#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:46:54 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180315 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/29/7152904.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_7152904
loop_
_publ_author_name
'Li, Guang'
'Zhang, Xun'
'Li, Qi'
'Feng, Pengju'
'Shi, Yian'
_publ_section_title
;
 A concise approach to the spiroiminal fragment of marineosins.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2936
_journal_page_last               2938
_journal_paper_doi               10.1039/c3ob40208h
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C14 H20 N2 O2'
_chemical_formula_sum            'C14 H20 N2 O2'
_chemical_formula_weight         248.32
_chemical_name_systematic
;
?
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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            8
_cell_length_a                   15.663(3)
_cell_length_b                   8.2891(17)
_cell_length_c                   21.056(4)
_cell_measurement_reflns_used    10122
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.62
_cell_volume                     2733.7(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9483
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9863
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.245
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0731
_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)+(0.0253P)²+1.9630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                2066
_reflns_number_total             2396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob40208h.txt
_cod_data_source_block           a4
_cod_original_cell_volume        2733.7(10)
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               7152904
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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
O1 O 0.59644(10) 0.4975(2) 0.37348(8) 0.0275(4) Uani 1 1 d .
O2 O 0.69237(13) 0.6293(2) 0.46341(9) 0.0429(6) Uani 1 1 d .
N1 N 0.56623(13) 0.7524(2) 0.32818(10) 0.0242(5) Uani 1 1 d .
N2 N 0.59898(13) 0.9061(2) 0.20759(10) 0.0267(5) Uani 1 1 d .
H2 H 0.5484 0.8601 0.2074 0.032 Uiso 1 1 calc R
C1 C 0.57509(16) 0.6610(3) 0.38838(12) 0.0257(6) Uani 1 1 d .
C2 C 0.52935(16) 0.4103(3) 0.34152(13) 0.0288(6) Uani 1 1 d .
H2A H 0.5152 0.4671 0.3010 0.035 Uiso 1 1 calc R
C3 C 0.45003(17) 0.4032(3) 0.38265(13) 0.0327(7) Uani 1 1 d .
H3B H 0.4622 0.3396 0.4214 0.039 Uiso 1 1 calc R
H3A H 0.4036 0.3485 0.3591 0.039 Uiso 1 1 calc R
C4 C 0.42148(17) 0.5722(3) 0.40125(14) 0.0352(7) Uani 1 1 d .
H4A H 0.3990 0.6288 0.3634 0.042 Uiso 1 1 calc R
H4B H 0.3749 0.5649 0.4329 0.042 Uiso 1 1 calc R
C5 C 0.49516(18) 0.6674(3) 0.42892(13) 0.0328(7) Uani 1 1 d .
H5B H 0.5086 0.6246 0.4717 0.039 Uiso 1 1 calc R
H5A H 0.4774 0.7814 0.4339 0.039 Uiso 1 1 calc R
C6 C 0.65402(17) 0.7360(3) 0.41979(13) 0.0308(7) Uani 1 1 d .
H6 H 0.6358 0.8351 0.4432 0.037 Uiso 1 1 calc R
C7 C 0.70841(16) 0.7870(3) 0.36374(13) 0.0317(7) Uani 1 1 d .
H7B H 0.7403 0.8876 0.3727 0.038 Uiso 1 1 calc R
H7A H 0.7489 0.7012 0.3510 0.038 Uiso 1 1 calc R
C8 C 0.64038(15) 0.8129(3) 0.31436(13) 0.0239(6) Uani 1 1 d .
C9 C 0.65707(15) 0.8975(3) 0.25616(13) 0.0247(6) Uani 1 1 d .
C10 C 0.72797(16) 0.9849(3) 0.23779(14) 0.0309(7) Uani 1 1 d .
H10 H 0.7787 0.9995 0.2618 0.037 Uiso 1 1 calc R
C11 C 0.71157(17) 1.0485(3) 0.17727(14) 0.0351(7) Uani 1 1 d .
H11 H 0.7486 1.1148 0.1529 0.042 Uiso 1 1 calc R
C12 C 0.63166(17) 0.9964(3) 0.16014(14) 0.0329(7) Uani 1 1 d .
H12 H 0.6038 1.0201 0.1212 0.039 Uiso 1 1 calc R
C13 C 0.56531(19) 0.2459(3) 0.32608(16) 0.0423(8) Uani 1 1 d .
H13C H 0.5835 0.1926 0.3654 0.063 Uiso 1 1 calc R
H13B H 0.6144 0.2578 0.2976 0.063 Uiso 1 1 calc R
H13A H 0.5213 0.1805 0.3052 0.063 Uiso 1 1 calc R
C14 C 0.7541(2) 0.7080(4) 0.50177(17) 0.0609(11) Uani 1 1 d .
H14C H 0.7785 0.6306 0.5319 0.091 Uiso 1 1 calc R
H14A H 0.7269 0.7963 0.5252 0.091 Uiso 1 1 calc R
H14B H 0.7996 0.7514 0.4747 0.091 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
C1 O1 C2 114.02(18)
C6 O2 C14 111.9(2)
C8 N1 C1 107.8(2)
C12 N2 C9 109.2(2)
C12 N2 H2 125.4
C9 N2 H2 125.4
O1 C1 N1 108.6(2)
O1 C1 C5 110.5(2)
N1 C1 C5 112.7(2)
O1 C1 C6 106.8(2)
N1 C1 C6 103.7(2)
C5 C1 C6 114.1(2)
O1 C2 C13 106.3(2)
O1 C2 C3 110.5(2)
C13 C2 C3 113.2(2)
O1 C2 H2A 108.9
C13 C2 H2A 108.9
C3 C2 H2A 108.9
C2 C3 C4 110.6(2)
C2 C3 H3B 109.5
C4 C3 H3B 109.5
C2 C3 H3A 109.5
C4 C3 H3A 109.5
H3B C3 H3A 108.1
C5 C4 C3 110.8(2)
C5 C4 H4A 109.5
C3 C4 H4A 109.5
C5 C4 H4B 109.5
C3 C4 H4B 109.5
H4A C4 H4B 108.1
C4 C5 C1 113.2(2)
C4 C5 H5B 108.9
C1 C5 H5B 108.9
C4 C5 H5A 108.9
C1 C5 H5A 108.9
H5B C5 H5A 107.7
O2 C6 C7 116.3(2)
O2 C6 C1 111.7(2)
C7 C6 C1 103.3(2)
O2 C6 H6 108.4
C7 C6 H6 108.4
C1 C6 H6 108.4
C8 C7 C6 100.4(2)
C8 C7 H7B 111.7
C6 C7 H7B 111.7
C8 C7 H7A 111.7
C6 C7 H7A 111.7
H7B C7 H7A 109.5
N1 C8 C9 122.9(2)
N1 C8 C7 115.1(2)
C9 C8 C7 122.0(2)
N2 C9 C10 107.3(2)
N2 C9 C8 122.8(2)
C10 C9 C8 129.9(2)
C9 C10 C11 107.7(2)
C9 C10 H10 126.1
C11 C10 H10 126.1
C12 C11 C10 106.7(2)
C12 C11 H11 126.6
C10 C11 H11 126.6
N2 C12 C11 109.0(3)
N2 C12 H12 125.5
C11 C12 H12 125.5
C2 C13 H13C 109.5
C2 C13 H13B 109.5
H13C C13 H13B 109.5
C2 C13 H13A 109.5
H13C C13 H13A 109.5
H13B C13 H13A 109.5
O2 C14 H14C 109.5
O2 C14 H14A 109.5
H14C C14 H14A 109.5
O2 C14 H14B 109.5
H14C C14 H14B 109.5
H14A C14 H14B 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.431(3)
O1 C2 1.442(3)
O2 C6 1.410(3)
O2 C14 1.419(3)
N1 C8 1.298(3)
N1 C1 1.483(3)
N2 C12 1.349(3)
N2 C9 1.371(3)
N2 H2 0.8800
C1 C5 1.516(4)
C1 C6 1.534(3)
C2 C13 1.510(4)
C2 C3 1.515(4)
C2 H2A 1.0000
C3 C4 1.522(4)
C3 H3B 0.9900
C3 H3A 0.9900
C4 C5 1.515(4)
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5B 0.9900
C5 H5A 0.9900
C6 C7 1.516(4)
C6 H6 1.0000
C7 C8 1.504(3)
C7 H7B 0.9900
C7 H7A 0.9900
C8 C9 1.436(4)
C9 C10 1.381(3)
C10 C11 1.403(4)
C10 H10 0.9500
C11 C12 1.372(4)
C11 H11 0.9500
C12 H12 0.9500
C13 H13C 0.9800
C13 H13B 0.9800
C13 H13A 0.9800
C14 H14C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
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
N2 H2 N1 0.88 2.71 2.887(3) 92.6
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
C2 O1 C1 N1 -66.9(2)
C2 O1 C1 C5 57.2(3)
C2 O1 C1 C6 -178.1(2)
C8 N1 C1 O1 -90.7(2)
C8 N1 C1 C5 146.6(2)
C8 N1 C1 C6 22.7(3)
C1 O1 C2 C13 176.4(2)
C1 O1 C2 C3 -60.4(3)
O1 C2 C3 C4 55.9(3)
C13 C2 C3 C4 175.1(2)
C2 C3 C4 C5 -51.0(3)
C3 C4 C5 C1 49.4(3)
O1 C1 C5 C4 -51.3(3)
N1 C1 C5 C4 70.3(3)
C6 C1 C5 C4 -171.7(2)
C14 O2 C6 C7 73.7(3)
C14 O2 C6 C1 -168.0(3)
O1 C1 C6 O2 -42.2(3)
N1 C1 C6 O2 -156.8(2)
C5 C1 C6 O2 80.2(3)
O1 C1 C6 C7 83.6(2)
N1 C1 C6 C7 -31.0(2)
C5 C1 C6 C7 -154.0(2)
O2 C6 C7 C8 149.8(2)
C1 C6 C7 C8 27.0(2)
C1 N1 C8 C9 174.5(2)
C1 N1 C8 C7 -5.1(3)
C6 C7 C8 N1 -14.8(3)
C6 C7 C8 C9 165.6(2)
C12 N2 C9 C10 -0.2(3)
C12 N2 C9 C8 178.5(2)
N1 C8 C9 N2 -7.3(4)
C7 C8 C9 N2 172.3(2)
N1 C8 C9 C10 171.1(3)
C7 C8 C9 C10 -9.4(4)
N2 C9 C10 C11 0.6(3)
C8 C9 C10 C11 -178.0(2)
C9 C10 C11 C12 -0.7(3)
C9 N2 C12 C11 -0.2(3)
C10 C11 C12 N2 0.6(3)
