#------------------------------------------------------------------------------
#$Date: 2017-05-06 00:51:19 +0300 (Sat, 06 May 2017) $
#$Revision: 196363 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/48/1544823.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_1544823
loop_
_publ_author_name
'Barsu, Nagaraju'
'Bolli, Shyam Kumar'
'Sundararaju, Basker'
_publ_section_title
;
 Cobalt catalyzed carbonylation of unactivated C(sp(3))-H bonds.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              2431
_journal_page_last               2435
_journal_paper_doi               10.1039/c6sc05026c
_journal_volume                  8
_journal_year                    2017
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_chemical_name_systematic        succinimide-piv
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2016-09-28 deposited with the CCDC.
2016-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 101.968(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   8.730(5)
_cell_length_b                   13.396(5)
_cell_length_c                   11.372(5)
_cell_measurement_reflns_used    3211
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.4
_cell_volume                     1301.0(11)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12694
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.316
_diffrn_reflns_theta_min         2.380
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0570
_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)+(0.0595P)²+0.4022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2050
_reflns_number_total             3211
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6sc05026c2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;Adding full bibliography for 1544822--1544823.cif.

 Adding full bibliography for 1544822--1544823.cif.
;
_cod_database_code               1544823
_shelx_shelxl_version_number     2016/4
_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.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.5917(2) 0.27125(15) 0.41669(18) 0.0227(5) Uani 1 1 d . .
H1 H 0.552621 0.276789 0.486542 0.027 Uiso 1 1 calc R U
C2 C 0.7117(2) 0.20173(16) 0.41093(19) 0.0269(5) Uani 1 1 d . .
H2 H 0.753411 0.162858 0.477663 0.032 Uiso 1 1 calc R U
C3 C 0.7663(2) 0.19162(15) 0.30806(19) 0.0255(5) Uani 1 1 d . .
H3 H 0.841885 0.143606 0.303725 0.031 Uiso 1 1 calc R U
C4 C 0.7096(2) 0.25329(15) 0.20738(18) 0.0216(4) Uani 1 1 d . .
C5 C 0.7655(2) 0.24850(15) 0.10003(19) 0.0256(5) Uani 1 1 d . .
H5 H 0.839401 0.200773 0.090698 0.031 Uiso 1 1 calc R U
C6 C 0.7104(2) 0.31434(15) 0.00986(18) 0.0263(5) Uani 1 1 d . .
H6 H 0.746890 0.312452 -0.061359 0.032 Uiso 1 1 calc R U
C7 C 0.5986(2) 0.38465(15) 0.02586(17) 0.0243(5) Uani 1 1 d . .
H7 H 0.564326 0.429906 -0.036033 0.029 Uiso 1 1 calc R U
C8 C 0.5930(2) 0.32600(14) 0.21381(17) 0.0184(4) Uani 1 1 d . .
C9 C 0.5332(2) 0.32997(14) 0.32049(17) 0.0190(4) Uani 1 1 d . .
C10 C 0.2504(2) 0.37151(15) 0.27922(16) 0.0187(4) Uani 1 1 d . .
C11 C 0.1489(2) 0.46339(14) 0.28188(17) 0.0207(4) Uani 1 1 d . .
C12 C 0.2663(2) 0.54232(14) 0.34350(19) 0.0243(5) Uani 1 1 d . .
H12A H 0.256233 0.603074 0.296104 0.029 Uiso 1 1 calc R U
H12B H 0.247705 0.558098 0.422623 0.029 Uiso 1 1 calc R U
C13 C 0.4261(2) 0.49800(15) 0.35333(17) 0.0217(4) Uani 1 1 d . .
C15 C 0.0793(3) 0.49065(17) 0.15100(19) 0.0335(5) Uani 1 1 d . .
H15A H 0.014088 0.548601 0.148671 0.050 Uiso 1 1 calc R U
H15B H 0.162426 0.504579 0.109798 0.050 Uiso 1 1 calc R U
H15C H 0.017836 0.435853 0.112445 0.050 Uiso 1 1 calc R U
C16 C 0.0205(3) 0.44059(18) 0.3502(2) 0.0356(6) Uani 1 1 d . .
H16A H -0.042993 0.498913 0.351499 0.053 Uiso 1 1 calc R U
H16B H -0.043429 0.386987 0.311181 0.053 Uiso 1 1 calc R U
H16C H 0.067001 0.421467 0.431115 0.053 Uiso 1 1 calc R U
N1 N 0.53775(18) 0.39144(12) 0.12300(14) 0.0211(4) Uani 1 1 d . .
N2 N 0.40665(18) 0.39717(11) 0.32366(14) 0.0190(4) Uani 1 1 d . .
O1 O 0.20775(16) 0.28974(10) 0.24170(12) 0.0263(4) Uani 1 1 d . .
2 O 0.55231(16) 0.53743(10) 0.38300(13) 0.0293(4) Uani 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
C9 C1 C2 120.18(19)
C3 C2 C1 120.09(19)
C2 C3 C4 120.80(19)
C5 C4 C3 123.30(18)
C5 C4 C8 117.17(18)
C3 C4 C8 119.50(18)
C6 C5 C4 119.46(19)
C5 C6 C7 119.08(19)
N1 C7 C6 124.57(18)
N1 C8 C9 119.23(17)
N1 C8 C4 123.09(18)
C9 C8 C4 117.68(17)
C1 C9 C8 121.58(18)
C1 C9 N2 120.48(17)
C8 C9 N2 117.93(17)
O1 C10 N2 123.98(18)
O1 C10 C11 127.12(17)
N2 C10 C11 108.86(16)
C10 C11 C16 109.99(17)
C10 C11 C15 106.81(16)
C16 C11 C15 111.03(18)
C10 C11 C12 103.29(15)
C16 C11 C12 113.41(17)
C15 C11 C12 111.83(17)
C13 C12 C11 106.48(16)
2 C13 N2 123.41(19)
2 C13 C12 129.06(19)
N2 C13 C12 107.52(16)
C7 N1 C8 116.58(17)
C13 N2 C10 112.77(16)
C13 N2 C9 124.04(16)
C10 N2 C9 122.50(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C9 1.358(3)
C1 C2 1.414(3)
C2 C3 1.358(3)
C3 C4 1.415(3)
C4 C5 1.407(3)
C4 C8 1.421(3)
C5 C6 1.362(3)
C6 C7 1.396(3)
C7 N1 1.324(3)
C8 N1 1.364(2)
C8 C9 1.418(3)
C9 N2 1.431(2)
C10 O1 1.206(2)
C10 N2 1.396(2)
C10 C11 1.521(3)
C11 C16 1.521(3)
C11 C15 1.531(3)
C11 C12 1.537(3)
C12 C13 1.499(3)
C13 2 1.205(2)
C13 N2 1.394(3)
