#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:45:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178822 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/76/4107603.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_4107603
loop_
_publ_author_name
'Maksim Royzen'
'Glenn P. A. Yap'
'Joseph M. Fox'
_publ_section_title
;
 A Photochemical Synthesis of Functionalized trans-Cyclooctenes Driven by
 Metal Complexation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3760
_journal_page_last               3761
_journal_paper_doi               10.1021/ja8001919
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C9 H11 N O2'
_chemical_formula_weight         165.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.203(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.891(5)
_cell_length_b                   11.639(8)
_cell_length_c                   10.710(7)
_cell_measurement_reflns_used    909
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      2.59
_cell_volume                     856.7(10)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       ω
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9267
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.59
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1986
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0774
_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)+(0.1015P)²+0.6900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2076
_refine_ls_wR_factor_ref         0.2201
_reflns_number_gt                1673
_reflns_number_total             1986
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8001919-file003.cif
_cod_data_source_block           joef058
_cod_original_cell_volume        856.6(10)
_cod_database_code               4107603
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3690(4) 0.8280(2) 0.9456(3) 0.0665(10) Uani 0.603(2) 1 d PD A 1
C2 C 0.4113(5) 0.7067(3) 0.9668(4) 0.0394(7) Uani 0.603(2) 1 d PD A 1
H2A H 0.3148 0.6510 0.9430 0.047 Uiso 0.603(2) 1 calc PR A 1
C3 C 0.5832(6) 0.6725(4) 1.0189(4) 0.0412(8) Uani 0.603(2) 1 d PD A 1
H3A H 0.6280 0.7056 1.0969 0.049 Uiso 0.603(2) 1 calc PR A 1
C4 C 0.7088(7) 0.5863(4) 0.9629(5) 0.0476(10) Uani 0.603(2) 1 d PD A 1
H4A H 0.6316 0.5353 0.9043 0.057 Uiso 0.603(2) 1 calc PR A 1
H4B H 0.7788 0.5388 1.0284 0.057 Uiso 0.603(2) 1 calc PR A 1
C5 C 0.8525(7) 0.6607(5) 0.8927(5) 0.0481(11) Uani 0.603(2) 1 d PD A 1
H5A H 0.9298 0.7077 0.9553 0.058 Uiso 0.603(2) 1 calc PR A 1
H5B H 0.9440 0.6085 0.8536 0.058 Uiso 0.603(2) 1 calc PR A 1
C6 C 0.7627(7) 0.7415(4) 0.7907(4) 0.0424(9) Uani 0.603(2) 1 d PD A 1
H6A H 0.6570 0.6984 0.7439 0.051 Uiso 0.603(2) 1 calc PR A 1
H6B H 0.8638 0.7561 0.7316 0.051 Uiso 0.603(2) 1 calc PR A 1
C7 C 0.6776(5) 0.8603(3) 0.8249(3) 0.0382(7) Uani 0.603(2) 1 d PD A 1
H7A H 0.7430 0.8834 0.9064 0.046 Uiso 0.603(2) 1 calc PR A 1
H7B H 0.7182 0.9161 0.7621 0.046 Uiso 0.603(2) 1 calc PR A 1
C8 C 0.4604(3) 0.8767(3) 0.8346(2) 0.0482(7) Uani 0.603(2) 1 d PD A 1
C9 C 0.2022(3) 0.9884(2) 0.8732(2) 0.0402(5) Uani 1 1 d . A .
N1 N 0.2016(3) 0.8977(2) 0.9510(2) 0.0493(6) Uani 1 1 d . . .
H1 H 0.119(5) 0.899(3) 1.013(3) 0.059 Uiso 1 1 d . . .
O1 O 0.3556(3) 0.97973(16) 0.80170(19) 0.0620(6) Uani 1 1 d . . .
O2 O 0.0904(2) 1.06911(16) 0.86424(16) 0.0480(5) Uani 1 1 d . . .
C1' C 0.3690(4) 0.8280(2) 0.9456(3) 0.0665(10) Uani 0.397(2) 1 d PD A 2
C2' C 0.4871(8) 0.7588(5) 1.0011(6) 0.0394(7) Uani 0.397(2) 1 d PD A 2
H2'A H 0.5369 0.7783 1.0834 0.047 Uiso 0.397(2) 1 calc PR A 2
C3' C 0.5473(9) 0.6604(6) 0.9534(6) 0.0412(8) Uani 0.397(2) 1 d PD A 2
H3'A H 0.4535 0.6091 0.9154 0.049 Uiso 0.397(2) 1 calc PR A 2
C4' C 0.7583(12) 0.6282(7) 0.9579(9) 0.0476(10) Uani 0.397(2) 1 d PD A 2
H4'A H 0.7758 0.5442 0.9678 0.057 Uiso 0.397(2) 1 calc PR A 2
H4'B H 0.8337 0.6679 1.0273 0.057 Uiso 0.397(2) 1 calc PR A 2
C5' C 0.8199(12) 0.6692(8) 0.8296(8) 0.0481(11) Uani 0.397(2) 1 d PD A 2
H5'A H 0.9604 0.6530 0.8257 0.058 Uiso 0.397(2) 1 calc PR A 2
H5'B H 0.7491 0.6226 0.7637 0.058 Uiso 0.397(2) 1 calc PR A 2
C6' C 0.7846(10) 0.7973(7) 0.7983(7) 0.0424(9) Uani 0.397(2) 1 d PD A 2
H6'A H 0.8131 0.8417 0.8763 0.051 Uiso 0.397(2) 1 calc PR A 2
H6'B H 0.8814 0.8208 0.7393 0.051 Uiso 0.397(2) 1 calc PR A 2
C7' C 0.5823(8) 0.8344(5) 0.7416(5) 0.0382(7) Uani 0.397(2) 1 d PD A 2
H7'A H 0.5981 0.8951 0.6785 0.046 Uiso 0.397(2) 1 calc PR A 2
H7'B H 0.5178 0.7679 0.6984 0.046 Uiso 0.397(2) 1 calc PR A 2
C8' C 0.4604(3) 0.8767(3) 0.8346(2) 0.0482(7) Uani 0.397(2) 1 d PD A 2
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
N1 C1 C2 134.8(3)
N1 C1 C8 101.9(2)
C2 C1 C8 113.6(3)
C3 C2 C1 121.1(4)
C3 C2 H2A 119.5
C1 C2 H2A 119.5
C2 C3 C4 124.1(4)
C2 C3 H3A 117.9
C4 C3 H3A 117.9
C3 C4 C5 103.3(4)
C3 C4 H4A 111.1
C5 C4 H4A 111.1
C3 C4 H4B 111.1
C5 C4 H4B 111.1
H4A C4 H4B 109.1
C6 C5 C4 116.6(4)
C6 C5 H5A 108.1
C4 C5 H5A 108.1
C6 C5 H5B 108.1
C4 C5 H5B 108.1
H5A C5 H5B 107.3
C5 C6 C7 121.1(4)
C5 C6 H6A 107.1
C7 C6 H6A 107.1
C5 C6 H6B 107.1
C7 C6 H6B 107.1
H6A C6 H6B 106.8
C8 C7 C6 121.1(3)
C8 C7 H7A 107.0
C6 C7 H7A 107.0
C8 C7 H7B 107.0
C6 C7 H7B 107.0
H7A C7 H7B 106.8
O1 C8 C1 106.2(2)
O1 C8 C7 124.8(2)
C1 C8 C7 118.7(3)
O2 C9 N1 128.7(2)
O2 C9 O1 122.0(2)
N1 C9 O1 109.2(2)
C9 N1 C1 112.7(2)
C9 N1 H1 118(2)
C1 N1 H1 126(2)
C9 O1 C8 108.93(19)
C3' C2' H2'A 117.4
C2' C3' C4' 122.1(7)
C2' C3' H3'A 119.0
C4' C3' H3'A 119.0
C3' C4' C5' 102.9(7)
C3' C4' H4'A 111.2
C5' C4' H4'A 111.2
C3' C4' H4'B 111.2
C5' C4' H4'B 111.2
H4'A C4' H4'B 109.1
C6' C5' C4' 116.3(7)
C6' C5' H5'A 108.2
C4' C5' H5'A 108.2
C6' C5' H5'B 108.2
C4' C5' H5'B 108.2
H5'A C5' H5'B 107.4
C7' C6' C5' 118.7(6)
C7' C6' H6'A 107.6
C5' C6' H6'A 107.6
C7' C6' H6'B 107.6
C5' C6' H6'B 107.6
H6'A C6' H6'B 107.1
C6' C7' H7'A 109.1
C6' C7' H7'B 109.1
H7'A C7' H7'B 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.415(3)
C1 C2 1.456(5)
C1 C8 1.497(3)
C2 C3 1.333(6)
C2 H2A 0.9500
C3 C4 1.481(6)
C3 H3A 0.9500
C4 C5 1.551(7)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.537(7)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.556(6)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.520(4)
C7 H7A 0.9900
C7 H7B 0.9900
C8 O1 1.430(4)
C9 O2 1.214(3)
C9 N1 1.345(3)
C9 O1 1.354(3)
N1 H1 0.91(3)
C2' C3' 1.332(8)
C2' H2'A 0.9500
C3' C4' 1.499(9)
C3' H3'A 0.9500
C4' C5' 1.543(10)
C4' H4'A 0.9900
C4' H4'B 0.9900
C5' C6' 1.544(11)
C5' H5'A 0.9900
C5' H5'B 0.9900
C6' C7' 1.541(9)
C6' H6'A 0.9900
C6' H6'B 0.9900
C7' H7'A 0.9900
C7' H7'B 0.9900
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
_geom_hbond_site_symmetry_A
N1 H1 O2 0.91(3) 2.06(3) 2.949(3) 168(3) 3_577
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
N1 C1 C2 C3 -144.2(4)
C8 C1 C2 C3 77.3(5)
C1 C2 C3 C4 -126.4(4)
C2 C3 C4 C5 95.7(5)
C3 C4 C5 C6 -59.0(6)
C4 C5 C6 C7 81.4(6)
C5 C6 C7 C8 -98.5(5)
N1 C1 C8 O1 9.5(3)
C2 C1 C8 O1 160.8(3)
N1 C1 C8 C7 156.2(3)
C2 C1 C8 C7 -52.5(4)
C6 C7 C8 O1 -146.2(3)
C6 C7 C8 C1 73.7(4)
O2 C9 N1 C1 -172.5(3)
O1 C9 N1 C1 6.5(3)
C2 C1 N1 C9 -151.6(4)
C8 C1 N1 C9 -9.9(3)
O2 C9 O1 C8 179.4(2)
N1 C9 O1 C8 0.3(3)
C1 C8 O1 C9 -6.4(3)
C7 C8 O1 C9 -150.5(3)
C2' C3' C4' C5' -94.9(8)
C3' C4' C5' C6' 56.3(9)
C4' C5' C6' C7' -84.5(9)
