#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/43/2204364.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_2204364
loop_
_publ_author_name
'Daqing Shi'
'Xiangshan Wang'
'Qiya Zhuang'
_publ_section_title
;
 Ethyl
 3-amino-1-(4-chlorophenyl)-1H-benzo[f]chromene-2-carboxylate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1807
_journal_page_last               o1809
_journal_paper_doi               10.1107/S1600536804022706
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C22 H18 Cl N O3'
_chemical_formula_moiety         'C22 H18 Cl N O3'
_chemical_formula_sum            'C22 H18 Cl N O3'
_chemical_formula_weight         379.82
_chemical_melting_point          464.0(10)
_chemical_name_systematic
;
Ethyl 3-amino-1-(4-chlorophenyl)-1H-benzo[f]chromene-2-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                94.990(10)
_cell_angle_beta                 98.14(2)
_cell_angle_gamma                102.840(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2920(10)
_cell_length_b                   9.4490(10)
_cell_length_c                   10.9730(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      12.72
_cell_measurement_theta_min      2.70
_cell_volume                     922.85(18)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'SHELXTL (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0103
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3558
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        3.62
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XSCANS; Siemens, 1994)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.243
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0393
_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)+(0.054P)²+0.0607P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                2323
_reflns_number_total             3229
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6271.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '463-465' was changed to '464.0(10)'
- the average value was taken and precision was
estimated.

'_exptl_absorpt_correction_type' tag value 'psi-scans'
was replaced with 'psi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '463-465' was changed to '464.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2204364
_cod_database_fobs_code          2204364
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
Cl 0.05933(9) 0.77428(8) 0.59584(7) 0.1088(3) Uani d . 1 Cl
O1 0.13354(14) 0.41314(15) -0.02708(11) 0.0577(4) Uani d . 1 O
O2 0.30937(15) 0.20823(13) 0.32189(12) 0.0573(4) Uani d . 1 O
O3 0.11007(15) 0.06971(14) 0.19128(13) 0.0663(4) Uani d . 1 O
N 0.00247(19) 0.1923(2) -0.0032(2) 0.0641(5) Uani d . 1 N
C1 0.1345(3) 0.6822(2) 0.4855(2) 0.0626(6) Uani d . 1 C
C2 0.0745(3) 0.6677(2) 0.3636(2) 0.0698(6) Uani d . 1 C
H2 -0.0076 0.7058 0.3391 0.084 Uiso calc R 1 H
C3 0.1351(2) 0.5969(2) 0.27645(18) 0.0579(5) Uani d . 1 C
H3 0.0935 0.5883 0.1931 0.069 Uiso calc R 1 H
C4 0.25562(18) 0.53849(17) 0.30962(15) 0.0390(4) Uani d . 1 C
C5 0.3122(2) 0.5532(3) 0.43321(18) 0.0718(6) Uani d . 1 C
H5 0.3931 0.5137 0.4587 0.086 Uiso calc R 1 H
C6 0.2521(3) 0.6254(3) 0.52190(19) 0.0824(7) Uani d . 1 C
H6 0.2927 0.6345 0.6055 0.099 Uiso calc R 1 H
C7 0.4844(2) 0.67177(18) 0.12810(17) 0.0473(4) Uani d . 1 C
C8 0.5904(2) 0.7065(2) 0.23884(19) 0.0556(5) Uani d . 1 C
H8 0.5785 0.6482 0.3025 0.067 Uiso calc R 1 H
C9 0.7099(2) 0.8244(2) 0.2538(2) 0.0698(6) Uani d . 1 C
H9 0.7788 0.8449 0.3269 0.084 Uiso calc R 1 H
C10 0.7292(3) 0.9143(3) 0.1601(3) 0.0815(8) Uani d . 1 C
H10 0.8094 0.9958 0.1719 0.098 Uiso calc R 1 H
C11 0.6316(3) 0.8833(2) 0.0523(3) 0.0756(7) Uani d . 1 C
H11 0.6470 0.9430 -0.0101 0.091 Uiso calc R 1 H
C12 0.5068(2) 0.7623(2) 0.03219(19) 0.0570(5) Uani d . 1 C
C13 0.4025(3) 0.7296(2) -0.0790(2) 0.0688(6) Uani d . 1 C
H13 0.4163 0.7888 -0.1418 0.083 Uiso calc R 1 H
C14 0.2828(3) 0.6140(2) -0.09642(19) 0.0636(6) Uani d . 1 C
H14 0.2156 0.5929 -0.1706 0.076 Uiso calc R 1 H
C15 0.2620(2) 0.52701(19) -0.00072(17) 0.0488(4) Uani d . 1 C
C16 0.35599(19) 0.55141(17) 0.11021(15) 0.0422(4) Uani d . 1 C
C17 0.31919(18) 0.45812(17) 0.21085(15) 0.0398(4) Uani d . 1 C
H17 0.4120 0.4368 0.2507 0.048 Uiso calc R 1 H
C18 0.21104(18) 0.31441(18) 0.15654(16) 0.0429(4) Uani d . 1 C
C19 0.11920(19) 0.30455(19) 0.04693(17) 0.0482(5) Uani d . 1 C
C20 0.2018(2) 0.18727(19) 0.22130(18) 0.0492(5) Uani d . 1 C
C21 0.3138(3) 0.0837(2) 0.3900(2) 0.0678(6) Uani d . 1 C
H21A 0.2125 0.0292 0.3909 0.081 Uiso calc R 1 H
H21B 0.3615 0.1182 0.4751 0.081 Uiso calc R 1 H
C22 0.3974(3) -0.0142(2) 0.3328(2) 0.0849(7) Uani d . 1 C
H22A 0.3468 -0.0532 0.2502 0.102 Uiso calc R 1 H
H22B 0.4026 -0.0929 0.3816 0.102 Uiso calc R 1 H
H22C 0.4969 0.0404 0.3295 0.102 Uiso calc R 1 H
H1B -0.021(2) 0.193(2) -0.081(2) 0.069(7) Uiso d . 1 H
H1A -0.003(3) 0.105(3) 0.044(3) 0.121(10) 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'
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
_geom_angle_publ_flag
C19 O1 C15 118.58(14) y
C20 O2 C21 116.71(15) y
C19 N H1B 111.5(15) ?
C19 N H1A 112.3(16) ?
H1B N H1A 128(2) ?
C6 C1 C2 120.28(19) ?
C6 C1 Cl 119.69(17) ?
C2 C1 Cl 120.03(18) ?
C1 C2 C3 120.1(2) ?
C1 C2 H2 120.0 ?
C3 C2 H2 120.0 ?
C4 C3 C2 121.45(18) ?
C4 C3 H3 119.3 ?
C2 C3 H3 119.3 ?
C5 C4 C3 117.09(17) ?
C5 C4 C17 122.54(16) ?
C3 C4 C17 120.35(15) ?
C4 C5 C6 121.8(2) ?
C4 C5 H5 119.1 ?
C6 C5 H5 119.1 ?
C1 C6 C5 119.3(2) ?
C1 C6 H6 120.3 ?
C5 C6 H6 120.3 ?
C8 C7 C12 118.02(17) ?
C8 C7 C16 122.64(17) ?
C12 C7 C16 119.33(17) ?
C9 C8 C7 121.0(2) ?
C9 C8 H8 119.5 ?
C7 C8 H8 119.5 ?
C8 C9 C10 120.5(2) ?
C8 C9 H9 119.7 ?
C10 C9 H9 119.7 ?
C11 C10 C9 120.1(2) ?
C11 C10 H10 119.9 ?
C9 C10 H10 119.9 ?
C10 C11 C12 121.4(2) ?
C10 C11 H11 119.3 ?
C12 C11 H11 119.3 ?
C13 C12 C11 122.2(2) ?
C13 C12 C7 118.92(18) ?
C11 C12 C7 118.8(2) ?
C14 C13 C12 121.52(19) ?
C14 C13 H13 119.2 ?
C12 C13 H13 119.2 ?
C13 C14 C15 118.7(2) ?
C13 C14 H14 120.6 ?
C15 C14 H14 120.6 ?
C16 C15 O1 122.16(16) y
C16 C15 C14 123.79(19) ?
O1 C15 C14 114.03(17) y
C15 C16 C7 117.71(16) ?
C15 C16 C17 120.03(15) y
C7 C16 C17 122.19(15) ?
C16 C17 C18 110.48(14) y
C16 C17 C4 111.09(13) y
C18 C17 C4 110.76(13) y
C16 C17 H17 108.1 ?
C18 C17 H17 108.1 ?
C4 C17 H17 108.1 ?
C19 C18 C20 119.02(16) y
C19 C18 C17 120.20(16) y
C20 C18 C17 120.77(16) y
N C19 C18 126.8(2) y
N C19 O1 110.69(18) y
C18 C19 O1 122.53(16) y
O3 C20 O2 121.29(17) y
O3 C20 C18 126.09(18) y
O2 C20 C18 112.62(15) y
O2 C21 C22 111.20(17) ?
O2 C21 H21A 109.4 ?
C22 C21 H21A 109.4 ?
O2 C21 H21B 109.4 ?
C22 C21 H21B 109.4 ?
H21A C21 H21B 108.0 ?
C21 C22 H22A 109.5 ?
C21 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
C21 C22 H22C 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C1 1.743(2) ?
O1 C19 1.358(2) y
O1 C15 1.394(2) y
O2 C20 1.349(2) y
O2 C21 1.452(2) y
O3 C20 1.227(2) y
N C19 1.350(2) y
N H1B 0.85(2) ?
N H1A 1.01(3) ?
C1 C6 1.348(3) ?
C1 C2 1.357(3) ?
C2 C3 1.374(3) ?
C2 H2 0.9300 ?
C3 C4 1.373(2) ?
C3 H3 0.9300 ?
C4 C5 1.367(2) ?
C4 C17 1.529(2) ?
C5 C6 1.390(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C8 1.415(3) ?
C7 C12 1.422(3) ?
C7 C16 1.431(2) ?
C8 C9 1.367(3) ?
C8 H8 0.9300 ?
C9 C10 1.396(3) ?
C9 H9 0.9300 ?
C10 C11 1.351(3) ?
C10 H10 0.9300 ?
C11 C12 1.413(3) ?
C11 H11 0.9300 ?
C12 C13 1.411(3) ?
C13 C14 1.353(3) ?
C13 H13 0.9300 ?
C14 C15 1.397(3) ?
C14 H14 0.9300 ?
C15 C16 1.363(2) y
C16 C17 1.502(2) y
C17 C18 1.514(2) y
C17 H17 0.9800 ?
C18 C19 1.356(2) ?
C18 C20 1.441(2) ?
C21 C22 1.486(3) ?
C21 H21A 0.9700 ?
C21 H21B 0.9700 ?
C22 H22A 0.9600 ?
C22 H22B 0.9600 ?
C22 H22C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N H1A O3 1.01(3) 1.89(3) 2.690(3) 133(2)
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
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.0(3) ?
Cl C1 C2 C3 179.09(16) ?
C1 C2 C3 C4 0.5(3) ?
C2 C3 C4 C5 0.4(3) ?
C2 C3 C4 C17 179.03(17) ?
C3 C4 C5 C6 -0.8(3) ?
C17 C4 C5 C6 -179.39(19) ?
C2 C1 C6 C5 0.6(4) ?
Cl C1 C6 C5 -179.47(18) ?
C4 C5 C6 C1 0.3(4) ?
C12 C7 C8 C9 0.7(3) ?
C16 C7 C8 C9 -178.44(16) ?
C7 C8 C9 C10 0.6(3) ?
C8 C9 C10 C11 -1.7(3) ?
C9 C10 C11 C12 1.4(3) ?
C10 C11 C12 C13 179.0(2) ?
C10 C11 C12 C7 -0.1(3) ?
C8 C7 C12 C13 179.97(17) ?
C16 C7 C12 C13 -0.9(2) ?
C8 C7 C12 C11 -0.9(2) ?
C16 C7 C12 C11 178.19(16) ?
C11 C12 C13 C14 -179.42(18) ?
C7 C12 C13 C14 -0.4(3) ?
C12 C13 C14 C15 0.9(3) ?
C19 O1 C15 C16 -15.3(2) y
C19 O1 C15 C14 166.09(15) y
C13 C14 C15 C16 -0.1(3) ?
C13 C14 C15 O1 178.53(16) ?
O1 C15 C16 C7 -179.65(14) ?
C14 C15 C16 C7 -1.1(3) ?
O1 C15 C16 C17 -2.6(2) ?
C14 C15 C16 C17 175.90(16) ?
C8 C7 C16 C15 -179.31(16) ?
C12 C7 C16 C15 1.6(2) ?
C8 C7 C16 C17 3.7(2) ?
C12 C7 C16 C17 -175.37(14) ?
C15 C16 C17 C18 21.3(2) ?
C7 C16 C17 C18 -161.83(14) ?
C15 C16 C17 C4 -102.07(17) ?
C7 C16 C17 C4 74.83(19) ?
C5 C4 C17 C16 -127.64(19) ?
C3 C4 C17 C16 53.8(2) ?
C5 C4 C17 C18 109.2(2) ?
C3 C4 C17 C18 -69.4(2) ?
C16 C17 C18 C19 -24.9(2) ?
C4 C17 C18 C19 98.60(18) y
C16 C17 C18 C20 156.35(14) ?
C4 C17 C18 C20 -80.12(19) y
C20 C18 C19 N 9.8(3) ?
C17 C18 C19 N -168.97(16) ?
C20 C18 C19 O1 -171.58(15) y
C17 C18 C19 O1 9.7(3) y
C15 O1 C19 N -169.63(14) y
C15 O1 C19 C18 11.5(2) y
C21 O2 C20 O3 1.9(2) ?
C21 O2 C20 C18 -177.08(15) ?
C19 C18 C20 O3 -5.3(3) ?
C17 C18 C20 O3 173.39(16) ?
C19 C18 C20 O2 173.60(15) ?
C17 C18 C20 O2 -7.7(2) ?
C20 O2 C21 C22 83.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2116512
