#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/21/7102175.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_7102175
loop_
_publ_author_name
'Davies, Stephen G'
'Ling, Kenneth B'
'Roberts, Paul M'
'Russell, Angela J'
'Thomson, James E'
_publ_section_title
;
 Diastereoselective Simmons-Smith cyclopropanations of allylic amines
 and carbamates.
;
_journal_issue                   39
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4029
_journal_page_last               4031
_journal_paper_doi               10.1039/b711358g
_journal_year                    2007
_chemical_formula_moiety         'C15 H15 N1 O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.29
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             06-03-10
_audit_creation_method           CRYSTALS_ver_12.82
_cell_angle_alpha                90
_cell_angle_beta                 109.9188(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5766(3)
_cell_length_b                   7.0349(3)
_cell_length_c                   10.6494(5)
_cell_measurement_reflns_used    1433
_cell_measurement_temperature    190
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     604.10(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT. Nonius (1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      190
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2708
_diffrn_reflns_theta_full        26.911
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_min         5.304
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0452
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1468
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.1044
_refine_ls_shift/su_max          0.007654
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(F²) + ( 0.04P)² + 1.06P]
where P=(max(Fo²,0) + 2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2144
_refine_ls_wR_factor_gt          0.2057
_refine_ls_wR_factor_ref         0.2144
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1206
_reflns_number_total             1468
_reflns_threshold_expression     I>2.00u(I)
_cod_data_source_file            b711358g.txt
_cod_data_source_block           CRYSTALS_cif
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_original_formula_sum        'C15 H15 N1 O2'
_cod_database_code               7102175
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z
x,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1574(4) 0.2500 0.3577(3) 0.0544 1.0000 Uani S T . .
C1 C 0.2856(5) 0.2500 0.3046(4) 0.0461 1.0000 Uani S T . .
C2 C 0.4429(4) 0.2500 0.4211(4) 0.0373 1.0000 Uani S T . .
C3 C 0.6059(5) 0.2500 0.4278(5) 0.0516 1.0000 Uani S T . .
C4 C 0.7271(5) 0.2500 0.5535(5) 0.0569 1.0000 Uani S T . .
C5 C 0.6859(5) 0.2500 0.6676(5) 0.0562 1.0000 Uani S T . .
C6 C 0.5213(5) 0.2500 0.6609(4) 0.0572 1.0000 Uani S T . .
C7 C 0.4016(4) 0.2500 0.5356(4) 0.0420 1.0000 Uani S T . .
C8 C 0.2189(5) 0.2500 0.4960(4) 0.0576 1.0000 Uani S T . .
O1 O 0.2702(4) 0.2500 0.1882(3) 0.0701 1.0000 Uani S T . .
O2 O 0.1353(4) 0.2500 0.5676(3) 0.0883 1.0000 Uani S T . .
C9 C -0.0236(6) 0.2063(10) 0.2855(5) 0.0467 0.5000 Uani . U 1 -1
C10 C -0.1019(8) 0.3973(13) 0.2540(9) 0.0651 0.5000 Uani . U 1 -1
C11 C -0.2549(19) 0.455(2) 0.1398(13) 0.0776 0.5000 Uani . U 1 -1
C12 C -0.3279(8) 0.2909(18) 0.0490(6) 0.0782 0.5000 Uani . U 1 -1
C13 C -0.2561(19) 0.088(2) 0.1022(12) 0.0830 0.5000 Uani . U 1 -1
C14 C -0.0635(10) 0.0691(16) 0.1780(10) 0.0769 0.5000 Uani . U 1 -1
C15 C -0.0996(12) 0.4943(19) 0.1367(11) 0.0957 0.5000 Uani . U 1 -1
H31 H 0.6360 0.2500 0.3450 0.0640 1.0000 Uiso . . . .
H41 H 0.8467 0.2500 0.5613 0.0676 1.0000 Uiso . . . .
H51 H 0.7760 0.2500 0.7569 0.0637 1.0000 Uiso . . . .
H61 H 0.4908 0.2500 0.7436 0.0675 1.0000 Uiso . . . .
H91 H -0.0714 0.1307 0.3432 0.0545 0.5000 Uiso . . 1 -1
H101 H -0.0678 0.4130 0.3530 0.0738 0.5000 Uiso . . 1 -1
H111 H -0.3574 0.5296 0.1316 0.0850 0.5000 Uiso . . 1 -1
H121 H -0.4499 0.2887 0.0327 0.0851 0.5000 Uiso . . 1 -1
H122 H -0.3086 0.3134 -0.0373 0.0851 0.5000 Uiso . . 1 -1
H131 H -0.3129 0.0450 0.1650 0.0867 0.5000 Uiso . . 1 -1
H132 H -0.2853 0.0013 0.0234 0.0867 0.5000 Uiso . . 1 -1
H141 H -0.0355 -0.0622 0.2144 0.0831 0.5000 Uiso . . 1 -1
H142 H -0.0010 0.0985 0.1163 0.0831 0.5000 Uiso . . 1 -1
H151 H -0.0610 0.6296 0.1445 0.1068 0.5000 Uiso . . 1 -1
H152 H -0.0595 0.4258 0.0715 0.1068 0.5000 Uiso . . 1 -1
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C9 4_555 N1 C1 127.4(3) yes
C9 4_555 N1 C8 119.6(3) yes
C1 . N1 C8 111.3(3) yes
C9 4_555 N1 C9 23.5(5) yes
C1 . N1 C9 127.4(3) yes
C8 . N1 C9 119.6(3) yes
N1 . C1 C2 106.1(3) yes
N1 . C1 O1 126.4(4) yes
C2 . C1 O1 127.6(4) yes
C1 . C2 C3 131.3(4) yes
C1 . C2 C7 107.7(3) yes
C3 . C2 C7 121.0(4) yes
C2 . C3 C4 117.7(4) yes
C2 . C3 H31 121.1 no
C4 . C3 H31 121.1 no
C3 . C4 C5 121.2(4) yes
C3 . C4 H41 119.4 no
C5 . C4 H41 119.4 no
C4 . C5 C6 121.1(4) yes
C4 . C5 H51 119.5 no
C6 . C5 H51 119.4 no
C5 . C6 C7 117.3(4) yes
C5 . C6 H61 121.4 no
C7 . C6 H61 121.4 no
C2 . C7 C6 121.6(3) yes
C2 . C7 C8 108.3(3) yes
C6 . C7 C8 130.1(4) yes
C7 . C8 N1 106.6(3) yes
C7 . C8 O2 128.2(4) yes
N1 . C8 O2 125.2(4) yes
N1 . C9 C10 103.7(5) yes
N1 . C9 C14 117.6(5) yes
C10 . C9 C14 117.2(6) yes
N1 . C9 H91 111.2 no
C10 . C9 H91 111.7 no
C14 . C9 H91 95.5 no
C9 . C10 C11 128.9(8) yes
C9 . C10 C15 119.2(9) yes
C11 . C10 C15 55.5(8) yes
C9 . C10 H101 85.1 no
C11 . C10 H101 132.9 no
C15 . C10 H101 141.5 no
C10 . C11 C12 111.5(11) yes
C10 . C11 C15 59.3(8) yes
C12 . C11 C15 109.5(12) yes
C10 . C11 H111 135.1 no
C12 . C11 H111 100.6 no
C15 . C11 H111 136.6 no
C11 . C12 C13 116.0(5) yes
C11 . C12 H121 107.8 no
C13 . C12 H121 107.8 no
C11 . C12 H122 107.8 no
C13 . C12 H122 107.8 no
H121 . C12 H122 109.5 no
C12 . C13 C14 118.3(11) yes
C12 . C13 H131 107.2 no
C14 . C13 H131 107.2 no
C12 . C13 H132 107.2 no
C14 . C13 H132 107.3 no
H131 . C13 H132 109.5 no
C13 . C14 C9 105.8(9) yes
C13 . C14 H141 110.4 no
C9 . C14 H141 110.5 no
C13 . C14 H142 110.3 no
C9 . C14 H142 110.3 no
H141 . C14 H142 109.5 no
C10 . C15 C11 65.2(8) yes
C10 . C15 H151 118.9 no
C11 . C15 H151 118.9 no
C10 . C15 H152 119.2 no
C11 . C15 H152 119.3 no
H151 . C15 H152 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C9 4_555 1.510(6) yes
N1 C1 . 1.397(5) yes
N1 C8 . 1.385(5) yes
N1 C9 . 1.510(6) yes
C1 C2 . 1.489(5) yes
C1 O1 . 1.200(5) yes
C2 C3 . 1.375(5) yes
C2 C7 . 1.381(5) yes
C3 C4 . 1.387(6) yes
C3 H31 . 1.000 no
C4 C5 . 1.377(7) yes
C4 H41 . 1.000 no
C5 C6 . 1.390(6) yes
C5 H51 . 1.000 no
C6 C7 . 1.379(6) yes
C6 H61 . 1.000 no
C7 C8 . 1.478(5) yes
C8 O2 . 1.210(5) yes
C9 C10 . 1.489(11) yes
C9 C14 . 1.446(11) yes
C9 H91 . 1.000 no
C10 C11 . 1.510(16) yes
C10 C15 . 1.429(12) yes
C10 H101 . 1.000 no
C11 C12 . 1.502(14) yes
C11 C15 . 1.37(2) yes
C11 H111 . 1.000 no
C12 C13 . 1.579(17) yes
C12 H121 . 1.000 no
C12 H122 . 1.000 no
C13 C14 . 1.578(16) yes
C13 H131 . 1.000 no
C13 H132 . 0.999 no
C14 H141 . 0.999 no
C14 H142 . 1.001 no
C15 H151 . 1.002 no
C15 H152 . 0.998 no
