#------------------------------------------------------------------------------
#$Date: 2015-07-03 21:18:52 +0300 (Fri, 03 Jul 2015) $
#$Revision: 139962 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/74/7117410.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_7117410
loop_
_publ_author_name
'Yanxin Yang'
'Maotong Xu'
'Datong Song'
_publ_section_title
;
 Organocatalysts with carbon-centered activity for CO2 reduction with
 boranes
;
_journal_name_full               Chem.Commun.
_journal_page_first              11293
_journal_paper_doi               10.1039/C5cc04337A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C12 H13 N O2'
_chemical_formula_sum            'C12 H13 N O2'
_chemical_formula_weight         203.23
_chemical_name_systematic
;
 ?
;
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-05-08 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.210(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1916(10)
_cell_length_b                   12.6389(14)
_cell_length_c                   9.1878(10)
_cell_measurement_reflns_used    9133
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.511
_cell_measurement_theta_min      2.251
_cell_volume                     1050.5(2)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9133
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         2.251
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0594P)²+0.0344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1107
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                1633
_reflns_number_total             2412
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc04337a2.cif
_cod_data_source_block           3
_cod_database_code               7117410
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.93736(12) 0.93704(8) 0.12947(11) 0.0258(3) Uani 1 1 d . . . . .
O2 O 0.93679(13) 1.11307(8) 0.09477(12) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.74606(13) 0.97399(9) 0.64636(13) 0.0207(3) Uani 1 1 d . . . . .
C4 C 0.82918(15) 0.97030(11) 0.40984(16) 0.0187(3) Uani 1 1 d . . . . .
C5 C 0.77852(15) 1.02744(11) 0.52737(16) 0.0195(3) Uani 1 1 d . . . . .
C10 C 0.69847(18) 1.03205(13) 0.76928(18) 0.0234(4) Uani 1 1 d . . . . .
C8 C 0.85533(16) 1.04816(11) 0.30493(16) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.75784(17) 0.86673(12) 0.65225(18) 0.0252(4) Uani 1 1 d . . . . .
C9 C 0.91150(16) 1.02775(11) 0.17285(17) 0.0208(3) Uani 1 1 d . . . . .
C3 C 0.84481(17) 0.86143(11) 0.42032(18) 0.0220(3) Uani 1 1 d . . . . .
C2 C 0.80633(17) 0.81040(12) 0.54203(18) 0.0251(4) Uani 1 1 d . . . . .
C7 C 0.82177(17) 1.14719(12) 0.36104(18) 0.0250(4) Uani 1 1 d . . . . .
C6 C 0.77427(17) 1.13621(12) 0.49557(18) 0.0241(4) Uani 1 1 d . . . . .
C11 C 0.53364(18) 1.05327(14) 0.7419(2) 0.0304(4) Uani 1 1 d . . . . .
C12 C 0.4922(2) 1.12180(17) 0.8650(2) 0.0399(5) Uani 1 1 d . . . . .
H1 H 0.7301(16) 0.8355(12) 0.7421(18) 0.022(4) Uiso 1 1 d . . . . .
H3 H 0.8826(16) 0.8264(12) 0.3449(17) 0.024(4) Uiso 1 1 d . . . . .
H2 H 0.8178(18) 0.7338(14) 0.5553(18) 0.036(5) Uiso 1 1 d . . . . .
H10B H 0.7589(18) 1.1010(14) 0.7828(18) 0.033(5) Uiso 1 1 d . . . . .
H11B H 0.4760(18) 0.9862(14) 0.7328(19) 0.034(5) Uiso 1 1 d . . . . .
H11A H 0.5031(18) 1.0890(13) 0.6429(19) 0.033(5) Uiso 1 1 d . . . . .
H10A H 0.7280(17) 0.9916(12) 0.8642(18) 0.026(4) Uiso 1 1 d . . . . .
H12A H 0.532(2) 1.0923(15) 0.966(2) 0.050(6) Uiso 1 1 d . . . . .
H6 H 0.7467(17) 1.1935(14) 0.5581(19) 0.035(5) Uiso 1 1 d . . . . .
H2A H 0.981(2) 1.0944(18) 0.009(3) 0.071(7) Uiso 1 1 d . . . . .
H7 H 0.8303(19) 1.2128(15) 0.3093(19) 0.041(5) Uiso 1 1 d . . . . .
H12B H 0.380(2) 1.1259(16) 0.855(2) 0.064(6) Uiso 1 1 d . . . . .
H12C H 0.535(2) 1.1951(18) 0.867(2) 0.068(7) Uiso 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C5 119.92(13) . .
C1 N1 C10 119.81(13) . .
C5 N1 C10 120.27(12) . .
C3 C4 C8 134.75(14) . .
C3 C4 C5 119.24(14) . .
C8 C4 C5 105.99(12) . .
N1 C5 C6 130.56(14) . .
N1 C5 C4 119.86(13) . .
C6 C5 C4 109.57(13) . .
N1 C10 C11 112.59(13) . .
C7 C8 C9 127.51(14) . .
C7 C8 C4 106.95(13) . .
C9 C8 C4 125.48(13) . .
N1 C1 C2 121.37(14) . .
O1 C9 O2 120.47(14) . .
O1 C9 C8 123.78(13) . .
O2 C9 C8 115.75(13) . .
C4 C3 C2 118.61(14) . .
C1 C2 C3 120.94(14) . .
C6 C7 C8 111.14(14) . .
C7 C6 C5 106.34(13) . .
C10 C11 C12 110.55(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C9 1.2503(17) .
O2 C9 1.3383(17) .
N1 C1 1.3603(19) .
N1 C5 1.3625(19) .
N1 C10 1.4766(19) .
C4 C3 1.385(2) .
C4 C8 1.427(2) .
C4 C5 1.443(2) .
C5 C6 1.405(2) .
C10 C11 1.515(2) .
C8 C7 1.408(2) .
C8 C9 1.424(2) .
C1 C2 1.375(2) .
C3 C2 1.390(2) .
C7 C6 1.389(2) .
C11 C12 1.525(2) .
