#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/05/2220535.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_2220535
loop_
_publ_author_name
'Zhang, Jinpeng'
'Zhang, Xiaohong'
'Yan, Shu'
'Ma, Ning'
'Tu, Shujiang'
_publ_section_title
2-Amino-4-(2-chlorophenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile
_journal_coeditor_code           HK2585
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5
_journal_paper_doi               10.1107/S1600536808039986
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H11 Cl N2 O3'
_chemical_formula_moiety         'C20 H11 Cl N2 O3'
_chemical_formula_sum            'C20 H11 Cl N2 O3'
_chemical_formula_weight         362.76
_chemical_melting_point_gt       573
_chemical_name_systematic
;
2-Amino-4-(2-chlorophenyl)-5,10-dioxo-5,10-dihydro-4H-
benzo[g]chromene-3-carbonitrile
;
_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                93.0150(10)
_cell_angle_beta                 96.3930(10)
_cell_angle_gamma                110.732(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3201(10)
_cell_length_b                   9.3729(12)
_cell_length_c                   11.0081(16)
_cell_measurement_reflns_used    959
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.109
_cell_measurement_theta_min      2.822
_cell_volume                     793.95(18)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0799
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4207
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_correction_T_min  0.9564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0530
_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)+(0.0295P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.1004
_reflns_number_gt                1566
_reflns_number_total             2746
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2585.cif
_cod_data_source_block           I
_cod_database_code               2220535
_cod_database_fobs_code          2220535
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
Cl Cl1 -0.01619(12) 0.04001(10) 0.69113(9) 0.0587(3) Uani d . 1 . .
O O1 0.1440(3) 0.3890(2) 0.6133(2) 0.0405(6) Uani d . 1 . .
O O2 0.5886(3) 0.2063(3) 0.7464(2) 0.0541(7) Uani d . 1 . .
O O3 0.2251(3) 0.3753(3) 0.3898(2) 0.0536(7) Uani d . 1 . .
N N1 -0.0034(3) 0.4822(3) 0.7313(2) 0.0471(8) Uani d . 1 . .
H H1A -0.0304 0.5099 0.7994 0.057 Uiso calc R 1 . .
H H1B -0.0556 0.4936 0.6626 0.057 Uiso calc R 1 . .
N N2 0.1921(4) 0.4871(4) 1.0491(3) 0.0578(9) Uani d . 1 . .
C C1 0.1196(4) 0.4216(3) 0.7320(3) 0.0369(8) Uani d . 1 . .
C C2 0.2135(4) 0.3957(3) 0.8299(3) 0.0344(8) Uani d . 1 . .
C C3 0.3297(4) 0.3028(3) 0.8197(3) 0.0336(8) Uani d . 1 . .
H H3 0.4412 0.3622 0.8696 0.040 Uiso calc R 1 . .
C C4 0.3646(4) 0.2940(3) 0.6883(3) 0.0309(8) Uani d . 1 . .
C C5 0.5061(4) 0.2424(3) 0.6626(3) 0.0360(8) Uani d . 1 . .
C C6 0.5448(4) 0.2361(3) 0.5342(3) 0.0339(8) Uani d . 1 . .
C C7 0.6774(4) 0.1889(4) 0.5076(3) 0.0466(9) Uani d . 1 . .
H H7 0.7416 0.1604 0.5699 0.056 Uiso calc R 1 . .
C C8 0.7152(5) 0.1837(4) 0.3890(3) 0.0538(10) Uani d . 1 . .
H H8 0.8064 0.1540 0.3718 0.065 Uiso calc R 1 . .
C C9 0.6180(4) 0.2225(4) 0.2961(3) 0.0530(10) Uani d . 1 . .
H H9 0.6426 0.2170 0.2160 0.064 Uiso calc R 1 . .
C C10 0.4851(4) 0.2690(4) 0.3207(3) 0.0461(9) Uani d . 1 . .
H H10 0.4202 0.2951 0.2574 0.055 Uiso calc R 1 . .
C C11 0.4476(4) 0.2770(3) 0.4401(3) 0.0346(8) Uani d . 1 . .
C C12 0.3083(4) 0.3326(3) 0.4679(3) 0.0350(8) Uani d . 1 . .
C C13 0.2762(4) 0.3374(3) 0.5983(3) 0.0337(8) Uani d . 1 . .
C C14 0.1989(4) 0.4470(4) 0.9505(3) 0.0405(9) Uani d . 1 . .
C C15 0.2617(4) 0.1487(3) 0.8721(3) 0.0322(8) Uani d . 1 . .
C C16 0.1126(4) 0.0269(4) 0.8235(3) 0.0374(9) Uani d . 1 . .
C C17 0.0573(4) -0.1101(4) 0.8767(3) 0.0450(9) Uani d . 1 . .
H H17 -0.0427 -0.1903 0.8412 0.054 Uiso calc R 1 . .
C C18 0.1515(5) -0.1260(4) 0.9819(3) 0.0538(10) Uani d . 1 . .
H H18 0.1157 -0.2177 1.0179 0.065 Uiso calc R 1 . .
C C19 0.2985(5) -0.0068(4) 1.0343(3) 0.0514(10) Uani d . 1 . .
H H19 0.3613 -0.0172 1.1065 0.062 Uiso calc R 1 . .
C C20 0.3530(4) 0.1287(4) 0.9798(3) 0.0433(9) Uani d . 1 . .
H H20 0.4532 0.2084 1.0158 0.052 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'
Cl Cl 0.1484 0.1585 '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
C13 O1 C1 . . 117.4(2) ?
C1 N1 H1A . . 120.0 ?
C1 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
N1 C1 C2 . . 127.8(3) ?
N1 C1 O1 . . 110.1(3) ?
C2 C1 O1 . . 122.1(3) ?
C1 C2 C14 . . 120.4(3) ?
C1 C2 C3 . . 122.9(3) ?
C14 C2 C3 . . 116.6(3) ?
C4 C3 C2 . . 108.4(2) ?
C4 C3 C15 . . 114.8(2) ?
C2 C3 C15 . . 113.2(3) ?
C4 C3 H3 . . 106.6 ?
C2 C3 H3 . . 106.6 ?
C15 C3 H3 . . 106.6 ?
C13 C4 C5 . . 120.3(3) ?
C13 C4 C3 . . 121.8(3) ?
C5 C4 C3 . . 117.8(3) ?
O2 C5 C4 . . 119.6(3) ?
O2 C5 C6 . . 121.8(3) ?
C4 C5 C6 . . 118.6(3) ?
C7 C6 C11 . . 119.7(3) ?
C7 C6 C5 . . 119.8(3) ?
C11 C6 C5 . . 120.6(3) ?
C8 C7 C6 . . 120.2(3) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C9 C8 C7 . . 120.0(4) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C10 C9 C8 . . 120.5(4) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C11 . . 120.0(3) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C10 C11 C6 . . 119.6(3) ?
C10 C11 C12 . . 120.2(3) ?
C6 C11 C12 . . 120.2(3) ?
O3 C12 C11 . . 122.6(3) ?
O3 C12 C13 . . 120.7(3) ?
C11 C12 C13 . . 116.8(3) ?
C4 C13 O1 . . 124.6(3) ?
C4 C13 C12 . . 123.5(3) ?
O1 C13 C12 . . 111.9(3) ?
N2 C14 C2 . . 177.6(4) ?
C16 C15 C20 . . 116.6(3) ?
C16 C15 C3 . . 125.4(3) ?
C20 C15 C3 . . 118.0(3) ?
C15 C16 C17 . . 122.3(3) ?
C15 C16 Cl1 . . 120.9(2) ?
C17 C16 Cl1 . . 116.8(3) ?
C18 C17 C16 . . 119.4(3) ?
C18 C17 H17 . . 120.3 ?
C16 C17 H17 . . 120.3 ?
C17 C18 C19 . . 120.1(3) ?
C17 C18 H18 . . 120.0 ?
C19 C18 H18 . . 120.0 ?
C18 C19 C20 . . 119.9(3) ?
C18 C19 H19 . . 120.0 ?
C20 C19 H19 . . 120.0 ?
C19 C20 C15 . . 121.6(3) ?
C19 C20 H20 . . 119.2 ?
C15 C20 H20 . . 119.2 ?
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
Cl1 C16 . 1.747(3) ?
O1 C1 . 1.380(4) ?
O1 C13 . 1.370(3) ?
O2 C5 . 1.223(3) ?
O3 C12 . 1.216(3) ?
N1 C1 . 1.334(3) ?
N1 H1A . 0.8600 ?
N1 H1B . 0.8600 ?
N2 C14 . 1.144(4) ?
C1 C2 . 1.343(4) ?
C2 C14 . 1.420(5) ?
C2 C3 . 1.522(4) ?
C3 C4 . 1.510(4) ?
C3 C15 . 1.524(4) ?
C3 H3 . 0.9800 ?
C4 C13 . 1.335(4) ?
C4 C5 . 1.470(4) ?
C5 C6 . 1.487(4) ?
C6 C7 . 1.380(4) ?
C6 C11 . 1.396(4) ?
C7 C8 . 1.379(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.377(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.372(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.389(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.482(4) ?
C12 C13 . 1.490(4) ?
C15 C16 . 1.383(4) ?
C15 C20 . 1.393(4) ?
C16 C17 . 1.387(4) ?
C17 C18 . 1.370(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.373(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.383(4) ?
C19 H19 . 0.9300 ?
C20 H20 . 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
N1 H1A N2 2_567 0.86 2.26 3.080(4) 159.2
N1 H1B O3 2_566 0.86 2.22 2.889(3) 133.9
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
C13 O1 C1 N1 . . . . 174.8(2) ?
C13 O1 C1 C2 . . . . -3.9(4) ?
N1 C1 C2 C14 . . . . -5.9(6) ?
O1 C1 C2 C14 . . . . 172.6(3) ?
N1 C1 C2 C3 . . . . 169.9(3) ?
O1 C1 C2 C3 . . . . -11.5(5) ?
C1 C2 C3 C4 . . . . 18.2(4) ?
C14 C2 C3 C4 . . . . -165.8(3) ?
C1 C2 C3 C15 . . . . -110.3(4) ?
C14 C2 C3 C15 . . . . 65.6(4) ?
C2 C3 C4 C13 . . . . -11.5(4) ?
C15 C3 C4 C13 . . . . 116.1(3) ?
C2 C3 C4 C5 . . . . 165.6(3) ?
C15 C3 C4 C5 . . . . -66.7(3) ?
C13 C4 C5 O2 . . . . 178.4(3) ?
C3 C4 C5 O2 . . . . 1.1(4) ?
C13 C4 C5 C6 . . . . -1.6(4) ?
C3 C4 C5 C6 . . . . -178.8(3) ?
O2 C5 C6 C7 . . . . -0.2(5) ?
C4 C5 C6 C7 . . . . 179.7(3) ?
O2 C5 C6 C11 . . . . 179.5(3) ?
C4 C5 C6 C11 . . . . -0.6(4) ?
C11 C6 C7 C8 . . . . 0.7(5) ?
C5 C6 C7 C8 . . . . -179.5(3) ?
C6 C7 C8 C9 . . . . -1.4(5) ?
C7 C8 C9 C10 . . . . 1.1(5) ?
C8 C9 C10 C11 . . . . -0.1(5) ?
C9 C10 C11 C6 . . . . -0.6(5) ?
C9 C10 C11 C12 . . . . 177.8(3) ?
C7 C6 C11 C10 . . . . 0.3(5) ?
C5 C6 C11 C10 . . . . -179.5(3) ?
C7 C6 C11 C12 . . . . -178.1(3) ?
C5 C6 C11 C12 . . . . 2.1(4) ?
C10 C11 C12 O3 . . . . -1.4(5) ?
C6 C11 C12 O3 . . . . 177.0(3) ?
C10 C11 C12 C13 . . . . 179.9(3) ?
C6 C11 C12 C13 . . . . -1.7(4) ?
C5 C4 C13 O1 . . . . -179.1(3) ?
C3 C4 C13 O1 . . . . -2.0(5) ?
C5 C4 C13 C12 . . . . 2.0(5) ?
C3 C4 C13 C12 . . . . 179.1(3) ?
C1 O1 C13 C4 . . . . 11.0(4) ?
C1 O1 C13 C12 . . . . -170.1(3) ?
O3 C12 C13 C4 . . . . -179.1(3) ?
C11 C12 C13 C4 . . . . -0.4(4) ?
O3 C12 C13 O1 . . . . 1.9(4) ?
C11 C12 C13 O1 . . . . -179.4(2) ?
C4 C3 C15 C16 . . . . -57.8(4) ?
C2 C3 C15 C16 . . . . 67.4(4) ?
C4 C3 C15 C20 . . . . 124.2(3) ?
C2 C3 C15 C20 . . . . -110.6(3) ?
C20 C15 C16 C17 . . . . -1.4(5) ?
C3 C15 C16 C17 . . . . -179.4(3) ?
C20 C15 C16 Cl1 . . . . 178.3(2) ?
C3 C15 C16 Cl1 . . . . 0.2(4) ?
C15 C16 C17 C18 . . . . 0.8(5) ?
Cl1 C16 C17 C18 . . . . -178.8(3) ?
C16 C17 C18 C19 . . . . 0.4(5) ?
C17 C18 C19 C20 . . . . -1.0(5) ?
C18 C19 C20 C15 . . . . 0.4(5) ?
C16 C15 C20 C19 . . . . 0.8(5) ?
C3 C15 C20 C19 . . . . 179.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13068549
