#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/58/4025817.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_4025817
loop_
_publ_author_name
'Zhengren Xu'
'Weimin Hu'
'Qiang Liu'
'Lihe Zhang'
'Yanxing Jia'
_publ_section_title
;
 Total Synthesis of Clavicipitic Acid and Aurantioclavine: Stereochemistry
 of Clavicipitic Acid Revisited
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7626
_journal_page_last               7635
_journal_paper_doi               10.1021/jo101506c
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H20 N2 O2'
_chemical_formula_sum            'C17 H20 N2 O2'
_chemical_formula_weight         284.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0258(18)
_cell_length_b                   9.687(2)
_cell_length_c                   17.717(5)
_cell_measurement_reflns_used    51
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      18.73
_cell_measurement_theta_min      2.29
_cell_volume                     1549.0(6)
_computing_cell_refinement       'XSCANS (Bruker, 1997)'
_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_data_reduction        'XSCANS (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2213
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0082(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         1662
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0010P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                1208
_reflns_number_total             1662
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101506c_si_004.cif
_cod_data_source_block           cuiyx-6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z 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_database_code               4025817
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1343(2) 0.6628(2) 0.80049(13) 0.0870(7) Uani 1 1 d . . .
O2 O -0.0146(3) 0.4711(2) 0.8197(2) 0.1457(11) Uani 1 1 d U . .
N1 N 0.1721(2) 0.53848(19) 0.69969(11) 0.0487(5) Uani 1 1 d . . .
H1B H 0.1108 0.4655 0.6965 0.070(8) Uiso 1 1 d R . .
N2 N 0.5641(2) 0.8859(2) 0.74332(13) 0.0667(7) Uani 1 1 d . . .
H2C H 0.6375 0.9396 0.7531 0.080 Uiso 1 1 calc R . .
C1 C 0.0998(3) 0.6472(3) 0.74480(15) 0.0511(6) Uani 1 1 d . . .
H1A H 0.0562 0.7163 0.7111 0.061 Uiso 1 1 calc R . .
C2 C 0.2131(3) 0.7162(3) 0.79630(15) 0.0606(8) Uani 1 1 d . . .
H2A H 0.1650 0.7917 0.8227 0.073 Uiso 1 1 calc R . .
H2B H 0.2450 0.6498 0.8339 0.073 Uiso 1 1 calc R . .
C3 C 0.3475(3) 0.7714(2) 0.75643(15) 0.0526(7) Uani 1 1 d . . .
C4 C 0.4115(3) 0.7345(2) 0.68460(13) 0.0496(6) Uani 1 1 d . . .
C5 C 0.3665(3) 0.6507(3) 0.62295(14) 0.0511(7) Uani 1 1 d . . .
C6 C 0.2148(3) 0.5832(3) 0.62200(13) 0.0501(7) Uani 1 1 d . . .
H6A H 0.1428 0.6525 0.6053 0.060 Uiso 1 1 calc R . .
C7 C 0.2033(3) 0.4616(3) 0.56991(14) 0.0576(7) Uani 1 1 d . . .
H7A H 0.2882 0.4090 0.5621 0.069 Uiso 1 1 calc R . .
C8 C 0.0806(3) 0.4235(3) 0.53406(15) 0.0595(8) Uani 1 1 d . . .
C9 C -0.0639(3) 0.4993(3) 0.53737(18) 0.0733(9) Uani 1 1 d . . .
H9A H -0.0583 0.5705 0.5749 0.110 Uiso 1 1 calc R . .
H9B H -0.1417 0.4359 0.5503 0.110 Uiso 1 1 calc R . .
H9C H -0.0844 0.5399 0.4890 0.110 Uiso 1 1 calc R . .
C10 C 0.0781(4) 0.2952(3) 0.48474(18) 0.0873(11) Uani 1 1 d . . .
H10A H 0.1741 0.2525 0.4853 0.131 Uiso 1 1 calc R . .
H10B H 0.0530 0.3206 0.4339 0.131 Uiso 1 1 calc R . .
H10C H 0.0057 0.2316 0.5038 0.131 Uiso 1 1 calc R . .
C11 C 0.4614(3) 0.6415(3) 0.56172(15) 0.0614(8) Uani 1 1 d . . .
H11A H 0.4336 0.5884 0.5203 0.074 Uiso 1 1 calc R . .
C12 C 0.5992(3) 0.7104(3) 0.56035(16) 0.0699(9) Uani 1 1 d . . .
H12A H 0.6613 0.6983 0.5190 0.084 Uiso 1 1 calc R . .
C13 C 0.6437(3) 0.7942(3) 0.61787(16) 0.0679(8) Uani 1 1 d . . .
H13A H 0.7337 0.8408 0.6162 0.081 Uiso 1 1 calc R . .
C14 C 0.5479(3) 0.8068(3) 0.67936(15) 0.0573(7) Uani 1 1 d . . .
C15 C 0.4436(3) 0.8649(3) 0.78887(16) 0.0626(8) Uani 1 1 d . . .
H15A H 0.4287 0.9076 0.8352 0.075 Uiso 1 1 calc R . .
C16 C -0.0197(3) 0.5837(3) 0.79252(18) 0.0654(8) Uani 1 1 d U . .
C17 C -0.2584(3) 0.6076(4) 0.8438(2) 0.0976(12) Uani 1 1 d . . .
H17A H -0.3333 0.6772 0.8490 0.146 Uiso 1 1 calc R . .
H17B H -0.2244 0.5800 0.8929 0.146 Uiso 1 1 calc R . .
H17C H -0.2990 0.5291 0.8180 0.146 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O1 C17 116.9(2) . . ?
C1 N1 C6 114.00(19) . . ?
C1 N1 H1B 108.9 . . ?
C6 N1 H1B 109.1 . . ?
C15 N2 C14 108.6(2) . . ?
C15 N2 H2C 125.7 . . ?
C14 N2 H2C 125.7 . . ?
N1 C1 C16 109.3(2) . . ?
N1 C1 C2 109.91(19) . . ?
C16 C1 C2 108.9(2) . . ?
N1 C1 H1A 109.6 . . ?
C16 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
C3 C2 C1 114.6(2) . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C15 C3 C4 106.2(2) . . ?
C15 C3 C2 123.1(2) . . ?
C4 C3 C2 130.5(2) . . ?
C14 C4 C5 118.7(2) . . ?
C14 C4 C3 106.4(2) . . ?
C5 C4 C3 134.9(2) . . ?
C11 C5 C4 117.5(2) . . ?
C11 C5 C6 121.5(2) . . ?
C4 C5 C6 120.9(2) . . ?
N1 C6 C7 108.8(2) . . ?
N1 C6 C5 110.3(2) . . ?
C7 C6 C5 114.1(2) . . ?
N1 C6 H6A 107.8 . . ?
C7 C6 H6A 107.8 . . ?
C5 C6 H6A 107.8 . . ?
C8 C7 C6 124.7(2) . . ?
C8 C7 H7A 117.6 . . ?
C6 C7 H7A 117.6 . . ?
C7 C8 C9 124.8(3) . . ?
C7 C8 C10 121.0(3) . . ?
C9 C8 C10 114.2(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 C12 121.9(3) . . ?
C5 C11 H11A 119.1 . . ?
C12 C11 H11A 119.1 . . ?
C13 C12 C11 121.9(3) . . ?
C13 C12 H12A 119.0 . . ?
C11 C12 H12A 119.0 . . ?
C12 C13 C14 116.9(3) . . ?
C12 C13 H13A 121.5 . . ?
C14 C13 H13A 121.5 . . ?
N2 C14 C13 128.7(3) . . ?
N2 C14 C4 108.3(2) . . ?
C13 C14 C4 123.0(2) . . ?
N2 C15 C3 110.6(2) . . ?
N2 C15 H15A 124.7 . . ?
C3 C15 H15A 124.7 . . ?
O2 C16 O1 121.9(3) . . ?
O2 C16 C1 125.0(3) . . ?
O1 C16 C1 113.1(2) . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.295(3) . ?
O1 C17 1.459(4) . ?
O2 C16 1.193(4) . ?
N1 C1 1.474(3) . ?
N1 C6 1.494(3) . ?
N1 H1B 0.9000 . ?
N2 C15 1.369(3) . ?
N2 C14 1.376(3) . ?
N2 H2C 0.8600 . ?
C1 C16 1.502(4) . ?
C1 C2 1.525(3) . ?
C1 H1A 0.9800 . ?
C2 C3 1.503(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C15 1.379(4) . ?
C3 C4 1.443(3) . ?
C4 C14 1.420(4) . ?
C4 C5 1.420(3) . ?
C5 C11 1.385(4) . ?
C5 C6 1.517(3) . ?
C6 C7 1.500(3) . ?
C6 H6A 0.9800 . ?
C7 C8 1.329(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.498(4) . ?
C8 C10 1.519(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.411(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.363(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.396(4) . ?
C13 H13A 0.9300 . ?
C15 H15A 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
N1 H1B O2 0.90 2.46 2.791(4) 102.1 .
N2 H2C N1 0.86 2.14 2.979(3) 165.7 3_656
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9294755
