#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/28/1502820.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_1502820
loop_
_publ_author_name
'Pettit, George R.'
'Meng, Yanhui'
'Pettit, Robin K.'
'Herald, Delbert L.'
'Cichacz, Zbigniew A.'
'Doubek, Dennis L.'
'Richert, Linda'
_publ_section_title
;
 Antineoplastic agents. 556. Isolation and structure of Coprinastatin 1
 from Coprinus cinereus.
;
_journal_issue                   3
_journal_name_full               'Journal of natural products'
_journal_page_first              388
_journal_page_last               392
_journal_paper_doi               10.1021/np900371j
_journal_volume                  73
_journal_year                    2010
_chemical_formula_sum            'C9 H7 N O3'
_chemical_formula_weight         177.16
_chemical_name_common            'Compound 5'
_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                 100.8540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.7251(2)
_cell_length_b                   10.7734(3)
_cell_length_c                   16.5954(4)
_cell_measurement_reflns_used    5195
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      69.31
_cell_measurement_theta_min      4.92
_cell_volume                     1532.04(7)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11007
_diffrn_reflns_theta_full        69.57
_diffrn_reflns_theta_max         69.57
_diffrn_reflns_theta_min         4.92
_exptl_absorpt_coefficient_mu    0.991
_exptl_absorpt_correction_T_max  0.9423
_exptl_absorpt_correction_T_min  0.7557
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS-Acta Cryst. A51, 33-35 (1995)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_description       'Thin needles'
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           'Full-matrix least-squares'
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0332
_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)+(0.0452P)²+0.5193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0887
_reflns_number_gt                2541
_reflns_number_total             2841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np900371j_si_006.cif
_cod_data_source_block           p21overc
_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 2.4.2 from
2011-04-26.

'_atom_sites_solution_hydrogens' value 'Geom' changed to
'geom' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_atom_sites_solution_secondary' value 'Difmap' changed
to 'difmap' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'Constr' changed
to 'constr' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_weighting_scheme' value 'Calc' changed to
'calc' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

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 'not measured' 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      P2(1)/c
_cod_database_code               1502820
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
C1_1 C 0.05766(14) 0.34367(12) 0.12358(7) 0.0200(3) Uani 1 1 d .
C2_1 C 0.16211(14) 0.32054(12) 0.19762(8) 0.0215(3) Uani 1 1 d .
H2A_1 H 0.1629 0.3738 0.2418 0.026 Uiso 1 1 calc R
C3_1 C 0.26366(15) 0.22065(12) 0.20637(8) 0.0231(3) Uani 1 1 d .
H3A_1 H 0.3313 0.2085 0.2562 0.028 Uiso 1 1 calc R
C4_1 C 0.26668(15) 0.13790(12) 0.14221(8) 0.0240(3) Uani 1 1 d .
H4A_1 H 0.3343 0.0704 0.1479 0.029 Uiso 1 1 calc R
C4A_1 C 0.16436(15) 0.16123(12) 0.07006(8) 0.0218(3) Uani 1 1 d .
O5_1 O 0.14475(11) 0.09343(8) -0.00236(6) 0.0261(2) Uani 1 1 d .
C6_1 C 0.02736(16) 0.15126(13) -0.05813(8) 0.0255(3) Uani 1 1 d .
O6_1 O -0.01593(13) 0.11291(10) -0.12672(6) 0.0339(3) Uani 1 1 d .
C7A_1 C 0.06165(14) 0.26010(12) 0.05989(8) 0.0201(3) Uani 1 1 d .
N7_1 N -0.02230(13) 0.25129(10) -0.01973(6) 0.0229(2) Uani 1 1 d .
H7A_1 H -0.0949 0.3015 -0.0416 0.027 Uiso 1 1 calc R
C8_1 C -0.05251(14) 0.44891(12) 0.11101(8) 0.0217(3) Uani 1 1 d .
O8_1 O -0.14158(11) 0.45844(9) 0.04462(5) 0.0268(2) Uani 1 1 d .
C9_1 C -0.05136(16) 0.54260(13) 0.17745(8) 0.0256(3) Uani 1 1 d .
H9A_1 H -0.1296 0.6044 0.1594 0.038 Uiso 1 1 calc R
H9B_1 H 0.0493 0.5815 0.1900 0.038 Uiso 1 1 calc R
H9C_1 H -0.0731 0.5022 0.2256 0.038 Uiso 1 1 calc R
C1_2 C 0.54799(14) 0.26014(12) 0.04045(8) 0.0215(3) Uani 1 1 d .
C2_2 C 0.66896(15) 0.18591(13) 0.08347(8) 0.0255(3) Uani 1 1 d .
H2A_2 H 0.7048 0.1190 0.0568 0.031 Uiso 1 1 calc R
C3_2 C 0.73610(16) 0.20967(14) 0.16440(9) 0.0296(3) Uani 1 1 d .
H3A_2 H 0.8149 0.1577 0.1908 0.035 Uiso 1 1 calc R
C4_2 C 0.68865(16) 0.30979(14) 0.20746(8) 0.0282(3) Uani 1 1 d .
H4A_2 H 0.7336 0.3261 0.2618 0.034 Uiso 1 1 calc R
C4A_2 C 0.57189(15) 0.38247(12) 0.16476(8) 0.0231(3) Uani 1 1 d .
O5_2 O 0.50204(11) 0.48542(9) 0.19275(5) 0.0252(2) Uani 1 1 d .
C6_2 C 0.38679(15) 0.52571(12) 0.12873(8) 0.0222(3) Uani 1 1 d .
O6_2 O 0.30454(11) 0.61415(9) 0.13489(6) 0.0280(2) Uani 1 1 d .
C7A_2 C 0.50163(14) 0.35950(12) 0.08392(8) 0.0205(3) Uani 1 1 d .
N7_2 N 0.38837(12) 0.44956(10) 0.06359(6) 0.0206(2) Uani 1 1 d .
H7A_2 H 0.3277 0.4565 0.0166 0.025 Uiso 1 1 calc R
C8_2 C 0.46919(15) 0.23689(12) -0.04509(8) 0.0227(3) Uani 1 1 d .
O8_2 O 0.36131(11) 0.30336(9) -0.07711(6) 0.0285(2) Uani 1 1 d .
C9_2 C 0.52333(17) 0.13069(13) -0.09118(9) 0.0291(3) Uani 1 1 d .
H9A_2 H 0.4616 0.1272 -0.1455 0.044 Uiso 1 1 calc R
H9B_2 H 0.5120 0.0544 -0.0630 0.044 Uiso 1 1 calc R
H9C_2 H 0.6310 0.1425 -0.0945 0.044 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 0.0181 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'
N N 0.0311 0.0180 '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
C7A_1 C1_1 C2_1 116.31(12)
C7A_1 C1_1 C8_1 119.86(11)
C2_1 C1_1 C8_1 123.84(12)
C3_1 C2_1 C1_1 121.71(12)
C3_1 C2_1 H2A_1 119.1
C1_1 C2_1 H2A_1 119.1
C2_1 C3_1 C4_1 121.43(12)
C2_1 C3_1 H3A_1 119.3
C4_1 C3_1 H3A_1 119.3
C4A_1 C4_1 C3_1 116.48(12)
C4A_1 C4_1 H4A_1 121.8
C3_1 C4_1 H4A_1 121.8
C4_1 C4A_1 C7A_1 123.17(12)
C4_1 C4A_1 O5_1 127.67(12)
C7A_1 C4A_1 O5_1 109.16(11)
C4A_1 O5_1 C6_1 107.18(10)
O6_1 C6_1 N7_1 130.01(13)
O6_1 C6_1 O5_1 122.42(13)
N7_1 C6_1 O5_1 107.56(11)
C4A_1 C7A_1 N7_1 106.11(11)
C4A_1 C7A_1 C1_1 120.90(12)
N7_1 C7A_1 C1_1 132.99(12)
C6_1 N7_1 C7A_1 109.99(11)
C6_1 N7_1 H7A_1 125.0
C7A_1 N7_1 H7A_1 125.0
O8_1 C8_1 C1_1 118.47(12)
O8_1 C8_1 C9_1 121.42(12)
C1_1 C8_1 C9_1 120.09(11)
C8_1 C9_1 H9A_1 109.5
C8_1 C9_1 H9B_1 109.5
H9A_1 C9_1 H9B_1 109.5
C8_1 C9_1 H9C_1 109.5
H9A_1 C9_1 H9C_1 109.5
H9B_1 C9_1 H9C_1 109.5
C7A_2 C1_2 C2_2 115.93(12)
C7A_2 C1_2 C8_2 120.00(11)
C2_2 C1_2 C8_2 124.06(12)
C3_2 C2_2 C1_2 121.82(13)
C3_2 C2_2 H2A_2 119.1
C1_2 C2_2 H2A_2 119.1
C2_2 C3_2 C4_2 121.76(13)
C2_2 C3_2 H3A_2 119.1
C4_2 C3_2 H3A_2 119.1
C4A_2 C4_2 C3_2 116.03(12)
C4A_2 C4_2 H4A_2 122.0
C3_2 C4_2 H4A_2 122.0
C4_2 C4A_2 O5_2 127.88(12)
C4_2 C4A_2 C7A_2 123.19(13)
O5_2 C4A_2 C7A_2 108.92(11)
C4A_2 O5_2 C6_2 107.13(10)
O6_2 C6_2 N7_2 129.66(12)
O6_2 C6_2 O5_2 122.54(11)
N7_2 C6_2 O5_2 107.80(11)
N7_2 C7A_2 C4A_2 106.04(11)
N7_2 C7A_2 C1_2 132.68(12)
C4A_2 C7A_2 C1_2 121.27(12)
C6_2 N7_2 C7A_2 110.11(10)
C6_2 N7_2 H7A_2 124.9
C7A_2 N7_2 H7A_2 124.9
O8_2 C8_2 C1_2 119.97(12)
O8_2 C8_2 C9_2 121.05(12)
C1_2 C8_2 C9_2 118.99(11)
C8_2 C9_2 H9A_2 109.5
C8_2 C9_2 H9B_2 109.5
H9A_2 C9_2 H9B_2 109.5
C8_2 C9_2 H9C_2 109.5
H9A_2 C9_2 H9C_2 109.5
H9B_2 C9_2 H9C_2 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1_1 C7A_1 1.3938(18)
C1_1 C2_1 1.4074(17)
C1_1 C8_1 1.4757(18)
C2_1 C3_1 1.3841(18)
C2_1 H2A_1 0.9300
C3_1 C4_1 1.3928(19)
C3_1 H3A_1 0.9300
C4_1 C4A_1 1.3752(19)
C4_1 H4A_1 0.9300
C4A_1 C7A_1 1.3817(18)
C4A_1 O5_1 1.3892(15)
O5_1 C6_1 1.3917(17)
C6_1 O6_1 1.2029(17)
C6_1 N7_1 1.3636(18)
C7A_1 N7_1 1.3880(16)
N7_1 H7A_1 0.8600
C8_1 O8_1 1.2272(16)
C8_1 C9_1 1.4934(18)
C9_1 H9A_1 0.9600
C9_1 H9B_1 0.9600
C9_1 H9C_1 0.9600
C1_2 C7A_2 1.3927(19)
C1_2 C2_2 1.4070(18)
C1_2 C8_2 1.4775(18)
C2_2 C3_2 1.384(2)
C2_2 H2A_2 0.9300
C3_2 C4_2 1.399(2)
C3_2 H3A_2 0.9300
C4_2 C4A_2 1.3715(19)
C4_2 H4A_2 0.9300
C4A_2 O5_2 1.3871(17)
C4A_2 C7A_2 1.3883(18)
O5_2 C6_2 1.3878(16)
C6_2 O6_2 1.2087(16)
C6_2 N7_2 1.3591(17)
C7A_2 N7_2 1.3806(17)
N7_2 H7A_2 0.8600
C8_2 O8_2 1.2217(16)
C8_2 C9_2 1.5012(19)
C9_2 H9A_2 0.9600
C9_2 H9B_2 0.9600
C9_2 H9C_2 0.9600
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
N7_1 H7A_1 O8_1 0.86 2.30 2.7609(15) 113.7 .
N7_2 H7A_2 O8_2 0.86 2.32 2.7895(14) 114.3 .
N7_1 H7A_1 O6_2 0.86 2.35 3.1696(15) 160.6 3_565
N7_2 H7A_2 O8_1 0.86 1.97 2.7180(14) 144.5 3_565
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
C7A_1 C1_1 C2_1 C3_1 0.36(18)
C8_1 C1_1 C2_1 C3_1 -179.82(12)
C1_1 C2_1 C3_1 C4_1 -0.28(19)
C2_1 C3_1 C4_1 C4A_1 0.31(19)
C3_1 C4_1 C4A_1 C7A_1 -0.48(19)
C3_1 C4_1 C4A_1 O5_1 179.91(12)
C4_1 C4A_1 O5_1 C6_1 179.42(13)
C7A_1 C4A_1 O5_1 C6_1 -0.24(14)
C4A_1 O5_1 C6_1 O6_1 -179.74(13)
C4A_1 O5_1 C6_1 N7_1 -0.14(14)
C4_1 C4A_1 C7A_1 N7_1 -179.17(12)
O5_1 C4A_1 C7A_1 N7_1 0.51(14)
C4_1 C4A_1 C7A_1 C1_1 0.6(2)
O5_1 C4A_1 C7A_1 C1_1 -179.73(11)
C2_1 C1_1 C7A_1 C4A_1 -0.51(18)
C8_1 C1_1 C7A_1 C4A_1 179.66(12)
C2_1 C1_1 C7A_1 N7_1 179.18(13)
C8_1 C1_1 C7A_1 N7_1 -0.6(2)
O6_1 C6_1 N7_1 C7A_1 -179.98(14)
O5_1 C6_1 N7_1 C7A_1 0.46(14)
C4A_1 C7A_1 N7_1 C6_1 -0.60(14)
C1_1 C7A_1 N7_1 C6_1 179.67(13)
C7A_1 C1_1 C8_1 O8_1 1.81(18)
C2_1 C1_1 C8_1 O8_1 -178.01(12)
C7A_1 C1_1 C8_1 C9_1 -176.68(12)
C2_1 C1_1 C8_1 C9_1 3.50(19)
C7A_2 C1_2 C2_2 C3_2 0.77(19)
C8_2 C1_2 C2_2 C3_2 -178.18(12)
C1_2 C2_2 C3_2 C4_2 -0.8(2)
C2_2 C3_2 C4_2 C4A_2 0.1(2)
C3_2 C4_2 C4A_2 O5_2 178.99(12)
C3_2 C4_2 C4A_2 C7A_2 0.70(19)
C4_2 C4A_2 O5_2 C6_2 -178.03(13)
C7A_2 C4A_2 O5_2 C6_2 0.46(13)
C4A_2 O5_2 C6_2 O6_2 179.54(12)
C4A_2 O5_2 C6_2 N7_2 -0.57(13)
C4_2 C4A_2 C7A_2 N7_2 178.41(12)
O5_2 C4A_2 C7A_2 N7_2 -0.17(14)
C4_2 C4A_2 C7A_2 C1_2 -0.8(2)
O5_2 C4A_2 C7A_2 C1_2 -179.34(11)
C2_2 C1_2 C7A_2 N7_2 -178.91(13)
C8_2 C1_2 C7A_2 N7_2 0.1(2)
C2_2 C1_2 C7A_2 C4A_2 0.00(18)
C8_2 C1_2 C7A_2 C4A_2 179.00(11)
O6_2 C6_2 N7_2 C7A_2 -179.64(13)
O5_2 C6_2 N7_2 C7A_2 0.48(14)
C4A_2 C7A_2 N7_2 C6_2 -0.20(14)
C1_2 C7A_2 N7_2 C6_2 178.84(13)
C7A_2 C1_2 C8_2 O8_2 -1.47(19)
C2_2 C1_2 C8_2 O8_2 177.44(13)
C7A_2 C1_2 C8_2 C9_2 178.83(12)
C2_2 C1_2 C8_2 C9_2 -2.26(19)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 8165361 ChemSpider
