#------------------------------------------------------------------------------
#$Date: 2016-03-21 16:53:48 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178759 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/13/4101392.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_4101392
loop_
_publ_author_name
'Pastine, Stefan J'
'Gribkov, Denis V'
'Sames, Dalibor'
_publ_section_title
;
 sp3 C-H bond arylation directed by amidine protecting group:
 alpha-arylation of pyrrolidines and piperidines.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14220
_journal_page_last               14221
_journal_paper_doi               10.1021/ja064481j
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C20 H22 N2'
_chemical_formula_weight         290.40
_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                 99.4000(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8809(3)
_cell_length_b                   16.6533(10)
_cell_length_c                   16.5795(10)
_cell_measurement_reflns_used    4235
_cell_measurement_temperature    243(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.45
_cell_volume                     1601.93(16)
_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      243(2)
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.915
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11204
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9791
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.004(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0418
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1543
_reflns_number_gt                2500
_reflns_number_total             3675
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja064481jsi20060627_014847.cif
_cod_data_source_block           spnps10
_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 2.4.1 from
2010-06-29.

'_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4101392
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
N1 N 0.19372(19) 0.35814(6) 0.18786(7) 0.0424(3) Uani 1 1 d .
N2 N 0.0717(2) 0.31928(8) 0.30755(7) 0.0523(3) Uani 1 1 d .
C1 C 0.3359(3) 0.40694(9) 0.14214(9) 0.0493(4) Uani 1 1 d .
H1A H 0.4996 0.3913 0.1578 0.059 Uiso 1 1 calc R
C2 C 0.2493(4) 0.38014(11) 0.05426(11) 0.0797(7) Uani 1 1 d .
H2B H 0.2649 0.4234 0.0155 0.096 Uiso 1 1 calc R
H2C H 0.3344 0.3330 0.0401 0.096 Uiso 1 1 calc R
C3 C -0.0012(4) 0.36000(11) 0.05419(10) 0.0746(6) Uani 1 1 d .
H3A H -0.0617 0.3251 0.0081 0.090 Uiso 1 1 calc R
H3B H -0.0956 0.4087 0.0517 0.090 Uiso 1 1 calc R
C4 C 0.0057(2) 0.31651(9) 0.13568(9) 0.0456(4) Uani 1 1 d .
H4A H -0.1405 0.3259 0.1565 0.055 Uiso 1 1 calc R
C5 C 0.2185(2) 0.35444(8) 0.27080(8) 0.0397(3) Uani 1 1 d .
C6 C 0.4223(3) 0.39163(11) 0.32426(10) 0.0597(4) Uani 1 1 d .
H6A H 0.4205 0.4503 0.3195 0.072 Uiso 1 1 calc R
H6B H 0.5680 0.3709 0.3111 0.072 Uiso 1 1 calc R
C7 C 0.3849(4) 0.36502(13) 0.40825(12) 0.0831(6) Uani 1 1 d .
H7A H 0.3893 0.4111 0.4452 0.100 Uiso 1 1 calc R
H7B H 0.5039 0.3266 0.4316 0.100 Uiso 1 1 calc R
C8 C 0.1493(4) 0.32604(11) 0.39556(10) 0.0707(5) Uani 1 1 d .
H8A H 0.1581 0.2727 0.4209 0.085 Uiso 1 1 calc R
H8B H 0.0410 0.3589 0.4204 0.085 Uiso 1 1 calc R
C10 C 0.3121(2) 0.49697(8) 0.15339(8) 0.0410(3) Uani 1 1 d .
C11 C 0.4783(2) 0.54736(9) 0.13080(10) 0.0506(4) Uani 1 1 d .
H11A H 0.6040 0.5251 0.1101 0.061 Uiso 1 1 calc R
C12 C 0.4626(3) 0.62967(9) 0.13808(10) 0.0565(4) Uani 1 1 d .
H12A H 0.5770 0.6629 0.1224 0.068 Uiso 1 1 calc R
C13 C 0.2800(3) 0.66307(9) 0.16821(9) 0.0525(4) Uani 1 1 d .
H13A H 0.2690 0.7191 0.1731 0.063 Uiso 1 1 calc R
C14 C 0.1137(2) 0.61425(10) 0.19107(9) 0.0504(4) Uani 1 1 d .
H14A H -0.0111 0.6370 0.2119 0.060 Uiso 1 1 calc R
C15 C 0.1288(2) 0.53139(9) 0.18368(9) 0.0456(4) Uani 1 1 d .
H15A H 0.0137 0.4984 0.1993 0.055 Uiso 1 1 calc R
C20 C 0.0453(2) 0.22713(8) 0.12888(8) 0.0397(3) Uani 1 1 d .
C21 C 0.2583(2) 0.19167(9) 0.15465(9) 0.0451(4) Uani 1 1 d .
H21A H 0.3830 0.2237 0.1784 0.054 Uiso 1 1 calc R
C22 C 0.2905(2) 0.11014(10) 0.14600(10) 0.0540(4) Uani 1 1 d .
H22A H 0.4357 0.0872 0.1644 0.065 Uiso 1 1 calc R
C23 C 0.1104(3) 0.06250(10) 0.11053(10) 0.0588(4) Uani 1 1 d .
H23A H 0.1324 0.0071 0.1040 0.071 Uiso 1 1 calc R
C24 C -0.1024(3) 0.09670(11) 0.08467(10) 0.0583(4) Uani 1 1 d .
H24A H -0.2262 0.0645 0.0605 0.070 Uiso 1 1 calc R
C25 C -0.1344(2) 0.17772(10) 0.09407(9) 0.0514(4) Uani 1 1 d .
H25A H -0.2809 0.2001 0.0766 0.062 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 N1 C4 121.48(11)
C5 N1 C1 124.96(12)
C4 N1 C1 113.42(11)
C5 N2 C8 108.43(13)
N1 C1 C10 114.34(11)
N1 C1 C2 101.64(13)
C10 C1 C2 112.44(12)
C3 C2 C1 103.80(13)
C2 C3 C4 102.68(14)
N1 C4 C20 113.55(11)
N1 C4 C3 101.93(13)
C20 C4 C3 112.49(12)
N2 C5 N1 122.28(12)
N2 C5 C6 116.35(13)
N1 C5 C6 121.37(12)
C5 C6 C7 101.55(14)
C6 C7 C8 105.40(15)
N2 C8 C7 107.55(14)
C11 C10 C15 118.19(13)
C11 C10 C1 118.75(12)
C15 C10 C1 123.04(12)
C12 C11 C10 121.17(13)
C13 C12 C11 120.08(14)
C14 C13 C12 119.69(14)
C13 C14 C15 120.39(13)
C10 C15 C14 120.48(13)
C21 C20 C25 117.60(13)
C21 C20 C4 122.53(12)
C25 C20 C4 119.85(12)
C22 C21 C20 121.22(13)
C23 C22 C21 120.15(13)
C22 C23 C24 119.41(15)
C25 C24 C23 120.30(14)
C24 C25 C20 121.31(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.3603(18)
N1 C4 1.4626(18)
N1 C1 1.4634(17)
N2 C5 1.2771(17)
N2 C8 1.460(2)
C1 C10 1.520(2)
C1 C2 1.529(2)
C2 C3 1.511(3)
C3 C4 1.528(2)
C4 C20 1.5136(19)
C5 C6 1.5032(19)
C6 C7 1.511(3)
C7 C8 1.514(3)
C10 C11 1.3856(19)
C10 C15 1.3856(18)
C11 C12 1.380(2)
C12 C13 1.374(2)
C13 C14 1.372(2)
C14 C15 1.390(2)
C20 C21 1.3875(18)
C20 C25 1.3886(19)
C21 C22 1.382(2)
C22 C23 1.376(2)
C23 C24 1.378(2)
C24 C25 1.375(2)
