#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/20/2222021.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222021
loop_
_publ_author_name
'Li, Peifan'
'Wang, Wenjie'
'Li, Caiyun'
'Bian, Xiaoxia'
_publ_section_title
;
 Ethyl 2-benzyl-1-propyl-1H-indole-3-carboxylate
;
_journal_coeditor_code           HB2963
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1284
_journal_paper_doi               10.1107/S1600536809016493
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C21 H23 N O2'
_chemical_formula_sum            'C21 H23 N O2'
_chemical_formula_weight         321.40
_chemical_name_systematic
;
Ethyl 2-benzyl-1-propyl-1H-indole-3-carboxylate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.231(3)
_cell_length_b                   19.479(4)
_cell_length_c                   5.5226(11)
_cell_measurement_reflns_used    5126
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.491
_cell_measurement_theta_min      2.439
_cell_volume                     1746.0(6)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            13765
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_correction_T_min  0.9846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.154
_refine_ls_abs_structure_details 'None, Friedel Pairs merged'
_refine_ls_extinction_coef       0.044(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0435
_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)+(0.0496P)²+0.3147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2060
_reflns_number_total             2204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            hb2963.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2222021
_cod_database_fobs_code          2222021
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.38761(9) 0.34048(8) 0.2851(4) 0.0430(5) Uani d . 1 . .
O O2 0.45086(8) 0.40505(7) 0.0042(3) 0.0357(4) Uani d . 1 . .
N N1 0.62712(10) 0.24714(8) 0.3130(4) 0.0294(4) Uani d . 1 . .
C C1 0.66004(12) 0.28279(10) 0.1183(4) 0.0300(5) Uani d . 1 . .
C C2 0.73763(13) 0.27623(11) 0.0133(5) 0.0355(5) Uani d . 1 . .
H H2 0.7768 0.2440 0.0718 0.043 Uiso calc R 1 . .
C C3 0.75495(13) 0.31898(11) -0.1805(5) 0.0392(6) Uani d . 1 . .
H H3 0.8075 0.3164 -0.2557 0.047 Uiso calc R 1 . .
C C4 0.69695(14) 0.36590(11) -0.2680(5) 0.0383(6) Uani d . 1 . .
H H4 0.7107 0.3941 -0.4023 0.046 Uiso calc R 1 . .
C C5 0.62019(13) 0.37209(10) -0.1635(5) 0.0339(5) Uani d . 1 . .
H H5 0.5813 0.4042 -0.2245 0.041 Uiso calc R 1 . .
C C6 0.60052(12) 0.33007(10) 0.0348(4) 0.0288(4) Uani d . 1 . .
C C7 0.52909(13) 0.32030(9) 0.1883(4) 0.0288(5) Uani d . 1 . .
C C8 0.54835(12) 0.26987(10) 0.3565(5) 0.0290(4) Uani d . 1 . .
C C9 0.67057(12) 0.19227(10) 0.4394(5) 0.0326(5) Uani d . 1 . .
H H9A 0.6472 0.1873 0.6041 0.039 Uiso calc R 1 . .
H H9B 0.7293 0.2052 0.4568 0.039 Uiso calc R 1 . .
C C10 0.66510(12) 0.12335(10) 0.3092(5) 0.0336(5) Uani d . 1 . .
H H10A 0.6066 0.1103 0.2890 0.040 Uiso calc R 1 . .
H H10B 0.6901 0.1273 0.1464 0.040 Uiso calc R 1 . .
C C11 0.70976(14) 0.06838(11) 0.4534(5) 0.0404(6) Uani d . 1 . .
H H11A 0.7673 0.0821 0.4774 0.061 Uiso calc R 1 . .
H H11B 0.7079 0.0248 0.3647 0.061 Uiso calc R 1 . .
H H11C 0.6830 0.0627 0.6112 0.061 Uiso calc R 1 . .
C C12 0.49933(13) 0.24338(10) 0.5656(4) 0.0315(5) Uani d . 1 . .
H H12A 0.4530 0.2753 0.5963 0.038 Uiso calc R 1 . .
H H12B 0.5348 0.2433 0.7115 0.038 Uiso calc R 1 . .
C C13 0.46466(12) 0.17145(10) 0.5295(4) 0.0271(4) Uani d . 1 . .
C C14 0.47834(13) 0.12068(10) 0.7011(4) 0.0317(5) Uani d . 1 . .
H H14 0.5121 0.1302 0.8376 0.038 Uiso calc R 1 . .
C C15 0.44300(14) 0.05585(11) 0.6750(5) 0.0360(5) Uani d . 1 . .
H H15 0.4527 0.0214 0.7933 0.043 Uiso calc R 1 . .
C C16 0.39379(13) 0.04180(11) 0.4763(5) 0.0350(5) Uani d . 1 . .
H H16 0.3692 -0.0022 0.4589 0.042 Uiso calc R 1 . .
C C17 0.38041(13) 0.09212(10) 0.3027(5) 0.0331(5) Uani d . 1 . .
H H17 0.3470 0.0825 0.1656 0.040 Uiso calc R 1 . .
C C18 0.41579(12) 0.15656(10) 0.3295(4) 0.0296(4) Uani d . 1 . .
H H18 0.4065 0.1908 0.2100 0.036 Uiso calc R 1 . .
C C19 0.44951(13) 0.35436(10) 0.1705(4) 0.0308(5) Uani d . 1 . .
C C20 0.37460(14) 0.44182(11) -0.0340(6) 0.0410(6) Uani d . 1 . .
H H20A 0.3565 0.4641 0.1180 0.049 Uiso calc R 1 . .
H H20B 0.3308 0.4099 -0.0879 0.049 Uiso calc R 1 . .
C C21 0.39091(15) 0.49475(12) -0.2251(5) 0.0442(6) Uani d . 1 . .
H H21A 0.4351 0.5254 -0.1710 0.066 Uiso calc R 1 . .
H H21B 0.3407 0.5215 -0.2539 0.066 Uiso calc R 1 . .
H H21C 0.4076 0.4719 -0.3755 0.066 Uiso calc R 1 . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C19 O2 C20 . . 116.62(17) ?
C8 N1 C1 . . 109.44(18) ?
C8 N1 C9 . . 127.0(2) ?
C1 N1 C9 . . 123.49(17) ?
N1 C1 C2 . . 128.7(2) ?
N1 C1 C6 . . 108.43(17) ?
C2 C1 C6 . . 122.9(2) ?
C3 C2 C1 . . 116.8(2) ?
C3 C2 H2 . . 121.6 ?
C1 C2 H2 . . 121.6 ?
C2 C3 C4 . . 121.6(2) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C5 C4 C3 . . 121.4(2) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
C4 C5 C6 . . 118.8(2) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C5 C6 C1 . . 118.65(19) ?
C5 C6 C7 . . 135.6(2) ?
C1 C6 C7 . . 105.70(19) ?
C8 C7 C6 . . 107.73(18) ?
C8 C7 C19 . . 124.58(19) ?
C6 C7 C19 . . 127.7(2) ?
N1 C8 C7 . . 108.7(2) ?
N1 C8 C12 . . 121.3(2) ?
C7 C8 C12 . . 129.92(19) ?
N1 C9 C10 . . 113.02(19) ?
N1 C9 H9A . . 109.0 ?
C10 C9 H9A . . 109.0 ?
N1 C9 H9B . . 109.0 ?
C10 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
C11 C10 C9 . . 110.2(2) ?
C11 C10 H10A . . 109.6 ?
C9 C10 H10A . . 109.6 ?
C11 C10 H10B . . 109.6 ?
C9 C10 H10B . . 109.6 ?
H10A C10 H10B . . 108.1 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C8 C12 C13 . . 114.42(18) ?
C8 C12 H12A . . 108.7 ?
C13 C12 H12A . . 108.7 ?
C8 C12 H12B . . 108.7 ?
C13 C12 H12B . . 108.7 ?
H12A C12 H12B . . 107.6 ?
C14 C13 C18 . . 119.03(18) ?
C14 C13 C12 . . 120.5(2) ?
C18 C13 C12 . . 120.43(19) ?
C13 C14 C15 . . 120.6(2) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C16 C15 C14 . . 119.9(2) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C15 C16 C17 . . 119.9(2) ?
C15 C16 H16 . . 120.1 ?
C17 C16 H16 . . 120.1 ?
C18 C17 C16 . . 120.0(2) ?
C18 C17 H17 . . 120.0 ?
C16 C17 H17 . . 120.0 ?
C17 C18 C13 . . 120.6(2) ?
C17 C18 H18 . . 119.7 ?
C13 C18 H18 . . 119.7 ?
O1 C19 O2 . . 121.99(19) ?
O1 C19 C7 . . 126.6(2) ?
O2 C19 C7 . . 111.41(18) ?
O2 C20 C21 . . 106.99(19) ?
O2 C20 H20A . . 110.3 ?
C21 C20 H20A . . 110.3 ?
O2 C20 H20B . . 110.3 ?
C21 C20 H20B . . 110.3 ?
H20A C20 H20B . . 108.6 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C19 . 1.218(3) ?
O2 C19 . 1.349(3) ?
O2 C20 . 1.446(3) ?
N1 C8 . 1.374(3) ?
N1 C1 . 1.387(3) ?
N1 C9 . 1.458(3) ?
C1 C2 . 1.392(3) ?
C1 C6 . 1.412(3) ?
C2 C3 . 1.385(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.398(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.378(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.404(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.449(3) ?
C7 C8 . 1.388(3) ?
C7 C19 . 1.455(3) ?
C8 C12 . 1.494(3) ?
C9 C10 . 1.526(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.518(3) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 C13 . 1.523(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.387(3) ?
C13 C18 . 1.391(3) ?
C14 C15 . 1.394(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.384(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.388(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.388(3) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C20 C21 . 1.499(4) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2 O1 3_555 0.95 2.708 3.653(3) 173
C9 H9B O1 3_555 0.99 2.880 3.680(3) 138
C11 H11A O1 3_555 0.98 2.686 3.514(3) 142
C12 H12A O1 . 0.99 2.386 3.044(3) 123
C18 H18 O1 . 0.95 2.961 3.620(3) 128
C21 H21A O2 2_664 0.98 2.912 3.555(3) 124
C3 H3 Cg 3_554 0.95 2.82 3.632(3) 144
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N1 C1 C2 . . . . -180.0(2) ?
C9 N1 C1 C2 . . . . -2.4(3) ?
C8 N1 C1 C6 . . . . 0.2(2) ?
C9 N1 C1 C6 . . . . 177.74(19) ?
N1 C1 C2 C3 . . . . -179.6(2) ?
C6 C1 C2 C3 . . . . 0.2(3) ?
C1 C2 C3 C4 . . . . -0.7(3) ?
C2 C3 C4 C5 . . . . 0.6(4) ?
C3 C4 C5 C6 . . . . -0.1(3) ?
C4 C5 C6 C1 . . . . -0.4(3) ?
C4 C5 C6 C7 . . . . -179.1(2) ?
N1 C1 C6 C5 . . . . -179.83(18) ?
C2 C1 C6 C5 . . . . 0.3(3) ?
N1 C1 C6 C7 . . . . -0.8(2) ?
C2 C1 C6 C7 . . . . 179.4(2) ?
C5 C6 C7 C8 . . . . 179.9(2) ?
C1 C6 C7 C8 . . . . 1.1(2) ?
C5 C6 C7 C19 . . . . 1.8(4) ?
C1 C6 C7 C19 . . . . -177.0(2) ?
C1 N1 C8 C7 . . . . 0.5(2) ?
C9 N1 C8 C7 . . . . -176.92(19) ?
C1 N1 C8 C12 . . . . -176.43(18) ?
C9 N1 C8 C12 . . . . 6.1(3) ?
C6 C7 C8 N1 . . . . -1.0(2) ?
C19 C7 C8 N1 . . . . 177.15(19) ?
C6 C7 C8 C12 . . . . 175.6(2) ?
C19 C7 C8 C12 . . . . -6.3(4) ?
C8 N1 C9 C10 . . . . 96.0(3) ?
C1 N1 C9 C10 . . . . -81.1(2) ?
N1 C9 C10 C11 . . . . -178.64(18) ?
N1 C8 C12 C13 . . . . -75.8(3) ?
C7 C8 C12 C13 . . . . 107.9(2) ?
C8 C12 C13 C14 . . . . 127.6(2) ?
C8 C12 C13 C18 . . . . -55.3(3) ?
C18 C13 C14 C15 . . . . -0.6(3) ?
C12 C13 C14 C15 . . . . 176.5(2) ?
C13 C14 C15 C16 . . . . 0.0(3) ?
C14 C15 C16 C17 . . . . 0.6(3) ?
C15 C16 C17 C18 . . . . -0.5(3) ?
C16 C17 C18 C13 . . . . -0.1(3) ?
C14 C13 C18 C17 . . . . 0.7(3) ?
C12 C13 C18 C17 . . . . -176.49(19) ?
C20 O2 C19 O1 . . . . -0.7(3) ?
C20 O2 C19 C7 . . . . 178.6(2) ?
C8 C7 C19 O1 . . . . -5.9(4) ?
C6 C7 C19 O1 . . . . 171.8(2) ?
C8 C7 C19 O2 . . . . 174.8(2) ?
C6 C7 C19 O2 . . . . -7.5(3) ?
C19 O2 C20 C21 . . . . -179.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742309
2 PubChem 71421576
