#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/22/1512234.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_1512234
loop_
_publ_author_name
'Ramirez, Thomas A.'
'Wang, Qian'
'Zhu, Yingguang'
'Zheng, Huaiji'
'Peng, Xingao'
'Cornwall, Richard G.'
'Shi, Yian'
_publ_section_title
;
 Pd(0)-Catalyzed Sequential C-N Bond Formation via Allylic and Aromatic
 C-H Amination of α-Methylstyrenes with Diaziridinone.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4210
_journal_page_last               4213
_journal_paper_doi               10.1021/ol401935c
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C23 H37 N3 O2'
_chemical_formula_sum            'C23 H37 N3 O2'
_chemical_formula_weight         387.56
_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                 111.678(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8005(10)
_cell_length_b                   18.9134(18)
_cell_length_c                   11.8008(11)
_cell_measurement_reflns_used    9738
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      33.57
_cell_measurement_theta_min      2.29
_cell_volume                     2240.1(4)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2009)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            64302
_diffrn_reflns_theta_full        33.72
_diffrn_reflns_theta_max         33.72
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE (Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         8798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0642P)²+0.4592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1257
_reflns_number_gt                6823
_reflns_number_total             8798
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401935c_si_002.cif
_cod_data_source_block           shi05_p21c
_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.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

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      'P 21/c'
_cod_database_code               1512234
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
O1 O -0.21178(6) 0.55926(4) 0.08081(6) 0.02308(14) Uani 1 1 d .
O2 O 0.23823(7) 0.67908(4) 0.65975(6) 0.02214(14) Uani 1 1 d .
N1 N -0.06565(7) 0.64815(4) 0.07577(6) 0.01631(13) Uani 1 1 d .
N2 N 0.00894(7) 0.56143(4) 0.21577(6) 0.01526(13) Uani 1 1 d .
N3 N 0.35580(7) 0.60702(4) 0.25301(6) 0.01529(13) Uani 1 1 d .
C1 C -0.10094(8) 0.58675(4) 0.12047(7) 0.01596(14) Uani 1 1 d .
C2 C 0.05836(8) 0.67382(5) 0.16722(8) 0.01815(15) Uani 1 1 d .
H2A H 0.0407 0.7068 0.2246 0.022 Uiso 1 1 calc R
H2B H 0.1140 0.6980 0.1285 0.022 Uiso 1 1 calc R
C3 C 0.12607(7) 0.60585(4) 0.23259(7) 0.01461(14) Uani 1 1 d .
C4 C 0.22514(8) 0.57676(5) 0.17707(8) 0.01858(15) Uani 1 1 d .
H4A H 0.2280 0.5245 0.1804 0.022 Uiso 1 1 calc R
H4B H 0.1993 0.5919 0.0911 0.022 Uiso 1 1 calc R
C5 C 0.21706(8) 0.62316(4) 0.36070(7) 0.01409(14) Uani 1 1 d .
C6 C 0.34998(8) 0.62226(4) 0.36787(7) 0.01396(13) Uani 1 1 d .
C7 C 0.44935(8) 0.63963(5) 0.47938(8) 0.01764(15) Uani 1 1 d .
H7 H 0.5404 0.6381 0.4882 0.021 Uiso 1 1 calc R
C8 C 0.41474(8) 0.65936(5) 0.57806(8) 0.01822(15) Uani 1 1 d .
H8 H 0.4829 0.6717 0.6534 0.022 Uiso 1 1 calc R
C9 C 0.28198(8) 0.66126(4) 0.56775(7) 0.01631(14) Uani 1 1 d .
C10 C 0.18184(8) 0.64277(4) 0.45711(7) 0.01623(14) Uani 1 1 d .
H10 H 0.0909 0.6437 0.4485 0.019 Uiso 1 1 calc R
C11 C -0.16903(8) 0.69979(5) 0.00489(8) 0.01878(15) Uani 1 1 d .
C12 C -0.09667(9) 0.76074(5) -0.02945(9) 0.02604(19) Uani 1 1 d .
H12A H -0.0413 0.7421 -0.0722 0.039 Uiso 1 1 calc R
H12B H -0.0401 0.7854 0.0447 0.039 Uiso 1 1 calc R
H12C H -0.1622 0.7939 -0.0828 0.039 Uiso 1 1 calc R
C13 C -0.26427(10) 0.66597(6) -0.11282(9) 0.0293(2) Uani 1 1 d .
H13A H -0.2131 0.6467 -0.1591 0.044 Uiso 1 1 calc R
H13B H -0.3266 0.7018 -0.1620 0.044 Uiso 1 1 calc R
H13C H -0.3141 0.6278 -0.0927 0.044 Uiso 1 1 calc R
C14 C -0.24669(11) 0.72716(6) 0.08101(11) 0.0312(2) Uani 1 1 d .
H14A H -0.3119 0.7624 0.0339 0.047 Uiso 1 1 calc R
H14B H -0.1849 0.7489 0.1559 0.047 Uiso 1 1 calc R
H14C H -0.2931 0.6877 0.1020 0.047 Uiso 1 1 calc R
C15 C 0.00569(8) 0.48957(4) 0.26702(7) 0.01698(15) Uani 1 1 d .
C16 C -0.03289(11) 0.43441(5) 0.16515(9) 0.0313(2) Uani 1 1 d .
H16A H -0.1239 0.4435 0.1080 0.047 Uiso 1 1 calc R
H16B H -0.0283 0.3871 0.2003 0.047 Uiso 1 1 calc R
H16C H 0.0288 0.4372 0.1218 0.047 Uiso 1 1 calc R
C17 C -0.09789(10) 0.49036(6) 0.32737(10) 0.02693(19) Uani 1 1 d .
H17A H -0.0740 0.5267 0.3911 0.040 Uiso 1 1 calc R
H17B H -0.1000 0.4440 0.3637 0.040 Uiso 1 1 calc R
H17C H -0.1859 0.5009 0.2659 0.040 Uiso 1 1 calc R
C18 C 0.14094(9) 0.46891(5) 0.36388(8) 0.02196(17) Uani 1 1 d .
H18A H 0.2091 0.4694 0.3275 0.033 Uiso 1 1 calc R
H18B H 0.1349 0.4214 0.3945 0.033 Uiso 1 1 calc R
H18C H 0.1651 0.5028 0.4315 0.033 Uiso 1 1 calc R
C19 C 0.47603(8) 0.57658(5) 0.23762(8) 0.01759(15) Uani 1 1 d .
C20 C 0.59206(9) 0.62890(6) 0.28208(10) 0.0271(2) Uani 1 1 d .
H20A H 0.5616 0.6756 0.2468 0.041 Uiso 1 1 calc R
H20B H 0.6640 0.6126 0.2567 0.041 Uiso 1 1 calc R
H20C H 0.6250 0.6320 0.3712 0.041 Uiso 1 1 calc R
C21 C 0.44434(10) 0.56485(6) 0.10172(9) 0.0289(2) Uani 1 1 d .
H21A H 0.3762 0.5280 0.0714 0.043 Uiso 1 1 calc R
H21B H 0.5253 0.5500 0.0892 0.043 Uiso 1 1 calc R
H21C H 0.4112 0.6090 0.0573 0.043 Uiso 1 1 calc R
C22 C 0.51579(10) 0.50663(6) 0.30644(11) 0.0295(2) Uani 1 1 d .
H22A H 0.5354 0.5146 0.3934 0.044 Uiso 1 1 calc R
H22B H 0.5951 0.4877 0.2954 0.044 Uiso 1 1 calc R
H22C H 0.4424 0.4728 0.2746 0.044 Uiso 1 1 calc R
C23 C 0.33748(11) 0.69426(6) 0.77619(8) 0.0273(2) Uani 1 1 d .
H23A H 0.3956 0.6530 0.8053 0.041 Uiso 1 1 calc R
H23B H 0.2945 0.7053 0.8340 0.041 Uiso 1 1 calc R
H23C H 0.3907 0.7349 0.7693 0.041 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
C9 O2 C23 117.04(7)
C1 N1 C2 107.69(6)
C1 N1 C11 120.63(7)
C2 N1 C11 119.43(7)
C1 N2 C3 110.42(7)
C1 N2 C15 120.16(7)
C3 N2 C15 127.83(6)
C6 N3 C4 106.87(6)
C6 N3 C19 123.09(7)
C4 N3 C19 117.10(7)
O1 C1 N2 125.85(8)
O1 C1 N1 125.17(8)
N2 C1 N1 108.98(7)
N1 C2 C3 103.26(7)
N2 C3 C5 118.08(7)
N2 C3 C2 100.60(6)
C5 C3 C2 109.59(7)
N2 C3 C4 115.78(7)
C5 C3 C4 101.87(6)
C2 C3 C4 111.08(7)
N3 C4 C3 105.07(6)
C10 C5 C6 122.74(7)
C10 C5 C3 127.72(7)
C6 C5 C3 109.35(7)
C7 C6 C5 117.78(7)
C7 C6 N3 131.52(7)
C5 C6 N3 110.59(7)
C6 C7 C8 119.93(8)
C9 C8 C7 121.11(7)
O2 C9 C8 125.39(7)
O2 C9 C10 115.18(7)
C8 C9 C10 119.42(7)
C5 C10 C9 118.98(7)
N1 C11 C14 110.68(7)
N1 C11 C12 107.05(7)
C14 C11 C12 110.22(8)
N1 C11 C13 110.46(8)
C14 C11 C13 110.14(8)
C12 C11 C13 108.22(8)
N2 C15 C16 110.06(7)
N2 C15 C17 108.04(7)
C16 C15 C17 109.78(8)
N2 C15 C18 112.01(7)
C16 C15 C18 108.65(7)
C17 C15 C18 108.27(7)
N3 C19 C21 108.45(7)
N3 C19 C22 110.84(7)
C21 C19 C22 110.00(8)
N3 C19 C20 110.39(7)
C21 C19 C20 106.95(8)
C22 C19 C20 110.12(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2282(10)
O2 C9 1.3764(10)
O2 C23 1.4252(11)
N1 C1 1.3860(11)
N1 C2 1.4582(11)
N1 C11 1.4866(11)
N2 C1 1.3843(10)
N2 C3 1.4697(10)
N2 C15 1.4934(11)
N3 C6 1.4097(10)
N3 C4 1.4792(11)
N3 C19 1.4916(11)
C2 C3 1.5382(12)
C3 C5 1.5036(11)
C3 C4 1.5475(11)
C5 C10 1.3771(11)
C5 C6 1.4066(11)
C6 C7 1.3957(11)
C7 C8 1.3988(12)
C8 C9 1.3939(12)
C9 C10 1.3977(11)
C11 C14 1.5281(14)
C11 C12 1.5291(13)
C11 C13 1.5301(13)
C15 C16 1.5287(13)
C15 C17 1.5322(13)
C15 C18 1.5361(12)
C19 C21 1.5274(13)
C19 C22 1.5286(14)
C19 C20 1.5295(12)
