#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:56:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180203 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/97/7109728.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_7109728
loop_
_publ_author_name
'Amit Choudhary'
'Charles G. Fry'
'Kimberli J. Kamer'
'Ronald T. Raines'
_publ_section_title
;
 An n-->pi^*^ interaction reduces the electrophilicity of the acceptor
 carbonyl group
;
_journal_name_full               Chem.Commun.
_journal_page_first              8166
_journal_paper_doi               10.1039/c3cc44573a
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C7 H12 N2 O2'
_chemical_formula_weight         156.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
manual editing of the CIF file 
created by SHELXTL Ver. 6.10
and processed with modiCIfer-03272007. 
;
_cell_angle_alpha                90
_cell_angle_beta                 107.3630(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0221(4)
_cell_length_b                   5.7680(2)
_cell_length_c                   10.4415(3)
_cell_measurement_reflns_used    8733
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.91
_cell_measurement_theta_min      7.13
_cell_volume                     748.54(4)
_computing_cell_refinement       'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 Ver. 2.1-4 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT Ver. 7.24A'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.60° ω and 0.6° φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0081
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10524
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.914
_diffrn_reflns_theta_min         7.126
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  0.8917
_exptl_absorpt_correction_T_min  0.7316
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2007)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     52
_refine_ls_number_reflns         686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.194
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0616P)²+0.4217P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                682
_reflns_number_total             686
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c3cc44573a.txt
_cod_data_source_block           raines47_0m
_cod_database_code               7109728
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.732
_shelx_estimated_absorpt_t_max   0.892
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.37320(7) 0.66580(15) 0.40564(9) 0.0220(3) Uani 1 1 d . . .
N1 N 0.43787(8) 0.95341(16) 0.30634(10) 0.0181(3) Uani 1 1 d . . .
C3 C 0.5000 0.7942(3) 0.2500 0.0169(4) Uani 1 2 d S T P
H3A H 0.4525 0.6949 0.1796 0.020 Uiso 0.5 1 calc R U P
H3B H 0.5475 0.6949 0.3204 0.020 Uiso 0.5 1 calc R U P
C2 C 0.37533(9) 0.8737(2) 0.37928(11) 0.0164(3) Uani 1 1 d . . .
C1 C 0.30736(10) 1.0513(2) 0.42237(12) 0.0200(4) Uani 1 1 d . . .
H1A H 0.2522 1.1105 0.3433 0.030 Uiso 1 1 calc R U .
H1B H 0.3531 1.1795 0.4681 0.030 Uiso 1 1 calc R U .
H1C H 0.2726 0.9792 0.4837 0.030 Uiso 1 1 calc R U .
C4 C 0.44592(10) 1.1933(2) 0.26376(13) 0.0201(4) Uani 1 1 d . . .
H4A H 0.4451 1.3045 0.3357 0.024 Uiso 1 1 calc R U .
H4B H 0.3867 1.2314 0.1819 0.024 Uiso 1 1 calc R U .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 N1 C3 120.88(10) . .
C2 N1 C4 127.00(10) . .
C3 N1 C4 111.91(9) . .
N1 C3 N1 101.98(13) . 2_655
N1 C3 H3A 111.4 . .
N1 C3 H3A 111.4 2_655 .
N1 C3 H3B 111.4 . .
N1 C3 H3B 111.4 2_655 .
H3A C3 H3B 109.2 . .
O1 C2 N1 120.99(11) . .
O1 C2 C1 122.69(11) . .
N1 C2 C1 116.31(11) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C4 C4 102.21(7) . 2_655
N1 C4 H4A 111.3 . .
C4 C4 H4A 111.3 2_655 .
N1 C4 H4B 111.3 . .
C4 C4 H4B 111.3 2_655 .
H4A C4 H4B 109.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.2323(15) .
N1 C2 1.3510(15) .
N1 C3 1.4586(14) .
N1 C4 1.4666(15) .
C3 N1 1.4587(14) 2_655
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C2 C1 1.5077(16) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C4 C4 1.519(2) 2_655
C4 H4A 0.9900 .
C4 H4B 0.9900 .
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
_geom_torsion_site_symmetry_4
C2 N1 C3 N1 -174.29(12) 2_655
C4 N1 C3 N1 10.63(6) 2_655
C3 N1 C2 O1 3.58(16) .
C4 N1 C2 O1 177.87(11) .
C3 N1 C2 C1 -174.87(8) .
C4 N1 C2 C1 -0.58(17) .
C2 N1 C4 C4 158.90(12) 2_655
C3 N1 C4 C4 -26.38(14) 2_655
