#------------------------------------------------------------------------------
#$Date: 2020-11-06 15:14:39 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/77/7157707.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_7157707
loop_
_publ_author_name
'Chen, Junrong'
'Li, Zhenmin'
'Suleman, Muhammad'
'Wang, Zaibin'
'Lu, Ping'
'Wang, Yanguang'
_publ_section_title
;
 TfOH-promoted synthesis of 4,5-dihydrooxazolo[5,4-c]isoquinolines
 via formal [3 + 2] cycloaddition of 4-diazoisoquinolin-3-one and
 benzonitriles.
;
_journal_issue                   38
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7671
_journal_page_last               7676
_journal_paper_doi               10.1039/d0ob01748e
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C16 H9 Cl N2 O'
_chemical_formula_sum            'C16 H9 Cl N2 O'
_chemical_formula_weight         280.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-11 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.854(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.757(10)
_cell_length_b                   4.748(2)
_cell_length_c                   23.677(10)
_cell_measurement_reflns_used    6809
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.79
_cell_volume                     2472.8(18)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18641
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.058
_diffrn_reflns_theta_min         2.778
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1587 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.9400.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0355P)²+2.6219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4372
_reflns_number_total             5370
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01748e2.cif
_cod_data_source_block           191224_cjr490177_1_c_0m
_cod_depositor_comments          'Adding full bibliography for 7157707.cif.'
_cod_original_cell_volume        2472.8(19)
_cod_database_code               7157707
_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   0.985
_shelx_estimated_absorpt_t_min   0.868
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C23(H23), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cl1 Cl 0.79384(2) 0.00298(12) 0.38645(2) 0.02914(13) Uani 1 1 d . . . . .
O1 O 0.55767(6) 1.1175(3) 0.45016(6) 0.0269(3) Uani 1 1 d . . . . .
N1 N 0.63765(9) 0.8283(4) 0.50606(8) 0.0318(4) Uani 1 1 d . . . . .
N2 N 0.56138(8) 0.9954(4) 0.35844(7) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.73196(9) 0.3359(5) 0.44352(9) 0.0247(4) Uani 1 1 d . . . . .
H1 H 0.757734 0.262863 0.478542 0.030 Uiso 1 1 calc R . . . .
C2 C 0.73805(9) 0.2488(4) 0.39019(9) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.70012(9) 0.3511(5) 0.33731(9) 0.0250(4) Uani 1 1 d . . . . .
H3 H 0.705139 0.284261 0.301014 0.030 Uiso 1 1 calc R . . . .
C4 C 0.65630(10) 0.5456(5) 0.33823(9) 0.0255(4) Uani 1 1 d . . . . .
H4 H 0.631138 0.615847 0.302621 0.031 Uiso 1 1 calc R . . . .
C5 C 0.64836(9) 0.6427(4) 0.39224(8) 0.0216(4) Uani 1 1 d . . . . .
C6 C 0.68640(9) 0.5375(5) 0.44559(9) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.67838(10) 0.6385(5) 0.49999(9) 0.0303(5) Uani 1 1 d . . . . .
H7 H 0.704379 0.563497 0.534682 0.036 Uiso 1 1 calc R . . . .
C8 C 0.60286(9) 0.9193(5) 0.45461(9) 0.0243(4) Uani 1 1 d . . . . .
C9 C 0.60496(9) 0.8437(4) 0.39909(8) 0.0220(4) Uani 1 1 d . . . . .
C10 C 0.53514(9) 1.1504(5) 0.39024(9) 0.0238(4) Uani 1 1 d . . . . .
C11 C 0.48645(9) 1.3540(5) 0.36938(9) 0.0245(4) Uani 1 1 d . . . . .
C12 C 0.46771(10) 1.4045(5) 0.30913(9) 0.0275(5) Uani 1 1 d . . . . .
H12 H 0.486247 1.306410 0.283265 0.033 Uiso 1 1 calc R . . . .
C13 C 0.42190(10) 1.5987(5) 0.28743(10) 0.0301(5) Uani 1 1 d . . . . .
H13 H 0.409091 1.633197 0.246589 0.036 Uiso 1 1 calc R . . . .
C14 C 0.39467(10) 1.7428(5) 0.32503(10) 0.0308(5) Uani 1 1 d . . . . .
H14 H 0.363391 1.875636 0.309866 0.037 Uiso 1 1 calc R . . . .
C15 C 0.41321(10) 1.6927(5) 0.38512(10) 0.0325(5) Uani 1 1 d . . . . .
H15 H 0.394681 1.791858 0.410861 0.039 Uiso 1 1 calc R . . . .
C16 C 0.45878(10) 1.4978(5) 0.40713(10) 0.0289(5) Uani 1 1 d . . . . .
H16 H 0.471177 1.462194 0.447953 0.035 Uiso 1 1 calc R . . . .
Cl2 Cl 1.09036(2) 1.51574(12) 0.60810(2) 0.03024(14) Uani 1 1 d . . . . .
O2 O 0.82256(6) 0.4162(3) 0.58888(6) 0.0255(3) Uani 1 1 d . . . . .
N3 N 0.85632(9) 0.7267(4) 0.52567(8) 0.0316(4) Uani 1 1 d . . . . .
N4 N 0.89171(7) 0.5060(4) 0.67459(7) 0.0218(3) Uani 1 1 d . . . . .
C17 C 0.99059(10) 1.1969(5) 0.56823(9) 0.0257(4) Uani 1 1 d . . . . .
H17 H 0.988531 1.280582 0.531328 0.031 Uiso 1 1 calc R . . . .
C18 C 1.03591(9) 1.2700(4) 0.61596(9) 0.0247(4) Uani 1 1 d . . . . .
C19 C 1.04013(9) 1.1506(5) 0.67171(9) 0.0263(4) Uani 1 1 d . . . . .
H19 H 1.072034 1.205449 0.704279 0.032 Uiso 1 1 calc R . . . .
C20 C 0.99803(9) 0.9558(5) 0.67847(9) 0.0252(4) Uani 1 1 d . . . . .
H20 H 1.000790 0.876166 0.715873 0.030 Uiso 1 1 calc R . . . .
C21 C 0.95042(9) 0.8723(4) 0.63009(8) 0.0219(4) Uani 1 1 d . . . . .
C22 C 0.94667(9) 0.9953(5) 0.57410(9) 0.0241(4) Uani 1 1 d . . . . .
C23 C 0.89898(10) 0.9152(5) 0.52487(9) 0.0311(5) Uani 1 1 d . . . . .
H23 H 0.897704 1.004103 0.488625 0.037 Uiso 1 1 calc R . . . .
C24 C 0.86213(9) 0.6172(5) 0.57857(9) 0.0240(4) Uani 1 1 d . . . . .
C25 C 0.90454(9) 0.6715(4) 0.63060(8) 0.0218(4) Uani 1 1 d . . . . .
C26 C 0.84368(9) 0.3616(5) 0.64789(8) 0.0224(4) Uani 1 1 d . . . . .
C27 C 0.80957(9) 0.1528(4) 0.67176(9) 0.0226(4) Uani 1 1 d . . . . .
C28 C 0.75980(9) 0.0132(5) 0.63554(9) 0.0254(4) Uani 1 1 d . . . . .
H28 H 0.747837 0.054081 0.594922 0.030 Uiso 1 1 calc R . . . .
C29 C 0.72782(10) -0.1858(5) 0.65907(10) 0.0294(5) Uani 1 1 d . . . . .
H29 H 0.694065 -0.280869 0.634549 0.035 Uiso 1 1 calc R . . . .
C30 C 0.74542(10) -0.2445(5) 0.71839(10) 0.0307(5) Uani 1 1 d . . . . .
H30 H 0.723670 -0.380489 0.734429 0.037 Uiso 1 1 calc R . . . .
C31 C 0.79477(10) -0.1055(5) 0.75457(10) 0.0311(5) Uani 1 1 d . . . . .
H31 H 0.806403 -0.146461 0.795197 0.037 Uiso 1 1 calc R . . . .
C32 C 0.82710(10) 0.0928(5) 0.73159(9) 0.0274(5) Uani 1 1 d . . . . .
H32 H 0.860870 0.186914 0.756310 0.033 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'
Cl Cl 0.1484 0.1585 '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
C8 O1 C10 103.17(15) . . ?
C7 N1 C8 112.71(18) . . ?
C10 N2 C9 104.10(17) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.85(18) . . ?
C6 C1 H1 120.6 . . ?
C1 C2 Cl1 119.76(16) . . ?
C1 C2 C3 122.0(2) . . ?
C3 C2 Cl1 118.21(16) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.14(19) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.94(19) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.83(19) . . ?
C9 C5 C4 125.42(19) . . ?
C9 C5 C6 114.74(18) . . ?
C1 C6 C5 119.21(18) . . ?
C1 C6 C7 121.32(18) . . ?
C5 C6 C7 119.47(19) . . ?
N1 C7 C6 125.44(19) . . ?
N1 C7 H7 117.3 . . ?
C6 C7 H7 117.3 . . ?
N1 C8 O1 122.97(18) . . ?
N1 C8 C9 128.8(2) . . ?
C9 C8 O1 108.26(17) . . ?
N2 C9 C5 131.71(18) . . ?
C8 C9 N2 109.41(18) . . ?
C8 C9 C5 118.87(18) . . ?
O1 C10 C11 118.06(18) . . ?
N2 C10 O1 115.05(18) . . ?
N2 C10 C11 126.88(18) . . ?
C12 C11 C10 117.72(19) . . ?
C16 C11 C10 122.38(19) . . ?
C16 C11 C12 119.9(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C24 O2 C26 103.64(15) . . ?
C23 N3 C24 112.42(18) . . ?
C26 N4 C25 104.10(16) . . ?
C18 C17 H17 120.2 . . ?
C18 C17 C22 119.54(19) . . ?
C22 C17 H17 120.2 . . ?
C17 C18 Cl2 119.19(17) . . ?
C17 C18 C19 121.7(2) . . ?
C19 C18 Cl2 119.09(16) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.5(2) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 119.10(19) . . ?
C25 C21 C20 126.45(19) . . ?
C25 C21 C22 114.44(18) . . ?
C17 C22 C21 119.41(19) . . ?
C17 C22 C23 120.57(19) . . ?
C23 C22 C21 120.03(19) . . ?
N3 C23 C22 125.2(2) . . ?
N3 C23 H23 117.4 . . ?
C22 C23 H23 117.4 . . ?
O2 C24 C25 108.12(17) . . ?
N3 C24 O2 121.75(18) . . ?
N3 C24 C25 130.1(2) . . ?
N4 C25 C21 132.99(18) . . ?
C24 C25 N4 109.20(18) . . ?
C24 C25 C21 117.81(18) . . ?
O2 C26 C27 115.96(17) . . ?
N4 C26 O2 114.95(18) . . ?
N4 C26 C27 129.09(18) . . ?
C28 C27 C26 120.78(19) . . ?
C32 C27 C26 119.25(19) . . ?
C32 C27 C28 120.0(2) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 120.0(2) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.8(2) . . ?
C30 C29 H29 120.1 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.4(2) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 119.8 . . ?
C32 C31 C30 120.3(2) . . ?
C32 C31 H31 119.8 . . ?
C27 C32 H32 120.2 . . ?
C31 C32 C27 119.5(2) . . ?
C31 C32 H32 120.2 . . ?
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
Cl1 C2 1.743(2) . ?
O1 C8 1.378(3) . ?
O1 C10 1.388(2) . ?
N1 C7 1.327(3) . ?
N1 C8 1.343(3) . ?
N2 C9 1.393(3) . ?
N2 C10 1.302(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.369(3) . ?
C1 C6 1.421(3) . ?
C2 C3 1.412(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.363(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.414(3) . ?
C5 C6 1.426(3) . ?
C5 C9 1.412(3) . ?
C6 C7 1.429(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.375(3) . ?
C10 C11 1.458(3) . ?
C11 C12 1.401(3) . ?
C11 C16 1.397(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.397(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
Cl2 C18 1.746(2) . ?
O2 C24 1.376(3) . ?
O2 C26 1.381(2) . ?
N3 C23 1.324(3) . ?
N3 C24 1.331(3) . ?
N4 C25 1.394(3) . ?
N4 C26 1.308(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.365(3) . ?
C17 C22 1.416(3) . ?
C18 C19 1.417(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.370(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.417(3) . ?
C21 C22 1.431(3) . ?
C21 C25 1.416(3) . ?
C22 C23 1.426(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(3) . ?
C26 C27 1.459(3) . ?
C27 C28 1.400(3) . ?
C27 C32 1.399(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.393(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.387(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.392(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.389(3) . ?
C32 H32 0.9500 . ?
