#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/68/2206816.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_2206816
loop_
_publ_author_name
'Guo, Cheng'
'Gu, Xi-feng'
_publ_section_title
;
 Ethyl
 2-amino-4-(4-methoxyphenyl)-4H-benzo[h]chromene-3-carboxylate
;
_journal_coeditor_code           WW6411
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3101
_journal_page_last               o3103
_journal_paper_doi               10.1107/S1600536805025006
_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-(4-methoxyphenyl)-4H-benzo[h]chromene-3-carboxylate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 102.99(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.060(2)
_cell_length_b                   18.511(4)
_cell_length_c                   8.9360(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1943.8(7)
_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 (Siemens, 1996)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4053
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.219
_refine_ls_extinction_coef       0.0084(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0554
_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          0.1480
_refine_ls_wR_factor_ref         0.1838
_reflns_number_gt                2000
_reflns_number_total             3800
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6411.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206816
_cod_database_fobs_code          2206816
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_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 0.6715(2) -0.22638(11) 0.7492(3) 0.0846(7) Uani d . 1 O
O2 0.69231(15) 0.16586(10) 0.5640(2) 0.0550(5) Uani d . 1 O
O3 0.52120(18) 0.16532(11) 0.9261(2) 0.0643(6) Uani d . 1 O
O4 0.63883(17) 0.07651(10) 1.0369(2) 0.0629(6) Uani d . 1 O
N 0.5476(2) 0.21060(14) 0.6477(3) 0.0596(7) Uani d . 1 N
C1 0.7365(3) -0.27841(18) 0.8473(6) 0.1104(15) Uani d . 1 C
H1A 0.7102 -0.3260 0.8138 0.166 Uiso calc R 1 H
H1B 0.7281 -0.2709 0.9505 0.166 Uiso calc R 1 H
H1C 0.8152 -0.2737 0.8440 0.166 Uiso calc R 1 H
C2 0.6967(2) -0.15443(15) 0.7802(4) 0.0586(8) Uani d . 1 C
C3 0.6506(2) -0.10659(15) 0.6632(3) 0.0583(7) Uani d . 1 C
H3A 0.6049 -0.1237 0.5721 0.070 Uiso calc R 1 H
C4 0.6724(2) -0.03385(14) 0.6817(3) 0.0517(7) Uani d . 1 C
H4A 0.6409 -0.0023 0.6026 0.062 Uiso calc R 1 H
C5 0.7404(2) -0.00653(14) 0.8161(3) 0.0449(6) Uani d . 1 C
C6 0.7843(2) -0.05501(16) 0.9315(3) 0.0596(8) Uani d . 1 C
H6A 0.8296 -0.0380 1.0229 0.072 Uiso calc R 1 H
C7 0.7626(3) -0.12805(17) 0.9147(4) 0.0638(8) Uani d . 1 C
H7A 0.7928 -0.1595 0.9946 0.077 Uiso calc R 1 H
C8 0.7699(2) 0.07347(14) 0.8303(3) 0.0481(6) Uani d . 1 C
H8A 0.8170 0.0817 0.9334 0.058 Uiso calc R 1 H
C9 0.8411(2) 0.09238(14) 0.7147(3) 0.0511(7) Uani d . 1 C
C10 0.9512(2) 0.06370(17) 0.7314(4) 0.0697(9) Uani d . 1 C
H10A 0.9822 0.0363 0.8180 0.084 Uiso calc R 1 H
C11 1.0134(3) 0.07506(19) 0.6241(4) 0.0792(10) Uani d . 1 C
H11A 1.0864 0.0559 0.6390 0.095 Uiso calc R 1 H
C12 0.9681(3) 0.11582(16) 0.4894(4) 0.0648(8) Uani d . 1 C
C13 1.0271(3) 0.12540(19) 0.3697(5) 0.0833(11) Uani d . 1 C
H13A 1.0997 0.1062 0.3801 0.100 Uiso calc R 1 H
C14 0.9781(3) 0.16244(18) 0.2399(5) 0.0876(11) Uani d . 1 C
H14A 1.0179 0.1680 0.1627 0.105 Uiso calc R 1 H
C15 0.8698(3) 0.19210(18) 0.2205(4) 0.0783(10) Uani d . 1 C
H15A 0.8374 0.2169 0.1308 0.094 Uiso calc R 1 H
C16 0.8109(3) 0.18462(16) 0.3348(4) 0.0652(8) Uani d . 1 C
H16A 0.7393 0.2055 0.3229 0.078 Uiso calc R 1 H
C17 0.8580(2) 0.14559(13) 0.4700(3) 0.0523(7) Uani d . 1 C
C18 0.7989(2) 0.13317(13) 0.5892(3) 0.0485(7) Uani d . 1 C
C19 0.6359(2) 0.16548(13) 0.6811(3) 0.0464(6) Uani d . 1 C
C20 0.6688(2) 0.12318(13) 0.8090(3) 0.0482(6) Uani d . 1 C
C21 0.6020(2) 0.12564(14) 0.9249(3) 0.0512(7) Uani d . 1 C
C22 0.5728(3) 0.06875(18) 1.1529(3) 0.0697(9) Uani d . 1 C
H22A 0.4936 0.0593 1.1052 0.084 Uiso calc R 1 H
H22B 0.5771 0.1125 1.2136 0.084 Uiso calc R 1 H
C23 0.6229(3) 0.0064(2) 1.2524(3) 0.0866(11) Uani d . 1 C
H23A 0.5815 -0.0006 1.3313 0.130 Uiso calc R 1 H
H23B 0.7012 0.0164 1.2986 0.130 Uiso calc R 1 H
H23C 0.6181 -0.0365 1.1909 0.130 Uiso calc R 1 H
H2 0.498(3) 0.2154(15) 0.710(4) 0.073(9) Uiso d . 1 H
H1 0.541(3) 0.2434(18) 0.576(4) 0.084(11) 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
C2 O1 C1 117.8(3) yes
C19 O2 C18 118.3(2) yes
C21 O4 C22 117.0(2) yes
C19 N H2 121.7(19) ?
C19 N H1 123(2) ?
H2 N H1 115(3) ?
O1 C1 H1A 109.5 ?
O1 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
O1 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C7 C2 O1 125.2(3) yes
C7 C2 C3 119.2(3) ?
O1 C2 C3 115.6(3) yes
C4 C3 C2 120.1(3) ?
C4 C3 H3A 120.0 ?
C2 C3 H3A 120.0 ?
C3 C4 C5 121.4(3) ?
C3 C4 H4A 119.3 ?
C5 C4 H4A 119.3 ?
C6 C5 C4 117.5(3) ?
C6 C5 C8 121.9(2) yes
C4 C5 C8 120.5(2) yes
C7 C6 C5 121.6(3) ?
C7 C6 H6A 119.2 ?
C5 C6 H6A 119.2 ?
C2 C7 C6 120.2(3) ?
C2 C7 H7A 119.9 ?
C6 C7 H7A 119.9 ?
C20 C8 C5 114.7(2) yes
C20 C8 C9 109.7(2) ?
C5 C8 C9 108.9(2) yes
C20 C8 H8A 107.8 ?
C5 C8 H8A 107.8 ?
C9 C8 H8A 107.8 ?
C18 C9 C10 117.9(3) ?
C18 C9 C8 121.7(2) ?
C10 C9 C8 120.2(3) yes
C11 C10 C9 121.6(3) ?
C11 C10 H10A 119.2 ?
C9 C10 H10A 119.2 ?
C10 C11 C12 120.8(3) ?
C10 C11 H11A 119.6 ?
C12 C11 H11A 119.6 ?
C17 C12 C11 118.8(3) ?
C17 C12 C13 118.3(3) ?
C11 C12 C13 122.8(3) yes
C14 C13 C12 120.6(3) ?
C14 C13 H13A 119.7 ?
C12 C13 H13A 119.7 ?
C13 C14 C15 121.3(3) ?
C13 C14 H14A 119.4 ?
C15 C14 H14A 119.4 ?
C16 C15 C14 119.7(3) ?
C16 C15 H15A 120.2 ?
C14 C15 H15A 120.2 ?
C15 C16 C17 120.7(3) ?
C15 C16 H16A 119.6 ?
C17 C16 H16A 119.6 ?
C16 C17 C12 119.4(3) ?
C16 C17 C18 123.3(2) ?
C12 C17 C18 117.3(3) ?
C9 C18 O2 122.5(2) yes
C9 C18 C17 123.5(2) ?
O2 C18 C17 114.0(2) yes
N C19 C20 127.8(2) yes
N C19 O2 109.6(2) yes
C20 C19 O2 122.6(2) yes
C19 C20 C21 118.4(2) yes
C19 C20 C8 122.0(2) ?
C21 C20 C8 119.6(2) yes
O3 C21 O4 121.9(3) yes
O3 C21 C20 126.7(3) yes
O4 C21 C20 111.4(2) yes
O4 C22 C23 106.7(3) yes
O4 C22 H22A 110.4 ?
C23 C22 H22A 110.4 ?
O4 C22 H22B 110.4 ?
C23 C22 H22B 110.4 ?
H22A C22 H22B 108.6 ?
C22 C23 H23A 109.5 ?
C22 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
C22 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 C2 1.380(3) yes
O1 C1 1.415(4) yes
O2 C19 1.370(3) yes
O2 C18 1.393(3) yes
O3 C21 1.222(3) yes
O4 C21 1.351(3) yes
O4 C22 1.449(3) yes
N C19 1.333(3) yes
N H2 0.91(3) ?
N H1 0.87(3) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 C7 1.373(4) ?
C2 C3 1.387(4) ?
C3 C4 1.375(4) ?
C3 H3A 0.9300 ?
C4 C5 1.388(3) ?
C4 H4A 0.9300 ?
C5 C6 1.379(3) ?
C5 C8 1.522(4) yes
C6 C7 1.379(4) ?
C6 H6A 0.9300 ?
C7 H7A 0.9300 ?
C8 C20 1.504(4) ?
C8 C9 1.525(4) ?
C8 H8A 0.9800 ?
C9 C18 1.353(4) ?
C9 C10 1.407(4) ?
C10 C11 1.360(4) ?
C10 H10A 0.9300 ?
C11 C12 1.422(4) ?
C11 H11A 0.9300 ?
C12 C17 1.412(4) ?
C12 C13 1.422(4) ?
C13 C14 1.362(5) ?
C13 H13A 0.9300 ?
C14 C15 1.391(5) ?
C14 H14A 0.9300 ?
C15 C16 1.376(4) ?
C15 H15A 0.9300 ?
C16 C17 1.413(4) ?
C16 H16A 0.9300 ?
C17 C18 1.427(4) ?
C19 C20 1.369(4) ?
C20 C21 1.450(4) yes
C22 C23 1.498(4) yes
C22 H22A 0.9700 ?
C22 H22B 0.9700 ?
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 H1 O3 4_565 0.87(3) 2.14(3) 3.002(3) 172(3) yes
N H2 O3 . 0.91(4) 2.10(3) 2.711(3) 123(3) yes
N H2 O1 2_656 0.91(4) 2.41(4) 3.207(4) 147(3) yes
C4 H4A Cg1 . 0.93 2.68 3.0280(10) 142 yes
C22 H22A Cg2 3_657 0.97 2.90 3.636(4) 134 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
C1 O1 C2 C7 -14.3(4)
C1 O1 C2 C3 165.5(3)
C7 C2 C3 C4 0.9(4)
O1 C2 C3 C4 -178.8(2)
C2 C3 C4 C5 0.1(4)
C3 C4 C5 C6 -0.8(4)
C3 C4 C5 C8 175.9(2)
C4 C5 C6 C7 0.5(4)
C8 C5 C6 C7 -176.2(3)
O1 C2 C7 C6 178.5(3)
C3 C2 C7 C6 -1.2(4)
C5 C6 C7 C2 0.5(4)
C6 C5 C8 C20 -124.4(3)
C4 C5 C8 C20 59.1(3)
C6 C5 C8 C9 112.3(3)
C4 C5 C8 C9 -64.3(3)
C20 C8 C9 C18 -16.9(3)
C5 C8 C9 C18 109.4(3)
C20 C8 C9 C10 167.1(2)
C5 C8 C9 C10 -66.6(3)
C18 C9 C10 C11 -1.2(5)
C8 C9 C10 C11 174.9(3)
C9 C10 C11 C12 -0.9(5)
C10 C11 C12 C17 1.2(5)
C10 C11 C12 C13 -176.1(3)
C17 C12 C13 C14 0.0(5)
C11 C12 C13 C14 177.3(3)
C12 C13 C14 C15 0.2(6)
C13 C14 C15 C16 0.6(6)
C14 C15 C16 C17 -1.6(5)
C15 C16 C17 C12 1.8(4)
C15 C16 C17 C18 -177.0(3)
C11 C12 C17 C16 -178.4(3)
C13 C12 C17 C16 -1.0(4)
C11 C12 C17 C18 0.5(4)
C13 C12 C17 C18 177.9(3)
C10 C9 C18 O2 -178.0(2)
C8 C9 C18 O2 5.9(4)
C10 C9 C18 C17 3.1(4)
C8 C9 C18 C17 -173.0(2)
C19 O2 C18 C9 9.9(4)
C19 O2 C18 C17 -171.2(2)
C16 C17 C18 C9 176.1(3)
C12 C17 C18 C9 -2.8(4)
C16 C17 C18 O2 -2.8(4)
C12 C17 C18 O2 178.3(2)
C18 O2 C19 N 167.9(2)
C18 O2 C19 C20 -12.8(4)
N C19 C20 C21 0.4(4)
O2 C19 C20 C21 -178.8(2)
N C19 C20 C8 178.9(3)
O2 C19 C20 C8 -0.2(4)
C5 C8 C20 C19 -108.7(3)
C9 C8 C20 C19 14.2(3)
C5 C8 C20 C21 69.8(3)
C9 C8 C20 C21 -167.3(2)
C22 O4 C21 O3 4.7(4)
C22 O4 C21 C20 -174.6(2)
C19 C20 C21 O3 -4.7(4)
C8 C20 C21 O3 176.7(3)
C19 C20 C21 O4 174.5(2)
C8 C20 C21 O4 -4.0(3)
C21 O4 C22 C23 174.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2138526
