#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/65/2006578.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_2006578
loop_
_publ_author_name
'Zukerman-Schpector, J.'
'Castellano, E.E.'
'Ceschi, Marco Antonio'
'Brocksom, Timothy John'
'Wikaira, Jan L.'
_publ_section_title
;
 Intermediates in the Synthesis of Daphniphyllum Alkaloids. I. A
 Tetracyclic Oxygen Analogue
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1482
_journal_page_last               1483
_journal_paper_doi               10.1107/S0108270197005222
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C20 H25 Br1 O4'
_chemical_formula_sum            'C20 H25 Br O4'
_chemical_formula_weight         409.319
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           'manual editing of SHELXL93.CIF'
_cell_angle_alpha                90
_cell_angle_beta                 94.400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9210(9)
_cell_length_b                   10.6680(10)
_cell_length_c                   10.7280(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.35
_cell_measurement_theta_min      9.54
_cell_volume                     903.86(16)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1995)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω/-2θ
_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  0.023
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2402
_diffrn_reflns_theta_max         27.97
_diffrn_standards_decay_%        0.8
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.296
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_correction_T_min  0.584
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   '(PLATON; Spek, 1990)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.5040
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             424.0
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.775
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.077
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2288
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_restrained_S_obs      1.159
_refine_ls_R_factor_all          0.092
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0376P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.117
_refine_ls_wR_factor_ref         0.098
_reflns_number_gt                1473
_reflns_number_total             2288
_reflns_threshold_expression     'F² > 2\sF²'
_cod_data_source_file            fg1310.cif
_cod_data_source_block           default
_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.

'_exptl_absorpt_correction_type' value 'Gaussian'
changed to 'gaussian' 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:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0376P)^2^] where P = (Fo^2^+2Fc^2^)/3' was changed
to 'calc'. New tag '_refine_ls_weighting_details' was created. The
value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0376P)^2^]
where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C20 H25 Br1 O4'
_cod_database_code               2006578
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
Br .21492(9) -.00004(8) .76167(5) .0606(3) Uani d . 1 . Br
O1 .0353(6) -.1236(4) 1.0275(4) .0431(11) Uani d . 1 . O
O2 .4424(5) -.0346(4) 1.1974(4) .0421(11) Uani d . 1 . O
O3 .2500(7) .0770(5) 1.4382(4) .0596(14) Uani d . 1 . O
O4 .1255(5) .2422(4) 1.3458(4) .0417(10) Uani d . 1 . O
C1 .2663(7) .1210(6) .9943(5) .0280(12) Uani d . 1 . C
C2 .1609(8) .0483(5) .9249(5) .0336(14) Uani d . 1 . C
C3 -.0022(7) -.0052(7) .9637(4) .0360(13) Uani d . 1 . C
H3 -.0795(7) -.0200(7) .8894(4) .043 Uiso calc R 1 . H
C4 -.0892(7) .0745(6) 1.0557(5) .0342(13) Uani d . 1 . C
H4A -.2110(7) .0634(6) 1.0459(5) .041 Uiso calc R 1 . H
H4B -.0628(7) .1626(6) 1.0458(5) .041 Uiso calc R 1 . H
C5 -.0150(6) .0244(6) 1.1835(5) .0288(12) Uani d . 1 . C
C6 -.0223(7) -.1160(6) 1.1512(5) .0335(13) Uani d . 1 . C
H6 -.1403(7) -.1442(6) 1.1486(5) .040 Uiso calc R 1 . H
C7 .0837(7) -.1998(6) 1.2363(5) .0339(13) Uani d . 1 . C
H7 .0410(7) -.2762(6) 1.2611(5) .041 Uiso calc R 1 . H
C8 .2388(7) -.1651(6) 1.2764(5) .0299(12) Uani d . 1 . C
C9 .2989(7) -.0446(5) 1.2280(5) .0303(13) Uani d . 1 . C
C10 .1753(7) .0682(5) 1.2161(5) .0263(11) Uani d . 1 . C
C11 .2356(7) .1688(5) 1.1245(5) .0274(11) Uani d . 1 . C
H11 .1456(7) .2318(5) 1.1140(5) .033 Uiso calc R 1 . H
C12 .4022(7) .2400(6) 1.1671(5) .0361(14) Uani d . 1 . C
H12A .3788(7) .3118(6) 1.2186(5) .043 Uiso calc R 1 . H
H12B .4815(7) .1852(6) 1.2139(5) .043 Uiso calc R 1 . H
C13 .4718(8) .2816(7) 1.0451(6) .046(2) Uani d . 1 . C
H13A .4187(8) .3589(7) 1.0150(6) .055 Uiso calc R 1 . H
H13B .5933(8) .2942(7) 1.0561(6) .055 Uiso calc R 1 . H
C14 .4287(8) .1753(7) .9554(6) .043(2) Uani d . 1 . C
H14A .4143(8) .2060(7) .8701(6) .052 Uiso calc R 1 . H
H14B .5177(8) .1126(7) .9608(6) .052 Uiso calc R 1 . H
C15 -.1368(8) .0519(7) 1.2864(6) .046(2) Uani d . 1 . C
H15A -.154(5) .1407(7) 1.292(3) .069 Uiso calc R 1 . H
H15B -.088(3) .021(4) 1.3652(11) .069 Uiso calc R 1 . H
H15C -.243(2) .011(4) 1.266(3) .069 Uiso calc R 1 . H
C16 .1890(7) .1270(6) 1.3463(5) .0320(13) Uani d . 1 . C
C17 .1283(10) .3057(8) 1.4651(7) .062(2) Uani d . 1 . C
H17A .094(7) .3912(16) 1.4522(8) .093 Uiso calc R 1 . H
H17B .2409(19) .303(5) 1.505(3) .093 Uiso calc R 1 . H
H17C .052(6) .265(3) 1.517(2) .093 Uiso calc R 1 . H
C18 .3645(8) -.2456(6) 1.3559(5) .0372(14) Uani d . 1 . C
H18 .4752(8) -.2356(6) 1.3220(5) .045 Uiso calc R 1 . H
C19 .3226(11) -.3836(8) 1.3516(8) .070(2) Uani d . 1 . C
H19A .413(3) -.4299(9) 1.395(5) .104 Uiso calc R 1 . H
H19B .309(7) -.4110(14) 1.2662(9) .104 Uiso calc R 1 . H
H19C .219(4) -.3978(10) 1.391(5) .104 Uiso calc R 1 . H
C20 .3830(10) -.2009(8) 1.4914(6) .060(2) Uani d . 1 . C
H20A .428(7) -.117(2) 1.4947(8) .090 Uiso calc R 1 . H
H20B .458(6) -.256(3) 1.5397(13) .090 Uiso calc R 1 . H
H20C .2741(15) -.201(5) 1.5250(18) .090 Uiso calc R 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 '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'
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'
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 O1 C3 108.5(4) yes
C16 O4 C17 116.7(5) no
C2 C1 C14 125.9(5) yes
C2 C1 C11 124.9(5) yes
C14 C1 C11 109.1(5) yes
C1 C2 C3 125.9(5) yes
C1 C2 Br 119.9(4) yes
C3 C2 Br 114.2(4) yes
O1 C3 C2 108.1(4) no
O1 C3 C4 105.6(4) no
C2 C3 C4 114.4(5) no
C3 C4 C5 102.9(4) no
C6 C5 C4 97.6(4) no
C6 C5 C15 109.3(5) no
C4 C5 C15 110.6(5) no
C6 C5 C10 110.7(5) no
C4 C5 C10 112.5(4) no
C15 C5 C10 114.8(4) no
O1 C6 C7 109.1(5) no
O1 C6 C5 104.7(5) no
C7 C6 C5 115.9(5) no
C8 C7 C6 119.9(5) no
C7 C8 C9 116.4(5) yes
C7 C8 C18 125.1(6) yes
C9 C8 C18 118.2(5) yes
O2 C9 C8 120.4(5) no
O2 C9 C10 120.6(5) no
C8 C9 C10 119.1(5) no
C16 C10 C9 104.1(4) no
C16 C10 C11 106.9(5) no
C9 C10 C11 111.4(4) no
C16 C10 C5 108.7(4) no
C9 C10 C5 111.8(5) no
C11 C10 C5 113.3(4) no
C1 C11 C10 115.3(5) no
C1 C11 C12 103.9(4) no
C10 C11 C12 116.4(4) no
C13 C12 C11 104.1(5) no
C14 C13 C12 104.5(6) no
C1 C14 C13 105.7(5) no
O3 C16 O4 123.3(5) no
O3 C16 C10 124.7(6) no
O4 C16 C10 112.1(5) no
C19 C18 C8 113.5(6) no
C19 C18 C20 109.8(6) no
C8 C18 C20 111.6(5) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br C2 1.906(5) yes
O1 C6 1.439(7) yes
O1 C3 1.457(8) yes
O2 C9 1.212(7) yes
O3 C16 1.190(7) no
O4 C16 1.327(8) no
O4 C17 1.446(8) no
C1 C2 1.325(8) yes
C1 C14 1.499(8) yes
C1 C11 1.523(7) yes
C2 C3 1.500(8) yes
C3 C4 1.508(9) no
C4 C5 1.545(7) no
C5 C6 1.538(9) no
C5 C15 1.549(8) no
C5 C10 1.591(7) no
C6 C7 1.489(8) no
C7 C8 1.323(8) yes
C8 C9 1.479(8) yes
C8 C18 1.524(8) yes
C9 C10 1.551(8) no
C10 C16 1.528(8) no
C10 C11 1.555(8) no
C11 C12 1.561(7) no
C12 C13 1.525(9) no
C13 C14 1.509(10) no
C18 C19 1.510(10) no
C18 C20 1.526(9) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21186260
