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#$Date: 2022-05-05 00:53:50 +0300 (Thu, 05 May 2022) $
#$Revision: 274890 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/00/7130047.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_7130047
loop_
_publ_author_name
'Nunewar, Saiprasad'
'Kumar, Sanjeev'
'Priyanka, Pendam'
'Girase, Pradeep'
'Kanchupalli, Vinaykumar'
_publ_section_title
;
 The solvent-controlled Rh(iii)-catalyzed switchable [4+2] annulation of
 2-arylIndoles with iodonium ylides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01386J
_journal_year                    2022
_chemical_formula_moiety         'C21 H17 N O2'
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-01
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2022-03-07 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.836(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1663(15)
_cell_length_b                   20.190(7)
_cell_length_c                   14.945(5)
_cell_measurement_reflns_used    9188
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.64
_cell_measurement_theta_min      2.44
_cell_volume                     1547.8(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      296.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0565
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19188
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.440
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1274 before and 0.0844 after correction. The Ratio of minimum to maximum transmission is 0.8625. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.213
_refine_ls_abs_structure_details
;
 Flack x determined using 1263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.285
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2695
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.285
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0937
_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)+(0.1386P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1830
_refine_ls_wR_factor_ref         0.1845
_reflns_Friedel_coverage         0.980
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2601
_reflns_number_total             2695
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc01386j2.cif
_cod_data_source_block           exter014_0m
_cod_original_cell_volume        1547.8(8)
_cod_database_code               7130047
_shelx_shelxl_version_number     2018/3
_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   0.991
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C17(H17), C4(H4), C5(H5), C19(H19), C20(H20), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0979(6) 0.64905(14) 0.4754(2) 0.0613(8) Uani 1 1 d . . . . .
N1 N 0.8348(6) 0.45394(16) 0.6441(2) 0.0486(8) Uani 1 1 d . . . . .
H1 H 0.867270 0.486223 0.681294 0.058 Uiso 1 1 calc R . . . .
O2 O -0.0435(8) 0.45780(18) 0.2985(2) 0.0785(11) Uani 1 1 d . . . . .
C17 C 0.0800(7) 0.54110(19) 0.4460(3) 0.0448(9) Uani 1 1 d . . . . .
H17 H -0.044912 0.534480 0.396641 0.054 Uiso 1 1 calc R . . . .
C7 C 0.6458(6) 0.39258(18) 0.5283(2) 0.0398(8) Uani 1 1 d . . . . .
C9 C 0.4538(7) 0.50319(18) 0.5475(2) 0.0407(8) Uani 1 1 d . . . . .
C11 C 0.2828(7) 0.42949(18) 0.4206(2) 0.0400(8) Uani 1 1 d . . . . .
C13 C 0.4846(9) 0.3159(2) 0.4029(3) 0.0488(9) Uani 1 1 d . . . . .
H13A H 0.391301 0.282424 0.432876 0.059 Uiso 1 1 calc R . . . .
H13B H 0.666164 0.302587 0.407287 0.059 Uiso 1 1 calc R . . . .
C4 C 1.1819(9) 0.2722(2) 0.6248(3) 0.0598(11) Uani 1 1 d . . . . .
H4 H 1.255042 0.230675 0.618227 0.072 Uiso 1 1 calc R . . . .
C5 C 0.9652(8) 0.29143(19) 0.5665(3) 0.0511(9) Uani 1 1 d . . . . .
H5 H 0.891849 0.262606 0.522015 0.061 Uiso 1 1 calc R . . . .
C14 C 0.3740(10) 0.3188(2) 0.3042(3) 0.0590(11) Uani 1 1 d . . . . .
H14A H 0.486557 0.345532 0.271156 0.071 Uiso 1 1 calc R . . . .
H14B H 0.365931 0.274589 0.278782 0.071 Uiso 1 1 calc R . . . .
C15 C 0.1068(9) 0.3484(2) 0.2957(3) 0.0602(11) Uani 1 1 d . . . . .
H15A H -0.007175 0.319762 0.325381 0.072 Uiso 1 1 calc R . . . .
H15B H 0.038688 0.350784 0.232383 0.072 Uiso 1 1 calc R . . . .
C10 C 0.2698(6) 0.49159(19) 0.4701(2) 0.0400(8) Uani 1 1 d . . . . .
C12 C 0.4654(7) 0.38132(17) 0.4505(2) 0.0389(8) Uani 1 1 d . . . . .
C19 C 0.2646(8) 0.6106(2) 0.5695(3) 0.0526(10) Uani 1 1 d . . . . .
H19 H 0.264127 0.650356 0.600853 0.063 Uiso 1 1 calc R . . . .
C18 C 0.0783(8) 0.59899(19) 0.4949(3) 0.0472(9) Uani 1 1 d . . . . .
C16 C 0.1045(8) 0.41713(19) 0.3364(3) 0.0468(9) Uani 1 1 d . . . . .
C8 C 0.6407(7) 0.45319(17) 0.5744(2) 0.0413(8) Uani 1 1 d . . . . .
C6 C 0.8575(7) 0.35474(18) 0.5753(3) 0.0427(8) Uani 1 1 d . . . . .
C20 C 0.4470(8) 0.5632(2) 0.5958(3) 0.0510(10) Uani 1 1 d . . . . .
H20 H 0.567820 0.570492 0.646075 0.061 Uiso 1 1 calc R . . . .
C3 C 1.2915(9) 0.3145(3) 0.6930(3) 0.0614(11) Uani 1 1 d . . . . .
H3 H 1.437079 0.300594 0.731050 0.074 Uiso 1 1 calc R . . . .
C21 C -0.2933(10) 0.6398(2) 0.4009(3) 0.0622(11) Uani 1 1 d . . . . .
H21A H -0.212413 0.635279 0.346669 0.093 Uiso 1 1 calc GR . . . .
H21B H -0.407837 0.677449 0.395712 0.093 Uiso 1 1 calc GR . . . .
H21C H -0.391566 0.600591 0.410193 0.093 Uiso 1 1 calc GR . . . .
C2 C 1.1894(9) 0.3756(2) 0.7051(3) 0.0576(10) Uani 1 1 d . . . . .
H2 H 1.262260 0.403391 0.750926 0.069 Uiso 1 1 calc R . . . .
C1 C 0.9720(7) 0.3954(2) 0.6465(3) 0.0458(8) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O1 C21 117.5(3) . . ?
C8 N1 C1 110.0(3) . . ?
C18 C17 C10 120.8(4) . . ?
C12 C7 C6 134.3(3) . . ?
C8 C7 C12 119.5(3) . . ?
C8 C7 C6 106.2(3) . . ?
C8 C9 C10 118.5(3) . . ?
C20 C9 C10 120.0(3) . . ?
C20 C9 C8 121.4(4) . . ?
C10 C11 C16 120.7(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 C16 118.8(3) . . ?
C12 C13 C14 112.6(3) . . ?
C5 C4 C3 120.9(4) . . ?
C4 C5 C6 119.6(4) . . ?
C15 C14 C13 109.6(4) . . ?
C14 C15 C16 112.5(4) . . ?
C17 C10 C9 117.7(3) . . ?
C17 C10 C11 123.3(3) . . ?
C9 C10 C11 119.0(3) . . ?
C7 C12 C13 116.9(3) . . ?
C11 C12 C7 120.4(3) . . ?
C11 C12 C13 122.7(3) . . ?
C20 C19 C18 119.7(4) . . ?
O1 C18 C17 124.0(4) . . ?
O1 C18 C19 115.0(3) . . ?
C17 C18 C19 121.0(4) . . ?
O2 C16 C11 124.9(4) . . ?
O2 C16 C15 117.7(4) . . ?
C11 C16 C15 117.3(4) . . ?
N1 C8 C7 109.3(3) . . ?
N1 C8 C9 128.6(3) . . ?
C7 C8 C9 122.1(4) . . ?
C5 C6 C7 136.0(4) . . ?
C5 C6 C1 117.5(4) . . ?
C1 C6 C7 106.5(3) . . ?
C19 C20 C9 120.8(4) . . ?
C2 C3 C4 121.3(4) . . ?
C3 C2 C1 118.1(5) . . ?
N1 C1 C6 108.1(3) . . ?
N1 C1 C2 129.4(4) . . ?
C2 C1 C6 122.6(4) . . ?
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 C18 1.368(5) . ?
O1 C21 1.422(7) . ?
N1 C8 1.357(5) . ?
N1 C1 1.377(5) . ?
O2 C16 1.215(5) . ?
C17 C10 1.416(5) . ?
C17 C18 1.379(5) . ?
C7 C12 1.418(5) . ?
C7 C8 1.406(5) . ?
C7 C6 1.446(5) . ?
C9 C10 1.427(5) . ?
C9 C8 1.422(5) . ?
C9 C20 1.412(5) . ?
C11 C10 1.461(5) . ?
C11 C12 1.391(5) . ?
C11 C16 1.489(5) . ?
C13 C14 1.517(6) . ?
C13 C12 1.510(5) . ?
C4 C5 1.389(6) . ?
C4 C3 1.397(7) . ?
C5 C6 1.407(5) . ?
C14 C15 1.496(7) . ?
C15 C16 1.516(6) . ?
C19 C18 1.403(6) . ?
C19 C20 1.368(6) . ?
C6 C1 1.416(6) . ?
C3 C2 1.363(7) . ?
C2 C1 1.397(6) . ?
