#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/81/2208198.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_2208198
loop_
_publ_author_name
Zamarrud
'Viqar Uddin Ahmad'
'Shazia Anjum'
'M. Qaiser'
_publ_section_title
;
 5-Formyl-2,3-dihydroisocoumarin
;
_journal_coeditor_code           WN6408
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o405
_journal_page_last               o407
_journal_paper_doi               10.1107/S1600536805042558
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C10 H8 O3'
_chemical_formula_moiety         'C10 H8 O3'
_chemical_formula_sum            'C10 H8 O3'
_chemical_formula_weight         176.16
_chemical_melting_point          413.5(5)
_chemical_name_common            Erythrocentaurin
_chemical_name_systematic
;
5-Formyl-2,3-dihydroisocoumarin
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.337(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.651(3)
_cell_length_b                   4.0197(14)
_cell_length_c                   26.701(9)
_cell_measurement_reflns_used    2249
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.5
_cell_volume                     807.9(5)
_computing_cell_refinement       'SAINT  (Siemens,  1996)'
_computing_data_collection       'SMART  (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Siemens SMART CCD 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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            4155
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0686
_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)+(0.0527P)²+0.2194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1426
_reflns_number_gt                1151
_reflns_number_total             1573
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6408.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.

'_geom_hbond_publ_flag' value 'Y' changed to 'y' 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:

'_chemical_melting_point' value '413--414' was changed to '413.5(5)'
- the average value was taken and precision was estimated.

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 '413--414' was changed to '413.5(5)'
- the average value was taken and precision was
estimated.

'_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.

'_geom_hbond_publ_flag' value 'Y' changed to 'y'
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      'P 21/c'
_cod_database_code               2208198
_cod_database_fobs_code          2208198
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 0.0208(2) -0.9988(5) -0.09342(7) 0.0495(5) Uani d . 1 O
O2 -0.0825(3) -1.0212(6) -0.17496(8) 0.0675(7) Uani d . 1 O
O3 0.6988(3) -0.6428(6) -0.04433(8) 0.0678(7) Uani d . 1 O
C1 0.5010(3) -0.5840(6) -0.12432(9) 0.0358(6) Uani d . 1 C
C2 0.5005(4) -0.4717(7) -0.17383(10) 0.0461(7) Uani d . 1 C
H2A 0.6027 -0.3748 -0.1816 0.055 Uiso calc R 1 H
C3 0.3524(4) -0.5012(7) -0.21131(10) 0.0488(7) Uani d . 1 C
H3A 0.3543 -0.4238 -0.2440 0.059 Uiso calc R 1 H
C4 0.2021(4) -0.6458(7) -0.19996(9) 0.0449(7) Uani d . 1 C
H4A 0.1022 -0.6702 -0.2253 0.054 Uiso calc R 1 H
C5 0.0339(4) -0.9295(7) -0.14173(10) 0.0439(7) Uani d . 1 C
C6 0.1384(3) -0.8274(7) -0.05287(9) 0.0434(7) Uani d . 1 C
H6A 0.1281 -0.9273 -0.0205 0.052 Uiso calc R 1 H
H6B 0.1024 -0.5964 -0.0521 0.052 Uiso calc R 1 H
C7 0.3288(3) -0.8436(6) -0.05989(9) 0.0369(6) Uani d . 1 C
H7A 0.3713 -1.0709 -0.0553 0.044 Uiso calc R 1 H
H7B 0.4016 -0.7061 -0.0345 0.044 Uiso calc R 1 H
C8 0.3455(3) -0.7246(6) -0.11220(8) 0.0322(6) Uani d . 1 C
C9 0.1980(3) -0.7561(6) -0.15088(9) 0.0350(6) Uani d . 1 C
C10 0.6681(4) -0.5423(7) -0.08733(11) 0.0486(7) Uani d . 1 C
H10A 0.7589 -0.4260 -0.0985 0.058 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0381(11) 0.0610(13) 0.0498(11) -0.0156(10) 0.0088(9) 0.0005(9)
O2 0.0412(13) 0.0954(17) 0.0592(13) -0.0216(12) -0.0088(10) -0.0093(12)
O3 0.0389(12) 0.111(2) 0.0497(13) -0.0046(12) -0.0037(10) 0.0022(12)
C1 0.0303(14) 0.0374(14) 0.0404(14) 0.0008(11) 0.0079(11) -0.0031(11)
C2 0.0445(17) 0.0462(16) 0.0523(17) -0.0029(13) 0.0214(14) 0.0023(13)
C3 0.0569(19) 0.0558(17) 0.0350(14) 0.0027(15) 0.0121(13) 0.0080(13)
C4 0.0446(16) 0.0517(17) 0.0354(14) 0.0023(14) -0.0014(12) 0.0001(12)
C5 0.0357(16) 0.0480(16) 0.0467(16) -0.0030(13) 0.0042(13) -0.0021(13)
C6 0.0417(15) 0.0506(16) 0.0401(15) -0.0038(14) 0.0133(12) 0.0015(12)
C7 0.0348(14) 0.0398(14) 0.0351(13) -0.0012(12) 0.0037(11) 0.0027(11)
C8 0.0312(14) 0.0295(13) 0.0367(13) 0.0009(11) 0.0081(11) -0.0026(10)
C9 0.0310(14) 0.0355(14) 0.0372(14) 0.0019(11) 0.0031(11) -0.0022(10)
C10 0.0319(16) 0.0570(18) 0.0579(18) -0.0041(13) 0.0109(13) -0.0001(14)
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'
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
C5 O1 C6 118.4(2)
C2 C1 C8 119.3(2)
C2 C1 C10 116.8(2)
C8 C1 C10 123.9(2)
C3 C2 C1 121.5(3)
C3 C2 H2A 119.3
C1 C2 H2A 119.3
C4 C3 C2 119.4(2)
C4 C3 H3A 120.3
C2 C3 H3A 120.3
C3 C4 C9 120.4(2)
C3 C4 H4A 119.8
C9 C4 H4A 119.8
O2 C5 O1 118.4(2)
O2 C5 C9 123.9(3)
O1 C5 C9 117.7(2)
O1 C6 C7 111.8(2)
O1 C6 H6A 109.3
C7 C6 H6A 109.3
O1 C6 H6B 109.3
C7 C6 H6B 109.3
H6A C6 H6B 107.9
C6 C7 C8 110.4(2)
C6 C7 H7A 109.6
C8 C7 H7A 109.6
C6 C7 H7B 109.6
C8 C7 H7B 109.6
H7A C7 H7B 108.1
C9 C8 C1 118.2(2)
C9 C8 C7 117.9(2)
C1 C8 C7 123.9(2)
C4 C9 C8 121.2(2)
C4 C9 C5 117.7(2)
C8 C9 C5 121.0(2)
O3 C10 C1 126.7(3)
O3 C10 H10A 116.6
C1 C10 H10A 116.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.341(3)
O1 C6 1.452(3)
O2 C5 1.197(3)
O3 C10 1.200(3)
C1 C2 1.396(3)
C1 C8 1.406(3)
C1 C10 1.479(4)
C2 C3 1.376(4)
C2 H2A 0.9300
C3 C4 1.370(4)
C3 H3A 0.9300
C4 C9 1.389(3)
C4 H4A 0.9300
C5 C9 1.494(4)
C6 C7 1.503(3)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.503(3)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.392(3)
C10 H10A 0.9300
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
C7 H7B O3 1_555 0.97 2.3508 2.902(3) 115 y
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
C8 C1 C2 C3 -1.2(4)
C10 C1 C2 C3 179.4(2)
C1 C2 C3 C4 -0.4(4)
C2 C3 C4 C9 1.2(4)
C6 O1 C5 O2 -166.4(3)
C6 O1 C5 C9 16.4(3)
C5 O1 C6 C7 -49.6(3)
O1 C6 C7 C8 52.8(3)
C2 C1 C8 C9 2.1(4)
C10 C1 C8 C9 -178.7(2)
C2 C1 C8 C7 -178.0(2)
C10 C1 C8 C7 1.3(4)
C6 C7 C8 C9 -26.6(3)
C6 C7 C8 C1 153.4(2)
C3 C4 C9 C8 -0.3(4)
C3 C4 C9 C5 -176.4(2)
C1 C8 C9 C4 -1.3(4)
C7 C8 C9 C4 178.7(2)
C1 C8 C9 C5 174.7(2)
C7 C8 C9 C5 -5.3(3)
O2 C5 C9 C4 11.2(4)
O1 C5 C9 C4 -171.8(2)
O2 C5 C9 C8 -164.9(3)
O1 C5 C9 C8 12.0(4)
C2 C1 C10 O3 -174.4(3)
C8 C1 C10 O3 6.3(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 165975
