#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/53/2225358.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_2225358
loop_
_publ_author_name
'Safarov, Saifidin'
'Voskressensky, Leonid G.'
'Bizhko, Oksana V.'
'Kulikova, Larisa N.'
'Khrustalev, Victor N.'
_publ_section_title
;
 8H-Chromeno[2',3':4,5]imidazo[2,1-a]isoquinoline
;
_journal_coeditor_code           RK2193
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o710
_journal_paper_doi               10.1107/S1600536810006744
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H12 N2 O'
_chemical_formula_moiety         'C18 H12 N2 O'
_chemical_formula_sum            'C18 H12 N2 O'
_chemical_formula_weight         272.30
_chemical_name_systematic
;
8H-Chromeno[2',3':4,5]imidazo[2,1-a]isoquinoline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.682(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9717(15)
_cell_length_b                   6.0580(8)
_cell_length_c                   17.948(2)
_cell_measurement_reflns_used    1700
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2.3
_cell_volume                     1269.9(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.056
_diffrn_reflns_av_sigmaI/netI    0.047
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12413
_diffrn_reflns_theta_full        27.0
_diffrn_reflns_theta_max         27.0
_diffrn_reflns_theta_min         1.9
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.00
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.00
_refine_ls_R_factor_all          0.105
_refine_ls_R_factor_gt           0.066
_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)+(0.077P)²+1.7P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.154
_refine_ls_wR_factor_ref         0.182
_reflns_number_gt                1821
_reflns_number_total             2734
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2193.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2225358
_cod_database_fobs_code          2225358
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C C1 0.6165(2) 0.1766(5) -0.07577(16) 0.0290(6) Uani d . 1 . .
H H1 0.5719 0.0665 -0.0583 0.035 Uiso calc R 1 . .
C C2 0.6436(2) 0.1563(5) -0.14599(17) 0.0349(7) Uani d . 1 . .
H H2 0.6185 0.0302 -0.1766 0.042 Uiso calc R 1 . .
C C3 0.7068(2) 0.3167(6) -0.17271(17) 0.0372(7) Uani d . 1 . .
H H3 0.7237 0.3008 -0.2217 0.045 Uiso calc R 1 . .
C C4 0.7447(2) 0.4957(5) -0.12988(17) 0.0349(7) Uani d . 1 . .
H H4 0.7885 0.6033 -0.1494 0.042 Uiso calc R 1 . .
C C4A 0.7213(2) 0.5276(5) -0.05755(16) 0.0309(6) Uani d . 1 . .
C C5 0.7591(2) 0.7182(5) -0.01180(16) 0.0332(7) Uani d . 1 . .
H H5 0.8052 0.8253 -0.0295 0.040 Uiso calc R 1 . .
C C6 0.7306(2) 0.7478(5) 0.05559(16) 0.0310(6) Uani d . 1 . .
H H6 0.7538 0.8777 0.0845 0.037 Uiso calc R 1 . .
N N7 0.66701(19) 0.5884(4) 0.08314(13) 0.0269(5) Uani d . 1 . .
C C7A 0.6332(2) 0.5823(4) 0.15238(15) 0.0251(6) Uani d . 1 . .
C C8 0.6498(2) 0.7432(5) 0.21381(16) 0.0326(7) Uani d . 1 . .
H H8A 0.6141 0.8858 0.1950 0.039 Uiso calc R 1 . .
H H8B 0.7325 0.7676 0.2349 0.039 Uiso calc R 1 . .
C C8A 0.5921(2) 0.6458(5) 0.27520(16) 0.0301(6) Uani d . 1 . .
C C9 0.5902(2) 0.7644(5) 0.34032(18) 0.0347(7) Uani d . 1 . .
H H9 0.6261 0.9050 0.3466 0.042 Uiso calc R 1 . .
C C10 0.5385(3) 0.6886(5) 0.39654(18) 0.0382(7) Uani d . 1 . .
H H10 0.5390 0.7752 0.4407 0.046 Uiso calc R 1 . .
C C11 0.4851(2) 0.4809(6) 0.38774(18) 0.0387(8) Uani d . 1 . .
H H11 0.4483 0.4261 0.4258 0.046 Uiso calc R 1 . .
C C12 0.4864(2) 0.3558(5) 0.32275(16) 0.0304(6) Uani d . 1 . .
H H12 0.4516 0.2141 0.3163 0.037 Uiso calc R 1 . .
C C12A 0.5393(2) 0.4417(5) 0.26757(15) 0.0264(6) Uani d . 1 . .
O O13 0.53167(16) 0.2981(3) 0.20489(11) 0.0319(5) Uani d . 1 . .
C C13A 0.5786(2) 0.3795(5) 0.14856(15) 0.0297(6) Uani d . 1 . .
N N14 0.57698(19) 0.2676(4) 0.08385(13) 0.0297(5) Uani d . 1 . .
C C14A 0.6311(2) 0.3960(5) 0.04379(16) 0.0291(6) Uani d . 1 . .
C C14B 0.6554(2) 0.3618(5) -0.02983(14) 0.0278(6) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C14B . . 119.6(3) ?
C2 C1 H1 . . 120.2 ?
C14B C1 H1 . . 120.2 ?
C1 C2 C3 . . 120.9(3) ?
C1 C2 H2 . . 119.6 ?
C3 C2 H2 . . 119.6 ?
C4 C3 C2 . . 120.6(3) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C4A . . 121.9(3) ?
C3 C4 H4 . . 119.0 ?
C4A C4 H4 . . 119.0 ?
C4 C4A C5 . . 122.7(3) ?
C4 C4A C14B . . 117.6(3) ?
C5 C4A C14B . . 119.7(3) ?
C6 C5 C4A . . 121.0(3) ?
C6 C5 H5 . . 119.5 ?
C4A C5 H5 . . 119.5 ?
C5 C6 N7 . . 119.9(3) ?
C5 C6 H6 . . 120.1 ?
N7 C6 H6 . . 120.1 ?
C14A N7 C6 . . 122.6(2) ?
C14A N7 C7A . . 108.4(2) ?
C6 N7 C7A . . 129.0(2) ?
C13A C7A N7 . . 101.9(2) ?
C13A C7A C8 . . 128.1(2) ?
N7 C7A C8 . . 130.0(2) ?
C7A C8 C8A . . 106.1(2) ?
C7A C8 H8A . . 110.5 ?
C8A C8 H8A . . 110.5 ?
C7A C8 H8B . . 110.5 ?
C8A C8 H8B . . 110.5 ?
H8A C8 H8B . . 108.7 ?
C9 C8A C12A . . 117.3(3) ?
C9 C8A C8 . . 120.1(3) ?
C12A C8A C8 . . 122.6(3) ?
C10 C9 C8A . . 122.9(3) ?
C10 C9 H9 . . 118.5 ?
C8A C9 H9 . . 118.5 ?
C9 C10 C11 . . 119.0(3) ?
C9 C10 H10 . . 120.5 ?
C11 C10 H10 . . 120.5 ?
C12 C11 C10 . . 119.5(3) ?
C12 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
C12A C12 C11 . . 118.9(3) ?
C12A C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
C8A C12A C12 . . 122.4(3) ?
C8A C12A O13 . . 125.4(2) ?
C12 C12A O13 . . 112.2(2) ?
C13A O13 C12A . . 114.0(2) ?
N14 C13A O13 . . 122.2(3) ?
N14 C13A C7A . . 114.1(2) ?
O13 C13A C7A . . 123.7(2) ?
C14A N14 C13A . . 104.9(2) ?
N14 C14A N7 . . 110.7(2) ?
N14 C14A C14B . . 129.9(3) ?
N7 C14A C14B . . 119.4(3) ?
C1 C14B C14A . . 123.3(3) ?
C1 C14B C4A . . 119.4(2) ?
C14A C14B C4A . . 117.3(3) ?
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
C1 C2 . 1.374(4) ?
C1 C14B . 1.410(4) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.380(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.349(5) ?
C3 H3 . 0.9500 ?
C4 C4A . 1.400(4) ?
C4 H4 . 0.9500 ?
C4A C5 . 1.432(4) ?
C4A C14B . 1.432(4) ?
C5 C6 . 1.339(4) ?
C5 H5 . 0.9500 ?
C6 N7 . 1.386(4) ?
C6 H6 . 0.9500 ?
N7 C14A . 1.382(4) ?
N7 C7A . 1.390(4) ?
C7A C13A . 1.386(4) ?
C7A C8 . 1.452(4) ?
C8 C8A . 1.540(4) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C8A C9 . 1.377(4) ?
C8A C12A . 1.382(4) ?
C9 C10 . 1.373(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.405(5) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.394(4) ?
C11 H11 . 0.9500 ?
C12 C12A . 1.389(4) ?
C12 H12 . 0.9500 ?
C12A O13 . 1.409(3) ?
O13 C13A . 1.353(3) ?
C13A N14 . 1.341(4) ?
N14 C14A . 1.321(4) ?
C14A C14B . 1.429(4) ?
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
C8 H8A O13 1_565 0.99 2.71 3.637(4) 157 yes
C8 H8B Cg 2_655 0.99 2.63 3.547(3) 154 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
C14B C1 C2 C3 . . . . -1.1(4) ?
C1 C2 C3 C4 . . . . 0.9(4) ?
C2 C3 C4 C4A . . . . -0.5(4) ?
C3 C4 C4A C5 . . . . -178.9(3) ?
C3 C4 C4A C14B . . . . 0.2(4) ?
C4 C4A C5 C6 . . . . 176.9(3) ?
C14B C4A C5 C6 . . . . -2.3(4) ?
C4A C5 C6 N7 . . . . 2.4(4) ?
C5 C6 N7 C14A . . . . 0.2(4) ?
C5 C6 N7 C7A . . . . 176.8(3) ?
C14A N7 C7A C13A . . . . 0.3(3) ?
C6 N7 C7A C13A . . . . -176.7(3) ?
C14A N7 C7A C8 . . . . -179.9(3) ?
C6 N7 C7A C8 . . . . 3.1(5) ?
C13A C7A C8 C8A . . . . -1.0(4) ?
N7 C7A C8 C8A . . . . 179.3(2) ?
C7A C8 C8A C9 . . . . -177.9(2) ?
C7A C8 C8A C12A . . . . 1.0(4) ?
C12A C8A C9 C10 . . . . -0.1(4) ?
C8 C8A C9 C10 . . . . 178.9(3) ?
C8A C9 C10 C11 . . . . 0.0(4) ?
C9 C10 C11 C12 . . . . 0.6(4) ?
C10 C11 C12 C12A . . . . -1.0(4) ?
C9 C8A C12A C12 . . . . -0.4(4) ?
C8 C8A C12A C12 . . . . -179.3(2) ?
C9 C8A C12A O13 . . . . 179.4(2) ?
C8 C8A C12A O13 . . . . 0.5(4) ?
C11 C12 C12A C8A . . . . 0.9(4) ?
C11 C12 C12A O13 . . . . -178.9(2) ?
C8A C12A O13 C13A . . . . -2.1(4) ?
C12 C12A O13 C13A . . . . 177.7(2) ?
C12A O13 C13A N14 . . . . -178.5(2) ?
C12A O13 C13A C7A . . . . 2.1(4) ?
N7 C7A C13A N14 . . . . -0.3(3) ?
C8 C7A C13A N14 . . . . 180.0(3) ?
N7 C7A C13A O13 . . . . 179.1(2) ?
C8 C7A C13A O13 . . . . -0.6(4) ?
O13 C13A N14 C14A . . . . -179.3(2) ?
C7A C13A N14 C14A . . . . 0.1(3) ?
C13A N14 C14A N7 . . . . 0.1(3) ?
C13A N14 C14A C14B . . . . 179.9(3) ?
C6 N7 C14A N14 . . . . 177.0(2) ?
C7A N7 C14A N14 . . . . -0.3(3) ?
C6 N7 C14A C14B . . . . -2.8(4) ?
C7A N7 C14A C14B . . . . 179.9(2) ?
C2 C1 C14B C14A . . . . 179.9(3) ?
C2 C1 C14B C4A . . . . 0.8(4) ?
N14 C14A C14B C1 . . . . 3.9(4) ?
N7 C14A C14B C1 . . . . -176.3(2) ?
N14 C14A C14B C4A . . . . -176.9(3) ?
N7 C14A C14B C4A . . . . 2.8(4) ?
C4 C4A C14B C1 . . . . -0.4(4) ?
C5 C4A C14B C1 . . . . 178.8(2) ?
C4 C4A C14B C14A . . . . -179.5(2) ?
C5 C4A C14B C14A . . . . -0.4(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744561
