#------------------------------------------------------------------------------
#$Date: 2019-11-23 17:05:32 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234119 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/33/1553334.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_1553334
loop_
_publ_author_name
'Cai, Runlin'
'Wu, Yingnan'
'Chen, Senhua'
'Cui, Hui'
'Liu, Zhaoming'
'Li, Chunyuan'
'She, Zhigang'
_publ_section_title
;
 Peniisocoumarins A-J: Isocoumarins from Penicillium commune QQF-3, an
 Endophytic Fungus of the Mangrove Plant Kandelia candel.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1376
_journal_page_last               1383
_journal_paper_doi               10.1021/acs.jnatprod.7b01018
_journal_volume                  81
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H13 Cl O5'
_chemical_formula_sum            'C13 H13 Cl O5'
_chemical_formula_weight         284.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.302(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.0660(6)
_cell_length_b                   9.1694(3)
_cell_length_c                   6.5996(2)
_cell_measurement_reflns_used    6397
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6430
_cell_measurement_theta_min      5.2410
_cell_volume                     1274.89(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9242
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.025
_diffrn_reflns_theta_min         4.197
_exptl_absorpt_coefficient_mu    2.804
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.021
_exptl_crystal_size_mid          0.019
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2499
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0682P)²+0.5673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                2478
_reflns_number_total             2499
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np7b01018_si_005.cif
_cod_data_source_block           aa
_cod_database_code               1553334
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2'(H2')
2.b Secondary CH2 refined with riding coordinates:
 C1'(H1'A,H1'B), C3'(H3'A,H3'B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Cl1 Cl -0.36349(3) -0.79650(9) -0.45956(10) 0.0320(2) Uani 1 1 d .
O4 O -0.66754(8) -1.2988(3) -0.4051(3) 0.0270(4) Uani 1 1 d .
O2 O -0.37903(9) -1.1158(2) -0.1153(3) 0.0234(4) Uani 1 1 d .
O1 O -0.36551(9) -1.3525(2) -0.1317(3) 0.0263(4) Uani 1 1 d .
C6 C -0.60323(11) -1.2974(4) -0.3465(3) 0.0213(5) Uani 1 1 d .
C7 C -0.56570(13) -1.4223(3) -0.3127(4) 0.0226(5) Uani 1 1 d .
H7 H -0.5842 -1.5144 -0.3303 0.027 Uiso 1 1 calc R
C8A C -0.47193(12) -1.2675(3) -0.2236(4) 0.0200(5) Uani 1 1 d .
C4A C -0.51114(12) -1.1424(3) -0.2592(4) 0.0194(5) Uani 1 1 d .
C5 C -0.57650(12) -1.1579(3) -0.3224(4) 0.0214(5) Uani 1 1 d .
H5 H -0.6025 -1.0759 -0.3487 0.026 Uiso 1 1 calc R
C8 C -0.49997(13) -1.4071(3) -0.2520(4) 0.0210(5) Uani 1 1 d .
O5 O -0.46455(9) -1.5295(2) -0.2214(3) 0.0279(4) Uani 1 1 d .
H5A H -0.4268 -1.5077 -0.1803 0.042 Uiso 1 1 calc GR
C4 C -0.48022(12) -1.0023(3) -0.2204(4) 0.0219(5) Uani 1 1 d .
H4 H -0.5045 -0.9176 -0.2482 0.026 Uiso 1 1 calc R
O3 O -0.25581(10) -0.7260(3) 0.1338(4) 0.0363(5) Uani 1 1 d .
H3 H -0.2209 -0.7641 0.1544 0.055 Uiso 1 1 calc GR
C1 C -0.40410(12) -1.2522(3) -0.1568(4) 0.0214(5) Uani 1 1 d .
C3 C -0.41699(12) -0.9925(3) -0.1450(4) 0.0227(5) Uani 1 1 d .
C2' C -0.32664(12) -0.8344(3) -0.1802(4) 0.0243(5) Uani 1 1 d .
H2' H -0.3006 -0.9225 -0.1657 0.029 Uiso 1 1 calc R
C1' C -0.37832(12) -0.8592(3) -0.0738(5) 0.0258(6) Uani 1 1 d .
H1'A H -0.3586 -0.8652 0.0784 0.031 Uiso 1 1 calc R
H1'B H -0.4064 -0.7753 -0.1011 0.031 Uiso 1 1 calc R
C3' C -0.28408(13) -0.7051(3) -0.0866(5) 0.0271(6) Uani 1 1 d .
H3'A H -0.2513 -0.6953 -0.1562 0.033 Uiso 1 1 calc R
H3'B H -0.3090 -0.6162 -0.1105 0.033 Uiso 1 1 calc R
C9 C -0.69863(13) -1.4371(3) -0.4313(5) 0.0329(7) Uani 1 1 d .
H9A H -0.6860 -1.4935 -0.5345 0.049 Uiso 1 1 calc GR
H9B H -0.7438 -1.4229 -0.4788 0.049 Uiso 1 1 calc GR
H9C H -0.6870 -1.4880 -0.2981 0.049 Uiso 1 1 calc GR
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'
Cl Cl 0.3639 0.7018 '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
C6 O4 C9 117.9(2)
C1 O2 C3 121.9(2)
O4 C6 C7 124.0(3)
O4 C6 C5 114.3(3)
C7 C6 C5 121.6(2)
C8 C7 C6 118.8(3)
C4A C8A C1 120.2(2)
C8 C8A C4A 119.5(2)
C8 C8A C1 120.4(2)
C8A C4A C4 117.4(2)
C5 C4A C8A 119.9(2)
C5 C4A C4 122.7(2)
C4A C5 C6 119.6(2)
C7 C8 C8A 120.5(2)
O5 C8 C7 117.9(2)
O5 C8 C8A 121.6(2)
C3 C4 C4A 120.8(2)
O2 C1 C8A 118.4(2)
O1 C1 O2 115.8(2)
O1 C1 C8A 125.8(2)
O2 C3 C1' 111.1(2)
C4 C3 O2 121.2(3)
C4 C3 C1' 127.6(2)
C1' C2' Cl1 109.05(18)
C1' C2' C3' 112.6(2)
C3' C2' Cl1 107.39(19)
C3 C1' C2' 114.6(2)
O3 C3' C2' 110.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2' 1.814(3)
O4 C6 1.355(3)
O4 C9 1.428(4)
O2 C1 1.362(3)
O2 C3 1.386(3)
O1 C1 1.231(3)
C6 C7 1.392(4)
C6 C5 1.398(4)
C7 C8 1.392(4)
C8A C4A 1.414(3)
C8A C8 1.409(4)
C8A C1 1.436(3)
C4A C5 1.384(3)
C4A C4 1.442(4)
C8 O5 1.348(3)
C4 C3 1.338(4)
O3 C3' 1.415(4)
C3 C1' 1.484(4)
C2' C1' 1.524(4)
C2' C3' 1.524(4)
