#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/35/2223593.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_2223593
loop_
_publ_author_name
'Qin, Jiang-Ke'
'Yang, Zheng-Min'
'Zeng, Ming-Hua'
'Ng, Seik Weng'
_publ_section_title
;
 7H-Chromeno[3,2-h]quinolin-7-one methanol monosolvate
;
_journal_coeditor_code           XU2605
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2368
_journal_paper_doi               10.1107/S160053680903534X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H9 N O2, C H4 O'
_chemical_formula_moiety         'C16 H9 N O2, C H4 O'
_chemical_formula_sum            'C17 H13 N O3'
_chemical_formula_weight         279.28
_chemical_name_systematic
;
7H-Chromeno[3,2-h]quinolin-7-one methanol monosolvate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.172(3)
_cell_angle_beta                 108.760(3)
_cell_angle_gamma                93.532(3)
_cell_formula_units_Z            2
_cell_length_a                   8.102(2)
_cell_length_b                   8.791(3)
_cell_length_c                   10.150(3)
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.2
_cell_volume                     662.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ and ω'
_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  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3838
_diffrn_reflns_theta_full        26.45
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0688P)²+0.0458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1471
_reflns_number_gt                1456
_reflns_number_total             2655
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2605.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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               2223593
_cod_database_fobs_code          2223593
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.25297(18) 0.41753(15) 0.57244(14) 0.0387(4) Uani d . 1 . .
O O2 0.2583(2) 0.64419(19) 0.25985(17) 0.0601(5) Uani d . 1 . .
O O3 0.2226(2) 0.2382(2) 0.8300(2) 0.0735(6) Uani d . 1 . .
H H3 0.1946 0.3170 0.8021 0.110 Uiso calc R 1 . .
N N1 0.1800(2) 0.5518(2) 0.80538(18) 0.0402(5) Uani d . 1 . .
C C1 0.2905(3) 0.3418(2) 0.4545(2) 0.0359(5) Uani d . 1 . .
C C2 0.3238(3) 0.1887(3) 0.4504(2) 0.0449(6) Uani d . 1 . .
H H2 0.3204 0.1427 0.5242 0.054 Uiso calc R 1 . .
C C3 0.3619(3) 0.1058(3) 0.3359(3) 0.0506(6) Uani d . 1 . .
H H3a 0.3839 0.0027 0.3318 0.061 Uiso calc R 1 . .
C C4 0.3680(3) 0.1741(3) 0.2259(3) 0.0535(6) Uani d . 1 . .
H H4 0.3943 0.1169 0.1489 0.064 Uiso calc R 1 . .
C C5 0.3353(3) 0.3254(3) 0.2310(2) 0.0475(6) Uani d . 1 . .
H H5 0.3398 0.3706 0.1570 0.057 Uiso calc R 1 . .
C C6 0.2950(3) 0.4136(2) 0.3461(2) 0.0374(5) Uani d . 1 . .
C C7 0.2553(3) 0.5754(2) 0.3526(2) 0.0401(5) Uani d . 1 . .
C C8 0.2134(2) 0.6488(2) 0.4794(2) 0.0341(5) Uani d . 1 . .
C C9 0.1720(3) 0.8044(2) 0.4991(2) 0.0429(6) Uani d . 1 . .
H H9 0.1653 0.8579 0.4280 0.052 Uiso calc R 1 . .
C C10 0.1423(3) 0.8764(3) 0.6186(3) 0.0445(6) Uani d . 1 . .
H H10 0.1182 0.9795 0.6301 0.053 Uiso calc R 1 . .
C C11 0.1473(3) 0.7963(2) 0.7271(2) 0.0372(5) Uani d . 1 . .
C C12 0.1185(3) 0.8653(3) 0.8556(3) 0.0487(6) Uani d . 1 . .
H H12 0.0984 0.9694 0.8738 0.058 Uiso calc R 1 . .
C C13 0.1204(3) 0.7792(3) 0.9517(3) 0.0521(6) Uani d . 1 . .
H H13 0.1023 0.8237 1.0367 0.063 Uiso calc R 1 . .
C C14 0.1498(3) 0.6225(3) 0.9221(2) 0.0476(6) Uani d . 1 . .
H H14 0.1481 0.5646 0.9886 0.057 Uiso calc R 1 . .
C C15 0.1802(2) 0.6383(2) 0.7082(2) 0.0341(5) Uani d . 1 . .
C C16 0.2159(3) 0.5678(2) 0.5817(2) 0.0326(5) Uani d . 1 . .
C C17 0.4047(4) 0.2427(3) 0.8712(3) 0.0733(8) Uani d . 1 . .
H H17A 0.4457 0.2784 0.8026 0.110 Uiso calc R 1 . .
H H17B 0.4345 0.1394 0.8754 0.110 Uiso calc R 1 . .
H H17C 0.4594 0.3135 0.9641 0.110 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'
O O 0.0106 0.0060 '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'
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
C16 O1 C1 . . 118.65(15) ?
C17 O3 H3 . . 109.5 ?
C14 N1 C15 . . 117.14(18) ?
O1 C1 C2 . . 115.76(18) ?
O1 C1 C6 . . 122.41(18) ?
C2 C1 C6 . . 121.82(19) ?
C3 C2 C1 . . 119.0(2) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C2 C3 C4 . . 120.7(2) ?
C2 C3 H3a . . 119.6 ?
C4 C3 H3a . . 119.6 ?
C5 C4 C3 . . 119.9(2) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 121.0(2) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C1 C6 C5 . . 117.6(2) ?
C1 C6 C7 . . 120.34(19) ?
C5 C6 C7 . . 122.08(19) ?
O2 C7 C8 . . 122.5(2) ?
O2 C7 C6 . . 122.8(2) ?
C8 C7 C6 . . 114.67(18) ?
C16 C8 C9 . . 119.21(19) ?
C16 C8 C7 . . 120.17(18) ?
C9 C8 C7 . . 120.62(18) ?
C10 C9 C8 . . 121.3(2) ?
C10 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
C9 C10 C11 . . 120.6(2) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C15 C11 C12 . . 116.89(19) ?
C15 C11 C10 . . 119.7(2) ?
C12 C11 C10 . . 123.4(2) ?
C13 C12 C11 . . 119.7(2) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C12 C13 C14 . . 119.4(2) ?
C12 C13 H13 . . 120.3 ?
C14 C13 H13 . . 120.3 ?
N1 C14 C13 . . 123.9(2) ?
N1 C14 H14 . . 118.0 ?
C13 C14 H14 . . 118.0 ?
N1 C15 C11 . . 122.95(19) ?
N1 C15 C16 . . 119.13(18) ?
C11 C15 C16 . . 117.92(18) ?
O1 C16 C8 . . 123.74(18) ?
O1 C16 C15 . . 115.04(16) ?
C8 C16 C15 . . 121.22(18) ?
O3 C17 H17A . . 109.5 ?
O3 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O3 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 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 C16 . 1.363(2) ?
O1 C1 . 1.375(2) ?
O2 C7 . 1.227(2) ?
O3 C17 . 1.394(3) ?
O3 H3 . 0.8200 ?
N1 C14 . 1.321(3) ?
N1 C15 . 1.367(2) ?
C1 C2 . 1.384(3) ?
C1 C6 . 1.388(3) ?
C2 C3 . 1.371(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.386(3) ?
C3 H3a . 0.9300 ?
C4 C5 . 1.366(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.403(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.470(3) ?
C7 C8 . 1.466(3) ?
C8 C16 . 1.373(3) ?
C8 C9 . 1.417(3) ?
C9 C10 . 1.347(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.419(3) ?
C10 H10 . 0.9300 ?
C11 C15 . 1.415(3) ?
C11 C12 . 1.415(3) ?
C12 C13 . 1.352(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.399(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C16 . 1.429(3) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 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
O3 H3 N1 . 0.82 2.07 2.852(2) 160 y
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
C16 O1 C1 C2 . . . . -178.86(17) ?
C16 O1 C1 C6 . . . . 1.1(3) ?
O1 C1 C2 C3 . . . . 179.87(19) ?
C6 C1 C2 C3 . . . . -0.1(3) ?
C1 C2 C3 C4 . . . . 0.3(3) ?
C2 C3 C4 C5 . . . . -0.2(4) ?
C3 C4 C5 C6 . . . . -0.1(4) ?
O1 C1 C6 C5 . . . . 179.83(19) ?
C2 C1 C6 C5 . . . . -0.2(3) ?
O1 C1 C6 C7 . . . . -1.3(3) ?
C2 C1 C6 C7 . . . . 178.69(19) ?
C4 C5 C6 C1 . . . . 0.3(3) ?
C4 C5 C6 C7 . . . . -178.6(2) ?
C1 C6 C7 O2 . . . . 179.7(2) ?
C5 C6 C7 O2 . . . . -1.5(3) ?
C1 C6 C7 C8 . . . . 0.2(3) ?
C5 C6 C7 C8 . . . . 179.03(19) ?
O2 C7 C8 C16 . . . . -178.4(2) ?
C6 C7 C8 C16 . . . . 1.0(3) ?
O2 C7 C8 C9 . . . . 0.7(3) ?
C6 C7 C8 C9 . . . . -179.84(18) ?
C16 C8 C9 C10 . . . . 2.7(3) ?
C7 C8 C9 C10 . . . . -176.5(2) ?
C8 C9 C10 C11 . . . . -1.6(3) ?
C9 C10 C11 C15 . . . . -1.3(3) ?
C9 C10 C11 C12 . . . . 179.5(2) ?
C15 C11 C12 C13 . . . . -1.1(3) ?
C10 C11 C12 C13 . . . . 178.0(2) ?
C11 C12 C13 C14 . . . . -0.4(4) ?
C15 N1 C14 C13 . . . . -0.6(3) ?
C12 C13 C14 N1 . . . . 1.4(4) ?
C14 N1 C15 C11 . . . . -1.0(3) ?
C14 N1 C15 C16 . . . . 178.70(19) ?
C12 C11 C15 N1 . . . . 1.9(3) ?
C10 C11 C15 N1 . . . . -177.29(19) ?
C12 C11 C15 C16 . . . . -177.82(18) ?
C10 C11 C15 C16 . . . . 3.0(3) ?
C1 O1 C16 C8 . . . . 0.2(3) ?
C1 O1 C16 C15 . . . . -179.36(16) ?
C9 C8 C16 O1 . . . . 179.58(18) ?
C7 C8 C16 O1 . . . . -1.2(3) ?
C9 C8 C16 C15 . . . . -0.9(3) ?
C7 C8 C16 C15 . . . . 178.25(19) ?
N1 C15 C16 O1 . . . . -2.1(3) ?
C11 C15 C16 O1 . . . . 177.68(17) ?
N1 C15 C16 C8 . . . . 178.38(18) ?
C11 C15 C16 C8 . . . . -1.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655905
