#------------------------------------------------------------------------------
#$Date: 2022-05-31 00:53:23 +0300 (Tue, 31 May 2022) $
#$Revision: 275685 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/01/7130157.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_7130157
loop_
_publ_author_name
'Mishra, Manmath'
'Maharana, Prabhat Kumar'
'Karjee, Pallab'
'Punniyamurthy, Tharmalingam'
_publ_section_title
;
 Expedient cobalt-catalyzed stereospecific cascade C-N and C-O bonds
 formation of styrene oxides with hydrazones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01926D
_journal_year                    2022
_chemical_formula_sum            'C22 H20 N2 O2'
_chemical_formula_weight         344.40
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-03-11 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.328(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2857(15)
_cell_length_b                   5.8924(5)
_cell_length_c                   21.571(2)
_cell_measurement_reflns_used    5009
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.10
_cell_measurement_theta_min      2.34
_cell_volume                     1815.3(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19935
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.393
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       Needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.900
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0427
_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)+(0.1000P)²+0.2668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1466
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2373
_reflns_number_total             3187
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc01926d2.cif
_cod_data_source_block           MM_147_OME_TP_0m_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7130157
_shelx_shelxl_version_number     2014/7
_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, 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
O2 O 0.26660(9) 0.03053(19) 0.71990(6) 0.0569(4) Uani 1 1 d . . . . .
O1 O 0.02307(10) 0.4845(3) 0.92351(6) 0.0715(4) Uani 1 1 d . . . . .
N1 N 0.22309(10) 0.3540(2) 0.66311(7) 0.0492(4) Uani 1 1 d . . . . .
N2 N 0.27666(11) 0.2849(3) 0.61441(7) 0.0541(4) Uani 1 1 d . . . . .
C16 C 0.46070(13) 0.2990(3) 0.67460(9) 0.0533(5) Uani 1 1 d . . . . .
H16 H 0.4181 0.4146 0.6822 0.064 Uiso 1 1 calc R U . . .
C8 C 0.22131(12) 0.2325(3) 0.71228(8) 0.0470(4) Uani 1 1 d . . . . .
C11 C 0.43259(12) 0.1121(3) 0.64049(8) 0.0471(4) Uani 1 1 d . . . . .
C7 C 0.16911(12) 0.3039(3) 0.76660(8) 0.0468(4) Uani 1 1 d . . . . .
C17 C 0.27522(13) 0.4243(3) 0.56184(8) 0.0519(5) Uani 1 1 d . . . . .
C10 C 0.33227(13) 0.0784(3) 0.61854(9) 0.0524(5) Uani 1 1 d . . . . .
H10 H 0.3328 0.0084 0.5773 0.063 Uiso 1 1 calc R U . . .
C22 C 0.20261(13) 0.5782(3) 0.55174(8) 0.0530(5) Uani 1 1 d . . . . .
H22 H 0.1537 0.5860 0.5794 0.064 Uiso 1 1 calc R U . . .
C15 C 0.55141(14) 0.3162(3) 0.69761(9) 0.0599(5) Uani 1 1 d . . . . .
H15 H 0.5696 0.4433 0.7205 0.072 Uiso 1 1 calc R U . . .
C9 C 0.28058(14) -0.0797(3) 0.66180(9) 0.0594(5) Uani 1 1 d . . . . .
H9A H 0.2205 -0.1211 0.6432 0.071 Uiso 1 1 calc R U . . .
H9B H 0.3167 -0.2173 0.6683 0.071 Uiso 1 1 calc R U . . .
C2 C 0.06934(13) 0.4361(3) 0.87031(9) 0.0550(5) Uani 1 1 d . . . . .
C5 C 0.11440(14) 0.4977(3) 0.76572(9) 0.0599(5) Uani 1 1 d . . . . .
H5 H 0.1113 0.5856 0.7299 0.072 Uiso 1 1 calc R U . . .
C14 C 0.61462(14) 0.1473(4) 0.68692(10) 0.0653(6) Uani 1 1 d . . . . .
H14 H 0.6755 0.1586 0.7028 0.078 Uiso 1 1 calc R U . . .
C6 C 0.17313(14) 0.1788(3) 0.82112(9) 0.0590(5) Uani 1 1 d . . . . .
H6 H 0.2094 0.0477 0.8230 0.071 Uiso 1 1 calc R U . . .
C12 C 0.49793(15) -0.0562(3) 0.62943(10) 0.0637(5) Uani 1 1 d . . . . .
H12 H 0.4806 -0.1823 0.6059 0.076 Uiso 1 1 calc R U . . .
C21 C 0.20309(16) 0.7195(4) 0.50062(9) 0.0661(6) Uani 1 1 d . . . . .
H21 H 0.1548 0.8237 0.4946 0.079 Uiso 1 1 calc R U . . .
C3 C 0.12466(14) 0.2445(3) 0.87234(9) 0.0642(5) Uani 1 1 d . . . . .
H3 H 0.1292 0.1594 0.9086 0.077 Uiso 1 1 calc R U . . .
C4 C 0.06440(14) 0.5639(3) 0.81657(9) 0.0628(5) Uani 1 1 d . . . . .
H4 H 0.0275 0.6939 0.8147 0.075 Uiso 1 1 calc R U . . .
C13 C 0.58781(15) -0.0390(4) 0.65270(11) 0.0705(6) Uani 1 1 d . . . . .
H13 H 0.6307 -0.1539 0.6453 0.085 Uiso 1 1 calc R U . . .
C18 C 0.34610(15) 0.4128(4) 0.51897(9) 0.0686(6) Uani 1 1 d . . . . .
H18 H 0.3947 0.3091 0.5245 0.082 Uiso 1 1 calc R U . . .
C1 C -0.03032(16) 0.6865(4) 0.92542(11) 0.0776(7) Uani 1 1 d . . . . .
H1A H 0.0097 0.8146 0.9187 0.116 Uiso 1 1 calc R U . . .
H1B H -0.0585 0.6999 0.9652 0.116 Uiso 1 1 calc R U . . .
H1C H -0.0784 0.6820 0.8936 0.116 Uiso 1 1 calc R U . . .
C20 C 0.27358(19) 0.7085(4) 0.45867(10) 0.0797(7) Uani 1 1 d . . . . .
H20 H 0.2732 0.8039 0.4243 0.096 Uiso 1 1 calc R U . . .
C19 C 0.34456(18) 0.5552(4) 0.46805(10) 0.0809(7) Uani 1 1 d . . . . .
H19 H 0.3925 0.5467 0.4397 0.097 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 0.0033 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
_geom_angle_publ_flag
C8 O2 C9 111.49(14) . . ?
C2 O1 C1 118.13(16) . . ?
C8 N1 N2 119.28(14) . . ?
N1 N2 C17 116.55(14) . . ?
N1 N2 C10 120.90(14) . . ?
C17 N2 C10 122.55(15) . . ?
C11 C16 C15 120.65(17) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
N1 C8 O2 124.74(16) . . ?
N1 C8 C7 121.47(15) . . ?
O2 C8 C7 113.79(14) . . ?
C16 C11 C12 118.31(17) . . ?
C16 C11 C10 122.28(15) . . ?
C12 C11 C10 119.30(16) . . ?
C5 C7 C6 117.55(17) . . ?
C5 C7 C8 121.59(16) . . ?
C6 C7 C8 120.86(16) . . ?
C18 C17 C22 118.68(17) . . ?
C18 C17 N2 120.91(17) . . ?
C22 C17 N2 120.41(16) . . ?
N2 C10 C11 114.95(14) . . ?
N2 C10 C9 106.11(14) . . ?
C11 C10 C9 110.98(15) . . ?
N2 C10 H10 108.2 . . ?
C11 C10 H10 108.2 . . ?
C9 C10 H10 108.2 . . ?
C21 C22 C17 120.02(19) . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C14 C15 C16 120.27(18) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
O2 C9 C10 109.83(14) . . ?
O2 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
O2 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
O1 C2 C3 115.61(17) . . ?
O1 C2 C4 125.00(17) . . ?
C3 C2 C4 119.39(18) . . ?
C4 C5 C7 121.68(18) . . ?
C4 C5 H5 119.2 . . ?
C7 C5 H5 119.2 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C3 C6 C7 121.32(17) . . ?
C3 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C13 C12 C11 120.83(18) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C20 C21 C22 121.0(2) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C6 C3 C2 120.34(18) . . ?
C6 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C2 119.71(18) . . ?
C5 C4 H4 120.1 . . ?
C2 C4 H4 120.1 . . ?
C12 C13 C14 120.21(19) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C19 C20 C21 119.1(2) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C8 1.363(2) . ?
O2 C9 1.430(2) . ?
O1 C2 1.368(2) . ?
O1 C1 1.415(2) . ?
N1 C8 1.280(2) . ?
N1 N2 1.376(2) . ?
N2 C17 1.400(2) . ?
N2 C10 1.454(2) . ?
C16 C11 1.379(2) . ?
C16 C15 1.381(3) . ?
C16 H16 0.9300 . ?
C8 C7 1.465(2) . ?
C11 C12 1.386(2) . ?
C11 C10 1.512(3) . ?
C7 C5 1.384(3) . ?
C7 C6 1.388(2) . ?
C17 C18 1.389(3) . ?
C17 C22 1.391(3) . ?
C10 C9 1.522(3) . ?
C10 H10 0.9800 . ?
C22 C21 1.382(3) . ?
C22 H22 0.9300 . ?
C15 C14 1.367(3) . ?
C15 H15 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C2 C3 1.378(3) . ?
C2 C4 1.383(3) . ?
C5 C4 1.379(3) . ?
C5 H5 0.9300 . ?
C14 C13 1.372(3) . ?
C14 H14 0.9300 . ?
C6 C3 1.373(3) . ?
C6 H6 0.9300 . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C21 C20 1.371(3) . ?
C21 H21 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C13 H13 0.9300 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C20 C19 1.370(3) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
