#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:44:55 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180194 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/90/7109036.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_7109036
loop_
_publ_author_name
'Lei Zhang'
'Mingyue Zheng'
'Yun Zhai'
'Hong Liu'
_publ_section_title
;
 Rapid and selective access to three distinct sets of indole-based
 heterocycles from a single set of Ugi-adducts under microwave heating
;
_journal_name_full               Chem.Commun.
_journal_page_first              2894
_journal_paper_doi               10.1039/c3cc00111c
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H32 N3 O3'
_chemical_formula_weight         446.56
_chemical_name_systematic
;
?
;
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.19560(10)
_cell_length_b                   17.75810(10)
_cell_length_c                   18.1464(2)
_cell_measurement_reflns_used    7976
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.30
_cell_measurement_theta_min      3.69
_cell_volume                     5218.96(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17440
_diffrn_reflns_theta_full        67.49
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         3.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  0.9709
_exptl_absorpt_correction_T_min  0.8418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4631
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1348P)²+1.0852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1820
_refine_ls_wR_factor_ref         0.1869
_reflns_number_gt                4364
_reflns_number_total             4631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc00111c.txt
_cod_data_source_block           dm11107
_cod_original_sg_symbol_H-M      C222(1)
_cod_database_code               7109036
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, -z'
'-x, y, -z+1/2'
'-x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
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
N1 N 0.04277(13) 0.11433(11) 0.94281(11) 0.0398(4) Uani 1 1 d .
N2 N -0.00642(14) 0.25384(11) 0.83760(11) 0.0420(4) Uani 1 1 d .
N3 N 0.09927(13) 0.03751(12) 0.81537(10) 0.0417(4) Uani 1 1 d .
H3A H 0.0905 0.0155 0.8569 0.050 Uiso 1 1 calc R
O1 O 0.06026(14) 0.06312(11) 1.05819(10) 0.0564(5) Uani 1 1 d .
O2 O 0.09838(12) 0.14799(10) 0.75382(10) 0.0487(4) Uani 1 1 d .
C1 C 0.09085(14) 0.15435(12) 0.88637(12) 0.0356(5) Uani 1 1 d .
C2 C 0.08833(17) 0.09328(13) 1.00234(13) 0.0423(5) Uani 1 1 d .
C3 C 0.17470(17) 0.11358(14) 0.98595(14) 0.0448(6) Uani 1 1 d .
C4 C 0.2466(2) 0.10017(19) 1.02622(17) 0.0612(8) Uani 1 1 d .
H4 H 0.2449 0.0765 1.0719 0.073 Uiso 1 1 calc R
C5 C 0.3202(2) 0.1234(2) 0.9955(2) 0.0698(9) Uani 1 1 d .
H5 H 0.3692 0.1151 1.0210 0.084 Uiso 1 1 calc R
C6 C 0.32275(19) 0.1588(2) 0.9277(2) 0.0670(8) Uani 1 1 d .
H6 H 0.3734 0.1732 0.9081 0.080 Uiso 1 1 calc R
C7 C 0.25114(17) 0.17327(16) 0.88830(17) 0.0511(6) Uani 1 1 d .
H7 H 0.2528 0.1979 0.8431 0.061 Uiso 1 1 calc R
C8 C 0.17751(15) 0.14990(13) 0.91832(13) 0.0399(5) Uani 1 1 d .
C9 C 0.06236(14) 0.23463(13) 0.87856(12) 0.0363(5) Uani 1 1 d .
C10 C 0.09046(16) 0.29663(14) 0.91477(14) 0.0441(5) Uani 1 1 d .
H10 H 0.1357 0.2985 0.9463 0.053 Uiso 1 1 calc R
C11 C 0.03829(15) 0.35808(14) 0.89577(15) 0.0456(5) Uani 1 1 d .
C12 C 0.0351(2) 0.43502(16) 0.9139(2) 0.0649(8) Uani 1 1 d .
H12 H 0.0732 0.4554 0.9466 0.078 Uiso 1 1 calc R
C13 C -0.0239(2) 0.47922(17) 0.8835(3) 0.0767(11) Uani 1 1 d .
H13 H -0.0256 0.5302 0.8953 0.092 Uiso 1 1 calc R
C14 C -0.0813(2) 0.4501(2) 0.8355(3) 0.0761(10) Uani 1 1 d .
H14 H -0.1212 0.4821 0.8159 0.091 Uiso 1 1 calc R
C15 C -0.0820(2) 0.3750(2) 0.81515(18) 0.0618(8) Uani 1 1 d .
H15 H -0.1207 0.3560 0.7822 0.074 Uiso 1 1 calc R
C16 C -0.02130(16) 0.32929(14) 0.84671(13) 0.0432(5) Uani 1 1 d .
C17 C -0.04607(16) 0.10420(15) 0.93758(14) 0.0459(6) Uani 1 1 d .
H17A H -0.0601 0.0549 0.9569 0.055 Uiso 1 1 calc R
H17B H -0.0618 0.1051 0.8860 0.055 Uiso 1 1 calc R
C18 C -0.0964(2) 0.16345(19) 0.97872(17) 0.0597(7) Uani 1 1 d .
H18A H -0.0887 0.1571 1.0314 0.072 Uiso 1 1 calc R
H18B H -0.0769 0.2133 0.9654 0.072 Uiso 1 1 calc R
C19 C -0.1866(2) 0.1569(3) 0.9605(3) 0.0977(15) Uani 1 1 d .
H19A H -0.1939 0.1606 0.9081 0.147 Uiso 1 1 calc R
H19B H -0.2164 0.1967 0.9843 0.147 Uiso 1 1 calc R
H19C H -0.2070 0.1092 0.9774 0.147 Uiso 1 1 calc R
C20 C 0.09346(14) 0.11223(13) 0.81150(12) 0.0368(5) Uani 1 1 d .
C21 C 0.12013(16) -0.00819(14) 0.75079(14) 0.0431(5) Uani 1 1 d .
H21 H 0.0805 0.0036 0.7116 0.052 Uiso 1 1 calc R
C22 C 0.2052(2) 0.0084(2) 0.7224(3) 0.0807(11) Uani 1 1 d .
H22A H 0.2454 -0.0011 0.7609 0.097 Uiso 1 1 calc R
H22B H 0.2089 0.0612 0.7088 0.097 Uiso 1 1 calc R
C23 C 0.2253(3) -0.0407(3) 0.6550(3) 0.0990(15) Uani 1 1 d .
H23A H 0.1894 -0.0264 0.6146 0.119 Uiso 1 1 calc R
H23B H 0.2818 -0.0312 0.6399 0.119 Uiso 1 1 calc R
C24 C 0.2150(3) -0.1223(3) 0.6700(3) 0.0920(14) Uani 1 1 d .
H24A H 0.2570 -0.1385 0.7047 0.110 Uiso 1 1 calc R
H24B H 0.2228 -0.1503 0.6247 0.110 Uiso 1 1 calc R
C25 C 0.1315(3) -0.1395(2) 0.7008(2) 0.0827(12) Uani 1 1 d .
H25A H 0.1290 -0.1924 0.7141 0.099 Uiso 1 1 calc R
H25B H 0.0900 -0.1303 0.6633 0.099 Uiso 1 1 calc R
C26 C 0.1122(3) -0.09135(17) 0.76914(17) 0.0670(9) Uani 1 1 d .
H26A H 0.0566 -0.1019 0.7860 0.080 Uiso 1 1 calc R
H26B H 0.1502 -0.1041 0.8086 0.080 Uiso 1 1 calc R
O1S O 0.5006(9) 0.1749(6) 0.7062(5) 0.265(4) Uani 1 1 d U
C1S C 0.4063(11) 0.1625(9) 0.6992(9) 0.258(6) Uani 1 1 d U
H1S1 H 0.3960 0.1202 0.6675 0.387 Uiso 1 1 d R
H1S2 H 0.3826 0.2070 0.6778 0.387 Uiso 1 1 d R
H1S3 H 0.3818 0.1534 0.7465 0.387 Uiso 1 1 d R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_3
C2 N1 C17 123.7(2) .
C2 N1 C1 113.5(2) .
C17 N1 C1 122.62(19) .
C16 N2 C9 108.5(2) .
C20 N3 C21 121.7(2) .
C20 N3 H3A 119.1 .
C21 N3 H3A 119.1 .
N1 C1 C9 111.17(18) .
N1 C1 C8 101.43(18) .
C9 C1 C8 111.60(19) .
N1 C1 C20 113.05(18) .
C9 C1 C20 112.49(17) .
C8 C1 C20 106.48(18) .
O1 C2 N1 124.9(3) .
O1 C2 C3 128.4(2) .
N1 C2 C3 106.7(2) .
C8 C3 C4 121.0(3) .
C8 C3 C2 108.8(2) .
C4 C3 C2 130.1(3) .
C5 C4 C3 117.3(3) .
C5 C4 H4 121.3 .
C3 C4 H4 121.3 .
C4 C5 C6 121.4(3) .
C4 C5 H5 119.3 .
C6 C5 H5 119.3 .
C5 C6 C7 121.2(3) .
C5 C6 H6 119.4 .
C7 C6 H6 119.4 .
C8 C7 C6 117.7(3) .
C8 C7 H7 121.1 .
C6 C7 H7 121.1 .
C7 C8 C3 121.3(2) .
C7 C8 C1 129.3(2) .
C3 C8 C1 109.3(2) .
C10 C9 N2 109.2(2) .
C10 C9 C1 128.2(2) .
N2 C9 C1 122.1(2) .
C9 C10 C11 107.8(2) .
C9 C10 H10 126.1 .
C11 C10 H10 126.1 .
C12 C11 C16 118.4(3) .
C12 C11 C10 135.3(3) .
C16 C11 C10 106.4(2) .
C13 C12 C11 119.6(3) .
C13 C12 H12 120.2 .
C11 C12 H12 120.2 .
C12 C13 C14 121.2(3) .
C12 C13 H13 119.4 .
C14 C13 H13 119.4 .
C13 C14 C15 122.4(3) .
C13 C14 H14 118.8 .
C15 C14 H14 118.8 .
C14 C15 C16 116.5(3) .
C14 C15 H15 121.8 .
C16 C15 H15 121.8 .
N2 C16 C15 129.9(3) .
N2 C16 C11 108.1(2) .
C15 C16 C11 122.0(3) .
N1 C17 C18 114.3(2) .
N1 C17 H17A 108.7 .
C18 C17 H17A 108.7 .
N1 C17 H17B 108.7 .
C18 C17 H17B 108.7 .
H17A C17 H17B 107.6 .
C19 C18 C17 111.0(3) .
C19 C18 H18A 109.4 .
C17 C18 H18A 109.4 .
C19 C18 H18B 109.4 .
C17 C18 H18B 109.4 .
H18A C18 H18B 108.0 .
C18 C19 H19A 109.5 .
C18 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C18 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
O2 C20 N3 123.8(2) .
O2 C20 C1 119.96(19) .
N3 C20 C1 115.85(18) .
N3 C21 C22 112.2(2) .
N3 C21 C26 110.1(2) .
C22 C21 C26 110.1(3) .
N3 C21 H21 108.1 .
C22 C21 H21 108.1 .
C26 C21 H21 108.1 .
C21 C22 C23 110.9(3) .
C21 C22 H22A 109.5 .
C23 C22 H22A 109.5 .
C21 C22 H22B 109.5 .
C23 C22 H22B 109.5 .
H22A C22 H22B 108.1 .
C24 C23 C22 112.6(4) .
C24 C23 H23A 109.1 .
C22 C23 H23A 109.1 .
C24 C23 H23B 109.1 .
C22 C23 H23B 109.1 .
H23A C23 H23B 107.8 .
C23 C24 C25 111.7(3) .
C23 C24 H24A 109.3 .
C25 C24 H24A 109.3 .
C23 C24 H24B 109.3 .
C25 C24 H24B 109.3 .
H24A C24 H24B 107.9 .
C24 C25 C26 111.8(4) .
C24 C25 H25A 109.3 .
C26 C25 H25A 109.3 .
C24 C25 H25B 109.3 .
C26 C25 H25B 109.3 .
H25A C25 H25B 107.9 .
C21 C26 C25 110.3(3) .
C21 C26 H26A 109.6 .
C25 C26 H26A 109.6 .
C21 C26 H26B 109.6 .
C25 C26 H26B 109.6 .
H26A C26 H26B 108.1 .
C1S O1S O1S 94.0(13) 3_656
O1S C1S H1S1 109.4 .
O1S C1S H1S2 108.0 .
H1S1 C1S H1S2 109.5 .
O1S C1S H1S3 110.9 .
H1S1 C1S H1S3 109.5 .
H1S2 C1S H1S3 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.361(3) .
N1 C17 1.453(3) .
N1 C1 1.470(3) .
N2 C16 1.371(3) .
N2 C9 1.382(3) .
N3 C20 1.332(3) .
N3 C21 1.465(3) .
N3 H3A 0.8600 .
O1 C2 1.233(3) .
O2 C20 1.227(3) .
C1 C9 1.505(3) .
C1 C8 1.521(3) .
C1 C20 1.551(3) .
C2 C3 1.475(4) .
C3 C8 1.387(3) .
C3 C4 1.395(4) .
C4 C5 1.380(5) .
C4 H4 0.9300 .
C5 C6 1.382(6) .
C5 H5 0.9300 .
C6 C7 1.387(4) .
C6 H6 0.9300 .
C7 C8 1.375(4) .
C7 H7 0.9300 .
C9 C10 1.361(3) .
C10 C11 1.423(4) .
C10 H10 0.9300 .
C11 C12 1.407(4) .
C11 C16 1.409(4) .
C12 C13 1.354(5) .
C12 H12 0.9300 .
C13 C14 1.376(6) .
C13 H13 0.9300 .
C14 C15 1.384(5) .
C14 H14 0.9300 .
C15 C16 1.397(4) .
C15 H15 0.9300 .
C17 C18 1.526(4) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.502(5) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C21 C22 1.501(4) .
C21 C26 1.519(4) .
C21 H21 0.9800 .
C22 C23 1.536(6) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C23 C24 1.484(7) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C24 C25 1.495(7) .
C24 H24A 0.9700 .
C24 H24B 0.9700 .
C25 C26 1.539(4) .
C25 H25A 0.9700 .
C25 H25B 0.9700 .
C26 H26A 0.9700 .
C26 H26B 0.9700 .
O1S C1S 1.55(2) .
O1S O1S 1.589(17) 3_656
C1S H1S1 0.9600 .
C1S H1S2 0.9600 .
C1S H1S3 0.9600 .
