#------------------------------------------------------------------------------
#$Date: 2022-01-07 00:55:01 +0200 (Fri, 07 Jan 2022) $
#$Revision: 271890 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/95/7129511.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_7129511
loop_
_publ_author_name
'Dey, Arnab'
'Singh, Anurag'
'Volla, Chandra M. R.'
_publ_section_title
;
 Cobalt-catalyzed highly diastereoselective [3 + 2] carboannulation
 reactions: facile access to substituted indane derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05245D
_journal_year                    2022
_chemical_formula_moiety         'C24 H21 N3 O'
_chemical_formula_sum            'C24 H21 N3 O'
_chemical_formula_weight         367.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-05
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-01-31 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                100.465(5)
_cell_angle_beta                 110.413(5)
_cell_angle_gamma                103.140(5)
_cell_formula_units_Z            2
_cell_length_a                   9.3029(5)
_cell_length_b                   9.8555(6)
_cell_length_c                   11.3680(6)
_cell_measurement_reflns_used    4238
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.7760
_cell_measurement_theta_min      2.4460
_cell_volume                     911.54(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  19.00   0.50    8.00    --  -20.00 -72.00 -36.00  258
  2  ω   -110.00  16.00   0.50    8.00    --  -20.00   0.00 -36.00  252
  3  ω    -78.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  194
  4  ω    -35.00   2.00   0.50    8.00    --  -20.00 -72.00-180.00   74
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0055672000
_diffrn_orient_matrix_UB_12      0.0247648000
_diffrn_orient_matrix_UB_13      0.0603340000
_diffrn_orient_matrix_UB_21      0.0854301000
_diffrn_orient_matrix_UB_22      0.0230066000
_diffrn_orient_matrix_UB_23      0.0327610000
_diffrn_orient_matrix_UB_31      0.0036654000
_diffrn_orient_matrix_UB_32      0.0692818000
_diffrn_orient_matrix_UB_33      -0.0103464000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.998
_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       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6804
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.995
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0492
_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)+(0.0965P)²+0.1235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2525
_reflns_number_total             3206
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc05245d2.cif
_cod_data_source_block           cmrv-ad-662_mo
_cod_database_code               7129511
_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.
;
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.983
_reflns_odcompleteness_completeness 88.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.05
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C24(H24), C16(H16), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C4(H4), C1(H1), C22(H22), C11(H11), C21(H21), C3(H3),
 C19(H19), C20(H20), C2(H2)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.630
_oxdiff_exptl_absorpt_empirical_full_min 0.817
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.09190(19) 0.61164(17) 0.35402(15) 0.0292(4) Uani 1 1 d . . . . .
N3 N 0.4978(2) 0.67831(19) 0.73673(17) 0.0234(5) Uani 1 1 d . . . . .
N2 N 0.5170(2) 0.76773(19) 0.83739(17) 0.0241(5) Uani 1 1 d . . . . .
N1 N 0.7895(3) 0.7503(2) 0.92748(19) 0.0318(5) Uani 1 1 d . . . . .
C13 C 0.2091(3) 0.2529(2) 0.4098(2) 0.0257(5) Uani 1 1 d . . . . .
H13 H 0.1949 0.2145 0.3222 0.031 Uiso 1 1 calc R . . . .
C15 C 0.3059(3) 0.5158(2) 0.4048(2) 0.0209(5) Uani 1 1 d . . . . .
H15 H 0.3983 0.5072 0.3815 0.025 Uiso 1 1 calc R . . . .
C14 C 0.2589(3) 0.4012(2) 0.4662(2) 0.0207(5) Uani 1 1 d . . . . .
C6 C 0.3298(3) 0.6253(2) 0.6321(2) 0.0220(5) Uani 1 1 d . . . . .
C12 C 0.1803(3) 0.1613(2) 0.4840(2) 0.0295(6) Uani 1 1 d . . . . .
H12 H 0.1432 0.0590 0.4462 0.035 Uiso 1 1 calc R . . . .
C4 C 0.7127(3) 0.9351(2) 1.0374(2) 0.0239(5) Uani 1 1 d . . . . .
H4 H 0.6319 0.9784 1.0397 0.029 Uiso 1 1 calc R . . . .
C9 C 0.2563(3) 0.3682(2) 0.6720(2) 0.0251(5) Uani 1 1 d . . . . .
C5 C 0.6811(3) 0.8183(2) 0.9364(2) 0.0218(5) Uani 1 1 d . . . . .
C8 C 0.2789(3) 0.4592(2) 0.5944(2) 0.0210(5) Uani 1 1 d . . . . .
C7 C 0.2098(3) 0.6869(2) 0.6691(2) 0.0280(6) Uani 1 1 d . . . . .
H7A H 0.1991 0.6563 0.7438 0.042 Uiso 1 1 calc GR . . . .
H7B H 0.1044 0.6505 0.5944 0.042 Uiso 1 1 calc GR . . . .
H7C H 0.2491 0.7933 0.6928 0.042 Uiso 1 1 calc GR . . . .
C24 C 0.1660(3) 0.5294(2) 0.2880(2) 0.0257(5) Uani 1 1 d . . . . .
H24 H 0.0911 0.4353 0.2216 0.031 Uiso 1 1 calc R . . . .
C1 C 0.9381(3) 0.8039(3) 1.0265(2) 0.0310(6) Uani 1 1 d . . . . .
H1 H 1.0169 0.7582 1.0240 0.037 Uiso 1 1 calc R . . . .
C23 C 0.2447(3) 0.6400(2) 0.2344(2) 0.0253(5) Uani 1 1 d . . . . .
C16 C 0.3528(3) 0.6634(2) 0.5099(2) 0.0221(5) Uani 1 1 d . . . . .
H16 H 0.4674 0.7220 0.5351 0.026 Uiso 1 1 calc R . . . .
C22 C 0.2844(3) 0.6312(3) 0.1277(2) 0.0307(6) Uani 1 1 d . . . . .
H22 H 0.2542 0.5406 0.0647 0.037 Uiso 1 1 calc R . . . .
C11 C 0.2055(3) 0.2185(2) 0.6131(2) 0.0297(6) Uani 1 1 d . . . . .
H11 H 0.1875 0.1539 0.6629 0.036 Uiso 1 1 calc R . . . .
C21 C 0.3701(3) 0.7592(3) 0.1155(2) 0.0345(6) Uani 1 1 d . . . . .
H21 H 0.3958 0.7564 0.0414 0.041 Uiso 1 1 calc R . . . .
C10 C 0.2853(3) 0.4222(3) 0.8136(2) 0.0315(6) Uani 1 1 d . . . . .
H10A H 0.3841 0.5059 0.8584 0.047 Uiso 1 1 calc GR . . . .
H10B H 0.2974 0.3445 0.8555 0.047 Uiso 1 1 calc GR . . . .
H10C H 0.1934 0.4515 0.8190 0.047 Uiso 1 1 calc GR . . . .
C18 C 0.2919(3) 0.7729(2) 0.3283(2) 0.0269(6) Uani 1 1 d . . . . .
C3 C 0.8654(3) 0.9877(3) 1.1356(2) 0.0334(6) Uani 1 1 d . . . . .
H3 H 0.8922 1.0697 1.2070 0.040 Uiso 1 1 calc R . . . .
C19 C 0.3805(3) 0.8988(3) 0.3172(2) 0.0326(6) Uani 1 1 d . . . . .
H19 H 0.4147 0.9890 0.3820 0.039 Uiso 1 1 calc R . . . .
C17 C 0.2353(3) 0.7354(2) 0.4315(2) 0.0263(5) Uani 1 1 d . . . . .
H17 H 0.2185 0.8171 0.4859 0.032 Uiso 1 1 calc R . . . .
C20 C 0.4185(3) 0.8905(3) 0.2090(2) 0.0353(6) Uani 1 1 d . . . . .
H20 H 0.4786 0.9762 0.1991 0.042 Uiso 1 1 calc R . . . .
C2 C 0.9794(3) 0.9225(3) 1.1311(2) 0.0318(6) Uani 1 1 d . . . . .
H2 H 1.0853 0.9585 1.1989 0.038 Uiso 1 1 calc R . . . .
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
C24 O1 C17 96.64(16) . . ?
N2 N3 C6 114.46(18) . . ?
N3 N2 C5 113.29(18) . . ?
C1 N1 C5 116.5(2) . . ?
C14 C13 H13 120.7 . . ?
C14 C13 C12 118.5(2) . . ?
C12 C13 H13 120.7 . . ?
C14 C15 H15 111.4 . . ?
C14 C15 C24 115.66(18) . . ?
C14 C15 C16 105.00(16) . . ?
C24 C15 H15 111.4 . . ?
C24 C15 C16 101.32(17) . . ?
C16 C15 H15 111.4 . . ?
C13 C14 C15 125.98(19) . . ?
C13 C14 C8 121.42(19) . . ?
C8 C14 C15 112.51(18) . . ?
N3 C6 C8 106.31(17) . . ?
N3 C6 C7 114.53(17) . . ?
N3 C6 C16 103.78(16) . . ?
C8 C6 C16 103.94(16) . . ?
C7 C6 C8 113.20(18) . . ?
C7 C6 C16 114.01(18) . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C5 C4 H4 121.3 . . ?
C5 C4 C3 117.5(2) . . ?
C3 C4 H4 121.3 . . ?
C8 C9 C10 124.0(2) . . ?
C11 C9 C8 117.0(2) . . ?
C11 C9 C10 119.0(2) . . ?
N1 C5 N2 121.16(19) . . ?
N1 C5 C4 124.4(2) . . ?
C4 C5 N2 114.4(2) . . ?
C14 C8 C6 111.25(18) . . ?
C14 C8 C9 120.6(2) . . ?
C9 C8 C6 128.12(19) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C24 C15 102.05(16) . . ?
O1 C24 H24 115.2 . . ?
O1 C24 C23 101.59(17) . . ?
C15 C24 H24 115.2 . . ?
C23 C24 C15 105.87(18) . . ?
C23 C24 H24 115.2 . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.4(2) . . ?
C2 C1 H1 118.8 . . ?
C22 C23 C24 134.3(2) . . ?
C22 C23 C18 121.0(2) . . ?
C18 C23 C24 104.47(19) . . ?
C15 C16 C6 107.07(17) . . ?
C15 C16 H16 110.5 . . ?
C6 C16 H16 110.5 . . ?
C17 C16 C15 100.79(17) . . ?
C17 C16 C6 117.00(18) . . ?
C17 C16 H16 110.5 . . ?
C23 C22 H22 121.1 . . ?
C23 C22 C21 117.8(2) . . ?
C21 C22 H22 121.1 . . ?
C12 C11 C9 122.0(2) . . ?
C12 C11 H11 119.0 . . ?
C9 C11 H11 119.0 . . ?
C22 C21 H21 119.4 . . ?
C20 C21 C22 121.2(2) . . ?
C20 C21 H21 119.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C23 C18 C17 104.75(19) . . ?
C19 C18 C23 120.8(2) . . ?
C19 C18 C17 134.3(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.9 . . ?
C18 C19 H19 120.9 . . ?
C18 C19 C20 118.2(2) . . ?
C20 C19 H19 120.9 . . ?
O1 C17 C16 101.74(17) . . ?
O1 C17 C18 101.76(17) . . ?
O1 C17 H17 115.0 . . ?
C16 C17 H17 115.0 . . ?
C18 C17 C16 106.56(18) . . ?
C18 C17 H17 115.0 . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.5 . . ?
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
O1 C24 1.446(3) . ?
O1 C17 1.447(3) . ?
N3 N2 1.240(2) . ?
N3 C6 1.496(3) . ?
N2 C5 1.448(3) . ?
N1 C5 1.353(3) . ?
N1 C1 1.350(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(3) . ?
C13 C12 1.385(3) . ?
C15 H15 1.0000 . ?
C15 C14 1.494(3) . ?
C15 C24 1.553(3) . ?
C15 C16 1.565(3) . ?
C14 C8 1.395(3) . ?
C6 C8 1.529(3) . ?
C6 C7 1.527(3) . ?
C6 C16 1.573(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.364(3) . ?
C4 C3 1.372(3) . ?
C9 C8 1.400(3) . ?
C9 C11 1.397(3) . ?
C9 C10 1.506(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C24 H24 1.0000 . ?
C24 C23 1.511(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.378(3) . ?
C23 C22 1.380(3) . ?
C23 C18 1.397(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.548(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.389(3) . ?
C11 H11 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.382(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C18 C19 1.378(3) . ?
C18 C17 1.514(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.370(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(3) . ?
C17 H17 1.0000 . ?
C20 H20 0.9500 . ?
C2 H2 0.9500 . ?
