#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:36:45 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284285 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/64/7246413.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_7246413
loop_
_publ_author_name
'Wu, Jianglong'
'Ma, Yinfeng'
'Wang, Yan'
'Wang, Chenyu'
'Luo, Hui'
'Li, Dianjun'
'Yang, Jinhui'
_publ_section_title
;
 Copper-catalyzed direct synthesis of 3-methylene-2-arylisoindolin-1-ones
 with calcium carbide as a surrogate of gaseous acetylene
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              3425
_journal_page_last               3430
_journal_paper_doi               10.1039/D2GC03572C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C15 H10 I N O'
_chemical_formula_sum            'C15 H10 I N O'
_chemical_formula_weight         347.14
_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             2022-07-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-01-19 deposited with the CCDC.	2023-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.381(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0551(6)
_cell_length_b                   7.4021(3)
_cell_length_c                   13.9932(6)
_cell_measurement_reflns_used    7995
_cell_measurement_temperature    300.0
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.97
_cell_volume                     1325.65(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12688
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.578
_diffrn_reflns_theta_min         1.591
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.402
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1627 before and 0.0371 after correction.
The Ratio of minimum to maximum transmission is 0.8340.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.922
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0270
_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)+(0.0601P)²+1.2726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2437
_reflns_number_total             2735
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc03572c2.cif
_cod_data_source_block           wjl-1
_cod_depositor_comments          'Adding full bibliography for 7246413.cif.'
_cod_database_code               7246413
_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   0.778
_shelx_estimated_absorpt_t_min   0.658
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14)
2.b X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_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
C C 0.7561(2) 0.4478(3) 0.4793(2) 0.0403(6) Uani 1 1 d . . . . .
C2 C 0.8583(2) 0.4484(4) 0.5451(2) 0.0403(6) Uani 1 1 d . . . . .
C3 C 0.9239(3) 0.5892(4) 0.5831(2) 0.0493(7) Uani 1 1 d . . . . .
H3 H 0.905240 0.708803 0.568721 0.059 Uiso 1 1 calc R U . . .
C4 C 1.0179(3) 0.5457(5) 0.6432(3) 0.0573(9) Uani 1 1 d . . . . .
H4 H 1.063088 0.638282 0.669192 0.069 Uiso 1 1 calc R U . . .
C5 C 1.0469(3) 0.3688(6) 0.6659(3) 0.0628(9) Uani 1 1 d . . . . .
H5 H 1.111052 0.344458 0.706107 0.075 Uiso 1 1 calc R U . . .
C6 C 0.9813(3) 0.2278(5) 0.6292(3) 0.0558(8) Uani 1 1 d . . . . .
H6 H 1.000026 0.108454 0.644509 0.067 Uiso 1 1 calc R U . . .
C7 C 0.8867(2) 0.2702(4) 0.5689(2) 0.0433(6) Uani 1 1 d . . . . .
C8 C 0.8017(3) 0.1507(4) 0.5226(2) 0.0472(7) Uani 1 1 d . . . . .
O9 O 0.7934(2) -0.0120(3) 0.5290(2) 0.0683(8) Uani 1 1 d . . . . .
C10 C 0.6276(2) 0.2004(4) 0.4191(2) 0.0434(6) Uani 1 1 d . . . . .
C11 C 0.5395(3) 0.2347(5) 0.4585(3) 0.0541(8) Uani 1 1 d . . . . .
H11 H 0.545611 0.302251 0.515358 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4428(3) 0.1683(5) 0.4131(3) 0.0628(9) Uani 1 1 d . . . . .
H12 H 0.383807 0.193750 0.438666 0.075 Uiso 1 1 calc R U . . .
C13 C 0.4341(3) 0.0651(5) 0.3304(3) 0.0626(10) Uani 1 1 d . . . . .
H13 H 0.369383 0.018121 0.301230 0.075 Uiso 1 1 calc R U . . .
C14 C 0.5200(3) 0.0304(5) 0.2901(3) 0.0566(8) Uani 1 1 d . . . . .
H14 H 0.513529 -0.040346 0.234336 0.068 Uiso 1 1 calc R U . . .
C15 C 0.6169(2) 0.1019(4) 0.3334(2) 0.0448(7) Uani 1 1 d . . . . .
I1 I 0.74211(2) 0.06423(4) 0.26254(2) 0.06537(14) Uani 1 1 d . . . . .
N1 N 0.7264(2) 0.2632(3) 0.46906(19) 0.0438(6) Uani 1 1 d . . . . .
C1 C 0.7022(3) 0.5849(4) 0.4353(3) 0.0530(8) Uani 1 1 d . . . . .
H1A H 0.638627 0.564561 0.393172 0.064 Uiso 1 1 calc R U . . .
H1B H 0.727601 0.701961 0.446244 0.064 Uiso 1 1 calc R U . . .
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'
I I -0.4742 1.8119 '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
N1 C C2 105.3(2) . . ?
C1 C C2 129.0(3) . . ?
C1 C N1 125.7(3) . . ?
C3 C2 C 131.4(3) . . ?
C3 C2 C7 120.3(3) . . ?
C7 C2 C 108.3(2) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 C2 117.8(3) . . ?
C4 C3 H3 121.1 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 122.0(3) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 121.1 . . ?
C7 C6 C5 117.8(3) . . ?
C7 C6 H6 121.1 . . ?
C2 C7 C8 108.8(3) . . ?
C6 C7 C2 121.6(3) . . ?
C6 C7 C8 129.6(3) . . ?
O9 C8 C7 129.5(3) . . ?
O9 C8 N1 124.8(3) . . ?
N1 C8 C7 105.7(2) . . ?
C11 C10 N1 119.2(3) . . ?
C15 C10 C11 119.2(3) . . ?
C15 C10 N1 121.6(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C10 C15 C14 120.2(3) . . ?
C10 C15 I1 121.7(2) . . ?
C14 C15 I1 118.0(3) . . ?
C8 N1 C 111.8(3) . . ?
C8 N1 C10 123.2(2) . . ?
C10 N1 C 124.7(2) . . ?
C C1 H1A 120.0 . . ?
C C1 H1B 120.0 . . ?
H1A C1 H1B 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
C C2 1.463(4) . ?
C N1 1.420(3) . ?
C C1 1.317(4) . ?
C2 C3 1.387(4) . ?
C2 C7 1.393(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(4) . ?
C7 C8 1.467(4) . ?
C8 O9 1.214(4) . ?
C8 N1 1.389(4) . ?
C10 C11 1.393(5) . ?
C10 C15 1.387(4) . ?
C10 N1 1.418(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.395(5) . ?
C15 I1 2.091(3) . ?
C1 H1A 0.9300 . ?
C1 H1B 0.9300 . ?
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
C C2 C3 C4 -179.0(3) . . . . ?
C C2 C7 C6 178.8(3) . . . . ?
C C2 C7 C8 -2.5(4) . . . . ?
C2 C N1 C8 -0.2(4) . . . . ?
C2 C N1 C10 173.4(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C2 C7 C8 O9 -176.0(4) . . . . ?
C2 C7 C8 N1 2.3(4) . . . . ?
C3 C2 C7 C6 -1.3(5) . . . . ?
C3 C2 C7 C8 177.4(3) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C4 C5 C6 C7 0.5(6) . . . . ?
C5 C6 C7 C2 0.4(5) . . . . ?
C5 C6 C7 C8 -178.0(3) . . . . ?
C6 C7 C8 O9 2.6(6) . . . . ?
C6 C7 C8 N1 -179.1(3) . . . . ?
C7 C2 C3 C4 1.2(5) . . . . ?
C7 C8 N1 C -1.3(4) . . . . ?
C7 C8 N1 C10 -175.0(3) . . . . ?
O9 C8 N1 C 177.2(3) . . . . ?
O9 C8 N1 C10 3.4(5) . . . . ?
C10 C11 C12 C13 1.5(6) . . . . ?
C11 C10 C15 C14 -3.3(5) . . . . ?
C11 C10 C15 I1 174.3(2) . . . . ?
C11 C10 N1 C -68.6(4) . . . . ?
C11 C10 N1 C8 104.3(4) . . . . ?
C11 C12 C13 C14 -1.8(6) . . . . ?
C12 C13 C14 C15 -0.4(6) . . . . ?
C13 C14 C15 C10 3.0(5) . . . . ?
C13 C14 C15 I1 -174.7(3) . . . . ?
C15 C10 C11 C12 1.1(5) . . . . ?
C15 C10 N1 C 113.0(4) . . . . ?
C15 C10 N1 C8 -74.1(4) . . . . ?
N1 C C2 C3 -178.2(3) . . . . ?
N1 C C2 C7 1.6(3) . . . . ?
N1 C10 C11 C12 -177.4(3) . . . . ?
N1 C10 C15 C14 175.1(3) . . . . ?
N1 C10 C15 I1 -7.3(4) . . . . ?
C1 C C2 C3 3.6(6) . . . . ?
C1 C C2 C7 -176.5(4) . . . . ?
C1 C N1 C8 178.0(3) . . . . ?
C1 C N1 C10 -8.4(5) . . . . ?
