#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/19/2211999.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_2211999
loop_
_publ_author_name
'Yun Liu'
'Zhe Li'
'Yong-Miao Shen'
'Ye Zhang'
'Jian-Hua Xu'
_publ_section_title
;Ethyl
 7-oxo-7H-indeno[2',1':3,4]pyrrolo[2,1-a]quinoline-12-carboxylate
;
_journal_coeditor_code           AT2201
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o759
_journal_page_last               o760
_journal_paper_doi               10.1107/S1600536807001183
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C22 H15 N O3'
_chemical_formula_moiety         'C22 H15 N O3'
_chemical_formula_sum            'C22 H15 N O3'
_chemical_formula_weight         341.35
_chemical_melting_point          466
_chemical_name_systematic
;
Ethyl 7-oxo-7H-indeno[2',1':3,4]pyrrolo[2,1-a]quinoline-12-carboxylate
;
_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
_cell_angle_alpha                99.33(3)
_cell_angle_beta                 98.15(3)
_cell_angle_gamma                108.13(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5210(15)
_cell_length_b                   9.4560(19)
_cell_length_c                   12.411(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.50
_cell_measurement_theta_min      2.38
_cell_volume                     810.2(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      288(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3086
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9725
_exptl_absorpt_correction_T_min  0.8715
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.184
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0520
_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)+(0.057P)²+0.2168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                1941
_reflns_number_total             2847
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2201.cif
_cod_data_source_block           I
_cod_database_code               2211999
_cod_database_fobs_code          2211999
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O O1 0.2088(2) 0.17891(17) 0.21912(13) 0.0420(4) Uani d . 1
O O2 0.2428(3) 0.18223(19) 0.04241(14) 0.0561(5) Uani d . 1
O O3 0.5318(3) 0.92222(19) 0.19536(15) 0.0628(6) Uani d . 1
N N 0.5239(3) 0.47353(19) 0.28823(14) 0.0317(5) Uani d . 1
C C22 0.0383(6) -0.0381(4) 0.2799(3) 0.0945(13) Uani d . 1
H H22A -0.0413 -0.1435 0.2572 0.142 Uiso calc R 1
H H22B -0.0294 0.0196 0.3165 0.142 Uiso calc R 1
H H22C 0.1527 -0.0283 0.3304 0.142 Uiso calc R 1
C C21 0.0880(4) 0.0191(3) 0.1827(2) 0.0565(8) Uani d . 1
H H21A -0.0270 0.0092 0.1310 0.068 Uiso calc R 1
H H21B 0.1556 -0.0392 0.1449 0.068 Uiso calc R 1
C C20 0.2826(3) 0.2441(3) 0.13975(19) 0.0374(6) Uani d . 1
C C12 0.4034(3) 0.4040(2) 0.18111(17) 0.0319(5) Uani d . 1
C C11 0.3900(3) 0.5201(2) 0.13131(17) 0.0328(5) Uani d . 1
C C15 0.2928(3) 0.5481(3) 0.02935(18) 0.0346(6) Uani d . 1
C C16 0.1751(3) 0.4519(3) -0.06762(19) 0.0431(6) Uani d . 1
H H16A 0.1424 0.3467 -0.0778 0.052 Uiso calc R 1
C C17 0.1067(4) 0.5171(3) -0.1497(2) 0.0490(7) Uani d . 1
H H17A 0.0270 0.4539 -0.2156 0.059 Uiso calc R 1
C C18 0.1538(4) 0.6721(3) -0.1358(2) 0.0536(7) Uani d . 1
H H18A 0.1060 0.7122 -0.1924 0.064 Uiso calc R 1
C C19 0.2717(4) 0.7700(3) -0.0386(2) 0.0494(7) Uani d . 1
H H19A 0.3039 0.8751 -0.0291 0.059 Uiso calc R 1
C C14 0.3399(3) 0.7065(3) 0.04379(19) 0.0400(6) Uani d . 1
C C13 0.4685(4) 0.7855(3) 0.1565(2) 0.0418(6) Uani d . 1
C C10 0.4925(3) 0.6605(2) 0.20523(18) 0.0357(6) Uani d . 1
C C9 0.5751(3) 0.6312(2) 0.30277(18) 0.0341(5) Uani d . 1
C C8 0.6846(3) 0.7266(3) 0.40635(19) 0.0403(6) Uani d . 1
H H8A 0.7144 0.8317 0.4178 0.048 Uiso calc R 1
C C7 0.7454(3) 0.6647(3) 0.4883(2) 0.0432(6) Uani d . 1
H H7A 0.8101 0.7269 0.5578 0.052 Uiso calc R 1
C C4 0.7117(3) 0.5046(3) 0.46972(18) 0.0371(6) Uani d . 1
C C3 0.7878(4) 0.4407(3) 0.5507(2) 0.0479(7) Uani d . 1
H H3A 0.8536 0.5024 0.6202 0.057 Uiso calc R 1
C C2 0.7678(4) 0.2904(3) 0.5303(2) 0.0553(7) Uani d . 1
H H2A 0.8161 0.2492 0.5859 0.066 Uiso calc R 1
C C1 0.6750(4) 0.1989(3) 0.4258(2) 0.0508(7) Uani d . 1
H H1A 0.6654 0.0969 0.4110 0.061 Uiso calc R 1
C C6 0.5968(3) 0.2565(3) 0.3437(2) 0.0393(6) Uani d . 1
H H6A 0.5370 0.1944 0.2735 0.047 Uiso calc R 1
C C5 0.6074(3) 0.4074(2) 0.36606(17) 0.0326(5) Uani d . 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 0.0016 '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
_geom_angle_publ_flag
C20 O1 C21 115.55(18) ?
C9 N C5 121.21(18) ?
C9 N C12 108.63(18) ?
C5 N C12 129.63(18) ?
C21 C22 H22A 109.5 ?
C21 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
C21 C22 H22C 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
C22 C21 O1 108.5(2) ?
C22 C21 H21A 110.0 ?
O1 C21 H21A 110.0 ?
C22 C21 H21B 110.0 ?
O1 C21 H21B 110.0 ?
H21A C21 H21B 108.4 ?
O2 C20 O1 124.0(2) ?
O2 C20 C12 122.6(2) yes
O1 C20 C12 113.20(19) ?
C11 C12 N 106.53(18) ?
C11 C12 C20 124.6(2) ?
N C12 C20 127.6(2) yes
C12 C11 C10 109.56(19) ?
C12 C11 C15 141.4(2) ?
C10 C11 C15 108.83(19) ?
C16 C15 C14 120.4(2) ?
C16 C15 C11 132.6(2) ?
C14 C15 C11 107.0(2) ?
C15 C16 C17 118.0(2) ?
C15 C16 H16A 121.0 ?
C17 C16 H16A 121.0 ?
C18 C17 C16 121.6(2) ?
C18 C17 H17A 119.2 ?
C16 C17 H17A 119.2 ?
C17 C18 C19 120.9(2) ?
C17 C18 H18A 119.5 ?
C19 C18 H18A 119.5 ?
C14 C19 C18 118.0(3) ?
C14 C19 H19A 121.0 ?
C18 C19 H19A 121.0 ?
C19 C14 C15 121.2(2) ?
C19 C14 C13 128.9(2) ?
C15 C14 C13 110.0(2) ?
O3 C13 C10 129.8(2) ?
O3 C13 C14 126.4(2) ?
C10 C13 C14 103.8(2) ?
C9 C10 C11 107.89(19) ?
C9 C10 C13 141.7(2) ?
C11 C10 C13 110.3(2) ?
C10 C9 N 107.34(19) ?
C10 C9 C8 133.0(2) ?
N C9 C8 119.6(2) ?
C7 C8 C9 119.9(2) ?
C7 C8 H8A 120.1 ?
C9 C8 H8A 120.1 ?
C8 C7 C4 120.8(2) ?
C8 C7 H7A 119.6 ?
C4 C7 H7A 119.6 ?
C3 C4 C5 118.1(2) ?
C3 C4 C7 121.4(2) ?
C5 C4 C7 120.4(2) ?
C2 C3 C4 121.4(2) ?
C2 C3 H3A 119.3 ?
C4 C3 H3A 119.3 ?
C3 C2 C1 119.5(2) ?
C3 C2 H2A 120.2 ?
C1 C2 H2A 120.2 ?
C6 C1 C2 121.1(2) ?
C6 C1 H1A 119.5 ?
C2 C1 H1A 119.5 ?
C1 C6 C5 119.6(2) ?
C1 C6 H6A 120.2 ?
C5 C6 H6A 120.2 ?
C6 C5 N 123.2(2) ?
C6 C5 C4 120.0(2) ?
N C5 C4 116.8(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C20 1.341(3) ?
O1 C21 1.456(3) ?
O2 C20 1.204(3) yes
O3 C13 1.216(3) ?
N C9 1.393(3) ?
N C5 1.410(3) ?
N C12 1.423(3) yes
C22 C21 1.450(4) ?
C22 H22A 0.9600 ?
C22 H22B 0.9600 ?
C22 H22C 0.9600 ?
C21 H21A 0.9700 ?
C21 H21B 0.9700 ?
C20 C12 1.462(3) ?
C12 C11 1.367(3) ?
C11 C10 1.403(3) ?
C11 C15 1.474(3) ?
C15 C16 1.379(3) ?
C15 C14 1.402(3) ?
C16 C17 1.390(3) ?
C16 H16A 0.9300 ?
C17 C18 1.372(4) ?
C17 H17A 0.9300 ?
C18 C19 1.386(4) ?
C18 H18A 0.9300 ?
C19 C14 1.383(3) ?
C19 H19A 0.9300 ?
C14 C13 1.510(3) ?
C13 C10 1.459(3) ?
C10 C9 1.390(3) ?
C9 C8 1.416(3) ?
C8 C7 1.347(3) ?
C8 H8A 0.9300 ?
C7 C4 1.429(3) ?
C7 H7A 0.9300 ?
C4 C3 1.397(3) ?
C4 C5 1.413(3) ?
C3 C2 1.359(4) ?
C3 H3A 0.9300 ?
C2 C1 1.386(4) ?
C2 H2A 0.9300 ?
C1 C6 1.375(3) ?
C1 H1A 0.9300 ?
C6 C5 1.383(3) ?
C6 H6A 0.9300 ?
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
_geom_hbond_publ_flag
C6 H6A O1 . 0.93 2.42 2.909(3) 113 yes
C6 H6A O3 1_545 0.93 2.58 3.243(3) 128 yes
C16 H16A O2 . 0.93 2.52 3.220(3) 132 yes
C21 H21A O2 2_555 0.97 2.54 3.313(3) 136 yes
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_publ_flag
C20 O1 C21 C22 173.6(3) ?
C21 O1 C20 O2 5.8(4) yes
C21 O1 C20 C12 -179.7(2) ?
C9 N C12 C11 2.3(2) ?
C5 N C12 C11 -169.2(2) ?
C9 N C12 C20 -165.3(2) ?
C5 N C12 C20 23.2(4) ?
O2 C20 C12 C11 42.9(4) ?
O1 C20 C12 C11 -131.6(2) ?
O2 C20 C12 N -151.6(2) ?
O1 C20 C12 N 33.9(3) ?
N C12 C11 C10 -2.2(3) ?
C20 C12 C11 C10 165.9(2) ?
N C12 C11 C15 -175.9(3) ?
C20 C12 C11 C15 -7.8(5) ?
C12 C11 C15 C16 -5.9(5) ?
C10 C11 C15 C16 -179.7(2) ?
C12 C11 C15 C14 174.0(3) ?
C10 C11 C15 C14 0.3(3) ?
C14 C15 C16 C17 0.4(3) ?
C11 C15 C16 C17 -179.7(2) ?
C15 C16 C17 C18 0.0(4) ?
C16 C17 C18 C19 -0.2(4) ?
C17 C18 C19 C14 -0.1(4) ?
C18 C19 C14 C15 0.5(4) ?
C18 C19 C14 C13 -179.8(2) ?
C16 C15 C14 C19 -0.7(4) ?
C11 C15 C14 C19 179.3(2) ?
C16 C15 C14 C13 179.6(2) ?
C11 C15 C14 C13 -0.4(3) ?
C19 C14 C13 O3 1.8(4) ?
C15 C14 C13 O3 -178.6(2) ?
C19 C14 C13 C10 -179.4(2) ?
C15 C14 C13 C10 0.3(3) ?
C12 C11 C10 C9 1.2(3) ?
C15 C11 C10 C9 177.10(19) ?
C12 C11 C10 C13 -175.9(2) ?
C15 C11 C10 C13 -0.1(3) ?
O3 C13 C10 C9 3.0(5) ?
C14 C13 C10 C9 -175.8(3) ?
O3 C13 C10 C11 178.7(3) ?
C14 C13 C10 C11 -0.1(3) ?
C11 C10 C9 N 0.3(3) ?
C13 C10 C9 N 176.0(3) ?
C11 C10 C9 C8 -176.5(2) ?
C13 C10 C9 C8 -0.7(5) ?
C5 N C9 C10 170.78(19) ?
C12 N C9 C10 -1.6(2) ?
C5 N C9 C8 -12.0(3) ?
C12 N C9 C8 175.7(2) ?
C10 C9 C8 C7 179.3(3) ?
N C9 C8 C7 2.9(4) ?
C9 C8 C7 C4 4.2(4) ?
C8 C7 C4 C3 174.5(2) ?
C8 C7 C4 C5 -2.4(4) ?
C5 C4 C3 C2 1.9(4) ?
C7 C4 C3 C2 -175.1(2) ?
C4 C3 C2 C1 1.9(4) ?
C3 C2 C1 C6 -2.3(4) yes
C2 C1 C6 C5 -1.3(4) ?
C1 C6 C5 N -177.2(2) ?
C1 C6 C5 C4 5.2(4) ?
C9 N C5 C6 -164.3(2) ?
C12 N C5 C6 6.2(4) ?
C9 N C5 C4 13.4(3) yes
C12 N C5 C4 -176.0(2) ?
C3 C4 C5 C6 -5.4(3) ?
C7 C4 C5 C6 171.6(2) ?
C3 C4 C5 N 176.7(2) ?
C7 C4 C5 N -6.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125537
