#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/97/2209732.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_2209732
loop_
_publ_author_name
'Wei Wang'
_publ_section_title
;
 Diethyl pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate
;
_journal_coeditor_code           AT2056
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3376
_journal_page_last               o3377
_journal_paper_doi               10.1107/S1600536806026663
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H17 N O4'
_chemical_formula_moiety         'C18 H17 N O4'
_chemical_formula_sum            'C18 H17 N O4'
_chemical_formula_weight         311.33
_chemical_melting_point          120.0
_chemical_name_systematic
;
Diethyl pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate
;
_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                92.27(3)
_cell_angle_beta                 98.09(3)
_cell_angle_gamma                109.42(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5960(15)
_cell_length_b                   9.920(2)
_cell_length_c                   11.451(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      1.8
_cell_volume                     802.2(3)
_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      297(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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3046
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9731
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.386
_refine_ls_extinction_coef       0.058(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0548
_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)+(0.0708P)²+0.3401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1490
_reflns_number_gt                2060
_reflns_number_total             2812
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2056.cif
_cod_data_source_block           I
_cod_database_code               2209732
_cod_database_fobs_code          2209732
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
C C1 0.6678(3) 0.8925(2) 0.63017(19) 0.0436(5) Uani d . 1
C C2 0.5761(3) 0.8403(2) 0.51295(19) 0.0441(5) Uani d . 1
C C3 0.6626(3) 0.9369(2) 0.43881(19) 0.0462(6) Uani d . 1
H H3A 0.6309 0.9285 0.3567 0.055 Uiso calc R 1
C C4 0.9238(3) 1.1699(3) 0.4669(2) 0.0513(6) Uani d . 1
H H4A 0.9128 1.1835 0.3866 0.062 Uiso calc R 1
C C5 1.0551(3) 1.2675(3) 0.5444(2) 0.0542(6) Uani d . 1
H H5A 1.1342 1.3496 0.5176 0.065 Uiso calc R 1
C C6 1.0777(3) 1.2493(3) 0.6682(2) 0.0499(6) Uani d . 1
C C7 0.9549(3) 1.1263(2) 0.7104(2) 0.0455(5) Uani d . 1
C C8 0.8111(3) 1.0219(2) 0.62484(18) 0.0425(5) Uani d . 1
C C9 0.9808(4) 1.1107(3) 0.8315(2) 0.0561(6) Uani d . 1
H H9A 0.9015 1.0304 0.8603 0.067 Uiso calc R 1
C C10 1.1211(4) 1.2117(3) 0.9084(2) 0.0681(8) Uani d . 1
H H10A 1.1356 1.1996 0.9889 0.082 Uiso calc R 1
C C11 1.2418(4) 1.3317(3) 0.8674(3) 0.0710(8) Uani d . 1
H H11A 1.3374 1.3996 0.9202 0.085 Uiso calc R 1
C C12 1.2202(4) 1.3505(3) 0.7491(3) 0.0638(7) Uani d . 1
H H12A 1.3012 1.4316 0.7222 0.077 Uiso calc R 1
C C13 0.6163(3) 0.8221(2) 0.7382(2) 0.0490(6) Uani d . 1
C C14 0.4292(3) 0.7000(3) 0.4768(2) 0.0487(6) Uani d . 1
C C15 0.3882(6) 0.7700(4) 0.8670(3) 0.0994(12) Uani d . 1
H H15A 0.3286 0.6671 0.8481 0.119 Uiso calc R 1
H H15B 0.4925 0.7873 0.9317 0.119 Uiso calc R 1
C C16 0.2526(6) 0.8310(6) 0.9012(4) 0.144 Uani d . 1
H H16A 0.2038 0.7868 0.9684 0.216 Uiso calc R 1
H H16B 0.1506 0.8143 0.8364 0.216 Uiso calc R 1
H H16C 0.3134 0.9324 0.9214 0.216 Uiso calc R 1
C C17 0.2389(4) 0.5434(3) 0.3110(2) 0.0633(7) Uani d . 1
H H17A 0.1213 0.5219 0.3423 0.076 Uiso calc R 1
H H17B 0.2930 0.4696 0.3305 0.076 Uiso calc R 1
C C18 0.2040(4) 0.5485(3) 0.1808(3) 0.0782(9) Uani d . 1
H H18A 0.1180 0.4571 0.1444 0.117 Uiso calc R 1
H H18B 0.3213 0.5702 0.1510 0.117 Uiso calc R 1
H H18C 0.1499 0.6215 0.1627 0.117 Uiso calc R 1
N N1 0.8023(2) 1.04708(19) 0.50565(15) 0.0436(5) Uani d . 1
O O1 0.7027(3) 0.7616(2) 0.79706(17) 0.0778(6) Uani d . 1
O O2 0.4576(3) 0.8370(2) 0.76378(16) 0.0705(6) Uani d . 1
O O3 0.3730(3) 0.60962(19) 0.54364(16) 0.0691(5) Uani d . 1
O O4 0.3689(2) 0.68256(17) 0.36088(14) 0.0586(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
C8 C1 C2 107.49(19) ?
C8 C1 C13 126.9(2) ?
C2 C1 C13 125.6(2) ?
C3 C2 C1 107.9(2) ?
C3 C2 C14 126.1(2) ?
C1 C2 C14 125.6(2) ?
N1 C3 C2 108.26(19) ?
N1 C3 H3A 125.9 ?
C2 C3 H3A 125.9 ?
C5 C4 N1 120.0(2) ?
C5 C4 H4A 120.0 ?
N1 C4 H4A 120.0 ?
C4 C5 C6 121.5(2) ?
C4 C5 H5A 119.3 ?
C6 C5 H5A 119.3 ?
C12 C6 C7 119.0(2) ?
C12 C6 C5 121.2(2) ?
C7 C6 C5 119.7(2) ?
C9 C7 C6 118.6(2) ?
C9 C7 C8 123.4(2) ?
C6 C7 C8 118.0(2) ?
C1 C8 N1 106.44(19) ?
C1 C8 C7 135.3(2) ?
N1 C8 C7 118.22(19) ?
C10 C9 C7 121.0(3) ?
C10 C9 H9A 119.5 ?
C7 C9 H9A 119.5 ?
C9 C10 C11 120.5(3) ?
C9 C10 H10A 119.7 ?
C11 C10 H10A 119.7 ?
C12 C11 C10 120.0(3) ?
C12 C11 H11A 120.0 ?
C10 C11 H11A 120.0 ?
C11 C12 C6 120.9(3) ?
C11 C12 H12A 119.6 ?
C6 C12 H12A 119.6 ?
O1 C13 O2 123.0(2) ?
O1 C13 C1 126.3(2) ?
O2 C13 C1 110.68(19) ?
O3 C14 O4 124.0(2) ?
O3 C14 C2 124.4(2) ?
O4 C14 C2 111.6(2) ?
C16 C15 O2 108.4(3) ?
C16 C15 H15A 110.0 ?
O2 C15 H15A 110.0 ?
C16 C15 H15B 110.0 ?
O2 C15 H15B 110.0 ?
H15A C15 H15B 108.4 ?
C15 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C15 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
O4 C17 C18 107.1(2) ?
O4 C17 H17A 110.3 ?
C18 C17 H17A 110.3 ?
O4 C17 H17B 110.3 ?
C18 C17 H17B 110.3 ?
H17A C17 H17B 108.5 ?
C17 C18 H18A 109.5 ?
C17 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C17 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C3 N1 C8 109.89(18) yes
C3 N1 C4 127.65(19) ?
C8 N1 C4 122.5(2) ?
C13 O2 C15 116.5(2) ?
C14 O4 C17 117.54(19) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C8 1.389(3) ?
C1 C2 1.413(3) ?
C1 C13 1.481(3) ?
C2 C3 1.369(3) ?
C2 C14 1.464(3) ?
C3 N1 1.357(3) yes
C3 H3A 0.9300 ?
C4 C5 1.327(3) ?
C4 N1 1.394(3) ?
C4 H4A 0.9300 ?
C5 C6 1.430(3) ?
C5 H5A 0.9300 ?
C6 C12 1.400(4) ?
C6 C7 1.417(3) ?
C7 C9 1.394(3) ?
C7 C8 1.447(3) ?
C8 N1 1.394(3) yes
C9 C10 1.368(4) ?
C9 H9A 0.9300 ?
C10 C11 1.385(4) ?
C10 H10A 0.9300 ?
C11 C12 1.369(4) ?
C11 H11A 0.9300 ?
C12 H12A 0.9300 ?
C13 O1 1.189(3) ?
C13 O2 1.332(3) ?
C14 O3 1.210(3) ?
C14 O4 1.327(3) ?
C15 C16 1.445(5) ?
C15 O2 1.456(3) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
C17 O4 1.442(3) ?
C17 C18 1.483(4) ?
C17 H17A 0.9700 ?
C17 H17B 0.9700 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
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
C5 H5A O3 1_665 0.93 2.59 3.451(3) 154 yes
C10 H10A O1 2_777 0.93 2.53 3.415(3) 157 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
C8 C1 C2 C3 -0.2(2) ?
C13 C1 C2 C3 178.8(2) ?
C8 C1 C2 C14 173.5(2) ?
C13 C1 C2 C14 -7.5(3) ?
C1 C2 C3 N1 -0.6(2) ?
C14 C2 C3 N1 -174.27(19) ?
N1 C4 C5 C6 0.8(4) ?
C4 C5 C6 C12 178.0(2) ?
C4 C5 C6 C7 -1.6(3) ?
C12 C6 C7 C9 0.0(3) ?
C5 C6 C7 C9 179.6(2) ?
C12 C6 C7 C8 -178.8(2) ?
C5 C6 C7 C8 0.8(3) ?
C2 C1 C8 N1 0.9(2) ?
C13 C1 C8 N1 -178.0(2) ?
C2 C1 C8 C7 -179.0(2) ?
C13 C1 C8 C7 2.0(4) ?
C9 C7 C8 C1 1.8(4) ?
C6 C7 C8 C1 -179.4(2) ?
C9 C7 C8 N1 -178.1(2) ?
C6 C7 C8 N1 0.6(3) ?
C6 C7 C9 C10 0.2(4) ?
C8 C7 C9 C10 178.9(2) ?
C7 C9 C10 C11 -0.4(4) ?
C9 C10 C11 C12 0.4(4) ?
C10 C11 C12 C6 -0.3(4) ?
C7 C6 C12 C11 0.1(4) ?
C5 C6 C12 C11 -179.5(2) ?
C8 C1 C13 O1 -74.0(3) ?
C2 C1 C13 O1 107.2(3) ?
C8 C1 C13 O2 104.9(3) yes
C2 C1 C13 O2 -73.8(3) ?
C3 C2 C14 O3 170.1(2) ?
C1 C2 C14 O3 -2.5(4) ?
C3 C2 C14 O4 -8.1(3) ?
C1 C2 C14 O4 179.27(19) yes
C2 C3 N1 C8 1.2(2) ?
C2 C3 N1 C4 -178.79(19) ?
C1 C8 N1 C3 -1.3(2) ?
C7 C8 N1 C3 178.66(18) yes
C1 C8 N1 C4 178.67(19) ?
C7 C8 N1 C4 -1.4(3) ?
C5 C4 N1 C3 -179.4(2) ?
C5 C4 N1 C8 0.6(3) ?
O1 C13 O2 C15 -2.2(4) ?
C1 C13 O2 C15 178.8(2) ?
C16 C15 O2 C13 163.4(3) ?
O3 C14 O4 C17 -4.8(3) ?
C2 C14 O4 C17 173.46(19) ?
C18 C17 O4 C14 -176.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2969849
