#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/40/4024087.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024087
loop_
_publ_author_name
'Ibrar Hussain'
'Van Thi Hong Nguyen'
'Mirza Arfan Yawer'
'Tuan Thanh Dang'
'Christine Fischer'
'Helmut Reinke'
'Peter Langer'
_publ_contact_author
;
      Peter Langer 
      Institut für Chemie
      Universität Rostock
      Albert-Einstein-Str. 3a
      D-18059 Rostock
      Germany
;
_publ_contact_author_email       peter.langer@uni-rostock.de
_publ_contact_author_fax         '049 381 498 6412'
_publ_contact_author_phone       '049 381 498 6410'
_publ_section_title
;
 Synthesis of Dibenzo[b,d]pyran-6-ones Based on [3 + 3] Cyclizations
 of 1,3-Bis(silyl enol ethers) with 3-Silyloxy-2-en-1-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6255
_journal_page_last               6258
_journal_paper_doi               10.1021/jo070608r
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C16 H14 O3'
_chemical_formula_weight         254.27
_chemical_melting_point          382
_chemical_name_systematic
; 
 8-Ethyl-7-hydroxy-9-methyl-6H-benzo[c]chromen-6-one 
;
_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                 98.0890(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3408(2)
_cell_length_b                   12.8642(2)
_cell_length_c                   7.74600(10)
_cell_measurement_reflns_used    6662
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      35.09
_cell_measurement_theta_min      3.33
_cell_volume                     1217.48(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16584
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       'part of prism'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0400
_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)+(0.0645P)²+0.2473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                2553
_reflns_number_total             3176
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070608rsi20070323_061057.cif
_cod_data_source_block           ah54
_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 
;
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024087
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.59187(7) 0.39947(6) 0.36376(11) 0.0361(2) Uani 1 1 d . . .
O2 O 0.74065(8) 0.46292(7) 0.28023(14) 0.0488(3) Uani 1 1 d . . .
O3 O 0.89192(8) 0.34288(8) 0.18826(12) 0.0434(2) Uani 1 1 d . . .
H3 H 0.8537(18) 0.4012(18) 0.213(3) 0.072(6) Uiso 1 1 d . . .
C1 C 0.68941(10) 0.38433(9) 0.30644(15) 0.0338(2) Uani 1 1 d . . .
C2 C 0.72603(9) 0.27896(8) 0.28201(13) 0.0281(2) Uani 1 1 d . . .
C3 C 0.66101(8) 0.19346(8) 0.31591(12) 0.0259(2) Uani 1 1 d . . .
C4 C 0.55489(8) 0.21431(8) 0.37163(12) 0.0263(2) Uani 1 1 d . . .
C5 C 0.52480(9) 0.31703(8) 0.39581(13) 0.0294(2) Uani 1 1 d . . .
C6 C 0.42689(10) 0.34429(9) 0.45241(15) 0.0360(3) Uani 1 1 d . . .
H6 H 0.4098 0.4152 0.4700 0.043 Uiso 1 1 calc R . .
C7 C 0.35496(10) 0.26671(10) 0.48254(15) 0.0377(3) Uani 1 1 d . . .
H7 H 0.2879 0.2839 0.5225 0.045 Uiso 1 1 calc R . .
C8 C 0.38015(10) 0.16332(10) 0.45468(15) 0.0360(3) Uani 1 1 d . . .
H8 H 0.3294 0.1102 0.4727 0.043 Uiso 1 1 calc R . .
C9 C 0.47891(9) 0.13755(9) 0.40070(14) 0.0317(2) Uani 1 1 d . . .
H9 H 0.4955 0.0666 0.3830 0.038 Uiso 1 1 calc R . .
C10 C 0.82846(9) 0.26226(9) 0.22459(14) 0.0315(2) Uani 1 1 d . . .
C11 C 0.86727(9) 0.16172(9) 0.20308(13) 0.0321(2) Uani 1 1 d . . .
C12 C 0.80304(9) 0.07744(9) 0.24091(14) 0.0316(2) Uani 1 1 d . . .
C13 C 0.70092(9) 0.09374(8) 0.29523(14) 0.0297(2) Uani 1 1 d . . .
H13 H 0.6579 0.0355 0.3185 0.036 Uiso 1 1 calc R . .
C14 C 0.84116(11) -0.03279(10) 0.22121(19) 0.0431(3) Uani 1 1 d . . .
H14A H 0.7924 -0.0807 0.2716 0.065 Uiso 1 1 calc R . .
H14B H 0.9159 -0.0406 0.2820 0.065 Uiso 1 1 calc R . .
H14C H 0.8399 -0.0487 0.0972 0.065 Uiso 1 1 calc R . .
C15 C 0.97699(10) 0.14782(11) 0.14092(16) 0.0425(3) Uani 1 1 d . . .
H15A H 0.9861 0.2026 0.0544 0.051 Uiso 1 1 calc R . .
H15B H 0.9780 0.0798 0.0814 0.051 Uiso 1 1 calc R . .
C16 C 1.07293(11) 0.15273(14) 0.2868(2) 0.0535(4) Uani 1 1 d . . .
H16A H 1.0761 0.2219 0.3403 0.080 Uiso 1 1 calc R . .
H16B H 1.1411 0.1393 0.2392 0.080 Uiso 1 1 calc R . .
H16C H 1.0635 0.1002 0.3750 0.080 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 121.88(8) . . ?
C10 O3 H3 104.6(13) . . ?
O2 C1 O1 116.05(10) . . ?
O2 C1 C2 124.94(11) . . ?
O1 C1 C2 119.01(10) . . ?
C3 C2 C10 119.88(10) . . ?
C3 C2 C1 120.66(10) . . ?
C10 C2 C1 119.46(10) . . ?
C13 C3 C2 118.59(9) . . ?
C13 C3 C4 123.38(9) . . ?
C2 C3 C4 118.04(9) . . ?
C5 C4 C9 116.73(10) . . ?
C5 C4 C3 118.78(9) . . ?
C9 C4 C3 124.48(9) . . ?
C6 C5 O1 115.52(9) . . ?
C6 C5 C4 122.90(10) . . ?
O1 C5 C4 121.58(10) . . ?
C7 C6 C5 118.76(10) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 120.25(11) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.15(11) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 121.17(10) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
O3 C10 C11 117.81(10) . . ?
O3 C10 C2 121.22(11) . . ?
C11 C10 C2 120.97(10) . . ?
C10 C11 C12 118.61(10) . . ?
C10 C11 C15 119.03(10) . . ?
C12 C11 C15 122.36(11) . . ?
C11 C12 C13 120.53(10) . . ?
C11 C12 C14 120.91(10) . . ?
C13 C12 C14 118.56(10) . . ?
C3 C13 C12 121.41(10) . . ?
C3 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 C16 113.46(10) . . ?
C11 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C11 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3545(15) . ?
O1 C5 1.3890(13) . ?
O2 C1 1.2244(14) . ?
O3 C10 1.3528(13) . ?
O3 H3 0.92(2) . ?
C1 C2 1.4497(15) . ?
C2 C3 1.4078(14) . ?
C2 C10 1.4142(16) . ?
C3 C13 1.3914(14) . ?
C3 C4 1.4602(15) . ?
C4 C5 1.3924(14) . ?
C4 C9 1.4016(15) . ?
C5 C6 1.3872(16) . ?
C6 C7 1.3773(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3896(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3832(16) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.3974(16) . ?
C11 C12 1.3982(16) . ?
C11 C15 1.5102(16) . ?
C12 C13 1.3994(15) . ?
C12 C14 1.5086(16) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.5184(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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
_geom_hbond_site_symmetry_A
O3 H3 O2 0.92(2) 1.75(2) 2.5984(15) 152(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 O2 178.94(9) . . . . ?
C5 O1 C1 C2 -1.56(15) . . . . ?
O2 C1 C2 C3 179.95(10) . . . . ?
O1 C1 C2 C3 0.49(15) . . . . ?
O2 C1 C2 C10 0.36(17) . . . . ?
O1 C1 C2 C10 -179.10(9) . . . . ?
C10 C2 C3 C13 1.36(14) . . . . ?
C1 C2 C3 C13 -178.24(9) . . . . ?
C10 C2 C3 C4 -178.81(9) . . . . ?
C1 C2 C3 C4 1.60(14) . . . . ?
C13 C3 C4 C5 177.15(9) . . . . ?
C2 C3 C4 C5 -2.68(14) . . . . ?
C13 C3 C4 C9 -3.86(16) . . . . ?
C2 C3 C4 C9 176.32(9) . . . . ?
C1 O1 C5 C6 -179.40(9) . . . . ?
C1 O1 C5 C4 0.43(15) . . . . ?
C9 C4 C5 C6 2.48(15) . . . . ?
C3 C4 C5 C6 -178.45(9) . . . . ?
C9 C4 C5 O1 -177.33(9) . . . . ?
C3 C4 C5 O1 1.74(14) . . . . ?
O1 C5 C6 C7 178.37(9) . . . . ?
C4 C5 C6 C7 -1.45(16) . . . . ?
C5 C6 C7 C8 -0.67(17) . . . . ?
C6 C7 C8 C9 1.63(18) . . . . ?
C7 C8 C9 C4 -0.54(17) . . . . ?
C5 C4 C9 C8 -1.45(15) . . . . ?
C3 C4 C9 C8 179.54(10) . . . . ?
C3 C2 C10 O3 178.91(9) . . . . ?
C1 C2 C10 O3 -1.49(15) . . . . ?
C3 C2 C10 C11 -0.91(15) . . . . ?
C1 C2 C10 C11 178.69(9) . . . . ?
O3 C10 C11 C12 179.66(9) . . . . ?
C2 C10 C11 C12 -0.51(15) . . . . ?
O3 C10 C11 C15 -0.02(15) . . . . ?
C2 C10 C11 C15 179.81(9) . . . . ?
C10 C11 C12 C13 1.47(16) . . . . ?
C15 C11 C12 C13 -178.86(10) . . . . ?
C10 C11 C12 C14 -179.59(10) . . . . ?
C15 C11 C12 C14 0.08(17) . . . . ?
C2 C3 C13 C12 -0.41(15) . . . . ?
C4 C3 C13 C12 179.77(9) . . . . ?
C11 C12 C13 C3 -1.03(16) . . . . ?
C14 C12 C13 C3 -179.99(10) . . . . ?
C10 C11 C15 C16 84.57(15) . . . . ?
C12 C11 C15 C16 -95.10(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658831
