#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:02:42 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180285 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/71/7117100.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_7117100
loop_
_publ_author_name
'Alejandra Millan-Ortiz'
'German Lopez-Valdez'
'Fernando Cortez-Guzman'
'Luis D. Miranda'
_publ_section_title
;
 A novel carbamoyl radical based dearomatizing spiroacylation process
;
_journal_name_full               Chem.Commun.
_journal_page_first              8345
_journal_paper_doi               10.1039/C4cc06192F
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C15 H21 N O4'
_chemical_formula_sum            'C15 H21 N O4'
_chemical_formula_weight         279.33
_chemical_melting_point          195.0(10)
_chemical_name_systematic
2-(tert-butyl)-6,9-dimethoxy-2-azaspiro[4.5]deca-6,9-diene-1,8-dione
_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_block_doi                 10.5517/cc1355s7
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-08-04 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9624(5)
_cell_length_b                   11.2771(5)
_cell_length_c                   12.2022(6)
_cell_measurement_reflns_used    4177
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.46
_cell_volume                     1508.49(12)
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'Bruker Smart Apex CCD diffractometer 01-670-01'
_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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10619
_diffrn_reflns_theta_full        27.83
_diffrn_reflns_theta_max         27.83
_diffrn_reflns_theta_min         2.46
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.489
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.244
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0408
_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)+(0.0505P)²+0.1777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                1739
_reflns_number_total             2048
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc06192f2.cif
_cod_data_source_block           205MGL13
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '194-196' was changed to '195.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 
;
_cod_database_code               7117100
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.08328(14) -0.00756(14) 0.59021(12) 0.0486(4) Uani 1 1 d . . .
O2 O 1.06099(15) 0.27226(15) 0.64610(13) 0.0544(4) Uani 1 1 d . . .
O3 O 0.70454(17) 0.1140(2) 0.80652(14) 0.0723(6) Uani 1 1 d . . .
O4 O 0.64055(14) 0.00359(15) 0.62551(13) 0.0538(4) Uani 1 1 d . . .
C1 C 1.04246(18) 0.05858(18) 0.52017(15) 0.0345(4) Uani 1 1 d . . .
N2 N 1.07510(15) 0.06518(15) 0.41407(13) 0.0364(4) Uani 1 1 d . . .
C3 C 1.0016(2) 0.1501(2) 0.35191(16) 0.0438(5) Uani 1 1 d . . .
H3A H 0.9387 0.1099 0.3101 0.053 Uiso 1 1 calc R . .
H3B H 1.0520 0.1959 0.3022 0.053 Uiso 1 1 calc R . .
C4 C 0.9459(2) 0.22865(19) 0.43938(17) 0.0462(5) Uani 1 1 d . . .
H4A H 0.8659 0.2566 0.4172 0.055 Uiso 1 1 calc R . .
H4B H 0.9977 0.2965 0.4542 0.055 Uiso 1 1 calc R . .
C5 C 0.93676(18) 0.14747(17) 0.54072(15) 0.0355(4) Uani 1 1 d . . .
C6 C 0.9565(2) 0.20926(18) 0.64783(17) 0.0402(5) Uani 1 1 d . . .
C7 C 0.8801(2) 0.1997(2) 0.73270(18) 0.0456(5) Uani 1 1 d . . .
H7 H 0.8971 0.2412 0.7968 0.055 Uiso 1 1 calc R . .
C8 C 0.7718(2) 0.1268(2) 0.72789(17) 0.0457(5) Uani 1 1 d . . .
C9 C 0.74625(18) 0.0668(2) 0.62199(17) 0.0398(5) Uani 1 1 d . . .
C10 C 0.82138(19) 0.07680(19) 0.53720(17) 0.0384(4) Uani 1 1 d . . .
H10 H 0.8013 0.0379 0.4724 0.046 Uiso 1 1 calc R . .
C11 C 1.15918(19) -0.0223(2) 0.36202(18) 0.0433(5) Uani 1 1 d . . .
C12 C 1.2851(2) -0.0087(3) 0.4135(2) 0.0667(8) Uani 1 1 d . . .
H12A H 1.2825 -0.0353 0.4882 0.100 Uiso 1 1 calc R . .
H12B H 1.3091 0.0731 0.4114 0.100 Uiso 1 1 calc R . .
H12C H 1.3430 -0.0554 0.3733 0.100 Uiso 1 1 calc R . .
C13 C 1.1079(3) -0.1459(2) 0.3781(3) 0.0692(8) Uani 1 1 d . . .
H13A H 1.0267 -0.1494 0.3489 0.104 Uiso 1 1 calc R . .
H13B H 1.1060 -0.1643 0.4549 0.104 Uiso 1 1 calc R . .
H13C H 1.1586 -0.2023 0.3408 0.104 Uiso 1 1 calc R . .
C14 C 1.1686(3) 0.0034(3) 0.2396(2) 0.0718(8) Uani 1 1 d . . .
H14A H 1.0900 -0.0065 0.2062 0.108 Uiso 1 1 calc R . .
H14B H 1.2257 -0.0504 0.2067 0.108 Uiso 1 1 calc R . .
H14C H 1.1960 0.0835 0.2289 0.108 Uiso 1 1 calc R . .
C15 C 1.0956(3) 0.3342(2) 0.7434(2) 0.0607(7) Uani 1 1 d . . .
H15A H 1.1720 0.3738 0.7315 0.091 Uiso 1 1 calc R . .
H15B H 1.1039 0.2789 0.8027 0.091 Uiso 1 1 calc R . .
H15C H 1.0342 0.3917 0.7614 0.091 Uiso 1 1 calc R . .
C16 C 0.6060(2) -0.0536(3) 0.5267(2) 0.0595(6) Uani 1 1 d . . .
H16A H 0.5318 -0.0970 0.5382 0.089 Uiso 1 1 calc R . .
H16B H 0.6694 -0.1073 0.5044 0.089 Uiso 1 1 calc R . .
H16C H 0.5935 0.0047 0.4705 0.089 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 O2 C15 118.06(18) . .
C9 O4 C16 116.01(17) . .
O1 C1 N2 127.64(19) . .
O1 C1 C5 123.75(17) . .
N2 C1 C5 108.56(16) . .
C1 N2 C3 112.86(17) . .
C1 N2 C11 122.52(18) . .
C3 N2 C11 123.52(16) . .
N2 C3 C4 103.85(16) . .
C3 C4 C5 104.11(16) . .
C10 C5 C6 113.30(17) . .
C10 C5 C4 110.39(17) . .
C6 C5 C4 114.48(16) . .
C10 C5 C1 106.41(15) . .
C6 C5 C1 109.48(16) . .
C4 C5 C1 101.84(16) . .
C7 C6 O2 126.0(2) . .
C7 C6 C5 123.2(2) . .
O2 C6 C5 110.78(17) . .
C6 C7 C8 122.0(2) . .
O3 C8 C7 122.2(2) . .
O3 C8 C9 121.1(2) . .
C7 C8 C9 116.69(19) . .
C10 C9 O4 126.7(2) . .
C10 C9 C8 121.5(2) . .
O4 C9 C8 111.82(18) . .
C9 C10 C5 123.2(2) . .
N2 C11 C13 108.89(18) . .
N2 C11 C12 108.53(18) . .
C13 C11 C12 112.0(2) . .
N2 C11 C14 109.5(2) . .
C13 C11 C14 109.1(2) . .
C12 C11 C14 108.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.220(2) .
O2 C6 1.348(3) .
O2 C15 1.429(3) .
O3 C8 1.219(3) .
O4 C9 1.361(3) .
O4 C16 1.419(3) .
C1 N2 1.345(2) .
C1 C5 1.552(3) .
N2 C3 1.463(3) .
N2 C11 1.492(3) .
C3 C4 1.515(3) .
C4 C5 1.542(3) .
C5 C10 1.496(3) .
C5 C6 1.497(3) .
C6 C7 1.336(3) .
C7 C8 1.445(3) .
C8 C9 1.485(3) .
C9 C10 1.327(3) .
C11 C13 1.516(3) .
C11 C12 1.525(3) .
C11 C14 1.525(3) .
