#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/15/2221569.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_2221569
loop_
_publ_author_name
'Jiao, Yuan-Hong'
'Zhang, Qian'
'Meng, Fa-Yan'
'Teng, Lei'
'Yuan, Jia'
'Ng, Seik Weng'
_publ_section_title
;
 Ethyl 3-amino-1-phenyl-1H-benzo[f]chromene-2-carboxylate
;
_journal_coeditor_code           ZL2186
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o775
_journal_paper_doi               10.1107/S1600536809008885
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H19 N O3'
_chemical_formula_moiety         'C22 H19 N O3'
_chemical_formula_sum            'C22 H19 N O3'
_chemical_formula_weight         345.38
_chemical_name_systematic
;
Ethyl 3-amino-1-phenyl-1H-benzo[f]chromene-2-carboxylate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.5510(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7835(5)
_cell_length_b                   14.6460(4)
_cell_length_c                   8.8713(2)
_cell_measurement_reflns_used    8058
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1766.05(9)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_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      153(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       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  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8563
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2029
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0296
_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)+(0.0522P)²+0.3553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0780
_reflns_number_gt                1958
_reflns_number_total             2029
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2186.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Multi-scan' changed
to 'multi-scan' 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 'Monoclinic' changed to 'monoclinic'
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 'Multi-scan'
changed to 'multi-scan' 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_original_sg_symbol_H-M      'C c'
_cod_database_code               2221569
_cod_database_fobs_code          2221569
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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 0.50000(10) 0.89966(8) 0.50000(13) 0.0251(3) Uani d . 1 . .
O O2 0.57192(9) 0.73346(8) 0.07916(12) 0.0221(3) Uani d . 1 . .
O O3 0.57203(10) 0.88667(8) 0.05998(13) 0.0243(3) Uani d . 1 . .
N N1 0.54563(13) 0.98073(10) 0.31277(17) 0.0289(3) Uani d D 1 . .
H H11 0.5480(18) 1.0271(12) 0.376(2) 0.038(7) Uiso d D 1 . .
H H12 0.5641(18) 0.9858(18) 0.2234(17) 0.040(7) Uiso d D 1 . .
C C1 0.53026(11) 0.72524(11) 0.36834(17) 0.0176(3) Uani d . 1 . .
H H1 0.4968 0.6810 0.2908 0.021 Uiso calc R 1 . .
C C2 0.63064(12) 0.68559(10) 0.43558(18) 0.0199(3) Uani d . 1 . .
C C3 0.66322(13) 0.60409(11) 0.3813(2) 0.0254(4) Uani d . 1 . .
H H3 0.6228 0.5728 0.3004 0.031 Uiso calc R 1 . .
C C4 0.75447(14) 0.56763(13) 0.4441(3) 0.0335(4) Uani d . 1 . .
H H4 0.7759 0.5118 0.4060 0.040 Uiso calc R 1 . .
C C5 0.81378(14) 0.61264(14) 0.5619(3) 0.0364(5) Uani d . 1 . .
H H5 0.8756 0.5874 0.6056 0.044 Uiso calc R 1 . .
C C6 0.78287(14) 0.69460(15) 0.6159(2) 0.0357(5) Uani d . 1 . .
H H6 0.8239 0.7260 0.6959 0.043 Uiso calc R 1 . .
C C7 0.69180(13) 0.73093(13) 0.5532(2) 0.0276(4) Uani d . 1 . .
H H7 0.6711 0.7871 0.5908 0.033 Uiso calc R 1 . .
C C8 0.46549(12) 0.73777(11) 0.48933(17) 0.0191(3) Uani d . 1 . .
C C9 0.41664(12) 0.66266(12) 0.54835(17) 0.0204(3) Uani d . 1 . .
C C10 0.43046(13) 0.57101(12) 0.50594(18) 0.0247(3) Uani d . 1 . .
H H10 0.4732 0.5580 0.4349 0.030 Uiso calc R 1 . .
C C11 0.38294(15) 0.50035(13) 0.5660(2) 0.0305(4) Uani d . 1 . .
H H11A 0.3941 0.4392 0.5378 0.037 Uiso calc R 1 . .
C C12 0.31800(14) 0.51858(14) 0.6691(2) 0.0322(4) Uani d . 1 . .
H H12A 0.2840 0.4698 0.7079 0.039 Uiso calc R 1 . .
C C13 0.30372(14) 0.60584(14) 0.7134(2) 0.0297(4) Uani d . 1 . .
H H13 0.2601 0.6172 0.7837 0.036 Uiso calc R 1 . .
C C14 0.35287(12) 0.68005(13) 0.65636(19) 0.0240(4) Uani d . 1 . .
C C15 0.34044(13) 0.77096(13) 0.7054(2) 0.0278(4) Uani d . 1 . .
H H15 0.2974 0.7827 0.7764 0.033 Uiso calc R 1 . .
C C16 0.38932(14) 0.84127(13) 0.65223(19) 0.0262(4) Uani d . 1 . .
H H16 0.3816 0.9018 0.6867 0.031 Uiso calc R 1 . .
C C17 0.45205(12) 0.82298(12) 0.54462(18) 0.0217(3) Uani d . 1 . .
C C18 0.53012(12) 0.89655(11) 0.36102(17) 0.0213(3) Uani d . 1 . .
C C19 0.53928(12) 0.81562(10) 0.28807(18) 0.0186(3) Uani d . 1 . .
C C20 0.56246(12) 0.81763(10) 0.13523(18) 0.0185(3) Uani d . 1 . .
C C21 0.59893(13) 0.72831(11) -0.07209(18) 0.0239(3) Uani d . 1 . .
H H21A 0.6644 0.7561 -0.0717 0.029 Uiso calc R 1 . .
H H21B 0.5502 0.7611 -0.1475 0.029 Uiso calc R 1 . .
C C22 0.60081(17) 0.62865(13) -0.1116(2) 0.0336(4) Uani d . 1 . .
H H22A 0.5345 0.6031 -0.1183 0.050 Uiso calc R 1 . .
H H22B 0.6459 0.5964 -0.0321 0.050 Uiso calc R 1 . .
H H22C 0.6232 0.6214 -0.2101 0.050 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C18 O1 C17 . . 117.34(13) ?
C20 O2 C21 . . 116.42(12) ?
C18 N1 H11 . . 120.2(17) ?
C18 N1 H12 . . 117.1(17) ?
H11 N1 H12 . . 122(2) ?
C8 C1 C19 . . 109.27(13) ?
C8 C1 C2 . . 111.78(13) ?
C19 C1 C2 . . 112.04(12) ?
C8 C1 H1 . . 107.9 ?
C19 C1 H1 . . 107.9 ?
C2 C1 H1 . . 107.9 ?
C3 C2 C7 . . 118.56(15) ?
C3 C2 C1 . . 121.00(14) ?
C7 C2 C1 . . 120.44(15) ?
C2 C3 C4 . . 120.82(17) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C5 C4 C3 . . 120.03(18) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 119.83(17) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C5 C6 C7 . . 120.10(18) ?
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C6 C7 C2 . . 120.65(18) ?
C6 C7 H7 . . 119.7 ?
C2 C7 H7 . . 119.7 ?
C17 C8 C9 . . 118.06(14) ?
C17 C8 C1 . . 119.73(14) ?
C9 C8 C1 . . 122.20(14) ?
C10 C9 C14 . . 118.23(15) ?
C10 C9 C8 . . 122.59(15) ?
C14 C9 C8 . . 119.17(15) ?
C11 C10 C9 . . 121.04(16) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C10 C11 C12 . . 120.21(18) ?
C10 C11 H11A . . 119.9 ?
C12 C11 H11A . . 119.9 ?
C13 C12 C11 . . 120.25(17) ?
C13 C12 H12A . . 119.9 ?
C11 C12 H12A . . 119.9 ?
C12 C13 C14 . . 121.08(17) ?
C12 C13 H13 . . 119.5 ?
C14 C13 H13 . . 119.5 ?
C13 C14 C15 . . 121.35(16) ?
C13 C14 C9 . . 119.15(16) ?
C15 C14 C9 . . 119.50(15) ?
C16 C15 C14 . . 120.85(16) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C15 C16 C17 . . 118.99(16) ?
C15 C16 H16 . . 120.5 ?
C17 C16 H16 . . 120.5 ?
C8 C17 O1 . . 122.40(14) ?
C8 C17 C16 . . 123.36(16) ?
O1 C17 C16 . . 114.24(14) ?
N1 C18 O1 . . 110.36(14) ?
N1 C18 C19 . . 128.13(15) ?
O1 C18 C19 . . 121.50(14) ?
C18 C19 C20 . . 118.64(14) ?
C18 C19 C1 . . 120.87(14) ?
C20 C19 C1 . . 120.42(13) ?
O3 C20 O2 . . 121.82(15) ?
O3 C20 C19 . . 125.89(14) ?
O2 C20 C19 . . 112.28(13) ?
O2 C21 C22 . . 106.43(13) ?
O2 C21 H21A . . 110.4 ?
C22 C21 H21A . . 110.4 ?
O2 C21 H21B . . 110.4 ?
C22 C21 H21B . . 110.4 ?
H21A C21 H21B . . 108.6 ?
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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C18 . 1.3654(19) ?
O1 C17 . 1.393(2) ?
O2 C20 . 1.3437(19) ?
O2 C21 . 1.4527(18) ?
O3 C20 . 1.231(2) ?
N1 C18 . 1.334(2) ?
N1 H11 . 0.876(10) ?
N1 H12 . 0.875(10) ?
C1 C8 . 1.517(2) ?
C1 C19 . 1.518(2) ?
C1 C2 . 1.528(2) ?
C1 H1 . 1.0000 ?
C2 C3 . 1.389(2) ?
C2 C7 . 1.396(2) ?
C3 C4 . 1.395(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.382(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.386(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.392(3) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C17 . 1.365(2) ?
C8 C9 . 1.433(2) ?
C9 C10 . 1.415(2) ?
C9 C14 . 1.427(2) ?
C10 C11 . 1.378(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.407(3) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.361(3) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.418(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.420(3) ?
C15 C16 . 1.357(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.416(2) ?
C16 H16 . 0.9500 ?
C18 C19 . 1.366(2) ?
C19 C20 . 1.444(2) ?
C21 C22 . 1.502(2) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
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
N1 H11 O3 2_575 0.880(10) 2.050(10) 2.907(2) 166(2) yes
N1 H12 O3 . 0.880(10) 2.07(2) 2.707(2) 129(2) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 C1 C2 C3 . . . . 121.86(16) ?
C19 C1 C2 C3 . . . . -115.10(16) ?
C8 C1 C2 C7 . . . . -58.27(19) ?
C19 C1 C2 C7 . . . . 64.76(19) ?
C7 C2 C3 C4 . . . . 0.8(2) ?
C1 C2 C3 C4 . . . . -179.31(16) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . -0.8(3) ?
C4 C5 C6 C7 . . . . 0.8(3) ?
C5 C6 C7 C2 . . . . 0.0(3) ?
C3 C2 C7 C6 . . . . -0.8(3) ?
C1 C2 C7 C6 . . . . 179.31(16) ?
C19 C1 C8 C17 . . . . -20.86(19) ?
C2 C1 C8 C17 . . . . 103.73(16) ?
C19 C1 C8 C9 . . . . 158.81(13) ?
C2 C1 C8 C9 . . . . -76.60(18) ?
C17 C8 C9 C10 . . . . -175.95(15) ?
C1 C8 C9 C10 . . . . 4.4(2) ?
C17 C8 C9 C14 . . . . 2.8(2) ?
C1 C8 C9 C14 . . . . -176.84(15) ?
C14 C9 C10 C11 . . . . 0.6(2) ?
C8 C9 C10 C11 . . . . 179.41(15) ?
C9 C10 C11 C12 . . . . 1.2(3) ?
C10 C11 C12 C13 . . . . -1.8(3) ?
C11 C12 C13 C14 . . . . 0.5(3) ?
C12 C13 C14 C15 . . . . -178.19(18) ?
C12 C13 C14 C9 . . . . 1.3(3) ?
C10 C9 C14 C13 . . . . -1.9(2) ?
C8 C9 C14 C13 . . . . 179.31(15) ?
C10 C9 C14 C15 . . . . 177.66(15) ?
C8 C9 C14 C15 . . . . -1.2(2) ?
C13 C14 C15 C16 . . . . 178.73(17) ?
C9 C14 C15 C16 . . . . -0.8(3) ?
C14 C15 C16 C17 . . . . 1.0(3) ?
C9 C8 C17 O1 . . . . 176.85(14) ?
C1 C8 C17 O1 . . . . -3.5(2) ?
C9 C8 C17 C16 . . . . -2.7(2) ?
C1 C8 C17 C16 . . . . 176.99(16) ?
C18 O1 C17 C8 . . . . 24.8(2) ?
C18 O1 C17 C16 . . . . -155.62(15) ?
C15 C16 C17 C8 . . . . 0.8(3) ?
C15 C16 C17 O1 . . . . -178.81(15) ?
C17 O1 C18 N1 . . . . 160.53(15) ?
C17 O1 C18 C19 . . . . -18.3(2) ?
N1 C18 C19 C20 . . . . -4.4(3) ?
O1 C18 C19 C20 . . . . 174.24(15) ?
N1 C18 C19 C1 . . . . 172.70(16) ?
O1 C18 C19 C1 . . . . -8.7(2) ?
C8 C1 C19 C18 . . . . 27.1(2) ?
C2 C1 C19 C18 . . . . -97.31(17) ?
C8 C1 C19 C20 . . . . -155.85(14) ?
C2 C1 C19 C20 . . . . 79.71(17) ?
C21 O2 C20 O3 . . . . 3.0(2) ?
C21 O2 C20 C19 . . . . -177.75(13) ?
C18 C19 C20 O3 . . . . -2.5(2) ?
C1 C19 C20 O3 . . . . -179.59(16) ?
C18 C19 C20 O2 . . . . 178.28(15) ?
C1 C19 C20 O2 . . . . 1.20(19) ?
C20 O2 C21 C22 . . . . -177.74(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2953653
