#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/19/2201901.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_2201901
loop_
_publ_author_name
'R. Krishna'
'S. Selvanayagam'
'M. Yogavel'
'D. Velmurugan'
'S. Manikandan'
_publ_section_title
'[6a,16b]-cis-7,7-Dimethyl-6,6a,7,16b-tetrahydrochromeno[4',3':3,4]pyrano[3,2-c]-α-naphthocoumarin'
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o667
_journal_page_last               o669
_journal_paper_doi               10.1107/S160053680300789X
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C25 H20 O4'
_chemical_formula_moiety         'C25 H20 O4'
_chemical_formula_sum            'C25 H20 O4'
_chemical_formula_weight         384.41
_chemical_name_systematic
;
[6a,16b]-cis-7,7-Dimethyl-6,6a,7,16b-
tetrahydrochromeno[4',3':3,4]pyrano[3,2-c]-α-naphthocoumarin
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.580(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1720(10)
_cell_length_b                   9.1400(10)
_cell_length_c                   18.0810(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35
_cell_measurement_theta_min      15
_cell_volume                     1927.9(3)
_computing_cell_refinement       'CAD4 EXPRESS'
_computing_data_collection       'CAD4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia,1997) and PLATON (Spek, 1990)
;
_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 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3967
_diffrn_reflns_theta_full        71.91
_diffrn_reflns_theta_max         71.91
_diffrn_reflns_theta_min         3.92
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.254
_refine_ls_extinction_coef       0.0045(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0491
_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)+(0.0905P)²+0.3018P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1531
_reflns_number_gt                2686
_reflns_number_total             3783
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6219.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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2201901
_cod_database_fobs_code          2201901
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.68391(10) 0.79519(16) 0.10818(7) 0.0528(4) Uani d . 1 . . O
C2 0.68450(16) 0.7257(2) 0.17611(10) 0.0508(5) Uani d . 1 . . C
C3 0.58192(15) 0.6570(2) 0.18167(9) 0.0440(4) Uani d . 1 . . C
C4 0.48988(14) 0.6497(2) 0.11790(9) 0.0417(4) Uani d . 1 . . C
C5 0.49193(14) 0.7184(2) 0.04648(9) 0.0430(4) Uani d . 1 . . C
C6 0.39750(16) 0.7161(2) -0.02126(10) 0.0516(5) Uani d . 1 . . C
H6 0.3305 0.6674 -0.0211 0.062 Uiso calc R 1 . . H
C7 0.40477(16) 0.7847(2) -0.08620(10) 0.0531(5) Uani d . 1 . . C
H7 0.3425 0.7820 -0.1302 0.064 Uiso calc R 1 . . H
C8 0.50480(15) 0.8601(2) -0.08835(9) 0.0452(4) Uani d . 1 . . C
C9 0.51411(18) 0.9306(2) -0.15618(11) 0.0527(5) Uani d . 1 . . C
H9 0.4522 0.9295 -0.2004 0.063 Uiso calc R 1 . . H
C10 0.6122(2) 0.9996(2) -0.15725(12) 0.0583(5) Uani d . 1 . . C
H10 0.6172 1.0435 -0.2026 0.070 Uiso calc R 1 . . H
C11 0.70632(19) 1.0058(2) -0.09097(12) 0.0597(5) Uani d . 1 . . C
H11 0.7725 1.0552 -0.0923 0.072 Uiso calc R 1 . . H
C12 0.70080(17) 0.9394(2) -0.02445(11) 0.0530(5) Uani d . 1 . . C
H12 0.7635 0.9433 0.0193 0.064 Uiso calc R 1 . . H
C13 0.60074(15) 0.8649(2) -0.02168(9) 0.0436(4) Uani d . 1 . . C
C14 0.58970(15) 0.7905(2) 0.04481(9) 0.0430(4) Uani d . 1 . . C
O15 0.39235(10) 0.57902(16) 0.11412(7) 0.0517(4) Uani d . 1 . . O
C16 0.37477(15) 0.5139(2) 0.18455(11) 0.0456(4) Uani d . 1 . . C
C17 0.49121(16) 0.4570(2) 0.23484(11) 0.0470(4) Uani d . 1 . . C
H17 0.5171 0.3844 0.2036 0.056 Uiso calc R 1 . . H
C18 0.4903(2) 0.3799(2) 0.30928(13) 0.0616(6) Uani d . 1 . . C
H18A 0.4292 0.3079 0.2975 0.074 Uiso calc R 1 . . H
H18B 0.5622 0.3277 0.3289 0.074 Uiso calc R 1 . . H
O19 0.47520(15) 0.4735(2) 0.36842(9) 0.0742(5) Uani d . 1 . . O
C20 0.52330(19) 0.6102(3) 0.37570(11) 0.0598(6) Uani d . 1 . . C
C21 0.5152(2) 0.6896(4) 0.43913(13) 0.0804(8) Uani d . 1 . . C
H21 0.4833 0.6471 0.4750 0.096 Uiso calc R 1 . . H
C22 0.5541(2) 0.8309(4) 0.44906(15) 0.0878(9) Uani d . 1 . . C
H22 0.5500 0.8834 0.4922 0.105 Uiso calc R 1 . . H
C23 0.5995(2) 0.8958(3) 0.39522(16) 0.0802(8) Uani d . 1 . . C
H23 0.6236 0.9927 0.4010 0.096 Uiso calc R 1 . . H
C24 0.60862(19) 0.8146(3) 0.33238(12) 0.0613(6) Uani d . 1 . . C
H24 0.6399 0.8581 0.2965 0.074 Uiso calc R 1 . . H
C25 0.57236(16) 0.6705(2) 0.32170(10) 0.0509(5) Uani d . 1 . . C
C26 0.58379(15) 0.5763(2) 0.25478(10) 0.0448(4) Uani d . 1 . . C
H26 0.6580 0.5264 0.2722 0.054 Uiso calc R 1 . . H
C27 0.31806(17) 0.6303(2) 0.21983(12) 0.0566(5) Uani d . 1 . . C
H27A 0.3717 0.7076 0.2397 0.085 Uiso calc R 1 . . H
H27B 0.2932 0.5886 0.2611 0.085 Uiso calc R 1 . . H
H27C 0.2531 0.6688 0.1812 0.085 Uiso calc R 1 . . H
C28 0.2908(2) 0.3907(3) 0.15310(14) 0.0659(6) Uani d . 1 . . C
H28A 0.3277 0.3169 0.1308 0.099 Uiso calc R 1 . . H
H28B 0.2257 0.4285 0.1144 0.099 Uiso calc R 1 . . H
H28C 0.2660 0.3486 0.1943 0.099 Uiso calc R 1 . . H
O29 0.77551(12) 0.7283(2) 0.22640(8) 0.0734(5) Uani d . 1 . . O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C14 O1 C2 121.31(14) y
O29 C2 O1 115.36(16) y
O29 C2 C3 125.78(17) y
O1 C2 C3 118.86(15) y
C4 C3 C2 119.17(16) ?
C4 C3 C26 121.43(16) ?
C2 C3 C26 118.84(15) ?
O15 C4 C3 124.88(16) y
O15 C4 C5 114.00(14) y
C3 C4 C5 121.11(16) ?
C14 C5 C6 118.87(16) ?
C14 C5 C4 117.83(15) ?
C6 C5 C4 123.30(16) ?
C7 C6 C5 120.21(17) ?
C7 C6 H6 119.9 ?
C5 C6 H6 119.9 ?
C6 C7 C8 121.36(16) ?
C6 C7 H7 119.3 ?
C8 C7 H7 119.3 ?
C7 C8 C9 121.94(17) ?
C7 C8 C13 119.96(16) ?
C9 C8 C13 118.10(17) ?
C10 C9 C8 120.79(18) ?
C10 C9 H9 119.6 ?
C8 C9 H9 119.6 ?
C9 C10 C11 120.95(18) ?
C9 C10 H10 119.5 ?
C11 C10 H10 119.5 ?
C12 C11 C10 120.07(19) ?
C12 C11 H11 120.0 ?
C10 C11 H11 120.0 ?
C11 C12 C13 120.43(19) ?
C11 C12 H12 119.8 ?
C13 C12 H12 119.8 ?
C12 C13 C8 119.64(16) ?
C12 C13 C14 123.58(16) ?
C8 C13 C14 116.77(16) ?
C5 C14 O1 121.47(16) y
C5 C14 C13 122.83(16) ?
O1 C14 C13 115.70(15) ?
C4 O15 C16 119.77(13) y
O15 C16 C27 106.10(15) y
O15 C16 C28 102.94(15) y
C27 C16 C28 110.00(16) ?
O15 C16 C17 108.08(13) ?
C27 C16 C17 116.39(16) ?
C28 C16 C17 112.25(17) ?
C18 C17 C26 108.12(16) ?
C18 C17 C16 116.18(15) ?
C26 C17 C16 112.90(15) ?
C18 C17 H17 106.3 ?
C26 C17 H17 106.3 ?
C16 C17 H17 106.3 ?
O19 C18 C17 114.94(17) ?
O19 C18 H18A 108.5 ?
C17 C18 H18A 108.5 ?
O19 C18 H18B 108.5 ?
C17 C18 H18B 108.5 ?
H18A C18 H18B 107.5 ?
C20 O19 C18 118.51(15) ?
O19 C20 C21 115.4(2) y
O19 C20 C25 123.34(19) y
C21 C20 C25 121.2(2) ?
C22 C21 C20 119.9(3) ?
C22 C21 H21 120.0 ?
C20 C21 H21 120.0 ?
C21 C22 C23 120.3(2) ?
C21 C22 H22 119.8 ?
C23 C22 H22 119.8 ?
C22 C23 C24 119.2(3) ?
C22 C23 H23 120.4 ?
C24 C23 H23 120.4 ?
C25 C24 C23 121.7(2) ?
C25 C24 H24 119.1 ?
C23 C24 H24 119.1 ?
C24 C25 C20 117.5(2) ?
C24 C25 C26 123.40(18) ?
C20 C25 C26 119.14(19) ?
C3 C26 C25 115.97(16) ?
C3 C26 C17 108.37(14) ?
C25 C26 C17 111.14(14) ?
C3 C26 H26 107.0 ?
C25 C26 H26 107.0 ?
C17 C26 H26 107.0 ?
C16 C27 H27A 109.5 ?
C16 C27 H27B 109.5 ?
H27A C27 H27B 109.5 ?
C16 C27 H27C 109.5 ?
H27A C27 H27C 109.5 ?
H27B C27 H27C 109.5 ?
C16 C28 H28A 109.5 ?
C16 C28 H28B 109.5 ?
H28A C28 H28B 109.5 ?
C16 C28 H28C 109.5 ?
H28A C28 H28C 109.5 ?
H28B C28 H28C 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 C14 . 1.371(2) y
O1 C2 . 1.381(2) y
C2 O29 . 1.216(2) y
C2 C3 . 1.427(2) y
C3 C4 . 1.361(2) y
C3 C26 . 1.508(2) y
C4 O15 . 1.336(2) y
C4 C5 . 1.443(2) y
C5 C14 . 1.368(2) y
C5 C6 . 1.421(2) ?
C6 C7 . 1.356(3) ?
C6 H6 . 0.93 ?
C7 C8 . 1.409(3) ?
C7 H7 . 0.93 ?
C8 C9 . 1.418(2) ?
C8 C13 . 1.420(2) ?
C9 C10 . 1.356(3) ?
C9 H9 . 0.93 ?
C10 C11 . 1.403(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.366(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.409(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.420(2) ?
O15 C16 . 1.476(2) y
C16 C27 . 1.505(3) y
C16 C28 . 1.518(3) y
C16 C17 . 1.540(3) y
C17 C18 . 1.522(3) y
C17 C26 . 1.535(3) y
C17 H17 . 0.98 ?
C18 O19 . 1.422(3) y
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
O19 C20 . 1.370(3) y
C20 C21 . 1.385(3) ?
C20 C25 . 1.395(3) ?
C21 C22 . 1.370(4) y
C21 H21 . 0.93 ?
C22 C23 . 1.382(4) ?
C22 H22 . 0.93 ?
C23 C24 . 1.388(3) ?
C23 H23 . 0.93 ?
C24 C25 . 1.385(3) ?
C24 H24 . 0.93 ?
C25 C26 . 1.523(3) y
C26 H26 . 0.98 ?
C27 H27A . 0.96 ?
C27 H27B . 0.96 ?
C27 H27C . 0.96 ?
C28 H28A . 0.96 ?
C28 H28B . 0.96 ?
C28 H28C . 0.96 ?
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
C28 H28A CgA 3_665 0.96 2.60 3.530(3) 163
C7 H7 O29 4_575 0.93 2.49 3.306(2) 147
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
C14 O1 C2 O29 174.79(19) ?
C14 O1 C2 C3 -4.6(3) ?
O29 C2 C3 C4 -173.1(2) ?
O1 C2 C3 C4 6.2(3) ?
O29 C2 C3 C26 -1.6(3) ?
O1 C2 C3 C26 177.76(17) ?
C2 C3 C4 O15 174.76(18) ?
C26 C3 C4 O15 3.4(3) ?
C2 C3 C4 C5 -4.1(3) ?
C26 C3 C4 C5 -175.5(2) y
O15 C4 C5 C14 -178.61(17) ?
C3 C4 C5 C14 0.4(3) ?
O15 C4 C5 C6 2.2(3) ?
C3 C4 C5 C6 -178.86(19) ?
C14 C5 C6 C7 -0.1(3) ?
C4 C5 C6 C7 179.11(19) ?
C5 C6 C7 C8 -0.3(3) ?
C6 C7 C8 C9 179.13(19) ?
C6 C7 C8 C13 0.2(3) ?
C7 C8 C9 C10 -178.52(19) ?
C13 C8 C9 C10 0.5(3) ?
C8 C9 C10 C11 -1.3(3) ?
C9 C10 C11 C12 1.2(3) ?
C10 C11 C12 C13 -0.3(3) ?
C11 C12 C13 C8 -0.6(3) ?
C11 C12 C13 C14 178.51(19) ?
C7 C8 C13 C12 179.47(18) ?
C9 C8 C13 C12 0.5(3) ?
C7 C8 C13 C14 0.3(3) ?
C9 C8 C13 C14 -178.64(17) ?
C6 C5 C14 O1 -179.4(2) y
C4 C5 C14 O1 1.4(3) ?
C6 C5 C14 C13 0.7(3) ?
C4 C5 C14 C13 -178.59(17) ?
C2 O1 C14 C5 0.8(3) ?
C2 O1 C14 C13 -179.22(17) ?
C12 C13 C14 C5 -179.86(19) ?
C8 C13 C14 C5 -0.8(3) ?
C12 C13 C14 O1 0.2(3) ?
C8 C13 C14 O1 179.27(16) ?
C3 C4 O15 C16 6.0(3) ?
C5 C4 O15 C16 -175.06(15) ?
C4 O15 C16 C27 90.5(2) y
C4 O15 C16 C28 -153.9(2) y
C4 O15 C16 C17 -35.0(2) ?
O15 C16 C17 C18 -177.69(16) ?
C27 C16 C17 C18 63.1(2) ?
C28 C16 C17 C18 -64.9(2) ?
O15 C16 C17 C26 56.59(19) ?
C27 C16 C17 C26 -62.6(2) ?
C28 C16 C17 C26 169.42(15) ?
C26 C17 C18 O19 55.3(2) ?
C16 C17 C18 O19 -72.8(2) ?
C17 C18 O19 C20 -35.4(3) ?
C18 O19 C20 C21 -173.70(19) ?
C18 O19 C20 C25 9.4(3) ?
O19 C20 C21 C22 -175.9(2) ?
C25 C20 C21 C22 1.0(4) ?
C20 C21 C22 C23 1.3(4) ?
C21 C22 C23 C24 -2.1(4) ?
C22 C23 C24 C25 0.7(3) ?
C23 C24 C25 C20 1.5(3) ?
C23 C24 C25 C26 -178.29(19) ?
O19 C20 C25 C24 174.3(2) y
C21 C20 C25 C24 -2.4(3) ?
O19 C20 C25 C26 -5.9(3) ?
C21 C20 C25 C26 177.44(19) ?
C4 C3 C26 C25 -107.7(2) ?
C2 C3 C26 C25 81.0(2) ?
C4 C3 C26 C17 18.1(2) ?
C2 C3 C26 C17 -153.29(17) ?
C24 C25 C26 C3 -28.5(2) ?
C20 C25 C26 C3 151.63(17) ?
C24 C25 C26 C17 -152.88(17) ?
C20 C25 C26 C17 27.3(2) ?
C18 C17 C26 C3 -177.81(15) ?
C16 C17 C26 C3 -47.87(19) ?
C18 C17 C26 C25 -49.28(19) ?
C16 C17 C26 C25 80.67(18) ?
