#------------------------------------------------------------------------------
#$Date: 2022-07-07 00:54:47 +0300 (Thu, 07 Jul 2022) $
#$Revision: 276698 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/03/7130328.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_7130328
loop_
_publ_author_name
'Karjee, Pallab'
'Mishra, Manmath'
'Debnath, Bijoy'
'Punniyamurthy, Tharmalingam'
_publ_section_title
;
 Expedient Ni(OTf)2/visible light photoredox-catalyzed annulation of
 donor-acceptor cyclopropanes with cyclic secondary amines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02941C
_journal_year                    2022
_chemical_formula_sum            'C26 H25 N O4'
_chemical_formula_weight         415.47
_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
;
2022-04-01 deposited with the CCDC.	2022-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.892(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1009(6)
_cell_length_b                   7.6217(3)
_cell_length_c                   19.2497(7)
_cell_measurement_reflns_used    7462
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.85
_cell_measurement_theta_min      2.44
_cell_volume                     2210.43(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0701
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            56496
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         1.352
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0461
_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)+(0.0500P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2799
_reflns_number_total             3907
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02941c2.cif
_cod_data_source_block           PK-233
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7130328
_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
C6 C 0.57768(12) 0.6873(2) 0.29465(9) 0.0410(4) Uani 1 1 d . . . . .
C5 C 0.61562(12) 0.5654(2) 0.34346(10) 0.0443(4) Uani 1 1 d . . . . .
C10 C 0.44404(11) 0.7009(2) 0.35864(9) 0.0402(4) Uani 1 1 d . . . . .
C21 C 0.23800(11) 0.8327(2) 0.43784(10) 0.0410(4) Uani 1 1 d . . . . .
H21 H 0.2215 0.9321 0.4074 0.049 Uiso 1 1 calc R U . . .
C7 C 0.49138(12) 0.7539(2) 0.30428(10) 0.0444(5) Uani 1 1 d . . . . .
H7 H 0.4665 0.8355 0.2728 0.053 Uiso 1 1 calc R U . . .
C11 C 0.35162(12) 0.7702(3) 0.36668(10) 0.0461(5) Uani 1 1 d . . . . .
H11 H 0.3425 0.8756 0.3380 0.055 Uiso 1 1 calc R U . . .
C22 C 0.20581(11) 0.6625(2) 0.39914(9) 0.0418(4) Uani 1 1 d . . . . .
C20 C 0.20946(12) 0.8768(2) 0.50962(10) 0.0419(4) Uani 1 1 d . . . . .
C15 C 0.27115(13) 0.9463(3) 0.55955(10) 0.0498(5) Uani 1 1 d . . . . .
C1 C 0.62747(13) 0.7399(3) 0.23839(11) 0.0539(5) Uani 1 1 d . . . . .
H1 H 0.6030 0.8194 0.2058 0.065 Uiso 1 1 calc R U . . .
C9 C 0.48257(13) 0.5772(3) 0.40648(10) 0.0510(5) Uani 1 1 d . . . . .
H9 H 0.4506 0.5390 0.4432 0.061 Uiso 1 1 calc R U . . .
C8 C 0.56558(13) 0.5135(3) 0.39953(11) 0.0545(5) Uani 1 1 d . . . . .
H8 H 0.5900 0.4343 0.4322 0.065 Uiso 1 1 calc R U . . .
C2 C 0.71023(15) 0.6760(3) 0.23132(12) 0.0614(6) Uani 1 1 d . . . . .
H2 H 0.7423 0.7132 0.1945 0.074 Uiso 1 1 calc R U . . .
C23 C 0.11583(13) 0.6839(3) 0.35979(10) 0.0506(5) Uani 1 1 d . . . . .
C24 C 0.20481(13) 0.5053(3) 0.44819(11) 0.0522(5) Uani 1 1 d . . . . .
C13 C 0.37942(13) 0.9702(3) 0.46645(12) 0.0572(6) Uani 1 1 d . . . . .
H13A H 0.3547 1.0739 0.4432 0.069 Uiso 1 1 calc R U . . .
H13B H 0.4422 0.9645 0.4589 0.069 Uiso 1 1 calc R U . . .
C4 C 0.70200(13) 0.5002(3) 0.33405(12) 0.0589(6) Uani 1 1 d . . . . .
H4 H 0.7278 0.4196 0.3656 0.071 Uiso 1 1 calc R U . . .
C19 C 0.12087(13) 0.8626(3) 0.52586(11) 0.0519(5) Uani 1 1 d . . . . .
H19 H 0.0786 0.8214 0.4924 0.062 Uiso 1 1 calc R U . . .
C12 C 0.27806(12) 0.6372(3) 0.34606(11) 0.0595(6) Uani 1 1 d . . . . .
H12A H 0.3012 0.5185 0.3485 0.071 Uiso 1 1 calc R U . . .
H12B H 0.2535 0.6593 0.2990 0.071 Uiso 1 1 calc R U . . .
C18 C 0.09512(15) 0.9090(3) 0.59111(12) 0.0647(6) Uani 1 1 d . . . . .
H18 H 0.0361 0.8981 0.6013 0.078 Uiso 1 1 calc R U . . .
C3 C 0.74749(14) 0.5547(3) 0.27914(13) 0.0634(6) Uani 1 1 d . . . . .
H3 H 0.8040 0.5106 0.2735 0.076 Uiso 1 1 calc R U . . .
C14 C 0.36643(14) 0.9794(3) 0.54327(12) 0.0631(6) Uani 1 1 d . . . . .
H14A H 0.3844 1.0945 0.5606 0.076 Uiso 1 1 calc R U . . .
H14B H 0.4044 0.8932 0.5674 0.076 Uiso 1 1 calc R U . . .
C16 C 0.24347(16) 0.9901(3) 0.62499(12) 0.0652(6) Uani 1 1 d . . . . .
H16 H 0.2848 1.0332 0.6587 0.078 Uiso 1 1 calc R U . . .
C17 C 0.15719(17) 0.9715(3) 0.64081(12) 0.0707(7) Uani 1 1 d . . . . .
H17 H 0.1404 1.0008 0.6849 0.085 Uiso 1 1 calc R U . . .
N1 N 0.33424(9) 0.8127(2) 0.43843(8) 0.0430(4) Uani 1 1 d . . . . .
O1 O 0.12873(10) 0.49291(18) 0.47830(8) 0.0637(4) Uani 1 1 d . . . . .
O3 O 0.08805(9) 0.5315(2) 0.33222(8) 0.0740(5) Uani 1 1 d . . . . .
O4 O 0.07550(10) 0.8180(2) 0.35168(9) 0.0826(5) Uani 1 1 d . . . . .
O2 O 0.26446(11) 0.4055(3) 0.45825(13) 0.1114(8) Uani 1 1 d . . . . .
C26 C 0.1190(2) 0.3480(3) 0.52582(15) 0.0922(9) Uani 1 1 d . . . . .
H26A H 0.1176 0.2396 0.5004 0.138 Uiso 1 1 calc R U . . .
H26B H 0.0647 0.3613 0.5485 0.138 Uiso 1 1 calc R U . . .
H26C H 0.1682 0.3470 0.5601 0.138 Uiso 1 1 calc R U . . .
C25 C 0.00046(16) 0.5301(5) 0.29634(15) 0.1026(11) Uani 1 1 d . . . . .
H25A H -0.0411 0.5846 0.3251 0.154 Uiso 1 1 calc R U . . .
H25B H -0.0174 0.4112 0.2868 0.154 Uiso 1 1 calc R U . . .
H25C H 0.0019 0.5936 0.2534 0.154 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
C5 C6 C1 118.76(17) . . ?
C5 C6 C7 118.76(16) . . ?
C1 C6 C7 122.48(18) . . ?
C6 C5 C8 118.50(17) . . ?
C6 C5 C4 118.67(18) . . ?
C8 C5 C4 122.83(19) . . ?
C7 C10 C9 118.77(17) . . ?
C7 C10 C11 120.68(16) . . ?
C9 C10 C11 120.54(16) . . ?
N1 C21 C20 111.18(15) . . ?
N1 C21 C22 101.22(13) . . ?
C20 C21 C22 121.53(15) . . ?
C10 C7 C6 121.71(17) . . ?
N1 C11 C10 113.67(15) . . ?
N1 C11 C12 102.57(14) . . ?
C10 C11 C12 113.59(16) . . ?
C23 C22 C24 110.28(16) . . ?
C23 C22 C12 109.22(15) . . ?
C24 C22 C12 110.21(16) . . ?
C23 C22 C21 112.88(16) . . ?
C24 C22 C21 111.96(15) . . ?
C12 C22 C21 101.96(14) . . ?
C15 C20 C19 118.62(17) . . ?
C15 C20 C21 119.65(16) . . ?
C19 C20 C21 121.54(17) . . ?
C16 C15 C20 119.05(19) . . ?
C16 C15 C14 119.62(18) . . ?
C20 C15 C14 121.30(17) . . ?
C2 C1 C6 121.0(2) . . ?
C8 C9 C10 121.00(18) . . ?
C9 C8 C5 121.25(18) . . ?
C1 C2 C3 120.3(2) . . ?
O4 C23 O3 123.35(18) . . ?
O4 C23 C22 126.00(19) . . ?
O3 C23 C22 110.60(18) . . ?
O2 C24 O1 123.7(2) . . ?
O2 C24 C22 124.4(2) . . ?
O1 C24 C22 111.82(16) . . ?
N1 C13 C14 108.12(17) . . ?
C3 C4 C5 120.5(2) . . ?
C18 C19 C20 120.9(2) . . ?
C11 C12 C22 105.99(15) . . ?
C17 C18 C19 119.9(2) . . ?
C4 C3 C2 120.7(2) . . ?
C13 C14 C15 112.59(17) . . ?
C17 C16 C15 121.7(2) . . ?
C16 C17 C18 119.7(2) . . ?
C11 N1 C21 104.99(14) . . ?
C11 N1 C13 114.90(15) . . ?
C21 N1 C13 110.79(14) . . ?
C24 O1 C26 117.33(19) . . ?
C23 O3 C25 116.6(2) . . ?
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
C6 C5 1.414(3) . ?
C6 C1 1.417(3) . ?
C6 C7 1.422(2) . ?
C5 C8 1.415(3) . ?
C5 C4 1.419(3) . ?
C10 C7 1.368(2) . ?
C10 C9 1.415(3) . ?
C10 C11 1.510(2) . ?
C21 N1 1.461(2) . ?
C21 C20 1.513(2) . ?
C21 C22 1.557(2) . ?
C11 N1 1.460(2) . ?
C11 C12 1.536(3) . ?
C22 C23 1.519(3) . ?
C22 C24 1.526(3) . ?
C22 C12 1.557(3) . ?
C20 C15 1.397(3) . ?
C20 C19 1.398(3) . ?
C15 C16 1.395(3) . ?
C15 C14 1.514(3) . ?
C1 C2 1.356(3) . ?
C9 C8 1.359(3) . ?
C2 C3 1.396(3) . ?
C23 O4 1.195(2) . ?
C23 O3 1.333(3) . ?
C24 O2 1.184(2) . ?
C24 O1 1.325(2) . ?
C13 N1 1.466(2) . ?
C13 C14 1.506(3) . ?
C4 C3 1.364(3) . ?
C19 C18 1.386(3) . ?
C18 C17 1.378(3) . ?
C16 C17 1.365(3) . ?
O1 C26 1.448(3) . ?
O3 C25 1.450(3) . ?
