#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/18/1501842.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_1501842
loop_
_publ_author_name
'Fu, Peng'
'Liu, Peipei'
'Qu, Haijun'
'Wang, Yi'
'Chen, Dianfeng'
'Wang, Hui'
'Li, Jing'
'Zhu, Weiming'
_publ_section_title
;
 Α-pyrones and diketopiperazine derivatives from the marine-derived
 actinomycete Nocardiopsis dassonvillei HR10-5.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2219
_journal_page_last               2223
_journal_paper_doi               10.1021/np200597m
_journal_volume                  74
_journal_year                    2011
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.42
_chemical_name_systematic
; 
 ? 
;
_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                 123.880(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1550(8)
_cell_length_b                   25.307(2)
_cell_length_c                   12.83410(11)
_cell_measurement_reflns_used    772
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.462
_cell_measurement_theta_min      2.501
_cell_volume                     1929.3(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0608
_diffrn_reflns_av_sigmaI/netI    0.1136
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7444
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1468
_refine_ls_R_factor_gt           0.0525
_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)+(0.0050P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0882
_reflns_number_gt                1415
_reflns_number_total             3413
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np200597m_si_002.cif
_cod_data_source_block           101029f
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1501842
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
N1 N 0.4334(5) 0.91187(9) 0.3223(2) 0.0458(8) Uani 1 1 d .
N2 N 0.7664(5) 0.83327(9) 0.4101(2) 0.0435(7) Uani 1 1 d .
O1 O 0.7015(4) 0.97467(8) 0.4227(2) 0.0737(8) Uani 1 1 d .
O2 O 0.4919(4) 0.77051(8) 0.3277(2) 0.0530(7) Uani 1 1 d .
O3 O -0.6992(4) 0.93703(9) -0.1029(3) 0.0797(8) Uani 1 1 d .
O4 O 1.8512(5) 0.78778(8) 0.6926(2) 0.0744(8) Uani 1 1 d .
C1 C 0.3652(6) 0.85858(12) 0.2834(3) 0.0419(9) Uani 1 1 d .
C2 C 0.5587(6) 0.82152(12) 0.3475(3) 0.0413(9) Uani 1 1 d .
C3 C 0.8294(6) 0.88670(12) 0.4299(3) 0.0426(9) Uani 1 1 d .
C4 C 0.6549(6) 0.92832(13) 0.3923(3) 0.0495(10) Uani 1 1 d .
C5 C 0.2667(5) 0.95187(11) 0.3009(3) 0.0611(11) Uani 1 1 d .
H5A H 0.3355 0.9770 0.3684 0.092 Uiso 1 1 calc R
H5B H 0.1431 0.9350 0.2974 0.092 Uiso 1 1 calc R
H5C H 0.2125 0.9697 0.2231 0.092 Uiso 1 1 calc R
C6 C 0.1565(6) 0.84142(12) 0.2032(3) 0.0517(10) Uani 1 1 d .
H6 H 0.1452 0.8048 0.1971 0.062 Uiso 1 1 calc R
C7 C -0.0611(6) 0.86874(12) 0.1219(3) 0.0479(10) Uani 1 1 d .
C8 C -0.1060(6) 0.90369(13) 0.0280(3) 0.0610(11) Uani 1 1 d .
H8 H 0.0078 0.9116 0.0161 0.073 Uiso 1 1 calc R
C9 C -0.3151(7) 0.92740(12) -0.0492(3) 0.0630(11) Uani 1 1 d .
H9 H -0.3395 0.9508 -0.1115 0.076 Uiso 1 1 calc R
C10 C -0.4861(6) 0.91623(14) -0.0336(4) 0.0559(10) Uani 1 1 d .
C11 C -0.4464(6) 0.88053(14) 0.0591(4) 0.0598(11) Uani 1 1 d .
H11 H -0.5606 0.8725 0.0706 0.072 Uiso 1 1 calc R
C12 C -0.2377(6) 0.85703(12) 0.1341(3) 0.0530(10) Uani 1 1 d .
H12 H -0.2148 0.8327 0.1944 0.064 Uiso 1 1 calc R
C13 C -0.7521(7) 0.97150(13) -0.2048(4) 0.0949(15) Uani 1 1 d .
H13A H -0.6539 1.0016 -0.1727 0.142 Uiso 1 1 calc R
H13B H -0.9055 0.9831 -0.2467 0.142 Uiso 1 1 calc R
H13C H -0.7322 0.9529 -0.2631 0.142 Uiso 1 1 calc R
C14 C 1.0440(6) 0.90185(11) 0.4858(3) 0.0479(9) Uani 1 1 d .
H14 H 1.0661 0.9382 0.4941 0.057 Uiso 1 1 calc R
C15 C 1.2494(6) 0.87080(12) 0.5359(3) 0.0432(9) Uani 1 1 d .
C16 C 1.2581(6) 0.81578(12) 0.5271(3) 0.0526(10) Uani 1 1 d .
H16 H 1.1251 0.7964 0.4855 0.063 Uiso 1 1 calc R
C17 C 1.4600(6) 0.79016(12) 0.5791(3) 0.0543(10) Uani 1 1 d .
H17 H 1.4627 0.7536 0.5733 0.065 Uiso 1 1 calc R
C18 C 1.6585(6) 0.81801(14) 0.6399(3) 0.0486(10) Uani 1 1 d .
C19 C 1.6589(6) 0.87194(12) 0.6506(3) 0.0530(10) Uani 1 1 d .
H19 H 1.7933 0.8908 0.6926 0.064 Uiso 1 1 calc R
C20 C 1.4553(6) 0.89750(12) 0.5974(3) 0.0517(10) Uani 1 1 d .
H20 H 1.4548 0.9341 0.6027 0.062 Uiso 1 1 calc R
C21 C 2.0676(6) 0.81437(15) 0.7646(4) 0.1048(16) Uani 1 1 d .
H21A H 2.0836 0.8372 0.7103 0.157 Uiso 1 1 calc R
H21B H 2.1860 0.7886 0.8010 0.157 Uiso 1 1 calc R
H21C H 2.0763 0.8349 0.8301 0.157 Uiso 1 1 calc R
C22 C 0.6720(6) 0.73207(10) 0.3935(3) 0.0600(11) Uani 1 1 d .
H22A H 0.7751 0.7361 0.3684 0.090 Uiso 1 1 calc R
H22B H 0.6098 0.6971 0.3731 0.090 Uiso 1 1 calc R
H22C H 0.7503 0.7376 0.4823 0.090 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'
N N 0.0061 0.0033 '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
C4 N1 C1 123.9(3)
C4 N1 C5 115.6(3)
C1 N1 C5 120.2(3)
C2 N2 C3 119.0(3)
C2 O2 C22 115.1(3)
C10 O3 C13 117.1(3)
C18 O4 C21 118.3(3)
C6 C1 N1 126.7(3)
C6 C1 C2 121.4(3)
N1 C1 C2 111.9(3)
N2 C2 O2 120.6(3)
N2 C2 C1 127.2(3)
O2 C2 C1 112.1(3)
C14 C3 N2 122.0(3)
C14 C3 C4 118.3(3)
N2 C3 C4 119.7(3)
O1 C4 N1 120.5(3)
O1 C4 C3 122.9(3)
N1 C4 C3 116.6(3)
N1 C5 H5A 109.5
N1 C5 H5B 109.5
H5A C5 H5B 109.5
N1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C1 C6 C7 133.0(3)
C1 C6 H6 113.5
C7 C6 H6 113.5
C8 C7 C12 116.8(3)
C8 C7 C6 123.9(4)
C12 C7 C6 119.2(3)
C7 C8 C9 122.3(4)
C7 C8 H8 118.9
C9 C8 H8 118.9
C10 C9 C8 120.0(4)
C10 C9 H9 120.0
C8 C9 H9 120.0
O3 C10 C9 125.8(4)
O3 C10 C11 115.2(4)
C9 C10 C11 119.0(4)
C12 C11 C10 120.1(4)
C12 C11 H11 120.0
C10 C11 H11 120.0
C11 C12 C7 121.9(3)
C11 C12 H12 119.1
C7 C12 H12 119.1
O3 C13 H13A 109.5
O3 C13 H13B 109.5
H13A C13 H13B 109.5
O3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C3 C14 C15 130.8(3)
C3 C14 H14 114.6
C15 C14 H14 114.6
C20 C15 C16 116.5(3)
C20 C15 C14 118.2(3)
C16 C15 C14 125.3(3)
C17 C16 C15 120.9(3)
C17 C16 H16 119.6
C15 C16 H16 119.6
C16 C17 C18 120.6(3)
C16 C17 H17 119.7
C18 C17 H17 119.7
C19 C18 C17 120.8(3)
C19 C18 O4 123.8(3)
C17 C18 O4 115.3(3)
C18 C19 C20 118.4(3)
C18 C19 H19 120.8
C20 C19 H19 120.8
C19 C20 C15 122.9(3)
C19 C20 H20 118.5
C15 C20 H20 118.5
O4 C21 H21A 109.5
O4 C21 H21B 109.5
H21A C21 H21B 109.5
O4 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
O2 C22 H22A 109.5
O2 C22 H22B 109.5
H22A C22 H22B 109.5
O2 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C4 1.380(4)
N1 C1 1.426(3)
N1 C5 1.469(3)
N2 C2 1.270(4)
N2 C3 1.403(3)
O1 C4 1.222(3)
O2 C2 1.351(3)
O2 C22 1.452(3)
O3 C10 1.372(4)
O3 C13 1.437(4)
O4 C18 1.380(4)
O4 C21 1.452(4)
C1 C6 1.328(4)
C1 C2 1.484(4)
C3 C14 1.338(4)
C3 C4 1.493(4)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 C7 1.477(4)
C6 H6 0.9300
C7 C8 1.381(4)
C7 C12 1.389(4)
C8 C9 1.388(4)
C8 H8 0.9300
C9 C10 1.375(5)
C9 H9 0.9300
C10 C11 1.392(4)
C11 C12 1.381(4)
C11 H11 0.9300
C12 H12 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 C15 1.462(4)
C14 H14 0.9300
C15 C20 1.397(4)
C15 C16 1.401(3)
C16 C17 1.370(4)
C16 H16 0.9300
C17 C18 1.374(4)
C17 H17 0.9300
C18 C19 1.371(4)
C19 C20 1.378(4)
C19 H19 0.9300
C20 H20 0.9300
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
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
C4 N1 C1 C6 -170.8(4)
C5 N1 C1 C6 16.4(5)
C4 N1 C1 C2 11.3(4)
C5 N1 C1 C2 -161.5(3)
C3 N2 C2 O2 -179.3(2)
C3 N2 C2 C1 4.0(5)
C22 O2 C2 N2 6.1(4)
C22 O2 C2 C1 -176.7(3)
C6 C1 C2 N2 168.4(4)
N1 C1 C2 N2 -13.6(5)
C6 C1 C2 O2 -8.6(5)
N1 C1 C2 O2 169.5(2)
C2 N2 C3 C14 -174.2(3)
C2 N2 C3 C4 8.1(4)
C1 N1 C4 O1 -179.8(3)
C5 N1 C4 O1 -6.7(5)
C1 N1 C4 C3 -1.1(5)
C5 N1 C4 C3 172.0(3)
C14 C3 C4 O1 -8.5(5)
N2 C3 C4 O1 169.2(3)
C14 C3 C4 N1 172.8(3)
N2 C3 C4 N1 -9.5(5)
N1 C1 C6 C7 6.6(7)
C2 C1 C6 C7 -175.7(4)
C1 C6 C7 C8 60.5(6)
C1 C6 C7 C12 -123.3(4)
C12 C7 C8 C9 1.7(5)
C6 C7 C8 C9 177.9(3)
C7 C8 C9 C10 -0.1(6)
C13 O3 C10 C9 3.3(5)
C13 O3 C10 C11 -176.2(3)
C8 C9 C10 O3 179.7(3)
C8 C9 C10 C11 -0.8(6)
O3 C10 C11 C12 179.7(3)
C9 C10 C11 C12 0.2(5)
C10 C11 C12 C7 1.4(5)
C8 C7 C12 C11 -2.3(5)
C6 C7 C12 C11 -178.7(3)
N2 C3 C14 C15 0.2(6)
C4 C3 C14 C15 177.9(3)
C3 C14 C15 C20 -175.9(4)
C3 C14 C15 C16 4.4(6)
C20 C15 C16 C17 1.3(5)
C14 C15 C16 C17 -178.9(3)
C15 C16 C17 C18 -0.7(6)
C16 C17 C18 C19 0.5(6)
C16 C17 C18 O4 177.6(3)
C21 O4 C18 C19 0.6(5)
C21 O4 C18 C17 -176.5(3)
C17 C18 C19 C20 -0.9(5)
O4 C18 C19 C20 -177.7(3)
C18 C19 C20 C15 1.6(5)
C16 C15 C20 C19 -1.8(5)
C14 C15 C20 C19 178.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26616175
