#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:25:05 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273430 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158514.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_7158514
loop_
_publ_author_name
'Suleman, Muhammad'
'Qi, Minghui'
'Xie, Jianwei'
'Lu, Ping'
'Wang, Yanguang'
_publ_section_title
;
 Rh(III)-Catalyzed C-H bond activation/annulation reactions of arylacyl
 ammonium salts with 4-diazoisochroman-3-imines and
 4-diazoisoquinolin-3-ones.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1900
_journal_page_last               1906
_journal_paper_doi               10.1039/d1ob02405a
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H12 O3'
_chemical_formula_sum            'C17 H12 O3'
_chemical_formula_weight         264.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-10 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.872(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.849(4)
_cell_length_b                   8.586(3)
_cell_length_c                   12.730(5)
_cell_measurement_reflns_used    6661
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.87
_cell_volume                     1290.4(8)
_computing_cell_refinement       SAINT
_computing.data_collection       Bruker
_computing.data_reduction        SAINT
_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      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12035
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.016
_diffrn_reflns_theta_min         2.255
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.3769
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1633 before and 0.0897 after correction.
The Ratio of minimum to maximum transmission is 0.5056.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.968
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.186
_refine_ls_abs_structure_details
;
 Flack x determined using 1852 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5216
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0791
_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)+(0.1253P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.1783
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.861
_reflns_Friedel_fraction_max     0.841
_reflns_number_gt                4868
_reflns_number_total             5216
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02405a2.cif
_cod_data_source_block           200723_ms586_004_2_0m
_cod_depositor_comments
'Adding full bibliography for 7158513--7158514.cif.'
_cod_original_cell_volume        1290.3(8)
_cod_database_code               7158514
_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   0.962
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C25(H25A,H25B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C31(H31), C32(H32), C33(H33), C34(H34)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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 -0.5245(2) 1.2279(4) 0.8172(3) 0.0521(8) Uani 1 1 d . . . . .
O2 O -0.2549(2) 1.1034(3) 0.56628(19) 0.0431(7) Uani 1 1 d . . . . .
O3 O -0.1571(2) 1.3204(3) 0.58631(18) 0.0368(6) Uani 1 1 d . . . . .
C1 C -0.4213(3) 0.9052(5) 0.8523(3) 0.0363(7) Uani 1 1 d . . . . .
H1 H -0.495546 0.905648 0.875044 0.044 Uiso 1 1 calc R . . . .
C2 C -0.3567(3) 0.7712(4) 0.8588(3) 0.0367(7) Uani 1 1 d . . . . .
H2 H -0.386149 0.678272 0.886403 0.044 Uiso 1 1 calc R . . . .
C3 C -0.2468(3) 0.7728(4) 0.8243(3) 0.0334(7) Uani 1 1 d . . . . .
H3 H -0.202663 0.680307 0.828654 0.040 Uiso 1 1 calc R . . . .
C4 C -0.2018(3) 0.9079(4) 0.7840(3) 0.0301(7) Uani 1 1 d . . . . .
H4 H -0.127878 0.907823 0.760410 0.036 Uiso 1 1 calc R . . . .
C5 C -0.2668(2) 1.0424(4) 0.7788(2) 0.0246(6) Uani 1 1 d . . . . .
C6 C -0.3757(2) 1.0395(4) 0.8117(2) 0.0279(6) Uani 1 1 d . . . . .
C7 C -0.4287(3) 1.1946(4) 0.7992(3) 0.0328(7) Uani 1 1 d . . . . .
C8 C -0.3418(3) 1.3064(4) 0.7596(3) 0.0340(7) Uani 1 1 d . . . . .
H8A H -0.323320 1.390051 0.811784 0.041 Uiso 1 1 calc R . . . .
H8B H -0.371280 1.354649 0.692103 0.041 Uiso 1 1 calc R . . . .
C9 C -0.2335(2) 1.2048(4) 0.7437(2) 0.0264(6) Uani 1 1 d . . . . .
C10 C -0.2159(3) 1.2038(4) 0.6250(2) 0.0299(7) Uani 1 1 d . . . . .
C11 C -0.1159(3) 1.4475(4) 0.6550(3) 0.0379(7) Uani 1 1 d . . . . .
H11A H -0.178724 1.520924 0.664180 0.045 Uiso 1 1 calc R . . . .
H11B H -0.055903 1.504881 0.621602 0.045 Uiso 1 1 calc R . . . .
C12 C -0.0691(3) 1.3887(4) 0.7615(3) 0.0319(7) Uani 1 1 d . . . . .
C13 C -0.1275(2) 1.2683(4) 0.8060(2) 0.0267(6) Uani 1 1 d . . . . .
C14 C -0.0884(3) 1.2113(4) 0.9051(2) 0.0317(7) Uani 1 1 d . . . . .
H14 H -0.128228 1.129871 0.936342 0.038 Uiso 1 1 calc R . . . .
C15 C 0.0090(3) 1.2736(5) 0.9585(3) 0.0369(7) Uani 1 1 d . . . . .
H15 H 0.034750 1.235462 1.026393 0.044 Uiso 1 1 calc R . . . .
C16 C 0.0681(3) 1.3909(5) 0.9125(3) 0.0388(8) Uani 1 1 d . . . . .
H16 H 0.135530 1.431277 0.948062 0.047 Uiso 1 1 calc R . . . .
C17 C 0.0285(3) 1.4498(4) 0.8139(3) 0.0376(8) Uani 1 1 d . . . . .
H17 H 0.068334 1.531477 0.782804 0.045 Uiso 1 1 calc R . . . .
O4 O 0.2554(3) 0.9948(4) 0.98943(19) 0.0484(7) Uani 1 1 d . . . . .
O5 O 0.03331(19) 0.8087(4) 0.6643(2) 0.0399(6) Uani 1 1 d . . . . .
O6 O 0.03886(19) 1.0441(3) 0.5971(2) 0.0390(6) Uani 1 1 d . . . . .
C18 C 0.3263(3) 0.6736(4) 0.9121(2) 0.0336(7) Uani 1 1 d . . . . .
H18 H 0.340480 0.677501 0.986636 0.040 Uiso 1 1 calc R . . . .
C19 C 0.3515(3) 0.5423(5) 0.8566(3) 0.0387(8) Uani 1 1 d . . . . .
H19 H 0.384083 0.454424 0.893057 0.046 Uiso 1 1 calc R . . . .
C20 C 0.3292(3) 0.5374(5) 0.7454(3) 0.0372(7) Uani 1 1 d . . . . .
H20 H 0.346755 0.445867 0.708148 0.045 Uiso 1 1 calc R . . . .
C21 C 0.2819(3) 0.6647(4) 0.6902(2) 0.0326(7) Uani 1 1 d . . . . .
H21 H 0.266700 0.660691 0.615761 0.039 Uiso 1 1 calc R . . . .
C22 C 0.2574(2) 0.7982(4) 0.7463(2) 0.0263(6) Uani 1 1 d . . . . .
C23 C 0.2792(2) 0.8014(4) 0.8556(2) 0.0279(6) Uani 1 1 d . . . . .
C24 C 0.2477(3) 0.9535(4) 0.8969(2) 0.0303(6) Uani 1 1 d . . . . .
C25 C 0.2029(3) 1.0551(4) 0.8042(2) 0.0310(6) Uani 1 1 d . . . . .
H25A H 0.250087 1.149649 0.799731 0.037 Uiso 1 1 calc R . . . .
H25B H 0.123795 1.087376 0.812043 0.037 Uiso 1 1 calc R . . . .
C26 C 0.2091(2) 0.9515(4) 0.7032(2) 0.0251(6) Uani 1 1 d . . . . .
C27 C 0.0872(2) 0.9251(4) 0.6531(2) 0.0291(6) Uani 1 1 d . . . . .
C28 C 0.1033(3) 1.1854(5) 0.5831(3) 0.0399(8) Uani 1 1 d . . . . .
H28A H 0.103000 1.250571 0.647269 0.048 Uiso 1 1 calc R . . . .
H28B H 0.066947 1.245674 0.523157 0.048 Uiso 1 1 calc R . . . .
C29 C 0.2234(3) 1.1491(4) 0.5626(3) 0.0343(7) Uani 1 1 d . . . . .
C30 C 0.2776(3) 1.0291(4) 0.6212(2) 0.0272(6) Uani 1 1 d . . . . .
C31 C 0.3881(3) 0.9894(5) 0.6045(3) 0.0366(8) Uani 1 1 d . . . . .
H31 H 0.425200 0.907820 0.644370 0.044 Uiso 1 1 calc R . . . .
C32 C 0.4448(3) 1.0689(6) 0.5294(3) 0.0476(9) Uani 1 1 d . . . . .
H32 H 0.520386 1.041363 0.517896 0.057 Uiso 1 1 calc R . . . .
C33 C 0.3908(4) 1.1887(6) 0.4713(4) 0.0561(12) Uani 1 1 d . . . . .
H33 H 0.429648 1.243343 0.420460 0.067 Uiso 1 1 calc R . . . .
C34 C 0.2800(4) 1.2284(5) 0.4876(3) 0.0479(9) Uani 1 1 d . . . . .
H34 H 0.242907 1.309791 0.447587 0.057 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'
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
C10 O3 C11 119.9(2) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.9(3) . . ?
C6 C1 H1 120.6 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 C9 128.2(3) . . ?
C6 C5 C9 112.0(3) . . ?
C1 C6 C7 127.8(3) . . ?
C5 C6 C1 121.8(3) . . ?
C5 C6 C7 110.4(3) . . ?
O1 C7 C6 126.2(3) . . ?
O1 C7 C8 125.7(3) . . ?
C6 C7 C8 108.1(3) . . ?
C7 C8 H8A 110.6 . . ?
C7 C8 H8B 110.6 . . ?
C7 C8 C9 105.8(3) . . ?
H8A C8 H8B 108.7 . . ?
C9 C8 H8A 110.6 . . ?
C9 C8 H8B 110.6 . . ?
C5 C9 C8 103.6(2) . . ?
C5 C9 C10 109.9(2) . . ?
C5 C9 C13 113.3(2) . . ?
C10 C9 C8 107.9(2) . . ?
C13 C9 C8 112.2(3) . . ?
C13 C9 C10 109.6(2) . . ?
O2 C10 O3 119.4(3) . . ?
O2 C10 C9 122.3(3) . . ?
O3 C10 C9 118.3(3) . . ?
O3 C11 H11A 109.3 . . ?
O3 C11 H11B 109.3 . . ?
O3 C11 C12 111.6(3) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C13 C12 C11 117.2(3) . . ?
C17 C12 C11 122.2(3) . . ?
C17 C12 C13 120.5(3) . . ?
C12 C13 C9 118.0(3) . . ?
C12 C13 C14 119.4(3) . . ?
C14 C13 C9 122.6(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 119.8(3) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C27 O6 C28 119.6(2) . . ?
C19 C18 H18 120.9 . . ?
C19 C18 C23 118.2(3) . . ?
C23 C18 H18 120.9 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.7 . . ?
C20 C21 C22 118.7(3) . . ?
C22 C21 H21 120.7 . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 C26 128.1(2) . . ?
C23 C22 C26 112.1(3) . . ?
C18 C23 C24 128.0(3) . . ?
C22 C23 C18 121.9(3) . . ?
C22 C23 C24 110.1(3) . . ?
O4 C24 C23 126.9(3) . . ?
O4 C24 C25 124.8(3) . . ?
C23 C24 C25 108.3(2) . . ?
C24 C25 H25A 110.6 . . ?
C24 C25 H25B 110.6 . . ?
C24 C25 C26 105.8(3) . . ?
H25A C25 H25B 108.7 . . ?
C26 C25 H25A 110.6 . . ?
C26 C25 H25B 110.6 . . ?
C22 C26 C25 103.8(2) . . ?
C22 C26 C27 109.4(3) . . ?
C22 C26 C30 114.7(2) . . ?
C27 C26 C25 108.3(2) . . ?
C30 C26 C25 112.1(3) . . ?
C30 C26 C27 108.3(2) . . ?
O5 C27 O6 119.2(3) . . ?
O5 C27 C26 124.1(3) . . ?
O6 C27 C26 116.6(3) . . ?
O6 C28 H28A 109.4 . . ?
O6 C28 H28B 109.4 . . ?
O6 C28 C29 111.3(3) . . ?
H28A C28 H28B 108.0 . . ?
C29 C28 H28A 109.4 . . ?
C29 C28 H28B 109.4 . . ?
C30 C29 C28 117.4(3) . . ?
C34 C29 C28 122.5(4) . . ?
C34 C29 C30 120.1(4) . . ?
C29 C30 C26 116.1(3) . . ?
C31 C30 C26 124.1(3) . . ?
C31 C30 C29 119.8(3) . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.1(4) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.0(4) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 120.0(4) . . ?
C34 C33 H33 120.0 . . ?
C29 C34 H34 120.0 . . ?
C33 C34 C29 119.9(4) . . ?
C33 C34 H34 120.0 . . ?
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 C7 1.212(4) . ?
O2 C10 1.206(4) . ?
O3 C10 1.338(4) . ?
O3 C11 1.457(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.380(5) . ?
C1 C6 1.391(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.409(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(5) . ?
C5 C6 1.390(4) . ?
C5 C9 1.526(4) . ?
C6 C7 1.475(5) . ?
C7 C8 1.525(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.578(4) . ?
C9 C10 1.544(4) . ?
C9 C13 1.528(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.507(5) . ?
C12 C13 1.391(4) . ?
C12 C17 1.389(5) . ?
C13 C14 1.395(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.397(5) . ?
C17 H17 0.9500 . ?
O4 C24 1.226(4) . ?
O5 C27 1.201(4) . ?
O6 C27 1.345(4) . ?
O6 C28 1.453(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.376(5) . ?
C18 C23 1.401(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.419(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.394(4) . ?
C22 C23 1.395(4) . ?
C22 C26 1.519(4) . ?
C23 C24 1.468(5) . ?
C24 C25 1.526(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.570(4) . ?
C26 C27 1.545(4) . ?
C26 C30 1.528(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.501(5) . ?
C29 C30 1.397(5) . ?
C29 C34 1.390(5) . ?
C30 C31 1.387(5) . ?
C31 H31 0.9500 . ?
C31 C32 1.393(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.390(7) . ?
C33 H33 0.9500 . ?
C33 C34 1.389(7) . ?
C34 H34 0.9500 . ?
