#------------------------------------------------------------------------------
#$Date: 2019-11-04 11:38:04 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222623 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/40/4034063.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_4034063
loop_
_publ_author_name
'Lv, Ningning'
'Chen, Zhengkai'
'Liu, Zhanxiang'
'Zhang, Yuhong'
_publ_section_title
;
 Redox-Neutral Rhodium(III)-Catalyzed Annulation of Arylhydrazines with
 Sulfoxonium Ylides To Synthesize 2-Arylindoles.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13013
_journal_page_last               13021
_journal_paper_doi               10.1021/acs.joc.9b01815
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.5770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3951(2)
_cell_length_b                   9.1572(2)
_cell_length_c                   14.1320(3)
_cell_measurement_reflns_used    5185
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.68
_cell_volume                     1301.92(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170.01
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0334
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11719
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.271
_diffrn_reflns_theta_min         2.677
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0740 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.8923.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0435
_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)+(0.0447P)²+0.4023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1127
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2549
_reflns_number_total             3221
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b01815_si_002.cif
_cod_data_source_block           181115_lnn_l_088_7_0m_a
_cod_database_code               4034063
_shelx_shelxl_version_number     2016/6
_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   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C7(H7), C10(H10), C11(H11), C12(H12),
  C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.84521(10) 0.63795(11) 0.27620(8) 0.0418(3) Uani 1 1 d .
N1 N 0.60940(10) 0.49634(12) 0.26018(8) 0.0307(2) Uani 1 1 d .
N2 N 0.71949(10) 0.43462(12) 0.23751(8) 0.0303(2) Uani 1 1 d .
H2 H 0.715981 0.343530 0.217169 0.036 Uiso 1 1 calc R
C1 C 0.28861(13) 0.65735(16) 0.17953(10) 0.0367(3) Uani 1 1 d .
H1 H 0.213923 0.671721 0.205769 0.044 Uiso 1 1 calc R
C2 C 0.28848(14) 0.71009(16) 0.08798(11) 0.0403(3) Uani 1 1 d .
H2A H 0.212587 0.760827 0.051135 0.048 Uiso 1 1 calc R
C3 C 0.39797(14) 0.69035(16) 0.04825(10) 0.0394(3) Uani 1 1 d .
H3 H 0.394060 0.726223 -0.015491 0.047 Uiso 1 1 calc R
C4 C 0.51150(14) 0.61975(15) 0.09993(10) 0.0352(3) Uani 1 1 d .
H4 H 0.586510 0.607587 0.073749 0.042 Uiso 1 1 calc R
C5 C 0.51059(12) 0.56750(14) 0.19192(9) 0.0291(3) Uani 1 1 d .
C6 C 0.40099(12) 0.58219(14) 0.23307(9) 0.0303(3) Uani 1 1 d .
C7 C 0.43628(13) 0.51180(15) 0.32679(9) 0.0328(3) Uani 1 1 d .
H7 H 0.381275 0.503268 0.370969 0.039 Uiso 1 1 calc R
C8 C 0.56274(12) 0.45920(14) 0.34139(9) 0.0302(3) Uani 1 1 d .
C9 C 0.64826(13) 0.38351(15) 0.42563(9) 0.0319(3) Uani 1 1 d .
C10 C 0.77530(14) 0.43625(17) 0.46883(10) 0.0374(3) Uani 1 1 d .
H10 H 0.807663 0.519576 0.442066 0.045 Uiso 1 1 calc R
C11 C 0.85465(16) 0.3684(2) 0.55027(11) 0.0483(4) Uani 1 1 d .
H11 H 0.940531 0.406210 0.579603 0.058 Uiso 1 1 calc R
C12 C 0.80989(18) 0.2467(2) 0.58892(12) 0.0550(5) Uani 1 1 d .
H12 H 0.865034 0.199768 0.644463 0.066 Uiso 1 1 calc R
C13 C 0.68462(19) 0.19259(19) 0.54689(12) 0.0543(4) Uani 1 1 d .
H13 H 0.653584 0.108556 0.573799 0.065 Uiso 1 1 calc R
C14 C 0.60368(15) 0.26027(16) 0.46552(11) 0.0421(3) Uani 1 1 d .
H14 H 0.517586 0.222353 0.436973 0.051 Uiso 1 1 calc R
C15 C 0.83227(12) 0.51250(14) 0.24623(9) 0.0314(3) Uani 1 1 d .
C16 C 0.93993(15) 0.43105(17) 0.21517(12) 0.0455(4) Uani 1 1 d .
H16A H 0.972113 0.489957 0.167957 0.068 Uiso 1 1 calc GR
H16B H 0.904527 0.338375 0.184792 0.068 Uiso 1 1 calc GR
H16C H 1.013502 0.411591 0.272454 0.068 Uiso 1 1 calc GR
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
N2 N1 C8 124.71(11)
C5 N1 N2 122.90(10)
C5 N1 C8 109.74(10)
N1 N2 H2 119.6
C15 N2 N1 120.81(11)
C15 N2 H2 119.6
C2 C1 H1 120.6
C2 C1 C6 118.79(13)
C6 C1 H1 120.6
C1 C2 H2A 119.3
C1 C2 C3 121.38(13)
C3 C2 H2A 119.3
C2 C3 H3 119.3
C4 C3 C2 121.33(13)
C4 C3 H3 119.3
C3 C4 H4 121.6
C3 C4 C5 116.75(12)
C5 C4 H4 121.6
N1 C5 C4 129.59(12)
N1 C5 C6 107.02(11)
C4 C5 C6 123.39(12)
C1 C6 C5 118.31(12)
C1 C6 C7 134.68(12)
C5 C6 C7 107.00(11)
C6 C7 H7 126.0
C8 C7 C6 108.08(11)
C8 C7 H7 126.0
N1 C8 C9 121.13(11)
C7 C8 N1 108.07(11)
C7 C8 C9 130.71(12)
C10 C9 C8 120.33(12)
C14 C9 C8 121.05(12)
C14 C9 C10 118.60(13)
C9 C10 H10 119.7
C11 C10 C9 120.63(15)
C11 C10 H10 119.7
C10 C11 H11 119.8
C12 C11 C10 120.33(16)
C12 C11 H11 119.8
C11 C12 H12 120.1
C11 C12 C13 119.84(15)
C13 C12 H12 120.1
C12 C13 H13 119.8
C12 C13 C14 120.39(16)
C14 C13 H13 119.8
C9 C14 H14 119.9
C13 C14 C9 120.21(15)
C13 C14 H14 119.9
O1 C15 N2 123.10(12)
O1 C15 C16 123.01(13)
N2 C15 C16 113.89(12)
C15 C16 H16A 109.5
C15 C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16B 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C15 1.2200(16)
N1 N2 1.3844(14)
N1 C5 1.3826(16)
N1 C8 1.3957(16)
N2 H2 0.8800
N2 C15 1.3511(16)
C1 H1 0.9500
C1 C2 1.381(2)
C1 C6 1.4021(19)
C2 H2A 0.9500
C2 C3 1.402(2)
C3 H3 0.9500
C3 C4 1.3822(19)
C4 H4 0.9500
C4 C5 1.3874(18)
C5 C6 1.4099(18)
C6 C7 1.4352(18)
C7 H7 0.9500
C7 C8 1.3661(18)
C8 C9 1.4681(18)
C9 C10 1.3942(19)
C9 C14 1.392(2)
C10 H10 0.9500
C10 C11 1.383(2)
C11 H11 0.9500
C11 C12 1.373(3)
C12 H12 0.9500
C12 C13 1.380(3)
C13 H13 0.9500
C13 C14 1.388(2)
C14 H14 0.9500
C15 C16 1.4996(19)
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
