#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:15:21 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/06/7240674.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_7240674
loop_
_publ_author_name
'Chen, Qinfang'
'Pan, Yihao'
'Zhao, Dongxin'
'Yang, Weiran'
'Zheng, Jing'
_publ_section_title
;
 Construct indeno[1,2-b]oxepine or cis-cyclopropylacrylate by sulfur
 ylides
;
_journal_issue                   37
_journal_name_full               'RSC Advances'
_journal_page_first              21895
_journal_page_last               21906
_journal_paper_doi               10.1039/D0RA03919E
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C17 H13 N3 O2'
_chemical_formula_sum            'C17 H13 N3 O2'
_chemical_formula_weight         291.30
_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     dual
_audit_creation_date             2019-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-26 deposited with the CCDC.	2020-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.896(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.1711(17)
_cell_length_b                   10.0725(7)
_cell_length_c                   11.4469(8)
_cell_measurement_reflns_used    5264
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      55.07
_cell_measurement_theta_min      4.093
_cell_volume                     3017.1(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      169.99
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15336
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.395
_diffrn_reflns_theta_min         2.938
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1621 before and 0.0735 after correction. The Ratio of minimum to maximum transmission is 0.7724. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0718
_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)+(0.1018P)²+4.8570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1836
_refine_ls_wR_factor_ref         0.2159
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1900
_reflns_number_total             2904
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra03919e2.cif
_cod_data_source_block           1905060293_0m
_cod_depositor_comments
'Adding full bibliography for 7240673--7240674.cif.'
_cod_database_code               7240674
_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   0.978
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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
O1 O 0.54856(10) 0.1179(3) 0.3466(2) 0.0722(8) Uani 1 1 d . . . . .
O2 O 0.51176(10) 0.2886(3) 0.4418(3) 0.0810(9) Uani 1 1 d . . . . .
N1 N 0.40757(12) 0.2329(3) 0.7784(2) 0.0579(8) Uani 1 1 d . . . . .
N2 N 0.31093(13) -0.1163(3) 0.7279(3) 0.0638(8) Uani 1 1 d . . . . .
N3 N 0.30539(11) 0.8128(3) 0.4355(3) 0.0565(8) Uani 1 1 d . . . . .
C1 C 0.33138(11) 0.1432(3) 0.5256(2) 0.0399(7) Uani 1 1 d . . . . .
H1 H 0.300363 0.093358 0.498325 0.048 Uiso 1 1 calc R . . . .
C2 C 0.35771(12) 0.0817(3) 0.6331(3) 0.0407(7) Uani 1 1 d . . . . .
C3 C 0.38011(11) 0.0688(3) 0.5095(2) 0.0400(7) Uani 1 1 d . . . . .
H3 H 0.376668 -0.020580 0.472223 0.048 Uiso 1 1 calc R . . . .
C4 C 0.42831(12) 0.1397(3) 0.4871(3) 0.0422(7) Uani 1 1 d . . . . .
H4 H 0.433878 0.222521 0.524865 0.051 Uiso 1 1 calc R . . . .
C5 C 0.46435(12) 0.0943(3) 0.4172(3) 0.0471(8) Uani 1 1 d . . . . .
H5 H 0.458803 0.011822 0.378766 0.057 Uiso 1 1 calc R . . . .
C6 C 0.51232(14) 0.1652(4) 0.3965(3) 0.0565(9) Uani 1 1 d . . . . .
C7 C 0.55898(18) 0.3655(5) 0.4405(6) 0.118(2) Uani 1 1 d . . . . .
H7A H 0.565128 0.404291 0.518982 0.141 Uiso 1 1 calc R . . . .
H7B H 0.587858 0.305459 0.423498 0.141 Uiso 1 1 calc R . . . .
C8 C 0.55773(19) 0.4665(5) 0.3587(5) 0.1039(18) Uani 1 1 d . . . . .
H8A H 0.555885 0.428187 0.280082 0.156 Uiso 1 1 calc GR . . . .
H8B H 0.588746 0.520418 0.366792 0.156 Uiso 1 1 calc GR . . . .
H8C H 0.527665 0.522363 0.371359 0.156 Uiso 1 1 calc GR . . . .
C9 C 0.38529(12) 0.1662(3) 0.7144(3) 0.0429(7) Uani 1 1 d . . . . .
C10 C 0.33260(13) -0.0304(3) 0.6861(3) 0.0468(8) Uani 1 1 d . . . . .
C11 C 0.32688(11) 0.2902(3) 0.5110(2) 0.0383(7) Uani 1 1 d . . . . .
C12 C 0.34499(12) 0.3502(3) 0.4104(3) 0.0434(7) Uani 1 1 d . . . . .
H12 H 0.361639 0.298119 0.353264 0.052 Uiso 1 1 calc R . . . .
C13 C 0.33898(12) 0.4850(3) 0.3930(3) 0.0442(8) Uani 1 1 d . . . . .
H13 H 0.351797 0.525557 0.324493 0.053 Uiso 1 1 calc R . . . .
C14 C 0.31406(11) 0.5613(3) 0.4760(3) 0.0409(7) Uani 1 1 d . . . . .
C15 C 0.29573(12) 0.5021(3) 0.5771(3) 0.0445(7) Uani 1 1 d . . . . .
H15 H 0.278946 0.554182 0.634097 0.053 Uiso 1 1 calc R . . . .
C16 C 0.30211(11) 0.3678(3) 0.5938(3) 0.0422(7) Uani 1 1 d . . . . .
H16 H 0.289491 0.327404 0.662545 0.051 Uiso 1 1 calc R . . . .
C17 C 0.30847(12) 0.7020(3) 0.4553(3) 0.0454(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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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
C6 O2 C7 118.2(4) . . ?
C2 C1 H1 113.6 . . ?
C3 C1 H1 113.6 . . ?
C3 C1 C2 61.44(19) . . ?
C3 C1 C11 123.3(2) . . ?
C11 C1 H1 113.6 . . ?
C11 C1 C2 121.6(2) . . ?
C1 C2 C3 58.02(18) . . ?
C9 C2 C1 119.5(2) . . ?
C9 C2 C3 116.5(3) . . ?
C10 C2 C1 116.8(3) . . ?
C10 C2 C3 120.0(2) . . ?
C10 C2 C9 114.6(3) . . ?
C1 C3 C2 60.53(19) . . ?
C1 C3 H3 115.7 . . ?
C2 C3 H3 115.7 . . ?
C4 C3 C1 120.9(2) . . ?
C4 C3 C2 117.1(2) . . ?
C4 C3 H3 115.7 . . ?
C3 C4 H4 118.1 . . ?
C5 C4 C3 123.8(3) . . ?
C5 C4 H4 118.1 . . ?
C4 C5 H5 118.4 . . ?
C4 C5 C6 123.2(3) . . ?
C6 C5 H5 118.4 . . ?
O1 C6 O2 123.8(3) . . ?
O1 C6 C5 124.3(4) . . ?
O2 C6 C5 111.9(3) . . ?
O2 C7 H7A 109.0 . . ?
O2 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 O2 112.7(4) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C2 179.4(4) . . ?
N2 C10 C2 177.2(4) . . ?
C12 C11 C1 119.7(3) . . ?
C12 C11 C16 119.1(3) . . ?
C16 C11 C1 121.1(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 C17 118.5(3) . . ?
C15 C14 C17 121.4(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H15 120.2 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 H16 119.6 . . ?
N3 C17 C14 177.3(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 C6 1.212(4) . ?
O2 C6 1.347(5) . ?
O2 C7 1.459(5) . ?
N1 C9 1.147(4) . ?
N2 C10 1.143(4) . ?
N3 C17 1.142(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.532(4) . ?
C1 C3 1.493(4) . ?
C1 C11 1.494(4) . ?
C2 C3 1.546(4) . ?
C2 C9 1.446(4) . ?
C2 C10 1.445(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.475(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.327(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.467(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.382(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C11 C12 1.391(4) . ?
C11 C16 1.396(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(4) . ?
C14 C15 1.393(4) . ?
C14 C17 1.444(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(4) . ?
C16 H16 0.9500 . ?
