#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/60/2226099.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_2226099
loop_
_publ_author_name
'Liu, Yun'
'Jiang, Hong'
_publ_section_title
;
 Phenyl(pyrrolo[2,1-a]isoquinolin-3-yl)methanone
;
_journal_coeditor_code           DS2027
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1376
_journal_paper_doi               10.1107/S1600536810017101
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H13 N O'
_chemical_formula_moiety         'C19 H13 N O'
_chemical_formula_sum            'C19 H13 N O'
_chemical_formula_weight         271.30
_chemical_melting_point          413
_chemical_name_systematic
;
Phenyl(pyrrolo[2,1-a]isoquinolin-3-yl)methanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 101.02(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.637(6)
_cell_length_b                   4.0400(8)
_cell_length_c                   11.824(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1342.7(5)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2351
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.45
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.295
_refine_ls_abs_structure_details '(XCAD4; Harms & Wocadlo, 1995)'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1299
_refine_ls_R_factor_gt           0.0717
_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)+(0.0150P)²+2.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1393
_reflns_number_gt                1388
_reflns_number_total             2351
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ds2027.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226099
_cod_database_fobs_code          2226099
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N N 0.22455(9) 0.5534(7) 0.9319(2) 0.0382(7) Uani d . 1 . .
C C11 0.19331(11) 0.4146(9) 0.9955(3) 0.0402(9) Uani d . 1 . .
C C7 0.31218(12) 0.5686(10) 0.9370(3) 0.0485(10) Uani d . 1 . .
O O 0.30873(9) 0.6625(9) 0.8377(2) 0.0725(10) Uani d . 1 . .
C C12 0.14286(12) 0.4449(10) 0.9532(3) 0.0447(9) Uani d . 1 . .
C C3 0.36071(11) 0.5108(10) 1.0092(3) 0.0453(9) Uani d . 1 . .
C C8 0.27112(11) 0.4828(9) 0.9873(3) 0.0402(9) Uani d . 1 . .
C C19 0.20843(12) 0.7328(10) 0.8334(3) 0.0461(9) Uani d . 1 . .
H H19A 0.2302 0.8309 0.7947 0.055 Uiso calc R 1 . .
C C18 0.16185(12) 0.7680(10) 0.7927(3) 0.0513(10) Uani d . 1 . .
H H18A 0.1517 0.8929 0.7265 0.062 Uiso calc R 1 . .
C C2 0.37259(12) 0.6034(10) 1.1233(3) 0.0521(10) Uani d . 1 . .
H H2A 0.3496 0.6935 1.1600 0.062 Uiso calc R 1 . .
C C17 0.12699(12) 0.6158(10) 0.8496(3) 0.0483(10) Uani d . 1 . .
C C9 0.26796(12) 0.3050(10) 1.0848(3) 0.0458(9) Uani d . 1 . .
H H9A 0.2936 0.2284 1.1389 0.055 Uiso calc R 1 . .
C C10 0.22029(12) 0.2579(10) 1.0897(3) 0.0477(10) Uani d . 1 . .
H H10A 0.2086 0.1416 1.1462 0.057 Uiso calc R 1 . .
C C13 0.10950(12) 0.3043(10) 1.0117(3) 0.0528(10) Uani d . 1 . .
H H13A 0.1197 0.1878 1.0798 0.063 Uiso calc R 1 . .
C C14 0.06138(14) 0.3388(13) 0.9681(4) 0.0706(14) Uani d . 1 . .
H H14A 0.0393 0.2498 1.0080 0.085 Uiso calc R 1 . .
C C16 0.07802(13) 0.6403(12) 0.8072(3) 0.0628(12) Uani d . 1 . .
H H16A 0.0672 0.7509 0.7382 0.075 Uiso calc R 1 . .
C C6 0.45267(14) 0.4265(12) 1.1284(4) 0.0711(13) Uani d . 1 . .
H H6A 0.4837 0.3990 1.1684 0.085 Uiso calc R 1 . .
C C15 0.04577(15) 0.5046(13) 0.8655(4) 0.0711(14) Uani d . 1 . .
H H15A 0.0134 0.5238 0.8361 0.085 Uiso calc R 1 . .
C C4 0.39519(13) 0.3782(11) 0.9543(3) 0.0567(11) Uani d . 1 . .
H H4A 0.3875 0.3207 0.8769 0.068 Uiso calc R 1 . .
C C5 0.44071(14) 0.3323(12) 1.0152(4) 0.0684(13) Uani d . 1 . .
H H5A 0.4635 0.2365 0.9792 0.082 Uiso calc R 1 . .
C C1 0.41862(13) 0.5626(12) 1.1833(3) 0.0650(12) Uani d . 1 . .
H H1A 0.4267 0.6263 1.2602 0.078 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C19 N C11 . . 121.6(3) yes
C19 N C8 . . 129.8(3) yes
C11 N C8 . . 108.5(3) yes
C10 C11 N . . 107.6(3) yes
C10 C11 C12 . . 133.4(3) ?
N C11 C12 . . 118.9(3) ?
O C7 C8 . . 123.0(3) yes
O C7 C3 . . 119.4(3) yes
C8 C7 C3 . . 117.4(3) ?
C13 C12 C17 . . 119.5(3) ?
C13 C12 C11 . . 121.8(3) ?
C17 C12 C11 . . 118.7(3) ?
C2 C3 C4 . . 119.8(3) ?
C2 C3 C7 . . 122.8(3) ?
C4 C3 C7 . . 117.2(3) ?
C9 C8 N . . 106.9(3) ?
C9 C8 C7 . . 130.8(3) ?
N C8 C7 . . 122.1(3) ?
C18 C19 N . . 120.8(3) ?
C18 C19 H19A . . 119.6 ?
N C19 H19A . . 119.6 ?
C19 C18 C17 . . 121.2(3) ?
C19 C18 H18A . . 119.4 ?
C17 C18 H18A . . 119.4 ?
C3 C2 C1 . . 120.2(4) ?
C3 C2 H2A . . 119.9 ?
C1 C2 H2A . . 119.9 ?
C16 C17 C12 . . 118.8(4) ?
C16 C17 C18 . . 122.5(4) ?
C12 C17 C18 . . 118.6(3) ?
C8 C9 C10 . . 109.2(3) ?
C8 C9 H9A . . 125.4 ?
C10 C9 H9A . . 125.4 ?
C11 C10 C9 . . 107.8(3) ?
C11 C10 H10A . . 126.1 ?
C9 C10 H10A . . 126.1 ?
C14 C13 C12 . . 120.0(4) ?
C14 C13 H13A . . 120.0 ?
C12 C13 H13A . . 120.0 ?
C13 C14 C15 . . 120.5(4) ?
C13 C14 H14A . . 119.7 ?
C15 C14 H14A . . 119.7 ?
C15 C16 C17 . . 121.2(4) ?
C15 C16 H16A . . 119.4 ?
C17 C16 H16A . . 119.4 ?
C5 C6 C1 . . 120.1(4) ?
C5 C6 H6A . . 119.9 ?
C1 C6 H6A . . 119.9 ?
C16 C15 C14 . . 120.0(4) ?
C16 C15 H15A . . 120.0 ?
C14 C15 H15A . . 120.0 ?
C5 C4 C3 . . 119.7(4) ?
C5 C4 H4A . . 120.2 ?
C3 C4 H4A . . 120.2 ?
C6 C5 C4 . . 120.5(4) ?
C6 C5 H5A . . 119.7 ?
C4 C5 H5A . . 119.7 ?
C6 C1 C2 . . 119.6(4) ?
C6 C1 H1A . . 120.2 ?
C2 C1 H1A . . 120.2 ?
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
N C19 . 1.374(4) yes
N C11 . 1.392(4) yes
N C8 . 1.399(4) yes
C11 C10 . 1.382(5) ?
C11 C12 . 1.441(4) ?
C7 O . 1.220(4) yes
C7 C8 . 1.458(4) yes
C7 C3 . 1.504(5) ?
C12 C13 . 1.402(5) ?
C12 C17 . 1.404(5) ?
C3 C2 . 1.379(5) ?
C3 C4 . 1.388(4) ?
C8 C9 . 1.376(4) ?
C19 C18 . 1.336(4) ?
C19 H19A . 0.9300 ?
C18 C17 . 1.444(5) ?
C18 H18A . 0.9300 ?
C2 C1 . 1.382(5) ?
C2 H2A . 0.9300 ?
C17 C16 . 1.399(5) ?
C9 C10 . 1.390(4) ?
C9 H9A . 0.9300 ?
C10 H10A . 0.9300 ?
C13 C14 . 1.383(5) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.383(6) ?
C14 H14A . 0.9300 ?
C16 C15 . 1.368(6) ?
C16 H16A . 0.9300 ?
C6 C5 . 1.371(5) ?
C6 C1 . 1.385(5) ?
C6 H6A . 0.9300 ?
C15 H15A . 0.9300 ?
C4 C5 . 1.376(5) ?
C4 H4A . 0.9300 ?
C5 H5A . 0.9300 ?
C1 H1A . 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
C19 H19A O . 0.93 2.31 2.875(4) 119 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C19 N C11 C10 . . . . -178.7(3) ?
C8 N C11 C10 . . . . -0.2(4) ?
C19 N C11 C12 . . . . 3.5(5) ?
C8 N C11 C12 . . . . -178.0(3) ?
C10 C11 C12 C13 . . . . 1.4(7) ?
N C11 C12 C13 . . . . 178.5(3) ?
C10 C11 C12 C17 . . . . -177.5(4) ?
N C11 C12 C17 . . . . -0.4(5) ?
O C7 C3 C2 . . . . 138.8(4) ?
C8 C7 C3 C2 . . . . -46.0(6) ?
O C7 C3 C4 . . . . -36.8(6) ?
C8 C7 C3 C4 . . . . 138.3(4) ?
C19 N C8 C9 . . . . 177.8(3) ?
C11 N C8 C9 . . . . -0.6(4) ?
C19 N C8 C7 . . . . -7.2(6) ?
C11 N C8 C7 . . . . 174.4(3) ?
O C7 C8 C9 . . . . 162.9(4) ?
C3 C7 C8 C9 . . . . -12.1(6) ?
O C7 C8 N . . . . -10.8(6) ?
C3 C7 C8 N . . . . 174.2(3) ?
C11 N C19 C18 . . . . -2.9(5) ?
C8 N C19 C18 . . . . 178.9(4) ?
N C19 C18 C17 . . . . -0.8(6) ?
C4 C3 C2 C1 . . . . -0.4(6) ?
C7 C3 C2 C1 . . . . -175.9(4) ?
C13 C12 C17 C16 . . . . -0.1(6) ?
C11 C12 C17 C16 . . . . 178.8(4) ?
C13 C12 C17 C18 . . . . 178.0(4) ?
C11 C12 C17 C18 . . . . -3.0(5) ?
C19 C18 C17 C16 . . . . -178.2(4) ?
C19 C18 C17 C12 . . . . 3.8(6) ?
N C8 C9 C10 . . . . 1.2(4) ?
C7 C8 C9 C10 . . . . -173.2(4) ?
N C11 C10 C9 . . . . 0.9(4) ?
C12 C11 C10 C9 . . . . 178.2(4) ?
C8 C9 C10 C11 . . . . -1.3(5) ?
C17 C12 C13 C14 . . . . -1.0(6) ?
C11 C12 C13 C14 . . . . -179.9(4) ?
C12 C13 C14 C15 . . . . 1.6(7) ?
C12 C17 C16 C15 . . . . 0.7(6) ?
C18 C17 C16 C15 . . . . -177.3(4) ?
C17 C16 C15 C14 . . . . -0.2(7) ?
C13 C14 C15 C16 . . . . -1.0(7) ?
C2 C3 C4 C5 . . . . 1.7(6) ?
C7 C3 C4 C5 . . . . 177.5(4) ?
C1 C6 C5 C4 . . . . 1.4(7) ?
C3 C4 C5 C6 . . . . -2.2(7) ?
C5 C6 C1 C2 . . . . -0.1(7) ?
C3 C2 C1 C6 . . . . -0.4(7) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745065
