#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/68/2206817.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_2206817
loop_
_publ_author_name
'Guo, Cheng'
'Gu, Xi-Feng'
_publ_section_title
;
 Ethyl
 2-amino-4-(2-methoxyphenyl)-4H-benzo[h]chromene-3-carboxylate
;
_journal_coeditor_code           WW6412
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3104
_journal_page_last               o3105
_journal_paper_doi               10.1107/S1600536805025018
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C23 H21 N O4'
_chemical_formula_moiety         'C23 H21 N O4'
_chemical_formula_sum            'C23 H21 N O4'
_chemical_formula_weight         375.41
_chemical_name_systematic
;
Ethyl 2-amino-4-(2-methoxyphenyl)-4H-benzo[h]chromene-3-carboxylate
;
_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                101.45(3)
_cell_angle_beta                 96.33(3)
_cell_angle_gamma                96.82(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9960(14)
_cell_length_b                   10.542(2)
_cell_length_c                   13.522(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     961.3(4)
_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 (Siemens, 1996)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(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  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4100
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         1.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.219
_refine_ls_extinction_coef       0.050(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.09P)²+0.2P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1874
_reflns_number_gt                2310
_reflns_number_total             3775
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6412.cif
_cod_data_source_block           I
_cod_original_cell_volume        961.3(3)
_cod_database_code               2206817
_cod_database_fobs_code          2206817
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
O1 0.5852(2) 0.72409(16) 0.59936(13) 0.0624(5) Uani d . 1 O
O2 0.2646(3) 0.67207(19) 0.54931(15) 0.0746(6) Uani d . 1 O
O3 0.2670(2) 0.34957(15) 0.68622(13) 0.0562(5) Uani d . 1 O
O4 0.4026(3) 0.5735(2) 0.87238(14) 0.0756(6) Uani d . 1 O
N 0.0850(3) 0.4661(3) 0.60674(19) 0.0673(7) Uani d . 1 N
C1 0.7846(5) 0.9007(3) 0.5603(3) 0.0999(11) Uani d . 1 C
H1A 0.7868 0.9732 0.5272 0.150 Uiso calc R 1 H
H1B 0.8667 0.8412 0.5306 0.150 Uiso calc R 1 H
H1C 0.8308 0.9320 0.6316 0.150 Uiso calc R 1 H
C2 0.5813(4) 0.8317(3) 0.5474(2) 0.0730(8) Uani d . 1 C
H2A 0.4966 0.8911 0.5765 0.088 Uiso calc R 1 H
H2B 0.5332 0.7990 0.4756 0.088 Uiso calc R 1 H
C3 0.4136(4) 0.6500(2) 0.59612(17) 0.0543(6) Uani d . 1 C
C4 0.4286(3) 0.5459(2) 0.65041(17) 0.0486(5) Uani d . 1 C
C5 0.2668(3) 0.4590(2) 0.64685(17) 0.0508(6) Uani d . 1 C
C6 0.4448(3) 0.3168(2) 0.72188(17) 0.0513(6) Uani d . 1 C
C7 0.4318(4) 0.1904(2) 0.74412(17) 0.0549(6) Uani d . 1 C
C8 0.2574(4) 0.1034(3) 0.7279(2) 0.0685(7) Uani d . 1 C
H8A 0.1428 0.1275 0.7006 0.082 Uiso calc R 1 H
C9 0.2555(5) -0.0168(3) 0.7520(3) 0.0871(9) Uani d . 1 C
H9A 0.1398 -0.0744 0.7398 0.105 Uiso calc R 1 H
C10 0.4245(6) -0.0536(3) 0.7945(3) 0.0923(11) Uani d . 1 C
H10A 0.4204 -0.1345 0.8125 0.111 Uiso calc R 1 H
C11 0.5953(5) 0.0275(3) 0.8101(2) 0.0836(9) Uani d . 1 C
H11A 0.7075 0.0009 0.8379 0.100 Uiso calc R 1 H
C12 0.6065(4) 0.1519(3) 0.78486(19) 0.0637(7) Uani d . 1 C
C13 0.7822(4) 0.2386(3) 0.7979(2) 0.0699(8) Uani d . 1 C
H13A 0.8973 0.2141 0.8243 0.084 Uiso calc R 1 H
C14 0.7854(4) 0.3569(3) 0.77249(19) 0.0621(7) Uani d . 1 C
H14A 0.9033 0.4115 0.7809 0.075 Uiso calc R 1 H
C15 0.6138(3) 0.3993(2) 0.73355(17) 0.0506(6) Uani d . 1 C
C16 0.6195(3) 0.5339(2) 0.70939(16) 0.0503(6) Uani d . 1 C
H16A 0.7189 0.5418 0.6644 0.060 Uiso calc R 1 H
C17 0.6856(3) 0.6386(2) 0.80602(17) 0.0545(6) Uani d . 1 C
C18 0.8641(4) 0.7172(2) 0.8187(2) 0.0665(7) Uani d . 1 C
H18A 0.9395 0.7075 0.7659 0.080 Uiso calc R 1 H
C19 0.9331(5) 0.8090(3) 0.9067(3) 0.0835(9) Uani d . 1 C
H19A 1.0537 0.8599 0.9131 0.100 Uiso calc R 1 H
C20 0.8244(6) 0.8251(3) 0.9842(3) 0.0918(11) Uani d . 1 C
H20A 0.8713 0.8873 1.0437 0.110 Uiso calc R 1 H
C21 0.6441(6) 0.7499(3) 0.9759(2) 0.0811(9) Uani d . 1 C
H21A 0.5697 0.7624 1.0290 0.097 Uiso calc R 1 H
C22 0.5757(4) 0.6554(2) 0.88715(19) 0.0621(7) Uani d . 1 C
C23 0.2869(5) 0.5797(4) 0.9540(2) 0.0950(11) Uani d . 1 C
H23A 0.1709 0.5172 0.9326 0.143 Uiso calc R 1 H
H23B 0.2525 0.6660 0.9719 0.143 Uiso calc R 1 H
H23C 0.3598 0.5600 1.0121 0.143 Uiso calc R 1 H
H2 0.080(4) 0.538(3) 0.579(2) 0.083(9) Uiso d . 1 H
H1 0.005(4) 0.397(3) 0.594(2) 0.072(9) Uiso d . 1 H
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
C3 O1 C2 116.1(2) yes
C5 O3 C6 118.39(18) yes
C22 O4 C23 118.9(2) yes
C5 N H2 111.7(19) ?
C5 N H1 117(2) ?
H2 N H1 128(3) ?
C2 C1 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
O1 C2 C1 107.4(2) yes
O1 C2 H2A 110.2 ?
C1 C2 H2A 110.2 ?
O1 C2 H2B 110.2 ?
C1 C2 H2B 110.2 ?
H2A C2 H2B 108.5 ?
O2 C3 O1 120.9(2) yes
O2 C3 C4 126.2(2) yes
O1 C3 C4 112.9(2) yes
C5 C4 C3 118.3(2) yes
C5 C4 C16 120.9(2) ?
C3 C4 C16 120.8(2) yes
C4 C5 N 126.9(2) yes
C4 C5 O3 123.66(19) yes
N C5 O3 109.4(2) yes
C15 C6 O3 122.4(2) yes
C15 C6 C7 123.8(2) ?
O3 C6 C7 113.8(2) yes
C8 C7 C6 123.5(2) yes
C8 C7 C12 119.3(2) ?
C6 C7 C12 117.2(2) ?
C9 C8 C7 120.3(3) ?
C9 C8 H8A 119.8 ?
C7 C8 H8A 119.8 ?
C8 C9 C10 120.6(3) ?
C8 C9 H9A 119.7 ?
C10 C9 H9A 119.7 ?
C11 C10 C9 120.5(3) ?
C11 C10 H10A 119.8 ?
C9 C10 H10A 119.8 ?
C10 C11 C12 121.3(3) ?
C10 C11 H11A 119.4 ?
C12 C11 H11A 119.4 ?
C13 C12 C11 123.2(3) yes
C13 C12 C7 118.9(2) ?
C11 C12 C7 117.9(3) ?
C14 C13 C12 121.0(2) ?
C14 C13 H13A 119.5 ?
C12 C13 H13A 119.5 ?
C13 C14 C15 121.6(3) ?
C13 C14 H14A 119.2 ?
C15 C14 H14A 119.2 ?
C6 C15 C14 117.5(2) ?
C6 C15 C16 121.7(2) ?
C14 C15 C16 120.7(2) yes
C4 C16 C15 110.49(19) ?
C4 C16 C17 115.16(18) yes
C15 C16 C17 110.03(18) yes
C4 C16 H16A 106.9 ?
C15 C16 H16A 106.9 ?
C17 C16 H16A 106.9 ?
C18 C17 C22 117.5(2) ?
C18 C17 C16 120.4(2) yes
C22 C17 C16 122.1(2) yes
C19 C18 C17 122.2(3) ?
C19 C18 H18A 118.9 ?
C17 C18 H18A 118.9 ?
C20 C19 C18 119.7(3) ?
C20 C19 H19A 120.1 ?
C18 C19 H19A 120.1 ?
C19 C20 C21 120.8(3) ?
C19 C20 H20A 119.6 ?
C21 C20 H20A 119.6 ?
C20 C21 C22 119.3(3) ?
C20 C21 H21A 120.3 ?
C22 C21 H21A 120.3 ?
O4 C22 C21 124.0(3) yes
O4 C22 C17 115.6(2) yes
C21 C22 C17 120.4(3) ?
O4 C23 H23A 109.5 ?
O4 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
O4 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 1.344(3) yes
O1 C2 1.449(3) yes
O2 C3 1.230(3) yes
O3 C5 1.363(3) yes
O3 C6 1.391(3) yes
O4 C22 1.372(3) yes
O4 C23 1.435(3) yes
N C5 1.343(3) yes
N H2 0.91(3) ?
N H1 0.84(3) ?
C1 C2 1.494(4) yes
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C4 1.443(3) yes
C4 C5 1.360(3) ?
C4 C16 1.510(3) ?
C6 C15 1.356(3) ?
C6 C7 1.418(3) ?
C7 C8 1.405(4) ?
C7 C12 1.421(3) ?
C8 C9 1.368(4) ?
C8 H8A 0.9300 ?
C9 C10 1.388(5) ?
C9 H9A 0.9300 ?
C10 C11 1.354(5) ?
C10 H10A 0.9300 ?
C11 C12 1.414(4) ?
C11 H11A 0.9300 ?
C12 C13 1.414(4) ?
C13 C14 1.357(4) ?
C13 H13A 0.9300 ?
C14 C15 1.414(3) ?
C14 H14A 0.9300 ?
C15 C16 1.514(3) ?
C16 C17 1.521(3) yes
C16 H16A 0.9800 ?
C17 C18 1.387(4) ?
C17 C22 1.403(4) ?
C18 C19 1.376(4) ?
C18 H18A 0.9300 ?
C19 C20 1.356(5) ?
C19 H19A 0.9300 ?
C20 C21 1.389(5) ?
C20 H20A 0.9300 ?
C21 C22 1.396(4) ?
C21 H21A 0.9300 ?
C23 H23A 0.9600 ?
C23 H23B 0.9600 ?
C23 H23C 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
N H2 O2 . 0.91(3) 1.93(3) 2.671(4) 137(2) yes
C21 H21A Cg3 2_665 0.93 2.96 3.7227 141 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
C3 O1 C2 C1 179.9(2)
C2 O1 C3 O2 1.6(3)
C2 O1 C3 C4 -179.3(2)
O2 C3 C4 C5 3.3(4)
O1 C3 C4 C5 -175.7(2)
O2 C3 C4 C16 -176.9(2)
O1 C3 C4 C16 4.1(3)
C3 C4 C5 N -7.7(4)
C16 C4 C5 N 172.4(2)
C3 C4 C5 O3 173.2(2)
C16 C4 C5 O3 -6.7(3)
C6 O3 C5 C4 -7.4(3)
C6 O3 C5 N 173.3(2)
C5 O3 C6 C15 10.5(3)
C5 O3 C6 C7 -169.32(19)
C15 C6 C7 C8 -177.3(2)
O3 C6 C7 C8 2.5(3)
C15 C6 C7 C12 2.7(3)
O3 C6 C7 C12 -177.53(19)
C6 C7 C8 C9 -179.4(2)
C12 C7 C8 C9 0.6(4)
C7 C8 C9 C10 1.2(5)
C8 C9 C10 C11 -2.0(5)
C9 C10 C11 C12 0.8(5)
C10 C11 C12 C13 -178.7(3)
C10 C11 C12 C7 1.1(4)
C8 C7 C12 C13 178.0(2)
C6 C7 C12 C13 -1.9(3)
C8 C7 C12 C11 -1.8(3)
C6 C7 C12 C11 178.3(2)
C11 C12 C13 C14 180.0(2)
C7 C12 C13 C14 0.2(4)
C12 C13 C14 C15 1.0(4)
O3 C6 C15 C14 178.7(2)
C7 C6 C15 C14 -1.5(3)
O3 C6 C15 C16 0.7(3)
C7 C6 C15 C16 -179.5(2)
C13 C14 C15 C6 -0.3(3)
C13 C14 C15 C16 177.7(2)
C5 C4 C16 C15 16.0(3)
C3 C4 C16 C15 -163.9(2)
C5 C4 C16 C17 -109.5(2)
C3 C4 C16 C17 70.7(3)
C6 C15 C16 C4 -13.1(3)
C14 C15 C16 C4 169.0(2)
C6 C15 C16 C17 115.2(2)
C14 C15 C16 C17 -62.8(3)
C4 C16 C17 C18 -122.2(2)
C15 C16 C17 C18 112.1(2)
C4 C16 C17 C22 61.0(3)
C15 C16 C17 C22 -64.6(3)
C22 C17 C18 C19 -0.2(4)
C16 C17 C18 C19 -177.1(2)
C17 C18 C19 C20 -0.4(4)
C18 C19 C20 C21 0.1(5)
C19 C20 C21 C22 0.9(4)
C23 O4 C22 C21 -3.0(4)
C23 O4 C22 C17 176.6(2)
C20 C21 C22 O4 178.0(2)
C20 C21 C22 C17 -1.5(4)
C18 C17 C22 O4 -178.4(2)
C16 C17 C22 O4 -1.6(3)
C18 C17 C22 C21 1.2(3)
C16 C17 C22 C21 178.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2589660
