#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/10/7151064.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_7151064
loop_
_publ_author_name
'Chen, Wei'
'Du, Wei'
'Yue, Lei'
'Li, Rui'
'Wu, Yong'
'Ding, Li-Sheng'
'Chen, Ying-Chun'
_publ_section_title
;
 Organocatalytic enantioselective indole alkylations of
 alpha,beta-unsaturated ketones.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              816
_journal_page_last               821
_journal_paper_doi               10.1039/b616504d
_journal_volume                  5
_journal_year                    2007
_chemical_formula_sum            'C20 H20 Cl N O2'
_chemical_formula_weight         341.82
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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            4
_cell_length_a                   5.1480(1)
_cell_length_b                   15.8080(3)
_cell_length_c                   21.3073(5)
_cell_measurement_reflns_used    16793
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.15
_cell_volume                     1733.98(6)
_computing_cell_refinement       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_collection       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_reduction        'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17187
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.9638
_exptl_absorpt_correction_T_min  0.8831
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_coef       0.0117(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0296
_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)+(0.0429P)²+0.4980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0782
_reflns_number_gt                3914
_reflns_number_total             3985
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b616504d.txt
_cod_data_source_block           4bh
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7151064
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Cl Cl 0.83456(11) 0.19448(2) 0.34804(2) 0.05003(14) Uani 1 1 d . . .
O1 O 0.3698(2) 0.62837(7) 0.29070(5) 0.0334(2) Uani 1 1 d . . .
O2 O 0.5009(2) 0.56043(6) 0.63379(5) 0.0306(2) Uani 1 1 d . . .
N N 1.0710(2) 0.69158(7) 0.47872(6) 0.0277(2) Uani 1 1 d . . .
C1 C 0.9087(3) 0.68491(8) 0.42780(6) 0.0232(3) Uani 1 1 d . . .
C2 C 0.8857(3) 0.73581(8) 0.37437(7) 0.0296(3) Uani 1 1 d . . .
H2 H 0.9934 0.7840 0.3686 0.035 Uiso 1 1 calc R . .
C3 C 0.7020(3) 0.71380(8) 0.33057(6) 0.0304(3) Uani 1 1 d . . .
H3 H 0.6834 0.7471 0.2937 0.036 Uiso 1 1 calc R . .
C4 C 0.5400(3) 0.64257(8) 0.33917(6) 0.0246(3) Uani 1 1 d . . .
C5 C 0.5608(2) 0.59237(8) 0.39193(6) 0.0206(2) Uani 1 1 d . . .
H5 H 0.4505 0.5448 0.3977 0.025 Uiso 1 1 calc R . .
C6 C 0.7498(2) 0.61353(7) 0.43692(6) 0.0188(2) Uani 1 1 d . . .
C7 C 0.8294(2) 0.57493(7) 0.49493(5) 0.0200(2) Uani 1 1 d . . .
C8 C 1.0279(3) 0.62371(8) 0.51799(6) 0.0250(3) Uani 1 1 d . . .
H8 H 1.1218 0.6124 0.5555 0.030 Uiso 1 1 calc R . .
C9 C 0.1880(3) 0.56195(10) 0.29842(6) 0.0308(3) Uani 1 1 d . . .
H9A H 0.0859 0.5718 0.3365 0.037 Uiso 1 1 calc R . .
H9B H 0.2806 0.5080 0.3021 0.037 Uiso 1 1 calc R . .
H9C H 0.0719 0.5601 0.2620 0.037 Uiso 1 1 calc R . .
C10 C 0.7186(2) 0.49468(7) 0.52147(5) 0.0193(2) Uani 1 1 d . . .
H10 H 0.5274 0.5036 0.5264 0.023 Uiso 1 1 calc R . .
C11 C 0.7550(2) 0.41934(7) 0.47781(5) 0.0197(2) Uani 1 1 d . . .
C12 C 0.9594(3) 0.41431(8) 0.43527(6) 0.0250(3) Uani 1 1 d . . .
H12 H 1.0824 0.4590 0.4332 0.030 Uiso 1 1 calc R . .
C13 C 0.9867(3) 0.34486(9) 0.39572(6) 0.0291(3) Uani 1 1 d . . .
H13 H 1.1268 0.3421 0.3668 0.035 Uiso 1 1 calc R . .
C14 C 0.8077(3) 0.28017(8) 0.39910(6) 0.0298(3) Uani 1 1 d . . .
C15 C 0.6043(3) 0.28262(9) 0.44108(7) 0.0322(3) Uani 1 1 d . . .
H15 H 0.4831 0.2374 0.4432 0.039 Uiso 1 1 calc R . .
C16 C 0.5795(3) 0.35232(8) 0.48022(7) 0.0273(3) Uani 1 1 d . . .
H16 H 0.4397 0.3544 0.5093 0.033 Uiso 1 1 calc R . .
C17 C 0.8279(3) 0.47443(8) 0.58699(6) 0.0233(2) Uani 1 1 d . . .
H17A H 0.7876 0.4148 0.5975 0.028 Uiso 1 1 calc R . .
H17B H 1.0192 0.4806 0.5861 0.028 Uiso 1 1 calc R . .
C18 C 0.7179(2) 0.53150(8) 0.63781(5) 0.0220(2) Uani 1 1 d . . .
C19 C 0.8859(3) 0.54562(11) 0.69415(6) 0.0346(3) Uani 1 1 d . . .
H19A H 1.0547 0.5688 0.6800 0.041 Uiso 1 1 calc R . .
H19B H 0.9205 0.4902 0.7142 0.041 Uiso 1 1 calc R . .
C20 C 0.7726(3) 0.60491(11) 0.74314(7) 0.0388(4) Uani 1 1 d . . .
H20A H 0.5979 0.5858 0.7546 0.047 Uiso 1 1 calc R . .
H20B H 0.7632 0.6623 0.7259 0.047 Uiso 1 1 calc R . .
H20C H 0.8837 0.6049 0.7805 0.047 Uiso 1 1 calc R . .
H0N H 1.206(4) 0.7268(13) 0.4834(9) 0.048(5) Uiso 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'
Cl Cl 0.1484 0.1585 '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
C4 O1 C9 117.11(10) . . ?
C1 N C8 108.77(11) . . ?
C1 N H0N 127.4(13) . . ?
C8 N H0N 122.8(13) . . ?
N C1 C2 130.57(12) . . ?
N C1 C6 107.83(11) . . ?
C2 C1 C6 121.60(12) . . ?
C3 C2 C1 117.76(12) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.34(12) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
O1 C4 C5 124.63(12) . . ?
O1 C4 C3 114.17(11) . . ?
C5 C4 C3 121.19(12) . . ?
C4 C5 C6 118.18(11) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C5 C6 C1 119.93(11) . . ?
C5 C6 C7 133.02(11) . . ?
C1 C6 C7 107.04(11) . . ?
C8 C7 C6 106.37(11) . . ?
C8 C7 C10 128.56(11) . . ?
C6 C7 C10 125.02(11) . . ?
C7 C8 N 109.88(11) . . ?
C7 C8 H8 125.1 . . ?
N C8 H8 125.1 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 C11 112.58(10) . . ?
C7 C10 C17 112.24(10) . . ?
C11 C10 C17 110.27(9) . . ?
C7 C10 H10 107.1 . . ?
C11 C10 H10 107.1 . . ?
C17 C10 H10 107.1 . . ?
C12 C11 C16 118.10(12) . . ?
C12 C11 C10 122.40(11) . . ?
C16 C11 C10 119.49(11) . . ?
C13 C12 C11 121.08(12) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 119.10(13) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 121.41(12) . . ?
C15 C14 Cl 119.16(11) . . ?
C13 C14 Cl 119.41(12) . . ?
C14 C15 C16 118.84(13) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C11 121.46(13) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C18 C17 C10 112.77(10) . . ?
C18 C17 H17A 109.0 . . ?
C10 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C10 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
O2 C18 C19 122.29(12) . . ?
O2 C18 C17 121.20(12) . . ?
C19 C18 C17 116.42(11) . . ?
C18 C19 C20 114.91(13) . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19B 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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
Cl C14 1.7428(13) . ?
O1 C4 1.3726(17) . ?
O1 C9 1.4159(18) . ?
O2 C18 1.2102(17) . ?
N C1 1.3734(18) . ?
N C8 1.3786(18) . ?
N H0N 0.89(2) . ?
C1 C2 1.3991(18) . ?
C1 C6 1.4074(17) . ?
C2 C3 1.373(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.4131(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3802(17) . ?
C5 C6 1.4062(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4381(16) . ?
C7 C8 1.3712(17) . ?
C7 C10 1.5015(16) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.5228(16) . ?
C10 C17 1.5387(16) . ?
C10 H10 1.0000 . ?
C11 C12 1.3911(18) . ?
C11 C16 1.3936(17) . ?
C12 C13 1.3911(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.5190(17) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.4964(18) . ?
C19 C20 1.519(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N H0N N 0.89(2) 2.42(2) 3.2954(14) 166.2(18) 4_566
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N C1 C2 -177.33(13) . . . . ?
C8 N C1 C6 3.19(14) . . . . ?
N C1 C2 C3 -179.55(13) . . . . ?
C6 C1 C2 C3 -0.14(19) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C9 O1 C4 C5 5.96(19) . . . . ?
C9 O1 C4 C3 -175.23(11) . . . . ?
C2 C3 C4 O1 -178.97(12) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
O1 C4 C5 C6 178.19(12) . . . . ?
C3 C4 C5 C6 -0.54(19) . . . . ?
C4 C5 C6 C1 0.85(17) . . . . ?
C4 C5 C6 C7 -177.70(12) . . . . ?
N C1 C6 C5 179.02(11) . . . . ?
C2 C1 C6 C5 -0.52(18) . . . . ?
N C1 C6 C7 -2.10(13) . . . . ?
C2 C1 C6 C7 178.37(11) . . . . ?
C5 C6 C7 C8 178.91(13) . . . . ?
C1 C6 C7 C8 0.23(13) . . . . ?
C5 C6 C7 C10 1.4(2) . . . . ?
C1 C6 C7 C10 -177.30(11) . . . . ?
C6 C7 C8 N 1.74(14) . . . . ?
C10 C7 C8 N 179.15(12) . . . . ?
C1 N C8 C7 -3.12(15) . . . . ?
C8 C7 C10 C11 -116.99(14) . . . . ?
C6 C7 C10 C11 59.98(15) . . . . ?
C8 C7 C10 C17 8.15(17) . . . . ?
C6 C7 C10 C17 -174.89(11) . . . . ?
C7 C10 C11 C12 27.70(16) . . . . ?
C17 C10 C11 C12 -98.51(14) . . . . ?
C7 C10 C11 C16 -152.60(11) . . . . ?
C17 C10 C11 C16 81.20(14) . . . . ?
C16 C11 C12 C13 0.67(19) . . . . ?
C10 C11 C12 C13 -179.62(11) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C12 C13 C14 Cl 178.00(10) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
Cl C14 C15 C16 -177.97(11) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
C12 C11 C16 C15 -0.64(19) . . . . ?
C10 C11 C16 C15 179.64(12) . . . . ?
C7 C10 C17 C18 73.80(14) . . . . ?
C11 C10 C17 C18 -159.81(11) . . . . ?
C10 C17 C18 O2 30.32(17) . . . . ?
C10 C17 C18 C19 -153.02(12) . . . . ?
O2 C18 C19 C20 -5.0(2) . . . . ?
C17 C18 C19 C20 178.41(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17267063
2 PubChem 16109675
