso 1 1 calc R
H4B H 0.0389 0.5989 0.0216 0.075 Uiso 1 1 calc R
C5 C 0.1820(3) 0.5120(3) 0.1570(2) 0.0491(6) Uani 1 1 d .
H5A H 0.1249 0.4402 0.2163 0.059 Uiso 1 1 calc R
H5B H 0.2676 0.4656 0.1111 0.059 Uiso 1 1 calc R
C6 C 0.3492(2) 0.4674(2) 0.31433(18) 0.0276(5) Uani 1 1 d .
C7 C 0.2889(2) 0.3346(2) 0.4151(2) 0.0333(5) Uani 1 1 d .
C8 C 0.2675(3) 0.0993(3) 0.4612(3) 0.0641(8) Uani 1 1 d .
H8A H 0.3295 0.0403 0.5282 0.096 Uiso 1 1 calc R
H8B H 0.2697 0.0444 0.4141 0.096 Uiso 1 1 calc R
H8C H 0.1647 0.1287 0.4975 0.096 Uiso 1 1 calc R
C9 C 0.5004(2) 0.4208(2) 0.23932(19) 0.0331(5) Uani 1 1 d .
H9A H 0.4861 0.3636 0.1996 0.040 Uiso 1 1 calc R
H9B H 0.5300 0.5071 0.1717 0.040 Uiso 1 1 calc R
C10 C 0.6269(2) 0.3341(2) 0.3181(2) 0.0336(5) Uani 1 1 d .
C11 C 0.8921(3) 0.2300(3) 0.3061(3) 0.0656(8) Uani 1 1 d .
H11A H 0.9099 0.2786 0.3514 0.098 Uiso 1 1 calc R
H11B H 0.9786 0.2197 0.2434 0.098 Uiso 1 1 calc R
H11C H 0.8764 0.1356 0.3651 0.098 Uiso 1 1 calc R
C12 C 0.2148(2) 0.8120(2) 0.33209(19) 0.0343(5) Uani 1 1 d .
C13 C 0.1896(2) 0.6613(2) 0.38457(19) 0.0309(5) Uani 1 1 d .
H13 H 0.1348 0.6349 0.4716 0.037 Uiso 1 1 calc R
C14 C 0.3498(2) 0.5624(2) 0.38239(18) 0.0256(5) Uani 1 1 d .
H14 H 0.3744 0.5019 0.4692 0.031 Uiso 1 1 calc R
C15 C 0.4540(2) 0.6659(2) 0.30923(18) 0.0284(5) Uani 1 1 d .
C16 C 0.4281(2) 0.9352(2) 0.21150(18) 0.0298(5) Uani 1 1 d .
C17 C 0.5632(2) 0.9379(2) 0.2365(2) 0.0406(6) Uani 1 1 d .
H17 H 0.6136 0.8594 0.3008 0.049 Uiso 1 1 calc R
C18 C 0.6221(3) 1.0595(3) 0.1641(2) 0.0505(6) Uani 1 1 d .
H18 H 0.7129 1.0626 0.1800 0.061 Uiso 1 1 calc R
C19 C 0.5484(3) 1.1759(2) 0.0690(2) 0.0487(6) Uani 1 1 d .
H19 H 0.5903 1.2563 0.0199 0.058 Uiso 1 1 calc R
C20 C 0.4125(3) 1.1733(2) 0.0465(2) 0.0465(6) Uani 1 1 d .
H20 H 0.3610 1.2531 -0.0163 0.056 Uiso 1 1 calc R
C21 C 0.3524(2) 1.0525(2) 0.1172(2) 0.0398(6) Uani 1 1 d .
H21 H 0.2612 1.0501 0.1013 0.048 Uiso 1 1 calc R
N1 N 0.23711(17) 0.56791(18) 0.22709(15) 0.0318(4) Uani 1 1 d .
N2 N 0.36709(17) 0.80847(17) 0.28005(15) 0.0290(4) Uani 1 1 d .
O1 O 0.21065(17) 0.33103(16) 0.51392(14) 0.0489(4) Uani 1 1 d .
O2 O 0.32531(18) 0.22598(16) 0.37697(15) 0.0518(5) Uani 1 1 d .
O3 O 0.61409(17) 0.28520(16) 0.43239(15) 0.0487(4) Uani 1 1 d .
O4 O 0.75894(15) 0.31435(17) 0.24369(14) 0.0494(4) Uani 1 1 d .
O5 O 0.12042(17) 0.92043(16) 0.33380(17) 0.0552(5) Uani 1 1 d .
O6 O 0.59006(15) 0.63385(14) 0.28112(14) 0.0414(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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 110.15(17)
N1 C1 C13 103.05(15)
C2 C1 C13 118.63(18)
N1 C1 H1 108.2
C2 C1 H1 108.2
C13 C1 H1 108.2
C1 C2 C3 109.3(2)
C1 C2 H2A 109.8
C3 C2 H2A 109.8
C1 C2 H2B 109.8
C3 C2 H2B 109.8
H2A C2 H2B 108.3
C4 C3 C2 110.24(19)
C4 C3 H3A 109.6
C2 C3 H3A 109.6
C4 C3 H3B 109.6
C2 C3 H3B 109.6
H3A C3 H3B 108.1
C3 C4 C5 111.8(2)
C3 C4 H4A 109.2
C5 C4 H4A 109.2
C3 C4 H4B 109.2
C5 C4 H4B 109.2
H4A C4 H4B 107.9
N1 C5 C4 109.36(19)
N1 C5 H5A 109.8
C4 C5 H5A 109.8
N1 C5 H5B 109.8
C4 C5 H5B 109.8
H5A C5 H5B 108.3
N1 C6 C9 110.40(15)
N1 C6 C7 111.09(15)
C9 C6 C7 111.09(16)
N1 C6 C14 100.18(14)
C9 C6 C14 115.95(16)
C7 C6 C14 107.65(15)
O1 C7 O2 123.15(19)
O1 C7 C6 124.41(19)
O2 C7 C6 112.31(17)
O2 C8 H8A 109.5
O2 C8 H8B 109.5
H8A C8 H8B 109.5
O2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C6 114.14(16)
C10 C9 H9A 108.7
C6 C9 H9A 108.7
C10 C9 H9B 108.7
C6 C9 H9B 108.7
H9A C9 H9B 107.6
O3 C10 O4 123.6(2)
O3 C10 C9 125.86(19)
O4 C10 C9 110.49(17)
O4 C11 H11A 109.5
O4 C11 H11B 109.5
H11A C11 H11B 109.5
O4 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O5 C12 N2 124.41(19)
O5 C12 C13 126.64(18)
N2 C12 C13 108.94(16)
C12 C13 C14 104.79(15)
C12 C13 C1 113.36(16)
C14 C13 C1 105.24(15)
C12 C13 H13 111.0
C14 C13 H13 111.0
C1 C13 H13 111.0
C15 C14 C13 104.65(15)
C15 C14 C6 113.33(15)
C13 C14 C6 106.19(15)
C15 C14 H14 110.8
C13 C14 H14 110.8
C6 C14 H14 110.8
O6 C15 N2 124.33(17)
O6 C15 C14 126.86(18)
N2 C15 C14 108.80(16)
C21 C16 C17 120.59(19)
C21 C16 N2 118.85(18)
C17 C16 N2 120.53(18)
C16 C17 C18 118.7(2)
C16 C17 H17 120.6
C18 C17 H17 120.6
C19 C18 C17 121.0(2)
C19 C18 H18 119.5
C17 C18 H18 119.5
C18 C19 C20 119.8(2)
C18 C19 H19 120.1
C20 C19 H19 120.1
C19 C20 C21 120.0(2)
C19 C20 H20 120.0
C21 C20 H20 120.0
C16 C21 C20 119.8(2)
C16 C21 H21 120.1
C20 C21 H21 120.1
C5 N1 C1 111.11(16)
C5 N1 C6 118.56(17)
C1 N1 C6 108.00(14)
C12 N2 C15 111.65(16)
C12 N2 C16 123.95(16)
C15 N2 C16 124.31(16)
C7 O2 C8 116.88(17)
C10 O4 C11 117.14(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.470(2)
C1 C2 1.500(3)
C1 C13 1.543(3)
C1 H1 0.9800
C2 C3 1.524(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.521(4)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.519(3)
C4 H4A 0.9700
C4 H4B 0.9700
C5 N1 1.466(3)
C5 H5A 0.9700
C5 H5B 0.9700
C6 N1 1.473(3)
C6 C9 1.526(3)
C6 C7 1.539(3)
C6 C14 1.543(3)
C7 O1 1.199(2)
C7 O2 1.330(3)
C8 O2 1.437(3)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C10 1.494(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 O3 1.200(2)
C10 O4 1.335(2)
C11 O4 1.442(3)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 O5 1.210(2)
C12 N2 1.394(2)
C12 C13 1.502(3)
C13 C14 1.533(3)
C13 H13 0.9800
C14 C15 1.512(3)
C14 H14 0.9800
C15 O6 1.206(2)
C15 N2 1.399(2)
C16 C21 1.379(3)
C16 C17 1.382(3)
C16 N2 1.432(2)
C17 C18 1.381(3)
C17 H17 0.9300
C18 C19 1.372(3)
C18 H18 0.9300
C19 C20 1.375(3)
C19 H19 0.9300
C20 C21 1.380(3)
C20 H20 0.9300
C21 H21 0.9300
