#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/32/2213227.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_2213227
loop_
_publ_author_name
'D. Gayathri'
'D. Velmurugan'
'K. Ravikumar'
'K. Geetha'
'H. Surya Prakash Rao'
_publ_section_title
;
 2-[2-(Methylamino)-3-nitro-4H-chromen-4-yl]phenyl acetate
;
_journal_coeditor_code           CI2343
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2300
_journal_page_last               o2302
_journal_paper_doi               10.1107/S1600536807015681
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C18 H16 N2 O5'
_chemical_formula_moiety         'C18 H16 N2 O5'
_chemical_formula_sum            'C18 H16 N2 O5'
_chemical_formula_weight         340.33
_chemical_name_systematic
;
2-[2-(Methylamino)-3-nitro-4H-chromen-4-yl]phenyl acetate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 96.4400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.7412(13)
_cell_length_b                   8.3846(5)
_cell_length_c                   16.1457(9)
_cell_measurement_reflns_used    1849
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.98
_cell_measurement_theta_min      2.58
_cell_volume                     3193.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'Bruker SMART APEX area-detector'
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17564
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         2.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0430
_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)+(0.0683P)²+1.1833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1254
_reflns_number_gt                3193
_reflns_number_total             3756
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2343.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.

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2213227
_cod_database_fobs_code          2213227
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'
'-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
C C1 0.42696(5) 0.12224(14) -0.08563(8) 0.0416(3) Uani d . 1
C C2 0.45343(6) 0.18373(16) -0.15090(9) 0.0507(3) Uani d . 1
H H2 0.4394 0.1630 -0.2060 0.061 Uiso calc R 1
C C3 0.50108(6) 0.27631(17) -0.13213(10) 0.0570(4) Uani d . 1
H H3 0.5193 0.3200 -0.1749 0.068 Uiso calc R 1
C C4 0.52182(6) 0.30436(18) -0.05049(11) 0.0594(4) Uani d . 1
H H4 0.5542 0.3661 -0.0382 0.071 Uiso calc R 1
C C5 0.49463(5) 0.24095(17) 0.01329(9) 0.0516(3) Uani d . 1
H H5 0.5091 0.2604 0.0683 0.062 Uiso calc R 1
C C6 0.44589(5) 0.14839(14) -0.00332(8) 0.0404(3) Uani d . 1
C C7 0.41439(5) 0.08465(14) 0.06624(7) 0.0393(3) Uani d . 1
H H7 0.4409 0.0183 0.1022 0.047 Uiso calc R 1
C C8 0.36606(5) -0.02023(13) 0.03169(7) 0.0387(3) Uani d . 1
C C9 0.34973(5) -0.03870(13) -0.05361(7) 0.0387(3) Uani d . 1
C C10 0.29442(7) -0.1457(2) -0.17822(9) 0.0601(4) Uani d . 1
H H10A 0.2933 -0.0443 -0.2060 0.090 Uiso calc R 1
H H10B 0.2583 -0.1974 -0.1897 0.090 Uiso calc R 1
H H10C 0.3233 -0.2110 -0.1980 0.090 Uiso calc R 1
C C11 0.39731(5) 0.22432(14) 0.11856(7) 0.0400(3) Uani d . 1
C C12 0.42461(6) 0.24920(19) 0.19836(8) 0.0538(3) Uani d . 1
H H12 0.4500 0.1731 0.2220 0.065 Uiso calc R 1
C C13 0.41465(7) 0.3850(2) 0.24330(9) 0.0654(4) Uani d . 1
H H13 0.4337 0.4002 0.2962 0.078 Uiso calc R 1
C C14 0.37687(7) 0.4964(2) 0.20985(10) 0.0636(4) Uani d . 1
H H14 0.3707 0.5885 0.2396 0.076 Uiso calc R 1
C C15 0.34780(6) 0.47297(17) 0.13213(10) 0.0546(3) Uani d . 1
H H15 0.3213 0.5476 0.1098 0.066 Uiso calc R 1
C C16 0.35833(5) 0.33763(15) 0.08762(8) 0.0418(3) Uani d . 1
C C17 0.32820(6) 0.41031(17) -0.05361(9) 0.0515(3) Uani d . 1
C C18 0.28639(7) 0.3624(2) -0.12467(10) 0.0675(4) Uani d . 1
H H18A 0.2808 0.4489 -0.1636 0.101 Uiso calc R 1
H H18B 0.2510 0.3362 -0.1044 0.101 Uiso calc R 1
H H18C 0.3004 0.2710 -0.1518 0.101 Uiso calc R 1
N N1 0.30695(4) -0.12197(13) -0.08906(6) 0.0456(3) Uani d . 1
H H1 0.2847 -0.1657 -0.0572 0.055 Uiso calc R 1
N N2 0.33750(4) -0.09860(12) 0.08866(6) 0.0447(3) Uani d . 1
O O1 0.37860(4) 0.03261(12) -0.11002(5) 0.0490(2) Uani d . 1
O O2 0.29324(4) -0.17915(12) 0.06513(6) 0.0565(3) Uani d . 1
O O3 0.35495(5) -0.08877(13) 0.16421(6) 0.0610(3) Uani d . 1
O O4 0.32637(4) 0.30655(10) 0.01109(6) 0.0484(2) Uani d . 1
O O5 0.35963(6) 0.52058(15) -0.05145(8) 0.0789(4) Uani d . 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'
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
C6 C1 C2 123.37(11) ?
C6 C1 O1 122.05(10) ?
C2 C1 O1 114.58(11) ?
C3 C2 C1 118.28(14) ?
C3 C2 H2 120.9 ?
C1 C2 H2 120.9 ?
C4 C3 C2 120.29(13) ?
C4 C3 H3 119.9 ?
C2 C3 H3 119.9 ?
C3 C4 C5 120.12(13) ?
C3 C4 H4 119.9 ?
C5 C4 H4 119.9 ?
C4 C5 C6 121.19(14) ?
C4 C5 H5 119.4 ?
C6 C5 H5 119.4 ?
C1 C6 C5 116.75(12) ?
C1 C6 C7 121.77(10) ?
C5 C6 C7 121.46(11) ?
C8 C7 C6 110.56(10) ?
C8 C7 C11 114.55(10) ?
C6 C7 C11 108.89(9) ?
C8 C7 H7 107.5 ?
C6 C7 H7 107.5 ?
C11 C7 H7 107.5 ?
N2 C8 C9 120.34(10) ?
N2 C8 C7 116.50(10) ?
C9 C8 C7 123.16(10) ?
N1 C9 O1 111.79(10) ?
N1 C9 C8 127.28(11) ?
O1 C9 C8 120.92(10) ?
N1 C10 H10A 109.5 ?
N1 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
N1 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
C16 C11 C12 117.11(12) ?
C16 C11 C7 122.50(10) ?
C12 C11 C7 120.18(11) ?
C13 C12 C11 121.28(14) ?
C13 C12 H12 119.4 ?
C11 C12 H12 119.4 ?
C14 C13 C12 119.94(14) ?
C14 C13 H13 120.0 ?
C12 C13 H13 120.0 ?
C13 C14 C15 120.22(14) ?
C13 C14 H14 119.9 ?
C15 C14 H14 119.9 ?
C14 C15 C16 119.36(14) ?
C14 C15 H15 120.3 ?
C16 C15 H15 120.3 ?
C11 C16 C15 122.04(12) ?
C11 C16 O4 117.79(11) ?
C15 C16 O4 120.03(12) ?
O5 C17 O4 123.28(13) ?
O5 C17 C18 126.65(14) ?
O4 C17 C18 110.06(13) ?
C17 C18 H18A 109.5 ?
C17 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C17 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C9 N1 C10 124.70(10) y
C9 N1 H1 117.7 ?
C10 N1 H1 117.7 ?
O3 N2 O2 120.04(10) ?
O3 N2 C8 119.36(10) ?
O2 N2 C8 120.60(10) ?
C9 O1 C1 121.10(10) y
C17 O4 C16 119.80(10) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.3719(18) ?
C1 C2 1.3855(17) ?
C1 O1 1.3920(10) y
C2 C3 1.377(2) ?
C2 H2 0.93 ?
C3 C4 1.375(2) ?
C3 H3 0.93 ?
C4 C5 1.382(2) ?
C4 H4 0.93 ?
C5 C6 1.3941(17) ?
C5 H5 0.93 ?
C6 C7 1.5149(17) ?
C7 C8 1.5025(15) ?
C7 C11 1.5252(17) ?
C7 H7 0.98 ?
C8 N2 1.3702(15) ?
C8 C9 1.3968(17) ?
C9 N1 1.310(2) y
C9 O1 1.3410(10) y
C10 N1 1.451(2) y
C10 H10A 0.96 ?
C10 H10B 0.96 ?
C10 H10C 0.96 ?
C11 C16 1.3802(17) ?
C11 C12 1.3916(17) ?
C12 C13 1.385(2) ?
C12 H12 0.93 ?
C13 C14 1.364(3) ?
C13 H13 0.93 ?
C14 C15 1.377(2) ?
C14 H14 0.93 ?
C15 C16 1.3809(19) ?
C15 H15 0.93 ?
C16 O4 1.4000(15) ?
C17 O5 1.1862(18) ?
C17 O4 1.3638(16) ?
C17 C18 1.486(2) ?
C18 H18A 0.96 ?
C18 H18B 0.96 ?
C18 H18C 0.96 ?
N1 H1 0.86 ?
N2 O3 1.2460(10) y
N2 O2 1.2710(10) y
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 H1 O2 . 0.86 1.97 2.5910(10) 129
N1 H1 O2 7_545 0.86 2.25 2.9660(10) 140
C4 H4 O5 5_665 0.93 2.55 3.427(2) 157
C15 H15 O2 1_565 0.93 2.47 3.323(2) 152
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 -0.2(2) ?
O1 C1 C2 C3 178.88(12) ?
C1 C2 C3 C4 0.8(2) ?
C2 C3 C4 C5 -0.6(2) ?
C3 C4 C5 C6 -0.2(2) ?
C2 C1 C6 C5 -0.56(19) ?
O1 C1 C6 C5 -179.60(11) ?
C2 C1 C6 C7 177.46(12) ?
O1 C1 C6 C7 -1.59(18) ?
C4 C5 C6 C1 0.78(19) ?
C4 C5 C6 C7 -177.24(12) ?
C1 C6 C7 C8 6.03(15) ?
C5 C6 C7 C8 -176.05(11) ?
C1 C6 C7 C11 -120.66(12) ?
C5 C6 C7 C11 57.26(14) ?
C6 C7 C8 N2 173.67(10) ?
C11 C7 C8 N2 -62.85(13) ?
C6 C7 C8 C9 -6.77(16) ?
C11 C7 C8 C9 116.71(12) ?
N2 C8 C9 N1 2.55(19) ?
C7 C8 C9 N1 -176.99(11) ?
N2 C8 C9 O1 -177.52(11) ?
C7 C8 C9 O1 2.93(18) ?
C8 C7 C11 C16 -57.88(15) ?
C6 C7 C11 C16 66.49(14) ?
C8 C7 C11 C12 127.59(12) ?
C6 C7 C11 C12 -108.05(13) ?
C16 C11 C12 C13 -2.5(2) ?
C7 C11 C12 C13 172.34(13) ?
C11 C12 C13 C14 0.9(2) ?
C12 C13 C14 C15 1.2(2) ?
C13 C14 C15 C16 -1.6(2) ?
C12 C11 C16 C15 2.07(18) ?
C7 C11 C16 C15 -172.63(11) ?
C12 C11 C16 O4 -173.68(11) ?
C7 C11 C16 O4 11.62(17) ?
C14 C15 C16 C11 -0.1(2) ?
C14 C15 C16 O4 175.58(12) ?
O1 C9 N1 C10 4.6(2) y
C8 C9 N1 C10 -175.50(10) y
C9 C8 N2 O3 175.40(10) y
C7 C8 N2 O3 -5.02(16) ?
C9 C8 N2 O2 -5.4(2) y
C7 C8 N2 O2 174.14(10) ?
N1 C9 O1 C1 -177.59(10) ?
C8 C9 O1 C1 2.47(17) ?
C6 C1 O1 C9 -3.15(18) ?
C2 C1 O1 C9 177.73(11) ?
O5 C17 O4 C16 7.0(2) y
C18 C17 O4 C16 -173.80(10) y
C11 C16 O4 C17 -122.00(10) y
C15 C16 O4 C17 62.1(2) y
