#------------------------------------------------------------------------------
#$Date: 2021-01-07 06:34:59 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260617 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/71/7127199.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_7127199
loop_
_publ_author_name
'Zhao, Peng'
'Yu, Xiao-Xiao'
'Zhou, You'
'Huang, Chun'
'Wu, Yan-Dong'
'Zhu, Yan-Ping'
'Wu, An-Xin'
_publ_section_title
;
 Arylacetylenes as two-carbon synthons: synthesis of eight-membered rings
 via C[triple bond, length as m-dash]C bond cleavage.
;
_journal_issue                   83
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              12554
_journal_page_last               12557
_journal_paper_doi               10.1039/d0cc05363e
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C22 H18 N2 O'
_chemical_formula_sum            'C22 H18 N2 O'
_chemical_formula_weight         326.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-19
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2020-08-05 deposited with the CCDC.	2020-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.361(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.602(3)
_cell_length_b                   13.685(3)
_cell_length_c                   19.401(4)
_cell_measurement_reflns_used    6724
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.22
_cell_measurement_theta_min      2.26
_cell_volume                     3563.3(13)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12571
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.125
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0103(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0486
_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)+(0.0825P)²+2.1671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2732
_reflns_number_total             3323
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc05363e2.cif
_cod_data_source_block           y
_cod_depositor_comments
'Adding full bibliography for 7127198--7127199.cif.'
_cod_original_cell_volume        3563.2(12)
_cod_database_code               7127199
_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   0.989
_shelx_estimated_absorpt_t_min   0.985
_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: 
 C3(H3), C4(H4), C7(H7), C10(H10), C12(H12), C13(H13), C18(H18), C19(H19), 
 C20(H20), C21(H21), C22(H22), N1(H1) 
2.b Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C) 
;
_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'
'-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
C1 C 0.64194(16) 0.54293(16) 0.30753(12) 0.0646(6) Uani 1 1 d . . . . .
H1A H 0.6585 0.4798 0.3276 0.097 Uiso 1 1 calc GR . . . .
H1B H 0.7003 0.5835 0.3140 0.097 Uiso 1 1 calc GR . . . .
H1C H 0.6174 0.5359 0.2585 0.097 Uiso 1 1 calc GR . . . .
C2 C 0.56287(13) 0.58943(12) 0.34284(9) 0.0454(4) Uani 1 1 d . . . . .
C3 C 0.50023(16) 0.53421(13) 0.37699(11) 0.0594(5) Uani 1 1 d . . . . .
H3 H 0.5093 0.4669 0.3804 0.071 Uiso 1 1 calc R . . . .
C4 C 0.42444(16) 0.57701(13) 0.40608(12) 0.0563(5) Uani 1 1 d . . . . .
H4 H 0.3825 0.5383 0.4280 0.068 Uiso 1 1 calc R . . . .
C5 C 0.41077(12) 0.67746(12) 0.40264(8) 0.0388(4) Uani 1 1 d . . . . .
C6 C 0.47585(11) 0.73498(11) 0.37236(8) 0.0346(4) Uani 1 1 d . . . . .
C7 C 0.55019(12) 0.68995(12) 0.34191(9) 0.0392(4) Uani 1 1 d . . . . .
H7 H 0.5925 0.7286 0.3203 0.047 Uiso 1 1 calc R . . . .
C8 C 0.25541(12) 0.77069(12) 0.39540(9) 0.0405(4) Uani 1 1 d . . . . .
C9 C 0.25483(12) 0.79100(13) 0.31923(9) 0.0432(4) Uani 1 1 d . . . . .
C10 C 0.17513(14) 0.75648(17) 0.27152(11) 0.0604(5) Uani 1 1 d . . . . .
H10 H 0.1290 0.7151 0.2870 0.072 Uiso 1 1 calc R . . . .
C11 C 0.16231(16) 0.7822(2) 0.20110(12) 0.0731(7) Uani 1 1 d . . . . .
C12 C 0.22919(18) 0.8469(2) 0.18043(11) 0.0737(7) Uani 1 1 d . . . . .
H12 H 0.2214 0.8661 0.1339 0.088 Uiso 1 1 calc R . . . .
C13 C 0.30704(15) 0.88361(16) 0.22686(10) 0.0580(5) Uani 1 1 d . . . . .
H13 H 0.3496 0.9291 0.2116 0.070 Uiso 1 1 calc R . . . .
C14 C 0.32363(12) 0.85409(12) 0.29647(9) 0.0424(4) Uani 1 1 d . . . . .
C15 C 0.0765(2) 0.7405(3) 0.15008(17) 0.1246(15) Uani 1 1 d . . . . .
H15A H 0.0741 0.6710 0.1560 0.187 Uiso 1 1 calc GR . . . .
H15B H 0.0858 0.7553 0.1032 0.187 Uiso 1 1 calc GR . . . .
H15C H 0.0151 0.7689 0.1587 0.187 Uiso 1 1 calc GR . . . .
C16 C 0.47147(12) 0.84456(11) 0.37634(8) 0.0374(4) Uani 1 1 d . . . . .
C17 C 0.55418(13) 0.89382(12) 0.42312(9) 0.0420(4) Uani 1 1 d . . . . .
C18 C 0.56394(16) 0.99521(13) 0.42074(11) 0.0584(5) Uani 1 1 d . . . . .
H18 H 0.5187 1.0318 0.3900 0.070 Uiso 1 1 calc R . . . .
C19 C 0.64103(19) 1.04148(17) 0.46423(13) 0.0736(7) Uani 1 1 d . . . . .
H19 H 0.6472 1.1090 0.4621 0.088 Uiso 1 1 calc R . . . .
C20 C 0.70787(18) 0.98944(18) 0.51004(13) 0.0713(7) Uani 1 1 d . . . . .
H20 H 0.7594 1.0213 0.5387 0.086 Uiso 1 1 calc R . . . .
C21 C 0.69859(17) 0.89030(18) 0.51352(12) 0.0681(6) Uani 1 1 d . . . . .
H21 H 0.7437 0.8546 0.5449 0.082 Uiso 1 1 calc R . . . .
C22 C 0.62190(14) 0.84248(14) 0.47022(10) 0.0536(5) Uani 1 1 d . . . . .
H22 H 0.6162 0.7749 0.4731 0.064 Uiso 1 1 calc R . . . .
N1 N 0.33162(11) 0.72125(10) 0.43185(7) 0.0430(4) Uani 1 1 d . . . . .
H1 H 0.3330 0.7155 0.4761 0.052 Uiso 1 1 calc R . . . .
N2 N 0.40314(11) 0.89729(10) 0.34179(8) 0.0435(4) Uani 1 1 d . . . . .
O1 O 0.18422(9) 0.79883(9) 0.42266(7) 0.0505(4) 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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.80(17) . . ?
C3 C2 C7 117.55(15) . . ?
C7 C2 C1 120.65(17) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.41(16) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.19(16) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 N1 120.05(15) . . ?
C6 C5 C4 119.59(15) . . ?
C6 C5 N1 120.34(14) . . ?
C5 C6 C7 119.08(14) . . ?
C5 C6 C16 120.80(13) . . ?
C7 C6 C16 119.99(14) . . ?
C2 C7 C6 122.02(15) . . ?
C2 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
N1 C8 C9 119.50(14) . . ?
O1 C8 C9 118.91(15) . . ?
O1 C8 N1 121.58(15) . . ?
C10 C9 C8 118.12(16) . . ?
C10 C9 C14 119.34(17) . . ?
C14 C9 C8 121.92(15) . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C15 120.4(3) . . ?
C12 C11 C10 117.7(2) . . ?
C12 C11 C15 121.9(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C9 C14 N2 123.25(15) . . ?
C13 C14 C9 118.35(18) . . ?
C13 C14 N2 118.07(17) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C6 116.82(14) . . ?
N2 C16 C6 124.63(15) . . ?
N2 C16 C17 118.54(14) . . ?
C18 C17 C16 119.81(17) . . ?
C22 C17 C16 122.05(15) . . ?
C22 C17 C18 118.13(17) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(2) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.6(2) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 120.96(19) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C5 N1 H1 117.6 . . ?
C8 N1 C5 124.85(14) . . ?
C8 N1 H1 117.6 . . ?
C16 N2 C14 120.65(14) . . ?
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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.507(2) . ?
C2 C3 1.386(3) . ?
C2 C7 1.386(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(2) . ?
C5 C6 1.385(2) . ?
C5 N1 1.427(2) . ?
C6 C7 1.395(2) . ?
C6 C16 1.503(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.502(2) . ?
C8 N1 1.339(2) . ?
C8 O1 1.2378(19) . ?
C9 C10 1.389(3) . ?
C9 C14 1.397(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.394(3) . ?
C11 C12 1.375(4) . ?
C11 C15 1.514(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(3) . ?
C14 N2 1.408(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.487(2) . ?
C16 N2 1.277(2) . ?
C17 C18 1.395(2) . ?
C17 C22 1.380(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.364(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.365(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.392(3) . ?
C22 H22 0.9300 . ?
N1 H1 0.8600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -176.5(2) . . . . ?
C1 C2 C7 C6 178.13(16) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C2 C7 C6 -1.6(3) . . . . ?
C3 C4 C5 C6 -2.5(3) . . . . ?
C3 C4 C5 N1 179.12(18) . . . . ?
C4 C5 C6 C7 4.0(2) . . . . ?
C4 C5 C6 C16 -171.78(17) . . . . ?
C4 C5 N1 C8 -117.3(2) . . . . ?
C5 C6 C7 C2 -2.0(2) . . . . ?
C5 C6 C16 C17 108.25(17) . . . . ?
C5 C6 C16 N2 -72.9(2) . . . . ?
C6 C5 N1 C8 64.4(2) . . . . ?
C6 C16 C17 C18 169.44(15) . . . . ?
C6 C16 C17 C22 -11.5(2) . . . . ?
C6 C16 N2 C14 0.8(2) . . . . ?
C7 C2 C3 C4 3.2(3) . . . . ?
C7 C6 C16 C17 -67.54(19) . . . . ?
C7 C6 C16 N2 111.31(18) . . . . ?
C8 C9 C10 C11 171.90(17) . . . . ?
C8 C9 C14 C13 -168.00(15) . . . . ?
C8 C9 C14 N2 5.2(2) . . . . ?
C9 C8 N1 C5 -5.8(2) . . . . ?
C9 C10 C11 C12 -2.8(3) . . . . ?
C9 C10 C11 C15 178.0(2) . . . . ?
C9 C14 N2 C16 63.0(2) . . . . ?
C10 C9 C14 C13 2.8(2) . . . . ?
C10 C9 C14 N2 176.04(15) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
C11 C12 C13 C14 2.3(3) . . . . ?
C12 C13 C14 C9 -4.4(3) . . . . ?
C12 C13 C14 N2 -177.94(16) . . . . ?
C13 C14 N2 C16 -123.81(17) . . . . ?
C14 C9 C10 C11 0.7(3) . . . . ?
C15 C11 C12 C13 -179.5(2) . . . . ?
C16 C6 C7 C2 173.89(16) . . . . ?
C16 C17 C18 C19 -179.94(16) . . . . ?
C16 C17 C22 C21 -179.90(17) . . . . ?
C17 C16 N2 C14 179.59(13) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C17 C22 C21 -0.8(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 C17 0.1(3) . . . . ?
C22 C17 C18 C19 1.0(3) . . . . ?
N1 C5 C6 C7 -177.61(15) . . . . ?
N1 C5 C6 C16 6.6(2) . . . . ?
N1 C8 C9 C10 121.51(18) . . . . ?
N1 C8 C9 C14 -67.6(2) . . . . ?
N2 C16 C17 C18 -9.5(2) . . . . ?
N2 C16 C17 C22 169.57(16) . . . . ?
O1 C8 C9 C10 -57.3(2) . . . . ?
O1 C8 C9 C14 113.65(18) . . . . ?
O1 C8 N1 C5 172.97(15) . . . . ?
